Induction of chirality in 4,4′-azopyridine by halogen-bonding interaction with optically active ditopic donors
Alfuth, Jan; Chojnacki, Jarosław; Połoński, Tadeusz; Olszewska, Teresa; New Journal of Chemistry 43 (2019) 5512–; doi:10.1039/C8NJ05750H

data_7058236
_publ_section_title
;
 Induction of chirality in 4,4&#x2032;-azopyridine by halogen-bonding
 interaction with optically active ditopic donors
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5512
_journal_paper_doi               10.1039/C8NJ05750H
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 F8 I2 O2, C10 H8 N4'
_chemical_formula_sum            'C30 H22 F8 I2 N4 O2'
_chemical_formula_weight         876.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-17 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2031(2)
_cell_length_b                   17.8566(4)
_cell_length_c                   32.8945(8)
_cell_measurement_reflns_used    34384
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.28
_cell_volume                     3056.22(15)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction        'STOE X-Area'
_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      119.99
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            38579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.254
_diffrn_reflns_theta_min         2.180
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.316
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Flack x determined using 2672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0523P)^2^+1.1536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6979
_reflns_number_total             8255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj05750h2.cif
_cod_data_source_block           apy_2
_cod_depositor_comments
'Adding full bibliography for 7058234--7058236.cif.'
_cod_database_code               7058236
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30)
;