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_7156133
_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         'C19 H13 Cl F3 N3 O2'
_chemical_formula_sum            'C19 H13 Cl F3 N3 O2'
_chemical_formula_weight         407.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-04-19 deposited with the CCDC.
2018-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1816(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.77529(12)
_cell_length_b                   22.1018(5)
_cell_length_c                   14.0999(3)
_cell_measurement_reflns_used    13662
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      74.9640
_cell_measurement_theta_min      3.7490
_cell_volume                     1765.61(7)
_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      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_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    -66.00  33.00   1.00    3.73    --  -41.24  38.00 150.00   99
  2  \w      1.00  82.00   1.00    3.73    --   41.24 -99.00 -90.00   81
  3  \w      9.00 117.00   1.00    3.73    --   41.24  77.00   0.00  108
  4  \w     36.00 145.00   1.00   12.35    --  112.00 -77.00  90.00  109
  5  \w     57.00 151.00   1.00   12.35    --  112.00 178.00-120.00   94
  6  \w    100.00 178.00   1.00   12.35    --  112.00 111.00-180.00   78
  7  \w     83.00 178.00   1.00   12.35    --  112.00  61.00-120.00   95
  8  \w    100.00 178.00   1.00   12.35    --  112.00 111.00  60.00   78
  9  \w     17.00  72.00   1.00    3.73    --   41.24  38.00-180.00   55
 10  \w     24.00  50.00   1.00    5.92    --   41.49-125.00  60.00   26
 11  \w     52.00  78.00   1.00    5.92    --   41.49 -99.00 150.00   26
 12  \w     88.00 113.00   1.00   12.39    --  112.00-104.00  70.00   25
 13  \w    106.00 148.00   1.00   12.39    --  112.00  45.00-180.00   42
 14  \w     83.00 117.00   1.00   12.39    --  112.00 -61.00 -90.00   34
 15  \w   -118.00  -9.00   1.00    5.92    --  -41.49 -77.00-150.00  109
 16  \w    -70.00  21.00   1.00    5.92    --  -41.49  57.00-180.00   91
 17  \w   -115.00 -13.00   1.00    5.92    --  -41.49 -57.00  60.00  102
 18  \w     13.00 115.00   1.00    5.92    --   41.49  57.00 -60.00  102
 19  \w    -31.00  70.00   1.00    5.92    --   41.49 -57.00 -30.00  101
 20  \w   -118.00  -9.00   1.00    6.62    --  -41.49 -77.00 120.00  109
 21  \w     13.00 115.00   1.00    6.62    --   41.49  57.00-150.00  102
 22  \w     17.00  98.00   1.00    6.62    --   41.49  38.00  60.00   81
 23  \w      9.00 118.00   1.00    6.62    --   41.49  77.00  90.00  109
 24  \w      9.00 118.00   1.00    6.46    --   41.49  77.00  30.00  109
 25  \w      9.00 118.00   1.00    6.46    --   41.49  77.00-180.00  109
 26  \w      9.00  97.00   1.00    6.46    --   41.49  77.00  60.00   88
 27  \w     13.00 115.00   1.00    6.46    --   41.49  57.00   0.00  102
 28  \w     17.00 116.00   1.00    6.46    --   41.49  38.00-180.00   99
 29  \w     17.00 116.00   1.00    6.46    --   41.49  38.00   0.00   99
 30  \w    -35.00  71.00   1.00    6.46    --   41.49 -77.00 -60.00  106
 31  \w      9.00 118.00   1.00    6.46    --   41.49  77.00 120.00  109
;
_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      0.2165191000
_diffrn_orient_matrix_UB_12      0.0346844000
_diffrn_orient_matrix_UB_13      -0.0205510000
_diffrn_orient_matrix_UB_21      0.0836585000
_diffrn_orient_matrix_UB_22      -0.0574194000
_diffrn_orient_matrix_UB_23      -0.0452950000
_diffrn_orient_matrix_UB_31      -0.1415740000
_diffrn_orient_matrix_UB_32      0.0189720000
_diffrn_orient_matrix_UB_33      -0.0996394000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.696
_diffrn_reflns_theta_min         3.770
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68775
_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    1.534
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0350P)^2^+2.0471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3306
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03188b2.cif
_cod_data_source_block           exp_447
_cod_depositor_comments
'Adding full bibliography for 7156133--7156134.cif.'
_cod_original_cell_volume        1765.61(6)
_cod_database_code               7156133
_chemical_oxdiff_formula         ' C19H13Cl1F3N3O2'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F0)=Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(F003)=Sof(F006)=Sof(F009)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00G(H00G)
3.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B), C00S(H00C,H00E)
3.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-23
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.500