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_7154099
_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         'C25 H26 N2 O2'
_chemical_formula_sum            'C25 H26 N2 O2'
_chemical_formula_weight         386.48
_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)
;
_cell_angle_alpha                87.087(6)
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_cell_formula_units_Z            4
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_cell_length_b                   13.5350(10)
_cell_length_c                   13.8969(10)
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.0040
_cell_measurement_theta_min      3.0560
_cell_volume                     2126.3(3)
_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)
;
_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      100
_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  -39.00   13.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   58.0000  -91.0000 52

  2 omega  -10.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000   30.0000 32

  3 omega  -33.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000   30.0000 80

  4 omega  -13.00   24.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  -90.0000 37

  5 omega   -3.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  150.0000 25

  6 omega  -54.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000 -180.0000 101

  7 omega  -70.00    0.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  120.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_13      0.0242310000
_diffrn_orient_matrix_UB_21      -0.0526774000
_diffrn_orient_matrix_UB_22      -0.0116731000
_diffrn_orient_matrix_UB_23      0.0351341000
_diffrn_orient_matrix_UB_31      -0.0016060000
_diffrn_orient_matrix_UB_32      -0.0384756000
_diffrn_orient_matrix_UB_33      -0.0321514000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0378
_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       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16637
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.954
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85415
_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    1.207
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
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_refine_diff_density_max         0.224
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_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         8666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+1.0885P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
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_reflns_number_gt                6908
_reflns_number_total             8666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01644k2.cif
_cod_data_source_block           wdh1025
_cod_depositor_comments
'Adding full bibliography for 7154096--7154099.cif.'
_cod_database_code               7154099
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C20 H10 N2 O3 F'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
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_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), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4A), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C15(H15),
 C16(H16), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
  C35(H35), C40(H40), C41(H41), C43(H43), C44(H44)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C)
;
_shelx_res_checksum              62069
_olex2_submission_special_instructions 'No special instructions were received'