#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209705.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_2209705
loop_
_publ_author_name
'Zhu, Ying-Hong'
'Ma, Chun-An'
'Xu, Ying-Hua'
_publ_section_title
;
 Ethyl
 5-methyl-2,2-diphenylcyclopropanespiro-3(4H)-furan-4-carboxylate
;
_journal_coeditor_code           XU2044
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2795
_journal_page_last               o2796
_journal_paper_doi               10.1107/S1600536806019982
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H22 O3'
_chemical_formula_moiety         'C22 H22 O3'
_chemical_formula_sum            'C22 H22 O3'
_chemical_formula_weight         334.40
_chemical_name_systematic
;
Ethyl 5-methyl-2,2-diphenylcyclopropanespiro-3(4H)-furan-4-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.590(3)
_cell_length_b                   9.979(2)
_cell_length_c                   15.193(3)
_cell_measurement_reflns_used    12979
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1841.2(7)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17549
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.2
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.051
_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)+(0.0784P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.141
_refine_ls_wR_factor_ref         0.152
_reflns_number_gt                3026
_reflns_number_total             4203
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2044.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209705
_cod_database_fobs_code          2209705
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.71613(12) 1.08976(16) 0.42138(11) 0.0838(5) Uani d . 1
O O2 0.54762(12) 1.14001(15) 0.43183(11) 0.0794(4) Uani d . 1
O O3 0.56933(8) 0.84751(10) 0.20118(7) 0.0442(3) Uani d . 1
C C1 0.8815(2) 1.1809(3) 0.51029(19) 0.1053(9) Uani d . 1
H H1A 0.9100 1.0916 0.5226 0.158 Uiso calc R 1
H H1B 0.9147 1.2381 0.5609 0.158 Uiso calc R 1
H H1C 0.8981 1.2141 0.4561 0.158 Uiso calc R 1
C C2 0.7631(2) 1.1790(3) 0.49698(18) 0.0995(9) Uani d . 1
H H2A 0.7454 1.1476 0.5519 0.119 Uiso calc R 1
H H2B 0.7332 1.2686 0.4835 0.119 Uiso calc R 1
C C3 0.60659(15) 1.07904(16) 0.39513(12) 0.0558(4) Uani d . 1
C C4 0.56853(12) 0.98764(15) 0.31789(11) 0.0458(4) Uani d . 1
C C5 0.63025(12) 0.92212(15) 0.27196(11) 0.0458(4) Uani d . 1
C C6 0.75045(14) 0.9152(2) 0.28029(14) 0.0641(5) Uani d . 1
H H6A 0.7774 1.0030 0.2721 0.096 Uiso calc R 1
H H6B 0.7636 0.8560 0.2345 0.096 Uiso calc R 1
H H6C 0.7880 0.8821 0.3397 0.096 Uiso calc R 1
C C7 0.45597(11) 0.83882(13) 0.21238(10) 0.0382(3) Uani d . 1
C C8 0.37645(12) 0.83891(14) 0.11829(10) 0.0409(3) Uani d . 1
C C9 0.40022(15) 0.9096(2) 0.04786(13) 0.0675(6) Uani d . 1
H H9 0.4669 0.9548 0.0576 0.081 Uiso calc R 1
C C10 0.32559(17) 0.9139(2) -0.03732(14) 0.0800(7) Uani d . 1
H H10 0.3428 0.9617 -0.0843 0.096 Uiso calc R 1
C C11 0.22680(15) 0.8485(2) -0.05314(13) 0.0626(5) Uani d . 1
H H11 0.1771 0.8513 -0.1105 0.075 Uiso calc R 1
C C12 0.20212(14) 0.77886(18) 0.01663(12) 0.0569(4) Uani d . 1
H H12 0.1349 0.7349 0.0067 0.068 Uiso calc R 1
C C13 0.27652(12) 0.77351(16) 0.10168(11) 0.0485(4) Uani d . 1
H H13 0.2590 0.7252 0.1483 0.058 Uiso calc R 1
C C14 0.45377(11) 0.70584(13) 0.26227(10) 0.0378(3) Uani d . 1
C C15 0.47766(13) 0.58945(15) 0.22088(12) 0.0494(4) Uani d . 1
H H15 0.4924 0.5947 0.1641 0.059 Uiso calc R 1
C C16 0.47984(15) 0.46628(16) 0.26260(13) 0.0571(4) Uani d . 1
H H16 0.4969 0.3897 0.2343 0.069 Uiso calc R 1
C C17 0.45679(14) 0.45650(16) 0.34598(13) 0.0571(4) Uani d . 1
H H17 0.4574 0.3734 0.3739 0.069 Uiso calc R 1
C C18 0.43284(14) 0.57055(16) 0.38770(12) 0.0546(4) Uani d . 1
H H18 0.4165 0.5643 0.4438 0.066 Uiso calc R 1
C C19 0.43277(12) 0.69507(15) 0.34689(10) 0.0444(4) Uani d . 1
H H19 0.4185 0.7717 0.3766 0.053 Uiso calc R 1
C C20 0.45054(12) 0.96340(14) 0.27020(11) 0.0423(3) Uani d . 1
C C21 0.37512(15) 1.08090(16) 0.23412(14) 0.0588(5) Uani d . 1
H H21A 0.4029 1.1704 0.2516 0.071 Uiso calc R 1
H H21B 0.3264 1.0737 0.1731 0.071 Uiso calc R 1
C C22 0.35302(14) 0.99284(16) 0.30622(13) 0.0543(4) Uani d . 1
H H22A 0.2905 0.9325 0.2890 0.065 Uiso calc R 1
H H22B 0.3670 1.0291 0.3675 0.065 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
C3 O1 C2 117.31(17) ?
C5 O3 C7 107.41(11) ?
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 C1 107.9(2) ?
O1 C2 H2A 110.1 ?
C1 C2 H2A 110.1 ?
O1 C2 H2B 110.1 ?
C1 C2 H2B 110.1 ?
H2A C2 H2B 108.4 ?
O2 C3 O1 122.38(17) ?
O2 C3 C4 125.07(17) ?
O1 C3 C4 112.54(16) ?
C5 C4 C3 127.44(15) ?
C5 C4 C20 107.90(13) ?
C3 C4 C20 124.35(15) ?
C4 C5 O3 113.13(13) ?
C4 C5 C6 133.94(15) ?
O3 C5 C6 112.92(15) ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
O3 C7 C8 107.96(11) ?
O3 C7 C14 104.52(10) ?
C8 C7 C14 111.96(11) ?
O3 C7 C20 101.99(10) ?
C8 C7 C20 114.96(11) ?
C14 C7 C20 114.16(12) ?
C9 C8 C13 118.28(15) ?
C9 C8 C7 120.56(13) ?
C13 C8 C7 121.10(13) ?
C8 C9 C10 120.56(16) ?
C8 C9 H9 119.7 ?
C10 C9 H9 119.7 ?
C11 C10 C9 120.71(17) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 119.15(16) ?
C10 C11 H11 120.4 ?
C12 C11 H11 120.4 ?
C11 C12 C13 120.44(15) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C8 C13 C12 120.86(15) ?
C8 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C19 C14 C15 118.18(13) ?
C19 C14 C7 124.05(13) ?
C15 C14 C7 117.74(13) ?
C16 C15 C14 121.12(16) ?
C16 C15 H15 119.4 ?
C14 C15 H15 119.4 ?
C17 C16 C15 120.18(16) ?
C17 C16 H16 119.9 ?
C15 C16 H16 119.9 ?
C18 C17 C16 119.42(15) ?
C18 C17 H17 120.3 ?
C16 C17 H17 120.3 ?
C17 C18 C19 120.63(16) ?
C17 C18 H18 119.7 ?
C19 C18 H18 119.7 ?
C14 C19 C18 120.45(15) ?
C14 C19 H19 119.8 ?
C18 C19 H19 119.8 ?
C4 C20 C22 126.71(14) ?
C4 C20 C21 119.91(13) ?
C21 C20 C22 59.05(11) yes
C4 C20 C7 102.74(12) ?
C22 C20 C7 122.16(12) ?
C21 C20 C7 122.51(14) ?
C20 C21 C22 59.86(10) yes
C22 C21 H21A 117.8 ?
C20 C21 H21A 117.8 ?
C22 C21 H21B 117.8 ?
C20 C21 H21B 117.8 ?
H21A C21 H21B 114.9 ?
C20 C22 C21 61.08(11) yes
C21 C22 H22A 117.7 ?
C20 C22 H22A 117.7 ?
C21 C22 H22B 117.7 ?
C20 C22 H22B 117.7 ?
H22A C22 H22B 114.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.335(2) ?
O1 C2 1.451(2) ?
O2 C3 1.204(2) ?
O3 C5 1.3653(18) ?
O3 C7 1.4836(16) ?
C1 C2 1.451(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.464(2) ?
C4 C5 1.343(2) ?
C4 C20 1.491(2) ?
C5 C6 1.486(2) ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C7 C8 1.514(2) ?
C7 C14 1.5321(18) ?
C7 C20 1.534(2) ?
C8 C9 1.379(2) ?
C8 C13 1.380(2) ?
C9 C10 1.385(3) ?
C9 H9 0.9300 ?
C10 C11 1.368(3) ?
C10 H10 0.9300 ?
C11 C12 1.370(3) ?
C11 H11 0.9300 ?
C12 C13 1.383(2) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C19 1.383(2) ?
C14 C15 1.391(2) ?
C15 C16 1.380(2) ?
C15 H15 0.9300 ?
C16 C17 1.376(3) ?
C16 H16 0.9300 ?
C17 C18 1.374(3) ?
C17 H17 0.9300 ?
C18 C19 1.389(2) ?
C18 H18 0.9300 ?
C19 H19 0.9300 ?
C20 C22 1.499(2) yes
C20 C21 1.517(2) yes
C21 C22 1.487(3) yes
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127842
