#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218482.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_7218482
loop_
_publ_author_name
'Şerb, Mihaela-Diana'
'Kalf, Irmgard'
'Englert, Ulli'
_publ_section_title
;
 Biguanide and squaric acid as pH-dependent building blocks in crystal
 engineering
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              10631
_journal_paper_doi               10.1039/C4CE01643B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C4 H12 N5, 0.5(C4 O4), H2 O'
_chemical_formula_sum            'C6 H14 N5 O3'
_chemical_formula_weight         204.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.075(2)
_cell_angle_beta                 88.633(3)
_cell_angle_gamma                81.063(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5760(14)
_cell_length_b                   8.3143(15)
_cell_length_c                   8.5662(16)
_cell_measurement_reflns_used    2492
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.67
_cell_volume                     474.58(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5853
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             218
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .420
_refine_diff_density_min         -.355
_refine_diff_density_rms         .046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0376
_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)+(0.0560P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1661
_reflns_number_total             2003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01643b2.cif
_cod_data_source_block           1d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218480--7218488.cif.
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218482
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.14232(15) 0.49071(14) 0.23681(13) 0.0302(3) Uani 1 1 d .
O2 O -0.00731(13) 0.19278(12) 0.15276(12) 0.0203(2) Uani 1 1 d .
C1 C 0.06438(17) 0.49557(18) 0.10726(17) 0.0175(3) Uani 1 1 d .
C2 C -0.00282(17) 0.36074(18) 0.06852(17) 0.0159(3) Uani 1 1 d .
N1 N 0.47977(15) 0.74046(15) 0.11287(14) 0.0187(3) Uani 1 1 d .
N2 N 0.35547(14) 0.81048(15) 0.32734(14) 0.0178(3) Uani 1 1 d .
N3 N 0.20142(18) 0.86873(17) 0.53390(16) 0.0219(3) Uani 1 1 d D
H30 H 0.269(2) 0.951(2) 0.526(2) 0.042(5) Uiso 1 1 d D
H31 H 0.115(2) 0.856(3) 0.604(2) 0.038(5) Uiso 1 1 d D
N4 N 0.21287(16) 0.93718(16) 0.04758(16) 0.0195(3) Uani 1 1 d D
H40 H 0.133(2) 0.999(2) 0.086(2) 0.026(4) Uiso 1 1 d D
H41 H 0.178(2) 0.914(2) -0.036(2) 0.034(5) Uiso 1 1 d D
N5 N 0.07229(18) 0.72624(18) 0.40222(18) 0.0266(3) Uani 1 1 d D
H50 H 0.087(2) 0.666(2) 0.340(2) 0.029(4) Uiso 1 1 d D
H51 H -0.026(2) 0.733(3) 0.457(3) 0.054(6) Uiso 1 1 d D
C3 C 0.6171(2) 0.6019(2) 0.23749(19) 0.0272(4) Uani 1 1 d .
H3C H 0.7253 0.6549 0.2317 0.041 Uiso 1 1 calc R
H3D H 0.6447 0.4997 0.2086 0.041 Uiso 1 1 calc R
H3E H 0.5737 0.5577 0.3562 0.041 Uiso 1 1 calc R
C4 C 0.4909(2) 0.7746(2) -0.06924(18) 0.0243(3) Uani 1 1 d .
H4C H 0.4205 0.6963 -0.0903 0.036 Uiso 1 1 calc R
H4D H 0.6161 0.7474 -0.0934 0.036 Uiso 1 1 calc R
H4E H 0.4437 0.9032 -0.1465 0.036 Uiso 1 1 calc R
C5 C 0.34571(17) 0.82471(17) 0.16484(17) 0.0160(3) Uani 1 1 d .
C6 C 0.20656(18) 0.80547(18) 0.41674(18) 0.0187(3) Uani 1 1 d .
O3 O 0.32983(17) 0.18090(16) 0.50233(16) 0.0373(3) Uani 1 1 d D
H3A H 0.295(3) 0.279(2) 0.408(2) 0.047(6) Uiso 1 1 d D
H3B H 0.427(2) 0.195(3) 0.542(3) 0.059(7) Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C2 134.68(13) . 2_565
O1 C1 C2 135.09(13) . .
C2 C1 C2 90.23(11) 2_565 .
O2 C2 C1 135.45(13) . 2_565
O2 C2 C1 134.78(13) . .
C1 C2 C1 89.77(11) 2_565 .
C5 N1 C3 121.27(12) . .
C5 N1 C4 121.71(12) . .
C3 N1 C4 116.93(11) . .
C6 N2 C5 120.02(11) . .
C6 N3 H30 121.4(12) . .
C6 N3 H31 121.5(12) . .
H30 N3 H31 115.1(18) . .
C5 N4 H40 115.0(10) . .
C5 N4 H41 121.0(12) . .
H40 N4 H41 117.8(16) . .
C6 N5 H50 118.0(11) . .
C6 N5 H51 119.4(14) . .
H50 N5 H51 122.5(18) . .
N1 C3 H3C 109.5 . .
N1 C3 H3D 109.5 . .
H3C C3 H3D 109.5 . .
N1 C3 H3E 109.5 . .
H3C C3 H3E 109.5 . .
H3D C3 H3E 109.5 . .
N1 C4 H4C 109.5 . .
N1 C4 H4D 109.5 . .
H4C C4 H4D 109.5 . .
N1 C4 H4E 109.5 . .
H4C C4 H4E 109.5 . .
H4D C4 H4E 109.5 . .
N1 C5 N4 118.75(12) . .
N1 C5 N2 119.29(12) . .
N4 C5 N2 121.59(12) . .
N3 C6 N5 119.33(13) . .
N3 C6 N2 117.96(13) . .
N5 C6 N2 122.47(12) . .
H3A O3 H3B 107.1(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2511(17) .
O2 C2 1.2542(16) .
C1 C2 1.4640(18) 2_565
C1 C2 1.4657(18) .
C2 C1 1.4639(18) 2_565
N1 C5 1.3267(17) .
N1 C3 1.4544(18) .
N1 C4 1.4564(17) .
N2 C6 1.3436(17) .
N2 C5 1.3454(17) .
N3 C6 1.3248(18) .
N3 H30 0.891(15) .
N3 H31 0.867(14) .
N4 C5 1.3422(17) .
N4 H40 0.885(14) .
N4 H41 0.874(14) .
N5 C6 1.3314(18) .
N5 H50 0.878(14) .
N5 H51 0.880(15) .
C3 H3C 0.9800 .
C3 H3D 0.9800 .
C3 H3E 0.9800 .
C4 H4C 0.9800 .
C4 H4D 0.9800 .
C4 H4E 0.9800 .
O3 H3A 0.857(15) .
O3 H3B 0.867(16) .
