# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          ?
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   4.47500(10)
_cell_length_b                   13.8149(2)
_cell_length_c                   8.7194(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.575(2)
_cell_angle_gamma                90
_cell_volume                     537.330(19)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n '
_symmetry_space_group_name_Hall  'P -2yac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C5 P0.33 
# Dc =      1.30 Fooo =    260.00 Mu =      2.17 M =    211.14
# Found Formula = C2.67 H4.33 N0.67 O1.67 P0.33 
# Dc =      1.53 FOOO =    260.00 Mu =      2.65 M =    248.18

_chemical_formula_sum            'C8 H13 N2 O5 P'
_chemical_formula_moiety         'C8 H13 N2 O5 P'
_chemical_compound_source        ?
_chemical_formula_weight         248.17


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.230

_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.265

# Sheldrick geometric approximatio 0.95 0.96 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      175
_diffrn_reflns_number            10395
_reflns_number_total             2568
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 2568 
# Number of reflections with Friedels Law is 1337 
# Theoretical number of reflections is about 1423 


_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         28.959
_diffrn_measured_fraction_theta_max 0.940

_diffrn_reflns_theta_full        25.194
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -6
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              -11
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   1.67
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.21


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     2
_refine_ls_number_parameters     146
_oxford_refine_ls_R_factor_ref   0.0262
_refine_ls_wR_factor_ref         0.0379
_refine_ls_goodness_of_fit_ref   1.0405
_refine_ls_shift/su_max          0.0002867
_refine_ls_shift/su_mean         0.0000221


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2565
_refine_ls_R_factor_all          0.0262
_refine_ls_wR_factor_all         0.0379

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2382
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_gt          0.0361

_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_abs_structure_details 'Flack (1983), 1231 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 138. 178. 65.0 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.42145(13) 0.60022(3) 0.47188(9) 0.0152 1.0000 Uani . . . . . .
O2 O 0.2062(2) 0.60854(9) 0.59690(14) 0.0213 1.0000 Uani . . . . . .
O3 O 0.6810(3) 0.67522(9) 0.50806(18) 0.0303 1.0000 Uani . . . . . .
H31 H 0.8598 0.6566 0.5333 0.0460 1.0000 Uiso R . . . . .
O4 O 0.2730(3) 0.61569(9) 0.31275(15) 0.0287 1.0000 Uani . . . . . .
C5 C 0.6047(3) 0.48405(11) 0.4773(2) 0.0177 1.0000 Uani . . . . . .
C6 C 0.3897(4) 0.39788(12) 0.4525(2) 0.0194 1.0000 Uani . . . . . .
C7 C 0.5644(4) 0.30645(11) 0.4515(2) 0.0169 1.0000 Uani . . . . . .
N8 N 0.6122(3) 0.24407(10) 0.56672(17) 0.0171 1.0000 Uani . . . . . .
O9 O 0.4716(3) 0.25020(9) 0.70005(15) 0.0225 1.0000 Uani . . . . . .
H91 H 0.5645 0.2956 0.7487 0.0355 1.0000 Uiso R . . . . .
C10 C 0.8024(4) 0.17019(11) 0.5276(2) 0.0184 1.0000 Uani . . . . . .
C11 C 0.8686(4) 0.18959(11) 0.3798(2) 0.0175 1.0000 Uani . . . . . .
N12 N 0.7217(3) 0.27381(9) 0.33735(16) 0.0161 1.0000 Uani . . . . . .
H121 H 0.7248 0.3030 0.2526 0.0201 1.0000 Uiso R . . . . .
C13 C 1.0541(4) 0.13754(12) 0.2722(2) 0.0233 1.0000 Uani . . . . . .
H133 H 1.2196 0.1073 0.3288 0.0367 1.0000 Uiso R . . . . .
H132 H 1.1243 0.1828 0.2025 0.0348 1.0000 Uiso R . . . . .
H131 H 0.9282 0.0918 0.2187 0.0333 1.0000 Uiso R . . . . .
C14 C 0.9334(4) 0.09367(13) 0.6316(2) 0.0244 1.0000 Uani . . . . . .
O15 O 1.0573(4) 0.02628(10) 0.57475(17) 0.0454 1.0000 Uani . . . . . .
C16 C 0.9220(4) 0.10382(14) 0.80256(19) 0.0296 1.0000 Uani . . . . . .
H163 H 1.0593 0.0564 0.8525 0.0438 1.0000 Uiso R . . . . .
H162 H 0.7151 0.0932 0.8321 0.0433 1.0000 Uiso R . . . . .
H161 H 0.9831 0.1692 0.8346 0.0427 1.0000 Uiso R . . . . .
H62 H 0.2575 0.3931 0.5355 0.0230 1.0000 Uiso R . . . . .
H61 H 0.2761 0.4030 0.3513 0.0232 1.0000 Uiso R . . . . .
H51 H 0.7269 0.4740 0.5758 0.0199 1.0000 Uiso R . . . . .
H52 H 0.7522 0.4862 0.3957 0.0204 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.01428(18) 0.01346(17) 0.01771(19) -0.00035(19) 0.00073(15) 0.00192(19)
O2 0.0210(6) 0.0224(6) 0.0209(6) -0.0052(5) 0.0047(5) -0.0022(5)
O3 0.0167(6) 0.0167(6) 0.0575(9) -0.0022(6) 0.0040(6) -0.0012(5)
O4 0.0400(8) 0.0260(7) 0.0193(6) 0.0002(5) -0.0019(5) 0.0114(6)
C5 0.0145(7) 0.0129(7) 0.0256(9) -0.0007(6) 0.0004(6) 0.0020(6)
C6 0.0167(9) 0.0161(7) 0.0252(9) -0.0016(8) 0.0004(7) 0.0003(7)
C7 0.0153(8) 0.0150(7) 0.0202(8) -0.0023(6) -0.0003(6) -0.0045(6)
N8 0.0188(7) 0.0142(6) 0.0185(7) -0.0019(6) 0.0020(5) -0.0024(5)
O9 0.0266(6) 0.0238(6) 0.0181(6) -0.0043(5) 0.0080(5) -0.0057(5)
C10 0.0209(7) 0.0127(7) 0.0213(8) -0.0012(7) 0.0003(6) -0.0002(7)
C11 0.0165(8) 0.0126(7) 0.0230(8) -0.0005(7) -0.0012(6) -0.0022(6)
N12 0.0177(7) 0.0150(6) 0.0153(7) 0.0015(5) -0.0005(5) -0.0002(5)
C13 0.0264(9) 0.0187(8) 0.0253(9) -0.0014(7) 0.0049(7) 0.0028(7)
C14 0.0302(9) 0.0183(8) 0.0240(9) 0.0039(7) -0.0012(7) 0.0008(7)
O15 0.0717(11) 0.0314(8) 0.0332(8) 0.0057(7) 0.0049(7) 0.0264(8)
C16 0.0410(11) 0.0243(9) 0.0228(9) 0.0064(8) -0.0018(8) -0.0021(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.84(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . O2 . 1.5154(11) yes
P1 . O3 . 1.5695(12) yes
P1 . O4 . 1.5051(12) yes
P1 . C5 . 1.8011(15) yes
O3 . H31 . 0.853 no
C5 . C6 . 1.535(2) yes
C5 . H51 . 0.990 no
C5 . H52 . 1.008 no
C6 . C7 . 1.486(2) yes
C6 . H62 . 0.973 no
C6 . H61 . 0.985 no
C7 . N8 . 1.328(2) yes
C7 . N12 . 1.342(2) yes
N8 . O9 . 1.3680(16) yes
N8 . C10 . 1.389(2) yes
O9 . H91 . 0.847 no
C10 . C11 . 1.371(3) yes
C10 . C14 . 1.483(2) yes
C11 . N12 . 1.373(2) yes
C11 . C13 . 1.487(2) yes
N12 . H121 . 0.843 no
C13 . H133 . 0.953 no
C13 . H132 . 0.944 no
C13 . H131 . 0.945 no
C14 . O15 . 1.210(2) yes
C14 . C16 . 1.502(2) yes
C16 . H163 . 0.977 no
C16 . H162 . 0.991 no
C16 . H161 . 0.978 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . P1 . O3 . 107.92(7) yes
O2 . P1 . O4 . 113.16(7) yes
O3 . P1 . O4 . 110.89(8) yes
O2 . P1 . C5 . 111.29(8) yes
O3 . P1 . C5 . 104.77(7) yes
O4 . P1 . C5 . 108.49(7) yes
P1 . O3 . H31 . 121.1 no
P1 . C5 . C6 . 114.10(10) yes
P1 . C5 . H51 . 111.5 no
C6 . C5 . H51 . 108.0 no
P1 . C5 . H52 . 106.1 no
C6 . C5 . H52 . 111.2 no
H51 . C5 . H52 . 105.6 no
C5 . C6 . C7 . 109.63(13) yes
C5 . C6 . H62 . 111.0 no
C7 . C6 . H62 . 107.4 no
C5 . C6 . H61 . 110.1 no
C7 . C6 . H61 . 106.8 no
H62 . C6 . H61 . 111.7 no
C6 . C7 . N8 . 126.89(15) yes
C6 . C7 . N12 . 126.68(16) yes
N8 . C7 . N12 . 106.29(14) yes
C7 . N8 . O9 . 123.06(14) yes
C7 . N8 . C10 . 110.85(13) yes
O9 . N8 . C10 . 125.93(14) yes
N8 . O9 . H91 . 103.3 no
N8 . C10 . C11 . 105.65(14) yes
N8 . C10 . C14 . 126.41(16) yes
C11 . C10 . C14 . 127.56(16) yes
C10 . C11 . N12 . 106.53(15) yes
C10 . C11 . C13 . 132.20(15) yes
N12 . C11 . C13 . 121.26(15) yes
C11 . N12 . C7 . 110.67(13) yes
C11 . N12 . H121 . 126.9 no
C7 . N12 . H121 . 122.4 no
C11 . C13 . H133 . 109.6 no
C11 . C13 . H132 . 108.5 no
H133 . C13 . H132 . 109.8 no
C11 . C13 . H131 . 107.1 no
H133 . C13 . H131 . 111.8 no
H132 . C13 . H131 . 110.0 no
C10 . C14 . O15 . 118.00(16) yes
C10 . C14 . C16 . 119.82(16) yes
O15 . C14 . C16 . 122.12(17) yes
C14 . C16 . H163 . 108.0 no
C14 . C16 . H162 . 110.5 no
H163 . C16 . H162 . 110.6 no
C14 . C16 . H161 . 109.8 no
H163 . C16 . H161 . 109.9 no
H162 . C16 . H161 . 107.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O3 . H31 . O2 1_655 173.49(6) 0.853 1.736 2.585(2) yes
O9 . H91 . O4 2_565 169.39(6) 0.847 1.613 2.451(2) yes
N12 . H121 . O2 2_564 165.98(5) 0.843 1.824 2.649(2) yes
C13 . H131 . O15 2_454 176.51(5) 0.945 2.581 3.524(2) yes
C5 . H51 . O4 2_565 145.24(5) 0.990 2.404 3.267(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/09/13 at 16:40:13
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE O   (   9,X'S) H   (  91,X'S) 
RIDE N   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 133,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  16,X'S) H   ( 163,X'S) H   ( 162,X'S) H   ( 161,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/09/13 at 16:40:13
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 1 -1 x .
0 1 1 x .
0 2 0 x .

_database_code_depnum_ccdc_archive 'CCDC 959100'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1


_cell_length_a                   6.6374(3)
_cell_length_b                   24.5838(15)
_cell_length_c                   7.9643(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.181(5)
_cell_angle_gamma                90
_cell_volume                     1274.89(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ' -P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4


_chemical_formula_sum            'C9 H17 N2 O7 P'
_chemical_formula_moiety         'C9 H15 N2 O6 P, H2 O'
_chemical_compound_source        ?
_chemical_formula_weight         296.22


_cell_measurement_reflns_used    3761
_cell_measurement_theta_min      2.6062
_cell_measurement_theta_max      29.0134
_cell_measurement_temperature    173

_exptl_crystal_description       batonnet
_exptl_crystal_colour            'white transparent'
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.248


_exptl_absorpt_correction_T_min  0.85274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.38 (release 17-11-2008 CrysAlis171 .NET)
(compiled Nov 17 2008,13:58:09)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'

_diffrn_detector_area_resol_mean 8.4205
_diffrn_orient_matrix_UB_11      -0.0104976784
_diffrn_orient_matrix_UB_12      0.0247887792
_diffrn_orient_matrix_UB_13      -0.0461953169
_diffrn_orient_matrix_UB_21      0.0155247125
_diffrn_orient_matrix_UB_22      0.0147003876
_diffrn_orient_matrix_UB_23      0.0779698265
_diffrn_orient_matrix_UB_31      0.1071285841
_diffrn_orient_matrix_UB_32      0.0003446272
_diffrn_orient_matrix_UB_33      0.0020858556

_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.051
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.77
_montpellier_reflns_completeness_maxres 99.9
#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
1 100.0 10.000 0.0 0.0
2 10.000 5.000 93.3 82.4
3 5.000 3.333 100.0 93.8
4 3.333 2.500 100.0 97.3
5 2.500 2.000 100.0 98.5
6 2.000 1.667 100.0 99.1
7 1.667 1.429 100.0 99.4
8 1.429 1.250 100.0 99.6
9 1.250 1.111 100.0 99.7
10 1.111 1.000 100.0 99.8
11 1.000 0.909 100.0 99.8
12 0.909 0.833 100.0 99.9
13 0.833 0.769 96.5 99.2
14 0.769 0.731 43.2 91.6
loop_
_diffrn_reflns_class_number
_diffrn_reflns_class_d_res_high
_diffrn_reflns_class_d_res_low
_diffrn_reflns_class_av_R_eq
_diffrn_reflns_class_av_uI/I
20 0.75 0.73 0.800 1.0
19 0.77 0.75 0.515 1.8
18 0.79 0.77 0.424 2.7
17 0.82 0.79 0.504 3.4
16 0.84 0.82 0.436 4.2
15 0.87 0.84 0.445 4.2
14 0.91 0.87 0.308 6.0
13 0.94 0.91 0.276 6.7
12 0.99 0.94 0.221 9.0
11 1.03 0.99 0.180 10.2
10 1.09 1.03 0.118 16.9
9 1.16 1.09 0.099 21.3
8 1.24 1.16 0.100 20.8
7 1.34 1.24 0.083 26.9
6 1.46 1.34 0.056 41.4
5 1.64 1.46 0.060 40.2
4 1.89 1.64 0.041 57.9
3 2.31 1.89 0.035 76.5
2 3.27 2.31 0.024 946
1 100.0 3.27 0.018 577
_diffrn_measurement_method       ω


_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.38 (release 17-11-2008 CrysAlis171 .NET)
(compiled Nov 17 2008,13:58:09)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.38 (release 17-11-2008 CrysAlis171 .NET)
(compiled Nov 17 2008,13:58:09)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.38 (release 17-11-2008 CrysAlis171 .NET)
(compiled Nov 17 2008,13:58:09)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00  116.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864   77.0000  120.0000    0.0000    0.0000 135

#__ type_ start__ end____ width___ exp.time_
  2 omega  -71.00   -7.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864  -45.0000  300.0000    0.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   43.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864   45.0000  180.0000    0.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00   20.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864    0.0000  180.0000    0.0000    0.0000 99

#__ type_ start__ end____ width___ exp.time_
  5 omega  -79.00  -11.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864    0.0000   60.0000    0.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -15.00   49.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864   45.0000   30.0000    0.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  -11.00   52.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864  -45.0000  330.0000    0.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
  8 omega  -14.00   48.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864   45.0000  270.0000    0.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  9 omega  -12.00   56.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864  -77.0000  210.0000    0.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega  -11.00   50.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864  -45.0000   90.0000    0.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 11 omega   -4.00   54.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       19.0864  -77.0000   90.0000    0.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega  -52.00   16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -22.6020  -77.0000  270.0000    0.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
 13 omega  -53.00    8.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -22.6020   77.0000  330.0000    0.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega  -45.00  -15.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -22.6020  -45.0000  330.0000    0.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega -114.00  -87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -22.6020    0.0000  150.0000    0.0000    0.0000 27

;

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      173
_diffrn_reflns_number            23995
_reflns_number_total             3110
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections with Friedels Law is 3110
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 3404 


_diffrn_reflns_theta_min         2.735
_diffrn_reflns_theta_max         29.074
_diffrn_measured_fraction_theta_max 0.913

_diffrn_reflns_theta_full        26.748
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -9
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              33
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   1.33
_oxford_diffrn_Wilson_scale      1.53

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom


_refine_diff_density_min         -0.41
_refine_diff_density_max         0.34


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1528
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0382
_refine_ls_wR_factor_ref         0.0377
_refine_ls_goodness_of_fit_ref   1.0790
_refine_ls_shift/su_max          0.000308


# The values computed from all data 
_oxford_reflns_number_all        3110
_refine_ls_R_factor_all          0.1130
_refine_ls_wR_factor_all         0.0616

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1528
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.0377

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]²
 Ai are: 
 1.93 -1.10 1.30 -0.169
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
P1 P 0.66756(11) 0.26615(3) 0.64556(9) 0.0162 1.0000 Uani . . . . . . .
O2 O 0.8389(3) 0.22981(10) 0.7513(3) 0.0308 1.0000 Uani . . . . . . .
H3 H 0.9005 0.2452 0.8374 0.0500 1.0000 Uiso R . . . . . .
O4 O 0.7553(3) 0.31040(9) 0.5493(2) 0.0252 1.0000 Uani . . . . . . .
O5 O 0.5161(3) 0.22949(9) 0.5329(2) 0.0200 1.0000 Uani . . . . . . .
C6 C 0.5453(4) 0.29784(13) 0.8030(3) 0.0188 1.0000 Uani . . . . . . .
C7 C 0.3595(4) 0.33184(13) 0.7216(3) 0.0211 1.0000 Uani . . . . . . .
C8 C 0.2628(4) 0.35863(12) 0.8527(3) 0.0159 1.0000 Uani . . . . . . .
N9 N 0.0820(3) 0.38292(9) 0.8243(3) 0.0143 1.0000 Uani . . . . . . .
O10 O -0.0313(3) 0.39066(8) 0.6627(2) 0.0208 1.0000 Uani . . . . . . .
H11 H -0.1189 0.3590 0.6295 0.0500 1.0000 Uiso R . . . . . .
C12 C 0.0428(4) 0.40540(11) 0.9758(3) 0.0164 1.0000 Uani . . . . . . .
C13 C 0.2079(4) 0.39272(11) 1.0993(3) 0.0160 1.0000 Uani . . . . . . .
N14 N 0.3411(3) 0.36412(10) 1.0205(3) 0.0149 1.0000 Uani . . . . . . .
H15 H 0.4668 0.3475 1.0699 0.0500 1.0000 Uiso R . . . . . .
C16 C 0.2543(5) 0.40308(14) 1.2869(3) 0.0236 1.0000 Uani . . . . . . .
H17 H 0.3828 0.3861 1.3346 0.0500 1.0000 Uiso R . . . . . .
H18 H 0.1475 0.3879 1.3380 0.0500 1.0000 Uiso R . . . . . .
H19 H 0.2624 0.4418 1.3087 0.0500 1.0000 Uiso R . . . . . .
C20 C -0.1479(4) 0.43419(12) 0.9867(4) 0.0178 1.0000 Uani . . . . . . .
O21 O -0.1236(3) 0.46011(8) 1.1365(3) 0.0207 1.0000 Uani . . . . . . .
C22 C -0.3089(4) 0.48423(14) 1.1772(4) 0.0237 1.0000 Uani . . . . . . .
C23 C -0.2687(5) 0.49737(15) 1.3645(4) 0.0306 1.0000 Uani . . . . . . .
H24 H -0.3884 0.5154 1.3899 0.0500 1.0000 Uiso R . . . . . .
H25 H -0.1511 0.5216 1.3922 0.0500 1.0000 Uiso R . . . . . .
H26 H -0.2434 0.4640 1.4300 0.0500 1.0000 Uiso R . . . . . .
H27 H -0.3419 0.5170 1.1101 0.0267 1.0000 Uiso R . . . . . .
H28 H -0.4237 0.4587 1.1490 0.0267 1.0000 Uiso R . . . . . .
O29 O -0.3032(3) 0.43343(10) 0.8804(3) 0.0285 1.0000 Uani . . . . . . .
H30 H 0.4030 0.3592 0.6476 0.0262 1.0000 Uiso R . . . . . .
H31 H 0.2569 0.3083 0.6546 0.0262 1.0000 Uiso R . . . . . .
H32 H 0.6445 0.3212 0.8751 0.0220 1.0000 Uiso R . . . . . .
H33 H 0.5024 0.2697 0.8729 0.0220 1.0000 Uiso R . . . . . .
O34 O 0.2353(3) 0.16453(9) 0.7003(2) 0.0244 1.0000 Uani . . . . . . .
H35 H 0.2419 0.1712 0.8131 0.0500 1.0000 Uiso R . . . . . .
H36 H 0.3319 0.1844 0.6623 0.0500 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0140(3) 0.0228(4) 0.0102(3) -0.0036(3) -0.0016(2) 0.0047(3)
O2 0.0278(11) 0.0386(14) 0.0195(10) -0.0136(10) -0.0119(8) 0.0177(11)
O4 0.0247(11) 0.0369(14) 0.0139(9) -0.0071(9) 0.0037(8) -0.0095(10)
O5 0.0211(10) 0.0215(11) 0.0141(9) -0.0033(9) -0.0046(8) 0.0021(9)
C6 0.0212(15) 0.0233(16) 0.0116(12) -0.0012(12) 0.0025(11) 0.0073(12)
C7 0.0206(14) 0.0269(18) 0.0153(13) -0.0015(12) 0.0023(11) 0.0081(12)
C8 0.0153(12) 0.0190(16) 0.0136(12) 0.0015(11) 0.0034(11) -0.0024(11)
N9 0.0140(11) 0.0161(12) 0.0116(10) 0.0007(9) 0.0001(8) 0.0012(9)
O10 0.0206(10) 0.0249(12) 0.0136(9) 0.0023(8) -0.0050(8) 0.0007(9)
C12 0.0196(14) 0.0152(15) 0.0151(12) -0.0060(11) 0.0049(10) -0.0030(12)
C13 0.0172(13) 0.0156(15) 0.0160(12) -0.0014(11) 0.0050(10) -0.0022(11)
N14 0.0141(11) 0.0173(13) 0.0134(10) 0.0015(9) 0.0029(9) 0.0019(9)
C16 0.0214(14) 0.0338(19) 0.0154(14) -0.0036(13) 0.0034(12) 0.0046(14)
C20 0.0179(13) 0.0165(15) 0.0192(13) 0.0014(12) 0.0036(11) -0.0013(11)
O21 0.0141(10) 0.0242(12) 0.0238(10) -0.0064(9) 0.0040(8) 0.0028(9)
C22 0.0176(15) 0.0264(17) 0.0279(17) -0.0011(13) 0.0061(13) 0.0022(13)
C23 0.0291(17) 0.037(2) 0.0261(15) -0.0062(15) 0.0069(13) 0.0018(16)
O29 0.0181(11) 0.0393(14) 0.0256(11) -0.0064(10) -0.0017(9) 0.0073(10)
O34 0.0219(10) 0.0329(13) 0.0175(9) -0.0040(9) 0.0016(8) -0.0042(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.8027(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . O2 . 1.559(2) yes
P1 . O4 . 1.511(2) yes
P1 . O5 . 1.509(2) yes
P1 . C6 . 1.798(3) yes
O2 . H3 . 0.819 no
C6 . C7 . 1.526(4) yes
C6 . H32 . 0.973 no
C6 . H33 . 0.965 no
C7 . C8 . 1.482(4) yes
C7 . H30 . 0.975 no
C7 . H31 . 0.971 no
C8 . N9 . 1.320(4) yes
C8 . N14 . 1.343(3) yes
N9 . O10 . 1.372(3) yes
N9 . C12 . 1.396(3) yes
O10 . H11 . 0.977 no
C12 . C13 . 1.360(4) yes
C12 . C20 . 1.468(4) yes
C13 . N14 . 1.373(3) yes
C13 . C16 . 1.488(4) yes
N14 . H15 . 0.944 no
C16 . H17 . 0.960 no
C16 . H18 . 0.959 no
C16 . H19 . 0.967 no
C20 . O21 . 1.335(3) yes
C20 . O29 . 1.200(3) yes
O21 . C22 . 1.457(3) yes
C22 . C23 . 1.499(4) yes
C22 . H27 . 0.968 no
C22 . H28 . 0.979 no
C23 . H24 . 0.965 no
C23 . H25 . 0.973 no
C23 . H26 . 0.970 no
O34 . H35 . 0.906 no
O34 . H36 . 0.904 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . P1 . O4 . 111.98(13) yes
O2 . P1 . O5 . 108.13(12) yes
O4 . P1 . O5 . 113.94(11) yes
O2 . P1 . C6 . 104.60(12) yes
O4 . P1 . C6 . 108.21(14) yes
O5 . P1 . C6 . 109.56(13) yes
P1 . O2 . H3 . 112.4 no
P1 . C6 . C7 . 112.22(18) yes
P1 . C6 . H32 . 108.8 no
C7 . C6 . H32 . 109.0 no
P1 . C6 . H33 . 108.4 no
C7 . C6 . H33 . 109.5 no
H32 . C6 . H33 . 108.9 no
C6 . C7 . C8 . 111.7(2) yes
C6 . C7 . H30 . 109.0 no
C8 . C7 . H30 . 109.8 no
C6 . C7 . H31 . 109.2 no
C8 . C7 . H31 . 107.4 no
H30 . C7 . H31 . 109.7 no
C7 . C8 . N9 . 125.7(2) yes
C7 . C8 . N14 . 127.5(2) yes
N9 . C8 . N14 . 106.8(2) yes
C8 . N9 . O10 . 122.6(2) yes
C8 . N9 . C12 . 110.3(2) yes
O10 . N9 . C12 . 126.5(2) yes
N9 . O10 . H11 . 109.4 no
N9 . C12 . C13 . 106.0(2) yes
N9 . C12 . C20 . 123.3(2) yes
C13 . C12 . C20 . 130.6(2) yes
C12 . C13 . N14 . 106.7(2) yes
C12 . C13 . C16 . 131.9(3) yes
N14 . C13 . C16 . 121.4(2) yes
C13 . N14 . C8 . 110.3(2) yes
C13 . N14 . H15 . 128.8 no
C8 . N14 . H15 . 120.8 no
C13 . C16 . H17 . 108.5 no
C13 . C16 . H18 . 109.5 no
H17 . C16 . H18 . 109.6 no
C13 . C16 . H19 . 110.0 no
H17 . C16 . H19 . 110.0 no
H18 . C16 . H19 . 109.1 no
C12 . C20 . O21 . 109.1(2) yes
C12 . C20 . O29 . 125.7(3) yes
O21 . C20 . O29 . 125.2(3) yes
C20 . O21 . C22 . 115.6(2) yes
O21 . C22 . C23 . 108.3(2) yes
O21 . C22 . H27 . 109.1 no
C23 . C22 . H27 . 110.3 no
O21 . C22 . H28 . 109.9 no
C23 . C22 . H28 . 110.3 no
H27 . C22 . H28 . 108.9 no
C22 . C23 . H24 . 108.2 no
C22 . C23 . H25 . 109.7 no
H24 . C23 . H25 . 109.2 no
C22 . C23 . H26 . 109.4 no
H24 . C23 . H26 . 109.9 no
H25 . C23 . H26 . 110.4 no
H35 . O34 . H36 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O2 . H3 . O5 3_555 172 0.82 1.71 2.528(4) yes
O10 . H11 . O4 1_455 171 0.98 1.52 2.494(4) yes
N14 . H15 . O34 3_555 162 0.94 1.90 2.818(4) yes
C23 . H25 . O10 2_567 150 0.97 2.55 3.429(4) yes
C6 . H32 . O34 3_555 133 0.97 2.57 3.303(4) yes
O34 . H35 . O4 3_455 177 0.91 1.92 2.825(4) yes
O34 . H36 . O5 . 170 0.90 2.07 2.961(4) yes

_database_code_depnum_ccdc_archive 'CCDC 959101'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          ?
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or
# _oxford_atom_site_special_shape

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.8726(2)
_cell_length_b                   10.7546(3)
_cell_length_c                   14.0957(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.274(3)
_cell_angle_gamma                90
_cell_volume                     1183.83(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C8 N1.60 O4 P0.80 
# Dc =      1.45 Fooo =    568.00 Mu =      2.46 M =    259.09
# Found Formula = C8 H10.40 N1.60 O4 P0.80 
# Dc =      1.53 FOOO =    568.00 Mu =      2.48 M =    272.20

_chemical_formula_sum            'C10 H13 N2 O5 P'
_chemical_formula_moiety         'C10 H13 N2 O5 P'
_chemical_compound_source        ?
_chemical_formula_weight         272.19


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.248

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      175
_diffrn_reflns_number            11529
_reflns_number_total             2834
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 2834 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 3145 


_diffrn_reflns_theta_min         2.914
_diffrn_reflns_theta_max         28.992
_diffrn_measured_fraction_theta_max 0.900

_diffrn_reflns_theta_full        25.223
_diffrn_measured_fraction_theta_full 0.983


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.11
_oxford_diffrn_Wilson_scale      0.92

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.34
_refine_diff_density_max         0.29


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0358
_refine_ls_wR_factor_ref         0.0360
_refine_ls_goodness_of_fit_ref   1.0692
_refine_ls_shift/su_max          0.0002687
_refine_ls_shift/su_mean         0.0000337


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2833
_refine_ls_R_factor_all          0.0728
_refine_ls_wR_factor_all         0.0486

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1751
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0360

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.50 -1.07 0.922 -0.400 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.18441(7) 0.52924(5) 0.62543(4) 0.0237 1.0000 Uani . . . . . .
O2 O 0.00591(19) 0.46595(16) 0.62771(11) 0.0355 1.0000 Uani . . . . . .
H3 H -0.0616 0.4532 0.5724 0.0500 1.0000 Uiso R . . . . .
O4 O 0.19571(18) 0.58366(14) 0.52759(11) 0.0291 1.0000 Uani . . . . . .
O5 O 0.2140(2) 0.61866(14) 0.70737(11) 0.0318 1.0000 Uani . . . . . .
C6 C 0.3390(3) 0.4052(2) 0.64539(15) 0.0278 1.0000 Uani . . . . . .
C7 C 0.3367(3) 0.3193(2) 0.55852(15) 0.0266 1.0000 Uani . . . . . .
C8 C 0.4740(3) 0.22410(19) 0.57190(14) 0.0231 1.0000 Uani . . . . . .
N9 N 0.6361(2) 0.23826(16) 0.55558(12) 0.0238 1.0000 Uani . . . . . .
C10 C 0.7276(3) 0.1308(2) 0.57755(15) 0.0241 1.0000 Uani . . . . . .
C11 C 0.6171(2) 0.04731(19) 0.60952(14) 0.0230 1.0000 Uani . . . . . .
N12 N 0.4619(2) 0.10988(16) 0.60546(12) 0.0221 1.0000 Uani . . . . . .
O13 O 0.31136(17) 0.05846(14) 0.62557(11) 0.0284 1.0000 Uani . . . . . .
H14 H 0.2967 0.0786 0.6916 0.0500 1.0000 Uiso R . . . . .
C15 C 0.6400(3) -0.0798(2) 0.64271(15) 0.0258 1.0000 Uani . . . . . .
O16 O 0.8062(2) -0.12117(15) 0.65250(13) 0.0366 1.0000 Uani . . . . . .
C17 C 0.8019(4) -0.2421(2) 0.68404(18) 0.0410 1.0000 Uani . . . . . .
C18 C 0.6411(4) -0.2752(2) 0.69264(17) 0.0387 1.0000 Uani . . . . . .
C19 C 0.5353(3) -0.1709(2) 0.66651(16) 0.0322 1.0000 Uani . . . . . .
H20 H 0.4122 -0.1670 0.6651 0.0397 1.0000 Uiso R . . . . .
H21 H 0.6041 -0.3524 0.7155 0.0463 1.0000 Uiso R . . . . .
H22 H 0.9022 -0.2904 0.6970 0.0487 1.0000 Uiso R . . . . .
C23 C 0.9127(3) 0.1251(2) 0.56751(19) 0.0372 1.0000 Uani . . . . . .
H24 H 0.9580 0.0440 0.5832 0.0583 1.0000 Uiso R . . . . .
H25 H 0.9751 0.1862 0.6105 0.0584 1.0000 Uiso R . . . . .
H26 H 0.9258 0.1465 0.5019 0.0580 1.0000 Uiso R . . . . .
H27 H 0.6837 0.3077 0.5203 0.0500 1.0000 Uiso R . . . . .
H28 H 0.3496 0.3678 0.5001 0.0312 1.0000 Uiso R . . . . .
H29 H 0.2271 0.2758 0.5475 0.0314 1.0000 Uiso R . . . . .
H30 H 0.4534 0.4402 0.6591 0.0344 1.0000 Uiso R . . . . .
H31 H 0.3111 0.3561 0.7020 0.0341 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0231(2) 0.0235(3) 0.0256(3) 0.0039(2) 0.00763(19) 0.0025(2)
O2 0.0290(8) 0.0463(10) 0.0320(8) 0.0098(8) 0.0072(6) -0.0063(7)
O4 0.0264(7) 0.0307(8) 0.0308(8) 0.0082(7) 0.0060(6) -0.0023(6)
O5 0.0356(8) 0.0272(8) 0.0352(9) -0.0032(7) 0.0143(7) 0.0018(7)
C6 0.0286(11) 0.0285(11) 0.0260(11) -0.0011(9) 0.0026(9) 0.0080(9)
C7 0.0261(10) 0.0277(11) 0.0256(11) -0.0004(9) 0.0013(8) 0.0041(8)
C8 0.0240(9) 0.0260(10) 0.0196(10) -0.0036(8) 0.0043(8) 0.0001(8)
N9 0.0223(8) 0.0248(9) 0.0257(9) -0.0002(7) 0.0084(7) -0.0033(7)
C10 0.0235(10) 0.0251(10) 0.0242(10) -0.0028(8) 0.0054(8) 0.0007(8)
C11 0.0213(9) 0.0247(10) 0.0231(10) -0.0045(8) 0.0038(7) -0.0001(8)
N12 0.0178(8) 0.0244(9) 0.0249(9) -0.0017(7) 0.0052(7) -0.0017(7)
O13 0.0183(7) 0.0351(8) 0.0327(8) -0.0013(7) 0.0070(6) -0.0065(6)
C15 0.0277(10) 0.0256(10) 0.0234(10) -0.0043(8) 0.0013(8) 0.0020(8)
O16 0.0322(8) 0.0303(9) 0.0459(10) 0.0010(8) -0.0003(7) 0.0070(7)
C17 0.0539(16) 0.0273(12) 0.0389(14) -0.0016(10) -0.0058(11) 0.0114(11)
C18 0.0605(16) 0.0257(12) 0.0286(12) 0.0003(10) 0.0010(11) -0.0006(11)
C19 0.0428(13) 0.0255(11) 0.0289(12) -0.0032(9) 0.0071(10) -0.0034(10)
C23 0.0260(11) 0.0369(13) 0.0516(15) 0.0007(12) 0.0156(11) 0.0006(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.0700(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . O2 . 1.5655(16) yes
P1 . O4 . 1.5111(15) yes
P1 . O5 . 1.4985(16) yes
P1 . C6 . 1.804(2) yes
O2 . H3 . 0.897 no
C6 . C7 . 1.532(3) yes
C6 . H30 . 0.972 no
C6 . H31 . 1.004 no
C7 . C8 . 1.484(3) yes
C7 . H28 . 0.991 no
C7 . H29 . 0.976 no
C8 . N9 . 1.334(3) yes
C8 . N12 . 1.324(3) yes
N9 . C10 . 1.376(3) yes
N9 . H27 . 0.997 no
C10 . C11 . 1.365(3) yes
C10 . C23 . 1.484(3) yes
C11 . N12 . 1.390(3) yes
C11 . C15 . 1.448(3) yes
N12 . O13 . 1.370(2) yes
O13 . H14 . 0.976 no
C15 . O16 . 1.373(3) yes
C15 . C19 . 1.350(3) yes
O16 . C17 . 1.377(3) yes
C17 . C18 . 1.335(4) yes
C17 . H22 . 0.943 no
C18 . C19 . 1.418(3) yes
C18 . H21 . 0.950 no
C19 . H20 . 0.967 no
C23 . H24 . 0.958 no
C23 . H25 . 0.982 no
C23 . H26 . 0.971 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . P1 . O4 . 110.12(9) yes
O2 . P1 . O5 . 108.40(9) yes
O4 . P1 . O5 . 115.69(9) yes
O2 . P1 . C6 . 105.36(10) yes
O4 . P1 . C6 . 108.20(9) yes
O5 . P1 . C6 . 108.57(10) yes
P1 . O2 . H3 . 118.9 no
P1 . C6 . C7 . 112.41(15) yes
P1 . C6 . H30 . 109.5 no
C7 . C6 . H30 . 108.1 no
P1 . C6 . H31 . 107.5 no
C7 . C6 . H31 . 109.7 no
H30 . C6 . H31 . 109.7 no
C6 . C7 . C8 . 112.29(17) yes
C6 . C7 . H28 . 110.8 no
C8 . C7 . H28 . 108.6 no
C6 . C7 . H29 . 109.7 no
C8 . C7 . H29 . 107.7 no
H28 . C7 . H29 . 107.6 no
C7 . C8 . N9 . 126.66(19) yes
C7 . C8 . N12 . 126.97(18) yes
N9 . C8 . N12 . 106.34(18) yes
C8 . N9 . C10 . 110.48(17) yes
C8 . N9 . H27 . 126.9 no
C10 . N9 . H27 . 121.5 no
N9 . C10 . C11 . 106.85(17) yes
N9 . C10 . C23 . 120.34(19) yes
C11 . C10 . C23 . 132.8(2) yes
C10 . C11 . N12 . 105.15(18) yes
C10 . C11 . C15 . 131.99(19) yes
N12 . C11 . C15 . 122.86(18) yes
C11 . N12 . C8 . 111.17(16) yes
C11 . N12 . O13 . 125.13(16) yes
C8 . N12 . O13 . 123.49(16) yes
N12 . O13 . H14 . 108.5 no
C11 . C15 . O16 . 114.59(18) yes
C11 . C15 . C19 . 135.3(2) yes
O16 . C15 . C19 . 110.11(19) yes
C15 . O16 . C17 . 106.05(19) yes
O16 . C17 . C18 . 110.1(2) yes
O16 . C17 . H22 . 121.9 no
C18 . C17 . H22 . 128.0 no
C17 . C18 . C19 . 107.3(2) yes
C17 . C18 . H21 . 126.8 no
C19 . C18 . H21 . 125.8 no
C18 . C19 . C15 . 106.4(2) yes
C18 . C19 . H20 . 126.4 no
C15 . C19 . H20 . 127.2 no
C10 . C23 . H24 . 110.9 no
C10 . C23 . H25 . 109.5 no
H24 . C23 . H25 . 108.9 no
C10 . C23 . H26 . 107.8 no
H24 . C23 . H26 . 110.8 no
H25 . C23 . H26 . 108.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O2 . H3 . O4 2_566 174.52(7) 0.897 1.697 2.592(3) yes
O13 . H14 . O5 4_546 174.82(8) 0.976 1.501 2.475(3) yes
C23 . H24 . O16 . 125.10(7) 0.958 2.415 3.067(3) yes
N9 . H27 . O4 2_666 168.09(8) 0.997 1.698 2.681(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/09/13 at 16:57:22
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE O   (   2,X'S) H   (   3,X'S) 
RIDE C   (   6,X'S) H   (  30,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  28,X'S) H   (  29,X'S) 
RIDE N   (   9,X'S) H   (  27,X'S) 
RIDE O   (  13,X'S) H   (  14,X'S) 
RIDE C   (  17,X'S) H   (  22,X'S) 
RIDE C   (  18,X'S) H   (  21,X'S) 
RIDE C   (  19,X'S) H   (  20,X'S) 
RIDE C   (  23,X'S) H   (  24,X'S) H   (  25,X'S) H   (  26,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/09/13 at 16:57:22
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 0 x .

_database_code_depnum_ccdc_archive 'CCDC 959102'
