Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton
Ahmad, Sajjad; Swift, Michael D.; Farrugia, Louis J.; Senn, Hans Martin; Sutherland, Andrew; Organic & Biomolecular Chemistry 10 (2012) 3937–; doi:10.1039/c2ob25334h

data_7152336
_publ_section_title
;
 Stereoselective synthesis of functionalised carbocyclic amides:
 construction of the syn-(4aS,10bS)-phenanthridone skeleton
;
_journal_issue                   19
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3937
_journal_paper_doi               10.1039/c2ob25334h
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H15 N O6'
_chemical_formula_sum            'C14 H15 N O6'
_chemical_formula_weight         293.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_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             2011-09-22T13:16:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5782(4)
_cell_length_b                   8.7302(5)
_cell_length_c                   21.2398(12)
_cell_measurement_reflns_used    5726
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.8778
_cell_measurement_theta_min      3.242
_cell_measurement_wavelength     0.71073
_cell_volume                     1219.78(12)
_computing_cell_refinement       'SAINT integration routine (Bruker, 2007)'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.110689
_diffrn_orient_matrix_UB_12      -0.29047E-1
_diffrn_orient_matrix_UB_13      -0.299812E-1
_diffrn_orient_matrix_UB_21      -0.897725E-1
_diffrn_orient_matrix_UB_22      0.274369E-1
_diffrn_orient_matrix_UB_23      -0.362828E-1
_diffrn_orient_matrix_UB_31      0.528948E-1
_diffrn_orient_matrix_UB_32      0.10735
_diffrn_orient_matrix_UB_33      0.11609E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16471
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.21
_diffrn_reflns_theta_max         27.21
_diffrn_reflns_theta_min         1.92
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0405P)^2^+0.4126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                1493
_reflns_number_total             1603
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c2ob25334h.txt
_cod_data_source_block           shelx
_cod_database_code               7152336