#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/20/7222041.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_7222041
loop_
_publ_author_name
'preet, Simer'
'Cannoo, Damanjit Singh'
_publ_section_title
;
 Base induced synthesis of 4H-1,4-benzothiazines and their computational
 studies
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA12442E
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C16 H12 Br N O S'
_chemical_formula_weight         346.24
_chemical_name_systematic
(4-Bromothenyl)(4-Methyl-4H-Benzo(b)(1,4)Thiazin-2-yl)Methanone
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_update_record
;
2015-02-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.150(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7172(19)
_cell_length_b                   9.2242(17)
_cell_length_c                   13.153(2)
_cell_measurement_reflns_used    1278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9831
_cell_measurement_theta_min      3.2512
_cell_volume                     1419.5(4)
_computing_cell_refinement       'CrysAlis Pro, Agilent Technologies'
_computing_data_collection       'CrysAlis Pro, Agilent Technologies'
_computing_data_reduction        'CrysAlis Pro, Agilent Technologies'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0919
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5637
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.05
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis Pro, Agilent Technologies'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0587
_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)+(0.0544P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                1872
_reflns_number_total             3220
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra12442e2.cif
_cod_data_source_block           b1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1419.4(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7222041
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_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
_atom_site_refinement_flags
Br Br 0.35903(4) -0.03638(6) 0.63035(4) 0.0540(2) Uani 1 1 d .
S1 S 1.09799(10) 0.13085(13) 0.66744(10) 0.0431(3) Uani 1 1 d .
O1 O 0.9302(3) -0.0444(3) 0.7530(3) 0.0503(9) Uani 1 1 d .
N1 N 0.9770(3) 0.2582(4) 0.4685(3) 0.0369(9) Uani 1 1 d .
C5 C 0.6854(4) 0.1338(5) 0.6467(3) 0.0377(12) Uani 1 1 d .
H005 H 0.7172 0.2261 0.6446 0.045 Uiso 1 1 calc R
C2 C 0.5898(4) -0.1404(5) 0.6499(4) 0.0417(12) Uani 1 1 d .
H006 H 0.5577 -0.2326 0.6497 0.050 Uiso 1 1 calc R
C15 C 1.3021(5) 0.4321(5) 0.5545(5) 0.0532(14) Uani 1 1 d .
H007 H 1.3735 0.4705 0.5737 0.064 Uiso 1 1 calc R
C7 C 0.8834(4) 0.0266(5) 0.6820(4) 0.0338(11) Uani 1 1 d .
C8 C 0.9532(4) 0.1194(5) 0.6223(3) 0.0329(11) Uani 1 1 d .
C10 C 1.0872(4) 0.3157(5) 0.4979(3) 0.0336(11) Uani 1 1 d .
C4 C 0.7575(4) 0.0144(5) 0.6603(3) 0.0323(11) Uani 1 1 d .
C9 C 0.9161(4) 0.1762(4) 0.5323(3) 0.0337(11) Uani 1 1 d .
H012 H 0.8405 0.1573 0.5114 0.040 Uiso 1 1 calc R
C11 C 1.1458(4) 0.2707(4) 0.5877(3) 0.0347(11) Uani 1 1 d .
C16 C 1.2506(4) 0.3333(5) 0.6159(4) 0.0450(13) Uani 1 1 d .
H014 H 1.2870 0.3079 0.6779 0.054 Uiso 1 1 calc R
C6 C 0.5690(4) 0.1190(5) 0.6362(3) 0.0374(11) Uani 1 1 d .
H015 H 0.5227 0.2005 0.6276 0.045 Uiso 1 1 calc R
C12 C 0.9213(4) 0.3039(5) 0.3714(3) 0.0470(13) Uani 1 1 d .
H01A H 0.9734 0.3616 0.3347 0.071 Uiso 1 1 calc R
H01B H 0.8546 0.3602 0.3840 0.071 Uiso 1 1 calc R
H01C H 0.8994 0.2200 0.3319 0.071 Uiso 1 1 calc R
C3 C 0.7065(4) -0.1220(5) 0.6616(4) 0.0411(12) Uani 1 1 d .
H017 H 0.7528 -0.2034 0.6705 0.049 Uiso 1 1 calc R
C14 C 1.2461(5) 0.4729(5) 0.4644(4) 0.0508(14) Uani 1 1 d .
H018 H 1.2804 0.5377 0.4214 0.061 Uiso 1 1 calc R
C13 C 1.1395(4) 0.4182(5) 0.4377(4) 0.0447(13) Uani 1 1 d .
H019 H 1.1013 0.4502 0.3780 0.054 Uiso 1 1 calc R
C1 C 0.5208(4) -0.0174(5) 0.6386(3) 0.0355(11) Uani 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C8 S1 C11 99.9(2)
C9 N1 C10 122.4(4)
C9 N1 C12 118.3(4)
C10 N1 C12 118.8(4)
C6 C5 C4 121.8(4)
C6 C5 H005 119.1
C4 C5 H005 119.1
C3 C2 C1 118.5(4)
C3 C2 H006 120.8
C1 C2 H006 120.8
C14 C15 C16 118.8(5)
C14 C15 H007 120.6
C16 C15 H007 120.6
O1 C7 C8 118.8(4)
O1 C7 C4 119.7(4)
C8 C7 C4 121.6(4)
C9 C8 C7 123.0(4)
C9 C8 S1 122.0(3)
C7 C8 S1 114.4(3)
C11 C10 C13 118.1(5)
C11 C10 N1 120.9(4)
C13 C10 N1 121.1(4)
C3 C4 C5 117.3(4)
C3 C4 C7 119.1(4)
C5 C4 C7 123.4(4)
C8 C9 N1 127.2(4)
C8 C9 H012 116.4
N1 C9 H012 116.4
C16 C11 C10 119.2(4)
C16 C11 S1 116.6(4)
C10 C11 S1 124.1(4)
C15 C16 C11 121.9(5)
C15 C16 H014 119.1
C11 C16 H014 119.1
C5 C6 C1 119.7(4)
C5 C6 H015 120.2
C1 C6 H015 120.2
N1 C12 H01A 109.5
N1 C12 H01B 109.5
H01A C12 H01B 109.5
N1 C12 H01C 109.5
H01A C12 H01C 109.5
H01B C12 H01C 109.5
C2 C3 C4 122.2(4)
C2 C3 H017 118.9
C4 C3 H017 118.9
C13 C14 C15 120.3(5)
C13 C14 H018 119.9
C15 C14 H018 119.9
C14 C13 C10 121.6(5)
C14 C13 H019 119.2
C10 C13 H019 119.2
C6 C1 C2 120.5(4)
C6 C1 Br 119.4(3)
C2 C1 Br 120.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.900(5)
S1 C8 1.770(5)
S1 C11 1.773(4)
O1 C7 1.242(5)
N1 C9 1.360(5)
N1 C10 1.430(5)
N1 C12 1.464(5)
C5 C6 1.370(6)
C5 C4 1.394(6)
C5 H005 0.9300
C2 C3 1.379(6)
C2 C1 1.397(6)
C2 H006 0.9300
C15 C14 1.375(8)
C15 C16 1.379(6)
C15 H007 0.9300
C7 C8 1.446(6)
C7 C4 1.491(6)
C8 C9 1.344(6)
C10 C11 1.396(6)
C10 C13 1.397(6)
C4 C3 1.393(6)
C9 H012 0.9300
C11 C16 1.389(6)
C16 H014 0.9300
C6 C1 1.380(6)
C6 H015 0.9300
C12 H01A 0.9600
C12 H01B 0.9600
C12 H01C 0.9600
C3 H017 0.9300
C14 C13 1.374(7)
C14 H018 0.9300
C13 H019 0.9300
