Exploring the original proposed biosynthesis of (+)-symbioimine: remote exocyclic stereocontrol in a type I IMDA reaction.
Burke, Jason P.; Sabat, Michal; Iovan, Diana A.; Myers, William H.; Chruma, Jason J.; Organic letters 12 (2010) 3192–3195; doi:10.1021/ol101141a

data_1503059
_publ_section_title
;
 Exploring the original proposed biosynthesis of (+)-symbioimine: remote
 exocyclic stereocontrol in a type I IMDA reaction.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3192
_journal_page_last               3195
_journal_paper_doi               10.1021/ol101141a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C26 H37 N O5'
_chemical_formula_sum            'C26 H37 N O5'
_chemical_formula_weight         443.57
_chemical_melting_point          373.15
_chemical_name_systematic
;
(3R,3aS,3a1R,4S,6aR,9aS)-tert-butyl 4-(3,5-dimethoxyphenyl)-9a-hydroxy-
3-methyl-2,3,3a,3a1,4,6a,7,8,9,9a-decahydro-1H-benzo[de]quinoline-1-carboxylate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5169(9)
_cell_length_b                   5.7641(3)
_cell_length_c                   50.954(3)
_cell_measurement_reflns_used    5282
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.301
_cell_measurement_theta_min      2.466
_cell_volume                     4851.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0906
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       75
_diffrn_reflns_limit_l_min       -76
_diffrn_reflns_number            60969
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9267
_exptl_absorpt_correction_T_min  0.8934
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         17435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.1501
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                6674
_reflns_number_total             17435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101141a_si_002.cif
_cod_data_source_block           C26H37NO5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        4851.1(4)
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               1503059