##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2019/3'
_journal_date_recd_electronic     2024-04-03
_journal_date_accepted     2024-04-19
_journal_name_full     'IUCrData'
_journal_year     2024
_journal_volume     9
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314624003572
_journal_coeditor_code     OI4001
_publ_contact_author_name     'Mamoun Bader'
_publ_contact_author_address
;
Alfaisal University
Riyadh. Saudi Arabia
;
_publ_contact_author_email     'mbader@alfaisal.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Benzo[a][1,4]benzothiazino[3,2-c]phenothiazine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bader, Mamoun M.' .
;
Department of Chemistry, Alfaisal
University, Riyadh 15333, Saudi Arabia
;
    'Pham, Phuong-Truc T.' .
;
Penn State Scranton,
Dunmore, Pennsylvania 18512
USA
;
    'Abu Khodair, Salma S.' .
;
Alfasial University, Riyadh,
Saudi Arabia
;
    'Saleh, Maysoon I.' .
;
Department of Chemistry
The University of Jordan
Amman,
Jordan
;
_publ_section_synopsis
;
The title compound crystallizes in space group P2₁/c with four
molecules in the asymmetric unit.
;
_chemical_name_systematic
;
Benzo[a][1,4]benzothiazino[3,2-c]phenothiazine
;
_chemical_name_common     24047z
_chemical_formula_moiety     'C22 H12 N2 S2'
_chemical_formula_sum     'C22 H12 N2 S2'
_chemical_formula_iupac     'C22 H12 N2 S2'
_chemical_formula_weight     368.46
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.7365(5)
_cell_length_b     3.8149(2)
_cell_length_c     35.7260(15)
_cell_angle_alpha     90
_cell_angle_beta     97.669(2)
_cell_angle_gamma     90
_cell_volume     1585.27(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2950
_cell_measurement_theta_min     2.30
_cell_measurement_theta_max     28.33
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.060
_exptl_crystal_size_min     0.010
_exptl_crystal_density_diffrn     1.544
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu     0.344
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.6419
_exptl_absorpt_correction_T_max     0.7461
_exptl_special_details     'Prof. M. Bader/ Prof. D. Alvacado / A. Bradley'
_diffrn_ambient_temperature     100(2)
_diffrn_source     'micro-focus'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker PHOTON-III CPAD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13015
_diffrn_reflns_av_R_equivalents     0.0354
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_theta_min     1.962
_diffrn_reflns_theta_max     28.341
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -3
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -47
_diffrn_reflns_limit_l_max     43
_refine_special_details     ?
_reflns_number_total     3927
_reflns_number_gt     3341
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0564
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1111
_refine_ls_wR_factor_ref     0.1163
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     3927
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0466P)²+2.0952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.517
_refine_diff_density_min     -0.560
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX4 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.54183(4) 0.21127(14) 0.30740(2) 0.01608(13) Uani d 1 . .
    S S2 0.33242(4) 0.20563(14) 0.34472(2) 0.01608(13) Uani d 1 . .
    C C1 0.55313(16) 0.3928(5) 0.35287(5) 0.0133(4) Uani d 1 . .
    C C2 0.66054(16) 0.5414(5) 0.37063(5) 0.0136(4) Uani d 1 . .
    C C3 0.66375(16) 0.6660(5) 0.40993(5) 0.0130(4) Uani d 1 . .
    C C4 0.76638(17) 0.7994(6) 0.42939(6) 0.0161(4) Uani d 1 . .
    H H4 0.833194 0.811698 0.417086 0.019 Uiso calc 1 . .
    C C5 0.77115(17) 0.9132(6) 0.46631(6) 0.0173(4) Uani d 1 . .
    H H5 0.841216 1.001428 0.479273 0.021 Uiso calc 1 . .
    C C6 0.67283(17) 0.8986(6) 0.48468(6) 0.0171(4) Uani d 1 . .
    H H6 0.676060 0.977146 0.510033 0.021 Uiso calc 1 . .
    C C7 0.57106(17) 0.7691(5) 0.46564(6) 0.0158(4) Uani d 1 . .
    H H7 0.504467 0.759988 0.478081 0.019 Uiso calc 1 . .
    C C8 0.56486(16) 0.6513(5) 0.42822(5) 0.0139(4) Uani d 1 . .
    C C9 0.45459(16) 0.5176(5) 0.40854(5) 0.0136(4) Uani d 1 . .
    C C10 0.45630(16) 0.3844(5) 0.37040(5) 0.0131(4) Uani d 1 . .
    N N1 0.75471(14) 0.5822(5) 0.35518(5) 0.0152(3) Uani d 1 . .
    C C11 0.76197(17) 0.4805(5) 0.31800(6) 0.0149(4) Uani d 1 . .
    C C12 0.86667(17) 0.5499(6) 0.30445(6) 0.0174(4) Uani d 1 . .
    H H12 0.926848 0.662186 0.320482 0.021 Uiso calc 1 . .
    C C13 0.88363(19) 0.4577(6) 0.26821(6) 0.0204(4) Uani d 1 . .
    H H13 0.955212 0.505662 0.259611 0.025 Uiso calc 1 . .
    C C14 0.79652(19) 0.2954(6) 0.24432(6) 0.0215(5) Uani d 1 . .
    H H14 0.808693 0.231235 0.219467 0.026 Uiso calc 1 . .
    C C15 0.69185(19) 0.2267(6) 0.25667(6) 0.0186(4) Uani d 1 . .
    H H15 0.632088 0.117180 0.240201 0.022 Uiso calc 1 . .
    C C16 0.67390(17) 0.3185(5) 0.29338(6) 0.0158(4) Uani d 1 . .
    N N2 0.36590(14) 0.5329(5) 0.42687(5) 0.0157(4) Uani d 1 . .
    C C17 0.25691(17) 0.4184(6) 0.41125(6) 0.0160(4) Uani d 1 . .
    C C18 0.16828(17) 0.4541(6) 0.43387(6) 0.0178(4) Uani d 1 . .
    H H18 0.185008 0.553665 0.458358 0.021 Uiso calc 1 . .
    C C19 0.05728(17) 0.3472(6) 0.42117(6) 0.0197(4) Uani d 1 . .
    H H19 -0.001115 0.371277 0.437018 0.024 Uiso calc 1 . .
    C C20 0.03085(18) 0.2041(6) 0.38515(6) 0.0210(4) Uani d 1 . .
    H H20 -0.045527 0.132118 0.376360 0.025 Uiso calc 1 . .
    C C21 0.11667(17) 0.1672(6) 0.36219(6) 0.0182(4) Uani d 1 . .
    H H21 0.098693 0.071365 0.337562 0.022 Uiso calc 1 . .
    C C22 0.22938(17) 0.2703(5) 0.37509(6) 0.0155(4) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C16 . 1.740(2) ?
    S1 C1 . 1.755(2) ?
    S2 C22 . 1.747(2) ?
    S2 C10 . 1.751(2) ?
    C1 C10 . 1.369(3) ?
    C1 C2 . 1.449(3) ?
    C2 N1 . 1.309(2) ?
    C2 C3 . 1.478(3) ?
    C3 C4 . 1.404(3) ?
    C3 C8 . 1.407(3) ?
    C4 C5 . 1.382(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.403(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.384(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.403(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.479(3) ?
    C9 N2 . 1.303(2) ?
    C9 C10 . 1.457(3) ?
    N1 C11 . 1.398(3) ?
    C11 C12 . 1.405(3) ?
    C11 C16 . 1.407(3) ?
    C12 C13 . 1.382(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.387(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.385(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.400(3) ?
    C15 H15 . 0.9500 ?
    N2 C17 . 1.396(3) ?
    C17 C18 . 1.406(3) ?
    C17 C22 . 1.407(3) ?
    C18 C19 . 1.383(3) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.394(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.389(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.398(3) ?
    C21 H21 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C16 S1 C1 . . 102.32(10) ?
    C22 S2 C10 . . 102.41(10) ?
    C10 C1 C2 . . 122.38(18) ?
    C10 C1 S1 . . 116.71(15) ?
    C2 C1 S1 . . 120.91(14) ?
    N1 C2 C1 . . 126.58(18) ?
    N1 C2 C3 . . 116.52(17) ?
    C1 C2 C3 . . 116.89(16) ?
    C4 C3 C8 . . 119.40(18) ?
    C4 C3 C2 . . 119.92(17) ?
    C8 C3 C2 . . 120.68(17) ?
    C5 C4 C3 . . 120.62(18) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 120.19(19) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C7 C6 C5 . . 119.59(19) ?
    C7 C6 H6 . . 120.2 ?
    C5 C6 H6 . . 120.2 ?
    C6 C7 C8 . . 120.95(18) ?
    C6 C7 H7 . . 119.5 ?
    C8 C7 H7 . . 119.5 ?
    C7 C8 C3 . . 119.24(18) ?
    C7 C8 C9 . . 119.63(17) ?
    C3 C8 C9 . . 121.12(17) ?
    N2 C9 C10 . . 126.69(18) ?
    N2 C9 C8 . . 116.92(17) ?
    C10 C9 C8 . . 116.40(16) ?
    C1 C10 C9 . . 122.38(17) ?
    C1 C10 S2 . . 116.83(15) ?
    C9 C10 S2 . . 120.79(14) ?
    C2 N1 C11 . . 122.00(17) ?
    N1 C11 C12 . . 116.25(18) ?
    N1 C11 C16 . . 125.67(18) ?
    C12 C11 C16 . . 118.08(18) ?
    C13 C12 C11 . . 121.1(2) ?
    C13 C12 H12 . . 119.4 ?
    C11 C12 H12 . . 119.4 ?
    C12 C13 C14 . . 120.25(19) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 120.1(2) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 120.1(2) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C11 . . 120.35(19) ?
    C15 C16 S1 . . 117.50(16) ?
    C11 C16 S1 . . 122.11(15) ?
    C9 N2 C17 . . 122.41(17) ?
    N2 C17 C18 . . 116.65(18) ?
    N2 C17 C22 . . 125.35(18) ?
    C18 C17 C22 . . 118.00(18) ?
    C19 C18 C17 . . 121.3(2) ?
    C19 C18 H18 . . 119.3 ?
    C17 C18 H18 . . 119.3 ?
    C18 C19 C20 . . 120.15(19) ?
    C18 C19 H19 . . 119.9 ?
    C20 C19 H19 . . 119.9 ?
    C21 C20 C19 . . 119.70(19) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C20 C21 C22 . . 120.4(2) ?
    C20 C21 H21 . . 119.8 ?
    C22 C21 H21 . . 119.8 ?
    C21 C22 C17 . . 120.46(18) ?
    C21 C22 S2 . . 117.29(16) ?
    C17 C22 S2 . . 122.25(15) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C16 S1 C1 C10 . . . . 173.32(16) ?
    C16 S1 C1 C2 . . . . -7.01(19) ?
    C10 C1 C2 N1 . . . . -175.1(2) ?
    S1 C1 C2 N1 . . . . 5.3(3) ?
    C10 C1 C2 C3 . . . . 3.7(3) ?
    S1 C1 C2 C3 . . . . -175.95(14) ?
    N1 C2 C3 C4 . . . . -3.8(3) ?
    C1 C2 C3 C4 . . . . 177.34(18) ?
    N1 C2 C3 C8 . . . . 176.48(19) ?
    C1 C2 C3 C8 . . . . -2.4(3) ?
    C8 C3 C4 C5 . . . . 0.5(3) ?
    C2 C3 C4 C5 . . . . -179.23(19) ?
    C3 C4 C5 C6 . . . . -0.5(3) ?
    C4 C5 C6 C7 . . . . 0.1(3) ?
    C5 C6 C7 C8 . . . . 0.2(3) ?
    C6 C7 C8 C3 . . . . -0.1(3) ?
    C6 C7 C8 C9 . . . . -179.42(19) ?
    C4 C3 C8 C7 . . . . -0.2(3) ?
    C2 C3 C8 C7 . . . . 179.50(18) ?
    C4 C3 C8 C9 . . . . 179.07(19) ?
    C2 C3 C8 C9 . . . . -1.2(3) ?
    C7 C8 C9 N2 . . . . 3.3(3) ?
    C3 C8 C9 N2 . . . . -176.02(19) ?
    C7 C8 C9 C10 . . . . -177.15(18) ?
    C3 C8 C9 C10 . . . . 3.5(3) ?
    C2 C1 C10 C9 . . . . -1.3(3) ?
    S1 C1 C10 C9 . . . . 178.35(15) ?
    C2 C1 C10 S2 . . . . 178.49(15) ?
    S1 C1 C10 S2 . . . . -1.8(2) ?
    N2 C9 C10 C1 . . . . 177.2(2) ?
    C8 C9 C10 C1 . . . . -2.3(3) ?
    N2 C9 C10 S2 . . . . -2.6(3) ?
    C8 C9 C10 S2 . . . . 177.87(14) ?
    C22 S2 C10 C1 . . . . -176.21(16) ?
    C22 S2 C10 C9 . . . . 3.60(18) ?
    C1 C2 N1 C11 . . . . -0.2(3) ?
    C3 C2 N1 C11 . . . . -178.92(17) ?
    C2 N1 C11 C12 . . . . 177.87(19) ?
    C2 N1 C11 C16 . . . . -1.7(3) ?
    N1 C11 C12 C13 . . . . 179.44(19) ?
    C16 C11 C12 C13 . . . . -0.9(3) ?
    C11 C12 C13 C14 . . . . 0.4(3) ?
    C12 C13 C14 C15 . . . . 0.4(3) ?
    C13 C14 C15 C16 . . . . -0.5(3) ?
    C14 C15 C16 C11 . . . . -0.1(3) ?
    C14 C15 C16 S1 . . . . -177.97(17) ?
    N1 C11 C16 C15 . . . . -179.62(19) ?
    C12 C11 C16 C15 . . . . 0.8(3) ?
    N1 C11 C16 S1 . . . . -1.9(3) ?
    C12 C11 C16 S1 . . . . 178.56(16) ?
    C1 S1 C16 C15 . . . . -176.64(16) ?
    C1 S1 C16 C11 . . . . 5.5(2) ?
    C10 C9 N2 C17 . . . . -0.2(3) ?
    C8 C9 N2 C17 . . . . 179.35(18) ?
    C9 N2 C17 C18 . . . . -179.1(2) ?
    C9 N2 C17 C22 . . . . 1.2(3) ?
    N2 C17 C18 C19 . . . . -179.7(2) ?
    C22 C17 C18 C19 . . . . 0.1(3) ?
    C17 C18 C19 C20 . . . . -0.7(3) ?
    C18 C19 C20 C21 . . . . 0.4(3) ?
    C19 C20 C21 C22 . . . . 0.5(3) ?
    C20 C21 C22 C17 . . . . -1.1(3) ?
    C20 C21 C22 S2 . . . . 178.64(17) ?
    N2 C17 C22 C21 . . . . -179.5(2) ?
    C18 C17 C22 C21 . . . . 0.8(3) ?
    N2 C17 C22 S2 . . . . 0.8(3) ?
    C18 C17 C22 S2 . . . . -178.90(16) ?
    C10 S2 C22 C21 . . . . 177.42(17) ?
    C10 S2 C22 C17 . . . . -2.8(2) ?
_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     0.919
_shelx_estimated_absorpt_T_max     0.997
