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_4026253
_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
_chemical_name_systematic
; 
 Ethyl [3R,3aS,4S,11bR,11cS,(S)S]-3-Ethoxy-11c-p-tolylsulfinyl
-1-oxo-3a,4,11b,11c-tetrahydro-1H,3H-furo[3',4':3,4]pyrrolo[2,1-a]
isoquinoline-4-carboxylate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0923(5)
_cell_length_b                   15.3412(6)
_cell_length_c                   17.4219(9)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      3.83
_cell_volume                     2430.1(2)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       'Siemens 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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2482
_diffrn_reflns_theta_max         57.14
_diffrn_reflns_theta_min         3.84
_diffrn_standards_interval_count 47
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.534
_exptl_absorpt_correction_type   'Semi-empirical from psi scans'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.193
_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   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.049
_refine_ls_goodness_of_fit_obs   1.060
_refine_ls_hydrogen_treatment    'riding atoms/rigid methyl groups'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_restrained_S_obs      1.060
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_obs          0.0395
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1019
_refine_ls_wR_factor_obs         0.0927
_reflns_number_observed          1896
_reflns_number_total             2273
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo200191c_si_004.cif
_cod_data_source_block           anti_21b_endo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0986P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0986P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4026253