#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:03:40 +0300 (Wed, 05 May 2021) $
#$Revision: 264949 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157932.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_7157932
loop_
_publ_author_name
'Iqbal, S. A.'
'Yuan, K.'
'Cid, J.'
'Pahl, J.'
'Ingleson, M. J.'
_publ_section_title
;
 Controlling selectivity in N-heterocycle directed borylation of indoles.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2949
_journal_page_last               2958
_journal_paper_doi               10.1039/d1ob00018g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C13 H9 B Cl2 N2'
_chemical_formula_sum            'C13 H9 B Cl2 N2'
_chemical_formula_weight         274.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-12-17 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.203(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2198(4)
_cell_length_b                   8.3969(5)
_cell_length_c                   19.8689(9)
_cell_measurement_reflns_used    8155
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.433
_cell_measurement_theta_min      2.636
_cell_volume                     1195.02(11)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.637
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5813
_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 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.7791. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       rod
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0344
_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)+(0.0388P)²+0.4860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00018g2.cif
_cod_data_source_block           mo_mi20014_0m
_cod_depositor_comments
'Adding full bibliography for 7157931--7157932.cif.'
_cod_database_code               7157932
_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   0.961
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C7(H7), C13(H13), C11(H11), C4(H4), C2(H2), C6(H6), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
Cl1 Cl 0.38556(5) 0.16422(4) 0.36185(2) 0.02130(9) Uani 1 1 d . . . . .
Cl2 Cl 0.76215(5) 0.20628(4) 0.31198(2) 0.02034(9) Uani 1 1 d . . . . .
N2 N 0.59692(15) 0.44471(13) 0.38434(5) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.75082(15) 0.38054(13) 0.48535(5) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.67367(17) 0.50305(16) 0.44530(6) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.84348(17) 0.36549(16) 0.55110(6) 0.0144(2) Uani 1 1 d . . . . .
C10 C 0.66499(18) 0.66386(16) 0.46061(7) 0.0164(2) Uani 1 1 d . . . . .
H10 H 0.717743 0.704085 0.503456 0.020 Uiso 1 1 calc R . . . .
C12 C 0.50170(19) 0.70378(17) 0.34809(7) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.443415 0.773021 0.314001 0.022 Uiso 1 1 calc R . . . .
C3 C 0.87377(18) 0.20055(16) 0.56124(7) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.72382(18) 0.22955(16) 0.45443(7) 0.0156(2) Uani 1 1 d . . . . .
C7 C 0.90177(18) 0.47787(17) 0.60085(6) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.882208 0.588633 0.593225 0.021 Uiso 1 1 calc R . . . .
C13 C 0.51358(18) 0.54337(17) 0.33612(7) 0.0169(2) Uani 1 1 d . . . . .
H13 H 0.462572 0.501292 0.293403 0.020 Uiso 1 1 calc R . . . .
C11 C 0.57676(18) 0.76339(16) 0.41123(7) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.567066 0.873913 0.420397 0.022 Uiso 1 1 calc R . . . .
C4 C 0.96304(19) 0.14630(17) 0.62366(7) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.984129 0.035836 0.631610 0.023 Uiso 1 1 calc R . . . .
C2 C 0.79876(18) 0.11879(17) 0.49995(7) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.801243 0.007045 0.492638 0.021 Uiso 1 1 calc R . . . .
C6 C 0.98998(19) 0.42002(18) 0.66219(7) 0.0193(3) Uani 1 1 d . . . . .
H6 H 1.031102 0.493159 0.697399 0.023 Uiso 1 1 calc R . . . .
C5 C 1.01983(19) 0.25718(18) 0.67351(7) 0.0200(3) Uani 1 1 d . . . . .
H5 H 1.080166 0.222053 0.716164 0.024 Uiso 1 1 calc R . . . .
B1 B 0.6199(2) 0.25694(18) 0.38009(8) 0.0165(3) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
C9 N2 B1 111.82(10) . . ?
C13 N2 C9 120.48(12) . . ?
C13 N2 B1 127.70(11) . . ?
C9 N1 C8 136.11(11) . . ?
C9 N1 C1 113.35(11) . . ?
C8 N1 C1 110.46(11) . . ?
N2 C9 N1 109.66(11) . . ?
N2 C9 C10 121.46(12) . . ?
N1 C9 C10 128.87(12) . . ?
N1 C8 C3 105.63(11) . . ?
C7 C8 N1 131.99(12) . . ?
C7 C8 C3 122.38(12) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.54(12) . . ?
C11 C10 H10 121.2 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.83(13) . . ?
C11 C12 H12 120.6 . . ?
C8 C3 C2 108.13(11) . . ?
C4 C3 C8 119.41(12) . . ?
C4 C3 C2 132.46(13) . . ?
N1 C1 B1 107.35(11) . . ?
C2 C1 N1 107.63(11) . . ?
C2 C1 B1 145.02(12) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 C8 116.73(13) . . ?
C6 C7 H7 121.6 . . ?
N2 C13 C12 120.75(12) . . ?
N2 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C10 C11 C12 120.91(13) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.51(13) . . ?
C5 C4 H4 120.7 . . ?
C3 C2 H2 125.9 . . ?
C1 C2 C3 108.15(12) . . ?
C1 C2 H2 125.9 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C5 121.81(13) . . ?
C5 C6 H6 119.1 . . ?
C4 C5 C6 121.15(12) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
Cl2 B1 Cl1 109.70(8) . . ?
N2 B1 Cl1 109.13(9) . . ?
N2 B1 Cl2 109.81(10) . . ?
C1 B1 Cl1 115.70(10) . . ?
C1 B1 Cl2 114.02(10) . . ?
C1 B1 N2 97.74(10) . . ?
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
Cl1 B1 1.8566(15) . ?
Cl2 B1 1.8480(16) . ?
N2 C9 1.3585(16) . ?
N2 C13 1.3497(16) . ?
N2 B1 1.5888(19) . ?
N1 C9 1.3749(16) . ?
N1 C8 1.3969(16) . ?
N1 C1 1.4116(16) . ?
C9 C10 1.3873(18) . ?
C8 C3 1.4126(19) . ?
C8 C7 1.3929(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3821(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3723(19) . ?
C12 C11 1.3955(19) . ?
C3 C4 1.4003(18) . ?
C3 C2 1.4429(18) . ?
C1 C2 1.3613(18) . ?
C1 B1 1.5874(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.3902(18) . ?
C13 H13 0.9500 . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.398(2) . ?
C5 H5 0.9500 . ?
