#------------------------------------------------------------------------------
#$Date: 2023-02-08 12:22:45 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106727.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_8106727
loop_
_publ_author_name
'Dang, Limin'
'Yang, Jiangnan'
'Liu, Hui'
'Wang, Weizhou'
_publ_section_title
;
 Halogen bonds and π--π interactions in the crystal structure of
 1,3,5-trifluoro-2,4,6-triiodobenzene--N,N-dimethylformamide (1/1),
 C9H7F3I3NO
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              937
_journal_page_last               938
_journal_paper_doi               10.1515/ncrs-2017-0089
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C6 F3 I3, C3 H7 N O'
_chemical_formula_sum            'C9 H7 F3 I3 N O'
_chemical_formula_weight         582.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 92.208(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5581(4)
_cell_length_b                   20.9303(11)
_cell_length_c                   9.3548(5)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.1950
_cell_measurement_theta_min      3.9140
_cell_volume                     1478.77(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -85.00 -35.00   1.00    3.59    --  -12.53-178.00 -60.00   50
  2  ω    -56.00  83.00   1.00    3.59    --   13.55   0.00 -30.00  139
  3  ω    -49.00  31.00   1.00    3.59    --   13.55 -38.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0272377000
_diffrn_orient_matrix_UB_12      -0.0217817000
_diffrn_orient_matrix_UB_13      0.0545971000
_diffrn_orient_matrix_UB_21      0.0516771000
_diffrn_orient_matrix_UB_22      -0.0167476000
_diffrn_orient_matrix_UB_23      -0.0494105000
_diffrn_orient_matrix_UB_31      0.0735837000
_diffrn_orient_matrix_UB_32      0.0198258000
_diffrn_orient_matrix_UB_33      0.0182544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.618
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.00670(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0161P)²+1.6425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0610
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2324
_reflns_number_total             2695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0089_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1478.78(13)
_cod_database_code               8106727
_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.
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2017-03-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.814
loop_
_space_group_symop_operation_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_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.75542(6) 0.54578(2) 0.91796(4) 0.07562(18) Uani 1 1 d . . . . .
I2 I 0.62380(5) 0.35271(2) 0.44873(4) 0.05582(15) Uani 1 1 d . . . . .
I3 I 0.86979(5) 0.62061(2) 0.30805(4) 0.05378(15) Uani 1 1 d . . . . .
F1 F 0.6449(4) 0.41963(16) 0.7510(3) 0.0635(9) Uani 1 1 d . . . . .
F2 F 0.7455(4) 0.47525(15) 0.2763(3) 0.0612(9) Uani 1 1 d . . . . .
F3 F 0.8575(5) 0.62321(15) 0.6439(4) 0.0643(9) Uani 1 1 d . . . . .
C1 C 0.7510(7) 0.5220(3) 0.7017(5) 0.0454(13) Uani 1 1 d . . . . .
C2 C 0.6981(7) 0.4625(3) 0.6550(5) 0.0438(13) Uani 1 1 d . . . . .
C3 C 0.6973(6) 0.4448(2) 0.5121(6) 0.0414(12) Uani 1 1 d . . . . .
C4 C 0.7471(6) 0.4911(3) 0.4161(5) 0.0446(13) Uani 1 1 d . . . . .
C5 C 0.7998(6) 0.5512(2) 0.4553(5) 0.0391(12) Uani 1 1 d . . . . .
C6 C 0.8026(6) 0.5650(2) 0.6003(6) 0.0431(13) Uani 1 1 d . . . . .
O1 O 0.9966(8) 0.2729(3) 0.8581(7) 0.112(2) Uani 1 1 d . . . . .
N1 N 0.7267(8) 0.2921(3) 0.9394(7) 0.0774(17) Uani 1 1 d . . . . .
C7 C 0.8320(14) 0.2689(4) 0.8478(9) 0.095(3) Uani 1 1 d . . . . .
H7 H 0.7820 0.2477 0.7686 0.113 Uiso 1 1 calc R . . . .
C8 C 0.7941(19) 0.3249(7) 1.0568(12) 0.195(6) Uani 1 1 d . . . . .
H8A H 0.7475 0.3676 1.0559 0.292 Uiso 1 1 calc GR . . . .
H8B H 0.9208 0.3265 1.0538 0.292 Uiso 1 1 calc GR . . . .
H8C H 0.7609 0.3035 1.1425 0.292 Uiso 1 1 calc GR . . . .
C9 C 0.5371(12) 0.2862(5) 0.9276(13) 0.157(5) Uani 1 1 d . . . . .
H9A H 0.4956 0.2647 1.0106 0.236 Uiso 1 1 calc GR . . . .
H9B H 0.5042 0.2621 0.8435 0.236 Uiso 1 1 calc GR . . . .
H9C H 0.4849 0.3280 0.9209 0.236 Uiso 1 1 calc GR . . . .
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'
I I -0.4742 1.8119 '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'
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
C2 C1 I1 121.3(4) . .
C2 C1 C6 117.4(5) . .
C6 C1 I1 121.3(4) . .
F1 C2 C1 118.9(5) . .
F1 C2 C3 118.5(5) . .
C1 C2 C3 122.6(5) . .
C2 C3 I2 120.7(4) . .
C4 C3 I2 122.6(4) . .
C4 C3 C2 116.6(5) . .
F2 C4 C3 117.7(5) . .
F2 C4 C5 118.6(5) . .
C5 C4 C3 123.7(5) . .
C4 C5 I3 123.0(4) . .
C4 C5 C6 116.6(5) . .
C6 C5 I3 120.4(4) . .
F3 C6 C1 118.4(5) . .
F3 C6 C5 118.5(5) . .
C1 C6 C5 123.0(5) . .
C7 N1 C8 120.0(9) . .
C7 N1 C9 123.8(9) . .
C8 N1 C9 116.2(9) . .
O1 C7 N1 124.3(9) . .
O1 C7 H7 117.9 . .
N1 C7 H7 117.9 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.082(5) .
I2 C3 2.086(5) .
I3 C5 2.085(5) .
F1 C2 1.342(6) .
F2 C4 1.349(5) .
F3 C6 1.346(6) .
C1 C2 1.374(7) .
C1 C6 1.375(7) .
C2 C3 1.387(7) .
C3 C4 1.382(7) .
C4 C5 1.365(7) .
C5 C6 1.387(7) .
O1 C7 1.247(9) .
N1 C7 1.287(9) .
N1 C8 1.376(12) .
N1 C9 1.438(10) .
C7 H7 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
