#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:31:38 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/42/1574201.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_1574201
loop_
_publ_author_name
'Zhou, Zhengzheng'
'Joshi, Vikram Chandrashekhar'
'Guo, Yiwang'
'Xiang, Tianyi'
'Wang, Zijian'
'Sun, Changquan Calvin'
_publ_section_title
;
 How elastically flexible can molecular crystals be? - a new record.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              5797
_journal_page_last               5802
_journal_paper_doi               10.1039/d5sc01260k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 F3 N3 O2 S'
_chemical_formula_sum            'C17 H14 F3 N3 O2 S'
_chemical_formula_weight         381.37
_chemical_name_common            'Celecoxib form I'
_chemical_name_systematic
4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-25 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                101.872(3)
_cell_angle_beta                 93.300(4)
_cell_angle_gamma                97.149(4)
_cell_formula_units_Z            6
_cell_length_a                   4.9533(10)
_cell_length_b                   16.174(3)
_cell_length_c                   32.778(6)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.53
_cell_volume                     2540.5(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'SHELXLE, Huschle, C. B. et al. J. Apps. Cryst. 44, (2011), 1281-1284.'
_computing_publication_material
'SHELXLE, Huschle, C. B. et al. J. Apps. Cryst. 44, (2011), 1281-1284.'
_computing_structure_refinement
'SHELXT, Sheldrick, G.M. Acta Cryst. (2015) A71, 3-8'
_computing_structure_solution
'SHELXT, Sheldrick, G.M. Acta Cryst. (2015) A71, 3-8'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            46595
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.912
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS, Krause, L. et al. J. Apple. Cryst. (2015), 48, 3-10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6452
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         9243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0315P)²+2.2328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7024
_reflns_number_total             9243
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc01260k3.cif
_cod_data_source_block           22169_c_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct' was changed
to 'direct' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1574201.cif.
;
_cod_original_cell_volume        2540.5(9)
_cod_database_code               1574201
_shelx_shelxl_version_number     2018/3
_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, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.41710(12) -0.03907(4) 0.56278(2) 0.02235(15) Uani 1 1 d . . . . .
F1A F -0.0645(4) 0.46768(12) 0.68636(5) 0.0562(5) Uani 1 1 d . . . . .
F2A F 0.3125(4) 0.54827(12) 0.68860(6) 0.0645(6) Uani 1 1 d . . . . .
F3A F -0.0330(5) 0.56385(12) 0.65003(6) 0.0706(7) Uani 1 1 d . . . . .
O1A O 0.3011(4) -0.07803(11) 0.52141(5) 0.0294(4) Uani 1 1 d . . . . .
O2A O 0.6961(3) -0.04376(11) 0.57465(6) 0.0291(4) Uani 1 1 d . . . . .
N1A N 0.2365(5) -0.08132(14) 0.59446(7) 0.0248(5) Uani 1 1 d . . . . .
N2A N 0.2911(4) 0.32999(13) 0.59252(6) 0.0245(5) Uani 1 1 d . . . . .
N3A N 0.2245(5) 0.36753(13) 0.63090(6) 0.0282(5) Uani 1 1 d . . . . .
C1A C 0.3834(5) 0.07113(15) 0.57150(7) 0.0205(5) Uani 1 1 d . . . . .
C2A C 0.5594(5) 0.12970(16) 0.60122(8) 0.0252(6) Uani 1 1 d . . . . .
H2A H 0.699458 0.111149 0.616694 0.030 Uiso 1 1 calc R U . . .
C3A C 0.5298(5) 0.21538(16) 0.60822(8) 0.0258(6) Uani 1 1 d . . . . .
H3A H 0.648681 0.256105 0.628556 0.031 Uiso 1 1 calc R U . . .
C4A C 0.3246(5) 0.24090(15) 0.58519(7) 0.0230(5) Uani 1 1 d . . . . .
C5A C 0.1490(5) 0.18307(16) 0.55545(8) 0.0265(6) Uani 1 1 d . . . . .
H5A H 0.009901 0.201850 0.539883 0.032 Uiso 1 1 calc R U . . .
C6A C 0.1781(5) 0.09701(16) 0.54856(8) 0.0268(6) Uani 1 1 d . . . . .
H6A H 0.058385 0.056331 0.528316 0.032 Uiso 1 1 calc R U . . .
C7A C 0.1789(6) 0.44473(17) 0.62649(8) 0.0332(7) Uani 1 1 d . . . . .
C8A C 0.2168(6) 0.45763(17) 0.58672(9) 0.0377(7) Uani 1 1 d . . . . .
H8A H 0.196615 0.507688 0.576597 0.045 Uiso 1 1 calc R U . . .
C9A C 0.2900(6) 0.38264(16) 0.56481(8) 0.0293(6) Uani 1 1 d . . . . .
C10A C 0.0996(7) 0.50572(18) 0.66283(9) 0.0416(8) Uani 1 1 d . . . . .
C11A C 0.3522(5) 0.36031(16) 0.52094(8) 0.0273(6) Uani 1 1 d . . . . .
C12A C 0.2319(9) 0.3969(3) 0.49193(10) 0.0692(13) Uani 1 1 d . . . . .
H12A H 0.111960 0.437403 0.500614 0.083 Uiso 1 1 calc R U . . .
C13A C 0.2808(8) 0.3764(3) 0.45019(11) 0.0739(13) Uani 1 1 d . . . . .
H13A H 0.194111 0.403337 0.430915 0.089 Uiso 1 1 calc R U . . .
C14A C 0.4493(7) 0.31864(19) 0.43601(9) 0.0427(8) Uani 1 1 d . . . . .
C15A C 0.5742(8) 0.2838(2) 0.46518(11) 0.0604(11) Uani 1 1 d . . . . .
H15A H 0.696495 0.244054 0.456426 0.072 Uiso 1 1 calc R U . . .
C16A C 0.5295(7) 0.3040(2) 0.50688(10) 0.0492(9) Uani 1 1 d . . . . .
H16A H 0.622687 0.278705 0.526218 0.059 Uiso 1 1 calc R U . . .
C17A C 0.4911(9) 0.2929(3) 0.39013(10) 0.0711(12) Uani 1 1 d . . . . .
H17A H 0.384627 0.237015 0.378275 0.107 Uiso 1 1 calc R U . . .
H17B H 0.685228 0.289774 0.386841 0.107 Uiso 1 1 calc R U . . .
H17C H 0.430709 0.335326 0.375474 0.107 Uiso 1 1 calc R U . . .
H1AA H 0.302(6) -0.0616(19) 0.6194(10) 0.040(9) Uiso 1 1 d . . . . .
H1AB H 0.059(7) -0.076(2) 0.5897(10) 0.055(10) Uiso 1 1 d . . . . .
S1B S 0.78165(12) 0.00930(4) 0.69309(2) 0.02168(14) Uani 1 1 d . . . . .
F1B F -0.0312(3) -0.07261(11) 0.92340(6) 0.0483(5) Uani 1 1 d . . . . .
F2B F 0.3098(4) -0.13636(11) 0.93286(6) 0.0540(5) Uani 1 1 d . . . . .
F3B F 0.2274(4) -0.03193(12) 0.98012(5) 0.0548(5) Uani 1 1 d . . . . .
O1B O 0.5196(3) 0.02269(11) 0.67619(5) 0.0276(4) Uani 1 1 d . . . . .
O2B O 0.8772(4) -0.07072(10) 0.67925(5) 0.0288(4) Uani 1 1 d . . . . .
N1B N 1.0008(5) 0.08204(14) 0.68250(7) 0.0241(5) Uani 1 1 d . . . . .
N2B N 0.6075(4) 0.04902(13) 0.87314(6) 0.0257(5) Uani 1 1 d . . . . .
N3B N 0.4584(4) -0.02229(13) 0.88072(7) 0.0285(5) Uani 1 1 d . . . . .
C1B C 0.7604(5) 0.02673(15) 0.74779(7) 0.0220(5) Uani 1 1 d . . . . .
C2B C 0.6181(5) 0.09134(16) 0.76688(8) 0.0253(6) Uani 1 1 d . . . . .
H2B H 0.551314 0.128876 0.751162 0.030 Uiso 1 1 calc R U . . .
C3B C 0.5749(5) 0.10051(16) 0.80858(8) 0.0269(6) Uani 1 1 d . . . . .
H3B H 0.477524 0.144168 0.821823 0.032 Uiso 1 1 calc R U . . .
C4B C 0.6750(5) 0.04536(16) 0.83105(8) 0.0254(6) Uani 1 1 d . . . . .
C5B C 0.8264(5) -0.01683(16) 0.81279(8) 0.0281(6) Uani 1 1 d . . . . .
H5B H 0.900788 -0.052359 0.828957 0.034 Uiso 1 1 calc R U . . .
C6B C 0.8681(5) -0.02660(16) 0.77075(8) 0.0266(6) Uani 1 1 d . . . . .
H6B H 0.969347 -0.069387 0.757729 0.032 Uiso 1 1 calc R U . . .
C7B C 0.4012(5) 0.00186(16) 0.92020(8) 0.0262(6) Uani 1 1 d . . . . .
C8B C 0.5078(5) 0.08611(16) 0.93796(8) 0.0294(6) Uani 1 1 d . . . . .
H8B H 0.491835 0.116575 0.965566 0.035 Uiso 1 1 calc R U . . .
C9B C 0.6415(5) 0.11606(16) 0.90708(8) 0.0266(6) Uani 1 1 d . . . . .
C10B C 0.2293(6) -0.05935(17) 0.93919(8) 0.0302(6) Uani 1 1 d . . . . .
C11B C 0.7948(5) 0.20050(16) 0.90923(8) 0.0261(6) Uani 1 1 d . . . . .
C12B C 0.7271(6) 0.26912(17) 0.93819(8) 0.0335(7) Uani 1 1 d . . . . .
H12B H 0.579665 0.260171 0.954797 0.040 Uiso 1 1 calc R U . . .
C13B C 0.8709(6) 0.35016(18) 0.94318(9) 0.0375(7) Uani 1 1 d . . . . .
H13B H 0.822524 0.395682 0.963461 0.045 Uiso 1 1 calc R U . . .
C14B C 1.0835(6) 0.36578(17) 0.91912(9) 0.0328(6) Uani 1 1 d . . . . .
C15B C 1.1489(6) 0.29787(19) 0.88990(9) 0.0381(7) Uani 1 1 d . . . . .
H15B H 1.292165 0.307548 0.872667 0.046 Uiso 1 1 calc R U . . .
C16B C 1.0106(5) 0.21645(18) 0.88526(9) 0.0326(6) Uani 1 1 d . . . . .
H16B H 1.063285 0.170858 0.865492 0.039 Uiso 1 1 calc R U . . .
C17B C 1.2386(7) 0.45468(19) 0.92571(11) 0.0484(8) Uani 1 1 d . . . . .
H17D H 1.352376 0.458196 0.902462 0.073 Uiso 1 1 calc R U . . .
H17E H 1.355101 0.467442 0.952046 0.073 Uiso 1 1 calc R U . . .
H17F H 1.109118 0.496074 0.926885 0.073 Uiso 1 1 calc R U . . .
H1BB H 1.174(8) 0.073(2) 0.6859(11) 0.073 Uiso 1 1 d . U . . .
H1BA H 0.970(8) 0.132(2) 0.6921(11) 0.073 Uiso 1 1 d . U . . .
S1C S 1.15541(13) 0.29873(4) 0.74432(2) 0.02283(15) Uani 1 1 d . . . . .
F1C F 0.6436(4) 0.62543(10) 0.97658(5) 0.0430(4) Uani 1 1 d . . . . .
F2C F 0.3127(3) 0.67981(12) 0.95279(5) 0.0472(5) Uani 1 1 d . . . . .
F3C F 0.6891(4) 0.75946(10) 0.97713(5) 0.0485(5) Uani 1 1 d . . . . .
O1C O 0.9039(3) 0.26296(11) 0.71850(5) 0.0280(4) Uani 1 1 d . . . . .
O2C O 1.2724(4) 0.24588(11) 0.76859(5) 0.0290(4) Uani 1 1 d . . . . .
N1C N 1.3758(5) 0.33050(15) 0.71537(7) 0.0269(5) Uani 1 1 d . . . . .
N2C N 0.8406(4) 0.60086(12) 0.85800(6) 0.0234(5) Uani 1 1 d . . . . .
N3C N 0.7488(4) 0.59070(13) 0.89528(6) 0.0266(5) Uani 1 1 d . . . . .
C1C C 1.0816(5) 0.39034(15) 0.77890(7) 0.0211(5) Uani 1 1 d . . . . .
C2C C 0.8756(5) 0.37813(16) 0.80517(7) 0.0247(6) Uani 1 1 d . . . . .
H2C H 0.788480 0.322317 0.805034 0.030 Uiso 1 1 calc R U . . .
C3C C 0.7998(5) 0.44822(15) 0.83142(8) 0.0252(6) Uani 1 1 d . . . . .
H3C H 0.657864 0.440814 0.849181 0.030 Uiso 1 1 calc R U . . .
C4C C 0.9308(5) 0.52949(15) 0.83185(7) 0.0226(5) Uani 1 1 d . . . . .
C5C C 1.1449(5) 0.54087(16) 0.80724(8) 0.0256(6) Uani 1 1 d . . . . .
H5C H 1.240847 0.596251 0.808863 0.031 Uiso 1 1 calc R U . . .
C6C C 1.2183(5) 0.47092(15) 0.78023(8) 0.0248(6) Uani 1 1 d . . . . .
H6C H 1.361830 0.478325 0.762729 0.030 Uiso 1 1 calc R U . . .
C7C C 0.6874(5) 0.66700(16) 0.91246(8) 0.0257(6) Uani 1 1 d . . . . .
C8C C 0.7348(5) 0.72614(16) 0.88702(8) 0.0271(6) Uani 1 1 d . . . . .
H8C H 0.704934 0.784138 0.892815 0.033 Uiso 1 1 calc R U . . .
C9C C 0.8335(5) 0.68243(15) 0.85200(8) 0.0249(6) Uani 1 1 d . . . . .
C10C C 0.5835(6) 0.68213(17) 0.95454(8) 0.0312(6) Uani 1 1 d . . . . .
C11C C 0.9249(5) 0.71213(15) 0.81468(8) 0.0246(6) Uani 1 1 d . . . . .
C12C C 1.1430(5) 0.77722(16) 0.81944(8) 0.0282(6) Uani 1 1 d . . . . .
H12C H 1.223298 0.804595 0.846652 0.034 Uiso 1 1 calc R U . . .
C13C C 1.2435(6) 0.80232(17) 0.78478(9) 0.0329(6) Uani 1 1 d . . . . .
H13C H 1.393797 0.846606 0.788539 0.040 Uiso 1 1 calc R U . . .
C14C C 1.1298(6) 0.76423(16) 0.74453(8) 0.0302(6) Uani 1 1 d . . . . .
C15C C 0.9053(6) 0.70142(17) 0.74022(8) 0.0308(6) Uani 1 1 d . . . . .
H15C H 0.819715 0.676001 0.713091 0.037 Uiso 1 1 calc R U . . .
C16C C 0.8041(5) 0.67517(16) 0.77454(8) 0.0292(6) Uani 1 1 d . . . . .
H16C H 0.651362 0.631720 0.770789 0.035 Uiso 1 1 calc R U . . .
C17C C 1.2517(7) 0.78927(19) 0.70700(9) 0.0421(8) Uani 1 1 d . . . . .
H17G H 1.401885 0.756560 0.699395 0.063 Uiso 1 1 calc R U . . .
H17H H 1.321287 0.850355 0.713765 0.063 Uiso 1 1 calc R U . . .
H17I H 1.111262 0.777175 0.683453 0.063 Uiso 1 1 calc R U . . .
H1CA H 1.315(7) 0.337(2) 0.6882(11) 0.063 Uiso 1 1 d . U . . .
H1CB H 1.525(6) 0.3174(18) 0.7179(9) 0.031(8) 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A S1A O2A 120.03(11) . . ?
O1A S1A N1A 107.07(12) . . ?
O2A S1A N1A 106.75(12) . . ?
O1A S1A C1A 107.69(11) . . ?
O2A S1A C1A 106.47(11) . . ?
N1A S1A C1A 108.41(11) . . ?
S1A N1A H1AA 110(2) . . ?
S1A N1A H1AB 110(2) . . ?
H1AA N1A H1AB 114(3) . . ?
N3A N2A C9A 112.6(2) . . ?
N3A N2A C4A 117.91(19) . . ?
C9A N2A C4A 129.2(2) . . ?
C7A N3A N2A 103.7(2) . . ?
C6A C1A C2A 121.0(2) . . ?
C6A C1A S1A 119.04(19) . . ?
C2A C1A S1A 119.94(19) . . ?
C3A C2A C1A 119.6(2) . . ?
C3A C2A H2A 120.2 . . ?
C1A C2A H2A 120.2 . . ?
C4A C3A C2A 119.1(2) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C5A C4A C3A 121.6(2) . . ?
C5A C4A N2A 118.9(2) . . ?
C3A C4A N2A 119.5(2) . . ?
C4A C5A C6A 119.2(2) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
C1A C6A C5A 119.4(2) . . ?
C1A C6A H6A 120.3 . . ?
C5A C6A H6A 120.3 . . ?
N3A C7A C8A 112.7(2) . . ?
N3A C7A C10A 119.4(2) . . ?
C8A C7A C10A 127.9(3) . . ?
C9A C8A C7A 105.6(2) . . ?
C9A C8A H8A 127.2 . . ?
C7A C8A H8A 127.2 . . ?
N2A C9A C8A 105.5(2) . . ?
N2A C9A C11A 125.4(2) . . ?
C8A C9A C11A 129.1(2) . . ?
F3A C10A F1A 106.9(3) . . ?
F3A C10A F2A 106.8(3) . . ?
F1A C10A F2A 105.9(2) . . ?
F3A C10A C7A 110.8(2) . . ?
F1A C10A C7A 112.8(2) . . ?
F2A C10A C7A 113.2(3) . . ?
C12A C11A C16A 116.8(3) . . ?
C12A C11A C9A 119.7(2) . . ?
C16A C11A C9A 123.5(2) . . ?
C11A C12A C13A 121.5(3) . . ?
C11A C12A H12A 119.3 . . ?
C13A C12A H12A 119.3 . . ?
C14A C13A C12A 121.8(3) . . ?
C14A C13A H13A 119.1 . . ?
C12A C13A H13A 119.1 . . ?
C13A C14A C15A 116.6(3) . . ?
C13A C14A C17A 121.7(3) . . ?
C15A C14A C17A 121.7(3) . . ?
C14A C15A C16A 122.3(3) . . ?
C14A C15A H15A 118.8 . . ?
C16A C15A H15A 118.8 . . ?
C11A C16A C15A 120.9(3) . . ?
C11A C16A H16A 119.5 . . ?
C15A C16A H16A 119.5 . . ?
C14A C17A H17A 109.5 . . ?
C14A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C14A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O2B S1B O1B 119.43(11) . . ?
O2B S1B N1B 107.52(12) . . ?
O1B S1B N1B 106.15(12) . . ?
O2B S1B C1B 108.69(11) . . ?
O1B S1B C1B 105.12(11) . . ?
N1B S1B C1B 109.68(11) . . ?
S1B N1B H1BB 114(2) . . ?
S1B N1B H1BA 114(3) . . ?
H1BB N1B H1BA 116(3) . . ?
N3B N2B C9B 112.7(2) . . ?
N3B N2B C4B 116.37(19) . . ?
C9B N2B C4B 130.5(2) . . ?
C7B N3B N2B 103.4(2) . . ?
C6B C1B C2B 120.8(2) . . ?
C6B C1B S1B 120.42(19) . . ?
C2B C1B S1B 118.69(19) . . ?
C3B C2B C1B 119.7(2) . . ?
C3B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
C2B C3B C4B 119.3(2) . . ?
C2B C3B H3B 120.3 . . ?
C4B C3B H3B 120.3 . . ?
C3B C4B C5B 121.4(2) . . ?
C3B C4B N2B 119.5(2) . . ?
C5B C4B N2B 119.0(2) . . ?
C6B C5B C4B 119.3(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C1B 119.4(2) . . ?
C5B C6B H6B 120.3 . . ?
C1B C6B H6B 120.3 . . ?
N3B C7B C8B 112.9(2) . . ?
N3B C7B C10B 118.9(2) . . ?
C8B C7B C10B 128.2(2) . . ?
C9B C8B C7B 105.5(2) . . ?
C9B C8B H8B 127.3 . . ?
C7B C8B H8B 127.3 . . ?
N2B C9B C8B 105.6(2) . . ?
N2B C9B C11B 126.0(2) . . ?
C8B C9B C11B 128.5(2) . . ?
F3B C10B F2B 107.3(2) . . ?
F3B C10B F1B 106.4(2) . . ?
F2B C10B F1B 105.4(2) . . ?
F3B C10B C7B 111.9(2) . . ?
F2B C10B C7B 113.1(2) . . ?
F1B C10B C7B 112.2(2) . . ?
C16B C11B C12B 117.6(2) . . ?
C16B C11B C9B 124.3(2) . . ?
C12B C11B C9B 118.0(2) . . ?
C13B C12B C11B 121.2(3) . . ?
C13B C12B H12B 119.4 . . ?
C11B C12B H12B 119.4 . . ?
C14B C13B C12B 121.0(3) . . ?
C14B C13B H13B 119.5 . . ?
C12B C13B H13B 119.5 . . ?
C13B C14B C15B 118.0(3) . . ?
C13B C14B C17B 119.7(3) . . ?
C15B C14B C17B 122.3(3) . . ?
C16B C15B C14B 121.5(3) . . ?
C16B C15B H15B 119.2 . . ?
C14B C15B H15B 119.2 . . ?
C15B C16B C11B 120.7(3) . . ?
C15B C16B H16B 119.7 . . ?
C11B C16B H16B 119.7 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O2C S1C O1C 117.58(11) . . ?
O2C S1C N1C 109.24(13) . . ?
O1C S1C N1C 108.56(12) . . ?
O2C S1C C1C 108.17(11) . . ?
O1C S1C C1C 105.94(11) . . ?
N1C S1C C1C 106.83(12) . . ?
S1C N1C H1CA 119(2) . . ?
S1C N1C H1CB 117(2) . . ?
H1CA N1C H1CB 116(3) . . ?
N3C N2C C9C 112.18(19) . . ?
N3C N2C C4C 117.9(2) . . ?
C9C N2C C4C 129.9(2) . . ?
C7C N3C N2C 103.8(2) . . ?
C6C C1C C2C 120.9(2) . . ?
C6C C1C S1C 122.44(19) . . ?
C2C C1C S1C 116.71(18) . . ?
C3C C2C C1C 119.2(2) . . ?
C3C C2C H2C 120.4 . . ?
C1C C2C H2C 120.4 . . ?
C2C C3C C4C 120.1(2) . . ?
C2C C3C H3C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
C5C C4C C3C 120.5(2) . . ?
C5C C4C N2C 120.7(2) . . ?
C3C C4C N2C 118.8(2) . . ?
C4C C5C C6C 119.6(2) . . ?
C4C C5C H5C 120.2 . . ?
C6C C5C H5C 120.2 . . ?
C1C C6C C5C 119.7(2) . . ?
C1C C6C H6C 120.2 . . ?
C5C C6C H6C 120.2 . . ?
N3C C7C C8C 112.7(2) . . ?
N3C C7C C10C 120.1(2) . . ?
C8C C7C C10C 127.2(2) . . ?
C9C C8C C7C 105.2(2) . . ?
C9C C8C H8C 127.4 . . ?
C7C C8C H8C 127.4 . . ?
C8C C9C N2C 106.1(2) . . ?
C8C C9C C11C 129.9(2) . . ?
N2C C9C C11C 124.1(2) . . ?
F1C C10C F2C 106.6(2) . . ?
F1C C10C F3C 107.1(2) . . ?
F2C C10C F3C 106.2(2) . . ?
F1C C10C C7C 113.1(2) . . ?
F2C C10C C7C 112.5(2) . . ?
F3C C10C C7C 110.9(2) . . ?
C12C C11C C16C 118.7(2) . . ?
C12C C11C C9C 119.2(2) . . ?
C16C C11C C9C 122.0(2) . . ?
C13C C12C C11C 120.3(2) . . ?
C13C C12C H12C 119.9 . . ?
C11C C12C H12C 119.9 . . ?
C12C C13C C14C 121.5(3) . . ?
C12C C13C H13C 119.3 . . ?
C14C C13C H13C 119.3 . . ?
C15C C14C C13C 117.8(2) . . ?
C15C C14C C17C 121.6(3) . . ?
C13C C14C C17C 120.6(3) . . ?
C16C C15C C14C 121.4(3) . . ?
C16C C15C H15C 119.3 . . ?
C14C C15C H15C 119.3 . . ?
C15C C16C C11C 120.3(3) . . ?
C15C C16C H16C 119.9 . . ?
C11C C16C H16C 119.9 . . ?
C14C C17C H17G 109.5 . . ?
C14C C17C H17H 109.5 . . ?
H17G C17C H17H 109.5 . . ?
C14C C17C H17I 109.5 . . ?
H17G C17C H17I 109.5 . . ?
H17H C17C H17I 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O1A 1.4265(18) . ?
S1A O2A 1.4296(18) . ?
S1A N1A 1.610(2) . ?
S1A C1A 1.777(2) . ?
F1A C10A 1.333(4) . ?
F2A C10A 1.333(4) . ?
F3A C10A 1.332(3) . ?
N1A H1AA 0.84(3) . ?
N1A H1AB 0.90(4) . ?
N2A N3A 1.358(3) . ?
N2A C9A 1.367(3) . ?
N2A C4A 1.443(3) . ?
N3A C7A 1.331(3) . ?
C1A C6A 1.387(3) . ?
C1A C2A 1.387(3) . ?
C2A C3A 1.385(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.385(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.381(3) . ?
C5A C6A 1.390(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.381(4) . ?
C7A C10A 1.488(4) . ?
C8A C9A 1.378(4) . ?
C8A H8A 0.9500 . ?
C9A C11A 1.469(4) . ?
C11A C12A 1.365(4) . ?
C11A C16A 1.373(4) . ?
C12A C13A 1.383(4) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.358(5) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.362(5) . ?
C14A C17A 1.509(4) . ?
C15A C16A 1.376(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
S1B O2B 1.4285(17) . ?
S1B O1B 1.4404(18) . ?
S1B N1B 1.605(2) . ?
S1B C1B 1.768(2) . ?
F1B C10B 1.337(3) . ?
F2B C10B 1.334(3) . ?
F3B C10B 1.325(3) . ?
N1B H1BB 0.89(4) . ?
N1B H1BA 0.85(4) . ?
N2B N3B 1.365(3) . ?
N2B C9B 1.371(3) . ?
N2B C4B 1.429(3) . ?
N3B C7B 1.330(3) . ?
C1B C6B 1.389(3) . ?
C1B C2B 1.395(3) . ?
C2B C3B 1.376(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.387(4) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(4) . ?
C5B C6B 1.385(4) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.391(4) . ?
C7B C10B 1.482(4) . ?
C8B C9B 1.377(4) . ?
C8B H8B 0.9500 . ?
C9B C11B 1.464(4) . ?
C11B C16B 1.392(4) . ?
C11B C12B 1.393(4) . ?
C12B C13B 1.385(4) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.380(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.386(4) . ?
C14B C17B 1.511(4) . ?
C15B C16B 1.381(4) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
S1C O2C 1.4316(18) . ?
S1C O1C 1.4495(18) . ?
S1C N1C 1.593(2) . ?
S1C C1C 1.762(2) . ?
F1C C10C 1.329(3) . ?
F2C C10C 1.335(3) . ?
F3C C10C 1.341(3) . ?
N1C H1CA 0.96(4) . ?
N1C H1CB 0.80(3) . ?
N2C N3C 1.362(3) . ?
N2C C9C 1.378(3) . ?
N2C C4C 1.426(3) . ?
N3C C7C 1.327(3) . ?
C1C C6C 1.383(3) . ?
C1C C2C 1.394(3) . ?
C2C C3C 1.381(3) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.389(3) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.386(3) . ?
C5C C6C 1.387(3) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
C7C C8C 1.400(4) . ?
C7C C10C 1.484(4) . ?
C8C C9C 1.368(3) . ?
C8C H8C 0.9500 . ?
C9C C11C 1.478(4) . ?
C11C C12C 1.389(4) . ?
C11C C16C 1.394(4) . ?
C12C C13C 1.382(4) . ?
C12C H12C 0.9500 . ?
C13C C14C 1.390(4) . ?
C13C H13C 0.9500 . ?
C14C C15C 1.389(4) . ?
C14C C17C 1.507(4) . ?
C15C C16C 1.381(4) . ?
C15C H15C 0.9500 . ?
C16C H16C 0.9500 . ?
C17C H17G 0.9800 . ?
C17C H17H 0.9800 . ?
C17C H17I 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1AA O1B 0.84(3) 2.20(3) 3.017(3) 163(3) . yes
N1B H1BA O1C 0.85(4) 2.18(4) 3.030(3) 178(4) . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N2A N3A C7A 0.6(3) . . . . ?
C4A N2A N3A C7A -173.3(2) . . . . ?
O1A S1A C1A C6A 24.7(2) . . . . ?
O2A S1A C1A C6A 154.6(2) . . . . ?
N1A S1A C1A C6A -90.9(2) . . . . ?
O1A S1A C1A C2A -156.0(2) . . . . ?
O2A S1A C1A C2A -26.1(2) . . . . ?
N1A S1A C1A C2A 88.5(2) . . . . ?
C6A C1A C2A C3A 0.1(4) . . . . ?
S1A C1A C2A C3A -179.20(19) . . . . ?
C1A C2A C3A C4A -0.2(4) . . . . ?
C2A C3A C4A C5A 0.0(4) . . . . ?
C2A C3A C4A N2A 179.5(2) . . . . ?
N3A N2A C4A C5A 116.5(3) . . . . ?
C9A N2A C4A C5A -56.3(4) . . . . ?
N3A N2A C4A C3A -63.0(3) . . . . ?
C9A N2A C4A C3A 124.2(3) . . . . ?
C3A C4A C5A C6A 0.3(4) . . . . ?
N2A C4A C5A C6A -179.3(2) . . . . ?
C2A C1A C6A C5A 0.1(4) . . . . ?
S1A C1A C6A C5A 179.47(19) . . . . ?
C4A C5A C6A C1A -0.3(4) . . . . ?
N2A N3A C7A C8A -0.6(3) . . . . ?
N2A N3A C7A C10A -179.9(3) . . . . ?
N3A C7A C8A C9A 0.3(4) . . . . ?
C10A C7A C8A C9A 179.6(3) . . . . ?
N3A N2A C9A C8A -0.4(3) . . . . ?
C4A N2A C9A C8A 172.7(3) . . . . ?
N3A N2A C9A C11A -179.7(2) . . . . ?
C4A N2A C9A C11A -6.6(4) . . . . ?
C7A C8A C9A N2A 0.1(3) . . . . ?
C7A C8A C9A C11A 179.3(3) . . . . ?
N3A C7A C10A F3A -156.8(3) . . . . ?
C8A C7A C10A F3A 24.0(5) . . . . ?
N3A C7A C10A F1A -37.0(4) . . . . ?
C8A C7A C10A F1A 143.7(3) . . . . ?
N3A C7A C10A F2A 83.3(3) . . . . ?
C8A C7A C10A F2A -96.0(4) . . . . ?
N2A C9A C11A C12A 150.0(3) . . . . ?
C8A C9A C11A C12A -29.1(5) . . . . ?
N2A C9A C11A C16A -30.5(5) . . . . ?
C8A C9A C11A C16A 150.4(3) . . . . ?
C16A C11A C12A C13A 1.8(6) . . . . ?
C9A C11A C12A C13A -178.7(4) . . . . ?
C11A C12A C13A C14A 0.3(7) . . . . ?
C12A C13A C14A C15A -1.8(6) . . . . ?
C12A C13A C14A C17A 176.8(4) . . . . ?
C13A C14A C15A C16A 1.3(6) . . . . ?
C17A C14A C15A C16A -177.3(4) . . . . ?
C12A C11A C16A C15A -2.3(5) . . . . ?
C9A C11A C16A C15A 178.2(3) . . . . ?
C14A C15A C16A C11A 0.8(6) . . . . ?
C9B N2B N3B C7B -0.2(3) . . . . ?
C4B N2B N3B C7B -173.5(2) . . . . ?
O2B S1B C1B C6B 9.3(2) . . . . ?
O1B S1B C1B C6B 138.3(2) . . . . ?
N1B S1B C1B C6B -108.0(2) . . . . ?
O2B S1B C1B C2B -166.50(19) . . . . ?
O1B S1B C1B C2B -37.5(2) . . . . ?
N1B S1B C1B C2B 76.2(2) . . . . ?
C6B C1B C2B C3B -2.4(4) . . . . ?
S1B C1B C2B C3B 173.4(2) . . . . ?
C1B C2B C3B C4B 0.3(4) . . . . ?
C2B C3B C4B C5B 2.4(4) . . . . ?
C2B C3B C4B N2B -173.8(2) . . . . ?
N3B N2B C4B C3B 116.8(3) . . . . ?
C9B N2B C4B C3B -55.1(4) . . . . ?
N3B N2B C4B C5B -59.5(3) . . . . ?
C9B N2B C4B C5B 128.7(3) . . . . ?
C3B C4B C5B C6B -3.0(4) . . . . ?
N2B C4B C5B C6B 173.2(2) . . . . ?
C4B C5B C6B C1B 0.8(4) . . . . ?
C2B C1B C6B C5B 1.9(4) . . . . ?
S1B C1B C6B C5B -173.9(2) . . . . ?
N2B N3B C7B C8B 0.2(3) . . . . ?
N2B N3B C7B C10B 177.7(2) . . . . ?
N3B C7B C8B C9B -0.2(3) . . . . ?
C10B C7B C8B C9B -177.4(3) . . . . ?
N3B N2B C9B C8B 0.1(3) . . . . ?
C4B N2B C9B C8B 172.2(3) . . . . ?
N3B N2B C9B C11B 178.8(2) . . . . ?
C4B N2B C9B C11B -9.0(4) . . . . ?
C7B C8B C9B N2B 0.0(3) . . . . ?
C7B C8B C9B C11B -178.7(3) . . . . ?
N3B C7B C10B F3B 169.5(2) . . . . ?
C8B C7B C10B F3B -13.4(4) . . . . ?
N3B C7B C10B F2B 48.2(3) . . . . ?
C8B C7B C10B F2B -134.7(3) . . . . ?
N3B C7B C10B F1B -70.9(3) . . . . ?
C8B C7B C10B F1B 106.2(3) . . . . ?
N2B C9B C11B C16B -26.5(4) . . . . ?
C8B C9B C11B C16B 152.0(3) . . . . ?
N2B C9B C11B C12B 155.8(3) . . . . ?
C8B C9B C11B C12B -25.7(4) . . . . ?
C16B C11B C12B C13B -0.5(4) . . . . ?
C9B C11B C12B C13B 177.3(3) . . . . ?
C11B C12B C13B C14B 1.0(4) . . . . ?
C12B C13B C14B C15B -0.1(4) . . . . ?
C12B C13B C14B C17B -179.2(3) . . . . ?
C13B C14B C15B C16B -1.2(4) . . . . ?
C17B C14B C15B C16B 177.8(3) . . . . ?
C14B C15B C16B C11B 1.7(4) . . . . ?
C12B C11B C16B C15B -0.8(4) . . . . ?
C9B C11B C16B C15B -178.5(3) . . . . ?
C9C N2C N3C C7C -0.6(3) . . . . ?
C4C N2C N3C C7C 178.5(2) . . . . ?
O2C S1C C1C C6C 112.8(2) . . . . ?
O1C S1C C1C C6C -120.3(2) . . . . ?
N1C S1C C1C C6C -4.7(3) . . . . ?
O2C S1C C1C C2C -67.4(2) . . . . ?
O1C S1C C1C C2C 59.5(2) . . . . ?
N1C S1C C1C C2C 175.1(2) . . . . ?
C6C C1C C2C C3C 3.0(4) . . . . ?
S1C C1C C2C C3C -176.8(2) . . . . ?
C1C C2C C3C C4C -0.9(4) . . . . ?
C2C C3C C4C C5C -2.4(4) . . . . ?
C2C C3C C4C N2C 177.5(2) . . . . ?
N3C N2C C4C C5C -145.7(2) . . . . ?
C9C N2C C4C C5C 33.3(4) . . . . ?
N3C N2C C4C C3C 34.5(3) . . . . ?
C9C N2C C4C C3C -146.6(3) . . . . ?
C3C C4C C5C C6C 3.7(4) . . . . ?
N2C C4C C5C C6C -176.2(2) . . . . ?
C2C C1C C6C C5C -1.7(4) . . . . ?
S1C C1C C6C C5C 178.0(2) . . . . ?
C4C C5C C6C C1C -1.6(4) . . . . ?
N2C N3C C7C C8C 0.6(3) . . . . ?
N2C N3C C7C C10C -178.8(2) . . . . ?
N3C C7C C8C C9C -0.3(3) . . . . ?
C10C C7C C8C C9C 179.0(3) . . . . ?
C7C C8C C9C N2C 0.0(3) . . . . ?
C7C C8C C9C C11C -178.5(3) . . . . ?
N3C N2C C9C C8C 0.4(3) . . . . ?
C4C N2C C9C C8C -178.6(2) . . . . ?
N3C N2C C9C C11C 179.0(2) . . . . ?
C4C N2C C9C C11C 0.0(4) . . . . ?
N3C C7C C10C F1C 20.4(4) . . . . ?
C8C C7C C10C F1C -158.9(3) . . . . ?
N3C C7C C10C F2C -100.4(3) . . . . ?
C8C C7C C10C F2C 80.3(3) . . . . ?
N3C C7C C10C F3C 140.7(3) . . . . ?
C8C C7C C10C F3C -38.6(4) . . . . ?
C8C C9C C11C C12C 60.8(4) . . . . ?
N2C C9C C11C C12C -117.4(3) . . . . ?
C8C C9C C11C C16C -121.1(3) . . . . ?
N2C C9C C11C C16C 60.7(4) . . . . ?
C16C C11C C12C C13C -2.4(4) . . . . ?
C9C C11C C12C C13C 175.8(2) . . . . ?
C11C C12C C13C C14C 0.5(4) . . . . ?
C12C C13C C14C C15C 1.8(4) . . . . ?
C12C C13C C14C C17C -176.7(2) . . . . ?
C13C C14C C15C C16C -2.4(4) . . . . ?
C17C C14C C15C C16C 176.2(2) . . . . ?
C14C C15C C16C C11C 0.6(4) . . . . ?
C12C C11C C16C C15C 1.8(4) . . . . ?
C9C C11C C16C C15C -176.3(2) . . . . ?
