# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cu_d8v18549_0m
_database_code_depnum_ccdc_archive 'CCDC 1883504'
_audit_update_record             
;
2018-12-06 deposited with the CCDC.
2019-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.9308(8)
_cell_length_b                   6.9507(8)
_cell_length_c                   11.8464(14)
_cell_angle_alpha                84.194(6)
_cell_angle_beta                 79.023(6)
_cell_angle_gamma                64.094(6)
_cell_volume                     503.84(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6254
_cell_measurement_theta_min      7.603
_cell_measurement_theta_max      139.890

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12059
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         70.153
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3664
_reflns_number_gt                3148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_max     0.929
_reflns_Friedel_fraction_full    0.940

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.0358P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.24(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3664
_refine_ls_number_parameters     274
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 1.0583(6) -0.2389(6) 0.7076(4) 0.1018(14) Uani 1 1 d . . . . .
O2 O 0.8202(4) 0.0460(5) 0.6297(2) 0.0655(7) Uani 1 1 d . . . . .
O3 O 0.0086(6) 0.2441(8) 0.8308(4) 0.1004(13) Uani 1 1 d . . . . .
N1 N 0.7828(7) -0.0451(8) 0.9306(3) 0.0759(11) Uani 1 1 d . . . . .
C1 C 0.8821(7) -0.0908(6) 0.7182(4) 0.0654(10) Uani 1 1 d . . . . .
C2 C 0.7040(7) -0.0315(6) 0.8233(3) 0.0591(9) Uani 1 1 d . . . . .
C3 C 0.5609(6) 0.2038(6) 0.7939(3) 0.0526(8) Uani 1 1 d . . . . .
H3 H 0.6196 0.2914 0.8223 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6022(6) 0.2192(6) 0.6626(3) 0.0549(9) Uani 1 1 d . . . . .
C5 C 0.4479(8) 0.1783(7) 0.6067(4) 0.0669(10) Uani 1 1 d . . . . .
H5 H 0.4882 0.1420 0.5296 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2581(8) 0.1908(8) 0.6605(4) 0.0749(12) Uani 1 1 d . . . . .
H6 H 0.1690 0.1672 0.6192 0.090 Uiso 1 1 calc R U . . .
C7 C 0.1824(7) 0.2401(7) 0.7824(4) 0.0708(11) Uani 1 1 d . . . . .
C8 C 0.3204(6) 0.2924(7) 0.8444(4) 0.0623(10) Uani 1 1 d . . . . .
H8A H 0.3066 0.2392 0.9231 0.075 Uiso 1 1 calc R U . . .
H8B H 0.2634 0.4468 0.8471 0.075 Uiso 1 1 calc R U . . .
C9 C 0.5945(9) -0.1823(7) 0.8318(5) 0.0789(13) Uani 1 1 d . . . . .
H9A H 0.6965 -0.3255 0.8474 0.118 Uiso 1 1 calc R U . . .
H9B H 0.5462 -0.1782 0.7604 0.118 Uiso 1 1 calc R U . . .
H9C H 0.4720 -0.1382 0.8928 0.118 Uiso 1 1 calc R U . . .
C10 C 0.6155(8) 0.4253(7) 0.6145(4) 0.0731(12) Uani 1 1 d . . . . .
H10A H 0.7275 0.4411 0.6439 0.110 Uiso 1 1 calc R U . . .
H10B H 0.4786 0.5447 0.6371 0.110 Uiso 1 1 calc R U . . .
H10C H 0.6489 0.4201 0.5321 0.110 Uiso 1 1 calc R U . . .
O4 O 0.6354(7) 0.2236(6) 0.2934(4) 0.1007(13) Uani 1 1 d . . . . .
O5 O 0.3275(5) 0.4797(4) 0.3730(2) 0.0656(8) Uani 1 1 d . . . . .
O6 O 0.1753(8) 1.2372(5) 0.1707(4) 0.0995(13) Uani 1 1 d . . . . .
N2 N 0.4985(10) 0.4463(7) 0.0707(4) 0.0814(12) Uani 1 1 d . . . . .
C11 C 0.4874(7) 0.3973(6) 0.2839(4) 0.0664(10) Uani 1 1 d . . . . .
C12 C 0.4544(7) 0.5470(6) 0.1798(4) 0.0590(9) Uani 1 1 d . . . . .
C13 C 0.2097(6) 0.6941(5) 0.2093(3) 0.0530(8) Uani 1 1 d . . . . .
H13 H 0.1313 0.6252 0.1814 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1600(6) 0.6894(5) 0.3404(3) 0.0554(9) Uani 1 1 d . . . . .
C15 C 0.1868(7) 0.8588(6) 0.3962(4) 0.0646(10) Uani 1 1 d . . . . .
H15 H 0.2045 0.8394 0.4730 0.078 Uiso 1 1 calc R U . . .
C16 C 0.1864(9) 1.0348(7) 0.3411(4) 0.0744(12) Uani 1 1 d . . . . .
H16 H 0.1990 1.1358 0.3814 0.089 Uiso 1 1 calc R U . . .
C17 C 0.1671(8) 1.0756(6) 0.2203(4) 0.0688(11) Uani 1 1 d . . . . .
C18 C 0.1298(7) 0.9211(6) 0.1588(4) 0.0614(10) Uani 1 1 d . . . . .
H18A H 0.2012 0.9150 0.0796 0.074 Uiso 1 1 calc R U . . .
H18B H -0.0250 0.9759 0.1582 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6052(8) 0.6566(8) 0.1732(5) 0.0759(12) Uani 1 1 d . . . . .
H19A H 0.7537 0.5522 0.1580 0.114 Uiso 1 1 calc R U . . .
H19B H 0.5795 0.7236 0.2450 0.114 Uiso 1 1 calc R U . . .
H19C H 0.5772 0.7630 0.1125 0.114 Uiso 1 1 calc R U . . .
C20 C -0.0578(8) 0.6893(8) 0.3909(5) 0.0754(12) Uani 1 1 d . . . . .
H20A H -0.0654 0.5672 0.3644 0.113 Uiso 1 1 calc R U . . .
H20B H -0.1723 0.8177 0.3671 0.113 Uiso 1 1 calc R U . . .
H20C H -0.0738 0.6829 0.4733 0.113 Uiso 1 1 calc R U . . .
H2A H 0.422(11) 0.352(11) 0.080(5) 0.097(18) Uiso 1 1 d . . . . .
H1A H 0.889(15) -0.184(14) 0.939(7) 0.12(2) Uiso 1 1 d . . . . .
H1B H 0.890(14) 0.015(12) 0.920(7) 0.12(2) Uiso 1 1 d . . . . .
H2B H 0.625(15) 0.405(14) 0.049(8) 0.12(3) Uiso 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
O1 C1 1.198(5) . ?
O2 C1 1.342(5) . ?
O2 C4 1.472(5) . ?
O3 C7 1.222(6) . ?
N1 C2 1.455(6) . ?
N1 H1A 0.93(9) . ?
N1 H1B 0.98(8) . ?
C1 C2 1.522(6) . ?
C2 C9 1.526(6) . ?
C2 C3 1.543(5) . ?
C3 C8 1.521(5) . ?
C3 C4 1.529(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.495(6) . ?
C4 C10 1.522(5) . ?
C5 C6 1.318(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.488(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O4 C11 1.207(5) . ?
O5 C11 1.339(5) . ?
O5 C14 1.483(4) . ?
O6 C17 1.233(5) . ?
N2 C12 1.450(6) . ?
N2 H2A 0.99(7) . ?
N2 H2B 0.79(9) . ?
C11 C12 1.515(6) . ?
C12 C19 1.527(7) . ?
C12 C13 1.541(5) . ?
C13 C18 1.525(5) . ?
C13 C14 1.526(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.501(5) . ?
C14 C20 1.515(6) . ?
C15 C16 1.327(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.450(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.491(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C1 O2 C4 111.1(3) . . ?
C2 N1 H1A 108(5) . . ?
C2 N1 H1B 110(5) . . ?
H1A N1 H1B 93(7) . . ?
O1 C1 O2 120.1(4) . . ?
O1 C1 C2 128.2(4) . . ?
O2 C1 C2 111.6(3) . . ?
N1 C2 C1 113.7(4) . . ?
N1 C2 C9 108.8(4) . . ?
C1 C2 C9 108.2(4) . . ?
N1 C2 C3 110.1(3) . . ?
C1 C2 C3 100.8(3) . . ?
C9 C2 C3 115.1(4) . . ?
C8 C3 C4 113.0(3) . . ?
C8 C3 C2 117.1(3) . . ?
C4 C3 C2 104.9(3) . . ?
C8 C3 H3 107.1 . . ?
C4 C3 H3 107.1 . . ?
C2 C3 H3 107.1 . . ?
O2 C4 C5 107.5(3) . . ?
O2 C4 C10 106.2(3) . . ?
C5 C4 C10 110.2(3) . . ?
O2 C4 C3 104.1(3) . . ?
C5 C4 C3 113.9(3) . . ?
C10 C4 C3 114.3(3) . . ?
C6 C5 C4 123.8(4) . . ?
C6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C5 C6 C7 122.4(4) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
O3 C7 C6 121.0(4) . . ?
O3 C7 C8 121.2(5) . . ?
C6 C7 C8 117.8(4) . . ?
C7 C8 C3 116.0(4) . . ?
C7 C8 H8A 108.3 . . ?
C3 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C3 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O5 C14 110.6(3) . . ?
C12 N2 H2A 108(4) . . ?
C12 N2 H2B 106(6) . . ?
H2A N2 H2B 123(7) . . ?
O4 C11 O5 120.0(4) . . ?
O4 C11 C12 128.0(4) . . ?
O5 C11 C12 112.0(3) . . ?
N2 C12 C11 115.3(4) . . ?
N2 C12 C19 108.1(4) . . ?
C11 C12 C19 107.7(4) . . ?
N2 C12 C13 109.6(4) . . ?
C11 C12 C13 100.9(3) . . ?
C19 C12 C13 115.3(3) . . ?
C18 C13 C14 112.6(3) . . ?
C18 C13 C12 117.3(3) . . ?
C14 C13 C12 104.7(3) . . ?
C18 C13 H13 107.3 . . ?
C14 C13 H13 107.3 . . ?
C12 C13 H13 107.3 . . ?
O5 C14 C15 107.2(3) . . ?
O5 C14 C20 106.2(3) . . ?
C15 C14 C20 109.5(3) . . ?
O5 C14 C13 103.7(3) . . ?
C15 C14 C13 114.2(3) . . ?
C20 C14 C13 115.2(4) . . ?
C16 C15 C14 123.1(4) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C17 122.4(4) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
O6 C17 C16 120.7(4) . . ?
O6 C17 C18 121.0(4) . . ?
C16 C17 C18 118.3(3) . . ?
C17 C18 C13 115.5(3) . . ?
C17 C18 H18A 108.4 . . ?
C13 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C13 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 O2 C1 O1 -178.0(5) . . . . ?
C4 O2 C1 C2 2.9(5) . . . . ?
O1 C1 C2 N1 44.6(7) . . . . ?
O2 C1 C2 N1 -136.4(4) . . . . ?
O1 C1 C2 C9 -76.4(7) . . . . ?
O2 C1 C2 C9 102.6(4) . . . . ?
O1 C1 C2 C3 162.4(5) . . . . ?
O2 C1 C2 C3 -18.6(5) . . . . ?
N1 C2 C3 C8 -87.3(4) . . . . ?
C1 C2 C3 C8 152.3(4) . . . . ?
C9 C2 C3 C8 36.1(5) . . . . ?
N1 C2 C3 C4 146.6(3) . . . . ?
C1 C2 C3 C4 26.2(4) . . . . ?
C9 C2 C3 C4 -90.0(4) . . . . ?
C1 O2 C4 C5 -106.6(4) . . . . ?
C1 O2 C4 C10 135.5(4) . . . . ?
C1 O2 C4 C3 14.5(4) . . . . ?
C8 C3 C4 O2 -154.1(3) . . . . ?
C2 C3 C4 O2 -25.5(4) . . . . ?
C8 C3 C4 C5 -37.4(4) . . . . ?
C2 C3 C4 C5 91.2(4) . . . . ?
C8 C3 C4 C10 90.5(4) . . . . ?
C2 C3 C4 C10 -140.9(4) . . . . ?
O2 C4 C5 C6 134.0(5) . . . . ?
C10 C4 C5 C6 -110.7(5) . . . . ?
C3 C4 C5 C6 19.3(6) . . . . ?
C4 C5 C6 C7 -1.9(8) . . . . ?
C5 C6 C7 O3 -177.7(5) . . . . ?
C5 C6 C7 C8 4.3(7) . . . . ?
O3 C7 C8 C3 157.6(5) . . . . ?
C6 C7 C8 C3 -24.4(6) . . . . ?
C4 C3 C8 C7 40.8(5) . . . . ?
C2 C3 C8 C7 -81.2(5) . . . . ?
C14 O5 C11 O4 -177.8(5) . . . . ?
C14 O5 C11 C12 2.8(5) . . . . ?
O4 C11 C12 N2 43.5(8) . . . . ?
O5 C11 C12 N2 -137.2(5) . . . . ?
O4 C11 C12 C19 -77.3(6) . . . . ?
O5 C11 C12 C19 102.0(4) . . . . ?
O4 C11 C12 C13 161.5(5) . . . . ?
O5 C11 C12 C13 -19.2(5) . . . . ?
N2 C12 C13 C18 -85.2(4) . . . . ?
C11 C12 C13 C18 152.8(3) . . . . ?
C19 C12 C13 C18 37.0(5) . . . . ?
N2 C12 C13 C14 149.3(3) . . . . ?
C11 C12 C13 C14 27.2(4) . . . . ?
C19 C12 C13 C14 -88.6(4) . . . . ?
C11 O5 C14 C15 -106.0(4) . . . . ?
C11 O5 C14 C20 137.0(4) . . . . ?
C11 O5 C14 C13 15.2(4) . . . . ?
C18 C13 C14 O5 -154.9(3) . . . . ?
C12 C13 C14 O5 -26.4(4) . . . . ?
C18 C13 C14 C15 -38.6(5) . . . . ?
C12 C13 C14 C15 89.9(4) . . . . ?
C18 C13 C14 C20 89.5(4) . . . . ?
C12 C13 C14 C20 -142.0(3) . . . . ?
O5 C14 C15 C16 134.3(5) . . . . ?
C20 C14 C15 C16 -110.9(5) . . . . ?
C13 C14 C15 C16 19.9(6) . . . . ?
C14 C15 C16 C17 -2.1(8) . . . . ?
C15 C16 C17 O6 -177.3(5) . . . . ?
C15 C16 C17 C18 4.7(7) . . . . ?
O6 C17 C18 C13 156.8(5) . . . . ?
C16 C17 C18 C13 -25.3(6) . . . . ?
C14 C13 C18 C17 41.8(5) . . . . ?
C12 C13 C18 C17 -79.8(5) . . . . ?

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
N1 H1B O3 0.98(8) 2.19(8) 3.075(6) 149(6) 1_655
N2 H2A O6 0.99(7) 2.25(7) 3.165(7) 154(5) 1_545
C18 H18B O4 0.97 2.58 3.318(6) 133.0 1_465
C13 H13 O6 0.98 2.59 3.368(5) 136.2 1_545
C10 H10B O1 0.96 2.64 3.550(6) 159.4 1_465
C8 H8B O1 0.97 2.64 3.380(5) 133.2 1_465
C3 H3 O3 0.98 2.59 3.347(5) 134.1 1_655

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4



