#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507316.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_4507316
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            'C16 H20 N2 O S'
_chemical_formula_weight         288.40
_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                 110.1320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6555(6)
_cell_length_b                   13.1733(9)
_cell_length_c                   12.7112(8)
_cell_measurement_reflns_used    5983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.30
_cell_volume                     1518.02(17)
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14226
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.9037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0365
_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)+(0.0573P)²+0.2050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2824
_reflns_number_total             3317
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg301511x_si_004.cif
_cod_data_source_block           CCDC_894491
_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)/n
_cod_database_code               4507316
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
S1 S 0.05066(4) 0.23117(3) 0.71527(3) 0.04792(13) Uani 1 1 d
N1 N -0.04628(12) 0.05557(8) 0.73069(9) 0.0420(3) Uani 1 1 d
C2 C -0.14244(13) -0.11286(9) 0.69015(10) 0.0391(3) Uani 1 1 d
N2 N 0.08699(13) 0.12887(9) 0.90645(9) 0.0441(3) Uani 1 1 d
O1 O -0.04411(13) -0.05113(8) 0.87628(8) 0.0585(3) Uani 1 1 d
C8 C 0.02997(13) 0.12945(9) 0.79612(10) 0.0390(3) Uani 1 1 d
C11 C 0.15876(13) 0.32666(10) 0.81590(10) 0.0430(3) Uani 1 1 d
C1 C -0.07259(14) -0.03281(10) 0.77538(10) 0.0405(3) Uani 1 1 d
C12 C 0.25009(17) 0.38215(13) 0.75617(15) 0.0570(4) Uani 1 1 d
C7 C -0.16564(16) -0.20928(11) 0.72451(13) 0.0470(3) Uani 1 1 d
C9 C 0.17649(19) 0.20824(12) 0.97764(12) 0.0559(4) Uani 1 1 d
C16 C 0.05709(17) 0.40130(11) 0.84578(12) 0.0488(3) Uani 1 1 d
C10 C 0.25925(17) 0.27019(13) 0.91862(14) 0.0557(4) Uani 1 1 d
C15 C -0.03358(19) 0.46805(13) 0.74872(15) 0.0582(4) Uani 1 1 d
C5 C -0.2750(2) -0.26359(13) 0.53515(15) 0.0628(4) Uani 1 1 d
C6 C -0.23180(18) -0.28377(11) 0.64726(15) 0.0537(4) Uani 1 1 d
C3 C -0.1843(2) -0.09396(12) 0.57653(13) 0.0588(4) Uani 1 1 d
C13 C 0.1549(2) 0.44407(14) 0.65649(15) 0.0623(4) Uani 1 1 d
C14 C 0.0616(2) 0.51992(14) 0.69052(16) 0.0664(5) Uani 1 1 d
C4 C -0.2504(3) -0.16920(14) 0.49993(15) 0.0752(5) Uani 1 1 d
H16B H -0.0096(18) 0.3664(12) 0.8765(13) 0.053(4) Uiso 1 1 d
H10B H 0.328(2) 0.2293(14) 0.8973(16) 0.068(5) Uiso 1 1 d
H2B H 0.0603(19) 0.0780(15) 0.9369(15) 0.062(5) Uiso 1 1 d
H9B H 0.247(2) 0.1730(14) 1.0404(15) 0.072(5) Uiso 1 1 d
H9A H 0.106(2) 0.2521(15) 1.0083(17) 0.075(6) Uiso 1 1 d
H13B H 0.0920(19) 0.3981(13) 0.5986(14) 0.058(4) Uiso 1 1 d
H12B H 0.3145(19) 0.4290(13) 0.8120(14) 0.059(4) Uiso 1 1 d
H10A H 0.313(2) 0.3197(14) 0.9687(14) 0.062(5) Uiso 1 1 d
H7A H -0.135(2) -0.2212(14) 0.8027(17) 0.065(5) Uiso 1 1 d
H12A H 0.313(2) 0.3309(14) 0.7354(14) 0.064(5) Uiso 1 1 d
H13A H 0.219(2) 0.4749(15) 0.6230(16) 0.076(6) Uiso 1 1 d
H16A H 0.1180(19) 0.4463(13) 0.9048(15) 0.061(5) Uiso 1 1 d
H15B H -0.109(2) 0.4236(14) 0.6955(15) 0.062(5) Uiso 1 1 d
H14B H 0.000(2) 0.5583(16) 0.6254(19) 0.087(6) Uiso 1 1 d
H15A H -0.090(2) 0.5192(16) 0.7759(16) 0.077(6) Uiso 1 1 d
H5A H -0.320(2) -0.3159(15) 0.4819(16) 0.075(5) Uiso 1 1 d
H6A H -0.246(2) -0.3481(15) 0.6724(16) 0.077(6) Uiso 1 1 d
H14A H 0.132(2) 0.5695(16) 0.7432(18) 0.085(6) Uiso 1 1 d
H3A H -0.162(2) -0.0326(15) 0.5544(16) 0.071(5) Uiso 1 1 d
H4A H -0.270(3) -0.1556(17) 0.423(2) 0.095(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'
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
C8 S1 C11 105.58(6)
C8 N1 C1 120.69(11)
C3 C2 C7 118.27(13)
C3 C2 C1 121.79(12)
C7 C2 C1 119.95(12)
C8 N2 C9 126.73(12)
C8 N2 H2B 113.8(12)
C9 N2 H2B 119.2(12)
N2 C8 N1 126.95(12)
N2 C8 S1 122.78(10)
N1 C8 S1 110.25(9)
C10 C11 C16 112.03(12)
C10 C11 C12 110.59(12)
C16 C11 C12 110.17(12)
C10 C11 S1 107.63(10)
C16 C11 S1 110.70(9)
C12 C11 S1 105.48(10)
O1 C1 N1 126.40(12)
O1 C1 C2 119.75(12)
N1 C1 C2 113.85(11)
C13 C12 C11 112.49(13)
C13 C12 H12B 108.4(10)
C11 C12 H12B 105.7(10)
C13 C12 H12A 112.9(10)
C11 C12 H12A 108.3(10)
H12B C12 H12A 108.7(14)
C6 C7 C2 120.86(14)
C6 C7 H7A 122.0(11)
C2 C7 H7A 117.1(11)
N2 C9 C10 112.43(13)
N2 C9 H9B 105.4(11)
C10 C9 H9B 109.0(11)
N2 C9 H9A 107.5(11)
C10 C9 H9A 113.7(11)
H9B C9 H9A 108.4(15)
C15 C16 C11 114.21(13)
C15 C16 H16B 108.8(9)
C11 C16 H16B 111.5(9)
C15 C16 H16A 107.3(10)
C11 C16 H16A 108.2(10)
H16B C16 H16A 106.5(14)
C9 C10 C11 113.53(13)
C9 C10 H10B 111.9(11)
C11 C10 H10B 109.2(11)
C9 C10 H10A 107.5(10)
C11 C10 H10A 106.4(11)
H10B C10 H10A 108.1(16)
C16 C15 C14 112.17(14)
C16 C15 H15B 107.0(10)
C14 C15 H15B 110.7(10)
C16 C15 H15A 109.8(11)
C14 C15 H15A 110.8(11)
H15B C15 H15A 106.1(15)
C6 C5 C4 119.51(15)
C6 C5 H5A 119.8(11)
C4 C5 H5A 120.7(11)
C5 C6 C7 120.29(15)
C5 C6 H6A 120.5(12)
C7 C6 H6A 119.2(12)
C2 C3 C4 120.35(15)
C2 C3 H3A 118.1(12)
C4 C3 H3A 121.5(12)
C14 C13 C12 111.50(15)
C14 C13 H13B 110.3(10)
C12 C13 H13B 109.5(10)
C14 C13 H13A 113.0(11)
C12 C13 H13A 107.5(12)
H13B C13 H13A 104.8(15)
C13 C14 C15 111.23(14)
C13 C14 H14B 110.6(13)
C15 C14 H14B 110.4(13)
C13 C14 H14A 106.8(12)
C15 C14 H14A 110.2(12)
H14B C14 H14A 107.5(17)
C5 C4 C3 120.71(16)
C5 C4 H4A 121.0(14)
C3 C4 H4A 118.0(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.7416(13)
S1 C11 1.8409(13)
N1 C8 1.3264(17)
N1 C1 1.3572(16)
C2 C3 1.382(2)
C2 C7 1.3862(19)
C2 C1 1.4960(18)
N2 C8 1.3184(17)
N2 C9 1.4563(19)
N2 H2B 0.857(19)
O1 C1 1.2394(15)
C11 C10 1.5256(19)
C11 C16 1.527(2)
C11 C12 1.5328(19)
C12 C13 1.521(2)
C12 H12B 0.983(18)
C12 H12A 1.003(18)
C7 C6 1.380(2)
C7 H7A 0.948(19)
C9 C10 1.510(2)
C9 H9B 0.970(19)
C9 H9A 1.06(2)
C16 C15 1.523(2)
C16 H16B 0.976(17)
C16 H16A 0.978(18)
C10 H10B 0.97(2)
C10 H10A 0.933(18)
C15 C14 1.525(2)
C15 H15B 0.995(19)
C15 H15A 1.00(2)
C5 C6 1.366(2)
C5 C4 1.370(3)
C5 H5A 0.96(2)
C6 H6A 0.93(2)
C3 C4 1.382(2)
C3 H3A 0.905(19)
C13 C14 1.505(3)
C13 H13B 0.984(18)
C13 H13A 0.96(2)
C14 H14B 0.98(2)
C14 H14A 1.01(2)
C4 H4A 0.94(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652507
2 PubChem 90671453
