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#$Date: 2021-09-10 04:20:35 +0300 (Fri, 10 Sep 2021) $
#$Revision: 269083 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243501.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_7243501
loop_
_publ_author_name
'Al-Zoubi, Raed M.'
'Al-Jammal, Walid K.'
'Ferguson, Michael J.'
'Murphy, Graham K.'
_publ_section_title
;
 Domino C--C/C--O bond formation: palladium-catalyzed regioselective
 synthesis of 7-iodobenzo[b]furans using 1,2,3-triiodobenzenes and
 benzylketones
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              30069
_journal_page_last               30077
_journal_paper_doi               10.1039/D1RA05730H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H12 Cl I O'
_chemical_formula_sum            'C20 H12 Cl I O'
_chemical_formula_weight         430.65
_chemical_name_systematic        2-(4-chlorophenyl)-7-iodo-3-phenyl-1-benzofuran
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-11-30 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                86.607(3)
_cell_angle_beta                 65.448(3)
_cell_angle_gamma                70.670(3)
_cell_formula_units_Z            2
_cell_length_a                   9.244(2)
_cell_length_b                   9.988(3)
_cell_length_c                   10.515(3)
_cell_measurement_reflns_used    6231
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.17
_cell_volume                     829.8(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-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.634
_diffrn_reflns_theta_min         2.138
_exptl_absorpt_coefficient_mu    2.092
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_correction_T_min  0.7307
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0329P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3365
_reflns_number_total             3843
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra05730h2.cif
_cod_data_source_block           jus1802
_cod_database_code               7243501
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.639
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.79344(2) -0.01350(2) 0.34954(2) 0.04862(8) Uani 1 1 d . . . . .
Cl1 Cl -0.27026(7) 0.67509(6) 0.82007(6) 0.03918(14) Uani 1 1 d . . . . .
O1 O 0.52940(19) 0.31735(15) 0.37816(16) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.4391(3) 0.4592(2) 0.3730(2) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.5323(3) 0.5162(2) 0.2616(2) 0.0274(4) Uani 1 1 d . . . . .
C3 C 0.6931(3) 0.4057(2) 0.1897(2) 0.0275(4) Uani 1 1 d . . . . .
C4 C 0.8424(3) 0.3965(3) 0.0697(2) 0.0330(5) Uani 1 1 d . . . . .
H4 H 0.852628 0.476011 0.016856 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9737(3) 0.2671(3) 0.0317(3) 0.0368(5) Uani 1 1 d . . . . .
H5 H 1.075609 0.258576 -0.048673 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9607(3) 0.1487(3) 0.1081(3) 0.0360(5) Uani 1 1 d . . . . .
H6 H 1.053036 0.061524 0.078350 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8149(3) 0.1571(2) 0.2265(2) 0.0326(5) Uani 1 1 d . . . . .
C8 C 0.6826(3) 0.2866(2) 0.2648(2) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.2664(3) 0.5130(2) 0.4836(2) 0.0271(4) Uani 1 1 d . . . . .
C10 C 0.1913(3) 0.4185(2) 0.5657(2) 0.0300(4) Uani 1 1 d . . . . .
H10 H 0.253679 0.319351 0.550268 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0271(3) 0.4674(2) 0.6693(2) 0.0324(5) Uani 1 1 d . . . . .
H11 H -0.022786 0.402387 0.724557 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0633(3) 0.6122(2) 0.6910(2) 0.0301(4) Uani 1 1 d . . . . .
C13 C 0.0079(3) 0.7085(2) 0.6113(2) 0.0311(5) Uani 1 1 d . . . . .
H13 H -0.055278 0.807474 0.627120 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1720(3) 0.6590(2) 0.5086(2) 0.0304(5) Uani 1 1 d . . . . .
H14 H 0.221265 0.724729 0.454201 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4773(3) 0.6594(2) 0.2136(2) 0.0267(4) Uani 1 1 d . . . . .
C16 C 0.3862(3) 0.6816(2) 0.1326(2) 0.0311(5) Uani 1 1 d . . . . .
H16 H 0.361866 0.604755 0.106810 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3306(3) 0.8156(2) 0.0891(3) 0.0350(5) Uani 1 1 d . . . . .
H17 H 0.268378 0.829803 0.033845 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3652(3) 0.9283(2) 0.1257(3) 0.0372(5) Uani 1 1 d . . . . .
H18 H 0.326260 1.019935 0.096522 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4568(4) 0.9065(3) 0.2050(3) 0.0427(6) Uani 1 1 d . . . . .
H19 H 0.480702 0.983730 0.230433 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5144(3) 0.7729(3) 0.2481(3) 0.0386(5) Uani 1 1 d . . . . .
H20 H 0.579176 0.758781 0.301169 0.046 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C1 105.83(16) . . ?
C2 C1 O1 111.13(18) . . ?
C2 C1 C9 133.95(19) . . ?
O1 C1 C9 114.90(18) . . ?
C1 C2 C3 106.62(18) . . ?
C1 C2 C15 127.57(19) . . ?
C3 C2 C15 125.60(19) . . ?
C8 C3 C4 119.6(2) . . ?
C8 C3 C2 105.60(19) . . ?
C4 C3 C2 134.8(2) . . ?
C5 C4 C3 117.6(2) . . ?
C4 C5 C6 122.0(2) . . ?
C7 C6 C5 120.8(2) . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 I1 122.23(17) . . ?
C8 C7 I1 120.32(17) . . ?
O1 C8 C7 126.6(2) . . ?
O1 C8 C3 110.80(18) . . ?
C7 C8 C3 122.6(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C1 120.22(19) . . ?
C14 C9 C1 121.30(19) . . ?
C11 C10 C9 121.0(2) . . ?
C12 C11 C10 119.2(2) . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 Cl1 119.73(17) . . ?
C13 C12 Cl1 119.20(17) . . ?
C14 C13 C12 119.4(2) . . ?
C13 C14 C9 120.9(2) . . ?
C16 C15 C20 118.9(2) . . ?
C16 C15 C2 119.56(19) . . ?
C20 C15 C2 121.5(2) . . ?
C17 C16 C15 120.4(2) . . ?
C18 C17 C16 120.5(2) . . ?
C19 C18 C17 119.4(2) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C15 120.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.090(2) . ?
Cl1 C12 1.744(2) . ?
O1 C8 1.369(3) . ?
O1 C1 1.397(2) . ?
C1 C2 1.359(3) . ?
C1 C9 1.467(3) . ?
C2 C3 1.442(3) . ?
C2 C15 1.485(3) . ?
C3 C8 1.397(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.400(4) . ?
C6 C7 1.384(3) . ?
C7 C8 1.391(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.403(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.384(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.394(3) . ?
C16 C17 1.390(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.379(4) . ?
C19 C20 1.389(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C1 C2 -0.6(2) . . . . ?
C8 O1 C1 C9 177.81(17) . . . . ?
O1 C1 C2 C3 -0.1(2) . . . . ?
C9 C1 C2 C3 -178.2(2) . . . . ?
O1 C1 C2 C15 174.78(19) . . . . ?
C9 C1 C2 C15 -3.3(4) . . . . ?
C1 C2 C3 C8 0.8(2) . . . . ?
C15 C2 C3 C8 -174.21(19) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C15 C2 C3 C4 5.2(4) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 I1 -177.03(17) . . . . ?
C1 O1 C8 C7 -179.9(2) . . . . ?
C1 O1 C8 C3 1.2(2) . . . . ?
C6 C7 C8 O1 -179.41(19) . . . . ?
I1 C7 C8 O1 -1.6(3) . . . . ?
C6 C7 C8 C3 -0.6(3) . . . . ?
I1 C7 C8 C3 177.24(15) . . . . ?
C4 C3 C8 O1 179.21(18) . . . . ?
C2 C3 C8 O1 -1.2(2) . . . . ?
C4 C3 C8 C7 0.2(3) . . . . ?
C2 C3 C8 C7 179.8(2) . . . . ?
C2 C1 C9 C10 164.8(2) . . . . ?
O1 C1 C9 C10 -13.2(3) . . . . ?
C2 C1 C9 C14 -14.2(4) . . . . ?
O1 C1 C9 C14 167.77(18) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C1 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C10 C11 C12 Cl1 179.61(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
Cl1 C12 C13 C14 -179.83(17) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C1 C9 C14 C13 178.7(2) . . . . ?
C1 C2 C15 C16 -81.0(3) . . . . ?
C3 C2 C15 C16 93.0(3) . . . . ?
C1 C2 C15 C20 98.9(3) . . . . ?
C3 C2 C15 C20 -87.1(3) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
C2 C15 C16 C17 178.7(2) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C15 -1.2(4) . . . . ?
C16 C15 C20 C19 1.7(4) . . . . ?
C2 C15 C20 C19 -178.1(2) . . . . ?
