Synthesis of the isoquinocycline-pyrrolopyrrole substructure.
Cordes, Jens; Harms, Klaus; Koert, Ulrich; Organic letters 12 (2010) 3808–3811; doi:10.1021/ol101500k

data_1503137
_publ_section_title
;
 Synthesis of the isoquinocycline-pyrrolopyrrole substructure.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3808
_journal_page_last               3811
_journal_paper_doi               10.1021/ol101500k
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H14 O4'
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-06-25T12:24:17-00:00
_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                   11.0204(5)
_cell_length_b                   8.2388(5)
_cell_length_c                   12.1197(6)
_cell_measurement_reflns_used    6946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1.6
_cell_measurement_wavelength     0.71073
_cell_volume                     1100.41(10)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-AREA'
_computing_molecular_graphics    'DIAMOND 3.1 (Brandenburg, 1999)'
_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_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5278
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.7
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0017
_exptl_absorpt_correction_T_min  0.9392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 in PLATON      
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.138
_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   -0.4(6)
_refine_ls_extinction_coef       0.036(3)
_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   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0235
_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^)+(0.0425P)^2^+0.0267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0591
_reflns_number_gt                2090
_reflns_number_total             2185
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol101500k_si_001.cif
_cod_data_source_block           14
_cod_database_code               1503137