Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums
Cao, Hou-Ji; Wei, Xing; Sun, Fangxiang; Zhang, Xiaolei; Lu, Changsheng; Yan, Hong; Chemical Science  (2021) –; doi:10.1039/D1SC05296A

data_1565427
_publ_section_title
;
 Metal-catalyzed B--H acylmethylation of pyridylcarboranes: access to
 carborane-fused indoliziniums and quinoliziniums
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05296A
_journal_year                    2021
_chemical_formula_moiety         'C19 H27 B10 N O'
_chemical_formula_sum            'C19 H27 B10 N O'
_chemical_formula_weight         393.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2020-05-16 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                79.345(6)
_cell_angle_beta                 88.967(7)
_cell_angle_gamma                89.790(7)
_cell_formula_units_Z            12
_cell_length_a                   11.866(5)
_cell_length_b                   24.030(9)
_cell_length_c                   24.784(9)
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.24
_cell_measurement_theta_min      2.42
_cell_volume                     6944(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1707
_diffrn_reflns_av_unetI/netI     0.3003
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            64306
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_min         1.307
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8395.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1681
_refine_ls_number_reflns         31397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.3408
_refine_ls_R_factor_gt           0.0833
_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^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6765
_reflns_number_total             31397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05296a2.cif
_cod_data_source_block           5fi
_cod_depositor_comments
;

2022-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C114 H162 B60 N6 O6'
_cod_original_formula_weight         2361.09
_cod_original_formula_moiety         '6(C19 H27 B10 N O)'
_cod_original_formula_units_Z            2
_cod_database_code               1565427
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.995
_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
2.a Ternary CH refined with riding coordinates:
 C026(H026), C037(H037), C02S(H02S), C030(H030), C01P(H01P), C03N(H3AA)
2.b Secondary CH2 refined with riding coordinates:
 C01O(H01A,H01B), C04O(H04A,H04B), C053(H05A,H05B), C02C(H02B,H02C), C04I(H04H,
 H04I), C055(H05C,H05D), C03M(H03A,H03B), C04L(H04Q,H04R), C019(H01C,H01D),
 C04V(H04,H), C020(H02E,H02F), C054(H05E,H05F), C01L(H01E,H01H), C03W(H03N,
 H03O), C04Y(H2AA,HA), C01Y(H01L,H01M), C04K(H4AA,HD), C056(H05G,H05H)
2.c Aromatic/amide H refined with riding coordinates:
 C01T(H01T), C01V(H01V), C02A(H02A), C02K(H02K), C02V(H02V), C03D(H03D),
 C022(H022), C027(H027), C01Z(H01Z), C02W(H02W), C02Z(H02Z), C03H(H03H),
 C010(H010), C021(H021), C029(H029), C036(H036), C00O(H00O), C01W(H01W),
 C02H(H02H), C02L(H02L), C02O(H02O), C02P(H02P), C013(H013), C024(H024),
 C01G(H01G), C01J(H01J), C01S(H01S), C02B(H02D), C03G(H03G), C03T(H03T),
 C040(H040), C051(H051), C01F(H01F), C01I(H01I), C01N(H01N), C01Q(H01Q),
 C01U(H01U), C03F(H03M), C015(H015), C023(H023), C01E(H01K), C01X(H01X),
 C02D(H02J), C02G(H02M), C02J(H02T), C03J(H03), C016(H016), C028(H028)
2.d Idealised Me refined as rotating group:
 C041(H04C,H04D,H04E), C046(H04J,H04K,H04L), C042(H04S,H04U,H04V), C03I(H03C,
 H03E,H03F), C03A(H03I,H03J,H03L), C03C(H03Z,HB,HC)
2.e Boron cage BH refined with riding coordinates:
 B02Q(H02Q), B03R(H03R), B03V(H03V), B04C(H04F), B04E(H04G), B04M(H04M),
 B032(H032), B035(H035), B045(H045), B03S(H03S), B04A(H04N), B04J(H04O),
 B04N(H04P), B04T(H04T), B04W(H04W), B04Z(H04Z), B050(H050), B052(H052),
 B03P(H03P), B03U(H03U), B03X(H03X), B04D(H04X), B04U(H04Y), B039(H039),
 B043(H043), B047(H047), B049(H049), B02I(H02I), B02N(H02N), B02R(H02R),
 B02Y(H02Y), B03K(H03K), B04F(H0AA), B04G(H1AA), B031(H031), B038(H038),
 B01R(H01R), B02F(H02G), B02U(H02U), B03B(H03Q), B03O(H03W), B03Q(H03Y),
 B033(H033), B034(H034), B044(H044), B02T(H02X), B04B(H5AA), B04H(H6AA),
 B04P(H7AA), B04Q(H8AA), B04R(H9AA), B04S(H0BA), B04X(H1BA), B048(H048)
;
_shelx_res_checksum              66733
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'