#------------------------------------------------------------------------------
#$Date: 2022-10-04 22:59:10 +0300 (Tue, 04 Oct 2022) $
#$Revision: 278331 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567718.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_1567718
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         'C23 H18 Cl N3 O2'
_chemical_formula_sum            'C23 H18 Cl N3 O2'
_chemical_formula_weight         403.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-20 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7822(3)
_cell_length_b                   12.3852(6)
_cell_length_c                   27.1093(14)
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.8330
_cell_measurement_theta_min      3.9040
_cell_volume                     1941.40(17)
_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, Mercury, ORTEP'
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'w/ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            7005
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.942
_diffrn_reflns_theta_min         3.924
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.660
_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    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0667
_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)+(0.1039P)²+0.0585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1829
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3132
_reflns_number_total             3727
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cy01441f2.cif
_cod_data_source_block           RM2231b_a
_cod_database_code               1567718
_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   0.359
_shelx_estimated_absorpt_t_max   0.921
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.1680(7) 0.5729(3) 0.31635(14) 0.0615(10) Uani 1 1 d . . . . .
N1 N 0.3349(8) 0.6104(3) 0.39038(15) 0.0491(10) Uani 1 1 d . . . . .
H1 H 0.445217 0.590489 0.409623 0.059 Uiso 1 1 calc R U . . .
C1 C 0.3097(9) 0.5543(4) 0.34814(18) 0.0444(10) Uani 1 1 d . . . . .
Cl1 Cl -0.2200(3) 0.97324(12) 0.46776(7) 0.0766(5) Uani 1 1 d . . . . .
O2 O 0.6829(7) 0.4895(3) 0.41233(13) 0.0585(10) Uani 1 1 d . . . . .
N2 N 0.4717(7) 0.4683(3) 0.34112(14) 0.0434(9) Uani 1 1 d . . . . .
C2 C 0.6372(8) 0.4343(4) 0.37589(17) 0.0427(10) Uani 1 1 d . . . . .
N3 N 0.8595(8) 0.1629(3) 0.34771(17) 0.0511(10) Uani 1 1 d . . . . .
C3 C 0.7577(8) 0.3313(3) 0.36948(17) 0.0417(10) Uani 1 1 d . . . . .
C4 C 0.7084(9) 0.2434(4) 0.33925(19) 0.0493(11) Uani 1 1 d . . . . .
H4 H 0.588255 0.240739 0.316464 0.059 Uiso 1 1 calc R U . . .
C5 C 1.0141(9) 0.1944(4) 0.38392(18) 0.0457(11) Uani 1 1 d . . . . .
C6 C 0.9555(8) 0.2994(4) 0.39851(16) 0.0402(10) Uani 1 1 d . . . . .
C7 C 1.0903(9) 0.3490(4) 0.43483(19) 0.0478(11) Uani 1 1 d . . . . .
H7 H 1.055728 0.418444 0.445636 0.057 Uiso 1 1 calc R U . . .
C8 C 1.2761(10) 0.2931(4) 0.4544(2) 0.0559(13) Uani 1 1 d . . . . .
H8 H 1.368104 0.326030 0.478223 0.067 Uiso 1 1 calc R U . . .
C9 C 1.3277(11) 0.1884(5) 0.4392(2) 0.0613(14) Uani 1 1 d . . . . .
H9 H 1.450712 0.151981 0.453779 0.074 Uiso 1 1 calc R U . . .
C10 C 1.2010(11) 0.1379(4) 0.4032(2) 0.0565(13) Uani 1 1 d . . . . .
H10 H 1.238363 0.068909 0.392241 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2663(9) 0.3510(4) 0.28328(19) 0.0514(12) Uani 1 1 d . . . . .
H12 H 0.140958 0.348256 0.304745 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2646(10) 0.2909(5) 0.2406(2) 0.0586(13) Uani 1 1 d . . . . .
H13 H 0.137838 0.247756 0.233028 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4527(11) 0.2949(5) 0.2088(2) 0.0600(14) Uani 1 1 d . . . . .
H14 H 0.454763 0.251882 0.180654 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6360(11) 0.3624(5) 0.2188(2) 0.0615(15) Uani 1 1 d . . . . .
H15 H 0.759396 0.366569 0.196825 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6372(9) 0.4239(4) 0.26129(19) 0.0483(11) Uani 1 1 d . . . . .
H16 H 0.759185 0.470676 0.267843 0.058 Uiso 1 1 calc R U . . .
C17 C 0.4538(8) 0.4150(4) 0.29412(17) 0.0421(10) Uani 1 1 d . . . . .
C18 C 0.1995(8) 0.6982(4) 0.40627(17) 0.0420(10) Uani 1 1 d . . . . .
C19 C 0.2856(9) 0.7617(4) 0.44408(19) 0.0497(11) Uani 1 1 d . . . . .
H19 H 0.430392 0.745971 0.457189 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1614(10) 0.8482(4) 0.46289(19) 0.0518(12) Uani 1 1 d . . . . .
H20 H 0.222496 0.890884 0.487941 0.062 Uiso 1 1 calc R U . . .
C21 C -0.0544(10) 0.8696(4) 0.4437(2) 0.0509(12) Uani 1 1 d . . . . .
C22 C -0.1418(10) 0.8085(4) 0.4057(2) 0.0534(12) Uani 1 1 d . . . . .
H22 H -0.285964 0.825171 0.392505 0.064 Uiso 1 1 calc R U . . .
C23 C -0.0180(9) 0.7224(4) 0.3867(2) 0.0491(11) Uani 1 1 d . . . . .
H23 H -0.078934 0.681055 0.361243 0.059 Uiso 1 1 calc R U . . .
C24 C 0.8617(15) 0.0603(5) 0.3209(3) 0.080(2) Uani 1 1 d . . . . .
H24A H 0.767968 0.066493 0.291810 0.119 Uiso 1 1 calc R U . . .
H24B H 0.801029 0.004260 0.341669 0.119 Uiso 1 1 calc R U . . .
H24C H 1.017534 0.042845 0.311655 0.119 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C1 N1 C18 126.8(4) . . ?
C1 N1 H1 116.6 . . ?
C18 N1 H1 116.6 . . ?
O1 C1 N1 125.4(5) . . ?
O1 C1 N2 119.3(4) . . ?
N1 C1 N2 115.2(4) . . ?
C2 N2 C1 125.3(4) . . ?
C2 N2 C17 120.3(4) . . ?
C1 N2 C17 114.4(4) . . ?
O2 C2 N2 121.2(4) . . ?
O2 C2 C3 118.5(4) . . ?
N2 C2 C3 120.3(4) . . ?
C4 N3 C5 109.4(4) . . ?
C4 N3 C24 124.4(5) . . ?
C5 N3 C24 126.2(5) . . ?
C4 C3 C6 105.6(4) . . ?
C4 C3 C2 130.8(4) . . ?
C6 C3 C2 123.4(4) . . ?
N3 C4 C3 110.2(4) . . ?
N3 C4 H4 124.9 . . ?
C3 C4 H4 124.9 . . ?
N3 C5 C10 128.8(5) . . ?
N3 C5 C6 107.8(4) . . ?
C10 C5 C6 123.3(5) . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 C3 134.9(4) . . ?
C5 C6 C3 107.0(4) . . ?
C8 C7 C6 118.9(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 117.0(5) . . ?
C9 C10 H10 121.5 . . ?
C5 C10 H10 121.5 . . ?
C17 C12 C13 119.8(5) . . ?
C17 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.7(5) . . ?
C12 C17 N2 120.7(4) . . ?
C16 C17 N2 118.5(5) . . ?
C19 C18 C23 118.8(5) . . ?
C19 C18 N1 117.7(4) . . ?
C23 C18 N1 123.4(5) . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 Cl1 119.3(4) . . ?
C20 C21 Cl1 120.1(4) . . ?
C21 C22 C23 120.8(5) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 119.4(5) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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
O1 C1 1.211(6) . ?
N1 C1 1.347(6) . ?
N1 C18 1.408(6) . ?
N1 H1 0.8600 . ?
C1 N2 1.431(6) . ?
Cl1 C21 1.729(5) . ?
O2 C2 1.230(6) . ?
N2 C2 1.407(6) . ?
N2 C17 1.438(6) . ?
C2 C3 1.464(7) . ?
N3 C4 1.345(6) . ?
N3 C5 1.384(7) . ?
N3 C24 1.464(7) . ?
C3 C4 1.392(7) . ?
C3 C6 1.443(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.390(7) . ?
C5 C6 1.401(7) . ?
C6 C7 1.398(7) . ?
C7 C8 1.384(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C17 1.375(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(7) . ?
C16 H16 0.9300 . ?
C18 C19 1.385(7) . ?
C18 C23 1.397(7) . ?
C19 C20 1.387(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(8) . ?
C22 C23 1.382(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
