Environmentally benign access to isoindolinones: synthesis, separation and resource recycling
Guo, Weiwei; Zhang, Qi; Cao, Yang; Cai, Kaihua; Zhang, Shengyong; Chai, Yonghai; Green Chemistry 22 (2020) 2873–2878; doi:10.1039/D0GC00957A

data_7240295
_publ_section_title
;
 Environmentally benign access to isoindolinones: synthesis, separation
 and resource recycling
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2873
_journal_page_last               2878
_journal_paper_doi               10.1039/D0GC00957A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2020-01-15 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                105.854(5)
_cell_angle_beta                 90.015(6)
_cell_angle_gamma                94.640(6)
_cell_formula_units_Z            2
_cell_length_a                   4.1648(3)
_cell_length_b                   10.9613(6)
_cell_length_c                   12.0440(7)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9700
_cell_measurement_theta_min      4.1930
_cell_volume                     527.04(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
  1 omega    3.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 58

  2 omega   -2.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 42

  3 omega   39.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 25

  4 omega  -17.00   81.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -37.0000  150.0000 98

  5 omega   -3.00   62.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000  150.0000 65

  6 omega   57.00  113.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000  -60.0000 56

  7 omega   30.00  119.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   37.0000  -30.0000 89

  8 omega    6.00   48.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -30.0000 42

  9 omega  -11.00   62.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000   30.0000 73

 10 omega   45.00  123.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -91.0000  150.0000 78

 11 omega   75.00  104.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000  150.0000 29

 12 omega   48.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  120.0000 44

 13 omega  117.00  166.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -180.0000 49

 14 omega   49.00   87.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  150.0000 38

 15 omega   78.00  109.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -180.0000 31

 16 omega  124.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   60.0000 54

 17 omega   42.00   82.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -60.0000 40

 18 omega   87.00  115.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   60.0000 28

 19 omega   40.00   85.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 45

 20 omega   40.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -120.0000 52

 21 omega   51.00  136.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000    0.0000 85

 22 omega   71.00  116.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  -60.0000 45

 23 omega   49.00   83.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   30.0000 34

 24 omega   43.00   70.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   90.0000 27

 25 omega   47.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000    0.0000 45

 26 omega  140.00  174.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  111.0000   90.0000 34

 27 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 100

 28 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 100

 29 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -120.0000 101

 30 omega  -13.00   76.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -90.0000 89

 31 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   60.0000 101

 32 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  120.0000 90

 33 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -150.0000 90

 34 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000   30.0000 90

 35 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000  -60.0000 97

 36 omega   41.00  105.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000  -60.0000 64

 37 omega   89.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000    0.0000 89

 38 omega   85.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   90.0000 93

 39 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000 -180.0000 97

 40 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000 -150.0000 97

 41 omega   77.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -150.0000 101

 42 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000    0.0000 97

 43 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000  -90.0000 97

 44 omega   39.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   12.0000  -30.0000 139

 45 omega   39.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 53

 46 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000   90.0000 97

 47 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -150.0000 98

 48 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 90

 49 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -30.0000 101

 50 omega   25.00   86.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  150.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0032607000
_diffrn_orient_matrix_UB_12      0.0650656000
_diffrn_orient_matrix_UB_13      0.1306508000
_diffrn_orient_matrix_UB_21      0.0227520000
_diffrn_orient_matrix_UB_22      0.1313052000
_diffrn_orient_matrix_UB_23      -0.0242450000
_diffrn_orient_matrix_UB_31      -0.3705023000
_diffrn_orient_matrix_UB_32      -0.0048732000
_diffrn_orient_matrix_UB_33      -0.0057468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.329
_diffrn_reflns_theta_min         3.816
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             228
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0908P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1620
_reflns_number_total             2037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00957a2.cif
_cod_data_source_block           exp_11203
_cod_depositor_comments
;Adding full bibliography for 7240295.cif.

 Adding full bibliography for 7240295.cif.
;
_cod_database_code               7240295
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'Br C O'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'