Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids
Li, Yiming; Wang, Yuhong; Yang, Tilong; Lin, Zhenyang; Jiang, Xuefeng; Green Chemistry 23 (2021) 2986–2991; doi:10.1039/D0GC04407E

data_7242298
_publ_section_title
;
 Selenium-catalyzed intramolecular atom- and redox-economical
 transformation of o-nitrotoluenes into anthranilic acids
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2986
_journal_page_last               2991
_journal_paper_doi               10.1039/D0GC04407E
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H26 N2 O4'
_chemical_formula_sum            'C17 H26 N2 O4'
_chemical_formula_weight         322.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-18 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.90480(10)
_cell_length_b                   11.22760(10)
_cell_length_c                   19.3205(2)
_cell_measurement_reflns_used    28585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1190
_cell_measurement_theta_min      4.5450
_cell_volume                     1714.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -29.00  31.00   1.00    1.00    --    0.00  77.00 -82.00   60
  2  \w     65.00 113.00   1.00    1.00    --   95.80  77.00 -82.00   48
  3  \w     38.00 126.00   1.00    1.00    --   95.80 -77.00 151.00   88
  4  \w      8.00  36.00   1.00    1.00    --   95.80 -77.00 151.00   28
  5  \w     36.00  85.00   1.00    1.00    --    0.00  77.00 -82.00   49
  6  \w     14.00  89.00   1.00    1.00    --    0.00  38.00   0.00   75
  7  \w     46.00  78.00   1.00    1.00    --    0.00  57.00-120.00   32
  8  \w    -84.00 -59.00   1.00    1.00    --    0.00 -77.00 151.00   25
  9  \w    -17.00  12.00   1.00    1.00    --    0.00  57.00   0.00   29
 10  \w    -84.00  20.00   1.00    1.00    --    0.00 -57.00  60.00  104
 11  \w    -18.00  15.00   1.00    1.00    --    0.00  38.00-150.00   33
 12  \w     36.00  61.00   1.00    1.00    --    0.00  57.00   0.00   25
 13  \w     17.00  87.00   1.00    1.00    --    0.00  38.00  90.00   70
 14  \w    -22.00  88.00   1.00    1.00    --    0.00  57.00 150.00  110
 15  \w    -19.00   6.00   1.00    1.00    --    0.00  38.00  90.00   25
 16  \w    -33.00  27.00   1.00    1.00    --    0.00 -77.00 151.00   60
 17  \w    -23.00  40.00   1.00    1.00    --    0.00  57.00-120.00   63
 18  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 19  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 20  \w     71.00  97.00   1.00    1.00    --   95.80  61.00 120.00   26
 21  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 22  \w     72.00 184.00   1.00    1.00    --   95.80  56.00 -94.02  112
 23  \w     71.00 164.00   1.00    1.00    --   95.80  61.00 150.00   93
 24  \w    111.00 185.00   1.00    1.00    --   95.80  82.00-120.00   74
 25  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 26  \w    144.00 179.00   1.00    1.00    --   95.80  77.00  17.74   35
 27  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 28  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 29  \w    113.00 139.00   1.00    1.00    --   95.80  77.00  60.00   26
 30  \w     68.00 171.00   1.00    1.00    --   95.80  70.00-123.30  103
 31  \w     65.00 105.00   1.00    1.00    --   95.80  77.00  -5.61   40
 32  \w     65.00 107.00   1.00    1.00    --   95.80  77.00-180.00   42
 33  \w    101.00 127.00   1.00    1.00    --   95.80  82.00-150.00   26
 34  \w     73.00 138.00   1.00    1.00    --   95.80  61.00  90.00   65
 35  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  17.74   25
 36  \w     71.00 110.00   1.00    1.00    --   95.80  59.00 166.93   39
 37  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 39  \w     73.00 185.00   1.00    1.00    --   95.80  53.00  -5.60  112
 40  \w    150.00 179.00   1.00    1.00    --   95.80  82.00 -30.00   29
 41  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 42  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 43  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 44  \w     74.00 107.00   1.00    1.00    --   95.80  49.00  61.49   33
 45  \w    113.00 184.00   1.00    1.00    --   95.80  49.00  61.49   71
 46  \w     71.00 112.00   1.00    1.00    --   95.80  61.00  60.00   41
 47  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 48  \w    157.00 182.00   1.00    1.00    --   95.80  77.00 -60.00   25
 49  \w     23.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00  105
 50  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 51  \w    148.00 177.00   1.00    1.00    --   95.80  82.00 150.00   29
 52  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 53  \w     12.00  38.00   1.00    1.00    --   95.80 -82.00-120.00   26
 54  \w     56.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   70
 55  \w     75.00 179.00   1.00    1.00    --   95.80  45.00 -30.00  104
 56  \w     78.00 105.00   1.00    1.00    --   95.80  45.00 150.00   27
 57  \w    122.00 148.00   1.00    1.00    --   95.80  45.00 150.00   26
 58  \w     75.00 100.00   1.00    1.00    --   95.80  52.00 110.64   25
 59  \w      6.00  50.00   1.00    1.00    --   95.80 -82.00  90.00   44
 60  \w     58.00 125.00   1.00    1.00    --   95.80 -82.00  90.00   67
 61  \w    145.00 170.00   1.00    1.00    --   95.80  72.00 -96.83   25
 62  \w     69.00 157.00   1.00    1.00    --   95.80  66.00-150.04   88
 63  \w    138.00 183.00   1.00    1.00    --   95.80  82.00  90.00   45
 64  \w     67.00  92.00   1.00    1.00    --   95.80  72.00 -96.83   25
 65  \w    116.00 183.00   1.00    1.00    --   95.80  61.00 120.00   67
 66  \w     79.00 126.00   1.00    1.00    --   95.80 -82.00   0.00   47
 67  \w     63.00 183.00   1.00    1.00    --   95.80  82.00 160.27  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1362294000
_diffrn_orient_matrix_UB_12      0.0238668000
_diffrn_orient_matrix_UB_13      -0.0552716000
_diffrn_orient_matrix_UB_21      -0.0493223000
_diffrn_orient_matrix_UB_22      -0.1161824000
_diffrn_orient_matrix_UB_23      -0.0372863000
_diffrn_orient_matrix_UB_31      -0.1304696000
_diffrn_orient_matrix_UB_32      0.0690094000
_diffrn_orient_matrix_UB_33      -0.0436633000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41359
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.538
_diffrn_reflns_theta_min         4.555
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_coef       0.0070(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0392P)^2^+0.2686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3405
_reflns_number_total             3463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc04407e2.cif
_cod_data_source_block           exp_741
_cod_depositor_comments
'Adding full bibliography for 7242297--7242298.cif.'
_cod_database_code               7242298
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.801
_shelx_estimated_absorpt_t_min   0.751
_reflns_odcompleteness_completeness 99.94
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              95180
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.179
_oxdiff_exptl_absorpt_empirical_full_min 0.310