Electronic Supplementary Material for CrystEngComm
This Journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Prof C. Wilson'
_publ_contact_author_address     
;
Department of Chemistry
University of Glasgow
Glasgow
G12 8QQ
UNITED KINGDOM
;

_publ_contact_author_email       CHICK@CHEM.GLA.AC.UK

_publ_section_title              
;
Towards Proton Transfer in Hydrogen Bonded Molecular
Complexes: Joint Experimental and Theoretical Modelling and an Energy
Scale for Polymorphism
;
loop_
_publ_author_name
C.Wilson
'Matthias J. Gutmann'
'Derek Middlemiss'
'Marc Schmidtmann'
# Attachment 'IN-OA_Form_I.cif'

data_hain
_database_code_depnum_ccdc_archive 'CCDC 643946'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.6911(12)
_cell_length_b                   9.9945(10)
_cell_length_c                   12.1366(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.743(5)
_cell_angle_gamma                90.00
_cell_volume                     1383.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6224
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      33.95

_exptl_crystal_description       block/plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10080
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         33.97
_reflns_number_total             2782
_reflns_number_gt                2541
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0700P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2782
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
O1 O 0.03766(6) 0.69269(5) 0.65610(5) 0.01817(13) Uani 1 1 d . . .
H1 H 0.0702(12) 0.6965(14) 0.5696(11) 0.027 Uiso 1 1 d . . .
O2 O 0.03862(5) 0.91687(5) 0.65053(4) 0.01576(12) Uani 1 1 d . . .
O3 O 0.24221(5) 0.63579(5) 0.11434(4) 0.01821(13) Uani 1 1 d . . .
N1 N 0.09980(5) 0.70119(6) 0.46765(5) 0.01273(12) Uani 1 1 d . . .
N2 N 0.17231(6) 0.84781(6) 0.09236(5) 0.01396(12) Uani 1 1 d . . .
C1 C 0.02189(6) 0.81062(7) 0.69427(5) 0.01222(13) Uani 1 1 d . . .
C2 C 0.11357(6) 0.59118(6) 0.40853(6) 0.01368(13) Uani 1 1 d . . .
H2 H 0.1024(11) 0.5062(13) 0.4403(10) 0.023(3) Uiso 1 1 d . . .
C3 C 0.14390(6) 0.59928(6) 0.30467(5) 0.01307(13) Uani 1 1 d . . .
H3 H 0.1510(11) 0.5163(15) 0.2610(11) 0.032(3) Uiso 1 1 d . . .
C4 C 0.16081(6) 0.72500(6) 0.26121(5) 0.01088(12) Uani 1 1 d . . .
C5 C 0.14666(6) 0.83853(7) 0.32325(6) 0.01256(13) Uani 1 1 d . . .
H4 H 0.1587(11) 0.9315(13) 0.3004(10) 0.025(3) Uiso 1 1 d . . .
C6 C 0.11572(6) 0.82208(7) 0.42605(6) 0.01288(13) Uani 1 1 d . . .
H5 H 0.1011(11) 0.8963(12) 0.4733(10) 0.020(3) Uiso 1 1 d . . .
C7 C 0.19487(6) 0.73316(6) 0.14917(5) 0.01180(13) Uani 1 1 d . . .
H6 H 0.1919(11) 0.8533(12) 0.0229(11) 0.023(3) Uiso 1 1 d . . .
H7 H 0.1327(13) 0.9144(14) 0.1164(11) 0.029(3) Uiso 1 1 d . . .

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 0.0331(3) 0.0098(2) 0.0157(2) -0.00055(16) 0.0143(2) 0.00090(18)
O2 0.0240(3) 0.0107(2) 0.0145(2) 0.00114(15) 0.00851(19) -0.00189(16)
O3 0.0297(3) 0.0134(2) 0.0152(2) 0.00183(17) 0.0128(2) 0.00716(19)
N1 0.0162(3) 0.0122(2) 0.0110(2) 0.00053(18) 0.00560(19) 0.00134(18)
N2 0.0208(3) 0.0110(2) 0.0121(2) 0.00177(18) 0.0079(2) 0.00280(19)
C1 0.0161(3) 0.0104(3) 0.0111(3) 0.00031(18) 0.0050(2) -0.00015(19)
C2 0.0195(3) 0.0107(3) 0.0125(3) 0.00106(19) 0.0073(2) 0.0007(2)
C3 0.0189(3) 0.0100(3) 0.0118(3) -0.00011(19) 0.0066(2) 0.0011(2)
C4 0.0136(3) 0.0107(2) 0.0093(2) -0.00002(18) 0.00455(19) 0.00085(19)
C5 0.0174(3) 0.0103(2) 0.0113(2) -0.00018(19) 0.0060(2) 0.0000(2)
C6 0.0176(3) 0.0114(3) 0.0108(3) -0.00086(19) 0.0056(2) 0.0007(2)
C7 0.0153(3) 0.0108(3) 0.0104(2) 0.00005(19) 0.0052(2) 0.0010(2)

_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
O1 C1 1.2944(8) . ?
O1 H1 1.194(13) . ?
O2 C1 1.2221(8) . ?
O3 C7 1.2390(8) . ?
N1 C6 1.3382(8) . ?
N1 C2 1.3418(8) . ?
N1 H1 1.357(13) . ?
N2 C7 1.3333(8) . ?
N2 H6 0.922(13) . ?
N2 H7 0.895(14) . ?
C1 C1 1.5482(13) 2_556 ?
C2 C3 1.3851(9) . ?
C2 H2 0.953(13) . ?
C3 C4 1.3936(9) . ?
C3 H3 0.998(14) . ?
C4 C5 1.3916(9) . ?
C4 C7 1.5011(9) . ?
C5 C6 1.3834(9) . ?
C5 H4 0.989(13) . ?
C6 H5 0.976(12) . ?

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
C1 O1 H1 112.6(7) . . ?
C6 N1 C2 119.67(6) . . ?
C6 N1 H1 117.4(6) . . ?
C2 N1 H1 122.9(6) . . ?
C7 N2 H6 117.6(8) . . ?
C7 N2 H7 121.9(9) . . ?
H6 N2 H7 120.2(12) . . ?
O2 C1 O1 125.92(6) . . ?
O2 C1 C1 119.67(4) . 2_556 ?
O1 C1 C1 114.42(4) . 2_556 ?
N1 C2 C3 121.58(6) . . ?
N1 C2 H2 118.0(7) . . ?
C3 C2 H2 120.4(7) . . ?
C2 C3 C4 118.90(6) . . ?
C2 C3 H3 120.2(8) . . ?
C4 C3 H3 120.9(8) . . ?
C5 C4 C3 119.12(6) . . ?
C5 C4 C7 122.19(6) . . ?
C3 C4 C7 118.68(5) . . ?
C6 C5 C4 118.48(6) . . ?
C6 C5 H4 116.5(7) . . ?
C4 C5 H4 125.0(7) . . ?
N1 C6 C5 122.24(6) . . ?
N1 C6 H5 114.1(7) . . ?
C5 C6 H5 123.7(7) . . ?
O3 C7 N2 123.43(6) . . ?
O3 C7 C4 119.61(6) . . ?
N2 C7 C4 116.96(5) . . ?

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 H1 N1 1.194(13) 1.357(13) 2.5493(8) 176.3(12) .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        33.97
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.063

# Attachment 'IN-OA_Form_II.cif'

data_oxaiso6
_database_code_depnum_ccdc_archive 'CCDC 643947'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29

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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.6811(7)
_cell_length_b                   7.5912(14)
_cell_length_c                   12.455(2)
_cell_angle_alpha                85.638(9)
_cell_angle_beta                 87.856(10)
_cell_angle_gamma                84.221(10)
_cell_volume                     345.11(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      33.81

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             174
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8148
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         33.92
_reflns_number_total             2759
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2759
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O1 O 1.29804(19) 1.80006(8) 0.52094(5) 0.01610(15) Uani 1 1 d . . .
H1 H 1.209(4) 1.7154(19) 0.6011(11) 0.024 Uiso 1 1 d . . .
O2 O 1.50442(19) 1.96801(8) 0.64052(5) 0.01596(14) Uani 1 1 d . . .
O3 O 0.6933(2) 1.22319(9) 0.99567(5) 0.01671(15) Uani 1 1 d . . .
N1 N 1.09828(19) 1.59195(9) 0.67528(6) 0.01248(14) Uani 1 1 d . . .
N2 N 0.5882(2) 1.05275(9) 0.86038(6) 0.01344(15) Uani 1 1 d . . .
C1 C 1.4465(2) 1.93596(10) 0.54826(6) 0.01136(15) Uani 1 1 d . . .
C2 C 1.0714(2) 1.42874(11) 0.64463(6) 0.01247(15) Uani 1 1 d . . .
H2 H 1.162(4) 1.4025(18) 0.5720(10) 0.016(3) Uiso 1 1 d . . .
C3 C 0.9358(2) 1.29713(10) 0.71308(6) 0.01177(15) Uani 1 1 d . . .
H3 H 0.924(4) 1.1804(19) 0.6844(11) 0.022(3) Uiso 1 1 d . . .
C4 C 0.8316(2) 1.33598(10) 0.81781(6) 0.01015(14) Uani 1 1 d . . .
C5 C 0.8648(2) 1.50563(10) 0.84967(6) 0.01218(15) Uani 1 1 d . . .
H4 H 0.787(4) 1.5434(18) 0.9202(10) 0.019(3) Uiso 1 1 d . . .
C6 C 0.9973(2) 1.63129(10) 0.77588(7) 0.01310(16) Uani 1 1 d . . .
H5 H 1.018(4) 1.7513(19) 0.7940(11) 0.025(3) Uiso 1 1 d . . .
C7 C 0.6964(2) 1.19813(10) 0.89893(6) 0.01108(15) Uani 1 1 d . . .
H6 H 0.497(4) 0.961(2) 0.9101(12) 0.030(4) Uiso 1 1 d . . .
H7 H 0.573(4) 1.0370(18) 0.7877(11) 0.021(3) Uiso 1 1 d . . .

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 0.0257(3) 0.0132(3) 0.0111(3) -0.0010(2) 0.0007(2) -0.0107(2)
O2 0.0247(3) 0.0156(3) 0.0086(3) -0.0011(2) -0.0010(2) -0.0067(2)
O3 0.0261(3) 0.0161(3) 0.0089(3) -0.0008(2) 0.0012(2) -0.0074(2)
N1 0.0144(3) 0.0113(3) 0.0120(3) 0.0005(2) -0.0006(2) -0.0034(2)
N2 0.0201(3) 0.0116(3) 0.0093(3) 0.0000(2) -0.0005(2) -0.0055(2)
C1 0.0136(3) 0.0106(3) 0.0101(3) -0.0008(2) 0.0007(2) -0.0027(2)
C2 0.0152(3) 0.0125(3) 0.0101(3) -0.0002(2) 0.0004(3) -0.0036(3)
C3 0.0151(3) 0.0104(3) 0.0100(3) -0.0008(2) 0.0005(3) -0.0026(2)
C4 0.0113(3) 0.0099(3) 0.0092(3) 0.0002(2) -0.0004(2) -0.0015(2)
C5 0.0152(3) 0.0110(3) 0.0105(3) -0.0014(2) 0.0004(3) -0.0022(3)
C6 0.0167(3) 0.0100(3) 0.0129(3) -0.0011(2) -0.0004(3) -0.0026(3)
C7 0.0130(3) 0.0103(3) 0.0100(3) 0.0001(2) 0.0001(2) -0.0018(2)

_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
O1 C1 1.2883(10) . ?
O1 H1 1.199(14) . ?
O2 C1 1.2232(10) . ?
O3 C7 1.2334(10) . ?
N1 C2 1.3379(11) . ?
N1 C6 1.3405(11) . ?
N1 H1 1.347(14) . ?
N2 C7 1.3381(11) . ?
N2 H6 0.975(16) . ?
N2 H7 0.926(14) . ?
C1 C1 1.5523(15) 2_896 ?
C2 C3 1.3831(11) . ?
C2 H2 0.981(13) . ?
C3 C4 1.3907(11) . ?
C3 H3 0.985(14) . ?
C4 C5 1.3943(11) . ?
C4 C7 1.5066(11) . ?
C5 C6 1.3855(11) . ?
C5 H4 0.969(13) . ?
C6 H5 0.966(15) . ?

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
C1 O1 H1 108.7(7) . . ?
C2 N1 C6 119.91(7) . . ?
C2 N1 H1 118.2(6) . . ?
C6 N1 H1 121.8(6) . . ?
C7 N2 H6 119.6(9) . . ?
C7 N2 H7 124.1(9) . . ?
H6 N2 H7 116.0(13) . . ?
O2 C1 O1 125.57(7) . . ?
O2 C1 C1 120.39(9) . 2_896 ?
O1 C1 C1 114.04(8) . 2_896 ?
N1 C2 C3 122.22(7) . . ?
N1 C2 H2 117.6(8) . . ?
C3 C2 H2 120.1(8) . . ?
C2 C3 C4 118.44(7) . . ?
C2 C3 H3 117.3(8) . . ?
C4 C3 H3 124.2(8) . . ?
C3 C4 C5 119.05(7) . . ?
C3 C4 C7 121.86(7) . . ?
C5 C4 C7 119.06(7) . . ?
C6 C5 C4 119.12(7) . . ?
C6 C5 H4 117.4(8) . . ?
C4 C5 H4 123.4(8) . . ?
N1 C6 C5 121.25(7) . . ?
N1 C6 H5 117.0(8) . . ?
C5 C6 H5 121.7(8) . . ?
O3 C7 N2 123.71(7) . . ?
O3 C7 C4 119.38(7) . . ?
N2 C7 C4 116.91(7) . . ?

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 H1 N1 1.199(14) 1.347(14) 2.5294(10) 166.8(13) .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        33.92
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.077

