# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1479795'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N2 O'
_chemical_formula_sum            'C9 H8 N2 O'
_chemical_formula_weight         160.17

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           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                   5.7785(12)
_cell_length_b                   9.7172(19)
_cell_length_c                   14.760(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     828.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      3.465
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7986
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1904
_reflns_number_gt                1467
_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 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)+(0.0568P)²+0.0094P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.7(17)
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C8 C -0.0865(3) 0.09232(16) 0.37826(10) 0.0582(4) Uani 1 1 d . . .
C7 C 0.0859(2) 0.18897(14) 0.35882(8) 0.0463(3) Uani 1 1 d . . .
C6 C 0.1084(2) 0.33358(14) 0.38708(8) 0.0473(3) Uani 1 1 d . . .
C5 C 0.2998(3) 0.41320(16) 0.36041(10) 0.0564(4) Uani 1 1 d . . .
O1 O 0.47358(18) 0.35920(12) 0.30876(8) 0.0743(4) Uani 1 1 d . . .
H5 H 0.4458 0.2781 0.2980 0.112 Uiso 1 1 calc R . .
N1 N 0.2483(2) 0.13202(13) 0.30647(9) 0.0599(3) Uani 1 1 d . . .
C1 C -0.0621(3) 0.39580(16) 0.44012(10) 0.0589(4) Uani 1 1 d . . .
N2 N 0.1791(2) 0.00171(13) 0.29347(10) 0.0660(4) Uani 1 1 d . . .
C4 C 0.3148(4) 0.5500(2) 0.38573(14) 0.0765(5) Uani 1 1 d . . .
C2 C -0.0459(4) 0.53130(19) 0.46544(13) 0.0738(5) Uani 1 1 d . . .
C9 C -0.0199(3) -0.02468(17) 0.33506(11) 0.0633(4) Uani 1 1 d . . .
C3 C 0.1412(4) 0.60792(19) 0.43722(14) 0.0831(6) Uani 1 1 d . . .
H7 H -0.095(3) -0.1115(17) 0.3276(11) 0.067(4) Uiso 1 1 d . . .
H6 H 0.266(4) -0.0477(19) 0.2545(14) 0.087(6) Uiso 1 1 d . . .
H8 H -0.226(3) 0.1050(18) 0.4138(11) 0.065(4) Uiso 1 1 d . . .
H4 H 0.454(4) 0.5989(18) 0.3597(13) 0.087(6) Uiso 1 1 d . . .
H1 H -0.204(3) 0.3412(17) 0.4601(12) 0.070(5) Uiso 1 1 d . . .
H3 H 0.148(4) 0.702(3) 0.4561(14) 0.109(7) Uiso 1 1 d . . .
H2 H -0.165(4) 0.570(2) 0.5016(15) 0.095(6) 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
C8 0.0533(8) 0.0700(9) 0.0514(7) -0.0017(7) 0.0076(7) -0.0057(7)
C7 0.0434(6) 0.0599(7) 0.0357(6) 0.0003(5) -0.0002(5) 0.0019(6)
C6 0.0455(6) 0.0563(8) 0.0401(6) 0.0039(5) -0.0064(5) 0.0023(6)
C5 0.0534(8) 0.0632(9) 0.0527(8) 0.0084(7) -0.0039(6) -0.0025(7)
O1 0.0555(6) 0.0810(7) 0.0865(8) 0.0050(6) 0.0174(5) -0.0128(6)
N1 0.0528(6) 0.0662(7) 0.0607(7) -0.0104(6) 0.0116(6) -0.0009(6)
C1 0.0570(9) 0.0687(9) 0.0509(7) -0.0035(7) 0.0000(7) 0.0081(7)
N2 0.0672(8) 0.0680(9) 0.0628(8) -0.0175(7) 0.0082(6) 0.0005(6)
C4 0.0824(11) 0.0634(10) 0.0836(12) 0.0128(9) -0.0121(10) -0.0128(9)
C2 0.0805(12) 0.0659(10) 0.0749(11) -0.0095(8) -0.0041(9) 0.0179(11)
C9 0.0689(9) 0.0624(9) 0.0586(8) -0.0066(7) -0.0019(7) -0.0110(8)
C3 0.1100(15) 0.0535(10) 0.0860(12) -0.0057(9) -0.0221(12) 0.0134(10)

_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
C8 C9 1.359(2) . ?
C8 C7 1.399(2) . ?
C7 N1 1.3357(17) . ?
C7 C6 1.4715(19) . ?
C6 C1 1.396(2) . ?
C6 C5 1.406(2) . ?
C5 O1 1.3655(18) . ?
C5 C4 1.383(3) . ?
N1 N2 1.3417(17) . ?
C1 C2 1.372(2) . ?
N2 C9 1.329(2) . ?
C4 C3 1.379(3) . ?
C2 C3 1.377(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
C9 C8 C7 105.32(13) . . ?
N1 C7 C8 109.92(12) . . ?
N1 C7 C6 119.83(12) . . ?
C8 C7 C6 130.25(12) . . ?
C1 C6 C5 118.28(14) . . ?
C1 C6 C7 120.66(12) . . ?
C5 C6 C7 121.05(12) . . ?
O1 C5 C4 118.30(15) . . ?
O1 C5 C6 121.55(14) . . ?
C4 C5 C6 120.15(16) . . ?
C7 N1 N2 105.33(11) . . ?
C2 C1 C6 121.36(17) . . ?
C9 N2 N1 111.97(13) . . ?
C3 C4 C5 119.73(19) . . ?
C1 C2 C3 119.33(18) . . ?
N2 C9 C8 107.46(15) . . ?
C2 C3 C4 121.13(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1479796'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F N2 O'
_chemical_formula_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17

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'
F F 0.0171 0.0103 '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                   3.7769(5)
_cell_length_b                   10.7326(13)
_cell_length_c                   19.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     785.87(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    994
_cell_measurement_theta_min      2.8315
_cell_measurement_theta_max      22.9009

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4740
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.28
_reflns_number_total             1832
_reflns_number_gt                1496
_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 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)+(0.0538P)²+0.0678P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(16)
_refine_ls_number_reflns         1832
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
N1 N 0.2329(6) 0.28105(18) 0.81739(9) 0.0295(5) Uani 1 1 d . . .
O1 O 0.4143(5) 0.06724(16) 0.76481(8) 0.0354(5) Uani 1 1 d . . .
C3 C 0.2891(7) 0.0135(2) 0.82390(11) 0.0284(5) Uani 1 1 d . . .
F1 F 0.2305(5) -0.29724(13) 0.89300(9) 0.0567(5) Uani 1 1 d . . .
C4 C 0.1404(6) 0.0842(2) 0.87738(11) 0.0237(5) Uani 1 1 d . . .
C8 C 0.0221(7) 0.0207(2) 0.93619(11) 0.0298(6) Uani 1 1 d . . .
C9 C 0.0531(7) -0.1073(2) 0.94259(14) 0.0344(6) Uani 1 1 d . . .
N2 N 0.1649(6) 0.40306(19) 0.82981(11) 0.0319(5) Uani 1 1 d . . .
C7 C -0.0422(7) 0.3051(2) 0.91973(12) 0.0301(6) Uani 1 1 d . . .
C2 C 0.3145(8) -0.1147(2) 0.82895(13) 0.0337(6) Uani 1 1 d . . .
C1 C 0.1969(7) -0.1708(2) 0.88815(13) 0.0360(6) Uani 1 1 d . . .
C5 C 0.1068(6) 0.2209(2) 0.87282(11) 0.0250(5) Uani 1 1 d . . .
C6 C 0.0010(7) 0.4199(2) 0.89040(13) 0.0328(6) Uani 1 1 d . . .
H6 H -0.085(6) 0.0701(19) 0.9753(11) 0.024(6) Uiso 1 1 d . . .
H5 H -0.149(7) 0.288(2) 0.9630(12) 0.031(7) Uiso 1 1 d . . .
H2 H 0.398(10) 0.149(3) 0.7703(17) 0.071(11) Uiso 1 1 d . . .
H4 H -0.057(8) 0.502(2) 0.9062(12) 0.039(7) Uiso 1 1 d . . .
H7 H -0.033(9) -0.147(2) 0.9822(14) 0.044(8) Uiso 1 1 d . . .
H3 H 0.238(9) 0.465(2) 0.7978(13) 0.045(8) Uiso 1 1 d . . .
H1 H 0.406(9) -0.165(2) 0.7944(15) 0.051(9) 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
N1 0.0374(12) 0.0266(11) 0.0246(11) 0.0025(8) -0.0002(9) 0.0002(9)
O1 0.0537(12) 0.0258(10) 0.0266(9) -0.0004(7) 0.0120(8) 0.0001(8)
C3 0.0320(13) 0.0310(13) 0.0223(11) 0.0014(9) 0.0002(11) -0.0028(10)
F1 0.0927(14) 0.0232(8) 0.0543(11) 0.0055(7) 0.0018(10) -0.0021(9)
C4 0.0247(11) 0.0235(12) 0.0231(11) 0.0018(8) -0.0041(9) -0.0032(9)
C8 0.0309(14) 0.0354(14) 0.0231(12) -0.0014(10) 0.0022(10) -0.0028(10)
C9 0.0421(16) 0.0351(13) 0.0259(12) 0.0085(11) 0.0004(11) -0.0089(12)
N2 0.0434(13) 0.0228(10) 0.0294(11) 0.0020(8) -0.0010(10) -0.0003(9)
C7 0.0302(14) 0.0345(14) 0.0257(12) -0.0017(10) -0.0001(10) 0.0007(11)
C2 0.0423(16) 0.0301(13) 0.0288(13) -0.0053(10) 0.0004(12) 0.0005(11)
C1 0.0488(16) 0.0249(13) 0.0342(14) 0.0038(10) -0.0036(13) -0.0028(11)
C5 0.0234(12) 0.0292(12) 0.0222(11) 0.0011(9) -0.0008(10) -0.0020(9)
C6 0.0337(13) 0.0298(13) 0.0348(13) -0.0026(11) -0.0021(11) 0.0028(11)

_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 C5 1.341(3) . ?
N1 N2 1.356(3) . ?
O1 C3 1.367(3) . ?
C3 C2 1.383(3) . ?
C3 C4 1.402(3) . ?
F1 C1 1.366(3) . ?
C4 C8 1.402(3) . ?
C4 C5 1.475(3) . ?
C8 C9 1.384(3) . ?
C9 C1 1.369(4) . ?
N2 C6 1.340(3) . ?
C7 C6 1.366(4) . ?
C7 C5 1.401(3) . ?
C2 C1 1.370(4) . ?

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
C5 N1 N2 104.82(19) . . ?
O1 C3 C2 117.1(2) . . ?
O1 C3 C4 122.0(2) . . ?
C2 C3 C4 120.9(2) . . ?
C8 C4 C3 117.8(2) . . ?
C8 C4 C5 120.4(2) . . ?
C3 C4 C5 121.88(19) . . ?
C9 C8 C4 121.9(2) . . ?
C1 C9 C8 117.3(2) . . ?
C6 N2 N1 111.90(19) . . ?
C6 C7 C5 105.3(2) . . ?
C1 C2 C3 118.3(2) . . ?
F1 C1 C2 117.7(2) . . ?
F1 C1 C9 118.6(2) . . ?
C2 C1 C9 123.7(2) . . ?
N1 C5 C7 110.6(2) . . ?
N1 C5 C4 119.8(2) . . ?
C7 C5 C4 129.6(2) . . ?
N2 C6 C7 107.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1479797'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   5.6704(11)
_cell_length_b                   10.076(2)
_cell_length_c                   16.296(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     931.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6733
_cell_measurement_theta_min      3.045
_cell_measurement_theta_max      27.525

_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9076
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2127
_reflns_number_gt                1738
_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 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)+(0.0736P)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    mixed
_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   2.4(12)
_refine_ls_number_reflns         2127
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_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 0.99578(17) 0.27073(12) 0.19898(6) 0.0483(3) Uani 1 1 d . . .
N1 N 0.7443(2) 0.48456(14) 0.20183(8) 0.0485(3) Uani 1 1 d . . .
C5 C 0.6262(2) 0.28756(14) 0.12596(7) 0.0354(3) Uani 1 1 d . . .
O2 O 0.7026(2) -0.10792(12) 0.05547(7) 0.0572(3) Uani 1 1 d . . .
C2 C 0.6881(3) 0.02199(15) 0.07989(8) 0.0426(3) Uani 1 1 d . . .
C4 C 0.8250(2) 0.21570(15) 0.15059(8) 0.0377(3) Uani 1 1 d . . .
C9 C 0.4628(2) 0.22139(16) 0.07601(8) 0.0417(3) Uani 1 1 d . . .
H9 H 0.3308 0.2674 0.0576 0.050 Uiso 1 1 calc R . .
C10 C 0.4908(3) 0.09139(16) 0.05328(8) 0.0457(4) Uani 1 1 d . . .
H10 H 0.3787 0.0501 0.0204 0.055 Uiso 1 1 calc R . .
C3 C 0.8564(3) 0.08383(15) 0.12808(8) 0.0424(3) Uani 1 1 d . . .
H3 H 0.9895 0.0375 0.1452 0.051 Uiso 1 1 calc R . .
C6 C 0.5886(2) 0.42556(15) 0.15204(7) 0.0370(3) Uani 1 1 d . . .
C7 C 0.4039(3) 0.51414(17) 0.13401(8) 0.0472(4) Uani 1 1 d . . .
H7 H 0.2731 0.4983 0.1010 0.057 Uiso 1 1 calc R . .
C1 C 0.9154(4) -0.17709(19) 0.07085(11) 0.0659(5) Uani 1 1 d . . .
H1A H 1.0452 -0.1285 0.0479 0.099 Uiso 1 1 calc R . .
H1B H 0.9078 -0.2634 0.0461 0.099 Uiso 1 1 calc R . .
H1C H 0.9376 -0.1862 0.1290 0.099 Uiso 1 1 calc R . .
N2 N 0.6599(2) 0.60732(14) 0.21468(8) 0.0511(3) Uani 1 1 d . . .
H2 H 0.7283 0.6658 0.2449 0.061 Uiso 1 1 calc R . .
C8 C 0.4572(3) 0.62774(17) 0.17498(10) 0.0514(4) Uani 1 1 d . . .
H8 H 0.3687 0.7054 0.1753 0.062 Uiso 1 1 calc R . .
H20 H 0.957(3) 0.356(2) 0.2081(10) 0.066(6) 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 0.0399(5) 0.0422(6) 0.0628(7) -0.0062(5) -0.0182(5) 0.0017(5)
N1 0.0458(6) 0.0423(8) 0.0575(7) -0.0079(6) -0.0130(6) 0.0015(5)
C5 0.0333(6) 0.0402(7) 0.0328(6) -0.0004(5) 0.0019(5) -0.0036(5)
O2 0.0669(7) 0.0404(6) 0.0643(7) -0.0119(5) -0.0022(6) -0.0045(5)
C2 0.0487(8) 0.0391(8) 0.0400(6) -0.0036(6) 0.0065(6) -0.0063(6)
C4 0.0344(6) 0.0411(8) 0.0374(6) -0.0004(6) -0.0007(6) -0.0047(5)
C9 0.0339(6) 0.0506(9) 0.0405(7) -0.0012(6) -0.0020(6) -0.0021(6)
C10 0.0436(7) 0.0503(9) 0.0431(7) -0.0092(6) -0.0035(6) -0.0105(7)
C3 0.0408(7) 0.0411(8) 0.0454(7) -0.0008(6) -0.0029(6) 0.0018(6)
C6 0.0346(6) 0.0438(8) 0.0328(6) 0.0003(5) 0.0013(5) -0.0015(5)
C7 0.0438(7) 0.0523(9) 0.0454(7) -0.0021(7) -0.0080(6) 0.0044(7)
C1 0.0751(12) 0.0468(10) 0.0757(12) -0.0088(8) 0.0028(10) 0.0054(9)
N2 0.0546(8) 0.0415(7) 0.0570(7) -0.0095(6) -0.0101(6) 0.0033(6)
C8 0.0539(9) 0.0496(10) 0.0507(7) -0.0025(7) -0.0053(7) 0.0130(7)

_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 C4 1.3666(15) . ?
N1 C6 1.3385(19) . ?
N1 N2 1.343(2) . ?
C5 C4 1.3985(19) . ?
C5 C9 1.4020(18) . ?
C5 C6 1.470(2) . ?
O2 C2 1.3706(19) . ?
O2 C1 1.416(2) . ?
C2 C3 1.384(2) . ?
C2 C10 1.389(2) . ?
C4 C3 1.390(2) . ?
C9 C10 1.370(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.359(2) . ?
N2 C8 1.335(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
C6 N1 N2 105.57(13) . . ?
C4 C5 C9 116.94(13) . . ?
C4 C5 C6 121.59(12) . . ?
C9 C5 C6 121.47(13) . . ?
C2 O2 C1 118.04(13) . . ?
O2 C2 C3 123.58(14) . . ?
O2 C2 C10 116.02(13) . . ?
C3 C2 C10 120.40(14) . . ?
O1 C4 C3 116.69(13) . . ?
O1 C4 C5 121.79(13) . . ?
C3 C4 C5 121.52(12) . . ?
C10 C9 C5 122.35(14) . . ?
C9 C10 C2 119.35(13) . . ?
C2 C3 C4 119.43(13) . . ?
N1 C6 C7 109.63(14) . . ?
N1 C6 C5 119.99(13) . . ?
C7 C6 C5 130.38(13) . . ?
C8 C7 C6 105.43(13) . . ?
C8 N2 N1 111.92(14) . . ?
N2 C8 C7 107.44(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1479798'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2 O'
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.7690(16)
_cell_length_b                   11.243(2)
_cell_length_c                   10.244(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.15(3)
_cell_angle_gamma                90.00
_cell_volume                     880.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7980
_cell_measurement_theta_min      3.215
_cell_measurement_theta_max      27.475

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8279
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1999
_reflns_number_gt                1508
_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 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)+(0.0684P)²+0.3009P] 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         1999
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C9 C 0.1651(3) -0.02111(19) 0.8818(2) 0.0475(5) Uani 1 1 d . . .
N1 N 0.4093(2) 0.19814(13) 1.11729(15) 0.0430(4) Uani 1 1 d . . .
C4 C 0.2655(2) 0.02156(15) 0.99935(17) 0.0345(4) Uani 1 1 d . . .
C3 C 0.3153(2) 0.14737(15) 1.00879(16) 0.0341(4) Uani 1 1 d . . .
C6 C 0.2604(3) -0.17765(16) 1.0880(2) 0.0436(5) Uani 1 1 d . . .
C5 C 0.3127(2) -0.05897(15) 1.10321(17) 0.0365(4) Uani 1 1 d . . .
N2 N 0.4387(2) 0.31550(13) 1.10274(16) 0.0479(4) Uani 1 1 d . . .
C7 C 0.1625(3) -0.21888(17) 0.9703(2) 0.0482(5) Uani 1 1 d . . .
C1 C 0.3604(3) 0.33920(17) 0.9800(2) 0.0462(5) Uani 1 1 d . . .
C8 C 0.1155(3) -0.1391(2) 0.8675(2) 0.0544(6) Uani 1 1 d . . .
C2 C 0.2826(3) 0.23858(17) 0.9165(2) 0.0456(5) Uani 1 1 d . . .
C10 C 0.1101(4) -0.3482(2) 0.9552(4) 0.0688(8) Uani 1 1 d . . .
O1 O 0.41073(19) -0.01897(11) 1.21867(12) 0.0496(4) Uani 1 1 d . . .
H9 H 0.4298 -0.0740 1.2717 0.074 Uiso 1 1 calc R . .
H10 H 0.451(3) 0.163(2) 1.187(2) 0.050(6) Uiso 1 1 d . . .
H3 H 0.130(3) 0.034(2) 0.812(2) 0.063(7) Uiso 1 1 d . . .
H8 H 0.295(3) -0.2308(19) 1.166(2) 0.051(6) Uiso 1 1 d . . .
H2 H 0.220(3) 0.234(2) 0.822(3) 0.064(7) Uiso 1 1 d . . .
H1 H 0.365(3) 0.4222(19) 0.948(2) 0.050(5) Uiso 1 1 d . . .
H4 H 0.047(3) -0.164(2) 0.781(2) 0.068(7) Uiso 1 1 d . . .
H6 H 0.148(4) -0.387(3) 0.875(4) 0.124(12) Uiso 1 1 d . . .
H5 H -0.015(4) -0.357(3) 0.942(3) 0.101(10) Uiso 1 1 d . . .
H7 H 0.158(5) -0.392(3) 1.031(3) 0.106(12) 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
C9 0.0467(11) 0.0487(11) 0.0434(11) -0.0044(9) -0.0019(9) 0.0022(9)
N1 0.0677(11) 0.0276(7) 0.0303(8) 0.0019(6) -0.0005(7) -0.0015(7)
C4 0.0356(8) 0.0326(8) 0.0353(9) -0.0055(7) 0.0059(7) 0.0026(6)
C3 0.0367(9) 0.0343(9) 0.0312(8) 0.0001(6) 0.0055(7) 0.0044(7)
C6 0.0490(11) 0.0331(9) 0.0504(11) -0.0032(8) 0.0133(9) -0.0002(8)
C5 0.0417(9) 0.0328(9) 0.0352(9) -0.0044(7) 0.0073(7) 0.0018(7)
N2 0.0723(11) 0.0279(8) 0.0425(9) -0.0006(6) 0.0078(8) -0.0034(7)
C7 0.0429(10) 0.0396(10) 0.0640(13) -0.0167(9) 0.0150(10) -0.0065(8)
C1 0.0591(12) 0.0328(9) 0.0457(10) 0.0084(8) 0.0067(9) 0.0057(8)
C8 0.0478(12) 0.0564(12) 0.0552(13) -0.0202(10) -0.0011(10) -0.0072(9)
C2 0.0514(11) 0.0435(10) 0.0386(10) 0.0070(8) -0.0009(8) 0.0061(8)
C10 0.0686(16) 0.0460(13) 0.094(2) -0.0265(14) 0.0199(16) -0.0177(11)
O1 0.0806(10) 0.0292(6) 0.0339(7) 0.0023(5) -0.0040(7) -0.0017(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C8 1.382(3) . ?
C9 C4 1.399(3) . ?
N1 C3 1.345(2) . ?
N1 N2 1.352(2) . ?
C4 C5 1.396(2) . ?
C4 C3 1.465(2) . ?
C3 C2 1.388(2) . ?
C6 C7 1.387(3) . ?
C6 C5 1.395(3) . ?
C5 O1 1.365(2) . ?
N2 C1 1.324(3) . ?
C7 C8 1.382(3) . ?
C7 C10 1.511(3) . ?
C1 C2 1.389(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
C8 C9 C4 121.5(2) . . ?
C3 N1 N2 113.64(15) . . ?
C5 C4 C9 117.74(17) . . ?
C5 C4 C3 123.02(16) . . ?
C9 C4 C3 119.24(17) . . ?
N1 C3 C2 104.91(16) . . ?
N1 C3 C4 124.27(15) . . ?
C2 C3 C4 130.83(17) . . ?
C7 C6 C5 121.38(19) . . ?
O1 C5 C6 121.24(17) . . ?
O1 C5 C4 118.57(15) . . ?
C6 C5 C4 120.19(17) . . ?
C1 N2 N1 104.05(15) . . ?
C8 C7 C6 118.44(18) . . ?
C8 C7 C10 121.1(2) . . ?
C6 C7 C10 120.5(2) . . ?
N2 C1 C2 111.72(17) . . ?
C9 C8 C7 120.72(19) . . ?
C3 C2 C1 105.68(17) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
