##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-09-28
_journal_date_accepted     2010-10-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     11
_journal_page_first     o2806
_journal_page_last     o2807
_journal_paper_category     QO
_journal_coeditor_code     HB5662
_publ_contact_author_name     'Edward RT Tiekink'
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email     edward.tiekink@gmail.com
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;\
3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(3-nitrophenyl)\
methyl]-5,5-dimethylcyclohex-2-en-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Palakshi Reddy, B.' .
;
Organic Chemistry Division,
School of Advanced Sciences,
VIT University,
Vellore 632 014,
India
;
    'Vijayakumar, V.'
;
Additional correspondence author, e-mail: kvpsvijayakumar@gmail.com.
;
;
Organic Chemistry Division,
School of Advanced Sciences,
VIT University,
Vellore 632 014,
India
;
    'Sarveswari, S.' .
;
Organic Chemistry Division,
School of Advanced Sciences,
VIT University,
Vellore 632 014,
India
;
    'Ng, Seik Weng' .
;
Department of Chemistry,
University of Malaya,
50603 Kuala Lumpur,
Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry,
University of Malaya,
50603 Kuala Lumpur,
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-
en-1-yl)(3-nitrophenyl)methyl]-5,5-dimethylcyclohex-2-en-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H27 N O6'
_chemical_formula_sum     'C23 H27 N O6'
_chemical_formula_iupac     'C23 H27 N O6'
_chemical_formula_weight     413.46
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y+1/2, z+1/2'
    '-x, -y, -z'
    '-x-1/2, y-1/2, -z-1/2'
_cell_length_a     14.2326(10)
_cell_length_b     8.6505(6)
_cell_length_c     16.8410(12)
_cell_angle_alpha     90
_cell_angle_beta     97.7960(10)
_cell_angle_gamma     90
_cell_volume     2054.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5854
_cell_measurement_theta_min     4.5
_cell_measurement_theta_max     28.2
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.337
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     880
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.792
_exptl_absorpt_correction_T_max     0.862
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18883
_diffrn_reflns_av_R_equivalents     0.036
_diffrn_reflns_av_sigmaI/netI     0.033
_diffrn_reflns_theta_min     2.0
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4717
_reflns_number_gt     3928
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.048
_refine_ls_R_factor_gt     0.039
_refine_ls_wR_factor_gt     0.104
_refine_ls_wR_factor_ref     0.112
_refine_ls_goodness_of_fit_ref     1.03
_refine_ls_restrained_S_all     1.03
_refine_ls_number_reflns     4717
_refine_ls_number_parameters     279
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.67P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.37
_refine_diff_density_min     -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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 O1 0.65593(7) 0.65589(10) 0.67564(5) 0.0159(2) Uani d D 1 . .
    H H1o 0.6569(15) 0.594(2) 0.6365(9) 0.048(6) Uiso d D 1 . .
    O O2 0.73862(7) 1.02234(10) 0.49100(5) 0.0170(2) Uani d . 1 . .
    O O3 0.73479(7) 0.82683(11) 0.37346(5) 0.0170(2) Uani d D 1 . .
    H H3o 0.7407(13) 0.8846(19) 0.4154(8) 0.036(5) Uiso d D 1 . .
    O O4 0.63116(6) 0.46796(10) 0.55110(5) 0.0163(2) Uani d . 1 . .
    O O5 0.99653(7) 0.53999(12) 0.35663(6) 0.0237(2) Uani d . 1 . .
    O O6 1.13360(7) 0.63202(12) 0.40630(6) 0.0259(2) Uani d . 1 . .
    N N1 1.04746(8) 0.61823(13) 0.40582(7) 0.0176(2) Uani d . 1 . .
    C C1 0.71426(9) 0.83167(14) 0.58531(7) 0.0129(2) Uani d . 1 . .
    C C2 0.67059(9) 0.79995(14) 0.65085(7) 0.0134(2) Uani d . 1 . .
    C C3 0.63844(9) 0.92120(14) 0.70461(7) 0.0153(3) Uani d . 1 . .
    H H3A 0.6898 0.9405 0.7493 0.018 Uiso calc R 1 . .
    H H3B 0.5829 0.8817 0.7279 0.018 Uiso calc R 1 . .
    C C4 0.61160(9) 1.07463(14) 0.66175(7) 0.0149(3) Uani d . 1 . .
    C C5 0.69030(10) 1.11682(15) 0.61177(8) 0.0184(3) Uani d . 1 . .
    H H5A 0.6701 1.2088 0.5788 0.022 Uiso calc R 1 . .
    H H5B 0.7480 1.1453 0.6486 0.022 Uiso calc R 1 . .
    C C6 0.71497(9) 0.98965(15) 0.55741(8) 0.0145(3) Uani d . 1 . .
    C C7 0.51615(10) 1.05773(17) 0.60799(8) 0.0217(3) Uani d . 1 . .
    H H7A 0.4669 1.0306 0.6409 0.032 Uiso calc R 1 . .
    H H7B 0.5209 0.9761 0.5684 0.032 Uiso calc R 1 . .
    H H7C 0.4997 1.1557 0.5803 0.032 Uiso calc R 1 . .
    C C8 0.60339(10) 1.20199(15) 0.72332(8) 0.0187(3) Uani d . 1 . .
    H H8A 0.5531 1.1754 0.7554 0.028 Uiso calc R 1 . .
    H H8B 0.5880 1.3002 0.6955 0.028 Uiso calc R 1 . .
    H H8C 0.6638 1.2121 0.7585 0.028 Uiso calc R 1 . .
    C C9 0.76179(8) 0.70610(14) 0.54208(7) 0.0124(2) Uani d . 1 . .
    H H9 0.7692 0.6185 0.5812 0.015 Uiso calc R 1 . .
    C C10 0.70261(9) 0.63781(14) 0.46833(7) 0.0129(2) Uani d . 1 . .
    C C11 0.69851(9) 0.69205(14) 0.39210(8) 0.0139(3) Uani d . 1 . .
    C C12 0.65447(9) 0.60340(15) 0.31987(8) 0.0162(3) Uani d . 1 . .
    H H12A 0.6947 0.6153 0.2767 0.019 Uiso calc R 1 . .
    H H12B 0.5916 0.6487 0.3006 0.019 Uiso calc R 1 . .
    C C13 0.64204(9) 0.43071(15) 0.33584(8) 0.0162(3) Uani d . 1 . .
    C C14 0.59406(10) 0.41744(16) 0.41182(8) 0.0189(3) Uani d . 1 . .
    H H14A 0.5281 0.4556 0.3999 0.023 Uiso calc R 1 . .
    H H14B 0.5913 0.3070 0.4268 0.023 Uiso calc R 1 . .
    C C15 0.64394(9) 0.50637(14) 0.48217(7) 0.0140(2) Uani d . 1 . .
    C C16 0.57961(10) 0.35702(17) 0.26472(8) 0.0228(3) Uani d . 1 . .
    H H16A 0.5718 0.2467 0.2752 0.034 Uiso calc R 1 . .
    H H16B 0.6097 0.3698 0.2161 0.034 Uiso calc R 1 . .
    H H16C 0.5174 0.4074 0.2573 0.034 Uiso calc R 1 . .
    C C17 0.73790(10) 0.34775(15) 0.34742(8) 0.0201(3) Uani d . 1 . .
    H H17A 0.7282 0.2378 0.3577 0.030 Uiso calc R 1 . .
    H H17B 0.7786 0.3932 0.3931 0.030 Uiso calc R 1 . .
    H H17C 0.7683 0.3592 0.2989 0.030 Uiso calc R 1 . .
    C C18 0.86411(8) 0.74648(14) 0.53038(7) 0.0130(2) Uani d . 1 . .
    C C19 0.91956(9) 0.84390(15) 0.58406(8) 0.0156(3) Uani d . 1 . .
    H H19 0.8912 0.8949 0.6248 0.019 Uiso calc R 1 . .
    C C20 1.01514(9) 0.86788(15) 0.57927(8) 0.0175(3) Uani d . 1 . .
    H H20 1.0509 0.9350 0.6165 0.021 Uiso calc R 1 . .
    C C21 1.05918(9) 0.79508(15) 0.52075(8) 0.0171(3) Uani d . 1 . .
    H H21 1.1245 0.8105 0.5170 0.021 Uiso calc R 1 . .
    C C22 1.00352(9) 0.69910(15) 0.46819(7) 0.0150(3) Uani d . 1 . .
    C C23 0.90774(9) 0.67322(14) 0.47154(7) 0.0144(3) Uani d . 1 . .
    H H23 0.8724 0.6062 0.4340 0.017 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0196(5) 0.0135(4) 0.0154(4) -0.0009(4) 0.0058(4) 0.0015(3)
    O2 0.0193(5) 0.0155(5) 0.0174(4) -0.0004(4) 0.0067(4) 0.0025(3)
    O3 0.0208(5) 0.0146(4) 0.0161(5) -0.0015(4) 0.0048(4) 0.0019(4)
    O4 0.0186(5) 0.0138(4) 0.0176(4) -0.0009(3) 0.0067(4) 0.0010(3)
    O5 0.0225(5) 0.0281(5) 0.0216(5) 0.0016(4) 0.0070(4) -0.0041(4)
    O6 0.0152(5) 0.0308(6) 0.0342(6) 0.0022(4) 0.0126(4) 0.0012(5)
    N1 0.0169(6) 0.0171(5) 0.0204(6) 0.0040(4) 0.0078(4) 0.0052(4)
    C1 0.0115(6) 0.0124(6) 0.0151(6) 0.0015(4) 0.0027(5) 0.0000(4)
    C2 0.0113(6) 0.0141(6) 0.0146(6) 0.0008(5) 0.0012(4) 0.0017(5)
    C3 0.0167(6) 0.0159(6) 0.0140(6) 0.0006(5) 0.0048(5) -0.0002(5)
    C4 0.0151(6) 0.0155(6) 0.0142(6) 0.0017(5) 0.0029(5) -0.0015(5)
    C5 0.0225(7) 0.0127(6) 0.0216(6) 0.0015(5) 0.0091(5) 0.0001(5)
    C6 0.0113(6) 0.0149(6) 0.0176(6) 0.0000(5) 0.0035(5) 0.0001(5)
    C7 0.0183(7) 0.0257(7) 0.0201(7) 0.0054(5) -0.0003(5) -0.0049(5)
    C8 0.0190(6) 0.0175(6) 0.0198(6) 0.0019(5) 0.0042(5) -0.0034(5)
    C9 0.0123(6) 0.0120(6) 0.0134(6) 0.0007(4) 0.0036(4) 0.0010(4)
    C10 0.0106(5) 0.0126(6) 0.0158(6) 0.0013(5) 0.0029(5) -0.0004(5)
    C11 0.0110(6) 0.0130(6) 0.0183(6) 0.0019(4) 0.0045(5) 0.0010(5)
    C12 0.0159(6) 0.0179(6) 0.0149(6) 0.0005(5) 0.0021(5) 0.0010(5)
    C13 0.0161(6) 0.0173(6) 0.0153(6) -0.0027(5) 0.0028(5) -0.0012(5)
    C14 0.0181(6) 0.0199(7) 0.0194(6) -0.0062(5) 0.0051(5) -0.0017(5)
    C15 0.0120(6) 0.0133(6) 0.0173(6) 0.0029(5) 0.0042(5) 0.0002(5)
    C16 0.0231(7) 0.0258(7) 0.0191(7) -0.0059(6) 0.0012(5) -0.0037(6)
    C17 0.0226(7) 0.0164(6) 0.0214(7) 0.0025(5) 0.0034(5) -0.0026(5)
    C18 0.0118(6) 0.0134(6) 0.0145(6) 0.0019(5) 0.0036(5) 0.0047(4)
    C19 0.0167(6) 0.0157(6) 0.0145(6) 0.0018(5) 0.0028(5) 0.0015(5)
    C20 0.0162(6) 0.0170(6) 0.0185(6) -0.0020(5) -0.0005(5) 0.0020(5)
    C21 0.0131(6) 0.0175(6) 0.0209(6) 0.0007(5) 0.0030(5) 0.0059(5)
    C22 0.0142(6) 0.0145(6) 0.0173(6) 0.0039(5) 0.0058(5) 0.0049(5)
    C23 0.0145(6) 0.0138(6) 0.0152(6) 0.0005(5) 0.0030(5) 0.0023(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    O1 C2 . 1.3395(15) ?
    O1 H1o . 0.851(9) ?
    O2 C6 . 1.2436(15) ?
    O3 C11 . 1.3299(15) ?
    O3 H3o . 0.860(9) ?
    O4 C15 . 1.2443(15) ?
    O5 N1 . 1.2275(15) ?
    O6 N1 . 1.2308(14) ?
    N1 C22 . 1.4704(16) ?
    C1 C2 . 1.3662(17) ?
    C1 C6 . 1.4456(17) ?
    C1 C9 . 1.5169(16) ?
    C2 C3 . 1.4971(17) ?
    C3 C4 . 1.5341(17) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C8 . 1.5282(17) ?
    C4 C5 . 1.5337(18) ?
    C4 C7 . 1.5340(18) ?
    C5 C6 . 1.5029(17) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.5223(17) ?
    C9 C18 . 1.5360(16) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.3607(17) ?
    C10 C15 . 1.4481(17) ?
    C11 C12 . 1.5014(18) ?
    C12 C13 . 1.5323(18) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C17 . 1.5304(18) ?
    C13 C16 . 1.5303(18) ?
    C13 C14 . 1.5343(18) ?
    C14 C15 . 1.5072(18) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 C23 . 1.3913(17) ?
    C18 C19 . 1.3988(18) ?
    C19 C20 . 1.3893(18) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.3886(19) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.3821(19) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.3902(18) ?
    C23 H23 . 0.9500 ?
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
    C2 O1 H1o . . 109.0(14) ?
    C11 O3 H3o . . 108.3(13) ?
    O6 N1 O5 . . 123.66(11) ?
    O6 N1 C22 . . 117.97(11) ?
    O5 N1 C22 . . 118.36(11) ?
    C2 C1 C6 . . 118.45(11) ?
    C2 C1 C9 . . 121.69(11) ?
    C6 C1 C9 . . 119.85(11) ?
    O1 C2 C1 . . 123.08(11) ?
    O1 C2 C3 . . 112.96(10) ?
    C1 C2 C3 . . 123.90(11) ?
    C2 C3 C4 . . 113.50(10) ?
    C2 C3 H3A . . 108.9 ?
    C4 C3 H3A . . 108.9 ?
    C2 C3 H3B . . 108.9 ?
    C4 C3 H3B . . 108.9 ?
    H3A C3 H3B . . 107.7 ?
    C8 C4 C5 . . 109.24(11) ?
    C8 C4 C7 . . 109.03(11) ?
    C5 C4 C7 . . 110.68(11) ?
    C8 C4 C3 . . 109.97(10) ?
    C5 C4 C3 . . 108.08(10) ?
    C7 C4 C3 . . 109.83(11) ?
    C6 C5 C4 . . 114.11(11) ?
    C6 C5 H5A . . 108.7 ?
    C4 C5 H5A . . 108.7 ?
    C6 C5 H5B . . 108.7 ?
    C4 C5 H5B . . 108.7 ?
    H5A C5 H5B . . 107.6 ?
    O2 C6 C1 . . 121.46(12) ?
    O2 C6 C5 . . 119.71(11) ?
    C1 C6 C5 . . 118.79(11) ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C4 C8 H8A . . 109.5 ?
    C4 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C1 C9 C10 . . 115.85(10) ?
    C1 C9 C18 . . 113.02(10) ?
    C10 C9 C18 . . 114.39(10) ?
    C1 C9 H9 . . 103.9 ?
    C10 C9 H9 . . 103.9 ?
    C18 C9 H9 . . 103.9 ?
    C11 C10 C15 . . 118.08(11) ?
    C11 C10 C9 . . 125.74(11) ?
    C15 C10 C9 . . 116.15(10) ?
    O3 C11 C10 . . 123.83(12) ?
    O3 C11 C12 . . 112.91(11) ?
    C10 C11 C12 . . 123.24(11) ?
    C11 C12 C13 . . 113.65(10) ?
    C11 C12 H12A . . 108.8 ?
    C13 C12 H12A . . 108.8 ?
    C11 C12 H12B . . 108.8 ?
    C13 C12 H12B . . 108.8 ?
    H12A C12 H12B . . 107.7 ?
    C17 C13 C16 . . 108.50(11) ?
    C17 C13 C12 . . 110.94(11) ?
    C16 C13 C12 . . 109.71(11) ?
    C17 C13 C14 . . 110.40(11) ?
    C16 C13 C14 . . 110.16(11) ?
    C12 C13 C14 . . 107.12(11) ?
    C15 C14 C13 . . 113.70(11) ?
    C15 C14 H14A . . 108.8 ?
    C13 C14 H14A . . 108.8 ?
    C15 C14 H14B . . 108.8 ?
    C13 C14 H14B . . 108.8 ?
    H14A C14 H14B . . 107.7 ?
    O4 C15 C10 . . 121.35(12) ?
    O4 C15 C14 . . 118.96(11) ?
    C10 C15 C14 . . 119.65(11) ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C13 C17 H17A . . 109.5 ?
    C13 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C13 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C23 C18 C19 . . 117.87(11) ?
    C23 C18 C9 . . 120.68(11) ?
    C19 C18 C9 . . 121.04(11) ?
    C20 C19 C18 . . 121.57(12) ?
    C20 C19 H19 . . 119.2 ?
    C18 C19 H19 . . 119.2 ?
    C19 C20 C21 . . 120.88(12) ?
    C19 C20 H20 . . 119.6 ?
    C21 C20 H20 . . 119.6 ?
    C22 C21 C20 . . 116.90(12) ?
    C22 C21 H21 . . 121.6 ?
    C20 C21 H21 . . 121.6 ?
    C21 C22 C23 . . 123.42(12) ?
    C21 C22 N1 . . 118.75(11) ?
    C23 C22 N1 . . 117.83(11) ?
    C22 C23 C18 . . 119.37(12) ?
    C22 C23 H23 . . 120.3 ?
    C18 C23 H23 . . 120.3 ?
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
    C6 C1 C2 O1 . . . . 171.69(11) ?
    C9 C1 C2 O1 . . . . -8.61(19) ?
    C6 C1 C2 C3 . . . . -11.38(18) ?
    C9 C1 C2 C3 . . . . 168.32(11) ?
    O1 C2 C3 C4 . . . . -153.63(11) ?
    C1 C2 C3 C4 . . . . 29.16(17) ?
    C2 C3 C4 C8 . . . . -166.16(11) ?
    C2 C3 C4 C5 . . . . -46.99(14) ?
    C2 C3 C4 C7 . . . . 73.84(14) ?
    C8 C4 C5 C6 . . . . 171.38(11) ?
    C7 C4 C5 C6 . . . . -68.56(14) ?
    C3 C4 C5 C6 . . . . 51.74(14) ?
    C2 C1 C6 O2 . . . . -167.47(12) ?
    C9 C1 C6 O2 . . . . 12.83(18) ?
    C2 C1 C6 C5 . . . . 15.06(18) ?
    C9 C1 C6 C5 . . . . -164.65(11) ?
    C4 C5 C6 O2 . . . . 145.36(12) ?
    C4 C5 C6 C1 . . . . -37.13(16) ?
    C2 C1 C9 C10 . . . . 96.76(14) ?
    C6 C1 C9 C10 . . . . -83.54(14) ?
    C2 C1 C9 C18 . . . . -128.46(12) ?
    C6 C1 C9 C18 . . . . 51.23(15) ?
    C1 C9 C10 C11 . . . . 88.93(15) ?
    C18 C9 C10 C11 . . . . -45.23(16) ?
    C1 C9 C10 C15 . . . . -89.18(13) ?
    C18 C9 C10 C15 . . . . 136.66(11) ?
    C15 C10 C11 O3 . . . . 167.35(11) ?
    C9 C10 C11 O3 . . . . -10.7(2) ?
    C15 C10 C11 C12 . . . . -14.28(18) ?
    C9 C10 C11 C12 . . . . 167.64(11) ?
    O3 C11 C12 C13 . . . . 160.99(11) ?
    C10 C11 C12 C13 . . . . -17.54(17) ?
    C11 C12 C13 C17 . . . . -71.32(14) ?
    C11 C12 C13 C16 . . . . 168.81(11) ?
    C11 C12 C13 C14 . . . . 49.24(14) ?
    C17 C13 C14 C15 . . . . 68.28(14) ?
    C16 C13 C14 C15 . . . . -171.90(11) ?
    C12 C13 C14 C15 . . . . -52.62(14) ?
    C11 C10 C15 O4 . . . . -167.09(11) ?
    C9 C10 C15 O4 . . . . 11.17(17) ?
    C11 C10 C15 C14 . . . . 10.51(18) ?
    C9 C10 C15 C14 . . . . -171.23(11) ?
    C13 C14 C15 O4 . . . . -157.72(12) ?
    C13 C14 C15 C10 . . . . 24.63(17) ?
    C1 C9 C18 C23 . . . . -159.11(11) ?
    C10 C9 C18 C23 . . . . -23.66(16) ?
    C1 C9 C18 C19 . . . . 28.36(16) ?
    C10 C9 C18 C19 . . . . 163.81(11) ?
    C23 C18 C19 C20 . . . . 0.13(18) ?
    C9 C18 C19 C20 . . . . 172.86(11) ?
    C18 C19 C20 C21 . . . . -0.2(2) ?
    C19 C20 C21 C22 . . . . 0.12(19) ?
    C20 C21 C22 C23 . . . . -0.03(19) ?
    C20 C21 C22 N1 . . . . -179.31(11) ?
    O6 N1 C22 C21 . . . . 4.50(17) ?
    O5 N1 C22 C21 . . . . -176.02(11) ?
    O6 N1 C22 C23 . . . . -174.82(11) ?
    O5 N1 C22 C23 . . . . 4.65(17) ?
    C21 C22 C23 C18 . . . . -0.02(19) ?
    N1 C22 C23 C18 . . . . 179.27(11) ?
    C19 C18 C23 C22 . . . . -0.03(18) ?
    C9 C18 C23 C22 . . . . -172.79(11) ?
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
    O1 H1o O4 . 0.851(9) 1.802(10) 2.6392(13) 167(2)
    O3 H3o O2 . 0.860(9) 1.747(10) 2.5985(13) 170.3(19)
    C5 H5a O4 1_565 0.99 2.34 3.2781(16) 158
    C9 H9 O6 3_766 1.00 2.56 3.3431(16) 135
    C21 H21 O2 3_776 0.95 2.44 3.3121(16) 152