Asymmetric Organocatalytic Reductive Coupling Reactions between Benzylidene Pyruvates and Aldehydes.
Horwitz, Matthew A.; Zavesky, Blane P.; Martinez-Alvarado, Jesus I; Johnson, Jeffrey S.; Organic letters 18 (2016) 36–39; doi:10.1021/acs.orglett.5b03127

data_1542393
_publ_section_title
;
 Asymmetric Organocatalytic Reductive Coupling Reactions between
 Benzylidene Pyruvates and Aldehydes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              36
_journal_page_last               39
_journal_paper_doi               10.1021/acs.orglett.5b03127
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 Br O7 P'
_chemical_formula_sum            'C20 H22 Br O7 P'
_chemical_formula_weight         485.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.492(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5750(4)
_cell_length_b                   7.9619(5)
_cell_length_c                   23.2886(15)
_cell_measurement_reflns_used    9065
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      3.80
_cell_volume                     1033.69(12)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18573
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.139
_diffrn_reflns_theta_min         1.897
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.796
_exptl_absorpt_correction_T_max  0.7774
_exptl_absorpt_correction_T_min  0.5725
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.7364.
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    1.559
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0338P)^2^+1.7076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3838
_reflns_number_total             4022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03127_si_001.cif
_cod_data_source_block           x1509010
_cod_database_code               1542393
_shelx_estimated_absorpt_t_max   0.700
_shelx_estimated_absorpt_t_min   0.556
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.94(3) 0.06(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C22(H22), C23(H23), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C21(H21A,H21B,H21C)
3.d Idealised tetrahedral OH refined as rotating group:
 O17(H17)
;
_shelx_res_checksum              73999
_shelx_hkl_checksum              36298
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'