#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/52/4065223.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_4065223
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         'C9 H13 N4 S, Br'
_chemical_formula_sum            'C9 H13 Br N4 S'
_chemical_formula_weight         289.20
_chemical_name_common            ms_lhmcbv_0m
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.5350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.79770(10)
_cell_length_b                   11.2416(2)
_cell_length_c                   13.5580(2)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.39
_cell_volume                     1145.06(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18454
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0166
_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)+(0.0212P)²+0.5777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0426
_reflns_number_gt                2486
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200629j_si_002.cif
_cod_data_source_block           '[CS_(Me)H]Br'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4065223
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.405489(17) 0.654950(12) 0.153888(9) 0.01429(5) Uani 1 1 d .
S1 S 0.89360(5) 0.74739(3) 0.50937(3) 0.01785(8) Uani 1 1 d .
N1 N 0.76474(15) 0.52157(10) 0.47520(8) 0.0136(2) Uani 1 1 d .
N2 N 0.75746(14) 0.58929(10) 0.62323(8) 0.0129(2) Uani 1 1 d .
N3 N 0.96686(15) 0.63054(10) 0.78409(8) 0.0132(2) Uani 1 1 d .
N4 N 1.24895(15) 0.62777(10) 0.85752(8) 0.0127(2) Uani 1 1 d .
C1 C 0.80330(17) 0.61986(12) 0.53525(10) 0.0126(2) Uani 1 1 d .
C2 C 0.7862(2) 0.51382(14) 0.37183(10) 0.0196(3) Uani 1 1 d .
H2A H 0.6923 0.5600 0.3250 0.029 Uiso 1 1 calc R
H2B H 0.7779 0.4305 0.3499 0.029 Uiso 1 1 calc R
H2C H 0.9028 0.5457 0.3711 0.029 Uiso 1 1 calc R
C3 C 0.70080(18) 0.43078(13) 0.52476(10) 0.0165(3) Uani 1 1 d .
H3 H 0.6665 0.3535 0.4985 0.020 Uiso 1 1 calc R
C4 C 0.69626(17) 0.47245(12) 0.61704(10) 0.0161(3) Uani 1 1 d .
H4 H 0.6585 0.4302 0.6682 0.019 Uiso 1 1 calc R
C5 C 0.79440(18) 0.66235(13) 0.71384(10) 0.0160(3) Uani 1 1 d .
H5A H 0.6991 0.6516 0.7488 0.019 Uiso 1 1 calc R
H5B H 0.7959 0.7471 0.6943 0.019 Uiso 1 1 calc R
C6 C 1.12136(18) 0.68562(12) 0.79028(10) 0.0135(3) Uani 1 1 d .
H6 H 1.1370 0.7544 0.7529 0.016 Uiso 1 1 calc R
C7 C 1.43955(18) 0.65698(12) 0.88682(11) 0.0158(3) Uani 1 1 d .
H7A H 1.4611 0.7241 0.8456 0.024 Uiso 1 1 calc R
H7B H 1.5079 0.5878 0.8749 0.024 Uiso 1 1 calc R
H7C H 1.4769 0.6785 0.9595 0.024 Uiso 1 1 calc R
C8 C 1.17530(19) 0.53238(12) 0.89541(10) 0.0168(3) Uani 1 1 d .
H8 H 1.2373 0.4763 0.9445 0.020 Uiso 1 1 calc R
C9 C 0.99780(18) 0.53353(13) 0.84956(10) 0.0164(3) Uani 1 1 d .
H9 H 0.9118 0.4787 0.8602 0.020 Uiso 1 1 calc R
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
Br1 0.01507(8) 0.01539(8) 0.01252(7) 0.00031(5) 0.00390(5) -0.00112(5)
S1 0.01995(17) 0.01331(17) 0.02208(17) 0.00166(13) 0.00872(13) -0.00096(13)
N1 0.0146(5) 0.0142(6) 0.0116(5) -0.0002(4) 0.0028(4) 0.0016(4)
N2 0.0125(5) 0.0148(6) 0.0113(5) -0.0003(4) 0.0032(4) -0.0001(4)
N3 0.0147(5) 0.0144(5) 0.0106(5) -0.0015(4) 0.0035(4) 0.0017(4)
N4 0.0146(5) 0.0121(5) 0.0118(5) -0.0004(4) 0.0041(4) -0.0005(4)
C1 0.0106(6) 0.0142(6) 0.0126(6) 0.0013(5) 0.0022(5) 0.0033(5)
C2 0.0246(7) 0.0228(7) 0.0116(6) -0.0018(5) 0.0051(5) 0.0053(6)
C3 0.0166(6) 0.0128(6) 0.0182(6) 0.0012(5) 0.0014(5) -0.0011(5)
C4 0.0149(6) 0.0160(7) 0.0166(6) 0.0038(5) 0.0030(5) -0.0014(5)
C5 0.0139(6) 0.0210(7) 0.0128(6) -0.0032(5) 0.0029(5) 0.0034(5)
C6 0.0172(6) 0.0123(6) 0.0116(6) -0.0014(5) 0.0050(5) 0.0006(5)
C7 0.0128(6) 0.0175(7) 0.0165(6) 0.0000(5) 0.0033(5) -0.0004(5)
C8 0.0196(7) 0.0146(7) 0.0153(6) 0.0024(5) 0.0029(5) -0.0023(5)
C9 0.0187(7) 0.0169(7) 0.0138(6) 0.0017(5) 0.0045(5) -0.0024(5)
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 111.04(11)
C1 N1 C2 124.14(12)
C3 N1 C2 124.81(12)
C1 N2 C4 110.33(11)
C1 N2 C5 123.85(12)
C4 N2 C5 125.17(11)
C6 N3 C9 108.96(11)
C6 N3 C5 125.53(12)
C9 N3 C5 125.38(12)
C6 N4 C8 109.08(11)
C6 N4 C7 126.49(12)
C8 N4 C7 124.42(11)
N1 C1 N2 104.43(11)
N1 C1 S1 127.50(10)
N2 C1 S1 128.03(10)
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C4 C3 N1 107.28(12)
C4 C3 H3 126.4
N1 C3 H3 126.4
C3 C4 N2 106.89(12)
C3 C4 H4 126.6
N2 C4 H4 126.6
N2 C5 N3 110.69(11)
N2 C5 H5A 109.5
N3 C5 H5A 109.5
N2 C5 H5B 109.5
N3 C5 H5B 109.5
H5A C5 H5B 108.1
N4 C6 N3 108.27(12)
N4 C6 H6 125.9
N3 C6 H6 125.9
N4 C7 H7A 109.5
N4 C7 H7B 109.5
H7A C7 H7B 109.5
N4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 N4 107.30(12)
C9 C8 H8 126.3
N4 C8 H8 126.3
C8 C9 N3 106.38(12)
C8 C9 H9 126.8
N3 C9 H9 126.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6753(14)
N1 C1 1.3577(17)
N1 C3 1.3861(18)
N1 C2 1.4578(16)
N2 C1 1.3772(16)
N2 C4 1.3923(18)
N2 C5 1.4413(17)
N3 C6 1.3370(18)
N3 C9 1.3860(17)
N3 C5 1.4688(17)
N4 C6 1.3259(17)
N4 C8 1.3790(17)
N4 C7 1.4691(17)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C4 1.3452(19)
C3 H3 0.9500
C4 H4 0.9500
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.357(2)
C8 H8 0.9500
C9 H9 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 -1.47(14)
C2 N1 C1 N2 177.86(11)
C3 N1 C1 S1 176.43(10)
C2 N1 C1 S1 -4.24(19)
C4 N2 C1 N1 1.55(14)
C5 N2 C1 N1 172.72(11)
C4 N2 C1 S1 -176.34(10)
C5 N2 C1 S1 -5.16(19)
C1 N1 C3 C4 0.86(15)
C2 N1 C3 C4 -178.47(12)
N1 C3 C4 N2 0.14(15)
C1 N2 C4 C3 -1.07(15)
C5 N2 C4 C3 -172.11(12)
C1 N2 C5 N3 -91.52(15)
C4 N2 C5 N3 78.34(15)
C6 N3 C5 N2 96.27(15)
C9 N3 C5 N2 -78.95(16)
C8 N4 C6 N3 0.34(15)
C7 N4 C6 N3 179.15(11)
C9 N3 C6 N4 -0.34(15)
C5 N3 C6 N4 -176.22(11)
C6 N4 C8 C9 -0.21(15)
C7 N4 C8 C9 -179.05(12)
N4 C8 C9 N3 0.00(15)
C6 N3 C9 C8 0.21(15)
C5 N3 C9 C8 176.09(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139098389
