# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_ohhbdi-1
_database_code_depnum_ccdc_archive 'CCDC 1417289'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_audit_creation_date             2014-09-11
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H16N2O3
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   13.6811(11)
_cell_length_b                   11.8839(12)
_cell_length_c                   7.3549(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1195.80(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1133
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6640
_cell_measurement_theta_min      2.2630
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2588
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   74.00  109.00   1.0000  140.4000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   94.00   1.0000  140.4000
omega____ theta____ kappa____ phi______ frames
    -       27.3512   19.0000  -60.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0151596000
_diffrn_orient_matrix_UB_12      0.0559102000
_diffrn_orient_matrix_UB_13      -0.0189461000
_diffrn_orient_matrix_UB_21      -0.0494636000
_diffrn_orient_matrix_UB_22      0.0159037000
_diffrn_orient_matrix_UB_23      -0.0132933000
_diffrn_orient_matrix_UB_31      -0.0039988000
_diffrn_orient_matrix_UB_32      0.0135199000
_diffrn_orient_matrix_UB_33      0.0935474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_number_gt                1520
_reflns_number_total             1818
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.1083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1403
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H3A of C3, H1 of C1, H12 of C12, H2 of C2
 At 1.5 times of:
  {H4A,H4B,H4C} of C4, {H13A,H13B,H13C} of C13, H3 of O3, {H5A,H5B,H5C} of C5
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C1(H1), C2(H2), C3(H3A)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.05300(17) 0.5910(2) 0.0768(4) 0.0636(8) Uani 1 1 d . . .
O2 O 0.17471(18) 0.3103(2) 0.9587(4) 0.0633(7) Uani 1 1 d . . .
O3 O 0.40745(18) 0.4961(2) 0.4283(4) 0.0710(9) Uani 1 1 d . . .
H3 H 0.3787 0.5358 0.3546 0.107 Uiso 1 1 calc R . .
N4 N 0.20124(19) 0.6466(2) -0.0432(4) 0.0447(7) Uani 1 1 d . . .
N5 N 0.30654(18) 0.5829(2) 0.1642(4) 0.0443(7) Uani 1 1 d . . .
C6 C 0.1418(3) 0.5975(3) 0.0853(5) 0.0463(8) Uani 1 1 d . . .
C7 C 0.2405(2) 0.4563(3) 0.5292(4) 0.0379(7) Uani 1 1 d . . .
C8 C 0.2967(2) 0.6354(3) 0.0099(5) 0.0445(8) Uani 1 1 d . . .
C9 C 0.2116(2) 0.5561(3) 0.2245(4) 0.0414(8) Uani 1 1 d . . .
C10 C 0.2260(2) 0.3588(3) 0.8206(5) 0.0448(8) Uani 1 1 d . . .
C11 C 0.3424(2) 0.4540(3) 0.5502(5) 0.0456(8) Uani 1 1 d . . .
C12 C 0.1838(2) 0.4083(3) 0.6696(5) 0.0408(7) Uani 1 1 d . . .
H12 H 0.1160 0.4101 0.6603 0.049 Uiso 1 1 calc R . .
C1 C 0.3824(2) 0.4055(3) 0.7043(6) 0.0535(9) Uani 1 1 d . . .
H1 H 0.4500 0.4049 0.7178 0.064 Uiso 1 1 calc R . .
C2 C 0.1848(2) 0.5031(3) 0.3776(5) 0.0407(7) Uani 1 1 d . . .
H2 H 0.1176 0.4945 0.3896 0.049 Uiso 1 1 calc R . .
C3 C 0.3262(2) 0.3590(3) 0.8364(6) 0.0522(9) Uani 1 1 d . . .
H3A H 0.3556 0.3270 0.9381 0.063 Uiso 1 1 calc R . .
C4 C 0.1636(3) 0.6999(3) -0.2083(5) 0.0615(11) Uani 1 1 d . . .
H4A H 0.1150 0.6522 -0.2626 0.092 Uiso 1 1 calc R . .
H4B H 0.2162 0.7114 -0.2926 0.092 Uiso 1 1 calc R . .
H4C H 0.1347 0.7711 -0.1780 0.092 Uiso 1 1 calc R . .
C5 C 0.0711(3) 0.3039(4) 0.9407(6) 0.0671(11) Uani 1 1 d . . .
H5A H 0.0549 0.2654 0.8300 0.101 Uiso 1 1 calc R . .
H5B H 0.0442 0.3784 0.9380 0.101 Uiso 1 1 calc R . .
H5C H 0.0444 0.2634 1.0422 0.101 Uiso 1 1 calc R . .
C13 C 0.3792(3) 0.6782(3) -0.1008(5) 0.0578(10) Uani 1 1 d . . .
H13A H 0.3760 0.6462 -0.2205 0.087 Uiso 1 1 calc R . .
H13B H 0.4399 0.6573 -0.0445 0.087 Uiso 1 1 calc R . .
H13C H 0.3752 0.7586 -0.1092 0.087 Uiso 1 1 calc R . .


_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 C6 1.219(4) . ?
O2 C10 1.361(4) . ?
O2 C5 1.426(4) . ?
O3 C11 1.359(4) . ?
N4 C6 1.376(4) . ?
N4 C8 1.369(4) . ?
N4 C4 1.464(5) . ?
N5 C8 1.302(4) . ?
N5 C9 1.408(4) . ?
C6 C9 1.485(5) . ?
C7 C11 1.403(4) . ?
C7 C12 1.411(4) . ?
C7 C2 1.460(4) . ?
C8 C13 1.482(5) . ?
C9 C2 1.341(5) . ?
C10 C12 1.383(5) . ?
C10 C3 1.376(4) . ?
C11 C1 1.384(5) . ?
C1 C3 1.356(5) . ?

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
C10 O2 C5 117.8(3) . . ?
C6 N4 C4 123.0(3) . . ?
C8 N4 C6 109.1(3) . . ?
C8 N4 C4 127.9(3) . . ?
C8 N5 C9 106.7(3) . . ?
O1 C6 N4 125.5(3) . . ?
O1 C6 C9 131.0(3) . . ?
N4 C6 C9 103.5(3) . . ?
C11 C7 C12 117.2(3) . . ?
C11 C7 C2 127.5(3) . . ?
C12 C7 C2 115.2(3) . . ?
N4 C8 C13 122.4(3) . . ?
N5 C8 N4 113.2(3) . . ?
N5 C8 C13 124.4(3) . . ?
N5 C9 C6 107.5(3) . . ?
C2 C9 N5 128.5(3) . . ?
C2 C9 C6 124.0(3) . . ?
O2 C10 C12 124.3(3) . . ?
O2 C10 C3 116.8(3) . . ?
C3 C10 C12 118.8(3) . . ?
O3 C11 C7 124.9(3) . . ?
O3 C11 C1 115.7(3) . . ?
C1 C11 C7 119.4(3) . . ?
C10 C12 C7 122.1(3) . . ?
C3 C1 C11 122.2(3) . . ?
C9 C2 C7 132.7(3) . . ?
C1 C3 C10 120.3(3) . . ?

####################################################################### 
# 
# 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_omehbdi
_database_code_depnum_ccdc_archive 'CCDC 1417290'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O3'
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29

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   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   8.3642(5)
_cell_length_b                   7.8279(5)
_cell_length_c                   20.8234(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.819(6)
_cell_angle_gamma                90.00
_cell_volume                     1363.25(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            red
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.090
_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      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  'multiwire proportional'
_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            4942
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2901
_reflns_number_gt                2092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0684P)²+0.9624P] 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         2901
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2220
_refine_ls_wR_factor_gt          0.2087
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.011

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 0.6255(3) 0.4991(4) 0.26839(12) 0.0961(9) Uani 1 1 d . . .
O2 O 0.0551(3) 0.4869(3) 0.13200(13) 0.0864(8) Uani 1 1 d . . .
O3 O 0.2862(4) 0.1919(4) -0.05287(13) 0.1016(9) Uani 1 1 d . . .
N1 N 0.6067(3) 0.3013(4) 0.05198(12) 0.0644(7) Uani 1 1 d . . .
C12 C -0.0873(5) 0.5621(6) 0.1564(3) 0.1190(18) Uani 1 1 d . . .
H12A H -0.1170 0.5046 0.1952 0.179 Uiso 1 1 calc R . .
H12B H -0.1720 0.5513 0.1251 0.179 Uiso 1 1 calc R . .
H12C H -0.0686 0.6808 0.1653 0.179 Uiso 1 1 calc R . .
C1 C 0.6414(7) 0.5782(7) 0.3293(2) 0.130(2) Uani 1 1 d . . .
H1A H 0.6139 0.6969 0.3256 0.196 Uiso 1 1 calc R . .
H1B H 0.7499 0.5676 0.3444 0.196 Uiso 1 1 calc R . .
H1C H 0.5712 0.5236 0.3590 0.196 Uiso 1 1 calc R . .
C2 C 0.4792(4) 0.5046(4) 0.23797(15) 0.0675(9) Uani 1 1 d . . .
C3 C 0.4727(3) 0.4338(4) 0.17710(14) 0.0583(7) Uani 1 1 d . . .
H3 H 0.5654 0.3889 0.1596 0.070 Uiso 1 1 calc R . .
C4 C 0.3311(3) 0.4279(4) 0.14134(14) 0.0539(7) Uani 1 1 d . . .
C5 C 0.3222(3) 0.3534(4) 0.07732(14) 0.0567(7) Uani 1 1 d . . .
H5 H 0.2197 0.3420 0.0600 0.068 Uiso 1 1 calc R . .
C6 C 0.4412(3) 0.2984(4) 0.03948(13) 0.0539(7) Uani 1 1 d . . .
C7 C 0.6712(4) 0.2382(5) 0.00066(15) 0.0700(9) Uani 1 1 d . . .
C8 C 0.8470(5) 0.2178(7) -0.0069(2) 0.1086(16) Uani 1 1 d . . .
H8A H 0.9016 0.2661 0.0297 0.163 Uiso 1 1 calc R . .
H8B H 0.8800 0.2755 -0.0451 0.163 Uiso 1 1 calc R . .
H8C H 0.8726 0.0986 -0.0101 0.163 Uiso 1 1 calc R . .
C9 C 0.3420(5) 0.5732(4) 0.26348(17) 0.0769(10) Uani 1 1 d . . .
H9 H 0.3456 0.6227 0.3041 0.092 Uiso 1 1 calc R . .
C10 C 0.2002(5) 0.5689(4) 0.22936(18) 0.0776(10) Uani 1 1 d . . .
H10 H 0.1085 0.6150 0.2472 0.093 Uiso 1 1 calc R . .
C11 C 0.1924(4) 0.4973(4) 0.16905(16) 0.0636(8) Uani 1 1 d . . .
N2 N 0.5630(4) 0.1907(3) -0.04655(12) 0.0710(8) Uani 1 1 d . . .
C13 C 0.4115(5) 0.2232(4) -0.02435(16) 0.0686(9) Uani 1 1 d . . .
C14 C 0.5945(6) 0.1198(5) -0.10987(17) 0.1013(14) Uani 1 1 d . . .
H14A H 0.6919 0.1673 -0.1259 0.152 Uiso 1 1 calc R . .
H14B H 0.5076 0.1476 -0.1386 0.152 Uiso 1 1 calc R . .
H14C H 0.6047 -0.0020 -0.1067 0.152 Uiso 1 1 calc R . .


_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 C2 1.371(4) . ?
O1 C1 1.415(5) . ?
O2 C11 1.377(4) . ?
O2 C12 1.428(4) . ?
O3 C13 1.222(4) . ?
N1 C7 1.302(4) . ?
N1 C6 1.404(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C9 1.380(5) . ?
C2 C3 1.384(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C11 1.412(4) . ?
C4 C5 1.456(4) . ?
C5 C6 1.349(4) . ?
C5 H5 0.9300 . ?
C6 C13 1.472(4) . ?
C7 N2 1.378(4) . ?
C7 C8 1.489(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9300 . ?
N2 C13 1.379(4) . ?
N2 C14 1.458(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C2 O1 C1 118.2(3) . . ?
C11 O2 C12 118.0(3) . . ?
C7 N1 C6 105.1(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C9 125.2(3) . . ?
O1 C2 C3 115.7(3) . . ?
C9 C2 C3 119.1(3) . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C11 117.8(3) . . ?
C3 C4 C5 122.4(2) . . ?
C11 C4 C5 119.8(3) . . ?
C6 C5 C4 129.4(3) . . ?
C6 C5 H5 115.3 . . ?
C4 C5 H5 115.3 . . ?
C5 C6 N1 128.3(3) . . ?
C5 C6 C13 122.6(3) . . ?
N1 C6 C13 109.1(3) . . ?
N1 C7 N2 114.3(3) . . ?
N1 C7 C8 123.3(4) . . ?
N2 C7 C8 122.4(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C2 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C2 C9 H9 119.7 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 O2 124.3(3) . . ?
C10 C11 C4 120.1(3) . . ?
O2 C11 C4 115.6(3) . . ?
C7 N2 C13 108.0(3) . . ?
C7 N2 C14 128.5(3) . . ?
C13 N2 C14 123.5(3) . . ?
O3 C13 N2 125.9(3) . . ?
O3 C13 C6 130.7(3) . . ?
N2 C13 C6 103.4(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
