#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/43/7214321.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_7214321
loop_
_publ_author_name
'Beyeh, N. Kodiah'
'Valkonen, Arto'
'Rissanen, Kari'
_publ_section_title
;
 Deprotonation of resorcinarenes by mono- and diamine bases: complexation
 and intermolecular interactions in the solid state
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              3758
_journal_paper_doi               10.1039/c3ce42291g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C40 H47 O8, C3 H8 N, C H4 O, 2(C3 H7 N)'
_chemical_formula_sum            'C50 H73 N3 O9'
_chemical_formula_weight         860.11
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                107.092(2)
_cell_angle_beta                 94.407(2)
_cell_angle_gamma                110.946(2)
_cell_formula_units_Z            2
_cell_length_a                   11.7076(5)
_cell_length_b                   14.7176(6)
_cell_length_c                   15.4943(6)
_cell_measurement_temperature    173(2)
_cell_volume                     2333.23(17)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, et al., 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_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  0.0804
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29369
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.291
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0965 before and 0.0848 after correction.
The Ratio of minimum to maximum transmission is 0.7841.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         8194
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0707
_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)+(0.0456P)²+3.2979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5833
_reflns_number_total             8194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3ce42291g.txt
_cod_data_source_block           III
_cod_database_code               7214321
#BEGIN Tags that were not found in dictionaries:
_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   0.977
_shelx_estimated_absorpt_t_max   0.990
#END Tags that were not found in dictionaries
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
O1 O 1.0447(2) 0.82562(18) 0.24180(16) 0.0299(5) Uani 1 1 d D .
H1O H 1.1205(19) 0.866(3) 0.260(3) 0.045 Uiso 1 1 d D U
O2 O 1.0498(2) 0.48523(17) 0.14542(15) 0.0281(5) Uani 1 1 d D .
H2O H 1.124(2) 0.508(3) 0.137(3) 0.042 Uiso 1 1 d D U
O3 O 0.8854(2) 0.28552(18) 0.09525(16) 0.0304(5) Uani 1 1 d D .
H3O H 0.937(3) 0.3476(17) 0.112(3) 0.046 Uiso 1 1 d D U
O4 O 0.4490(2) 0.13138(18) 0.05942(16) 0.0338(6) Uani 1 1 d D .
H4O H 0.388(3) 0.147(3) 0.073(3) 0.051 Uiso 1 1 d D U
O5 O 0.2564(2) 0.19032(17) 0.08288(15) 0.0269(5) Uani 1 1 d D .
H5O H 0.181(2) 0.159(3) 0.087(3) 0.040 Uiso 1 1 d D U
O6 O 0.27835(19) 0.53206(16) 0.12505(14) 0.0256(5) Uani 1 1 d . .
O7 O 0.4303(2) 0.73651(18) 0.19219(16) 0.0311(5) Uani 1 1 d D .
H7O H 0.378(3) 0.6743(17) 0.179(3) 0.047 Uiso 1 1 d D U
O8 O 0.8693(2) 0.90433(18) 0.26018(17) 0.0321(6) Uani 1 1 d D .
H8O H 0.929(3) 0.887(3) 0.259(3) 0.048 Uiso 1 1 d D U
C1 C 0.9435(3) 0.7064(2) 0.3160(2) 0.0232(7) Uani 1 1 d . .
C2 C 1.0149(3) 0.7295(2) 0.2512(2) 0.0242(7) Uani 1 1 d . .
C3 C 1.0514(3) 0.6575(3) 0.1925(2) 0.0260(7) Uani 1 1 d . .
C4 C 1.0203(3) 0.5612(3) 0.2039(2) 0.0245(7) Uani 1 1 d . .
C5 C 0.9521(3) 0.5349(2) 0.2696(2) 0.0232(7) Uani 1 1 d . .
C6 C 0.9137(3) 0.6085(2) 0.3233(2) 0.0234(7) Uani 1 1 d . .
H6 H 0.8650 0.5913 0.3669 0.028 Uiso 1 1 calc R U
C7 C 0.9210(3) 0.4294(2) 0.2807(2) 0.0242(7) Uani 1 1 d . .
H7 H 0.9843 0.4039 0.2555 0.029 Uiso 1 1 calc R U
C8 C 0.9351(3) 0.4359(3) 0.3821(2) 0.0278(7) Uani 1 1 d . .
H8A H 1.0175 0.4906 0.4171 0.033 Uiso 1 1 calc R U
H8B H 0.8699 0.4561 0.4088 0.033 Uiso 1 1 calc R U
C9 C 0.9241(4) 0.3340(3) 0.3931(3) 0.0415(9) Uani 1 1 d . .
H9A H 0.8412 0.2803 0.3609 0.062 Uiso 1 1 calc R U
H9B H 0.9355 0.3425 0.4587 0.062 Uiso 1 1 calc R U
H9C H 0.9883 0.3135 0.3668 0.062 Uiso 1 1 calc R U
C10 C 1.1198(3) 0.6826(3) 0.1186(2) 0.0318(8) Uani 1 1 d . .
H10A H 1.2099 0.7165 0.1440 0.048 Uiso 1 1 calc R U
H10B H 1.0927 0.7292 0.0968 0.048 Uiso 1 1 calc R U
H10C H 1.1014 0.6185 0.0671 0.048 Uiso 1 1 calc R U
C11 C 0.7937(3) 0.3494(2) 0.2225(2) 0.0239(7) Uani 1 1 d . .
C12 C 0.7824(3) 0.2824(2) 0.1343(2) 0.0243(7) Uani 1 1 d . .
C13 C 0.6674(3) 0.2084(3) 0.0805(2) 0.0267(7) Uani 1 1 d . .
C14 C 0.5595(3) 0.2037(2) 0.1161(2) 0.0262(7) Uani 1 1 d . .
C15 C 0.5659(3) 0.2691(2) 0.2044(2) 0.0234(7) Uani 1 1 d . .
C16 C 0.6840(3) 0.3413(2) 0.2549(2) 0.0231(7) Uani 1 1 d . .
H16 H 0.6899 0.3872 0.3144 0.028 Uiso 1 1 calc R U
C17 C 0.4478(3) 0.2614(2) 0.2420(2) 0.0235(7) Uani 1 1 d . .
H17 H 0.3852 0.1887 0.2098 0.028 Uiso 1 1 calc R U
C18 C 0.4652(3) 0.2786(3) 0.3453(2) 0.0282(7) Uani 1 1 d . .
H18A H 0.5104 0.2375 0.3595 0.034 Uiso 1 1 calc R U
H18B H 0.5166 0.3527 0.3806 0.034 Uiso 1 1 calc R U
C19 C 0.3395(3) 0.2466(3) 0.3752(2) 0.0418(9) Uani 1 1 d . .
H19A H 0.2874 0.1739 0.3388 0.063 Uiso 1 1 calc R U
H19B H 0.2972 0.2904 0.3652 0.063 Uiso 1 1 calc R U
H19C H 0.3532 0.2549 0.4408 0.063 Uiso 1 1 calc R U
C20 C 0.6564(3) 0.1363(3) -0.0150(2) 0.0336(8) Uani 1 1 d . .
H20A H 0.6128 0.0643 -0.0185 0.050 Uiso 1 1 calc R U
H20B H 0.7400 0.1471 -0.0278 0.050 Uiso 1 1 calc R U
H20C H 0.6092 0.1506 -0.0606 0.050 Uiso 1 1 calc R U
C21 C 0.3932(3) 0.3315(2) 0.2156(2) 0.0227(7) Uani 1 1 d . .
C22 C 0.3002(3) 0.2932(2) 0.1366(2) 0.0242(7) Uani 1 1 d . .
C23 C 0.2563(3) 0.3590(2) 0.1074(2) 0.0235(7) Uani 1 1 d . .
C24 C 0.3068(3) 0.4656(2) 0.1591(2) 0.0229(7) Uani 1 1 d . .
C25 C 0.3901(3) 0.5036(2) 0.2440(2) 0.0227(7) Uani 1 1 d . .
C26 C 0.4344(3) 0.4362(2) 0.2684(2) 0.0238(7) Uani 1 1 d . .
H26 H 0.4955 0.4631 0.3235 0.029 Uiso 1 1 calc R U
C27 C 0.4259(3) 0.6143(2) 0.3087(2) 0.0240(7) Uani 1 1 d . .
H27 H 0.3581 0.6353 0.2903 0.029 Uiso 1 1 calc R U
C28 C 0.4246(3) 0.6202(3) 0.4092(2) 0.0285(7) Uani 1 1 d . .
H28A H 0.4812 0.5899 0.4280 0.034 Uiso 1 1 calc R U
H28B H 0.4564 0.6937 0.4496 0.034 Uiso 1 1 calc R U
C29 C 0.2940(3) 0.5626(3) 0.4223(3) 0.0455(10) Uani 1 1 d . .
H29A H 0.2634 0.4892 0.3842 0.068 Uiso 1 1 calc R U
H29B H 0.2377 0.5924 0.4039 0.068 Uiso 1 1 calc R U
H29C H 0.2969 0.5691 0.4873 0.068 Uiso 1 1 calc R U
C30 C 0.1573(3) 0.3138(2) 0.0200(2) 0.0265(7) Uani 1 1 d . .
H30A H 0.0760 0.2760 0.0321 0.040 Uiso 1 1 calc R U
H30B H 0.1787 0.2661 -0.0284 0.040 Uiso 1 1 calc R U
H30C H 0.1534 0.3699 -0.0003 0.040 Uiso 1 1 calc R U
C31 C 0.5454(3) 0.6908(2) 0.2968(2) 0.0235(7) Uani 1 1 d . .
C32 C 0.5424(3) 0.7493(2) 0.2404(2) 0.0250(7) Uani 1 1 d . .
C33 C 0.6506(3) 0.8221(2) 0.2300(2) 0.0260(7) Uani 1 1 d . .
C34 C 0.7664(3) 0.8330(2) 0.2746(2) 0.0252(7) Uani 1 1 d . .
C35 C 0.7753(3) 0.7756(2) 0.3305(2) 0.0243(7) Uani 1 1 d . .
C36 C 0.6638(3) 0.7053(2) 0.3397(2) 0.0235(7) Uani 1 1 d . .
H36 H 0.6682 0.6652 0.3770 0.028 Uiso 1 1 calc R U
C37 C 0.9021(3) 0.7860(2) 0.3769(2) 0.0244(7) Uani 1 1 d . .
H37 H 0.9640 0.8555 0.3809 0.029 Uiso 1 1 calc R U
C38 C 0.9071(3) 0.7863(3) 0.4764(2) 0.0272(7) Uani 1 1 d . .
H38A H 0.8345 0.7263 0.4777 0.033 Uiso 1 1 calc R U
H38B H 0.9838 0.7781 0.4973 0.033 Uiso 1 1 calc R U
C39 C 0.9064(4) 0.8853(3) 0.5429(2) 0.0389(9) Uani 1 1 d . .
H39A H 0.8304 0.8936 0.5229 0.058 Uiso 1 1 calc R U
H39B H 0.9798 0.9448 0.5437 0.058 Uiso 1 1 calc R U
H39C H 0.9083 0.8812 0.6050 0.058 Uiso 1 1 calc R U
C40 C 0.6469(3) 0.8862(3) 0.1707(3) 0.0361(8) Uani 1 1 d . .
H40A H 0.6930 0.8725 0.1216 0.054 Uiso 1 1 calc R U
H40B H 0.6854 0.9599 0.2086 0.054 Uiso 1 1 calc R U
H40C H 0.5599 0.8679 0.1432 0.054 Uiso 1 1 calc R U
N1 N 0.3863(2) 0.5155(2) -0.02371(18) 0.0264(6) Uani 1 1 d D .
H1N H 0.353(3) 0.517(3) 0.0292(16) 0.028(9) Uiso 1 1 d D .
C41 C 0.5108(3) 0.6037(3) 0.0120(2) 0.0291(8) Uani 1 1 d . .
H41A H 0.5005 0.6672 0.0476 0.035 Uiso 1 1 calc R U
H41B H 0.5492 0.6163 -0.0404 0.035 Uiso 1 1 calc R U
C42 C 0.5955(3) 0.5805(3) 0.0732(2) 0.0303(8) Uani 1 1 d . .
H42A H 0.6777 0.6399 0.0959 0.036 Uiso 1 1 calc R U
H42B H 0.5591 0.5722 0.1274 0.036 Uiso 1 1 calc R U
C43 C 0.3037(3) 0.5367(3) -0.0868(3) 0.0404(9) Uani 1 1 d . .
H43A H 0.3422 0.5462 -0.1393 0.061 Uiso 1 1 calc R U
H43B H 0.2927 0.5997 -0.0533 0.061 Uiso 1 1 calc R U
H43C H 0.2222 0.4780 -0.1093 0.061 Uiso 1 1 calc R U
N2 N 0.0314(2) 0.0800(2) 0.08864(19) 0.0313(7) Uani 1 1 d . .
C44 C 0.0462(3) -0.0175(3) 0.0785(3) 0.0363(9) Uani 1 1 d . .
H44A H -0.0309 -0.0686 0.0863 0.044 Uiso 1 1 calc R U
H44B H 0.1162 -0.0048 0.1268 0.044 Uiso 1 1 calc R U
C45 C -0.0721(3) 0.0604(3) 0.0154(2) 0.0349(8) Uani 1 1 d . .
H45A H -0.0822 0.1258 0.0216 0.042 Uiso 1 1 calc R U
H45B H -0.1510 0.0104 0.0223 0.042 Uiso 1 1 calc R U
C46 C 0.0086(4) 0.1254(3) 0.1812(3) 0.0447(10) Uani 1 1 d . .
H46A H -0.0659 0.0752 0.1914 0.067 Uiso 1 1 calc R U
H46B H -0.0044 0.1885 0.1849 0.067 Uiso 1 1 calc R U
H46C H 0.0810 0.1424 0.2284 0.067 Uiso 1 1 calc R U
N3 N 1.3655(3) 0.9503(3) 0.4747(2) 0.0447(8) Uani 1 1 d . .
C47 C 1.4302(4) 1.0483(3) 0.5521(3) 0.0471(10) Uani 1 1 d . .
H47A H 1.4405 1.0337 0.6099 0.057 Uiso 1 1 calc R U
H47B H 1.3792 1.0901 0.5584 0.057 Uiso 1 1 calc R U
C48 C 1.5568(4) 1.1092(3) 0.5371(3) 0.0465(10) Uani 1 1 d . .
H48A H 1.5461 1.1281 0.4817 0.056 Uiso 1 1 calc R U
H48B H 1.5992 1.1742 0.5907 0.056 Uiso 1 1 calc R U
C49 C 1.2445(4) 0.8923(4) 0.4915(3) 0.0673(14) Uani 1 1 d . .
H49A H 1.2033 0.8257 0.4409 0.101 Uiso 1 1 calc R U
H49B H 1.1924 0.9321 0.4951 0.101 Uiso 1 1 calc R U
H49C H 1.2566 0.8801 0.5497 0.101 Uiso 1 1 calc R U
O9 O 1.2759(2) 0.9589(2) 0.30791(19) 0.0476(7) Uani 1 1 d D .
H9O H 1.310(4) 0.947(4) 0.355(2) 0.071 Uiso 1 1 d D U
C50 C 1.3655(4) 0.9751(3) 0.2518(3) 0.0467(10) Uani 1 1 d . .
H50A H 1.4384 1.0394 0.2854 0.070 Uiso 1 1 calc R U
H50B H 1.3290 0.9803 0.1953 0.070 Uiso 1 1 calc R U
H50C H 1.3913 0.9168 0.2358 0.070 Uiso 1 1 calc R U
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
C2 O1 H1O 115(3) . .
C4 O2 H2O 113(3) . .
C12 O3 H3O 109(3) . .
C14 O4 H4O 112(3) . .
C22 O5 H5O 110(3) . .
C32 O7 H7O 109(3) . .
C34 O8 H8O 112(3) . .
C2 C1 C6 117.3(3) . .
C2 C1 C37 120.8(3) . .
C6 C1 C37 121.9(3) . .
O1 C2 C1 118.5(3) . .
O1 C2 C3 119.0(3) . .
C1 C2 C3 122.4(3) . .
C2 C3 C4 117.7(3) . .
C2 C3 C10 120.7(3) . .
C4 C3 C10 121.6(3) . .
O2 C4 C5 117.3(3) . .
O2 C4 C3 120.3(3) . .
C5 C4 C3 122.3(3) . .
C6 C5 C4 117.2(3) . .
C6 C5 C7 122.0(3) . .
C4 C5 C7 120.8(3) . .
C5 C6 C1 123.0(3) . .
C5 C6 H6 118.5 . .
C1 C6 H6 118.5 . .
C11 C7 C5 112.1(2) . .
C11 C7 C8 112.4(3) . .
C5 C7 C8 113.0(3) . .
C11 C7 H7 106.2 . .
C5 C7 H7 106.2 . .
C8 C7 H7 106.2 . .
C9 C8 C7 112.5(3) . .
C9 C8 H8A 109.1 . .
C7 C8 H8A 109.1 . .
C9 C8 H8B 109.1 . .
C7 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C3 C10 H10A 109.5 . .
C3 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C3 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C16 C11 C12 117.2(3) . .
C16 C11 C7 121.4(3) . .
C12 C11 C7 121.4(3) . .
O3 C12 C13 116.0(3) . .
O3 C12 C11 121.7(3) . .
C13 C12 C11 122.3(3) . .
C12 C13 C14 118.3(3) . .
C12 C13 C20 121.8(3) . .
C14 C13 C20 119.9(3) . .
O4 C14 C15 122.6(3) . .
O4 C14 C13 115.8(3) . .
C15 C14 C13 121.6(3) . .
C16 C15 C14 117.3(3) . .
C16 C15 C17 122.1(3) . .
C14 C15 C17 120.6(3) . .
C11 C16 C15 123.3(3) . .
C11 C16 H16 118.3 . .
C15 C16 H16 118.3 . .
C15 C17 C21 110.4(2) . .
C15 C17 C18 113.4(2) . .
C21 C17 C18 113.0(3) . .
C15 C17 H17 106.5 . .
C21 C17 H17 106.5 . .
C18 C17 H17 106.5 . .
C19 C18 C17 111.3(3) . .
C19 C18 H18A 109.4 . .
C17 C18 H18A 109.4 . .
C19 C18 H18B 109.4 . .
C17 C18 H18B 109.4 . .
H18A C18 H18B 108.0 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C13 C20 H20A 109.5 . .
C13 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C13 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C26 C21 C22 117.4(3) . .
C26 C21 C17 121.7(3) . .
C22 C21 C17 120.9(3) . .
O5 C22 C21 119.3(3) . .
O5 C22 C23 119.1(3) . .
C21 C22 C23 121.4(3) . .
C24 C23 C22 119.3(3) . .
C24 C23 C30 121.4(3) . .
C22 C23 C30 119.3(3) . .
O6 C24 C25 120.2(3) . .
O6 C24 C23 119.8(3) . .
C25 C24 C23 119.9(3) . .
C26 C25 C24 118.3(3) . .
C26 C25 C27 121.5(3) . .
C24 C25 C27 120.2(3) . .
C21 C26 C25 123.1(3) . .
C21 C26 H26 118.5 . .
C25 C26 H26 118.5 . .
C31 C27 C25 113.1(2) . .
C31 C27 C28 113.5(3) . .
C25 C27 C28 111.9(3) . .
C31 C27 H27 105.9 . .
C25 C27 H27 105.9 . .
C28 C27 H27 105.9 . .
C29 C28 C27 112.0(3) . .
C29 C28 H28A 109.2 . .
C27 C28 H28A 109.2 . .
C29 C28 H28B 109.2 . .
C27 C28 H28B 109.2 . .
H28A C28 H28B 107.9 . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C23 C30 H30A 109.5 . .
C23 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C23 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C32 C31 C36 116.8(3) . .
C32 C31 C27 121.0(3) . .
C36 C31 C27 122.2(3) . .
O7 C32 C33 116.9(3) . .
O7 C32 C31 120.8(3) . .
C33 C32 C31 122.3(3) . .
C32 C33 C34 118.1(3) . .
C32 C33 C40 122.2(3) . .
C34 C33 C40 119.7(3) . .
O8 C34 C35 122.5(3) . .
O8 C34 C33 115.4(3) . .
C35 C34 C33 122.1(3) . .
C36 C35 C34 117.2(3) . .
C36 C35 C37 121.1(3) . .
C34 C35 C37 121.7(3) . .
C35 C36 C31 123.4(3) . .
C35 C36 H36 118.3 . .
C31 C36 H36 118.3 . .
C1 C37 C35 110.8(2) . .
C1 C37 C38 113.3(3) . .
C35 C37 C38 113.5(3) . .
C1 C37 H37 106.2 . .
C35 C37 H37 106.2 . .
C38 C37 H37 106.2 . .
C39 C38 C37 112.6(3) . .
C39 C38 H38A 109.1 . .
C37 C38 H38A 109.1 . .
C39 C38 H38B 109.1 . .
C37 C38 H38B 109.1 . .
H38A C38 H38B 107.8 . .
C38 C39 H39A 109.5 . .
C38 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C33 C40 H40A 109.5 . .
C33 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
C33 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C41 N1 C42 108.7(2) . 2_665
C41 N1 C43 110.6(3) . .
C42 N1 C43 110.6(3) 2_665 .
C41 N1 H1N 103(2) . .
C42 N1 H1N 118(2) 2_665 .
C43 N1 H1N 106(2) . .
N1 C41 C42 110.5(3) . .
N1 C41 H41A 109.6 . .
C42 C41 H41A 109.6 . .
N1 C41 H41B 109.6 . .
C42 C41 H41B 109.6 . .
H41A C41 H41B 108.1 . .
N1 C42 C41 112.2(3) 2_665 .
N1 C42 H42A 109.2 2_665 .
C41 C42 H42A 109.2 . .
N1 C42 H42B 109.2 2_665 .
C41 C42 H42B 109.2 . .
H42A C42 H42B 107.9 . .
N1 C43 H43A 109.5 . .
N1 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
N1 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
C44 N2 C45 109.2(3) . .
C44 N2 C46 111.4(3) . .
C45 N2 C46 110.8(3) . .
N2 C44 C45 110.1(3) . 2
N2 C44 H44A 109.6 . .
C45 C44 H44A 109.6 2 .
N2 C44 H44B 109.6 . .
C45 C44 H44B 109.6 2 .
H44A C44 H44B 108.2 . .
N2 C45 C44 110.5(3) . 2
N2 C45 H45A 109.5 . .
C44 C45 H45A 109.5 2 .
N2 C45 H45B 109.5 . .
C44 C45 H45B 109.5 2 .
H45A C45 H45B 108.1 . .
N2 C46 H46A 109.5 . .
N2 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
N2 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C49 N3 C48 111.2(3) . 2_876
C49 N3 C47 109.8(3) . .
C48 N3 C47 109.4(3) 2_876 .
N3 C47 C48 110.9(3) . .
N3 C47 H47A 109.5 . .
C48 C47 H47A 109.5 . .
N3 C47 H47B 109.5 . .
C48 C47 H47B 109.5 . .
H47A C47 H47B 108.0 . .
N3 C48 C47 111.3(3) 2_876 .
N3 C48 H48A 109.4 2_876 .
C47 C48 H48A 109.4 . .
N3 C48 H48B 109.4 2_876 .
C47 C48 H48B 109.4 . .
H48A C48 H48B 108.0 . .
N3 C49 H49A 109.5 . .
N3 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
N3 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
C50 O9 H9O 106(3) . .
O9 C50 H50A 109.5 . .
O9 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
O9 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
O1 C2 1.385(4) .
O1 H1O 0.839(19) .
O2 C4 1.385(4) .
O2 H2O 0.850(18) .
O3 C12 1.383(4) .
O3 H3O 0.844(19) .
O4 C14 1.367(4) .
O4 H4O 0.844(19) .
O5 C22 1.373(4) .
O5 H5O 0.857(18) .
O6 C24 1.363(4) .
O7 C32 1.381(4) .
O7 H7O 0.849(19) .
O8 C34 1.370(4) .
O8 H8O 0.832(19) .
C1 C2 1.396(4) .
C1 C6 1.397(4) .
C1 C37 1.524(4) .
C2 C3 1.397(4) .
C3 C4 1.400(5) .
C3 C10 1.505(4) .
C4 C5 1.399(4) .
C5 C6 1.395(4) .
C5 C7 1.528(4) .
C6 H6 0.9500 .
C7 C11 1.528(4) .
C7 C8 1.539(4) .
C7 H7 1.0000 .
C8 C9 1.520(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C16 1.393(4) .
C11 C12 1.394(4) .
C12 C13 1.392(4) .
C13 C14 1.405(4) .
C13 C20 1.511(4) .
C14 C15 1.400(4) .
C15 C16 1.396(4) .
C15 C17 1.522(4) .
C16 H16 0.9500 .
C17 C21 1.523(4) .
C17 C18 1.532(4) .
C17 H17 1.0000 .
C18 C19 1.530(5) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
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 C26 1.394(4) .
C21 C22 1.397(4) .
C22 C23 1.409(4) .
C23 C24 1.406(4) .
C23 C30 1.516(4) .
C24 C25 1.404(4) .
C25 C26 1.397(4) .
C25 C27 1.525(4) .
C26 H26 0.9500 .
C27 C31 1.515(4) .
C27 C28 1.536(4) .
C27 H27 1.0000 .
C28 C29 1.523(5) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 C32 1.401(4) .
C31 C36 1.405(4) .
C32 C33 1.394(4) .
C33 C34 1.406(4) .
C33 C40 1.505(5) .
C34 C35 1.398(4) .
C35 C36 1.394(4) .
C35 C37 1.534(4) .
C36 H36 0.9500 .
C37 C38 1.538(4) .
C37 H37 1.0000 .
C38 C39 1.520(5) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
N1 C41 1.489(4) .
N1 C42 1.494(4) 2_665
N1 C43 1.496(4) .
N1 H1N 0.934(18) .
C41 C42 1.513(4) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
C42 N1 1.494(4) 2_665
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
N2 C44 1.471(4) .
N2 C45 1.478(4) .
N2 C46 1.482(5) .
C44 C45 1.507(5) 2
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 C44 1.507(5) 2
C45 H45A 0.9900 .
C45 H45B 0.9900 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
N3 C49 1.458(5) .
N3 C48 1.460(5) 2_876
N3 C47 1.468(5) .
C47 C48 1.509(6) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 N3 1.460(5) 2_876
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
O9 C50 1.413(5) .
O9 H9O 0.892(19) .
C50 H50A 0.9800 .
C50 H50B 0.9800 .
C50 H50C 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
O1 H1O O9 0.839(19) 1.78(2) 2.611(3) 173(4) .
O2 H2O O6 0.850(18) 1.75(2) 2.584(3) 167(4) 1_655
O3 H3O O2 0.844(19) 1.864(19) 2.707(3) 178(4) .
O4 H4O O5 0.844(19) 1.87(2) 2.703(3) 169(4) .
O5 H5O N2 0.857(18) 1.73(2) 2.578(3) 172(4) .
O7 H7O O6 0.849(19) 1.88(2) 2.711(3) 167(4) .
O8 H8O O1 0.832(19) 1.87(2) 2.691(3) 170(4) .
N1 H1N O6 0.934(18) 1.776(19) 2.703(3) 172(3) .
O9 H9O N3 0.892(19) 1.90(2) 2.768(4) 163(4) .
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
C6 C1 C2 O1 179.3(3) . .
C37 C1 C2 O1 -1.6(4) . .
C6 C1 C2 C3 2.8(4) . .
C37 C1 C2 C3 -178.1(3) . .
O1 C2 C3 C4 179.8(3) . .
C1 C2 C3 C4 -3.7(4) . .
O1 C2 C3 C10 -1.3(4) . .
C1 C2 C3 C10 175.2(3) . .
C2 C3 C4 O2 177.5(3) . .
C10 C3 C4 O2 -1.4(4) . .
C2 C3 C4 C5 1.7(4) . .
C10 C3 C4 C5 -177.2(3) . .
O2 C4 C5 C6 -174.9(3) . .
C3 C4 C5 C6 1.1(4) . .
O2 C4 C5 C7 4.6(4) . .
C3 C4 C5 C7 -179.4(3) . .
C4 C5 C6 C1 -2.0(4) . .
C7 C5 C6 C1 178.4(3) . .
C2 C1 C6 C5 0.2(4) . .
C37 C1 C6 C5 -178.9(3) . .
C6 C5 C7 C11 86.7(3) . .
C4 C5 C7 C11 -92.8(3) . .
C6 C5 C7 C8 -41.5(4) . .
C4 C5 C7 C8 139.0(3) . .
C11 C7 C8 C9 61.0(4) . .
C5 C7 C8 C9 -170.9(3) . .
C5 C7 C11 C16 -85.3(4) . .
C8 C7 C11 C16 43.3(4) . .
C5 C7 C11 C12 93.9(3) . .
C8 C7 C11 C12 -137.5(3) . .
C16 C11 C12 O3 178.9(3) . .
C7 C11 C12 O3 -0.4(4) . .
C16 C11 C12 C13 -1.3(5) . .
C7 C11 C12 C13 179.5(3) . .
O3 C12 C13 C14 -178.6(3) . .
C11 C12 C13 C14 1.6(5) . .
O3 C12 C13 C20 -0.2(4) . .
C11 C12 C13 C20 180.0(3) . .
C12 C13 C14 O4 178.4(3) . .
C20 C13 C14 O4 0.0(4) . .
C12 C13 C14 C15 -1.7(5) . .
C20 C13 C14 C15 179.9(3) . .
O4 C14 C15 C16 -178.6(3) . .
C13 C14 C15 C16 1.5(5) . .
O4 C14 C15 C17 0.7(5) . .
C13 C14 C15 C17 -179.2(3) . .
C12 C11 C16 C15 1.1(5) . .
C7 C11 C16 C15 -179.7(3) . .
C14 C15 C16 C11 -1.2(5) . .
C17 C15 C16 C11 179.5(3) . .
C16 C15 C17 C21 90.3(3) . .
C14 C15 C17 C21 -89.0(3) . .
C16 C15 C17 C18 -37.8(4) . .
C14 C15 C17 C18 142.9(3) . .
C15 C17 C18 C19 -167.3(3) . .
C21 C17 C18 C19 66.0(4) . .
C15 C17 C21 C26 -85.1(3) . .
C18 C17 C21 C26 43.1(4) . .
C15 C17 C21 C22 94.2(3) . .
C18 C17 C21 C22 -137.5(3) . .
C26 C21 C22 O5 -179.7(3) . .
C17 C21 C22 O5 0.9(4) . .
C26 C21 C22 C23 4.7(4) . .
C17 C21 C22 C23 -174.7(3) . .
O5 C22 C23 C24 -175.9(3) . .
C21 C22 C23 C24 -0.2(4) . .
O5 C22 C23 C30 2.9(4) . .
C21 C22 C23 C30 178.6(3) . .
C22 C23 C24 O6 170.8(3) . .
C30 C23 C24 O6 -8.0(4) . .
C22 C23 C24 C25 -6.8(4) . .
C30 C23 C24 C25 174.4(3) . .
O6 C24 C25 C26 -168.5(3) . .
C23 C24 C25 C26 9.2(4) . .
O6 C24 C25 C27 14.0(4) . .
C23 C24 C25 C27 -168.4(3) . .
C22 C21 C26 C25 -2.2(4) . .
C17 C21 C26 C25 177.2(3) . .
C24 C25 C26 C21 -4.7(5) . .
C27 C25 C26 C21 172.8(3) . .
C26 C25 C27 C31 88.3(4) . .
C24 C25 C27 C31 -94.3(3) . .
C26 C25 C27 C28 -41.4(4) . .
C24 C25 C27 C28 136.1(3) . .
C31 C27 C28 C29 166.0(3) . .
C25 C27 C28 C29 -64.5(4) . .
C25 C27 C31 C32 95.6(3) . .
C28 C27 C31 C32 -135.6(3) . .
C25 C27 C31 C36 -83.1(3) . .
C28 C27 C31 C36 45.8(4) . .
C36 C31 C32 O7 177.0(3) . .
C27 C31 C32 O7 -1.8(4) . .
C36 C31 C32 C33 -2.9(4) . .
C27 C31 C32 C33 178.4(3) . .
O7 C32 C33 C34 -176.8(3) . .
C31 C32 C33 C34 3.1(5) . .
O7 C32 C33 C40 1.2(5) . .
C31 C32 C33 C40 -178.9(3) . .
C32 C33 C34 O8 178.8(3) . .
C40 C33 C34 O8 0.7(4) . .
C32 C33 C34 C35 -2.0(5) . .
C40 C33 C34 C35 179.9(3) . .
O8 C34 C35 C36 180.0(3) . .
C33 C34 C35 C36 0.8(5) . .
O8 C34 C35 C37 -2.4(5) . .
C33 C34 C35 C37 178.4(3) . .
C34 C35 C36 C31 -0.7(4) . .
C37 C35 C36 C31 -178.3(3) . .
C32 C31 C36 C35 1.7(4) . .
C27 C31 C36 C35 -179.6(3) . .
C2 C1 C37 C35 89.9(3) . .
C6 C1 C37 C35 -91.0(3) . .
C2 C1 C37 C38 -141.2(3) . .
C6 C1 C37 C38 37.9(4) . .
C36 C35 C37 C1 85.6(3) . .
C34 C35 C37 C1 -91.9(4) . .
C36 C35 C37 C38 -43.2(4) . .
C34 C35 C37 C38 139.3(3) . .
C1 C37 C38 C39 161.8(3) . .
C35 C37 C38 C39 -70.7(4) . .
C42 N1 C41 C42 -56.5(4) 2_665 .
C43 N1 C41 C42 -178.1(3) . .
N1 C41 C42 N1 58.5(4) . 2_665
C45 N2 C44 C45 58.5(4) . 2
C46 N2 C44 C45 -178.7(3) . 2
C44 N2 C45 C44 -58.8(4) . 2
C46 N2 C45 C44 178.1(3) . 2
C49 N3 C47 C48 179.1(3) . .
C48 N3 C47 C48 56.8(5) 2_876 .
N3 C47 C48 N3 -57.9(5) . 2_876
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198108
