#------------------------------------------------------------------------------
#$Date: 2020-10-21 07:06:39 +0300 (Wed, 21 Oct 2020) $
#$Revision: 258507 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241423.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_7241423
loop_
_publ_author_name
'Laube, Markus'
'Gassner, Cemena'
'Neuber, Christin'
'Wodtke, Robert'
'Ullrich, Martin'
'Haase-Kohn, Cathleen'
'Löser, Reik'
'Köckerling, Martin'
'Kopka, Klaus'
'Kniess, Torsten'
'Hey-Hawkins, Evamarie'
'Pietzsch, Jens'
_publ_section_title
;
 Deuteration versus ethylation -- strategies to improve the metabolic fate
 of an 18F-labeled celecoxib derivative
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38601
_journal_page_last               38611
_journal_paper_doi               10.1039/D0RA04494F
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 F N2 O2 S'
_chemical_formula_sum            'C18 H17 F N2 O2 S'
_chemical_formula_weight         344.39
_chemical_melting_point          100.5(10)
_chemical_name_systematic
;
3-(2-Fluoroethyl)-1-(4-(methylsulfonyl)phenyl)-5-phenyl-1H-pyrazole
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-10-26 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                92.663(1)
_cell_angle_beta                 105.904(1)
_cell_angle_gamma                115.409(1)
_cell_formula_units_Z            4
_cell_length_a                   11.2831(3)
_cell_length_b                   11.9926(3)
_cell_length_c                   14.2709(4)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      36.88
_cell_measurement_theta_min      3.07
_cell_volume                     1647.31(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker-Nonius APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            59598
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.903
_diffrn_reflns_theta_min         1.914
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7472
_exptl_transmission_factor_min   0.7104
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         16365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0616P)²+0.3394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13574
_reflns_number_total             16365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04494f2.cif
_cod_data_source_block           CG1415
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '99.5-101.5' was changed to
'100.5(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7241423
_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   0.928
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2014-1
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
N1 N 0.81108(6) 0.40706(6) 0.35697(5) 0.01568(10) Uani 1 1 d . . . . .
N2 N 0.69524(7) 0.35854(6) 0.38569(5) 0.01718(11) Uani 1 1 d . . . . .
C1 C 0.63777(7) 0.23498(7) 0.35517(6) 0.01753(12) Uani 1 1 d . . . . .
C2 C 0.71527(8) 0.20222(7) 0.30693(6) 0.01834(12) Uani 1 1 d . . . . .
H2A H 0.6957 0.1201 0.2793 0.022 Uiso 1 1 calc R U . . .
C3 C 0.82526(7) 0.31417(7) 0.30821(5) 0.01618(11) Uani 1 1 d . . . . .
C4 C 0.50711(8) 0.15015(8) 0.37486(7) 0.02174(14) Uani 1 1 d . . . . .
H4A H 0.4531 0.1963 0.3775 0.026 Uiso 1 1 calc R U . . .
H4B H 0.5317 0.1266 0.4403 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41854(9) 0.03283(9) 0.29677(8) 0.02826(17) Uani 1 1 d . . . . .
H5A H 0.4736 -0.0111 0.2903 0.034 Uiso 1 1 calc R U . . .
H5B H 0.3389 -0.0245 0.3162 0.034 Uiso 1 1 calc R U . . .
F1 F 0.36991(7) 0.06484(7) 0.20544(5) 0.04147(16) Uani 1 1 d . . . . .
C6 C 0.89993(7) 0.53827(6) 0.38639(5) 0.01494(11) Uani 1 1 d . . . . .
C7 C 0.84288(7) 0.61719(7) 0.40337(6) 0.01731(12) Uani 1 1 d . . . . .
H7A H 0.7464 0.5830 0.3941 0.021 Uiso 1 1 calc R U . . .
C8 C 0.92809(8) 0.74588(7) 0.43396(6) 0.01817(12) Uani 1 1 d . . . . .
H8A H 0.8908 0.8001 0.4471 0.022 Uiso 1 1 calc R U . . .
C9 C 1.06913(7) 0.79484(7) 0.44530(5) 0.01628(11) Uani 1 1 d . . . . .
C10 C 1.12586(7) 0.71670(7) 0.42792(6) 0.01661(11) Uani 1 1 d . . . . .
H10B H 1.2216 0.7514 0.4349 0.020 Uiso 1 1 calc R U . . .
C11 C 1.04176(7) 0.58739(7) 0.40028(6) 0.01641(11) Uani 1 1 d . . . . .
H11A H 1.0804 0.5329 0.3909 0.020 Uiso 1 1 calc R U . . .
S1 S 1.17910(2) 0.95753(2) 0.48764(2) 0.01786(4) Uani 1 1 d . . . . .
O1 O 1.14836(7) 0.99732(6) 0.57119(5) 0.02423(12) Uani 1 1 d . . . . .
O2 O 1.31966(6) 0.98035(6) 0.50171(5) 0.02468(12) Uani 1 1 d . . . . .
C12 C 1.12957(9) 1.02947(8) 0.38968(7) 0.02395(15) Uani 1 1 d . . . . .
H12A H 1.1873 1.1208 0.4086 0.036 Uiso 1 1 calc R U . . .
H12B H 1.0318 1.0093 0.3757 0.036 Uiso 1 1 calc R U . . .
H12C H 1.1421 0.9983 0.3303 0.036 Uiso 1 1 calc R U . . .
C13 C 0.92994(8) 0.33368(7) 0.25913(6) 0.01723(12) Uani 1 1 d . . . . .
C14 C 0.95134(8) 0.41495(8) 0.19130(6) 0.02028(13) Uani 1 1 d . . . . .
H14A H 0.8999 0.4610 0.1778 0.024 Uiso 1 1 calc R U . . .
C15 C 1.04775(10) 0.42867(9) 0.14348(7) 0.02611(16) Uani 1 1 d . . . . .
H15A H 1.0625 0.4845 0.0980 0.031 Uiso 1 1 calc R U . . .
C16 C 1.12255(10) 0.36064(9) 0.16226(9) 0.03050(19) Uani 1 1 d . . . . .
H16A H 1.1885 0.3702 0.1298 0.037 Uiso 1 1 calc R U . . .
C17 C 1.10047(11) 0.27903(10) 0.22844(9) 0.03163(19) Uani 1 1 d . . . . .
H17A H 1.1513 0.2324 0.2411 0.038 Uiso 1 1 calc R U . . .
C18 C 1.00422(9) 0.26476(8) 0.27669(7) 0.02488(15) Uani 1 1 d . . . . .
H18A H 0.9892 0.2081 0.3216 0.030 Uiso 1 1 calc R U . . .
N3 N 0.60361(7) 0.56925(7) 0.18171(5) 0.01904(11) Uani 1 1 d . . . . .
N4 N 0.50379(8) 0.53195(9) 0.22716(6) 0.02585(15) Uani 1 1 d . . . . .
C21 C 0.51892(9) 0.63840(12) 0.27385(7) 0.0307(2) Uani 1 1 d . . . . .
C22 C 0.62662(9) 0.74419(10) 0.25933(7) 0.02750(17) Uani 1 1 d . . . . .
H22A H 0.6564 0.8299 0.2847 0.033 Uiso 1 1 calc R U . . .
C23 C 0.68024(8) 0.69804(8) 0.20060(6) 0.01976(13) Uani 1 1 d . . . . .
C24A C 0.43241(16) 0.6457(2) 0.33470(12) 0.0317(3) Uani 0.781(3) 1 d . . P A 1
H24A H 0.3327 0.5976 0.2953 0.038 Uiso 0.781(3) 1 d R U P A 1
H24B H 0.4535 0.7344 0.3532 0.038 Uiso 0.781(3) 1 d R U P A 1
C25A C 0.46302(17) 0.59315(14) 0.42771(11) 0.0378(4) Uani 0.781(3) 1 d . . P A
1
H25A H 0.4519 0.5076 0.4102 0.045 Uiso 0.781(3) 1 d R U P A 1
H25B H 0.3980 0.5882 0.4638 0.045 Uiso 0.781(3) 1 d R U P A 1
F2A F 0.60120(8) 0.67489(9) 0.48756(5) 0.04774(19) Uani 0.781(3) 1 d . . P A 1
C24B C 0.4158(5) 0.5965(5) 0.3355(4) 0.0221(9) Uani 0.219(3) 1 d . . P A 2
H24C H 0.3270 0.5874 0.2964 0.026 Uiso 0.219(3) 1 d R U P A 2
H24D H 0.4040 0.5177 0.3548 0.026 Uiso 0.219(3) 1 d R U P A 2
C25B C 0.4766(4) 0.6964(4) 0.4225(3) 0.0237(9) Uani 0.219(3) 1 d . . P A 2
H25C H 0.5098 0.7781 0.4050 0.028 Uiso 0.219(3) 1 d R U P A 2
H25D H 0.4115 0.6872 0.4568 0.028 Uiso 0.219(3) 1 d R U P A 2
F2B F 0.60120(8) 0.67489(9) 0.48756(5) 0.04774(19) Uani 0.219(3) 1 d . . P A 2
C26 C 0.60698(7) 0.47573(7) 0.11986(5) 0.01691(12) Uani 1 1 d . . . . .
C27 C 0.55772(8) 0.35371(8) 0.13929(6) 0.02128(13) Uani 1 1 d . . . . .
H27A H 0.5236 0.3349 0.1935 0.026 Uiso 1 1 calc R U . . .
C28 C 0.55874(9) 0.25992(8) 0.07921(6) 0.02200(14) Uani 1 1 d . . . . .
H28A H 0.5237 0.1764 0.0912 0.026 Uiso 1 1 calc R U . . .
C29 C 0.61167(8) 0.28943(7) 0.00101(6) 0.01872(12) Uani 1 1 d . . . . .
C30 C 0.65900(8) 0.41029(7) -0.01959(6) 0.01772(12) Uani 1 1 d . . . . .
H30A H 0.6943 0.4291 -0.0733 0.021 Uiso 1 1 calc R U . . .
C31 C 0.65435(8) 0.50329(7) 0.03872(6) 0.01729(12) Uani 1 1 d . . . . .
H31A H 0.6832 0.5853 0.0236 0.021 Uiso 1 1 calc R U . . .
S2 S 0.61776(2) 0.17284(2) -0.07477(2) 0.02131(4) Uani 1 1 d . . . . .
O3 O 0.48078(7) 0.06678(6) -0.11227(6) 0.02775(13) Uani 1 1 d . . . . .
O4 O 0.68392(7) 0.23134(7) -0.14503(5) 0.02735(13) Uani 1 1 d . . . . .
C32 C 0.72685(10) 0.12448(9) 0.00747(8) 0.02872(18) Uani 1 1 d . . . . .
H32A H 0.7355 0.0588 -0.0293 0.043 Uiso 1 1 calc R U . . .
H32B H 0.6869 0.0914 0.0591 0.043 Uiso 1 1 calc R U . . .
H32C H 0.8188 0.1964 0.0382 0.043 Uiso 1 1 calc R U . . .
C33 C 0.80204(8) 0.77085(7) 0.17072(6) 0.01888(12) Uani 1 1 d . . . . .
C34 C 0.91019(8) 0.73872(8) 0.18290(6) 0.02019(13) Uani 1 1 d . . . . .
H34A H 0.9046 0.6660 0.2093 0.024 Uiso 1 1 calc R U . . .
C35 C 1.02569(9) 0.81278(9) 0.15656(7) 0.02482(15) Uani 1 1 d . . . . .
H35A H 1.0979 0.7897 0.1636 0.030 Uiso 1 1 calc R U . . .
C36 C 1.03534(10) 0.92089(10) 0.11984(8) 0.02947(18) Uani 1 1 d . . . . .
H36A H 1.1142 0.9716 0.1019 0.035 Uiso 1 1 calc R U . . .
C37 C 0.92956(10) 0.95444(9) 0.10942(8) 0.03058(18) Uani 1 1 d . . . . .
H37A H 0.9368 1.0287 0.0851 0.037 Uiso 1 1 calc R U . . .
C38 C 0.81330(9) 0.87998(8) 0.13439(7) 0.02549(16) Uani 1 1 d . . . . .
H38A H 0.7411 0.9033 0.1268 0.031 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1265 0.1256 '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
N2 N1 C3 111.65(6) . .
N2 N1 C6 117.64(6) . .
C3 N1 C6 130.54(6) . .
C1 N2 N1 105.00(6) . .
N2 C1 C2 111.52(7) . .
N2 C1 C4 119.86(7) . .
C2 C1 C4 128.62(7) . .
C3 C2 C1 105.62(7) . .
C3 C2 H2A 127.2 . .
C1 C2 H2A 127.2 . .
N1 C3 C2 106.20(6) . .
N1 C3 C13 125.99(6) . .
C2 C3 C13 127.56(7) . .
C1 C4 C5 112.35(7) . .
C1 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
C1 C4 H4B 109.1 . .
C5 C4 H4B 109.1 . .
H4A C4 H4B 107.9 . .
F1 C5 C4 109.45(8) . .
F1 C5 H5A 109.8 . .
C4 C5 H5A 109.8 . .
F1 C5 H5B 109.8 . .
C4 C5 H5B 109.8 . .
H5A C5 H5B 108.2 . .
C11 C6 C7 120.72(6) . .
C11 C6 N1 120.83(6) . .
C7 C6 N1 118.44(6) . .
C8 C7 C6 119.60(7) . .
C8 C7 H7A 120.2 . .
C6 C7 H7A 120.2 . .
C7 C8 C9 119.45(7) . .
C7 C8 H8A 120.3 . .
C9 C8 H8A 120.3 . .
C10 C9 C8 121.03(7) . .
C10 C9 S1 119.15(5) . .
C8 C9 S1 119.75(6) . .
C9 C10 C11 119.71(7) . .
C9 C10 H10B 120.1 . .
C11 C10 H10B 120.1 . .
C10 C11 C6 119.44(7) . .
C10 C11 H11A 120.3 . .
C6 C11 H11A 120.3 . .
O2 S1 O1 118.17(4) . .
O2 S1 C12 108.45(4) . .
O1 S1 C12 107.97(4) . .
O2 S1 C9 108.17(4) . .
O1 S1 C9 108.02(4) . .
C12 S1 C9 105.36(4) . .
S1 C12 H12A 109.5 . .
S1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
S1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C18 C13 C14 119.22(7) . .
C18 C13 C3 119.29(7) . .
C14 C13 C3 121.40(7) . .
C15 C14 C13 120.30(8) . .
C15 C14 H14A 119.9 . .
C13 C14 H14A 119.9 . .
C16 C15 C14 120.11(8) . .
C16 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
C17 C16 C15 119.76(8) . .
C17 C16 H16A 120.1 . .
C15 C16 H16A 120.1 . .
C16 C17 C18 120.53(9) . .
C16 C17 H17A 119.7 . .
C18 C17 H17A 119.7 . .
C17 C18 C13 120.07(8) . .
C17 C18 H18A 120.0 . .
C13 C18 H18A 120.0 . .
N4 N3 C23 111.39(7) . .
N4 N3 C26 118.01(7) . .
C23 N3 C26 130.45(7) . .
C21 N4 N3 104.87(8) . .
N4 C21 C22 111.71(8) . .
N4 C21 C24A 124.68(13) . .
C22 C21 C24A 123.61(12) . .
N4 C21 C24B 105.3(2) . .
C22 C21 C24B 142.5(2) . .
C23 C22 C21 105.71(9) . .
C23 C22 H22A 127.1 . .
C21 C22 H22A 127.1 . .
N3 C23 C22 106.32(8) . .
N3 C23 C33 126.63(7) . .
C22 C23 C33 126.88(8) . .
C21 C24A C25A 110.00(14) . .
C21 C24A H24A 109.8 . .
C25A C24A H24A 109.8 . .
C21 C24A H24B 109.5 . .
C25A C24A H24B 109.5 . .
H24A C24A H24B 108.1 . .
F2A C25A C24A 107.59(12) . .
F2A C25A H25A 110.4 . .
C24A C25A H25A 110.1 . .
F2A C25A H25B 110.2 . .
C24A C25A H25B 110.1 . .
H25A C25A H25B 108.5 . .
C25B C24B C21 106.4(3) . .
C25B C24B H24C 110.0 . .
C21 C24B H24C 109.9 . .
C25B C24B H24D 111.0 . .
C21 C24B H24D 110.8 . .
H24C C24B H24D 108.8 . .
C24B C25B H25C 111.6 . .
C24B C25B H25D 111.6 . .
H25C C25B H25D 109.2 . .
C27 C26 C31 120.33(7) . .
C27 C26 N3 118.70(7) . .
C31 C26 N3 120.94(7) . .
C28 C27 C26 119.86(7) . .
C28 C27 H27A 120.1 . .
C26 C27 H27A 120.1 . .
C27 C28 C29 119.42(7) . .
C27 C28 H28A 120.3 . .
C29 C28 H28A 120.3 . .
C30 C29 C28 120.97(7) . .
C30 C29 S2 118.67(6) . .
C28 C29 S2 120.35(6) . .
C31 C30 C29 119.62(7) . .
C31 C30 H30A 120.2 . .
C29 C30 H30A 120.2 . .
C30 C31 C26 119.70(7) . .
C30 C31 H31A 120.2 . .
C26 C31 H31A 120.2 . .
O4 S2 O3 118.47(4) . .
O4 S2 C29 108.14(4) . .
O3 S2 C29 108.63(4) . .
O4 S2 C32 108.72(5) . .
O3 S2 C32 107.64(4) . .
C29 S2 C32 104.36(4) . .
S2 C32 H32A 109.5 . .
S2 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
S2 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C38 C33 C34 119.24(8) . .
C38 C33 C23 118.37(7) . .
C34 C33 C23 122.28(7) . .
C35 C34 C33 120.30(8) . .
C35 C34 H34A 119.8 . .
C33 C34 H34A 119.8 . .
C34 C35 C36 119.93(8) . .
C34 C35 H35A 120.0 . .
C36 C35 H35A 120.0 . .
C37 C36 C35 119.97(9) . .
C37 C36 H36A 120.0 . .
C35 C36 H36A 120.0 . .
C38 C37 C36 120.32(9) . .
C38 C37 H37A 119.8 . .
C36 C37 H37A 119.8 . .
C37 C38 C33 120.23(8) . .
C37 C38 H38A 119.9 . .
C33 C38 H38A 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N2 1.3705(9) .
N1 C3 1.3757(10) .
N1 C6 1.4183(9) .
N2 C1 1.3291(10) .
C1 C2 1.4116(11) .
C1 C4 1.5013(11) .
C2 C3 1.3778(10) .
C2 H2A 0.9500 .
C3 C13 1.4738(10) .
C4 C5 1.5025(13) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 F1 1.4080(13) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C11 1.3977(10) .
C6 C7 1.3985(10) .
C7 C8 1.3896(10) .
C7 H7A 0.9500 .
C8 C9 1.3970(10) .
C8 H8A 0.9500 .
C9 C10 1.3890(10) .
C9 S1 1.7645(7) .
C10 C11 1.3915(10) .
C10 H10B 0.9500 .
C11 H11A 0.9500 .
S1 O2 1.4416(7) .
S1 O1 1.4441(7) .
S1 C12 1.7631(9) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C18 1.3953(11) .
C13 C14 1.3998(11) .
C14 C15 1.3927(12) .
C14 H14A 0.9500 .
C15 C16 1.3916(15) .
C15 H15A 0.9500 .
C16 C17 1.3848(15) .
C16 H16A 0.9500 .
C17 C18 1.3943(13) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
N3 N4 1.3727(10) .
N3 C23 1.3760(11) .
N3 C26 1.4147(10) .
N4 C21 1.3320(14) .
C21 C22 1.4031(16) .
C21 C24A 1.4986(16) .
C21 C24B 1.575(4) .
C22 C23 1.3772(11) .
C22 H22A 0.9500 .
C23 C33 1.4694(11) .
C24A C25A 1.514(3) .
C24A H24A 0.9900 .
C24A H24B 0.9900 .
C25A F2A 1.4149(18) .
C25A H25A 0.9901 .
C25A H25B 0.9899 .
C24B C25B 1.462(7) .
C24B H24C 0.9600 .
C24B H24D 0.9600 .
C25B H25C 0.9600 .
C25B H25D 0.9601 .
C26 C27 1.3969(11) .
C26 C31 1.3996(10) .
C27 C28 1.3883(13) .
C27 H27A 0.9500 .
C28 C29 1.3957(12) .
C28 H28A 0.9500 .
C29 C30 1.3906(11) .
C29 S2 1.7640(8) .
C30 C31 1.3882(11) .
C30 H30A 0.9500 .
C31 H31A 0.9500 .
S2 O4 1.4425(8) .
S2 O3 1.4456(7) .
S2 C32 1.7644(9) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 C38 1.3980(12) .
C33 C34 1.4003(11) .
C34 C35 1.3909(12) .
C34 H34A 0.9500 .
C35 C36 1.3931(14) .
C35 H35A 0.9500 .
C36 C37 1.3889(15) .
C36 H36A 0.9500 .
C37 C38 1.3876(14) .
C37 H37A 0.9500 .
C38 H38A 0.9500 .
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
C4 H4B O2 0.99 2.51 3.2198(11) 128.0 2_766
C12 H12A F2A 0.98 2.57 3.4830(12) 155.1 2_776
C12 H12B O1 0.98 2.33 3.2189(11) 150.5 2_776
C22 H22A O1 0.95 2.57 3.3301(11) 137.7 2_776
C25A H25A F2A 0.99 2.63 3.3411(19) 128.7 2_666
C32 H32A F1 0.98 2.54 3.3154(13) 136.3 2_655
C32 H32B O3 0.98 2.36 3.2579(13) 151.2 2_655
