Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides.
Bhat, Shreesha V.; Robinson, David; Moses, John E.; Sharma, Pallavi; Organic letters 18 (2016) 1100–; doi:10.1021/acs.orglett.6b00203

data_1542715
_publ_section_title
;
 Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ
 Generated Cyanamide Ions and Nitrile Oxides.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1100
_journal_paper_doi               10.1021/acs.orglett.6b00203
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-20
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_c                   12.9247(11)
_cell_measurement_reflns_used    4065
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.0510
_cell_measurement_theta_min      3.4980
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      'N2 gas'
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_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3613
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_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega  -22.00   32.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -90.0000 27

  2 omega   26.00   54.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152   57.0000  120.0000 14

  3 omega   84.00  122.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000  120.0000 19

  4 omega  122.00  150.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000   90.0000 14

  5 omega   91.00  127.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  150.0000 18

  6 omega   82.00  116.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000   90.0000 17

  7 omega   85.00  131.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000   90.0000 23

  8 omega   88.00  178.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   52.0000  -14.0000 45

  9 omega  141.00  169.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  -90.0000 14

 10 omega   90.00  172.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  -60.0000 41

 11 omega   83.00  111.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000   60.0000 14

 12 omega   77.00  103.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   60.0000 13

 13 omega   77.00  125.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   30.0000 24

 14 omega   81.00  135.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   61.0000   60.0000 27

 15 omega   83.00  127.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   45.0000  150.0000 22

 16 omega   76.00  102.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   77.0000   90.0000 13

 17 omega   39.00   91.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000    0.0000 26

 18 omega   70.00   98.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -45.0000   30.0000 14

 19 omega   40.00  106.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -61.0000    0.0000 33

 20 omega   84.00  126.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822   30.0000  -90.0000 21

 21 omega   37.00   91.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -45.0000 -120.0000 27

 22 omega   33.00   87.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -30.0000 -180.0000 27

 23 omega   36.00   78.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152 -125.0000 -180.0000 21

 24 omega   36.00   74.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.3822  -45.0000  120.0000 19

 25 omega -108.00  -22.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000   90.0000 43

 26 omega -118.00   40.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000    0.0000 -120.0000 79
;
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_diffrn_orient_matrix_UB_11      0.0112402000
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_diffrn_orient_matrix_UB_21      0.0806877000
_diffrn_orient_matrix_UB_22      0.1636464000
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_diffrn_orient_matrix_UB_31      -0.0645514000
_diffrn_orient_matrix_UB_32      0.2026291000
_diffrn_orient_matrix_UB_33      -0.0051131000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_min       -18
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.991
_diffrn_reflns_theta_min         5.972
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.784
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.6815
_exptl_crystal_size_mid          0.5067
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.4480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            ol6b00203_si_002.cif
_cod_data_source_block           pasjmb
_cod_original_cell_volume        1131.86(16)
_cod_database_code               1542715
_nottingham_internal_coll_name   PASJMB
_nottingham_internal_coll_number 14075
_nottingham_internal_coll_client PAS/JEM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time 2.0000
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   17/10/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user pczalg
_nottingham_internal_process_date 13/11/2014
_nottingham_internal_solution_user pczalg
_nottingham_internal_solution_date 13/11/2014
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_nottingham_internal_refinement_date 13/11/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_validation_date 28/11/2014
_nottingham_internal_archive_date 28/11/2014
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C14 H10 N2 O2'
_chemical_oxdiff_usercomment
'PASJMB #14075 SN-324 IN FOMBLIN FILM ON A MICROMOUNT FOR PAS/JEM'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_shelx_res_checksum              54254
_shelx_hkl_checksum              48570
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_special_instructions 'No special instructions were received'