Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinoline Derivatives by 1,3-Dipolar Cycloadditions of Stabilized Isoquinolinium N-Ylides with Sulfinyl Dipolarophiles
José Luis García Ruano; Alberto Fraile; M. Rosario Martín; Gemma González; Cristina Fajardo; Ana María Martín-Castro; Journal of Organic Chemistry 76 (2011) 3296–3305; doi:10.1021/jo200191c

data_4026252
_publ_section_title
;
 Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinoline Derivatives by
 1,3-Dipolar Cycloadditions of Stabilized Isoquinolinium N-Ylides with
 Sulfinyl Dipolarophiles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3296
_journal_page_last               3305
_journal_paper_doi               10.1021/jo200191c
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C26 H27 N O6 S'
_chemical_formula_weight         481.55
_space_group_IT_number           19
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5083(5)
_cell_length_b                   17.6294(10)
_cell_length_c                   18.7013(10)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      46.10
_cell_measurement_theta_min      3.43
_cell_volume                     2475.4(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2527
_diffrn_reflns_theta_full        56.99
_diffrn_reflns_theta_max         56.99
_diffrn_reflns_theta_min         3.45
_diffrn_standards_interval_count 47
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  0.3427
_exptl_absorpt_correction_T_min  0.2667
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            TRANSPARENT
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       PARALELEPIPEDO
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.4321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2109
_reflns_number_total             2340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200191c_si_003.cif
_cod_data_source_block           ana21
_cod_database_code               4026252