Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation and Crotylation of Aldehydes.
Yuan, Jinping; Jain, Pankaj; Antilla, Jon C.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01646

data_4038848
_publ_section_title
;
 Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral
 Phosphoric Acid-Catalyzed Allylation, Propargylation and Crotylation of
 Aldehydes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01646
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 N2 O6'
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.92100(10)
_cell_length_b                   9.65970(10)
_cell_length_c                   32.1824(5)
_cell_measurement_reflns_used    9205
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      73.6040
_cell_measurement_theta_min      2.7210
_cell_volume                     1840.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      0.00  83.00   0.50    0.10    --   45.87-103.00-130.00  166
  2  \w   -119.00 -27.00   0.50    0.40    -- -100.00  65.00-116.00  184
  3  \w   -173.00 -83.00   0.50    0.40    -- -100.00-103.00-130.00  180
  4  \w     84.00 175.00   0.50    0.40    --  101.75  61.00  96.00  182
  5  \w   -119.00 -73.00   0.50    0.10    --  -45.87-125.00 -60.00   92
  6  \w   -119.00 -73.00   0.50    0.10    --  -45.87-125.00-120.00   92
  7  \w   -119.00 -73.00   0.50    0.10    --  -45.87-125.00 -90.00   92
  8  \w     20.00  95.00   0.50    0.10    --   45.87-125.00-180.00  150
  9  \w   -114.00 -27.00   0.50    0.40    -- -100.00  45.00   0.00  174
 10  \w   -173.00 -78.00   0.50    0.40    -- -100.00 -94.00-180.00  190
 11  \w   -117.00 -27.00   0.50    0.40    -- -100.00 125.00  90.00  180
 12  \w     29.00 109.00   0.50    0.40    --  101.75 -94.00-120.00  160
 13  \w   -119.00 -28.00   0.50    0.10    --  -45.87 -61.00 -42.00  182
 14  \w   -119.00 -30.00   0.50    0.10    --  -45.87 -57.00-150.00  178
 15  \w     29.00 119.00   0.50    0.10    --   45.87  61.00  96.00  180
 16  \w   -175.00-130.00   0.50    0.40    -- -100.00 -30.00  30.00   90
 17  \w   -173.00 -82.00   0.50    0.40    -- -100.00 -61.00 -90.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438279000
_diffrn_orient_matrix_UB_12      0.1012907000
_diffrn_orient_matrix_UB_13      -0.0360848000
_diffrn_orient_matrix_UB_21      0.2453901000
_diffrn_orient_matrix_UB_22      0.0520745000
_diffrn_orient_matrix_UB_23      0.0030641000
_diffrn_orient_matrix_UB_31      0.0745614000
_diffrn_orient_matrix_UB_32      -0.1115864000
_diffrn_orient_matrix_UB_33      -0.0313218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17029
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         2.746
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0476P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                3232
_reflns_number_total             3598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01646_si_002.cif
_cod_data_source_block           yjp_frxl
_cod_database_code               4038848
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C18(H18), C7(H7), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C13(H13), C15(H15), C9(H9)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              69562
_shelx_hkl_checksum              6644
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.548
_oxdiff_exptl_absorpt_empirical_full_min 0.736