#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033364.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_4033364
loop_
_publ_author_name
'Zhang, Sutao'
'Han, Yuxi'
'He, Jianghua'
'Zhang, Yuetao'
_publ_section_title
;
 B(C₆F₅)₃-Catalyzed C3-Selective C-H
 Borylation of Indoles: Synthesis, Intermediates, and Reaction Mechanism.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1377
_journal_page_last               1386
_journal_paper_doi               10.1021/acs.joc.7b02886
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H11 B F N O2'
_chemical_formula_sum            'C15 H11 B F N O2'
_chemical_formula_weight         267.06
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5875(7)
_cell_length_b                   10.4080(14)
_cell_length_c                   20.927(3)
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.92
_cell_measurement_theta_min      2.19
_cell_volume                     1217.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXP-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9015
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.0076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                2293
_reflns_number_total             3032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02886_si_002.cif
_cod_data_source_block           4g
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033364.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4033364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.3290(4) 0.1155(2) 0.09910(11) 0.0248(5) Uani 1 1 d .
H1A H -0.2923 0.0991 0.0550 0.037 Uiso 1 1 calc R
H1B H -0.4928 0.1425 0.1028 0.037 Uiso 1 1 calc R
H1C H -0.3051 0.0386 0.1236 0.037 Uiso 1 1 calc R
C2 C 0.0189(4) 0.2668(2) 0.09203(10) 0.0178(5) Uani 1 1 d .
H2 H 0.0676 0.2432 0.0512 0.021 Uiso 1 1 calc R
C3 C 0.1316(4) 0.3580(2) 0.12926(9) 0.0164(4) Uani 1 1 d .
C4 C 0.0125(4) 0.4377(2) 0.24292(10) 0.0194(5) Uani 1 1 d .
H4 H 0.1335 0.4981 0.2483 0.023 Uiso 1 1 calc R
C5 C -0.1586(4) 0.4186(2) 0.28861(10) 0.0204(5) Uani 1 1 d .
C6 C -0.3428(4) 0.3283(2) 0.28445(10) 0.0218(5) Uani 1 1 d .
H6 H -0.4518 0.3187 0.3177 0.026 Uiso 1 1 calc R
C7 C -0.3602(4) 0.2535(2) 0.23011(10) 0.0193(5) Uani 1 1 d .
H7 H -0.4808 0.1926 0.2256 0.023 Uiso 1 1 calc R
C8 C -0.0028(3) 0.3622(2) 0.18776(10) 0.0150(4) Uani 1 1 d .
C9 C -0.1912(4) 0.27275(19) 0.18252(10) 0.0155(4) Uani 1 1 d .
C10 C 0.6471(4) 0.57596(19) 0.11108(9) 0.0155(4) Uani 1 1 d .
C11 C 0.8226(4) 0.66217(19) 0.12730(10) 0.0180(5) Uani 1 1 d .
H11 H 0.8326 0.6971 0.1681 0.022 Uiso 1 1 calc R
C12 C 0.9854(4) 0.6948(2) 0.07928(11) 0.0202(5) Uani 1 1 d .
H12 H 1.1068 0.7532 0.0883 0.024 Uiso 1 1 calc R
C13 C 0.9704(4) 0.6424(2) 0.01859(10) 0.0196(5) Uani 1 1 d .
H13 H 1.0809 0.6670 -0.0123 0.024 Uiso 1 1 calc R
C14 C 0.7932(4) 0.5535(2) 0.00283(10) 0.0190(5) Uani 1 1 d .
H14 H 0.7823 0.5177 -0.0378 0.023 Uiso 1 1 calc R
C15 C 0.6356(3) 0.52192(18) 0.05073(10) 0.0148(4) Uani 1 1 d .
B1 B 0.3450(4) 0.4386(2) 0.10967(11) 0.0162(5) Uani 1 1 d .
F1 F -0.1511(2) 0.49204(13) 0.34308(5) 0.0307(3) Uani 1 1 d .
N1 N -0.1735(3) 0.21584(17) 0.12307(8) 0.0174(4) Uani 1 1 d .
O1 O 0.4649(2) 0.52566(13) 0.14865(6) 0.0167(3) Uani 1 1 d .
O2 O 0.4488(2) 0.43410(13) 0.04836(7) 0.0173(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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
N1 C2 C3 111.01(19)
C2 C3 C8 105.28(18)
C2 C3 B1 126.01(19)
C8 C3 B1 128.66(18)
C5 C4 C8 116.94(19)
C4 C5 F1 118.58(19)
C4 C5 C6 124.7(2)
F1 C5 C6 116.68(18)
C7 C6 C5 118.8(2)
C6 C7 C9 117.5(2)
C4 C8 C9 118.72(19)
C4 C8 C3 133.52(19)
C9 C8 C3 107.67(18)
N1 C9 C7 129.33(19)
N1 C9 C8 107.43(18)
C7 C9 C8 123.2(2)
C11 C10 C15 121.66(19)
C11 C10 O1 129.08(18)
C15 C10 O1 109.23(18)
C10 C11 C12 116.5(2)
C13 C12 C11 121.6(2)
C12 C13 C14 121.4(2)
C15 C14 C13 116.2(2)
C14 C15 C10 122.58(19)
C14 C15 O2 127.84(18)
C10 C15 O2 109.58(17)
O1 B1 O2 110.96(19)
O1 B1 C3 125.56(18)
O2 B1 C3 123.49(19)
C2 N1 C9 108.61(17)
C2 N1 C1 126.06(18)
C9 N1 C1 125.30(18)
C10 O1 B1 105.46(16)
C15 O2 B1 104.76(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.448(3)
C2 N1 1.363(3)
C2 C3 1.380(3)
C3 C8 1.437(3)
C3 B1 1.515(3)
C4 C5 1.367(3)
C4 C8 1.399(3)
C5 F1 1.373(2)
C5 C6 1.396(3)
C6 C7 1.381(3)
C7 C9 1.387(3)
C8 C9 1.410(3)
C9 N1 1.382(3)
C10 C11 1.372(3)
C10 C15 1.384(3)
C10 O1 1.389(2)
C11 C12 1.397(3)
C12 C13 1.385(3)
C13 C14 1.394(3)
C14 C15 1.374(3)
C15 O2 1.388(2)
B1 O1 1.391(3)
B1 O2 1.409(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095897
