#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:16:27 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179369 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/66/4326606.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_4326606
loop_
_publ_author_name
'Purnandhu Bose'
'I. Ravikumar'
'Pradyut Ghosh'
_publ_section_title
;
 Anion Binding in the C3v-Symmetric Cavity of a Protonated Tripodal Amine
 Receptor: Potentiometric and Single Crystal X-ray Studies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10693
_journal_page_last               10702
_journal_paper_doi               10.1021/ic2011502
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C48 H45 F15 N4 O9 S3'
_chemical_formula_weight         1203.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.316(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3969(12)
_cell_length_b                   35.214(5)
_cell_length_c                   17.523(3)
_cell_measurement_reflns_used    3575
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.59
_cell_measurement_theta_min      2.31
_cell_volume                     5172.7(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'MERCURY 2.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0970
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48400
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         9090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0306P)²+4.2581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                5448
_reflns_number_total             9090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic2011502_si_004.cif
_cod_data_source_block           test1
_cod_original_cell_volume        5172.5(13)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4326606
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3102(4) 0.15566(11) 0.4264(2) 0.0407(10) Uani 1 1 d .
C3 C 0.1717(5) 0.14857(12) 0.3059(2) 0.0468(10) Uani 1 1 d .
C2 C 0.2632(5) 0.13359(11) 0.3648(3) 0.0488(11) Uani 1 1 d .
C4 C 0.1284(5) 0.18597(11) 0.3078(2) 0.0406(9) Uani 1 1 d .
C5 C 0.1777(4) 0.20761(10) 0.3692(2) 0.0345(9) Uani 1 1 d .
C6 C 0.2680(4) 0.19367(10) 0.43108(19) 0.0318(8) Uani 1 1 d .
C7 C 0.3263(4) 0.21798(10) 0.49775(19) 0.0343(9) Uani 1 1 d .
H7A H 0.4200 0.2062 0.5227 0.041 Uiso 1 1 calc R
H7B H 0.3578 0.2426 0.4788 0.041 Uiso 1 1 calc R
C8 C 0.2666(4) 0.24645(10) 0.62193(19) 0.0337(9) Uani 1 1 d .
H8A H 0.3250 0.2681 0.6039 0.040 Uiso 1 1 calc R
H8B H 0.3399 0.2311 0.6537 0.040 Uiso 1 1 calc R
C9 C 0.1329(4) 0.26016(10) 0.66901(19) 0.0375(9) Uani 1 1 d .
H9A H 0.1772 0.2768 0.7088 0.045 Uiso 1 1 calc R
H9B H 0.0591 0.2750 0.6365 0.045 Uiso 1 1 calc R
C10 C -0.1289(4) 0.23624(9) 0.69368(19) 0.0324(8) Uani 1 1 d .
H10A H -0.1552 0.2407 0.6398 0.039 Uiso 1 1 calc R
H10B H -0.1557 0.2590 0.7212 0.039 Uiso 1 1 calc R
C11 C -0.2298(4) 0.20387(9) 0.72016(19) 0.0332(9) Uani 1 1 d .
H11A H -0.2195 0.2022 0.7755 0.040 Uiso 1 1 calc R
H11B H -0.3410 0.2087 0.7052 0.040 Uiso 1 1 calc R
C12 C -0.2788(4) 0.13484(9) 0.7121(2) 0.0385(9) Uani 1 1 d .
H12A H -0.3882 0.1381 0.6922 0.046 Uiso 1 1 calc R
H12B H -0.2783 0.1347 0.7674 0.046 Uiso 1 1 calc R
C13 C -0.2158(4) 0.09771(10) 0.6849(2) 0.0355(9) Uani 1 1 d .
C14 C -0.1208(5) 0.07418(11) 0.7310(2) 0.0425(10) Uani 1 1 d .
C15 C -0.0620(5) 0.04044(11) 0.7055(3) 0.0558(12) Uani 1 1 d .
C16 C -0.0980(6) 0.02946(11) 0.6326(3) 0.0582(12) Uani 1 1 d .
C17 C -0.1916(5) 0.05149(12) 0.5852(2) 0.0550(12) Uani 1 1 d .
C18 C -0.2496(5) 0.08491(10) 0.6114(2) 0.0421(10) Uani 1 1 d .
C19 C 0.0868(4) 0.22548(10) 0.78694(18) 0.0350(9) Uani 1 1 d .
H19A H 0.0210 0.2058 0.8076 0.042 Uiso 1 1 calc R
H19B H 0.0631 0.2491 0.8125 0.042 Uiso 1 1 calc R
C20 C 0.2609(4) 0.21562(10) 0.80470(18) 0.0327(8) Uani 1 1 d .
H20A H 0.2929 0.1961 0.7696 0.039 Uiso 1 1 calc R
H20B H 0.3260 0.2379 0.7972 0.039 Uiso 1 1 calc R
C21 C 0.1924(4) 0.16788(10) 0.90401(19) 0.0362(9) Uani 1 1 d .
H21A H 0.1868 0.1508 0.8605 0.043 Uiso 1 1 calc R
H21B H 0.0847 0.1761 0.9128 0.043 Uiso 1 1 calc R
C22 C 0.2587(4) 0.14666(10) 0.97313(19) 0.0336(9) Uani 1 1 d .
C23 C 0.2886(4) 0.16353(10) 1.0432(2) 0.0368(9) Uani 1 1 d .
C24 C 0.3477(5) 0.14419(11) 1.1063(2) 0.0423(10) Uani 1 1 d .
C25 C 0.3731(5) 0.10595(12) 1.1014(2) 0.0512(11) Uani 1 1 d .
C26 C 0.3404(5) 0.08784(11) 1.0335(2) 0.0545(12) Uani 1 1 d .
C27 C 0.2865(5) 0.10812(11) 0.9708(2) 0.0474(10) Uani 1 1 d .
C28 C 0.5193(7) -0.02089(12) 0.6465(4) 0.128(3) Uani 1 1 d .
H28A H 0.4444 -0.0393 0.6258 0.192 Uiso 1 1 calc R
H28B H 0.5564 -0.0284 0.6971 0.192 Uiso 1 1 calc R
H28C H 0.6082 -0.0193 0.6146 0.192 Uiso 1 1 calc R
C29 C 0.4383(6) 0.01775(13) 0.6498(4) 0.0798(18) Uani 1 1 d .
C30 C 0.4389(6) 0.03774(13) 0.7174(3) 0.0780(16) Uani 1 1 d .
H30 H 0.4871 0.0272 0.7616 0.094 Uiso 1 1 calc R
C31 C 0.3680(5) 0.07355(11) 0.7204(3) 0.0556(12) Uani 1 1 d .
H31 H 0.3690 0.0867 0.7664 0.067 Uiso 1 1 calc R
C32 C 0.2971(4) 0.08926(10) 0.6558(2) 0.0383(9) Uani 1 1 d .
C33 C 0.2930(5) 0.06929(11) 0.5878(3) 0.0600(13) Uani 1 1 d .
H33 H 0.2430 0.0795 0.5437 0.072 Uiso 1 1 calc R
C34 C 0.3647(6) 0.03384(13) 0.5865(4) 0.0835(18) Uani 1 1 d .
H34 H 0.3624 0.0205 0.5406 0.100 Uiso 1 1 calc R
C35 C 0.8196(5) 0.06437(11) 0.2759(3) 0.0646(13) Uani 1 1 d .
H35A H 0.9275 0.0629 0.2607 0.097 Uiso 1 1 calc R
H35B H 0.7480 0.0659 0.2312 0.097 Uiso 1 1 calc R
H35C H 0.7954 0.0422 0.3047 0.097 Uiso 1 1 calc R
C36 C 0.8008(5) 0.09927(10) 0.3245(2) 0.0438(10) Uani 1 1 d .
C37 C 0.8873(5) 0.10301(10) 0.3936(2) 0.0433(10) Uani 1 1 d .
H37 H 0.9555 0.0835 0.4101 0.052 Uiso 1 1 calc R
C38 C 0.8755(4) 0.13472(10) 0.4385(2) 0.0389(9) Uani 1 1 d .
H38 H 0.9354 0.1366 0.4847 0.047 Uiso 1 1 calc R
C39 C 0.7734(4) 0.16391(9) 0.41453(19) 0.0319(8) Uani 1 1 d .
C40 C 0.6862(4) 0.16089(10) 0.3462(2) 0.0398(9) Uani 1 1 d .
H40 H 0.6177 0.1804 0.3300 0.048 Uiso 1 1 calc R
C41 C 0.7000(5) 0.12869(11) 0.3013(2) 0.0482(10) Uani 1 1 d .
H41 H 0.6407 0.1269 0.2550 0.058 Uiso 1 1 calc R
C42 C 0.8974(9) 0.02144(15) 0.0829(3) 0.133(3) Uani 1 1 d .
H42A H 0.8200 0.0136 0.1179 0.199 Uiso 1 1 calc R
H42B H 0.9996 0.0242 0.1098 0.199 Uiso 1 1 calc R
H42C H 0.9042 0.0027 0.0434 0.199 Uiso 1 1 calc R
C43 C 0.8469(7) 0.05947(14) 0.0470(3) 0.0796(16) Uani 1 1 d .
C44 C 0.7464(7) 0.06128(13) -0.0178(3) 0.0788(16) Uani 1 1 d .
H44 H 0.7098 0.0389 -0.0409 0.095 Uiso 1 1 calc R
C45 C 0.6988(6) 0.09600(11) -0.0492(2) 0.0592(12) Uani 1 1 d .
H45 H 0.6327 0.0968 -0.0937 0.071 Uiso 1 1 calc R
C46 C 0.7498(5) 0.12937(10) -0.0143(2) 0.0405(9) Uani 1 1 d .
C47 C 0.8502(5) 0.12783(12) 0.0503(2) 0.0632(13) Uani 1 1 d .
H47 H 0.8855 0.1501 0.0743 0.076 Uiso 1 1 calc R
C48 C 0.8989(6) 0.09276(15) 0.0798(3) 0.0801(16) Uani 1 1 d .
H48 H 0.9686 0.0920 0.1230 0.096 Uiso 1 1 calc R
N1 N 0.2038(3) 0.22351(8) 0.55499(15) 0.0328(7) Uani 1 1 d .
H1A H 0.1717 0.2007 0.5714 0.039 Uiso 1 1 calc R
H1B H 0.1183 0.2353 0.5325 0.039 Uiso 1 1 calc R
N2 N 0.0438(3) 0.22959(7) 0.70472(14) 0.0286(7) Uani 1 1 d .
N3 N -0.1803(3) 0.16722(7) 0.68657(15) 0.0288(7) Uani 1 1 d .
H3A H -0.0770 0.1628 0.7004 0.035 Uiso 1 1 calc R
H3B H -0.1896 0.1688 0.6353 0.035 Uiso 1 1 calc R
N4 N 0.2897(3) 0.20174(7) 0.88529(15) 0.0339(7) Uani 1 1 d .
H4A H 0.3936 0.1959 0.8932 0.041 Uiso 1 1 calc R
H4B H 0.2679 0.2207 0.9175 0.041 Uiso 1 1 calc R
O1 O 0.1219(3) 0.14300(7) 0.59041(13) 0.0463(7) Uani 1 1 d .
O2 O 0.3587(3) 0.16045(6) 0.66577(13) 0.0365(6) Uani 1 1 d .
O3 O 0.1274(3) 0.13695(6) 0.72787(12) 0.0326(6) Uani 1 1 d .
O4 O 0.6393(3) 0.22893(6) 0.43504(12) 0.0363(6) Uani 1 1 d .
O5 O 0.9136(3) 0.22235(7) 0.47766(15) 0.0502(7) Uani 1 1 d .
O6 O 0.7096(3) 0.19088(6) 0.54609(12) 0.0400(6) Uani 1 1 d .
O7 O 0.5821(3) 0.16594(7) -0.11842(13) 0.0419(6) Uani 1 1 d .
O8 O 0.8401(3) 0.19083(7) -0.07738(15) 0.0523(7) Uani 1 1 d .
O9 O 0.6211(3) 0.19520(7) 0.00576(13) 0.0432(7) Uani 1 1 d .
F1 F 0.4027(3) 0.14013(6) 0.48269(13) 0.0562(6) Uani 1 1 d .
F2 F 0.3054(3) 0.09665(6) 0.36395(15) 0.0750(8) Uani 1 1 d .
F3 F 0.1237(3) 0.12675(7) 0.24582(14) 0.0717(8) Uani 1 1 d .
F4 F 0.0382(3) 0.20114(7) 0.24950(12) 0.0633(7) Uani 1 1 d .
F5 F 0.1352(2) 0.24451(5) 0.36801(11) 0.0457(5) Uani 1 1 d .
F6 F -0.0856(3) 0.08431(7) 0.80378(13) 0.0612(7) Uani 1 1 d .
F7 F 0.0294(3) 0.01861(7) 0.75326(16) 0.0871(9) Uani 1 1 d .
F8 F -0.0412(4) -0.00366(7) 0.60680(17) 0.0929(9) Uani 1 1 d .
F9 F -0.2300(4) 0.04015(7) 0.51292(15) 0.0862(9) Uani 1 1 d .
F10 F -0.3445(3) 0.10619(6) 0.56424(12) 0.0572(6) Uani 1 1 d .
F11 F 0.2593(3) 0.20100(6) 1.05034(11) 0.0491(6) Uani 1 1 d .
F12 F 0.3805(3) 0.16235(6) 1.17262(12) 0.0623(7) Uani 1 1 d .
F13 F 0.4284(3) 0.08654(7) 1.16340(14) 0.0816(8) Uani 1 1 d .
F14 F 0.3640(4) 0.04997(7) 1.02879(15) 0.0882(9) Uani 1 1 d .
F15 F 0.2591(3) 0.08896(6) 0.90476(13) 0.0697(7) Uani 1 1 d .
S1 S 0.22052(11) 0.13581(3) 0.65970(5) 0.0329(2) Uani 1 1 d .
S2 S 0.75806(10) 0.20450(2) 0.47301(5) 0.0309(2) Uani 1 1 d .
S3 S 0.69424(11) 0.17401(3) -0.05398(5) 0.0361(2) Uani 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'
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'
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'
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
F1 C1 C2 118.6(4) . .
F1 C1 C6 119.3(3) . .
C2 C1 C6 122.1(4) . .
F3 C3 C2 120.2(4) . .
F3 C3 C4 120.0(4) . .
C2 C3 C4 119.7(4) . .
F2 C2 C3 120.3(4) . .
F2 C2 C1 119.5(4) . .
C3 C2 C1 120.2(4) . .
F4 C4 C5 120.6(3) . .
F4 C4 C3 120.2(3) . .
C5 C4 C3 119.2(4) . .
F5 C5 C4 117.3(3) . .
F5 C5 C6 119.3(3) . .
C4 C5 C6 123.4(3) . .
C5 C6 C1 115.3(3) . .
C5 C6 C7 123.1(3) . .
C1 C6 C7 121.4(3) . .
N1 C7 C6 112.9(3) . .
N1 C7 H7A 109.0 . .
C6 C7 H7A 109.0 . .
N1 C7 H7B 109.0 . .
C6 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
N1 C8 C9 111.2(3) . .
N1 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
N1 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
N2 C9 C8 114.3(3) . .
N2 C9 H9A 108.7 . .
C8 C9 H9A 108.7 . .
N2 C9 H9B 108.7 . .
C8 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
N2 C10 C11 114.0(3) . .
N2 C10 H10A 108.8 . .
C11 C10 H10A 108.8 . .
N2 C10 H10B 108.8 . .
C11 C10 H10B 108.8 . .
H10A C10 H10B 107.7 . .
N3 C11 C10 111.0(3) . .
N3 C11 H11A 109.4 . .
C10 C11 H11A 109.4 . .
N3 C11 H11B 109.4 . .
C10 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
N3 C12 C13 111.1(3) . .
N3 C12 H12A 109.4 . .
C13 C12 H12A 109.4 . .
N3 C12 H12B 109.4 . .
C13 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C18 C13 C14 115.6(3) . .
C18 C13 C12 121.7(3) . .
C14 C13 C12 122.7(3) . .
F6 C14 C15 118.5(4) . .
F6 C14 C13 119.1(3) . .
C15 C14 C13 122.4(4) . .
F7 C15 C16 120.9(4) . .
F7 C15 C14 119.7(4) . .
C16 C15 C14 119.4(4) . .
C15 C16 F8 120.0(4) . .
C15 C16 C17 120.4(4) . .
F8 C16 C17 119.6(4) . .
F9 C17 C16 120.3(4) . .
F9 C17 C18 120.1(4) . .
C16 C17 C18 119.6(4) . .
F10 C18 C17 119.0(4) . .
F10 C18 C13 118.4(3) . .
C17 C18 C13 122.6(4) . .
N2 C19 C20 113.7(3) . .
N2 C19 H19A 108.8 . .
C20 C19 H19A 108.8 . .
N2 C19 H19B 108.8 . .
C20 C19 H19B 108.8 . .
H19A C19 H19B 107.7 . .
N4 C20 C19 111.6(3) . .
N4 C20 H20A 109.3 . .
C19 C20 H20A 109.3 . .
N4 C20 H20B 109.3 . .
C19 C20 H20B 109.3 . .
H20A C20 H20B 108.0 . .
N4 C21 C22 113.1(3) . .
N4 C21 H21A 109.0 . .
C22 C21 H21A 109.0 . .
N4 C21 H21B 109.0 . .
C22 C21 H21B 109.0 . .
H21A C21 H21B 107.8 . .
C23 C22 C27 115.5(3) . .
C23 C22 C21 123.1(3) . .
C27 C22 C21 121.4(3) . .
F11 C23 C24 118.2(3) 1 .
F11 C23 C24 118.2(3) . .
F11 C23 C22 118.7(3) 1 .
F11 C23 C22 118.7(3) . .
C24 C23 C22 123.1(3) . .
F12 C24 C25 119.9(3) . .
F12 C24 C23 120.6(3) . .
C25 C24 C23 119.4(3) . .
F13 C25 C26 120.7(4) . .
F13 C25 C24 119.9(4) . .
C26 C25 C24 119.4(4) . .
F14 C26 C25 119.4(4) . .
F14 C26 C27 120.6(4) . .
C25 C26 C27 119.9(4) . .
F15 C27 C26 117.5(4) . .
F15 C27 C22 119.9(3) . .
C26 C27 C22 122.6(4) . .
C29 C28 H28A 109.5 . .
C29 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C29 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C34 C29 C30 117.8(5) . .
C34 C29 C28 121.6(6) . .
C30 C29 C28 120.6(6) . .
C29 C30 C31 120.9(5) . .
C29 C30 H30 119.6 . .
C31 C30 H30 119.6 . .
C32 C31 C30 120.1(4) . .
C32 C31 H31 120.0 . .
C30 C31 H31 120.0 . .
C31 C32 C33 119.8(4) . .
C31 C32 S1 119.1(3) . 1
C33 C32 S1 121.0(3) . 1
C31 C32 S1 119.1(3) . .
C33 C32 S1 121.0(3) . .
C32 C33 C34 118.9(5) . .
C32 C33 H33 120.6 . .
C34 C33 H33 120.6 . .
C29 C34 C33 122.6(5) . .
C29 C34 H34 118.7 . .
C33 C34 H34 118.7 . .
C36 C35 H35A 109.5 . .
C36 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
C36 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C37 C36 C41 117.9(3) . .
C37 C36 C35 120.4(4) . .
C41 C36 C35 121.7(4) . .
C38 C37 C36 121.9(4) . .
C38 C37 H37 119.1 . .
C36 C37 H37 119.1 . .
C37 C38 C39 119.5(4) . .
C37 C38 H38 120.3 . .
C39 C38 H38 120.3 . .
C40 C39 C38 119.8(3) . .
C40 C39 S2 121.0(3) . .
C38 C39 S2 119.2(3) . .
C39 C40 C41 120.0(3) . .
C39 C40 H40 120.0 . .
C41 C40 H40 120.0 . .
C36 C41 C40 120.9(4) . .
C36 C41 H41 119.5 . .
C40 C41 H41 119.5 . .
C43 C42 H42A 109.5 . .
C43 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C43 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C48 C43 C44 118.2(4) . .
C48 C43 C42 120.3(5) . .
C44 C43 C42 121.4(5) . .
C43 C44 C45 121.1(5) . .
C43 C44 H44 119.5 . .
C45 C44 H44 119.5 . .
C46 C45 C44 119.9(4) . .
C46 C45 H45 120.1 . .
C44 C45 H45 120.1 . .
C47 C46 C45 119.4(4) . .
C47 C46 S3 119.6(3) . .
C45 C46 S3 120.9(3) . .
C46 C47 C48 119.6(4) . .
C46 C47 H47 120.2 . .
C48 C47 H47 120.2 . .
C43 C48 C47 121.7(5) . .
C43 C48 H48 119.1 . .
C47 C48 H48 119.1 . .
C7 N1 C8 111.9(3) . .
C7 N1 H1A 109.2 . .
C8 N1 H1A 109.2 . .
C7 N1 H1B 109.2 . .
C8 N1 H1B 109.2 . .
H1A N1 H1B 107.9 . .
C19 N2 C10 109.2(2) . .
C19 N2 C9 112.7(3) . .
C10 N2 C9 110.4(3) . .
C11 N3 C12 111.8(2) . .
C11 N3 H3A 109.3 . .
C12 N3 H3A 109.3 . .
C11 N3 H3B 109.3 . .
C12 N3 H3B 109.3 . .
H3A N3 H3B 107.9 . .
C21 N4 C20 114.0(3) . .
C21 N4 H4A 108.8 . .
C20 N4 H4A 108.8 . .
C21 N4 H4B 108.8 . .
C20 N4 H4B 108.8 . .
H4A N4 H4B 107.6 . .
O2 S1 O1 111.90(15) 1 1
O2 S1 O1 111.90(15) . 1
O2 S1 O1 111.90(15) 1 .
O2 S1 O1 111.90(15) . .
O2 S1 O3 112.75(14) 1 .
O2 S1 O3 112.75(14) . .
O1 S1 O3 111.81(14) 1 .
O1 S1 O3 111.81(14) . .
O2 S1 O3 112.75(14) 1 1
O2 S1 O3 112.75(14) . 1
O1 S1 O3 111.81(14) 1 1
O1 S1 O3 111.81(14) . 1
O2 S1 C32 105.50(15) 1 .
O2 S1 C32 105.50(15) . .
O1 S1 C32 108.73(17) 1 .
O1 S1 C32 108.73(17) . .
O3 S1 C32 105.67(16) . .
O3 S1 C32 105.67(16) 1 .
O6 S2 O5 113.14(16) . .
O6 S2 O4 112.42(14) . .
O5 S2 O4 111.26(15) . .
O6 S2 C39 106.18(15) . .
O5 S2 C39 106.74(15) . .
O4 S2 C39 106.57(15) . .
O8 S3 O9 113.32(16) . .
O8 S3 O7 112.46(16) . .
O9 S3 O7 112.24(15) . .
O8 S3 C46 105.51(17) . .
O9 S3 C46 106.65(16) . .
O7 S3 C46 105.97(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.337(4) .
C1 C2 1.369(5) .
C1 C6 1.388(5) .
C3 F3 1.346(4) .
C3 C2 1.357(5) .
C3 C4 1.367(5) .
C2 F2 1.349(4) .
C4 F4 1.346(4) .
C4 C5 1.364(5) .
C5 F5 1.347(4) .
C5 C6 1.377(5) .
C6 C7 1.507(5) .
C7 N1 1.491(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N1 1.495(4) .
C8 C9 1.510(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N2 1.471(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N2 1.471(4) .
C10 C11 1.510(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 N3 1.488(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 N3 1.492(4) .
C12 C13 1.498(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C18 1.378(5) .
C13 C14 1.379(5) .
C14 F6 1.340(4) .
C14 C15 1.372(5) .
C15 F7 1.343(4) .
C15 C16 1.352(6) .
C16 F8 1.348(4) .
C16 C17 1.354(6) .
C17 F9 1.349(4) .
C17 C18 1.363(5) .
C18 F10 1.343(4) .
C19 N2 1.472(4) .
C19 C20 1.517(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 N4 1.501(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 N4 1.492(4) .
C21 C22 1.502(5) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.374(5) .
C22 C27 1.378(5) .
C23 F11 1.349(4) 1
C23 F11 1.349(4) .
C23 C24 1.366(5) .
C24 F12 1.342(4) .
C24 C25 1.367(5) .
C25 F13 1.343(4) .
C25 C26 1.364(5) .
C26 F14 1.351(4) .
C26 C27 1.366(5) .
C27 F15 1.347(4) .
C28 C29 1.523(6) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 C34 1.361(7) .
C29 C30 1.378(7) .
C30 C31 1.397(5) .
C30 H30 0.9300 .
C31 C32 1.365(5) .
C31 H31 0.9300 .
C32 C33 1.382(5) .
C32 S1 1.764(4) 1
C32 S1 1.764(4) .
C33 C34 1.387(6) .
C33 H33 0.9300 .
C34 H34 0.9300 .
C35 C36 1.509(5) .
C35 H35A 0.9600 .
C35 H35B 0.9600 .
C35 H35C 0.9600 .
C36 C37 1.381(5) .
C36 C41 1.384(5) .
C37 C38 1.374(5) .
C37 H37 0.9300 .
C38 C39 1.388(5) .
C38 H38 0.9300 .
C39 C40 1.371(5) .
C39 S2 1.768(3) .
C40 C41 1.389(5) .
C40 H40 0.9300 .
C41 H41 0.9300 .
C42 C43 1.529(6) .
C42 H42A 0.9600 .
C42 H42B 0.9600 .
C42 H42C 0.9600 .
C43 C48 1.366(6) .
C43 C44 1.376(6) .
C44 C45 1.391(6) .
C44 H44 0.9300 .
C45 C46 1.381(5) .
C45 H45 0.9300 .
C46 C47 1.374(5) .
C46 S3 1.770(4) .
C47 C48 1.391(6) .
C47 H47 0.9300 .
C48 H48 0.9300 .
N1 H1A 0.9000 .
N1 H1B 0.9000 .
N3 H3A 0.9000 .
N3 H3B 0.9000 .
N4 H4A 0.9000 .
N4 H4B 0.9000 .
O1 O1 0.000(7) 1
O1 S1 1.452(2) .
O1 S1 1.452(2) 1
O2 S1 1.448(2) .
O2 S1 1.448(2) 1
O3 S1 1.465(2) .
O3 S1 1.465(2) 1
O4 S2 1.449(2) .
O5 S2 1.447(2) .
O6 S2 1.448(2) .
O7 S3 1.456(2) .
O8 S3 1.442(2) .
O9 S3 1.450(2) .
S1 O2 1.448(2) 1
S1 O1 1.452(2) 1
S1 O3 1.465(2) 1
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
N4 H4B F11 0.90 2.43 2.918(3) 114.0 1
N3 H3A S1 0.90 2.80 3.599(3) 148.0 1
N3 H3A O3 0.90 1.98 2.849(3) 162.5 1
N1 H1A S1 0.90 2.78 3.591(3) 151.2 1
N1 H1A O2 0.90 2.63 3.178(4) 120.3 1
N1 H1A O1 0.90 2.10 2.991(4) 168.0 1
N3 H3B O6 0.90 1.90 2.710(3) 149.0 1_455
N1 H1B O5 0.90 1.97 2.719(4) 139.1 1_455
N1 H1B O9 0.90 2.49 3.058(4) 121.4 4_566
N4 H4B S2 0.90 2.81 3.658(3) 157.4 4_566
N4 H4B O5 0.90 2.55 3.264(4) 137.2 4_566
N4 H4B O4 0.90 2.11 2.905(4) 147.1 4_566
N4 H4A S3 0.90 2.75 3.634(3) 168.6 1_556
N4 H4A O7 0.90 1.92 2.764(4) 155.0 1_556
