##############################################################################
###                                                                        ###
###        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     2008-10-14
_journal_date_accepted     2008-10-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2179
_journal_page_last     o2179
_journal_paper_category     QO
_journal_coeditor_code     BI2312
_publ_contact_author_name     'Zhi-Guo Zhu'
_publ_contact_author_address
;
Experimental Center of Medicine
Jilin Medical College
Jilin 132013
People's Republic of China
;
_publ_contact_author_email     wenliangli.chem@gmail.com
_publ_contact_author_fax     +86-432-4560371
_publ_contact_author_phone     +86-432-4560378
_publ_section_title
;
1-Benzoyl-N-phenylcyclopropanecarboxamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Wen-Liang Li'
;
Experimental Center of Medicine
Jilin Medical College
Jilin 132013
People's Republic of China
;
    'Zhi-Guo Zhu'
;
Experimental Center of Medicine
Jilin Medical College
Jilin 132013
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Benzoyl-N-phenylcyclopropanecarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 N O2'
_chemical_formula_sum     'C17 H15 N O2'
_chemical_formula_iupac     'C17 H15 N O2'
_chemical_formula_weight     265.30
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4240(10)
_cell_length_b     9.4730(13)
_cell_length_c     10.8310(15)
_cell_angle_alpha     94.276(2)
_cell_angle_beta     99.313(2)
_cell_angle_gamma     105.773(2)
_cell_volume     717.72(17)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2748
_cell_measurement_theta_min     1.9
_cell_measurement_theta_max     26.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.228
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.981
_exptl_absorpt_correction_T_max     0.986
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     4053
_diffrn_reflns_av_R_equivalents     0.0122
_diffrn_reflns_av_sigmaI/netI     0.0235
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     26.04
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.968
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_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     2748
_reflns_number_gt     2213
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0555
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1089
_refine_ls_wR_factor_ref     0.1187
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     2748
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0561P)²+0.1075P] 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     0.150
_refine_diff_density_min     -0.148
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.054(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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
    C C1 0.4980(2) 0.72180(15) 0.70564(13) 0.0477(4) Uani d . 1 . .
    C C2 0.4788(2) 0.72747(17) 0.83128(14) 0.0511(4) Uani d . 1 . .
    H H2 0.5289 0.6680 0.8832 0.061 Uiso calc R 1 . .
    C C3 0.3862(2) 0.82028(18) 0.87980(16) 0.0603(4) Uani d . 1 . .
    H H3 0.3762 0.8246 0.9644 0.072 Uiso calc R 1 . .
    C C4 0.3088(3) 0.9062(2) 0.8034(2) 0.0735(5) Uani d . 1 . .
    H H4 0.2463 0.9689 0.8361 0.088 Uiso calc R 1 . .
    C C5 0.3235(3) 0.8996(2) 0.6782(2) 0.0811(6) Uani d . 1 . .
    H H5 0.2691 0.9569 0.6263 0.097 Uiso calc R 1 . .
    C C6 0.4180(3) 0.8089(2) 0.62925(16) 0.0658(5) Uani d . 1 . .
    H H6 0.4283 0.8059 0.5447 0.079 Uiso calc R 1 . .
    C C7 0.6119(2) 0.63374(16) 0.65224(13) 0.0498(4) Uani d . 1 . .
    C C8 0.6665(2) 0.51699(16) 0.72240(13) 0.0488(4) Uani d . 1 . .
    C C9 0.8739(2) 0.5593(2) 0.78679(19) 0.0733(5) Uani d . 1 . .
    H H9A 0.9546 0.6558 0.7773 0.088 Uiso calc R 1 . .
    H H9B 0.9038 0.5258 0.8680 0.088 Uiso calc R 1 . .
    C C10 0.8063(3) 0.4471(2) 0.67465(19) 0.0736(5) Uani d . 1 . .
    H H10A 0.7951 0.3450 0.6874 0.088 Uiso calc R 1 . .
    H H10B 0.8459 0.4749 0.5967 0.088 Uiso calc R 1 . .
    C C11 0.5257(2) 0.41812(16) 0.78762(13) 0.0471(4) Uani d . 1 . .
    C C12 0.1879(2) 0.26815(15) 0.74941(13) 0.0455(3) Uani d . 1 . .
    C C13 0.1551(2) 0.27890(19) 0.87138(15) 0.0591(4) Uani d . 1 . .
    H H13 0.2398 0.3500 0.9333 0.071 Uiso calc R 1 . .
    C C14 -0.0041(3) 0.1833(2) 0.90016(17) 0.0742(5) Uani d . 1 . .
    H H14 -0.0252 0.1893 0.9824 0.089 Uiso calc R 1 . .
    C C15 -0.1321(3) 0.0793(2) 0.80958(19) 0.0748(5) Uani d . 1 . .
    H H15 -0.2386 0.0148 0.8303 0.090 Uiso calc R 1 . .
    C C16 -0.1014(3) 0.07135(19) 0.68809(17) 0.0661(5) Uani d . 1 . .
    H H16 -0.1887 0.0021 0.6260 0.079 Uiso calc R 1 . .
    C C17 0.0577(2) 0.16516(16) 0.65724(15) 0.0525(4) Uani d . 1 . .
    H H17 0.0775 0.1592 0.5746 0.063 Uiso calc R 1 . .
    O O1 0.67064(19) 0.66389(14) 0.55579(10) 0.0730(4) Uani d . 1 . .
    O O2 0.56848(17) 0.38898(14) 0.89348(11) 0.0682(4) Uani d . 1 . .
    N N1 0.34958(18) 0.36333(14) 0.71454(11) 0.0503(3) Uani d D 1 . .
    H H1N 0.338(3) 0.368(2) 0.6331(14) 0.076 Uiso d 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
    C1 0.0472(8) 0.0443(8) 0.0446(8) 0.0012(6) 0.0084(6) 0.0072(6)
    C2 0.0540(9) 0.0509(8) 0.0491(8) 0.0119(7) 0.0149(7) 0.0123(7)
    C3 0.0634(10) 0.0598(10) 0.0608(10) 0.0154(8) 0.0239(8) 0.0097(8)
    C4 0.0724(12) 0.0700(12) 0.0874(14) 0.0306(10) 0.0227(10) 0.0127(10)
    C5 0.0869(14) 0.0849(14) 0.0832(14) 0.0441(12) 0.0096(11) 0.0250(11)
    C6 0.0737(12) 0.0677(11) 0.0518(9) 0.0153(9) 0.0059(8) 0.0150(8)
    C7 0.0493(8) 0.0519(8) 0.0394(7) -0.0013(7) 0.0113(6) 0.0034(6)
    C8 0.0442(8) 0.0519(8) 0.0472(8) 0.0079(6) 0.0127(6) 0.0010(6)
    C9 0.0484(10) 0.0856(13) 0.0772(12) 0.0084(9) 0.0073(9) 0.0070(10)
    C10 0.0663(12) 0.0811(13) 0.0827(13) 0.0263(10) 0.0321(10) 0.0088(10)
    C11 0.0494(9) 0.0471(8) 0.0447(8) 0.0116(7) 0.0118(6) 0.0066(6)
    C12 0.0470(8) 0.0430(7) 0.0479(8) 0.0111(6) 0.0141(6) 0.0101(6)
    C13 0.0560(10) 0.0667(10) 0.0486(9) 0.0058(8) 0.0153(7) 0.0028(7)
    C14 0.0724(12) 0.0884(13) 0.0582(10) 0.0057(10) 0.0307(9) 0.0116(9)
    C15 0.0653(11) 0.0684(12) 0.0818(13) -0.0052(9) 0.0304(10) 0.0107(10)
    C16 0.0602(10) 0.0549(10) 0.0724(11) -0.0010(8) 0.0165(9) -0.0017(8)
    C17 0.0556(9) 0.0496(8) 0.0514(8) 0.0108(7) 0.0156(7) 0.0046(7)
    O1 0.0927(9) 0.0769(8) 0.0522(7) 0.0144(7) 0.0360(6) 0.0146(6)
    O2 0.0616(7) 0.0863(9) 0.0541(7) 0.0149(6) 0.0070(5) 0.0249(6)
    N1 0.0510(7) 0.0538(7) 0.0413(7) 0.0039(6) 0.0123(6) 0.0091(6)
_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
    C1 C6 . 1.388(2) ?
    C1 C2 . 1.390(2) ?
    C1 C7 . 1.488(2) ?
    C2 C3 . 1.378(2) ?
    C2 H2 . 0.930 ?
    C3 C4 . 1.370(3) ?
    C3 H3 . 0.930 ?
    C4 C5 . 1.376(3) ?
    C4 H4 . 0.930 ?
    C5 C6 . 1.375(3) ?
    C5 H5 . 0.930 ?
    C6 H6 . 0.930 ?
    C7 O1 . 1.2196(16) ?
    C7 C8 . 1.495(2) ?
    C8 C11 . 1.5080(19) ?
    C8 C10 . 1.510(2) ?
    C8 C9 . 1.514(2) ?
    C9 C10 . 1.476(3) ?
    C9 H9A . 0.970 ?
    C9 H9B . 0.970 ?
    C10 H10A . 0.970 ?
    C10 H10B . 0.970 ?
    C11 O2 . 1.2118(17) ?
    C11 N1 . 1.3566(19) ?
    C12 C13 . 1.383(2) ?
    C12 C17 . 1.383(2) ?
    C12 N1 . 1.4161(18) ?
    C13 C14 . 1.376(2) ?
    C13 H13 . 0.930 ?
    C14 C15 . 1.372(3) ?
    C14 H14 . 0.930 ?
    C15 C16 . 1.371(2) ?
    C15 H15 . 0.930 ?
    C16 C17 . 1.378(2) ?
    C16 H16 . 0.930 ?
    C17 H17 . 0.930 ?
    N1 H1N . 0.879(14) ?
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
    C6 C1 C2 . . 118.62(15) ?
    C6 C1 C7 . . 118.78(14) ?
    C2 C1 C7 . . 122.46(13) ?
    C3 C2 C1 . . 120.68(15) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 120.01(16) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 119.93(18) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C6 C5 C4 . . 120.52(17) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 120.21(17) ?
    C5 C6 H6 . . 119.9 ?
    C1 C6 H6 . . 119.9 ?
    O1 C7 C1 . . 119.69(14) ?
    O1 C7 C8 . . 120.33(14) ?
    C1 C7 C8 . . 119.80(12) ?
    C7 C8 C11 . . 120.13(13) ?
    C7 C8 C10 . . 117.63(13) ?
    C11 C8 C10 . . 114.96(13) ?
    C7 C8 C9 . . 114.24(13) ?
    C11 C8 C9 . . 116.43(14) ?
    C10 C8 C9 . . 58.41(12) ?
    C10 C9 C8 . . 60.64(11) ?
    C10 C9 H9A . . 117.7 ?
    C8 C9 H9A . . 117.7 ?
    C10 C9 H9B . . 117.7 ?
    C8 C9 H9B . . 117.7 ?
    H9A C9 H9B . . 114.8 ?
    C9 C10 C8 . . 60.95(11) ?
    C9 C10 H10A . . 117.7 ?
    C8 C10 H10A . . 117.7 ?
    C9 C10 H10B . . 117.7 ?
    C8 C10 H10B . . 117.7 ?
    H10A C10 H10B . . 114.8 ?
    O2 C11 N1 . . 124.09(13) ?
    O2 C11 C8 . . 122.85(14) ?
    N1 C11 C8 . . 113.04(12) ?
    C13 C12 C17 . . 119.77(14) ?
    C13 C12 N1 . . 121.74(14) ?
    C17 C12 N1 . . 118.46(13) ?
    C14 C13 C12 . . 119.32(16) ?
    C14 C13 H13 . . 120.3 ?
    C12 C13 H13 . . 120.3 ?
    C15 C14 C13 . . 121.14(16) ?
    C15 C14 H14 . . 119.4 ?
    C13 C14 H14 . . 119.4 ?
    C14 C15 C16 . . 119.35(16) ?
    C14 C15 H15 . . 120.3 ?
    C16 C15 H15 . . 120.3 ?
    C15 C16 C17 . . 120.55(16) ?
    C15 C16 H16 . . 119.7 ?
    C17 C16 H16 . . 119.7 ?
    C16 C17 C12 . . 119.85(15) ?
    C16 C17 H17 . . 120.1 ?
    C12 C17 H17 . . 120.1 ?
    C11 N1 C12 . . 126.26(12) ?
    C11 N1 H1N . . 118.1(12) ?
    C12 N1 H1N . . 114.0(12) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . -1.6(2) ?
    C7 C1 C2 C3 . . . . 174.30(14) ?
    C1 C2 C3 C4 . . . . 1.2(3) ?
    C2 C3 C4 C5 . . . . 0.1(3) ?
    C3 C4 C5 C6 . . . . -1.0(3) ?
    C4 C5 C6 C1 . . . . 0.6(3) ?
    C2 C1 C6 C5 . . . . 0.6(3) ?
    C7 C1 C6 C5 . . . . -175.38(16) ?
    C6 C1 C7 O1 . . . . 17.1(2) ?
    C2 C1 C7 O1 . . . . -158.80(15) ?
    C6 C1 C7 C8 . . . . -167.79(14) ?
    C2 C1 C7 C8 . . . . 16.4(2) ?
    O1 C7 C8 C11 . . . . -144.49(15) ?
    C1 C7 C8 C11 . . . . 40.38(19) ?
    O1 C7 C8 C10 . . . . 4.2(2) ?
    C1 C7 C8 C10 . . . . -170.91(14) ?
    O1 C7 C8 C9 . . . . 69.84(19) ?
    C1 C7 C8 C9 . . . . -105.29(16) ?
    C7 C8 C9 C10 . . . . -108.67(15) ?
    C11 C8 C9 C10 . . . . 104.33(16) ?
    C7 C8 C10 C9 . . . . 102.84(16) ?
    C11 C8 C10 C9 . . . . -106.87(16) ?
    C7 C8 C11 O2 . . . . -135.19(16) ?
    C10 C8 C11 O2 . . . . 75.3(2) ?
    C9 C8 C11 O2 . . . . 9.8(2) ?
    C7 C8 C11 N1 . . . . 46.30(18) ?
    C10 C8 C11 N1 . . . . -103.20(16) ?
    C9 C8 C11 N1 . . . . -168.75(14) ?
    C17 C12 C13 C14 . . . . 2.1(3) ?
    N1 C12 C13 C14 . . . . -179.83(16) ?
    C12 C13 C14 C15 . . . . -1.1(3) ?
    C13 C14 C15 C16 . . . . -0.5(3) ?
    C14 C15 C16 C17 . . . . 1.0(3) ?
    C15 C16 C17 C12 . . . . 0.1(3) ?
    C13 C12 C17 C16 . . . . -1.7(2) ?
    N1 C12 C17 C16 . . . . -179.76(14) ?
    O2 C11 N1 C12 . . . . 1.7(2) ?
    C8 C11 N1 C12 . . . . -179.78(13) ?
    C13 C12 N1 C11 . . . . 34.8(2) ?
    C17 C12 N1 C11 . . . . -147.15(15) ?
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
    N1 H1N O1 2_666 0.879(14) 2.030(10)
                                      2.8960(10)
                                               167.00(10)
