A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C-C bond cleavage using molecular oxygen.
Lim, Bumhee; Park, Seunggun; Park, Jae Hyun; Gam, Jongsik; Kim, Sanghee; Yang, Jung Woon; Lee, Jeeyeon; Organic & biomolecular chemistry 16 (2018) 2105–2113; doi:10.1039/c7ob03188b

data_7156134
_publ_section_title
;
 A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via
 oxidative C-C bond cleavage using molecular oxygen.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2105
_journal_page_last               2113
_journal_paper_doi               10.1039/c7ob03188b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C11 H8 Cl N3 O2'
_chemical_formula_sum            'C11 H8 Cl N3 O2'
_chemical_formula_weight         249.65
_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     dual
_audit_creation_date             2016-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-03-16 deposited with the CCDC.
2018-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.453(3)
_cell_angle_beta                 90.500(2)
_cell_angle_gamma                98.113(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7810(2)
_cell_length_b                   8.5176(3)
_cell_length_c                   11.7466(4)
_cell_measurement_reflns_used    6576
_cell_measurement_temperature    295.6(2)
_cell_measurement_theta_max      76.1210
_cell_measurement_theta_min      5.3610
_cell_volume                     558.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      295.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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   -112.00 -19.00   1.00    1.00    --  -41.49 -57.00 -60.00   93
  2  \w    -67.00  29.00   1.00    1.00    --  -41.49  57.00  90.00   96
  3  \w     53.00  81.00   1.00    1.00    --   41.49 -99.00-150.00   28
  4  \w     13.00 113.00   1.00    1.00    --   41.49  57.00-150.00  100
  5  \w     31.00  61.00   1.00    1.00    --   41.49-125.00-180.00   30
  6  \w     41.00 140.00   1.00    1.00    --  112.00 -61.00  60.00   99
  7  \w     88.00 171.00   1.00    1.00    --  112.00  30.00 -90.00   83
  8  \w    108.00 156.00   1.00    1.00    --  112.00  61.00 -60.00   48
  9  \w     36.00 114.00   1.00    1.00    --  112.00-111.00-120.00   78
 10  \w     94.00 173.00   1.00    1.00    --  112.00  45.00-180.00   79
 11  \w     36.00 129.00   1.00    1.00    --  112.00 -30.00 -30.00   93
 12  \w     54.00  81.00   1.00    1.00    --  112.00 -94.00  30.00   27
 13  \w     52.00 104.00   1.00    1.00    --  112.00 -94.00  60.00   52
 14  \w     60.00 102.00   1.00    1.00    --  112.00 -94.00 -90.00   42
 15  \w     37.00  91.00   1.00    1.00    --  112.00-111.00   0.00   54
 16  \w     81.00 108.00   1.00    1.00    --  112.00 -94.00 150.00   27
 17  \w     45.00 137.00   1.00    1.00    --  112.00 -45.00-150.00   92
 18  \w     36.00 107.00   1.00    1.00    --  112.00-111.00  30.00   71
 19  \w     87.00 116.00   1.00    1.00    --  112.00  45.00 150.00   29
 20  \w    118.00 146.00   1.00    1.00    --  112.00  45.00 150.00   28
 21  \w     89.00 116.00   1.00    1.00    --  112.00-111.00 -60.00   27
 22  \w     90.00 116.00   1.00    1.00    --  112.00-111.00  90.00   26
 23  \w    102.00 159.00   1.00    1.00    --  112.00 111.00   0.00   57
 24  \w    -46.00 -17.00   1.00    1.00    --  -41.49 -38.00  60.00   29
 25  \w    -81.00 -49.00   1.00    1.00    --  -41.49 -38.00  60.00   32
 26  \w      7.00  34.00   1.00    1.00    --   41.49 -99.00 150.00   27
 27  \w     50.00  82.00   1.00    1.00    --   41.49 -99.00 150.00   32
 28  \w     30.00  71.00   1.00    1.00    --   41.49-125.00   0.00   41
 29  \w      6.00  31.00   1.00    1.00    --   42.00  89.00-172.84   25
 30  \w     12.00  37.00   1.00    1.00    --   46.00  83.00  -3.43   25
 31  \w     17.00  42.00   1.00    1.00    --   50.00  80.00  98.03   25
 32  \w     16.00  41.00   1.00    1.00    --   50.00  82.00-108.73   25
 33  \w     16.00  41.00   1.00    1.00    --   50.00  82.00  54.26   25
 34  \w     21.00  46.00   1.00    1.00    --   54.00  79.00 140.43   25
 35  \w     28.00  53.00   1.00    1.00    --   58.00  75.00-156.33   25
 36  \w     27.00  62.00   1.00    1.00    --   58.00  75.00 -85.47   35
 37  \w     28.00  55.00   1.00    1.00    --   58.00  76.00 -32.29   27
 38  \w     97.00 128.00   1.00    1.00    --   58.00  76.00 -32.29   31
 39  \w     34.00  65.00   1.00    1.00    --   62.00  76.00 147.08   31
 40  \w     98.00 137.00   1.00    1.00    --   62.00  75.00   9.48   39
 41  \w     33.00  61.00   1.00    1.00    --   62.00  75.00   9.48   28
 42  \w    101.00 128.00   1.00    1.00    --   62.00  76.00 147.08   27
 43  \w     93.00 131.00   1.00    1.00    --   66.00  75.00 104.05   38
 44  \w     40.00  71.00   1.00    1.00    --   66.00  75.00-136.57   31
 45  \w     35.00  60.00   1.00    1.00    --   66.00  75.00 104.05   25
 46  \w     40.00  67.00   1.00    1.00    --   70.00  77.00-159.98   27
 47  \w    111.00 148.00   1.00    1.00    --   74.00  73.00  37.30   37
 48  \w     43.00  86.00   1.00    1.00    --   74.00  73.00  37.30   43
 49  \w    135.00 164.00   1.00    1.00    --  112.00  61.00 -30.00   29
 50  \w     89.00 118.00   1.00    1.00    --  112.00  61.00 -30.00   29
 51  \w     88.00 168.00   1.00    1.00    --  112.00  61.00  90.00   80
 52  \w    148.00 175.00   1.00    1.00    --  112.00  77.00-120.00   27
 53  \w    151.00 176.00   1.00    1.00    --  112.00  61.00 -60.00   25
 54  \w     80.00 107.00   1.00    1.00    --  112.00  77.00-120.00   27
 55  \w     84.00 109.00   1.00    1.00    --  112.00  61.00 -60.00   25
 56  \w     87.00 114.00   1.00    1.00    --  112.00  45.00 -30.00   27
 57  \w     87.00 114.00   1.00    1.00    --  112.00  61.00  30.00   27
 58  \w    141.00 168.00   1.00    1.00    --  112.00  77.00  30.00   27
 59  \w     83.00 110.00   1.00    1.00    --  112.00  77.00  90.00   27
 60  \w     79.00 115.00   1.00    1.00    --  112.00  77.00  30.00   36
 61  \w     80.00 105.00   1.00    1.00    --  112.00  77.00  60.00   25
 62  \w     81.00 107.00   1.00    1.00    --  112.00  77.00   0.00   26
 63  \w     86.00 113.00   1.00    1.00    --  112.00  61.00-120.00   27
 64  \w     79.00 152.00   1.00    1.00    --  112.00  77.00 -30.00   73
 65  \w    108.00 151.00   1.00    1.00    --  112.00  77.00  60.00   43
 66  \w     80.00 108.00   1.00    1.00    --  112.00  77.00 -90.00   28
 67  \w     83.00 110.00   1.00    1.00    --  112.00  61.00-180.00   27
 68  \w     84.00 111.00   1.00    1.00    --  112.00  61.00 -90.00   27
 69  \w     79.00 106.00   1.00    1.00    --  112.00  77.00 120.00   27
 70  \w    138.00 165.00   1.00    1.00    --  112.00  61.00 120.00   27
 71  \w    116.00 143.00   1.00    1.00    --  112.00  77.00-150.00   27
 72  \w     79.00 108.00   1.00    1.00    --  112.00  77.00-150.00   29
 73  \w     84.00 112.00   1.00    1.00    --  112.00  61.00 120.00   28
 74  \w     79.00 120.00   1.00    1.00    --  112.00  77.00-180.00   41
 75  \w     87.00 152.00   1.00    1.00    --  112.00  61.00   0.00   65
 76  \w     83.00 117.00   1.00    1.00    --  112.00  61.00  60.00   34
 77  \w     86.00 113.00   1.00    1.00    --  112.00  61.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2491874000
_diffrn_orient_matrix_UB_12      0.0636503000
_diffrn_orient_matrix_UB_13      0.0528529000
_diffrn_orient_matrix_UB_21      -0.0386996000
_diffrn_orient_matrix_UB_22      -0.1126330000
_diffrn_orient_matrix_UB_23      0.0867323000
_diffrn_orient_matrix_UB_31      0.0947943000
_diffrn_orient_matrix_UB_32      -0.1353623000
_diffrn_orient_matrix_UB_33      -0.0880502000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.404
_diffrn_reflns_theta_min         3.857
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
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    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0560P)^2^+0.1065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2171
_reflns_number_total             2339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03188b2.cif
_cod_data_source_block           exp_454
_cod_depositor_comments
'Adding full bibliography for 7156133--7156134.cif.'
_cod_database_code               7156134
_chemical_oxdiff_formula         C11H8Cl1N3O2
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-21
_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.811