#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227096.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_2227096
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Guanidinium phenylarsonate--guanidine--water (1/1/2)
;
_journal_coeditor_code           TK2684
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1893
_journal_page_last               o1894
_journal_paper_doi               10.1107/S1600536810025043
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C H6 N3 +, C6 H6 As O3 -, C H5 N3, 2H2 O'
_chemical_formula_moiety         'C H6 N3 +, C6 H6 As O3 -, C H5 N3, 2(H2 O)'
_chemical_formula_sum            'C8 H21 As N6 O5'
_chemical_formula_weight         356.23
_chemical_melting_point          505
_chemical_name_common            'guanidinium phenylarsonate guanidine dihyrate'
_chemical_name_systematic
;
Guanidinium phenylarsonate--guanidine--water (1/1/2)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.856(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.6545(14)
_cell_length_b                   7.6394(3)
_cell_length_c                   12.6319(10)
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      3.12
_cell_volume                     1529.0(2)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.08
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4919
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.216
_refine_ls_abs_structure_details 'Flack (1983), 590 Friedel pairs'
_refine_ls_abs_structure_Flack   0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0159P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0352
_refine_ls_wR_factor_ref         0.0354
_reflns_number_gt                1940
_reflns_number_total             2095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2684.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2227096
_cod_database_fobs_code          2227096
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
As As1 0.854720(10) 0.69726(3) 0.45636(2) 0.01620(10) Uani . . 1.000
O O1 0.85598(11) 0.8928(2) 0.39683(17) 0.0220(6) Uani . . 1.000
O O2 0.79876(11) 0.5495(2) 0.34181(17) 0.0223(6) Uani . . 1.000
O O3 0.81253(10) 0.7081(2) 0.54592(15) 0.0209(6) Uani . . 1.000
C C1 0.96902(16) 0.6103(3) 0.5496(2) 0.0214(8) Uani . . 1.000
C C2 1.00375(19) 0.5330(4) 0.6658(3) 0.0312(10) Uani . . 1.000
C C3 1.0834(2) 0.4638(5) 0.7248(4) 0.0393(12) Uani . . 1.000
C C4 1.1311(2) 0.4729(5) 0.6705(3) 0.0388(11) Uani . . 1.000
C C5 1.0978(2) 0.5496(5) 0.5556(4) 0.0423(16) Uani . . 1.000
C C6 1.0164(2) 0.6166(5) 0.4950(3) 0.0326(11) Uani . . 1.000
N N1A 0.81112(15) 1.0554(3) 0.6380(3) 0.0214(8) Uani . . 1.000
N N2A 0.79667(18) 1.3549(4) 0.6207(3) 0.0253(9) Uani . . 1.000
N N3A 0.80233(15) 1.1956(4) 0.4697(2) 0.0259(8) Uani . . 1.000
C C1A 0.80313(16) 1.2018(4) 0.5759(2) 0.0185(8) Uani . . 1.000
N N1B 0.50840(19) 0.4864(5) 0.2386(4) 0.0452(11) Uani . . 1.000
N N2B 0.6296(2) 0.6056(4) 0.4032(3) 0.0391(12) Uani . . 1.000
N N3B 0.6265(2) 0.5171(5) 0.2284(4) 0.0391(11) Uani . . 1.000
C C1B 0.5899(2) 0.5383(4) 0.2899(4) 0.0301(11) Uani . . 1.000
O O1W 0.88312(19) 0.7021(3) 0.7987(2) 0.0416(10) Uani . . 1.000
O O2W 0.99736(15) 0.9183(4) 0.9723(2) 0.0421(8) Uani . . 1.000
H H2 0.97270 0.52800 0.70410 0.0370 Uiso calc R 1.000
H H3 1.10560 0.41020 0.80200 0.0470 Uiso calc R 1.000
H H4 1.18560 0.42720 0.71170 0.0470 Uiso calc R 1.000
H H5 1.12960 0.55670 0.51860 0.0510 Uiso calc R 1.000
H H6 0.99350 0.66650 0.41640 0.0390 Uiso calc R 1.000
H H21 0.737(3) 0.538(7) 0.301(4) 0.042(11) Uiso . . 1.000
H H11A 0.8076(16) 0.956(4) 0.606(3) 0.036(8) Uiso . . 1.000
H H12A 0.823(2) 1.061(4) 0.717(3) 0.043(10) Uiso . . 1.000
H H21A 0.7921(16) 1.368(4) 0.680(3) 0.038(7) Uiso . . 1.000
H H22A 0.7998(16) 1.461(4) 0.585(3) 0.045(8) Uiso . . 1.000
H H31A 0.8017(17) 1.287(4) 0.436(3) 0.035(8) Uiso . . 1.000
H H32A 0.8159(13) 1.093(3) 0.441(2) 0.037(6) Uiso . . 1.000
H H11B 0.486(2) 0.501(5) 0.285(3) 0.048(11) Uiso . . 1.000
H H12B 0.480(2) 0.444(5) 0.166(4) 0.052(12) Uiso . . 1.000
H H21B 0.599(2) 0.613(5) 0.437(4) 0.053(12) Uiso . . 1.000
H H22B 0.683(2) 0.653(4) 0.436(3) 0.055(9) Uiso . . 1.000
H H31B 0.5958(18) 0.495(4) 0.156(3) 0.050(9) Uiso . . 1.000
H H11W 0.8672(19) 0.702(4) 0.714(3) 0.052(9) Uiso . . 1.000
H H12W 0.859(2) 0.610(4) 0.809(3) 0.046(10) Uiso . . 1.000
H H21W 0.960(2) 0.982(5) 0.954(3) 0.046(12) Uiso . . 1.000
H H22W 0.973(2) 0.830(5) 0.950(4) 0.048(12) Uiso . . 1.000
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'
As As 0.0499 2.0058 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 As1 O2 . . . 111.03(9) no
O1 As1 O3 . . . 112.25(9) no
O1 As1 C1 . . . 107.92(11) no
O2 As1 O3 . . . 108.09(10) no
O2 As1 C1 . . . 106.05(10) no
O3 As1 C1 . . . 111.34(10) no
As1 O2 H21 . . . 122(3) no
H11W O1W H12W . . . 107(3) no
H21W O2W H22W . . . 100(4) no
H11A N1A H12A . . . 119(3) no
C1A N1A H11A . . . 121(2) no
C1A N1A H12A . . . 120(2) no
H21A N2A H22A . . . 114(3) no
C1A N2A H21A . . . 126(2) no
C1A N2A H22A . . . 121(2) no
H31A N3A H32A . . . 116(3) no
C1A N3A H32A . . . 123.2(14) no
C1A N3A H31A . . . 119(2) no
C1B N1B H11B . . . 117(2) no
H11B N1B H12B . . . 121(4) no
C1B N1B H12B . . . 122(3) no
C1B N2B H22B . . . 120(2) no
C1B N2B H21B . . . 115(3) no
H21B N2B H22B . . . 125(4) no
C1B N3B H31B . . . 115(3) no
As1 C1 C6 . . . 118.4(2) no
C2 C1 C6 . . . 118.7(3) no
As1 C1 C2 . . . 122.8(3) no
C1 C2 C3 . . . 120.5(4) no
C2 C3 C4 . . . 120.6(4) no
C3 C4 C5 . . . 119.7(4) no
C4 C5 C6 . . . 119.6(4) no
C1 C6 C5 . . . 121.0(3) no
C3 C2 H2 . . . 120.00 no
C1 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 119.00 no
C1 C6 H6 . . . 120.00 no
N2A C1A N3A . . . 120.2(3) no
N1A C1A N2A . . . 119.7(3) no
N1A C1A N3A . . . 120.1(3) no
N2B C1B N3B . . . 122.1(4) no
N1B C1B N2B . . . 118.5(4) no
N1B C1B N3B . . . 119.5(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
As1 O1 . . 1.6781(17) no
As1 O2 . . 1.6921(17) no
As1 O3 . . 1.687(2) no
As1 C1 . . 1.930(3) no
O2 H21 . . 0.99(6) no
O1W H11W . . 0.95(3) no
O1W H12W . . 0.88(3) no
O2W H21W . . 0.78(4) no
O2W H22W . . 0.78(4) no
N1A C1A . . 1.329(4) no
N2A C1A . . 1.332(4) no
N3A C1A . . 1.335(3) no
N1A H12A . . 0.90(3) no
N1A H11A . . 0.85(3) no
N2A H21A . . 0.80(3) no
N2A H22A . . 0.94(3) no
N3A H31A . . 0.82(3) no
N3A H32A . . 0.95(2) no
N1B C1B . . 1.360(6) no
N2B C1B . . 1.320(5) no
N3B C1B . . 1.287(6) no
N1B H11B . . 0.89(4) no
N1B H12B . . 0.85(4) no
N2B H21B . . 0.88(5) no
N2B H22B . . 0.93(4) no
N3B H31B . . 0.80(3) no
C1 C2 . . 1.385(4) no
C1 C6 . . 1.379(5) no
C2 C3 . . 1.369(6) no
C3 C4 . . 1.383(6) no
C4 C5 . . 1.373(5) no
C5 C6 . . 1.388(6) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
As1 H11A 3.16(3) . . no
As1 H11W 3.14(3) . . no
As1 H22A 2.95(3) . 1_545 no
As1 H22B 3.09(4) . . no
As1 H32A 3.09(2) . . no
As1 H12W 3.02(3) . 2_564 no
As1 H21A 3.08(3) . 2_574 no
As1 H21W 3.15(4) . 2_574 no
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
_geom_hbond_publ_flag
O2 H21 N3B . 0.99(6) 1.77(6) 2.753(5) 180(6) yes
N1A H11A O3 . 0.85(3) 2.06(3) 2.903(3) 173(3) yes
N1A H12A O1 2_575 0.90(3) 2.05(3) 2.943(4) 172(3) yes
N2A H21A O2 2_575 0.80(3) 2.08(3) 2.867(4) 167(3) yes
N2A H22A O3 1_565 0.94(3) 2.00(3) 2.925(4) 167(3) yes
N3A H31A O2 1_565 0.82(3) 2.32(3) 3.132(3) 179(5) yes
N3A H32A O1 . 0.95(2) 1.91(2) 2.859(4) 174(2) yes
N1B H11B O2W 4_464 0.89(4) 2.34(3) 3.151(5) 151(3) yes
N2B H21B O2W 4_464 0.88(5) 2.18(5) 3.026(5) 163(4) yes
N2B H22B O3 . 0.93(4) 2.10(4) 3.002(4) 165(3) yes
N3B H31B O2W 3_444 0.80(3) 2.15(3) 2.935(5) 169(4) yes
O1W H11W O3 . 0.95(3) 1.81(3) 2.737(3) 167(4) yes
O1W H12W O2 2_565 0.88(3) 1.85(4) 2.715(4) 168(4) yes
O2W H21W O1 2_575 0.78(4) 1.93(4) 2.701(4) 171(4) yes
O2W H22W O1W . 0.78(4) 2.01(4) 2.673(4) 143(4) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 As1 C1 C2 . . . . 136.3(2) no
O1 As1 C1 C6 . . . . -47.5(2) no
O2 As1 C1 C2 . . . . -104.7(2) no
O2 As1 C1 C6 . . . . 71.6(2) no
O3 As1 C1 C2 . . . . 12.7(2) no
O3 As1 C1 C6 . . . . -171.1(2) no
As1 C1 C2 C3 . . . . 176.0(3) no
C6 C1 C2 C3 . . . . -0.2(5) no
As1 C1 C6 C5 . . . . -177.4(3) no
C2 C1 C6 C5 . . . . -1.0(5) no
C1 C2 C3 C4 . . . . 1.3(5) no
C2 C3 C4 C5 . . . . -1.0(6) no
C3 C4 C5 C6 . . . . -0.3(6) no
C4 C5 C6 C1 . . . . 1.3(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656169
2 PubChem 139079436
