# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zzf-14
_database_code_depnum_ccdc_archive 'CCDC 1447696'
_audit_update_record             
;
2016-10-21 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-cyano-N'-[(1E)-(4-hydroxyphenyl)methylidene]acetohydrazide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O2'
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.7366(4)
_cell_length_b                   11.1769(10)
_cell_length_c                   18.9660(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.015(2)
_cell_angle_gamma                90
_cell_volume                     996.55(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1401
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      25.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5454
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.119
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1767
_reflns_number_gt                1289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2(Bruker, 2002)'
_computing_cell_refinement       'Bruker SAINT(Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT(Bruker, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.1448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1767
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.7465(4) 0.92970(16) 1.06910(10) 0.0981(6) Uani 1 1 d . . . . .
O2 O -0.4365(3) 0.37953(12) 0.63586(6) 0.0658(4) Uani 1 1 d . . . . .
N2 N 0.4602(2) 0.56525(12) 0.89419(6) 0.0505(4) Uani 1 1 d . . . . .
O1 O 0.9805(2) 0.65629(10) 1.03099(6) 0.0606(3) Uani 1 1 d . . . . .
C1 C 0.7666(3) 0.65807(14) 0.98691(8) 0.0498(4) Uani 1 1 d . . . . .
C4 C 0.4214(3) 0.46718(15) 0.86013(8) 0.0496(4) Uani 1 1 d . . . . .
C5 C 0.1887(3) 0.44853(13) 0.80359(8) 0.0451(4) Uani 1 1 d . . . . .
N1 N 0.7017(3) 0.56568(13) 0.94359(7) 0.0545(4) Uani 1 1 d . . . . .
C8 C -0.2356(3) 0.40570(14) 0.69136(8) 0.0491(4) Uani 1 1 d . . . . .
C6 C 0.0160(3) 0.54104(15) 0.77454(9) 0.0510(4) Uani 1 1 d . . . . .
C10 C 0.1435(3) 0.33483(14) 0.77541(8) 0.0531(4) Uani 1 1 d . . . . .
C7 C -0.1939(3) 0.52014(15) 0.71875(8) 0.0531(4) Uani 1 1 d . . . . .
C2 C 0.5653(4) 0.76311(16) 0.98059(10) 0.0554(4) Uani 1 1 d . . . . .
C9 C -0.0669(4) 0.31335(15) 0.72008(9) 0.0555(4) Uani 1 1 d . . . . .
C3 C 0.6678(4) 0.85698(17) 1.03014(9) 0.0640(5) Uani 1 1 d . . . . .
H7 H -0.311(3) 0.5840(15) 0.6975(8) 0.063(5) Uiso 1 1 d . . . . .
H9 H -0.097(3) 0.2361(16) 0.7020(8) 0.065(5) Uiso 1 1 d . . . . .
H10 H 0.265(3) 0.2692(15) 0.7951(8) 0.062(5) Uiso 1 1 d . . . . .
H4 H 0.551(3) 0.4012(14) 0.8701(7) 0.052(4) Uiso 1 1 d . . . . .
H1 H 0.816(4) 0.4943(17) 0.9473(9) 0.079(6) Uiso 1 1 d . . . . .
H6 H 0.049(3) 0.6214(15) 0.7928(8) 0.061(5) Uiso 1 1 d . . . . .
H2A H 0.543(4) 0.7961(17) 0.9330(10) 0.081(6) Uiso 1 1 d . . . . .
H2B H 0.382(4) 0.7388(16) 0.9897(9) 0.082(6) Uiso 1 1 d . . . . .
H2 H -0.541(4) 0.449(2) 0.6175(11) 0.113(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
N3 C3 1.131(2) . ?
O2 C8 1.3618(17) . ?
O2 H2 0.96(2) . ?
N2 C4 1.274(2) . ?
N2 N1 1.3872(15) . ?
O1 C1 1.2324(16) . ?
C1 N1 1.3321(19) . ?
C1 C2 1.508(2) . ?
C4 C5 1.456(2) . ?
C4 H4 0.963(15) . ?
C5 C10 1.385(2) . ?
C5 C6 1.390(2) . ?
N1 H1 0.963(19) . ?
C8 C9 1.376(2) . ?
C8 C7 1.386(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.969(17) . ?
C10 C9 1.377(2) . ?
C10 H10 0.977(16) . ?
C7 H7 0.962(17) . ?
C2 C3 1.452(2) . ?
C2 H2A 0.968(19) . ?
C2 H2B 0.947(19) . ?
C9 H9 0.934(17) . ?

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
C8 O2 H2 112.9(13) . . ?
C4 N2 N1 113.66(13) . . ?
O1 C1 N1 120.98(15) . . ?
O1 C1 C2 121.73(15) . . ?
N1 C1 C2 117.28(13) . . ?
N2 C4 C5 123.09(15) . . ?
N2 C4 H4 120.7(8) . . ?
C5 C4 H4 116.2(8) . . ?
C10 C5 C6 118.27(14) . . ?
C10 C5 C4 118.90(14) . . ?
C6 C5 C4 122.78(14) . . ?
C1 N1 N2 121.91(14) . . ?
C1 N1 H1 120.8(10) . . ?
N2 N1 H1 117.2(10) . . ?
O2 C8 C9 117.51(15) . . ?
O2 C8 C7 122.84(14) . . ?
C9 C8 C7 119.65(14) . . ?
C7 C6 C5 120.79(15) . . ?
C7 C6 H6 120.0(9) . . ?
C5 C6 H6 119.2(9) . . ?
C9 C10 C5 121.17(15) . . ?
C9 C10 H10 119.8(9) . . ?
C5 C10 H10 119.0(9) . . ?
C6 C7 C8 120.00(15) . . ?
C6 C7 H7 121.4(10) . . ?
C8 C7 H7 118.6(10) . . ?
C3 C2 C1 110.67(13) . . ?
C3 C2 H2A 108.5(11) . . ?
C1 C2 H2A 111.4(11) . . ?
C3 C2 H2B 109.4(11) . . ?
C1 C2 H2B 110.3(11) . . ?
H2A C2 H2B 106.5(15) . . ?
C8 C9 C10 120.12(16) . . ?
C8 C9 H9 119.5(10) . . ?
C10 C9 H9 120.3(10) . . ?
N3 C3 C2 179.5(2) . . ?

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 H2 N3 0.96(2) 1.87(2) 2.818(2) 171.5(19) 4_475
C2 H2B O1 0.947(19) 2.332(19) 3.265(2) 168.3(15) 1_455
C2 H2A O2 0.968(19) 2.576(18) 3.257(2) 127.5(13) 2_556
N1 H1 O1 0.963(19) 1.957(19) 2.9114(18) 170.5(15) 3_767

_refine_diff_density_max         0.097
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s468b_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1klfxh
_database_code_depnum_ccdc_archive 'CCDC 1447697'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O2'
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.5944(3)
_cell_length_b                   9.3525(4)
_cell_length_c                   22.972(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.883(2)
_cell_angle_gamma                90
_cell_volume                     983.52(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2873
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      30.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14740
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         30.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2971
_reflns_number_gt                1796
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2(Bruker, 2002)'
_computing_cell_refinement       'Bruker SAINT(Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT(Bruker, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+0.1964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2971
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0786(3) 0.30860(13) 0.23096(6) 0.0462(3) Uani 1 1 d . . . . .
H1 H -0.1079 0.3994 0.2303 0.055 Uiso 1 1 calc R U . . .
N2 N 0.0965(3) 0.24660(13) 0.19208(5) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.3487(3) 0.03237(11) 0.14416(5) 0.0598(4) Uani 1 1 d . . . . .
H2 H 0.2492 0.0722 0.1673 0.090 Uiso 1 1 calc R U . . .
C1 C -0.2028(3) 0.22665(15) 0.26979(6) 0.0412(3) Uani 1 1 d . . . . .
O1 O -0.1773(3) 0.09787(12) 0.27273(5) 0.0590(4) Uani 1 1 d . . . . .
C2 C -0.3753(4) 0.31407(17) 0.31010(7) 0.0523(4) Uani 1 1 d . . . . .
H1A H -0.2533 0.3916 0.3262 0.063 Uiso 1 1 calc R U . . .
H2B H -0.5416 0.3562 0.2875 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2105(3) 0.33042(17) 0.15647(7) 0.0470(4) Uani 1 1 d . . . . .
H4 H 0.1712 0.4279 0.1578 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3992(3) 0.27706(17) 0.11427(6) 0.0439(4) Uani 1 1 d . . . . .
C7 C 0.6365(4) 0.0851(2) 0.06694(7) 0.0578(5) Uani 1 1 d . . . . .
H7 H 0.6760 -0.0119 0.0633 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4597(3) 0.13171(17) 0.10898(6) 0.0450(4) Uani 1 1 d . . . . .
C3 C -0.4773(5) 0.23416(19) 0.35681(9) 0.0717(6) Uani 1 1 d . . . . .
C10 C 0.5229(4) 0.3726(2) 0.07696(8) 0.0603(5) Uani 1 1 d . . . . .
H10 H 0.4857 0.4699 0.0801 0.072 Uiso 1 1 calc R U . . .
C8 C 0.7532(4) 0.1816(2) 0.03068(8) 0.0670(5) Uani 1 1 d . . . . .
H8 H 0.8709 0.1496 0.0024 0.080 Uiso 1 1 calc R U . . .
C9 C 0.6988(4) 0.3252(2) 0.03560(8) 0.0693(6) Uani 1 1 d . . . . .
H9 H 0.7807 0.3900 0.0110 0.083 Uiso 1 1 calc R U . . .
N3 N -0.5613(8) 0.1736(2) 0.39364(12) 0.1612(14) Uani 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
N1 C1 1.3400(18) . ?
N1 N2 1.3797(16) . ?
N1 H1 0.8600 . ?
N2 C4 1.2770(19) . ?
O2 C6 1.3588(18) . ?
O2 H2 0.8200 . ?
C1 O1 1.2114(17) . ?
C1 C2 1.510(2) . ?
C2 C3 1.419(2) . ?
C2 H1A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.443(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.392(2) . ?
C5 C6 1.395(2) . ?
C7 C8 1.369(3) . ?
C7 C6 1.384(2) . ?
C7 H7 0.9300 . ?
C3 N3 1.114(3) . ?
C10 C9 1.372(2) . ?
C10 H10 0.9300 . ?
C8 C9 1.372(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

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 N1 N2 119.70(12) . . ?
C1 N1 H1 120.1 . . ?
N2 N1 H1 120.1 . . ?
C4 N2 N1 116.76(13) . . ?
C6 O2 H2 109.5 . . ?
O1 C1 N1 124.13(13) . . ?
O1 C1 C2 123.89(14) . . ?
N1 C1 C2 111.97(13) . . ?
C3 C2 C1 113.75(14) . . ?
C3 C2 H1A 108.8 . . ?
C1 C2 H1A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H1A C2 H2B 107.7 . . ?
N2 C4 C5 121.37(14) . . ?
N2 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C10 C5 C6 118.48(15) . . ?
C10 C5 C4 119.45(15) . . ?
C6 C5 C4 122.07(14) . . ?
C8 C7 C6 120.02(17) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O2 C6 C7 118.14(15) . . ?
O2 C6 C5 121.80(13) . . ?
C7 C6 C5 120.06(15) . . ?
N3 C3 C2 178.6(2) . . ?
C9 C10 C5 120.95(18) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C7 C8 C9 120.78(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.70(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034

