Functionalized geminal-diborylalkanes from various electron-deficient alkynes and B2pin2
Gao, Guoliang; Kuang, Zhijie; Song, Qiuling; Organic Chemistry Frontiers 5 (2018) 2249–; doi:10.1039/C8QO00513C

data_1554359
_publ_section_title
;
 Functionalized geminal-diborylalkanes from various electron-deficient
 alkynes and B2pin2
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2249
_journal_paper_doi               10.1039/C8QO00513C
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C21 H31 B2 N O4'
_chemical_formula_sum            'C21 H31 B2 N O4'
_chemical_formula_weight         383.09
_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     direct
_audit_creation_date             2016-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-12-20 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                70.045(10)
_cell_angle_beta                 86.183(8)
_cell_angle_gamma                84.832(8)
_cell_formula_units_Z            2
_cell_length_a                   9.6906(9)
_cell_length_b                   10.9669(11)
_cell_length_c                   11.5436(13)
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    295.1(2)
_cell_measurement_theta_max      26.2330
_cell_measurement_theta_min      3.1940
_cell_volume                     1147.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0329730000
_diffrn_orient_matrix_UB_12      -0.0031371000
_diffrn_orient_matrix_UB_13      0.0540922000
_diffrn_orient_matrix_UB_21      0.0653069000
_diffrn_orient_matrix_UB_22      0.0039577000
_diffrn_orient_matrix_UB_23      -0.0321901000
_diffrn_orient_matrix_UB_31      -0.0075497000
_diffrn_orient_matrix_UB_32      0.0688010000
_diffrn_orient_matrix_UB_33      -0.0178140000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.172
_diffrn_reflns_theta_min         2.880
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       grism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0724
_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^)+(0.0781P)^2^+0.3922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.2056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2923
_reflns_number_total             5241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00513c2.cif
_cod_data_source_block           exp_3036
_cod_database_code               1554359
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.695