Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates
Acharya, A.; Eickhoff, J. A.; Chen, K.; Catalano, V. J.; Jeffrey, C. S.; Organic Chemistry Frontiers 3 (2016) 330–; doi:10.1039/C5QO00315F

data_1553200
_publ_section_title
;
 Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3)
 cyloaddition reactions of aza-oxyallylic cation intermediates
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              330
_journal_paper_doi               10.1039/C5QO00315F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C15 H21 N O4'
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.32
_chemical_name_common            12
_chemical_name_systematic
; 
12-Acetyl-2,2-Dimethyl-5.14-dioxa-4-azabicyclo[9.2.1]tetradeca-1(13),11-dien-3-one 
;
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-16
_audit_creation_method
; 
Olex2 1.2 
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) 
;
_audit_update_record
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0774(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0197(5)
_cell_length_b                   16.2710(5)
_cell_length_c                   10.1414(3)
_cell_measurement_reflns_used    8941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.39
_cell_volume                     2773.26(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            41363
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.742
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0573 before and 0.0533 after correction.'
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0987P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4309
_reflns_number_total             5170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00315f2.cif
_cod_data_source_block           aa005_0ma
_cod_depositor_comments
;

2022-03-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H42 N2 O8'
_cod_original_formula_weight         558.65
_cod_original_formula_moiety         '2(C15 H21 N O4)'
_cod_original_formula_units_Z            4
_cod_database_code               1553200
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.976
_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.a Secondary CH2 refined with riding coordinates: 
 C7(H7a,H7b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), 
 C22(H22a,H22b), C23(H23a,H23b), C24(H24a,H24b), C25(H25a,H25b), C26(H26a,H26b) 
2.b Aromatic/amide H refined with riding coordinates: 
 C4(H4), C19(H19) 
2.c Idealised Me refined as rotating group: 
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c), C27(H27a,H27b, 
 H27c), C28(H28a,H28b,H28c), C30(H30a,H30b,H30c) 
;