#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:34:43 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249324.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_7249324
loop_
_publ_author_name
'Wang, Weizhou'
'Ji, Baoming'
_publ_section_title
;
 The C--I⋯O halogen bonding in crown ether chemistry
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5309
_journal_page_last               5313
_journal_paper_doi               10.1039/D4CE00853G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C10 H8 F4 I2 O2'
_chemical_formula_weight         489.96
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                94.007(7)
_cell_angle_beta                 103.778(7)
_cell_angle_gamma                113.576(7)
_cell_formula_units_Z            2
_cell_length_a                   7.5395(6)
_cell_length_b                   8.6077(7)
_cell_length_c                   12.2413(10)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2470
_cell_measurement_theta_min      3.7200
_cell_volume                     694.90(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2542
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5112
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    4.562
_exptl_absorpt_correction_T_max  0.6338
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0593(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2117
_reflns_number_total             2833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ce00853g2.cif
_cod_data_source_block           C4-I14
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7249319--7249331.cif.
;
_cod_original_cell_volume        694.90(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7249324
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5835(8) 0.5848(8) 0.9219(4) 0.0460(14) Uani 1 1 d . . .
C2 C 0.4656(8) 0.4102(8) 0.8912(4) 0.0464(14) Uani 1 1 d . . .
C3 C 0.3812(9) 0.3270(8) 0.9706(5) 0.0513(15) Uani 1 1 d . . .
C4 C 0.0665(8) 0.5843(8) 0.9133(4) 0.0475(14) Uani 1 1 d . . .
C5 C -0.0286(8) 0.4080(8) 0.8977(4) 0.0491(15) Uani 1 1 d . . .
C6 C -0.0946(9) 0.3259(8) 0.9819(5) 0.0532(15) Uani 1 1 d . . .
C7 C 0.8602(8) 0.1705(9) 0.5057(5) 0.0642(19) Uani 1 1 d . . .
H7A H 0.9520 0.2823 0.5532 0.077 Uiso 1 1 calc R . .
H7B H 0.9370 0.1307 0.4672 0.077 Uiso 1 1 calc R . .
C8 C 0.6470(9) 0.3149(8) 0.4619(5) 0.0627(18) Uani 1 1 d . . .
H8A H 0.7092 0.4196 0.4332 0.075 Uiso 1 1 calc R . .
H8B H 0.6943 0.3423 0.5449 0.075 Uiso 1 1 calc R . .
C9 C 0.4222(10) 0.2502(9) 0.4228(5) 0.0626(18) Uani 1 1 d . . .
H9A H 0.3872 0.3457 0.4339 0.075 Uiso 1 1 calc R . .
H9B H 0.3725 0.2014 0.3417 0.075 Uiso 1 1 calc R . .
C10 C 0.2222(9) -0.0470(8) 0.4199(5) 0.0564(16) Uani 1 1 d . . .
H10A H 0.3129 -0.0776 0.3884 0.068 Uiso 1 1 calc R . .
H10B H 0.1124 -0.0530 0.3568 0.068 Uiso 1 1 calc R . .
F1 F 0.6706(5) 0.6730(5) 0.8481(3) 0.0659(10) Uani 1 1 d . . .
F2 F 0.2627(6) 0.1576(5) 0.9458(3) 0.0801(12) Uani 1 1 d . . .
F3 F -0.0560(6) 0.3133(5) 0.7980(3) 0.0756(12) Uani 1 1 d . . .
F4 F -0.1875(7) 0.1518(5) 0.9592(4) 0.0896(14) Uani 1 1 d . . .
I1 I 0.41135(6) 0.27600(6) 0.72918(3) 0.0594(2) Uani 1 1 d . . .
I2 I 0.16497(7) 0.70805(7) 0.78425(4) 0.0684(2) Uani 1 1 d . . .
O1 O 0.7053(6) 0.1887(6) 0.4221(3) 0.0573(11) Uani 1 1 d . . .
O2 O 0.3275(6) 0.1220(5) 0.4844(3) 0.0529(11) 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'
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
_geom_angle_publ_flag
F1 C1 C2 120.3(5) . . ?
F1 C1 C3 118.6(5) . 2_667 ?
C2 C1 C3 121.1(5) . 2_667 ?
C3 C2 C1 117.6(5) . . ?
C3 C2 I1 121.0(5) . . ?
C1 C2 I1 121.4(4) . . ?
F2 C3 C2 120.7(5) . . ?
F2 C3 C1 118.0(5) . 2_667 ?
C2 C3 C1 121.3(6) . 2_667 ?
C6 C4 C5 116.7(5) 2_567 . ?
C6 C4 I2 122.1(5) 2_567 . ?
C5 C4 I2 121.2(4) . . ?
F3 C5 C4 119.4(5) . . ?
F3 C5 C6 119.1(6) . . ?
C4 C5 C6 121.5(5) . . ?
F4 C6 C4 120.6(5) . 2_567 ?
F4 C6 C5 117.7(5) . . ?
C4 C6 C5 121.8(6) 2_567 . ?
O1 C7 C10 112.5(5) . 2_656 ?
O1 C7 H7A 109.1 . . ?
C10 C7 H7A 109.1 2_656 . ?
O1 C7 H7B 109.1 . . ?
C10 C7 H7B 109.1 2_656 . ?
H7A C7 H7B 107.8 . . ?
O1 C8 C9 110.6(5) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O2 C9 C8 111.2(5) . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O2 C10 C7 109.8(5) . 2_656 ?
O2 C10 H10A 109.7 . . ?
C7 C10 H10A 109.7 2_656 . ?
O2 C10 H10B 109.7 . . ?
C7 C10 H10B 109.7 2_656 . ?
H10A C10 H10B 108.2 . . ?
C8 O1 C7 113.9(5) . . ?
C10 O2 C9 114.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.344(6) . ?
C1 C2 1.372(8) . ?
C1 C3 1.383(8) 2_667 ?
C2 C3 1.374(7) . ?
C2 I1 2.086(5) . ?
C3 F2 1.335(7) . ?
C3 C1 1.383(8) 2_667 ?
C4 C6 1.374(8) 2_567 ?
C4 C5 1.369(9) . ?
C4 I2 2.084(5) . ?
C5 F3 1.343(6) . ?
C5 C6 1.370(8) . ?
C6 F4 1.350(7) . ?
C6 C4 1.374(8) 2_567 ?
C7 O1 1.427(7) . ?
C7 C10 1.491(8) 2_656 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.421(7) . ?
C8 C9 1.494(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.428(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.410(7) . ?
C10 C7 1.491(8) 2_656 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 179.8(5) . . . . ?
C3 C1 C2 C3 1.1(10) 2_667 . . . ?
F1 C1 C2 I1 -1.4(8) . . . . ?
C3 C1 C2 I1 179.9(4) 2_667 . . . ?
C1 C2 C3 F2 179.1(6) . . . . ?
I1 C2 C3 F2 0.2(8) . . . . ?
C1 C2 C3 C1 -1.1(10) . . . 2_667 ?
I1 C2 C3 C1 -179.9(4) . . . 2_667 ?
C6 C4 C5 F3 -178.5(5) 2_567 . . . ?
I2 C4 C5 F3 1.0(8) . . . . ?
C6 C4 C5 C6 0.8(10) 2_567 . . . ?
I2 C4 C5 C6 -179.7(4) . . . . ?
F3 C5 C6 F4 -1.0(9) . . . . ?
C4 C5 C6 F4 179.7(6) . . . . ?
F3 C5 C6 C4 178.5(5) . . . 2_567 ?
C4 C5 C6 C4 -0.8(11) . . . 2_567 ?
O1 C8 C9 O2 73.1(7) . . . . ?
C9 C8 O1 C7 -137.4(5) . . . . ?
C10 C7 O1 C8 86.5(7) 2_656 . . . ?
C7 C10 O2 C9 176.8(5) 2_656 . . . ?
C8 C9 O2 C10 -108.5(6) . . . . ?
