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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/72/7227269.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_7227269
loop_
_publ_author_name
'Som, Bozumeh'
'Salpage, Sahan R.'
'Son, Juno'
'Gu, Bing'
'Karakalos, Stavros G.'
'Smith, Mark D.'
'Shimizu, Linda S.'
_publ_section_title
;
 Pillars of assembled pyridyl bis-urea macrocycles: a robust synthon to
 organize diiodotetrafluorobenzenes
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              484
_journal_paper_doi               10.1039/C6CE02392D
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         '2(C6 F4 I2), C16 H18 N6 O2'
_chemical_formula_sum            'C28 H18 F8 I4 N6 O2'
_chemical_formula_weight         1130.08
_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   mixed
_audit_creation_date             2015-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-10-28 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                104.509(2)
_cell_angle_beta                 96.086(2)
_cell_angle_gamma                97.186(2)
_cell_formula_units_Z            1
_cell_length_a                   4.6564(3)
_cell_length_b                   12.7812(9)
_cell_length_c                   14.2764(9)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.51
_cell_volume                     807.71(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3550
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        27.220
_diffrn_reflns_theta_max         27.222
_diffrn_reflns_theta_min         2.514
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    3.943
_exptl_absorpt_correction_T_max  0.2612
_exptl_absorpt_correction_T_min  0.2072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0946 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.7933.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.323
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0247
_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)+(0.0145P)²+1.4492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3025
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02392d2.cif
_cod_data_source_block           bs185a
_cod_depositor_comments
'Adding full bibliography for 7227268--7227270.cif.'
_cod_original_cell_volume        807.70(9)
_cod_database_code               7227269
_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.
;
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.477
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7549(9) 0.2451(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 N2-H2 \\sim N1-H1
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I 0.67930(5) 0.40325(2) 0.56658(2) 0.01908(7) Uani 1 1 d .
I2 I 0.64668(5) 0.33708(2) 0.29552(2) 0.01745(7) Uani 1 1 d .
F1 F 0.9698(6) 0.13504(17) 0.23976(15) 0.0284(5) Uani 1 1 d .
F2 F 1.2636(6) 0.02405(19) 0.34346(17) 0.0357(6) Uani 1 1 d .
F3 F 1.2891(5) 0.07356(18) 0.54096(17) 0.0307(5) Uani 1 1 d .
F4 F 1.0122(5) 0.23120(18) 0.63358(14) 0.0246(5) Uani 1 1 d .
C11 C 0.8537(8) 0.2731(3) 0.4854(2) 0.0151(7) Uani 1 1 d .
C12 C 0.8424(8) 0.2486(3) 0.3835(3) 0.0166(7) Uani 1 1 d .
C13 C 0.9777(9) 0.1632(3) 0.3376(3) 0.0202(8) Uani 1 1 d .
C14 C 1.1278(9) 0.1049(3) 0.3897(3) 0.0230(8) Uani 1 1 d .
C15 C 1.1411(8) 0.1294(3) 0.4890(3) 0.0209(8) Uani 1 1 d .
C16 C 0.9988(8) 0.2114(3) 0.5357(2) 0.0183(8) Uani 1 1 d .
O1 O 0.4749(6) 0.45674(19) 0.16133(17) 0.0175(5) Uani 1 1 d .
N1 N 0.0062(7) 0.4140(3) 0.0831(2) 0.0172(7) Uani 1 1 d D
H1 H -0.146(8) 0.436(3) 0.088(3) 0.023(8) Uiso 1 1 d D
N2 N 0.2164(7) 0.5935(2) 0.1474(2) 0.0168(6) Uani 1 1 d D
H2 H 0.065(8) 0.606(3) 0.124(3) 0.023(8) Uiso 1 1 d D
N3 N 0.7200(7) 0.6994(2) 0.0666(2) 0.0159(6) Uani 1 1 d .
C1 C 0.2464(8) 0.4870(3) 0.1329(2) 0.0152(7) Uani 1 1 d .
C2 C 0.4502(9) 0.6813(3) 0.1996(2) 0.0199(8) Uani 1 1 d .
H2A H 0.6118 0.6496 0.2273 0.024 Uiso 1 1 calc R
H2B H 0.3769 0.7294 0.2547 0.024 Uiso 1 1 calc R
C3 C 0.5673(8) 0.7493(3) 0.1352(2) 0.0167(7) Uani 1 1 d .
C4 C 0.5169(9) 0.8557(3) 0.1466(3) 0.0217(8) Uani 1 1 d .
H4 H 0.4121 0.8888 0.1967 0.026 Uiso 1 1 calc R
C5 C 0.6223(9) 0.9135(3) 0.0836(3) 0.0240(9) Uani 1 1 d .
H5 H 0.5922 0.9870 0.0900 0.029 Uiso 1 1 calc R
C6 C 0.7710(9) 0.8621(3) 0.0116(3) 0.0205(8) Uani 1 1 d .
H6 H 0.8409 0.8991 -0.0335 0.025 Uiso 1 1 calc R
C7 C 0.8183(8) 0.7548(3) 0.0053(2) 0.0154(7) Uani 1 1 d .
C8 C 0.9927(8) 0.7015(3) -0.0715(2) 0.0182(8) Uani 1 1 d .
H8A H 0.9132 0.7120 -0.1350 0.022 Uiso 1 1 calc R
H8B H 1.1973 0.7397 -0.0547 0.022 Uiso 1 1 calc R
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
C12 C11 I1 123.3(3) . .
C16 C11 I1 117.8(3) . .
C16 C11 C12 118.8(3) . .
C11 C12 I2 124.3(3) . .
C13 C12 I2 117.3(2) . .
C13 C12 C11 118.4(3) . .
F1 C13 C12 121.0(3) . .
F1 C13 C14 117.5(3) . .
C14 C13 C12 121.6(3) . .
F2 C14 C13 120.4(3) . .
F2 C14 C15 119.7(3) . .
C15 C14 C13 120.0(4) . .
F3 C15 C14 120.5(3) . .
F3 C15 C16 120.2(3) . .
C14 C15 C16 119.3(3) . .
F4 C16 C11 120.9(3) . .
F4 C16 C15 117.2(3) . .
C15 C16 C11 121.9(3) . .
C1 N1 H1 115(3) . .
C1 N1 C8 119.2(3) . 2_665
C8 N1 H1 118(3) 2_665 .
C1 N2 H2 117(3) . .
C1 N2 C2 122.0(3) . .
C2 N2 H2 121(3) . .
C7 N3 C3 118.2(3) . .
O1 C1 N1 121.8(3) . .
O1 C1 N2 123.1(3) . .
N2 C1 N1 115.1(3) . .
N2 C2 H2A 109.0 . .
N2 C2 H2B 109.0 . .
N2 C2 C3 112.7(3) . .
H2A C2 H2B 107.8 . .
C3 C2 H2A 109.0 . .
C3 C2 H2B 109.0 . .
N3 C3 C2 116.0(3) . .
N3 C3 C4 122.8(3) . .
C4 C3 C2 121.2(3) . .
C3 C4 H4 120.6 . .
C3 C4 C5 118.8(3) . .
C5 C4 H4 120.6 . .
C4 C5 H5 120.7 . .
C6 C5 C4 118.6(3) . .
C6 C5 H5 120.7 . .
C5 C6 H6 120.3 . .
C5 C6 C7 119.4(3) . .
C7 C6 H6 120.3 . .
N3 C7 C6 122.1(3) . .
N3 C7 C8 119.3(3) . .
C6 C7 C8 118.6(3) . .
N1 C8 C7 115.0(3) 2_665 .
N1 C8 H8A 108.5 2_665 .
N1 C8 H8B 108.5 2_665 .
C7 C8 H8A 108.5 . .
C7 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C11 2.084(3) .
I2 C12 2.101(3) .
F1 C13 1.347(4) .
F2 C14 1.347(4) .
F3 C15 1.347(4) .
F4 C16 1.350(4) .
C11 C12 1.402(5) .
C11 C16 1.381(5) .
C12 C13 1.385(5) .
C13 C14 1.378(5) .
C14 C15 1.366(5) .
C15 C16 1.378(5) .
O1 C1 1.239(4) .
N1 H1 0.80(3) .
N1 C1 1.366(5) .
N1 C8 1.444(5) 2_665
N2 H2 0.80(3) .
N2 C1 1.352(5) .
N2 C2 1.450(5) .
N3 C3 1.349(5) .
N3 C7 1.337(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.512(5) .
C3 C4 1.382(5) .
C4 H4 0.9500 .
C4 C5 1.390(5) .
C5 H5 0.9500 .
C5 C6 1.377(5) .
C6 H6 0.9500 .
C6 C7 1.397(5) .
C7 C8 1.510(5) .
C8 N1 1.444(5) 2_665
C8 H8A 0.9900 .
C8 H8B 0.9900 .
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
N1 H1 O1 0.80(3) 2.16(4) 2.878(4) 151(4) 1_455
N2 H2 N3 0.80(3) 2.32(3) 3.083(4) 161(4) 1_455
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_4
I1 C11 C12 I2 -0.5(4) . .
I1 C11 C12 C13 177.0(3) . .
I1 C11 C16 F4 3.7(5) . .
I1 C11 C16 C15 -174.8(3) . .
I2 C12 C13 F1 -3.4(5) . .
I2 C12 C13 C14 175.9(3) . .
F1 C13 C14 F2 0.9(5) . .
F1 C13 C14 C15 -179.5(3) . .
F2 C14 C15 F3 0.1(6) . .
F2 C14 C15 C16 -179.3(3) . .
F3 C15 C16 F4 -0.9(5) . .
F3 C15 C16 C11 177.6(3) . .
C11 C12 C13 F1 178.9(3) . .
C11 C12 C13 C14 -1.8(6) . .
C12 C11 C16 F4 -179.2(3) . .
C12 C11 C16 C15 2.3(5) . .
C12 C13 C14 F2 -178.3(3) . .
C12 C13 C14 C15 1.3(6) . .
C13 C14 C15 F3 -179.5(3) . .
C13 C14 C15 C16 1.1(6) . .
C14 C15 C16 F4 178.5(3) . .
C14 C15 C16 C11 -2.9(6) . .
C16 C11 C12 I2 -177.5(3) . .
C16 C11 C12 C13 0.1(5) . .
N2 C2 C3 N3 -69.7(4) . .
N2 C2 C3 C4 109.9(4) . .
N3 C3 C4 C5 1.4(6) . .
N3 C7 C8 N1 10.6(5) . 2_665
C1 N2 C2 C3 114.5(4) . .
C2 N2 C1 O1 -1.3(5) . .
C2 N2 C1 N1 179.6(3) . .
C2 C3 C4 C5 -178.1(3) . .
C3 N3 C7 C6 1.0(5) . .
C3 N3 C7 C8 179.3(3) . .
C3 C4 C5 C6 0.5(6) . .
C4 C5 C6 C7 -1.6(6) . .
C5 C6 C7 N3 0.9(6) . .
C5 C6 C7 C8 -177.5(3) . .
C6 C7 C8 N1 -170.9(3) . 2_665
C7 N3 C3 C2 177.5(3) . .
C7 N3 C3 C4 -2.1(5) . .
C8 N1 C1 O1 6.3(5) 2_665 .
C8 N1 C1 N2 -174.6(3) 2_665 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7549(9)
2 0.2451(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203079
