#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:27:07 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252903 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157440.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_7157440
loop_
_publ_author_name
'Jiang, Jingjing'
'Tuo, Xiaolong'
'Fu, Zhuquan'
'Huang, Huawen'
'Deng, Guo-Jun'
_publ_section_title
;
 Three-component synthesis of 1,4-benzothiazines via iodide-catalyzed
 aerobic C-H sulfuration with elemental sulfur.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3234
_journal_page_last               3238
_journal_paper_doi               10.1039/d0ob00074d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C22 H18 N2 S'
_chemical_formula_sum            'C22 H18 N2 S'
_chemical_formula_weight         342.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.43(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.768(2)
_cell_length_b                   5.0226(10)
_cell_length_c                   17.193(3)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.5051
_cell_volume                     839.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1186
	          2theta: -20.0407
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1186
	          2theta: -20.0407
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0787
_diffrn_orient_matrix_UB_12      -0.0618
_diffrn_orient_matrix_UB_13      0.0239
_diffrn_orient_matrix_UB_21      0.0112
_diffrn_orient_matrix_UB_22      -0.0839
_diffrn_orient_matrix_UB_23      -0.1802
_diffrn_orient_matrix_UB_31      0.0331
_diffrn_orient_matrix_UB_32      -0.0428
_diffrn_orient_matrix_UB_33      0.0220
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6116
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       rod
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0301P)²+0.7126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                3175
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00074d2.cif
_cod_data_source_block           sa4493
_cod_depositor_comments          'Adding full bibliography for 7157440.cif.'
_cod_database_code               7157440
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_number_total             2143
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21314(13) 0.6567(3) 0.22140(7) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.4432(4) 0.8013(9) 0.3543(2) 0.0274(9) Uani 1 1 d . . . . .
N2 N 0.4087(4) 0.8909(9) 0.1469(2) 0.0304(10) Uani 1 1 d . . . . .
C1 C 0.0753(5) -0.0278(11) 0.4280(3) 0.0321(12) Uani 1 1 d . . . . .
H1A H 0.1282 -0.1826 0.4443 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.0125 -0.0713 0.3835 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.0246 0.0314 0.4700 0.048 Uiso 1 1 calc GR . . . .
C2 C 0.1700(5) 0.1891(10) 0.4067(3) 0.0266(10) Uani 1 1 d . . . . .
C3 C 0.2809(5) 0.2695(10) 0.4591(3) 0.0294(11) Uani 1 1 d . . . . .
H3 H 0.2959 0.1858 0.5074 0.035 Uiso 1 1 calc R . . . .
C4 C 0.3684(5) 0.4707(11) 0.4403(3) 0.0293(11) Uani 1 1 d . . . . .
H4 H 0.4396 0.5232 0.4768 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3520(5) 0.5974(9) 0.3673(3) 0.0257(11) Uani 1 1 d . . . . .
C6 C 0.2425(5) 0.5160(10) 0.3144(3) 0.0266(11) Uani 1 1 d . . . . .
C7 C 0.1532(5) 0.3148(11) 0.3342(3) 0.0299(11) Uani 1 1 d . . . . .
H7 H 0.0810 0.2636 0.2982 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3679(5) 0.8348(10) 0.2137(3) 0.0254(10) Uani 1 1 d . . . . .
C9 C 0.4526(5) 0.9136(10) 0.2872(3) 0.0243(10) Uani 1 1 d . . . . .
C10 C 0.5601(5) 1.1257(11) 0.2847(2) 0.0248(10) Uani 1 1 d . . . . .
C11 C 0.6634(5) 1.1404(12) 0.3469(2) 0.0305(11) Uani 1 1 d . . . . .
H11 H 0.6634 1.0186 0.3876 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7653(5) 1.3320(11) 0.3491(3) 0.0340(12) Uani 1 1 d . . . . .
H12 H 0.8319 1.3396 0.3914 0.041 Uiso 1 1 calc R . . . .
C13 C 0.7685(6) 1.5134(11) 0.2881(3) 0.0325(12) Uani 1 1 d . . . . .
H13 H 0.8380 1.6401 0.2886 0.039 Uiso 1 1 calc R . . . .
C14 C 0.6663(5) 1.5013(11) 0.2270(3) 0.0322(12) Uani 1 1 d . . . . .
H14 H 0.6666 1.6232 0.1863 0.039 Uiso 1 1 calc R . . . .
C15 C 0.5631(5) 1.3107(10) 0.2250(3) 0.0309(11) Uani 1 1 d . . . . .
H15 H 0.4953 1.3071 0.1833 0.037 Uiso 1 1 calc R . . . .
C16 C 0.3295(5) 0.8121(10) 0.0769(3) 0.0261(10) Uani 1 1 d . . . . .
C17 C 0.3812(5) 0.6133(11) 0.0319(3) 0.0341(12) Uani 1 1 d . . . . .
H17 H 0.4636 0.5291 0.0486 0.041 Uiso 1 1 calc R . . . .
C18 C 0.3087(6) 0.5416(12) -0.0381(3) 0.0370(13) Uani 1 1 d . . . . .
H18 H 0.3440 0.4085 -0.0680 0.044 Uiso 1 1 calc R . . . .
C19 C 0.1859(5) 0.6603(13) -0.0649(2) 0.0323(11) Uani 1 1 d . . . . .
C20 C 0.1373(5) 0.8623(12) -0.0205(3) 0.0362(13) Uani 1 1 d . . . . .
H20 H 0.0560 0.9487 -0.0380 0.043 Uiso 1 1 calc R . . . .
C21 C 0.2083(5) 0.9390(11) 0.0501(3) 0.0341(12) Uani 1 1 d . . . . .
H21 H 0.1742 1.0757 0.0793 0.041 Uiso 1 1 calc R . . . .
C22 C 0.1075(6) 0.5730(12) -0.1411(3) 0.0395(14) Uani 1 1 d . . . . .
H22A H 0.1705 0.5511 -0.1802 0.059 Uiso 1 1 calc GR . . . .
H22B H 0.0404 0.7058 -0.1579 0.059 Uiso 1 1 calc GR . . . .
H22C H 0.0620 0.4070 -0.1334 0.059 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C8 101.9(2) . . ?
C9 N1 C5 124.4(4) . . ?
C8 N2 C16 120.4(4) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.7(4) . . ?
C7 C2 C1 121.8(4) . . ?
C7 C2 C3 117.6(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(5) . . ?
C5 C4 H4 119.3 . . ?
N1 C5 C4 117.3(4) . . ?
N1 C5 C6 125.0(4) . . ?
C6 C5 C4 117.7(4) . . ?
C5 C6 S1 121.8(4) . . ?
C5 C6 C7 120.6(4) . . ?
C7 C6 S1 117.6(4) . . ?
C2 C7 C6 121.5(5) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 S1 121.2(4) . . ?
N2 C8 C9 120.3(4) . . ?
C9 C8 S1 118.5(3) . . ?
N1 C9 C8 123.8(4) . . ?
N1 C9 C10 116.4(4) . . ?
C8 C9 C10 119.7(4) . . ?
C11 C10 C9 118.1(4) . . ?
C15 C10 C9 124.1(4) . . ?
C15 C10 C11 117.7(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(5) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(5) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.7(4) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 N2 118.3(4) . . ?
C21 C16 N2 122.1(5) . . ?
C21 C16 C17 119.4(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.4(5) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 117.8(4) . . ?
C18 C19 C22 121.0(5) . . ?
C20 C19 C22 121.1(5) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C20 120.1(5) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.747(5) . ?
S1 C8 1.772(5) . ?
N1 C5 1.389(6) . ?
N1 C9 1.294(6) . ?
N2 C8 1.281(6) . ?
N2 C16 1.424(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.497(7) . ?
C2 C3 1.401(6) . ?
C2 C7 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.403(6) . ?
C5 C6 1.398(6) . ?
C6 C7 1.398(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.498(6) . ?
C9 C10 1.500(7) . ?
C10 C11 1.400(6) . ?
C10 C15 1.387(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(7) . ?
C16 C21 1.384(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(7) . ?
C19 C20 1.380(8) . ?
C19 C22 1.519(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.395(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C6 C7 C2 179.2(4) . . . . ?
S1 C8 C9 N1 20.1(7) . . . . ?
S1 C8 C9 C10 -162.8(4) . . . . ?
N1 C5 C6 S1 3.2(7) . . . . ?
N1 C5 C6 C7 -177.6(5) . . . . ?
N1 C9 C10 C11 16.1(7) . . . . ?
N1 C9 C10 C15 -163.2(5) . . . . ?
N2 C8 C9 N1 -158.4(5) . . . . ?
N2 C8 C9 C10 18.7(7) . . . . ?
N2 C16 C17 C18 -177.3(5) . . . . ?
N2 C16 C21 C20 177.3(5) . . . . ?
C1 C2 C3 C4 -179.5(5) . . . . ?
C1 C2 C7 C6 -179.6(5) . . . . ?
C2 C3 C4 C5 -1.8(8) . . . . ?
C3 C2 C7 C6 -0.7(8) . . . . ?
C3 C4 C5 N1 178.7(5) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 S1 -179.2(4) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C5 N1 C9 C8 -1.3(8) . . . . ?
C5 N1 C9 C10 -178.5(4) . . . . ?
C5 C6 C7 C2 0.0(8) . . . . ?
C6 S1 C8 N2 155.9(4) . . . . ?
C6 S1 C8 C9 -22.6(4) . . . . ?
C7 C2 C3 C4 1.6(8) . . . . ?
C8 S1 C6 C5 12.4(5) . . . . ?
C8 S1 C6 C7 -166.7(4) . . . . ?
C8 N2 C16 C17 -110.1(6) . . . . ?
C8 N2 C16 C21 74.2(7) . . . . ?
C8 C9 C10 C11 -161.3(5) . . . . ?
C8 C9 C10 C15 19.4(7) . . . . ?
C9 N1 C5 C4 170.8(5) . . . . ?
C9 N1 C5 C6 -11.7(8) . . . . ?
C9 C10 C11 C12 -179.4(4) . . . . ?
C9 C10 C15 C14 180.0(5) . . . . ?
C10 C11 C12 C13 -1.1(8) . . . . ?
C11 C10 C15 C14 0.7(7) . . . . ?
C11 C12 C13 C14 1.6(8) . . . . ?
C12 C13 C14 C15 -0.9(8) . . . . ?
C13 C14 C15 C10 -0.2(8) . . . . ?
C15 C10 C11 C12 -0.1(8) . . . . ?
C16 N2 C8 S1 0.4(7) . . . . ?
C16 N2 C8 C9 178.9(4) . . . . ?
C16 C17 C18 C19 -0.2(8) . . . . ?
C17 C16 C21 C20 1.6(8) . . . . ?
C17 C18 C19 C20 1.7(9) . . . . ?
C17 C18 C19 C22 -178.7(5) . . . . ?
C18 C19 C20 C21 -1.6(8) . . . . ?
C19 C20 C21 C16 -0.1(8) . . . . ?
C21 C16 C17 C18 -1.5(8) . . . . ?
C22 C19 C20 C21 178.9(5) . . . . ?
