#------------------------------------------------------------------------------
#$Date: 2020-06-28 07:52:45 +0300 (Sun, 28 Jun 2020) $
#$Revision: 253533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022173.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_2022173
loop_
_publ_author_name
'Bond, Andrew D.'
'Sun, Changquan C.'
_publ_section_title
;
 Intermolecular interactions and disorder in six isostructural celecoxib
 solvates
;
_journal_coeditor_code           SK3751
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620008359
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C17 H14 F3 N3 O2 S, C5 H9 N O'
_chemical_formula_moiety         'C17 H14 F3 N3 O2 S, C5 H9 N O'
_chemical_formula_sum            'C22 H23 F3 N4 O3 S'
_chemical_formula_weight         480.50
_chemical_name_common
;
Celecoxib N-methyl-2-pyrrolidone monosolvate
;
_chemical_name_systematic
;
4-[5-(4-Methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
N-methylpyrrolidin-2-one monosolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 101.358(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9978(4)
_cell_length_b                   9.0896(3)
_cell_length_c                   21.9732(8)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.51
_cell_measurement_theta_min      3.76
_cell_volume                     2349.36(14)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24378
_diffrn_reflns_theta_full        66.791
_diffrn_reflns_theta_max         66.791
_diffrn_reflns_theta_min         3.758
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.240
_refine_ls_extinction_coef       0.0093(5)
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0475
_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)+(0.0683P)²+0.6367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3112
_reflns_number_total             4146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3751sup1.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022173
_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   0.726
_shelx_estimated_absorpt_t_max   0.748
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.42443(5) 0.72995(8) 0.57323(3) 0.0743(3) Uani d 1 . .
O O1 0.40662(15) 0.6918(3) 0.63344(9) 0.0970(6) Uani d 1 . .
O O2 0.37053(14) 0.8572(2) 0.54265(10) 0.0974(6) Uani d 1 . .
N N1 0.97465(15) 0.8705(2) 0.65213(9) 0.0718(5) Uani d 1 . .
N N2 0.92235(13) 0.8146(2) 0.59662(8) 0.0600(5) Uani d 1 . .
N N3 0.38435(16) 0.5916(3) 0.52861(10) 0.0796(6) Uani d 1 . .
H H1N 0.393(3) 0.614(3) 0.4911(7) 0.119 Uiso d 1 . .
H H2N 0.421(2) 0.514(2) 0.5457(12) 0.119 Uiso d 1 . .
C C1 1.08126(19) 0.8883(3) 0.64533(12) 0.0728(6) Uani d 1 . .
C C2 1.09811(18) 0.8453(3) 0.58771(12) 0.0687(6) Uani d 1 . .
H H2A 1.165852 0.848585 0.573206 0.082 Uiso calc 1 . .
C C3 0.99450(16) 0.7967(2) 0.55607(10) 0.0565(5) Uani d 1 . .
C C4 1.1659(3) 0.9471(4) 0.69872(16) 0.1011(10) Uani d 1 . .
F F1 1.2535(9) 0.994(2) 0.6765(5) 0.222(8) Uani d 0.507(13) A 1
F F3 1.1276(7) 1.0600(9) 0.7205(3) 0.134(3) Uani d 0.507(13) A 1
F F2 1.1967(14) 0.8585(8) 0.7407(5) 0.232(9) Uani d 0.507(13) A 1
F F1A 1.1958(8) 1.0844(6) 0.6935(7) 0.182(7) Uani d 0.493(13) A 2
F F2A 1.2593(4) 0.8749(8) 0.7101(3) 0.108(3) Uani d 0.493(13) A 2
F F3A 1.1318(6) 0.9433(19) 0.7522(4) 0.194(8) Uani d 0.493(13) A 2
C C5 0.96376(16) 0.7310(2) 0.49422(10) 0.0560(5) Uani d 1 . .
C C6 0.88572(16) 0.6174(2) 0.48013(11) 0.0590(5) Uani d 1 . .
H H6A 0.848432 0.582550 0.510538 0.071 Uiso calc 1 . .
C C7 0.86273(17) 0.5559(3) 0.42205(11) 0.0653(6) Uani d 1 . .
H H7A 0.809584 0.480362 0.413807 0.078 Uiso calc 1 . .
C C8 0.9163(2) 0.6029(3) 0.37558(12) 0.0733(6) Uani d 1 . .
C C9 0.9950(2) 0.7151(3) 0.38973(13) 0.0833(8) Uani d 1 . .
H H9A 1.033100 0.748272 0.359382 0.100 Uiso calc 1 . .
C C10 1.0182(2) 0.7789(3) 0.44766(12) 0.0733(7) Uani d 1 . .
H H10A 1.070912 0.854952 0.455685 0.088 Uiso calc 1 . .
C C11 0.8899(3) 0.5348(4) 0.31160(14) 0.1128(11) Uani d 1 . .
H H11A 0.935098 0.581327 0.285594 0.169 Uiso calc 1 . .
H H11B 0.907036 0.431568 0.314617 0.169 Uiso calc 1 . .
H H11C 0.810760 0.548188 0.293943 0.169 Uiso calc 1 . .
C C12 0.80263(16) 0.7899(2) 0.58845(10) 0.0561(5) Uani d 1 . .
C C13 0.76268(19) 0.7091(3) 0.63267(11) 0.0715(6) Uani d 1 . .
H H13A 0.813363 0.667305 0.665627 0.086 Uiso calc 1 . .
C C14 0.64752(19) 0.6904(3) 0.62788(11) 0.0740(7) Uani d 1 . .
H H14A 0.620015 0.635728 0.657536 0.089 Uiso calc 1 . .
C C15 0.57292(17) 0.7531(2) 0.57887(11) 0.0615(6) Uani d 1 . .
C C16 0.61338(17) 0.8324(2) 0.53439(10) 0.0597(5) Uani d 1 . .
H H16A 0.562852 0.873081 0.501098 0.072 Uiso calc 1 . .
C C17 0.72897(16) 0.8514(2) 0.53925(10) 0.0582(5) Uani d 1 . .
H H17A 0.756691 0.905349 0.509478 0.070 Uiso calc 1 . .
O O1S 0.46487(18) 0.6396(2) 0.41492(10) 0.0977(6) Uani d 0.679(8) B 1
N N1S 0.3890(4) 0.8101(5) 0.34400(18) 0.0848(14) Uani d 0.679(8) B 1
C C1S 0.4695(5) 0.7240(8) 0.3717(3) 0.0727(16) Uani d 0.679(8) B 1
C C2S 0.5661(7) 0.7546(11) 0.3406(4) 0.122(3) Uani d 0.679(8) B 1
H H2S1 0.624984 0.807865 0.368541 0.146 Uiso calc 0.679(8) B 1
H H2S2 0.598100 0.662814 0.329412 0.146 Uiso calc 0.679(8) B 1
C C3S 0.5277(6) 0.8373(13) 0.2880(4) 0.177(4) Uani d 0.679(8) B 1
H H3S1 0.520389 0.776555 0.251096 0.212 Uiso calc 0.679(8) B 1
H H3S2 0.580123 0.916926 0.284945 0.212 Uiso calc 0.679(8) B 1
C C4S 0.4020(6) 0.9032(9) 0.2952(4) 0.117(3) Uani d 0.679(8) B 1
H H4S1 0.405189 1.006227 0.306865 0.140 Uiso calc 0.679(8) B 1
H H4S2 0.343951 0.887895 0.258223 0.140 Uiso calc 0.679(8) B 1
C C5S 0.2769(6) 0.8127(10) 0.3636(4) 0.144(3) Uani d 0.679(8) B 1
H H5S1 0.227545 0.881874 0.338547 0.216 Uiso calc 0.679(8) B 1
H H5S2 0.243357 0.716451 0.358569 0.216 Uiso calc 0.679(8) B 1
H H5S3 0.287600 0.841352 0.406450 0.216 Uiso calc 0.679(8) B 1
O O1SA 0.46487(18) 0.6396(2) 0.41492(10) 0.0977(6) Uani d 0.321(8) B 2
N N1SA 0.4849(10) 0.7734(12) 0.3361(5) 0.129(4) Uani d 0.321(8) B 2
C C1SA 0.4263(10) 0.7305(16) 0.3763(6) 0.086(5) Uani d 0.321(8) B 2
C C2SA 0.3286(12) 0.8325(19) 0.3689(8) 0.127(6) Uani d 0.321(8) B 2
H H2S3 0.257860 0.777722 0.361922 0.152 Uiso calc 0.321(8) B 2
H H2S4 0.332888 0.891552 0.406092 0.152 Uiso calc 0.321(8) B 2
C C3SA 0.3331(13) 0.9204(19) 0.3193(8) 0.182(8) Uani d 0.321(8) B 2
H H3S3 0.326878 1.022754 0.330697 0.218 Uiso calc 0.321(8) B 2
H H3S4 0.270203 0.897681 0.285595 0.218 Uiso calc 0.321(8) B 2
C C4SA 0.4571(13) 0.8927(16) 0.2963(7) 0.096(4) Uani d 0.321(8) B 2
H H4S3 0.447513 0.866133 0.252777 0.116 Uiso calc 0.321(8) B 2
H H4S4 0.509558 0.974392 0.305894 0.116 Uiso calc 0.321(8) B 2
C C5SA 0.5910(16) 0.693(2) 0.3311(11) 0.151(8) Uani d 0.321(8) B 2
H H5S4 0.624693 0.737444 0.299464 0.227 Uiso calc 0.321(8) B 2
H H5S5 0.643550 0.697079 0.370117 0.227 Uiso calc 0.321(8) B 2
H H5S6 0.573025 0.591953 0.320419 0.227 Uiso calc 0.321(8) B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 . . 119.86(12) ?
O1 S1 N3 . . 107.11(12) ?
O2 S1 N3 . . 107.05(13) ?
O1 S1 C15 . . 107.24(11) ?
O2 S1 C15 . . 107.02(10) ?
N3 S1 C15 . . 108.11(11) ?
C1 N1 N2 . . 103.29(18) ?
N1 N2 C3 . . 112.96(16) ?
N1 N2 C12 . . 116.57(17) ?
C3 N2 C12 . . 130.41(18) ?
S1 N3 H1N . . 109(2) ?
S1 N3 H2N . . 108(2) ?
H1N N3 H2N . . 116.4(17) ?
N1 C1 C2 . . 112.9(2) ?
N1 C1 C4 . . 118.5(2) ?
C2 C1 C4 . . 128.6(2) ?
C3 C2 C1 . . 105.9(2) ?
C3 C2 H2A . . 127.0 ?
C1 C2 H2A . . 127.0 ?
N2 C3 C2 . . 105.0(2) ?
N2 C3 C5 . . 125.23(18) ?
C2 C3 C5 . . 129.7(2) ?
F2 C4 F3 . . 109.1(6) ?
F2A C4 F1A . . 105.2(4) ?
F2 C4 F1 . . 110.5(6) ?
F3 C4 F1 . . 104.7(6) ?
F2A C4 F3A . . 103.0(6) ?
F1A C4 F3A . . 104.0(6) ?
F2 C4 C1 . . 114.5(4) ?
F3 C4 C1 . . 110.4(4) ?
F2A C4 C1 . . 113.9(4) ?
F1A C4 C1 . . 115.4(5) ?
F1 C4 C1 . . 107.2(4) ?
F3A C4 C1 . . 114.1(4) ?
C6 C5 C10 . . 117.6(2) ?
C6 C5 C3 . . 123.13(19) ?
C10 C5 C3 . . 119.17(19) ?
C7 C6 C5 . . 121.0(2) ?
C7 C6 H6A . . 119.5 ?
C5 C6 H6A . . 119.5 ?
C6 C7 C8 . . 121.7(2) ?
C6 C7 H7A . . 119.1 ?
C8 C7 H7A . . 119.1 ?
C7 C8 C9 . . 117.4(2) ?
C7 C8 C11 . . 121.3(2) ?
C9 C8 C11 . . 121.3(2) ?
C10 C9 C8 . . 121.6(2) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C9 C10 C5 . . 120.7(2) ?
C9 C10 H10A . . 119.6 ?
C5 C10 H10A . . 119.6 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 120.86(19) ?
C17 C12 N2 . . 120.66(18) ?
C13 C12 N2 . . 118.40(19) ?
C14 C13 C12 . . 119.7(2) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C15 . . 119.7(2) ?
C13 C14 H14A . . 120.1 ?
C15 C14 H14A . . 120.1 ?
C16 C15 C14 . . 120.31(19) ?
C16 C15 S1 . . 120.12(17) ?
C14 C15 S1 . . 119.57(16) ?
C15 C16 C17 . . 120.0(2) ?
C15 C16 H16A . . 120.0 ?
C17 C16 H16A . . 120.0 ?
C12 C17 C16 . . 119.40(19) ?
C12 C17 H17A . . 120.3 ?
C16 C17 H17A . . 120.3 ?
C1S N1S C4S . . 122.7(5) ?
C1S N1S C5S . . 120.2(5) ?
C4S N1S C5S . . 117.1(6) ?
O1S C1S N1S . . 126.6(5) ?
O1S C1S C2S . . 129.1(5) ?
N1S C1S C2S . . 104.3(5) ?
C3S C2S C1S . . 109.1(7) ?
C3S C2S H2S1 . . 109.9 ?
C1S C2S H2S1 . . 109.9 ?
C3S C2S H2S2 . . 109.9 ?
C1S C2S H2S2 . . 109.9 ?
H2S1 C2S H2S2 . . 108.3 ?
C2S C3S C4S . . 106.1(6) ?
C2S C3S H3S1 . . 110.5 ?
C4S C3S H3S1 . . 110.5 ?
C2S C3S H3S2 . . 110.5 ?
C4S C3S H3S2 . . 110.5 ?
H3S1 C3S H3S2 . . 108.7 ?
N1S C4S C3S . . 95.5(5) ?
N1S C4S H4S1 . . 112.7 ?
C3S C4S H4S1 . . 112.7 ?
N1S C4S H4S2 . . 112.7 ?
C3S C4S H4S2 . . 112.7 ?
H4S1 C4S H4S2 . . 110.1 ?
N1S C5S H5S1 . . 109.5 ?
N1S C5S H5S2 . . 109.5 ?
H5S1 C5S H5S2 . . 109.5 ?
N1S C5S H5S3 . . 109.5 ?
H5S1 C5S H5S3 . . 109.5 ?
H5S2 C5S H5S3 . . 109.5 ?
C1SA N1SA C4SA . . 124.8(9) ?
C1SA N1SA C5SA . . 119.3(10) ?
C4SA N1SA C5SA . . 115.9(10) ?
O1SA C1SA N1SA . . 120.0(9) ?
O1SA C1SA C2SA . . 133.8(10) ?
N1SA C1SA C2SA . . 105.1(9) ?
C3SA C2SA C1SA . . 107.5(11) ?
C3SA C2SA H2S3 . . 110.2 ?
C1SA C2SA H2S3 . . 110.2 ?
C3SA C2SA H2S4 . . 110.2 ?
C1SA C2SA H2S4 . . 110.2 ?
H2S3 C2SA H2S4 . . 108.5 ?
C2SA C3SA C4SA . . 109.3(10) ?
C2SA C3SA H3S3 . . 109.8 ?
C4SA C3SA H3S3 . . 109.8 ?
C2SA C3SA H3S4 . . 109.8 ?
C4SA C3SA H3S4 . . 109.8 ?
H3S3 C3SA H3S4 . . 108.3 ?
N1SA C4SA C3SA . . 92.5(8) ?
N1SA C4SA H4S3 . . 113.2 ?
C3SA C4SA H4S3 . . 113.2 ?
N1SA C4SA H4S4 . . 113.2 ?
C3SA C4SA H4S4 . . 113.2 ?
H4S3 C4SA H4S4 . . 110.6 ?
N1SA C5SA H5S4 . . 109.5 ?
N1SA C5SA H5S5 . . 109.5 ?
H5S4 C5SA H5S5 . . 109.5 ?
N1SA C5SA H5S6 . . 109.5 ?
H5S4 C5SA H5S6 . . 109.5 ?
H5S5 C5SA H5S6 . . 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 O1 . 1.4240(18) ?
S1 O2 . 1.4271(18) ?
S1 N3 . 1.609(2) ?
S1 C15 . 1.774(2) ?
N1 C1 . 1.327(3) ?
N1 N2 . 1.356(2) ?
N2 C3 . 1.369(3) ?
N2 C12 . 1.430(2) ?
N3 H1N . 0.875(10) ?
N3 H2N . 0.875(10) ?
C1 C2 . 1.377(3) ?
C1 C4 . 1.492(4) ?
C2 C3 . 1.372(3) ?
C2 H2A . 0.9300 ?
C3 C5 . 1.464(3) ?
C4 F2 . 1.226(6) ?
C4 F3 . 1.258(5) ?
C4 F2A . 1.279(5) ?
C4 F1A . 1.310(6) ?
C4 F1 . 1.315(6) ?
C4 F3A . 1.320(7) ?
C5 C6 . 1.387(3) ?
C5 C10 . 1.388(3) ?
C6 C7 . 1.371(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.378(3) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.383(4) ?
C8 C11 . 1.512(4) ?
C9 C10 . 1.376(4) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.373(3) ?
C12 C13 . 1.377(3) ?
C13 C14 . 1.375(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.381(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.377(3) ?
C16 C17 . 1.381(3) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
O1S C1S . 1.230(5) ?
N1S C1S . 1.297(6) ?
N1S C4S . 1.399(7) ?
N1S C5S . 1.492(8) ?
C1S C2S . 1.483(9) ?
C2S C3S . 1.379(11) ?
C2S H2S1 . 0.9700 ?
C2S H2S2 . 0.9700 ?
C3S C4S . 1.659(11) ?
C3S H3S1 . 0.9700 ?
C3S H3S2 . 0.9700 ?
C4S H4S1 . 0.9700 ?
C4S H4S2 . 0.9700 ?
C5S H5S1 . 0.9600 ?
C5S H5S2 . 0.9600 ?
C5S H5S3 . 0.9600 ?
O1SA C1SA . 1.209(8) ?
N1SA C1SA . 1.293(9) ?
N1SA C4SA . 1.392(9) ?
N1SA C5SA . 1.492(11) ?
C1SA C2SA . 1.478(11) ?
C2SA C3SA . 1.361(14) ?
C2SA H2S3 . 0.9700 ?
C2SA H2S4 . 0.9700 ?
C3SA C4SA . 1.682(14) ?
C3SA H3S3 . 0.9700 ?
C3SA H3S4 . 0.9700 ?
C4SA H4S3 . 0.9700 ?
C4SA H4S4 . 0.9700 ?
C5SA H5S4 . 0.9600 ?
C5SA H5S5 . 0.9600 ?
C5SA H5S6 . 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
C1 N1 N2 C3 . . . . 0.4(2) ?
C1 N1 N2 C12 . . . . -177.00(19) ?
N2 N1 C1 C2 . . . . -0.2(3) ?
N2 N1 C1 C4 . . . . -179.1(2) ?
N1 C1 C2 C3 . . . . -0.1(3) ?
C4 C1 C2 C3 . . . . 178.7(3) ?
N1 N2 C3 C2 . . . . -0.5(2) ?
C12 N2 C3 C2 . . . . 176.5(2) ?
N1 N2 C3 C5 . . . . 176.31(19) ?
C12 N2 C3 C5 . . . . -6.7(3) ?
C1 C2 C3 N2 . . . . 0.4(3) ?
C1 C2 C3 C5 . . . . -176.2(2) ?
N1 C1 C4 F2 . . . . 74.9(11) ?
C2 C1 C4 F2 . . . . -103.9(11) ?
N1 C1 C4 F3 . . . . -48.7(7) ?
C2 C1 C4 F3 . . . . 132.5(6) ?
N1 C1 C4 F2A . . . . 133.1(5) ?
C2 C1 C4 F2A . . . . -45.7(7) ?
N1 C1 C4 F1A . . . . -105.2(9) ?
C2 C1 C4 F1A . . . . 76.1(10) ?
N1 C1 C4 F1 . . . . -162.2(10) ?
C2 C1 C4 F1 . . . . 19.0(11) ?
N1 C1 C4 F3A . . . . 15.1(9) ?
C2 C1 C4 F3A . . . . -163.6(9) ?
N2 C3 C5 C6 . . . . -34.0(3) ?
C2 C3 C5 C6 . . . . 142.0(2) ?
N2 C3 C5 C10 . . . . 149.0(2) ?
C2 C3 C5 C10 . . . . -35.0(3) ?
C10 C5 C6 C7 . . . . -0.5(3) ?
C3 C5 C6 C7 . . . . -177.62(19) ?
C5 C6 C7 C8 . . . . 0.5(3) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C6 C7 C8 C11 . . . . -179.7(3) ?
C7 C8 C9 C10 . . . . -0.8(4) ?
C11 C8 C9 C10 . . . . 179.1(3) ?
C8 C9 C10 C5 . . . . 0.7(4) ?
C6 C5 C10 C9 . . . . -0.1(3) ?
C3 C5 C10 C9 . . . . 177.2(2) ?
N1 N2 C12 C17 . . . . 124.9(2) ?
C3 N2 C12 C17 . . . . -52.0(3) ?
N1 N2 C12 C13 . . . . -52.1(3) ?
C3 N2 C12 C13 . . . . 131.1(2) ?
C17 C12 C13 C14 . . . . -0.5(4) ?
N2 C12 C13 C14 . . . . 176.4(2) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . 0.9(4) ?
C13 C14 C15 S1 . . . . -179.5(2) ?
O1 S1 C15 C16 . . . . -160.02(19) ?
O2 S1 C15 C16 . . . . -30.2(2) ?
N3 S1 C15 C16 . . . . 84.8(2) ?
O1 S1 C15 C14 . . . . 20.4(2) ?
O2 S1 C15 C14 . . . . 150.2(2) ?
N3 S1 C15 C14 . . . . -94.8(2) ?
C14 C15 C16 C17 . . . . -1.0(4) ?
S1 C15 C16 C17 . . . . 179.36(18) ?
C13 C12 C17 C16 . . . . 0.4(3) ?
N2 C12 C17 C16 . . . . -176.5(2) ?
C15 C16 C17 C12 . . . . 0.4(3) ?
C4S N1S C1S O1S . . . . 179.7(7) ?
C5S N1S C1S O1S . . . . -0.4(11) ?
C4S N1S C1S C2S . . . . 1.3(9) ?
C5S N1S C1S C2S . . . . -178.9(6) ?
O1S C1S C2S C3S . . . . 169.9(9) ?
N1S C1S C2S C3S . . . . -11.7(10) ?
C1S C2S C3S C4S . . . . 15.9(10) ?
C1S N1S C4S C3S . . . . 7.5(9) ?
C5S N1S C4S C3S . . . . -172.3(6) ?
C2S C3S C4S N1S . . . . -13.7(9) ?
C4SA N1SA C1SA O1SA . . . . -169.5(15) ?
C5SA N1SA C1SA O1SA . . . . 10(3) ?
C4SA N1SA C1SA C2SA . . . . 1(2) ?
C5SA N1SA C1SA C2SA . . . . -179.9(16) ?
O1SA C1SA C2SA C3SA . . . . 174(2) ?
N1SA C1SA C2SA C3SA . . . . 6(2) ?
C1SA C2SA C3SA C4SA . . . . -9(2) ?
C1SA N1SA C4SA C3SA . . . . -5(2) ?
C5SA N1SA C4SA C3SA . . . . 175.2(16) ?
C2SA C3SA C4SA N1SA . . . . 8(2) ?

_cod_database_fobs_code 2022173
