#------------------------------------------------------------------------------
#$Date: 2022-04-01 01:37:38 +0300 (Fri, 01 Apr 2022) $
#$Revision: 274181 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244701.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_7244701
loop_
_publ_author_name
'Chahine, Ali'
'Chaffee, Alan L.'
'Knowles, Gregory P.'
'Turner, David Roger'
'Batten, Stuart R.'
_publ_section_title
;
 Highly Connected Framework Materials from Flexible Tetra-Isophthalate
 Ligands
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00269H
_journal_year                    2022
_chemical_formula_moiety         'Cl, C39 H35 N2 O16, 3(H2 O)'
_chemical_formula_sum            'C39 H41 Cl N2 O19'
_chemical_formula_weight         877.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-04-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-02-10 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                83.42(3)
_cell_angle_beta                 80.88(3)
_cell_angle_gamma                78.36(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4300(19)
_cell_length_b                   9.790(2)
_cell_length_c                   21.430(4)
_cell_measurement_reflns_used    47129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      0.966
_cell_volume                     1906.2(7)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47129
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.733
_diffrn_reflns_theta_min         0.966
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       plate
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   0.4376
_exptl_transmission_factor_min   0.3176
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         7993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0628
_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)+(0.1417P)²+0.7186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6860
_reflns_number_total             7993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00269h2.cif
_cod_data_source_block           L2
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '__diffrn_radiation_type' was replaced with
'_diffrn_radiation_type'.

Automatic conversion script
Id: cif_correct_tags 7550 2019-12-06 10:49:48Z antanas 

The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7244701
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H8 of O8, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups, H14 of O14, H12 of O12, H10 of O10, H15 of O15, H5 of O5,
   H2 of O2, H3 of O3
2.a Free rotating group:
 O17(H17A,H17B), O18(H18A,H18B), O19(H19C,H19D)
2.b Ternary CH refined with riding coordinates:
 N1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C31(H31A,H31B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C8(H8A), C12(H12A), C15(H15A), C18(H18), C24(H24), C27(H27),
 C30(H30), C33(H33), C36(H36), C39(H39)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5), O8(H8), O10(H10), O12(H12), O14(H14), O15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl1 Cl 0.34857(6) 0.22867(5) 0.10137(2) 0.02516(18) Uani 1 1 d . . . . .
O1 O 1.19958(19) 0.11156(19) -0.01857(8) 0.0302(4) Uani 1 1 d . . . . .
O2 O 1.18372(19) -0.04836(17) 0.06537(8) 0.0298(4) Uani 1 1 d . . . . .
H2 H 1.267098 -0.081571 0.049924 0.045 Uiso 1 1 calc R U . . .
O3 O 0.8066(2) 0.52939(19) -0.01807(9) 0.0368(5) Uani 1 1 d . . . . .
H3 H 0.759533 0.599050 -0.035408 0.055 Uiso 1 1 calc R U . . .
O4 O 0.6068(2) 0.54999(19) 0.05555(10) 0.0415(5) Uani 1 1 d . . . . .
O5 O 1.08160(19) -0.33106(17) 0.14588(9) 0.0303(4) Uani 1 1 d . . . . .
H5 H 1.169994 -0.360676 0.139897 0.045 Uiso 1 1 calc R U . . .
O6 O 1.07914(18) -0.54921(17) 0.19068(8) 0.0277(4) Uani 1 1 d . . . . .
O7 O 0.61563(19) -0.64892(17) 0.31341(8) 0.0286(4) Uani 1 1 d . . . . .
O8 O 0.41013(18) -0.48919(17) 0.31208(8) 0.0276(4) Uani 1 1 d . . . . .
H8 H 0.372321 -0.554775 0.329342 0.033 Uiso 1 1 calc R U . . .
O9 O 0.19300(19) 0.84538(18) 0.25083(9) 0.0323(4) Uani 1 1 d . . . . .
O10 O -0.02910(18) 0.98124(17) 0.26826(8) 0.0286(4) Uani 1 1 d . . . . .
H10 H 0.013204 1.041567 0.248425 0.043 Uiso 1 1 calc R U . . .
O11 O -0.45017(17) 0.80778(16) 0.38054(8) 0.0255(4) Uani 1 1 d . . . . .
O12 O -0.42492(17) 0.59368(17) 0.43219(8) 0.0271(4) Uani 1 1 d . . . . .
H12 H -0.514113 0.615302 0.440221 0.041 Uiso 1 1 calc R U . . .
O13 O -0.27727(17) 0.33380(16) 0.53975(8) 0.0234(3) Uani 1 1 d . . . . .
O14 O -0.26433(17) 0.13134(16) 0.60108(8) 0.0261(4) Uani 1 1 d . . . . .
H14 H -0.353701 0.151855 0.603981 0.039 Uiso 1 1 calc R U . . .
O15 O 0.20776(18) -0.18128(17) 0.61810(8) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.266524 -0.240924 0.635524 0.039 Uiso 1 1 calc R U . . .
O16 O 0.40920(18) -0.13842(17) 0.55413(8) 0.0285(4) Uani 1 1 d . . . . .
N1 N 0.54572(19) 0.04829(17) 0.19139(8) 0.0185(4) Uani 1 1 d . . . . .
H1 H 0.496351 0.129832 0.166924 0.022 Uiso 1 1 calc R U . . .
N2 N 0.24939(19) 0.32474(17) 0.36393(8) 0.0174(4) Uani 1 1 d . . . . .
C1 C 1.1338(3) 0.0674(2) 0.03037(10) 0.0240(5) Uani 1 1 d . . . . .
C2 C 0.9850(2) 0.1382(2) 0.05870(10) 0.0217(4) Uani 1 1 d . . . . .
C3 C 0.9249(3) 0.2697(2) 0.03189(10) 0.0244(5) Uani 1 1 d . . . . .
H3A H 0.974619 0.310121 -0.004248 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7896(3) 0.3406(2) 0.05957(11) 0.0248(5) Uani 1 1 d . . . . .
C5 C 0.7245(3) 0.4829(3) 0.03247(12) 0.0299(5) Uani 1 1 d . . . . .
C6 C 0.7135(2) 0.2783(2) 0.11317(11) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.624439 0.326525 0.131812 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7700(2) 0.1440(2) 0.13899(10) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.9077(2) 0.0760(2) 0.11138(10) 0.0213(4) Uani 1 1 d . . . . .
H8A H 0.947857 -0.012209 0.128643 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6930(2) 0.0802(2) 0.19841(10) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.679006 0.143610 0.231412 0.025 Uiso 1 1 calc R U . . .
H9B H 0.755240 -0.005972 0.212152 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5544(2) -0.0778(2) 0.15370(10) 0.0196(4) Uani 1 1 d . . . . .
H10A H 0.456003 -0.085945 0.148884 0.024 Uiso 1 1 calc R U . . .
H10B H 0.606384 -0.060281 0.111622 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6297(2) -0.2159(2) 0.18362(10) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.5531(2) -0.3031(2) 0.22594(10) 0.0197(4) Uani 1 1 d . . . . .
H12A H 0.453364 -0.274837 0.238331 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6256(2) -0.4337(2) 0.25008(10) 0.0196(4) Uani 1 1 d . . . . .
C14 C 0.5451(2) -0.5322(2) 0.29576(10) 0.0217(4) Uani 1 1 d . . . . .
C15 C 0.7752(2) -0.4755(2) 0.23138(10) 0.0202(4) Uani 1 1 d . . . . .
H15A H 0.823419 -0.562269 0.246782 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8528(2) -0.3879(2) 0.18979(10) 0.0201(4) Uani 1 1 d . . . . .
C17 C 1.0149(2) -0.4312(2) 0.17468(10) 0.0226(5) Uani 1 1 d . . . . .
C18 C 0.7804(2) -0.2592(2) 0.16475(10) 0.0206(4) Uani 1 1 d . . . . .
H18 H 0.831770 -0.202352 0.135708 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4521(2) 0.0388(2) 0.25535(10) 0.0199(4) Uani 1 1 d . . . . .
H19A H 0.511541 -0.010851 0.286854 0.024 Uiso 1 1 calc R U . . .
H19B H 0.375520 -0.012665 0.253220 0.024 Uiso 1 1 calc R U . . .
C20 C 0.3840(2) 0.1865(2) 0.27449(9) 0.0192(4) Uani 1 1 d . . . . .
H20A H 0.456142 0.246495 0.263739 0.023 Uiso 1 1 calc R U . . .
H20B H 0.302756 0.225122 0.251195 0.023 Uiso 1 1 calc R U . . .
C21 C 0.3304(2) 0.1828(2) 0.34537(9) 0.0185(4) Uani 1 1 d . . . . .
H21A H 0.266245 0.115297 0.356743 0.022 Uiso 1 1 calc R U . . .
H21B H 0.413307 0.153035 0.368571 0.022 Uiso 1 1 calc R U . . .
C22 C 0.0978(2) 0.3518(2) 0.34593(10) 0.0193(4) Uani 1 1 d . . . . .
H22A H 0.041147 0.291519 0.374058 0.023 Uiso 1 1 calc R U . . .
H22B H 0.104701 0.324698 0.303253 0.023 Uiso 1 1 calc R U . . .
C23 C 0.0149(2) 0.5008(2) 0.34811(10) 0.0202(4) Uani 1 1 d . . . . .
C24 C 0.0774(2) 0.6104(2) 0.31438(10) 0.0203(4) Uani 1 1 d . . . . .
H24 H 0.174490 0.593226 0.295674 0.024 Uiso 1 1 calc R U . . .
C25 C -0.0061(2) 0.7458(2) 0.30872(10) 0.0200(4) Uani 1 1 d . . . . .
C26 C 0.0649(2) 0.8608(2) 0.27281(10) 0.0225(5) Uani 1 1 d . . . . .
C27 C -0.1531(2) 0.7706(2) 0.33558(10) 0.0200(4) Uani 1 1 d . . . . .
H27 H -0.209686 0.859658 0.330618 0.024 Uiso 1 1 calc R U . . .
C28 C -0.2148(2) 0.6626(2) 0.36965(10) 0.0194(4) Uani 1 1 d . . . . .
C29 C -0.3743(2) 0.6940(2) 0.39515(10) 0.0201(4) Uani 1 1 d . . . . .
C30 C -0.1307(2) 0.5272(2) 0.37684(10) 0.0196(4) Uani 1 1 d . . . . .
H30 H -0.171752 0.455610 0.400564 0.024 Uiso 1 1 calc R U . . .
C31 C 0.2515(2) 0.3423(2) 0.43303(9) 0.0182(4) Uani 1 1 d . . . . .
H31A H 0.352288 0.329784 0.440442 0.022 Uiso 1 1 calc R U . . .
H31B H 0.204470 0.437146 0.441679 0.022 Uiso 1 1 calc R U . . .
C32 C 0.1762(2) 0.2414(2) 0.47902(9) 0.0178(4) Uani 1 1 d . . . . .
C33 C 0.0262(2) 0.2754(2) 0.50054(9) 0.0187(4) Uani 1 1 d . . . . .
H33 H -0.027189 0.360655 0.486193 0.022 Uiso 1 1 calc R U . . .
C34 C -0.0443(2) 0.1839(2) 0.54298(9) 0.0177(4) Uani 1 1 d . . . . .
C35 C -0.2065(2) 0.2236(2) 0.56168(10) 0.0186(4) Uani 1 1 d . . . . .
C36 C 0.0352(2) 0.0567(2) 0.56671(10) 0.0179(4) Uani 1 1 d . . . . .
H36 H -0.011348 -0.004413 0.595427 0.022 Uiso 1 1 calc R U . . .
C37 C 0.1853(2) 0.0234(2) 0.54649(9) 0.0186(4) Uani 1 1 d . . . . .
C38 C 0.2790(2) -0.1070(2) 0.57289(10) 0.0195(4) Uani 1 1 d . . . . .
C39 C 0.2547(2) 0.1141(2) 0.50266(9) 0.0181(4) Uani 1 1 d . . . . .
H39 H 0.354352 0.089698 0.488980 0.022 Uiso 1 1 calc R U . . .
O17 O 1.3550(2) -0.4623(2) 0.14362(10) 0.0371(4) Uani 1 1 d G . . . .
H17A H 1.334723 -0.540269 0.137813 0.056 Uiso 1 1 d G U . . .
H17B H 1.427565 -0.445959 0.116782 0.056 Uiso 1 1 d G U . . .
O18 O 1.4555(2) -0.1659(2) 0.02950(9) 0.0353(4) Uani 1 1 d G . . . .
H18A H 1.483752 -0.249974 0.043816 0.053 Uiso 1 1 d G U . . .
H18B H 1.499467 -0.152133 -0.007801 0.053 Uiso 1 1 d G U . . .
O19 O 0.0889(2) 1.17518(18) 0.20406(9) 0.0332(4) Uani 1 1 d G . . . .
H19C H 0.154279 1.159560 0.172183 0.050 Uiso 1 1 d G U . . .
H19D H 0.057417 1.262961 0.199995 0.050 Uiso 1 1 d G 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 109.5 . . ?
C5 O3 H3 109.5 . . ?
C17 O5 H5 109.5 . . ?
C14 O8 H8 109.5 . . ?
C26 O10 H10 109.5 . . ?
C29 O12 H12 109.5 . . ?
C35 O14 H14 109.5 . . ?
C38 O15 H15 109.5 . . ?
C9 N1 H1 106.1 . . ?
C9 N1 C10 114.38(16) . . ?
C10 N1 H1 106.1 . . ?
C19 N1 H1 106.1 . . ?
C19 N1 C9 110.46(16) . . ?
C19 N1 C10 112.89(17) . . ?
C21 N2 C31 112.05(15) . . ?
C22 N2 C21 109.92(16) . . ?
C22 N2 C31 113.34(15) . . ?
O1 C1 O2 124.6(2) . . ?
O1 C1 C2 123.5(2) . . ?
O2 C1 C2 111.9(2) . . ?
C3 C2 C1 118.9(2) . . ?
C8 C2 C1 121.2(2) . . ?
C8 C2 C3 119.9(2) . . ?
C2 C3 H3A 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C6 120.0(2) . . ?
C6 C4 C5 119.3(2) . . ?
O3 C5 C4 113.2(2) . . ?
O4 C5 O3 123.6(2) . . ?
O4 C5 C4 123.1(2) . . ?
C4 C6 H6 119.6 . . ?
C7 C6 C4 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 C9 120.87(19) . . ?
C8 C7 C9 120.53(19) . . ?
C2 C8 C7 121.2(2) . . ?
C2 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
N1 C9 H9A 108.7 . . ?
N1 C9 H9B 108.7 . . ?
C7 C9 N1 114.28(17) . . ?
C7 C9 H9A 108.7 . . ?
C7 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 N1 114.45(16) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 122.16(19) . . ?
C12 C11 C18 119.69(19) . . ?
C18 C11 C10 118.1(2) . . ?
C11 C12 H12A 119.8 . . ?
C11 C12 C13 120.44(19) . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 121.82(19) . . ?
C15 C13 C12 119.5(2) . . ?
C15 C13 C14 118.66(18) . . ?
O7 C14 O8 125.3(2) . . ?
O7 C14 C13 118.3(2) . . ?
O8 C14 C13 116.47(19) . . ?
C13 C15 H15A 119.8 . . ?
C16 C15 C13 120.31(19) . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C17 118.81(18) . . ?
C15 C16 C18 120.2(2) . . ?
C18 C16 C17 120.9(2) . . ?
O5 C17 C16 114.21(18) . . ?
O6 C17 O5 123.7(2) . . ?
O6 C17 C16 122.1(2) . . ?
C11 C18 H18 120.1 . . ?
C16 C18 C11 119.8(2) . . ?
C16 C18 H18 120.1 . . ?
N1 C19 H19A 109.8 . . ?
N1 C19 H19B 109.8 . . ?
N1 C19 C20 109.55(17) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C19 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.48(17) . . ?
C21 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
N2 C21 C20 111.18(16) . . ?
N2 C21 H21A 109.4 . . ?
N2 C21 H21B 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N2 C22 H22A 108.3 . . ?
N2 C22 H22B 108.3 . . ?
N2 C22 C23 116.03(18) . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
C24 C23 C22 119.86(19) . . ?
C30 C23 C22 119.9(2) . . ?
C30 C23 C24 119.75(18) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 118.7(2) . . ?
C27 C25 C24 119.7(2) . . ?
C27 C25 C26 121.54(18) . . ?
O9 C26 O10 124.2(2) . . ?
O9 C26 C25 123.78(19) . . ?
O10 C26 C25 112.06(19) . . ?
C25 C27 H27 119.9 . . ?
C28 C27 C25 120.15(18) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C29 117.75(17) . . ?
C27 C28 C30 120.4(2) . . ?
C30 C28 C29 121.8(2) . . ?
O11 C29 O12 123.7(2) . . ?
O11 C29 C28 120.4(2) . . ?
O12 C29 C28 115.83(17) . . ?
C23 C30 C28 119.7(2) . . ?
C23 C30 H30 120.2 . . ?
C28 C30 H30 120.2 . . ?
N2 C31 H31A 108.7 . . ?
N2 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C32 C31 N2 114.13(17) . . ?
C32 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C33 C32 C31 120.53(18) . . ?
C39 C32 C31 121.17(19) . . ?
C39 C32 C33 118.3(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.13(18) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C35 118.42(18) . . ?
C33 C34 C36 120.29(19) . . ?
C36 C34 C35 121.3(2) . . ?
O13 C35 O14 124.0(2) . . ?
O13 C35 C34 121.5(2) . . ?
O14 C35 C34 114.53(17) . . ?
C34 C36 H36 120.6 . . ?
C37 C36 C34 118.9(2) . . ?
C37 C36 H36 120.6 . . ?
C36 C37 C38 121.8(2) . . ?
C39 C37 C36 120.52(18) . . ?
C39 C37 C38 117.65(19) . . ?
O15 C38 C37 114.10(18) . . ?
O16 C38 O15 123.89(19) . . ?
O16 C38 C37 122.0(2) . . ?
C32 C39 H39 119.6 . . ?
C37 C39 C32 120.87(19) . . ?
C37 C39 H39 119.6 . . ?
H17A O17 H17B 109.5 . . ?
H18A O18 H18B 109.5 . . ?
H19C O19 H19D 104.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.331(3) . ?
O3 H3 0.8200 . ?
O3 C5 1.321(3) . ?
O4 C5 1.230(3) . ?
O5 H5 0.8200 . ?
O5 C17 1.313(3) . ?
O6 C17 1.229(3) . ?
O7 C14 1.251(3) . ?
O8 H8 0.8200 . ?
O8 C14 1.263(3) . ?
O9 C26 1.211(3) . ?
O10 H10 0.8200 . ?
O10 C26 1.328(3) . ?
O11 C29 1.233(3) . ?
O12 H12 0.8200 . ?
O12 C29 1.309(3) . ?
O13 C35 1.234(3) . ?
O14 H14 0.8200 . ?
O14 C35 1.306(3) . ?
O15 H15 0.8200 . ?
O15 C38 1.322(3) . ?
O16 C38 1.218(3) . ?
N1 H1 0.9800 . ?
N1 C9 1.517(3) . ?
N1 C10 1.533(2) . ?
N1 C19 1.512(3) . ?
N2 C21 1.508(2) . ?
N2 C22 1.503(3) . ?
N2 C31 1.514(2) . ?
C1 C2 1.500(3) . ?
C2 C3 1.396(3) . ?
C2 C8 1.392(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.399(3) . ?
C4 C5 1.495(3) . ?
C4 C6 1.401(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(3) . ?
C7 C8 1.406(3) . ?
C7 C9 1.499(3) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(3) . ?
C11 C12 1.391(3) . ?
C11 C18 1.406(3) . ?
C12 H12A 0.9300 . ?
C12 C13 1.406(3) . ?
C13 C14 1.519(3) . ?
C13 C15 1.394(3) . ?
C15 H15A 0.9300 . ?
C15 C16 1.392(3) . ?
C16 C17 1.495(3) . ?
C16 C18 1.398(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.522(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.511(3) . ?
C23 C24 1.401(3) . ?
C23 C30 1.399(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.402(3) . ?
C25 C26 1.500(3) . ?
C25 C27 1.398(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(3) . ?
C28 C29 1.498(3) . ?
C28 C30 1.406(3) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.513(3) . ?
C32 C33 1.401(3) . ?
C32 C39 1.400(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.390(3) . ?
C34 C35 1.501(3) . ?
C34 C36 1.404(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.396(3) . ?
C37 C38 1.506(3) . ?
C37 C39 1.395(3) . ?
C39 H39 0.9300 . ?
O17 H17A 0.8506 . ?
O17 H17B 0.8499 . ?
O18 H18A 0.8498 . ?
O18 H18B 0.8495 . ?
O19 H19C 0.8502 . ?
O19 H19D 0.8498 . ?
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
_geom_hbond_publ_flag
O2 H2 O18 0.82 1.81 2.621(2) 170.3 . yes
O5 H5 O17 0.82 1.83 2.634(3) 164.6 . yes
O8 H8 N2 0.82 1.83 2.640(3) 167.0 1_545 yes
O10 H10 O19 0.82 1.73 2.550(3) 175.1 . yes
O12 H12 O13 0.82 1.92 2.740(2) 179.2 2_466 yes
O14 H14 O11 0.82 1.80 2.613(2) 173.8 2_466 yes
O15 H15 O7 0.82 1.80 2.606(2) 168.8 2_646 yes
O17 H17B O4 0.85 1.97 2.803(3) 168.3 1_645 yes
O18 H18A O4 0.85 2.08 2.895(3) 161.7 1_645 yes
O19 H19D O6 0.85 1.88 2.665(3) 153.9 1_475 yes
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
O1 C1 C2 C3 -7.6(3) . . . . ?
O1 C1 C2 C8 173.3(2) . . . . ?
O2 C1 C2 C3 172.4(2) . . . . ?
O2 C1 C2 C8 -6.8(3) . . . . ?
N1 C10 C11 C12 90.4(2) . . . . ?
N1 C10 C11 C18 -93.1(2) . . . . ?
N1 C19 C20 C21 -162.17(18) . . . . ?
N2 C22 C23 C24 54.3(3) . . . . ?
N2 C22 C23 C30 -134.0(2) . . . . ?
N2 C31 C32 C33 -88.6(2) . . . . ?
N2 C31 C32 C39 93.4(2) . . . . ?
C1 C2 C3 C4 -176.7(2) . . . . ?
C1 C2 C8 C7 178.3(2) . . . . ?
C2 C3 C4 C5 178.8(2) . . . . ?
C2 C3 C4 C6 -1.4(4) . . . . ?
C3 C2 C8 C7 -0.9(3) . . . . ?
C3 C4 C5 O3 0.1(3) . . . . ?
C3 C4 C5 O4 -179.1(3) . . . . ?
C3 C4 C6 C7 -1.1(4) . . . . ?
C4 C6 C7 C8 2.6(3) . . . . ?
C4 C6 C7 C9 176.6(2) . . . . ?
C5 C4 C6 C7 178.7(2) . . . . ?
C6 C4 C5 O3 -179.7(2) . . . . ?
C6 C4 C5 O4 1.1(4) . . . . ?
C6 C7 C8 C2 -1.6(3) . . . . ?
C6 C7 C9 N1 66.7(3) . . . . ?
C8 C2 C3 C4 2.4(3) . . . . ?
C8 C7 C9 N1 -119.5(2) . . . . ?
C9 N1 C10 C11 62.7(2) . . . . ?
C9 N1 C19 C20 79.5(2) . . . . ?
C9 C7 C8 C2 -175.6(2) . . . . ?
C10 N1 C9 C7 73.3(2) . . . . ?
C10 N1 C19 C20 -150.99(17) . . . . ?
C10 C11 C12 C13 176.65(18) . . . . ?
C10 C11 C18 C16 -178.06(18) . . . . ?
C11 C12 C13 C14 -179.29(18) . . . . ?
C11 C12 C13 C15 0.1(3) . . . . ?
C12 C11 C18 C16 -1.5(3) . . . . ?
C12 C13 C14 O7 177.33(19) . . . . ?
C12 C13 C14 O8 -1.6(3) . . . . ?
C12 C13 C15 C16 0.9(3) . . . . ?
C13 C15 C16 C17 175.36(18) . . . . ?
C13 C15 C16 C18 -2.1(3) . . . . ?
C14 C13 C15 C16 -179.76(18) . . . . ?
C15 C13 C14 O7 -2.0(3) . . . . ?
C15 C13 C14 O8 179.03(19) . . . . ?
C15 C16 C17 O5 -166.85(19) . . . . ?
C15 C16 C17 O6 10.1(3) . . . . ?
C15 C16 C18 C11 2.5(3) . . . . ?
C17 C16 C18 C11 -174.98(18) . . . . ?
C18 C11 C12 C13 0.3(3) . . . . ?
C18 C16 C17 O5 10.6(3) . . . . ?
C18 C16 C17 O6 -172.4(2) . . . . ?
C19 N1 C9 C7 -158.06(16) . . . . ?
C19 N1 C10 C11 -64.8(2) . . . . ?
C19 C20 C21 N2 -174.19(17) . . . . ?
C21 N2 C22 C23 -167.03(17) . . . . ?
C21 N2 C31 C32 -62.7(2) . . . . ?
C22 N2 C21 C20 77.4(2) . . . . ?
C22 N2 C31 C32 62.4(2) . . . . ?
C22 C23 C24 C25 170.97(18) . . . . ?
C22 C23 C30 C28 -169.41(18) . . . . ?
C23 C24 C25 C26 179.39(18) . . . . ?
C23 C24 C25 C27 -1.6(3) . . . . ?
C24 C23 C30 C28 2.3(3) . . . . ?
C24 C25 C26 O9 -3.8(3) . . . . ?
C24 C25 C26 O10 176.43(19) . . . . ?
C24 C25 C27 C28 2.3(3) . . . . ?
C25 C27 C28 C29 -177.65(17) . . . . ?
C25 C27 C28 C30 -0.7(3) . . . . ?
C26 C25 C27 C28 -178.69(18) . . . . ?
C27 C25 C26 O9 177.1(2) . . . . ?
C27 C25 C26 O10 -2.6(3) . . . . ?
C27 C28 C29 O11 7.4(3) . . . . ?
C27 C28 C29 O12 -173.48(18) . . . . ?
C27 C28 C30 C23 -1.6(3) . . . . ?
C29 C28 C30 C23 175.22(18) . . . . ?
C30 C23 C24 C25 -0.7(3) . . . . ?
C30 C28 C29 O11 -169.53(19) . . . . ?
C30 C28 C29 O12 9.6(3) . . . . ?
C31 N2 C21 C20 -155.62(18) . . . . ?
C31 N2 C22 C23 66.7(2) . . . . ?
C31 C32 C33 C34 -179.77(17) . . . . ?
C31 C32 C39 C37 178.11(18) . . . . ?
C32 C33 C34 C35 -177.05(17) . . . . ?
C32 C33 C34 C36 2.0(3) . . . . ?
C33 C32 C39 C37 0.1(3) . . . . ?
C33 C34 C35 O13 0.8(3) . . . . ?
C33 C34 C35 O14 179.25(17) . . . . ?
C33 C34 C36 C37 -0.6(3) . . . . ?
C34 C36 C37 C38 176.25(17) . . . . ?
C34 C36 C37 C39 -1.0(3) . . . . ?
C35 C34 C36 C37 178.40(17) . . . . ?
C36 C34 C35 O13 -178.25(18) . . . . ?
C36 C34 C35 O14 0.2(3) . . . . ?
C36 C37 C38 O15 -2.9(3) . . . . ?
C36 C37 C38 O16 177.9(2) . . . . ?
C36 C37 C39 C32 1.3(3) . . . . ?
C38 C37 C39 C32 -176.07(17) . . . . ?
C39 C32 C33 C34 -1.7(3) . . . . ?
C39 C37 C38 O15 174.38(18) . . . . ?
C39 C37 C38 O16 -4.8(3) . . . . ?
