One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives.
Pujol, Alba; Calow, Adam D. J.; Batsanov, Andrei S.; Whiting, Andrew; Organic & biomolecular chemistry 13 (2015) 5122–5130; doi:10.1039/c4ob02657h

data_7154383
_publ_section_title
;
 One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived
 imines; functionalisation to homoallylic boronate carboxylate ester
 derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5122
_journal_page_last               5130
_journal_paper_doi               10.1039/c4ob02657h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C22 H18 Cl N'
_chemical_formula_sum            'C22 H18 Cl N'
_chemical_formula_weight         331.82
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/cc13xm3r
_audit_creation_date             2014-10-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.30 svn.r3070 for OlexSys, GUI svn.r4932)
;
_audit_update_record
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                89.497(4)
_cell_angle_beta                 79.611(4)
_cell_angle_gamma                78.354(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6806(5)
_cell_length_b                   12.4099(9)
_cell_length_c                   12.5191(9)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    120
_cell_measurement_theta_max      73.52
_cell_measurement_theta_min      3.59
_cell_volume                     849.85(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.902
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5801
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.674
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_correction_T_min  0.5673
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1563 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.5278.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.705
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1550P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2033
_refine_ls_wR_factor_ref         0.2178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2399
_reflns_number_total             3006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02657h2.cif
_cod_data_source_block           2e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 

 Adding full bibliography for 7154381--7154385.cif.
;
_cod_database_code               7154383
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.336
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C3(H3), C12(H12), C16(H16), C7(H7), C4(H4), C19(H19),
 C9(H9), C6(H6), C13(H13), C20(H20), C22(H22), C14(H14), C18(H18), C15(H15),
 C21(H21)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'