#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:18:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180177 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/73/7107391.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_7107391
loop_
_publ_author_name
'Gen-Qiang Chen'
'Xiang-Ying Tang'
'Min Shi'
_publ_section_title
;
 HOTf mediated cascade reactions of 1-arenoylcyclopropanecarboxylic acids
 with arenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              2340
_journal_paper_doi               10.1039/c2cc17581a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.653(3)
_cell_length_b                   7.9432(18)
_cell_length_c                   23.492(5)
_cell_measurement_reflns_used    1916
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      23.78
_cell_measurement_theta_min      2.22
_cell_volume                     2734.3(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1099
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17150
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                1810
_reflns_number_total             2685
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc17581a.txt
_cod_data_source_block           dm11379
_cod_original_cell_volume        2734.4(11)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7107391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
O1 O 0.36091(11) 0.1686(2) 0.51603(8) 0.0320(5) Uani 1 1 d .
C1 C 0.39715(16) 0.2857(3) 0.54099(9) 0.0209(6) Uani 1 1 d .
C2 C 0.49553(15) 0.3062(3) 0.55208(9) 0.0177(6) Uani 1 1 d .
C3 C 0.56702(16) 0.1993(3) 0.53706(9) 0.0225(6) Uani 1 1 d .
H3 H 0.5558 0.0979 0.5168 0.027 Uiso 1 1 calc R
C4 C 0.65441(15) 0.2447(3) 0.55226(10) 0.0234(6) Uani 1 1 d .
H4 H 0.7044 0.1747 0.5421 0.028 Uiso 1 1 calc R
C5 C 0.66963(16) 0.3926(3) 0.58243(9) 0.0240(6) Uani 1 1 d .
H5 H 0.7303 0.4220 0.5926 0.029 Uiso 1 1 calc R
C6 C 0.59885(15) 0.4979(3) 0.59803(9) 0.0214(6) Uani 1 1 d .
H6 H 0.6102 0.5972 0.6194 0.026 Uiso 1 1 calc R
C7 C 0.51026(15) 0.4551(3) 0.58166(9) 0.0172(5) Uani 1 1 d .
C8 C 0.42192(14) 0.5538(3) 0.59056(9) 0.0173(5) Uani 1 1 d .
H8 H 0.4239 0.6559 0.5657 0.021 Uiso 1 1 calc R
C9 C 0.34653(15) 0.4339(3) 0.56726(9) 0.0189(6) Uani 1 1 d .
H9 H 0.3116 0.4936 0.5367 0.023 Uiso 1 1 calc R
C10 C 0.27995(15) 0.3731(3) 0.61280(10) 0.0228(6) Uani 1 1 d .
H10A H 0.2499 0.2683 0.5998 0.027 Uiso 1 1 calc R
H10B H 0.2321 0.4592 0.6188 0.027 Uiso 1 1 calc R
C11 C 0.32964(16) 0.3399(3) 0.66899(10) 0.0233(6) Uani 1 1 d .
H11A H 0.2864 0.2930 0.6972 0.028 Uiso 1 1 calc R
H11B H 0.3790 0.2567 0.6629 0.028 Uiso 1 1 calc R
C12 C 0.36943(15) 0.5026(3) 0.69107(9) 0.0192(5) Uani 1 1 d .
C13 C 0.36300(15) 0.5496(3) 0.74850(10) 0.0231(6) Uani 1 1 d .
C14 C 0.39649(15) 0.7051(3) 0.76473(10) 0.0265(6) Uani 1 1 d .
H14 H 0.3939 0.7370 0.8037 0.032 Uiso 1 1 calc R
C15 C 0.43375(16) 0.8153(3) 0.72541(11) 0.0252(6) Uani 1 1 d .
H15 H 0.4548 0.9224 0.7376 0.030 Uiso 1 1 calc R
C16 C 0.44073(15) 0.7712(3) 0.66833(10) 0.0208(6) Uani 1 1 d .
C17 C 0.40995(14) 0.6117(3) 0.65179(9) 0.0167(5) Uani 1 1 d .
C18 C 0.47782(16) 0.8976(3) 0.62616(11) 0.0253(6) Uani 1 1 d .
H18A H 0.4974 0.9992 0.6464 0.038 Uiso 1 1 calc R
H18B H 0.4301 0.9270 0.5987 0.038 Uiso 1 1 calc R
H18C H 0.5300 0.8487 0.6060 0.038 Uiso 1 1 calc R
C19 C 0.31963(18) 0.4353(4) 0.79200(10) 0.0386(8) Uani 1 1 d .
H19A H 0.3263 0.4849 0.8300 0.058 Uiso 1 1 calc R
H19B H 0.3498 0.3252 0.7911 0.058 Uiso 1 1 calc R
H19C H 0.2547 0.4216 0.7832 0.058 Uiso 1 1 calc R
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
O1 C1 C2 126.5(2)
O1 C1 C9 124.9(2)
C2 C1 C9 108.6(2)
C7 C2 C3 121.9(2)
C7 C2 C1 109.5(2)
C3 C2 C1 128.6(2)
C4 C3 C2 118.3(2)
C4 C3 H3 120.9
C2 C3 H3 120.9
C3 C4 C5 120.2(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 121.8(2)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C6 C7 118.5(2)
C5 C6 H6 120.7
C7 C6 H6 120.7
C2 C7 C6 119.3(2)
C2 C7 C8 111.95(19)
C6 C7 C8 128.7(2)
C17 C8 C7 112.48(17)
C17 C8 C9 115.82(18)
C7 C8 C9 103.84(19)
C17 C8 H8 108.1
C7 C8 H8 108.1
C9 C8 H8 108.1
C1 C9 C10 110.5(2)
C1 C9 C8 105.65(18)
C10 C9 C8 113.60(18)
C1 C9 H9 109.0
C10 C9 H9 109.0
C8 C9 H9 109.0
C9 C10 C11 110.79(18)
C9 C10 H10A 109.5
C11 C10 H10A 109.5
C9 C10 H10B 109.5
C11 C10 H10B 109.5
H10A C10 H10B 108.1
C12 C11 C10 109.4(2)
C12 C11 H11A 109.8
C10 C11 H11A 109.8
C12 C11 H11B 109.8
C10 C11 H11B 109.8
H11A C11 H11B 108.2
C17 C12 C13 119.9(2)
C17 C12 C11 117.9(2)
C13 C12 C11 122.2(2)
C14 C13 C12 118.6(2)
C14 C13 C19 120.0(2)
C12 C13 C19 121.3(2)
C13 C14 C15 121.4(2)
C13 C14 H14 119.3
C15 C14 H14 119.3
C14 C15 C16 120.9(2)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C17 118.2(2)
C15 C16 C18 119.4(2)
C17 C16 C18 122.3(2)
C12 C17 C16 121.0(2)
C12 C17 C8 119.1(2)
C16 C17 C8 120.0(2)
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C13 C19 H19A 109.5
C13 C19 H19B 109.5
H19A C19 H19B 109.5
C13 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.221(3)
C1 C2 1.474(3)
C1 C9 1.522(3)
C2 C7 1.389(3)
C2 C3 1.394(3)
C3 C4 1.377(3)
C3 H3 0.9500
C4 C5 1.390(4)
C4 H4 0.9500
C5 C6 1.382(3)
C5 H5 0.9500
C6 C7 1.396(3)
C6 H6 0.9500
C7 C8 1.528(3)
C8 C17 1.520(3)
C8 C9 1.558(3)
C8 H8 1.0000
C9 C10 1.527(3)
C9 H9 1.0000
C10 C11 1.530(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.510(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C17 1.398(3)
C12 C13 1.403(3)
C13 C14 1.382(4)
C13 C19 1.507(4)
C14 C15 1.385(4)
C14 H14 0.9500
C15 C16 1.389(3)
C15 H15 0.9500
C16 C17 1.400(3)
C16 C18 1.512(3)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
