I2/CHP Mediated [1+1+1+1] Cyclization of Aromaticisocyanide with Amine to Construct 1,3-Diazetidine-2,4-diimine Derivatives
Liu, Haifeng; Zhu, Tong-Hao; Xu, Pei; Wang, Shun-Yi; Ji, Shun-Jun; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02255G

data_7155916
_publ_section_title
;
 I2/CHP Mediated [1+1+1+1] Cyclization of Aromaticisocyanide with Amine to
 Construct 1,3-Diazetidine-2,4-diimine Derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02255G
_journal_year                    2017
_chemical_formula_moiety         'C22 H26 N6 O4'
_chemical_formula_sum            'C22 H26 N6 O4'
_chemical_formula_weight         438.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13mqp4
_audit_creation_date             2014-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-10-31 deposited with the CCDC.
2017-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                82.403(5)
_cell_angle_beta                 77.878(5)
_cell_angle_gamma                69.245(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3830(6)
_cell_length_b                   11.5671(8)
_cell_length_c                   11.8220(8)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    295.25(11)
_cell_measurement_theta_max      24.0370
_cell_measurement_theta_min      3.4630
_cell_volume                     1170.72(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.25(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -18.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   77.0000   90.0000 106

  2 omega   -3.00   92.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   77.0000  -60.0000 95

  3 omega   36.00   74.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   77.0000 -180.0000 38

  4 omega  -48.00   60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327   77.0000 -180.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0242782000
_diffrn_orient_matrix_UB_12      0.0332589000
_diffrn_orient_matrix_UB_13      -0.0507135000
_diffrn_orient_matrix_UB_21      -0.0190688000
_diffrn_orient_matrix_UB_22      -0.0362185000
_diffrn_orient_matrix_UB_23      -0.0345236000
_diffrn_orient_matrix_UB_31      -0.0760991000
_diffrn_orient_matrix_UB_32      0.0435836000
_diffrn_orient_matrix_UB_33      0.0041507000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9733
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     208
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0681
_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^)+(0.1044P)^2^+0.1081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.2235
_reflns_number_gt                2482
_reflns_number_total             4785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02255g2.cif
_cod_data_source_block           g140926c
_cod_original_cell_volume        1170.72(13)
_cod_database_code               7155916
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C16 = C16-C17 = C17-C18
 1.5 with sigma of 0.02
 C15A-C16A = C16A-C17A = C17A-C18A
 1.5 with sigma of 0.02
 C19-C20 = C20-C21 = C21-C22
 1.5 with sigma of 0.02
 C19A-C20A = C20A-C21A = C21A-C22A
 1.5 with sigma of 0.02
3. Rigid bond restraints
 C15, C16, C17, C18, C15A, C16A, C17A, C18A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C15A \\sim C16A \\sim C17A \\sim C18A:
within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C19A \\sim C20A \\sim C21A \\sim C22A:
within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C19A \\sim C20A \\sim C21A \\sim C22A:
within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=
 Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C15A(H15C,H15D), C16A(H16C,
 H16D), C17A(H17C,H17D), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C19A(H19C,H19D), C20A(H20C,H20D), C21A(H21C,H21D)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C22(H22A,H22B,H22C), C22A(H22D,
 H22E,H22F)
;
_olex2_submission_special_instructions 'No special instructions were received'