#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228364.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_2228364
loop_
_publ_author_name
'Ngaini, Zainab'
'Fadzillah, Siti Muhaini Haris'
'Hussain, Hasnain'
'Razak, Ibrahim Abdul'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-1-[4-(Hexyloxy)phenyl]-3-(3-hydroxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           HB5741
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3275
_journal_page_last               o3276
_journal_paper_doi               10.1107/S1600536810047768
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H24 O3'
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_chemical_name_systematic
;
(E)-1-[4-(Hexyloxy)phenyl]-3-(3-hydroxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.226(2)
_cell_angle_beta                 93.740(2)
_cell_angle_gamma                93.038(2)
_cell_formula_units_Z            4
_cell_length_a                   7.6053(3)
_cell_length_b                   13.7328(5)
_cell_length_c                   17.3769(7)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.69
_cell_volume                     1742.80(12)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'π and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36519
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.767
_exptl_crystal_size_mid          0.438
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         10044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0965P)²+0.6952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1883
_reflns_number_gt                6371
_reflns_number_total             10044
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5741.cif
_cod_data_source_block           I
_cod_database_code               2228364
_cod_database_fobs_code          2228364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A -0.04558(17) -0.32446(10) 0.74767(8) 0.0222(3) Uani d . 1 . .
O O2A 0.17874(17) 0.08611(9) 0.57096(7) 0.0229(3) Uani d . 1 . .
O O3A 0.49336(16) 0.12151(8) 0.24926(7) 0.0193(3) Uani d . 1 . .
C C1A 0.0626(2) -0.22051(13) 0.66575(10) 0.0177(3) Uani d . 1 . .
H H1AA 0.0344 -0.1623 0.7027 0.021 Uiso calc R 1 . .
C C2A 0.0299(2) -0.31450(13) 0.68046(10) 0.0181(3) Uani d . 1 . .
C C3A 0.0749(2) -0.40150(13) 0.62610(11) 0.0214(4) Uani d . 1 . .
H H3AA 0.0551 -0.4644 0.6360 0.026 Uiso calc R 1 . .
C C4A 0.1498(2) -0.39383(13) 0.55681(11) 0.0226(4) Uani d . 1 . .
H H4AA 0.1800 -0.4521 0.5204 0.027 Uiso calc R 1 . .
C C5A 0.1801(2) -0.30062(13) 0.54114(11) 0.0204(4) Uani d . 1 . .
H H5AA 0.2286 -0.2967 0.4942 0.025 Uiso calc R 1 . .
C C6A 0.1373(2) -0.21258(12) 0.59617(10) 0.0173(3) Uani d . 1 . .
C C7A 0.1628(2) -0.11143(13) 0.58357(10) 0.0185(3) Uani d . 1 . .
H H7AA 0.1380 -0.0577 0.6257 0.022 Uiso calc R 1 . .
C C8A 0.2170(2) -0.08706(12) 0.51938(11) 0.0177(3) Uani d . 1 . .
H H8AA 0.2481 -0.1376 0.4763 0.021 Uiso calc R 1 . .
C C9A 0.2285(2) 0.01929(12) 0.51567(10) 0.0161(3) Uani d . 1 . .
C C10A 0.2985(2) 0.04561(12) 0.44537(10) 0.0157(3) Uani d . 1 . .
C C11A 0.3666(2) -0.02568(12) 0.38269(10) 0.0170(3) Uani d . 1 . .
H H11A 0.3692 -0.0926 0.3847 0.020 Uiso calc R 1 . .
C C12A 0.4293(2) 0.00219(12) 0.31843(10) 0.0178(3) Uani d . 1 . .
H H12A 0.4733 -0.0459 0.2773 0.021 Uiso calc R 1 . .
C C13A 0.4270(2) 0.10263(12) 0.31485(10) 0.0160(3) Uani d . 1 . .
C C14A 0.3598(2) 0.17511(12) 0.37613(10) 0.0174(3) Uani d . 1 . .
H H14A 0.3576 0.2420 0.3739 0.021 Uiso calc R 1 . .
C C15A 0.2965(2) 0.14575(12) 0.44015(10) 0.0177(3) Uani d . 1 . .
H H15A 0.2513 0.1938 0.4809 0.021 Uiso calc R 1 . .
C C16A 0.5117(2) 0.22438(12) 0.24321(11) 0.0180(3) Uani d . 1 . .
H H16A 0.5771 0.2680 0.2906 0.022 Uiso calc R 1 . .
H H16B 0.3967 0.2500 0.2370 0.022 Uiso calc R 1 . .
C C17A 0.6112(2) 0.21984(12) 0.17017(10) 0.0176(3) Uani d . 1 . .
H H17A 0.5423 0.1760 0.1239 0.021 Uiso calc R 1 . .
H H17B 0.7215 0.1893 0.1765 0.021 Uiso calc R 1 . .
C C18A 0.6523(2) 0.32204(13) 0.15368(11) 0.0205(4) Uani d . 1 . .
H H18A 0.7172 0.3677 0.2003 0.025 Uiso calc R 1 . .
H H18B 0.5429 0.3514 0.1433 0.025 Uiso calc R 1 . .
C C19A 0.7623(2) 0.30938(13) 0.08122(11) 0.0212(4) Uani d . 1 . .
H H19A 0.8531 0.2637 0.0855 0.025 Uiso calc R 1 . .
H H19B 0.6862 0.2780 0.0331 0.025 Uiso calc R 1 . .
C C20A 0.8507(3) 0.40815(13) 0.07228(12) 0.0250(4) Uani d . 1 . .
H H20A 0.9201 0.4423 0.1218 0.030 Uiso calc R 1 . .
H H20B 0.9308 0.3924 0.0302 0.030 Uiso calc R 1 . .
C C21A 0.7195(3) 0.47918(15) 0.05250(15) 0.0370(5) Uani d . 1 . .
H H21A 0.7821 0.5388 0.0463 0.056 Uiso calc R 1 . .
H H21B 0.6432 0.4978 0.0951 0.056 Uiso calc R 1 . .
H H21C 0.6500 0.4459 0.0036 0.056 Uiso calc R 1 . .
O O1B 1.03690(18) 1.26874(10) -0.36389(8) 0.0221(3) Uani d . 1 . .
O O2B 0.92123(17) 0.87058(9) -0.16144(8) 0.0234(3) Uani d . 1 . .
O O3B 0.58649(17) 0.83300(9) 0.15508(7) 0.0211(3) Uani d . 1 . .
C C1B 0.9824(2) 1.17003(12) -0.27030(10) 0.0167(3) Uani d . 1 . .
H H1BA 1.0148 1.1119 -0.3061 0.020 Uiso calc R 1 . .
C C2B 0.9882(2) 1.26135(12) -0.29143(10) 0.0167(3) Uani d . 1 . .
C C3B 0.9418(2) 1.34888(12) -0.23752(11) 0.0183(3) Uani d . 1 . .
H H3BA 0.9450 1.4101 -0.2511 0.022 Uiso calc R 1 . .
C C4B 0.8907(2) 1.34372(13) -0.16302(11) 0.0192(4) Uani d . 1 . .
H H4BA 0.8612 1.4022 -0.1268 0.023 Uiso calc R 1 . .
C C5B 0.8830(2) 1.25322(13) -0.14194(10) 0.0182(3) Uani d . 1 . .
H H5BA 0.8477 1.2511 -0.0921 0.022 Uiso calc R 1 . .
C C6B 0.9286(2) 1.16495(12) -0.19592(10) 0.0164(3) Uani d . 1 . .
C C7B 0.9226(2) 1.06597(12) -0.17862(10) 0.0182(3) Uani d . 1 . .
H H7BA 0.9728 1.0146 -0.2148 0.022 Uiso calc R 1 . .
C C8B 0.8539(2) 1.04076(12) -0.11739(10) 0.0175(3) Uani d . 1 . .
H H8BA 0.8028 1.0893 -0.0792 0.021 Uiso calc R 1 . .
C C9B 0.8582(2) 0.93598(12) -0.10954(10) 0.0165(3) Uani d . 1 . .
C C10B 0.7870(2) 0.90971(12) -0.03963(10) 0.0156(3) Uani d . 1 . .
C C11B 0.7199(2) 0.98105(12) 0.02337(11) 0.0176(3) Uani d . 1 . .
H H11B 0.7202 1.0483 0.0221 0.021 Uiso calc R 1 . .
C C12B 0.6538(2) 0.95274(12) 0.08697(11) 0.0184(3) Uani d . 1 . .
H H12B 0.6102 1.0008 0.1282 0.022 Uiso calc R 1 . .
C C13B 0.6525(2) 0.85191(12) 0.08946(10) 0.0168(3) Uani d . 1 . .
C C14B 0.7172(2) 0.77927(12) 0.02725(10) 0.0169(3) Uani d . 1 . .
H H14B 0.7155 0.7119 0.0284 0.020 Uiso calc R 1 . .
C C15B 0.7835(2) 0.80879(12) -0.03580(10) 0.0170(3) Uani d . 1 . .
H H15B 0.8270 0.7605 -0.0769 0.020 Uiso calc R 1 . .
C C16B 0.5958(2) 0.73389(12) 0.16826(10) 0.0171(3) Uani d . 1 . .
H H16C 0.7150 0.7123 0.1638 0.020 Uiso calc R 1 . .
H H16D 0.5163 0.6847 0.1294 0.020 Uiso calc R 1 . .
C C17B 0.5415(2) 0.74426(12) 0.25178(10) 0.0169(3) Uani d . 1 . .
H H17C 0.4226 0.7665 0.2545 0.020 Uiso calc R 1 . .
H H17D 0.6192 0.7965 0.2888 0.020 Uiso calc R 1 . .
C C18B 0.5463(2) 0.64715(12) 0.27882(10) 0.0178(3) Uani d . 1 . .
H H18C 0.6643 0.6236 0.2758 0.021 Uiso calc R 1 . .
H H18D 0.4655 0.5950 0.2435 0.021 Uiso calc R 1 . .
C C19B 0.4938(2) 0.66626(13) 0.36472(11) 0.0203(4) Uani d . 1 . .
H H19C 0.5558 0.7288 0.3968 0.024 Uiso calc R 1 . .
H H19D 0.3683 0.6756 0.3647 0.024 Uiso calc R 1 . .
C C20B 0.5329(3) 0.58199(14) 0.40434(12) 0.0244(4) Uani d . 1 . .
H H20C 0.6577 0.5709 0.4029 0.029 Uiso calc R 1 . .
H H20D 0.5080 0.6038 0.4601 0.029 Uiso calc R 1 . .
C C21B 0.4270(3) 0.48291(15) 0.36512(14) 0.0372(5) Uani d . 1 . .
H H21D 0.4515 0.4347 0.3950 0.056 Uiso calc R 1 . .
H H21E 0.4590 0.4574 0.3114 0.056 Uiso calc R 1 . .
H H21F 0.3032 0.4937 0.3642 0.056 Uiso calc R 1 . .
H H1OB 1.074(3) 1.212(2) -0.3885(16) 0.045(7) Uiso d . 1 . .
H H1OA -0.063(4) -0.261(2) 0.7782(18) 0.062(9) Uiso 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'
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
C2A O1A H1OA . . 107.6(18) ?
C13A O3A C16A . . 119.39(13) ?
C2A C1A C6A . . 120.84(16) ?
C2A C1A H1AA . . 119.6 ?
C6A C1A H1AA . . 119.6 ?
O1A C2A C3A . . 118.21(15) ?
O1A C2A C1A . . 121.99(15) ?
C3A C2A C1A . . 119.80(16) ?
C2A C3A C4A . . 119.48(16) ?
C2A C3A H3AA . . 120.3 ?
C4A C3A H3AA . . 120.3 ?
C5A C4A C3A . . 121.01(16) ?
C5A C4A H4AA . . 119.5 ?
C3A C4A H4AA . . 119.5 ?
C4A C5A C6A . . 119.79(16) ?
C4A C5A H5AA . . 120.1 ?
C6A C5A H5AA . . 120.1 ?
C1A C6A C5A . . 119.05(15) ?
C1A C6A C7A . . 117.76(15) ?
C5A C6A C7A . . 123.17(16) ?
C8A C7A C6A . . 128.02(16) ?
C8A C7A H7AA . . 116.0 ?
C6A C7A H7AA . . 116.0 ?
C7A C8A C9A . . 120.77(16) ?
C7A C8A H8AA . . 119.6 ?
C9A C8A H8AA . . 119.6 ?
O2A C9A C8A . . 119.90(16) ?
O2A C9A C10A . . 120.17(15) ?
C8A C9A C10A . . 119.93(14) ?
C15A C10A C11A . . 117.86(16) ?
C15A C10A C9A . . 119.11(15) ?
C11A C10A C9A . . 123.03(15) ?
C12A C11A C10A . . 120.96(15) ?
C12A C11A H11A . . 119.5 ?
C10A C11A H11A . . 119.5 ?
C11A C12A C13A . . 120.12(15) ?
C11A C12A H12A . . 119.9 ?
C13A C12A H12A . . 119.9 ?
O3A C13A C12A . . 115.01(14) ?
O3A C13A C14A . . 124.78(15) ?
C12A C13A C14A . . 120.21(16) ?
C15A C14A C13A . . 118.93(15) ?
C15A C14A H14A . . 120.5 ?
C13A C14A H14A . . 120.5 ?
C14A C15A C10A . . 121.91(15) ?
C14A C15A H15A . . 119.0 ?
C10A C15A H15A . . 119.0 ?
O3A C16A C17A . . 105.46(13) ?
O3A C16A H16A . . 110.6 ?
C17A C16A H16A . . 110.6 ?
O3A C16A H16B . . 110.6 ?
C17A C16A H16B . . 110.6 ?
H16A C16A H16B . . 108.8 ?
C16A C17A C18A . . 114.68(14) ?
C16A C17A H17A . . 108.6 ?
C18A C17A H17A . . 108.6 ?
C16A C17A H17B . . 108.6 ?
C18A C17A H17B . . 108.6 ?
H17A C17A H17B . . 107.6 ?
C17A C18A C19A . . 110.30(14) ?
C17A C18A H18A . . 109.6 ?
C19A C18A H18A . . 109.6 ?
C17A C18A H18B . . 109.6 ?
C19A C18A H18B . . 109.6 ?
H18A C18A H18B . . 108.1 ?
C20A C19A C18A . . 114.49(15) ?
C20A C19A H19A . . 108.6 ?
C18A C19A H19A . . 108.6 ?
C20A C19A H19B . . 108.6 ?
C18A C19A H19B . . 108.6 ?
H19A C19A H19B . . 107.6 ?
C21A C20A C19A . . 113.07(16) ?
C21A C20A H20A . . 109.0 ?
C19A C20A H20A . . 109.0 ?
C21A C20A H20B . . 109.0 ?
C19A C20A H20B . . 109.0 ?
H20A C20A H20B . . 107.8 ?
C20A C21A H21A . . 109.5 ?
C20A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
C20A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
C2B O1B H1OB . . 108.3(18) ?
C13B O3B C16B . . 119.73(13) ?
C2B C1B C6B . . 120.76(15) ?
C2B C1B H1BA . . 119.6 ?
C6B C1B H1BA . . 119.6 ?
O1B C2B C3B . . 117.90(15) ?
O1B C2B C1B . . 122.35(15) ?
C3B C2B C1B . . 119.75(15) ?
C4B C3B C2B . . 119.28(15) ?
C4B C3B H3BA . . 120.4 ?
C2B C3B H3BA . . 120.4 ?
C5B C4B C3B . . 121.31(16) ?
C5B C4B H4BA . . 119.3 ?
C3B C4B H4BA . . 119.3 ?
C4B C5B C6B . . 119.71(16) ?
C4B C5B H5BA . . 120.1 ?
C6B C5B H5BA . . 120.1 ?
C1B C6B C5B . . 119.19(15) ?
C1B C6B C7B . . 117.64(15) ?
C5B C6B C7B . . 123.17(15) ?
C8B C7B C6B . . 127.82(16) ?
C8B C7B H7BA . . 116.1 ?
C6B C7B H7BA . . 116.1 ?
C7B C8B C9B . . 120.59(16) ?
C7B C8B H8BA . . 119.7 ?
C9B C8B H8BA . . 119.7 ?
O2B C9B C10B . . 120.05(15) ?
O2B C9B C8B . . 119.86(15) ?
C10B C9B C8B . . 120.09(14) ?
C15B C10B C11B . . 117.80(15) ?
C15B C10B C9B . . 119.00(15) ?
C11B C10B C9B . . 123.19(15) ?
C12B C11B C10B . . 121.04(15) ?
C12B C11B H11B . . 119.5 ?
C10B C11B H11B . . 119.5 ?
C11B C12B C13B . . 119.99(15) ?
C11B C12B H12B . . 120.0 ?
C13B C12B H12B . . 120.0 ?
O3B C13B C12B . . 114.92(14) ?
O3B C13B C14B . . 124.96(15) ?
C12B C13B C14B . . 120.11(16) ?
C15B C14B C13B . . 119.23(15) ?
C15B C14B H14B . . 120.4 ?
C13B C14B H14B . . 120.4 ?
C14B C15B C10B . . 121.81(15) ?
C14B C15B H15B . . 119.1 ?
C10B C15B H15B . . 119.1 ?
O3B C16B C17B . . 105.71(13) ?
O3B C16B H16C . . 110.6 ?
C17B C16B H16C . . 110.6 ?
O3B C16B H16D . . 110.6 ?
C17B C16B H16D . . 110.6 ?
H16C C16B H16D . . 108.7 ?
C16B C17B C18B . . 114.30(14) ?
C16B C17B H17C . . 108.7 ?
C18B C17B H17C . . 108.7 ?
C16B C17B H17D . . 108.7 ?
C18B C17B H17D . . 108.7 ?
H17C C17B H17D . . 107.6 ?
C17B C18B C19B . . 110.22(14) ?
C17B C18B H18C . . 109.6 ?
C19B C18B H18C . . 109.6 ?
C17B C18B H18D . . 109.6 ?
C19B C18B H18D . . 109.6 ?
H18C C18B H18D . . 108.1 ?
C20B C19B C18B . . 114.61(14) ?
C20B C19B H19C . . 108.6 ?
C18B C19B H19C . . 108.6 ?
C20B C19B H19D . . 108.6 ?
C18B C19B H19D . . 108.6 ?
H19C C19B H19D . . 107.6 ?
C21B C20B C19B . . 113.65(16) ?
C21B C20B H20C . . 108.8 ?
C19B C20B H20C . . 108.8 ?
C21B C20B H20D . . 108.8 ?
C19B C20B H20D . . 108.8 ?
H20C C20B H20D . . 107.7 ?
C20B C21B H21D . . 109.5 ?
C20B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
C20B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
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
O1A C2A . 1.369(2) ?
O1A H1OA . 0.92(3) ?
O2A C9A . 1.237(2) ?
O3A C13A . 1.355(2) ?
O3A C16A . 1.4440(19) ?
C1A C2A . 1.393(2) ?
C1A C6A . 1.396(2) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.389(2) ?
C3A C4A . 1.391(3) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.388(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.399(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.467(2) ?
C7A C8A . 1.330(2) ?
C7A H7AA . 0.9300 ?
C8A C9A . 1.477(2) ?
C8A H8AA . 0.9300 ?
C9A C10A . 1.484(2) ?
C10A C15A . 1.403(2) ?
C10A C11A . 1.407(2) ?
C11A C12A . 1.377(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.398(2) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.398(2) ?
C14A C15A . 1.384(2) ?
C14A H14A . 0.9300 ?
C15A H15A . 0.9300 ?
C16A C17A . 1.509(2) ?
C16A H16A . 0.9700 ?
C16A H16B . 0.9700 ?
C17A C18A . 1.525(2) ?
C17A H17A . 0.9700 ?
C17A H17B . 0.9700 ?
C18A C19A . 1.534(2) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A C20A . 1.531(2) ?
C19A H19A . 0.9700 ?
C19A H19B . 0.9700 ?
C20A C21A . 1.517(3) ?
C20A H20A . 0.9700 ?
C20A H20B . 0.9700 ?
C21A H21A . 0.9600 ?
C21A H21B . 0.9600 ?
C21A H21C . 0.9600 ?
O1B C2B . 1.363(2) ?
O1B H1OB . 0.85(3) ?
O2B C9B . 1.235(2) ?
O3B C13B . 1.355(2) ?
O3B C16B . 1.4428(19) ?
C1B C2B . 1.395(2) ?
C1B C6B . 1.399(2) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.394(2) ?
C3B C4B . 1.394(2) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.384(2) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.400(2) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.466(2) ?
C7B C8B . 1.331(2) ?
C7B H7BA . 0.9300 ?
C8B C9B . 1.482(2) ?
C8B H8BA . 0.9300 ?
C9B C10B . 1.481(2) ?
C10B C15B . 1.404(2) ?
C10B C11B . 1.408(2) ?
C11B C12B . 1.379(2) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.396(2) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.400(2) ?
C14B C15B . 1.379(2) ?
C14B H14B . 0.9300 ?
C15B H15B . 0.9300 ?
C16B C17B . 1.508(2) ?
C16B H16C . 0.9700 ?
C16B H16D . 0.9700 ?
C17B C18B . 1.527(2) ?
C17B H17C . 0.9700 ?
C17B H17D . 0.9700 ?
C18B C19B . 1.529(2) ?
C18B H18C . 0.9700 ?
C18B H18D . 0.9700 ?
C19B C20B . 1.526(2) ?
C19B H19C . 0.9700 ?
C19B H19D . 0.9700 ?
C20B C21B . 1.513(3) ?
C20B H20C . 0.9700 ?
C20B H20D . 0.9700 ?
C21B H21D . 0.9600 ?
C21B H21E . 0.9600 ?
C21B H21F . 0.9600 ?
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
O1B H1OB O2A 1_664 0.86(3) 1.92(3) 2.773(2) 171(2) yes
C1B H1BA O2A 1_664 0.93 2.50 3.196(2) 132 yes
O1A H1OA O2B 1_446 0.92(3) 1.85(3) 2.763(2) 175(3) yes
C1A H1AA O2B 1_446 0.93 2.50 3.214(2) 133 yes
C12B H12B O3A 1_565 0.93 2.56 3.483(2) 175 yes
C12A H12A O3B 1_545 0.93 2.56 3.487(2) 174 yes
C16A H16A Cg1 2_656 0.97 2.80 3.653(2) 147 yes
C16B H16C Cg3 2_775 0.97 2.73 3.595(2) 149 yes
C17B H17C Cg3 2_675 0.97 2.74 3.640(2) 154 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A O1A . . . . -179.04(15) ?
C6A C1A C2A C3A . . . . 1.2(3) ?
O1A C2A C3A C4A . . . . 179.22(15) ?
C1A C2A C3A C4A . . . . -1.0(3) ?
C2A C3A C4A C5A . . . . -0.1(3) ?
C3A C4A C5A C6A . . . . 1.0(3) ?
C2A C1A C6A C5A . . . . -0.3(2) ?
C2A C1A C6A C7A . . . . 178.12(15) ?
C4A C5A C6A C1A . . . . -0.8(3) ?
C4A C5A C6A C7A . . . . -179.09(16) ?
C1A C6A C7A C8A . . . . -173.88(17) ?
C5A C6A C7A C8A . . . . 4.5(3) ?
C6A C7A C8A C9A . . . . 177.51(16) ?
C7A C8A C9A O2A . . . . -3.7(2) ?
C7A C8A C9A C10A . . . . 176.67(15) ?
O2A C9A C10A C15A . . . . -4.2(2) ?
C8A C9A C10A C15A . . . . 175.42(14) ?
O2A C9A C10A C11A . . . . 176.26(16) ?
C8A C9A C10A C11A . . . . -4.1(2) ?
C15A C10A C11A C12A . . . . 0.1(2) ?
C9A C10A C11A C12A . . . . 179.65(15) ?
C10A C11A C12A C13A . . . . 0.3(2) ?
C16A O3A C13A C12A . . . . -174.49(14) ?
C16A O3A C13A C14A . . . . 5.5(2) ?
C11A C12A C13A O3A . . . . 179.47(14) ?
C11A C12A C13A C14A . . . . -0.5(2) ?
O3A C13A C14A C15A . . . . -179.74(15) ?
C12A C13A C14A C15A . . . . 0.2(2) ?
C13A C14A C15A C10A . . . . 0.2(2) ?
C11A C10A C15A C14A . . . . -0.4(2) ?
C9A C10A C15A C14A . . . . -179.95(15) ?
C13A O3A C16A C17A . . . . 172.30(13) ?
O3A C16A C17A C18A . . . . -177.78(14) ?
C16A C17A C18A C19A . . . . 176.80(15) ?
C17A C18A C19A C20A . . . . -165.05(15) ?
C18A C19A C20A C21A . . . . -67.1(2) ?
C6B C1B C2B O1B . . . . -178.82(15) ?
C6B C1B C2B C3B . . . . 0.8(2) ?
O1B C2B C3B C4B . . . . 179.76(15) ?
C1B C2B C3B C4B . . . . 0.1(2) ?
C2B C3B C4B C5B . . . . -0.8(3) ?
C3B C4B C5B C6B . . . . 0.5(3) ?
C2B C1B C6B C5B . . . . -1.1(2) ?
C2B C1B C6B C7B . . . . 178.81(15) ?
C4B C5B C6B C1B . . . . 0.4(2) ?
C4B C5B C6B C7B . . . . -179.44(16) ?
C1B C6B C7B C8B . . . . -170.15(17) ?
C5B C6B C7B C8B . . . . 9.7(3) ?
C6B C7B C8B C9B . . . . 179.51(16) ?
C7B C8B C9B O2B . . . . -2.2(3) ?
C7B C8B C9B C10B . . . . 177.85(15) ?
O2B C9B C10B C15B . . . . -3.5(2) ?
C8B C9B C10B C15B . . . . 176.44(15) ?
O2B C9B C10B C11B . . . . 177.33(16) ?
C8B C9B C10B C11B . . . . -2.7(2) ?
C15B C10B C11B C12B . . . . 0.4(2) ?
C9B C10B C11B C12B . . . . 179.52(15) ?
C10B C11B C12B C13B . . . . -0.1(3) ?
C16B O3B C13B C12B . . . . -173.44(14) ?
C16B O3B C13B C14B . . . . 6.2(2) ?
C11B C12B C13B O3B . . . . 179.27(15) ?
C11B C12B C13B C14B . . . . -0.4(3) ?
O3B C13B C14B C15B . . . . -179.00(15) ?
C12B C13B C14B C15B . . . . 0.6(2) ?
C13B C14B C15B C10B . . . . -0.3(2) ?
C11B C10B C15B C14B . . . . -0.1(2) ?
C9B C10B C15B C14B . . . . -179.32(15) ?
C13B O3B C16B C17B . . . . 170.35(14) ?
O3B C16B C17B C18B . . . . -178.70(13) ?
C16B C17B C18B C19B . . . . 178.55(14) ?
C17B C18B C19B C20B . . . . -167.08(15) ?
C18B C19B C20B C21B . . . . -64.9(2) ?
