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


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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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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#  fide research purposes only. It may contain copyright material 
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data_new
_database_code_depnum_ccdc_archive 'CCDC 907117'
#TrackingRef '1599.cif.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N5 O3'
_chemical_formula_sum            'C17 H19 N5 O3'
_chemical_formula_weight         341.37
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '
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                   10.2755(5)
_cell_length_b                   18.0150(9)
_cell_length_c                   10.8800(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.623(2)
_cell_angle_gamma                90.00
_cell_volume                     1800.49(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9583
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   ' SADABS(Bruker,2004)'
_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 ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11735
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         28.33
_reflns_number_total             4167
_reflns_number_gt                2732
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       APEXII,Bruker,2004
_computing_cell_refinement       APEXII,Bruker,2004
_computing_data_reduction        SAINT,Bruker,2004
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0689P)^2^+0.3536P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4167
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.66577(19) 0.66805(10) 0.13174(19) 0.0539(5) Uani 1 1 d . . .
C2 C 0.5645(2) 0.66080(10) 0.1817(2) 0.0620(5) Uani 1 1 d . . .
H2 H 0.5573 0.6166 0.2225 0.074 Uiso 1 1 calc R . .
C3 C 0.4743(2) 0.71954(9) 0.17074(19) 0.0531(4) Uani 1 1 d . . .
H3 H 0.4063 0.7149 0.2048 0.064 Uiso 1 1 calc R . .
C4 C 0.48335(17) 0.78520(8) 0.10996(16) 0.0398(4) Uani 1 1 d . . .
C5 C 0.58831(19) 0.79233(10) 0.0638(2) 0.0525(4) Uani 1 1 d . . .
H5 H 0.5980 0.8371 0.0259 0.063 Uiso 1 1 calc R . .
C6 C 0.67825(19) 0.73388(10) 0.0733(2) 0.0587(5) Uani 1 1 d . . .
H6 H 0.7473 0.7387 0.0405 0.070 Uiso 1 1 calc R . .
C7 C 0.37709(17) 0.84713(8) 0.09108(16) 0.0403(4) Uani 1 1 d . . .
H7 H 0.3139 0.8327 0.1329 0.048 Uiso 1 1 calc R . .
C8 C 0.28246(16) 0.86836(8) -0.06028(15) 0.0395(4) Uani 1 1 d . . .
H8 H 0.3381 0.8586 -0.1119 0.047 Uiso 1 1 calc R . .
C9 C 0.3766(2) 0.97545(9) 0.06613(18) 0.0519(4) Uani 1 1 d . . .
C10 C 0.13846(18) 0.82699(9) -0.12937(17) 0.0454(4) Uani 1 1 d . . .
H10 H 0.0780 0.8493 -0.2193 0.054 Uiso 1 1 calc R . .
C11 C 0.16607(19) 0.74568(10) -0.14830(18) 0.0505(4) Uani 1 1 d . . .
C12 C 0.0317(2) 0.74968(12) -0.0296(2) 0.0608(5) Uani 1 1 d . . .
C13 C 0.7558(2) 0.60534(12) 0.1368(2) 0.0712(6) Uani 1 1 d . . .
C14 C 0.2105(2) 0.99272(11) -0.1765(2) 0.0748(6) Uani 1 1 d . . .
H14A H 0.2279 1.0443 -0.1527 0.112 Uiso 1 1 calc R . .
H14B H 0.1077 0.9843 -0.2276 0.112 Uiso 1 1 calc R . .
H14C H 0.2580 0.9790 -0.2316 0.112 Uiso 1 1 calc R . .
C15 C 0.5285(3) 0.92512(12) 0.2971(2) 0.0794(7) Uani 1 1 d . . .
H15A H 0.5590 0.9758 0.3192 0.119 Uiso 1 1 calc R . .
H15B H 0.6126 0.8935 0.3304 0.119 Uiso 1 1 calc R . .
H15C H 0.4678 0.9114 0.3394 0.119 Uiso 1 1 calc R . .
C16 C 0.1052(3) 0.62422(13) -0.0779(3) 0.1012(9) Uani 1 1 d . . .
H16A H 0.0917 0.6034 -0.1640 0.152 Uiso 1 1 calc R . .
H16B H 0.0290 0.6072 -0.0567 0.152 Uiso 1 1 calc R . .
H16C H 0.1977 0.6089 -0.0066 0.152 Uiso 1 1 calc R . .
C17 C -0.0045(2) 0.88242(14) -0.0080(2) 0.0786(7) Uani 1 1 d . . .
H17A H -0.0911 0.8668 -0.0028 0.118 Uiso 1 1 calc R . .
H17B H -0.0276 0.9223 -0.0730 0.118 Uiso 1 1 calc R . .
H17C H 0.0661 0.8991 0.0808 0.118 Uiso 1 1 calc R . .
N1 N 0.8254(2) 0.55639(12) 0.1395(3) 0.1038(8) Uani 1 1 d . . .
N2 N 0.26771(16) 0.94828(7) -0.05198(15) 0.0510(4) Uani 1 1 d . . .
N3 N 0.44782(17) 0.91720(7) 0.14986(14) 0.0501(4) Uani 1 1 d . . .
N4 N 0.10080(17) 0.70488(9) -0.08749(18) 0.0618(4) Uani 1 1 d . . .
N5 N 0.05453(16) 0.82098(9) -0.05191(16) 0.0557(4) Uani 1 1 d . . .
O1 O 0.40605(18) 1.04108(7) 0.09364(15) 0.0756(5) Uani 1 1 d . . .
O2 O 0.23672(16) 0.72195(7) -0.20344(14) 0.0679(4) Uani 1 1 d . . .
O3 O -0.03501(17) 0.72567(10) 0.03011(18) 0.0887(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 0.0495(10) 0.0457(10) 0.0541(10) -0.0011(8) 0.0123(8) 0.0127(8)
C2 0.0820(13) 0.0396(10) 0.0677(12) 0.0193(9) 0.0365(11) 0.0122(9)
C3 0.0665(11) 0.0436(9) 0.0609(11) 0.0157(8) 0.0390(9) 0.0075(8)
C4 0.0449(8) 0.0334(8) 0.0423(8) 0.0030(6) 0.0206(7) 0.0005(6)
C5 0.0518(10) 0.0413(9) 0.0728(12) 0.0094(8) 0.0356(9) -0.0004(8)
C6 0.0465(9) 0.0575(11) 0.0789(13) 0.0031(10) 0.0342(9) 0.0048(8)
C7 0.0505(9) 0.0345(8) 0.0433(8) 0.0028(6) 0.0275(7) 0.0017(7)
C8 0.0486(9) 0.0340(8) 0.0425(8) 0.0029(6) 0.0264(7) 0.0043(7)
C9 0.0756(12) 0.0360(9) 0.0516(10) -0.0008(8) 0.0351(9) 0.0021(8)
C10 0.0478(9) 0.0485(9) 0.0448(9) -0.0018(7) 0.0251(7) 0.0021(7)
C11 0.0532(10) 0.0518(10) 0.0503(10) -0.0091(8) 0.0266(8) -0.0083(8)
C12 0.0469(10) 0.0751(13) 0.0661(12) -0.0043(10) 0.0303(9) -0.0130(9)
C13 0.0623(12) 0.0594(12) 0.0688(13) -0.0035(10) 0.0090(10) 0.0184(10)
C14 0.0842(14) 0.0509(11) 0.0707(13) 0.0248(10) 0.0181(11) 0.0048(10)
C15 0.1200(19) 0.0655(13) 0.0422(11) -0.0067(9) 0.0269(12) -0.0087(12)
C16 0.134(2) 0.0523(14) 0.127(2) -0.0106(14) 0.067(2) -0.0278(14)
C17 0.0707(13) 0.0960(17) 0.0824(15) -0.0062(13) 0.0462(12) 0.0245(12)
N1 0.0862(14) 0.0778(14) 0.1162(18) -0.0124(12) 0.0175(13) 0.0395(12)
N2 0.0655(9) 0.0331(7) 0.0532(9) 0.0086(6) 0.0256(8) 0.0068(6)
N3 0.0742(9) 0.0353(7) 0.0398(7) -0.0015(6) 0.0247(7) 0.0000(7)
N4 0.0699(10) 0.0499(9) 0.0756(11) -0.0094(8) 0.0415(9) -0.0132(8)
N5 0.0501(8) 0.0633(10) 0.0645(10) -0.0051(8) 0.0354(7) 0.0039(7)
O1 0.1227(13) 0.0319(7) 0.0720(9) -0.0064(6) 0.0434(9) -0.0040(7)
O2 0.0821(9) 0.0640(9) 0.0749(9) -0.0211(7) 0.0505(8) -0.0021(7)
O3 0.0753(10) 0.1131(14) 0.1017(12) 0.0026(10) 0.0610(10) -0.0213(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 C6 1.378(3) . ?
C1 C2 1.379(3) . ?
C1 C13 1.446(3) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 C7 1.509(2) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N3 1.454(2) . ?
C7 C8 1.539(2) . ?
C7 H7 0.9800 . ?
C8 N2 1.455(2) . ?
C8 C10 1.521(2) . ?
C8 H8 0.9800 . ?
C9 O1 1.224(2) . ?
C9 N2 1.362(2) . ?
C9 N3 1.367(2) . ?
C10 N5 1.455(2) . ?
C10 C11 1.524(2) . ?
C10 H10 0.9800 . ?
C11 O2 1.208(2) . ?
C11 N4 1.351(2) . ?
C12 O3 1.216(2) . ?
C12 N5 1.347(3) . ?
C12 N4 1.398(2) . ?
C13 N1 1.127(3) . ?
C14 N2 1.452(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.443(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N4 1.456(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N5 1.442(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C6 C1 C2 120.39(15) . . ?
C6 C1 C13 119.98(18) . . ?
C2 C1 C13 119.60(18) . . ?
C3 C2 C1 119.38(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.92(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.99(15) . . ?
C3 C4 C7 119.95(14) . . ?
C5 C4 C7 121.03(13) . . ?
C6 C5 C4 120.55(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.73(17) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N3 C7 C4 113.17(13) . . ?
N3 C7 C8 101.92(12) . . ?
C4 C7 C8 113.64(12) . . ?
N3 C7 H7 109.3 . . ?
C4 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
N2 C8 C10 114.23(13) . . ?
N2 C8 C7 102.30(12) . . ?
C10 C8 C7 114.54(12) . . ?
N2 C8 H8 108.5 . . ?
C10 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O1 C9 N2 125.91(17) . . ?
O1 C9 N3 125.36(18) . . ?
N2 C9 N3 108.72(14) . . ?
N5 C10 C8 116.62(13) . . ?
N5 C10 C11 101.62(13) . . ?
C8 C10 C11 109.82(13) . . ?
N5 C10 H10 109.5 . . ?
C8 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
O2 C11 N4 126.24(18) . . ?
O2 C11 C10 126.65(16) . . ?
N4 C11 C10 107.07(14) . . ?
O3 C12 N5 128.4(2) . . ?
O3 C12 N4 123.9(2) . . ?
N5 C12 N4 107.74(15) . . ?
N1 C13 C1 179.4(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 H17A 109.5 . . ?
N5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 N2 C14 120.02(15) . . ?
C9 N2 C8 110.48(13) . . ?
C14 N2 C8 119.84(15) . . ?
C9 N3 C15 122.24(15) . . ?
C9 N3 C7 111.13(14) . . ?
C15 N3 C7 119.96(14) . . ?
C11 N4 C12 111.75(16) . . ?
C11 N4 C16 124.89(18) . . ?
C12 N4 C16 123.33(18) . . ?
C12 N5 C17 122.63(16) . . ?
C12 N5 C10 111.81(14) . . ?
C17 N5 C10 125.50(16) . . ?
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 1.1(3) . . . . ?
C13 C1 C2 C3 -176.92(18) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -2.1(3) . . . . ?
C2 C3 C4 C7 176.18(17) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
C7 C4 C5 C6 -175.71(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C13 C1 C6 C5 177.35(18) . . . . ?
C3 C4 C7 N3 125.75(16) . . . . ?
C5 C4 C7 N3 -56.0(2) . . . . ?
C3 C4 C7 C8 -118.63(17) . . . . ?
C5 C4 C7 C8 59.6(2) . . . . ?
N3 C7 C8 N2 -22.21(15) . . . . ?
C4 C7 C8 N2 -144.30(13) . . . . ?
N3 C7 C8 C10 -146.35(13) . . . . ?
C4 C7 C8 C10 91.56(15) . . . . ?
N2 C8 C10 N5 -72.03(18) . . . . ?
C7 C8 C10 N5 45.49(19) . . . . ?
N2 C8 C10 C11 173.12(13) . . . . ?
C7 C8 C10 C11 -69.35(16) . . . . ?
N5 C10 C11 O2 -177.33(17) . . . . ?
C8 C10 C11 O2 -53.2(2) . . . . ?
N5 C10 C11 N4 0.59(17) . . . . ?
C8 C10 C11 N4 124.67(15) . . . . ?
C6 C1 C13 N1 -66(26) . . . . ?
C2 C1 C13 N1 112(26) . . . . ?
O1 C9 N2 C14 23.0(3) . . . . ?
N3 C9 N2 C14 -157.29(17) . . . . ?
O1 C9 N2 C8 169.04(17) . . . . ?
N3 C9 N2 C8 -11.26(19) . . . . ?
C10 C8 N2 C9 145.62(14) . . . . ?
C7 C8 N2 C9 21.28(17) . . . . ?
C10 C8 N2 C14 -68.3(2) . . . . ?
C7 C8 N2 C14 167.38(16) . . . . ?
O1 C9 N3 C15 23.7(3) . . . . ?
N2 C9 N3 C15 -156.05(18) . . . . ?
O1 C9 N3 C7 174.91(17) . . . . ?
N2 C9 N3 C7 -4.80(19) . . . . ?
C4 C7 N3 C9 139.77(14) . . . . ?
C8 C7 N3 C9 17.36(17) . . . . ?
C4 C7 N3 C15 -68.2(2) . . . . ?
C8 C7 N3 C15 169.35(17) . . . . ?
O2 C11 N4 C12 178.03(18) . . . . ?
C10 C11 N4 C12 0.1(2) . . . . ?
O2 C11 N4 C16 0.2(3) . . . . ?
C10 C11 N4 C16 -177.8(2) . . . . ?
O3 C12 N4 C11 179.63(18) . . . . ?
N5 C12 N4 C11 -0.8(2) . . . . ?
O3 C12 N4 C16 -2.5(3) . . . . ?
N5 C12 N4 C16 177.1(2) . . . . ?
O3 C12 N5 C17 -1.8(3) . . . . ?
N4 C12 N5 C17 178.67(17) . . . . ?
O3 C12 N5 C10 -179.24(19) . . . . ?
N4 C12 N5 C10 1.2(2) . . . . ?
C8 C10 N5 C12 -120.49(17) . . . . ?
C11 C10 N5 C12 -1.13(18) . . . . ?
C8 C10 N5 C17 62.2(2) . . . . ?
C11 C10 N5 C17 -178.47(17) . . . . ?
_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036


data_new2
_database_code_depnum_ccdc_archive 'CCDC 907118'
#TrackingRef '1668.cif.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N4 O4'
_chemical_formula_sum            'C14 H18 N4 O4'
_chemical_formula_weight         306.32
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   6.6929(3)
_cell_length_b                   9.8842(6)
_cell_length_c                   22.5275(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.236(3)
_cell_angle_gamma                90.00
_cell_volume                     1478.41(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3654
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.57
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   'SADABS (Bruker,2004)'
_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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16483
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.34
_reflns_number_total             2972
_reflns_number_gt                1961
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       APEXII,Bruker,2004
_computing_cell_refinement       APEXII,Bruker,2004
_computing_data_reduction        SAINT,Bruker,2004
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0558P)^2^+0.3273P] 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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0052(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2972
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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 0.6025(3) 0.7423(2) 0.14263(9) 0.0426(5) Uani 1 1 d . . .
C2 C 0.6144(3) 0.7332(2) 0.07653(9) 0.0464(5) Uani 1 1 d . . .
H2A H 0.6752 0.8144 0.0626 0.056 Uiso 1 1 calc R . .
H2B H 0.4809 0.7229 0.0547 0.056 Uiso 1 1 calc R . .
C3 C 0.7422(3) 0.6111(2) 0.06733(8) 0.0401(5) Uani 1 1 d . . .
H3 H 0.6851 0.5585 0.0324 0.048 Uiso 1 1 calc R . .
C4 C 1.0750(3) 0.5493(2) 0.09699(9) 0.0421(5) Uani 1 1 d . . .
C5 C 0.7562(3) 0.52611(18) 0.12507(8) 0.0370(4) Uani 1 1 d . . .
H5 H 0.6550 0.4539 0.1216 0.044 Uiso 1 1 calc R . .
C6 C 0.7215(3) 0.62634(19) 0.17495(8) 0.0373(4) Uani 1 1 d . . .
H6 H 0.8532 0.6622 0.1916 0.045 Uiso 1 1 calc R . .
C7 C 1.0192(3) 0.7171(2) 0.01594(9) 0.0589(6) Uani 1 1 d . . .
H7A H 1.1634 0.7136 0.0184 0.088 Uiso 1 1 calc R . .
H7B H 0.9768 0.8095 0.0181 0.088 Uiso 1 1 calc R . .
H7C H 0.9606 0.6784 -0.0213 0.088 Uiso 1 1 calc R . .
C8 C 1.0464(3) 0.3946(2) 0.18040(11) 0.0607(6) Uani 1 1 d . . .
H8A H 1.1738 0.3584 0.1727 0.091 Uiso 1 1 calc R . .
H8B H 0.9579 0.3219 0.1878 0.091 Uiso 1 1 calc R . .
H8C H 1.0661 0.4528 0.2148 0.091 Uiso 1 1 calc R . .
C9 C 0.6241(3) 0.5701(2) 0.22532(8) 0.0397(5) Uani 1 1 d . . .
H9 H 0.5043 0.5227 0.2158 0.048 Uiso 1 1 calc R . .
C10 C 0.6947(3) 0.58192(18) 0.28290(8) 0.0372(4) Uani 1 1 d . . .
C11 C 0.8833(3) 0.64872(19) 0.31008(9) 0.0412(5) Uani 1 1 d . . .
C12 C 0.7137(3) 0.5676(2) 0.38433(9) 0.0495(5) Uani 1 1 d . . .
C13 C 1.0457(4) 0.6798(3) 0.41526(10) 0.0720(7) Uani 1 1 d . . .
H13A H 1.1119 0.6012 0.4335 0.108 Uiso 1 1 calc R . .
H13B H 0.9925 0.7329 0.4453 0.108 Uiso 1 1 calc R . .
H13C H 1.1406 0.7329 0.3967 0.108 Uiso 1 1 calc R . .
C14 C 0.4148(3) 0.4603(2) 0.32684(10) 0.0597(6) Uani 1 1 d . . .
H14A H 0.3918 0.4295 0.3658 0.090 Uiso 1 1 calc R . .
H14B H 0.4212 0.3840 0.3008 0.090 Uiso 1 1 calc R . .
H14C H 0.3066 0.5187 0.3108 0.090 Uiso 1 1 calc R . .
N1 N 0.9544(2) 0.64138(17) 0.06509(7) 0.0443(4) Uani 1 1 d . . .
N2 N 0.9585(2) 0.47101(16) 0.12918(7) 0.0416(4) Uani 1 1 d . . .
N3 N 0.8822(2) 0.63780(17) 0.37031(7) 0.0487(4) Uani 1 1 d . . .
N4 N 0.6030(2) 0.53393(17) 0.33140(7) 0.0449(4) Uani 1 1 d . . .
O1 O 0.5147(2) 0.82863(16) 0.16659(7) 0.0696(5) Uani 1 1 d . . .
O2 O 1.2574(2) 0.53739(15) 0.09723(7) 0.0590(4) Uani 1 1 d . . .
O3 O 1.0140(2) 0.70265(16) 0.28575(6) 0.0578(4) Uani 1 1 d . . .
O4 O 0.6761(3) 0.54288(17) 0.43426(7) 0.0696(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 0.0376(10) 0.0433(11) 0.0479(12) 0.0003(10) 0.0088(9) -0.0042(9)
C2 0.0359(10) 0.0568(13) 0.0457(12) 0.0094(10) 0.0025(9) -0.0006(9)
C3 0.0349(9) 0.0514(12) 0.0332(11) -0.0030(9) 0.0019(8) -0.0066(9)
C4 0.0386(11) 0.0466(12) 0.0421(11) -0.0019(9) 0.0091(9) -0.0020(9)
C5 0.0325(9) 0.0410(10) 0.0372(11) -0.0016(8) 0.0033(8) -0.0082(8)
C6 0.0324(9) 0.0446(11) 0.0349(11) -0.0028(8) 0.0042(8) -0.0068(8)
C7 0.0542(13) 0.0777(16) 0.0476(13) 0.0159(12) 0.0179(10) 0.0003(12)
C8 0.0516(12) 0.0583(14) 0.0716(16) 0.0231(12) 0.0053(11) 0.0036(11)
C9 0.0312(9) 0.0485(12) 0.0399(12) -0.0006(9) 0.0061(8) -0.0065(8)
C10 0.0369(10) 0.0396(10) 0.0363(11) -0.0017(8) 0.0094(8) 0.0022(8)
C11 0.0450(11) 0.0424(11) 0.0358(11) -0.0021(9) 0.0040(9) -0.0004(9)
C12 0.0663(14) 0.0460(12) 0.0381(13) -0.0016(9) 0.0138(11) 0.0119(10)
C13 0.0847(17) 0.0815(17) 0.0444(14) -0.0091(13) -0.0133(12) -0.0052(14)
C14 0.0528(13) 0.0686(15) 0.0618(15) 0.0072(12) 0.0230(11) -0.0046(11)
N1 0.0353(8) 0.0595(11) 0.0393(10) 0.0112(8) 0.0088(7) 0.0001(8)
N2 0.0363(8) 0.0430(9) 0.0461(10) 0.0049(8) 0.0079(7) 0.0021(7)
N3 0.0586(11) 0.0525(10) 0.0337(10) -0.0046(8) 0.0003(8) -0.0006(9)
N4 0.0458(9) 0.0521(10) 0.0389(10) 0.0014(8) 0.0132(8) 0.0000(8)
O1 0.0843(11) 0.0541(10) 0.0749(12) -0.0014(8) 0.0272(9) 0.0183(9)
O2 0.0347(8) 0.0696(10) 0.0748(11) 0.0112(8) 0.0153(7) 0.0052(7)
O3 0.0496(8) 0.0740(10) 0.0487(9) -0.0002(8) 0.0012(7) -0.0206(8)
O4 0.1026(13) 0.0726(11) 0.0375(9) 0.0017(8) 0.0246(8) 0.0076(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 O1 1.202(2) . ?
C1 C2 1.504(3) . ?
C1 C6 1.527(3) . ?
C2 C3 1.508(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.458(2) . ?
C3 C5 1.542(3) . ?
C3 H3 0.9800 . ?
C4 O2 1.226(2) . ?
C4 N1 1.360(2) . ?
C4 N2 1.369(2) . ?
C5 N2 1.452(2) . ?
C5 C6 1.537(2) . ?
C5 H5 0.9800 . ?
C6 C9 1.486(2) . ?
C6 H6 0.9800 . ?
C7 N1 1.447(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.441(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.328(2) . ?
C9 H9 0.9300 . ?
C10 N4 1.402(2) . ?
C10 C11 1.487(3) . ?
C11 O3 1.212(2) . ?
C11 N3 1.362(2) . ?
C12 O4 1.208(2) . ?
C12 N4 1.363(3) . ?
C12 N3 1.394(3) . ?
C13 N3 1.454(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N4 1.447(3) . ?
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
O1 C1 C2 125.24(19) . . ?
O1 C1 C6 125.02(19) . . ?
C2 C1 C6 109.74(16) . . ?
C1 C2 C3 106.60(16) . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
N1 C3 C2 114.35(16) . . ?
N1 C3 C5 100.67(14) . . ?
C2 C3 C5 107.17(15) . . ?
N1 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C5 C3 H3 111.4 . . ?
O2 C4 N1 126.24(17) . . ?
O2 C4 N2 125.18(18) . . ?
N1 C4 N2 108.58(15) . . ?
N2 C5 C6 114.88(14) . . ?
N2 C5 C3 102.42(13) . . ?
C6 C5 C3 105.47(15) . . ?
N2 C5 H5 111.2 . . ?
C6 C5 H5 111.2 . . ?
C3 C5 H5 111.2 . . ?
C9 C6 C1 113.12(15) . . ?
C9 C6 C5 115.97(15) . . ?
C1 C6 C5 104.64(14) . . ?
C9 C6 H6 107.6 . . ?
C1 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C6 125.21(17) . . ?
C10 C9 H9 117.4 . . ?
C6 C9 H9 117.4 . . ?
C9 C10 N4 126.50(17) . . ?
C9 C10 C11 128.32(17) . . ?
N4 C10 C11 105.18(16) . . ?
O3 C11 N3 125.44(18) . . ?
O3 C11 C10 129.24(18) . . ?
N3 C11 C10 105.32(16) . . ?
O4 C12 N4 127.6(2) . . ?
O4 C12 N3 125.5(2) . . ?
N4 C12 N3 106.84(16) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 N1 C7 122.33(16) . . ?
C4 N1 C3 111.11(15) . . ?
C7 N1 C3 121.30(15) . . ?
C4 N2 C8 121.20(16) . . ?
C4 N2 C5 110.05(15) . . ?
C8 N2 C5 122.08(15) . . ?
C11 N3 C12 111.78(17) . . ?
C11 N3 C13 124.97(18) . . ?
C12 N3 C13 122.91(18) . . ?
C12 N4 C10 110.85(16) . . ?
C12 N4 C14 123.88(17) . . ?
C10 N4 C14 125.27(17) . . ?
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
O1 C1 C2 C3 178.97(19) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 N1 -95.10(18) . . . . ?
C1 C2 C3 C5 15.54(19) . . . . ?
N1 C3 C5 N2 -25.62(17) . . . . ?
C2 C3 C5 N2 -145.44(15) . . . . ?
N1 C3 C5 C6 94.91(15) . . . . ?
C2 C3 C5 C6 -24.91(18) . . . . ?
O1 C1 C6 C9 38.6(3) . . . . ?
C2 C1 C6 C9 -142.23(16) . . . . ?
O1 C1 C6 C5 165.75(19) . . . . ?
C2 C1 C6 C5 -15.09(18) . . . . ?
N2 C5 C6 C9 -98.59(18) . . . . ?
C3 C5 C6 C9 149.42(15) . . . . ?
N2 C5 C6 C1 136.05(15) . . . . ?
C3 C5 C6 C1 24.06(17) . . . . ?
C1 C6 C9 C10 -111.3(2) . . . . ?
C5 C6 C9 C10 127.8(2) . . . . ?
C6 C9 C10 N4 177.71(17) . . . . ?
C6 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 O3 -2.2(3) . . . . ?
N4 C10 C11 O3 178.3(2) . . . . ?
C9 C10 C11 N3 177.72(19) . . . . ?
N4 C10 C11 N3 -1.74(19) . . . . ?
O2 C4 N1 C7 15.3(3) . . . . ?
N2 C4 N1 C7 -164.68(18) . . . . ?
O2 C4 N1 C3 169.89(19) . . . . ?
N2 C4 N1 C3 -10.0(2) . . . . ?
C2 C3 N1 C4 137.15(17) . . . . ?
C5 C3 N1 C4 22.6(2) . . . . ?
C2 C3 N1 C7 -67.9(2) . . . . ?
C5 C3 N1 C7 177.57(17) . . . . ?
O2 C4 N2 C8 19.7(3) . . . . ?
N1 C4 N2 C8 -160.41(18) . . . . ?
O2 C4 N2 C5 171.52(18) . . . . ?
N1 C4 N2 C5 -8.5(2) . . . . ?
C6 C5 N2 C4 -91.81(18) . . . . ?
C3 C5 N2 C4 21.97(19) . . . . ?
C6 C5 N2 C8 59.8(2) . . . . ?
C3 C5 N2 C8 173.55(18) . . . . ?
O3 C11 N3 C12 -178.60(19) . . . . ?
C10 C11 N3 C12 1.5(2) . . . . ?
O3 C11 N3 C13 -5.1(3) . . . . ?
C10 C11 N3 C13 174.94(19) . . . . ?
O4 C12 N3 C11 179.6(2) . . . . ?
N4 C12 N3 C11 -0.6(2) . . . . ?
O4 C12 N3 C13 5.9(3) . . . . ?
N4 C12 N3 C13 -174.24(19) . . . . ?
O4 C12 N4 C10 179.2(2) . . . . ?
N3 C12 N4 C10 -0.6(2) . . . . ?
O4 C12 N4 C14 0.1(3) . . . . ?
N3 C12 N4 C14 -179.70(17) . . . . ?
C9 C10 N4 C12 -178.02(19) . . . . ?
C11 C10 N4 C12 1.4(2) . . . . ?
C9 C10 N4 C14 1.1(3) . . . . ?
C11 C10 N4 C14 -179.46(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035