Palladium-catalyzed B7-11 penta-arylation of the {CB<sub>11</sub>} monocarborane cluster.
Jin, Yujie; Sun, Jizeng; Zhang, Kang; Liu, Jiyong; Wörle, Michael; Duttwyler, Simon; Chemical communications (Cambridge, England) 59 (2022) 67–70; doi:10.1039/d2cc05422a

data_7131040
_publ_section_title
;
 Palladium-catalyzed B7-11 penta-arylation of the {CB<sub>11</sub>}
 monocarborane cluster.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              67
_journal_page_last               70
_journal_paper_doi               10.1039/d2cc05422a
_journal_volume                  59
_journal_year                    2022
_chemical_formula_moiety         'C37 H42 B11 O2, C8 H20 N'
_chemical_formula_sum            'C45 H62 B11 N O2'
_chemical_formula_weight         767.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-04 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   23.9942(6)
_cell_length_b                   33.9029(10)
_cell_length_c                   21.9390(7)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.124
_cell_measurement_theta_min      2.277
_cell_volume                     17846.8(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            170781
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.330
_diffrn_reflns_theta_min         2.211
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1344 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9468.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             6560
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 9810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2284
_refine_ls_number_reflns         39678
_refine_ls_number_restraints     265
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+1.8031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                28147
_reflns_number_total             39678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05422a2.cif
_cod_data_source_block           191010_jyj_133_0m_pl
_cod_depositor_comments
'Adding full bibliography for 7131036--7131040.cif.'
_cod_database_code               7131040
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N4-C179 \\sim N4-C184 \\sim N4-C182 \\sim N4-C175 \\sim N4-C176 \\sim N4-C181
\\sim N4-C177 \\sim N4-C173
 with sigma of 0.02
 C188-C175 \\sim C174-C173 \\sim C180-C179 \\sim C185-C181 \\sim C178-C177
\\sim C187-C176 \\sim C186-
 C184 \\sim C183-C182
 with sigma of 0.02
3. Restrained planarity
 C2, O9, H9, O10
 with sigma of 0.1
 C17, C18, C19, C20, C21, C22, C23
 with sigma of 0.1
 C17A, C18A, C19A, C20A, C21A, C22A, C23A
 with sigma of 0.1
 C113, O11, H11A, O12
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C23A)
Uanis(C20A) = Uanis(C20)
Uanis(C17) = Uanis(C17A)
5. Rigid body (RIGU) restrains
 C188, C174, C183, C186, C180, C185, C178, C187, C173, C182, C175, N4, C181,
 C177, C176, C179, C184
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, C20, C19, C18, C17, C22, C23, C17A, C22A, C21A, C20A, C19A, C18A, C23A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C178)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C175)=Sof(H17M)=Sof(H17N)=
 Sof(C177)=Sof(H17O)=Sof(H17P)=Sof(C181)=Sof(H18J)=Sof(H18K)=Sof(C184)=
 Sof(H18L)=Sof(H18M)=Sof(C185)=Sof(H18N)=Sof(H18O)=Sof(H18P)=Sof(C186)=
 Sof(H18Q)=Sof(H18R)=Sof(H18S)=Sof(C188)=Sof(H18W)=Sof(H18X)=Sof(H18Y)=1-FVAR(1)
 Sof(C174)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C180)=Sof(H18B)=Sof(H18C)=
 Sof(H18D)=Sof(C183)=Sof(H18E)=Sof(H18F)=Sof(H18G)=Sof(C173)=Sof(H17G)=
 Sof(H17H)=Sof(C176)=Sof(H17I)=Sof(H17J)=Sof(C179)=Sof(H17K)=Sof(H17L)=
 Sof(C182)=Sof(H18H)=Sof(H18I)=Sof(C187)=Sof(H18T)=Sof(H18U)=Sof(H18V)=FVAR(1)
 Sof(O9)=Sof(H9)=Sof(O10)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(H2A)=FVAR(2)
 Sof(O11)=Sof(H11A)=Sof(O12)=1-FVAR(3)
 Sof(O7)=Sof(H7A)=Sof(O8)=FVAR(3)
 Sof(C17A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21A)=Sof(C20A)=Sof(C19A)=
 Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(4)
 Sof(C21)=Sof(H21)=Sof(C20)=Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=Sof(C17)=
 Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C149(H14H,H14I), C151(H15E,H15F), C153(H15J,H15K), C155(H15O,H15P), C157(H15T,
 H15U), C159(H15Y,H), C161(H16G,H16H), C163(H16L,H16M), C165(H16Q,H16R),
 C167(H16V,H16W), C169(H16Z,HB), C171(H17T,H17U), C173(H17G,H17H), C176(H17I,
 H17J), C179(H17K,H17L), C182(H18H,H18I), C175(H17M,H17N), C177(H17O,H17P),
 C181(H18J,H18K), C184(H18L,H18M)
7.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C51(H51),
 C52(H52), C55(H55), C56(H56), C58(H58), C59(H59), C62(H62), C63(H63), C65(H65),
  C66(H66), C69(H69), C70(H70), C72(H72), C73(H73), C78(H78), C79(H79),
 C81(H81), C82(H82), C85(H85), C86(H86), C88(H88), C89(H89), C92(H92), C93(H93),
  C95(H95), C96(H96), C99(H99), C100(H100), C102(H102), C103(H103), C106(H106),
 C107(H107), C109(H109), C110(H110), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11),
 C12(H12), C14(H14), C15(H15), C25(H25), C26(H26), C28(H28), C29(H29), C32(H32),
  C33(H33), C35(H35), C36(H36), C21(H21), C19(H19), C18(H18), C22(H22),
 C22A(H22A), C21A(H21A), C19A(H19A), C18A(H18A), C115(H115), C116(H116),
 C118(H118), C119(H119), C122(H122), C123(H123), C125(H125), C126(H126),
 C129(H129), C130(H130), C132(H132), C133(H133), C136(H136), C137(H137),
 C139(H139), C140(H140), C143(H143), C144(H144), C146(H146), C147(H147)
7.c Fitted hexagon refined as free rotating group:
 C21(C20,C19,C18,C17,C22), C17A(C22A,C21A,C20A,C19A,C18A)
7.d Tetrahedral OH refined with riding coordinates:
 O3(H3A)
7.e Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C53(H53A,H53B,H53C), C60(H60A,H60B,H60C), C67(H67A,H67B,
 H67C), C74(H74A,H74B,H74C), C83(H83A,H83B,H83C), C90(H90A,H90B,H90C), C97(H97A,
 H97B,H97C), C104(H10A,H10B,H10C), C111(H11B,H11C,H11D), C150(H15B,H15C,H15D),
 C152(H15G,H15H,H15I), C154(H15L,H15M,H15N), C156(H15Q,H15R,H15S), C158(H15V,
 H15W,H15X), C160(H16D,H16E,H16F), C162(H16I,H16J,H16K), C164(H16N,H16O,H16P),
 C166(H16S,H16T,H16U), C168(H16X,H16Y,HA), C170(H17Q,H17R,H17S), C172(H17V,H17W,
 H17X), C174(H17A,H17B,H17C), C178(H17D,H17E,H17F), C180(H18B,H18C,H18D),
 C183(H18E,H18F,H18G), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C30(H30A,H30B,
 H30C), C37(H37A,H37B,H37C), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F),
 C120(H12A,H12B,H12C), C127(H12D,H12E,H12F), C134(H13A,H13B,H13C), C141(H14A,
 H14B,H14C), C148(H14D,H14E,H14F), C185(H18N,H18O,H18P), C186(H18Q,H18R,H18S),
 C187(H18T,H18U,H18V), C188(H18W,H18X,H18Y)
7.f Idealised tetrahedral OH refined as rotating group:
 O5(H5B), O2(H2A), O9(H9), O7(H7A), O11(H11A)
7.g Boron cage BH refined with riding coordinates:
 C38(H38A), B12(H12G), B13(H13), B14(H14G), B15(H15A), B16(H16), C75(H75),
 B23(H23), B24(H24), B25(H25A), B26(H26A), B27(H27), C1(H1), B1(H1A), B2(H2),
 B3(H3), B4(H4A), B5(H5A), C112(H112), B34(H34), B35(H35A), B36(H36A), B37(H37),
  B38(H38)
;
_shelx_res_checksum              703
_shelx_hkl_checksum              5708
_olex2_submission_special_instructions 'No special instructions were received'