#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223721.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2223721
loop_
_publ_author_name
'Tang, Huang'
'Cheng, Feng-Jie'
'Li, Nan'
'Liu, Yan-Cheng'
'Chen, Zhen-Feng'
_publ_section_title
;
 9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine monohydrate
;
_journal_coeditor_code           DS2005
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2878
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H15 N5 O3, H2 O'
_chemical_formula_moiety         'C10 H15 N5 O3, H2 O'
_chemical_formula_sum            'C10 H17 N5 O4'
_chemical_formula_weight         271.29
_chemical_name_systematic
;
9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2020(16)
_cell_length_b                   13.889(3)
_cell_length_c                   11.001(2)
_cell_measurement_reflns_used    1193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      3.42
_cell_volume                     1253.2(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0748
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6830
_diffrn_reflns_theta_full        25.23
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         3.43
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1193
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0504
_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/[\s^2^(Fo^2^)+(0.0604P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                1084
_reflns_number_total             1193
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ds2005.cif
_[local]_cod_data_source_block   I
_[local]_cod_chemical_formula_sum_orig 'C10 H17 N5 O4 '
_cod_database_code               2223721
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.0269(5) 0.4750(3) 0.0559(4) 0.0321(9) Uani d . 1
C C2 -0.0398(5) 0.3455(3) -0.0873(4) 0.0354(9) Uani d . 1
C C3 -0.0027(5) 0.3211(3) 0.3070(4) 0.0374(10) Uani d . 1
H H3 -0.0018 0.3037 0.3886 0.045 Uiso calc R 1
C C4 -0.0242(5) 0.3102(2) 0.1084(4) 0.0311(9) Uani d . 1
C C5 0.0189(5) -0.0152(3) 0.2010(4) 0.0375(9) Uani d . 1
H H5 -0.0741 -0.0176 0.1452 0.045 Uiso calc R 1
C C6 0.0126(5) 0.4027(3) 0.1448(4) 0.0323(9) Uani d . 1
C C7 -0.0735(5) 0.1556(3) 0.2279(4) 0.0396(10) Uani d . 1
H H7A -0.1567 0.1390 0.1689 0.048 Uiso calc R 1
H H7B -0.1185 0.1448 0.3083 0.048 Uiso calc R 1
C C8 0.0713(5) 0.0901(3) 0.2102(5) 0.0383(9) Uani d . 1
H H8A 0.1458 0.0977 0.2780 0.046 Uiso calc R 1
H H8B 0.1286 0.1084 0.1366 0.046 Uiso calc R 1
C C9 -0.0360(6) -0.0601(3) 0.3195(5) 0.0537(13) Uani d . 1
H H9A -0.1190 -0.0197 0.3563 0.064 Uiso calc R 1
H H9B -0.0841 -0.1226 0.3032 0.064 Uiso calc R 1
C C10 0.1551(5) -0.0729(3) 0.1431(4) 0.0424(11) Uani d . 1
H H10A 0.1837 -0.0435 0.0660 0.051 Uiso calc R 1
H H10B 0.2504 -0.0699 0.1952 0.051 Uiso calc R 1
N N1 -0.0334(4) 0.2576(2) 0.2150(3) 0.0352(8) Uani d . 1
N N2 0.0253(4) 0.4092(2) 0.2691(3) 0.0356(8) Uani d . 1
N N3 -0.0498(4) 0.2759(2) -0.0038(3) 0.0354(8) Uani d . 1
N N4 -0.0054(4) 0.4399(2) -0.0607(4) 0.0359(8) Uani d . 1
N N5 -0.0645(5) 0.3259(3) -0.2040(4) 0.0506(10) Uani d . 1
H H5A -0.0871 0.2680 -0.2263 0.061 Uiso calc R 1
H H5B -0.0579 0.3710 -0.2573 0.061 Uiso calc R 1
O O1 0.0604(4) 0.56135(18) 0.0709(3) 0.0396(7) Uani d . 1
O O2 0.1144(4) -0.17160(18) 0.1226(3) 0.0485(8) Uani d . 1
H H2 0.0219 -0.1752 0.0948 0.073 Uiso calc R 1
O O3 0.0950(6) -0.0711(3) 0.4012(4) 0.0760(12) Uani d . 1
H H3A 0.0878 -0.1234 0.4354 0.114 Uiso calc R 1
O O4 0.1827(4) 0.1915(2) 0.5157(4) 0.0518(8) Uani d D 1
H H4 -0.017(7) 0.489(4) -0.119(6) 0.068(17) Uiso d . 1
H H4A 0.243(6) 0.234(3) 0.549(5) 0.069(17) Uiso d D 1
H H4B 0.222(9) 0.1362(19) 0.527(8) 0.14(3) Uiso d D 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.036(2) 0.029(2) 0.031(2) -0.0005(16) -0.0003(17) -0.0003(17)
C2 0.045(2) 0.031(2) 0.031(2) 0.0021(16) 0.0000(18) -0.0032(19)
C3 0.050(2) 0.032(2) 0.030(2) 0.0036(17) 0.0007(19) 0.0023(18)
C4 0.040(2) 0.0252(18) 0.028(2) 0.0044(15) -0.0008(18) -0.0019(17)
C5 0.043(2) 0.031(2) 0.039(3) -0.0014(16) 0.000(2) 0.003(2)
C6 0.041(2) 0.0264(18) 0.029(2) 0.0027(15) -0.0015(17) -0.0031(17)
C7 0.051(2) 0.0270(19) 0.041(3) -0.0016(17) 0.0036(19) 0.0063(19)
C8 0.041(2) 0.0288(19) 0.045(3) -0.0016(16) -0.003(2) 0.0041(19)
C9 0.059(3) 0.042(3) 0.060(4) -0.004(2) 0.014(3) 0.006(2)
C10 0.050(2) 0.033(2) 0.045(3) -0.0005(17) 0.008(2) 0.0043(19)
N1 0.053(2) 0.0217(14) 0.031(2) 0.0013(13) 0.0017(18) 0.0038(15)
N2 0.0508(19) 0.0308(16) 0.025(2) 0.0009(15) 0.0000(16) -0.0018(15)
N3 0.0492(19) 0.0296(17) 0.028(2) -0.0021(15) 0.0012(15) -0.0013(15)
N4 0.053(2) 0.0274(17) 0.028(2) -0.0031(14) 0.0004(16) 0.0017(15)
N5 0.088(3) 0.0347(18) 0.029(2) -0.0071(18) -0.005(2) -0.0013(16)
O1 0.0618(18) 0.0260(13) 0.0311(18) -0.0097(13) 0.0054(13) -0.0011(12)
O2 0.0553(17) 0.0275(13) 0.063(2) 0.0027(12) 0.0003(17) -0.0004(15)
O3 0.109(3) 0.066(2) 0.053(3) -0.018(2) -0.018(2) 0.0180(19)
O4 0.0547(18) 0.0418(17) 0.059(2) 0.0001(16) -0.0074(17) 0.0026(16)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N4 120.1(4)
O1 C1 C6 128.0(4)
N4 C1 C6 111.9(3)
N5 C2 N3 120.4(4)
N5 C2 N4 115.7(4)
N3 C2 N4 123.9(4)
N2 C3 N1 113.5(4)
N2 C3 H3 123.2
N1 C3 H3 123.2
N3 C4 C6 129.3(4)
N3 C4 N1 125.8(3)
C6 C4 N1 104.9(4)
C9 C5 C10 111.3(3)
C9 C5 C8 114.9(4)
C10 C5 C8 109.1(3)
C9 C5 H5 107.0
C10 C5 H5 107.0
C8 C5 H5 107.0
N2 C6 C4 111.5(4)
N2 C6 C1 129.7(4)
C4 C6 C1 118.8(4)
N1 C7 C8 113.3(3)
N1 C7 H7A 108.9
C8 C7 H7A 108.9
N1 C7 H7B 108.9
C8 C7 H7B 108.9
H7A C7 H7B 107.7
C7 C8 C5 111.4(3)
C7 C8 H8A 109.3
C5 C8 H8A 109.3
C7 C8 H8B 109.3
C5 C8 H8B 109.3
H8A C8 H8B 108.0
O3 C9 C5 111.5(4)
O3 C9 H9A 109.3
C5 C9 H9A 109.3
O3 C9 H9B 109.3
C5 C9 H9B 109.3
H9A C9 H9B 108.0
O2 C10 C5 113.7(3)
O2 C10 H10A 108.8
C5 C10 H10A 108.8
O2 C10 H10B 108.8
C5 C10 H10B 108.8
H10A C10 H10B 107.7
C3 N1 C4 106.1(3)
C3 N1 C7 126.6(4)
C4 N1 C7 127.3(4)
C3 N2 C6 104.0(4)
C2 N3 C4 111.5(3)
C2 N4 C1 124.6(4)
C2 N4 H4 122(4)
C1 N4 H4 113(4)
C2 N5 H5A 120.0
C2 N5 H5B 120.0
H5A N5 H5B 120.0
C10 O2 H2 109.5
C9 O3 H3A 109.5
H4A O4 H4B 110(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.241(5)
C1 N4 1.397(6)
C1 C6 1.407(6)
C2 N5 1.329(6)
C2 N3 1.336(5)
C2 N4 1.372(5)
C3 N2 1.312(5)
C3 N1 1.366(6)
C3 H3 0.9300
C4 N3 1.340(5)
C4 C6 1.379(5)
C4 N1 1.383(5)
C5 C9 1.514(7)
C5 C10 1.515(6)
C5 C8 1.528(5)
C5 H5 0.9800
C6 N2 1.375(5)
C7 N1 1.461(5)
C7 C8 1.508(6)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C9 O3 1.410(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O2 1.429(5)
C10 H10A 0.9700
C10 H10B 0.9700
N4 H4 0.94(6)
N5 H5A 0.8600
N5 H5B 0.8600
O2 H2 0.8200
O3 H3A 0.8200
O4 H4A 0.85(5)
O4 H4B 0.84(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 O4 2_554 0.82000 1.90000 2.719(3) 175
O3 H3A N3 2_555 0.82000 2.24000 3.052(3) 169
N4 H4 N2 2_564 0.96(3) 1.86(3) 2.816(3) 176(3)
O4 H4A O2 4_555 0.86(3) 1.93(3) 2.787(3) 178(3)
O4 H4B O1 4_545 0.84(3) 2.11(5) 2.842(3) 146(3)
N5 H5A O2 2_554 0.86000 2.15000 2.898(3) 146
N5 H5B O1 2_564 0.86000 2.11000 2.931(3) 159
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
N3 C4 C6 N2 178.4(4)
N1 C4 C6 N2 -0.4(4)
N3 C4 C6 C1 0.1(6)
N1 C4 C6 C1 -178.6(3)
O1 C1 C6 N2 2.8(7)
N4 C1 C6 N2 -175.9(4)
O1 C1 C6 C4 -179.3(4)
N4 C1 C6 C4 2.0(5)
N1 C7 C8 C5 -169.4(4)
C9 C5 C8 C7 -72.7(5)
C10 C5 C8 C7 161.5(4)
C10 C5 C9 O3 56.0(5)
C8 C5 C9 O3 -68.6(5)
C9 C5 C10 O2 56.1(5)
C8 C5 C10 O2 -176.0(4)
N2 C3 N1 C4 -0.1(4)
N2 C3 N1 C7 -178.1(3)
N3 C4 N1 C3 -178.5(4)
C6 C4 N1 C3 0.3(4)
N3 C4 N1 C7 -0.5(6)
C6 C4 N1 C7 178.3(3)
C8 C7 N1 C3 -98.2(5)
C8 C7 N1 C4 84.2(5)
N1 C3 N2 C6 -0.2(5)
C4 C6 N2 C3 0.3(5)
C1 C6 N2 C3 178.4(4)
N5 C2 N3 C4 -178.8(4)
N4 C2 N3 C4 0.8(5)
C6 C4 N3 C2 -1.6(6)
N1 C4 N3 C2 176.9(4)
N5 C2 N4 C1 -178.9(4)
N3 C2 N4 C1 1.4(6)
O1 C1 N4 C2 178.4(4)
C6 C1 N4 C2 -2.8(5)