#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/79/2217955.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_2217955
loop_
_publ_author_name
'Portalone, Gustavo'
_publ_section_title
;
 Biguanidinium dichloride
;
_journal_coeditor_code           KP2161
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o683
_journal_paper_doi               10.1107/S1600536808006144
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C2 H9 N5 2+, 2Cl -'
_chemical_formula_moiety         'C2 H9 N5 2+, 2(Cl -)'
_chemical_formula_sum            'C2 H9 Cl2 N5'
_chemical_formula_weight         174.04
_chemical_name_systematic
;
Biguanidinium dichloride
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.6878(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.43693(9)
_cell_length_b                   16.93420(18)
_cell_length_c                   6.65260(8)
_cell_measurement_reflns_used    80724
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.99
_cell_measurement_theta_min      3.20
_cell_volume                     716.841(15)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0052
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            80724
_diffrn_reflns_theta_full        31.99
_diffrn_reflns_theta_max         31.99
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.8860
_exptl_absorpt_correction_T_min  0.8520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.136
_refine_ls_extinction_coef       0.110(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0271
_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)+(0.0293P)²+0.2376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                2349
_reflns_number_total             2456
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2161.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217955
_cod_database_fobs_code          2217955
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_occupancy
Cl Cl1 0.86502(5) -0.053995(15) 0.27026(4) 0.03288(9) Uani d 1
Cl Cl2 0.62775(5) 0.315420(18) 0.37349(5) 0.03605(9) Uani d 1
N N1 0.35152(13) 0.16618(5) 0.32041(15) 0.02556(17) Uani d 1
H H1 0.430(3) 0.2034(10) 0.356(3) 0.039(4) Uiso d 1
N N2 0.00539(15) 0.12772(6) 0.20409(16) 0.02955(19) Uani d 1
H H21 0.025(3) 0.0812(11) 0.243(3) 0.038(4) Uiso d 1
H H22 -0.109(3) 0.1408(11) 0.130(3) 0.048(5) Uiso d 1
N N3 0.09938(18) 0.25798(6) 0.21118(17) 0.0335(2) Uani d 1
H H31 -0.025(3) 0.2708(11) 0.195(3) 0.046(5) Uiso d 1
H H32 0.193(3) 0.2941(11) 0.232(3) 0.044(5) Uiso d 1
N N4 0.38953(17) 0.03968(6) 0.18533(15) 0.0304(2) Uani d 1
H H41 0.461(3) -0.0045(12) 0.196(3) 0.050(5) Uiso d 1
H H42 0.308(3) 0.0513(11) 0.078(3) 0.047(5) Uiso d 1
N N5 0.62338(15) 0.08686(7) 0.45410(16) 0.0324(2) Uani d 1
H H51 0.646(3) 0.1178(11) 0.556(3) 0.044(5) Uiso d 1
H H52 0.711(3) 0.0485(11) 0.440(3) 0.051(5) Uiso d 1
C C1 0.14797(15) 0.18273(5) 0.24248(14) 0.02118(17) Uani d 1
C C2 0.45468(15) 0.09538(6) 0.31785(15) 0.02354(18) Uani 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
Cl1 0.04007(15) 0.02213(13) 0.03406(15) 0.00402(9) -0.00208(10) -0.00296(9)
Cl2 0.03243(14) 0.03940(16) 0.03375(15) -0.01269(10) -0.00333(10) 0.00083(10)
N1 0.0205(4) 0.0213(4) 0.0344(4) -0.0012(3) 0.0024(3) -0.0021(3)
N2 0.0220(4) 0.0256(4) 0.0390(5) -0.0017(3) -0.0020(3) 0.0058(4)
N3 0.0368(5) 0.0215(4) 0.0420(6) 0.0052(4) 0.0055(4) 0.0047(4)
N4 0.0379(5) 0.0269(4) 0.0257(4) 0.0089(4) 0.0022(4) -0.0017(3)
N5 0.0253(4) 0.0399(5) 0.0312(5) 0.0067(4) 0.0010(3) 0.0010(4)
C1 0.0229(4) 0.0203(4) 0.0208(4) 0.0012(3) 0.0047(3) 0.0022(3)
C2 0.0218(4) 0.0261(4) 0.0238(4) 0.0022(3) 0.0068(3) 0.0031(3)
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'
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
C1 N1 C2 127.89(9)
C1 N1 H1 117.6(12)
C2 N1 H1 113.6(12)
C1 N2 H21 122.9(12)
C1 N2 H22 116.6(13)
H21 N2 H22 120.4(17)
C1 N3 H31 118.5(13)
C1 N3 H32 121.3(12)
H31 N3 H32 119.0(17)
C2 N4 H41 116.7(12)
C2 N4 H42 119.7(12)
H41 N4 H42 121.2(17)
C2 N5 H51 120.4(12)
C2 N5 H52 119.2(13)
H51 N5 H52 120.4(17)
N2 C1 N3 120.97(10)
N2 C1 N1 122.31(9)
N3 C1 N1 116.70(9)
N5 C2 N4 122.04(10)
N5 C2 N1 116.03(10)
N4 C2 N1 121.93(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3634(13)
N1 C2 1.3719(13)
N1 H1 0.819(18)
N2 C1 1.3056(13)
N2 H21 0.833(18)
N2 H22 0.852(19)
N3 C1 1.3211(13)
N3 H31 0.823(19)
N3 H32 0.857(19)
N4 C2 1.3156(14)
N4 H41 0.88(2)
N4 H42 0.846(19)
N5 C2 1.3131(14)
N5 H51 0.853(19)
N5 H52 0.874(19)
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 Cl2 . 0.819(18) 2.279(18) 3.0796(9) 166.0(16)
N2 H21 Cl1 1_455 0.833(18) 2.530(18) 3.2557(10) 146.4(15)
N2 H22 Cl2 4_465 0.852(19) 2.34(2) 3.1714(10) 167.1(17)
N3 H31 Cl2 1_455 0.823(19) 2.787(19) 3.5098(12) 147.8(16)
N3 H32 Cl1 2_655 0.857(19) 2.599(19) 3.1933(10) 127.4(15)
N3 H32 Cl2 . 0.857(19) 2.835(19) 3.5454(12) 141.3(15)
N4 H41 Cl1 . 0.88(2) 2.703(19) 3.4178(11) 139.4(16)
N4 H42 Cl1 3_655 0.846(19) 2.412(19) 3.2295(10) 162.8(17)
N5 H51 Cl2 4_566 0.853(19) 2.413(19) 3.2404(12) 163.7(16)
N5 H52 Cl1 . 0.874(19) 2.369(19) 3.1905(11) 156.7(17)
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
C2 N1 C1 N2 19.96(17)
C2 N1 C1 N3 -161.49(10)
C1 N1 C2 N5 -159.12(10)
C1 N1 C2 N4 21.55(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15485445
