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#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/52/4065225.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_4065225
loop_
_publ_author_name
'Slivarichova, Miriam'
'Ahmad, Ruaa'
'Kuo, Yu-Ying'
'Nunn, Joshua'
'Haddow, Mairi F.'
'Othman, Hafiizah'
'Owen, Gareth R.'
_publ_section_title
;
 New Mixed-Donor Bidentate Ligands Based on N-Heterocyclic Carbene and
 Thione Donors
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4779
_journal_paper_doi               10.1021/om200629j
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C21 H21 N4 S, Br'
_chemical_formula_sum            'C21 H21 Br N4 S'
_chemical_formula_weight         441.39
_chemical_name_common            ms_lhbmz_0m
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.584(2)
_cell_angle_beta                 87.5330(10)
_cell_angle_gamma                73.5450(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8981(2)
_cell_length_b                   9.0283(3)
_cell_length_c                   16.5419(6)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.36
_cell_volume                     984.83(6)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16355
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.4537
_exptl_absorpt_correction_T_min  0.3696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.2331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                4107
_reflns_number_total             4453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200629j_si_002.cif
_cod_data_source_block           '[CS_(Bn)H]Br'
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4065225
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.75019(2) 0.663797(17) 0.533549(10) 0.01603(7) Uani 1 1 d .
S1 S 0.34991(7) 0.94289(5) 0.22536(3) 0.02019(11) Uani 1 1 d .
N1 N -0.0051(2) 0.86567(16) 0.22141(9) 0.0157(3) Uani 1 1 d .
N2 N 0.1868(2) 0.74271(16) 0.31914(8) 0.0149(3) Uani 1 1 d .
N3 N 0.2900(2) 0.77725(16) 0.45023(9) 0.0139(3) Uani 1 1 d .
N4 N 0.1854(2) 0.82222(16) 0.57284(9) 0.0151(3) Uani 1 1 d .
C1 C 0.1772(3) 0.84867(19) 0.25457(10) 0.0149(3) Uani 1 1 d .
C2 C -0.0816(3) 0.9627(2) 0.14792(11) 0.0198(4) Uani 1 1 d .
H2A H 0.0002 1.0359 0.1350 0.024 Uiso 1 1 calc R
H2B H -0.2231 1.0239 0.1578 0.024 Uiso 1 1 calc R
C3 C -0.1081(3) 0.7726(2) 0.26514(11) 0.0194(4) Uani 1 1 d .
H3 H -0.2384 0.7644 0.2540 0.023 Uiso 1 1 calc R
C4 C 0.0107(3) 0.6965(2) 0.32600(11) 0.0179(4) Uani 1 1 d .
H4 H -0.0198 0.6248 0.3661 0.021 Uiso 1 1 calc R
C5 C 0.3491(3) 0.6950(2) 0.37646(10) 0.0159(3) Uani 1 1 d .
H5A H 0.4720 0.7175 0.3520 0.019 Uiso 1 1 calc R
H5B H 0.3806 0.5820 0.3899 0.019 Uiso 1 1 calc R
C6 C 0.2247(2) 0.71646(19) 0.51843(10) 0.0138(3) Uani 1 1 d .
H6 H 0.2090 0.6151 0.5266 0.017 Uiso 1 1 calc R
C7 C 0.1064(3) 0.7993(2) 0.65543(11) 0.0195(4) Uani 1 1 d .
H7A H 0.0007 0.7450 0.6534 0.023 Uiso 1 1 calc R
H7B H 0.0429 0.9015 0.6771 0.023 Uiso 1 1 calc R
C8 C 0.2289(3) 0.9548(2) 0.53855(11) 0.0181(4) Uani 1 1 d .
H8 H 0.2153 1.0478 0.5643 0.022 Uiso 1 1 calc R
C9 C 0.2937(3) 0.92671(19) 0.46194(11) 0.0176(4) Uani 1 1 d .
H9 H 0.3342 0.9961 0.4232 0.021 Uiso 1 1 calc R
C10 C -0.0727(3) 0.8655(2) 0.07681(10) 0.0187(4) Uani 1 1 d .
C11 C -0.2484(3) 0.8511(2) 0.04460(11) 0.0245(4) Uani 1 1 d .
H11 H -0.3762 0.9037 0.0670 0.029 Uiso 1 1 calc R
C12 C -0.2381(3) 0.7596(2) -0.02048(12) 0.0294(5) Uani 1 1 d .
H12 H -0.3587 0.7509 -0.0428 0.035 Uiso 1 1 calc R
C13 C -0.0528(4) 0.6819(2) -0.05245(12) 0.0297(5) Uani 1 1 d .
H13 H -0.0458 0.6183 -0.0962 0.036 Uiso 1 1 calc R
C14 C 0.1236(3) 0.6961(2) -0.02099(12) 0.0276(4) Uani 1 1 d .
H14 H 0.2511 0.6432 -0.0436 0.033 Uiso 1 1 calc R
C15 C 0.1139(3) 0.7876(2) 0.04342(11) 0.0226(4) Uani 1 1 d .
H15 H 0.2350 0.7973 0.0649 0.027 Uiso 1 1 calc R
C16 C 0.2701(3) 0.7063(2) 0.71209(10) 0.0165(3) Uani 1 1 d .
C17 C 0.2479(3) 0.5733(2) 0.75530(11) 0.0236(4) Uani 1 1 d .
H17 H 0.1303 0.5407 0.7491 0.028 Uiso 1 1 calc R
C18 C 0.3979(3) 0.4881(2) 0.80759(12) 0.0282(5) Uani 1 1 d .
H18 H 0.3820 0.3976 0.8370 0.034 Uiso 1 1 calc R
C19 C 0.5698(3) 0.5341(2) 0.81710(11) 0.0258(4) Uani 1 1 d .
H19 H 0.6721 0.4751 0.8527 0.031 Uiso 1 1 calc R
C20 C 0.5922(3) 0.6669(2) 0.77439(11) 0.0243(4) Uani 1 1 d .
H20 H 0.7096 0.6995 0.7810 0.029 Uiso 1 1 calc R
C21 C 0.4434(3) 0.7520(2) 0.72218(11) 0.0209(4) Uani 1 1 d .
H21 H 0.4598 0.8425 0.6929 0.025 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 0.0033 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'
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
C1 N1 C3 110.37(14)
C1 N1 C2 125.50(15)
C3 N1 C2 124.08(15)
C1 N2 C4 110.42(14)
C1 N2 C5 125.02(14)
C4 N2 C5 124.37(14)
C6 N3 C9 109.05(15)
C6 N3 C5 124.07(14)
C9 N3 C5 126.87(14)
C6 N4 C8 109.00(15)
C6 N4 C7 124.21(15)
C8 N4 C7 126.78(15)
N1 C1 N2 104.92(14)
N1 C1 S1 127.66(13)
N2 C1 S1 127.36(13)
N1 C2 C10 111.21(14)
N1 C2 H2A 109.4
C10 C2 H2A 109.4
N1 C2 H2B 109.4
C10 C2 H2B 109.4
H2A C2 H2B 108.0
C4 C3 N1 107.39(16)
C4 C3 H3 126.3
N1 C3 H3 126.3
C3 C4 N2 106.89(15)
C3 C4 H4 126.6
N2 C4 H4 126.6
N2 C5 N3 109.97(14)
N2 C5 H5A 109.7
N3 C5 H5A 109.7
N2 C5 H5B 109.7
N3 C5 H5B 109.7
H5A C5 H5B 108.2
N4 C6 N3 108.05(15)
N4 C6 H6 126.0
N3 C6 H6 126.0
N4 C7 C16 112.29(14)
N4 C7 H7A 109.1
C16 C7 H7A 109.1
N4 C7 H7B 109.1
C16 C7 H7B 109.1
H7A C7 H7B 107.9
C9 C8 N4 107.02(15)
C9 C8 H8 126.5
N4 C8 H8 126.5
C8 C9 N3 106.87(15)
C8 C9 H9 126.6
N3 C9 H9 126.6
C11 C10 C15 119.30(17)
C11 C10 C2 120.83(17)
C15 C10 C2 119.87(17)
C10 C11 C12 120.28(19)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 119.9(2)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 120.29(19)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 120.0(2)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C10 120.26(19)
C14 C15 H15 119.9
C10 C15 H15 119.9
C21 C16 C17 119.05(17)
C21 C16 C7 120.95(16)
C17 C16 C7 120.00(17)
C18 C17 C16 119.99(18)
C18 C17 H17 120.0
C16 C17 H17 120.0
C19 C18 C17 120.59(18)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 119.63(18)
C18 C19 H19 120.2
C20 C19 H19 120.2
C21 C20 C19 120.01(19)
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C21 C16 120.73(17)
C20 C21 H21 119.6
C16 C21 H21 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6846(18)
N1 C1 1.358(2)
N1 C3 1.391(2)
N1 C2 1.467(2)
N2 C1 1.369(2)
N2 C4 1.389(2)
N2 C5 1.447(2)
N3 C6 1.333(2)
N3 C9 1.385(2)
N3 C5 1.460(2)
N4 C6 1.327(2)
N4 C8 1.389(2)
N4 C7 1.471(2)
C2 C10 1.510(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.343(3)
C3 H3 0.9500
C4 H4 0.9500
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6 0.9500
C7 C16 1.513(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.344(3)
C8 H8 0.9500
C9 H9 0.9500
C10 C11 1.388(3)
C10 C15 1.394(3)
C11 C12 1.394(3)
C11 H11 0.9500
C12 C13 1.377(3)
C12 H12 0.9500
C13 C14 1.386(3)
C13 H13 0.9500
C14 C15 1.385(3)
C14 H14 0.9500
C15 H15 0.9500
C16 C21 1.391(3)
C16 C17 1.392(3)
C17 C18 1.391(3)
C17 H17 0.9500
C18 C19 1.381(3)
C18 H18 0.9500
C19 C20 1.388(3)
C19 H19 0.9500
C20 C21 1.385(3)
C20 H20 0.9500
C21 H21 0.9500
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
C3 N1 C1 N2 0.49(19)
C2 N1 C1 N2 -177.07(15)
C3 N1 C1 S1 -177.09(14)
C2 N1 C1 S1 5.3(3)
C4 N2 C1 N1 -0.67(19)
C5 N2 C1 N1 -175.78(15)
C4 N2 C1 S1 176.93(13)
C5 N2 C1 S1 1.8(2)
C1 N1 C2 C10 105.04(19)
C3 N1 C2 C10 -72.2(2)
C1 N1 C3 C4 -0.1(2)
C2 N1 C3 C4 177.46(16)
N1 C3 C4 N2 -0.3(2)
C1 N2 C4 C3 0.6(2)
C5 N2 C4 C3 175.75(16)
C1 N2 C5 N3 99.52(18)
C4 N2 C5 N3 -74.9(2)
C6 N3 C5 N2 100.45(18)
C9 N3 C5 N2 -80.3(2)
C8 N4 C6 N3 -0.58(19)
C7 N4 C6 N3 178.79(15)
C9 N3 C6 N4 0.44(19)
C5 N3 C6 N4 179.77(15)
C6 N4 C7 C16 79.5(2)
C8 N4 C7 C16 -101.2(2)
C6 N4 C8 C9 0.50(19)
C7 N4 C8 C9 -178.86(16)
N4 C8 C9 N3 -0.22(19)
C6 N3 C9 C8 -0.13(19)
C5 N3 C9 C8 -179.44(16)
N1 C2 C10 C11 110.31(19)
N1 C2 C10 C15 -69.0(2)
C15 C10 C11 C12 0.0(3)
C2 C10 C11 C12 -179.29(17)
C10 C11 C12 C13 0.7(3)
C11 C12 C13 C14 -1.0(3)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C10 0.0(3)
C11 C10 C15 C14 -0.3(3)
C2 C10 C15 C14 178.95(16)
N4 C7 C16 C21 54.8(2)
N4 C7 C16 C17 -125.43(18)
C21 C16 C17 C18 0.0(3)
C7 C16 C17 C18 -179.77(17)
C16 C17 C18 C19 -0.1(3)
C17 C18 C19 C20 0.4(3)
C18 C19 C20 C21 -0.5(3)
C19 C20 C21 C16 0.3(3)
C17 C16 C21 C20 0.0(3)
C7 C16 C21 C20 179.68(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139098391
