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_4516848
_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         'C30 H27 N3 O'
_chemical_formula_sum            'C30 H27 N3 O'
_chemical_formula_weight         445.55
_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     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                 95.972(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.43120(13)
_cell_length_b                   22.8417(5)
_cell_length_c                   15.8232(3)
_cell_measurement_reflns_used    13412
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1680
_cell_measurement_theta_min      3.3740
_cell_volume                     2311.81(8)
_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 0.9960
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_details
;
  1 omega   -5.00   21.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000   90.0000 26

  2 omega  -62.00   32.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   57.0000  -30.0000 94

  3 omega  -49.00   31.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -90.0000 80

  4 omega   33.00   78.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000   60.0000 45

  5 omega   78.00  121.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 43

  6 omega  118.00  144.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 26

  7 omega   85.00  120.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   60.0000 35

  8 omega   74.00  121.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 47

  9 omega  120.00  145.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 25

 10 omega   92.00  127.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  150.0000 35

 11 omega   77.00  102.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 25

 12 omega   77.00  103.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 26

 13 omega   64.00  105.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 41

 14 omega   51.00   93.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 42

 15 omega   81.00  120.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -120.0000 39

 16 omega   91.00  118.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 27

 17 omega   84.00  109.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 25

 18 omega   79.00  104.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -150.0000 25

 19 omega   52.00   77.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 25

 20 omega   42.00   71.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 29

 21 omega   44.00  105.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 61

 22 omega   56.00  106.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 50

 23 omega  100.00  178.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 78

 24 omega  109.00  135.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 26

 25 omega   97.00  128.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 31

 26 omega   91.00  144.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 53

 27 omega  128.00  168.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   90.0000 40

 28 omega   95.00  167.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000    0.0000 72

 29 omega  117.00  143.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 26

 30 omega  116.00  178.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 62

 31 omega   96.00  134.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -120.0000 38

 32 omega   64.00   89.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 25

 33 omega   44.00   81.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 37

 34 omega   60.00   94.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  143.8284 34

 35 omega   56.00   81.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 25

 36 omega   57.00   83.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  150.0000 26

 37 omega   49.00   75.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 26

 38 omega   46.00   73.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 27

 39 omega   40.00   97.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 57

 40 omega   53.00   97.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000    0.0000 44

 41 omega   39.00   89.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 50

 42 omega   72.00  164.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -150.0000 92

 43 omega   41.00   72.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000  -90.0000 31

 44 omega   31.00   86.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -30.0000 55

 45 omega   46.00   71.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 25

 46 omega   41.00   67.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 26

 47 omega   13.00   92.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -       41.4354   57.0000 -150.0000 79

 48 omega   39.00   65.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -150.0000 26

 49 omega   40.00   91.00   1.0000   10.6600
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 51

 50 omega -115.00  -22.00   1.0000    2.6650
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000  -90.0000 93
;
_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      -0.2156278000
_diffrn_orient_matrix_UB_12      -0.0202983000
_diffrn_orient_matrix_UB_13      0.0227541000
_diffrn_orient_matrix_UB_21      0.0613884000
_diffrn_orient_matrix_UB_22      -0.0641185000
_diffrn_orient_matrix_UB_23      -0.0147790000
_diffrn_orient_matrix_UB_31      0.0879970000
_diffrn_orient_matrix_UB_32      -0.0051327000
_diffrn_orient_matrix_UB_33      0.0940560000
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29518
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83291
_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    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0668P)^2^+0.6057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                4209
_reflns_number_total             4577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00130_si_003.cif
_cod_data_source_block           sas_763
_cod_original_cell_volume        2311.80(8)
_cod_database_code               4516848
_chemical_oxdiff_formula         'C10 N4'
_reflns_odcompleteness_completeness 94.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95