#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:32:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180226 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/12/7111205.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111205
loop_
_publ_author_name
'Davies, R. Jeremy H.'
'Stevenson, Clarke'
'Kumar, Shiv'
'Lyle, Jason'
'Cosby, Lisa'
'Malone, John F.'
'Boyd, Derek R.'
'Sharma, Narain D.'
'Hunter, Ann P.'
'Stein, Bridget K.'
_publ_section_title
;
 Novel oxidation products from guanine nucleosides reacted with
 dimethyldioxirane
;
_journal_issue                   13
_journal_name_full               'Chemical Communications'
_journal_page_first              1378
_journal_paper_doi               10.1039/b201418c
_journal_year                    2002
_chemical_formula_sum            'C5 H8 Cl N5 O6'
_chemical_formula_weight         269.61
_chemical_name_common
'4-amidiniumcarbamoyl-5-hydroxyimidazole perchlorate'
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.444(7)
_cell_angle_beta                 94.615(7)
_cell_angle_gamma                91.416(7)
_cell_formula_units_Z            2
_cell_length_a                   4.825(3)
_cell_length_b                   9.812(5)
_cell_length_c                   10.052(5)
_cell_measurement_temperature    150(2)
_cell_volume                     466.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5488
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plates'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    refined
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                1359
_reflns_number_total             2123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b201418csup1.cif
_cod_data_source_block           1.HClO4
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7111205
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.2318(6) 1.1369(3) 0.9706(3) 0.0187(6) Uani 1 1 d
H1 H 0.127(9) 1.135(4) 1.032(4) 0.042(13) Uiso 1 1 d
C2 C 0.4048(7) 1.2429(4) 0.9634(4) 0.0201(7) Uani 1 1 d
H2 H 0.423(6) 1.327(3) 1.015(3) 0.009(8) Uiso 1 1 d
N3 N 0.5642(6) 1.2061(3) 0.8650(3) 0.0188(6) Uani 1 1 d
H3 H 0.667(9) 1.257(5) 0.838(4) 0.049(14) Uiso 1 1 d
C4 C 0.4977(6) 1.0690(3) 0.8035(3) 0.0169(7) Uani 1 1 d
C5 C 0.2822(7) 1.0230(3) 0.8722(3) 0.0186(7) Uani 1 1 d
O5 O 0.1565(5) 0.9069(2) 0.8541(2) 0.0214(5) Uani 1 1 d
C1' C 0.6221(7) 0.9972(3) 0.6891(3) 0.0185(7) Uani 1 1 d
O1' O 0.8043(5) 1.0471(2) 0.6310(2) 0.0226(6) Uani 1 1 d
N2' N 0.5100(7) 0.8629(3) 0.6462(3) 0.0198(7) Uani 1 1 d
H2' H 0.415(9) 0.843(5) 0.676(4) 0.032(15) Uiso 1 1 d
C3' C 0.5686(7) 0.7727(3) 0.5351(3) 0.0184(7) Uani 1 1 d
N4' N 0.4180(6) 0.6569(3) 0.4987(3) 0.0208(7) Uani 1 1 d
H4'A H 0.285(9) 0.645(4) 0.545(4) 0.040(13) Uiso 1 1 d
H4'B H 0.428(7) 0.604(3) 0.430(3) 0.008(9) Uiso 1 1 d
N5' N 0.7775(6) 0.8013(3) 0.4661(3) 0.0202(6) Uani 1 1 d
H5'A H 0.868(8) 0.885(4) 0.501(4) 0.035(11) Uiso 1 1 d
H5'B H 0.819(7) 0.744(4) 0.396(4) 0.023(10) Uiso 1 1 d
Cl1 Cl 0.10368(16) 0.51630(8) 0.77766(8) 0.0190(2) Uani 1 1 d
O1 O -0.0086(5) 0.3764(2) 0.7658(2) 0.0236(6) Uani 1 1 d
O2 O 0.4010(4) 0.5099(3) 0.7697(2) 0.0264(6) Uani 1 1 d
O3 O 0.0452(5) 0.5987(2) 0.9028(2) 0.0263(6) Uani 1 1 d
O4 O -0.0161(5) 0.5737(3) 0.6645(2) 0.0280(6) 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
N1 0.0147(15) 0.0224(15) 0.0195(16) 0.0022(12) 0.0082(12) -0.0016(12)
C2 0.0153(18) 0.0211(18) 0.0227(19) 0.0002(15) 0.0031(14) 0.0001(14)
N3 0.0128(15) 0.0203(15) 0.0241(16) 0.0040(12) 0.0067(12) 0.0004(12)
C4 0.0105(16) 0.0191(17) 0.0209(18) 0.0024(14) 0.0042(13) -0.0007(13)
C5 0.0140(17) 0.0238(18) 0.0183(17) 0.0034(14) 0.0034(13) 0.0005(14)
O5 0.0164(12) 0.0205(12) 0.0274(14) 0.0024(10) 0.0085(10) -0.0028(10)
C1' 0.0129(17) 0.0250(18) 0.0190(18) 0.0066(14) 0.0045(13) -0.0001(14)
O1' 0.0174(13) 0.0252(13) 0.0262(13) 0.0046(10) 0.0099(10) -0.0027(10)
N2' 0.0151(16) 0.0206(16) 0.0229(17) -0.0013(13) 0.0099(13) -0.0033(13)
C3' 0.0153(17) 0.0214(18) 0.0191(18) 0.0044(14) 0.0026(13) 0.0005(14)
N4' 0.0173(16) 0.0216(16) 0.0221(18) -0.0019(14) 0.0085(13) -0.0027(12)
N5' 0.0165(15) 0.0214(16) 0.0230(17) 0.0003(13) 0.0129(12) -0.0034(12)
Cl1 0.0119(4) 0.0234(4) 0.0213(5) 0.0018(3) 0.0060(3) -0.0020(3)
O1 0.0205(13) 0.0220(12) 0.0276(14) 0.0005(10) 0.0089(10) -0.0043(10)
O2 0.0064(12) 0.0390(15) 0.0321(14) 0.0008(12) 0.0059(10) -0.0021(10)
O3 0.0264(14) 0.0265(13) 0.0239(14) -0.0045(11) 0.0109(11) -0.0011(11)
O4 0.0207(13) 0.0402(15) 0.0254(14) 0.0128(11) 0.0015(11) -0.0031(11)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C5 109.8(3)
N3 C2 N1 109.4(3)
C2 N3 C4 109.4(3)
N3 C4 C5 106.6(3)
N3 C4 C1' 124.5(3)
C5 C4 C1' 128.8(3)
O5 C5 N1 125.3(3)
O5 C5 C4 129.9(3)
N1 C5 C4 104.7(3)
O1' C1' N2' 122.8(3)
O1' C1' C4 124.8(3)
N2' C1' C4 112.4(3)
C3' N2' C1' 126.6(3)
N4' C3' N5' 121.3(3)
N4' C3' N2' 119.0(3)
N5' C3' N2' 119.7(3)
O3 Cl1 O1 110.63(14)
O3 Cl1 O4 110.73(16)
O1 Cl1 O4 108.54(15)
O3 Cl1 O2 110.13(15)
O1 Cl1 O2 107.99(14)
O4 Cl1 O2 108.76(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.333(4)
N1 C5 1.392(4)
C2 N3 1.307(4)
N3 C4 1.393(4)
C4 C5 1.402(4)
C4 C1' 1.420(5)
C5 O5 1.254(4)
C1' O1' 1.233(4)
C1' N2' 1.392(4)
N2' C3' 1.347(4)
C3' N4' 1.311(4)
C3' N5' 1.321(4)
Cl1 O3 1.420(2)
Cl1 O1 1.444(2)
Cl1 O4 1.445(2)
Cl1 O2 1.445(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C2 N3 0.7(4)
N1 C2 N3 C4 -0.4(4)
C2 N3 C4 C5 0.0(4)
C2 N3 C4 C1' 177.2(3)
C2 N1 C5 O5 179.0(3)
C2 N1 C5 C4 -0.7(4)
N3 C4 C5 O5 -179.2(3)
C1' C4 C5 O5 3.7(6)
N3 C4 C5 N1 0.4(3)
C1' C4 C5 N1 -176.6(3)
N3 C4 C1' O1' 0.4(5)
C5 C4 C1' O1' 177.0(3)
N3 C4 C1' N2' -178.1(3)
C5 C4 C1' N2' -1.5(5)
O1' C1' N2' C3' -3.8(5)
C4 C1' N2' C3' 174.7(3)
C1' N2' C3' N4' -170.9(3)
C1' N2' C3' N5' 9.9(5)
