# 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_compound_3c
_database_code_depnum_ccdc_archive 'CCDC 1028616'
_audit_update_record             
;
2014-10-11 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (E)-1-nitro-4-styrylbenzene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N O2'
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24

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 -1'
_Hall_group                      '-P 1'
_ADDSYM_Pseudo/New_Space_group   Pbca

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

_cell_length_a                   7.890(3)
_cell_length_b                   10.185(4)
_cell_length_c                   28.422(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2284.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      24.990

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.44
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22049
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.1303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         24.99
_reflns_number_total             8046
_reflns_number_gt                2999
_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    '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)+(0.1027P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8026
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2395
_refine_ls_R_factor_gt           0.0952
_refine_ls_wR_factor_ref         0.2695
_refine_ls_wR_factor_gt          0.2011
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.011

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 0.3251(7) 0.4765(6) 0.3996(2) 0.0674(17) Uani 1 1 d . . .
H1 H 0.2913 0.5448 0.3800 0.081 Uiso 1 1 calc R . .
C2 C 0.4071(7) 0.3686(7) 0.3806(2) 0.0622(16) Uani 1 1 d . . .
C3 C 0.4084(7) 0.3943(6) 0.2439(2) 0.0565(15) Uani 1 1 d . . .
C4 C 0.3451(7) 0.3825(6) 0.4759(2) 0.0580(15) Uani 1 1 d . . .
N3 N 0.3082(8) 0.3869(6) 0.5266(2) 0.0790(16) Uani 1 1 d . . .
C5 C 0.3380(7) 0.4843(5) 0.2131(2) 0.0610(15) Uani 1 1 d . . .
H5 H 0.2781 0.5556 0.2249 0.073 Uiso 1 1 calc R . .
C6 C 0.4998(7) 0.2916(6) 0.2251(2) 0.0632(16) Uani 1 1 d . . .
H6 H 0.5503 0.2307 0.2450 0.076 Uiso 1 1 calc R . .
C7 C 0.3550(7) 0.4700(6) 0.1655(2) 0.0671(17) Uani 1 1 d . . .
H7 H 0.3058 0.5310 0.1454 0.081 Uiso 1 1 calc R . .
C8 C 0.3798(7) 0.4176(6) 0.2957(3) 0.076(2) Uani 1 1 d . . .
H8 H 0.3132 0.4891 0.3043 0.091 Uiso 1 1 calc R . .
O4 O 0.3617(7) 0.3013(5) 0.55117(17) 0.1133(18) Uani 1 1 d . . .
C9 C 0.5172(7) 0.2783(6) 0.1777(3) 0.0737(18) Uani 1 1 d . . .
H9 H 0.5794 0.2085 0.1657 0.088 Uiso 1 1 calc R . .
C10 C 0.4292(8) 0.2784(6) 0.4576(2) 0.0701(17) Uani 1 1 d . . .
H10 H 0.4661 0.2115 0.4774 0.084 Uiso 1 1 calc R . .
C11 C 0.4595(7) 0.2710(6) 0.4114(3) 0.0737(18) Uani 1 1 d . . .
H11 H 0.5173 0.1986 0.3996 0.088 Uiso 1 1 calc R . .
C12 C 0.4391(8) 0.3476(6) 0.3282(3) 0.085(2) Uani 1 1 d . . .
H12 H 0.5080 0.2776 0.3196 0.102 Uiso 1 1 calc R . .
C13 C 0.2929(7) 0.4837(6) 0.4472(2) 0.0666(17) Uani 1 1 d . . .
H13 H 0.2367 0.5559 0.4597 0.080 Uiso 1 1 calc R . .
C14 C 0.4438(7) 0.3668(7) 0.1475(2) 0.0682(17) Uani 1 1 d . . .
H14 H 0.4545 0.3565 0.1151 0.082 Uiso 1 1 calc R . .
O3 O 0.2216(8) 0.4786(6) 0.54045(18) 0.127(2) Uani 1 1 d . . .
C15 C 0.8811(7) 0.5850(6) 0.2038(3) 0.0736(19) Uani 1 1 d . . .
H15 H 0.8131 0.5142 0.1955 0.088 Uiso 1 1 calc R . .
C16 C 0.9080(7) 0.6315(7) 0.1193(2) 0.0608(16) Uani 1 1 d . . .
C17 C 0.4100(7) 0.8943(6) 0.2559(2) 0.0561(15) Uani 1 1 d . . .
C18 C 0.8453(7) 0.6157(6) 0.0244(2) 0.0576(15) Uani 1 1 d . . .
C19 C 0.8245(7) 0.5241(6) 0.1005(2) 0.0699(17) Uani 1 1 d . . .
H19 H 0.7889 0.4569 0.1204 0.084 Uiso 1 1 calc R . .
C20 C 0.3252(7) 0.9762(6) 0.1004(2) 0.0681(17) Uani 1 1 d . . .
H20 H 0.2917 1.0445 0.1200 0.082 Uiso 1 1 calc R . .
C21 C 0.9093(7) 0.6060(6) 0.2561(2) 0.0544(15) Uani 1 1 d . . .
C22 C 0.4071(7) 0.8681(7) 0.1192(2) 0.0631(16) Uani 1 1 d . . .
C23 C 0.8377(7) 0.5153(6) 0.2862(2) 0.0640(16) Uani 1 1 d . . .
H23 H 0.7777 0.4446 0.2739 0.077 Uiso 1 1 calc R . .
C24 C 0.3463(7) 0.8830(6) 0.0243(2) 0.0572(15) Uani 1 1 d . . .
C25 C 0.3369(7) 0.9840(6) 0.2863(2) 0.0653(16) Uani 1 1 d . . .
H25 H 0.2751 1.0541 0.2743 0.078 Uiso 1 1 calc R . .
C26 C 1.0004(7) 0.7088(6) 0.2753(2) 0.0648(16) Uani 1 1 d . . .
H26 H 1.0521 0.7701 0.2558 0.078 Uiso 1 1 calc R . .
N2 N 0.3068(8) 0.8875(6) -0.0261(2) 0.0802(16) Uani 1 1 d . . .
C27 C 1.0145(7) 0.7203(6) 0.3231(3) 0.0691(17) Uani 1 1 d . . .
H27 H 1.0740 0.7909 0.3357 0.083 Uiso 1 1 calc R . .
O2 O 0.3615(7) 0.8010(6) -0.05137(18) 0.1148(19) Uani 1 1 d . . .
C28 C 0.3803(7) 0.9163(6) 0.2040(3) 0.0758(19) Uani 1 1 d . . .
H28 H 0.3123 0.9872 0.1956 0.091 Uiso 1 1 calc R . .
C29 C 0.8539(7) 0.5282(6) 0.3340(2) 0.0663(16) Uani 1 1 d . . .
H29 H 0.8037 0.4668 0.3538 0.080 Uiso 1 1 calc R . .
C30 C 0.5163(7) 0.7789(6) 0.3224(3) 0.0715(18) Uani 1 1 d . . .
H30 H 0.5787 0.7089 0.3343 0.086 Uiso 1 1 calc R . .
N1 N 0.8061(8) 0.6107(6) -0.0265(2) 0.0800(16) Uani 1 1 d . . .
C31 C 0.4292(7) 0.7783(6) 0.0423(2) 0.0695(17) Uani 1 1 d . . .
H31 H 0.4659 0.7115 0.0225 0.083 Uiso 1 1 calc R . .
C32 C 0.4988(7) 0.7920(6) 0.2753(2) 0.0664(16) Uani 1 1 d . . .
H32 H 0.5483 0.7301 0.2555 0.080 Uiso 1 1 calc R . .
C33 C 0.4388(8) 0.8478(6) 0.1713(3) 0.082(2) Uani 1 1 d . . .
H33 H 0.5082 0.7778 0.1797 0.099 Uiso 1 1 calc R . .
C34 C 0.4588(7) 0.7704(6) 0.0886(3) 0.0747(18) Uani 1 1 d . . .
H34 H 0.5156 0.6975 0.1004 0.090 Uiso 1 1 calc R . .
C35 C 0.7930(7) 0.5148(6) 0.0529(2) 0.0655(16) Uani 1 1 d . . .
H35 H 0.7378 0.4421 0.0405 0.079 Uiso 1 1 calc R . .
C36 C 0.2929(7) 0.9837(6) 0.0526(2) 0.0662(16) Uani 1 1 d . . .
H36 H 0.2361 1.0556 0.0400 0.079 Uiso 1 1 calc R . .
C37 C 0.9386(8) 0.6516(7) 0.1709(3) 0.082(2) Uani 1 1 d . . .
H37 H 1.0083 0.7216 0.1791 0.098 Uiso 1 1 calc R . .
C38 C 0.9590(7) 0.7283(6) 0.0882(3) 0.0723(18) Uani 1 1 d . . .
H38 H 1.0160 0.8011 0.1000 0.087 Uiso 1 1 calc R . .
C39 C 0.4436(7) 0.8670(7) 0.3530(2) 0.0707(17) Uani 1 1 d . . .
H39 H 0.4541 0.8570 0.3854 0.085 Uiso 1 1 calc R . .
C40 C 0.3552(7) 0.9700(6) 0.3341(2) 0.0696(17) Uani 1 1 d . . .
H40 H 0.3065 1.0318 0.3540 0.084 Uiso 1 1 calc R . .
O8 O 0.8608(7) 0.6989(5) -0.05107(18) 0.1124(18) Uani 1 1 d . . .
C41 C 0.9434(7) 0.6307(7) 0.3529(2) 0.0696(17) Uani 1 1 d . . .
H41 H 0.9555 0.6391 0.3853 0.083 Uiso 1 1 calc R . .
C42 C 0.9296(8) 0.7215(6) 0.0420(2) 0.0683(17) Uani 1 1 d . . .
H42 H 0.9663 0.7881 0.0220 0.082 Uiso 1 1 calc R . .
O1 O 0.2227(8) 0.9780(6) -0.04082(19) 0.128(2) Uani 1 1 d . . .
O7 O 0.7218(8) 0.5202(6) -0.04062(19) 0.130(2) Uani 1 1 d . . .
C43 C 0.9084(7) 0.1320(7) 0.3806(2) 0.0615(16) Uani 1 1 d . . .
C44 C 0.9096(7) 0.1059(6) 0.2441(2) 0.0555(15) Uani 1 1 d . . .
C45 C 0.9980(7) 0.2083(6) 0.2245(2) 0.0647(16) Uani 1 1 d . . .
H45 H 1.0476 0.2703 0.2442 0.078 Uiso 1 1 calc R . .
C46 C 0.8466(7) 0.1166(6) 0.4757(2) 0.0566(15) Uani 1 1 d . . .
N4 N 0.8080(8) 0.1137(6) 0.5265(2) 0.0791(16) Uani 1 1 d . . .
C47 C 0.8806(7) 0.0838(6) 0.2964(3) 0.0750(19) Uani 1 1 d . . .
H47 H 0.8131 0.0127 0.3048 0.090 Uiso 1 1 calc R . .
C48 C 0.8371(7) 0.0155(6) 0.2138(2) 0.0646(16) Uani 1 1 d . . .
H48 H 0.7760 -0.0549 0.2259 0.078 Uiso 1 1 calc R . .
C49 C 0.8265(7) 0.0234(6) 0.3990(2) 0.0668(17) Uani 1 1 d . . .
H49 H 0.7934 -0.0446 0.3792 0.080 Uiso 1 1 calc R . .
C50 C 0.8546(7) 0.0288(6) 0.1659(2) 0.0659(16) Uani 1 1 d . . .
H50 H 0.8057 -0.0328 0.1459 0.079 Uiso 1 1 calc R . .
C51 C 0.9281(7) 0.2222(6) 0.4580(2) 0.0693(17) Uani 1 1 d . . .
H51 H 0.9615 0.2903 0.4777 0.083 Uiso 1 1 calc R . .
O6 O 0.8618(7) 0.1991(5) 0.55162(17) 0.1120(19) Uani 1 1 d . . .
C52 C 1.0152(7) 0.2218(6) 0.1771(3) 0.0714(18) Uani 1 1 d . . .
H52 H 1.0759 0.2922 0.1649 0.086 Uiso 1 1 calc R . .
C53 C 0.9606(7) 0.2280(6) 0.4118(3) 0.0735(18) Uani 1 1 d . . .
H53 H 1.0207 0.2996 0.4002 0.088 Uiso 1 1 calc R . .
C54 C 0.9386(8) 0.1521(6) 0.3292(3) 0.083(2) Uani 1 1 d . . .
H54 H 1.0075 0.2224 0.3208 0.100 Uiso 1 1 calc R . .
C55 C 0.7937(7) 0.0157(6) 0.4469(2) 0.0670(17) Uani 1 1 d . . .
H55 H 0.7368 -0.0563 0.4593 0.080 Uiso 1 1 calc R . .
C56 C 0.9433(8) 0.1318(7) 0.1473(2) 0.0694(17) Uani 1 1 d . . .
H56 H 0.9546 0.1407 0.1149 0.083 Uiso 1 1 calc R . .
O5 O 0.7251(8) 0.0216(6) 0.54092(18) 0.127(2) 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 C13 1.377(7) . ?
C1 C2 1.385(8) . ?
C1 H1 0.9300 . ?
C2 C11 1.387(8) . ?
C2 C12 1.525(9) . ?
C3 C6 1.378(7) . ?
C3 C5 1.384(7) . ?
C3 C8 1.510(8) . ?
C4 C10 1.353(8) . ?
C4 C13 1.378(7) . ?
C4 N3 1.471(8) . ?
N3 O4 1.195(6) . ?
N3 O3 1.222(7) . ?
C5 C7 1.365(7) . ?
C5 H5 0.9300 . ?
C6 C9 1.359(8) . ?
C6 H6 0.9300 . ?
C7 C14 1.363(8) . ?
C7 H7 0.9300 . ?
C8 C12 1.256(8) . ?
C8 H8 0.9300 . ?
C9 C14 1.373(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.338(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C37 1.242(8) . ?
C15 C21 1.518(8) . ?
C15 H15 0.9300 . ?
C16 C19 1.384(8) . ?
C16 C38 1.383(8) . ?
C16 C37 1.500(9) . ?
C17 C32 1.371(7) . ?
C17 C25 1.382(7) . ?
C17 C28 1.511(8) . ?
C18 C42 1.361(8) . ?
C18 C35 1.372(7) . ?
C18 N1 1.482(8) . ?
C19 C35 1.379(8) . ?
C19 H19 0.9300 . ?
C20 C36 1.384(8) . ?
C20 C22 1.385(8) . ?
C20 H20 0.9300 . ?
C21 C23 1.379(7) . ?
C21 C26 1.382(7) . ?
C22 C34 1.383(8) . ?
C22 C33 1.514(9) . ?
C23 C29 1.370(8) . ?
C23 H23 0.9300 . ?
C24 C31 1.352(8) . ?
C24 C36 1.370(7) . ?
C24 N2 1.466(8) . ?
C25 C40 1.373(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(8) . ?
C26 H26 0.9300 . ?
N2 O1 1.210(7) . ?
N2 O2 1.216(6) . ?
C27 C41 1.365(8) . ?
C27 H27 0.9300 . ?
C28 C33 1.252(8) . ?
C28 H28 0.9300 . ?
C29 C41 1.370(8) . ?
C29 H29 0.9300 . ?
C30 C32 1.353(8) . ?
C30 C39 1.375(8) . ?
C30 H30 0.9300 . ?
N1 O7 1.205(7) . ?
N1 O8 1.217(6) . ?
C31 C34 1.338(8) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 C42 1.337(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.370(8) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C53 1.382(8) . ?
C43 C49 1.384(8) . ?
C43 C54 1.493(9) . ?
C44 C45 1.373(7) . ?
C44 C48 1.386(7) . ?
C44 C47 1.520(8) . ?
C45 C52 1.361(8) . ?
C45 H45 0.9300 . ?
C46 C51 1.350(8) . ?
C46 C55 1.379(7) . ?
C46 N4 1.475(8) . ?
N4 O6 1.202(6) . ?
N4 O5 1.215(7) . ?
C47 C54 1.251(8) . ?
C47 H47 0.9300 . ?
C48 C50 1.374(7) . ?
C48 H48 0.9300 . ?
C49 C55 1.386(8) . ?
C49 H49 0.9300 . ?
C50 C56 1.366(8) . ?
C50 H50 0.9300 . ?
C51 C53 1.339(8) . ?
C51 H51 0.9300 . ?
C52 C56 1.370(8) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C56 H56 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 C1 C2 120.8(6) . . ?
C13 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C11 117.4(6) . . ?
C1 C2 C12 124.7(6) . . ?
C11 C2 C12 117.8(6) . . ?
C6 C3 C5 117.8(5) . . ?
C6 C3 C8 125.2(6) . . ?
C5 C3 C8 117.0(6) . . ?
C10 C4 C13 120.4(6) . . ?
C10 C4 N3 119.8(6) . . ?
C13 C4 N3 119.9(6) . . ?
O4 N3 O3 124.5(7) . . ?
O4 N3 C4 118.7(6) . . ?
O3 N3 C4 116.8(6) . . ?
C7 C5 C3 121.1(6) . . ?
C7 C5 H5 119.5 . . ?
C3 C5 H5 119.5 . . ?
C9 C6 C3 120.8(6) . . ?
C9 C6 H6 119.6 . . ?
C3 C6 H6 119.6 . . ?
C14 C7 C5 120.3(6) . . ?
C14 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C12 C8 C3 124.9(7) . . ?
C12 C8 H8 117.6 . . ?
C3 C8 H8 117.6 . . ?
C6 C9 C14 120.7(6) . . ?
C6 C9 H9 119.6 . . ?
C14 C9 H9 119.6 . . ?
C11 C10 C4 120.5(6) . . ?
C11 C10 H10 119.7 . . ?
C4 C10 H10 119.7 . . ?
C10 C11 C2 121.8(6) . . ?
C10 C11 H11 119.1 . . ?
C2 C11 H11 119.1 . . ?
C8 C12 C2 125.2(7) . . ?
C8 C12 H12 117.4 . . ?
C2 C12 H12 117.4 . . ?
C1 C13 C4 119.1(6) . . ?
C1 C13 H13 120.5 . . ?
C4 C13 H13 120.5 . . ?
C7 C14 C9 119.2(6) . . ?
C7 C14 H14 120.4 . . ?
C9 C14 H14 120.4 . . ?
C37 C15 C21 127.5(7) . . ?
C37 C15 H15 116.3 . . ?
C21 C15 H15 116.3 . . ?
C19 C16 C38 117.1(6) . . ?
C19 C16 C37 124.1(6) . . ?
C38 C16 C37 118.7(6) . . ?
C32 C17 C25 117.8(6) . . ?
C32 C17 C28 125.7(6) . . ?
C25 C17 C28 116.5(6) . . ?
C42 C18 C35 121.6(6) . . ?
C42 C18 N1 119.2(6) . . ?
C35 C18 N1 119.2(6) . . ?
C35 C19 C16 121.2(6) . . ?
C35 C19 H19 119.4 . . ?
C16 C19 H19 119.4 . . ?
C36 C20 C22 120.6(6) . . ?
C36 C20 H20 119.7 . . ?
C22 C20 H20 119.7 . . ?
C23 C21 C26 118.4(6) . . ?
C23 C21 C15 116.9(6) . . ?
C26 C21 C15 124.7(6) . . ?
C34 C22 C20 117.8(6) . . ?
C34 C22 C33 117.9(6) . . ?
C20 C22 C33 124.3(6) . . ?
C29 C23 C21 120.8(6) . . ?
C29 C23 H23 119.6 . . ?
C21 C23 H23 119.6 . . ?
C31 C24 C36 121.1(6) . . ?
C31 C24 N2 119.9(6) . . ?
C36 C24 N2 119.0(6) . . ?
C40 C25 C17 120.3(6) . . ?
C40 C25 H25 119.8 . . ?
C17 C25 H25 119.8 . . ?
C27 C26 C21 119.9(6) . . ?
C27 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
O1 N2 O2 122.8(7) . . ?
O1 N2 C24 118.5(6) . . ?
O2 N2 C24 118.6(7) . . ?
C41 C27 C26 121.7(6) . . ?
C41 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C33 C28 C17 125.9(7) . . ?
C33 C28 H28 117.1 . . ?
C17 C28 H28 117.1 . . ?
C41 C29 C23 120.7(6) . . ?
C41 C29 H29 119.7 . . ?
C23 C29 H29 119.7 . . ?
C32 C30 C39 121.3(6) . . ?
C32 C30 H30 119.4 . . ?
C39 C30 H30 119.4 . . ?
O7 N1 O8 124.7(7) . . ?
O7 N1 C18 117.8(6) . . ?
O8 N1 C18 117.5(7) . . ?
C34 C31 C24 120.3(6) . . ?
C34 C31 H31 119.9 . . ?
C24 C31 H31 119.9 . . ?
C30 C32 C17 121.6(6) . . ?
C30 C32 H32 119.2 . . ?
C17 C32 H32 119.2 . . ?
C28 C33 C22 126.1(7) . . ?
C28 C33 H33 117.0 . . ?
C22 C33 H33 117.0 . . ?
C31 C34 C22 121.6(6) . . ?
C31 C34 H34 119.2 . . ?
C22 C34 H34 119.2 . . ?
C18 C35 C19 118.3(6) . . ?
C18 C35 H35 120.9 . . ?
C19 C35 H35 120.9 . . ?
C24 C36 C20 118.6(6) . . ?
C24 C36 H36 120.7 . . ?
C20 C36 H36 120.7 . . ?
C15 C37 C16 127.1(7) . . ?
C15 C37 H37 116.4 . . ?
C16 C37 H37 116.4 . . ?
C42 C38 C16 122.7(6) . . ?
C42 C38 H38 118.6 . . ?
C16 C38 H38 118.7 . . ?
C40 C39 C30 117.6(6) . . ?
C40 C39 H39 121.2 . . ?
C30 C39 H39 121.2 . . ?
C39 C40 C25 121.4(6) . . ?
C39 C40 H40 119.3 . . ?
C25 C40 H40 119.3 . . ?
C27 C41 C29 118.5(6) . . ?
C27 C41 H41 120.7 . . ?
C29 C41 H41 120.7 . . ?
C38 C42 C18 119.1(6) . . ?
C38 C42 H42 120.5 . . ?
C18 C42 H42 120.5 . . ?
C53 C43 C49 117.5(6) . . ?
C53 C43 C54 118.9(6) . . ?
C49 C43 C54 123.6(6) . . ?
C45 C44 C48 117.5(6) . . ?
C45 C44 C47 125.9(6) . . ?
C48 C44 C47 116.6(6) . . ?
C52 C45 C44 121.9(6) . . ?
C52 C45 H45 119.0 . . ?
C44 C45 H45 119.0 . . ?
C51 C46 C55 121.0(6) . . ?
C51 C46 N4 118.6(6) . . ?
C55 C46 N4 120.3(6) . . ?
O6 N4 O5 123.3(7) . . ?
O6 N4 C46 119.6(7) . . ?
O5 N4 C46 117.1(6) . . ?
C54 C47 C44 126.3(7) . . ?
C54 C47 H47 116.8 . . ?
C44 C47 H47 116.8 . . ?
C50 C48 C44 120.6(6) . . ?
C50 C48 H48 119.7 . . ?
C44 C48 H48 119.7 . . ?
C43 C49 C55 120.2(6) . . ?
C43 C49 H49 119.9 . . ?
C55 C49 H49 119.9 . . ?
C56 C50 C48 120.6(6) . . ?
C56 C50 H50 119.7 . . ?
C48 C50 H50 119.7 . . ?
C53 C51 C46 119.5(6) . . ?
C53 C51 H51 120.2 . . ?
C46 C51 H51 120.2 . . ?
C45 C52 C56 120.2(6) . . ?
C45 C52 H52 119.9 . . ?
C56 C52 H52 119.9 . . ?
C51 C53 C43 122.7(6) . . ?
C51 C53 H53 118.7 . . ?
C43 C53 H53 118.7 . . ?
C47 C54 C43 126.5(7) . . ?
C47 C54 H54 116.7 . . ?
C43 C54 H54 116.7 . . ?
C46 C55 C49 119.0(6) . . ?
C46 C55 H55 120.5 . . ?
C49 C55 H55 120.5 . . ?
C50 C56 C52 119.2(6) . . ?
C50 C56 H56 120.4 . . ?
C52 C56 H56 120.4 . . ?

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
C13 C1 C2 C11 -1.9(8) . . . . ?
C13 C1 C2 C12 176.2(5) . . . . ?
C10 C4 N3 O4 4.0(9) . . . . ?
C13 C4 N3 O4 -176.4(6) . . . . ?
C10 C4 N3 O3 -174.9(6) . . . . ?
C13 C4 N3 O3 4.6(9) . . . . ?
C6 C3 C5 C7 1.6(8) . . . . ?
C8 C3 C5 C7 -179.0(5) . . . . ?
C5 C3 C6 C9 -1.2(8) . . . . ?
C8 C3 C6 C9 179.4(5) . . . . ?
C3 C5 C7 C14 -0.7(9) . . . . ?
C6 C3 C8 C12 1.6(9) . . . . ?
C5 C3 C8 C12 -177.8(6) . . . . ?
C3 C6 C9 C14 -0.1(9) . . . . ?
C13 C4 C10 C11 -1.4(9) . . . . ?
N3 C4 C10 C11 178.1(5) . . . . ?
C4 C10 C11 C2 0.1(10) . . . . ?
C1 C2 C11 C10 1.5(9) . . . . ?
C12 C2 C11 C10 -176.7(5) . . . . ?
C3 C8 C12 C2 -178.4(5) . . . . ?
C1 C2 C12 C8 -8.1(9) . . . . ?
C11 C2 C12 C8 170.0(6) . . . . ?
C2 C1 C13 C4 0.7(9) . . . . ?
C10 C4 C13 C1 1.0(9) . . . . ?
N3 C4 C13 C1 -178.5(5) . . . . ?
C5 C7 C14 C9 -0.6(9) . . . . ?
C6 C9 C14 C7 1.0(9) . . . . ?
C38 C16 C19 C35 -0.3(8) . . . . ?
C37 C16 C19 C35 176.7(5) . . . . ?
C37 C15 C21 C23 -177.3(6) . . . . ?
C37 C15 C21 C26 2.8(9) . . . . ?
C36 C20 C22 C34 1.7(8) . . . . ?
C36 C20 C22 C33 -176.3(5) . . . . ?
C26 C21 C23 C29 1.2(8) . . . . ?
C15 C21 C23 C29 -178.7(5) . . . . ?
C32 C17 C25 C40 0.5(8) . . . . ?
C28 C17 C25 C40 178.9(5) . . . . ?
C23 C21 C26 C27 -1.5(8) . . . . ?
C15 C21 C26 C27 178.4(5) . . . . ?
C31 C24 N2 O1 175.2(6) . . . . ?
C36 C24 N2 O1 -2.6(9) . . . . ?
C31 C24 N2 O2 -5.7(8) . . . . ?
C36 C24 N2 O2 176.5(5) . . . . ?
C21 C26 C27 C41 1.4(9) . . . . ?
C32 C17 C28 C33 -3.5(10) . . . . ?
C25 C17 C28 C33 178.3(6) . . . . ?
C21 C23 C29 C41 -0.8(8) . . . . ?
C42 C18 N1 O7 -175.3(6) . . . . ?
C35 C18 N1 O7 3.6(9) . . . . ?
C42 C18 N1 O8 4.3(8) . . . . ?
C35 C18 N1 O8 -176.8(5) . . . . ?
C36 C24 C31 C34 0.9(9) . . . . ?
N2 C24 C31 C34 -176.9(5) . . . . ?
C39 C30 C32 C17 0.9(9) . . . . ?
C25 C17 C32 C30 -0.6(8) . . . . ?
C28 C17 C32 C30 -178.7(5) . . . . ?
C17 C28 C33 C22 179.0(5) . . . . ?
C34 C22 C33 C28 -169.5(6) . . . . ?
C20 C22 C33 C28 8.5(10) . . . . ?
C24 C31 C34 C22 -0.3(9) . . . . ?
C20 C22 C34 C31 -0.9(9) . . . . ?
C33 C22 C34 C31 177.2(5) . . . . ?
C42 C18 C35 C19 1.5(8) . . . . ?
N1 C18 C35 C19 -177.3(5) . . . . ?
C16 C19 C35 C18 -0.6(8) . . . . ?
C31 C24 C36 C20 -0.1(9) . . . . ?
N2 C24 C36 C20 177.6(5) . . . . ?
C22 C20 C36 C24 -1.2(9) . . . . ?
C21 C15 C37 C16 -179.0(5) . . . . ?
C19 C16 C37 C15 -7.8(10) . . . . ?
C38 C16 C37 C15 169.1(6) . . . . ?
C19 C16 C38 C42 0.4(9) . . . . ?
C37 C16 C38 C42 -176.7(5) . . . . ?
C32 C30 C39 C40 -1.1(9) . . . . ?
C30 C39 C40 C25 1.1(9) . . . . ?
C17 C25 C40 C39 -0.8(9) . . . . ?
C26 C27 C41 C29 -1.0(9) . . . . ?
C23 C29 C41 C27 0.7(8) . . . . ?
C16 C38 C42 C18 0.4(9) . . . . ?
C35 C18 C42 C38 -1.4(9) . . . . ?
N1 C18 C42 C38 177.4(5) . . . . ?
C48 C44 C45 C52 -0.1(8) . . . . ?
C47 C44 C45 C52 -178.8(5) . . . . ?
C51 C46 N4 O6 -6.3(8) . . . . ?
C55 C46 N4 O6 176.5(5) . . . . ?
C51 C46 N4 O5 175.4(6) . . . . ?
C55 C46 N4 O5 -1.8(8) . . . . ?
C45 C44 C47 C54 -3.3(9) . . . . ?
C48 C44 C47 C54 178.1(6) . . . . ?
C45 C44 C48 C50 0.3(8) . . . . ?
C47 C44 C48 C50 179.0(5) . . . . ?
C53 C43 C49 C55 2.4(8) . . . . ?
C54 C43 C49 C55 -175.9(5) . . . . ?
C44 C48 C50 C56 -0.3(8) . . . . ?
C55 C46 C51 C53 -1.2(9) . . . . ?
N4 C46 C51 C53 -178.4(5) . . . . ?
C44 C45 C52 C56 0.0(9) . . . . ?
C46 C51 C53 C43 2.5(9) . . . . ?
C49 C43 C53 C51 -3.1(9) . . . . ?
C54 C43 C53 C51 175.3(5) . . . . ?
C44 C47 C54 C43 179.0(5) . . . . ?
C53 C43 C54 C47 -170.1(6) . . . . ?
C49 C43 C54 C47 8.1(9) . . . . ?
C51 C46 C55 C49 0.5(8) . . . . ?
N4 C46 C55 C49 177.7(5) . . . . ?
C43 C49 C55 C46 -1.2(8) . . . . ?
C48 C50 C56 C52 0.2(8) . . . . ?
C45 C52 C56 C50 -0.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate-Hexane'
