#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/09/2230946.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230946
loop_
_publ_author_name
'Siddegowda, M. S.'
'Jasinski, Jerry P.'
'Golen, James A.'
'Yathirajan, H. S.'
_publ_section_title
;
 1-(5,5-Dioxido-10H-phenothiazin-10-yl)ethanone
;
_journal_coeditor_code           YK2011
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1702
_journal_paper_doi               10.1107/S1600536811021854
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H11 N O3 S'
_chemical_formula_moiety         'C14 H11 N O3 S'
_chemical_formula_sum            'C14 H11 N O3 S'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
1-(5,5-Dioxido-10H-phenothiazin-10-yl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.142(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5715(6)
_cell_length_b                   8.7648(4)
_cell_length_c                   11.5828(5)
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.34
_cell_measurement_theta_min      3.30
_cell_volume                     1275.38(10)
_computing_cell_refinement
'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlisPRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5342
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.3216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2263
_reflns_number_total             2597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            yk2011.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230946
_cod_database_fobs_code          2230946
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.27860(3) 0.53431(4) 0.88913(3) 0.03458(15) Uani d . 1 1 . .
O O1 0.18673(10) 0.57759(15) 0.95043(10) 0.0481(3) Uani d . 1 1 . .
O O2 0.34587(11) 0.41839(15) 0.93886(12) 0.0552(4) Uani d . 1 1 . .
O O3 0.14803(10) 0.98466(14) 0.75069(12) 0.0492(3) Uani d . 1 1 . .
N N1 0.22033(10) 0.75636(14) 0.71011(11) 0.0301(3) Uani d . 1 1 . .
C C1 0.35385(12) 0.69784(18) 0.86054(13) 0.0330(3) Uani d . 1 1 . .
C C2 0.44865(13) 0.7260(2) 0.92270(15) 0.0441(4) Uani d . 1 1 . .
H H2B 0.4745 0.6564 0.9801 0.053 Uiso calc R 1 1 . .
C C3 0.50395(14) 0.8569(2) 0.89904(17) 0.0521(5) Uani d . 1 1 . .
H H3A 0.5685 0.8793 0.9410 0.063 Uiso calc R 1 1 . .
C C4 0.46595(15) 0.9559(2) 0.81450(18) 0.0523(5) Uani d . 1 1 . .
H H4A 0.5045 1.0467 0.7999 0.063 Uiso calc R 1 1 . .
C C5 0.37288(14) 0.9262(2) 0.75021(15) 0.0415(4) Uani d . 1 1 . .
H H5A 0.3487 0.9941 0.6909 0.050 Uiso calc R 1 1 . .
C C6 0.31596(11) 0.79526(17) 0.77439(13) 0.0307(3) Uani d . 1 1 . .
C C7 0.21083(11) 0.60193(17) 0.67173(13) 0.0303(3) Uani d . 1 1 . .
C C8 0.18008(14) 0.5650(2) 0.55873(15) 0.0413(4) Uani d . 1 1 . .
H H8A 0.1651 0.6434 0.5038 0.050 Uiso calc R 1 1 . .
C C9 0.17142(16) 0.4131(2) 0.52666(16) 0.0486(5) Uani d . 1 1 . .
H H9A 0.1488 0.3881 0.4498 0.058 Uiso calc R 1 1 . .
C C10 0.19506(15) 0.2974(2) 0.60424(16) 0.0470(4) Uani d . 1 1 . .
H H10A 0.1866 0.1939 0.5814 0.056 Uiso calc R 1 1 . .
C C11 0.23104(13) 0.33228(18) 0.71510(15) 0.0388(4) Uani d . 1 1 . .
H H11A 0.2510 0.2536 0.7680 0.047 Uiso calc R 1 1 . .
C C12 0.23754(12) 0.48386(17) 0.74801(13) 0.0301(3) Uani d . 1 1 . .
C C13 0.13555(12) 0.85896(18) 0.70914(14) 0.0355(4) Uani d . 1 1 . .
C C14 0.03011(14) 0.8073(2) 0.65925(19) 0.0527(5) Uani d . 1 1 . .
H H14A -0.0254 0.8789 0.6816 0.079 Uiso calc R 1 1 . .
H H14B 0.0140 0.7054 0.6886 0.079 Uiso calc R 1 1 . .
H H14C 0.0326 0.8039 0.5748 0.079 Uiso calc R 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 117.73(8) ?
O2 S1 C12 . . 110.23(8) ?
O1 S1 C12 . . 108.36(7) ?
O2 S1 C1 . . 109.97(8) ?
O1 S1 C1 . . 109.16(7) ?
C12 S1 C1 . . 99.91(7) ?
C13 N1 C7 . . 123.62(12) ?
C13 N1 C6 . . 118.52(13) ?
C7 N1 C6 . . 116.52(12) ?
C6 C1 C2 . . 121.92(15) ?
C6 C1 S1 . . 117.79(11) ?
C2 C1 S1 . . 120.29(13) ?
C3 C2 C1 . . 118.35(17) ?
C3 C2 H2B . . 120.8 ?
C1 C2 H2B . . 120.8 ?
C2 C3 C4 . . 120.13(17) ?
C2 C3 H3A . . 119.9 ?
C4 C3 H3A . . 119.9 ?
C3 C4 C5 . . 121.69(17) ?
C3 C4 H4A . . 119.2 ?
C5 C4 H4A . . 119.2 ?
C6 C5 C4 . . 118.54(17) ?
C6 C5 H5A . . 120.7 ?
C4 C5 H5A . . 120.7 ?
C1 C6 C5 . . 119.33(14) ?
C1 C6 N1 . . 119.19(13) ?
C5 C6 N1 . . 121.45(14) ?
C8 C7 C12 . . 118.45(14) ?
C8 C7 N1 . . 122.08(14) ?
C12 C7 N1 . . 119.41(13) ?
C9 C8 C7 . . 119.52(16) ?
C9 C8 H8A . . 120.2 ?
C7 C8 H8A . . 120.2 ?
C10 C9 C8 . . 121.26(16) ?
C10 C9 H9A . . 119.4 ?
C8 C9 H9A . . 119.4 ?
C11 C10 C9 . . 119.88(16) ?
C11 C10 H10A . . 120.1 ?
C9 C10 H10A . . 120.1 ?
C10 C11 C12 . . 118.89(16) ?
C10 C11 H11A . . 120.6 ?
C12 C11 H11A . . 120.6 ?
C11 C12 C7 . . 121.87(15) ?
C11 C12 S1 . . 120.77(12) ?
C7 C12 S1 . . 117.36(11) ?
O3 C13 N1 . . 119.75(15) ?
O3 C13 C14 . . 121.93(15) ?
N1 C13 C14 . . 118.29(14) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 O2 . 1.4292(13) ?
S1 O1 . 1.4294(13) ?
S1 C12 . 1.7524(16) ?
S1 C1 . 1.7557(16) ?
O3 C13 . 1.210(2) ?
N1 C13 . 1.394(2) ?
N1 C7 . 1.4283(19) ?
N1 C6 . 1.4314(19) ?
C1 C6 . 1.384(2) ?
C1 C2 . 1.391(2) ?
C2 C3 . 1.374(3) ?
C2 H2B . 0.9500 ?
C3 C4 . 1.380(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.388(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.387(2) ?
C5 H5A . 0.9500 ?
C7 C8 . 1.389(2) ?
C7 C12 . 1.394(2) ?
C8 C9 . 1.386(2) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.380(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.380(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.384(2) ?
C11 H11A . 0.9500 ?
C13 C14 . 1.496(2) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2B O2 3_667 0.95 2.50 3.246(2) 135
C8 H8A O1 4_575 0.95 2.54 3.376(2) 147
C9 H9A O3 4_575 0.95 2.56 3.322(2) 137
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
O2 S1 C1 C6 . . . . 154.78(12) ?
O1 S1 C1 C6 . . . . -74.65(14) ?
C12 S1 C1 C6 . . . . 38.88(13) ?
O2 S1 C1 C2 . . . . -24.71(16) ?
O1 S1 C1 C2 . . . . 105.85(14) ?
C12 S1 C1 C2 . . . . -140.62(14) ?
C6 C1 C2 C3 . . . . 1.8(3) ?
S1 C1 C2 C3 . . . . -178.75(14) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . -1.0(3) ?
C3 C4 C5 C6 . . . . 1.7(3) ?
C2 C1 C6 C5 . . . . -1.1(2) ?
S1 C1 C6 C5 . . . . 179.43(12) ?
C2 C1 C6 N1 . . . . 177.23(14) ?
S1 C1 C6 N1 . . . . -2.26(19) ?
C4 C5 C6 C1 . . . . -0.6(2) ?
C4 C5 C6 N1 . . . . -178.90(15) ?
C13 N1 C6 C1 . . . . 122.59(15) ?
C7 N1 C6 C1 . . . . -44.68(19) ?
C13 N1 C6 C5 . . . . -59.1(2) ?
C7 N1 C6 C5 . . . . 133.59(15) ?
C13 N1 C7 C8 . . . . 61.5(2) ?
C6 N1 C7 C8 . . . . -131.99(15) ?
C13 N1 C7 C12 . . . . -121.42(16) ?
C6 N1 C7 C12 . . . . 45.13(19) ?
C12 C7 C8 C9 . . . . 3.4(2) ?
N1 C7 C8 C9 . . . . -179.49(16) ?
C7 C8 C9 C10 . . . . -1.5(3) ?
C8 C9 C10 C11 . . . . -1.9(3) ?
C9 C10 C11 C12 . . . . 3.3(3) ?
C10 C11 C12 C7 . . . . -1.3(2) ?
C10 C11 C12 S1 . . . . 177.93(13) ?
C8 C7 C12 C11 . . . . -2.0(2) ?
N1 C7 C12 C11 . . . . -179.24(14) ?
C8 C7 C12 S1 . . . . 178.73(12) ?
N1 C7 C12 S1 . . . . 1.50(18) ?
O2 S1 C12 C11 . . . . 26.68(16) ?
O1 S1 C12 C11 . . . . -103.47(14) ?
C1 S1 C12 C11 . . . . 142.39(13) ?
O2 S1 C12 C7 . . . . -154.06(12) ?
O1 S1 C12 C7 . . . . 75.79(13) ?
C1 S1 C12 C7 . . . . -38.35(13) ?
C7 N1 C13 O3 . . . . 174.72(15) ?
C6 N1 C13 O3 . . . . 8.4(2) ?
C7 N1 C13 C14 . . . . -3.5(2) ?
C6 N1 C13 C14 . . . . -169.76(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 306629
