Efficient enantioselective synthesis of dihydropyrans using a chiral n,n'-dioxide as organocatalyst.
Feng, Juhua; Fu, Xuan; Chen, Zhenling; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; Organic letters 15 (2013) 2640–2643; doi:10.1021/ol400894j

data_1512053
_publ_section_title
;
 Efficient enantioselective synthesis of dihydropyrans using a chiral
 n,n'-dioxide as organocatalyst.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2640
_journal_page_last               2643
_journal_paper_doi               10.1021/ol400894j
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H50 N4 O4, H2 O'
_chemical_formula_sum            'C36 H52 N4 O5'
_chemical_formula_weight         620.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-14
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 131.651(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.4401(18)
_cell_length_b                   22.3692(9)
_cell_length_c                   18.4184(14)
_cell_measurement_reflns_used    4851
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      29.1057
_cell_measurement_theta_min      2.9141
_cell_volume                     8139.7(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -36.00    2.40   0.8000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924  -37.0000 -150.0000 48

  2 omega  -22.00    5.20   0.8000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924  -99.0000   60.0000 34

  3 omega   46.00   90.00   0.8000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611  178.0000   90.0000 55

  4 omega  -50.00   71.60   0.8000   27.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611    0.0000 -180.0000 152
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0042860000
_diffrn_orient_matrix_UB_12      0.0197474000
_diffrn_orient_matrix_UB_13      -0.0257089000
_diffrn_orient_matrix_UB_21      0.0220794000
_diffrn_orient_matrix_UB_22      0.0178783000
_diffrn_orient_matrix_UB_23      0.0422763000
_diffrn_orient_matrix_UB_31      0.0279763000
_diffrn_orient_matrix_UB_32      -0.0171665000
_diffrn_orient_matrix_UB_33      0.0145491000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18378
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.013
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         13153
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.1136
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3001
_refine_ls_wR_factor_ref         0.3260
_reflns_number_gt                8986
_reflns_number_total             13153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400894j_si_002.cif
_cod_data_source_block           121225_s4_fjh
_cod_database_code               1512053
_chemical_oxdiff_formula         C12H14N2O3
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32