Borylative cyclisation of diynes using BCl<sub>3</sub> and borocations.
Warner, Andrew J.; Enright, Kieron M.; Cole, John M.; Yuan, Kang; McGough, John S.; Ingleson, Michael J.; Organic & biomolecular chemistry 17 (2019) 5520–5525; doi:10.1039/c9ob00991d

data_7156872
_publ_section_title
;
 Borylative cyclisation of diynes using BCl<sub>3</sub> and borocations.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5520
_journal_page_last               5525
_journal_paper_doi               10.1039/c9ob00991d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C28 H21 B F4 O2'
_chemical_formula_sum            'C28 H21 B F4 O2'
_chemical_formula_weight         476.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
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Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
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2017-01-26 deposited with the CCDC.    2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                74.768(7)
_cell_angle_beta                 73.263(6)
_cell_angle_gamma                72.295(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1811(5)
_cell_length_b                   12.0413(9)
_cell_length_c                   12.5311(10)
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      26.6290
_cell_measurement_theta_min      3.7470
_cell_volume                     1105.21(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      150.02(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8370
_diffrn_measurement_details
;
  1 omega    3.00   83.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601   57.0000  -60.0000 80

  2 omega  -12.00   45.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601   80.0000   21.0000 57

  3 omega  -40.00   36.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -57.0000   60.0000 76

  4 omega  -54.00   55.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -19.0000  120.0000 109

  5 omega   18.00   59.00   1.0000    3.4400
omega____ theta____ kappa____ phi______ frames
    -       18.8601  -99.0000 -180.0000 41
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_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
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_diffrn_orient_matrix_UB_12      -0.0537585000
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_diffrn_orient_matrix_UB_21      -0.0226020000
_diffrn_orient_matrix_UB_22      -0.0301560000
_diffrn_orient_matrix_UB_23      -0.0331613000
_diffrn_orient_matrix_UB_31      0.0888195000
_diffrn_orient_matrix_UB_32      -0.0130568000
_diffrn_orient_matrix_UB_33      -0.0309007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8344
_diffrn_reflns_theta_full        29.2123
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4311
_exptl_crystal_description       plate
_exptl_crystal_F_000             492.3293
_exptl_crystal_recrystallization_method
'Slow evaporation of a solution in toluene'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.4045
_refine_diff_density_min         -0.4577
_refine_diff_density_rms         0.1071
_refine_ls_d_res_high            0.7281
_refine_ls_d_res_low             5.8885
_refine_ls_goodness_of_fit_ref   1.0502
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0502
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.6160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3160
_reflns_number_total             4969
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00991d2.cif
_cod_data_source_block           amji373
_cod_depositor_comments
'Adding full bibliography for 7156872--7156873.cif.'
_cod_database_code               7156872
_chemical_oxdiff_formula         C28H21BF4O2
_chemical_oxdiff_usercomment     'AJW f5-dibenzopentalene(Ph)(BPin)'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C39(H39), C15(H15), C36(H36), C23(H23), C29(H29), C42(H42), C50(H50),
 C45(H45), C12(H12)
2.b Idealised Me refined as rotating group:
 C48(H48a,H48b,H48c), C51(H51a,H51b,H51c), C52(H52a,H52b,H52c), C53(H53a,H53b,
 H53c)
;
_olex2_exptl_crystal_mounting_method
'Mounted in a Oxford cryosystems cold stream at 150 K'
_olex2_submission_special_instructions 'No special instructions were received'