#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222562.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_2222562
loop_
_publ_author_name
'Wang, Qiang'
'Yang, Lei'
'Xu, Zhouqing'
'Sun, Yanchun'
_publ_section_title
;
 10-Acetyl-10H-phenothiazine 5-oxide
;
_journal_coeditor_code           BH2235
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1978
_journal_paper_doi               10.1107/S1600536809028487
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H11 N O2 S'
_chemical_formula_moiety         'C14 H11 N O2 S'
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30
_chemical_melting_point          443
_chemical_name_systematic
;
10-Acetyl-10H-phenothiazine 5-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.9630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.12440(10)
_cell_length_b                   14.1787(2)
_cell_length_c                   10.75760(10)
_cell_measurement_reflns_used    4917
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.40
_cell_volume                     1216.59(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11538
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9672
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0458
_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)+(0.0506P)²+0.5122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                2404
_reflns_number_total             3067
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            bh2235.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222562
_cod_database_fobs_code          2222562
loop_
_symmetry_equiv_pos_as_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_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_disorder_assembly
_atom_site_disorder_group
C C1 0.2768(2) 1.03984(14) 0.34599(17) 0.0419(4) Uani d . 1 A .
C C2 0.4325(3) 1.08344(17) 0.3653(2) 0.0552(6) Uani d . 1 . .
H H2A 0.4440 1.1461 0.3911 0.066 Uiso calc R 1 . .
C C3 0.5687(3) 1.0329(2) 0.3456(2) 0.0679(7) Uani d . 1 . .
H H3A 0.6736 1.0614 0.3585 0.081 Uiso calc R 1 . .
C C4 0.5520(3) 0.9400(2) 0.3069(2) 0.0603(6) Uani d . 1 . .
H H4A 0.6461 0.9059 0.2960 0.072 Uiso calc R 1 . .
C C5 0.3958(2) 0.89724(16) 0.28427(19) 0.0482(5) Uani d . 1 . .
H H5A 0.3845 0.8353 0.2554 0.058 Uiso calc R 1 . .
C C6 0.2563(2) 0.94696(13) 0.30478(16) 0.0372(4) Uani d . 1 . .
C C7 -0.0305(2) 0.97033(13) 0.19798(17) 0.0383(4) Uani d . 1 . .
C C8 -0.0329(2) 1.06443(13) 0.23222(18) 0.0415(4) Uani d . 1 A .
C C9 -0.1414(3) 1.12817(16) 0.1596(2) 0.0552(5) Uani d . 1 . .
H H9A -0.1414 1.1914 0.1824 0.066 Uiso calc R 1 . .
C C10 -0.2486(3) 1.09580(18) 0.0533(2) 0.0600(6) Uani d . 1 . .
H H10A -0.3219 1.1375 0.0040 0.072 Uiso calc R 1 . .
C C11 -0.2480(3) 1.00256(18) 0.0197(2) 0.0580(6) Uani d . 1 . .
H H11A -0.3223 0.9815 -0.0515 0.070 Uiso calc R 1 . .
C C12 -0.1381(2) 0.93909(15) 0.09038(19) 0.0467(5) Uani d . 1 . .
H H12A -0.1369 0.8763 0.0657 0.056 Uiso calc R 1 . .
C C13 0.0405(3) 0.82363(14) 0.3156(2) 0.0479(5) Uani d . 1 . .
C C14 0.1638(3) 0.76880(16) 0.4099(2) 0.0602(6) Uani d . 1 . .
H H14A 0.1048 0.7321 0.4622 0.090 Uiso calc R 1 . .
H H14B 0.2386 0.8116 0.4619 0.090 Uiso calc R 1 . .
H H14C 0.2271 0.7276 0.3659 0.090 Uiso calc R 1 . .
N N1 0.09014(18) 0.90973(10) 0.27386(15) 0.0388(3) Uani d . 1 . .
O O2 -0.1007(2) 0.79521(12) 0.2791(2) 0.0756(6) Uani d . 1 . .
S S1 0.09806(7) 1.10145(4) 0.37655(5) 0.05019(17) Uani d D 1 . .
O O1A 0.1306(3) 1.20324(11) 0.37154(19) 0.0716(7) Uani d PD 0.886(4) A 1
O O1B 0.0214(17) 1.0640(10) 0.4755(10) 0.068(5) Uani d PD 0.114(4) A 2
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
C2 C1 C6 . . 121.40(19) ?
C2 C1 S1 . . 120.45(17) ?
C6 C1 S1 . . 118.14(14) ?
C3 C2 C1 . . 119.0(2) ?
C3 C2 H2A . . 120.5 ?
C1 C2 H2A . . 120.5 ?
C2 C3 C4 . . 120.7(2) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C3 C4 C5 . . 120.3(2) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C4 C5 C6 . . 119.9(2) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C5 C6 C1 . . 118.67(17) ?
C5 C6 N1 . . 122.65(17) ?
C1 C6 N1 . . 118.40(16) ?
C12 C7 C8 . . 119.46(17) ?
C12 C7 N1 . . 122.58(17) ?
C8 C7 N1 . . 117.90(16) ?
C7 C8 C9 . . 121.0(2) ?
C7 C8 S1 . . 118.55(14) ?
C9 C8 S1 . . 120.37(16) ?
C10 C9 C8 . . 118.8(2) ?
C10 C9 H9A . . 120.6 ?
C8 C9 H9A . . 120.6 ?
C11 C10 C9 . . 120.4(2) ?
C11 C10 H10A . . 119.8 ?
C9 C10 H10A . . 119.8 ?
C10 C11 C12 . . 121.0(2) ?
C10 C11 H11A . . 119.5 ?
C12 C11 H11A . . 119.5 ?
C7 C12 C11 . . 119.3(2) ?
C7 C12 H12A . . 120.4 ?
C11 C12 H12A . . 120.4 ?
O2 C13 N1 . . 120.32(18) ?
O2 C13 C14 . . 121.16(19) ?
N1 C13 C14 . . 118.48(18) ?
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 ?
C13 N1 C6 . . 124.75(15) ?
C13 N1 C7 . . 120.12(15) ?
C6 N1 C7 . . 115.08(14) ?
O1B S1 O1A . . 119.8(6) ?
O1B S1 C1 . . 116.2(6) ?
O1A S1 C1 . . 108.47(11) ?
O1B S1 C8 . . 105.4(6) ?
O1A S1 C8 . . 109.77(10) ?
C1 S1 C8 . . 93.87(9) ?
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
C1 C2 . 1.387(3) ?
C1 C6 . 1.389(3) ?
C1 S1 . 1.778(2) ?
C2 C3 . 1.369(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.380(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.385(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.388(3) ?
C5 H5A . 0.9300 ?
C6 N1 . 1.428(2) ?
C7 C12 . 1.384(3) ?
C7 C8 . 1.385(3) ?
C7 N1 . 1.436(2) ?
C8 C9 . 1.394(3) ?
C8 S1 . 1.786(2) ?
C9 C10 . 1.377(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.371(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.388(3) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 O2 . 1.209(2) ?
C13 N1 . 1.387(2) ?
C13 C14 . 1.500(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
S1 O1B . 1.433(5) ?
S1 O1A . 1.4700(17) ?
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
_geom_hbond_publ_flag
C5 H5A O1A 2_545 0.93 2.31 3.207(3) 163 yes
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
C6 C1 C2 C3 . . . . -1.4(3) ?
S1 C1 C2 C3 . . . . 177.45(17) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 1.7(3) ?
C3 C4 C5 C6 . . . . -2.3(3) ?
C4 C5 C6 C1 . . . . 1.1(3) ?
C4 C5 C6 N1 . . . . 174.92(18) ?
C2 C1 C6 C5 . . . . 0.8(3) ?
S1 C1 C6 C5 . . . . -178.09(14) ?
C2 C1 C6 N1 . . . . -173.37(17) ?
S1 C1 C6 N1 . . . . 7.8(2) ?
C12 C7 C8 C9 . . . . -0.4(3) ?
N1 C7 C8 C9 . . . . 177.03(17) ?
C12 C7 C8 S1 . . . . 176.25(15) ?
N1 C7 C8 S1 . . . . -6.3(2) ?
C7 C8 C9 C10 . . . . 0.9(3) ?
S1 C8 C9 C10 . . . . -175.71(16) ?
C8 C9 C10 C11 . . . . -0.2(3) ?
C9 C10 C11 C12 . . . . -1.0(3) ?
C8 C7 C12 C11 . . . . -0.8(3) ?
N1 C7 C12 C11 . . . . -178.08(18) ?
C10 C11 C12 C7 . . . . 1.5(3) ?
O2 C13 N1 C6 . . . . -175.9(2) ?
C14 C13 N1 C6 . . . . 6.2(3) ?
O2 C13 N1 C7 . . . . 6.8(3) ?
C14 C13 N1 C7 . . . . -171.17(19) ?
C5 C6 N1 C13 . . . . 54.0(3) ?
C1 C6 N1 C13 . . . . -132.1(2) ?
C5 C6 N1 C7 . . . . -128.52(19) ?
C1 C6 N1 C7 . . . . 45.4(2) ?
C12 C7 N1 C13 . . . . -51.1(3) ?
C8 C7 N1 C13 . . . . 131.6(2) ?
C12 C7 N1 C6 . . . . 131.29(19) ?
C8 C7 N1 C6 . . . . -46.0(2) ?
C2 C1 S1 O1B . . . . -116.3(7) ?
C6 C1 S1 O1B . . . . 62.6(7) ?
C2 C1 S1 O1A . . . . 22.1(2) ?
C6 C1 S1 O1A . . . . -159.03(15) ?
C2 C1 S1 C8 . . . . 134.44(17) ?
C6 C1 S1 C8 . . . . -46.70(16) ?
C7 C8 S1 O1B . . . . -72.4(6) ?
C9 C8 S1 O1B . . . . 104.2(6) ?
C7 C8 S1 O1A . . . . 157.27(16) ?
C9 C8 S1 O1A . . . . -26.1(2) ?
C7 C8 S1 C1 . . . . 46.07(16) ?
C9 C8 S1 C1 . . . . -137.28(17) ?
