Synthesis of Isoindoles from Intramolecular Condensation of Benzyl Azides with α-Aryldiazoesters.
Zhu, Jing; Li, Rui; Su, Yan; Gu, Peiming; The Journal of organic chemistry 84 (2019) 5813–5820; doi:10.1021/acs.joc.8b03180

data_4034367
_publ_section_title
;
 Synthesis of Isoindoles from Intramolecular Condensation of Benzyl Azides
 with \a-Aryldiazoesters.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5813
_journal_page_last               5820
_journal_paper_doi               10.1021/acs.joc.8b03180
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.381(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.394(3)
_cell_length_b                   7.2723(8)
_cell_length_c                   14.8685(13)
_cell_measurement_reflns_used    963
_cell_measurement_temperature    293.39(10)
_cell_measurement_theta_max      24.0850
_cell_measurement_theta_min      3.9490
_cell_volume                     2841.4(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.39(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -15.00   22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -150.0000 37

  2 omega   77.00  102.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000  -60.0000 25

  3 omega  -46.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   60.0000 112

  4 omega   44.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000   60.0000 61
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0258561000
_diffrn_orient_matrix_UB_12      -0.0225907000
_diffrn_orient_matrix_UB_13      0.0040847000
_diffrn_orient_matrix_UB_21      0.0063678000
_diffrn_orient_matrix_UB_22      -0.0946793000
_diffrn_orient_matrix_UB_23      0.0013001000
_diffrn_orient_matrix_UB_31      0.0046182000
_diffrn_orient_matrix_UB_32      0.0045947000
_diffrn_orient_matrix_UB_33      0.0477145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5250
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.6369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                1656
_reflns_number_total             2778
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b03180_si_002.cif
_cod_data_source_block           zhangye_1107
_cod_database_code               4034367
_reflns_odcompleteness_completeness 99.59
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2017-11-08
_olex2_submission_special_instructions 'No special instructions were received'