# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1547228'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N2 O5 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H19 N2 O5 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.34
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_Int_Tables_number      43

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z
3 1/4-x,1/4+y,1/4+z
4 3/4+x,3/4-y,1/4+z
5 x,1/2+y,1/2+z
6 -x,1/2-y,1/2+z
7 1/4-x,3/4+y,3/4+z
8 3/4+x,1/4-y,3/4+z
9 1/2+x,y,1/2+z
10 1/2-x,-y,1/2+z
11 3/4-x,1/4+y,3/4+z
12 1/4+x,3/4-y,3/4+z
13 1/2+x,1/2+y,z
14 1/2-x,1/2-y,z
15 3/4-x,3/4+y,1/4+z
16 1/4+x,1/4-y,1/4+z

_cell_length_a                   27.560(4)
_cell_length_b                   30.440(4)
_cell_length_c                   9.2142(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7730.0(19)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2930
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.4

_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             3328
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku,1998)'
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.952

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            8930
_diffrn_reflns_av_R_equivalents  0.1370
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2841
_reflns_number_gt                2692
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.959
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  "PLATON (Spek, 2003)'"

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.1147
_refine_ls_wR_factor_ref         0.2633
_refine_ls_wR_factor_gt          0.2605
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.256

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P Uani 0.34791(4) 0.08953(4) 0.43923(15) 1.000 0.0318(5) . .
O1 O Uani 0.14253(13) 0.10368(13) 0.6425(5) 1.000 0.0428(14) . .
O2 O Uani 0.23408(15) 0.18636(13) 0.3141(5) 1.000 0.0440(12) . .
O3 O Uani 0.35514(16) 0.03896(14) 0.4402(7) 1.000 0.0563(16) . .
O4 O Uani 0.37449(14) 0.11488(13) 0.5493(6) 1.000 0.0453(14) . .
O5 O Uani 0.36075(16) 0.10162(15) 0.2784(5) 1.000 0.0473(16) . .
N1 N Uani 0.25527(16) 0.08267(14) 0.3616(5) 1.000 0.0327(12) . .
N2 N Uani 0.20898(15) 0.09521(13) 0.3939(5) 1.000 0.0320(14) . .
C1 C Uani 0.1761(2) 0.25222(17) 0.5031(8) 1.000 0.0440(19) . .
C2 C Uani 0.1435(2) 0.27188(19) 0.5982(9) 1.000 0.051(2) . .
C3 C Uani 0.1154(2) 0.2480(2) 0.6915(9) 1.000 0.055(2) . .
C4 C Uani 0.1200(2) 0.20211(18) 0.7005(8) 1.000 0.0453(19) . .
C5 C Uani 0.15257(17) 0.18203(16) 0.6083(7) 1.000 0.0320(14) . .
C6 C Uani 0.16442(18) 0.13441(16) 0.5909(6) 1.000 0.0327(14) . .
C7 C Uani 0.20947(17) 0.13176(14) 0.4945(6) 1.000 0.0283(14) . .
C8 C Uani 0.21080(16) 0.17730(15) 0.4226(6) 1.000 0.0303(14) . .
C9 C Uani 0.18061(17) 0.20663(15) 0.5112(7) 1.000 0.0340(14) . .
C10 C Uani 0.2549(2) 0.12571(19) 0.8520(6) 1.000 0.0373(17) . .
C11 C Uani 0.2482(3) 0.1033(3) 0.9826(8) 1.000 0.053(2) . .
C12 C Uani 0.2405(3) 0.0579(3) 0.9831(8) 1.000 0.058(2) . .
C13 C Uani 0.2402(3) 0.0348(2) 0.8566(9) 1.000 0.054(2) . .
C14 C Uani 0.2473(2) 0.05653(19) 0.7264(8) 1.000 0.0433(19) . .
C15 C Uani 0.25449(16) 0.10150(15) 0.7225(5) 1.000 0.0277(14) . .
C16 C Uani 0.2632(3) 0.1745(2) 0.8583(9) 1.000 0.058(2) . .
C17 C Uani 0.25900(16) 0.12471(15) 0.5771(5) 1.000 0.0260(14) . .
C18 C Uani 0.28424(16) 0.09765(14) 0.4585(6) 1.000 0.0274(14) . .
C19 C Uani 0.3920(3) 0.0155(2) 0.3656(11) 1.000 0.071(3) . .
C20 C Uani 0.3587(3) 0.1471(2) 0.2353(9) 1.000 0.057(2) . .
H1 H Uiso 0.19410 0.26870 0.43720 1.000 0.0530 calc R
H2 H Uiso 0.14080 0.30230 0.59840 1.000 0.0610 calc R
H2A H Uiso 0.18320 0.08310 0.35950 1.000 0.0390 calc R
H3 H Uiso 0.09290 0.26230 0.74980 1.000 0.0660 calc R
H4 H Uiso 0.10180 0.18590 0.76640 1.000 0.0540 calc R
H11 H Uiso 0.24880 0.11860 1.06990 1.000 0.0630 calc R
H12 H Uiso 0.23560 0.04330 1.07060 1.000 0.0690 calc R
H13 H Uiso 0.23520 0.00460 0.85760 1.000 0.0650 calc R
H14 H Uiso 0.24730 0.04070 0.64010 1.000 0.0520 calc R
H16A H Uiso 0.23590 0.18940 0.81620 1.000 0.0870 calc R
H16B H Uiso 0.29200 0.18170 0.80510 1.000 0.0870 calc R
H16C H Uiso 0.26690 0.18340 0.95760 1.000 0.0870 calc R
H17 H Uiso 0.27560 0.15290 0.58960 1.000 0.0310 calc R
H19A H Uiso 0.42140 0.03230 0.36580 1.000 0.1070 calc R
H19B H Uiso 0.38190 0.01030 0.26730 1.000 0.1070 calc R
H19C H Uiso 0.39750 -0.01210 0.41320 1.000 0.1070 calc R
H20A H Uiso 0.32540 0.15630 0.23000 1.000 0.0850 calc R
H20B H Uiso 0.37360 0.15050 0.14190 1.000 0.0850 calc R
H20C H Uiso 0.37560 0.16470 0.30530 1.000 0.0850 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.552(4) . . yes
P1 O4 1.470(5) . . yes
P1 O5 1.567(5) . . yes
P1 C18 1.781(5) . . yes
O1 C6 1.210(6) . . yes
O2 C8 1.220(7) . . yes
O3 C19 1.419(10) . . yes
O5 C20 1.441(8) . . yes
N1 N2 1.365(6) . . yes
N1 C18 1.282(7) . . yes
N2 C7 1.448(6) . . yes
N2 H2A 0.8600 . . no
C1 C2 1.390(9) . . no
C1 C9 1.395(7) . . no
C2 C3 1.367(10) . . no
C3 C4 1.405(8) . . no
C4 C5 1.379(8) . . no
C5 C9 1.399(8) . . no
C5 C6 1.495(7) . . no
C6 C7 1.529(7) . . no
C7 C8 1.537(7) . . no
C7 C17 1.578(7) . . no
C8 C9 1.468(7) . . no
C10 C11 1.396(10) . . no
C10 C15 1.403(7) . . no
C10 C16 1.504(8) . . no
C11 C12 1.398(13) . . no
C12 C13 1.361(11) . . no
C13 C14 1.384(11) . . no
C14 C15 1.384(7) . . no
C15 C17 1.520(7) . . no
C17 C18 1.535(7) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C16 H16A 0.9600 . . no
C16 H16B 0.9600 . . no
C16 H16C 0.9600 . . no
C17 H17 0.9800 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no
C20 H20A 0.9600 . . no
C20 H20B 0.9600 . . no
C20 H20C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 O4 116.9(3) . . . yes
O3 P1 O5 102.1(3) . . . yes
O3 P1 C18 105.3(2) . . . yes
O4 P1 O5 114.6(3) . . . yes
O4 P1 C18 110.5(2) . . . yes
O5 P1 C18 106.5(2) . . . yes
P1 O3 C19 126.0(5) . . . yes
P1 O5 C20 118.5(4) . . . yes
N2 N1 C18 109.3(4) . . . yes
N1 N2 C7 110.2(4) . . . yes
N1 N2 H2A 125.00 . . . no
C7 N2 H2A 125.00 . . . no
C2 C1 C9 116.9(6) . . . no
C1 C2 C3 122.3(5) . . . no
C2 C3 C4 121.0(6) . . . no
C3 C4 C5 117.6(6) . . . no
C6 C5 C9 109.3(5) . . . no
C4 C5 C6 129.7(5) . . . no
C4 C5 C9 121.1(5) . . . no
C5 C6 C7 106.9(4) . . . no
O1 C6 C7 126.3(4) . . . yes
O1 C6 C5 126.8(5) . . . yes
N2 C7 C8 114.7(4) . . . yes
N2 C7 C17 102.3(4) . . . yes
C6 C7 C17 115.4(4) . . . no
C8 C7 C17 108.1(4) . . . no
C6 C7 C8 102.8(4) . . . no
N2 C7 C6 113.9(4) . . . yes
C7 C8 C9 107.2(4) . . . no
O2 C8 C7 124.8(4) . . . yes
O2 C8 C9 128.1(5) . . . yes
C1 C9 C5 121.1(5) . . . no
C1 C9 C8 128.7(5) . . . no
C5 C9 C8 110.1(4) . . . no
C11 C10 C15 118.4(6) . . . no
C15 C10 C16 123.6(5) . . . no
C11 C10 C16 118.0(6) . . . no
C10 C11 C12 120.4(7) . . . no
C11 C12 C13 120.6(7) . . . no
C12 C13 C14 119.6(6) . . . no
C13 C14 C15 121.0(6) . . . no
C10 C15 C17 120.3(4) . . . no
C10 C15 C14 119.9(5) . . . no
C14 C15 C17 119.6(5) . . . no
C7 C17 C18 97.0(4) . . . no
C15 C17 C18 114.5(4) . . . no
C7 C17 C15 114.7(4) . . . no
N1 C18 C17 113.9(4) . . . yes
P1 C18 N1 119.7(4) . . . yes
P1 C18 C17 126.3(3) . . . yes
C2 C1 H1 122.00 . . . no
C9 C1 H1 122.00 . . . no
C1 C2 H2 119.00 . . . no
C3 C2 H2 119.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 119.00 . . . no
C10 C16 H16A 109.00 . . . no
C10 C16 H16B 109.00 . . . no
C10 C16 H16C 109.00 . . . no
H16A C16 H16B 110.00 . . . no
H16A C16 H16C 110.00 . . . no
H16B C16 H16C 110.00 . . . no
C7 C17 H17 110.00 . . . no
C15 C17 H17 110.00 . . . no
C18 C17 H17 110.00 . . . no
O3 C19 H19A 110.00 . . . no
O3 C19 H19B 109.00 . . . no
O3 C19 H19C 109.00 . . . no
H19A C19 H19B 110.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 109.00 . . . no
O5 C20 H20A 109.00 . . . no
O5 C20 H20B 110.00 . . . no
O5 C20 H20C 109.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 110.00 . . . no
H20B C20 H20C 110.00 . . . no

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
O4 P1 O3 C19 -88.1(7) . . . . no
O5 P1 O3 C19 37.9(7) . . . . no
C18 P1 O3 C19 148.9(6) . . . . no
O3 P1 O5 C20 -179.3(5) . . . . no
O4 P1 O5 C20 -51.9(5) . . . . no
C18 P1 O5 C20 70.6(5) . . . . no
O3 P1 C18 C17 123.6(4) . . . . no
O4 P1 C18 C17 -3.5(5) . . . . no
O5 P1 C18 C17 -128.5(4) . . . . no
O5 P1 C18 N1 46.3(5) . . . . no
O3 P1 C18 N1 -61.6(5) . . . . no
O4 P1 C18 N1 171.4(4) . . . . no
N2 N1 C18 P1 -176.0(3) . . . . no
N2 N1 C18 C17 -0.6(6) . . . . no
C18 N1 N2 C7 18.5(6) . . . . no
N1 N2 C7 C6 -152.5(4) . . . . no
N1 N2 C7 C8 89.4(5) . . . . no
N1 N2 C7 C17 -27.2(5) . . . . no
C2 C1 C9 C8 178.1(6) . . . . no
C2 C1 C9 C5 1.6(9) . . . . no
C9 C1 C2 C3 -2.8(10) . . . . no
C1 C2 C3 C4 3.2(11) . . . . no
C2 C3 C4 C5 -2.3(10) . . . . no
C3 C4 C5 C6 -178.6(6) . . . . no
C3 C4 C5 C9 1.1(9) . . . . no
C9 C5 C6 O1 -169.1(6) . . . . no
C4 C5 C9 C8 -178.0(5) . . . . no
C9 C5 C6 C7 10.7(6) . . . . no
C4 C5 C9 C1 -0.8(9) . . . . no
C4 C5 C6 O1 10.7(10) . . . . no
C4 C5 C6 C7 -169.6(6) . . . . no
C6 C5 C9 C1 178.9(5) . . . . no
C6 C5 C9 C8 1.8(6) . . . . no
O1 C6 C7 C8 161.9(5) . . . . no
C5 C6 C7 C8 -17.8(5) . . . . no
O1 C6 C7 C17 -80.7(7) . . . . no
C5 C6 C7 N2 -142.5(4) . . . . no
O1 C6 C7 N2 37.2(8) . . . . no
C5 C6 C7 C17 99.6(5) . . . . no
N2 C7 C8 O2 -38.6(7) . . . . no
C6 C7 C8 O2 -162.7(5) . . . . no
C6 C7 C8 C9 19.0(5) . . . . no
N2 C7 C8 C9 143.1(4) . . . . no
C8 C7 C17 C18 -97.8(4) . . . . no
C17 C7 C8 O2 74.7(6) . . . . no
C17 C7 C8 C9 -103.6(4) . . . . no
N2 C7 C17 C15 -97.6(4) . . . . no
N2 C7 C17 C18 23.5(4) . . . . no
C6 C7 C17 C15 26.6(5) . . . . no
C6 C7 C17 C18 147.7(4) . . . . no
C8 C7 C17 C15 141.1(4) . . . . no
O2 C8 C9 C5 168.3(5) . . . . no
C7 C8 C9 C1 169.7(6) . . . . no
C7 C8 C9 C5 -13.5(6) . . . . no
O2 C8 C9 C1 -8.6(10) . . . . no
C15 C10 C11 C12 -1.0(10) . . . . no
C11 C10 C15 C14 0.3(8) . . . . no
C11 C10 C15 C17 176.8(5) . . . . no
C16 C10 C11 C12 -179.8(7) . . . . no
C16 C10 C15 C14 179.0(6) . . . . no
C16 C10 C15 C17 -4.5(8) . . . . no
C10 C11 C12 C13 1.1(12) . . . . no
C11 C12 C13 C14 -0.4(12) . . . . no
C12 C13 C14 C15 -0.3(11) . . . . no
C13 C14 C15 C10 0.3(8) . . . . no
C13 C14 C15 C17 -176.2(6) . . . . no
C10 C15 C17 C18 149.2(4) . . . . no
C14 C15 C17 C7 76.6(5) . . . . no
C14 C15 C17 C18 -34.4(6) . . . . no
C10 C15 C17 C7 -99.9(5) . . . . no
C7 C17 C18 P1 159.9(4) . . . . no
C15 C17 C18 P1 -78.9(5) . . . . no
C15 C17 C18 N1 106.0(5) . . . . no
C7 C17 C18 N1 -15.2(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 2.944(6) . . no
O1 C14 3.316(7) . . no
O1 C15 3.173(6) . . no
O1 C20 3.293(9) . 8_455 no
O2 N1 3.240(6) . . no
O2 C18 3.313(6) . . no
O2 N2 2.953(6) . . no
O3 N1 3.142(6) . . no
O4 C7 2.955(7) . 16_555 no
O4 C5 3.278(8) . 16_555 no
O4 C6 2.904(8) . 16_555 no
O4 C9 3.308(7) . 16_555 no
O4 C8 2.932(6) . 16_555 no
O4 N2 2.767(6) . 16_555 no
O5 N1 3.061(6) . . no
O1 H2A 2.9100 . . no
O1 H20B 2.3600 . 8_455 no
O2 H19A 2.6900 . 8_454 no
O2 H1 2.6600 . 14_555 no
O2 H20A 2.7900 . . no
O4 H2 2.6000 . 14_555 no
O4 H20C 2.7100 . . no
O4 H2A 2.3300 . 16_555 no
O5 H19A 2.8100 . . no
O5 H19B 2.8400 . . no
O5 H4 2.6800 . 16_554 no
N1 O2 3.240(6) . . no
N1 O3 3.142(6) . . no
N1 O5 3.061(6) . . no
N2 O1 2.944(6) . . no
N2 O2 2.953(6) . . no
N2 C14 3.448(8) . . no
N2 O4 2.767(6) . 8_454 no
N1 H14 2.8700 . . no
N1 H13 2.6700 . 10_554 no
N1 H11 2.9100 . 1_554 no
C4 C12 3.595(10) . 8_454 no
C5 O4 3.278(8) . 8_454 no
C6 O4 2.904(8) . 8_454 no
C6 C10 3.475(8) . . no
C6 C14 3.521(8) . . no
C7 O4 2.955(7) . 8_454 no
C8 O4 2.932(6) . 8_454 no
C9 O4 3.308(7) . 8_454 no
C10 C6 3.475(8) . . no
C12 C4 3.595(10) . 16_555 no
C14 O1 3.316(7) . . no
C14 C6 3.521(8) . . no
C14 N2 3.448(8) . . no
C15 O1 3.173(6) . . no
C18 O2 3.313(6) . . no
C20 O1 3.293(9) . 16_554 no
C2 H16B 2.9600 . 14_555 no
C2 H2A 2.8200 . 3_555 no
C3 H19B 3.0500 . 8_455 no
C3 H2A 3.0100 . 3_555 no
C5 H16A 3.0000 . . no
C8 H1 3.1000 . 14_555 no
C12 H4 3.0900 . 16_555 no
C16 H17 2.5800 . . no
C17 H16B 2.8700 . . no
C17 H16A 3.0200 . . no
C18 H20A 2.9800 . . no
C18 H14 2.6200 . . no
C20 H19C 2.8500 . 11_554 no
H1 O2 2.6600 . 14_555 no
H1 C8 3.1000 . 14_555 no
H2 H2A 2.2500 . 3_555 no
H2 O4 2.6000 . 14_555 no
H2A O1 2.9100 . . no
H2A C2 2.8200 . 7_544 no
H2A C3 3.0100 . 7_544 no
H2A H2 2.2500 . 7_544 no
H2A O4 2.3300 . 8_454 no
H4 O5 2.6800 . 8_455 no
H4 C12 3.0900 . 8_454 no
H11 N1 2.9100 . 1_556 no
H11 H16C 2.2800 . . no
H13 N1 2.6700 . 10_555 no
H14 N1 2.8700 . . no
H14 C18 2.6200 . . no
H16A C5 3.0000 . . no
H16A C17 3.0200 . . no
H16B C17 2.8700 . . no
H16B H17 2.2200 . . no
H16B C2 2.9600 . 14_555 no
H16C H11 2.2800 . . no
H17 C16 2.5800 . . no
H17 H16B 2.2200 . . no
H19A O5 2.8100 . . no
H19A O2 2.6900 . 16_555 no
H19B O5 2.8400 . . no
H19B C3 3.0500 . 16_554 no
H19C C20 2.8500 . 15_545 no
H20A O2 2.7900 . . no
H20A C18 2.9800 . . no
H20B O1 2.3600 . 16_554 no
H20C O4 2.7100 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2A O4 0.8600 2.3300 2.767(6) 112.00 8_454 yes
C2 H2 O4 0.9300 2.6000 3.512(7) 169.00 14_555 yes
C20 H20B O1 0.9600 2.3600 3.293(9) 164.00 16_554 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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_xxx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1547535'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 O7 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C21 H21 N2 O7 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         444.37
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.4669(13)
_cell_length_b                   13.109(2)
_cell_length_c                   19.934(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.975(5)
_cell_angle_gamma                90
_cell_volume                     2104.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2862
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.340
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku,1998)'
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.942

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            13934
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.40
_reflns_number_total             3832
_reflns_number_gt                3132
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  "PLATON (Spek, 2003)'"


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0857P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.100

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P Uani 0.17509(6) 0.47186(4) 0.91026(2) 1.000 0.0339(2) . .
O1 O Uani 0.0486(3) 1.08188(15) 0.87183(10) 1.000 0.0863(7) . .
O2 O Uani 0.1892(2) 0.93466(12) 0.88610(7) 1.000 0.0575(5) . .
O3 O Uani 0.42661(19) 0.80086(14) 0.70139(8) 1.000 0.0628(6) . .
O4 O Uani 0.70556(17) 0.70732(13) 0.74003(7) 1.000 0.0535(5) . .
O5 O Uani 0.09818(17) 0.45653(12) 0.82919(7) 1.000 0.0487(5) . .
O6 O Uani 0.35558(16) 0.42920(11) 0.93093(7) 1.000 0.0436(4) . .
O7 O Uani 0.0662(2) 0.42781(12) 0.94665(8) 1.000 0.0595(6) . .
N1 N Uani 0.1431(2) 0.74477(13) 0.98146(8) 1.000 0.0422(5) . .
N2 N Uani 0.11979(19) 0.64489(12) 0.97192(8) 1.000 0.0378(5) . .
C1 C Uani 0.3947(3) 0.92370(18) 1.07844(11) 1.000 0.0540(7) . .
C2 C Uani 0.3791(3) 0.9953(2) 1.12658(12) 1.000 0.0634(9) . .
C3 C Uani 0.2806(3) 1.0804(2) 1.10502(14) 1.000 0.0641(9) . .
C4 C Uani 0.1970(3) 1.09704(18) 1.03493(13) 1.000 0.0574(8) . .
C5 C Uani 0.2146(3) 1.02481(15) 0.98739(11) 1.000 0.0446(6) . .
C6 C Uani 0.1398(3) 1.02201(17) 0.91085(12) 1.000 0.0553(8) . .
C7 C Uani 0.3035(3) 0.87707(15) 0.94392(10) 1.000 0.0434(6) . .
C8 C Uani 0.3099(2) 0.93937(15) 1.00798(10) 1.000 0.0413(6) . .
C9 C Uani 0.2440(2) 0.76971(15) 0.94408(9) 1.000 0.0364(6) . .
C10 C Uani 0.2864(2) 0.68421(14) 0.91052(9) 1.000 0.0328(5) . .
C11 C Uani 0.2035(2) 0.60393(14) 0.92995(9) 1.000 0.0323(5) . .
C12 C Uani 0.3976(2) 0.68441(13) 0.86585(9) 1.000 0.0325(5) . .
C13 C Uani 0.3547(2) 0.74251(15) 0.80397(9) 1.000 0.0369(6) . .
C14 C Uani 0.4573(2) 0.74667(16) 0.76228(9) 1.000 0.0379(6) . .
C15 C Uani 0.6089(2) 0.69423(15) 0.78266(9) 1.000 0.0363(6) . .
C16 C Uani 0.6514(2) 0.63655(16) 0.84348(9) 1.000 0.0407(6) . .
C17 C Uani 0.5450(2) 0.63072(15) 0.88446(9) 1.000 0.0391(6) . .
C18 C Uani 0.2656(3) 0.8416(3) 0.67208(14) 1.000 0.0897(13) . .
C19 C Uani 0.8719(3) 0.6725(3) 0.76513(15) 1.000 0.0833(12) . .
C20 C Uani 0.1854(3) 0.4677(2) 0.77803(10) 1.000 0.0587(8) . .
C21 C Uani 0.3804(3) 0.32054(18) 0.92430(12) 1.000 0.0643(9) . .
H1 H Uiso 0.46070 0.86620 1.09300 1.000 0.0650 calc R
H2 H Uiso 0.43580 0.98610 1.17420 1.000 0.0760 calc R
H2A H Uiso 0.05710 0.61050 0.99510 1.000 0.0450 . R
H3 H Uiso 0.27060 1.12730 1.13850 1.000 0.0770 calc R
H4 H Uiso 0.13130 1.15460 1.02020 1.000 0.0690 calc R
H7 H Uiso 0.41380 0.87640 0.93760 1.000 0.0520 calc R
H13 H Uiso 0.25550 0.77880 0.79080 1.000 0.0440 calc R
H16 H Uiso 0.75160 0.60140 0.85720 1.000 0.0490 calc R
H17 H Uiso 0.57350 0.59030 0.92480 1.000 0.0470 calc R
H18A H Uiso 0.25790 0.87480 0.62830 1.000 0.1340 calc R
H18B H Uiso 0.24380 0.89010 0.70420 1.000 0.1340 calc R
H18C H Uiso 0.18540 0.78750 0.66380 1.000 0.1340 calc R
H19A H Uiso 0.93030 0.69320 0.73310 1.000 0.1250 calc R
H19B H Uiso 0.87300 0.59940 0.76850 1.000 0.1250 calc R
H19C H Uiso 0.92520 0.70110 0.81080 1.000 0.1250 calc R
H20A H Uiso 0.11180 0.45200 0.73190 1.000 0.0880 calc R
H20B H Uiso 0.27840 0.42190 0.78930 1.000 0.0880 calc R
H20C H Uiso 0.22420 0.53660 0.77870 1.000 0.0880 calc R
H21A H Uiso 0.49690 0.30540 0.94120 1.000 0.0960 calc R
H21B H Uiso 0.33660 0.30090 0.87570 1.000 0.0960 calc R
H21C H Uiso 0.32400 0.28350 0.95170 1.000 0.0960 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O5 1.5577(14) . . yes
P1 O6 1.5586(15) . . yes
P1 O7 1.4569(18) . . yes
P1 C11 1.7751(19) . . yes
O1 C6 1.203(3) . . yes
O2 C6 1.363(3) . . yes
O2 C7 1.465(3) . . yes
O3 C14 1.360(2) . . yes
O3 C18 1.412(3) . . yes
O4 C15 1.360(2) . . yes
O4 C19 1.417(3) . . yes
O5 C20 1.439(3) . . yes
O6 C21 1.452(3) . . yes
N1 N2 1.329(2) . . yes
N1 C9 1.336(2) . . yes
N2 C11 1.363(2) . . yes
N2 H2A 0.9200 . . no
C1 C8 1.381(3) . . no
C1 C2 1.378(3) . . no
C2 C3 1.380(4) . . no
C3 C4 1.375(4) . . no
C4 C5 1.380(3) . . no
C5 C8 1.367(3) . . no
C5 C6 1.461(3) . . no
C7 C8 1.503(3) . . no
C7 C9 1.495(3) . . no
C9 C10 1.407(3) . . no
C10 C11 1.385(3) . . no
C10 C12 1.482(2) . . no
C12 C17 1.380(3) . . no
C12 C13 1.399(2) . . no
C13 C14 1.376(2) . . no
C14 C15 1.401(3) . . no
C15 C16 1.379(3) . . no
C16 C17 1.393(2) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C7 H7 0.9800 . . no
C13 H13 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17 0.9300 . . no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no
C20 H20A 0.9600 . . no
C20 H20B 0.9600 . . no
C20 H20C 0.9600 . . no
C21 H21A 0.9600 . . no
C21 H21B 0.9600 . . no
C21 H21C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 P1 O6 106.85(8) . . . yes
O5 P1 O7 109.83(9) . . . yes
O5 P1 C11 109.87(8) . . . yes
O6 P1 O7 116.47(9) . . . yes
O6 P1 C11 103.69(8) . . . yes
O7 P1 C11 109.87(9) . . . yes
C6 O2 C7 110.50(15) . . . yes
C14 O3 C18 117.45(18) . . . yes
C15 O4 C19 117.57(17) . . . yes
P1 O5 C20 125.47(14) . . . yes
P1 O6 C21 119.05(14) . . . yes
N2 N1 C9 104.69(16) . . . yes
N1 N2 C11 113.18(16) . . . yes
C11 N2 H2A 127.00 . . . no
N1 N2 H2A 120.00 . . . no
C2 C1 C8 118.4(2) . . . no
C1 C2 C3 120.8(2) . . . no
C2 C3 C4 121.1(2) . . . no
C3 C4 C5 117.3(2) . . . no
C4 C5 C8 122.3(2) . . . no
C4 C5 C6 129.1(2) . . . no
C6 C5 C8 108.57(18) . . . no
O2 C6 C5 108.46(18) . . . yes
O1 C6 O2 121.5(2) . . . yes
O1 C6 C5 130.1(2) . . . yes
O2 C7 C9 110.21(17) . . . yes
O2 C7 C8 103.32(16) . . . yes
C8 C7 C9 115.70(17) . . . no
C1 C8 C7 130.87(19) . . . no
C1 C8 C5 120.03(19) . . . no
C5 C8 C7 109.08(17) . . . no
N1 C9 C10 111.78(17) . . . yes
C7 C9 C10 127.81(17) . . . no
N1 C9 C7 120.36(17) . . . yes
C11 C10 C12 129.80(16) . . . no
C9 C10 C11 104.28(15) . . . no
C9 C10 C12 125.92(16) . . . no
N2 C11 C10 106.07(16) . . . yes
P1 C11 C10 136.48(14) . . . yes
P1 C11 N2 117.35(13) . . . yes
C10 C12 C17 121.80(16) . . . no
C10 C12 C13 119.37(16) . . . no
C13 C12 C17 118.81(16) . . . no
C12 C13 C14 120.90(17) . . . no
O3 C14 C13 125.25(17) . . . yes
C13 C14 C15 119.87(17) . . . no
O3 C14 C15 114.87(16) . . . yes
O4 C15 C16 125.05(17) . . . yes
O4 C15 C14 115.52(16) . . . yes
C14 C15 C16 119.41(16) . . . no
C15 C16 C17 120.35(17) . . . no
C12 C17 C16 120.62(17) . . . no
C2 C1 H1 121.00 . . . no
C8 C1 H1 121.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
O2 C7 H7 109.00 . . . no
C8 C7 H7 109.00 . . . no
C9 C7 H7 109.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C12 C17 H17 120.00 . . . no
C16 C17 H17 120.00 . . . no
O3 C18 H18A 110.00 . . . no
O3 C18 H18B 110.00 . . . no
O3 C18 H18C 109.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no
O4 C19 H19A 110.00 . . . no
O4 C19 H19B 109.00 . . . no
O4 C19 H19C 110.00 . . . no
H19A C19 H19B 109.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 109.00 . . . no
O5 C20 H20A 109.00 . . . no
O5 C20 H20B 109.00 . . . no
O5 C20 H20C 110.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 109.00 . . . no
H20B C20 H20C 109.00 . . . no
O6 C21 H21A 109.00 . . . no
O6 C21 H21B 109.00 . . . no
O6 C21 H21C 109.00 . . . no
H21A C21 H21B 110.00 . . . no
H21A C21 H21C 109.00 . . . no
H21B C21 H21C 109.00 . . . no

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
O6 P1 O5 C20 -37.3(2) . . . . no
O7 P1 O5 C20 -164.48(18) . . . . no
C11 P1 O5 C20 74.55(19) . . . . no
O5 P1 O6 C21 -66.33(16) . . . . no
O7 P1 O6 C21 56.81(16) . . . . no
C11 P1 O6 C21 177.61(14) . . . . no
O6 P1 C11 C10 56.9(2) . . . . no
O7 P1 C11 C10 -177.93(19) . . . . no
O6 P1 C11 N2 -127.37(14) . . . . no
O7 P1 C11 N2 -2.21(17) . . . . no
O5 P1 C11 N2 118.73(14) . . . . no
O5 P1 C11 C10 -57.0(2) . . . . no
C7 O2 C6 C5 -2.2(3) . . . . no
C6 O2 C7 C8 2.7(2) . . . . no
C6 O2 C7 C9 126.91(19) . . . . no
C7 O2 C6 O1 178.2(2) . . . . no
C18 O3 C14 C15 170.0(2) . . . . no
C18 O3 C14 C13 -11.6(3) . . . . no
C19 O4 C15 C14 168.1(2) . . . . no
C19 O4 C15 C16 -10.2(3) . . . . no
N2 N1 C9 C10 -0.4(2) . . . . no
N2 N1 C9 C7 -177.94(16) . . . . no
C9 N1 N2 C11 0.5(2) . . . . no
N1 N2 C11 C10 -0.5(2) . . . . no
N1 N2 C11 P1 -177.39(12) . . . . no
C2 C1 C8 C5 0.6(3) . . . . no
C2 C1 C8 C7 179.2(2) . . . . no
C8 C1 C2 C3 0.3(4) . . . . no
C1 C2 C3 C4 -0.9(4) . . . . no
C2 C3 C4 C5 0.6(4) . . . . no
C3 C4 C5 C6 179.2(3) . . . . no
C3 C4 C5 C8 0.3(4) . . . . no
C4 C5 C6 O2 -178.4(2) . . . . no
C6 C5 C8 C1 180.0(2) . . . . no
C4 C5 C6 O1 1.2(5) . . . . no
C4 C5 C8 C1 -0.9(4) . . . . no
C8 C5 C6 O2 0.6(3) . . . . no
C8 C5 C6 O1 -179.8(3) . . . . no
C4 C5 C8 C7 -179.8(2) . . . . no
C6 C5 C8 C7 1.2(3) . . . . no
O2 C7 C8 C5 -2.3(2) . . . . no
O2 C7 C9 N1 -90.7(2) . . . . no
C8 C7 C9 C10 -151.12(19) . . . . no
O2 C7 C8 C1 179.0(2) . . . . no
O2 C7 C9 C10 92.2(2) . . . . no
C9 C7 C8 C1 58.5(3) . . . . no
C9 C7 C8 C5 -122.9(2) . . . . no
C8 C7 C9 N1 26.1(3) . . . . no
N1 C9 C10 C11 0.1(2) . . . . no
C7 C9 C10 C11 177.45(18) . . . . no
C7 C9 C10 C12 -1.7(3) . . . . no
N1 C9 C10 C12 -179.11(16) . . . . no
C12 C10 C11 N2 179.36(17) . . . . no
C11 C10 C12 C13 119.6(2) . . . . no
C9 C10 C12 C13 -61.5(2) . . . . no
C9 C10 C12 C17 116.9(2) . . . . no
C12 C10 C11 P1 -4.6(3) . . . . no
C11 C10 C12 C17 -62.1(3) . . . . no
C9 C10 C11 N2 0.22(19) . . . . no
C9 C10 C11 P1 176.25(16) . . . . no
C17 C12 C13 C14 -0.2(3) . . . . no
C10 C12 C17 C16 -176.56(17) . . . . no
C13 C12 C17 C16 1.8(3) . . . . no
C10 C12 C13 C14 178.20(17) . . . . no
C12 C13 C14 C15 -1.6(3) . . . . no
C12 C13 C14 O3 -179.96(19) . . . . no
O3 C14 C15 O4 1.9(3) . . . . no
C13 C14 C15 C16 1.8(3) . . . . no
O3 C14 C15 C16 -179.66(18) . . . . no
C13 C14 C15 O4 -176.65(18) . . . . no
O4 C15 C16 C17 178.07(18) . . . . no
C14 C15 C16 C17 -0.2(3) . . . . no
C15 C16 C17 C12 -1.6(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C19 3.233(4) . 2_656 no
O1 C20 3.382(3) . 2_556 no
O2 N1 3.228(2) . . no
O3 O4 2.560(2) . . no
O3 C21 3.397(3) . 2_656 no
O4 O3 2.560(2) . . no
O6 C17 3.365(2) . . no
O7 N2 2.901(2) . . no
O7 C18 3.266(3) . 2_546 no
O7 N2 2.757(2) . 3_567 no
O1 H19A 2.6000 . 2_656 no
O1 H20A 2.7000 . 2_556 no
O2 H20A 2.8900 . 2_556 no
O3 H20B 2.9200 . 2_656 no
O3 H21B 2.8800 . 2_656 no
O4 H21B 2.5400 . 2_656 no
O4 H20B 2.8800 . 2_656 no
O5 H21B 2.8200 . . no
O5 H18B 2.9000 . 2_546 no
O5 H19B 2.6800 . 1_455 no
O6 H17 2.7600 . 3_667 no
O6 H20B 2.7000 . . no
O6 H17 2.8300 . . no
O7 H2A 2.5900 . . no
O7 H18A 2.7800 . 2_546 no
O7 H21C 2.8700 . . no
O7 H2A 1.8500 . 3_567 no
N1 O2 3.228(2) . . no
N1 C1 3.352(3) . . no
N2 O7 2.901(2) . . no
N2 O7 2.757(2) . 3_567 no
N1 H4 2.6600 . 3_577 no
C1 N1 3.352(3) . . no
C7 C13 3.439(3) . . no
C12 C20 3.525(3) . . no
C13 C7 3.439(3) . . no
C17 O6 3.365(2) . . no
C18 O7 3.266(3) . 2_556 no
C19 O1 3.233(4) . 2_646 no
C20 C12 3.525(3) . . no
C20 O1 3.382(3) . 2_546 no
C20 C21 3.461(3) . . no
C21 O3 3.397(3) . 2_646 no
C21 C20 3.461(3) . . no
C2 H7 2.9900 . 3_677 no
C3 H7 3.0200 . 3_677 no
C9 H13 3.0900 . . no
C9 H21A 2.8100 . 3_667 no
C10 H21A 2.9600 . 3_667 no
C10 H19C 3.1000 . 1_455 no
C11 H19C 3.0600 . 1_455 no
C12 H20C 2.7100 . . no
C12 H7 2.8800 . . no
C13 H7 3.1000 . . no
C13 H18B 2.7300 . . no
C13 H20C 2.9000 . . no
C13 H18C 2.7800 . . no
C14 H3 3.0200 . 3_677 no
C15 H3 2.8300 . 3_677 no
C16 H19C 2.7300 . . no
C16 H19B 2.7800 . . no
C18 H13 2.5300 . . no
C19 H16 2.5400 . . no
C20 H21B 2.9400 . . no
C21 H20B 2.8800 . . no
C21 H1 2.8600 . 3_667 no
H1 C21 2.8600 . 3_667 no
H1 H21A 2.4100 . 3_667 no
H2A O7 2.5900 . . no
H2A O7 1.8500 . 3_567 no
H3 C14 3.0200 . 3_677 no
H3 C15 2.8300 . 3_677 no
H4 N1 2.6600 . 3_577 no
H7 C12 2.8800 . . no
H7 C13 3.1000 . . no
H7 C2 2.9900 . 3_677 no
H7 C3 3.0200 . 3_677 no
H13 C9 3.0900 . . no
H13 C18 2.5300 . . no
H13 H18B 2.2400 . . no
H13 H18C 2.4200 . . no
H16 C19 2.5400 . . no
H16 H19B 2.3000 . . no
H16 H19C 2.3600 . . no
H17 O6 2.8300 . . no
H17 O6 2.7600 . 3_667 no
H18A O7 2.7800 . 2_556 no
H18B C13 2.7300 . . no
H18B H13 2.2400 . . no
H18B O5 2.9000 . 2_556 no
H18C C13 2.7800 . . no
H18C H13 2.4200 . . no
H19A O1 2.6000 . 2_646 no
H19B O5 2.6800 . 1_655 no
H19B C16 2.7800 . . no
H19B H16 2.3000 . . no
H19C C10 3.1000 . 1_655 no
H19C C11 3.0600 . 1_655 no
H19C C16 2.7300 . . no
H19C H16 2.3600 . . no
H20A O1 2.7000 . 2_546 no
H20A O2 2.8900 . 2_546 no
H20B O6 2.7000 . . no
H20B C21 2.8800 . . no
H20B H21B 2.2800 . . no
H20B O3 2.9200 . 2_646 no
H20B O4 2.8800 . 2_646 no
H20C C12 2.7100 . . no
H20C C13 2.9000 . . no
H21A C9 2.8100 . 3_667 no
H21A C10 2.9600 . 3_667 no
H21A H1 2.4100 . 3_667 no
H21B O5 2.8200 . . no
H21B C20 2.9400 . . no
H21B H20B 2.2800 . . no
H21B O3 2.8800 . 2_646 no
H21B O4 2.5400 . 2_646 no
H21C O7 2.8700 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2A O7 0.9200 2.5900 2.901(2) 100.00 . yes
N2 H2A O7 0.9200 1.8500 2.757(2) 166.00 3_567 yes
C21 H21B O4 0.9600 2.5400 3.463(3) 162.00 2_646 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
