# 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 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 949747'
_audit_update_record             
;
2013-07-10 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(3-(3-cyano-6-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)propoxy)-4-methyl-6-phenylnicotinonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          194-195
_chemical_formula_moiety         'C29 H24 N4 O2'
_chemical_formula_sum            'C29 H24 N4 O2'
_chemical_formula_weight         460.52

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   15.270(4)
_cell_length_b                   9.4879(19)
_cell_length_c                   33.952(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4918.9(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlisPro

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15186
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.1225
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         29.11
_reflns_number_total             5720
_reflns_number_gt                2957
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0942P)²+0.4721P] 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         5720
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2383
_refine_ls_wR_factor_gt          0.1839
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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
H12C H 0.477(2) 0.527(3) -0.0740(8) 0.055(8) Uiso 1 1 d . . .
H12A H 0.555(2) 0.523(4) -0.0404(12) 0.084(11) Uiso 1 1 d . . .
H12B H 0.557(3) 0.642(4) -0.0751(12) 0.103(14) Uiso 1 1 d . . .
O2 O 0.66530(11) 0.6336(2) 0.01719(6) 0.0496(5) Uani 1 1 d . . .
N3 N 0.71903(14) 0.7333(2) 0.07414(6) 0.0475(6) Uani 1 1 d . . .
C24 C 0.65719(16) 0.7239(3) 0.04780(8) 0.0418(6) Uani 1 1 d . . .
N1 N 0.68344(14) 0.4493(2) -0.08982(7) 0.0485(6) Uani 1 1 d . . .
O1 O 0.81687(13) 0.3597(2) -0.10554(7) 0.0704(7) Uani 1 1 d . . .
C23 C 0.57930(16) 0.8029(3) 0.04860(8) 0.0479(7) Uani 1 1 d . . .
C20 C 0.70712(19) 0.8259(3) 0.10420(8) 0.0500(7) Uani 1 1 d . . .
C21 C 0.6326(2) 0.9065(3) 0.10727(8) 0.0560(8) Uani 1 1 d . . .
H21 H 0.6261 0.9674 0.1285 0.067 Uiso 1 1 calc R . .
C26 C 0.51426(18) 0.7856(3) 0.01907(10) 0.0567(8) Uani 1 1 d . . .
C10 C 0.73829(19) 0.3625(3) -0.11250(9) 0.0540(7) Uani 1 1 d . . .
C7 C 0.60667(18) 0.2821(3) -0.14802(8) 0.0493(7) Uani 1 1 d . . .
C11 C 0.69605(19) 0.2819(3) -0.14304(8) 0.0524(7) Uani 1 1 d . . .
C22 C 0.56730(18) 0.8986(3) 0.07934(9) 0.0529(7) Uani 1 1 d . . .
C19 C 0.7789(2) 0.8359(3) 0.13290(8) 0.0566(8) Uani 1 1 d . . .
C9 C 0.59452(19) 0.4515(3) -0.09498(9) 0.0515(7) Uani 1 1 d . . .
C27 C 0.74606(17) 0.5543(3) 0.01406(9) 0.0510(7) Uani 1 1 d . . .
H27A H 0.7566 0.5010 0.0380 0.061 Uiso 1 1 calc R . .
H27B H 0.7952 0.6172 0.0097 0.061 Uiso 1 1 calc R . .
C28 C 0.73429(19) 0.4562(3) -0.02063(8) 0.0522(7) Uani 1 1 d . . .
H28A H 0.7845 0.3938 -0.0223 0.063 Uiso 1 1 calc R . .
H28B H 0.6827 0.3985 -0.0164 0.063 Uiso 1 1 calc R . .
C29 C 0.72463(19) 0.5351(3) -0.05905(8) 0.0516(7) Uani 1 1 d . . .
H29A H 0.6895 0.6189 -0.0547 0.062 Uiso 1 1 calc R . .
H29B H 0.7820 0.5652 -0.0680 0.062 Uiso 1 1 calc R . .
C6 C 0.56072(19) 0.1921(3) -0.17717(8) 0.0513(7) Uani 1 1 d . . .
C8 C 0.55709(18) 0.3698(3) -0.12298(9) 0.0525(7) Uani 1 1 d . . .
H8 H 0.4965 0.3715 -0.1258 0.063 Uiso 1 1 calc R . .
N4 N 0.46026(19) 0.7729(3) -0.00390(9) 0.0787(9) Uani 1 1 d . . .
C1 C 0.4867(2) 0.2428(4) -0.19641(9) 0.0625(8) Uani 1 1 d . . .
H1 H 0.4686 0.3352 -0.1922 0.075 Uiso 1 1 calc R . .
C13 C 0.7559(2) 0.2056(4) -0.16759(10) 0.0674(9) Uani 1 1 d . . .
C12 C 0.5410(3) 0.5438(4) -0.06841(12) 0.0673(9) Uani 1 1 d . . .
C25 C 0.4866(2) 0.9878(4) 0.08188(11) 0.0728(10) Uani 1 1 d . . .
H25A H 0.4900 1.0473 0.1047 0.109 Uiso 1 1 calc R . .
H25B H 0.4360 0.9282 0.0839 0.109 Uiso 1 1 calc R . .
H25C H 0.4819 1.0451 0.0587 0.109 Uiso 1 1 calc R . .
C5 C 0.5854(2) 0.0521(3) -0.18392(9) 0.0609(8) Uani 1 1 d . . .
H5 H 0.6346 0.0158 -0.1713 0.073 Uiso 1 1 calc R . .
C2 C 0.4400(2) 0.1574(4) -0.22171(9) 0.0733(10) Uani 1 1 d . . .
H2 H 0.3913 0.1929 -0.2348 0.088 Uiso 1 1 calc R . .
C3 C 0.4653(3) 0.0190(5) -0.22761(10) 0.0809(11) Uani 1 1 d . . .
H3 H 0.4330 -0.0390 -0.2443 0.097 Uiso 1 1 calc R . .
C14 C 0.8620(2) 0.7878(3) 0.12359(10) 0.0649(9) Uani 1 1 d . . .
H14 H 0.8717 0.7473 0.0990 0.078 Uiso 1 1 calc R . .
C4 C 0.5380(3) -0.0323(4) -0.20890(10) 0.0746(10) Uani 1 1 d . . .
H4 H 0.5555 -0.1249 -0.2131 0.090 Uiso 1 1 calc R . .
C15 C 0.9299(3) 0.7984(4) 0.14948(12) 0.0864(12) Uani 1 1 d . . .
H15 H 0.9853 0.7670 0.1423 0.104 Uiso 1 1 calc R . .
N2 N 0.8052(2) 0.1488(4) -0.18724(11) 0.1005(11) Uani 1 1 d . . .
C16 C 0.9164(3) 0.8552(4) 0.18599(13) 0.0948(14) Uani 1 1 d . . .
H16 H 0.9625 0.8618 0.2038 0.114 Uiso 1 1 calc R . .
C18 C 0.7673(3) 0.8947(5) 0.16991(11) 0.0998(14) Uani 1 1 d . . .
H18 H 0.7126 0.9296 0.1770 0.120 Uiso 1 1 calc R . .
C17 C 0.8352(3) 0.9020(6) 0.19614(13) 0.1169(17) Uani 1 1 d . . .
H17 H 0.8258 0.9392 0.2211 0.140 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
O2 C24 1.352(3) . ?
O2 C27 1.448(3) . ?
N3 C24 1.304(3) . ?
N3 C20 1.359(3) . ?
C24 C23 1.406(4) . ?
N1 C9 1.369(3) . ?
N1 C10 1.404(4) . ?
N1 C29 1.467(3) . ?
O1 C10 1.223(3) . ?
C23 C22 1.395(4) . ?
C23 C26 1.421(4) . ?
C20 C21 1.376(4) . ?
C20 C19 1.470(4) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C26 N4 1.141(4) . ?
C10 C11 1.441(4) . ?
C7 C11 1.375(4) . ?
C7 C8 1.410(4) . ?
C7 C6 1.484(4) . ?
C11 C13 1.433(4) . ?
C22 C25 1.498(4) . ?
C19 C14 1.385(4) . ?
C19 C18 1.386(4) . ?
C9 C8 1.354(4) . ?
C9 C12 1.499(4) . ?
C27 C28 1.512(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.512(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C6 C1 1.391(4) . ?
C6 C5 1.400(4) . ?
C8 H8 0.9300 . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C13 N2 1.142(4) . ?
C12 H12C 1.00(3) . ?
C12 H12A 0.99(4) . ?
C12 H12B 0.99(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C5 C4 1.373(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C15 C16 1.367(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(6) . ?
C16 H16 0.9300 . ?
C18 C17 1.368(6) . ?
C18 H18 0.9300 . ?
C17 H17 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
C24 O2 C27 117.6(2) . . ?
C24 N3 C20 117.6(2) . . ?
N3 C24 O2 120.3(2) . . ?
N3 C24 C23 124.2(2) . . ?
O2 C24 C23 115.5(2) . . ?
C9 N1 C10 122.0(2) . . ?
C9 N1 C29 120.5(2) . . ?
C10 N1 C29 117.4(2) . . ?
C22 C23 C24 118.2(2) . . ?
C22 C23 C26 120.7(2) . . ?
C24 C23 C26 121.1(3) . . ?
N3 C20 C21 121.8(3) . . ?
N3 C20 C19 116.1(3) . . ?
C21 C20 C19 122.1(3) . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
N4 C26 C23 178.1(3) . . ?
O1 C10 N1 119.5(3) . . ?
O1 C10 C11 124.5(3) . . ?
N1 C10 C11 116.0(3) . . ?
C11 C7 C8 117.4(3) . . ?
C11 C7 C6 123.4(3) . . ?
C8 C7 C6 119.2(3) . . ?
C7 C11 C13 124.2(3) . . ?
C7 C11 C10 122.1(3) . . ?
C13 C11 C10 113.7(3) . . ?
C21 C22 C23 117.1(3) . . ?
C21 C22 C25 121.6(3) . . ?
C23 C22 C25 121.3(3) . . ?
C14 C19 C18 117.2(3) . . ?
C14 C19 C20 120.7(3) . . ?
C18 C19 C20 122.1(3) . . ?
C8 C9 N1 120.0(3) . . ?
C8 C9 C12 121.8(3) . . ?
N1 C9 C12 118.2(3) . . ?
O2 C27 C28 106.0(2) . . ?
O2 C27 H27A 110.5 . . ?
C28 C27 H27A 110.5 . . ?
O2 C27 H27B 110.5 . . ?
C28 C27 H27B 110.5 . . ?
H27A C27 H27B 108.7 . . ?
C29 C28 C27 112.2(2) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
N1 C29 C28 112.4(2) . . ?
N1 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
N1 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 119.9(3) . . ?
C5 C6 C7 121.9(3) . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
N2 C13 C11 177.7(4) . . ?
C9 C12 H12C 108.7(16) . . ?
C9 C12 H12A 110(2) . . ?
H12C C12 H12A 111(3) . . ?
C9 C12 H12B 106(2) . . ?
H12C C12 H12B 110(3) . . ?
H12A C12 H12B 111(3) . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C15 C14 C19 121.7(3) . . ?
C15 C14 H14 119.1 . . ?
C19 C14 H14 119.1 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?

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
C20 N3 C24 O2 180.0(2) . . . . ?
C20 N3 C24 C23 -0.1(4) . . . . ?
C27 O2 C24 N3 -2.8(3) . . . . ?
C27 O2 C24 C23 177.3(2) . . . . ?
N3 C24 C23 C22 0.5(4) . . . . ?
O2 C24 C23 C22 -179.6(2) . . . . ?
N3 C24 C23 C26 -179.2(3) . . . . ?
O2 C24 C23 C26 0.7(4) . . . . ?
C24 N3 C20 C21 0.6(4) . . . . ?
C24 N3 C20 C19 -178.8(2) . . . . ?
N3 C20 C21 C22 -1.4(4) . . . . ?
C19 C20 C21 C22 177.9(3) . . . . ?
C22 C23 C26 N4 -28(11) . . . . ?
C24 C23 C26 N4 152(11) . . . . ?
C9 N1 C10 O1 -176.7(3) . . . . ?
C29 N1 C10 O1 1.2(4) . . . . ?
C9 N1 C10 C11 3.4(4) . . . . ?
C29 N1 C10 C11 -178.7(2) . . . . ?
C8 C7 C11 C13 -176.0(3) . . . . ?
C6 C7 C11 C13 6.0(5) . . . . ?
C8 C7 C11 C10 2.7(4) . . . . ?
C6 C7 C11 C10 -175.2(3) . . . . ?
O1 C10 C11 C7 175.8(3) . . . . ?
N1 C10 C11 C7 -4.4(4) . . . . ?
O1 C10 C11 C13 -5.4(4) . . . . ?
N1 C10 C11 C13 174.5(3) . . . . ?
C20 C21 C22 C23 1.6(4) . . . . ?
C20 C21 C22 C25 -178.8(3) . . . . ?
C24 C23 C22 C21 -1.2(4) . . . . ?
C26 C23 C22 C21 178.5(3) . . . . ?
C24 C23 C22 C25 179.2(3) . . . . ?
C26 C23 C22 C25 -1.1(4) . . . . ?
N3 C20 C19 C14 18.6(4) . . . . ?
C21 C20 C19 C14 -160.7(3) . . . . ?
N3 C20 C19 C18 -162.2(3) . . . . ?
C21 C20 C19 C18 18.5(5) . . . . ?
C10 N1 C9 C8 -0.9(4) . . . . ?
C29 N1 C9 C8 -178.8(2) . . . . ?
C10 N1 C9 C12 177.9(3) . . . . ?
C29 N1 C9 C12 0.0(4) . . . . ?
C24 O2 C27 C28 176.1(2) . . . . ?
O2 C27 C28 C29 64.6(3) . . . . ?
C9 N1 C29 C28 91.5(3) . . . . ?
C10 N1 C29 C28 -86.5(3) . . . . ?
C27 C28 C29 N1 -159.9(2) . . . . ?
C11 C7 C6 C1 -144.6(3) . . . . ?
C8 C7 C6 C1 37.5(4) . . . . ?
C11 C7 C6 C5 40.5(4) . . . . ?
C8 C7 C6 C5 -137.4(3) . . . . ?
N1 C9 C8 C7 -1.0(4) . . . . ?
C12 C9 C8 C7 -179.7(3) . . . . ?
C11 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C9 178.1(3) . . . . ?
C5 C6 C1 C2 -0.7(4) . . . . ?
C7 C6 C1 C2 -175.8(3) . . . . ?
C7 C11 C13 N2 132(10) . . . . ?
C10 C11 C13 N2 -46(10) . . . . ?
C1 C6 C5 C4 0.2(4) . . . . ?
C7 C6 C5 C4 175.2(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C18 C19 C14 C15 -0.4(5) . . . . ?
C20 C19 C14 C15 178.8(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C6 C5 C4 C3 -0.2(5) . . . . ?
C19 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C14 C19 C18 C17 -1.1(6) . . . . ?
C20 C19 C18 C17 179.7(4) . . . . ?
C15 C16 C17 C18 -1.0(8) . . . . ?
C19 C18 C17 C16 1.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 25.24
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 25.24
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 949921'
_audit_update_record             
;
2013-07-11 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(3-(3-cyano-6-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)propoxy)-4-methyl-6-phenylnicotinonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H24 N4 O2'
_chemical_formula_sum            'C29 H24 N4 O2'
_chemical_formula_weight         460.52

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   'P 21/n'

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                   7.2217(6)
_cell_length_b                   14.0412(13)
_cell_length_c                   24.134(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.641(9)
_cell_angle_gamma                90.00
_cell_volume                     2435.4(4)
_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            yellow
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CrysAlisPro

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11552
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.04
_reflns_number_total             5549
_reflns_number_gt                3437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0547P)²+0.5265P] 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         5549
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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
H12A H -0.405(3) -0.0027(18) -0.0647(9) 0.068(7) Uiso 1 1 d . . .
H12C H -0.249(3) 0.0693(18) -0.0334(11) 0.085(8) Uiso 1 1 d . . .
H12B H -0.375(3) 0.101(2) -0.0869(11) 0.084(9) Uiso 1 1 d . . .
N3 N 0.07865(19) 0.39309(12) 0.05521(6) 0.0430(4) Uani 1 1 d . . .
O2 O -0.01253(18) 0.24478(10) 0.02178(6) 0.0556(4) Uani 1 1 d . . .
N1 N -0.0234(2) 0.06609(11) -0.11705(7) 0.0436(4) Uani 1 1 d . . .
C7 C -0.0802(2) -0.10707(13) -0.17308(7) 0.0390(4) Uani 1 1 d . . .
C24 C -0.0419(2) 0.32298(14) 0.05199(8) 0.0432(5) Uani 1 1 d . . .
C6 C -0.1213(3) -0.19846(13) -0.20226(7) 0.0417(4) Uani 1 1 d . . .
C23 C -0.2057(2) 0.32256(15) 0.07887(8) 0.0437(5) Uani 1 1 d . . .
C10 C 0.1084(3) 0.03846(14) -0.15282(8) 0.0460(5) Uani 1 1 d . . .
C20 C 0.0404(2) 0.47035(14) 0.08593(7) 0.0408(4) Uani 1 1 d . . .
O1 O 0.2424(2) 0.09010(11) -0.15863(7) 0.0665(4) Uani 1 1 d . . .
C19 C 0.1839(2) 0.54582(13) 0.09029(7) 0.0399(4) Uani 1 1 d . . .
C22 C -0.2475(2) 0.40221(15) 0.10924(8) 0.0453(5) Uani 1 1 d . . .
C8 C -0.2004(3) -0.07364(14) -0.13482(8) 0.0444(5) Uani 1 1 d . . .
H8 H -0.3012 -0.1112 -0.1274 0.053 Uiso 1 1 calc R . .
C9 C -0.1748(2) 0.01145(13) -0.10826(8) 0.0423(4) Uani 1 1 d . . .
C21 C -0.1221(2) 0.47693(15) 0.11199(8) 0.0461(5) Uani 1 1 d . . .
H21 H -0.1468 0.5319 0.1314 0.055 Uiso 1 1 calc R . .
C14 C 0.2994(2) 0.55705(15) 0.04802(8) 0.0465(5) Uani 1 1 d . . .
H14 H 0.2817 0.5195 0.0162 0.056 Uiso 1 1 calc R . .
C27 C 0.1589(3) 0.24013(16) -0.00385(10) 0.0584(6) Uani 1 1 d . . .
H27A H 0.2646 0.2388 0.0242 0.070 Uiso 1 1 calc R . .
H27B H 0.1710 0.2948 -0.0278 0.070 Uiso 1 1 calc R . .
C26 C -0.3206(3) 0.23930(17) 0.07479(9) 0.0554(6) Uani 1 1 d . . .
C11 C 0.0701(2) -0.05000(13) -0.18190(8) 0.0418(4) Uani 1 1 d . . .
C29 C 0.0120(3) 0.15860(14) -0.08872(9) 0.0516(5) Uani 1 1 d . . .
H29A H -0.1043 0.1840 -0.0781 0.062 Uiso 1 1 calc R . .
H29B H 0.0606 0.2032 -0.1144 0.062 Uiso 1 1 calc R . .
C16 C 0.4706(3) 0.67880(15) 0.10023(10) 0.0570(6) Uani 1 1 d . . .
H16 H 0.5672 0.7228 0.1037 0.068 Uiso 1 1 calc R . .
C1 C -0.3043(3) -0.22120(16) -0.22115(8) 0.0528(5) Uani 1 1 d . . .
H1 H -0.3995 -0.1787 -0.2156 0.063 Uiso 1 1 calc R . .
C13 C 0.1955(3) -0.07153(15) -0.22268(9) 0.0503(5) Uani 1 1 d . . .
C5 C 0.0171(3) -0.26336(14) -0.21118(8) 0.0513(5) Uani 1 1 d . . .
H5 H 0.1404 -0.2491 -0.1992 0.062 Uiso 1 1 calc R . .
C18 C 0.2140(3) 0.60270(15) 0.13738(9) 0.0515(5) Uani 1 1 d . . .
H18 H 0.1370 0.5965 0.1659 0.062 Uiso 1 1 calc R . .
C28 C 0.1491(3) 0.14930(16) -0.03741(9) 0.0561(6) Uani 1 1 d . . .
H28A H 0.1114 0.0973 -0.0146 0.067 Uiso 1 1 calc R . .
H28B H 0.2713 0.1345 -0.0485 0.067 Uiso 1 1 calc R . .
N2 N 0.2953(3) -0.08517(15) -0.25597(9) 0.0754(6) Uani 1 1 d . . .
C15 C 0.4408(3) 0.62386(16) 0.05312(9) 0.0543(5) Uani 1 1 d . . .
H15 H 0.5163 0.6317 0.0244 0.065 Uiso 1 1 calc R . .
C17 C 0.3567(3) 0.66830(16) 0.14233(9) 0.0587(6) Uani 1 1 d . . .
H17 H 0.3761 0.7056 0.1742 0.070 Uiso 1 1 calc R . .
C2 C -0.3454(3) -0.30683(19) -0.24809(9) 0.0656(7) Uani 1 1 d . . .
H2 H -0.4677 -0.3210 -0.2612 0.079 Uiso 1 1 calc R . .
C12 C -0.3111(4) 0.04738(19) -0.07046(13) 0.0616(6) Uani 1 1 d . . .
C4 C -0.0253(4) -0.34908(16) -0.23761(9) 0.0653(6) Uani 1 1 d . . .
H4 H 0.0691 -0.3920 -0.2432 0.078 Uiso 1 1 calc R . .
C25 C -0.4192(3) 0.40626(18) 0.13955(10) 0.0657(7) Uani 1 1 d . . .
H25A H -0.4891 0.3485 0.1329 0.099 Uiso 1 1 calc R . .
H25B H -0.4941 0.4596 0.1263 0.099 Uiso 1 1 calc R . .
H25C H -0.3841 0.4132 0.1787 0.099 Uiso 1 1 calc R . .
N4 N -0.4122(3) 0.17317(17) 0.07212(11) 0.0870(7) Uani 1 1 d . . .
C3 C -0.2066(4) -0.37095(18) -0.25557(10) 0.0696(7) Uani 1 1 d . . .
H3 H -0.2353 -0.4291 -0.2728 0.084 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
N3 C24 1.311(2) . ?
N3 C20 1.358(2) . ?
O2 C24 1.346(2) . ?
O2 C27 1.439(2) . ?
N1 C9 1.369(2) . ?
N1 C10 1.401(2) . ?
N1 C29 1.479(2) . ?
C7 C11 1.383(2) . ?
C7 C8 1.408(2) . ?
C7 C6 1.480(3) . ?
C24 C23 1.404(2) . ?
C6 C5 1.385(3) . ?
C6 C1 1.392(3) . ?
C23 C22 1.386(3) . ?
C23 C26 1.431(3) . ?
C10 O1 1.229(2) . ?
C10 C11 1.440(3) . ?
C20 C21 1.388(2) . ?
C20 C19 1.479(2) . ?
C19 C18 1.388(3) . ?
C19 C14 1.389(2) . ?
C22 C21 1.383(3) . ?
C22 C25 1.501(3) . ?
C8 C9 1.360(3) . ?
C8 H8 0.9300 . ?
C9 C12 1.494(3) . ?
C21 H21 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C27 C28 1.509(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 N4 1.138(3) . ?
C11 C13 1.433(3) . ?
C29 C28 1.513(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C16 C15 1.373(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C13 N2 1.147(2) . ?
C5 C4 1.382(3) . ?
C5 H5 0.9300 . ?
C18 C17 1.379(3) . ?
C18 H18 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C12 H12A 1.00(2) . ?
C12 H12C 1.01(3) . ?
C12 H12B 0.95(3) . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C3 H3 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
C24 N3 C20 117.56(15) . . ?
C24 O2 C27 117.24(14) . . ?
C9 N1 C10 122.79(16) . . ?
C9 N1 C29 121.67(16) . . ?
C10 N1 C29 115.54(15) . . ?
C11 C7 C8 116.85(17) . . ?
C11 C7 C6 123.56(16) . . ?
C8 C7 C6 119.57(16) . . ?
N3 C24 O2 120.36(16) . . ?
N3 C24 C23 124.08(18) . . ?
O2 C24 C23 115.56(16) . . ?
C5 C6 C1 118.34(19) . . ?
C5 C6 C7 122.06(17) . . ?
C1 C6 C7 119.60(17) . . ?
C22 C23 C24 118.55(17) . . ?
C22 C23 C26 122.72(17) . . ?
C24 C23 C26 118.73(19) . . ?
O1 C10 N1 119.84(18) . . ?
O1 C10 C11 124.67(18) . . ?
N1 C10 C11 115.46(16) . . ?
N3 C20 C21 121.82(17) . . ?
N3 C20 C19 115.64(15) . . ?
C21 C20 C19 122.54(17) . . ?
C18 C19 C14 118.60(17) . . ?
C18 C19 C20 121.52(16) . . ?
C14 C19 C20 119.78(17) . . ?
C21 C22 C23 117.50(16) . . ?
C21 C22 C25 121.07(19) . . ?
C23 C22 C25 121.41(18) . . ?
C9 C8 C7 122.52(17) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 N1 119.53(16) . . ?
C8 C9 C12 121.14(18) . . ?
N1 C9 C12 119.32(18) . . ?
C22 C21 C20 120.43(19) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C15 C14 C19 120.22(18) . . ?
C15 C14 H14 119.9 . . ?
C19 C14 H14 119.9 . . ?
O2 C27 C28 105.78(16) . . ?
O2 C27 H27A 110.6 . . ?
C28 C27 H27A 110.6 . . ?
O2 C27 H27B 110.6 . . ?
C28 C27 H27B 110.6 . . ?
H27A C27 H27B 108.7 . . ?
N4 C26 C23 179.3(3) . . ?
C7 C11 C13 122.82(18) . . ?
C7 C11 C10 122.73(16) . . ?
C13 C11 C10 114.38(16) . . ?
N1 C29 C28 111.85(16) . . ?
N1 C29 H29A 109.2 . . ?
C28 C29 H29A 109.2 . . ?
N1 C29 H29B 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C15 C16 C17 119.64(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
N2 C13 C11 177.4(2) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C17 C18 C19 120.72(19) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C27 C28 C29 111.04(18) . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28B 109.4 . . ?
C29 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C16 C15 C14 120.60(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 C12 H12A 110.2(13) . . ?
C9 C12 H12C 112.7(14) . . ?
H12A C12 H12C 109.8(19) . . ?
C9 C12 H12B 109.4(15) . . ?
H12A C12 H12B 108.1(19) . . ?
H12C C12 H12B 106(2) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?

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
C20 N3 C24 O2 179.44(17) . . . . ?
C20 N3 C24 C23 -0.9(3) . . . . ?
C27 O2 C24 N3 3.1(3) . . . . ?
C27 O2 C24 C23 -176.59(17) . . . . ?
C11 C7 C6 C5 41.9(3) . . . . ?
C8 C7 C6 C5 -139.42(19) . . . . ?
C11 C7 C6 C1 -138.67(19) . . . . ?
C8 C7 C6 C1 40.0(2) . . . . ?
N3 C24 C23 C22 2.4(3) . . . . ?
O2 C24 C23 C22 -177.96(17) . . . . ?
N3 C24 C23 C26 -176.34(18) . . . . ?
O2 C24 C23 C26 3.3(3) . . . . ?
C9 N1 C10 O1 -179.31(18) . . . . ?
C29 N1 C10 O1 0.3(3) . . . . ?
C9 N1 C10 C11 2.6(3) . . . . ?
C29 N1 C10 C11 -177.86(16) . . . . ?
C24 N3 C20 C21 -1.7(3) . . . . ?
C24 N3 C20 C19 177.55(16) . . . . ?
N3 C20 C19 C18 -148.66(18) . . . . ?
C21 C20 C19 C18 30.5(3) . . . . ?
N3 C20 C19 C14 27.4(2) . . . . ?
C21 C20 C19 C14 -153.36(18) . . . . ?
C24 C23 C22 C21 -1.2(3) . . . . ?
C26 C23 C22 C21 177.44(18) . . . . ?
C24 C23 C22 C25 -179.32(18) . . . . ?
C26 C23 C22 C25 -0.7(3) . . . . ?
C11 C7 C8 C9 1.4(3) . . . . ?
C6 C7 C8 C9 -177.37(18) . . . . ?
C7 C8 C9 N1 -2.4(3) . . . . ?
C7 C8 C9 C12 176.4(2) . . . . ?
C10 N1 C9 C8 0.3(3) . . . . ?
C29 N1 C9 C8 -179.29(17) . . . . ?
C10 N1 C9 C12 -178.5(2) . . . . ?
C29 N1 C9 C12 1.9(3) . . . . ?
C23 C22 C21 C20 -1.2(3) . . . . ?
C25 C22 C21 C20 176.94(18) . . . . ?
N3 C20 C21 C22 2.7(3) . . . . ?
C19 C20 C21 C22 -176.42(17) . . . . ?
C18 C19 C14 C15 -0.2(3) . . . . ?
C20 C19 C14 C15 -176.39(18) . . . . ?
C24 O2 C27 C28 -176.57(17) . . . . ?
C22 C23 C26 N4 -41(21) . . . . ?
C24 C23 C26 N4 138(21) . . . . ?
C8 C7 C11 C13 -175.13(18) . . . . ?
C6 C7 C11 C13 3.6(3) . . . . ?
C8 C7 C11 C10 1.7(3) . . . . ?
C6 C7 C11 C10 -179.60(17) . . . . ?
O1 C10 C11 C7 178.41(19) . . . . ?
N1 C10 C11 C7 -3.6(3) . . . . ?
O1 C10 C11 C13 -4.5(3) . . . . ?
N1 C10 C11 C13 173.50(17) . . . . ?
C9 N1 C29 C28 97.1(2) . . . . ?
C10 N1 C29 C28 -82.5(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C7 C6 C1 C2 -179.41(18) . . . . ?
C7 C11 C13 N2 134(5) . . . . ?
C10 C11 C13 N2 -43(5) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C7 C6 C5 C4 178.75(18) . . . . ?
C14 C19 C18 C17 -0.6(3) . . . . ?
C20 C19 C18 C17 175.53(19) . . . . ?
O2 C27 C28 C29 72.4(2) . . . . ?
N1 C29 C28 C27 -170.43(16) . . . . ?
C17 C16 C15 C14 -1.1(3) . . . . ?
C19 C14 C15 C16 1.0(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C19 C18 C17 C16 0.6(3) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 25.24
_diffrn_reflns_theta_full        29.04
_diffrn_measured_fraction_theta_full 25.24
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.036
