#------------------------------------------------------------------------------
#$Date: 2020-07-04 08:14:11 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253756 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243462.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243462
loop_
_publ_author_name
'Twamley, Brendan'
'O'Boyle, Niamh M.'
'Meegan, Mary J.'
_publ_section_title
;
 Azetidin-2-ones: structures of antimitotic compounds based on the
 1-(3,4,5-trimethoxyphenyl)azetidin-2-one core
;
_journal_coeditor_code           ZL2789
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1187
_journal_page_last               1194
_journal_paper_doi               10.1107/S2056989020008555
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C23 H23 N O6'
_chemical_formula_moiety         'C23 H23 N O6'
_chemical_formula_sum            'C23 H23 N O6'
_chemical_formula_weight         409.42
_chemical_name_systematic
;
3-(Furan-2-yl)-4-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0705(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.794(2)
_cell_length_b                   9.1396(9)
_cell_length_c                   23.161(2)
_cell_measurement_reflns_used    9712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.24
_cell_volume                     4112.1(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            104383
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.095
_diffrn_reflns_theta_min         1.792
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.249
_refine_ls_extinction_coef       0.00110(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         8072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0562
_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)+(0.0339P)²+3.2926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                5950
_reflns_number_total             8072
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2789sup1.cif
_cod_data_source_block           2
_cod_original_cell_volume        4112.0(7)
_cod_database_code               2243462
_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.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.47248(11) 0.3915(2) 0.20698(9) 0.0191(4) Uani d 1 . .
C C3 0.54420(10) 0.3731(2) 0.19170(9) 0.0197(4) Uani d 1 . .
H H3 0.567145 0.469890 0.189674 0.024 Uiso calc 1 . .
C C4 0.56531(10) 0.3031(2) 0.25452(9) 0.0192(4) Uani d 1 . .
H H4 0.573621 0.195483 0.252203 0.023 Uiso calc 1 . .
C C5 0.46055(10) 0.3049(2) 0.30884(9) 0.0190(4) Uani d 1 . .
C C6 0.49630(10) 0.2258(2) 0.35596(9) 0.0186(4) Uani d 1 . .
H H6 0.542512 0.196365 0.356850 0.022 Uiso calc 1 . .
C C7 0.46335(11) 0.1905(2) 0.40192(9) 0.0200(5) Uani d 1 . .
C C8 0.39586(11) 0.2346(2) 0.40053(9) 0.0219(5) Uani d 1 . .
C C9 0.36241(10) 0.3206(2) 0.35366(9) 0.0226(5) Uani d 1 . .
C C10 0.39389(10) 0.3545(2) 0.30683(9) 0.0208(5) Uani d 1 . .
H H10 0.370564 0.410008 0.274372 0.025 Uiso calc 1 . .
C C12 0.56294(11) 0.0660(2) 0.45217(10) 0.0265(5) Uani d 1 . .
H H12A 0.592766 0.151371 0.451573 0.040 Uiso calc 1 . .
H H12B 0.564784 0.003971 0.417994 0.040 Uiso calc 1 . .
H H12C 0.578719 0.010074 0.488339 0.040 Uiso calc 1 . .
C C14 0.36424(13) 0.2922(3) 0.49058(10) 0.0351(6) Uani d 1 . .
H H14A 0.412296 0.307489 0.509826 0.053 Uiso calc 1 . .
H H14B 0.338187 0.254135 0.519289 0.053 Uiso calc 1 . .
H H14C 0.344203 0.385328 0.474793 0.053 Uiso calc 1 . .
C C16 0.26548(12) 0.4684(3) 0.31493(11) 0.0346(6) Uani d 1 . .
H H16A 0.294965 0.554720 0.315525 0.052 Uiso calc 1 . .
H H16B 0.221075 0.497658 0.324055 0.052 Uiso calc 1 . .
H H16C 0.258105 0.423415 0.275804 0.052 Uiso calc 1 . .
C C18 0.62031(10) 0.3758(2) 0.29826(9) 0.0190(4) Uani d 1 . .
C C19 0.61448(10) 0.5225(2) 0.31302(9) 0.0220(5) Uani d 1 . .
H H19 0.575634 0.577145 0.294165 0.026 Uiso calc 1 . .
C C20 0.66395(11) 0.5896(2) 0.35439(10) 0.0240(5) Uani d 1 . .
H H20 0.658855 0.689345 0.364289 0.029 Uiso calc 1 . .
C C21 0.72133(11) 0.5111(2) 0.38163(9) 0.0230(5) Uani d 1 . .
C C22 0.72891(11) 0.3664(2) 0.36712(10) 0.0267(5) Uani d 1 . .
H H22 0.768502 0.312916 0.385176 0.032 Uiso calc 1 . .
C C23 0.67788(11) 0.2997(2) 0.32570(10) 0.0248(5) Uani d 1 . .
H H23 0.682772 0.199631 0.316130 0.030 Uiso calc 1 . .
C C25 0.83308(12) 0.5203(3) 0.44327(11) 0.0376(6) Uani d 1 . .
H H25A 0.862093 0.586967 0.470516 0.056 Uiso calc 1 . .
H H25B 0.854927 0.500759 0.409499 0.056 Uiso calc 1 . .
H H25C 0.827427 0.428161 0.463481 0.056 Uiso calc 1 . .
C C26 0.54927(10) 0.2819(2) 0.14043(9) 0.0204(5) Uani d 1 . .
C C28 0.52460(12) 0.0841(2) 0.08710(10) 0.0274(5) Uani d 1 . .
H H28 0.506039 -0.008412 0.073696 0.033 Uiso calc 1 . .
C C29 0.56570(11) 0.1641(2) 0.06038(10) 0.0276(5) Uani d 1 . .
H H29 0.580973 0.140432 0.025057 0.033 Uiso calc 1 . .
C C30 0.58228(11) 0.2926(2) 0.09538(9) 0.0257(5) Uani d 1 . .
H H30 0.611211 0.370625 0.088044 0.031 Uiso calc 1 . .
N N1 0.49383(8) 0.33475(18) 0.26178(7) 0.0186(4) Uani d 1 . .
O O11 0.49377(7) 0.11359(16) 0.45011(6) 0.0243(3) Uani d 1 . .
O O13 0.36136(7) 0.18958(17) 0.44377(6) 0.0274(4) Uani d 1 . .
O O15 0.29799(7) 0.36539(18) 0.35776(7) 0.0299(4) Uani d 1 . .
O O17 0.41698(7) 0.43656(16) 0.18205(6) 0.0233(3) Uani d 1 . .
O O24 0.76701(7) 0.58592(17) 0.42327(7) 0.0283(4) Uani d 1 . .
O O27 0.51283(7) 0.15338(16) 0.13638(6) 0.0262(4) Uani d 1 . .
C C2A 0.01341(11) 0.9003(2) 0.19312(10) 0.0235(5) Uani d 1 . .
C C3A -0.06450(10) 0.8773(2) 0.17615(9) 0.0238(5) Uani d 1 . .
H H3A -0.089512 0.972865 0.172892 0.029 Uiso calc 1 . .
C C4A -0.05884(10) 0.8100(2) 0.23922(9) 0.0221(5) Uani d 1 . .
H H4A -0.064913 0.701345 0.237090 0.027 Uiso calc 1 . .
C C5A 0.06718(10) 0.8324(2) 0.29907(9) 0.0222(5) Uani d 1 . .
C C6A 0.05023(11) 0.7687(2) 0.34848(10) 0.0246(5) Uani d 1 . .
H H6A 0.004496 0.736727 0.348188 0.030 Uiso calc 1 . .
C C7A 0.10090(11) 0.7520(2) 0.39857(10) 0.0263(5) Uani d 1 . .
C C8A 0.16773(11) 0.7963(2) 0.39858(10) 0.0276(5) Uani d 1 . .
C C9A 0.18367(11) 0.8617(2) 0.34839(10) 0.0272(5) Uani d 1 . .
C C10A 0.13357(10) 0.8799(2) 0.29815(10) 0.0243(5) Uani d 1 . .
H H10A 0.144426 0.923947 0.263904 0.029 Uiso calc 1 . .
C C12A 0.01940(13) 0.6680(3) 0.45433(11) 0.0419(6) Uani d 1 . .
H H12D 0.017145 0.638564 0.494599 0.063 Uiso calc 1 . .
H H12E 0.000957 0.589440 0.427025 0.063 Uiso calc 1 . .
H H12F -0.007888 0.757043 0.444148 0.063 Uiso calc 1 . .
C C14A 0.25700(12) 0.6580(3) 0.45336(11) 0.0379(6) Uani d 1 . .
H H14D 0.285078 0.660480 0.422828 0.057 Uiso calc 1 . .
H H14E 0.226759 0.572192 0.447434 0.057 Uiso calc 1 . .
H H14F 0.287129 0.652246 0.492163 0.057 Uiso calc 1 . .
C C16A 0.26520(12) 0.9975(3) 0.30756(12) 0.0381(6) Uani d 1 . .
H H16D 0.257857 0.942833 0.270470 0.057 Uiso calc 1 . .
H H16E 0.313269 1.029574 0.317547 0.057 Uiso calc 1 . .
H H16F 0.234848 1.083105 0.303271 0.057 Uiso calc 1 . .
C C18A -0.09903(10) 0.8755(2) 0.28105(9) 0.0214(5) Uani d 1 . .
C C19A -0.09323(11) 1.0232(2) 0.29593(11) 0.0289(5) Uani d 1 . .
H H19A -0.064140 1.084194 0.278196 0.035 Uiso calc 1 . .
C C20A -0.12873(11) 1.0823(2) 0.33575(11) 0.0312(6) Uani d 1 . .
H H20A -0.124086 1.183340 0.345306 0.037 Uiso calc 1 . .
C C21A -0.17135(11) 0.9945(2) 0.36199(10) 0.0246(5) Uani d 1 . .
C C22A -0.17905(11) 0.8480(2) 0.34707(10) 0.0243(5) Uani d 1 . .
H H22A -0.209307 0.787966 0.363932 0.029 Uiso calc 1 . .
C C23A -0.14226(10) 0.7898(2) 0.30737(9) 0.0233(5) Uani d 1 . .
H H23A -0.146783 0.688701 0.297950 0.028 Uiso calc 1 . .
C C25A -0.25363(12) 0.9820(3) 0.42498(11) 0.0310(5) Uani d 1 . .
H H25D -0.233899 0.890512 0.442831 0.046 Uiso calc 1 . .
H H25E -0.292126 0.959781 0.392753 0.046 Uiso calc 1 . .
H H25F -0.270186 1.041064 0.454722 0.046 Uiso calc 1 . .
C C26A -0.09111(11) 0.7821(2) 0.12535(10) 0.0250(5) Uani d 1 . .
C C28A -0.17691(13) 0.6706(3) 0.06858(11) 0.0385(6) Uani d 1 . .
H H28A -0.222141 0.639372 0.051626 0.046 Uiso calc 1 . .
C C29A -0.11983(13) 0.6254(3) 0.05174(11) 0.0361(6) Uani d 1 . .
H H29A -0.116986 0.558946 0.020772 0.043 Uiso calc 1 . .
C C30A -0.06364(13) 0.6962(3) 0.08924(11) 0.0356(6) Uani d 1 . .
H H30A -0.016085 0.684579 0.088640 0.043 Uiso calc 1 . .
N N1A 0.01505(8) 0.84972(19) 0.24877(8) 0.0220(4) Uani d 1 . .
O O11A 0.08906(8) 0.69564(19) 0.45029(7) 0.0363(4) Uani d 1 . .
O O13A 0.21642(8) 0.78714(19) 0.44995(7) 0.0371(4) Uani d 1 . .
O O15A 0.25015(8) 0.90595(19) 0.35308(7) 0.0346(4) Uani d 1 . .
O O17A 0.05790(7) 0.94552(17) 0.16854(7) 0.0293(4) Uani d 1 . .
O O24A -0.20227(8) 1.06133(17) 0.40262(7) 0.0320(4) Uani d 1 . .
O O27A -0.16117(8) 0.7684(2) 0.11372(7) 0.0379(4) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C2 C3 . . 92.16(16) ?
O17 C2 C3 . . 136.14(19) ?
O17 C2 N1 . . 131.70(19) ?
C2 C3 H3 . . 111.2 ?
C2 C3 C4 . . 85.67(15) ?
C4 C3 H3 . . 111.2 ?
C26 C3 C2 . . 117.24(17) ?
C26 C3 H3 . . 111.2 ?
C26 C3 C4 . . 118.06(17) ?
C3 C4 H4 . . 111.6 ?
C18 C4 C3 . . 118.46(17) ?
C18 C4 H4 . . 111.6 ?
N1 C4 C3 . . 86.31(14) ?
N1 C4 H4 . . 111.6 ?
N1 C4 C18 . . 115.00(17) ?
C6 C5 C10 . . 122.39(19) ?
C6 C5 N1 . . 117.93(18) ?
C10 C5 N1 . . 119.68(19) ?
C5 C6 H6 . . 120.6 ?
C5 C6 C7 . . 118.77(19) ?
C7 C6 H6 . . 120.6 ?
C6 C7 C8 . . 120.36(19) ?
O11 C7 C6 . . 123.42(19) ?
O11 C7 C8 . . 116.21(18) ?
C7 C8 C9 . . 119.36(18) ?
O13 C8 C7 . . 120.31(19) ?
O13 C8 C9 . . 120.29(18) ?
C10 C9 C8 . . 121.06(19) ?
O15 C9 C8 . . 115.18(18) ?
O15 C9 C10 . . 123.8(2) ?
C5 C10 H10 . . 121.0 ?
C9 C10 C5 . . 117.9(2) ?
C9 C10 H10 . . 121.0 ?
H12A C12 H12B . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O11 C12 H12A . . 109.5 ?
O11 C12 H12B . . 109.5 ?
O11 C12 H12C . . 109.5 ?
H14A C14 H14B . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O13 C14 H14A . . 109.5 ?
O13 C14 H14B . . 109.5 ?
O13 C14 H14C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O15 C16 H16A . . 109.5 ?
O15 C16 H16B . . 109.5 ?
O15 C16 H16C . . 109.5 ?
C19 C18 C4 . . 120.71(18) ?
C23 C18 C4 . . 121.15(19) ?
C23 C18 C19 . . 118.1(2) ?
C18 C19 H19 . . 119.4 ?
C20 C19 C18 . . 121.22(19) ?
C20 C19 H19 . . 119.4 ?
C19 C20 H20 . . 120.1 ?
C19 C20 C21 . . 119.8(2) ?
C21 C20 H20 . . 120.1 ?
C22 C21 C20 . . 120.1(2) ?
O24 C21 C20 . . 115.69(19) ?
O24 C21 C22 . . 124.15(19) ?
C21 C22 H22 . . 120.4 ?
C21 C22 C23 . . 119.3(2) ?
C23 C22 H22 . . 120.4 ?
C18 C23 C22 . . 121.4(2) ?
C18 C23 H23 . . 119.3 ?
C22 C23 H23 . . 119.3 ?
H25A C25 H25B . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
O24 C25 H25A . . 109.5 ?
O24 C25 H25B . . 109.5 ?
O24 C25 H25C . . 109.5 ?
C30 C26 C3 . . 135.1(2) ?
C30 C26 O27 . . 109.77(18) ?
O27 C26 C3 . . 115.08(17) ?
C29 C28 H28 . . 124.7 ?
C29 C28 O27 . . 110.6(2) ?
O27 C28 H28 . . 124.7 ?
C28 C29 H29 . . 126.8 ?
C28 C29 C30 . . 106.4(2) ?
C30 C29 H29 . . 126.8 ?
C26 C30 C29 . . 106.8(2) ?
C26 C30 H30 . . 126.6 ?
C29 C30 H30 . . 126.6 ?
C2 N1 C4 . . 95.79(15) ?
C2 N1 C5 . . 133.62(17) ?
C5 N1 C4 . . 130.46(17) ?
C7 O11 C12 . . 117.12(16) ?
C8 O13 C14 . . 113.77(17) ?
C9 O15 C16 . . 116.97(17) ?
C21 O24 C25 . . 117.15(18) ?
C28 O27 C26 . . 106.42(16) ?
N1A C2A C3A . . 92.05(16) ?
O17A C2A C3A . . 135.6(2) ?
O17A C2A N1A . . 132.3(2) ?
C2A C3A H3A . . 111.0 ?
C2A C3A C4A . . 85.79(15) ?
C4A C3A H3A . . 111.0 ?
C26A C3A C2A . . 118.24(18) ?
C26A C3A H3A . . 111.0 ?
C26A C3A C4A . . 117.50(18) ?
C3A C4A H4A . . 110.9 ?
C18A C4A C3A . . 119.68(18) ?
C18A C4A H4A . . 110.9 ?
N1A C4A C3A . . 86.26(15) ?
N1A C4A H4A . . 110.9 ?
N1A C4A C18A . . 116.01(17) ?
C6A C5A C10A . . 121.7(2) ?
C6A C5A N1A . . 118.44(18) ?
C10A C5A N1A . . 119.8(2) ?
C5A C6A H6A . . 120.4 ?
C5A C6A C7A . . 119.2(2) ?
C7A C6A H6A . . 120.4 ?
C8A C7A C6A . . 120.3(2) ?
O11A C7A C6A . . 123.8(2) ?
O11A C7A C8A . . 115.8(2) ?
C7A C8A C9A . . 119.6(2) ?
O13A C8A C7A . . 119.4(2) ?
O13A C8A C9A . . 120.7(2) ?
C10A C9A C8A . . 120.7(2) ?
O15A C9A C8A . . 115.5(2) ?
O15A C9A C10A . . 123.8(2) ?
C5A C10A H10A . . 120.8 ?
C9A C10A C5A . . 118.4(2) ?
C9A C10A H10A . . 120.8 ?
H12D C12A H12E . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
O11A C12A H12D . . 109.5 ?
O11A C12A H12E . . 109.5 ?
O11A C12A H12F . . 109.5 ?
H14D C14A H14E . . 109.5 ?
H14D C14A H14F . . 109.5 ?
H14E C14A H14F . . 109.5 ?
O13A C14A H14D . . 109.5 ?
O13A C14A H14E . . 109.5 ?
O13A C14A H14F . . 109.5 ?
H16D C16A H16E . . 109.5 ?
H16D C16A H16F . . 109.5 ?
H16E C16A H16F . . 109.5 ?
O15A C16A H16D . . 109.5 ?
O15A C16A H16E . . 109.5 ?
O15A C16A H16F . . 109.5 ?
C19A C18A C4A . . 121.42(19) ?
C23A C18A C4A . . 120.67(19) ?
C23A C18A C19A . . 117.9(2) ?
C18A C19A H19A . . 119.3 ?
C20A C19A C18A . . 121.3(2) ?
C20A C19A H19A . . 119.3 ?
C19A C20A H20A . . 120.0 ?
C19A C20A C21A . . 120.0(2) ?
C21A C20A H20A . . 120.0 ?
C22A C21A C20A . . 119.8(2) ?
O24A C21A C20A . . 115.8(2) ?
O24A C21A C22A . . 124.3(2) ?
C21A C22A H22A . . 120.3 ?
C21A C22A C23A . . 119.4(2) ?
C23A C22A H22A . . 120.3 ?
C18A C23A H23A . . 119.2 ?
C22A C23A C18A . . 121.6(2) ?
C22A C23A H23A . . 119.2 ?
H25D C25A H25E . . 109.5 ?
H25D C25A H25F . . 109.5 ?
H25E C25A H25F . . 109.5 ?
O24A C25A H25D . . 109.5 ?
O24A C25A H25E . . 109.5 ?
O24A C25A H25F . . 109.5 ?
C30A C26A C3A . . 136.0(2) ?
C30A C26A O27A . . 110.0(2) ?
O27A C26A C3A . . 113.85(18) ?
C29A C28A H28A . . 124.9 ?
C29A C28A O27A . . 110.3(2) ?
O27A C28A H28A . . 124.9 ?
C28A C29A H29A . . 126.7 ?
C28A C29A C30A . . 106.7(2) ?
C30A C29A H29A . . 126.7 ?
C26A C30A C29A . . 106.5(2) ?
C26A C30A H30A . . 126.8 ?
C29A C30A H30A . . 126.8 ?
C2A N1A C4A . . 95.65(16) ?
C2A N1A C5A . . 134.43(18) ?
C5A N1A C4A . . 129.87(17) ?
C7A O11A C12A . . 117.18(18) ?
C8A O13A C14A . . 113.03(18) ?
C9A O15A C16A . . 116.93(18) ?
C21A O24A C25A . . 118.01(17) ?
C28A O27A C26A . . 106.54(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 C3 . 1.537(3) ?
C2 N1 . 1.361(3) ?
C2 O17 . 1.211(2) ?
C3 H3 . 1.0000 ?
C3 C4 . 1.571(3) ?
C3 C26 . 1.469(3) ?
C4 H4 . 1.0000 ?
C4 C18 . 1.493(3) ?
C4 N1 . 1.485(2) ?
C5 C6 . 1.384(3) ?
C5 C10 . 1.388(3) ?
C5 N1 . 1.404(3) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.389(3) ?
C7 C8 . 1.390(3) ?
C7 O11 . 1.358(2) ?
C8 C9 . 1.399(3) ?
C8 O13 . 1.379(2) ?
C9 C10 . 1.386(3) ?
C9 O15 . 1.360(2) ?
C10 H10 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C12 O11 . 1.429(3) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C14 O13 . 1.426(3) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C16 O15 . 1.428(3) ?
C18 C19 . 1.394(3) ?
C18 C23 . 1.382(3) ?
C19 H19 . 0.9500 ?
C19 C20 . 1.376(3) ?
C20 H20 . 0.9500 ?
C20 C21 . 1.388(3) ?
C21 C22 . 1.380(3) ?
C21 O24 . 1.371(3) ?
C22 H22 . 0.9500 ?
C22 C23 . 1.393(3) ?
C23 H23 . 0.9500 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C25 O24 . 1.433(3) ?
C26 C30 . 1.337(3) ?
C26 O27 . 1.373(2) ?
C28 H28 . 0.9500 ?
C28 C29 . 1.331(3) ?
C28 O27 . 1.364(3) ?
C29 H29 . 0.9500 ?
C29 C30 . 1.429(3) ?
C30 H30 . 0.9500 ?
C2A C3A . 1.531(3) ?
C2A N1A . 1.364(3) ?
C2A O17A . 1.209(3) ?
C3A H3A . 1.0000 ?
C3A C4A . 1.569(3) ?
C3A C26A . 1.477(3) ?
C4A H4A . 1.0000 ?
C4A C18A . 1.492(3) ?
C4A N1A . 1.482(3) ?
C5A C6A . 1.382(3) ?
C5A C10A . 1.388(3) ?
C5A N1A . 1.409(3) ?
C6A H6A . 0.9500 ?
C6A C7A . 1.389(3) ?
C7A C8A . 1.383(3) ?
C7A O11A . 1.365(3) ?
C8A C9A . 1.396(3) ?
C8A O13A . 1.383(3) ?
C9A C10A . 1.386(3) ?
C9A O15A . 1.361(3) ?
C10A H10A . 0.9500 ?
C12A H12D . 0.9800 ?
C12A H12E . 0.9800 ?
C12A H12F . 0.9800 ?
C12A O11A . 1.422(3) ?
C14A H14D . 0.9800 ?
C14A H14E . 0.9800 ?
C14A H14F . 0.9800 ?
C14A O13A . 1.421(3) ?
C16A H16D . 0.9800 ?
C16A H16E . 0.9800 ?
C16A H16F . 0.9800 ?
C16A O15A . 1.422(3) ?
C18A C19A . 1.392(3) ?
C18A C23A . 1.385(3) ?
C19A H19A . 0.9500 ?
C19A C20A . 1.373(3) ?
C20A H20A . 0.9500 ?
C20A C21A . 1.386(3) ?
C21A C22A . 1.383(3) ?
C21A O24A . 1.362(3) ?
C22A H22A . 0.9500 ?
C22A C23A . 1.384(3) ?
C23A H23A . 0.9500 ?
C25A H25D . 0.9800 ?
C25A H25E . 0.9800 ?
C25A H25F . 0.9800 ?
C25A O24A . 1.425(3) ?
C26A C30A . 1.336(3) ?
C26A O27A . 1.367(3) ?
C28A H28A . 0.9500 ?
C28A C29A . 1.330(4) ?
C28A O27A . 1.365(3) ?
C29A H29A . 0.9500 ?
C29A C30A . 1.428(3) ?
C30A H30A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10 O17 . 0.95 2.50 3.103(3) 121.8 n
C12 H12C O11 3_656 0.98 2.48 3.171(3) 127.2 n
C12 H12C O13 3_656 0.98 2.55 3.482(3) 159.3 n
C22 H22 O24A 1_645 0.95 2.39 3.143(3) 136.3 n
C10A H10A O17A . 0.95 2.53 3.144(3) 122.6 n
C22A H22A O24 1_455 0.95 2.40 3.274(3) 152.6 n
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C3 C4 C18 . . . . -118.34(18) ?
C2 C3 C4 N1 . . . . -1.80(14) ?
C2 C3 C26 C30 . . . . 137.0(2) ?
C2 C3 C26 O27 . . . . -43.8(2) ?
C3 C2 N1 C4 . . . . -2.08(16) ?
C3 C2 N1 C5 . . . . -178.1(2) ?
C3 C4 C18 C19 . . . . 55.5(3) ?
C3 C4 C18 C23 . . . . -125.2(2) ?
C3 C4 N1 C2 . . . . 2.04(16) ?
C3 C4 N1 C5 . . . . 178.3(2) ?
C3 C26 C30 C29 . . . . 179.5(2) ?
C3 C26 O27 C28 . . . . -179.18(17) ?
C4 C3 C26 C30 . . . . -122.7(3) ?
C4 C3 C26 O27 . . . . 56.4(2) ?
C4 C18 C19 C20 . . . . 178.27(19) ?
C4 C18 C23 C22 . . . . -179.13(19) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
C5 C6 C7 O11 . . . . -179.94(18) ?
C6 C5 C10 C9 . . . . -1.1(3) ?
C6 C5 N1 C2 . . . . 170.6(2) ?
C6 C5 N1 C4 . . . . -4.3(3) ?
C6 C7 C8 C9 . . . . -2.8(3) ?
C6 C7 C8 O13 . . . . 174.78(18) ?
C6 C7 O11 C12 . . . . -1.0(3) ?
C7 C8 C9 C10 . . . . 4.2(3) ?
C7 C8 C9 O15 . . . . -176.39(18) ?
C7 C8 O13 C14 . . . . 95.2(2) ?
C8 C7 O11 C12 . . . . 179.44(18) ?
C8 C9 C10 C5 . . . . -2.2(3) ?
C8 C9 O15 C16 . . . . 172.20(19) ?
C9 C8 O13 C14 . . . . -87.2(2) ?
C10 C5 C6 C7 . . . . 2.4(3) ?
C10 C5 N1 C2 . . . . -9.4(3) ?
C10 C5 N1 C4 . . . . 175.72(19) ?
C10 C9 O15 C16 . . . . -8.4(3) ?
C18 C4 N1 C2 . . . . 121.84(18) ?
C18 C4 N1 C5 . . . . -61.9(3) ?
C18 C19 C20 C21 . . . . 0.8(3) ?
C19 C18 C23 C22 . . . . 0.1(3) ?
C19 C20 C21 C22 . . . . 0.3(3) ?
C19 C20 C21 O24 . . . . -178.46(19) ?
C20 C21 C22 C23 . . . . -1.1(3) ?
C20 C21 O24 C25 . . . . -167.21(19) ?
C21 C22 C23 C18 . . . . 0.9(3) ?
C22 C21 O24 C25 . . . . 14.1(3) ?
C23 C18 C19 C20 . . . . -1.0(3) ?
C26 C3 C4 C18 . . . . 123.0(2) ?
C26 C3 C4 N1 . . . . -120.48(18) ?
C28 C29 C30 C26 . . . . -0.8(3) ?
C29 C28 O27 C26 . . . . -0.7(2) ?
C30 C26 O27 C28 . . . . 0.2(2) ?
N1 C2 C3 C4 . . . . 1.96(15) ?
N1 C2 C3 C26 . . . . 121.41(19) ?
N1 C4 C18 C19 . . . . -44.4(3) ?
N1 C4 C18 C23 . . . . 134.9(2) ?
N1 C5 C6 C7 . . . . -177.62(18) ?
N1 C5 C10 C9 . . . . 178.89(18) ?
O11 C7 C8 C9 . . . . 176.79(18) ?
O11 C7 C8 O13 . . . . -5.6(3) ?
O13 C8 C9 C10 . . . . -173.46(19) ?
O13 C8 C9 O15 . . . . 6.0(3) ?
O15 C9 C10 C5 . . . . 178.39(19) ?
O17 C2 C3 C4 . . . . -177.5(3) ?
O17 C2 C3 C26 . . . . -58.0(3) ?
O17 C2 N1 C4 . . . . 177.4(2) ?
O17 C2 N1 C5 . . . . 1.3(4) ?
O24 C21 C22 C23 . . . . 177.50(19) ?
O27 C26 C30 C29 . . . . 0.4(2) ?
O27 C28 C29 C30 . . . . 0.9(3) ?
C2A C3A C4A C18A . . . . 121.34(19) ?
C2A C3A C4A N1A . . . . 3.40(15) ?
C2A C3A C26A C30A . . . . 5.5(4) ?
C2A C3A C26A O27A . . . . 180.00(18) ?
C3A C2A N1A C4A . . . . 3.91(17) ?
C3A C2A N1A C5A . . . . -178.4(2) ?
C3A C4A C18A C19A . . . . -55.5(3) ?
C3A C4A C18A C23A . . . . 126.0(2) ?
C3A C4A N1A C2A . . . . -3.82(17) ?
C3A C4A N1A C5A . . . . 178.3(2) ?
C3A C26A C30A C29A . . . . 175.6(2) ?
C3A C26A O27A C28A . . . . -176.12(19) ?
C4A C3A C26A C30A . . . . -95.2(3) ?
C4A C3A C26A O27A . . . . 79.3(2) ?
C4A C18A C19A C20A . . . . -178.1(2) ?
C4A C18A C23A C22A . . . . 178.84(19) ?
C5A C6A C7A C8A . . . . -1.1(3) ?
C5A C6A C7A O11A . . . . 177.4(2) ?
C6A C5A C10A C9A . . . . 0.3(3) ?
C6A C5A N1A C2A . . . . -176.6(2) ?
C6A C5A N1A C4A . . . . 0.4(3) ?
C6A C7A C8A C9A . . . . 1.7(3) ?
C6A C7A C8A O13A . . . . 176.0(2) ?
C6A C7A O11A C12A . . . . -7.1(3) ?
C7A C8A C9A C10A . . . . -1.3(3) ?
C7A C8A C9A O15A . . . . 178.0(2) ?
C7A C8A O13A C14A . . . . 96.8(2) ?
C8A C7A O11A C12A . . . . 171.5(2) ?
C8A C9A C10A C5A . . . . 0.4(3) ?
C8A C9A O15A C16A . . . . -168.2(2) ?
C9A C8A O13A C14A . . . . -89.0(3) ?
C10A C5A C6A C7A . . . . 0.1(3) ?
C10A C5A N1A C2A . . . . 3.8(4) ?
C10A C5A N1A C4A . . . . -179.3(2) ?
C10A C9A O15A C16A . . . . 11.1(3) ?
C18A C4A N1A C2A . . . . -125.18(19) ?
C18A C4A N1A C5A . . . . 57.0(3) ?
C18A C19A C20A C21A . . . . 0.0(4) ?
C19A C18A C23A C22A . . . . 0.3(3) ?
C19A C20A C21A C22A . . . . -1.3(3) ?
C19A C20A C21A O24A . . . . 177.5(2) ?
C20A C21A C22A C23A . . . . 2.0(3) ?
C20A C21A O24A C25A . . . . 171.6(2) ?
C21A C22A C23A C18A . . . . -1.5(3) ?
C22A C21A O24A C25A . . . . -9.7(3) ?
C23A C18A C19A C20A . . . . 0.5(3) ?
C26A C3A C4A C18A . . . . -118.9(2) ?
C26A C3A C4A N1A . . . . 123.18(19) ?
C28A C29A C30A C26A . . . . -1.4(3) ?
C29A C28A O27A C26A . . . . -0.7(3) ?
C30A C26A O27A C28A . . . . -0.2(3) ?
N1A C2A C3A C4A . . . . -3.69(16) ?
N1A C2A C3A C26A . . . . -122.8(2) ?
N1A C4A C18A C19A . . . . 45.7(3) ?
N1A C4A C18A C23A . . . . -132.8(2) ?
N1A C5A C6A C7A . . . . -179.48(19) ?
N1A C5A C10A C9A . . . . 179.85(19) ?
O11A C7A C8A C9A . . . . -176.9(2) ?
O11A C7A C8A O13A . . . . -2.7(3) ?
O13A C8A C9A C10A . . . . -175.5(2) ?
O13A C8A C9A O15A . . . . 3.8(3) ?
O15A C9A C10A C5A . . . . -178.9(2) ?
O17A C2A C3A C4A . . . . 176.5(3) ?
O17A C2A C3A C26A . . . . 57.4(3) ?
O17A C2A N1A C4A . . . . -176.3(2) ?
O17A C2A N1A C5A . . . . 1.4(4) ?
O24A C21A C22A C23A . . . . -176.6(2) ?
O27A C26A C30A C29A . . . . 1.0(3) ?
O27A C28A C29A C30A . . . . 1.3(3) ?

_cod_database_fobs_code 2243462
