Zinc borylation and reduction by a diborane(4) species <i>via</i> B-O bond formation.
Griffin, Liam P.; Aldridge, Simon; Chemical science 15 (2024) 19577–19582; doi:10.1039/d4sc06389a

data_1573069
_publ_section_title
;
 Zinc borylation and reduction by a diborane(4) species <i>via</i> B-O
 bond formation.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              19577
_journal_page_last               19582
_journal_paper_doi               10.1039/d4sc06389a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C49 H65 B N4 O Zn'
_chemical_formula_sum            'C49 H65 B N4 O Zn'
_chemical_formula_weight         802.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-19 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1404(2)
_cell_length_b                   15.15920(10)
_cell_length_c                   19.0592(2)
_cell_measurement_reflns_used    40686
_cell_measurement_temperature    149.98(11)
_cell_measurement_theta_max      76.3230
_cell_measurement_theta_min      3.6890
_cell_volume                     4570.87(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5035
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -40.00  27.00   1.00    1.50    --  -41.77  57.00  90.00   67
  2  \w    -20.00  31.00   1.00    1.50    --  -41.77  37.00 -30.00   51
  3  \w      2.00  33.00   1.00    1.50    --  -41.77  19.00-150.00   31
  4  \w      7.00  37.00   1.00    1.50    --  -41.77  19.00-180.00   30
  5  \w     46.00  83.00   1.00    1.50    --   41.77-125.00 -30.00   37
  6  \w     24.00  59.00   1.00    1.50    --   41.77  57.00  60.00   35
  7  \w     41.00  71.00   1.00    6.00    --  111.00 -45.00 150.00   30
  8  \w     49.00  75.00   1.00    6.00    --  111.00 -61.00 -60.00   26
  9  \w     41.00  72.00   1.00    6.00    --  111.00 -45.00 120.00   31
 10  \w    101.00 127.00   1.00    6.00    --  111.00  30.00-120.00   26
 11  \w     98.00 130.00   1.00    6.00    --  111.00  45.00  30.00   32
 12  \w    147.00 173.00   1.00    6.00    --  111.00  45.00  30.00   26
 13  \w     54.00 106.00   1.00    6.00    --  111.00-111.00  90.00   52
 14  \w     90.00 150.00   1.00    6.00    --  111.00  45.00 -90.00   60
 15  \w     42.00  68.00   1.00    6.00    --  111.00 -45.00 -60.00   26
 16  \w     45.00  70.00   1.00    6.00    --  111.00 -45.00-180.00   25
 17  \w     59.00  91.00   1.00    6.00    --  111.00 -61.00  30.00   32
 18  \w     60.00  97.00   1.00    6.00    --  111.00-111.00  60.00   37
 19  \w     43.00  72.00   1.00    6.00    --  111.00 -45.00  60.00   29
 20  \w     40.00 100.00   1.00    6.00    --  111.00-111.00 -30.00   60
 21  \w     63.00  92.00   1.00    6.00    --  111.00 -94.00 -30.00   29
 22  \w    149.00 178.00   1.00    6.00    --  111.00  30.00-120.00   29
 23  \w     41.00  71.00   1.00    6.00    --  111.00 -45.00   0.00   30
 24  \w     43.00 108.00   1.00    6.00    --  111.00-111.00  30.00   65
 25  \w    131.00 172.00   1.00    6.00    --  111.00  77.00  90.00   41
 26  \w     41.00  72.00   1.00    6.00    --  111.00 -45.00  90.00   31
 27  \w     11.00  37.00   1.00    1.50    --  -41.77  19.00 150.00   26
 28  \w      0.00  26.00   1.00    1.50    --  -41.77  19.00-120.00   26
 29  \w     -4.00  21.00   1.00    1.50    --  -41.77  19.00 -90.00   25
 30  \w    -20.00  18.00   1.00    1.50    --  -41.77  37.00 -60.00   38
 31  \w     50.00  76.00   1.00    1.50    --   41.77 -99.00  90.00   26
 32  \w     35.00  77.00   1.00    1.50    --   41.77-125.00-120.00   42
 33  \w     24.00  50.00   1.00    1.50    --   41.77  57.00  30.00   26
 34  \w    117.00 162.00   1.00    6.00    --  111.00  77.00-180.00   45
 35  \w     74.00 106.00   1.00    6.00    --  111.00-111.00 150.00   32
 36  \w    100.00 177.00   1.00    6.00    --  111.00  30.00 150.00   77
 37  \w     87.00 117.00   1.00    6.00    --  111.00  30.00-150.00   30
 38  \w    126.00 152.00   1.00    6.00    --  111.00  30.00-150.00   26
 39  \w    142.00 168.00   1.00    6.00    --  111.00  45.00 120.00   26
 40  \w     67.00 109.00   1.00    6.00    --  111.00-111.00-180.00   42
 41  \w     40.00  65.00   1.00    6.00    --  111.00 -45.00-120.00   25
 42  \w    110.00 168.00   1.00    6.00    --  111.00 111.00-120.00   58
 43  \w     54.00  92.00   1.00    6.00    --  111.00 -61.00-150.00   38
 44  \w    118.00 161.00   1.00    6.00    --  111.00  30.00   0.00   43
 45  \w     78.00 109.00   1.00    6.00    --  111.00-111.00 120.00   31
 46  \w     60.00  99.00   1.00    6.00    --  111.00 -91.00-141.00   39
 47  \w     47.00  75.00   1.00    6.00    --  111.00-111.00 120.00   28
 48  \w     83.00 109.00   1.00    6.00    --  111.00-111.00-120.00   26
 49  \w     83.00 109.00   1.00    6.00    --  111.00-111.00   0.00   26
 50  \w     84.00 109.00   1.00    6.00    --  111.00-111.00  60.00   25
 51  \w     91.00 117.00   1.00    6.00    --  111.00  61.00-150.00   26
 52  \w    130.00 177.00   1.00    6.00    --  111.00  61.00-150.00   47
 53  \w     73.00 109.00   1.00    6.00    --  111.00-111.00 -60.00   36
 54  \w     63.00 109.00   1.00    6.00    --  111.00-111.00-150.00   46
 55  \w     -3.00  22.00   1.00    1.50    --   34.00  92.00 -92.49   25
 56  \w   -111.00 -19.00   1.00    1.50    --  -41.77 -37.00 150.00   92
 57  \w    -46.00 -19.00   1.00    1.50    --  -41.77 -37.00 -90.00   27
 58  \w    -73.00 -24.00   1.00    1.50    --  -41.77  77.00  60.00   49
 59  \w    -98.00 -47.00   1.00    1.50    --  -41.77 -37.00 -90.00   51
 60  \w     13.00  39.00   1.00    1.50    --   46.00  82.00 -48.65   26
 61  \w     14.00  39.00   1.00    1.50    --   46.00  81.00  34.87   25
 62  \w     13.00  40.00   1.00    1.50    --   46.00  82.00-163.50   27
 63  \w     15.00  41.00   1.00    1.50    --   46.00  82.00 110.50   26
 64  \w     89.00 115.00   1.00    1.50    --   58.00  70.00-178.88   26
 65  \w     30.00  58.00   1.00    1.50    --   58.00  70.00-178.88   28
 66  \w     36.00  61.00   1.00    1.50    --   66.00  70.00 -41.68   25
 67  \w     36.00  62.00   1.00    1.50    --   66.00  71.00 -73.32   26
 68  \w     37.00  63.00   1.00    1.50    --   66.00  69.00-155.94   26
 69  \w     40.00  85.00   1.00    1.50    --   70.00  70.00  53.64   45
 70  \w     40.00  65.00   1.00    1.50    --   70.00  70.00  23.26   25
 71  \w     40.00  65.00   1.00    1.50    --   70.00  71.00-132.30   25
 72  \w     40.00  65.00   1.00    1.50    --   70.00  71.00  95.95   25
 73  \w     40.00  81.00   1.00    1.50    --   70.00  71.00-110.18   41
 74  \w     40.00  66.00   1.00    1.50    --   70.00  71.00 -29.64   26
 75  \w     40.00  90.00   1.00    1.50    --   70.00  70.00 127.75   50
 76  \w     40.00  66.00   1.00    1.50    --   70.00  71.00 -10.83   26
 77  \w     83.00 111.00   1.00    6.00    --  111.00  61.00-180.00   28
 78  \w     83.00 108.00   1.00    6.00    --  111.00  61.00 -90.00   25
 79  \w    112.00 174.00   1.00    6.00    --  111.00  61.00 -60.00   62
 80  \w     83.00 130.00   1.00    6.00    --  111.00  61.00-120.00   47
 81  \w    146.00 172.00   1.00    6.00    --  111.00  61.00 120.00   26
 82  \w    145.00 171.00   1.00    6.00    --  111.00  61.00 -90.00   26
 83  \w     83.00 108.00   1.00    6.00    --  111.00  61.00 -60.00   25
 84  \w     83.00 118.00   1.00    6.00    --  111.00  61.00 120.00   35
 85  \w    126.00 158.00   1.00    6.00    --  111.00  45.00  90.00   32
 86  \w    148.00 174.00   1.00    6.00    --  111.00  61.00  30.00   26
 87  \w     87.00 113.00   1.00    6.00    --  111.00  45.00   0.00   26
 88  \w     83.00 143.00   1.00    6.00    --  111.00  61.00  30.00   60
 89  \w     83.00 129.00   1.00    6.00    --  111.00  61.00 -30.00   46
 90  \w     43.00  69.00   1.00    6.00    --  111.00 -45.00-150.00   26
 91  \w     83.00 125.00   1.00    6.00    --  111.00  61.00  90.00   42
 92  \w    144.00 176.00   1.00    6.00    --  111.00  61.00 150.00   32
 93  \w     41.00  67.00   1.00    6.00    --  111.00 -45.00 -30.00   26
 94  \w     83.00 119.00   1.00    6.00    --  111.00  61.00 150.00   36
 95  \w     89.00 119.00   1.00    6.00    --  111.00  45.00 -60.00   30
 96  \w    128.00 154.00   1.00    6.00    --  111.00  45.00 -60.00   26
 97  \w     83.00 109.00   1.00    6.00    --  111.00  61.00-150.00   26
 98  \w     89.00 115.00   1.00    6.00    --  111.00  45.00 -30.00   26
 99  \w    140.00 172.00   1.00    6.00    --  111.00  45.00 -30.00   32
100  \w     87.00 114.00   1.00    6.00    --  111.00  45.00  90.00   27
101  \w    117.00 172.00   1.00    6.00    --  111.00  61.00  60.00   55
102  \w    138.00 174.00   1.00    6.00    --  111.00  61.00   0.00   36
103  \w     83.00 109.00   1.00    6.00    --  111.00  61.00  60.00   26
104  \w    122.00 161.00   1.00    6.00    --  111.00  61.00-180.00   39
105  \w     83.00 113.00   1.00    6.00    --  111.00  61.00   0.00   30
;
_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      0.0270058000
_diffrn_orient_matrix_UB_12      0.0966747000
_diffrn_orient_matrix_UB_13      -0.0065251000
_diffrn_orient_matrix_UB_21      -0.0171857000
_diffrn_orient_matrix_UB_22      0.0193706000
_diffrn_orient_matrix_UB_23      0.0751883000
_diffrn_orient_matrix_UB_31      0.0919259000
_diffrn_orient_matrix_UB_32      -0.0247455000
_diffrn_orient_matrix_UB_33      0.0332450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            103585
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.274
_diffrn_reflns_theta_min         3.755
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.041
_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     542
_refine_ls_number_reflns         9545
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0506P)^2^+1.2035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8233
_reflns_number_total             9545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06389a2.cif
_cod_data_source_block           101lglg24_auto
_cod_depositor_comments
'Adding full bibliography for 1573067--1573071.cif.'
_cod_database_code               1573069
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C50 H50 Zn1'
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C35-C37 \\sim C35-C37A
 with sigma of 0.02
 C36A-C35 \\sim C37A-C35 \\sim C36-C35 \\sim C37-C35
 with sigma of 0.02
3. Rigid bond restraints
 C26, C27, C28, C29, C30, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C36A \\sim C36: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C37A \\sim C37: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C36) \\sim Ueq, Uanis(C37A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C26, C27, C28, C29, C30, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H35A)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C37A)=Sof(H37D)=
 Sof(H37E)=Sof(H37F)=1-FVAR(1)
 Sof(H35)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C47(H47), C44(H44), C32(H32), C35(H35), C35(H35A)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C24(H24), C19(H19), C17(H17), C25(H25), C8(H8), C40(H40), C42(H42),
 C10(H10), C41(H41), C28(H28), C30(H30), C29(H29)
7.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C),
 C34(H34A,H34B,H34C), C45(H45A,H45B,H45C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C49(H49A,H49B,H49C), C48(H48A,H48B,H48C), C22(H22A,
 H22B,H22C), C46(H46A,H46B,H46C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C),
 C36(H36A,H36B,H36C), C36A(H36D,H36E,H36F), C37A(H37D,H37E,H37F)
;
_shelx_res_checksum              82387
_shelx_hkl_checksum              6978
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.878