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_4516850
_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         'C56 H52 Cu N4 O4, 2(B F4)'
_chemical_formula_sum            'C56 H52 B2 Cu F8 N4 O4'
_chemical_formula_weight         1082.18
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-27
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.668(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8731(5)
_cell_length_b                   13.9085(4)
_cell_length_c                   21.1754(6)
_cell_measurement_reflns_used    9815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.4823
_cell_measurement_theta_min      2.6452
_cell_volume                     4959.3(2)
_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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
  1 omega  -92.00  -41.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2749 -178.0000  -90.0000 51

  2 omega  -85.00  -51.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2749 -178.0000 -150.0000 34

  3 omega  -33.00   43.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686  -57.0000 -150.0000 76

  4 omega  -25.00   73.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686  -19.0000   90.0000 98

  5 omega   57.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686   57.0000  120.0000 36

  6 omega   10.00   42.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686   57.0000  -60.0000 32

  7 omega   58.00   95.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686   57.0000  -60.0000 37

  8 omega  -15.00  101.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686   19.0000 -120.0000 116

  9 omega   14.00   50.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3686  -77.0000    0.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0343376000
_diffrn_orient_matrix_UB_12      0.0292636000
_diffrn_orient_matrix_UB_13      -0.0008463000
_diffrn_orient_matrix_UB_21      0.0164759000
_diffrn_orient_matrix_UB_22      -0.0227254000
_diffrn_orient_matrix_UB_23      0.0278022000
_diffrn_orient_matrix_UB_31      0.0180236000
_diffrn_orient_matrix_UB_32      -0.0350263000
_diffrn_orient_matrix_UB_33      -0.0187831000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24511
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.65
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87619
_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            blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2236
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0297
_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          0.1127
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                5241
_reflns_number_total             5691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00130_si_005.cif
_cod_data_source_block           m49
_cod_original_cell_volume        4959.2(2)
_cod_database_code               4516850
_chemical_oxdiff_formula         'C34 H32 N8 O8 Cu1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44