The halogen bonding proclivity of the ortho-methoxy–hydroxy group in cocrystals of o-vanillin imines and diiodotetrafluoro-benzenes
Zbačnik, Marija; Pajski, Matea; Stilinović, Vladimir; Vitković, Matea; Cinčić, Dominik; CrystEngComm  (2017) –; doi:10.1039/C7CE01332A

data_7229085
_publ_section_title
;
 The halogen bonding proclivity of the ortho-methoxy--hydroxy group in
 cocrystals of o-vanillin imines and diiodotetrafluoro-benzenes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01332A
_journal_year                    2017
_chemical_formula_moiety         (C18H15NO2)(C6F4I2)
_chemical_formula_sum            'C24 H15 F4 I2 N O2'
_chemical_formula_weight         679.17
_chemical_name_common
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,4-diiodotetrafluorobenzene)
_chemical_name_systematic
(2-Methoxy-6-(naphthalen-1-yliminomethyl)-phenol)(1,4-diiodotetrafluorobenzene)
_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_method           SHELXL-2014/7
_audit_update_record
;
2017-06-27 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.744(3)
_cell_angle_beta                 103.077(4)
_cell_angle_gamma                107.441(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6601(3)
_cell_length_b                   12.7245(5)
_cell_length_c                   13.2834(6)
_cell_measurement_reflns_used    6465
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      38.6689
_cell_measurement_theta_min      3.8615
_cell_volume                     1169.04(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14644
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         3.867
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark
and Ried (1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.156
_refine_diff_density_max         1.052
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0463
_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/[\s^2^(Fo^2^)+(0.0763P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2871
_reflns_number_total             4964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01332a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7229085
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              15895