#------------------------------------------------------------------------------
#$Date: 2020-07-24 07:44:18 +0300 (Fri, 24 Jul 2020) $
#$Revision: 254538 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022200.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_2022200
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_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'-(4-methylbenzoyl)-5'H,7'H-spiro[cyclopentane-1,6'-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3'-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                104.763(17)
_cell_angle_beta                 100.147(15)
_cell_angle_gamma                103.858(17)
_cell_formula_units_Z            2
_cell_length_a                   9.1209(17)
_cell_length_b                   9.6732(19)
_cell_length_c                   11.958(2)
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.76
_cell_volume                     958.4(3)
_computing_cell_refinement
;
FRAMBO (Bruker, 2009)
;
_computing_data_collection
;
FRAMBO (Bruker, 2009)
;
_computing_data_reduction
;
SHELXTL (Bruker, 2000)
;
_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
;
olex2.solve (Bourhis et al., 2015)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8686
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.03775
_exptl_absorpt_correction_T_min  0.95732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0417
_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)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                2037
_reflns_number_total             3842
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fm3064sup1.cif
_cod_data_source_block           I
_cod_database_code               2022200
_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.
;
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.11874(7) 0.35535(6) 0.31730(5) 0.04464(19) Uani d 1 . .
N N3 0.2652(2) 0.59934(17) 0.26016(14) 0.0411(4) Uani d 1 . .
N N4 0.1350(2) 0.64544(16) 0.22494(14) 0.0419(4) Uani d 1 . .
H H4 0.101492 0.601422 0.134228 0.050 Uiso d 1 . .
O O1 0.41191(19) 0.28613(16) 0.38001(13) 0.0595(4) Uani d 1 . .
C C4 -0.0408(2) 0.4147(2) 0.24743(17) 0.0381(5) Uani d 1 . .
H H4A -0.120437 0.385988 0.292629 0.046 Uiso d 1 . .
O O2 0.6474(2) 0.40289(18) 0.36494(16) 0.0718(5) Uani d 1 . .
O O3 -0.0416(2) 0.36910(16) 0.04306(13) 0.0814(6) Uani d 1 . .
C C6 -0.1853(3) 0.1605(2) 0.08551(18) 0.0428(5) Uani d 1 . .
C C3 0.0039(3) 0.5855(2) 0.27300(18) 0.0401(5) Uani d 1 . .
C C1 0.2740(3) 0.4807(2) 0.29763(16) 0.0380(5) Uani d 1 . .
N N2 0.4072(2) 0.68261(19) 0.25891(16) 0.0532(5) Uani d 1 . .
N N1 0.5076(2) 0.6166(2) 0.29365(17) 0.0567(5) Uani d 1 . .
C C5 -0.0883(3) 0.3188(2) 0.11743(18) 0.0477(6) Uani d 1 . .
C C16 0.0406(3) 0.6683(2) 0.40761(18) 0.0491(6) Uani d 1 . .
H H16A 0.003856 0.599086 0.449901 0.059 Uiso calc 1 . .
H H16B 0.152176 0.714255 0.440283 0.059 Uiso calc 1 . .
C C2 0.4315(3) 0.4941(2) 0.31995(18) 0.0442(6) Uani d 1 . .
C C13 0.5124(3) 0.3939(2) 0.35769(19) 0.0500(6) Uani d 1 . .
C C19 -0.1307(3) 0.6353(2) 0.2181(2) 0.0543(6) Uani d 1 . .
H H19A -0.128684 0.635789 0.137327 0.065 Uiso calc 1 . .
H H19B -0.230308 0.569130 0.215974 0.065 Uiso calc 1 . .
C C9 -0.3552(3) -0.1424(2) 0.0197(2) 0.0538(6) Uani d 1 . .
C C11 -0.2743(3) 0.1071(2) 0.1555(2) 0.0548(6) Uani d 1 . .
H H11 -0.277717 0.172522 0.226352 0.066 Uiso calc 1 . .
C C10 -0.3586(3) -0.0417(2) 0.1221(2) 0.0601(7) Uani d 1 . .
H H10 -0.419297 -0.074697 0.170471 0.072 Uiso calc 1 . .
C C7 -0.1838(3) 0.0602(3) -0.0197(2) 0.0669(8) Uani d 1 . .
H H7 -0.127390 0.093846 -0.070222 0.080 Uiso calc 1 . .
C C12 -0.4474(3) -0.3062(2) -0.0144(2) 0.0762(8) Uani d 1 . .
H H12A -0.487335 -0.324810 0.051173 0.114 Uiso calc 1 . .
H H12B -0.380675 -0.367180 -0.033165 0.114 Uiso calc 1 . .
H H12C -0.532739 -0.330427 -0.082948 0.114 Uiso calc 1 . .
C C14 0.4675(3) 0.1682(3) 0.4071(3) 0.0756(8) Uani d 1 . .
H H14A 0.521152 0.130667 0.348304 0.091 Uiso calc 1 . .
H H14B 0.540784 0.206663 0.485161 0.091 Uiso calc 1 . .
C C8 -0.2656(3) -0.0892(3) -0.0500(2) 0.0719(8) Uani d 1 . .
H H8 -0.259940 -0.155680 -0.119493 0.086 Uiso calc 1 . .
C C18 -0.1049(3) 0.7919(3) 0.2988(2) 0.0713(8) Uani d 1 . .
H H18A -0.030864 0.865374 0.278094 0.086 Uiso calc 1 . .
H H18B -0.202171 0.817029 0.293947 0.086 Uiso calc 1 . .
C C17 -0.0417(4) 0.7849(3) 0.4199(2) 0.0914(10) Uani d 1 . .
H H17A -0.126059 0.759870 0.457539 0.110 Uiso calc 1 . .
H H17B 0.030244 0.881408 0.469485 0.110 Uiso calc 1 . .
C C15 0.3388(4) 0.0503(3) 0.4058(4) 0.1248(14) Uani d 1 . .
H H15A 0.375739 -0.027836 0.425164 0.187 Uiso calc 1 . .
H H15B 0.268026 0.010891 0.327765 0.187 Uiso calc 1 . .
H H15C 0.285693 0.088182 0.463689 0.187 Uiso calc 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 . . 99.09(9) ?
C1 N3 N4 . . 129.70(17) ?
C1 N3 N2 . . 111.99(17) ?
N2 N3 N4 . . 118.31(15) ?
N3 N4 H4 . . 105.0 ?
N3 N4 C3 . . 112.38(14) ?
C3 N4 H4 . . 108.3 ?
C13 O1 C14 . . 117.3(2) ?
S1 C4 H4A . . 100.7 ?
C3 C4 S1 . . 112.18(14) ?
C3 C4 H4A . . 108.1 ?
C5 C4 S1 . . 104.56(13) ?
C5 C4 H4A . . 113.0 ?
C5 C4 C3 . . 117.07(15) ?
C11 C6 C5 . . 123.79(19) ?
C11 C6 C7 . . 118.0(2) ?
C7 C6 C5 . . 118.2(2) ?
N4 C3 C4 . . 113.75(15) ?
N4 C3 C16 . . 109.63(18) ?
N4 C3 C19 . . 105.38(15) ?
C4 C3 C16 . . 111.48(15) ?
C19 C3 C4 . . 112.14(18) ?
C19 C3 C16 . . 103.83(17) ?
N3 C1 S1 . . 124.99(16) ?
N3 C1 C2 . . 103.18(17) ?
C2 C1 S1 . . 131.74(16) ?
N1 N2 N3 . . 106.66(15) ?
N2 N1 C2 . . 109.1(2) ?
O3 C5 C4 . . 120.18(19) ?
O3 C5 C6 . . 121.28(19) ?
C6 C5 C4 . . 118.46(17) ?
C3 C16 H16A . . 110.4 ?
C3 C16 H16B . . 110.4 ?
H16A C16 H16B . . 108.6 ?
C17 C16 C3 . . 106.58(18) ?
C17 C16 H16A . . 110.4 ?
C17 C16 H16B . . 110.4 ?
C1 C2 C13 . . 128.8(2) ?
N1 C2 C1 . . 109.02(19) ?
N1 C2 C13 . . 122.0(2) ?
O1 C13 C2 . . 109.6(2) ?
O2 C13 O1 . . 124.2(2) ?
O2 C13 C2 . . 126.2(2) ?
C3 C19 H19A . . 110.8 ?
C3 C19 H19B . . 110.8 ?
H19A C19 H19B . . 108.8 ?
C18 C19 C3 . . 104.97(19) ?
C18 C19 H19A . . 110.8 ?
C18 C19 H19B . . 110.8 ?
C10 C9 C12 . . 120.7(2) ?
C10 C9 C8 . . 117.5(2) ?
C8 C9 C12 . . 121.8(2) ?
C6 C11 H11 . . 119.6 ?
C6 C11 C10 . . 120.9(2) ?
C10 C11 H11 . . 119.6 ?
C9 C10 C11 . . 121.6(2) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C6 C7 H7 . . 119.9 ?
C8 C7 C6 . . 120.3(2) ?
C8 C7 H7 . . 119.9 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C14 H14A . . 109.8 ?
O1 C14 H14B . . 109.8 ?
H14A C14 H14B . . 108.3 ?
C15 C14 O1 . . 109.3(2) ?
C15 C14 H14A . . 109.8 ?
C15 C14 H14B . . 109.8 ?
C9 C8 C7 . . 121.7(2) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
C19 C18 H18A . . 111.1 ?
C19 C18 H18B . . 111.1 ?
H18A C18 H18B . . 109.0 ?
C17 C18 C19 . . 103.51(18) ?
C17 C18 H18A . . 111.1 ?
C17 C18 H18B . . 111.1 ?
C16 C17 H17A . . 110.0 ?
C16 C17 H17B . . 110.0 ?
C18 C17 C16 . . 108.5(2) ?
C18 C17 H17A . . 110.0 ?
C18 C17 H17B . . 110.0 ?
H17A C17 H17B . . 108.4 ?
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 ?
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 . 1.834(2) ?
S1 C1 . 1.724(2) ?
N3 N4 . 1.400(2) ?
N3 C1 . 1.348(2) ?
N3 N2 . 1.356(2) ?
N4 H4 . 1.0182 ?
N4 C3 . 1.475(2) ?
O1 C13 . 1.329(3) ?
O1 C14 . 1.439(2) ?
C4 H4A . 1.0074 ?
C4 C3 . 1.538(3) ?
C4 C5 . 1.517(3) ?
O2 C13 . 1.200(3) ?
O3 C5 . 1.210(2) ?
C6 C5 . 1.486(3) ?
C6 C11 . 1.372(3) ?
C6 C7 . 1.384(3) ?
C3 C16 . 1.539(3) ?
C3 C19 . 1.527(3) ?
C1 C2 . 1.382(3) ?
N2 N1 . 1.304(2) ?
N1 C2 . 1.363(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C16 C17 . 1.489(3) ?
C2 C13 . 1.461(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 C18 . 1.512(3) ?
C9 C10 . 1.367(3) ?
C9 C12 . 1.515(3) ?
C9 C8 . 1.373(3) ?
C11 H11 . 0.9300 ?
C11 C10 . 1.376(3) ?
C10 H10 . 0.9300 ?
C7 H7 . 0.9300 ?
C7 C8 . 1.377(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.423(4) ?
C8 H8 . 0.9300 ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C18 C17 . 1.487(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S1 C4 C3 N4 . . . . 62.33(19) ?
S1 C4 C3 C16 . . . . -62.3(2) ?
S1 C4 C3 C19 . . . . -178.20(14) ?
S1 C4 C5 O3 . . . . -99.3(2) ?
S1 C4 C5 C6 . . . . 77.3(2) ?
S1 C1 C2 N1 . . . . -177.44(15) ?
S1 C1 C2 C13 . . . . 6.5(3) ?
N3 N4 C3 C4 . . . . -52.2(2) ?
N3 N4 C3 C16 . . . . 73.37(18) ?
N3 N4 C3 C19 . . . . -175.44(15) ?
N3 C1 C2 N1 . . . . -0.8(2) ?
N3 C1 C2 C13 . . . . -176.89(19) ?
N3 N2 N1 C2 . . . . -1.5(2) ?
N4 N3 C1 S1 . . . . -2.8(3) ?
N4 N3 C1 C2 . . . . -179.70(17) ?
N4 N3 N2 N1 . . . . -179.33(16) ?
N4 C3 C16 C17 . . . . 98.7(2) ?
N4 C3 C19 C18 . . . . -84.7(2) ?
C4 S1 C1 N3 . . . . 10.11(18) ?
C4 S1 C1 C2 . . . . -173.91(19) ?
C4 C3 C16 C17 . . . . -134.4(2) ?
C4 C3 C19 C18 . . . . 151.00(18) ?
C6 C11 C10 C9 . . . . 1.0(4) ?
C6 C7 C8 C9 . . . . 2.6(4) ?
C3 C4 C5 O3 . . . . 25.5(3) ?
C3 C4 C5 C6 . . . . -157.87(19) ?
C3 C16 C17 C18 . . . . -8.8(3) ?
C3 C19 C18 C17 . . . . -36.0(3) ?
C1 S1 C4 C3 . . . . -37.08(15) ?
C1 S1 C4 C5 . . . . 90.78(14) ?
C1 N3 N4 C3 . . . . 21.9(3) ?
C1 N3 N2 N1 . . . . 1.0(2) ?
C1 C2 C13 O1 . . . . -5.8(3) ?
C1 C2 C13 O2 . . . . 172.4(2) ?
N2 N3 N4 C3 . . . . -157.68(16) ?
N2 N3 C1 S1 . . . . 176.81(14) ?
N2 N3 C1 C2 . . . . -0.1(2) ?
N2 N1 C2 C1 . . . . 1.5(2) ?
N2 N1 C2 C13 . . . . 177.90(18) ?
N1 C2 C13 O1 . . . . 178.64(18) ?
N1 C2 C13 O2 . . . . -3.2(3) ?
C5 C4 C3 N4 . . . . -58.6(2) ?
C5 C4 C3 C16 . . . . 176.86(19) ?
C5 C4 C3 C19 . . . . 60.9(2) ?
C5 C6 C11 C10 . . . . -178.3(2) ?
C5 C6 C7 C8 . . . . 176.7(2) ?
C16 C3 C19 C18 . . . . 30.5(2) ?
C13 O1 C14 C15 . . . . -169.0(2) ?
C19 C3 C16 C17 . . . . -13.5(2) ?
C19 C18 C17 C16 . . . . 27.8(3) ?
C11 C6 C5 C4 . . . . 20.9(3) ?
C11 C6 C5 O3 . . . . -162.5(2) ?
C11 C6 C7 C8 . . . . -2.2(4) ?
C10 C9 C8 C7 . . . . -1.1(4) ?
C7 C6 C5 C4 . . . . -157.9(2) ?
C7 C6 C5 O3 . . . . 18.8(3) ?
C7 C6 C11 C10 . . . . 0.4(4) ?
C12 C9 C10 C11 . . . . 179.2(2) ?
C12 C9 C8 C7 . . . . 179.0(3) ?
C14 O1 C13 O2 . . . . -4.1(3) ?
C14 O1 C13 C2 . . . . 174.04(18) ?
C8 C9 C10 C11 . . . . -0.7(4) ?

_cod_database_fobs_code 2022200
