#------------------------------------------------------------------------------
#$Date: 2022-04-26 01:02:43 +0300 (Tue, 26 Apr 2022) $
#$Revision: 274666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/00/7130010.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_7130010
loop_
_publ_author_name
'Yashmin, Sabina'
'Ali, Rashid'
'Mondal, Santa'
'Khan, Abu Taleb'
_publ_section_title
;
 DMSO-assisted environmentally benign synthesis of
 benzo[c]-chromeno[4,3,2-gh]phenanthridines by remote oxidative hetero
 cross-coupling cyclization and aromatization reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01067D
_journal_year                    2022
_chemical_formula_sum            'C27 H21 N O'
_chemical_formula_weight         375.45
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-02-18 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.915(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9415(9)
_cell_length_b                   20.8156(11)
_cell_length_c                   11.0217(8)
_cell_measurement_reflns_used    957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.6050
_cell_measurement_theta_min      2.6110
_cell_volume                     1928.7(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6743
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.547
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       Plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.985
_exptl_transmission_factor_min   0.963
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0646
_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)+(0.0601P)²+0.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1709
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01067d2.cif
_cod_data_source_block           ra5
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7130010
_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.
;
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
O1 O 0.4614(3) 0.38245(9) 0.45388(16) 0.0507(6) Uani 1 1 d . . . . .
N1 N 0.6167(3) 0.53386(11) 0.28325(19) 0.0397(6) Uani 1 1 d . . . . .
C23 C 0.6634(4) 0.46070(12) 0.4593(2) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.5652(3) 0.48489(13) 0.3329(2) 0.0358(7) Uani 1 1 d . . . . .
C2 C 0.4169(3) 0.45361(13) 0.2717(2) 0.0362(7) Uani 1 1 d . . . . .
C3 C 0.3196(4) 0.47409(13) 0.1485(2) 0.0410(8) Uani 1 1 d . . . . .
C17 C 0.3678(3) 0.40176(13) 0.3315(2) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.3766(4) 0.52757(14) 0.0930(2) 0.0405(8) Uani 1 1 d . . . . .
C18 C 0.6070(4) 0.41064(13) 0.5146(2) 0.0402(8) Uani 1 1 d . . . . .
C16 C 0.2273(4) 0.36821(14) 0.2739(3) 0.0424(8) Uani 1 1 d . . . . .
C13 C 0.5222(4) 0.55527(13) 0.1634(2) 0.0395(7) Uani 1 1 d . . . . .
C22 C 0.8138(4) 0.48500(14) 0.5286(2) 0.0450(8) Uani 1 1 d . . . . .
H22 H 0.8558 0.5182 0.4937 0.054 Uiso 1 1 calc R U . . .
C19 C 0.6916(4) 0.38610(14) 0.6350(2) 0.0479(8) Uani 1 1 d . . . . .
H19 H 0.6497 0.3533 0.6710 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7260(4) 0.63935(14) 0.1803(3) 0.0497(9) Uani 1 1 d . . . . .
H11 H 0.7867 0.6239 0.2613 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5811(4) 0.60952(14) 0.1116(3) 0.0435(8) Uani 1 1 d . . . . .
C15 C 0.1348(4) 0.39056(15) 0.1516(3) 0.0515(9) Uani 1 1 d . . . . .
H15 H 0.0390 0.3698 0.1092 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1770(4) 0.44121(14) 0.0907(3) 0.0485(9) Uani 1 1 d . . . . .
H14 H 0.1095 0.4539 0.0096 0.058 Uiso 1 1 calc R U . . .
C20 C 0.8392(4) 0.41134(15) 0.7002(3) 0.0527(9) Uani 1 1 d . . . . .
H20 H 0.8983 0.3950 0.7808 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4909(4) 0.63317(15) -0.0118(3) 0.0507(9) Uani 1 1 d . . . . .
C21 C 0.9012(4) 0.46052(15) 0.6482(2) 0.0519(9) Uani 1 1 d . . . . .
H21 H 1.0013 0.4771 0.6935 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1776(4) 0.31041(15) 0.3381(3) 0.0519(9) Uani 1 1 d . . . . .
C5 C 0.2901(4) 0.55233(15) -0.0316(3) 0.0515(9) Uani 1 1 d . . . . .
H5 H 0.1937 0.5336 -0.0798 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3458(4) 0.60246(16) -0.0805(3) 0.0565(10) Uani 1 1 d . . . . .
H6 H 0.2868 0.6174 -0.1624 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5492(5) 0.68637(17) -0.0608(3) 0.0656(11) Uani 1 1 d . . . . .
H8 H 0.4902 0.7025 -0.1417 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7790(5) 0.69116(15) 0.1291(3) 0.0628(10) Uani 1 1 d . . . . .
H10 H 0.8750 0.7106 0.1757 0.075 Uiso 1 1 calc R U . . .
C25 C 0.3056(4) 0.25783(15) 0.3690(3) 0.0655(10) Uani 1 1 d . . . . .
H25A H 0.3271 0.2467 0.2920 0.098 Uiso 1 1 calc R U . . .
H25B H 0.2685 0.2205 0.4014 0.098 Uiso 1 1 calc R U . . .
H25C H 0.4013 0.2733 0.4329 0.098 Uiso 1 1 calc R U . . .
C9 C 0.6895(5) 0.71471(17) 0.0073(3) 0.0707(11) Uani 1 1 d . . . . .
H9 H 0.7259 0.7497 -0.0270 0.085 Uiso 1 1 calc R U . . .
C26 C 0.0234(4) 0.27979(16) 0.2490(3) 0.0704(11) Uani 1 1 d . . . . .
H26A H -0.0614 0.3106 0.2301 0.106 Uiso 1 1 calc R U . . .
H26B H -0.0024 0.2431 0.2909 0.106 Uiso 1 1 calc R U . . .
H26C H 0.0374 0.2665 0.1701 0.106 Uiso 1 1 calc R U . . .
C27 C 0.1487(5) 0.33190(17) 0.4620(3) 0.0919(15) Uani 1 1 d . . . . .
H27A H 0.2414 0.3537 0.5176 0.138 Uiso 1 1 calc R U . . .
H27B H 0.1276 0.2949 0.5057 0.138 Uiso 1 1 calc R U . . .
H27C H 0.0591 0.3605 0.4400 0.138 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
C18 O1 C17 120.6(2) . . ?
C1 N1 C13 117.6(3) . . ?
C18 C23 C22 117.3(2) . . ?
C18 C23 C1 119.2(3) . . ?
C22 C23 C1 123.5(3) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 C23 118.9(3) . . ?
C2 C1 C23 117.0(2) . . ?
C3 C2 C17 119.6(3) . . ?
C3 C2 C1 119.2(3) . . ?
C17 C2 C1 121.1(2) . . ?
C14 C3 C2 117.4(3) . . ?
C14 C3 C4 125.8(3) . . ?
C2 C3 C4 116.8(3) . . ?
O1 C17 C16 116.9(3) . . ?
O1 C17 C2 119.8(3) . . ?
C16 C17 C2 123.3(2) . . ?
C13 C4 C5 119.0(3) . . ?
C13 C4 C3 118.7(2) . . ?
C5 C4 C3 122.2(3) . . ?
O1 C18 C19 115.3(3) . . ?
O1 C18 C23 122.2(2) . . ?
C19 C18 C23 122.5(3) . . ?
C17 C16 C15 114.8(3) . . ?
C17 C16 C24 122.8(3) . . ?
C15 C16 C24 122.4(3) . . ?
N1 C13 C4 123.5(3) . . ?
N1 C13 C12 116.4(3) . . ?
C4 C13 C12 120.1(2) . . ?
C21 C22 C23 121.0(3) . . ?
C20 C19 C18 118.4(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 C13 121.8(3) . . ?
C7 C12 C13 119.2(3) . . ?
C14 C15 C16 123.8(3) . . ?
C15 C14 C3 121.0(3) . . ?
C19 C20 C21 121.2(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 122.9(3) . . ?
C12 C7 C6 118.5(3) . . ?
C20 C21 C22 119.6(3) . . ?
C26 C24 C25 106.6(2) . . ?
C26 C24 C16 111.6(3) . . ?
C25 C24 C16 110.5(3) . . ?
C26 C24 C27 107.6(3) . . ?
C25 C24 C27 110.3(3) . . ?
C16 C24 C27 110.1(2) . . ?
C6 C5 C4 120.9(3) . . ?
C5 C6 C7 122.2(3) . . ?
C9 C8 C7 121.5(3) . . ?
C11 C10 C9 120.4(4) . . ?
C8 C9 C10 119.9(3) . . ?
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 C18 1.376(3) . ?
O1 C17 1.383(3) . ?
N1 C1 1.312(3) . ?
N1 C13 1.377(3) . ?
C23 C18 1.386(4) . ?
C23 C22 1.395(4) . ?
C23 C1 1.460(3) . ?
C1 C2 1.424(4) . ?
C2 C3 1.406(3) . ?
C2 C17 1.411(4) . ?
C3 C14 1.396(4) . ?
C3 C4 1.444(4) . ?
C17 C16 1.388(4) . ?
C4 C13 1.393(4) . ?
C4 C5 1.423(3) . ?
C18 C19 1.382(4) . ?
C16 C15 1.399(4) . ?
C16 C24 1.536(4) . ?
C13 C12 1.444(4) . ?
C22 C21 1.381(3) . ?
C19 C20 1.374(4) . ?
C11 C10 1.374(4) . ?
C11 C12 1.403(4) . ?
C12 C7 1.412(4) . ?
C15 C14 1.370(4) . ?
C20 C21 1.378(4) . ?
C7 C8 1.407(4) . ?
C7 C6 1.413(4) . ?
C24 C26 1.533(4) . ?
C24 C25 1.536(4) . ?
C24 C27 1.541(4) . ?
C5 C6 1.346(4) . ?
C8 C9 1.358(5) . ?
C10 C9 1.396(4) . ?
