# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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# 
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#  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. 
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data_e:\120912a\work\mo_120912a_0m
_database_code_depnum_ccdc_archive 'CCDC 905791'
#TrackingRef 'web_deposit_cif_file_0_YanYang_1350135055.2-benzoyl-3-(4-chlorobenzoyl)-4H-pyrido[1,2-a]pyrimidin-4-one.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 Cl N2 O3'
_chemical_formula_weight         388.79
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   9.3517(11)
_cell_length_b                   21.188(3)
_cell_length_c                   10.1099(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.796(2)
_cell_angle_gamma                90.00
_cell_volume                     1896.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5365
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.17
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12848
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3716
_reflns_number_gt                2997
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0902P)^2^+0.7185P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.0025(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3716
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.6758(2) 1.08661(9) 0.2313(2) 0.0449(5) Uani 1 1 d . . .
C2 C 0.5896(3) 1.10728(11) 0.0986(2) 0.0612(6) Uani 1 1 d . . .
H2 H 0.5277 1.0790 0.0354 0.073 Uiso 1 1 calc R . .
C3 C 0.5955(4) 1.16914(14) 0.0608(3) 0.0765(8) Uani 1 1 d . . .
H3 H 0.5378 1.1829 -0.0276 0.092 Uiso 1 1 calc R . .
C4 C 0.6876(3) 1.21070(12) 0.1550(3) 0.0681(7) Uani 1 1 d . . .
C5 C 0.7735(3) 1.19172(11) 0.2869(3) 0.0633(6) Uani 1 1 d . . .
H5 H 0.8349 1.2203 0.3497 0.076 Uiso 1 1 calc R . .
C6 C 0.7665(2) 1.12912(10) 0.3244(2) 0.0513(5) Uani 1 1 d . . .
H6 H 0.8237 1.1156 0.4133 0.062 Uiso 1 1 calc R . .
C7 C 0.6746(2) 1.01833(9) 0.26424(19) 0.0444(4) Uani 1 1 d . . .
C8 C 0.7267(2) 0.99603(8) 0.41115(18) 0.0392(4) Uani 1 1 d . . .
C9 C 0.6755(2) 1.02545(9) 0.5149(2) 0.0417(4) Uani 1 1 d . . .
C10 C 0.8312(2) 0.94499(9) 0.6744(2) 0.0469(5) Uani 1 1 d . . .
C11 C 0.8155(2) 0.94262(8) 0.44490(19) 0.0398(4) Uani 1 1 d . . .
C12 C 0.8881(3) 0.92141(12) 0.8118(2) 0.0656(6) Uani 1 1 d . . .
H12 H 0.9528 0.8868 0.8304 0.079 Uiso 1 1 calc R . .
C13 C 0.8498(4) 0.94834(15) 0.9172(2) 0.0757(8) Uani 1 1 d . . .
H13 H 0.8875 0.9322 1.0073 0.091 Uiso 1 1 calc R . .
C14 C 0.7542(4) 1.00010(16) 0.8900(3) 0.0775(8) Uani 1 1 d . . .
H14 H 0.7275 1.0186 0.9621 0.093 Uiso 1 1 calc R . .
C15 C 0.6995(3) 1.02384(13) 0.7591(2) 0.0614(6) Uani 1 1 d . . .
H15 H 0.6358 1.0587 0.7416 0.074 Uiso 1 1 calc R . .
C16 C 0.8742(2) 0.90996(9) 0.3387(2) 0.0434(4) Uani 1 1 d . . .
C17 C 0.8175(2) 0.84618(9) 0.2900(2) 0.0453(5) Uani 1 1 d . . .
C18 C 0.8862(3) 0.81180(13) 0.2099(3) 0.0730(7) Uani 1 1 d . . .
H18 H 0.9679 0.8289 0.1889 0.088 Uiso 1 1 calc R . .
C19 C 0.8338(4) 0.75244(15) 0.1614(4) 0.0925(11) Uani 1 1 d . . .
H19 H 0.8808 0.7297 0.1084 0.111 Uiso 1 1 calc R . .
C20 C 0.7136(4) 0.72706(13) 0.1911(3) 0.0837(9) Uani 1 1 d . . .
H20 H 0.6785 0.6871 0.1581 0.100 Uiso 1 1 calc R . .
C21 C 0.6451(3) 0.76019(12) 0.2687(3) 0.0751(8) Uani 1 1 d . . .
H21 H 0.5634 0.7426 0.2890 0.090 Uiso 1 1 calc R . .
C22 C 0.6954(3) 0.81985(10) 0.3180(2) 0.0577(6) Uani 1 1 d . . .
H22 H 0.6468 0.8422 0.3702 0.069 Uiso 1 1 calc R . .
Cl1 Cl 0.68852(13) 1.28992(4) 0.10904(11) 0.1065(4) Uani 1 1 d . . .
N1 N 0.8682(2) 0.91645(8) 0.57187(17) 0.0482(4) Uani 1 1 d . . .
N2 N 0.73792(18) 0.99649(8) 0.65172(16) 0.0436(4) Uani 1 1 d . . .
O1 O 0.6392(2) 0.97937(7) 0.17025(15) 0.0648(5) Uani 1 1 d . . .
O2 O 0.58735(18) 1.06910(7) 0.50056(16) 0.0554(4) Uani 1 1 d . . .
O3 O 0.9707(2) 0.93635(8) 0.30253(19) 0.0675(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0499(11) 0.0483(10) 0.0383(10) 0.0048(8) 0.0166(8) 0.0087(8)
C2 0.0791(16) 0.0578(13) 0.0400(11) 0.0014(9) 0.0097(11) 0.0138(11)
C3 0.108(2) 0.0688(16) 0.0478(13) 0.0187(12) 0.0179(14) 0.0242(15)
C4 0.0880(18) 0.0520(13) 0.0731(16) 0.0215(12) 0.0382(14) 0.0105(12)
C5 0.0671(15) 0.0541(12) 0.0692(15) 0.0086(11) 0.0227(12) -0.0065(11)
C6 0.0530(12) 0.0527(12) 0.0466(11) 0.0080(9) 0.0137(9) -0.0007(9)
C7 0.0489(11) 0.0470(10) 0.0364(9) -0.0038(8) 0.0127(8) 0.0022(8)
C8 0.0464(10) 0.0377(9) 0.0342(9) -0.0035(7) 0.0140(8) -0.0042(7)
C9 0.0474(10) 0.0404(9) 0.0400(10) -0.0046(7) 0.0177(8) -0.0078(8)
C10 0.0581(12) 0.0445(10) 0.0374(10) -0.0004(8) 0.0144(9) -0.0119(9)
C11 0.0477(10) 0.0364(9) 0.0360(9) -0.0038(7) 0.0143(8) -0.0061(7)
C12 0.0890(18) 0.0634(14) 0.0404(12) 0.0085(10) 0.0151(11) -0.0060(13)
C13 0.102(2) 0.089(2) 0.0369(12) 0.0035(12) 0.0232(13) -0.0173(17)
C14 0.097(2) 0.102(2) 0.0433(13) -0.0125(13) 0.0359(13) -0.0117(17)
C15 0.0704(15) 0.0759(15) 0.0473(12) -0.0127(11) 0.0320(11) -0.0077(12)
C16 0.0462(10) 0.0443(10) 0.0399(10) -0.0023(8) 0.0141(8) 0.0009(8)
C17 0.0530(11) 0.0393(10) 0.0411(10) -0.0014(8) 0.0116(8) 0.0060(8)
C18 0.0636(15) 0.0701(15) 0.0868(18) -0.0288(14) 0.0263(13) 0.0060(12)
C19 0.085(2) 0.0737(19) 0.110(2) -0.0453(18) 0.0190(18) 0.0154(16)
C20 0.090(2) 0.0436(13) 0.093(2) -0.0150(13) -0.0043(17) 0.0077(13)
C21 0.0913(19) 0.0530(14) 0.0749(17) 0.0064(12) 0.0183(15) -0.0193(13)
C22 0.0743(15) 0.0473(12) 0.0545(13) -0.0014(9) 0.0247(11) -0.0077(10)
Cl1 0.1447(8) 0.0625(5) 0.1179(7) 0.0400(4) 0.0499(6) 0.0035(4)
N1 0.0628(11) 0.0417(9) 0.0391(9) 0.0016(7) 0.0149(8) -0.0008(8)
N2 0.0508(9) 0.0482(9) 0.0355(8) -0.0066(7) 0.0191(7) -0.0115(7)
O1 0.0969(13) 0.0530(9) 0.0383(8) -0.0071(7) 0.0131(8) 0.0027(8)
O2 0.0664(10) 0.0477(8) 0.0582(9) -0.0037(7) 0.0287(8) 0.0065(7)
O3 0.0716(11) 0.0686(10) 0.0769(11) -0.0188(8) 0.0443(9) -0.0206(8)
_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 C6 1.380(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.485(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 Cl1 1.742(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.221(2) . ?
C7 C8 1.483(3) . ?
C8 C11 1.380(3) . ?
C8 C9 1.429(2) . ?
C9 O2 1.216(2) . ?
C9 N2 1.453(3) . ?
C10 N1 1.338(3) . ?
C10 N2 1.369(3) . ?
C10 C12 1.409(3) . ?
C11 N1 1.338(2) . ?
C11 C16 1.521(3) . ?
C12 C13 1.355(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.353(4) . ?
C14 H14 0.9300 . ?
C15 N2 1.377(3) . ?
C15 H15 0.9300 . ?
C16 O3 1.213(2) . ?
C16 C17 1.477(3) . ?
C17 C22 1.379(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.381(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
C6 C1 C2 119.3(2) . . ?
C6 C1 C7 122.02(18) . . ?
C2 C1 C7 118.55(19) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 Cl1 119.2(2) . . ?
C5 C4 Cl1 119.2(2) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C8 118.88(18) . . ?
O1 C7 C1 120.23(18) . . ?
C8 C7 C1 120.74(16) . . ?
C11 C8 C9 119.58(16) . . ?
C11 C8 C7 119.10(16) . . ?
C9 C8 C7 121.07(17) . . ?
O2 C9 C8 128.24(18) . . ?
O2 C9 N2 118.93(17) . . ?
C8 C9 N2 112.81(16) . . ?
N1 C10 N2 122.71(17) . . ?
N1 C10 C12 119.6(2) . . ?
N2 C10 C12 117.71(19) . . ?
N1 C11 C8 125.70(17) . . ?
N1 C11 C16 112.54(17) . . ?
C8 C11 C16 121.60(16) . . ?
C13 C12 C10 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C10 C12 H12 119.5 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 N2 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
N2 C15 H15 119.9 . . ?
O3 C16 C17 122.93(18) . . ?
O3 C16 C11 118.39(17) . . ?
C17 C16 C11 118.60(17) . . ?
C22 C17 C18 118.4(2) . . ?
C22 C17 C16 122.28(18) . . ?
C18 C17 C16 119.3(2) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 120.2(2) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C11 N1 C10 116.63(17) . . ?
C10 N2 C15 121.17(18) . . ?
C10 N2 C9 122.33(15) . . ?
C15 N2 C9 116.50(19) . . ?
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 0.3(4) . . . . ?
C7 C1 C2 C3 -175.6(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 Cl1 -177.3(2) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
Cl1 C4 C5 C6 177.1(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C7 C1 C6 C5 175.3(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C7 O1 -154.0(2) . . . . ?
C2 C1 C7 O1 21.8(3) . . . . ?
C6 C1 C7 C8 21.5(3) . . . . ?
C2 C1 C7 C8 -162.7(2) . . . . ?
O1 C7 C8 C11 37.6(3) . . . . ?
C1 C7 C8 C11 -138.01(19) . . . . ?
O1 C7 C8 C9 -136.7(2) . . . . ?
C1 C7 C8 C9 47.7(3) . . . . ?
C11 C8 C9 O2 -173.35(19) . . . . ?
C7 C8 C9 O2 0.9(3) . . . . ?
C11 C8 C9 N2 5.1(2) . . . . ?
C7 C8 C9 N2 179.39(16) . . . . ?
C9 C8 C11 N1 -4.3(3) . . . . ?
C7 C8 C11 N1 -178.69(18) . . . . ?
C9 C8 C11 C16 -179.35(17) . . . . ?
C7 C8 C11 C16 6.3(3) . . . . ?
N1 C10 C12 C13 -178.4(2) . . . . ?
N2 C10 C12 C13 0.9(4) . . . . ?
C10 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C14 C15 N2 0.3(4) . . . . ?
N1 C11 C16 O3 -105.6(2) . . . . ?
C8 C11 C16 O3 70.1(3) . . . . ?
N1 C11 C16 C17 71.2(2) . . . . ?
C8 C11 C16 C17 -113.1(2) . . . . ?
O3 C16 C17 C22 -171.9(2) . . . . ?
C11 C16 C17 C22 11.5(3) . . . . ?
O3 C16 C17 C18 6.4(3) . . . . ?
C11 C16 C17 C18 -170.3(2) . . . . ?
C22 C17 C18 C19 -0.7(4) . . . . ?
C16 C17 C18 C19 -179.1(3) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C16 C17 C22 C21 179.2(2) . . . . ?
C20 C21 C22 C17 -0.7(4) . . . . ?
C8 C11 N1 C10 -0.1(3) . . . . ?
C16 C11 N1 C10 175.30(17) . . . . ?
N2 C10 N1 C11 3.3(3) . . . . ?
C12 C10 N1 C11 -177.41(19) . . . . ?
N1 C10 N2 C15 178.55(19) . . . . ?
C12 C10 N2 C15 -0.8(3) . . . . ?
N1 C10 N2 C9 -2.0(3) . . . . ?
C12 C10 N2 C9 178.70(18) . . . . ?
C14 C15 N2 C10 0.2(3) . . . . ?
C14 C15 N2 C9 -179.3(2) . . . . ?
O2 C9 N2 C10 176.32(18) . . . . ?
C8 C9 N2 C10 -2.3(2) . . . . ?
O2 C9 N2 C15 -4.2(3) . . . . ?
C8 C9 N2 C15 177.20(17) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.043


data_e:\120710i\work\t
_database_code_depnum_ccdc_archive 'CCDC 905792'
#TrackingRef 'web_deposit_cif_file_1_YanYang_1350135055.(Z)-ethyl 2-benzoyl-4-(naphthalen-1-yl)-4-oxo-3-(pyridin-2-ylamino)but-2-enoate.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N2 O4'
_chemical_formula_weight         450.48
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   8.7681(13)
_cell_length_b                   8.9732(14)
_cell_length_c                   16.456(3)
_cell_angle_alpha                86.719(2)
_cell_angle_beta                 88.205(2)
_cell_angle_gamma                64.921(2)
_cell_volume                     1170.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.14
_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9897
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7988
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4031
_reflns_number_gt                3710
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0646P)^2^+1.1474P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4031
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1800
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5842(3) 0.3041(3) 0.35810(15) 0.0391(6) Uani 1 1 d . . .
C2 C 0.4511(4) 0.3171(4) 0.40742(18) 0.0548(8) Uani 1 1 d . . .
H2 H 0.3491 0.3354 0.3840 0.066 Uiso 1 1 calc R . .
C3 C 0.4650(5) 0.3033(6) 0.4927(2) 0.0745(11) Uani 1 1 d . . .
H3 H 0.3732 0.3123 0.5253 0.089 Uiso 1 1 calc R . .
C4 C 0.6127(5) 0.2770(5) 0.5268(2) 0.0729(10) Uani 1 1 d . . .
H4 H 0.6211 0.2701 0.5832 0.087 Uiso 1 1 calc R . .
C5 C 0.7547(4) 0.2598(4) 0.47876(18) 0.0573(8) Uani 1 1 d . . .
C6 C 0.7435(3) 0.2719(3) 0.39257(16) 0.0419(6) Uani 1 1 d . . .
C7 C 0.8907(4) 0.2465(4) 0.34639(19) 0.0532(7) Uani 1 1 d . . .
H7 H 0.8871 0.2508 0.2899 0.064 Uiso 1 1 calc R . .
C8 C 1.0377(5) 0.2158(6) 0.3845(3) 0.0774(11) Uani 1 1 d . . .
H8 H 1.1336 0.1993 0.3535 0.093 Uiso 1 1 calc R . .
C9 C 1.0466(5) 0.2087(6) 0.4699(3) 0.0902(14) Uani 1 1 d . . .
H9 H 1.1472 0.1899 0.4949 0.108 Uiso 1 1 calc R . .
C10 C 0.9096(6) 0.2292(6) 0.5153(2) 0.0841(13) Uani 1 1 d . . .
H10 H 0.9169 0.2232 0.5717 0.101 Uiso 1 1 calc R . .
C11 C 0.5542(3) 0.3335(3) 0.26915(15) 0.0372(6) Uani 1 1 d . . .
C12 C 0.4115(3) 0.3017(3) 0.23451(15) 0.0377(6) Uani 1 1 d . . .
C13 C 0.5624(3) 0.0017(3) 0.26108(16) 0.0409(6) Uani 1 1 d . . .
C14 C 0.5437(4) -0.1435(4) 0.27739(18) 0.0498(7) Uani 1 1 d . . .
H14 H 0.4396 -0.1466 0.2729 0.060 Uiso 1 1 calc R . .
C15 C 0.6851(4) -0.2828(4) 0.30043(19) 0.0577(8) Uani 1 1 d . . .
H15 H 0.6776 -0.3820 0.3123 0.069 Uiso 1 1 calc R . .
C16 C 0.8373(4) -0.2741(4) 0.30578(19) 0.0609(9) Uani 1 1 d . . .
H16 H 0.9338 -0.3666 0.3213 0.073 Uiso 1 1 calc R . .
C17 C 0.8431(4) -0.1263(4) 0.2877(2) 0.0582(8) Uani 1 1 d . . .
H17 H 0.9459 -0.1206 0.2923 0.070 Uiso 1 1 calc R . .
C18 C 0.2784(3) 0.4319(3) 0.19980(15) 0.0381(6) Uani 1 1 d . . .
C19 C 0.2667(3) 0.6037(3) 0.20297(16) 0.0394(6) Uani 1 1 d . . .
C20 C 0.2560(3) 0.7014(3) 0.12607(16) 0.0409(6) Uani 1 1 d . . .
C21 C 0.3055(4) 0.6273(4) 0.05240(17) 0.0487(7) Uani 1 1 d . . .
H21 H 0.3423 0.5139 0.0505 0.058 Uiso 1 1 calc R . .
C22 C 0.3010(5) 0.7195(4) -0.01842(19) 0.0612(8) Uani 1 1 d . . .
H22 H 0.3364 0.6681 -0.0674 0.073 Uiso 1 1 calc R . .
C23 C 0.2446(6) 0.8858(5) -0.0161(2) 0.0812(12) Uani 1 1 d . . .
H23 H 0.2404 0.9481 -0.0638 0.097 Uiso 1 1 calc R . .
C24 C 0.1933(7) 0.9630(5) 0.0567(2) 0.0871(13) Uani 1 1 d . . .
H24 H 0.1536 1.0768 0.0577 0.105 Uiso 1 1 calc R . .
C25 C 0.2012(5) 0.8710(4) 0.1277(2) 0.0617(9) Uani 1 1 d . . .
H25 H 0.1699 0.9225 0.1769 0.074 Uiso 1 1 calc R . .
C26 C 0.1380(3) 0.4075(3) 0.16634(16) 0.0405(6) Uani 1 1 d . . .
C27 C -0.1305(4) 0.5328(4) 0.1054(2) 0.0528(7) Uani 1 1 d . . .
H27A H -0.1834 0.4944 0.1493 0.063 Uiso 1 1 calc R . .
H27B H -0.0985 0.4547 0.0627 0.063 Uiso 1 1 calc R . .
C28 C -0.2488(4) 0.6983(4) 0.0733(2) 0.0649(9) Uani 1 1 d . . .
H28A H -0.2699 0.7769 0.1143 0.097 Uiso 1 1 calc R . .
H28B H -0.3528 0.6956 0.0589 0.097 Uiso 1 1 calc R . .
H28C H -0.2002 0.7296 0.0260 0.097 Uiso 1 1 calc R . .
N1 N 0.7089(3) 0.0120(3) 0.26359(15) 0.0495(6) Uani 1 1 d . . .
N2 N 0.4222(3) 0.1461(3) 0.23883(14) 0.0451(6) Uani 1 1 d . . .
H2A H 0.3329 0.1353 0.2265 0.054 Uiso 1 1 calc R . .
O1 O 0.6248(2) 0.3949(3) 0.22327(11) 0.0488(5) Uani 1 1 d . . .
O2 O 0.2687(3) 0.6602(2) 0.26853(12) 0.0533(5) Uani 1 1 d . . .
O3 O 0.1273(3) 0.2765(2) 0.16751(14) 0.0562(6) Uani 1 1 d . . .
O4 O 0.0170(2) 0.5468(2) 0.13509(12) 0.0479(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0443(14) 0.0409(13) 0.0370(13) -0.0013(10) -0.0019(11) -0.0228(11)
C2 0.0505(16) 0.081(2) 0.0423(16) -0.0049(14) 0.0024(12) -0.0364(16)
C3 0.079(2) 0.123(3) 0.0408(17) -0.0088(18) 0.0115(16) -0.061(2)
C4 0.091(3) 0.106(3) 0.0366(16) 0.0000(17) -0.0014(16) -0.056(2)
C5 0.069(2) 0.071(2) 0.0437(16) 0.0060(14) -0.0131(14) -0.0405(17)
C6 0.0474(15) 0.0411(14) 0.0423(14) 0.0000(11) -0.0058(11) -0.0234(12)
C7 0.0459(16) 0.0648(19) 0.0530(17) 0.0001(14) -0.0032(13) -0.0275(14)
C8 0.0517(19) 0.106(3) 0.080(3) 0.006(2) -0.0098(17) -0.039(2)
C9 0.069(2) 0.128(4) 0.086(3) 0.012(3) -0.034(2) -0.054(3)
C10 0.090(3) 0.122(4) 0.059(2) 0.014(2) -0.033(2) -0.062(3)
C11 0.0377(13) 0.0391(13) 0.0376(13) -0.0026(10) 0.0016(10) -0.0190(11)
C12 0.0411(13) 0.0431(14) 0.0341(13) -0.0031(10) 0.0025(10) -0.0228(11)
C13 0.0453(14) 0.0413(14) 0.0372(13) -0.0020(10) -0.0008(11) -0.0194(12)
C14 0.0594(17) 0.0474(16) 0.0498(16) 0.0023(12) -0.0031(13) -0.0297(14)
C15 0.077(2) 0.0427(16) 0.0514(17) 0.0028(13) -0.0026(15) -0.0241(15)
C16 0.064(2) 0.0495(18) 0.0519(18) -0.0039(14) -0.0081(15) -0.0064(15)
C17 0.0462(16) 0.0566(18) 0.063(2) -0.0113(15) -0.0047(14) -0.0124(14)
C18 0.0389(13) 0.0431(14) 0.0360(13) -0.0026(10) -0.0013(10) -0.0209(11)
C19 0.0331(12) 0.0414(14) 0.0440(14) -0.0052(11) -0.0048(10) -0.0153(11)
C20 0.0403(13) 0.0419(14) 0.0439(14) -0.0035(11) -0.0054(11) -0.0200(11)
C21 0.0542(16) 0.0508(16) 0.0471(16) -0.0083(12) 0.0014(12) -0.0274(14)
C22 0.080(2) 0.071(2) 0.0449(17) -0.0025(15) -0.0020(15) -0.0436(19)
C23 0.126(4) 0.071(2) 0.054(2) 0.0146(18) -0.010(2) -0.051(2)
C24 0.142(4) 0.0471(19) 0.070(2) 0.0090(17) -0.014(2) -0.039(2)
C25 0.091(2) 0.0435(16) 0.0497(17) -0.0038(13) -0.0070(16) -0.0269(16)
C26 0.0413(14) 0.0451(15) 0.0391(14) -0.0036(11) -0.0016(11) -0.0219(12)
C27 0.0428(15) 0.0609(18) 0.0632(19) 0.0018(14) -0.0122(13) -0.0299(14)
C28 0.0557(19) 0.067(2) 0.068(2) 0.0032(16) -0.0164(16) -0.0218(16)
N1 0.0461(13) 0.0456(13) 0.0580(15) -0.0045(11) -0.0017(11) -0.0201(11)
N2 0.0435(12) 0.0428(12) 0.0541(14) 0.0013(10) -0.0077(10) -0.0232(10)
O1 0.0515(11) 0.0631(13) 0.0421(10) 0.0064(9) -0.0028(8) -0.0352(10)
O2 0.0707(14) 0.0502(12) 0.0421(11) -0.0101(9) -0.0050(9) -0.0274(10)
O3 0.0551(12) 0.0479(12) 0.0744(15) -0.0007(10) -0.0185(10) -0.0295(10)
O4 0.0415(10) 0.0473(11) 0.0597(12) -0.0001(9) -0.0108(9) -0.0231(9)
_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 1.368(4) . ?
C1 C6 1.429(4) . ?
C1 C11 1.484(3) . ?
C2 C3 1.406(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(5) . ?
C4 H4 0.9300 . ?
C5 C10 1.414(5) . ?
C5 C6 1.420(4) . ?
C6 C7 1.416(4) . ?
C7 C8 1.364(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.406(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.345(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.212(3) . ?
C11 C12 1.529(3) . ?
C12 N2 1.358(3) . ?
C12 C18 1.365(4) . ?
C13 N1 1.328(4) . ?
C13 C14 1.391(4) . ?
C13 N2 1.396(3) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 N1 1.348(4) . ?
C17 H17 0.9300 . ?
C18 C26 1.467(3) . ?
C18 C19 1.505(4) . ?
C19 O2 1.222(3) . ?
C19 C20 1.480(4) . ?
C20 C21 1.384(4) . ?
C20 C25 1.390(4) . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.362(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O3 1.217(3) . ?
C26 O4 1.337(3) . ?
C27 O4 1.454(3) . ?
C27 C28 1.483(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N2 H2A 0.8600 . ?
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 120.3(2) . . ?
C2 C1 C11 117.7(2) . . ?
C6 C1 C11 121.9(2) . . ?
C1 C2 C3 121.5(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C10 120.8(3) . . ?
C4 C5 C6 120.0(3) . . ?
C10 C5 C6 119.2(3) . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 C1 124.2(2) . . ?
C5 C6 C1 117.4(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
O1 C11 C1 124.4(2) . . ?
O1 C11 C12 117.5(2) . . ?
C1 C11 C12 117.8(2) . . ?
N2 C12 C18 122.6(2) . . ?
N2 C12 C11 119.1(2) . . ?
C18 C12 C11 118.3(2) . . ?
N1 C13 C14 123.8(3) . . ?
N1 C13 N2 116.7(2) . . ?
C14 C13 N2 119.5(2) . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 118.3(3) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N1 C17 C16 124.0(3) . . ?
N1 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
C12 C18 C26 120.2(2) . . ?
C12 C18 C19 120.1(2) . . ?
C26 C18 C19 119.4(2) . . ?
O2 C19 C20 120.7(2) . . ?
O2 C19 C18 120.0(2) . . ?
C20 C19 C18 119.3(2) . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C19 121.6(2) . . ?
C25 C20 C19 119.6(2) . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
O3 C26 O4 122.1(2) . . ?
O3 C26 C18 124.9(2) . . ?
O4 C26 C18 113.0(2) . . ?
O4 C27 C28 107.6(2) . . ?
O4 C27 H27A 110.2 . . ?
C28 C27 H27A 110.2 . . ?
O4 C27 H27B 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 N1 C17 116.5(3) . . ?
C12 N2 C13 127.0(2) . . ?
C12 N2 H2A 116.5 . . ?
C13 N2 H2A 116.5 . . ?
C26 O4 C27 115.7(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.5(5) . . . . ?
C11 C1 C2 C3 -175.2(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C10 -178.8(4) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C7 -177.2(3) . . . . ?
C10 C5 C6 C7 2.4(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C10 C5 C6 C1 -179.6(3) . . . . ?
C2 C1 C6 C7 176.0(3) . . . . ?
C11 C1 C6 C7 -7.4(4) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C11 C1 C6 C5 174.6(3) . . . . ?
C5 C6 C7 C8 -1.8(5) . . . . ?
C1 C6 C7 C8 -179.7(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 1.3(7) . . . . ?
C8 C9 C10 C5 -0.7(8) . . . . ?
C4 C5 C10 C9 178.4(4) . . . . ?
C6 C5 C10 C9 -1.2(6) . . . . ?
C2 C1 C11 O1 146.8(3) . . . . ?
C6 C1 C11 O1 -29.8(4) . . . . ?
C2 C1 C11 C12 -26.2(4) . . . . ?
C6 C1 C11 C12 157.1(2) . . . . ?
O1 C11 C12 N2 122.2(3) . . . . ?
C1 C11 C12 N2 -64.3(3) . . . . ?
O1 C11 C12 C18 -57.4(3) . . . . ?
C1 C11 C12 C18 116.1(3) . . . . ?
N1 C13 C14 C15 2.5(4) . . . . ?
N2 C13 C14 C15 -179.0(3) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 N1 -1.1(5) . . . . ?
N2 C12 C18 C26 0.9(4) . . . . ?
C11 C12 C18 C26 -179.5(2) . . . . ?
N2 C12 C18 C19 174.9(2) . . . . ?
C11 C12 C18 C19 -5.5(3) . . . . ?
C12 C18 C19 O2 -56.5(3) . . . . ?
C26 C18 C19 O2 117.5(3) . . . . ?
C12 C18 C19 C20 122.3(3) . . . . ?
C26 C18 C19 C20 -63.6(3) . . . . ?
O2 C19 C20 C21 159.4(3) . . . . ?
C18 C19 C20 C21 -19.5(4) . . . . ?
O2 C19 C20 C25 -18.0(4) . . . . ?
C18 C19 C20 C25 163.1(3) . . . . ?
C25 C20 C21 C22 0.0(4) . . . . ?
C19 C20 C21 C22 -177.4(3) . . . . ?
C20 C21 C22 C23 -1.1(5) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C22 C23 C24 C25 0.8(7) . . . . ?
C23 C24 C25 C20 -1.8(7) . . . . ?
C21 C20 C25 C24 1.4(5) . . . . ?
C19 C20 C25 C24 178.9(3) . . . . ?
C12 C18 C26 O3 1.0(4) . . . . ?
C19 C18 C26 O3 -173.0(3) . . . . ?
C12 C18 C26 O4 179.5(2) . . . . ?
C19 C18 C26 O4 5.5(3) . . . . ?
C14 C13 N1 C17 -3.6(4) . . . . ?
N2 C13 N1 C17 177.9(2) . . . . ?
C16 C17 N1 C13 2.9(5) . . . . ?
C18 C12 N2 C13 169.2(3) . . . . ?
C11 C12 N2 C13 -10.3(4) . . . . ?
N1 C13 N2 C12 -13.6(4) . . . . ?
C14 C13 N2 C12 167.8(3) . . . . ?
O3 C26 O4 C27 2.2(4) . . . . ?
C18 C26 O4 C27 -176.4(2) . . . . ?
C28 C27 O4 C26 -179.9(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O3 0.86 1.96 2.627(3) 133.8 .
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049