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_1553197
_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 H24 Br N O5'
_chemical_formula_sum            'C15 H24 Br N O5'
_chemical_formula_weight         378.26
_chemical_name_common            20
_chemical_name_systematic
()-(1S,11S,13R,14R,Z)-14-Bromo-11,13-dimethoxy-15,15-dimethyl-2.5.12-trioxa-4-azatricyclo[9.2.1.13,13]pentadec-3-ene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2013-12-06
_audit_creation_method
; 
  Olex2 1.2 
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466) 
;
_audit_update_record
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                116.0658(15)
_cell_angle_beta                 107.1142(16)
_cell_angle_gamma                90.5266(17)
_cell_formula_units_Z            2
_cell_length_a                   8.8508(8)
_cell_length_b                   10.0352(8)
_cell_length_c                   10.7879(9)
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.23
_cell_volume                     811.83(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_structure_refinement
; 
XL, G.M. Sheldrick, Acta Cryst. 
(2008). A64, 112-122 
;
_computing_structure_solution
; 
XS, G.M. Sheldrick, Acta Cryst. 
(2008). A64, 112-122 
;
_diffrn_ambient_temperature      99.65
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.228
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0847 before and 0.0638 after correction. 
The Ratio of minimum to maximum transmission is 0.8637. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0287P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2538
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00315f2.cif
_cod_data_source_block           aa001_0m
_cod_database_code               1553197
_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 Ternary CH refined with riding coordinates: 
 C5(H5), C4(H4) 
2.b Secondary CH2 refined with riding coordinates: 
 C7(H7a,H7b), C8(H8a,H8b), C11(H11a,H11b), C9(H9a,H9b), C10(H10a,H10b) 
2.c Idealised Me refined as rotating group: 
 C15(H15a,H15b,H15c), C14(H14a,H14b,H14c), C12(H12a,H12b,H12c), C13(H13a,H13b, 
 H13c) 
;
_shelx_estimated_absorpt_t_max   0.818
_shelx_estimated_absorpt_t_min   0.713
_shelx_hkl_checksum              17574