Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
Mercedes Amat; Carlos Ramos; Maria Perez; Elies Molins; Pedro Florindo; Maria M. M. Santos; Joan Bosch; Chemical communications (Cambridge, England) 49 (2013) 1954–1956; doi:10.1039/c2cc38540f

data_7108896
_publ_section_title
;
 Enantioselective formal synthesis of ent-rhynchophylline and
 ent-isorhynchophylline
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1954
_journal_page_last               1956
_journal_paper_doi               10.1039/c2cc38540f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H22 N2 O4'
_chemical_formula_sum            'C19 H22 N2 O4'
_chemical_formula_weight         342.39
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-07-22T11:33:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.56(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.372(8)
_cell_length_b                   6.401(3)
_cell_length_c                   14.653(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1805.1(15)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.09929
_diffrn_orient_matrix_UB_12      -0.093612
_diffrn_orient_matrix_UB_13      -0.011898
_diffrn_orient_matrix_UB_21      -0.004512
_diffrn_orient_matrix_UB_22      -0.03509
_diffrn_orient_matrix_UB_23      0.066231
_diffrn_orient_matrix_UB_31      -0.131188
_diffrn_orient_matrix_UB_32      -0.028519
_diffrn_orient_matrix_UB_33      -0.013972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3663
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.4
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.26
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_coef       0.0030(14)
_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   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     236
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.2214
_reflns_number_gt                2130
_reflns_number_total             3522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc38540f.txt
_cod_data_source_block           jb73y
_cod_original_cell_volume        1805.2(15)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7108896