#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235048.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_2235048
loop_
_publ_author_name
'Shafiq, Muhammad'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Bukhari, Iftikhar Hussain'
Ejaz
_publ_section_title
;
 1-Ethyl-4-[1-(1-phenylethylidene)hydrazin-2-ylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione
;
_journal_coeditor_code           HB6798
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1927
_journal_paper_doi               10.1107/S1600536812022982
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H19 N3 O2 S'
_chemical_formula_moiety         'C18 H19 N3 O2 S'
_chemical_formula_sum            'C18 H19 N3 O2 S'
_chemical_formula_weight         341.42
_chemical_name_systematic
1-Ethyl-4-[1-(1-phenylethylidene)hydrazin-2-ylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione
_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                 100.7250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7278(3)
_cell_length_b                   12.4327(3)
_cell_length_c                   14.2607(4)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.35
_cell_volume                     1694.60(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16049
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.316
_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     219
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0895P)²+0.2125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2887
_reflns_number_total             4129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6798.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235048
_cod_database_fobs_code          2235048
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_symmetry_multiplicity
S S1 0.78767(5) 0.93644(4) 1.05780(3) 0.04426(17) Uani d . 1 1
O O1 0.85670(16) 1.03503(13) 1.08838(12) 0.0650(4) Uani d . 1 1
O O2 0.71460(14) 0.88277(12) 1.12183(10) 0.0557(4) Uani d . 1 1
N N1 0.68626(18) 0.95785(12) 0.95522(11) 0.0477(4) Uani d . 1 1
N N2 0.89644(17) 0.66151(14) 0.96946(13) 0.0556(4) Uani d . 1 1
N N3 1.02548(17) 0.65607(14) 1.03083(13) 0.0558(5) Uani d . 1 1
C C1 0.62452(18) 0.86638(14) 0.90335(12) 0.0367(4) Uani d . 1 1
C C2 0.49509(19) 0.87561(16) 0.84347(14) 0.0458(5) Uani d . 1 1
H H2 0.4487 0.9414 0.8380 0.055 Uiso calc R 1 1
C C3 0.43489(19) 0.78866(17) 0.79221(14) 0.0496(5) Uani d . 1 1
H H3 0.3487 0.7963 0.7518 0.059 Uiso calc R 1 1
C C4 0.50112(19) 0.69015(17) 0.80018(14) 0.0477(5) Uani d . 1 1
H H4 0.4594 0.6311 0.7662 0.057 Uiso calc R 1 1
C C5 0.62979(19) 0.68026(15) 0.85904(13) 0.0428(4) Uani d . 1 1
H H5 0.6744 0.6138 0.8645 0.051 Uiso calc R 1 1
C C6 0.69472(16) 0.76729(14) 0.91056(12) 0.0355(4) Uani d . 1 1
C C7 0.83541(17) 0.75244(15) 0.96944(13) 0.0401(4) Uani d . 1 1
C C8 0.90722(18) 0.84518(16) 1.02506(14) 0.0473(5) Uani d . 1 1
H H8A 0.9653 0.8820 0.9869 0.057 Uiso calc R 1 1
H H8B 0.9677 0.8183 1.0821 0.057 Uiso calc R 1 1
C C9 1.1295(2) 0.62777(15) 0.99497(15) 0.0497(5) Uani d . 1 1
C C10 1.26558(19) 0.62074(14) 1.06248(13) 0.0428(4) Uani d . 1 1
C C11 1.3907(2) 0.6245(2) 1.03087(17) 0.0634(6) Uani d . 1 1
H H11 1.3910 0.6287 0.9658 0.076 Uiso calc R 1 1
C C12 1.5168(2) 0.6219(2) 1.09532(19) 0.0724(7) Uani d . 1 1
H H12 1.6007 0.6258 1.0731 0.087 Uiso calc R 1 1
C C13 1.5185(2) 0.61366(18) 1.19091(17) 0.0589(6) Uani d . 1 1
H H13 1.6030 0.6108 1.2338 0.071 Uiso calc R 1 1
C C14 1.3945(2) 0.60965(17) 1.22303(15) 0.0534(5) Uani d . 1 1
H H14 1.3951 0.6043 1.2882 0.064 Uiso calc R 1 1
C C15 1.2685(2) 0.61348(15) 1.15988(14) 0.0471(5) Uani d . 1 1
H H15 1.1851 0.6112 1.1828 0.057 Uiso calc R 1 1
C C16 0.6440(2) 1.06836(15) 0.92463(15) 0.0509(5) Uani d . 1 1
H H16A 0.6842 1.1183 0.9745 0.061 Uiso calc R 1 1
H H16B 0.5430 1.0742 0.9159 0.061 Uiso calc R 1 1
C C17 0.6891(3) 1.0986(2) 0.83489(19) 0.0788(8) Uani d . 1 1
H H17A 0.7893 1.0963 0.8440 0.118 Uiso calc R 1 1
H H17B 0.6572 1.1701 0.8170 0.118 Uiso calc R 1 1
H H17C 0.6500 1.0492 0.7854 0.118 Uiso calc R 1 1
C C18 1.1213(3) 0.6043(3) 0.89159(19) 0.0970(10) Uani d . 1 1
H H18A 1.0284 0.5811 0.8643 0.146 Uiso calc R 1 1
H H18B 1.1868 0.5485 0.8844 0.146 Uiso calc R 1 1
H H18C 1.1436 0.6681 0.8596 0.146 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
O2 S1 O1 118.02(10)
O2 S1 N1 111.22(9)
O1 S1 N1 107.84(9)
O2 S1 C8 107.66(9)
O1 S1 C8 109.90(9)
N1 S1 C8 100.84(9)
C1 N1 C16 121.41(15)
C1 N1 S1 117.52(12)
C16 N1 S1 120.46(13)
C7 N2 N3 114.08(16)
C9 N3 N2 117.05(18)
C2 C1 C6 119.40(16)
C2 C1 N1 119.94(16)
C6 C1 N1 120.64(15)
C3 C2 C1 120.69(17)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.59(17)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 119.17(17)
C5 C4 H4 120.4
C3 C4 H4 120.4
C4 C5 C6 121.62(17)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C6 C1 118.50(15)
C5 C6 C7 118.95(15)
C1 C6 C7 122.54(15)
N2 C7 C6 119.48(16)
N2 C7 C8 120.71(16)
C6 C7 C8 119.76(15)
C7 C8 S1 111.91(12)
C7 C8 H8A 109.2
S1 C8 H8A 109.2
C7 C8 H8B 109.2
S1 C8 H8B 109.2
H8A C8 H8B 107.9
N3 C9 C10 115.90(18)
N3 C9 C18 123.7(2)
C10 C9 C18 120.4(2)
C11 C10 C15 118.41(18)
C11 C10 C9 121.41(19)
C15 C10 C9 120.15(18)
C10 C11 C12 120.6(2)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 120.5(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.3(2)
C12 C13 H13 120.3
C14 C13 H13 120.3
C13 C14 C15 120.7(2)
C13 C14 H14 119.6
C15 C14 H14 119.6
C14 C15 C10 120.42(19)
C14 C15 H15 119.8
C10 C15 H15 119.8
N1 C16 C17 112.46(18)
N1 C16 H16A 109.1
C17 C16 H16A 109.1
N1 C16 H16B 109.1
C17 C16 H16B 109.1
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C9 C18 H18A 109.5
C9 C18 H18B 109.5
H18A C18 H18B 109.5
C9 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4232(15)
S1 O1 1.4264(15)
S1 N1 1.6270(16)
S1 C8 1.7493(19)
N1 C1 1.427(2)
N1 C16 1.477(2)
N2 C7 1.277(2)
N2 N3 1.392(2)
N3 C9 1.266(3)
C1 C2 1.388(2)
C1 C6 1.403(2)
C2 C3 1.373(3)
C2 H2 0.9300
C3 C4 1.379(3)
C3 H3 0.9300
C4 C5 1.377(2)
C4 H4 0.9300
C5 C6 1.392(3)
C5 H5 0.9300
C6 C7 1.478(2)
C7 C8 1.497(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.487(3)
C9 C18 1.490(3)
C10 C11 1.376(3)
C10 C15 1.387(3)
C11 C12 1.390(3)
C11 H11 0.9300
C12 C13 1.364(3)
C12 H12 0.9300
C13 C14 1.368(3)
C13 H13 0.9300
C14 C15 1.380(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.477(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C8 H8A O1 3_777 0.97 2.43 3.390(2) 170
C16 H16B O2 3_677 0.97 2.52 3.481(2) 171
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
O2 S1 N1 C1 -59.42(16)
O1 S1 N1 C1 169.72(14)
C8 S1 N1 C1 54.52(16)
O2 S1 N1 C16 111.72(17)
O1 S1 N1 C16 -19.14(19)
C8 S1 N1 C16 -134.34(16)
C7 N2 N3 C9 -125.1(2)
C16 N1 C1 C2 -21.2(3)
S1 N1 C1 C2 149.88(15)
C16 N1 C1 C6 157.43(18)
S1 N1 C1 C6 -31.5(2)
C6 C1 C2 C3 0.7(3)
N1 C1 C2 C3 179.27(18)
C1 C2 C3 C4 0.8(3)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C1 1.5(3)
C4 C5 C6 C7 -177.54(17)
C2 C1 C6 C5 -1.8(3)
N1 C1 C6 C5 179.60(17)
C2 C1 C6 C7 177.25(16)
N1 C1 C6 C7 -1.4(3)
N3 N2 C7 C6 -177.29(16)
N3 N2 C7 C8 5.3(3)
C5 C6 C7 N2 2.3(3)
C1 C6 C7 N2 -176.73(18)
C5 C6 C7 C8 179.76(17)
C1 C6 C7 C8 0.7(3)
N2 C7 C8 S1 -153.81(16)
C6 C7 C8 S1 28.8(2)
O2 S1 C8 C7 64.98(16)
O1 S1 C8 C7 -165.27(14)
N1 S1 C8 C7 -51.62(16)
N2 N3 C9 C10 -178.94(16)
N2 N3 C9 C18 2.2(3)
N3 C9 C10 C11 -159.4(2)
C18 C9 C10 C11 19.5(3)
N3 C9 C10 C15 18.7(3)
C18 C9 C10 C15 -162.4(2)
C15 C10 C11 C12 -0.5(3)
C9 C10 C11 C12 177.6(2)
C10 C11 C12 C13 1.2(4)
C11 C12 C13 C14 -1.0(4)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C10 0.4(3)
C11 C10 C15 C14 -0.3(3)
C9 C10 C15 C14 -178.37(18)
C1 N1 C16 C17 -69.1(3)
S1 N1 C16 C17 120.06(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657765
