#------------------------------------------------------------------------------
#$Date: 2022-01-16 17:33:20 +0200 (Sun, 16 Jan 2022) $
#$Revision: 272077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/92/4519273.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_4519273
loop_
_publ_author_name
'Li, Puzhen'
'Zhang, Meng'
'Maris, Thierry'
'Zhu, X. X.'
'Wuest, James D.'
_publ_section_title
;
 Probing the Relationship between Gelation and Crystallization by Using
 Salts of Lithocholic Acid
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              643
_journal_page_last               652
_journal_paper_doi               10.1021/acs.cgd.1c01182
_journal_volume                  22
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H39 O3, C3 H10 N, H2 O'
_chemical_formula_sum            'C27 H51 N O4'
_chemical_formula_weight         453.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2021-02-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.277(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2848(2)
_cell_length_b                   7.0415(1)
_cell_length_c                   15.9198(3)
_cell_measurement_reflns_used    9373
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.594
_cell_measurement_theta_min      3.317
_cell_volume                     1299.91(4)
_computing_cell_refinement
;
SAINT (2013) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40683
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.597
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.85
_diffrn_source_power             0.199215
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.5163
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1033 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.8499.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       Plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0506P)²+0.1319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5789
_reflns_number_total             5857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            LCA_iPrNH3_H2O_zhu18.cif
_cod_data_source_block           zhu18
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               4519273
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C17(H17), C20(H20), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B),
 C23(H23A,H23B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.45036(8) 0.62248(16) 0.90967(6) 0.0286(2) Uani 1 1 d . . . . .
H1 H 0.4298(18) 0.714(4) 0.9348(15) 0.043 Uiso 1 1 d . U . . .
O2 O 0.22095(9) 0.73125(15) 0.06608(7) 0.0286(2) Uani 1 1 d . . . . .
O3 O 0.14024(8) 0.44508(16) 0.03706(7) 0.0295(2) Uani 1 1 d . . . . .
C1 C 0.27676(11) 0.27623(18) 0.73827(8) 0.0218(3) Uani 1 1 d . . . . .
H1A H 0.222530 0.233136 0.768539 0.026 Uiso 1 1 calc R U . . .
H1B H 0.301517 0.162693 0.712633 0.026 Uiso 1 1 calc R U . . .
C2 C 0.38264(11) 0.3629(2) 0.80790(8) 0.0236(3) Uani 1 1 d . . . . .
H2A H 0.416601 0.269522 0.855932 0.028 Uiso 1 1 calc R U . . .
H2B H 0.441438 0.394272 0.779983 0.028 Uiso 1 1 calc R U . . .
C3 C 0.34913(11) 0.5415(2) 0.84698(8) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.293506 0.507248 0.878359 0.027 Uiso 1 1 calc R U . . .
C4 C 0.29208(11) 0.68242(19) 0.77304(8) 0.0216(2) Uani 1 1 d . . . . .
H4A H 0.348480 0.721839 0.744106 0.026 Uiso 1 1 calc R U . . .
H4B H 0.269162 0.796944 0.799180 0.026 Uiso 1 1 calc R U . . .
C5 C 0.18530(10) 0.59837(19) 0.70255(8) 0.0204(2) Uani 1 1 d . . . . .
H5 H 0.128591 0.566848 0.733329 0.024 Uiso 1 1 calc R U . . .
C6 C 0.12849(11) 0.7481(2) 0.63150(8) 0.0232(3) Uani 1 1 d . . . . .
H6A H 0.050810 0.703420 0.595120 0.028 Uiso 1 1 calc R U . . .
H6B H 0.119115 0.867608 0.661126 0.028 Uiso 1 1 calc R U . . .
C7 C 0.19958(11) 0.78727(19) 0.57070(8) 0.0222(3) Uani 1 1 d . . . . .
H7A H 0.274683 0.843374 0.605916 0.027 Uiso 1 1 calc R U . . .
H7B H 0.158440 0.879890 0.524293 0.027 Uiso 1 1 calc R U . . .
C8 C 0.21987(10) 0.60395(18) 0.52663(8) 0.0188(2) Uani 1 1 d . . . . .
H8 H 0.142897 0.551072 0.491051 0.023 Uiso 1 1 calc R U . . .
C9 C 0.28189(10) 0.45504(18) 0.59784(8) 0.0177(2) Uani 1 1 d . . . . .
H9 H 0.355763 0.514777 0.635414 0.021 Uiso 1 1 calc R U . . .
C10 C 0.21159(10) 0.41056(18) 0.66139(8) 0.0191(2) Uani 1 1 d . . . . .
C11 C 0.31534(12) 0.27529(18) 0.55641(9) 0.0222(2) Uani 1 1 d . . . . .
H11A H 0.368769 0.198353 0.604586 0.027 Uiso 1 1 calc R U . . .
H11B H 0.245022 0.198548 0.528945 0.027 Uiso 1 1 calc R U . . .
C12 C 0.37291(11) 0.31504(19) 0.48544(8) 0.0207(2) Uani 1 1 d . . . . .
H12A H 0.450448 0.369910 0.514581 0.025 Uiso 1 1 calc R U . . .
H12B H 0.382567 0.193948 0.457099 0.025 Uiso 1 1 calc R U . . .
C13 C 0.30119(10) 0.45241(17) 0.41377(8) 0.0173(2) Uani 1 1 d . . . . .
C14 C 0.28868(10) 0.63500(18) 0.46377(8) 0.0182(2) Uani 1 1 d . . . . .
H14 H 0.368211 0.673399 0.501386 0.022 Uiso 1 1 calc R U . . .
C15 C 0.24632(12) 0.78445(19) 0.39084(9) 0.0240(3) Uani 1 1 d . . . . .
H15A H 0.265156 0.914126 0.415366 0.029 Uiso 1 1 calc R U . . .
H15B H 0.161981 0.774622 0.360754 0.029 Uiso 1 1 calc R U . . .
C16 C 0.31249(12) 0.73622(19) 0.32630(9) 0.0237(3) Uani 1 1 d . . . . .
H16A H 0.376547 0.827161 0.334136 0.028 Uiso 1 1 calc R U . . .
H16B H 0.260171 0.743861 0.263951 0.028 Uiso 1 1 calc R U . . .
C17 C 0.36055(10) 0.53091(18) 0.34788(8) 0.0182(2) Uani 1 1 d . . . . .
H17 H 0.445000 0.541264 0.381269 0.022 Uiso 1 1 calc R U . . .
C18 C 0.18281(10) 0.3668(2) 0.36170(8) 0.0219(2) Uani 1 1 d . . . . .
H18A H 0.193604 0.253526 0.329539 0.033 Uiso 1 1 calc R U . . .
H18B H 0.136966 0.460575 0.319145 0.033 Uiso 1 1 calc R U . . .
H18C H 0.142486 0.331697 0.403253 0.033 Uiso 1 1 calc R U . . .
C19 C 0.09657(11) 0.3122(2) 0.61022(9) 0.0248(3) Uani 1 1 d . . . . .
H19A H 0.112098 0.185231 0.591659 0.037 Uiso 1 1 calc R U . . .
H19B H 0.055335 0.387579 0.557570 0.037 Uiso 1 1 calc R U . . .
H19C H 0.049220 0.301359 0.648915 0.037 Uiso 1 1 calc R U . . .
C20 C 0.34660(11) 0.41658(18) 0.26250(8) 0.0198(2) Uani 1 1 d . . . . .
H20 H 0.262190 0.407199 0.228841 0.024 Uiso 1 1 calc R U . . .
C21 C 0.39346(15) 0.2147(2) 0.28142(10) 0.0331(3) Uani 1 1 d . . . . .
H21A H 0.473907 0.218884 0.320687 0.050 Uiso 1 1 calc R U . . .
H21B H 0.389234 0.152541 0.225359 0.050 Uiso 1 1 calc R U . . .
H21C H 0.347334 0.143082 0.310373 0.050 Uiso 1 1 calc R U . . .
C22 C 0.40400(10) 0.51611(19) 0.20151(8) 0.0214(2) Uani 1 1 d . . . . .
H22A H 0.399576 0.655360 0.208351 0.026 Uiso 1 1 calc R U . . .
H22B H 0.486514 0.480327 0.220440 0.026 Uiso 1 1 calc R U . . .
C23 C 0.34656(11) 0.4634(2) 0.10282(8) 0.0228(3) Uani 1 1 d . . . . .
H23A H 0.395311 0.508259 0.068203 0.027 Uiso 1 1 calc R U . . .
H23B H 0.339838 0.323602 0.096829 0.027 Uiso 1 1 calc R U . . .
C24 C 0.22703(11) 0.5527(2) 0.06555(8) 0.0216(2) Uani 1 1 d . . . . .
N1 N -0.08666(10) 0.55549(19) 0.00996(7) 0.0238(2) Uani 1 1 d . . . . .
H1C H -0.1128(17) 0.670(3) -0.0157(14) 0.036 Uiso 1 1 d . U . . .
H1D H -0.1276(17) 0.457(3) -0.0216(14) 0.036 Uiso 1 1 d . U . . .
H1E H -0.0150(19) 0.539(3) 0.0121(14) 0.036 Uiso 1 1 d . U . . .
C25 C -0.09157(12) 0.5525(2) 0.10308(9) 0.0287(3) Uani 1 1 d . . . . .
H25 H -0.173138 0.573663 0.100417 0.034 Uiso 1 1 calc R U . . .
C26 C -0.05292(14) 0.3583(3) 0.14324(10) 0.0371(4) Uani 1 1 d . . . . .
H26A H -0.102864 0.260426 0.106189 0.056 Uiso 1 1 calc R U . . .
H26B H -0.057906 0.353128 0.203384 0.056 Uiso 1 1 calc R U . . .
H26C H 0.026959 0.335962 0.146096 0.056 Uiso 1 1 calc R U . . .
C27 C -0.01773(13) 0.7131(3) 0.15528(10) 0.0343(3) Uani 1 1 d . . . . .
H27A H 0.061503 0.698139 0.155104 0.051 Uiso 1 1 calc R U . . .
H27B H -0.018158 0.710431 0.216716 0.051 Uiso 1 1 calc R U . . .
H27C H -0.048771 0.834778 0.127782 0.051 Uiso 1 1 calc R U . . .
O4 O 0.63157(9) 0.40899(17) 1.01139(7) 0.0311(2) Uani 1 1 d . . . . .
H4C H 0.671(2) 0.358(4) 0.9755(15) 0.047 Uiso 1 1 d . U . . .
H4D H 0.576(2) 0.475(4) 0.9763(15) 0.047 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C3 O1 H1 108.0(15) . .
H1A C1 H1B 107.5 . .
C2 C1 H1A 108.5 . .
C2 C1 H1B 108.5 . .
C2 C1 C10 115.09(11) . .
C10 C1 H1A 108.5 . .
C10 C1 H1B 108.5 . .
C1 C2 H2A 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
C3 C2 C1 110.26(10) . .
C3 C2 H2A 109.6 . .
C3 C2 H2B 109.6 . .
O1 C3 C2 108.96(10) . .
O1 C3 H3 109.1 . .
O1 C3 C4 110.59(11) . .
C2 C3 H3 109.1 . .
C2 C3 C4 109.94(10) . .
C4 C3 H3 109.1 . .
C3 C4 H4A 109.2 . .
C3 C4 H4B 109.2 . .
C3 C4 C5 112.21(11) . .
H4A C4 H4B 107.9 . .
C5 C4 H4A 109.2 . .
C5 C4 H4B 109.2 . .
C4 C5 H5 107.0 . .
C4 C5 C6 110.16(11) . .
C4 C5 C10 112.91(10) . .
C6 C5 H5 107.0 . .
C6 C5 C10 112.35(10) . .
C10 C5 H5 107.0 . .
C5 C6 H6A 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C7 C6 C5 112.03(10) . .
C7 C6 H6A 109.2 . .
C7 C6 H6B 109.2 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
C6 C7 C8 110.63(11) . .
H7A C7 H7B 108.1 . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C7 C8 H8 107.9 . .
C7 C8 C9 110.57(9) . .
C9 C8 H8 107.9 . .
C14 C8 C7 112.97(10) . .
C14 C8 H8 107.9 . .
C14 C8 C9 109.43(9) . .
C8 C9 H9 106.5 . .
C8 C9 C10 111.49(9) . .
C10 C9 H9 106.5 . .
C11 C9 C8 112.24(9) . .
C11 C9 H9 106.5 . .
C11 C9 C10 113.20(10) . .
C1 C10 C5 108.18(10) . .
C1 C10 C9 112.51(10) . .
C5 C10 C9 109.75(10) . .
C19 C10 C1 106.76(10) . .
C19 C10 C5 108.82(10) . .
C19 C10 C9 110.70(9) . .
C9 C11 H11A 108.6 . .
C9 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C12 C11 C9 114.51(10) . .
C12 C11 H11A 108.6 . .
C12 C11 H11B 108.6 . .
C11 C12 H12A 109.3 . .
C11 C12 H12B 109.3 . .
H12A C12 H12B 107.9 . .
C13 C12 C11 111.69(10) . .
C13 C12 H12A 109.3 . .
C13 C12 H12B 109.3 . .
C12 C13 C14 105.78(9) . .
C12 C13 C17 116.22(10) . .
C12 C13 C18 111.24(10) . .
C14 C13 C17 101.49(9) . .
C18 C13 C14 111.48(10) . .
C18 C13 C17 110.13(9) . .
C8 C14 C13 112.93(10) . .
C8 C14 H14 106.8 . .
C8 C14 C15 118.36(10) . .
C13 C14 H14 106.8 . .
C15 C14 C13 104.40(9) . .
C15 C14 H14 106.8 . .
C14 C15 H15A 111.1 . .
C14 C15 H15B 111.1 . .
C14 C15 C16 103.44(10) . .
H15A C15 H15B 109.0 . .
C16 C15 H15A 111.1 . .
C16 C15 H15B 111.1 . .
C15 C16 H16A 110.2 . .
C15 C16 H16B 110.2 . .
C15 C16 C17 107.59(10) . .
H16A C16 H16B 108.5 . .
C17 C16 H16A 110.2 . .
C17 C16 H16B 110.2 . .
C13 C17 H17 107.5 . .
C16 C17 C13 104.45(10) . .
C16 C17 H17 107.5 . .
C20 C17 C13 117.83(10) . .
C20 C17 C16 111.55(9) . .
C20 C17 H17 107.5 . .
C13 C18 H18A 109.5 . .
C13 C18 H18B 109.5 . .
C13 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C10 C19 H19A 109.5 . .
C10 C19 H19B 109.5 . .
C10 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C20 H20 107.5 . .
C17 C20 C22 112.15(10) . .
C21 C20 C17 112.83(11) . .
C21 C20 H20 107.5 . .
C21 C20 C22 109.04(10) . .
C22 C20 H20 107.5 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.1 . .
C20 C22 H22B 109.1 . .
H22A C22 H22B 107.8 . .
C23 C22 C20 112.44(10) . .
C23 C22 H22A 109.1 . .
C23 C22 H22B 109.1 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 108.1 . .
C24 C23 C22 110.82(10) . .
C24 C23 H23A 109.5 . .
C24 C23 H23B 109.5 . .
O2 C24 O3 123.78(13) . .
O2 C24 C23 117.41(12) . .
O3 C24 C23 118.80(12) . .
H1C N1 H1D 112.3(17) . .
H1C N1 H1E 109.6(19) . .
H1D N1 H1E 106.7(19) . .
C25 N1 H1C 109.3(13) . .
C25 N1 H1D 109.9(13) . .
C25 N1 H1E 109.0(14) . .
N1 C25 H25 108.8 . .
N1 C25 C26 108.62(13) . .
N1 C25 C27 108.58(12) . .
C26 C25 H25 108.8 . .
C27 C25 H25 108.8 . .
C27 C25 C26 113.22(12) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
H4C O4 H4D 106(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.84(3) .
O1 C3 1.4313(15) .
O2 C24 1.2595(18) .
O3 C24 1.2641(17) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.5301(18) .
C1 C10 1.5449(17) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.5190(18) .
C3 H3 1.0000 .
C3 C4 1.5221(17) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.5357(17) .
C5 H5 1.0000 .
C5 C6 1.5350(17) .
C5 C10 1.5564(17) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.5276(18) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.5285(17) .
C8 H8 1.0000 .
C8 C9 1.5475(16) .
C8 C14 1.5239(16) .
C9 H9 1.0000 .
C9 C10 1.5635(16) .
C9 C11 1.5443(17) .
C10 C19 1.5426(17) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.5435(17) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.5329(16) .
C13 C14 1.5462(17) .
C13 C17 1.5630(16) .
C13 C18 1.5395(16) .
C14 H14 1.0000 .
C14 C15 1.5255(16) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.5437(18) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.5565(18) .
C17 H17 1.0000 .
C17 C20 1.5398(17) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20 1.0000 .
C20 C21 1.5258(18) .
C20 C22 1.5437(16) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C22 C23 1.5401(17) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C23 C24 1.5259(17) .
N1 H1C 0.91(2) .
N1 H1D 0.91(2) .
N1 H1E 0.88(2) .
N1 C25 1.5036(16) .
C25 H25 1.0000 .
C25 C26 1.518(2) .
C25 C27 1.515(2) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
O4 H4C 0.93(2) .
O4 H4D 0.86(3) .
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
O1 H1 O4 0.84(3) 1.90(3) 2.7382(16) 174(2) 2_657 yes
N1 H1C O3 0.91(2) 1.98(2) 2.8625(17) 163.2(19) 2 yes
N1 H1D O2 0.91(2) 1.95(2) 2.8427(16) 167.9(19) 2_545 yes
N1 H1E O3 0.88(2) 1.93(2) 2.7868(16) 164(2) . yes
O4 H4C O2 0.93(2) 1.90(3) 2.8009(16) 164(2) 2_646 yes
O4 H4D O1 0.86(3) 1.87(3) 2.7308(15) 175(2) . 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
O1 C3 C4 C5 178.03(10) . . . .
C1 C2 C3 O1 -178.16(10) . . . .
C1 C2 C3 C4 -56.82(14) . . . .
C2 C1 C10 C5 -51.87(14) . . . .
C2 C1 C10 C9 69.54(13) . . . .
C2 C1 C10 C19 -168.84(10) . . . .
C2 C3 C4 C5 57.66(14) . . . .
C3 C4 C5 C6 177.92(10) . . . .
C3 C4 C5 C10 -55.58(14) . . . .
C4 C5 C6 C7 72.27(13) . . . .
C4 C5 C10 C1 50.34(13) . . . .
C4 C5 C10 C9 -72.76(12) . . . .
C4 C5 C10 C19 165.96(10) . . . .
C5 C6 C7 C8 56.63(14) . . . .
C6 C5 C10 C1 175.66(10) . . . .
C6 C5 C10 C9 52.57(13) . . . .
C6 C5 C10 C19 -68.71(13) . . . .
C6 C7 C8 C9 -58.01(13) . . . .
C6 C7 C8 C14 178.97(10) . . . .
C7 C8 C9 C10 57.72(13) . . . .
C7 C8 C9 C11 -174.08(10) . . . .
C7 C8 C14 C13 -175.61(9) . . . .
C7 C8 C14 C15 -53.24(14) . . . .
C8 C9 C10 C1 -174.77(10) . . . .
C8 C9 C10 C5 -54.26(12) . . . .
C8 C9 C10 C19 65.88(13) . . . .
C8 C9 C11 C12 46.24(14) . . . .
C8 C14 C15 C16 -164.10(10) . . . .
C9 C8 C14 C13 60.74(12) . . . .
C9 C8 C14 C15 -176.89(10) . . . .
C9 C11 C12 C13 -51.94(14) . . . .
C10 C1 C2 C3 56.49(14) . . . .
C10 C5 C6 C7 -54.54(14) . . . .
C10 C9 C11 C12 173.53(10) . . . .
C11 C9 C10 C1 57.54(13) . . . .
C11 C9 C10 C5 178.05(10) . . . .
C11 C9 C10 C19 -61.81(13) . . . .
C11 C12 C13 C14 58.00(13) . . . .
C11 C12 C13 C17 169.70(10) . . . .
C11 C12 C13 C18 -63.21(13) . . . .
C12 C13 C14 C8 -64.74(12) . . . .
C12 C13 C14 C15 165.38(10) . . . .
C12 C13 C17 C16 -146.33(10) . . . .
C12 C13 C17 C20 89.27(13) . . . .
C13 C14 C15 C16 -37.54(12) . . . .
C13 C17 C20 C21 -59.48(14) . . . .
C13 C17 C20 C22 176.92(10) . . . .
C14 C8 C9 C10 -177.23(9) . . . .
C14 C8 C9 C11 -49.03(13) . . . .
C14 C13 C17 C16 -32.17(11) . . . .
C14 C13 C17 C20 -156.56(10) . . . .
C14 C15 C16 C17 16.67(13) . . . .
C15 C16 C17 C13 9.96(12) . . . .
C15 C16 C17 C20 138.29(11) . . . .
C16 C17 C20 C21 179.74(11) . . . .
C16 C17 C20 C22 56.13(13) . . . .
C17 C13 C14 C8 173.53(9) . . . .
C17 C13 C14 C15 43.65(11) . . . .
C17 C20 C22 C23 -152.96(10) . . . .
C18 C13 C14 C8 56.30(13) . . . .
C18 C13 C14 C15 -73.57(12) . . . .
C18 C13 C17 C16 86.03(12) . . . .
C18 C13 C17 C20 -38.37(14) . . . .
C20 C22 C23 C24 70.76(14) . . . .
C21 C20 C22 C23 81.34(13) . . . .
C22 C23 C24 O2 60.97(15) . . . .
C22 C23 C24 O3 -118.23(13) . . . .

_cod_database_fobs_code 4519273
