data_s3430b
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
#------------------------------------------------------------------------------
_publ_requested_journal ' ENTER JOURNAL NAME HERE'
_publ_contact_author
;
Madeleine Helliwell
;
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_coeditor_name ?
_publ_contact_author_phone ' ENTER PHONE NUMBER '
_publ_contact_author_fax ' ENTER FAX NUMBER '
_publ_contact_author_email ' ENTER EMAIL ADDRESS '
loop_
_publ_author_name
_publ_author_address
' FIRST AUTHORS NAME '
;
FIRST AUTHORS ADDRESS
;
_publ_section_title
;
ENTER SECTION TITLE
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically with restraints.
H atoms bonded to C were included in calculated positions.
H2N was found by difference Fourier methods and refined isotropically.
The molecule shows a considerable amount of disorder over 2
sites with occupancies constrained to sum to 1.0.
The ORTEP was drawn using 30% probability ellipsoids.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C21 H27 Cl N2 O2'
_chemical_formula_sum
'C21 H27 Cl N2 O2'
_chemical_formula_weight 374.90
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'
'O' 'O' 0.0106 0.0060
'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 Orthorhombic
_symmetry_space_group_name_H-M Pbcn
_symmetry_space_group_name_Hall -P2n2ab
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 18.293(2)
_cell_length_b 22.343(3)
_cell_length_c 9.9739(13)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 4076.6(9)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 949
_cell_measurement_theta_min 2.50
_cell_measurement_theta_max 19.41
_exptl_crystal_description rod
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.222
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1600
_exptl_absorpt_coefficient_mu 0.204
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 27596
_diffrn_reflns_av_R_equivalents 0.0878
_diffrn_reflns_av_sigmaI/netI 0.0592
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 1.44
_diffrn_reflns_theta_max 25.03
_reflns_number_total 3613
_reflns_number_gt 1885
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.1195P)^2^+0.0000P] 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 3613
_refine_ls_number_parameters 332
_refine_ls_number_restraints 490
_refine_ls_R_factor_all 0.1360
_refine_ls_R_factor_gt 0.0717
_refine_ls_wR_factor_ref 0.2172
_refine_ls_wR_factor_gt 0.1855
_refine_ls_goodness_of_fit_ref 0.983
_refine_ls_restrained_S_all 0.945
_refine_ls_shift/su_max 0.001
_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
Cl1 Cl 0.6281(3) 0.63226(18) 0.2010(5) 0.1234(16) Uani 0.596(7) 1 d PU A 1
Cl1B Cl 0.5944(5) 0.6445(3) 0.2442(10) 0.148(3) Uani 0.404(7) 1 d PU A 2
O1 O 0.66618(13) 0.98498(9) 0.21470(19) 0.0591(7) Uani 1 1 d U . .
O2 O 0.5208(3) 1.2294(3) 0.0761(5) 0.0743(17) Uani 0.596(7) 1 d PU A 1
O2B O 0.4668(4) 1.2050(4) 0.0078(7) 0.069(2) Uani 0.404(7) 1 d PU A 2
N1 N 0.70340(15) 0.91649(12) 0.0601(2) 0.0553(7) Uani 1 1 d U . .
N2 N 0.64112(15) 1.00165(12) -0.0044(3) 0.0503(7) Uani 1 1 d U . .
H2N H 0.6468(16) 0.9929(14) -0.079(3) 0.051(10) Uiso 1 1 d . . .
C1 C 0.8512(5) 0.9770(4) 0.2939(9) 0.089(3) Uani 0.596(7) 1 d PDU A 1
H1A H 0.8842 0.9537 0.3509 0.134 Uiso 0.596(7) 1 calc PR A 1
H1B H 0.8015 0.9752 0.3304 0.134 Uiso 0.596(7) 1 calc PR A 1
H1C H 0.8675 1.0188 0.2914 0.134 Uiso 0.596(7) 1 calc PR A 1
C2 C 0.9287(5) 0.9592(5) 0.0901(12) 0.115(3) Uani 0.596(7) 1 d PDU A 1
H2A H 0.9460 0.9998 0.1098 0.173 Uiso 0.596(7) 1 calc PR A 1
H2B H 0.9272 0.9533 -0.0072 0.173 Uiso 0.596(7) 1 calc PR A 1
H2C H 0.9622 0.9301 0.1304 0.173 Uiso 0.596(7) 1 calc PR A 1
C3 C 0.8517(5) 0.9507(4) 0.1488(10) 0.087(2) Uani 0.596(7) 1 d PDU A 1
H3 H 0.8171 0.9750 0.0935 0.105 Uiso 0.596(7) 1 calc PR A 1
C1B C 0.8628(11) 0.9811(8) 0.199(2) 0.132(6) Uani 0.404(7) 1 d PDU A 2
H1D H 0.8722 0.9601 0.2831 0.199 Uiso 0.404(7) 1 calc PR A 2
H1E H 0.8143 0.9996 0.2016 0.199 Uiso 0.404(7) 1 calc PR A 2
H1F H 0.8999 1.0121 0.1853 0.199 Uiso 0.404(7) 1 calc PR A 2
C2B C 0.9425(8) 0.9249(8) 0.034(2) 0.132(6) Uani 0.404(7) 1 d PDU A 2
H2D H 0.9657 0.9627 0.0081 0.198 Uiso 0.404(7) 1 calc PR A 2
H2E H 0.9403 0.8983 -0.0441 0.198 Uiso 0.404(7) 1 calc PR A 2
H2F H 0.9711 0.9058 0.1051 0.198 Uiso 0.404(7) 1 calc PR A 2
C3B C 0.8660(8) 0.9370(6) 0.0839(18) 0.107(4) Uani 0.404(7) 1 d PDU A 2
H3B H 0.8365 0.9534 0.0079 0.128 Uiso 0.404(7) 1 calc PR A 2
C4 C 0.8271(2) 0.88372(19) 0.1392(4) 0.0811(11) Uani 1 1 d DU . .
H4 H 0.8391 0.8675 0.0484 0.097 Uiso 1 1 calc R A 1
C5 C 0.8675(2) 0.84750(19) 0.2476(4) 0.0855(12) Uani 1 1 d U A .
H5A H 0.8539 0.8625 0.3365 0.128 Uiso 1 1 calc R . .
H5B H 0.9204 0.8517 0.2350 0.128 Uiso 1 1 calc R . .
H5C H 0.8539 0.8052 0.2404 0.128 Uiso 1 1 calc R . .
C6 C 0.74459(18) 0.88207(15) 0.1615(3) 0.0560(9) Uani 1 1 d U A .
H6 H 0.7355 0.9023 0.2494 0.067 Uiso 1 1 calc R . .
C7 C 0.71455(18) 0.82006(14) 0.1745(3) 0.0520(8) Uani 1 1 d U . .
C8 C 0.6606(2) 0.80873(16) 0.2687(3) 0.0647(10) Uani 1 1 d U A .
H8 H 0.6438 0.8404 0.3243 0.078 Uiso 1 1 calc R . .
C9 C 0.6310(3) 0.7526(2) 0.2831(4) 0.0943(14) Uani 1 1 d U . .
H9 H 0.5944 0.7456 0.3488 0.113 Uiso 1 1 calc R A .
C10 C 0.6545(3) 0.7067(2) 0.2022(5) 0.1009(15) Uani 1 1 d U A .
C11 C 0.7076(3) 0.71607(18) 0.1113(5) 0.0907(13) Uani 1 1 d U . .
H11 H 0.7242 0.6839 0.0569 0.109 Uiso 1 1 calc R A .
C12 C 0.7376(2) 0.77145(16) 0.0971(4) 0.0707(10) Uani 1 1 d U A .
H12 H 0.7752 0.7772 0.0328 0.085 Uiso 1 1 calc R . .
C13 C 0.7041(2) 0.89604(15) -0.0786(3) 0.0599(9) Uani 1 1 d U . .
H13A H 0.6539 0.8947 -0.1129 0.090 Uiso 1 1 calc R . .
H13B H 0.7256 0.8559 -0.0830 0.090 Uiso 1 1 calc R . .
H13C H 0.7332 0.9237 -0.1330 0.090 Uiso 1 1 calc R . .
C14 C 0.67068(18) 0.96824(14) 0.0964(3) 0.0499(8) Uani 1 1 d U A .
C15 C 0.6087(4) 1.0585(2) 0.0211(8) 0.0427(17) Uani 0.596(7) 1 d PGU A 1
C16 C 0.6425(3) 1.1012(2) 0.1011(7) 0.0484(17) Uani 0.596(7) 1 d PGU A 1
H16 H 0.6872 1.0921 0.1449 0.058 Uiso 0.596(7) 1 calc PR A 1
C17 C 0.6108(3) 1.1573(2) 0.1170(5) 0.0518(17) Uani 0.596(7) 1 d PGU A 1
H17 H 0.6338 1.1866 0.1717 0.062 Uiso 0.596(7) 1 calc PR A 1
C18 C 0.5453(3) 1.1706(2) 0.0529(5) 0.0549(18) Uani 0.596(7) 1 d PGU A 1
C19 C 0.5115(3) 1.1279(2) -0.0272(6) 0.0576(18) Uani 0.596(7) 1 d PGU A 1
H19 H 0.4668 1.1370 -0.0710 0.069 Uiso 0.596(7) 1 calc PR A 1
C20 C 0.5432(4) 1.0718(2) -0.0431(7) 0.0499(17) Uani 0.596(7) 1 d PGU A 1
H20 H 0.5202 1.0425 -0.0978 0.060 Uiso 0.596(7) 1 calc PR A 1
C21 C 0.4580(5) 1.2463(5) 0.0042(13) 0.099(3) Uani 0.596(7) 1 d PU A 1
H21A H 0.4668 1.2409 -0.0920 0.149 Uiso 0.596(7) 1 calc PR A 1
H21B H 0.4469 1.2884 0.0225 0.149 Uiso 0.596(7) 1 calc PR A 1
H21C H 0.4167 1.2214 0.0320 0.149 Uiso 0.596(7) 1 calc PR A 1
C15B C 0.5968(6) 1.0533(4) 0.0000(13) 0.050(2) Uani 0.404(7) 1 d PGU A 2
C16B C 0.6134(5) 1.0988(4) 0.0901(10) 0.052(2) Uani 0.404(7) 1 d PGU A 2
H16B H 0.6545 1.0950 0.1478 0.062 Uiso 0.404(7) 1 calc PR A 2
C17B C 0.5700(5) 1.1497(3) 0.0957(7) 0.053(2) Uani 0.404(7) 1 d PGU A 2
H17B H 0.5813 1.1808 0.1573 0.063 Uiso 0.404(7) 1 calc PR A 2
C18B C 0.5099(5) 1.1552(3) 0.0113(8) 0.054(2) Uani 0.404(7) 1 d PGU A 2
C19B C 0.4932(4) 1.1097(4) -0.0788(8) 0.056(2) Uani 0.404(7) 1 d PGU A 2
H19B H 0.4522 1.1135 -0.1365 0.067 Uiso 0.404(7) 1 calc PR A 2
C20B C 0.5367(6) 1.0588(4) -0.0845(10) 0.054(2) Uani 0.404(7) 1 d PGU A 2
H20B H 0.5254 1.0277 -0.1460 0.065 Uiso 0.404(7) 1 calc PR A 2
C21B C 0.4857(10) 1.2566(6) 0.0858(11) 0.072(3) Uani 0.404(7) 1 d PU A 2
H21D H 0.4800 1.2474 0.1813 0.108 Uiso 0.404(7) 1 calc PR A 2
H21E H 0.4535 1.2899 0.0618 0.108 Uiso 0.404(7) 1 calc PR A 2
H21F H 0.5366 1.2677 0.0677 0.108 Uiso 0.404(7) 1 calc PR A 2
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
Cl1 0.171(4) 0.0590(17) 0.140(3) 0.0207(18) -0.036(3) -0.017(2)
Cl1B 0.154(5) 0.072(3) 0.219(7) 0.012(4) 0.022(4) -0.021(3)
O1 0.0929(17) 0.0592(14) 0.0253(11) 0.0010(10) 0.0055(11) 0.0038(12)
O2 0.087(4) 0.078(3) 0.058(3) -0.011(3) -0.007(3) 0.016(3)
O2B 0.069(4) 0.072(4) 0.066(4) -0.004(4) 0.006(3) 0.009(4)
N1 0.086(2) 0.0526(16) 0.0272(13) -0.0032(11) 0.0033(13) 0.0032(15)
N2 0.0699(18) 0.0563(16) 0.0246(14) -0.0023(13) 0.0072(13) -0.0037(14)
C1 0.100(6) 0.065(4) 0.103(6) -0.008(4) 0.006(5) -0.006(4)
C2 0.087(6) 0.134(9) 0.124(8) 0.002(6) 0.024(5) -0.033(6)
C3 0.086(5) 0.102(5) 0.074(6) 0.005(5) 0.021(5) -0.019(5)
C1B 0.124(11) 0.101(10) 0.171(15) -0.005(10) 0.017(11) -0.019(9)
C2B 0.086(8) 0.144(14) 0.166(16) 0.016(10) 0.024(8) -0.015(9)
C3B 0.091(7) 0.119(8) 0.111(9) 0.019(6) 0.012(7) -0.007(6)
C4 0.080(3) 0.094(3) 0.069(3) 0.000(2) 0.013(2) -0.005(2)
C5 0.074(3) 0.096(3) 0.086(3) -0.011(2) -0.009(2) 0.017(2)
C6 0.072(2) 0.062(2) 0.0344(16) -0.0035(15) -0.0001(16) 0.0012(17)
C7 0.067(2) 0.0556(19) 0.0339(16) -0.0068(14) -0.0081(16) 0.0086(16)
C8 0.087(3) 0.068(2) 0.0383(18) 0.0003(16) 0.0014(18) 0.000(2)
C9 0.126(4) 0.089(3) 0.069(3) 0.018(2) -0.003(2) -0.030(3)
C10 0.143(4) 0.062(3) 0.098(4) 0.017(2) -0.038(3) -0.022(3)
C11 0.123(4) 0.054(2) 0.096(3) -0.017(2) -0.034(3) 0.016(2)
C12 0.080(3) 0.070(2) 0.063(2) -0.0179(19) -0.0081(19) 0.013(2)
C13 0.085(3) 0.063(2) 0.0314(17) -0.0053(15) 0.0042(17) 0.0030(18)
C14 0.070(2) 0.0528(19) 0.0270(16) 0.0039(14) 0.0054(15) -0.0101(16)
C15 0.060(4) 0.057(3) 0.011(3) 0.004(3) 0.004(3) -0.004(3)
C16 0.064(5) 0.052(3) 0.029(3) 0.009(2) -0.010(3) -0.004(3)
C17 0.071(5) 0.055(3) 0.030(3) 0.002(2) -0.008(3) -0.010(3)
C18 0.064(4) 0.063(4) 0.037(3) -0.005(3) 0.005(3) 0.009(3)
C19 0.053(4) 0.075(4) 0.045(4) -0.004(3) -0.010(3) 0.003(3)
C20 0.055(4) 0.068(4) 0.027(4) -0.011(3) 0.000(3) -0.009(3)
C21 0.080(5) 0.100(7) 0.118(8) -0.026(7) -0.023(5) 0.026(5)
C15B 0.059(5) 0.060(5) 0.030(5) 0.002(4) 0.007(4) -0.012(4)
C16B 0.066(6) 0.063(5) 0.026(4) 0.003(4) -0.012(4) 0.001(4)
C17B 0.065(6) 0.059(5) 0.034(5) -0.008(4) -0.004(4) -0.009(5)
C18B 0.049(5) 0.059(5) 0.054(5) -0.002(4) -0.001(4) -0.009(4)
C19B 0.045(5) 0.081(5) 0.042(6) -0.006(4) -0.003(4) -0.018(4)
C20B 0.060(5) 0.071(5) 0.032(6) -0.005(4) 0.008(4) -0.010(4)
C21B 0.101(10) 0.076(7) 0.040(6) -0.011(5) 0.003(6) 0.036(7)
_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
Cl1 C10 1.732(6) . ?
Cl1B C10 1.821(9) . ?
O1 C14 1.241(3) . ?
O2 C18 1.406(7) . ?
O2 C21 1.405(12) . ?
O2B C18B 1.364(10) . ?
O2B C21B 1.433(16) . ?
N1 C14 1.351(4) . ?
N1 C13 1.457(4) . ?
N1 C6 1.477(4) . ?
N2 C14 1.364(4) . ?
N2 C15B 1.411(6) . ?
N2 C15 1.424(4) . ?
N2 H2N 0.78(3) . ?
C1 C3 1.562(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.539(11) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.566(9) . ?
C3 H3 1.0000 . ?
C1B C3B 1.509(16) . ?
C1B H1D 0.9800 . ?
C1B H1E 0.9800 . ?
C1B H1F 0.9800 . ?
C2B C3B 1.510(15) . ?
C2B H2D 0.9800 . ?
C2B H2E 0.9800 . ?
C2B H2F 0.9800 . ?
C3B C4 1.493(12) . ?
C3B H3B 1.0000 . ?
C4 C6 1.526(5) . ?
C4 C5 1.540(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.496(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.386(5) . ?
C7 C12 1.397(4) . ?
C8 C9 1.373(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.345(6) . ?
C11 C12 1.361(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15B C16B 1.3900 . ?
C15B C20B 1.3900 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
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
C18 O2 C21 115.4(8) . . ?
C18B O2B C21B 120.2(11) . . ?
C14 N1 C13 121.8(3) . . ?
C14 N1 C6 119.2(2) . . ?
C13 N1 C6 118.8(3) . . ?
C14 N2 C15B 130.8(6) . . ?
C14 N2 C15 121.5(4) . . ?
C15B N2 C15 13.1(5) . . ?
C14 N2 H2N 121(2) . . ?
C15B N2 H2N 108(2) . . ?
C15 N2 H2N 117(2) . . ?
C2 C3 C1 108.1(7) . . ?
C2 C3 C4 111.0(8) . . ?
C1 C3 C4 114.5(6) . . ?
C2 C3 H3 107.6 . . ?
C1 C3 H3 107.6 . . ?
C4 C3 H3 107.6 . . ?
C3B C1B H1D 109.5 . . ?
C3B C1B H1E 109.5 . . ?
H1D C1B H1E 109.5 . . ?
C3B C1B H1F 109.5 . . ?
H1D C1B H1F 109.5 . . ?
H1E C1B H1F 109.5 . . ?
C3B C2B H2D 109.5 . . ?
C3B C2B H2E 109.5 . . ?
H2D C2B H2E 109.5 . . ?
C3B C2B H2F 109.5 . . ?
H2D C2B H2F 109.5 . . ?
H2E C2B H2F 109.5 . . ?
C4 C3B C2B 114.9(12) . . ?
C4 C3B C1B 102.8(12) . . ?
C2B C3B C1B 113.7(14) . . ?
C4 C3B H3B 108.4 . . ?
C2B C3B H3B 108.4 . . ?
C1B C3B H3B 108.4 . . ?
C3B C4 C6 123.0(7) . . ?
C3B C4 C5 116.7(7) . . ?
C6 C4 C5 111.1(3) . . ?
C3B C4 C3 28.7(5) . . ?
C6 C4 C3 107.4(5) . . ?
C5 C4 C3 108.8(5) . . ?
C3B C4 H4 81.4 . . ?
C6 C4 H4 109.9 . . ?
C5 C4 H4 109.9 . . ?
C3 C4 H4 109.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 110.7(3) . . ?
N1 C6 C4 113.1(3) . . ?
C7 C6 C4 113.5(3) . . ?
N1 C6 H6 106.3 . . ?
C7 C6 H6 106.3 . . ?
C4 C6 H6 106.3 . . ?
C8 C7 C12 116.5(3) . . ?
C8 C7 C6 119.3(3) . . ?
C12 C7 C6 124.2(3) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 Cl1 110.2(5) . . ?
C9 C10 Cl1 129.3(5) . . ?
C11 C10 Cl1B 135.2(5) . . ?
C9 C10 Cl1B 104.2(5) . . ?
Cl1 C10 Cl1B 25.9(2) . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 121.9(4) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N1 122.8(3) . . ?
O1 C14 N2 120.6(3) . . ?
N1 C14 N2 116.6(3) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 N2 122.0(4) . . ?
C20 C15 N2 117.9(4) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 O2 113.5(4) . . ?
C19 C18 O2 126.5(4) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C16B C15B C20B 120.0 . . ?
C16B C15B N2 119.5(6) . . ?
C20B C15B N2 120.5(6) . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
O2B C18B C19B 117.0(6) . . ?
O2B C18B C17B 123.0(6) . . ?
C19B C18B C17B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C19B C20B C15B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C15B C20B H20B 120.0 . . ?
O2B C21B H21D 109.5 . . ?
O2B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
O2B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.78(3) 2.14(3) 2.855(3) 152(3) 7_575
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.324
_refine_diff_density_min -0.283
_refine_diff_density_rms 0.062