#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:28:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178813 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/67/4106714.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_4106714
loop_
_publ_author_name
'Nathalie Busschaert'
'Marco Wenzel'
'Mark E. Light'
'Paulina Iglesias-Hernández'
'Ricardo Pérez-Tomás'
'Philip A. Gale'
_publ_contact_author_email       philip.gale@soton.ac.uk
_publ_contact_author_name        'Gale, Philip'
_publ_section_title
;
 Structure-Activity Relationships in Tripodal Transmembrane Anion
 Transporters: The Effect of Fluorination
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14136
_journal_page_last               14148
_journal_paper_doi               10.1021/ja205884y
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety
'2(C27 H30 F3 N7 S3), 2(C16 H36 N), 2(C4 H10 O), O4 S'
_chemical_formula_sum            'C94 H152 F6 N16 O6 S7'
_chemical_formula_weight         1940.81
_chemical_name_systematic
;
 ?
;
_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                110.7390(10)
_cell_angle_beta                 108.8380(10)
_cell_angle_gamma                97.0670(10)
_cell_formula_units_Z            1
_cell_length_a                   13.3402(2)
_cell_length_b                   13.9433(3)
_cell_length_c                   16.0351(3)
_cell_measurement_reflns_used    11515
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     2543.25(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            57930
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.0272(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         11670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+1.9389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                9120
_reflns_number_total             11670
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja205884y_si_001_08.cif
_cod_data_source_block           2011nb0004a
_cod_database_code               4106714
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C50 C 1.0156(4) 0.1018(6) 0.6506(7) 0.140(3) Uani 1 1 d .
H50A H 0.9399 0.0610 0.6096 0.168 Uiso 1 1 calc R
H50B H 1.0401 0.0822 0.7047 0.168 Uiso 1 1 calc R
C51 C 0.9567(3) 0.2226(3) 0.7329(3) 0.0691(10) Uani 1 1 d .
H51A H 0.9787 0.2046 0.7881 0.083 Uiso 1 1 calc R
H51B H 0.8800 0.1846 0.6930 0.083 Uiso 1 1 calc R
C52 C 0.9669(2) 0.3422(2) 0.7703(2) 0.0409(6) Uani 1 1 d .
H52A H 0.9234 0.3600 0.8082 0.061 Uiso 1 1 calc R
H52B H 0.9410 0.3606 0.7163 0.061 Uiso 1 1 calc R
H52C H 1.0424 0.3810 0.8099 0.061 Uiso 1 1 calc R
C53 C 1.0918(6) 0.0742(6) 0.5890(6) 0.137(3) Uani 1 1 d .
H53A H 1.0817 -0.0014 0.5605 0.206 Uiso 1 1 calc R
H53B H 1.1677 0.1089 0.6313 0.206 Uiso 1 1 calc R
H53C H 1.0712 0.0987 0.5385 0.206 Uiso 1 1 calc R
O1 O 0.5773(2) 1.1069(2) 0.0606(2) 0.0246(6) Uani 0.50 1 d P
O3 O 0.4244(3) 0.9816(3) 0.0482(2) 0.0277(7) Uani 0.50 1 d P
O2 O 0.5673(3) 1.0053(2) 0.0956(2) 0.0257(6) Uani 0.50 1 d P
O4 O 0.4412(3) 1.0820(2) 0.0113(2) 0.0272(7) Uani 0.50 1 d P
O10 O 1.0206(2) 0.1856(4) 0.6774(2) 0.1003(12) Uani 1 1 d .
S1 S 0.5000 1.0000 0.0000 0.01849(16) Uani 1 2 d S
C1 C 0.83895(19) 0.79956(19) 0.01109(18) 0.0300(5) Uani 1 1 d .
H1A H 0.8764 0.7535 -0.0212 0.036 Uiso 1 1 calc R
H1B H 0.8805 0.8271 0.0805 0.036 Uiso 1 1 calc R
C2 C 0.83587(19) 0.89164(18) -0.01845(17) 0.0295(5) Uani 1 1 d .
H2A H 0.9092 0.9244 -0.0096 0.035 Uiso 1 1 calc R
H2B H 0.7886 0.8651 -0.0866 0.035 Uiso 1 1 calc R
C3 C 0.85615(18) 1.04302(18) 0.13025(17) 0.0262(5) Uani 1 1 d .
C4 C 0.84139(18) 1.17962(18) 0.27183(17) 0.0266(5) Uani 1 1 d .
C5 C 0.8317(2) 1.28103(19) 0.28613(18) 0.0331(5) Uani 1 1 d .
H5 H 0.8010 1.2964 0.2330 0.040 Uiso 1 1 calc R
C6 C 0.8676(2) 1.3605(2) 0.37967(19) 0.0363(6) Uani 1 1 d .
H6 H 0.8606 1.4288 0.3899 0.044 Uiso 1 1 calc R
C7 C 0.91330(19) 1.33573(19) 0.45617(17) 0.0307(5) Uani 1 1 d .
C8 C 0.92490(19) 1.23534(19) 0.44489(18) 0.0306(5) Uani 1 1 d .
H8 H 0.9565 1.2210 0.4985 0.037 Uiso 1 1 calc R
C9 C 0.88808(19) 1.15656(19) 0.35128(17) 0.0292(5) Uani 1 1 d .
H9 H 0.8946 1.0882 0.3415 0.035 Uiso 1 1 calc R
C10 C 0.7230(2) 0.69824(19) 0.05896(17) 0.0301(5) Uani 1 1 d .
H10A H 0.7913 0.6812 0.0855 0.036 Uiso 1 1 calc R
H10B H 0.6636 0.6336 0.0284 0.036 Uiso 1 1 calc R
C11 C 0.7048(2) 0.7814(2) 0.14096(17) 0.0319(5) Uani 1 1 d .
H11A H 0.7133 0.7582 0.1926 0.038 Uiso 1 1 calc R
H11B H 0.7603 0.8481 0.1672 0.038 Uiso 1 1 calc R
C12 C 0.5041(2) 0.73523(18) 0.09764(16) 0.0263(5) Uani 1 1 d .
C13 C 0.29856(19) 0.71533(17) 0.02729(15) 0.0246(4) Uani 1 1 d .
C14 C 0.2542(2) 0.63086(19) 0.04306(18) 0.0321(5) Uani 1 1 d .
H14 H 0.3006 0.6011 0.0775 0.038 Uiso 1 1 calc R
C15 C 0.1413(2) 0.5910(2) 0.0076(2) 0.0368(6) Uani 1 1 d .
H15 H 0.1117 0.5348 0.0185 0.044 Uiso 1 1 calc R
C16 C 0.0731(2) 0.6351(2) -0.04377(19) 0.0330(5) Uani 1 1 d .
C17 C 0.1132(2) 0.71970(19) -0.05947(18) 0.0325(5) Uani 1 1 d .
H17 H 0.0659 0.7496 -0.0930 0.039 Uiso 1 1 calc R
C18 C 0.2265(2) 0.75931(18) -0.02376(16) 0.0279(5) Uani 1 1 d .
H18 H 0.2552 0.8164 -0.0340 0.033 Uiso 1 1 calc R
C19 C 0.68203(19) 0.65174(18) -0.11232(17) 0.0287(5) Uani 1 1 d .
H19A H 0.7070 0.5897 -0.1106 0.034 Uiso 1 1 calc R
H19B H 0.7088 0.6749 -0.1534 0.034 Uiso 1 1 calc R
C20 C 0.5567(2) 0.62136(18) -0.15542(17) 0.0302(5) Uani 1 1 d .
H20A H 0.5294 0.5585 -0.2164 0.036 Uiso 1 1 calc R
H20B H 0.5302 0.6039 -0.1115 0.036 Uiso 1 1 calc R
C21 C 0.48567(17) 0.71770(17) -0.25654(15) 0.0227(4) Uani 1 1 d .
C22 C 0.41214(18) 0.84585(18) -0.32221(16) 0.0259(5) Uani 1 1 d .
C23 C 0.35046(19) 0.78068(19) -0.41963(16) 0.0284(5) Uani 1 1 d .
H23 H 0.3395 0.7073 -0.4424 0.034 Uiso 1 1 calc R
C24 C 0.3048(2) 0.8255(2) -0.48342(18) 0.0336(5) Uani 1 1 d .
H24 H 0.2639 0.7826 -0.5490 0.040 Uiso 1 1 calc R
C25 C 0.3210(2) 0.9334(2) -0.4482(2) 0.0387(6) Uani 1 1 d .
C26 C 0.3806(3) 0.9995(2) -0.3532(2) 0.0496(8) Uani 1 1 d .
H26 H 0.3900 1.0726 -0.3313 0.060 Uiso 1 1 calc R
C27 C 0.4272(2) 0.9558(2) -0.2897(2) 0.0437(7) Uani 1 1 d .
H27 H 0.4689 1.0002 -0.2246 0.052 Uiso 1 1 calc R
C28 C 0.41901(17) 0.31388(17) 0.54174(15) 0.0216(4) Uani 1 1 d .
H28A H 0.4456 0.3874 0.5894 0.026 Uiso 1 1 calc R
H28B H 0.4519 0.3080 0.4949 0.026 Uiso 1 1 calc R
C29 C 0.45923(18) 0.24414(18) 0.59293(16) 0.0261(5) Uani 1 1 d .
H29A H 0.4477 0.1731 0.5453 0.031 Uiso 1 1 calc R
H29B H 0.4179 0.2389 0.6318 0.031 Uiso 1 1 calc R
C30 C 0.58155(19) 0.29249(19) 0.65809(17) 0.0281(5) Uani 1 1 d .
H30A H 0.6205 0.3091 0.6211 0.034 Uiso 1 1 calc R
H30B H 0.5910 0.3585 0.7116 0.034 Uiso 1 1 calc R
C31 C 0.6311(2) 0.2176(2) 0.69827(19) 0.0358(6) Uani 1 1 d .
H31A H 0.7078 0.2506 0.7384 0.054 Uiso 1 1 calc R
H31B H 0.6228 0.1525 0.6455 0.054 Uiso 1 1 calc R
H31C H 0.5939 0.2023 0.7362 0.054 Uiso 1 1 calc R
C32 C 0.24713(18) 0.17264(16) 0.41635(15) 0.0238(4) Uani 1 1 d .
H32A H 0.1676 0.1575 0.3914 0.029 Uiso 1 1 calc R
H32B H 0.2680 0.1283 0.4504 0.029 Uiso 1 1 calc R
C33 C 0.28099(19) 0.13976(17) 0.33044(16) 0.0265(5) Uani 1 1 d .
H33A H 0.3588 0.1717 0.3521 0.032 Uiso 1 1 calc R
H33B H 0.2403 0.1638 0.2832 0.032 Uiso 1 1 calc R
C34 C 0.2565(2) 0.01869(19) 0.28470(17) 0.0352(6) Uani 1 1 d .
H34A H 0.3086 -0.0028 0.3279 0.042 Uiso 1 1 calc R
H34B H 0.1835 -0.0117 0.2783 0.042 Uiso 1 1 calc R
C35 C 0.2624(3) -0.0262(2) 0.1863(2) 0.0460(7) Uani 1 1 d .
H35A H 0.2460 -0.1024 0.1616 0.069 Uiso 1 1 calc R
H35B H 0.3350 0.0019 0.1922 0.069 Uiso 1 1 calc R
H35C H 0.2100 -0.0067 0.1425 0.069 Uiso 1 1 calc R
C36 C 0.27572(17) 0.36278(17) 0.43881(15) 0.0215(4) Uani 1 1 d .
H36A H 0.3088 0.3464 0.3915 0.026 Uiso 1 1 calc R
H36B H 0.3137 0.4353 0.4867 0.026 Uiso 1 1 calc R
C37 C 0.15560(18) 0.35779(18) 0.38737(16) 0.0260(5) Uani 1 1 d .
H37A H 0.1313 0.4046 0.4333 0.031 Uiso 1 1 calc R
H37B H 0.1103 0.2858 0.3621 0.031 Uiso 1 1 calc R
C38 C 0.1421(2) 0.3914(2) 0.30400(18) 0.0335(5) Uani 1 1 d .
H38A H 0.1542 0.3369 0.2533 0.040 Uiso 1 1 calc R
H38B H 0.0669 0.3946 0.2770 0.040 Uiso 1 1 calc R
C39 C 0.2187(2) 0.4975(2) 0.3323(2) 0.0405(6) Uani 1 1 d .
H39A H 0.2052 0.5124 0.2762 0.061 Uiso 1 1 calc R
H39B H 0.2935 0.4947 0.3575 0.061 Uiso 1 1 calc R
H39C H 0.2059 0.5525 0.3810 0.061 Uiso 1 1 calc R
C40 C 0.23846(18) 0.30399(17) 0.55978(15) 0.0234(4) Uani 1 1 d .
H40A H 0.1622 0.2996 0.5255 0.028 Uiso 1 1 calc R
H40B H 0.2391 0.2452 0.5788 0.028 Uiso 1 1 calc R
C41 C 0.28702(19) 0.40714(18) 0.65123(15) 0.0254(5) Uani 1 1 d .
H41A H 0.2955 0.4670 0.6343 0.031 Uiso 1 1 calc R
H41B H 0.3590 0.4078 0.6922 0.031 Uiso 1 1 calc R
C42 C 0.2114(2) 0.4173(2) 0.70608(17) 0.0298(5) Uani 1 1 d .
H42A H 0.1427 0.4255 0.6677 0.036 Uiso 1 1 calc R
H42B H 0.1948 0.3524 0.7144 0.036 Uiso 1 1 calc R
C43 C 0.2620(2) 0.5115(2) 0.80520(18) 0.0349(5) Uani 1 1 d .
H43A H 0.2117 0.5146 0.8368 0.052 Uiso 1 1 calc R
H43B H 0.2772 0.5761 0.7973 0.052 Uiso 1 1 calc R
H43C H 0.3293 0.5031 0.8440 0.052 Uiso 1 1 calc R
N1 N 0.72769(15) 0.73701(15) -0.01395(13) 0.0252(4) Uani 1 1 d .
N2 N 0.79527(15) 0.97079(15) 0.03890(14) 0.0273(4) Uani 1 1 d .
H2 H 0.7282 0.9715 0.0128 0.033 Uiso 1 1 calc R
N3 N 0.79762(16) 1.09818(16) 0.17541(14) 0.0298(4) Uani 1 1 d .
H3 H 0.7280 1.0826 0.1429 0.036 Uiso 1 1 calc R
N4 N 0.59626(16) 0.79887(16) 0.10809(14) 0.0286(4) Uani 1 1 d .
H4 H 0.5905 0.8529 0.0945 0.034 Uiso 1 1 calc R
N5 N 0.41164(16) 0.76344(15) 0.05852(14) 0.0273(4) Uani 1 1 d .
H5A H 0.4246 0.8215 0.0515 0.033 Uiso 1 1 calc R
N6 N 0.51381(17) 0.70706(16) -0.17228(13) 0.0290(4) Uani 1 1 d .
H6A H 0.5059 0.7544 -0.1248 0.035 Uiso 1 1 calc R
N7 N 0.45597(17) 0.80922(16) -0.25044(13) 0.0302(4) Uani 1 1 d .
H7 H 0.4657 0.8520 -0.1928 0.036 Uiso 1 1 calc R
N8 N 0.29521(14) 0.28854(13) 0.48937(12) 0.0202(4) Uani 1 1 d .
F1 F 0.94840(13) 1.41329(12) 0.54831(11) 0.0443(4) Uani 1 1 d .
F2 F -0.03839(13) 0.59387(13) -0.07961(13) 0.0460(4) Uani 1 1 d .
F3 F 0.27535(16) 0.97615(15) -0.51128(13) 0.0566(5) Uani 1 1 d .
S2 S 0.49021(5) 0.62680(4) -0.35697(4) 0.02654(15) Uani 1 1 d .
S3 S 0.99353(5) 1.06523(5) 0.18347(5) 0.03455(16) Uani 1 1 d .
S4 S 0.50800(6) 0.63396(5) 0.13131(5) 0.03681(17) 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
O10 C50 C53 110.1(5) . .
O10 C51 C52 115.2(4) . .
S1 O1 O4 54.87(14) . .
S1 O1 O2 54.67(14) . .
O4 O1 O2 91.2(2) . .
S1 O1 O3 55.15(14) . 2_675
O4 O1 O3 90.3(2) . 2_675
O2 O1 O3 89.1(2) . 2_675
S1 O3 O4 53.22(14) . .
S1 O3 O1 53.65(14) . 2_675
O4 O3 O1 88.7(2) . 2_675
S1 O3 O2 53.31(14) . .
O4 O3 O2 88.0(2) . .
O1 O3 O2 87.54(19) 2_675 .
S1 O2 O4 54.71(14) . 2_675
S1 O2 O1 54.76(14) . .
O4 O2 O1 91.3(2) 2_675 .
S1 O2 O3 54.89(14) . .
O4 O2 O3 89.7(2) 2_675 .
O1 O2 O3 89.2(2) . .
S1 O4 O1 56.00(15) . .
S1 O4 O2 55.73(15) . 2_675
O1 O4 O2 92.5(2) . 2_675
S1 O4 O3 55.82(15) . .
O1 O4 O3 91.5(2) . .
O2 O4 O3 90.7(2) 2_675 .
C50 O10 C51 116.9(6) . .
O4 S1 O4 180.000(1) 2_675 .
O4 S1 O2 110.44(17) 2_675 2_675
O4 S1 O2 69.56(17) . 2_675
O4 S1 O2 69.56(17) 2_675 .
O4 S1 O2 110.44(17) . .
O2 S1 O2 180.0(2) 2_675 .
O4 S1 O1 69.12(17) 2_675 2_675
O4 S1 O1 110.88(17) . 2_675
O2 S1 O1 70.57(17) 2_675 2_675
O2 S1 O1 109.43(17) . 2_675
O4 S1 O1 110.88(17) 2_675 .
O4 S1 O1 69.12(17) . .
O2 S1 O1 109.43(17) 2_675 .
O2 S1 O1 70.57(17) . .
O1 S1 O1 180.000(1) 2_675 .
O4 S1 O3 70.96(18) 2_675 2_675
O4 S1 O3 109.04(18) . 2_675
O2 S1 O3 71.80(17) 2_675 2_675
O2 S1 O3 108.20(17) . 2_675
O1 S1 O3 108.80(17) 2_675 2_675
O1 S1 O3 71.20(17) . 2_675
O4 S1 O3 109.04(18) 2_675 .
O4 S1 O3 70.96(18) . .
O2 S1 O3 108.20(17) 2_675 .
O2 S1 O3 71.80(17) . .
O1 S1 O3 71.20(17) 2_675 .
O1 S1 O3 108.80(17) . .
O3 S1 O3 180.000(1) 2_675 .
N1 C1 C2 111.89(19) . .
N2 C2 C1 111.04(19) . .
N2 C3 N3 114.0(2) . .
N2 C3 S3 123.06(18) . .
N3 C3 S3 122.88(17) . .
C5 C4 C9 120.0(2) . .
C5 C4 N3 119.1(2) . .
C9 C4 N3 120.8(2) . .
C4 C5 C6 120.3(2) . .
C7 C6 C5 118.4(2) . .
C6 C7 F1 118.8(2) . .
C6 C7 C8 123.0(2) . .
F1 C7 C8 118.2(2) . .
C7 C8 C9 118.1(2) . .
C8 C9 C4 120.2(2) . .
N1 C10 C11 111.16(19) . .
N4 C11 C10 111.99(19) . .
N4 C12 N5 112.60(19) . .
N4 C12 S4 121.75(18) . .
N5 C12 S4 125.65(18) . .
C14 C13 C18 118.5(2) . .
C14 C13 N5 126.3(2) . .
C18 C13 N5 115.20(19) . .
C15 C14 C13 120.2(2) . .
C16 C15 C14 119.6(2) . .
F2 C16 C17 118.9(2) . .
F2 C16 C15 119.0(2) . .
C17 C16 C15 122.1(2) . .
C16 C17 C18 118.0(2) . .
C17 C18 C13 121.6(2) . .
N1 C19 C20 111.56(19) . .
N6 C20 C19 111.96(19) . .
N6 C21 N7 112.97(19) . .
N6 C21 S2 122.34(17) . .
N7 C21 S2 124.69(16) . .
C23 C22 C27 119.0(2) . .
C23 C22 N7 124.7(2) . .
C27 C22 N7 116.1(2) . .
C22 C23 C24 119.8(2) . .
C25 C24 C23 119.1(2) . .
C26 C25 C24 122.7(2) . .
C26 C25 F3 118.9(3) . .
C24 C25 F3 118.5(2) . .
C25 C26 C27 118.6(3) . .
C26 C27 C22 120.8(2) . .
N8 C28 C29 115.88(17) . .
C28 C29 C30 109.55(18) . .
C31 C30 C29 112.0(2) . .
N8 C32 C33 116.27(17) . .
C32 C33 C34 108.35(19) . .
C35 C34 C33 113.7(2) . .
N8 C36 C37 115.69(17) . .
C36 C37 C38 110.36(18) . .
C39 C38 C37 114.7(2) . .
C41 C40 N8 116.43(17) . .
C40 C41 C42 109.66(19) . .
C43 C42 C41 112.5(2) . .
C19 N1 C10 112.58(18) . .
C19 N1 C1 111.76(18) . .
C10 N1 C1 112.45(18) . .
C3 N2 C2 124.0(2) . .
C3 N3 C4 125.79(19) . .
C12 N4 C11 123.8(2) . .
C12 N5 C13 132.22(19) . .
C21 N6 C20 125.0(2) . .
C21 N7 C22 131.10(19) . .
C28 N8 C32 111.10(16) . .
C28 N8 C40 111.29(15) . .
C32 N8 C40 105.93(15) . .
C28 N8 C36 106.23(15) . .
C32 N8 C36 110.93(15) . .
C40 N8 C36 111.46(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C50 O10 1.078(7) .
C50 C53 1.624(10) .
C51 O10 1.434(5) .
C51 C52 1.530(5) .
O1 S1 1.476(3) .
O1 O4 1.664(4) .
O1 O2 1.705(4) .
O1 O3 1.735(4) 2_675
O3 S1 1.504(3) .
O3 O4 1.719(4) .
O3 O1 1.735(4) 2_675
O3 O2 1.747(4) .
O2 S1 1.475(3) .
O2 O4 1.672(4) 2_675
O4 S1 1.457(3) .
O4 O2 1.672(4) 2_675
S1 O4 1.457(3) 2_675
S1 O2 1.475(3) 2_675
S1 O1 1.476(3) 2_675
S1 O3 1.504(3) 2_675
C1 N1 1.474(3) .
C1 C2 1.518(3) .
C2 N2 1.452(3) .
C3 N2 1.344(3) .
C3 N3 1.358(3) .
C3 S3 1.687(2) .
C4 C5 1.380(3) .
C4 C9 1.393(3) .
C4 N3 1.425(3) .
C5 C6 1.391(4) .
C6 C7 1.365(4) .
C7 F1 1.367(3) .
C7 C8 1.381(3) .
C8 C9 1.387(3) .
C10 N1 1.466(3) .
C10 C11 1.526(3) .
C11 N4 1.456(3) .
C12 N4 1.349(3) .
C12 N5 1.365(3) .
C12 S4 1.682(2) .
C13 C14 1.392(3) .
C13 C18 1.401(3) .
C13 N5 1.415(3) .
C14 C15 1.386(4) .
C15 C16 1.377(4) .
C16 F2 1.369(3) .
C16 C17 1.373(3) .
C17 C18 1.389(3) .
C19 N1 1.465(3) .
C19 C20 1.525(3) .
C20 N6 1.458(3) .
C21 N6 1.348(3) .
C21 N7 1.362(3) .
C21 S2 1.685(2) .
C22 C23 1.387(3) .
C22 C27 1.397(3) .
C22 N7 1.408(3) .
C23 C24 1.398(3) .
C24 C25 1.366(4) .
C25 C26 1.358(4) .
C25 F3 1.367(3) .
C26 C27 1.385(4) .
C28 N8 1.519(3) .
C28 C29 1.522(3) .
C29 C30 1.529(3) .
C30 C31 1.521(3) .
C32 N8 1.521(3) .
C32 C33 1.522(3) .
C33 C34 1.525(3) .
C34 C35 1.510(4) .
C36 N8 1.524(3) .
C36 C37 1.527(3) .
C37 C38 1.532(3) .
C38 C39 1.514(4) .
C40 C41 1.517(3) .
C40 N8 1.521(3) .
C41 C42 1.527(3) .
C42 C43 1.522(3) .
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
N2 H2 O4 0.86 2.15 2.917(4) 148.2 2_675
N2 H2 O3 0.86 2.24 3.077(4) 164.2 2_675
N3 H3 O2 0.86 2.03 2.840(4) 155.9 .
N3 H3 O1 0.86 2.16 2.965(4) 155.7 .
N4 H4 O4 0.86 2.15 2.918(4) 149.1 2_675
N4 H4 O2 0.86 2.18 3.018(4) 164.5 .
N5 H5A O3 0.86 2.25 3.091(4) 165.1 .
N5 H5A O1 0.86 2.34 3.082(4) 144.6 2_675
N6 H6A O4 0.86 2.20 2.977(4) 149.8 2_675
N6 H6A O1 0.86 2.43 3.210(4) 151.9 2_675
N7 H7 O2 0.86 2.25 3.016(4) 149.1 2_675
N7 H7 O1 0.86 2.27 3.051(4) 150.9 2_675
N7 H7 O3 0.86 2.46 3.222(4) 147.5 2_675
N7 H7 O4 0.86 2.52 3.295(4) 150.4 2_675
