# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global
_journal_name_full               Org.Biomol.Chem.
#==============================================================================

# SUBMISSION DETAILS

_journal_coden_Cambridge         0177

_publ_contact_author_name        'David E. Hibbs'
_publ_contact_author_address     
;
David E. Hibbs
Faculty of Pharmacy
University of Sydney
;

_publ_contact_author_email       davidh@pharm.usyd.edu.au
_publ_contact_author_fax         '+61 2 9351 5740'
_publ_contact_author_phone       '+61 2 9351 4391'

_publ_section_title              
;
Experimental charge density of a potential DHO
synthetase inhibitor:
dimethyl-trans-2-oxohexahydro-pyrimidine-4,6-dicarboxylate
;
loop_
_publ_author_name
'Dai E. Hibbs'
'Sian T. Howard'
'Thanh Ha Nguyen'
'Jacob Overgaard'

data_iam
_database_code_depnum_ccdc_archive 'CCDC 253413'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N2 O5'
_chemical_formula_weight         216.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4377(2)
_cell_length_b                   8.3035(2)
_cell_length_c                   9.2515(3)
_cell_angle_alpha                73.265(2)
_cell_angle_beta                 67.994(2)
_cell_angle_gamma                71.219(2)
_cell_volume                     492.34(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      53.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_correction_T_min  0.7252
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'SMART1000 CCD'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13998
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         53.63
_reflns_number_total             9273
_reflns_number_gt                8003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0923P)^2^+0.0416P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         9448
_refine_ls_number_parameters     185
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.134
_refine_ls_shift/su_mean         0.015

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
O1 O 0.76122(5) -0.00452(5) 0.47021(4) 0.01570(5) Uani 1 1 d . . .
O2 O 0.10975(6) 0.50922(5) 0.80622(5) 0.02064(7) Uani 1 1 d . . .
O3 O 0.13675(6) 0.39918(6) 0.60018(5) 0.02049(7) Uani 1 1 d . . .
O4 O 0.71825(9) 0.25920(5) 0.98366(5) 0.02430(9) Uani 1 1 d . . .
O5 O 0.74004(9) 0.00761(5) 0.92448(5) 0.02673(9) Uani 1 1 d . . .
N1 N 0.48968(5) 0.17749(5) 0.60668(5) 0.01400(5) Uani 1 1 d D . .
H01 H 0.4042(13) 0.1383(16) 0.5652(14) 0.042(4) Uiso 1 1 d D . .
N2 N 0.80989(5) 0.16064(5) 0.60388(5) 0.01511(6) Uani 1 1 d D . .
H02 H 0.9586(4) 0.1000(15) 0.5722(14) 0.031(3) Uiso 1 1 d D . .
C1 C 0.68961(5) 0.10501(5) 0.55876(5) 0.01206(5) Uani 1 1 d . . .
C2 C 0.39347(5) 0.28372(5) 0.72833(5) 0.01214(5) Uani 1 1 d D . .
H2 H 0.3510(19) 0.2084(14) 0.8496(6) 0.031(3) Uiso 1 1 d D . .
C3 C 0.53259(6) 0.38929(5) 0.72106(5) 0.01306(5) Uani 1 1 d D . .
H3A H 0.4673(17) 0.4550(13) 0.8222(8) 0.027(3) Uiso 1 1 d D . .
H3B H 0.5499(19) 0.4903(11) 0.6143(8) 0.025(3) Uiso 1 1 d D . .
C4 C 0.73848(6) 0.26986(5) 0.72047(5) 0.01302(5) Uani 1 1 d D . .
H4 H 0.8470(12) 0.3487(11) 0.6855(13) 0.025(3) Uiso 1 1 d D . .
C5 C 0.19953(5) 0.40250(5) 0.70224(5) 0.01315(5) Uani 1 1 d . . .
C6 C -0.07956(7) 0.62769(7) 0.79468(7) 0.02278(9) Uani 1 1 d D . .
H6A H -0.097(2) 0.7259(14) 0.8554(16) 0.051(4) Uiso 1 1 d D . .
H6B H -0.1934(14) 0.5591(15) 0.8604(15) 0.044(4) Uiso 1 1 d D . .
H6C H -0.075(3) 0.674(2) 0.6736(6) 0.058(5) Uiso 1 1 d D . .
C7 C 0.73246(6) 0.16092(5) 0.88619(5) 0.01418(6) Uani 1 1 d . . .
C8 C 0.71001(10) 0.17031(7) 1.14536(7) 0.02553(11) Uani 1 1 d D . .
H8A H 0.5678(10) 0.1416(19) 1.2084(16) 0.051(4) Uiso 1 1 d D . .
H8B H 0.7244(19) 0.2607(13) 1.1997(13) 0.034(3) Uiso 1 1 d D . .
H8C H 0.8281(15) 0.0560(11) 1.1459(17) 0.044(4) Uiso 1 1 d 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
O1 0.01183(10) 0.01965(13) 0.01773(12) -0.01058(9) -0.00472(8) -0.00018(8)
O2 0.01561(12) 0.02049(15) 0.02594(16) -0.01329(12) -0.00632(11) 0.00317(10)
O3 0.01458(12) 0.02472(16) 0.02562(16) -0.01040(12) -0.01031(11) 0.00056(10)
O4 0.0458(3) 0.01638(14) 0.01860(14) -0.00171(10) -0.01721(16) -0.01062(14)
O5 0.0448(3) 0.01309(14) 0.02180(16) -0.00431(10) -0.00952(16) -0.00643(14)
N1 0.00906(9) 0.01659(12) 0.01863(13) -0.00910(9) -0.00418(9) -0.00114(8)
N2 0.00936(10) 0.02075(14) 0.01793(13) -0.00973(10) -0.00368(9) -0.00249(9)
C1 0.00968(10) 0.01439(12) 0.01295(11) -0.00514(9) -0.00358(9) -0.00168(8)
C2 0.01029(10) 0.01239(12) 0.01393(12) -0.00415(8) -0.00329(9) -0.00209(8)
C3 0.01261(12) 0.01274(12) 0.01519(13) -0.00389(9) -0.00499(10) -0.00293(9)
C4 0.01165(11) 0.01487(13) 0.01482(13) -0.00476(9) -0.00472(9) -0.00374(9)
C5 0.00978(11) 0.01277(12) 0.01659(13) -0.00436(9) -0.00303(9) -0.00218(9)
C6 0.01547(15) 0.01700(18) 0.0322(2) -0.00974(15) -0.00458(15) 0.00196(12)
C7 0.01450(13) 0.01321(13) 0.01662(14) -0.00456(9) -0.00634(10) -0.00236(9)
C8 0.0421(3) 0.0204(2) 0.01867(18) -0.00193(14) -0.0156(2) -0.00789(19)

_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
O1 C1 1.2538(5) . ?
O2 C5 1.3361(5) . ?
O2 C6 1.4567(6) . ?
O3 C5 1.2100(6) . ?
O4 C7 1.3369(5) . ?
O4 C8 1.4529(6) . ?
O5 C7 1.2076(6) . ?
N1 C1 1.3614(5) . ?
N1 C2 1.4555(5) . ?
N1 H01 1.0230 . ?
N2 C1 1.3583(5) . ?
N2 C4 1.4463(5) . ?
N2 H02 1.0230 . ?
C2 C5 1.5230(5) . ?
C2 C3 1.5302(5) . ?
C2 H2 1.0990 . ?
C3 C4 1.5322(5) . ?
C3 H3A 1.0920 . ?
C3 H3B 1.0920 . ?
C4 C7 1.5320(6) . ?
C4 H4 1.0990 . ?
C6 H6A 1.0660 . ?
C6 H6B 1.0660 . ?
C6 H6C 1.0660 . ?
C8 H8A 1.0660 . ?
C8 H8B 1.0660 . ?
C8 H8C 1.0660 . ?

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
C5 O2 C6 116.24(4) . . ?
C7 O4 C8 115.69(4) . . ?
C1 N1 C2 123.54(3) . . ?
C1 N1 H01 116.1(6) . . ?
C2 N1 H01 119.7(6) . . ?
C1 N2 C4 124.31(3) . . ?
C1 N2 H02 116.9(7) . . ?
C4 N2 H02 117.3(7) . . ?
O1 C1 N2 121.03(3) . . ?
O1 C1 N1 120.92(3) . . ?
N2 C1 N1 117.98(3) . . ?
N1 C2 C5 108.64(3) . . ?
N1 C2 C3 110.23(3) . . ?
C5 C2 C3 110.80(3) . . ?
N1 C2 H2 113.6(7) . . ?
C5 C2 H2 105.9(7) . . ?
C3 C2 H2 107.6(7) . . ?
C2 C3 C4 109.81(3) . . ?
C2 C3 H3A 109.5(6) . . ?
C4 C3 H3A 110.9(6) . . ?
C2 C3 H3B 111.0(6) . . ?
C4 C3 H3B 108.9(7) . . ?
H3A C3 H3B 106.7(9) . . ?
N2 C4 C7 111.03(3) . . ?
N2 C4 C3 110.92(3) . . ?
C7 C4 C3 110.76(3) . . ?
N2 C4 H4 106.4(6) . . ?
C7 C4 H4 108.2(6) . . ?
C3 C4 H4 109.3(5) . . ?
O3 C5 O2 125.07(4) . . ?
O3 C5 C2 123.80(4) . . ?
O2 C5 C2 111.13(3) . . ?
O2 C6 H6A 103.4(8) . . ?
O2 C6 H6B 107.2(7) . . ?
H6A C6 H6B 108.9(11) . . ?
O2 C6 H6C 110.7(9) . . ?
H6A C6 H6C 114.1(12) . . ?
H6B C6 H6C 112.1(13) . . ?
O5 C7 O4 124.30(4) . . ?
O5 C7 C4 125.19(4) . . ?
O4 C7 C4 110.51(3) . . ?
O4 C8 H8A 110.3(8) . . ?
O4 C8 H8B 105.6(7) . . ?
H8A C8 H8B 107.8(11) . . ?
O4 C8 H8C 110.7(8) . . ?
H8A C8 H8C 111.4(11) . . ?
H8B C8 H8C 111.0(11) . . ?

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 O1 -172.12(4) . . . . ?
C4 N2 C1 N1 10.78(7) . . . . ?
C2 N1 C1 O1 169.96(4) . . . . ?
C2 N1 C1 N2 -12.94(6) . . . . ?
C1 N1 C2 C5 155.72(4) . . . . ?
C1 N1 C2 C3 34.14(5) . . . . ?
N1 C2 C3 C4 -50.57(4) . . . . ?
C5 C2 C3 C4 -170.86(3) . . . . ?
C1 N2 C4 C7 93.44(5) . . . . ?
C1 N2 C4 C3 -30.16(6) . . . . ?
C2 C3 C4 N2 48.88(4) . . . . ?
C2 C3 C4 C7 -74.88(4) . . . . ?
C6 O2 C5 O3 0.94(7) . . . . ?
C6 O2 C5 C2 -179.05(4) . . . . ?
N1 C2 C5 O3 3.09(6) . . . . ?
C3 C2 C5 O3 124.33(5) . . . . ?
N1 C2 C5 O2 -176.92(4) . . . . ?
C3 C2 C5 O2 -55.68(4) . . . . ?
C8 O4 C7 O5 -0.59(9) . . . . ?
C8 O4 C7 C4 179.63(5) . . . . ?
N2 C4 C7 O5 -16.11(6) . . . . ?
C3 C4 C7 O5 107.59(6) . . . . ?
N2 C4 C7 O4 163.67(4) . . . . ?
C3 C4 C7 O4 -72.63(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.788
_diffrn_reflns_theta_full        53.63
_diffrn_measured_fraction_theta_full 0.788
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.117

loop_
_atom_rho_multipole_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa_prime
_atom_rho_multipole_kappa_dprime0
_atom_rho_multipole_kappa_dprime1
_atom_rho_multipole_kappa_dprime2
_atom_rho_multipole_kappa_dprime3
_atom_rho_multipole_kappa_dprime4
O(1) 6.30(3) 0.00 -0.102(14) 0.017(12) 0.00 -0.053(13) 0.00 0.00 -0.112(11)
0.008(11) 0.00 -0.034(10) 0.012(9) 0.00 0.00 0.043(9) -0.005(9) 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.995(2) 0.93 0.93 0.93 0.93 0.93
O(2) 6.28(3) 0.00 -0.016(14) -0.061(15) 0.00 0.022(15) 0.00 0.00 -0.009(12)
0.014(13) 0.00 0.004(10) -0.025(11) 0.00 0.00 0.113(10) -0.001(11) 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.000(3) 0.93 0.93 0.93 0.93 0.93
O(3) 6.19(3) 0.00 -0.007(18) -0.018(14) 0.00 -0.132(16) 0.00 0.00 -0.023(12)
-0.038(14) 0.00 -0.005(11) 0.014(10) 0.00 0.00 0.033(10) -0.022(10) 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.995(2) 0.93 0.93 0.93 0.93 0.93
O(4) 6.30(3) 0.00 0.013(16) -0.038(15) 0.00 -0.015(17) 0.00 0.00 -0.027(14)
0.029(14) 0.00 0.051(11) -0.013(11) 0.00 0.00 0.118(10) 0.053(11) 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.000(3) 0.93 0.93 0.93 0.93 0.93
O(5) 6.29(4) 0.00 -0.01(2) 0.023(17) 0.00 -0.21(2) 0.00 0.00 -0.061(16)
-0.037(15) 0.00 0.046(13) 0.041(11) 0.00 0.00 0.043(10) 0.036(10) 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.995(2) 0.93 0.93 0.93 0.93 0.93
N(1) 5.54(5) 0.00 -0.061(17) -0.076(17) -0.023(15) -0.002(14) 0.009(13)
0.023(12) -0.058(15) 0.063(14) 0.079(13) -0.003(12) 0.008(12) 0.082(13)
-0.040(13) 0.307(14) 0.042(14) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.976(3) 0.80 0.80 0.80 0.80 0.80
N(2) 5.53(5) 0.00 -0.055(19) -0.060(17) 0.050(15) -0.025(14) -0.021(14)
-0.038(13) -0.038(16) 0.018(14) -0.082(14) -0.006(13) 0.026(12) -0.063(13)
0.037(13) 0.331(14) 0.052(14) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.976(3) 0.80 0.80 0.80 0.80 0.80
C(1) 3.83(4) 0.00 -0.12(2) -0.17(2) -0.016(15) -0.431(17) 0.004(15) -0.005(14)
-0.12(2) 0.18(2) -0.050(17) 0.016(17) 0.014(17) -0.001(18) -0.020(17) 0.62(2)
-0.06(3) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.015(3) 0.78 0.78 0.78
0.78 0.78
C(2) 4.00(3) 0.00 0.05(2) -0.14(2) -0.218(19) 0.019(16) 0.042(17) 0.132(17)
0.090(19) 0.032(18) 0.004(17) -0.241(18) -0.335(17) 0.006(19) -0.127(18)
0.337(17) -0.08(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.015(3) 0.78
0.78 0.78 0.78 0.78
C(3) 4.30(3) 0.00 -0.11(2) -0.24(2) 0.041(15) 0.125(17) -0.047(15) 0.020(14)
-0.016(18) 0.056(18) 0.003(15) -0.244(16) -0.343(17) -0.023(17) -0.001(15)
0.295(17) -0.058(18) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.015(3) 0.78
0.78 0.78 0.78 0.78
C(4) 4.06(3) 0.00 0.06(2) -0.21(2) -0.15(2) 0.048(18) 0.005(17) 0.083(17)
0.06(2) 0.069(17) -0.033(18) -0.202(18) -0.364(17) -0.012(19) 0.012(18)
0.322(18) -0.03(2) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.015(3) 0.78
0.78 0.78 0.78 0.78
C(5) 4.10(4) 0.00 0.17(3) -0.07(2) 0.00 -0.422(17) 0.00 0.00 0.16(2) 0.10(2)
0.00 0.047(18) -0.045(16) 0.00 0.00 0.72(2) 0.03(3) 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 1.015(3) 0.78 0.78 0.78 0.78 0.78
C(6) 4.34(3) 0.00 -0.032(13) 0.091(13) -0.236(18) -0.171(16) -0.054(12)
-0.034(13) 0.053(12) -0.046(13) 0.540(19) 0.069(14) 0.094(15) 0.008(14)
0.061(14) -0.037(13) -0.171(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
1.015(3) 0.78 0.78 0.78 0.78 0.78
C(7) 4.11(4) 0.00 0.11(3) -0.10(2) 0.00 -0.433(16) 0.00 0.00 0.19(2) 0.00(2)
0.00 0.044(19) -0.064(16) 0.00 0.00 0.61(2) 0.06(3) 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 1.015(3) 0.78 0.78 0.78 0.78 0.78
C(8) 4.32(4) 0.00 -0.112(14) -0.020(14) -0.244(17) -0.129(16) 0.021(14)
-0.009(13) 0.024(13) 0.008(14) 0.508(19) -0.034(16) 0.116(15) 0.035(14)
-0.070(14) -0.011(14) -0.263(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
1.015(3) 0.78 0.78 0.78 0.78 0.78
H(01) 0.582(16) 0.00 0.00 0.00 0.091(10) 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20
1.20 1.20 1.20 1.20
H(02) 0.58 0.00 0.00 0.00 0.09 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(2) 0.716(15) 0.00 0.00 0.00 0.105(9) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(3A) 0.777(14) 0.00 0.00 0.00 0.073(8) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(3B) 0.78 0.00 0.00 0.00 0.07 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(4) 0.72 0.00 0.00 0.00 0.10 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20
1.20
H(6A) 0.729(10) 0.00 0.00 0.00 0.115(6) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20
1.20 1.20 1.20
H(6B) 0.73 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(6C) 0.73 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8A) 0.73 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8B) 0.73 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
H(8C) 0.73 0.00 0.00 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00
0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20
1.20 1.20
loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) X O(1) N(2) Y
O(2) C(5) X O(2) C(6) Y
O(3) C(5) X O(3) O(2) Y
O(4) C(7) X O(4) C(8) Y
O(5) C(7) X O(5) O(4) Y
N(1) C(2) X N(1) C(1) Y
N(2) C(4) X N(2) C(1) Y
C(1) N(1) X C(1) N(2) Y
C(2) C(3) X C(2) N(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) N(2) Y
C(5) O(3) X C(5) O(2) Y
C(6) O(2) Z C(6) H(6C) Y
C(7) O(5) X C(7) O(4) Y
C(8) O(4) Z C(8) H(8C) Y
H(01) N(1) Z H(01) C(1) Y
H(02) N(2) Z H(02) C(1) Y
H(2) C(2) Z H(2) C(5) Y
H(3A) C(3) Z H(3A) H(3B) Y
H(3B) C(3) Z H(3B) H(3A) Y
H(4) C(4) Z H(4) N(2) Y
H(6A) C(6) Z H(6A) H(6B) Y
H(6B) C(6) Z H(6B) H(6A) Y
H(6C) C(6) Z H(6C) H(6B) Y
H(8A) C(8) Z H(8A) H(8B) Y
H(8B) C(8) Z H(8B) H(8A) Y
H(8C) C(8) Z H(8C) H(8A) Y