# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_ard_pm_pph_0m
_audit_block_doi                 10.5517/cc13mvdz
_database_code_depnum_ccdc_archive 'CCDC 1031971'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 N2 O4'
_chemical_formula_sum            'C25 H18 N2 O4'
_chemical_formula_weight         410.41

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           triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2667(4)
_cell_length_b                   10.2113(5)
_cell_length_c                   12.2305(6)
_cell_angle_alpha                98.507(2)
_cell_angle_beta                 99.326(2)
_cell_angle_gamma                97.391(2)
_cell_volume                     995.17(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Niddle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   ?
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11405
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.70
_reflns_number_total             3695
_reflns_number_gt                2908
_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    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.0800P)²+0.5000P] 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         3695
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C 0.3649(3) 0.2021(3) 0.23795(19) 0.0543(6) Uani 1 1 d . . .
H1 H 0.3619 0.2936 0.2436 0.065 Uiso 1 1 calc R . .
C2 C 0.3871(3) 0.1279(3) 0.1386(2) 0.0678(7) Uani 1 1 d . . .
H2 H 0.3978 0.1696 0.0769 0.081 Uiso 1 1 calc R . .
C3 C 0.3934(3) -0.0071(3) 0.1307(2) 0.0632(7) Uani 1 1 d . . .
H3 H 0.4084 -0.0563 0.0638 0.076 Uiso 1 1 calc R . .
C4 C 0.3778(3) -0.0691(3) 0.2209(2) 0.0586(6) Uani 1 1 d . . .
H4 H 0.3833 -0.1602 0.2154 0.070 Uiso 1 1 calc R . .
C5 C 0.3537(3) 0.0032(2) 0.3208(2) 0.0530(6) Uani 1 1 d . . .
H5 H 0.3421 -0.0391 0.3820 0.064 Uiso 1 1 calc R . .
C6 C 0.3472(2) 0.1390(2) 0.32835(17) 0.0427(5) Uani 1 1 d . . .
C7 C 0.2706(3) 0.1774(2) 0.52148(16) 0.0400(5) Uani 1 1 d . . .
C8 C 0.2396(3) 0.2849(2) 0.58985(17) 0.0402(5) Uani 1 1 d . . .
C9 C 0.2700(3) 0.3925(2) 0.53117(18) 0.0455(5) Uani 1 1 d . . .
C10 C 0.2571(4) 0.5372(2) 0.5644(2) 0.0620(7) Uani 1 1 d . . .
H10A H 0.2766 0.5843 0.5043 0.093 Uiso 1 1 calc R . .
H10B H 0.3382 0.5752 0.6307 0.093 Uiso 1 1 calc R . .
H10C H 0.1480 0.5449 0.5796 0.093 Uiso 1 1 calc R . .
C11 C 0.1803(3) 0.2702(2) 0.69790(16) 0.0399(5) Uani 1 1 d . . .
C12 C 0.2927(3) 0.3658(2) 0.80005(18) 0.0480(5) Uani 1 1 d . . .
C13 C 0.1945(3) 0.4662(2) 0.84403(16) 0.0432(5) Uani 1 1 d . . .
C14 C 0.2434(3) 0.5725(2) 0.93409(18) 0.0516(6) Uani 1 1 d . . .
H14 H 0.3519 0.5914 0.9739 0.062 Uiso 1 1 calc R . .
C15 C 0.1254(4) 0.6485(2) 0.96207(18) 0.0552(6) Uani 1 1 d . . .
H15 H 0.1550 0.7196 1.0222 0.066 Uiso 1 1 calc R . .
C16 C -0.0359(3) 0.6217(2) 0.90303(19) 0.0548(6) Uani 1 1 d . . .
H16 H -0.1125 0.6752 0.9239 0.066 Uiso 1 1 calc R . .
C17 C -0.0850(3) 0.5170(2) 0.81357(18) 0.0479(5) Uani 1 1 d . . .
H17 H -0.1934 0.4991 0.7736 0.057 Uiso 1 1 calc R . .
C18 C 0.0326(3) 0.4394(2) 0.78541(16) 0.0404(5) Uani 1 1 d . . .
C19 C 0.0097(3) 0.3183(2) 0.69806(16) 0.0398(5) Uani 1 1 d . . .
C20 C 0.1706(3) 0.1237(2) 0.71012(16) 0.0404(5) Uani 1 1 d . . .
C21 C 0.2045(3) 0.0261(2) 0.63474(16) 0.0405(5) Uani 1 1 d . . .
C22 C 0.1947(3) -0.1178(2) 0.64418(18) 0.0478(5) Uani 1 1 d . . .
H22A H 0.1419 -0.1717 0.5721 0.057 Uiso 1 1 calc R . .
H22B H 0.3063 -0.1385 0.6620 0.057 Uiso 1 1 calc R . .
C23 C 0.1022(5) -0.1542(3) 0.7300(3) 0.0835(10) Uani 1 1 d . . .
H23A H 0.1377 -0.2345 0.7529 0.100 Uiso 1 1 calc R . .
H23B H -0.0142 -0.1773 0.6953 0.100 Uiso 1 1 calc R . .
C24 C 0.1158(4) -0.0545(2) 0.8314(2) 0.0619(7) Uani 1 1 d . . .
H24A H 0.2155 -0.0607 0.8833 0.074 Uiso 1 1 calc R . .
H24B H 0.0219 -0.0772 0.8671 0.074 Uiso 1 1 calc R . .
C25 C 0.1220(3) 0.0876(2) 0.81317(17) 0.0475(5) Uani 1 1 d . . .
N1 N 0.3179(2) 0.21624(17) 0.42874(14) 0.0431(4) Uani 1 1 d . . .
N2 N 0.3163(2) 0.35193(18) 0.43466(16) 0.0491(5) Uani 1 1 d . . .
O1 O 0.2565(2) 0.04797(14) 0.53666(12) 0.0485(4) Uani 1 1 d . . .
O2 O 0.4345(2) 0.3580(2) 0.83483(16) 0.0785(6) Uani 1 1 d . . .
O3 O -0.11719(19) 0.26548(15) 0.63556(13) 0.0532(4) Uani 1 1 d . . .
O4 O 0.0925(3) 0.17463(18) 0.88372(14) 0.0738(6) Uani 1 1 d . . .


_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
C1 C6 1.378(3) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.431(3) . ?
C7 N1 1.354(3) . ?
C7 O1 1.355(2) . ?
C7 C8 1.356(3) . ?
C8 C9 1.416(3) . ?
C8 C11 1.503(3) . ?
C9 N2 1.324(3) . ?
C9 C10 1.496(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C20 1.519(3) . ?
C11 C12 1.551(3) . ?
C11 C19 1.552(3) . ?
C12 O2 1.197(3) . ?
C12 C13 1.480(3) . ?
C13 C18 1.385(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.480(3) . ?
C19 O3 1.203(2) . ?
C20 C21 1.343(3) . ?
C20 C25 1.466(3) . ?
C21 O1 1.377(2) . ?
C21 C22 1.484(3) . ?
C22 C23 1.458(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.463(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.496(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O4 1.221(3) . ?
N1 N2 1.379(2) . ?

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
C6 C1 C2 119.3(2) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 N1 118.4(2) . . ?
C5 C6 N1 121.0(2) . . ?
N1 C7 O1 122.05(17) . . ?
N1 C7 C8 109.77(18) . . ?
O1 C7 C8 128.18(19) . . ?
C7 C8 C9 103.80(18) . . ?
C7 C8 C11 121.22(19) . . ?
C9 C8 C11 134.93(18) . . ?
N2 C9 C8 111.53(18) . . ?
N2 C9 C10 119.5(2) . . ?
C8 C9 C10 129.0(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C20 107.57(15) . . ?
C8 C11 C12 111.79(18) . . ?
C20 C11 C12 112.72(17) . . ?
C8 C11 C19 110.86(16) . . ?
C20 C11 C19 111.53(17) . . ?
C12 C11 C19 102.39(15) . . ?
O2 C12 C13 127.2(2) . . ?
O2 C12 C11 124.72(19) . . ?
C13 C12 C11 108.09(18) . . ?
C18 C13 C14 120.5(2) . . ?
C18 C13 C12 110.63(17) . . ?
C14 C13 C12 128.8(2) . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C16 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 117.7(2) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C17 C18 C13 121.44(19) . . ?
C17 C18 C19 128.3(2) . . ?
C13 C18 C19 110.24(17) . . ?
O3 C19 C18 127.01(19) . . ?
O3 C19 C11 124.66(17) . . ?
C18 C19 C11 108.31(17) . . ?
C21 C20 C25 118.07(19) . . ?
C21 C20 C11 125.12(19) . . ?
C25 C20 C11 116.80(17) . . ?
C20 C21 O1 123.59(19) . . ?
C20 C21 C22 126.18(19) . . ?
O1 C21 C22 110.22(16) . . ?
C23 C22 C21 112.93(19) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 117.6(2) . . ?
C22 C23 H23A 107.9 . . ?
C24 C23 H23A 107.9 . . ?
C22 C23 H23B 107.9 . . ?
C24 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C23 C24 C25 115.4(2) . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
O4 C25 C20 119.4(2) . . ?
O4 C25 C24 121.4(2) . . ?
C20 C25 C24 119.11(18) . . ?
C7 N1 N2 109.20(16) . . ?
C7 N1 C6 130.71(18) . . ?
N2 N1 C6 119.63(17) . . ?
C9 N2 N1 105.69(17) . . ?
C7 O1 C21 114.30(15) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_ncpp
_database_code_depnum_ccdc_archive 'CCDC 1031972'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 N2 O4'
_chemical_formula_weight         320.30

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   16.5569(8)
_cell_length_b                   7.4472(4)
_cell_length_c                   12.9479(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.196(2)
_cell_angle_gamma                90.00
_cell_volume                     1575.99(14)
_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       Niddle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9932
_exptl_absorpt_correction_T_max  0.9951
_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  ?
_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            19031
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         27.71
_reflns_number_total             3589
_reflns_number_gt                2868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0580P)²+0.3767P] 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         3589
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1083
_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
O3 O 0.06449(6) 0.09417(14) 0.15084(8) 0.0426(3) Uani 1 1 d . . .
O2] O 0.24128(6) 0.26610(15) -0.03205(8) 0.0433(3) Uani 1 1 d . . .
O1 O 0.32396(7) -0.02276(17) 0.29331(8) 0.0532(3) Uani 1 1 d . . .
O5 O 0.08026(7) 0.39104(16) -0.05586(10) 0.0529(3) Uani 1 1 d . . .
O4 O 0.29259(8) 0.47057(18) 0.24452(12) 0.0695(4) Uani 1 1 d . . .
N1 N 0.06586(7) -0.18109(18) 0.06665(10) 0.0433(3) Uani 1 1 d . . .
N2 N 0.12519(8) -0.27659(19) 0.02940(10) 0.0427(3) Uani 1 1 d . . .
C008 C 0.28137(7) 0.20312(18) 0.04579(10) 0.0313(3) Uani 1 1 d . . .
C13 C 0.10558(8) -0.03801(19) 0.10646(10) 0.0350(3) Uani 1 1 d . . .
C15 C 0.19913(8) -0.19588(19) 0.04626(11) 0.0365(3) Uani 1 1 d . . .
C10 C 0.24544(7) 0.11392(18) 0.13645(10) 0.0299(3) Uani 1 1 d . . .
C14 C 0.18852(7) -0.03737(18) 0.09785(10) 0.0315(3) Uani 1 1 d . . .
C12 C 0.11387(8) 0.2318(2) 0.18830(10) 0.0354(3) Uani 1 1 d . . .
C7 C 0.32352(8) 0.05463(19) 0.21160(11) 0.0351(3) Uani 1 1 d . . .
C1 C 0.37130(8) 0.1945(2) 0.06963(11) 0.0369(3) Uani 1 1 d . . .
C11 C 0.19439(8) 0.24562(18) 0.18652(10) 0.0326(3) Uani 1 1 d . . .
C6 C 0.39586(8) 0.1085(2) 0.16413(12) 0.0380(3) Uani 1 1 d . . .
C17 C 0.22285(10) 0.4143(2) 0.23575(12) 0.0433(4) Uani 1 1 d . . .
C19 C 0.07691(10) 0.3887(2) 0.23450(12) 0.0463(4) Uani 1 1 d . . .
H19A H 0.0493 0.3523 0.2917 0.056 Uiso 1 1 calc R . .
H19B H 0.0384 0.4509 0.1823 0.056 Uiso 1 1 calc R . .
C5 C 0.47856(9) 0.0841(2) 0.20263(15) 0.0503(4) Uani 1 1 d . . .
H5 H 0.4955 0.0251 0.2657 0.060 Uiso 1 1 calc R . .
C18 C 0.15110(11) 0.5057(2) 0.27326(12) 0.0507(4) Uani 1 1 d . . .
H18A H 0.1434 0.6259 0.2444 0.061 Uiso 1 1 calc R . .
H18B H 0.1600 0.5138 0.3490 0.061 Uiso 1 1 calc R . .
C16 C 0.27267(10) -0.2749(2) 0.01141(15) 0.0525(4) Uani 1 1 d . . .
H16A H 0.2585 -0.3878 -0.0225 0.079 Uiso 1 1 calc R . .
H16B H 0.3145 -0.2934 0.0710 0.079 Uiso 1 1 calc R . .
H16C H 0.2926 -0.1945 -0.0368 0.079 Uiso 1 1 calc R . .
C3 C 0.50933(9) 0.2389(3) 0.04998(17) 0.0622(5) Uani 1 1 d . . .
H3 H 0.5485 0.2837 0.0127 0.075 Uiso 1 1 calc R . .
C2 C 0.42750(9) 0.2618(2) 0.01058(14) 0.0506(4) Uani 1 1 d . . .
H2 H 0.4107 0.3199 -0.0528 0.061 Uiso 1 1 calc R . .
C4 C 0.53450(9) 0.1507(3) 0.14379(17) 0.0603(5) Uani 1 1 d . . .
H4 H 0.5901 0.1360 0.1676 0.072 Uiso 1 1 calc R . .
H12 H 0.1122(12) -0.385(3) -0.0011(15) 0.064(6) Uiso 1 1 d . . .
H20A H 0.0376(14) 0.314(3) -0.0538(17) 0.080(7) Uiso 1 1 d . . .
H20B H 0.1267(15) 0.322(3) -0.0490(17) 0.083(7) Uiso 1 1 d . . .


_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
O3 C12 1.3519(18) . ?
O3 C13 1.3736(17) . ?
O2] C008 1.2093(16) . ?
O1 C7 1.2037(17) . ?
O4 C17 1.216(2) . ?
N1 C13 1.3135(19) . ?
N1 N2 1.3619(18) . ?
N2 C15 1.3499(18) . ?
C008 C1 1.4730(17) . ?
C008 C10 1.5481(18) . ?
C13 C14 1.3954(17) . ?
C15 C14 1.381(2) . ?
C15 C16 1.486(2) . ?
C10 C14 1.5024(18) . ?
C10 C11 1.5073(18) . ?
C10 C7 1.5527(18) . ?
C12 C11 1.3409(18) . ?
C12 C19 1.488(2) . ?
C7 C6 1.4861(19) . ?
C1 C6 1.384(2) . ?
C1 C2 1.389(2) . ?
C11 C17 1.453(2) . ?
C6 C5 1.3922(19) . ?
C17 C18 1.515(2) . ?
C19 C18 1.524(2) . ?
C5 C4 1.382(3) . ?
C3 C2 1.380(2) . ?
C3 C4 1.385(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
C12 O3 C13 112.45(10) . . ?
C13 N1 N2 102.61(11) . . ?
C15 N2 N1 113.39(13) . . ?
O2] C008 C1 126.39(12) . . ?
O2] C008 C10 124.90(11) . . ?
C1 C008 C10 108.69(11) . . ?
N1 C13 O3 119.68(12) . . ?
N1 C13 C14 114.13(13) . . ?
O3 C13 C14 126.19(12) . . ?
N2 C15 C14 106.06(12) . . ?
N2 C15 C16 122.72(14) . . ?
C14 C15 C16 131.22(13) . . ?
C14 C10 C11 105.43(10) . . ?
C14 C10 C008 111.48(10) . . ?
C11 C10 C008 110.90(11) . . ?
C14 C10 C7 114.23(11) . . ?
C11 C10 C7 112.55(11) . . ?
C008 C10 C7 102.41(10) . . ?
C15 C14 C13 103.80(12) . . ?
C15 C14 C10 132.87(12) . . ?
C13 C14 C10 123.30(12) . . ?
C11 C12 O3 126.72(13) . . ?
C11 C12 C19 114.86(13) . . ?
O3 C12 C19 118.39(12) . . ?
O1 C7 C6 126.91(13) . . ?
O1 C7 C10 125.06(12) . . ?
C6 C7 C10 108.02(11) . . ?
C6 C1 C2 121.74(13) . . ?
C6 C1 C008 110.48(12) . . ?
C2 C1 C008 127.78(14) . . ?
C12 C11 C17 108.21(13) . . ?
C12 C11 C10 125.79(12) . . ?
C17 C11 C10 125.91(12) . . ?
C1 C6 C5 120.68(14) . . ?
C1 C6 C7 110.39(11) . . ?
C5 C6 C7 128.93(15) . . ?
O4 C17 C11 125.11(15) . . ?
O4 C17 C18 126.64(15) . . ?
C11 C17 C18 108.25(13) . . ?
C12 C19 C18 102.70(12) . . ?
C4 C5 C6 117.60(16) . . ?
C17 C18 C19 105.64(13) . . ?
C2 C3 C4 121.53(16) . . ?
C3 C2 C1 117.15(16) . . ?
C5 C4 C3 121.29(14) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.71
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1031973'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         362.37

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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                   11.332(2)
_cell_length_b                   9.1756(16)
_cell_length_c                   17.706(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.540(6)
_cell_angle_gamma                90.00
_cell_volume                     1782.1(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       Niddle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_T_max  0.9798
_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  ?
_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            20810
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4027
_reflns_number_gt                3210
_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    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.0588P)²+0.5640P] 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         4027
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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
O4 O 0.31675(9) 0.25243(12) 0.33713(6) 0.0392(3) Uani 1 1 d . . .
O3 O -0.08205(9) 0.18518(13) 0.18038(6) 0.0425(3) Uani 1 1 d . . .
O2 O 0.00555(10) -0.02850(12) 0.34516(8) 0.0516(3) Uani 1 1 d . . .
O1 O -0.01915(11) 0.48085(12) 0.30728(8) 0.0525(3) Uani 1 1 d . . .
N2 N 0.27619(12) 0.28890(16) 0.51946(8) 0.0424(3) Uani 1 1 d . . .
C10 C 0.10994(12) 0.21201(15) 0.26521(8) 0.0292(3) Uani 1 1 d . . .
C1 C 0.05188(11) 0.22945(15) 0.33301(8) 0.0286(3) Uani 1 1 d . . .
C15 C 0.23040(12) 0.22583(15) 0.26979(8) 0.0313(3) Uani 1 1 d . . .
C3 C -0.15755(12) 0.29925(17) 0.33199(8) 0.0348(3) Uani 1 1 d . . .
C13 C 0.19712(13) 0.23034(16) 0.12353(9) 0.0352(3) Uani 1 1 d . . .
C8 C -0.14948(12) 0.15022(17) 0.34461(8) 0.0350(3) Uani 1 1 d . . .
C11 C 0.02903(12) 0.18018(16) 0.18918(8) 0.0315(3) Uani 1 1 d . . .
C12 C 0.08499(13) 0.13802(19) 0.12397(9) 0.0366(3) Uani 1 1 d . . .
C19 C 0.15254(12) 0.25305(15) 0.40505(8) 0.0301(3) Uani 1 1 d . . .
C18 C 0.27410(12) 0.26170(16) 0.40292(8) 0.0329(3) Uani 1 1 d . . .
N1 N 0.35141(11) 0.28287(16) 0.47041(8) 0.0418(3) Uani 1 1 d . . .
C9 C -0.02788(12) 0.09616(16) 0.34160(8) 0.0329(3) Uani 1 1 d . . .
C20 C 0.15711(13) 0.27238(17) 0.48314(9) 0.0363(3) Uani 1 1 d . . .
C14 C 0.28739(13) 0.2143(2) 0.20281(9) 0.0387(4) Uani 1 1 d . . .
C2 C -0.04117(12) 0.35685(16) 0.32090(8) 0.0328(3) Uani 1 1 d . . .
C21 C 0.06072(18) 0.2789(3) 0.52659(12) 0.0554(5) Uani 1 1 d . . .
C7 C -0.24902(15) 0.0715(2) 0.35490(11) 0.0502(4) Uani 1 1 d . . .
C16 C 0.25576(18) 0.1754(3) 0.06010(11) 0.0525(5) Uani 1 1 d . . .
C17 C 0.1599(2) 0.3894(2) 0.10768(13) 0.0561(5) Uani 1 1 d . . .
C4 C -0.26485(14) 0.3748(2) 0.32882(10) 0.0481(4) Uani 1 1 d . . .
C6 C -0.35528(15) 0.1477(3) 0.35233(12) 0.0604(5) Uani 1 1 d . . .
C5 C -0.36298(15) 0.2963(3) 0.33934(12) 0.0587(5) Uani 1 1 d . . .
H7 H -0.2407(17) -0.031(2) 0.3633(11) 0.053(5) Uiso 1 1 d . . .
H4 H -0.2687(18) 0.481(2) 0.3194(12) 0.061(6) Uiso 1 1 d . . .
H5 H -0.442(2) 0.342(2) 0.3358(13) 0.070(6) Uiso 1 1 d . . .
H6 H -0.425(2) 0.096(3) 0.3580(13) 0.076(7) Uiso 1 1 d . . .
H16C H 0.323(2) 0.239(2) 0.0583(14) 0.077(7) Uiso 1 1 d . . .
H17B H 0.096(2) 0.397(3) 0.0567(15) 0.081(7) Uiso 1 1 d . . .
H16B H 0.195(2) 0.181(3) 0.0073(15) 0.076(7) Uiso 1 1 d . . .
H17A H 0.231(2) 0.447(3) 0.1033(14) 0.086(7) Uiso 1 1 d . . .
H17C H 0.127(2) 0.429(2) 0.1515(13) 0.069(6) Uiso 1 1 d . . .
H16A H 0.283(2) 0.070(3) 0.0717(13) 0.073(6) Uiso 1 1 d . . .
H2 H 0.3106(19) 0.304(2) 0.5707(13) 0.059(6) Uiso 1 1 d . . .
H21B H -0.009(3) 0.328(3) 0.4989(18) 0.101(9) Uiso 1 1 d . . .
H21C H 0.086(3) 0.306(4) 0.577(2) 0.134(12) Uiso 1 1 d . . .
H21A H 0.023(3) 0.185(4) 0.5245(19) 0.123(12) Uiso 1 1 d . . .
H12B H 0.0235(16) 0.1418(19) 0.0744(11) 0.043(4) Uiso 1 1 d . . .
H14B H 0.352(2) 0.287(2) 0.2114(12) 0.059(6) Uiso 1 1 d . . .
H12A H 0.1110(17) 0.035(2) 0.1332(11) 0.051(5) Uiso 1 1 d . . .
H14A H 0.3263(17) 0.119(2) 0.2080(11) 0.055(5) Uiso 1 1 d . . .


_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
O4 C15 1.3612(18) . ?
O4 C18 1.3713(17) . ?
O3 C11 1.2297(16) . ?
O2 C9 1.2016(18) . ?
O1 C2 1.2021(18) . ?
N2 C20 1.350(2) . ?
N2 N1 1.3623(18) . ?
C10 C15 1.3530(18) . ?
C10 C11 1.455(2) . ?
C10 C1 1.5153(18) . ?
C1 C19 1.4982(19) . ?
C1 C9 1.5507(19) . ?
C1 C2 1.5527(19) . ?
C15 C14 1.4896(19) . ?
C3 C8 1.385(2) . ?
C3 C4 1.389(2) . ?
C3 C2 1.4789(19) . ?
C13 C14 1.522(2) . ?
C13 C17 1.525(2) . ?
C13 C16 1.527(2) . ?
C13 C12 1.529(2) . ?
C8 C7 1.390(2) . ?
C8 C9 1.4781(19) . ?
C11 C12 1.5009(19) . ?
C19 C20 1.382(2) . ?
C19 C18 1.3898(19) . ?
C18 N1 1.307(2) . ?
C20 C21 1.487(2) . ?
C7 C6 1.384(3) . ?
C4 C5 1.376(3) . ?
C6 C5 1.382(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
C15 O4 C18 115.22(10) . . ?
C20 N2 N1 113.73(13) . . ?
C15 C10 C11 117.78(12) . . ?
C15 C10 C1 125.08(12) . . ?
C11 C10 C1 117.12(11) . . ?
C19 C1 C10 107.49(10) . . ?
C19 C1 C9 111.62(11) . . ?
C10 C1 C9 111.96(11) . . ?
C19 C1 C2 110.75(11) . . ?
C10 C1 C2 112.64(11) . . ?
C9 C1 C2 102.41(10) . . ?
C10 C15 O4 124.19(12) . . ?
C10 C15 C14 125.32(13) . . ?
O4 C15 C14 110.49(11) . . ?
C8 C3 C4 121.42(14) . . ?
C8 C3 C2 110.45(12) . . ?
C4 C3 C2 128.11(15) . . ?
C14 C13 C17 110.67(15) . . ?
C14 C13 C16 109.30(13) . . ?
C17 C13 C16 109.38(15) . . ?
C14 C13 C12 107.98(12) . . ?
C17 C13 C12 109.81(13) . . ?
C16 C13 C12 109.68(14) . . ?
C3 C8 C7 120.78(14) . . ?
C3 C8 C9 110.48(12) . . ?
C7 C8 C9 128.69(15) . . ?
O3 C11 C10 119.79(12) . . ?
O3 C11 C12 121.93(13) . . ?
C10 C11 C12 118.26(12) . . ?
C11 C12 C13 111.93(12) . . ?
C20 C19 C18 103.38(13) . . ?
C20 C19 C1 134.39(12) . . ?
C18 C19 C1 122.22(12) . . ?
N1 C18 O4 119.19(12) . . ?
N1 C18 C19 115.17(13) . . ?
O4 C18 C19 125.63(13) . . ?
C18 N1 N2 101.88(12) . . ?
O2 C9 C8 127.01(13) . . ?
O2 C9 C1 124.90(12) . . ?
C8 C9 C1 108.09(12) . . ?
N2 C20 C19 105.84(13) . . ?
N2 C20 C21 121.70(15) . . ?
C19 C20 C21 132.46(15) . . ?
C15 C14 C13 113.70(12) . . ?
O1 C2 C3 127.00(13) . . ?
O1 C2 C1 124.91(12) . . ?
C3 C2 C1 108.06(12) . . ?
C6 C7 C8 117.46(19) . . ?
C5 C4 C3 117.53(18) . . ?
C5 C6 C7 121.50(16) . . ?
C4 C5 C6 121.31(16) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_pmi
_database_code_depnum_ccdc_archive 'CCDC 1039374'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N3 O3'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6306(9)
_cell_length_b                   10.7523(12)
_cell_length_c                   11.2579(13)
_cell_angle_alpha                98.521(5)
_cell_angle_beta                 97.359(5)
_cell_angle_gamma                107.517(4)
_cell_volume                     968.62(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       niddle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   ?
_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            12814
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         30.54
_reflns_number_total             5637
_reflns_number_gt                4286
_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 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)+(0.1593P)²+5.0988P] 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     SHELXL
_refine_ls_extinction_coef       0.025(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5637
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.1194
_refine_ls_wR_factor_ref         0.4097
_refine_ls_wR_factor_gt          0.4014
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.161
_refine_ls_shift/su_mean         0.010

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 0.4003(5) 0.3259(4) 0.4199(4) 0.0543(12) Uani 1 1 d . . .
O2 O 0.7238(5) 0.2027(4) 0.4508(3) 0.0503(10) Uani 1 1 d . . .
O3 O 0.3409(4) 0.0377(3) 0.0771(3) 0.0356(8) Uani 1 1 d . . .
N1 N 0.2389(5) 0.1904(4) -0.0135(4) 0.0344(8) Uani 1 1 d . . .
N2 N 0.2638(5) 0.3253(4) 0.0083(4) 0.0395(9) Uani 1 1 d . . .
N3 N 0.6613(5) 0.4648(4) 0.4221(4) 0.0421(10) Uani 1 1 d . . .
H3 H 0.6692 0.5240 0.4851 0.050 Uiso 1 1 calc R . .
C1 C -0.0879(7) -0.0470(6) -0.3320(5) 0.0488(13) Uani 1 1 d . . .
H1 H -0.1610 -0.0987 -0.4023 0.059 Uiso 1 1 calc R . .
C2 C -0.0342(7) 0.0897(6) -0.3155(5) 0.0502(14) Uani 1 1 d . . .
H2 H -0.0696 0.1301 -0.3763 0.060 Uiso 1 1 calc R . .
C3 C 0.0717(7) 0.1681(5) -0.2098(5) 0.0439(12) Uani 1 1 d . . .
H3A H 0.1047 0.2603 -0.1990 0.053 Uiso 1 1 calc R . .
C4 C 0.1278(6) 0.1081(5) -0.1207(4) 0.0333(9) Uani 1 1 d . . .
C5 C 0.3401(5) 0.1628(4) 0.0736(4) 0.0300(8) Uani 1 1 d . . .
C6 C 0.4321(5) 0.2768(4) 0.1538(4) 0.0306(9) Uani 1 1 d . . .
C7 C 0.5567(5) 0.2788(4) 0.2598(4) 0.0298(8) Uani 1 1 d . . .
C8 C 0.7309(5) 0.3627(4) 0.2545(4) 0.0316(9) Uani 1 1 d . . .
C9 C 0.7856(6) 0.4702(4) 0.3524(4) 0.0351(10) Uani 1 1 d . . .
C10 C 0.9418(6) 0.5631(5) 0.3721(6) 0.0460(13) Uani 1 1 d . . .
H10 H 0.9783 0.6333 0.4391 0.055 Uiso 1 1 calc R . .
C11 C 1.0407(7) 0.5474(6) 0.2887(7) 0.0551(15) Uani 1 1 d . . .
H11 H 1.1467 0.6081 0.3003 0.066 Uiso 1 1 calc R . .
C12 C 0.3788(6) 0.3759(5) 0.1079(5) 0.0364(10) Uani 1 1 d . . .
C13 C 0.4363(8) 0.5222(5) 0.1608(6) 0.0534(14) Uani 1 1 d . . .
H13A H 0.3795 0.5656 0.1107 0.080 Uiso 1 1 calc R . .
H13B H 0.5531 0.5587 0.1636 0.080 Uiso 1 1 calc R . .
H13C H 0.4131 0.5358 0.2420 0.080 Uiso 1 1 calc R . .
C14 C 0.5267(6) 0.3548(4) 0.3782(4) 0.0367(10) Uani 1 1 d . . .
C15 C 0.8303(7) 0.3500(5) 0.1707(5) 0.0417(11) Uani 1 1 d . . .
H15 H 0.7935 0.2799 0.1036 0.050 Uiso 1 1 calc R . .
C16 C 0.9876(7) 0.4441(6) 0.1879(7) 0.0548(15) Uani 1 1 d . . .
H16 H 1.0565 0.4374 0.1318 0.066 Uiso 1 1 calc R . .
C17 C 0.5377(5) 0.1338(4) 0.2653(4) 0.0303(8) Uani 1 1 d . . .
C18 C 0.6370(6) 0.1088(5) 0.3708(4) 0.0351(9) Uani 1 1 d . . .
C19 C 0.6328(7) -0.0311(5) 0.3749(5) 0.0442(12) Uani 1 1 d . . .
H19A H 0.6530 -0.0401 0.4594 0.053 Uiso 1 1 calc R . .
H19B H 0.7207 -0.0486 0.3368 0.053 Uiso 1 1 calc R . .
C20 C 0.4676(7) -0.1342(5) 0.3099(5) 0.0418(11) Uani 1 1 d . . .
H20A H 0.4753 -0.2228 0.3061 0.050 Uiso 1 1 calc R . .
H20B H 0.3820 -0.1270 0.3560 0.050 Uiso 1 1 calc R . .
C21 C 0.4216(7) -0.1134(4) 0.1820(4) 0.0380(10) Uani 1 1 d . . .
H21A H 0.4921 -0.1413 0.1307 0.046 Uiso 1 1 calc R . .
H21B H 0.3082 -0.1684 0.1484 0.046 Uiso 1 1 calc R . .
C22 C 0.4389(6) 0.0279(4) 0.1799(4) 0.0303(8) Uani 1 1 d . . .
C23 C 0.0757(6) -0.0297(5) -0.1356(5) 0.0390(10) Uani 1 1 d . . .
H23 H 0.1117 -0.0704 -0.0753 0.047 Uiso 1 1 calc R . .
C24 C -0.0316(7) -0.1058(5) -0.2426(5) 0.0450(12) Uani 1 1 d . . .
H24 H -0.0658 -0.1981 -0.2539 0.054 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 C14 1.215(6) . ?
O2 C18 1.222(6) . ?
O3 C5 1.353(5) . ?
O3 C22 1.381(5) . ?
N1 C5 1.355(6) . ?
N1 N2 1.380(5) . ?
N1 C4 1.426(6) . ?
N2 C12 1.321(7) . ?
N3 C14 1.359(6) . ?
N3 C9 1.401(6) . ?
N3 H3 0.8600 . ?
C1 C24 1.377(8) . ?
C1 C2 1.377(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(7) . ?
C3 H3A 0.9300 . ?
C4 C23 1.390(7) . ?
C5 C6 1.361(6) . ?
C6 C12 1.419(6) . ?
C6 C7 1.493(6) . ?
C7 C8 1.516(6) . ?
C7 C17 1.530(6) . ?
C7 C14 1.551(6) . ?
C8 C15 1.373(7) . ?
C8 C9 1.391(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.372(9) . ?
C10 H10 0.9300 . ?
C11 C16 1.385(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.501(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.397(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.353(6) . ?
C17 C18 1.479(6) . ?
C18 C19 1.502(7) . ?
C19 C20 1.529(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.511(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.485(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 C24 1.395(7) . ?
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
C5 O3 C22 114.1(3) . . ?
C5 N1 N2 109.3(4) . . ?
C5 N1 C4 131.5(4) . . ?
N2 N1 C4 119.0(4) . . ?
C12 N2 N1 105.5(4) . . ?
C14 N3 C9 111.8(4) . . ?
C14 N3 H3 124.1 . . ?
C9 N3 H3 124.1 . . ?
C24 C1 C2 118.9(5) . . ?
C24 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C1 C2 C3 121.1(5) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C23 120.3(5) . . ?
C3 C4 N1 118.7(4) . . ?
C23 C4 N1 121.0(4) . . ?
N1 C5 C6 109.8(4) . . ?
N1 C5 O3 122.7(4) . . ?
C6 C5 O3 127.5(4) . . ?
C5 C6 C12 103.3(4) . . ?
C5 C6 C7 122.5(4) . . ?
C12 C6 C7 134.1(4) . . ?
C6 C7 C8 112.9(4) . . ?
C6 C7 C17 106.8(3) . . ?
C8 C7 C17 113.9(4) . . ?
C6 C7 C14 109.5(4) . . ?
C8 C7 C14 101.3(3) . . ?
C17 C7 C14 112.3(4) . . ?
C15 C8 C9 119.9(4) . . ?
C15 C8 C7 131.0(4) . . ?
C9 C8 C7 109.1(4) . . ?
C10 C9 C8 122.0(5) . . ?
C10 C9 N3 128.4(5) . . ?
C8 C9 N3 109.6(4) . . ?
C11 C10 C9 117.2(5) . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C10 C11 C16 122.1(5) . . ?
C10 C11 H11 118.9 . . ?
C16 C11 H11 118.9 . . ?
N2 C12 C6 112.0(4) . . ?
N2 C12 C13 120.6(5) . . ?
C6 C12 C13 127.4(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N3 125.8(4) . . ?
O1 C14 C7 125.9(4) . . ?
N3 C14 C7 108.1(4) . . ?
C8 C15 C16 118.9(5) . . ?
C8 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 119.8(6) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C22 C17 C18 118.2(4) . . ?
C22 C17 C7 124.6(4) . . ?
C18 C17 C7 117.3(4) . . ?
O2 C18 C17 119.3(4) . . ?
O2 C18 C19 121.6(5) . . ?
C17 C18 C19 119.1(4) . . ?
C18 C19 C20 112.5(4) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 110.9(4) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C22 C21 C20 111.9(4) . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C17 C22 O3 123.9(4) . . ?
C17 C22 C21 125.5(4) . . ?
O3 C22 C21 110.7(4) . . ?
C4 C23 C24 118.8(5) . . ?
C4 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C1 C24 C23 121.3(5) . . ?
C1 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.112
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.063
;
####################################################################### 
# 
# 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_ard_pm_phdim_0m
_database_code_depnum_ccdc_archive 'CCDC 1410076'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8170(8)
_cell_length_b                   9.4031(10)
_cell_length_c                   16.4402(17)
_cell_angle_alpha                73.821(3)
_cell_angle_beta                 81.557(3)
_cell_angle_gamma                69.541(3)
_cell_volume                     1085.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  0.9859
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12030
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         24.55
_reflns_number_total             3599
_reflns_number_gt                2664
_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    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'

_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)+(0.0400P)²+0.3000P] 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     SHELXL
_refine_ls_extinction_coef       0.0099(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.8520(3) 0.5455(2) 0.11125(11) 0.0432(5) Uani 1 1 d . . .
C2 C 0.8624(2) 0.4635(2) 0.19555(11) 0.0376(4) Uani 1 1 d . . .
C3 C 0.7488(3) 0.3752(2) 0.20411(12) 0.0420(5) Uani 1 1 d . . .
C4 C 0.6933(3) 0.2658(3) 0.27878(13) 0.0562(6) Uani 1 1 d . . .
H4A H 0.6204 0.2174 0.2610 0.084 Uiso 1 1 calc R . .
H4B H 0.6233 0.3226 0.3195 0.084 Uiso 1 1 calc R . .
H4C H 0.8004 0.1866 0.3040 0.084 Uiso 1 1 calc R . .
C5 C 0.9685(2) 0.4879(2) 0.25715(10) 0.0351(4) Uani 1 1 d . . .
C6 C 1.1030(3) 0.3293(2) 0.30016(11) 0.0380(4) Uani 1 1 d . . .
C7 C 1.0807(3) 0.2656(2) 0.39245(11) 0.0410(5) Uani 1 1 d . . .
C8 C 1.2027(3) 0.1212(3) 0.42864(13) 0.0648(7) Uani 1 1 d . . .
H8 H 1.2942 0.0678 0.3946 0.078 Uiso 1 1 calc R . .
C9 C 1.1900(4) 0.0559(3) 0.51437(14) 0.0830(9) Uani 1 1 d . . .
H9 H 1.2725 -0.0410 0.5384 0.100 Uiso 1 1 calc R . .
C10 C 1.0545(4) 0.1354(3) 0.56404(13) 0.0720(8) Uani 1 1 d . . .
H10 H 1.0448 0.0912 0.6220 0.086 Uiso 1 1 calc R . .
C11 C 0.9334(3) 0.2782(3) 0.52982(12) 0.0537(6) Uani 1 1 d . . .
H11 H 0.8424 0.3297 0.5648 0.064 Uiso 1 1 calc R . .
C12 C 0.9440(3) 0.3485(2) 0.44302(11) 0.0395(5) Uani 1 1 d . . .
C13 C 0.8195(2) 0.5057(2) 0.40577(11) 0.0393(5) Uani 1 1 d . . .
C14 C 0.6862(3) 0.5911(3) 0.45633(13) 0.0583(6) Uani 1 1 d . . .
H14 H 0.6741 0.5469 0.5141 0.070 Uiso 1 1 calc R . .
C15 C 0.5731(3) 0.7387(3) 0.42231(15) 0.0716(7) Uani 1 1 d . . .
H15 H 0.4845 0.7929 0.4570 0.086 Uiso 1 1 calc R . .
C16 C 0.5896(3) 0.8080(3) 0.33647(15) 0.0617(6) Uani 1 1 d . . .
H16 H 0.5141 0.9088 0.3134 0.074 Uiso 1 1 calc R . .
C17 C 0.7195(3) 0.7250(2) 0.28640(12) 0.0454(5) Uani 1 1 d . . .
H17 H 0.7312 0.7706 0.2288 0.055 Uiso 1 1 calc R . .
C18 C 0.8343(2) 0.5744(2) 0.31931(11) 0.0361(4) Uani 1 1 d . . .
C19 C 1.0785(2) 0.5908(2) 0.20386(11) 0.0360(4) Uani 1 1 d . . .
C20 C 1.2161(2) 0.6099(2) 0.24760(12) 0.0413(5) Uani 1 1 d . . .
C21 C 1.3201(3) 0.7181(3) 0.20055(14) 0.0572(6) Uani 1 1 d . . .
H21A H 1.4342 0.6572 0.1768 0.069 Uiso 1 1 calc R . .
H21B H 1.3502 0.7632 0.2407 0.069 Uiso 1 1 calc R . .
C22 C 1.2188(3) 0.8510(2) 0.12909(13) 0.0513(5) Uani 1 1 d . . .
C23 C 1.0583(3) 0.9675(3) 0.16660(15) 0.0663(7) Uani 1 1 d . . .
H23A H 0.9946 1.0506 0.1215 0.099 Uiso 1 1 calc R . .
H23B H 1.1035 1.0102 0.2023 0.099 Uiso 1 1 calc R . .
H23C H 0.9762 0.9147 0.1995 0.099 Uiso 1 1 calc R . .
C24 C 1.3486(4) 0.9363(3) 0.07636(17) 0.0775(8) Uani 1 1 d . . .
H24A H 1.4520 0.8630 0.0544 0.116 Uiso 1 1 calc R . .
H24B H 1.3899 0.9828 0.1115 0.116 Uiso 1 1 calc R . .
H24C H 1.2855 1.0167 0.0301 0.116 Uiso 1 1 calc R . .
C25 C 1.1527(3) 0.7779(3) 0.07315(12) 0.0540(6) Uani 1 1 d . . .
H25A H 1.0713 0.8607 0.0328 0.065 Uiso 1 1 calc R . .
H25B H 1.2571 0.7227 0.0412 0.065 Uiso 1 1 calc R . .
C26 C 1.0555(3) 0.6670(2) 0.12174(11) 0.0423(5) Uani 1 1 d . . .
H1N H 0.588(2) 0.374(3) 0.1133(14) 0.078(7) Uiso 1 1 d D . .
H4WA H 0.361(4) 0.365(3) 0.0473(14) 0.116(12) Uiso 1 1 d D . .
H4WB H 0.338(4) 0.301(4) 0.1353(15) 0.124(13) Uiso 1 1 d D . .
N1 N 0.6835(2) 0.4085(2) 0.12705(10) 0.0504(5) Uani 1 1 d D . .
N2 N 0.7446(2) 0.5168(2) 0.06776(10) 0.0534(5) Uani 1 1 d . . .
O1 O 0.93839(19) 0.65354(17) 0.07221(8) 0.0528(4) Uani 1 1 d . . .
O2 O 1.22119(19) 0.25556(16) 0.25625(8) 0.0511(4) Uani 1 1 d . . .
O3 O 1.24776(18) 0.53461(17) 0.32073(8) 0.0524(4) Uani 1 1 d . . .
O4 O 0.4118(2) 0.3122(2) 0.09296(11) 0.0627(5) Uani 1 1 d D . .


_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
C1 N2 1.316(2) . ?
C1 O1 1.374(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.383(3) . ?
C2 C5 1.509(2) . ?
C3 N1 1.349(2) . ?
C3 C4 1.485(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C19 1.526(2) . ?
C5 C18 1.536(2) . ?
C5 C6 1.537(3) . ?
C6 O2 1.221(2) . ?
C6 C7 1.477(2) . ?
C7 C8 1.385(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.474(3) . ?
C13 C18 1.394(2) . ?
C13 C14 1.398(3) . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C19 C26 1.346(2) . ?
C19 C20 1.463(2) . ?
C20 O3 1.224(2) . ?
C20 C21 1.500(3) . ?
C21 C22 1.527(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C25 1.525(3) . ?
C22 C23 1.530(3) . ?
C22 C24 1.533(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.488(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O1 1.369(2) . ?
N1 N2 1.366(2) . ?
N1 H1N 0.987(10) . ?
O4 H4WA 0.842(17) . ?
O4 H4WB 0.843(18) . ?

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
N2 C1 O1 119.48(16) . . ?
N2 C1 C2 114.75(18) . . ?
O1 C1 C2 125.74(16) . . ?
C3 C2 C1 103.57(16) . . ?
C3 C2 C5 133.54(16) . . ?
C1 C2 C5 122.74(17) . . ?
N1 C3 C2 106.38(17) . . ?
N1 C3 C4 121.97(18) . . ?
C2 C3 C4 131.63(17) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 C19 106.01(14) . . ?
C2 C5 C18 109.29(14) . . ?
C19 C5 C18 109.44(15) . . ?
C2 C5 C6 109.25(15) . . ?
C19 C5 C6 108.46(14) . . ?
C18 C5 C6 114.07(14) . . ?
O2 C6 C7 121.43(17) . . ?
O2 C6 C5 118.87(16) . . ?
C7 C6 C5 119.62(16) . . ?
C8 C7 C12 120.31(18) . . ?
C8 C7 C6 117.91(18) . . ?
C12 C7 C6 121.77(17) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 117.58(18) . . ?
C11 C12 C13 121.72(17) . . ?
C7 C12 C13 120.68(16) . . ?
C18 C13 C14 118.25(19) . . ?
C18 C13 C12 120.74(16) . . ?
C14 C13 C12 120.99(17) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 121.81(19) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C13 119.53(17) . . ?
C17 C18 C5 117.80(16) . . ?
C13 C18 C5 122.62(16) . . ?
C26 C19 C20 118.30(17) . . ?
C26 C19 C5 125.40(16) . . ?
C20 C19 C5 116.28(15) . . ?
O3 C20 C19 119.67(18) . . ?
O3 C20 C21 121.29(18) . . ?
C19 C20 C21 119.01(17) . . ?
C20 C21 C22 114.67(17) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C25 C22 C21 107.40(18) . . ?
C25 C22 C23 111.22(18) . . ?
C21 C22 C23 109.69(18) . . ?
C25 C22 C24 109.46(18) . . ?
C21 C22 C24 109.96(18) . . ?
C23 C22 C24 109.09(19) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 113.42(16) . . ?
C26 C25 H25A 108.9 . . ?
C22 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C22 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C19 C26 O1 124.38(18) . . ?
C19 C26 C25 124.44(18) . . ?
O1 C26 C25 111.19(16) . . ?
C3 N1 N2 112.99(16) . . ?
C3 N1 H1N 126.5(14) . . ?
N2 N1 H1N 119.9(14) . . ?
C1 N2 N1 102.30(15) . . ?
C26 O1 C1 114.53(14) . . ?
H4WA O4 H4WB 114(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.55
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033
