#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507317.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_4507317
loop_
_publ_author_name
'Perlovich, German L.'
'Proshin, Alexey N.'
'Ol’khovich, Marina V.'
'Sharapova, Angelica V.'
'Lermontov, Anatoly S.'
_publ_section_title
;
 Novel Spiro-Derivatives of 1,3-Thiazine Molecular Crystals: Structural
 and Thermodynamic Aspects
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              804
_journal_paper_doi               10.1021/cg301511x
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C15 H19 Br N2 S'
_chemical_formula_weight         339.29
_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                 104.832(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.000(3)
_cell_length_b                   15.170(3)
_cell_length_c                   7.7773(16)
_cell_measurement_reflns_used    3375
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.69
_cell_volume                     1482.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11921
_diffrn_reflns_theta_full        26.58
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.1902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0692
_reflns_number_gt                2511
_reflns_number_total             3090
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg301511x_si_005.cif
_cod_data_source_block           CCDC_894492
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4507317
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
_atom_site_refinement_flags
N1 N 0.47832(14) 0.25020(12) -0.0617(3) 0.0234(4) Uani 1 1 d .
C5 C 0.21991(16) 0.24683(13) 0.0607(3) 0.0240(5) Uani 1 1 d .
H5A H 0.1731 0.2856 0.0998 0.029 Uiso 1 1 calc R
C4 C 0.19504(16) 0.15875(14) 0.0332(3) 0.0227(4) Uani 1 1 d .
C3 C 0.26270(17) 0.10153(14) -0.0216(3) 0.0252(5) Uani 1 1 d .
H3A H 0.2445 0.0410 -0.0409 0.030 Uiso 1 1 calc R
C2 C 0.35730(17) 0.13286(13) -0.0484(3) 0.0234(5) Uani 1 1 d .
H2A H 0.4045 0.0935 -0.0849 0.028 Uiso 1 1 calc R
C1 C 0.38374(15) 0.22149(13) -0.0224(3) 0.0196(4) Uani 1 1 d .
C6 C 0.31389(16) 0.27821(13) 0.0306(3) 0.0222(4) Uani 1 1 d .
H6A H 0.3307 0.3391 0.0465 0.027 Uiso 1 1 calc R
S1 S 0.63243(4) 0.34452(4) -0.11528(7) 0.02568(14) Uani 1 1 d .
N2 N 0.53162(13) 0.35566(11) 0.1573(2) 0.0208(4) Uani 1 1 d .
C15 C 0.88281(18) 0.31056(15) 0.1067(3) 0.0333(5) Uani 1 1 d .
H15A H 0.8443 0.2626 0.0304 0.040 Uiso 1 1 calc R
H15B H 0.9364 0.2833 0.2063 0.040 Uiso 1 1 calc R
C12 C 0.78419(17) 0.47151(13) -0.0712(3) 0.0266(5) Uani 1 1 d .
H12A H 0.7313 0.5003 -0.1698 0.032 Uiso 1 1 calc R
H12B H 0.8254 0.5185 0.0044 0.032 Uiso 1 1 calc R
C8 C 0.54155(15) 0.31924(13) 0.0151(3) 0.0194(4) Uani 1 1 d .
C16 C 0.80420(17) 0.36374(14) 0.1810(3) 0.0270(5) Uani 1 1 d .
H16A H 0.8446 0.4045 0.2733 0.032 Uiso 1 1 calc R
H16B H 0.7641 0.3229 0.2390 0.032 Uiso 1 1 calc R
C10 C 0.65699(16) 0.47847(13) 0.1216(3) 0.0241(5) Uani 1 1 d .
H10A H 0.7037 0.5235 0.1946 0.029 Uiso 1 1 calc R
H10B H 0.6056 0.5095 0.0245 0.029 Uiso 1 1 calc R
C9 C 0.59600(16) 0.43123(14) 0.2370(3) 0.0253(5) Uani 1 1 d .
H9A H 0.6478 0.4110 0.3465 0.030 Uiso 1 1 calc R
H9B H 0.5486 0.4746 0.2731 0.030 Uiso 1 1 calc R
C14 C 0.93924(17) 0.36802(16) -0.0017(3) 0.0340(5) Uani 1 1 d .
H14A H 0.9851 0.4113 0.0777 0.041 Uiso 1 1 calc R
H14B H 0.9853 0.3306 -0.0551 0.041 Uiso 1 1 calc R
C11 C 0.72507(15) 0.41722(13) 0.0401(3) 0.0204(4) Uani 1 1 d .
C13 C 0.85949(17) 0.41662(15) -0.1486(3) 0.0309(5) Uani 1 1 d .
H13A H 0.8980 0.4555 -0.2132 0.037 Uiso 1 1 calc R
H13B H 0.8180 0.3735 -0.2344 0.037 Uiso 1 1 calc R
Br1 Br 0.067731(17) 0.113865(16) 0.07808(3) 0.03561(9) Uani 1 1 d .
H1N H 0.495(2) 0.2218(16) -0.135(4) 0.035(7) 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'
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 N1 C1 126.91(18)
C8 N1 H1N 118.8(19)
C1 N1 H1N 114.2(19)
C4 C5 C6 119.26(19)
C4 C5 H5A 120.4
C6 C5 H5A 120.4
C5 C4 C3 121.03(19)
C5 C4 Br1 119.93(15)
C3 C4 Br1 119.02(16)
C4 C3 C2 119.50(19)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C3 C2 C1 120.46(19)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C6 C1 C2 119.13(18)
C6 C1 N1 123.10(18)
C2 C1 N1 117.66(18)
C5 C6 C1 120.61(19)
C5 C6 H6A 119.7
C1 C6 H6A 119.7
C8 S1 C11 99.97(9)
C8 N2 C9 122.35(17)
C16 C15 C14 111.75(19)
C16 C15 H15A 109.3
C14 C15 H15A 109.3
C16 C15 H15B 109.3
C14 C15 H15B 109.3
H15A C15 H15B 107.9
C13 C12 C11 113.26(17)
C13 C12 H12A 108.9
C11 C12 H12A 108.9
C13 C12 H12B 108.9
C11 C12 H12B 108.9
H12A C12 H12B 107.7
N2 C8 N1 121.86(18)
N2 C8 S1 129.04(16)
N1 C8 S1 109.09(15)
C15 C16 C11 113.67(18)
C15 C16 H16A 108.8
C11 C16 H16A 108.8
C15 C16 H16B 108.8
C11 C16 H16B 108.8
H16A C16 H16B 107.7
C9 C10 C11 113.78(17)
C9 C10 H10A 108.8
C11 C10 H10A 108.8
C9 C10 H10B 108.8
C11 C10 H10B 108.8
H10A C10 H10B 107.7
N2 C9 C10 116.64(17)
N2 C9 H9A 108.1
C10 C9 H9A 108.1
N2 C9 H9B 108.1
C10 C9 H9B 108.1
H9A C9 H9B 107.3
C13 C14 C15 111.11(18)
C13 C14 H14A 109.4
C15 C14 H14A 109.4
C13 C14 H14B 109.4
C15 C14 H14B 109.4
H14A C14 H14B 108.0
C16 C11 C10 112.32(17)
C16 C11 C12 110.27(17)
C10 C11 C12 109.53(17)
C16 C11 S1 111.09(14)
C10 C11 S1 106.61(13)
C12 C11 S1 106.82(14)
C12 C13 C14 110.61(19)
C12 C13 H13A 109.5
C14 C13 H13A 109.5
C12 C13 H13B 109.5
C14 C13 H13B 109.5
H13A C13 H13B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.370(3)
N1 C1 1.410(3)
N1 H1N 0.79(3)
C5 C4 1.378(3)
C5 C6 1.386(3)
C5 H5A 0.9500
C4 C3 1.379(3)
C4 Br1 1.903(2)
C3 C2 1.383(3)
C3 H3A 0.9500
C2 C1 1.390(3)
C2 H2A 0.9500
C1 C6 1.388(3)
C6 H6A 0.9500
S1 C8 1.784(2)
S1 C11 1.839(2)
N2 C8 1.272(3)
N2 C9 1.461(3)
C15 C16 1.527(3)
C15 C14 1.525(3)
C15 H15A 0.9900
C15 H15B 0.9900
C12 C13 1.522(3)
C12 C11 1.536(3)
C12 H12A 0.9900
C12 H12B 0.9900
C16 C11 1.530(3)
C16 H16A 0.9900
C16 H16B 0.9900
C10 C9 1.520(3)
C10 C11 1.528(3)
C10 H10A 0.9900
C10 H10B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C14 C13 1.522(3)
C14 H14A 0.9900
C14 H14B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.79(3) 2.15(3) 2.934(3) 176(3) 4_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652508
2 PubChem 90671458
