#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:03:39 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/25/7232580.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_7232580
loop_
_publ_author_name
'Nemec, Vinko'
'Fotović, Luka'
'Vitasović, Toni'
'Cinčić, Dominik'
_publ_section_title
;
 Halogen bonding of the aldehyde oxygen atom in cocrystals of aromatic
 aldehydes and 1,4-diiodotetrafluorobenzene
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3251
_journal_paper_doi               10.1039/C9CE00340A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H11 N O)'
_chemical_formula_sum            'C24 H22 F4 I2 N2 O2'
_chemical_formula_weight         700.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-08 deposited with the CCDC.    2019-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                100.288(5)
_cell_angle_beta                 105.696(5)
_cell_angle_gamma                110.297(6)
_cell_formula_units_Z            1
_cell_length_a                   8.1668(5)
_cell_length_b                   8.4423(6)
_cell_length_c                   10.8612(5)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    295
_cell_measurement_theta_max      36.3640
_cell_measurement_theta_min      3.7384
_cell_volume                     644.64(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6447
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         4.301
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.491
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0308
_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)+(0.0312P)²+0.0112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2327
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00340a2.cif
_cod_data_source_block           dmab_2_14tfib
_cod_depositor_comments
'Adding full bibliography for 7232576--7232580.cif.'
_cod_original_cell_volume        644.64(7)
_cod_database_code               7232580
_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.
;
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
I1 I 0.74231(3) 0.74708(3) 0.16010(2) 0.06628(12) Uani 1 1 d . .
F2 F 1.0510(4) 1.3406(3) 0.0336(3) 0.0971(8) Uani 1 1 d . .
F1 F 0.8570(4) 1.1510(4) 0.1585(3) 0.0990(9) Uani 1 1 d . .
O1 O 0.5564(5) 0.5116(4) 0.2914(3) 0.0920(9) Uani 1 1 d . .
N1 N 0.1964(4) -0.2255(4) 0.4092(3) 0.0644(8) Uani 1 1 d . .
C6 C 0.3723(5) 0.2258(5) 0.3884(4) 0.0597(9) Uani 1 1 d . .
H6 H 0.3796 0.3357 0.4300 0.072 Uiso 1 1 calc R U
C4 C 0.2756(4) -0.0851(5) 0.3682(3) 0.0521(8) Uani 1 1 d . .
C1 C 0.4433(5) 0.2100(5) 0.2861(4) 0.0579(9) Uani 1 1 d . .
C10 C 0.8958(5) 0.8996(5) 0.0653(3) 0.0530(8) Uani 1 1 d . .
C5 C 0.2923(5) 0.0843(5) 0.4291(4) 0.0572(8) Uani 1 1 d . .
H5 H 0.2478 0.0999 0.4986 0.069 Uiso 1 1 calc R U
C7 C 0.5324(6) 0.3600(6) 0.2439(4) 0.0720(11) Uani 1 1 d . .
H7 H 0.5752 0.3386 0.1742 0.086 Uiso 1 1 calc R U
C9 C 0.1113(6) -0.2144(6) 0.5099(4) 0.0766(11) Uani 1 1 d . .
H9A H 0.1852 -0.1030 0.5792 0.115 Uiso 1 1 calc R U
H9B H 0.1053 -0.3094 0.5482 0.115 Uiso 1 1 calc R U
H9C H -0.0128 -0.2234 0.4690 0.115 Uiso 1 1 calc R U
C11 C 0.9276(5) 1.0730(5) 0.0804(4) 0.0593(9) Uani 1 1 d . .
C3 C 0.3490(5) -0.0996(5) 0.2658(4) 0.0632(9) Uani 1 1 d . .
H3 H 0.3431 -0.2088 0.2243 0.076 Uiso 1 1 calc R U
C12 C 1.0281(5) 1.1716(5) 0.0162(4) 0.0611(9) Uani 1 1 d . .
C2 C 0.4281(5) 0.0425(6) 0.2265(4) 0.0639(10) Uani 1 1 d . .
H2 H 0.4738 0.0279 0.1575 0.077 Uiso 1 1 calc R U
C8 C 0.1695(7) -0.4016(6) 0.3414(6) 0.0944(15) Uani 1 1 d . .
H8A H 0.0674 -0.4477 0.2570 0.142 Uiso 1 1 calc R U
H8B H 0.1415 -0.4775 0.3960 0.142 Uiso 1 1 calc R U
H8C H 0.2815 -0.3963 0.3264 0.142 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 C8 121.1(3) . .
C4 N1 C9 122.6(3) . .
C8 N1 C9 115.8(3) . .
C5 C6 C1 121.6(4) . .
C5 C6 H6 119.2 . .
C1 C6 H6 119.2 . .
N1 C4 C3 122.1(3) . .
N1 C4 C5 121.2(3) . .
C3 C4 C5 116.7(3) . .
C6 C1 C2 117.1(3) . .
C6 C1 C7 122.2(4) . .
C2 C1 C7 120.7(4) . .
C11 C10 C12 116.6(3) . 2_775
C11 C10 I1 122.7(2) . .
C12 C10 I1 120.7(3) 2_775 .
C6 C5 C4 121.3(3) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
O1 C7 C1 125.8(4) . .
O1 C7 H7 117.1 . .
C1 C7 H7 117.1 . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
F1 C11 C10 119.7(3) . .
F1 C11 C12 118.3(3) . .
C10 C11 C12 122.0(3) . .
C2 C3 C4 121.2(4) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
F2 C12 C10 119.7(3) . 2_775
F2 C12 C11 118.8(3) . .
C10 C12 C11 121.4(3) 2_775 .
C3 C2 C1 122.0(3) . .
C3 C2 H2 119.0 . .
C1 C2 H2 119.0 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C10 2.084(3) .
F2 C12 1.344(4) .
F1 C11 1.348(4) .
O1 C7 1.216(5) .
N1 C4 1.355(4) .
N1 C8 1.447(5) .
N1 C9 1.452(5) .
C6 C5 1.361(5) .
C6 C1 1.393(5) .
C6 H6 0.9300 .
C4 C3 1.405(5) .
C4 C5 1.406(5) .
C1 C2 1.393(5) .
C1 C7 1.447(5) .
C10 C11 1.365(5) .
C10 C12 1.377(5) 2_775
C5 H5 0.9300 .
C7 H7 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C11 C12 1.377(5) .
C3 C2 1.354(5) .
C3 H3 0.9300 .
C12 C10 1.377(5) 2_775
C2 H2 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
