#------------------------------------------------------------------------------
#$Date: 2023-12-01 09:54:15 +0200 (Fri, 01 Dec 2023) $
#$Revision: 287926 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/73/7107390.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_7107390
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_absolute_configuration ad
_chemical_formula_sum            'C23 H18 O'
_chemical_formula_weight         310.37
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 98.516(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.066(3)
_cell_length_b                   11.863(3)
_cell_length_c                   10.534(2)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.33
_cell_volume                     1614.8(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7068
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3.9(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4154
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0461
_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)+(0.0614P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                3454
_reflns_number_total             4154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc17581a.txt
_cod_data_source_block           mo_dm11356_0m
_cod_original_cell_volume        1614.7(6)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7107390
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'
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 0.15559(12) 0.13603(14) 0.37880(16) 0.0367(4) Uani 1 1 d .
C1 C 0.23506(15) 0.15534(16) 0.45081(19) 0.0245(4) Uani 1 1 d .
C2 C 0.29868(14) 0.25814(16) 0.45502(18) 0.0234(4) Uani 1 1 d .
C3 C 0.28412(16) 0.35107(17) 0.3728(2) 0.0302(5) Uani 1 1 d .
H3 H 0.2293 0.3527 0.3026 0.036 Uiso 1 1 calc R
C4 C 0.35184(17) 0.44033(18) 0.3968(2) 0.0361(5) Uani 1 1 d .
H4 H 0.3446 0.5042 0.3418 0.043 Uiso 1 1 calc R
C5 C 0.43064(17) 0.43717(18) 0.5011(3) 0.0379(5) Uani 1 1 d .
H5 H 0.4764 0.4996 0.5163 0.046 Uiso 1 1 calc R
C6 C 0.44449(15) 0.34476(17) 0.5841(2) 0.0302(4) Uani 1 1 d .
H6 H 0.4982 0.3441 0.6556 0.036 Uiso 1 1 calc R
C7 C 0.37751(13) 0.25379(15) 0.55914(17) 0.0210(4) Uani 1 1 d .
C8 C 0.37500(13) 0.14394(14) 0.63724(17) 0.0187(3) Uani 1 1 d .
C9 C 0.28699(14) 0.07531(15) 0.55471(18) 0.0219(4) Uani 1 1 d .
H9 H 0.3202 0.0132 0.5112 0.026 Uiso 1 1 calc R
C10 C 0.20848(15) 0.02203(17) 0.6303(2) 0.0272(4) Uani 1 1 d .
H10A H 0.1512 -0.0118 0.5704 0.033 Uiso 1 1 calc R
H10B H 0.2421 -0.0385 0.6863 0.033 Uiso 1 1 calc R
C11 C 0.16576(15) 0.11180(18) 0.7120(2) 0.0284(4) Uani 1 1 d .
H11A H 0.1302 0.1710 0.6556 0.034 Uiso 1 1 calc R
H11B H 0.1145 0.0773 0.7606 0.034 Uiso 1 1 calc R
C12 C 0.25149(14) 0.16382(15) 0.80381(18) 0.0226(4) Uani 1 1 d .
C13 C 0.23326(17) 0.19886(16) 0.92589(19) 0.0284(4) Uani 1 1 d .
H13 H 0.1655 0.1928 0.9476 0.034 Uiso 1 1 calc R
C14 C 0.31141(18) 0.24183(17) 1.0148(2) 0.0324(5) Uani 1 1 d .
H14 H 0.2977 0.2657 1.0967 0.039 Uiso 1 1 calc R
C15 C 0.41049(18) 0.24966(18) 0.9831(2) 0.0335(5) Uani 1 1 d .
H15 H 0.4653 0.2779 1.0441 0.040 Uiso 1 1 calc R
C16 C 0.42979(16) 0.21658(17) 0.8629(2) 0.0284(4) Uani 1 1 d .
H16 H 0.4979 0.2228 0.8423 0.034 Uiso 1 1 calc R
C17 C 0.35124(14) 0.17442(14) 0.77163(18) 0.0207(4) Uani 1 1 d .
C18 C 0.47576(13) 0.07600(14) 0.64589(17) 0.0189(3) Uani 1 1 d .
C19 C 0.54787(15) 0.09561(16) 0.56424(19) 0.0252(4) Uani 1 1 d .
H19 H 0.5385 0.1573 0.5062 0.030 Uiso 1 1 calc R
C20 C 0.63415(15) 0.02584(17) 0.5662(2) 0.0287(4) Uani 1 1 d .
H20 H 0.6829 0.0404 0.5097 0.034 Uiso 1 1 calc R
C21 C 0.64880(15) -0.06389(17) 0.6497(2) 0.0275(4) Uani 1 1 d .
H21 H 0.7075 -0.1114 0.6512 0.033 Uiso 1 1 calc R
C22 C 0.57700(17) -0.08425(17) 0.7319(2) 0.0298(5) Uani 1 1 d .
H22 H 0.5864 -0.1463 0.7895 0.036 Uiso 1 1 calc R
C23 C 0.49164(15) -0.01463(16) 0.73029(19) 0.0277(4) Uani 1 1 d .
H23 H 0.4434 -0.0290 0.7875 0.033 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 127.01(19)
O1 C1 C9 125.31(18)
C2 C1 C9 107.69(16)
C7 C2 C3 122.37(18)
C7 C2 C1 109.99(16)
C3 C2 C1 127.60(18)
C4 C3 C2 117.9(2)
C4 C3 H3 121.1
C2 C3 H3 121.1
C3 C4 C5 120.3(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 121.9(2)
C4 C5 H5 119.1
C6 C5 H5 119.1
C7 C6 C5 118.1(2)
C7 C6 H6 120.9
C5 C6 H6 120.9
C6 C7 C2 119.53(17)
C6 C7 C8 128.09(17)
C2 C7 C8 112.34(15)
C18 C8 C17 110.95(15)
C18 C8 C7 112.90(14)
C17 C8 C7 108.38(14)
C18 C8 C9 108.26(14)
C17 C8 C9 113.73(14)
C7 C8 C9 102.42(14)
C10 C9 C1 111.68(16)
C10 C9 C8 114.91(16)
C1 C9 C8 106.65(14)
C10 C9 H9 107.8
C1 C9 H9 107.8
C8 C9 H9 107.8
C11 C10 C9 109.61(16)
C11 C10 H10A 109.7
C9 C10 H10A 109.7
C11 C10 H10B 109.7
C9 C10 H10B 109.7
H10A C10 H10B 108.2
C12 C11 C10 110.49(16)
C12 C11 H11A 109.6
C10 C11 H11A 109.6
C12 C11 H11B 109.6
C10 C11 H11B 109.6
H11A C11 H11B 108.1
C17 C12 C13 119.02(19)
C17 C12 C11 120.93(18)
C13 C12 C11 120.02(18)
C14 C13 C12 121.54(19)
C14 C13 H13 119.2
C12 C13 H13 119.2
C13 C14 C15 119.02(18)
C13 C14 H14 120.5
C15 C14 H14 120.5
C16 C15 C14 120.3(2)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 121.22(19)
C15 C16 H16 119.4
C17 C16 H16 119.4
C16 C17 C12 118.88(18)
C16 C17 C8 119.48(16)
C12 C17 C8 121.62(17)
C19 C18 C23 118.40(16)
C19 C18 C8 122.07(16)
C23 C18 C8 119.29(16)
C18 C19 C20 120.85(18)
C18 C19 H19 119.6
C20 C19 H19 119.6
C21 C20 C19 120.23(19)
C21 C20 H20 119.9
C19 C20 H20 119.9
C20 C21 C22 119.35(18)
C20 C21 H21 120.3
C22 C21 H21 120.3
C23 C22 C21 120.38(18)
C23 C22 H22 119.8
C21 C22 H22 119.8
C22 C23 C18 120.78(18)
C22 C23 H23 119.6
C18 C23 H23 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.214(2)
C1 C2 1.473(3)
C1 C9 1.530(3)
C2 C7 1.390(3)
C2 C3 1.397(3)
C3 C4 1.379(3)
C3 H3 0.9500
C4 C5 1.391(3)
C4 H4 0.9500
C5 C6 1.397(3)
C5 H5 0.9500
C6 C7 1.390(3)
C6 H6 0.9500
C7 C8 1.544(2)
C8 C18 1.535(2)
C8 C17 1.537(3)
C8 C9 1.564(3)
C9 C10 1.526(3)
C9 H9 1.0000
C10 C11 1.526(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.500(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C17 1.400(2)
C12 C13 1.405(3)
C13 C14 1.377(3)
C13 H13 0.9500
C14 C15 1.387(3)
C14 H14 0.9500
C15 C16 1.384(3)
C15 H15 0.9500
C16 C17 1.391(3)
C16 H16 0.9500
C18 C19 1.386(2)
C18 C23 1.391(3)
C19 C20 1.396(3)
C19 H19 0.9500
C20 C21 1.376(3)
C20 H20 0.9500
C21 C22 1.388(3)
C21 H21 0.9500
C22 C23 1.386(3)
C22 H22 0.9500
C23 H23 0.9500
