#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:58:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180204 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/98/7109817.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7109817
loop_
_publ_author_name
'Chuanling Song'
'Di Sun'
'Xianglong Peng'
'Jing Bai'
'Rongyi Zhang'
'Shengzhen Hou'
'Jianwu Wang'
'Zhenghu Xu'
_publ_section_title
;
 Dimerization of cyclopropenes to bifurans using tandem metal relay
 catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              9167
_journal_paper_doi               10.1039/c3cc44762f
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C22 H30 O8'
_chemical_formula_weight         422.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 110.560(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.579(7)
_cell_length_b                   4.8945(14)
_cell_length_c                   22.195(7)
_cell_measurement_temperature    298(2)
_cell_volume                     2296.6(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5338
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9862
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0431
_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)+(0.0581P)²+0.5440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1350
_reflns_number_total             2015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44762f.txt
_cod_data_source_block           p
_cod_database_code               7109817
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.10951(9) 0.2801(4) -0.01775(10) 0.0475(5) Uani 1 1 d .
C2 C 0.06488(9) 0.1308(4) -0.06294(9) 0.0446(5) Uani 1 1 d .
C3 C 0.00456(9) 0.2192(4) -0.05989(9) 0.0417(5) Uani 1 1 d .
C4 C 0.01797(8) 0.4157(4) -0.01403(9) 0.0397(5) Uani 1 1 d .
C5 C 0.20716(11) 0.4767(6) 0.04705(13) 0.0878(9) Uani 1 1 d .
H5A H 0.1934 0.6570 0.0313 0.132 Uiso 1 1 calc R
H5B H 0.2515 0.4580 0.0543 0.132 Uiso 1 1 calc R
H5C H 0.2000 0.4474 0.0867 0.132 Uiso 1 1 calc R
C6 C 0.07769(11) -0.0710(4) -0.10532(10) 0.0563(6) Uani 1 1 d .
C7 C -0.05945(10) 0.1065(5) -0.09890(10) 0.0487(5) Uani 1 1 d .
H7A H -0.0877(10) 0.127(4) -0.0739(10) 0.058 Uiso 1 1 d .
H7B H -0.0543(9) -0.102(4) -0.1048(9) 0.058 Uiso 1 1 d .
C8 C -0.09016(11) 0.2368(5) -0.16479(11) 0.0611(6) Uani 1 1 d .
H8A H -0.0927(10) 0.439(5) -0.1608(10) 0.073 Uiso 1 1 d .
H8B H -0.0606(11) 0.228(4) -0.1895(10) 0.073 Uiso 1 1 d .
C9 C -0.15455(13) 0.1138(7) -0.20115(14) 0.0824(9) Uani 1 1 d .
H9A H -0.1471(13) -0.083(6) -0.2058(13) 0.099 Uiso 1 1 d .
H9B H -0.1823(13) 0.145(6) -0.1773(13) 0.099 Uiso 1 1 d .
C10 C -0.18551(14) 0.2263(7) -0.26776(14) 0.1176(13) Uani 1 1 d .
H10A H -0.1592 0.1903 -0.2928 0.176 Uiso 1 1 calc R
H10B H -0.1911 0.4199 -0.2654 0.176 Uiso 1 1 calc R
H10C H -0.2260 0.1407 -0.2877 0.176 Uiso 1 1 calc R
C11 C 0.0435(2) -0.3504(11) -0.1951(2) 0.0760(15) Uani 0.50 1 d P
H11A H 0.0047 -0.3899 -0.2296 0.114 Uiso 0.50 1 calc PR
H11B H 0.0618 -0.5173 -0.1740 0.114 Uiso 0.50 1 calc PR
H11C H 0.0725 -0.2632 -0.2120 0.114 Uiso 0.50 1 calc PR
C11A C 0.1455(3) -0.3415(11) -0.1361(3) 0.0834(16) Uani 0.50 1 d P
H11D H 0.1320 -0.2762 -0.1796 0.125 Uiso 0.50 1 calc PR
H11E H 0.1222 -0.5031 -0.1342 0.125 Uiso 0.50 1 calc PR
H11F H 0.1899 -0.3834 -0.1216 0.125 Uiso 0.50 1 calc PR
O1 O 0.08349(6) 0.4564(3) 0.01284(6) 0.0469(4) Uani 1 1 d .
O2 O 0.17218(6) 0.2783(3) 0.00035(7) 0.0673(5) Uani 1 1 d .
O5 O 0.03105(8) -0.1734(4) -0.15007(8) 0.0763(5) Uani 1 1 d .
O9 O 0.13448(8) -0.1367(4) -0.09590(8) 0.0821(6) Uani 1 1 d .
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_site_symmetry_3
O2 C1 O1 117.16(17) .
O2 C1 C2 130.91(19) .
O1 C1 C2 111.92(17) .
C1 C2 C3 105.65(17) .
C1 C2 C6 125.15(19) .
C3 C2 C6 129.19(18) .
C4 C3 C2 106.29(16) .
C4 C3 C7 127.48(18) .
C2 C3 C7 126.20(18) .
C3 C4 O1 110.16(15) .
C3 C4 C4 136.0(2) 5_565
O1 C4 C4 113.85(19) 5_565
O2 C5 H5A 109.5 .
O2 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
O2 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
O9 C6 O5 122.9(2) .
O9 C6 C2 118.9(2) .
O5 C6 C2 118.2(2) .
C3 C7 C8 114.89(18) .
C3 C7 H7A 108.6(12) .
C8 C7 H7A 109.3(12) .
C3 C7 H7B 107.7(11) .
C8 C7 H7B 108.9(11) .
H7A C7 H7B 107.1(16) .
C9 C8 C7 111.9(2) .
C9 C8 H8A 111.5(13) .
C7 C8 H8A 110.6(13) .
C9 C8 H8B 112.9(13) .
C7 C8 H8B 110.0(13) .
H8A C8 H8B 99.4(19) .
C10 C9 C8 114.0(3) .
C10 C9 H9A 107.0(16) .
C8 C9 H9A 106.0(16) .
C10 C9 H9B 108.4(17) .
C8 C9 H9B 109.3(17) .
H9A C9 H9B 112(2) .
C9 C10 H10A 109.5 .
C9 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C9 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
O5 C11 H11A 109.5 .
O5 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
O5 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
O9 C11A H11D 109.5 .
O9 C11A H11E 109.5 .
H11D C11A H11E 109.5 .
O9 C11A H11F 109.5 .
H11D C11A H11F 109.5 .
H11E C11A H11F 109.5 .
C1 O1 C4 105.97(14) .
C1 O2 C5 118.09(17) .
C6 O5 C11 118.4(3) .
C6 O9 C11A 117.8(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.328(2) .
C1 O1 1.353(2) .
C1 C2 1.359(3) .
C2 C3 1.453(3) .
C2 C6 1.461(3) .
C3 C4 1.355(3) .
C3 C7 1.505(3) .
C4 O1 1.402(2) .
C4 C4 1.443(4) 5_565
C5 O2 1.437(3) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 O9 1.266(3) .
C6 O5 1.270(3) .
C7 C8 1.521(3) .
C7 H7A 0.99(2) .
C7 H7B 1.04(2) .
C8 C9 1.518(3) .
C8 H8A 1.00(2) .
C8 H8B 1.00(2) .
C9 C10 1.501(4) .
C9 H9A 0.99(3) .
C9 H9B 0.96(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 O5 1.423(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C11A O9 1.421(5) .
C11A H11D 0.9600 .
C11A H11E 0.9600 .
C11A H11F 0.9600 .
