#------------------------------------------------------------------------------
#$Date: 2022-06-30 00:54:51 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/03/7130304.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_7130304
loop_
_publ_author_name
'Lyu, Hairong'
'Xie, Zuowei'
_publ_section_title
;
 Transition Metal Catalyzed Selective B(3)-H or B(4)-H Amination of
 o-Carboranes via Dehydrogenative BH/NH Cross-Coupling
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02852B
_journal_year                    2022
_chemical_formula_sum            'C18 H27 B10 N O3 S'
_chemical_formula_weight         445.56
_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_block_doi                 10.5517/ccdc.csd.cc2bl717
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                112.5805(17)
_cell_angle_beta                 97.0506(17)
_cell_angle_gamma                96.4610(16)
_cell_formula_units_Z            2
_cell_length_a                   7.2450(4)
_cell_length_b                   13.3323(8)
_cell_length_c                   13.4099(8)
_cell_measurement_reflns_used    674
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1168.80(12)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4214
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.877
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.745618
_exptl_absorpt_correction_T_min  0.655045
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0467
_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)+(0.0586P)²+0.5865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3603
_reflns_number_total             4214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02852b2.cif
_cod_data_source_block           12c
_cod_database_code               7130304
_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   0.924
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2014/6
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
S1 S 0.71921(9) 0.38580(4) 0.45198(5) 0.03810(17) Uani 1 1 d . . . . .
N1 N 0.7874(3) 0.44844(14) 0.58405(14) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.8620 0.5110 0.6093 0.046 Uiso 1 1 calc R U . . .
O1 O 0.8101(3) 0.45444(14) 0.40567(14) 0.0492(4) Uani 1 1 d . . . . .
O2 O 0.5181(2) 0.35852(15) 0.42874(14) 0.0505(4) Uani 1 1 d . . . . .
O3 O 0.7519(3) 1.15001(15) 0.98939(18) 0.0687(6) Uani 1 1 d . . . . .
C1 C 0.6865(3) 0.50095(18) 0.78809(18) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.5076(3) 0.41258(18) 0.69863(19) 0.0396(5) Uani 1 1 d . . . . .
H2 H 0.4064 0.4414 0.6521 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7019(3) 0.61730(18) 0.80134(19) 0.0403(5) Uani 1 1 d . . . . .
H11A H 0.6905 0.6318 0.7385 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7307(4) 0.70078(19) 0.89720(19) 0.0429(6) Uani 1 1 d . . . . .
H12A H 0.7474 0.6833 0.9582 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7399(3) 0.81800(18) 0.92036(19) 0.0395(5) Uani 1 1 d . . . . .
C14 C 0.7261(4) 0.8585(2) 0.8392(2) 0.0507(6) Uani 1 1 d . . . . .
H14A H 0.7139 0.8101 0.7661 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7302(5) 0.9687(2) 0.8651(2) 0.0584(7) Uani 1 1 d . . . . .
H15A H 0.7203 0.9941 0.8093 0.070 Uiso 1 1 calc R U . . .
C16 C 0.7488(4) 1.0428(2) 0.9730(2) 0.0477(6) Uani 1 1 d . . . . .
C17 C 0.7628(4) 1.0046(2) 1.0545(2) 0.0526(6) Uani 1 1 d . . . . .
H17A H 0.7756 1.0533 1.1275 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7578(4) 0.8935(2) 1.0274(2) 0.0529(7) Uani 1 1 d . . . . .
H18A H 0.7667 0.8684 1.0834 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7684(5) 1.2290(2) 1.0981(3) 0.0694(9) Uani 1 1 d . . . . .
H19A H 0.7688 1.3008 1.0975 0.104 Uiso 1 1 calc R U . . .
H19B H 0.6636 1.2110 1.1291 0.104 Uiso 1 1 calc R U . . .
H19C H 0.8842 1.2289 1.1413 0.104 Uiso 1 1 calc R U . . .
C20 C 0.8110(3) 0.26189(18) 0.41234(18) 0.0370(5) Uani 1 1 d . . . . .
C21 C 1.0036(4) 0.2661(2) 0.4305(2) 0.0464(6) Uani 1 1 d . . . . .
H21A H 1.0855 0.3333 0.4576 0.056 Uiso 1 1 calc R U . . .
C22 C 1.0731(4) 0.1692(2) 0.4080(2) 0.0539(7) Uani 1 1 d . . . . .
H22A H 1.2030 0.1718 0.4201 0.065 Uiso 1 1 calc R U . . .
C23 C 0.9540(4) 0.0678(2) 0.3679(2) 0.0521(7) Uani 1 1 d . . . . .
C24 C 0.7637(4) 0.0663(2) 0.3485(2) 0.0579(7) Uani 1 1 d . . . . .
H24A H 0.6817 -0.0010 0.3200 0.070 Uiso 1 1 calc R U . . .
C25 C 0.6901(4) 0.1622(2) 0.3702(2) 0.0488(6) Uani 1 1 d . . . . .
H25A H 0.5603 0.1594 0.3565 0.059 Uiso 1 1 calc R U . . .
C26 C 1.0322(6) -0.0367(3) 0.3485(3) 0.0836(11) Uani 1 1 d . . . . .
H26A H 1.1676 -0.0197 0.3665 0.125 Uiso 1 1 calc R U . . .
H26B H 0.9850 -0.0707 0.3940 0.125 Uiso 1 1 calc R U . . .
H26C H 0.9938 -0.0865 0.2727 0.125 Uiso 1 1 calc R U . . .
B3 B 0.7304(4) 0.4054(2) 0.6629(2) 0.0347(6) Uani 1 1 d . . . . .
B4 B 0.8773(4) 0.4356(2) 0.7897(2) 0.0391(6) Uani 1 1 d . . . . .
H4 H 1.0246 0.4774 0.8066 0.047 Uiso 1 1 calc R U . . .
B5 B 0.7400(4) 0.4632(2) 0.8945(2) 0.0456(7) Uani 1 1 d . . . . .
H5 H 0.7987 0.5222 0.9792 0.055 Uiso 1 1 calc R U . . .
B6 B 0.5009(4) 0.4504(3) 0.8352(2) 0.0484(7) Uani 1 1 d . . . . .
H6 H 0.4030 0.5005 0.8798 0.058 Uiso 1 1 calc R U . . .
B7 B 0.5638(4) 0.2853(2) 0.6349(2) 0.0421(6) Uani 1 1 d . . . . .
H7 H 0.5035 0.2280 0.5498 0.051 Uiso 1 1 calc R U . . .
B8 B 0.8018(4) 0.2971(2) 0.6945(2) 0.0399(6) Uani 1 1 d . . . . .
H8 H 0.8990 0.2469 0.6493 0.048 Uiso 1 1 calc R U . . .
B9 B 0.8092(4) 0.3323(2) 0.8368(2) 0.0472(7) Uani 1 1 d . . . . .
H9 H 0.9120 0.3052 0.8842 0.057 Uiso 1 1 calc R U . . .
B10 B 0.5756(5) 0.3416(3) 0.8642(3) 0.0528(7) Uani 1 1 d . . . . .
H10 H 0.5262 0.3205 0.9292 0.063 Uiso 1 1 calc R U . . .
B11 B 0.4254(4) 0.3123(3) 0.7386(3) 0.0507(7) Uani 1 1 d . . . . .
H11 H 0.2767 0.2724 0.7202 0.061 Uiso 1 1 calc R U . . .
B12 B 0.6144(4) 0.2391(2) 0.7407(3) 0.0480(7) Uani 1 1 d . . . . .
H12 H 0.5900 0.1511 0.7253 0.058 Uiso 1 1 calc R U . . .
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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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'
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
O2 S1 O1 118.77(11) . . ?
O2 S1 N1 108.53(11) . . ?
O1 S1 N1 106.25(10) . . ?
O2 S1 C20 108.23(11) . . ?
O1 S1 C20 108.51(11) . . ?
N1 S1 C20 105.83(10) . . ?
B3 N1 S1 124.29(15) . . ?
C16 O3 C19 118.3(2) . . ?
C11 C1 C2 117.01(18) . . ?
C11 C1 B5 123.4(2) . . ?
C2 C1 B5 109.75(19) . . ?
C11 C1 B4 123.6(2) . . ?
C2 C1 B4 109.03(17) . . ?
B5 C1 B4 62.30(16) . . ?
C11 C1 B6 116.6(2) . . ?
C2 C1 B6 60.95(15) . . ?
B5 C1 B6 62.29(17) . . ?
B4 C1 B6 113.26(18) . . ?
C11 C1 B3 116.67(18) . . ?
C2 C1 B3 61.33(14) . . ?
B5 C1 B3 112.68(18) . . ?
B4 C1 B3 60.89(14) . . ?
B6 C1 B3 113.67(18) . . ?
C1 C2 B11 112.25(19) . . ?
C1 C2 B7 112.26(18) . . ?
B11 C2 B7 62.42(16) . . ?
C1 C2 B6 62.06(15) . . ?
B11 C2 B6 62.63(17) . . ?
B7 C2 B6 114.5(2) . . ?
C1 C2 B3 62.88(14) . . ?
B11 C2 B3 114.43(19) . . ?
B7 C2 B3 62.07(14) . . ?
B6 C2 B3 115.90(19) . . ?
C12 C11 C1 123.2(2) . . ?
C11 C12 C13 128.1(2) . . ?
C18 C13 C14 117.1(2) . . ?
C18 C13 C12 119.6(2) . . ?
C14 C13 C12 123.3(2) . . ?
C15 C14 C13 121.0(2) . . ?
C14 C15 C16 120.9(2) . . ?
O3 C16 C17 124.9(2) . . ?
O3 C16 C15 116.0(2) . . ?
C17 C16 C15 119.1(2) . . ?
C16 C17 C18 119.5(2) . . ?
C17 C18 C13 122.5(2) . . ?
C25 C20 C21 120.4(2) . . ?
C25 C20 S1 119.91(19) . . ?
C21 C20 S1 119.52(19) . . ?
C22 C21 C20 119.0(2) . . ?
C21 C22 C23 121.6(3) . . ?
C24 C23 C22 117.9(2) . . ?
C24 C23 C26 121.2(3) . . ?
C22 C23 C26 120.9(3) . . ?
C23 C24 C25 121.6(3) . . ?
C20 C25 C24 119.3(3) . . ?
N1 B3 C2 121.21(19) . . ?
N1 B3 B4 122.2(2) . . ?
C2 B3 B4 102.48(18) . . ?
N1 B3 B8 130.1(2) . . ?
C2 B3 B8 103.78(18) . . ?
B4 B3 B8 60.12(15) . . ?
N1 B3 C1 117.53(18) . . ?
C2 B3 C1 55.79(13) . . ?
B4 B3 C1 58.16(14) . . ?
B8 B3 C1 104.54(17) . . ?
N1 B3 B7 127.3(2) . . ?
C2 B3 B7 57.91(14) . . ?
B4 B3 B7 106.97(18) . . ?
B8 B3 B7 60.03(15) . . ?
C1 B3 B7 103.23(18) . . ?
C1 B4 B3 60.95(14) . . ?
C1 B4 B5 58.46(15) . . ?
B3 B4 B5 109.58(19) . . ?
C1 B4 B8 106.55(19) . . ?
B3 B4 B8 59.95(14) . . ?
B5 B4 B8 108.5(2) . . ?
C1 B4 B9 105.5(2) . . ?
B3 B4 B9 108.73(19) . . ?
B5 B4 B9 60.20(17) . . ?
B8 B4 B9 60.12(16) . . ?
C1 B5 B4 59.24(15) . . ?
C1 B5 B10 105.7(2) . . ?
B4 B5 B10 108.1(2) . . ?
C1 B5 B9 105.9(2) . . ?
B4 B5 B9 59.92(16) . . ?
B10 B5 B9 60.31(18) . . ?
C1 B5 B6 59.60(15) . . ?
B4 B5 B6 108.60(19) . . ?
B10 B5 B6 59.53(18) . . ?
B9 B5 B6 108.2(2) . . ?
C2 B6 C1 56.99(14) . . ?
C2 B6 B10 104.2(2) . . ?
C1 B6 B10 105.0(2) . . ?
C2 B6 B11 58.26(16) . . ?
C1 B6 B11 104.7(2) . . ?
B10 B6 B11 60.03(18) . . ?
C2 B6 B5 103.36(19) . . ?
C1 B6 B5 58.12(15) . . ?
B10 B6 B5 60.22(18) . . ?
B11 B6 B5 107.5(2) . . ?
C2 B7 B11 58.58(16) . . ?
C2 B7 B12 104.8(2) . . ?
B11 B7 B12 60.32(18) . . ?
C2 B7 B8 105.12(18) . . ?
B11 B7 B8 108.8(2) . . ?
B12 B7 B8 60.31(16) . . ?
C2 B7 B3 60.02(14) . . ?
B11 B7 B3 109.54(19) . . ?
B12 B7 B3 108.66(19) . . ?
B8 B7 B3 59.69(14) . . ?
B3 B8 B4 59.93(14) . . ?
B3 B8 B7 60.27(15) . . ?
B4 B8 B7 107.01(18) . . ?
B3 B8 B9 108.58(19) . . ?
B4 B8 B9 59.96(16) . . ?
B7 B8 B9 107.2(2) . . ?
B3 B8 B12 108.60(19) . . ?
B4 B8 B12 107.4(2) . . ?
B7 B8 B12 59.65(16) . . ?
B9 B8 B12 59.70(17) . . ?
B12 B9 B4 107.8(2) . . ?
B12 B9 B8 60.28(16) . . ?
B4 B9 B8 59.93(15) . . ?
B12 B9 B5 107.9(2) . . ?
B4 B9 B5 59.88(16) . . ?
B8 B9 B5 108.14(19) . . ?
B12 B9 B10 60.01(18) . . ?
B4 B9 B10 107.7(2) . . ?
B8 B9 B10 108.3(2) . . ?
B5 B9 B10 59.85(18) . . ?
B6 B10 B11 60.23(18) . . ?
B6 B10 B5 60.25(17) . . ?
B11 B10 B5 107.7(2) . . ?
B6 B10 B12 108.6(2) . . ?
B11 B10 B12 60.02(18) . . ?
B5 B10 B12 107.5(2) . . ?
B6 B10 B9 108.4(2) . . ?
B11 B10 B9 107.5(2) . . ?
B5 B10 B9 59.85(17) . . ?
B12 B10 B9 59.55(18) . . ?
C2 B11 B7 59.00(16) . . ?
C2 B11 B10 104.6(2) . . ?
B7 B11 B10 108.2(2) . . ?
C2 B11 B6 59.11(16) . . ?
B7 B11 B6 108.8(2) . . ?
B10 B11 B6 59.74(18) . . ?
C2 B11 B12 104.9(2) . . ?
B7 B11 B12 59.95(17) . . ?
B10 B11 B12 60.21(18) . . ?
B6 B11 B12 108.4(2) . . ?
B7 B12 B9 107.8(2) . . ?
B7 B12 B11 59.73(17) . . ?
B9 B12 B11 108.0(2) . . ?
B7 B12 B10 107.6(2) . . ?
B9 B12 B10 60.44(18) . . ?
B11 B12 B10 59.76(18) . . ?
B7 B12 B8 60.04(16) . . ?
B9 B12 B8 60.02(16) . . ?
B11 B12 B8 108.1(2) . . ?
B10 B12 B8 108.5(2) . . ?
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 O2 1.4260(19) . ?
S1 O1 1.4346(18) . ?
S1 N1 1.6232(18) . ?
S1 C20 1.764(2) . ?
N1 B3 1.462(3) . ?
O3 C16 1.357(3) . ?
O3 C19 1.413(4) . ?
C1 C11 1.482(3) . ?
C1 C2 1.642(3) . ?
C1 B5 1.703(3) . ?
C1 B4 1.717(3) . ?
C1 B6 1.730(4) . ?
C1 B3 1.767(3) . ?
C2 B11 1.696(4) . ?
C2 B7 1.704(3) . ?
C2 B6 1.711(4) . ?
C2 B3 1.742(3) . ?
C11 C12 1.311(3) . ?
C12 C13 1.464(3) . ?
C13 C18 1.381(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.371(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.369(4) . ?
C17 C18 1.379(4) . ?
C20 C25 1.376(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.377(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.367(4) . ?
C23 C26 1.506(4) . ?
C24 C25 1.382(4) . ?
B3 B4 1.766(4) . ?
B3 B8 1.766(3) . ?
B3 B7 1.777(4) . ?
B4 B5 1.769(4) . ?
B4 B8 1.769(4) . ?
B4 B9 1.770(4) . ?
B5 B10 1.775(4) . ?
B5 B9 1.775(4) . ?
B5 B6 1.775(4) . ?
B6 B10 1.762(4) . ?
B6 B11 1.771(4) . ?
B7 B11 1.762(4) . ?
B7 B12 1.766(4) . ?
B7 B8 1.773(4) . ?
B8 B9 1.773(4) . ?
B8 B12 1.777(4) . ?
B9 B12 1.767(4) . ?
B9 B10 1.783(5) . ?
B10 B11 1.768(5) . ?
B10 B12 1.776(4) . ?
B11 B12 1.772(4) . ?
