#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/01/1520105.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_1520105
loop_
_publ_author_name
'Kelong Zhu'
'Christopher A. O'Keefe'
'V. Nicholas Vukotic'
'Robert W. Schurko'
'Stephen J. Loeb'
_publ_section_title
;
 A molecular shuttle that operates inside a metal-organic framework
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              514
_journal_page_last               519
_journal_paper_doi               10.1038/nchem.2258
_journal_volume                  7
_journal_year                    2015
_chemical_formula_moiety         'C52 H38 N4 O8, C16 H32 O8, C4 H10 O2'
_chemical_formula_sum            'C72 H80 N4 O18'
_chemical_formula_weight         1289.40
_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   geom
_cell_angle_alpha                106.0735(15)
_cell_angle_beta                 101.0732(16)
_cell_angle_gamma                92.4060(16)
_cell_formula_units_Z            2
_cell_length_a                   12.6007(4)
_cell_length_b                   16.0006(5)
_cell_length_c                   17.3353(5)
_cell_measurement_temperature    173(2)
_cell_volume                     3279.14(18)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48851
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.083
_diffrn_reflns_theta_min         2.714
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.774
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     853
_refine_ls_number_reflns         10914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0771
_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)+(0.1018P)²+4.6836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2207
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7653
_reflns_number_total             10914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nchem.2258-s2.cif
_cod_data_source_block           MIM_LINKER_4
_cod_database_code               1520105
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,
 H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B),
 C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B),
  C65(H65A,H65B), C66(H66A,H66B), C2S(H2SA,H2SB), C3S(H3SA,H3SB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C25(H25), C26(H26), C28(H28), C29(H29), C34(H34),
  C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C46(H46), C47(H47),
 C49(H49), C50(H50)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C52(H52A,H52B,
 H52C), C1C(H1CA,H1CB,H1CC), C4S(H4SA,H4SB,H4SC)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.9851(2) -0.7362(2) -0.22082(18) 0.0565(8) Uani 1 1 d . . . . .
O2 O 1.8553(2) -0.77038(18) -0.33579(15) 0.0448(7) Uani 1 1 d . . . . .
O3 O 0.91119(18) -0.53047(16) 0.11925(14) 0.0351(6) Uani 1 1 d . . . . .
O4 O 1.03424(19) -0.47740(16) 0.23732(14) 0.0379(6) Uani 1 1 d . . . . .
O5 O 1.8182(2) -0.2090(2) -0.5770(2) 0.0662(9) Uani 1 1 d . . . . .
O6 O 1.6974(2) -0.2190(2) -0.69307(17) 0.0568(8) Uani 1 1 d . . . . .
O7 O 0.8216(3) 0.0445(3) -0.1614(2) 0.0848(12) Uani 1 1 d . . . . .
O8 O 0.7247(2) 0.0251(2) -0.28762(18) 0.0557(8) Uani 1 1 d . . . . .
N1 N 1.4547(2) -0.55814(16) -0.17367(15) 0.0231(6) Uani 1 1 d . . . . .
N2 N 1.3168(2) -0.52446(16) -0.11037(15) 0.0228(6) Uani 1 1 d . . . . .
H2 H 1.2571 -0.5017 -0.0993 0.027 Uiso 1 1 calc R U . . .
N3 N 1.3726(2) -0.23007(17) -0.37961(16) 0.0254(6) Uani 1 1 d . . . . .
H3 H 1.4278 -0.2583 -0.3934 0.031 Uiso 1 1 calc R U . . .
N4 N 1.2282(2) -0.19572(17) -0.32274(16) 0.0271(6) Uani 1 1 d . . . . .
C1 C 1.9360(3) -0.7941(3) -0.3852(3) 0.0533(11) Uani 1 1 d . . . . .
H1A H 1.9766 -0.8393 -0.3685 0.080 Uiso 1 1 calc R U . . .
H1B H 1.9861 -0.7424 -0.3772 0.080 Uiso 1 1 calc R U . . .
H1C H 1.8998 -0.8165 -0.4433 0.080 Uiso 1 1 calc R U . . .
C2 C 1.8909(3) -0.7420(2) -0.2548(2) 0.0366(8) Uani 1 1 d . . . . .
C3 C 1.8007(3) -0.7183(2) -0.2112(2) 0.0298(7) Uani 1 1 d . . . . .
C4 C 1.6979(3) -0.7117(2) -0.2535(2) 0.0305(8) Uani 1 1 d . . . . .
H4 H 1.6841 -0.7232 -0.3115 0.037 Uiso 1 1 calc R U . . .
C5 C 1.6154(3) -0.6886(2) -0.21248(19) 0.0273(7) Uani 1 1 d . . . . .
H5 H 1.5454 -0.6845 -0.2427 0.033 Uiso 1 1 calc R U . . .
C6 C 1.6327(3) -0.6711(2) -0.12729(19) 0.0254(7) Uani 1 1 d . . . . .
C7 C 1.7364(3) -0.6784(2) -0.0855(2) 0.0323(8) Uani 1 1 d . . . . .
H7 H 1.7502 -0.6676 -0.0276 0.039 Uiso 1 1 calc R U . . .
C8 C 1.8197(3) -0.7011(2) -0.1266(2) 0.0351(8) Uani 1 1 d . . . . .
H8 H 1.8900 -0.7048 -0.0967 0.042 Uiso 1 1 calc R U . . .
C9 C 1.5429(2) -0.64694(19) -0.08415(19) 0.0235(7) Uani 1 1 d . . . . .
C10 C 1.4618(2) -0.5978(2) -0.11155(18) 0.0223(7) Uani 1 1 d . . . . .
C11 C 1.3754(2) -0.57737(19) -0.07096(19) 0.0225(7) Uani 1 1 d . . . . .
C12 C 1.3650(2) -0.6027(2) -0.00147(19) 0.0244(7) Uani 1 1 d . . . . .
C13 C 1.4482(3) -0.6485(2) 0.0261(2) 0.0273(7) Uani 1 1 d . . . . .
H13 H 1.4468 -0.6655 0.0742 0.033 Uiso 1 1 calc R U . . .
C14 C 1.5337(3) -0.6707(2) -0.01389(19) 0.0273(7) Uani 1 1 d . . . . .
H14 H 1.5875 -0.7030 0.0075 0.033 Uiso 1 1 calc R U . . .
C15 C 1.2733(3) -0.5815(2) 0.03993(19) 0.0252(7) Uani 1 1 d . . . . .
C16 C 1.1663(3) -0.5957(2) -0.0052(2) 0.0279(7) Uani 1 1 d . . . . .
H16 H 1.1523 -0.6196 -0.0632 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0806(3) -0.5751(2) 0.0336(2) 0.0302(8) Uani 1 1 d . . . . .
H17 H 1.0083 -0.5855 0.0021 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0996(3) -0.5396(2) 0.11802(19) 0.0258(7) Uani 1 1 d . . . . .
C19 C 1.2058(3) -0.5259(2) 0.1637(2) 0.0287(7) Uani 1 1 d . . . . .
H19 H 1.2195 -0.5018 0.2217 0.034 Uiso 1 1 calc R U . . .
C20 C 1.2912(3) -0.5471(2) 0.1253(2) 0.0281(7) Uani 1 1 d . . . . .
H20 H 1.3632 -0.5381 0.1572 0.034 Uiso 1 1 calc R U . . .
C21 C 1.0052(3) -0.5157(2) 0.1566(2) 0.0299(8) Uani 1 1 d . . . . .
C22 C 0.9465(3) -0.4540(3) 0.2789(2) 0.0503(11) Uani 1 1 d . . . . .
H22A H 0.9762 -0.4250 0.3373 0.075 Uiso 1 1 calc R U . . .
H22B H 0.8997 -0.5069 0.2729 0.075 Uiso 1 1 calc R U . . .
H22C H 0.9038 -0.4143 0.2546 0.075 Uiso 1 1 calc R U . . .
C23 C 1.3695(2) -0.51421(19) -0.17019(18) 0.0214(7) Uani 1 1 d . . . . .
C24 C 1.3419(2) -0.45224(19) -0.21702(18) 0.0214(7) Uani 1 1 d . . . . .
C25 C 1.3816(3) -0.4589(2) -0.2881(2) 0.0294(8) Uani 1 1 d . . . . .
H25 H 1.4183 -0.5080 -0.3095 0.035 Uiso 1 1 calc R U . . .
C26 C 1.3680(3) -0.3948(2) -0.3279(2) 0.0307(8) Uani 1 1 d . . . . .
H26 H 1.3948 -0.4003 -0.3765 0.037 Uiso 1 1 calc R U . . .
C27 C 1.3150(2) -0.3223(2) -0.29668(19) 0.0237(7) Uani 1 1 d . . . . .
C28 C 1.2722(2) -0.3171(2) -0.22757(19) 0.0250(7) Uani 1 1 d . . . . .
H28 H 1.2334 -0.2690 -0.2072 0.030 Uiso 1 1 calc R U . . .
C29 C 1.2857(2) -0.3811(2) -0.18843(19) 0.0255(7) Uani 1 1 d . . . . .
H29 H 1.2561 -0.3766 -0.1412 0.031 Uiso 1 1 calc R U . . .
C30 C 1.3045(2) -0.2496(2) -0.33282(18) 0.0235(7) Uani 1 1 d . . . . .
C31 C 1.7807(4) -0.2434(4) -0.7398(3) 0.0803(17) Uani 1 1 d . . . . .
H31A H 1.7470 -0.2649 -0.7985 0.120 Uiso 1 1 calc R U . . .
H31B H 1.8189 -0.2895 -0.7227 0.120 Uiso 1 1 calc R U . . .
H31C H 1.8326 -0.1923 -0.7300 0.120 Uiso 1 1 calc R U . . .
C32 C 1.7277(3) -0.2037(2) -0.6121(3) 0.0415(9) Uani 1 1 d . . . . .
C33 C 1.6369(3) -0.1777(2) -0.5701(2) 0.0332(8) Uani 1 1 d . . . . .
C34 C 1.5398(3) -0.1577(2) -0.6118(2) 0.0340(8) Uani 1 1 d . . . . .
H34 H 1.5314 -0.1600 -0.6680 0.041 Uiso 1 1 calc R U . . .
C35 C 1.4561(3) -0.1348(2) -0.5723(2) 0.0318(8) Uani 1 1 d . . . . .
H35 H 1.3904 -0.1213 -0.6015 0.038 Uiso 1 1 calc R U . . .
C36 C 1.4665(3) -0.1311(2) -0.4899(2) 0.0281(7) Uani 1 1 d . . . . .
C37 C 1.5648(3) -0.1499(2) -0.4479(2) 0.0336(8) Uani 1 1 d . . . . .
H37 H 1.5733 -0.1480 -0.3918 0.040 Uiso 1 1 calc R U . . .
C38 C 1.6496(3) -0.1712(2) -0.4874(2) 0.0359(8) Uani 1 1 d . . . . .
H38 H 1.7169 -0.1815 -0.4577 0.043 Uiso 1 1 calc R U . . .
C39 C 1.3730(3) -0.1108(2) -0.4507(2) 0.0287(7) Uani 1 1 d . . . . .
C40 C 1.3090(3) -0.0447(2) -0.4639(2) 0.0330(8) Uani 1 1 d . . . . .
H40 H 1.3282 -0.0117 -0.4980 0.040 Uiso 1 1 calc R U . . .
C41 C 1.2192(3) -0.0250(2) -0.4298(2) 0.0321(8) Uani 1 1 d . . . . .
H41 H 1.1795 0.0208 -0.4414 0.039 Uiso 1 1 calc R U . . .
C42 C 1.1847(3) -0.0697(2) -0.3793(2) 0.0298(8) Uani 1 1 d . . . . .
C43 C 1.2465(3) -0.1371(2) -0.36582(19) 0.0261(7) Uani 1 1 d . . . . .
C44 C 1.3373(2) -0.1571(2) -0.40093(19) 0.0250(7) Uani 1 1 d . . . . .
C45 C 1.0884(3) -0.0480(2) -0.3432(2) 0.0305(8) Uani 1 1 d . . . . .
C46 C 0.9914(3) -0.0367(3) -0.3912(2) 0.0405(9) Uani 1 1 d . . . . .
H46 H 0.9861 -0.0449 -0.4482 0.049 Uiso 1 1 calc R U . . .
C47 C 0.9032(3) -0.0138(3) -0.3572(2) 0.0439(9) Uani 1 1 d . . . . .
H47 H 0.8373 -0.0069 -0.3911 0.053 Uiso 1 1 calc R U . . .
C48 C 0.9094(3) -0.0006(2) -0.2739(2) 0.0361(8) Uani 1 1 d . . . . .
C49 C 1.0057(3) -0.0132(3) -0.2265(2) 0.0462(10) Uani 1 1 d . . . . .
H49 H 1.0109 -0.0046 -0.1694 0.055 Uiso 1 1 calc R U . . .
C50 C 1.0935(3) -0.0376(3) -0.2602(2) 0.0406(9) Uani 1 1 d . . . . .
H50 H 1.1581 -0.0474 -0.2268 0.049 Uiso 1 1 calc R U . . .
C51 C 0.8165(4) 0.0258(3) -0.2340(3) 0.0480(10) Uani 1 1 d . . . . .
C52 C 0.6321(4) 0.0477(4) -0.2516(3) 0.0696(15) Uani 1 1 d . . . . .
H52A H 0.5665 0.0373 -0.2952 0.104 Uiso 1 1 calc R U . . .
H52B H 0.6430 0.1095 -0.2197 0.104 Uiso 1 1 calc R U . . .
H52C H 0.6237 0.0116 -0.2154 0.104 Uiso 1 1 calc R U . . .
O9 O 1.6056(2) -0.25584(19) -0.27689(17) 0.0534(7) Uani 1 1 d . . . . .
O10 O 1.3385(2) -0.42187(19) -0.54589(18) 0.0574(8) Uani 1 1 d . . . . .
O11 O 1.5390(2) -0.35500(18) -0.44112(15) 0.0462(7) Uani 1 1 d . . . . .
O12 O 1.0663(3) -0.3860(3) -0.5222(2) 0.0890(12) Uani 1 1 d . . . . .
O13 O 1.4771(2) -0.16798(18) -0.10974(16) 0.0526(7) Uani 1 1 d . . . . .
O14 O 0.9083(3) -0.3273(2) -0.3649(2) 0.0733(10) Uani 1 1 d . . . . .
O15 O 1.2663(3) -0.1744(2) -0.06413(19) 0.0655(9) Uani 1 1 d . . . . .
O16 O 1.0480(2) -0.21274(19) -0.15862(18) 0.0571(8) Uani 1 1 d . . . . .
C1A C 1.0362(5) -0.3778(4) -0.4429(4) 0.099(2) Uani 1 1 d . . . . .
H1AA H 1.0167 -0.4362 -0.4374 0.118 Uiso 1 1 calc R U . . .
H1AB H 1.0972 -0.3474 -0.3969 0.118 Uiso 1 1 calc R U . . .
C1B C 0.9452(6) -0.3282(5) -0.4427(4) 0.102(2) Uani 1 1 d . . . . .
H1BA H 0.8866 -0.3557 -0.4914 0.122 Uiso 1 1 calc R U . . .
H1BB H 0.9663 -0.2679 -0.4429 0.122 Uiso 1 1 calc R U . . .
C53 C 0.9579(4) -0.2555(3) -0.2973(3) 0.0564(11) Uani 1 1 d . . . . .
H53A H 0.9079 -0.2093 -0.2895 0.068 Uiso 1 1 calc R U . . .
H53B H 1.0249 -0.2311 -0.3085 0.068 Uiso 1 1 calc R U . . .
C54 C 0.9856(3) -0.2835(3) -0.2208(3) 0.0549(11) Uani 1 1 d . . . . .
H54A H 0.9183 -0.2995 -0.2044 0.066 Uiso 1 1 calc R U . . .
H54B H 1.0275 -0.3350 -0.2305 0.066 Uiso 1 1 calc R U . . .
C55 C 1.0841(4) -0.2322(3) -0.0831(3) 0.0555(11) Uani 1 1 d . . . . .
H55A H 1.1128 -0.2900 -0.0935 0.067 Uiso 1 1 calc R U . . .
H55B H 1.0230 -0.2336 -0.0550 0.067 Uiso 1 1 calc R U . . .
C56 C 1.1708(4) -0.1629(3) -0.0313(3) 0.0605(12) Uani 1 1 d . . . . .
H56A H 1.1468 -0.1046 -0.0305 0.073 Uiso 1 1 calc R U . . .
H56B H 1.1862 -0.1666 0.0258 0.073 Uiso 1 1 calc R U . . .
C57 C 1.3494(4) -0.1049(3) -0.0285(3) 0.0668(13) Uani 1 1 d . . . . .
H57A H 1.3980 -0.1159 0.0190 0.080 Uiso 1 1 calc R U . . .
H57B H 1.3171 -0.0497 -0.0085 0.080 Uiso 1 1 calc R U . . .
C58 C 1.4128(4) -0.0967(3) -0.0904(3) 0.0624(13) Uani 1 1 d . . . . .
H58A H 1.3623 -0.0947 -0.1411 0.075 Uiso 1 1 calc R U . . .
H58B H 1.4609 -0.0412 -0.0689 0.075 Uiso 1 1 calc R U . . .
C59 C 1.5357(4) -0.1616(3) -0.1698(3) 0.0568(12) Uani 1 1 d . . . . .
H59A H 1.5930 -0.1118 -0.1469 0.068 Uiso 1 1 calc R U . . .
H59B H 1.4862 -0.1516 -0.2175 0.068 Uiso 1 1 calc R U . . .
C60 C 1.5866(4) -0.2464(3) -0.1967(2) 0.0545(11) Uani 1 1 d . . . . .
H60A H 1.6560 -0.2448 -0.1579 0.065 Uiso 1 1 calc R U . . .
H60B H 1.5372 -0.2964 -0.1973 0.065 Uiso 1 1 calc R U . . .
C61 C 1.6486(3) -0.3359(3) -0.3077(3) 0.0537(11) Uani 1 1 d . . . . .
H61A H 1.6043 -0.3845 -0.3003 0.064 Uiso 1 1 calc R U . . .
H61B H 1.7239 -0.3338 -0.2769 0.064 Uiso 1 1 calc R U . . .
C62 C 1.6481(3) -0.3514(3) -0.3966(3) 0.0518(11) Uani 1 1 d . . . . .
H62A H 1.6938 -0.3036 -0.4040 0.062 Uiso 1 1 calc R U . . .
H62B H 1.6786 -0.4071 -0.4178 0.062 Uiso 1 1 calc R U . . .
C63 C 1.5292(4) -0.3925(3) -0.5269(2) 0.0489(10) Uani 1 1 d . . . . .
H63A H 1.5366 -0.4559 -0.5392 0.059 Uiso 1 1 calc R U . . .
H63B H 1.5872 -0.3650 -0.5458 0.059 Uiso 1 1 calc R U . . .
C64 C 1.4212(4) -0.3778(3) -0.5695(2) 0.0545(12) Uani 1 1 d . . . . .
H64A H 1.4130 -0.3144 -0.5551 0.065 Uiso 1 1 calc R U . . .
H64B H 1.4144 -0.3999 -0.6297 0.065 Uiso 1 1 calc R U . . .
C65 C 1.2370(4) -0.3911(4) -0.5637(3) 0.0751(15) Uani 1 1 d . . . . .
H65A H 1.2073 -0.4111 -0.6237 0.090 Uiso 1 1 calc R U . . .
H65B H 1.2449 -0.3263 -0.5457 0.090 Uiso 1 1 calc R U . . .
C66 C 1.1650(4) -0.4230(5) -0.5223(4) 0.098(2) Uani 1 1 d . . . . .
H66A H 1.1488 -0.4869 -0.5477 0.118 Uiso 1 1 calc R U . . .
H66B H 1.2030 -0.4134 -0.4645 0.118 Uiso 1 1 calc R U . . .
O1S O 1.7831(3) -0.0895(2) 0.0047(3) 0.0984(14) Uani 1 1 d . . . . .
O2S O 1.6892(3) -0.0791(2) 0.1469(2) 0.0773(10) Uani 1 1 d . . . . .
C1C C 1.8656(5) -0.0945(4) -0.0389(4) 0.100(2) Uani 1 1 d . . . . .
H1CA H 1.9359 -0.0913 -0.0018 0.150 Uiso 1 1 calc R U . . .
H1CB H 1.8655 -0.0457 -0.0629 0.150 Uiso 1 1 calc R U . . .
H1CC H 1.8536 -0.1499 -0.0829 0.150 Uiso 1 1 calc R U . . .
C2S C 1.7725(4) -0.1556(3) 0.0397(4) 0.0707(14) Uani 1 1 d . . . . .
H2SA H 1.8401 -0.1538 0.0804 0.085 Uiso 1 1 calc R U . . .
H2SB H 1.7630 -0.2124 -0.0034 0.085 Uiso 1 1 calc R U . . .
C3S C 1.6798(5) -0.1494(4) 0.0805(4) 0.0790(16) Uani 1 1 d . . . . .
H3SA H 1.6132 -0.1477 0.0401 0.095 Uiso 1 1 calc R U . . .
H3SB H 1.6703 -0.2029 0.0975 0.095 Uiso 1 1 calc R U . . .
C4S C 1.6067(4) -0.0777(4) 0.1909(3) 0.0745(15) Uani 1 1 d . . . . .
H4SA H 1.6239 -0.0281 0.2409 0.112 Uiso 1 1 calc R U . . .
H4SB H 1.6011 -0.1323 0.2058 0.112 Uiso 1 1 calc R U . . .
H4SC H 1.5374 -0.0717 0.1569 0.112 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O2 C1 117.0(3) . .
C21 O4 C22 115.7(3) . .
C32 O6 C31 116.3(3) . .
C51 O8 C52 114.8(3) . .
C23 N1 C10 105.5(2) . .
C23 N2 C11 106.9(2) . .
C30 N3 C44 106.3(2) . .
C30 N4 C43 104.9(3) . .
O1 C2 O2 124.0(3) . .
O1 C2 C3 124.2(3) . .
O2 C2 C3 111.8(3) . .
C4 C3 C2 121.2(3) . .
C4 C3 C8 119.0(3) . .
C8 C3 C2 119.8(3) . .
C5 C4 C3 120.8(3) . .
C4 C5 C6 121.2(3) . .
C5 C6 C9 120.6(3) . .
C7 C6 C5 117.5(3) . .
C7 C6 C9 122.0(3) . .
C8 C7 C6 121.4(3) . .
C7 C8 C3 120.2(3) . .
C10 C9 C6 121.6(3) . .
C14 C9 C6 122.5(3) . .
C14 C9 C10 115.9(3) . .
N1 C10 C9 129.2(3) . .
N1 C10 C11 109.9(3) . .
C9 C10 C11 120.8(3) . .
N2 C11 C10 105.0(3) . .
N2 C11 C12 131.5(3) . .
C12 C11 C10 123.3(3) . .
C11 C12 C15 122.6(3) . .
C13 C12 C11 114.8(3) . .
C13 C12 C15 122.6(3) . .
C12 C13 C14 123.0(3) . .
C9 C14 C13 122.2(3) . .
C16 C15 C12 120.8(3) . .
C16 C15 C20 118.3(3) . .
C20 C15 C12 120.9(3) . .
C17 C16 C15 120.8(3) . .
C16 C17 C18 120.4(3) . .
C17 C18 C19 119.3(3) . .
C17 C18 C21 118.4(3) . .
C19 C18 C21 122.3(3) . .
C20 C19 C18 120.4(3) . .
C19 C20 C15 120.8(3) . .
O3 C21 O4 123.2(3) . .
O3 C21 C18 124.0(3) . .
O4 C21 C18 112.9(3) . .
N1 C23 N2 112.7(3) . .
N1 C23 C24 123.5(3) . .
N2 C23 C24 123.4(3) . .
C25 C24 C23 119.7(3) . .
C29 C24 C23 121.5(3) . .
C29 C24 C25 118.5(3) . .
C26 C25 C24 120.7(3) . .
C25 C26 C27 120.1(3) . .
C26 C27 C30 122.6(3) . .
C28 C27 C26 119.3(3) . .
C28 C27 C30 118.1(3) . .
C29 C28 C27 120.4(3) . .
C28 C29 C24 121.0(3) . .
N3 C30 C27 123.7(3) . .
N4 C30 N3 113.3(3) . .
N4 C30 C27 123.0(3) . .
O5 C32 O6 124.1(4) . .
O5 C32 C33 124.0(4) . .
O6 C32 C33 111.9(3) . .
C34 C33 C32 121.2(3) . .
C38 C33 C32 119.6(3) . .
C38 C33 C34 119.2(3) . .
C35 C34 C33 120.5(3) . .
C34 C35 C36 120.8(3) . .
C35 C36 C37 118.5(3) . .
C35 C36 C39 119.3(3) . .
C37 C36 C39 122.2(3) . .
C38 C37 C36 120.6(3) . .
C37 C38 C33 120.3(3) . .
C40 C39 C36 121.4(3) . .
C40 C39 C44 114.4(3) . .
C44 C39 C36 124.1(3) . .
C41 C40 C39 123.1(3) . .
C40 C41 C42 122.7(3) . .
C41 C42 C43 115.4(3) . .
C41 C42 C45 122.1(3) . .
C43 C42 C45 122.5(3) . .
N4 C43 C42 128.4(3) . .
N4 C43 C44 109.7(3) . .
C42 C43 C44 121.7(3) . .
N3 C44 C39 131.5(3) . .
N3 C44 C43 105.7(3) . .
C39 C44 C43 122.6(3) . .
C46 C45 C42 120.9(3) . .
C46 C45 C50 118.5(3) . .
C50 C45 C42 120.6(3) . .
C47 C46 C45 120.9(3) . .
C46 C47 C48 120.5(4) . .
C47 C48 C51 122.5(3) . .
C49 C48 C47 118.4(3) . .
C49 C48 C51 119.1(3) . .
C50 C49 C48 121.4(3) . .
C49 C50 C45 120.1(3) . .
O7 C51 O8 122.6(4) . .
O7 C51 C48 124.3(4) . .
O8 C51 C48 113.1(3) . .
C61 O9 C60 111.4(3) . .
C65 O10 C64 112.7(4) . .
C63 O11 C62 111.8(3) . .
C66 O12 C1A 109.1(4) . .
C59 O13 C58 111.9(3) . .
C53 O14 C1B 113.1(4) . .
C57 O15 C56 114.5(3) . .
C54 O16 C55 113.4(3) . .
C1B C1A O12 105.7(5) . .
C1A C1B O14 105.3(5) . .
O14 C53 C54 110.4(4) . .
O16 C54 C53 107.7(4) . .
O16 C55 C56 107.8(4) . .
O15 C56 C55 108.9(3) . .
O15 C57 C58 109.7(4) . .
O13 C58 C57 111.7(4) . .
O13 C59 C60 108.4(3) . .
O9 C60 C59 108.2(3) . .
O9 C61 C62 109.9(3) . .
O11 C62 C61 109.6(3) . .
O11 C63 C64 108.3(3) . .
O10 C64 C63 109.7(3) . .
O10 C65 C66 109.4(4) . .
O12 C66 C65 116.3(5) . .
C2S O1S C1C 115.4(4) . .
C3S O2S C4S 115.0(4) . .
O1S C2S C3S 112.6(4) . .
O2S C3S C2S 114.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.206(4) .
O2 C1 1.448(4) .
O2 C2 1.329(4) .
O3 C21 1.214(4) .
O4 C21 1.333(4) .
O4 C22 1.440(4) .
O5 C32 1.204(5) .
O6 C31 1.448(5) .
O6 C32 1.330(5) .
O7 C51 1.198(5) .
O8 C51 1.335(5) .
O8 C52 1.440(5) .
N1 C10 1.385(4) .
N1 C23 1.310(4) .
N2 C11 1.382(4) .
N2 C23 1.376(4) .
N3 C30 1.370(4) .
N3 C44 1.385(4) .
N4 C30 1.322(4) .
N4 C43 1.388(4) .
C2 C3 1.488(5) .
C3 C4 1.385(5) .
C3 C8 1.386(5) .
C4 C5 1.376(4) .
C5 C6 1.396(4) .
C6 C7 1.394(5) .
C6 C9 1.479(4) .
C7 C8 1.384(5) .
C9 C10 1.406(4) .
C9 C14 1.396(4) .
C10 C11 1.408(4) .
C11 C12 1.400(4) .
C12 C13 1.389(4) .
C12 C15 1.477(4) .
C13 C14 1.397(4) .
C15 C16 1.397(5) .
C15 C20 1.397(4) .
C16 C17 1.383(4) .
C17 C18 1.384(5) .
C18 C19 1.392(4) .
C18 C21 1.487(4) .
C19 C20 1.377(4) .
C23 C24 1.459(4) .
C24 C25 1.396(4) .
C24 C29 1.391(4) .
C25 C26 1.385(5) .
C26 C27 1.393(4) .
C27 C28 1.389(4) .
C27 C30 1.466(4) .
C28 C29 1.376(4) .
C32 C33 1.485(5) .
C33 C34 1.395(5) .
C33 C38 1.385(5) .
C34 C35 1.373(5) .
C35 C36 1.394(5) .
C36 C37 1.400(5) .
C36 C39 1.474(5) .
C37 C38 1.382(5) .
C39 C40 1.399(5) .
C39 C44 1.403(4) .
C40 C41 1.383(5) .
C41 C42 1.391(5) .
C42 C43 1.401(5) .
C42 C45 1.480(5) .
C43 C44 1.404(4) .
C45 C46 1.389(5) .
C45 C50 1.391(5) .
C46 C47 1.372(5) .
C47 C48 1.387(5) .
C48 C49 1.384(5) .
C48 C51 1.489(5) .
C49 C50 1.370(5) .
O9 C60 1.424(5) .
O9 C61 1.417(5) .
O10 C64 1.418(5) .
O10 C65 1.400(5) .
O11 C62 1.431(5) .
O11 C63 1.419(4) .
O12 C1A 1.469(7) .
O12 C66 1.398(7) .
O13 C58 1.428(5) .
O13 C59 1.411(5) .
O14 C1B 1.506(7) .
O14 C53 1.413(5) .
O15 C56 1.425(5) .
O15 C57 1.410(6) .
O16 C54 1.409(5) .
O16 C55 1.423(5) .
C1A C1B 1.421(8) .
C53 C54 1.498(6) .
C55 C56 1.482(7) .
C57 C58 1.485(7) .
C59 C60 1.519(6) .
C61 C62 1.489(6) .
C63 C64 1.481(6) .
C65 C66 1.419(7) .
O1S C1C 1.391(6) .
O1S C2S 1.369(6) .
O2S C3S 1.350(6) .
O2S C4S 1.400(6) .
C2S C3S 1.472(7) .
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 H2 O3 0.88 2.19 3.027(3) 159.2 2_745
N3 H3 O11 0.88 2.23 3.092(4) 167.1 .
C22 H22A O12 0.98 2.38 3.338(6) 166.6 1_556
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C2 C3 C4 168.5(4) . . . .
O1 C2 C3 C8 -10.4(6) . . . .
O2 C2 C3 C4 -11.5(5) . . . .
O2 C2 C3 C8 169.6(3) . . . .
O5 C32 C33 C34 168.5(4) . . . .
O5 C32 C33 C38 -10.0(6) . . . .
O6 C32 C33 C34 -10.5(5) . . . .
O6 C32 C33 C38 171.0(3) . . . .
N1 C10 C11 N2 -0.1(3) . . . .
N1 C10 C11 C12 -175.2(3) . . . .
N1 C23 C24 C25 22.6(5) . . . .
N1 C23 C24 C29 -151.0(3) . . . .
N2 C11 C12 C13 -172.4(3) . . . .
N2 C11 C12 C15 6.9(5) . . . .
N2 C23 C24 C25 -165.8(3) . . . .
N2 C23 C24 C29 20.6(5) . . . .
N4 C43 C44 N3 1.1(3) . . . .
N4 C43 C44 C39 177.6(3) . . . .
C1 O2 C2 O1 -1.1(6) . . . .
C1 O2 C2 C3 178.9(3) . . . .
C2 C3 C4 C5 -179.1(3) . . . .
C2 C3 C8 C7 179.6(3) . . . .
C3 C4 C5 C6 0.1(5) . . . .
C4 C3 C8 C7 0.6(5) . . . .
C4 C5 C6 C7 -0.4(5) . . . .
C4 C5 C6 C9 -179.6(3) . . . .
C5 C6 C7 C8 0.8(5) . . . .
C5 C6 C9 C10 -33.8(4) . . . .
C5 C6 C9 C14 146.6(3) . . . .
C6 C7 C8 C3 -0.9(5) . . . .
C6 C9 C10 N1 -6.4(5) . . . .
C6 C9 C10 C11 178.4(3) . . . .
C6 C9 C14 C13 -179.3(3) . . . .
C7 C6 C9 C10 147.1(3) . . . .
C7 C6 C9 C14 -32.5(5) . . . .
C8 C3 C4 C5 -0.2(5) . . . .
C9 C6 C7 C8 180.0(3) . . . .
C9 C10 C11 N2 176.0(3) . . . .
C9 C10 C11 C12 0.9(5) . . . .
C10 N1 C23 N2 -1.9(3) . . . .
C10 N1 C23 C24 170.5(3) . . . .
C10 C9 C14 C13 1.1(5) . . . .
C10 C11 C12 C13 1.3(4) . . . .
C10 C11 C12 C15 -179.3(3) . . . .
C11 N2 C23 N1 1.9(3) . . . .
C11 N2 C23 C24 -170.5(3) . . . .
C11 C12 C13 C14 -2.3(5) . . . .
C11 C12 C15 C16 47.3(4) . . . .
C11 C12 C15 C20 -132.8(3) . . . .
C12 C13 C14 C9 1.2(5) . . . .
C12 C15 C16 C17 -179.5(3) . . . .
C12 C15 C20 C19 178.8(3) . . . .
C13 C12 C15 C16 -133.4(3) . . . .
C13 C12 C15 C20 46.5(4) . . . .
C14 C9 C10 N1 173.2(3) . . . .
C14 C9 C10 C11 -2.1(4) . . . .
C15 C12 C13 C14 178.4(3) . . . .
C15 C16 C17 C18 0.4(5) . . . .
C16 C15 C20 C19 -1.3(5) . . . .
C16 C17 C18 C19 -1.0(5) . . . .
C16 C17 C18 C21 177.9(3) . . . .
C17 C18 C19 C20 0.3(5) . . . .
C17 C18 C21 O3 4.8(5) . . . .
C17 C18 C21 O4 -176.2(3) . . . .
C18 C19 C20 C15 0.8(5) . . . .
C19 C18 C21 O3 -176.4(3) . . . .
C19 C18 C21 O4 2.6(4) . . . .
C20 C15 C16 C17 0.7(5) . . . .
C21 C18 C19 C20 -178.5(3) . . . .
C22 O4 C21 O3 0.1(5) . . . .
C22 O4 C21 C18 -178.9(3) . . . .
C23 N1 C10 C9 -174.5(3) . . . .
C23 N1 C10 C11 1.2(3) . . . .
C23 N2 C11 C10 -1.0(3) . . . .
C23 N2 C11 C12 173.6(3) . . . .
C23 C24 C25 C26 -171.9(3) . . . .
C23 C24 C29 C28 171.6(3) . . . .
C24 C25 C26 C27 0.5(5) . . . .
C25 C24 C29 C28 -2.1(5) . . . .
C25 C26 C27 C28 -2.7(5) . . . .
C25 C26 C27 C30 175.8(3) . . . .
C26 C27 C28 C29 2.6(5) . . . .
C26 C27 C30 N3 -22.9(5) . . . .
C26 C27 C30 N4 157.6(3) . . . .
C27 C28 C29 C24 -0.1(5) . . . .
C28 C27 C30 N3 155.7(3) . . . .
C28 C27 C30 N4 -23.8(5) . . . .
C29 C24 C25 C26 1.9(5) . . . .
C30 N3 C44 C39 -177.0(3) . . . .
C30 N3 C44 C43 -0.9(3) . . . .
C30 N4 C43 C42 175.7(3) . . . .
C30 N4 C43 C44 -0.8(3) . . . .
C30 C27 C28 C29 -176.1(3) . . . .
C31 O6 C32 O5 0.0(6) . . . .
C31 O6 C32 C33 179.0(4) . . . .
C32 C33 C34 C35 179.2(3) . . . .
C32 C33 C38 C37 -177.9(3) . . . .
C33 C34 C35 C36 0.0(5) . . . .
C34 C33 C38 C37 3.5(5) . . . .
C34 C35 C36 C37 1.0(5) . . . .
C34 C35 C36 C39 -176.8(3) . . . .
C35 C36 C37 C38 0.3(5) . . . .
C35 C36 C39 C40 -43.1(5) . . . .
C35 C36 C39 C44 133.8(3) . . . .
C36 C37 C38 C33 -2.6(5) . . . .
C36 C39 C40 C41 178.5(3) . . . .
C36 C39 C44 N3 -3.2(6) . . . .
C36 C39 C44 C43 -178.7(3) . . . .
C37 C36 C39 C40 139.2(3) . . . .
C37 C36 C39 C44 -43.8(5) . . . .
C38 C33 C34 C35 -2.2(5) . . . .
C39 C36 C37 C38 178.0(3) . . . .
C39 C40 C41 C42 -0.1(5) . . . .
C40 C39 C44 N3 174.0(3) . . . .
C40 C39 C44 C43 -1.5(5) . . . .
C40 C41 C42 C43 -0.7(5) . . . .
C40 C41 C42 C45 -180.0(3) . . . .
C41 C42 C43 N4 -175.8(3) . . . .
C41 C42 C43 C44 0.4(5) . . . .
C41 C42 C45 C46 47.0(5) . . . .
C41 C42 C45 C50 -132.3(4) . . . .
C42 C43 C44 N3 -175.7(3) . . . .
C42 C43 C44 C39 0.8(5) . . . .
C42 C45 C46 C47 -177.9(3) . . . .
C42 C45 C50 C49 176.7(3) . . . .
C43 N4 C30 N3 0.3(4) . . . .
C43 N4 C30 C27 179.8(3) . . . .
C43 C42 C45 C46 -132.2(4) . . . .
C43 C42 C45 C50 48.5(5) . . . .
C44 N3 C30 N4 0.4(4) . . . .
C44 N3 C30 C27 -179.1(3) . . . .
C44 C39 C40 C41 1.2(5) . . . .
C45 C42 C43 N4 3.5(5) . . . .
C45 C42 C43 C44 179.6(3) . . . .
C45 C46 C47 C48 0.6(6) . . . .
C46 C45 C50 C49 -2.6(6) . . . .
C46 C47 C48 C49 -1.5(6) . . . .
C46 C47 C48 C51 178.9(4) . . . .
C47 C48 C49 C50 0.3(6) . . . .
C47 C48 C51 O7 -173.7(4) . . . .
C47 C48 C51 O8 7.5(5) . . . .
C48 C49 C50 C45 1.8(6) . . . .
C49 C48 C51 O7 6.7(6) . . . .
C49 C48 C51 O8 -172.1(4) . . . .
C50 C45 C46 C47 1.4(6) . . . .
C51 C48 C49 C50 179.9(4) . . . .
C52 O8 C51 O7 -0.7(6) . . . .
C52 O8 C51 C48 178.2(3) . . . .
O9 C61 C62 O11 -59.8(5) . . . .
O10 C65 C66 O12 169.3(5) . . . .
O11 C63 C64 O10 -63.2(4) . . . .
O12 C1A C1B O14 174.8(4) . . . .
O13 C59 C60 O9 156.2(3) . . . .
O14 C53 C54 O16 171.9(3) . . . .
O15 C57 C58 O13 -70.2(5) . . . .
O16 C55 C56 O15 -72.3(4) . . . .
C1A O12 C66 C65 -143.5(6) . . . .
C1B O14 C53 C54 -140.2(4) . . . .
C53 O14 C1B C1A 90.8(6) . . . .
C54 O16 C55 C56 165.3(3) . . . .
C55 O16 C54 C53 -177.2(3) . . . .
C56 O15 C57 C58 -149.0(4) . . . .
C57 O15 C56 C55 170.3(4) . . . .
C58 O13 C59 C60 -170.9(3) . . . .
C59 O13 C58 C57 178.7(3) . . . .
C60 O9 C61 C62 169.5(3) . . . .
C61 O9 C60 C59 -177.2(3) . . . .
C62 O11 C63 C64 -168.8(3) . . . .
C63 O11 C62 C61 -164.1(3) . . . .
C64 O10 C65 C66 -166.8(5) . . . .
C65 O10 C64 C63 162.3(4) . . . .
C66 O12 C1A C1B 171.4(5) . . . .
O1S C2S C3S O2S -66.1(7) . . . .
C1C O1S C2S C3S -176.5(5) . . . .
C4S O2S C3S C2S -173.6(5) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045391
