#------------------------------------------------------------------------------
#$Date: 2024-09-27 04:27:44 +0300 (Fri, 27 Sep 2024) $
#$Revision: 294919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249400.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_7249400
loop_
_publ_author_name
'Zhang, Hong'
'Jiang, Yunhe'
'Sun, Xiaoxue'
'Liang, Tianyu'
'Wang, Xiang'
'Li, Yang'
_publ_section_title
;
 A new synthesis of indolo[2,3-b]quinolines from
 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              30707
_journal_page_last               30712
_journal_paper_doi               10.1039/D4RA05176A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C24 H19 Cl N2'
_chemical_formula_sum            'C24 H19 Cl N2'
_chemical_formula_weight         370.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-07-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.5868(4)
_cell_length_b                   13.6623(6)
_cell_length_c                   31.9980(16)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.912
_cell_measurement_theta_min      2.546
_cell_volume                     3753.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            26661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.502
_diffrn_reflns_theta_min         2.546
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0612
_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)+(0.0660P)²+1.9746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             4760
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05176a2.cif
_cod_data_source_block           2
_cod_database_code               7249400
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Me refined with riding coordinates:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C2(H2), C17(H17), C15(H15), C12(H12), C3(H3), C11(H11),
 C13(H13), C14(H14), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
'-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
Cl1 Cl 0.09971(8) 0.47286(5) 0.92778(3) 0.0646(2) Uani 1 1 d . . . . .
N1 N 0.3203(2) 0.16394(14) 0.81455(6) 0.0408(5) Uani 1 1 d . . . . .
C9 C 0.4635(3) 0.14434(15) 0.83220(7) 0.0360(5) Uani 1 1 d . . . . .
C8 C 0.4831(3) 0.20360(15) 0.86872(6) 0.0338(5) Uani 1 1 d . . . . .
N2 N 0.5632(2) 0.08094(13) 0.81695(6) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.7330(3) 0.12894(15) 0.87578(7) 0.0366(5) Uani 1 1 d . . . . .
C7 C 0.6183(3) 0.19516(15) 0.89131(7) 0.0350(5) Uani 1 1 d . . . . .
C16 C 0.3425(2) 0.26180(15) 0.87230(7) 0.0347(5) Uani 1 1 d . . . . .
C10 C 0.6391(2) 0.25058(16) 0.93118(7) 0.0357(5) Uani 1 1 d . . . . .
C21 C 0.2454(3) 0.23689(16) 0.83812(7) 0.0358(5) Uani 1 1 d . . . . .
C20 C 0.1023(3) 0.28383(16) 0.83168(7) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.6992(3) 0.07351(16) 0.83892(7) 0.0387(5) Uani 1 1 d . . . . .
C19 C 0.0634(3) 0.35606(17) 0.86042(8) 0.0450(6) Uani 1 1 d . . . . .
H19 H -0.030089 0.389543 0.857084 0.054 Uiso 1 1 calc R U . . .
C18 C 0.1584(3) 0.38006(16) 0.89383(8) 0.0428(5) Uani 1 1 d . . . . .
C5 C 0.8792(3) 0.11565(18) 0.89543(8) 0.0469(6) Uani 1 1 d . . . . .
H5 H 0.902870 0.151166 0.919395 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8125(3) 0.00628(17) 0.82420(8) 0.0468(6) Uani 1 1 d . . . . .
H2 H 0.791464 -0.031250 0.800616 0.056 Uiso 1 1 calc R U . . .
C17 C 0.2981(3) 0.33344(16) 0.90079(7) 0.0386(5) Uani 1 1 d . . . . .
H17 H 0.360356 0.349216 0.923604 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0093(3) 0.2652(2) 0.79593(8) 0.0503(6) Uani 1 1 d . . . . .
H22A H -0.114924 0.277222 0.805393 0.060 Uiso 1 1 calc R U . . .
H22B H -0.002259 0.196993 0.787684 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5869(4) 0.21037(19) 0.96817(8) 0.0583(7) Uani 1 1 d . . . . .
H15 H 0.546023 0.147319 0.968206 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7080(4) 0.3956(2) 0.96899(10) 0.0660(8) Uani 1 1 d . . . . .
H12 H 0.749142 0.458584 0.969183 0.079 Uiso 1 1 calc R U . . .
C3 C 0.9516(3) -0.00405(19) 0.84410(8) 0.0544(7) Uani 1 1 d . . . . .
H3 H 1.024588 -0.048389 0.833971 0.065 Uiso 1 1 calc R U . . .
C23 C 0.0243(4) 0.3294(2) 0.75826(9) 0.0670(8) Uani 1 1 d . . . . .
H23A H -0.049158 0.315062 0.736476 0.100 Uiso 1 1 calc R U . . .
H23B H 0.015265 0.397008 0.766094 0.100 Uiso 1 1 calc R U . . .
H23C H 0.127910 0.316794 0.748388 0.100 Uiso 1 1 calc R U . . .
C11 C 0.7010(3) 0.34363(19) 0.93192(8) 0.0525(6) Uani 1 1 d . . . . .
H11 H 0.738304 0.371615 0.907384 0.063 Uiso 1 1 calc R U . . .
C24 C 0.2640(3) 0.1100(2) 0.77846(8) 0.0553(7) Uani 1 1 d . . . . .
H24A H 0.162891 0.133815 0.770729 0.083 Uiso 1 1 calc R U . . .
H24B H 0.334795 0.118739 0.755538 0.083 Uiso 1 1 calc R U . . .
H24C H 0.257212 0.041658 0.785265 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6548(4) 0.3550(2) 1.00536(9) 0.0678(8) Uani 1 1 d . . . . .
H13 H 0.659682 0.390206 1.030198 0.081 Uiso 1 1 calc R U . . .
C14 C 0.5943(4) 0.2622(2) 1.00505(9) 0.0711(9) Uani 1 1 d . . . . .
H14 H 0.558236 0.234256 1.029720 0.085 Uiso 1 1 calc R U . . .
C4 C 0.9857(3) 0.05154(19) 0.87971(9) 0.0551(7) Uani 1 1 d . . . . .
H4 H 1.081826 0.044640 0.892746 0.066 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'
Cl Cl 0.1484 0.1585 '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 N1 C21 109.02(18) . . ?
C9 N1 C24 121.6(2) . . ?
C21 N1 C24 129.4(2) . . ?
N1 C9 C8 109.22(19) . . ?
N2 C9 N1 123.9(2) . . ?
N2 C9 C8 126.9(2) . . ?
C9 C8 C16 106.07(18) . . ?
C7 C8 C9 118.81(19) . . ?
C7 C8 C16 135.13(19) . . ?
C9 N2 C1 114.54(19) . . ?
C7 C6 C1 118.8(2) . . ?
C5 C6 C7 122.6(2) . . ?
C5 C6 C1 118.5(2) . . ?
C8 C7 C6 117.0(2) . . ?
C8 C7 C10 120.55(19) . . ?
C6 C7 C10 122.4(2) . . ?
C21 C16 C8 107.30(18) . . ?
C17 C16 C8 131.7(2) . . ?
C17 C16 C21 120.9(2) . . ?
C15 C10 C7 119.5(2) . . ?
C11 C10 C7 121.9(2) . . ?
C11 C10 C15 118.6(2) . . ?
N1 C21 C16 108.37(19) . . ?
C20 C21 N1 130.3(2) . . ?
C20 C21 C16 121.3(2) . . ?
C21 C20 C22 126.1(2) . . ?
C19 C20 C21 116.0(2) . . ?
C19 C20 C22 117.8(2) . . ?
N2 C1 C6 123.9(2) . . ?
N2 C1 C2 117.6(2) . . ?
C2 C1 C6 118.5(2) . . ?
C20 C19 H19 118.7 . . ?
C18 C19 C20 122.5(2) . . ?
C18 C19 H19 118.7 . . ?
C19 C18 Cl1 118.87(18) . . ?
C17 C18 Cl1 119.19(19) . . ?
C17 C18 C19 121.9(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C16 C17 H17 121.4 . . ?
C18 C17 C16 117.3(2) . . ?
C18 C17 H17 121.4 . . ?
C20 C22 H22A 109.1 . . ?
C20 C22 H22B 109.1 . . ?
C20 C22 C23 112.5(2) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
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
Cl1 C18 1.744(2) . ?
N1 C9 1.379(3) . ?
N1 C21 1.406(3) . ?
N1 C24 1.453(3) . ?
C9 C8 1.432(3) . ?
C9 N2 1.312(3) . ?
C8 C7 1.372(3) . ?
C8 C16 1.450(3) . ?
N2 C1 1.367(3) . ?
C6 C7 1.427(3) . ?
C6 C1 1.431(3) . ?
C6 C5 1.416(3) . ?
C7 C10 1.494(3) . ?
C16 C21 1.417(3) . ?
C16 C17 1.391(3) . ?
C10 C15 1.380(3) . ?
C10 C11 1.378(3) . ?
C21 C20 1.401(3) . ?
C20 C19 1.390(3) . ?
C20 C22 1.514(3) . ?
C1 C2 1.419(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.384(3) . ?
C18 C17 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.362(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.361(4) . ?
C17 H17 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.519(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.384(4) . ?
C12 C13 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C11 H11 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C17 C16 -178.24(17) . . . . ?
N1 C9 C8 C7 179.67(19) . . . . ?
N1 C9 C8 C16 -0.4(2) . . . . ?
N1 C9 N2 C1 179.2(2) . . . . ?
N1 C21 C20 C19 -177.9(2) . . . . ?
N1 C21 C20 C22 0.0(4) . . . . ?
C9 N1 C21 C16 -1.7(2) . . . . ?
C9 N1 C21 C20 176.9(2) . . . . ?
C9 C8 C7 C6 1.8(3) . . . . ?
C9 C8 C7 C10 -175.86(19) . . . . ?
C9 C8 C16 C21 -0.7(2) . . . . ?
C9 C8 C16 C17 -178.1(2) . . . . ?
C9 N2 C1 C6 0.4(3) . . . . ?
C9 N2 C1 C2 -180.0(2) . . . . ?
C8 C9 N2 C1 -0.6(3) . . . . ?
C8 C7 C10 C15 87.0(3) . . . . ?
C8 C7 C10 C11 -89.2(3) . . . . ?
C8 C16 C21 N1 1.5(2) . . . . ?
C8 C16 C21 C20 -177.35(19) . . . . ?
C8 C16 C17 C18 175.8(2) . . . . ?
N2 C9 C8 C7 -0.5(3) . . . . ?
N2 C9 C8 C16 179.5(2) . . . . ?
N2 C1 C2 C3 179.0(2) . . . . ?
C6 C7 C10 C15 -90.6(3) . . . . ?
C6 C7 C10 C11 93.3(3) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C5 C4 C3 -1.2(4) . . . . ?
C7 C8 C16 C21 179.3(2) . . . . ?
C7 C8 C16 C17 1.8(4) . . . . ?
C7 C6 C1 N2 1.0(3) . . . . ?
C7 C6 C1 C2 -178.7(2) . . . . ?
C7 C6 C5 C4 179.9(2) . . . . ?
C7 C10 C15 C14 -175.4(3) . . . . ?
C7 C10 C11 C12 175.2(3) . . . . ?
C16 C8 C7 C6 -178.1(2) . . . . ?
C16 C8 C7 C10 4.2(4) . . . . ?
C16 C21 C20 C19 0.6(3) . . . . ?
C16 C21 C20 C22 178.6(2) . . . . ?
C10 C15 C14 C13 -0.3(5) . . . . ?
C21 N1 C9 C8 1.3(2) . . . . ?
C21 N1 C9 N2 -178.5(2) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C21 C20 C19 C18 -0.7(3) . . . . ?
C21 C20 C22 C23 -89.2(3) . . . . ?
C20 C19 C18 Cl1 179.28(18) . . . . ?
C20 C19 C18 C17 -0.2(4) . . . . ?
C1 C6 C7 C8 -2.0(3) . . . . ?
C1 C6 C7 C10 175.57(19) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C19 C20 C22 C23 88.7(3) . . . . ?
C19 C18 C17 C16 1.2(3) . . . . ?
C5 C6 C7 C8 178.1(2) . . . . ?
C5 C6 C7 C10 -4.3(3) . . . . ?
C5 C6 C1 N2 -179.1(2) . . . . ?
C5 C6 C1 C2 1.2(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C17 C16 C21 N1 179.25(19) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
C22 C20 C19 C18 -178.9(2) . . . . ?
C15 C10 C11 C12 -1.0(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C11 C10 C15 C14 0.8(4) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C24 N1 C9 C8 -176.0(2) . . . . ?
C24 N1 C9 N2 4.1(3) . . . . ?
C24 N1 C21 C16 175.3(2) . . . . ?
C24 N1 C21 C20 -6.0(4) . . . . ?
C13 C12 C11 C10 0.6(5) . . . . ?
