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_7154098
_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 H25 F N2 O2), 0.5(C2 H4 Cl4)'
_chemical_formula_sum            'C51 H52 Cl2 F2 N4 O4'
_chemical_formula_weight         893.87
_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                 102.746(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.2842(10)
_cell_length_b                   11.1478(5)
_cell_length_c                   18.7003(12)
_cell_measurement_reflns_used    3240
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.9870
_cell_measurement_theta_min      3.3100
_cell_volume                     4531.0(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      100
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -90.00  -10.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000 -120.0000 80

  2 omega  -52.00   56.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   19.0000   90.0000 108

  3 omega   57.00   92.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  178.0000   30.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0019096000
_diffrn_orient_matrix_UB_12      -0.0288464000
_diffrn_orient_matrix_UB_13      0.0342037000
_diffrn_orient_matrix_UB_21      0.0217735000
_diffrn_orient_matrix_UB_22      0.0432605000
_diffrn_orient_matrix_UB_23      0.0171967000
_diffrn_orient_matrix_UB_31      -0.0242760000
_diffrn_orient_matrix_UB_32      0.0366581000
_diffrn_orient_matrix_UB_33      0.0066097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9553
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63950
_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_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+6.0441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1392
_reflns_number_gt                3619
_reflns_number_total             4641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01644k2.cif
_cod_data_source_block           wdh1024
_cod_depositor_comments
'Adding full bibliography for 7154096--7154099.cif.'
_cod_original_cell_volume        4531.1(4)
_cod_database_code               7154098
_chemical_oxdiff_formula         'C20 H10 N2 O3 F'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H12A,H12B} of C12, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H26A,H26B} of C26
2. Restrained distances
 C26-H26A = C26-H26B
 1.08 with sigma of 0.02
 H26A-H26B
 1.592 with sigma of 0.02
 Cl1-H26A = Cl1-H26B = Cl2-H26A = Cl2-H26B
 2.257 with sigma of 0.02
3. Rigid bond restraints
 Cl2, Cl1, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: C26(0.5) H26A(0.5) H26B(0.5) Cl1(0.5)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C8(H8), C2(H2A), C15(H15), C7(H7), C16(H16), C4(H4), C19(H19),
  C18(H18)
6.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C25(H25A,H25B,
 H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'