##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
# 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          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2009-03-30
_journal_date_accepted     2009-04-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o1033
_journal_page_last     o1033
_journal_paper_category     QO
_journal_coeditor_code     IS2404
_publ_contact_author_name     'V.Manivannan'
_publ_contact_author_address
;
Department of Research and Development,
PRIST University,
Vallam,
Thanjavur - 613 403,
Tamil Nadu,
India.
;
_publ_contact_author_email     'manivan_1999@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '04426187785'
_publ_section_title
;\
Methyl
1-methyl-3-phenyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-\
b]pyrrole-3a-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'B. Gunasekaran'
;
Department of Physics,
AMET University,
Kanathur, Chennai 603 112,
India
;
    'S. Kathiravan'
;
Department of Organic Chemistry,
University of Madras,
Guindy Campus,
Chennai 600 025,
India
;
    'R. Raghunathan'
;
Department of Organic Chemistry,
University of Madras,
Guindy campus,
Chennai 600 025,
India
;
    'V. Renuga'
;
Department of Chemistry,
National College,
Thiruchirapalli,
Tamil Nadu,
India
;
    'V. Manivannan'
;
Department of Research and Development,
PRIST University,
Vallam,
Thanjavur 613 403,
Tamil Nadu,
India
;
_publ_section_synopsis     .
data_I
_chemical_name_systematic
;
Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-
hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H23 N O3'
_chemical_formula_sum     'C24 H23 N O3'
_chemical_formula_iupac     'C24 H23 N O3'
_chemical_formula_weight     373.43
_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     13.2332(6)
_cell_length_b     10.3574(4)
_cell_length_c     15.0865(6)
_cell_angle_alpha     90.00
_cell_angle_beta     111.530(2)
_cell_angle_gamma     90.00
_cell_volume     1923.50(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3865
_cell_measurement_theta_min     1.76
_cell_measurement_theta_max     25.32
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.290
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9793
_exptl_absorpt_correction_T_max     0.9873
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 Kappa APEX2 CCD'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     0
_diffrn_reflns_number     19089
_diffrn_reflns_av_R_equivalents     0.0410
_diffrn_reflns_av_sigmaI/netI     0.0305
_diffrn_reflns_theta_min     2.44
_diffrn_reflns_theta_max     25.32
_diffrn_reflns_theta_full     25.32
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3499
_reflns_number_gt     2413
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0691
_refine_ls_R_factor_gt     0.0399
_refine_ls_wR_factor_gt     0.0921
_refine_ls_wR_factor_ref     0.1073
_refine_ls_goodness_of_fit_ref     1.017
_refine_ls_restrained_S_all     1.017
_refine_ls_number_reflns     3499
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0458P)²+0.3587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.143
_refine_diff_density_min     -0.144
_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, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.87620(10) 0.79656(11) 0.16896(8) 0.0560(3) Uani d . 1 . .
    O O3 0.64358(10) 1.04425(13) 0.12731(9) 0.0610(4) Uani d . 1 . .
    C C8 0.80155(13) 0.91239(15) 0.02018(11) 0.0404(4) Uani d . 1 . .
    O O2 0.72839(11) 0.94550(14) 0.26458(9) 0.0684(4) Uani d . 1 . .
    C C7 0.83173(14) 0.80090(16) 0.07191(12) 0.0473(4) Uani d . 1 . .
    N N1 0.91939(11) 1.10692(13) 0.08087(9) 0.0452(4) Uani d . 1 . .
    C C13 0.81799(13) 1.03987(15) 0.07102(10) 0.0388(4) Uani d . 1 . .
    H H13 0.7558 1.0965 0.0393 0.047 Uiso calc R 1 . .
    C C9 0.74815(13) 0.90220(16) -0.08105(12) 0.0452(4) Uani d . 1 . .
    C C11 0.91380(14) 0.91616(15) 0.21733(12) 0.0483(4) Uani d . 1 . .
    H H11A 0.9827 0.9387 0.2124 0.058 Uiso calc R 1 . .
    H H11B 0.9258 0.9059 0.2843 0.058 Uiso calc R 1 . .
    C C10 0.70597(14) 1.00976(19) -0.14052(12) 0.0508(4) Uani d . 1 . .
    H H10 0.7133 1.0915 -0.1134 0.061 Uiso calc R 1 . .
    C C4 0.73409(15) 0.77937(18) -0.12524(13) 0.0553(5) Uani d . 1 . .
    C C12 0.83340(13) 1.02418(15) 0.17618(10) 0.0394(4) Uani d . 1 . .
    C C23 0.73092(14) 0.99806(16) 0.19506(11) 0.0439(4) Uani d . 1 . .
    C C6 0.81600(17) 0.67864(17) 0.02815(15) 0.0605(5) Uani d . 1 . .
    H H6 0.8373 0.6044 0.0650 0.073 Uiso calc R 1 . .
    C C17 0.95781(14) 1.15779(15) 0.32102(11) 0.0440(4) Uani d . 1 . .
    C C15 0.88052(14) 1.15911(15) 0.21892(11) 0.0448(4) Uani d . 1 . .
    H H15 0.8187 1.2134 0.2160 0.054 Uiso calc R 1 . .
    C C5 0.76969(17) 0.66982(19) -0.06782(15) 0.0665(6) Uani d . 1 . .
    H H5 0.7613 0.5889 -0.0964 0.080 Uiso calc R 1 . .
    C C16 0.93000(15) 1.15213(18) -0.00619(12) 0.0555(5) Uani d . 1 . .
    H H16A 0.8733 1.2130 -0.0371 0.083 Uiso calc R 1 . .
    H H16B 0.9244 1.0802 -0.0479 0.083 Uiso calc R 1 . .
    H H16C 0.9993 1.1931 0.0087 0.083 Uiso calc R 1 . .
    C C3 0.68054(18) 0.7705(2) -0.22541(15) 0.0715(6) Uani d . 1 . .
    H H3 0.6717 0.6900 -0.2546 0.086 Uiso calc R 1 . .
    C C22 1.06811(15) 1.14119(17) 0.34720(13) 0.0580(5) Uani d . 1 . .
    H H22 1.0977 1.1295 0.3006 0.070 Uiso calc R 1 . .
    C C1 0.65478(16) 0.9971(2) -0.23651(13) 0.0629(5) Uani d . 1 . .
    H H1 0.6280 1.0699 -0.2738 0.076 Uiso calc R 1 . .
    C C2 0.64222(18) 0.8763(3) -0.27927(15) 0.0753(6) Uani d . 1 . .
    H H2 0.6075 0.8685 -0.3449 0.090 Uiso calc R 1 . .
    C C14 0.92485(17) 1.21276(17) 0.14582(12) 0.0580(5) Uani d . 1 . .
    H H14A 0.8811 1.2850 0.1117 0.070 Uiso calc R 1 . .
    H H14B 0.9992 1.2417 0.1771 0.070 Uiso calc R 1 . .
    C C18 0.91714(17) 1.17418(17) 0.39259(12) 0.0571(5) Uani d . 1 . .
    H H18 0.8428 1.1855 0.3765 0.069 Uiso calc R 1 . .
    C C19 0.9842(2) 1.1741(2) 0.48683(14) 0.0760(7) Uani d . 1 . .
    H H19 0.9550 1.1846 0.5338 0.091 Uiso calc R 1 . .
    C C21 1.13528(18) 1.14174(19) 0.44215(15) 0.0725(6) Uani d . 1 . .
    H H21 1.2097 1.1306 0.4588 0.087 Uiso calc R 1 . .
    C C20 1.0936(2) 1.1585(2) 0.51178(15) 0.0784(7) Uani d . 1 . .
    H H20 1.1392 1.1594 0.5756 0.094 Uiso calc R 1 . .
    C C24 0.54215(16) 1.0313(2) 0.14187(16) 0.0749(6) Uani d . 1 . .
    H H24A 0.5298 0.9421 0.1518 0.112 Uiso calc R 1 . .
    H H24B 0.4839 1.0628 0.0868 0.112 Uiso calc R 1 . .
    H H24C 0.5453 1.0806 0.1967 0.112 Uiso calc R 1 . .
_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 C7 . 1.3637(19) ?
    O1 C11 . 1.4311(19) ?
    O3 C23 . 1.320(2) ?
    O3 C24 . 1.444(2) ?
    C8 C7 . 1.369(2) ?
    C8 C9 . 1.432(2) ?
    C8 C13 . 1.502(2) ?
    O2 C23 . 1.1931(18) ?
    C7 C6 . 1.408(2) ?
    N1 C16 . 1.449(2) ?
    N1 C14 . 1.454(2) ?
    N1 C13 . 1.469(2) ?
    C13 C12 . 1.532(2) ?
    C13 H13 . 0.9800 ?
    C9 C10 . 1.411(2) ?
    C9 C4 . 1.417(2) ?
    C11 C12 . 1.511(2) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C10 C1 . 1.361(2) ?
    C10 H10 . 0.9300 ?
    C4 C5 . 1.400(3) ?
    C4 C3 . 1.417(3) ?
    C12 C23 . 1.509(2) ?
    C12 C15 . 1.569(2) ?
    C6 C5 . 1.352(3) ?
    C6 H6 . 0.9300 ?
    C17 C22 . 1.376(2) ?
    C17 C18 . 1.382(2) ?
    C17 C15 . 1.504(2) ?
    C15 C14 . 1.531(2) ?
    C15 H15 . 0.9800 ?
    C5 H5 . 0.9300 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C3 C2 . 1.347(3) ?
    C3 H3 . 0.9300 ?
    C22 C21 . 1.381(3) ?
    C22 H22 . 0.9300 ?
    C1 C2 . 1.389(3) ?
    C1 H1 . 0.9300 ?
    C2 H2 . 0.9300 ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C18 C19 . 1.372(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.364(3) ?
    C19 H19 . 0.9300 ?
    C21 C20 . 1.365(3) ?
    C21 H21 . 0.9300 ?
    C20 H20 . 0.9300 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
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
    C7 O1 C11 . . 116.82(12) ?
    C23 O3 C24 . . 116.58(14) ?
    C7 C8 C9 . . 118.20(15) ?
    C7 C8 C13 . . 119.55(14) ?
    C9 C8 C13 . . 122.11(14) ?
    O1 C7 C8 . . 124.11(15) ?
    O1 C7 C6 . . 113.89(16) ?
    C8 C7 C6 . . 121.97(16) ?
    C16 N1 C14 . . 111.70(13) ?
    C16 N1 C13 . . 116.73(13) ?
    C14 N1 C13 . . 104.01(13) ?
    N1 C13 C8 . . 115.02(13) ?
    N1 C13 C12 . . 100.13(12) ?
    C8 C13 C12 . . 112.01(13) ?
    N1 C13 H13 . . 109.8 ?
    C8 C13 H13 . . 109.8 ?
    C12 C13 H13 . . 109.8 ?
    C10 C9 C4 . . 117.20(15) ?
    C10 C9 C8 . . 123.04(15) ?
    C4 C9 C8 . . 119.75(16) ?
    O1 C11 C12 . . 111.76(13) ?
    O1 C11 H11A . . 109.3 ?
    C12 C11 H11A . . 109.3 ?
    O1 C11 H11B . . 109.3 ?
    C12 C11 H11B . . 109.3 ?
    H11A C11 H11B . . 107.9 ?
    C1 C10 C9 . . 121.78(18) ?
    C1 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C5 C4 C9 . . 118.71(17) ?
    C5 C4 C3 . . 122.04(19) ?
    C9 C4 C3 . . 119.19(19) ?
    C23 C12 C11 . . 109.62(13) ?
    C23 C12 C13 . . 115.29(13) ?
    C11 C12 C13 . . 108.05(13) ?
    C23 C12 C15 . . 109.34(13) ?
    C11 C12 C15 . . 112.14(13) ?
    C13 C12 C15 . . 102.29(12) ?
    O2 C23 O3 . . 123.16(16) ?
    O2 C23 C12 . . 124.39(16) ?
    O3 C23 C12 . . 112.40(13) ?
    C5 C6 C7 . . 119.59(18) ?
    C5 C6 H6 . . 120.2 ?
    C7 C6 H6 . . 120.2 ?
    C22 C17 C18 . . 117.86(16) ?
    C22 C17 C15 . . 123.11(16) ?
    C18 C17 C15 . . 119.03(16) ?
    C17 C15 C14 . . 116.40(15) ?
    C17 C15 C12 . . 115.53(13) ?
    C14 C15 C12 . . 103.10(12) ?
    C17 C15 H15 . . 107.1 ?
    C14 C15 H15 . . 107.1 ?
    C12 C15 H15 . . 107.1 ?
    C6 C5 C4 . . 121.67(17) ?
    C6 C5 H5 . . 119.2 ?
    C4 C5 H5 . . 119.2 ?
    N1 C16 H16A . . 109.5 ?
    N1 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    N1 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C2 C3 C4 . . 121.4(2) ?
    C2 C3 H3 . . 119.3 ?
    C4 C3 H3 . . 119.3 ?
    C17 C22 C21 . . 120.56(19) ?
    C17 C22 H22 . . 119.7 ?
    C21 C22 H22 . . 119.7 ?
    C10 C1 C2 . . 120.6(2) ?
    C10 C1 H1 . . 119.7 ?
    C2 C1 H1 . . 119.7 ?
    C3 C2 C1 . . 119.85(19) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    N1 C14 C15 . . 105.93(13) ?
    N1 C14 H14A . . 110.6 ?
    C15 C14 H14A . . 110.6 ?
    N1 C14 H14B . . 110.6 ?
    C15 C14 H14B . . 110.6 ?
    H14A C14 H14B . . 108.7 ?
    C19 C18 C17 . . 121.3(2) ?
    C19 C18 H18 . . 119.3 ?
    C17 C18 H18 . . 119.3 ?
    C20 C19 C18 . . 120.2(2) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C20 C21 C22 . . 120.7(2) ?
    C20 C21 H21 . . 119.7 ?
    C22 C21 H21 . . 119.7 ?
    C19 C20 C21 . . 119.35(19) ?
    C19 C20 H20 . . 120.3 ?
    C21 C20 H20 . . 120.3 ?
    O3 C24 H24A . . 109.5 ?
    O3 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O3 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
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
    C11 O1 C7 C8 . . . . -13.5(2) ?
    C11 O1 C7 C6 . . . . 168.25(15) ?
    C9 C8 C7 O1 . . . . -175.27(14) ?
    C13 C8 C7 O1 . . . . 0.5(2) ?
    C9 C8 C7 C6 . . . . 2.8(2) ?
    C13 C8 C7 C6 . . . . 178.56(16) ?
    C16 N1 C13 C8 . . . . 66.33(19) ?
    C14 N1 C13 C8 . . . . -170.14(13) ?
    C16 N1 C13 C12 . . . . -173.44(13) ?
    C14 N1 C13 C12 . . . . -49.91(15) ?
    C7 C8 C13 N1 . . . . 94.95(17) ?
    C9 C8 C13 N1 . . . . -89.46(18) ?
    C7 C8 C13 C12 . . . . -18.5(2) ?
    C9 C8 C13 C12 . . . . 157.09(14) ?
    C7 C8 C9 C10 . . . . 174.89(15) ?
    C13 C8 C9 C10 . . . . -0.8(2) ?
    C7 C8 C9 C4 . . . . -3.9(2) ?
    C13 C8 C9 C4 . . . . -179.52(14) ?
    C7 O1 C11 C12 . . . . 44.22(19) ?
    C4 C9 C10 C1 . . . . -0.7(2) ?
    C8 C9 C10 C1 . . . . -179.46(15) ?
    C10 C9 C4 C5 . . . . -176.58(16) ?
    C8 C9 C4 C5 . . . . 2.3(2) ?
    C10 C9 C4 C3 . . . . 0.8(2) ?
    C8 C9 C4 C3 . . . . 179.63(15) ?
    O1 C11 C12 C23 . . . . 66.29(17) ?
    O1 C11 C12 C13 . . . . -60.09(17) ?
    O1 C11 C12 C15 . . . . -172.07(13) ?
    N1 C13 C12 C23 . . . . 160.94(13) ?
    C8 C13 C12 C23 . . . . -76.68(17) ?
    N1 C13 C12 C11 . . . . -76.07(15) ?
    C8 C13 C12 C11 . . . . 46.31(17) ?
    N1 C13 C12 C15 . . . . 42.39(15) ?
    C8 C13 C12 C15 . . . . 164.78(13) ?
    C24 O3 C23 O2 . . . . 1.5(3) ?
    C24 O3 C23 C12 . . . . -176.18(15) ?
    C11 C12 C23 O2 . . . . 33.8(2) ?
    C13 C12 C23 O2 . . . . 155.96(16) ?
    C15 C12 C23 O2 . . . . -89.50(19) ?
    C11 C12 C23 O3 . . . . -148.53(14) ?
    C13 C12 C23 O3 . . . . -26.37(19) ?
    C15 C12 C23 O3 . . . . 88.17(16) ?
    O1 C7 C6 C5 . . . . 178.20(16) ?
    C8 C7 C6 C5 . . . . -0.1(3) ?
    C22 C17 C15 C14 . . . . -31.9(2) ?
    C18 C17 C15 C14 . . . . 148.01(16) ?
    C22 C17 C15 C12 . . . . 89.3(2) ?
    C18 C17 C15 C12 . . . . -90.82(19) ?
    C23 C12 C15 C17 . . . . 88.85(17) ?
    C11 C12 C15 C17 . . . . -32.95(19) ?
    C13 C12 C15 C17 . . . . -148.48(14) ?
    C23 C12 C15 C14 . . . . -143.05(14) ?
    C11 C12 C15 C14 . . . . 95.15(16) ?
    C13 C12 C15 C14 . . . . -20.38(16) ?
    C7 C6 C5 C4 . . . . -1.7(3) ?
    C9 C4 C5 C6 . . . . 0.5(3) ?
    C3 C4 C5 C6 . . . . -176.74(18) ?
    C5 C4 C3 C2 . . . . 176.87(19) ?
    C9 C4 C3 C2 . . . . -0.4(3) ?
    C18 C17 C22 C21 . . . . -0.3(3) ?
    C15 C17 C22 C21 . . . . 179.54(17) ?
    C9 C10 C1 C2 . . . . 0.1(3) ?
    C4 C3 C2 C1 . . . . -0.1(3) ?
    C10 C1 C2 C3 . . . . 0.3(3) ?
    C16 N1 C14 C15 . . . . 164.03(14) ?
    C13 N1 C14 C15 . . . . 37.29(17) ?
    C17 C15 C14 N1 . . . . 118.28(16) ?
    C12 C15 C14 N1 . . . . -9.28(17) ?
    C22 C17 C18 C19 . . . . 0.0(3) ?
    C15 C17 C18 C19 . . . . -179.84(17) ?
    C17 C18 C19 C20 . . . . 0.5(3) ?
    C17 C22 C21 C20 . . . . 0.1(3) ?
    C18 C19 C20 C21 . . . . -0.7(3) ?
    C22 C21 C20 C19 . . . . 0.4(3) ?
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
    C11 H11A N1 . 0.97 2.54 2.874(2) 100
    C13 H13 O3 . 0.98 2.39 2.7366(19) 100
    C15 H15 O2 2_655 0.98 2.53 3.347(2) 141
    C16 H16C Cg 3_666 0.96 2.79 3.689(4) 156
