# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2011acc0752
_database_code_CSD               11AC0752


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'N-[2-(4-nitrophenyl)-3-(phenylamino)allylidene]aniline '
_chemical_name_common            ?
_chemical_melting_point          453
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38

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/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                   8.649(7)
_cell_length_b                   21.553(15)
_cell_length_c                   9.886(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.782(9)
_cell_angle_gamma                90.00
_cell_volume                     1734(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4391
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      31.1

_exptl_crystal_description       Slab
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9905
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         RA
_diffrn_radiation_monochromator  'Varimax mirror'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6840
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3031
_reflns_number_gt                2330
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0296P)²+0.7328P] 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         3031
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003

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 -0.3695(3) 1.02755(11) 0.7303(3) 0.0469(7) Uani 1 1 d . . .
O2 O -0.3275(3) 1.06743(11) 0.5443(3) 0.0516(8) Uani 1 1 d . . .
N1 N -0.3190(3) 1.02376(14) 0.6282(3) 0.0359(8) Uani 1 1 d . . .
N2 N -0.0587(3) 0.68242(12) 0.5445(3) 0.0269(7) Uani 1 1 d . . .
N3 N 0.1379(3) 0.73973(14) 0.4287(3) 0.0282(7) Uani 1 1 d . . .
H93 H 0.094(4) 0.7032(16) 0.459(4) 0.056(12) Uiso 1 1 d . . .
C1 C -0.2460(4) 0.96546(15) 0.6039(4) 0.0289(8) Uani 1 1 d . . .
C2 C -0.2323(4) 0.91618(15) 0.6984(3) 0.0278(8) Uani 1 1 d . . .
H2 H -0.2694 0.9201 0.7781 0.033 Uiso 1 1 calc R . .
C3 C -0.1633(4) 0.86135(15) 0.6734(3) 0.0288(8) Uani 1 1 d . . .
H3 H -0.1514 0.8278 0.7383 0.035 Uiso 1 1 calc R . .
C4 C -0.1099(4) 0.85379(15) 0.5541(3) 0.0258(8) Uani 1 1 d . . .
C5 C -0.1243(4) 0.90564(15) 0.4639(3) 0.0309(8) Uani 1 1 d . . .
H5 H -0.0871 0.9024 0.3841 0.037 Uiso 1 1 calc R . .
C6 C -0.1908(4) 0.96103(16) 0.4877(4) 0.0345(9) Uani 1 1 d . . .
H6 H -0.1986 0.9955 0.4258 0.041 Uiso 1 1 calc R . .
C7 C -0.0455(4) 0.79369(15) 0.5243(3) 0.0254(8) Uani 1 1 d . . .
C8 C -0.1064(4) 0.73785(15) 0.5652(3) 0.0263(8) Uani 1 1 d . . .
H8 H -0.1870 0.7413 0.6104 0.032 Uiso 1 1 calc R . .
C9 C -0.1396(4) 0.62901(15) 0.5748(3) 0.0266(8) Uani 1 1 d . . .
C10 C -0.3035(4) 0.62957(15) 0.5700(3) 0.0268(8) Uani 1 1 d . . .
H10 H -0.3651 0.6670 0.5488 0.032 Uiso 1 1 calc R . .
C11 C -0.3758(4) 0.57525(15) 0.5964(3) 0.0300(8) Uani 1 1 d . . .
H11 H -0.4861 0.5760 0.5953 0.036 Uiso 1 1 calc R . .
C12 C -0.2878(4) 0.51989(16) 0.6243(3) 0.0331(9) Uani 1 1 d . . .
H12 H -0.3380 0.4829 0.6411 0.040 Uiso 1 1 calc R . .
C13 C -0.1267(4) 0.51909(16) 0.6273(3) 0.0312(8) Uani 1 1 d . . .
H13 H -0.0665 0.4813 0.6461 0.037 Uiso 1 1 calc R . .
C14 C -0.0526(4) 0.57293(15) 0.6031(3) 0.0303(8) Uani 1 1 d . . .
H14 H 0.0582 0.5718 0.6058 0.036 Uiso 1 1 calc R . .
C15 C 0.0728(4) 0.79211(16) 0.4586(3) 0.0284(8) Uani 1 1 d . . .
H15 H 0.1098 0.8305 0.4333 0.034 Uiso 1 1 calc R . .
C16 C 0.2614(4) 0.73427(16) 0.3651(3) 0.0285(8) Uani 1 1 d . . .
C17 C 0.2883(4) 0.67550(17) 0.3181(3) 0.0319(8) Uani 1 1 d . . .
H17 H 0.2282 0.6408 0.3328 0.038 Uiso 1 1 calc R . .
C18 C 0.4037(4) 0.66816(19) 0.2497(4) 0.0388(9) Uani 1 1 d . . .
H18 H 0.4216 0.6282 0.2170 0.047 Uiso 1 1 calc R . .
C19 C 0.4920(4) 0.71813(18) 0.2289(4) 0.0408(10) Uani 1 1 d . . .
H19 H 0.5690 0.7129 0.1804 0.049 Uiso 1 1 calc R . .
C20 C 0.4680(4) 0.77619(18) 0.2790(4) 0.0398(10) Uani 1 1 d . . .
H20 H 0.5315 0.8104 0.2673 0.048 Uiso 1 1 calc R . .
C21 C 0.3524(4) 0.78486(17) 0.3461(4) 0.0350(9) Uani 1 1 d . . .
H21 H 0.3353 0.8249 0.3788 0.042 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.231(3) . ?
O2 N1 1.240(3) . ?
N1 C1 1.462(4) . ?
N2 C8 1.302(4) . ?
N2 C9 1.431(4) . ?
N3 C15 1.339(4) . ?
N3 C16 1.416(4) . ?
C1 C6 1.388(4) . ?
C1 C2 1.393(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.414(4) . ?
C4 C5 1.408(4) . ?
C4 C7 1.478(4) . ?
C5 C6 1.379(4) . ?
C7 C15 1.385(4) . ?
C7 C8 1.426(4) . ?
C9 C14 1.401(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.392(4) . ?
C12 C13 1.383(5) . ?
C13 C14 1.385(4) . ?
C16 C21 1.394(4) . ?
C16 C17 1.395(4) . ?
C17 C18 1.392(4) . ?
C18 C19 1.376(5) . ?
C19 C20 1.387(5) . ?
C20 C21 1.387(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 122.8(3) . . ?
O1 N1 C1 119.0(3) . . ?
O2 N1 C1 118.2(3) . . ?
C8 N2 C9 120.1(3) . . ?
C15 N3 C16 127.3(3) . . ?
C6 C1 C2 121.8(3) . . ?
C6 C1 N1 118.9(3) . . ?
C2 C1 N1 119.2(3) . . ?
C3 C2 C1 118.4(3) . . ?
C2 C3 C4 122.0(3) . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C7 121.9(3) . . ?
C3 C4 C7 121.2(3) . . ?
C6 C5 C4 122.1(3) . . ?
C5 C6 C1 118.7(3) . . ?
C15 C7 C8 120.9(3) . . ?
C15 C7 C4 120.1(3) . . ?
C8 C7 C4 118.9(3) . . ?
N2 C8 C7 124.3(3) . . ?
C14 C9 C10 118.9(3) . . ?
C14 C9 N2 117.9(3) . . ?
C10 C9 N2 123.1(3) . . ?
C11 C10 C9 120.0(3) . . ?
C10 C11 C12 120.5(3) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 120.5(3) . . ?
C13 C14 C9 120.6(3) . . ?
N3 C15 C7 123.9(3) . . ?
C21 C16 C17 120.0(3) . . ?
C21 C16 N3 122.7(3) . . ?
C17 C16 N3 117.3(3) . . ?
C18 C17 C16 119.5(3) . . ?
C19 C18 C17 120.6(4) . . ?
C18 C19 C20 119.7(3) . . ?
C19 C20 C21 120.8(3) . . ?
C20 C21 C16 119.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046


#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag
#

_shelx_title                     ' 2011acc0752 in P2(1)/c'
_shelx_refln_list_code           4
_shelx_F_calc_maximum            113.48

_shelx_F_squared_multiplier      1.000



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_database_code_depnum_ccdc_archive 'CCDC 1000391'
#######################################################################
#
#                 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_2011acc0768
#PRF R13

_audit_creation_method           SHELXL-97


_chemical_compound_source        'Pedro Cintas'
_database_code_CSD               11AC0768
_database_code_depnum_ccdc_archive 'CCDC 1000392'

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29

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                   4.1847(19)
_cell_length_b                   13.013(6)
_cell_length_c                   24.919(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.169(8)
_cell_angle_gamma                90.00
_cell_volume                     1354.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3424
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      31.5

_exptl_crystal_description       Fragment
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6477
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2360
_reflns_number_gt                2016
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0492P)²+0.1248P] 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         2360
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.003
_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 0.0826(3) 0.90450(9) 0.03202(5) 0.0211(3) Uani 1 1 d . . .
O2 O -0.6036(4) 0.46598(10) 0.23832(6) 0.0355(4) Uani 1 1 d . . .
O3 O -0.7782(4) 0.58428(11) 0.29014(6) 0.0376(4) Uani 1 1 d . . .
N1 N -0.3207(4) 1.03866(11) 0.07523(6) 0.0176(4) Uani 1 1 d . . .
H901 H -0.176(5) 1.0263(16) 0.0478(9) 0.038(7) Uiso 1 1 d . . .
N2 N -0.6436(4) 0.55695(13) 0.24971(6) 0.0252(4) Uani 1 1 d . . .
C1 C -0.3623(5) 1.29531(14) 0.03221(8) 0.0217(5) Uani 1 1 d . . .
H1 H -0.4765 1.2758 -0.0002 0.026 Uiso 1 1 calc R . .
C2 C -0.2081(5) 1.38976(14) 0.03531(8) 0.0262(5) Uani 1 1 d . . .
H2 H -0.2196 1.4349 0.0053 0.031 Uiso 1 1 calc R . .
C3 C -0.0375(5) 1.41805(15) 0.08215(8) 0.0269(5) Uani 1 1 d . . .
H3 H 0.0716 1.4821 0.0841 0.032 Uiso 1 1 calc R . .
C4 C -0.0263(5) 1.35298(15) 0.12596(8) 0.0267(5) Uani 1 1 d . . .
H4 H 0.0889 1.3726 0.1583 0.032 Uiso 1 1 calc R . .
C5 C -0.1823(5) 1.25939(14) 0.12289(8) 0.0228(5) Uani 1 1 d . . .
H5 H -0.1740 1.2151 0.1532 0.027 Uiso 1 1 calc R . .
C6 C -0.3515(4) 1.22933(13) 0.07581(7) 0.0178(4) Uani 1 1 d . . .
C7 C -0.5295(5) 1.12858(13) 0.07282(8) 0.0197(4) Uani 1 1 d . . .
H7A H -0.6741 1.1252 0.1029 0.024 Uiso 1 1 calc R . .
H7B H -0.6639 1.1264 0.0389 0.024 Uiso 1 1 calc R . .
C8 C -0.3649(4) 0.96143(13) 0.10777(7) 0.0184(4) Uani 1 1 d . . .
H8 H -0.5139 0.9720 0.1346 0.022 Uiso 1 1 calc R . .
C9 C -0.2164(4) 0.86512(13) 0.10722(7) 0.0174(4) Uani 1 1 d . . .
C10 C 0.0018(4) 0.84347(14) 0.06707(7) 0.0184(4) Uani 1 1 d . . .
H10 H 0.0936 0.7767 0.0670 0.022 Uiso 1 1 calc R . .
C11 C -0.3133(4) 0.78562(14) 0.14500(7) 0.0176(4) Uani 1 1 d . . .
C12 C -0.4427(5) 0.81147(14) 0.19408(7) 0.0210(5) Uani 1 1 d . . .
H12 H -0.4528 0.8817 0.2042 0.025 Uiso 1 1 calc R . .
C13 C -0.5549(5) 0.73792(14) 0.22771(8) 0.0215(5) Uani 1 1 d . . .
H13 H -0.6509 0.7573 0.2599 0.026 Uiso 1 1 calc R . .
C14 C -0.5265(5) 0.63516(14) 0.21428(7) 0.0200(4) Uani 1 1 d . . .
C15 C -0.3937(5) 0.60558(14) 0.16725(8) 0.0219(5) Uani 1 1 d . . .
H15 H -0.3726 0.5348 0.1587 0.026 Uiso 1 1 calc R . .
C16 C -0.2919(5) 0.68024(14) 0.13280(8) 0.0207(5) Uani 1 1 d . . .
H16 H -0.2051 0.6601 0.1000 0.025 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.241(2) . ?
O2 N2 1.231(2) . ?
O3 N2 1.234(2) . ?
N1 C8 1.311(2) . ?
N1 C7 1.460(2) . ?
N2 C14 1.450(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.508(3) . ?
C8 C9 1.399(3) . ?
C9 C10 1.419(3) . ?
C9 C11 1.471(3) . ?
C11 C12 1.405(3) . ?
C11 C16 1.409(3) . ?
C12 C13 1.372(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.379(3) . ?
C15 C16 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 122.38(17) . . ?
O2 N2 O3 122.65(17) . . ?
O2 N2 C14 118.68(17) . . ?
O3 N2 C14 118.68(16) . . ?
C6 C1 C2 120.71(18) . . ?
C3 C2 C1 119.94(19) . . ?
C4 C3 C2 119.82(19) . . ?
C3 C4 C5 120.11(19) . . ?
C4 C5 C6 120.72(18) . . ?
C1 C6 C5 118.71(17) . . ?
C1 C6 C7 120.41(17) . . ?
C5 C6 C7 120.84(17) . . ?
N1 C7 C6 113.69(16) . . ?
N1 C8 C9 127.08(19) . . ?
C8 C9 C10 119.20(17) . . ?
C8 C9 C11 119.04(18) . . ?
C10 C9 C11 121.50(17) . . ?
O1 C10 C9 125.44(18) . . ?
C12 C11 C16 116.94(17) . . ?
C12 C11 C9 121.45(17) . . ?
C16 C11 C9 121.56(17) . . ?
C13 C12 C11 121.73(18) . . ?
C12 C13 C14 119.29(18) . . ?
C15 C14 C13 121.24(18) . . ?
C15 C14 N2 119.14(17) . . ?
C13 C14 N2 119.61(18) . . ?
C14 C15 C16 119.02(17) . . ?
C15 C16 C11 121.71(18) . . ?

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
N1 H901 O1 0.95(2) 1.97(2) 2.694(2) 131.1(18) .
N1 H901 O1 0.95(2) 2.24(2) 2.996(2) 136.1(18) 3_575

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045

