Phosphine-catalyzed hydroboration of propiolonitriles: access to (<i>E</i>)-1,2-vinylcyanotrifluoroborate derivatives.
Bowen, Johnathan; Slebodnick, Carla; Santos, Webster L.; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc00603k

data_7130036
_publ_section_title
;
 Phosphine-catalyzed hydroboration of propiolonitriles: access to
 (<i>E</i>)-1,2-vinylcyanotrifluoroborate derivatives.
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc00603k
_journal_year                    2022
_chemical_formula_moiety         'C10 H8 B F3 K N O'
_chemical_formula_sum            'C10 H8 B F3 K N O'
_chemical_formula_weight         265.08
_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             2021-01-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6760(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.55436(11)
_cell_length_b                   7.90140(4)
_cell_length_c                   8.22574(5)
_cell_measurement_reflns_used    25413
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      77.7120
_cell_measurement_theta_min      4.8720
_cell_volume                     1176.545(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      99.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     25.00  51.00   0.50    0.05    --   44.00  65.00 -62.61   52
  2  \w     12.00  39.00   0.50    0.05    --   36.00  78.00 -95.53   54
  3  \w     11.00  36.00   0.50    0.05    --   36.00  79.00  17.18   50
  4  \w     31.00  87.00   0.50    0.05    --   46.62  57.00  30.00  112
  5  \w     28.00  54.00   0.50    0.05    --   48.00  69.00 128.81   52
  6  \w     33.00  76.00   0.50    0.05    --   46.62  38.00  90.00   86
  7  \w     73.00 102.00   0.50    0.25    --  110.00 -77.00 120.00   58
  8  \w     56.00  83.00   0.50    0.25    --  110.00 -77.00  90.00   54
  9  \w     41.00  66.00   0.50    0.25    --  110.00 -77.00 120.00   50
 10  \w     72.00 103.00   0.50    0.25    --  110.00 -77.00   0.00   62
 11  \w     44.00  70.00   0.50    0.25    --  110.00 -77.00 -90.00   52
 12  \w     65.00  93.00   0.50    0.25    --  110.00 -77.00-120.00   56
 13  \w     48.00  82.00   0.50    0.25    --  110.00 -77.00-180.00   68
 14  \w     39.00  68.00   0.50    0.25    --  110.00 -61.00-150.00   58
 15  \w     40.00  93.00   0.50    0.25    --  110.00 -77.00-150.00  106
 16  \w     39.00  69.00   0.50    0.25    --  110.00 -61.00-120.00   60
 17  \w    -25.00  41.00   0.50    0.05    --   46.62 -38.00-120.00  132
 18  \w     38.00  68.00   0.50    0.25    --  110.00 -77.00   0.00   60
 19  \w     39.00  65.00   0.50    0.25    --  110.00 -61.00  90.00   52
 20  \w    111.00 141.00   0.50    0.25    --  110.00  30.00  90.00   60
 21  \w    130.00 178.00   0.50    0.25    --  110.00  77.00  90.00   96
 22  \w     86.00 165.00   0.50    0.25    --  110.00  77.00  60.00  158
 23  \w     86.00 112.00   0.50    0.25    --  110.00  77.00  90.00   52
 24  \w     87.00 113.00   0.50    0.25    --  110.00  77.00  30.00   52
 25  \w     86.00 114.00   0.50    0.25    --  110.00  77.00 -30.00   56
 26  \w    130.00 156.00   0.50    0.25    --  110.00  77.00 -30.00   52
 27  \w    124.00 178.00   0.50    0.25    --  110.00  77.00 -60.00  108
 28  \w     86.00 114.00   0.50    0.25    --  110.00  77.00-180.00   56
 29  \w     88.00 134.00   0.50    0.25    --  110.00  77.00-150.00   92
 30  \w    121.00 147.00   0.50    0.25    --  110.00  77.00-120.00   52
 31  \w     88.00 115.00   0.50    0.25    --  110.00  77.00-120.00   54
 32  \w     86.00 112.00   0.50    0.25    --  110.00  77.00 -60.00   52
 33  \w    153.00 178.00   0.50    0.25    --  110.00  77.00 -90.00   50
 34  \w    138.00 176.00   0.50    0.25    --  110.00  77.00   0.00   76
 35  \w     86.00 130.00   0.50    0.25    --  110.00  77.00 150.00   88
 36  \w    136.00 175.00   0.50    0.25    --  110.00  77.00 150.00   78
 37  \w     39.00  84.00   0.50    0.05    --   60.00  70.00 137.74   90
 38  \w     86.00 112.00   0.50    0.25    --  110.00  77.00   0.00   52
 39  \w     83.00 114.00   0.50    0.25    --  104.00  75.00 -99.32   62
 40  \w     87.00 141.00   0.50    0.25    --  110.00  77.00 -90.00  108
 41  \w    144.00 178.00   0.50    0.25    --  110.00  77.00-180.00   68
 42  \w     34.00  70.00   0.50    0.05    --   52.00  68.00-179.06   72
 43  \w     37.00  63.00   0.50    0.05    --   56.00  69.00-131.06   52
 44  \w     36.00  67.00   0.50    0.05    --   56.00  69.00 -68.91   62
 45  \w     36.00  62.00   0.50    0.05    --   56.00  67.00  22.04   52
 46  \w     42.00  70.00   0.50    0.05    --   60.00  65.00  80.02   56
 47  \w     94.00 146.00   0.50    0.25    --  110.00  61.00 120.00  104
 48  \w     95.00 145.00   0.50    0.25    --  110.00  61.00  30.00  100
 49  \w    130.00 168.00   0.50    0.25    --  110.00  61.00 -30.00   76
 50  \w    145.00 170.00   0.50    0.25    --  110.00  61.00 -60.00   50
 51  \w     93.00 119.00   0.50    0.25    --  110.00  61.00-150.00   52
 52  \w    125.00 166.00   0.50    0.25    --  110.00  61.00-150.00   82
 53  \w    149.00 176.00   0.50    0.25    --  110.00  61.00-120.00   54
 54  \w     97.00 143.00   0.50    0.25    --  110.00  61.00-120.00   92
 55  \w     93.00 126.00   0.50    0.25    --  110.00  61.00 -60.00   66
 56  \w     94.00 125.00   0.50    0.25    --  110.00  61.00 -30.00   62
 57  \w    153.00 178.00   0.50    0.25    --  110.00  61.00  30.00   50
 58  \w     95.00 169.00   0.50    0.25    --  110.00  61.00 150.00  148
 59  \w    132.00 163.00   0.50    0.25    --  110.00  45.00 150.00   62
 60  \w     94.00 161.00   0.50    0.25    --  110.00  61.00  60.00  134
 61  \w     96.00 126.00   0.50    0.25    --  110.00  45.00 150.00   60
 62  \w     93.00 141.00   0.50    0.25    --  110.00  61.00   0.00   96
 63  \w    147.00 175.00   0.50    0.25    --  110.00  61.00   0.00   56
 64  \w    149.00 175.00   0.50    0.25    --  110.00  45.00  30.00   52
 65  \w     96.00 156.00   0.50    0.25    --  110.00  45.00 120.00  120
 66  \w    130.00 156.00   0.50    0.25    --  110.00  45.00 -30.00   52
 67  \w     96.00 124.00   0.50    0.25    --  110.00  45.00 -30.00   56
 68  \w    104.00 144.00   0.50    0.25    --  110.00  45.00  30.00   80
 69  \w    142.00 168.00   0.50    0.25    --  110.00  30.00  90.00   52
 70  \w    105.00 177.00   0.50    0.25    --  110.00  45.00 -90.00  144
 71  \w     95.00 135.00   0.50    0.25    --  110.00  61.00-180.00   80
 72  \w    124.00 150.00   0.50    0.25    --  110.00 127.00-156.27   52
 73  \w     97.00 139.00   0.50    0.25    --  110.00 125.00   0.00   84
 74  \w    148.00 178.00   0.50    0.25    --  110.00 125.00   0.00   60
 75  \w    111.00 158.00   0.50    0.25    --  110.00 125.00  60.00   94
 76  \w     95.00 148.00   0.50    0.25    --  110.00 125.00 150.00  106
 77  \w    133.00 168.00   0.50    0.25    --  110.00 109.00 105.00   70
 78  \w     39.00  66.00   0.50    0.25    --  110.00 -94.00   0.00   54
 79  \w     34.00  95.50   0.50    0.05    --   46.62-125.00  90.00  123
 80  \w     86.00 112.00   0.50    0.25    --  110.00-125.00-120.00   52
 81  \w     82.00 112.00   0.50    0.25    --  110.00-125.00-180.00   60
 82  \w     50.00  79.00   0.50    0.25    --  110.00-125.00-180.00   58
 83  \w     38.00  67.00   0.50    0.25    --  110.00-125.00-120.00   58
 84  \w     79.00 112.00   0.50    0.25    --  110.00-125.00 -90.00   66
 85  \w     77.00 112.00   0.50    0.25    --  110.00-125.00 -30.00   70
 86  \w     63.00 112.00   0.50    0.25    --  110.00-125.00   0.00   98
 87  \w     81.00 108.00   0.50    0.25    --  110.00-109.00  10.00   54
 88  \w     39.00  88.00   0.50    0.25    --  110.00 -94.00 -30.00   98
 89  \w     77.00 112.00   0.50    0.25    --  110.00-125.00 120.00   70
 90  \w     39.00  75.00   0.50    0.25    --  110.00-125.00 120.00   72
 91  \w     40.00  75.00   0.50    0.25    --  110.00 -94.00  90.00   70
 92  \w     78.00 106.00   0.50    0.25    --  110.00 -94.00  90.00   56
 93  \w     22.00  57.00   0.50    0.05    --   46.62-109.00  10.00   70
 94  \w     81.00 106.00   0.50    0.25    --  110.00 -94.00-180.00   50
 95  \w     46.00  72.00   0.50    0.25    --  110.00 -94.00-180.00   52
 96  \w     72.00 100.00   0.50    0.25    --  110.00 -94.00   0.00   56
 97  \w     38.00  70.00   0.50    0.25    --  110.00 -94.00  60.00   64
 98  \w      4.00  29.00   0.50    0.05    --   32.00  86.00-122.30   50
 99  \w    -59.00 -32.00   0.50    0.05    --   16.00 166.00 -71.53   54
100  \w    -71.00 -15.00   0.50    0.25    --  -88.50  61.00  60.00  112
101  \w    -74.00 -49.00   0.50    0.25    --  -88.50 109.00 105.00   50
102  \w    -82.00  -9.00   0.50    0.05    --  -46.62 109.00 105.00  146
103  \w     -1.00  27.00   0.50    0.05    --   28.00  89.00 129.53   56
104  \w    -28.00  27.00   0.50    0.05    --  -46.62  19.00-150.00  110
105  \w   -118.00 -72.00   0.50    0.05    --  -46.62 -19.00 -90.00   92
106  \w   -101.00 -70.00   0.50    0.25    --  -88.50 -69.00-139.23   62
107  \w    -65.00 -39.00   0.50    0.05    --  -60.00 -69.00-118.57   52
108  \w    -65.00 -39.00   0.50    0.05    --  -56.00 -70.00 -66.20   52
109  \w    -78.00 -52.00   0.50    0.25    --  -72.00 -68.00 -60.76   52
110  \w   -150.00-124.00   0.50    0.25    --  -88.50 -69.00-139.23   52
111  \w    -95.00 -69.00   0.50    0.25    --  -88.50 -68.00 -70.21   52
112  \w    -93.00 -68.00   0.50    0.25    --  -88.50 -68.00  -7.60   50
113  \w    -63.00 -37.00   0.50    0.05    --  -56.00 -70.00  -0.85   52
114  \w    -81.00 -45.00   0.50    0.05    --  -64.00 -68.00  48.35   72
115  \w   -100.00 -68.00   0.50    0.25    --  -88.50 -69.00 128.95   64
116  \w    -76.00 -40.00   0.50    0.05    --  -60.00 -67.00 158.31   72
117  \w   -131.00 -97.00   0.50    0.05    --  -60.00 -67.00 158.31   68
118  \w    -80.00 -69.50   0.50    0.25    --  -68.00 -67.00 142.16   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0439884000
_diffrn_orient_matrix_UB_12      0.1618411000
_diffrn_orient_matrix_UB_13      -0.0610149000
_diffrn_orient_matrix_UB_21      -0.0704318000
_diffrn_orient_matrix_UB_22      -0.0823382000
_diffrn_orient_matrix_UB_23      0.0342730000
_diffrn_orient_matrix_UB_31      0.0185357000
_diffrn_orient_matrix_UB_32      0.0710356000
_diffrn_orient_matrix_UB_33      0.1787913000
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32096
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.077
_diffrn_reflns_theta_min         2.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.187
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'crystallized from CH3CN / Et2O'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0328P)^2^+0.5392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             2515
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00603k2.cif
_cod_data_source_block           cs2643
_cod_database_code               7130036
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H8 B F3 K N O'
_chemical_oxdiff_usercomment     'Johnathan Bowen/Santos (JMB-05-071)'
_shelx_estimated_absorpt_t_max   0.758
_shelx_estimated_absorpt_t_min   0.473
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              65179
_olex2_date_sample_submission    2021-01-12
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop with Krytox oil'
_olex2_submission_original_sample_id JMB-05-071
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.715
_oxdiff_exptl_absorpt_empirical_full_min 0.584