#------------------------------------------------------------------------------
#$Date: 2025-07-06 18:13:56 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/04/7250457.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_7250457
loop_
_publ_author_name
'Steenhaut, Timothy'
'Li, Xiao'
'Zhou, Fuli'
'Robeyns, Koen'
'Leyssens, Tom'
'Filinchuk, Yaroslav'
'Shemchuk, Oleksii'
_publ_section_title
;
 A hydrogen-bonded organic framework with ultramicroporous channels based
 on proline and dl-2-phenoxypropionic acid
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3887
_journal_page_last               3890
_journal_paper_doi               10.1039/D5CE00357A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C9 H10 O3, C5 H9 N O2 [+ solvent]'
_chemical_formula_sum            'C14 H19 N O5'
_chemical_formula_weight         281.30
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            54
_cell_length_a                   62.932(2)
_cell_length_b                   62.932(2)
_cell_length_c                   5.69893(15)
_cell_measurement_reflns_used    5181
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.0700
_cell_measurement_theta_min      2.9450
_cell_volume                     19546.4(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'155 images, ΔΦ 0.75° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       75
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_k_max       55
_diffrn_reflns_limit_k_min       -75
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            26916
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.235
_diffrn_reflns_theta_max         25.235
_diffrn_reflns_theta_min         2.822
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       needle
_exptl_crystal_F_000             8100
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7814
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0795
_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)+(0.0355P)²+75.0472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5089
_reflns_number_total             7814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00357a2.cif
_cod_data_source_block           alex_A153_AA22
_cod_depositor_comments
'Adding full bibliography for 7250457--7250458.cif.'
_cod_original_cell_volume        19546.7(14)
_cod_database_code               7250457
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N1 N 0.49947(5) 0.41256(5) -0.0719(4) 0.0347(7) Uani 1 1 d . . . . .
H1A H 0.507507 0.404906 -0.028580 0.042 Uiso 1 1 calc R U . . .
H1B H 0.490399 0.404911 -0.197114 0.042 Uiso 1 1 calc R U . . .
C2 C 0.51723(8) 0.43856(7) -0.1307(7) 0.0558(11) Uani 1 1 d . . . . .
H2A H 0.532433 0.444242 -0.044788 0.067 Uiso 1 1 calc R U . A 1
H2B H 0.520834 0.440351 -0.297387 0.067 Uiso 1 1 calc R U . A 1
C3 C 0.50539(13) 0.45236(11) -0.0628(14) 0.0478(16) Uani 0.683(10) 1 d . . P B 1
H3A H 0.495174 0.452624 -0.188918 0.057 Uiso 0.683(10) 1 calc R U P B 1
H3B H 0.517470 0.469109 -0.022287 0.057 Uiso 0.683(10) 1 calc R U P B 1
C3B C 0.5115(3) 0.4523(3) 0.055(3) 0.0478(16) Uani 0.317(10) 1 d . . P B 2
H3C H 0.523983 0.457973 0.175762 0.057 Uiso 0.317(10) 1 calc R U P B 2
H3D H 0.512088 0.466564 -0.016487 0.057 Uiso 0.317(10) 1 calc R U P B 2
C4 C 0.48975(9) 0.43860(7) 0.1518(7) 0.0549(11) Uani 1 1 d . . . . .
H4A H 0.498915 0.445480 0.295501 0.066 Uiso 1 1 calc R U . B 1
H4B H 0.474958 0.439766 0.156952 0.066 Uiso 1 1 calc R U . B 1
C5 C 0.48332(6) 0.41195(6) 0.1244(5) 0.0299(8) Uani 1 1 d . . . . .
H5 H 0.465990 0.401637 0.082119 0.036 Uiso 1 1 calc R U . . .
C6 C 0.48912(6) 0.40231(6) 0.3442(5) 0.0299(8) Uani 1 1 d . . . . .
O7 O 0.50820(5) 0.40168(5) 0.3529(4) 0.0434(6) Uani 1 1 d . . . . .
O8 O 0.47384(4) 0.39682(4) 0.5120(4) 0.0372(6) Uani 1 1 d . . . . .
N11 N 0.45130(5) 0.34199(5) 0.6090(5) 0.0386(7) Uani 1 1 d . . . . .
H11A H 0.457854 0.339280 0.482175 0.046 Uiso 1 1 calc R U . . .
H11B H 0.460977 0.357457 0.654310 0.046 Uiso 1 1 calc R U . . .
C12 C 0.42621(8) 0.33764(8) 0.5542(7) 0.0583(11) Uani 1 1 d . . . . .
H12A H 0.422260 0.347908 0.650445 0.070 Uiso 1 1 calc R U . . .
H12B H 0.424862 0.340896 0.390101 0.070 Uiso 1 1 calc R U . . .
C13 C 0.41013(8) 0.31161(9) 0.6095(8) 0.0630(12) Uani 1 1 d . . . . .
H13A H 0.409911 0.301301 0.481902 0.076 Uiso 1 1 calc R U . . .
H13B H 0.393502 0.308065 0.639385 0.076 Uiso 1 1 calc R U . . .
C14 C 0.42128(7) 0.30759(8) 0.8269(7) 0.0584(12) Uani 1 1 d . . . . .
H14A H 0.417478 0.290664 0.837118 0.070 Uiso 1 1 calc R U . . .
H14B H 0.415179 0.311583 0.966599 0.070 Uiso 1 1 calc R U . . .
C15 C 0.44905(7) 0.32492(6) 0.8004(5) 0.0374(8) Uani 1 1 d . . . . .
H15 H 0.457147 0.315668 0.755707 0.045 Uiso 1 1 calc R U . . .
C16 C 0.46033(6) 0.33940(7) 1.0230(6) 0.0366(8) Uani 1 1 d . . . . .
O17 O 0.46364(5) 0.36029(5) 1.0379(4) 0.0562(8) Uani 1 1 d . . . . .
O18 O 0.46475(5) 0.32827(4) 1.1862(4) 0.0458(7) Uani 1 1 d . . . . .
N21 N 0.52147(5) 0.36439(5) 0.2623(4) 0.0362(7) Uani 1 1 d . . . . .
H21A H 0.505886 0.357667 0.307333 0.043 Uiso 1 1 calc R U . . .
H21B H 0.523826 0.374226 0.140971 0.043 Uiso 1 1 calc R U . . .
C22 C 0.52699(9) 0.34492(7) 0.1931(7) 0.0575(12) Uani 1 1 d . . . . .
H22A H 0.515694 0.329455 0.267579 0.069 Uiso 1 1 calc R U . . .
H22B H 0.525861 0.342650 0.024246 0.069 Uiso 1 1 calc R U . . .
C23 C 0.55203(10) 0.35381(9) 0.2740(9) 0.0745(14) Uani 1 1 d . . . . .
H23A H 0.563738 0.364233 0.156173 0.089 Uiso 1 1 calc R U . . .
H23B H 0.554667 0.340163 0.305952 0.089 Uiso 1 1 calc R U . . .
C24 C 0.55486(8) 0.36782(8) 0.4900(7) 0.0529(11) Uani 1 1 d . . . . .
H24A H 0.571782 0.380712 0.509697 0.063 Uiso 1 1 calc R U . . .
H24B H 0.550002 0.357137 0.626023 0.063 Uiso 1 1 calc R U . . .
C25 C 0.53810(6) 0.37878(6) 0.4601(5) 0.0311(8) Uani 1 1 d . . . . .
H25 H 0.547783 0.396166 0.417750 0.037 Uiso 1 1 calc R U . . .
C26 C 0.52320(6) 0.37567(6) 0.6795(5) 0.0311(8) Uani 1 1 d . . . . .
O27 O 0.50244(4) 0.35776(5) 0.6915(4) 0.0462(7) Uani 1 1 d . . . . .
O28 O 0.53405(4) 0.39125(4) 0.8423(4) 0.0370(6) Uani 1 1 d . . . . .
C31 C 0.36812(7) 0.34845(7) 0.7044(6) 0.0448(10) Uani 1 1 d . . . . .
H31 H 0.359235 0.345407 0.565921 0.054 Uiso 1 1 calc R U . . .
C32 C 0.36307(7) 0.32960(7) 0.8560(7) 0.0516(10) Uani 1 1 d . . . . .
H32 H 0.350675 0.313769 0.820394 0.062 Uiso 1 1 calc R U . . .
C33 C 0.37622(8) 0.33396(8) 1.0605(7) 0.0549(11) Uani 1 1 d . . . . .
H33 H 0.372832 0.321129 1.162656 0.066 Uiso 1 1 calc R U . . .
C34 C 0.39417(7) 0.35710(7) 1.1120(7) 0.0488(10) Uani 1 1 d . . . . .
H34 H 0.402935 0.359996 1.251030 0.059 Uiso 1 1 calc R U . . .
C35 C 0.39966(6) 0.37630(7) 0.9637(6) 0.0415(9) Uani 1 1 d . . . . .
H35 H 0.412105 0.392055 1.000885 0.050 Uiso 1 1 calc R U . . .
C36 C 0.38644(6) 0.37196(7) 0.7577(6) 0.0380(8) Uani 1 1 d . . . . .
O37 O 0.38947(4) 0.38957(5) 0.5980(4) 0.0504(7) Uani 1 1 d . . . . .
C38 C 0.40918(7) 0.41400(7) 0.6341(7) 0.0506(10) Uani 1 1 d . . . . .
H38 H 0.407678 0.419295 0.791902 0.061 Uiso 1 1 calc R U . . .
C39 C 0.40604(9) 0.42980(9) 0.4593(9) 0.0747(14) Uani 1 1 d . . . . .
H39A H 0.418734 0.446549 0.480588 0.112 Uiso 1 1 calc R U . . .
H39B H 0.390311 0.428513 0.480873 0.112 Uiso 1 1 calc R U . . .
H39C H 0.407062 0.424537 0.303674 0.112 Uiso 1 1 calc R U . . .
C40 C 0.43387(7) 0.41574(7) 0.6132(7) 0.0447(9) Uani 1 1 d . . . . .
O41 O 0.45146(6) 0.43178(6) 0.7076(7) 0.0895(12) Uani 1 1 d . . . . .
O42 O 0.43451(5) 0.39928(5) 0.4813(4) 0.0526(7) Uani 1 1 d . . . . .
H42 H 0.448500 0.401489 0.478986 0.079 Uiso 1 1 calc R U . . .
C51 C 0.36918(7) 0.20371(7) 1.1221(7) 0.0478(10) Uani 1 1 d . . . . .
H51 H 0.365974 0.194995 1.261771 0.057 Uiso 1 1 calc R U . . .
C52 C 0.35036(7) 0.19886(8) 0.9706(8) 0.0585(11) Uani 1 1 d . . . . .
H52 H 0.334442 0.186769 1.007792 0.070 Uiso 1 1 calc R U . . .
C53 C 0.35482(8) 0.21175(9) 0.7634(8) 0.0591(12) Uani 1 1 d . . . . .
H53 H 0.342050 0.208352 0.660304 0.071 Uiso 1 1 calc R U . . .
C54 C 0.37824(8) 0.22955(8) 0.7119(7) 0.0519(11) Uani 1 1 d . . . . .
H54 H 0.381336 0.238339 0.572733 0.062 Uiso 1 1 calc R U . . .
C55 C 0.39742(7) 0.23477(7) 0.8624(6) 0.0456(10) Uani 1 1 d . . . . .
H55 H 0.413277 0.247073 0.826331 0.055 Uiso 1 1 calc R U . . .
C56 C 0.39271(7) 0.22141(6) 1.0679(6) 0.0375(8) Uani 1 1 d . . . . .
O57 O 0.41034(4) 0.22397(4) 1.2265(4) 0.0446(6) Uani 1 1 d . . . . .
C58 C 0.43501(6) 0.24235(6) 1.1872(6) 0.0397(9) Uani 1 1 d . . . . .
H58 H 0.439525 0.241568 1.024142 0.048 Uiso 1 1 calc R U . . .
C59 C 0.45050(7) 0.23688(7) 1.3502(7) 0.0508(10) Uani 1 1 d . . . . .
H59A H 0.467482 0.248892 1.328443 0.076 Uiso 1 1 calc R U . . .
H59B H 0.448023 0.220850 1.316448 0.076 Uiso 1 1 calc R U . . .
H59C H 0.445854 0.237399 1.509636 0.076 Uiso 1 1 calc R U . . .
C60 C 0.43853(7) 0.26756(7) 1.2371(6) 0.0416(9) Uani 1 1 d . . . . .
O61 O 0.42614(7) 0.27137(5) 1.3676(6) 0.0863(11) Uani 1 1 d . . . . .
O62 O 0.45734(5) 0.28475(5) 1.1250(4) 0.0525(7) Uani 1 1 d . . . . .
H62 H 0.458767 0.298125 1.156343 0.079 Uiso 1 1 calc R U . . .
C71 C 0.6534(5) 0.4124(5) 0.829(4) 0.084(3) Uani 0.37(3) 1 d G U P C 3
H71 H 0.662524 0.418245 0.966294 0.100 Uiso 0.37(3) 1 calc R U P C 3
C72 C 0.6537(5) 0.3936(5) 0.704(4) 0.103(4) Uani 0.37(3) 1 d G U P C 3
H72 H 0.663069 0.386876 0.757454 0.123 Uiso 0.37(3) 1 calc R U P C 3
C73 C 0.6401(5) 0.3848(5) 0.499(4) 0.117(4) Uani 0.37(3) 1 d G U P C 3
H73 H 0.640289 0.372228 0.415442 0.140 Uiso 0.37(3) 1 calc R U P C 3
C74 C 0.6261(5) 0.3948(6) 0.419(5) 0.105(3) Uani 0.37(3) 1 d G U P C 3
H74 H 0.616965 0.388948 0.282267 0.126 Uiso 0.37(3) 1 calc R U P C 3
C75 C 0.6258(6) 0.4136(7) 0.544(8) 0.074(2) Uani 0.37(3) 1 d G U P C 3
H75 H 0.616420 0.420317 0.491103 0.089 Uiso 0.37(3) 1 calc R U P C 3
C76 C 0.6394(6) 0.4224(5) 0.749(7) 0.0622(15) Uani 0.37(3) 1 d G U P C 3
C71B C 0.6589(3) 0.4182(3) 0.823(3) 0.084(3) Uani 0.63(3) 1 d G . P C 4
H71B H 0.668315 0.425310 0.956071 0.100 Uiso 0.63(3) 1 calc R U P C 4
C72B C 0.6638(4) 0.4032(3) 0.680(2) 0.103(4) Uani 0.63(3) 1 d G . P C 4
H72B H 0.676466 0.400310 0.718244 0.123 Uiso 0.63(3) 1 calc R U P C 4
C73B C 0.6497(4) 0.3926(3) 0.481(2) 0.117(4) Uani 0.63(3) 1 d G . P C 4
H73B H 0.652946 0.382556 0.385457 0.140 Uiso 0.63(3) 1 calc R U P C 4
C74B C 0.6307(3) 0.3969(4) 0.424(3) 0.105(3) Uani 0.63(3) 1 d G . P C 4
H74B H 0.621274 0.389802 0.290494 0.126 Uiso 0.63(3) 1 calc R U P C 4
C75B C 0.6258(3) 0.4119(4) 0.566(4) 0.074(2) Uani 0.63(3) 1 d G . P C 4
H75B H 0.613123 0.414801 0.528317 0.089 Uiso 0.63(3) 1 calc R U P C 4
C76B C 0.6399(4) 0.4225(3) 0.766(4) 0.0622(15) Uani 0.63(3) 1 d G . P C 4
O77 O 0.63854(5) 0.43916(6) 0.9015(5) 0.0629(8) Uani 1 1 d . . . . .
C78 C 0.62066(7) 0.44588(7) 0.8525(7) 0.0508(10) Uani 1 1 d . . . . .
H78 H 0.621623 0.450412 0.686717 0.061 Uiso 1 1 calc R U . . .
C79 C 0.62683(7) 0.46777(8) 1.0032(7) 0.0597(12) Uani 1 1 d . . . . .
H79A H 0.615727 0.473650 0.968861 0.089 Uiso 1 1 calc R U . . .
H79B H 0.643342 0.480492 0.971469 0.089 Uiso 1 1 calc R U . . .
H79C H 0.625362 0.463179 1.165519 0.089 Uiso 1 1 calc R U . . .
C80 C 0.59510(7) 0.42507(8) 0.9073(7) 0.0492(10) Uani 1 1 d . . . . .
O81 O 0.59062(6) 0.41036(6) 1.0576(6) 0.0898(12) Uani 1 1 d . . . . .
O82 O 0.57843(5) 0.42641(5) 0.7826(4) 0.0523(7) Uani 1 1 d . . . . .
H82 H 0.565450 0.413372 0.791334 0.079 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
_geom_angle_publ_flag
C2 N1 C5 108.9(3) . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1B 109.9 . . ?
C5 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
C3 C2 N1 105.7(4) . . ?
N1 C2 C3B 102.0(6) . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
N1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 C4 104.5(5) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3B C2 112.7(11) . . ?
C4 C3B H3C 109.1 . . ?
C2 C3B H3C 109.1 . . ?
C4 C3B H3D 109.1 . . ?
C2 C3B H3D 109.1 . . ?
H3C C3B H3D 107.8 . . ?
C3B C4 C5 107.0(7) . . ?
C5 C4 C3 106.3(4) . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C6 109.3(3) . . ?
N1 C5 C4 104.2(3) . . ?
C6 C5 C4 111.8(3) . . ?
N1 C5 H5 110.5 . . ?
C6 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
O7 C6 O8 125.5(3) . . ?
O7 C6 C5 119.0(3) . . ?
O8 C6 C5 115.4(3) . . ?
C15 N11 C12 108.1(3) . . ?
C15 N11 H11A 110.1 . . ?
C12 N11 H11A 110.1 . . ?
C15 N11 H11B 110.1 . . ?
C12 N11 H11B 110.1 . . ?
H11A N11 H11B 108.4 . . ?
C13 C12 N11 103.6(3) . . ?
C13 C12 H12A 111.0 . . ?
N11 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
N11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C12 C13 C14 104.2(3) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C13 C14 C15 105.1(3) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
N11 C15 C16 109.4(3) . . ?
N11 C15 C14 104.4(3) . . ?
C16 C15 C14 111.7(3) . . ?
N11 C15 H15 110.4 . . ?
C16 C15 H15 110.4 . . ?
C14 C15 H15 110.4 . . ?
O17 C16 O18 124.8(3) . . ?
O17 C16 C15 118.7(3) . . ?
O18 C16 C15 116.4(3) . . ?
C22 N21 C25 108.6(3) . . ?
C22 N21 H21A 110.0 . . ?
C25 N21 H21A 110.0 . . ?
C22 N21 H21B 110.0 . . ?
C25 N21 H21B 110.0 . . ?
H21A N21 H21B 108.4 . . ?
C23 C22 N21 104.7(3) . . ?
C23 C22 H22A 110.8 . . ?
N21 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
N21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C22 C23 C24 106.2(4) . . ?
C22 C23 H23A 110.5 . . ?
C24 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
C24 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C23 C24 C25 105.8(3) . . ?
C23 C24 H24A 110.6 . . ?
C25 C24 H24A 110.6 . . ?
C23 C24 H24B 110.6 . . ?
C25 C24 H24B 110.6 . . ?
H24A C24 H24B 108.7 . . ?
N21 C25 C26 110.1(3) . . ?
N21 C25 C24 104.0(3) . . ?
C26 C25 C24 111.8(3) . . ?
N21 C25 H25 110.3 . . ?
C26 C25 H25 110.3 . . ?
C24 C25 H25 110.3 . . ?
O27 C26 O28 125.5(3) . . ?
O27 C26 C25 118.0(3) . . ?
O28 C26 C25 116.3(3) . . ?
C32 C31 C36 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C36 C31 H31 120.1 . . ?
C31 C32 C33 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 119.6(4) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 121.4(4) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C34 C35 C36 119.2(3) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
O37 C36 C31 115.1(3) . . ?
O37 C36 C35 125.2(3) . . ?
C31 C36 C35 119.7(3) . . ?
C36 O37 C38 118.0(3) . . ?
O37 C38 C39 106.8(3) . . ?
O37 C38 C40 112.1(3) . . ?
C39 C38 C40 112.0(3) . . ?
O37 C38 H38 108.6 . . ?
C39 C38 H38 108.6 . . ?
C40 C38 H38 108.6 . . ?
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 . . ?
O41 C40 O42 123.6(4) . . ?
O41 C40 C38 120.9(4) . . ?
O42 C40 C38 115.5(3) . . ?
C40 O42 H42 109.5 . . ?
C52 C51 C56 120.1(4) . . ?
C52 C51 H51 120.0 . . ?
C56 C51 H51 120.0 . . ?
C51 C52 C53 120.6(4) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C54 C53 C52 119.0(4) . . ?
C54 C53 H53 120.5 . . ?
C52 C53 H53 120.5 . . ?
C53 C54 C55 121.2(4) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C54 C55 C56 119.0(4) . . ?
C54 C55 H55 120.5 . . ?
C56 C55 H55 120.5 . . ?
C51 C56 O57 115.3(3) . . ?
C51 C56 C55 120.0(4) . . ?
O57 C56 C55 124.7(3) . . ?
C56 O57 C58 118.8(3) . . ?
O57 C58 C59 106.6(3) . . ?
O57 C58 C60 110.6(3) . . ?
C59 C58 C60 110.6(3) . . ?
O57 C58 H58 109.7 . . ?
C59 C58 H58 109.7 . . ?
C60 C58 H58 109.7 . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
O61 C60 O62 123.7(4) . . ?
O61 C60 C58 124.3(4) . . ?
O62 C60 C58 112.0(3) . . ?
C60 O62 H62 109.5 . . ?
C72 C71 C76 120.0 . . ?
C72 C71 H71 120.0 . . ?
C76 C71 H71 120.0 . . ?
C71 C72 C73 120.0 . . ?
C71 C72 H72 120.0 . . ?
C73 C72 H72 120.0 . . ?
C72 C73 C74 120.0 . . ?
C72 C73 H73 120.0 . . ?
C74 C73 H73 120.0 . . ?
C75 C74 C73 120.0 . . ?
C75 C74 H74 120.0 . . ?
C73 C74 H74 120.0 . . ?
C76 C75 C74 120.0 . . ?
C76 C75 H75 120.0 . . ?
C74 C75 H75 120.0 . . ?
O77 C76 C75 125(3) . . ?
O77 C76 C71 115(3) . . ?
C75 C76 C71 120.0 . . ?
C72B C71B C76B 120.0 . . ?
C72B C71B H71B 120.0 . . ?
C76B C71B H71B 120.0 . . ?
C71B C72B C73B 120.0 . . ?
C71B C72B H72B 120.0 . . ?
C73B C72B H72B 120.0 . . ?
C72B C73B C74B 120.0 . . ?
C72B C73B H73B 120.0 . . ?
C74B C73B H73B 120.0 . . ?
C75B C74B C73B 120.0 . . ?
C75B C74B H74B 120.0 . . ?
C73B C74B H74B 120.0 . . ?
C74B C75B C76B 120.0 . . ?
C74B C75B H75B 120.0 . . ?
C76B C75B H75B 120.0 . . ?
O77 C76B C75B 125.0(15) . . ?
O77 C76B C71B 114.6(15) . . ?
C75B C76B C71B 120.0 . . ?
C76B O77 C78 119.5(10) . . ?
C76 O77 C78 116.4(16) . . ?
O77 C78 C79 106.4(3) . . ?
O77 C78 C80 111.2(3) . . ?
C79 C78 C80 110.6(3) . . ?
O77 C78 H78 109.6 . . ?
C79 C78 H78 109.6 . . ?
C80 C78 H78 109.6 . . ?
C78 C79 H79A 109.5 . . ?
C78 C79 H79B 109.5 . . ?
H79A C79 H79B 109.5 . . ?
C78 C79 H79C 109.5 . . ?
H79A C79 H79C 109.5 . . ?
H79B C79 H79C 109.5 . . ?
O81 C80 O82 123.9(4) . . ?
O81 C80 C78 123.9(4) . . ?
O82 C80 C78 111.9(3) . . ?
C80 O82 H82 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
N1 C2 1.487(4) . ?
N1 C5 1.499(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.451(8) . ?
C2 C3B 1.517(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3B C4 1.320(16) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4 C5 1.524(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.514(4) . ?
C5 H5 0.9800 . ?
C6 O7 1.222(4) . ?
C6 O8 1.275(4) . ?
N11 C15 1.487(4) . ?
N11 C12 1.495(5) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
C12 C13 1.466(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.536(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.516(5) . ?
C15 H15 0.9800 . ?
C16 O17 1.226(4) . ?
C16 O18 1.276(4) . ?
N21 C22 1.484(5) . ?
N21 C25 1.496(4) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
C22 C23 1.459(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.472(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.531(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.516(4) . ?
C25 H25 0.9800 . ?
C26 O27 1.229(4) . ?
C26 O28 1.272(4) . ?
C31 C32 1.370(5) . ?
C31 C36 1.381(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.355(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.384(5) . ?
C35 H35 0.9300 . ?
C36 O37 1.372(4) . ?
O37 C38 1.427(4) . ?
C38 C39 1.489(5) . ?
C38 C40 1.507(5) . ?
C38 H38 0.9800 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 O41 1.190(4) . ?
C40 O42 1.296(4) . ?
O42 H42 0.8200 . ?
C51 C52 1.371(5) . ?
C51 C56 1.371(5) . ?
C51 H51 0.9300 . ?
C52 C53 1.379(6) . ?
C52 H52 0.9300 . ?
C53 C54 1.365(6) . ?
C53 H53 0.9300 . ?
C54 C55 1.380(5) . ?
C54 H54 0.9300 . ?
C55 C56 1.385(5) . ?
C55 H55 0.9300 . ?
C56 O57 1.376(4) . ?
O57 C58 1.415(4) . ?
C58 C59 1.506(5) . ?
C58 C60 1.515(5) . ?
C58 H58 0.9800 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 O61 1.186(4) . ?
C60 O62 1.304(4) . ?
O62 H62 0.8200 . ?
C71 C72 1.3900 . ?
C71 C76 1.3900 . ?
C71 H71 0.9300 . ?
C72 C73 1.3900 . ?
C72 H72 0.9300 . ?
C73 C74 1.3900 . ?
C73 H73 0.9300 . ?
C74 C75 1.3900 . ?
C74 H74 0.9300 . ?
C75 C76 1.3900 . ?
C75 H75 0.9300 . ?
C76 O77 1.39(3) . ?
C71B C72B 1.3900 . ?
C71B C76B 1.3900 . ?
C71B H71B 0.9300 . ?
C72B C73B 1.3900 . ?
C72B H72B 0.9300 . ?
C73B C74B 1.3900 . ?
C73B H73B 0.9300 . ?
C74B C75B 1.3900 . ?
C74B H74B 0.9300 . ?
C75B C76B 1.3900 . ?
C75B H75B 0.9300 . ?
C76B O77 1.338(14) . ?
O77 C78 1.414(5) . ?
C78 C79 1.500(6) . ?
C78 C80 1.514(5) . ?
C78 H78 0.9800 . ?
C79 H79A 0.9600 . ?
C79 H79B 0.9600 . ?
C79 H79C 0.9600 . ?
C80 O81 1.187(5) . ?
C80 O82 1.304(4) . ?
O82 H82 0.8200 . ?
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
_geom_torsion_publ_flag
C5 N1 C2 C3 -26.5(5) . . . . ?
C5 N1 C2 C3B 4.3(8) . . . . ?
N1 C2 C3 C4 32.7(6) . . . . ?
N1 C2 C3B C4 -18.6(14) . . . . ?
C2 C3B C4 C5 24.6(14) . . . . ?
C2 C3 C4 C5 -27.6(6) . . . . ?
C2 N1 C5 C6 -111.1(3) . . . . ?
C2 N1 C5 C4 8.6(4) . . . . ?
C3B C4 C5 N1 -20.2(9) . . . . ?
C3 C4 C5 N1 11.4(5) . . . . ?
C3B C4 C5 C6 97.8(9) . . . . ?
C3 C4 C5 C6 129.3(4) . . . . ?
N1 C5 C6 O7 15.8(4) . . . . ?
C4 C5 C6 O7 -99.0(4) . . . . ?
N1 C5 C6 O8 -168.2(3) . . . . ?
C4 C5 C6 O8 77.0(4) . . . . ?
C15 N11 C12 C13 -29.8(4) . . . . ?
N11 C12 C13 C14 38.5(4) . . . . ?
C12 C13 C14 C15 -33.3(5) . . . . ?
C12 N11 C15 C16 -110.6(3) . . . . ?
C12 N11 C15 C14 9.0(4) . . . . ?
C13 C14 C15 N11 14.6(4) . . . . ?
C13 C14 C15 C16 132.8(4) . . . . ?
N11 C15 C16 O17 18.0(5) . . . . ?
C14 C15 C16 O17 -97.1(4) . . . . ?
N11 C15 C16 O18 -164.8(3) . . . . ?
C14 C15 C16 O18 80.1(4) . . . . ?
C25 N21 C22 C23 -22.8(4) . . . . ?
N21 C22 C23 C24 33.0(5) . . . . ?
C22 C23 C24 C25 -30.8(5) . . . . ?
C22 N21 C25 C26 -115.9(3) . . . . ?
C22 N21 C25 C24 4.0(4) . . . . ?
C23 C24 C25 N21 16.1(4) . . . . ?
C23 C24 C25 C26 134.8(4) . . . . ?
N21 C25 C26 O27 20.7(4) . . . . ?
C24 C25 C26 O27 -94.4(4) . . . . ?
N21 C25 C26 O28 -163.5(3) . . . . ?
C24 C25 C26 O28 81.5(4) . . . . ?
C36 C31 C32 C33 -0.3(6) . . . . ?
C31 C32 C33 C34 0.4(6) . . . . ?
C32 C33 C34 C35 -0.5(6) . . . . ?
C33 C34 C35 C36 0.5(6) . . . . ?
C32 C31 C36 O37 -178.0(3) . . . . ?
C32 C31 C36 C35 0.3(5) . . . . ?
C34 C35 C36 O37 177.7(3) . . . . ?
C34 C35 C36 C31 -0.4(5) . . . . ?
C31 C36 O37 C38 -175.8(3) . . . . ?
C35 C36 O37 C38 6.0(5) . . . . ?
C36 O37 C38 C39 -171.8(3) . . . . ?
C36 O37 C38 C40 65.2(4) . . . . ?
O37 C38 C40 O41 -155.7(4) . . . . ?
C39 C38 C40 O41 84.3(5) . . . . ?
O37 C38 C40 O42 26.5(5) . . . . ?
C39 C38 C40 O42 -93.5(4) . . . . ?
C56 C51 C52 C53 -0.4(6) . . . . ?
C51 C52 C53 C54 -0.4(7) . . . . ?
C52 C53 C54 C55 0.3(6) . . . . ?
C53 C54 C55 C56 0.8(6) . . . . ?
C52 C51 C56 O57 -177.0(3) . . . . ?
C52 C51 C56 C55 1.4(6) . . . . ?
C54 C55 C56 C51 -1.6(5) . . . . ?
C54 C55 C56 O57 176.6(3) . . . . ?
C51 C56 O57 C58 -178.1(3) . . . . ?
C55 C56 O57 C58 3.6(5) . . . . ?
C56 O57 C58 C59 -166.5(3) . . . . ?
C56 O57 C58 C60 73.2(4) . . . . ?
O57 C58 C60 O61 25.8(5) . . . . ?
C59 C58 C60 O61 -92.1(5) . . . . ?
O57 C58 C60 O62 -156.2(3) . . . . ?
C59 C58 C60 O62 85.9(4) . . . . ?
C76 C71 C72 C73 0.0 . . . . ?
C71 C72 C73 C74 0.0 . . . . ?
C72 C73 C74 C75 0.0 . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 O77 -173(3) . . . . ?
C74 C75 C76 C71 0.0 . . . . ?
C72 C71 C76 O77 174(3) . . . . ?
C72 C71 C76 C75 0.0 . . . . ?
C76B C71B C72B C73B 0.0 . . . . ?
C71B C72B C73B C74B 0.0 . . . . ?
C72B C73B C74B C75B 0.0 . . . . ?
C73B C74B C75B C76B 0.0 . . . . ?
C74B C75B C76B O77 172.7(18) . . . . ?
C74B C75B C76B C71B 0.0 . . . . ?
C72B C71B C76B O77 -173.5(16) . . . . ?
C72B C71B C76B C75B 0.0 . . . . ?
C75B C76B O77 C78 3.9(14) . . . . ?
C71B C76B O77 C78 177.0(7) . . . . ?
C75 C76 O77 C78 6(2) . . . . ?
C71 C76 O77 C78 -167.1(12) . . . . ?
C76B O77 C78 C79 -169.6(11) . . . . ?
C76 O77 C78 C79 -167.7(17) . . . . ?
C76B O77 C78 C80 69.9(11) . . . . ?
C76 O77 C78 C80 71.8(18) . . . . ?
O77 C78 C80 O81 31.0(6) . . . . ?
C79 C78 C80 O81 -86.9(5) . . . . ?
O77 C78 C80 O82 -154.1(3) . . . . ?
C79 C78 C80 O82 87.9(4) . . . . ?
