#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236549.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_2236549
loop_
_publ_author_name
'Shafiq, Muhammad'
'Harrison, William T. A.'
'Khan, Islam Ullah'
_publ_section_title
;
 6-Bromo-1-methyl-4-[2-(4-nitrobenzylidene)hydrazin-1-ylidene]-2,2-dioxo-3,4-dihydro-1H-2λ⁶,1-benzothiazine
;
_journal_coeditor_code           PV2578
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2717
_journal_paper_doi               10.1107/S1600536812035374
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C16 H13 Br N4 O4 S'
_chemical_formula_sum            'C16 H13 Br N4 O4 S'
_chemical_formula_weight         437.27
_chemical_name_systematic
6-Bromo-1-methyl-4-[2-(4-nitrobenzylidene)hydrazin-1-ylidene]-2,2-dioxo-3,4-dihydro-1H-2λ⁶,1-benzothiazine
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.132(4)
_cell_angle_beta                 70.976(3)
_cell_angle_gamma                75.098(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2772(4)
_cell_length_b                   9.0572(4)
_cell_length_c                   12.6868(6)
_cell_measurement_reflns_used    4062
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.08
_cell_measurement_theta_min      2.33
_cell_volume                     868.32(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17474
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.518
_exptl_absorpt_correction_T_max  0.8434
_exptl_absorpt_correction_T_min  0.4642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0435
_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)+(0.0415P)²+0.5116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2484
_reflns_number_total             4251
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2578.cif
_cod_data_source_block           I
_cod_database_code               2236549
_cod_database_fobs_code          2236549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.8000(4) 0.2966(4) 0.3910(3) 0.0429(8) Uani d . 1 1
C C2 0.8376(5) 0.4239(4) 0.4267(3) 0.0591(10) Uani d . 1 1
H H2 0.8240 0.4365 0.5017 0.071 Uiso calc R 1 1
C C3 0.8940(5) 0.5298(4) 0.3531(3) 0.0516(9) Uani d . 1 1
H H3 0.9165 0.6146 0.3784 0.062 Uiso calc R 1 1
C C4 0.9175(4) 0.5116(3) 0.2422(3) 0.0443(8) Uani d . 1 1
C C5 0.8801(4) 0.3880(3) 0.2041(3) 0.0385(7) Uani d . 1 1
H H5 0.8956 0.3769 0.1287 0.046 Uiso calc R 1 1
C C6 0.8192(4) 0.2795(3) 0.2783(2) 0.0371(7) Uani d . 1 1
C C7 0.7760(4) 0.1511(3) 0.2351(2) 0.0336(7) Uani d . 1 1
C C8 0.7034(4) 0.0381(4) 0.3145(2) 0.0438(8) Uani d . 1 1
H H8A 0.7315 -0.0590 0.2750 0.053 Uiso calc R 1 1
H H8B 0.5757 0.0744 0.3446 0.053 Uiso calc R 1 1
C C9 0.6400(6) 0.2323(5) 0.5848(3) 0.0799(13) Uani d . 1 1
H H9A 0.7166 0.2499 0.6229 0.120 Uiso calc R 1 1
H H9B 0.5874 0.1518 0.6195 0.120 Uiso calc R 1 1
H H9C 0.5488 0.3242 0.5886 0.120 Uiso calc R 1 1
C C10 0.7637(4) 0.0248(3) -0.0055(3) 0.0390(7) Uani d . 1 1
H H10 0.8022 0.1039 -0.0472 0.047 Uiso calc R 1 1
C C11 0.7208(4) -0.0903(3) -0.0607(2) 0.0362(7) Uani d . 1 1
C C12 0.6593(4) -0.2102(4) -0.0032(2) 0.0413(7) Uani d . 1 1
H H12 0.6451 -0.2187 0.0724 0.050 Uiso calc R 1 1
C C13 0.6194(4) -0.3163(4) -0.0580(3) 0.0454(8) Uani d . 1 1
H H13 0.5775 -0.3964 -0.0199 0.054 Uiso calc R 1 1
C C14 0.6428(4) -0.3016(4) -0.1703(3) 0.0404(7) Uani d . 1 1
C C15 0.7034(4) -0.1855(4) -0.2294(3) 0.0431(8) Uani d . 1 1
H H15 0.7184 -0.1782 -0.3052 0.052 Uiso calc R 1 1
C C16 0.7415(4) -0.0794(4) -0.1731(2) 0.0414(8) Uani d . 1 1
H H16 0.7820 0.0010 -0.2116 0.050 Uiso calc R 1 1
S S1 0.79259(11) 0.01247(9) 0.42342(6) 0.0432(2) Uani d . 1 1
O O1 0.9788(3) -0.0430(3) 0.37576(19) 0.0558(6) Uani d . 1 1
O O2 0.7010(3) -0.0721(3) 0.50933(18) 0.0569(6) Uani d . 1 1
O O3 0.6135(4) -0.3959(3) -0.3268(2) 0.0759(8) Uani d . 1 1
O O4 0.5483(5) -0.5195(3) -0.1767(3) 0.0898(10) Uani d . 1 1
N N1 0.7408(4) 0.1889(3) 0.4696(2) 0.0498(7) Uani d . 1 1
N N2 0.7990(3) 0.1447(3) 0.1299(2) 0.0404(6) Uani d . 1 1
N N3 0.7509(3) 0.0216(3) 0.0964(2) 0.0396(6) Uani d . 1 1
N N4 0.5998(4) -0.4145(4) -0.2289(3) 0.0559(8) Uani d . 1 1
Br Br1 1.00058(6) 0.65482(4) 0.13996(3) 0.06700(17) Uani d . 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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 119.1(3)
C6 C1 N1 121.3(3)
C2 C1 N1 119.7(3)
C3 C2 C1 121.0(3)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 120.2(3)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 120.3(3)
C3 C4 Br1 120.3(2)
C5 C4 Br1 119.3(2)
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C1 C6 C5 118.9(3)
C1 C6 C7 122.2(3)
C5 C6 C7 118.9(3)
N2 C7 C6 117.6(3)
N2 C7 C8 123.0(2)
C6 C7 C8 119.4(2)
C7 C8 S1 110.5(2)
C7 C8 H8A 109.6
S1 C8 H8A 109.6
C7 C8 H8B 109.6
S1 C8 H8B 109.6
H8A C8 H8B 108.1
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N3 C10 C11 122.9(3)
N3 C10 H10 118.6
C11 C10 H10 118.6
C16 C11 C12 119.2(3)
C16 C11 C10 119.0(3)
C12 C11 C10 121.8(3)
C13 C12 C11 120.2(3)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 118.7(3)
C12 C13 H13 120.6
C14 C13 H13 120.6
C15 C14 C13 122.6(3)
C15 C14 N4 118.6(3)
C13 C14 N4 118.8(3)
C14 C15 C16 117.9(3)
C14 C15 H15 121.0
C16 C15 H15 121.0
C11 C16 C15 121.3(3)
C11 C16 H16 119.3
C15 C16 H16 119.3
O1 S1 O2 118.22(15)
O1 S1 N1 110.53(15)
O2 S1 N1 108.09(14)
O1 S1 C8 107.65(15)
O2 S1 C8 110.70(14)
N1 S1 C8 100.17(15)
C1 N1 C9 122.1(3)
C1 N1 S1 116.7(2)
C9 N1 S1 121.3(2)
C7 N2 N3 113.8(2)
C10 N3 N2 112.1(2)
O3 N4 O4 123.4(3)
O3 N4 C14 117.9(3)
O4 N4 C14 118.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.398(4)
C1 C2 1.400(4)
C1 N1 1.420(4)
C2 C3 1.367(5)
C2 H2 0.9300
C3 C4 1.368(4)
C3 H3 0.9300
C4 C5 1.382(4)
C4 Br1 1.884(3)
C5 C6 1.400(4)
C5 H5 0.9300
C6 C7 1.478(4)
C7 N2 1.288(4)
C7 C8 1.497(4)
C8 S1 1.748(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 N1 1.443(4)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 N3 1.262(4)
C10 C11 1.459(4)
C10 H10 0.9300
C11 C16 1.380(4)
C11 C12 1.391(4)
C12 C13 1.376(4)
C12 H12 0.9300
C13 C14 1.379(4)
C13 H13 0.9300
C14 C15 1.366(4)
C14 N4 1.470(4)
C15 C16 1.381(4)
C15 H15 0.9300
C16 H16 0.9300
S1 O1 1.420(2)
S1 O2 1.423(2)
S1 N1 1.631(3)
O3 N4 1.217(4)
O4 N4 1.219(4)
N2 N3 1.402(3)
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 H2 O3 1_566 0.93 2.56 3.325(4) 139
C8 H8B O2 2_656 0.97 2.44 3.310(4) 150
C13 H13 O4 2_645 0.93 2.53 3.306(5) 141
C15 H15 O2 1_554 0.93 2.53 3.426(4) 162
C16 H16 O1 2_755 0.93 2.45 3.218(4) 139
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
C6 C1 C2 C3 -0.6(5)
N1 C1 C2 C3 -179.7(3)
C1 C2 C3 C4 -1.1(6)
C2 C3 C4 C5 1.7(5)
C2 C3 C4 Br1 -178.5(3)
C3 C4 C5 C6 -0.5(5)
Br1 C4 C5 C6 179.6(2)
C2 C1 C6 C5 1.7(5)
N1 C1 C6 C5 -179.2(3)
C2 C1 C6 C7 -177.8(3)
N1 C1 C6 C7 1.2(5)
C4 C5 C6 C1 -1.2(5)
C4 C5 C6 C7 178.4(3)
C1 C6 C7 N2 -179.6(3)
C5 C6 C7 N2 0.8(4)
C1 C6 C7 C8 2.2(4)
C5 C6 C7 C8 -177.4(3)
N2 C7 C8 S1 148.6(3)
C6 C7 C8 S1 -33.3(4)
N3 C10 C11 C16 -178.9(3)
N3 C10 C11 C12 1.2(5)
C16 C11 C12 C13 -0.1(5)
C10 C11 C12 C13 179.7(3)
C11 C12 C13 C14 0.4(5)
C12 C13 C14 C15 -0.3(5)
C12 C13 C14 N4 -179.8(3)
C13 C14 C15 C16 -0.2(5)
N4 C14 C15 C16 179.3(3)
C12 C11 C16 C15 -0.3(5)
C10 C11 C16 C15 179.8(3)
C14 C15 C16 C11 0.5(5)
C7 C8 S1 O1 -60.1(3)
C7 C8 S1 O2 169.3(2)
C7 C8 S1 N1 55.4(2)
C6 C1 N1 C9 -149.0(4)
C2 C1 N1 C9 30.0(5)
C6 C1 N1 S1 31.0(4)
C2 C1 N1 S1 -149.9(3)
O1 S1 N1 C1 57.5(3)
O2 S1 N1 C1 -171.7(2)
C8 S1 N1 C1 -55.9(3)
O1 S1 N1 C9 -122.5(3)
O2 S1 N1 C9 8.3(4)
C8 S1 N1 C9 124.2(3)
C6 C7 N2 N3 -178.5(3)
C8 C7 N2 N3 -0.4(4)
C11 C10 N3 N2 -179.8(3)
C7 N2 N3 C10 175.5(3)
C15 C14 N4 O3 -2.8(5)
C13 C14 N4 O3 176.7(3)
C15 C14 N4 O4 178.9(3)
C13 C14 N4 O4 -1.6(5)
