#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507323.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_4507323
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 H20 N2 S'
_chemical_formula_weight         260.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.517(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.235(3)
_cell_length_b                   19.286(8)
_cell_length_c                   11.982(5)
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.78
_cell_measurement_theta_min      2.72
_cell_volume                     1431.5(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11001
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0609
_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)+(0.0909P)²+0.7452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                1918
_reflns_number_total             2800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg301511x_si_011.cif
_cod_data_source_block           CCDC_894498
_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_cell_volume        1431.4(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4507323
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
S1 S 0.84590(13) 0.08039(4) 0.78017(6) 0.0541(3) Uani 1 1 d .
N1 N 0.5591(4) -0.00696(13) 0.85201(19) 0.0518(6) Uani 1 1 d .
N2 N 0.7279(5) 0.06184(16) 0.9886(2) 0.0615(7) Uani 1 1 d D
C13 C 0.9983(8) 0.2574(3) 0.6772(4) 0.1048(16) Uani 1 1 d .
H13A H 0.9533 0.2706 0.6000 0.126 Uiso 1 1 calc R
H13B H 1.0765 0.2963 0.7137 0.126 Uiso 1 1 calc R
C14 C 0.8044(8) 0.2442(2) 0.7340(4) 0.0902(13) Uani 1 1 d .
H14A H 0.7126 0.2116 0.6894 0.108 Uiso 1 1 calc R
H14B H 0.7246 0.2872 0.7372 0.108 Uiso 1 1 calc R
C15 C 0.8520(6) 0.21612(19) 0.8503(3) 0.0758(11) Uani 1 1 d .
H15A H 0.9239 0.2516 0.8982 0.091 Uiso 1 1 calc R
H15B H 0.7171 0.2050 0.8793 0.091 Uiso 1 1 calc R
C10 C 0.9898(5) 0.15328(16) 0.8557(3) 0.0533(8) Uani 1 1 d .
C7 C 0.6982(5) 0.04152(15) 0.8810(2) 0.0461(7) Uani 1 1 d .
C1 C 0.5251(5) -0.03355(14) 0.7415(2) 0.0451(7) Uani 1 1 d .
C2 C 0.3188(5) -0.03183(17) 0.6848(3) 0.0596(8) Uani 1 1 d .
H2A H 0.2071 -0.0114 0.7183 0.071 Uiso 1 1 calc R
C3 C 0.2781(6) -0.0603(2) 0.5787(3) 0.0737(10) Uani 1 1 d .
H3A H 0.1395 -0.0580 0.5409 0.088 Uiso 1 1 calc R
C4 C 0.4385(7) -0.09175(19) 0.5284(3) 0.0702(10) Uani 1 1 d .
H4A H 0.4098 -0.1109 0.4570 0.084 Uiso 1 1 calc R
C11 C 1.1953(6) 0.1653(2) 0.7971(4) 0.0883(13) Uani 1 1 d .
H11A H 1.2683 0.1213 0.7904 0.106 Uiso 1 1 calc R
H11B H 1.2925 0.1957 0.8434 0.106 Uiso 1 1 calc R
C12 C 1.1442(8) 0.1982(3) 0.6777(4) 0.0979(14) Uani 1 1 d .
H12A H 1.2781 0.2130 0.6510 0.117 Uiso 1 1 calc R
H12B H 1.0796 0.1633 0.6262 0.117 Uiso 1 1 calc R
C8 C 0.8755(6) 0.1125(2) 1.0399(3) 0.0726(11) Uani 1 1 d .
H8A H 0.9321 0.0960 1.1139 0.087 Uiso 1 1 calc R
H8B H 0.7967 0.1550 1.0497 0.087 Uiso 1 1 calc R
C9 C 1.0589(6) 0.1284(2) 0.9759(3) 0.0819(12) Uani 1 1 d .
H9A H 1.1471 0.0871 0.9730 0.098 Uiso 1 1 calc R
H9B H 1.1474 0.1639 1.0156 0.098 Uiso 1 1 calc R
C5 C 0.6394(6) -0.09457(17) 0.5839(3) 0.0637(9) Uani 1 1 d .
H5A H 0.7493 -0.1158 0.5502 0.076 Uiso 1 1 calc R
C6 C 0.6845(5) -0.06633(16) 0.6904(3) 0.0535(8) Uani 1 1 d .
H6A H 0.8233 -0.0695 0.7277 0.064 Uiso 1 1 calc R
H2N H 0.649(5) 0.0435(17) 1.033(2) 0.064 Uiso 1 1 d 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 S1 C10 104.46(14)
C7 N1 C1 122.6(2)
C7 N2 C8 128.6(3)
C7 N2 H2N 117(2)
C8 N2 H2N 114(2)
C12 C13 C14 113.9(4)
C12 C13 H13A 108.8
C14 C13 H13A 108.8
C12 C13 H13B 108.8
C14 C13 H13B 108.8
H13A C13 H13B 107.7
C13 C14 C15 114.0(4)
C13 C14 H14A 108.8
C15 C14 H14A 108.8
C13 C14 H14B 108.8
C15 C14 H14B 108.8
H14A C14 H14B 107.6
C10 C15 C14 112.9(3)
C10 C15 H15A 109.0
C14 C15 H15A 109.0
C10 C15 H15B 109.0
C14 C15 H15B 109.0
H15A C15 H15B 107.8
C15 C10 C9 113.3(3)
C15 C10 C11 111.3(3)
C9 C10 C11 108.3(3)
C15 C10 S1 110.7(2)
C9 C10 S1 106.9(2)
C11 C10 S1 105.9(2)
N1 C7 N2 119.0(3)
N1 C7 S1 120.5(2)
N2 C7 S1 120.5(2)
C6 C1 C2 118.0(3)
C6 C1 N1 122.9(3)
C2 C1 N1 118.9(3)
C3 C2 C1 120.4(3)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C4 C3 C2 121.0(3)
C4 C3 H3A 119.5
C2 C3 H3A 119.5
C5 C4 C3 119.0(3)
C5 C4 H4A 120.5
C3 C4 H4A 120.5
C10 C11 C12 112.5(3)
C10 C11 H11A 109.1
C12 C11 H11A 109.1
C10 C11 H11B 109.1
C12 C11 H11B 109.1
H11A C11 H11B 107.8
C13 C12 C11 112.5(4)
C13 C12 H12A 109.1
C11 C12 H12A 109.1
C13 C12 H12B 109.1
C11 C12 H12B 109.1
H12A C12 H12B 107.8
N2 C8 C9 114.6(3)
N2 C8 H8A 108.6
C9 C8 H8A 108.6
N2 C8 H8B 108.6
C9 C8 H8B 108.6
H8A C8 H8B 107.6
C8 C9 C10 113.6(3)
C8 C9 H9A 108.8
C10 C9 H9A 108.8
C8 C9 H9B 108.8
C10 C9 H9B 108.8
H9A C9 H9B 107.7
C4 C5 C6 121.2(3)
C4 C5 H5A 119.4
C6 C5 H5A 119.4
C1 C6 C5 120.5(3)
C1 C6 H6A 119.7
C5 C6 H6A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.767(3)
S1 C10 1.848(3)
N1 C7 1.295(4)
N1 C1 1.413(3)
N2 C7 1.340(4)
N2 C8 1.431(4)
N2 H2N 0.843(18)
C13 C12 1.460(7)
C13 C14 1.476(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.494(6)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C10 1.482(5)
C15 H15A 0.9700
C15 H15B 0.9700
C10 C9 1.534(5)
C10 C11 1.547(5)
C1 C6 1.378(4)
C1 C2 1.386(4)
C2 C3 1.381(5)
C2 H2A 0.9300
C3 C4 1.367(5)
C3 H3A 0.9300
C4 C5 1.351(5)
C4 H4A 0.9300
C11 C12 1.565(6)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12A 0.9700
C12 H12B 0.9700
C8 C9 1.479(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C5 C6 1.386(4)
C5 H5A 0.9300
C6 H6A 0.9300
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
N2 H2N N1 0.843(18) 2.117(19) 2.957(4) 175(3) 3_657
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652513
2 PubChem 90671463
