#------------------------------------------------------------------------------
#$Date: 2022-05-05 19:28:51 +0300 (Thu, 05 May 2022) $
#$Revision: 274929 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/94/4519429.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_4519429
loop_
_publ_author_name
'Li, Puzhen'
'Zhang, Meng'
'Maris, Thierry'
'Zhu, X. X.'
'Wuest, James D.'
_publ_contact_author_id_orcid    0000-0001-9731-4046
_publ_section_title
;
 Probing the Relationship between Crystallization and Gelation by Using
 Ammonium Salts of Bile Acids
;
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3505
_journal_page_last               3517
_journal_paper_doi               10.1021/acs.cgd.2c00310
_journal_volume                  22
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H39 O5, 2(H2 O), C8 H20 N'
_chemical_formula_sum            'C32 H63 N O7'
_chemical_formula_weight         573.83
_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_email      thierry.maris@umontreal.ca
_audit_contact_author_name       'Thierry Maris'
_audit_contact_author_phone      '+1 514 340 4711 2579'
_audit_creation_date             2021-10-28
_audit_creation_method
;
FinalCif V90 by Daniel Kratzert, Freiburg 2021,
https://dkratzert.de/finalcif.html
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.6675(3)
_cell_length_b                   7.5914(2)
_cell_length_c                   16.1130(3)
_cell_measurement_reflns_used    5555
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.71
_cell_measurement_theta_min      2.77
_cell_volume                     1657.08(6)
_computing_cell_refinement
;
SAINT (2020) 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 (2020) 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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21635
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.103
_diffrn_reflns_theta_min         2.767
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.0291265
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8545.
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    1.150
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5724
_refine_ls_number_restraints     448
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0802
_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)+(0.1197P)²+1.3633P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2235
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                5590
_reflns_number_total             5724
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            CA_OctylNH3_2H2O.cif
_cod_data_source_block           zhu33
_cod_database_code               4519429
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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 -0.1569(3) 0.3251(15) 0.2380(3) 0.145(4) Uani 1 1 d . U . . .
H1 H -0.121764 0.287645 0.292101 0.217 Uiso 1 1 d R U . . .
O2 O 0.1262(3) 0.7391(8) 0.2653(2) 0.0741(15) Uani 1 1 d . U . . .
H2 H 0.169258 0.772768 0.304142 0.111 Uiso 1 1 calc R U . . .
O3 O 0.2888(2) 0.2413(6) 0.36830(17) 0.0413(7) Uani 1 1 d . U . . .
H3 H 0.268774 0.139986 0.378644 0.062 Uiso 1 1 calc R U . . .
O4 O 0.7733(2) 0.4102(6) 0.5974(2) 0.0476(8) Uani 1 1 d . U . . .
O5 O 0.8744(3) 0.2614(6) 0.5278(2) 0.0527(9) Uani 1 1 d . U . . .
C1 C 0.0480(5) 0.1804(13) 0.1161(4) 0.0783(12) Uani 1 1 d . U . . .
H1A H 0.007779 0.171860 0.060392 0.094 Uiso 1 1 calc R U . . .
H1B H 0.093327 0.078112 0.121967 0.094 Uiso 1 1 calc R U . . .
C2 C -0.0198(5) 0.1677(14) 0.1823(4) 0.0833(13) Uani 1 1 d . U . . .
H2A H -0.057138 0.055686 0.175306 0.100 Uiso 1 1 calc R U . . .
H2B H 0.019996 0.166438 0.238273 0.100 Uiso 1 1 calc R U . . .
C3 C -0.0914(5) 0.3196(14) 0.1773(4) 0.0841(13) Uani 1 1 d . U . . .
H3A H -0.133044 0.311044 0.121564 0.101 Uiso 1 1 calc R U . . .
C4 C -0.0361(5) 0.4957(13) 0.1783(4) 0.0787(12) Uani 1 1 d . U . . .
H4A H -0.084171 0.592919 0.166279 0.094 Uiso 1 1 calc R U . . .
H4B H 0.001000 0.515676 0.234531 0.094 Uiso 1 1 calc R U . . .
C5 C 0.0341(5) 0.4954(12) 0.1140(4) 0.0730(10) Uani 1 1 d . U . . .
H5 H -0.007073 0.486160 0.058090 0.088 Uiso 1 1 calc R U . . .
C6 C 0.0854(5) 0.6676(12) 0.1158(3) 0.0684(11) Uani 1 1 d . U . . .
H6A H 0.035120 0.761160 0.116716 0.082 Uiso 1 1 calc R U . . .
H6B H 0.113559 0.680074 0.062543 0.082 Uiso 1 1 calc R U . . .
C7 C 0.1720(4) 0.7048(11) 0.1911(3) 0.0619(10) Uani 1 1 d . U . . .
H7 H 0.208862 0.812528 0.177474 0.074 Uiso 1 1 calc R U . . .
C8 C 0.2422(4) 0.5519(10) 0.2003(3) 0.0534(8) Uani 1 1 d . U . . .
H8 H 0.277932 0.552489 0.150039 0.064 Uiso 1 1 calc R U . . .
C9 C 0.1850(4) 0.3731(10) 0.1991(3) 0.0553(8) Uani 1 1 d . U . . .
H9 H 0.144998 0.379917 0.246698 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1087(4) 0.3465(12) 0.1187(3) 0.0690(10) Uani 1 1 d . U . . .
C11 C 0.2507(4) 0.2168(9) 0.2170(3) 0.0503(9) Uani 1 1 d . U . . .
H11A H 0.282552 0.190963 0.166667 0.060 Uiso 1 1 calc R U . . .
H11B H 0.209407 0.113909 0.227197 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3307(3) 0.2379(8) 0.2914(2) 0.0412(8) Uani 1 1 d . U . . .
H12 H 0.376041 0.134348 0.292744 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3911(3) 0.4045(7) 0.2836(3) 0.0385(7) Uani 1 1 d . U . . .
C14 C 0.3199(3) 0.5627(8) 0.2765(3) 0.0394(7) Uani 1 1 d . U . . .
H14 H 0.284213 0.559282 0.326836 0.047 Uiso 1 1 calc R U . . .
C15 C 0.3869(3) 0.7203(7) 0.2864(3) 0.0422(8) Uani 1 1 d . U . . .
H15A H 0.353581 0.821660 0.309364 0.051 Uiso 1 1 calc R U . . .
H15B H 0.407166 0.754720 0.231925 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4777(3) 0.6599(7) 0.3486(3) 0.0426(8) Uani 1 1 d . U . . .
H16A H 0.479670 0.723166 0.402493 0.051 Uiso 1 1 calc R U . . .
H16B H 0.539655 0.684204 0.325089 0.051 Uiso 1 1 calc R U . . .
C17 C 0.4652(3) 0.4572(7) 0.3617(3) 0.0393(8) Uani 1 1 d . U . . .
H17 H 0.431126 0.440862 0.412402 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4482(4) 0.3899(7) 0.2074(3) 0.0410(10) Uani 1 1 d . U . . .
H18A H 0.486773 0.497515 0.202867 0.061 Uiso 1 1 calc R U . . .
H18B H 0.492715 0.288298 0.214644 0.061 Uiso 1 1 calc R U . . .
H18C H 0.401379 0.374749 0.156332 0.061 Uiso 1 1 calc R U . . .
C19 C 0.1635(5) 0.3491(14) 0.0394(3) 0.085(2) Uani 1 1 d . U . . .
H19A H 0.203557 0.456240 0.039735 0.127 Uiso 1 1 calc R U . . .
H19B H 0.206277 0.245488 0.039831 0.127 Uiso 1 1 calc R U . . .
H19C H 0.114862 0.347345 -0.011116 0.127 Uiso 1 1 calc R U . . .
C20 C 0.5632(3) 0.3545(8) 0.3762(3) 0.0480(9) Uani 1 1 d . U . . .
H20 H 0.597713 0.371075 0.325760 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5486(5) 0.1573(9) 0.3879(4) 0.0678(19) Uani 1 1 d . U . . .
H21A H 0.505546 0.110271 0.339448 0.102 Uiso 1 1 calc R U . . .
H21B H 0.612655 0.097601 0.392950 0.102 Uiso 1 1 calc R U . . .
H21C H 0.518050 0.137197 0.438797 0.102 Uiso 1 1 calc R U . . .
C22 C 0.6299(4) 0.4255(10) 0.4516(3) 0.0555(10) Uani 1 1 d . U . . .
H22A H 0.603300 0.393127 0.503755 0.067 Uiso 1 1 calc R U . . .
H22B H 0.633489 0.555504 0.448520 0.067 Uiso 1 1 calc R U . . .
C23 C 0.7347(3) 0.3439(10) 0.4514(3) 0.0554(10) Uani 1 1 d . U . . .
H23A H 0.727207 0.219114 0.433962 0.067 Uiso 1 1 calc R U . . .
H23B H 0.768132 0.406259 0.409068 0.067 Uiso 1 1 calc R U . . .
C24 C 0.7978(3) 0.3519(8) 0.5316(3) 0.0427(9) Uani 1 1 d . U . . .
O6 O 0.1339(3) 0.3961(7) 0.4348(2) 0.0573(10) Uani 1 1 d G . . . .
H6C H 0.193306 0.379227 0.426498 0.086 Uiso 1 1 d G U . . .
H6D H 0.117645 0.492490 0.409916 0.086 Uiso 1 1 d G U . . .
O7 O -0.0415(3) 0.2264(10) 0.3881(3) 0.095(2) Uani 1 1 d G . . . .
H7A H -0.073144 0.258951 0.427494 0.142 Uiso 1 1 d G U . . .
H7B H 0.015963 0.202147 0.412389 0.142 Uiso 1 1 d G U . . .
N1A N 1.0268(7) 0.3270(14) 0.6416(8) 0.051(2) Uani 0.543(5) 1 d D U P A -1
H1AA H 0.975592 0.262425 0.615644 0.061 Uiso 0.543(5) 1 calc R U P A -1
H1AB H 1.022824 0.331668 0.697531 0.061 Uiso 0.543(5) 1 calc R U P A -1
H1AC H 1.023908 0.438156 0.620273 0.061 Uiso 0.543(5) 1 calc R U P A -1
C1A C 1.1219(6) 0.2433(18) 0.6277(9) 0.0789(18) Uani 0.543(5) 1 d D U P A -1
H1AD H 1.123554 0.235575 0.566554 0.095 Uiso 0.543(5) 1 calc R U P A -1
H1AE H 1.122390 0.121294 0.649466 0.095 Uiso 0.543(5) 1 calc R U P A -1
C2A C 1.2147(7) 0.3330(19) 0.6664(6) 0.0814(15) Uani 0.543(5) 1 d D U P A -1
H2AA H 1.269754 0.289048 0.637917 0.098 Uiso 0.543(5) 1 calc R U P A -1
H2AB H 1.207731 0.460464 0.654145 0.098 Uiso 0.543(5) 1 calc R U P A -1
C3A C 1.2440(8) 0.312(2) 0.7590(6) 0.0838(16) Uani 0.543(5) 1 d D U P A -1
H3AA H 1.189973 0.362034 0.787013 0.101 Uiso 0.543(5) 1 calc R U P A -1
H3AB H 1.246339 0.184443 0.771146 0.101 Uiso 0.543(5) 1 calc R U P A -1
C4A C 1.3388(8) 0.391(2) 0.8008(10) 0.0886(15) Uani 0.543(5) 1 d D U P A -1
H4AA H 1.365530 0.436722 0.750950 0.106 Uiso 0.543(5) 1 calc R U P A -1
H4AB H 1.312327 0.496151 0.826210 0.106 Uiso 0.543(5) 1 calc R U P A -1
C5A C 1.4332(8) 0.368(2) 0.8588(8) 0.0919(16) Uani 0.543(5) 1 d D U P A -1
H5AA H 1.421729 0.249862 0.881565 0.110 Uiso 0.543(5) 1 calc R U P A -1
H5AB H 1.479107 0.346148 0.817269 0.110 Uiso 0.543(5) 1 calc R U P A -1
C6A C 1.5044(8) 0.440(2) 0.9294(8) 0.0930(17) Uani 0.543(5) 1 d D U P A -1
H6AA H 1.462777 0.457697 0.974542 0.112 Uiso 0.543(5) 1 calc R U P A -1
H6AB H 1.518246 0.560264 0.909959 0.112 Uiso 0.543(5) 1 calc R U P A -1
C7A C 1.6017(8) 0.3835(19) 0.9759(10) 0.0932(19) Uani 0.543(5) 1 d D U P A -1
H7AA H 1.589278 0.292715 1.017416 0.112 Uiso 0.543(5) 1 calc R U P A -1
H7AB H 1.641030 0.327810 0.935722 0.112 Uiso 0.543(5) 1 calc R U P A -1
C8A C 1.6616(11) 0.529(2) 1.0207(12) 0.113(5) Uani 0.543(5) 1 d D U P A -1
H8AA H 1.723584 0.480065 1.049196 0.169 Uiso 0.543(5) 1 calc R U P A -1
H8AB H 1.676201 0.617736 0.980072 0.169 Uiso 0.543(5) 1 calc R U P A -1
H8AC H 1.624344 0.582570 1.061932 0.169 Uiso 0.543(5) 1 calc R U P A -1
N1B N 1.0207(8) 0.4104(18) 0.6519(9) 0.051(2) Uani 0.457(5) 1 d D U P A -2
H1BA H 0.979667 0.361021 0.609084 0.061 Uiso 0.457(5) 1 calc R U P A -2
H1BB H 0.995500 0.393989 0.700791 0.061 Uiso 0.457(5) 1 calc R U P A -2
H1BC H 1.026511 0.527835 0.642234 0.061 Uiso 0.457(5) 1 calc R U P A -2
C1B C 1.1198(7) 0.326(2) 0.6575(9) 0.0795(17) Uani 0.457(5) 1 d D U P A -2
H1BD H 1.147882 0.342598 0.604499 0.095 Uiso 0.457(5) 1 calc R U P A -2
H1BE H 1.114358 0.197908 0.667800 0.095 Uiso 0.457(5) 1 calc R U P A -2
C2B C 1.1852(7) 0.4106(18) 0.7285(9) 0.0819(16) Uani 0.457(5) 1 d D U P A -2
H2BA H 1.152050 0.404273 0.779513 0.098 Uiso 0.457(5) 1 calc R U P A -2
H2BB H 1.193115 0.536713 0.715210 0.098 Uiso 0.457(5) 1 calc R U P A -2
C3B C 1.2856(7) 0.3287(18) 0.7471(7) 0.0850(15) Uani 0.457(5) 1 d D U P A -2
H3BA H 1.278557 0.210979 0.772158 0.102 Uiso 0.457(5) 1 calc R U P A -2
H3BB H 1.312816 0.311522 0.693778 0.102 Uiso 0.457(5) 1 calc R U P A -2
C4B C 1.3577(8) 0.4346(17) 0.8052(9) 0.0893(16) Uani 0.457(5) 1 d D U P A -2
H4BA H 1.419107 0.448587 0.779527 0.107 Uiso 0.457(5) 1 calc R U P A -2
H4BB H 1.329749 0.553495 0.811288 0.107 Uiso 0.457(5) 1 calc R U P A -2
C5B C 1.3831(6) 0.355(2) 0.8906(6) 0.0911(16) Uani 0.457(5) 1 d D U P A -2
H5BA H 1.344391 0.245913 0.893632 0.109 Uiso 0.457(5) 1 calc R U P A -2
H5BB H 1.363047 0.438439 0.932645 0.109 Uiso 0.457(5) 1 calc R U P A -2
C6B C 1.4906(8) 0.313(2) 0.9133(8) 0.0934(17) Uani 0.457(5) 1 d D U P A -2
H6BA H 1.498730 0.183505 0.914367 0.112 Uiso 0.457(5) 1 calc R U P A -2
H6BB H 1.527262 0.359811 0.868992 0.112 Uiso 0.457(5) 1 calc R U P A -2
C7B C 1.5357(9) 0.386(3) 0.9960(8) 0.0939(18) Uani 0.457(5) 1 d D U P A -2
H7BA H 1.498643 0.340448 1.040195 0.113 Uiso 0.457(5) 1 calc R U P A -2
H7BB H 1.528067 0.516003 0.994710 0.113 Uiso 0.457(5) 1 calc R U P A -2
C8B C 1.6429(9) 0.343(4) 1.0191(12) 0.117(6) Uani 0.457(5) 1 d D U P A -2
H8BA H 1.666833 0.395095 1.073666 0.176 Uiso 0.457(5) 1 calc R U P A -2
H8BB H 1.651190 0.214784 1.022161 0.176 Uiso 0.457(5) 1 calc R U P A -2
H8BC H 1.680661 0.390614 0.976606 0.176 Uiso 0.457(5) 1 calc R U P A -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O1 H1 109.0 . .
C7 O2 H2 109.5 . .
C12 O3 H3 109.5 . .
H1A C1 H1B 107.5 . .
C2 C1 H1A 108.5 . .
C2 C1 H1B 108.5 . .
C2 C1 C10 114.9(6) . .
C10 C1 H1A 108.5 . .
C10 C1 H1B 108.5 . .
C1 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
C3 C2 C1 111.7(7) . .
C3 C2 H2A 109.3 . .
C3 C2 H2B 109.3 . .
O1 C3 C2 116.9(8) . .
O1 C3 H3A 106.6 . .
O1 C3 C4 108.9(7) . .
C2 C3 H3A 106.6 . .
C2 C3 C4 110.5(6) . .
C4 C3 H3A 106.6 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C5 C4 C3 110.5(7) . .
C5 C4 H4A 109.5 . .
C5 C4 H4B 109.5 . .
C4 C5 H5 106.7 . .
C4 C5 C10 117.0(6) . .
C6 C5 C4 109.3(6) . .
C6 C5 H5 106.7 . .
C6 C5 C10 110.0(6) . .
C10 C5 H5 106.7 . .
C5 C6 H6A 107.8 . .
C5 C6 H6B 107.8 . .
C5 C6 C7 118.0(5) . .
H6A C6 H6B 107.1 . .
C7 C6 H6A 107.8 . .
C7 C6 H6B 107.8 . .
O2 C7 C6 107.5(4) . .
O2 C7 H7 108.7 . .
O2 C7 C8 113.5(4) . .
C6 C7 H7 108.7 . .
C8 C7 C6 109.7(6) . .
C8 C7 H7 108.7 . .
C7 C8 H8 106.9 . .
C7 C8 C9 111.0(5) . .
C7 C8 C14 114.1(5) . .
C9 C8 H8 106.9 . .
C14 C8 H8 106.9 . .
C14 C8 C9 110.6(4) . .
C8 C9 H9 105.6 . .
C8 C9 C10 113.5(5) . .
C10 C9 H9 105.6 . .
C11 C9 C8 113.6(4) . .
C11 C9 H9 105.6 . .
C11 C9 C10 112.0(5) . .
C1 C10 C5 104.9(5) . .
C1 C10 C9 115.8(6) . .
C1 C10 C19 108.0(6) . .
C5 C10 C9 108.3(5) . .
C5 C10 C19 109.9(6) . .
C19 C10 C9 109.7(5) . .
C9 C11 H11A 108.6 . .
C9 C11 H11B 108.6 . .
C9 C11 C12 114.8(5) . .
H11A C11 H11B 107.5 . .
C12 C11 H11A 108.6 . .
C12 C11 H11B 108.6 . .
O3 C12 C11 110.8(4) . .
O3 C12 H12 108.3 . .
O3 C12 C13 109.9(4) . .
C11 C12 H12 108.3 . .
C11 C12 C13 111.3(4) . .
C13 C12 H12 108.3 . .
C12 C13 C14 108.0(4) . .
C12 C13 C17 116.6(3) . .
C12 C13 C18 110.0(4) . .
C14 C13 C17 101.3(4) . .
C14 C13 C18 112.2(4) . .
C18 C13 C17 108.5(3) . .
C8 C14 C13 112.7(4) . .
C8 C14 H14 106.9 . .
C13 C14 H14 106.9 . .
C15 C14 C8 118.7(4) . .
C15 C14 C13 104.1(4) . .
C15 C14 H14 106.9 . .
C14 C15 H15A 110.8 . .
C14 C15 H15B 110.8 . .
C14 C15 C16 104.8(4) . .
H15A C15 H15B 108.9 . .
C16 C15 H15A 110.8 . .
C16 C15 H15B 110.8 . .
C15 C16 H16A 110.4 . .
C15 C16 H16B 110.4 . .
C15 C16 C17 106.6(4) . .
H16A C16 H16B 108.6 . .
C17 C16 H16A 110.4 . .
C17 C16 H16B 110.4 . .
C13 C17 C16 102.3(4) . .
C13 C17 H17 107.7 . .
C16 C17 H17 107.7 . .
C20 C17 C13 116.8(4) . .
C20 C17 C16 114.2(4) . .
C20 C17 H17 107.7 . .
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 107.9 . .
C21 C20 C17 113.0(5) . .
C21 C20 H20 107.9 . .
C22 C20 C17 111.0(4) . .
C22 C20 H20 107.9 . .
C22 C20 C21 108.9(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 110.1 . .
C20 C22 H22B 110.1 . .
C20 C22 C23 108.2(4) . .
H22A C22 H22B 108.4 . .
C23 C22 H22A 110.1 . .
C23 C22 H22B 110.1 . .
C22 C23 H23A 108.6 . .
C22 C23 H23B 108.6 . .
H23A C23 H23B 107.6 . .
C24 C23 C22 114.7(4) . .
C24 C23 H23A 108.6 . .
C24 C23 H23B 108.6 . .
O4 C24 O5 124.0(5) . .
O4 C24 C23 125.4(4) . .
O5 C24 C23 109.4(4) . .
H6C O6 H6D 104.5 . .
H7A O7 H7B 104.5 . .
H1AA N1A H1AB 109.5 . .
H1AA N1A H1AC 109.5 . .
H1AB N1A H1AC 109.5 . .
C1A N1A H1AA 109.5 . .
C1A N1A H1AB 109.5 . .
C1A N1A H1AC 109.5 . .
N1A C1A H1AD 108.1 . .
N1A C1A H1AE 108.1 . .
N1A C1A C2A 116.7(11) . .
H1AD C1A H1AE 107.3 . .
C2A C1A H1AD 108.1 . .
C2A C1A H1AE 108.1 . .
C1A C2A H2AA 107.9 . .
C1A C2A H2AB 107.9 . .
H2AA C2A H2AB 107.2 . .
C3A C2A C1A 117.8(10) . .
C3A C2A H2AA 107.9 . .
C3A C2A H2AB 107.9 . .
C2A C3A H3AA 107.2 . .
C2A C3A H3AB 107.2 . .
H3AA C3A H3AB 106.9 . .
C4A C3A C2A 120.4(10) . .
C4A C3A H3AA 107.2 . .
C4A C3A H3AB 107.2 . .
C3A C4A H4AA 99.5 . .
C3A C4A H4AB 99.5 . .
H4AA C4A H4AB 104.1 . .
C5A C4A C3A 148.8(14) . .
C5A C4A H4AA 99.5 . .
C5A C4A H4AB 99.5 . .
C4A C5A H5AA 99.7 . .
C4A C5A H5AB 99.7 . .
H5AA C5A H5AB 104.1 . .
C6A C5A C4A 148.2(14) . .
C6A C5A H5AA 99.7 . .
C6A C5A H5AB 99.7 . .
C5A C6A H6AA 103.2 . .
C5A C6A H6AB 103.2 . .
C5A C6A C7A 135.8(12) . .
H6AA C6A H6AB 105.2 . .
C7A C6A H6AA 103.2 . .
C7A C6A H6AB 103.2 . .
C6A C7A H7AA 108.5 . .
C6A C7A H7AB 108.5 . .
H7AA C7A H7AB 107.5 . .
C8A C7A C6A 114.9(12) . .
C8A C7A H7AA 108.5 . .
C8A C7A H7AB 108.5 . .
C7A C8A H8AA 109.5 . .
C7A C8A H8AB 109.5 . .
C7A C8A H8AC 109.5 . .
H8AA C8A H8AB 109.5 . .
H8AA C8A H8AC 109.5 . .
H8AB C8A H8AC 109.5 . .
H1BA N1B H1BB 109.5 . .
H1BA N1B H1BC 109.5 . .
H1BB N1B H1BC 109.5 . .
C1B N1B H1BA 109.5 . .
C1B N1B H1BB 109.5 . .
C1B N1B H1BC 109.5 . .
N1B C1B H1BD 110.1 . .
N1B C1B H1BE 110.1 . .
N1B C1B C2B 107.8(10) . .
H1BD C1B H1BE 108.5 . .
C2B C1B H1BD 110.1 . .
C2B C1B H1BE 110.1 . .
C1B C2B H2BA 108.7 . .
C1B C2B H2BB 108.7 . .
C1B C2B C3B 114.2(4) . .
H2BA C2B H2BB 107.6 . .
C3B C2B H2BA 108.7 . .
C3B C2B H2BB 108.7 . .
C2B C3B H3BA 108.7 . .
C2B C3B H3BB 108.7 . .
H3BA C3B H3BB 107.6 . .
C4B C3B C2B 114.2(4) . .
C4B C3B H3BA 108.7 . .
C4B C3B H3BB 108.7 . .
C3B C4B H4BA 108.7 . .
C3B C4B H4BB 108.7 . .
H4BA C4B H4BB 107.6 . .
C5B C4B C3B 114.3(4) . .
C5B C4B H4BA 108.7 . .
C5B C4B H4BB 108.7 . .
C4B C5B H5BA 108.7 . .
C4B C5B H5BB 108.7 . .
C4B C5B C6B 114.2(4) . .
H5BA C5B H5BB 107.6 . .
C6B C5B H5BA 108.7 . .
C6B C5B H5BB 108.7 . .
C5B C6B H6BA 108.7 . .
C5B C6B H6BB 108.7 . .
H6BA C6B H6BB 107.6 . .
C7B C6B C5B 114.2(4) . .
C7B C6B H6BA 108.7 . .
C7B C6B H6BB 108.7 . .
C6B C7B H7BA 108.7 . .
C6B C7B H7BB 108.7 . .
C6B C7B C8B 114.3(5) . .
H7BA C7B H7BB 107.6 . .
C8B C7B H7BA 108.7 . .
C8B C7B H7BB 108.7 . .
C7B C8B H8BA 109.5 . .
C7B C8B H8BB 109.5 . .
C7B C8B H8BC 109.5 . .
H8BA C8B H8BB 109.5 . .
H8BA C8B H8BC 109.5 . .
H8BB C8B H8BC 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.9801 .
O1 C3 1.412(8) .
O2 H2 0.8400 .
O2 C7 1.445(6) .
O3 H3 0.8400 .
O3 C12 1.432(5) .
O4 C24 1.235(5) .
O5 C24 1.260(6) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.507(9) .
C1 C10 1.508(11) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.507(12) .
C3 H3A 1.0000 .
C3 C4 1.535(13) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.502(9) .
C5 H5 1.0000 .
C5 C6 1.482(12) .
C5 C10 1.518(10) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.605(8) .
C7 H7 1.0000 .
C7 C8 1.500(8) .
C8 H8 1.0000 .
C8 C9 1.565(9) .
C8 C14 1.516(7) .
C9 H9 1.0000 .
C9 C10 1.565(7) .
C9 C11 1.492(8) .
C10 C19 1.564(7) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.520(6) .
C12 H12 1.0000 .
C12 C13 1.524(7) .
C13 C14 1.540(6) .
C13 C17 1.560(7) .
C13 C18 1.544(5) .
C14 H14 1.0000 .
C14 C15 1.502(7) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.557(7) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.565(7) .
C17 H17 1.0000 .
C17 C20 1.540(6) .
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 1.526(9) .
C20 C22 1.517(8) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C22 C23 1.562(7) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C23 C24 1.457(7) .
O6 H6C 0.8503 .
O6 H6D 0.8500 .
O7 H7A 0.8501 .
O7 H7B 0.8500 .
N1A H1AA 0.9100 .
N1A H1AB 0.9100 .
N1A H1AC 0.9100 .
N1A C1A 1.490(11) .
C1A H1AD 0.9900 .
C1A H1AE 0.9900 .
C1A C2A 1.501(3) .
C2A H2AA 0.9900 .
C2A H2AB 0.9900 .
C2A C3A 1.501(3) .
C3A H3AA 0.9900 .
C3A H3AB 0.9900 .
C3A C4A 1.501(3) .
C4A H4AA 0.9900 .
C4A H4AB 0.9900 .
C4A C5A 1.499(3) .
C5A H5AA 0.9900 .
C5A H5AB 0.9900 .
C5A C6A 1.499(3) .
C6A H6AA 0.9900 .
C6A H6AB 0.9900 .
C6A C7A 1.500(3) .
C7A H7AA 0.9900 .
C7A H7AB 0.9900 .
C7A C8A 1.499(3) .
C8A H8AA 0.9800 .
C8A H8AB 0.9800 .
C8A H8AC 0.9800 .
N1B H1BA 0.9100 .
N1B H1BB 0.9100 .
N1B H1BC 0.9100 .
N1B C1B 1.491(11) .
C1B H1BD 0.9900 .
C1B H1BE 0.9900 .
C1B C2B 1.500(3) .
C2B H2BA 0.9900 .
C2B H2BB 0.9900 .
C2B C3B 1.500(3) .
C3B H3BA 0.9900 .
C3B H3BB 0.9900 .
C3B C4B 1.500(3) .
C4B H4BA 0.9900 .
C4B H4BB 0.9900 .
C4B C5B 1.500(3) .
C5B H5BA 0.9900 .
C5B H5BB 0.9900 .
C5B C6B 1.501(3) .
C6B H6BA 0.9900 .
C6B H6BB 0.9900 .
C6B C7B 1.499(3) .
C7B H7BA 0.9900 .
C7B H7BB 0.9900 .
C7B C8B 1.500(3) .
C8B H8BA 0.9800 .
C8B H8BB 0.9800 .
C8B H8BC 0.9800 .
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 O7 0.98 1.83 2.809(9) 172.7 . yes
O2 H2 O4 0.84 1.97 2.768(6) 157.6 2_656 yes
O3 H3 O4 0.84 1.89 2.732(5) 178.7 2_646 yes
N1A H1AA O5 0.91 1.84 2.635(12) 144.0 . yes
N1A H1AB O2 0.91 2.31 2.810(11) 114.5 2_646 yes
N1A H1AC O7 0.91 2.21 3.080(13) 160.5 2_656 yes
N1B H1BA O5 0.91 1.96 2.867(15) 170.9 . yes
N1B H1BB O2 0.91 2.17 2.866(13) 133.2 2_646 yes
N1B H1BC O7 0.91 1.61 2.510(15) 171.3 2_656 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 -179.7(6) . . . .
O2 C7 C8 C9 73.2(6) . . . .
O2 C7 C8 C14 -52.5(7) . . . .
O3 C12 C13 C14 -65.1(4) . . . .
O3 C12 C13 C17 48.0(5) . . . .
O3 C12 C13 C18 172.0(3) . . . .
C1 C2 C3 O1 -178.1(6) . . . .
C1 C2 C3 C4 -52.8(7) . . . .
C2 C1 C10 C5 -55.3(7) . . . .
C2 C1 C10 C9 64.1(8) . . . .
C2 C1 C10 C19 -172.5(6) . . . .
C2 C3 C4 C5 50.6(7) . . . .
C3 C4 C5 C6 179.3(5) . . . .
C3 C4 C5 C10 -54.9(8) . . . .
C4 C5 C6 C7 76.0(7) . . . .
C4 C5 C10 C1 54.8(7) . . . .
C4 C5 C10 C9 -69.4(8) . . . .
C4 C5 C10 C19 170.7(6) . . . .
C5 C6 C7 O2 -74.7(7) . . . .
C5 C6 C7 C8 49.2(7) . . . .
C6 C5 C10 C1 -179.7(5) . . . .
C6 C5 C10 C9 56.0(6) . . . .
C6 C5 C10 C19 -63.9(6) . . . .
C6 C7 C8 C9 -47.0(5) . . . .
C6 C7 C8 C14 -172.8(4) . . . .
C7 C8 C9 C10 56.6(5) . . . .
C7 C8 C9 C11 -173.9(4) . . . .
C7 C8 C14 C13 -179.5(4) . . . .
C7 C8 C14 C15 -57.6(6) . . . .
C8 C9 C10 C1 -177.2(5) . . . .
C8 C9 C10 C5 -59.7(6) . . . .
C8 C9 C10 C19 60.3(7) . . . .
C8 C9 C11 C12 46.3(5) . . . .
C8 C14 C15 C16 -159.8(4) . . . .
C9 C8 C14 C13 54.5(5) . . . .
C9 C8 C14 C15 176.5(4) . . . .
C9 C11 C12 O3 69.6(6) . . . .
C9 C11 C12 C13 -53.0(5) . . . .
C10 C1 C2 C3 58.3(8) . . . .
C10 C5 C6 C7 -53.7(6) . . . .
C10 C9 C11 C12 176.5(4) . . . .
C11 C9 C10 C1 52.5(6) . . . .
C11 C9 C10 C5 170.0(5) . . . .
C11 C9 C10 C19 -70.0(7) . . . .
C11 C12 C13 C14 58.0(5) . . . .
C11 C12 C13 C17 171.1(4) . . . .
C11 C12 C13 C18 -64.8(5) . . . .
C12 C13 C14 C8 -60.9(5) . . . .
C12 C13 C14 C15 169.1(3) . . . .
C12 C13 C17 C16 -156.4(4) . . . .
C12 C13 C17 C20 78.1(5) . . . .
C13 C14 C15 C16 -33.6(4) . . . .
C13 C17 C20 C21 -60.1(5) . . . .
C13 C17 C20 C22 177.2(4) . . . .
C14 C8 C9 C10 -175.7(4) . . . .
C14 C8 C9 C11 -46.3(5) . . . .
C14 C13 C17 C16 -39.5(4) . . . .
C14 C13 C17 C20 -165.0(4) . . . .
C14 C15 C16 C17 8.2(4) . . . .
C15 C16 C17 C13 19.7(4) . . . .
C15 C16 C17 C20 146.9(4) . . . .
C16 C17 C20 C21 -179.4(4) . . . .
C16 C17 C20 C22 57.9(5) . . . .
C17 C13 C14 C8 176.1(4) . . . .
C17 C13 C14 C15 46.1(4) . . . .
C17 C20 C22 C23 -168.2(4) . . . .
C18 C13 C14 C8 60.5(5) . . . .
C18 C13 C14 C15 -69.4(5) . . . .
C18 C13 C17 C16 78.8(4) . . . .
C18 C13 C17 C20 -46.7(5) . . . .
C20 C22 C23 C24 -161.1(5) . . . .
C21 C20 C22 C23 66.8(6) . . . .
C22 C23 C24 O4 2.9(9) . . . .
C22 C23 C24 O5 170.7(5) . . . .
N1A C1A C2A C3A 76.0(17) . . . .
C1A C2A C3A C4A 176.7(14) . . . .
C2A C3A C4A C5A -131(3) . . . .
C3A C4A C5A C6A -135(3) . . . .
C4A C5A C6A C7A -178(2) . . . .
C5A C6A C7A C8A 158.9(18) . . . .
N1B C1B C2B C3B 175.0(13) . . . .
C1B C2B C3B C4B 167.9(12) . . . .
C2B C3B C4B C5B 109.4(12) . . . .
C3B C4B C5B C6B 119.5(8) . . . .
C4B C5B C6B C7B 128.5(14) . . . .
C5B C6B C7B C8B 179.5(15) . . . .

_cod_database_fobs_code 4519429
