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#$Date: 2023-06-05 07:57:56 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284336 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159361.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_7159361
loop_
_publ_author_name
'Ammon, Erich'
'Heine, Paul'
'Cordero, Miguel Andre Argüello'
'Lochbrunner, Stefan'
'Villinger, Alexander'
'Ehlers, Peter'
'Langer, Peter'
_publ_section_title
;
 Dibenzoacridines: synthesis by alkyne-carbonyl-metathesis and properties.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4504
_journal_page_last               4517
_journal_paper_doi               10.1039/d3ob00407d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C31 H17 N O2 S2'
_chemical_formula_sum            'C31 H17 N O2 S2'
_chemical_formula_weight         499.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-02 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.440(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.245(4)
_cell_length_b                   18.740(5)
_cell_length_c                   8.084(2)
_cell_measurement_reflns_used    3944
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.92
_cell_measurement_theta_min      3.29
_cell_volume                     2271.3(10)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21882
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.998
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0616P)²+1.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00407d2.cif
_cod_data_source_block           is_erp126
_cod_depositor_comments
'Adding full bibliography for 7159361--7159362.cif.'
_cod_original_cell_volume        2271.3(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7159361
_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.
;
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.56458(9) 0.38773(7) 0.69358(16) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.63332(9) 0.34706(7) 0.63432(17) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.70285(10) 0.38129(7) 0.58272(17) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.7482 0.3545 0.5444 0.024 Uiso 1 1 calc R U . . .
C4 C 0.70719(9) 0.45684(7) 0.58654(17) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.74041(10) 0.58549(8) 0.58238(19) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.7640 0.6319 0.5720 0.028 Uiso 1 1 calc R U . . .
C6 C 0.66306(9) 0.57300(7) 0.63758(18) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.6265 0.6095 0.6702 0.025 Uiso 1 1 calc R U . . .
C7 C 0.64270(9) 0.49873(7) 0.64125(17) 0.0170(2) Uani 1 1 d . . . . .
C8 C 0.56839(9) 0.46418(7) 0.69513(16) 0.0162(2) Uani 1 1 d . . . . .
C9 C 0.5000 0.50106(9) 0.7500 0.0166(3) Uani 1 2 d S T P . .
H9 H 0.5000 0.5518 0.7500 0.020 Uiso 1 2 calc R U P . .
C10 C 0.63556(10) 0.26679(7) 0.63463(18) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.55723(9) 0.22423(7) 0.55466(18) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.48342(11) 0.25472(8) 0.45388(19) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.4805 0.3051 0.4404 0.029 Uiso 1 1 calc R U . . .
C13 C 0.41389(11) 0.21276(9) 0.3726(2) 0.0279(3) Uani 1 1 d . . . . .
H13 H 0.3632 0.2341 0.3052 0.033 Uiso 1 1 calc R U . . .
C14 C 0.41911(12) 0.13955(9) 0.3907(3) 0.0368(4) Uani 1 1 d . . . . .
H14 H 0.3724 0.1103 0.3335 0.044 Uiso 1 1 calc R U . . .
C15 C 0.49190(13) 0.10870(10) 0.4915(3) 0.0488(6) Uani 1 1 d . . . . .
H15 H 0.4945 0.0583 0.5047 0.059 Uiso 1 1 calc R U . . .
C16 C 0.56093(11) 0.15043(8) 0.5732(2) 0.0316(4) Uani 1 1 d . . . . .
H16 H 0.6110 0.1288 0.6421 0.038 Uiso 1 1 calc R U . . .
N1 N 0.5000 0.35145(8) 0.7500 0.0174(3) Uani 1 2 d S T P . .
O1 O 0.70575(8) 0.23708(6) 0.69226(17) 0.0345(3) Uani 1 1 d . . . . .
S1 S 0.79141(2) 0.50842(2) 0.53307(5) 0.02193(11) 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'
S S 0.1246 0.1234 '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
N1 C1 C8 122.28(13) . . ?
N1 C1 C2 117.76(12) . . ?
C8 C1 C2 119.94(12) . . ?
C3 C2 C1 120.15(12) . . ?
C3 C2 C10 116.81(12) . . ?
C1 C2 C10 122.96(12) . . ?
C2 C3 C4 119.85(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C4 C3 122.53(12) . . ?
C7 C4 S1 111.38(10) . . ?
C3 C4 S1 126.06(11) . . ?
C6 C5 S1 112.83(11) . . ?
C6 C5 H5 123.6 . . ?
S1 C5 H5 123.6 . . ?
C5 C6 C7 112.38(13) . . ?
C5 C6 H6 123.8 . . ?
C7 C6 H6 123.8 . . ?
C4 C7 C6 112.01(12) . . ?
C4 C7 C8 118.86(12) . . ?
C6 C7 C8 129.12(12) . . ?
C9 C8 C1 117.94(13) . . ?
C9 C8 C7 123.40(12) . . ?
C1 C8 C7 118.66(12) . . ?
C8 C9 C8 120.31(17) 2_656 . ?
C8 C9 H9 119.8 2_656 . ?
C8 C9 H9 119.8 . . ?
O1 C10 C11 120.12(13) . . ?
O1 C10 C2 118.31(13) . . ?
C11 C10 C2 121.37(12) . . ?
C12 C11 C16 119.05(14) . . ?
C12 C11 C10 122.53(13) . . ?
C16 C11 C10 118.29(13) . . ?
C13 C12 C11 120.92(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.29(16) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 120.26(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.50(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.97(16) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C1 N1 C1 119.15(16) . 2_656 ?
C5 S1 C4 91.39(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
C1 N1 1.3425(16) . ?
C1 C8 1.4338(18) . ?
C1 C2 1.4459(19) . ?
C2 C3 1.367(2) . ?
C2 C10 1.5046(19) . ?
C3 C4 1.4173(19) . ?
C3 H3 0.9500 . ?
C4 C7 1.3914(19) . ?
C4 S1 1.7237(14) . ?
C5 C6 1.355(2) . ?
C5 S1 1.7210(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4276(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4392(19) . ?
C8 C9 1.3889(16) . ?
C9 C8 1.3889(16) 2_656 ?
C9 H9 0.9500 . ?
C10 O1 1.2213(17) . ?
C10 C11 1.483(2) . ?
C11 C12 1.387(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N1 C1 1.3426(16) 2_656 ?
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
N1 C1 C2 C3 -177.01(11) . . . . ?
C8 C1 C2 C3 1.23(19) . . . . ?
N1 C1 C2 C10 -0.44(19) . . . . ?
C8 C1 C2 C10 177.80(12) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C10 C2 C3 C4 -177.13(13) . . . . ?
C2 C3 C4 C7 -0.1(2) . . . . ?
C2 C3 C4 S1 177.71(11) . . . . ?
S1 C5 C6 C7 -0.03(17) . . . . ?
C3 C4 C7 C6 178.44(13) . . . . ?
S1 C4 C7 C6 0.37(15) . . . . ?
C3 C4 C7 C8 -0.4(2) . . . . ?
S1 C4 C7 C8 -178.46(10) . . . . ?
C5 C6 C7 C4 -0.22(18) . . . . ?
C5 C6 C7 C8 178.46(13) . . . . ?
N1 C1 C8 C9 -3.08(18) . . . . ?
C2 C1 C8 C9 178.76(10) . . . . ?
N1 C1 C8 C7 176.50(10) . . . . ?
C2 C1 C8 C7 -1.66(19) . . . . ?
C4 C7 C8 C9 -179.20(11) . . . . ?
C6 C7 C8 C9 2.2(2) . . . . ?
C4 C7 C8 C1 1.25(19) . . . . ?
C6 C7 C8 C1 -177.36(13) . . . . ?
C1 C8 C9 C8 1.44(8) . . . 2_656 ?
C7 C8 C9 C8 -178.12(14) . . . 2_656 ?
C3 C2 C10 O1 44.76(19) . . . . ?
C1 C2 C10 O1 -131.92(15) . . . . ?
C3 C2 C10 C11 -130.21(14) . . . . ?
C1 C2 C10 C11 53.11(19) . . . . ?
O1 C10 C11 C12 -164.71(15) . . . . ?
C2 C10 C11 C12 10.2(2) . . . . ?
O1 C10 C11 C16 11.0(2) . . . . ?
C2 C10 C11 C16 -174.09(14) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C13 175.89(14) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C10 C11 C16 C15 -175.71(17) . . . . ?
C8 C1 N1 C1 1.56(9) . . . 2_656 ?
C2 C1 N1 C1 179.76(13) . . . 2_656 ?
C6 C5 S1 C4 0.21(12) . . . . ?
C7 C4 S1 C5 -0.33(11) . . . . ?
C3 C4 S1 C5 -178.31(13) . . . . ?
