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#$Date: 2025-03-04 20:40:17 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298054 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134044.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_7134044
loop_
_publ_author_name
'Chakrabortty, Gopal'
'Pratim Sen, Partha'
'Raha Roy, Sudipta'
_publ_section_title
;
 Cobalt catalysed cross-dehydrogenative coupling of indoles: a
 photoinduced ligand to metal charge transfer process.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1898
_journal_page_last               1901
_journal_paper_doi               10.1039/d4cc05192k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C2.71 H2.12 N0.24 O0.12'
_chemical_formula_weight         39.81
_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   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-09-30 deposited with the CCDC.	2024-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.060(2)
_cell_angle_gamma                90
_cell_formula_units_Z            34
_cell_length_a                   14.0903(8)
_cell_length_b                   10.8057(6)
_cell_length_c                   11.6002(6)
_cell_measurement_reflns_used    6187
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.58
_cell_volume                     1720.51(16)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            42311
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.840
_diffrn_reflns_theta_max         24.840
_diffrn_reflns_theta_min         2.399
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0394
_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)+(0.0430P)²+0.6364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2434
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05192k2.cif
_cod_data_source_block           GC_IND_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7134044.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134044
_shelx_shelxl_version_number     2019/1
_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.
;
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
O1_1 O 0.80913(9) 0.52741(11) 0.11174(10) 0.0483(3) Uani 1 1 d . . . . .
N1_1 N 0.48041(10) 0.52828(13) 0.16331(12) 0.0433(4) Uani 1 1 d . . . . .
N2_1 N 0.76959(11) 0.68827(13) 0.36144(12) 0.0406(4) Uani 1 1 d . . . . .
H1_1 H 0.7311(15) 0.7146(19) 0.3978(18) 0.061 Uiso 1 1 d . U . . .
C1_1 C 0.77714(11) 0.45835(15) 0.35409(14) 0.0375(4) Uani 1 1 d . . . . .
C2_1 C 0.76588(13) 0.34572(16) 0.29549(16) 0.0462(4) Uani 1 1 d . . . . .
H2_1 H 0.735757 0.343082 0.215456 0.055 Uiso 1 1 calc R U . . .
C3_1 C 0.79866(14) 0.23751(17) 0.35408(19) 0.0562(5) Uani 1 1 d . . . . .
H3_1 H 0.790584 0.162727 0.313351 0.067 Uiso 1 1 calc R U . . .
C4_1 C 0.84321(15) 0.2396(2) 0.4723(2) 0.0656(6) Uani 1 1 d . . . . .
H4_1 H 0.864935 0.166546 0.511941 0.079 Uiso 1 1 calc R U . . .
C5_1 C 0.85530(17) 0.3497(2) 0.5311(2) 0.0731(7) Uani 1 1 d . . . . .
H5_1 H 0.885870 0.351487 0.611034 0.088 Uiso 1 1 calc R U . . .
C6_1 C 0.82255(15) 0.45927(19) 0.47317(16) 0.0560(5) Uani 1 1 d . . . . .
H6_1 H 0.831131 0.533679 0.514503 0.067 Uiso 1 1 calc R U . . .
C7_1 C 0.74435(11) 0.57843(14) 0.28610(13) 0.0347(4) Uani 1 1 d . . . . .
C8_1 C 0.63862(11) 0.57841(14) 0.22316(13) 0.0352(4) Uani 1 1 d . . . . .
C9_1 C 0.56826(12) 0.49559(15) 0.23420(14) 0.0397(4) Uani 1 1 d . . . . .
H9_1 H 0.578532 0.426419 0.283139 0.048 Uiso 1 1 calc R U . . .
C10_1 C 0.39007(14) 0.4597(2) 0.15000(19) 0.0594(5) Uani 1 1 d . . . . .
H10A_1 H 0.356395 0.459248 0.068219 0.089 Uiso 1 1 calc R U . . .
H10B_1 H 0.349858 0.498194 0.196376 0.089 Uiso 1 1 calc R U . . .
H10C_1 H 0.404172 0.376129 0.176583 0.089 Uiso 1 1 calc R U . . .
C11_1 C 0.49300(12) 0.63474(16) 0.10363(14) 0.0414(4) Uani 1 1 d . . . . .
C12_1 C 0.42564(14) 0.70132(19) 0.02033(16) 0.0544(5) Uani 1 1 d . . . . .
H12_1 H 0.360861 0.676666 -0.002528 0.065 Uiso 1 1 calc R U . . .
C13_1 C 0.45883(17) 0.8048(2) -0.02659(18) 0.0633(6) Uani 1 1 d . . . . .
H13_1 H 0.415556 0.850960 -0.082680 0.076 Uiso 1 1 calc R U . . .
C14_1 C 0.55581(16) 0.84259(18) 0.00756(17) 0.0581(5) Uani 1 1 d . . . . .
H14_1 H 0.575707 0.913402 -0.025983 0.070 Uiso 1 1 calc R U . . .
C15_1 C 0.62262(14) 0.77699(16) 0.09005(15) 0.0460(4) Uani 1 1 d . . . . .
H15_1 H 0.686996 0.803286 0.112758 0.055 Uiso 1 1 calc R U . . .
C16_1 C 0.59169(12) 0.66954(15) 0.13929(13) 0.0372(4) Uani 1 1 d . . . . .
C17_1 C 0.81056(11) 0.59595(14) 0.19549(13) 0.0350(4) Uani 1 1 d . . . . .
C18_1 C 0.86833(11) 0.70624(14) 0.23059(14) 0.0355(4) Uani 1 1 d . . . . .
C19_1 C 0.83788(11) 0.76017(14) 0.32549(13) 0.0355(4) Uani 1 1 d . . . . .
C20_1 C 0.87566(13) 0.87379(15) 0.37081(15) 0.0446(4) Uani 1 1 d . . . . .
H20_1 H 0.854831 0.911647 0.432740 0.054 Uiso 1 1 calc R U . . .
C21_1 C 0.94493(13) 0.92790(17) 0.32049(17) 0.0519(5) Uani 1 1 d . . . . .
H21_1 H 0.971823 1.003080 0.350453 0.062 Uiso 1 1 calc R U . . .
C22_1 C 0.97639(13) 0.87423(18) 0.22616(17) 0.0512(5) Uani 1 1 d . . . . .
H22_1 H 1.023468 0.913626 0.194612 0.061 Uiso 1 1 calc R U . . .
C23_1 C 0.93811(12) 0.76390(16) 0.18011(15) 0.0431(4) Uani 1 1 d . . . . .
H23_1 H 0.957993 0.727934 0.116641 0.052 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 0.0033 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'
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
C9_1 N1_1 C11_1 108.45(14) . . ?
C9_1 N1_1 C10_1 125.78(15) . . ?
C11_1 N1_1 C10_1 125.74(15) . . ?
C19_1 N2_1 C7_1 111.62(13) . . ?
C6_1 C1_1 C2_1 118.13(16) . . ?
C6_1 C1_1 C7_1 121.61(15) . . ?
C2_1 C1_1 C7_1 120.19(14) . . ?
C3_1 C2_1 C1_1 120.98(17) . . ?
C4_1 C3_1 C2_1 120.31(19) . . ?
C5_1 C4_1 C3_1 119.44(18) . . ?
C4_1 C5_1 C6_1 120.8(2) . . ?
C1_1 C6_1 C5_1 120.3(2) . . ?
N2_1 C7_1 C8_1 111.66(13) . . ?
N2_1 C7_1 C1_1 111.91(12) . . ?
C8_1 C7_1 C1_1 113.56(13) . . ?
N2_1 C7_1 C17_1 101.58(12) . . ?
C8_1 C7_1 C17_1 110.43(12) . . ?
C1_1 C7_1 C17_1 106.93(12) . . ?
C9_1 C8_1 C16_1 106.29(14) . . ?
C9_1 C8_1 C7_1 128.05(14) . . ?
C16_1 C8_1 C7_1 125.65(14) . . ?
C8_1 C9_1 N1_1 110.64(14) . . ?
N1_1 C11_1 C12_1 129.55(17) . . ?
N1_1 C11_1 C16_1 107.85(14) . . ?
C12_1 C11_1 C16_1 122.59(17) . . ?
C13_1 C12_1 C11_1 117.17(19) . . ?
C12_1 C13_1 C14_1 121.75(18) . . ?
C15_1 C14_1 C13_1 121.22(18) . . ?
C14_1 C15_1 C16_1 118.77(18) . . ?
C15_1 C16_1 C11_1 118.49(15) . . ?
C15_1 C16_1 C8_1 134.74(16) . . ?
C11_1 C16_1 C8_1 106.77(14) . . ?
O1_1 C17_1 C18_1 129.15(15) . . ?
O1_1 C17_1 C7_1 123.82(14) . . ?
C18_1 C17_1 C7_1 107.02(13) . . ?
C19_1 C18_1 C23_1 120.95(15) . . ?
C19_1 C18_1 C17_1 108.16(13) . . ?
C23_1 C18_1 C17_1 130.69(15) . . ?
N2_1 C19_1 C20_1 128.20(15) . . ?
N2_1 C19_1 C18_1 111.39(14) . . ?
C20_1 C19_1 C18_1 120.41(15) . . ?
C21_1 C20_1 C19_1 117.49(16) . . ?
C20_1 C21_1 C22_1 122.50(17) . . ?
C23_1 C22_1 C21_1 120.10(17) . . ?
C22_1 C23_1 C18_1 118.53(16) . . ?
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_1 C17_1 1.2181(18) . ?
N1_1 C9_1 1.369(2) . ?
N1_1 C11_1 1.375(2) . ?
N1_1 C10_1 1.451(2) . ?
N2_1 C19_1 1.373(2) . ?
N2_1 C7_1 1.469(2) . ?
C1_1 C6_1 1.385(2) . ?
C1_1 C2_1 1.385(2) . ?
C1_1 C7_1 1.534(2) . ?
C2_1 C3_1 1.379(2) . ?
C3_1 C4_1 1.374(3) . ?
C4_1 C5_1 1.363(3) . ?
C5_1 C6_1 1.388(3) . ?
C7_1 C8_1 1.504(2) . ?
C7_1 C17_1 1.567(2) . ?
C8_1 C9_1 1.363(2) . ?
C8_1 C16_1 1.436(2) . ?
C11_1 C12_1 1.392(2) . ?
C11_1 C16_1 1.409(2) . ?
C12_1 C13_1 1.371(3) . ?
C13_1 C14_1 1.395(3) . ?
C14_1 C15_1 1.377(3) . ?
C15_1 C16_1 1.406(2) . ?
C17_1 C18_1 1.449(2) . ?
C18_1 C19_1 1.396(2) . ?
C18_1 C23_1 1.399(2) . ?
C19_1 C20_1 1.393(2) . ?
C20_1 C21_1 1.376(3) . ?
C21_1 C22_1 1.396(3) . ?
C22_1 C23_1 1.366(2) . ?
