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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/7/24/04/7240401.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_7240401
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 H9 F I2 O'
_chemical_formula_sum            'C15 H9 F I2 O'
_chemical_formula_weight         478.02
_chemical_name_systematic
;
5-fluoro-1,2-diiodo-3-[(4-methoxyphenyl)ethynyl]benzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.15290(8)
_cell_length_b                   11.4859(2)
_cell_length_c                   30.5943(6)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.63
_cell_measurement_theta_min      4.11
_cell_volume                     1459.34(5)
_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 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9797
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    33.866
_exptl_absorpt_correction_T_max  0.1121
_exptl_absorpt_correction_T_min  0.0046
_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    2.176
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes/dichloromethane'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.037(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0149
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0147P)²+0.2798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0379
_refine_ls_wR_factor_ref         0.0380
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2918
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01569e2.cif
_cod_data_source_block           jus1809
_cod_depositor_comments
'Adding full bibliography for 7240398--7240401.cif.'
_cod_original_cell_volume        1459.35(5)
_cod_database_code               7240401
_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   0.075
_shelx_estimated_absorpt_t_max   0.451
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 -0.06974(6) 0.63448(2) 0.52821(2) 0.05149(8) Uani 1 1 d . . . . .
I2 I 0.24743(6) 0.67450(2) 0.63847(2) 0.04729(7) Uani 1 1 d . . . . .
F1 F 0.2990(10) 0.1948(2) 0.54633(8) 0.0723(9) Uani 1 1 d . . . . .
O1 O 1.1160(9) 0.5739(3) 0.87119(9) 0.0561(7) Uani 1 1 d . . . . .
C1 C 0.1469(8) 0.5001(3) 0.56417(11) 0.0401(7) Uani 1 1 d . . . . .
C2 C 0.2755(9) 0.5159(3) 0.60570(10) 0.0385(6) Uani 1 1 d . . . . .
C3 C 0.4262(10) 0.4211(3) 0.62718(10) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.4359(11) 0.3119(3) 0.60624(11) 0.0470(8) Uani 1 1 d . . . . .
H4 H 0.535828 0.246984 0.619904 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2982(12) 0.3013(3) 0.56583(12) 0.0507(9) Uani 1 1 d . . . . .
C6 C 0.1561(10) 0.3915(4) 0.54378(11) 0.0496(9) Uani 1 1 d . . . . .
H6 H 0.066699 0.380400 0.515506 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5640(10) 0.4345(3) 0.66967(11) 0.0414(7) Uani 1 1 d . . . . .
C8 C 0.6764(9) 0.4488(3) 0.70508(11) 0.0426(8) Uani 1 1 d . . . . .
C9 C 0.7992(9) 0.4771(3) 0.74767(11) 0.0409(7) Uani 1 1 d . . . . .
C10 C 0.9692(10) 0.3973(3) 0.77266(11) 0.0436(8) Uani 1 1 d . . . . .
H10 H 1.009023 0.321629 0.761338 0.052 Uiso 1 1 calc R U . . .
C11 C 1.0819(11) 0.4262(3) 0.81398(11) 0.0429(7) Uani 1 1 d . . . . .
H11 H 1.198483 0.370867 0.830762 0.052 Uiso 1 1 calc R U . . .
C12 C 1.0227(10) 0.5374(3) 0.83070(11) 0.0432(8) Uani 1 1 d . . . . .
C13 C 0.8563(10) 0.6189(3) 0.80560(13) 0.0481(9) Uani 1 1 d . . . . .
H13 H 0.819425 0.694991 0.816703 0.058 Uiso 1 1 calc R U . . .
C14 C 0.7451(12) 0.5889(3) 0.76452(11) 0.0450(7) Uani 1 1 d . . . . .
H14 H 0.630933 0.644532 0.747562 0.054 Uiso 1 1 calc R U . . .
C15 C 1.2571(15) 0.4896(4) 0.89985(13) 0.0617(11) Uani 1 1 d . . . . .
H15A H 1.286659 0.524056 0.928881 0.074 Uiso 1 1 calc R U . . .
H15B H 1.466455 0.465302 0.888212 0.074 Uiso 1 1 calc R U . . .
H15C H 1.114923 0.421781 0.902078 0.074 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C12 O1 C15 117.7(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 I1 123.2(3) . . ?
C6 C1 I1 115.8(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 I2 122.2(3) . . ?
C3 C2 I2 118.3(2) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 C7 119.9(3) . . ?
C2 C3 C7 121.1(3) . . ?
C5 C4 C3 118.6(4) . . ?
F1 C5 C4 118.4(4) . . ?
F1 C5 C6 117.7(4) . . ?
C4 C5 C6 123.9(4) . . ?
C5 C6 C1 117.9(3) . . ?
C8 C7 C3 178.2(4) . . ?
C7 C8 C9 174.5(4) . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 C8 122.0(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 121.0(3) . . ?
C10 C11 C12 119.5(4) . . ?
O1 C12 C13 115.7(3) . . ?
O1 C12 C11 124.3(4) . . ?
C13 C12 C11 119.9(3) . . ?
C14 C13 C12 119.9(4) . . ?
C13 C14 C9 120.6(4) . . ?
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 2.098(3) . ?
I2 C2 2.083(3) . ?
F1 C5 1.361(5) . ?
O1 C12 1.364(4) . ?
O1 C15 1.432(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.395(6) . ?
C2 C3 1.418(5) . ?
C3 C4 1.409(5) . ?
C3 C7 1.429(5) . ?
C4 C5 1.368(6) . ?
C5 C6 1.370(6) . ?
C7 C8 1.191(5) . ?
C8 C9 1.437(5) . ?
C9 C10 1.387(5) . ?
C9 C14 1.401(5) . ?
C10 C11 1.388(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.395(6) . ?
C13 C14 1.383(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 1.8(5) . . . . ?
I1 C1 C2 C3 -178.1(3) . . . . ?
C6 C1 C2 I2 -177.1(3) . . . . ?
I1 C1 C2 I2 3.1(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
I2 C2 C3 C4 177.4(3) . . . . ?
C1 C2 C3 C7 179.3(3) . . . . ?
I2 C2 C3 C7 -1.8(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C7 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 F1 -177.9(4) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
F1 C5 C6 C1 178.3(4) . . . . ?
C4 C5 C6 C1 -1.1(7) . . . . ?
C2 C1 C6 C5 -0.5(6) . . . . ?
I1 C1 C6 C5 179.3(3) . . . . ?
C14 C9 C10 C11 0.7(6) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C15 O1 C12 C13 173.6(4) . . . . ?
C15 O1 C12 C11 -6.0(6) . . . . ?
C10 C11 C12 O1 178.4(4) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
O1 C12 C13 C14 -178.4(4) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 C13 -0.7(6) . . . . ?
C8 C9 C14 C13 179.2(4) . . . . ?
