#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/63/2016369.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016369
loop_
_publ_author_name
'Henryk Krawczyk'
'Katarzyna Wąsek'
'Jacek Kędzia'
'Jakub Wojciechowski'
'Wojciech M. Wolf'
_publ_section_title
;
 trans-(1R,2R)-1-Benzyl-2-phenylcyclopropanecarboxylic
 acid
;
_journal_coeditor_code           AV3113
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o24
_journal_page_last               o26
_journal_paper_doi               10.1107/S0108270107050883
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H16 O2'
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_chemical_name_systematic
;rac-trans-(1R,2R)-1-Benzyl-2-phenylcyclopropanecarboxylic
acid
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.3300(10)
_cell_angle_beta                 92.1880(10)
_cell_angle_gamma                97.9650(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9983(2)
_cell_length_b                   9.5439(4)
_cell_length_c                   12.7293(5)
_cell_measurement_reflns_used    5353
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.32
_cell_volume                     669.15(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material
;
SHELXTL (Bruker, 2003) and publCIF (Westrip, 2007)
;
_computing_structure_refinement  'SHELXTL (Bruker, 2003)'
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9804
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count \\infly
_diffrn_standards_interval_time  \\infly
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.8716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SHELXTL; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.051P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2270
_reflns_number_total             2348
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3113.cif
_cod_data_source_block           I
_cod_database_code               2016369
_cod_database_fobs_code          2016369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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)
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
_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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120611
