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_7154097
_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         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-18
_audit_creation_method
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Olex2 1.2
(compiled 2014.05.21 svn.r2942 for OlexSys, GUI svn.r4846)
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_cell_measurement_theta_min      3.2990
_cell_volume                     1041.82(11)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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_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)
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_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      100
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
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  1 omega   -6.00   84.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   70.0000 -146.0000 90

  2 omega  -50.00   45.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -70.0000   82.0000 95

  3 omega  -13.00   22.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  -30.0000 35

  4 omega  -13.00   33.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -57.0000  -30.0000 46

  5 omega   -3.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   38.0000    0.0000 93
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_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
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_diffrn_orient_matrix_UB_21      -0.0152995000
_diffrn_orient_matrix_UB_22      -0.0444874000
_diffrn_orient_matrix_UB_23      -0.0267850000
_diffrn_orient_matrix_UB_31      0.0557535000
_diffrn_orient_matrix_UB_32      -0.0513034000
_diffrn_orient_matrix_UB_33      0.0390808000
_diffrn_radiation_monochromator  mirror
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_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7439
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
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_exptl_absorpt_coefficient_mu    0.076
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_exptl_absorpt_correction_T_min  0.97027
_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.
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_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
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_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_gt           0.0429
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.5514P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
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_reflns_number_gt                3535
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01644k2.cif
_cod_data_source_block           wdh1023
_cod_depositor_comments
'Adding full bibliography for 7154096--7154099.cif.'
_cod_original_cell_volume        1041.81(11)
_cod_database_code               7154097
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C20 H10 N2 O3'
_reflns_odcompleteness_completeness 99.88
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C8(H8), C16(H16), C15(H15), C18(H18), C17(H17), C4(H4),
 C7(H7), C2(H2A), C3(H3), C5(H5)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              82842
_olex2_submission_special_instructions 'No special instructions were received'