#------------------------------------------------------------------------------
#$Date: 2022-03-02 00:56:46 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129765.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_7129765
loop_
_publ_author_name
'Kundu, Gargi'
'Ajithkumar, V. S.'
'Raj, K. Vipin'
'Vanka, Kumar'
'Tothadi, Srinu'
'Sen, Sakya S.'
_publ_section_title
;
 Substitution at sp3 boron of a six-membered NHC·BH3: convenient
 access to a dihydroxyborenium cation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06816D
_journal_year                    2022
_chemical_formula_moiety         'Br, C28 H42 B N2 O2'
_chemical_formula_sum            'C28 H42 B Br N2 O2'
_chemical_formula_weight         529.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-22 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.517(10)
_cell_length_b                   20.453(9)
_cell_length_c                   8.264(3)
_cell_measurement_reflns_used    3491
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.15
_cell_measurement_theta_min      2.46
_cell_volume                     2792(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1945
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            64957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.466
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.499
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1302 before and 0.0977 after correction. The Ratio of minimum to maximum transmission is 0.8330. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0412
_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)+(0.0358P)²+4.5991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1755
_reflns_number_total             2527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06816d2.cif
_cod_data_source_block           mo_gk_bh2br_1_0m_a
_cod_database_code               7129765
_shelx_shelxl_version_number     2016/6
_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   0.915
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -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_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
Br01 Br 0.49688(3) 0.750000 0.04728(6) 0.02436(17) Uani 1 2 d S T P . .
N1 N 0.25090(16) 0.80635(13) 0.5527(3) 0.0148(6) Uani 1 1 d . . . . .
O2 O 0.4255(2) 0.750000 0.4113(5) 0.0257(9) Uani 1 2 d S T P . .
O3 O 0.3211(2) 0.750000 0.2076(4) 0.0234(9) Uani 1 2 d S T P . .
C1 C 0.0874(2) 0.91041(19) 0.3321(5) 0.0283(9) Uani 1 1 d . . . . .
H1A H 0.037236 0.889018 0.297570 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.093585 0.951982 0.274468 0.042 Uiso 1 1 calc GR . . . .
H1C H 0.085297 0.918650 0.448884 0.042 Uiso 1 1 calc GR . . . .
C2 C 0.1591(2) 0.86629(18) 0.2941(4) 0.0203(8) Uani 1 1 d . . . . .
H2A H 0.150239 0.823601 0.350367 0.024 Uiso 1 1 calc R . . . .
C3 C 0.2373(2) 0.89535(17) 0.3573(4) 0.0189(8) Uani 1 1 d . . . . .
C4 C 0.2806(2) 0.86715(16) 0.4848(4) 0.0151(7) Uani 1 1 d . . . . .
C5 C 0.2789(3) 0.750000 0.4983(6) 0.0159(11) Uani 1 2 d S T P . .
C6 C 0.1639(2) 0.8528(2) 0.1120(4) 0.0287(9) Uani 1 1 d . . . . .
H6A H 0.211685 0.826041 0.088870 0.043 Uiso 1 1 calc GR . . . .
H6B H 0.167917 0.894361 0.053392 0.043 Uiso 1 1 calc GR . . . .
H6C H 0.115063 0.829494 0.077241 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.1850(2) 0.81007(17) 0.6727(4) 0.0193(8) Uani 1 1 d . . . . .
H7A H 0.132235 0.813497 0.616494 0.023 Uiso 1 1 calc R . . . .
H7B H 0.192026 0.849504 0.740778 0.023 Uiso 1 1 calc R . . . .
C8 C 0.1859(3) 0.750000 0.7775(6) 0.0201(11) Uani 1 2 d S T P . .
H8A H 0.138042 0.750000 0.849494 0.024 Uiso 1 2 calc RS T P . .
H8B H 0.235139 0.750000 0.845944 0.024 Uiso 1 2 calc RS T P . .
C9 C 0.3508(2) 0.89487(17) 0.5499(4) 0.0186(8) Uani 1 1 d . . . . .
C10 C 0.3943(2) 0.86553(18) 0.6948(4) 0.0202(8) Uani 1 1 d . . . . .
H10 H 0.383169 0.817472 0.695056 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3630(2) 0.8933(2) 0.8544(5) 0.0313(10) Uani 1 1 d . . . . .
H11A H 0.388404 0.870062 0.944822 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.304160 0.887832 0.859870 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.376460 0.939920 0.860923 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.4858(2) 0.8746(3) 0.6868(5) 0.0453(12) Uani 1 1 d . . . . .
H12A H 0.511348 0.850259 0.775267 0.068 Uiso 1 1 calc GR . . . .
H12B H 0.498871 0.921127 0.697058 0.068 Uiso 1 1 calc GR . . . .
H12C H 0.505913 0.858175 0.582915 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.3785(2) 0.95224(18) 0.4783(4) 0.0219(8) Uani 1 1 d . . . . .
H13 H 0.426075 0.972538 0.518859 0.026 Uiso 1 1 calc R . . . .
C14 C 0.3382(2) 0.98017(18) 0.3497(4) 0.0248(9) Uani 1 1 d . . . . .
H14 H 0.359136 1.018724 0.301062 0.030 Uiso 1 1 calc R . . . .
C15 C 0.2681(2) 0.95278(18) 0.2912(4) 0.0225(8) Uani 1 1 d . . . . .
H15 H 0.240275 0.973335 0.204362 0.027 Uiso 1 1 calc R . . . .
B1 B 0.3481(3) 0.750000 0.3605(7) 0.0171(13) Uani 1 2 d S T P . .
H3 H 0.359(4) 0.750000 0.147(8) 0.06(2) Uiso 1 2 d S T P . .
H2 H 0.450(4) 0.750000 0.328(8) 0.06(2) Uiso 1 2 d S T P . .
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'
Br Br -0.2901 2.4595 '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'
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
C4 N1 C7 117.7(3) . . ?
C5 N1 C4 119.9(3) . . ?
C5 N1 C7 122.2(3) . . ?
B1 O2 H2 102(5) . . ?
B1 O3 H3 109(5) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 107.9 . . ?
C1 C2 C6 110.4(3) . . ?
C3 C2 C1 111.1(3) . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 C6 111.4(3) . . ?
C6 C2 H2A 107.9 . . ?
C4 C3 C2 122.3(3) . . ?
C15 C3 C2 120.5(3) . . ?
C15 C3 C4 117.2(3) . . ?
C3 C4 N1 118.2(3) . . ?
C3 C4 C9 123.1(3) . . ?
C9 C4 N1 118.6(3) . . ?
N1 C5 N1 121.5(4) . 7_575 ?
N1 C5 B1 119.2(2) . . ?
N1 C5 B1 119.2(2) 7_575 . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.7(3) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 C7 109.7(4) . 7_575 ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 7_575 . ?
C7 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 7_575 . ?
H8A C8 H8B 108.2 . . ?
C4 C9 C10 122.3(3) . . ?
C13 C9 C4 116.8(3) . . ?
C13 C9 C10 120.8(3) . . ?
C9 C10 H10 107.6 . . ?
C9 C10 C11 111.9(3) . . ?
C9 C10 C12 112.7(3) . . ?
C11 C10 H10 107.6 . . ?
C12 C10 H10 107.6 . . ?
C12 C10 C11 109.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13 119.4 . . ?
C14 C13 C9 121.3(3) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C3 C15 H15 119.6 . . ?
C14 C15 C3 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
O2 B1 C5 116.9(5) . . ?
O3 B1 O2 127.7(5) . . ?
O3 B1 C5 115.4(5) . . ?
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
N1 C4 1.449(4) . ?
N1 C5 1.321(4) . ?
N1 C7 1.475(4) . ?
O2 B1 1.344(7) . ?
O2 H2 0.80(7) . ?
O3 B1 1.341(7) . ?
O3 H3 0.80(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.522(5) . ?
C2 H2A 1.0000 . ?
C2 C3 1.515(5) . ?
C2 C6 1.532(5) . ?
C3 C4 1.398(5) . ?
C3 C15 1.392(5) . ?
C4 C9 1.399(5) . ?
C5 B1 1.614(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.503(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.520(5) . ?
C9 C13 1.391(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.526(5) . ?
C10 C12 1.523(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.377(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(5) . ?
C15 H15 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
_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 C4 C9 C10 -3.4(5) . . . . ?
N1 C4 C9 C13 178.2(3) . . . . ?
N1 C5 B1 O2 -90.4(4) 7_575 . . . ?
N1 C5 B1 O2 90.4(4) . . . . ?
N1 C5 B1 O3 89.6(4) 7_575 . . . ?
N1 C5 B1 O3 -89.6(4) . . . . ?
N1 C7 C8 C7 -52.9(5) . . . 7_575 ?
C1 C2 C3 C4 111.9(4) . . . . ?
C1 C2 C3 C15 -66.7(4) . . . . ?
C2 C3 C4 N1 3.0(5) . . . . ?
C2 C3 C4 C9 -176.9(3) . . . . ?
C2 C3 C15 C14 178.8(3) . . . . ?
C3 C4 C9 C10 176.4(3) . . . . ?
C3 C4 C9 C13 -1.9(5) . . . . ?
C4 N1 C5 N1 -177.2(3) . . . 7_575 ?
C4 N1 C5 B1 1.9(6) . . . . ?
C4 N1 C7 C8 -156.4(3) . . . . ?
C4 C3 C15 C14 0.1(5) . . . . ?
C4 C9 C10 C11 -90.2(4) . . . . ?
C4 C9 C10 C12 146.3(4) . . . . ?
C4 C9 C13 C14 0.1(5) . . . . ?
C5 N1 C4 C3 93.5(4) . . . . ?
C5 N1 C4 C9 -86.6(4) . . . . ?
C5 N1 C7 C8 28.4(5) . . . . ?
C6 C2 C3 C4 -124.5(4) . . . . ?
C6 C2 C3 C15 56.9(4) . . . . ?
C7 N1 C4 C3 -81.8(4) . . . . ?
C7 N1 C4 C9 98.1(4) . . . . ?
C7 N1 C5 N1 -2.2(7) . . . 7_575 ?
C7 N1 C5 B1 177.0(4) . . . . ?
C9 C13 C14 C15 1.7(6) . . . . ?
C10 C9 C13 C14 -178.2(3) . . . . ?
C13 C9 C10 C11 88.1(4) . . . . ?
C13 C9 C10 C12 -35.5(5) . . . . ?
C13 C14 C15 C3 -1.8(6) . . . . ?
C15 C3 C4 N1 -178.3(3) . . . . ?
C15 C3 C4 C9 1.8(5) . . . . ?
