# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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 1023441'
_audit_update_record             
;
2014-09-09 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N2 O6 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            'C16 H21 N2 O6 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         368.32
_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                   10.018(2)
_cell_length_b                   13.304(3)
_cell_length_c                   13.868(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.637(3)
_cell_angle_gamma                90
_cell_volume                     1779.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    2729
_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          0.620
_exptl_crystal_size_mid          0.540
_exptl_crystal_size_min          0.510

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.910

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

# 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 Fiber
_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            13426
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.42
_reflns_number_total             3243
_reflns_number_gt                2874
_reflns_threshold_expression     >2sigma(I)

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.991
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'

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

# 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)+(0.0447P)²+0.5709P] 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         3243
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.047

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

# 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 1.03037(4) 0.79357(3) 0.99493(3) 1.000 0.0136(1) . .
O1 O Uani 0.40177(10) 0.64786(8) 0.74439(7) 1.000 0.0183(3) . .
O2 O Uani 0.55370(10) 0.55329(8) 0.64050(7) 1.000 0.0160(3) . .
O3 O Uani 0.82631(10) 0.52312(8) 0.71868(7) 1.000 0.0185(3) . .
O4 O Uani 0.94526(10) 0.83070(8) 0.89811(7) 1.000 0.0182(3) . .
O5 O Uani 1.13849(10) 0.71396(8) 0.97638(7) 1.000 0.0195(3) . .
O6 O Uani 1.11450(10) 0.87526(8) 1.06758(7) 1.000 0.0177(3) . .
N1 N Uani 0.86547(12) 0.70697(9) 1.19921(9) 1.000 0.0131(3) . .
N2 N Uani 0.96589(12) 0.75283(9) 1.16847(8) 1.000 0.0143(3) . .
C1 C Uani 0.61163(17) 0.61168(12) 1.22524(12) 1.000 0.0235(5) . .
C2 C Uani 0.65207(15) 0.60624(11) 1.14190(11) 1.000 0.0172(4) . .
C3 C Uani 0.76970(14) 0.66090(10) 1.12435(10) 1.000 0.0129(4) . .
C4 C Uani 0.80944(14) 0.67815(10) 1.03713(10) 1.000 0.0125(4) . .
C5 C Uani 0.93203(14) 0.73651(11) 1.06922(10) 1.000 0.0127(4) . .
C6 C Uani 0.74090(14) 0.64420(10) 0.93399(10) 1.000 0.0131(4) . .
C7 C Uani 0.59932(14) 0.66023(11) 0.89223(10) 1.000 0.0143(4) . .
C8 C Uani 0.53798(14) 0.63218(11) 0.79335(10) 1.000 0.0147(4) . .
C9 C Uani 0.61713(14) 0.58589(11) 0.73679(10) 1.000 0.0137(4) . .
C10 C Uani 0.75818(14) 0.56930(11) 0.77919(10) 1.000 0.0141(4) . .
C11 C Uani 0.82027(14) 0.59857(10) 0.87770(10) 1.000 0.0137(4) . .
C12 C Uani 0.31497(15) 0.68848(14) 0.80165(12) 1.000 0.0249(5) . .
C13 C Uani 0.57628(16) 0.61967(12) 0.56455(10) 1.000 0.0198(4) . .
C14 C Uani 0.97330(15) 0.51124(12) 0.75779(11) 1.000 0.0199(5) . .
C15 C Uani 1.23945(16) 0.67036(13) 1.06146(12) 1.000 0.0263(5) . .
C16 C Uani 1.20089(15) 0.94653(12) 1.03155(11) 1.000 0.0209(5) . .
H1 H Uiso 0.8757(18) 0.7024(13) 1.2620(14) 1.000 0.024(5) . .
H1A H Uiso 0.65940 0.65250 1.27770 1.000 0.0280 calc R
H1B H Uiso 0.53560 0.57470 1.23130 1.000 0.0280 calc R
H2 H Uiso 0.91450 0.58770 0.90580 1.000 0.0160 calc R
H2A H Uiso 0.60200 0.56470 1.09100 1.000 0.0210 calc R
H7 H Uiso 0.54620 0.68950 0.93020 1.000 0.0170 calc R
H12A H Uiso 0.31750 0.64520 0.85750 1.000 0.0370 calc R
H12B H Uiso 0.22150 0.69330 0.76020 1.000 0.0370 calc R
H12C H Uiso 0.34770 0.75410 0.82560 1.000 0.0370 calc R
H13A H Uiso 0.53740 0.68440 0.57120 1.000 0.0300 calc R
H13B H Uiso 0.53250 0.59250 0.49960 1.000 0.0300 calc R
H13C H Uiso 0.67400 0.62640 0.57220 1.000 0.0300 calc R
H14A H Uiso 1.01540 0.57590 0.77520 1.000 0.0300 calc R
H14B H Uiso 1.01050 0.48050 0.70800 1.000 0.0300 calc R
H14C H Uiso 0.99230 0.46940 0.81630 1.000 0.0300 calc R
H15A H Uiso 1.30710 0.72020 1.09170 1.000 0.0390 calc R
H15B H Uiso 1.28470 0.61480 1.03930 1.000 0.0390 calc R
H15C H Uiso 1.19330 0.64720 1.10970 1.000 0.0390 calc R
H16A H Uiso 1.21780 0.92140 0.97110 1.000 0.0310 calc R
H16B H Uiso 1.28750 0.95500 1.08150 1.000 0.0310 calc R
H16C H Uiso 1.15410 1.01010 1.01840 1.000 0.0310 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 O4 1.4686(11) . . yes
P1 O5 1.5847(12) . . yes
P1 O6 1.5649(11) . . yes
P1 C5 1.7764(15) . . yes
O1 C8 1.3664(18) . . yes
O1 C12 1.4321(19) . . yes
O2 C9 1.3848(17) . . yes
O2 C13 1.4384(18) . . yes
O3 C10 1.3624(18) . . yes
O3 C14 1.4342(19) . . yes
O5 C15 1.4520(19) . . yes
O6 C16 1.4597(19) . . yes
N1 N2 1.3406(18) . . yes
N1 C3 1.3554(19) . . yes
N2 C5 1.3435(17) . . yes
N1 H1 0.851(19) . . no
C1 C2 1.326(2) . . no
C2 C3 1.460(2) . . no
C3 C4 1.391(2) . . no
C4 C5 1.419(2) . . no
C4 C6 1.4805(19) . . no
C6 C11 1.395(2) . . no
C6 C7 1.396(2) . . no
C7 C8 1.3939(19) . . no
C8 C9 1.400(2) . . no
C9 C10 1.394(2) . . no
C10 C11 1.3953(19) . . no
C1 H1A 0.9300 . . no
C1 H1B 0.9300 . . no
C2 H2A 0.9300 . . no
C7 H7 0.9300 . . no
C11 H2 0.9300 . . no
C12 H12A 0.9600 . . no
C12 H12B 0.9600 . . no
C12 H12C 0.9600 . . no
C13 H13A 0.9600 . . no
C13 H13B 0.9600 . . no
C13 H13C 0.9600 . . no
C14 H14A 0.9600 . . no
C14 H14B 0.9600 . . no
C14 H14C 0.9600 . . no
C15 H15A 0.9600 . . no
C15 H15B 0.9600 . . no
C15 H15C 0.9600 . . no
C16 H16A 0.9600 . . no
C16 H16B 0.9600 . . no
C16 H16C 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
O4 P1 O5 109.28(6) . . . yes
O4 P1 O6 115.74(6) . . . yes
O4 P1 C5 113.45(7) . . . yes
O5 P1 O6 107.19(6) . . . yes
O5 P1 C5 108.59(6) . . . yes
O6 P1 C5 102.13(6) . . . yes
C8 O1 C12 117.15(11) . . . yes
C9 O2 C13 113.08(11) . . . yes
C10 O3 C14 116.78(11) . . . yes
P1 O5 C15 119.47(9) . . . yes
P1 O6 C16 119.79(9) . . . yes
N2 N1 C3 113.53(11) . . . yes
N1 N2 C5 104.38(11) . . . yes
C3 N1 H1 128.1(12) . . . no
N2 N1 H1 117.7(13) . . . no
C1 C2 C3 124.63(14) . . . no
N1 C3 C2 122.28(12) . . . yes
C2 C3 C4 131.33(13) . . . no
N1 C3 C4 106.39(12) . . . yes
C3 C4 C6 128.54(13) . . . no
C3 C4 C5 104.12(12) . . . no
C5 C4 C6 127.34(12) . . . no
P1 C5 C4 128.33(10) . . . yes
P1 C5 N2 119.92(11) . . . yes
N2 C5 C4 111.58(12) . . . yes
C7 C6 C11 120.20(12) . . . no
C4 C6 C11 119.19(13) . . . no
C4 C6 C7 120.59(12) . . . no
C6 C7 C8 119.76(13) . . . no
C7 C8 C9 120.20(13) . . . no
O1 C8 C7 124.36(13) . . . yes
O1 C8 C9 115.43(12) . . . yes
C8 C9 C10 119.76(12) . . . no
O2 C9 C8 119.75(12) . . . yes
O2 C9 C10 120.44(12) . . . yes
O3 C10 C9 115.51(12) . . . yes
O3 C10 C11 124.32(13) . . . yes
C9 C10 C11 120.17(13) . . . no
C6 C11 C10 119.91(13) . . . no
C2 C1 H1A 120.00 . . . no
C2 C1 H1B 120.00 . . . no
H1A C1 H1B 120.00 . . . no
C1 C2 H2A 118.00 . . . no
C3 C2 H2A 118.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C6 C11 H2 120.00 . . . no
C10 C11 H2 120.00 . . . no
O1 C12 H12A 109.00 . . . no
O1 C12 H12B 109.00 . . . no
O1 C12 H12C 109.00 . . . no
H12A C12 H12B 109.00 . . . no
H12A C12 H12C 110.00 . . . no
H12B C12 H12C 109.00 . . . no
O2 C13 H13A 109.00 . . . no
O2 C13 H13B 109.00 . . . no
O2 C13 H13C 109.00 . . . no
H13A C13 H13B 109.00 . . . no
H13A C13 H13C 110.00 . . . no
H13B C13 H13C 109.00 . . . no
O3 C14 H14A 109.00 . . . no
O3 C14 H14B 109.00 . . . no
O3 C14 H14C 109.00 . . . no
H14A C14 H14B 109.00 . . . no
H14A C14 H14C 109.00 . . . no
H14B C14 H14C 110.00 . . . no
O5 C15 H15A 110.00 . . . no
O5 C15 H15B 109.00 . . . no
O5 C15 H15C 109.00 . . . no
H15A C15 H15B 109.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
O6 C16 H16A 109.00 . . . no
O6 C16 H16B 109.00 . . . no
O6 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 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
O4 P1 O5 C15 176.78(11) . . . . no
O6 P1 O5 C15 50.64(12) . . . . no
C5 P1 O5 C15 -59.00(12) . . . . no
O4 P1 O6 C16 -50.66(12) . . . . no
O5 P1 O6 C16 71.54(11) . . . . no
C5 P1 O6 C16 -174.40(11) . . . . no
O6 P1 C5 C4 160.26(13) . . . . no
O6 P1 C5 N2 -14.60(13) . . . . no
O4 P1 C5 N2 -139.86(11) . . . . no
O5 P1 C5 N2 98.43(12) . . . . no
O4 P1 C5 C4 35.00(16) . . . . no
O5 P1 C5 C4 -86.71(14) . . . . no
C12 O1 C8 C9 175.67(13) . . . . no
C12 O1 C8 C7 -5.2(2) . . . . no
C13 O2 C9 C10 -80.27(17) . . . . no
C13 O2 C9 C8 102.32(15) . . . . no
C14 O3 C10 C9 175.86(13) . . . . no
C14 O3 C10 C11 -4.8(2) . . . . no
C3 N1 N2 C5 0.79(16) . . . . no
N2 N1 C3 C4 -0.38(16) . . . . no
N2 N1 C3 C2 179.73(13) . . . . no
N1 N2 C5 P1 174.77(10) . . . . no
N1 N2 C5 C4 -0.89(16) . . . . no
C1 C2 C3 N1 13.5(2) . . . . no
C1 C2 C3 C4 -166.34(16) . . . . no
C2 C3 C4 C5 179.70(15) . . . . no
N1 C3 C4 C5 -0.18(15) . . . . no
N1 C3 C4 C6 179.89(13) . . . . no
C2 C3 C4 C6 -0.2(3) . . . . no
C5 C4 C6 C7 -129.38(16) . . . . no
C3 C4 C6 C11 -131.37(16) . . . . no
C6 C4 C5 P1 5.4(2) . . . . no
C3 C4 C6 C7 50.5(2) . . . . no
C3 C4 C5 N2 0.69(16) . . . . no
C6 C4 C5 N2 -179.39(13) . . . . no
C5 C4 C6 C11 48.7(2) . . . . no
C3 C4 C5 P1 -174.52(11) . . . . no
C4 C6 C11 C10 -177.78(13) . . . . no
C11 C6 C7 C8 -1.2(2) . . . . no
C7 C6 C11 C10 0.3(2) . . . . no
C4 C6 C7 C8 176.86(13) . . . . no
C6 C7 C8 C9 1.6(2) . . . . no
C6 C7 C8 O1 -177.51(13) . . . . no
O1 C8 C9 O2 -4.4(2) . . . . no
O1 C8 C9 C10 178.15(13) . . . . no
C7 C8 C9 C10 -1.0(2) . . . . no
C7 C8 C9 O2 176.44(13) . . . . no
O2 C9 C10 O3 2.1(2) . . . . no
C8 C9 C10 C11 0.1(2) . . . . no
O2 C9 C10 C11 -177.32(13) . . . . no
C8 C9 C10 O3 179.51(13) . . . . no
O3 C10 C11 C6 -179.12(13) . . . . no
C9 C10 C11 C6 0.2(2) . . . . 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
P1 C11 3.4582(16) . . no
P1 H2 3.1000 . . no
P1 H16C 3.1800 . 3_777 no
P1 H1 3.184(19) . 4_564 no
O1 O2 2.6753(16) . . no
O1 C16 3.3372(19) . 4_464 no
O2 O3 2.6831(16) . . no
O2 O1 2.6753(16) . . no
O3 C13 3.0994(19) . . no
O3 O2 2.6831(16) . . no
O4 C6 3.3383(19) . . no
O4 C11 3.3158(19) . . no
O4 N1 2.7037(16) . 4_564 no
O5 C12 3.380(2) . 1_655 no
O6 N2 2.8196(17) . . no
O1 H15A 2.7200 . 4_464 no
O1 H16B 2.6300 . 4_464 no
O2 H16B 2.5700 . 4_464 no
O2 H13B 2.7200 . 3_666 no
O2 H1B 2.7800 . 3_667 no
O3 H13C 2.5800 . . no
O3 H16A 2.8900 . 2_746 no
O4 H16C 2.7300 . 3_777 no
O4 H14B 2.5900 . 2_756 no
O4 H1A 2.9100 . 4_564 no
O4 H16A 2.9100 . . no
O4 H1 1.880(19) . 4_564 no
O5 H12A 2.8900 . 1_655 no
O5 H16A 2.8800 . . no
O5 H2 2.7600 . . no
O6 H15A 2.7800 . . no
O6 H12B 2.7500 . 4_665 no
N1 C14 3.297(2) . 3_767 no
N1 C10 3.448(2) . 4_565 no
N1 O4 2.7037(16) . 4_565 no
N2 C14 3.368(2) . 4_565 no
N2 O6 2.8196(17) . . no
N1 H14B 2.9300 . 3_767 no
N1 H14C 2.7800 . 3_767 no
N1 H1A 2.6800 . . no
N2 H12B 2.6300 . 4_665 no
N2 H14A 2.6900 . 4_565 no
C1 C8 3.554(2) . 3_667 no
C2 C7 3.435(2) . . no
C3 C14 3.504(2) . 3_767 no
C3 C13 3.478(2) . 4_565 no
C6 O4 3.3383(19) . . no
C7 C2 3.435(2) . . no
C8 C1 3.554(2) . 3_667 no
C10 N1 3.448(2) . 4_564 no
C11 P1 3.4582(16) . . no
C11 O4 3.3158(19) . . no
C12 O5 3.380(2) . 1_455 no
C13 C3 3.478(2) . 4_564 no
C13 O3 3.0994(19) . . no
C14 N1 3.297(2) . 3_767 no
C14 C3 3.504(2) . 3_767 no
C14 N2 3.368(2) . 4_564 no
C16 O1 3.3372(19) . 4_665 no
C1 H1 2.826(19) . . no
C2 H13A 3.0700 . 4_565 no
C2 H7 3.0500 . . no
C3 H14C 2.8800 . 3_767 no
C3 H13C 3.0100 . 4_565 no
C3 H7 3.0300 . . no
C3 H13A 3.0400 . 4_565 no
C4 H13C 3.0300 . 4_565 no
C5 H15C 2.7900 . . no
C5 H2 2.9800 . . no
C6 H2A 3.0700 . . no
C7 H12A 2.7400 . . no
C7 H12C 2.7400 . . no
C7 H1A 3.1000 . 4_564 no
C7 H2A 3.0300 . . no
C8 H1B 2.8500 . 3_667 no
C9 H1B 2.7300 . 3_667 no
C10 H13C 2.8700 . . no
C11 H14C 2.7300 . . no
C11 H14A 2.7300 . . no
C12 H7 2.5100 . . no
C13 H13B 3.0700 . 3_666 no
C14 H2 2.5000 . . no
H1 C1 2.826(19) . . no
H1 H1A 2.3300 . . no
H1 P1 3.184(19) . 4_565 no
H1 O4 1.880(19) . 4_565 no
H1A N1 2.6800 . . no
H1A H1 2.3300 . . no
H1A O4 2.9100 . 4_565 no
H1A C7 3.1000 . 4_565 no
H1B O2 2.7800 . 3_667 no
H1B C8 2.8500 . 3_667 no
H1B C9 2.7300 . 3_667 no
H2 P1 3.1000 . . no
H2 O5 2.7600 . . no
H2 C5 2.9800 . . no
H2 C14 2.5000 . . no
H2 H14A 2.3100 . . no
H2 H14C 2.2700 . . no
H2A C6 3.0700 . . no
H2A C7 3.0300 . . no
H7 C2 3.0500 . . no
H7 C3 3.0300 . . no
H7 C12 2.5100 . . no
H7 H12A 2.3200 . . no
H7 H12C 2.2900 . . no
H7 H13A 2.6000 . 4_565 no
H12A O5 2.8900 . 1_455 no
H12A C7 2.7400 . . no
H12A H7 2.3200 . . no
H12B O6 2.7500 . 4_464 no
H12B N2 2.6300 . 4_464 no
H12C C7 2.7400 . . no
H12C H7 2.2900 . . no
H13A C2 3.0700 . 4_564 no
H13A C3 3.0400 . 4_564 no
H13A H7 2.6000 . 4_564 no
H13B O2 2.7200 . 3_666 no
H13B C13 3.0700 . 3_666 no
H13B H13B 2.5500 . 3_666 no
H13C O3 2.5800 . . no
H13C C10 2.8700 . . no
H13C C3 3.0100 . 4_564 no
H13C C4 3.0300 . 4_564 no
H14A C11 2.7300 . . no
H14A H2 2.3100 . . no
H14A N2 2.6900 . 4_564 no
H14B O4 2.5900 . 2_746 no
H14B N1 2.9300 . 3_767 no
H14C C11 2.7300 . . no
H14C H2 2.2700 . . no
H14C N1 2.7800 . 3_767 no
H14C C3 2.8800 . 3_767 no
H15A O6 2.7800 . . no
H15A O1 2.7200 . 4_665 no
H15C C5 2.7900 . . no
H16A O4 2.9100 . . no
H16A O5 2.8800 . . no
H16A O3 2.8900 . 2_756 no
H16B O1 2.6300 . 4_665 no
H16B O2 2.5700 . 4_665 no
H16C P1 3.1800 . 3_777 no
H16C O4 2.7300 . 3_777 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)
#
N1 H1 O4 0.851(19) 1.880(19) 2.7037(16) 162.6(18) 4_565 yes
C13 H13C O3 0.9600 2.5800 3.0994(19) 114.00 . yes
C14 H14B O4 0.9600 2.5900 3.473(2) 154.00 2_746 yes
C16 H16B O2 0.9600 2.5700 3.449(2) 152.00 4_665 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
