#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/60/4116075.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_4116075
loop_
_publ_author_name
'Martin J. Deetz'
'Maoyu Shang'
'Bradley D. Smith'
_publ_section_title
;
 A Macrobicyclic Receptor with Versatile Recognition Properties:
 Simultaneous Binding of an Ion Pair and Selective Complexation of
 Dimethylsulfoxide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6201
_journal_page_last               6207
_journal_paper_doi               10.1021/ja994487r
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C47 H55 N4 O13.5 S1.5'
_chemical_formula_weight         940.04
_chemical_name_systematic
; 
(dicarboxamidedibenzocrown).2.0H2O.1.5Me2SO
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.880(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.531(3)
_cell_length_b                   14.1236(10)
_cell_length_c                   17.5199(17)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     9294.4(13)
_computing_cell_refinement       MADNES
_computing_data_collection       MADNES
_computing_data_reduction        'MADNES (Messerschmitt & Pflugrath, 1987)'
_computing_molecular_graphics    'ORTEP-III for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL-v5 (Siemens, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean 8.2/10.9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Enraf-Nonius FAST area-detector'
_diffrn_measurement_method       'Ellipsoid-mask fitting'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23008
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             3976
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment
;
 Hydron atoms from amide and water groups were refined with riding
thermal parameters, while the rest were idealized with riding models.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         8059
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0856
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1224P)²+38.0955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2462
_reflns_number_gt                5419
_reflns_number_total             8059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja994487r_2.cif
_cod_data_source_block           for_compound_1a.DMSO
_cod_original_formula_sum        'C47 H55 N4 O13.50 S1.50'
_cod_database_code               4116075
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20500(12) 0.6192(3) -0.3849(3) 0.0389(10) Uani 1 1 d . . .
O1 O 0.21264(11) 0.5871(2) -0.4440(2) 0.0615(10) Uani 1 1 d . . .
C2 C 0.19339(12) 0.5547(3) -0.3276(3) 0.0367(10) Uani 1 1 d . . .
C3 C 0.21464(12) 0.4781(3) -0.2990(3) 0.0407(11) Uani 1 1 d . . .
H3 H 0.2366 0.4707 -0.3133 0.049 Uiso 1 1 calc R . .
C4 C 0.20454(12) 0.4122(3) -0.2502(3) 0.0413(11) Uani 1 1 d . . .
H4 H 0.2198 0.3617 -0.2301 0.050 Uiso 1 1 calc R . .
C5 C 0.17169(12) 0.4211(3) -0.2310(3) 0.0354(10) Uani 1 1 d . . .
C6 C 0.15011(13) 0.4967(3) -0.2602(3) 0.0483(12) Uani 1 1 d . . .
H6 H 0.1276 0.5025 -0.2483 0.058 Uiso 1 1 calc R . .
C7 C 0.16122(13) 0.5640(3) -0.3066(3) 0.0495(12) Uani 1 1 d . . .
H7 H 0.1467 0.6166 -0.3241 0.059 Uiso 1 1 calc R . .
N1 N 0.15926(10) 0.3578(2) -0.1807(2) 0.0379(9) Uani 1 1 d . . .
H1N H 0.1403(14) 0.372(3) -0.167(3) 0.046 Uiso 1 1 d . . .
C8 C 0.17259(11) 0.2704(3) -0.1565(3) 0.0351(10) Uani 1 1 d . . .
O2 O 0.19645(9) 0.2321(2) -0.1798(2) 0.0463(8) Uani 1 1 d . . .
C9 C 0.15464(11) 0.2225(3) -0.0995(3) 0.0353(10) Uani 1 1 d . . .
C10 C 0.15630(13) 0.1241(3) -0.0937(3) 0.0408(10) Uani 1 1 d . . .
H10 H 0.1687 0.0893 -0.1249 0.049 Uiso 1 1 calc R . .
C11 C 0.13973(12) 0.0777(3) -0.0420(3) 0.0413(11) Uani 1 1 d . . .
H11 H 0.1410 0.0114 -0.0378 0.050 Uiso 1 1 calc R . .
C12 C 0.12128(13) 0.1291(3) 0.0034(3) 0.0423(11) Uani 1 1 d . . .
H12 H 0.1098 0.0973 0.0380 0.051 Uiso 1 1 calc R . .
C13 C 0.11964(12) 0.2273(3) -0.0017(3) 0.0370(10) Uani 1 1 d . . .
C14 C 0.13715(11) 0.2729(3) -0.0519(3) 0.0370(10) Uani 1 1 d . . .
H14 H 0.1372 0.3394 -0.0536 0.044 Uiso 1 1 calc R . .
C15 C 0.09896(13) 0.2800(3) 0.0478(3) 0.0421(11) Uani 1 1 d . . .
O3 O 0.09229(10) 0.2443(2) 0.1063(2) 0.0573(10) Uani 1 1 d . . .
N2 N 0.08824(11) 0.3682(3) 0.0232(2) 0.0422(10) Uani 1 1 d . . .
H2N H 0.0916(14) 0.381(4) -0.016(3) 0.051 Uiso 1 1 d . . .
C16 C 0.06815(12) 0.4337(3) 0.0573(3) 0.0404(10) Uani 1 1 d . . .
C17 C 0.06066(14) 0.4226(3) 0.1302(3) 0.0516(13) Uani 1 1 d . . .
H17 H 0.0696 0.3701 0.1614 0.062 Uiso 1 1 calc R . .
C18 C 0.03995(14) 0.4894(3) 0.1570(3) 0.0485(12) Uani 1 1 d . . .
H18 H 0.0343 0.4804 0.2059 0.058 Uiso 1 1 calc R . .
C19 C 0.02739(12) 0.5689(3) 0.1136(3) 0.0388(10) Uani 1 1 d . . .
C20 C 0.03598(13) 0.5799(3) 0.0410(3) 0.0448(11) Uani 1 1 d . . .
H20 H 0.0281 0.6341 0.0109 0.054 Uiso 1 1 calc R . .
C21 C 0.05566(13) 0.5137(3) 0.0127(3) 0.0443(11) Uani 1 1 d . . .
H21 H 0.0608 0.5219 -0.0368 0.053 Uiso 1 1 calc R . .
C22 C 0.00238(12) 0.6342(3) 0.1400(3) 0.0406(11) Uani 1 1 d . . .
O4 O -0.02301(8) 0.6021(2) 0.1645(2) 0.0528(9) Uani 1 1 d . . .
N3 N 0.00633(10) 0.7281(3) 0.1315(2) 0.0444(10) Uani 1 1 d . . .
C23 C -0.02231(14) 0.7914(4) 0.1401(4) 0.0640(16) Uani 1 1 d . . .
H23A H -0.0256 0.8395 0.0995 0.096 Uiso 1 1 calc R . .
H23B H -0.0163 0.8216 0.1911 0.096 Uiso 1 1 calc R . .
H23C H -0.0441 0.7555 0.1354 0.096 Uiso 1 1 calc R . .
C24 C 0.03971(12) 0.7705(3) 0.1258(3) 0.0383(10) Uani 1 1 d . . .
C25 C 0.06997(13) 0.7547(3) 0.1819(3) 0.0442(11) Uani 1 1 d . . .
H25 H 0.0694 0.7146 0.2244 0.053 Uiso 1 1 calc R . .
C26 C 0.10176(13) 0.7981(3) 0.1760(3) 0.0431(11) Uani 1 1 d . . .
H26 H 0.1226 0.7863 0.2144 0.052 Uiso 1 1 calc R . .
C27 C 0.10296(12) 0.8580(3) 0.1148(3) 0.0375(10) Uani 1 1 d . . .
C28 C 0.07199(12) 0.8733(3) 0.0568(2) 0.0360(10) Uani 1 1 d . . .
C29 C 0.04058(12) 0.8307(3) 0.0629(3) 0.0391(10) Uani 1 1 d . . .
H29 H 0.0197 0.8420 0.0247 0.047 Uiso 1 1 calc R . .
O5 O 0.07588(8) 0.9303(2) -0.00373(18) 0.0419(7) Uani 1 1 d . . .
C30 C 0.04638(12) 0.9352(3) -0.0693(3) 0.0420(11) Uani 1 1 d . . .
H30A H 0.0268 0.9699 -0.0549 0.050 Uiso 1 1 calc R . .
H30B H 0.0380 0.8712 -0.0855 0.050 Uiso 1 1 calc R . .
C31 C 0.05771(12) 0.9845(3) -0.1350(3) 0.0412(11) Uani 1 1 d . . .
H31A H 0.0369 0.9969 -0.1774 0.049 Uiso 1 1 calc R . .
H31B H 0.0687 1.0453 -0.1168 0.049 Uiso 1 1 calc R . .
O6 O 0.08228(8) 0.9277(2) -0.16323(17) 0.0393(7) Uani 1 1 d . . .
C32 C 0.09145(12) 0.9701(3) -0.2292(3) 0.0411(11) Uani 1 1 d . . .
H32A H 0.1020 1.0326 -0.2150 0.049 Uiso 1 1 calc R . .
H32B H 0.0700 0.9785 -0.2709 0.049 Uiso 1 1 calc R . .
C33 C 0.11756(12) 0.9085(3) -0.2579(3) 0.0425(11) Uani 1 1 d . . .
H33A H 0.1088 0.8431 -0.2638 0.051 Uiso 1 1 calc R . .
H33B H 0.1205 0.9309 -0.3090 0.051 Uiso 1 1 calc R . .
O7 O 0.15095(8) 0.9123(2) -0.20217(18) 0.0412(7) Uani 1 1 d . . .
C34 C 0.17737(11) 0.8552(3) -0.2159(2) 0.0331(9) Uani 1 1 d . . .
C35 C 0.20711(11) 0.8445(3) -0.1525(2) 0.0343(9) Uani 1 1 d . . .
O8 O 0.20533(8) 0.8954(2) -0.08737(18) 0.0437(8) Uani 1 1 d . . .
C36 C 0.23641(11) 0.8960(3) -0.0242(3) 0.0386(10) Uani 1 1 d . . .
H36A H 0.2564 0.9255 -0.0413 0.046 Uiso 1 1 calc R . .
H36B H 0.2431 0.8310 -0.0076 0.046 Uiso 1 1 calc R . .
C37 C 0.22802(12) 0.9501(3) 0.0417(3) 0.0419(11) Uani 1 1 d . . .
H37A H 0.2498 0.9602 0.0822 0.050 Uiso 1 1 calc R . .
H37B H 0.2182 1.0121 0.0232 0.050 Uiso 1 1 calc R . .
O9 O 0.20293(8) 0.8989(2) 0.07326(18) 0.0410(7) Uani 1 1 d . . .
C38 C 0.19344(12) 0.9453(3) 0.1369(3) 0.0418(11) Uani 1 1 d . . .
H38A H 0.1850 1.0094 0.1213 0.050 Uiso 1 1 calc R . .
H38B H 0.2143 0.9504 0.1805 0.050 Uiso 1 1 calc R . .
C39 C 0.16493(12) 0.8909(3) 0.1622(3) 0.0422(11) Uani 1 1 d . . .
H39A H 0.1711 0.8235 0.1670 0.051 Uiso 1 1 calc R . .
H39B H 0.1620 0.9137 0.2132 0.051 Uiso 1 1 calc R . .
O10 O 0.13269(8) 0.9044(2) 0.10424(18) 0.0431(8) Uani 1 1 d . . .
C40 C 0.17695(12) 0.8093(3) -0.2856(3) 0.0347(9) Uani 1 1 d . . .
H40 H 0.1573 0.8166 -0.3280 0.042 Uiso 1 1 calc R . .
C41 C 0.20553(11) 0.7522(3) -0.2934(2) 0.0316(9) Uani 1 1 d . . .
C42 C 0.23376(11) 0.7396(3) -0.2310(3) 0.0356(10) Uani 1 1 d . . .
H42 H 0.2527 0.6999 -0.2360 0.043 Uiso 1 1 calc R . .
C43 C 0.23434(11) 0.7851(3) -0.1609(3) 0.0373(10) Uani 1 1 d . . .
H43 H 0.2537 0.7754 -0.1182 0.045 Uiso 1 1 calc R . .
N4 N 0.20632(10) 0.7131(2) -0.3686(2) 0.0352(8) Uani 1 1 d . . .
C44 C 0.21852(13) 0.7773(3) -0.4230(3) 0.0402(10) Uani 1 1 d . . .
H44A H 0.2429 0.7963 -0.4009 0.060 Uiso 1 1 calc R . .
H44B H 0.2034 0.8329 -0.4318 0.060 Uiso 1 1 calc R . .
H44C H 0.2174 0.7450 -0.4724 0.060 Uiso 1 1 calc R . .
O11 O 0.09400(10) 0.4367(3) -0.1398(2) 0.0511(9) Uani 1 1 d . . .
H11A H 0.0976(14) 0.500(4) -0.141(3) 0.061 Uiso 1 1 d . . .
H11B H 0.0686(16) 0.427(4) -0.157(3) 0.061 Uiso 1 1 d . . .
O12 O 0.0336(3) 0.1249(9) 0.0883(7) 0.225(5) Uani 1 1 d D . .
H12A H 0.053(3) 0.174(8) 0.088(9) 0.270 Uiso 1 1 d D . .
H12B H 0.025(4) 0.136(12) 0.139(6) 0.270 Uiso 1 1 d D . .
S1 S 0.0000 0.2262(4) 0.2500 0.195(3) Uani 1 2 d S . .
C45 C 0.0289(3) 0.2988(7) 0.3073(6) 0.145(4) Uani 1 1 d . . .
H45A H 0.0167 0.3563 0.3169 0.217 Uiso 1 1 calc R . .
H45B H 0.0480 0.3146 0.2816 0.217 Uiso 1 1 calc R . .
H45C H 0.0388 0.2677 0.3568 0.217 Uiso 1 1 calc R . .
O13 O 0.0063(3) 0.1401(8) 0.2248(7) 0.103(4) Uani 0.50 1 d P . .
O14 O 0.10502(12) 0.6207(3) -0.1201(3) 0.1053(18) Uani 1 1 d DU . .
S2 S 0.14164(8) 0.67020(18) -0.0960(2) 0.1108(15) Uani 0.714(5) 1 d PDU A 1
C47 C 0.13753(18) 0.7704(4) -0.0516(4) 0.102(3) Uani 0.714(5) 1 d PDU A 1
H47A H 0.1310 0.8202 -0.0902 0.153 Uiso 0.714(5) 1 calc PR A 1
H47B H 0.1600 0.7861 -0.0164 0.153 Uiso 0.714(5) 1 calc PR A 1
H47C H 0.1192 0.7640 -0.0220 0.153 Uiso 0.714(5) 1 calc PR A 1
C48 C 0.1518(3) 0.6104(8) -0.0139(5) 0.325(12) Uani 0.714(5) 1 d PDU A 1
H48A H 0.1535 0.6533 0.0299 0.488 Uiso 0.714(5) 1 calc PR A 1
H48B H 0.1745 0.5788 -0.0101 0.488 Uiso 0.714(5) 1 calc PR A 1
H48C H 0.1335 0.5635 -0.0130 0.488 Uiso 0.714(5) 1 calc PR A 1
S3 S 0.11556(15) 0.6740(3) -0.0408(3) 0.073(2) Uani 0.286(5) 1 d PDU A 2
C49 C 0.13753(18) 0.7704(4) -0.0516(4) 0.102(3) Uani 0.29 1 d PDU A 2
H49A H 0.1457 0.8007 -0.0011 0.153 Uiso 0.286(5) 1 calc PR A 2
H49B H 0.1220 0.8133 -0.0869 0.153 Uiso 0.286(5) 1 calc PR A 2
H49C H 0.1578 0.7542 -0.0733 0.153 Uiso 0.286(5) 1 calc PR A 2
C50 C 0.1518(3) 0.6104(8) -0.0139(5) 0.325(12) Uani 0.29 1 d PDU A 2
H50A H 0.1612 0.6179 0.0419 0.488 Uiso 0.286(5) 1 calc PR A 2
H50B H 0.1694 0.6313 -0.0422 0.488 Uiso 0.286(5) 1 calc PR A 2
H50C H 0.1462 0.5442 -0.0255 0.488 Uiso 0.286(5) 1 calc PR A 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'
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 C1 N4 122.5(4) . .
O1 C1 C2 120.4(4) . .
N4 C1 C2 117.1(4) . .
C7 C2 C3 118.3(4) . .
C7 C2 C1 122.9(4) . .
C3 C2 C1 118.6(4) . .
C4 C3 C2 121.8(4) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C5 119.3(4) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C5 C4 119.2(4) . .
C6 C5 N1 117.5(4) . .
C4 C5 N1 123.3(4) . .
C7 C6 C5 120.7(4) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C2 C7 C6 120.6(4) . .
C2 C7 H7 119.7 . .
C6 C7 H7 119.7 . .
C8 N1 C5 127.5(4) . .
C8 N1 H1N 115(3) . .
C5 N1 H1N 117(3) . .
O2 C8 N1 123.9(4) . .
O2 C8 C9 121.4(4) . .
N1 C8 C9 114.7(4) . .
C14 C9 C10 119.4(4) . .
C14 C9 C8 122.1(4) . .
C10 C9 C8 118.6(4) . .
C11 C10 C9 120.0(4) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C12 C11 C10 120.0(4) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.4(4) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 119.0(4) . .
C14 C13 C15 122.3(4) . .
C12 C13 C15 118.7(4) . .
C9 C14 C13 121.2(4) . .
C9 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
O3 C15 N2 122.8(4) . .
O3 C15 C13 121.3(4) . .
N2 C15 C13 115.9(4) . .
C15 N2 C16 128.5(4) . .
C15 N2 H2N 114(4) . .
C16 N2 H2N 117(4) . .
C17 C16 C21 119.5(4) . .
C17 C16 N2 124.2(4) . .
C21 C16 N2 116.4(4) . .
C16 C17 C18 119.5(4) . .
C16 C17 H17 120.3 . .
C18 C17 H17 120.3 . .
C17 C18 C19 121.7(4) . .
C17 C18 H18 119.2 . .
C19 C18 H18 119.2 . .
C18 C19 C20 117.9(4) . .
C18 C19 C22 120.4(4) . .
C20 C19 C22 121.3(4) . .
C21 C20 C19 121.3(4) . .
C21 C20 H20 119.4 . .
C19 C20 H20 119.4 . .
C20 C21 C16 120.1(4) . .
C20 C21 H21 119.9 . .
C16 C21 H21 119.9 . .
O4 C22 N3 121.0(4) . .
O4 C22 C19 120.0(4) . .
N3 C22 C19 118.7(4) . .
C22 N3 C24 122.7(4) . .
C22 N3 C23 119.2(4) . .
C24 N3 C23 117.4(4) . .
N3 C23 H23A 109.5 . .
N3 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
N3 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C25 C24 C29 120.0(4) . .
C25 C24 N3 120.9(4) . .
C29 C24 N3 119.1(4) . .
C24 C25 C26 119.9(4) . .
C24 C25 H25 120.0 . .
C26 C25 H25 120.0 . .
C27 C26 C25 120.7(5) . .
C27 C26 H26 119.6 . .
C25 C26 H26 119.6 . .
O10 C27 C26 125.1(4) . .
O10 C27 C28 115.6(4) . .
C26 C27 C28 119.3(4) . .
O5 C28 C29 124.6(4) . .
O5 C28 C27 115.5(4) . .
C29 C28 C27 119.8(4) . .
C28 C29 C24 120.2(4) . .
C28 C29 H29 119.9 . .
C24 C29 H29 119.9 . .
C28 O5 C30 116.6(3) . .
O5 C30 C31 109.1(4) . .
O5 C30 H30A 109.9 . .
C31 C30 H30A 109.9 . .
O5 C30 H30B 109.9 . .
C31 C30 H30B 109.9 . .
H30A C30 H30B 108.3 . .
O6 C31 C30 109.8(3) . .
O6 C31 H31A 109.7 . .
C30 C31 H31A 109.7 . .
O6 C31 H31B 109.7 . .
C30 C31 H31B 109.7 . .
H31A C31 H31B 108.2 . .
C31 O6 C32 110.8(3) . .
O6 C32 C33 109.7(4) . .
O6 C32 H32A 109.7 . .
C33 C32 H32A 109.7 . .
O6 C32 H32B 109.7 . .
C33 C32 H32B 109.7 . .
H32A C32 H32B 108.2 . .
O7 C33 C32 108.5(4) . .
O7 C33 H33A 110.0 . .
C32 C33 H33A 110.0 . .
O7 C33 H33B 110.0 . .
C32 C33 H33B 110.0 . .
H33A C33 H33B 108.4 . .
C34 O7 C33 116.8(3) . .
O7 C34 C40 124.9(4) . .
O7 C34 C35 115.5(4) . .
C40 C34 C35 119.5(4) . .
O8 C35 C43 126.3(4) . .
O8 C35 C34 114.7(4) . .
C43 C35 C34 119.0(4) . .
C35 O8 C36 117.3(3) . .
O8 C36 C37 108.3(3) . .
O8 C36 H36A 110.0 . .
C37 C36 H36A 110.0 . .
O8 C36 H36B 110.0 . .
C37 C36 H36B 110.0 . .
H36A C36 H36B 108.4 . .
O9 C37 C36 109.2(3) . .
O9 C37 H37A 109.8 . .
C36 C37 H37A 109.8 . .
O9 C37 H37B 109.8 . .
C36 C37 H37B 109.8 . .
H37A C37 H37B 108.3 . .
C38 O9 C37 113.1(3) . .
O9 C38 C39 109.6(4) . .
O9 C38 H38A 109.8 . .
C39 C38 H38A 109.8 . .
O9 C38 H38B 109.8 . .
C39 C38 H38B 109.8 . .
H38A C38 H38B 108.2 . .
O10 C39 C38 107.5(4) . .
O10 C39 H39A 110.2 . .
C38 C39 H39A 110.2 . .
O10 C39 H39B 110.2 . .
C38 C39 H39B 110.2 . .
H39A C39 H39B 108.5 . .
C27 O10 C39 117.4(3) . .
C34 C40 C41 120.2(4) . .
C34 C40 H40 119.9 . .
C41 C40 H40 119.9 . .
C42 C41 C40 120.0(4) . .
C42 C41 N4 120.4(4) . .
C40 C41 N4 119.3(4) . .
C41 C42 C43 120.0(4) . .
C41 C42 H42 120.0 . .
C43 C42 H42 120.0 . .
C35 C43 C42 121.1(4) . .
C35 C43 H43 119.4 . .
C42 C43 H43 119.4 . .
C1 N4 C41 124.3(3) . .
C1 N4 C44 117.9(3) . .
C41 N4 C44 115.8(3) . .
N4 C44 H44A 109.5 . .
N4 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
N4 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
H11A O11 H11B 107(5) . .
H12A O12 H12B 107(3) . .
O13 S1 O13 48.5(9) . 2
O13 S1 C45 127.7(7) . .
O13 S1 C45 120.4(7) 2 .
O13 S1 C45 120.4(7) . 2
O13 S1 C45 127.7(7) 2 2
C45 S1 C45 104.4(7) . 2
S1 C45 H45A 109.5 . .
S1 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
S1 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
O13 O13 S1 65.7(5) 2 .
S2 O14 S3 59.7(3) . .
O14 S2 C48 91.8(5) . .
O14 S2 C47 109.9(3) . .
C48 S2 C47 93.3(5) . .
S2 C47 H47A 109.5 . .
S2 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
S2 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
S2 C48 H48A 109.5 . .
S2 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
S2 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
O14 S3 C49 109.9(3) . .
O14 S3 C50 91.6(5) . .
C49 S3 C50 93.5(5) . .
S3 C49 H49A 109.5 . .
S3 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
S3 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
S3 C50 H50A 109.5 . .
S3 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
S3 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.224(5) .
C1 N4 1.356(5) .
C1 C2 1.497(6) .
C2 C7 1.375(6) .
C2 C3 1.382(6) .
C3 C4 1.378(6) .
C3 H3 0.9400 .
C4 C5 1.386(6) .
C4 H4 0.9400 .
C5 C6 1.380(6) .
C5 N1 1.412(5) .
C6 C7 1.379(6) .
C6 H6 0.9400 .
C7 H7 0.9400 .
N1 C8 1.368(5) .
N1 H1N 0.84(5) .
C8 O2 1.213(5) .
C8 C9 1.496(6) .
C9 C14 1.382(6) .
C9 C10 1.394(6) .
C10 C11 1.384(6) .
C10 H10 0.9400 .
C11 C12 1.385(6) .
C11 H11 0.9400 .
C12 C13 1.392(6) .
C12 H12 0.9400 .
C13 C14 1.380(6) .
C13 C15 1.499(6) .
C14 H14 0.9400 .
C15 O3 1.220(5) .
C15 N2 1.352(6) .
N2 C16 1.420(6) .
N2 H2N 0.75(5) .
C16 C17 1.379(7) .
C16 C21 1.397(6) .
C17 C18 1.383(7) .
C17 H17 0.9400 .
C18 C19 1.382(6) .
C18 H18 0.9400 .
C19 C20 1.392(6) .
C19 C22 1.480(6) .
C20 C21 1.365(6) .
C20 H20 0.9400 .
C21 H21 0.9400 .
C22 O4 1.238(5) .
C22 N3 1.347(6) .
N3 C24 1.443(6) .
N3 C23 1.454(6) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 H23C 0.9700 .
C24 C25 1.365(7) .
C24 C29 1.398(6) .
C25 C26 1.394(7) .
C25 H25 0.9400 .
C26 C27 1.376(6) .
C26 H26 0.9400 .
C27 O10 1.368(5) .
C27 C28 1.401(6) .
C28 O5 1.366(5) .
C28 C29 1.378(6) .
C29 H29 0.9400 .
O5 C30 1.426(5) .
C30 C31 1.492(6) .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C31 O6 1.412(5) .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
O6 C32 1.415(5) .
C32 C33 1.499(6) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C33 O7 1.433(5) .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
O7 C34 1.362(5) .
C34 C40 1.379(6) .
C34 C35 1.415(6) .
C35 O8 1.363(5) .
C35 C43 1.376(6) .
O8 C36 1.439(5) .
C36 C37 1.478(6) .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C37 O9 1.415(5) .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
O9 C38 1.410(5) .
C38 C39 1.487(6) .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C39 O10 1.431(5) .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C40 C41 1.397(6) .
C40 H40 0.9400 .
C41 C42 1.370(6) .
C41 N4 1.434(5) .
C42 C43 1.383(6) .
C42 H42 0.9400 .
C43 H43 0.9400 .
N4 C44 1.467(5) .
C44 H44A 0.9700 .
C44 H44B 0.9700 .
C44 H44C 0.9700 .
O11 H11A 0.91(6) .
O11 H11B 0.97(6) .
O12 H12A 1.02(2) .
O12 H12B 1.02(2) .
S1 O13 1.333(11) .
S1 O13 1.333(11) 2
S1 C45 1.675(9) .
S1 C45 1.675(9) 2
C45 H45A 0.9700 .
C45 H45B 0.9700 .
C45 H45C 0.9700 .
O13 O13 1.10(2) 2
O14 S2 1.547(5) .
O14 S3 1.552(5) .
S2 C48 1.639(6) .
S2 C47 1.639(6) .
C47 H47A 0.9700 .
C47 H47B 0.9700 .
C47 H47C 0.9700 .
C48 H48A 0.9700 .
C48 H48B 0.9700 .
C48 H48C 0.9700 .
S3 C49 1.637(6) .
S3 C50 1.640(6) .
C49 H49A 0.97 .
C49 H49B 0.97 .
C49 H49C 0.97 .
C50 H50A 0.97 .
C50 H50B 0.97 .
C50 H50C 0.97 .
