# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'He, Yang'
_publ_contact_author_email       heyangqx@yahoo.com.cn

_publ_section_title              
;
Synthesis of Janus type nucleoside analogues
and their preliminary bioactivity
;
loop_
_publ_author_name
'Yang He'
'Haozhe Yang'
'Meiying Pan'
'Dawei Jiang'

# Attachment '- 4-(2, 3-O-isopropylidene--D-ribofuransoyl)amino-5-cyano-6-chloropyrimidine CIFs.txt'

data_cd4
_database_code_depnum_ccdc_archive 'CCDC 785478'
#TrackingRef '- 4-(2, 3-O-isopropylidene--D-ribofuransoyl)amino-5-cyano-6-chloropyrimidine CIFs.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-(2, 3-O-isopropylidene-\^A-D-ribofuransoyl)amino-5-cyano-6-chloropyrimidine
;
_chemical_name_common            
;4-(2, 3-O-isopropylidene-A-D-ribofuransoyl)amino-5-cyano-6-
chloropyrimidine
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Cl N4 O4'
_chemical_formula_weight         326.74

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   'P 21'

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

_cell_length_a                   10.019(2)
_cell_length_b                   6.5258(13)
_cell_length_c                   22.940(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1470.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5353
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9246
_exptl_absorpt_correction_T_max  0.9375
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         rotating-anode
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12257
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.87
_reflns_number_total             6775
_reflns_number_gt                6332
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear(Rigaku/MSC inc.,2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_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 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 w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.1160P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0234(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_chemical_absolute-configuration unk
_refine_ls_number_reflns         6775
_refine_ls_number_parameters     412
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.04097(5) 0.38940(8) 0.85671(2) 0.02501(12) Uani 1 d . . .
O1 O 0.42475(13) 0.2974(2) 0.61467(6) 0.0253(3) Uani 1 d . . .
O2 O 0.39197(15) 0.7216(3) 0.64685(7) 0.0315(4) Uani 1 d . . .
H2o H 0.4297 0.8089 0.6716 0.047 Uiso 1 calc R . .
O3 O 0.29448(14) 0.3492(3) 0.48519(6) 0.0313(4) Uani 1 d . . .
O4 O 0.12536(17) 0.2306(3) 0.52897(6) 0.0471(5) Uani 1 d . . .
N1 N 0.02240(15) 0.0946(3) 0.77929(7) 0.0205(3) Uani 1 d . . .
N2 N 0.13138(16) 0.0919(3) 0.69506(7) 0.0216(3) Uani 1 d . . .
N3 N 0.28315(19) 0.7169(3) 0.79576(8) 0.0298(4) Uani 1 d . . .
N4 N 0.27313(17) 0.3568(3) 0.67881(7) 0.0207(3) Uani 1 d . . .
H4N H 0.302(3) 0.476(4) 0.6856(11) 0.037(7) Uiso 1 d . . .
C1 C 0.08088(18) 0.2729(3) 0.79511(8) 0.0186(4) Uani 1 d . . .
C2 C 0.05265(19) 0.0124(3) 0.72925(8) 0.0224(4) Uani 1 d . . .
H2 H 0.0129 -0.1169 0.7174 0.027 Uiso 1 calc R . .
C3 C 0.19183(18) 0.2730(3) 0.71214(8) 0.0183(4) Uani 1 d . . .
C4 C 0.16953(17) 0.3696(3) 0.76497(7) 0.0180(4) Uani 1 d . . .
C5 C 0.23128(18) 0.5624(3) 0.78303(7) 0.0199(4) Uani 1 d . . .
C6 C 0.28847(19) 0.2700(3) 0.62182(8) 0.0215(4) Uani 1 d . . .
H6 H 0.2668 0.1203 0.6211 0.026 Uiso 1 calc R . .
C7 C 0.19668(19) 0.3758(4) 0.56910(8) 0.0258(4) Uani 1 d . . .
H7 H 0.1335 0.4761 0.5825 0.031 Uiso 1 calc R . .
C8 C 0.29530(19) 0.4818(4) 0.53533(8) 0.0252(4) Uani 1 d . . .
H8 H 0.2680 0.6256 0.5235 0.030 Uiso 1 calc R . .
C9 C 0.43452(19) 0.4680(4) 0.57605(8) 0.0248(4) Uani 1 d . . .
H9 H 0.5021 0.4311 0.5510 0.030 Uiso 1 calc R . .
C10 C 0.4846(2) 0.6591(4) 0.61017(10) 0.0291(5) Uani 1 d . . .
H10A H 0.5752 0.6330 0.6353 0.035 Uiso 1 calc R . .
H10B H 0.4942 0.7704 0.5820 0.035 Uiso 1 calc R . .
C11 C 0.1680(2) 0.2427(4) 0.47343(8) 0.0249(4) Uani 1 d . . .
C12 C 0.0622(2) 0.3545(4) 0.42876(9) 0.0305(5) Uani 1 d . . .
H12A H 0.0546 0.4961 0.4419 0.046 Uiso 1 calc R . .
H12B H -0.0260 0.2856 0.4254 0.046 Uiso 1 calc R . .
H12C H 0.0892 0.3543 0.3900 0.046 Uiso 1 calc R . .
C13 C 0.1950(2) 0.0282(4) 0.45390(12) 0.0435(6) Uani 1 d . . .
H13A H 0.2227 0.0338 0.4153 0.065 Uiso 1 calc R . .
H13B H 0.1120 -0.0541 0.4504 0.065 Uiso 1 calc R . .
H13C H 0.2679 -0.0342 0.4834 0.065 Uiso 1 calc R . .
Cl2 Cl 0.70982(5) 0.07666(8) 0.65303(2) 0.02538(12) Uani 1 d . . .
O5 O 0.61811(13) 0.8195(2) 0.88568(6) 0.0211(3) Uani 1 d . . .
O6 O 0.87394(14) 0.8434(2) 0.84751(6) 0.0242(3) Uani 1 d . . .
H6o H 0.9178 0.9099 0.8262 0.036 Uiso 1 calc R . .
O7 O 0.81017(14) 0.6597(2) 1.01665(6) 0.0253(3) Uani 1 d . . .
O8 O 0.61243(13) 0.4982(2) 0.97569(5) 0.0240(3) Uani 1 d . . .
N5 N 0.54791(16) 0.0285(3) 0.72812(7) 0.0218(4) Uani 1 d . . .
N6 N 0.52983(16) 0.2618(3) 0.80696(7) 0.0201(3) Uani 1 d . . .
N7 N 0.86304(16) 0.5725(3) 0.71083(7) 0.0269(4) Uani 1 d . . .
N8 N 0.65791(16) 0.5570(3) 0.82222(7) 0.0199(3) Uani 1 d . . .
H8N H 0.719(2) 0.635(3) 0.8156(9) 0.016(5) Uiso 1 d . . .
C14 C 0.64027(19) 0.1509(3) 0.71252(8) 0.0208(4) Uani 1 d . . .
C15 C 0.49843(18) 0.0926(3) 0.77538(8) 0.0205(4) Uani 1 d . . .
H15 H 0.4329 0.0058 0.7876 0.025 Uiso 1 calc R . .
C16 C 0.62386(17) 0.3860(3) 0.79078(7) 0.0183(4) Uani 1 d . . .
C17 C 0.68403(19) 0.3328(3) 0.74168(8) 0.0191(4) Uani 1 d . . .
C18 C 0.78356(19) 0.4624(3) 0.72376(8) 0.0206(4) Uani 1 d . . .
C19 C 0.60449(19) 0.6078(3) 0.87541(8) 0.0195(4) Uani 1 d . . .
H19 H 0.5068 0.5659 0.8702 0.023 Uiso 1 calc R . .
C20 C 0.68886(19) 0.5050(3) 0.92983(8) 0.0201(4) Uani 1 d . . .
H20 H 0.7253 0.3682 0.9210 0.024 Uiso 1 calc R . .
C21 C 0.80059(19) 0.6603(3) 0.95388(8) 0.0195(4) Uani 1 d . . .
H21 H 0.8892 0.6224 0.9429 0.023 Uiso 1 calc R . .
C22 C 0.74582(18) 0.8640(3) 0.92543(8) 0.0200(4) Uani 1 d . . .
H22 H 0.7270 0.9566 0.9576 0.024 Uiso 1 calc R . .
C23 C 0.8402(2) 0.9744(3) 0.89204(9) 0.0236(4) Uani 1 d . . .
H23A H 0.7952 1.0998 0.8733 0.028 Uiso 1 calc R . .
H23B H 0.9242 1.0157 0.9201 0.028 Uiso 1 calc R . .
C24 C 0.70686(19) 0.5239(3) 1.03101(8) 0.0226(4) Uani 1 d . . .
C25 C 0.6326(2) 0.6277(4) 1.07382(9) 0.0302(5) Uani 1 d . . .
H25A H 0.5955 0.7586 1.0570 0.045 Uiso 1 calc R . .
H25B H 0.6959 0.6524 1.1115 0.045 Uiso 1 calc R . .
H25C H 0.5581 0.5396 1.0808 0.045 Uiso 1 calc R . .
C26 C 0.7709(3) 0.3225(4) 1.05316(10) 0.0361(5) Uani 1 d . . .
H26A H 0.7000 0.2270 1.0599 0.054 Uiso 1 calc R . .
H26B H 0.8360 0.3444 1.0906 0.054 Uiso 1 calc R . .
H26C H 0.8186 0.2650 1.0235 0.054 Uiso 1 calc R . .

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
Cl1 0.0283(2) 0.0273(3) 0.0217(2) -0.00314(19) 0.01058(18) -0.0028(2)
O1 0.0199(6) 0.0322(8) 0.0245(7) 0.0031(6) 0.0065(6) 0.0027(6)
O2 0.0320(8) 0.0307(9) 0.0342(8) -0.0087(7) 0.0123(7) -0.0092(7)
O3 0.0278(7) 0.0482(11) 0.0188(6) -0.0050(7) 0.0072(6) -0.0148(7)
O4 0.0425(9) 0.0826(14) 0.0171(7) -0.0047(8) 0.0078(7) -0.0409(10)
N1 0.0208(7) 0.0213(8) 0.0196(7) 0.0014(7) 0.0048(6) -0.0014(7)
N2 0.0227(7) 0.0218(9) 0.0201(7) 0.0000(7) 0.0034(6) -0.0022(7)
N3 0.0313(9) 0.0296(11) 0.0291(9) -0.0008(8) 0.0074(8) -0.0064(8)
N4 0.0257(8) 0.0215(10) 0.0157(7) -0.0011(7) 0.0058(6) -0.0049(7)
C1 0.0180(8) 0.0197(10) 0.0177(8) 0.0013(7) 0.0024(7) 0.0017(8)
C2 0.0222(9) 0.0213(10) 0.0228(9) 0.0007(8) 0.0021(7) -0.0026(8)
C3 0.0167(8) 0.0188(10) 0.0182(8) 0.0017(7) 0.0005(7) 0.0003(7)
C4 0.0176(8) 0.0202(10) 0.0154(8) 0.0011(7) 0.0015(6) -0.0014(8)
C5 0.0200(8) 0.0255(11) 0.0145(8) -0.0002(8) 0.0038(7) -0.0009(9)
C6 0.0219(9) 0.0264(11) 0.0173(8) -0.0023(8) 0.0067(7) -0.0030(8)
C7 0.0196(8) 0.0403(13) 0.0172(8) 0.0005(9) 0.0030(7) -0.0033(9)
C8 0.0244(9) 0.0317(12) 0.0191(9) 0.0017(9) 0.0034(8) -0.0062(9)
C9 0.0185(9) 0.0361(12) 0.0205(9) -0.0008(9) 0.0056(8) -0.0061(9)
C10 0.0265(10) 0.0351(13) 0.0274(10) -0.0039(9) 0.0097(9) -0.0093(9)
C11 0.0226(9) 0.0360(12) 0.0163(9) 0.0022(8) 0.0044(8) -0.0082(9)
C12 0.0274(10) 0.0323(13) 0.0309(10) 0.0035(10) 0.0035(8) 0.0009(9)
C13 0.0297(11) 0.0317(14) 0.0672(17) 0.0002(12) 0.0050(12) 0.0016(10)
Cl2 0.0244(2) 0.0269(3) 0.0264(2) -0.0061(2) 0.00866(18) -0.0007(2)
O5 0.0199(6) 0.0188(7) 0.0235(6) 0.0001(5) 0.0018(5) 0.0008(5)
O6 0.0296(7) 0.0202(8) 0.0264(7) -0.0025(6) 0.0147(6) -0.0049(6)
O7 0.0256(7) 0.0349(9) 0.0152(6) -0.0012(6) 0.0036(5) -0.0118(6)
O8 0.0254(7) 0.0321(8) 0.0147(6) -0.0002(6) 0.0041(5) -0.0091(6)
N5 0.0237(8) 0.0198(9) 0.0218(8) 0.0008(7) 0.0045(6) -0.0012(7)
N6 0.0200(7) 0.0202(9) 0.0195(7) 0.0014(6) 0.0029(6) -0.0031(7)
N7 0.0260(8) 0.0285(10) 0.0267(8) 0.0003(8) 0.0060(7) -0.0058(8)
N8 0.0227(7) 0.0213(9) 0.0167(7) -0.0021(7) 0.0062(6) -0.0065(7)
C14 0.0200(9) 0.0216(10) 0.0199(9) 0.0018(7) 0.0018(7) 0.0048(8)
C15 0.0201(8) 0.0193(10) 0.0209(9) 0.0023(8) 0.0011(7) -0.0026(8)
C16 0.0183(8) 0.0191(9) 0.0162(8) 0.0014(8) 0.0004(7) 0.0001(8)
C17 0.0192(8) 0.0209(10) 0.0171(8) 0.0012(7) 0.0035(7) -0.0009(8)
C18 0.0200(8) 0.0247(11) 0.0161(8) -0.0018(8) 0.0016(7) 0.0018(8)
C19 0.0210(8) 0.0200(10) 0.0181(8) -0.0019(7) 0.0053(7) -0.0025(8)
C20 0.0242(9) 0.0200(10) 0.0167(8) -0.0009(7) 0.0054(7) -0.0004(8)
C21 0.0190(8) 0.0242(11) 0.0161(8) -0.0004(7) 0.0056(7) 0.0002(8)
C22 0.0198(8) 0.0200(10) 0.0207(8) -0.0053(8) 0.0053(7) -0.0009(8)
C23 0.0280(10) 0.0186(10) 0.0255(9) -0.0024(8) 0.0086(8) -0.0032(8)
C24 0.0227(9) 0.0288(11) 0.0155(8) 0.0003(8) 0.0021(7) -0.0047(8)
C25 0.0272(10) 0.0435(14) 0.0206(9) -0.0023(9) 0.0064(8) -0.0011(10)
C26 0.0464(13) 0.0307(13) 0.0291(11) 0.0056(10) 0.0021(10) 0.0023(11)

_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
Cl1 C1 1.7197(19) . ?
O1 C6 1.418(2) . ?
O1 C9 1.438(3) . ?
O2 C10 1.429(2) . ?
O2 H2o 0.8400 . ?
O3 C11 1.424(2) . ?
O3 C8 1.438(2) . ?
O4 C7 1.413(3) . ?
O4 C11 1.424(2) . ?
N1 C1 1.321(3) . ?
N1 C2 1.354(2) . ?
N2 C2 1.323(2) . ?
N2 C3 1.350(3) . ?
N3 C5 1.146(3) . ?
N4 C3 1.339(2) . ?
N4 C6 1.461(2) . ?
N4 H4N 0.83(3) . ?
C1 C4 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(2) . ?
C4 C5 1.427(3) . ?
C6 C7 1.532(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.535(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.520(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.505(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.509(3) . ?
C11 C13 1.510(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
Cl2 C14 1.720(2) . ?
O5 C19 1.404(2) . ?
O5 C22 1.446(2) . ?
O6 C23 1.423(2) . ?
O6 H6o 0.8400 . ?
O7 C21 1.424(2) . ?
O7 C24 1.449(2) . ?
O8 C20 1.419(2) . ?
O8 C24 1.435(2) . ?
N5 C14 1.324(3) . ?
N5 C15 1.345(2) . ?
N6 C15 1.324(3) . ?
N6 C16 1.349(2) . ?
N7 C18 1.154(3) . ?
N8 C16 1.336(3) . ?
N8 C19 1.464(2) . ?
N8 H8N 0.83(2) . ?
C14 C17 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.422(2) . ?
C17 C18 1.428(3) . ?
C19 C20 1.519(3) . ?
C19 H19 1.0000 . ?
C20 C21 1.530(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.534(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.512(3) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.505(3) . ?
C24 C26 1.507(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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 O1 C9 110.69(15) . . ?
C10 O2 H2o 109.5 . . ?
C11 O3 C8 108.03(14) . . ?
C7 O4 C11 110.09(15) . . ?
C1 N1 C2 114.85(16) . . ?
C2 N2 C3 117.19(17) . . ?
C3 N4 C6 122.40(17) . . ?
C3 N4 H4N 120.4(17) . . ?
C6 N4 H4N 115.7(17) . . ?
N1 C1 C4 123.98(17) . . ?
N1 C1 Cl1 116.91(14) . . ?
C4 C1 Cl1 119.11(15) . . ?
N2 C2 N1 127.33(19) . . ?
N2 C2 H2 116.3 . . ?
N1 C2 H2 116.3 . . ?
N4 C3 N2 118.72(17) . . ?
N4 C3 C4 121.39(17) . . ?
N2 C3 C4 119.88(16) . . ?
C1 C4 C3 116.68(17) . . ?
C1 C4 C5 122.83(17) . . ?
C3 C4 C5 120.41(16) . . ?
N3 C5 C4 177.48(19) . . ?
O1 C6 N4 109.17(16) . . ?
O1 C6 C7 107.06(15) . . ?
N4 C6 C7 112.25(16) . . ?
O1 C6 H6 109.4 . . ?
N4 C6 H6 109.4 . . ?
C7 C6 H6 109.4 . . ?
O4 C7 C6 111.1(2) . . ?
O4 C7 C8 105.45(15) . . ?
C6 C7 C8 104.81(15) . . ?
O4 C7 H7 111.7 . . ?
C6 C7 H7 111.7 . . ?
C8 C7 H7 111.7 . . ?
O3 C8 C9 108.39(17) . . ?
O3 C8 C7 103.30(17) . . ?
C9 C8 C7 105.49(15) . . ?
O3 C8 H8 113.0 . . ?
C9 C8 H8 113.0 . . ?
C7 C8 H8 113.0 . . ?
O1 C9 C10 112.16(16) . . ?
O1 C9 C8 104.98(15) . . ?
C10 C9 C8 116.20(19) . . ?
O1 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
O2 C10 C9 110.75(16) . . ?
O2 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O4 C11 O3 105.70(15) . . ?
O4 C11 C12 109.87(17) . . ?
O3 C11 C12 111.86(18) . . ?
O4 C11 C13 108.5(2) . . ?
O3 C11 C13 107.67(17) . . ?
C12 C11 C13 112.94(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 O5 C22 110.36(14) . . ?
C23 O6 H6o 109.5 . . ?
C21 O7 C24 108.86(14) . . ?
C20 O8 C24 107.09(13) . . ?
C14 N5 C15 114.76(17) . . ?
C15 N6 C16 117.00(16) . . ?
C16 N8 C19 122.87(16) . . ?
C16 N8 H8N 122.1(14) . . ?
C19 N8 H8N 114.5(14) . . ?
N5 C14 C17 123.77(18) . . ?
N5 C14 Cl2 117.30(15) . . ?
C17 C14 Cl2 118.92(15) . . ?
N6 C15 N5 127.94(18) . . ?
N6 C15 H15 116.0 . . ?
N5 C15 H15 116.0 . . ?
N8 C16 N6 118.11(16) . . ?
N8 C16 C17 121.91(17) . . ?
N6 C16 C17 119.98(18) . . ?
C14 C17 C16 116.54(17) . . ?
C14 C17 C18 122.60(17) . . ?
C16 C17 C18 120.86(18) . . ?
N7 C18 C17 177.4(2) . . ?
O5 C19 N8 108.87(15) . . ?
O5 C19 C20 106.08(15) . . ?
N8 C19 C20 110.45(15) . . ?
O5 C19 H19 110.4 . . ?
N8 C19 H19 110.4 . . ?
C20 C19 H19 110.4 . . ?
O8 C20 C19 109.22(15) . . ?
O8 C20 C21 102.53(14) . . ?
C19 C20 C21 104.64(16) . . ?
O8 C20 H20 113.2 . . ?
C19 C20 H20 113.2 . . ?
C21 C20 H20 113.2 . . ?
O7 C21 C20 105.13(15) . . ?
O7 C21 C22 112.33(16) . . ?
C20 C21 C22 104.22(15) . . ?
O7 C21 H21 111.6 . . ?
C20 C21 H21 111.6 . . ?
C22 C21 H21 111.6 . . ?
O5 C22 C23 109.88(15) . . ?
O5 C22 C21 106.98(15) . . ?
C23 C22 C21 114.94(15) . . ?
O5 C22 H22 108.3 . . ?
C23 C22 H22 108.3 . . ?
C21 C22 H22 108.3 . . ?
O6 C23 C22 109.77(17) . . ?
O6 C23 H23A 109.7 . . ?
C22 C23 H23A 109.7 . . ?
O6 C23 H23B 109.7 . . ?
C22 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
O8 C24 O7 104.26(14) . . ?
O8 C24 C25 107.76(15) . . ?
O7 C24 C25 109.92(17) . . ?
O8 C24 C26 111.03(17) . . ?
O7 C24 C26 109.52(17) . . ?
C25 C24 C26 113.90(17) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C2 N1 C1 C4 -1.8(3) . . . . ?
C2 N1 C1 Cl1 177.55(14) . . . . ?
C3 N2 C2 N1 1.8(3) . . . . ?
C1 N1 C2 N2 -1.0(3) . . . . ?
C6 N4 C3 N2 6.0(3) . . . . ?
C6 N4 C3 C4 -174.61(17) . . . . ?
C2 N2 C3 N4 179.43(17) . . . . ?
C2 N2 C3 C4 0.1(3) . . . . ?
N1 C1 C4 C3 3.4(3) . . . . ?
Cl1 C1 C4 C3 -175.95(13) . . . . ?
N1 C1 C4 C5 179.98(18) . . . . ?
Cl1 C1 C4 C5 0.7(2) . . . . ?
N4 C3 C4 C1 178.24(17) . . . . ?
N2 C3 C4 C1 -2.4(3) . . . . ?
N4 C3 C4 C5 1.5(3) . . . . ?
N2 C3 C4 C5 -179.09(17) . . . . ?
C1 C4 C5 N3 -179(100) . . . . ?
C3 C4 C5 N3 -2(5) . . . . ?
C9 O1 C6 N4 -100.89(18) . . . . ?
C9 O1 C6 C7 20.8(2) . . . . ?
C3 N4 C6 O1 -144.54(18) . . . . ?
C3 N4 C6 C7 96.9(2) . . . . ?
C11 O4 C7 C6 -114.88(19) . . . . ?
C11 O4 C7 C8 -1.9(2) . . . . ?
O1 C6 C7 O4 108.19(18) . . . . ?
N4 C6 C7 O4 -132.04(17) . . . . ?
O1 C6 C7 C8 -5.2(2) . . . . ?
N4 C6 C7 C8 114.57(18) . . . . ?
C11 O3 C8 C9 137.40(17) . . . . ?
C11 O3 C8 C7 25.8(2) . . . . ?
O4 C7 C8 O3 -14.5(2) . . . . ?
C6 C7 C8 O3 102.84(18) . . . . ?
O4 C7 C8 C9 -128.16(19) . . . . ?
C6 C7 C8 C9 -10.9(2) . . . . ?
C6 O1 C9 C10 99.35(18) . . . . ?
C6 O1 C9 C8 -27.7(2) . . . . ?
O3 C8 C9 O1 -87.19(18) . . . . ?
C7 C8 C9 O1 22.9(2) . . . . ?
O3 C8 C9 C10 148.26(17) . . . . ?
C7 C8 C9 C10 -101.6(2) . . . . ?
O1 C9 C10 O2 -62.0(2) . . . . ?
C8 C9 C10 O2 58.8(2) . . . . ?
C7 O4 C11 O3 17.9(2) . . . . ?
C7 O4 C11 C12 -103.0(2) . . . . ?
C7 O4 C11 C13 133.1(2) . . . . ?
C8 O3 C11 O4 -27.7(2) . . . . ?
C8 O3 C11 C12 91.90(19) . . . . ?
C8 O3 C11 C13 -143.45(18) . . . . ?
C15 N5 C14 C17 -0.3(3) . . . . ?
C15 N5 C14 Cl2 179.10(13) . . . . ?
C16 N6 C15 N5 -0.8(3) . . . . ?
C14 N5 C15 N6 0.8(3) . . . . ?
C19 N8 C16 N6 4.1(3) . . . . ?
C19 N8 C16 C17 -175.61(17) . . . . ?
C15 N6 C16 N8 -179.57(17) . . . . ?
C15 N6 C16 C17 0.2(3) . . . . ?
N5 C14 C17 C16 -0.1(3) . . . . ?
Cl2 C14 C17 C16 -179.56(13) . . . . ?
N5 C14 C17 C18 -179.79(18) . . . . ?
Cl2 C14 C17 C18 0.8(3) . . . . ?
N8 C16 C17 C14 179.96(17) . . . . ?
N6 C16 C17 C14 0.2(3) . . . . ?
N8 C16 C17 C18 -0.4(3) . . . . ?
N6 C16 C17 C18 179.88(17) . . . . ?
C14 C17 C18 N7 173(5) . . . . ?
C16 C17 C18 N7 -7(5) . . . . ?
C22 O5 C19 N8 -92.25(17) . . . . ?
C22 O5 C19 C20 26.61(19) . . . . ?
C16 N8 C19 O5 -159.28(16) . . . . ?
C16 N8 C19 C20 84.6(2) . . . . ?
C24 O8 C20 C19 -145.21(17) . . . . ?
C24 O8 C20 C21 -34.62(19) . . . . ?
O5 C19 C20 O8 81.38(18) . . . . ?
N8 C19 C20 O8 -160.80(15) . . . . ?
O5 C19 C20 C21 -27.79(18) . . . . ?
N8 C19 C20 C21 90.02(18) . . . . ?
C24 O7 C21 C20 -3.2(2) . . . . ?
C24 O7 C21 C22 109.49(18) . . . . ?
O8 C20 C21 O7 22.91(19) . . . . ?
C19 C20 C21 O7 136.90(15) . . . . ?
O8 C20 C21 C22 -95.42(16) . . . . ?
C19 C20 C21 C22 18.57(18) . . . . ?
C19 O5 C22 C23 110.98(17) . . . . ?
C19 O5 C22 C21 -14.43(19) . . . . ?
O7 C21 C22 O5 -116.91(16) . . . . ?
C20 C21 C22 O5 -3.63(18) . . . . ?
O7 C21 C22 C23 120.80(17) . . . . ?
C20 C21 C22 C23 -125.92(17) . . . . ?
O5 C22 C23 O6 -64.4(2) . . . . ?
C21 C22 C23 O6 56.3(2) . . . . ?
C20 O8 C24 O7 33.27(19) . . . . ?
C20 O8 C24 C25 150.05(17) . . . . ?
C20 O8 C24 C26 -84.6(2) . . . . ?
C21 O7 C24 O8 -17.6(2) . . . . ?
C21 O7 C24 C25 -132.84(16) . . . . ?
C21 O7 C24 C26 101.30(18) . . . . ?

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
O2 H2o N5 0.84 2.13 2.963(2) 172.2 1_565
N4 H4N O2 0.83(3) 2.12(3) 2.822(2) 142(2) .
O6 H6o N1 0.84 2.04 2.875(2) 174.6 1_665
N8 H8N O6 0.83(2) 2.08(2) 2.832(2) 149.1(19) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050