# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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   P21/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                   15.852(5)
_cell_length_b                   6.0728(13)
_cell_length_c                   17.750(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.655(9)
_cell_angle_gamma                90.00
_cell_volume                     1553.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      5.050
_cell_measurement_theta_max      48.268

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11739
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         28.09
_reflns_number_total             3736
_reflns_number_gt                2456
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0945P)²+0.0588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3736
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_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 0.60720(12) 0.5698(3) 1.00759(11) 0.0766(6) Uani 1 1 d . . .
O2 O 0.88158(10) 0.0049(2) 1.00926(9) 0.0508(4) Uani 1 1 d . . .
H2 H 0.8906 -0.0894 1.0449 0.076 Uiso 1 1 calc R . .
N1 N 1.05262(10) 0.3268(2) 0.87080(9) 0.0348(4) Uani 1 1 d . . .
C1 C 0.56611(17) 0.7286(4) 0.94589(15) 0.0634(6) Uani 1 1 d . . .
H1A H 0.6118 0.8360 0.9487 0.095 Uiso 1 1 calc R . .
H1B H 0.5166 0.7997 0.9542 0.095 Uiso 1 1 calc R . .
H1C H 0.5418 0.6590 0.8925 0.095 Uiso 1 1 calc R . .
C2 C 0.67628(13) 0.4383(3) 1.00453(12) 0.0450(5) Uani 1 1 d . . .
C3 C 0.72722(12) 0.4818(3) 0.95978(11) 0.0376(4) Uani 1 1 d . . .
H3 H 0.7141 0.6082 0.9273 0.045 Uiso 1 1 calc R . .
C4 C 0.79873(12) 0.3412(3) 0.96140(10) 0.0317(4) Uani 1 1 d . . .
C5 C 0.84872(12) 0.4056(3) 0.91210(11) 0.0354(4) Uani 1 1 d . . .
H5 H 0.8213 0.5183 0.8742 0.042 Uiso 1 1 calc R . .
C6 C 0.92817(12) 0.3271(3) 0.91312(10) 0.0325(4) Uani 1 1 d . . .
H6 H 0.9576 0.2142 0.9503 0.039 Uiso 1 1 calc R . .
C7 C 0.97184(12) 0.4047(2) 0.86070(10) 0.0304(4) Uani 1 1 d . . .
C8 C 1.07714(12) 0.4270(2) 0.81011(10) 0.0338(4) Uani 1 1 d . . .
C9 C 1.15786(14) 0.3987(3) 0.79876(13) 0.0467(5) Uani 1 1 d . . .
H9 H 1.2044 0.3040 0.8326 0.056 Uiso 1 1 calc R . .
C10 C 1.16737(16) 0.5154(3) 0.73551(13) 0.0531(5) Uani 1 1 d . . .
H10 H 1.2211 0.4990 0.7270 0.064 Uiso 1 1 calc R . .
C11 C 0.69635(15) 0.2508(3) 1.05358(13) 0.0551(6) Uani 1 1 d . . .
H11 H 0.6633 0.2205 1.0851 0.066 Uiso 1 1 calc R . .
C12 C 0.76518(15) 0.1098(3) 1.05559(13) 0.0524(5) Uani 1 1 d . . .
H12 H 0.7778 -0.0155 1.0886 0.063 Uiso 1 1 calc R . .
C13 C 0.81635(12) 0.1490(3) 1.00988(10) 0.0358(4) Uani 1 1 d . . .
C14 C 1.00763(13) 0.5685(3) 0.75963(10) 0.0368(4) Uani 1 1 d . . .
C15 C 1.01800(15) 0.6827(3) 0.69635(12) 0.0526(5) Uani 1 1 d . . .
H15 H 0.9715 0.7763 0.6619 0.063 Uiso 1 1 calc R . .
C16 C 1.09860(17) 0.6550(3) 0.68524(13) 0.0567(6) Uani 1 1 d . . .
H16 H 1.1064 0.7318 0.6433 0.068 Uiso 1 1 calc R . .
C17 C 0.93078(12) 0.5682(3) 0.78854(10) 0.0343(4) Uani 1 1 d . . .
C18 C 0.84039(14) 0.4784(4) 0.72078(12) 0.0544(5) Uani 1 1 d . . .
H18A H 0.8235 0.5655 0.6715 0.082 Uiso 1 1 calc R . .
H18B H 0.7918 0.4855 0.7396 0.082 Uiso 1 1 calc R . .
H18C H 0.8494 0.3283 0.7089 0.082 Uiso 1 1 calc R . .
C19 C 0.91800(16) 0.8019(3) 0.81611(14) 0.0543(6) Uani 1 1 d . . .
H19A H 0.9754 0.8511 0.8593 0.081 Uiso 1 1 calc R . .
H19B H 0.8706 0.7996 0.8365 0.081 Uiso 1 1 calc R . .
H19C H 0.9000 0.9005 0.7697 0.081 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 1.375(2) . ?
O1 C1 1.400(3) . ?
O2 C13 1.358(2) . ?
O2 H2 0.8200 . ?
N1 C7 1.305(2) . ?
N1 C8 1.425(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.374(2) . ?
C2 C11 1.387(3) . ?
C3 C4 1.410(2) . ?
C3 H3 0.9300 . ?
C4 C13 1.407(2) . ?
C4 C5 1.458(2) . ?
C5 C6 1.340(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(2) . ?
C6 H6 0.9300 . ?
C7 C17 1.535(2) . ?
C8 C9 1.387(2) . ?
C8 C14 1.390(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C16 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.387(2) . ?
C14 C17 1.506(2) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.536(3) . ?
C17 C19 1.542(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 119.19(16) . . ?
C13 O2 H2 109.5 . . ?
C7 N1 C8 107.64(13) . . ?
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 C3 125.54(17) . . ?
O1 C2 C11 115.45(17) . . ?
C3 C2 C11 118.97(16) . . ?
C2 C3 C4 122.23(15) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C13 C4 C3 117.87(15) . . ?
C13 C4 C5 124.82(15) . . ?
C3 C4 C5 117.31(14) . . ?
C6 C5 C4 129.75(16) . . ?
C6 C5 H5 115.1 . . ?
C4 C5 H5 115.1 . . ?
C5 C6 C7 124.96(15) . . ?
C5 C6 H6 117.5 . . ?
C7 C6 H6 117.5 . . ?
N1 C7 C6 119.83(15) . . ?
N1 C7 C17 113.53(14) . . ?
C6 C7 C17 126.58(15) . . ?
C9 C8 C14 120.95(16) . . ?
C9 C8 N1 128.05(16) . . ?
C14 C8 N1 111.00(15) . . ?
C8 C9 C10 118.19(18) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C16 C10 C9 121.03(19) . . ?
C16 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C2 119.92(17) . . ?
C12 C11 H11 120.0 . . ?
C2 C11 H11 120.0 . . ?
C11 C12 C13 121.96(17) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O2 C13 C12 121.82(15) . . ?
O2 C13 C4 119.14(15) . . ?
C12 C13 C4 119.02(16) . . ?
C15 C14 C8 120.10(17) . . ?
C15 C14 C17 131.49(17) . . ?
C8 C14 C17 108.41(14) . . ?
C16 C15 C14 118.94(19) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C10 C16 C15 120.80(18) . . ?
C10 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C14 C17 C7 99.41(13) . . ?
C14 C17 C18 110.90(15) . . ?
C7 C17 C18 110.87(14) . . ?
C14 C17 C19 109.81(14) . . ?
C7 C17 C19 113.38(15) . . ?
C18 C17 C19 111.84(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.09
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 1025091'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33

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   P21/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                   16.299(2)
_cell_length_b                   5.7664(6)
_cell_length_c                   16.537(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.692(5)
_cell_angle_gamma                90.00
_cell_volume                     1552.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3333
_cell_measurement_theta_min      4.932
_cell_measurement_theta_max      55.120

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11865
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.08
_reflns_number_total             3752
_reflns_number_gt                2431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0884P)²+0.0896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3752
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.82679(11) 0.1196(3) -0.03778(10) 0.0772(5) Uani 1 1 d . . .
O2 O 0.94187(10) 0.2813(3) -0.00469(9) 0.0590(4) Uani 1 1 d . . .
O3 O 0.70825(8) 0.8934(2) 0.19230(8) 0.0483(4) Uani 1 1 d . . .
H3 H 0.6614 0.8505 0.2003 0.072 Uiso 1 1 calc R . .
N1 N 0.86722(11) 0.2674(3) -0.00104(8) 0.0438(4) Uani 1 1 d . . .
N2 N 0.94991(9) 1.3149(2) 0.27926(8) 0.0388(4) Uani 1 1 d . . .
C1 C 1.13965(14) 1.6151(3) 0.41835(11) 0.0543(5) Uani 1 1 d . . .
H1 H 1.1835 1.6720 0.4505 0.065 Uiso 1 1 calc R . .
C2 C 1.15457(12) 1.4672(3) 0.35465(10) 0.0434(4) Uani 1 1 d . . .
H2 H 1.2079 1.4264 0.3430 0.052 Uiso 1 1 calc R . .
C3 C 1.08837(11) 1.3818(3) 0.30898(9) 0.0335(4) Uani 1 1 d . . .
C4 C 1.08232(10) 1.2218(3) 0.23642(9) 0.0316(4) Uani 1 1 d . . .
C5 C 0.98999(10) 1.1853(3) 0.22972(9) 0.0328(4) Uani 1 1 d . . .
C6 C 0.95113(11) 1.0149(3) 0.17595(10) 0.0380(4) Uani 1 1 d . . .
H6 H 0.9824 0.9467 0.1368 0.046 Uiso 1 1 calc R . .
C7 C 0.87305(11) 0.9513(3) 0.17984(10) 0.0389(4) Uani 1 1 d . . .
H7 H 0.8421 1.0353 0.2155 0.047 Uiso 1 1 calc R . .
C8 C 0.82989(10) 0.7665(3) 0.13536(9) 0.0339(4) Uani 1 1 d . . .
C9 C 0.86899(11) 0.6088(3) 0.08623(9) 0.0361(4) Uani 1 1 d . . .
H9 H 0.9249 0.6235 0.0784 0.043 Uiso 1 1 calc R . .
C10 C 0.82494(11) 0.4314(3) 0.04922(9) 0.0354(4) Uani 1 1 d . . .
C11 C 0.74137(12) 0.4026(3) 0.05937(10) 0.0420(4) Uani 1 1 d . . .
H11 H 0.7128 0.2809 0.0341 0.050 Uiso 1 1 calc R . .
C12 C 0.70167(11) 0.5570(3) 0.10741(10) 0.0418(4) Uani 1 1 d . . .
H12 H 0.6458 0.5399 0.1146 0.050 Uiso 1 1 calc R . .
C13 C 0.74451(10) 0.7389(3) 0.14531(9) 0.0350(4) Uani 1 1 d . . .
C14 C 1.00874(11) 1.4390(3) 0.32800(10) 0.0361(4) Uani 1 1 d . . .
C15 C 1.06075(16) 1.6788(4) 0.43467(11) 0.0592(6) Uani 1 1 d . . .
H15 H 1.0523 1.7827 0.4765 0.071 Uiso 1 1 calc R . .
C16 C 0.99345(14) 1.5913(3) 0.38997(11) 0.0531(5) Uani 1 1 d . . .
H16 H 0.9401 1.6336 0.4013 0.064 Uiso 1 1 calc R . .
C17 C 1.10994(12) 1.3450(3) 0.15965(10) 0.0464(5) Uani 1 1 d . . .
H17A H 1.0800 1.4874 0.1522 0.070 Uiso 1 1 calc R . .
H17B H 1.0994 1.2465 0.1135 0.070 Uiso 1 1 calc R . .
H17C H 1.1677 1.3779 0.1653 0.070 Uiso 1 1 calc R . .
C18 C 1.12993(13) 0.9954(3) 0.24930(13) 0.0515(5) Uani 1 1 d . . .
H18A H 1.1866 1.0296 0.2627 0.077 Uiso 1 1 calc R . .
H18B H 1.1259 0.9048 0.2006 0.077 Uiso 1 1 calc R . .
H18C H 1.1072 0.9097 0.2927 0.077 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 N1 1.222(2) . ?
O2 N1 1.224(2) . ?
O3 C13 1.338(2) . ?
O3 H3 0.8200 . ?
N1 C10 1.454(2) . ?
N2 C5 1.307(2) . ?
N2 C14 1.417(2) . ?
C1 C15 1.376(3) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C14 1.389(2) . ?
C3 C4 1.513(2) . ?
C4 C5 1.519(2) . ?
C4 C18 1.529(2) . ?
C4 C17 1.540(2) . ?
C5 C6 1.451(2) . ?
C6 C7 1.329(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.457(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(2) . ?
C8 C13 1.418(2) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(2) . ?
C11 C12 1.375(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9300 . ?
C14 C16 1.381(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C13 O3 H3 109.5 . . ?
O1 N1 O2 122.36(16) . . ?
O1 N1 C10 118.63(17) . . ?
O2 N1 C10 119.01(15) . . ?
C5 N2 C14 107.49(14) . . ?
C15 C1 C2 120.82(19) . . ?
C15 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.38(18) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C14 120.46(16) . . ?
C2 C3 C4 132.24(16) . . ?
C14 C3 C4 107.30(14) . . ?
C3 C4 C5 99.78(12) . . ?
C3 C4 C18 113.37(14) . . ?
C5 C4 C18 112.73(14) . . ?
C3 C4 C17 111.21(13) . . ?
C5 C4 C17 109.32(14) . . ?
C18 C4 C17 110.03(14) . . ?
N2 C5 C6 123.72(15) . . ?
N2 C5 C4 113.45(14) . . ?
C6 C5 C4 122.77(14) . . ?
C7 C6 C5 123.27(16) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C6 C7 C8 128.17(16) . . ?
C6 C7 H7 115.9 . . ?
C8 C7 H7 115.9 . . ?
C9 C8 C13 118.21(15) . . ?
C9 C8 C7 123.26(16) . . ?
C13 C8 C7 118.47(15) . . ?
C10 C9 C8 120.05(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.91(16) . . ?
C9 C10 N1 119.09(16) . . ?
C11 C10 N1 118.99(15) . . ?
C12 C11 C10 118.86(16) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.53(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O3 C13 C12 122.48(16) . . ?
O3 C13 C8 117.09(15) . . ?
C12 C13 C8 120.43(16) . . ?
C16 C14 C3 121.45(17) . . ?
C16 C14 N2 127.02(17) . . ?
C3 C14 N2 111.47(14) . . ?
C1 C15 C16 121.36(18) . . ?
C1 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C14 C16 C15 117.43(19) . . ?
C14 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.08
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 1025092'
