Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones.
Fernandes, Alessandra A. G.; Leonarczyk, Ives A.; Ferreira, Marco A. B.; Dias, Luiz Carlos; Organic & biomolecular chemistry 17 (2019) 3167–3180; doi:10.1039/c9ob00358d

data_7156700
_publ_section_title
;
 Diastereoselectivity in the boron aldol reaction of \a-alkoxy and
 \a,\b-bis-alkoxy methyl ketones.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3167
_journal_page_last               3180
_journal_paper_doi               10.1039/c9ob00358d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H43 N O6 Si2'
_chemical_formula_sum            'C24 H43 N O6 Si2'
_chemical_formula_weight         497.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-20 deposited with the CCDC.    2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3010(10)
_cell_length_b                   8.1121(4)
_cell_length_c                   34.9928(17)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.945
_cell_measurement_theta_min      4.535
_cell_volume                     5762.7(5)
_computing_cell_refinement       'SAINT v8.34A (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, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'BRUKER APEX CCD DETECTOR DIFRACTION'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            25191
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.709
_diffrn_reflns_theta_min         2.525
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.8022.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       needle
_exptl_crystal_F_000             2160
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.049
_refine_diff_density_max         1.919
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 3222 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         9505
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1194P)^2^+2.6940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.1922
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.829
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                8196
_reflns_number_total             9505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00358d2.cif
_cod_data_source_block           aagf-311_a
_cod_depositor_comments
'Adding full bibliography for 7156698--7156700.cif.'
_cod_database_code               7156700
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.701
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00H), C00N(H00N), C00P(H00P), C00R(H00R), C019(H019), C01G(H4AA)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C01A(H2AA,HF)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C00Q(H00Q), C00U(H00U), C00W(H00W), C00Z(H00Z), C014(H014),
 C016(H016), C01N(H6AA)
2.d Idealised Me refined as rotating group:
 C00M(H00E,H00F,H00G), C00Y(H00A,H00B,H00C), C010(H01,H,HA), C011(H01A,H01B,
 H01C), C017(H0AA,HB,HC), C018(H1AA,HD,HE), C01B(H3AA,HG,HH), C01D(H01D,H01E,
 H01F), C01E(H01G,H01H,H01I), C01F(H01J,H01K,H01L), C01H(H01M,H01N,H01O),
 C01I(H01P,H01Q,H01R), C01J(H5AA,HI,HJ), C01K(H01S,H01T,H01U), C01M(H01V,H01W,
 H01X), C01O(H7AA,HK,HL), C01P(H01Y,HM,HN), C01Q(H01Z,HO,HP), C01R(H8AA,HQ,HR),
 C01S(H9AA,HS,HT), C01T(H0BA,HU,HV), C01U(H1BA,HW,HX)
2.e Idealised tetrahedral OH refined as rotating group:
 O008(H008), O00C(H00D)
;
_shelx_res_checksum              53457
_shelx_fab_checksum              33501
_olex2_submission_special_instructions 'No special instructions were received'