##############################################################################
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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2002-12-10
_journal_date_accepted     2003-01-27
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2003
_journal_volume     59
_journal_issue      3
_journal_page_first     o141
_journal_page_last     o143
_journal_paper_category     FO
_publ_contact_author_name     'Dr. D.S.Yufit'
_publ_contact_author_address
;
Chemistry Department,
University of Durham,
South Rd.,
Durham
DH1 3LE
UK
;
_publ_contact_author_email     'd.s.yufit@durham.ac.uk'
_publ_contact_author_fax     '(0191) 374 3745'
_publ_contact_author_phone     '(0191) 374 4704'
_publ_section_title
;
Two diastereomeric 2,2-dihalo-N-(1-phenylethyl)cyclopropane-1-carboxamides
;
loop_
    _publ_author_name
    _publ_author_address
    'Yufit, Dmitrii S.'
;
Department of Chemistry,
University of Durham,
South Road,
Durham DH1 3LE
England
;
    'Howard, Judith A.K.'
;
Department of Chemistry,
University of Durham,
South Road,
Durham DH1 3LE
England
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(1R,1'S)-2',2'-dichloro-N-(1-phenylethyl)cyclopropane-1'-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 Cl2 N O'
_chemical_formula_sum     'C12 H13 Cl2 N O'
_chemical_formula_iupac     'C12 H13 Cl2 N O'
_chemical_formula_weight     258.13
_chemical_melting_point     '138-140'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.4157(3)
_cell_length_b     9.6893(3)
_cell_length_c     13.9473(4)
_cell_angle_alpha     90.00
_cell_angle_beta     92.910(10)
_cell_angle_gamma     90.00
_cell_volume     1270.80(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     999
_cell_measurement_theta_min     10.25
_cell_measurement_theta_max     20.80
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.349
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     536
_exptl_absorpt_coefficient_mu     0.489
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS (Sheldrick, 1998)'
_exptl_absorpt_correction_T_min     0.7991
_exptl_absorpt_correction_T_max     0.9712
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     100(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 SMART CCD 1K'
_diffrn_measurement_method     'ω-scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12790
_diffrn_reflns_av_R_equivalents     0.0337
_diffrn_reflns_av_sigmaI/netI     0.0410
_diffrn_reflns_theta_min     2.55
_diffrn_reflns_theta_max     30.36
_diffrn_reflns_theta_full     30.36
_diffrn_measured_fraction_theta_max     0.927
_diffrn_measured_fraction_theta_full     0.927
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     6176
_reflns_number_gt     5373
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0419
_refine_ls_R_factor_gt     0.0313
_refine_ls_wR_factor_gt     0.0671
_refine_ls_wR_factor_ref     0.0708
_refine_ls_goodness_of_fit_ref     1.017
_refine_ls_restrained_S_all     1.017
_refine_ls_number_reflns     6176
_refine_ls_number_parameters     393
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.04P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.272
_refine_diff_density_min     -0.213
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     -0.01(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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker SMART'
_computing_cell_refinement     'Bruker SMART'
_computing_data_reduction     'Bruker SHELXTL'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material     'Bruker SHELXTL'
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
    Cl1 0.90658(5) 0.95555(5) 0.14039(3) 0.02506(11) Uani d . 1 . . Cl
    Cl2 1.19172(5) 0.92227(5) 0.07430(3) 0.02897(12) Uani d . 1 . . Cl
    Cl3 0.63731(5) 0.19208(5) 0.10898(4) 0.03026(12) Uani d . 1 . . Cl
    Cl4 0.38863(5) 0.25411(5) 0.21764(4) 0.02986(12) Uani d . 1 . . Cl
    O1 1.20002(13) 1.11590(14) -0.11012(9) 0.0215(3) Uani d . 1 . . O
    O2 0.30541(14) 0.56336(16) 0.15745(10) 0.0253(3) Uani d . 1 . . O
    N1 0.99728(17) 1.03222(18) -0.18427(11) 0.0202(3) Uani d . 1 . . N
    N2 0.52478(17) 0.65041(16) 0.19571(11) 0.0184(3) Uani d . 1 . . N
    C1 0.9813(2) 0.8907(2) -0.32829(13) 0.0252(4) Uani d . 1 . . C
    C2 1.0304(2) 0.7553(3) -0.31640(15) 0.0312(5) Uani d . 1 . . C
    C3 0.9560(3) 0.6457(3) -0.35890(17) 0.0362(5) Uani d . 1 . . C
    C4 0.8311(3) 0.6693(2) -0.41342(15) 0.0329(5) Uani d . 1 . . C
    C5 0.7810(3) 0.8027(2) -0.42590(16) 0.0333(5) Uani d . 1 . . C
    C6 0.8554(2) 0.9130(2) -0.38334(16) 0.0303(4) Uani d . 1 . . C
    C7 1.0610(2) 1.0077(2) -0.27739(14) 0.0262(4) Uani d . 1 . . C
    C8 1.0652(3) 1.1418(3) -0.33433(17) 0.0411(6) Uani d . 1 . . C
    C9 1.07273(19) 1.08525(18) -0.10888(12) 0.0173(3) Uani d . 1 . . C
    C10 0.98923(19) 1.10025(19) -0.02023(12) 0.0182(4) Uani d . 1 . . C
    C11 1.0532(2) 1.1791(2) 0.06502(14) 0.0222(4) Uani d . 1 . . C
    C12 1.03969(19) 1.02698(19) 0.07068(13) 0.0184(4) Uani d . 1 . . C
    C21 0.42350(19) 0.72534(19) 0.34949(13) 0.0199(4) Uani d . 1 . . C
    C22 0.3144(2) 0.7995(2) 0.38976(15) 0.0279(4) Uani d . 1 . . C
    C23 0.2760(3) 0.7734(2) 0.48309(16) 0.0353(5) Uani d . 1 . . C
    C24 0.3458(2) 0.6720(3) 0.53688(15) 0.0329(5) Uani d . 1 . . C
    C25 0.4535(2) 0.5956(2) 0.49750(15) 0.0314(5) Uani d . 1 . . C
    C26 0.4919(2) 0.6218(2) 0.40382(14) 0.0257(4) Uani d . 1 . . C
    C27 0.46959(19) 0.7669(2) 0.25029(13) 0.0195(4) Uani d . 1 . . C
    C28 0.5837(2) 0.8802(2) 0.25918(15) 0.0276(4) Uani d . 1 . . C
    C29 0.43618(18) 0.5592(2) 0.15185(12) 0.0188(4) Uani d . 1 . . C
    C30 0.50897(19) 0.4506(2) 0.09521(12) 0.0198(3) Uani d . 1 . . C
    C31 0.4174(2) 0.3562(2) 0.03031(14) 0.0242(4) Uani d . 1 . . C
    C32 0.4880(2) 0.3009(2) 0.11986(13) 0.0210(4) Uani d . 1 . . C
    H1N 0.910(3) 1.019(3) -0.182(2) 0.050(8) Uiso d . 1 . . H
    H2 1.115(3) 0.740(3) -0.2738(17) 0.034(6) Uiso d . 1 . . H
    H3 0.998(3) 0.555(3) -0.3507(19) 0.046(8) Uiso d . 1 . . H
    H4 0.779(3) 0.599(3) -0.4421(18) 0.036(7) Uiso d . 1 . . H
    H5 0.693(3) 0.820(3) -0.4618(18) 0.035(7) Uiso d . 1 . . H
    H6 0.825(3) 1.004(3) -0.3950(19) 0.039(7) Uiso d . 1 . . H
    H7 1.149(3) 0.985(2) -0.2617(16) 0.020(6) Uiso d . 1 . . H
    H81 0.976(3) 1.179(3) -0.3482(16) 0.028(6) Uiso d . 1 . . H
    H82 1.112(3) 1.127(3) -0.393(2) 0.055(8) Uiso d . 1 . . H
    H83 1.113(3) 1.211(3) -0.2974(18) 0.034(6) Uiso d . 1 . . H
    H10 0.886(2) 1.100(2) -0.0321(14) 0.018(5) Uiso d . 1 . . H
    H111 1.142(2) 1.207(2) 0.0581(14) 0.016(5) Uiso d . 1 . . H
    H112 0.988(2) 1.230(2) 0.1018(15) 0.021(5) Uiso d . 1 . . H
    H2N 0.610(3) 0.645(2) 0.1827(17) 0.030(6) Uiso d . 1 . . H
    H22 0.265(3) 0.864(3) 0.3481(18) 0.036(7) Uiso d . 1 . . H
    H23 0.195(3) 0.820(3) 0.5046(19) 0.043(7) Uiso d . 1 . . H
    H24 0.326(3) 0.657(3) 0.6006(18) 0.033(6) Uiso d . 1 . . H
    H25 0.503(3) 0.520(3) 0.5356(17) 0.030(6) Uiso d . 1 . . H
    H26 0.566(3) 0.568(3) 0.3773(17) 0.034(7) Uiso d . 1 . . H
    H27 0.382(2) 0.797(2) 0.2138(15) 0.022(6) Uiso d . 1 . . H
    H281 0.612(2) 0.905(2) 0.1949(14) 0.015(5) Uiso d . 1 . . H
    H282 0.538(3) 0.964(3) 0.2847(17) 0.033(6) Uiso d . 1 . . H
    H283 0.674(3) 0.842(3) 0.3017(19) 0.040(7) Uiso d . 1 . . H
    H30 0.599(2) 0.471(2) 0.0753(14) 0.020(5) Uiso d . 1 . . H
    H311 0.318(3) 0.366(2) 0.0299(17) 0.031(6) Uiso d . 1 . . H
    H312 0.451(2) 0.326(2) -0.0243(16) 0.023(6) Uiso d . 1 . . H
_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 C12 . 1.7661(18) y
    Cl2 C12 . 1.7532(19) y
    Cl3 C32 . 1.769(2) y
    Cl4 C32 . 1.7524(19) y
    O1 C9 . 1.236(2) y
    O2 C29 . 1.238(2) y
    N1 C9 . 1.341(2) y
    N1 C7 . 1.478(2) y
    N1 H1N . 0.84(3) ?
    N2 C29 . 1.341(2) y
    N2 C27 . 1.471(2) y
    N2 H2N . 0.83(3) ?
    C1 C6 . 1.396(3) ?
    C1 C2 . 1.398(3) ?
    C1 C7 . 1.516(3) ?
    C2 C3 . 1.389(4) ?
    C2 H2 . 0.98(2) ?
    C3 C4 . 1.387(4) ?
    C3 H3 . 0.96(3) ?
    C4 C5 . 1.385(3) ?
    C4 H4 . 0.92(3) ?
    C5 C6 . 1.394(3) ?
    C5 H5 . 0.96(2) ?
    C6 H6 . 0.94(3) ?
    C7 C8 . 1.524(3) y
    C7 H7 . 0.87(2) ?
    C8 H81 . 0.92(3) ?
    C8 H82 . 0.96(3) ?
    C8 H83 . 0.94(3) ?
    C9 C10 . 1.506(2) y
    C10 C12 . 1.509(3) y
    C10 C11 . 1.512(3) y
    C10 H10 . 0.98(2) ?
    C11 C12 . 1.482(3) y
    C11 H111 . 0.89(2) ?
    C11 H112 . 0.95(2) ?
    C21 C22 . 1.394(3) ?
    C21 C26 . 1.395(3) ?
    C21 C27 . 1.525(2) ?
    C22 C23 . 1.392(3) ?
    C22 H22 . 0.95(3) ?
    C23 C24 . 1.382(3) ?
    C23 H23 . 0.95(3) ?
    C24 C25 . 1.391(3) ?
    C24 H24 . 0.93(2) ?
    C25 C26 . 1.397(3) ?
    C25 H25 . 1.01(3) ?
    C26 H26 . 0.96(3) ?
    C27 C28 . 1.537(3) ?
    C27 H27 . 0.99(2) ?
    C28 H281 . 0.98(2) ?
    C28 H282 . 1.00(3) ?
    C28 H283 . 1.08(3) ?
    C29 C30 . 1.502(3) y
    C30 C32 . 1.506(3) y
    C30 C31 . 1.523(3) y
    C30 H30 . 0.92(2) ?
    C31 C32 . 1.485(3) y
    C31 H311 . 0.94(3) ?
    C31 H312 . 0.89(2) ?
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
    C9 N1 C7 . . 121.88(16) y
    C9 N1 H1N . . 121(2) ?
    C7 N1 H1N . . 117(2) ?
    C29 N2 C27 . . 120.91(15) y
    C29 N2 H2N . . 116.3(17) ?
    C27 N2 H2N . . 122.0(17) ?
    C6 C1 C2 . . 118.5(2) ?
    C6 C1 C7 . . 121.9(2) ?
    C2 C1 C7 . . 119.54(19) ?
    C3 C2 C1 . . 120.7(2) ?
    C3 C2 H2 . . 121.2(15) ?
    C1 C2 H2 . . 118.0(15) ?
    C4 C3 C2 . . 120.2(2) ?
    C4 C3 H3 . . 122.9(17) ?
    C2 C3 H3 . . 116.8(17) ?
    C5 C4 C3 . . 119.8(2) ?
    C5 C4 H4 . . 117.5(16) ?
    C3 C4 H4 . . 122.7(16) ?
    C4 C5 C6 . . 120.1(2) ?
    C4 C5 H5 . . 120.8(16) ?
    C6 C5 H5 . . 119.1(16) ?
    C5 C6 C1 . . 120.7(2) ?
    C5 C6 H6 . . 120.5(16) ?
    C1 C6 H6 . . 118.7(16) ?
    N1 C7 C1 . . 108.55(16) ?
    N1 C7 C8 . . 110.07(19) ?
    C1 C7 C8 . . 114.76(18) ?
    N1 C7 H7 . . 104.0(14) ?
    C1 C7 H7 . . 111.5(15) ?
    C8 C7 H7 . . 107.5(15) ?
    C7 C8 H81 . . 113.3(15) ?
    C7 C8 H82 . . 110.1(19) ?
    H81 C8 H82 . . 109(2) ?
    C7 C8 H83 . . 110.1(15) ?
    H81 C8 H83 . . 104(2) ?
    H82 C8 H83 . . 110(2) ?
    O1 C9 N1 . . 123.83(16) y
    O1 C9 C10 . . 122.38(16) y
    N1 C9 C10 . . 113.76(15) y
    C9 C10 C12 . . 119.31(15) y
    C9 C10 C11 . . 119.40(16) y
    C12 C10 C11 . . 58.74(12) y
    C9 C10 H10 . . 114.7(12) ?
    C12 C10 H10 . . 114.2(12) ?
    C11 C10 H10 . . 119.0(12) ?
    C12 C11 C10 . . 60.51(12) y
    C12 C11 H111 . . 113.0(14) ?
    C10 C11 H111 . . 114.0(13) ?
    C12 C11 H112 . . 115.1(13) ?
    C10 C11 H112 . . 116.3(12) ?
    H111 C11 H112 . . 122.4(18) ?
    C11 C12 C10 . . 60.75(12) y
    C11 C12 Cl2 . . 120.34(14) ?
    C10 C12 Cl2 . . 121.22(13) ?
    C11 C12 Cl1 . . 118.96(14) ?
    C10 C12 Cl1 . . 116.43(13) ?
    Cl2 C12 Cl1 . . 111.01(10) y
    C22 C21 C26 . . 118.74(18) ?
    C22 C21 C27 . . 118.61(17) ?
    C26 C21 C27 . . 122.54(16) ?
    C23 C22 C21 . . 121.0(2) ?
    C23 C22 H22 . . 123.2(15) ?
    C21 C22 H22 . . 115.7(15) ?
    C24 C23 C22 . . 119.9(2) ?
    C24 C23 H23 . . 122.2(16) ?
    C22 C23 H23 . . 117.5(16) ?
    C23 C24 C25 . . 120.01(19) ?
    C23 C24 H24 . . 121.2(15) ?
    C25 C24 H24 . . 118.7(15) ?
    C24 C25 C26 . . 120.1(2) ?
    C24 C25 H25 . . 120.6(14) ?
    C26 C25 H25 . . 119.3(14) ?
    C21 C26 C25 . . 120.31(19) ?
    C21 C26 H26 . . 120.3(15) ?
    C25 C26 H26 . . 119.4(15) ?
    N2 C27 C21 . . 113.04(15) ?
    N2 C27 C28 . . 109.02(15) ?
    C21 C27 C28 . . 110.20(15) ?
    N2 C27 H27 . . 105.6(13) ?
    C21 C27 H27 . . 106.1(12) ?
    C28 C27 H27 . . 112.8(13) ?
    C27 C28 H281 . . 109.0(12) ?
    C27 C28 H282 . . 107.6(14) ?
    H281 C28 H282 . . 105.7(18) ?
    C27 C28 H283 . . 109.2(14) ?
    H281 C28 H283 . . 110.1(18) ?
    H282 C28 H283 . . 115(2) ?
    O2 C29 N2 . . 123.17(17) y
    O2 C29 C30 . . 122.52(17) y
    N2 C29 C30 . . 114.31(15) y
    C29 C30 C32 . . 119.10(15) y
    C29 C30 C31 . . 118.25(16) y
    C32 C30 C31 . . 58.73(12) y
    C29 C30 H30 . . 117.3(14) ?
    C32 C30 H30 . . 113.9(14) ?
    C31 C30 H30 . . 116.6(13) ?
    C32 C31 C30 . . 60.07(13) y
    C32 C31 H311 . . 116.4(15) ?
    C30 C31 H311 . . 118.5(15) ?
    C32 C31 H312 . . 116.1(14) ?
    C30 C31 H312 . . 119.7(14) ?
    H311 C31 H312 . . 115(2) ?
    C31 C32 C30 . . 61.21(13) y
    C31 C32 Cl4 . . 120.90(14) ?
    C30 C32 Cl4 . . 120.53(13) ?
    C31 C32 Cl3 . . 117.83(14) ?
    C30 C32 Cl3 . . 116.14(13) ?
    Cl4 C32 Cl3 . . 111.76(11) y
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 . . . . 0.4(3) ?
    C7 C1 C2 C3 . . . . 177.26(19) ?
    C1 C2 C3 C4 . . . . -0.4(3) ?
    C2 C3 C4 C5 . . . . 0.4(3) ?
    C3 C4 C5 C6 . . . . -0.4(3) ?
    C4 C5 C6 C1 . . . . 0.4(3) ?
    C2 C1 C6 C5 . . . . -0.4(3) ?
    C7 C1 C6 C5 . . . . -177.18(19) ?
    C9 N1 C7 C1 . . . . 152.73(18) y
    C9 N1 C7 C8 . . . . -80.9(2) y
    C6 C1 C7 N1 . . . . 84.2(2) y
    C2 C1 C7 N1 . . . . -92.5(2) y
    C6 C1 C7 C8 . . . . -39.4(3) ?
    C2 C1 C7 C8 . . . . 143.9(2) ?
    C7 N1 C9 O1 . . . . -1.0(3) ?
    C7 N1 C9 C10 . . . . -179.11(17) ?
    O1 C9 C10 C12 . . . . -57.0(2) ?
    N1 C9 C10 C12 . . . . 121.17(18) ?
    O1 C9 C10 C11 . . . . 11.5(3) ?
    N1 C9 C10 C11 . . . . -170.34(17) ?
    C9 C10 C11 C12 . . . . -108.37(18) ?
    C10 C11 C12 Cl2 . . . . 111.14(16) ?
    C10 C11 C12 Cl1 . . . . -105.85(15) ?
    C9 C10 C12 C11 . . . . 108.53(19) ?
    C9 C10 C12 Cl2 . . . . -1.2(2) ?
    C11 C10 C12 Cl2 . . . . -109.73(17) ?
    C9 C10 C12 Cl1 . . . . -141.51(15) ?
    C11 C10 C12 Cl1 . . . . 109.96(16) ?
    C26 C21 C22 C23 . . . . 1.4(3) ?
    C27 C21 C22 C23 . . . . -174.7(2) ?
    C21 C22 C23 C24 . . . . -0.4(4) ?
    C22 C23 C24 C25 . . . . -0.5(4) ?
    C23 C24 C25 C26 . . . . 0.4(3) ?
    C22 C21 C26 C25 . . . . -1.4(3) ?
    C27 C21 C26 C25 . . . . 174.55(19) ?
    C24 C25 C26 C21 . . . . 0.5(3) ?
    C29 N2 C27 C21 . . . . 78.3(2) y
    C29 N2 C27 C28 . . . . -158.78(17) y
    C22 C21 C27 N2 . . . . -150.49(18) y
    C26 C21 C27 N2 . . . . 33.6(2) y
    C22 C21 C27 C28 . . . . 87.2(2) ?
    C26 C21 C27 C28 . . . . -88.7(2) ?
    C27 N2 C29 O2 . . . . -3.0(3) ?
    C27 N2 C29 C30 . . . . 177.14(15) ?
    O2 C29 C30 C32 . . . . -58.4(2) ?
    N2 C29 C30 C32 . . . . 121.48(18) ?
    O2 C29 C30 C31 . . . . 9.6(3) ?
    N2 C29 C30 C31 . . . . -170.57(16) ?
    C29 C30 C31 C32 . . . . -108.63(18) ?
    C30 C31 C32 Cl4 . . . . 110.27(17) ?
    C30 C31 C32 Cl3 . . . . -106.16(16) ?
    C29 C30 C32 C31 . . . . 107.21(19) ?
    C29 C30 C32 Cl4 . . . . -3.7(2) ?
    C31 C30 C32 Cl4 . . . . -110.87(17) ?
    C29 C30 C32 Cl3 . . . . -143.90(14) ?
    C31 C30 C32 Cl3 . . . . 108.89(16) ?
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 O2 2_655 0.84(3) 2.11(3) 2.909(2) 158(3)
    N2 H2N O1 2_745 0.83(3) 2.12(3) 2.927(2) 163(2)
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1R,1'R)-2',2'-difluoro-N-(1-phenylethyl)cyclopropane-1'-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 F2 N O'
_chemical_formula_sum     'C12 H13 F2 N O'
_chemical_formula_iupac     'C12 H13 F2 N O'
_chemical_formula_weight     225.23
_chemical_melting_point        .103E-104
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.2402(4)
_cell_length_b     14.2669(5)
_cell_length_c     9.3542(4)
_cell_angle_alpha     90.00
_cell_angle_beta     109.330(10)
_cell_angle_gamma     90.00
_cell_volume     1163.60(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     998
_cell_measurement_theta_min     10.2
_cell_measurement_theta_max     20.8
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.286
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(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 SMART CCD 1K'
_diffrn_measurement_method     'ω-scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11953
_diffrn_reflns_av_R_equivalents     0.0513
_diffrn_reflns_av_sigmaI/netI     0.0767
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     30.33
_diffrn_reflns_theta_full     30.33
_diffrn_measured_fraction_theta_max     0.923
_diffrn_measured_fraction_theta_full     0.923
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_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     5647
_reflns_number_gt     3738
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0918
_refine_ls_R_factor_gt     0.0454
_refine_ls_wR_factor_gt     0.0729
_refine_ls_wR_factor_ref     0.0844
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     5647
_refine_ls_number_parameters     393
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'calc w = 1/[σ²(Fo²)+(0.034P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.152
_refine_diff_density_min     -0.220
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     1.0(5)
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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'Bruker SMART'
_computing_cell_refinement     'Bruker SMART'
_computing_data_reduction     'Bruker SHELXTL'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material     'Bruker SHELXTL'
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
    F1 0.62539(16) 0.03015(10) 0.25394(15) 0.0418(4) Uani d . 1 . . F
    F2 0.86380(16) 0.01065(10) 0.39734(15) 0.0474(4) Uani d . 1 . . F
    F3 0.09259(16) -0.01905(10) -0.28357(15) 0.0429(4) Uani d . 1 . . F
    F4 0.31949(17) -0.07215(10) -0.26885(15) 0.0458(4) Uani d . 1 . . F
    O1 0.58366(17) 0.17844(11) 0.01546(16) 0.0304(4) Uani d . 1 . . O
    O2 0.08026(16) 0.06551(10) 0.00394(16) 0.0323(4) Uani d . 1 . . O
    N1 0.7615(2) 0.11682(13) -0.0752(2) 0.0281(4) Uani d . 1 . . N
    N2 0.2897(2) 0.15807(13) 0.0464(2) 0.0297(5) Uani d . 1 . . N
    C1 0.7271(2) 0.23260(15) -0.2767(2) 0.0243(5) Uani d . 1 . . C
    C2 0.6215(3) 0.30311(17) -0.3392(3) 0.0347(6) Uani d . 1 . . C
    C3 0.6697(3) 0.38934(18) -0.3742(3) 0.0418(6) Uani d . 1 . . C
    C4 0.8227(3) 0.40720(19) -0.3474(3) 0.0383(6) Uani d . 1 . . C
    C5 0.9285(3) 0.33740(17) -0.2860(3) 0.0325(5) Uani d . 1 . . C
    C6 0.8821(3) 0.25057(16) -0.2524(2) 0.0284(5) Uani d . 1 . . C
    C7 0.6765(3) 0.13861(16) -0.2341(2) 0.0265(5) Uani d . 1 . . C
    C8 0.6945(3) 0.05950(18) -0.3362(3) 0.0352(6) Uani d . 1 . . C
    C9 0.7113(2) 0.14259(15) 0.0375(2) 0.0238(5) Uani d . 1 . . C
    C10 0.8187(3) 0.12467(17) 0.1938(2) 0.0303(5) Uani d . 1 . . C
    C11 0.7812(3) 0.17008(19) 0.3279(3) 0.0383(6) Uani d . 1 . . C
    C12 0.7657(2) 0.07081(17) 0.3017(2) 0.0302(5) Uani d . 1 . . C
    C21 0.2263(2) 0.23036(15) 0.2604(2) 0.0279(5) Uani d . 1 . . C
    C22 0.2869(3) 0.15399(17) 0.3511(3) 0.0329(5) Uani d . 1 . . C
    C23 0.2774(3) 0.14595(19) 0.4957(3) 0.0382(6) Uani d . 1 . . C
    C24 0.2075(3) 0.21638(18) 0.5516(3) 0.0418(7) Uani d . 1 . . C
    C25 0.1485(3) 0.29374(19) 0.4625(3) 0.0430(7) Uani d . 1 . . C
    C26 0.1568(3) 0.30095(17) 0.3182(3) 0.0363(6) Uani d . 1 . . C
    C27 0.2263(3) 0.24080(16) 0.0975(3) 0.0313(5) Uani d . 1 . . C
    C28 0.3135(4) 0.3266(2) 0.0746(4) 0.0447(7) Uani d . 1 . . C
    C29 0.2132(3) 0.07792(16) 0.0046(2) 0.0265(5) Uani d . 1 . . C
    C30 0.3009(3) 0.00220(15) -0.0419(2) 0.0283(5) Uani d . 1 . . C
    C31 0.2391(3) -0.09912(17) -0.0495(3) 0.0347(6) Uani d . 1 . . C
    C32 0.2288(3) -0.04759(16) -0.1862(2) 0.0327(6) Uani d . 1 . . C
    H1N 0.846(3) 0.0975(16) -0.058(2) 0.027(7) Uiso d . 1 . . H
    H2 0.513(3) 0.2879(17) -0.357(3) 0.042(7) Uiso d . 1 . . H
    H3 0.596(3) 0.4392(19) -0.419(3) 0.054(8) Uiso d . 1 . . H
    H4 0.852(3) 0.467(2) -0.363(3) 0.058(8) Uiso d . 1 . . H
    H5 1.032(3) 0.3490(19) -0.266(3) 0.049(8) Uiso d . 1 . . H
    H6 0.956(3) 0.1994(16) -0.210(2) 0.032(6) Uiso d . 1 . . H
    H7 0.574(2) 0.1453(14) -0.242(2) 0.015(5) Uiso d . 1 . . H
    H81 0.663(3) 0.0009(18) -0.308(2) 0.033(6) Uiso d . 1 . . H
    H82 0.638(3) 0.0739(16) -0.445(3) 0.032(6) Uiso d . 1 . . H
    H83 0.799(3) 0.0540(19) -0.329(3) 0.056(8) Uiso d . 1 . . H
    H10 0.916(3) 0.1185(16) 0.204(2) 0.029(6) Uiso d . 1 . . H
    H111 0.863(3) 0.1903(16) 0.415(3) 0.030(6) Uiso d . 1 . . H
    H112 0.691(3) 0.206(2) 0.298(3) 0.060(9) Uiso d . 1 . . H
    H2N 0.374(3) 0.1623(17) 0.036(3) 0.034(7) Uiso d . 1 . . H
    H22 0.330(3) 0.1057(16) 0.308(3) 0.033(6) Uiso d . 1 . . H
    H23 0.311(3) 0.0875(18) 0.554(3) 0.037(7) Uiso d . 1 . . H
    H24 0.208(3) 0.2097(17) 0.649(3) 0.039(7) Uiso d . 1 . . H
    H25 0.099(3) 0.3375(18) 0.497(3) 0.040(7) Uiso d . 1 . . H
    H26 0.117(3) 0.3559(19) 0.258(3) 0.038(7) Uiso d . 1 . . H
    H27 0.115(3) 0.2499(16) 0.028(3) 0.034(6) Uiso d . 1 . . H
    H281 0.306(3) 0.3286(19) -0.037(3) 0.055(8) Uiso d . 1 . . H
    H282 0.415(3) 0.3261(18) 0.145(3) 0.037(7) Uiso d . 1 . . H
    H283 0.269(3) 0.383(2) 0.094(3) 0.052(8) Uiso d . 1 . . H
    H30 0.410(3) 0.0101(16) -0.011(2) 0.035(6) Uiso d . 1 . . H
    H311 0.142(3) -0.1015(17) -0.018(3) 0.048(7) Uiso d . 1 . . H
    H312 0.306(3) -0.145(2) -0.024(3) 0.049(8) Uiso d . 1 . . H
_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
    F1 C12 . 1.354(3) y
    F2 C12 . 1.350(3) y
    F3 C32 . 1.350(3) y
    F4 C32 . 1.361(2) y
    O1 C9 . 1.238(2) y
    O2 C29 . 1.239(2) y
    N1 C9 . 1.336(3) y
    N1 C7 . 1.467(3) y
    N1 H1N . 0.79(2) ?
    N2 C29 . 1.333(3) y
    N2 C27 . 1.466(3) y
    N2 H2N . 0.82(2) ?
    C1 C2 . 1.389(3) ?
    C1 C6 . 1.398(3) ?
    C1 C7 . 1.516(3) ?
    C2 C3 . 1.384(3) ?
    C2 H2 . 0.99(3) ?
    C3 C4 . 1.375(4) ?
    C3 H3 . 0.98(3) ?
    C4 C5 . 1.381(4) ?
    C4 H4 . 0.92(3) ?
    C5 C6 . 1.381(3) ?
    C5 H5 . 0.92(3) ?
    C6 H6 . 0.99(2) ?
    C7 C8 . 1.522(3) ?
    C7 H7 . 0.93(2) ?
    C8 H81 . 0.95(2) ?
    C8 H82 . 1.00(2) ?
    C8 H83 . 0.95(3) ?
    C9 C10 . 1.493(3) y
    C10 C12 . 1.476(3) y
    C10 C11 . 1.549(3) y
    C10 H10 . 0.88(2) ?
    C11 C12 . 1.436(4) y
    C11 H111 . 0.96(2) ?
    C11 H112 . 0.94(3) ?
    C21 C22 . 1.380(3) ?
    C21 C26 . 1.396(3) ?
    C21 C27 . 1.531(3) ?
    C22 C23 . 1.390(3) ?
    C22 H22 . 0.95(2) ?
    C23 C24 . 1.387(3) ?
    C23 H23 . 0.99(3) ?
    C24 C25 . 1.382(4) ?
    C24 H24 . 0.91(2) ?
    C25 C26 . 1.381(4) ?
    C25 H25 . 0.89(3) ?
    C26 H26 . 0.96(3) ?
    C27 C28 . 1.520(4) ?
    C27 H27 . 1.02(2) ?
    C28 H281 . 1.03(3) ?
    C28 H282 . 0.95(3) ?
    C28 H283 . 0.95(3) ?
    C29 C30 . 1.499(3) y
    C30 C32 . 1.474(3) y
    C30 C31 . 1.547(3) y
    C30 H30 . 0.96(2) ?
    C31 C32 . 1.450(3) y
    C31 H311 . 1.03(3) ?
    C31 H312 . 0.88(3) ?
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
    C9 N1 C7 . . 122.16(19) y
    C9 N1 H1N . . 121.0(16) ?
    C7 N1 H1N . . 115.8(16) ?
    C29 N2 C27 . . 123.78(19) y
    C29 N2 H2N . . 117.5(17) ?
    C27 N2 H2N . . 118.6(17) ?
    C2 C1 C6 . . 118.4(2) ?
    C2 C1 C7 . . 121.10(19) ?
    C6 C1 C7 . . 120.54(19) ?
    C3 C2 C1 . . 120.5(2) ?
    C3 C2 H2 . . 123.1(14) ?
    C1 C2 H2 . . 116.4(14) ?
    C4 C3 C2 . . 120.9(3) ?
    C4 C3 H3 . . 118.2(15) ?
    C2 C3 H3 . . 120.9(15) ?
    C3 C4 C5 . . 119.1(2) ?
    C3 C4 H4 . . 119.0(17) ?
    C5 C4 H4 . . 121.7(17) ?
    C4 C5 C6 . . 120.8(2) ?
    C4 C5 H5 . . 119.8(17) ?
    C6 C5 H5 . . 119.4(17) ?
    C5 C6 C1 . . 120.4(2) ?
    C5 C6 H6 . . 121.9(13) ?
    C1 C6 H6 . . 117.7(13) ?
    N1 C7 C1 . . 110.21(18) ?
    N1 C7 C8 . . 110.21(19) ?
    C1 C7 C8 . . 112.56(17) ?
    N1 C7 H7 . . 107.0(11) ?
    C1 C7 H7 . . 106.4(12) ?
    C8 C7 H7 . . 110.2(12) ?
    C7 C8 H81 . . 111.6(13) ?
    C7 C8 H82 . . 111.0(13) ?
    H81 C8 H82 . . 111.0(19) ?
    C7 C8 H83 . . 109.7(16) ?
    H81 C8 H83 . . 108(2) ?
    H82 C8 H83 . . 105(2) ?
    O1 C9 N1 . . 122.85(19) y
    O1 C9 C10 . . 121.45(18) y
    N1 C9 C10 . . 115.70(19) y
    C12 C10 C9 . . 119.69(19) y
    C12 C10 C11 . . 56.63(16) y
    C9 C10 C11 . . 117.8(2) y
    C12 C10 H10 . . 115.8(15) ?
    C9 C10 H10 . . 116.7(14) ?
    C11 C10 H10 . . 116.8(14) ?
    C12 C11 C10 . . 59.09(16) y
    C12 C11 H111 . . 116.7(13) ?
    C10 C11 H111 . . 119.5(13) ?
    C12 C11 H112 . . 117.1(17) ?
    C10 C11 H112 . . 113.6(17) ?
    H111 C11 H112 . . 118(2) ?
    F2 C12 F1 . . 107.82(18) y
    F2 C12 C11 . . 120.5(2) ?
    F1 C12 C11 . . 120.6(2) ?
    F2 C12 C10 . . 118.81(19) ?
    F1 C12 C10 . . 119.73(18) ?
    C11 C12 C10 . . 64.28(17) y
    C22 C21 C26 . . 118.4(2) ?
    C22 C21 C27 . . 123.70(19) ?
    C26 C21 C27 . . 117.8(2) ?
    C21 C22 C23 . . 121.3(2) ?
    C21 C22 H22 . . 117.1(13) ?
    C23 C22 H22 . . 121.5(13) ?
    C24 C23 C22 . . 119.6(3) ?
    C24 C23 H23 . . 120.4(13) ?
    C22 C23 H23 . . 119.7(13) ?
    C25 C24 C23 . . 119.4(2) ?
    C25 C24 H24 . . 123.7(16) ?
    C23 C24 H24 . . 116.8(16) ?
    C26 C25 C24 . . 120.7(2) ?
    C26 C25 H25 . . 120.0(16) ?
    C24 C25 H25 . . 119.2(16) ?
    C25 C26 C21 . . 120.4(2) ?
    C25 C26 H26 . . 120.0(14) ?
    C21 C26 H26 . . 119.5(14) ?
    N2 C27 C28 . . 108.37(19) ?
    N2 C27 C21 . . 112.17(19) ?
    C28 C27 C21 . . 113.2(2) ?
    N2 C27 H27 . . 108.4(12) ?
    C28 C27 H27 . . 105.8(13) ?
    C21 C27 H27 . . 108.6(12) ?
    C27 C28 H281 . . 107.7(16) ?
    C27 C28 H282 . . 110.1(15) ?
    H281 C28 H282 . . 115(2) ?
    C27 C28 H283 . . 111.8(17) ?
    H281 C28 H283 . . 107(2) ?
    H282 C28 H283 . . 105(2) ?
    O2 C29 N2 . . 123.5(2) y
    O2 C29 C30 . . 121.7(2) y
    N2 C29 C30 . . 114.75(19) y
    C32 C30 C29 . . 119.3(2) y
    C32 C30 C31 . . 57.31(15) y
    C29 C30 C31 . . 117.4(2) y
    C32 C30 H30 . . 116.1(13) ?
    C29 C30 H30 . . 116.4(13) ?
    C31 C30 H30 . . 117.3(14) ?
    C32 C31 C30 . . 58.81(16) y
    C32 C31 H311 . . 117.2(14) ?
    C30 C31 H311 . . 111.1(14) ?
    C32 C31 H312 . . 117.0(18) ?
    C30 C31 H312 . . 117.8(19) ?
    H311 C31 H312 . . 120(2) ?
    F3 C32 F4 . . 107.82(17) y
    F3 C32 C31 . . 121.5(2) ?
    F4 C32 C31 . . 119.8(2) ?
    F3 C32 C30 . . 120.68(19) ?
    F4 C32 C30 . . 117.9(2) ?
    C31 C32 C30 . . 63.88(16) y
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 . . . . -1.0(3) ?
    C7 C1 C2 C3 . . . . 178.5(2) ?
    C1 C2 C3 C4 . . . . -0.3(4) ?
    C2 C3 C4 C5 . . . . 0.6(4) ?
    C3 C4 C5 C6 . . . . 0.3(4) ?
    C4 C5 C6 C1 . . . . -1.6(3) ?
    C2 C1 C6 C5 . . . . 1.9(3) ?
    C7 C1 C6 C5 . . . . -177.56(19) ?
    C9 N1 C7 C1 . . . . 89.8(2) y
    C9 N1 C7 C8 . . . . -145.3(2) y
    C2 C1 C7 N1 . . . . -125.6(2) y
    C6 C1 C7 N1 . . . . 53.8(2) y
    C2 C1 C7 C8 . . . . 110.9(2) ?
    C6 C1 C7 C8 . . . . -69.7(3) ?
    C7 N1 C9 O1 . . . . 7.1(3) ?
    C7 N1 C9 C10 . . . . -173.47(19) ?
    O1 C9 C10 C12 . . . . 53.3(3) ?
    N1 C9 C10 C12 . . . . -126.2(2) ?
    O1 C9 C10 C11 . . . . -12.2(3) ?
    N1 C9 C10 C11 . . . . 168.3(2) ?
    C9 C10 C11 C12 . . . . 108.8(2) ?
    C10 C11 C12 F2 . . . . 109.7(2) ?
    C10 C11 C12 F1 . . . . -110.8(2) ?
    C9 C10 C12 F2 . . . . 142.3(2) ?
    C11 C10 C12 F2 . . . . -112.2(3) ?
    C9 C10 C12 F1 . . . . 6.6(3) ?
    C11 C10 C12 F1 . . . . 112.1(3) ?
    C9 C10 C12 C11 . . . . -105.5(3) ?
    C26 C21 C22 C23 . . . . 1.1(3) ?
    C27 C21 C22 C23 . . . . -176.9(2) ?
    C21 C22 C23 C24 . . . . -0.8(4) ?
    C22 C23 C24 C25 . . . . -0.1(4) ?
    C23 C24 C25 C26 . . . . 0.8(4) ?
    C24 C25 C26 C21 . . . . -0.6(4) ?
    C22 C21 C26 C25 . . . . -0.4(3) ?
    C27 C21 C26 C25 . . . . 177.7(2) ?
    C29 N2 C27 C28 . . . . -157.5(2) y
    C29 N2 C27 C21 . . . . 76.8(3) y
    C22 C21 C27 N2 . . . . 3.4(3) y
    C26 C21 C27 N2 . . . . -174.6(2) y
    C22 C21 C27 C28 . . . . -119.6(3) ?
    C26 C21 C27 C28 . . . . 62.4(3) ?
    C27 N2 C29 O2 . . . . 0.4(3) ?
    C27 N2 C29 C30 . . . . -179.36(19) ?
    O2 C29 C30 C32 . . . . 50.0(3) ?
    N2 C29 C30 C32 . . . . -130.3(2) ?
    O2 C29 C30 C31 . . . . -16.0(3) ?
    N2 C29 C30 C31 . . . . 163.7(2) ?
    C29 C30 C31 C32 . . . . 108.8(2) ?
    C30 C31 C32 F3 . . . . -111.5(2) ?
    C30 C31 C32 F4 . . . . 108.6(2) ?
    C29 C30 C32 F3 . . . . 7.2(3) ?
    C31 C30 C32 F3 . . . . 112.7(2) ?
    C29 C30 C32 F4 . . . . 143.0(2) ?
    C31 C30 C32 F4 . . . . -111.6(2) ?
    C29 C30 C32 C31 . . . . -105.5(2) ?
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 O2 1_655 0.79(2) 2.10(2) 2.884(2) 171(2)
    N2 H2N O1 . 0.82(2) 2.02(3) 2.840(2) 177(2)
