#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153838.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_7153838
loop_
_publ_author_name
'Brockmeyer, Fabian'
'Schoemaker, Robin'
'Schmidtmann, Marc'
'Martens, Jürgen'
_publ_section_title
;
 Multicomponent reaction for the first synthesis of 2,2-dialkyl- and
 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines as scaffolds for various
 3,4-dihydro-2H-1,3-thiazine derivatives.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5168
_journal_page_last               5181
_journal_paper_doi               10.1039/c4ob00866a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_structural     C21H21NO2S
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.45
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.0337(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9577(7)
_cell_length_b                   6.3713(3)
_cell_length_c                   17.8868(8)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      34.95
_cell_measurement_theta_min      2.29
_cell_volume                     1804.89(14)
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT V8.34A'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            75519
_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         34.968
_diffrn_reflns_theta_min         2.295
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6901
_reflns_number_total             7935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob00866a2.cif
_cod_data_source_block           fbp1517
_cod_depositor_comments          'Adding full bibliography for 7153838.cif.'
_cod_database_code               7153838
#BEGIN Tags that were not found in dictionaries:
_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   0.927
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.76168(2) 0.72154(3) 0.26160(2) 0.01561(6) Uani 1 1 d . .
O1 O 0.58926(4) 1.09176(8) 0.35244(3) 0.01876(11) Uani 1 1 d . .
O2 O 0.57811(4) 0.77847(9) 0.49715(3) 0.01590(11) Uani 1 1 d . .
N1 N 0.62237(4) 0.73691(9) 0.32750(3) 0.01164(10) Uani 1 1 d . .
C1 C 0.61026(4) 0.91290(10) 0.36943(4) 0.01268(12) Uani 1 1 d . .
C2 C 0.63504(4) 0.79364(10) 0.44375(4) 0.01252(12) Uani 1 1 d . .
H2 H 0.6906 0.8464 0.4685 0.015 Uiso 1 1 calc R U
C3 C 0.64965(4) 0.59906(10) 0.39208(3) 0.01102(11) Uani 1 1 d . .
H3 H 0.6080 0.4843 0.3972 0.013 Uiso 1 1 calc R U
C4 C 0.64548(4) 0.70381(11) 0.25258(4) 0.01267(12) Uani 1 1 d . .
C5 C 0.61710(5) 0.48532(12) 0.22538(4) 0.01725(13) Uani 1 1 d . .
H5A H 0.6365 0.4580 0.1764 0.026 Uiso 1 1 calc R U
H5B H 0.5553 0.4772 0.2204 0.026 Uiso 1 1 calc R U
H5C H 0.6412 0.3804 0.2619 0.026 Uiso 1 1 calc R U
C6 C 0.60924(5) 0.87219(12) 0.19737(4) 0.01808(13) Uani 1 1 d . .
H6A H 0.6282 1.0107 0.2163 0.027 Uiso 1 1 calc R U
H6B H 0.5474 0.8662 0.1920 0.027 Uiso 1 1 calc R U
H6C H 0.6288 0.8480 0.1482 0.027 Uiso 1 1 calc R U
C7 C 0.79002(4) 0.56496(11) 0.34277(4) 0.01301(12) Uani 1 1 d . .
C8 C 0.73860(4) 0.51566(11) 0.39509(3) 0.01207(11) Uani 1 1 d . .
C9 C 0.88006(4) 0.49942(11) 0.34599(4) 0.01313(12) Uani 1 1 d . .
C10 C 0.94111(5) 0.58203(13) 0.40033(4) 0.01942(14) Uani 1 1 d . .
H10 H 0.9250 0.6798 0.4361 0.023 Uiso 1 1 calc R U
C11 C 1.02537(5) 0.52310(14) 0.40293(5) 0.02176(15) Uani 1 1 d . .
H11 H 1.0664 0.5806 0.4403 0.026 Uiso 1 1 calc R U
C12 C 1.04939(5) 0.38079(14) 0.35110(5) 0.02142(15) Uani 1 1 d . .
H12 H 1.1069 0.3401 0.3530 0.026 Uiso 1 1 calc R U
C13 C 0.98914(5) 0.29728(13) 0.29613(5) 0.02150(15) Uani 1 1 d . .
H13 H 1.0055 0.1994 0.2606 0.026 Uiso 1 1 calc R U
C14 C 0.90513(5) 0.35752(12) 0.29347(4) 0.01749(13) Uani 1 1 d . .
H14 H 0.8643 0.3016 0.2555 0.021 Uiso 1 1 calc R U
C15 C 0.76409(4) 0.37005(11) 0.45915(4) 0.01279(12) Uani 1 1 d . .
C16 C 0.73899(5) 0.41193(13) 0.53015(4) 0.01850(14) Uani 1 1 d . .
H16 H 0.7067 0.5342 0.5370 0.022 Uiso 1 1 calc R U
C17 C 0.76067(6) 0.27718(14) 0.59087(4) 0.02088(15) Uani 1 1 d . .
H17 H 0.7431 0.3087 0.6385 0.025 Uiso 1 1 calc R U
C18 C 0.80750(5) 0.09810(13) 0.58229(4) 0.02001(14) Uani 1 1 d . .
H18 H 0.8229 0.0074 0.6239 0.024 Uiso 1 1 calc R U
C19 C 0.83174(5) 0.05253(12) 0.51202(4) 0.02027(14) Uani 1 1 d . .
H19 H 0.8635 -0.0708 0.5056 0.024 Uiso 1 1 calc R U
C20 C 0.80995(5) 0.18584(11) 0.45083(4) 0.01657(13) Uani 1 1 d . .
H20 H 0.8264 0.1513 0.4031 0.020 Uiso 1 1 calc R U
C21 C 0.49199(5) 0.75016(13) 0.46531(5) 0.01862(14) Uani 1 1 d . .
H21A H 0.4563 0.7355 0.5059 0.028 Uiso 1 1 calc R U
H21B H 0.4873 0.6234 0.4340 0.028 Uiso 1 1 calc R U
H21C H 0.4735 0.8722 0.4342 0.028 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'
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
C7 S1 C4 100.95(3)
C2 O2 C21 114.11(6)
C1 N1 C4 133.77(6)
C1 N1 C3 96.10(5)
C4 N1 C3 123.66(5)
O1 C1 N1 132.88(6)
O1 C1 C2 135.40(6)
N1 C1 C2 91.72(5)
O2 C2 C1 120.24(6)
O2 C2 C3 119.96(5)
C1 C2 C3 85.58(5)
O2 C2 H2 109.6
C1 C2 H2 109.6
C3 C2 H2 109.6
N1 C3 C8 115.07(5)
N1 C3 C2 86.58(5)
C8 C3 C2 117.41(5)
N1 C3 H3 111.8
C8 C3 H3 111.8
C2 C3 H3 111.8
N1 C4 C6 112.20(6)
N1 C4 C5 109.19(5)
C6 C4 C5 111.21(6)
N1 C4 S1 106.09(4)
C6 C4 S1 108.14(5)
C5 C4 S1 109.87(5)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C9 124.80(6)
C8 C7 S1 125.49(5)
C9 C7 S1 109.70(4)
C7 C8 C15 122.93(6)
C7 C8 C3 122.66(6)
C15 C8 C3 114.38(5)
C10 C9 C14 118.71(6)
C10 C9 C7 120.65(6)
C14 C9 C7 120.62(6)
C11 C10 C9 120.79(7)
C11 C10 H10 119.6
C9 C10 H10 119.6
C12 C11 C10 120.02(7)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 119.92(7)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 119.86(7)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C9 120.68(7)
C13 C14 H14 119.7
C9 C14 H14 119.7
C20 C15 C16 117.79(6)
C20 C15 C8 122.44(6)
C16 C15 C8 119.72(6)
C17 C16 C15 121.12(7)
C17 C16 H16 119.4
C15 C16 H16 119.4
C18 C17 C16 120.51(7)
C18 C17 H17 119.7
C16 C17 H17 119.7
C17 C18 C19 119.12(7)
C17 C18 H18 120.4
C19 C18 H18 120.4
C18 C19 C20 120.78(7)
C18 C19 H19 119.6
C20 C19 H19 119.6
C19 C20 C15 120.67(7)
C19 C20 H20 119.7
C15 C20 H20 119.7
O2 C21 H21A 109.5
O2 C21 H21B 109.5
H21A C21 H21B 109.5
O2 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.7738(7)
S1 C4 1.8450(7)
O1 C1 1.2158(8)
O2 C2 1.3997(8)
O2 C21 1.4331(10)
N1 C1 1.3757(9)
N1 C4 1.4483(9)
N1 C3 1.4737(8)
C1 C2 1.5402(9)
C2 C3 1.5806(9)
C2 H2 1.0000
C3 C8 1.5105(9)
C3 H3 1.0000
C4 C6 1.5233(10)
C4 C5 1.5250(10)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.3549(9)
C7 C9 1.4907(9)
C8 C15 1.4915(9)
C9 C10 1.3926(10)
C9 C14 1.3971(10)
C10 C11 1.3912(11)
C10 H10 0.9500
C11 C12 1.3841(12)
C11 H11 0.9500
C12 C13 1.3939(12)
C12 H12 0.9500
C13 C14 1.3897(11)
C13 H13 0.9500
C14 H14 0.9500
C15 C20 1.4007(10)
C15 C16 1.4032(9)
C16 C17 1.3944(10)
C16 H16 0.9500
C17 C18 1.3827(12)
C17 H17 0.9500
C18 C19 1.3904(11)
C18 H18 0.9500
C19 C20 1.3953(10)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
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 O1 26.87(13)
C3 N1 C1 O1 177.84(8)
C4 N1 C1 C2 -152.22(7)
C3 N1 C1 C2 -1.25(5)
C21 O2 C2 C1 38.31(8)
C21 O2 C2 C3 -65.17(8)
O1 C1 C2 O2 59.79(11)
N1 C1 C2 O2 -121.16(6)
O1 C1 C2 C3 -177.88(9)
N1 C1 C2 C3 1.17(5)
C1 N1 C3 C8 -117.54(6)
C4 N1 C3 C8 37.56(9)
C1 N1 C3 C2 1.22(5)
C4 N1 C3 C2 156.32(6)
O2 C2 C3 N1 121.48(6)
C1 C2 C3 N1 -1.09(5)
O2 C2 C3 C8 -121.96(7)
C1 C2 C3 C8 115.47(6)
C1 N1 C4 C6 -34.72(10)
C3 N1 C4 C6 -179.28(6)
C1 N1 C4 C5 -158.48(7)
C3 N1 C4 C5 56.96(8)
C1 N1 C4 S1 83.17(8)
C3 N1 C4 S1 -61.39(7)
C7 S1 C4 N1 45.62(5)
C7 S1 C4 C6 166.17(5)
C7 S1 C4 C5 -72.29(5)
C4 S1 C7 C8 -20.03(7)
C4 S1 C7 C9 161.37(5)
C9 C7 C8 C15 -6.32(11)
S1 C7 C8 C15 175.29(5)
C9 C7 C8 C3 175.47(6)
S1 C7 C8 C3 -2.92(10)
N1 C3 C8 C7 0.54(9)
C2 C3 C8 C7 -99.15(8)
N1 C3 C8 C15 -177.81(6)
C2 C3 C8 C15 82.50(7)
C8 C7 C9 C10 -68.89(10)
S1 C7 C9 C10 109.72(7)
C8 C7 C9 C14 112.57(8)
S1 C7 C9 C14 -68.82(8)
C14 C9 C10 C11 -0.66(12)
C7 C9 C10 C11 -179.22(7)
C9 C10 C11 C12 0.01(13)
C10 C11 C12 C13 0.26(13)
C11 C12 C13 C14 0.12(13)
C12 C13 C14 C9 -0.78(13)
C10 C9 C14 C13 1.04(12)
C7 C9 C14 C13 179.60(7)
C7 C8 C15 C20 -40.43(10)
C3 C8 C15 C20 137.92(7)
C7 C8 C15 C16 142.16(7)
C3 C8 C15 C16 -39.49(9)
C20 C15 C16 C17 1.47(11)
C8 C15 C16 C17 179.00(7)
C15 C16 C17 C18 -0.14(13)
C16 C17 C18 C19 -0.87(13)
C17 C18 C19 C20 0.52(13)
C18 C19 C20 C15 0.84(12)
C16 C15 C20 C19 -1.81(11)
C8 C15 C20 C19 -179.27(7)
