##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.0.1.  #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2000-01-31
_journal_date_accepted     2000-03-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      7
_journal_page_first     827
_journal_page_last     829
_journal_paper_category     FO
_publ_contact_author_name     'Dr Daisuke Hashizume'
_publ_contact_author_address
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 1-5-1 Chofugaoka
 Chofu
 Tokyo 182-8585
 Japan
;
_publ_contact_author_email     'hashi@pc.uec.ac.jp'
_publ_contact_author_fax     '81(424)435501'
_publ_contact_author_phone     '81(424)435495'
_publ_section_title
;
2,3,3a,4,9,9a-Hexahydro-9-phenylbenzo[f]indene derivatives
;
loop_
    _publ_author_name
    _publ_author_address
    'Hashizume, Daisuke'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
    'Takashima, Naoki'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
    'Oikawa, Takashi'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
    'Ishii, Hideki'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
    'Niwa, Haruki'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
    'Iwasaki, Fujiko'
;
 Department of Applied Physics and Chemistry
 The University of Electro-Communications
 Chofugaoka, Chofu, Tokyo 182-8585
 Japan
;
data_I
_chemical_name_systematic
;
3a,9a-trans-9,9a-trans-4,4-dimethyl-9-
phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C21 H24'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     ?
_chemical_formula_weight     276.40
_chemical_melting_point        '373-374'
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.483(2)
_cell_length_b     11.042(2)
_cell_length_c     9.394(2)
_cell_angle_alpha     104.14(2)
_cell_angle_beta     101.45(2)
_cell_angle_gamma     114.03(2)
_cell_volume     820.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     14
_cell_measurement_theta_max     15
_cell_measurement_temperature     298
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .3
_exptl_crystal_size_mid      .3
_exptl_crystal_size_min      .2
_exptl_crystal_density_diffrn     1.119
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     300
_exptl_absorpt_coefficient_mu      .063
_exptl_absorpt_correction_type     \y-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min      .920
_exptl_absorpt_correction_T_max      .987
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'normal-focus rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_method     'ω/2θ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4073
_diffrn_reflns_av_R_equivalents      .019
_diffrn_reflns_av_sigmaI/netI      .024
_diffrn_reflns_theta_min     2.17
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max      .999
_diffrn_measured_fraction_theta_full      .999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%      .387
_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 > 2sigma(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     3769
_reflns_number_gt     2621
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .077
_refine_ls_R_factor_gt      .046
_refine_ls_wR_factor_ref      .149
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     3769
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0726P)²+0.1178P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .176
_refine_diff_density_min      -.212
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SV (Nemoto & Ohashi, 1993)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    C1  .1897(2)  .3213(2)  .75371(19)  .0679 Uani d . 1 . . C
    H11  .2695  .4207  .8109  .102 Uiso calc R 1 . . H
    H12  .2037  .2662  .8161  .102 Uiso calc R 1 . . H
    C2  .0155(3)  .3011(3)  .7131(3)  .0944 Uani d . 1 . . C
    H21  .0134  .3818  .7808  .142 Uiso calc R 1 . . H
    H22  -.0574  .2156  .7260  .142 Uiso calc R 1 . . H
    C3  -.0388(2)  .2886(2)  .5434(2)  .0723 Uani d . 1 . . C
    H31  -.0719  .3596  .5349  .108 Uiso calc R 1 . . H
    H32  -.1301  .1949  .4794  .108 Uiso calc R 1 . . H
    C3a  .11184(17)  .31334(15)  .49179(17)  .0478 Uani d . 1 . . C
    H3a1  .1779  .4165  .5223  .072 Uiso calc R 1 . . H
    C4  .08534(17)  .24763(16)  .31854(17)  .0507 Uani d . 1 . . C
    C4a  .24778(16)  .26046(14)  .30064(15)  .0436 Uani d . 1 . . C
    C5  .2610(2)  .23392(18)  .15135(17)  .0578 Uani d . 1 . . C
    H51  .1718  .2110  .0674  .087 Uiso calc R 1 . . H
    C6  .4004(2)  .24043(19)  .12413(19)  .0624 Uani d . 1 . . C
    H61  .4049  .2218  .0235  .094 Uiso calc R 1 . . H
    C7  .5331(2)  .27476(17)  .24710(19)  .0571 Uani d . 1 . . C
    H71  .6288  .2807  .2304  .086 Uiso calc R 1 . . H
    C8  .52460(17)  .30048(15)  .39561(17)  .0469 Uani d . 1 . . C
    H81  .6154  .3237  .4780  .070 Uiso calc R 1 . . H
    C8a  .38271(16)  .29244(13)  .42545(15)  .0389 Uani d . 1 . . C
    C9  .38332(16)  .32361(13)  .59363(14)  .0397 Uani d . 1 . . C
    H91  .4392  .4273  .6457  .060 Uiso calc R 1 . . H
    C9a  .20861(17)  .26797(15)  .59627(16)  .0453 Uani d . 1 . . C
    H9a1  .1548  .1638  .5578  .068 Uiso calc R 1 . . H
    C10  .47708(16)  .26796(14)  .68466(15)  .0423 Uani d . 1 . . C
    C11  .4323(2)  .12430(16)  .63416(19)  .0581 Uani d . 1 . . C
    H111  .3460  .0619  .5417  .087 Uiso calc R 1 . . H
    C12  .5145(2)  .0727(2)  .7199(2)  .0704 Uani d . 1 . . C
    H121  .4820  -.0240  .6852  .106 Uiso calc R 1 . . H
    C13  .6437(2)  .1636(2)  .8558(2)  .0705 Uani d . 1 . . C
    H131  .6990  .1286  .9129  .106 Uiso calc R 1 . . H
    C14  .6903(2)  .3056(2)  .90650(19)  .0664 Uani d . 1 . . C
    H141  .7781  .3676  .9980  .100 Uiso calc R 1 . . H
    C15  .60727(18)  .35786(17)  .82202(16)  .0532 Uani d . 1 . . C
    H151  .6395  .4546  .8582  .080 Uiso calc R 1 . . H
    C16  .0280(2)  .3308(3)  .2322(2)  .0797 Uani d . 1 . . C
    H161  -.0712  .3253  .2477  .120 Uiso calc R 1 . . H
    H162  .0081  .2902  .1229  .120 Uiso calc R 1 . . H
    H163  .1115  .4286  .2726  .120 Uiso calc R 1 . . H
    C17  -.0438(2)  .0890(2)  .2465(2)  .0845 Uani d . 1 . . C
    H171  -.1486  .0793  .2488  .127 Uiso calc R 1 . . H
    H172  -.0129  .0385  .3053  .127 Uiso calc R 1 . . H
    H173  -.0505  .0505  .1406  .127 Uiso calc R 1 . . H
    CgA  .3916  .2671  .2740 0 Uiso calc . . . . dummy
    CgD  .5609  .2153  .7705 0 Uiso calc . . . . dummy
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1 C9a . 1.527(2) no
    C1 C2 . 1.528(3) no
    C1 H11 .  .9700 no
    C1 H12 .  .9700 no
    C2 C3 . 1.528(3) no
    C2 H21 .  .9700 no
    C2 H22 .  .9700 no
    C3 C3a . 1.540(2) no
    C3 H31 .  .9700 no
    C3 H32 .  .9700 no
    C3a C4 . 1.533(2) no
    C3a C9a . 1.5209(19) no
    C3a H3a1 .  .9800 no
    C4 C4a . 1.5355(19) no
    C4 C17 . 1.539(2) no
    C4 C16 . 1.547(2) no
    C4a C5 . 1.4027(19) no
    C4a C8a . 1.4038(19) no
    C5 C6 . 1.373(2) no
    C5 H51 .  .9300 no
    C6 C7 . 1.372(2) no
    C6 H61 .  .9300 no
    C7 C8 . 1.380(2) no
    C7 H71 .  .9300 no
    C8 C8a . 1.4005(19) no
    C8 H81 .  .9300 no
    C8a C9 . 1.5308(18) no
    C9 C10 . 1.5163(17) no
    C9 C9a . 1.5224(18) no
    C9 H91 .  .9800 no
    C9a H9a1 .  .9800 no
    C10 C15 . 1.385(2) no
    C10 C11 . 1.388(2) no
    C11 C12 . 1.384(2) no
    C11 H111 .  .9300 no
    C12 C13 . 1.375(3) no
    C12 H121 .  .9300 no
    C13 C14 . 1.367(3) no
    C13 H131 .  .9300 no
    C14 C15 . 1.389(2) no
    C14 H141 .  .9300 no
    C15 H151 .  .9300 no
    C16 H161 .  .9600 no
    C16 H162 .  .9600 no
    C16 H163 .  .9600 no
    C17 H171 .  .9600 no
    C17 H172 .  .9600 no
    C17 H173 .  .9600 no
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
    C9a C1 C2 . . 104.58(14) no
    C9a C1 H11 . . 110.8 no
    C2 C1 H11 . . 110.8 no
    C9a C1 H12 . . 110.8 no
    C2 C1 H12 . . 110.8 no
    H11 C1 H12 . . 108.9 no
    C1 C2 C3 . . 107.15(15) no
    C1 C2 H21 . . 110.3 no
    C3 C2 H21 . . 110.3 no
    C1 C2 H22 . . 110.3 no
    C3 C2 H22 . . 110.3 no
    H21 C2 H22 . . 108.5 no
    C2 C3 C3a . . 105.52(14) no
    C2 C3 H31 . . 110.6 no
    C3a C3 H31 . . 110.6 no
    C2 C3 H32 . . 110.6 no
    C3a C3 H32 . . 110.6 no
    H31 C3 H32 . . 108.8 no
    C9a C3a C4 . . 113.35(11) no
    C9a C3a C3 . . 104.16(13) no
    C4 C3a C3 . . 118.91(13) no
    C9a C3a H3a1 . . 106.6 no
    C4 C3a H3a1 . . 106.6 no
    C3 C3a H3a1 . . 106.6 no
    C3a C4 C4a . . 109.07(11) no
    C3a C4 C17 . . 112.22(13) no
    C4a C4 C17 . . 108.11(14) no
    C3a C4 C16 . . 107.89(13) no
    C4a C4 C16 . . 110.20(13) no
    C17 C4 C16 . . 109.36(15) no
    C5 C4a C8a . . 117.87(13) no
    C5 C4a C4 . . 118.68(13) no
    C8a C4a C4 . . 123.40(12) no
    C6 C5 C4a . . 122.64(15) no
    C6 C5 H51 . . 118.7 no
    C4a C5 H51 . . 118.7 no
    C7 C6 C5 . . 119.20(14) no
    C7 C6 H61 . . 120.4 no
    C5 C6 H61 . . 120.4 no
    C6 C7 C8 . . 119.97(14) no
    C6 C7 H71 . . 120.0 no
    C8 C7 H71 . . 120.0 no
    C7 C8 C8a . . 121.69(14) no
    C7 C8 H81 . . 119.2 no
    C8a C8 H81 . . 119.2 no
    C8 C8a C4a . . 118.61(12) no
    C8 C8a C9 . . 118.58(11) no
    C4a C8a C9 . . 122.78(12) no
    C10 C9 C9a . . 111.80(11) no
    C10 C9 C8a . . 113.00(10) no
    C9a C9 C8a . . 110.24(11) no
    C10 C9 H91 . . 107.2 no
    C9a C9 H91 . . 107.2 no
    C8a C9 H91 . . 107.2 no
    C3a C9a C9 . . 110.95(11) no
    C3a C9a C1 . . 103.48(12) no
    C9 C9a C1 . . 116.29(13) no
    C3a C9a H9a1 . . 108.6 no
    C9 C9a H9a1 . . 108.6 no
    C1 C9a H9a1 . . 108.6 no
    C15 C10 C11 . . 118.00(13) no
    C15 C10 C9 . . 121.25(13) no
    C11 C10 C9 . . 120.74(13) no
    C12 C11 C10 . . 120.76(16) no
    C12 C11 H111 . . 119.6 no
    C10 C11 H111 . . 119.6 no
    C13 C12 C11 . . 120.48(17) no
    C13 C12 H121 . . 119.8 no
    C11 C12 H121 . . 119.8 no
    C14 C13 C12 . . 119.48(15) no
    C14 C13 H131 . . 120.3 no
    C12 C13 H131 . . 120.3 no
    C13 C14 C15 . . 120.35(16) no
    C13 C14 H141 . . 119.8 no
    C15 C14 H141 . . 119.8 no
    C10 C15 C14 . . 120.93(16) no
    C10 C15 H151 . . 119.5 no
    C14 C15 H151 . . 119.5 no
    C4 C16 H161 . . 109.5 no
    C4 C16 H162 . . 109.5 no
    H161 C16 H162 . . 109.5 no
    C4 C16 H163 . . 109.5 no
    H161 C16 H163 . . 109.5 no
    H162 C16 H163 . . 109.5 no
    C4 C17 H171 . . 109.5 no
    C4 C17 H172 . . 109.5 no
    H171 C17 H172 . . 109.5 no
    C4 C17 H173 . . 109.5 no
    H171 C17 H173 . . 109.5 no
    H172 C17 H173 . . 109.5 no
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
    C9a C1 C2 C3 . . . . -19.5(2) no
    C1 C2 C3 C3a . . . . -4.2(2) no
    C2 C3 C3a C9a . . . . 26.40(19) no
    C2 C3 C3a C4 . . . . 153.73(16) no
    C9a C3a C4 C4a . . . . -45.62(16) no
    C3 C3a C4 C4a . . . . -168.49(14) no
    C9a C3a C4 C17 . . . . 74.14(17) no
    C3 C3a C4 C17 . . . . -48.7(2) no
    C9a C3a C4 C16 . . . . -165.32(13) no
    C3 C3a C4 C16 . . . . 71.81(18) no
    C3a C4 C4a C5 . . . . -167.22(13) no
    C17 C4 C4a C5 . . . . 70.50(18) no
    C16 C4 C4a C5 . . . . -48.96(19) no
    C3a C4 C4a C8a . . . . 15.20(18) no
    C17 C4 C4a C8a . . . . -107.08(17) no
    C16 C4 C4a C8a . . . . 133.46(15) no
    C8a C4a C5 C6 . . . . -1.1(2) no
    C4 C4a C5 C6 . . . . -178.82(15) no
    C4a C5 C6 C7 . . . .  -.3(3) no
    C5 C6 C7 C8 . . . .  .8(2) no
    C6 C7 C8 C8a . . . .  .1(2) no
    C7 C8 C8a C4a . . . . -1.5(2) no
    C7 C8 C8a C9 . . . . -179.52(12) no
    C5 C4a C8a C8 . . . . 1.92(19) no
    C4 C4a C8a C8 . . . . 179.52(12) no
    C5 C4a C8a C9 . . . . 179.89(12) no
    C4 C4a C8a C9 . . . . -2.5(2) no
    C8 C8a C9 C10 . . . . -37.39(16) no
    C4a C8a C9 C10 . . . . 144.64(12) no
    C8 C8a C9 C9a . . . . -163.31(11) no
    C4a C8a C9 C9a . . . . 18.72(16) no
    C4 C3a C9a C9 . . . . 65.33(15) no
    C3 C3a C9a C9 . . . . -163.98(12) no
    C4 C3a C9a C1 . . . . -169.25(13) no
    C3 C3a C9a C1 . . . . -38.57(16) no
    C10 C9 C9a C3a . . . . -174.55(11) no
    C8a C9 C9a C3a . . . . -47.97(14) no
    C10 C9 C9a C1 . . . . 67.56(16) no
    C8a C9 C9a C1 . . . . -165.85(12) no
    C2 C1 C9a C3a . . . . 35.91(18) no
    C2 C1 C9a C9 . . . . 157.82(15) no
    C9a C9 C10 C15 . . . . -112.21(14) no
    C8a C9 C10 C15 . . . . 122.72(14) no
    C9a C9 C10 C11 . . . . 66.37(17) no
    C8a C9 C10 C11 . . . . -58.71(17) no
    C15 C10 C11 C12 . . . .  .7(2) no
    C9 C10 C11 C12 . . . . -177.90(14) no
    C10 C11 C12 C13 . . . .  -.9(3) no
    C11 C12 C13 C14 . . . .  .3(3) no
    C12 C13 C14 C15 . . . .  .4(3) no
    C11 C10 C15 C14 . . . .  .0(2) no
    C9 C10 C15 C14 . . . . 178.61(13) no
    C13 C14 C15 C10 . . . .  -.6(3) no
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
    C9 H91 C4a 2_666  .98 3.34 4.198(2) 147.0 no
    C9 H91 C5 2_666  .98 3.38 4.317(3) 161.1 no
    C9 H91 C6 2_666  .98 3.27 4.240(3) 168.5 no
    C9 H91 C7 2_666  .98 3.08 3.995(2) 156.2 no
    C9 H91 C8 2_666  .98 3.01 3.848(2) 143.8 yes
    C9 H91 C8a 2_666  .98 3.17 3.975(2) 139.9 no
    C9 H91 CgA 2_666  .98 2.90 3.86 166.2 yes
    C6 H61 C10 1_554  .93 3.50 4.392(2) 162.0 no
    C6 H61 C11 1_554  .93 3.64 4.572(3) 174.8 no
    C6 H61 C12 1_554  .93 3.49 4.341(3) 152.8 no
    C6 H61 C13 1_554  .93 3.18 3.905(3) 136.0 no
    C6 H61 C14 1_554  .93 3.00 3.687(3) 131.4 yes
    C6 H61 C15 1_554  .93 3.16 3.939(2) 142.1 no
    C6 H61 CgD 1_554  .93 3.04 3.91 157.4 yes
data_II
_chemical_name_systematic
;
3a,4-trans-3a,9a-cis-9,9a-trans-4-methoxy-9-
phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C20 H22 O'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     ?
_chemical_formula_weight     278.38
_chemical_melting_point     ?
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.0001(8)
_cell_length_b     19.287(2)
_cell_length_c     8.9918(8)
_cell_angle_alpha     96.654(8)
_cell_angle_beta     101.494(7)
_cell_angle_gamma     97.908(8)
_cell_volume     1498.4(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     14
_cell_measurement_theta_max     15
_cell_measurement_temperature     100
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .30
_exptl_crystal_size_mid      .19
_exptl_crystal_size_min      .12
_exptl_crystal_density_diffrn     1.234
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu      .074
_exptl_absorpt_correction_type     '\y-scan'
_exptl_absorpt_process_details     'North et al., 1968'
_exptl_absorpt_correction_T_min      .965
_exptl_absorpt_correction_T_max      .991
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'normal-focus rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_method     'ω/2θ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12299
_diffrn_reflns_av_R_equivalents      .016
_diffrn_reflns_av_sigmaI/netI      .038
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     3
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%      .729
_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 > 2sigma(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     8747
_reflns_number_gt     6799
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .062
_refine_ls_R_factor_gt      .042
_refine_ls_wR_factor_ref      .121
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     8747
_refine_ls_number_parameters     555
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0585P)²+0.3481P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .432
_refine_diff_density_min      -.262
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_structure_solution     'SIR97 (Altomare et al., 1998)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SV (Nemoto & Ohashi, 1993)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    C1X  .17475(13)  .07985(6)  .89731(12)  .0177 Uani d . 1 . . C
    H11X  .2807(16)  .0761(7)  .9538(16)  .015(3) Uiso d . 1 . . H
    H12X  .0987(17)  .0504(8)  .9395(17)  .024(4) Uiso d . 1 . . H
    C2X  .15187(14)  .15727(6)  .90588(13)  .0196 Uani d . 1 . . C
    H21X  .1950(18)  .1850(8) 1.0097(18)  .028(4) Uiso d . 1 . . H
    H22X  .0413(17)  .1608(7)  .8808(16)  .020(3) Uiso d . 1 . . H
    C3X  .22946(14)  .18390(6)  .78181(13)  .0193 Uani d . 1 . . C
    H31X  .1994(17)  .2301(8)  .7501(17)  .024(4) Uiso d . 1 . . H
    H32X  .3442(17)  .1909(7)  .8174(16)  .020(3) Uiso d . 1 . . H
    C3aX  .18343(12)  .12211(5)  .64901(11)  .01424 Uani d . 1 . . C
    H3a1X  .0816(16)  .1261(7)  .5830(15)  .015(3) Uiso d . 1 . . H
    C4X  .29768(12)  .12076(5)  .54401(12)  .01476 Uani d . 1 . . C
    H41X  .4020(16)  .1307(7)  .6086(15)  .014(3) Uiso d . 1 . . H
    C4aX  .27782(12)  .04863(5)  .44914(12)  .01446 Uani d . 1 . . C
    C5X  .26173(12)  .03805(6)  .29039(12)  .0170 Uani d . 1 . . C
    H51X  .2577(17)  .0791(8)  .2372(17)  .021(3) Uiso d . 1 . . H
    C6X  .25213(13)  -.02969(6)  .21175(12)  .0188 Uani d . 1 . . C
    H61X  .2380(16)  -.0368(8)  .0998(17)  .020(3) Uiso d . 1 . . H
    C7X  .26092(13)  -.08684(6)  .29251(12)  .0188 Uani d . 1 . . C
    H71X  .2566(18)  -.1342(8)  .2366(17)  .025(4) Uiso d . 1 . . H
    C8X  .27185(12)  -.07690(6)  .45070(12)  .01623 Uani d . 1 . . C
    H81X  .2769(17)  -.1180(8)  .5054(17)  .024(4) Uiso d . 1 . . H
    C8aX  .27786(11)  -.00968(5)  .52969(11)  .01377 Uani d . 1 . . C
    C9X  .28187(12)  .00529(5)  .70043(11)  .01334 Uani d . 1 . . C
    H91X  .3874(17)  .0333(7)  .7522(16)  .019(3) Uiso d . 1 . . H
    C9aX  .16330(12)  .05382(5)  .72561(11)  .01406 Uani d . 1 . . C
    H9a1X  .0599(17)  .0264(7)  .6788(17)  .020(3) Uiso d . 1 . . H
    C10X  .25862(12)  -.06166(5)  .77241(11)  .01416 Uani d . 1 . . C
    C11X  .38367(12)  -.08411(6)  .86041(12)  .01648 Uani d . 1 . . C
    H111X  .4874(18)  -.0551(8)  .8767(17)  .025(4) Uiso d . 1 . . H
    C12X  .36443(14)  -.14673(6)  .92318(13)  .0208 Uani d . 1 . . C
    H121X  .4562(19)  -.1619(8)  .9858(18)  .030(4) Uiso d . 1 . . H
    C13X  .22016(14)  -.18770(6)  .89813(13)  .0215 Uani d . 1 . . C
    H131X  .2092(18)  -.2317(8)  .9406(18)  .027(4) Uiso d . 1 . . H
    C14X  .09434(13)  -.16591(6)  .81039(13)  .0204 Uani d . 1 . . C
    H141X  -.0069(18)  -.1935(8)  .7924(17)  .026(4) Uiso d . 1 . . H
    C15X  .11375(13)  -.10325(6)  .74822(12)  .0177 Uani d . 1 . . C
    H151X  .0255(17)  -.0886(8)  .6892(17)  .022(4) Uiso d . 1 . . H
    O1X  .28090(10)  .17657(4)  .45421(9)  .01998 Uani d . 1 . . O
    C16X  .42121(16)  .20589(7)  .41787(16)  .0275 Uani d . 1 . . C
    H161X  .5030(19)  .2249(8)  .5145(19)  .031(4) Uiso d . 1 . . H
    H162X  .3966(19)  .2451(9)  .3624(19)  .033(4) Uiso d . 1 . . H
    H163X  .460(2)  .1708(9)  .352(2)  .038(5) Uiso d . 1 . . H
    CgAX  .2671  -.0194  .3707 0 Uiso calc . . . . dummy
    CgDX  .2392  -.1249  .8355 0 Uiso calc . . . . dummy
    C1Y  .09569(13)  .45094(6)  .26877(15)  .0223 Uani d . 1 . . C
    H11Y  .0479(18)  .4724(8)  .1756(18)  .028(4) Uiso d . 1 . . H
    H12Y  .0476(19)  .4665(9)  .3552(19)  .033(4) Uiso d . 1 . . H
    C2Y  .06822(13)  .37070(6)  .22366(15)  .0230 Uani d . 1 . . C
    H21Y  -.0401(19)  .3507(8)  .1614(18)  .030(4) Uiso d . 1 . . H
    H22Y  .0823(18)  .3470(8)  .3193(18)  .027(4) Uiso d . 1 . . H
    C3Y  .19496(14)  .35885(7)  .13737(15)  .0259 Uani d . 1 . . C
    H31Y  .210(2)  .3089(9)  .1257(19)  .036(4) Uiso d . 1 . . H
    H32Y  .170(2)  .3739(9)  .032(2)  .037(4) Uiso d . 1 . . H
    C3aY  .33807(12)  .40931(6)  .23547(12)  .0172 Uani d . 1 . . C
    H3a1Y  .3876(18)  .3864(8)  .3233(17)  .026(4) Uiso d . 1 . . H
    C4Y  .46475(12)  .43085(6)  .14870(12)  .01668 Uani d . 1 . . C
    H41Y  .4119(16)  .4373(7)  .0397(16)  .018(3) Uiso d . 1 . . H
    C4aY  .56725(12)  .49936(5)  .22675(12)  .01587 Uani d . 1 . . C
    C5Y  .72681(12)  .50830(6)  .24910(13)  .0185 Uani d . 1 . . C
    H51Y  .7749(19)  .4678(9)  .2162(18)  .030(4) Uiso d . 1 . . H
    C6Y  .81655(13)  .57324(6)  .31727(13)  .0202 Uani d . 1 . . C
    H61Y  .9270(19)  .5792(8)  .3311(18)  .030(4) Uiso d . 1 . . H
    C7Y  .74637(13)  .62956(6)  .36203(13)  .0198 Uani d . 1 . . C
    H71Y  .8084(18)  .6766(8)  .4092(18)  .026(4) Uiso d . 1 . . H
    C8Y  .58678(12)  .62097(6)  .33945(12)  .0171 Uani d . 1 . . C
    H81Y  .5373(16)  .6608(7)  .3674(16)  .017(3) Uiso d . 1 . . H
    C8aY  .49613(12)  .55611(5)  .27217(12)  .01517 Uani d . 1 . . C
    C9Y  .32202(12)  .54230(5)  .24341(12)  .01526 Uani d . 1 . . C
    H91Y  .2791(17)  .5327(8)  .1258(17)  .022(3) Uiso d . 1 . . H
    C9aY  .27206(12)  .47359(5)  .30533(12)  .01601 Uani d . 1 . . C
    H9a1Y  .3120(16)  .4811(7)  .4184(16)  .016(3) Uiso d . 1 . . H
    C10Y  .25510(12)  .60448(5)  .30606(13)  .0169 Uani d . 1 . . C
    C11Y  .18400(13)  .64635(6)  .20634(15)  .0225 Uani d . 1 . . C
    H111Y  .1765(18)  .6335(8)  .0975(18)  .027(4) Uiso d . 1 . . H
    C12Y  .12451(15)  .70474(7)  .26193(18)  .0291 Uani d . 1 . . C
    H121Y  .074(2)  .7316(9)  .191(2)  .038(5) Uiso d . 1 . . H
    C13Y  .13645(15)  .72235(6)  .41807(18)  .0306 Uani d . 1 . . C
    H131Y  .094(2)  .7634(9)  .460(2)  .038(5) Uiso d . 1 . . H
    C14Y  .20719(14)  .68123(7)  .51869(16)  .0265 Uani d . 1 . . C
    H141Y  .2187(19)  .6938(9)  .628(2)  .034(4) Uiso d . 1 . . H
    C15Y  .26564(13)  .62262(6)  .46337(14)  .0209 Uani d . 1 . . C
    H151Y  .3185(17)  .5949(8)  .5361(17)  .022(4) Uiso d . 1 . . H
    O1Y  .56203(10)  .37890(4)  .13506(10)  .02288 Uani d . 1 . . O
    C16Y  .49376(15)  .31733(6)  .02903(15)  .0246 Uani d . 1 . . C
    H161Y  .4362(19)  .2808(8)  .0787(18)  .030(4) Uiso d . 1 . . H
    H162Y  .4204(18)  .3285(8)  -.0609(18)  .027(4) Uiso d . 1 . . H
    H163Y  .580(2)  .2982(9)  -.003(2)  .042(5) Uiso d . 1 . . H
    CgAY  .6566  .5646  .2945 0 Uiso calc . . . . dummy
    CgDY  .1955  .6636  .3618 0 Uiso calc . . . . dummy
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1X C2X . 1.5304(15) no
    C1X C9aX . 1.5456(14) no
    C1X H11X . 1.004(14) no
    C1X H12X .  .990(15) no
    C2X C3X . 1.5299(16) no
    C2X H21X .  .996(16) no
    C2X H22X .  .989(15) no
    C3X C3aX . 1.5346(14) no
    C3X H31X . 1.022(15) no
    C3X H32X . 1.003(15) no
    C3aX C4X . 1.5290(14) no
    C3aX C9aX . 1.5609(14) no
    C3aX H3a1X . 1.006(14) no
    C4X O1X . 1.4251(12) no
    C4X C4aX . 1.5136(14) no
    C4X H41X .  .981(14) no
    C4aX C5X . 1.3936(14) no
    C4aX C8aX . 1.4065(14) no
    C5X C6X . 1.3945(15) no
    C5X H51X .  .972(15) no
    C6X C7X . 1.3910(15) no
    C6X H61X .  .980(14) no
    C7X C8X . 1.3949(14) no
    C7X H71X .  .982(15) no
    C8X C8aX . 1.3931(14) no
    C8X H81X .  .981(15) no
    C8aX C9X . 1.5211(14) no
    C9X C10X . 1.5177(14) no
    C9X C9aX . 1.5455(14) no
    C9X H91X . 1.017(15) no
    C9aX H9a1X .  .990(15) no
    C10X C11X . 1.3925(14) no
    C10X C15X . 1.3963(15) no
    C11X C12X . 1.3951(15) no
    C11X H111X .  .994(16) no
    C12X C13X . 1.3860(17) no
    C12X H121X . 1.003(16) no
    C13X C14X . 1.3904(17) no
    C13X H131X .  .971(16) no
    C14X C15X . 1.3932(15) no
    C14X H141X .  .963(16) no
    C15X H151X .  .960(15) no
    O1X C16X . 1.4254(15) no
    C16X H161X . 1.014(17) no
    C16X H162X .  .979(17) no
    C16X H163X .  .992(18) no
    C1Y C2Y . 1.5265(17) no
    C1Y C9aY . 1.5448(15) no
    C1Y H11Y . 1.022(16) no
    C1Y H12Y .  .998(17) no
    C2Y C3Y . 1.5293(17) no
    C2Y H21Y . 1.021(16) no
    C2Y H22Y . 1.014(16) no
    C3Y C3aY . 1.5451(16) no
    C3Y H31Y .  .987(17) no
    C3Y H32Y . 1.010(17) no
    C3aY C4Y . 1.5428(15) no
    C3aY C9aY . 1.5670(15) no
    C3aY H3a1Y . 1.007(15) no
    C4Y O1Y . 1.4287(13) no
    C4Y C4aY . 1.5105(15) no
    C4Y H41Y . 1.029(14) no
    C4aY C5Y . 1.3932(15) no
    C4aY C8aY . 1.4028(14) no
    C5Y C6Y . 1.3942(16) no
    C5Y H51Y .  .989(16) no
    C6Y C7Y . 1.3891(16) no
    C6Y H61Y .  .966(16) no
    C7Y C8Y . 1.3936(15) no
    C7Y H71Y .  .996(16) no
    C8Y C8aY . 1.3942(15) no
    C8Y H81Y .  .972(14) no
    C8aY C9Y . 1.5169(14) no
    C9Y C10Y . 1.5152(14) no
    C9Y C9aY . 1.5413(15) no
    C9Y H91Y . 1.036(15) no
    C9aY H9a1Y .  .995(14) no
    C10Y C11Y . 1.3954(16) no
    C10Y C15Y . 1.3982(16) no
    C11Y C12Y . 1.3954(17) no
    C11Y H111Y .  .968(16) no
    C12Y C13Y . 1.385(2) no
    C12Y H121Y .  .953(18) no
    C13Y C14Y . 1.389(2) no
    C13Y H131Y .  .992(18) no
    C14Y C15Y . 1.3927(16) no
    C14Y H141Y .  .966(17) no
    C15Y H151Y .  .984(15) no
    O1Y C16Y . 1.4142(14) no
    C16Y H161Y . 1.014(16) no
    C16Y H162Y . 1.002(16) no
    C16Y H163Y .  .984(18) no
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
    C2X C1X C9aX . . 105.46(8) no
    C2X C1X H11X . . 110.8(8) no
    C9aX C1X H11X . . 107.3(8) no
    C2X C1X H12X . . 112.8(9) no
    C9aX C1X H12X . . 111.8(9) no
    H11X C1X H12X . . 108.6(11) no
    C3X C2X C1X . . 103.34(9) no
    C3X C2X H21X . . 113.4(9) no
    C1X C2X H21X . . 112.9(9) no
    C3X C2X H22X . . 109.8(8) no
    C1X C2X H22X . . 110.9(8) no
    H21X C2X H22X . . 106.6(12) no
    C2X C3X C3aX . . 103.94(9) no
    C2X C3X H31X . . 113.8(9) no
    C3aX C3X H31X . . 112.8(8) no
    C2X C3X H32X . . 110.2(8) no
    C3aX C3X H32X . . 107.4(8) no
    H31X C3X H32X . . 108.4(12) no
    C4X C3aX C3X . . 113.41(9) no
    C4X C3aX C9aX . . 113.04(8) no
    C3X C3aX C9aX . . 105.60(8) no
    C4X C3aX H3a1X . . 106.7(8) no
    C3X C3aX H3a1X . . 109.4(8) no
    C9aX C3aX H3a1X . . 108.6(8) no
    O1X C4X C4aX . . 113.56(8) no
    O1X C4X C3aX . . 108.15(8) no
    C4aX C4X C3aX . . 111.29(8) no
    O1X C4X H41X . . 107.7(8) no
    C4aX C4X H41X . . 107.8(8) no
    C3aX C4X H41X . . 108.2(8) no
    C5X C4aX C8aX . . 119.82(9) no
    C5X C4aX C4X . . 123.66(9) no
    C8aX C4aX C4X . . 116.52(9) no
    C4aX C5X C6X . . 120.36(10) no
    C4aX C5X H51X . . 118.0(9) no
    C6X C5X H51X . . 121.6(9) no
    C7X C6X C5X . . 119.80(10) no
    C7X C6X H61X . . 120.4(8) no
    C5X C6X H61X . . 119.8(8) no
    C6X C7X C8X . . 120.04(10) no
    C6X C7X H71X . . 119.3(9) no
    C8X C7X H71X . . 120.6(9) no
    C8aX C8X C7X . . 120.51(10) no
    C8aX C8X H81X . . 120.7(9) no
    C7X C8X H81X . . 118.8(9) no
    C8X C8aX C4aX . . 119.32(9) no
    C8X C8aX C9X . . 123.90(9) no
    C4aX C8aX C9X . . 116.77(9) no
    C10X C9X C8aX . . 112.83(8) no
    C10X C9X C9aX . . 112.31(8) no
    C8aX C9X C9aX . . 109.06(8) no
    C10X C9X H91X . . 108.3(8) no
    C8aX C9X H91X . . 107.3(8) no
    C9aX C9X H91X . . 106.8(8) no
    C9X C9aX C1X . . 112.47(8) no
    C9X C9aX C3aX . . 112.91(8) no
    C1X C9aX C3aX . . 105.67(8) no
    C9X C9aX H9a1X . . 107.4(8) no
    C1X C9aX H9a1X . . 110.1(8) no
    C3aX C9aX H9a1X . . 108.3(8) no
    C11X C10X C15X . . 118.53(9) no
    C11X C10X C9X . . 120.17(9) no
    C15X C10X C9X . . 121.27(9) no
    C10X C11X C12X . . 120.68(10) no
    C10X C11X H111X . . 118.9(9) no
    C12X C11X H111X . . 120.5(9) no
    C13X C12X C11X . . 120.31(10) no
    C13X C12X H121X . . 120.4(9) no
    C11X C12X H121X . . 119.3(9) no
    C12X C13X C14X . . 119.59(10) no
    C12X C13X H131X . . 119.2(9) no
    C14X C13X H131X . . 121.2(9) no
    C13X C14X C15X . . 119.99(10) no
    C13X C14X H141X . . 120.7(9) no
    C15X C14X H141X . . 119.3(9) no
    C14X C15X C10X . . 120.89(10) no
    C14X C15X H151X . . 119.0(9) no
    C10X C15X H151X . . 120.1(9) no
    C4X O1X C16X . . 113.00(9) no
    O1X C16X H161X . . 111.0(9) no
    O1X C16X H162X . . 105.3(10) no
    H161X C16X H162X . . 109.3(13) no
    O1X C16X H163X . . 111.8(10) no
    H161X C16X H163X . . 109.5(14) no
    H162X C16X H163X . . 109.8(14) no
    C2Y C1Y C9aY . . 105.37(9) no
    C2Y C1Y H11Y . . 107.9(9) no
    C9aY C1Y H11Y . . 109.3(9) no
    C2Y C1Y H12Y . . 113.1(9) no
    C9aY C1Y H12Y . . 113.2(10) no
    H11Y C1Y H12Y . . 107.8(13) no
    C1Y C2Y C3Y . . 103.01(9) no
    C1Y C2Y H21Y . . 113.4(9) no
    C3Y C2Y H21Y . . 113.9(9) no
    C1Y C2Y H22Y . . 109.8(9) no
    C3Y C2Y H22Y . . 110.3(9) no
    H21Y C2Y H22Y . . 106.4(13) no
    C2Y C3Y C3aY . . 103.70(9) no
    C2Y C3Y H31Y . . 112.0(10) no
    C3aY C3Y H31Y . . 112.8(10) no
    C2Y C3Y H32Y . . 110.5(10) no
    C3aY C3Y H32Y . . 108.7(10) no
    H31Y C3Y H32Y . . 109.1(14) no
    C4Y C3aY C3Y . . 114.90(9) no
    C4Y C3aY C9aY . . 113.56(8) no
    C3Y C3aY C9aY . . 104.37(9) no
    C4Y C3aY H3a1Y . . 106.3(9) no
    C3Y C3aY H3a1Y . . 110.1(9) no
    C9aY C3aY H3a1Y . . 107.5(9) no
    O1Y C4Y C4aY . . 107.09(8) no
    O1Y C4Y C3aY . . 113.08(9) no
    C4aY C4Y C3aY . . 111.73(9) no
    O1Y C4Y H41Y . . 107.9(8) no
    C4aY C4Y H41Y . . 109.0(8) no
    C3aY C4Y H41Y . . 107.9(8) no
    C5Y C4aY C8aY . . 119.91(10) no
    C5Y C4aY C4Y . . 122.41(10) no
    C8aY C4aY C4Y . . 117.63(9) no
    C4aY C5Y C6Y . . 120.41(10) no
    C4aY C5Y H51Y . . 118.8(10) no
    C6Y C5Y H51Y . . 120.8(10) no
    C7Y C6Y C5Y . . 119.79(10) no
    C7Y C6Y H61Y . . 120.3(10) no
    C5Y C6Y H61Y . . 119.9(9) no
    C6Y C7Y C8Y . . 120.03(10) no
    C6Y C7Y H71Y . . 120.9(9) no
    C8Y C7Y H71Y . . 119.0(9) no
    C7Y C8Y C8aY . . 120.60(10) no
    C7Y C8Y H81Y . . 120.1(8) no
    C8aY C8Y H81Y . . 119.3(8) no
    C8Y C8aY C4aY . . 119.27(9) no
    C8Y C8aY C9Y . . 123.96(9) no
    C4aY C8aY C9Y . . 116.77(9) no
    C10Y C9Y C8aY . . 113.42(9) no
    C10Y C9Y C9aY . . 113.05(9) no
    C8aY C9Y C9aY . . 108.44(8) no
    C10Y C9Y H91Y . . 107.1(8) no
    C8aY C9Y H91Y . . 108.0(8) no
    C9aY C9Y H91Y . . 106.5(8) no
    C9Y C9aY C1Y . . 112.67(9) no
    C9Y C9aY C3aY . . 112.37(8) no
    C1Y C9aY C3aY . . 106.04(9) no
    C9Y C9aY H9a1Y . . 108.5(8) no
    C1Y C9aY H9a1Y . . 109.5(8) no
    C3aY C9aY H9a1Y . . 107.7(8) no
    C11Y C10Y C15Y . . 118.30(10) no
    C11Y C10Y C9Y . . 120.01(10) no
    C15Y C10Y C9Y . . 121.67(10) no
    C12Y C11Y C10Y . . 120.93(12) no
    C12Y C11Y H111Y . . 121.0(9) no
    C10Y C11Y H111Y . . 118.1(9) no
    C13Y C12Y C11Y . . 120.18(12) no
    C13Y C12Y H121Y . . 120.6(10) no
    C11Y C12Y H121Y . . 119.2(10) no
    C12Y C13Y C14Y . . 119.51(11) no
    C12Y C13Y H131Y . . 121.3(10) no
    C14Y C13Y H131Y . . 119.2(10) no
    C13Y C14Y C15Y . . 120.41(12) no
    C13Y C14Y H141Y . . 120.1(10) no
    C15Y C14Y H141Y . . 119.4(10) no
    C14Y C15Y C10Y . . 120.67(11) no
    C14Y C15Y H151Y . . 119.6(9) no
    C10Y C15Y H151Y . . 119.7(9) no
    C16Y O1Y C4Y . . 114.91(9) no
    O1Y C16Y H161Y . . 111.5(9) no
    O1Y C16Y H162Y . . 111.5(9) no
    H161Y C16Y H162Y . . 108.4(13) no
    O1Y C16Y H163Y . . 105.0(10) no
    H161Y C16Y H163Y . . 109.0(13) no
    H162Y C16Y H163Y . . 111.5(14) no
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
    C9aX C1X C2X C3X . . . . -35.19(11) no
    C1X C2X C3X C3aX . . . . 40.33(11) no
    C2X C3X C3aX C4X . . . . -154.26(9) no
    C2X C3X C3aX C9aX . . . . -29.95(11) no
    C3X C3aX C4X O1X . . . . -73.07(11) no
    C9aX C3aX C4X O1X . . . . 166.76(8) no
    C3X C3aX C4X C4aX . . . . 161.53(9) no
    C9aX C3aX C4X C4aX . . . . 41.36(11) no
    O1X C4X C4aX C5X . . . . 6.77(14) no
    C3aX C4X C4aX C5X . . . . 129.09(10) no
    O1X C4X C4aX C8aX . . . . -173.95(9) no
    C3aX C4X C4aX C8aX . . . . -51.62(12) no
    C8aX C4aX C5X C6X . . . . -2.70(16) no
    C4X C4aX C5X C6X . . . . 176.56(10) no
    C4aX C5X C6X C7X . . . .  -.94(16) no
    C5X C6X C7X C8X . . . . 3.08(17) no
    C6X C7X C8X C8aX . . . . -1.58(16) no
    C7X C8X C8aX C4aX . . . . -2.05(15) no
    C7X C8X C8aX C9X . . . . 176.87(10) no
    C5X C4aX C8aX C8X . . . . 4.17(15) no
    C4X C4aX C8aX C8X . . . . -175.14(9) no
    C5X C4aX C8aX C9X . . . . -174.82(9) no
    C4X C4aX C8aX C9X . . . . 5.86(13) no
    C8X C8aX C9X C10X . . . . -7.17(14) no
    C4aX C8aX C9X C10X . . . . 171.77(9) no
    C8X C8aX C9X C9aX . . . . -132.71(10) no
    C4aX C8aX C9X C9aX . . . . 46.23(12) no
    C10X C9X C9aX C1X . . . . 61.82(11) no
    C8aX C9X C9aX C1X . . . . -172.34(8) no
    C10X C9X C9aX C3aX . . . . -178.70(8) no
    C8aX C9X C9aX C3aX . . . . -52.86(11) no
    C2X C1X C9aX C9X . . . . 140.17(9) no
    C2X C1X C9aX C3aX . . . . 16.56(11) no
    C4X C3aX C9aX C9X . . . . 9.47(12) no
    C3X C3aX C9aX C9X . . . . -115.07(9) no
    C4X C3aX C9aX C1X . . . . 132.81(9) no
    C3X C3aX C9aX C1X . . . . 8.27(11) no
    C8aX C9X C10X C11X . . . . 102.86(11) no
    C9aX C9X C10X C11X . . . . -133.38(10) no
    C8aX C9X C10X C15X . . . . -74.96(12) no
    C9aX C9X C10X C15X . . . . 48.80(12) no
    C15X C10X C11X C12X . . . .  -.11(15) no
    C9X C10X C11X C12X . . . . -177.99(9) no
    C10X C11X C12X C13X . . . .  .27(16) no
    C11X C12X C13X C14X . . . .  -.22(17) no
    C12X C13X C14X C15X . . . .  .03(17) no
    C13X C14X C15X C10X . . . .  .13(17) no
    C11X C10X C15X C14X . . . .  -.09(15) no
    C9X C10X C15X C14X . . . . 177.77(10) no
    C4aX C4X O1X C16X . . . . -87.95(11) no
    C3aX C4X O1X C16X . . . . 148.01(9) no
    C9aY C1Y C2Y C3Y . . . . -35.95(12) no
    C1Y C2Y C3Y C3aY . . . . 42.38(12) no
    C2Y C3Y C3aY C4Y . . . . -157.19(10) no
    C2Y C3Y C3aY C9aY . . . . -32.17(12) no
    C3Y C3aY C4Y O1Y . . . . -81.70(12) no
    C9aY C3aY C4Y O1Y . . . . 158.24(9) no
    C3Y C3aY C4Y C4aY . . . . 157.39(10) no
    C9aY C3aY C4Y C4aY . . . . 37.33(12) no
    O1Y C4Y C4aY C5Y . . . . 11.04(14) no
    C3aY C4Y C4aY C5Y . . . . 135.38(10) no
    O1Y C4Y C4aY C8aY . . . . -171.39(9) no
    C3aY C4Y C4aY C8aY . . . . -47.05(13) no
    C8aY C4aY C5Y C6Y . . . .  .39(16) no
    C4Y C4aY C5Y C6Y . . . . 177.91(10) no
    C4aY C5Y C6Y C7Y . . . .  -.53(17) no
    C5Y C6Y C7Y C8Y . . . .  .31(17) no
    C6Y C7Y C8Y C8aY . . . .  .06(17) no
    C7Y C8Y C8aY C4aY . . . .  -.20(16) no
    C7Y C8Y C8aY C9Y . . . . -179.97(10) no
    C5Y C4aY C8aY C8Y . . . .  -.03(15) no
    C4Y C4aY C8aY C8Y . . . . -177.66(9) no
    C5Y C4aY C8aY C9Y . . . . 179.76(9) no
    C4Y C4aY C8aY C9Y . . . . 2.12(14) no
    C8Y C8aY C9Y C10Y . . . . -4.42(14) no
    C4aY C8aY C9Y C10Y . . . . 175.81(9) no
    C8Y C8aY C9Y C9aY . . . . -130.87(10) no
    C4aY C8aY C9Y C9aY . . . . 49.35(12) no
    C10Y C9Y C9aY C1Y . . . . 58.49(12) no
    C8aY C9Y C9aY C1Y . . . . -174.85(9) no
    C10Y C9Y C9aY C3aY . . . . 178.21(9) no
    C8aY C9Y C9aY C3aY . . . . -55.13(11) no
    C2Y C1Y C9aY C9Y . . . . 139.17(10) no
    C2Y C1Y C9aY C3aY . . . . 15.86(12) no
    C4Y C3aY C9aY C9Y . . . . 12.41(12) no
    C3Y C3aY C9aY C9Y . . . . -113.46(10) no
    C4Y C3aY C9aY C1Y . . . . 135.91(9) no
    C3Y C3aY C9aY C1Y . . . . 10.05(11) no
    C8aY C9Y C10Y C11Y . . . . 104.92(11) no
    C9aY C9Y C10Y C11Y . . . . -131.11(11) no
    C8aY C9Y C10Y C15Y . . . . -73.50(13) no
    C9aY C9Y C10Y C15Y . . . . 50.48(13) no
    C15Y C10Y C11Y C12Y . . . .  -.17(17) no
    C9Y C10Y C11Y C12Y . . . . -178.64(11) no
    C10Y C11Y C12Y C13Y . . . .  .53(18) no
    C11Y C12Y C13Y C14Y . . . .  -.40(19) no
    C12Y C13Y C14Y C15Y . . . .  -.08(18) no
    C13Y C14Y C15Y C10Y . . . .  .43(18) no
    C11Y C10Y C15Y C14Y . . . .  -.30(16) no
    C9Y C10Y C15Y C14Y . . . . 178.13(10) no
    C4aY C4Y O1Y C16Y . . . . -163.39(9) no
    C3aY C4Y O1Y C16Y . . . . 73.10(12) no
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
    C9aX H9a1X C4aX 2_556  .990(15) 3.109(15) 4.0952(15) 174.3(11) no
    C9aX H9a1X C5X 2_556  .990(15) 3.067(15) 3.9559(15) 150.0(11) yes
    C9aX H9a1X C6X 2_556  .990(15) 3.161(15) 3.8645(15) 129.2(10) no
    C9aX H9a1X C7X 2_556  .990(15) 3.304(15) 3.9312(16) 122.9(10) no
    C9aX H9a1X C8X 2_556  .990(15) 3.301(15) 4.0272(15) 131.6(10) no
    C9aX H9a1X C8aX 2_556  .990(15) 3.190(15) 4.0919(15) 152.1(11) no
    C9aX H9a1X CgAX 2_556  .990(15) 2.87 3.74 147.8 yes
    C6X H61X C10X 1_554  .980(14) 2.974(15) 3.9404(15) 168.9(11) no
    C6X H61X C11X 1_554  .980(14) 2.861(14) 3.6807(15) 141.7(11) yes
    C6X H61X C12X 1_554  .980(14) 2.986(14) 3.6285(16) 124.2(10) no
    C6X H61X C13X 1_554  .980(14) 3.212(14) 3.8428(16) 123.6(10) no
    C6X H61X C14X 1_554  .980(14) 3.304(14) 4.0838(16) 137.8(10) no
    C6X H61X C15X 1_554  .980(14) 3.185(15) 4.1244(16) 161.1(11) no
    C6X H61X CgDX 1_554  .980(14) 2.76 3.63 148.3 yes
    C9aY H9a1Y C4aY 2_666  .995(14) 3.120(14) 4.1140(15) 178.5(11) no
    C9aY H9a1Y C5Y 2_666  .995(14) 3.066(14) 3.9790(16) 153.2(10) yes
    C9aY H9a1Y C6Y 2_666  .995(14) 3.070(14) 3.8155(16) 132.7(10) no
    C9aY H9a1Y C7Y 2_666  .995(14) 3.132(14) 3.7971(16) 125.5(9) no
    C9aY H9a1Y C8Y 2_666  .995(14) 3.185(14) 3.9387(15) 133.8(10) no
    C9aY H9a1Y C8aY 2_666  .995(14) 3.183(14) 4.0974(15) 153.6(10) no
    C9aY H9a1Y CgAY 2_666  .995(14) 2.80 3.71 151.9 yes
    C4Y H41Y C4aY 2_665 1.029(14) 2.840(14) 3.7503(15) 147.6(10) yes
    C4Y H41Y C5Y 2_665 1.029(14) 3.018(14) 4.0270(16) 166.8(10) no
    C4Y H41Y C6Y 2_665 1.029(14) 3.417(14) 4.4286(16) 167.7(10) no
    C4Y H41Y C7Y 2_665 1.029(14) 3.620(14) 4.5532(16) 151.7(10) no
    C4Y H41Y C8Y 2_665 1.029(14) 3.467(14) 4.3041(16) 139.7(10) no
    C4Y H41Y C8aY 2_665 1.029(14) 3.090(14) 3.9033(15) 136.7(10) no
    C4Y H41Y CgAY 2_665 1.029(14) 2.94 3.93 161.8 yes
    C6Y H61Y C10Y 1_655  .966(16) 2.983(17) 3.9331(16) 167.9(12) yes
    C6Y H61Y C11Y 1_655  .966(16) 2.972(16) 3.7786(17) 141.8(12) no
    C6Y H61Y C12Y 1_655  .966(16) 3.002(16) 3.6428(17) 125.0(11) no
    C6Y H61Y C13Y 1_655  .966(16) 3.044(16) 3.6687(17) 123.7(11) no
    C6Y H61Y C14Y 1_655  .966(16) 3.040(16) 3.8147(17) 138.1(12) no
    C6Y H61Y C15Y 1_655  .966(16) 3.004(17) 3.9375(16) 162.8(12) no
    C6Y H61Y CgDY 1_655  .966(16) 2.67 3.53 150.0 yes
    C16X H161X C10Y 2_666 1.014(17) 3.684(16) 4.4842(18) 137.5(11) no
    C16X H161X C11Y 2_666 1.014(17) 3.770(17) 4.729(2) 158.6(11) no
    C16X H161X C12Y 2_666 1.014(17) 3.543(17) 4.494(2) 157.1(12) no
    C16X H161X C13Y 2_666 1.014(17) 3.177(17) 3.951(2) 134.1(11) no
    C16X H161X C14Y 2_666 1.014(17) 3.050(16) 3.6331(18) 117.6(11) yes
    C16X H161X C15Y 2_666 1.014(17) 3.322(16) 3.9295(18) 120.1(11) no
    C16X H161X CgDY 2_666 1.014(17) 3.14 3.99 141.8 yes
