# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 5,6-dimethyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          543.15
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26

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'
O O 0.0106 0.0060 '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'

_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                   7.4066(7)
_cell_length_b                   9.4392(12)
_cell_length_c                   9.7203(13)
_cell_angle_alpha                116.399(13)
_cell_angle_beta                 97.846(9)
_cell_angle_gamma                90.409(9)
_cell_volume                     601.24(12)
_cell_formula_units_Z            2
_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          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6568
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         32.58
_reflns_number_total             3913
_reflns_number_gt                2298
_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)+(0.0921P)²+0.1047P] 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         3913
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 0.2929(3) 0.8288(2) 0.0020(2) 0.0457(4) Uani 1 1 d . . .
H1 H 0.4050 0.8517 -0.0195 0.055 Uiso 1 1 calc R . .
C5 C 0.1173(2) 0.7793(3) 0.1666(2) 0.0526(5) Uani 1 1 d . . .
H5 H 0.1102 0.7674 0.2558 0.063 Uiso 1 1 calc R . .
C2 C 0.1342(3) 0.8104(3) -0.1007(2) 0.0567(5) Uani 1 1 d . . .
H2 H 0.1405 0.8199 -0.1912 0.068 Uiso 1 1 calc R . .
C4 C -0.0406(3) 0.7630(3) 0.0642(3) 0.0653(6) Uani 1 1 d . . .
H4 H -0.1533 0.7415 0.0858 0.078 Uiso 1 1 calc R . .
C3 C -0.0315(3) 0.7784(3) -0.0688(2) 0.0616(6) Uani 1 1 d . . .
H3 H -0.1378 0.7670 -0.1371 0.074 Uiso 1 1 calc R . .
C7 C 0.4592(2) 0.8309(2) 0.24217(18) 0.0338(3) Uani 1 1 d . . .
N1 N 0.79107(19) 0.86547(17) 0.41915(16) 0.0381(3) Uani 1 1 d . . .
C11 C 0.5638(2) 0.97420(19) 0.30871(17) 0.0324(3) Uani 1 1 d . . .
C10 C 0.7418(2) 0.99469(19) 0.39774(18) 0.0341(3) Uani 1 1 d . . .
O1 O 0.84764(16) 1.11662(15) 0.45114(15) 0.0461(3) Uani 1 1 d . . .
C8 C 0.5221(2) 0.7032(2) 0.2693(2) 0.0413(4) Uani 1 1 d . . .
C14 C 0.5022(2) 1.1109(2) 0.29562(19) 0.0377(4) Uani 1 1 d . . .
C6 C 0.2850(2) 0.8130(2) 0.13629(18) 0.0372(4) Uani 1 1 d . . .
C9 C 0.6896(2) 0.7245(2) 0.3597(2) 0.0405(4) Uani 1 1 d . . .
C13 C 0.7762(3) 0.6008(3) 0.3974(3) 0.0617(6) Uani 1 1 d . . .
H13A H 0.8928 0.6434 0.4616 0.093 Uiso 1 1 calc R . .
H13B H 0.7927 0.5104 0.3029 0.093 Uiso 1 1 calc R . .
H13C H 0.6987 0.5691 0.4519 0.093 Uiso 1 1 calc R . .
N2 N 0.4549(2) 1.2236(2) 0.2902(2) 0.0579(5) Uani 1 1 d . . .
C12 C 0.4123(3) 0.5452(3) 0.1999(3) 0.0707(7) Uani 1 1 d . . .
H12A H 0.2995 0.5500 0.1409 0.106 Uiso 1 1 calc R . .
H12B H 0.3866 0.5213 0.2818 0.106 Uiso 1 1 calc R . .
H12C H 0.4809 0.4640 0.1330 0.106 Uiso 1 1 calc R . .
H15 H 0.910(3) 0.876(3) 0.468(3) 0.066(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(2) . ?
C1 C6 1.387(2) . ?
C1 H1 0.9300 . ?
C5 C6 1.381(2) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.374(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C7 C11 1.385(2) . ?
C7 C8 1.413(2) . ?
C7 C6 1.494(2) . ?
N1 C9 1.361(2) . ?
N1 C10 1.370(2) . ?
N1 H15 0.92(3) . ?
C11 C14 1.424(2) . ?
C11 C10 1.435(2) . ?
C10 O1 1.2465(19) . ?
C8 C9 1.376(2) . ?
C8 C12 1.510(3) . ?
C14 N2 1.143(2) . ?
C9 C13 1.496(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 120.34(18) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C5 C4 120.13(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C2 C1 120.07(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C3 C2 119.96(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C11 C7 C8 119.95(14) . . ?
C11 C7 C6 118.60(14) . . ?
C8 C7 C6 121.38(14) . . ?
C9 N1 C10 125.59(14) . . ?
C9 N1 H15 120.6(15) . . ?
C10 N1 H15 113.3(15) . . ?
C7 C11 C14 122.70(13) . . ?
C7 C11 C10 121.72(14) . . ?
C14 C11 C10 115.58(14) . . ?
O1 C10 N1 120.98(14) . . ?
O1 C10 C11 124.76(15) . . ?
N1 C10 C11 114.25(14) . . ?
C9 C8 C7 118.41(15) . . ?
C9 C8 C12 119.77(17) . . ?
C7 C8 C12 121.82(16) . . ?
N2 C14 C11 177.72(18) . . ?
C5 C6 C1 119.09(15) . . ?
C5 C6 C7 122.30(15) . . ?
C1 C6 C7 118.61(15) . . ?
N1 C9 C8 119.94(15) . . ?
N1 C9 C13 115.14(16) . . ?
C8 C9 C13 124.90(17) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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) . . . . ?
C6 C5 C4 C3 0.7(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C8 C7 C11 C14 -175.16(15) . . . . ?
C6 C7 C11 C14 7.8(2) . . . . ?
C8 C7 C11 C10 4.0(2) . . . . ?
C6 C7 C11 C10 -173.11(15) . . . . ?
C9 N1 C10 O1 -176.71(16) . . . . ?
C9 N1 C10 C11 2.3(2) . . . . ?
C7 C11 C10 O1 174.68(15) . . . . ?
C14 C11 C10 O1 -6.1(2) . . . . ?
C7 C11 C10 N1 -4.3(2) . . . . ?
C14 C11 C10 N1 174.87(14) . . . . ?
C11 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C8 C9 175.67(16) . . . . ?
C11 C7 C8 C12 179.66(18) . . . . ?
C6 C7 C8 C12 -3.3(3) . . . . ?
C7 C11 C14 N2 136(5) . . . . ?
C10 C11 C14 N2 -43(5) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.68(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 178.97(17) . . . . ?
C11 C7 C6 C5 -119.8(2) . . . . ?
C8 C7 C6 C5 63.1(2) . . . . ?
C11 C7 C6 C1 61.1(2) . . . . ?
C8 C7 C6 C1 -115.98(19) . . . . ?
C10 N1 C9 C8 0.1(3) . . . . ?
C10 N1 C9 C13 178.73(17) . . . . ?
C7 C8 C9 N1 -0.7(3) . . . . ?
C12 C8 C9 N1 178.34(18) . . . . ?
C7 C8 C9 C13 -179.19(19) . . . . ?
C12 C8 C9 C13 -0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 981162'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 6-ethyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          531.15
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   7.3809(6)
_cell_length_b                   8.0626(6)
_cell_length_c                   19.9265(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.378(6)
_cell_angle_gamma                90.00
_cell_volume                     1173.16(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          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5083
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         29.04
_reflns_number_total             2686
_reflns_number_gt                1537
_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)+(0.0729P)²+0.4762P] 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         2686
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1905
_refine_ls_wR_factor_gt          0.1581
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004

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
HN1 H -0.120(4) 0.920(3) 0.0251(15) 0.064(8) Uiso 1 1 d . . .
C7 C 0.0004(3) 0.8743(3) 0.20932(12) 0.0422(6) Uani 1 1 d . . .
C11 C 0.1280(3) 0.9366(3) 0.17143(12) 0.0430(6) Uani 1 1 d . . .
O1 O 0.1943(2) 1.0083(3) 0.06212(8) 0.0602(6) Uani 1 1 d . . .
N1 N -0.0848(3) 0.8997(3) 0.07137(11) 0.0506(6) Uani 1 1 d . . .
C12 C 0.3026(3) 0.9996(3) 0.20138(12) 0.0479(6) Uani 1 1 d . . .
C8 C -0.1721(3) 0.8247(3) 0.17535(13) 0.0512(7) Uani 1 1 d . . .
H8 H -0.2587 0.7816 0.2002 0.061 Uiso 1 1 calc R . .
C10 C 0.0874(3) 0.9518(3) 0.09914(12) 0.0473(6) Uani 1 1 d . . .
C6 C 0.0389(3) 0.8607(3) 0.28439(12) 0.0436(6) Uani 1 1 d . . .
C1 C 0.2001(4) 0.7908(3) 0.31661(13) 0.0524(7) Uani 1 1 d . . .
H1 H 0.2876 0.7528 0.2911 0.063 Uiso 1 1 calc R . .
C9 C -0.2137(4) 0.8390(4) 0.10700(13) 0.0533(7) Uani 1 1 d . . .
C5 C -0.0922(4) 0.9148(4) 0.32320(14) 0.0596(8) Uani 1 1 d . . .
H5 H -0.2020 0.9600 0.3022 0.072 Uiso 1 1 calc R . .
N2 N 0.4415(3) 1.0518(4) 0.22456(12) 0.0692(7) Uani 1 1 d . . .
C2 C 0.2308(5) 0.7775(4) 0.38617(15) 0.0688(9) Uani 1 1 d . . .
H2 H 0.3391 0.7305 0.4077 0.083 Uiso 1 1 calc R . .
C4 C -0.0584(5) 0.9011(4) 0.39244(15) 0.0751(10) Uani 1 1 d . . .
H4 H -0.1454 0.9382 0.4183 0.090 Uiso 1 1 calc R . .
C3 C 0.1014(5) 0.8336(5) 0.42394(15) 0.0788(10) Uani 1 1 d . . .
H3 H 0.1228 0.8255 0.4710 0.095 Uiso 1 1 calc R . .
C13 C -0.3943(4) 0.7935(5) 0.06578(16) 0.0824(11) Uani 1 1 d . . .
H13A H -0.4661 0.8941 0.0573 0.099 Uiso 1 1 calc R . .
H13B H -0.3702 0.7525 0.0222 0.099 Uiso 1 1 calc R . .
C14 C -0.5064(5) 0.6706(5) 0.0945(2) 0.0929(12) Uani 1 1 d . . .
H14A H -0.6138 0.6473 0.0626 0.139 Uiso 1 1 calc R . .
H14B H -0.5421 0.7133 0.1356 0.139 Uiso 1 1 calc R . .
H14C H -0.4371 0.5706 0.1042 0.139 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
C7 C11 1.384(3) . ?
C7 C8 1.410(3) . ?
C7 C6 1.486(3) . ?
C11 C10 1.433(3) . ?
C11 C12 1.433(3) . ?
O1 C10 1.243(3) . ?
N1 C9 1.359(3) . ?
N1 C10 1.376(3) . ?
N1 HN1 0.93(3) . ?
C12 N2 1.142(3) . ?
C8 C9 1.357(4) . ?
C8 H8 0.9300 . ?
C6 C1 1.386(3) . ?
C6 C5 1.394(4) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9300 . ?
C9 C13 1.506(4) . ?
C5 C4 1.370(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C4 C3 1.366(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C13 C14 1.460(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C11 C7 C8 118.7(2) . . ?
C11 C7 C6 122.0(2) . . ?
C8 C7 C6 119.3(2) . . ?
C7 C11 C10 121.3(2) . . ?
C7 C11 C12 123.0(2) . . ?
C10 C11 C12 115.6(2) . . ?
C9 N1 C10 125.2(2) . . ?
C9 N1 HN1 117.3(17) . . ?
C10 N1 HN1 117.1(17) . . ?
N2 C12 C11 179.0(3) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
O1 C10 N1 120.2(2) . . ?
O1 C10 C11 124.8(2) . . ?
N1 C10 C11 115.1(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 121.5(2) . . ?
C5 C6 C7 119.3(2) . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
N1 C9 C8 118.8(2) . . ?
N1 C9 C13 115.7(2) . . ?
C8 C9 C13 125.4(2) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C14 C13 C9 117.3(3) . . ?
C14 C13 H13A 108.0 . . ?
C9 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
C9 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C8 C7 C11 C10 0.3(4) . . . . ?
C6 C7 C11 C10 -178.8(2) . . . . ?
C8 C7 C11 C12 176.1(2) . . . . ?
C6 C7 C11 C12 -3.0(4) . . . . ?
C7 C11 C12 N2 -138(17) . . . . ?
C10 C11 C12 N2 38(17) . . . . ?
C11 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 C9 178.5(2) . . . . ?
C9 N1 C10 O1 -178.7(3) . . . . ?
C9 N1 C10 C11 0.8(4) . . . . ?
C7 C11 C10 O1 179.1(2) . . . . ?
C12 C11 C10 O1 3.1(4) . . . . ?
C7 C11 C10 N1 -0.3(4) . . . . ?
C12 C11 C10 N1 -176.4(2) . . . . ?
C11 C7 C6 C1 -48.1(3) . . . . ?
C8 C7 C6 C1 132.8(3) . . . . ?
C11 C7 C6 C5 133.8(3) . . . . ?
C8 C7 C6 C5 -45.2(3) . . . . ?
C5 C6 C1 C2 -1.0(4) . . . . ?
C7 C6 C1 C2 -179.0(2) . . . . ?
C10 N1 C9 C8 -1.2(4) . . . . ?
C10 N1 C9 C13 178.6(3) . . . . ?
C7 C8 C9 N1 1.0(4) . . . . ?
C7 C8 C9 C13 -178.6(3) . . . . ?
C1 C6 C5 C4 1.3(4) . . . . ?
C7 C6 C5 C4 179.3(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C5 C4 C3 -0.6(5) . . . . ?
C5 C4 C3 C2 -0.3(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
N1 C9 C13 C14 155.8(3) . . . . ?
C8 C9 C13 C14 -24.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 981163'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-(4-chlorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          543.15
_chemical_formula_moiety         'C14 H11 Cl N2 O'
_chemical_formula_sum            'C14 H11 Cl N2 O'
_chemical_formula_weight         258.70

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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                   9.3937(10)
_cell_length_b                   17.428(2)
_cell_length_c                   18.0482(18)
_cell_angle_alpha                61.217(12)
_cell_angle_beta                 78.071(9)
_cell_angle_gamma                87.092(9)
_cell_volume                     2529.7(5)
_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            ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21373
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         29.22
_reflns_number_total             11464
_reflns_number_gt                5232
_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)+(0.0882P)²+3.6686P] 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         11464
_refine_ls_number_parameters     665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1847
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2500
_refine_ls_wR_factor_gt          0.2144
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.021

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
HN3 H -0.012(4) 0.127(3) 0.990(3) 0.035(11) Uiso 1 1 d . . .
HN7 H 0.413(6) 0.324(4) -0.088(4) 0.077(19) Uiso 1 1 d . . .
HN1 H -0.279(6) 0.128(4) 1.054(4) 0.076(19) Uiso 1 1 d . . .
HN5 H 0.679(8) 0.322(5) 0.842(5) 0.13(3) Uiso 1 1 d . . .
Cl2 Cl 0.08131(18) 0.12236(10) 0.44911(9) 0.0703(4) Uani 1 1 d . . .
Cl1 Cl -0.4389(2) 0.12853(13) 1.59437(10) 0.0909(6) Uani 1 1 d . . .
N1 N -0.2909(4) 0.1345(3) 1.0998(3) 0.0467(10) Uani 1 1 d . . .
N3 N 0.0000(5) 0.1178(3) 0.9410(3) 0.0507(10) Uani 1 1 d . . .
C21 C 0.0403(5) 0.1071(3) 0.7915(3) 0.0419(11) Uani 1 1 d . . .
O1 O -0.0441(4) 0.1452(3) 1.0829(2) 0.0642(10) Uani 1 1 d . . .
C7 C -0.3381(5) 0.1398(3) 1.2504(3) 0.0420(11) Uani 1 1 d . . .
C11 C -0.1965(5) 0.1470(3) 1.2045(3) 0.0411(10) Uani 1 1 d . . .
C25 C -0.0984(5) 0.1131(3) 0.8326(3) 0.0439(11) Uani 1 1 d . . .
O2 O -0.2464(4) 0.1238(3) 0.9509(2) 0.0677(11) Uani 1 1 d . . .
C10 C -0.1688(5) 0.1425(3) 1.1260(3) 0.0452(11) Uani 1 1 d . . .
C8 C -0.4585(5) 0.1297(3) 1.2190(3) 0.0453(11) Uani 1 1 d . . .
C9 C -0.4299(5) 0.1283(3) 1.1425(3) 0.0442(11) Uani 1 1 d . . .
C6 C -0.3631(5) 0.1393(3) 1.3350(3) 0.0434(11) Uani 1 1 d . . .
C22 C 0.1606(5) 0.1047(3) 0.8277(3) 0.0456(11) Uani 1 1 d . . .
C26 C -0.2243(6) 0.1188(3) 0.7982(3) 0.0500(12) Uani 1 1 d . . .
C19 C 0.1471(5) 0.1697(3) 0.6340(3) 0.0496(12) Uani 1 1 d . . .
H19 H 0.2015 0.2105 0.6375 0.060 Uiso 1 1 calc R . .
C20 C 0.0574(5) 0.1061(3) 0.7085(3) 0.0403(10) Uani 1 1 d . . .
C24 C -0.1255(6) 0.1181(3) 0.9114(3) 0.0522(13) Uani 1 1 d . . .
C23 C 0.1370(5) 0.1111(3) 0.9027(3) 0.0493(12) Uani 1 1 d . . .
C3 C -0.4079(6) 0.1330(4) 1.4943(3) 0.0541(13) Uani 1 1 d . . .
C17 C 0.0734(5) 0.1152(3) 0.5495(3) 0.0461(11) Uani 1 1 d . . .
C12 C -0.0735(6) 0.1632(3) 1.2318(3) 0.0470(11) Uani 1 1 d . . .
C18 C 0.1571(5) 0.1735(3) 0.5554(3) 0.0543(13) Uani 1 1 d . . .
H18 H 0.2201 0.2151 0.5065 0.065 Uiso 1 1 calc R . .
N2 N 0.0251(5) 0.1774(3) 1.2507(3) 0.0658(13) Uani 1 1 d . . .
C14 C -0.5449(6) 0.1163(4) 1.1019(3) 0.0604(14) Uani 1 1 d . . .
H14A H -0.4997 0.1161 1.0492 0.091 Uiso 1 1 calc R . .
H14B H -0.6093 0.1635 1.0896 0.091 Uiso 1 1 calc R . .
H14C H -0.5993 0.0615 1.1410 0.091 Uiso 1 1 calc R . .
N4 N -0.3282(5) 0.1233(4) 0.7720(3) 0.0724(14) Uani 1 1 d . . .
C16 C -0.0139(6) 0.0501(3) 0.6223(3) 0.0531(13) Uani 1 1 d . . .
H16 H -0.0664 0.0090 0.6181 0.064 Uiso 1 1 calc R . .
C1 C -0.4269(6) 0.2065(4) 1.3464(3) 0.0596(14) Uani 1 1 d . . .
H1 H -0.4556 0.2543 1.3001 0.072 Uiso 1 1 calc R . .
C15 C -0.0229(6) 0.0462(3) 0.7012(3) 0.0519(13) Uani 1 1 d . . .
H15 H -0.0833 0.0030 0.7501 0.062 Uiso 1 1 calc R . .
C28 C 0.2550(6) 0.1124(4) 0.9469(4) 0.0629(15) Uani 1 1 d . . .
H28A H 0.2127 0.1179 0.9972 0.094 Uiso 1 1 calc R . .
H28B H 0.3231 0.1613 0.9080 0.094 Uiso 1 1 calc R . .
H28C H 0.3047 0.0589 0.9639 0.094 Uiso 1 1 calc R . .
C27 C 0.3137(6) 0.0938(4) 0.7887(4) 0.0646(15) Uani 1 1 d . . .
H27A H 0.3131 0.0909 0.7369 0.097 Uiso 1 1 calc R . .
H27B H 0.3491 0.0407 0.8293 0.097 Uiso 1 1 calc R . .
H27C H 0.3759 0.1429 0.7749 0.097 Uiso 1 1 calc R . .
C13 C -0.6158(6) 0.1190(4) 1.2674(3) 0.0655(15) Uani 1 1 d . . .
H13A H -0.6798 0.1134 1.2349 0.098 Uiso 1 1 calc R . .
H13B H -0.6388 0.1695 1.2750 0.098 Uiso 1 1 calc R . .
H13C H -0.6281 0.0674 1.3230 0.098 Uiso 1 1 calc R . .
C2 C -0.4492(6) 0.2044(4) 1.4259(4) 0.0637(15) Uani 1 1 d . . .
H2 H -0.4915 0.2506 1.4328 0.076 Uiso 1 1 calc R . .
C5 C -0.3199(6) 0.0693(4) 1.4044(3) 0.0602(14) Uani 1 1 d . . .
H5 H -0.2749 0.0237 1.3976 0.072 Uiso 1 1 calc R . .
C4 C -0.3432(6) 0.0666(4) 1.4841(3) 0.0667(16) Uani 1 1 d . . .
H4 H -0.3142 0.0191 1.5305 0.080 Uiso 1 1 calc R . .
Cl4 Cl 0.3159(2) 0.42271(12) 0.39988(11) 0.0918(6) Uani 1 1 d . . .
Cl3 Cl 0.8243(2) 0.40275(15) 0.26486(11) 0.1019(6) Uani 1 1 d . . .
O3 O 0.4442(4) 0.3212(3) 0.8053(3) 0.0719(11) Uani 1 1 d . . .
O4 O 0.6491(4) 0.3236(3) -0.0540(2) 0.0707(11) Uani 1 1 d . . .
N7 N 0.4053(5) 0.3395(3) -0.0464(3) 0.0548(11) Uani 1 1 d . . .
N5 N 0.6909(5) 0.3347(3) 0.7854(3) 0.0592(12) Uani 1 1 d . . .
C39 C 0.5923(5) 0.3419(3) 0.6730(3) 0.0465(11) Uani 1 1 d . . .
C40 C 0.4657(6) 0.3380(3) 0.6427(3) 0.0509(12) Uani 1 1 d . . .
C38 C 0.5673(6) 0.3312(3) 0.7580(3) 0.0526(13) Uani 1 1 d . . .
C35 C 0.7308(5) 0.3558(3) 0.6227(3) 0.0478(12) Uani 1 1 d . . .
C49 C 0.3793(5) 0.3751(3) 0.0874(3) 0.0458(11) Uani 1 1 d . . .
C53 C 0.5156(5) 0.3580(3) 0.0511(3) 0.0487(12) Uani 1 1 d . . .
C54 C 0.6446(6) 0.3569(3) 0.0813(3) 0.0536(13) Uani 1 1 d . . .
C37 C 0.8290(6) 0.3488(3) 0.7380(4) 0.0571(13) Uani 1 1 d . . .
C48 C 0.3643(5) 0.3893(3) 0.1638(3) 0.0466(12) Uani 1 1 d . . .
C36 C 0.8522(5) 0.3589(3) 0.6563(3) 0.0549(13) Uani 1 1 d . . .
C47 C 0.2545(6) 0.3433(3) 0.2359(3) 0.0559(13) Uani 1 1 d . . .
H47 H 0.1906 0.3042 0.2359 0.067 Uiso 1 1 calc R . .
N6 N 0.3649(5) 0.3350(3) 0.6183(4) 0.0750(14) Uani 1 1 d . . .
C46 C 0.2388(6) 0.3548(4) 0.3076(3) 0.0624(14) Uani 1 1 d . . .
H46 H 0.1649 0.3234 0.3556 0.075 Uiso 1 1 calc R . .
C52 C 0.5314(6) 0.3398(3) -0.0191(3) 0.0518(12) Uani 1 1 d . . .
C34 C 0.7517(5) 0.3672(3) 0.5346(3) 0.0496(12) Uani 1 1 d . . .
C33 C 0.7075(6) 0.4403(4) 0.4696(4) 0.0579(14) Uani 1 1 d . . .
H33 H 0.6612 0.4826 0.4818 0.070 Uiso 1 1 calc R . .
C50 C 0.2587(6) 0.3788(3) 0.0515(3) 0.0556(13) Uani 1 1 d . . .
C31 C 0.7938(6) 0.3891(4) 0.3690(4) 0.0644(15) Uani 1 1 d . . .
N8 N 0.7500(6) 0.3571(4) 0.1033(4) 0.0808(15) Uani 1 1 d . . .
C45 C 0.3322(6) 0.4124(3) 0.3080(3) 0.0570(13) Uani 1 1 d . . .
C43 C 0.4572(6) 0.4475(3) 0.1652(3) 0.0572(13) Uani 1 1 d . . .
H43 H 0.5308 0.4792 0.1171 0.069 Uiso 1 1 calc R . .
C30 C 0.8393(7) 0.3148(4) 0.4330(4) 0.0718(16) Uani 1 1 d . . .
H30 H 0.8843 0.2724 0.4205 0.086 Uiso 1 1 calc R . .
C29 C 0.8178(6) 0.3037(4) 0.5151(4) 0.0628(15) Uani 1 1 d . . .
H29 H 0.8476 0.2533 0.5583 0.075 Uiso 1 1 calc R . .
C44 C 0.4422(6) 0.4591(3) 0.2371(4) 0.0620(14) Uani 1 1 d . . .
H44 H 0.5057 0.4980 0.2376 0.074 Uiso 1 1 calc R . .
C51 C 0.2737(6) 0.3587(3) -0.0145(3) 0.0565(13) Uani 1 1 d . . .
C56 C 0.1502(7) 0.3566(5) -0.0563(4) 0.0792(18) Uani 1 1 d . . .
H56A H 0.1869 0.3420 -0.1014 0.119 Uiso 1 1 calc R . .
H56B H 0.1100 0.4132 -0.0804 0.119 Uiso 1 1 calc R . .
H56C H 0.0757 0.3135 -0.0136 0.119 Uiso 1 1 calc R . .
C42 C 0.9455(7) 0.3549(5) 0.7813(4) 0.089(2) Uani 1 1 d . . .
H42A H 0.9017 0.3467 0.8378 0.133 Uiso 1 1 calc R . .
H42B H 0.9960 0.4116 0.7473 0.133 Uiso 1 1 calc R . .
H42C H 1.0133 0.3104 0.7863 0.133 Uiso 1 1 calc R . .
C32 C 0.7305(6) 0.4527(4) 0.3857(4) 0.0658(15) Uani 1 1 d . . .
H32 H 0.7031 0.5036 0.3419 0.079 Uiso 1 1 calc R . .
C41 C 1.0038(7) 0.3832(5) 0.6007(5) 0.089(2) Uani 1 1 d . . .
H41A H 1.0026 0.3863 0.5463 0.133 Uiso 1 1 calc R . .
H41B H 1.0687 0.3397 0.6294 0.133 Uiso 1 1 calc R . .
H41C H 1.0366 0.4392 0.5909 0.133 Uiso 1 1 calc R . .
C55 C 0.1148(7) 0.4105(5) 0.0782(5) 0.102(2) Uani 1 1 d . . .
H55A H 0.0454 0.4054 0.0483 0.153 Uiso 1 1 calc R . .
H55B H 0.1276 0.4707 0.0638 0.153 Uiso 1 1 calc R . .
H55C H 0.0799 0.3756 0.1394 0.153 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
Cl2 C17 1.742(5) . ?
Cl1 C3 1.732(5) . ?
N1 C10 1.364(6) . ?
N1 C9 1.352(6) . ?
N1 HN1 0.86(6) . ?
N3 C23 1.357(6) . ?
N3 C24 1.391(6) . ?
N3 HN3 0.95(4) . ?
C21 C25 1.385(6) . ?
C21 C22 1.408(6) . ?
C21 C20 1.482(6) . ?
O1 C10 1.254(5) . ?
C7 C11 1.391(6) . ?
C7 C8 1.419(6) . ?
C7 C6 1.490(6) . ?
C11 C10 1.427(6) . ?
C11 C12 1.435(7) . ?
C25 C26 1.423(7) . ?
C25 C24 1.437(6) . ?
O2 C24 1.237(6) . ?
C8 C9 1.364(6) . ?
C8 C13 1.523(7) . ?
C9 C14 1.498(6) . ?
C6 C1 1.372(7) . ?
C6 C5 1.382(6) . ?
C22 C23 1.382(6) . ?
C22 C27 1.511(7) . ?
C26 N4 1.153(6) . ?
C19 C18 1.372(6) . ?
C19 C20 1.392(6) . ?
C19 H19 0.9300 . ?
C20 C15 1.389(6) . ?
C23 C28 1.501(7) . ?
C3 C4 1.354(7) . ?
C3 C2 1.375(7) . ?
C17 C18 1.370(7) . ?
C17 C16 1.378(7) . ?
C12 N2 1.127(6) . ?
C18 H18 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C15 1.378(6) . ?
C16 H16 0.9300 . ?
C1 C2 1.390(7) . ?
C1 H1 0.9300 . ?
C15 H15 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 H2 0.9300 . ?
C5 C4 1.388(7) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
Cl4 C45 1.728(5) . ?
Cl3 C31 1.739(6) . ?
O3 C38 1.251(6) . ?
O4 C52 1.246(6) . ?
N7 C51 1.349(7) . ?
N7 C52 1.375(6) . ?
N7 HN7 0.91(6) . ?
N5 C37 1.359(7) . ?
N5 C38 1.367(6) . ?
N5 HN5 0.92(7) . ?
C39 C35 1.382(7) . ?
C39 C40 1.425(7) . ?
C39 C38 1.423(7) . ?
C40 N6 1.137(6) . ?
C35 C36 1.413(7) . ?
C35 C34 1.476(7) . ?
C49 C53 1.400(7) . ?
C49 C50 1.401(7) . ?
C49 C48 1.493(7) . ?
C53 C52 1.425(7) . ?
C53 C54 1.424(7) . ?
C54 N8 1.140(6) . ?
C37 C36 1.370(7) . ?
C37 C42 1.504(7) . ?
C48 C43 1.384(7) . ?
C48 C47 1.387(7) . ?
C36 C41 1.509(8) . ?
C47 C46 1.380(7) . ?
C47 H47 0.9300 . ?
C46 C45 1.370(7) . ?
C46 H46 0.9300 . ?
C34 C33 1.371(7) . ?
C34 C29 1.395(7) . ?
C33 C32 1.393(7) . ?
C33 H33 0.9300 . ?
C50 C51 1.375(7) . ?
C50 C55 1.508(8) . ?
C31 C32 1.362(8) . ?
C31 C30 1.379(8) . ?
C45 C44 1.380(7) . ?
C43 C44 1.386(7) . ?
C43 H43 0.9300 . ?
C30 C29 1.370(7) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C44 H44 0.9300 . ?
C51 C56 1.520(7) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C32 H32 0.9300 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 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
C10 N1 C9 126.0(4) . . ?
C10 N1 HN1 117(4) . . ?
C9 N1 HN1 117(4) . . ?
C23 N3 C24 125.1(4) . . ?
C23 N3 HN3 118(3) . . ?
C24 N3 HN3 117(3) . . ?
C25 C21 C22 119.8(4) . . ?
C25 C21 C20 118.3(4) . . ?
C22 C21 C20 121.9(4) . . ?
C11 C7 C8 120.5(4) . . ?
C11 C7 C6 119.6(4) . . ?
C8 C7 C6 119.8(4) . . ?
C7 C11 C10 120.9(4) . . ?
C7 C11 C12 121.6(4) . . ?
C10 C11 C12 117.4(4) . . ?
C21 C25 C26 122.9(4) . . ?
C21 C25 C24 122.4(4) . . ?
C26 C25 C24 114.6(4) . . ?
O1 C10 N1 121.1(4) . . ?
O1 C10 C11 124.4(4) . . ?
N1 C10 C11 114.5(4) . . ?
C9 C8 C7 117.7(4) . . ?
C9 C8 C13 119.3(4) . . ?
C7 C8 C13 123.0(4) . . ?
N1 C9 C8 120.4(4) . . ?
N1 C9 C14 115.6(4) . . ?
C8 C9 C14 123.9(4) . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 C7 122.3(4) . . ?
C5 C6 C7 119.2(4) . . ?
C23 C22 C21 118.5(4) . . ?
C23 C22 C27 119.0(4) . . ?
C21 C22 C27 122.5(4) . . ?
N4 C26 C25 178.5(5) . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 118.1(4) . . ?
C15 C20 C21 121.3(4) . . ?
C19 C20 C21 120.5(4) . . ?
O2 C24 N3 120.8(4) . . ?
O2 C24 C25 125.5(5) . . ?
N3 C24 C25 113.7(4) . . ?
N3 C23 C22 120.3(4) . . ?
N3 C23 C28 115.2(4) . . ?
C22 C23 C28 124.4(5) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 Cl1 119.8(4) . . ?
C2 C3 Cl1 119.5(4) . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 Cl2 119.3(4) . . ?
C16 C17 Cl2 119.8(4) . . ?
N2 C12 C11 178.0(6) . . ?
C19 C18 C17 119.3(5) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C16 C17 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C6 C1 C2 121.2(5) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C16 C15 C20 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C20 C15 H15 119.7 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C51 N7 C52 125.0(5) . . ?
C51 N7 HN7 119(4) . . ?
C52 N7 HN7 116(4) . . ?
C37 N5 C38 125.5(5) . . ?
C37 N5 HN5 118(5) . . ?
C38 N5 HN5 116(5) . . ?
C35 C39 C40 122.0(5) . . ?
C35 C39 C38 122.0(4) . . ?
C40 C39 C38 116.0(4) . . ?
N6 C40 C39 179.8(6) . . ?
O3 C38 N5 120.8(5) . . ?
O3 C38 C39 124.7(5) . . ?
N5 C38 C39 114.5(5) . . ?
C39 C35 C36 119.4(5) . . ?
C39 C35 C34 120.3(4) . . ?
C36 C35 C34 120.3(5) . . ?
C53 C49 C50 119.7(5) . . ?
C53 C49 C48 119.6(4) . . ?
C50 C49 C48 120.8(5) . . ?
C49 C53 C52 120.7(4) . . ?
C49 C53 C54 123.1(5) . . ?
C52 C53 C54 116.2(5) . . ?
N8 C54 C53 178.2(6) . . ?
C36 C37 N5 119.6(5) . . ?
C36 C37 C42 125.3(5) . . ?
N5 C37 C42 115.0(5) . . ?
C43 C48 C47 118.5(5) . . ?
C43 C48 C49 121.8(4) . . ?
C47 C48 C49 119.7(4) . . ?
C37 C36 C35 118.9(5) . . ?
C37 C36 C41 119.5(5) . . ?
C35 C36 C41 121.3(5) . . ?
C46 C47 C48 120.8(5) . . ?
C46 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
C45 C46 C47 119.9(5) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
O4 C52 N7 120.5(5) . . ?
O4 C52 C53 124.0(5) . . ?
N7 C52 C53 115.5(5) . . ?
C33 C34 C29 118.2(5) . . ?
C33 C34 C35 121.1(5) . . ?
C29 C34 C35 120.7(5) . . ?
C34 C33 C32 121.4(5) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C51 C50 C49 119.2(5) . . ?
C51 C50 C55 118.2(5) . . ?
C49 C50 C55 122.4(5) . . ?
C32 C31 C30 120.9(5) . . ?
C32 C31 Cl3 120.0(5) . . ?
C30 C31 Cl3 119.1(5) . . ?
C46 C45 C44 120.4(5) . . ?
C46 C45 Cl4 119.4(4) . . ?
C44 C45 Cl4 120.1(4) . . ?
C48 C43 C44 120.9(5) . . ?
C48 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C29 C30 C31 119.7(5) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.1 . . ?
C30 C29 C34 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
C34 C29 H29 119.6 . . ?
C43 C44 C45 119.4(5) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
N7 C51 C50 119.8(5) . . ?
N7 C51 C56 115.9(5) . . ?
C50 C51 C56 124.4(5) . . ?
C51 C56 H56A 109.5 . . ?
C51 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C51 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C31 C32 C33 119.0(5) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C50 C55 H55A 109.5 . . ?
C50 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C50 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 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
C8 C7 C11 C10 -1.3(7) . . . . ?
C6 C7 C11 C10 176.3(4) . . . . ?
C8 C7 C11 C12 175.6(4) . . . . ?
C6 C7 C11 C12 -6.7(7) . . . . ?
C22 C21 C25 C26 177.8(4) . . . . ?
C20 C21 C25 C26 -0.4(7) . . . . ?
C22 C21 C25 C24 0.8(7) . . . . ?
C20 C21 C25 C24 -177.3(4) . . . . ?
C9 N1 C10 O1 177.9(5) . . . . ?
C9 N1 C10 C11 -1.9(7) . . . . ?
C7 C11 C10 O1 -177.3(5) . . . . ?
C12 C11 C10 O1 5.6(7) . . . . ?
C7 C11 C10 N1 2.5(6) . . . . ?
C12 C11 C10 N1 -174.6(4) . . . . ?
C11 C7 C8 C9 -0.6(7) . . . . ?
C6 C7 C8 C9 -178.3(4) . . . . ?
C11 C7 C8 C13 178.2(5) . . . . ?
C6 C7 C8 C13 0.6(7) . . . . ?
C10 N1 C9 C8 0.0(7) . . . . ?
C10 N1 C9 C14 -177.5(4) . . . . ?
C7 C8 C9 N1 1.3(7) . . . . ?
C13 C8 C9 N1 -177.6(5) . . . . ?
C7 C8 C9 C14 178.7(4) . . . . ?
C13 C8 C9 C14 -0.2(7) . . . . ?
C11 C7 C6 C1 112.6(5) . . . . ?
C8 C7 C6 C1 -69.8(6) . . . . ?
C11 C7 C6 C5 -66.9(6) . . . . ?
C8 C7 C6 C5 110.7(5) . . . . ?
C25 C21 C22 C23 -1.8(7) . . . . ?
C20 C21 C22 C23 176.2(4) . . . . ?
C25 C21 C22 C27 176.9(5) . . . . ?
C20 C21 C22 C27 -5.0(7) . . . . ?
C21 C25 C26 N4 175(100) . . . . ?
C24 C25 C26 N4 -8(24) . . . . ?
C18 C19 C20 C15 -0.2(7) . . . . ?
C18 C19 C20 C21 -175.7(4) . . . . ?
C25 C21 C20 C15 -53.8(6) . . . . ?
C22 C21 C20 C15 128.1(5) . . . . ?
C25 C21 C20 C19 121.5(5) . . . . ?
C22 C21 C20 C19 -56.5(6) . . . . ?
C23 N3 C24 O2 179.3(5) . . . . ?
C23 N3 C24 C25 -1.7(7) . . . . ?
C21 C25 C24 O2 179.8(5) . . . . ?
C26 C25 C24 O2 2.6(8) . . . . ?
C21 C25 C24 N3 0.9(7) . . . . ?
C26 C25 C24 N3 -176.3(4) . . . . ?
C24 N3 C23 C22 0.7(8) . . . . ?
C24 N3 C23 C28 179.8(5) . . . . ?
C21 C22 C23 N3 1.1(7) . . . . ?
C27 C22 C23 N3 -177.7(5) . . . . ?
C21 C22 C23 C28 -177.9(5) . . . . ?
C27 C22 C23 C28 3.3(7) . . . . ?
C7 C11 C12 N2 -146(15) . . . . ?
C10 C11 C12 N2 31(16) . . . . ?
C20 C19 C18 C17 2.2(8) . . . . ?
C16 C17 C18 C19 -3.8(8) . . . . ?
Cl2 C17 C18 C19 177.8(4) . . . . ?
C18 C17 C16 C15 3.4(8) . . . . ?
Cl2 C17 C16 C15 -178.2(4) . . . . ?
C5 C6 C1 C2 -0.6(8) . . . . ?
C7 C6 C1 C2 179.9(5) . . . . ?
C17 C16 C15 C20 -1.3(8) . . . . ?
C19 C20 C15 C16 -0.2(7) . . . . ?
C21 C20 C15 C16 175.2(4) . . . . ?
C4 C3 C2 C1 1.6(9) . . . . ?
Cl1 C3 C2 C1 -178.6(4) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?
C1 C6 C5 C4 1.2(8) . . . . ?
C7 C6 C5 C4 -179.3(5) . . . . ?
C2 C3 C4 C5 -1.1(9) . . . . ?
Cl1 C3 C4 C5 179.1(4) . . . . ?
C6 C5 C4 C3 -0.3(9) . . . . ?
C35 C39 C40 N6 -4(100) . . . . ?
C38 C39 C40 N6 176(100) . . . . ?
C37 N5 C38 O3 -177.2(5) . . . . ?
C37 N5 C38 C39 1.3(8) . . . . ?
C35 C39 C38 O3 177.7(5) . . . . ?
C40 C39 C38 O3 -2.0(7) . . . . ?
C35 C39 C38 N5 -0.7(7) . . . . ?
C40 C39 C38 N5 179.6(4) . . . . ?
C40 C39 C35 C36 -179.9(4) . . . . ?
C38 C39 C35 C36 0.4(7) . . . . ?
C40 C39 C35 C34 0.1(7) . . . . ?
C38 C39 C35 C34 -179.6(4) . . . . ?
C50 C49 C53 C52 -3.3(7) . . . . ?
C48 C49 C53 C52 176.8(4) . . . . ?
C50 C49 C53 C54 177.2(5) . . . . ?
C48 C49 C53 C54 -2.8(7) . . . . ?
C49 C53 C54 N8 -143(18) . . . . ?
C52 C53 C54 N8 37(19) . . . . ?
C38 N5 C37 C36 -1.5(8) . . . . ?
C38 N5 C37 C42 176.6(5) . . . . ?
C53 C49 C48 C43 49.9(6) . . . . ?
C50 C49 C48 C43 -130.0(5) . . . . ?
C53 C49 C48 C47 -130.1(5) . . . . ?
C50 C49 C48 C47 49.9(6) . . . . ?
N5 C37 C36 C35 1.0(8) . . . . ?
C42 C37 C36 C35 -176.8(5) . . . . ?
N5 C37 C36 C41 174.1(5) . . . . ?
C42 C37 C36 C41 -3.7(9) . . . . ?
C39 C35 C36 C37 -0.5(7) . . . . ?
C34 C35 C36 C37 179.5(5) . . . . ?
C39 C35 C36 C41 -173.5(5) . . . . ?
C34 C35 C36 C41 6.5(8) . . . . ?
C43 C48 C47 C46 -0.5(8) . . . . ?
C49 C48 C47 C46 179.6(5) . . . . ?
C48 C47 C46 C45 0.2(8) . . . . ?
C51 N7 C52 O4 -178.0(5) . . . . ?
C51 N7 C52 C53 3.1(7) . . . . ?
C49 C53 C52 O4 -179.6(5) . . . . ?
C54 C53 C52 O4 0.0(7) . . . . ?
C49 C53 C52 N7 -0.7(7) . . . . ?
C54 C53 C52 N7 178.9(4) . . . . ?
C39 C35 C34 C33 68.5(6) . . . . ?
C36 C35 C34 C33 -111.5(6) . . . . ?
C39 C35 C34 C29 -111.8(6) . . . . ?
C36 C35 C34 C29 68.2(6) . . . . ?
C29 C34 C33 C32 -1.5(8) . . . . ?
C35 C34 C33 C32 178.2(5) . . . . ?
C53 C49 C50 C51 5.1(7) . . . . ?
C48 C49 C50 C51 -174.9(4) . . . . ?
C53 C49 C50 C55 -170.3(5) . . . . ?
C48 C49 C50 C55 9.6(8) . . . . ?
C47 C46 C45 C44 0.0(8) . . . . ?
C47 C46 C45 Cl4 -177.3(4) . . . . ?
C47 C48 C43 C44 0.6(8) . . . . ?
C49 C48 C43 C44 -179.4(5) . . . . ?
C32 C31 C30 C29 1.4(9) . . . . ?
Cl3 C31 C30 C29 179.1(5) . . . . ?
C31 C30 C29 C34 -0.7(9) . . . . ?
C33 C34 C29 C30 0.7(8) . . . . ?
C35 C34 C29 C30 -179.0(5) . . . . ?
C48 C43 C44 C45 -0.5(8) . . . . ?
C46 C45 C44 C43 0.2(8) . . . . ?
Cl4 C45 C44 C43 177.5(4) . . . . ?
C52 N7 C51 C50 -1.3(8) . . . . ?
C52 N7 C51 C56 178.4(5) . . . . ?
C49 C50 C51 N7 -3.0(7) . . . . ?
C55 C50 C51 N7 172.7(5) . . . . ?
C49 C50 C51 C56 177.4(5) . . . . ?
C55 C50 C51 C56 -6.9(8) . . . . ?
C30 C31 C32 C33 -2.2(9) . . . . ?
Cl3 C31 C32 C33 -179.9(4) . . . . ?
C34 C33 C32 C31 2.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 25.24
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 25.24
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 981164'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-oxo-4-phenyl-6-propyl-1,2-dihydropyridine-3-carbonitrile 
;
_chemical_name_common            ?
_chemical_melting_point          468.15
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28

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                   9.7064(10)
_cell_length_b                   9.7294(10)
_cell_length_c                   14.4315(14)
_cell_angle_alpha                82.404(8)
_cell_angle_beta                 77.082(9)
_cell_angle_gamma                75.690(9)
_cell_volume                     1282.9(2)
_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          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.48
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96616
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10237
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         29.12
_reflns_number_total             5798
_reflns_number_gt                3291
_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)+(0.0546P)²+0.1504P] 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         5798
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
HN2 H -0.046(2) 0.344(2) 0.4454(16) 0.064(7) Uiso 1 1 d . . .
HN1 H 0.049(2) 0.155(2) 0.5579(17) 0.076(7) Uiso 1 1 d . . .
C16 C 0.1035(2) 0.27749(19) 0.02764(13) 0.0405(5) Uani 1 1 d . . .
H16 H 0.0033 0.3040 0.0472 0.049 Uiso 1 1 calc R . .
C1 C -0.2129(2) 0.1250(2) 0.97823(13) 0.0419(5) Uani 1 1 d . . .
H1 H -0.1808 0.0336 0.9579 0.050 Uiso 1 1 calc R . .
C20 C 0.3418(2) 0.2164(2) 0.06294(13) 0.0442(5) Uani 1 1 d . . .
H20 H 0.4028 0.2015 0.1064 0.053 Uiso 1 1 calc R . .
C5 C -0.2485(2) 0.3769(2) 0.94577(13) 0.0423(5) Uani 1 1 d . . .
H5 H -0.2403 0.4566 0.9034 0.051 Uiso 1 1 calc R . .
C17 C 0.1635(2) 0.2613(2) -0.06748(13) 0.0455(5) Uani 1 1 d . . .
H17 H 0.1033 0.2764 -0.1115 0.055 Uiso 1 1 calc R . .
C19 C 0.4002(2) 0.2006(2) -0.03264(14) 0.0500(5) Uani 1 1 d . . .
H19 H 0.5003 0.1747 -0.0529 0.060 Uiso 1 1 calc R . .
C2 C -0.2729(2) 0.1431(2) 1.07336(13) 0.0474(5) Uani 1 1 d . . .
H2 H -0.2810 0.0641 1.1164 0.057 Uiso 1 1 calc R . .
N3 N -0.00060(18) 0.32740(17) 0.38241(11) 0.0434(4) Uani 1 1 d . . .
N1 N 0.00053(18) 0.16821(17) 0.62482(11) 0.0432(4) Uani 1 1 d . . .
C4 C -0.3087(2) 0.3940(2) 1.04088(14) 0.0475(5) Uani 1 1 d . . .
H4 H -0.3414 0.4849 1.0619 0.057 Uiso 1 1 calc R . .
C22 C 0.12667(19) 0.27522(19) 0.19659(12) 0.0350(4) Uani 1 1 d . . .
O2 O 0.14167(17) 0.12425(16) 0.43822(9) 0.0618(5) Uani 1 1 d . . .
C23 C 0.1733(2) 0.18248(19) 0.27060(12) 0.0374(4) Uani 1 1 d . . .
C11 C -0.0196(2) 0.09937(19) 0.78857(12) 0.0380(5) Uani 1 1 d . . .
H11 H 0.0117 0.0362 0.8379 0.046 Uiso 1 1 calc R . .
C7 C -0.13384(19) 0.21975(19) 0.81037(12) 0.0335(4) Uani 1 1 d . . .
C8 C -0.1775(2) 0.3126(2) 0.73549(12) 0.0380(5) Uani 1 1 d . . .
C26 C 0.0126(2) 0.3945(2) 0.21902(13) 0.0390(5) Uani 1 1 d . . .
H26 H -0.0213 0.4564 0.1700 0.047 Uiso 1 1 calc R . .
O1 O -0.13974(17) 0.37147(16) 0.56807(9) 0.0640(5) Uani 1 1 d . . .
C27 C 0.2854(2) 0.0544(2) 0.25595(13) 0.0439(5) Uani 1 1 d . . .
C24 C 0.1083(2) 0.2058(2) 0.36884(13) 0.0430(5) Uani 1 1 d . . .
C6 C -0.19986(19) 0.24150(19) 0.91245(12) 0.0344(4) Uani 1 1 d . . .
C25 C -0.0490(2) 0.42061(19) 0.31161(13) 0.0389(5) Uani 1 1 d . . .
C10 C 0.0455(2) 0.0744(2) 0.69635(13) 0.0377(5) Uani 1 1 d . . .
C9 C -0.1082(2) 0.2892(2) 0.63769(13) 0.0437(5) Uani 1 1 d . . .
C13 C 0.1710(2) -0.0466(2) 0.66691(13) 0.0426(5) Uani 1 1 d . . .
H13A H 0.1570 -0.0843 0.6116 0.051 Uiso 1 1 calc R . .
H13B H 0.1734 -0.1220 0.7182 0.051 Uiso 1 1 calc R . .
C21 C 0.19191(19) 0.25448(18) 0.09437(12) 0.0341(4) Uani 1 1 d . . .
C28 C -0.1725(2) 0.5423(2) 0.34237(14) 0.0460(5) Uani 1 1 d . . .
H28A H -0.1698 0.6212 0.2937 0.055 Uiso 1 1 calc R . .
H28B H -0.1605 0.5734 0.4007 0.055 Uiso 1 1 calc R . .
C12 C -0.2955(2) 0.4354(2) 0.74655(13) 0.0502(6) Uani 1 1 d . . .
N4 N 0.3736(2) -0.0476(2) 0.24497(13) 0.0646(6) Uani 1 1 d . . .
C3 C -0.3206(2) 0.2776(2) 1.10470(13) 0.0473(5) Uani 1 1 d . . .
H3 H -0.3606 0.2896 1.1688 0.057 Uiso 1 1 calc R . .
N2 N -0.3885(2) 0.5338(2) 0.75239(14) 0.0815(7) Uani 1 1 d . . .
C14 C 0.3153(2) -0.0027(2) 0.64313(15) 0.0515(6) Uani 1 1 d . . .
H14A H 0.3106 0.0767 0.5947 0.062 Uiso 1 1 calc R . .
H14B H 0.3319 0.0295 0.6997 0.062 Uiso 1 1 calc R . .
C18 C 0.3120(2) 0.2227(2) -0.09786(14) 0.0475(5) Uani 1 1 d . . .
H18 H 0.3519 0.2119 -0.1621 0.057 Uiso 1 1 calc R . .
C15 C 0.4419(2) -0.1221(3) 0.60746(17) 0.0721(7) Uani 1 1 d . . .
H15A H 0.5301 -0.0888 0.5937 0.108 Uiso 1 1 calc R . .
H15B H 0.4274 -0.1529 0.5505 0.108 Uiso 1 1 calc R . .
H15C H 0.4483 -0.2005 0.6555 0.108 Uiso 1 1 calc R . .
C30 C -0.4426(3) 0.6256(3) 0.39568(18) 0.0761(8) Uani 1 1 d . . .
H30A H -0.5324 0.5963 0.4048 0.114 Uiso 1 1 calc R . .
H30B H -0.4435 0.7069 0.3501 0.114 Uiso 1 1 calc R . .
H30C H -0.4307 0.6499 0.4553 0.114 Uiso 1 1 calc R . .
C29 C -0.3180(2) 0.5051(2) 0.35928(17) 0.0622(7) Uani 1 1 d . . .
H29A H -0.3187 0.4228 0.4052 0.075 Uiso 1 1 calc R . .
H29B H -0.3323 0.4792 0.3000 0.075 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
C16 C17 1.379(2) . ?
C16 C21 1.390(3) . ?
C16 H16 0.9300 . ?
C1 C2 1.382(2) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9300 . ?
C20 C19 1.382(3) . ?
C20 C21 1.394(2) . ?
C20 H20 0.9300 . ?
C5 C4 1.381(2) . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C19 C18 1.371(3) . ?
C19 H19 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
N3 C25 1.359(2) . ?
N3 C24 1.380(2) . ?
N3 HN2 0.93(2) . ?
N1 C10 1.358(2) . ?
N1 C9 1.375(2) . ?
N1 HN1 0.98(2) . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C22 C23 1.385(3) . ?
C22 C26 1.407(2) . ?
C22 C21 1.489(2) . ?
O2 C24 1.243(2) . ?
C23 C24 1.440(2) . ?
C23 C27 1.442(3) . ?
C11 C10 1.365(2) . ?
C11 C7 1.414(2) . ?
C11 H11 0.9300 . ?
C7 C8 1.386(3) . ?
C7 C6 1.490(2) . ?
C8 C12 1.434(3) . ?
C8 C9 1.443(2) . ?
C26 C25 1.366(2) . ?
C26 H26 0.9300 . ?
O1 C9 1.244(2) . ?
C27 N4 1.141(2) . ?
C25 C28 1.495(2) . ?
C10 C13 1.498(2) . ?
C13 C14 1.519(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C28 C29 1.504(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C12 N2 1.140(3) . ?
C3 H3 0.9300 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C18 H18 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C30 C29 1.513(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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
C17 C16 C21 120.38(18) . . ?
C17 C16 H16 119.8 . . ?
C21 C16 H16 119.8 . . ?
C2 C1 C6 120.94(18) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C19 C20 C21 120.24(19) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C4 C5 C6 120.80(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C18 C19 C20 120.69(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C3 C2 C1 120.29(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C25 N3 C24 125.13(16) . . ?
C25 N3 HN2 118.1(14) . . ?
C24 N3 HN2 116.8(14) . . ?
C10 N1 C9 124.79(16) . . ?
C10 N1 HN1 120.8(14) . . ?
C9 N1 HN1 114.4(14) . . ?
C3 C4 C5 120.47(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C23 C22 C26 118.56(16) . . ?
C23 C22 C21 122.94(16) . . ?
C26 C22 C21 118.51(17) . . ?
C22 C23 C24 121.60(17) . . ?
C22 C23 C27 123.32(16) . . ?
C24 C23 C27 115.05(18) . . ?
C10 C11 C7 121.06(18) . . ?
C10 C11 H11 119.5 . . ?
C7 C11 H11 119.5 . . ?
C8 C7 C11 118.20(15) . . ?
C8 C7 C6 123.30(16) . . ?
C11 C7 C6 118.49(17) . . ?
C7 C8 C12 124.35(16) . . ?
C7 C8 C9 121.46(17) . . ?
C12 C8 C9 114.17(18) . . ?
C25 C26 C22 121.01(18) . . ?
C25 C26 H26 119.5 . . ?
C22 C26 H26 119.5 . . ?
N4 C27 C23 179.5(2) . . ?
O2 C24 N3 120.45(17) . . ?
O2 C24 C23 124.70(18) . . ?
N3 C24 C23 114.82(18) . . ?
C1 C6 C5 117.84(16) . . ?
C1 C6 C7 120.15(16) . . ?
C5 C6 C7 122.01(17) . . ?
N3 C25 C26 118.85(17) . . ?
N3 C25 C28 116.22(16) . . ?
C26 C25 C28 124.87(19) . . ?
N1 C10 C11 119.12(17) . . ?
N1 C10 C13 116.14(15) . . ?
C11 C10 C13 124.65(18) . . ?
O1 C9 N1 120.51(17) . . ?
O1 C9 C8 124.11(18) . . ?
N1 C9 C8 115.36(18) . . ?
C10 C13 C14 112.56(16) . . ?
C10 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C10 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C16 C21 C20 118.63(16) . . ?
C16 C21 C22 120.13(16) . . ?
C20 C21 C22 121.21(17) . . ?
C25 C28 C29 112.97(17) . . ?
C25 C28 H28A 109.0 . . ?
C29 C28 H28A 109.0 . . ?
C25 C28 H28B 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
N2 C12 C8 177.9(2) . . ?
C4 C3 C2 119.65(17) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C15 C14 C13 112.92(18) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C19 C18 C17 119.47(18) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
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 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C29 C30 113.04(19) . . ?
C28 C29 H29A 109.0 . . ?
C30 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
C30 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?

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
C21 C16 C17 C18 -0.3(3) . . . . ?
C21 C20 C19 C18 0.3(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C26 C22 C23 C24 -0.2(3) . . . . ?
C21 C22 C23 C24 179.74(17) . . . . ?
C26 C22 C23 C27 177.65(18) . . . . ?
C21 C22 C23 C27 -2.4(3) . . . . ?
C10 C11 C7 C8 -0.4(3) . . . . ?
C10 C11 C7 C6 -179.68(17) . . . . ?
C11 C7 C8 C12 177.28(19) . . . . ?
C6 C7 C8 C12 -3.5(3) . . . . ?
C11 C7 C8 C9 -0.7(3) . . . . ?
C6 C7 C8 C9 178.51(17) . . . . ?
C23 C22 C26 C25 1.5(3) . . . . ?
C21 C22 C26 C25 -178.44(17) . . . . ?
C22 C23 C27 N4 -143(29) . . . . ?
C24 C23 C27 N4 35(29) . . . . ?
C25 N3 C24 O2 -177.5(2) . . . . ?
C25 N3 C24 C23 1.0(3) . . . . ?
C22 C23 C24 O2 177.4(2) . . . . ?
C27 C23 C24 O2 -0.6(3) . . . . ?
C22 C23 C24 N3 -1.0(3) . . . . ?
C27 C23 C24 N3 -178.99(17) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 179.51(19) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.70(18) . . . . ?
C8 C7 C6 C1 146.21(19) . . . . ?
C11 C7 C6 C1 -34.6(3) . . . . ?
C8 C7 C6 C5 -34.7(3) . . . . ?
C11 C7 C6 C5 144.52(19) . . . . ?
C24 N3 C25 C26 0.2(3) . . . . ?
C24 N3 C25 C28 177.52(18) . . . . ?
C22 C26 C25 N3 -1.5(3) . . . . ?
C22 C26 C25 C28 -178.55(18) . . . . ?
C9 N1 C10 C11 -0.3(3) . . . . ?
C9 N1 C10 C13 -176.95(18) . . . . ?
C7 C11 C10 N1 0.9(3) . . . . ?
C7 C11 C10 C13 177.29(17) . . . . ?
C10 N1 C9 O1 178.0(2) . . . . ?
C10 N1 C9 C8 -0.8(3) . . . . ?
C7 C8 C9 O1 -177.5(2) . . . . ?
C12 C8 C9 O1 4.4(3) . . . . ?
C7 C8 C9 N1 1.3(3) . . . . ?
C12 C8 C9 N1 -176.91(18) . . . . ?
N1 C10 C13 C14 77.7(2) . . . . ?
C11 C10 C13 C14 -98.7(2) . . . . ?
C17 C16 C21 C20 0.7(3) . . . . ?
C17 C16 C21 C22 178.67(18) . . . . ?
C19 C20 C21 C16 -0.7(3) . . . . ?
C19 C20 C21 C22 -178.63(18) . . . . ?
C23 C22 C21 C16 137.64(19) . . . . ?
C26 C22 C21 C16 -42.4(2) . . . . ?
C23 C22 C21 C20 -44.4(3) . . . . ?
C26 C22 C21 C20 135.51(19) . . . . ?
N3 C25 C28 C29 -84.3(2) . . . . ?
C26 C25 C28 C29 92.7(2) . . . . ?
C7 C8 C12 N2 -179(100) . . . . ?
C9 C8 C12 N2 -1(7) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C10 C13 C14 C15 -176.46(17) . . . . ?
C20 C19 C18 C17 0.1(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C25 C28 C29 C30 176.80(19) . . . . ?

_diffrn_measured_fraction_theta_max 25.24
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 25.24
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 981430'
