##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-11-24
_journal_date_accepted     2010-12-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      1
_journal_page_first     o73
_journal_page_last     o73
_journal_paper_category     QO
_journal_coeditor_code     XU5106
_publ_contact_author_name     'Zhao-yang Wang'
_publ_contact_author_address
;
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People's Republic of China
;
_publ_contact_author_email     'wangwangzhaoyang@tom.com'
_publ_contact_author_fax     '86 20 39310187'
_publ_contact_author_phone     '86 20 39310258'
_publ_section_title
;\
(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,\
2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Jian-Hua Fu'
;
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People's Republic of China
;
    'Zhao-Yang Wang'
;
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People's Republic of China
;
    'Fu-Ling Xue'
;
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People's Republic of China
;
    'Jing-Pei Huo'
;
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-
5-[(1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy]furan-2(5H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H26 Cl N O3'
_chemical_formula_sum     'C18 H26 Cl N O3'
_chemical_formula_iupac     'C18 H26 Cl N O3'
_chemical_formula_weight     339.85
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     7.192(2)
_cell_length_b     9.622(3)
_cell_length_c     27.534(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1905.4(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1222
_cell_measurement_theta_min     2.24
_cell_measurement_theta_max     17.50
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.185
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.214
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.952
_exptl_absorpt_correction_T_max     0.966
_exptl_special_details
;
 Data for (I): [α]^20°^D = -45.0° (c 0.557, CH₃CH₂OH); ¹H NMR
(400 MHz, CDCl₃, TMS): 0.791 (3H, d, J = 6.8 Hz, CH₃),
0.823-0.937 (7H, m, CH, 2CH₃),
0.945-1.181 (2H, m, CH₂),
1.298-1.457 (2H, m, 2CH),
1.623-1.704 (2H, m, CH₂),
2.137-2.210 (2H, m, CH₂),
3.576-3.641 (1H, ddd, J = 4.4 Hz,
J = 4.4 Hz,J = 4.4 Hz,CH),
3.997-4.970 (4H, m, 2CH₂),
5.731-5.884 (3H, m, 3CH),
ESI-MS, m/z (%):
Calcd for C₁₈H₂₇ClNO₃⁺([M+H]⁺): 340.16(100.0),
342.16(32.7), Found: 340.24 (100.0), 342.32(38.7).
;
_diffrn_ambient_temperature     298(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 APEXII area-detector'
_diffrn_measurement_method     'φ and ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9627
_diffrn_reflns_av_R_equivalents     0.0528
_diffrn_reflns_av_sigmaI/netI     0.0693
_diffrn_reflns_theta_min     2.24
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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 > 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     3363
_reflns_number_gt     1708
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1148
_refine_ls_R_factor_gt     0.0515
_refine_ls_wR_factor_gt     0.1074
_refine_ls_wR_factor_ref     0.1291
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3363
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0439P)²] 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     0.114
_refine_diff_density_min     -0.135
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1398 Friedel pairs'
_refine_ls_abs_structure_Flack     0.14(12)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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 for Windows (Farrugia, 1997)'
_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
    Cl Cl1 0.78504(18) 0.24214(12) 0.34421(3) 0.1169(5) Uani d . 1 . .
    C C3 0.7443(5) 0.2768(4) 0.24451(11) 0.0695(9) Uani d . 1 . .
    C C4 0.7076(5) 0.1802(4) 0.20226(12) 0.0744(10) Uani d . 1 . .
    H H4 0.5952 0.2084 0.1847 0.089 Uiso calc R 1 . .
    C C5 0.8243(6) 0.1400(4) 0.12119(10) 0.0775(11) Uani d . 1 . .
    H H5 0.7375 0.2071 0.1070 0.093 Uiso calc R 1 . .
    C C1 0.7075(6) 0.0576(5) 0.27315(13) 0.0840(11) Uani d . 1 . .
    C C2 0.7477(5) 0.1979(4) 0.28492(11) 0.0773(10) Uani d . 1 . .
    C C6 1.0128(6) 0.1530(5) 0.09539(12) 0.0901(13) Uani d . 1 . .
    H H6 1.0961 0.0856 0.1108 0.108 Uiso calc R 1 . .
    C C10 0.7420(7) -0.0036(4) 0.11707(11) 0.1015(13) Uani d . 1 . .
    H H10A 0.6212 -0.0050 0.1327 0.122 Uiso calc R 1 . .
    H H10B 0.8216 -0.0695 0.1338 0.122 Uiso calc R 1 . .
    C C7 0.9896(8) 0.1062(5) 0.04242(13) 0.1185(18) Uani d . 1 . .
    H H7A 0.9093 0.1714 0.0256 0.142 Uiso calc R 1 . .
    H H7B 1.1099 0.1076 0.0265 0.142 Uiso calc R 1 . .
    C C11 1.1050(6) 0.2946(6) 0.10072(14) 0.1047(15) Uani d . 1 . .
    H H11 1.0932 0.3206 0.1350 0.126 Uiso calc R 1 . .
    C C9 0.7204(10) -0.0480(5) 0.06354(14) 0.1288(18) Uani d . 1 . .
    H H9 0.6340 0.0161 0.0476 0.155 Uiso calc R 1 . .
    C C8 0.9082(10) -0.0374(7) 0.03860(16) 0.140(2) Uani d . 1 . .
    H H8A 0.9932 -0.1035 0.0532 0.168 Uiso calc R 1 . .
    H H8B 0.8942 -0.0616 0.0046 0.168 Uiso calc R 1 . .
    C C14 1.0115(8) 0.4096(5) 0.07156(16) 0.140(2) Uani d . 1 . .
    H H14A 1.0309 0.3936 0.0375 0.210 Uiso calc R 1 . .
    H H14B 1.0641 0.4978 0.0804 0.210 Uiso calc R 1 . .
    H H14C 0.8805 0.4100 0.0783 0.210 Uiso calc R 1 . .
    C C13 1.3143(7) 0.2870(7) 0.08997(15) 0.160(2) Uani d . 1 . .
    H H13A 1.3696 0.2151 0.1093 0.241 Uiso calc R 1 . .
    H H13B 1.3712 0.3746 0.0977 0.241 Uiso calc R 1 . .
    H H13C 1.3329 0.2667 0.0562 0.241 Uiso calc R 1 . .
    C C12 0.6404(13) -0.1951(7) 0.06041(19) 0.217(4) Uani d . 1 . .
    H H12A 0.6598 -0.2313 0.0283 0.326 Uiso calc R 1 . .
    H H12B 0.5096 -0.1925 0.0673 0.326 Uiso calc R 1 . .
    H H12C 0.7017 -0.2537 0.0836 0.326 Uiso calc R 1 . .
    C C18 0.7548(7) 0.4780(4) 0.18901(13) 0.0971(12) Uani d . 1 . .
    H H18A 0.6422 0.4507 0.1721 0.117 Uiso calc R 1 . .
    H H18B 0.8618 0.4566 0.1689 0.117 Uiso calc R 1 . .
    C C15 0.7871(6) 0.5142(4) 0.27610(13) 0.0967(13) Uani d . 1 . .
    H H15A 0.6884 0.5045 0.2999 0.116 Uiso calc R 1 . .
    H H15B 0.9064 0.5059 0.2923 0.116 Uiso calc R 1 . .
    C C17 0.7505(7) 0.6280(4) 0.20278(19) 0.1103(14) Uani d . 1 . .
    H H17 0.7344 0.7001 0.1807 0.132 Uiso calc R 1 . .
    C C16 0.7720(7) 0.6461(5) 0.2495(2) 0.1092(14) Uani d . 1 . .
    H H16 0.7772 0.7329 0.2643 0.131 Uiso calc R 1 . .
    N N1 0.7681(5) 0.4111(3) 0.23671(9) 0.0791(9) Uani d . 1 . .
    O O3 0.8607(3) 0.1789(2) 0.17127(7) 0.0767(7) Uani d . 1 . .
    O O1 0.6832(4) 0.0450(2) 0.22383(8) 0.0845(8) Uani d . 1 . .
    O O2 0.6958(5) -0.0440(3) 0.29863(9) 0.1111(10) Uani d . 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
    Cl1 0.1428(11) 0.1448(9) 0.0630(6) 0.0000(9) -0.0027(6) -0.0123(6)
    C3 0.057(2) 0.086(2) 0.065(2) 0.002(2) 0.0010(19) -0.009(2)
    C4 0.067(3) 0.089(3) 0.068(2) 0.002(2) 0.002(2) -0.0044(19)
    C5 0.084(3) 0.096(3) 0.053(2) 0.012(2) -0.0074(19) -0.0018(17)
    C1 0.082(3) 0.096(3) 0.074(3) 0.008(3) 0.009(2) 0.003(2)
    C2 0.072(3) 0.100(3) 0.061(2) 0.005(2) 0.001(2) -0.0071(19)
    C6 0.082(3) 0.132(4) 0.056(2) 0.024(3) 0.001(2) 0.000(2)
    C10 0.131(4) 0.107(3) 0.066(2) -0.005(3) -0.007(3) -0.0180(19)
    C7 0.144(5) 0.155(5) 0.057(2) 0.018(4) 0.007(3) -0.011(3)
    C11 0.093(4) 0.161(5) 0.060(2) -0.010(3) 0.009(2) -0.007(3)
    C9 0.182(6) 0.129(4) 0.075(3) -0.010(4) -0.010(4) -0.028(3)
    C8 0.193(7) 0.155(5) 0.071(3) 0.011(5) 0.012(3) -0.038(3)
    C14 0.165(6) 0.146(4) 0.110(3) -0.015(4) 0.009(4) 0.025(3)
    C13 0.098(4) 0.294(8) 0.088(3) -0.019(5) 0.027(3) -0.011(4)
    C12 0.325(10) 0.197(6) 0.130(4) -0.106(7) 0.031(5) -0.073(4)
    C18 0.097(3) 0.098(3) 0.097(3) 0.007(3) 0.010(3) 0.010(2)
    C15 0.082(3) 0.101(3) 0.107(3) -0.010(3) -0.002(3) -0.022(3)
    C17 0.106(4) 0.085(3) 0.141(4) 0.004(3) 0.015(4) 0.016(3)
    C16 0.088(3) 0.088(3) 0.152(4) -0.009(3) 0.003(3) -0.021(3)
    N1 0.081(3) 0.088(2) 0.0686(17) 0.0027(19) 0.0051(18) -0.0100(16)
    O3 0.0764(17) 0.1003(17) 0.0532(13) 0.0049(14) 0.0025(13) -0.0071(12)
    O1 0.097(2) 0.0833(17) 0.0735(15) -0.0071(15) 0.0035(14) -0.0038(13)
    O2 0.136(3) 0.103(2) 0.0939(18) 0.016(2) 0.0152(19) 0.0119(16)
_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
    Cl1 C2 . 1.709(3) ?
    C3 N1 . 1.321(4) ?
    C3 C2 . 1.347(4) ?
    C3 C4 . 1.512(4) ?
    C4 O3 . 1.393(4) ?
    C4 O1 . 1.441(4) ?
    C4 H4 . 0.9800 ?
    C5 O3 . 1.453(3) ?
    C5 C10 . 1.507(5) ?
    C5 C6 . 1.536(5) ?
    C5 H5 . 0.9800 ?
    C1 O2 . 1.206(4) ?
    C1 O1 . 1.375(4) ?
    C1 C2 . 1.418(5) ?
    C6 C11 . 1.522(6) ?
    C6 C7 . 1.535(5) ?
    C6 H6 . 0.9800 ?
    C10 C9 . 1.542(5) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C7 C8 . 1.504(6) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C11 C14 . 1.524(6) ?
    C11 C13 . 1.535(6) ?
    C11 H11 . 0.9800 ?
    C9 C8 . 1.518(7) ?
    C9 C12 . 1.530(7) ?
    C9 H9 . 0.9800 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C18 N1 . 1.466(4) ?
    C18 C17 . 1.492(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C15 C16 . 1.469(6) ?
    C15 N1 . 1.476(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C17 C16 . 1.308(5) ?
    C17 H17 . 0.9300 ?
    C16 H16 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C3 C2 . . 133.1(3) ?
    N1 C3 C4 . . 119.9(3) ?
    C2 C3 C4 . . 107.0(3) ?
    O3 C4 O1 . . 109.9(3) ?
    O3 C4 C3 . . 109.8(3) ?
    O1 C4 C3 . . 105.0(3) ?
    O3 C4 H4 . . 110.7 ?
    O1 C4 H4 . . 110.7 ?
    C3 C4 H4 . . 110.7 ?
    O3 C5 C10 . . 112.2(3) ?
    O3 C5 C6 . . 105.0(3) ?
    C10 C5 C6 . . 112.8(4) ?
    O3 C5 H5 . . 108.9 ?
    C10 C5 H5 . . 108.9 ?
    C6 C5 H5 . . 108.9 ?
    O2 C1 O1 . . 119.6(4) ?
    O2 C1 C2 . . 130.8(3) ?
    O1 C1 C2 . . 109.6(3) ?
    C3 C2 C1 . . 110.1(3) ?
    C3 C2 Cl1 . . 130.7(3) ?
    C1 C2 Cl1 . . 119.2(3) ?
    C11 C6 C7 . . 113.7(4) ?
    C11 C6 C5 . . 114.4(3) ?
    C7 C6 C5 . . 108.6(4) ?
    C11 C6 H6 . . 106.5 ?
    C7 C6 H6 . . 106.5 ?
    C5 C6 H6 . . 106.5 ?
    C5 C10 C9 . . 111.4(3) ?
    C5 C10 H10A . . 109.3 ?
    C9 C10 H10A . . 109.3 ?
    C5 C10 H10B . . 109.3 ?
    C9 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 108.0 ?
    C8 C7 C6 . . 112.2(4) ?
    C8 C7 H7A . . 109.2 ?
    C6 C7 H7A . . 109.2 ?
    C8 C7 H7B . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    C6 C11 C14 . . 114.0(4) ?
    C6 C11 C13 . . 111.5(5) ?
    C14 C11 C13 . . 111.4(5) ?
    C6 C11 H11 . . 106.5 ?
    C14 C11 H11 . . 106.5 ?
    C13 C11 H11 . . 106.5 ?
    C8 C9 C12 . . 111.8(5) ?
    C8 C9 C10 . . 108.9(4) ?
    C12 C9 C10 . . 110.4(4) ?
    C8 C9 H9 . . 108.6 ?
    C12 C9 H9 . . 108.6 ?
    C10 C9 H9 . . 108.6 ?
    C7 C8 C9 . . 112.1(5) ?
    C7 C8 H8A . . 109.2 ?
    C9 C8 H8A . . 109.2 ?
    C7 C8 H8B . . 109.2 ?
    C9 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    C11 C14 H14A . . 109.5 ?
    C11 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C11 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C11 C13 H13A . . 109.5 ?
    C11 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C11 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C9 C12 H12A . . 109.5 ?
    C9 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C9 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N1 C18 C17 . . 101.4(3) ?
    N1 C18 H18A . . 111.5 ?
    C17 C18 H18A . . 111.5 ?
    N1 C18 H18B . . 111.5 ?
    C17 C18 H18B . . 111.5 ?
    H18A C18 H18B . . 109.3 ?
    C16 C15 N1 . . 102.0(3) ?
    C16 C15 H15A . . 111.4 ?
    N1 C15 H15A . . 111.4 ?
    C16 C15 H15B . . 111.4 ?
    N1 C15 H15B . . 111.4 ?
    H15A C15 H15B . . 109.2 ?
    C16 C17 C18 . . 112.1(4) ?
    C16 C17 H17 . . 123.9 ?
    C18 C17 H17 . . 123.9 ?
    C17 C16 C15 . . 112.5(4) ?
    C17 C16 H16 . . 123.7 ?
    C15 C16 H16 . . 123.7 ?
    C3 N1 C18 . . 124.5(3) ?
    C3 N1 C15 . . 123.3(3) ?
    C18 N1 C15 . . 111.7(3) ?
    C4 O3 C5 . . 116.2(3) ?
    C1 O1 C4 . . 108.2(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
    C16 H16 O2 1_565 0.93 2.42 3.320(6) 164
