# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_guin25

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H31 N O3 Se'
_chemical_formula_weight         496.49
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.25170(10)
_cell_length_b                   14.3878(2)
_cell_length_c                   24.2920(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2534.53(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    14133
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      72.75

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.4700
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Platform diffractometer, equipped with a Bruker SMART 2K
Charged-Coupled Device (CCD) Area Detector using the program SMART and
normal focus sealed tube source graphite monochromated Cu-Kα radiation.
The crystal-to-detector distance was 4.908 cm, and the data collection
was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 9.0 degree
scan in 30 frames over four different parts of the reciprocal space
(120 frames total).  One complete sphere of data was collected, to
better than 0.8Å resolution.  Upon completion of the data collection,
the first 101 frames were recollected in order to improve the decay
correction analysis.
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS Smart 2K/Platform'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.5
_diffrn_standards_number         239
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            20573
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         72.86
_reflns_number_total             4916
_reflns_number_gt                4396
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.050(16)
_refine_ls_number_reflns         4916
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se -0.05966(5) 0.44217(2) 0.808563(14) 0.05707(11) Uani 1 1 d . . .
C1 C 0.1660(4) 0.28543(19) 0.82468(11) 0.0437(6) Uani 1 1 d . . .
C2 C 0.1863(4) 0.38944(17) 0.83250(10) 0.0356(5) Uani 1 1 d . . .
C3 C 0.1962(4) 0.41387(18) 0.89402(10) 0.0382(6) Uani 1 1 d . . .
H3 H 0.1026 0.3769 0.9141 0.046 Uiso 1 1 calc R . .
C4 C 0.3845(4) 0.39800(18) 0.92073(10) 0.0386(6) Uani 1 1 d . . .
H4 H 0.4724 0.4397 0.9017 0.046 Uiso 1 1 calc R . .
N5 N 0.3661(3) 0.43341(16) 0.97804(8) 0.0381(5) Uani 1 1 d . . .
C6 C 0.2812(4) 0.36762(19) 1.01643(11) 0.0433(6) Uani 1 1 d . . .
H6A H 0.3764 0.3266 1.0316 0.052 Uiso 1 1 calc R . .
H6B H 0.1917 0.3290 0.9967 0.052 Uiso 1 1 calc R . .
C7 C 0.5380(4) 0.47190(19) 0.99979(11) 0.0429(6) Uani 1 1 d . . .
H7A H 0.6392 0.4285 0.9925 0.051 Uiso 1 1 calc R . .
H7B H 0.5271 0.4794 1.0398 0.051 Uiso 1 1 calc R . .
O11 O 0.0853(4) 0.23568(14) 0.85540(10) 0.0660(6) Uani 1 1 d . . .
O12 O 0.2494(3) 0.25700(14) 0.77846(9) 0.0556(5) Uani 1 1 d . . .
C12 C 0.2187(6) 0.1595(2) 0.76485(18) 0.0817(12) Uani 1 1 d . . .
H12A H 0.2660 0.1206 0.7943 0.123 Uiso 1 1 calc R . .
H12B H 0.2820 0.1446 0.7308 0.123 Uiso 1 1 calc R . .
H12C H 0.0876 0.1484 0.7604 0.123 Uiso 1 1 calc R . .
C22 C 0.3395(4) 0.4340(2) 0.79862(11) 0.0505(7) Uani 1 1 d . . .
H22A H 0.4565 0.4053 0.8079 0.076 Uiso 1 1 calc R . .
H22B H 0.3450 0.5000 0.8066 0.076 Uiso 1 1 calc R . .
H22C H 0.3145 0.4250 0.7598 0.076 Uiso 1 1 calc R . .
O31 O 0.1507(3) 0.50947(14) 0.89857(8) 0.0532(5) Uani 1 1 d . . .
H31 H 0.1876 0.5297 0.9286 0.080 Uiso 1 1 calc R . .
C41 C 0.4629(5) 0.29978(19) 0.91624(11) 0.0499(7) Uani 1 1 d . . .
H41A H 0.5785 0.2963 0.9362 0.075 Uiso 1 1 calc R . .
H41B H 0.4840 0.2848 0.8778 0.075 Uiso 1 1 calc R . .
H41C H 0.3759 0.2558 0.9318 0.075 Uiso 1 1 calc R . .
C61 C 0.1854(4) 0.41797(17) 1.06280(10) 0.0393(6) Uani 1 1 d . . .
C62 C 0.0411(4) 0.4785(2) 1.05161(11) 0.0500(7) Uani 1 1 d . . .
H62 H 0.0050 0.4886 1.0149 0.060 Uiso 1 1 calc R . .
C63 C -0.0495(5) 0.5238(2) 1.09330(13) 0.0569(8) Uani 1 1 d . . .
H63 H -0.1471 0.5644 1.0849 0.068 Uiso 1 1 calc R . .
C64 C 0.0015(4) 0.5103(2) 1.14749(13) 0.0547(8) Uani 1 1 d . . .
H64 H -0.0596 0.5419 1.1760 0.066 Uiso 1 1 calc R . .
C65 C 0.1419(5) 0.4504(2) 1.15894(11) 0.0568(8) Uani 1 1 d . . .
H65 H 0.1761 0.4401 1.1958 0.068 Uiso 1 1 calc R . .
C66 C 0.2352(4) 0.4045(2) 1.11709(11) 0.0467(7) Uani 1 1 d . . .
H66 H 0.3327 0.3640 1.1258 0.056 Uiso 1 1 calc R . .
C71 C 0.5815(4) 0.5644(2) 0.97395(10) 0.0405(5) Uani 1 1 d . . .
C72 C 0.7208(4) 0.5737(2) 0.93505(12) 0.0504(7) Uani 1 1 d . . .
H72 H 0.7956 0.5225 0.9261 0.060 Uiso 1 1 calc R . .
C73 C 0.7493(5) 0.6588(3) 0.90932(14) 0.0622(9) Uani 1 1 d . . .
H73 H 0.8413 0.6644 0.8823 0.075 Uiso 1 1 calc R . .
C74 C 0.6451(5) 0.7342(2) 0.92294(14) 0.0651(9) Uani 1 1 d . . .
H74 H 0.6660 0.7916 0.9055 0.078 Uiso 1 1 calc R . .
C75 C 0.5084(5) 0.7261(2) 0.96246(14) 0.0608(9) Uani 1 1 d . . .
H75 H 0.4369 0.7781 0.9721 0.073 Uiso 1 1 calc R . .
C76 C 0.4773(4) 0.6415(2) 0.98763(12) 0.0498(7) Uani 1 1 d . . .
H76 H 0.3842 0.6362 1.0144 0.060 Uiso 1 1 calc R . .
C81 C -0.1114(4) 0.3639(2) 0.74588(11) 0.0455(7) Uani 1 1 d . . .
C82 C -0.0426(5) 0.3853(3) 0.69501(13) 0.0637(8) Uani 1 1 d . . .
H82 H 0.0316 0.4383 0.6902 0.076 Uiso 1 1 calc R . .
C83 C -0.0831(6) 0.3285(4) 0.65072(15) 0.0913(15) Uani 1 1 d . . .
H83 H -0.0337 0.3419 0.6158 0.110 Uiso 1 1 calc R . .
C84 C -0.1947(7) 0.2530(4) 0.6577(2) 0.0990(19) Uani 1 1 d . . .
H84 H -0.2226 0.2146 0.6275 0.119 Uiso 1 1 calc R . .
C85 C -0.2657(6) 0.2333(3) 0.7081(2) 0.0917(15) Uani 1 1 d . . .
H85 H -0.3438 0.1817 0.7124 0.110 Uiso 1 1 calc R . .
C86 C -0.2242(5) 0.2884(2) 0.75323(15) 0.0637(9) Uani 1 1 d . . .
H86 H -0.2724 0.2743 0.7882 0.076 Uiso 1 1 calc 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
Se 0.05890(19) 0.05715(18) 0.05515(17) -0.01445(16) -0.01825(17) 0.02151(16)
C1 0.0429(15) 0.0382(14) 0.0500(15) -0.0028(12) -0.0134(13) 0.0014(11)
C2 0.0372(13) 0.0305(13) 0.0391(13) 0.0004(10) -0.0028(12) 0.0042(10)
C3 0.0392(13) 0.0398(14) 0.0355(12) -0.0003(10) 0.0000(12) 0.0047(10)
C4 0.0398(14) 0.0392(14) 0.0369(13) 0.0016(10) 0.0023(12) 0.0049(11)
N5 0.0399(11) 0.0414(12) 0.0329(10) 0.0012(9) 0.0009(9) 0.0002(10)
C6 0.0516(17) 0.0376(14) 0.0408(14) 0.0021(11) 0.0017(13) -0.0022(12)
C7 0.0373(15) 0.0516(16) 0.0397(13) -0.0010(11) -0.0024(13) 0.0002(12)
O11 0.0703(16) 0.0485(12) 0.0790(15) 0.0098(11) -0.0027(14) -0.0165(12)
O12 0.0588(13) 0.0468(12) 0.0611(12) -0.0166(10) -0.0058(11) 0.0125(10)
C12 0.091(3) 0.047(2) 0.107(3) -0.032(2) -0.023(3) 0.0162(19)
C22 0.0579(17) 0.0513(16) 0.0423(14) 0.0085(13) 0.0039(13) -0.0056(14)
O31 0.0574(13) 0.0496(12) 0.0527(12) -0.0144(9) -0.0158(11) 0.0194(10)
C41 0.0557(17) 0.0488(16) 0.0452(14) -0.0020(12) -0.0067(15) 0.0166(14)
C61 0.0436(14) 0.0367(14) 0.0378(12) 0.0040(10) 0.0021(12) -0.0063(11)
C62 0.0442(16) 0.0642(18) 0.0418(13) 0.0059(12) -0.0020(14) 0.0039(14)
C63 0.0462(16) 0.0595(18) 0.0649(18) 0.0050(14) 0.0033(17) 0.0118(15)
C64 0.0542(19) 0.0569(18) 0.0530(17) -0.0077(14) 0.0103(15) -0.0011(14)
C65 0.068(2) 0.064(2) 0.0388(14) -0.0025(14) -0.0019(14) -0.0043(18)
C66 0.0487(16) 0.0489(16) 0.0425(14) 0.0048(12) -0.0047(14) 0.0031(13)
C71 0.0362(13) 0.0481(14) 0.0373(11) -0.0062(11) -0.0067(11) -0.0030(13)
C72 0.0387(14) 0.060(2) 0.0524(15) -0.0047(14) 0.0043(13) -0.0047(13)
C73 0.0511(19) 0.080(3) 0.0550(18) 0.0031(17) 0.0031(16) -0.0229(18)
C74 0.070(2) 0.055(2) 0.070(2) 0.0121(17) -0.014(2) -0.0218(17)
C75 0.070(2) 0.0469(17) 0.0651(19) -0.0057(14) -0.0105(17) 0.0021(15)
C76 0.0502(19) 0.0545(17) 0.0446(14) -0.0074(12) 0.0006(14) 0.0020(14)
C81 0.0407(16) 0.0534(16) 0.0423(14) -0.0070(12) -0.0105(13) 0.0132(12)
C82 0.0502(17) 0.090(2) 0.0512(16) 0.0076(16) -0.0050(19) 0.0122(17)
C83 0.069(3) 0.158(4) 0.0471(19) -0.017(2) -0.007(2) 0.053(3)
C84 0.085(3) 0.118(4) 0.094(3) -0.057(3) -0.047(3) 0.048(3)
C85 0.077(3) 0.072(3) 0.126(4) -0.031(3) -0.042(3) 0.007(2)
C86 0.0522(19) 0.067(2) 0.072(2) -0.0061(17) -0.0072(18) 0.0041(16)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se C81 . . 1.931(3) Y
Se C2 . . 2.024(3) Y
C1 O11 . . 1.188(3) Y
C1 O12 . . 1.339(3) Y
C1 C2 . . 1.516(3) Y
C2 C22 . . 1.524(4) Y
C2 C3 . . 1.537(3) Y
C3 O31 . . 1.419(3) Y
C3 C4 . . 1.529(4) Y
C3 H3 . . 0.99 ?
C4 N5 . . 1.488(3) Y
C4 C41 . . 1.527(4) Y
C4 H4 . . 0.99 ?
N5 C7 . . 1.462(3) Y
N5 C6 . . 1.464(3) Y
C6 C61 . . 1.509(4) Y
C6 H6a . . 0.98 ?
C6 H6b . . 0.98 ?
C7 C71 . . 1.506(4) Y
C7 H7a . . 0.98 ?
C7 H7b . . 0.98 ?
O12 C12 . . 1.459(4) Y
C12 H12a . . 0.97 ?
C12 H12b . . 0.97 ?
C12 H12c . . 0.97 ?
C22 H22a . . 0.97 ?
C22 H22b . . 0.97 ?
C22 H22c . . 0.97 ?
O31 H31 . . 0.83 ?
C41 H41a . . 0.97 ?
C41 H41b . . 0.97 ?
C41 H41c . . 0.97 ?
C61 C66 . . 1.381(4) Y
C61 C62 . . 1.388(4) Y
C62 C63 . . 1.372(4) Y
C62 H62 . . 0.94 ?
C63 C64 . . 1.381(4) Y
C63 H63 . . 0.94 ?
C64 C65 . . 1.362(4) Y
C64 H64 . . 0.94 ?
C65 C66 . . 1.389(4) Y
C65 H65 . . 0.94 ?
C66 H66 . . 0.94 ?
C71 C76 . . 1.382(4) Y
C71 C72 . . 1.390(4) Y
C72 C73 . . 1.390(5) Y
C72 H72 . . 0.94 ?
C73 C74 . . 1.363(5) Y
C73 H73 . . 0.94 ?
C74 C75 . . 1.385(5) Y
C74 H74 . . 0.94 ?
C75 C76 . . 1.381(4) Y
C75 H75 . . 0.94 ?
C76 H76 . . 0.94 ?
C81 C82 . . 1.368(4) Y
C81 C86 . . 1.371(5) Y
C82 C83 . . 1.382(5) Y
C82 H82 . . 0.94 ?
C83 C84 . . 1.365(7) Y
C83 H83 . . 0.94 ?
C84 C85 . . 1.359(7) Y
C84 H84 . . 0.94 ?
C85 C86 . . 1.386(5) Y
C85 H85 . . 0.94 ?
C86 H86 . . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C81 SE C2 . . . 100.31(11) Y
O11 C1 O12 . . . 124.4(3) Y
O11 C1 C2 . . . 124.3(3) Y
O12 C1 C2 . . . 111.3(2) Y
C1 C2 C22 . . . 114.7(2) Y
C1 C2 C3 . . . 110.6(2) Y
C22 C2 C3 . . . 113.3(2) Y
C1 C2 SE . . . 104.40(18) Y
C22 C2 SE . . . 109.26(17) Y
C3 C2 SE . . . 103.58(17) Y
O31 C3 C4 . . . 108.6(2) Y
O31 C3 C2 . . . 106.6(2) Y
C4 C3 C2 . . . 114.8(2) Y
O31 C3 H3 . . . 108.9 ?
C4 C3 H3 . . . 108.9 ?
C2 C3 H3 . . . 108.9 ?
N5 C4 C41 . . . 114.6(2) Y
N5 C4 C3 . . . 105.4(2) Y
C41 C4 C3 . . . 116.1(2) Y
N5 C4 H4 . . . 106.7 ?
C41 C4 H4 . . . 106.7 ?
C3 C4 H4 . . . 106.7 ?
C7 N5 C6 . . . 111.9(2) Y
C7 N5 C4 . . . 113.0(2) Y
C6 N5 C4 . . . 114.3(2) Y
N5 C6 C61 . . . 111.0(2) Y
N5 C6 H6A . . . 109.4 ?
C61 C6 H6A . . . 109.4 ?
N5 C6 H6B . . . 109.4 ?
C61 C6 H6B . . . 109.4 ?
H6A C6 H6B . . . 108 ?
N5 C7 C71 . . . 111.3(2) Y
N5 C7 H7A . . . 109.4 ?
C71 C7 H7A . . . 109.4 ?
N5 C7 H7B . . . 109.4 ?
C71 C7 H7B . . . 109.4 ?
H7A C7 H7B . . . 108 ?
C1 O12 C12 . . . 114.5(3) Y
O12 C12 H12A . . . 109.5 ?
O12 C12 H12B . . . 109.5 ?
H12A C12 H12B . . . 109.5 ?
O12 C12 H12C . . . 109.5 ?
H12A C12 H12C . . . 109.5 ?
H12B C12 H12C . . . 109.5 ?
C2 C22 H22A . . . 109.5 ?
C2 C22 H22B . . . 109.5 ?
H22A C22 H22B . . . 109.5 ?
C2 C22 H22C . . . 109.5 ?
H22A C22 H22C . . . 109.5 ?
H22B C22 H22C . . . 109.5 ?
C3 O31 H31 . . . 109.5 ?
C4 C41 H41A . . . 109.5 ?
C4 C41 H41B . . . 109.5 ?
H41A C41 H41B . . . 109.5 ?
C4 C41 H41C . . . 109.5 ?
H41A C41 H41C . . . 109.5 ?
H41B C41 H41C . . . 109.5 ?
C66 C61 C62 . . . 118.2(3) Y
C66 C61 C6 . . . 121.7(3) Y
C62 C61 C6 . . . 120.1(2) Y
C63 C62 C61 . . . 121.0(3) Y
C63 C62 H62 . . . 119.5 ?
C61 C62 H62 . . . 119.5 ?
C62 C63 C64 . . . 120.6(3) Y
C62 C63 H63 . . . 119.7 ?
C64 C63 H63 . . . 119.7 ?
C65 C64 C63 . . . 118.9(3) Y
C65 C64 H64 . . . 120.5 ?
C63 C64 H64 . . . 120.5 ?
C64 C65 C66 . . . 121.1(3) Y
C64 C65 H65 . . . 119.5 ?
C66 C65 H65 . . . 119.5 ?
C61 C66 C65 . . . 120.3(3) Y
C61 C66 H66 . . . 119.9 ?
C65 C66 H66 . . . 119.9 ?
C76 C71 C72 . . . 119.0(3) Y
C76 C71 C7 . . . 119.6(2) Y
C72 C71 C7 . . . 121.4(3) Y
C71 C72 C73 . . . 119.9(3) Y
C71 C72 H72 . . . 120.1 ?
C73 C72 H72 . . . 120.1 ?
C74 C73 C72 . . . 120.6(3) Y
C74 C73 H73 . . . 119.7 ?
C72 C73 H73 . . . 119.7 ?
C73 C74 C75 . . . 119.9(3) Y
C73 C74 H74 . . . 120.1 ?
C75 C74 H74 . . . 120.1 ?
C76 C75 C74 . . . 119.9(3) Y
C76 C75 H75 . . . 120.1 ?
C74 C75 H75 . . . 120.1 ?
C75 C76 C71 . . . 120.8(3) Y
C75 C76 H76 . . . 119.6 ?
C71 C76 H76 . . . 119.6 ?
C82 C81 C86 . . . 120.9(3) Y
C82 C81 SE . . . 120.7(3) Y
C86 C81 SE . . . 118.4(2) Y
C81 C82 C83 . . . 119.5(4) Y
C81 C82 H82 . . . 120.3 ?
C83 C82 H82 . . . 120.3 ?
C84 C83 C82 . . . 120.0(4) Y
C84 C83 H83 . . . 120 ?
C82 C83 H83 . . . 120 ?
C85 C84 C83 . . . 120.2(4) Y
C85 C84 H84 . . . 119.9 ?
C83 C84 H84 . . . 119.9 ?
C84 C85 C86 . . . 120.7(4) Y
C84 C85 H85 . . . 119.6 ?
C86 C85 H85 . . . 119.6 ?
C81 C86 C85 . . . 118.7(4) Y
C81 C86 H86 . . . 120.7 ?
C85 C86 H86 . . . 120.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 C1 C2 C22 . . . . 162.6(3) Y
O12 C1 C2 C22 . . . . -18.0(3) Y
O11 C1 C2 C3 . . . . 33.0(4) Y
O12 C1 C2 C3 . . . . -147.6(2) Y
O11 C1 C2 SE . . . . -77.9(3) Y
O12 C1 C2 SE . . . . 101.6(2) Y
C81 SE C2 C1 . . . . -39.2(2) Y
C81 SE C2 C22 . . . . 83.9(2) Y
C81 SE C2 C3 . . . . -155.07(17) Y
C1 C2 C3 O31 . . . . -160.2(2) Y
C22 C2 C3 O31 . . . . 69.4(3) Y
SE C2 C3 O31 . . . . -48.8(2) Y
C1 C2 C3 C4 . . . . 79.4(3) Y
C22 C2 C3 C4 . . . . -51.0(3) Y
SE C2 C3 C4 . . . . -169.20(18) Y
O31 C3 C4 N5 . . . . 56.0(3) Y
C2 C3 C4 N5 . . . . 175.3(2) Y
O31 C3 C4 C41 . . . . -175.9(2) Y
C2 C3 C4 C41 . . . . -56.6(3) Y
C41 C4 N5 C7 . . . . 82.8(3) Y
C3 C4 N5 C7 . . . . -148.2(2) Y
C41 C4 N5 C6 . . . . -46.7(3) Y
C3 C4 N5 C6 . . . . 82.3(3) Y
C7 N5 C6 C61 . . . . 77.1(3) Y
C4 N5 C6 C61 . . . . -152.7(2) Y
C6 N5 C7 C71 . . . . -156.0(2) Y
C4 N5 C7 C71 . . . . 73.2(3) Y
O11 C1 O12 C12 . . . . 5.9(4) Y
C2 C1 O12 C12 . . . . -173.5(3) Y
N5 C6 C61 C66 . . . . -120.3(3) Y
N5 C6 C61 C62 . . . . 60.8(3) Y
C66 C61 C62 C63 . . . . 0.1(4) Y
C6 C61 C62 C63 . . . . 179.0(3) Y
C61 C62 C63 C64 . . . . 0.2(5) Y
C62 C63 C64 C65 . . . . -0.8(5) Y
C63 C64 C65 C66 . . . . 1.0(5) Y
C62 C61 C66 C65 . . . . 0.2(4) Y
C6 C61 C66 C65 . . . . -178.7(3) Y
C64 C65 C66 C61 . . . . -0.8(5) Y
N5 C7 C71 C76 . . . . 71.7(3) Y
N5 C7 C71 C72 . . . . -106.1(3) Y
C76 C71 C72 C73 . . . . -2.1(4) Y
C7 C71 C72 C73 . . . . 175.7(3) Y
C71 C72 C73 C74 . . . . 1.8(5) Y
C72 C73 C74 C75 . . . . -0.5(5) Y
C73 C74 C75 C76 . . . . -0.5(5) Y
C74 C75 C76 C71 . . . . 0.1(5) Y
C72 C71 C76 C75 . . . . 1.2(4) Y
C7 C71 C76 C75 . . . . -176.7(3) Y
C2 SE C81 C82 . . . . -85.4(2) Y
C2 SE C81 C86 . . . . 97.1(2) Y
C86 C81 C82 C83 . . . . -1.9(5) Y
SE C81 C82 C83 . . . . -179.4(3) Y
C81 C82 C83 C84 . . . . 1.7(6) Y
C82 C83 C84 C85 . . . . -0.3(6) Y
C83 C84 C85 C86 . . . . -0.9(7) Y
C82 C81 C86 C85 . . . . 0.8(5) Y
SE C81 C86 C85 . . . . 178.4(3) Y
C84 C85 C86 C81 . . . . 0.6(6) Y

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O31 H31 N5 0.83 2.24 2.714(3) 116.1 .



_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        72.86
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1001298'
#######################################################################
#
#                 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_guin33

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 N O2'
_chemical_formula_weight         127.14
_chemical_compound_source        'Synthesized by the authors. See text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P212121
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.38220(10)
_cell_length_b                   7.7125(2)
_cell_length_c                   19.0393(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     643.48(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7196
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      72.59

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_Type   multi-scan
_exptl_absorpt_correction_T_min  0.9100
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'

_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Platform diffractometer, equipped with a Bruker SMART 2K
Charged-Coupled Device (CCD) Area Detector using the program SMART and
normal focus sealed tube source graphite monochromated Cu-Kα radiation.
The crystal-to-detector distance was 4.908 cm, and the data collection
was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 9.0 degree
scan in 30 frames over four different parts of the reciprocal space
(120 frames total).  One complete sphere of data was collected, to
better than 0.8Å resolution.  Upon completion of the data collection,
the first 101 frames were recollected in order to improve the decay
correction analysis.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.5
_diffrn_standards_number         66
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        -0.08
_diffrn_reflns_number            7763
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         72.57
_reflns_number_total             1244
_reflns_number_gt                1220
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.1359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs'
_chemical_absolute_configuration rmad
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_number_reflns         1244
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O10 O 0.9473(3) 0.30142(13) 0.75210(5) 0.0244(3) Uani 1 1 d . . .
C1 C 0.8293(4) 0.24676(19) 0.80653(7) 0.0173(3) Uani 1 1 d . . .
C2 C 0.6591(4) 0.35377(19) 0.86089(7) 0.0162(3) Uani 1 1 d . . .
C3 C 0.5430(3) 0.22836(19) 0.91223(7) 0.0174(3) Uani 1 1 d . . .
H3 H 0.3445 0.2496 0.9367 0.021 Uiso 1 1 calc R . .
C4 C 0.6302(4) 0.04622(18) 0.88924(7) 0.0177(3) Uani 1 1 d . . .
H4 H 0.4424 -0.0166 0.8736 0.021 Uiso 1 1 calc R . .
N5 N 0.8239(3) 0.08073(16) 0.82783(6) 0.0180(3) Uani 1 1 d . . .
H5 H 0.9286 -0.0013 0.8066 0.022 Uiso 1 1 calc R . .
O6 O 0.8087(3) 0.33303(12) 0.92903(5) 0.0182(3) Uani 1 1 d . . .
C20 C 0.5332(4) 0.52793(19) 0.84324(8) 0.0213(3) Uani 1 1 d . . .
H20A H 0.6983 0.6032 0.8266 0.032 Uiso 1 1 calc R . .
H20B H 0.4396 0.5790 0.8852 0.032 Uiso 1 1 calc R . .
H20C H 0.3789 0.5161 0.8063 0.032 Uiso 1 1 calc R . .
C40 C 0.7905(4) -0.06040(18) 0.94562(8) 0.0205(3) Uani 1 1 d . . .
H40A H 0.9677 0.0038 0.9632 0.031 Uiso 1 1 calc R . .
H40B H 0.8580 -0.1709 0.9255 0.031 Uiso 1 1 calc R . .
H40C H 0.6488 -0.0826 0.9844 0.031 Uiso 1 1 calc 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
O10 0.0351(7) 0.0206(5) 0.0174(5) -0.0006(4) 0.0077(5) -0.0048(5)
C1 0.0202(8) 0.0180(6) 0.0137(6) -0.0017(5) -0.0021(5) -0.0031(6)
C2 0.0189(7) 0.0177(7) 0.0121(6) -0.0014(5) -0.0022(5) -0.0025(6)
C3 0.0166(7) 0.0210(7) 0.0147(6) 0.0000(5) -0.0004(5) 0.0000(6)
C4 0.0190(8) 0.0186(7) 0.0154(7) -0.0001(5) 0.0009(6) -0.0032(5)
N5 0.0237(7) 0.0171(5) 0.0131(5) -0.0021(4) 0.0025(5) 0.0006(5)
O6 0.0204(6) 0.0210(5) 0.0132(5) -0.0014(4) -0.0025(4) -0.0004(4)
C20 0.0271(9) 0.0183(7) 0.0185(7) -0.0006(6) -0.0013(6) -0.0002(6)
C40 0.0248(8) 0.0186(7) 0.0180(7) 0.0016(5) -0.0010(6) -0.0009(6)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O10 C1 . . 1.2325(18) Y
C1 N5 . . 1.3434(19) Y
C1 C2 . . 1.519(2) Y
C2 O6 . . 1.4623(17) Y
C2 C3 . . 1.466(2) Y
C2 C20 . . 1.491(2) Y
C3 O6 . . 1.4525(18) Y
C3 C4 . . 1.5201(19) Y
C3 H3 . . 1 ?
C4 N5 . . 1.4692(18) Y
C4 C40 . . 1.524(2) Y
C4 H4 . . 1 ?
N5 H5 . . 0.88 ?
C20 H20a . . 0.98 ?
C20 H20b . . 0.98 ?
C20 H20c . . 0.98 ?
C40 H40a . . 0.98 ?
C40 H40b . . 0.98 ?
C40 H40c . . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O10 C1 N5 . . . 125.96(14) Y
O10 C1 C2 . . . 126.36(13) Y
N5 C1 C2 . . . 107.66(12) Y
O6 C2 C3 . . . 59.47(9) Y
O6 C2 C20 . . . 117.68(12) Y
C3 C2 C20 . . . 128.04(14) Y
O6 C2 C1 . . . 108.96(13) Y
C3 C2 C1 . . . 105.44(13) Y
C20 C2 C1 . . . 121.18(12) Y
O6 C3 C2 . . . 60.13(9) Y
O6 C3 C4 . . . 112.05(13) Y
C2 C3 C4 . . . 109.29(12) Y
O6 C3 H3 . . . 120.3 ?
C2 C3 H3 . . . 120.3 ?
C4 C3 H3 . . . 120.3 ?
N5 C4 C3 . . . 101.95(11) Y
N5 C4 C40 . . . 113.08(12) Y
C3 C4 C40 . . . 114.31(12) Y
N5 C4 H4 . . . 109.1 ?
C3 C4 H4 . . . 109.1 ?
C40 C4 H4 . . . 109.1 ?
C1 N5 C4 . . . 115.03(12) Y
C1 N5 H5 . . . 122.5 ?
C4 N5 H5 . . . 122.5 ?
C3 O6 C2 . . . 60.41(9) Y
C2 C20 H20A . . . 109.5 ?
C2 C20 H20B . . . 109.5 ?
H20A C20 H20B . . . 109.5 ?
C2 C20 H20C . . . 109.5 ?
H20A C20 H20C . . . 109.5 ?
H20B C20 H20C . . . 109.5 ?
C4 C40 H40A . . . 109.5 ?
C4 C40 H40B . . . 109.5 ?
H40A C40 H40B . . . 109.5 ?
C4 C40 H40C . . . 109.5 ?
H40A C40 H40C . . . 109.5 ?
H40B C40 H40C . . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O10 C1 C2 O6 . . . . -121.91(16) Y
N5 C1 C2 O6 . . . . 59.09(16) Y
O10 C1 C2 C3 . . . . 175.63(14) Y
N5 C1 C2 C3 . . . . -3.36(17) Y
O10 C1 C2 C20 . . . . 19.5(2) Y
N5 C1 C2 C20 . . . . -159.46(13) Y
C20 C2 C3 O6 . . . . -102.91(16) Y
C1 C2 C3 O6 . . . . 103.21(13) Y
O6 C2 C3 C4 . . . . -104.94(13) Y
C20 C2 C3 C4 . . . . 152.15(14) Y
C1 C2 C3 C4 . . . . -1.73(17) Y
O6 C3 C4 N5 . . . . -59.04(13) Y
C2 C3 C4 N5 . . . . 5.64(16) Y
O6 C3 C4 C40 . . . . 63.31(16) Y
C2 C3 C4 C40 . . . . 128.00(13) Y
O10 C1 N5 C4 . . . . -171.36(15) Y
C2 C1 N5 C4 . . . . 7.64(17) Y
C3 C4 N5 C1 . . . . -8.37(16) Y
C40 C4 N5 C1 . . . . -131.57(13) Y
C4 C3 O6 C2 . . . . 100.27(13) Y
C20 C2 O6 C3 . . . . 119.89(16) Y
C1 C2 O6 C3 . . . . -97.13(13) Y

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 O10 0.88 1.96 2.8217(16) 164.3 3_746



_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        72.57
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 1001299'
