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_1554749
_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 rmad
_chemical_formula_moiety         'C152 H120 N8 Pd2, 4(B F4)'
_chemical_formula_sum            'C152 H120 B4 F16 N8 Pd2'
_chemical_formula_weight         2618.59
_space_group_crystal_system      tetragonal
_space_group_IT_number           94
_space_group_name_Hall           'P 4n 2n'
_space_group_name_H-M_alt        'P 42 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-17
_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            4
_cell_length_a                   32.9899(5)
_cell_length_b                   32.9899(5)
_cell_length_c                   14.3593(4)
_cell_measurement_reflns_used    10273
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      70.8100
_cell_measurement_theta_min      2.6500
_cell_volume                     15627.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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 -106.00 -19.00 0.75 30.00 -- -41.90 -19.00 -90.00 116 2 \w -73.00 5.00 0.75 30.00 -- -41.90 77.00 -90.00 104 3 \w 30.00 120.00 0.75 140.00 -- 105.08 -30.00 30.00 120 4 \w 97.00 177.25 0.75 140.00 -- 105.08 125.00 120.00 107 5 \w 81.00 174.00 0.75 140.00 -- 105.08 30.00-150.00 124 6 \w 23.00 108.50 0.75 140.00 -- 105.08 -94.00 60.00 114'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184952000
_diffrn_orient_matrix_UB_12      -0.0244807000
_diffrn_orient_matrix_UB_13      -0.0808612000
_diffrn_orient_matrix_UB_21      0.0428154000
_diffrn_orient_matrix_UB_22      0.0088834000
_diffrn_orient_matrix_UB_23      0.0376148000
_diffrn_orient_matrix_UB_31      -0.0019209000
_diffrn_orient_matrix_UB_32      -0.0387948000
_diffrn_orient_matrix_UB_33      0.0596163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            48137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.748
_diffrn_reflns_theta_max         66.748
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89203
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_description       plate
_exptl_crystal_F_000             5376
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.233
_refine_diff_density_min         -1.572
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 3713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     806
_refine_ls_number_reflns         13861
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0861
_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^)+(0.1945P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2445
_refine_ls_wR_factor_ref         0.2598
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                10932
_reflns_number_total             13861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00155g2.cif
_cod_data_source_block           '[Pd2_(Rp)-5_4_BF4_4'
_cod_original_cell_volume        15627.7(6)
_cod_database_code               1554749
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H24 N1 Pd1 P1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 B2-F7
 1.32 with sigma of 0.01
 F9-B2
 1.32 with sigma of 0.01
 B2-F8
 1.32 with sigma of 0.01
 F9-F8
 2 with sigma of 0.01
 B1-F5
 1.32 with sigma of 0.001
 F3-B1
 1.32 with sigma of 0.001
 B2-F6
 1.32 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C52)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed U11: F5(0.20501) F6(0.12169) F7(0.23311) F8(0.2241)
 Fixed U22: F3(0.25238) F5(0.20222) F6(0.19811) F7(0.2) F8(0.2) B2(0.21377)
 Fixed U33: F5(0.21167) F6(0.18897) F7(0.18818) F8(0.22806)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C26(H26A,H26B), C27(H27A,H27B), C67(H67A,
 H67B), C68(H68A,H68B), C75(H75A,H75B), C76(H76A,H76B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C21(H21), C22(H22), C24(H24), C28(H28), C29(H29), C30(H30),
  C32(H32), C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40),
 C41(H41), C43(H43), C45(H45), C46(H46), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52), C54(H54), C56(H56), C57(H57), C59(H59), C60(H60), C62(H62),
 C64(H64), C65(H65), C70(H70), C71(H71), C73(H73)
;
_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.769