# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_as42m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(4S,5R,6S,7R)-7-methyl-3-phenyl-4,5,6,7-tetrahydro-[1,2,3]triazolo
[1,5-a]pyridine-4,5,6-triol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N3 O3'
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_weight         261.28
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0280(11)
_cell_length_b                   12.5922(19)
_cell_length_c                   14.037(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1242.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7068
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.98

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11307
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1285
_reflns_number_gt                1239
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0481P)²+0.1129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1285
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_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
C1 C 0.1025(2) 0.78074(12) 0.70865(11) 0.0325(4) Uani 1 1 d . . .
C2 C -0.1077(2) 0.75761(13) 0.71144(13) 0.0366(4) Uani 1 1 d . . .
H2 H -0.1394 0.7096 0.6588 0.044 Uiso 1 1 calc R . .
C3 C -0.1677(3) 0.70526(14) 0.80581(14) 0.0446(4) Uani 1 1 d . . .
H3 H -0.2853 0.6651 0.7952 0.053 Uiso 1 1 calc R . .
C4 C -0.0159(3) 0.62982(14) 0.84285(14) 0.0447(4) Uani 1 1 d . . .
H4 H -0.0631 0.5939 0.9001 0.054 Uiso 1 1 calc R . .
C5 C 0.1664(3) 0.69085(13) 0.86719(12) 0.0397(4) Uani 1 1 d . . .
H5 H 0.1384 0.7416 0.9183 0.048 Uiso 1 1 calc R . .
C6 C 0.2203(2) 0.82991(12) 0.64364(13) 0.0341(4) Uani 1 1 d . . .
C7 C 0.1817(3) 0.87999(12) 0.55057(11) 0.0387(4) Uani 1 1 d . . .
C8 C 0.0100(3) 0.86535(15) 0.50278(13) 0.0515(5) Uani 1 1 d . . .
H8 H -0.0823 0.8208 0.5284 0.062 Uiso 1 1 calc R . .
C9 C -0.0239(4) 0.91700(17) 0.41712(14) 0.0661(6) Uani 1 1 d . . .
H9 H -0.1390 0.9070 0.3857 0.079 Uiso 1 1 calc R . .
C10 C 0.1117(5) 0.98275(16) 0.37852(15) 0.0752(8) Uani 1 1 d . . .
H10 H 0.0881 1.0177 0.3213 0.090 Uiso 1 1 calc R . .
C11 C 0.2810(5) 0.99666(18) 0.42437(15) 0.0725(8) Uani 1 1 d . . .
H11 H 0.3729 1.0409 0.3980 0.087 Uiso 1 1 calc R . .
C12 C 0.3173(3) 0.94562(15) 0.50951(13) 0.0540(5) Uani 1 1 d . . .
H12 H 0.4338 0.9553 0.5396 0.065 Uiso 1 1 calc R . .
C13 C 0.3271(3) 0.61918(17) 0.89905(14) 0.0520(5) Uani 1 1 d . . .
H13A H 0.4340 0.6617 0.9179 0.078 Uiso 1 1 calc R . .
H13B H 0.3636 0.5735 0.8474 0.078 Uiso 1 1 calc R . .
H13C H 0.2856 0.5769 0.9520 0.078 Uiso 1 1 calc R . .
N1 N 0.21827(18) 0.75062(11) 0.78006(10) 0.0342(3) Uani 1 1 d . . .
N2 N 0.3989(2) 0.77883(11) 0.76299(11) 0.0401(3) Uani 1 1 d . . .
N3 N 0.4003(2) 0.82745(12) 0.67996(11) 0.0394(3) Uani 1 1 d . . .
O1 O -0.20417(18) 0.85623(9) 0.69706(11) 0.0465(3) Uani 1 1 d . . .
O2 O -0.2002(2) 0.78144(13) 0.87797(11) 0.0632(4) Uani 1 1 d . . .
O3 O 0.0149(2) 0.55408(10) 0.77027(10) 0.0561(4) Uani 1 1 d . . .
H1O H -0.317(4) 0.8465(18) 0.6829(15) 0.055(6) Uiso 1 1 d . . .
H3O H 0.066(4) 0.5002(17) 0.7916(16) 0.071(7) Uiso 1 1 d . . .
H2O H -0.281(4) 0.824(2) 0.861(2) 0.085(9) Uiso 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.346(2) . ?
C1 C6 1.379(2) . ?
C1 C2 1.506(2) . ?
C2 O1 1.429(2) . ?
C2 C3 1.539(2) . ?
C2 H2 0.9800 . ?
C3 O2 1.414(2) . ?
C3 C4 1.520(2) . ?
C3 H3 0.9800 . ?
C4 O3 1.412(2) . ?
C4 C5 1.533(2) . ?
C4 H4 0.9800 . ?
C5 N1 1.482(2) . ?
C5 C13 1.513(2) . ?
C5 H5 0.9800 . ?
C6 N3 1.364(2) . ?
C6 C7 1.476(2) . ?
C7 C12 1.387(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 N2 1.3397(19) . ?
N2 N3 1.317(2) . ?
O1 H1O 0.83(2) . ?
O2 H2O 0.82(3) . ?
O3 H3O 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 104.86(14) . . ?
N1 C1 C2 121.28(15) . . ?
C6 C1 C2 133.86(16) . . ?
O1 C2 C1 107.07(13) . . ?
O1 C2 C3 111.35(15) . . ?
C1 C2 C3 111.95(15) . . ?
O1 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
O2 C3 C4 107.01(16) . . ?
O2 C3 C2 111.74(14) . . ?
C4 C3 C2 111.72(15) . . ?
O2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
O3 C4 C3 106.43(15) . . ?
O3 C4 C5 111.80(15) . . ?
C3 C4 C5 110.46(14) . . ?
O3 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
N1 C5 C13 111.31(15) . . ?
N1 C5 C4 106.04(13) . . ?
C13 C5 C4 113.00(15) . . ?
N1 C5 H5 108.8 . . ?
C13 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
N3 C6 C1 107.41(15) . . ?
N3 C6 C7 120.75(15) . . ?
C1 C6 C7 131.84(16) . . ?
C12 C7 C8 118.29(17) . . ?
C12 C7 C6 119.74(17) . . ?
C8 C7 C6 121.95(16) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 N1 C1 111.41(13) . . ?
N2 N1 C5 121.02(13) . . ?
C1 N1 C5 127.55(14) . . ?
N3 N2 N1 106.78(13) . . ?
N2 N3 C6 109.54(13) . . ?
C2 O1 H1O 111.1(16) . . ?
C3 O2 H2O 111(2) . . ?
C4 O3 H3O 111.1(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 126.37(15) . . . . ?
C6 C1 C2 O1 -54.3(3) . . . . ?
N1 C1 C2 C3 4.1(2) . . . . ?
C6 C1 C2 C3 -176.60(16) . . . . ?
O1 C2 C3 O2 -36.0(2) . . . . ?
C1 C2 C3 O2 83.85(19) . . . . ?
O1 C2 C3 C4 -155.84(14) . . . . ?
C1 C2 C3 C4 -36.0(2) . . . . ?
O2 C3 C4 O3 179.86(14) . . . . ?
C2 C3 C4 O3 -57.52(18) . . . . ?
O2 C3 C4 C5 -58.59(19) . . . . ?
C2 C3 C4 C5 64.0(2) . . . . ?
O3 C4 C5 N1 63.89(16) . . . . ?
C3 C4 C5 N1 -54.43(19) . . . . ?
O3 C4 C5 C13 -58.3(2) . . . . ?
C3 C4 C5 C13 -176.62(15) . . . . ?
N1 C1 C6 N3 -0.52(18) . . . . ?
C2 C1 C6 N3 -179.92(18) . . . . ?
N1 C1 C6 C7 179.94(15) . . . . ?
C2 C1 C6 C7 0.5(3) . . . . ?
N3 C6 C7 C12 -14.7(2) . . . . ?
C1 C6 C7 C12 164.81(18) . . . . ?
N3 C6 C7 C8 166.73(16) . . . . ?
C1 C6 C7 C8 -13.8(3) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 177.55(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C6 C7 C12 C11 -177.37(17) . . . . ?
C6 C1 N1 N2 0.36(18) . . . . ?
C2 C1 N1 N2 179.86(15) . . . . ?
C6 C1 N1 C5 -177.73(14) . . . . ?
C2 C1 N1 C5 1.8(2) . . . . ?
C13 C5 N1 N2 -31.1(2) . . . . ?
C4 C5 N1 N2 -154.40(15) . . . . ?
C13 C5 N1 C1 146.80(17) . . . . ?
C4 C5 N1 C1 23.5(2) . . . . ?
C1 N1 N2 N3 -0.05(18) . . . . ?
C5 N1 N2 N3 178.18(13) . . . . ?
N1 N2 N3 C6 -0.29(18) . . . . ?
C1 C6 N3 N2 0.51(18) . . . . ?
C7 C6 N3 N2 -179.89(13) . . . . ?

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
O2 H2O N2 0.82(3) 2.70(3) 3.247(2) 126(2) 1_455
O3 H3O O1 0.82(2) 2.06(2) 2.8612(18) 163(2) 3_546
O1 H1O N3 0.83(2) 2.00(3) 2.814(2) 167(2) 1_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 944748'
#######################################################################
#
#                 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_as43m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(4S,5R,6S,7R)-7-methyl-3-p-tolyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]
pyridine-4,5,6-triol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3'
_chemical_formula_sum            'C14 H17 N3 O3'
_chemical_formula_weight         275.31
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5550(5)
_cell_length_b                   11.9870(8)
_cell_length_c                   15.0918(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1366.74(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7473
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13098
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1402
_reflns_number_gt                1355
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0419P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1402
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_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
C1 C 0.7569(2) 0.54530(15) 0.36552(11) 0.0359(4) Uani 1 1 d . . .
C2 C 0.9264(2) 0.49935(15) 0.32752(11) 0.0376(4) Uani 1 1 d . . .
H2 H 0.9104 0.4911 0.2634 0.045 Uiso 1 1 calc R . .
C3 C 1.0795(2) 0.58018(17) 0.34288(12) 0.0418(4) Uani 1 1 d . . .
H3 H 1.1810 0.5575 0.3067 0.050 Uiso 1 1 calc R . .
C4 C 1.0244(3) 0.69796(16) 0.31754(12) 0.0438(4) Uani 1 1 d . . .
H4 H 1.1277 0.7471 0.3215 0.053 Uiso 1 1 calc R . .
C5 C 0.8794(2) 0.74206(15) 0.37908(13) 0.0421(4) Uani 1 1 d . . .
H5 H 0.9306 0.7507 0.4384 0.051 Uiso 1 1 calc R . .
C6 C 0.5945(2) 0.49996(15) 0.38823(11) 0.0386(4) Uani 1 1 d . . .
C7 C 0.5293(2) 0.38389(15) 0.38640(12) 0.0395(4) Uani 1 1 d . . .
C8 C 0.4136(2) 0.34710(17) 0.45212(13) 0.0451(4) Uani 1 1 d . . .
H8 H 0.3763 0.3964 0.4959 0.054 Uiso 1 1 calc R . .
C9 C 0.3537(3) 0.23804(18) 0.45290(14) 0.0493(5) Uani 1 1 d . . .
H9 H 0.2759 0.2153 0.4971 0.059 Uiso 1 1 calc R . .
C10 C 0.4073(3) 0.16179(17) 0.38907(13) 0.0480(5) Uani 1 1 d . . .
C11 C 0.5212(3) 0.19945(18) 0.32378(14) 0.0533(5) Uani 1 1 d . . .
H11 H 0.5587 0.1501 0.2801 0.064 Uiso 1 1 calc R . .
C12 C 0.5807(3) 0.30854(18) 0.32191(13) 0.0487(5) Uani 1 1 d . . .
H12 H 0.6561 0.3315 0.2768 0.058 Uiso 1 1 calc R . .
C13 C 0.8032(3) 0.85326(17) 0.35160(16) 0.0575(5) Uani 1 1 d . . .
H13A H 0.7073 0.8726 0.3904 0.086 Uiso 1 1 calc R . .
H13B H 0.7604 0.8484 0.2918 0.086 Uiso 1 1 calc R . .
H13C H 0.8935 0.9095 0.3551 0.086 Uiso 1 1 calc R . .
C14 C 0.3426(3) 0.04253(19) 0.39103(17) 0.0650(6) Uani 1 1 d . . .
H14A H 0.2157 0.0417 0.3947 0.097 Uiso 1 1 calc R . .
H14B H 0.3914 0.0051 0.4417 0.097 Uiso 1 1 calc R . .
H14C H 0.3795 0.0050 0.3380 0.097 Uiso 1 1 calc R . .
N1 N 0.73970(18) 0.65535(13) 0.38404(10) 0.0393(3) Uani 1 1 d . . .
N2 N 0.5795(2) 0.67904(14) 0.41716(11) 0.0468(4) Uani 1 1 d . . .
N3 N 0.4920(2) 0.58437(14) 0.41978(11) 0.0459(4) Uani 1 1 d . . .
O1 O 0.96812(18) 0.39272(11) 0.36294(10) 0.0457(3) Uani 1 1 d . . .
H1O H 1.023(4) 0.407(2) 0.4092(17) 0.073(9) Uiso 1 1 d . . .
O2 O 1.12550(18) 0.57327(14) 0.43369(9) 0.0477(4) Uani 1 1 d . . .
H2O H 1.228(4) 0.579(2) 0.4374(17) 0.070(8) Uiso 1 1 d . . .
O3 O 0.9697(2) 0.69132(13) 0.22790(9) 0.0546(4) Uani 1 1 d . . .
H3O H 0.975(4) 0.751(2) 0.2033(16) 0.064(8) Uiso 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.355(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.507(2) . ?
C2 O1 1.421(2) . ?
C2 C3 1.526(2) . ?
C2 H2 0.9800 . ?
C3 O2 1.416(2) . ?
C3 C4 1.521(3) . ?
C3 H3 0.9800 . ?
C4 O3 1.417(2) . ?
C4 C5 1.530(3) . ?
C4 H4 0.9800 . ?
C5 N1 1.483(2) . ?
C5 C13 1.510(3) . ?
C5 H5 0.9800 . ?
C6 N3 1.360(2) . ?
C6 C7 1.476(3) . ?
C7 C12 1.383(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(3) . ?
C10 C14 1.511(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.340(2) . ?
N2 N3 1.314(2) . ?
O1 H1O 0.83(3) . ?
O2 H2O 0.78(3) . ?
O3 H3O 0.80(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 104.23(15) . . ?
N1 C1 C2 121.06(16) . . ?
C6 C1 C2 134.70(17) . . ?
O1 C2 C1 111.95(15) . . ?
O1 C2 C3 110.24(15) . . ?
C1 C2 C3 110.73(14) . . ?
O1 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
O2 C3 C4 111.39(16) . . ?
O2 C3 C2 107.20(15) . . ?
C4 C3 C2 110.09(15) . . ?
O2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
O3 C4 C3 105.53(16) . . ?
O3 C4 C5 112.95(17) . . ?
C3 C4 C5 111.35(15) . . ?
O3 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
N1 C5 C13 111.16(15) . . ?
N1 C5 C4 107.34(14) . . ?
C13 C5 C4 114.28(17) . . ?
N1 C5 H5 108.0 . . ?
C13 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
N3 C6 C1 107.40(16) . . ?
N3 C6 C7 121.17(16) . . ?
C1 C6 C7 131.36(17) . . ?
C12 C7 C8 118.04(18) . . ?
C12 C7 C6 122.34(17) . . ?
C8 C7 C6 119.62(17) . . ?
C9 C8 C7 120.68(19) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.39(18) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 117.43(19) . . ?
C11 C10 C14 121.6(2) . . ?
C9 C10 C14 120.99(19) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C7 C12 C11 120.79(19) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 N1 C1 111.72(15) . . ?
N2 N1 C5 120.88(15) . . ?
C1 N1 C5 127.12(14) . . ?
N3 N2 N1 106.41(15) . . ?
N2 N3 C6 110.22(14) . . ?
C2 O1 H1O 104.2(19) . . ?
C3 O2 H2O 108.0(19) . . ?
C4 O3 H3O 112.1(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 142.08(16) . . . . ?
C6 C1 C2 O1 -39.0(3) . . . . ?
N1 C1 C2 C3 18.6(2) . . . . ?
C6 C1 C2 C3 -162.41(18) . . . . ?
O1 C2 C3 O2 -50.23(19) . . . . ?
C1 C2 C3 O2 74.21(19) . . . . ?
O1 C2 C3 C4 -171.55(14) . . . . ?
C1 C2 C3 C4 -47.1(2) . . . . ?
O2 C3 C4 O3 -175.70(15) . . . . ?
C2 C3 C4 O3 -56.92(19) . . . . ?
O2 C3 C4 C5 -52.8(2) . . . . ?
C2 C3 C4 C5 65.98(19) . . . . ?
O3 C4 C5 N1 69.0(2) . . . . ?
C3 C4 C5 N1 -49.6(2) . . . . ?
O3 C4 C5 C13 -54.8(2) . . . . ?
C3 C4 C5 C13 -173.30(16) . . . . ?
N1 C1 C6 N3 -0.84(19) . . . . ?
C2 C1 C6 N3 -179.93(18) . . . . ?
N1 C1 C6 C7 -177.99(18) . . . . ?
C2 C1 C6 C7 2.9(3) . . . . ?
N3 C6 C7 C12 148.27(19) . . . . ?
C1 C6 C7 C12 -34.9(3) . . . . ?
N3 C6 C7 C8 -32.6(3) . . . . ?
C1 C6 C7 C8 144.21(19) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C6 C7 C8 C9 -178.60(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 C14 179.37(19) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C14 C10 C11 C12 -180.0(2) . . . . ?
C8 C7 C12 C11 -1.1(3) . . . . ?
C6 C7 C12 C11 177.99(18) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C6 C1 N1 N2 0.7(2) . . . . ?
C2 C1 N1 N2 179.96(15) . . . . ?
C6 C1 N1 C5 174.63(16) . . . . ?
C2 C1 N1 C5 -6.1(3) . . . . ?
C13 C5 N1 N2 -39.9(2) . . . . ?
C4 C5 N1 N2 -165.50(15) . . . . ?
C13 C5 N1 C1 146.72(18) . . . . ?
C4 C5 N1 C1 21.1(2) . . . . ?
C1 N1 N2 N3 -0.3(2) . . . . ?
C5 N1 N2 N3 -174.65(15) . . . . ?
N1 N2 N3 C6 -0.3(2) . . . . ?
C1 C6 N3 N2 0.7(2) . . . . ?
C7 C6 N3 N2 178.21(16) . . . . ?

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
O1 H1O O2 0.83(3) 2.17(3) 2.690(2) 120(2) .
O2 H2O N3 0.78(3) 2.02(3) 2.780(2) 168(3) 1_655
O3 H3O O1 0.80(3) 2.02(3) 2.816(2) 170(3) 3_755

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 944749'
