Rh(III)-catalyzed annulation of N-methoxybenzamides with ynesulfonamides at room temperature: a practical and efficient route to 4-aminoisoquinolone derivatives
Tan, Guangying; Huang, Xiaolei; Wu, Qian; Zhang, Luo-Qiang; You, Jingsong; RSC Adv.  (2014) –; doi:10.1039/C4RA09500F

data_7218171
_publ_section_title
;
 Rh(III)-catalyzed annulation of N-methoxybenzamides with ynesulfonamides
 at room temperature: a practical and efficient route to
 4-aminoisoquinolone derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA09500F
_journal_year                    2014
_chemical_formula_moiety         'C28 H22 N2 O3 S'
_chemical_formula_sum            'C28 H22 N2 O3 S'
_chemical_formula_weight         466.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-25
_audit_creation_method
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Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
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_cell_angle_alpha                90
_cell_angle_beta                 104.175(5)
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_cell_length_a                   11.8493(6)
_cell_length_b                   11.0311(5)
_cell_length_c                   18.2794(7)
_cell_measurement_reflns_used    3038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3230
_cell_measurement_theta_min      3.7030
_cell_volume                     2316.57(19)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -88.00  -57.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000   60.0000 31

  2 omega  -23.00   17.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  -90.0000 40

  3 omega   47.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  178.0000  -30.0000 40

  4 omega  -34.00   92.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580    0.0000   30.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0576960000
_diffrn_orient_matrix_UB_12      -0.0044691000
_diffrn_orient_matrix_UB_13      0.0044051000
_diffrn_orient_matrix_UB_21      -0.0062780000
_diffrn_orient_matrix_UB_22      -0.0571161000
_diffrn_orient_matrix_UB_23      -0.0183967000
_diffrn_orient_matrix_UB_31      0.0211278000
_diffrn_orient_matrix_UB_32      -0.0291622000
_diffrn_orient_matrix_UB_33      0.0352678000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.949
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
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_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.3358P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                3470
_reflns_number_total             4722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra09500f2.cif
_cod_data_source_block           140225_s2_tgy
_cod_original_cell_volume        2316.58(18)
_cod_database_code               7218171
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n1o3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), N1(H1)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              93795
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'