Formal Aromatic C-H Insertion for Stereoselective Isoquinolinone Synthesis and Studies on Mechanistic Insights into the C-C Bond Formation
Chan Pil Park; Advait Nagle; Cheol Hwan Yoon; Chiliu Chen; Kyung Woon Jung; Journal of Organic Chemistry 74 (2009) 6231–6236; doi:10.1021/jo9011255

data_4024776
_publ_section_title
;
Formal Aromatic C-H Insertion for Stereoselective Isoquinolinone
Synthesis and Studies on Mechanistic Insights into the C-C Bond Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6231
_journal_page_last               6236
_journal_paper_doi               10.1021/jo9011255
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 93.0850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4804(7)
_cell_length_b                   15.2981(11)
_cell_length_c                   11.7776(8)
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.18
_cell_volume                     1705.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      135(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10258
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9080
_exptl_absorpt_correction_T_min  0.8146
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.71
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.4715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3540
_reflns_number_total             3819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011255_si_002.cif
_cod_data_source_block           vic1m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024776