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#$Date: 2022-10-04 22:59:10 +0300 (Tue, 04 Oct 2022) $
#$Revision: 278331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567712.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_1567712
loop_
_publ_author_name
'Dasgupta, Ayan'
'Guerzoni, Michael G.'
'Alotaibi, Nusaybah'
'van Ingen, Yara'
'Farshadfar, Kaveh'
'Richards, Emma'
'Ariafard, Alireza'
'Melen, Rebecca L.'
_publ_section_title
;
 Chemo- and regio-selective amidation of indoles with isocyanates using
 borane Lewis acids
;
_journal_issue                   19
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              5982
_journal_page_last               5990
_journal_paper_doi               10.1039/D2CY01441F
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C8 H7 B Cl3 N'
_chemical_formula_sum            'C8 H7 B Cl3 N'
_chemical_formula_weight         234.31
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-30 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.906(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.121(2)
_cell_length_b                   6.9264(7)
_cell_length_c                   9.8879(13)
_cell_measurement_reflns_used    1123
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.3460
_cell_measurement_theta_min      4.1260
_cell_volume                     973.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'SHELXL, ORTEP, mercury'
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2544
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.680
_diffrn_reflns_theta_min         3.657
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0378
_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)+(0.0275P)²+0.6801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1018
_reflns_number_total             1257
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cy01441f2.cif
_cod_data_source_block           rm2217b_a
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               1567712
_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   0.603
_shelx_estimated_absorpt_t_max   0.882
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C3 C 0.8267(2) 0.500000 0.6896(3) 0.0203(6) Uani 1 2 d S T P . .
C4 C 0.7317(2) 0.500000 0.6753(3) 0.0184(6) Uani 1 2 d S T P . .
C5 C 0.6599(2) 0.500000 0.5443(3) 0.0225(6) Uani 1 2 d S T P . .
H5 H 0.595670 0.500000 0.537228 0.027 Uiso 1 2 calc R U P . .
C6 C 0.6865(2) 0.500000 0.4232(3) 0.0264(7) Uani 1 2 d S T P . .
H6 H 0.639438 0.500000 0.330542 0.032 Uiso 1 2 calc R U P . .
C8 C 0.8517(2) 0.500000 0.5674(3) 0.0262(7) Uani 1 2 d S T P . .
H8 H 0.915923 0.500000 0.574541 0.031 Uiso 1 2 calc R U P . .
C7 C 0.7811(2) 0.500000 0.4348(3) 0.0274(7) Uani 1 2 d S T P . .
H7 H 0.797223 0.500000 0.349977 0.033 Uiso 1 2 calc R U P . .
Cl1 Cl 0.56507(4) 0.72003(8) 0.76832(6) 0.03092(18) Uani 1 1 d . . . . .
N1 N 0.72512(16) 0.500000 0.8176(2) 0.0185(5) Uani 1 2 d S T P . .
C1 C 0.8086(2) 0.500000 0.9123(3) 0.0239(6) Uani 1 2 d S T P . .
H1 H 0.820950 0.500000 1.013119 0.029 Uiso 1 2 calc R U P . .
B1 B 0.6299(2) 0.500000 0.8490(4) 0.0217(7) Uani 1 2 d S T P . .
Cl2 Cl 0.65529(6) 0.500000 1.04463(8) 0.0329(2) Uani 1 2 d S T P . .
C2 C 0.8830(2) 0.500000 0.8460(3) 0.0246(7) Uani 1 2 d S T P . .
H2A H 0.923049 0.383463 0.873425 0.030 Uiso 0.5 1 calc R U P . .
H2B H 0.923049 0.616537 0.873426 0.030 Uiso 0.5 1 calc R U 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C8 C3 C4 119.3(3) . . ?
C8 C3 C2 132.7(3) . . ?
C4 C3 C2 108.0(2) . . ?
C5 C4 C3 123.3(3) . . ?
C5 C4 N1 128.6(3) . . ?
C3 C4 N1 108.1(2) . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C7 C8 C3 118.5(3) . . ?
C7 C8 H8 120.7 . . ?
C3 C8 H8 120.7 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C1 N1 C4 109.4(2) . . ?
C1 N1 B1 126.3(2) . . ?
C4 N1 B1 124.3(2) . . ?
N1 C1 C2 112.4(3) . . ?
N1 C1 H1 123.8 . . ?
C2 C1 H1 123.8 . . ?
N1 B1 Cl2 109.3(2) . . ?
N1 B1 Cl1 107.62(13) . . ?
Cl2 B1 Cl1 110.21(11) . . ?
N1 B1 Cl1 107.62(13) . 6_565 ?
Cl2 B1 Cl1 110.21(11) . 6_565 ?
Cl1 B1 Cl1 111.80(18) . 6_565 ?
C1 C2 C3 102.0(2) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C3 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?
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
C3 C8 1.383(4) . ?
C3 C4 1.396(4) . ?
C3 C2 1.490(4) . ?
C4 C5 1.378(4) . ?
C4 N1 1.443(3) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C8 C7 1.380(4) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
Cl1 B1 1.840(2) . ?
N1 C1 1.290(4) . ?
N1 B1 1.573(4) . ?
C1 C2 1.483(4) . ?
C1 H1 0.9500 . ?
B1 Cl2 1.840(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
