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_7058234
_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 rmad
_chemical_formula_moiety         'C22 H16 F8 I2 O4, C10 H8 N4'
_chemical_formula_sum            'C32 H24 F8 I2 N4 O4'
_chemical_formula_weight         934.35
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-29
_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                68.135(8)
_cell_angle_beta                 70.540(8)
_cell_angle_gamma                69.104(7)
_cell_formula_units_Z            2
_cell_length_a                   10.4002(10)
_cell_length_b                   13.3883(13)
_cell_length_c                   14.2970(14)
_cell_measurement_reflns_used    84467
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.68
_cell_measurement_theta_min      2.15
_cell_volume                     1679.3(3)
_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
'X-Area Integrate 1.72.0.0 (STOE, 2018) X-Area X-Red32 1.63.4.0 (STOE, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      119.99
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44176
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         2.154
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  0.7170
_exptl_absorpt_correction_T_min  0.3572
_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    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 / heptane'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.559
_refine_diff_density_min         -1.765
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         17211
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0972P)^2^+1.7781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                16177
_reflns_number_total             17217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj05750h2.cif
_cod_data_source_block           apy_1b
_cod_depositor_comments
'Adding full bibliography for 7058234--7058236.cif.'
_cod_database_code               7058234
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.493
_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), C9(H9), C40(H40), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C39(H39A,H39B), C42(H42A,H42B), C50(H50A,H50B),
  C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31),
 C32(H32), C56(H56), C57(H57), C58(H58), C59(H59), C61(H61), C62(H62), C63(H63),
  C64(H64)
;