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_1553201
_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         'C13 H19 N O5'
_chemical_formula_sum            'C13 H19 N O5'
_chemical_formula_weight         269.29
_chemical_name_common            9
_chemical_name_systematic
()-(1S,11R,12S,14S)-11-Hydroxy-10,10-dimethyl-7,13,15-trioxa-8-azatetracyclo[9.3.1.01,8.012,14]pentadecan-9-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-17
_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                 107.6889(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9816(5)
_cell_length_b                   9.2222(4)
_cell_length_c                   13.0751(6)
_cell_measurement_reflns_used    4747
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.75
_cell_volume                     1261.57(10)
_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      100.15
_diffrn_measured_fraction_theta_full 1.000
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21450
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.128
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0589 before and 0.0477 after correction.'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.053
_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     175
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1017P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2275
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00315f2.cif
_cod_data_source_block           aa006_0m
_cod_database_code               1553201
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.973
_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, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C4(H4), C5(H5) 
2.b Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B) 
2.c Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O4(H4A) 
;