#------------------------------------------------------------------------------
#$Date: 2021-11-24 02:55:27 +0100 (Wed 24 de Nov de 2021) $
#$Revision: 270847 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/39/7243961.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243961
loop_
_publ_author_name
'Anderson, Trent E.'
'Culver, Evan W.'
'Badía-Domínguez, Irene'
'Wilcox, Wyatt D.'
'Buysse, Claire E.'
'Ruiz Delgado, M. Carmen'
'Rasmussen, Seth C.'
_publ_section_title
;
 Probing the nature of donor-acceptor effects in conjugated materials: a
 joint experimental and computational study of model conjugated oligomers.
;
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_paper_doi               10.1039/d1cp04603a
_journal_year                    2021
_chemical_formula_moiety         'C6 H3 Br N2 S'
_chemical_formula_sum            'C6 H3 Br N2 S'
_chemical_formula_weight         215.07
_chemical_melting_point          351
_chemical_name_common            4-Bromobenzo[c][1,2,5]thiadiazole
_chemical_name_systematic        4-Bromobenzo[c][1,2,5]thiadiazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-06-05 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                68.754(7)
_cell_angle_beta                 76.414(7)
_cell_angle_gamma                69.876(8)
_cell_formula_units_Z            2
_cell_length_a                   7.1075(10)
_cell_length_b                   7.1970(12)
_cell_length_c                   7.6350(10)
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.784
_cell_measurement_theta_min      6.275
_cell_volume                     339.06(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6734
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.672
_diffrn_reflns_theta_max         66.672
_diffrn_reflns_theta_min         6.269
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.415
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) 
was 0.1009 before and 0.0594 after correction. The Ratio of minimum to 
maximum transmission is 0.6594. The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0415P)²+0.5533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1150
_reflns_number_total             1192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cp04603a2.cif
_cod_data_source_block           cu_txa02_0m
_cod_database_code               7243961
_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.
;
_shelx_estimated_absorpt_t_max   0.555
_shelx_estimated_absorpt_t_min   0.241
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.17573(5) 0.14124(5) 0.88414(4) 0.02145(16) Uani 1 1 d . . . . .
S1 S 0.37972(12) 0.30669(13) 0.21422(11) 0.0199(2) Uani 1 1 d . . . . .
N1 N 0.3058(4) 0.2244(4) 0.4389(4) 0.0181(6) Uani 1 1 d . . . . .
N2 N 0.3593(4) 0.5465(4) 0.1856(4) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.2640(5) 0.3879(5) 0.5022(5) 0.0158(6) Uani 1 1 d . . . . .
C2 C 0.1999(5) 0.3906(5) 0.6932(5) 0.0165(6) Uani 1 1 d . . . . .
C3 C 0.1668(5) 0.5695(5) 0.7329(5) 0.0177(7) Uani 1 1 d . . . . .
H3 H 0.125832 0.571396 0.857347 0.021 Uiso 1 1 calc R . . . .
C4 C 0.1932(5) 0.7536(5) 0.5892(5) 0.0187(7) Uani 1 1 d . . . . .
H4 H 0.167146 0.873792 0.621226 0.022 Uiso 1 1 calc R . . . .
C5 C 0.2926(5) 0.5725(5) 0.3595(4) 0.0157(6) Uani 1 1 d . . . . .
C6 C 0.2562(5) 0.7577(5) 0.4046(5) 0.0194(7) Uani 1 1 d . . . . .
H6 H 0.274718 0.878354 0.311316 0.023 Uiso 1 1 calc R . . . .
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 S1 N1 101.33(14) . . ?
C1 N1 S1 105.5(2) . . ?
C5 N2 S1 106.0(2) . . ?
N1 C1 C2 126.7(3) . . ?
N1 C1 C5 114.4(3) . . ?
C5 C1 C2 118.9(3) . . ?
C1 C2 Br1 118.7(2) . . ?
C3 C2 Br1 122.2(3) . . ?
C3 C2 C1 119.0(3) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.3 . . ?
C6 C4 C3 121.4(3) . . ?
C6 C4 H4 119.3 . . ?
N2 C5 C1 112.8(3) . . ?
N2 C5 C6 126.3(3) . . ?
C6 C5 C1 121.0(3) . . ?
C4 C6 C5 118.1(3) . . ?
C4 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
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 C2 1.891(3) . ?
S1 N1 1.620(3) . ?
S1 N2 1.618(3) . ?
N1 C1 1.346(4) . ?
N2 C5 1.358(4) . ?
C1 C2 1.427(5) . ?
C1 C5 1.423(5) . ?
C2 C3 1.358(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.419(5) . ?
C4 H4 0.9300 . ?
C4 C6 1.367(5) . ?
C5 C6 1.420(5) . ?
C6 H6 0.9300 . ?
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 C2 C3 C4 177.5(2) . . . . ?
S1 N1 C1 C2 -177.7(3) . . . . ?
S1 N1 C1 C5 1.0(3) . . . . ?
S1 N2 C5 C1 -0.1(3) . . . . ?
S1 N2 C5 C6 178.7(3) . . . . ?
N1 S1 N2 C5 0.7(2) . . . . ?
N1 C1 C2 Br1 1.9(4) . . . . ?
N1 C1 C2 C3 179.1(3) . . . . ?
N1 C1 C5 N2 -0.6(4) . . . . ?
N1 C1 C5 C6 -179.5(3) . . . . ?
N2 S1 N1 C1 -1.0(2) . . . . ?
N2 C5 C6 C4 -178.6(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C5 C6 C4 0.1(5) . . . . ?
C2 C1 C5 N2 178.2(3) . . . . ?
C2 C1 C5 C6 -0.7(5) . . . . ?
C2 C3 C4 C6 -1.0(5) . . . . ?
C3 C4 C6 C5 0.7(5) . . . . ?
C5 C1 C2 Br1 -176.7(2) . . . . ?
C5 C1 C2 C3 0.4(5) . . . . ?
