#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:11:10 +0200 (mar 06 de oct de 2020) $
#$Revision: 257961 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/03/7240398.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_7240398
loop_
_publ_author_name
'Al-Zoubi, Raed M.'
'Al-Omari, Mothana K.'
'Al-Jammal, Walid K.'
'Ferguson, Michael J.'
_publ_section_title
;
 Palladium-catalyzed highly regioselective mono and double Sonogashira
 cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under
 ambient conditions
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              16366
_journal_page_last               16376
_journal_paper_doi               10.1039/D0RA01569E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C24 H10 Cl F6 I'
_chemical_formula_sum            'C24 H10 Cl F6 I'
_chemical_formula_weight         574.67
_chemical_name_systematic
;
5-chloro-2-iodo-1,3-bis{[4-trifluoromethyl)phenyl]ethynyl}benzene
;
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-05 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                91.3034(15)
_cell_angle_beta                 91.6389(14)
_cell_angle_gamma                111.5614(14)
_cell_formula_units_Z            2
_cell_length_a                   9.8013(12)
_cell_length_b                   10.0715(12)
_cell_length_c                   11.7314(14)
_cell_measurement_reflns_used    4048
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.24
_cell_volume                     1075.9(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.990
_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  0.0189
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.590
_diffrn_reflns_theta_min         1.738
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  0.9260
_exptl_absorpt_correction_T_min  0.7647
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       fragment
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.8785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3710
_reflns_number_total             4456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01569e2.cif
_cod_data_source_block           jus1803
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_database_code               7240398
_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   0.689
_shelx_estimated_absorpt_t_max   0.847
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 0.33158(3) 0.65115(3) 0.25399(2) 0.05633(12) Uani 1 1 d . . . . .
Cl1 Cl -0.05318(11) 1.06507(11) 0.22057(9) 0.0539(2) Uani 1 1 d . . . . .
F1 F 0.5486(3) 0.6717(3) 0.9926(2) 0.0763(8) Uani 1 1 d . . . . .
F2 F 0.7593(3) 0.7694(3) 0.9250(2) 0.0725(8) Uani 1 1 d . . . . .
F3 F 0.6677(4) 0.8953(3) 1.0176(2) 0.0873(9) Uani 1 1 d . . . . .
F4 F 0.3254(3) 0.4116(3) -0.4972(2) 0.0807(9) Uani 1 1 d . . . . .
F5 F 0.0952(4) 0.2966(4) -0.5169(2) 0.0882(10) Uani 1 1 d . . . . .
F6 F 0.2262(4) 0.2104(3) -0.4207(2) 0.0779(8) Uani 1 1 d . . . . .
C1 C 0.2036(3) 0.8656(3) 0.3393(2) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.2122(3) 0.7838(3) 0.2430(3) 0.0312(6) Uani 1 1 d . . . . .
C3 C 0.1407(3) 0.7911(3) 0.1396(3) 0.0305(6) Uani 1 1 d . . . . .
C4 C 0.0584(4) 0.8793(3) 0.1342(3) 0.0343(7) Uani 1 1 d . . . . .
H4 H 0.007930 0.884074 0.065037 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0509(3) 0.9585(3) 0.2289(3) 0.0344(7) Uani 1 1 d . . . . .
C6 C 0.1221(4) 0.9533(3) 0.3312(3) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.115507 1.009177 0.395615 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2776(4) 0.8607(4) 0.4458(3) 0.0362(7) Uani 1 1 d . . . . .
C8 C 0.3399(4) 0.8579(4) 0.5336(3) 0.0375(7) Uani 1 1 d . . . . .
C9 C 0.1482(4) 0.7110(3) 0.0388(3) 0.0353(7) Uani 1 1 d . . . . .
C10 C 0.1524(4) 0.6458(4) -0.0463(3) 0.0362(7) Uani 1 1 d . . . . .
C11 C 0.4184(3) 0.8468(3) 0.6363(3) 0.0326(7) Uani 1 1 d . . . . .
C12 C 0.4207(4) 0.9265(4) 0.7354(3) 0.0374(7) Uani 1 1 d . . . . .
H12 H 0.372872 0.993197 0.735534 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4924(4) 0.9085(4) 0.8334(3) 0.0396(8) Uani 1 1 d . . . . .
H13 H 0.493120 0.962492 0.901033 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5628(4) 0.8131(4) 0.8339(3) 0.0355(7) Uani 1 1 d . . . . .
C15 C 0.5640(4) 0.7352(4) 0.7357(3) 0.0423(8) Uani 1 1 d . . . . .
H15 H 0.614870 0.670985 0.735828 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4911(4) 0.7508(4) 0.6370(3) 0.0400(8) Uani 1 1 d . . . . .
H16 H 0.490584 0.696131 0.569793 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6337(4) 0.7873(4) 0.9416(3) 0.0482(9) Uani 1 1 d . . . . .
C21 C 0.1617(3) 0.5636(3) -0.1454(3) 0.0319(7) Uani 1 1 d . . . . .
C22 C 0.1010(4) 0.5789(4) -0.2505(3) 0.0416(8) Uani 1 1 d . . . . .
H22 H 0.050579 0.642960 -0.257173 0.050 Uiso 1 1 calc R U . . .
C23 C 0.1140(4) 0.5010(4) -0.3453(3) 0.0448(9) Uani 1 1 d . . . . .
H23 H 0.072076 0.511694 -0.416921 0.054 Uiso 1 1 calc R U . . .
C24 C 0.1870(4) 0.4081(4) -0.3368(3) 0.0368(7) Uani 1 1 d . . . . .
C25 C 0.2470(4) 0.3908(4) -0.2331(3) 0.0416(8) Uani 1 1 d . . . . .
H25 H 0.296429 0.325840 -0.226874 0.050 Uiso 1 1 calc R U . . .
C26 C 0.2345(4) 0.4694(4) -0.1375(3) 0.0394(8) Uani 1 1 d . . . . .
H26 H 0.276421 0.458271 -0.066027 0.047 Uiso 1 1 calc R U . . .
C27 C 0.2082(5) 0.3316(4) -0.4419(3) 0.0514(10) 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'
F F 0.0171 0.0103 '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
C6 C1 C2 119.3(3) . . ?
C6 C1 C7 119.5(3) . . ?
C2 C1 C7 121.2(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 I1 119.8(2) . . ?
C1 C2 I1 119.9(2) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 C9 122.3(3) . . ?
C4 C3 C9 118.7(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 Cl1 119.2(2) . . ?
C6 C5 Cl1 119.3(2) . . ?
C5 C6 C1 119.7(3) . . ?
C8 C7 C1 179.3(4) . . ?
C7 C8 C11 175.9(4) . . ?
C10 C9 C3 178.5(4) . . ?
C9 C10 C21 177.0(4) . . ?
C12 C11 C16 119.3(3) . . ?
C12 C11 C8 121.8(3) . . ?
C16 C11 C8 118.9(3) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 120.5(3) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 C17 120.7(3) . . ?
C15 C14 C17 119.0(3) . . ?
C14 C15 C16 119.9(3) . . ?
C15 C16 C11 120.0(3) . . ?
F1 C17 F2 106.2(3) . . ?
F1 C17 F3 106.8(3) . . ?
F2 C17 F3 104.9(3) . . ?
F1 C17 C14 112.2(3) . . ?
F2 C17 C14 113.2(3) . . ?
F3 C17 C14 112.9(3) . . ?
C26 C21 C22 119.0(3) . . ?
C26 C21 C10 119.9(3) . . ?
C22 C21 C10 121.1(3) . . ?
C23 C22 C21 120.1(3) . . ?
C24 C23 C22 120.5(3) . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 C27 119.7(3) . . ?
C25 C24 C27 120.1(3) . . ?
C24 C25 C26 119.5(3) . . ?
C21 C26 C25 120.7(3) . . ?
F6 C27 F5 105.5(3) . . ?
F6 C27 F4 106.7(3) . . ?
F5 C27 F4 106.1(4) . . ?
F6 C27 C24 113.4(3) . . ?
F5 C27 C24 113.0(3) . . ?
F4 C27 C24 111.6(3) . . ?
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 C2 2.078(3) . ?
Cl1 C5 1.734(3) . ?
F1 C17 1.325(5) . ?
F2 C17 1.327(5) . ?
F3 C17 1.327(5) . ?
F4 C27 1.332(5) . ?
F5 C27 1.330(5) . ?
F6 C27 1.323(5) . ?
C1 C6 1.395(5) . ?
C1 C2 1.406(4) . ?
C1 C7 1.437(4) . ?
C2 C3 1.400(4) . ?
C3 C4 1.403(4) . ?
C3 C9 1.435(4) . ?
C4 C5 1.372(4) . ?
C5 C6 1.383(5) . ?
C7 C8 1.189(5) . ?
C8 C11 1.439(4) . ?
C9 C10 1.193(4) . ?
C10 C21 1.436(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.396(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.373(5) . ?
C14 C15 1.382(5) . ?
C14 C17 1.499(5) . ?
C15 C16 1.385(5) . ?
C21 C26 1.383(5) . ?
C21 C22 1.390(5) . ?
C22 C23 1.382(5) . ?
C23 C24 1.375(5) . ?
C24 C25 1.379(5) . ?
C24 C27 1.499(5) . ?
C25 C26 1.392(5) . ?
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
C6 C1 C2 C3 0.5(5) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C6 C1 C2 I1 -179.5(2) . . . . ?
C7 C1 C2 I1 0.7(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
I1 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C9 179.1(3) . . . . ?
I1 C2 C3 C9 -0.9(4) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C9 C3 C4 C5 -179.1(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 Cl1 -179.2(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
Cl1 C5 C6 C1 178.7(2) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C16 C11 C12 C13 -1.0(5) . . . . ?
C8 C11 C12 C13 177.4(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C12 C13 C14 C17 -176.6(3) . . . . ?
C13 C14 C15 C16 -1.5(5) . . . . ?
C17 C14 C15 C16 175.9(3) . . . . ?
C14 C15 C16 C11 1.0(5) . . . . ?
C12 C11 C16 C15 0.2(5) . . . . ?
C8 C11 C16 C15 -178.2(3) . . . . ?
C13 C14 C17 F1 97.8(4) . . . . ?
C15 C14 C17 F1 -79.7(5) . . . . ?
C13 C14 C17 F2 -142.0(4) . . . . ?
C15 C14 C17 F2 40.6(5) . . . . ?
C13 C14 C17 F3 -23.0(5) . . . . ?
C15 C14 C17 F3 159.5(4) . . . . ?
C26 C21 C22 C23 -0.1(5) . . . . ?
C10 C21 C22 C23 178.6(3) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C23 C24 C25 0.6(6) . . . . ?
C22 C23 C24 C27 -176.1(4) . . . . ?
C23 C24 C25 C26 -0.8(5) . . . . ?
C27 C24 C25 C26 175.9(3) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
C10 C21 C26 C25 -178.8(3) . . . . ?
C24 C25 C26 C21 0.5(5) . . . . ?
C23 C24 C27 F6 -155.4(4) . . . . ?
C25 C24 C27 F6 27.9(5) . . . . ?
C23 C24 C27 F5 -35.4(5) . . . . ?
C25 C24 C27 F5 147.9(4) . . . . ?
C23 C24 C27 F4 84.0(5) . . . . ?
C25 C24 C27 F4 -92.7(4) . . . . ?
