Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction.
Mondal, Pravat; Argade, Narshinha P.; Organic & biomolecular chemistry 14 (2016) 10394–10406; doi:10.1039/c6ob01438k

data_7155291
_publ_section_title
;
 Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol
 and (-)-3-epitacamonine: observation of a substrate dependent
 diastereoselectivity reversal of an aldol reaction.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10394
_journal_page_last               10406
_journal_paper_doi               10.1039/c6ob01438k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 N2 O5 S'
_chemical_formula_sum            'C25 H28 N2 O5 S'
_chemical_formula_weight         468.55
_chemical_name_systematic        'Amine Ester'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2015-09-13 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0934(4)
_cell_length_b                   10.9932(4)
_cell_length_c                   25.0614(14)
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.9340
_cell_measurement_theta_min      3.7440
_cell_volume                     2505.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1640
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.8115
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0723784000
_diffrn_orient_matrix_UB_12      -0.0216551000
_diffrn_orient_matrix_UB_13      0.0046306000
_diffrn_orient_matrix_UB_21      0.0069360000
_diffrn_orient_matrix_UB_22      -0.0144900000
_diffrn_orient_matrix_UB_23      -0.0274928000
_diffrn_orient_matrix_UB_31      0.0282825000
_diffrn_orient_matrix_UB_32      0.0590012000
_diffrn_orient_matrix_UB_33      -0.0050244000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8665
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                4564
_reflns_number_total             6669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01438k2.cif
_cod_data_source_block           pravateur
_cod_depositor_comments
'Adding full bibliography for 7155290--7155292.cif.'
_cod_database_code               7155291
_chemical_oxdiff_formula         'C18 H22 O3 N2 S1'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C30(H30A,
 H30B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C16(H16), C17(H17), C20(H20), C24(H24), C27(H27), C31(H31)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;