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_7156873
_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         'C30 H30 B Cl O4'
_chemical_formula_sum            'C30 H30 B Cl O4'
_chemical_formula_weight         500.85
_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
_audit_creation_date             2017-01-25
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Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
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_audit_update_record
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2017-01-26 deposited with the CCDC.    2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                72.871(7)
_cell_angle_beta                 85.108(6)
_cell_angle_gamma                75.762(7)
_cell_formula_units_Z            2
_cell_length_a                   9.8844(8)
_cell_length_b                   11.0536(8)
_cell_length_c                   12.8011(9)
_cell_measurement_reflns_used    3601
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      27.4660
_cell_measurement_theta_min      3.9180
_cell_volume                     1295.41(18)
_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)
(compiled Dec  3 2012,18:21:49)
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_computing_data_reduction
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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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8413
_diffrn_measurement_details
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  1 omega   -2.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       20.2703   57.0000  -30.0000 36

  2 omega  -12.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       20.2703   37.0000 -120.0000 105

  3 omega   -4.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -99.0000   60.0000 30

  4 omega  -43.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766   57.0000   90.0000 92

  5 omega    9.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766   37.0000  150.0000 26

  6 omega  -89.00    5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -57.0000  -60.0000 94

  7 omega  -18.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.1766  -99.0000 -180.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0374179000
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_diffrn_orient_matrix_UB_13      0.0258677000
_diffrn_orient_matrix_UB_21      0.0234051000
_diffrn_orient_matrix_UB_22      -0.0087233000
_diffrn_orient_matrix_UB_23      -0.0518038000
_diffrn_orient_matrix_UB_31      0.0594489000
_diffrn_orient_matrix_UB_32      0.0238867000
_diffrn_orient_matrix_UB_33      0.0031133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9932
_diffrn_reflns_theta_full        28.4281
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         3.23
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72440
_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            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.2839
_exptl_crystal_description       block
_exptl_crystal_F_000             528.5437
_exptl_crystal_recrystallization_method 'Slow evaporation of DCM solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3517
_refine_diff_density_min         -0.3809
_refine_diff_density_rms         0.0749
_refine_ls_d_res_high            0.7465
_refine_ls_d_res_low             6.3144
_refine_ls_goodness_of_fit_ref   1.0457
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0457
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0530P)^2^+0.3430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3925
_reflns_number_total             5488
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00991d2.cif
_cod_data_source_block           amji333
_cod_depositor_comments
'Adding full bibliography for 7156872--7156873.cif.'
_cod_original_cell_volume        1295.40(18)
_cod_database_code               7156873
_chemical_oxdiff_formula         'B Cl O4 C30 H30'
_chemical_oxdiff_usercomment     'Andy dichloro cyclisation'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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:
 C29(H29), C12(H12), C22(H22), C26(H26), C25(H25), C21(H21), C11(H11),
 C10(H10), C28(H28), C19(H19), C9(H9), C18(H18)
2.b Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C30(H30a,H30b,H30c), C6(H6a,H6b,H6c), C2(H2a,H2b,H2c),
 C5(H5a,H5b,H5c), C1(H1a,H1b,H1c)
;
_olex2_exptl_crystal_mounting_method
'Mounted in a Oxford Cryostystems cryo probe at 150 K'
_olex2_submission_special_instructions 'No special instructions were received'