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#$Date: 2020-10-06 14:11:10 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257961 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240400.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_7240400
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         'C15 H6 Cl F3 I2'
_chemical_formula_sum            'C15 H6 Cl F3 I2'
_chemical_formula_weight         532.45
_chemical_name_systematic
;
5-chloro-1,2-diiodo-3-{[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                72.6614(8)
_cell_angle_beta                 71.6046(7)
_cell_angle_gamma                64.6041(7)
_cell_formula_units_Z            2
_cell_length_a                   8.4281(5)
_cell_length_b                   9.5746(5)
_cell_length_c                   11.4227(6)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.40
_cell_volume                     775.78(7)
_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      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0091
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9508
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.631
_diffrn_reflns_theta_min         1.914
_exptl_absorpt_coefficient_mu    4.246
_exptl_absorpt_correction_T_max  0.4694
_exptl_absorpt_correction_T_min  0.3060
_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    2.279
_exptl_crystal_description       fragment
_exptl_crystal_F_000             492
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes/dichloromethane'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.071
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0180
_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)+(0.0165P)²+0.6203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0414
_refine_ls_wR_factor_ref         0.0426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4325
_reflns_number_total             4763
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01569e2.cif
_cod_data_source_block           jus1810
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_database_code               7240400
_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   0.462
_shelx_estimated_absorpt_t_max   0.753
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 0.44908(2) 0.08527(2) 0.14714(2) 0.03707(4) Uani 1 1 d . . . . .
I2 I 0.25724(2) 0.37122(2) 0.35374(2) 0.03377(4) Uani 1 1 d . . . . .
Cl1 Cl 1.05747(6) -0.19302(6) 0.36331(5) 0.03706(11) Uani 1 1 d . . . . .
F1A F 0.1791(3) 0.7698(3) 1.0301(2) 0.0708(8) Uani 0.912(5) 1 d . . P A 1
F2A F -0.0121(4) 0.6629(3) 1.0946(2) 0.0831(11) Uani 0.912(5) 1 d . . P A 1
F3A F -0.0486(4) 0.8712(2) 0.9507(2) 0.0779(8) Uani 0.912(5) 1 d . . P A 1
F1B F 0.137(3) 0.695(2) 1.0837(19) 0.055(5) Uiso 0.088(5) 1 d . . P A 2
F2B F -0.096(2) 0.7246(18) 1.0398(15) 0.034(4) Uiso 0.088(5) 1 d . . P A 2
F3B F 0.030(2) 0.8685(19) 0.9569(15) 0.032(4) Uiso 0.088(5) 1 d . . P A 2
C1 C 0.5799(2) 0.07908(19) 0.27788(15) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.5027(2) 0.18285(18) 0.36200(15) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.5946(2) 0.16239(18) 0.45313(15) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.7641(2) 0.0427(2) 0.45541(16) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.825829 0.026761 0.517786 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8414(2) -0.05230(19) 0.36643(16) 0.0245(3) Uani 1 1 d . . . . .
C6 C 0.7502(2) -0.0383(2) 0.27907(16) 0.0260(3) Uani 1 1 d . . . . .
H6 H 0.802955 -0.107557 0.220897 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5171(2) 0.2612(2) 0.54510(16) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.4514(2) 0.3407(2) 0.62378(16) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.3587(2) 0.4396(2) 0.71634(16) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.2050(2) 0.5720(2) 0.69627(16) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.164151 0.596713 0.621359 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1113(2) 0.6681(2) 0.78531(17) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.006301 0.758089 0.771689 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1722(3) 0.6318(2) 0.89390(17) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.3244(3) 0.5000(2) 0.91547(18) 0.0343(4) Uani 1 1 d . . . . .
H13 H 0.364075 0.475653 0.990826 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4185(3) 0.4038(2) 0.82681(18) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.523292 0.313854 0.841038 0.038 Uiso 1 1 calc R U . . .
C15 C 0.0718(3) 0.7332(3) 0.9918(2) 0.0380(4) 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 120.80(15) . . ?
C6 C1 I1 116.08(12) . . ?
C2 C1 I1 123.10(12) . . ?
C1 C2 C3 119.20(15) . . ?
C1 C2 I2 121.91(12) . . ?
C3 C2 I2 118.87(11) . . ?
C4 C3 C2 119.74(14) . . ?
C4 C3 C7 119.03(15) . . ?
C2 C3 C7 121.23(15) . . ?
C5 C4 C3 119.64(16) . . ?
C4 C5 C6 121.50(16) . . ?
C4 C5 Cl1 119.64(13) . . ?
C6 C5 Cl1 118.86(13) . . ?
C5 C6 C1 118.95(15) . . ?
C8 C7 C3 178.48(19) . . ?
C7 C8 C9 175.39(19) . . ?
C10 C9 C14 119.64(15) . . ?
C10 C9 C8 119.25(16) . . ?
C14 C9 C8 121.10(16) . . ?
C11 C10 C9 120.33(17) . . ?
C12 C11 C10 119.49(17) . . ?
C11 C12 C13 120.83(16) . . ?
C11 C12 C15 120.32(18) . . ?
C13 C12 C15 118.83(18) . . ?
C12 C13 C14 119.90(17) . . ?
C13 C14 C9 119.80(17) . . ?
F3B C15 F1B 108.8(12) . . ?
F2A C15 F1A 105.2(2) . . ?
F2A C15 F3A 108.1(2) . . ?
F1A C15 F3A 104.9(2) . . ?
F3B C15 F2B 99.5(10) . . ?
F1B C15 F2B 104.9(12) . . ?
F3B C15 C12 116.9(8) . . ?
F1B C15 C12 116.2(9) . . ?
F2A C15 C12 112.55(17) . . ?
F1A C15 C12 112.51(18) . . ?
F3A C15 C12 113.06(19) . . ?
F2B C15 C12 108.5(6) . . ?
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 C1 2.0930(17) . ?
I2 C2 2.0887(16) . ?
Cl1 C5 1.7368(17) . ?
F1A C15 1.321(3) . ?
F2A C15 1.321(3) . ?
F3A C15 1.334(3) . ?
F1B C15 1.226(19) . ?
F2B C15 1.375(15) . ?
F3B C15 1.163(16) . ?
C1 C6 1.394(2) . ?
C1 C2 1.398(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.399(2) . ?
C3 C7 1.433(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.385(2) . ?
C7 C8 1.195(2) . ?
C8 C9 1.437(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.400(3) . ?
C10 C11 1.390(2) . ?
C11 C12 1.383(3) . ?
C12 C13 1.387(3) . ?
C12 C15 1.502(2) . ?
C13 C14 1.388(2) . ?
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 -3.5(3) . . . . ?
I1 C1 C2 C3 175.11(12) . . . . ?
C6 C1 C2 I2 175.00(13) . . . . ?
I1 C1 C2 I2 -6.4(2) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
I2 C2 C3 C4 -176.20(12) . . . . ?
C1 C2 C3 C7 -177.05(16) . . . . ?
I2 C2 C3 C7 4.4(2) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C7 C3 C4 C5 -179.28(16) . . . . ?
C3 C4 C5 C6 -4.0(3) . . . . ?
C3 C4 C5 Cl1 176.10(13) . . . . ?
C4 C5 C6 C1 2.8(3) . . . . ?
Cl1 C5 C6 C1 -177.24(14) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
I1 C1 C6 C5 -177.74(13) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 178.98(17) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C10 C11 C12 C15 -179.38(18) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C15 C12 C13 C14 179.47(19) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 -178.88(19) . . . . ?
C11 C12 C15 F3B -47.4(10) . . . . ?
C13 C12 C15 F3B 133.8(10) . . . . ?
C11 C12 C15 F1B -178.2(13) . . . . ?
C13 C12 C15 F1B 3.0(13) . . . . ?
C11 C12 C15 F2A 109.0(3) . . . . ?
C13 C12 C15 F2A -69.8(3) . . . . ?
C11 C12 C15 F1A -132.4(2) . . . . ?
C13 C12 C15 F1A 48.8(3) . . . . ?
C11 C12 C15 F3A -13.8(3) . . . . ?
C13 C12 C15 F3A 167.4(2) . . . . ?
C11 C12 C15 F2B 64.0(8) . . . . ?
C13 C12 C15 F2B -114.8(8) . . . . ?
