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_4026254
_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 [3S,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           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 92.675(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2730(13)
_cell_length_b                   10.2509(14)
_cell_length_c                   11.609(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1221.2(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2306
_diffrn_reflns_theta_max         57.09
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    1.527
_exptl_absorpt_correction_type   'Semi-empirical from psi-scans'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0043(7)
_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_all   1.054
_refine_ls_goodness_of_fit_obs   1.053
_refine_ls_hydrogen_treatment    'riding atoms/rigid methyl groups'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         1948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_restrained_S_obs      1.053
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_obs          0.0370
_refine_ls_shift/esd_max         -0.021
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.1450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1028
_refine_ls_wR_factor_obs         0.0959
_reflns_number_observed          1735
_reflns_number_total             1948
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo200191c_si_005.cif
_cod_data_source_block           syn_21a_endo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+0.1450P] 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^)+(0.0639P)^2^+0.1450P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4026254