# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_aminjuglona
_database_code_depnum_ccdc_archive 'CCDC 1055524'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-11-03 downloaded from the CCDC.
;

_audit_creation_date             2014-09-26T23:37:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O7'
_chemical_formula_sum            'C19 H21 N O7'
_chemical_formula_weight         375.37
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8376(2)
_cell_length_b                   11.9174(4)
_cell_length_c                   12.2331(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.745(4)
_cell_angle_gamma                90
_cell_volume                     848.13(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4737
_cell_measurement_theta_min      1.7053
_cell_measurement_theta_max      29.357

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4245
_exptl_crystal_size_mid          0.3329
_exptl_crystal_size_min          0.2135
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_F_000             396
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.1181
1 0 1 0.0954
1 -3 2 0.236
0 1 0 0.2256
1 -2 -1 0.2067
-1 0 1 0.1835
-1 2 -3 0.1661
-1 0 -3 0.1395
1 0 4 0.1063
1 3 -2 0.1717

_exptl_special_details           ?


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.91783
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4186
_diffrn_orient_matrix_ub_11      0.0622974
_diffrn_orient_matrix_ub_12      0.011593
_diffrn_orient_matrix_ub_13      0.0510193
_diffrn_orient_matrix_ub_21      0.1035744
_diffrn_orient_matrix_ub_22      0.0020821
_diffrn_orient_matrix_ub_23      -0.0264411
_diffrn_orient_matrix_ub_31      -0.0161436
_diffrn_orient_matrix_ub_32      0.0583218
_diffrn_orient_matrix_ub_33      -0.0091794
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_number            9555
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_number_total             3667
_reflns_number_gt                3075
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0437P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.075
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.2896(3) 0.25695(15) 0.12209(16) 0.0284(4) Uani 1 d . .
O1 O 0.6040(3) 0.25865(14) -0.01014(14) 0.0247(4) Uani 1 d . .
C4 C 0.8403(4) -0.0520(2) 0.10302(19) 0.0185(5) Uani 1 d . .
C9 C 0.5652(4) 0.1076(2) 0.11144(18) 0.0175(5) Uani 1 d . .
O2 O 0.9130(3) -0.14400(14) 0.13236(14) 0.0281(4) Uani 1 d . .
O4 O 1.1792(3) 0.05691(15) -0.30826(13) 0.0217(4) Uani 1 d . .
C10 C 0.6459(4) 0.0032(2) 0.15209(18) 0.0181(5) Uani 1 d . .
N1 N 1.1244(3) -0.04458(18) -0.02655(16) 0.0204(4) Uani 1 d . .
H1A H 1.1655 -0.1082 0.0019 0.024 Uiso 1 calc . .
C3 C 0.9485(4) 0.0099(2) 0.01288(18) 0.0178(5) Uani 1 d . .
O5 O 0.9970(3) -0.17743(14) -0.34877(13) 0.0229(4) Uani 1 d . .
C7 C 0.2749(4) 0.1030(2) 0.2422(2) 0.0272(6) Uani 1 d . .
H7A H 0.1499 0.1358 0.2723 0.033 Uiso 1 calc . .
O7 O 1.5819(3) 0.05149(14) -0.29194(13) 0.0221(4) Uani 1 d . .
C8 C 0.3771(4) 0.1574(2) 0.1572(2) 0.0210(5) Uani 1 d . .
C2 C 0.8665(4) 0.1120(2) -0.02243(19) 0.0198(5) Uani 1 d . .
H2A H 0.9364 0.1485 -0.078 0.024 Uiso 1 calc . .
O6 O 1.2762(3) -0.14429(15) -0.46222(13) 0.0275(4) Uani 1 d . .
C5 C 0.5432(4) -0.0493(2) 0.2363(2) 0.0220(5) Uani 1 d . .
H5A H 0.5976 -0.1183 0.2628 0.026 Uiso 1 calc . .
C11 C 1.2495(4) -0.0009(2) -0.11566(19) 0.0204(5) Uani 1 d . .
H11A H 1.4006 -0.0352 -0.1125 0.024 Uiso 1 calc . .
H11B H 1.27 0.0794 -0.1064 0.024 Uiso 1 calc . .
C6 C 0.3578(5) 0.0018(2) 0.2814(2) 0.0270(6) Uani 1 d . .
H6A H 0.2897 -0.0331 0.3385 0.032 Uiso 1 calc . .
C1 C 0.6779(4) 0.16407(19) 0.02317(18) 0.0187(5) Uani 1 d . .
C13 C 1.1864(4) -0.1367(2) -0.27833(18) 0.0194(5) Uani 1 d . .
H13 H 1.2412 -0.1915 -0.2225 0.023 Uiso 1 calc . .
C18 C 0.8991(5) -0.1881(2) -0.5398(2) 0.0340(7) Uani 1 d . .
H18A H 0.9514 -0.2116 -0.6086 0.051 Uiso 1 calc . .
H18B H 0.8693 -0.1089 -0.542 0.051 Uiso 1 calc . .
H18C H 0.7606 -0.2276 -0.527 0.051 Uiso 1 calc . .
C12 C 1.1219(4) -0.0244(2) -0.22882(19) 0.0197(5) Uani 1 d . .
H12 H 0.9558 -0.0226 -0.2222 0.024 Uiso 1 calc . .
C15 C 1.3800(4) 0.0203(2) -0.35487(19) 0.0198(5) Uani 1 d . .
H15 H 1.3823 0.0496 -0.4296 0.024 Uiso 1 calc . .
C17 C 1.0807(4) -0.2134(2) -0.44900(19) 0.0215(5) Uani 1 d . .
C14 C 1.3699(4) -0.1072(2) -0.35729(19) 0.0207(5) Uani 1 d . .
H14 H 1.5191 -0.1417 -0.3355 0.025 Uiso 1 calc . .
C16 C 1.6076(5) 0.1701(2) -0.2802(2) 0.0269(6) Uani 1 d . .
H16A H 1.748 0.1863 -0.2366 0.04 Uiso 1 calc . .
H16B H 1.48 0.1999 -0.2448 0.04 Uiso 1 calc . .
H16C H 1.612 0.2038 -0.3512 0.04 Uiso 1 calc . .
C19 C 1.1504(5) -0.3357(2) -0.4431(2) 0.0315(6) Uani 1 d . .
H19A H 1.2061 -0.358 -0.5115 0.047 Uiso 1 calc . .
H19B H 1.0198 -0.3808 -0.429 0.047 Uiso 1 calc . .
H19C H 1.2695 -0.346 -0.385 0.047 Uiso 1 calc . .
H3 H 0.376(6) 0.273(3) 0.063(3) 0.045(9) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O3 C8 1.347(3) . ?
O3 H3 0.94(3) . ?
O1 C1 1.262(3) . ?
C4 O2 1.219(3) . ?
C4 C10 1.481(3) . ?
C4 C3 1.508(3) . ?
C9 C8 1.405(3) . ?
C9 C10 1.407(3) . ?
C9 C1 1.473(3) . ?
O4 C15 1.414(3) . ?
O4 C12 1.431(3) . ?
C10 C5 1.384(3) . ?
N1 C3 1.338(3) . ?
N1 C11 1.457(3) . ?
N1 H1A 0.86 . ?
C3 C2 1.365(3) . ?
O5 C17 1.423(3) . ?
O5 C13 1.430(3) . ?
C7 C6 1.372(3) . ?
C7 C8 1.399(4) . ?
C7 H7A 0.93 . ?
O7 C15 1.404(3) . ?
O7 C16 1.427(3) . ?
C2 C1 1.418(3) . ?
C2 H2A 0.93 . ?
O6 C14 1.423(3) . ?
O6 C17 1.427(3) . ?
C5 C6 1.395(4) . ?
C5 H5A 0.93 . ?
C11 C12 1.542(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C6 H6A 0.93 . ?
C13 C12 1.529(3) . ?
C13 C14 1.541(3) . ?
C13 H13 0.98 . ?
C18 C17 1.501(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C12 H12 0.98 . ?
C15 C14 1.520(3) . ?
C15 H15 0.98 . ?
C17 C19 1.514(4) . ?
C14 H14 0.98 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?

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
C8 O3 H3 102(2) . . ?
O2 C4 C10 122.7(2) . . ?
O2 C4 C3 119.9(2) . . ?
C10 C4 C3 117.5(2) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 C1 120.7(2) . . ?
C10 C9 C1 120.4(2) . . ?
C15 O4 C12 108.23(17) . . ?
C5 C10 C9 120.7(2) . . ?
C5 C10 C4 119.7(2) . . ?
C9 C10 C4 119.7(2) . . ?
C3 N1 C11 122.9(2) . . ?
C3 N1 H1A 118.5 . . ?
C11 N1 H1A 118.5 . . ?
N1 C3 C2 125.3(2) . . ?
N1 C3 C4 114.0(2) . . ?
C2 C3 C4 120.7(2) . . ?
C17 O5 C13 108.54(17) . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C15 O7 C16 113.23(18) . . ?
O3 C8 C7 118.1(2) . . ?
O3 C8 C9 122.2(2) . . ?
C7 C8 C9 119.7(2) . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 H2A 119 . . ?
C1 C2 H2A 119 . . ?
C14 O6 C17 109.16(18) . . ?
C10 C5 C6 119.7(2) . . ?
C10 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
N1 C11 C12 111.82(18) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
O1 C1 C2 121.3(2) . . ?
O1 C1 C9 118.9(2) . . ?
C2 C1 C9 119.8(2) . . ?
O5 C13 C12 109.43(19) . . ?
O5 C13 C14 104.05(18) . . ?
C12 C13 C14 104.80(19) . . ?
O5 C13 H13 112.6 . . ?
C12 C13 H13 112.6 . . ?
C14 C13 H13 112.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C12 C13 104.15(18) . . ?
O4 C12 C11 111.33(18) . . ?
C13 C12 C11 113.45(19) . . ?
O4 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C11 C12 H12 109.3 . . ?
O7 C15 O4 112.54(18) . . ?
O7 C15 C14 107.77(18) . . ?
O4 C15 C14 106.51(19) . . ?
O7 C15 H15 110 . . ?
O4 C15 H15 110 . . ?
C14 C15 H15 110 . . ?
O5 C17 O6 104.99(18) . . ?
O5 C17 C18 107.79(19) . . ?
O6 C17 C18 108.8(2) . . ?
O5 C17 C19 111.0(2) . . ?
O6 C17 C19 110.3(2) . . ?
C18 C17 C19 113.5(2) . . ?
O6 C14 C15 109.8(2) . . ?
O6 C14 C13 105.03(18) . . ?
C15 C14 C13 104.10(19) . . ?
O6 C14 H14 112.4 . . ?
C15 C14 H14 112.4 . . ?
C13 C14 H14 112.4 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 C9 C10 C5 -0.5(3) . . . . ?
C1 C9 C10 C5 178.9(2) . . . . ?
C8 C9 C10 C4 178.5(2) . . . . ?
C1 C9 C10 C4 -2.1(3) . . . . ?
O2 C4 C10 C5 1.4(3) . . . . ?
C3 C4 C10 C5 -178.9(2) . . . . ?
O2 C4 C10 C9 -177.6(2) . . . . ?
C3 C4 C10 C9 2.1(3) . . . . ?
C11 N1 C3 C2 -1.2(3) . . . . ?
C11 N1 C3 C4 178.51(18) . . . . ?
O2 C4 C3 N1 -1.0(3) . . . . ?
C10 C4 C3 N1 179.32(19) . . . . ?
O2 C4 C3 C2 178.8(2) . . . . ?
C10 C4 C3 C2 -0.9(3) . . . . ?
C6 C7 C8 O3 -179.7(2) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C10 C9 C8 O3 -179.6(2) . . . . ?
C1 C9 C8 O3 1.0(3) . . . . ?
C10 C9 C8 C7 0.3(3) . . . . ?
C1 C9 C8 C7 -179.0(2) . . . . ?
N1 C3 C2 C1 179.6(2) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C9 C10 C5 C6 0.0(3) . . . . ?
C4 C10 C5 C6 -179.0(2) . . . . ?
C3 N1 C11 C12 -81.3(3) . . . . ?
C8 C7 C6 C5 -0.8(4) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C3 C2 C1 O1 179.9(2) . . . . ?
C3 C2 C1 C9 0.1(3) . . . . ?
C8 C9 C1 O1 0.6(3) . . . . ?
C10 C9 C1 O1 -178.7(2) . . . . ?
C8 C9 C1 C2 -179.6(2) . . . . ?
C10 C9 C1 C2 1.1(3) . . . . ?
C17 O5 C13 C12 133.25(19) . . . . ?
C17 O5 C13 C14 21.7(2) . . . . ?
C15 O4 C12 C13 -35.9(2) . . . . ?
C15 O4 C12 C11 86.7(2) . . . . ?
O5 C13 C12 O4 -87.0(2) . . . . ?
C14 C13 C12 O4 24.1(2) . . . . ?
O5 C13 C12 C11 151.79(18) . . . . ?
C14 C13 C12 C11 -97.2(2) . . . . ?
N1 C11 C12 O4 153.5(2) . . . . ?
N1 C11 C12 C13 -89.4(2) . . . . ?
C16 O7 C15 O4 -60.8(2) . . . . ?
C16 O7 C15 C14 -177.94(19) . . . . ?
C12 O4 C15 O7 -84.8(2) . . . . ?
C12 O4 C15 C14 33.1(2) . . . . ?
C13 O5 C17 O6 -29.7(2) . . . . ?
C13 O5 C17 C18 -145.53(19) . . . . ?
C13 O5 C17 C19 89.5(2) . . . . ?
C14 O6 C17 O5 25.8(2) . . . . ?
C14 O6 C17 C18 140.9(2) . . . . ?
C14 O6 C17 C19 -93.9(2) . . . . ?
C17 O6 C14 C15 -123.7(2) . . . . ?
C17 O6 C14 C13 -12.3(2) . . . . ?
O7 C15 C14 O6 -143.06(18) . . . . ?
O4 C15 C14 O6 96.0(2) . . . . ?
O7 C15 C14 C13 104.9(2) . . . . ?
O4 C15 C14 C13 -16.1(2) . . . . ?
O5 C13 C14 O6 -5.6(2) . . . . ?
C12 C13 C14 O6 -120.51(19) . . . . ?
O5 C13 C14 C15 109.82(19) . . . . ?
C12 C13 C14 C15 -5.1(2) . . . . ?

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 H1A O1 0.86 2.08 2.845(3) 148.3 2_745
C7 H7A O5 0.93 2.59 3.377(3) 143 2_655
C12 H12 O7 0.98 2.44 3.309(3) 147.3 1_455
O3 H3 O1 0.94(3) 1.67(3) 2.545(3) 154(3) .
N1 H1A O1 0.86 2.08 2.845(3) 148.3 2_745
C7 H7A O5 0.93 2.59 3.377(3) 143 2_655
C12 H12 O7 0.98 2.44 3.309(3) 147.3 1_455
O3 H3 O1 0.94(3) 1.67(3) 2.545(3) 154(3) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# 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_triazorib
_database_code_depnum_ccdc_archive 'CCDC 1055525'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-11-03 downloaded from the CCDC.
;

_audit_creation_date             2014-09-26T23:33:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 N3 O7'
_chemical_formula_sum            'C19 H19 N3 O7'
_chemical_formula_weight         401.37
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9539(2)
_cell_length_b                   5.7856(2)
_cell_length_c                   25.9610(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.139(4)
_cell_angle_gamma                90
_cell_volume                     894.10(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3508
_cell_measurement_theta_min      2.3493
_cell_measurement_theta_max      29.4111
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4354
_exptl_crystal_size_mid          0.1852
_exptl_crystal_size_min          0.0663
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.04
0 0 -1 0.0263
0 -2 -1 0.2127
0 2 1 0.2127
4 0 3 0.0847
-4 0 -3 0.0847

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.81004
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4186
_diffrn_orient_matrix_ub_11      -0.0590431
_diffrn_orient_matrix_ub_12      -0.1046955
_diffrn_orient_matrix_ub_13      0.0041237
_diffrn_orient_matrix_ub_21      0.0000415
_diffrn_orient_matrix_ub_22      0.0226038
_diffrn_orient_matrix_ub_23      0.0268524
_diffrn_orient_matrix_ub_31      -0.103506
_diffrn_orient_matrix_ub_32      0.0596455
_diffrn_orient_matrix_ub_33      -0.0029357
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_number            7869
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.951
_reflns_number_total             3770
_reflns_number_gt                3232
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0332P)²+0.2640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3770
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.4(7)
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.5397(3) 0.0926(3) 0.31742(8) 0.0213(5) Uani 1 d . .
O5 O 0.7264(4) -0.3414(4) 0.37896(8) 0.0296(6) Uani 1 d . .
O1 O 0.8215(4) 0.4351(4) 0.07951(10) 0.0312(6) Uani 1 d . .
O7 O 0.1473(4) 0.0538(4) 0.31366(9) 0.0280(5) Uani 1 d . .
O3 O 1.1611(4) 0.3358(4) 0.02270(10) 0.0340(6) Uani 1 d . .
H3 H 1.055 0.4173 0.0334 0.051 Uiso 1 calc . .
O6 O 0.4368(4) -0.1808(5) 0.42204(9) 0.0319(6) Uani 1 d . .
O2 O 0.9794(4) -0.3287(4) 0.19703(9) 0.0339(6) Uani 1 d . .
N3 N 0.5804(5) -0.0161(5) 0.20879(10) 0.0234(6) Uani 1 d . .
N2 N 0.4439(5) 0.1685(5) 0.20113(11) 0.0286(7) Uani 1 d . .
N1 N 0.5271(5) 0.2959(5) 0.16407(11) 0.0279(6) Uani 1 d . .
C14 C 0.3642(5) -0.1858(6) 0.36985(12) 0.0249(7) Uani 1 d . .
H14 H 0.2217 -0.2759 0.3657 0.03 Uiso 1 calc . .
C12 C 0.6225(5) -0.1282(5) 0.29986(12) 0.0214(7) Uani 1 d . .
H12 H 0.79 -0.1217 0.2979 0.026 Uiso 1 calc . .
C8 C 1.1915(5) 0.1528(6) 0.05418(12) 0.0259(7) Uani 1 d . .
C9 C 1.0474(6) 0.1023(5) 0.09499(12) 0.0216(7) Uani 1 d . .
C2 C 0.7186(5) 0.1924(6) 0.14820(12) 0.0225(7) Uani 1 d . .
C10 C 1.0898(5) -0.0972(6) 0.12502(13) 0.0215(7) Uani 1 d . .
C3 C 0.7555(5) -0.0045(6) 0.17628(12) 0.0213(7) Uani 1 d . .
C1 C 0.8604(5) 0.2598(5) 0.10542(12) 0.0231(7) Uani 1 d . .
C13 C 0.5572(5) -0.3029(6) 0.34079(12) 0.0236(7) Uani 1 d . .
H13 H 0.5065 -0.4517 0.3248 0.028 Uiso 1 calc . .
C15 C 0.3405(5) 0.0537(6) 0.34549(13) 0.0245(7) Uani 1 d . .
H15 H 0.3262 0.1733 0.373 0.029 Uiso 1 calc . .
C4 C 0.9446(5) -0.1623(5) 0.16926(13) 0.0239(7) Uani 1 d . .
C7 C 1.3748(6) 0.0096(6) 0.04451(14) 0.0295(8) Uani 1 d . .
H7 H 1.4728 0.0445 0.0171 0.035 Uiso 1 calc . .
C5 C 1.2710(6) -0.2369(6) 0.11485(13) 0.0271(8) Uani 1 d . .
H5 H 1.2988 -0.3705 0.1353 0.033 Uiso 1 calc . .
C11 C 0.5243(5) -0.1911(6) 0.24713(12) 0.0238(7) Uani 1 d . .
H11A H 0.584 -0.3428 0.2363 0.029 Uiso 1 calc . .
H11B H 0.359 -0.2045 0.2493 0.029 Uiso 1 calc . .
C17 C 0.6743(6) -0.2194(6) 0.42506(12) 0.0276(8) Uani 1 d . .
C6 C 1.4129(6) -0.1829(6) 0.07487(13) 0.0278(8) Uani 1 d . .
H6 H 1.5381 -0.2796 0.0683 0.033 Uiso 1 calc . .
C16 C 0.0841(6) 0.2781(6) 0.29552(15) 0.0316(8) Uani 1 d . .
H16A H -0.0512 0.2657 0.2736 0.047 Uiso 1 calc . .
H16B H 0.2067 0.3438 0.2756 0.047 Uiso 1 calc . .
H16C H 0.0536 0.3785 0.325 0.047 Uiso 1 calc . .
C18 C 0.8015(7) 0.0063(7) 0.42847(15) 0.0369(9) Uani 1 d . .
H18A H 0.7635 0.0862 0.4604 0.055 Uiso 1 calc . .
H18B H 0.7601 0.1038 0.3989 0.055 Uiso 1 calc . .
H18C H 0.9633 -0.0246 0.4283 0.055 Uiso 1 calc . .
C19 C 0.7247(7) -0.3755(8) 0.47038(14) 0.0449(11) Uani 1 d . .
H19A H 0.6895 -0.2947 0.5024 0.067 Uiso 1 calc . .
H19B H 0.8842 -0.4173 0.4708 0.067 Uiso 1 calc . .
H19C H 0.6332 -0.5158 0.4674 0.067 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O4 C15 1.422(4) . ?
O4 C12 1.447(3) . ?
O5 C13 1.417(4) . ?
O5 C17 1.429(4) . ?
O1 C1 1.236(4) . ?
O7 C15 1.403(4) . ?
O7 C16 1.428(4) . ?
O3 C8 1.347(4) . ?
O3 H3 0.84 . ?
O6 C14 1.414(4) . ?
O6 C17 1.432(4) . ?
O2 C4 1.218(4) . ?
N3 N2 1.354(4) . ?
N3 C3 1.356(4) . ?
N3 C11 1.463(4) . ?
N2 N1 1.317(4) . ?
N1 C2 1.359(4) . ?
C14 C15 1.529(5) . ?
C14 C13 1.544(4) . ?
C14 H14 1 . ?
C12 C11 1.522(4) . ?
C12 C13 1.523(4) . ?
C12 H12 1 . ?
C8 C7 1.397(5) . ?
C8 C9 1.407(4) . ?
C9 C10 1.413(4) . ?
C9 C1 1.468(4) . ?
C2 C3 1.368(5) . ?
C2 C1 1.462(4) . ?
C10 C5 1.377(4) . ?
C10 C4 1.500(4) . ?
C3 C4 1.463(4) . ?
C13 H13 1 . ?
C15 H15 1 . ?
C7 C6 1.381(5) . ?
C7 H7 0.95 . ?
C5 C6 1.387(5) . ?
C5 H5 0.95 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C17 C19 1.509(5) . ?
C17 C18 1.511(5) . ?
C6 H6 0.95 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?

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
C15 O4 C12 108.3(2) . . ?
C13 O5 C17 110.2(2) . . ?
C15 O7 C16 113.7(2) . . ?
C8 O3 H3 109.5 . . ?
C14 O6 C17 109.4(2) . . ?
N2 N3 C3 109.7(3) . . ?
N2 N3 C11 120.1(3) . . ?
C3 N3 C11 130.3(3) . . ?
N1 N2 N3 108.4(3) . . ?
N2 N1 C2 107.7(3) . . ?
O6 C14 C15 113.7(3) . . ?
O6 C14 C13 105.1(3) . . ?
C15 C14 C13 105.0(2) . . ?
O6 C14 H14 110.9 . . ?
C15 C14 H14 110.9 . . ?
C13 C14 H14 110.9 . . ?
O4 C12 C11 111.6(3) . . ?
O4 C12 C13 105.8(2) . . ?
C11 C12 C13 111.7(3) . . ?
O4 C12 H12 109.2 . . ?
C11 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
O3 C8 C7 116.9(3) . . ?
O3 C8 C9 122.9(3) . . ?
C7 C8 C9 120.1(3) . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 C1 119.1(3) . . ?
C10 C9 C1 122.2(3) . . ?
N1 C2 C3 109.4(3) . . ?
N1 C2 C1 127.9(3) . . ?
C3 C2 C1 122.5(3) . . ?
C5 C10 C9 120.4(3) . . ?
C5 C10 C4 117.7(3) . . ?
C9 C10 C4 121.9(3) . . ?
N3 C3 C2 104.8(3) . . ?
N3 C3 C4 130.5(3) . . ?
C2 C3 C4 124.7(3) . . ?
O1 C1 C2 121.8(3) . . ?
O1 C1 C9 122.9(3) . . ?
C2 C1 C9 115.2(3) . . ?
O5 C13 C12 113.9(3) . . ?
O5 C13 C14 104.7(2) . . ?
C12 C13 C14 104.6(3) . . ?
O5 C13 H13 111.1 . . ?
C12 C13 H13 111.1 . . ?
C14 C13 H13 111.1 . . ?
O7 C15 O4 112.4(3) . . ?
O7 C15 C14 108.2(3) . . ?
O4 C15 C14 106.5(2) . . ?
O7 C15 H15 109.9 . . ?
O4 C15 H15 109.9 . . ?
C14 C15 H15 109.9 . . ?
O2 C4 C3 122.8(3) . . ?
O2 C4 C10 123.9(3) . . ?
C3 C4 C10 113.3(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C10 C5 C6 120.2(3) . . ?
C10 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N3 C11 C12 111.0(3) . . ?
N3 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
O5 C17 O6 105.2(3) . . ?
O5 C17 C19 108.3(3) . . ?
O6 C17 C19 108.5(3) . . ?
O5 C17 C18 111.0(3) . . ?
O6 C17 C18 111.2(3) . . ?
C19 C17 C18 112.3(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C3 N3 N2 N1 0.7(4) . . . . ?
C11 N3 N2 N1 -178.3(3) . . . . ?
N3 N2 N1 C2 -0.3(4) . . . . ?
C17 O6 C14 C15 -97.6(3) . . . . ?
C17 O6 C14 C13 16.8(3) . . . . ?
C15 O4 C12 C11 89.9(3) . . . . ?
C15 O4 C12 C13 -31.8(3) . . . . ?
O3 C8 C9 C10 178.3(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
O3 C8 C9 C1 -2.6(5) . . . . ?
C7 C8 C9 C1 178.0(3) . . . . ?
N2 N1 C2 C3 -0.1(4) . . . . ?
N2 N1 C2 C1 175.0(3) . . . . ?
C8 C9 C10 C5 1.0(5) . . . . ?
C1 C9 C10 C5 -178.1(3) . . . . ?
C8 C9 C10 C4 179.8(3) . . . . ?
C1 C9 C10 C4 0.7(5) . . . . ?
N2 N3 C3 C2 -0.7(3) . . . . ?
C11 N3 C3 C2 178.1(3) . . . . ?
N2 N3 C3 C4 -179.1(3) . . . . ?
C11 N3 C3 C4 -0.3(6) . . . . ?
N1 C2 C3 N3 0.5(4) . . . . ?
C1 C2 C3 N3 -174.9(3) . . . . ?
N1 C2 C3 C4 179.1(3) . . . . ?
C1 C2 C3 C4 3.6(5) . . . . ?
N1 C2 C1 O1 3.5(5) . . . . ?
C3 C2 C1 O1 178.0(3) . . . . ?
N1 C2 C1 C9 -175.2(3) . . . . ?
C3 C2 C1 C9 -0.6(5) . . . . ?
C8 C9 C1 O1 0.8(5) . . . . ?
C10 C9 C1 O1 179.9(3) . . . . ?
C8 C9 C1 C2 179.5(3) . . . . ?
C10 C9 C1 C2 -1.4(4) . . . . ?
C17 O5 C13 C12 102.1(3) . . . . ?
C17 O5 C13 C14 -11.6(3) . . . . ?
O4 C12 C13 O5 -93.3(3) . . . . ?
C11 C12 C13 O5 145.1(3) . . . . ?
O4 C12 C13 C14 20.4(3) . . . . ?
C11 C12 C13 C14 -101.2(3) . . . . ?
O6 C14 C13 O5 -3.2(3) . . . . ?
C15 C14 C13 O5 117.0(3) . . . . ?
O6 C14 C13 C12 -123.2(3) . . . . ?
C15 C14 C13 C12 -3.0(3) . . . . ?
C16 O7 C15 O4 -72.9(3) . . . . ?
C16 O7 C15 C14 169.8(3) . . . . ?
C12 O4 C15 O7 -88.4(3) . . . . ?
C12 O4 C15 C14 29.9(3) . . . . ?
O6 C14 C15 O7 -140.4(3) . . . . ?
C13 C14 C15 O7 105.2(3) . . . . ?
O6 C14 C15 O4 98.6(3) . . . . ?
C13 C14 C15 O4 -15.8(3) . . . . ?
N3 C3 C4 O2 -6.4(6) . . . . ?
C2 C3 C4 O2 175.5(3) . . . . ?
N3 C3 C4 C10 174.0(3) . . . . ?
C2 C3 C4 C10 -4.1(5) . . . . ?
C5 C10 C4 O2 1.2(5) . . . . ?
C9 C10 C4 O2 -177.7(3) . . . . ?
C5 C10 C4 C3 -179.2(3) . . . . ?
C9 C10 C4 C3 1.9(4) . . . . ?
O3 C8 C7 C6 -178.9(3) . . . . ?
C9 C8 C7 C6 0.5(5) . . . . ?
C9 C10 C5 C6 -0.2(5) . . . . ?
C4 C10 C5 C6 -179.0(3) . . . . ?
N2 N3 C11 C12 -88.8(3) . . . . ?
C3 N3 C11 C12 92.4(4) . . . . ?
O4 C12 C11 N3 59.2(3) . . . . ?
C13 C12 C11 N3 177.5(2) . . . . ?
C13 O5 C17 O6 21.9(3) . . . . ?
C13 O5 C17 C19 137.7(3) . . . . ?
C13 O5 C17 C18 -98.5(3) . . . . ?
C14 O6 C17 O5 -24.0(3) . . . . ?
C14 O6 C17 C19 -139.7(3) . . . . ?
C14 O6 C17 C18 96.3(3) . . . . ?
C8 C7 C6 C5 0.3(5) . . . . ?
C10 C5 C6 C7 -0.4(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
O3 H3 O1 0.84 1.86 2.591(3) 145.4 .

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# END of CIF
