data_ms545
_audit_creation_date               2020-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C16 H10 Br N2'
_chemical_formula_sum              'C16 H10 Br N2'
_chemical_formula_weight           310.17
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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'
 'Br' 'Br' -0.6763 1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_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                     11.2118(7)
_cell_length_b                     6.2678(4)
_cell_length_c                     17.6195(11)
_cell_angle_alpha                  90
_cell_angle_beta                   100.350(2)
_cell_angle_gamma                  90
_cell_volume                       1218.03(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7650
_cell_measurement_temperature      112(2)
_cell_measurement_theta_max        66.97
_cell_measurement_theta_min        4.35
_shelx_estimated_absorpt_T_max     0.348
_shelx_estimated_absorpt_T_min     0.348
_exptl_absorpt_coefficient_mu      4.463
_exptl_absorpt_correction_T_max    0.3478
_exptl_absorpt_correction_T_min    0.3478
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS-2012/1, Bruker 2012'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              red
_exptl_crystal_colour_primary      red
_exptl_crystal_density_diffrn      1.691
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               620
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.3
_exptl_crystal_size_min            0.3
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0279
_diffrn_reflns_av_unetI/netI       0.0207
_diffrn_reflns_Laue_measured_fraction_full  0.970
_diffrn_reflns_Laue_measured_fraction_max  0.970
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -5
_diffrn_reflns_limit_l_max         20
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              9061
_diffrn_reflns_point_group_measured_fraction_full  0.970
_diffrn_reflns_point_group_measured_fraction_max  0.970
_diffrn_reflns_theta_full          66.977
_diffrn_reflns_theta_max           66.977
_diffrn_reflns_theta_min           4.347
_diffrn_ambient_temperature        112(2)
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.970
_diffrn_measured_fraction_theta_max  0.970
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2074
_reflns_number_total               2105
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT, (Bruker 2012)'
_computing_data_collection         'Bruker APEX2, (Bruker 2012)'
_computing_data_reduction          'Bruker SAINT, (Bruker 2012)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max           0.319
_refine_diff_density_min           -0.339
_refine_diff_density_rms           0.070
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.131
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       172
_refine_ls_number_reflns           2105
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0265
_refine_ls_R_factor_gt             0.0261
_refine_ls_restrained_S_all        1.131
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0260P)²+2.0678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0682
_refine_ls_wR_factor_ref           0.0684
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H22(0.5) H21(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N22(H22), N21(H21), C204(H204), C205(H205), C206(H206), C202(H202),
 C203(H203), C7(H7), C18(H18), C3(H3), C2(H2)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br 0.53196(2) -0.22899(4) -0.15082(2) 0.01824(11) Uani 1 1 d . . . . .
 N22 N 0.38268(17) 0.3220(3) -0.07892(11) 0.0135(4) Uani 1 1 d . . . . .
 H22 H 0.432500 0.394673 -0.044020 0.016 Uiso 0.5 1 calc R . P A 2
 N21 N 0.63720(18) 0.2855(3) -0.00785(12) 0.0136(4) Uani 1 1 d . . . . .
 H21 H 0.579153 0.379134 -0.006462 0.016 Uiso 0.5 1 calc R . P B 1
 C204 C 1.1685(2) 0.3773(4) 0.20342(14) 0.0199(5) Uani 1 1 d . . . . .
 H204 H 1.249990 0.360319 0.229177 0.024 Uiso 1 1 calc R . . . .
 C205 C 1.0772(2) 0.2575(4) 0.22553(15) 0.0195(5) Uani 1 1 d . . . . .
 H205 H 1.095813 0.158558 0.266825 0.023 Uiso 1 1 calc R . . . .
 C206 C 0.9585(2) 0.2812(4) 0.18757(15) 0.0180(5) Uani 1 1 d . . . . .
 H206 H 0.896264 0.197554 0.202917 0.022 Uiso 1 1 calc R . . . .
 C201 C 0.9293(2) 0.4261(4) 0.12729(13) 0.0145(5) Uani 1 1 d . . . . .
 C20 C 0.8001(2) 0.4500(4) 0.08679(13) 0.0142(5) Uani 1 1 d . . . . .
 C19 C 0.7362(2) 0.6255(4) 0.10775(13) 0.0136(5) Uani 1 1 d . . . . .
 C6 C 0.4104(2) 0.1365(4) -0.11395(13) 0.0139(5) Uani 1 1 d . . . . .
 C5 C 0.5233(2) 0.0371(4) -0.09952(13) 0.0145(5) Uani 1 1 d . . . . .
 C4 C 0.6293(2) 0.1030(4) -0.05143(13) 0.0141(5) Uani 1 1 d . . . . .
 C1 C 0.7533(2) 0.2933(4) 0.03312(13) 0.0140(5) Uani 1 1 d . . . . .
 C202 C 1.0216(2) 0.5471(4) 0.10570(15) 0.0210(5) Uani 1 1 d . . . . .
 H202 H 1.003115 0.647392 0.064848 0.025 Uiso 1 1 calc R . . . .
 C203 C 1.1409(2) 0.5224(5) 0.14355(15) 0.0231(6) Uani 1 1 d . . . . .
 H203 H 1.203494 0.605239 0.128284 0.028 Uiso 1 1 calc R . . . .
 C7 C 0.3051(2) 0.0712(4) -0.16727(13) 0.0156(5) Uani 1 1 d . . . . .
 H7 H 0.298638 -0.051132 -0.199585 0.019 Uiso 1 1 calc R . . . .
 C18 C 0.7841(2) 0.7844(4) 0.16344(14) 0.0157(5) Uani 1 1 d . . . . .
 H18 H 0.864028 0.788187 0.192562 0.019 Uiso 1 1 calc R . . . .
 C3 C 0.7456(2) -0.0058(4) -0.03876(13) 0.0160(5) Uani 1 1 d . . . . .
 H3 H 0.764773 -0.134392 -0.062484 0.019 Uiso 1 1 calc R . . . .
 C2 C 0.8210(2) 0.1113(4) 0.01317(13) 0.0160(5) Uani 1 1 d . . . . .
 H2 H 0.903568 0.080149 0.033120 0.019 Uiso 1 1 calc R . . . .


_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
 Br1 C5 1.908(2) . ?
 N22 H22 0.8800 . ?
 N22 C19 1.378(3) 3_665 ?
 N22 C6 1.378(3) . ?
 N21 H21 0.8800 . ?
 N21 C4 1.372(3) . ?
 N21 C1 1.371(3) . ?
 C204 H204 0.9500 . ?
 C204 C205 1.381(4) . ?
 C204 C203 1.385(4) . ?
 C205 H205 0.9500 . ?
 C205 C206 1.386(4) . ?
 C206 H206 0.9500 . ?
 C206 C201 1.391(3) . ?
 C201 C20 1.503(3) . ?
 C201 C202 1.390(3) . ?
 C20 C19 1.398(3) . ?
 C20 C1 1.399(3) . ?
 C19 C18 1.433(3) . ?
 C6 C5 1.393(3) . ?
 C6 C7 1.430(3) . ?
 C5 C4 1.393(3) . ?
 C4 C3 1.453(3) . ?
 C1 C2 1.448(3) . ?
 C202 H202 0.9500 . ?
 C202 C203 1.392(3) . ?
 C203 H203 0.9500 . ?
 C7 H7 0.9500 . ?
 C7 C18 1.359(3) 3_665 ?
 C18 H18 0.9500 . ?
 C3 H3 0.9500 . ?
 C3 C2 1.346(3) . ?
 C2 H2 0.9500 . ?

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
 C19 N22 H22 125.8 3_665 . ?
 C6 N22 H22 125.8 . . ?
 C6 N22 C19 108.49(19) . 3_665 ?
 C4 N21 H21 126.8 . . ?
 C1 N21 H21 126.8 . . ?
 C1 N21 C4 106.49(19) . . ?
 C205 C204 H204 120.1 . . ?
 C205 C204 C203 119.7(2) . . ?
 C203 C204 H204 120.1 . . ?
 C204 C205 H205 119.9 . . ?
 C204 C205 C206 120.1(2) . . ?
 C206 C205 H205 119.9 . . ?
 C205 C206 H206 119.6 . . ?
 C205 C206 C201 120.8(2) . . ?
 C201 C206 H206 119.6 . . ?
 C206 C201 C20 120.1(2) . . ?
 C202 C201 C206 118.8(2) . . ?
 C202 C201 C20 121.1(2) . . ?
 C19 C20 C201 116.7(2) . . ?
 C19 C20 C1 125.7(2) . . ?
 C1 C20 C201 117.6(2) . . ?
 N22 C19 C20 126.7(2) 3_665 . ?
 N22 C19 C18 107.7(2) 3_665 . ?
 C20 C19 C18 125.5(2) . . ?
 N22 C6 C5 124.5(2) . . ?
 N22 C6 C7 108.1(2) . . ?
 C5 C6 C7 127.4(2) . . ?
 C6 C5 Br1 115.24(17) . . ?
 C4 C5 Br1 115.92(17) . . ?
 C4 C5 C6 128.8(2) . . ?
 N21 C4 C5 123.4(2) . . ?
 N21 C4 C3 109.9(2) . . ?
 C5 C4 C3 126.8(2) . . ?
 N21 C1 C20 125.9(2) . . ?
 N21 C1 C2 109.5(2) . . ?
 C20 C1 C2 124.6(2) . . ?
 C201 C202 H202 119.8 . . ?
 C201 C202 C203 120.4(2) . . ?
 C203 C202 H202 119.8 . . ?
 C204 C203 C202 120.2(2) . . ?
 C204 C203 H203 119.9 . . ?
 C202 C203 H203 119.9 . . ?
 C6 C7 H7 126.1 . . ?
 C18 C7 C6 107.7(2) 3_665 . ?
 C18 C7 H7 126.1 3_665 . ?
 C19 C18 H18 126.0 . . ?
 C7 C18 C19 108.0(2) 3_665 . ?
 C7 C18 H18 126.0 3_665 . ?
 C4 C3 H3 126.7 . . ?
 C2 C3 C4 106.5(2) . . ?
 C2 C3 H3 126.7 . . ?
 C1 C2 H2 126.2 . . ?
 C3 C2 C1 107.6(2) . . ?
 C3 C2 H2 126.2 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C5 C4 N21 -177.15(17) . . . . ?
 Br1 C5 C4 C3 2.3(3) . . . . ?
 N22 C19 C18 C7 -0.2(3) 3_665 . . 3_665 ?
 N22 C6 C5 Br1 175.60(18) . . . . ?
 N22 C6 C5 C4 -2.6(4) . . . . ?
 N22 C6 C7 C18 -0.4(3) . . . 3_665 ?
 N21 C4 C3 C2 1.0(3) . . . . ?
 N21 C1 C2 C3 -0.6(3) . . . . ?
 C204 C205 C206 C201 -0.4(4) . . . . ?
 C205 C204 C203 C202 -0.1(4) . . . . ?
 C205 C206 C201 C20 -179.9(2) . . . . ?
 C205 C206 C201 C202 0.0(4) . . . . ?
 C206 C201 C20 C19 101.0(3) . . . . ?
 C206 C201 C20 C1 -77.4(3) . . . . ?
 C206 C201 C202 C203 0.4(4) . . . . ?
 C201 C20 C19 N22 -179.4(2) . . . 3_665 ?
 C201 C20 C19 C18 0.9(3) . . . . ?
 C201 C20 C1 N21 178.3(2) . . . . ?
 C201 C20 C1 C2 -0.8(3) . . . . ?
 C201 C202 C203 C204 -0.3(4) . . . . ?
 C20 C201 C202 C203 -179.7(2) . . . . ?
 C20 C19 C18 C7 179.6(2) . . . 3_665 ?
 C20 C1 C2 C3 178.6(2) . . . . ?
 C19 N22 C6 C5 179.3(2) 3_665 . . . ?
 C19 N22 C6 C7 0.5(3) 3_665 . . . ?
 C19 C20 C1 N21 0.0(4) . . . . ?
 C19 C20 C1 C2 -179.1(2) . . . . ?
 C6 C5 C4 N21 1.1(4) . . . . ?
 C6 C5 C4 C3 -179.4(2) . . . . ?
 C5 C6 C7 C18 -179.1(2) . . . 3_665 ?
 C5 C4 C3 C2 -178.6(2) . . . . ?
 C4 N21 C1 C20 -178.0(2) . . . . ?
 C4 N21 C1 C2 1.2(3) . . . . ?
 C4 C3 C2 C1 -0.2(3) . . . . ?
 C1 N21 C4 C5 178.2(2) . . . . ?
 C1 N21 C4 C3 -1.3(3) . . . . ?
 C1 C20 C19 N22 -1.1(4) . . . 3_665 ?
 C1 C20 C19 C18 179.2(2) . . . . ?
 C202 C201 C20 C19 -78.9(3) . . . . ?
 C202 C201 C20 C1 102.7(3) . . . . ?
 C203 C204 C205 C206 0.5(4) . . . . ?
 C7 C6 C5 Br1 -5.9(3) . . . . ?
 C7 C6 C5 C4 175.9(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_vrf_PLAT029_ms545
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.970 Why?  
RESPONSE: This is due to low quality data.
;
_vrf_PLAT911_ms545
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.597         65 Report
RESPONSE: The structure was collected to 97% resulting in the 
missing reflections.
;
