#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/28/2102837.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_2102837
loop_
_publ_author_name
'Bendeif, El-Eulmi'
'Dahaoui, Slimane'
'Benali-Cherif, Nourredine'
'Lecomte, Claude'
_publ_section_title
;
 Tautomerism and hydrogen bonding in guaninium phosphite and guaninium
 phosphate salts
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              448
_journal_page_last               458
_journal_paper_doi               10.1107/S0108768107005332
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '(C5 H6 N5 O 1) +,(H2 P O4) -,H2 O '
_chemical_formula_moiety         'C5 H6 N5 O 1+, H2 O4 P 1-, H2 O'
_chemical_formula_structural     'C5 H10 N5 O6 P1'
_chemical_formula_sum            'C5 H10 N5 O6 P'
_chemical_formula_weight         267.15
_chemical_name_common            'Guaninium phosphate monohydrate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.689(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5414(3)
_cell_length_b                   12.5774(6)
_cell_length_c                   18.1485(9)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.74
_cell_volume                     1034.48(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.703
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Xcalibur-Saphire2
_diffrn_measurement_method       φ
_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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            42941
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Absorb, (DeTitta, 1985)'
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0422
_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)+(0.0640P)²+0.5194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2971
_reflns_number_total             3013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lb5008.cif
_cod_data_source_block           GPO4
_cod_original_formula_sum        'C5 H10 N5 O6 P1'
_cod_database_code               2102837
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
O O6 0.7880(2) 0.47228(8) 0.26876(6) 0.0163(2) Uani d 1
N N7 0.5312(2) 0.70398(9) 0.27694(6) 0.0119(2) Uani d 1
N N9 0.2068(2) 0.73788(9) 0.35871(6) 0.0125(2) Uani d 1
N N2 0.1965(3) 0.38974(10) 0.45533(7) 0.0163(2) Uani d 1
C C4 0.2893(3) 0.63332(10) 0.36871(7) 0.0110(2) Uani d 1
N N1 0.4863(2) 0.43853(9) 0.36100(6) 0.0123(2) Uani d 1
C C8 0.3576(3) 0.77713(10) 0.30321(7) 0.0132(2) Uani d 1
N N3 0.1828(2) 0.56524(9) 0.41787(6) 0.0124(2) Uani d 1
C C6 0.6063(3) 0.50706(10) 0.31146(7) 0.0118(2) Uani d 1
C C2 0.2857(3) 0.46676(10) 0.41152(7) 0.0118(2) Uani d 1
C C5 0.4939(3) 0.61158(10) 0.31720(7) 0.0117(2) Uani d 1
P P1 0.53006(7) 0.13870(2) 0.38133(2) 0.00980(10) Uani d 1
O O3 0.7942(2) 0.07895(8) 0.42348(6) 0.0145(2) Uani d 1
O O1 0.3013(2) 0.16979(8) 0.43410(5) 0.01273(19) Uani d 1
O O2 0.6455(2) 0.23068(8) 0.33815(5) 0.0138(2) Uani d 1
O O4 0.3817(2) 0.05213(8) 0.32854(6) 0.0146(2) Uani d 1
O O1W 0.7969(2) 0.85448(8) 0.41964(6) 0.0154(2) Uani d 1
H H8 0.341(5) 0.8484(16) 0.2869(11) 0.017(5) Uiso d 1
H H21 0.091(5) 0.4023(18) 0.4890(13) 0.024(5) Uiso d 1
H H1 0.539(5) 0.3695(19) 0.3581(13) 0.029(6) Uiso d 1
H H9 0.068(5) 0.775(2) 0.3853(14) 0.034(6) Uiso d 1
H H22 0.238(5) 0.3225(19) 0.4475(12) 0.024(5) Uiso d 1
H H7 0.637(7) 0.719(2) 0.2368(17) 0.054(8) Uiso d 1
H H12 0.740(6) 0.846(2) 0.4631(16) 0.040(7) Uiso d 1
H H11 0.820(6) 0.916(3) 0.4158(16) 0.047(8) Uiso d 1
H H4 0.500(7) 0.034(2) 0.2964(17) 0.051(8) Uiso d 1
H H3 0.972(6) 0.110(2) 0.4236(13) 0.033(6) Uiso d 1
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C8 N7 C5 107.29(11)
C8 N9 C4 107.55(11)
N3 C4 N9 126.00(11)
N3 C4 C5 127.23(12)
N9 C4 C5 106.74(11)
C2 N1 C6 125.20(11)
N7 C8 N9 111.01(12)
C2 N3 C4 112.99(11)
O6 C6 N1 119.32(12)
O6 C6 C5 128.84(12)
N1 C6 C5 111.83(11)
N3 C2 N2 120.17(12)
N3 C2 N1 123.18(12)
N2 C2 N1 116.65(12)
C4 C5 N7 107.41(11)
C4 C5 C6 119.52(12)
N7 C5 C6 132.94(12)
O1 P1 O2 114.01(6)
O1 P1 O3 110.49(6)
O2 P1 O3 109.84(6)
O1 P1 O4 106.30(6)
O2 P1 O4 111.32(6)
O3 P1 O4 104.42(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O6 C6 1.2470(16)
N7 C8 1.3205(17)
N7 C5 1.3888(16)
N9 C8 1.3475(17)
N9 C4 1.3762(16)
N2 C2 1.3328(17)
C4 N3 1.3486(16)
C4 C5 1.3870(17)
N1 C2 1.3798(16)
N1 C6 1.3825(16)
N3 C2 1.3315(16)
C6 C5 1.4165(18)
P1 O1 1.5090(9)
P1 O2 1.5100(10)
P1 O3 1.5717(10)
P1 O4 1.5729(10)
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
O(3) H(3) O(1) 1_655 0.90(3) 1.67(3) 2.5670(10) 174(2)
O(4) H(4) O(6) 2_645 0.85(3) 1.75(3) 2.5920(10) 169(3)
N(7) H(7) O(2) 2_655 0.92(3) 1.74(3) 2.651(2) 173(3)
N(9) H(9) O(1W) 1_455 0.94(2) 1.73(2) 2.665(2) 170(2)
O(1W) H(12) O(1) 3_666 0.85(3) 1.90(3) 2.7370(10) 168(3)
N(1) H(1) O(2) 1_555 0.90(2) 1.85(2) 2.751(2) 172(2)
O(1W) H(11) O(3) 1_565 0.78(4) 2.06(4) 2.8240(10) 165(3)
N(2) H(22) O(1) 1_555 0.88(2) 1.96(2) 2.838(2) 175(2)
N(2) H(21) N(3) 3_566 0.82(2) 2.20(2) 3.016(2) 178(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21139980
2 PubChem 139063615
