#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:15:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180471 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/40/7214070.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7214070
loop_
_publ_author_name
'Clark, Ewan R.'
'Hayward, John J.'
'Leontowicz, Bryce J.'
'Eisler, Dana J.'
'Rawson, Jeremy M.'
_publ_section_title
;
 Syntheses of, and structural studies on, benzo-fused 1,2,4-thiadiazines
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1755
_journal_paper_doi               10.1039/c3ce42205d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H9 N3 S'
_chemical_formula_sum            'C12 H9 N3 S'
_chemical_formula_weight         227.28
_chemical_name_systematic
; 
 ? 
;
_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                 106.7799(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6603(3)
_cell_length_b                   7.40200(10)
_cell_length_c                   18.6797(3)
_cell_measurement_reflns_used    14935
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     2073.11(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19071
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.8605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3958
_reflns_number_total             4740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42205d.txt
_cod_data_source_block           compound_4
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7214070
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
S1_1 S 0.16258(2) 0.37435(6) 0.31084(2) 0.03175(12) Uani 1 1 d
N1_1 N -0.02049(8) 0.47612(19) 0.21938(7) 0.0274(3) Uani 1 1 d
H1N_1 H -0.0720(13) 0.520(3) 0.1942(11) 0.037(5) Uiso 1 1 d
N2_1 N 0.07662(8) 0.44185(18) 0.34286(7) 0.0276(3) Uani 1 1 d
N3_1 N -0.21130(9) 0.5442(2) 0.39728(8) 0.0328(3) Uani 1 1 d
C1_1 C 0.04613(10) 0.5042(2) 0.18267(8) 0.0249(3) Uani 1 1 d
C2_1 C 0.13519(10) 0.4645(2) 0.21958(8) 0.0264(3) Uani 1 1 d
C3_1 C 0.20081(11) 0.4912(2) 0.18422(10) 0.0323(3) Uani 1 1 d
H3_1 H 0.2628(13) 0.463(3) 0.2102(10) 0.033(5) Uiso 1 1 d
C4_1 C 0.17781(12) 0.5523(2) 0.11081(10) 0.0360(4) Uani 1 1 d
H4_1 H 0.2252(12) 0.566(3) 0.0827(11) 0.036(5) Uiso 1 1 d
C5_1 C 0.08951(12) 0.5920(2) 0.07428(9) 0.0345(4) Uani 1 1 d
H5_1 H 0.0742(12) 0.638(3) 0.0244(11) 0.037(5) Uiso 1 1 d
C6_1 C 0.02354(11) 0.5704(2) 0.11034(9) 0.0299(3) Uani 1 1 d
H6_1 H -0.0338(13) 0.602(2) 0.0867(10) 0.029(4) Uiso 1 1 d
C7_1 C -0.00018(9) 0.4760(2) 0.29626(8) 0.0246(3) Uani 1 1 d
C8_1 C -0.07475(9) 0.5081(2) 0.32908(8) 0.0246(3) Uani 1 1 d
C9_1 C -0.05768(10) 0.5738(2) 0.40169(9) 0.0286(3) Uani 1 1 d
H9_1 H 0.0031(14) 0.607(3) 0.4289(11) 0.040(5) Uiso 1 1 d
C10_1 C -0.12717(11) 0.5905(2) 0.43293(9) 0.0317(3) Uani 1 1 d
H10_1 H -0.1181(13) 0.637(3) 0.4808(12) 0.039(5) Uiso 1 1 d
C12_1 C -0.22693(11) 0.4819(3) 0.32755(9) 0.0354(4) Uani 1 1 d
H12_1 H -0.2874(14) 0.448(3) 0.3035(11) 0.043(5) Uiso 1 1 d
C13_1 C -0.16230(10) 0.4635(2) 0.29099(9) 0.0311(3) Uani 1 1 d
H13_1 H -0.1794(13) 0.415(3) 0.2421(11) 0.038(5) Uiso 1 1 d
S1_2 S 0.58698(3) -0.09279(6) 0.11744(3) 0.03689(13) Uani 1 1 d
N1_2 N 0.39383(9) -0.0230(2) 0.09286(8) 0.0337(3) Uani 1 1 d
H1N_2 H 0.3376(15) -0.005(3) 0.0851(12) 0.046(6) Uiso 1 1 d
N2_2 N 0.50033(8) -0.19926(19) 0.05543(7) 0.0313(3) Uani 1 1 d
N3_2 N 0.20767(9) -0.4692(2) -0.09205(8) 0.0345(3) Uani 1 1 d
C1_2 C 0.44868(10) 0.1241(2) 0.12501(8) 0.0287(3) Uani 1 1 d
C2_2 C 0.54081(10) 0.1122(2) 0.13745(9) 0.0300(3) Uani 1 1 d
C3_2 C 0.59420(11) 0.2605(3) 0.16554(9) 0.0369(4) Uani 1 1 d
H3_2 H 0.6566(13) 0.249(3) 0.1718(11) 0.041(5) Uiso 1 1 d
C4_2 C 0.55657(13) 0.4170(3) 0.18450(10) 0.0406(4) Uani 1 1 d
H4_2 H 0.5924(15) 0.521(3) 0.2017(13) 0.057(6) Uiso 1 1 d
C5_2 C 0.46597(13) 0.4262(3) 0.17476(10) 0.0408(4) Uani 1 1 d
H5_2 H 0.4391(13) 0.532(3) 0.1849(11) 0.042(5) Uiso 1 1 d
C6_2 C 0.41164(11) 0.2804(2) 0.14402(9) 0.0354(4) Uani 1 1 d
H6_2 H 0.3490(13) 0.288(3) 0.1340(11) 0.039(5) Uiso 1 1 d
C7_2 C 0.41993(10) -0.1562(2) 0.05243(8) 0.0265(3) Uani 1 1 d
C8_2 C 0.34656(9) -0.2635(2) 0.00154(8) 0.0259(3) Uani 1 1 d
C9_2 C 0.35905(11) -0.4439(2) -0.01286(9) 0.0309(3) Uani 1 1 d
H9_2 H 0.4138(14) -0.501(3) 0.0077(11) 0.043(5) Uiso 1 1 d
C10_2 C 0.28850(11) -0.5404(2) -0.05885(10) 0.0347(4) Uani 1 1 d
H10_2 H 0.2944(12) -0.667(3) -0.0682(10) 0.035(5) Uiso 1 1 d
C12_2 C 0.19739(10) -0.2948(2) -0.07881(9) 0.0315(3) Uani 1 1 d
H12_2 H 0.1397(13) -0.240(3) -0.1054(11) 0.039(5) Uiso 1 1 d
C13_2 C 0.26317(10) -0.1878(2) -0.03295(8) 0.0286(3) Uani 1 1 d
H13_2 H 0.2525(12) -0.070(3) -0.0268(10) 0.035(5) Uiso 1 1 d
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2_1 S1_1 C2_1 103.46(7)
C7_1 N1_1 C1_1 121.52(12)
C7_1 N1_1 H1N_1 117.5(13)
C1_1 N1_1 H1N_1 112.3(13)
C7_1 N2_1 S1_1 119.95(11)
C12_1 N3_1 C10_1 116.78(14)
C6_1 C1_1 C2_1 119.59(14)
C6_1 C1_1 N1_1 120.48(13)
C2_1 C1_1 N1_1 119.93(13)
C3_1 C2_1 C1_1 120.42(14)
C3_1 C2_1 S1_1 120.48(12)
C1_1 C2_1 S1_1 119.08(11)
C2_1 C3_1 C4_1 120.00(15)
C2_1 C3_1 H3_1 120.0(11)
C4_1 C3_1 H3_1 119.9(11)
C5_1 C4_1 C3_1 119.52(15)
C5_1 C4_1 H4_1 119.5(10)
C3_1 C4_1 H4_1 121.0(10)
C4_1 C5_1 C6_1 120.71(15)
C4_1 C5_1 H5_1 119.3(11)
C6_1 C5_1 H5_1 119.9(11)
C1_1 C6_1 C5_1 119.70(15)
C1_1 C6_1 H6_1 120.3(12)
C5_1 C6_1 H6_1 120.0(12)
N2_1 C7_1 N1_1 126.38(14)
N2_1 C7_1 C8_1 116.32(13)
N1_1 C7_1 C8_1 117.20(12)
C13_1 C8_1 C9_1 117.72(14)
C13_1 C8_1 C7_1 121.83(14)
C9_1 C8_1 C7_1 120.33(13)
C10_1 C9_1 C8_1 119.34(14)
C10_1 C9_1 H9_1 121.8(12)
C8_1 C9_1 H9_1 118.8(12)
N3_1 C10_1 C9_1 123.34(15)
N3_1 C10_1 H10_1 115.4(12)
C9_1 C10_1 H10_1 121.3(12)
N3_1 C12_1 C13_1 124.18(15)
N3_1 C12_1 H12_1 115.2(12)
C13_1 C12_1 H12_1 120.6(12)
C12_1 C13_1 C8_1 118.61(15)
C12_1 C13_1 H13_1 118.1(12)
C8_1 C13_1 H13_1 123.2(12)
N2_2 S1_2 C2_2 104.31(7)
C7_2 N1_2 C1_2 123.16(13)
C7_2 N1_2 H1N_2 118.0(15)
C1_2 N1_2 H1N_2 114.9(15)
C7_2 N2_2 S1_2 119.58(12)
C12_2 N3_2 C10_2 116.22(14)
C6_2 C1_2 C2_2 119.92(15)
C6_2 C1_2 N1_2 120.36(14)
C2_2 C1_2 N1_2 119.72(15)
C3_2 C2_2 C1_2 119.60(16)
C3_2 C2_2 S1_2 121.37(13)
C1_2 C2_2 S1_2 119.03(12)
C2_2 C3_2 C4_2 120.12(16)
C2_2 C3_2 H3_2 117.4(13)
C4_2 C3_2 H3_2 122.4(13)
C5_2 C4_2 C3_2 120.16(17)
C5_2 C4_2 H4_2 119.3(14)
C3_2 C4_2 H4_2 120.4(14)
C4_2 C5_2 C6_2 119.97(18)
C4_2 C5_2 H5_2 121.4(13)
C6_2 C5_2 H5_2 118.5(13)
C1_2 C6_2 C5_2 120.13(16)
C1_2 C6_2 H6_2 119.2(12)
C5_2 C6_2 H6_2 120.6(12)
N2_2 C7_2 N1_2 126.71(14)
N2_2 C7_2 C8_2 117.43(14)
N1_2 C7_2 C8_2 115.84(13)
C9_2 C8_2 C13_2 117.54(14)
C9_2 C8_2 C7_2 120.70(13)
C13_2 C8_2 C7_2 121.76(14)
C10_2 C9_2 C8_2 118.98(15)
C10_2 C9_2 H9_2 119.5(13)
C8_2 C9_2 H9_2 121.5(13)
N3_2 C10_2 C9_2 123.99(16)
N3_2 C10_2 H10_2 115.1(11)
C9_2 C10_2 H10_2 120.9(11)
N3_2 C12_2 C13_2 124.14(15)
N3_2 C12_2 H12_2 116.6(12)
C13_2 C12_2 H12_2 119.2(12)
C12_2 C13_2 C8_2 119.11(15)
C12_2 C13_2 H13_2 120.1(12)
C8_2 C13_2 H13_2 120.8(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1_1 N2_1 1.6984(13)
S1_1 C2_1 1.7642(15)
N1_1 C7_1 1.3782(19)
N1_1 C1_1 1.4195(19)
N1_1 H1N_1 0.87(2)
N2_1 C7_1 1.2898(19)
N3_1 C12_1 1.336(2)
N3_1 C10_1 1.338(2)
C1_1 C6_1 1.384(2)
C1_1 C2_1 1.397(2)
C2_1 C3_1 1.387(2)
C3_1 C4_1 1.389(2)
C3_1 H3_1 0.975(19)
C4_1 C5_1 1.385(3)
C4_1 H4_1 1.031(19)
C5_1 C6_1 1.396(2)
C5_1 H5_1 0.96(2)
C6_1 H6_1 0.910(19)
C7_1 C8_1 1.486(2)
C8_1 C13_1 1.390(2)
C8_1 C9_1 1.392(2)
C9_1 C10_1 1.381(2)
C9_1 H9_1 0.97(2)
C10_1 H10_1 0.93(2)
C12_1 C13_1 1.381(2)
C12_1 H12_1 0.96(2)
C13_1 H13_1 0.94(2)
S1_2 N2_2 1.7019(13)
S1_2 C2_2 1.7665(17)
N1_2 C7_2 1.374(2)
N1_2 C1_2 1.409(2)
N1_2 H1N_2 0.86(2)
N2_2 C7_2 1.2844(19)
N3_2 C12_2 1.333(2)
N3_2 C10_2 1.346(2)
C1_2 C6_2 1.386(2)
C1_2 C2_2 1.396(2)
C2_2 C3_2 1.388(2)
C3_2 C4_2 1.392(3)
C3_2 H3_2 0.95(2)
C4_2 C5_2 1.379(3)
C4_2 H4_2 0.95(2)
C5_2 C6_2 1.392(3)
C5_2 H5_2 0.93(2)
C6_2 H6_2 0.946(19)
C7_2 C8_2 1.491(2)
C8_2 C9_2 1.387(2)
C8_2 C13_2 1.396(2)
C9_2 C10_2 1.386(2)
C9_2 H9_2 0.93(2)
C10_2 H10_2 0.96(2)
C12_2 C13_2 1.383(2)
C12_2 H12_2 0.984(19)
C13_2 H13_2 0.90(2)
