Synthesis of tetra-pincer nickel(ii) and palladium(ii) complexes of resorcin[4]arene-octophosphinite [Res(OPR<sub>2</sub>)<sub>8</sub>] and rhodium-catalyzed regioselective hydroformylation reaction.
Ananthnag, Guddekoppa S.; Mondal, Dipanjan; Mague, Joel T.; Balakrishna, Maravanji S.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 14632–14641; doi:10.1039/c9dt02499a

data_7700831
_publ_section_title
;
 Synthesis of tetra-pincer nickel(ii) and palladium(ii) complexes of
 resorcin[4]arene-octophosphinite [Res(OPR<sub>2</sub>)<sub>8</sub>] and
 rhodium-catalyzed regioselective hydroformylation reaction.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14632
_journal_page_last               14641
_journal_paper_doi               10.1039/c9dt02499a
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C140 H124 Br4 O8 P8 Pd4'
_chemical_formula_sum            'C140 H124 Br4 O8 P8 Pd4'
_chemical_formula_weight         2927.38
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.2120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.9334(7)
_cell_length_b                   21.8518(4)
_cell_length_c                   26.0254(5)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      66.692
_cell_measurement_theta_min      2.814
_cell_volume                     14488.4(5)
_computing_data_collection       '<i>APEX2</i> (Bruker, 2014)'
_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    '<i>SHELXT</i> (Bruker, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku saturn 724'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            52249
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         67.036
_diffrn_reflns_theta_min         2.664
_exptl_absorpt_coefficient_mu    6.464
_exptl_absorpt_correction_T_max  0.57
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '<i>SADABS</i> (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             5888
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.097
_refine_diff_density_max         1.728
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     716
_refine_ls_number_reflns         12664
_refine_ls_number_restraints     626
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1260P)^2^+80.9627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2276
_refine_ls_wR_factor_ref         0.2740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6859
_reflns_number_total             12664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02499a2.cif
_cod_data_source_block           msb608b
_cod_depositor_comments
'Adding full bibliography for 7700830--7700831.cif.'
_cod_database_code               7700831
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.573
_shelx_estimated_absorpt_t_min   0.521
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C56, C56A}
3. Restrained distances
 P1-C1 \\sim P1-C1A
 with sigma of 0.02
 P1-C7 \\sim P1-C7A
 with sigma of 0.02
 P2-C19 \\sim P2-C19A
 with sigma of 0.02
 P2-C25 \\sim P2-C25A
 with sigma of 0.02
 P3-C48 \\sim P3-C48A
 with sigma of 0.02
 C57-C58 \\sim C57A-C58A
 with sigma of 0.02
 C56-C57 \\sim C56A-C57A
 with sigma of 0.02
 C56-C58 \\sim C56A-C58A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A)
\\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq,
Uanis(C6A) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim
Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C7A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C21A) \\sim Ueq,
Uanis(C22A) \\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C26A)
\\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C30A) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq,
Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47)
\\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50) \\sim Ueq,
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C48A)
\\sim Ueq, Uanis(C49A) \\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C51A) \\sim Ueq,
Uanis(C52A) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C55)
\\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C58) \\sim Ueq,
Uanis(C56A) \\sim Ueq, Uanis(C57A) \\sim Ueq, Uanis(C58A) \\sim Ueq, Uanis(C59)
\\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C62) \\sim Ueq,
Uanis(C63) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C69) \\sim Ueq,
Uanis(C70) \\sim Ueq: with sigma of 0.007 and sigma for terminal atoms of 0.014
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
Uanis(C8) = Uanis(C8A)
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
Uanis(C27) = Uanis(C27A)
Uanis(C28) = Uanis(C28A)
Uanis(C29) = Uanis(C29A)
Uanis(C30) = Uanis(C30A)
Uanis(C48) = Uanis(C48A)
Uanis(C49) = Uanis(C49A)
Uanis(C50) = Uanis(C50A)
Uanis(C51) = Uanis(C51A)
Uanis(C52) = Uanis(C52A)
Uanis(C53) = Uanis(C53A)
Uanis(C56) = Uanis(C56A)
Uanis(C57) = Uanis(C57A)
Uanis(C58) = Uanis(C58A)
5. Others
 Sof(H55C)=Sof(H55D)=Sof(C56A)=Sof(H56C)=Sof(H56D)=Sof(C57A)=Sof(H57C)=
 Sof(H57D)=Sof(C58A)=Sof(H58D)=Sof(H58E)=Sof(H58F)=1-FVAR(1)
 Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(C57)=Sof(H57A)=Sof(H57B)=
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(1)
 Fixed Sof: C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5)
 H5(0.5) C6(0.5) H6(0.5) C1A(0.5) C2A(0.5) H2A(0.5) C3A(0.5) H3A(0.5) C4A(0.5)
 H4A(0.5) C5A(0.5) H5A(0.5) C6A(0.5) H6A(0.5) C7(0.5) C8(0.5) H8(0.5) C9(0.5)
 H9(0.5) C10(0.5) H10(0.5) C11(0.5) H11(0.5) C12(0.5) H12(0.5) C7A(0.5)
 C8A(0.5) H8A(0.5) C9A(0.5) H9A(0.5) C10A(0.5) H10A(0.5) C11A(0.5) H11A(0.5)
 C12A(0.5) H12A(0.5) C19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5)
 H22(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5) C19A(0.5) C20A(0.5) H20A(0.5)
 C21A(0.5) H21A(0.5) C22A(0.5) H22A(0.5) C23A(0.5) H23A(0.5) C24A(0.5)
 H24A(0.5) C25(0.5) C26(0.5) H26(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5)
 C29(0.5) H29(0.5) C30(0.5) H30(0.5) C25A(0.5) C26A(0.5) H26A(0.5) C27A(0.5)
 H27A(0.5) C28A(0.5) H28A(0.5) C29A(0.5) H29A(0.5) C30A(0.5) H30A(0.5) C48(0.5)
 C49(0.5) H49(0.5) C50(0.5) H50(0.5) C51(0.5) H51(0.5) C52(0.5) H52(0.5)
 C53(0.5) H53(0.5) C48A(0.5) C49A(0.5) H49A(0.5) C50A(0.5) H50A(0.5) C51A(0.5)
 H51A(0.5) C52A(0.5) H52A(0.5) C53A(0.5) H53A(0.5)
6.a Ternary CH refined with riding coordinates:
 C31(H31), C54(H54)
6.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C55(H55A,H55B), C55(H55C,
 H55D), C56(H56A,H56B), C57(H57A,H57B), C56A(H56C,H56D), C57A(H57C,H57D)
6.c Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C58(H58A,H58B,H58C), C58A(H58D,H58E,H58F)
6.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C4A(H4A),
 C5A(H5A), C6A(H6A), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C8A(H8A),
 C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C16(H16), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A),
 C24A(H24A), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C26A(H26A),
 C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A), C39(H39), C43(H43), C44(H44),
 C45(H45), C46(H46), C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53),
  C49A(H49A), C50A(H50A), C51A(H51A), C52A(H52A), C53A(H53A), C60(H60),
 C61(H61), C62(H62), C63(H63), C64(H64), C66(H66), C67(H67), C68(H68), C69(H69),
  C70(H70)
6.e Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C1A(C2A,C3A,C4A,C5A,C6A), C7(C8,C9,C10,C11,C12), C7A(C8A,
 C9A,C10A,C11A,C12A), C19(C20,C21,C22,C23,C24), C19A(C20A,C21A,C22A,C23A,C24A),
 C25(C26,C27,C28,C29,C30), C25A(C26A,C27A,C28A,C29A,C30A), C48(C49,C50,C51,C52,
 C53), C48A(C49A,C50A,C51A,C52A,C53A)
;
_shelx_res_checksum              74570
_shelx_fab_checksum              74747
_olex2_submission_special_instructions 'No special instructions were received'