#------------------------------------------------------------------------------
#$Date: 2021-10-06 16:53:02 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/88/7128895.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_7128895
loop_
_publ_author_name
'Liu, Xiaoyu'
'He, Kun'
'Gao, Na'
'Jiang, Peiyun'
'Lin, Jun'
'Jin, Yi'
_publ_section_title
;
 A radical-mediated multicomponent cascade reaction for the synthesis of
 azide-biindole derivatives.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9696
_journal_page_last               9699
_journal_paper_doi               10.1039/d1cc03853b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         C23H15N7
_chemical_formula_sum            'C23 H15 N7'
_chemical_formula_weight         527.04
_chemical_melting_point          486
_chemical_name_systematic
3'-azido-2'-(1H-benzo[d]imidazol-1-yl)-1H,3'H-3,3'-biindole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc284vlw
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-06-15 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                91.808(2)
_cell_angle_beta                 111.391(2)
_cell_angle_gamma                101.478(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6842(17)
_cell_length_b                   10.8749(17)
_cell_length_c                   12.429(2)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.57
_cell_measurement_theta_min      2.46
_cell_volume                     1309.1(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12261
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         1.923
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexyl hydride'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5904
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0669
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3171
_reflns_number_total             5904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03853b2.cif
_cod_data_source_block           hz_2_0m_a_sq
_cod_depositor_comments
'Adding full bibliography for 7128895--7128897.cif.'
_cod_original_formula_sum        C23H15N7
_cod_database_code               7128895
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
N2 N 0.5837(2) 0.72375(19) 0.1132(2) 0.0898(7) Uani 1 1 d . . . . .
N3 N 0.66621(19) 0.25192(18) 0.07760(16) 0.0727(6) Uani 1 1 d . . . . .
H3A H 0.592359 0.221679 0.017530 0.087 Uiso 1 1 calc R U . . .
N4 N 0.84533(16) 0.38781(16) 0.20888(14) 0.0581(5) Uani 1 1 d . . . . .
N5 N 1.04123(17) 0.51129(17) 0.35630(15) 0.0641(5) Uani 1 1 d . . . . .
N6 N 1.1380(5) 0.6632(5) 0.0800(4) 0.208(2) Uani 1 1 d . U . . .
N7 N 1.0380(4) 0.6434(3) 0.0925(2) 0.1063(8) Uani 1 1 d . . . . .
N8 N 0.9255(3) 0.6171(2) 0.09333(18) 0.0934(7) Uani 1 1 d . . . . .
C1 C 0.6945(3) 0.6982(2) 0.0953(2) 0.0794(7) Uani 1 1 d . . . . .
H1 H 0.709249 0.706152 0.026342 0.095 Uiso 1 1 calc R U . . .
C2 C 0.7191(2) 0.6605(2) 0.2771(2) 0.0650(6) Uani 1 1 d . . . . .
C3 C 0.7562(3) 0.6326(3) 0.3919(2) 0.0830(8) Uani 1 1 d . . . . .
H3 H 0.836507 0.604463 0.428149 0.100 Uiso 1 1 calc R U . . .
C4 C 0.6726(3) 0.6473(4) 0.4501(3) 0.1241(12) Uani 1 1 d . . . . .
H4 H 0.695921 0.628115 0.526408 0.149 Uiso 1 1 calc R U . . .
C5 C 0.5531(4) 0.6906(5) 0.3966(4) 0.1428(15) Uani 1 1 d . . . . .
H5 H 0.499327 0.701629 0.438855 0.171 Uiso 1 1 calc R U . . .
C6 C 0.5122(3) 0.7175(3) 0.2844(4) 0.1160(11) Uani 1 1 d . . . . .
H6 H 0.431135 0.744871 0.248935 0.139 Uiso 1 1 calc R U . . .
C7 C 0.5961(2) 0.7022(2) 0.2259(3) 0.0801(7) Uani 1 1 d . . . . .
C8 C 0.9360(2) 0.5025(2) 0.26338(18) 0.0566(5) Uani 1 1 d . . . . .
C9 C 0.9159(2) 0.6273(2) 0.21047(17) 0.0621(6) Uani 1 1 d . . . . .
C10 C 1.0397(2) 0.7143(2) 0.30211(19) 0.0641(6) Uani 1 1 d . . . . .
C11 C 1.0887(3) 0.8421(3) 0.3122(2) 0.0831(7) Uani 1 1 d . . . . .
H11 H 1.042958 0.891155 0.257867 0.100 Uiso 1 1 calc R U . . .
C12 C 1.2103(3) 0.8965(3) 0.4075(3) 0.0974(9) Uani 1 1 d . . . . .
H12 H 1.246458 0.983056 0.416423 0.117 Uiso 1 1 calc R U . . .
C13 C 1.2762(3) 0.8241(3) 0.4872(3) 0.0947(9) Uani 1 1 d . . . . .
H13 H 1.356016 0.862669 0.550020 0.114 Uiso 1 1 calc R U . . .
C14 C 1.2279(2) 0.6953(3) 0.4773(2) 0.0810(7) Uani 1 1 d . . . . .
H14 H 1.273843 0.646558 0.531781 0.097 Uiso 1 1 calc R U . . .
C15 C 1.1085(2) 0.6414(2) 0.38327(19) 0.0647(6) Uani 1 1 d . . . . .
C16 C 0.7303(2) 0.3685(2) 0.10861(19) 0.0662(6) Uani 1 1 d . . . . .
H16 H 0.701075 0.433693 0.066649 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7413(2) 0.1853(2) 0.16142(19) 0.0647(6) Uani 1 1 d . . . . .
C18 C 0.8539(2) 0.2675(2) 0.24492(18) 0.0580(5) Uani 1 1 d . . . . .
C19 C 0.9475(2) 0.2265(2) 0.33860(19) 0.0707(6) Uani 1 1 d . . . . .
H19 H 1.023174 0.282270 0.393662 0.085 Uiso 1 1 calc R U . . .
C20 C 0.9221(3) 0.0998(3) 0.3455(2) 0.0890(8) Uani 1 1 d . . . . .
H20 H 0.982656 0.067940 0.406747 0.107 Uiso 1 1 calc R U . . .
C21 C 0.8082(3) 0.0166(3) 0.2634(3) 0.0951(9) Uani 1 1 d . . . . .
H21 H 0.794110 -0.069126 0.271868 0.114 Uiso 1 1 calc R U . . .
C22 C 0.7173(3) 0.0571(2) 0.1714(3) 0.0867(8) Uani 1 1 d . . . . .
H22 H 0.641479 0.000860 0.116972 0.104 Uiso 1 1 calc R U . . .
C23 C 0.7812(2) 0.65906(19) 0.19237(18) 0.0615(6) 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'
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
C1 N2 C7 108.9(2) . . ?
C16 N3 C17 105.50(18) . . ?
C16 N3 H3A 127.3 . . ?
C17 N3 H3A 127.3 . . ?
C16 N4 C8 127.26(18) . . ?
C16 N4 C18 105.63(17) . . ?
C8 N4 C18 127.11(17) . . ?
C8 N5 C15 106.35(18) . . ?
N6 N7 N8 172.8(4) . . ?
N7 N8 C9 116.1(2) . . ?
N2 C1 C23 110.8(2) . . ?
N2 C1 H1 124.6 . . ?
C23 C1 H1 124.6 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C23 134.2(2) . . ?
C7 C2 C23 107.5(2) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.9(3) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
C6 C7 N2 130.3(3) . . ?
C6 C7 C2 122.8(3) . . ?
N2 C7 C2 106.8(3) . . ?
N5 C8 N4 122.88(19) . . ?
N5 C8 C9 115.95(19) . . ?
N4 C8 C9 121.14(17) . . ?
C23 C9 N8 106.65(18) . . ?
C23 C9 C10 115.14(18) . . ?
N8 C9 C10 113.73(19) . . ?
C23 C9 C8 115.35(17) . . ?
N8 C9 C8 108.18(18) . . ?
C10 C9 C8 97.68(16) . . ?
C11 C10 C15 121.0(2) . . ?
C11 C10 C9 131.0(2) . . ?
C15 C10 C9 108.0(2) . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 117.4(2) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 N5 126.8(2) . . ?
C10 C15 N5 112.02(19) . . ?
N3 C16 N4 113.90(19) . . ?
N3 C16 H16 123.0 . . ?
N4 C16 H16 123.0 . . ?
C22 C17 N3 129.8(2) . . ?
C22 C17 C18 120.0(2) . . ?
N3 C17 C18 110.2(2) . . ?
C19 C18 C17 122.6(2) . . ?
C19 C18 N4 132.6(2) . . ?
C17 C18 N4 104.80(17) . . ?
C20 C19 C18 116.1(2) . . ?
C20 C19 H19 122.0 . . ?
C18 C19 H19 122.0 . . ?
C19 C20 C21 121.9(2) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C17 117.6(2) . . ?
C21 C22 H22 121.2 . . ?
C17 C22 H22 121.2 . . ?
C1 C23 C2 106.0(2) . . ?
C1 C23 C9 127.8(2) . . ?
C2 C23 C9 126.20(17) . . ?
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
N2 C1 1.359(3) . ?
N2 C7 1.390(4) . ?
N3 C16 1.287(3) . ?
N3 C17 1.387(3) . ?
N3 H3A 0.8600 . ?
N4 C16 1.368(3) . ?
N4 C8 1.393(3) . ?
N4 C18 1.406(3) . ?
N5 C8 1.269(2) . ?
N5 C15 1.421(3) . ?
N6 N7 1.115(4) . ?
N7 N8 1.184(3) . ?
N8 C9 1.499(3) . ?
C1 C23 1.367(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(3) . ?
C2 C7 1.408(3) . ?
C2 C23 1.436(3) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.546(3) . ?
C9 C23 1.486(3) . ?
C9 C10 1.509(3) . ?
C10 C11 1.368(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.403(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.384(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.362(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.355(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
