#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/97/2019785.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_2019785
loop_
_publ_author_name
'Raffo, Pablo A.'
'Cukiernik, Fabio D.'
'Baggio, Ricardo F.'
_publ_section_title
;
 The three-component cocrystal
 1,3,5-trifluoro-2,4,6-triiodobenzene--pyridineN-oxide--water (1/2/1)
 built up by halogen bonds, hydrogen bonds and π--π interactions
;
_journal_coeditor_code           SK3575
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S205322961402796X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C6 F3 I3, 2C5 H5 N O, H2 O'
_chemical_formula_moiety         'C6 F3 I3, 2(C5 H5 N O), H2 O'
_chemical_formula_sum            'C16 H12 F3 I3 N2 O3'
_chemical_formula_weight         717.98
_chemical_name_systematic
;
1,3,5-Triiodo-2,4,6-trifluorobenzene--pyridine N-oxide--water (1/2/1)
;
_space_group_IT_number           15
_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   mixed
_audit_creation_method           SHELXL2014
_cell_angle_alpha                90.0
_cell_angle_beta                 94.727(7)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   14.2226(12)
_cell_length_b                   19.0094(18)
_cell_length_c                   7.5203(5)
_cell_measurement_reflns_used    2090
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.6000
_cell_measurement_theta_min      4.2960
_cell_volume                     2026.3(3)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1158
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur CCD (Eos, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6727
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.883
_diffrn_reflns_theta_min         3.586
_exptl_absorpt_coefficient_mu    4.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.744
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0354
_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)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1830
_reflns_number_total             2358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3575sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2019785
_cod_database_fobs_code          2019785
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
I I1 0.5000 0.70155(3) 0.2500 0.0697(2) Uani d 1
I I2 0.70350(2) 0.42760(2) 0.15588(4) 0.04207(14) Uani d 1
F F1 0.5000 0.3763(2) 0.2500 0.0550(11) Uani d 1
F F2 0.6537(2) 0.59032(16) 0.1621(4) 0.0510(7) Uani d 1
O O1 0.8668(3) 0.6459(2) 0.5808(5) 0.0560(10) Uani d 1
N N1 0.8666(3) 0.6535(2) 0.4053(5) 0.0413(9) Uani d 1
C C1 0.5000 0.4472(3) 0.2500 0.0319(13) Uani d 1
C C2 0.5813(3) 0.4823(3) 0.2083(6) 0.0352(10) Uani d 1
C C3 0.5777(3) 0.5545(3) 0.2059(6) 0.0376(11) Uani d 1
C C4 0.5000 0.5925(4) 0.2500 0.0372(14) Uani d 1
C C5 0.8508(4) 0.7170(3) 0.3336(8) 0.0574(14) Uani d 1
H H5 0.8392 0.7548 0.4069 0.069 Uiso calc 1
C C6 0.8514(5) 0.7272(3) 0.1536(8) 0.0667(17) Uani d 1
H H6 0.8415 0.7719 0.1053 0.080 Uiso calc 1
C C7 0.8670(4) 0.6707(4) 0.0442(7) 0.0594(15) Uani d 1
H H7 0.8675 0.6767 -0.0785 0.071 Uiso calc 1
C C8 0.8815(4) 0.6060(4) 0.1197(8) 0.0597(15) Uani d 1
H H8 0.8916 0.5671 0.0489 0.072 Uiso calc 1
C C9 0.8813(4) 0.5989(3) 0.3003(8) 0.0540(13) Uani d 1
H H9 0.8916 0.5547 0.3514 0.065 Uiso calc 1
O O1W 1.0000 0.5512(3) 0.7500 0.0665(16) Uani d 1
H H1W 0.9542(18) 0.5777(11) 0.713(9) 0.080 Uiso d 1
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 N1 C9 . . 121.1(4)
O1 N1 C5 . . 119.2(4)
C9 N1 C5 . . 119.7(5)
F1 C1 C2 . 2_655 118.6(3)
F1 C1 C2 . . 118.6(3)
C2 C1 C2 2_655 . 122.7(6)
C3 C2 C1 . . 116.8(4)
C3 C2 I2 . . 121.7(4)
C1 C2 I2 . . 121.5(4)
F2 C3 C2 . . 118.7(4)
F2 C3 C4 . . 118.0(5)
C2 C3 C4 . . 123.3(5)
C3 C4 C3 . 2_655 117.0(6)
C3 C4 I1 . . 121.5(3)
C3 C4 I1 2_655 . 121.5(3)
N1 C5 C6 . . 121.0(6)
N1 C5 H5 . . 119.5
C6 C5 H5 . . 119.5
C5 C6 C7 . . 119.5(6)
C5 C6 H6 . . 120.3
C7 C6 H6 . . 120.3
C8 C7 C6 . . 118.6(5)
C8 C7 H7 . . 120.7
C6 C7 H7 . . 120.7
C7 C8 C9 . . 119.4(6)
C7 C8 H8 . . 120.3
C9 C8 H8 . . 120.3
N1 C9 C8 . . 121.7(5)
N1 C9 H9 . . 119.1
C8 C9 H9 . . 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C4 . 2.072(7)
I2 C2 . 2.091(4)
F1 C1 . 1.349(7)
F2 C3 . 1.341(5)
O1 N1 . 1.328(5)
N1 C9 . 1.331(7)
N1 C5 . 1.332(7)
C1 C2 2_655 1.393(5)
C1 C2 . 1.393(5)
C2 C3 . 1.374(7)
C3 C4 . 1.383(6)
C4 C3 2_655 1.383(6)
C5 C6 . 1.368(8)
C5 H5 . 0.9300
C6 C7 . 1.382(9)
C6 H6 . 0.9300
C7 C8 . 1.364(9)
C7 H7 . 0.9300
C8 C9 . 1.365(8)
C8 H8 . 0.9300
C9 H9 . 0.9300
O1W H1W . 0.851(10)
