# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 1045919'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_weight         317.34

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   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2169(8)
_cell_length_b                   9.6220(9)
_cell_length_c                   11.5715(11)
_cell_angle_alpha                65.807(2)
_cell_angle_beta                 72.714(2)
_cell_angle_gamma                89.496(2)
_cell_volume                     790.10(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1733
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.11

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_T_max  0.9678
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4257
_diffrn_reflns_av_R_equivalents  0.0097
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3041
_reflns_number_gt                2142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.1548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3041
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.1146(2) 0.61685(19) 0.70076(16) 0.0459(4) Uani 1 1 d . . .
H1A H 0.0780 0.7014 0.6434 0.055 Uiso 1 1 calc R . .
C2 C 0.1227(2) 0.4863(2) 0.68264(18) 0.0562(5) Uani 1 1 d . . .
H2A H 0.0918 0.4824 0.6129 0.067 Uiso 1 1 calc R . .
C3 C 0.1772(3) 0.3568(2) 0.76777(19) 0.0612(5) Uani 1 1 d . . .
H3A H 0.1815 0.2679 0.7541 0.073 Uiso 1 1 calc R . .
C4 C 0.2233(2) 0.35995(19) 0.86912(18) 0.0551(5) Uani 1 1 d . . .
H4A H 0.2591 0.2731 0.9246 0.066 Uiso 1 1 calc R . .
C5 C 0.2182(2) 0.49428(17) 0.89272(15) 0.0420(4) Uani 1 1 d . . .
C6 C 0.16146(18) 0.62631(17) 0.80674(14) 0.0373(3) Uani 1 1 d . . .
C7 C 0.15836(18) 0.76006(17) 0.82869(15) 0.0366(3) Uani 1 1 d . . .
C8 C 0.20755(18) 0.76534(17) 0.93323(15) 0.0379(3) Uani 1 1 d . . .
C9 C 0.2629(2) 0.63163(18) 1.01848(16) 0.0432(4) Uani 1 1 d . . .
C10 C 0.2665(2) 0.50078(18) 0.99590(16) 0.0479(4) Uani 1 1 d . . .
H10A H 0.3024 0.4143 1.0517 0.057 Uiso 1 1 calc R . .
C11 C 0.3129(2) 0.6379(2) 1.12460(18) 0.0585(5) Uani 1 1 d . . .
H11A H 0.3493 0.5518 1.1805 0.070 Uiso 1 1 calc R . .
C12 C 0.3084(3) 0.7657(2) 1.1452(2) 0.0670(5) Uani 1 1 d . . .
H12A H 0.3425 0.7677 1.2144 0.080 Uiso 1 1 calc R . .
C13 C 0.2523(3) 0.8967(2) 1.06247(19) 0.0599(5) Uani 1 1 d . . .
H13A H 0.2491 0.9844 1.0778 0.072 Uiso 1 1 calc R . .
C14 C 0.2028(2) 0.89671(19) 0.96076(17) 0.0482(4) Uani 1 1 d . . .
H14A H 0.1650 0.9842 0.9080 0.058 Uiso 1 1 calc R . .
C15 C 0.10633(19) 0.89989(17) 0.73605(15) 0.0365(3) Uani 1 1 d . . .
C16 C -0.0923(2) 1.02243(18) 0.65111(15) 0.0409(4) Uani 1 1 d . . .
C17 C 0.1736(2) 1.13847(18) 0.57298(15) 0.0431(4) Uani 1 1 d . . .
C18 C -0.3786(2) 0.9011(2) 0.7343(2) 0.0621(5) Uani 1 1 d . . .
H18A H -0.4866 0.9221 0.7190 0.093 Uiso 1 1 calc R . .
H18B H -0.3902 0.8817 0.8248 0.093 Uiso 1 1 calc R . .
H18C H -0.3443 0.8125 0.7195 0.093 Uiso 1 1 calc R . .
C19 C 0.4581(3) 1.2678(2) 0.4890(2) 0.0765(6) Uani 1 1 d . . .
H19A H 0.5224 1.3654 0.4236 0.115 Uiso 1 1 calc R . .
H19B H 0.5091 1.1874 0.4679 0.115 Uiso 1 1 calc R . .
H19C H 0.4594 1.2525 0.5760 0.115 Uiso 1 1 calc R . .
N1 N -0.05848(16) 0.89530(14) 0.74047(12) 0.0398(3) Uani 1 1 d . . .
N2 N 0.22835(16) 1.01933(14) 0.65444(13) 0.0425(3) Uani 1 1 d . . .
N3 N 0.01666(17) 1.14806(15) 0.56446(13) 0.0477(3) Uani 1 1 d . . .
O1 O -0.25070(14) 1.03101(14) 0.64383(12) 0.0545(3) Uani 1 1 d . . .
O2 O 0.28358(16) 1.26512(13) 0.48802(12) 0.0599(4) 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 C2 1.353(2) . ?
C1 C6 1.426(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.404(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.347(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.424(2) . ?
C4 H4A 0.9300 . ?
C5 C10 1.389(2) . ?
C5 C6 1.432(2) . ?
C6 C7 1.409(2) . ?
C7 C8 1.404(2) . ?
C7 C15 1.491(2) . ?
C8 C14 1.422(2) . ?
C8 C9 1.432(2) . ?
C9 C10 1.385(2) . ?
C9 C11 1.429(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.344(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.408(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.354(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 N2 1.3364(19) . ?
C15 N1 1.3403(19) . ?
C16 N3 1.327(2) . ?
C16 O1 1.3283(18) . ?
C16 N1 1.3309(19) . ?
C17 N3 1.322(2) . ?
C17 N2 1.3276(19) . ?
C17 O2 1.3334(19) . ?
C18 O1 1.435(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O2 1.438(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.81(16) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 120.87(17) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 120.64(16) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.03(16) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C10 C5 C4 122.11(15) . . ?
C10 C5 C6 119.37(14) . . ?
C4 C5 C6 118.52(15) . . ?
C7 C6 C1 123.17(14) . . ?
C7 C6 C5 118.68(13) . . ?
C1 C6 C5 118.13(14) . . ?
C8 C7 C6 121.44(13) . . ?
C8 C7 C15 119.63(13) . . ?
C6 C7 C15 118.91(13) . . ?
C7 C8 C14 123.28(14) . . ?
C7 C8 C9 118.92(13) . . ?
C14 C8 C9 117.80(14) . . ?
C10 C9 C11 122.06(15) . . ?
C10 C9 C8 119.33(14) . . ?
C11 C9 C8 118.61(15) . . ?
C9 C10 C5 122.25(14) . . ?
C9 C10 H10A 118.9 . . ?
C5 C10 H10A 118.9 . . ?
C12 C11 C9 121.28(17) . . ?
C12 C11 H11A 119.4 . . ?
C9 C11 H11A 119.4 . . ?
C11 C12 C13 120.18(17) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C14 C13 C12 120.94(17) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C8 121.17(16) . . ?
C13 C14 H14A 119.4 . . ?
C8 C14 H14A 119.4 . . ?
N2 C15 N1 125.28(14) . . ?
N2 C15 C7 117.26(13) . . ?
N1 C15 C7 117.46(13) . . ?
N3 C16 O1 113.57(14) . . ?
N3 C16 N1 127.11(14) . . ?
O1 C16 N1 119.31(14) . . ?
N3 C17 N2 127.09(15) . . ?
N3 C17 O2 113.59(14) . . ?
N2 C17 O2 119.32(14) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 N1 C15 113.51(13) . . ?
C17 N2 C15 113.93(13) . . ?
C17 N3 C16 113.04(13) . . ?
C16 O1 C18 117.81(13) . . ?
C17 O2 C19 118.39(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C10 -179.48(16) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C2 C1 C6 C7 178.83(15) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C10 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C6 C7 -179.19(14) . . . . ?
C10 C5 C6 C1 179.32(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C1 C6 C7 C8 -179.20(14) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C1 C6 C7 C15 -1.0(2) . . . . ?
C5 C6 C7 C15 177.49(13) . . . . ?
C6 C7 C8 C14 -178.57(14) . . . . ?
C15 C7 C8 C14 3.2(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C15 C7 C8 C9 -177.84(13) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C14 C8 C9 C10 178.95(14) . . . . ?
C7 C8 C9 C11 179.94(15) . . . . ?
C14 C8 C9 C11 -1.1(2) . . . . ?
C11 C9 C10 C5 -179.88(16) . . . . ?
C8 C9 C10 C5 0.1(2) . . . . ?
C4 C5 C10 C9 179.49(15) . . . . ?
C6 C5 C10 C9 -0.5(2) . . . . ?
C10 C9 C11 C12 -179.88(18) . . . . ?
C8 C9 C11 C12 0.1(3) . . . . ?
C9 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C8 -0.7(3) . . . . ?
C7 C8 C14 C13 -179.70(16) . . . . ?
C9 C8 C14 C13 1.3(2) . . . . ?
C8 C7 C15 N2 67.80(18) . . . . ?
C6 C7 C15 N2 -110.46(15) . . . . ?
C8 C7 C15 N1 -112.74(15) . . . . ?
C6 C7 C15 N1 69.00(18) . . . . ?
N3 C16 N1 C15 -1.5(2) . . . . ?
O1 C16 N1 C15 178.80(13) . . . . ?
N2 C15 N1 C16 1.9(2) . . . . ?
C7 C15 N1 C16 -177.56(13) . . . . ?
N3 C17 N2 C15 -1.1(2) . . . . ?
O2 C17 N2 C15 179.21(13) . . . . ?
N1 C15 N2 C17 -0.7(2) . . . . ?
C7 C15 N2 C17 178.69(13) . . . . ?
N2 C17 N3 C16 1.4(2) . . . . ?
O2 C17 N3 C16 -178.86(13) . . . . ?
O1 C16 N3 C17 179.74(13) . . . . ?
N1 C16 N3 C17 0.0(2) . . . . ?
N3 C16 O1 C18 -179.58(14) . . . . ?
N1 C16 O1 C18 0.2(2) . . . . ?
N3 C17 O2 C19 179.73(15) . . . . ?
N2 C17 O2 C19 -0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1045920'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H21 N3 O'
_chemical_formula_weight         463.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.930(3)
_cell_length_b                   17.081(7)
_cell_length_c                   18.143(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.463(15)
_cell_angle_gamma                90.00
_cell_volume                     2379.6(15)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11990
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4235
_reflns_number_gt                2271
_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)+(0.0467P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4235
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6817(2) 0.89757(10) 0.85060(9) 0.0533(5) Uani 1 1 d . . .
N1 N 0.8713(2) 0.84973(11) 0.95857(10) 0.0397(5) Uani 1 1 d . . .
N2 N 0.8594(2) 0.71264(11) 0.98197(10) 0.0433(5) Uani 1 1 d . . .
N3 N 0.6610(2) 0.76999(12) 0.87489(11) 0.0458(5) Uani 1 1 d . . .
C1 C 0.4986(3) 0.60811(15) 0.92355(14) 0.0492(7) Uani 1 1 d . . .
C2 C 0.4309(4) 0.65405(16) 0.97544(16) 0.0604(8) Uani 1 1 d . . .
H2A H 0.4819 0.7021 0.9917 0.073 Uiso 1 1 calc R . .
C3 C 0.2938(4) 0.62904(19) 1.00162(19) 0.0772(10) Uani 1 1 d . . .
H3A H 0.2528 0.6599 1.0356 0.093 Uiso 1 1 calc R . .
C4 C 0.2133(4) 0.5566(2) 0.9777(2) 0.0832(11) Uani 1 1 d . . .
H4A H 0.1197 0.5401 0.9960 0.100 Uiso 1 1 calc R . .
C5 C 0.2717(4) 0.5109(2) 0.9278(2) 0.0809(11) Uani 1 1 d . . .
H5A H 0.2169 0.4634 0.9124 0.097 Uiso 1 1 calc R . .
C6 C 0.4155(4) 0.53446(17) 0.89872(17) 0.0606(8) Uani 1 1 d . . .
C7 C 0.4809(4) 0.48855(17) 0.84826(18) 0.0712(10) Uani 1 1 d . . .
H7A H 0.4255 0.4416 0.8313 0.085 Uiso 1 1 calc R . .
C8 C 0.6253(4) 0.51015(17) 0.82233(16) 0.0625(8) Uani 1 1 d . . .
C9 C 0.7092(3) 0.58325(14) 0.84752(14) 0.0491(7) Uani 1 1 d . . .
C10 C 0.6428(3) 0.63146(14) 0.89714(14) 0.0450(7) Uani 1 1 d . . .
C11 C 0.8575(4) 0.60392(16) 0.82088(15) 0.0595(8) Uani 1 1 d . . .
H11A H 0.9147 0.6508 0.8368 0.071 Uiso 1 1 calc R . .
C12 C 0.9178(4) 0.55650(19) 0.77246(17) 0.0739(9) Uani 1 1 d . . .
H12A H 1.0146 0.5714 0.7556 0.089 Uiso 1 1 calc R . .
C13 C 0.8341(5) 0.4854(2) 0.7481(2) 0.0888(11) Uani 1 1 d . . .
H13A H 0.8762 0.4538 0.7150 0.107 Uiso 1 1 calc R . .
C14 C 0.6935(5) 0.46182(19) 0.77182(19) 0.0814(11) Uani 1 1 d . . .
H14A H 0.6408 0.4141 0.7553 0.098 Uiso 1 1 calc R . .
C15 C 0.7259(3) 0.70911(14) 0.91936(13) 0.0404(6) Uani 1 1 d . . .
C16 C 0.7421(3) 0.83779(14) 0.89718(13) 0.0394(6) Uani 1 1 d . . .
C17 C 0.9263(3) 0.78417(14) 0.99937(12) 0.0374(6) Uani 1 1 d . . .
C18 C 0.7628(4) 0.97320(15) 0.86860(17) 0.0676(8) Uani 1 1 d . . .
H18A H 0.7139 1.0095 0.8286 0.101 Uiso 1 1 calc R . .
H18B H 0.8858 0.9686 0.8736 0.101 Uiso 1 1 calc R . .
H18C H 0.7427 0.9918 0.9156 0.101 Uiso 1 1 calc R . .
C19 C 1.0745(3) 0.79277(13) 1.06874(12) 0.0373(6) Uani 1 1 d . . .
C20 C 1.0560(3) 0.76325(14) 1.13932(13) 0.0402(6) Uani 1 1 d . . .
C21 C 1.2020(3) 0.76838(14) 1.20477(13) 0.0434(6) Uani 1 1 d . . .
C22 C 1.3574(3) 0.80101(15) 1.19720(14) 0.0505(7) Uani 1 1 d . . .
H22A H 1.4515 0.8031 1.2397 0.061 Uiso 1 1 calc R . .
C23 C 1.3777(3) 0.83074(14) 1.12825(14) 0.0440(7) Uani 1 1 d . . .
C24 C 1.2330(3) 0.82776(13) 1.06199(13) 0.0405(6) Uani 1 1 d . . .
C25 C 1.2617(3) 0.85877(15) 0.99300(14) 0.0507(7) Uani 1 1 d . . .
H25A H 1.1715 0.8571 0.9490 0.061 Uiso 1 1 calc R . .
C26 C 1.4169(3) 0.89070(16) 0.98966(16) 0.0573(7) Uani 1 1 d . . .
H26A H 1.4308 0.9104 0.9438 0.069 Uiso 1 1 calc R . .
C27 C 1.5573(3) 0.89419(17) 1.05548(18) 0.0626(8) Uani 1 1 d . . .
H27A H 1.6627 0.9165 1.0529 0.075 Uiso 1 1 calc R . .
C28 C 1.5377(3) 0.86502(16) 1.12215(17) 0.0577(8) Uani 1 1 d . . .
H28A H 1.6308 0.8674 1.1650 0.069 Uiso 1 1 calc R . .
C29 C 1.1829(4) 0.74068(16) 1.27659(14) 0.0551(7) Uani 1 1 d . . .
H29A H 1.2771 0.7432 1.3190 0.066 Uiso 1 1 calc R . .
C30 C 1.0303(4) 0.71094(16) 1.28371(14) 0.0593(8) Uani 1 1 d . . .
H30A H 1.0201 0.6935 1.3310 0.071 Uiso 1 1 calc R . .
C31 C 0.8853(3) 0.70595(15) 1.21983(14) 0.0552(7) Uani 1 1 d . . .
H31A H 0.7805 0.6856 1.2256 0.066 Uiso 1 1 calc R . .
C32 C 0.8982(3) 0.73068(15) 1.15026(14) 0.0494(7) Uani 1 1 d . . .
H32A H 0.8021 0.7263 1.1088 0.059 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 C16 1.336(3) . ?
O1 C18 1.444(3) . ?
N1 C16 1.328(3) . ?
N1 C17 1.353(3) . ?
N2 C17 1.338(3) . ?
N2 C15 1.347(3) . ?
N3 C16 1.337(3) . ?
N3 C15 1.338(3) . ?
C1 C10 1.404(4) . ?
C1 C2 1.429(4) . ?
C1 C6 1.439(4) . ?
C2 C3 1.360(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.410(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.360(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.429(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.400(4) . ?
C7 C8 1.392(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.435(4) . ?
C8 C14 1.435(4) . ?
C9 C10 1.415(3) . ?
C9 C11 1.423(4) . ?
C10 C15 1.491(3) . ?
C11 C12 1.366(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.401(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.353(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C17 C19 1.500(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.418(3) . ?
C19 C24 1.424(3) . ?
C20 C32 1.428(3) . ?
C20 C21 1.439(3) . ?
C21 C22 1.391(4) . ?
C21 C29 1.429(3) . ?
C22 C23 1.396(3) . ?
C22 H22A 0.9300 . ?
C23 C28 1.427(3) . ?
C23 C24 1.440(3) . ?
C24 C25 1.429(3) . ?
C25 C26 1.361(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.416(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.353(4) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 C30 1.348(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.417(3) . ?
C30 H30A 0.9300 . ?
C31 C32 1.359(3) . ?
C31 H31A 0.9300 . ?
C32 H32A 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
C16 O1 C18 118.15(19) . . ?
C16 N1 C17 114.1(2) . . ?
C17 N2 C15 114.9(2) . . ?
C16 N3 C15 114.05(19) . . ?
C10 C1 C2 122.7(2) . . ?
C10 C1 C6 119.3(3) . . ?
C2 C1 C6 117.9(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C7 C6 C5 123.0(3) . . ?
C7 C6 C1 118.6(3) . . ?
C5 C6 C1 118.4(3) . . ?
C8 C7 C6 122.9(3) . . ?
C8 C7 H7A 118.6 . . ?
C6 C7 H7A 118.6 . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 C14 122.4(3) . . ?
C9 C8 C14 119.0(3) . . ?
C10 C9 C11 122.8(2) . . ?
C10 C9 C8 119.5(3) . . ?
C11 C9 C8 117.7(3) . . ?
C1 C10 C9 121.1(2) . . ?
C1 C10 C15 120.2(2) . . ?
C9 C10 C15 118.7(2) . . ?
C12 C11 C9 121.5(3) . . ?
C12 C11 H11A 119.2 . . ?
C9 C11 H11A 119.2 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C8 120.2(3) . . ?
C13 C14 H14A 119.9 . . ?
C8 C14 H14A 119.9 . . ?
N3 C15 N2 125.2(2) . . ?
N3 C15 C10 116.83(19) . . ?
N2 C15 C10 118.0(2) . . ?
N1 C16 O1 119.6(2) . . ?
N1 C16 N3 126.8(2) . . ?
O1 C16 N3 113.7(2) . . ?
N2 C17 N1 124.9(2) . . ?
N2 C17 C19 118.0(2) . . ?
N1 C17 C19 117.1(2) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 121.3(2) . . ?
C20 C19 C17 119.1(2) . . ?
C24 C19 C17 119.5(2) . . ?
C19 C20 C32 123.8(2) . . ?
C19 C20 C21 118.7(2) . . ?
C32 C20 C21 117.5(2) . . ?
C22 C21 C29 121.4(2) . . ?
C22 C21 C20 119.5(2) . . ?
C29 C21 C20 119.1(2) . . ?
C21 C22 C23 122.5(2) . . ?
C21 C22 H22A 118.7 . . ?
C23 C22 H22A 118.7 . . ?
C22 C23 C28 121.5(2) . . ?
C22 C23 C24 119.3(2) . . ?
C28 C23 C24 119.2(2) . . ?
C19 C24 C25 124.6(2) . . ?
C19 C24 C23 118.6(2) . . ?
C25 C24 C23 116.8(2) . . ?
C26 C25 C24 122.1(2) . . ?
C26 C25 H25A 119.0 . . ?
C24 C25 H25A 119.0 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26A 119.7 . . ?
C27 C26 H26A 119.7 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27A 120.1 . . ?
C26 C27 H27A 120.1 . . ?
C27 C28 C23 121.6(3) . . ?
C27 C28 H28A 119.2 . . ?
C23 C28 H28A 119.2 . . ?
C30 C29 C21 120.9(2) . . ?
C30 C29 H29A 119.5 . . ?
C21 C29 H29A 119.5 . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30A 119.7 . . ?
C31 C30 H30A 119.7 . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C31 C32 C20 121.5(2) . . ?
C31 C32 H32A 119.3 . . ?
C20 C32 H32A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -178.3(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C10 C1 C6 C7 -0.5(4) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
C10 C1 C6 C5 178.4(2) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C5 C6 C7 C8 -177.4(2) . . . . ?
C1 C6 C7 C8 1.5(4) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C6 C7 C8 C14 178.7(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C14 C8 C9 C10 179.8(2) . . . . ?
C7 C8 C9 C11 179.5(2) . . . . ?
C14 C8 C9 C11 -0.2(4) . . . . ?
C2 C1 C10 C9 178.1(2) . . . . ?
C6 C1 C10 C9 -1.0(3) . . . . ?
C2 C1 C10 C15 -3.7(3) . . . . ?
C6 C1 C10 C15 177.2(2) . . . . ?
C11 C9 C10 C1 -178.5(2) . . . . ?
C8 C9 C10 C1 1.5(3) . . . . ?
C11 C9 C10 C15 3.3(3) . . . . ?
C8 C9 C10 C15 -176.7(2) . . . . ?
C10 C9 C11 C12 -179.4(2) . . . . ?
C8 C9 C11 C12 0.6(4) . . . . ?
C9 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C8 0.7(5) . . . . ?
C7 C8 C14 C13 179.9(3) . . . . ?
C9 C8 C14 C13 -0.4(4) . . . . ?
C16 N3 C15 N2 0.6(4) . . . . ?
C16 N3 C15 C10 -179.2(2) . . . . ?
C17 N2 C15 N3 1.1(3) . . . . ?
C17 N2 C15 C10 -179.0(2) . . . . ?
C1 C10 C15 N3 -88.3(3) . . . . ?
C9 C10 C15 N3 90.0(3) . . . . ?
C1 C10 C15 N2 91.9(3) . . . . ?
C9 C10 C15 N2 -89.9(3) . . . . ?
C17 N1 C16 O1 -177.2(2) . . . . ?
C17 N1 C16 N3 2.6(3) . . . . ?
C18 O1 C16 N1 1.1(3) . . . . ?
C18 O1 C16 N3 -178.7(2) . . . . ?
C15 N3 C16 N1 -2.6(4) . . . . ?
C15 N3 C16 O1 177.2(2) . . . . ?
C15 N2 C17 N1 -1.2(3) . . . . ?
C15 N2 C17 C19 179.5(2) . . . . ?
C16 N1 C17 N2 -0.5(3) . . . . ?
C16 N1 C17 C19 178.8(2) . . . . ?
N2 C17 C19 C20 -53.0(3) . . . . ?
N1 C17 C19 C20 127.7(2) . . . . ?
N2 C17 C19 C24 124.7(2) . . . . ?
N1 C17 C19 C24 -54.6(3) . . . . ?
C24 C19 C20 C32 177.2(2) . . . . ?
C17 C19 C20 C32 -5.1(4) . . . . ?
C24 C19 C20 C21 -0.7(3) . . . . ?
C17 C19 C20 C21 177.0(2) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C32 C20 C21 C22 -178.8(2) . . . . ?
C19 C20 C21 C29 178.3(2) . . . . ?
C32 C20 C21 C29 0.3(3) . . . . ?
C29 C21 C22 C23 -177.9(2) . . . . ?
C20 C21 C22 C23 1.2(4) . . . . ?
C21 C22 C23 C28 179.0(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C20 C19 C24 C25 180.0(2) . . . . ?
C17 C19 C24 C25 2.3(4) . . . . ?
C20 C19 C24 C23 1.8(3) . . . . ?
C17 C19 C24 C23 -175.9(2) . . . . ?
C22 C23 C24 C19 -1.4(3) . . . . ?
C28 C23 C24 C19 179.5(2) . . . . ?
C22 C23 C24 C25 -179.8(2) . . . . ?
C28 C23 C24 C25 1.1(3) . . . . ?
C19 C24 C25 C26 -179.1(2) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 0.5(4) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C22 C23 C28 C27 -179.7(3) . . . . ?
C24 C23 C28 C27 -0.6(4) . . . . ?
C22 C21 C29 C30 178.3(2) . . . . ?
C20 C21 C29 C30 -0.8(4) . . . . ?
C21 C29 C30 C31 0.5(4) . . . . ?
C29 C30 C31 C32 0.4(4) . . . . ?
C30 C31 C32 C20 -0.9(4) . . . . ?
C19 C20 C32 C31 -177.4(2) . . . . ?
C21 C20 C32 C31 0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
