#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/29/7122913.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_7122913
loop_
_publ_author_name
'Carreras, Lucas'
'Benet-Buchholz, Jordi'
'Franconetti, Antonio'
'Frontera, Antonio'
'van Leeuwen, Piet W.N.M.'
'Vidal-Ferran, Anton'
_publ_section_title
;
 Halogen Bonding Effects on the Outcome of Reactions at Metal Centres
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08884E
_journal_year                    2019
_chemical_formula_sum            'C18 H10 F4 I P'
_chemical_formula_weight         460.13
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-22 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.274(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.720(3)
_cell_length_b                   6.2838(9)
_cell_length_c                   25.272(4)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.94
_cell_measurement_theta_min      2.88
_cell_volume                     3327.4(8)
_computing_cell_refinement       'Bruker APEX3 v2015.9-0'
_computing_data_collection       'Bruker APEX3 v2015.9-0'
_computing_data_reduction        'Bruker SAINT V8.35A'
_computing_molecular_graphics
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'XCIF, SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT V2014/4 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            35362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.996
_diffrn_reflns_theta_min         2.204
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0095P)²+7.2161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6648
_reflns_number_total             6986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc08884e2.cif
_cod_data_source_block           mo_LCAR299_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7122913
_shelx_shelxl_version_number     2014/7
_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   0.748
_shelx_estimated_absorpt_t_max   0.922
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
P1 P 0.58504(2) 0.56829(6) 0.13782(2) 0.01228(6) Uani 1 1 d . .
I1 I 0.44688(2) 0.35899(2) 0.04997(2) 0.01689(3) Uani 1 1 d . .
C1 C 0.50895(6) 0.7051(2) 0.13491(5) 0.0127(2) Uani 1 1 d . .
C2 C 0.45135(6) 0.6237(2) 0.10106(5) 0.0125(2) Uani 1 1 d . .
C3 C 0.39365(6) 0.7242(2) 0.09807(6) 0.0152(2) Uani 1 1 d . .
C4 C 0.39083(7) 0.9066(2) 0.12791(6) 0.0173(2) Uani 1 1 d . .
C5 C 0.44629(7) 0.9885(2) 0.16171(6) 0.0178(2) Uani 1 1 d . .
C6 C 0.50399(7) 0.8884(2) 0.16460(6) 0.0166(2) Uani 1 1 d . .
C7 C 0.63378(6) 0.6147(2) 0.20810(5) 0.0119(2) Uani 1 1 d . .
C8 C 0.67729(7) 0.7823(2) 0.22336(6) 0.0149(2) Uani 1 1 d . .
H8 H 0.6801 0.8879 0.1972 0.018 Uiso 1 1 calc R U
C9 C 0.71659(7) 0.7956(2) 0.27660(6) 0.0166(2) Uani 1 1 d . .
H9 H 0.7460 0.9098 0.2866 0.020 Uiso 1 1 calc R U
C10 C 0.71278(7) 0.6418(3) 0.31523(6) 0.0178(2) Uani 1 1 d . .
H10 H 0.7399 0.6501 0.3514 0.021 Uiso 1 1 calc R U
C11 C 0.66919(8) 0.4759(3) 0.30068(6) 0.0199(3) Uani 1 1 d . .
H11 H 0.6659 0.3723 0.3272 0.024 Uiso 1 1 calc R U
C12 C 0.63016(7) 0.4614(2) 0.24715(6) 0.0166(2) Uani 1 1 d . .
H12 H 0.6010 0.3465 0.2373 0.020 Uiso 1 1 calc R U
C13 C 0.62220(6) 0.7498(2) 0.09850(5) 0.0133(2) Uani 1 1 d . .
C14 C 0.68009(7) 0.6811(2) 0.08957(6) 0.0168(2) Uani 1 1 d . .
H14 H 0.6976 0.5482 0.1040 0.020 Uiso 1 1 calc R U
C15 C 0.71201(7) 0.8048(3) 0.05992(6) 0.0201(3) Uani 1 1 d . .
H15 H 0.7516 0.7574 0.0548 0.024 Uiso 1 1 calc R U
C16 C 0.68636(7) 0.9984(3) 0.03758(6) 0.0199(3) Uani 1 1 d . .
H16 H 0.7081 1.0824 0.0169 0.024 Uiso 1 1 calc R U
C17 C 0.62872(8) 1.0677(3) 0.04576(6) 0.0205(3) Uani 1 1 d . .
H17 H 0.6109 1.1992 0.0305 0.025 Uiso 1 1 calc R U
C18 C 0.59690(7) 0.9448(2) 0.07626(6) 0.0174(2) Uani 1 1 d . .
H18 H 0.5578 0.9939 0.0819 0.021 Uiso 1 1 calc R U
F1 F 0.33837(4) 0.64924(17) 0.06574(4) 0.02346(19) Uani 1 1 d . .
F2 F 0.33525(5) 1.00711(17) 0.12280(5) 0.0249(2) Uani 1 1 d . .
F3 F 0.44504(5) 1.16840(17) 0.18948(4) 0.0266(2) Uani 1 1 d . .
F4 F 0.55595(5) 0.98434(16) 0.19606(5) 0.0270(2) 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'
P P 0.1023 0.0942 '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
C13 P1 C7 101.64(6)
C13 P1 C1 101.88(6)
C7 P1 C1 104.27(6)
C6 C1 C2 116.32(12)
C6 C1 P1 123.93(10)
C2 C1 P1 119.75(10)
C3 C2 C1 120.75(12)
C3 C2 I1 115.72(10)
C1 C2 I1 123.46(10)
F1 C3 C4 117.41(13)
F1 C3 C2 121.46(13)
C4 C3 C2 121.13(13)
F2 C4 C5 120.15(14)
F2 C4 C3 120.47(14)
C5 C4 C3 119.34(13)
F3 C5 C4 120.40(13)
F3 C5 C6 119.97(14)
C4 C5 C6 119.56(13)
F4 C6 C5 115.81(12)
F4 C6 C1 121.23(12)
C5 C6 C1 122.89(13)
C12 C7 C8 118.96(12)
C12 C7 P1 116.68(10)
C8 C7 P1 124.15(10)
C9 C8 C7 120.55(13)
C10 C9 C8 120.11(13)
C11 C10 C9 119.80(13)
C10 C11 C12 120.13(13)
C7 C12 C11 120.43(13)
C18 C13 C14 118.62(13)
C18 C13 P1 125.46(11)
C14 C13 P1 115.90(10)
C15 C14 C13 120.79(14)
C14 C15 C16 120.32(14)
C17 C16 C15 119.48(14)
C16 C17 C18 120.30(15)
C17 C18 C13 120.48(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C13 1.8339(15)
P1 C7 1.8356(13)
P1 C1 1.8471(14)
I1 C2 2.0920(13)
C1 C6 1.3945(19)
C1 C2 1.4123(18)
C2 C3 1.3875(19)
C3 F1 1.3469(16)
C3 C4 1.382(2)
C4 F2 1.3381(16)
C4 C5 1.379(2)
C5 F3 1.3349(17)
C5 C6 1.387(2)
C6 F4 1.3403(17)
C7 C12 1.3960(19)
C7 C8 1.3999(19)
C8 C9 1.3931(19)
C9 C10 1.391(2)
C10 C11 1.391(2)
C11 C12 1.397(2)
C13 C18 1.399(2)
C13 C14 1.4026(19)
C14 C15 1.385(2)
C15 C16 1.394(2)
C16 C17 1.391(2)
C17 C18 1.396(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
C13 P1 C1 C6 -73.55(13)
C7 P1 C1 C6 31.89(14)
C13 P1 C1 C2 106.47(11)
C7 P1 C1 C2 -148.09(11)
C6 C1 C2 C3 0.3(2)
P1 C1 C2 C3 -179.76(10)
C6 C1 C2 I1 177.15(10)
P1 C1 C2 I1 -2.88(16)
C1 C2 C3 F1 179.62(13)
I1 C2 C3 F1 2.50(17)
C1 C2 C3 C4 0.2(2)
I1 C2 C3 C4 -176.96(11)
F1 C3 C4 F2 -2.4(2)
C2 C3 C4 F2 177.07(13)
F1 C3 C4 C5 179.75(13)
C2 C3 C4 C5 -0.8(2)
F2 C4 C5 F3 -0.1(2)
C3 C4 C5 F3 177.72(14)
F2 C4 C5 C6 -176.90(14)
C3 C4 C5 C6 0.9(2)
F3 C5 C6 F4 -0.3(2)
C4 C5 C6 F4 176.52(14)
F3 C5 C6 C1 -177.32(14)
C4 C5 C6 C1 -0.5(2)
C2 C1 C6 F4 -176.97(13)
P1 C1 C6 F4 3.1(2)
C2 C1 C6 C5 -0.1(2)
P1 C1 C6 C5 179.95(12)
C13 P1 C7 C12 -162.92(11)
C1 P1 C7 C12 91.46(12)
C13 P1 C7 C8 11.72(13)
C1 P1 C7 C8 -93.90(13)
C12 C7 C8 C9 0.3(2)
P1 C7 C8 C9 -174.24(11)
C7 C8 C9 C10 -0.1(2)
C8 C9 C10 C11 -0.6(2)
C9 C10 C11 C12 1.2(2)
C8 C7 C12 C11 0.3(2)
P1 C7 C12 C11 175.23(12)
C10 C11 C12 C7 -1.1(2)
C7 P1 C13 C18 -104.38(13)
C1 P1 C13 C18 3.11(13)
C7 P1 C13 C14 77.12(11)
C1 P1 C13 C14 -175.39(10)
C18 C13 C14 C15 0.8(2)
P1 C13 C14 C15 179.39(11)
C13 C14 C15 C16 -1.2(2)
C14 C15 C16 C17 0.7(2)
C15 C16 C17 C18 0.2(2)
C16 C17 C18 C13 -0.6(2)
C14 C13 C18 C17 0.1(2)
P1 C13 C18 C17 -178.36(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189486
