#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228350.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228350
loop_
_publ_author_name
'Matulková, Irena'
'Císařová, Ivana'
'Němec, Ivan'
_publ_section_title
;
 2-Phenylbiguanidinium hydrogen succinate methanol monosolvate
;
_journal_coeditor_code           HB5725
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3187
_journal_page_last               o3188
_journal_paper_doi               10.1107/S160053681004585X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H12 N5 +, C4 H5 O4 -, C H4 O'
_chemical_formula_moiety         'C4 H5 O4, C8 H12 N5, C H4 O'
_chemical_formula_sum            'C13 H21 N5 O5'
_chemical_formula_weight         327.35
_chemical_name_systematic
;
2-Phenylbiguanidinium hydrogen succinate methanol monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0480(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3280(3)
_cell_length_b                   6.45900(10)
_cell_length_c                   24.6770(6)
_cell_measurement_reflns_used    3693
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      1
_cell_volume                     1642.06(7)
_computing_cell_refinement
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and π scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18123
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.226
_refine_ls_extinction_coef       0.055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1087P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1741
_reflns_number_gt                2613
_reflns_number_total             3568
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5725.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228350
_cod_database_fobs_code          2228350
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.20697(15) -0.1226(2) 0.77926(5) 0.0515(4) Uani d . 1 . .
H H1 0.1757 -0.1468 0.7435 0.062 Uiso d R 1 . .
N N2 0.07708(16) -0.3948(2) 0.79668(5) 0.0570(4) Uani d . 1 . .
H H2A 0.0599 -0.4106 0.7620 0.068 Uiso d R 1 . .
H H2B 0.0280 -0.4630 0.8208 0.068 Uiso d R 1 . .
N N3 0.18707(15) -0.2116(2) 0.86872(5) 0.0514(4) Uani d . 1 . .
N N4 0.16449(16) -0.2862(2) 0.95713(5) 0.0537(4) Uani d . 1 . .
H H4A 0.1524 -0.1453 0.9625 0.064 Uiso d R 1 . .
H H4B 0.1638 -0.3785 0.9874 0.064 Uiso d R 1 . .
N N5 0.18754(16) -0.5585(2) 0.90047(5) 0.0575(4) Uani d . 1 . .
H H5A 0.2005 -0.6075 0.8702 0.069 Uiso d R 1 . .
H H5B 0.1909 -0.6467 0.9288 0.069 Uiso d R 1 . .
C C1 0.15804(17) -0.2481(2) 0.81647(6) 0.0464(4) Uani d . 1 . .
C C2 0.17836(16) -0.3547(2) 0.90737(6) 0.0448(4) Uani d . 1 . .
O O1 -0.16551(14) -0.15632(17) 1.00242(4) 0.0577(4) Uani d . 1 . .
O O2 -0.16362(15) -0.43722(16) 0.95237(5) 0.0616(4) Uani d . 1 . .
H H2 -0.1523 -0.4961 0.9068 0.074 Uiso d R 1 . .
O O3 -0.10001(17) 0.1366(2) 0.81889(5) 0.0738(5) Uani d . 1 . .
O O4 -0.13315(14) 0.42420(17) 0.86173(4) 0.0598(4) Uani d . 1 . .
C C3 0.29311(18) 0.0463(2) 0.78891(6) 0.0519(4) Uani d . 1 . .
C C4 0.3920(2) 0.0464(3) 0.82884(8) 0.0687(6) Uani d . 1 . .
H H4 0.4044 -0.0663 0.8521 0.082 Uiso calc R 1 . .
C C5 0.4738(3) 0.2177(5) 0.83414(11) 0.0929(9) Uani d . 1 . .
H H5 0.5407 0.2191 0.8614 0.112 Uiso calc R 1 . .
C C6 0.4578(3) 0.3832(4) 0.80008(14) 0.0964(10) Uani d . 1 . .
H H6 0.5130 0.4967 0.8042 0.116 Uiso calc R 1 . .
C C7 0.3612(3) 0.3805(4) 0.76041(14) 0.0911(9) Uani d . 1 . .
H H7 0.3508 0.4928 0.7369 0.109 Uiso calc R 1 . .
C C8 0.2768(2) 0.2135(3) 0.75394(9) 0.0694(6) Uani d . 1 . .
H H8 0.2103 0.2139 0.7265 0.083 Uiso calc R 1 . .
C C9 -0.16134(17) -0.2385(2) 0.95785(6) 0.0464(4) Uani d . 1 . .
C C10 -0.15527(19) -0.1185(2) 0.90552(6) 0.0488(4) Uani d . 1 . .
H H10A -0.0830 -0.1701 0.8864 0.059 Uiso calc R 1 . .
H H10B -0.2341 -0.1447 0.8828 0.059 Uiso calc R 1 . .
C C11 -0.13977(19) 0.1122(2) 0.91303(6) 0.0462(4) Uani d . 1 . .
H H11A -0.2155 0.1663 0.9293 0.055 Uiso calc R 1 . .
H H11B -0.0647 0.1387 0.9379 0.055 Uiso calc R 1 . .
C C12 -0.12325(17) 0.2254(2) 0.86057(6) 0.0462(4) Uani 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C3 . . 127.49(14) n
C1 N1 H1 . . 115.0 no
C3 N1 H1 . . 117.4 no
C1 N2 H2A . . 121.6 no
C1 N2 H2B . . 117.6 no
H2A N2 H2B . . 119.8 no
C1 N3 C2 . . 123.36(14) n
C2 N4 H4A . . 119.0 no
C2 N4 H4B . . 121.6 no
H4A N4 H4B . . 119.4 no
C2 N5 H5A . . 120.7 no
C2 N5 H5B . . 121.7 no
H5A N5 H5B . . 117.2 no
N3 C1 N2 . . 125.19(14) n
N3 C1 N1 . . 119.06(15) n
N2 C1 N1 . . 115.64(14) n
N4 C2 N5 . . 117.58(14) n
N4 C2 N3 . . 116.65(14) n
N5 C2 N3 . . 125.71(13) n
C9 O2 H2 . . 114.2 n
C4 C3 C8 . . 119.99(19) no
C4 C3 N1 . . 123.32(16) n
C8 C3 N1 . . 116.63(18) n
C3 C4 C5 . . 119.0(2) no
C3 C4 H4 . . 120.5 no
C5 C4 H4 . . 120.5 no
C6 C5 C4 . . 121.2(3) no
C6 C5 H5 . . 119.4 no
C4 C5 H5 . . 119.4 no
C7 C6 C5 . . 119.3(2) no
C7 C6 H6 . . 120.3 no
C5 C6 H6 . . 120.3 no
C6 C7 C8 . . 121.3(2) no
C6 C7 H7 . . 119.4 no
C8 C7 H7 . . 119.4 no
C3 C8 C7 . . 119.1(2) no
C3 C8 H8 . . 120.4 no
C7 C8 H8 . . 120.4 no
O1 C9 O2 . . 121.57(13) n
O1 C9 C10 . . 123.48(13) n
O2 C9 C10 . . 114.95(13) n
C11 C10 C9 . . 114.32(12) no
C11 C10 H10A . . 108.7 no
C9 C10 H10A . . 108.7 no
C11 C10 H10B . . 108.7 no
C9 C10 H10B . . 108.7 no
H10A C10 H10B . . 107.6 no
C12 C11 C10 . . 113.04(12) no
C12 C11 H11A . . 109.0 no
C10 C11 H11A . . 109.0 no
C12 C11 H11B . . 109.0 no
C10 C11 H11B . . 109.0 no
H11A C11 H11B . . 107.8 no
O3 C12 O4 . . 120.62(13) n
O3 C12 C11 . . 122.59(14) n
O4 C12 C11 . . 116.78(12) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.3495(19) n
N1 C3 . 1.417(2) n
N1 H1 . 0.9313 no
N2 C1 . 1.333(2) n
N2 H2A . 0.8679 no
N2 H2B . 0.9206 no
N3 C1 . 1.3242(19) n
N3 C2 . 1.3358(19) n
N4 C2 . 1.3223(18) n
N4 H4A . 0.9291 no
N4 H4B . 0.9561 no
N5 C2 . 1.331(2) n
N5 H5A . 0.8301 no
N5 H5B . 0.9016 no
O1 C9 . 1.2245(18) n
O2 C9 . 1.2909(19) n
O2 H2 . 1.2016 no
O3 C12 . 1.2164(18) n
O4 C12 . 1.2884(19) n
C3 C4 . 1.368(3) no
C3 C8 . 1.385(2) no
C4 C5 . 1.393(3) no
C4 H4 . 0.9300 no
C5 C6 . 1.363(4) no
C5 H5 . 0.9300 no
C6 C7 . 1.348(5) no
C6 H6 . 0.9300 no
C7 C8 . 1.389(4) no
C7 H7 . 0.9300 no
C8 H8 . 0.9300 no
C9 C10 . 1.511(2) no
C10 C11 . 1.509(2) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
C11 C12 . 1.5069(19) no
C11 H11A . 0.9700 no
C11 H11B . 0.9700 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
N1 H1 O3 2_546 0.93 2.18 3.021(2) 149
N1 H1 O4 2_546 0.93 2.64 3.5217(17) 158
N2 H2A O3 2_546 0.87 2.09 2.8855(17) 152
N2 H2B O4 1_545 0.92 2.14 3.0248(19) 162
N4 H4A O1 3_557 0.93 2.13 3.0273(18) 161
N4 H4B O2 3_547 0.96 1.90 2.8605(16) 180
N5 H5B O1 3_547 0.90 2.15 3.0440(17) 170
O2 H2 O4 1_545 1.20 1.25 2.4500(16) 173
C6 H6 Cg1 2_656 0.93 3.10 3.676(2) 122
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656353
