data_grec3005
_audit_update_record
;
2013-06-04 # Formatted by publCIF
;
#----------------------------------------------------------------------------#
# CRYSTALLOGRAPHER #
#----------------------------------------------------------------------------#
# Dr. Olivier Blacque
# X-ray Crystallography Facility
# University of Z\"urich
# Winterthurerstrasse 190
# CH-8057 Z\"urich
# e-mail: oblacque@aci.uzh.ch
# Fax: +41 (0)446356802
# Tel: +41 (0)446354651
#----------------------------------------------------------------------------#
_publ_section_title
;
(C~31~H~39~N~2~)^+^.Cl^-^, CH~2~Cl~2~
;
_publ_section_abstract
;
X-ray crystal structure determination of the title compound,
(C~31~H~39~N~2~)^+^.Cl^-^, CH~2~Cl~2~ (GREC3005_2013)
;
loop_
_publ_author_name
_publ_author_address
'Single crystals from Gabriele Grieco (Ph.D. student)'
;
Prof. Dr. em. Heinz Berke
Institute of Inorganic Chemistry,
Winterthurerstrasse 190,
CH-8057, Zuerich, Switzerland
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C31 H39 N2, C H2 Cl2, Cl'
_chemical_formula_sum 'C32 H41 Cl3 N2'
_chemical_formula_weight 560.02
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 12.6905(3)
_cell_length_b 18.5911(3)
_cell_length_c 14.3067(4)
_cell_angle_alpha 90.00
_cell_angle_beta 113.687(3)
_cell_angle_gamma 90.00
_cell_volume 3091.02(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 183(2)
_cell_measurement_reflns_used 17149
_cell_measurement_theta_min 2.19
_cell_measurement_theta_max 30.38
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.203
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1192
_exptl_absorpt_coefficient_mu 2.843
_exptl_absorpt_correction_T_min 0.840
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Version 1.171.36.20 (Agilent Technologies, 2012)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
?
_diffrn_ambient_temperature 183(1)
_diffrn_radiation_wavelength 1.5418
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator 'mirror'
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector 'Atlas CCD camera on \k goniostat'
_diffrn_measurement_method '\w scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 40306
_diffrn_reflns_av_R_equivalents 0.0323
_diffrn_reflns_av_sigmaI/netI 0.0199
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 4.76
_diffrn_reflns_theta_max 89.47
_reflns_number_total 7060
_reflns_number_gt 6190
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, version 1.171.36.24a (Agilent Technologies, 2012)
;
_computing_cell_refinement
;
CrysAlisPro, version 1.171.36.20 (Agilent Technologies, 2012)
;
_computing_data_reduction
;
CrysAlisPro, version 1.171.36.20 (Agilent Technologies, 2012)
;
_computing_structure_solution
; SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
; SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and/or Mercury (Macrae et
al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999), PLATON for Windows (Spek, 2003) and
publCIF (Westrip, 2010)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1154P)^2^+3.6728P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7060
_refine_ls_number_parameters 346
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0850
_refine_ls_R_factor_gt 0.0777
_refine_ls_wR_factor_ref 0.2142
_refine_ls_wR_factor_gt 0.2073
_refine_ls_goodness_of_fit_ref 1.077
_refine_ls_restrained_S_all 1.077
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62531(17) 0.12534(12) 0.29838(15) 0.0194(4) Uani 1 1 d . . .
C2 C 0.68425(18) 0.01240(12) 0.30440(16) 0.0210(4) Uani 1 1 d . . .
C3 C 0.7466(2) -0.05055(13) 0.3133(2) 0.0302(5) Uani 1 1 d . . .
H3 H 0.8264 -0.0505 0.3363 0.036 Uiso 1 1 calc R . .
C4 C 0.6830(3) -0.11333(14) 0.2859(2) 0.0381(6) Uani 1 1 d . . .
H4 H 0.7210 -0.1567 0.2898 0.046 Uiso 1 1 calc R . .
C5 C 0.5628(2) -0.11349(14) 0.2524(2) 0.0351(6) Uani 1 1 d . . .
H5 H 0.5238 -0.1571 0.2360 0.042 Uiso 1 1 calc R . .
C6 C 0.5006(2) -0.05097(13) 0.24295(19) 0.0292(5) Uani 1 1 d . . .
H6 H 0.4209 -0.0509 0.2204 0.035 Uiso 1 1 calc R . .
C7 C 0.56530(18) 0.01208(12) 0.26950(16) 0.0209(4) Uani 1 1 d . . .
C8 C 0.83551(18) 0.11084(12) 0.36317(17) 0.0219(4) Uani 1 1 d . . .
C9 C 0.89246(19) 0.11589(12) 0.46920(18) 0.0237(4) Uani 1 1 d . . .
C10 C 1.0029(2) 0.14554(13) 0.50733(19) 0.0282(5) Uani 1 1 d . . .
H10 H 1.0436 0.1505 0.5774 0.034 Uiso 1 1 calc R . .
C11 C 1.0520(2) 0.16758(14) 0.4415(2) 0.0330(5) Uani 1 1 d . . .
H11 H 1.1251 0.1879 0.4680 0.040 Uiso 1 1 calc R . .
C12 C 0.9940(2) 0.15991(14) 0.3372(2) 0.0320(5) Uani 1 1 d . . .
H12 H 1.0293 0.1744 0.2945 0.038 Uiso 1 1 calc R . .
C13 C 0.88324(19) 0.13069(13) 0.29476(18) 0.0249(5) Uani 1 1 d . . .
C14 C 0.8369(2) 0.09208(14) 0.53990(18) 0.0289(5) Uani 1 1 d . . .
H14 H 0.7698 0.0627 0.5001 0.035 Uiso 1 1 calc R . .
C15 C 0.9183(3) 0.04581(17) 0.6273(2) 0.0389(6) Uani 1 1 d . . .
H15A H 0.9485 0.0076 0.6001 0.058 Uiso 1 1 calc R . .
H15B H 0.8771 0.0257 0.6645 0.058 Uiso 1 1 calc R . .
H15C H 0.9805 0.0750 0.6721 0.058 Uiso 1 1 calc R . .
C16 C 0.7945(3) 0.15733(18) 0.5802(2) 0.0440(7) Uani 1 1 d . . .
H16A H 0.7518 0.1413 0.6185 0.066 Uiso 1 1 calc R . .
H16B H 0.7457 0.1863 0.5238 0.066 Uiso 1 1 calc R . .
H16C H 0.8592 0.1854 0.6235 0.066 Uiso 1 1 calc R . .
C17 C 0.8205(2) 0.12062(14) 0.18047(19) 0.0299(5) Uani 1 1 d . . .
H17 H 0.7512 0.0922 0.1687 0.036 Uiso 1 1 calc R . .
C18 C 0.7813(4) 0.19252(19) 0.1268(3) 0.0612(10) Uani 1 1 d . . .
H18A H 0.7366 0.2177 0.1568 0.092 Uiso 1 1 calc R . .
H18B H 0.7353 0.1844 0.0557 0.092 Uiso 1 1 calc R . .
H18C H 0.8475 0.2208 0.1340 0.092 Uiso 1 1 calc R . .
C19 C 0.8931(3) 0.0782(2) 0.1374(3) 0.0501(8) Uani 1 1 d . . .
H19A H 0.8501 0.0707 0.0656 0.075 Uiso 1 1 calc R . .
H19B H 0.9130 0.0325 0.1714 0.075 Uiso 1 1 calc R . .
H19C H 0.9620 0.1046 0.1480 0.075 Uiso 1 1 calc R . .
C20 C 0.41470(18) 0.10990(12) 0.22775(17) 0.0210(4) Uani 1 1 d . . .
C21 C 0.36559(19) 0.12356(13) 0.29687(18) 0.0249(5) Uani 1 1 d . . .
C22 C 0.2540(2) 0.15084(15) 0.2566(2) 0.0338(6) Uani 1 1 d . . .
H22 H 0.2177 0.1610 0.3001 0.041 Uiso 1 1 calc R . .
C23 C 0.1963(2) 0.16309(15) 0.1530(2) 0.0366(6) Uani 1 1 d . . .
H23 H 0.1223 0.1821 0.1279 0.044 Uiso 1 1 calc R . .
C24 C 0.2472(2) 0.14740(14) 0.0861(2) 0.0314(5) Uani 1 1 d . . .
H24 H 0.2067 0.1552 0.0166 0.038 Uiso 1 1 calc R . .
C25 C 0.35889(19) 0.11992(12) 0.12215(18) 0.0241(5) Uani 1 1 d . . .
C26 C 0.4291(2) 0.11072(14) 0.41115(19) 0.0302(5) Uani 1 1 d . . .
H26 H 0.5030 0.0881 0.4223 0.036 Uiso 1 1 calc R . .
C27 C 0.3631(3) 0.0588(2) 0.4503(2) 0.0476(7) Uani 1 1 d . . .
H27A H 0.4080 0.0484 0.5209 0.071 Uiso 1 1 calc R . .
H27B H 0.3481 0.0151 0.4115 0.071 Uiso 1 1 calc R . .
H27C H 0.2915 0.0804 0.4432 0.071 Uiso 1 1 calc R . .
C28 C 0.4550(3) 0.18135(19) 0.4709(2) 0.0500(8) Uani 1 1 d . . .
H28A H 0.4929 0.2138 0.4423 0.075 Uiso 1 1 calc R . .
H28B H 0.5040 0.1721 0.5410 0.075 Uiso 1 1 calc R . .
H28C H 0.3844 0.2025 0.4669 0.075 Uiso 1 1 calc R . .
C29 C 0.4160(2) 0.10361(14) 0.04989(18) 0.0295(5) Uani 1 1 d . . .
H29 H 0.4912 0.0820 0.0898 0.035 Uiso 1 1 calc R . .
C30 C 0.4362(3) 0.17295(17) 0.0029(3) 0.0465(7) Uani 1 1 d . . .
H30A H 0.3635 0.1935 -0.0405 0.070 Uiso 1 1 calc R . .
H30B H 0.4803 0.1627 -0.0365 0.070 Uiso 1 1 calc R . .
H30C H 0.4776 0.2064 0.0562 0.070 Uiso 1 1 calc R . .
C31 C 0.3465(3) 0.04965(17) -0.0320(2) 0.0439(7) Uani 1 1 d . . .
H31A H 0.3370 0.0061 -0.0001 0.066 Uiso 1 1 calc R . .
H31B H 0.3864 0.0392 -0.0749 0.066 Uiso 1 1 calc R . .
H31C H 0.2723 0.0696 -0.0725 0.066 Uiso 1 1 calc R . .
N1 N 0.71849(15) 0.08405(10) 0.32203(14) 0.0198(4) Uani 1 1 d . . .
N2 N 0.53199(15) 0.08391(10) 0.26689(14) 0.0200(4) Uani 1 1 d . . .
H1 H 0.627(2) 0.1772(18) 0.303(2) 0.027(7) Uiso 1 1 d . . .
Cl1 Cl 0.60357(6) 0.30105(3) 0.29722(5) 0.03553(19) Uani 1 1 d . . .
C32 C 0.1167(4) -0.1194(3) 0.1285(3) 0.0678(12) Uani 1 1 d . . .
H32A H 0.0656 -0.1322 0.0594 0.081 Uiso 1 1 calc R . .
H32B H 0.0791 -0.1320 0.1735 0.081 Uiso 1 1 calc R . .
Cl2 Cl 0.14460(10) -0.02615(6) 0.13590(8) 0.0700(3) Uani 1 1 d . . .
Cl3 Cl 0.24774(11) -0.16770(6) 0.16474(9) 0.0754(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0172(9) 0.0222(10) 0.0188(10) -0.0016(7) 0.0071(8) -0.0006(7)
C2 0.0203(10) 0.0226(10) 0.0209(10) 0.0007(8) 0.0090(8) 0.0002(8)
C3 0.0267(11) 0.0282(12) 0.0363(13) 0.0035(10) 0.0135(10) 0.0071(9)
C4 0.0411(15) 0.0251(12) 0.0481(16) 0.0044(11) 0.0179(13) 0.0081(10)
C5 0.0418(14) 0.0226(11) 0.0409(14) -0.0012(10) 0.0164(12) -0.0053(10)
C6 0.0260(11) 0.0266(11) 0.0334(12) -0.0008(9) 0.0102(10) -0.0051(9)
C7 0.0201(10) 0.0236(10) 0.0200(10) 0.0008(8) 0.0091(8) 0.0000(8)
C8 0.0149(9) 0.0222(10) 0.0274(11) -0.0017(8) 0.0074(8) 0.0000(7)
C9 0.0203(10) 0.0235(10) 0.0256(11) -0.0010(8) 0.0076(9) 0.0013(8)
C10 0.0198(10) 0.0303(12) 0.0288(11) -0.0047(9) 0.0037(9) -0.0001(9)
C11 0.0193(10) 0.0358(13) 0.0423(14) -0.0076(11) 0.0108(10) -0.0062(9)
C12 0.0239(11) 0.0377(13) 0.0398(14) -0.0047(11) 0.0184(10) -0.0068(10)
C13 0.0215(10) 0.0274(11) 0.0284(11) -0.0031(9) 0.0126(9) -0.0014(8)
C14 0.0251(11) 0.0379(13) 0.0225(11) 0.0001(9) 0.0083(9) -0.0016(9)
C15 0.0397(14) 0.0437(15) 0.0284(13) 0.0047(11) 0.0084(11) -0.0014(12)
C16 0.0423(15) 0.0571(19) 0.0394(15) -0.0008(13) 0.0234(13) 0.0105(13)
C17 0.0292(12) 0.0365(13) 0.0270(12) -0.0022(10) 0.0146(10) -0.0046(10)
C18 0.087(3) 0.0453(18) 0.0381(17) 0.0073(14) 0.0114(18) 0.0036(18)
C19 0.0425(16) 0.071(2) 0.0450(17) -0.0216(16) 0.0258(14) -0.0073(15)
C20 0.0147(9) 0.0213(10) 0.0253(10) 0.0012(8) 0.0061(8) 0.0005(7)
C21 0.0205(10) 0.0263(11) 0.0287(11) 0.0037(9) 0.0106(9) 0.0016(8)
C22 0.0236(11) 0.0417(14) 0.0406(14) 0.0040(11) 0.0176(10) 0.0065(10)
C23 0.0170(10) 0.0421(15) 0.0463(15) 0.0075(12) 0.0083(10) 0.0057(10)
C24 0.0218(11) 0.0341(13) 0.0313(12) 0.0055(10) 0.0032(9) -0.0007(9)
C25 0.0205(10) 0.0228(10) 0.0258(11) 0.0002(8) 0.0059(9) -0.0029(8)
C26 0.0272(11) 0.0386(13) 0.0279(12) 0.0049(10) 0.0143(10) 0.0075(10)
C27 0.0467(17) 0.060(2) 0.0414(16) 0.0134(14) 0.0229(14) -0.0021(15)
C28 0.0550(19) 0.0495(18) 0.0368(15) -0.0051(13) 0.0095(14) 0.0051(15)
C29 0.0286(11) 0.0347(13) 0.0238(11) -0.0006(9) 0.0089(9) 0.0001(10)
C30 0.0604(19) 0.0434(16) 0.0465(17) -0.0004(13) 0.0328(15) -0.0113(14)
C31 0.0534(18) 0.0414(15) 0.0348(14) -0.0095(12) 0.0154(13) -0.0077(13)
N1 0.0165(8) 0.0220(9) 0.0213(8) 0.0010(7) 0.0079(7) 0.0013(7)
N2 0.0163(8) 0.0223(9) 0.0212(8) -0.0001(7) 0.0074(7) 0.0004(7)
Cl1 0.0372(3) 0.0257(3) 0.0370(3) 0.0017(2) 0.0079(3) 0.0022(2)
C32 0.079(3) 0.083(3) 0.050(2) -0.0094(19) 0.035(2) -0.036(2)
Cl2 0.0863(7) 0.0691(6) 0.0700(6) -0.0050(5) 0.0476(6) -0.0032(5)
Cl3 0.0938(8) 0.0541(5) 0.0809(7) -0.0096(5) 0.0376(6) -0.0192(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.330(3) . ?
C1 N1 1.334(3) . ?
C1 H1 0.97(3) . ?
C2 C7 1.387(3) . ?
C2 C3 1.390(3) . ?
C2 N1 1.392(3) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9300 . ?
C7 N2 1.397(3) . ?
C8 C13 1.392(3) . ?
C8 C9 1.397(3) . ?
C8 N1 1.448(3) . ?
C9 C10 1.396(3) . ?
C9 C14 1.513(3) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(3) . ?
C12 H12 0.9300 . ?
C13 C17 1.515(3) . ?
C14 C15 1.527(4) . ?
C14 C16 1.531(4) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.519(4) . ?
C17 C18 1.522(4) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(3) . ?
C20 C25 1.400(3) . ?
C20 N2 1.447(3) . ?
C21 C22 1.393(3) . ?
C21 C26 1.523(3) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.396(3) . ?
C24 H24 0.9300 . ?
C25 C29 1.513(3) . ?
C26 C27 1.524(4) . ?
C26 C28 1.529(4) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.523(4) . ?
C29 C31 1.525(4) . ?
C29 H29 0.9800 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 Cl2 1.765(5) . ?
C32 Cl3 1.774(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 109.3(2) . . ?
N2 C1 H1 126.1(17) . . ?
N1 C1 H1 124.6(17) . . ?
C7 C2 C3 121.8(2) . . ?
C7 C2 N1 106.54(18) . . ?
C3 C2 N1 131.6(2) . . ?
C4 C3 C2 116.0(2) . . ?
C4 C3 H3 122.0 . . ?
C2 C3 H3 122.0 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 115.5(2) . . ?
C5 C6 H6 122.2 . . ?
C7 C6 H6 122.2 . . ?
C2 C7 C6 122.6(2) . . ?
C2 C7 N2 106.23(18) . . ?
C6 C7 N2 131.2(2) . . ?
C13 C8 C9 124.4(2) . . ?
C13 C8 N1 118.05(19) . . ?
C9 C8 N1 117.59(19) . . ?
C10 C9 C8 116.8(2) . . ?
C10 C9 C14 121.2(2) . . ?
C8 C9 C14 122.0(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 116.3(2) . . ?
C8 C13 C17 122.5(2) . . ?
C12 C13 C17 121.2(2) . . ?
C9 C14 C15 111.6(2) . . ?
C9 C14 C16 110.4(2) . . ?
C15 C14 C16 111.3(2) . . ?
C9 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C16 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C19 111.1(2) . . ?
C13 C17 C18 111.1(2) . . ?
C19 C17 C18 112.3(3) . . ?
C13 C17 H17 107.4 . . ?
C19 C17 H17 107.4 . . ?
C18 C17 H17 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 124.6(2) . . ?
C21 C20 N2 118.17(19) . . ?
C25 C20 N2 117.27(19) . . ?
C20 C21 C22 116.4(2) . . ?
C20 C21 C26 122.7(2) . . ?
C22 C21 C26 120.8(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 120.9(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 116.5(2) . . ?
C24 C25 C29 121.0(2) . . ?
C20 C25 C29 122.5(2) . . ?
C21 C26 C27 111.2(2) . . ?
C21 C26 C28 111.6(2) . . ?
C27 C26 C28 111.4(3) . . ?
C21 C26 H26 107.5 . . ?
C27 C26 H26 107.5 . . ?
C28 C26 H26 107.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 C30 110.1(2) . . ?
C25 C29 C31 111.6(2) . . ?
C30 C29 C31 111.5(2) . . ?
C25 C29 H29 107.8 . . ?
C30 C29 H29 107.8 . . ?
C31 C29 H29 107.8 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 N1 C2 108.92(18) . . ?
C1 N1 C8 124.39(19) . . ?
C2 N1 C8 126.65(18) . . ?
C1 N2 C7 109.02(18) . . ?
C1 N2 C20 125.11(19) . . ?
C7 N2 C20 125.66(18) . . ?
Cl2 C32 Cl3 109.7(2) . . ?
Cl2 C32 H32A 109.7 . . ?
Cl3 C32 H32A 109.7 . . ?
Cl2 C32 H32B 109.7 . . ?
Cl3 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 1.723
_refine_diff_density_min -0.835
_refine_diff_density_rms 0.086
#################################################################
_publ_section_exptl_refinement
;
The hydrogen atom H1 bound to C1 and in interaction with the counter-ion Cl1 was
freely refined. All other hydrogen positions were calculated after each cycle
of refinement using a riding model, with C---H = 0.93 \%A and U~iso~(H)
= 1.2U~eq~(C) for aromatic H atoms, with C---H = 0.98 \%A and
U~iso~(H) = 1.2U~eq~(C) for methine H atoms, with C---H = 0.97
\%A and U~iso~(H) = 1.2U~eq~(C) for methylene H atoms, and with
C---H = 0.96 \%A and U~iso~(H) = 1.5U~eq~(C) for methyl H atoms.
For a complete analysis of the crystal structure, see: platon_grec3005.txt
;
_publ_section_references
;
Agilent Technologies (2012). CrysAlis PRO. Yarnton, England.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887--897.
Farrugia, L. J. (1997). J. Appl. Cryst. 32, 565--?.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837--838.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P.,
Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.
39, 453--457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7--13.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920--925.
;
_publ_section_figure_captions
;
The molecular structure of the title compound (see grec3005_diamond.tif) with
displacement ellipsoids drawn at the 30% probability level (H-atoms are shown
as spheres of arbitrary size).
Selected crystal (colourless, 0.42 x 0.26 x 0.15 mm^3^).
;
#################################################################
_iucr_refine_instructions_details
;
TITL grec3005 in P2(1)/n
CELL 1.54180 12.6905 18.5911 14.3067 90.000 113.687 90.000
ZERR 4.00 0.0003 0.0003 0.0004 0.000 0.003 0.000
LATT 1
SYMM 1/2 - X, 1/2 + Y, 1/2 - Z
SFAC C H N CL
UNIT 128 164 8 12
MERG 2
OMIT 3 3 1
OMIT -8 3 6
FMAP 2
PLAN 25
ACTA 50.00
BOND $H
L.S. 8
WGHT 0.115400 3.672800
FVAR 2.94175
MOLE 1
C1 1 0.625306 0.125340 0.298382 11.00000 0.01719 0.02218 =
0.01881 -0.00158 0.00709 -0.00058
C2 1 0.684254 0.012402 0.304401 11.00000 0.02033 0.02262 =
0.02085 0.00074 0.00902 0.00022
C3 1 0.746605 -0.050555 0.313294 11.00000 0.02671 0.02824 =
0.03631 0.00354 0.01346 0.00707
AFIX 43
H3 2 0.826352 -0.050479 0.336297 11.00000 -1.20000
AFIX 0
C4 1 0.683008 -0.113328 0.285900 11.00000 0.04107 0.02509 =
0.04807 0.00441 0.01790 0.00814
AFIX 43
H4 2 0.721027 -0.156714 0.289795 11.00000 -1.20000
AFIX 0
C5 1 0.562815 -0.113487 0.252405 11.00000 0.04175 0.02258 =
0.04088 -0.00123 0.01638 -0.00534
AFIX 43
H5 2 0.523777 -0.157114 0.236044 11.00000 -1.20000
AFIX 0
C6 1 0.500638 -0.050971 0.242951 11.00000 0.02601 0.02657 =
0.03337 -0.00079 0.01018 -0.00510
AFIX 43
H6 2 0.420935 -0.050945 0.220374 11.00000 -1.20000
AFIX 0
C7 1 0.565297 0.012076 0.269501 11.00000 0.02011 0.02363 =
0.02004 0.00083 0.00907 -0.00002
C8 1 0.835515 0.110844 0.363172 11.00000 0.01492 0.02221 =
0.02743 -0.00175 0.00740 0.00000
C9 1 0.892460 0.115895 0.469202 11.00000 0.02028 0.02354 =
0.02558 -0.00100 0.00759 0.00134
C10 1 1.002859 0.145536 0.507332 11.00000 0.01981 0.03026 =
0.02877 -0.00468 0.00372 -0.00006
AFIX 43
H10 2 1.043634 0.150491 0.577424 11.00000 -1.20000
AFIX 0
C11 1 1.051987 0.167582 0.441545 11.00000 0.01929 0.03581 =
0.04226 -0.00760 0.01077 -0.00620
AFIX 43
H11 2 1.125136 0.187867 0.467973 11.00000 -1.20000
AFIX 0
C12 1 0.994030 0.159915 0.337234 11.00000 0.02388 0.03773 =
0.03977 -0.00474 0.01839 -0.00681
AFIX 43
H12 2 1.029252 0.174424 0.294545 11.00000 -1.20000
AFIX 0
C13 1 0.883236 0.130687 0.294756 11.00000 0.02146 0.02740 =
0.02841 -0.00313 0.01258 -0.00136
C14 1 0.836944 0.092085 0.539897 11.00000 0.02510 0.03793 =
0.02249 0.00010 0.00827 -0.00164
AFIX 13
H14 2 0.769759 0.062652 0.500112 11.00000 -1.20000
AFIX 0
C15 1 0.918308 0.045812 0.627274 11.00000 0.03968 0.04375 =
0.02837 0.00465 0.00844 -0.00143
AFIX 137
H15A 2 0.948507 0.007645 0.600076 11.00000 -1.50000
H15B 2 0.877061 0.025743 0.664536 11.00000 -1.50000
H15C 2 0.980506 0.074958 0.672143 11.00000 -1.50000
AFIX 0
C16 1 0.794470 0.157327 0.580196 11.00000 0.04231 0.05705 =
0.03942 -0.00076 0.02336 0.01052
AFIX 137
H16A 2 0.751831 0.141263 0.618547 11.00000 -1.50000
H16B 2 0.745716 0.186267 0.523836 11.00000 -1.50000
H16C 2 0.859231 0.185362 0.623475 11.00000 -1.50000
AFIX 0
C17 1 0.820453 0.120617 0.180470 11.00000 0.02917 0.03651 =
0.02702 -0.00224 0.01455 -0.00455
AFIX 13
H17 2 0.751221 0.092204 0.168689 11.00000 -1.20000
AFIX 0
C18 1 0.781347 0.192523 0.126794 11.00000 0.08691 0.04529 =
0.03811 0.00735 0.01135 0.00364
AFIX 137
H18A 2 0.736585 0.217657 0.156818 11.00000 -1.50000
H18B 2 0.735341 0.184431 0.055668 11.00000 -1.50000
H18C 2 0.847452 0.220831 0.134041 11.00000 -1.50000
AFIX 0
C19 1 0.893091 0.078194 0.137412 11.00000 0.04246 0.07068 =
0.04502 -0.02159 0.02581 -0.00728
AFIX 137
H19A 2 0.850138 0.070654 0.065633 11.00000 -1.50000
H19B 2 0.913042 0.032545 0.171378 11.00000 -1.50000
H19C 2 0.961998 0.104572 0.148016 11.00000 -1.50000
AFIX 0
C20 1 0.414703 0.109898 0.227748 11.00000 0.01470 0.02126 =
0.02529 0.00124 0.00610 0.00053
C21 1 0.365588 0.123559 0.296869 11.00000 0.02051 0.02632 =
0.02870 0.00372 0.01061 0.00161
C22 1 0.253988 0.150837 0.256620 11.00000 0.02357 0.04169 =
0.04063 0.00400 0.01760 0.00652
AFIX 43
H22 2 0.217667 0.160980 0.300081 11.00000 -1.20000
AFIX 0
C23 1 0.196296 0.163086 0.152950 11.00000 0.01702 0.04211 =
0.04634 0.00750 0.00830 0.00568
AFIX 43
H23 2 0.122305 0.182116 0.127881 11.00000 -1.20000
AFIX 0
C24 1 0.247221 0.147398 0.086130 11.00000 0.02181 0.03412 =
0.03125 0.00548 0.00323 -0.00068
AFIX 43
H24 2 0.206688 0.155229 0.016568 11.00000 -1.20000
AFIX 0
C25 1 0.358886 0.119924 0.122151 11.00000 0.02054 0.02282 =
0.02576 0.00024 0.00594 -0.00291
C26 1 0.429102 0.110721 0.411149 11.00000 0.02717 0.03865 =
0.02794 0.00487 0.01433 0.00748
AFIX 13
H26 2 0.502963 0.088138 0.422260 11.00000 -1.20000
AFIX 0
C27 1 0.363078 0.058828 0.450305 11.00000 0.04670 0.05977 =
0.04143 0.01341 0.02293 -0.00214
AFIX 137
H27A 2 0.408039 0.048351 0.520947 11.00000 -1.50000
H27B 2 0.348122 0.015085 0.411451 11.00000 -1.50000
H27C 2 0.291494 0.080369 0.443176 11.00000 -1.50000
AFIX 0
C28 1 0.455015 0.181346 0.470906 11.00000 0.05504 0.04950 =
0.03681 -0.00509 0.00955 0.00509
AFIX 137
H28A 2 0.492949 0.213796 0.442294 11.00000 -1.50000
H28B 2 0.504017 0.172055 0.541022 11.00000 -1.50000
H28C 2 0.384351 0.202535 0.466927 11.00000 -1.50000
AFIX 0
C29 1 0.416004 0.103609 0.049893 11.00000 0.02856 0.03468 =
0.02382 -0.00059 0.00887 0.00013
AFIX 13
H29 2 0.491245 0.082048 0.089809 11.00000 -1.20000
AFIX 0
C30 1 0.436231 0.172955 0.002922 11.00000 0.06037 0.04342 =
0.04650 -0.00036 0.03275 -0.01128
AFIX 137
H30A 2 0.363549 0.193455 -0.040508 11.00000 -1.50000
H30B 2 0.480314 0.162732 -0.036539 11.00000 -1.50000
H30C 2 0.477581 0.206401 0.056199 11.00000 -1.50000
AFIX 0
C31 1 0.346498 0.049651 -0.031970 11.00000 0.05337 0.04140 =
0.03477 -0.00945 0.01541 -0.00770
AFIX 137
H31A 2 0.337013 0.006138 -0.000051 11.00000 -1.50000
H31B 2 0.386405 0.039216 -0.074914 11.00000 -1.50000
H31C 2 0.272325 0.069635 -0.072473 11.00000 -1.50000
AFIX 0
N1 3 0.718485 0.084052 0.322032 11.00000 0.01654 0.02196 =
0.02129 0.00097 0.00787 0.00134
N2 3 0.531986 0.083906 0.266886 11.00000 0.01628 0.02234 =
0.02123 -0.00013 0.00736 0.00040
H1 2 0.626543 0.177186 0.302918 11.00000 0.02740
MOLE 2
CL1 4 0.603575 0.301053 0.297216 11.00000 0.03723 0.02570 =
0.03698 0.00167 0.00794 0.00220
MOLE 3
C32 1 0.116691 -0.119429 0.128546 11.00000 0.07880 0.08313 =
0.04972 -0.00936 0.03451 -0.03627
AFIX 23
H32A 2 0.065634 -0.132217 0.059354 11.00000 -1.20000
H32B 2 0.079116 -0.131993 0.173455 11.00000 -1.20000
AFIX 0
CL2 4 0.144599 -0.026153 0.135896 11.00000 0.08628 0.06910 =
0.07003 -0.00499 0.04764 -0.00322
CL3 4 0.247735 -0.167699 0.164745 11.00000 0.09378 0.05410 =
0.08088 -0.00956 0.03761 -0.01924
HKLF 4
REM grec3005 in P2(1)/n
REM R1 = 0.0777 for 6190 Fo > 4sig(Fo) and 0.0850 for all 7060 data
REM 346 parameters refined using 0 restraints
END
WGHT 0.1154 3.6747
REM Highest difference peak 1.723, deepest hole -0.835, 1-sigma level 0.086
Q1 1 0.6612 0.2996 0.3017 11.00000 0.05 1.72
Q2 1 0.6264 0.1986 0.6009 11.00000 0.05 1.52
Q3 1 0.4846 -0.1674 0.2390 11.00000 0.05 1.19
Q4 1 0.8830 0.0246 0.5369 11.00000 0.05 1.01
Q5 1 0.5789 -0.0263 0.2636 11.00000 0.05 0.95
Q6 1 0.0820 -0.0515 0.1116 11.00000 0.05 0.88
Q7 1 0.9772 0.1676 0.5662 11.00000 0.05 0.84
Q8 1 1.0153 0.0832 0.0799 11.00000 0.05 0.58
Q9 1 0.1018 0.1246 0.1004 11.00000 0.05 0.51
Q10 1 0.1730 -0.1724 0.1439 11.00000 0.05 0.50
Q11 1 0.2341 -0.0490 0.1643 11.00000 0.05 0.47
Q12 1 0.0519 0.0134 0.0997 11.00000 0.05 0.46
Q13 1 0.2010 0.0841 0.1334 11.00000 0.05 0.46
Q14 1 0.0432 -0.1094 0.1121 11.00000 0.05 0.45
Q15 1 0.6192 -0.1156 0.2783 11.00000 0.05 0.45
Q16 1 -0.0171 -0.0505 0.0858 11.00000 0.05 0.45
Q17 1 0.1836 -0.0393 0.2223 11.00000 0.05 0.44
Q18 1 0.1587 -0.1151 0.0663 11.00000 0.05 0.43
Q19 1 0.8436 0.1323 0.1040 11.00000 0.05 0.40
Q20 1 0.8979 0.1091 0.0398 11.00000 0.05 0.40
Q21 1 0.8933 0.1158 0.2153 11.00000 0.05 0.39
Q22 1 0.2992 0.1739 0.4017 11.00000 0.05 0.37
Q23 1 0.8562 0.1107 0.5214 11.00000 0.05 0.36
Q24 1 0.3200 0.1404 0.2794 11.00000 0.05 0.36
Q25 1 0.2694 -0.1441 0.0996 11.00000 0.05 0.34
;