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#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/31/1553197.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1553197
loop_
_publ_author_name
'Acharya, A.'
'Eickhoff, J. A.'
'Chen, K.'
'Catalano, V. J.'
'Jeffrey, C. S.'
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0287P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.74209(4) 0.65046(4) 0.80397(3) 0.01777(11) Uani 1 1 d . .
O5 O 1.0140(2) 0.7475(2) 1.0595(2) 0.0175(5) Uani 1 1 d . .
C5 C 0.7326(3) 0.6611(3) 0.9859(3) 0.0149(7) Uani 1 1 d . .
H5 H 0.6869 0.5600 0.9676 0.018 Uiso 1 1 calc R U
N1 N 0.5810(3) 0.8242(3) 1.3710(3) 0.0170(6) Uani 1 1 d . .
O1 O 0.5437(2) 0.7307(2) 1.1212(2) 0.0130(5) Uani 1 1 d . .
O3 O 0.8755(2) 0.8565(2) 1.2231(2) 0.0144(5) Uani 1 1 d . .
O2 O 0.5176(2) 0.6719(2) 1.3264(2) 0.0172(5) Uani 1 1 d . .
C6 C 0.8971(3) 0.7179(3) 1.1117(3) 0.0137(7) Uani 1 1 d . .
C2 C 0.6616(4) 0.9876(3) 1.2804(3) 0.0147(7) Uani 1 1 d . .
C1 C 0.5876(3) 0.8412(3) 1.2631(3) 0.0134(7) Uani 1 1 d . .
C4 C 0.6261(3) 0.7749(3) 1.0439(3) 0.0130(7) Uani 1 1 d . .
H4 H 0.5510 0.7938 0.9658 0.016 Uiso 1 1 calc R U
C7 C 0.9447(4) 0.6134(3) 1.1806(3) 0.0170(7) Uani 1 1 d . .
H7A H 1.0347 0.6699 1.2733 0.020 Uiso 1 1 calc R U
H7B H 0.9855 0.5294 1.1144 0.020 Uiso 1 1 calc R U
C15 C 1.1736(3) 0.8041(4) 1.1622(3) 0.0232(8) Uani 1 1 d . .
H15A H 1.2406 0.8392 1.1212 0.035 Uiso 1 1 calc R U
H15B H 1.2182 0.7239 1.1825 0.035 Uiso 1 1 calc R U
H15C H 1.1711 0.8879 1.2533 0.035 Uiso 1 1 calc R U
C3 C 0.7441(3) 0.9152(3) 1.1637(3) 0.0125(6) Uani 1 1 d . .
C8 C 0.8145(4) 0.5460(3) 1.2139(3) 0.0186(7) Uani 1 1 d . .
H8A H 0.8022 0.4350 1.1617 0.022 Uiso 1 1 calc R U
H8B H 0.7113 0.5753 1.1758 0.022 Uiso 1 1 calc R U
C11 C 0.5955(4) 0.6382(4) 1.4450(3) 0.0203(7) Uani 1 1 d . .
H11A H 0.5136 0.5896 1.4643 0.024 Uiso 1 1 calc R U
H11B H 0.6487 0.7333 1.5346 0.024 Uiso 1 1 calc R U
C9 C 0.8514(4) 0.5971(4) 1.3787(3) 0.0247(8) Uani 1 1 d . .
H9A H 0.9513 0.5626 1.4156 0.030 Uiso 1 1 calc R U
H9B H 0.8700 0.7083 1.4317 0.030 Uiso 1 1 calc R U
C10 C 0.7173(4) 0.5372(4) 1.4125(4) 0.0262(8) Uani 1 1 d . .
H10A H 0.6616 0.4393 1.3278 0.031 Uiso 1 1 calc R U
H10B H 0.7661 0.5187 1.4975 0.031 Uiso 1 1 calc R U
O4 O 0.7816(2) 1.0006(2) 1.1000(2) 0.0182(5) Uani 1 1 d . .
C14 C 0.9163(4) 1.1178(4) 1.1876(4) 0.0270(8) Uani 1 1 d . .
H14A H 0.9530 1.1476 1.1247 0.040 Uiso 1 1 calc R U
H14B H 1.0030 1.0819 1.2394 0.040 Uiso 1 1 calc R U
H14C H 0.8856 1.2045 1.2588 0.040 Uiso 1 1 calc R U
C12 C 0.5307(4) 1.0691(3) 1.2309(3) 0.0206(7) Uani 1 1 d . .
H12A H 0.4634 1.0031 1.1297 0.031 Uiso 1 1 calc R U
H12B H 0.5800 1.1606 1.2370 0.031 Uiso 1 1 calc R U
H12C H 0.4646 1.0960 1.2944 0.031 Uiso 1 1 calc R U
C13 C 0.7704(4) 1.0887(3) 1.4368(3) 0.0193(7) Uani 1 1 d . .
H13A H 0.7067 1.1179 1.5024 0.029 Uiso 1 1 calc R U
H13B H 0.8212 1.1790 1.4419 0.029 Uiso 1 1 calc R U
H13C H 0.8531 1.0344 1.4666 0.029 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O5 C15 116.3(2)
Br1 C5 H5 109.5
C6 C5 Br1 114.07(19)
C6 C5 H5 109.5
C4 C5 Br1 109.21(19)
C4 C5 H5 109.5
C4 C5 C6 104.9(2)
C1 N1 O2 111.3(2)
C1 O1 C4 108.7(2)
C3 O3 C6 111.2(2)
N1 O2 C11 107.3(2)
O5 C6 C5 108.6(2)
O5 C6 O3 109.8(2)
O5 C6 C7 111.9(2)
O3 C6 C5 104.4(2)
O3 C6 C7 107.4(2)
C7 C6 C5 114.5(2)
C1 C2 C3 96.0(2)
C1 C2 C12 110.2(2)
C1 C2 C13 112.0(2)
C12 C2 C3 110.2(2)
C13 C2 C3 116.9(3)
C13 C2 C12 110.7(2)
N1 C1 O1 125.8(3)
N1 C1 C2 122.5(3)
O1 C1 C2 111.5(2)
C5 C4 H4 112.5
O1 C4 C5 110.5(2)
O1 C4 H4 112.5
O1 C4 C3 104.1(2)
C3 C4 C5 104.0(2)
C3 C4 H4 112.5
C6 C7 H7A 108.0
C6 C7 H7B 108.0
C6 C7 C8 117.3(3)
H7A C7 H7B 107.2
C8 C7 H7A 108.0
C8 C7 H7B 108.0
O5 C15 H15A 109.5
O5 C15 H15B 109.5
O5 C15 H15C 109.5
H15A C15 H15B 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O3 C3 C2 107.3(2)
O3 C3 C4 103.4(2)
C4 C3 C2 104.5(2)
O4 C3 O3 114.1(2)
O4 C3 C2 117.7(2)
O4 C3 C4 108.5(2)
C7 C8 H8A 108.9
C7 C8 H8B 108.9
C7 C8 C9 113.3(3)
H8A C8 H8B 107.7
C9 C8 H8A 108.9
C9 C8 H8B 108.9
O2 C11 H11A 109.1
O2 C11 H11B 109.1
O2 C11 C10 112.6(3)
H11A C11 H11B 107.8
C10 C11 H11A 109.1
C10 C11 H11B 109.1
C8 C9 H9A 108.9
C8 C9 H9B 108.9
H9A C9 H9B 107.7
C10 C9 C8 113.3(3)
C10 C9 H9A 108.9
C10 C9 H9B 108.9
C11 C10 C9 115.1(3)
C11 C10 H10A 108.5
C11 C10 H10B 108.5
C9 C10 H10A 108.5
C9 C10 H10B 108.5
H10A C10 H10B 107.5
C3 O4 C14 116.5(2)
O4 C14 H14A 109.5
O4 C14 H14B 109.5
O4 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C2 C12 H12A 109.5
C2 C12 H12B 109.5
C2 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C2 C13 H13A 109.5
C2 C13 H13B 109.5
C2 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.946(3)
O5 C6 1.400(3)
O5 C15 1.434(3)
C5 H5 1.0000
C5 C6 1.558(4)
C5 C4 1.524(4)
N1 O2 1.436(3)
N1 C1 1.266(4)
O1 C1 1.369(3)
O1 C4 1.449(3)
O3 C6 1.445(3)
O3 C3 1.420(3)
O2 C11 1.445(3)
C6 C7 1.530(4)
C2 C1 1.514(4)
C2 C3 1.546(4)
C2 C12 1.528(4)
C2 C13 1.525(4)
C4 H4 1.0000
C4 C3 1.524(4)
C7 H7A 0.9900
C7 H7B 0.9900
C7 C8 1.535(4)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C3 O4 1.401(3)
C8 H8A 0.9900
C8 H8B 0.9900
C8 C9 1.544(4)
C11 H11A 0.9900
C11 H11B 0.9900
C11 C10 1.498(4)
C9 H9A 0.9900
C9 H9B 0.9900
C9 C10 1.528(4)
C10 H10A 0.9900
C10 H10B 0.9900
O4 C14 1.425(3)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Br1 C5 C6 O5 -0.2(3)
Br1 C5 C6 O3 116.9(2)
Br1 C5 C6 C7 -126.0(2)
Br1 C5 C4 O1 147.85(18)
Br1 C5 C4 C3 -100.9(2)
O5 C6 C7 C8 -167.9(2)
C5 C6 C7 C8 -43.8(4)
C5 C4 C3 O3 -33.5(3)
C5 C4 C3 C2 -145.6(2)
C5 C4 C3 O4 88.1(3)
N1 O2 C11 C10 -106.0(3)
O1 C4 C3 O3 82.4(2)
O1 C4 C3 C2 -29.8(3)
O1 C4 C3 O4 -156.1(2)
O3 C6 C7 C8 71.6(3)
O3 C3 O4 C14 -51.6(3)
O2 N1 C1 O1 -1.1(4)
O2 N1 C1 C2 -175.1(2)
O2 C11 C10 C9 58.2(4)
C6 C5 C4 O1 -89.5(3)
C6 C5 C4 C3 21.7(3)
C6 O3 C3 C2 144.0(2)
C6 O3 C3 C4 33.9(3)
C6 O3 C3 O4 -83.7(3)
C6 C7 C8 C9 -116.3(3)
C2 C3 O4 C14 75.5(3)
C1 N1 O2 C11 146.9(3)
C1 O1 C4 C5 119.4(2)
C1 O1 C4 C3 8.2(3)
C1 C2 C3 O3 -72.4(2)
C1 C2 C3 C4 37.0(3)
C1 C2 C3 O4 157.3(2)
C4 C5 C6 O5 -119.7(2)
C4 C5 C6 O3 -2.6(3)
C4 C5 C6 C7 114.5(3)
C4 O1 C1 N1 -157.0(3)
C4 O1 C1 C2 17.7(3)
C4 C3 O4 C14 -166.3(2)
C7 C8 C9 C10 176.7(3)
C15 O5 C6 C5 178.8(2)
C15 O5 C6 O3 65.2(3)
C15 O5 C6 C7 -53.9(3)
C3 O3 C6 O5 96.4(3)
C3 O3 C6 C5 -19.8(3)
C3 O3 C6 C7 -141.8(2)
C3 C2 C1 N1 140.5(3)
C3 C2 C1 O1 -34.3(3)
C8 C9 C10 C11 -91.9(3)
C12 C2 C1 N1 -105.4(3)
C12 C2 C1 O1 79.8(3)
C12 C2 C3 O3 173.5(2)
C12 C2 C3 C4 -77.1(3)
C12 C2 C3 O4 43.2(3)
C13 C2 C1 N1 18.3(4)
C13 C2 C1 O1 -156.5(2)
C13 C2 C3 O3 46.0(3)
C13 C2 C3 C4 155.4(2)
C13 C2 C3 O4 -84.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303664
