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_1554750
_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_formula_moiety
'2(C130 H112 N4 P4 Pd2), 8(C F3 O3 S), 3(C4 H8 O)'
_chemical_formula_sum            'C280 H248 F24 N8 O27 P8 Pd4 S8'
_chemical_formula_weight         5542.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                 97.750(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   46.6905(8)
_cell_length_b                   26.3232(3)
_cell_length_c                   31.9982(5)
_cell_measurement_reflns_used    34893
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.0900
_cell_measurement_theta_min      2.4150
_cell_volume                     38968.0(10)
_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    'ShelXT (Sheldrick, 2015)'
_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 -68.00 29.00 1.00 7.50 -- -41.78 57.00 30.00 97 2 \w -109.00 -22.00 1.00 7.50 -- -41.78 -57.00 120.00 87 3 \w -69.00 30.00 1.00 7.50 -- -41.78 57.00 -90.00 99 4 \w -95.00 -4.00 1.00 7.50 -- -41.78 125.00 30.00 91 5 \w 33.00 109.00 1.00 45.00 -- 112.00 -94.00 -90.00 76 6 \w 47.00 116.00 1.00 45.00 -- 112.00-111.00-180.00 69 7 \w 45.00 140.00 1.00 45.00 -- 112.00 -30.00-150.00 95 8 \w 43.00 93.00 1.00 45.00 -- 112.00 -61.00 -60.00 50 9 \w 36.00 136.00 1.00 45.00 -- 112.00 -30.00 30.00 100 10 \w 105.00 141.00 1.00 45.00 -- 112.00 -61.00 -60.00 36 11 \w 88.00 177.00 1.00 45.00 -- 112.00 45.00 30.00 89 12 \w 104.00 178.00 1.00 45.00 -- 112.00 111.00 -30.00 74 13 \w 61.00 136.00 1.00 45.00 -- 112.00 -77.00 0.00 75'
_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      -0.0201519000
_diffrn_orient_matrix_UB_12      0.0410117000
_diffrn_orient_matrix_UB_13      -0.0219722000
_diffrn_orient_matrix_UB_21      -0.0237668000
_diffrn_orient_matrix_UB_22      -0.0403072000
_diffrn_orient_matrix_UB_23      -0.0111917000
_diffrn_orient_matrix_UB_31      -0.0118016000
_diffrn_orient_matrix_UB_32      0.0108273000
_diffrn_orient_matrix_UB_33      0.0418323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            109627
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         2.305
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018) 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    0.945
_exptl_crystal_description       plate
_exptl_crystal_F_000             11392
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.079
_refine_diff_density_max         4.275
_refine_diff_density_min         -1.553
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1732
_refine_ls_number_reflns         34510
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0815
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1935P)^2^+33.9101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.2681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                25716
_reflns_number_total             34510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00155g2.cif
_cod_data_source_block           Pd2_dppp2_(rac)-4_2_OTf_4
_cod_database_code               1554750
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H40 N2 O3 Pd2 P2 S1 F3'
_chemical_oxdiff_usercomment     'THF+ MeOH + DCM + ACN and CP'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C145-S2
 1.83 with sigma of 0.01
 C146-S1
 1.83 with sigma of 0.01
 C145-F4
 1.39 with sigma of 0.01
 C145-F5
 1.39 with sigma of 0.01
 C146-F6
 1.39 with sigma of 0.01
 F1-C146
 1.39 with sigma of 0.01
 F8-C144
 1.39 with sigma of 0.01
 C144-F9
 1.39 with sigma of 0.01
 C144-F8
 1.39 with sigma of 0.01
 C144-F7
 1.39 with sigma of 0.01
 C135-C134
 1.54 with sigma of 0.01
 C133-C132
 1.54 with sigma of 0.01
 C134-C133
 1.54 with sigma of 0.01
 C140-O16
 1.43 with sigma of 0.01
 C142-C141
 1.54 with sigma of 0.02
 C141-C140
 1.54 with sigma of 0.02
 C142-C143
 1.54 with sigma of 0.02
 C139-O18
 1.43 with sigma of 0.01
 C136-C137
 1.54 with sigma of 0.01
 C137-C138
 1.54 with sigma of 0.01
 C138-C139
 1.54 with sigma of 0.01
 O8-S5
 1.43 with sigma of 0.001
 S5-O7
 1.43 with sigma of 0.001
 O9-S5
 1.48 with sigma of 0.001
 C144-S5
 1.83 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C136) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C138) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.01
Uanis(C145) \\sim Ueq, Uanis(C146) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C144) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
Uanis(C134) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C133) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(S5) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(O16) = Uanis(C140) = Uanis(C141) = Uanis(C142) = Uanis(C143)
4. Others
 Fixed Sof: S1(0.5) S2(0.5) F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5)
 O1(0.5) O2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5) O16(0.5) O17(0.5) O18(0.5)
 C132(0.5) H13I(0.5) H13J(0.5) C133(0.5) H13K(0.5) H13L(0.5) C134(0.5)
 H13M(0.5) H13N(0.5) C135(0.5) H13O(0.5) H13P(0.5) C136(0.5) H13A(0.5)
 H13B(0.5) C137(0.5) H13C(0.5) H13D(0.5) C138(0.5) H13E(0.5) H13F(0.5)
 C139(0.5) H13G(0.5) H13H(0.5) C140(0.5) H14A(0.5) H14B(0.5) C141(0.5)
 H14C(0.5) H14D(0.5) C142(0.5) H14E(0.5) H14F(0.5) C143(0.5) H14G(0.5)
 H14H(0.5) C145(0.5) C146(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C26(H26A,H26B), C27(H27A,H27B), C56(H56A,
 H56B), C57(H57A,H57B), C64(H64A,H64B), C65(H65A,H65B), C89(H89A,H89B),
 C90(H90A,H90B), C91(H91A,H91B), C117(H11A,H11B), C118(H11C,H11D), C119(H11E,
 H11F), C132(H13I,H13J), C133(H13K,H13L), C134(H13M,H13N), C135(H13O,H13P),
 C136(H13A,H13B), C137(H13C,H13D), C138(H13E,H13F), C139(H13G,H13H), C140(H14A,
 H14B), C141(H14C,H14D), C142(H14E,H14F), C143(H14G,H14H)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C32(H32),
  C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
 C42(H42), C43(H43), C45(H45), C46(H46), C48(H48), C49(H49), C51(H51), C53(H53),
  C54(H54), C60(H60), C62(H62), C63(H63), C67(H67), C68(H68), C70(H70),
 C71(H71), C73(H73), C74(H74), C75(H75), C76(H76), C77(H77), C78(H78), C79(H79),
  C80(H80), C81(H81), C83(H83), C84(H84), C85(H85), C86(H86), C87(H87),
 C93(H93), C94(H94), C95(H95), C96(H96), C97(H97), C99(H99), C100(H100),
 C102(H102), C103(H103), C104(H104), C106(H106), C107(H107), C108(H108),
 C109(H109), C110(H110), C112(H112), C113(H113), C114(H114), C115(H115),
 C116(H116), C121(H121), C122(H122), C123(H123), C124(H124), C125(H125),
 C127(H127), C128(H128), C129(H129), C130(H130), C131(H131)
;
_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 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.717