#------------------------------------------------------------------------------
#$Date: 2020-12-09 03:49:17 +0200 (Wed, 09 Dec 2020) $
#$Revision: 259666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/75/7127506.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_7127506
loop_
_publ_author_name
'Vainauskas, Jogirdas'
'Topić, Filip'
'Bushuyev, Oleksandr S.'
'Barrett, Christoper J.'
'Friščić, Tomislav'
_publ_section_title
;
 Halogen bonding to the azulene π-system: cocrystal design of
 pleochroism.
;
_journal_issue                   96
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15145
_journal_page_last               15148
_journal_paper_doi               10.1039/d0cc04758a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '3(C6 F4 I2), 2(C10 H8)'
_chemical_formula_sum            'C38 H16 F12 I6'
_chemical_formula_weight         1461.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                73.9375(13)
_cell_angle_beta                 80.8173(15)
_cell_angle_gamma                85.0271(16)
_cell_formula_units_Z            1
_cell_length_a                   5.9617(2)
_cell_length_b                   12.0425(4)
_cell_length_c                   14.9758(5)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    253.0(1)
_cell_measurement_theta_max      72.52
_cell_measurement_theta_min      3.10
_cell_volume                     1018.93(6)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253.0(1)
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14753
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         72.728
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_exptl_absorpt_coefficient_mu    36.666
_exptl_absorpt_correction_T_max  0.2335
_exptl_absorpt_correction_T_min  0.0032
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    2.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.942
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.098
_refine_diff_density_max         1.582
_refine_diff_density_min         -2.329
_refine_diff_density_rms         0.259
_refine_ls_extinction_coef       0.0071(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0719
_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)+(0.1571P)²+2.7429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3210
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04758a2.cif
_cod_data_source_block           azu_14tfib_2-3_253K
_cod_database_code               7127506
_shelx_shelxl_version_number     2018/3
_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_min   0.013
_shelx_estimated_absorpt_t_max   0.124
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.3335(15) 0.4958(7) 0.3180(5) 0.059(2) Uani 1 1 d D . . . .
H1A H 0.203803 0.483332 0.362550 0.071 Uiso 1 1 calc R U . . .
C2A C 0.5111(14) 0.5659(7) 0.3150(6) 0.067(3) Uani 1 1 d D . . . .
H2A H 0.515759 0.608467 0.357804 0.081 Uiso 1 1 calc R U . . .
C3A C 0.6809(16) 0.5638(7) 0.2392(6) 0.066(3) Uani 1 1 d D . . . .
H3A H 0.814009 0.604159 0.223403 0.080 Uiso 1 1 calc R U . . .
C4A C 0.6147(12) 0.4901(6) 0.1912(5) 0.060(2) Uani 1 1 d D . . . .
C5A C 0.7337(15) 0.4647(7) 0.1119(6) 0.066(2) Uani 1 1 d D . . . .
H5A H 0.870393 0.501220 0.088874 0.080 Uiso 1 1 calc R U . . .
C6A C 0.6794(14) 0.3939(7) 0.0624(6) 0.055(2) Uani 1 1 d D . . . .
H6A H 0.787507 0.387080 0.011847 0.066 Uiso 1 1 calc R U . . .
C7A C 0.4865(13) 0.3301(7) 0.0759(6) 0.057(2) Uani 1 1 d D . . . .
H7A H 0.481757 0.288083 0.032776 0.068 Uiso 1 1 calc R U . . .
C8A C 0.3005(16) 0.3218(7) 0.1462(6) 0.064(2) Uani 1 1 d D . . . .
H8A H 0.188363 0.274265 0.143356 0.077 Uiso 1 1 calc R U . . .
C9A C 0.2563(13) 0.3727(7) 0.2191(6) 0.058(2) Uani 1 1 d D . . . .
H9A H 0.120067 0.354217 0.258637 0.070 Uiso 1 1 calc R U . . .
C10A C 0.3869(12) 0.4474(6) 0.2414(5) 0.058(2) Uani 1 1 d D . . . .
C1S C 0.8699(15) 0.1949(7) 0.5474(5) 0.0481(18) Uani 1 1 d . . . . .
C2S C 0.8234(14) 0.0777(7) 0.5718(6) 0.0472(17) Uani 1 1 d . . . . .
C3S C 0.9348(14) -0.0038(7) 0.6314(6) 0.0461(17) Uani 1 1 d . . . . .
C4S C 1.1115(13) 0.0245(6) 0.6729(5) 0.0420(15) Uani 1 1 d . . . . .
C5S C 1.1553(15) 0.1391(7) 0.6499(6) 0.0477(17) Uani 1 1 d . . . . .
C6S C 1.0402(16) 0.2229(7) 0.5886(6) 0.0494(18) Uani 1 1 d . . . . .
F1S F 0.6576(11) 0.0447(6) 0.5342(5) 0.0736(16) Uani 1 1 d . . . . .
F2S F 0.8861(10) -0.1159(4) 0.6509(5) 0.0669(14) Uani 1 1 d . . . . .
F3S F 1.3216(12) 0.1726(5) 0.6874(5) 0.0727(16) Uani 1 1 d . . . . .
F4S F 1.0946(12) 0.3337(5) 0.5693(5) 0.0743(17) Uani 1 1 d . . . . .
I1S I 0.69716(13) 0.31806(6) 0.45441(4) 0.0697(3) Uani 1 1 d . . . . .
I2S I 1.28727(11) -0.10127(5) 0.76275(4) 0.0616(3) Uani 1 1 d . . . . .
C1T C 0.1158(14) 0.9135(6) 0.0627(5) 0.0398(15) Uani 1 1 d . . . . .
C2T C -0.0554(15) 0.8873(6) 0.0203(6) 0.0440(17) Uani 1 1 d . . . . .
C3T C -0.1641(15) 0.9716(7) -0.0407(6) 0.0446(17) Uani 1 1 d . . . . .
F1T F -0.3318(12) 0.9405(5) -0.0796(5) 0.0719(18) Uani 1 1 d . . . . .
F2T F -0.1113(11) 0.7766(4) 0.0384(5) 0.0647(15) Uani 1 1 d . . . . .
I1T I 0.28519(10) 0.78627(4) 0.15547(3) 0.0536(3) 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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
C2A C1A C10A 107.4(6) . . ?
C2A C1A H1A 126.3 . . ?
C10A C1A H1A 126.3 . . ?
C1A C2A C3A 111.3(7) . . ?
C1A C2A H2A 124.4 . . ?
C3A C2A H2A 124.4 . . ?
C2A C3A C4A 107.8(6) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 126.4(6) . . ?
C5A C4A C10A 127.0(5) . . ?
C3A C4A C10A 106.6(5) . . ?
C6A C5A C4A 129.2(7) . . ?
C6A C5A H5A 115.4 . . ?
C4A C5A H5A 115.4 . . ?
C5A C6A C7A 129.9(7) . . ?
C5A C6A H6A 115.1 . . ?
C7A C6A H6A 115.1 . . ?
C8A C7A C6A 127.9(7) . . ?
C8A C7A H7A 116.1 . . ?
C6A C7A H7A 116.1 . . ?
C9A C8A C7A 130.2(7) . . ?
C9A C8A H8A 114.9 . . ?
C7A C8A H8A 114.9 . . ?
C8A C9A C10A 128.6(7) . . ?
C8A C9A H9A 115.7 . . ?
C10A C9A H9A 115.7 . . ?
C9A C10A C1A 126.0(6) . . ?
C9A C10A C4A 127.1(5) . . ?
C1A C10A C4A 106.8(5) . . ?
C6S C1S C2S 115.9(7) . . ?
C6S C1S I1S 122.1(6) . . ?
C2S C1S I1S 122.1(7) . . ?
C3S C2S F1S 118.1(8) . . ?
C3S C2S C1S 123.1(8) . . ?
F1S C2S C1S 118.8(8) . . ?
C2S C3S F2S 120.6(8) . . ?
C2S C3S C4S 121.2(7) . . ?
F2S C3S C4S 118.2(8) . . ?
C5S C4S C3S 115.7(7) . . ?
C5S C4S I2S 123.0(6) . . ?
C3S C4S I2S 121.3(6) . . ?
F3S C5S C4S 118.9(8) . . ?
F3S C5S C6S 118.1(7) . . ?
C4S C5S C6S 122.9(8) . . ?
F4S C6S C5S 119.2(8) . . ?
F4S C6S C1S 119.6(8) . . ?
C5S C6S C1S 121.2(7) . . ?
C3T C1T C2T 116.3(7) 2_575 . ?
C3T C1T I1T 122.2(6) 2_575 . ?
C2T C1T I1T 121.5(6) . . ?
F2T C2T C3T 119.7(8) . . ?
F2T C2T C1T 119.5(8) . . ?
C3T C2T C1T 120.8(7) . . ?
C2T C3T F1T 118.1(7) . . ?
C2T C3T C1T 122.9(8) . 2_575 ?
F1T C3T C1T 119.0(8) . 2_575 ?
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
C1A C2A 1.398(7) . ?
C1A C10A 1.407(6) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.400(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.401(6) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.379(6) . ?
C4A C10A 1.501(8) . ?
C5A C6A 1.362(7) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.395(6) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.391(6) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.373(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.378(6) . ?
C9A H9A 0.9300 . ?
C1S C6S 1.378(13) . ?
C1S C2S 1.397(12) . ?
C1S I1S 2.062(8) . ?
C2S C3S 1.339(13) . ?
C2S F1S 1.350(10) . ?
C3S F2S 1.346(9) . ?
C3S C4S 1.415(12) . ?
C4S C5S 1.366(11) . ?
C4S I2S 2.061(8) . ?
C5S F3S 1.354(10) . ?
C5S C6S 1.378(12) . ?
C6S F4S 1.342(9) . ?
C1T C3T 1.376(11) 2_575 ?
C1T C2T 1.385(12) . ?
C1T I1T 2.074(8) . ?
C2T F2T 1.345(9) . ?
C2T C3T 1.359(12) . ?
C3T F1T 1.360(10) . ?
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
C10A C1A C2A C3A -0.8(11) . . . . ?
C1A C2A C3A C4A -0.3(11) . . . . ?
C2A C3A C4A C5A 179.5(9) . . . . ?
C2A C3A C4A C10A 1.2(10) . . . . ?
C3A C4A C5A C6A 179.7(10) . . . . ?
C10A C4A C5A C6A -2.3(16) . . . . ?
C4A C5A C6A C7A 2.2(18) . . . . ?
C5A C6A C7A C8A -1.3(17) . . . . ?
C6A C7A C8A C9A 0.2(17) . . . . ?
C7A C8A C9A C10A 0.6(17) . . . . ?
C8A C9A C10A C1A -179.1(9) . . . . ?
C8A C9A C10A C4A -1.2(15) . . . . ?
C2A C1A C10A C9A 179.7(9) . . . . ?
C2A C1A C10A C4A 1.4(10) . . . . ?
C5A C4A C10A C9A 1.8(14) . . . . ?
C3A C4A C10A C9A -179.9(8) . . . . ?
C5A C4A C10A C1A -179.9(9) . . . . ?
C3A C4A C10A C1A -1.6(9) . . . . ?
C6S C1S C2S C3S 0.1(12) . . . . ?
I1S C1S C2S C3S 179.4(6) . . . . ?
C6S C1S C2S F1S 179.7(8) . . . . ?
I1S C1S C2S F1S -1.0(10) . . . . ?
F1S C2S C3S F2S 1.8(12) . . . . ?
C1S C2S C3S F2S -178.6(7) . . . . ?
F1S C2S C3S C4S 179.6(7) . . . . ?
C1S C2S C3S C4S -0.8(13) . . . . ?
C2S C3S C4S C5S 1.4(12) . . . . ?
F2S C3S C4S C5S 179.3(7) . . . . ?
C2S C3S C4S I2S -178.9(6) . . . . ?
F2S C3S C4S I2S -1.0(10) . . . . ?
C3S C4S C5S F3S 179.7(8) . . . . ?
I2S C4S C5S F3S 0.0(11) . . . . ?
C3S C4S C5S C6S -1.4(12) . . . . ?
I2S C4S C5S C6S 178.9(6) . . . . ?
F3S C5S C6S F4S -0.7(12) . . . . ?
C4S C5S C6S F4S -179.6(8) . . . . ?
F3S C5S C6S C1S 179.6(8) . . . . ?
C4S C5S C6S C1S 0.7(14) . . . . ?
C2S C1S C6S F4S -179.6(7) . . . . ?
I1S C1S C6S F4S 1.0(11) . . . . ?
C2S C1S C6S C5S 0.0(12) . . . . ?
I1S C1S C6S C5S -179.3(6) . . . . ?
C3T C1T C2T F2T 179.8(7) 2_575 . . . ?
I1T C1T C2T F2T -1.0(11) . . . . ?
C3T C1T C2T C3T 1.2(13) 2_575 . . . ?
I1T C1T C2T C3T -179.7(6) . . . . ?
F2T C2T C3T F1T 1.8(13) . . . . ?
C1T C2T C3T F1T -179.6(8) . . . . ?
F2T C2T C3T C1T -179.9(8) . . . 2_575 ?
C1T C2T C3T C1T -1.2(14) . . . 2_575 ?
