#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218485.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_7218485
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         'C9 H15 N5, C4 O4, H2 O'
_chemical_formula_sum            'C13 H17 N5 O5'
_chemical_formula_weight         323.32
_chemical_name_systematic
; 
 ? 
;
_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                 102.833(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2558(12)
_cell_length_b                   14.578(2)
_cell_length_c                   13.1414(19)
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      2.53
_cell_volume                     1542.1(4)
_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 1.000
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19615
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .505
_refine_diff_density_min         -.254
_refine_diff_density_rms         .054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0414
_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)+(0.0394P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                2404
_reflns_number_total             3538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01643b2.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7218485
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_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 0.77264(13) 0.04240(8) 0.55531(9) 0.0183(3) Uani 1 1 d .
O2 O 0.42185(14) 0.09423(8) 0.62051(9) 0.0196(3) Uani 1 1 d .
C1 C 0.6220(2) 0.01922(11) 0.52549(12) 0.0152(4) Uani 1 1 d .
C2 C 0.4658(2) 0.04285(11) 0.55494(12) 0.0153(4) Uani 1 1 d .
O3 O 0.95848(16) 0.05798(8) 0.15377(9) 0.0250(3) Uani 1 1 d .
O4 O 1.04073(16) 0.14518(8) -0.05638(9) 0.0267(3) Uani 1 1 d .
C3 C 0.9811(2) 0.02653(11) 0.06920(13) 0.0189(4) Uani 1 1 d .
C4 C 1.0184(2) 0.06569(11) -0.02537(13) 0.0188(4) Uani 1 1 d .
N2 N 0.95859(17) 0.23568(10) 0.19288(11) 0.0165(3) Uani 1 1 d D
H120 H 0.974(2) 0.1763(10) 0.1770(15) 0.035(6) Uiso 1 1 d D
N1 N 0.75668(18) 0.18644(10) 0.27294(12) 0.0212(3) Uani 1 1 d D
H110 H 0.821(2) 0.1401(11) 0.2968(14) 0.033(6) Uiso 1 1 d D
N4 N 0.73861(19) 0.33271(10) 0.20455(12) 0.0227(4) Uani 1 1 d D
H140 H 0.634(2) 0.3399(13) 0.2200(15) 0.035(6) Uiso 1 1 d D
H141 H 0.775(2) 0.3727(12) 0.1627(14) 0.038(6) Uiso 1 1 d D
N3 N 1.13897(19) 0.28929(10) 0.09531(12) 0.0195(3) Uani 1 1 d D
H130 H 1.223(2) 0.3266(13) 0.0893(17) 0.047(7) Uiso 1 1 d D
H131 H 1.101(3) 0.2447(13) 0.0469(15) 0.053(7) Uiso 1 1 d D
N5 N 1.09636(18) 0.37332(10) 0.23523(12) 0.0186(3) Uani 1 1 d D
H150 H 1.065(2) 0.3750(13) 0.2971(13) 0.037(6) Uiso 1 1 d D
H151 H 1.137(2) 0.4239(11) 0.2132(14) 0.024(5) Uiso 1 1 d D
C12 C 0.8145(2) 0.25387(11) 0.22492(13) 0.0171(4) Uani 1 1 d .
C11 C 0.6006(2) 0.18951(12) 0.30403(14) 0.0204(4) Uani 1 1 d .
C6 C 0.4757(2) 0.12928(12) 0.25726(14) 0.0237(4) Uani 1 1 d .
C7 C 0.3278(2) 0.13234(14) 0.29194(15) 0.0302(5) Uani 1 1 d .
H7 H 0.2398 0.0918 0.2623 0.036 Uiso 1 1 calc R
C8 C 0.3070(2) 0.19276(14) 0.36788(16) 0.0324(5) Uani 1 1 d .
H8 H 0.2045 0.1940 0.3894 0.039 Uiso 1 1 calc R
C9 C 0.4322(2) 0.25150(14) 0.41338(16) 0.0334(5) Uani 1 1 d .
H9 H 0.4168 0.2931 0.4661 0.040 Uiso 1 1 calc R
C10 C 0.5806(2) 0.24950(13) 0.38177(15) 0.0288(5) Uani 1 1 d .
H10 H 0.6688 0.2892 0.4133 0.035 Uiso 1 1 calc R
C5 C 0.4971(3) 0.06301(14) 0.17432(16) 0.0394(5) Uani 1 1 d .
H5C H 0.5591 0.0926 0.1278 0.059 Uiso 1 1 calc R
H5D H 0.3878 0.0439 0.1340 0.059 Uiso 1 1 calc R
H5E H 0.5585 0.0091 0.2068 0.059 Uiso 1 1 calc R
C13 C 1.0666(2) 0.30190(11) 0.17351(13) 0.0159(4) Uani 1 1 d .
O5 O 0.91643(17) 0.04298(9) 0.38269(10) 0.0229(3) Uani 1 1 d D
H5A H 0.875(2) 0.0434(14) 0.4354(14) 0.043(7) Uiso 1 1 d D
H5B H 1.019(2) 0.0264(16) 0.3963(17) 0.060(8) 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 133.47(15) . 3_656
O1 C1 C2 135.82(16) . .
C2 C1 C2 90.71(13) 3_656 .
O2 C2 C1 134.11(15) . 3_656
O2 C2 C1 136.60(16) . .
C1 C2 C1 89.29(13) 3_656 .
O3 C3 C4 135.40(16) . .
O3 C3 C4 134.33(16) . 3_755
C4 C3 C4 90.28(13) . 3_755
O4 C4 C3 135.28(16) . .
O4 C4 C3 134.99(16) . 3_755
C3 C4 C3 89.72(13) . 3_755
C12 N2 C13 124.23(14) . .
C12 N2 H120 115.3(12) . .
C13 N2 H120 120.0(12) . .
C12 N1 C11 123.89(15) . .
C12 N1 H110 119.7(13) . .
C11 N1 H110 115.7(13) . .
C12 N4 H140 118.5(12) . .
C12 N4 H141 119.1(12) . .
H140 N4 H141 120.7(17) . .
C13 N3 H130 118.7(14) . .
C13 N3 H131 119.9(14) . .
H130 N3 H131 121.4(19) . .
C13 N5 H150 121.7(12) . .
C13 N5 H151 119.5(12) . .
H150 N5 H151 118.3(17) . .
N4 C12 N1 123.19(16) . .
N4 C12 N2 121.01(15) . .
N1 C12 N2 115.76(15) . .
C10 C11 C6 121.88(17) . .
C10 C11 N1 119.46(16) . .
C6 C11 N1 118.62(16) . .
C11 C6 C7 116.90(18) . .
C11 C6 C5 122.28(17) . .
C7 C6 C5 120.82(18) . .
C8 C7 C6 121.24(19) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C7 C8 C9 120.93(18) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C8 C9 C10 119.29(19) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
C9 C10 C11 119.75(19) . .
C9 C10 H10 120.1 . .
C11 C10 H10 120.1 . .
C6 C5 H5C 109.5 . .
C6 C5 H5D 109.5 . .
H5C C5 H5D 109.5 . .
C6 C5 H5E 109.5 . .
H5C C5 H5E 109.5 . .
H5D C5 H5E 109.5 . .
N5 C13 N3 122.79(16) . .
N5 C13 N2 118.92(15) . .
N3 C13 N2 118.26(15) . .
H5A O5 H5B 113(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2642(19) .
O2 C2 1.2547(19) .
C1 C2 1.456(2) 3_656
C1 C2 1.467(2) .
C2 C1 1.456(2) 3_656
O3 C3 1.2542(19) .
O4 C4 1.2554(19) .
C3 C4 1.461(2) .
C3 C4 1.463(2) 3_755
C4 C3 1.463(2) 3_755
N2 C12 1.373(2) .
N2 C13 1.376(2) .
N2 H120 0.906(14) .
N1 C12 1.314(2) .
N1 C11 1.437(2) .
N1 H110 0.873(14) .
N4 C12 1.308(2) .
N4 H140 0.933(14) .
N4 H141 0.898(14) .
N3 C13 1.311(2) .
N3 H130 0.901(15) .
N3 H131 0.915(15) .
N5 C13 1.309(2) .
N5 H150 0.906(15) .
N5 H151 0.885(14) .
C11 C10 1.382(3) .
C11 C6 1.389(2) .
C6 C7 1.396(2) .
C6 C5 1.496(3) .
C7 C8 1.370(3) .
C7 H7 0.9500 .
C8 C9 1.373(3) .
C8 H8 0.9500 .
C9 C10 1.378(3) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C5 H5C 0.9800 .
C5 H5D 0.9800 .
C5 H5E 0.9800 .
O5 H5A 0.839(15) .
O5 H5B 0.859(16) .
