#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:20:33 +0100 (vie 25 de mar de 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051927.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_7051927
loop_
_publ_author_name
'Bhogala, Balakrishna R.'
'Nangia, Ashwini'
_publ_section_title
;
 Ternary and quaternary co-crystals of
 1,3-cis,5-cis-cyclohexanetricarboxylic acid and
 4,4′-bipyridines
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              800
_journal_paper_doi               10.1039/b800293b
_journal_volume                  32
_journal_year                    2008
_chemical_formula_moiety         2(C9H12O6),2(C12H12N2),(C14H16N2),(C7H8O)
_chemical_formula_sum            'C63 H72 N6 O13'
_chemical_formula_weight         1121.27
_chemical_name_systematic
;
cis,cis-1,3,5-cyclohexanetricarboxylic acid
- 1,2-bis(4-pyridyl)ethane - 1,4-bis(4-pyridyl)butane - benzylalcohol
;
_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                94.300(2)
_cell_angle_beta                 91.509(2)
_cell_angle_gamma                94.623(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7311(6)
_cell_length_b                   18.4298(18)
_cell_length_c                   27.577(3)
_cell_measurement_reflns_used    3377
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.58
_cell_volume                     2893.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            22418
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         11350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1612
_refine_ls_R_factor_gt           0.1128
_refine_ls_shift/su_max          2.010
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1648P)²+5.3660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2937
_refine_ls_wR_factor_ref         0.3377
_reflns_number_gt                6965
_reflns_number_total             11350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800293b.txt
_cod_data_source_block           5g
_cod_database_code               7051927
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
O1 O 0.0831(5) 0.88038(17) 1.01640(10) 0.0387(7) Uani 1 1 d . . .
H1AA H -0.0150 0.8957 1.0359 0.058 Uiso 1 1 calc R . .
O2 O -0.1940(5) 0.89833(19) 0.96150(12) 0.0470(8) Uani 1 1 d . . .
O6 O 0.4361(6) 0.64505(17) 0.95167(12) 0.0503(9) Uani 1 1 d . . .
N2 N 0.7913(6) 0.92440(19) 0.08361(13) 0.0343(8) Uani 1 1 d . . .
N1 N -0.3211(6) 1.0665(2) 0.42236(14) 0.0395(9) Uani 1 1 d . . .
C1 C -0.0028(7) 0.8796(2) 0.97142(15) 0.0297(9) Uani 1 1 d . . .
O5 O 0.6715(7) 0.66128(18) 0.88993(15) 0.0691(13) Uani 1 1 d . . .
H5AA H 0.7166 0.6212 0.8974 0.104 Uiso 1 1 calc R . .
C24 C 0.0783(7) 0.9613(2) 0.31161(17) 0.0369(10) Uani 1 1 d . . .
H24A H -0.0236 0.9202 0.2953 0.044 Uiso 1 1 calc R . .
H24B H 0.2142 0.9406 0.3267 0.044 Uiso 1 1 calc R . .
C7 C 0.4171(7) 0.7525(2) 0.90815(14) 0.0301(9) Uani 1 1 d . . .
H7 H 0.554(8) 0.790(2) 0.9098(15) 0.036 Uiso 1 1 calc . . .
C21 C -0.0560(7) 0.9986(2) 0.35093(17) 0.0351(10) Uani 1 1 d . . .
C27 C 0.3755(8) 1.0223(2) 0.19487(16) 0.0398(11) Uani 1 1 d . . .
H27A H 0.2365 1.0410 0.1796 0.048 Uiso 1 1 calc R . .
H27B H 0.4722 1.0646 0.2110 0.048 Uiso 1 1 calc R . .
C29 C 0.4542(7) 0.9854(2) 0.10668(16) 0.0368(10) Uani 1 1 d . . .
H29 H 0.3163 1.0064 0.0967 0.044 Uiso 1 1 calc R . .
C9 C 0.2460(7) 0.7779(2) 0.94574(13) 0.0272(8) Uani 1 1 d . . .
H9A H 0.3223 0.7818 0.9786 0.033 Uiso 1 1 calc R . .
H9B H 0.1083 0.7418 0.9455 0.033 Uiso 1 1 calc R . .
C8 C 0.5067(8) 0.6810(2) 0.91950(17) 0.0400(11) Uani 1 1 d . . .
C20 C 0.0112(7) 1.0038(2) 0.39961(16) 0.0368(10) Uani 1 1 d . . .
H20 H 0.1507 0.9837 0.4096 0.044 Uiso 1 1 calc R . .
C2 C 0.1664(7) 0.8525(2) 0.93436(14) 0.0300(9) Uani 1 1 d . . .
H2 H 0.308(8) 0.888(2) 0.9366(15) 0.036 Uiso 1 1 calc . . .
C32 C 0.7214(8) 0.9551(3) 0.16745(17) 0.0424(11) Uani 1 1 d . . .
H32 H 0.7710 0.9541 0.2005 0.051 Uiso 1 1 calc R . .
C19 C -0.1231(7) 1.0378(2) 0.43387(17) 0.0396(10) Uani 1 1 d . . .
H19 H -0.0720 1.0409 0.4671 0.048 Uiso 1 1 calc R . .
C30 C 0.5920(7) 0.9538(2) 0.07213(17) 0.0369(10) Uani 1 1 d . . .
H30 H 0.5440 0.9527 0.0388 0.044 Uiso 1 1 calc R . .
C28 C 0.5151(7) 0.9870(2) 0.15573(16) 0.0372(10) Uani 1 1 d . . .
C31 C 0.8514(7) 0.9255(2) 0.13117(17) 0.0396(10) Uani 1 1 d . . .
H31 H 0.9912 0.9047 0.1401 0.047 Uiso 1 1 calc R . .
C25 C 0.1659(6) 1.0118(2) 0.27350(15) 0.0296(9) Uani 1 1 d . . .
H25A H 0.0310 1.0337 0.2590 0.035 Uiso 1 1 calc R . .
H25B H 0.2728 1.0519 0.2895 0.035 Uiso 1 1 calc R . .
C23 C -0.3854(7) 1.0627(3) 0.37549(18) 0.0436(11) Uani 1 1 d . . .
H23 H -0.5250 1.0837 0.3666 0.052 Uiso 1 1 calc R . .
C26 C 0.2940(7) 0.9718(2) 0.23333(16) 0.0332(9) Uani 1 1 d . . .
H26A H 0.4313 0.9509 0.2477 0.040 Uiso 1 1 calc R . .
H26B H 0.1884 0.9310 0.2178 0.040 Uiso 1 1 calc R . .
C22 C -0.2608(8) 1.0302(3) 0.33917(19) 0.0463(12) Uani 1 1 d . . .
H22 H -0.3142 1.0292 0.3062 0.056 Uiso 1 1 calc R . .
C6 C 0.3098(8) 0.7484(3) 0.85671(15) 0.0436(11) Uani 1 1 d . . .
H6A H 0.1739 0.7114 0.8537 0.052 Uiso 1 1 calc R . .
H6B H 0.4267 0.7332 0.8330 0.052 Uiso 1 1 calc R . .
C3 C 0.0633(8) 0.8507(3) 0.88320(16) 0.0476(13) Uani 1 1 d . . .
H3A H 0.0263 0.9006 0.8763 0.057 Uiso 1 1 calc R . .
H3B H -0.0848 0.8189 0.8807 0.057 Uiso 1 1 calc R . .
C4 C 0.2308(9) 0.8226(3) 0.84530(16) 0.0498(13) Uani 1 1 d . . .
H4 H 0.373(10) 0.858(3) 0.8462(19) 0.060 Uiso 1 1 calc . . .
C5 C 0.1177(12) 0.8185(5) 0.7942(2) 0.087(3) Uani 1 1 d . . .
O11 O 0.3926(5) 0.11627(17) 0.48968(11) 0.0416(8) Uani 1 1 d . . .
H11A H 0.4875 0.0982 0.4705 0.062 Uiso 1 1 calc R . .
O10 O 0.0744(6) 0.37233(17) 0.54329(13) 0.0496(9) Uani 1 1 d . . .
C15 C 0.2593(7) 0.2371(2) 0.55384(13) 0.0281(8) Uani 1 1 d . . .
H15A H 0.3985 0.2720 0.5514 0.034 Uiso 1 1 calc R . .
H15B H 0.1786 0.2295 0.5215 0.034 Uiso 1 1 calc R . .
C16 C 0.3364(7) 0.1641(2) 0.56938(15) 0.0345(10) Uani 1 1 d . . .
H16 H 0.193(8) 0.130(2) 0.5704(16) 0.041 Uiso 1 1 calc . . .
O12 O 0.6963(6) 0.1199(2) 0.54222(16) 0.0639(11) Uani 1 1 d . . .
O7 O 0.3952(7) 0.1814(2) 0.73546(14) 0.0613(17) Uani 1.000(15) 1 d . . .
H7AA H 0.4688 0.1966 0.7615 0.092 Uiso 0.70(12) 1 calc PR . .
C17 C 0.4957(7) 0.1314(2) 0.53297(17) 0.0378(10) Uani 1 1 d . . .
C14 C 0.0049(9) 0.3384(2) 0.57638(19) 0.0516(13) Uani 1 1 d . . .
C13 C 0.0950(8) 0.2686(2) 0.59078(15) 0.0392(11) Uani 1 1 d . . .
H13 H -0.043(8) 0.232(3) 0.5925(17) 0.047 Uiso 1 1 calc . . .
O9 O -0.1632(10) 0.3591(2) 0.6046(2) 0.108(2) Uani 1 1 d . . .
H9AA H -0.2097 0.3982 0.5956 0.162 Uiso 1 1 calc R . .
C18 C 0.4492(9) 0.1744(4) 0.62058(19) 0.0629(17) Uani 1 1 d . . .
H18A H 0.5984 0.2053 0.6198 0.075 Uiso 1 1 calc R . .
H18B H 0.4858 0.1263 0.6311 0.075 Uiso 1 1 calc R . .
C12 C 0.2098(11) 0.2806(3) 0.64103(17) 0.0649(17) Uani 1 1 d . . .
H12A H 0.0970 0.2999 0.6643 0.078 Uiso 1 1 calc R . .
H12B H 0.3459 0.3172 0.6406 0.078 Uiso 1 1 calc R . .
C11 C 0.2904(11) 0.2100(4) 0.65760(18) 0.070(2) Uani 1 1 d . . .
H11 H 0.149(11) 0.175(3) 0.661(2) 0.084 Uiso 1 1 calc . . .
O8 O 0.4756(12) 0.2972(3) 0.72328(19) 0.042(2) Uani 0.531(12) 1 d P . .
C10 C 0.4123(16) 0.2271(6) 0.7074(2) 0.116(4) Uani 1 1 d . . .
N3 N 0.3083(7) 0.7807(2) 0.18765(16) 0.0484(10) Uani 1 1 d . . .
N4 N 0.1621(7) 0.4611(2) 0.08816(16) 0.0508(11) Uani 1 1 d . . .
C43 C 0.2638(9) 0.5006(3) 0.05483(19) 0.0523(13) Uani 1 1 d . . .
H43 H 0.4039 0.4849 0.0414 0.063 Uiso 1 1 calc R . .
C35 C -0.0228(8) 0.7338(2) 0.11462(16) 0.0372(10) Uani 1 1 d . . .
C34 C -0.0697(9) 0.7215(3) 0.1621(2) 0.0520(13) Uani 1 1 d . . .
H34 H -0.2133 0.6968 0.1705 0.062 Uiso 1 1 calc R . .
C40 C -0.0197(10) 0.5863(2) 0.05747(18) 0.0512(13) Uani 1 1 d . . .
C36 C 0.1907(8) 0.7693(2) 0.10586(18) 0.0445(11) Uani 1 1 d . . .
H36 H 0.2288 0.7784 0.0734 0.053 Uiso 1 1 calc R . .
C37 C 0.3465(8) 0.7913(3) 0.14247(19) 0.0470(12) Uani 1 1 d . . .
H37 H 0.4915 0.8159 0.1348 0.056 Uiso 1 1 calc R . .
C44 C 0.1812(10) 0.5610(3) 0.03902(19) 0.0551(14) Uani 1 1 d . . .
H44 H 0.2621 0.5863 0.0149 0.066 Uiso 1 1 calc R . .
C42 C -0.0337(9) 0.4849(3) 0.1070(2) 0.0565(15) Uani 1 1 d . . .
H42 H -0.1102 0.4579 0.1309 0.068 Uiso 1 1 calc R . .
C41 C -0.1283(10) 0.5466(3) 0.0931(2) 0.0596(15) Uani 1 1 d . . .
H41 H -0.2662 0.5622 0.1076 0.071 Uiso 1 1 calc R . .
C38 C -0.1991(10) 0.7065(3) 0.0743(2) 0.0610(15) Uani 1 1 d . . .
H38A H -0.3414 0.6849 0.0891 0.073 Uiso 1 1 calc R . .
H38B H -0.2443 0.7488 0.0572 0.073 Uiso 1 1 calc R . .
C33 C 0.1069(11) 0.7475(3) 0.19853(17) 0.0581(15) Uani 1 1 d . . .
H33 H 0.0772 0.7405 0.2317 0.070 Uiso 1 1 calc R . .
C39 C -0.1177(12) 0.6523(3) 0.0385(2) 0.0650(16) Uani 1 1 d . . .
H39A H 0.0045 0.6772 0.0194 0.078 Uiso 1 1 calc R . .
H39B H -0.2505 0.6353 0.0157 0.078 Uiso 1 1 calc R . .
C51 C 0.4847(8) 0.2522(2) 0.38896(15) 0.0351(10) Uani 1 1 d . . .
N6A N 0.2337(17) 0.2163(4) 0.3016(3) 0.115(4) Uani 1.000(18) 1 d . . .
N5 N 0.3526(9) 0.5222(2) 0.4144(2) 0.0749(16) Uani 1 1 d . . .
C50 C 0.6261(8) 0.2708(3) 0.43561(17) 0.0466(12) Uani 1 1 d . . .
H50A H 0.5181 0.2701 0.4630 0.056 Uiso 1 1 calc R . .
H50B H 0.7341 0.2323 0.4396 0.056 Uiso 1 1 calc R . .
C52 C 0.2631(9) 0.2170(3) 0.3884(2) 0.0532(13) Uani 1 1 d . . .
H52 H 0.1923 0.2047 0.4178 0.064 Uiso 1 1 calc R . .
C55 C 0.5709(10) 0.2688(3) 0.34456(18) 0.0536(13) Uani 1 1 d . . .
H55 H 0.7221 0.2934 0.3427 0.064 Uiso 1 1 calc R . .
C46 C 0.4254(10) 0.4192(3) 0.4567(2) 0.0624(16) Uani 1 1 d . . .
H46 H 0.3789 0.3876 0.4810 0.075 Uiso 1 1 calc R . .
C47 C 0.6210(9) 0.4063(3) 0.4304(2) 0.0555(14) Uani 1 1 d . . .
C48 C 0.6729(11) 0.4535(3) 0.3947(2) 0.0707(19) Uani 1 1 d . . .
H48 H 0.8018 0.4462 0.3744 0.085 Uiso 1 1 calc R . .
C53 C 0.1451(11) 0.1998(3) 0.3434(4) 0.080(2) Uani 1 1 d . . .
H53 H -0.0068 0.1749 0.3429 0.095 Uiso 1 1 calc R . .
C45 C 0.2971(10) 0.4766(3) 0.4484(2) 0.0692(19) Uani 1 1 d . . .
H45 H 0.1644 0.4843 0.4675 0.083 Uiso 1 1 calc R . .
C49 C 0.7666(9) 0.3432(3) 0.4389(2) 0.0633(16) Uani 1 1 d . . .
H49A H 0.8904 0.3418 0.4146 0.076 Uiso 1 1 calc R . .
H49B H 0.8445 0.3517 0.4715 0.076 Uiso 1 1 calc R . .
C54 C 0.439(2) 0.2497(5) 0.3041(2) 0.103(3) Uani 1 1 d . . .
H54 H 0.5045 0.2622 0.2742 0.123 Uiso 1 1 calc R . .
C56 C 0.5407(11) 0.5100(3) 0.3884(3) 0.077(2) Uani 1 1 d . . .
H56 H 0.5840 0.5425 0.3644 0.093 Uiso 1 1 calc R . .
O13 O 0.4701(12) 0.4028(4) 0.8048(2) 0.127(2) Uani 1 1 d . . .
H13A H 0.5213 0.3743 0.7831 0.190 Uiso 1 1 calc R . .
C58 C 0.1669(16) 0.4547(4) 0.7333(3) 0.085(2) Uani 1 1 d . . .
C62 C -0.0574(17) 0.5535(5) 0.7133(3) 0.097(3) Uani 1 1 d . . .
C57 C 0.517(2) 0.4710(6) 0.7941(3) 0.103(3) Uani 1 1 d . . .
C64 C 0.285(2) 0.5701(6) 0.7724(3) 0.103(3) Uani 1 1 d . . .
C63 C 0.279(2) 0.5061(5) 0.7614(4) 0.151(6) Uani 1 1 d . . .
C59 C -0.022(2) 0.4824(7) 0.7071(4) 0.133(4) Uani 1 1 d . . .
O16 O 0.035(3) 0.6171(10) 0.7016(6) 0.322(8) Uani 1 1 d . . .
C65 C 0.083(4) 0.6019(7) 0.7462(5) 0.172(7) Uani 1 1 d . . .
O15 O 0.669(3) 0.2132(6) 0.7025(3) 0.103(6) Uani 0.470(15) 1 d P . .
C67 C 0.512(5) 0.5304(17) 0.8007(12) 0.387(19) Uani 1 1 d . . .
C68 C 0.348(7) 0.4104(12) 0.7521(7) 0.39(2) Uani 1 1 d . . .
O1A O 0.1920(12) 0.8471(3) 0.76227(15) 0.105(3) Uani 0.980(15) 1 d P . .
O2A O -0.0906(10) 0.7989(3) 0.79173(18) 0.058(2) Uani 0.693(14) 1 d P . .
H2AA H -0.1401 0.7981 0.7627 0.086 Uiso 0.55(11) 1 calc PR . .
O3A O 0.024(3) 0.7239(6) 0.7795(4) 0.071(6) Uani 0.326(14) 1 d P . .
H3AA H 0.0429 0.7132 0.7497 0.106 Uiso 0.19(13) 1 calc PR . .
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'
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
C1 O1 H1AA 109.5 . . ?
C30 N2 C31 117.0(4) . . ?
C23 N1 C19 117.2(4) . . ?
O2 C1 O1 123.5(4) . . ?
O2 C1 C2 124.5(4) . . ?
O1 C1 C2 112.0(3) . . ?
C8 O5 H5AA 109.5 . . ?
C21 C24 C25 113.5(3) . . ?
C21 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C21 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C8 C7 C9 111.4(3) . . ?
C8 C7 C6 111.4(4) . . ?
C9 C7 C6 111.5(3) . . ?
C8 C7 H7 105(3) . . ?
C9 C7 H7 106(3) . . ?
C6 C7 H7 111(3) . . ?
C20 C21 C22 116.3(4) . . ?
C20 C21 C24 123.6(4) . . ?
C22 C21 C24 120.1(4) . . ?
C28 C27 C26 114.3(3) . . ?
C28 C27 H27A 108.7 . . ?
C26 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C26 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C7 C9 C2 110.1(3) . . ?
C7 C9 H9A 109.6 . . ?
C2 C9 H9A 109.6 . . ?
C7 C9 H9B 109.6 . . ?
C2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
O6 C8 O5 123.3(4) . . ?
O6 C8 C7 124.3(4) . . ?
O5 C8 C7 112.4(4) . . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C3 C2 C1 111.2(3) . . ?
C3 C2 C9 111.7(4) . . ?
C1 C2 C9 111.4(3) . . ?
C3 C2 H2 107(3) . . ?
C1 C2 H2 109(3) . . ?
C9 C2 H2 107(3) . . ?
C31 C32 C28 120.0(4) . . ?
C31 C32 H32 120.0 . . ?
C28 C32 H32 120.0 . . ?
N1 C19 C20 122.8(4) . . ?
N1 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
N2 C30 C29 122.7(4) . . ?
N2 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
C29 C28 C32 116.3(4) . . ?
C29 C28 C27 123.0(4) . . ?
C32 C28 C27 120.7(4) . . ?
N2 C31 C32 123.4(4) . . ?
N2 C31 H31 118.3 . . ?
C32 C31 H31 118.3 . . ?
C26 C25 C24 112.2(3) . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
N1 C23 C22 123.6(4) . . ?
N1 C23 H23 118.2 . . ?
C22 C23 H23 118.2 . . ?
C27 C26 C25 111.8(3) . . ?
C27 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
C27 C26 H26B 109.3 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C7 C6 C4 110.3(4) . . ?
C7 C6 H6A 109.6 . . ?
C4 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C4 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C2 C3 C4 111.9(4) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C6 C4 C3 111.4(4) . . ?
C6 C4 C5 110.6(5) . . ?
C3 C4 C5 110.7(4) . . ?
C6 C4 H4 105(3) . . ?
C3 C4 H4 112(3) . . ?
C5 C4 H4 107(3) . . ?
O1A C5 O2A 116.9(7) . . ?
O1A C5 C4 125.4(8) . . ?
O2A C5 C4 114.9(6) . . ?
O1A C5 O3A 113.6(7) . . ?
O2A C5 O3A 60.5(7) . . ?
C4 C5 O3A 105.7(7) . . ?
C17 O11 H11A 109.5 . . ?
C13 C15 C16 110.0(3) . . ?
C13 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C13 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C18 112.1(4) . . ?
C17 C16 C15 110.9(3) . . ?
C18 C16 C15 110.1(4) . . ?
C17 C16 H16 110(3) . . ?
C18 C16 H16 110(3) . . ?
C15 C16 H16 104(3) . . ?
C10 O7 H7AA 109.5 . . ?
O12 C17 O11 123.6(5) . . ?
O12 C17 C16 123.9(5) . . ?
O11 C17 C16 112.5(3) . . ?
O10 C14 O9 122.9(5) . . ?
O10 C14 C13 125.3(4) . . ?
O9 C14 C13 111.8(4) . . ?
C14 C13 C12 109.7(4) . . ?
C14 C13 C15 112.5(3) . . ?
C12 C13 C15 111.6(4) . . ?
C14 C13 H13 106(3) . . ?
C12 C13 H13 109(3) . . ?
C15 C13 H13 108(3) . . ?
C14 O9 H9AA 109.5 . . ?
C16 C18 C11 112.4(4) . . ?
C16 C18 H18A 109.1 . . ?
C11 C18 H18A 109.1 . . ?
C16 C18 H18B 109.1 . . ?
C11 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C13 C12 C11 110.8(4) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C11 C10 107.6(7) . . ?
C12 C11 C18 111.5(4) . . ?
C10 C11 C18 112.2(6) . . ?
C12 C11 H11 114(4) . . ?
C10 C11 H11 110(4) . . ?
C18 C11 H11 102(4) . . ?
O7 C10 O8 120.1(7) . . ?
O7 C10 O15 88.7(8) . . ?
O8 C10 O15 89.9(7) . . ?
O7 C10 C11 117.5(8) . . ?
O8 C10 C11 119.6(7) . . ?
O15 C10 C11 108.0(8) . . ?
C37 N3 C33 118.7(5) . . ?
C43 N4 C42 116.7(4) . . ?
N4 C43 C44 124.2(5) . . ?
N4 C43 H43 117.9 . . ?
C44 C43 H43 117.9 . . ?
C36 C35 C34 117.3(5) . . ?
C36 C35 C38 122.6(5) . . ?
C34 C35 C38 120.1(5) . . ?
C35 C34 C33 117.3(5) . . ?
C35 C34 H34 121.4 . . ?
C33 C34 H34 121.4 . . ?
C44 C40 C41 116.7(4) . . ?
C44 C40 C39 120.4(5) . . ?
C41 C40 C39 122.9(5) . . ?
C37 C36 C35 121.1(5) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
N3 C37 C36 123.2(5) . . ?
N3 C37 H37 118.4 . . ?
C36 C37 H37 118.4 . . ?
C43 C44 C40 120.3(5) . . ?
C43 C44 H44 119.8 . . ?
C40 C44 H44 119.8 . . ?
N4 C42 C41 122.7(5) . . ?
N4 C42 H42 118.6 . . ?
C41 C42 H42 118.6 . . ?
C42 C41 C40 119.3(5) . . ?
C42 C41 H41 120.3 . . ?
C40 C41 H41 120.3 . . ?
C39 C38 C35 115.0(5) . . ?
C39 C38 H38A 108.5 . . ?
C35 C38 H38A 108.5 . . ?
C39 C38 H38B 108.5 . . ?
C35 C38 H38B 108.5 . . ?
H38A C38 H38B 107.5 . . ?
N3 C33 C34 122.3(4) . . ?
N3 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C38 C39 C40 117.2(5) . . ?
C38 C39 H39A 108.0 . . ?
C40 C39 H39A 108.0 . . ?
C38 C39 H39B 108.0 . . ?
C40 C39 H39B 108.0 . . ?
H39A C39 H39B 107.2 . . ?
C52 C51 C55 116.6(5) . . ?
C52 C51 C50 121.6(4) . . ?
C55 C51 C50 121.8(4) . . ?
C54 N6A C53 116.0(6) . . ?
C45 N5 C56 117.5(6) . . ?
C49 C50 C51 115.2(4) . . ?
C49 C50 H50A 108.5 . . ?
C51 C50 H50A 108.5 . . ?
C49 C50 H50B 108.5 . . ?
C51 C50 H50B 108.5 . . ?
H50A C50 H50B 107.5 . . ?
C51 C52 C53 118.2(6) . . ?
C51 C52 H52 120.9 . . ?
C53 C52 H52 120.9 . . ?
C54 C55 C51 119.3(7) . . ?
C54 C55 H55 120.4 . . ?
C51 C55 H55 120.4 . . ?
C45 C46 C47 121.2(6) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 H46 119.4 . . ?
C46 C47 C48 115.9(6) . . ?
C46 C47 C49 122.3(5) . . ?
C48 C47 C49 121.8(5) . . ?
C56 C48 C47 120.3(5) . . ?
C56 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
N6A C53 C52 123.4(7) . . ?
N6A C53 H53 118.3 . . ?
C52 C53 H53 118.3 . . ?
N5 C45 C46 122.0(5) . . ?
N5 C45 H45 119.0 . . ?
C46 C45 H45 119.0 . . ?
C50 C49 C47 113.2(4) . . ?
C50 C49 H49A 108.9 . . ?
C47 C49 H49A 108.9 . . ?
C50 C49 H49B 108.9 . . ?
C47 C49 H49B 108.9 . . ?
H49A C49 H49B 107.7 . . ?
N6A C54 C55 126.5(9) . . ?
N6A C54 H54 116.8 . . ?
C55 C54 H54 116.8 . . ?
N5 C56 C48 123.2(6) . . ?
N5 C56 H56 118.4 . . ?
C48 C56 H56 118.4 . . ?
C57 O13 H13A 109.5 . . ?
C63 C58 C59 110.8(11) . . ?
C63 C58 C68 82.8(13) . . ?
C59 C58 C68 166.2(13) . . ?
O16 C62 C59 139.9(12) . . ?
O16 C62 C65 57.4(9) . . ?
C59 C62 C65 121.5(12) . . ?
C67 C57 O13 153(2) . . ?
C67 C57 C68 128(2) . . ?
O13 C57 C68 61.3(9) . . ?
C67 C57 C63 66.8(19) . . ?
O13 C57 C63 112.9(8) . . ?
C68 C57 C63 62.1(11) . . ?
C63 C64 C65 109.4(13) . . ?
C63 C64 C67 68.3(12) . . ?
C65 C64 C67 177.6(13) . . ?
C64 C63 C58 141.8(17) . . ?
C64 C63 C67 71.2(13) . . ?
C58 C63 C67 146.7(17) . . ?
C64 C63 C57 107.6(12) . . ?
C58 C63 C57 110.5(9) . . ?
C67 C63 C57 36.4(12) . . ?
C64 C63 C68 165(2) . . ?
C58 C63 C68 52.8(12) . . ?
C67 C63 C68 93.9(19) . . ?
C57 C63 C68 57.7(13) . . ?
C62 C59 C58 119.7(11) . . ?
C62 C65 C64 116.7(11) . . ?
C57 C67 C63 76.8(16) . . ?
C57 C67 C64 117(2) . . ?
C63 C67 C64 40.5(9) . . ?
C58 C68 C57 104.5(14) . . ?
C58 C68 C63 44.4(9) . . ?
C57 C68 C63 60.2(9) . . ?
C5 O2A H2AA 109.5 . . ?
C5 O3A H3AA 109.5 . . ?
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
O1 C1 1.321(5) . ?
O1 H1AA 0.8400 . ?
O2 C1 1.206(5) . ?
O6 C8 1.206(5) . ?
N2 C30 1.343(5) . ?
N2 C31 1.346(6) . ?
N1 C23 1.330(6) . ?
N1 C19 1.330(5) . ?
C1 C2 1.513(5) . ?
O5 C8 1.319(5) . ?
O5 H5AA 0.8400 . ?
C24 C21 1.503(6) . ?
C24 C25 1.523(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C7 C8 1.503(6) . ?
C7 C9 1.520(5) . ?
C7 C6 1.525(6) . ?
C7 H7 0.92(5) . ?
C21 C20 1.381(6) . ?
C21 C22 1.393(6) . ?
C27 C28 1.500(6) . ?
C27 C26 1.520(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C29 C30 1.380(6) . ?
C29 C28 1.386(6) . ?
C29 H29 0.9500 . ?
C9 C2 1.533(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C20 C19 1.381(6) . ?
C20 H20 0.9500 . ?
C2 C3 1.512(6) . ?
C2 H2 0.96(5) . ?
C32 C31 1.370(6) . ?
C32 C28 1.403(6) . ?
C32 H32 0.9500 . ?
C19 H19 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C25 C26 1.521(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 C22 1.374(6) . ?
C23 H23 0.9500 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C22 H22 0.9500 . ?
C6 C4 1.526(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 C4 1.528(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.530(8) . ?
C4 H4 1.02(6) . ?
C5 O1A 1.134(8) . ?
C5 O2A 1.218(8) . ?
C5 O3A 1.795(14) . ?
O11 C17 1.319(5) . ?
O11 H11A 0.8400 . ?
O10 C14 1.203(6) . ?
C15 C13 1.519(5) . ?
C15 C16 1.538(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.499(6) . ?
C16 C18 1.530(6) . ?
C16 H16 1.01(5) . ?
O12 C17 1.210(5) . ?
O7 C10 1.185(8) . ?
O7 H7AA 0.8400 . ?
C14 O9 1.316(6) . ?
C14 C13 1.501(7) . ?
C13 C12 1.511(7) . ?
C13 H13 0.88(5) . ?
O9 H9AA 0.8400 . ?
C18 C11 1.531(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C12 C11 1.514(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.525(8) . ?
C11 H11 0.91(7) . ?
O8 C10 1.350(11) . ?
C10 O15 1.523(15) . ?
N3 C37 1.297(6) . ?
N3 C33 1.315(7) . ?
N4 C43 1.332(6) . ?
N4 C42 1.340(6) . ?
C43 C44 1.342(7) . ?
C43 H43 0.9500 . ?
C35 C36 1.376(7) . ?
C35 C34 1.376(7) . ?
C35 C38 1.512(7) . ?
C34 C33 1.434(8) . ?
C34 H34 0.9500 . ?
C40 C44 1.373(7) . ?
C40 C41 1.398(7) . ?
C40 C39 1.504(7) . ?
C36 C37 1.347(7) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C44 H44 0.9500 . ?
C42 C41 1.374(7) . ?
C42 H42 0.9500 . ?
C41 H41 0.9500 . ?
C38 C39 1.465(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C33 H33 0.9500 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C51 C52 1.378(7) . ?
C51 C55 1.378(7) . ?
C51 C50 1.504(6) . ?
N6A C54 1.282(13) . ?
N6A C53 1.317(11) . ?
N5 C45 1.333(8) . ?
N5 C56 1.334(7) . ?
C50 C49 1.497(7) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C52 C53 1.402(9) . ?
C52 H52 0.9500 . ?
C55 C54 1.339(9) . ?
C55 H55 0.9500 . ?
C46 C45 1.366(9) . ?
C46 C47 1.377(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.386(8) . ?
C47 C49 1.513(8) . ?
C48 C56 1.354(8) . ?
C48 H48 0.9500 . ?
C53 H53 0.9500 . ?
C45 H45 0.9500 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C54 H54 0.9500 . ?
C56 H56 0.9500 . ?
O13 C57 1.321(10) . ?
O13 H13A 0.8400 . ?
C58 C63 1.296(13) . ?
C58 C59 1.434(13) . ?
C58 C68 1.48(4) . ?
C62 O16 1.313(17) . ?
C62 C59 1.342(13) . ?
C62 C65 1.411(19) . ?
C57 C67 1.10(3) . ?
C57 C68 1.76(3) . ?
C57 C63 1.807(18) . ?
C64 C63 1.191(12) . ?
C64 C65 1.526(19) . ?
C64 C67 1.74(3) . ?
C63 C67 1.71(3) . ?
C63 C68 1.84(3) . ?
O2A H2AA 0.8400 . ?
O3A H3AA 0.8400 . ?
