# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_smi9
_database_code_depnum_ccdc_archive 'CCDC 1449943'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;
_audit_creation_date             2015-06-19
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H20 N O8 P'
_chemical_formula_sum            'C16 H20 N O8 P'
_chemical_formula_weight         385.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H20 N1 o8 p1'
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'
P P 0.1023 0.0942 '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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.8135(7)
_cell_length_b                   9.3935(9)
_cell_length_c                   11.2015(10)
_cell_angle_alpha                78.735(8)
_cell_angle_beta                 81.657(7)
_cell_angle_gamma                85.426(7)
_cell_volume                     898.60(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.9770
_cell_measurement_theta_min      3.1290
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8555
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751 -178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751    0.0000  120.0000 122

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126  -99.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega  -23.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126  -99.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2126 -178.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.2751  -77.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0625685000
_diffrn_orient_matrix_UB_12      -0.0136386000
_diffrn_orient_matrix_UB_13      0.0347037000
_diffrn_orient_matrix_UB_21      -0.0397337000
_diffrn_orient_matrix_UB_22      -0.0563337000
_diffrn_orient_matrix_UB_23      0.0412339000
_diffrn_orient_matrix_UB_31      0.0337819000
_diffrn_orient_matrix_UB_32      -0.0508446000
_diffrn_orient_matrix_UB_33      -0.0365876000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3510
_reflns_number_total             4127
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.74537(4) 0.23846(4) 0.11955(3) 0.01423(11) Uani 1 1 d . . .
O4 O 0.57684(12) 0.30204(12) 0.15204(10) 0.0190(2) Uani 1 1 d . . .
O7 O 1.01530(12) 0.24159(12) 0.44973(10) 0.0165(2) Uani 1 1 d . . .
O2 O 0.97811(12) -0.01861(12) 0.27442(10) 0.0169(2) Uani 1 1 d . . .
O3 O 0.75699(14) 0.11102(13) 0.06061(10) 0.0225(3) Uani 1 1 d . . .
O6 O 1.02995(13) 0.47526(12) 0.35278(10) 0.0189(2) Uani 1 1 d . . .
O5 O 0.83339(13) 0.37464(12) 0.04919(10) 0.0185(2) Uani 1 1 d . . .
O1 O 1.09755(12) 0.18890(13) 0.19482(10) 0.0194(2) Uani 1 1 d . . .
O8 O 0.33775(13) 0.34687(12) 0.84749(10) 0.0191(2) Uani 1 1 d . . .
N1 N 0.71573(14) 0.12838(14) 0.36673(11) 0.0128(3) Uani 1 1 d . . .
C4 C 0.61372(16) 0.26394(16) 0.53336(13) 0.0124(3) Uani 1 1 d . . .
C7 C 0.42763(17) 0.31182(17) 0.74681(13) 0.0140(3) Uani 1 1 d . . .
C1 C 0.82796(16) 0.20264(16) 0.26367(13) 0.0121(3) Uani 1 1 d . . .
C11 C 0.98473(17) 0.12463(16) 0.24129(13) 0.0137(3) Uani 1 1 d . . .
C2 C 0.82019(17) 0.33594(16) 0.33090(13) 0.0129(3) Uani 1 1 d . . .
H2 H 0.7715 0.4244 0.2871 0.015 Uiso 1 1 calc R . .
C3 C 0.70772(16) 0.24045(16) 0.42034(13) 0.0121(3) Uani 1 1 d . . .
C15 C 0.96657(17) 0.36225(16) 0.37737(13) 0.0132(3) Uani 1 1 d . . .
C6 C 0.53934(18) 0.40934(17) 0.69011(14) 0.0164(3) Uani 1 1 d . . .
H6 H 0.5517 0.4902 0.7235 0.020 Uiso 1 1 calc R . .
C9 C 0.50404(17) 0.16605(17) 0.59296(13) 0.0146(3) Uani 1 1 d . . .
H9 H 0.4933 0.0839 0.5608 0.017 Uiso 1 1 calc R . .
C16 C 1.16188(18) 0.24699(19) 0.49240(15) 0.0197(3) Uani 1 1 d . . .
H16A H 1.2376 0.2787 0.4235 0.029 Uiso 1 1 calc R . .
H16B H 1.1927 0.1520 0.5338 0.029 Uiso 1 1 calc R . .
H16C H 1.1525 0.3139 0.5482 0.029 Uiso 1 1 calc R . .
C12 C 1.12211(19) -0.10054(19) 0.24774(16) 0.0227(4) Uani 1 1 d . . .
H12A H 1.1523 -0.0854 0.1605 0.034 Uiso 1 1 calc R . .
H12B H 1.1089 -0.2021 0.2789 0.034 Uiso 1 1 calc R . .
H12C H 1.2002 -0.0681 0.2862 0.034 Uiso 1 1 calc R . .
C5 C 0.63156(17) 0.38575(17) 0.58436(14) 0.0157(3) Uani 1 1 d . . .
H5 H 0.7059 0.4509 0.5467 0.019 Uiso 1 1 calc R . .
C8 C 0.41077(17) 0.18815(17) 0.69887(14) 0.0153(3) Uani 1 1 d . . .
H8 H 0.3380 0.1218 0.7376 0.018 Uiso 1 1 calc R . .
C13 C 0.4491(2) 0.2077(2) 0.17158(19) 0.0312(4) Uani 1 1 d . . .
H13A H 0.4535 0.1598 0.1028 0.047 Uiso 1 1 calc R . .
H13B H 0.3541 0.2646 0.1798 0.047 Uiso 1 1 calc R . .
H13C H 0.4553 0.1363 0.2450 0.047 Uiso 1 1 calc R . .
C10 C 0.2068(2) 0.2613(2) 0.89562(16) 0.0243(4) Uani 1 1 d . . .
H10A H 0.1446 0.2627 0.8317 0.036 Uiso 1 1 calc R . .
H10B H 0.1473 0.3010 0.9614 0.036 Uiso 1 1 calc R . .
H10C H 0.2409 0.1629 0.9259 0.036 Uiso 1 1 calc R . .
C14 C 0.7951(2) 0.44568(19) -0.07064(15) 0.0271(4) Uani 1 1 d . . .
H14A H 0.7986 0.3749 -0.1224 0.041 Uiso 1 1 calc R . .
H14B H 0.8676 0.5180 -0.1070 0.041 Uiso 1 1 calc R . .
H14C H 0.6936 0.4912 -0.0617 0.041 Uiso 1 1 calc R . .


_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
P1 O4 1.5754(12) . ?
P1 O3 1.4659(12) . ?
P1 O5 1.5641(12) . ?
P1 C1 1.8273(15) . ?
O4 C13 1.454(2) . ?
O7 C15 1.3381(18) . ?
O7 C16 1.4488(18) . ?
O2 C11 1.3277(18) . ?
O2 C12 1.4548(18) . ?
O6 C15 1.2044(18) . ?
O5 C14 1.4515(19) . ?
O1 C11 1.2029(18) . ?
O8 C7 1.3609(17) . ?
O8 C10 1.4381(19) . ?
N1 C1 1.5039(18) . ?
N1 C3 1.3025(19) . ?
C4 C3 1.454(2) . ?
C4 C9 1.393(2) . ?
C4 C5 1.404(2) . ?
C7 C6 1.395(2) . ?
C7 C8 1.398(2) . ?
C1 C11 1.523(2) . ?
C1 C2 1.575(2) . ?
C1 C3 1.993(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.514(2) . ?
C2 C15 1.514(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 P1 C1 105.41(6) . . ?
O3 P1 O4 114.98(7) . . ?
O3 P1 O5 117.59(7) . . ?
O3 P1 C1 112.86(7) . . ?
O5 P1 O4 103.61(6) . . ?
O5 P1 C1 100.70(6) . . ?
C13 O4 P1 119.56(11) . . ?
C15 O7 C16 116.13(12) . . ?
C11 O2 C12 114.85(12) . . ?
C14 O5 P1 119.15(11) . . ?
C7 O8 C10 116.88(12) . . ?
C3 N1 C1 90.21(11) . . ?
C9 C4 C3 120.58(13) . . ?
C9 C4 C5 118.76(13) . . ?
C5 C4 C3 120.66(13) . . ?
O8 C7 C6 115.97(13) . . ?
O8 C7 C8 123.64(14) . . ?
C6 C7 C8 120.38(13) . . ?
P1 C1 C3 121.91(9) . . ?
N1 C1 P1 110.42(9) . . ?
N1 C1 C11 116.66(12) . . ?
N1 C1 C2 89.30(10) . . ?
N1 C1 C3 40.80(7) . . ?
C11 C1 P1 107.80(9) . . ?
C11 C1 C2 116.63(12) . . ?
C11 C1 C3 129.77(11) . . ?
C2 C1 P1 115.26(10) . . ?
C2 C1 C3 48.50(8) . . ?
O2 C11 C1 111.98(12) . . ?
O1 C11 O2 125.81(14) . . ?
O1 C11 C1 122.16(14) . . ?
C1 C2 H2 113.4 . . ?
C3 C2 C1 80.34(10) . . ?
C3 C2 H2 113.4 . . ?
C15 C2 C1 115.86(12) . . ?
C15 C2 H2 113.4 . . ?
C15 C2 C3 116.44(12) . . ?
N1 C3 C4 128.60(14) . . ?
N1 C3 C1 48.98(8) . . ?
N1 C3 C2 100.12(12) . . ?
C4 C3 C1 177.07(12) . . ?
C4 C3 C2 131.27(13) . . ?
C2 C3 C1 51.15(8) . . ?
O7 C15 C2 110.09(12) . . ?
O6 C15 O7 124.94(14) . . ?
O6 C15 C2 124.97(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 119.98(14) . . ?
C5 C6 H6 120.0 . . ?
C4 C9 H9 119.2 . . ?
C8 C9 C4 121.55(14) . . ?
C8 C9 H9 119.2 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.38(14) . . ?
C6 C5 H5 119.8 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.92(14) . . ?
C9 C8 H8 120.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C10 H10A 109.5 . . ?
O8 C10 H10B 109.5 . . ?
O8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
P1 C1 C11 O2 -96.22(12) . . . . ?
P1 C1 C11 O1 81.35(15) . . . . ?
P1 C1 C2 C3 111.27(11) . . . . ?
P1 C1 C2 C15 -133.92(11) . . . . ?
P1 C1 C3 N1 84.71(12) . . . . ?
P1 C1 C3 C4 50(2) . . . . ?
P1 C1 C3 C2 -96.92(12) . . . . ?
O4 P1 O5 C14 -67.56(13) . . . . ?
O4 P1 C1 N1 45.06(11) . . . . ?
O4 P1 C1 C11 173.56(10) . . . . ?
O4 P1 C1 C2 -54.22(11) . . . . ?
O4 P1 C1 C3 1.09(12) . . . . ?
O3 P1 O4 C13 25.25(14) . . . . ?
O3 P1 O5 C14 60.52(14) . . . . ?
O3 P1 C1 N1 -81.21(11) . . . . ?
O3 P1 C1 C11 47.29(12) . . . . ?
O3 P1 C1 C2 179.51(10) . . . . ?
O3 P1 C1 C3 -125.18(10) . . . . ?
O5 P1 O4 C13 154.93(12) . . . . ?
O5 P1 C1 N1 152.55(10) . . . . ?
O5 P1 C1 C11 -78.95(11) . . . . ?
O5 P1 C1 C2 53.27(11) . . . . ?
O5 P1 C1 C3 108.58(10) . . . . ?
O8 C7 C6 C5 -177.30(13) . . . . ?
O8 C7 C8 C9 177.25(14) . . . . ?
N1 C1 C11 O2 28.63(17) . . . . ?
N1 C1 C11 O1 -153.81(14) . . . . ?
N1 C1 C2 C3 -1.06(10) . . . . ?
N1 C1 C2 C15 113.74(13) . . . . ?
N1 C1 C3 C4 -35(2) . . . . ?
N1 C1 C3 C2 178.37(15) . . . . ?
C4 C9 C8 C7 0.0(2) . . . . ?
C7 C6 C5 C4 0.0(2) . . . . ?
C1 P1 O4 C13 -99.71(13) . . . . ?
C1 P1 O5 C14 -176.47(12) . . . . ?
C1 N1 C3 C4 177.85(15) . . . . ?
C1 N1 C3 C2 -1.29(12) . . . . ?
C1 C2 C3 N1 1.25(11) . . . . ?
C1 C2 C3 C4 -177.85(15) . . . . ?
C1 C2 C15 O7 -54.48(16) . . . . ?
C1 C2 C15 O6 125.50(16) . . . . ?
C11 C1 C2 C3 -120.79(13) . . . . ?
C11 C1 C2 C15 -5.99(18) . . . . ?
C11 C1 C3 N1 -85.95(16) . . . . ?
C11 C1 C3 C4 -121(2) . . . . ?
C11 C1 C3 C2 92.42(16) . . . . ?
C2 C1 C11 O2 132.30(13) . . . . ?
C2 C1 C11 O1 -50.13(19) . . . . ?
C2 C1 C3 N1 -178.37(15) . . . . ?
C2 C1 C3 C4 147(2) . . . . ?
C3 N1 C1 P1 -115.58(10) . . . . ?
C3 N1 C1 C11 120.91(13) . . . . ?
C3 N1 C1 C2 1.22(11) . . . . ?
C3 C4 C9 C8 -178.37(14) . . . . ?
C3 C4 C5 C6 178.41(14) . . . . ?
C3 C1 C11 O2 75.46(17) . . . . ?
C3 C1 C11 O1 -106.97(17) . . . . ?
C3 C1 C2 C15 114.80(14) . . . . ?
C3 C2 C15 O7 37.40(17) . . . . ?
C3 C2 C15 O6 -142.62(15) . . . . ?
C15 C2 C3 N1 -112.93(13) . . . . ?
C15 C2 C3 C4 68.0(2) . . . . ?
C15 C2 C3 C1 -114.18(14) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C9 C4 C3 N1 -6.7(2) . . . . ?
C9 C4 C3 C1 27(3) . . . . ?
C9 C4 C3 C2 172.18(14) . . . . ?
C9 C4 C5 C6 -1.5(2) . . . . ?
C16 O7 C15 O6 -5.1(2) . . . . ?
C16 O7 C15 C2 174.85(12) . . . . ?
C12 O2 C11 O1 -1.5(2) . . . . ?
C12 O2 C11 C1 175.99(12) . . . . ?
C5 C4 C3 N1 173.42(14) . . . . ?
C5 C4 C3 C1 -153(2) . . . . ?
C5 C4 C3 C2 -7.7(2) . . . . ?
C5 C4 C9 C8 1.5(2) . . . . ?
C8 C7 C6 C5 1.5(2) . . . . ?
C10 O8 C7 C6 170.33(14) . . . . ?
C10 O8 C7 C8 -8.5(2) . . . . ?

####################################################################### 
# 
# 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_smi4
_database_code_depnum_ccdc_archive 'CCDC 1449965'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H15 N O6'
_chemical_formula_sum            'C15 H15 N O6'
_chemical_formula_weight         305.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H15 N1 O6'
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      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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.47048(18)
_cell_length_b                   8.60587(17)
_cell_length_c                   18.2016(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1319(17)
_cell_angle_gamma                90.00
_cell_volume                     1468.55(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9230
_cell_measurement_theta_min      4.9090
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8087
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.91
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega   89.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega  122.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   73.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   99.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega  103.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   59.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  116.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 17 omega  109.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 18 omega   51.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 20 omega   43.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 21 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1033986000
_diffrn_orient_matrix_UB_12      -0.0083330000
_diffrn_orient_matrix_UB_13      -0.0733270000
_diffrn_orient_matrix_UB_21      -0.1197007000
_diffrn_orient_matrix_UB_22      -0.0561086000
_diffrn_orient_matrix_UB_23      0.0427402000
_diffrn_orient_matrix_UB_31      -0.0445605000
_diffrn_orient_matrix_UB_32      0.1697211000
_diffrn_orient_matrix_UB_33      0.0104831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2555
_reflns_number_total             2800
_reflns_odcompleteness_completeness 94.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+0.5769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.16280(9) 0.51443(9) 0.14445(4) 0.0199(2) Uani 1 1 d . . .
O3 O 0.36904(9) 0.15102(10) 0.12164(5) 0.0226(2) Uani 1 1 d . . .
O6 O -0.04703(9) 0.00131(10) 0.10002(5) 0.0202(2) Uani 1 1 d . . .
O5 O -0.14599(9) 0.20254(11) 0.15314(5) 0.0259(2) Uani 1 1 d . . .
O4 O 0.43257(8) 0.22152(10) 0.24100(5) 0.01955(19) Uani 1 1 d . . .
O1 O 0.08195(10) 0.32427(10) 0.06530(5) 0.0257(2) Uani 1 1 d . . .
N1 N 0.17469(10) 0.32133(11) 0.26387(5) 0.0135(2) Uani 1 1 d . . .
C9 C 0.03851(13) 0.27808(14) 0.39977(6) 0.0187(2) Uani 1 1 d . . .
H9 H 0.1000 0.3624 0.4001 0.022 Uiso 1 1 calc R . .
C1 C 0.19219(11) 0.25939(13) 0.18886(6) 0.0126(2) Uani 1 1 d . . .
C7 C -0.12356(14) 0.12419(16) 0.45972(7) 0.0246(3) Uani 1 1 d . . .
H7 H -0.1701 0.1058 0.5006 0.030 Uiso 1 1 calc R . .
C8 C -0.03071(14) 0.24921(15) 0.46048(7) 0.0225(3) Uani 1 1 d . . .
H8 H -0.0150 0.3137 0.5018 0.027 Uiso 1 1 calc R . .
C2 C 0.09019(11) 0.12021(13) 0.20214(6) 0.0129(2) Uani 1 1 d . . .
H2 H 0.1390 0.0197 0.2088 0.016 Uiso 1 1 calc R . .
C5 C -0.07746(12) 0.05402(14) 0.33775(7) 0.0183(2) Uani 1 1 d . . .
H5 H -0.0926 -0.0116 0.2968 0.022 Uiso 1 1 calc R . .
C10 C 0.13749(11) 0.36810(13) 0.12515(6) 0.0143(2) Uani 1 1 d . . .
C11 C 0.10856(14) 0.62901(14) 0.08876(7) 0.0235(3) Uani 1 1 d . . .
H11A H 0.1569 0.6178 0.0461 0.035 Uiso 1 1 calc R . .
H11B H 0.1249 0.7315 0.1090 0.035 Uiso 1 1 calc R . .
H11C H 0.0081 0.6133 0.0744 0.035 Uiso 1 1 calc R . .
C6 C -0.14763(13) 0.02650(15) 0.39872(7) 0.0233(3) Uani 1 1 d . . .
H6 H -0.2102 -0.0568 0.3985 0.028 Uiso 1 1 calc R . .
C13 C 0.57323(13) 0.15458(17) 0.23965(8) 0.0286(3) Uani 1 1 d . . .
H13A H 0.6111 0.1911 0.1966 0.043 Uiso 1 1 calc R . .
H13B H 0.5659 0.0433 0.2379 0.043 Uiso 1 1 calc R . .
H13C H 0.6355 0.1851 0.2835 0.043 Uiso 1 1 calc R . .
C4 C 0.01547(12) 0.17984(13) 0.33796(6) 0.0150(2) Uani 1 1 d . . .
C3 C 0.08854(11) 0.20871(13) 0.27379(6) 0.0133(2) Uani 1 1 d . . .
C12 C 0.34187(12) 0.20446(13) 0.17900(6) 0.0148(2) Uani 1 1 d . . .
C15 C -0.16933(15) -0.00157(17) 0.04214(7) 0.0286(3) Uani 1 1 d . . .
H15A H -0.1605 -0.0874 0.0094 0.043 Uiso 1 1 calc R . .
H15B H -0.1733 0.0938 0.0146 0.043 Uiso 1 1 calc R . .
H15C H -0.2550 -0.0130 0.0642 0.043 Uiso 1 1 calc R . .
C14 C -0.04835(12) 0.11412(13) 0.14984(6) 0.0156(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
O2 C10 1.3202(14) . ?
O2 C11 1.4548(14) . ?
O3 C12 1.2015(14) . ?
O6 C15 1.4515(15) . ?
O6 C14 1.3298(14) . ?
O5 C14 1.2055(15) . ?
O4 C13 1.4548(14) . ?
O4 C12 1.3261(14) . ?
O1 C10 1.2014(14) . ?
N1 C1 1.4966(13) . ?
N1 C3 1.2959(15) . ?
C9 H9 0.9300 . ?
C9 C8 1.3847(17) . ?
C9 C4 1.3995(17) . ?
C1 C2 1.5787(15) . ?
C1 C10 1.5227(15) . ?
C1 C3 1.9931(16) . ?
C1 C12 1.5287(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.3883(19) . ?
C7 C6 1.3856(19) . ?
C8 H8 0.9300 . ?
C2 H2 0.9800 . ?
C2 C3 1.5121(15) . ?
C2 C14 1.5090(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3921(17) . ?
C5 C4 1.3950(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C6 H6 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 C3 1.4607(15) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C10 O2 C11 115.35(9) . . ?
C14 O6 C15 115.09(10) . . ?
C12 O4 C13 115.23(10) . . ?
C3 N1 C1 90.79(9) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C4 119.70(11) . . ?
C4 C9 H9 120.1 . . ?
N1 C1 C2 88.93(8) . . ?
N1 C1 C10 113.97(9) . . ?
N1 C1 C3 40.55(6) . . ?
N1 C1 C12 116.20(9) . . ?
C2 C1 C3 48.40(6) . . ?
C10 C1 C2 115.67(9) . . ?
C10 C1 C3 124.98(8) . . ?
C10 C1 C12 108.77(9) . . ?
C12 C1 C2 112.40(9) . . ?
C12 C1 C3 126.16(8) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.69(11) . . ?
C9 C8 C7 120.11(12) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C1 C2 H2 113.6 . . ?
C3 C2 C1 80.28(8) . . ?
C3 C2 H2 113.6 . . ?
C14 C2 C1 115.21(9) . . ?
C14 C2 H2 113.6 . . ?
C14 C2 C3 116.57(9) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.13(11) . . ?
C4 C5 H5 119.9 . . ?
O2 C10 C1 110.73(9) . . ?
O1 C10 O2 125.49(10) . . ?
O1 C10 C1 123.76(10) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C6 C5 119.51(12) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C4 C3 120.16(10) . . ?
C5 C4 C9 119.85(11) . . ?
C5 C4 C3 119.99(10) . . ?
N1 C3 C1 48.66(6) . . ?
N1 C3 C2 99.97(9) . . ?
N1 C3 C4 128.12(10) . . ?
C2 C3 C1 51.32(6) . . ?
C4 C3 C1 176.77(9) . . ?
C4 C3 C2 131.90(10) . . ?
O3 C12 O4 126.10(11) . . ?
O3 C12 C1 122.44(10) . . ?
O4 C12 C1 111.45(9) . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C14 C2 111.37(9) . . ?
O5 C14 O6 125.17(11) . . ?
O5 C14 C2 123.46(10) . . ?

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
N1 C1 C2 C3 1.15(7) . . . . ?
N1 C1 C2 C14 116.04(9) . . . . ?
N1 C1 C10 O2 36.49(13) . . . . ?
N1 C1 C10 O1 -145.01(11) . . . . ?
N1 C1 C3 C2 -178.23(11) . . . . ?
N1 C1 C3 C4 6.1(16) . . . . ?
N1 C1 C12 O3 179.24(10) . . . . ?
N1 C1 C12 O4 0.28(13) . . . . ?
C9 C4 C3 N1 -2.00(17) . . . . ?
C9 C4 C3 C1 -7.8(16) . . . . ?
C9 C4 C3 C2 176.73(11) . . . . ?
C1 N1 C3 C2 1.40(9) . . . . ?
C1 N1 C3 C4 -179.56(11) . . . . ?
C1 C2 C3 N1 -1.35(8) . . . . ?
C1 C2 C3 C4 179.67(12) . . . . ?
C1 C2 C14 O6 105.79(11) . . . . ?
C1 C2 C14 O5 -73.38(14) . . . . ?
C8 C9 C4 C5 0.30(17) . . . . ?
C8 C9 C4 C3 -179.66(11) . . . . ?
C8 C7 C6 C5 0.20(19) . . . . ?
C2 C1 C10 O2 137.51(9) . . . . ?
C2 C1 C10 O1 -43.99(15) . . . . ?
C2 C1 C3 N1 178.23(11) . . . . ?
C2 C1 C3 C4 -175.7(16) . . . . ?
C2 C1 C12 O3 78.86(13) . . . . ?
C2 C1 C12 O4 -100.11(10) . . . . ?
C5 C4 C3 N1 178.04(11) . . . . ?
C5 C4 C3 C1 172.2(15) . . . . ?
C5 C4 C3 C2 -3.23(18) . . . . ?
C10 C1 C2 C3 -115.08(10) . . . . ?
C10 C1 C2 C14 -0.18(13) . . . . ?
C10 C1 C3 N1 -86.84(11) . . . . ?
C10 C1 C3 C2 94.92(11) . . . . ?
C10 C1 C3 C4 -80.7(16) . . . . ?
C10 C1 C12 O3 -50.56(14) . . . . ?
C10 C1 C12 O4 130.47(9) . . . . ?
C11 O2 C10 O1 4.41(17) . . . . ?
C11 O2 C10 C1 -177.12(9) . . . . ?
C6 C7 C8 C9 0.35(19) . . . . ?
C6 C5 C4 C9 0.26(17) . . . . ?
C6 C5 C4 C3 -179.78(10) . . . . ?
C13 O4 C12 O3 -6.25(17) . . . . ?
C13 O4 C12 C1 172.67(10) . . . . ?
C4 C9 C8 C7 -0.60(18) . . . . ?
C4 C5 C6 C7 -0.51(18) . . . . ?
C3 N1 C1 C2 -1.32(8) . . . . ?
C3 N1 C1 C10 116.45(10) . . . . ?
C3 N1 C1 C12 -115.87(10) . . . . ?
C3 C1 C2 C14 114.90(11) . . . . ?
C3 C1 C10 O2 81.76(12) . . . . ?
C3 C1 C10 O1 -99.75(13) . . . . ?
C3 C1 C12 O3 132.82(11) . . . . ?
C3 C1 C12 O4 -46.15(13) . . . . ?
C3 C2 C14 O6 -162.67(9) . . . . ?
C3 C2 C14 O5 18.15(16) . . . . ?
C12 C1 C2 C3 119.17(9) . . . . ?
C12 C1 C2 C14 -125.93(10) . . . . ?
C12 C1 C10 O2 -94.91(11) . . . . ?
C12 C1 C10 O1 83.58(13) . . . . ?
C12 C1 C3 N1 89.25(11) . . . . ?
C12 C1 C3 C2 -88.98(11) . . . . ?
C12 C1 C3 C4 95.4(16) . . . . ?
C15 O6 C14 O5 6.04(17) . . . . ?
C15 O6 C14 C2 -173.11(10) . . . . ?
C14 C2 C3 N1 -114.77(10) . . . . ?
C14 C2 C3 C1 -113.42(11) . . . . ?
C14 C2 C3 C4 66.25(15) . . . . ?

