#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/73/4507320.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_4507320
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 Cl N2 S'
_chemical_formula_weight         294.83
_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                 104.4230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7995(7)
_cell_length_b                   15.1263(9)
_cell_length_c                   7.9069(5)
_cell_measurement_reflns_used    4499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.72
_cell_measurement_theta_min      2.69
_cell_volume                     1482.60(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0241
_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       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12273
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.9301
_exptl_absorpt_correction_T_min  0.8301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.091(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0450
_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)+(0.0480P)²+0.3536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2699
_reflns_number_total             3227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg301511x_si_008.cif
_cod_data_source_block           CCDC_894495
_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               4507320
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
S1 S 0.86734(3) 0.15743(3) 0.10739(5) 0.04792(16) Uani 1 1 d
Cl1 Cl 1.42980(4) 0.38722(4) -0.07598(8) 0.0700(2) Uani 1 1 d
N1 N 1.02406(10) 0.25130(9) 0.05483(19) 0.0405(3) Uani 1 1 d
C1 C 1.11959(11) 0.28070(10) 0.01630(18) 0.0344(3) Uani 1 1 d
C7 C 0.96011(11) 0.18231(10) -0.02040(19) 0.0351(3) Uani 1 1 d
N2 N 0.97024(10) 0.14562(8) -0.15990(17) 0.0377(3) Uani 1 1 d
C10 C 0.77393(12) 0.08392(10) -0.0423(2) 0.0382(3) Uani 1 1 d
C4 C 1.31104(12) 0.34521(11) -0.0377(2) 0.0428(4) Uani 1 1 d
C5 C 1.28454(12) 0.25785(12) -0.0713(2) 0.0442(4) Uani 1 1 d
C2 C 1.14724(13) 0.36898(11) 0.0472(2) 0.0416(4) Uani 1 1 d
C9 C 0.84276(14) 0.02335(11) -0.1236(3) 0.0450(4) Uani 1 1 d
C3 C 1.24323(14) 0.40122(11) 0.0222(2) 0.0454(4) Uani 1 1 d
C8 C 0.90416(15) 0.07047(12) -0.2378(2) 0.0472(4) Uani 1 1 d
C15 C 0.71543(14) 0.02994(12) 0.0695(3) 0.0485(4) Uani 1 1 d
C6 C 1.18945(12) 0.22541(11) -0.0424(2) 0.0406(4) Uani 1 1 d
C11 C 0.69241(16) 0.13675(13) -0.1788(2) 0.0507(4) Uani 1 1 d
C14 C 0.63935(15) 0.08465(14) 0.1474(3) 0.0547(5) Uani 1 1 d
C12 C 0.61345(17) 0.18952(15) -0.1030(3) 0.0609(5) Uani 1 1 d
C13 C 0.55787(15) 0.13278(16) 0.0065(3) 0.0621(5) Uani 1 1 d
H5A H 1.3291(16) 0.2222(12) -0.115(2) 0.053(5) Uiso 1 1 d
H6A H 1.1717(15) 0.1653(13) -0.066(2) 0.046(5) Uiso 1 1 d
H9A H 0.7958(15) -0.0202(12) -0.194(2) 0.050(5) Uiso 1 1 d
H15A H 0.7675(15) -0.0005(13) 0.159(2) 0.052(5) Uiso 1 1 d
H8A H 0.9518(16) 0.0269(13) -0.272(3) 0.058(5) Uiso 1 1 d
H11B H 0.6544(16) 0.0956(13) -0.260(3) 0.055(5) Uiso 1 1 d
H8B H 0.8549(15) 0.0911(13) -0.344(3) 0.050(5) Uiso 1 1 d
H14B H 0.6775(15) 0.1258(12) 0.228(3) 0.046(5) Uiso 1 1 d
H14A H 0.6083(18) 0.0467(15) 0.221(3) 0.071(6) Uiso 1 1 d
H12B H 0.6538(16) 0.2365(14) -0.030(3) 0.062(6) Uiso 1 1 d
H15B H 0.6716(16) -0.0168(14) -0.008(3) 0.062(6) Uiso 1 1 d
H13B H 0.5141(18) 0.0900(15) -0.065(3) 0.064(6) Uiso 1 1 d
H12A H 0.562(2) 0.2140(15) -0.197(3) 0.078(7) Uiso 1 1 d
H9B H 0.8938(16) -0.0099(14) -0.025(3) 0.058(5) Uiso 1 1 d
H3A H 1.2629(16) 0.4621(13) 0.044(2) 0.055(5) Uiso 1 1 d
H11A H 0.7291(17) 0.1765(15) -0.244(3) 0.068(6) Uiso 1 1 d
H13A H 0.509(2) 0.1685(15) 0.050(3) 0.076(7) Uiso 1 1 d
H1A H 1.0067(15) 0.2783(12) 0.135(3) 0.051(5) Uiso 1 1 d
H2A H 1.1024(15) 0.4073(12) 0.083(2) 0.046(5) 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'
Cl Cl 0.1484 0.1585 '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 100.48(7)
C7 N1 C1 127.35(13)
C7 N1 H1A 117.6(13)
C1 N1 H1A 115.0(13)
C6 C1 C2 118.82(14)
C6 C1 N1 123.42(14)
C2 C1 N1 117.68(13)
N2 C7 N1 122.12(13)
N2 C7 S1 128.85(12)
N1 C7 S1 109.03(11)
C7 N2 C8 122.24(13)
C9 C10 C11 112.48(14)
C9 C10 C15 109.96(13)
C11 C10 C15 109.96(14)
C9 C10 S1 106.56(11)
C11 C10 S1 111.09(12)
C15 C10 S1 106.58(12)
C5 C4 C3 120.73(15)
C5 C4 Cl1 120.11(13)
C3 C4 Cl1 119.13(13)
C4 C5 C6 119.65(15)
C4 C5 H5A 119.6(12)
C6 C5 H5A 120.7(12)
C3 C2 C1 120.78(15)
C3 C2 H2A 118.1(12)
C1 C2 H2A 121.1(12)
C8 C9 C10 114.20(14)
C8 C9 H9A 108.5(11)
C10 C9 H9A 108.1(11)
C8 C9 H9B 111.1(11)
C10 C9 H9B 107.7(11)
H9A C9 H9B 107.0(15)
C4 C3 C2 119.40(15)
C4 C3 H3A 119.6(12)
C2 C3 H3A 121.0(12)
N2 C8 C9 116.58(14)
N2 C8 H8A 107.8(11)
C9 C8 H8A 107.3(12)
N2 C8 H8B 107.4(11)
C9 C8 H8B 110.2(11)
H8A C8 H8B 107.3(16)
C14 C15 C10 113.50(15)
C14 C15 H15A 110.9(11)
C10 C15 H15A 109.5(11)
C14 C15 H15B 108.2(11)
C10 C15 H15B 107.5(12)
H15A C15 H15B 106.9(16)
C5 C6 C1 120.59(15)
C5 C6 H6A 119.3(11)
C1 C6 H6A 120.1(11)
C12 C11 C10 113.58(16)
C12 C11 H11B 109.6(12)
C10 C11 H11B 106.4(12)
C12 C11 H11A 109.6(13)
C10 C11 H11A 111.1(12)
H11B C11 H11A 106.2(18)
C13 C14 C15 110.98(17)
C13 C14 H14B 109.1(11)
C15 C14 H14B 111.0(12)
C13 C14 H14A 114.6(13)
C15 C14 H14A 108.7(13)
H14B C14 H14A 102.1(17)
C13 C12 C11 112.32(17)
C13 C12 H12B 109.1(13)
C11 C12 H12B 108.0(12)
C13 C12 H12A 110.0(15)
C11 C12 H12A 107.4(15)
H12B C12 H12A 110.0(19)
C14 C13 C12 110.99(16)
C14 C13 H13B 108.0(13)
C12 C13 H13B 109.8(13)
C14 C13 H13A 113.7(14)
C12 C13 H13A 109.2(14)
H13B C13 H13A 105.0(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.7805(14)
S1 C10 1.8334(15)
Cl1 C4 1.7419(16)
N1 C7 1.3675(19)
N1 C1 1.4040(19)
N1 H1A 0.83(2)
C1 C6 1.386(2)
C1 C2 1.387(2)
C7 N2 1.2699(19)
N2 C8 1.459(2)
C10 C9 1.520(2)
C10 C11 1.527(2)
C10 C15 1.529(2)
C4 C5 1.374(2)
C4 C3 1.379(2)
C5 C6 1.383(2)
C5 H5A 0.91(2)
C2 C3 1.381(2)
C2 H2A 0.908(19)
C9 C8 1.515(2)
C9 H9A 0.968(19)
C9 H9B 1.02(2)
C3 H3A 0.96(2)
C8 H8A 0.98(2)
C8 H8B 0.965(19)
C15 C14 1.520(3)
C15 H15A 0.962(19)
C15 H15B 1.01(2)
C6 H6A 0.945(19)
C11 C12 1.523(3)
C11 H11B 0.94(2)
C11 H11A 0.99(2)
C14 C13 1.510(3)
C14 H14B 0.935(19)
C14 H14A 0.97(2)
C12 C13 1.517(3)
C12 H12B 0.98(2)
C12 H12A 0.93(2)
C13 H13B 0.95(2)
C13 H13A 0.95(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652510
2 PubChem 90671465
