Stereoselective synthesis of aminoindanols via an efficient cascade aza-Michael-aldol reaction
Hui Qian; Wanxiang Zhao; Herman H-Y. Sung; Ian D. Williams; Jianwei Sun; Chem.Commun. 49 (2013) 4361–; doi:10.1039/c2cc37102b

data_7109223
_publ_section_title
;
 Stereoselective synthesis of aminoindanols via an efficient cascade
 aza-Michael-aldol reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              4361
_journal_paper_doi               10.1039/c2cc37102b
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_symmetry_cell_setting           orthorhombic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled May 9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.687
_cell_length_b                   10.66360(10)
_cell_length_c                   29.8209(2)
_cell_measurement_reflns_used    9561
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      71.3734
_cell_measurement_theta_min      4.1423
_cell_volume                     1808.46(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.9909
_diffrn_measured_fraction_theta_max 0.9909
_diffrn_measurement_details
;
1 omega 38.00 66.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 -60.0000 35

2 omega 41.00 74.60 0.8000 1.0000
omega____ theta____ kappa____ phi______ frames
- 0.0000 -178.0000 90.0000 42

3 omega 38.00 122.00 0.8000 5.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 57.0000 30.0000 105

4 omega 34.00 82.00 0.8000 5.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 -77.0000 30.0000 60

5 omega 78.00 123.60 0.8000 5.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 57.0000 -60.0000 57

6 omega -14.00 18.80 0.8000 5.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 -57.0000 150.0000 41

7 omega -14.00 79.60 0.8000 5.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 -77.0000 -90.0000 117

8 omega -47.00 5.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- -64.0000 25.0000 150.0000 65

9 omega 101.00 147.40 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -92.0000 0.0000 58

10 omega 38.00 70.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 -150.0000 40

11 omega 126.00 166.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 64.0000 120.0000 50

12 omega 42.00 69.20 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 0.0000 34

13 omega 39.00 84.60 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -92.0000 0.0000 57

14 omega 40.00 65.60 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 -90.0000 32

15 omega 37.00 69.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 90.0000 40

16 omega 44.00 68.80 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 -30.0000 31

17 omega 41.00 69.80 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 -120.0000 36

18 omega 39.00 67.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 -180.0000 35

19 omega 37.00 65.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 120.0000 35

20 omega 46.00 142.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -92.0000 150.0000 120

21 omega 52.00 144.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -92.0000 -60.0000 115

22 omega 87.00 119.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 64.0000 120.0000 40

23 omega 48.00 81.60 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 30.0000 42

24 omega 38.00 70.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -38.0000 150.0000 40

25 omega 48.00 172.00 0.8000 15.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 0.0000 -60.0000 155
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2182176000
_diffrn_orient_matrix_UB_12      -0.0610783000
_diffrn_orient_matrix_UB_13      -0.0214651000
_diffrn_orient_matrix_UB_21      -0.0196599000
_diffrn_orient_matrix_UB_22      -0.1106800000
_diffrn_orient_matrix_UB_23      0.0329818000
_diffrn_orient_matrix_UB_31      -0.1593801000
_diffrn_orient_matrix_UB_32      -0.0699656000
_diffrn_orient_matrix_UB_33      -0.0334496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9437
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         4.40
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35
_diffrn_source_power             1.75
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.2368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                3166
_reflns_number_total             3171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc37102b.txt
_cod_data_source_block           qian5cult
_cod_original_cell_volume        1808.42(2)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7109223
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13