##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_audit_creation_method     'manual editing of SHELXL97 .cif files'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-09-11
_journal_date_accepted     2007-10-16
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o24
_journal_page_last     o26
_journal_paper_category     FO
_journal_coeditor_code     AV3113
_publ_contact_author_name     'Dr. Wojciech M. Wolf'
_publ_contact_author_address
; Institute of General and Ecological Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
_publ_contact_author_email     wmwolf@p.lodz.pl
_publ_contact_author_fax     '48(42)313103'
_publ_contact_author_phone     '48(42)313098'
_publ_section_title
;\
rac-trans-(1R,2R)-1-Benzyl-2-\
phenylcyclopropanecarboxylic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Henryk Krawczyk' .
; Institute of Organic Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
    'Katarzyna Wąsek' .
; Institute of Organic Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
    'Jacek Kędzia' .
; Institute of Organic Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
    'Jakub Wojciechowski' .
; Institute of General and Ecological Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
    'Wojciech M. Wolf' .
; Institute of General and Ecological Chemistry
  Technical University of Łódź
  ul. Żeromskiego 116
  90-924 Łódź
  Poland
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
rac-trans-(1R,2R)-1-Benzyl-2-phenylcyclopropanecarboxylic
acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H16 O2'
_chemical_formula_sum     'C17 H16 O2'
_chemical_formula_iupac     'C17 H16 O2'
_chemical_formula_weight     252.30
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.9983(2)
_cell_length_b     9.5439(4)
_cell_length_c     12.7293(5)
_cell_angle_alpha     111.3300(10)
_cell_angle_beta     92.1880(10)
_cell_angle_gamma     97.9650(10)
_cell_volume     669.15(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5353
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     28.14
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.252
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     268
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SHELXTL; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.8716
_exptl_absorpt_correction_T_max     0.9880
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9804
_diffrn_reflns_av_R_equivalents     0.0206
_diffrn_reflns_av_sigmaI/netI     0.0149
_diffrn_reflns_theta_min     1.73
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     \\infly
_diffrn_standards_interval_time     \\infly
_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     2348
_reflns_number_gt     2270
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0444
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.1112
_refine_ls_wR_factor_ref     0.1124
_refine_ls_goodness_of_fit_ref     1.068
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     2348
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.051P)²+0.1541P] 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     0.155
_refine_diff_density_min     -0.135
_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'
    '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, 2003)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2003)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2003)'
_computing_structure_solution     'SHELXTL (Bruker, 2003)'
_computing_structure_refinement     'SHELXTL (Bruker, 2003)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2003)'
_computing_publication_material
;
SHELXTL (Bruker, 2003) and publCIF (Westrip, 2007)
;
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 0.7410(2) 0.89897(14) 0.01402(10) 0.0689(4) Uani d . 1 . .
    H H1 0.819(4) 0.951(3) -0.036(2) 0.121(8) Uiso d . 1 . .
    O O2 1.06628(18) 0.98230(13) 0.12336(9) 0.0604(3) Uani d . 1 . .
    C C1 0.5162(3) 0.79975(19) 0.16732(14) 0.0584(4) Uani d . 1 . .
    H H11 0.4460 0.8013 0.2351 0.070 Uiso calc R 1 . .
    H H12 0.4299 0.8336 0.1177 0.070 Uiso calc R 1 . .
    C C2 0.6461(2) 0.67518(17) 0.11376(12) 0.0511(4) Uani d . 1 . .
    H H3 0.6393 0.6413 0.0310 0.061 Uiso calc R 1 . .
    C C3 0.7705(2) 0.83928(16) 0.17714(11) 0.0449(3) Uani d . 1 . .
    C C4 0.8697(2) 0.91330(16) 0.10207(12) 0.0471(3) Uani d . 1 . .
    C C5 0.9050(2) 0.87711(16) 0.28991(12) 0.0459(3) Uani d . 1 . .
    H H51 0.8406 0.8071 0.3243 0.055 Uiso calc R 1 . .
    H H52 1.0588 0.8603 0.2761 0.055 Uiso calc R 1 . .
    C C6 0.9119(2) 1.03798(16) 0.37287(11) 0.0449(3) Uani d . 1 . .
    C C7 0.7264(3) 1.08002(18) 0.43037(13) 0.0574(4) Uani d . 1 . .
    H H71 0.5951 1.0088 0.4158 0.069 Uiso calc R 1 . .
    C C8 0.7314(3) 1.2252(2) 0.50892(15) 0.0690(5) Uani d . 1 . .
    H H81 0.6039 1.2512 0.5460 0.083 Uiso calc R 1 . .
    C C9 0.9231(4) 1.3310(2) 0.53248(15) 0.0703(5) Uani d . 1 . .
    H H91 0.9275 1.4287 0.5860 0.084 Uiso calc R 1 . .
    C C10 1.1086(3) 1.2917(2) 0.47644(15) 0.0694(5) Uani d . 1 . .
    H H101 1.2397 1.3633 0.4921 0.083 Uiso calc R 1 . .
    C C11 1.1032(3) 1.14665(18) 0.39682(14) 0.0573(4) Uani d . 1 . .
    H H111 1.2304 1.1220 0.3589 0.069 Uiso calc R 1 . .
    C C12 0.6673(3) 0.55238(16) 0.15805(12) 0.0500(4) Uani d . 1 . .
    C C13 0.5043(3) 0.50666(19) 0.21760(15) 0.0634(4) Uani d . 1 . .
    H H131 0.3794 0.5560 0.2338 0.076 Uiso calc R 1 . .
    C C14 0.5247(4) 0.3881(2) 0.25345(17) 0.0789(6) Uani d . 1 . .
    H H141 0.4135 0.3589 0.2938 0.095 Uiso calc R 1 . .
    C C15 0.7056(4) 0.3136(2) 0.23042(17) 0.0783(6) Uani d . 1 . .
    H H151 0.7180 0.2339 0.2546 0.094 Uiso calc R 1 . .
    C C16 0.8681(4) 0.3572(2) 0.17148(17) 0.0766(5) Uani d . 1 . .
    H H161 0.9919 0.3067 0.1552 0.092 Uiso calc R 1 . .
    C C17 0.8500(3) 0.47578(19) 0.13597(15) 0.0649(4) Uani d . 1 . .
    H H171 0.9629 0.5048 0.0964 0.078 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 0.0753(8) 0.0827(8) 0.0588(7) -0.0017(6) -0.0085(6) 0.0449(7)
    O2 0.0594(7) 0.0729(7) 0.0585(7) 0.0039(6) 0.0052(5) 0.0383(6)
    C1 0.0511(9) 0.0707(10) 0.0632(10) 0.0143(7) 0.0056(7) 0.0349(8)
    C2 0.0555(9) 0.0543(8) 0.0429(8) 0.0030(7) 0.0021(6) 0.0201(7)
    C3 0.0495(8) 0.0469(8) 0.0438(7) 0.0114(6) 0.0066(6) 0.0218(6)
    C4 0.0544(9) 0.0465(8) 0.0453(8) 0.0130(6) 0.0039(6) 0.0212(6)
    C5 0.0522(8) 0.0477(8) 0.0459(8) 0.0113(6) 0.0066(6) 0.0255(6)
    C6 0.0542(8) 0.0478(8) 0.0406(7) 0.0090(6) 0.0031(6) 0.0256(6)
    C7 0.0633(10) 0.0568(9) 0.0524(9) 0.0066(7) 0.0125(7) 0.0212(7)
    C8 0.0863(12) 0.0655(11) 0.0567(10) 0.0222(9) 0.0177(9) 0.0201(8)
    C9 0.1087(15) 0.0495(9) 0.0507(9) 0.0138(9) 0.0014(9) 0.0167(7)
    C10 0.0828(12) 0.0574(10) 0.0638(10) -0.0098(9) -0.0095(9) 0.0269(9)
    C11 0.0580(9) 0.0603(9) 0.0562(9) 0.0042(7) 0.0016(7) 0.0269(8)
    C12 0.0593(9) 0.0461(8) 0.0400(7) -0.0008(6) 0.0019(6) 0.0141(6)
    C13 0.0661(10) 0.0619(10) 0.0639(10) 0.0022(8) 0.0126(8) 0.0277(8)
    C14 0.0967(14) 0.0694(12) 0.0762(12) -0.0057(11) 0.0183(11) 0.0398(10)
    C15 0.1142(16) 0.0515(10) 0.0715(12) 0.0048(10) 0.0004(11) 0.0296(9)
    C16 0.0980(14) 0.0596(11) 0.0763(12) 0.0247(10) 0.0106(10) 0.0259(9)
    C17 0.0755(11) 0.0612(10) 0.0625(10) 0.0149(8) 0.0196(8) 0.0256(8)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.481(2) y
    C1 C3 . 1.508(2) y
    C2 C3 . 1.540(2) y
    C2 C12 . 1.491(2) y
    C3 C4 . 1.4779(19) y
    O2 C4 . 1.2362(17) y
    C3 C5 . 1.5152(19) y
    O1 C4 . 1.2901(17) ?
    O1 H1 . 1.02(3) ?
    C1 H11 . 0.9700 ?
    C1 H12 . 0.9700 ?
    C2 H3 . 0.9800 ?
    C5 C6 . 1.508(2) ?
    C5 H51 . 0.9700 ?
    C5 H52 . 0.9700 ?
    C6 C11 . 1.378(2) ?
    C6 C7 . 1.381(2) ?
    C7 C8 . 1.378(2) ?
    C7 H71 . 0.9300 ?
    C8 C9 . 1.365(3) ?
    C8 H81 . 0.9300 ?
    C9 C10 . 1.367(3) ?
    C9 H91 . 0.9300 ?
    C10 C11 . 1.382(2) ?
    C10 H101 . 0.9300 ?
    C11 H111 . 0.9300 ?
    C12 C13 . 1.378(2) ?
    C12 C17 . 1.382(2) ?
    C13 C14 . 1.383(3) ?
    C13 H131 . 0.9300 ?
    C14 C15 . 1.362(3) ?
    C14 H141 . 0.9300 ?
    C15 C16 . 1.363(3) ?
    C15 H151 . 0.9300 ?
    C16 C17 . 1.378(2) ?
    C16 H161 . 0.9300 ?
    C17 H171 . 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
    C2 C1 C3 . . 62.02(10) y
    C1 C2 C3 . . 59.88(10) y
    C1 C3 C2 . . 58.10(10) y
    C4 O1 H1 . . 112.8(14) ?
    C2 C1 H11 . . 117.6 ?
    C3 C1 H11 . . 117.6 ?
    C2 C1 H12 . . 117.6 ?
    C3 C1 H12 . . 117.6 ?
    H11 C1 H12 . . 114.7 ?
    C1 C2 C12 . . 122.77(13) ?
    C12 C2 C3 . . 121.19(12) ?
    C1 C2 H3 . . 114.1 ?
    C12 C2 H3 . . 114.1 ?
    C3 C2 H3 . . 114.1 ?
    C4 C3 C1 . . 117.41(12) ?
    C4 C3 C5 . . 116.29(12) ?
    C1 C3 C5 . . 119.54(12) ?
    C4 C3 C2 . . 113.93(12) ?
    C5 C3 C2 . . 118.79(11) ?
    O2 C4 O1 . . 123.11(13) ?
    O2 C4 C3 . . 120.76(12) ?
    O1 C4 C3 . . 116.12(13) ?
    C6 C5 C3 . . 114.71(11) ?
    C6 C5 H51 . . 108.6 ?
    C3 C5 H51 . . 108.6 ?
    C6 C5 H52 . . 108.6 ?
    C3 C5 H52 . . 108.6 ?
    H51 C5 H52 . . 107.6 ?
    C11 C6 C7 . . 117.59(14) ?
    C11 C6 C5 . . 121.85(13) ?
    C7 C6 C5 . . 120.53(13) ?
    C8 C7 C6 . . 121.44(16) ?
    C8 C7 H71 . . 119.3 ?
    C6 C7 H71 . . 119.3 ?
    C9 C8 C7 . . 120.21(17) ?
    C9 C8 H81 . . 119.9 ?
    C7 C8 H81 . . 119.9 ?
    C8 C9 C10 . . 119.25(17) ?
    C8 C9 H91 . . 120.4 ?
    C10 C9 H91 . . 120.4 ?
    C9 C10 C11 . . 120.65(17) ?
    C9 C10 H101 . . 119.7 ?
    C11 C10 H101 . . 119.7 ?
    C6 C11 C10 . . 120.85(16) ?
    C6 C11 H111 . . 119.6 ?
    C10 C11 H111 . . 119.6 ?
    C13 C12 C17 . . 117.62(15) ?
    C13 C12 C2 . . 122.14(15) ?
    C17 C12 C2 . . 120.19(14) ?
    C12 C13 C14 . . 120.67(18) ?
    C12 C13 H131 . . 119.7 ?
    C14 C13 H131 . . 119.7 ?
    C15 C14 C13 . . 120.83(18) ?
    C15 C14 H141 . . 119.6 ?
    C13 C14 H141 . . 119.6 ?
    C14 C15 C16 . . 119.27(17) ?
    C14 C15 H151 . . 120.4 ?
    C16 C15 H151 . . 120.4 ?
    C15 C16 C17 . . 120.34(19) ?
    C15 C16 H161 . . 119.8 ?
    C17 C16 H161 . . 119.8 ?
    C16 C17 C12 . . 121.27(17) ?
    C16 C17 H171 . . 119.4 ?
    C12 C17 H171 . . 119.4 ?
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
    C1 C3 C4 O2 . . . . 161.92(14) y
    C2 C3 C4 O2 . . . . -132.99(14) y
    C1 C2 C12 C13 . . . . 27.5(2) y
    C1 C2 C12 C17 . . . . -155.23(15) y
    C3 C1 C2 C12 . . . . 109.79(15) ?
    C2 C1 C3 C4 . . . . 102.45(14) ?
    C2 C1 C3 C5 . . . . -107.42(14) ?
    C1 C2 C3 C4 . . . . -108.48(14) ?
    C12 C2 C3 C4 . . . . 139.17(14) ?
    C1 C2 C3 C5 . . . . 108.69(14) ?
    C12 C2 C3 C5 . . . . -3.7(2) ?
    C5 C3 C4 O2 . . . . 10.82(19) ?
    C1 C3 C4 O1 . . . . -19.14(19) ?
    C5 C3 C4 O1 . . . . -170.24(12) ?
    C2 C3 C4 O1 . . . . 45.96(17) ?
    C4 C3 C5 C6 . . . . 69.96(16) ?
    C1 C3 C5 C6 . . . . -80.49(16) ?
    C2 C3 C5 C6 . . . . -148.06(13) ?
    C3 C5 C6 C11 . . . . -106.23(16) ?
    C3 C5 C6 C7 . . . . 75.75(17) ?
    C11 C6 C7 C8 . . . . 0.0(2) ?
    C5 C6 C7 C8 . . . . 178.11(14) ?
    C6 C7 C8 C9 . . . . -0.7(3) ?
    C7 C8 C9 C10 . . . . 0.7(3) ?
    C8 C9 C10 C11 . . . . 0.0(3) ?
    C7 C6 C11 C10 . . . . 0.6(2) ?
    C5 C6 C11 C10 . . . . -177.43(13) ?
    C9 C10 C11 C6 . . . . -0.6(2) ?
    C3 C2 C12 C13 . . . . 99.54(18) ?
    C3 C2 C12 C17 . . . . -83.17(19) ?
    C17 C12 C13 C14 . . . . -0.1(2) ?
    C2 C12 C13 C14 . . . . 177.30(16) ?
    C12 C13 C14 C15 . . . . -0.2(3) ?
    C13 C14 C15 C16 . . . . 0.1(3) ?
    C14 C15 C16 C17 . . . . 0.2(3) ?
    C15 C16 C17 C12 . . . . -0.5(3) ?
    C13 C12 C17 C16 . . . . 0.4(3) ?
    C2 C12 C17 C16 . . . . -176.98(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
    O1 H1 O2 2_775 1.02(3) 1.61(3) 2.629(2) 175(2)
