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_7109222
_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 H19 N O2 S'
_chemical_formula_sum            'C20 H19 N O2 S'
_chemical_formula_weight         337.42
_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             2012-09-07
_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                   5.2087(2)
_cell_length_b                   10.6761(4)
_cell_length_c                   31.3923(11)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      71.8827
_cell_measurement_theta_min      4.1364
_cell_volume                     1745.68(11)
_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 0.9715
_diffrn_measured_fraction_theta_max 0.9715
_diffrn_measurement_details
;
1 omega 124.00 149.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 -25.0000 30.0000 25

2 omega 17.00 43.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 0.0000 -99.0000 -180.0000 26

3 omega -24.00 6.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 0.0000 -99.0000 -180.0000 30

4 omega 88.00 128.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 57.0000 125.0000 -150.0000 40

5 omega 74.00 128.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 57.0000 125.0000 60.0000 54

6 omega 77.00 122.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 57.0000 125.0000 150.0000 45

7 omega 81.00 107.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 57.0000 84.0000 -34.0000 26

8 omega -155.00 -135.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -86.0000 -111.0000 120.0000 20

9 omega 61.00 157.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 145.0000 19.0000 96

10 omega 45.00 71.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 -38.0000 -90.0000 26

11 omega 88.00 178.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 50.0000 -150.0000 90

12 omega -72.00 33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 0.0000 -77.0000 -60.0000 105

13 omega -130.00 -26.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -57.0000 -38.0000 150.0000 104

14 omega -128.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -57.0000 -57.0000 60.0000 95

15 omega -128.00 -87.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -57.0000 -57.0000 -60.0000 41

16 omega -116.00 -12.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -86.0000 111.0000 120.0000 104

17 omega 124.00 158.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 -25.0000 60.0000 34

18 omega 41.00 52.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 114.0000 -38.0000 -120.0000 11
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2934083000
_diffrn_orient_matrix_UB_12      0.0164313000
_diffrn_orient_matrix_UB_13      0.0031959000
_diffrn_orient_matrix_UB_21      0.0329559000
_diffrn_orient_matrix_UB_22      -0.0675525000
_diffrn_orient_matrix_UB_23      -0.0430659000
_diffrn_orient_matrix_UB_31      -0.0201131000
_diffrn_orient_matrix_UB_32      0.1263999000
_diffrn_orient_matrix_UB_33      -0.0232876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6109
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.37
_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    1.733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60637
_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            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0320P)^2^+0.9625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2721
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc37102b.txt
_cod_data_source_block           qian4cult
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7109222
_reflns_odcompleteness_completeness 97.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13