Synthesis of α-aminooxy amides through [3 + 3] cycloaddition and Sc(OTf)<sub>3</sub>-catalyzed double C-N bond cleavage in a one-pot reaction.
Luo, Yan; Chen, Chun-Hua; Zhu, Fan; Mo, Dong-Liang; Organic & biomolecular chemistry 18 (2020) 8209–8218; doi:10.1039/d0ob01788d

data_7157719
_publ_section_title
;
 Synthesis of \a-aminooxy amides through [3 + 3] cycloaddition and
 Sc(OTf)<sub>3</sub>-catalyzed double C-N bond cleavage in a one-pot
 reaction.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8209
_journal_page_last               8218
_journal_paper_doi               10.1039/d0ob01788d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-04 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.014(2)
_cell_length_b                   10.0228(11)
_cell_length_c                   21.573(5)
_cell_measurement_reflns_used    1041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1890
_cell_measurement_theta_min      3.8650
_cell_volume                     3246.4(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -12.00  57.00   1.00   10.00    --   17.61  77.00 150.00   69
  2  \w    -86.00  23.00   1.00   10.00    --  -19.80 -19.00   0.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0192021000
_diffrn_orient_matrix_UB_12      0.0030643000
_diffrn_orient_matrix_UB_13      -0.0300338000
_diffrn_orient_matrix_UB_21      -0.0419370000
_diffrn_orient_matrix_UB_22      0.0181526000
_diffrn_orient_matrix_UB_23      -0.0125614000
_diffrn_orient_matrix_UB_31      0.0103373000
_diffrn_orient_matrix_UB_32      0.0682769000
_diffrn_orient_matrix_UB_33      0.0046471000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11068
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_min         3.306
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1274
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.2084
_refine_ls_R_factor_gt           0.0871
_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^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2286
_refine_ls_wR_factor_ref         0.3103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1287
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01788d2.cif
_cod_data_source_block           20181222_mdl_zhp_ch9_67
_cod_depositor_comments
;
Adding full bibliography for 7157719--7157720.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.57(C18 H18 N2 O3)'
_cod_original_formula_units_Z            14
_cod_original_cell_volume        3246.5(9)
_cod_database_code               7157719
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.60
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C6(H6), C3(H3), C10(H10), C9(H9), C4(H4), C5(H5), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              66000
_shelx_hkl_checksum              81739
_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 1.808
_oxdiff_exptl_absorpt_empirical_full_min 0.408