# 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_expt_321
_database_code_depnum_ccdc_archive 'CCDC 1053586'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N3 O3'
_chemical_formula_sum            'C21 H21 N3 O3'
_chemical_formula_weight         363.41

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           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                   13.9952(17)
_cell_length_b                   9.1123(12)
_cell_length_c                   15.2436(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.909(9)
_cell_angle_gamma                90.00
_cell_volume                     1925.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4421
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   'Bruker 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            12212
_diffrn_reflns_av_R_equivalents  0.1768
_diffrn_reflns_av_sigmaI/netI    0.0993
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3344
_reflns_number_gt                2728
_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)+(0.0000P)²+4.0108P] 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         3344
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.1164
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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 0.1783(2) 0.1577(3) 0.2070(2) 0.0446(8) Uani 1 1 d . . .
O2 O 0.4914(2) 0.1412(4) 0.0997(3) 0.0726(12) Uani 1 1 d . . .
O3 O 0.3385(2) 0.0627(4) 0.08558(19) 0.0442(8) Uani 1 1 d . . .
N1 N 0.1647(2) 0.2683(4) 0.0704(2) 0.0347(9) Uani 1 1 d . . .
N2 N 0.5407(3) 0.3678(7) 0.2682(4) 0.099(2) Uani 1 1 d . . .
N3 N 0.0504(3) 0.7420(5) 0.2013(3) 0.0612(12) Uani 1 1 d . . .
C1 C 0.3547(4) 0.5410(6) -0.0356(4) 0.0625(15) Uani 1 1 d . . .
H1 H 0.3997 0.6016 -0.0571 0.075 Uiso 1 1 calc R . .
C2 C 0.2748(4) 0.4961(7) -0.0913(4) 0.0690(17) Uani 1 1 d . . .
H2 H 0.2663 0.5268 -0.1500 0.083 Uiso 1 1 calc R . .
C3 C 0.2066(4) 0.4060(6) -0.0615(3) 0.0574(14) Uani 1 1 d . . .
H3 H 0.1522 0.3757 -0.0992 0.069 Uiso 1 1 calc R . .
C4 C 0.2218(3) 0.3628(5) 0.0253(3) 0.0353(10) Uani 1 1 d . . .
C5 C 0.3024(3) 0.4053(5) 0.0830(3) 0.0318(10) Uani 1 1 d . . .
C6 C 0.3696(3) 0.4972(5) 0.0527(3) 0.0475(12) Uani 1 1 d . . .
H6 H 0.4235 0.5289 0.0905 0.057 Uiso 1 1 calc R . .
C7 C 0.2072(3) 0.2408(4) 0.1541(3) 0.0297(9) Uani 1 1 d . . .
C8 C 0.2997(3) 0.3343(4) 0.1716(3) 0.0299(9) Uani 1 1 d . . .
C9 C 0.0744(3) 0.1983(6) 0.0318(4) 0.0601(15) Uani 1 1 d . . .
H9A H 0.0695 0.1027 0.0588 0.072 Uiso 1 1 calc R . .
H9B H 0.0755 0.1836 -0.0311 0.072 Uiso 1 1 calc R . .
C10 C -0.0124(3) 0.2880(8) 0.0447(4) 0.083(2) Uani 1 1 d . . .
H10A H -0.0143 0.3016 0.1068 0.124 Uiso 1 1 calc R . .
H10B H -0.0697 0.2379 0.0187 0.124 Uiso 1 1 calc R . .
H10C H -0.0087 0.3818 0.0167 0.124 Uiso 1 1 calc R . .
C11 C 0.3864(3) 0.2275(5) 0.1995(3) 0.0345(10) Uani 1 1 d . . .
H11 H 0.3679 0.1593 0.2439 0.041 Uiso 1 1 calc R . .
C12 C 0.4733(3) 0.3066(6) 0.2387(3) 0.0532(13) Uani 1 1 d . . .
C13 C 0.4129(3) 0.1389(5) 0.1229(3) 0.0409(11) Uani 1 1 d . . .
C14 C 0.3543(4) -0.0265(7) 0.0097(4) 0.0647(16) Uani 1 1 d . . .
H14A H 0.3995 -0.1048 0.0284 0.078 Uiso 1 1 calc R . .
H14B H 0.3809 0.0333 -0.0336 0.078 Uiso 1 1 calc R . .
C15 C 0.2615(4) -0.0884(7) -0.0292(4) 0.0688(16) Uani 1 1 d . . .
H15A H 0.2363 -0.1488 0.0138 0.103 Uiso 1 1 calc R . .
H15B H 0.2704 -0.1467 -0.0799 0.103 Uiso 1 1 calc R . .
H15C H 0.2171 -0.0102 -0.0470 0.103 Uiso 1 1 calc R . .
C16 C 0.2898(3) 0.4403(5) 0.2487(3) 0.0336(10) Uani 1 1 d . . .
H16A H 0.2827 0.3829 0.3010 0.040 Uiso 1 1 calc R . .
H16B H 0.3490 0.4964 0.2614 0.040 Uiso 1 1 calc R . .
C17 C 0.2065(3) 0.5454(5) 0.2317(3) 0.0316(10) Uani 1 1 d . . .
C18 C 0.1138(3) 0.5058(5) 0.2448(3) 0.0410(11) Uani 1 1 d . . .
H18 H 0.1013 0.4117 0.2640 0.049 Uiso 1 1 calc R . .
C19 C 0.0409(3) 0.6065(6) 0.2291(3) 0.0489(12) Uani 1 1 d . . .
H19 H -0.0204 0.5769 0.2388 0.059 Uiso 1 1 calc R . .
C20 C 0.1402(4) 0.7801(6) 0.1891(3) 0.0589(14) Uani 1 1 d . . .
H20 H 0.1501 0.8750 0.1699 0.071 Uiso 1 1 calc R . .
C21 C 0.2182(3) 0.6882(5) 0.2032(3) 0.0454(12) Uani 1 1 d . . .
H21 H 0.2788 0.7213 0.1937 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 C7 1.215(5) . ?
O2 C13 1.200(5) . ?
O3 C13 1.314(5) . ?
O3 C14 1.455(5) . ?
N1 C7 1.354(5) . ?
N1 C4 1.416(5) . ?
N1 C9 1.465(5) . ?
N2 C12 1.135(6) . ?
N3 C19 1.319(7) . ?
N3 C20 1.340(6) . ?
C1 C2 1.370(8) . ?
C1 C6 1.391(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C5 C6 1.385(6) . ?
C5 C8 1.503(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.541(5) . ?
C8 C16 1.542(5) . ?
C8 C11 1.567(5) . ?
C9 C10 1.499(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.469(6) . ?
C11 C13 1.507(6) . ?
C11 H11 0.9800 . ?
C14 C15 1.464(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.505(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.387(5) . ?
C17 C21 1.389(6) . ?
C18 C19 1.369(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.369(6) . ?
C20 H20 0.9300 . ?
C21 H21 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
C13 O3 C14 116.2(3) . . ?
C7 N1 C4 111.5(3) . . ?
C7 N1 C9 122.8(4) . . ?
C4 N1 C9 125.6(4) . . ?
C19 N3 C20 115.2(4) . . ?
C2 C1 C6 120.9(5) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 121.1(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 117.7(5) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 122.5(4) . . ?
C3 C4 N1 128.4(4) . . ?
C5 C4 N1 109.0(3) . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 C8 131.5(4) . . ?
C4 C5 C8 109.3(3) . . ?
C5 C6 C1 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
O1 C7 N1 126.6(4) . . ?
O1 C7 C8 125.3(4) . . ?
N1 C7 C8 108.1(3) . . ?
C5 C8 C7 101.9(3) . . ?
C5 C8 C16 115.5(3) . . ?
C7 C8 C16 108.5(3) . . ?
C5 C8 C11 113.4(3) . . ?
C7 C8 C11 107.7(3) . . ?
C16 C8 C11 109.2(3) . . ?
N1 C9 C10 112.3(4) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
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 . . ?
C12 C11 C13 107.4(3) . . ?
C12 C11 C8 111.9(4) . . ?
C13 C11 C8 112.7(3) . . ?
C12 C11 H11 108.2 . . ?
C13 C11 H11 108.2 . . ?
C8 C11 H11 108.2 . . ?
N2 C12 C11 179.3(6) . . ?
O2 C13 O3 125.8(4) . . ?
O2 C13 C11 123.5(4) . . ?
O3 C13 C11 110.7(3) . . ?
O3 C14 C15 108.3(4) . . ?
O3 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C8 114.6(3) . . ?
C17 C16 H16A 108.6 . . ?
C8 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C8 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C21 116.3(4) . . ?
C18 C17 C16 121.8(4) . . ?
C21 C17 C16 121.9(4) . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
N3 C19 C18 125.3(4) . . ?
N3 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
N3 C20 C21 124.3(5) . . ?
N3 C20 H20 117.9 . . ?
C21 C20 H20 117.9 . . ?
C20 C21 C17 119.7(4) . . ?
C20 C21 H21 120.2 . . ?
C17 C21 H21 120.2 . . ?

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 0.0(9) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C2 C3 C4 N1 -178.0(5) . . . . ?
C7 N1 C4 C3 174.6(4) . . . . ?
C9 N1 C4 C3 -1.2(7) . . . . ?
C7 N1 C4 C5 -3.3(5) . . . . ?
C9 N1 C4 C5 -179.0(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
N1 C4 C5 C6 179.2(4) . . . . ?
C3 C4 C5 C8 -177.5(4) . . . . ?
N1 C4 C5 C8 0.5(4) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C8 C5 C6 C1 176.9(4) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C4 N1 C7 O1 -175.7(4) . . . . ?
C9 N1 C7 O1 0.2(6) . . . . ?
C4 N1 C7 C8 4.5(4) . . . . ?
C9 N1 C7 C8 -179.6(4) . . . . ?
C6 C5 C8 C7 -176.5(4) . . . . ?
C4 C5 C8 C7 2.0(4) . . . . ?
C6 C5 C8 C16 66.1(5) . . . . ?
C4 C5 C8 C16 -115.4(4) . . . . ?
C6 C5 C8 C11 -61.0(6) . . . . ?
C4 C5 C8 C11 117.4(4) . . . . ?
O1 C7 C8 C5 176.3(4) . . . . ?
N1 C7 C8 C5 -3.9(4) . . . . ?
O1 C7 C8 C16 -61.4(5) . . . . ?
N1 C7 C8 C16 118.5(3) . . . . ?
O1 C7 C8 C11 56.7(5) . . . . ?
N1 C7 C8 C11 -123.4(3) . . . . ?
C7 N1 C9 C10 92.2(6) . . . . ?
C4 N1 C9 C10 -92.5(6) . . . . ?
C5 C8 C11 C12 82.2(4) . . . . ?
C7 C8 C11 C12 -165.8(4) . . . . ?
C16 C8 C11 C12 -48.2(5) . . . . ?
C5 C8 C11 C13 -39.0(5) . . . . ?
C7 C8 C11 C13 73.0(4) . . . . ?
C16 C8 C11 C13 -169.4(3) . . . . ?
C13 C11 C12 N2 33(51) . . . . ?
C8 C11 C12 N2 -91(51) . . . . ?
C14 O3 C13 O2 0.3(7) . . . . ?
C14 O3 C13 C11 179.2(4) . . . . ?
C12 C11 C13 O2 -2.2(6) . . . . ?
C8 C11 C13 O2 121.5(5) . . . . ?
C12 C11 C13 O3 178.8(4) . . . . ?
C8 C11 C13 O3 -57.5(5) . . . . ?
C13 O3 C14 C15 -173.2(4) . . . . ?
C5 C8 C16 C17 53.0(5) . . . . ?
C7 C8 C16 C17 -60.7(4) . . . . ?
C11 C8 C16 C17 -177.8(3) . . . . ?
C8 C16 C17 C18 83.4(5) . . . . ?
C8 C16 C17 C21 -97.6(5) . . . . ?
C21 C17 C18 C19 0.2(6) . . . . ?
C16 C17 C18 C19 179.3(4) . . . . ?
C20 N3 C19 C18 -0.7(8) . . . . ?
C17 C18 C19 N3 0.4(7) . . . . ?
C19 N3 C20 C21 0.3(8) . . . . ?
N3 C20 C21 C17 0.2(8) . . . . ?
C18 C17 C21 C20 -0.5(6) . . . . ?
C16 C17 C21 C20 -179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.080
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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_expt_363
_database_code_depnum_ccdc_archive 'CCDC 1053587'
_audit_update_record             
;
2015-03-12 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N5 O'
_chemical_formula_sum            'C22 H19 N5 O'
_chemical_formula_weight         369.42

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           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                   12.3799(12)
_cell_length_b                   13.0555(12)
_cell_length_c                   11.5532(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.570(5)
_cell_angle_gamma                90.00
_cell_volume                     1846.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7218
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      28.07

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   'Bruker 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            19861
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4016
_reflns_number_gt                3086
_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)+(0.0810P)²+0.5940P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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 0.24953(13) 0.16401(11) 0.16615(13) 0.0522(4) Uani 1 1 d . . .
N1 N 0.17466(13) 0.04648(13) 0.02887(14) 0.0417(4) Uani 1 1 d . . .
N2 N 0.36422(12) 0.07008(12) 0.41510(13) 0.0372(4) Uani 1 1 d . . .
N3 N 0.51307(13) 0.05936(13) 0.32564(14) 0.0436(4) Uani 1 1 d . . .
N4 N 0.22649(14) 0.07254(16) 0.53139(15) 0.0553(5) Uani 1 1 d . . .
H4NA H 0.1609 0.0609 0.5440 0.066 Uiso 1 1 calc R . .
H4NB H 0.2731 0.0999 0.5851 0.066 Uiso 1 1 calc R . .
N5 N -0.00842(14) -0.03175(16) 0.36296(16) 0.0541(5) Uani 1 1 d . . .
C1 C 0.08478(19) -0.25454(18) 0.0737(2) 0.0609(7) Uani 1 1 d . . .
H1 H 0.0663 -0.3221 0.0872 0.073 Uiso 1 1 calc R . .
C2 C 0.05741(19) -0.2132(2) -0.0360(2) 0.0618(7) Uani 1 1 d . . .
H2 H 0.0199 -0.2533 -0.0953 0.074 Uiso 1 1 calc R . .
C3 C 0.08431(18) -0.11341(19) -0.0604(2) 0.0543(6) Uani 1 1 d . . .
H3 H 0.0660 -0.0860 -0.1350 0.065 Uiso 1 1 calc R . .
C4 C 0.13945(15) -0.05601(15) 0.03051(17) 0.0419(5) Uani 1 1 d . . .
C5 C 0.16673(15) -0.09627(15) 0.14254(17) 0.0399(4) Uani 1 1 d . . .
C6 C 0.14015(17) -0.19617(16) 0.1653(2) 0.0504(5) Uani 1 1 d . . .
H6 H 0.1586 -0.2240 0.2397 0.060 Uiso 1 1 calc R . .
C7 C 0.21968(15) 0.07778(15) 0.13831(16) 0.0383(4) Uani 1 1 d . . .
C8 C 0.22914(15) -0.01657(14) 0.21984(15) 0.0359(4) Uani 1 1 d . . .
C9 C 0.18966(14) 0.00438(14) 0.33572(15) 0.0355(4) Uani 1 1 d . . .
C10 C 0.25620(15) 0.04799(15) 0.42749(16) 0.0378(4) Uani 1 1 d . . .
C11 C 0.41387(15) 0.02761(15) 0.32595(16) 0.0386(4) Uani 1 1 d . . .
C12 C 0.35143(15) -0.04662(15) 0.24502(17) 0.0422(5) Uani 1 1 d . . .
H12A H 0.3584 -0.1145 0.2794 0.051 Uiso 1 1 calc R . .
H12B H 0.3814 -0.0485 0.1721 0.051 Uiso 1 1 calc R . .
C13 C 0.44078(15) 0.13846(14) 0.47546(16) 0.0382(4) Uani 1 1 d . . .
C14 C 0.53200(16) 0.12966(15) 0.41754(17) 0.0416(4) Uani 1 1 d . . .
C15 C 0.43857(17) 0.20714(16) 0.56598(18) 0.0475(5) Uani 1 1 d . . .
H15 H 0.3781 0.2129 0.6046 0.057 Uiso 1 1 calc R . .
C16 C 0.5308(2) 0.26714(18) 0.5966(2) 0.0568(6) Uani 1 1 d . . .
H16 H 0.5318 0.3146 0.6568 0.068 Uiso 1 1 calc R . .
C17 C 0.6218(2) 0.25831(19) 0.5400(2) 0.0584(6) Uani 1 1 d . . .
H17 H 0.6822 0.2997 0.5631 0.070 Uiso 1 1 calc R . .
C18 C 0.62390(17) 0.18959(19) 0.4506(2) 0.0535(5) Uani 1 1 d . . .
H18 H 0.6852 0.1833 0.4133 0.064 Uiso 1 1 calc R . .
C19 C 0.08006(15) -0.01663(14) 0.34925(16) 0.0380(4) Uani 1 1 d . . .
C20 C 0.16299(19) 0.11210(19) -0.07436(18) 0.0547(6) Uani 1 1 d . . .
H20A H 0.1773 0.1825 -0.0498 0.066 Uiso 1 1 calc R . .
H20B H 0.0882 0.1083 -0.1138 0.066 Uiso 1 1 calc R . .
C21 C 0.2406(2) 0.0822(3) -0.1610(2) 0.0795(9) Uani 1 1 d . . .
H21A H 0.2172 0.0164 -0.1948 0.095 Uiso 1 1 calc R . .
H21B H 0.2320 0.1319 -0.2240 0.095 Uiso 1 1 calc R . .
C22 C 0.3557(3) 0.0750(4) -0.1153(3) 0.1109(14) Uani 1 1 d . . .
H22A H 0.3826 0.1413 -0.0891 0.166 Uiso 1 1 calc R . .
H22B H 0.3950 0.0511 -0.1757 0.166 Uiso 1 1 calc R . .
H22C H 0.3660 0.0279 -0.0507 0.166 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 C7 1.213(2) . ?
N1 C7 1.366(2) . ?
N1 C4 1.408(3) . ?
N1 C20 1.458(3) . ?
N2 C11 1.391(2) . ?
N2 C10 1.396(2) . ?
N2 C13 1.409(2) . ?
N3 C11 1.297(2) . ?
N3 C14 1.397(3) . ?
N4 C10 1.346(2) . ?
N4 H4NA 0.8600 . ?
N4 H4NB 0.8600 . ?
N5 C19 1.147(2) . ?
C1 C2 1.372(4) . ?
C1 C6 1.398(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C5 C6 1.380(3) . ?
C5 C8 1.507(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.544(3) . ?
C8 C9 1.517(2) . ?
C8 C12 1.549(3) . ?
C9 C10 1.366(3) . ?
C9 C19 1.416(2) . ?
C11 C12 1.482(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.381(3) . ?
C13 C14 1.401(3) . ?
C14 C18 1.387(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C21 1.538(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.447(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C7 N1 C4 110.86(16) . . ?
C7 N1 C20 123.94(18) . . ?
C4 N1 C20 125.18(17) . . ?
C11 N2 C10 121.96(16) . . ?
C11 N2 C13 106.27(14) . . ?
C10 N2 C13 131.63(15) . . ?
C11 N3 C14 105.05(15) . . ?
C10 N4 H4NA 120.0 . . ?
C10 N4 H4NB 120.0 . . ?
H4NA N4 H4NB 120.0 . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 117.5(2) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 N1 128.5(2) . . ?
C5 C4 N1 109.81(17) . . ?
C6 C5 C4 120.17(19) . . ?
C6 C5 C8 130.95(19) . . ?
C4 C5 C8 108.80(16) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O1 C7 N1 126.09(18) . . ?
O1 C7 C8 125.88(17) . . ?
N1 C7 C8 108.02(16) . . ?
C5 C8 C9 116.31(15) . . ?
C5 C8 C7 101.75(15) . . ?
C9 C8 C7 112.91(14) . . ?
C5 C8 C12 109.69(14) . . ?
C9 C8 C12 108.32(15) . . ?
C7 C8 C12 107.44(14) . . ?
C10 C9 C19 118.17(15) . . ?
C10 C9 C8 121.58(15) . . ?
C19 C9 C8 120.18(16) . . ?
N4 C10 C9 125.33(17) . . ?
N4 C10 N2 115.82(17) . . ?
C9 C10 N2 118.85(15) . . ?
N3 C11 N2 113.45(17) . . ?
N3 C11 C12 127.78(16) . . ?
N2 C11 C12 118.77(16) . . ?
C11 C12 C8 110.87(15) . . ?
C11 C12 H12A 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C15 C13 C14 121.56(18) . . ?
C15 C13 N2 134.31(17) . . ?
C14 C13 N2 104.03(16) . . ?
C18 C14 N3 128.17(18) . . ?
C18 C14 C13 120.59(19) . . ?
N3 C14 C13 111.18(17) . . ?
C13 C15 C16 116.86(19) . . ?
C13 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C14 118.0(2) . . ?
C17 C18 H18 121.0 . . ?
C14 C18 H18 121.0 . . ?
N5 C19 C9 178.0(2) . . ?
N1 C20 C21 112.8(2) . . ?
N1 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N1 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 117.1(2) . . ?
C22 C21 H21A 108.0 . . ?
C20 C21 H21A 108.0 . . ?
C22 C21 H21B 108.0 . . ?
C20 C21 H21B 108.0 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 0.7(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 N1 -179.25(19) . . . . ?
C7 N1 C4 C3 175.83(18) . . . . ?
C20 N1 C4 C3 -2.8(3) . . . . ?
C7 N1 C4 C5 -3.2(2) . . . . ?
C20 N1 C4 C5 178.08(17) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
N1 C4 C5 C6 179.97(17) . . . . ?
C3 C4 C5 C8 178.08(17) . . . . ?
N1 C4 C5 C8 -2.8(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C8 C5 C6 C1 -177.16(18) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C4 N1 C7 O1 -173.98(18) . . . . ?
C20 N1 C7 O1 4.7(3) . . . . ?
C4 N1 C7 C8 7.7(2) . . . . ?
C20 N1 C7 C8 -173.63(16) . . . . ?
C6 C5 C8 C9 -53.2(3) . . . . ?
C4 C5 C8 C9 129.93(17) . . . . ?
C6 C5 C8 C7 -176.33(19) . . . . ?
C4 C5 C8 C7 6.81(18) . . . . ?
C6 C5 C8 C12 70.1(2) . . . . ?
C4 C5 C8 C12 -106.74(17) . . . . ?
O1 C7 C8 C5 172.95(18) . . . . ?
N1 C7 C8 C5 -8.70(18) . . . . ?
O1 C7 C8 C9 47.5(2) . . . . ?
N1 C7 C8 C9 -134.12(16) . . . . ?
O1 C7 C8 C12 -71.8(2) . . . . ?
N1 C7 C8 C12 106.51(16) . . . . ?
C5 C8 C9 C10 158.81(18) . . . . ?
C7 C8 C9 C10 -84.1(2) . . . . ?
C12 C8 C9 C10 34.8(2) . . . . ?
C5 C8 C9 C19 -24.3(2) . . . . ?
C7 C8 C9 C19 92.8(2) . . . . ?
C12 C8 C9 C19 -148.31(17) . . . . ?
C19 C9 C10 N4 0.4(3) . . . . ?
C8 C9 C10 N4 177.40(19) . . . . ?
C19 C9 C10 N2 -179.39(17) . . . . ?
C8 C9 C10 N2 -2.4(3) . . . . ?
C11 N2 C10 N4 164.15(18) . . . . ?
C13 N2 C10 N4 -20.9(3) . . . . ?
C11 N2 C10 C9 -16.0(3) . . . . ?
C13 N2 C10 C9 158.97(19) . . . . ?
C14 N3 C11 N2 -1.6(2) . . . . ?
C14 N3 C11 C12 178.85(19) . . . . ?
C10 N2 C11 N3 177.81(17) . . . . ?
C13 N2 C11 N3 1.7(2) . . . . ?
C10 N2 C11 C12 -2.6(3) . . . . ?
C13 N2 C11 C12 -178.72(16) . . . . ?
N3 C11 C12 C8 -144.31(19) . . . . ?
N2 C11 C12 C8 36.2(2) . . . . ?
C5 C8 C12 C11 -177.03(15) . . . . ?
C9 C8 C12 C11 -49.1(2) . . . . ?
C7 C8 C12 C11 73.14(19) . . . . ?
C11 N2 C13 C15 175.4(2) . . . . ?
C10 N2 C13 C15 -0.2(4) . . . . ?
C11 N2 C13 C14 -0.98(19) . . . . ?
C10 N2 C13 C14 -176.54(19) . . . . ?
C11 N3 C14 C18 -176.4(2) . . . . ?
C11 N3 C14 C13 1.0(2) . . . . ?
C15 C13 C14 C18 0.6(3) . . . . ?
N2 C13 C14 C18 177.60(18) . . . . ?
C15 C13 C14 N3 -176.91(18) . . . . ?
N2 C13 C14 N3 0.0(2) . . . . ?
C14 C13 C15 C16 0.2(3) . . . . ?
N2 C13 C15 C16 -175.7(2) . . . . ?
C13 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C14 0.6(4) . . . . ?
N3 C14 C18 C17 176.1(2) . . . . ?
C13 C14 C18 C17 -1.0(3) . . . . ?
C10 C9 C19 N5 17(7) . . . . ?
C8 C9 C19 N5 -160(6) . . . . ?
C7 N1 C20 C21 109.4(2) . . . . ?
C4 N1 C20 C21 -72.1(3) . . . . ?
N1 C20 C21 C22 -53.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.046

#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
