# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl_compound_4a
_database_code_depnum_ccdc_archive 'CCDC 1482293'
_audit_update_record             
;
2016-05-27 deposited with the CCDC.
2016-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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'
Cu Cu 0.3201 1.2651 '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   'P n a 21'
_symmetry_space_hall_group_name  'P 2c -2n'

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

_cell_length_a                   9.1004(11)
_cell_length_b                   10.5785(19)
_cell_length_c                   11.775(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1133.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    509
_cell_measurement_theta_min      3.4157
_cell_measurement_theta_max      28.9559

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies Lts.'
_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  'CrysAlisPro, Agilent Technologies Lts.'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3405
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         29.02
_reflns_number_total             1805
_reflns_number_gt                1157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis Pro, Agilent Technologies'
_computing_cell_refinement       'CrysAlis Pro, Agilent Technologies'
_computing_data_reduction        'CrysAlis Pro, Agilent Technologies'
_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)+(0.0291P)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     SHELXL
_refine_ls_extinction_coef       0.0153(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_number_reflns         1805
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.87643(17) 0.7236(2) 0.4790(2) 0.0580(7) Uani 1 1 d . . .
C10 C 0.8678(3) 0.5333(3) 0.7866(3) 0.0631(10) Uani 1 1 d . . .
H10 H 0.7870 0.4796 0.7899 0.076 Uiso 1 1 calc R . .
C3 C 0.8797(4) 0.8014(5) 0.1269(3) 0.0717(12) Uani 1 1 d . . .
H3 H 0.8064 0.7575 0.0885 0.086 Uiso 1 1 calc R . .
C11 C 0.9343(4) 0.5704(4) 0.8852(3) 0.0688(11) Uani 1 1 d . . .
H11 H 0.8989 0.5430 0.9551 0.083 Uiso 1 1 calc R . .
N1 N 1.0922(3) 0.7010(3) 0.5731(2) 0.0484(8) Uani 1 1 d . . .
C13 C 1.1034(3) 0.6913(3) 0.7768(4) 0.0627(10) Uani 1 1 d . . .
H13 H 1.1842 0.7451 0.7746 0.075 Uiso 1 1 calc R . .
C8 C 1.0350(3) 0.6560(3) 0.6764(3) 0.0450(8) Uani 1 1 d . . .
N2 N 1.0899(3) 0.7827(3) 0.3942(2) 0.0488(8) Uani 1 1 d . . .
C4 C 0.9389(5) 0.9091(5) 0.0797(4) 0.0883(15) Uani 1 1 d . . .
H4 H 0.9072 0.9372 0.0090 0.106 Uiso 1 1 calc R . .
C12 C 1.0531(4) 0.6479(4) 0.8791(3) 0.0757(12) Uani 1 1 d . . .
H12 H 1.1009 0.6718 0.9456 0.091 Uiso 1 1 calc R . .
C5 C 1.0449(5) 0.9743(5) 0.1378(4) 0.0885(15) Uani 1 1 d . . .
H5 H 1.0856 1.0469 0.1061 0.106 Uiso 1 1 calc R . .
C6 C 1.0914(3) 0.9333(4) 0.2423(4) 0.0661(11) Uani 1 1 d . . .
H6 H 1.1625 0.9788 0.2817 0.079 Uiso 1 1 calc R . .
C9 C 0.9181(3) 0.5741(3) 0.6823(3) 0.0527(9) Uani 1 1 d . . .
H9 H 0.8730 0.5461 0.6161 0.063 Uiso 1 1 calc R . .
C2 C 0.9283(3) 0.7583(4) 0.2308(3) 0.0534(9) Uani 1 1 d . . .
H2 H 0.8904 0.6842 0.2616 0.064 Uiso 1 1 calc R . .
C1 C 1.0338(3) 0.8261(3) 0.2885(3) 0.0461(8) Uani 1 1 d . . .
C7 C 1.0109(3) 0.7350(3) 0.4804(3) 0.0431(7) Uani 1 1 d . . .
HN2 H 1.183(3) 0.787(3) 0.409(3) 0.058(11) Uiso 1 1 d . . .
HN1 H 1.182(3) 0.726(3) 0.574(3) 0.058(11) 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 0.0248(8) 0.096(2) 0.0527(14) 0.0024(14) -0.0045(11) 0.0012(10)
C10 0.060(2) 0.057(2) 0.072(3) 0.010(2) 0.005(2) -0.0026(16)
C3 0.063(2) 0.100(4) 0.052(3) -0.005(3) -0.015(2) 0.014(2)
C11 0.087(3) 0.067(3) 0.052(3) 0.014(2) 0.010(2) 0.006(2)
N1 0.0292(14) 0.069(2) 0.0464(19) 0.0052(16) -0.0051(14) -0.0021(14)
C13 0.063(2) 0.074(3) 0.052(2) 0.001(2) -0.010(2) -0.0125(17)
C8 0.0367(16) 0.052(2) 0.046(2) -0.0036(19) -0.0029(17) 0.0061(14)
N2 0.0278(14) 0.074(2) 0.0444(19) 0.0074(16) -0.0056(14) -0.0006(14)
C4 0.094(3) 0.109(4) 0.062(3) 0.032(3) -0.011(3) 0.024(3)
C12 0.090(3) 0.088(3) 0.049(3) 0.002(2) -0.011(2) -0.011(2)
C5 0.095(3) 0.083(3) 0.088(4) 0.041(3) 0.000(3) 0.006(3)
C6 0.062(2) 0.057(2) 0.079(3) 0.010(2) -0.004(2) 0.0048(18)
C9 0.0477(18) 0.059(2) 0.052(2) 0.000(2) -0.0018(17) -0.0045(16)
C2 0.0462(18) 0.064(2) 0.050(2) 0.0006(18) -0.0067(18) 0.0069(16)
C1 0.0336(16) 0.059(2) 0.046(2) 0.0007(19) -0.0015(16) 0.0084(15)
C7 0.0299(13) 0.055(2) 0.0445(18) -0.0064(17) -0.0059(19) 0.0038(14)

_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 C7 1.230(3) . ?
C10 C11 1.366(5) . ?
C10 C9 1.380(5) . ?
C10 H10 0.9300 . ?
C3 C4 1.377(6) . ?
C3 C2 1.379(5) . ?
C3 H3 0.9300 . ?
C11 C12 1.359(5) . ?
C11 H11 0.9300 . ?
N1 C7 1.367(4) . ?
N1 C8 1.405(5) . ?
N1 HN1 0.86(3) . ?
C13 C12 1.368(5) . ?
C13 C8 1.388(5) . ?
C13 H13 0.9300 . ?
C8 C9 1.374(4) . ?
N2 C7 1.342(4) . ?
N2 C1 1.422(4) . ?
N2 HN2 0.87(3) . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C1 1.363(5) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C2 C1 1.378(5) . ?
C2 H2 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
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C12 C11 C10 118.8(4) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C7 N1 C8 125.4(3) . . ?
C7 N1 HN1 116(2) . . ?
C8 N1 HN1 116(2) . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C9 C8 C13 118.3(3) . . ?
C9 C8 N1 123.0(3) . . ?
C13 C8 N1 118.7(3) . . ?
C7 N2 C1 126.2(3) . . ?
C7 N2 HN2 113(2) . . ?
C1 N2 HN2 120(2) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.2(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C6 C1 C2 120.3(4) . . ?
C6 C1 N2 118.7(3) . . ?
C2 C1 N2 120.9(3) . . ?
O1 C7 N2 124.0(3) . . ?
O1 C7 N1 121.6(4) . . ?
N2 C7 N1 114.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.869
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.129
_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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1482294'
_audit_update_record             
;
2016-05-27 deposited with the CCDC.
2016-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O2'
_chemical_formula_sum            'C7 H5 N O2'
_chemical_formula_weight         135.12

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   P2(1)2(1)2(1)

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

_cell_length_a                   4.4436(14)
_cell_length_b                   6.641(2)
_cell_length_c                   20.957(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     618.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1585
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      24.94

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.108
_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      273(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            3269
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.25
_reflns_number_total             1471
_reflns_number_gt                1322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0518P)²+0.0364P] 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(15)
_refine_ls_number_reflns         1471
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_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 0.3521(2) 0.81059(15) 0.12378(5) 0.0545(3) Uani 1 1 d . . .
N1 N 0.2463(3) 0.5733(2) 0.19359(6) 0.0535(3) Uani 1 1 d . . .
H1 H 0.1701 0.5119 0.2259 0.064 Uiso 1 1 calc R . .
C1 C 0.5125(3) 0.63982(19) 0.10785(7) 0.0449(3) Uani 1 1 d . . .
C2 C 0.4491(3) 0.4899(2) 0.15092(7) 0.0455(3) Uani 1 1 d . . .
O2 O 0.0193(3) 0.8862(2) 0.20110(7) 0.0813(4) Uani 1 1 d . . .
C3 C 0.5786(4) 0.3018(2) 0.14505(8) 0.0584(4) Uani 1 1 d . . .
H3 H 0.5365 0.1985 0.1737 0.070 Uiso 1 1 calc R . .
C4 C 0.1861(4) 0.7650(2) 0.17690(7) 0.0552(4) Uani 1 1 d . . .
C5 C 0.7734(4) 0.2750(3) 0.09455(9) 0.0673(5) Uani 1 1 d . . .
H5 H 0.8658 0.1505 0.0892 0.081 Uiso 1 1 calc R . .
C6 C 0.7049(4) 0.6147(3) 0.05750(7) 0.0583(4) Uani 1 1 d . . .
H6 H 0.7453 0.7180 0.0288 0.070 Uiso 1 1 calc R . .
C7 C 0.8356(4) 0.4268(3) 0.05179(9) 0.0679(5) Uani 1 1 d . . .
H7 H 0.9683 0.4024 0.0184 0.081 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0623(6) 0.0469(5) 0.0544(6) 0.0040(4) 0.0068(5) 0.0054(5)
N1 0.0593(7) 0.0579(7) 0.0433(6) 0.0039(5) 0.0064(6) -0.0051(6)
C1 0.0437(7) 0.0455(6) 0.0456(7) -0.0004(5) -0.0030(5) -0.0027(5)
C2 0.0439(6) 0.0487(7) 0.0438(7) -0.0015(6) -0.0061(6) -0.0069(6)
O2 0.0926(9) 0.0820(8) 0.0693(8) -0.0149(6) 0.0140(7) 0.0258(8)
C3 0.0632(9) 0.0443(7) 0.0676(10) 0.0026(7) -0.0151(8) -0.0043(7)
C4 0.0595(8) 0.0581(8) 0.0478(8) -0.0069(6) 0.0017(7) 0.0045(7)
C5 0.0592(9) 0.0580(9) 0.0848(12) -0.0206(9) -0.0140(9) 0.0119(8)
C6 0.0522(8) 0.0708(10) 0.0520(8) 0.0043(7) 0.0050(7) -0.0008(8)
C7 0.0508(8) 0.0890(13) 0.0639(10) -0.0210(9) 0.0019(8) 0.0066(9)

_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 1.3694(19) . ?
O1 C1 1.3802(16) . ?
N1 C4 1.347(2) . ?
N1 C2 1.3854(18) . ?
N1 H1 0.8600 . ?
C1 C6 1.368(2) . ?
C1 C2 1.373(2) . ?
C2 C3 1.381(2) . ?
O2 C4 1.2059(19) . ?
C3 C5 1.379(3) . ?
C3 H3 0.9300 . ?
C5 C7 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 H7 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
C4 O1 C1 107.04(11) . . ?
C4 N1 C2 109.86(12) . . ?
C4 N1 H1 125.1 . . ?
C2 N1 H1 125.1 . . ?
C6 C1 C2 123.12(14) . . ?
C6 C1 O1 127.54(13) . . ?
C2 C1 O1 109.34(12) . . ?
C1 C2 C3 120.80(14) . . ?
C1 C2 N1 105.51(12) . . ?
C3 C2 N1 133.68(13) . . ?
C5 C3 C2 116.53(15) . . ?
C5 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
O2 C4 N1 130.05(17) . . ?
O2 C4 O1 121.70(16) . . ?
N1 C4 O1 108.25(13) . . ?
C7 C5 C3 122.08(16) . . ?
C7 C5 H5 119.0 . . ?
C3 C5 H5 119.0 . . ?
C1 C6 C7 116.09(16) . . ?
C1 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
C5 C7 C6 121.37(16) . . ?
C5 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?

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
C4 O1 C1 C6 178.96(15) . . . . ?
C4 O1 C1 C2 -0.51(16) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
O1 C1 C2 C3 179.13(12) . . . . ?
C6 C1 C2 N1 -179.56(14) . . . . ?
O1 C1 C2 N1 -0.06(15) . . . . ?
C4 N1 C2 C1 0.63(16) . . . . ?
C4 N1 C2 C3 -178.41(16) . . . . ?
C1 C2 C3 C5 0.5(2) . . . . ?
N1 C2 C3 C5 179.42(15) . . . . ?
C2 N1 C4 O2 178.78(17) . . . . ?
C2 N1 C4 O1 -0.96(17) . . . . ?
C1 O1 C4 O2 -178.87(15) . . . . ?
C1 O1 C4 N1 0.90(16) . . . . ?
C2 C3 C5 C7 -0.4(2) . . . . ?
C2 C1 C6 C7 0.0(2) . . . . ?
O1 C1 C6 C7 -179.35(14) . . . . ?
C3 C5 C7 C6 0.1(3) . . . . ?
C1 C6 C7 C5 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
