#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:31:09 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243785.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_7243785
loop_
_publ_author_name
'Chen, Wei-Li'
'Li, Kun'
'Liao, Wei-Cong'
'Liang, Wang-Fu'
'Qiu, Pei-Wen'
'Liang, Cui'
'Su, Gui-Fa'
'Mo, Dong-Liang'
_publ_section_title
;
 An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles
 with benzylamines to prepare 3-aminoindole derivatives
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9610
_journal_page_last               9616
_journal_paper_doi               10.1039/D1GC02849A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-08 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.689(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9106(3)
_cell_length_b                   10.4113(4)
_cell_length_c                   18.0346(9)
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9170
_cell_measurement_theta_min      3.7360
_cell_volume                     1468.28(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6002    0.0000  -90.0000 177

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9283  178.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00    5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9283  -99.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0261615000
_diffrn_orient_matrix_UB_12      -0.0144516000
_diffrn_orient_matrix_UB_13      -0.0349776000
_diffrn_orient_matrix_UB_21      0.0384559000
_diffrn_orient_matrix_UB_22      0.0615028000
_diffrn_orient_matrix_UB_23      -0.0003596000
_diffrn_orient_matrix_UB_31      0.0778750000
_diffrn_orient_matrix_UB_32      -0.0255255000
_diffrn_orient_matrix_UB_33      0.0189474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10925
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         3.258
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0639
_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)+(0.0476P)²+0.3851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2003
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc02849a2.cif
_cod_data_source_block           20180605_mdl_cwl_6_57
_cod_depositor_comments
'Adding full bibliography for 7243784--7243785.cif.'
_cod_database_code               7243785
_shelx_shelxl_version_number     2014/7
_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.
;
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C10(H10), C4(H4), C18(H18), C2(H2), C3(H3), C5(H5), C11(H11),
 C19(H19), C16(H16), C14(H14), C17(H17), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.7708(2) 0.52243(16) 0.04443(10) 0.0482(5) Uani 1 1 d . . . . .
N2 N 0.4644(2) 0.42326(16) 0.15554(10) 0.0487(5) Uani 1 1 d . . . . .
C7 C 0.5725(2) 0.42585(18) 0.10961(11) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.6747(2) 0.54472(18) 0.09504(11) 0.0408(5) Uani 1 1 d . . . . .
C1 C 0.7443(2) 0.39263(19) 0.02047(12) 0.0441(5) Uani 1 1 d . . . . .
C9 C 0.6712(2) 0.67199(18) 0.13015(12) 0.0425(5) Uani 1 1 d . . . . .
C15 C 0.3704(3) 0.30896(19) 0.16398(12) 0.0447(5) Uani 1 1 d . . . . .
C6 C 0.6291(2) 0.32836(18) 0.05890(11) 0.0403(5) Uani 1 1 d . . . . .
C20 C 0.4190(3) 0.2300(2) 0.22475(13) 0.0553(6) Uani 1 1 d . . . . .
H20 H 0.5149 0.2502 0.2593 0.066 Uiso 1 1 calc R . . . .
C10 C 0.7559(3) 0.7737(2) 0.10126(13) 0.0500(6) Uani 1 1 d . . . . .
H10 H 0.8134 0.7595 0.0607 0.060 Uiso 1 1 calc R . . . .
C4 C 0.6687(3) 0.1412(2) -0.01230(13) 0.0560(6) Uani 1 1 d . . . . .
H4 H 0.6446 0.0554 -0.0237 0.067 Uiso 1 1 calc R . . . .
C18 C 0.1839(3) 0.0907(2) 0.18388(14) 0.0581(6) Uani 1 1 d . . . . .
H18 H 0.1232 0.0158 0.1897 0.070 Uiso 1 1 calc R . . . .
C2 C 0.8205(3) 0.3341(2) -0.03389(13) 0.0574(6) Uani 1 1 d . . . . .
H2 H 0.8972 0.3782 -0.0589 0.069 Uiso 1 1 calc R . . . .
C3 C 0.7796(3) 0.2066(2) -0.05040(13) 0.0593(6) Uani 1 1 d . . . . .
H3 H 0.8279 0.1649 -0.0877 0.071 Uiso 1 1 calc R . . . .
C5 C 0.5918(3) 0.2009(2) 0.04289(13) 0.0507(6) Uani 1 1 d . . . . .
H5 H 0.5168 0.1560 0.0685 0.061 Uiso 1 1 calc R . . . .
C11 C 0.7557(3) 0.8940(2) 0.13178(14) 0.0587(6) Uani 1 1 d . . . . .
H11 H 0.8125 0.9608 0.1117 0.070 Uiso 1 1 calc R . . . .
C19 C 0.3255(3) 0.1213(2) 0.23438(14) 0.0594(6) Uani 1 1 d . . . . .
H19 H 0.3588 0.0682 0.2755 0.071 Uiso 1 1 calc R . . . .
C16 C 0.2249(3) 0.2808(2) 0.11438(13) 0.0603(6) Uani 1 1 d . . . . .
H16 H 0.1892 0.3352 0.0741 0.072 Uiso 1 1 calc R . . . .
C14 C 0.5879(3) 0.6961(2) 0.19069(14) 0.0588(6) Uani 1 1 d . . . . .
H14 H 0.5308 0.6298 0.2110 0.071 Uiso 1 1 calc R . . . .
C17 C 0.1323(3) 0.1713(2) 0.12471(14) 0.0662(7) Uani 1 1 d . . . . .
H17 H 0.0342 0.1522 0.0912 0.079 Uiso 1 1 calc R . . . .
C12 C 0.6720(3) 0.9167(2) 0.19203(16) 0.0664(7) Uani 1 1 d . . . . .
H12 H 0.6718 0.9986 0.2127 0.080 Uiso 1 1 calc R . . . .
C13 C 0.5886(3) 0.8177(2) 0.22138(16) 0.0720(7) Uani 1 1 d . . . . .
H13 H 0.5321 0.8326 0.2622 0.086 Uiso 1 1 calc R . . . .
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'
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 N1 C1 107.97(16) . . ?
C7 N2 C15 119.89(17) . . ?
N2 C7 C8 123.64(18) . . ?
N2 C7 C6 132.89(17) . . ?
C6 C7 C8 103.46(16) . . ?
N1 C8 C7 111.10(17) . . ?
N1 C8 C9 121.09(18) . . ?
C9 C8 C7 127.80(18) . . ?
C6 C1 N1 112.42(18) . . ?
C2 C1 N1 125.36(18) . . ?
C2 C1 C6 122.21(19) . . ?
C10 C9 C8 118.79(19) . . ?
C14 C9 C8 123.11(18) . . ?
C14 C9 C10 118.09(19) . . ?
C20 C15 N2 119.77(18) . . ?
C20 C15 C16 119.65(19) . . ?
C16 C15 N2 120.46(19) . . ?
C1 C6 C7 105.02(16) . . ?
C5 C6 C7 135.51(19) . . ?
C5 C6 C1 119.46(19) . . ?
C15 C20 C19 120.0(2) . . ?
C11 C10 C9 121.0(2) . . ?
C3 C4 C5 121.2(2) . . ?
C17 C18 C19 119.5(2) . . ?
C1 C2 C3 117.7(2) . . ?
C4 C3 C2 120.8(2) . . ?
C6 C5 C4 118.5(2) . . ?
C10 C11 C12 120.3(2) . . ?
C18 C19 C20 120.5(2) . . ?
C15 C16 C17 119.7(2) . . ?
C9 C14 C13 120.6(2) . . ?
C18 C17 C16 120.6(2) . . ?
C13 C12 C11 119.5(2) . . ?
C12 C13 C14 120.5(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
N1 C8 1.294(2) . ?
N1 C1 1.425(3) . ?
N2 C7 1.278(2) . ?
N2 C15 1.423(2) . ?
C7 C8 1.523(3) . ?
C7 C6 1.480(3) . ?
C8 C9 1.471(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.370(3) . ?
C9 C10 1.396(3) . ?
C9 C14 1.381(3) . ?
C15 C20 1.377(3) . ?
C15 C16 1.379(3) . ?
C6 C5 1.381(3) . ?
C20 C19 1.377(3) . ?
C10 C11 1.368(3) . ?
C4 C3 1.374(3) . ?
C4 C5 1.389(3) . ?
C18 C19 1.371(3) . ?
C18 C17 1.370(3) . ?
C2 C3 1.388(3) . ?
C11 C12 1.376(3) . ?
C16 C17 1.383(3) . ?
C14 C13 1.382(3) . ?
C12 C13 1.373(3) . ?
