# Electronic Supplementary Material (ESI) for ChemComm.
# 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
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#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_21
#==============================================================================
_audit_creation_date             14-07-04
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 010jr11
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   5.5980(1)
_cell_length_b                   13.2848(3)
_cell_length_c                   14.6114(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1086.63(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,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'


_cell_formula_units_Z            4

# Given Formula = C10 H15 N1 O5 
# Dc =      1.40 Fooo =    488.00 Mu =      1.13 M =    229.23
# Found Formula = C10 H15 N1 O5 
# Dc =      1.40 FOOO =    488.00 Mu =      1.13 M =    229.23

_chemical_formula_sum            'C10 H15 N1 O5'
_chemical_formula_moiety         'C10 H15 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         229.23


_cell_measurement_reflns_used    1464
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.26
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_max          0.38

_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.113

# Sheldrick geometric approximatio 0.96 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.97
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      150
_diffrn_reflns_number            15474
_reflns_number_total             1449
_diffrn_reflns_av_R_equivalents  0.011
# Number of reflections without Friedels Law is 2468 
# Number of reflections with Friedels Law is 1449 
# Theoretical number of reflections is about 1242 

_refine_special_details          
; 
 No of Reflections processed =   2467
 No of Friedel Pairs found =     1019 No of Friedel Pairs used  =     1019
 No of Unpaired Reflections  =      1
 No of Centric Reflections   =    428
 
 Flack parameter obtained from original refinemen
 Hooft parameter obtained with Flack x set to zero

 Friedif =       6.80     Acta A63, (2007), 257-265
 Estimated Friedel difference =     0.2534
                                                                               
 Flack & Shmueli (2007) recommend a value >200
 for general structures and >80 for enantiopure crystals

 Flack Parameter & su    0.1692    0.8157
 Hooft Parameter & su   -0.1148    0.3549
           Ton G & su    1.2295    0.7097

The absolute configuration has not been reliably determined

 For an enantiopure material, there are 2 choices, P2
 P2(correct)     0.9925   i.e. 0.992471E+00

 If 50:50 twinning is possible, there are 3 choices, P3
 P3(correct)     0.8048   i.e. 0.804803E+00                                      
 P3(rac-twin)    0.1891   i.e. 0.189092E+00                                      
 P3(inverse)     0.0061   i.e. 0.610549E-02                                      
 G               1.2295                                                          
 G S.U.          0.7097                                                          
 FLEQ           -0.1148                                                           
 FLEQ S.U.       0.3549   i.e. 0.354869E+00

 Restrained Flack x = -0.083(268)
;


_diffrn_reflns_theta_min         5.191
_diffrn_reflns_theta_max         27.450
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        27.450
_diffrn_measured_fraction_theta_full 0.989


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              0
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.63
_oxford_diffrn_Wilson_scale      0.62

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

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.15


# 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         1448
_refine_ls_number_restraints     0
_refine_ls_number_parameters     145
_oxford_refine_ls_R_factor_ref   0.0300
_refine_ls_wR_factor_ref         0.0704
_refine_ls_goodness_of_fit_ref   0.9429
_refine_ls_shift/su_max          0.0002744
_refine_ls_shift/su_mean         0.0000323


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1448
_refine_ls_R_factor_all          0.0300
_refine_ls_wR_factor_all         0.0704

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1350
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_gt          0.0661

# 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 unk


_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: 
 26.7 43.0 25.6 11.1 2.67 
;

# 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
O1 O 0.2110(2) 0.52966(8) 0.35424(7) 0.0317 1.0000 Uani . . . . . .
C2 C 0.2390(3) 0.59506(11) 0.27694(11) 0.0317 1.0000 Uani . . . . . .
C3 C 0.1196(3) 0.54106(11) 0.19788(10) 0.0274 1.0000 Uani . . . . . .
O4 O 0.2832(2) 0.47291(8) 0.15500(8) 0.0309 1.0000 Uani . . . . . .
C5 C 0.1632(3) 0.37892(11) 0.14322(10) 0.0275 1.0000 Uani . . . . . .
C6 C 0.0214(4) 0.37807(15) 0.05462(11) 0.0420 1.0000 Uani . . . . . .
C7 C 0.3462(4) 0.29583(13) 0.15015(14) 0.0420 1.0000 Uani . . . . . .
O8 O 0.0061(2) 0.37186(8) 0.21936(7) 0.0271 1.0000 Uani . . . . . .
C9 C -0.0647(3) 0.47138(11) 0.24411(10) 0.0250 1.0000 Uani . . . . . .
C10 C -0.0248(3) 0.48929(10) 0.34659(10) 0.0253 1.0000 Uani . . . . . .
C11 C -0.0387(3) 0.39548(10) 0.40484(10) 0.0243 1.0000 Uani . . . . . .
C12 C -0.2790(3) 0.34215(13) 0.39885(10) 0.0333 1.0000 Uani . . . . . .
O13 O -0.3203(2) 0.30390(9) 0.49065(7) 0.0323 1.0000 Uani . . . . . .
C14 C -0.1688(3) 0.35083(11) 0.54925(10) 0.0254 1.0000 Uani . . . . . .
O15 O -0.1721(2) 0.33334(8) 0.63093(7) 0.0326 1.0000 Uani . . . . . .
N16 N -0.0321(3) 0.41664(9) 0.50280(8) 0.0267 1.0000 Uani . . . . . .
H21 H 0.1586 0.6602 0.2892 0.0386 1.0000 Uiso R . . . . .
H22 H 0.4102 0.6088 0.2657 0.0377 1.0000 Uiso R . . . . .
H31 H 0.0486 0.5871 0.1514 0.0328 1.0000 Uiso R . . . . .
H61 H -0.0611 0.3133 0.0501 0.0623 1.0000 Uiso R . . . . .
H63 H -0.0912 0.4345 0.0558 0.0624 1.0000 Uiso R . . . . .
H62 H 0.1297 0.3857 0.0029 0.0634 1.0000 Uiso R . . . . .
H71 H 0.2691 0.2304 0.1397 0.0625 1.0000 Uiso R . . . . .
H72 H 0.4218 0.2975 0.2110 0.0629 1.0000 Uiso R . . . . .
H73 H 0.4682 0.3063 0.1037 0.0634 1.0000 Uiso R . . . . .
H91 H -0.2277 0.4861 0.2242 0.0293 1.0000 Uiso R . . . . .
H101 H -0.1390 0.5406 0.3702 0.0292 1.0000 Uiso R . . . . .
H111 H 0.0892 0.3508 0.3872 0.0293 1.0000 Uiso R . . . . .
H122 H -0.4069 0.3893 0.3863 0.0408 1.0000 Uiso R . . . . .
H121 H -0.2759 0.2849 0.3564 0.0404 1.0000 Uiso R . . . . .
H161 H 0.0881 0.4469 0.5293 0.0331 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
O1 0.0347(6) 0.0313(6) 0.0292(5) 0.0022(5) -0.0025(5) -0.0121(5)
C2 0.0400(9) 0.0222(6) 0.0330(8) 0.0007(6) 0.0058(7) -0.0067(7)
C3 0.0298(8) 0.0234(7) 0.0289(7) 0.0058(6) 0.0013(7) -0.0005(6)
O4 0.0303(6) 0.0275(5) 0.0351(6) -0.0051(4) 0.0076(5) -0.0070(5)
C5 0.0314(8) 0.0263(7) 0.0249(7) -0.0010(6) 0.0037(7) -0.0055(6)
C6 0.0531(12) 0.0475(10) 0.0254(7) 0.0012(7) -0.0047(8) -0.0135(10)
C7 0.0416(10) 0.0347(8) 0.0496(10) -0.0106(8) 0.0053(9) 0.0041(8)
O8 0.0342(6) 0.0224(5) 0.0248(5) 0.0007(4) 0.0044(5) -0.0025(5)
C9 0.0225(7) 0.0234(6) 0.0292(7) 0.0032(6) 0.0004(6) 0.0011(6)
C10 0.0262(7) 0.0208(6) 0.0290(7) 0.0008(6) 0.0032(6) -0.0005(6)
C11 0.0280(7) 0.0213(6) 0.0238(7) -0.0004(5) 0.0007(6) -0.0001(6)
C12 0.0400(10) 0.0338(8) 0.0263(7) 0.0035(6) -0.0025(7) -0.0117(8)
O13 0.0321(6) 0.0361(6) 0.0285(5) 0.0052(5) -0.0013(5) -0.0107(5)
C14 0.0255(7) 0.0228(6) 0.0280(7) -0.0011(5) 0.0017(7) 0.0029(6)
O15 0.0389(6) 0.0331(5) 0.0257(5) 0.0016(4) 0.0057(5) 0.0022(5)
N16 0.0315(7) 0.0246(5) 0.0241(6) -0.0011(5) -0.0003(6) -0.0055(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.223(6)
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
O1 . C2 . 1.4335(18) yes
O1 . C10 . 1.4296(18) yes
C2 . C3 . 1.515(2) yes
C2 . H21 . 0.992 no
C2 . H22 . 0.989 no
C3 . O4 . 1.4322(19) yes
C3 . C9 . 1.542(2) yes
C3 . H31 . 0.997 no
O4 . C5 . 1.4284(17) yes
C5 . C6 . 1.518(2) yes
C5 . C7 . 1.509(2) yes
C5 . O8 . 1.4212(18) yes
C6 . H61 . 0.979 no
C6 . H63 . 0.979 no
C6 . H62 . 0.974 no
C7 . H71 . 0.983 no
C7 . H72 . 0.985 no
C7 . H73 . 0.973 no
O8 . C9 . 1.4268(17) yes
C9 . C10 . 1.532(2) yes
C9 . H91 . 0.977 no
C10 . C11 . 1.5111(19) yes
C10 . H101 . 0.996 no
C11 . C12 . 1.523(2) yes
C11 . N16 . 1.4592(18) yes
C11 . H111 . 0.965 no
C12 . O13 . 1.4529(18) yes
C12 . H122 . 0.969 no
C12 . H121 . 0.981 no
O13 . C14 . 1.3570(19) yes
C14 . O15 . 1.2160(19) yes
C14 . N16 . 1.3456(19) yes
N16 . H161 . 0.874 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
C2 . O1 . C10 . 105.47(12) yes
O1 . C2 . C3 . 105.40(12) yes
O1 . C2 . H21 . 109.7 no
C3 . C2 . H21 . 110.5 no
O1 . C2 . H22 . 110.4 no
C3 . C2 . H22 . 112.8 no
H21 . C2 . H22 . 108.0 no
C2 . C3 . O4 . 110.52(14) yes
C2 . C3 . C9 . 104.21(12) yes
O4 . C3 . C9 . 103.89(11) yes
C2 . C3 . H31 . 113.9 no
O4 . C3 . H31 . 110.1 no
C9 . C3 . H31 . 113.6 no
C3 . O4 . C5 . 107.72(12) yes
O4 . C5 . C6 . 110.81(13) yes
O4 . C5 . C7 . 108.17(14) yes
C6 . C5 . C7 . 113.99(15) yes
O4 . C5 . O8 . 104.74(11) yes
C6 . C5 . O8 . 110.09(14) yes
C7 . C5 . O8 . 108.61(13) yes
C5 . C6 . H61 . 108.1 no
C5 . C6 . H63 . 108.4 no
H61 . C6 . H63 . 111.8 no
C5 . C6 . H62 . 109.6 no
H61 . C6 . H62 . 109.5 no
H63 . C6 . H62 . 109.6 no
C5 . C7 . H71 . 109.8 no
C5 . C7 . H72 . 109.6 no
H71 . C7 . H72 . 110.4 no
C5 . C7 . H73 . 109.0 no
H71 . C7 . H73 . 109.1 no
H72 . C7 . H73 . 109.0 no
C5 . O8 . C9 . 108.00(11) yes
C3 . C9 . O8 . 105.04(12) yes
C3 . C9 . C10 . 103.74(12) yes
O8 . C9 . C10 . 110.55(11) yes
C3 . C9 . H91 . 112.0 no
O8 . C9 . H91 . 111.7 no
C10 . C9 . H91 . 113.3 no
C9 . C10 . O1 . 105.61(12) yes
C9 . C10 . C11 . 114.51(12) yes
O1 . C10 . C11 . 108.23(12) yes
C9 . C10 . H101 . 110.5 no
O1 . C10 . H101 . 108.0 no
C11 . C10 . H101 . 109.7 no
C10 . C11 . C12 . 113.38(13) yes
C10 . C11 . N16 . 113.10(11) yes
C12 . C11 . N16 . 99.69(12) yes
C10 . C11 . H111 . 108.6 no
C12 . C11 . H111 . 110.7 no
N16 . C11 . H111 . 111.2 no
C11 . C12 . O13 . 104.51(13) yes
C11 . C12 . H122 . 111.3 no
O13 . C12 . H122 . 106.4 no
C11 . C12 . H121 . 112.4 no
O13 . C12 . H121 . 108.3 no
H122 . C12 . H121 . 113.2 no
C12 . O13 . C14 . 108.79(12) yes
O13 . C14 . O15 . 121.47(14) yes
O13 . C14 . N16 . 109.63(12) yes
O15 . C14 . N16 . 128.88(15) yes
C11 . N16 . C14 . 110.80(12) yes
C11 . N16 . H161 . 122.8 no
C14 . N16 . H161 . 120.9 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
C2 . H22 . O15 2_564 137.28 0.989 2.572 3.367(2) yes
C3 . H31 . O15 2_464 135.39 0.997 2.377 3.165(2) yes
N16 . H161 . O4 2_565 145.93 0.874 2.242 3.007(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/14 at 11:22:27
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  63,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/14 at 11:22:27
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1015840'
#######################################################################
#
#                 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_25
#==============================================================================
_audit_creation_date             14-07-04
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 008jr11
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   5.8112(2)
_cell_length_b                   7.6935(2)
_cell_length_c                   23.7155(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1060.28(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,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'


_cell_formula_units_Z            4

# Given Formula = C10 H15 N1 O5 
# Dc =      1.44 Fooo =    488.00 Mu =      1.16 M =    229.23
# Found Formula = C10 H15 N1 O5 
# Dc =      1.44 FOOO =    488.00 Mu =      1.16 M =    229.23

_chemical_formula_sum            'C10 H15 N1 O5'
_chemical_formula_moiety         'C10 H15 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         229.23


_cell_measurement_reflns_used    1397
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.60

_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.116

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      150
_diffrn_reflns_number            10828
_reflns_number_total             1419
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 2390 
# Number of reflections with Friedels Law is 1419 
# Theoretical number of reflections is about 1212

_refine_special_details          
; 
 No of Reflections processed =   2389
 No of Friedel Pairs found =      971 No of Friedel Pairs used  =      971
 No of Unpaired Reflections  =     16
 No of Centric Reflections   =    431
 
 Flack parameter obtained from original refinemen
 Hooft parameter obtained with Flack x set to zero

 Friedif =       6.80     Acta A63, (2007), 257-265
 Estimated Friedel difference =     0.2534
                                                                               
 Flack & Shmueli (2007) recommend a value >200
 for general structures and >80 for enantiopure crystals

 Flack Parameter & su   -0.1103    1.3357
 Hooft Parameter & su    0.4895    0.8741
           Ton G & su    0.0209    1.7481

The absolute configuration has not been reliably determined

 For an enantiopure material, there are 2 choices, P2
 P2(correct)     0.5034   i.e. 0.503448E+00

 If 50:50 twinning is possible, there are 3 choices, P3
 P3(correct)     0.3177   i.e. 0.317710E+00                                      
 P3(rac-twin)    0.3689   i.e. 0.368933E+00                                      
 P3(inverse)     0.3134   i.e. 0.313358E+00                                      
 G               0.0209                                                          
 G S.U.          1.7481                                                          
 FLEQ            0.4895                                                           
 FLEQ S.U.       0.8741   i.e. 0.874056E+00     

 Restrained Flack x = -0.375(458)
;


_diffrn_reflns_theta_min         5.097
_diffrn_reflns_theta_max         27.453
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        27.453
_diffrn_measured_fraction_theta_full 0.982


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              0
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      0.81

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

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.32


# 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         1418
_refine_ls_number_restraints     0
_refine_ls_number_parameters     145
_oxford_refine_ls_R_factor_ref   0.0514
_refine_ls_wR_factor_ref         0.0989
_refine_ls_goodness_of_fit_ref   0.9910
_refine_ls_shift/su_max          0.0003368
_refine_ls_shift/su_mean         0.0000305


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1419
_refine_ls_R_factor_all          0.0515
_refine_ls_wR_factor_all         0.0993

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1190
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_gt          0.0883

# 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 unk


_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: 
 65.9 109. 69.2 31.1 7.84 
;

# 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
O1 O 0.6142(3) 0.7345(2) 0.56804(7) 0.0292 1.0000 Uani . . . . . .
C2 C 0.6989(5) 0.9050(3) 0.55432(12) 0.0350 1.0000 Uani . . . . . .
C3 C 0.9150(5) 0.9295(3) 0.58895(11) 0.0306 1.0000 Uani . . . . . .
O4 O 0.8635(3) 1.0024(2) 0.64301(7) 0.0334 1.0000 Uani . . . . . .
C5 C 0.9860(4) 0.9025(3) 0.68350(11) 0.0283 1.0000 Uani . . . . . .
C6 C 1.2372(5) 0.9569(4) 0.68677(12) 0.0407 1.0000 Uani . . . . . .
C7 C 0.8645(5) 0.9116(4) 0.73914(11) 0.0392 1.0000 Uani . . . . . .
O8 O 0.9705(3) 0.7284(2) 0.66222(7) 0.0284 1.0000 Uani . . . . . .
C9 C 0.9930(4) 0.7414(3) 0.60285(10) 0.0270 1.0000 Uani . . . . . .
C10 C 0.8164(4) 0.6293(3) 0.57258(10) 0.0253 1.0000 Uani . . . . . .
C11 C 0.7567(4) 0.4559(3) 0.59958(10) 0.0255 1.0000 Uani . . . . . .
C12 C 0.5869(4) 0.4656(4) 0.64887(10) 0.0299 1.0000 Uani . . . . . .
O13 O 0.3684(3) 0.4072(2) 0.62635(7) 0.0282 1.0000 Uani . . . . . .
C14 C 0.4040(4) 0.3343(3) 0.57540(10) 0.0246 1.0000 Uani . . . . . .
O15 O 0.2478(3) 0.2670(2) 0.54918(8) 0.0328 1.0000 Uani . . . . . .
N16 N 0.6257(4) 0.3473(3) 0.56098(9) 0.0266 1.0000 Uani . . . . . .
H21 H 0.5843 0.9919 0.5636 0.0420 1.0000 Uiso R . . . . .
H22 H 0.7369 0.9095 0.5139 0.0417 1.0000 Uiso R . . . . .
H31 H 1.0314 0.9965 0.5687 0.0369 1.0000 Uiso R . . . . .
H61 H 1.3128 0.8826 0.7144 0.0607 1.0000 Uiso R . . . . .
H63 H 1.2486 1.0771 0.6984 0.0612 1.0000 Uiso R . . . . .
H62 H 1.3091 0.9412 0.6501 0.0602 1.0000 Uiso R . . . . .
H71 H 0.9433 0.8399 0.7671 0.0586 1.0000 Uiso R . . . . .
H72 H 0.8592 1.0310 0.7513 0.0590 1.0000 Uiso R . . . . .
H73 H 0.7097 0.8663 0.7346 0.0584 1.0000 Uiso R . . . . .
H91 H 1.1506 0.7160 0.5906 0.0313 1.0000 Uiso R . . . . .
H101 H 0.8704 0.6073 0.5333 0.0285 1.0000 Uiso R . . . . .
H111 H 0.8966 0.3947 0.6115 0.0301 1.0000 Uiso R . . . . .
H122 H 0.6320 0.3868 0.6793 0.0358 1.0000 Uiso R . . . . .
H121 H 0.5715 0.5849 0.6630 0.0361 1.0000 Uiso R . . . . .
H161 H 0.6701 0.3247 0.5272 0.0318 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
O1 0.0223(8) 0.0238(8) 0.0414(9) 0.0032(7) -0.0053(7) -0.0011(8)
C2 0.0367(14) 0.0282(12) 0.0403(14) 0.0054(11) -0.0093(12) -0.0074(11)
C3 0.0299(13) 0.0260(12) 0.0359(13) 0.0021(10) -0.0016(11) -0.0074(11)
O4 0.0349(10) 0.0271(9) 0.0381(10) -0.0031(7) -0.0033(8) 0.0017(8)
C5 0.0241(11) 0.0278(11) 0.0330(13) -0.0038(10) -0.0038(10) -0.0032(11)
C6 0.0280(12) 0.0483(16) 0.0457(15) -0.0125(14) -0.0012(12) -0.0107(14)
C7 0.0352(13) 0.0456(15) 0.0366(13) -0.0088(12) 0.0000(12) -0.0057(15)
O8 0.0291(9) 0.0255(8) 0.0307(9) -0.0015(7) -0.0044(7) -0.0012(8)
C9 0.0204(10) 0.0277(12) 0.0330(12) -0.0013(10) -0.0003(9) -0.0047(11)
C10 0.0208(10) 0.0277(12) 0.0274(11) -0.0025(10) -0.0009(9) -0.0012(9)
C11 0.0224(10) 0.0240(11) 0.0302(11) -0.0031(9) -0.0024(9) -0.0008(11)
C12 0.0266(12) 0.0349(12) 0.0283(12) -0.0029(10) -0.0014(10) -0.0059(11)
O13 0.0243(8) 0.0310(8) 0.0292(8) -0.0050(7) 0.0019(7) -0.0049(8)
C14 0.0266(11) 0.0189(9) 0.0283(11) 0.0015(9) 0.0015(10) -0.0032(10)
O15 0.0290(8) 0.0350(9) 0.0342(8) -0.0055(8) -0.0023(7) -0.0101(9)
N16 0.0227(10) 0.0260(9) 0.0311(10) -0.0063(8) 0.0042(9) -0.0013(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.044(7)
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
O1 . C2 . 1.438(3) yes
O1 . C10 . 1.431(3) yes
C2 . C3 . 1.512(4) yes
C2 . H21 . 0.969 no
C2 . H22 . 0.985 no
C3 . O4 . 1.431(3) yes
C3 . C9 . 1.552(3) yes
C3 . H31 . 0.976 no
O4 . C5 . 1.421(3) yes
C5 . C6 . 1.521(4) yes
C5 . C7 . 1.498(4) yes
C5 . O8 . 1.434(3) yes
C6 . H61 . 0.975 no
C6 . H63 . 0.967 no
C6 . H62 . 0.973 no
C7 . H71 . 0.976 no
C7 . H72 . 0.964 no
C7 . H73 . 0.971 no
O8 . C9 . 1.418(3) yes
C9 . C10 . 1.521(3) yes
C9 . H91 . 0.980 no
C10 . C11 . 1.520(3) yes
C10 . H101 . 0.998 no
C11 . C12 . 1.531(3) yes
C11 . N16 . 1.455(3) yes
C11 . H111 . 0.981 no
C12 . O13 . 1.449(3) yes
C12 . H122 . 0.978 no
C12 . H121 . 0.981 no
O13 . C14 . 1.348(3) yes
C14 . O15 . 1.216(3) yes
C14 . N16 . 1.337(3) yes
N16 . H161 . 0.858 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
C2 . O1 . C10 . 104.57(18) yes
O1 . C2 . C3 . 106.0(2) yes
O1 . C2 . H21 . 110.1 no
C3 . C2 . H21 . 111.2 no
O1 . C2 . H22 . 109.2 no
C3 . C2 . H22 . 109.8 no
H21 . C2 . H22 . 110.5 no
C2 . C3 . O4 . 111.2(2) yes
C2 . C3 . C9 . 103.99(19) yes
O4 . C3 . C9 . 103.66(18) yes
C2 . C3 . H31 . 112.0 no
O4 . C3 . H31 . 112.2 no
C9 . C3 . H31 . 113.2 no
C3 . O4 . C5 . 106.78(18) yes
O4 . C5 . C6 . 111.5(2) yes
O4 . C5 . C7 . 109.5(2) yes
C6 . C5 . C7 . 113.2(2) yes
O4 . C5 . O8 . 103.65(18) yes
C6 . C5 . O8 . 109.6(2) yes
C7 . C5 . O8 . 108.9(2) yes
C5 . C6 . H61 . 107.8 no
C5 . C6 . H63 . 110.1 no
H61 . C6 . H63 . 109.8 no
C5 . C6 . H62 . 109.4 no
H61 . C6 . H62 . 109.6 no
H63 . C6 . H62 . 110.2 no
C5 . C7 . H71 . 110.5 no
C5 . C7 . H72 . 108.9 no
H71 . C7 . H72 . 110.5 no
C5 . C7 . H73 . 108.7 no
H71 . C7 . H73 . 107.9 no
H72 . C7 . H73 . 110.2 no
C5 . O8 . C9 . 106.12(18) yes
C3 . C9 . O8 . 104.47(19) yes
C3 . C9 . C10 . 103.36(19) yes
O8 . C9 . C10 . 111.49(19) yes
C3 . C9 . H91 . 113.3 no
O8 . C9 . H91 . 111.6 no
C10 . C9 . H91 . 112.1 no
C9 . C10 . O1 . 105.63(18) yes
C9 . C10 . C11 . 116.9(2) yes
O1 . C10 . C11 . 109.91(18) yes
C9 . C10 . H101 . 108.9 no
O1 . C10 . H101 . 106.5 no
C11 . C10 . H101 . 108.4 no
C10 . C11 . C12 . 115.2(2) yes
C10 . C11 . N16 . 111.01(19) yes
C12 . C11 . N16 . 99.86(18) yes
C10 . C11 . H111 . 110.7 no
C12 . C11 . H111 . 109.6 no
N16 . C11 . H111 . 109.9 no
C11 . C12 . O13 . 105.56(18) yes
C11 . C12 . H122 . 111.1 no
O13 . C12 . H122 . 108.3 no
C11 . C12 . H121 . 111.4 no
O13 . C12 . H121 . 109.6 no
H122 . C12 . H121 . 110.6 no
C12 . O13 . C14 . 108.94(18) yes
O13 . C14 . O15 . 121.4(2) yes
O13 . C14 . N16 . 110.3(2) yes
O15 . C14 . N16 . 128.4(2) yes
C11 . N16 . C14 . 112.7(2) yes
C11 . N16 . H161 . 123.1 no
C14 . N16 . H161 . 120.9 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
C3 . H31 . O15 1_665 152.59 0.976 2.476 3.372(4) yes
N16 . H161 . O15 3_556 170.24 0.858 1.997 2.846(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/14 at 12:31:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  63,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/14 at 12:31:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1015841'
#######################################################################
#
#                 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_26
#==============================================================================
_audit_creation_date             14-07-04
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 007jr11
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   5.7625(2)
_cell_length_b                   8.6145(3)
_cell_length_c                   21.3435(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1059.51(7)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,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'


_cell_formula_units_Z            4

# Given Formula = C10 H15 N1 O5 
# Dc =      1.44 Fooo =    488.00 Mu =      1.16 M =    229.23
# Found Formula = C10 H15 N1 O5 
# Dc =      1.44 FOOO =    488.00 Mu =      1.16 M =    229.23

_chemical_formula_sum            'C10 H15 N1 O5'
_chemical_formula_moiety         'C10 H15 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         229.23

_cell_measurement_reflns_used    1400
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.116

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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      150
_diffrn_reflns_number            6899
_reflns_number_total             1428
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections without Friedels Law is 2410 
# Number of reflections with Friedels Law is 1428 
# Theoretical number of reflections is about 1214 

_refine_special_details          
; 
 No of Reflections processed =   2410
 No of Friedel Pairs found =      982 No of Friedel Pairs used  =      982
 No of Unpaired Reflections  =     12
 No of Centric Reflections   =    434
 
 Flack parameter obtained from original refinemen
 Hooft parameter obtained with Flack x set to zero

 Friedif =       6.80     Acta A63, (2007), 257-265
 Estimated Friedel difference =     0.2534
                                                                               
 Flack & Shmueli (2007) recommend a value >200
 for general structures and >80 for enantiopure crystals

 Flack Parameter & su    1.0512    1.479
 Hooft Parameter & su    0.6797    0.9308
           Ton G & su   -0.3593    1.8616

The absolute configuration has not been reliably determined

 For an enantiopure material, there are 2 choices, P2
 P2(correct)     0.4486   i.e. 0.448623E+00

 If 50:50 twinning is possible, there are 3 choices, P3
 P3(correct)     0.2861   i.e. 0.286109E+00
 P3(rac-twin)    0.3623   i.e. 0.362250E+00
 P3(inverse)     0.3516   i.e. 0.351641E+00
 G              -0.3593
 G S.U.          1.8616
 FLEQ            0.6797
 FLEQ S.U.       0.9308   i.e. 0.930781E+00

 Restrained Flack x = 0.636(517)
;


_diffrn_reflns_theta_min         5.131
_diffrn_reflns_theta_max         27.474
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        27.474
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              0
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   2.32
_oxford_diffrn_Wilson_scale      0.98

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

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.44


# 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         1428
_refine_ls_number_restraints     0
_refine_ls_number_parameters     145
_oxford_refine_ls_R_factor_ref   0.0719
_refine_ls_wR_factor_ref         0.1851
_refine_ls_goodness_of_fit_ref   0.9596
_refine_ls_shift/su_max          0.0002511
_refine_ls_shift/su_mean         0.0000265


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1428
_refine_ls_R_factor_all          0.0719
_refine_ls_wR_factor_all         0.1851

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1262
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_gt          0.1718

# 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 unk


_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: 
 66.1 104. 55.1 15.5 
;

# 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
O1 O 1.0576(4) 0.7132(3) 0.69243(10) 0.0262 1.0000 Uani . . . . . .
C2 C 1.0385(6) 0.8104(3) 0.63670(15) 0.0254 1.0000 Uani . . . . . .
C3 C 0.8369(5) 0.7429(3) 0.59921(13) 0.0238 1.0000 Uani . . . . . .
O4 O 0.9182(4) 0.6322(2) 0.55445(10) 0.0273 1.0000 Uani . . . . . .
C5 C 0.7682(6) 0.5011(3) 0.55852(12) 0.0236 1.0000 Uani . . . . . .
C6 C 0.5427(7) 0.5257(4) 0.52304(15) 0.0330 1.0000 Uani . . . . . .
C7 C 0.8983(6) 0.3578(4) 0.53803(15) 0.0300 1.0000 Uani . . . . . .
O8 O 0.7221(4) 0.4896(2) 0.62482(8) 0.0241 1.0000 Uani . . . . . .
C9 C 0.6994(5) 0.6441(3) 0.64674(13) 0.0216 1.0000 Uani . . . . . .
C10 C 0.8268(5) 0.6645(3) 0.70901(13) 0.0215 1.0000 Uani . . . . . .
C11 C 0.7069(5) 0.7837(4) 0.75157(12) 0.0238 1.0000 Uani . . . . . .
C12 C 0.8223(6) 0.8003(4) 0.81589(14) 0.0269 1.0000 Uani . . . . . .
O13 O 0.6967(5) 0.6927(3) 0.85563(10) 0.0293 1.0000 Uani . . . . . .
C14 C 0.4871(6) 0.6640(3) 0.82958(15) 0.0261 1.0000 Uani . . . . . .
O15 O 0.3375(5) 0.5889(3) 0.85527(12) 0.0372 1.0000 Uani . . . . . .
N16 N 0.4812(5) 0.7274(3) 0.77066(11) 0.0262 1.0000 Uani . . . . . .
H21 H 1.0100 0.9190 0.6462 0.0290 1.0000 Uiso R . . . . .
H22 H 1.1801 0.8023 0.6117 0.0295 1.0000 Uiso R . . . . .
H31 H 0.7371 0.8240 0.5814 0.0284 1.0000 Uiso R . . . . .
H61 H 0.4363 0.4470 0.5347 0.0466 1.0000 Uiso R . . . . .
H63 H 0.4767 0.6246 0.5324 0.0475 1.0000 Uiso R . . . . .
H62 H 0.5698 0.5172 0.4780 0.0474 1.0000 Uiso R . . . . .
H71 H 0.8092 0.2668 0.5457 0.0456 1.0000 Uiso R . . . . .
H72 H 1.0441 0.3545 0.5591 0.0463 1.0000 Uiso R . . . . .
H73 H 0.9274 0.3640 0.4934 0.0452 1.0000 Uiso R . . . . .
H91 H 0.5379 0.6769 0.6499 0.0271 1.0000 Uiso R . . . . .
H101 H 0.8398 0.5628 0.7307 0.0254 1.0000 Uiso R . . . . .
H111 H 0.6905 0.8857 0.7298 0.0268 1.0000 Uiso R . . . . .
H122 H 0.8048 0.9059 0.8300 0.0331 1.0000 Uiso R . . . . .
H121 H 0.9859 0.7738 0.8148 0.0321 1.0000 Uiso R . . . . .
H161 H 0.3628 0.7188 0.7465 0.0306 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
O1 0.0186(10) 0.0390(10) 0.0210(9) 0.0016(9) -0.0004(8) 0.0010(9)
C2 0.0246(13) 0.0295(12) 0.0221(12) 0.0020(10) 0.0020(12) -0.0009(11)
C3 0.0286(14) 0.0244(11) 0.0183(11) 0.0001(9) 0.0033(12) 0.0031(11)
O4 0.0337(12) 0.0281(9) 0.0201(10) -0.0038(8) 0.0082(9) -0.0023(9)
C5 0.0272(14) 0.0307(13) 0.0127(11) 0.0001(9) 0.0008(10) -0.0004(12)
C6 0.0355(17) 0.0390(14) 0.0246(15) -0.0017(12) -0.0068(13) 0.0055(14)
C7 0.0361(17) 0.0325(13) 0.0213(13) -0.0031(10) -0.0001(13) 0.0045(13)
O8 0.0333(12) 0.0256(9) 0.0134(10) 0.0000(7) 0.0018(8) -0.0019(9)
C9 0.0206(12) 0.0258(12) 0.0182(11) -0.0007(10) -0.0012(11) 0.0009(11)
C10 0.0174(13) 0.0287(12) 0.0183(12) -0.0020(9) -0.0002(10) -0.0017(11)
C11 0.0213(14) 0.0288(12) 0.0212(13) -0.0010(10) -0.0016(11) 0.0000(12)
C12 0.0261(15) 0.0320(13) 0.0227(13) -0.0026(10) -0.0001(12) -0.0043(12)
O13 0.0315(12) 0.0360(11) 0.0203(10) 0.0005(8) -0.0034(10) -0.0066(10)
C14 0.0286(16) 0.0266(12) 0.0232(13) -0.0031(10) 0.0008(11) -0.0004(12)
O15 0.0390(13) 0.0388(12) 0.0337(12) -0.0014(10) 0.0087(11) -0.0116(12)
N16 0.0224(12) 0.0408(13) 0.0154(10) -0.0035(10) 0.0002(10) 0.0016(11)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.984(12)
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
O1 . C2 . 1.459(3) yes
O1 . C10 . 1.439(4) yes
C2 . C3 . 1.526(4) yes
C2 . H21 . 0.971 no
C2 . H22 . 0.978 no
C3 . O4 . 1.429(3) yes
C3 . C9 . 1.543(4) yes
C3 . H31 . 0.982 no
O4 . C5 . 1.425(4) yes
C5 . C6 . 1.519(5) yes
C5 . C7 . 1.509(4) yes
C5 . O8 . 1.443(3) yes
C6 . H61 . 0.947 no
C6 . H63 . 0.955 no
C6 . H62 . 0.977 no
C7 . H71 . 0.951 no
C7 . H72 . 0.954 no
C7 . H73 . 0.968 no
O8 . C9 . 1.418(3) yes
C9 . C10 . 1.528(4) yes
C9 . H91 . 0.974 no
C10 . C11 . 1.535(4) yes
C10 . H101 . 0.995 no
C11 . C12 . 1.532(4) yes
C11 . N16 . 1.446(4) yes
C11 . H111 . 0.999 no
C12 . O13 . 1.450(4) yes
C12 . H122 . 0.964 no
C12 . H121 . 0.970 no
O13 . C14 . 1.353(4) yes
C14 . O15 . 1.209(4) yes
C14 . N16 . 1.371(4) yes
N16 . H161 . 0.858 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
C2 . O1 . C10 . 107.3(2) yes
O1 . C2 . C3 . 105.4(2) yes
O1 . C2 . H21 . 113.4 no
C3 . C2 . H21 . 110.3 no
O1 . C2 . H22 . 109.9 no
C3 . C2 . H22 . 108.8 no
H21 . C2 . H22 . 108.9 no
C2 . C3 . O4 . 110.8(3) yes
C2 . C3 . C9 . 104.9(2) yes
O4 . C3 . C9 . 103.9(2) yes
C2 . C3 . H31 . 112.3 no
O4 . C3 . H31 . 114.0 no
C9 . C3 . H31 . 110.2 no
C3 . O4 . C5 . 106.8(2) yes
O4 . C5 . C6 . 112.2(2) yes
O4 . C5 . C7 . 109.2(3) yes
C6 . C5 . C7 . 113.2(3) yes
O4 . C5 . O8 . 103.1(2) yes
C6 . C5 . O8 . 109.9(3) yes
C7 . C5 . O8 . 108.6(2) yes
C5 . C6 . H61 . 108.9 no
C5 . C6 . H63 . 111.1 no
H61 . C6 . H63 . 109.0 no
C5 . C6 . H62 . 110.1 no
H61 . C6 . H62 . 108.0 no
H63 . C6 . H62 . 109.7 no
C5 . C7 . H71 . 110.9 no
C5 . C7 . H72 . 109.0 no
H71 . C7 . H72 . 111.7 no
C5 . C7 . H73 . 109.1 no
H71 . C7 . H73 . 107.9 no
H72 . C7 . H73 . 108.2 no
C5 . O8 . C9 . 106.03(19) yes
C3 . C9 . O8 . 104.7(2) yes
C3 . C9 . C10 . 105.2(2) yes
O8 . C9 . C10 . 110.5(2) yes
C3 . C9 . H91 . 112.1 no
O8 . C9 . H91 . 112.5 no
C10 . C9 . H91 . 111.4 no
C9 . C10 . O1 . 105.3(2) yes
C9 . C10 . C11 . 112.1(2) yes
O1 . C10 . C11 . 111.5(2) yes
C9 . C10 . H101 . 109.9 no
O1 . C10 . H101 . 107.6 no
C11 . C10 . H101 . 110.3 no
C10 . C11 . C12 . 113.4(3) yes
C10 . C11 . N16 . 110.3(2) yes
C12 . C11 . N16 . 99.7(2) yes
C10 . C11 . H111 . 110.8 no
C12 . C11 . H111 . 112.1 no
N16 . C11 . H111 . 110.0 no
C11 . C12 . O13 . 104.4(2) yes
C11 . C12 . H122 . 108.9 no
O13 . C12 . H122 . 111.6 no
C11 . C12 . H121 . 112.2 no
O13 . C12 . H121 . 110.4 no
H122 . C12 . H121 . 109.3 no
C12 . O13 . C14 . 108.8(2) yes
O13 . C14 . O15 . 123.2(3) yes
O13 . C14 . N16 . 109.0(3) yes
O15 . C14 . N16 . 127.7(3) yes
C11 . N16 . C14 . 111.7(2) yes
C11 . N16 . H161 . 125.1 no
C14 . N16 . H161 . 122.4 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
C2 . H21 . O15 4_656 134.63 0.971 2.481 3.238(4) yes
C11 . H111 . O15 4_656 161.86 0.999 2.527 3.490(4) yes
N16 . H161 . O1 1_455 174.78 0.858 2.104 2.960(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/14 at 12:25:12
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  63,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/14 at 12:25:12
#
#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
1 3 0 x .
_database_code_depnum_ccdc_archive 'CCDC 1015842'
