# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa001_0m
_database_code_depnum_ccdc_archive 'CCDC 1429954'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2013-12-06
_audit_creation_method           
; 
  Olex2 1.2 
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466) 
;
_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
_chemical_formula_moiety         'C15 H24 Br N O5'
_chemical_formula_sum            'C15 H24 Br N O5'
_chemical_formula_weight         378.26
_chemical_melting_point          ?
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8508(8)
_cell_length_b                   10.0352(8)
_cell_length_c                   10.7879(9)
_cell_angle_alpha                116.0658(15)
_cell_angle_beta                 107.1142(16)
_cell_angle_gamma                90.5266(17)
_cell_volume                     811.83(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.24
_cell_measurement_theta_min      2.23
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.082
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      99.65
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2538
_reflns_number_total             3029
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 
;
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.000
_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
_refine_special_details          
; 
 ? 
;
_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) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.713
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa002_0m
_database_code_depnum_ccdc_archive 'CCDC 1429955'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2013-12-09
_audit_creation_method           
; 
  Olex2 1.2 
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466) 
;
_chemical_name_common            11
_chemical_name_systematic        
()-(1R,11R,12S)-1,12-Dihydroxy-2,2-dimethyl-5.14-dioxa-4-azabicyclo[9.2.1]tetradecan-3-one
_chemical_formula_moiety         'C13 H21 N O5, C H2 Cl2'
_chemical_formula_sum            'C14 H23 Cl2 N O5'
_chemical_formula_weight         356.23
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7775(8)
_cell_length_b                   8.7429(6)
_cell_length_c                   16.8595(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.8523(13)
_cell_angle_gamma                90
_cell_volume                     1670.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0686 before and 0.0609 after correction. 
The Ratio of minimum to maximum transmission is 0.9022. 
The λ/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.062
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23957
_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         25.497
_diffrn_reflns_theta_min         1.891
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             3102
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 
;
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_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         3102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.000
_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/[σ²(Fo²)+(0.0828P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          
; 
 ? 
;
_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: 
 C5(H5) 
2.b Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A, 
 H11B), C1S(H1SA,H1SB) 
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(H4), O5(H5A) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.55813(17) -0.1649(2) -0.22908(12) 0.0125(4) Uani 1 1 d . . . . .
C2 C -0.46574(17) -0.1403(2) -0.14644(12) 0.0149(4) Uani 1 1 d . . . . .
C3 C -0.47643(18) -0.2719(2) -0.08746(12) 0.0146(4) Uani 1 1 d . . . . .
C4 C -0.59775(18) -0.2849(2) -0.07083(13) 0.0164(5) Uani 1 1 d . . . . .
H4A H -0.6364 -0.1835 -0.0752 0.020 Uiso 1 1 calc R U . . .
H4B H -0.5899 -0.3266 -0.0150 0.020 Uiso 1 1 calc R U . . .
C5 C -0.66967(18) -0.3942(2) -0.13708(12) 0.0135(4) Uani 1 1 d . . . . .
H5A H -0.7398 -0.3406 -0.1733 0.016 Uiso 1 1 calc R U . . .
C6 C -0.57992(17) -0.4353(2) -0.18608(12) 0.0133(4) Uani 1 1 d . . . . .
C7 C -0.59231(18) -0.5927(2) -0.22415(13) 0.0157(4) Uani 1 1 d . . . . .
H7A H -0.6671 -0.5960 -0.2687 0.019 Uiso 1 1 calc R U . . .
H7B H -0.5992 -0.6675 -0.1816 0.019 Uiso 1 1 calc R U . . .
C8 C -0.49225(19) -0.6450(2) -0.26011(14) 0.0207(5) Uani 1 1 d . . . . .
H8A H -0.4189 -0.6510 -0.2144 0.025 Uiso 1 1 calc R U . . .
H8B H -0.5106 -0.7499 -0.2819 0.025 Uiso 1 1 calc R U . . .
C9 C -0.46737(19) -0.5469(2) -0.32816(14) 0.0215(5) Uani 1 1 d . . . . .
H9A H -0.4108 -0.6020 -0.3518 0.026 Uiso 1 1 calc R U . . .
H9B H -0.4290 -0.4510 -0.3034 0.026 Uiso 1 1 calc R U . . .
C10 C -0.5769(2) -0.5061(3) -0.39840(14) 0.0228(5) Uani 1 1 d . . . . .
H10A H -0.5549 -0.5098 -0.4510 0.027 Uiso 1 1 calc R U . . .
H10B H -0.6375 -0.5858 -0.4010 0.027 Uiso 1 1 calc R U . . .
C11 C -0.63206(19) -0.3512(2) -0.39214(12) 0.0188(5) Uani 1 1 d . . . . .
H11A H -0.5715 -0.2712 -0.3890 0.023 Uiso 1 1 calc R U . . .
H11B H -0.6961 -0.3335 -0.4433 0.023 Uiso 1 1 calc R U . . .
C12 C -0.34405(19) -0.1434(3) -0.16391(14) 0.0219(5) Uani 1 1 d . . . . .
H12A H -0.3421 -0.0669 -0.2060 0.033 Uiso 1 1 calc R U . . .
H12B H -0.3300 -0.2451 -0.1837 0.033 Uiso 1 1 calc R U . . .
H12C H -0.2826 -0.1201 -0.1131 0.033 Uiso 1 1 calc R U . . .
C13 C -0.4852(2) 0.0158(2) -0.11170(14) 0.0217(5) Uani 1 1 d . . . . .
H13A H -0.5674 0.0243 -0.1097 0.033 Uiso 1 1 calc R U . . .
H13B H -0.4683 0.0966 -0.1472 0.033 Uiso 1 1 calc R U . . .
H13C H -0.4324 0.0268 -0.0559 0.033 Uiso 1 1 calc R U . . .
N1 N -0.58827(14) -0.31303(19) -0.24946(10) 0.0131(4) Uani 1 1 d . . . . .
O1 O -0.59607(12) -0.05828(15) -0.27674(8) 0.0170(3) Uani 1 1 d . . . . .
O2 O -0.68041(12) -0.33364(15) -0.32182(8) 0.0154(3) Uani 1 1 d . . . . .
O3 O -0.46751(12) -0.41585(15) -0.12912(8) 0.0140(3) Uani 1 1 d . . . . .
O4 O -0.38147(13) -0.26032(16) -0.01838(9) 0.0196(4) Uani 1 1 d . . . . .
H4 H -0.3807 -0.3360 0.0124 0.029 Uiso 1 1 calc R U . . .
O5 O -0.70546(12) -0.52183(15) -0.09807(8) 0.0157(3) Uani 1 1 d . . . . .
H5 H -0.7644 -0.5632 -0.1306 0.024 Uiso 1 1 calc R U . . .
C1S C -0.1866(2) -0.5400(3) -0.06229(16) 0.0300(6) Uani 1 1 d . . . . .
H1SA H -0.1601 -0.5202 -0.0022 0.036 Uiso 1 1 calc R U . . .
H1SB H -0.2660 -0.4946 -0.0840 0.036 Uiso 1 1 calc R U . . .
Cl1S Cl -0.08780(6) -0.45310(8) -0.11042(4) 0.0391(2) Uani 1 1 d . . . . .
Cl2S Cl -0.19448(6) -0.73893(7) -0.07990(5) 0.0454(2) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.531(3) . ?
C1 N1 1.361(3) . ?
C1 O1 1.232(2) . ?
C2 C3 1.548(3) . ?
C2 C12 1.540(3) . ?
C2 C13 1.527(3) . ?
C3 C4 1.534(3) . ?
C3 O3 1.459(2) . ?
C3 O4 1.381(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.537(3) . ?
C5 H5A 1.0000 . ?
C5 C6 1.551(3) . ?
C5 O5 1.416(2) . ?
C6 C7 1.509(3) . ?
C6 N1 1.495(2) . ?
C6 O3 1.417(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.535(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.536(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O2 1.457(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 O2 1.405(2) . ?
O4 H4 0.8400 . ?
O5 H5 0.8400 . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S Cl1S 1.762(2) . ?
C1S Cl2S 1.762(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 115.78(16) . . ?
O1 C1 C2 121.86(17) . . ?
O1 C1 N1 122.14(18) . . ?
C1 C2 C3 108.53(16) . . ?
C1 C2 C12 106.90(16) . . ?
C12 C2 C3 110.68(16) . . ?
C13 C2 C1 109.33(16) . . ?
C13 C2 C3 111.76(17) . . ?
C13 C2 C12 109.50(17) . . ?
C4 C3 C2 114.59(16) . . ?
O3 C3 C2 107.62(15) . . ?
O3 C3 C4 102.53(15) . . ?
O4 C3 C2 107.36(15) . . ?
O4 C3 C4 115.57(16) . . ?
O4 C3 O3 108.71(15) . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C3 C4 C5 105.63(15) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 C6 102.15(15) . . ?
C6 C5 H5A 110.6 . . ?
O5 C5 C4 109.09(15) . . ?
O5 C5 H5A 110.6 . . ?
O5 C5 C6 113.44(16) . . ?
C7 C6 C5 115.90(16) . . ?
N1 C6 C5 107.09(15) . . ?
N1 C6 C7 111.60(16) . . ?
O3 C6 C5 104.94(15) . . ?
O3 C6 C7 111.19(16) . . ?
O3 C6 N1 105.39(15) . . ?
C6 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C6 C7 C8 116.40(17) . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C7 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 C7 117.12(17) . . ?
C9 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.71(18) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 116.06(18) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O2 C11 C10 114.89(17) . . ?
O2 C11 H11A 108.5 . . ?
O2 C11 H11B 108.5 . . ?
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 . . ?
C1 N1 C6 122.52(16) . . ?
C1 N1 O2 115.29(15) . . ?
O2 N1 C6 114.39(14) . . ?
N1 O2 C11 109.82(14) . . ?
C6 O3 C3 104.64(14) . . ?
C3 O4 H4 109.5 . . ?
C5 O5 H5 109.5 . . ?
H1SA C1S H1SB 108.0 . . ?
Cl1S C1S H1SA 109.4 . . ?
Cl1S C1S H1SB 109.4 . . ?
Cl2S C1S H1SA 109.4 . . ?
Cl2S C1S H1SB 109.4 . . ?
Cl2S C1S Cl1S 111.05(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.84 1.96 2.7262(19) 150.3 3_445
O5 H5 O1 0.84 1.93 2.7065(19) 152.4 2_344
O5 H5 O2 0.84 2.52 3.1735(19) 134.9 2_344

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -59.1(2) . . . . ?
C1 C2 C3 O3 54.2(2) . . . . ?
C1 C2 C3 O4 171.05(15) . . . . ?
C1 N1 O2 C11 91.89(18) . . . . ?
C2 C1 N1 C6 27.2(2) . . . . ?
C2 C1 N1 O2 174.67(15) . . . . ?
C2 C3 C4 C5 90.55(19) . . . . ?
C2 C3 O3 C6 -77.61(18) . . . . ?
C3 C4 C5 C6 0.45(19) . . . . ?
C3 C4 C5 O5 120.79(17) . . . . ?
C4 C3 O3 C6 43.58(17) . . . . ?
C4 C5 C6 C7 149.11(17) . . . . ?
C4 C5 C6 N1 -85.62(17) . . . . ?
C4 C5 C6 O3 26.06(18) . . . . ?
C5 C6 C7 C8 -170.03(17) . . . . ?
C5 C6 N1 C1 64.8(2) . . . . ?
C5 C6 N1 O2 -82.97(18) . . . . ?
C5 C6 O3 C3 -44.20(17) . . . . ?
C6 C7 C8 C9 -58.9(3) . . . . ?
C6 N1 O2 C11 -117.97(17) . . . . ?
C7 C6 N1 C1 -167.42(17) . . . . ?
C7 C6 N1 O2 44.8(2) . . . . ?
C7 C6 O3 C3 -170.24(15) . . . . ?
C7 C8 C9 C10 -49.1(3) . . . . ?
C8 C9 C10 C11 96.5(2) . . . . ?
C9 C10 C11 O2 -64.1(2) . . . . ?
C10 C11 O2 N1 75.6(2) . . . . ?
C12 C2 C3 C4 -176.15(16) . . . . ?
C12 C2 C3 O3 -62.8(2) . . . . ?
C12 C2 C3 O4 54.0(2) . . . . ?
C13 C2 C3 C4 61.5(2) . . . . ?
C13 C2 C3 O3 174.82(16) . . . . ?
C13 C2 C3 O4 -68.3(2) . . . . ?
N1 C1 C2 C3 -29.4(2) . . . . ?
N1 C1 C2 C12 90.05(19) . . . . ?
N1 C1 C2 C13 -151.50(17) . . . . ?
N1 C6 C7 C8 67.0(2) . . . . ?
N1 C6 O3 C3 68.69(17) . . . . ?
O1 C1 C2 C3 155.83(18) . . . . ?
O1 C1 C2 C12 -84.8(2) . . . . ?
O1 C1 C2 C13 33.7(2) . . . . ?
O1 C1 N1 C6 -158.01(18) . . . . ?
O1 C1 N1 O2 -10.5(3) . . . . ?
O3 C3 C4 C5 -25.73(19) . . . . ?
O3 C6 C7 C8 -50.3(2) . . . . ?
O3 C6 N1 C1 -46.6(2) . . . . ?
O3 C6 N1 O2 165.66(13) . . . . ?
O4 C3 C4 C5 -143.80(16) . . . . ?
O4 C3 O3 C6 166.41(15) . . . . ?
O5 C5 C6 C7 31.9(2) . . . . ?
O5 C5 C6 N1 157.12(15) . . . . ?
O5 C5 C6 O3 -91.20(18) . . . . ?

_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.836
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa004_0m
_database_code_depnum_ccdc_archive 'CCDC 1429956'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2013-12-09
_audit_creation_method           
; 
  Olex2 1.2 
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466) 
;
_chemical_name_common            10
_chemical_name_systematic        
; 
()-10,10-dimethylhexahydro-2H-pyrrolo[1,2-b][1,2]oxazecine-7,9,11(10H)-trione 
;
_chemical_formula_moiety         'C13 H19 N O4'
_chemical_formula_sum            'C13 H19 N O4'
_chemical_formula_weight         253.29
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3134(5)
_cell_length_b                   9.4290(4)
_cell_length_c                   12.7345(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.9907(8)
_cell_angle_gamma                90
_cell_volume                     1268.29(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.76
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0634 before and 0.0501 after correction. 
The Ratio of minimum to maximum transmission is 0.9341. 
The λ/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.158
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0265
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21397
_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         27.590
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2412
_reflns_number_total             2947
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 
;
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_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     165
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2445P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2501
_refine_ls_wR_factor_ref         0.2774
_refine_special_details          
; 
 ? 
;
_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: 
 C4(H4) 
2.b Secondary CH2 refined with riding coordinates: 
 C5(H5a,H5b), 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) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72843(18) 0.89976(18) 0.30557(16) 0.0148(5) Uani 1 1 d . . . . .
C2 C 0.66373(19) 0.8401(2) 0.38229(17) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.7748(2) 0.8025(2) 0.48858(19) 0.0242(5) Uani 1 1 d . . . . .
C4 C 0.9000(2) 0.8257(2) 0.47210(18) 0.0220(5) Uani 1 1 d . . . . .
H4 H 0.9476 0.9060 0.5201 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9821(2) 0.6941(2) 0.4933(2) 0.0243(5) Uani 1 1 d . . . . .
H5A H 0.9405 0.6215 0.4358 0.029 Uiso 1 1 calc R U . . .
H5B H 0.9927 0.6544 0.5681 0.029 Uiso 1 1 calc R U . . .
C6 C 1.1123(2) 0.7312(2) 0.48856(18) 0.0224(5) Uani 1 1 d . . . . .
C7 C 1.1594(2) 0.6372(2) 0.41780(19) 0.0256(5) Uani 1 1 d . . . . .
H7A H 1.0857 0.5944 0.3583 0.031 Uiso 1 1 calc R U . . .
H7B H 1.2089 0.5590 0.4654 0.031 Uiso 1 1 calc R U . . .
C8 C 1.2411(2) 0.7102(2) 0.3626(2) 0.0254(5) Uani 1 1 d . . . . .
H8A H 1.2569 0.6423 0.3098 0.030 Uiso 1 1 calc R U . . .
H8B H 1.3239 0.7318 0.4217 0.030 Uiso 1 1 calc R U . . .
C9 C 1.1892(2) 0.8477(2) 0.29793(19) 0.0212(5) Uani 1 1 d . . . . .
H9A H 1.2547 0.8867 0.2713 0.025 Uiso 1 1 calc R U . . .
H9B H 1.1772 0.9171 0.3517 0.025 Uiso 1 1 calc R U . . .
C10 C 1.0642(2) 0.8383(2) 0.19631(18) 0.0219(5) Uani 1 1 d . . . . .
H10A H 1.0530 0.9283 0.1538 0.026 Uiso 1 1 calc R U . . .
H10B H 1.0730 0.7618 0.1464 0.026 Uiso 1 1 calc R U . . .
C11 C 0.94454(19) 0.8109(2) 0.22063(17) 0.0196(5) Uani 1 1 d . . . . .
H11A H 0.8692 0.8250 0.1516 0.024 Uiso 1 1 calc R U . . .
H11B H 0.9438 0.7120 0.2466 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5915(2) 0.7047(2) 0.3305(2) 0.0299(6) Uani 1 1 d . . . . .
H12A H 0.5182 0.7292 0.2636 0.045 Uiso 1 1 calc R U . . .
H12B H 0.5627 0.6575 0.3855 0.045 Uiso 1 1 calc R U . . .
H12C H 0.6475 0.6409 0.3091 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5762(2) 0.9474(2) 0.4074(2) 0.0230(5) Uani 1 1 d . . . . .
H13A H 0.6243 1.0329 0.4406 0.035 Uiso 1 1 calc R U . . .
H13B H 0.5409 0.9058 0.4604 0.035 Uiso 1 1 calc R U . . .
H13C H 0.5072 0.9723 0.3375 0.035 Uiso 1 1 calc R U . . .
N1 N 0.85231(15) 0.86700(17) 0.35266(14) 0.0153(4) Uani 1 1 d . . . . .
O1 O 0.67769(13) 0.96054(15) 0.21549(12) 0.0193(4) Uani 1 1 d . . . . .
O2 O 0.94205(13) 0.91011(14) 0.30789(12) 0.0161(4) Uani 1 1 d . . . . .
O3 O 1.17417(15) 0.83258(17) 0.53988(13) 0.0277(5) Uani 1 1 d . . . . .
O4 O 0.76755(17) 0.7588(2) 0.57521(15) 0.0384(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.523(3) . ?
C1 N1 1.348(2) . ?
C1 O1 1.226(2) . ?
C2 C3 1.522(3) . ?
C2 C12 1.532(3) . ?
C2 C13 1.528(3) . ?
C3 C4 1.521(3) . ?
C3 O4 1.208(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.515(3) . ?
C4 N1 1.472(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.536(3) . ?
C6 C7 1.492(3) . ?
C6 O3 1.226(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.535(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.539(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O2 1.461(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 O2 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 106.98(16) . . ?
O1 C1 C2 126.99(18) . . ?
O1 C1 N1 125.96(18) . . ?
C1 C2 C3 102.89(16) . . ?
C1 C2 C12 109.64(17) . . ?
C1 C2 C13 112.73(16) . . ?
C3 C2 C12 109.40(18) . . ?
C3 C2 C13 111.00(17) . . ?
C13 C2 C12 110.87(18) . . ?
C4 C3 C2 110.90(17) . . ?
O4 C3 C2 125.95(19) . . ?
O4 C3 C4 123.1(2) . . ?
C3 C4 H4 110.4 . . ?
C5 C4 C3 113.52(18) . . ?
C5 C4 H4 110.4 . . ?
N1 C4 C3 99.53(16) . . ?
N1 C4 H4 110.4 . . ?
N1 C4 C5 112.02(17) . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.98(17) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C7 C6 C5 116.35(18) . . ?
O3 C6 C5 121.9(2) . . ?
O3 C6 C7 121.7(2) . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C6 C7 C8 114.85(18) . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 108.0 . . ?
C7 C8 H8B 108.1 . . ?
C7 C8 C9 116.98(18) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.0 . . ?
C8 C9 H9A 107.9 . . ?
C8 C9 H9B 107.9 . . ?
C8 C9 C10 117.52(17) . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C9 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 C9 117.16(18) . . ?
C11 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O2 C11 C10 107.96(16) . . ?
O2 C11 H11A 110.1 . . ?
O2 C11 H11B 110.1 . . ?
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 . . ?
C1 N1 C4 117.27(16) . . ?
C1 N1 O2 123.08(16) . . ?
O2 N1 C4 116.69(15) . . ?
N1 O2 C11 109.90(14) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -5.1(2) . . . . ?
C1 C2 C3 O4 175.5(2) . . . . ?
C1 N1 O2 C11 -84.4(2) . . . . ?
C2 C1 N1 C4 -17.3(2) . . . . ?
C2 C1 N1 O2 -177.18(15) . . . . ?
C2 C3 C4 C5 -122.85(19) . . . . ?
C2 C3 C4 N1 -3.7(2) . . . . ?
C3 C4 C5 C6 -173.32(18) . . . . ?
C3 C4 N1 C1 13.3(2) . . . . ?
C3 C4 N1 O2 174.44(15) . . . . ?
C4 C5 C6 C7 -131.33(19) . . . . ?
C4 C5 C6 O3 48.5(3) . . . . ?
C4 N1 O2 C11 115.67(18) . . . . ?
C5 C4 N1 C1 133.60(19) . . . . ?
C5 C4 N1 O2 -65.3(2) . . . . ?
C5 C6 C7 C8 148.0(2) . . . . ?
C6 C7 C8 C9 -50.0(3) . . . . ?
C7 C8 C9 C10 -61.7(3) . . . . ?
C8 C9 C10 C11 70.3(3) . . . . ?
C9 C10 C11 O2 49.0(2) . . . . ?
C10 C11 O2 N1 -165.31(15) . . . . ?
C12 C2 C3 C4 111.4(2) . . . . ?
C12 C2 C3 O4 -68.0(3) . . . . ?
C13 C2 C3 C4 -125.91(19) . . . . ?
C13 C2 C3 O4 54.7(3) . . . . ?
N1 C1 C2 C3 12.72(19) . . . . ?
N1 C1 C2 C12 -103.6(2) . . . . ?
N1 C1 C2 C13 132.36(18) . . . . ?
N1 C4 C5 C6 74.9(2) . . . . ?
O1 C1 C2 C3 -170.25(19) . . . . ?
O1 C1 C2 C12 73.4(2) . . . . ?
O1 C1 C2 C13 -50.6(3) . . . . ?
O1 C1 N1 C4 165.59(18) . . . . ?
O1 C1 N1 O2 5.8(3) . . . . ?
O3 C6 C7 C8 -31.9(3) . . . . ?
O4 C3 C4 C5 56.6(3) . . . . ?
O4 C3 C4 N1 175.8(2) . . . . ?

_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.973
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa005_0ma
_database_code_depnum_ccdc_archive 'CCDC 1429957'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_vrf_PLAT113_aa005_0ma           
; 
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space-group.       P2/c 
RESPONSE: The ADDSYM option in Platon did not give P2/c as a possible space group. 
;
_audit_creation_date             2013-12-16
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) 
;
_shelxl_version_number           2013-4
_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 
;
_chemical_formula_moiety         '2(C15 H21 N O4)'
_chemical_formula_sum            'C30 H42 N2 O8'
_chemical_formula_weight         558.65
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.0197(5)
_cell_length_b                   16.2710(5)
_cell_length_c                   10.1414(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.0774(5)
_cell_angle_gamma                90
_cell_volume                     2773.26(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.976
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.155
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4309
_reflns_number_total             5170
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.000
_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/[σ²(Fo²)+(0.0987P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          
; 
 ? 
;
_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) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.3866(9) 0.4909(10) 1.1165(16) 0.017(4) Uiso 1 1 d . . . . .
C1 C 0.38690(8) 0.52593(8) 0.93113(12) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.38006(8) 0.61823(8) 0.96568(12) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.29643(8) 0.62943(8) 0.99380(13) 0.0132(3) Uani 1 1 d . . . . .
C4 C 0.26314(8) 0.67207(8) 1.08450(13) 0.0141(3) Uani 1 1 d . . . . .
H4 H 0.2896 0.7091 1.1492 0.017 Uiso 1 1 calc R . . . .
C5 C 0.17978(8) 0.65097(8) 1.06503(13) 0.0147(3) Uani 1 1 d . . . . .
C6 C 0.16832(8) 0.59545(8) 0.96251(13) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.09892(8) 0.54736(9) 0.89603(14) 0.0199(3) Uani 1 1 d . . . . .
H7A H 0.0756 0.5765 0.8133 0.024 Uiso 1 1 calc R . . . .
H7B H 0.0581 0.5463 0.9556 0.024 Uiso 1 1 calc R . . . .
C8 C 0.11679(8) 0.45849(9) 0.85964(13) 0.0178(3) Uani 1 1 d . . . . .
H8A H 0.0684 0.4353 0.8053 0.021 Uiso 1 1 calc R . . . .
H8B H 0.1590 0.4595 0.8028 0.021 Uiso 1 1 calc R . . . .
C9 C 0.14312(8) 0.40024(9) 0.97735(14) 0.0186(3) Uani 1 1 d . . . . .
H9A H 0.1084 0.4102 1.0454 0.022 Uiso 1 1 calc R . . . .
H9B H 0.1333 0.3432 0.9450 0.022 Uiso 1 1 calc R . . . .
C10 C 0.22991(8) 0.40601(9) 1.04646(13) 0.0170(3) Uani 1 1 d . . . . .
H10A H 0.2416 0.4632 1.0767 0.020 Uiso 1 1 calc R . . . .
H10B H 0.2376 0.3700 1.1262 0.020 Uiso 1 1 calc R . . . .
C11 C 0.28750(8) 0.38059(9) 0.95334(13) 0.0162(3) Uani 1 1 d . . . . .
H11A H 0.2781 0.3221 0.9288 0.019 Uiso 1 1 calc R . . . .
H11B H 0.2762 0.4135 0.8704 0.019 Uiso 1 1 calc R . . . .
C12 C 0.39397(9) 0.67047(9) 0.84493(13) 0.0189(3) Uani 1 1 d . . . . .
H12A H 0.3558 0.6544 0.7665 0.028 Uiso 1 1 calc GR . . . .
H12B H 0.4482 0.6615 0.8270 0.028 Uiso 1 1 calc GR . . . .
H12C H 0.3867 0.7287 0.8645 0.028 Uiso 1 1 calc GR . . . .
C13 C 0.43955(8) 0.64357(9) 1.08871(13) 0.0171(3) Uani 1 1 d . . . . .
H13A H 0.4348 0.7027 1.1042 0.026 Uiso 1 1 calc GR . . . .
H13B H 0.4937 0.6310 1.0736 0.026 Uiso 1 1 calc GR . . . .
H13C H 0.4281 0.6132 1.1670 0.026 Uiso 1 1 calc GR . . . .
C14 C 0.11785(8) 0.68376(9) 1.13650(13) 0.0170(3) Uani 1 1 d . . . . .
C15 C 0.13944(9) 0.75503(9) 1.22910(15) 0.0221(3) Uani 1 1 d . . . . .
H15A H 0.1377 0.8060 1.1771 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.1932 0.7470 1.2784 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.1015 0.7586 1.2922 0.033 Uiso 1 1 calc GR . . . .
N1 N 0.38669(7) 0.47496(7) 1.03512(11) 0.0141(3) Uani 1 1 d . . . . .
O1 O 0.38727(6) 0.50153(6) 0.81682(9) 0.0181(2) Uani 1 1 d . . . . .
O2 O 0.37076(6) 0.39124(6) 1.01110(9) 0.0165(2) Uani 1 1 d . . . . .
O3 O 0.23839(5) 0.58352(6) 0.91567(9) 0.0145(2) Uani 1 1 d . . . . .
O4 O 0.04958(6) 0.65690(6) 1.11904(10) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.3865(9) 0.5050(10) 0.6195(16) 0.018(4) Uiso 1 1 d . . . . .
C16 C 0.38997(8) 0.47400(8) 0.43225(12) 0.0131(3) Uani 1 1 d . . . . .
C17 C 0.39265(8) 0.38129(8) 0.46774(12) 0.0134(3) Uani 1 1 d . . . . .
C18 C 0.31057(8) 0.36190(8) 0.49535(12) 0.0128(3) Uani 1 1 d . . . . .
C19 C 0.28067(8) 0.32225(8) 0.59290(13) 0.0138(3) Uani 1 1 d . . . . .
H19 H 0.3102 0.2940 0.6665 0.017 Uiso 1 1 calc R . . . .
C20 C 0.19524(8) 0.33083(8) 0.56447(13) 0.0138(3) Uani 1 1 d . . . . .
C21 C 0.17937(8) 0.37711(8) 0.45098(13) 0.0147(3) Uani 1 1 d . . . . .
C22 C 0.10774(8) 0.41585(9) 0.37095(14) 0.0205(3) Uani 1 1 d . . . . .
H22A H 0.0620 0.4092 0.4193 0.025 Uiso 1 1 calc R . . . .
H22B H 0.0950 0.3865 0.2847 0.025 Uiso 1 1 calc R . . . .
C23 C 0.11845(9) 0.50746(9) 0.34321(14) 0.0226(3) Uani 1 1 d . . . . .
H23A H 0.0696 0.5276 0.2862 0.027 Uiso 1 1 calc R . . . .
H23B H 0.1629 0.5135 0.2917 0.027 Uiso 1 1 calc R . . . .
C24 C 0.13530(9) 0.56273(10) 0.46740(15) 0.0248(4) Uani 1 1 d . . . . .
H24A H 0.1188 0.6194 0.4404 0.030 Uiso 1 1 calc R . . . .
H24B H 0.1011 0.5441 0.5320 0.030 Uiso 1 1 calc R . . . .
C25 C 0.22167(9) 0.56577(9) 0.54009(14) 0.0211(3) Uani 1 1 d . . . . .
H25A H 0.2236 0.5968 0.6246 0.025 Uiso 1 1 calc R . . . .
H25B H 0.2404 0.5092 0.5627 0.025 Uiso 1 1 calc R . . . .
C26 C 0.27662(9) 0.60618(9) 0.45542(14) 0.0199(3) Uani 1 1 d . . . . .
H26A H 0.2706 0.5779 0.3679 0.024 Uiso 1 1 calc R . . . .
H26B H 0.2597 0.6640 0.4388 0.024 Uiso 1 1 calc R . . . .
C27 C 0.41179(9) 0.33215(9) 0.34731(13) 0.0182(3) Uani 1 1 d . . . . .
H27A H 0.4114 0.2733 0.3675 0.027 Uiso 1 1 calc GR . . . .
H27B H 0.4645 0.3480 0.3285 0.027 Uiso 1 1 calc GR . . . .
H27C H 0.3717 0.3439 0.2691 0.027 Uiso 1 1 calc GR . . . .
C28 C 0.45320(8) 0.36102(9) 0.59180(13) 0.0168(3) Uani 1 1 d . . . . .
H28A H 0.4392 0.3907 0.6689 0.025 Uiso 1 1 calc GR . . . .
H28B H 0.5065 0.3776 0.5770 0.025 Uiso 1 1 calc GR . . . .
H28C H 0.4527 0.3018 0.6089 0.025 Uiso 1 1 calc GR . . . .
C29 C 0.14148(8) 0.29136(9) 0.64538(13) 0.0170(3) Uani 1 1 d . . . . .
C30 C 0.05267(9) 0.29473(11) 0.60279(15) 0.0280(4) Uani 1 1 d . . . . .
H30A H 0.0267 0.2599 0.6619 0.042 Uiso 1 1 calc GR . . . .
H30B H 0.0393 0.2749 0.5107 0.042 Uiso 1 1 calc GR . . . .
H30C H 0.0343 0.3515 0.6080 0.042 Uiso 1 1 calc GR . . . .
N2 N 0.38607(7) 0.52385(7) 0.53717(11) 0.0150(3) Uani 1 1 d . . . . .
O5 O 0.38600(6) 0.49979(6) 0.31787(9) 0.0181(2) Uani 1 1 d . . . . .
O6 O 0.36011(6) 0.60514(6) 0.51433(9) 0.0180(2) Uani 1 1 d . . . . .
O7 O 0.24868(5) 0.39542(6) 0.40612(9) 0.0146(2) Uani 1 1 d . . . . .
O8 O 0.16927(6) 0.25398(6) 0.74624(10) 0.0228(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5508(19) . ?
C1 N1 1.3421(17) . ?
C1 O1 1.2263(15) . ?
C2 C3 1.5062(18) . ?
C2 C12 1.5393(18) . ?
C2 C13 1.5341(18) . ?
C3 C4 1.3463(18) . ?
C3 O3 1.3837(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.4426(19) . ?
C5 C6 1.3680(19) . ?
C5 C14 1.4704(19) . ?
C6 C7 1.4868(19) . ?
C6 O3 1.3655(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5345(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5348(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5347(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5218(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O2 1.4557(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.501(2) . ?
C14 O4 1.2277(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1 0.865(15) . ?
N1 O2 1.4028(15) . ?
C16 C17 1.5499(19) . ?
C16 N2 1.3478(17) . ?
C16 O5 1.2253(15) . ?
C17 C18 1.5009(18) . ?
C17 C27 1.5371(18) . ?
C17 C28 1.5313(18) . ?
C18 C19 1.3465(18) . ?
C18 O7 1.3875(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.4438(19) . ?
C20 C21 1.3663(19) . ?
C20 C29 1.4695(19) . ?
C21 C22 1.4933(18) . ?
C21 O7 1.3626(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.533(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.537(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.538(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.516(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 O6 1.4520(17) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.506(2) . ?
C29 O8 1.2195(17) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N2 H2 0.888(16) . ?
N2 O6 1.4022(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 114.29(11) . . ?
O1 C1 C2 122.61(11) . . ?
O1 C1 N1 122.95(13) . . ?
C3 C2 C1 105.48(10) . . ?
C3 C2 C12 110.63(11) . . ?
C3 C2 C13 109.61(11) . . ?
C12 C2 C1 109.18(10) . . ?
C13 C2 C1 112.37(11) . . ?
C13 C2 C12 109.51(11) . . ?
C4 C3 C2 134.73(12) . . ?
C4 C3 O3 109.27(11) . . ?
O3 C3 C2 115.90(11) . . ?
C3 C4 H4 126.4 . . ?
C3 C4 C5 107.14(12) . . ?
C5 C4 H4 126.4 . . ?
C4 C5 C14 127.75(12) . . ?
C6 C5 C4 106.29(11) . . ?
C6 C5 C14 125.93(13) . . ?
C5 C6 C7 134.44(13) . . ?
O3 C6 C5 109.30(11) . . ?
O3 C6 C7 116.26(12) . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C6 C7 C8 115.57(12) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C7 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 C7 116.07(11) . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 C8 117.34(11) . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.57(11) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O2 C11 C10 113.53(11) . . ?
O2 C11 H11A 108.9 . . ?
O2 C11 H11B 108.9 . . ?
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 . . ?
C5 C14 C15 117.71(12) . . ?
O4 C14 C5 122.38(13) . . ?
O4 C14 C15 119.85(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 H1 124.4(10) . . ?
C1 N1 O2 119.21(11) . . ?
O2 N1 H1 115.2(10) . . ?
N1 O2 C11 109.55(9) . . ?
C6 O3 C3 107.93(10) . . ?
N2 C16 C17 113.93(11) . . ?
O5 C16 C17 123.26(11) . . ?
O5 C16 N2 122.62(13) . . ?
C18 C17 C16 104.70(10) . . ?
C18 C17 C27 111.04(11) . . ?
C18 C17 C28 109.09(11) . . ?
C27 C17 C16 108.90(10) . . ?
C28 C17 C16 113.06(11) . . ?
C28 C17 C27 109.95(11) . . ?
C19 C18 C17 135.12(12) . . ?
C19 C18 O7 109.36(12) . . ?
O7 C18 C17 115.40(11) . . ?
C18 C19 H19 126.5 . . ?
C18 C19 C20 107.00(12) . . ?
C20 C19 H19 126.5 . . ?
C19 C20 C29 122.84(12) . . ?
C21 C20 C19 106.29(12) . . ?
C21 C20 C29 130.80(13) . . ?
C20 C21 C22 136.59(13) . . ?
O7 C21 C20 109.59(12) . . ?
O7 C21 C22 113.69(11) . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C21 C22 C23 113.56(12) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 108.4 . . ?
C22 C23 H23B 108.4 . . ?
C22 C23 C24 115.51(12) . . ?
H23A C23 H23B 107.5 . . ?
C24 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
C23 C24 H24A 108.1 . . ?
C23 C24 H24B 108.1 . . ?
H24A C24 H24B 107.3 . . ?
C25 C24 C23 116.88(12) . . ?
C25 C24 H24A 108.1 . . ?
C25 C24 H24B 108.1 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 C24 111.78(12) . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O6 C26 C25 114.40(11) . . ?
O6 C26 H26A 108.7 . . ?
O6 C26 H26B 108.7 . . ?
C17 C27 H27A 109.5 . . ?
C17 C27 H27B 109.5 . . ?
C17 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C28 H28A 109.5 . . ?
C17 C28 H28B 109.5 . . ?
C17 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C29 C30 120.60(12) . . ?
O8 C29 C20 119.54(13) . . ?
O8 C29 C30 119.84(13) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C16 N2 H2 122.7(10) . . ?
C16 N2 O6 119.38(11) . . ?
O6 N2 H2 115.9(10) . . ?
N2 O6 C26 109.96(10) . . ?
C21 O7 C18 107.73(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.888(16) 2.000(16) 2.8561(14) 161.4(14) .

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 139.45(15) . . . . ?
C1 C2 C3 O3 -36.54(14) . . . . ?
C1 N1 O2 C11 -69.89(14) . . . . ?
C2 C1 N1 O2 162.72(11) . . . . ?
C2 C3 C4 C5 -174.97(14) . . . . ?
C2 C3 O3 C6 174.53(11) . . . . ?
C3 C4 C5 C6 0.46(15) . . . . ?
C3 C4 C5 C14 -177.64(13) . . . . ?
C4 C3 O3 C6 -2.45(14) . . . . ?
C4 C5 C6 C7 177.35(15) . . . . ?
C4 C5 C6 O3 -1.98(14) . . . . ?
C4 C5 C14 C15 8.4(2) . . . . ?
C4 C5 C14 O4 -174.28(13) . . . . ?
C5 C6 C7 C8 -139.94(15) . . . . ?
C5 C6 O3 C3 2.75(14) . . . . ?
C6 C5 C14 C15 -169.32(13) . . . . ?
C6 C5 C14 O4 8.0(2) . . . . ?
C6 C7 C8 C9 65.89(17) . . . . ?
C7 C6 O3 C3 -176.71(11) . . . . ?
C7 C8 C9 C10 -78.69(16) . . . . ?
C8 C9 C10 C11 -65.24(16) . . . . ?
C9 C10 C11 O2 175.43(11) . . . . ?
C10 C11 O2 N1 -63.93(13) . . . . ?
C12 C2 C3 C4 -102.60(17) . . . . ?
C12 C2 C3 O3 81.41(14) . . . . ?
C13 C2 C3 C4 18.3(2) . . . . ?
C13 C2 C3 O3 -157.73(11) . . . . ?
C14 C5 C6 C7 -4.5(2) . . . . ?
C14 C5 C6 O3 176.16(12) . . . . ?
N1 C1 C2 C3 -69.78(14) . . . . ?
N1 C1 C2 C12 171.31(11) . . . . ?
N1 C1 C2 C13 49.60(15) . . . . ?
O1 C1 C2 C3 105.74(14) . . . . ?
O1 C1 C2 C12 -13.17(18) . . . . ?
O1 C1 C2 C13 -134.88(13) . . . . ?
O1 C1 N1 O2 -12.78(19) . . . . ?
O3 C3 C4 C5 1.21(15) . . . . ?
O3 C6 C7 C8 39.35(17) . . . . ?
C16 C17 C18 C19 -131.99(16) . . . . ?
C16 C17 C18 O7 43.45(14) . . . . ?
C16 N2 O6 C26 67.12(14) . . . . ?
C17 C16 N2 O6 -161.31(11) . . . . ?
C17 C18 C19 C20 175.67(14) . . . . ?
C17 C18 O7 C21 -175.60(11) . . . . ?
C18 C19 C20 C21 -1.04(15) . . . . ?
C18 C19 C20 C29 176.39(12) . . . . ?
C19 C18 O7 C21 0.99(14) . . . . ?
C19 C20 C21 C22 -173.68(15) . . . . ?
C19 C20 C21 O7 1.67(14) . . . . ?
C19 C20 C29 C30 -173.32(13) . . . . ?
C19 C20 C29 O8 5.0(2) . . . . ?
C20 C21 C22 C23 127.86(17) . . . . ?
C20 C21 O7 C18 -1.67(14) . . . . ?
C21 C20 C29 C30 3.4(2) . . . . ?
C21 C20 C29 O8 -178.26(13) . . . . ?
C21 C22 C23 C24 -60.99(17) . . . . ?
C22 C21 O7 C18 174.84(11) . . . . ?
C22 C23 C24 C25 81.49(17) . . . . ?
C23 C24 C25 C26 66.81(16) . . . . ?
C24 C25 C26 O6 -175.40(11) . . . . ?
C25 C26 O6 N2 59.28(14) . . . . ?
C27 C17 C18 C19 110.64(17) . . . . ?
C27 C17 C18 O7 -73.93(14) . . . . ?
C28 C17 C18 C19 -10.7(2) . . . . ?
C28 C17 C18 O7 164.74(11) . . . . ?
C29 C20 C21 C22 9.2(3) . . . . ?
C29 C20 C21 O7 -175.48(13) . . . . ?
N2 C16 C17 C18 71.06(13) . . . . ?
N2 C16 C17 C27 -170.11(11) . . . . ?
N2 C16 C17 C28 -47.57(15) . . . . ?
O5 C16 C17 C18 -103.99(14) . . . . ?
O5 C16 C17 C27 14.84(18) . . . . ?
O5 C16 C17 C28 137.38(13) . . . . ?
O5 C16 N2 O6 13.77(19) . . . . ?
O7 C18 C19 C20 0.04(14) . . . . ?
O7 C21 C22 C23 -47.36(16) . . . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa006_0m
_database_code_depnum_ccdc_archive 'CCDC 1429958'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2013-12-17
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736) 
;
_shelxl_version_number           2013-4
_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
_chemical_formula_moiety         'C13 H19 N O5'
_chemical_formula_sum            'C13 H19 N O5'
_chemical_formula_weight         269.29
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9816(5)
_cell_length_b                   9.2222(4)
_cell_length_c                   13.0751(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.6889(8)
_cell_angle_gamma                90
_cell_volume                     1261.57(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4747
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.973
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.067
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             2898
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.000
_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/[σ²(Fo²)+(0.1017P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          
; 
 ? 
;
_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) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35651(13) 0.28955(17) 0.70018(11) 0.0121(3) Uani 1 1 d . . . . .
C2 C 0.40959(13) 0.35851(17) 0.81261(11) 0.0123(3) Uani 1 1 d . . . . .
C3 C 0.52883(13) 0.27380(17) 0.87923(11) 0.0130(3) Uani 1 1 d . . . . .
C4 C 0.49728(14) 0.11593(18) 0.89264(12) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.4252 0.0887 0.9206 0.020 Uiso 1 1 calc R . . . .
C5 C 0.52045(14) 0.03728(18) 0.80361(12) 0.0155(3) Uani 1 1 d . . . . .
H5 H 0.4645 -0.0453 0.7681 0.019 Uiso 1 1 calc R . . . .
C6 C 0.56178(13) 0.15360(16) 0.73746(11) 0.0116(3) Uani 1 1 d . . . . .
C7 C 0.65621(13) 0.10701(17) 0.68080(12) 0.0146(3) Uani 1 1 d . . . . .
H7A H 0.6116 0.0420 0.6209 0.018 Uiso 1 1 calc R . . . .
H7B H 0.7242 0.0495 0.7317 0.018 Uiso 1 1 calc R . . . .
C8 C 0.71956(14) 0.22860(18) 0.63585(12) 0.0174(3) Uani 1 1 d . . . . .
H8A H 0.7793 0.1840 0.6015 0.021 Uiso 1 1 calc R . . . .
H8B H 0.7712 0.2878 0.6968 0.021 Uiso 1 1 calc R . . . .
C9 C 0.63008(14) 0.33065(18) 0.55419(12) 0.0174(3) Uani 1 1 d . . . . .
H9A H 0.6823 0.3932 0.5224 0.021 Uiso 1 1 calc R . . . .
H9B H 0.5861 0.3944 0.5926 0.021 Uiso 1 1 calc R . . . .
C10 C 0.52852(15) 0.25317(18) 0.46275(12) 0.0171(3) Uani 1 1 d . . . . .
H10A H 0.5192 0.3067 0.3952 0.021 Uiso 1 1 calc R . . . .
H10B H 0.5603 0.1549 0.4542 0.021 Uiso 1 1 calc R . . . .
C11 C 0.39755(14) 0.23868(17) 0.47791(11) 0.0141(3) Uani 1 1 d . . . . .
H11A H 0.3679 0.3362 0.4913 0.017 Uiso 1 1 calc R . . . .
H11B H 0.3371 0.2019 0.4103 0.017 Uiso 1 1 calc R . . . .
C12 C 0.44698(15) 0.51544(17) 0.79528(12) 0.0164(3) Uani 1 1 d . . . . .
H12A H 0.4738 0.5663 0.8643 0.025 Uiso 1 1 calc GR . . . .
H12B H 0.3733 0.5654 0.7464 0.025 Uiso 1 1 calc GR . . . .
H12C H 0.5176 0.5145 0.7641 0.025 Uiso 1 1 calc GR . . . .
C13 C 0.30570(14) 0.35900(19) 0.86865(12) 0.0173(3) Uani 1 1 d . . . . .
H13A H 0.2732 0.2602 0.8700 0.026 Uiso 1 1 calc GR . . . .
H13B H 0.2356 0.4226 0.8295 0.026 Uiso 1 1 calc GR . . . .
H13C H 0.3418 0.3944 0.9424 0.026 Uiso 1 1 calc GR . . . .
N1 N 0.44245(11) 0.21530(14) 0.66347(9) 0.0117(3) Uani 1 1 d . . . . .
O1 O 0.24580(10) 0.31103(13) 0.64410(8) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.39273(9) 0.14322(11) 0.56517(8) 0.0128(3) Uani 1 1 d . . . . .
O3 O 0.61363(9) 0.26374(11) 0.81279(8) 0.0119(3) Uani 1 1 d . . . . .
O4 O 0.58960(10) 0.34900(13) 0.97128(8) 0.0182(3) Uani 1 1 d . . . . .
H4A H 0.6393 0.2931 1.0154 0.027 Uiso 1 1 calc GR . . . .
O5 O 0.60841(10) 0.02317(13) 0.90999(9) 0.0192(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5442(19) . ?
C1 N1 1.3658(18) . ?
C1 O1 1.2301(17) . ?
C2 C3 1.5462(19) . ?
C2 C12 1.540(2) . ?
C2 C13 1.5318(19) . ?
C3 C4 1.519(2) . ?
C3 O3 1.4567(17) . ?
C3 O4 1.3736(18) . ?
C4 H4 1.0000 . ?
C4 C5 1.458(2) . ?
C4 O5 1.4506(18) . ?
C5 H5 1.0000 . ?
C5 C6 1.531(2) . ?
C5 O5 1.4381(18) . ?
C6 C7 1.5085(19) . ?
C6 N1 1.4854(17) . ?
C6 O3 1.4090(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.534(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.541(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O2 1.4547(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 O2 1.4020(15) . ?
O4 H4A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 116.09(12) . . ?
O1 C1 C2 121.33(13) . . ?
O1 C1 N1 122.32(13) . . ?
C1 C2 C3 109.78(12) . . ?
C12 C2 C1 106.70(11) . . ?
C12 C2 C3 109.86(12) . . ?
C13 C2 C1 109.63(12) . . ?
C13 C2 C3 111.00(12) . . ?
C13 C2 C12 109.77(13) . . ?
C4 C3 C2 111.44(12) . . ?
O3 C3 C2 106.36(11) . . ?
O3 C3 C4 102.55(12) . . ?
O4 C3 C2 109.96(12) . . ?
O4 C3 C4 116.74(12) . . ?
O4 C3 O3 109.04(12) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 106.46(12) . . ?
C5 C4 H4 121.1 . . ?
O5 C4 C3 111.88(12) . . ?
O5 C4 H4 121.1 . . ?
O5 C4 C5 59.26(9) . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 104.84(13) . . ?
C6 C5 H5 121.2 . . ?
O5 C5 C4 60.11(9) . . ?
O5 C5 H5 121.2 . . ?
O5 C5 C6 112.49(12) . . ?
C7 C6 C5 116.35(13) . . ?
N1 C6 C5 106.38(11) . . ?
N1 C6 C7 113.04(12) . . ?
O3 C6 C5 103.67(12) . . ?
O3 C6 C7 110.89(12) . . ?
O3 C6 N1 105.56(11) . . ?
C6 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C6 C7 C8 116.17(13) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C7 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C7 C8 C9 116.59(12) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.52(13) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.55(13) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O2 C11 C10 114.70(12) . . ?
O2 C11 H11A 108.6 . . ?
O2 C11 H11B 108.6 . . ?
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 . . ?
C1 N1 C6 122.02(11) . . ?
C1 N1 O2 116.21(11) . . ?
O2 N1 C6 115.86(11) . . ?
N1 O2 C11 109.58(10) . . ?
C6 O3 C3 105.49(11) . . ?
C3 O4 H4A 109.5 . . ?
C5 O5 C4 60.63(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O1 0.84 1.98 2.8055(15) 166.9 4_666

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -59.70(15) . . . . ?
C1 C2 C3 O3 51.31(15) . . . . ?
C1 C2 C3 O4 169.24(11) . . . . ?
C1 N1 O2 C11 91.21(14) . . . . ?
C2 C1 N1 C6 23.5(2) . . . . ?
C2 C1 N1 O2 175.26(11) . . . . ?
C2 C3 C4 C5 91.37(14) . . . . ?
C2 C3 C4 O5 154.26(11) . . . . ?
C2 C3 O3 C6 -77.64(14) . . . . ?
C3 C4 C5 C6 -1.66(15) . . . . ?
C3 C4 C5 O5 106.05(12) . . . . ?
C3 C4 O5 C5 -96.69(14) . . . . ?
C4 C3 O3 C6 39.46(13) . . . . ?
C4 C5 C6 C7 147.79(12) . . . . ?
C4 C5 C6 N1 -85.28(13) . . . . ?
C4 C5 C6 O3 25.78(14) . . . . ?
C5 C6 C7 C8 -166.97(13) . . . . ?
C5 C6 N1 C1 64.36(17) . . . . ?
C5 C6 N1 O2 -87.54(14) . . . . ?
C5 C6 O3 C3 -40.84(13) . . . . ?
C6 C5 O5 C4 94.69(14) . . . . ?
C6 C7 C8 C9 -58.36(18) . . . . ?
C6 N1 O2 C11 -115.23(13) . . . . ?
C7 C6 N1 C1 -166.75(13) . . . . ?
C7 C6 N1 O2 41.35(17) . . . . ?
C7 C6 O3 C3 -166.42(11) . . . . ?
C7 C8 C9 C10 -48.93(18) . . . . ?
C8 C9 C10 C11 97.59(16) . . . . ?
C9 C10 C11 O2 -67.18(18) . . . . ?
C10 C11 O2 N1 77.68(15) . . . . ?
C12 C2 C3 C4 -176.74(12) . . . . ?
C12 C2 C3 O3 -65.73(14) . . . . ?
C12 C2 C3 O4 52.19(15) . . . . ?
C13 C2 C3 C4 61.66(16) . . . . ?
C13 C2 C3 O3 172.67(12) . . . . ?
C13 C2 C3 O4 -69.40(16) . . . . ?
N1 C1 C2 C3 -25.70(18) . . . . ?
N1 C1 C2 C12 93.30(15) . . . . ?
N1 C1 C2 C13 -147.88(14) . . . . ?
N1 C6 C7 C8 69.47(16) . . . . ?
N1 C6 O3 C3 70.82(13) . . . . ?
O1 C1 C2 C3 160.08(14) . . . . ?
O1 C1 C2 C12 -80.92(17) . . . . ?
O1 C1 C2 C13 37.9(2) . . . . ?
O1 C1 N1 C6 -162.39(14) . . . . ?
O1 C1 N1 O2 -10.6(2) . . . . ?
O3 C3 C4 C5 -22.04(14) . . . . ?
O3 C3 C4 O5 40.85(14) . . . . ?
O3 C6 C7 C8 -48.84(17) . . . . ?
O3 C6 N1 C1 -45.38(17) . . . . ?
O3 C6 N1 O2 162.73(10) . . . . ?
O4 C3 C4 C5 -141.15(13) . . . . ?
O4 C3 C4 O5 -78.26(16) . . . . ?
O4 C3 O3 C6 163.83(12) . . . . ?
O5 C4 C5 C6 -107.71(12) . . . . ?
O5 C5 C6 C7 84.42(16) . . . . ?
O5 C5 C6 N1 -148.65(12) . . . . ?
O5 C5 C6 O3 -37.59(15) . . . . ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
