Oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine.
Liu, Xiao-Yu; Cheng, Hang; Li, Xiao-Huan; Chen, Qiao-Hong; Xu, Liang; Wang, Feng-Peng; Organic & biomolecular chemistry 10 (2012) 1411–1417; doi:10.1039/c1ob06704d

data_7152195
_publ_section_title
;
 Oxidative dearomatization/intramolecular Diels-Alder cycloaddition
 cascade for the syntheses of (+-)-atisine and (+-)-isoazitine.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1411
_journal_page_last               1417
_journal_paper_doi               10.1039/c1ob06704d
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C22 H33 N O2'
_chemical_formula_sum            'C22 H33 N O2'
_chemical_formula_weight         343.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-07-16
_audit_creation_method
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4693(8)
_cell_length_b                   19.713(3)
_cell_length_c                   22.265(2)
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    291.15
_cell_measurement_theta_max      66.9667
_cell_measurement_theta_min      2.9927
_cell_volume                     3717.3(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega -29.00 18.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 0.0000 77.0000 120.0000 47

2 omega 35.00 69.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 0.0000 77.0000 120.0000 34

3 omega -95.00 -62.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -42.5000 -50.0000 -180.0000 33

4 omega -83.00 -47.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -42.5000 -162.0000 -76.0000 36

5 omega -51.00 26.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -42.5000 25.0000 -150.0000 77

6 omega 86.00 124.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 55.8596 162.0000 -48.0000 38

7 omega -5.00 84.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 55.8596 -77.0000 60.0000 89

8 omega 40.00 93.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -25.0000 -30.0000 53

9 omega 43.00 80.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -117.0000 73.0000 37

10 omega 45.00 104.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -50.0000 90.0000 59

11 omega 45.00 94.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -25.0000 90.0000 49

12 omega 60.00 118.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -119.0000 -71.0000 58

13 omega 43.00 70.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -25.0000 -180.0000 27

14 omega 41.00 88.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -25.0000 30.0000 47

15 omega 110.00 143.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 162.0000 -48.0000 33

16 omega 42.00 104.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 -50.0000 -180.0000 62

17 omega 91.00 178.00 1.0000 60.0000
omega____ theta____ kappa____ phi______ frames
- 111.7191 0.0000 0.0000 87

18 omega -30.00 70.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 0.0000 77.0000 -90.0000 100

19 omega 26.00 77.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 55.8596 77.0000 60.0000 51
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0389296000
_diffrn_orient_matrix_UB_12      -0.0677163000
_diffrn_orient_matrix_UB_13      0.0313614000
_diffrn_orient_matrix_UB_21      0.0140941000
_diffrn_orient_matrix_UB_22      0.0371598000
_diffrn_orient_matrix_UB_23      0.0606369000
_diffrn_orient_matrix_UB_31      -0.1771911000
_diffrn_orient_matrix_UB_32      -0.0118518000
_diffrn_orient_matrix_UB_33      0.0116758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12837
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.97
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0688P)^2^+0.7129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                2623
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06704d.txt
_cod_data_source_block           201107110
_cod_original_cell_volume        3717.2(7)
_cod_database_code               7152195
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97