Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: A Step toward Sustainable Generation of 2,3-Dihydro-1,2,4-oxadiazoles.
Melekhova, Anna A.; Smirnov, Andrey S.; Novikov, Alexander S.; Panikorovskii, Taras L.; Bokach, Nadezhda A.; Kukushkin, Vadim Yu; ACS omega 2 (2017) 1380–1391; doi:10.1021/acsomega.7b00130

data_4516851
_publ_section_title
;
 Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to
 Dialkylcyanamides: A Step toward Sustainable Generation of
 2,3-Dihydro-1,2,4-oxadiazoles.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              1380
_journal_page_last               1391
_journal_paper_doi               10.1021/acsomega.7b00130
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.083(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1035(6)
_cell_length_b                   7.5373(3)
_cell_length_c                   24.9505(14)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4330
_cell_measurement_theta_min      3.6090
_cell_volume                     2225.75(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega -109.00  -74.00   1.0000   16.5800
omega____ theta____ kappa____ phi______ frames
    -      -41.4354 -137.0000    8.0000 35

  2 omega -113.00  -13.00   1.0000   16.5800
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000 -120.0000 100

  3 omega -129.00  -39.00   1.0000   16.5800
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  178.0000  -30.0000 90

  4 omega   71.00   97.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

  5 omega   59.00   95.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 36

  6 omega   31.00   93.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 62

  7 omega   52.00   90.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 38

  8 omega   50.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 46

  9 omega   74.00  177.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -90.0000 103

 10 omega   64.00   90.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -98.0000 -103.0000 26

 11 omega   41.00   94.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 53

 12 omega   39.00   66.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 27

 13 omega   37.00   79.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 42

 14 omega   46.00   71.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 25

 15 omega   30.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  150.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0048157000
_diffrn_orient_matrix_UB_12      -0.1237073000
_diffrn_orient_matrix_UB_13      0.0486341000
_diffrn_orient_matrix_UB_21      0.0513083000
_diffrn_orient_matrix_UB_22      0.1476090000
_diffrn_orient_matrix_UB_23      0.0402809000
_diffrn_orient_matrix_UB_31      -0.1195134000
_diffrn_orient_matrix_UB_32      0.0683470000
_diffrn_orient_matrix_UB_33      0.0009542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.951
_diffrn_reflns_theta_min         3.623
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0497P)^2^+1.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1841
_reflns_number_total             2288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b00130_si_006.cif
_cod_data_source_block           m-146
_cod_original_cell_volume        2225.74(19)
_cod_database_code               4516851
_chemical_oxdiff_formula         'Cu C15 N3 O5'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C8(H8), C13(H13), C12(H12), C11(H11), C4(H4), C7(H7),
 C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'