##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-04-06
_journal_date_accepted     2010-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1237
_journal_page_last     o1237
_journal_paper_category     QO
_journal_coeditor_code     HB5399
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
1-(2-Methyl-6-nitro-4-phenyl-3-quinolyl)ethanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wan-Sin Loh'
;
      Thomson Reuters ResearcherID: C-7581-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'K. Kiran' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
    'S. Sarveswari' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
    'V. Vijayakumar' ?
;
      Organic Chemistry Division
      School of Advanced Sciences
      VIT University
      Vellore 632 014, India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(2-Methyl-6-nitro-4-phenyl-3-quinolyl)ethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H14 N2 O3'
_chemical_formula_sum     'C18 H14 N2 O3'
_chemical_formula_iupac     'C18 H14 N2 O3'
_chemical_formula_weight     306.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.297(2)
_cell_length_b     7.7689(12)
_cell_length_c     17.9430(19)
_cell_angle_alpha     90.00
_cell_angle_beta     129.099(7)
_cell_angle_gamma     90.00
_cell_volume     1438.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5914
_cell_measurement_theta_min     3.00
_cell_measurement_theta_max     32.91
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.414
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9541
_exptl_absorpt_correction_T_max     0.9765
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100.00(10)
_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 DUO CCD area-detector diffractometer
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14926
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0364
_diffrn_reflns_theta_min     3.00
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_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 >
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     4148
_reflns_number_gt     3310
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0841
_refine_ls_R_factor_gt     0.0606
_refine_ls_wR_factor_gt     0.1874
_refine_ls_wR_factor_ref     0.2319
_refine_ls_goodness_of_fit_ref     1.127
_refine_ls_restrained_S_all     1.127
_refine_ls_number_reflns     4148
_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)+(0.1525P)²+0.4637P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.858
_refine_diff_density_min     -0.775
_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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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 0.22581(15) 0.7458(2) 0.39046(10) 0.0262(3) Uani d . 1 . .
    O O2 0.17169(14) 1.20721(18) 0.84191(10) 0.0238(3) Uani d . 1 . .
    O O3 0.35548(14) 1.19938(18) 0.86969(10) 0.0229(3) Uani d . 1 . .
    N N1 0.00896(15) 0.73719(17) 0.49922(11) 0.0144(3) Uani d . 1 . .
    N N2 0.24139(16) 1.16058(19) 0.82228(11) 0.0169(3) Uani d . 1 . .
    C C1 0.07078(17) 0.6966(2) 0.46604(12) 0.0142(3) Uani d . 1 . .
    C C2 0.07093(16) 0.8420(2) 0.57827(12) 0.0133(3) Uani d . 1 . .
    C C3 0.00244(17) 0.8836(2) 0.61256(13) 0.0155(3) Uani d . 1 . .
    H H3A -0.0807 0.8404 0.5809 0.019 Uiso calc R 1 . .
    C C4 0.05691(18) 0.9862(2) 0.69126(13) 0.0165(3) Uani d . 1 . .
    H H4A 0.0124 1.0125 0.7140 0.020 Uiso calc R 1 . .
    C C5 0.18211(17) 1.0511(2) 0.73696(12) 0.0149(3) Uani d . 1 . .
    C C6 0.25169(17) 1.0187(2) 0.70594(12) 0.0142(3) Uani d . 1 . .
    H H6A 0.3334 1.0667 0.7374 0.017 Uiso calc R 1 . .
    C C7 0.19679(16) 0.9106(2) 0.62512(12) 0.0132(3) Uani d . 1 . .
    C C8 0.26215(16) 0.8663(2) 0.58772(12) 0.0130(3) Uani d . 1 . .
    C C9 0.19839(17) 0.7586(2) 0.50918(12) 0.0141(3) Uani d . 1 . .
    C C10 0.39210(17) 0.9385(2) 0.62955(12) 0.0144(3) Uani d . 1 . .
    C C11 0.50170(17) 0.9063(2) 0.72397(13) 0.0165(3) Uani d . 1 . .
    H H11A 0.4945 0.8404 0.7637 0.020 Uiso calc R 1 . .
    C C12 0.62200(18) 0.9721(2) 0.75941(13) 0.0189(4) Uani d . 1 . .
    H H12A 0.6946 0.9497 0.8225 0.023 Uiso calc R 1 . .
    C C13 0.63368(18) 1.0716(2) 0.70039(14) 0.0190(4) Uani d . 1 . .
    H H13A 0.7140 1.1152 0.7240 0.023 Uiso calc R 1 . .
    C C14 0.52518(18) 1.1051(2) 0.60658(14) 0.0187(4) Uani d . 1 . .
    H H14A 0.5328 1.1721 0.5674 0.022 Uiso calc R 1 . .
    C C15 0.40435(18) 1.0389(2) 0.57040(13) 0.0173(4) Uani d . 1 . .
    H H15A 0.3320 1.0612 0.5072 0.021 Uiso calc R 1 . .
    C C16 0.26170(18) 0.6954(2) 0.46785(13) 0.0180(4) Uani d . 1 . .
    C C17 0.3644(2) 0.5611(3) 0.52599(15) 0.0257(4) Uani d . 1 . .
    H H17A 0.4068 0.5403 0.4990 0.039 Uiso calc R 1 . .
    H H17B 0.3255 0.4564 0.5252 0.039 Uiso calc R 1 . .
    H H17C 0.4269 0.6005 0.5910 0.039 Uiso calc R 1 . .
    C C18 0.00164(17) 0.5814(2) 0.37966(13) 0.0171(3) Uani d . 1 . .
    H H18A -0.0812 0.5498 0.3610 0.026 Uiso calc R 1 . .
    H H18B 0.0523 0.4796 0.3950 0.026 Uiso calc R 1 . .
    H H18C -0.0104 0.6411 0.3277 0.026 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 0.0330(8) 0.0330(8) 0.0241(7) -0.0058(6) 0.0234(7) -0.0039(6)
    O2 0.0298(8) 0.0284(7) 0.0265(7) 0.0043(6) 0.0240(7) -0.0017(5)
    O3 0.0266(7) 0.0256(7) 0.0232(7) -0.0056(5) 0.0189(6) -0.0054(5)
    N1 0.0177(7) 0.0126(6) 0.0182(7) 0.0002(5) 0.0139(6) 0.0014(5)
    N2 0.0234(8) 0.0166(7) 0.0188(7) 0.0026(5) 0.0172(6) 0.0017(5)
    C1 0.0183(8) 0.0125(7) 0.0168(8) -0.0002(6) 0.0135(7) 0.0006(5)
    C2 0.0163(8) 0.0127(7) 0.0165(7) 0.0017(5) 0.0131(7) 0.0031(5)
    C3 0.0196(8) 0.0139(7) 0.0220(8) 0.0009(6) 0.0174(7) 0.0025(6)
    C4 0.0237(9) 0.0146(7) 0.0227(8) 0.0031(6) 0.0202(7) 0.0032(6)
    C5 0.0205(8) 0.0138(7) 0.0168(8) 0.0019(6) 0.0149(7) 0.0014(6)
    C6 0.0176(8) 0.0135(7) 0.0182(8) 0.0018(6) 0.0144(7) 0.0018(6)
    C7 0.0174(8) 0.0126(7) 0.0163(8) 0.0019(6) 0.0137(7) 0.0023(5)
    C8 0.0144(7) 0.0136(7) 0.0160(7) 0.0012(5) 0.0120(6) 0.0019(5)
    C9 0.0180(8) 0.0140(7) 0.0175(8) 0.0004(6) 0.0145(7) 0.0006(6)
    C10 0.0177(8) 0.0141(7) 0.0191(8) -0.0014(6) 0.0153(7) -0.0026(6)
    C11 0.0198(8) 0.0175(7) 0.0184(8) 0.0002(6) 0.0151(7) -0.0010(6)
    C12 0.0191(8) 0.0208(8) 0.0197(8) -0.0003(6) 0.0136(7) -0.0020(6)
    C13 0.0191(8) 0.0188(8) 0.0280(9) -0.0033(6) 0.0191(8) -0.0048(6)
    C14 0.0235(9) 0.0173(7) 0.0263(9) -0.0019(6) 0.0209(8) -0.0011(6)
    C15 0.0212(9) 0.0176(7) 0.0198(8) 0.0001(6) 0.0161(7) 0.0001(6)
    C16 0.0197(8) 0.0207(8) 0.0218(9) -0.0063(6) 0.0170(7) -0.0076(6)
    C17 0.0224(9) 0.0314(10) 0.0269(10) 0.0037(7) 0.0173(8) -0.0067(8)
    C18 0.0199(8) 0.0155(7) 0.0200(8) -0.0020(6) 0.0145(7) -0.0024(6)
_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
    O1 C16 . 1.214(2) ?
    O2 N2 . 1.2352(19) ?
    O3 N2 . 1.220(2) ?
    N1 C1 . 1.322(2) ?
    N1 C2 . 1.371(2) ?
    N2 C5 . 1.472(2) ?
    C1 C9 . 1.433(2) ?
    C1 C18 . 1.500(2) ?
    C2 C7 . 1.420(2) ?
    C2 C3 . 1.421(2) ?
    C3 C4 . 1.365(2) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.406(2) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.371(2) ?
    C6 C7 . 1.416(2) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.435(2) ?
    C8 C9 . 1.378(2) ?
    C8 C10 . 1.493(2) ?
    C9 C16 . 1.512(2) ?
    C10 C11 . 1.394(3) ?
    C10 C15 . 1.407(2) ?
    C11 C12 . 1.393(2) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.397(3) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.386(3) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.397(2) ?
    C14 H14A . 0.9300 ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.499(3) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 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
    C1 N1 C2 . . 117.97(14) ?
    O3 N2 O2 . . 123.74(15) ?
    O3 N2 C5 . . 118.87(13) ?
    O2 N2 C5 . . 117.39(15) ?
    N1 C1 C9 . . 122.51(15) ?
    N1 C1 C18 . . 117.24(15) ?
    C9 C1 C18 . . 120.25(14) ?
    N1 C2 C7 . . 123.38(14) ?
    N1 C2 C3 . . 116.87(15) ?
    C7 C2 C3 . . 119.74(15) ?
    C4 C3 C2 . . 120.92(16) ?
    C4 C3 H3A . . 119.5 ?
    C2 C3 H3A . . 119.5 ?
    C3 C4 C5 . . 118.26(14) ?
    C3 C4 H4A . . 120.9 ?
    C5 C4 H4A . . 120.9 ?
    C6 C5 C4 . . 123.46(16) ?
    C6 C5 N2 . . 118.22(15) ?
    C4 C5 N2 . . 118.32(14) ?
    C5 C6 C7 . . 118.74(16) ?
    C5 C6 H6A . . 120.6 ?
    C7 C6 H6A . . 120.6 ?
    C6 C7 C2 . . 118.85(14) ?
    C6 C7 C8 . . 123.23(15) ?
    C2 C7 C8 . . 117.91(15) ?
    C9 C8 C7 . . 117.43(15) ?
    C9 C8 C10 . . 120.86(14) ?
    C7 C8 C10 . . 121.67(14) ?
    C8 C9 C1 . . 120.78(14) ?
    C8 C9 C16 . . 121.66(15) ?
    C1 C9 C16 . . 117.51(14) ?
    C11 C10 C15 . . 119.12(16) ?
    C11 C10 C8 . . 122.36(15) ?
    C15 C10 C8 . . 118.50(15) ?
    C12 C11 C10 . . 120.56(16) ?
    C12 C11 H11A . . 119.7 ?
    C10 C11 H11A . . 119.7 ?
    C11 C12 C13 . . 120.11(17) ?
    C11 C12 H12A . . 119.9 ?
    C13 C12 H12A . . 119.9 ?
    C14 C13 C12 . . 119.78(17) ?
    C14 C13 H13A . . 120.1 ?
    C12 C13 H13A . . 120.1 ?
    C13 C14 C15 . . 120.43(16) ?
    C13 C14 H14A . . 119.8 ?
    C15 C14 H14A . . 119.8 ?
    C14 C15 C10 . . 120.00(17) ?
    C14 C15 H15A . . 120.0 ?
    C10 C15 H15A . . 120.0 ?
    O1 C16 C17 . . 123.29(16) ?
    O1 C16 C9 . . 121.18(17) ?
    C17 C16 C9 . . 115.44(15) ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C1 C18 H18A . . 109.5 ?
    C1 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C1 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 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
    C2 N1 C1 C9 . . . . -0.4(2) ?
    C2 N1 C1 C18 . . . . 179.85(14) ?
    C1 N1 C2 C7 . . . . 0.9(2) ?
    C1 N1 C2 C3 . . . . -179.96(14) ?
    N1 C2 C3 C4 . . . . 179.55(15) ?
    C7 C2 C3 C4 . . . . -1.3(2) ?
    C2 C3 C4 C5 . . . . 0.6(2) ?
    C3 C4 C5 C6 . . . . 0.9(3) ?
    C3 C4 C5 N2 . . . . -179.50(15) ?
    O3 N2 C5 C6 . . . . -9.7(2) ?
    O2 N2 C5 C6 . . . . 170.71(15) ?
    O3 N2 C5 C4 . . . . 170.68(15) ?
    O2 N2 C5 C4 . . . . -8.9(2) ?
    C4 C5 C6 C7 . . . . -1.7(3) ?
    N2 C5 C6 C7 . . . . 178.71(14) ?
    C5 C6 C7 C2 . . . . 0.9(2) ?
    C5 C6 C7 C8 . . . . -179.01(15) ?
    N1 C2 C7 C6 . . . . 179.57(15) ?
    C3 C2 C7 C6 . . . . 0.5(2) ?
    N1 C2 C7 C8 . . . . -0.5(2) ?
    C3 C2 C7 C8 . . . . -179.57(14) ?
    C6 C7 C8 C9 . . . . 179.40(15) ?
    C2 C7 C8 C9 . . . . -0.6(2) ?
    C6 C7 C8 C10 . . . . -2.8(2) ?
    C2 C7 C8 C10 . . . . 177.24(14) ?
    C7 C8 C9 C1 . . . . 1.1(2) ?
    C10 C8 C9 C1 . . . . -176.71(15) ?
    C7 C8 C9 C16 . . . . -176.30(15) ?
    C10 C8 C9 C16 . . . . 5.9(2) ?
    N1 C1 C9 C8 . . . . -0.7(3) ?
    C18 C1 C9 C8 . . . . 179.11(15) ?
    N1 C1 C9 C16 . . . . 176.82(15) ?
    C18 C1 C9 C16 . . . . -3.4(2) ?
    C9 C8 C10 C11 . . . . -119.51(18) ?
    C7 C8 C10 C11 . . . . 62.8(2) ?
    C9 C8 C10 C15 . . . . 58.8(2) ?
    C7 C8 C10 C15 . . . . -118.90(17) ?
    C15 C10 C11 C12 . . . . -0.2(2) ?
    C8 C10 C11 C12 . . . . 178.13(15) ?
    C10 C11 C12 C13 . . . . 0.1(3) ?
    C11 C12 C13 C14 . . . . 0.2(3) ?
    C12 C13 C14 C15 . . . . -0.5(3) ?
    C13 C14 C15 C10 . . . . 0.5(3) ?
    C11 C10 C15 C14 . . . . -0.1(2) ?
    C8 C10 C15 C14 . . . . -178.50(15) ?
    C8 C9 C16 O1 . . . . -109.8(2) ?
    C1 C9 C16 O1 . . . . 72.7(2) ?
    C8 C9 C16 C17 . . . . 73.6(2) ?
    C1 C9 C16 C17 . . . . -103.90(19) ?
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
    C3 H3A O2 2_546 0.93 2.56 3.208(3) 127 yes
