#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227769.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_2227769
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 4-{2-[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]thiazol-4-yl}benzonitrile
;
_journal_coeditor_code           LH5111
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2286
_journal_page_last               o2287
_journal_paper_doi               10.1107/S1600536810031405
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H14 Cl F N4 S'
_chemical_formula_moiety         'C25 H14 Cl F N4 S'
_chemical_formula_sum            'C25 H14 Cl F N4 S'
_chemical_formula_weight         456.91
_chemical_name_systematic
;
4-{2-[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]thiazol-
4-yl}benzonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.518(2)
_cell_angle_beta                 107.869(2)
_cell_angle_gamma                99.253(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1412(9)
_cell_length_b                   15.0496(14)
_cell_length_c                   15.8890(14)
_cell_measurement_reflns_used    8583
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.74
_cell_volume                     2144.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44680
_diffrn_reflns_theta_full        30.18
_diffrn_reflns_theta_max         30.18
_diffrn_reflns_theta_min         1.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.500
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         12570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.5673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                9300
_reflns_number_total             12570
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5111.cif
_cod_data_source_block           I
_cod_database_code               2227769
_cod_database_fobs_code          2227769
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.65750(6) 0.27225(3) 0.07240(3) 0.04616(13) Uani d . 1 . .
S S1A 1.13306(4) 1.04182(3) 0.40859(3) 0.02482(8) Uani d . 1 . .
F F1A 1.42149(12) 0.59713(9) 0.08545(7) 0.0464(3) Uani d . 1 . .
N N1A 1.06028(13) 0.73997(8) 0.25101(9) 0.0217(2) Uani d . 1 . .
N N2A 1.09248(13) 0.83652(8) 0.29256(9) 0.0229(3) Uani d . 1 . .
N N3A 0.86452(14) 0.97158(9) 0.37237(9) 0.0233(3) Uani d . 1 . .
N N4A 0.37277(16) 1.24996(10) 0.53307(12) 0.0402(4) Uani d . 1 . .
C C1A 0.95272(17) 0.52359(11) 0.21546(11) 0.0248(3) Uani d . 1 . .
H H1AA 1.0519 0.5452 0.2463 0.030 Uiso calc R 1 . .
C C2A 0.88712(18) 0.42599(11) 0.17403(11) 0.0284(3) Uani d . 1 . .
H H2AA 0.9423 0.3823 0.1763 0.034 Uiso calc R 1 . .
C C3A 0.73902(19) 0.39404(11) 0.12930(11) 0.0312(4) Uani d . 1 . .
C C4A 0.65433(18) 0.45760(12) 0.12679(12) 0.0324(4) Uani d . 1 . .
H H4AA 0.5548 0.4354 0.0986 0.039 Uiso calc R 1 . .
C C5A 0.72013(17) 0.55472(12) 0.16696(11) 0.0290(3) Uani d . 1 . .
H H5AA 0.6640 0.5979 0.1648 0.035 Uiso calc R 1 . .
C C6A 0.87003(16) 0.58924(10) 0.21090(10) 0.0229(3) Uani d . 1 . .
C C7A 0.93212(15) 0.69361(10) 0.25151(10) 0.0220(3) Uani d . 1 . .
C C8A 0.88014(16) 0.76421(11) 0.29533(11) 0.0242(3) Uani d . 1 . .
H H8AA 0.7953 0.7563 0.3069 0.029 Uiso calc R 1 . .
C C9A 0.98191(16) 0.85051(10) 0.31872(10) 0.0222(3) Uani d . 1 . .
C C10A 0.97933(16) 0.94805(10) 0.36358(10) 0.0225(3) Uani d . 1 . .
C C11A 1.03671(16) 1.11797(11) 0.44212(10) 0.0241(3) Uani d . 1 . .
H H11A 1.0741 1.1836 0.4728 0.029 Uiso calc R 1 . .
C C12A 0.89653(16) 1.06938(10) 0.41774(10) 0.0227(3) Uani d . 1 . .
C C13A 0.78227(16) 1.11019(10) 0.43729(10) 0.0231(3) Uani d . 1 . .
C C14A 0.64515(18) 1.05103(12) 0.41109(12) 0.0331(4) Uani d . 1 . .
H H14B 0.6257 0.9860 0.3792 0.040 Uiso calc R 1 . .
C C15A 0.53762(18) 1.08749(12) 0.43178(13) 0.0357(4) Uani d . 1 . .
H H15B 0.4465 1.0473 0.4135 0.043 Uiso calc R 1 . .
C C16A 0.56653(17) 1.18491(11) 0.48025(11) 0.0275(3) Uani d . 1 . .
C C17A 0.70275(18) 1.24542(11) 0.50599(11) 0.0283(3) Uani d . 1 . .
H H17B 0.7219 1.3105 0.5376 0.034 Uiso calc R 1 . .
C C18A 0.80874(18) 1.20810(11) 0.48427(11) 0.0276(3) Uani d . 1 . .
H H18B 0.8990 1.2486 0.5011 0.033 Uiso calc R 1 . .
C C19A 0.45761(17) 1.22203(11) 0.50766(12) 0.0311(4) Uani d . 1 . .
C C20A 1.15274(15) 0.70276(10) 0.20723(10) 0.0211(3) Uani d . 1 . .
C C21A 1.29851(17) 0.72700(12) 0.25942(11) 0.0282(3) Uani d . 1 . .
H H21B 1.3348 0.7669 0.3218 0.034 Uiso calc R 1 . .
C C22A 1.39029(18) 0.69147(13) 0.21811(12) 0.0333(4) Uani d . 1 . .
H H22B 1.4884 0.7068 0.2521 0.040 Uiso calc R 1 . .
C C23A 1.33238(18) 0.63320(13) 0.12600(12) 0.0310(4) Uani d . 1 . .
C C24A 1.18802(18) 0.60842(12) 0.07246(11) 0.0294(3) Uani d . 1 . .
H H24B 1.1524 0.5684 0.0102 0.035 Uiso calc R 1 . .
C C25A 1.09718(16) 0.64470(11) 0.11382(10) 0.0243(3) Uani d . 1 . .
H H25B 0.9995 0.6302 0.0790 0.029 Uiso calc R 1 . .
Cl Cl1B 0.76527(5) -0.39437(3) -0.11384(3) 0.04333(12) Uani d . 1 . .
S S1B 1.14106(4) 0.33994(3) 0.36702(3) 0.02914(9) Uani d . 1 . .
F F1B 1.57725(11) -0.05590(8) 0.10753(9) 0.0484(3) Uani d . 1 . .
N N1B 1.13119(13) 0.06398(8) 0.18871(9) 0.0212(2) Uani d . 1 . .
N N2B 1.14761(13) 0.15432(8) 0.24368(9) 0.0224(2) Uani d . 1 . .
N N3B 0.86803(13) 0.25950(8) 0.29038(8) 0.0216(2) Uani d . 1 . .
N N4B 0.31537(16) 0.53818(10) 0.35928(12) 0.0417(4) Uani d . 1 . .
C C1B 0.99178(17) -0.12120(11) 0.01556(10) 0.0251(3) Uani d . 1 . .
H H1BA 1.0637 -0.0792 0.0097 0.030 Uiso calc R 1 . .
C C2B 0.93788(18) -0.21482(11) -0.04635(11) 0.0286(3) Uani d . 1 . .
H H2BA 0.9740 -0.2358 -0.0931 0.034 Uiso calc R 1 . .
C C3B 0.82978(18) -0.27638(11) -0.03761(11) 0.0287(3) Uani d . 1 . .
C C4B 0.77397(17) -0.24687(11) 0.03145(12) 0.0284(3) Uani d . 1 . .
H H4BA 0.7011 -0.2890 0.0363 0.034 Uiso calc R 1 . .
C C5B 0.82882(16) -0.15338(10) 0.09319(11) 0.0246(3) Uani d . 1 . .
H H5BA 0.7920 -0.1328 0.1397 0.029 Uiso calc R 1 . .
C C6B 0.93883(16) -0.08956(10) 0.08655(10) 0.0220(3) Uani d . 1 . .
C C7B 0.99122(16) 0.00952(10) 0.15263(10) 0.0212(3) Uani d . 1 . .
C C8B 0.91412(16) 0.06778(10) 0.18710(10) 0.0230(3) Uani d . 1 . .
H H8BA 0.8164 0.0520 0.1760 0.028 Uiso calc R 1 . .
C C9B 1.01516(16) 0.15581(10) 0.24242(10) 0.0219(3) Uani d . 1 . .
C C10B 0.99350(16) 0.24426(10) 0.29498(10) 0.0218(3) Uani d . 1 . .
C C11B 1.02670(17) 0.40573(11) 0.39097(11) 0.0267(3) Uani d . 1 . .
H H11B 1.0558 0.4691 0.4303 0.032 Uiso calc R 1 . .
C C12B 0.88655(16) 0.35308(10) 0.34484(10) 0.0220(3) Uani d . 1 . .
C C13B 0.76062(16) 0.38949(10) 0.34638(10) 0.0217(3) Uani d . 1 . .
C C14B 0.62431(17) 0.32800(10) 0.31896(11) 0.0255(3) Uani d . 1 . .
H H14A 0.6121 0.2622 0.2988 0.031 Uiso calc R 1 . .
C C15B 0.50724(17) 0.36374(11) 0.32137(12) 0.0289(3) Uani d . 1 . .
H H15A 0.4171 0.3223 0.3030 0.035 Uiso calc R 1 . .
C C16B 0.52600(17) 0.46296(11) 0.35171(11) 0.0258(3) Uani d . 1 . .
C C17B 0.66100(17) 0.52504(10) 0.37804(11) 0.0262(3) Uani d . 1 . .
H H17A 0.6732 0.5908 0.3977 0.031 Uiso calc R 1 . .
C C18B 0.77587(17) 0.48827(10) 0.37473(11) 0.0252(3) Uani d . 1 . .
H H18A 0.8654 0.5298 0.3916 0.030 Uiso calc R 1 . .
C C19B 0.40724(18) 0.50352(11) 0.35543(12) 0.0314(4) Uani d . 1 . .
C C20B 1.25363(15) 0.03680(10) 0.17432(10) 0.0216(3) Uani d . 1 . .
C C21B 1.33796(17) 0.09201(11) 0.14291(12) 0.0284(3) Uani d . 1 . .
H H21A 1.3194 0.1487 0.1358 0.034 Uiso calc R 1 . .
C C22B 1.45039(18) 0.06178(12) 0.12222(14) 0.0355(4) Uani d . 1 . .
H H22A 1.5097 0.0982 0.1023 0.043 Uiso calc R 1 . .
C C23B 1.47150(17) -0.02352(12) 0.13207(13) 0.0321(4) Uani d . 1 . .
C C24B 1.39172(17) -0.07789(11) 0.16568(12) 0.0303(3) Uani d . 1 . .
H H24A 1.4112 -0.1342 0.1731 0.036 Uiso calc R 1 . .
C C25B 1.28151(16) -0.04656(11) 0.18819(11) 0.0258(3) Uani d . 1 . .
H H25A 1.2270 -0.0810 0.2123 0.031 Uiso calc R 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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
C11A S1A C10A . . 89.00(7) ?
N2A N1A C7A . . 112.26(11) ?
N2A N1A C20A . . 117.81(11) ?
C7A N1A C20A . . 129.66(12) ?
C9A N2A N1A . . 104.36(12) ?
C10A N3A C12A . . 110.04(13) ?
C2A C1A C6A . . 120.19(15) ?
C2A C1A H1AA . . 119.9 ?
C6A C1A H1AA . . 119.9 ?
C3A C2A C1A . . 119.69(15) ?
C3A C2A H2AA . . 120.2 ?
C1A C2A H2AA . . 120.2 ?
C4A C3A C2A . . 121.18(15) ?
C4A C3A Cl1A . . 119.05(13) ?
C2A C3A Cl1A . . 119.75(14) ?
C5A C4A C3A . . 118.95(15) ?
C5A C4A H4AA . . 120.5 ?
C3A C4A H4AA . . 120.5 ?
C4A C5A C6A . . 121.13(15) ?
C4A C5A H5AA . . 119.4 ?
C6A C5A H5AA . . 119.4 ?
C1A C6A C5A . . 118.80(14) ?
C1A C6A C7A . . 123.26(13) ?
C5A C6A C7A . . 117.93(14) ?
N1A C7A C8A . . 105.87(13) ?
N1A C7A C6A . . 124.12(13) ?
C8A C7A C6A . . 130.00(13) ?
C7A C8A C9A . . 105.62(13) ?
C7A C8A H8AA . . 127.2 ?
C9A C8A H8AA . . 127.2 ?
N2A C9A C8A . . 111.89(13) ?
N2A C9A C10A . . 118.99(13) ?
C8A C9A C10A . . 129.10(13) ?
N3A C10A C9A . . 123.79(14) ?
N3A C10A S1A . . 115.43(11) ?
C9A C10A S1A . . 120.78(11) ?
C12A C11A S1A . . 110.82(11) ?
C12A C11A H11A . . 124.6 ?
S1A C11A H11A . . 124.6 ?
C11A C12A N3A . . 114.71(13) ?
C11A C12A C13A . . 126.63(14) ?
N3A C12A C13A . . 118.64(13) ?
C14A C13A C18A . . 118.52(14) ?
C14A C13A C12A . . 120.22(13) ?
C18A C13A C12A . . 121.24(14) ?
C15A C14A C13A . . 121.12(15) ?
C15A C14A H14B . . 119.4 ?
C13A C14A H14B . . 119.4 ?
C14A C15A C16A . . 119.65(16) ?
C14A C15A H15B . . 120.2 ?
C16A C15A H15B . . 120.2 ?
C15A C16A C17A . . 119.99(14) ?
C15A C16A C19A . . 119.77(15) ?
C17A C16A C19A . . 120.17(14) ?
C18A C17A C16A . . 119.70(14) ?
C18A C17A H17B . . 120.2 ?
C16A C17A H17B . . 120.2 ?
C17A C18A C13A . . 121.01(15) ?
C17A C18A H18B . . 119.5 ?
C13A C18A H18B . . 119.5 ?
N4A C19A C16A . . 176.7(2) ?
C25A C20A C21A . . 120.93(14) ?
C25A C20A N1A . . 120.26(13) ?
C21A C20A N1A . . 118.80(13) ?
C20A C21A C22A . . 119.68(15) ?
C20A C21A H21B . . 120.2 ?
C22A C21A H21B . . 120.2 ?
C23A C22A C21A . . 118.22(15) ?
C23A C22A H22B . . 120.9 ?
C21A C22A H22B . . 120.9 ?
F1A C23A C22A . . 118.52(15) ?
F1A C23A C24A . . 118.24(15) ?
C22A C23A C24A . . 123.24(15) ?
C23A C24A C25A . . 118.27(15) ?
C23A C24A H24B . . 120.9 ?
C25A C24A H24B . . 120.9 ?
C20A C25A C24A . . 119.63(14) ?
C20A C25A H25B . . 120.2 ?
C24A C25A H25B . . 120.2 ?
C11B S1B C10B . . 88.81(7) ?
N2B N1B C7B . . 112.35(11) ?
N2B N1B C20B . . 119.34(12) ?
C7B N1B C20B . . 128.31(12) ?
C9B N2B N1B . . 104.17(12) ?
C10B N3B C12B . . 109.82(12) ?
C2B C1B C6B . . 120.61(14) ?
C2B C1B H1BA . . 119.7 ?
C6B C1B H1BA . . 119.7 ?
C3B C2B C1B . . 119.22(15) ?
C3B C2B H2BA . . 120.4 ?
C1B C2B H2BA . . 120.4 ?
C2B C3B C4B . . 121.55(14) ?
C2B C3B Cl1B . . 119.01(13) ?
C4B C3B Cl1B . . 119.42(13) ?
C3B C4B C5B . . 118.84(15) ?
C3B C4B H4BA . . 120.6 ?
C5B C4B H4BA . . 120.6 ?
C4B C5B C6B . . 120.98(14) ?
C4B C5B H5BA . . 119.5 ?
C6B C5B H5BA . . 119.5 ?
C1B C6B C5B . . 118.80(13) ?
C1B C6B C7B . . 122.35(13) ?
C5B C6B C7B . . 118.81(13) ?
N1B C7B C8B . . 106.21(12) ?
N1B C7B C6B . . 124.85(13) ?
C8B C7B C6B . . 128.87(13) ?
C7B C8B C9B . . 105.04(13) ?
C7B C8B H8BA . . 127.5 ?
C9B C8B H8BA . . 127.5 ?
N2B C9B C8B . . 112.23(13) ?
N2B C9B C10B . . 118.76(13) ?
C8B C9B C10B . . 129.00(14) ?
N3B C10B C9B . . 125.06(13) ?
N3B C10B S1B . . 115.54(11) ?
C9B C10B S1B . . 119.37(11) ?
C12B C11B S1B . . 111.18(11) ?
C12B C11B H11B . . 124.4 ?
S1B C11B H11B . . 124.4 ?
C11B C12B N3B . . 114.62(13) ?
C11B C12B C13B . . 125.19(13) ?
N3B C12B C13B . . 120.14(13) ?
C14B C13B C18B . . 118.50(13) ?
C14B C13B C12B . . 121.88(13) ?
C18B C13B C12B . . 119.61(13) ?
C15B C14B C13B . . 120.98(14) ?
C15B C14B H14A . . 119.5 ?
C13B C14B H14A . . 119.5 ?
C14B C15B C16B . . 119.36(14) ?
C14B C15B H15A . . 120.3 ?
C16B C15B H15A . . 120.3 ?
C17B C16B C15B . . 120.22(14) ?
C17B C16B C19B . . 118.43(13) ?
C15B C16B C19B . . 121.34(14) ?
C18B C17B C16B . . 119.62(14) ?
C18B C17B H17A . . 120.2 ?
C16B C17B H17A . . 120.2 ?
C17B C18B C13B . . 121.30(14) ?
C17B C18B H18A . . 119.3 ?
C13B C18B H18A . . 119.3 ?
N4B C19B C16B . . 178.14(17) ?
C25B C20B C21B . . 121.52(13) ?
C25B C20B N1B . . 119.10(13) ?
C21B C20B N1B . . 119.32(13) ?
C20B C21B C22B . . 119.32(14) ?
C20B C21B H21A . . 120.3 ?
C22B C21B H21A . . 120.3 ?
C23B C22B C21B . . 118.09(15) ?
C23B C22B H22A . . 121.0 ?
C21B C22B H22A . . 121.0 ?
F1B C23B C22B . . 118.39(15) ?
F1B C23B C24B . . 118.19(14) ?
C22B C23B C24B . . 123.42(14) ?
C23B C24B C25B . . 118.34(14) ?
C23B C24B H24A . . 120.8 ?
C25B C24B H24A . . 120.8 ?
C24B C25B C20B . . 119.20(14) ?
C24B C25B H25A . . 120.4 ?
C20B C25B H25A . . 120.4 ?
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
Cl1A C3A . 1.7401(16) ?
S1A C11A . 1.7044(15) ?
S1A C10A . 1.7325(16) ?
F1A C23A . 1.3617(17) ?
N1A N2A . 1.3622(16) ?
N1A C7A . 1.3761(18) ?
N1A C20A . 1.4273(17) ?
N2A C9A . 1.3377(18) ?
N3A C10A . 1.3063(18) ?
N3A C12A . 1.3879(18) ?
N4A C19A . 1.148(2) ?
C1A C2A . 1.390(2) ?
C1A C6A . 1.397(2) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.386(2) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.385(2) ?
C4A C5A . 1.384(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.403(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.473(2) ?
C7A C8A . 1.379(2) ?
C8A C9A . 1.402(2) ?
C8A H8AA . 0.9300 ?
C9A C10A . 1.459(2) ?
C11A C12A . 1.372(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.471(2) ?
C13A C14A . 1.396(2) ?
C13A C18A . 1.401(2) ?
C14A C15A . 1.384(2) ?
C14A H14B . 0.9300 ?
C15A C16A . 1.396(2) ?
C15A H15B . 0.9300 ?
C16A C17A . 1.398(2) ?
C16A C19A . 1.444(2) ?
C17A C18A . 1.381(2) ?
C17A H17B . 0.9300 ?
C18A H18B . 0.9300 ?
C20A C25A . 1.385(2) ?
C20A C21A . 1.385(2) ?
C21A C22A . 1.389(2) ?
C21A H21B . 0.9300 ?
C22A C23A . 1.370(2) ?
C22A H22B . 0.9300 ?
C23A C24A . 1.377(2) ?
C24A C25A . 1.386(2) ?
C24A H24B . 0.9300 ?
C25A H25B . 0.9300 ?
Cl1B C3B . 1.7428(15) ?
S1B C11B . 1.7055(15) ?
S1B C10B . 1.7312(15) ?
F1B C23B . 1.3647(17) ?
N1B N2B . 1.3570(16) ?
N1B C7B . 1.3749(18) ?
N1B C20B . 1.4314(18) ?
N2B C9B . 1.3411(18) ?
N3B C10B . 1.3124(19) ?
N3B C12B . 1.3895(18) ?
N4B C19B . 1.148(2) ?
C1B C2B . 1.390(2) ?
C1B C6B . 1.398(2) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.384(2) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.387(2) ?
C4B C5B . 1.388(2) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.400(2) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.474(2) ?
C7B C8B . 1.3808(19) ?
C8B C9B . 1.402(2) ?
C8B H8BA . 0.9300 ?
C9B C10B . 1.459(2) ?
C11B C12B . 1.369(2) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.473(2) ?
C13B C14B . 1.400(2) ?
C13B C18B . 1.401(2) ?
C14B C15B . 1.387(2) ?
C14B H14A . 0.9300 ?
C15B C16B . 1.402(2) ?
C15B H15A . 0.9300 ?
C16B C17B . 1.397(2) ?
C16B C19B . 1.445(2) ?
C17B C18B . 1.377(2) ?
C17B H17A . 0.9300 ?
C18B H18A . 0.9300 ?
C20B C25B . 1.388(2) ?
C20B C21B . 1.388(2) ?
C21B C22B . 1.390(2) ?
C21B H21A . 0.9300 ?
C22B C23B . 1.376(2) ?
C22B H22A . 0.9300 ?
C23B C24B . 1.377(2) ?
C24B C25B . 1.387(2) ?
C24B H24A . 0.9300 ?
C25B H25A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5A H5AA F1A 1_455 0.93 2.39 3.149(2) 138 yes
C8B H8BA F1B 1_455 0.93 2.42 3.283(2) 154 yes
C17B H17A N4A 2_676 0.93 2.54 3.419(2) 159 yes
C17A H17B N4B 2_676 0.93 2.58 3.453(2) 156 yes
C25B H25A N2A 1_545 0.93 2.53 3.457(2) 175 yes
C24A H24B Cg1 2_765 0.93 2.96 3.7811(18) 148 yes
C21B H21A Cg2 2_755 0.93 2.97 3.6423(19) 131 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A N2A C9A . . . . -0.46(16) ?
C20A N1A N2A C9A . . . . 174.20(12) ?
C6A C1A C2A C3A . . . . -0.9(2) ?
C1A C2A C3A C4A . . . . -1.4(2) ?
C1A C2A C3A Cl1A . . . . 176.82(12) ?
C2A C3A C4A C5A . . . . 2.3(2) ?
Cl1A C3A C4A C5A . . . . -175.97(12) ?
C3A C4A C5A C6A . . . . -0.9(2) ?
C2A C1A C6A C5A . . . . 2.3(2) ?
C2A C1A C6A C7A . . . . -178.81(14) ?
C4A C5A C6A C1A . . . . -1.4(2) ?
C4A C5A C6A C7A . . . . 179.62(14) ?
N2A N1A C7A C8A . . . . 0.16(17) ?
C20A N1A C7A C8A . . . . -173.70(14) ?
N2A N1A C7A C6A . . . . 179.59(13) ?
C20A N1A C7A C6A . . . . 5.7(2) ?
C1A C6A C7A N1A . . . . 37.1(2) ?
C5A C6A C7A N1A . . . . -143.99(15) ?
C1A C6A C7A C8A . . . . -143.60(17) ?
C5A C6A C7A C8A . . . . 35.3(2) ?
N1A C7A C8A C9A . . . . 0.20(16) ?
C6A C7A C8A C9A . . . . -179.19(15) ?
N1A N2A C9A C8A . . . . 0.59(17) ?
N1A N2A C9A C10A . . . . -178.03(12) ?
C7A C8A C9A N2A . . . . -0.51(18) ?
C7A C8A C9A C10A . . . . 177.94(15) ?
C12A N3A C10A C9A . . . . -179.85(13) ?
C12A N3A C10A S1A . . . . -0.36(16) ?
N2A C9A C10A N3A . . . . 163.76(14) ?
C8A C9A C10A N3A . . . . -14.6(3) ?
N2A C9A C10A S1A . . . . -15.70(19) ?
C8A C9A C10A S1A . . . . 165.95(13) ?
C11A S1A C10A N3A . . . . 0.31(12) ?
C11A S1A C10A C9A . . . . 179.81(13) ?
C10A S1A C11A C12A . . . . -0.15(12) ?
S1A C11A C12A N3A . . . . -0.01(17) ?
S1A C11A C12A C13A . . . . 178.17(12) ?
C10A N3A C12A C11A . . . . 0.24(18) ?
C10A N3A C12A C13A . . . . -178.10(13) ?
C11A C12A C13A C14A . . . . -177.63(16) ?
N3A C12A C13A C14A . . . . 0.5(2) ?
C11A C12A C13A C18A . . . . 0.8(2) ?
N3A C12A C13A C18A . . . . 178.91(14) ?
C18A C13A C14A C15A . . . . -0.8(3) ?
C12A C13A C14A C15A . . . . 177.70(16) ?
C13A C14A C15A C16A . . . . -0.5(3) ?
C14A C15A C16A C17A . . . . 1.3(3) ?
C14A C15A C16A C19A . . . . -175.72(17) ?
C15A C16A C17A C18A . . . . -0.8(2) ?
C19A C16A C17A C18A . . . . 176.16(15) ?
C16A C17A C18A C13A . . . . -0.4(2) ?
C14A C13A C18A C17A . . . . 1.2(2) ?
C12A C13A C18A C17A . . . . -177.22(14) ?
N2A N1A C20A C25A . . . . -124.58(15) ?
C7A N1A C20A C25A . . . . 49.0(2) ?
N2A N1A C20A C21A . . . . 54.44(18) ?
C7A N1A C20A C21A . . . . -131.98(16) ?
C25A C20A C21A C22A . . . . -1.0(2) ?
N1A C20A C21A C22A . . . . 179.96(14) ?
C20A C21A C22A C23A . . . . 0.2(3) ?
C21A C22A C23A F1A . . . . -179.16(15) ?
C21A C22A C23A C24A . . . . 0.2(3) ?
F1A C23A C24A C25A . . . . 179.68(14) ?
C22A C23A C24A C25A . . . . 0.3(3) ?
C21A C20A C25A C24A . . . . 1.6(2) ?
N1A C20A C25A C24A . . . . -179.45(13) ?
C23A C24A C25A C20A . . . . -1.2(2) ?
C7B N1B N2B C9B . . . . 0.54(16) ?
C20B N1B N2B C9B . . . . -179.95(12) ?
C6B C1B C2B C3B . . . . 0.7(2) ?
C1B C2B C3B C4B . . . . 0.0(2) ?
C1B C2B C3B Cl1B . . . . -178.65(12) ?
C2B C3B C4B C5B . . . . -0.3(2) ?
Cl1B C3B C4B C5B . . . . 178.40(12) ?
C3B C4B C5B C6B . . . . -0.2(2) ?
C2B C1B C6B C5B . . . . -1.1(2) ?
C2B C1B C6B C7B . . . . -178.93(14) ?
C4B C5B C6B C1B . . . . 0.8(2) ?
C4B C5B C6B C7B . . . . 178.76(14) ?
N2B N1B C7B C8B . . . . -0.64(16) ?
C20B N1B C7B C8B . . . . 179.92(13) ?
N2B N1B C7B C6B . . . . 176.52(13) ?
C20B N1B C7B C6B . . . . -2.9(2) ?
C1B C6B C7B N1B . . . . -36.7(2) ?
C5B C6B C7B N1B . . . . 145.41(14) ?
C1B C6B C7B C8B . . . . 139.76(16) ?
C5B C6B C7B C8B . . . . -38.1(2) ?
N1B C7B C8B C9B . . . . 0.44(16) ?
C6B C7B C8B C9B . . . . -176.56(14) ?
N1B N2B C9B C8B . . . . -0.24(16) ?
N1B N2B C9B C10B . . . . -179.58(12) ?
C7B C8B C9B N2B . . . . -0.13(17) ?
C7B C8B C9B C10B . . . . 179.12(14) ?
C12B N3B C10B C9B . . . . -176.26(13) ?
C12B N3B C10B S1B . . . . 1.59(16) ?
N2B C9B C10B N3B . . . . 170.87(14) ?
C8B C9B C10B N3B . . . . -8.3(2) ?
N2B C9B C10B S1B . . . . -6.90(18) ?
C8B C9B C10B S1B . . . . 173.89(12) ?
C11B S1B C10B N3B . . . . -1.16(12) ?
C11B S1B C10B C9B . . . . 176.82(12) ?
C10B S1B C11B C12B . . . . 0.34(12) ?
S1B C11B C12B N3B . . . . 0.48(17) ?
S1B C11B C12B C13B . . . . -176.84(11) ?
C10B N3B C12B C11B . . . . -1.32(18) ?
C10B N3B C12B C13B . . . . 176.15(12) ?
C11B C12B C13B C14B . . . . -163.03(15) ?
N3B C12B C13B C14B . . . . 19.8(2) ?
C11B C12B C13B C18B . . . . 17.9(2) ?
N3B C12B C13B C18B . . . . -159.31(13) ?
C18B C13B C14B C15B . . . . -1.2(2) ?
C12B C13B C14B C15B . . . . 179.68(14) ?
C13B C14B C15B C16B . . . . 0.0(2) ?
C14B C15B C16B C17B . . . . 0.8(2) ?
C14B C15B C16B C19B . . . . -179.99(15) ?
C15B C16B C17B C18B . . . . -0.5(2) ?
C19B C16B C17B C18B . . . . -179.70(15) ?
C16B C17B C18B C13B . . . . -0.7(2) ?
C14B C13B C18B C17B . . . . 1.6(2) ?
C12B C13B C18B C17B . . . . -179.31(14) ?
N2B N1B C20B C25B . . . . 129.87(15) ?
C7B N1B C20B C25B . . . . -50.7(2) ?
N2B N1B C20B C21B . . . . -52.93(19) ?
C7B N1B C20B C21B . . . . 126.48(16) ?
C25B C20B C21B C22B . . . . 1.9(3) ?
N1B C20B C21B C22B . . . . -175.22(15) ?
C20B C21B C22B C23B . . . . 1.3(3) ?
C21B C22B C23B F1B . . . . 176.88(16) ?
C21B C22B C23B C24B . . . . -3.3(3) ?
F1B C23B C24B C25B . . . . -178.21(15) ?
C22B C23B C24B C25B . . . . 2.0(3) ?
C23B C24B C25B C20B . . . . 1.3(2) ?
C21B C20B C25B C24B . . . . -3.3(2) ?
N1B C20B C25B C24B . . . . 173.87(14) ?
