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_4516852
_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         'C28 H26 N3 O'
_chemical_formula_sum            'C28 H26 N3 O'
_chemical_formula_weight         420.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-26
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.8249(4)
_cell_length_b                   8.55531(17)
_cell_length_c                   24.3304(5)
_cell_measurement_reflns_used    9380
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0740
_cell_measurement_theta_min      4.2290
_cell_volume                     4334.79(15)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_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 0.9719
_diffrn_measured_fraction_theta_max 0.9719
_diffrn_measurement_details
;
  1 omega  -28.00   32.00   1.0000    1.9950
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000 -120.0000 60

  2 omega    2.00   27.00   1.0000    1.9950
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000 -180.0000 25

  3 omega   83.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 26

  4 omega   93.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 28

  5 omega   66.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 26

  6 omega   55.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 35

  7 omega   36.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 54

  8 omega   36.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 57

  9 omega   41.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 45

 10 omega   53.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 31

 11 omega   45.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 64

 12 omega   41.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 43

 13 omega   37.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 41

 14 omega   87.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 35

 15 omega  140.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  150.0000 28

 16 omega   99.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  117.0000  -37.0000 26

 17 omega  148.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  117.0000  -37.0000 28

 18 omega   97.00  130.00   1.0000    1.9950
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -30.0000 33

 19 omega   94.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -90.0000 43

 20 omega   36.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 40

 21 omega  -67.00  -38.00   1.0000    1.9950
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  178.0000    0.0000 29

 22 omega -116.00  -90.00   1.0000    1.9950
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  178.0000    0.0000 26
;
_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      -0.0496432000
_diffrn_orient_matrix_UB_12      -0.1306809000
_diffrn_orient_matrix_UB_13      0.0097143000
_diffrn_orient_matrix_UB_21      -0.0159465000
_diffrn_orient_matrix_UB_22      -0.0010501000
_diffrn_orient_matrix_UB_23      -0.0618299000
_diffrn_orient_matrix_UB_31      0.0524561000
_diffrn_orient_matrix_UB_32      -0.1239235000
_diffrn_orient_matrix_UB_33      -0.0096068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19862
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.21
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83006
_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            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                3517
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00130_si_004.cif
_cod_data_source_block           sas-761
_cod_original_cell_volume        4334.79(14)
_cod_database_code               4516852
_chemical_oxdiff_formula         'C18 H36 N2'
_reflns_odcompleteness_completeness 97.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59