DABCO-Mediated [3 + 3] Cycloaddition of Azomethine Imines with in Situ Generated Nitrile Oxides from Hydroximoyl Chlorides
Fang, Qing-Yun; Jin, Hai-shan; Wang, Ru-Bing; Zhao, Li-Ming; Chemical Communications  (2019) –; doi:10.1039/C9CC05367K

data_7123973
_publ_section_title
;
 DABCO-Mediated [3 + 3] Cycloaddition of Azomethine Imines with in Situ
 Generated Nitrile Oxides from Hydroximoyl Chlorides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05367K
_journal_year                    2019
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.    2019-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2898(13)
_cell_length_b                   11.4074(13)
_cell_length_c                   22.636(3)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8620
_cell_measurement_theta_min      4.3310
_cell_volume                     3173.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00  88.00   1.00   10.00    --   15.49 178.00  60.00   52
  2  \w    -66.00  -1.00   1.00   10.00    --  -16.28 -57.00 120.00   65
  3  \w    -76.00 -33.00   1.00   10.00    --  -16.28 -38.00-180.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206257000
_diffrn_orient_matrix_UB_12      -0.0492605000
_diffrn_orient_matrix_UB_13      0.0154327000
_diffrn_orient_matrix_UB_21      0.0064299000
_diffrn_orient_matrix_UB_22      -0.0348917000
_diffrn_orient_matrix_UB_23      -0.0257246000
_diffrn_orient_matrix_UB_31      0.0535409000
_diffrn_orient_matrix_UB_32      -0.0148183000
_diffrn_orient_matrix_UB_33      0.0090413000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.1300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9906
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.572
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0106P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1570
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05367k2.cif
_cod_data_source_block           exp_7111
_cod_original_cell_volume        3173.5(6)
_cod_database_code               7123973
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.59
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.007 and sigma for
terminal atoms of 0.014
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6), C14(H14), C12(H12), C13(H13), C10(H10),
 C11(H11)
;
_shelx_res_checksum              8897
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 10.235
_oxdiff_exptl_absorpt_empirical_full_min 0.431