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_7109224
_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_formula_moiety         'C11 H10 N2 O2 S'
_chemical_formula_sum            'C11 H10 N2 O2 S'
_chemical_formula_weight         234.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-09-28
_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                 104.158(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0959(6)
_cell_length_b                   7.5933(3)
_cell_length_c                   20.2857(8)
_cell_measurement_reflns_used    3712
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      71.5126
_cell_measurement_theta_min      9.7490
_cell_volume                     2105.32(15)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
1 omega 46.00 83.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 90.0000 37

2 omega 79.00 118.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 125.0000 -60.0000 39

3 omega 73.00 122.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 125.0000 0.0000 49

4 omega 36.00 123.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 57.0000 0.0000 87

5 omega -17.00 71.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 -38.0000 30.0000 88

6 omega 141.00 168.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 12.0000 -180.0000 27

7 omega 89.00 162.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 50.0000 -120.0000 73

8 omega 84.00 157.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 38.0000 30.0000 73

9 omega 45.00 87.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -111.0000 60.0000 42

10 omega 40.00 71.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 -120.0000 31

11 omega 39.00 65.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -48.0000 -63.0000 26

12 omega 64.00 102.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 12.0000 -180.0000 38

13 omega 41.00 86.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -111.0000 -30.0000 45

14 omega 44.00 140.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -77.0000 90.0000 96

15 omega 34.00 112.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 57.0000 90.0000 78

16 omega 25.00 125.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 77.0000 150.0000 100
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0108717000
_diffrn_orient_matrix_UB_12      -0.1174984000
_diffrn_orient_matrix_UB_13      0.0633656000
_diffrn_orient_matrix_UB_21      -0.1120860000
_diffrn_orient_matrix_UB_22      -0.0214332000
_diffrn_orient_matrix_UB_23      -0.0156327000
_diffrn_orient_matrix_UB_31      0.0066378000
_diffrn_orient_matrix_UB_32      -0.1646828000
_diffrn_orient_matrix_UB_33      -0.0432290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7985
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         10.04
_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    2.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45580
_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    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0961P)^2^+1.7503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                3336
_reflns_number_total             3575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc37102b.txt
_cod_data_source_block           qian6cult
_cod_original_cell_volume        2105.31(15)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7109224
_reflns_odcompleteness_completeness 98.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13