# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Ian Hardcastle'
'Johanne Bentley'
'A. Hillary Calvert'
'William Clegg'
'Nicola J. Curtin'
'Jane A. Endicott'
'B. Golding'
'Roger Griffin'
'Karen Haggerty'
'Ross W. Harrington'
'Francesco Marchetti'
'Veronique Mesguiche'
'David R. Newell'
'Martin E. M. Noble'
'Rachel J. Parsons'
'David J. Pratt'
'Kerry Sayle'
'Lan Z. Wang'

_publ_contact_author_name        'Ian Hardcastle'
_publ_contact_author_address     
;
Northern Institute for Cancer Research
Newcastle University
Bedson Building - Chemistry
Newcastle University
Newcastle upon Tyne
NE1 4RW
UNITED KINGDOM
;

_publ_contact_author_email       I.R.HARDCASTLE@NCL.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Structure-Based Design of
2-Arylamino-4-cyclohexylmethoxy-5-
nitroso-6-aminopyrimidine Inhibitors of
Cyclin-Dependent Kinase 2
;

data_rjg37_compound_3a
_database_code_depnum_ccdc_archive 'CCDC 639379'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Cl2 N3 O2'
_chemical_formula_sum            'C20 H19 Cl2 N3 O2'
_chemical_formula_weight         404.28

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'
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/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                   21.9143(10)
_cell_length_b                   10.1032(5)
_cell_length_c                   8.7088(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.099(1)
_cell_angle_gamma                90.00
_cell_volume                     1908.94(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      32.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.8462
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 16.2smx'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker APEX2 CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            13035
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         32.00
_reflns_number_total             3886
_reflns_number_gt                3298
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.0469P)^2^+0.7700P] 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         3886
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cl1 Cl 0.12693(2) 0.79059(4) 0.70303(5) 0.03598(13) Uani 1 1 d . . .
Cl2 Cl 0.31196(2) 0.92749(4) 0.42687(6) 0.04150(14) Uani 1 1 d . . .
O1 O 0.02925(6) 0.09222(14) 0.18698(16) 0.0455(3) Uani 1 1 d . . .
O2 O 0.53369(6) 0.22473(14) 0.67484(16) 0.0437(3) Uani 1 1 d . . .
N1 N 0.22168(6) 0.84447(13) 0.56435(16) 0.0300(3) Uani 1 1 d . . .
N2 N 0.28214(6) 0.68033(14) 0.45479(16) 0.0297(3) Uani 1 1 d . . .
N3 N 0.26162(6) 0.45620(13) 0.47373(15) 0.0256(3) Uani 1 1 d . . .
C1 C 0.18847(8) 0.74399(17) 0.60966(18) 0.0280(3) Uani 1 1 d . . .
C2 C 0.19836(7) 0.61316(16) 0.58704(17) 0.0250(3) Uani 1 1 d . . .
H2B H 0.1735 0.5466 0.6242 0.030 Uiso 1 1 calc R . .
C3 C 0.24741(7) 0.58177(15) 0.50553(17) 0.0249(3) Uani 1 1 d . . .
C4 C 0.26631(8) 0.80218(16) 0.48881(19) 0.0300(4) Uani 1 1 d . . .
C5 C 0.23431(8) 0.34233(16) 0.54187(19) 0.0293(4) Uani 1 1 d . . .
H5A H 0.2202 0.3706 0.6398 0.035 Uiso 1 1 calc R . .
H5B H 0.2667 0.2744 0.5681 0.035 Uiso 1 1 calc R . .
C6 C 0.18062(7) 0.27972(15) 0.43906(18) 0.0264(3) Uani 1 1 d . . .
C7 C 0.13978(8) 0.35295(17) 0.3355(2) 0.0315(4) Uani 1 1 d . . .
H7A H 0.1468 0.4450 0.3243 0.038 Uiso 1 1 calc R . .
C8 C 0.08893(8) 0.29431(17) 0.2482(2) 0.0332(4) Uani 1 1 d . . .
H8A H 0.0616 0.3458 0.1778 0.040 Uiso 1 1 calc R . .
C9 C 0.07843(8) 0.16024(18) 0.2645(2) 0.0328(4) Uani 1 1 d . . .
C10 C 0.11929(8) 0.08532(17) 0.3662(2) 0.0340(4) Uani 1 1 d . . .
H10A H 0.1124 -0.0069 0.3768 0.041 Uiso 1 1 calc R . .
C11 C 0.16981(8) 0.14461(16) 0.45187(19) 0.0298(4) Uani 1 1 d . . .
H11A H 0.1976 0.0925 0.5205 0.036 Uiso 1 1 calc R . .
C12 C -0.01074(9) 0.1634(2) 0.0720(2) 0.0472(5) Uani 1 1 d . . .
H12A H -0.0441 0.1051 0.0260 0.071 Uiso 1 1 calc R . .
H12B H 0.0127 0.1943 -0.0090 0.071 Uiso 1 1 calc R . .
H12C H -0.0282 0.2396 0.1202 0.071 Uiso 1 1 calc R . .
C13 C 0.30655(7) 0.42387(16) 0.36862(19) 0.0284(4) Uani 1 1 d . . .
H13A H 0.3145 0.5040 0.3091 0.034 Uiso 1 1 calc R . .
H13B H 0.2886 0.3558 0.2937 0.034 Uiso 1 1 calc R . .
C14 C 0.36679(7) 0.37347(16) 0.45302(18) 0.0265(3) Uani 1 1 d . . .
C15 C 0.38614(8) 0.24473(17) 0.4309(2) 0.0333(4) Uani 1 1 d . . .
H15A H 0.3610 0.1880 0.3616 0.040 Uiso 1 1 calc R . .
C16 C 0.44141(8) 0.19774(18) 0.5079(2) 0.0386(4) Uani 1 1 d . . .
H16A H 0.4536 0.1090 0.4925 0.046 Uiso 1 1 calc R . .
C17 C 0.47913(8) 0.28010(18) 0.6078(2) 0.0325(4) Uani 1 1 d . . .
C18 C 0.46069(8) 0.40883(17) 0.6317(2) 0.0336(4) Uani 1 1 d . . .
H18A H 0.4861 0.4657 0.7001 0.040 Uiso 1 1 calc R . .
C19 C 0.40477(8) 0.45377(17) 0.5549(2) 0.0332(4) Uani 1 1 d . . .
H19A H 0.3921 0.5418 0.5725 0.040 Uiso 1 1 calc R . .
C20 C 0.57485(9) 0.3074(2) 0.7745(2) 0.0446(5) Uani 1 1 d . . .
H20A H 0.6146 0.2624 0.8007 0.067 Uiso 1 1 calc R . .
H20B H 0.5572 0.3256 0.8697 0.067 Uiso 1 1 calc R . .
H20C H 0.5810 0.3909 0.7215 0.067 Uiso 1 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 0.0411(3) 0.0305(2) 0.0365(2) -0.00751(17) 0.00616(18) 0.00235(17)
Cl2 0.0365(3) 0.0337(3) 0.0518(3) 0.00807(19) -0.0023(2) -0.00870(18)
O1 0.0455(8) 0.0479(8) 0.0409(8) -0.0032(6) -0.0017(6) -0.0172(6)
O2 0.0319(7) 0.0479(8) 0.0485(8) 0.0046(6) -0.0039(6) 0.0078(6)
N1 0.0330(8) 0.0237(7) 0.0305(8) -0.0013(6) -0.0055(6) -0.0021(6)
N2 0.0285(7) 0.0283(7) 0.0296(7) 0.0030(6) -0.0049(6) -0.0014(6)
N3 0.0288(7) 0.0218(7) 0.0257(7) 0.0026(5) 0.0019(5) -0.0005(5)
C1 0.0318(8) 0.0272(8) 0.0225(8) -0.0028(6) -0.0048(6) 0.0005(7)
C2 0.0297(8) 0.0231(8) 0.0202(7) 0.0000(6) -0.0032(6) -0.0017(6)
C3 0.0262(8) 0.0255(8) 0.0207(8) 0.0012(6) -0.0054(6) -0.0012(6)
C4 0.0299(9) 0.0274(9) 0.0290(9) 0.0022(7) -0.0081(7) -0.0035(7)
C5 0.0344(9) 0.0236(8) 0.0289(9) 0.0074(7) 0.0007(7) -0.0001(7)
C6 0.0307(8) 0.0238(8) 0.0255(8) 0.0029(6) 0.0064(7) 0.0008(6)
C7 0.0349(9) 0.0245(8) 0.0338(9) 0.0059(7) 0.0009(7) -0.0015(7)
C8 0.0328(9) 0.0358(10) 0.0301(9) 0.0059(7) 0.0007(7) -0.0003(7)
C9 0.0341(9) 0.0374(10) 0.0278(9) -0.0048(7) 0.0068(7) -0.0082(7)
C10 0.0456(10) 0.0241(9) 0.0336(9) -0.0020(7) 0.0096(8) -0.0052(7)
C11 0.0374(9) 0.0248(8) 0.0277(8) 0.0023(6) 0.0063(7) 0.0027(7)
C12 0.0359(10) 0.0650(14) 0.0396(11) -0.0057(10) 0.0012(8) -0.0091(9)
C13 0.0322(9) 0.0273(9) 0.0249(8) -0.0017(6) 0.0011(7) 0.0013(7)
C14 0.0288(8) 0.0264(8) 0.0243(8) 0.0030(6) 0.0035(6) 0.0006(6)
C15 0.0317(9) 0.0289(9) 0.0381(10) -0.0051(7) 0.0006(7) -0.0013(7)
C16 0.0382(10) 0.0291(9) 0.0477(11) -0.0025(8) 0.0033(8) 0.0071(8)
C17 0.0276(9) 0.0378(10) 0.0321(9) 0.0089(7) 0.0040(7) 0.0028(7)
C18 0.0347(9) 0.0314(9) 0.0320(9) 0.0028(7) -0.0045(7) -0.0034(7)
C19 0.0381(10) 0.0259(9) 0.0334(9) -0.0004(7) -0.0026(7) 0.0022(7)
C20 0.0319(10) 0.0529(12) 0.0460(11) 0.0138(9) -0.0044(8) -0.0019(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
Cl1 C1 1.7350(17) . ?
Cl2 C4 1.7455(17) . ?
O1 C9 1.373(2) . ?
O1 C12 1.428(2) . ?
O2 C17 1.374(2) . ?
O2 C20 1.430(2) . ?
N1 C1 1.340(2) . ?
N1 C4 1.324(2) . ?
N2 C3 1.364(2) . ?
N2 C4 1.324(2) . ?
N3 C3 1.344(2) . ?
N3 C5 1.461(2) . ?
N3 C13 1.472(2) . ?
C1 C2 1.358(2) . ?
C2 H2B 0.950 . ?
C2 C3 1.405(2) . ?
C5 H5A 0.990 . ?
C5 H5B 0.990 . ?
C5 C6 1.513(2) . ?
C6 C7 1.391(2) . ?
C6 C11 1.393(2) . ?
C7 H7A 0.950 . ?
C7 C8 1.390(2) . ?
C8 H8A 0.950 . ?
C8 C9 1.385(2) . ?
C9 C10 1.391(3) . ?
C10 H10A 0.950 . ?
C10 C11 1.381(2) . ?
C11 H11A 0.950 . ?
C12 H12A 0.980 . ?
C12 H12B 0.980 . ?
C12 H12C 0.980 . ?
C13 H13A 0.990 . ?
C13 H13B 0.990 . ?
C13 C14 1.506(2) . ?
C14 C15 1.390(2) . ?
C14 C19 1.389(2) . ?
C15 H15A 0.950 . ?
C15 C16 1.383(2) . ?
C16 H16A 0.950 . ?
C16 C17 1.389(3) . ?
C17 C18 1.386(3) . ?
C18 H18A 0.950 . ?
C18 C19 1.387(2) . ?
C19 H19A 0.950 . ?
C20 H20A 0.980 . ?
C20 H20B 0.980 . ?
C20 H20C 0.980 . ?

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
C9 O1 C12 117.03(15) . . ?
C17 O2 C20 117.19(15) . . ?
C1 N1 C4 111.81(14) . . ?
C3 N2 C4 115.50(14) . . ?
C3 N3 C5 122.65(14) . . ?
C3 N3 C13 122.14(13) . . ?
C5 N3 C13 115.21(13) . . ?
Cl1 C1 N1 115.00(12) . . ?
Cl1 C1 C2 118.85(13) . . ?
N1 C1 C2 126.15(16) . . ?
C1 C2 H2B 121.9 . . ?
C1 C2 C3 116.23(15) . . ?
H2B C2 C3 121.9 . . ?
N2 C3 N3 117.78(14) . . ?
N2 C3 C2 120.02(14) . . ?
N3 C3 C2 122.20(14) . . ?
Cl2 C4 N1 114.53(12) . . ?
Cl2 C4 N2 115.19(13) . . ?
N1 C4 N2 130.28(16) . . ?
N3 C5 H5A 108.6 . . ?
N3 C5 H5B 108.6 . . ?
N3 C5 C6 114.70(13) . . ?
H5A C5 H5B 107.6 . . ?
H5A C5 C6 108.6 . . ?
H5B C5 C6 108.6 . . ?
C5 C6 C7 122.48(14) . . ?
C5 C6 C11 119.29(14) . . ?
C7 C6 C11 118.18(15) . . ?
C6 C7 H7A 119.3 . . ?
C6 C7 C8 121.40(16) . . ?
H7A C7 C8 119.3 . . ?
C7 C8 H8A 120.2 . . ?
C7 C8 C9 119.51(16) . . ?
H8A C8 C9 120.2 . . ?
O1 C9 C8 124.70(17) . . ?
O1 C9 C10 115.53(16) . . ?
C8 C9 C10 119.77(16) . . ?
C9 C10 H10A 119.9 . . ?
C9 C10 C11 120.18(16) . . ?
H10A C10 C11 119.9 . . ?
C6 C11 C10 120.95(16) . . ?
C6 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
N3 C13 C14 112.86(13) . . ?
H13A C13 H13B 107.8 . . ?
H13A C13 C14 109.0 . . ?
H13B C13 C14 109.0 . . ?
C13 C14 C15 120.81(15) . . ?
C13 C14 C19 121.28(15) . . ?
C15 C14 C19 117.91(15) . . ?
C14 C15 H15A 119.4 . . ?
C14 C15 C16 121.15(16) . . ?
H15A C15 C16 119.4 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 C17 120.07(16) . . ?
H16A C16 C17 120.0 . . ?
O2 C17 C16 115.32(16) . . ?
O2 C17 C18 124.94(16) . . ?
C16 C17 C18 119.73(16) . . ?
C17 C18 H18A 120.3 . . ?
C17 C18 C19 119.40(16) . . ?
H18A C18 C19 120.3 . . ?
C14 C19 C18 121.72(16) . . ?
C14 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N1 C1 Cl1 -177.56(11) . . . . ?
C4 N1 C1 C2 1.5(2) . . . . ?
Cl1 C1 C2 C3 177.63(11) . . . . ?
N1 C1 C2 C3 -1.4(2) . . . . ?
C5 N3 C3 N2 170.27(13) . . . . ?
C5 N3 C3 C2 -10.2(2) . . . . ?
C13 N3 C3 N2 -9.0(2) . . . . ?
C13 N3 C3 C2 170.49(14) . . . . ?
C4 N2 C3 N3 179.93(14) . . . . ?
C4 N2 C3 C2 0.4(2) . . . . ?
C1 C2 C3 N2 0.3(2) . . . . ?
C1 C2 C3 N3 -179.18(14) . . . . ?
C3 N2 C4 Cl2 178.76(11) . . . . ?
C3 N2 C4 N1 -0.3(3) . . . . ?
C1 N1 C4 Cl2 -179.66(11) . . . . ?
C1 N1 C4 N2 -0.6(2) . . . . ?
C3 N3 C5 C6 98.09(18) . . . . ?
C13 N3 C5 C6 -82.58(17) . . . . ?
N3 C5 C6 C7 -32.9(2) . . . . ?
N3 C5 C6 C11 149.70(15) . . . . ?
C5 C6 C7 C8 -176.58(16) . . . . ?
C11 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C12 O1 C9 C8 5.5(3) . . . . ?
C12 O1 C9 C10 -174.82(16) . . . . ?
C7 C8 C9 O1 178.66(16) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
O1 C9 C10 C11 -178.98(15) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C5 C6 C11 C10 176.37(15) . . . . ?
C7 C6 C11 C10 -1.2(2) . . . . ?
C3 N3 C13 C14 106.71(17) . . . . ?
C5 N3 C13 C14 -72.63(17) . . . . ?
N3 C13 C14 C15 115.33(17) . . . . ?
N3 C13 C14 C19 -64.8(2) . . . . ?
C13 C14 C15 C16 179.97(17) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C20 O2 C17 C16 178.01(16) . . . . ?
C20 O2 C17 C18 -1.2(3) . . . . ?
C15 C16 C17 O2 -178.23(16) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
O2 C17 C18 C19 178.94(16) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C13 C14 C19 C18 -179.17(16) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.043

#===END

data_rjg36_compound_4a
_database_code_depnum_ccdc_archive 'CCDC 639380'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 Cl N4 O3'
_chemical_formula_sum            'C27 H27 Cl N4 O3'
_chemical_formula_weight         490.98

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   'C 2/c'

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

_cell_length_a                   16.9620(14)
_cell_length_b                   10.7877(9)
_cell_length_c                   27.228(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.375(1)
_cell_angle_gamma                90.00
_cell_volume                     4929.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4209
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      32.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.8462
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 16.2smx'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker APEX2 CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        5
_diffrn_reflns_number            15124
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         32.00
_reflns_number_total             5026
_reflns_number_gt                4256
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.0578P)^2^+2.0037P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5026
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Cl1 Cl 0.09740(2) 0.66413(4) 0.145809(14) 0.02608(13) Uani 1 1 d . . .
O1 O 0.12047(7) 0.22738(11) 0.48910(4) 0.0281(3) Uani 1 1 d . . .
O2 O 0.29586(8) 0.88783(12) 0.46835(5) 0.0360(3) Uani 1 1 d . . .
O3 O 0.41518(8) 0.28997(10) 0.07987(4) 0.0294(3) Uani 1 1 d . . .
N1 N 0.09227(8) 0.55012(11) 0.22966(5) 0.0182(3) Uani 1 1 d . . .
N2 N 0.20690(7) 0.50353(12) 0.28973(5) 0.0174(3) Uani 1 1 d . . .
N3 N 0.07727(8) 0.45896(12) 0.30321(5) 0.0190(3) Uani 1 1 d . . .
H3 H 0.0283(13) 0.4783(17) 0.2931(7) 0.030(5) Uiso 1 1 d . . .
N4 N 0.33388(8) 0.55334(13) 0.27687(5) 0.0224(3) Uani 1 1 d . . .
C1 C 0.12899(9) 0.50481(13) 0.27377(5) 0.0161(3) Uani 1 1 d . . .
C2 C 0.14207(9) 0.59885(14) 0.20174(6) 0.0181(3) Uani 1 1 d . . .
C3 C 0.22350(9) 0.60383(14) 0.21284(6) 0.0198(3) Uani 1 1 d . . .
H3B H 0.2562 0.6389 0.1909 0.024 Uiso 1 1 calc R . .
C4 C 0.25503(9) 0.55279(14) 0.25939(6) 0.0183(3) Uani 1 1 d . . .
C5 C 0.09203(9) 0.40034(13) 0.35019(6) 0.0174(3) Uani 1 1 d . . .
C6 C 0.02516(9) 0.36962(14) 0.37182(6) 0.0195(3) Uani 1 1 d . . .
H6A H -0.0263 0.3882 0.3546 0.023 Uiso 1 1 calc R . .
C7 C 0.03158(10) 0.31257(14) 0.41800(6) 0.0212(3) Uani 1 1 d . . .
H7A H -0.0149 0.2929 0.4322 0.025 Uiso 1 1 calc R . .
C8 C 0.10687(10) 0.28449(14) 0.44328(6) 0.0209(3) Uani 1 1 d . . .
C9 C 0.17401(10) 0.31368(15) 0.42196(6) 0.0229(4) Uani 1 1 d . . .
H9A H 0.2253 0.2939 0.4391 0.028 Uiso 1 1 calc R . .
C10 C 0.16732(10) 0.37139(15) 0.37591(6) 0.0222(3) Uani 1 1 d . . .
H10A H 0.2139 0.3912 0.3619 0.027 Uiso 1 1 calc R . .
C11 C 0.05330(12) 0.21362(18) 0.51474(7) 0.0342(4) Uani 1 1 d . . .
H11A H 0.0708 0.1797 0.5479 0.051 Uiso 1 1 calc R . .
H11B H 0.0147 0.1570 0.4962 0.051 Uiso 1 1 calc R . .
H11C H 0.0283 0.2946 0.5177 0.051 Uiso 1 1 calc R . .
C12 C 0.36080(10) 0.52201(16) 0.32898(6) 0.0230(4) Uani 1 1 d . . .
H12A H 0.4190 0.5069 0.3336 0.028 Uiso 1 1 calc R . .
H12B H 0.3345 0.4442 0.3371 0.028 Uiso 1 1 calc R . .
C13 C 0.34289(9) 0.62272(15) 0.36464(6) 0.0204(3) Uani 1 1 d . . .
C14 C 0.32327(10) 0.74298(15) 0.34943(6) 0.0231(4) Uani 1 1 d . . .
H14A H 0.3205 0.7633 0.3153 0.028 Uiso 1 1 calc R . .
C15 C 0.30742(10) 0.83499(15) 0.38258(6) 0.0238(4) Uani 1 1 d . . .
H15A H 0.2943 0.9167 0.3711 0.029 Uiso 1 1 calc R . .
C16 C 0.31098(10) 0.80584(16) 0.43246(6) 0.0248(4) Uani 1 1 d . . .
C17 C 0.33027(11) 0.68528(16) 0.44877(6) 0.0286(4) Uani 1 1 d . . .
H17A H 0.3330 0.6650 0.4829 0.034 Uiso 1 1 calc R . .
C18 C 0.34538(10) 0.59582(16) 0.41517(6) 0.0256(4) Uani 1 1 d . . .
H18A H 0.3578 0.5139 0.4266 0.031 Uiso 1 1 calc R . .
C19 C 0.28095(13) 1.01341(18) 0.45405(7) 0.0404(5) Uani 1 1 d . . .
H19A H 0.2715 1.0621 0.4830 0.061 Uiso 1 1 calc R . .
H19B H 0.2339 1.0177 0.4286 0.061 Uiso 1 1 calc R . .
H19C H 0.3272 1.0470 0.4407 0.061 Uiso 1 1 calc R . .
C20 C 0.39143(10) 0.59891(16) 0.24602(6) 0.0236(4) Uani 1 1 d . . .
H20A H 0.4439 0.6089 0.2669 0.028 Uiso 1 1 calc R . .
H20B H 0.3742 0.6815 0.2327 0.028 Uiso 1 1 calc R . .
C21 C 0.40047(9) 0.51265(15) 0.20300(6) 0.0200(3) Uani 1 1 d . . .
C22 C 0.39608(11) 0.38494(16) 0.20761(6) 0.0294(4) Uani 1 1 d . . .
H22A H 0.3892 0.3501 0.2387 0.035 Uiso 1 1 calc R . .
C23 C 0.40157(11) 0.30685(15) 0.16762(7) 0.0290(4) Uani 1 1 d . . .
H23A H 0.3979 0.2196 0.1714 0.035 Uiso 1 1 calc R . .
C24 C 0.41248(10) 0.35708(15) 0.12190(6) 0.0215(3) Uani 1 1 d . . .
C25 C 0.42005(10) 0.48447(15) 0.11759(6) 0.0240(4) Uani 1 1 d . . .
H25A H 0.4298 0.5194 0.0870 0.029 Uiso 1 1 calc R . .
C26 C 0.41351(10) 0.56084(15) 0.15761(6) 0.0230(4) Uani 1 1 d . . .
H26A H 0.4180 0.6480 0.1539 0.028 Uiso 1 1 calc R . .
C27 C 0.39308(12) 0.16161(15) 0.08114(7) 0.0320(4) Uani 1 1 d . . .
H27A H 0.3881 0.1269 0.0476 0.048 Uiso 1 1 calc R . .
H27B H 0.3420 0.1543 0.0937 0.048 Uiso 1 1 calc R . .
H27C H 0.4341 0.1161 0.1031 0.048 Uiso 1 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 0.0218(2) 0.0341(2) 0.0214(2) 0.00666(16) -0.00004(17) -0.00034(16)
O1 0.0281(7) 0.0365(7) 0.0206(6) 0.0061(5) 0.0060(5) 0.0018(5)
O2 0.0449(8) 0.0391(7) 0.0255(7) -0.0059(5) 0.0096(6) -0.0027(6)
O3 0.0402(8) 0.0232(6) 0.0255(6) -0.0005(5) 0.0070(6) 0.0014(5)
N1 0.0128(6) 0.0237(7) 0.0184(6) -0.0014(5) 0.0030(5) -0.0009(5)
N2 0.0111(6) 0.0235(6) 0.0181(6) -0.0032(5) 0.0041(5) -0.0007(5)
N3 0.0085(7) 0.0284(7) 0.0199(7) 0.0030(5) 0.0018(5) -0.0003(5)
N4 0.0116(7) 0.0370(8) 0.0187(7) -0.0007(6) 0.0032(5) -0.0021(6)
C1 0.0116(7) 0.0184(7) 0.0186(7) -0.0052(6) 0.0028(6) -0.0002(6)
C2 0.0170(8) 0.0207(7) 0.0164(7) -0.0018(6) 0.0016(6) 0.0005(6)
C3 0.0162(8) 0.0249(8) 0.0195(8) -0.0021(6) 0.0064(6) -0.0035(6)
C4 0.0124(8) 0.0227(8) 0.0208(8) -0.0060(6) 0.0061(6) -0.0007(6)
C5 0.0151(8) 0.0187(7) 0.0187(8) -0.0025(6) 0.0033(6) -0.0011(6)
C6 0.0135(8) 0.0210(7) 0.0244(8) -0.0009(6) 0.0043(6) 0.0008(6)
C7 0.0186(8) 0.0222(8) 0.0244(8) -0.0012(6) 0.0090(7) -0.0013(6)
C8 0.0242(9) 0.0211(8) 0.0177(8) -0.0012(6) 0.0033(7) -0.0009(6)
C9 0.0170(8) 0.0285(8) 0.0223(8) -0.0005(7) -0.0005(7) 0.0010(7)
C10 0.0144(8) 0.0299(8) 0.0227(8) -0.0001(7) 0.0044(6) -0.0027(7)
C11 0.0359(11) 0.0437(11) 0.0255(9) 0.0092(8) 0.0127(8) 0.0015(9)
C12 0.0120(8) 0.0342(9) 0.0220(8) 0.0020(7) 0.0002(6) 0.0004(7)
C13 0.0102(7) 0.0317(9) 0.0188(8) 0.0015(6) 0.0004(6) -0.0038(6)
C14 0.0179(8) 0.0348(9) 0.0161(8) 0.0025(7) 0.0012(6) -0.0046(7)
C15 0.0203(9) 0.0271(8) 0.0234(8) 0.0017(7) 0.0010(7) -0.0041(7)
C16 0.0195(9) 0.0345(9) 0.0207(8) -0.0029(7) 0.0040(7) -0.0062(7)
C17 0.0295(10) 0.0397(10) 0.0164(8) 0.0041(7) 0.0025(7) -0.0056(8)
C18 0.0238(9) 0.0307(9) 0.0221(8) 0.0070(7) 0.0028(7) -0.0016(7)
C19 0.0460(13) 0.0376(10) 0.0360(11) -0.0097(8) 0.0002(9) 0.0022(9)
C20 0.0116(8) 0.0351(9) 0.0250(9) -0.0022(7) 0.0057(7) -0.0045(7)
C21 0.0093(7) 0.0285(8) 0.0226(8) 0.0010(6) 0.0040(6) 0.0014(6)
C22 0.0346(11) 0.0315(9) 0.0254(9) 0.0073(7) 0.0157(8) 0.0051(8)
C23 0.0341(11) 0.0212(8) 0.0349(10) 0.0079(7) 0.0155(8) 0.0033(7)
C24 0.0181(8) 0.0243(8) 0.0224(8) 0.0005(6) 0.0040(7) 0.0040(6)
C25 0.0273(9) 0.0246(8) 0.0207(8) 0.0061(6) 0.0058(7) 0.0007(7)
C26 0.0219(9) 0.0221(8) 0.0250(8) 0.0037(6) 0.0039(7) -0.0012(6)
C27 0.0303(10) 0.0239(9) 0.0403(11) -0.0035(7) -0.0005(9) 0.0004(7)

_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 C2 1.7473(15) . ?
O1 C8 1.3802(19) . ?
O1 C11 1.428(2) . ?
O2 C16 1.369(2) . ?
O2 C19 1.422(2) . ?
O3 C24 1.361(2) . ?
O3 C27 1.436(2) . ?
N1 C1 1.3607(19) . ?
N1 C2 1.325(2) . ?
N2 C1 1.3296(19) . ?
N2 C4 1.352(2) . ?
N3 H3 0.86(2) . ?
N3 C1 1.364(2) . ?
N3 C5 1.4163(19) . ?
N4 C4 1.353(2) . ?
N4 C12 1.465(2) . ?
N4 C20 1.463(2) . ?
C2 C3 1.371(2) . ?
C3 H3B 0.950 . ?
C3 C4 1.414(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.399(2) . ?
C6 H6A 0.950 . ?
C6 C7 1.390(2) . ?
C7 H7A 0.950 . ?
C7 C8 1.393(2) . ?
C8 C9 1.388(2) . ?
C9 H9A 0.950 . ?
C9 C10 1.389(2) . ?
C10 H10A 0.950 . ?
C11 H11A 0.980 . ?
C11 H11B 0.980 . ?
C11 H11C 0.980 . ?
C12 H12A 0.990 . ?
C12 H12B 0.990 . ?
C12 C13 1.517(2) . ?
C13 C14 1.387(2) . ?
C13 C18 1.401(2) . ?
C14 H14A 0.950 . ?
C14 C15 1.394(2) . ?
C15 H15A 0.950 . ?
C15 C16 1.387(2) . ?
C16 C17 1.398(2) . ?
C17 H17A 0.950 . ?
C17 C18 1.379(2) . ?
C18 H18A 0.950 . ?
C19 H19A 0.980 . ?
C19 H19B 0.980 . ?
C19 H19C 0.980 . ?
C20 H20A 0.990 . ?
C20 H20B 0.990 . ?
C20 C21 1.521(2) . ?
C21 C22 1.386(2) . ?
C21 C26 1.388(2) . ?
C22 H22A 0.950 . ?
C22 C23 1.391(2) . ?
C23 H23A 0.950 . ?
C23 C24 1.395(2) . ?
C24 C25 1.387(2) . ?
C25 H25A 0.950 . ?
C25 C26 1.383(2) . ?
C26 H26A 0.950 . ?
C27 H27A 0.980 . ?
C27 H27B 0.980 . ?
C27 H27C 0.980 . ?

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
C8 O1 C11 116.62(13) . . ?
C16 O2 C19 117.67(14) . . ?
C24 O3 C27 116.86(14) . . ?
C1 N1 C2 113.63(13) . . ?
C1 N2 C4 117.14(13) . . ?
H3 N3 C1 113.3(13) . . ?
H3 N3 C5 115.6(13) . . ?
C1 N3 C5 130.41(14) . . ?
C4 N4 C12 119.51(13) . . ?
C4 N4 C20 120.51(13) . . ?
C12 N4 C20 119.58(12) . . ?
N1 C1 N2 126.69(14) . . ?
N1 C1 N3 113.45(13) . . ?
N2 C1 N3 119.85(14) . . ?
Cl1 C2 N1 115.36(12) . . ?
Cl1 C2 C3 118.11(12) . . ?
N1 C2 C3 126.53(14) . . ?
C2 C3 H3B 122.6 . . ?
C2 C3 C4 114.81(14) . . ?
H3B C3 C4 122.6 . . ?
N2 C4 N4 116.15(14) . . ?
N2 C4 C3 121.18(14) . . ?
N4 C4 C3 122.64(14) . . ?
N3 C5 C6 116.15(13) . . ?
N3 C5 C10 125.45(14) . . ?
C6 C5 C10 118.40(14) . . ?
C5 C6 H6A 119.1 . . ?
C5 C6 C7 121.79(14) . . ?
H6A C6 C7 119.1 . . ?
C6 C7 H7A 120.4 . . ?
C6 C7 C8 119.26(15) . . ?
H7A C7 C8 120.4 . . ?
O1 C8 C7 124.35(15) . . ?
O1 C8 C9 116.11(14) . . ?
C7 C8 C9 119.54(15) . . ?
C8 C9 H9A 119.5 . . ?
C8 C9 C10 121.00(15) . . ?
H9A C9 C10 119.5 . . ?
C5 C10 C9 120.00(15) . . ?
C5 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.0 . . ?
N4 C12 H12B 109.0 . . ?
N4 C12 C13 113.04(13) . . ?
H12A C12 H12B 107.8 . . ?
H12A C12 C13 109.0 . . ?
H12B C12 C13 109.0 . . ?
C12 C13 C14 122.71(14) . . ?
C12 C13 C18 120.01(15) . . ?
C14 C13 C18 117.29(15) . . ?
C13 C14 H14A 118.9 . . ?
C13 C14 C15 122.22(15) . . ?
H14A C14 C15 118.9 . . ?
C14 C15 H15A 120.4 . . ?
C14 C15 C16 119.19(15) . . ?
H15A C15 C16 120.4 . . ?
O2 C16 C15 124.49(16) . . ?
O2 C16 C17 115.71(15) . . ?
C15 C16 C17 119.79(16) . . ?
C16 C17 H17A 120.1 . . ?
C16 C17 C18 119.86(15) . . ?
H17A C17 C18 120.1 . . ?
C13 C18 C17 121.64(16) . . ?
C13 C18 H18A 119.2 . . ?
C17 C18 H18A 119.2 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.0 . . ?
N4 C20 H20B 109.0 . . ?
N4 C20 C21 112.78(13) . . ?
H20A C20 H20B 107.8 . . ?
H20A C20 C21 109.0 . . ?
H20B C20 C21 109.0 . . ?
C20 C21 C22 121.70(15) . . ?
C20 C21 C26 120.24(15) . . ?
C22 C21 C26 118.06(15) . . ?
C21 C22 H22A 119.3 . . ?
C21 C22 C23 121.37(16) . . ?
H22A C22 C23 119.3 . . ?
C22 C23 H23A 120.1 . . ?
C22 C23 C24 119.76(15) . . ?
H23A C23 C24 120.1 . . ?
O3 C24 C23 124.69(15) . . ?
O3 C24 C25 116.18(14) . . ?
C23 C24 C25 119.12(15) . . ?
C24 C25 H25A 119.9 . . ?
C24 C25 C26 120.30(15) . . ?
H25A C25 C26 119.9 . . ?
C21 C26 C25 121.32(15) . . ?
C21 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C4 N2 C1 N1 0.4(2) . . . . ?
C4 N2 C1 N3 -178.53(13) . . . . ?
C2 N1 C1 N2 -1.4(2) . . . . ?
C2 N1 C1 N3 177.66(13) . . . . ?
C5 N3 C1 N1 177.23(14) . . . . ?
C5 N3 C1 N2 -3.7(2) . . . . ?
C1 N1 C2 Cl1 -177.45(10) . . . . ?
C1 N1 C2 C3 1.7(2) . . . . ?
Cl1 C2 C3 C4 178.02(11) . . . . ?
N1 C2 C3 C4 -1.1(2) . . . . ?
C1 N2 C4 N4 178.40(13) . . . . ?
C1 N2 C4 C3 0.3(2) . . . . ?
C12 N4 C4 N2 -10.3(2) . . . . ?
C12 N4 C4 C3 167.78(14) . . . . ?
C20 N4 C4 N2 176.97(13) . . . . ?
C20 N4 C4 C3 -4.9(2) . . . . ?
C2 C3 C4 N2 0.0(2) . . . . ?
C2 C3 C4 N4 -177.97(14) . . . . ?
C1 N3 C5 C6 176.79(15) . . . . ?
C1 N3 C5 C10 -3.3(3) . . . . ?
N3 C5 C6 C7 -179.55(14) . . . . ?
C10 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C11 O1 C8 C7 -9.6(2) . . . . ?
C11 O1 C8 C9 170.94(14) . . . . ?
C6 C7 C8 O1 -179.60(14) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
O1 C8 C9 C10 -179.97(14) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
N3 C5 C10 C9 179.96(14) . . . . ?
C6 C5 C10 C9 -0.2(2) . . . . ?
C4 N4 C12 C13 -72.25(18) . . . . ?
C20 N4 C12 C13 100.54(17) . . . . ?
N4 C12 C13 C14 -16.2(2) . . . . ?
N4 C12 C13 C18 163.41(14) . . . . ?
C12 C13 C14 C15 -179.59(15) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C19 O2 C16 C15 -4.6(3) . . . . ?
C19 O2 C16 C17 176.10(16) . . . . ?
C14 C15 C16 O2 -179.31(15) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
O2 C16 C17 C18 179.11(16) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C12 C13 C18 C17 179.31(15) . . . . ?
C14 C13 C18 C17 -1.0(2) . . . . ?
C4 N4 C20 C21 -70.51(19) . . . . ?
C12 N4 C20 C21 116.77(15) . . . . ?
N4 C20 C21 C22 -35.5(2) . . . . ?
N4 C20 C21 C26 144.52(15) . . . . ?
C20 C21 C22 C23 177.69(16) . . . . ?
C26 C21 C22 C23 -2.3(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C27 O3 C24 C23 10.0(2) . . . . ?
C27 O3 C24 C25 -168.96(15) . . . . ?
C22 C23 C24 O3 -177.01(16) . . . . ?
C22 C23 C24 C25 1.9(3) . . . . ?
O3 C24 C25 C26 176.34(15) . . . . ?
C23 C24 C25 C26 -2.7(3) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?
C20 C21 C26 C25 -178.45(15) . . . . ?
C22 C21 C26 C25 1.6(2) . . . . ?

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
N3 H3 N1 0.86(2) 2.19(2) 3.0476(19) 173.1(17) 2

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.057

#===END