#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:36:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180189 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/85/7108516.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_7108516
loop_
_publ_author_name
'Hai-Tao Zhu'
'Xue Dong'
'Li-Jing Wang'
'Mei-Jin Zhong'
'Xue-Yuan Liu'
'Yong-Min Liang'
_publ_section_title
;
 Facile synthesis of 2-iodo-spiro[indene-1,1'-isobenzofuran]-3'-ones via
 iodine-promoted cascade cyclization
;
_journal_name_full               Chem.Commun.
_journal_page_first              10748
_journal_paper_doi               10.1039/c2cc36127b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C22 H13 I O2'
_chemical_formula_weight         436.22
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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                98.526(3)
_cell_angle_beta                 93.088(3)
_cell_angle_gamma                117.892(2)
_cell_formula_units_Z            2
_cell_length_a                   9.369(2)
_cell_length_b                   9.971(2)
_cell_length_c                   10.815(4)
_cell_measurement_reflns_used    3595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.36
_cell_volume                     874.3(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6204
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    1.843
_exptl_absorpt_correction_T_max  0.7209
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0205P)²+0.7985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0624
_reflns_number_gt                2771
_reflns_number_total             3182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36127b.txt
_cod_data_source_block           p-1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7108516
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.1958(4) 0.0158(4) 0.0343(3) 0.0303(7) Uani 1 1 d .
C2 C 0.2373(4) 0.1730(4) 0.0201(3) 0.0291(7) Uani 1 1 d .
C3 C 0.2196(4) 0.2267(4) -0.0878(3) 0.0406(8) Uani 1 1 d .
H3 H 0.1816 0.1612 -0.1666 0.049 Uiso 1 1 calc R
C4 C 0.2598(5) 0.3792(5) -0.0741(3) 0.0468(9) Uani 1 1 d .
H4 H 0.2490 0.4185 -0.1448 0.056 Uiso 1 1 calc R
C5 C 0.3163(4) 0.4756(4) 0.0431(3) 0.0438(9) Uani 1 1 d .
H5 H 0.3428 0.5789 0.0499 0.053 Uiso 1 1 calc R
C6 C 0.3346(4) 0.4227(4) 0.1507(3) 0.0359(8) Uani 1 1 d .
H6 H 0.3732 0.4885 0.2294 0.043 Uiso 1 1 calc R
C7 C 0.2934(4) 0.2688(4) 0.1370(3) 0.0270(7) Uani 1 1 d .
C8 C 0.2931(4) 0.1755(3) 0.2341(3) 0.0271(7) Uani 1 1 d .
C9 C 0.1992(4) 0.1818(3) 0.3427(3) 0.0260(6) Uani 1 1 d .
C10 C 0.0437(4) 0.1603(4) 0.3405(3) 0.0316(7) Uani 1 1 d .
H10 H -0.0215 0.1374 0.2643 0.038 Uiso 1 1 calc R
C11 C -0.0146(4) 0.1732(4) 0.4545(3) 0.0354(8) Uani 1 1 d .
H11 H -0.1209 0.1564 0.4551 0.043 Uiso 1 1 calc R
C12 C 0.0847(4) 0.2110(4) 0.5671(3) 0.0359(8) Uani 1 1 d .
H12 H 0.0440 0.2191 0.6428 0.043 Uiso 1 1 calc R
C13 C 0.2433(4) 0.2369(4) 0.5696(3) 0.0332(7) Uani 1 1 d .
H13 H 0.3102 0.2646 0.6460 0.040 Uiso 1 1 calc R
C14 C 0.3003(4) 0.2208(3) 0.4561(3) 0.0258(6) Uani 1 1 d .
C15 C 0.4623(4) 0.2419(3) 0.4294(3) 0.0255(6) Uani 1 1 d .
C16 C 0.4583(4) 0.2172(3) 0.3038(3) 0.0283(7) Uani 1 1 d .
C17 C 0.5956(4) 0.2791(3) 0.5300(3) 0.0279(7) Uani 1 1 d .
C18 C 0.5677(4) 0.1876(4) 0.6205(3) 0.0380(8) Uani 1 1 d .
H18 H 0.4658 0.1019 0.6165 0.046 Uiso 1 1 calc R
C19 C 0.6900(5) 0.2230(5) 0.7160(3) 0.0487(10) Uani 1 1 d .
H19 H 0.6710 0.1602 0.7755 0.058 Uiso 1 1 calc R
C20 C 0.8392(5) 0.3500(5) 0.7240(3) 0.0503(10) Uani 1 1 d .
H20 H 0.9208 0.3745 0.7897 0.060 Uiso 1 1 calc R
C21 C 0.8691(4) 0.4413(5) 0.6356(3) 0.0455(9) Uani 1 1 d .
H21 H 0.9712 0.5272 0.6408 0.055 Uiso 1 1 calc R
C22 C 0.7476(4) 0.4061(4) 0.5386(3) 0.0351(8) Uani 1 1 d .
H22 H 0.7685 0.4683 0.4786 0.042 Uiso 1 1 calc R
I1 I 0.63468(3) 0.20511(3) 0.20211(2) 0.04340(9) Uani 1 1 d .
O1 O 0.1464(3) -0.1017(3) -0.0421(2) 0.0440(6) Uani 1 1 d .
O2 O 0.2213(3) 0.0178(2) 0.16056(18) 0.0309(5) 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'
I I -0.4742 1.8119 '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 O2 121.0(3)
O1 C1 C2 131.4(3)
O2 C1 C2 107.7(2)
C7 C2 C3 121.6(3)
C7 C2 C1 109.0(3)
C3 C2 C1 129.3(3)
C4 C3 C2 117.6(3)
C4 C3 H3 121.2
C2 C3 H3 121.2
C3 C4 C5 120.8(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 121.7(3)
C4 C5 H5 119.1
C6 C5 H5 119.1
C7 C6 C5 117.5(3)
C7 C6 H6 121.3
C5 C6 H6 121.3
C2 C7 C6 120.8(3)
C2 C7 C8 108.7(3)
C6 C7 C8 130.5(3)
O2 C8 C7 103.4(2)
O2 C8 C9 110.7(2)
C7 C8 C9 115.9(2)
O2 C8 C16 108.5(2)
C7 C8 C16 116.7(3)
C9 C8 C16 101.7(2)
C10 C9 C14 121.5(3)
C10 C9 C8 129.6(3)
C14 C9 C8 108.8(3)
C9 C10 C11 118.5(3)
C9 C10 H10 120.7
C11 C10 H10 120.7
C12 C11 C10 120.2(3)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 121.4(3)
C11 C12 H12 119.3
C13 C12 H12 119.3
C14 C13 C12 118.5(3)
C14 C13 H13 120.8
C12 C13 H13 120.8
C13 C14 C9 119.9(3)
C13 C14 C15 130.6(3)
C9 C14 C15 109.5(2)
C16 C15 C17 129.5(3)
C16 C15 C14 107.7(3)
C17 C15 C14 122.7(2)
C15 C16 C8 112.3(3)
C15 C16 I1 127.8(2)
C8 C16 I1 119.4(2)
C22 C17 C18 118.6(3)
C22 C17 C15 121.5(3)
C18 C17 C15 119.9(3)
C19 C18 C17 120.4(3)
C19 C18 H18 119.8
C17 C18 H18 119.8
C20 C19 C18 120.3(4)
C20 C19 H19 119.9
C18 C19 H19 119.9
C19 C20 C21 120.2(3)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C22 120.0(4)
C20 C21 H21 120.0
C22 C21 H21 120.0
C17 C22 C21 120.5(3)
C17 C22 H22 119.7
C21 C22 H22 119.7
C1 O2 C8 110.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.198(4)
C1 O2 1.369(3)
C1 C2 1.463(5)
C2 C7 1.374(4)
C2 C3 1.387(4)
C3 C4 1.367(5)
C3 H3 0.9300
C4 C5 1.379(5)
C4 H4 0.9300
C5 C6 1.380(5)
C5 H5 0.9300
C6 C7 1.378(4)
C6 H6 0.9300
C7 C8 1.502(4)
C8 O2 1.462(3)
C8 C9 1.517(4)
C8 C16 1.522(4)
C9 C10 1.367(4)
C9 C14 1.394(4)
C10 C11 1.388(4)
C10 H10 0.9300
C11 C12 1.379(5)
C11 H11 0.9300
C12 C13 1.382(4)
C12 H12 0.9300
C13 C14 1.382(4)
C13 H13 0.9300
C14 C15 1.482(4)
C15 C16 1.340(4)
C15 C17 1.477(4)
C16 I1 2.073(3)
C17 C22 1.380(4)
C17 C18 1.389(4)
C18 C19 1.375(5)
C18 H18 0.9300
C19 C20 1.365(6)
C19 H19 0.9300
C20 C21 1.367(5)
C20 H20 0.9300
C21 C22 1.381(5)
C21 H21 0.9300
C22 H22 0.9300
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
O1 C1 C2 C7 -178.3(3)
O2 C1 C2 C7 2.4(3)
O1 C1 C2 C3 5.0(6)
O2 C1 C2 C3 -174.4(3)
C7 C2 C3 C4 0.0(5)
C1 C2 C3 C4 176.4(3)
C2 C3 C4 C5 0.1(5)
C3 C4 C5 C6 0.1(6)
C4 C5 C6 C7 -0.3(5)
C3 C2 C7 C6 -0.3(5)
C1 C2 C7 C6 -177.3(3)
C3 C2 C7 C8 178.0(3)
C1 C2 C7 C8 1.0(3)
C5 C6 C7 C2 0.4(5)
C5 C6 C7 C8 -177.4(3)
C2 C7 C8 O2 -3.7(3)
C6 C7 C8 O2 174.3(3)
C2 C7 C8 C9 -125.0(3)
C6 C7 C8 C9 53.0(4)
C2 C7 C8 C16 115.3(3)
C6 C7 C8 C16 -66.6(4)
O2 C8 C9 C10 -67.4(4)
C7 C8 C9 C10 49.9(4)
C16 C8 C9 C10 177.5(3)
O2 C8 C9 C14 114.7(3)
C7 C8 C9 C14 -128.0(3)
C16 C8 C9 C14 -0.4(3)
C14 C9 C10 C11 -2.0(5)
C8 C9 C10 C11 -179.7(3)
C9 C10 C11 C12 1.6(5)
C10 C11 C12 C13 0.1(5)
C11 C12 C13 C14 -1.5(5)
C12 C13 C14 C9 1.1(5)
C12 C13 C14 C15 179.5(3)
C10 C9 C14 C13 0.6(5)
C8 C9 C14 C13 178.7(3)
C10 C9 C14 C15 -178.1(3)
C8 C9 C14 C15 0.1(3)
C13 C14 C15 C16 -178.1(3)
C9 C14 C15 C16 0.4(3)
C13 C14 C15 C17 3.4(5)
C9 C14 C15 C17 -178.1(3)
C17 C15 C16 C8 177.7(3)
C14 C15 C16 C8 -0.7(3)
C17 C15 C16 I1 5.4(5)
C14 C15 C16 I1 -173.0(2)
O2 C8 C16 C15 -116.0(3)
C7 C8 C16 C15 127.7(3)
C9 C8 C16 C15 0.7(3)
O2 C8 C16 I1 57.0(3)
C7 C8 C16 I1 -59.2(3)
C9 C8 C16 I1 173.70(19)
C16 C15 C17 C22 56.5(5)
C14 C15 C17 C22 -125.5(3)
C16 C15 C17 C18 -125.2(4)
C14 C15 C17 C18 52.9(4)
C22 C17 C18 C19 -0.3(5)
C15 C17 C18 C19 -178.7(3)
C17 C18 C19 C20 1.1(5)
C18 C19 C20 C21 -1.2(5)
C19 C20 C21 C22 0.6(5)
C18 C17 C22 C21 -0.3(5)
C15 C17 C22 C21 178.1(3)
C20 C21 C22 C17 0.1(5)
O1 C1 O2 C8 175.7(3)
C2 C1 O2 C8 -4.9(3)
C7 C8 O2 C1 5.3(3)
C9 C8 O2 C1 130.1(2)
C16 C8 O2 C1 -119.2(3)
