#------------------------------------------------------------------------------
#$Date: 2017-05-11 08:15:53 +0300 (Thu, 11 May 2017) $
#$Revision: 196623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/60/1546013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546013
loop_
_publ_author_name
'Cavallo, Gabriella'
'Murray, Jane S.'
'Politzer, Peter'
'Pilati, Tullio'
'Ursini, Maurizio'
'Resnati, Giuseppe'
_publ_section_title
;
 Halogen bonding in hypervalent iodine and bromine derivatives: halonium
 salts
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252517004262
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C12 H10 I 1+, F6 P 1-'
_chemical_formula_sum            'C12 H10 F6 I P'
_chemical_formula_weight         426.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.195(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9721(5)
_cell_length_b                   12.9442(12)
_cell_length_c                   18.387(2)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      49.89
_cell_measurement_theta_min      2.73
_cell_volume                     1413.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXTL
_computing_structure_refinement
'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            77147
_diffrn_reflns_theta_full        50.00
_diffrn_reflns_theta_max         50.26
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_T_max  0.4415
_exptl_absorpt_correction_T_min  0.3579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.481
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         14804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0242
_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)+(0.0279P)²+0.5366P], where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                12120
_reflns_number_total             14805
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lc5079.cif
_cod_data_source_block           gc140LT
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1546013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_adp
I1 I 0.79933(2) 0.35808(2) 0.08706(2) 0.01530(1) Uani 1 1 d .
C1 C 1.06619(13) 0.36596(6) 0.17255(4) 0.01541(10) Uani 1 1 d .
C2 C 1.06419(16) 0.30065(8) 0.23226(5) 0.02046(13) Uani 1 1 d .
H2 H 0.951(3) 0.2509(14) 0.2360(10) 0.025 Uiso 1 1 d U
C3 C 1.24265(18) 0.30726(9) 0.28747(5) 0.02374(16) Uani 1 1 d .
H3 H 1.245(3) 0.2688(14) 0.3275(10) 0.028 Uiso 1 1 d U
C4 C 1.41313(18) 0.37949(9) 0.28262(5) 0.02316(15) Uani 1 1 d .
H4 H 1.535(3) 0.3816(15) 0.3184(11) 0.028 Uiso 1 1 d U
C5 C 1.40795(16) 0.44544(8) 0.22290(5) 0.02056(13) Uani 1 1 d .
H5 H 1.524(3) 0.4968(14) 0.2220(9) 0.025 Uiso 1 1 d U
C6 C 1.23337(14) 0.43901(7) 0.16599(5) 0.01693(11) Uani 1 1 d .
H6 H 1.224(3) 0.4794(13) 0.1246(9) 0.020 Uiso 1 1 d U
C7 C 0.71712(14) 0.20246(6) 0.10017(5) 0.01668(11) Uani 1 1 d .
C8 C 0.5551(2) 0.17919(8) 0.14581(7) 0.02738(19) Uani 1 1 d .
H8 H 0.485(3) 0.2319(15) 0.1718(10) 0.033 Uiso 1 1 d U
C9 C 0.4934(2) 0.07545(9) 0.15192(9) 0.0329(2) Uani 1 1 d .
H9 H 0.383(4) 0.0601(17) 0.1808(12) 0.039 Uiso 1 1 d U
C10 C 0.5913(2) 0.00037(8) 0.11244(7) 0.0313(2) Uani 1 1 d .
H10 H 0.535(4) -0.0735(16) 0.1203(11) 0.038 Uiso 1 1 d U
C11 C 0.7509(3) 0.02636(9) 0.06680(9) 0.0385(3) Uani 1 1 d .
H11 H 0.811(4) -0.0272(18) 0.0379(13) 0.046 Uiso 1 1 d U
C12 C 0.8177(3) 0.12873(8) 0.06010(7) 0.0297(2) Uani 1 1 d .
H12 H 0.924(4) 0.1414(15) 0.0297(12) 0.036 Uiso 1 1 d U
P1 P 0.71377(4) 0.66972(2) 0.07020(2) 0.01586(3) Uani 1 1 d .
F1 F 0.90542(13) 0.58374(6) 0.07093(5) 0.03528(17) Uani 1 1 d .
F2 F 0.68860(12) 0.66992(7) -0.01761(3) 0.02809(13) Uani 1 1 d .
F3 F 0.52572(13) 0.58121(6) 0.06858(5) 0.03232(15) Uani 1 1 d .
F4 F 0.89906(16) 0.75815(7) 0.06994(5) 0.03556(17) Uani 1 1 d .
F5 F 0.51598(17) 0.75441(6) 0.06717(5) 0.03828(19) Uani 1 1 d .
F6 F 0.73559(19) 0.67010(10) 0.15711(4) 0.0457(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
C7 I1 C1 97.35(3)
C2 C1 C6 123.45(8)
C2 C1 I1 119.24(6)
C6 C1 I1 117.31(6)
C1 C2 C3 117.92(9)
C1 C2 H2 122.9(11)
C3 C2 H2 119.2(11)
C4 C3 C2 120.13(9)
C4 C3 H3 119.0(12)
C2 C3 H3 120.7(12)
C5 C4 C3 120.63(9)
C5 C4 H4 119.5(12)
C3 C4 H4 119.9(12)
C4 C5 C6 120.43(9)
C4 C5 H5 119.0(11)
C6 C5 H5 120.5(11)
C1 C6 C5 117.41(8)
C1 C6 H6 118.6(10)
C5 C6 H6 124.0(10)
C8 C7 C12 123.15(9)
C8 C7 I1 117.93(6)
C12 C7 I1 118.83(7)
C7 C8 C9 117.75(10)
C7 C8 H8 121.4(11)
C9 C8 H8 120.9(11)
C10 C9 C8 120.22(11)
C10 C9 H9 121.8(14)
C8 C9 H9 118.0(14)
C11 C10 C9 120.55(10)
C11 C10 H10 124.7(12)
C9 C10 H10 114.7(12)
C10 C11 C12 120.64(11)
C10 C11 H11 118.7(14)
C12 C11 H11 120.6(14)
C7 C12 C11 117.68(11)
C7 C12 H12 125.3(12)
C11 C12 H12 117.0(12)
F6 P1 F4 91.10(5)
F6 P1 F1 90.73(6)
F4 P1 F1 90.19(5)
F6 P1 F3 90.12(6)
F4 P1 F3 178.74(5)
F1 P1 F3 90.12(4)
F6 P1 F2 179.28(6)
F4 P1 F2 89.17(4)
F1 P1 F2 89.93(5)
F3 P1 F2 89.60(5)
F6 P1 F5 90.74(6)
F4 P1 F5 91.03(5)
F1 P1 F5 178.07(6)
F3 P1 F5 88.63(5)
F2 P1 F5 88.59(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C7 2.0935(8)
I1 C1 2.1167(9)
C1 C2 1.3867(11)
C1 C6 1.3897(11)
C2 C3 1.3929(14)
C2 H2 0.939(18)
C3 C4 1.3922(16)
C3 H3 0.887(19)
C4 C5 1.3885(14)
C4 H4 0.93(2)
C5 C6 1.3976(13)
C5 H5 0.960(18)
C6 H6 0.920(17)
C7 C8 1.3806(13)
C7 C12 1.3821(13)
C8 C9 1.4002(15)
C8 H8 0.954(19)
C9 C10 1.3800(19)
C9 H9 0.91(2)
C10 C11 1.378(2)
C10 H10 1.03(2)
C11 C12 1.3931(17)
C11 H11 0.97(2)
C12 H12 0.90(2)
P1 F6 1.5893(8)
P1 F4 1.5924(8)
P1 F1 1.5955(8)
P1 F3 1.6024(7)
P1 F2 1.6053(7)
P1 F5 1.6080(8)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F6 0.939(18) 2.585(18) 3.3143(14) 134.8(14) 2_645
C6 H6 F1 0.920(17) 2.453(17) 3.1084(12) 128.4(13) .
C6 H6 F3 0.920(17) 2.538(17) 3.2124(11) 130.5(13) 1_655
C12 H12 F4 0.90(2) 2.57(2) 3.4050(14) 154.7(18) 3_765
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
C6 C1 C2 C3 -1.69(14)
I1 C1 C2 C3 179.68(7)
C1 C2 C3 C4 1.54(15)
C2 C3 C4 C5 -0.15(17)
C3 C4 C5 C6 -1.20(16)
C2 C1 C6 C5 0.38(13)
I1 C1 C6 C5 179.04(6)
C4 C5 C6 C1 1.08(13)
C12 C7 C8 C9 0.80(19)
I1 C7 C8 C9 177.24(10)
C7 C8 C9 C10 -0.8(2)
C8 C9 C10 C11 0.2(2)
C9 C10 C11 C12 0.5(3)
C8 C7 C12 C11 -0.1(2)
I1 C7 C12 C11 -176.54(12)
C10 C11 C12 C7 -0.5(2)
