#------------------------------------------------------------------------------
#$Date: 2020-07-24 07:44:18 +0300 (Fri, 24 Jul 2020) $
#$Revision: 254538 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022202.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022202
loop_
_publ_author_name
'Obydennov, Konstantin L'vovich'
'Kalinina, Tatiana Andreevna'
'Vysokova, Olga Alexandrovna'
'Slepukhin, Pavel Alexandrovich'
'Pozdina, Varvara Alexandrovna'
'Ulitko, Maria Valer'evna'
'Glukhareva, Tatiana Vladimirovna'
_publ_section_title
;
 The different modes of chiral
 [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines: crystal packing,
 conformation investigation and cellular activity
;
_journal_coeditor_code           FM3064
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620009328
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C19 H22 N4 O3 S'
_chemical_formula_moiety         'C19 H22 N4 O3 S'
_chemical_formula_sum            'C19 H22 N4 O3 S'
_chemical_formula_weight         386.46
_chemical_name_systematic
'Ethyl 5'-benzoyl-5'H,7'H-spiro[cyclohexane-1,6'-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3'-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.799(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8289(6)
_cell_length_b                   18.0940(18)
_cell_length_c                   9.0173(8)
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      3.20
_cell_volume                     946.17(16)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2020) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6254
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_min         3.198
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details
;
Flack x determined using 908 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0180P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                2544
_reflns_number_total             4285
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fm3064sup1.cif
_cod_data_source_block           III
_cod_database_code               2022202
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.36652(11) 0.60607(4) 0.42819(7) 0.05628(19) Uani d 1 . .
N N4 0.7935(4) 0.72176(13) 0.4776(2) 0.0508(5) Uani d 1 . .
O O2 0.2896(3) 0.62515(12) -0.08442(19) 0.0837(6) Uani d 1 . .
C C11 0.8701(5) 0.44206(18) 0.6728(3) 0.0716(9) Uani d 1 . .
H H11 0.997368 0.451200 0.621087 0.086 Uiso calc 1 . .
N N3 0.6869(3) 0.70046(11) 0.3383(2) 0.0483(5) Uani d 1 . .
O O3 0.9198(4) 0.57769(12) 0.5526(3) 0.1050(8) Uani d 1 . .
C C10 0.8512(7) 0.37557(19) 0.7430(5) 0.0943(12) Uani d 1 . .
H H10 0.966230 0.340088 0.740841 0.113 Uiso calc 1 . .
N N2 0.7662(4) 0.73095(12) 0.2163(3) 0.0592(6) Uani d 1 . .
O O1 0.1707(3) 0.58020(10) 0.12459(19) 0.0687(6) Uani d 1 . .
C C9 0.6622(8) 0.36191(19) 0.8160(4) 0.0957(12) Uani d 1 . .
H H9 0.649362 0.316911 0.864339 0.115 Uiso calc 1 . .
N N1 0.6394(4) 0.70367(13) 0.1026(2) 0.0622(6) Uani d 1 . .
C C8 0.4936(6) 0.41267(18) 0.8193(3) 0.0800(9) Uani d 1 . .
H H8 0.364350 0.402166 0.868084 0.096 Uiso calc 1 . .
C C7 0.5123(5) 0.48037(14) 0.7501(3) 0.0589(7) Uani d 1 . .
H H7 0.395967 0.515363 0.752823 0.071 Uiso calc 1 . .
C C6 0.7023(5) 0.49584(14) 0.6778(3) 0.0499(6) Uani d 1 . .
C C5 0.7399(5) 0.56704(15) 0.6064(3) 0.0529(7) Uani d 1 . .
C C14 -0.0157(5) 0.5406(2) 0.0433(3) 0.0818(9) Uani d 1 . .
H H14A 0.044129 0.505773 -0.024936 0.098 Uiso calc 1 . .
H H14B -0.117890 0.574749 -0.013907 0.098 Uiso calc 1 . .
C C15 -0.1415(5) 0.50110(19) 0.1526(4) 0.0909(11) Uani d 1 . .
H H15A -0.267320 0.474084 0.101443 0.136 Uiso calc 1 . .
H H15B -0.038924 0.467386 0.208389 0.136 Uiso calc 1 . .
H H15C -0.200264 0.536072 0.219372 0.136 Uiso calc 1 . .
C C19 0.8007(4) 0.71901(17) 0.7426(3) 0.0602(7) Uani d 1 . .
H H19A 0.720747 0.700856 0.824554 0.072 Uiso calc 1 . .
H H19B 0.940185 0.689966 0.740126 0.072 Uiso calc 1 . .
C C12 0.8676(5) 0.79896(18) 0.7729(3) 0.0774(9) Uani d 1 . .
H H12A 0.954194 0.802957 0.870237 0.093 Uiso calc 1 . .
H H12B 0.965394 0.815854 0.698876 0.093 Uiso calc 1 . .
C C18 0.6552(6) 0.84698(17) 0.7678(4) 0.0833(10) Uani d 1 . .
H H18A 0.700099 0.898134 0.784989 0.100 Uiso calc 1 . .
H H18B 0.561634 0.832065 0.845682 0.100 Uiso calc 1 . .
C C17 0.5169(5) 0.83971(15) 0.6174(3) 0.0697(8) Uani d 1 . .
H H17A 0.380600 0.870654 0.614750 0.084 Uiso calc 1 . .
H H17B 0.608726 0.856651 0.540201 0.084 Uiso calc 1 . .
C C16 0.4458(4) 0.76090(13) 0.5875(3) 0.0514(7) Uani d 1 . .
H H16A 0.364179 0.757671 0.488446 0.062 Uiso calc 1 . .
H H16B 0.339679 0.746261 0.658346 0.062 Uiso calc 1 . .
C C3 0.6485(4) 0.70683(14) 0.5982(2) 0.0448(6) Uani d 1 . .
C C4 0.5561(4) 0.62651(13) 0.5941(2) 0.0448(6) Uani d 1 . .
H H4A 0.466012 0.620596 0.679352 0.054 Uiso calc 1 . .
C C13 0.3082(5) 0.62070(16) 0.0483(3) 0.0588(7) Uani d 1 . .
C C2 0.4797(5) 0.65724(14) 0.1501(2) 0.0501(6) Uani d 1 . .
C C1 0.5114(4) 0.65376(13) 0.3023(3) 0.0452(6) Uani d 1 . .
H H4 0.914(5) 0.6921(15) 0.495(3) 0.069(10) Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C4 . . 98.29(11) ?
N3 N4 C3 . . 112.22(18) ?
N3 N4 H4 . . 105.1(18) ?
C3 N4 H4 . . 105.4(17) ?
C10 C11 H11 . . 119.6 ?
C10 C11 C6 . . 120.8(3) ?
C6 C11 H11 . . 119.6 ?
N2 N3 N4 . . 117.4(2) ?
C1 N3 N4 . . 130.53(19) ?
C1 N3 N2 . . 112.0(2) ?
C11 C10 H10 . . 120.3 ?
C9 C10 C11 . . 119.3(3) ?
C9 C10 H10 . . 120.3 ?
N1 N2 N3 . . 105.9(2) ?
C13 O1 C14 . . 118.4(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 C10 . . 120.9(3) ?
C8 C9 H9 . . 119.5 ?
N2 N1 C2 . . 109.87(19) ?
C9 C8 H8 . . 119.9 ?
C9 C8 C7 . . 120.2(3) ?
C7 C8 H8 . . 119.9 ?
C8 C7 H7 . . 120.0 ?
C6 C7 C8 . . 120.0(3) ?
C6 C7 H7 . . 120.0 ?
C11 C6 C5 . . 117.8(3) ?
C7 C6 C11 . . 118.7(3) ?
C7 C6 C5 . . 123.5(2) ?
O3 C5 C6 . . 119.2(2) ?
O3 C5 C4 . . 119.4(2) ?
C6 C5 C4 . . 121.3(2) ?
O1 C14 H14A . . 110.2 ?
O1 C14 H14B . . 110.2 ?
O1 C14 C15 . . 107.6(2) ?
H14A C14 H14B . . 108.5 ?
C15 C14 H14A . . 110.2 ?
C15 C14 H14B . . 110.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
H19A C19 H19B . . 107.6 ?
C12 C19 H19A . . 108.7 ?
C12 C19 H19B . . 108.7 ?
C12 C19 C3 . . 114.3(2) ?
C3 C19 H19A . . 108.7 ?
C3 C19 H19B . . 108.7 ?
C19 C12 H12A . . 109.6 ?
C19 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C18 C12 C19 . . 110.4(2) ?
C18 C12 H12A . . 109.6 ?
C18 C12 H12B . . 109.6 ?
C12 C18 H18A . . 109.7 ?
C12 C18 H18B . . 109.7 ?
C12 C18 C17 . . 109.8(3) ?
H18A C18 H18B . . 108.2 ?
C17 C18 H18A . . 109.7 ?
C17 C18 H18B . . 109.7 ?
C18 C17 H17A . . 109.5 ?
C18 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.1 ?
C16 C17 C18 . . 110.9(2) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
C17 C16 H16A . . 108.9 ?
C17 C16 H16B . . 108.9 ?
C17 C16 C3 . . 113.5(2) ?
H16A C16 H16B . . 107.7 ?
C3 C16 H16A . . 108.9 ?
C3 C16 H16B . . 108.9 ?
N4 C3 C19 . . 106.19(19) ?
N4 C3 C16 . . 109.5(2) ?
N4 C3 C4 . . 112.32(18) ?
C19 C3 C16 . . 110.0(2) ?
C19 C3 C4 . . 109.21(19) ?
C16 C3 C4 . . 109.50(19) ?
S1 C4 H4A . . 107.2 ?
C5 C4 S1 . . 106.53(16) ?
C5 C4 C3 . . 115.02(19) ?
C5 C4 H4A . . 107.2 ?
C3 C4 S1 . . 113.23(15) ?
C3 C4 H4A . . 107.2 ?
O2 C13 O1 . . 123.9(3) ?
O2 C13 C2 . . 126.3(3) ?
O1 C13 C2 . . 109.8(2) ?
N1 C2 C13 . . 122.4(2) ?
N1 C2 C1 . . 108.6(2) ?
C1 C2 C13 . . 129.0(2) ?
N3 C1 S1 . . 124.85(18) ?
N3 C1 C2 . . 103.7(2) ?
C2 C1 S1 . . 131.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 . 1.806(2) ?
S1 C1 . 1.715(2) ?
N4 N3 . 1.398(3) ?
N4 C3 . 1.468(3) ?
N4 H4 . 0.88(3) ?
O2 C13 . 1.194(3) ?
C11 H11 . 0.9300 ?
C11 C10 . 1.369(4) ?
C11 C6 . 1.383(4) ?
N3 N2 . 1.353(3) ?
N3 C1 . 1.341(3) ?
O3 C5 . 1.214(3) ?
C10 H10 . 0.9300 ?
C10 C9 . 1.362(5) ?
N2 N1 . 1.300(3) ?
O1 C14 . 1.439(3) ?
O1 C13 . 1.328(3) ?
C9 H9 . 0.9300 ?
C9 C8 . 1.348(4) ?
N1 C2 . 1.355(3) ?
C8 H8 . 0.9300 ?
C8 C7 . 1.384(4) ?
C7 H7 . 0.9300 ?
C7 C6 . 1.370(4) ?
C6 C5 . 1.467(4) ?
C5 C4 . 1.515(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.472(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 C12 . 1.516(4) ?
C19 C3 . 1.516(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 C18 . 1.509(4) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C18 C17 . 1.512(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 C16 . 1.502(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C16 C3 . 1.530(3) ?
C3 C4 . 1.549(3) ?
C4 H4A . 0.9800 ?
C13 C2 . 1.447(4) ?
C2 C1 . 1.368(3) ?

_cod_database_fobs_code 2022202
