#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025322.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_4025322
loop_
_publ_author_name
'Alejandro Dorazco-González'
'Herbert Höpfl'
'Felipe Medrano'
'Anatoly K. Yatsimirsky'
_publ_section_title
;
 Recognition of Anions and Neutral Guests by Dicationic
 Pyridine-2,6-dicarboxamide Receptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2259
_journal_page_last               2273
_journal_paper_doi               10.1021/jo100037m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H19 N5 O2, 2(C F3 O3 S)'
_chemical_formula_sum            'C21 H19 F6 N5 O8 S2'
_chemical_formula_weight         647.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 106.889(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.202(4)
_cell_length_b                   8.1643(12)
_cell_length_c                   22.883(3)
_cell_measurement_reflns_used    5717
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.20
_cell_volume                     5041.6(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47350
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.9060
_exptl_absorpt_correction_T_min  0.8610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     773
_refine_ls_number_reflns         8890
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+7.6755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                8043
_reflns_number_total             8890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100037m_si_004.cif
_cod_data_source_block           glinicx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        5041.6(13)
_cod_database_code               4025322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.46348(8) 0.6996(3) 0.51627(10) 0.0144(5) Uani 1 1 d . . .
N2 N 0.38037(9) 0.7916(3) 0.42748(11) 0.0156(5) Uani 1 1 d D . .
H2' H 0.3817(12) 0.727(3) 0.4577(10) 0.023 Uiso 1 1 d D . .
N3 N 0.29535(9) 0.8543(3) 0.39736(11) 0.0137(5) Uani 1 1 d . . .
N4 N 0.45141(9) 0.5536(3) 0.61640(11) 0.0170(5) Uani 1 1 d D . .
H4' H 0.4317(10) 0.622(3) 0.5928(12) 0.026 Uiso 1 1 d D . .
N5 N 0.38833(9) 0.4591(3) 0.65459(11) 0.0149(5) Uani 1 1 d . . .
O1 O 0.42791(8) 0.9390(3) 0.38177(9) 0.0221(5) Uani 1 1 d . . .
O2 O 0.53261(8) 0.4722(3) 0.64477(10) 0.0242(5) Uani 1 1 d . . .
C1 C 0.50446(11) 0.6413(4) 0.55702(13) 0.0162(6) Uani 1 1 d . . .
C2 C 0.55184(11) 0.6636(4) 0.55188(14) 0.0190(7) Uani 1 1 d . . .
H2 H 0.5798 0.6183 0.5812 0.023 Uiso 1 1 calc R . .
C3 C 0.55738(11) 0.7536(4) 0.50295(14) 0.0202(7) Uani 1 1 d . . .
H3 H 0.5894 0.7711 0.4982 0.024 Uiso 1 1 calc R . .
C4 C 0.51596(11) 0.8174(4) 0.46122(14) 0.0190(7) Uani 1 1 d . . .
H4 H 0.5187 0.8815 0.4277 0.023 Uiso 1 1 calc R . .
C5 C 0.46983(11) 0.7847(4) 0.46975(13) 0.0153(6) Uani 1 1 d . . .
C6 C 0.42485(11) 0.8472(4) 0.42202(13) 0.0163(6) Uani 1 1 d . . .
C7 C 0.33608(11) 0.8116(4) 0.38109(13) 0.0153(6) Uani 1 1 d . . .
C8 C 0.25109(11) 0.8712(4) 0.35481(14) 0.0173(6) Uani 1 1 d . . .
H8 H 0.2226 0.8963 0.3673 0.021 Uiso 1 1 calc R . .
C9 C 0.24653(11) 0.8527(4) 0.29419(14) 0.0189(7) Uani 1 1 d . . .
H9 H 0.2153 0.8670 0.2646 0.023 Uiso 1 1 calc R . .
C10 C 0.28806(11) 0.8129(4) 0.27641(14) 0.0197(7) Uani 1 1 d . . .
H10 H 0.2856 0.8003 0.2344 0.024 Uiso 1 1 calc R . .
C11 C 0.33293(11) 0.7918(4) 0.32020(13) 0.0175(6) Uani 1 1 d . . .
H11 H 0.3616 0.7637 0.3085 0.021 Uiso 1 1 calc R . .
C12 C 0.49865(11) 0.5472(4) 0.61074(13) 0.0168(6) Uani 1 1 d . . .
C13 C 0.43713(10) 0.4926(4) 0.66505(13) 0.0144(6) Uani 1 1 d . . .
C14 C 0.37052(11) 0.4095(4) 0.70078(14) 0.0194(7) Uani 1 1 d . . .
H14 H 0.3361 0.3890 0.6928 0.023 Uiso 1 1 calc R . .
C15 C 0.40124(12) 0.3885(4) 0.75852(14) 0.0215(7) Uani 1 1 d . . .
H15 H 0.3885 0.3525 0.7905 0.026 Uiso 1 1 calc R . .
C16 C 0.45134(12) 0.4205(4) 0.76986(14) 0.0211(7) Uani 1 1 d . . .
H16 H 0.4732 0.4071 0.8099 0.025 Uiso 1 1 calc R . .
C17 C 0.46943(11) 0.4716(4) 0.72336(13) 0.0173(6) Uani 1 1 d . . .
H17 H 0.5038 0.4925 0.7310 0.021 Uiso 1 1 calc R . .
C18 C 0.29847(12) 0.8818(4) 0.46238(13) 0.0200(7) Uani 1 1 d . . .
H18A H 0.3054 0.7777 0.4846 0.030 Uiso 1 1 calc R . .
H18B H 0.2669 0.9262 0.4653 0.030 Uiso 1 1 calc R . .
H18C H 0.3251 0.9598 0.4803 0.030 Uiso 1 1 calc R . .
C19 C 0.35374(11) 0.4748(4) 0.59253(13) 0.0186(7) Uani 1 1 d . . .
H19A H 0.3213 0.4312 0.5920 0.028 Uiso 1 1 calc R . .
H19B H 0.3666 0.4132 0.5637 0.028 Uiso 1 1 calc R . .
H19C H 0.3504 0.5906 0.5807 0.028 Uiso 1 1 calc R . .
C20 C 0.22551(11) 0.6891(4) 0.55664(13) 0.0173(6) Uani 1 1 d . . .
F1 F 0.26559(6) 0.7795(2) 0.58224(8) 0.0245(4) Uani 1 1 d . . .
F2 F 0.23788(6) 0.5827(2) 0.51908(8) 0.0240(4) Uani 1 1 d . . .
F3 F 0.19133(7) 0.7898(2) 0.52237(8) 0.0269(4) Uani 1 1 d . . .
S1 S 0.20293(3) 0.58358(9) 0.61327(3) 0.01631(17) Uani 1 1 d . . .
O3 O 0.24464(8) 0.4837(3) 0.64481(10) 0.0252(5) Uani 1 1 d . . .
O4 O 0.16106(8) 0.4953(3) 0.57506(10) 0.0227(5) Uani 1 1 d . . .
O5 O 0.19073(8) 0.7135(3) 0.64846(10) 0.0271(5) Uani 1 1 d . . .
C21 C 0.38319(11) 0.9053(4) 0.69383(13) 0.0165(6) Uani 1 1 d . . .
F4 F 0.37654(7) 1.0162(2) 0.73319(8) 0.0281(4) Uani 1 1 d . . .
F5 F 0.34400(7) 0.8042(2) 0.68138(8) 0.0284(4) Uani 1 1 d . . .
F6 F 0.42253(6) 0.8160(2) 0.72215(8) 0.0254(4) Uani 1 1 d . . .
S2 S 0.38992(3) 0.99851(9) 0.62416(3) 0.01690(17) Uani 1 1 d . . .
O6 O 0.34515(8) 1.0923(3) 0.60164(10) 0.0242(5) Uani 1 1 d . . .
O7 O 0.43431(8) 1.0934(3) 0.64623(11) 0.0306(6) Uani 1 1 d . . .
O8 O 0.39345(8) 0.8587(3) 0.58730(9) 0.0249(5) Uani 1 1 d . . .
N31 N 0.02996(8) 0.2086(3) 0.98131(10) 0.0139(5) Uani 1 1 d . . .
N32 N 0.11133(9) 0.3207(3) 1.06822(11) 0.0159(5) Uani 1 1 d D . .
H32' H 0.1108(12) 0.253(3) 1.0392(10) 0.024 Uiso 1 1 d D . .
N33 N 0.19707(9) 0.3620(3) 1.09325(11) 0.0149(5) Uani 1 1 d . . .
N34 N 0.04375(9) 0.0593(3) 0.88175(11) 0.0156(5) Uani 1 1 d D . .
H34' H 0.0622(10) 0.132(3) 0.9044(12) 0.023 Uiso 1 1 d D . .
N35 N 0.10663(9) -0.0476(3) 0.84604(10) 0.0138(5) Uani 1 1 d . . .
O31 O 0.06099(8) 0.4609(3) 1.11266(9) 0.0210(5) Uani 1 1 d . . .
O32 O -0.03560(8) -0.0388(3) 0.85687(10) 0.0261(5) Uani 1 1 d . . .
C31 C -0.01019(11) 0.1456(4) 0.94076(13) 0.0165(6) Uani 1 1 d . . .
C32 C -0.05812(11) 0.1652(4) 0.94438(14) 0.0195(7) Uani 1 1 d . . .
H32 H -0.0855 0.1182 0.9146 0.023 Uiso 1 1 calc R . .
C33 C -0.06496(11) 0.2548(4) 0.99242(14) 0.0210(7) Uani 1 1 d . . .
H33 H -0.0973 0.2704 0.9963 0.025 Uiso 1 1 calc R . .
C34 C -0.02441(11) 0.3215(4) 1.03469(14) 0.0202(7) Uani 1 1 d . . .
H34 H -0.0282 0.3838 1.0681 0.024 Uiso 1 1 calc R . .
C35 C 0.02209(10) 0.2952(4) 1.02711(13) 0.0154(6) Uani 1 1 d . . .
C36 C 0.06588(11) 0.3676(4) 1.07417(13) 0.0168(6) Uani 1 1 d . . .
C37 C 0.15593(10) 0.3524(3) 1.11213(13) 0.0138(6) Uani 1 1 d . . .
C38 C 0.24195(11) 0.3925(4) 1.13411(14) 0.0177(6) Uani 1 1 d . . .
H38 H 0.2706 0.3966 1.1202 0.021 Uiso 1 1 calc R . .
C39 C 0.24682(11) 0.4172(4) 1.19418(14) 0.0194(7) Uani 1 1 d . . .
H39 H 0.2783 0.4419 1.2219 0.023 Uiso 1 1 calc R . .
C40 C 0.20497(11) 0.4059(4) 1.21467(14) 0.0207(7) Uani 1 1 d . . .
H40 H 0.2077 0.4207 1.2567 0.025 Uiso 1 1 calc R . .
C41 C 0.15996(11) 0.3731(4) 1.17371(13) 0.0182(7) Uani 1 1 d . . .
H41 H 0.1313 0.3644 1.1874 0.022 Uiso 1 1 calc R . .
C42 C -0.00311(11) 0.0457(4) 0.88871(14) 0.0181(7) Uani 1 1 d . . .
C43 C 0.05790(11) -0.0100(4) 0.83423(14) 0.0163(6) Uani 1 1 d . . .
C44 C 0.12466(11) -0.1082(4) 0.80141(13) 0.0175(6) Uani 1 1 d . . .
H44 H 0.1590 -0.1327 0.8105 0.021 Uiso 1 1 calc R . .
C45 C 0.09429(12) -0.1344(4) 0.74392(14) 0.0202(7) Uani 1 1 d . . .
H45 H 0.1072 -0.1767 0.7130 0.024 Uiso 1 1 calc R . .
C46 C 0.04433(12) -0.0986(4) 0.73113(14) 0.0214(7) Uani 1 1 d . . .
H46 H 0.0227 -0.1163 0.6912 0.026 Uiso 1 1 calc R . .
C47 C 0.02605(11) -0.0374(4) 0.77622(13) 0.0168(6) Uani 1 1 d . . .
H47 H -0.0083 -0.0139 0.7677 0.020 Uiso 1 1 calc R . .
C48 C 0.19500(11) 0.3337(4) 1.02873(13) 0.0189(7) Uani 1 1 d . . .
H48A H 0.1862 0.2192 1.0180 0.028 Uiso 1 1 calc R . .
H48B H 0.2275 0.3573 1.0231 0.028 Uiso 1 1 calc R . .
H48C H 0.1700 0.4058 1.0024 0.028 Uiso 1 1 calc R . .
C49 C 0.14153(11) -0.0245(4) 0.90746(13) 0.0180(6) Uani 1 1 d . . .
H49A H 0.1480 0.0926 0.9151 0.027 Uiso 1 1 calc R . .
H49B H 0.1727 -0.0813 0.9099 0.027 Uiso 1 1 calc R . .
H49C H 0.1271 -0.0696 0.9381 0.027 Uiso 1 1 calc R . .
C50 C 0.12446(11) 0.3868(4) 0.80395(13) 0.0178(6) Uani 1 1 d . . .
F31 F 0.08780(6) 0.2891(2) 0.77334(8) 0.0231(4) Uani 1 1 d . . .
F32 F 0.16512(7) 0.2954(2) 0.82375(8) 0.0283(4) Uani 1 1 d . . .
F33 F 0.13250(7) 0.4961(2) 0.76468(8) 0.0256(4) Uani 1 1 d . . .
S31 S 0.10916(3) 0.48720(9) 0.86793(3) 0.01401(17) Uani 1 1 d . . .
O33 O 0.10347(8) 0.3513(3) 0.90554(9) 0.0215(5) Uani 1 1 d . . .
O34 O 0.15213(8) 0.5872(3) 0.89458(9) 0.0203(5) Uani 1 1 d . . .
O35 O 0.06446(8) 0.5747(3) 0.83932(10) 0.0225(5) Uani 1 1 d . . .
C51 C 0.31133(11) 0.2067(4) 0.86247(13) 0.0186(7) Uani 1 1 d . . .
F34 F 0.27650(7) 0.2859(2) 0.81960(8) 0.0259(4) Uani 1 1 d . . .
F35 F 0.33486(6) 0.1074(2) 0.83373(8) 0.0241(4) Uani 1 1 d . . .
F36 F 0.34407(6) 0.3185(2) 0.89225(8) 0.0241(4) Uani 1 1 d . . .
S32 S 0.28489(3) 0.09392(9) 0.91437(3) 0.01556(17) Uani 1 1 d . . .
O36 O 0.26605(8) 0.2211(3) 0.94453(10) 0.0274(5) Uani 1 1 d . . .
O37 O 0.24836(8) -0.0084(3) 0.87354(10) 0.0224(5) Uani 1 1 d . . .
O38 O 0.32753(8) 0.0073(3) 0.95191(9) 0.0217(5) 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
_geom_angle_publ_flag
C5 N1 C1 117.0(2) . . ?
C6 N2 C7 122.1(2) . . ?
C8 N3 C7 120.6(2) . . ?
C8 N3 C18 118.8(2) . . ?
C7 N3 C18 120.5(2) . . ?
C12 N4 C13 125.4(2) . . ?
C13 N5 C14 120.6(3) . . ?
C13 N5 C19 120.4(2) . . ?
C14 N5 C19 119.0(2) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 C12 118.3(3) . . ?
C2 C1 C12 118.3(3) . . ?
C3 C2 C1 118.4(3) . . ?
C4 C3 C2 119.2(3) . . ?
C3 C4 C5 117.9(3) . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 C6 118.6(3) . . ?
C4 C5 C6 117.2(3) . . ?
O1 C6 N2 122.9(3) . . ?
O1 C6 C5 122.1(3) . . ?
N2 C6 C5 115.0(2) . . ?
N3 C7 C11 119.8(3) . . ?
N3 C7 N2 117.7(3) . . ?
C11 C7 N2 122.4(3) . . ?
N3 C8 C9 121.1(3) . . ?
C8 C9 C10 119.1(3) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 C7 119.7(3) . . ?
O2 C12 N4 124.4(3) . . ?
O2 C12 C1 122.2(3) . . ?
N4 C12 C1 113.4(3) . . ?
N5 C13 N4 116.7(2) . . ?
N5 C13 C17 119.6(3) . . ?
N4 C13 C17 123.7(3) . . ?
N5 C14 C15 121.1(3) . . ?
C14 C15 C16 118.9(3) . . ?
C17 C16 C15 120.1(3) . . ?
C16 C17 C13 119.6(3) . . ?
F1 C20 F3 107.0(2) . . ?
F1 C20 F2 107.2(2) . . ?
F3 C20 F2 107.5(2) . . ?
F1 C20 S1 112.1(2) . . ?
F3 C20 S1 111.6(2) . . ?
F2 C20 S1 111.1(2) . . ?
O5 S1 O3 115.59(14) . . ?
O5 S1 O4 115.01(13) . . ?
O3 S1 O4 115.26(14) . . ?
O5 S1 C20 103.91(14) . . ?
O3 S1 C20 102.78(13) . . ?
O4 S1 C20 101.50(13) . . ?
F6 C21 F4 107.8(2) . . ?
F6 C21 F5 106.6(2) . . ?
F4 C21 F5 107.1(2) . . ?
F6 C21 S2 111.8(2) . . ?
F4 C21 S2 112.2(2) . . ?
F5 C21 S2 111.05(19) . . ?
O7 S2 O6 115.10(15) . . ?
O7 S2 O8 115.65(14) . . ?
O6 S2 O8 114.53(14) . . ?
O7 S2 C21 102.68(13) . . ?
O6 S2 C21 103.41(13) . . ?
O8 S2 C21 102.91(14) . . ?
C35 N31 C31 116.5(2) . . ?
C36 N32 C37 123.3(2) . . ?
C37 N33 C38 120.3(2) . . ?
C37 N33 C48 121.4(2) . . ?
C38 N33 C48 118.3(2) . . ?
C42 N34 C43 124.2(3) . . ?
C43 N35 C44 120.7(2) . . ?
C43 N35 C49 121.2(2) . . ?
C44 N35 C49 118.1(2) . . ?
N31 C31 C32 123.8(3) . . ?
N31 C31 C42 118.4(3) . . ?
C32 C31 C42 117.7(3) . . ?
C33 C32 C31 118.2(3) . . ?
C34 C33 C32 119.3(3) . . ?
C33 C34 C35 118.2(3) . . ?
N31 C35 C34 123.9(3) . . ?
N31 C35 C36 118.8(2) . . ?
C34 C35 C36 117.3(3) . . ?
O31 C36 N32 123.7(3) . . ?
O31 C36 C35 121.9(3) . . ?
N32 C36 C35 114.4(3) . . ?
N33 C37 N32 117.4(3) . . ?
N33 C37 C41 119.4(3) . . ?
N32 C37 C41 123.1(3) . . ?
C39 C38 N33 121.6(3) . . ?
C38 C39 C40 119.0(3) . . ?
C41 C40 C39 119.4(3) . . ?
C40 C41 C37 120.3(3) . . ?
O32 C42 N34 124.1(3) . . ?
O32 C42 C31 122.4(3) . . ?
N34 C42 C31 113.5(3) . . ?
N35 C43 N34 116.3(3) . . ?
N35 C43 C47 119.4(3) . . ?
N34 C43 C47 124.3(3) . . ?
N35 C44 C45 121.0(3) . . ?
C44 C45 C46 119.1(3) . . ?
C47 C46 C45 119.9(3) . . ?
C46 C47 C43 119.8(3) . . ?
F31 C50 F33 107.7(2) . . ?
F31 C50 F32 107.7(2) . . ?
F33 C50 F32 107.8(2) . . ?
F31 C50 S31 111.1(2) . . ?
F33 C50 S31 111.4(2) . . ?
F32 C50 S31 110.9(2) . . ?
O35 S31 O34 115.54(14) . . ?
O35 S31 O33 114.91(13) . . ?
O34 S31 O33 114.15(13) . . ?
O35 S31 C50 103.77(13) . . ?
O34 S31 C50 103.12(13) . . ?
O33 S31 C50 103.02(14) . . ?
F36 C51 F35 107.3(2) . . ?
F36 C51 F34 107.2(2) . . ?
F35 C51 F34 107.3(2) . . ?
F36 C51 S32 111.4(2) . . ?
F35 C51 S32 111.7(2) . . ?
F34 C51 S32 111.7(2) . . ?
O36 S32 O37 115.97(14) . . ?
O36 S32 O38 115.46(13) . . ?
O37 S32 O38 114.67(13) . . ?
O36 S32 C51 103.10(14) . . ?
O37 S32 C51 102.77(13) . . ?
O38 S32 C51 101.96(13) . . ?
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
N1 C5 1.326(4) . ?
N1 C1 1.344(4) . ?
N2 C6 1.374(4) . ?
N2 C7 1.394(4) . ?
N3 C8 1.349(4) . ?
N3 C7 1.352(4) . ?
N3 C18 1.482(4) . ?
N4 C12 1.376(4) . ?
N4 C13 1.382(4) . ?
N5 C13 1.355(4) . ?
N5 C14 1.357(4) . ?
N5 C19 1.476(4) . ?
O1 C6 1.209(4) . ?
O2 C12 1.210(4) . ?
C1 C2 1.387(4) . ?
C1 C12 1.498(4) . ?
C2 C3 1.385(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.396(4) . ?
C5 C6 1.502(4) . ?
C7 C11 1.380(4) . ?
C8 C9 1.364(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.378(4) . ?
C13 C17 1.390(4) . ?
C14 C15 1.364(4) . ?
C15 C16 1.385(4) . ?
C16 C17 1.372(4) . ?
C20 F1 1.334(3) . ?
C20 F3 1.334(3) . ?
C20 F2 1.338(3) . ?
C20 S1 1.819(3) . ?
S1 O5 1.433(2) . ?
S1 O3 1.441(2) . ?
S1 O4 1.441(2) . ?
C21 F6 1.328(3) . ?
C21 F4 1.329(3) . ?
C21 F5 1.342(3) . ?
C21 S2 1.826(3) . ?
S2 O7 1.434(2) . ?
S2 O6 1.438(2) . ?
S2 O8 1.440(2) . ?
N31 C35 1.335(4) . ?
N31 C31 1.341(4) . ?
N32 C36 1.382(4) . ?
N32 C37 1.387(4) . ?
N33 C37 1.353(4) . ?
N33 C38 1.361(4) . ?
N33 C48 1.479(4) . ?
N34 C42 1.381(4) . ?
N34 C43 1.384(4) . ?
N35 C43 1.357(4) . ?
N35 C44 1.360(4) . ?
N35 C49 1.475(4) . ?
O31 C36 1.202(4) . ?
O32 C42 1.208(4) . ?
C31 C32 1.387(4) . ?
C31 C42 1.504(4) . ?
C32 C33 1.380(4) . ?
C33 C34 1.377(4) . ?
C34 C35 1.389(4) . ?
C35 C36 1.504(4) . ?
C37 C41 1.391(4) . ?
C38 C39 1.356(4) . ?
C39 C40 1.394(4) . ?
C40 C41 1.368(4) . ?
C43 C47 1.388(4) . ?
C44 C45 1.362(4) . ?
C45 C46 1.384(4) . ?
C46 C47 1.375(4) . ?
C50 F31 1.332(3) . ?
C50 F33 1.332(3) . ?
C50 F32 1.332(3) . ?
C50 S31 1.835(3) . ?
S31 O35 1.432(2) . ?
S31 O34 1.441(2) . ?
S31 O33 1.442(2) . ?
C51 F36 1.336(3) . ?
C51 F35 1.336(3) . ?
C51 F34 1.336(3) . ?
C51 S32 1.825(3) . ?
S32 O36 1.432(2) . ?
S32 O37 1.440(2) . ?
S32 O38 1.443(2) . ?
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
C5 N1 C1 C2 -1.2(4) . . . . ?
C5 N1 C1 C12 178.9(3) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
C12 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C1 N1 C5 C4 -0.4(4) . . . . ?
C1 N1 C5 C6 177.9(3) . . . . ?
C3 C4 C5 N1 1.7(5) . . . . ?
C3 C4 C5 C6 -176.7(3) . . . . ?
C7 N2 C6 O1 12.2(5) . . . . ?
C7 N2 C6 C5 -167.4(3) . . . . ?
N1 C5 C6 O1 172.5(3) . . . . ?
C4 C5 C6 O1 -9.0(4) . . . . ?
N1 C5 C6 N2 -7.8(4) . . . . ?
C4 C5 C6 N2 170.7(3) . . . . ?
C8 N3 C7 C11 2.8(4) . . . . ?
C18 N3 C7 C11 -177.8(3) . . . . ?
C8 N3 C7 N2 -178.2(3) . . . . ?
C18 N3 C7 N2 1.2(4) . . . . ?
C6 N2 C7 N3 -138.8(3) . . . . ?
C6 N2 C7 C11 40.2(4) . . . . ?
C7 N3 C8 C9 -2.9(4) . . . . ?
C18 N3 C8 C9 177.7(3) . . . . ?
N3 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C7 -0.4(5) . . . . ?
N3 C7 C11 C10 -1.1(4) . . . . ?
N2 C7 C11 C10 179.9(3) . . . . ?
C13 N4 C12 O2 8.1(5) . . . . ?
C13 N4 C12 C1 -172.8(3) . . . . ?
N1 C1 C12 O2 169.8(3) . . . . ?
C2 C1 C12 O2 -10.2(4) . . . . ?
N1 C1 C12 N4 -9.4(4) . . . . ?
C2 C1 C12 N4 170.7(3) . . . . ?
C14 N5 C13 N4 -175.5(3) . . . . ?
C19 N5 C13 N4 5.0(4) . . . . ?
C14 N5 C13 C17 1.8(4) . . . . ?
C19 N5 C13 C17 -177.7(3) . . . . ?
C12 N4 C13 N5 -158.3(3) . . . . ?
C12 N4 C13 C17 24.5(5) . . . . ?
C13 N5 C14 C15 -1.5(4) . . . . ?
C19 N5 C14 C15 178.1(3) . . . . ?
N5 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C13 0.7(5) . . . . ?
N5 C13 C17 C16 -1.4(4) . . . . ?
N4 C13 C17 C16 175.7(3) . . . . ?
F1 C20 S1 O5 61.0(2) . . . . ?
F3 C20 S1 O5 -59.0(2) . . . . ?
F2 C20 S1 O5 -179.03(19) . . . . ?
F1 C20 S1 O3 -59.8(2) . . . . ?
F3 C20 S1 O3 -179.8(2) . . . . ?
F2 C20 S1 O3 60.1(2) . . . . ?
F1 C20 S1 O4 -179.3(2) . . . . ?
F3 C20 S1 O4 60.6(2) . . . . ?
F2 C20 S1 O4 -59.4(2) . . . . ?
F6 C21 S2 O7 -58.3(2) . . . . ?
F4 C21 S2 O7 63.0(2) . . . . ?
F5 C21 S2 O7 -177.2(2) . . . . ?
F6 C21 S2 O6 -178.3(2) . . . . ?
F4 C21 S2 O6 -57.0(2) . . . . ?
F5 C21 S2 O6 62.8(2) . . . . ?
F6 C21 S2 O8 62.2(2) . . . . ?
F4 C21 S2 O8 -176.5(2) . . . . ?
F5 C21 S2 O8 -56.7(2) . . . . ?
C35 N31 C31 C32 -0.3(4) . . . . ?
C35 N31 C31 C42 -179.4(3) . . . . ?
N31 C31 C32 C33 0.1(5) . . . . ?
C42 C31 C32 C33 179.2(3) . . . . ?
C31 C32 C33 C34 0.1(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C31 N31 C35 C34 0.4(4) . . . . ?
C31 N31 C35 C36 179.5(3) . . . . ?
C33 C34 C35 N31 -0.2(5) . . . . ?
C33 C34 C35 C36 -179.4(3) . . . . ?
C37 N32 C36 O31 12.0(5) . . . . ?
C37 N32 C36 C35 -169.5(3) . . . . ?
N31 C35 C36 O31 171.9(3) . . . . ?
C34 C35 C36 O31 -8.8(4) . . . . ?
N31 C35 C36 N32 -6.7(4) . . . . ?
C34 C35 C36 N32 172.6(3) . . . . ?
C38 N33 C37 N32 -179.9(3) . . . . ?
C48 N33 C37 N32 -2.2(4) . . . . ?
C38 N33 C37 C41 -0.4(4) . . . . ?
C48 N33 C37 C41 177.3(3) . . . . ?
C36 N32 C37 N33 -154.3(3) . . . . ?
C36 N32 C37 C41 26.1(4) . . . . ?
C37 N33 C38 C39 -1.3(4) . . . . ?
C48 N33 C38 C39 -179.0(3) . . . . ?
N33 C38 C39 C40 2.1(5) . . . . ?
C38 C39 C40 C41 -1.2(5) . . . . ?
C39 C40 C41 C37 -0.4(5) . . . . ?
N33 C37 C41 C40 1.2(4) . . . . ?
N32 C37 C41 C40 -179.3(3) . . . . ?
C43 N34 C42 O32 6.1(5) . . . . ?
C43 N34 C42 C31 -174.5(3) . . . . ?
N31 C31 C42 O32 166.5(3) . . . . ?
C32 C31 C42 O32 -12.6(4) . . . . ?
N31 C31 C42 N34 -12.9(4) . . . . ?
C32 C31 C42 N34 167.9(3) . . . . ?
C44 N35 C43 N34 -176.6(3) . . . . ?
C49 N35 C43 N34 3.6(4) . . . . ?
C44 N35 C43 C47 1.4(4) . . . . ?
C49 N35 C43 C47 -178.4(3) . . . . ?
C42 N34 C43 N35 -152.6(3) . . . . ?
C42 N34 C43 C47 29.6(5) . . . . ?
C43 N35 C44 C45 -0.7(4) . . . . ?
C49 N35 C44 C45 179.1(3) . . . . ?
N35 C44 C45 C46 -0.1(4) . . . . ?
C44 C45 C46 C47 0.0(5) . . . . ?
C45 C46 C47 C43 0.7(5) . . . . ?
N35 C43 C47 C46 -1.5(4) . . . . ?
N34 C43 C47 C46 176.3(3) . . . . ?
F31 C50 S31 O35 -58.5(2) . . . . ?
F33 C50 S31 O35 61.6(2) . . . . ?
F32 C50 S31 O35 -178.2(2) . . . . ?
F31 C50 S31 O34 -179.4(2) . . . . ?
F33 C50 S31 O34 -59.2(2) . . . . ?
F32 C50 S31 O34 60.9(2) . . . . ?
F31 C50 S31 O33 61.6(2) . . . . ?
F33 C50 S31 O33 -178.3(2) . . . . ?
F32 C50 S31 O33 -58.1(2) . . . . ?
F36 C51 S32 O36 54.5(2) . . . . ?
F35 C51 S32 O36 174.5(2) . . . . ?
F34 C51 S32 O36 -65.3(2) . . . . ?
F36 C51 S32 O37 175.5(2) . . . . ?
F35 C51 S32 O37 -64.5(2) . . . . ?
F34 C51 S32 O37 55.6(2) . . . . ?
F36 C51 S32 O38 -65.5(2) . . . . ?
F35 C51 S32 O38 54.5(2) . . . . ?
F34 C51 S32 O38 174.6(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091447
