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#$Date: 2022-11-07 07:13:41 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567763.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_1567763
loop_
_publ_author_name
'Zhao, Ruyan'
'Zhu, Tong'
'Wang, Sasa'
'Jarrett-Wilkins, Charlie'
'Najjarian, Amin Morteza'
'Lough, Alan J.'
'Hoogland, Sjoerd'
'Sargent, Edward H.'
'Seferos, Dwight S.'
_publ_section_title
;
 Engineering hydrogen bonding to align molecular dipoles in organic solids
 for efficient second harmonic generation
;
_journal_issue                   41
_journal_name_full               'Chemical Science'
_journal_page_first              12144
_journal_page_last               12148
_journal_paper_doi               10.1039/D2SC03994J
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 F N2 S, Br'
_chemical_formula_sum            'C12 H10 Br F N2 S'
_chemical_formula_weight         313.19
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-18 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                86.311(2)
_cell_angle_beta                 88.909(2)
_cell_angle_gamma                81.003(2)
_cell_formula_units_Z            1
_cell_length_a                   4.5926(3)
_cell_length_b                   5.6626(4)
_cell_length_c                   12.1650(8)
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.36
_cell_volume                     311.81(4)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4945
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_min         1.678
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    3.453
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       plate
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.371(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0228
_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)+(0.0035P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0332
_refine_ls_wR_factor_ref         0.0334
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.648
_reflns_Friedel_fraction_max     0.577
_reflns_number_gt                2181
_reflns_number_total             2260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03994j2.cif
_cod_data_source_block           d2132_b
_cod_depositor_comments
'Adding full bibliography for 1567763--1567764.cif.'
_cod_database_code               1567763
_shelx_shelxl_version_number     2018/3
_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_min   0.560
_shelx_estimated_absorpt_t_max   0.794
loop_
_space_group_symop_operation_xyz
'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 1.22605(3) 0.25929(3) 0.09750(3) 0.02393(10) Uani 1 1 d . . . . .
S1 S 0.64934(19) 0.42419(16) 0.37876(8) 0.0250(2) Uani 1 1 d . . . . .
F1 F -0.2306(5) 0.4054(4) 0.76952(19) 0.0331(8) Uani 0.836(5) 1 d . . P A 1
C9 C 0.2670(9) -0.1478(7) 0.7592(3) 0.0238(9) Uani 0.836(5) 1 d . . P A 1
H9A H 0.425453 -0.225795 0.717028 0.029 Uiso 0.836(5) 1 calc R U P A 1
C12 C -0.0930(8) 0.1799(6) 0.7942(3) 0.0236(8) Uani 0.836(5) 1 d . . P A 1
F1A F 0.503(3) -0.230(2) 0.7083(10) 0.035(4) Uiso 0.164(5) 1 d . . P A 2
C9A C 0.2670(9) -0.1478(7) 0.7592(3) 0.0238(9) Uani 0.164(5) 1 d . . P A 2
C12A C -0.0930(8) 0.1799(6) 0.7942(3) 0.0236(8) Uani 0.164(5) 1 d . . P A 2
H12A H -0.192760 0.337015 0.775762 0.028 Uiso 0.164(5) 1 calc R U P A 2
N1 N 0.6177(6) 0.7166(5) 0.1076(2) 0.0230(6) Uani 1 1 d . . . . .
H1C H 0.741515 0.728361 0.048862 0.035 Uiso 1 1 calc R U . . .
H1D H 0.454855 0.830068 0.098593 0.035 Uiso 1 1 calc R U . . .
H1E H 0.562901 0.568592 0.112485 0.035 Uiso 1 1 calc R U . . .
N2 N -0.0542(7) -0.1651(5) 0.9151(2) 0.0217(8) Uani 1 1 d . . . . .
C1 C 0.7722(7) 0.7540(6) 0.2109(2) 0.0221(7) Uani 1 1 d . . . . .
H1A H 0.964692 0.647106 0.214592 0.026 Uiso 1 1 calc R U . . .
H1B H 0.810290 0.921480 0.209261 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5932(8) 0.7036(6) 0.3110(3) 0.0190(8) Uani 1 1 d . . . . .
C3 C 0.3750(8) 0.8529(6) 0.3598(3) 0.0221(9) Uani 1 1 d . . . . .
H3A H 0.313081 1.014376 0.333688 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2494(9) 0.7441(7) 0.4530(3) 0.0259(9) Uani 1 1 d . . . . .
H4A H 0.095093 0.823854 0.496486 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3762(9) 0.5099(7) 0.4735(3) 0.0225(9) Uani 1 1 d . . . . .
C6 C 0.3007(9) 0.3503(7) 0.5605(3) 0.0233(9) Uani 1 1 d . . . . .
C7 C 0.2302(9) 0.2229(7) 0.6348(3) 0.0245(9) Uani 1 1 d . . . . .
C8 C 0.1334(9) 0.0864(7) 0.7277(3) 0.0206(9) Uani 1 1 d . . . . .
C10 C 0.1653(8) -0.2641(6) 0.8527(3) 0.0232(9) Uani 1 1 d . . . . .
H10A H 0.257535 -0.422628 0.872921 0.028 Uiso 1 1 calc R U . A 1
C11 C -0.1826(7) 0.0574(6) 0.8860(3) 0.0254(8) Uani 1 1 d . . . . .
H11A H -0.339278 0.132378 0.929989 0.031 Uiso 1 1 calc R U . A 1
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C2 S1 C5 91.60(19) . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
F1 C12 C8 118.6(3) . . ?
F1 C12 C11 118.4(3) . . ?
C8 C12 C11 123.0(3) . . ?
F1A C9A C10 122.8(6) . . ?
F1A C9A C8 117.2(6) . . ?
C10 C9A C8 119.3(4) . . ?
C8 C12A C11 123.0(3) . . ?
C8 C12A H12A 118.5 . . ?
C11 C12A H12A 118.5 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C10 N2 C11 117.9(3) . . ?
C2 C1 N1 111.5(2) . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 128.5(3) . . ?
C3 C2 S1 111.4(3) . . ?
C1 C2 S1 120.1(3) . . ?
C2 C3 C4 113.3(3) . . ?
C2 C3 H3A 123.3 . . ?
C4 C3 H3A 123.3 . . ?
C5 C4 C3 112.2(4) . . ?
C5 C4 H4A 123.9 . . ?
C3 C4 H4A 123.9 . . ?
C4 C5 C6 126.4(4) . . ?
C4 C5 S1 111.5(3) . . ?
C6 C5 S1 122.1(3) . . ?
C7 C6 C5 177.7(4) . . ?
C6 C7 C8 175.5(4) . . ?
C12 C8 C9 115.2(3) . . ?
C12A C8 C9A 115.2(3) . . ?
C12A C8 C7 121.6(4) . . ?
C12 C8 C7 121.6(4) . . ?
C9 C8 C7 123.2(4) . . ?
C9A C8 C7 123.2(4) . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 C9A 123.3(3) . . ?
N2 C10 H10A 118.4 . . ?
C9 C10 H10A 118.4 . . ?
N2 C11 C12 121.3(3) . . ?
N2 C11 C12A 121.3(3) . . ?
N2 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
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
S1 C2 1.721(4) . ?
S1 C5 1.722(4) . ?
F1 C12 1.351(4) . ?
C9 C10 1.387(5) . ?
C9 C8 1.404(5) . ?
C9 H9A 0.9500 . ?
C12 C8 1.366(5) . ?
C12 C11 1.368(5) . ?
F1A C9A 1.278(13) . ?
C9A C10 1.387(5) . ?
C9A C8 1.404(5) . ?
C12A C8 1.366(5) . ?
C12A C11 1.368(5) . ?
C12A H12A 0.9500 . ?
N1 C1 1.498(4) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N1 H1E 0.9100 . ?
N2 C10 1.325(5) . ?
N2 C11 1.334(4) . ?
C1 C2 1.494(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.359(5) . ?
C3 C4 1.413(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.421(5) . ?
C6 C7 1.192(4) . ?
C7 C8 1.431(5) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
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
_geom_hbond_publ_flag
N1 H1C N2 0.91 1.97 2.860(4) 165.2 1_664 yes
N1 H1D Br1 0.91 2.49 3.305(3) 149.0 1_465 yes
N1 H1E Br1 0.91 2.53 3.386(2) 157.1 1_455 yes
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
N1 C1 C2 C3 -85.0(4) . . . . ?
N1 C1 C2 S1 94.0(3) . . . . ?
C5 S1 C2 C3 0.0(3) . . . . ?
C5 S1 C2 C1 -179.2(3) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
S1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C3 C4 C5 S1 0.2(4) . . . . ?
C2 S1 C5 C4 -0.1(3) . . . . ?
C2 S1 C5 C6 179.9(3) . . . . ?
C11 C12A C8 C9A 0.9(5) . . . . ?
C11 C12A C8 C7 -177.2(3) . . . . ?
F1 C12 C8 C9 179.4(3) . . . . ?
C11 C12 C8 C9 0.9(5) . . . . ?
F1 C12 C8 C7 1.3(5) . . . . ?
C11 C12 C8 C7 -177.2(3) . . . . ?
C10 C9 C8 C12 -0.3(5) . . . . ?
C10 C9 C8 C7 177.8(4) . . . . ?
F1A C9A C8 C12A -171.0(7) . . . . ?
C10 C9A C8 C12A -0.3(5) . . . . ?
F1A C9A C8 C7 7.1(9) . . . . ?
C10 C9A C8 C7 177.8(4) . . . . ?
C11 N2 C10 C9 0.0(5) . . . . ?
C11 N2 C10 C9A 0.0(5) . . . . ?
C8 C9 C10 N2 -0.1(6) . . . . ?
F1A C9A C10 N2 170.0(7) . . . . ?
C8 C9A C10 N2 -0.1(6) . . . . ?
C10 N2 C11 C12 0.5(5) . . . . ?
C10 N2 C11 C12A 0.5(5) . . . . ?
F1 C12 C11 N2 -179.5(3) . . . . ?
C8 C12 C11 N2 -1.1(5) . . . . ?
C8 C12A C11 N2 -1.1(5) . . . . ?
