Rh-Catalyzed annulations of N-methoxybenzamides with ketenimines: synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties.
Zhou, Xiaorong; Peng, Zhixing; Zhao, Hongyang; Zhang, Zhiyin; Lu, Ping; Wang, Yanguang; Chemical communications (Cambridge, England) 52 (2016) 10676–10679; doi:10.1039/c6cc05456k

data_7124917
_publ_section_title
;
 Rh-Catalyzed annulations of N-methoxybenzamides with ketenimines:
 synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones
 with strong aggregation induced emission properties.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10676
_journal_page_last               10679
_journal_paper_doi               10.1039/c6cc05456k
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C44 H31 N O'
_chemical_formula_sum            'C44 H31 N O'
_chemical_formula_weight         589.70
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-21
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-11-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.871(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7155(5)
_cell_length_b                   11.1424(6)
_cell_length_c                   33.670(2)
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6043
_cell_measurement_theta_min      3.1049
_cell_volume                     3631.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0319913000
_diffrn_orient_matrix_UB_12      -0.0409325000
_diffrn_orient_matrix_UB_13      -0.0124688000
_diffrn_orient_matrix_UB_21      0.0439793000
_diffrn_orient_matrix_UB_22      -0.0198610000
_diffrn_orient_matrix_UB_23      0.0165994000
_diffrn_orient_matrix_UB_31      -0.0490555000
_diffrn_orient_matrix_UB_32      -0.0445124000
_diffrn_orient_matrix_UB_33      0.0040642000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14478
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_platon_squeeze_details
;
;
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1012P)^2^+0.2052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1950
_reflns_number_gt                4221
_reflns_number_total             6614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc05456k2.cif
_cod_data_source_block           151020_zxr454_013
_cod_database_code               7124917
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C14(H14), C15(H15),
 C17(H17), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37), C38(H38),
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;