#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:23:20 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235073 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/35/1553502.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_1553502
loop_
_publ_author_name
'Zagranyarski, Yulian'
'Skabeev, Artem'
'Ma, Yingjie'
'Müllen, Klaus'
'Li, Chen'
_publ_section_title
;
 Facile synthesis of annulated heterocyclic benzo[kl]acridine derivatives
 via one-pot N--H/C--H coupling
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1520
_journal_paper_doi               10.1039/C6QO00371K
_journal_volume                  3
_journal_year                    2016
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C22 H13 N S'
_chemical_formula_sum            'C22 H13 N S'
_chemical_formula_weight         323.39
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   ' ?'
_atom_sites_solution_primary     ' ?'
_atom_sites_solution_secondary   ' ?'
_audit_update_record
;
2016-07-19 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3471(9)
_cell_length_b                   11.2916(8)
_cell_length_c                   8.0242(4)
_cell_measurement_temperature    193
_cell_volume                     1481.15(15)
_computing_publication_material  'PLATON (Spek, 2003)'
_diffrn_detector_area_resol_mean 18.4
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_reduction_process
;
;
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   ' ?'
_exptl_crystal_colour            ' ?'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       ' ?'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_extinction_method     ' ?'
_refine_ls_hydrogen_treatment    ' ?'
_refine_ls_number_restraints     0
_refine_ls_weighting_scheme      ?
_cod_data_source_file            c6qo00371k2.cif
_cod_data_source_block           bqpt
_cod_database_code               1553502
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+x,-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
S16 S Uani 0.46146 0.00626 -0.02125 1.000 0.0307
N1 N Uani 0.32799 0.12714 0.16712 1.000 0.0243
C2 C Uani 0.25477 0.19197 0.19773 1.000 0.0237
C3 C Uani 0.18032 0.14882 0.14718 1.000 0.0276
C4 C Uani 0.10811 0.20836 0.19153 1.000 0.0314
C5 C Uani 0.10997 0.31020 0.28194 1.000 0.0319
C6 C Uani 0.18584 0.36034 0.32952 1.000 0.0279
C7 C Uani 0.19154 0.46681 0.42119 1.000 0.0325
C8 C Uani 0.26581 0.51250 0.46537 1.000 0.0346
C9 C Uani 0.33813 0.45671 0.41483 1.000 0.0312
C10 C Uani 0.33678 0.35421 0.32247 1.000 0.0259
C11 C Uani 0.41007 0.29737 0.25325 1.000 0.0259
C12 C Uani 0.48678 0.35358 0.25436 1.000 0.0339
C13 C Uani 0.55521 0.30060 0.18423 1.000 0.0367
C14 C Uani 0.54765 0.19207 0.10611 1.000 0.0325
C15 C Uani 0.47243 0.13634 0.09790 1.000 0.0275
C17 C Uani 0.38825 -0.06539 0.10523 1.000 0.0254
C18 C Uani 0.39004 -0.18813 0.12079 1.000 0.0287
C19 C Uani 0.33224 -0.24510 0.21705 1.000 0.0313
C20 C Uani 0.27384 -0.17929 0.30072 1.000 0.0302
C21 C Uani 0.27200 -0.05762 0.28684 1.000 0.0262
C22 C Uani 0.32852 0.00149 0.18630 1.000 0.0229
C23 C Uani 0.25969 0.30183 0.28286 1.000 0.0235
C24 C Uani 0.40352 0.18760 0.17338 1.000 0.0237
H3 H Uiso 0.17763 0.07862 0.08215 1.000 0.0331
H4 H Uiso 0.05686 0.17682 0.15766 1.000 0.0377
H5 H Uiso 0.06029 0.34775 0.31321 1.000 0.0383
H7 H Uiso 0.14298 0.50727 0.45261 1.000 0.0390
H8 H Uiso 0.26839 0.58253 0.53077 1.000 0.0415
H9 H Uiso 0.38927 0.49043 0.44503 1.000 0.0375
H12 H Uiso 0.49190 0.42953 0.30421 1.000 0.0407
H13 H Uiso 0.60695 0.33871 0.18988 1.000 0.0441
H14 H Uiso 0.59434 0.15558 0.05783 1.000 0.0390
H18 H Uiso 0.43107 -0.23268 0.06511 1.000 0.0344
H19 H Uiso 0.33253 -0.32900 0.22583 1.000 0.0375
H20 H Uiso 0.23458 -0.21837 0.36849 1.000 0.0362
H21 H Uiso 0.23194 -0.01362 0.34617 1.000 0.0315
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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
