# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_mo_pt_dk_02_0m
_database_code_depnum_ccdc_archive 'CCDC 818213'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H23 N2 O3'
_chemical_formula_weight         399.45
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   P12(1)/c1
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                   13.853(7)
_cell_length_b                   9.965(5)
_cell_length_c                   15.005(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.891(10)
_cell_angle_gamma                90.00
_cell_volume                     2071.1(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14867
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         24.77
_reflns_number_total             3548
_reflns_number_gt                1798
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3548
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.033
_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 0.66536(13) 0.55287(18) 0.28704(12) 0.0558(6) Uani 1 1 d . . .
O2 O 0.65009(15) 0.7611(2) 0.22765(15) 0.0729(7) Uani 1 1 d . . .
O3 O 0.90027(14) 1.13610(19) -0.24648(12) 0.0549(5) Uani 1 1 d . . .
N1 N 0.77589(17) 0.6237(2) 0.19537(15) 0.0513(6) Uani 1 1 d . . .
H1 H 0.8055 0.5538 0.2154 0.062 Uiso 1 1 calc R . .
N2 N 0.81200(16) 1.0001(2) -0.00461(14) 0.0439(6) Uani 1 1 d . . .
C1 C 0.5707(2) 0.4158(3) 0.3764(2) 0.0788(11) Uani 1 1 d . . .
H1A H 0.5876 0.3470 0.3347 0.118 Uiso 1 1 calc R . .
H1B H 0.5078 0.3975 0.3996 0.118 Uiso 1 1 calc R . .
H1C H 0.6172 0.4175 0.4245 0.118 Uiso 1 1 calc R . .
C2 C 0.5696(2) 0.5501(3) 0.33005(19) 0.0529(8) Uani 1 1 d . . .
C3 C 0.6921(2) 0.6567(3) 0.23619(19) 0.0496(7) Uani 1 1 d . . .
C4 C 0.8192(2) 0.6910(3) 0.12430(18) 0.0450(7) Uani 1 1 d . . .
C5 C 0.79357(19) 0.8157(3) 0.09486(17) 0.0447(7) Uani 1 1 d . . .
H5 H 0.7448 0.8626 0.1232 0.054 Uiso 1 1 calc R . .
C6 C 0.84066(19) 0.8739(2) 0.02176(17) 0.0423(7) Uani 1 1 d . . .
C7 C 0.85609(19) 1.0560(3) -0.07321(17) 0.0416(7) Uani 1 1 d . . .
C8 C 0.82561(19) 1.1903(3) -0.10582(17) 0.0427(7) Uani 1 1 d . . .
C9 C 0.7700(2) 1.2854(3) -0.05624(18) 0.0451(7) Uani 1 1 d . . .
C10 C 0.7424(2) 1.2680(3) 0.03327(19) 0.0549(8) Uani 1 1 d . . .
H10 H 0.7635 1.1925 0.0643 0.066 Uiso 1 1 calc R . .
C11 C 0.6856(2) 1.3593(3) 0.0751(2) 0.0666(9) Uani 1 1 d . . .
H11 H 0.6686 1.3445 0.1340 0.080 Uiso 1 1 calc R . .
C12 C 0.6524(3) 1.4739(3) 0.0319(2) 0.0745(10) Uani 1 1 d . . .
H12 H 0.6124 1.5342 0.0608 0.089 Uiso 1 1 calc R . .
C13 C 0.4917(3) 0.5559(4) 0.2593(2) 0.0901(12) Uani 1 1 d . . .
H13A H 0.4953 0.6400 0.2284 0.135 Uiso 1 1 calc R . .
H13B H 0.4298 0.5476 0.2866 0.135 Uiso 1 1 calc R . .
H13C H 0.5004 0.4837 0.2178 0.135 Uiso 1 1 calc R . .
C14 C 0.8484(2) 1.2219(3) -0.19259(18) 0.0466(7) Uani 1 1 d . . .
C15 C 0.9736(2) 1.0638(3) -0.19720(19) 0.0579(8) Uani 1 1 d . . .
H15A H 1.0218 1.1263 -0.1746 0.069 Uiso 1 1 calc R . .
H15B H 1.0054 1.0010 -0.2364 0.069 Uiso 1 1 calc R . .
C16 C 0.93017(19) 0.9893(3) -0.12115(17) 0.0476(7) Uani 1 1 d . . .
C17 C 0.9574(2) 0.8640(3) -0.09542(19) 0.0570(8) Uani 1 1 d . . .
H17 H 1.0048 0.8187 -0.1267 0.068 Uiso 1 1 calc R . .
C18 C 0.9144(2) 0.8027(3) -0.02199(18) 0.0499(8) Uani 1 1 d . . .
C19 C 0.9402(2) 0.6746(3) 0.0109(2) 0.0664(9) Uani 1 1 d . . .
H19 H 0.9894 0.6266 -0.0161 0.080 Uiso 1 1 calc R . .
C20 C 0.8941(2) 0.6207(3) 0.0814(2) 0.0630(9) Uani 1 1 d . . .
H20 H 0.9120 0.5361 0.1020 0.076 Uiso 1 1 calc R . .
C21 C 0.8170(2) 1.3400(3) -0.2347(2) 0.0573(8) Uani 1 1 d . . .
H21 H 0.8331 1.3570 -0.2935 0.069 Uiso 1 1 calc R . .
C22 C 0.7629(2) 1.4294(3) -0.1891(2) 0.0615(9) Uani 1 1 d . . .
H22 H 0.7422 1.5079 -0.2170 0.074 Uiso 1 1 calc R . .
C23 C 0.7376(2) 1.4048(3) -0.09918(19) 0.0517(8) Uani 1 1 d . . .
C24 C 0.6793(2) 1.4962(3) -0.0530(2) 0.0696(10) Uani 1 1 d . . .
H24 H 0.6587 1.5740 -0.0817 0.084 Uiso 1 1 calc R . .
C25 C 0.5625(3) 0.6626(3) 0.3966(2) 0.0871(12) Uani 1 1 d . . .
H25A H 0.6179 0.6608 0.4358 0.131 Uiso 1 1 calc R . .
H25B H 0.5049 0.6519 0.4306 0.131 Uiso 1 1 calc R . .
H25C H 0.5602 0.7469 0.3656 0.131 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0571(13) 0.0439(12) 0.0668(13) 0.0155(10) 0.0150(11) 0.0030(10)
O2 0.0742(16) 0.0446(13) 0.1010(18) 0.0217(12) 0.0363(13) 0.0163(11)
O3 0.0587(13) 0.0627(13) 0.0435(11) 0.0051(10) 0.0040(10) 0.0030(11)
N1 0.0548(16) 0.0400(14) 0.0595(15) 0.0142(12) 0.0118(13) 0.0107(12)
N2 0.0479(14) 0.0377(13) 0.0463(14) 0.0026(11) 0.0044(11) 0.0027(11)
C1 0.072(2) 0.065(2) 0.100(3) 0.030(2) 0.020(2) -0.0045(18)
C2 0.0469(18) 0.0505(18) 0.0617(19) 0.0079(16) 0.0073(15) -0.0041(15)
C3 0.055(2) 0.0380(17) 0.0556(19) 0.0084(15) 0.0058(15) -0.0001(16)
C4 0.0495(18) 0.0344(15) 0.0514(17) 0.0035(14) 0.0066(14) 0.0019(13)
C5 0.0443(17) 0.0391(16) 0.0509(18) 0.0000(13) 0.0073(14) 0.0015(13)
C6 0.0446(17) 0.0354(16) 0.0470(17) 0.0001(13) 0.0021(14) 0.0013(13)
C7 0.0386(16) 0.0426(16) 0.0435(16) 0.0009(14) -0.0021(13) -0.0048(13)
C8 0.0448(17) 0.0409(16) 0.0423(16) 0.0023(13) -0.0025(13) -0.0065(13)
C9 0.0502(18) 0.0394(16) 0.0454(18) 0.0010(14) -0.0075(14) -0.0036(13)
C10 0.074(2) 0.0407(16) 0.0496(19) -0.0022(14) -0.0004(16) 0.0038(16)
C11 0.089(3) 0.054(2) 0.057(2) -0.0083(17) 0.0041(18) 0.0071(19)
C12 0.093(3) 0.058(2) 0.072(2) -0.0128(19) -0.002(2) 0.0238(19)
C13 0.068(2) 0.100(3) 0.101(3) 0.024(2) -0.016(2) -0.017(2)
C14 0.0454(18) 0.0472(17) 0.0472(18) -0.0010(15) -0.0023(15) -0.0055(14)
C15 0.052(2) 0.062(2) 0.0600(19) 0.0088(16) 0.0101(16) 0.0035(16)
C16 0.0426(17) 0.0532(19) 0.0472(17) 0.0033(14) 0.0082(14) -0.0014(14)
C17 0.055(2) 0.056(2) 0.060(2) 0.0031(17) 0.0196(16) 0.0107(16)
C18 0.0515(19) 0.0427(17) 0.0557(19) 0.0029(14) 0.0112(16) 0.0068(14)
C19 0.072(2) 0.0479(19) 0.081(2) 0.0093(17) 0.0298(19) 0.0187(17)
C20 0.071(2) 0.0402(18) 0.078(2) 0.0103(16) 0.0230(19) 0.0164(16)
C21 0.062(2) 0.057(2) 0.0528(19) 0.0131(16) -0.0030(16) -0.0088(17)
C22 0.073(2) 0.0496(19) 0.062(2) 0.0147(17) -0.0140(18) 0.0006(17)
C23 0.060(2) 0.0406(17) 0.055(2) 0.0000(14) -0.0114(16) -0.0003(15)
C24 0.088(3) 0.0476(19) 0.073(2) 0.0006(18) -0.013(2) 0.0143(18)
C25 0.099(3) 0.076(2) 0.088(3) -0.011(2) 0.032(2) -0.006(2)
_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 C3 1.341(3) . ?
O1 C2 1.484(3) . ?
O2 C3 1.198(3) . ?
O3 C14 1.385(3) . ?
O3 C15 1.440(3) . ?
N1 C3 1.361(3) . ?
N1 C4 1.403(3) . ?
N1 H1 0.8600 . ?
N2 C7 1.328(3) . ?
N2 C6 1.375(3) . ?
C1 C2 1.508(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C13 1.503(4) . ?
C2 C25 1.506(4) . ?
C4 C5 1.364(3) . ?
C4 C20 1.415(4) . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C18 1.414(3) . ?
C7 C16 1.427(4) . ?
C7 C8 1.484(4) . ?
C8 C14 1.381(4) . ?
C8 C9 1.437(4) . ?
C9 C10 1.413(4) . ?
C9 C23 1.422(4) . ?
C10 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C24 1.351(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C21 1.402(4) . ?
C15 C16 1.496(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.359(4) . ?
C17 C18 1.401(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.413(4) . ?
C19 C20 1.355(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.356(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.420(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.406(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C3 O1 C2 121.2(2) . . ?
C14 O3 C15 112.2(2) . . ?
C3 N1 C4 127.2(2) . . ?
C3 N1 H1 116.4 . . ?
C4 N1 H1 116.4 . . ?
C7 N2 C6 118.2(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C13 109.2(2) . . ?
O1 C2 C25 110.0(2) . . ?
C13 C2 C25 112.7(3) . . ?
O1 C2 C1 102.4(2) . . ?
C13 C2 C1 111.2(3) . . ?
C25 C2 C1 110.8(3) . . ?
O2 C3 O1 126.3(3) . . ?
O2 C3 N1 125.3(3) . . ?
O1 C3 N1 108.4(2) . . ?
C5 C4 N1 124.7(2) . . ?
C5 C4 C20 119.5(2) . . ?
N1 C4 C20 115.7(2) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N2 C6 C5 117.7(2) . . ?
N2 C6 C18 122.2(2) . . ?
C5 C6 C18 120.1(2) . . ?
N2 C7 C16 122.6(2) . . ?
N2 C7 C8 120.1(2) . . ?
C16 C7 C8 117.2(2) . . ?
C14 C8 C9 118.0(2) . . ?
C14 C8 C7 116.7(2) . . ?
C9 C8 C7 125.2(2) . . ?
C10 C9 C23 116.4(3) . . ?
C10 C9 C8 124.5(2) . . ?
C23 C9 C8 119.0(2) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C24 C12 C11 118.8(3) . . ?
C24 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 O3 122.5(2) . . ?
C8 C14 C21 122.9(3) . . ?
O3 C14 C21 114.5(2) . . ?
O3 C15 C16 110.6(2) . . ?
O3 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C7 118.9(2) . . ?
C17 C16 C15 124.0(3) . . ?
C7 C16 C15 117.0(2) . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 124.1(3) . . ?
C17 C18 C6 117.8(3) . . ?
C19 C18 C6 118.1(2) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C4 121.1(3) . . ?
C19 C20 H20 119.5 . . ?
C4 C20 H20 119.5 . . ?
C22 C21 C14 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C14 C21 H21 120.2 . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 C9 119.9(3) . . ?
C22 C23 C9 119.6(3) . . ?
C12 C24 C23 121.8(3) . . ?
C12 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.77
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.037
;


data_s1
_database_code_depnum_ccdc_archive 'CCDC 866226'
#TrackingRef 'web_deposit_cif_file_0_DNYANESHWARKAND_1328771478.DK-02-157.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C24H14N2O3
_chemical_formula_sum            'C24 H14 N2 O3'
_chemical_formula_weight         378.38
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   C1C1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   12.720(7)
_cell_length_b                   18.426(10)
_cell_length_c                   9.036(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.238(9)
_cell_angle_gamma                90.00
_cell_volume                     1791.3(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Needles
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    calcd
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS
_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  ?
_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            8878
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4050
_reflns_number_gt                2911
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0531P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(13)
_refine_ls_number_reflns         4050
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.022
_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 0.2125(2) 0.08853(12) 0.5439(3) 0.0936(6) Uani 1 1 d . . .
O2 O 0.5050(2) 0.02059(11) 1.1005(3) 0.1045(7) Uani 1 1 d . . .
O3 O 0.02802(16) 0.31284(9) 0.9830(2) 0.0658(4) Uani 1 1 d . . .
N1 N 0.37132(18) 0.07441(11) 0.8328(2) 0.0632(5) Uani 1 1 d . . .
N2 N 0.22478(15) 0.17246(9) 0.8727(2) 0.0481(4) Uani 1 1 d . . .
C1 C 0.2623(3) -0.02859(16) 0.6894(5) 0.0881(9) Uani 1 1 d . . .
H1 H 0.2052 -0.0597 0.6024 0.106 Uiso 1 1 calc R . .
C2 C 0.2727(3) 0.04995(15) 0.6700(4) 0.0730(7) Uani 1 1 d . . .
C3 C 0.4074(2) 0.14872(14) 0.8685(3) 0.0582(6) Uani 1 1 d . . .
C4 C 0.32714(19) 0.19840(12) 0.8797(3) 0.0487(5) Uani 1 1 d . . .
C5 C 0.14741(18) 0.21998(11) 0.8753(2) 0.0468(5) Uani 1 1 d . . .
C6 C 0.03467(19) 0.19556(12) 0.8690(2) 0.0486(5) Uani 1 1 d . . .
C7 C -0.02300(19) 0.12533(11) 0.8111(3) 0.0507(5) Uani 1 1 d . . .
C8 C 0.0184(2) 0.07057(12) 0.7443(3) 0.0600(5) Uani 1 1 d . . .
H8 H 0.0877 0.0793 0.7376 0.072 Uiso 1 1 calc R . .
C9 C -0.0410(3) 0.00504(14) 0.6894(4) 0.0721(7) Uani 1 1 d . . .
H9 H -0.0102 -0.0305 0.6493 0.087 Uiso 1 1 calc R . .
C10 C -0.1473(3) -0.00889(15) 0.6931(4) 0.0786(8) Uani 1 1 d . . .
H10 H -0.1880 -0.0532 0.6532 0.094 Uiso 1 1 calc R . .
C11 C 0.4203(3) 0.01695(15) 0.9500(4) 0.0734(7) Uani 1 1 d . . .
C12 C 0.3467(3) -0.04725(16) 0.8491(5) 0.0847(8) Uani 1 1 d . . .
H12 H 0.3589 -0.0942 0.8934 0.102 Uiso 1 1 calc R . .
C13 C 0.1710(2) 0.29614(12) 0.8896(3) 0.0506(5) Uani 1 1 d . . .
C14 C 0.0747(2) 0.34462(12) 0.8846(3) 0.0625(6) Uani 1 1 d . . .
H14A H 0.1109 0.3916 0.9335 0.075 Uiso 1 1 calc R . .
H14B H 0.0070 0.3517 0.7644 0.075 Uiso 1 1 calc R . .
C15 C -0.0181(2) 0.24470(13) 0.9271(3) 0.0554(5) Uani 1 1 d . . .
C16 C -0.1909(3) 0.04164(17) 0.7543(3) 0.0743(7) Uani 1 1 d . . .
H16 H -0.2617 0.0318 0.7568 0.089 Uiso 1 1 calc R . .
C17 C -0.1309(2) 0.10968(13) 0.8151(3) 0.0607(6) Uani 1 1 d . . .
C18 C -0.1763(3) 0.16191(16) 0.8809(4) 0.0756(7) Uani 1 1 d . . .
H18 H -0.2456 0.1510 0.8863 0.091 Uiso 1 1 calc R . .
C19 C -0.1216(2) 0.22759(16) 0.9366(3) 0.0709(7) Uani 1 1 d . . .
H19 H -0.1525 0.2612 0.9809 0.085 Uiso 1 1 calc R . .
C20 C 0.2745(2) 0.32160(12) 0.9025(3) 0.0547(5) Uani 1 1 d . . .
H20 H 0.2903 0.3712 0.9132 0.066 Uiso 1 1 calc R . .
C21 C 0.3593(2) 0.27301(13) 0.8999(3) 0.0540(5) Uani 1 1 d . . .
C22 C 0.4706(2) 0.29466(15) 0.9162(3) 0.0676(6) Uani 1 1 d . . .
H22 H 0.4920 0.3436 0.9302 0.081 Uiso 1 1 calc R . .
C23 C 0.5477(2) 0.24498(19) 0.9116(4) 0.0814(8) Uani 1 1 d . . .
H23 H 0.6226 0.2598 0.9266 0.098 Uiso 1 1 calc R . .
C24 C 0.5146(2) 0.17164(17) 0.8845(4) 0.0761(7) Uani 1 1 d . . .
H24 H 0.5665 0.1382 0.8773 0.091 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0908(15) 0.0928(14) 0.0745(12) -0.0117(11) 0.0289(11) 0.0133(12)
O2 0.0920(16) 0.0910(14) 0.0987(16) 0.0068(12) 0.0294(14) 0.0282(13)
O3 0.0694(11) 0.0584(9) 0.0814(10) -0.0081(8) 0.0481(9) 0.0094(8)
N1 0.0509(11) 0.0601(12) 0.0772(12) -0.0079(10) 0.0332(10) 0.0118(9)
N2 0.0437(10) 0.0474(10) 0.0528(9) -0.0023(7) 0.0255(8) 0.0029(8)
C1 0.0790(19) 0.0686(17) 0.116(3) -0.0279(17) 0.052(2) 0.0001(15)
C2 0.0646(16) 0.0732(16) 0.0812(17) -0.0184(15) 0.0388(15) 0.0073(15)
C3 0.0443(12) 0.0640(15) 0.0654(14) -0.0074(11) 0.0285(11) 0.0030(11)
C4 0.0418(11) 0.0540(12) 0.0513(10) -0.0061(9) 0.0256(9) -0.0017(10)
C5 0.0436(11) 0.0471(12) 0.0484(11) -0.0031(9) 0.0236(9) 0.0031(9)
C6 0.0434(11) 0.0495(11) 0.0523(11) 0.0029(9) 0.0252(9) 0.0063(9)
C7 0.0447(11) 0.0511(12) 0.0492(10) 0.0069(9) 0.0203(9) 0.0028(10)
C8 0.0530(13) 0.0549(13) 0.0676(13) -0.0035(10) 0.0290(11) -0.0026(11)
C9 0.0716(17) 0.0571(14) 0.0724(15) -0.0069(11) 0.0282(13) -0.0073(13)
C10 0.0747(19) 0.0694(17) 0.0737(17) -0.0005(13) 0.0274(15) -0.0248(15)
C11 0.0575(15) 0.0735(17) 0.091(2) 0.0022(14) 0.0411(15) 0.0226(14)
C12 0.087(2) 0.0565(15) 0.128(3) -0.0070(17) 0.069(2) 0.0141(15)
C13 0.0535(13) 0.0449(12) 0.0550(11) -0.0039(9) 0.0300(10) 0.0024(10)
C14 0.0662(15) 0.0462(12) 0.0804(16) -0.0030(11) 0.0425(13) 0.0052(11)
C15 0.0509(13) 0.0579(13) 0.0607(13) 0.0031(10) 0.0320(11) 0.0081(11)
C16 0.0601(15) 0.0848(19) 0.0707(15) 0.0104(14) 0.0300(12) -0.0131(14)
C17 0.0492(13) 0.0667(15) 0.0648(13) 0.0113(11) 0.0296(11) -0.0013(11)
C18 0.0586(15) 0.092(2) 0.0947(18) 0.0139(15) 0.0534(14) 0.0059(15)
C19 0.0693(17) 0.0729(17) 0.0899(18) 0.0045(13) 0.0554(16) 0.0109(14)
C20 0.0604(13) 0.0456(12) 0.0597(13) -0.0060(9) 0.0331(11) -0.0058(11)
C21 0.0500(12) 0.0594(13) 0.0536(11) -0.0066(9) 0.0284(10) -0.0060(10)
C22 0.0606(15) 0.0713(16) 0.0776(16) -0.0120(12) 0.0413(13) -0.0185(13)
C23 0.0540(15) 0.099(2) 0.104(2) -0.0135(16) 0.0509(16) -0.0130(15)
C24 0.0562(15) 0.085(2) 0.0984(19) -0.0134(16) 0.0490(14) 0.0015(15)
_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 C2 1.208(3) . ?
O2 C11 1.205(4) . ?
O3 C15 1.363(3) . ?
O3 C14 1.431(3) . ?
N1 C11 1.388(3) . ?
N1 C2 1.404(3) . ?
N1 C3 1.425(3) . ?
N2 C5 1.327(2) . ?
N2 C4 1.357(3) . ?
C1 C12 1.304(4) . ?
C1 C2 1.472(4) . ?
C1 H1 0.9300 . ?
C3 C24 1.360(3) . ?
C3 C4 1.414(3) . ?
C4 C21 1.418(3) . ?
C5 C13 1.426(3) . ?
C5 C6 1.475(3) . ?
C6 C15 1.386(3) . ?
C6 C7 1.441(3) . ?
C7 C8 1.414(3) . ?
C7 C17 1.421(3) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(4) . ?
C9 H9 0.9300 . ?
C10 C16 1.345(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.482(4) . ?
C12 H12 0.9300 . ?
C13 C20 1.343(3) . ?
C13 C14 1.497(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C19 1.401(3) . ?
C16 C17 1.418(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.408(4) . ?
C18 C19 1.352(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.413(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(4) . ?
C22 C23 1.357(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 C14 112.67(17) . . ?
C11 N1 C2 109.9(2) . . ?
C11 N1 C3 126.9(2) . . ?
C2 N1 C3 123.1(2) . . ?
C5 N2 C4 117.99(18) . . ?
C12 C1 C2 108.5(3) . . ?
C12 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
O1 C2 N1 124.2(3) . . ?
O1 C2 C1 129.7(3) . . ?
N1 C2 C1 106.1(3) . . ?
C24 C3 C4 120.9(2) . . ?
C24 C3 N1 120.4(2) . . ?
C4 C3 N1 118.7(2) . . ?
N2 C4 C3 118.7(2) . . ?
N2 C4 C21 123.47(18) . . ?
C3 C4 C21 117.83(19) . . ?
N2 C5 C13 121.94(19) . . ?
N2 C5 C6 120.88(18) . . ?
C13 C5 C6 117.16(17) . . ?
C15 C6 C7 117.95(19) . . ?
C15 C6 C5 116.31(19) . . ?
C7 C6 C5 125.73(17) . . ?
C8 C7 C17 116.8(2) . . ?
C8 C7 C6 124.24(18) . . ?
C17 C7 C6 118.97(18) . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C16 C10 C9 120.0(3) . . ?
C16 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O2 C11 N1 125.9(3) . . ?
O2 C11 C12 129.0(3) . . ?
N1 C11 C12 105.1(3) . . ?
C1 C12 C11 110.3(3) . . ?
C1 C12 H12 124.8 . . ?
C11 C12 H12 124.8 . . ?
C20 C13 C5 120.0(2) . . ?
C20 C13 C14 122.9(2) . . ?
C5 C13 C14 117.09(19) . . ?
O3 C14 C13 109.92(18) . . ?
O3 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
O3 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O3 C15 C6 122.9(2) . . ?
O3 C15 C19 114.6(2) . . ?
C6 C15 C19 122.5(2) . . ?
C10 C16 C17 121.1(3) . . ?
C10 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 C7 119.5(2) . . ?
C16 C17 C7 119.8(2) . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C15 119.5(2) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?
C13 C20 C21 120.0(2) . . ?
C13 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 123.8(2) . . ?
C20 C21 C4 116.5(2) . . ?
C22 C21 C4 119.7(2) . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C3 C24 C23 120.6(2) . . ?
C3 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032