# 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_o
_database_code_depnum_ccdc_archive 'CCDC 1434472'
_audit_update_record             
;
2015-10-31 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Cl N2 O'
_chemical_formula_weight         274.74

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'
Cl Cl 0.1484 0.1585 '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                   6.0936(12)
_cell_length_b                   8.4244(17)
_cell_length_c                   26.374(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1353.9(5)
_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       Prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.275
_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  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4861
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2524
_reflns_number_gt                1706
_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)+(0.0308P)²+0.9255P] 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   0.64(18)
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.009

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
Cl1 Cl 0.5332(3) 0.5967(2) 0.23997(6) 0.0712(5) Uani 1 1 d . . .
C6 C 0.2375(9) 0.2987(6) 0.1419(2) 0.0405(13) Uani 1 1 d . . .
O1 O -0.1141(7) 0.1729(6) 0.14705(15) 0.0659(13) Uani 1 1 d . . .
H1 H -0.0781 0.1484 0.1181 0.099 Uiso 1 1 calc R . .
N1 N 0.1484(7) 0.1345(5) 0.07222(16) 0.0425(12) Uani 1 1 d . . .
C5 C 0.0396(9) 0.2714(6) 0.16722(19) 0.0413(13) Uani 1 1 d . . .
C15 C 0.0706(9) -0.3319(7) -0.1207(2) 0.0657(19) Uani 1 1 d . . .
H5A H 0.0489 -0.4050 -0.0932 0.099 Uiso 1 1 calc R . .
H5B H 0.1154 -0.3892 -0.1504 0.099 Uiso 1 1 calc R . .
H5C H -0.0641 -0.2769 -0.1275 0.099 Uiso 1 1 calc R . .
C1 C 0.3923(9) 0.3998(7) 0.16478(19) 0.0465(14) Uani 1 1 d . . .
H6 H 0.5260 0.4194 0.1490 0.056 Uiso 1 1 calc R . .
C3 C 0.1484(10) 0.4434(6) 0.2351(2) 0.0475(15) Uani 1 1 d . . .
H7 H 0.1187 0.4932 0.2658 0.057 Uiso 1 1 calc R . .
N2 N 0.2392(7) -0.2182(6) -0.10706(17) 0.0499(13) Uani 1 1 d . . .
C4 C -0.0040(10) 0.3428(6) 0.21369(19) 0.0486(15) Uani 1 1 d . . .
H9 H -0.1357 0.3227 0.2303 0.058 Uiso 1 1 calc R . .
C2 C 0.3450(10) 0.4697(6) 0.2107(2) 0.0448(14) Uani 1 1 d . . .
C11 C 0.2150(9) -0.1266(6) -0.0643(2) 0.0413(14) Uani 1 1 d . . .
C9 C 0.0148(9) -0.0440(6) 0.00976(19) 0.0472(15) Uani 1 1 d . . .
H12 H -0.1103 -0.0524 0.0298 0.057 Uiso 1 1 calc R . .
C12 C 0.3813(9) -0.0227(6) -0.04859(19) 0.0466(15) Uani 1 1 d . . .
H13 H 0.5070 -0.0137 -0.0684 0.056 Uiso 1 1 calc R . .
C8 C 0.1803(9) 0.0556(6) 0.0253(2) 0.0394(13) Uani 1 1 d . . .
C7 C 0.2883(10) 0.2266(7) 0.09329(19) 0.0436(14) Uani 1 1 d . . .
H15 H 0.4219 0.2472 0.0775 0.052 Uiso 1 1 calc R . .
C13 C 0.3660(9) 0.0662(7) -0.00514(19) 0.0475(15) Uani 1 1 d . . .
H16 H 0.4801 0.1337 0.0040 0.057 Uiso 1 1 calc R . .
C10 C 0.0265(9) -0.1320(6) -0.03428(19) 0.0482(15) Uani 1 1 d . . .
H17 H -0.0915 -0.1951 -0.0440 0.058 Uiso 1 1 calc R . .
C14 C 0.4434(10) -0.2253(7) -0.1348(2) 0.0612(17) Uani 1 1 d . . .
H18A H 0.4677 -0.1260 -0.1517 0.092 Uiso 1 1 calc R . .
H18B H 0.4364 -0.3092 -0.1593 0.092 Uiso 1 1 calc R . .
H18C H 0.5618 -0.2452 -0.1116 0.092 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
Cl1 0.0714(10) 0.0740(11) 0.0682(10) -0.0288(9) -0.0037(9) -0.0106(10)
C6 0.048(3) 0.031(3) 0.043(3) 0.006(3) -0.007(3) 0.003(3)
O1 0.069(3) 0.070(3) 0.059(3) -0.019(2) 0.013(2) -0.028(2)
N1 0.054(3) 0.036(3) 0.038(3) -0.002(2) 0.003(2) 0.000(2)
C5 0.045(3) 0.032(3) 0.047(3) 0.010(3) 0.000(3) -0.002(3)
C15 0.060(4) 0.077(5) 0.060(4) -0.023(4) 0.003(4) -0.007(4)
C1 0.050(4) 0.051(4) 0.039(3) 0.003(3) 0.003(3) 0.000(3)
C3 0.073(4) 0.037(3) 0.033(3) -0.005(3) 0.002(3) 0.011(3)
N2 0.041(3) 0.059(3) 0.049(3) -0.015(3) 0.003(2) -0.003(3)
C4 0.055(4) 0.050(3) 0.041(3) 0.001(3) 0.018(3) 0.004(3)
C2 0.058(4) 0.031(3) 0.045(3) -0.006(3) -0.004(3) 0.010(3)
C11 0.050(3) 0.040(3) 0.034(3) 0.001(3) -0.003(3) 0.002(3)
C9 0.044(4) 0.056(4) 0.042(3) -0.002(3) 0.006(3) -0.005(3)
C12 0.048(3) 0.054(4) 0.038(3) 0.002(3) 0.013(3) -0.006(3)
C8 0.053(4) 0.030(3) 0.036(3) 0.000(2) 0.002(3) 0.003(3)
C7 0.053(4) 0.042(3) 0.035(3) 0.005(3) 0.009(3) 0.003(3)
C13 0.053(4) 0.044(4) 0.045(3) -0.007(3) 0.006(3) -0.015(3)
C10 0.039(3) 0.058(4) 0.048(3) -0.005(3) 0.000(3) -0.009(3)
C14 0.067(4) 0.068(4) 0.048(4) -0.011(3) 0.017(3) -0.006(4)

_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
Cl1 C2 1.747(6) . ?
C6 C5 1.398(7) . ?
C6 C1 1.407(7) . ?
C6 C7 1.452(7) . ?
O1 C5 1.360(6) . ?
N1 C7 1.280(6) . ?
N1 C8 1.418(6) . ?
C5 C4 1.391(7) . ?
C15 N2 1.450(7) . ?
C1 C2 1.378(7) . ?
C3 C4 1.378(7) . ?
C3 C2 1.377(7) . ?
N2 C11 1.374(6) . ?
N2 C14 1.444(7) . ?
C11 C10 1.397(7) . ?
C11 C12 1.402(7) . ?
C9 C8 1.374(7) . ?
C9 C10 1.380(6) . ?
C12 C13 1.372(7) . ?
C8 C13 1.390(7) . ?

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 C6 C1 118.2(5) . . ?
C5 C6 C7 122.5(5) . . ?
C1 C6 C7 119.3(5) . . ?
C7 N1 C8 124.9(5) . . ?
O1 C5 C4 118.5(5) . . ?
O1 C5 C6 120.5(5) . . ?
C4 C5 C6 121.0(5) . . ?
C2 C1 C6 119.7(5) . . ?
C4 C3 C2 119.7(5) . . ?
C11 N2 C14 122.0(5) . . ?
C11 N2 C15 119.9(5) . . ?
C14 N2 C15 117.2(5) . . ?
C3 C4 C5 119.9(5) . . ?
C1 C2 C3 121.5(5) . . ?
C1 C2 Cl1 120.8(5) . . ?
C3 C2 Cl1 117.6(4) . . ?
N2 C11 C10 122.4(5) . . ?
N2 C11 C12 121.1(5) . . ?
C10 C11 C12 116.6(5) . . ?
C8 C9 C10 122.8(5) . . ?
C13 C12 C11 122.6(5) . . ?
C9 C8 C13 117.7(5) . . ?
C9 C8 N1 116.5(5) . . ?
C13 C8 N1 125.8(5) . . ?
N1 C7 C6 119.7(5) . . ?
C12 C13 C8 120.2(5) . . ?
C9 C10 C11 120.2(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.84 2.561(5) 146.0 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_151010e
_database_code_depnum_ccdc_archive 'CCDC 1434487'
_audit_update_record             
;
2015-10-31 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32

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

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                   14.9189(13)
_cell_length_b                   5.9680(5)
_cell_length_c                   20.9971(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.968(3)
_cell_angle_gamma                90.00
_cell_volume                     1411.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1632
_cell_measurement_theta_min      2.738
_cell_measurement_theta_max      26.981

_exptl_crystal_description       Prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_process_details   sadabs

_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  '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            6735
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2472
_reflns_number_gt                1448
_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)+(0.0458P)²+0.4608P] 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         2472
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.24352(15) 0.5360(3) 0.23882(11) 0.0432(5) Uani 1 1 d . . .
N2 N 0.08051(17) 0.4410(3) 0.41459(13) 0.0540(5) Uani 1 1 d . . .
O1 O 0.24081(14) 0.7983(2) 0.13946(10) 0.0600(5) Uani 1 1 d . . .
H1 H 0.2236 0.7528 0.1671 0.090 Uiso 1 1 calc R . .
O2 O 0.46038(14) 0.5651(3) 0.05883(10) 0.0550(5) Uani 1 1 d . . .
C1 C 0.30198(18) 0.3931(4) 0.23271(13) 0.0415(5) Uani 1 1 d . . .
H1A H 0.3220 0.2560 0.2601 0.050 Uiso 1 1 calc R . .
C2 C 0.33733(17) 0.4395(3) 0.18454(13) 0.0378(5) Uani 1 1 d . . .
C3 C 0.30658(18) 0.6433(3) 0.13990(13) 0.0403(5) Uani 1 1 d . . .
C4 C 0.34514(18) 0.6882(3) 0.09633(14) 0.0419(6) Uani 1 1 d . . .
H4 H 0.3236 0.8212 0.0663 0.050 Uiso 1 1 calc R . .
C5 C 0.41541(18) 0.5347(3) 0.09780(13) 0.0389(5) Uani 1 1 d . . .
C6 C 0.44653(19) 0.3331(4) 0.14098(14) 0.0462(6) Uani 1 1 d . . .
H6 H 0.4939 0.2302 0.1415 0.055 Uiso 1 1 calc R . .
C7 C 0.40668(18) 0.2878(3) 0.18266(13) 0.0430(6) Uani 1 1 d . . .
H7 H 0.4265 0.1515 0.2106 0.052 Uiso 1 1 calc R . .
C8 C 0.4306(2) 0.7643(4) 0.01141(17) 0.0643(7) Uani 1 1 d . . .
H8A H 0.3459 0.7760 -0.0315 0.096 Uiso 1 1 calc R . .
H8B H 0.4649 0.7595 -0.0144 0.096 Uiso 1 1 calc R . .
H8C H 0.4609 0.8918 0.0482 0.096 Uiso 1 1 calc R . .
C9 C 0.20878(17) 0.5004(3) 0.28661(13) 0.0390(5) Uani 1 1 d . . .
C10 C 0.13948(19) 0.6647(4) 0.28202(14) 0.0465(6) Uani 1 1 d . . .
H10 H 0.1205 0.7912 0.2494 0.056 Uiso 1 1 calc R . .
C11 C 0.09739(19) 0.6486(4) 0.32377(14) 0.0465(6) Uani 1 1 d . . .
H11 H 0.0508 0.7632 0.3186 0.056 Uiso 1 1 calc R . .
C12 C 0.12381(18) 0.4619(4) 0.37390(13) 0.0400(5) Uani 1 1 d . . .
C13 C 0.19677(18) 0.2969(4) 0.38038(14) 0.0457(6) Uani 1 1 d . . .
H13 H 0.2182 0.1723 0.4144 0.055 Uiso 1 1 calc R . .
C14 C 0.23729(19) 0.3154(4) 0.33746(14) 0.0463(6) Uani 1 1 d . . .
H14 H 0.2845 0.2023 0.3426 0.056 Uiso 1 1 calc R . .
C15 C 0.0063(2) 0.6111(4) 0.40783(17) 0.0660(8) Uani 1 1 d . . .
H15A H 0.0539 0.7389 0.4409 0.099 Uiso 1 1 calc R . .
H15B H -0.0309 0.5530 0.4282 0.099 Uiso 1 1 calc R . .
H15C H -0.0536 0.6548 0.3499 0.099 Uiso 1 1 calc R . .
C16 C 0.1031(2) 0.2469(4) 0.46331(18) 0.0721(8) Uani 1 1 d . . .
H16A H 0.0730 0.1164 0.4280 0.108 Uiso 1 1 calc R . .
H16B H 0.0643 0.2632 0.4857 0.108 Uiso 1 1 calc R . .
H16C H 0.1870 0.2312 0.5089 0.108 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
N1 0.0410(10) 0.0473(11) 0.0464(12) -0.0010(9) 0.0308(10) -0.0017(9)
N2 0.0708(14) 0.0526(12) 0.0598(14) 0.0113(10) 0.0520(12) 0.0120(10)
O1 0.0726(11) 0.0530(10) 0.0827(13) 0.0183(9) 0.0632(11) 0.0212(9)
O2 0.0686(11) 0.0540(10) 0.0664(12) 0.0120(9) 0.0547(10) 0.0127(8)
C1 0.0399(12) 0.0408(12) 0.0381(13) 0.0005(11) 0.0231(11) -0.0047(10)
C2 0.0368(12) 0.0382(12) 0.0359(13) -0.0035(10) 0.0227(11) -0.0044(10)
C3 0.0380(12) 0.0395(12) 0.0428(14) -0.0003(11) 0.0262(11) 0.0038(10)
C4 0.0455(13) 0.0375(12) 0.0469(14) 0.0086(11) 0.0321(12) 0.0064(10)
C5 0.0409(12) 0.0397(12) 0.0392(13) -0.0009(10) 0.0276(11) 0.0002(10)
C6 0.0521(14) 0.0399(12) 0.0531(15) 0.0022(11) 0.0374(13) 0.0084(10)
C7 0.0480(13) 0.0359(12) 0.0432(14) 0.0023(11) 0.0290(12) 0.0031(10)
C8 0.0792(18) 0.0620(16) 0.0768(19) 0.0190(15) 0.0621(17) 0.0135(14)
C9 0.0352(12) 0.0417(12) 0.0382(13) -0.0002(10) 0.0232(11) -0.0033(10)
C10 0.0484(13) 0.0437(13) 0.0493(15) 0.0104(11) 0.0329(13) 0.0068(11)
C11 0.0472(13) 0.0463(13) 0.0508(15) 0.0056(11) 0.0342(12) 0.0072(11)
C12 0.0380(12) 0.0441(12) 0.0349(13) -0.0026(10) 0.0226(11) -0.0044(10)
C13 0.0492(13) 0.0414(12) 0.0476(15) 0.0098(11) 0.0322(13) 0.0048(11)
C14 0.0443(13) 0.0447(13) 0.0523(15) 0.0008(12) 0.0327(13) 0.0043(10)
C15 0.0896(19) 0.0603(16) 0.080(2) 0.0060(15) 0.0693(18) 0.0093(15)
C16 0.0844(19) 0.0738(18) 0.083(2) 0.0276(16) 0.0658(18) 0.0188(15)

_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 1.285(3) . ?
N1 C9 1.415(3) . ?
N2 C12 1.373(3) . ?
N2 C16 1.432(3) . ?
N2 C15 1.439(3) . ?
O1 C3 1.344(2) . ?
O1 H1 0.8200 . ?
O2 C5 1.368(2) . ?
O2 C8 1.422(3) . ?
C1 C2 1.441(3) . ?
C1 H1A 0.9300 . ?
C2 C7 1.395(3) . ?
C2 C3 1.416(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.369(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.382(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 C9 123.99(19) . . ?
C12 N2 C16 122.11(19) . . ?
C12 N2 C15 121.35(19) . . ?
C16 N2 C15 116.51(19) . . ?
C3 O1 H1 109.5 . . ?
C5 O2 C8 118.64(17) . . ?
N1 C1 C2 121.8(2) . . ?
N1 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C7 C2 C3 117.61(19) . . ?
C7 C2 C1 120.98(19) . . ?
C3 C2 C1 121.37(19) . . ?
O1 C3 C4 118.59(19) . . ?
O1 C3 C2 120.94(19) . . ?
C4 C3 C2 120.47(19) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O2 C5 C4 124.24(19) . . ?
O2 C5 C6 114.82(18) . . ?
C4 C5 C6 120.94(19) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 122.1(2) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.0(2) . . ?
C10 C9 N1 116.7(2) . . ?
C14 C9 N1 126.3(2) . . ?
C11 C10 C9 122.6(2) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
N2 C12 C11 121.6(2) . . ?
N2 C12 C13 121.8(2) . . ?
C11 C12 C13 116.63(19) . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C9 N1 C1 C2 -178.72(18) . . . . ?
N1 C1 C2 C7 176.2(2) . . . . ?
N1 C1 C2 C3 -1.6(3) . . . . ?
C7 C2 C3 O1 -179.45(18) . . . . ?
C1 C2 C3 O1 -1.6(3) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 177.68(19) . . . . ?
O1 C3 C4 C5 178.19(19) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C8 O2 C5 C4 -2.0(3) . . . . ?
C8 O2 C5 C6 178.4(2) . . . . ?
C3 C4 C5 O2 -178.3(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
O2 C5 C6 C7 179.46(19) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C3 C2 C7 C6 1.3(3) . . . . ?
C1 C2 C7 C6 -176.5(2) . . . . ?
C1 N1 C9 C10 -175.8(2) . . . . ?
C1 N1 C9 C14 3.9(3) . . . . ?
C14 C9 C10 C11 -1.3(3) . . . . ?
N1 C9 C10 C11 178.5(2) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C16 N2 C12 C11 177.5(2) . . . . ?
C15 N2 C12 C11 -0.3(3) . . . . ?
C16 N2 C12 C13 -2.4(3) . . . . ?
C15 N2 C12 C13 179.8(2) . . . . ?
C10 C11 C12 N2 -178.7(2) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
N2 C12 C13 C14 178.1(2) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
N1 C9 C14 C13 -179.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_www
_database_code_depnum_ccdc_archive 'CCDC 1434488'
_audit_update_record             
;
2015-10-31 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30

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   Pbca

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'
'-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                   11.278(2)
_cell_length_b                   8.2043(16)
_cell_length_c                   27.475(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2542.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.080
_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  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8605
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2169
_reflns_number_gt                1368
_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)+(0.0740P)²+0.2688P] 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         2169
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0940
_refine_ls_wR_factor_ref         0.2099
_refine_ls_wR_factor_gt          0.1812
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.196
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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 0.4007(3) 0.0862(4) 0.57415(11) 0.0524(9) Uani 1 1 d . . .
O1 O 0.5227(3) 0.0933(4) 0.65282(10) 0.0711(9) Uani 1 1 d D . .
C6 C 0.3447(4) -0.0636(5) 0.64475(13) 0.0489(10) Uani 1 1 d . . .
C11 C 0.3932(4) 0.2625(5) 0.42890(13) 0.0514(10) Uani 1 1 d . . .
C9 C 0.3096(4) 0.0846(5) 0.49128(14) 0.0559(11) Uani 1 1 d . . .
H9 H 0.2534 0.0071 0.5001 0.067 Uiso 1 1 calc R . .
C8 C 0.3930(3) 0.1376(5) 0.52518(12) 0.0472(10) Uani 1 1 d . . .
C13 C 0.4772(4) 0.2496(5) 0.51005(13) 0.0556(11) Uani 1 1 d . . .
H13 H 0.5348 0.2839 0.5320 0.067 Uiso 1 1 calc R . .
C2 C 0.4566(4) -0.0637(5) 0.71994(14) 0.0616(12) Uani 1 1 d . . .
H2 H 0.5217 -0.0294 0.7380 0.074 Uiso 1 1 calc R . .
C12 C 0.4782(4) 0.3122(5) 0.46313(13) 0.0562(11) Uani 1 1 d . . .
H12 H 0.5358 0.3878 0.4543 0.067 Uiso 1 1 calc R . .
C7 C 0.3291(4) -0.0143(5) 0.59445(13) 0.0524(11) Uani 1 1 d . . .
H7 H 0.2660 -0.0563 0.5766 0.063 Uiso 1 1 calc R . .
C1 C 0.4424(4) -0.0105(5) 0.67252(14) 0.0518(10) Uani 1 1 d . . .
N2 N 0.3928(3) 0.3251(5) 0.38260(11) 0.0689(11) Uani 1 1 d . . .
C10 C 0.3104(4) 0.1470(6) 0.44472(14) 0.0626(12) Uani 1 1 d . . .
H10 H 0.2533 0.1108 0.4228 0.075 Uiso 1 1 calc R . .
C3 C 0.3747(5) -0.1673(6) 0.74034(15) 0.0704(13) Uani 1 1 d . . .
H3 H 0.3853 -0.2031 0.7722 0.084 Uiso 1 1 calc R . .
C5 C 0.2637(4) -0.1664(6) 0.66703(15) 0.0632(12) Uani 1 1 d . . .
H5 H 0.1979 -0.2010 0.6494 0.076 Uiso 1 1 calc R . .
C4 C 0.2767(4) -0.2193(6) 0.71420(15) 0.0700(14) Uani 1 1 d . . .
H4 H 0.2210 -0.2883 0.7283 0.084 Uiso 1 1 calc R . .
C15 C 0.4807(4) 0.4424(6) 0.36712(15) 0.0751(15) Uani 1 1 d . . .
H15A H 0.4749 0.5384 0.3869 0.113 Uiso 1 1 calc R . .
H15B H 0.4671 0.4707 0.3337 0.113 Uiso 1 1 calc R . .
H15C H 0.5584 0.3959 0.3704 0.113 Uiso 1 1 calc R . .
C14 C 0.3048(4) 0.2712(7) 0.34764(14) 0.0796(16) Uani 1 1 d . . .
H14A H 0.3251 0.1643 0.3362 0.119 Uiso 1 1 calc R . .
H14B H 0.3028 0.3456 0.3207 0.119 Uiso 1 1 calc R . .
H14C H 0.2283 0.2681 0.3629 0.119 Uiso 1 1 calc R . .
H1 H 0.5054 0.1651 0.6226 0.35(6) Uiso 1 1 calc RD . .

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 0.055(2) 0.050(2) 0.052(2) -0.0038(15) 0.0039(15) 0.0033(18)
O1 0.061(2) 0.076(2) 0.0769(19) 0.0120(16) -0.0058(14) -0.0211(17)
C6 0.056(3) 0.043(2) 0.048(2) -0.0042(17) 0.0061(19) 0.000(2)
C11 0.048(3) 0.054(3) 0.051(2) -0.0059(19) 0.0043(18) 0.009(2)
C9 0.054(3) 0.059(3) 0.055(3) 0.000(2) -0.0006(19) -0.009(2)
C8 0.048(2) 0.044(2) 0.049(2) -0.0072(18) -0.0004(17) 0.0019(19)
C13 0.058(3) 0.052(3) 0.057(3) -0.0083(19) -0.0092(18) -0.006(2)
C2 0.069(3) 0.067(3) 0.049(3) 0.001(2) -0.001(2) 0.002(2)
C12 0.063(3) 0.057(3) 0.049(3) 0.0018(19) -0.0002(18) -0.007(2)
C7 0.051(3) 0.050(3) 0.057(3) -0.0043(19) -0.0020(18) -0.002(2)
C1 0.055(3) 0.044(3) 0.057(2) -0.0038(19) -0.0002(19) 0.004(2)
N2 0.071(3) 0.086(3) 0.050(2) 0.0054(19) -0.0063(17) -0.006(2)
C10 0.050(3) 0.082(4) 0.056(3) -0.008(2) -0.0034(19) -0.005(2)
C3 0.095(4) 0.064(3) 0.052(3) 0.004(2) 0.007(2) 0.000(3)
C5 0.065(3) 0.059(3) 0.066(3) -0.003(2) -0.002(2) -0.012(2)
C4 0.086(4) 0.062(3) 0.062(3) 0.003(2) 0.009(2) -0.015(3)
C15 0.085(4) 0.080(4) 0.061(3) 0.008(2) 0.009(2) 0.001(3)
C14 0.069(3) 0.113(5) 0.057(3) 0.001(3) -0.014(2) 0.013(3)

_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 C7 1.282(5) . ?
N1 C8 1.413(5) . ?
O1 C1 1.356(5) . ?
C6 C5 1.386(5) . ?
C6 C1 1.409(5) . ?
C6 C7 1.451(5) . ?
C11 N2 1.372(5) . ?
C11 C10 1.400(6) . ?
C11 C12 1.404(5) . ?
C9 C10 1.378(5) . ?
C9 C8 1.393(5) . ?
C8 C13 1.385(5) . ?
C13 C12 1.388(5) . ?
C2 C3 1.375(6) . ?
C2 C1 1.383(5) . ?
N2 C15 1.445(6) . ?
N2 C14 1.450(5) . ?
C3 C4 1.386(6) . ?
C5 C4 1.375(6) . ?

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
C7 N1 C8 124.6(4) . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C7 120.7(4) . . ?
C1 C6 C7 121.7(4) . . ?
N2 C11 C10 122.6(4) . . ?
N2 C11 C12 121.0(4) . . ?
C10 C11 C12 116.4(4) . . ?
C10 C9 C8 120.0(4) . . ?
C13 C8 C9 118.0(4) . . ?
C13 C8 N1 116.2(3) . . ?
C9 C8 N1 125.8(4) . . ?
C12 C13 C8 122.0(4) . . ?
C3 C2 C1 120.1(4) . . ?
C13 C12 C11 120.6(4) . . ?
N1 C7 C6 121.1(4) . . ?
O1 C1 C2 119.8(4) . . ?
O1 C1 C6 120.0(3) . . ?
C2 C1 C6 120.2(4) . . ?
C11 N2 C15 121.3(4) . . ?
C11 N2 C14 120.2(4) . . ?
C15 N2 C14 118.5(3) . . ?
C9 C10 C11 122.9(4) . . ?
C2 C3 C4 121.0(4) . . ?
C4 C5 C6 122.5(4) . . ?
C5 C4 C3 118.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 1.04 1.89 2.563(4) 119.1 .

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.919
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
