The Evans Aldol-Prins cyclization: a general and stereoselective method for the synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans.
Álvarez-Méndez, Sergio J; García, Celina; Martín, Víctor S; Chemical communications (Cambridge, England) 52 (2016) 3380–3383; doi:10.1039/c6cc00160b

data_7118624
_publ_section_title
;
 The Evans Aldol-Prins cyclization: a general and stereoselective method
 for the synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3380
_journal_page_last               3383
_journal_paper_doi               10.1039/c6cc00160b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C19 H33 N O5'
_chemical_formula_sum            'C19 H33 N O5'
_chemical_formula_weight         355.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-12-16
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2015-12-16 deposited with the CCDC.
2016-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.138(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4474(11)
_cell_length_b                   10.8872(5)
_cell_length_c                   9.4942(5)
_cell_measurement_reflns_used    3369
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.5280
_cell_measurement_theta_min      4.5440
_cell_volume                     1984.67(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w     24.00  78.00   1.00    1.50    --   41.36 -99.00  30.00   54
  2  \w     50.00  98.00   1.00   10.00    --  106.58 -45.00  60.00   48
  3  \w     42.00  87.00   1.00   10.00    --  106.58 -30.00 -30.00   45
  4  \w     78.00 121.00   1.00   10.00    --  106.58  30.00 -90.00   43
  5  \w    141.00 171.00   1.00   10.00    --  106.58  30.00 -90.00   30
  6  \w     94.00 171.00   1.00   10.00    --  106.58 125.00-150.00   77
  7  \w     77.00 139.00   1.00   10.00    --  106.58  61.00-180.00   62
  8  \w     39.00  91.00   1.00   10.00    --  106.58 -30.00-150.00   52
  9  \w     53.00 105.00   1.00   10.00    --  106.58 -94.00-150.00   52
 10  \w     31.00  79.00   1.00   10.00    --  106.58 -30.00 -90.00   48
 11  \w    -32.00  29.00   1.00    1.50    --  -41.36  38.00 150.00   61
 12  \w    -99.00 -14.00   1.00    1.50    --  -41.36 -57.00-150.00   85
 13  \w   -105.00 -73.00   1.00    1.50    --  -41.36-135.00 174.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0710966000
_diffrn_orient_matrix_UB_12      -0.0518135000
_diffrn_orient_matrix_UB_13      0.0228420000
_diffrn_orient_matrix_UB_21      -0.0372476000
_diffrn_orient_matrix_UB_22      0.0983200000
_diffrn_orient_matrix_UB_23      -0.1014401000
_diffrn_orient_matrix_UB_31      0.0004766000
_diffrn_orient_matrix_UB_32      -0.0875704000
_diffrn_orient_matrix_UB_33      -0.1272225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7912
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.607
_diffrn_reflns_theta_min         4.606
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0895
_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^)+(0.1210P)^2^+1.8550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.2303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3250
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00160b2.cif
_cod_data_source_block           sam552e1
_cod_depositor_comments          'Adding full bibliography for 7118624.cif.'
_cod_database_code               7118624
_chemical_oxdiff_formula         C19H33NO5
_reflns_odcompleteness_completeness 99.33
_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, All O(H) groups
2. Others
 Sof(H11A)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C13B)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(H11)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C12A)=Sof(H12A)=
 Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(H6A)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(2)
 Sof(H6B)=Sof(C18B)=Sof(H18A)=Sof(H18B)=Sof(C19B)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C7(H7), C5(H5), C15(H15), C6(H6B), C6(H6A), C11(H11),
 C11(H11A)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C18B(H18A,H18B),
 C18A(H18C,H18D)
3.c Me refined with riding coordinates:
 C12B(H12D,H12E,H12F)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C13A(H13A,H13B,H13C), C12A(H12A,
 H12B,H12C), C13B(H13D,H13E,H13F), C19B(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              85269
_shelx_hkl_checksum              60115
_shelx_shelxl_version_number     2014/7
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.790