#------------------------------------------------------------------------------
#$Date: 2015-07-11 01:48:43 +0300 (Sat, 11 Jul 2015) $
#$Revision: 143737 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154503.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_7154503
loop_
_publ_author_name
'Kröger, Denis'
'Brockmeyer, Fabian'
'Kahrs, Christoph'
_publ_section_title
;
 A three-component reaction for rapid access to underexplored
 1,3-thiazine-2-thiones.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7223
_journal_page_last               7229
_journal_paper_doi               10.1039/c5ob00377f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_structural     C21H19NS2
_chemical_formula_sum            'C21 H19 N S2'
_chemical_formula_weight         349.49
_chemical_name_systematic        6b
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-02-13 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.4793(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1457(4)
_cell_length_b                   21.3132(9)
_cell_length_c                   9.5797(4)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      34.91
_cell_measurement_theta_min      2.48
_cell_volume                     1737.63(13)
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT V8.34A'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            66281
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.969
_diffrn_reflns_theta_min         1.911
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         7639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6769
_reflns_number_total             7639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob00377f2.cif
_cod_data_source_block           lhdk290
_cod_depositor_comments
'Adding full bibliography for 7154503--7154504.cif.'
_cod_database_code               7154503
_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.
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.964
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_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
S1 S 0.86915(2) 0.58860(2) -0.03033(2) 0.01615(5) Uani 1 1 d . .
S2 S 0.66825(3) 0.54899(2) -0.32119(3) 0.02045(5) Uani 1 1 d . .
N1 N 0.55515(8) 0.60171(4) -0.12666(8) 0.01588(12) Uani 1 1 d . .
C1 C 0.55624(9) 0.62871(4) 0.01595(9) 0.01380(13) Uani 1 1 d . .
H1 H 0.4911 0.6677 -0.0107 0.017 Uiso 1 1 calc R U
C2 C 0.71408(9) 0.64757(4) 0.12884(9) 0.01362(13) Uani 1 1 d . .
C3 C 0.85311(9) 0.63153(4) 0.12146(9) 0.01356(13) Uani 1 1 d . .
C4 C 0.67700(9) 0.58164(4) -0.15953(9) 0.01400(13) Uani 1 1 d . .
C5 C 0.39502(10) 0.59593(5) -0.23887(10) 0.02110(17) Uani 1 1 d . .
H5A H 0.3976 0.5691 -0.3223 0.025 Uiso 1 1 calc R U
H5B H 0.3572 0.6380 -0.2805 0.025 Uiso 1 1 calc R U
C6 C 0.28152(10) 0.56836(4) -0.17513(11) 0.01917(15) Uani 1 1 d . .
C7 C 0.31773(10) 0.56216(4) -0.02817(11) 0.01957(15) Uani 1 1 d . .
H7 H 0.2428 0.5435 0.0063 0.023 Uiso 1 1 calc R U
C8 C 0.47164(10) 0.58335(4) 0.08566(10) 0.01798(15) Uani 1 1 d . .
H8A H 0.5393 0.5464 0.1266 0.022 Uiso 1 1 calc R U
H8B H 0.4529 0.6045 0.1697 0.022 Uiso 1 1 calc R U
C9 C 0.12692(12) 0.54902(6) -0.29185(14) 0.0305(2) Uani 1 1 d . .
H9A H 0.1437 0.5140 -0.3506 0.046 Uiso 1 1 calc R U
H9B H 0.0812 0.5845 -0.3585 0.046 Uiso 1 1 calc R U
H9C H 0.0551 0.5359 -0.2425 0.046 Uiso 1 1 calc R U
C10 C 0.70511(9) 0.68620(4) 0.25525(9) 0.01465(13) Uani 1 1 d . .
C11 C 0.76448(10) 0.66392(5) 0.40285(10) 0.01922(15) Uani 1 1 d . .
H11 H 0.8060 0.6226 0.4231 0.023 Uiso 1 1 calc R U
C12 C 0.76284(11) 0.70220(5) 0.52042(10) 0.02285(18) Uani 1 1 d . .
H12 H 0.8030 0.6868 0.6205 0.027 Uiso 1 1 calc R U
C13 C 0.70265(11) 0.76268(5) 0.49167(11) 0.02289(18) Uani 1 1 d . .
H13 H 0.7060 0.7893 0.5723 0.027 Uiso 1 1 calc R U
C14 C 0.63759(11) 0.78412(5) 0.34485(11) 0.02095(16) Uani 1 1 d . .
H14 H 0.5925 0.8249 0.3248 0.025 Uiso 1 1 calc R U
C15 C 0.63825(10) 0.74608(4) 0.22683(10) 0.01715(14) Uani 1 1 d . .
H15 H 0.5931 0.7609 0.1266 0.021 Uiso 1 1 calc R U
C16 C 1.01132(9) 0.65067(4) 0.22752(9) 0.01374(13) Uani 1 1 d . .
C17 C 1.13226(10) 0.60618(4) 0.27625(10) 0.01681(14) Uani 1 1 d . .
H17 H 1.1107 0.5635 0.2471 0.020 Uiso 1 1 calc R U
C18 C 1.28402(10) 0.62400(5) 0.36726(10) 0.01973(16) Uani 1 1 d . .
H18 H 1.3651 0.5934 0.4008 0.024 Uiso 1 1 calc R U
C19 C 1.31673(11) 0.68634(5) 0.40891(10) 0.02165(17) Uani 1 1 d . .
H19 H 1.4203 0.6985 0.4703 0.026 Uiso 1 1 calc R U
C20 C 1.19748(11) 0.73096(5) 0.36065(10) 0.02067(16) Uani 1 1 d . .
H20 H 1.2200 0.7736 0.3892 0.025 Uiso 1 1 calc R U
C21 C 1.04540(10) 0.71341(4) 0.27077(10) 0.01684(14) Uani 1 1 d . .
H21 H 0.9645 0.7441 0.2387 0.020 Uiso 1 1 calc R U
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
C4 S1 C3 105.17(4)
C4 N1 C5 119.66(7)
C4 N1 C1 128.23(7)
C5 N1 C1 112.07(7)
N1 C1 C2 116.57(6)
N1 C1 C8 108.82(7)
C2 C1 C8 111.02(7)
N1 C1 H1 106.6
C2 C1 H1 106.6
C8 C1 H1 106.6
C3 C2 C10 121.18(7)
C3 C2 C1 124.80(7)
C10 C2 C1 114.01(7)
C2 C3 C16 126.63(7)
C2 C3 S1 122.67(6)
C16 C3 S1 110.51(6)
N1 C4 S2 126.21(6)
N1 C4 S1 121.07(6)
S2 C4 S1 112.71(5)
N1 C5 C6 112.75(8)
N1 C5 H5A 109.0
C6 C5 H5A 109.0
N1 C5 H5B 109.0
C6 C5 H5B 109.0
H5A C5 H5B 107.8
C7 C6 C5 121.85(8)
C7 C6 C9 124.19(9)
C5 C6 C9 113.97(9)
C6 C7 C8 122.92(8)
C6 C7 H7 118.5
C8 C7 H7 118.5
C7 C8 C1 111.19(7)
C7 C8 H8A 109.4
C1 C8 H8A 109.4
C7 C8 H8B 109.4
C1 C8 H8B 109.4
H8A C8 H8B 108.0
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C15 C10 C11 119.12(8)
C15 C10 C2 119.73(7)
C11 C10 C2 121.14(8)
C12 C11 C10 120.18(9)
C12 C11 H11 119.9
C10 C11 H11 119.9
C13 C12 C11 120.21(9)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 119.87(9)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.19(9)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C10 120.32(8)
C14 C15 H15 119.8
C10 C15 H15 119.8
C21 C16 C17 118.98(8)
C21 C16 C3 121.25(7)
C17 C16 C3 119.58(7)
C18 C17 C16 120.51(8)
C18 C17 H17 119.7
C16 C17 H17 119.7
C19 C18 C17 120.05(8)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C20 119.88(8)
C18 C19 H19 120.1
C20 C19 H19 120.1
C19 C20 C21 120.36(9)
C19 C20 H20 119.8
C21 C20 H20 119.8
C20 C21 C16 120.20(8)
C20 C21 H21 119.9
C16 C21 H21 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.7462(8)
S1 C3 1.7690(8)
S2 C4 1.6728(8)
N1 C4 1.3345(11)
N1 C5 1.4706(11)
N1 C1 1.4791(11)
C1 C2 1.5072(11)
C1 C8 1.5356(12)
C1 H1 1.0000
C2 C3 1.3433(11)
C2 C10 1.4912(11)
C3 C16 1.4885(11)
C5 C6 1.5033(13)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.3296(14)
C6 C9 1.5038(13)
C7 C8 1.5001(13)
C7 H7 0.9500
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C15 1.3983(12)
C10 C11 1.3990(12)
C11 C12 1.3951(13)
C11 H11 0.9500
C12 C13 1.3891(16)
C12 H12 0.9500
C13 C14 1.3886(15)
C13 H13 0.9500
C14 C15 1.3931(12)
C14 H14 0.9500
C15 H15 0.9500
C16 C21 1.4008(12)
C16 C17 1.4007(12)
C17 C18 1.3944(12)
C17 H17 0.9500
C18 C19 1.3879(14)
C18 H18 0.9500
C19 C20 1.3923(15)
C19 H19 0.9500
C20 C21 1.3924(13)
C20 H20 0.9500
C21 H21 0.9500
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
C4 N1 C1 C2 12.78(13)
C5 N1 C1 C2 -169.34(7)
C4 N1 C1 C8 -113.67(9)
C5 N1 C1 C8 64.22(9)
N1 C1 C2 C3 -12.68(12)
C8 C1 C2 C3 112.66(9)
N1 C1 C2 C10 168.00(7)
C8 C1 C2 C10 -66.66(9)
C10 C2 C3 C16 -2.76(13)
C1 C2 C3 C16 177.97(8)
C10 C2 C3 S1 -177.28(6)
C1 C2 C3 S1 3.44(12)
C4 S1 C3 C2 5.46(8)
C4 S1 C3 C16 -169.86(6)
C5 N1 C4 S2 -0.13(12)
C1 N1 C4 S2 177.61(7)
C5 N1 C4 S1 179.14(7)
C1 N1 C4 S1 -3.12(13)
C3 S1 C4 N1 -5.70(8)
C3 S1 C4 S2 173.66(4)
C4 N1 C5 C6 132.33(9)
C1 N1 C5 C6 -45.75(11)
N1 C5 C6 C7 12.41(13)
N1 C5 C6 C9 -167.55(8)
C5 C6 C7 C8 1.56(15)
C9 C6 C7 C8 -178.48(9)
C6 C7 C8 C1 16.67(13)
N1 C1 C8 C7 -47.84(9)
C2 C1 C8 C7 -177.41(7)
C3 C2 C10 C15 115.53(9)
C1 C2 C10 C15 -65.12(10)
C3 C2 C10 C11 -63.61(11)
C1 C2 C10 C11 115.74(9)
C15 C10 C11 C12 -2.75(13)
C2 C10 C11 C12 176.40(8)
C10 C11 C12 C13 -0.17(14)
C11 C12 C13 C14 2.86(14)
C12 C13 C14 C15 -2.60(14)
C13 C14 C15 C10 -0.35(13)
C11 C10 C15 C14 3.01(13)
C2 C10 C15 C14 -176.15(8)
C2 C3 C16 C21 -48.37(13)
S1 C3 C16 C21 126.71(7)
C2 C3 C16 C17 136.64(9)
S1 C3 C16 C17 -48.28(9)
C21 C16 C17 C18 0.44(13)
C3 C16 C17 C18 175.54(8)
C16 C17 C18 C19 -0.74(13)
C17 C18 C19 C20 0.51(14)
C18 C19 C20 C21 0.02(14)
C19 C20 C21 C16 -0.32(13)
C17 C16 C21 C20 0.09(13)
C3 C16 C21 C20 -174.92(8)
