Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands
Anhäuser, J.; Puttreddy, R.; Lorenz, Y.; Schneider, A.; Engeser, M.; Rissanen, K.; Lützen, A.; Organic Chemistry Frontiers 6 (2019) 1226–; doi:10.1039/C9QO00155G

data_1554748
_publ_section_title
;
 Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine)
 ligands
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1226
_journal_paper_doi               10.1039/C9QO00155G
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'I3, C38 H31 N2, C2 H3 N'
_chemical_formula_sum            'C40 H34 I3 N3'
_chemical_formula_weight         937.40
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-01-20
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-28 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            8
_cell_length_a                   13.41045(10)
_cell_length_b                   13.41045(10)
_cell_length_c                   40.0935(5)
_cell_measurement_reflns_used    29996
_cell_measurement_temperature    120.00(16)
_cell_measurement_theta_max      28.0980
_cell_measurement_theta_min      1.8780
_cell_volume                     7210.42(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
'List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -39.00 46.50 0.75 30.00 -- -18.14 57.00 -90.00 114 2 \w -41.00 43.00 0.75 30.00 -- -18.14 77.00 150.00 112 3 \w -42.00 43.50 0.75 30.00 -- -18.14 77.00 -30.00 114 4 \w 0.00 79.50 0.75 30.00 -- 19.23 57.00 150.00 106 5 \w 2.00 86.00 0.75 30.00 -- 19.23 57.00-120.00 112 6 \w -20.00 61.00 0.75 30.00 -- 19.23 -99.00 90.00 108 7 \w -2.00 71.50 0.75 30.00 -- 19.23 57.00 -30.00 98 8 \w -5.00 80.50 0.75 30.00 -- 19.23 77.00 30.00 114'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0063168000
_diffrn_orient_matrix_UB_12      -0.0177959000
_diffrn_orient_matrix_UB_13      -0.0165270000
_diffrn_orient_matrix_UB_21      -0.0391754000
_diffrn_orient_matrix_UB_22      0.0315433000
_diffrn_orient_matrix_UB_23      -0.0054961000
_diffrn_orient_matrix_UB_31      0.0349800000
_diffrn_orient_matrix_UB_32      0.0385127000
_diffrn_orient_matrix_UB_33      -0.0031381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            99031
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.060
_diffrn_reflns_theta_min         2.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.633
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_description       block
_exptl_crystal_F_000             3632
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.068
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
;
 Flack x determined using 3012 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         9148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+33.3103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                8071
_reflns_number_total             9148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00155g2.cif
_cod_data_source_block           (Rp)-4
_cod_original_cell_volume        7210.41(14)
_cod_database_code               1554748
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N2 I2'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14),
  C15(H15), C17(H17), C21(H21), C22(H22), C25(H25), C29(H29), C30(H30),
 C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.876