Aqueous hydroboration of alkynes via nonclassical generation of N-heterocyclic carbenes
Tao, Sheng; Wang, Yang; Pan, Qianxiu; Zhao, Jixing; Bu, Qingqing; Chen, Fei; Liu, Jichang; Dai, Bin; Wei, Donghui; Liu, Ning; Green Chemistry 25 (2023) 6704–6716; doi:10.1039/D3GC01232H

data_7247094
_publ_section_title
;
 Aqueous hydroboration of alkynes via nonclassical generation of
 N-heterocyclic carbenes
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6704
_journal_page_last               6716
_journal_paper_doi               10.1039/D3GC01232H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C27 H39 B2 N3 O4'
_chemical_formula_sum            'C27 H39 B2 N3 O4'
_chemical_formula_weight         491.23
_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     dual
_audit_creation_date             2022-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-09 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                88.955(2)
_cell_angle_beta                 88.529(2)
_cell_angle_gamma                76.813(3)
_cell_formula_units_Z            8
_cell_length_a                   11.5388(5)
_cell_length_b                   15.2170(7)
_cell_length_c                   31.3898(14)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.84
_cell_measurement_theta_min      3.28
_cell_volume                     5364.1(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      173.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21455
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         2.816
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 146677 reflections, Rint = 0.1155
 (51190 with I > 3sig(I), Rint = 0.0851)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1355
_refine_ls_number_reflns         21455
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0966
_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^)+(0.1498P)^2^+4.2067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14189
_reflns_number_total             21455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc01232h2.cif
_cod_data_source_block           20220506_ts3_0m_5
_cod_depositor_comments          'Adding full bibliography for 7247094.cif.'
_cod_database_code               7247094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.842
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5332(19)
 0.4668(19)
2. 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
3. Restrained distances
 C26A-C27A = C27-C26 = C26A-C25 = C26-C25
 1.53 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C26A \\sim C27 \\sim C27A: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(C27) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27D)=
 Sof(H27E)=Sof(H27F)=1-FVAR(1)
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=
 Sof(H27C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C25(H25C,H25D), C26(H26A,H26B), C26A(H26C,H26D), C79(H79A,
 H79B), C80(H80A,H80B), C106(H10D,H10E), C107(H10F,H10G), C52(H52A,H52B),
 C53(H53A,H53B)
6.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23),
 C24(H24), C68(H68), C69(H69), C70(H70), C71(H71), C75(H75), C76(H76), C77(H77),
  C78(H78), C95(H95), C96(H96), C97(H97), C98(H98), C102(H102), C103(H103),
 C104(H104), C105(H105), C41(H41), C42(H42), C43(H43), C44(H44), C48(H48),
 C49(H49), C50(H50), C51(H51)
6.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C9(H9A,
 H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C27(H27A,H27B,H27C), C27A(H27D,H27E,H27F), C56(H56A,H56B,H56C), C57(H57A,H57B,
 H57C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C63(H63A,H63B,H63C), C64(H64A,
 H64B,H64C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C81(H81A,H81B,H81C),
 C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C86(H86A,H86B,H86C), C87(H87A,H87B,
 H87C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C), C93(H93A,H93B,H93C), C94(H94A,
 H94B,H94C), C108(H10H,H10I,H10J), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C),
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              79377
_shelx_hkl_checksum              10072
_olex2_submission_special_instructions 'No special instructions were received'