Catalytic, Enantioselective Synthesis of Allenyl Boronates.
Gao, De-Wei; Xiao, Yiyang; Liu, Mingyu; Liu, Zhen; Karunananda, Malkanthi K.; Chen, Jason S.; Engle, Keary M.; ACS catalysis 8 (2018) 3650–3654; doi:10.1021/acscatal.8b00626

data_4515629
_publ_section_title
;
 Catalytic, Enantioselective Synthesis of Allenyl Boronates.
;
_journal_issue                   4
_journal_name_full               'ACS catalysis'
_journal_page_first              3650
_journal_page_last               3654
_journal_paper_doi               10.1021/acscatal.8b00626
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.25(C52 H60 B4 F12 K4)'
_chemical_formula_sum            'C13 H15 B F3 K'
_chemical_formula_weight         278.16
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                72.6270(10)
_cell_angle_beta                 75.8460(10)
_cell_angle_gamma                89.9760(10)
_cell_formula_units_Z            4
_cell_length_a                   9.0823(6)
_cell_length_b                   10.0446(6)
_cell_length_c                   16.7815(11)
_cell_measurement_reflns_used    6050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.32
_cell_volume                     1412.38(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15714
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.148
_diffrn_reflns_theta_min         2.131
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.493
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0493 before and 0.0426 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0478 before and 0.0410 after correction.
 The Ratio of minimum to maximum transmission is 0.89.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 30674 reflections, Rint = 0.0293
 (22342 with I > 3sig(I), Rint = 0.0274)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.009(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         15714
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0399P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                14505
_reflns_number_total             15714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b00626_si_003.cif
_cod_data_source_block           engle80
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515629
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.870
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4407(6)
 0.5593(6)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C105(H10D,H10E), C106(H10F,H10G),
 C107(H10H,H10I), C205(H20D,H20E), C206(H20F,H20G), C207(H20H,H20I), C305(H30D,
 H30E), C306(H30F,H30G), C307(H30H,H30I)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C102(H102),
 C109(H109), C110(H110), C111(H111), C112(H112), C113(H113), C202(H202),
 C209(H209), C210(H210), C211(H211), C212(H212), C213(H213), C302(H302),
 C309(H309), C310(H310), C311(H311), C312(H312), C313(H313)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C101(H10A,H10B,H10C), C201(H20A,H20B,H20C), C301(H30A,H30B,
 H30C)
;
_shelx_res_checksum              28926
_shelx_hkl_checksum              22778
_olex2_submission_special_instructions 'No special instructions were received'