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_4516849
_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         'C19 H21 N3 O'
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 96.586(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5573(16)
_cell_length_b                   8.6999(9)
_cell_length_c                   12.7827(14)
_cell_measurement_reflns_used    3163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2760
_cell_measurement_theta_min      2.7268
_cell_volume                     1608.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_details
;
  1 omega  -65.00  -38.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031 -178.0000 -120.0000 27

  2 omega  -97.00  -70.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031  178.0000   30.0000 27

  3 omega  -62.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031   19.0000  150.0000 111

  4 omega   35.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3406  178.0000  -30.0000 62

  5 omega  -91.00   10.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031  -77.0000  120.0000 101

  6 omega  -93.00  -18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031  -38.0000  -30.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0371863000
_diffrn_orient_matrix_UB_12      0.0433885000
_diffrn_orient_matrix_UB_13      0.0217546000
_diffrn_orient_matrix_UB_21      0.0032419000
_diffrn_orient_matrix_UB_22      -0.0539654000
_diffrn_orient_matrix_UB_23      0.0367553000
_diffrn_orient_matrix_UB_31      0.0414633000
_diffrn_orient_matrix_UB_32      0.0430843000
_diffrn_orient_matrix_UB_33      0.0242045000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12789
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+1.6306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                2938
_reflns_number_total             3683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00130_si_002.cif
_cod_data_source_block           m_220_new2
_cod_database_code               4516849
_chemical_oxdiff_formula         'C12 N2 H12'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50