#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026039.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_4026039
loop_
_publ_author_name
'Sung Kuk Kim'
'Dustin E. Gross'
'Dong-Gyu Cho'
'Vincent M. Lynch'
'Jonathan L. Sessler'
_publ_section_title
;
 N-Tosylpyrrolidine Calix[4]pyrrole: Synthesis and Ion Binding Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1005
_journal_page_last               1012
_journal_paper_doi               10.1021/jo101882r
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety
' C64 H72 N8 O8 S4, 4 C3 H7 N O, 1/2 C H2 Cl2'
_chemical_formula_sum            'C76.5 H101 Cl N12 O12 S4'
_chemical_formula_weight         1544.38
_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                105.0390(10)
_cell_angle_beta                 90.9620(10)
_cell_angle_gamma                107.6010(10)
_cell_formula_units_Z            2
_cell_length_a                   11.4296(6)
_cell_length_b                   12.6286(6)
_cell_length_c                   15.0391(9)
_cell_measurement_reflns_used    6881
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1987.52(18)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15170
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.581
_exptl_crystal_description       plates
_exptl_crystal_F_000             1642
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         8976
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                5979
_reflns_number_total             8976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101882r_si_001.cif
_cod_data_source_block           ksk001
_cod_original_formula_sum        'C76.50 H101 Cl N12 O12 S4'
_cod_database_code               4026039
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13041(5) -0.11490(5) 0.25275(4) 0.03201(16) Uani 1 1 d . . .
S2 S -0.10012(5) 0.39847(5) 0.30709(4) 0.02992(15) Uani 1 1 d . . .
O1 O 0.09293(13) -0.16655(13) 0.32578(11) 0.0391(4) Uani 1 1 d . . .
O2 O 0.04000(14) -0.10624(14) 0.19034(12) 0.0447(4) Uani 1 1 d . . .
O3 O -0.13855(13) 0.27514(13) 0.26576(11) 0.0387(4) Uani 1 1 d . . .
O4 O -0.15543(13) 0.44702(14) 0.38593(10) 0.0366(4) Uani 1 1 d . . .
N1 N 0.52198(16) 0.33057(16) 0.39059(12) 0.0250(4) Uani 1 1 d . . .
N2 N 0.43931(16) 0.57526(14) 0.37822(11) 0.0239(4) Uani 1 1 d . . .
N3 N 0.21873(15) 0.01652(14) 0.30217(12) 0.0286(4) Uani 1 1 d . . .
N4 N 0.04686(14) 0.43841(14) 0.33922(11) 0.0269(4) Uani 1 1 d . . .
C1 C 0.50020(17) 0.24184(17) 0.43131(13) 0.0233(4) Uani 1 1 d . . .
C2 C 0.39847(17) 0.15591(17) 0.37996(13) 0.0240(4) Uani 1 1 d . . .
C3 C 0.35879(17) 0.19406(17) 0.30839(13) 0.0246(4) Uani 1 1 d . . .
C4 C 0.43658(17) 0.30293(17) 0.31481(13) 0.0225(4) Uani 1 1 d . . .
C5 C 0.43348(17) 0.38684(17) 0.25990(13) 0.0242(4) Uani 1 1 d . . .
C6 C 0.37303(17) 0.47233(17) 0.31341(13) 0.0229(4) Uani 1 1 d . . .
C7 C 0.25188(17) 0.46705(17) 0.31694(13) 0.0228(4) Uani 1 1 d . . .
C8 C 0.24476(17) 0.56586(17) 0.38466(13) 0.0230(4) Uani 1 1 d . . .
C9 C 0.36218(17) 0.63364(17) 0.42267(13) 0.0230(4) Uani 1 1 d . . .
C10 C 0.41585(18) 0.75466(17) 0.48837(14) 0.0242(4) Uani 1 1 d . . .
C11 C 0.32129(18) 0.03448(18) 0.37270(15) 0.0292(5) Uani 1 1 d . . .
H11A H 0.3677 -0.0205 0.3513 0.035 Uiso 1 1 calc R . .
H11B H 0.2904 0.0268 0.4326 0.035 Uiso 1 1 calc R . .
C12 C 0.24961(18) 0.10295(17) 0.24782(15) 0.0286(5) Uani 1 1 d . . .
H12A H 0.1807 0.1335 0.2411 0.034 Uiso 1 1 calc R . .
H12B H 0.2720 0.0700 0.1858 0.034 Uiso 1 1 calc R . .
C13 C 0.2234(2) -0.18951(18) 0.18843(15) 0.0314(5) Uani 1 1 d . . .
C14 C 0.2626(2) -0.2663(2) 0.22308(15) 0.0355(5) Uani 1 1 d . . .
H14A H 0.2334 -0.2837 0.2781 0.043 Uiso 1 1 calc R . .
C15 C 0.3441(2) -0.3174(2) 0.17765(16) 0.0404(6) Uani 1 1 d . . .
H15A H 0.3694 -0.3704 0.2018 0.048 Uiso 1 1 calc R . .
C16 C 0.3897(2) -0.2936(2) 0.09803(17) 0.0447(6) Uani 1 1 d . . .
C17 C 0.3494(3) -0.2170(2) 0.06374(17) 0.0480(7) Uani 1 1 d . . .
H17A H 0.3795 -0.1993 0.0091 0.058 Uiso 1 1 calc R . .
C18 C 0.2663(2) -0.1658(2) 0.10745(16) 0.0410(6) Uani 1 1 d . . .
H18A H 0.2389 -0.1148 0.0822 0.049 Uiso 1 1 calc R . .
C19 C 0.4785(3) -0.3492(3) 0.0487(2) 0.0717(9) Uani 1 1 d . . .
H19A H 0.5066 -0.3906 0.0870 0.108 Uiso 1 1 calc R . .
H19B H 0.5496 -0.2895 0.0372 0.108 Uiso 1 1 calc R . .
H19C H 0.4372 -0.4039 -0.0105 0.108 Uiso 1 1 calc R . .
C20 C 0.56389(18) 0.44796(18) 0.24045(15) 0.0292(5) Uani 1 1 d . . .
H20A H 0.6150 0.4917 0.2991 0.044 Uiso 1 1 calc R . .
H20B H 0.5603 0.5010 0.2038 0.044 Uiso 1 1 calc R . .
H20C H 0.5999 0.3904 0.2059 0.044 Uiso 1 1 calc R . .
C21 C 0.35570(19) 0.31889(19) 0.16707(14) 0.0302(5) Uani 1 1 d . . .
H21A H 0.2719 0.2787 0.1783 0.045 Uiso 1 1 calc R . .
H21B H 0.3930 0.2622 0.1328 0.045 Uiso 1 1 calc R . .
H21C H 0.3525 0.3724 0.1308 0.045 Uiso 1 1 calc R . .
C22 C 0.12564(18) 0.38734(18) 0.27304(14) 0.0285(5) Uani 1 1 d . . .
H22A H 0.1087 0.3916 0.2095 0.034 Uiso 1 1 calc R . .
H22B H 0.1148 0.3062 0.2718 0.034 Uiso 1 1 calc R . .
C23 C 0.11214(17) 0.56182(17) 0.39369(14) 0.0255(4) Uani 1 1 d . . .
H23A H 0.0939 0.5768 0.4591 0.031 Uiso 1 1 calc R . .
H23B H 0.0908 0.6173 0.3658 0.031 Uiso 1 1 calc R . .
C24 C -0.11817(17) 0.46375(19) 0.22040(14) 0.0292(5) Uani 1 1 d . . .
C25 C -0.13032(18) 0.57369(19) 0.24564(15) 0.0319(5) Uani 1 1 d . . .
H25A H -0.1306 0.6120 0.3089 0.038 Uiso 1 1 calc R . .
C26 C -0.14196(19) 0.6266(2) 0.17776(16) 0.0366(5) Uani 1 1 d . . .
H26A H -0.1506 0.7015 0.1945 0.044 Uiso 1 1 calc R . .
C27 C -0.1411(2) 0.5705(2) 0.08449(16) 0.0399(6) Uani 1 1 d . . .
C28 C -0.1288(2) 0.4603(2) 0.06046(16) 0.0433(6) Uani 1 1 d . . .
H28A H -0.1277 0.4223 -0.0028 0.052 Uiso 1 1 calc R . .
C29 C -0.1182(2) 0.4058(2) 0.12729(15) 0.0369(5) Uani 1 1 d . . .
H29A H -0.1110 0.3303 0.1105 0.044 Uiso 1 1 calc R . .
C30 C -0.1533(3) 0.6292(3) 0.01095(19) 0.0591(8) Uani 1 1 d . . .
H30A H -0.0758 0.6906 0.0126 0.089 Uiso 1 1 calc R . .
H30B H -0.2204 0.6628 0.0225 0.089 Uiso 1 1 calc R . .
H30C H -0.1717 0.5724 -0.0500 0.089 Uiso 1 1 calc R . .
C31 C 0.30981(19) 0.79955(19) 0.52528(15) 0.0310(5) Uani 1 1 d . . .
H31A H 0.2604 0.7489 0.5597 0.046 Uiso 1 1 calc R . .
H31B H 0.2575 0.8001 0.4732 0.046 Uiso 1 1 calc R . .
H31C H 0.3441 0.8782 0.5663 0.046 Uiso 1 1 calc R . .
C32 C 0.49182(19) 0.83488(18) 0.43400(15) 0.0304(5) Uani 1 1 d . . .
H32A H 0.5592 0.8068 0.4097 0.046 Uiso 1 1 calc R . .
H32B H 0.5261 0.9135 0.4752 0.046 Uiso 1 1 calc R . .
H32C H 0.4385 0.8354 0.3825 0.046 Uiso 1 1 calc R . .
N1A N 0.1406(3) 0.2445(4) 0.5058(3) 0.0360(10) Uani 0.69 1 d PDU A 1
O1A O 0.3200(2) 0.3945(2) 0.54735(16) 0.0365(6) Uani 0.69 1 d PDU A 1
C1A C 0.2196(3) 0.3438(5) 0.5015(3) 0.0316(9) Uani 0.69 1 d PDU A 1
H1AA H 0.1962 0.3792 0.4587 0.038 Uiso 0.69 1 calc PR A 1
C2A C 0.0232(5) 0.1895(6) 0.4466(6) 0.0526(17) Uani 0.69 1 d PDU A 1
H2A1 H 0.0080 0.2437 0.4151 0.079 Uiso 0.69 1 calc PR A 1
H2A2 H -0.0439 0.1679 0.4847 0.079 Uiso 0.69 1 calc PR A 1
H2A3 H 0.0270 0.1201 0.4004 0.079 Uiso 0.69 1 calc PR A 1
C3A C 0.1690(4) 0.1820(4) 0.5675(3) 0.0491(10) Uani 0.69 1 d PDU A 1
H3A1 H 0.1006 0.1635 0.6052 0.074 Uiso 0.69 1 calc PR A 1
H3A2 H 0.2446 0.2300 0.6080 0.074 Uiso 0.69 1 calc PR A 1
H3A3 H 0.1808 0.1102 0.5308 0.074 Uiso 0.69 1 calc PR A 1
N1C N 0.1220(9) 0.2077(7) 0.4917(7) 0.034(3) Uiso 0.31 1 d PD B 2
O1C O 0.3035(6) 0.3401(6) 0.5653(4) 0.0512(19) Uiso 0.31 1 d PD B 2
C1C C 0.2123(9) 0.3070(8) 0.5089(8) 0.038(4) Uiso 0.31 1 d PD B 2
H1CA H 0.2058 0.3582 0.4740 0.046 Uiso 0.31 1 calc PR B 2
C2C C 0.0177(13) 0.1765(13) 0.4219(12) 0.057(5) Uiso 0.31 1 d PD B 2
H2C1 H 0.0245 0.2413 0.3957 0.085 Uiso 0.31 1 calc PR B 2
H2C2 H -0.0596 0.1588 0.4507 0.085 Uiso 0.31 1 calc PR B 2
H2C3 H 0.0181 0.1085 0.3725 0.085 Uiso 0.31 1 calc PR B 2
C3C C 0.1252(9) 0.1237(8) 0.5408(7) 0.052(3) Uiso 0.31 1 d PD B 2
H3C1 H 0.1035 0.0466 0.4968 0.078 Uiso 0.31 1 calc PR B 2
H3C2 H 0.0658 0.1236 0.5870 0.078 Uiso 0.31 1 calc PR B 2
H3C3 H 0.2083 0.1440 0.5717 0.078 Uiso 0.31 1 calc PR B 2
H2N H 0.521(2) 0.599(2) 0.3917(17) 0.047(7) Uiso 1 1 d . C 2
H1N H 0.572(2) 0.390(2) 0.4050(15) 0.025(6) Uiso 1 1 d . D 2
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 S1 O2 120.20(10) . .
O1 S1 N3 106.14(9) . .
O2 S1 N3 106.51(9) . .
O1 S1 C13 107.02(10) . .
O2 S1 C13 109.03(10) . .
N3 S1 C13 107.30(9) . .
O4 S2 O3 120.46(9) . .
O4 S2 N4 106.29(9) . .
O3 S2 N4 106.54(9) . .
O4 S2 C24 107.81(10) . .
O3 S2 C24 107.88(10) . .
N4 S2 C24 107.19(9) . .
C1 N1 C4 111.29(17) . .
C1 N1 H1N 128.8(17) . .
C4 N1 H1N 119.9(17) . .
C9 N2 C6 111.70(16) . .
C9 N2 H2N 124.3(16) . .
C6 N2 H2N 123.9(16) . .
C11 N3 C12 112.73(15) . .
C11 N3 S1 118.50(13) . .
C12 N3 S1 119.67(13) . .
C22 N4 C23 113.05(14) . .
C22 N4 S2 117.46(13) . .
C23 N4 S2 119.27(13) . .
N1 C1 C2 105.75(16) . .
N1 C1 C10 122.59(17) . 2_666
C2 C1 C10 131.49(17) . 2_666
C1 C2 C3 108.74(17) . .
C1 C2 C11 140.74(18) . .
C3 C2 C11 110.43(17) . .
C4 C3 C2 108.21(17) . .
C4 C3 C12 140.13(18) . .
C2 C3 C12 111.61(17) . .
C3 C4 N1 106.01(16) . .
C3 C4 C5 130.90(17) . .
N1 C4 C5 122.94(17) . .
C4 C5 C6 108.75(15) . .
C4 C5 C20 110.36(16) . .
C6 C5 C20 111.72(16) . .
C4 C5 C21 108.57(16) . .
C6 C5 C21 109.00(15) . .
C20 C5 C21 108.38(17) . .
C7 C6 N2 105.33(17) . .
C7 C6 C5 131.71(18) . .
N2 C6 C5 122.79(16) . .
C6 C7 C8 108.92(17) . .
C6 C7 C22 139.41(19) . .
C8 C7 C22 111.65(16) . .
C9 C8 C7 108.67(17) . .
C9 C8 C23 140.39(19) . .
C7 C8 C23 110.92(17) . .
C8 C9 N2 105.38(17) . .
C8 C9 C10 133.65(18) . .
N2 C9 C10 120.47(17) . .
C1 C10 C9 112.44(16) 2_666 .
C1 C10 C32 108.20(16) 2_666 .
C9 C10 C32 108.47(16) . .
C1 C10 C31 109.65(16) 2_666 .
C9 C10 C31 109.31(16) . .
C32 C10 C31 108.69(16) . .
N3 C11 C2 101.59(15) . .
N3 C11 H11A 111.5 . .
C2 C11 H11A 111.5 . .
N3 C11 H11B 111.5 . .
C2 C11 H11B 111.5 . .
H11A C11 H11B 109.3 . .
N3 C12 C3 100.66(15) . .
N3 C12 H12A 111.6 . .
C3 C12 H12A 111.6 . .
N3 C12 H12B 111.6 . .
C3 C12 H12B 111.6 . .
H12A C12 H12B 109.4 . .
C14 C13 C18 119.2(2) . .
C14 C13 S1 119.48(17) . .
C18 C13 S1 121.10(17) . .
C15 C14 C13 120.0(2) . .
C15 C14 H14A 120.0 . .
C13 C14 H14A 120.0 . .
C14 C15 C16 121.8(2) . .
C14 C15 H15A 119.1 . .
C16 C15 H15A 119.1 . .
C15 C16 C17 117.7(2) . .
C15 C16 C19 121.7(2) . .
C17 C16 C19 120.6(2) . .
C18 C17 C16 121.6(2) . .
C18 C17 H17A 119.2 . .
C16 C17 H17A 119.2 . .
C17 C18 C13 119.7(2) . .
C17 C18 H18A 120.2 . .
C13 C18 H18A 120.2 . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C5 C20 H20A 109.5 . .
C5 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C5 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C5 C21 H21A 109.5 . .
C5 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C5 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N4 C22 C7 99.75(15) . .
N4 C22 H22A 111.8 . .
C7 C22 H22A 111.8 . .
N4 C22 H22B 111.8 . .
C7 C22 H22B 111.8 . .
H22A C22 H22B 109.5 . .
N4 C23 C8 100.08(15) . .
N4 C23 H23A 111.8 . .
C8 C23 H23A 111.8 . .
N4 C23 H23B 111.8 . .
C8 C23 H23B 111.8 . .
H23A C23 H23B 109.5 . .
C25 C24 C29 121.0(2) . .
C25 C24 S2 119.10(16) . .
C29 C24 S2 119.88(18) . .
C26 C25 C24 119.4(2) . .
C26 C25 H25A 120.3 . .
C24 C25 H25A 120.3 . .
C25 C26 C27 120.4(2) . .
C25 C26 H26A 119.8 . .
C27 C26 H26A 119.8 . .
C28 C27 C26 119.4(2) . .
C28 C27 C30 120.6(2) . .
C26 C27 C30 120.0(2) . .
C29 C28 C27 120.9(2) . .
C29 C28 H28A 119.5 . .
C27 C28 H28A 119.5 . .
C28 C29 C24 118.9(2) . .
C28 C29 H29A 120.6 . .
C24 C29 H29A 120.6 . .
C27 C30 H30A 109.5 . .
C27 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C27 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C10 C31 H31A 109.5 . .
C10 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C10 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C10 C32 H32A 109.5 . .
C10 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C10 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C1A N1A C3A 121.0(4) . .
C1A N1A C2A 122.4(3) . .
C3A N1A C2A 116.6(4) . .
O1A C1A N1A 126.5(4) . .
O1A C1A H1AA 116.8 . .
N1A C1A H1AA 116.8 . .
C1C N1C C3C 120.4(7) . .
C1C N1C C2C 122.2(7) . .
C3C N1C C2C 117.4(7) . .
O1C C1C N1C 126.8(9) . .
O1C C1C H1CA 116.6 . .
N1C C1C H1CA 116.6 . .
N1C C2C H2C1 109.5 . .
N1C C2C H2C2 109.5 . .
H2C1 C2C H2C2 109.5 . .
N1C C2C H2C3 109.5 . .
H2C1 C2C H2C3 109.5 . .
H2C2 C2C H2C3 109.5 . .
N1C C3C H3C1 109.5 . .
N1C C3C H3C2 109.5 . .
H3C1 C3C H3C2 109.5 . .
N1C C3C H3C3 109.5 . .
H3C1 C3C H3C3 109.5 . .
H3C2 C3C H3C3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4262(16) .
S1 O2 1.4317(16) .
S1 N3 1.6270(17) .
S1 C13 1.766(2) .
S2 O4 1.4365(16) .
S2 O3 1.4422(16) .
S2 N4 1.6260(16) .
S2 C24 1.753(2) .
N1 C1 1.373(3) .
N1 C4 1.387(3) .
N1 H1N 0.77(2) .
N2 C9 1.387(2) .
N2 C6 1.391(3) .
N2 H2N 0.89(3) .
N3 C11 1.491(2) .
N3 C12 1.491(3) .
N4 C22 1.505(3) .
N4 C23 1.507(3) .
C1 C2 1.378(3) .
C1 C10 1.513(3) 2_666
C2 C3 1.408(3) .
C2 C11 1.494(3) .
C3 C4 1.371(3) .
C3 C12 1.503(3) .
C4 C5 1.511(3) .
C5 C6 1.520(3) .
C5 C20 1.529(3) .
C5 C21 1.533(3) .
C6 C7 1.369(3) .
C7 C8 1.416(3) .
C7 C22 1.508(3) .
C8 C9 1.373(3) .
C8 C23 1.511(3) .
C9 C10 1.522(3) .
C10 C1 1.513(3) 2_666
C10 C32 1.540(3) .
C10 C31 1.541(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.390(3) .
C13 C18 1.391(3) .
C14 C15 1.380(3) .
C14 H14A 0.9500 .
C15 C16 1.382(3) .
C15 H15A 0.9500 .
C16 C17 1.391(3) .
C16 C19 1.504(4) .
C17 C18 1.386(3) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.391(3) .
C24 C29 1.401(3) .
C25 C26 1.382(3) .
C25 H25A 0.9500 .
C26 C27 1.399(3) .
C26 H26A 0.9500 .
C27 C28 1.395(4) .
C27 C30 1.508(3) .
C28 C29 1.380(3) .
C28 H28A 0.9500 .
C29 H29A 0.9500 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
N1A C1A 1.323(6) .
N1A C3A 1.455(4) .
N1A C2A 1.466(5) .
O1A C1A 1.226(3) .
C1A H1AA 0.9500 .
C2A H2A1 0.9800 .
C2A H2A2 0.9800 .
C2A H2A3 0.9800 .
C3A H3A1 0.9800 .
C3A H3A2 0.9800 .
C3A H3A3 0.9800 .
N1C C1C 1.321(8) .
N1C C3C 1.449(7) .
N1C C2C 1.462(8) .
O1C C1C 1.226(7) .
C1C H1CA 0.9500 .
C2C H2C1 0.9800 .
C2C H2C2 0.9800 .
C2C H2C3 0.9800 .
C3C H3C1 0.9800 .
C3C H3C2 0.9800 .
C3C H3C3 0.9800 .
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 H2N O1A 0.89(3) 1.99(3) 2.829(3) 156(2) 2_666
N2 H2N O1C 0.89(3) 1.95(3) 2.838(6) 173(2) 2_666
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_4
O1 S1 N3 C11 49.81(17) . .
O2 S1 N3 C11 179.01(15) . .
C13 S1 N3 C11 -64.35(17) . .
O1 S1 N3 C12 -165.57(15) . .
O2 S1 N3 C12 -36.38(18) . .
C13 S1 N3 C12 80.27(17) . .
O4 S2 N4 C22 172.78(14) . .
O3 S2 N4 C22 43.15(16) . .
C24 S2 N4 C22 -72.14(16) . .
O4 S2 N4 C23 -44.36(16) . .
O3 S2 N4 C23 -173.99(14) . .
C24 S2 N4 C23 70.72(16) . .
C4 N1 C1 C2 0.0(2) . .
C4 N1 C1 C10 175.93(17) . 2_666
N1 C1 C2 C3 -0.4(2) . .
C10 C1 C2 C3 -175.8(2) 2_666 .
N1 C1 C2 C11 175.4(3) . .
C10 C1 C2 C11 0.0(4) 2_666 .
C1 C2 C3 C4 0.6(2) . .
C11 C2 C3 C4 -176.55(17) . .
C1 C2 C3 C12 178.49(17) . .
C11 C2 C3 C12 1.3(2) . .
C2 C3 C4 N1 -0.6(2) . .
C12 C3 C4 N1 -177.5(2) . .
C2 C3 C4 C5 -176.16(19) . .
C12 C3 C4 C5 6.9(4) . .
C1 N1 C4 C3 0.4(2) . .
C1 N1 C4 C5 176.38(17) . .
C3 C4 C5 C6 97.0(2) . .
N1 C4 C5 C6 -77.9(2) . .
C3 C4 C5 C20 -140.1(2) . .
N1 C4 C5 C20 44.9(3) . .
C3 C4 C5 C21 -21.5(3) . .
N1 C4 C5 C21 163.59(18) . .
C9 N2 C6 C7 0.6(2) . .
C9 N2 C6 C5 -175.26(16) . .
C4 C5 C6 C7 -85.6(2) . .
C20 C5 C6 C7 152.4(2) . .
C21 C5 C6 C7 32.6(3) . .
C4 C5 C6 N2 89.1(2) . .
C20 C5 C6 N2 -33.0(2) . .
C21 C5 C6 N2 -152.73(17) . .
N2 C6 C7 C8 -0.8(2) . .
C5 C6 C7 C8 174.55(18) . .
N2 C6 C7 C22 -178.5(2) . .
C5 C6 C7 C22 -3.2(4) . .
C6 C7 C8 C9 0.7(2) . .
C22 C7 C8 C9 179.14(16) . .
C6 C7 C8 C23 -177.89(16) . .
C22 C7 C8 C23 0.5(2) . .
C7 C8 C9 N2 -0.3(2) . .
C23 C8 C9 N2 177.6(2) . .
C7 C8 C9 C10 171.2(2) . .
C23 C8 C9 C10 -10.8(4) . .
C6 N2 C9 C8 -0.2(2) . .
C6 N2 C9 C10 -173.05(16) . .
C8 C9 C10 C1 129.9(2) . 2_666
N2 C9 C10 C1 -59.6(2) . 2_666
C8 C9 C10 C32 -110.5(2) . .
N2 C9 C10 C32 60.0(2) . .
C8 C9 C10 C31 7.8(3) . .
N2 C9 C10 C31 178.35(16) . .
C12 N3 C11 C2 17.6(2) . .
S1 N3 C11 C2 164.51(14) . .
C1 C2 C11 N3 173.2(2) . .
C3 C2 C11 N3 -11.1(2) . .
C11 N3 C12 C3 -16.7(2) . .
S1 N3 C12 C3 -163.19(14) . .
C4 C3 C12 N3 -174.1(2) . .
C2 C3 C12 N3 9.0(2) . .
O1 S1 C13 C14 -10.7(2) . .
O2 S1 C13 C14 -142.12(18) . .
N3 S1 C13 C14 102.90(18) . .
O1 S1 C13 C18 174.65(18) . .
O2 S1 C13 C18 43.2(2) . .
N3 S1 C13 C18 -71.8(2) . .
C18 C13 C14 C15 0.5(3) . .
S1 C13 C14 C15 -174.28(17) . .
C13 C14 C15 C16 0.7(4) . .
C14 C15 C16 C17 -0.9(4) . .
C14 C15 C16 C19 179.9(3) . .
C15 C16 C17 C18 0.0(4) . .
C19 C16 C17 C18 179.2(3) . .
C16 C17 C18 C13 1.1(4) . .
C14 C13 C18 C17 -1.4(3) . .
S1 C13 C18 C17 173.32(18) . .
C23 N4 C22 C7 21.28(19) . .
S2 N4 C22 C7 166.36(13) . .
C6 C7 C22 N4 165.0(2) . .
C8 C7 C22 N4 -12.7(2) . .
C22 N4 C23 C8 -21.1(2) . .
S2 N4 C23 C8 -165.46(13) . .
C9 C8 C23 N4 -166.0(2) . .
C7 C8 C23 N4 12.0(2) . .
O4 S2 C24 C25 25.83(19) . .
O3 S2 C24 C25 157.37(16) . .
N4 S2 C24 C25 -88.24(17) . .
O4 S2 C24 C29 -155.20(16) . .
O3 S2 C24 C29 -23.65(19) . .
N4 S2 C24 C29 90.74(18) . .
C29 C24 C25 C26 -0.3(3) . .
S2 C24 C25 C26 178.64(16) . .
C24 C25 C26 C27 -0.2(3) . .
C25 C26 C27 C28 0.2(3) . .
C25 C26 C27 C30 -179.7(2) . .
C26 C27 C28 C29 0.4(3) . .
C30 C27 C28 C29 -179.7(2) . .
C27 C28 C29 C24 -0.9(3) . .
C25 C24 C29 C28 0.9(3) . .
S2 C24 C29 C28 -178.06(17) . .
C3A N1A C1A O1A -1.5(8) . .
C2A N1A C1A O1A -178.9(6) . .
C3C N1C C1C O1C -1(2) . .
C2C N1C C1C O1C -179.4(15) . .
