Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp(2)-H functionalization.
Ambasana, Pratik A.; Vachhani, Dipak D.; Galli, Marzia; Jacobs, Jeroen; Van Meervelt, Luc; Shah, Anamik K.; Van der Eycken, Erik V.; Organic & biomolecular chemistry 12 (2014) 8861–8865; doi:10.1039/c4ob01644k

data_7154096
_publ_section_title
;
 Solvent switchable cycloaddition: a (one-pot) metal-free approach towards
 N-substituted benzo[e]- or [f]isoindolones via Csp(2)-H
 functionalization.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8861
_journal_page_last               8865
_journal_paper_doi               10.1039/c4ob01644k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         '2(C25 H26 N2 O2), 0.5(C2 H8 O2)'
_chemical_formula_sum            'C51 H56 N4 O5'
_chemical_formula_weight         805.00
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.275(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.4413(9)
_cell_length_b                   10.7973(6)
_cell_length_c                   18.1182(9)
_cell_measurement_reflns_used    3426
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.6850
_cell_measurement_theta_min      3.3480
_cell_volume                     4289.8(4)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -36.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   38.0000 -180.0000 61

  2 omega  -80.00   34.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000  -60.0000 114

  3 omega   63.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  178.0000  150.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0125376000
_diffrn_orient_matrix_UB_12      0.0300207000
_diffrn_orient_matrix_UB_13      0.0280315000
_diffrn_orient_matrix_UB_21      -0.0133350000
_diffrn_orient_matrix_UB_22      0.0453398000
_diffrn_orient_matrix_UB_23      -0.0267471000
_diffrn_orient_matrix_UB_31      -0.0267027000
_diffrn_orient_matrix_UB_32      -0.0368165000
_diffrn_orient_matrix_UB_33      -0.0101123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8361
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85682
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0357P)^2^+4.5957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                3602
_reflns_number_total             4392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01644k2.cif
_cod_data_source_block           wdh1022
_cod_depositor_comments
'Adding full bibliography for 7154096--7154099.cif.'
_cod_database_code               7154096
_chemical_oxdiff_formula         'C20 H10 N2 O3'
_reflns_odcompleteness_completeness 99.81
_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, All O(H) groups
2. Restrained distances
 O3-C27
 1.414 with sigma of 0.002
3. Others
 Fixed Sof: O3(0.5) H3A(0.5) H27A(0.5) H27B(0.5) H27C(0.5)
 Fixed X: H3A(0.4885) H27A(0.4878) H27B(0.548301) H27C(0.48829)
 Fixed Y: H3A(0.3069) H27A(0.1808) H27B(0.1965) H27C(0.114429)
 Fixed Z: H3A(0.665501) H27A(0.7997) H27B(0.763) H27C(0.72086)
4.a Ternary CH refined with riding coordinates:
 C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C21(H21), C22(H22),
 C24(H24), C25(H25)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C26(H26A,H26B,
 H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'