#------------------------------------------------------------------------------
#$Date: 2018-04-07 05:25:48 +0300 (Sat, 07 Apr 2018) $
#$Revision: 207260 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/92/1549231.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1549231
loop_
_publ_author_name
'Rehman, Abida'
'Delori, Amit'
'Hughes, David S.'
'Jones, William'
_publ_section_title
;
 Structural studies of crystalline forms of triamterene with carboxylic
 acid, GRAS and API molecules
;
_journal_issue                   3
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252518003317
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         '2(C12 H12 N7), C6 H8 O4, 2(C2 H6 O S)'
_chemical_formula_sum            'C34 H44 N14 O6 S2'
_chemical_formula_weight         808.95
_chemical_name_common            'Triamterene, adipic acid and DMSO'
_chemical_name_systematic
;
 Triamterenium adipate, DMSO solvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                115.247(2)
_cell_angle_beta                 109.951(4)
_cell_angle_gamma                90.122(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0286(3)
_cell_length_b                   13.7429(4)
_cell_length_c                   14.9742(5)
_cell_measurement_reflns_used    40707
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_cell_volume                     1900.25(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25204
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         25.372
_diffrn_reflns_theta_min         3.555
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.614
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         6951
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0749P)²+4.0839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5118
_reflns_number_total             6951
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5012.cif
_cod_data_source_block           1c_DMSO
_cod_original_cell_volume        1900.24(11)
_cod_database_code               1549231
_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   0.976
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
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
N1A N 0.3191(3) 0.2248(2) 0.1399(2) 0.0278(6) Uani 1 1 d . . . . .
C2A C 0.2342(3) 0.2886(3) 0.1739(3) 0.0282(7) Uani 1 1 d . . . . .
N2A N 0.2583(3) 0.3930(2) 0.1995(3) 0.0369(7) Uani 1 1 d . . . . .
H3A H 0.2043 0.4363 0.2202 0.044 Uiso 1 1 calc R U . . .
H2A H 0.3282 0.4194 0.1959 0.044 Uiso 1 1 calc R U . . .
N3A N 0.1270(3) 0.2501(2) 0.1800(2) 0.0287(6) Uani 1 1 d . . . . .
C4A C 0.1028(3) 0.1430(3) 0.1529(3) 0.0263(7) Uani 1 1 d . . . . .
C4AA C 0.1927(3) 0.0729(3) 0.1223(3) 0.0258(7) Uani 1 1 d . . . . .
N4A N -0.0044(3) 0.1035(2) 0.1547(2) 0.0316(7) Uani 1 1 d . . . . .
H4A H -0.0593 0.1469 0.1734 0.038 Uiso 1 1 calc R U . . .
H5A H -0.0214 0.0338 0.1371 0.038 Uiso 1 1 calc R U . . .
N5A N 0.1757(3) -0.0320(2) 0.1071(2) 0.0276(6) Uani 1 1 d . . . . .
C6A C 0.2613(3) -0.0922(3) 0.0799(3) 0.0268(7) Uani 1 1 d . . . . .
C7A C 0.3626(3) -0.0504(3) 0.0571(3) 0.0283(7) Uani 1 1 d . . . . .
N7A N 0.4380(3) -0.1160(3) 0.0157(3) 0.0350(7) Uani 1 1 d . . . . .
N8A N 0.3825(3) 0.0542(2) 0.0770(2) 0.0277(6) Uani 1 1 d . . . . .
C8AA C 0.2991(3) 0.1156(3) 0.1126(3) 0.0259(7) Uani 1 1 d . . . . .
C9A C 0.2507(3) -0.2024(3) 0.0749(3) 0.0281(7) Uani 1 1 d . . . . .
C10A C 0.1383(4) -0.2807(3) 0.0047(3) 0.0355(8) Uani 1 1 d . . . . .
H10A H 0.0702 -0.2657 -0.0446 0.043 Uiso 1 1 calc R U . . .
C11A C 0.1248(4) -0.3801(3) 0.0059(3) 0.0410(9) Uani 1 1 d . . . . .
H11A H 0.0489 -0.4338 -0.0435 0.049 Uiso 1 1 calc R U . . .
C12A C 0.2224(4) -0.4008(3) 0.0793(3) 0.0403(9) Uani 1 1 d . . . . .
H12A H 0.2123 -0.4684 0.0815 0.048 Uiso 1 1 calc R U . . .
C13A C 0.3342(4) -0.3244(3) 0.1494(3) 0.0340(8) Uiso 1 1 d . . . . .
H13A H 0.4008 -0.3392 0.1997 0.041 Uiso 1 1 calc R U . . .
C14A C 0.3494(4) -0.2254(3) 0.1465(3) 0.0319(8) Uiso 1 1 d . . . . .
H14A H 0.4276 -0.1735 0.1935 0.038 Uiso 1 1 calc R U . . .
N1B N 0.3412(3) 0.7274(2) 0.6746(2) 0.0264(6) Uani 1 1 d . . . . .
C2B C 0.2728(3) 0.7927(3) 0.7304(3) 0.0271(7) Uani 1 1 d . . . . .
N2B N 0.3006(3) 0.8988(2) 0.7636(2) 0.0330(7) Uani 1 1 d . . . . .
H3B H 0.2578 0.9436 0.7988 0.040 Uiso 1 1 calc R U . . .
H2B H 0.3621 0.9248 0.7505 0.040 Uiso 1 1 calc R U . . .
N3B N 0.1786(3) 0.7550(2) 0.7514(2) 0.0283(6) Uani 1 1 d . . . . .
C4B C 0.1492(3) 0.6471(3) 0.7147(3) 0.0296(8) Uani 1 1 d . . . . .
N4B N 0.0531(3) 0.6080(2) 0.7311(3) 0.0379(8) Uani 1 1 d . . . . .
H4B H 0.0098 0.6530 0.7657 0.045 Uiso 1 1 calc R U . . .
H5B H 0.0325 0.5372 0.7074 0.045 Uiso 1 1 calc R U . . .
C4AB C 0.2170(3) 0.5734(3) 0.6559(3) 0.0272(7) Uani 1 1 d . . . . .
N5B N 0.1853(3) 0.4641(2) 0.6194(2) 0.0279(6) Uani 1 1 d . . . . .
C6B C 0.2464(3) 0.3995(3) 0.5629(3) 0.0256(7) Uani 1 1 d . . . . .
C7B C 0.3414(3) 0.4440(3) 0.5364(3) 0.0271(7) Uani 1 1 d . . . . .
N7B N 0.3961(3) 0.3771(3) 0.4725(3) 0.0364(8) Uani 1 1 d . . . . .
N8B N 0.3748(3) 0.5520(2) 0.5745(2) 0.0280(6) Uani 1 1 d . . . . .
C8AB C 0.3126(3) 0.6159(3) 0.6349(3) 0.0259(7) Uani 1 1 d . . . . .
C9B C 0.2127(3) 0.2808(3) 0.5274(3) 0.0282(7) Uani 1 1 d . . . . .
C10B C 0.1146(4) 0.2160(3) 0.4304(3) 0.0401(9) Uani 1 1 d . . . . .
H10B H 0.0752 0.2456 0.3826 0.048 Uiso 1 1 calc R U . . .
C11B C 0.0728(4) 0.1076(3) 0.4016(3) 0.0463(10) Uani 1 1 d . . . . .
H11B H 0.0047 0.0636 0.3346 0.056 Uiso 1 1 calc R U . . .
C12B C 0.1299(4) 0.0642(3) 0.4700(3) 0.0445(10) Uani 1 1 d . . . . .
H12B H 0.0998 -0.0094 0.4511 0.053 Uiso 1 1 calc R U . . .
C13B C 0.2306(4) 0.1272(3) 0.5659(3) 0.0451(10) Uani 1 1 d . . . . .
H13B H 0.2719 0.0961 0.6119 0.054 Uiso 1 1 calc R U . . .
C14B C 0.2724(4) 0.2355(3) 0.5957(3) 0.0382(9) Uani 1 1 d . . . . .
H14B H 0.3413 0.2789 0.6624 0.046 Uiso 1 1 calc R U . . .
C1C C 0.4875(3) 0.0816(3) 0.3554(3) 0.0288(8) Uani 1 1 d . . . . .
O1C O 0.4799(3) 0.17533(19) 0.3599(2) 0.0354(6) Uani 1 1 d . . . . .
C2C C 0.3924(4) 0.0374(3) 0.3879(3) 0.0330(8) Uani 1 1 d . . . . .
H1C H 0.3144 -0.0076 0.3230 0.040 Uiso 1 1 calc R U . . .
H2C H 0.3629 0.0998 0.4349 0.040 Uiso 1 1 calc R U . . .
O2C O 0.5644(3) 0.0226(2) 0.3227(2) 0.0423(7) Uani 1 1 d . . . . .
C3C C 0.4463(4) -0.0317(3) 0.4457(3) 0.0334(8) Uani 1 1 d . . . . .
H3C H 0.3735 -0.0649 0.4537 0.040 Uiso 1 1 calc R U . . .
H4C H 0.4806 -0.0919 0.4007 0.040 Uiso 1 1 calc R U . . .
C1D C 0.5282(3) 0.4207(3) 0.1422(3) 0.0270(7) Uani 1 1 d . . . . .
O1D O 0.5016(3) 0.31838(19) 0.1063(2) 0.0367(6) Uani 1 1 d . . . . .
C2D C 0.6224(3) 0.4627(3) 0.1068(3) 0.0313(8) Uani 1 1 d . . . . .
H1D H 0.6495 0.3996 0.0582 0.038 Uiso 1 1 calc R U . . .
H2D H 0.7018 0.5078 0.1700 0.038 Uiso 1 1 calc R U . . .
O2D O 0.4832(2) 0.48912(19) 0.2044(2) 0.0340(6) Uani 1 1 d . . . . .
C3D C 0.5618(3) 0.5307(3) 0.0497(3) 0.0302(8) Uani 1 1 d . . . . .
H3D H 0.5405 0.5964 0.1001 0.036 Uiso 1 1 calc R U . . .
H4D H 0.6276 0.5558 0.0292 0.036 Uiso 1 1 calc R U . . .
S1E S 0.16128(11) 0.67740(8) 0.32485(8) 0.0452(3) Uani 1 1 d D . . . .
O1E O 0.0858(3) 0.5633(2) 0.2590(2) 0.0462(7) Uani 1 1 d D . . . .
C1E C 0.3249(4) 0.6647(4) 0.3889(3) 0.0499(11) Uani 1 1 d D . . . .
H1E H 0.3640 0.6302 0.3355 0.075 Uiso 1 1 calc R U . . .
H2E H 0.3245 0.6197 0.4249 0.075 Uiso 1 1 calc R U . . .
H3E H 0.3764 0.7374 0.4414 0.075 Uiso 1 1 calc R U . . .
C2E C 0.1180(6) 0.7352(4) 0.4396(4) 0.0682(14) Uani 1 1 d D . . . .
H4E H 0.0298 0.7530 0.4194 0.102 Uiso 1 1 calc R U . . .
H5E H 0.1808 0.8019 0.4944 0.102 Uiso 1 1 calc R U . . .
H6E H 0.1197 0.6825 0.4678 0.102 Uiso 1 1 calc R U . . .
S1F S 0.14448(15) 1.14703(12) 0.80626(12) 0.0427(4) Uani 0.7 1 d D . P A 1
O1F O 0.1590(7) 1.0752(4) 0.8691(4) 0.0483(6) Uiso 0.7 1 d D U P A 1
C1F C 0.3122(6) 1.1906(6) 0.8335(6) 0.0483(6) Uiso 0.7 1 d D U P A 1
H1F H 0.3486 1.1276 0.7968 0.072 Uiso 0.7 1 calc R U P A 1
H2F H 0.3626 1.2232 0.9105 0.072 Uiso 0.7 1 calc R U P A 1
H3F H 0.3169 1.2449 0.8080 0.072 Uiso 0.7 1 calc R U P A 1
C2F C 0.1117(6) 1.2723(5) 0.8905(5) 0.0483(6) Uiso 0.7 1 d D U P A 1
H4F H 0.0242 1.2606 0.8907 0.072 Uiso 0.7 1 calc R U P A 1
H5F H 0.1158 1.3259 0.8641 0.072 Uiso 0.7 1 calc R U P A 1
H6F H 0.1771 1.2996 0.9632 0.072 Uiso 0.7 1 calc R U P A 1
S1F' S 0.1649(4) 1.1878(3) 0.8959(3) 0.0483(6) Uiso 0.3 1 d D U P B 2
O1F' O 0.1441(15) 1.0650(9) 0.8489(10) 0.0483(6) Uiso 0.3 1 d D U P B 2
C1F' C 0.2704(13) 1.2054(13) 0.8312(13) 0.0483(6) Uiso 0.3 1 d D U P B 2
H1F' H 0.3623 1.2164 0.8775 0.072 Uiso 0.3 1 calc R U P B 2
H2F' H 0.2544 1.2692 0.8182 0.072 Uiso 0.3 1 calc R U P B 2
H3F' H 0.2513 1.1401 0.7632 0.072 Uiso 0.3 1 calc R U P B 2
C2F' C 0.0143(12) 1.1951(12) 0.8031(11) 0.0483(6) Uiso 0.3 1 d D U P B 2
H4F' H -0.0590 1.1512 0.7995 0.072 Uiso 0.3 1 calc R U P B 2
H5F' H 0.0187 1.1667 0.7323 0.072 Uiso 0.3 1 calc R U P B 2
H6F' H 0.0014 1.2713 0.8271 0.072 Uiso 0.3 1 calc R U P B 2
H1XA H 0.375(4) 0.253(3) 0.128(3) 0.038(11) Uiso 1 1 d . . . . .
H1XB H 0.410(5) 0.761(4) 0.670(4) 0.075(16) Uiso 1 1 d . . . . .
H6A H 0.422(4) -0.184(3) -0.006(3) 0.029(10) Uiso 1 1 d . . . . .
H7A H 0.489(4) -0.091(4) -0.001(3) 0.043(12) Uiso 1 1 d . . . . .
H6B H 0.381(4) 0.310(3) 0.453(3) 0.032(10) Uiso 1 1 d . . . . .
H7B H 0.455(5) 0.403(4) 0.458(3) 0.047(12) Uiso 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'
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
C2A N1A C8AA 120.0(3) .
C2A N1A H1XA 117(3) .
C8AA N1A H1XA 122(3) .
N2A C2A N3A 119.0(3) .
N2A C2A N1A 117.6(3) .
N3A C2A N1A 123.4(3) .
C2A N2A H3A 120.0 .
C2A N2A H2A 120.0 .
H3A N2A H2A 120.0 .
C2A N3A C4A 118.5(3) .
N4A C4A N3A 119.1(3) .
N4A C4A C4AA 120.3(3) .
N3A C4A C4AA 120.6(3) .
N5A C4AA C8AA 121.2(3) .
N5A C4AA C4A 120.2(3) .
C8AA C4AA C4A 118.6(3) .
C4A N4A H4A 120.0 .
C4A N4A H5A 120.0 .
H4A N4A H5A 120.0 .
C6A N5A C4AA 117.6(3) .
N5A C6A C7A 120.4(3) .
N5A C6A C9A 117.3(3) .
C7A C6A C9A 122.4(3) .
N7A C7A N8A 118.3(3) .
N7A C7A C6A 120.4(3) .
N8A C7A C6A 121.4(3) .
C7A N7A H6A 121(3) .
C7A N7A H7A 117(3) .
H6A N7A H7A 120(4) .
C7A N8A C8AA 116.1(3) .
N8A C8AA N1A 118.7(3) .
N8A C8AA C4AA 122.6(3) .
N1A C8AA C4AA 118.7(3) .
C14A C9A C10A 119.1(3) .
C14A C9A C6A 119.9(3) .
C10A C9A C6A 120.9(3) .
C11A C10A C9A 120.6(4) .
C11A C10A H10A 119.7 .
C9A C10A H10A 119.7 .
C10A C11A C12A 119.6(4) .
C10A C11A H11A 120.2 .
C12A C11A H11A 120.2 .
C13A C12A C11A 120.5(4) .
C13A C12A H12A 119.7 .
C11A C12A H12A 119.7 .
C12A C13A C14A 119.9(3) .
C12A C13A H13A 120.0 .
C14A C13A H13A 120.0 .
C9A C14A C13A 120.1(3) .
C9A C14A H14A 119.9 .
C13A C14A H14A 119.9 .
C2B N1B C8AB 119.5(3) .
C2B N1B H1XB 118(3) .
C8AB N1B H1XB 123(3) .
N2B C2B N3B 118.9(3) .
N2B C2B N1B 117.2(3) .
N3B C2B N1B 123.9(3) .
C2B N2B H3B 120.0 .
C2B N2B H2B 120.0 .
H3B N2B H2B 120.0 .
C4B N3B C2B 118.1(3) .
N4B C4B N3B 118.9(3) .
N4B C4B C4AB 119.8(3) .
N3B C4B C4AB 121.3(3) .
C4B N4B H4B 120.0 .
C4B N4B H5B 120.0 .
H4B N4B H5B 120.0 .
N5B C4AB C8AB 121.1(3) .
N5B C4AB C4B 120.2(3) .
C8AB C4AB C4B 118.7(3) .
C6B N5B C4AB 118.2(3) .
N5B C6B C7B 120.4(3) .
N5B C6B C9B 116.8(3) .
C7B C6B C9B 122.8(3) .
N7B C7B N8B 118.8(3) .
N7B C7B C6B 120.0(3) .
N8B C7B C6B 121.2(3) .
C7B N7B H6B 119(3) .
C7B N7B H7B 120(3) .
H6B N7B H7B 120(4) .
C7B N8B C8AB 116.5(3) .
N8B C8AB N1B 119.0(3) .
N8B C8AB C4AB 122.4(3) .
N1B C8AB C4AB 118.5(3) .
C10B C9B C14B 119.1(3) .
C10B C9B C6B 120.3(3) .
C14B C9B C6B 120.3(3) .
C9B C10B C11B 120.6(4) .
C9B C10B H10B 119.7 .
C11B C10B H10B 119.7 .
C12B C11B C10B 120.0(4) .
C12B C11B H11B 120.0 .
C10B C11B H11B 120.0 .
C11B C12B C13B 119.9(4) .
C11B C12B H12B 120.0 .
C13B C12B H12B 120.0 .
C12B C13B C14B 120.5(4) .
C12B C13B H13B 119.7 .
C14B C13B H13B 119.7 .
C13B C14B C9B 119.7(4) .
C13B C14B H14B 120.1 .
C9B C14B H14B 120.1 .
O2C C1C O1C 124.3(3) .
O2C C1C C2C 118.7(3) .
O1C C1C C2C 117.0(3) .
C1C C2C C3C 115.5(3) .
C1C C2C H1C 108.4 .
C3C C2C H1C 108.4 .
C1C C2C H2C 108.4 .
C3C C2C H2C 108.4 .
H1C C2C H2C 107.5 .
C3C C3C C2C 114.1(4) 2_656
C3C C3C H3C 108.7 2_656
C2C C3C H3C 108.7 .
C3C C3C H4C 108.7 2_656
C2C C3C H4C 108.7 .
H3C C3C H4C 107.6 .
O2D C1D O1D 124.7(3) .
O2D C1D C2D 118.3(3) .
O1D C1D C2D 117.0(3) .
C1D C2D C3D 112.7(3) .
C1D C2D H1D 109.1 .
C3D C2D H1D 109.1 .
C1D C2D H2D 109.1 .
C3D C2D H2D 109.1 .
H1D C2D H2D 107.8 .
C3D C3D C2D 113.8(4) 2_665
C3D C3D H3D 108.8 2_665
C2D C3D H3D 108.8 .
C3D C3D H4D 108.8 2_665
C2D C3D H4D 108.8 .
H3D C3D H4D 107.7 .
O1E S1E C1E 105.73(19) .
O1E S1E C2E 105.9(2) .
C1E S1E C2E 98.2(2) .
S1E C1E H1E 109.5 .
S1E C1E H2E 109.5 .
H1E C1E H2E 109.5 .
S1E C1E H3E 109.5 .
H1E C1E H3E 109.5 .
H2E C1E H3E 109.5 .
S1E C2E H4E 109.5 .
S1E C2E H5E 109.5 .
H4E C2E H5E 109.5 .
S1E C2E H6E 109.5 .
H4E C2E H6E 109.5 .
H5E C2E H6E 109.5 .
O1F S1F C2F 103.9(3) .
O1F S1F C1F 101.9(3) .
C2F S1F C1F 99.0(3) .
S1F C1F H1F 109.5 .
S1F C1F H2F 109.5 .
H1F C1F H2F 109.5 .
S1F C1F H3F 109.5 .
H1F C1F H3F 109.5 .
H2F C1F H3F 109.5 .
S1F C2F H4F 109.5 .
S1F C2F H5F 109.5 .
H4F C2F H5F 109.5 .
S1F C2F H6F 109.5 .
H4F C2F H6F 109.5 .
H5F C2F H6F 109.5 .
O1F' S1F' C2F' 96.2(7) .
O1F' S1F' C1F' 98.6(8) .
C2F' S1F' C1F' 96.6(7) .
S1F' C1F' H1F' 109.5 .
S1F' C1F' H2F' 109.5 .
H1F' C1F' H2F' 109.5 .
S1F' C1F' H3F' 109.5 .
H1F' C1F' H3F' 109.5 .
H2F' C1F' H3F' 109.5 .
S1F' C2F' H4F' 109.5 .
S1F' C2F' H5F' 109.5 .
H4F' C2F' H5F' 109.5 .
S1F' C2F' H6F' 109.5 .
H4F' C2F' H6F' 109.5 .
H5F' C2F' H6F' 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1A C2A 1.361(4) .
N1A C8AA 1.372(4) .
N1A H1XA 0.83(4) .
C2A N2A 1.317(4) .
C2A N3A 1.341(4) .
N2A H3A 0.8800 .
N2A H2A 0.8800 .
N3A C4A 1.348(4) .
C4A N4A 1.314(4) .
C4A C4AA 1.435(4) .
C4AA N5A 1.362(4) .
C4AA C8AA 1.389(5) .
N4A H4A 0.8800 .
N4A H5A 0.8800 .
N5A C6A 1.311(4) .
C6A C7A 1.455(5) .
C6A C9A 1.487(5) .
C7A N7A 1.329(4) .
C7A N8A 1.339(4) .
N7A H6A 0.84(4) .
N7A H7A 0.81(5) .
N8A C8AA 1.340(4) .
C9A C14A 1.389(5) .
C9A C10A 1.393(5) .
C10A C11A 1.381(5) .
C10A H10A 0.9500 .
C11A C12A 1.383(6) .
C11A H11A 0.9500 .
C12A C13A 1.376(6) .
C12A H12A 0.9500 .
C13A C14A 1.391(5) .
C13A H13A 0.9500 .
C14A H14A 0.9500 .
N1B C2B 1.367(4) .
N1B C8AB 1.376(4) .
N1B H1XB 0.92(6) .
C2B N2B 1.321(4) .
C2B N3B 1.345(4) .
N2B H3B 0.8800 .
N2B H2B 0.8800 .
N3B C4B 1.336(4) .
C4B N4B 1.328(4) .
C4B C4AB 1.432(5) .
N4B H4B 0.8800 .
N4B H5B 0.8800 .
C4AB N5B 1.358(4) .
C4AB C8AB 1.391(5) .
N5B C6B 1.307(4) .
C6B C7B 1.456(5) .
C6B C9B 1.484(5) .
C7B N7B 1.330(4) .
C7B N8B 1.339(4) .
N7B H6B 0.83(4) .
N7B H7B 0.86(5) .
N8B C8AB 1.345(4) .
C9B C10B 1.376(5) .
C9B C14B 1.398(5) .
C10B C11B 1.389(5) .
C10B H10B 0.9500 .
C11B C12B 1.373(6) .
C11B H11B 0.9500 .
C12B C13B 1.376(6) .
C12B H12B 0.9500 .
C13B C14B 1.385(5) .
C13B H13B 0.9500 .
C14B H14B 0.9500 .
C1C O2C 1.251(4) .
C1C O1C 1.266(4) .
C1C C2C 1.518(5) .
C2C C3C 1.534(5) .
C2C H1C 0.9900 .
C2C H2C 0.9900 .
C3C C3C 1.510(7) 2_656
C3C H3C 0.9900 .
C3C H4C 0.9900 .
C1D O2D 1.253(4) .
C1D O1D 1.265(4) .
C1D C2D 1.525(5) .
C2D C3D 1.532(5) .
C2D H1D 0.9900 .
C2D H2D 0.9900 .
C3D C3D 1.525(7) 2_665
C3D H3D 0.9900 .
C3D H4D 0.9900 .
S1E O1E 1.497(3) .
S1E C1E 1.780(4) .
S1E C2E 1.791(5) .
C1E H1E 0.9800 .
C1E H2E 0.9800 .
C1E H3E 0.9800 .
C2E H4E 0.9800 .
C2E H5E 0.9800 .
C2E H6E 0.9800 .
S1F O1F 1.605(6) .
S1F C2F 1.773(6) .
S1F C1F 1.794(6) .
C1F H1F 0.9800 .
C1F H2F 0.9800 .
C1F H3F 0.9800 .
C2F H4F 0.9800 .
C2F H5F 0.9800 .
C2F H6F 0.9800 .
S1F' O1F' 1.507(11) .
S1F' C2F' 1.800(11) .
S1F' C1F' 1.821(12) .
C1F' H1F' 0.9800 .
C1F' H2F' 0.9800 .
C1F' H3F' 0.9800 .
C2F' H4F' 0.9800 .
C2F' H5F' 0.9800 .
C2F' H6F' 0.9800 .
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_4
C8AA N1A C2A N2A 179.7(3) .
C8AA N1A C2A N3A -2.0(5) .
N2A C2A N3A C4A 179.5(3) .
N1A C2A N3A C4A 1.3(5) .
C2A N3A C4A N4A -177.5(3) .
C2A N3A C4A C4AA 2.4(5) .
N4A C4A C4AA N5A -7.7(5) .
N3A C4A C4AA N5A 172.3(3) .
N4A C4A C4AA C8AA 174.6(3) .
N3A C4A C4AA C8AA -5.4(5) .
C8AA C4AA N5A C6A -2.0(5) .
C4A C4AA N5A C6A -179.6(3) .
C4AA N5A C6A C7A -5.7(5) .
C4AA N5A C6A C9A 173.5(3) .
N5A C6A C7A N7A -170.9(3) .
C9A C6A C7A N7A 10.0(5) .
N5A C6A C7A N8A 9.1(5) .
C9A C6A C7A N8A -170.1(3) .
N7A C7A N8A C8AA 176.1(3) .
C6A C7A N8A C8AA -3.8(5) .
C7A N8A C8AA N1A 176.4(3) .
C7A N8A C8AA C4AA -4.0(5) .
C2A N1A C8AA N8A 178.5(3) .
C2A N1A C8AA C4AA -1.1(5) .
N5A C4AA C8AA N8A 7.4(5) .
C4A C4AA C8AA N8A -175.0(3) .
N5A C4AA C8AA N1A -173.1(3) .
C4A C4AA C8AA N1A 4.6(5) .
N5A C6A C9A C14A -113.9(4) .
C7A C6A C9A C14A 65.3(4) .
N5A C6A C9A C10A 61.2(4) .
C7A C6A C9A C10A -119.6(4) .
C14A C9A C10A C11A 0.0(5) .
C6A C9A C10A C11A -175.1(3) .
C9A C10A C11A C12A 1.6(6) .
C10A C11A C12A C13A -1.6(6) .
C11A C12A C13A C14A -0.1(5) .
C10A C9A C14A C13A -1.7(5) .
C6A C9A C14A C13A 173.5(3) .
C12A C13A C14A C9A 1.7(5) .
C8AB N1B C2B N2B -177.7(3) .
C8AB N1B C2B N3B 1.1(5) .
N2B C2B N3B C4B 178.2(3) .
N1B C2B N3B C4B -0.6(5) .
C2B N3B C4B N4B -177.5(3) .
C2B N3B C4B C4AB 0.9(5) .
N4B C4B C4AB N5B -1.7(5) .
N3B C4B C4AB N5B -180.0(3) .
N4B C4B C4AB C8AB 176.6(3) .
N3B C4B C4AB C8AB -1.7(5) .
C8AB C4AB N5B C6B -0.6(5) .
C4B C4AB N5B C6B 177.6(3) .
C4AB N5B C6B C7B -2.7(5) .
C4AB N5B C6B C9B 178.0(3) .
N5B C6B C7B N7B -175.1(3) .
C9B C6B C7B N7B 4.2(5) .
N5B C6B C7B N8B 4.3(5) .
C9B C6B C7B N8B -176.4(3) .
N7B C7B N8B C8AB 177.2(3) .
C6B C7B N8B C8AB -2.3(5) .
C7B N8B C8AB N1B -178.8(3) .
C7B N8B C8AB C4AB -1.1(5) .
C2B N1B C8AB N8B 175.9(3) .
C2B N1B C8AB C4AB -1.9(5) .
N5B C4AB C8AB N8B 2.7(5) .
C4B C4AB C8AB N8B -175.6(3) .
N5B C4AB C8AB N1B -179.6(3) .
C4B C4AB C8AB N1B 2.1(5) .
N5B C6B C9B C10B 91.3(4) .
C7B C6B C9B C10B -88.0(4) .
N5B C6B C9B C14B -83.3(4) .
C7B C6B C9B C14B 97.4(4) .
C14B C9B C10B C11B 1.7(6) .
C6B C9B C10B C11B -173.0(3) .
C9B C10B C11B C12B -0.3(6) .
C10B C11B C12B C13B -1.6(6) .
C11B C12B C13B C14B 2.1(6) .
C12B C13B C14B C9B -0.8(6) .
C10B C9B C14B C13B -1.1(5) .
C6B C9B C14B C13B 173.5(3) .
O2C C1C C2C C3C 37.8(5) .
O1C C1C C2C C3C -144.7(3) .
C1C C2C C3C C3C 66.6(5) 2_656
O2D C1D C2D C3D -58.8(4) .
O1D C1D C2D C3D 121.4(3) .
C1D C2D C3D C3D -58.9(5) 2_665
