#------------------------------------------------------------------------------
#$Date: 2025-07-06 18:13:56 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/04/7250458.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_7250458
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-2019/3
_audit_update_record
;
2024-10-25 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                   62.5573(16)
_cell_length_b                   62.5573(16)
_cell_length_c                   5.66980(14)
_cell_measurement_reflns_used    6713
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.7980
_cell_measurement_theta_min      2.3210
_cell_volume                     19215.6(8)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'154 images, ΔΦ 0.5° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_h_min       -79
_diffrn_reflns_limit_k_max       76
_diffrn_reflns_limit_k_min       -79
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21261
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.830
_diffrn_reflns_theta_min         2.256
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94415
_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    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             8100
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         9116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0419P)²+31.1434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6355
_reflns_number_total             9116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00357a2.cif
_cod_data_source_block           Alex_HOF_150k
_cod_depositor_comments
'Adding full bibliography for 7250457--7250458.cif.'
_cod_original_cell_volume        19215.6(11)
_cod_database_code               7250458
_shelx_shelxl_version_number     2019/3
_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 0.50081(3) 0.41339(3) -0.0652(2) 0.0187(3) Uani 1 1 d . . . . .
H1A H 0.508824 0.405255 -0.020863 0.022 Uiso 1 1 calc R U . . .
H1B H 0.491367 0.405638 -0.193665 0.022 Uiso 1 1 calc R U . . .
C2 C 0.51917(4) 0.43975(4) -0.1242(3) 0.0260(5) Uani 1 1 d . . . . .
H2A H 0.523328 0.441658 -0.294217 0.031 Uiso 1 1 calc R U . . .
H2B H 0.534510 0.445704 -0.031237 0.031 Uiso 1 1 calc R U . . .
C3 C 0.50594(4) 0.45343(4) -0.0583(3) 0.0273(5) Uani 1 1 d . . . . .
H3A H 0.494249 0.451952 -0.183590 0.033 Uiso 1 1 calc R U . . .
H3B H 0.517778 0.471123 -0.029835 0.033 Uiso 1 1 calc R U . . .
C4 C 0.49228(4) 0.44064(4) 0.1675(3) 0.0265(5) Uani 1 1 d . . . . .
H4A H 0.477520 0.442385 0.189025 0.032 Uiso 1 1 calc R U . . .
H4B H 0.503161 0.447712 0.306574 0.032 Uiso 1 1 calc R U . . .
C5 C 0.48480(3) 0.41332(3) 0.1335(3) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.466977 0.403389 0.088987 0.021 Uiso 1 1 calc R U . . .
C6 C 0.48983(3) 0.40277(3) 0.3546(3) 0.0169(4) Uani 1 1 d . . . . .
O7 O 0.50889(2) 0.40157(2) 0.3656(2) 0.0231(3) Uani 1 1 d . . . . .
O8 O 0.47418(2) 0.39730(2) 0.5225(2) 0.0201(3) Uani 1 1 d . . . . .
N11 N 0.45126(3) 0.34265(3) 0.6164(3) 0.0205(4) Uani 1 1 d . . . . .
H11A H 0.461007 0.358588 0.662943 0.025 Uiso 1 1 calc R U . . .
H11B H 0.458244 0.339939 0.487399 0.025 Uiso 1 1 calc R U . . .
C12 C 0.42583(4) 0.33790(4) 0.5574(4) 0.0291(5) Uani 1 1 d . . . . .
H12A H 0.424527 0.341055 0.388404 0.035 Uiso 1 1 calc R U . . .
H12B H 0.421471 0.348348 0.654085 0.035 Uiso 1 1 calc R U . . .
C13 C 0.40956(4) 0.31094(4) 0.6164(4) 0.0290(5) Uani 1 1 d . . . . .
H13A H 0.410091 0.300282 0.490198 0.035 Uiso 1 1 calc R U . . .
H13B H 0.392244 0.306815 0.641156 0.035 Uiso 1 1 calc R U . . .
C14 C 0.42090(4) 0.30818(4) 0.8440(3) 0.0269(5) Uani 1 1 d . . . . .
H14A H 0.416928 0.290876 0.866248 0.032 Uiso 1 1 calc R U . . .
H14B H 0.414772 0.313244 0.981845 0.032 Uiso 1 1 calc R U . . .
C15 C 0.44890(3) 0.32539(3) 0.8122(3) 0.0184(4) Uani 1 1 d . . . . .
H15 H 0.456937 0.315639 0.766216 0.022 Uiso 1 1 calc R U . . .
C16 C 0.46097(3) 0.34044(3) 1.0345(3) 0.0190(4) Uani 1 1 d . . . . .
O17 O 0.46396(3) 0.36138(2) 1.0497(2) 0.0280(3) Uani 1 1 d . . . . .
O18 O 0.46587(2) 0.32937(2) 1.1987(2) 0.0232(3) Uani 1 1 d . . . . .
N21 N 0.52176(3) 0.36378(3) 0.2699(2) 0.0197(3) Uani 1 1 d . . . . .
H21A H 0.505715 0.356581 0.316439 0.024 Uiso 1 1 calc R U . . .
H21B H 0.523993 0.373948 0.146150 0.024 Uiso 1 1 calc R U . . .
C22 C 0.52781(4) 0.34438(4) 0.1973(3) 0.0274(5) Uani 1 1 d . . . . .
H22A H 0.526067 0.341691 0.024612 0.033 Uiso 1 1 calc R U . . .
H22B H 0.516943 0.328537 0.278063 0.033 Uiso 1 1 calc R U . . .
C23 C 0.55435(4) 0.35485(4) 0.2730(4) 0.0301(5) Uani 1 1 d . . . . .
H23A H 0.565822 0.367074 0.157407 0.036 Uiso 1 1 calc R U . . .
H23B H 0.558534 0.341642 0.292775 0.036 Uiso 1 1 calc R U . . .
C24 C 0.55520(4) 0.36707(4) 0.5082(3) 0.0258(4) Uani 1 1 d . . . . .
H24A H 0.572280 0.380004 0.546892 0.031 Uiso 1 1 calc R U . . .
H24B H 0.548796 0.354743 0.637094 0.031 Uiso 1 1 calc R U . . .
C25 C 0.53854(3) 0.37841(3) 0.4711(3) 0.0176(4) Uani 1 1 d . . . . .
H25 H 0.548700 0.396217 0.426787 0.021 Uiso 1 1 calc R U . . .
C26 C 0.52324(3) 0.37554(3) 0.6905(3) 0.0169(4) Uani 1 1 d . . . . .
O27 O 0.50218(2) 0.35744(2) 0.7030(2) 0.0235(3) Uani 1 1 d . . . . .
O28 O 0.53415(2) 0.39153(2) 0.8544(2) 0.0202(3) Uani 1 1 d . . . . .
C31 C 0.36771(3) 0.34778(4) 0.7095(3) 0.0234(4) Uani 1 1 d . . . . .
H31 H 0.358576 0.344451 0.567112 0.028 Uiso 1 1 calc R U . . .
C32 C 0.36285(4) 0.32885(4) 0.8649(3) 0.0269(5) Uani 1 1 d . . . . .
H32 H 0.350255 0.312488 0.829354 0.032 Uiso 1 1 calc R U . . .
C33 C 0.37626(4) 0.33359(4) 1.0731(4) 0.0281(5) Uani 1 1 d . . . . .
H33 H 0.372917 0.320546 1.179437 0.034 Uiso 1 1 calc R U . . .
C34 C 0.39446(4) 0.35740(4) 1.1237(3) 0.0254(4) Uani 1 1 d . . . . .
H34 H 0.403569 0.360661 1.266108 0.030 Uiso 1 1 calc R U . . .
C35 C 0.39969(3) 0.37665(4) 0.9705(3) 0.0222(4) Uani 1 1 d . . . . .
H35 H 0.412374 0.392967 1.006363 0.027 Uiso 1 1 calc R U . . .
C36 C 0.38606(3) 0.37172(3) 0.7628(3) 0.0208(4) Uani 1 1 d . . . . .
O37 O 0.38901(2) 0.38946(2) 0.6011(2) 0.0255(3) Uani 1 1 d . . . . .
C38 C 0.40854(4) 0.41420(4) 0.6420(4) 0.0260(4) Uani 1 1 d . . . . .
H38 H 0.406559 0.419506 0.803055 0.031 Uiso 1 1 calc R U . . .
C39 C 0.40549(4) 0.43017(4) 0.4598(4) 0.0365(5) Uani 1 1 d . . . . .
H39A H 0.418364 0.447422 0.482086 0.055 Uiso 1 1 calc R U . . .
H39B H 0.389221 0.428688 0.477949 0.055 Uiso 1 1 calc R U . . .
H39C H 0.406904 0.424730 0.301377 0.055 Uiso 1 1 calc R U . . .
C40 C 0.43388(4) 0.41639(4) 0.6241(3) 0.0248(4) Uani 1 1 d . . . . .
O41 O 0.45119(3) 0.43202(3) 0.7313(3) 0.0506(5) Uani 1 1 d . . . . .
O42 O 0.43486(2) 0.40031(3) 0.4824(2) 0.0278(3) Uani 1 1 d . . . . .
H42 H 0.449303 0.402643 0.480492 0.042 Uiso 1 1 calc R U . . .
C51 C 0.36921(4) 0.20382(4) 1.1460(3) 0.0223(4) Uani 1 1 d . . . . .
H51 H 0.366064 0.194989 1.290060 0.027 Uiso 1 1 calc R U . . .
C52 C 0.34994(4) 0.19900(4) 0.9947(4) 0.0272(5) Uani 1 1 d . . . . .
H52 H 0.333570 0.186866 1.035915 0.033 Uiso 1 1 calc R U . . .
C53 C 0.35431(4) 0.21176(4) 0.7829(4) 0.0285(5) Uani 1 1 d . . . . .
H53 H 0.341090 0.208199 0.678069 0.034 Uiso 1 1 calc R U . . .
C54 C 0.37818(4) 0.22970(4) 0.7273(3) 0.0270(5) Uani 1 1 d . . . . .
H54 H 0.381242 0.238645 0.584043 0.032 Uiso 1 1 calc R U . . .
C55 C 0.39780(4) 0.23488(4) 0.8774(3) 0.0229(4) Uani 1 1 d . . . . .
H55 H 0.414108 0.247291 0.837692 0.027 Uiso 1 1 calc R U . . .
C56 C 0.39318(3) 0.22162(3) 1.0864(3) 0.0194(4) Uani 1 1 d . . . . .
O57 O 0.41117(2) 0.22400(2) 1.2435(2) 0.0216(3) Uani 1 1 d . . . . .
C58 C 0.43598(3) 0.24269(3) 1.1981(3) 0.0204(4) Uani 1 1 d . . . . .
H58 H 0.440220 0.241800 1.029672 0.024 Uiso 1 1 calc R U . . .
C59 C 0.45231(4) 0.23750(4) 1.3594(3) 0.0249(4) Uani 1 1 d . . . . .
H59A H 0.469676 0.249590 1.329074 0.037 Uiso 1 1 calc R U . . .
H59B H 0.449412 0.220844 1.328743 0.037 Uiso 1 1 calc R U . . .
H59C H 0.448341 0.238734 1.524278 0.037 Uiso 1 1 calc R U . . .
C60 C 0.43956(4) 0.26824(4) 1.2497(3) 0.0206(4) Uani 1 1 d . . . . .
O61 O 0.42723(3) 0.27191(3) 1.3888(3) 0.0410(4) Uani 1 1 d . . . . .
O62 O 0.45828(3) 0.28561(2) 1.1301(2) 0.0261(3) Uani 1 1 d . . . . .
H62 H 0.459803 0.299417 1.162117 0.039 Uiso 1 1 calc R U . . .
C71 C 0.65755(3) 0.41597(3) 0.8282(3) 0.0507(7) Uani 1 1 d G . . . .
H71 H 0.667171 0.422707 0.966647 0.061 Uiso 1 1 calc R U . . .
C72 C 0.66059(4) 0.39925(4) 0.6913(4) 0.0813(11) Uani 1 1 d G . . . .
H72 H 0.672300 0.394558 0.736226 0.098 Uiso 1 1 calc R U . . .
C73 C 0.64651(4) 0.38940(4) 0.4888(3) 0.0842(11) Uani 1 1 d G . . . .
H73 H 0.648592 0.377972 0.395216 0.101 Uiso 1 1 calc R U . . .
C74 C 0.62938(3) 0.39627(3) 0.4231(3) 0.0595(8) Uani 1 1 d G . . . .
H74 H 0.619756 0.389536 0.284624 0.071 Uiso 1 1 calc R U . . .
C75 C 0.62633(3) 0.41299(3) 0.5599(3) 0.0404(6) Uani 1 1 d G . . . .
H75 H 0.614627 0.417685 0.515040 0.048 Uiso 1 1 calc R U . . .
C76 C 0.64042(3) 0.42284(3) 0.7625(2) 0.0343(5) Uani 1 1 d G . . . .
O77 O 0.63960(3) 0.44016(3) 0.9050(2) 0.0324(3) Uani 1 1 d . . . . .
C78 C 0.62154(4) 0.44707(4) 0.8541(3) 0.0271(5) Uani 1 1 d . . . . .
H78 H 0.622393 0.451538 0.683621 0.032 Uiso 1 1 calc R U . . .
C79 C 0.62774(4) 0.46929(4) 1.0060(4) 0.0305(5) Uani 1 1 d . . . . .
H79A H 0.616310 0.475281 0.970375 0.046 Uiso 1 1 calc R U . . .
H79B H 0.644688 0.482372 0.973468 0.046 Uiso 1 1 calc R U . . .
H79C H 0.626232 0.464617 1.172761 0.046 Uiso 1 1 calc R U . . .
C80 C 0.59566(4) 0.42604(4) 0.9140(3) 0.0253(4) Uani 1 1 d . . . . .
O81 O 0.59146(3) 0.41141(3) 1.0709(3) 0.0419(4) Uani 1 1 d . . . . .
O82 O 0.57867(2) 0.42686(3) 0.7832(2) 0.0275(3) Uani 1 1 d . . . . .
H82 H 0.565386 0.413354 0.793444 0.041 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 108.16(14) . . ?
C2 N1 H1A 110.1 . . ?
C5 N1 H1A 110.1 . . ?
C2 N1 H1B 110.1 . . ?
C5 N1 H1B 110.1 . . ?
H1A N1 H1B 108.4 . . ?
N1 C2 C3 103.48(15) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 103.49(16) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 104.86(15) . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C6 109.62(14) . . ?
N1 C5 C4 104.93(14) . . ?
C6 C5 C4 111.34(15) . . ?
N1 C5 H5 110.3 . . ?
C6 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?
O7 C6 O8 125.33(16) . . ?
O7 C6 C5 118.97(16) . . ?
O8 C6 C5 115.54(16) . . ?
C12 N11 C15 107.95(14) . . ?
C12 N11 H11A 110.1 . . ?
C15 N11 H11A 110.1 . . ?
C12 N11 H11B 110.1 . . ?
C15 N11 H11B 110.1 . . ?
H11A N11 H11B 108.4 . . ?
N11 C12 C13 103.14(16) . . ?
N11 C12 H12A 111.1 . . ?
C13 C12 H12A 111.1 . . ?
N11 C12 H12B 111.1 . . ?
C13 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C12 C13 C14 102.85(16) . . ?
C12 C13 H13A 111.2 . . ?
C14 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C13 C14 C15 104.65(16) . . ?
C13 C14 H14A 110.8 . . ?
C15 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C15 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
N11 C15 C16 109.04(14) . . ?
N11 C15 C14 104.92(15) . . ?
C16 C15 C14 111.91(15) . . ?
N11 C15 H15 110.3 . . ?
C16 C15 H15 110.3 . . ?
C14 C15 H15 110.3 . . ?
O17 C16 O18 124.91(16) . . ?
O17 C16 C15 118.62(16) . . ?
O18 C16 C15 116.33(16) . . ?
C22 N21 C25 108.56(14) . . ?
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 . . ?
N21 C22 C23 103.78(15) . . ?
N21 C22 H22A 111.0 . . ?
C23 C22 H22A 111.0 . . ?
N21 C22 H22B 111.0 . . ?
C23 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
C22 C23 C24 102.77(16) . . ?
C22 C23 H23A 111.2 . . ?
C24 C23 H23A 111.2 . . ?
C22 C23 H23B 111.2 . . ?
C24 C23 H23B 111.2 . . ?
H23A C23 H23B 109.1 . . ?
C23 C24 C25 104.44(16) . . ?
C23 C24 H24A 110.9 . . ?
C25 C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
C25 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
N21 C25 C26 109.87(15) . . ?
N21 C25 C24 104.44(14) . . ?
C26 C25 C24 111.34(15) . . ?
N21 C25 H25 110.4 . . ?
C26 C25 H25 110.4 . . ?
C24 C25 H25 110.4 . . ?
O27 C26 O28 125.43(16) . . ?
O27 C26 C25 118.22(16) . . ?
O28 C26 C25 116.18(16) . . ?
C32 C31 C36 119.58(18) . . ?
C32 C31 H31 120.2 . . ?
C36 C31 H31 120.2 . . ?
C31 C32 C33 120.47(19) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 119.39(19) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 121.19(18) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C36 118.98(18) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
O37 C36 C31 115.36(16) . . ?
O37 C36 C35 124.23(17) . . ?
C31 C36 C35 120.39(18) . . ?
C36 O37 C38 117.40(15) . . ?
O37 C38 C39 106.34(16) . . ?
O37 C38 C40 111.93(16) . . ?
C39 C38 C40 111.31(17) . . ?
O37 C38 H38 109.1 . . ?
C39 C38 H38 109.1 . . ?
C40 C38 H38 109.1 . . ?
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 124.41(19) . . ?
O41 C40 C38 120.95(19) . . ?
O42 C40 C38 114.63(17) . . ?
C40 O42 H42 109.5 . . ?
C52 C51 C56 119.79(18) . . ?
C52 C51 H51 120.1 . . ?
C56 C51 H51 120.1 . . ?
C51 C52 C53 120.68(19) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C54 C53 C52 119.00(19) . . ?
C54 C53 H53 120.5 . . ?
C52 C53 H53 120.5 . . ?
C53 C54 C55 121.20(19) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C56 C55 C54 119.07(19) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
O57 C56 C51 115.04(16) . . ?
O57 C56 C55 124.68(17) . . ?
C51 C56 C55 120.24(17) . . ?
C56 O57 C58 117.77(14) . . ?
O57 C58 C59 106.76(15) . . ?
O57 C58 C60 110.73(15) . . ?
C59 C58 C60 110.20(16) . . ?
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 124.73(18) . . ?
O61 C60 C58 123.58(17) . . ?
O62 C60 C58 111.64(16) . . ?
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 . . ?
C74 C73 C72 120.0 . . ?
C74 C73 H73 120.0 . . ?
C72 C73 H73 120.0 . . ?
C73 C74 C75 120.0 . . ?
C73 C74 H74 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 C76 120.0 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
O77 C76 C75 124.81(12) . . ?
O77 C76 C71 115.14(12) . . ?
C75 C76 C71 120.0 . . ?
C76 O77 C78 117.89(14) . . ?
O77 C78 C79 106.59(16) . . ?
O77 C78 C80 110.63(17) . . ?
C79 C78 C80 109.82(17) . . ?
O77 C78 H78 109.9 . . ?
C79 C78 H78 109.9 . . ?
C80 C78 H78 109.9 . . ?
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 124.75(19) . . ?
O81 C80 C78 123.49(19) . . ?
O82 C80 C78 111.65(17) . . ?
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 1.502(2) . ?
N1 C5 1.506(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C2 C3 1.505(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.542(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(2) . ?
C5 H5 1.0000 . ?
C6 O7 1.233(2) . ?
C6 O8 1.283(2) . ?
N11 C12 1.503(3) . ?
N11 C15 1.503(2) . ?
N11 H11A 0.9100 . ?
N11 H11B 0.9100 . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.523(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.541(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.528(2) . ?
C15 H15 1.0000 . ?
C16 O17 1.230(2) . ?
C16 O18 1.285(2) . ?
N21 C22 1.498(2) . ?
N21 C25 1.510(2) . ?
N21 H21A 0.9100 . ?
N21 H21B 0.9100 . ?
C22 C23 1.511(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.525(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.540(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.525(2) . ?
C25 H25 1.0000 . ?
C26 O27 1.237(2) . ?
C26 O28 1.283(2) . ?
C31 C32 1.383(3) . ?
C31 C36 1.390(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.395(3) . ?
C35 H35 0.9500 . ?
C36 O37 1.379(2) . ?
O37 C38 1.432(2) . ?
C38 C39 1.514(3) . ?
C38 C40 1.525(3) . ?
C38 H38 1.0000 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 O41 1.200(2) . ?
C40 O42 1.313(2) . ?
O42 H42 0.8400 . ?
C51 C52 1.384(3) . ?
C51 C56 1.390(3) . ?
C51 H51 0.9500 . ?
C52 C53 1.391(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.383(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.392(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.391(3) . ?
C55 H55 0.9500 . ?
C56 O57 1.383(2) . ?
O57 C58 1.424(2) . ?
C58 C59 1.522(3) . ?
C58 C60 1.527(3) . ?
C58 H58 1.0000 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 O61 1.203(2) . ?
C60 O62 1.319(2) . ?
O62 H62 0.8400 . ?
C71 C72 1.3900 . ?
C71 C76 1.3900 . ?
C71 H71 0.9500 . ?
C72 C73 1.3900 . ?
C72 H72 0.9500 . ?
C73 C74 1.3900 . ?
C73 H73 0.9500 . ?
C74 C75 1.3900 . ?
C74 H74 0.9500 . ?
C75 C76 1.3900 . ?
C75 H75 0.9500 . ?
C76 O77 1.3726(18) . ?
O77 C78 1.427(2) . ?
C78 C79 1.512(3) . ?
C78 C80 1.529(3) . ?
C78 H78 1.0000 . ?
C79 H79A 0.9800 . ?
C79 H79B 0.9800 . ?
C79 H79C 0.9800 . ?
C80 O81 1.207(2) . ?
C80 O82 1.318(2) . ?
O82 H82 0.8400 . ?
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 -28.64(18) . . . . ?
N1 C2 C3 C4 38.75(19) . . . . ?
C2 C3 C4 C5 -34.7(2) . . . . ?
C2 N1 C5 C6 -112.65(16) . . . . ?
C2 N1 C5 C4 7.02(19) . . . . ?
C3 C4 C5 N1 17.1(2) . . . . ?
C3 C4 C5 C6 135.57(17) . . . . ?
N1 C5 C6 O7 17.3(2) . . . . ?
C4 C5 C6 O7 -98.33(19) . . . . ?
N1 C5 C6 O8 -167.13(15) . . . . ?
C4 C5 C6 O8 77.2(2) . . . . ?
C15 N11 C12 C13 -29.59(19) . . . . ?
N11 C12 C13 C14 40.34(19) . . . . ?
C12 C13 C14 C15 -36.4(2) . . . . ?
C12 N11 C15 C16 -113.10(17) . . . . ?
C12 N11 C15 C14 6.93(19) . . . . ?
C13 C14 C15 N11 18.23(19) . . . . ?
C13 C14 C15 C16 136.33(17) . . . . ?
N11 C15 C16 O17 20.5(2) . . . . ?
C14 C15 C16 O17 -95.1(2) . . . . ?
N11 C15 C16 O18 -163.56(15) . . . . ?
C14 C15 C16 O18 80.8(2) . . . . ?
C25 N21 C22 C23 -25.13(19) . . . . ?
N21 C22 C23 C24 38.66(19) . . . . ?
C22 C23 C24 C25 -38.0(2) . . . . ?
C22 N21 C25 C26 -118.02(16) . . . . ?
C22 N21 C25 C24 1.48(19) . . . . ?
C23 C24 C25 N21 22.55(19) . . . . ?
C23 C24 C25 C26 141.07(16) . . . . ?
N21 C25 C26 O27 21.4(2) . . . . ?
C24 C25 C26 O27 -93.8(2) . . . . ?
N21 C25 C26 O28 -163.03(15) . . . . ?
C24 C25 C26 O28 81.8(2) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
C32 C31 C36 O37 -177.92(17) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
C34 C35 C36 O37 177.68(17) . . . . ?
C34 C35 C36 C31 -0.8(3) . . . . ?
C31 C36 O37 C38 -176.81(17) . . . . ?
C35 C36 O37 C38 4.7(3) . . . . ?
C36 O37 C38 C39 -172.67(16) . . . . ?
C36 O37 C38 C40 65.6(2) . . . . ?
O37 C38 C40 O41 -152.5(2) . . . . ?
C39 C38 C40 O41 88.7(3) . . . . ?
O37 C38 C40 O42 28.5(2) . . . . ?
C39 C38 C40 O42 -90.4(2) . . . . ?
C56 C51 C52 C53 0.2(3) . . . . ?
C51 C52 C53 C54 -1.2(3) . . . . ?
C52 C53 C54 C55 1.0(3) . . . . ?
C53 C54 C55 C56 0.3(3) . . . . ?
C52 C51 C56 O57 -176.56(17) . . . . ?
C52 C51 C56 C55 1.1(3) . . . . ?
C54 C55 C56 O57 176.11(17) . . . . ?
C54 C55 C56 C51 -1.3(3) . . . . ?
C51 C56 O57 C58 -177.20(16) . . . . ?
C55 C56 O57 C58 5.3(3) . . . . ?
C56 O57 C58 C59 -167.15(15) . . . . ?
C56 O57 C58 C60 72.88(19) . . . . ?
O57 C58 C60 O61 26.5(3) . . . . ?
C59 C58 C60 O61 -91.3(2) . . . . ?
O57 C58 C60 O62 -155.84(15) . . . . ?
C59 C58 C60 O62 86.27(19) . . . . ?
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 177.33(17) . . . . ?
C74 C75 C76 C71 0.0 . . . . ?
C72 C71 C76 O77 -177.58(16) . . . . ?
C72 C71 C76 C75 0.0 . . . . ?
C75 C76 O77 C78 5.7(2) . . . . ?
C71 C76 O77 C78 -176.89(14) . . . . ?
C76 O77 C78 C79 -169.85(15) . . . . ?
C76 O77 C78 C80 70.8(2) . . . . ?
O77 C78 C80 O81 31.2(3) . . . . ?
C79 C78 C80 O81 -86.2(3) . . . . ?
O77 C78 C80 O82 -152.57(16) . . . . ?
C79 C78 C80 O82 90.0(2) . . . . ?
