#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218480.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_7218480
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 H13 N5, C4 O4, 2(H2 O)'
_chemical_formula_sum            'C8 H17 N5 O6'
_chemical_formula_weight         279.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.809(2)
_cell_length_b                   13.372(2)
_cell_length_c                   7.3552(11)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      21.29
_cell_measurement_theta_min      3.05
_cell_volume                     1259.8(3)
_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 .999
_diffrn_measured_fraction_theta_max .999
_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  0.0838
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14347
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         .230
_refine_diff_density_min         -.170
_refine_diff_density_rms         .045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0459
_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)+(0.0350P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                1985
_reflns_number_total             2607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01643b2.cif
_cod_data_source_block           1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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     P2c-2ac
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               7218480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 1.04045(13) 0.26844(14) 0.3586(3) 0.0218(5) Uani 1 1 d .
O2 O 0.81594(14) 0.16428(14) 0.4198(3) 0.0224(5) Uani 1 1 d .
O3 O 0.70327(13) 0.36561(13) 0.2556(3) 0.0229(5) Uani 1 1 d .
O4 O 0.92958(13) 0.46222(14) 0.1869(3) 0.0183(5) Uani 1 1 d .
C1 C 0.9478(2) 0.2933(2) 0.3309(4) 0.0173(6) Uani 1 1 d .
C2 C 0.84537(19) 0.2467(2) 0.3594(4) 0.0153(6) Uani 1 1 d .
C3 C 0.7945(2) 0.33688(19) 0.2850(4) 0.0173(6) Uani 1 1 d .
C4 C 0.89685(19) 0.3810(2) 0.2546(4) 0.0159(6) Uani 1 1 d .
N1 N 0.53116(16) 0.81705(17) -0.0833(3) 0.0169(5) Uani 1 1 d .
N2 N 0.66565(17) 0.70542(17) -0.0323(3) 0.0163(5) Uani 1 1 d D
H20 H 0.7114(16) 0.7573(14) -0.018(4) 0.010(7) Uiso 1 1 d D
N3 N 0.64300(17) 0.54330(17) 0.0862(3) 0.0161(5) Uani 1 1 d D
H30 H 0.6743(19) 0.4870(16) 0.134(4) 0.024(8) Uiso 1 1 d D
H31 H 0.5746(14) 0.552(2) 0.104(4) 0.028(9) Uiso 1 1 d D
N4 N 0.51024(17) 0.65409(18) -0.1686(3) 0.0172(5) Uani 1 1 d D
H40 H 0.5374(19) 0.5956(14) -0.192(4) 0.018(8) Uiso 1 1 d D
H41 H 0.4410(14) 0.660(2) -0.178(4) 0.020(8) Uiso 1 1 d D
N5 N 0.80543(17) 0.60274(19) 0.0164(4) 0.0182(5) Uani 1 1 d D
H50 H 0.837(2) 0.5482(17) 0.064(4) 0.037(10) Uiso 1 1 d D
H51 H 0.843(2) 0.6489(19) -0.044(4) 0.039(10) Uiso 1 1 d D
C6 C 0.5796(2) 0.8950(2) 0.0279(4) 0.0254(7) Uani 1 1 d .
H6A H 0.6267 0.9351 -0.0477 0.038 Uiso 1 1 calc R
H6B H 0.6194 0.8640 0.1268 0.038 Uiso 1 1 calc R
H6C H 0.5252 0.9382 0.0791 0.038 Uiso 1 1 calc R
C5 C 0.4417(2) 0.8463(2) -0.1949(4) 0.0259(7) Uani 1 1 d .
H5A H 0.3772 0.8221 -0.1382 0.039 Uiso 1 1 calc R
H5B H 0.4487 0.8169 -0.3164 0.039 Uiso 1 1 calc R
H5C H 0.4392 0.9193 -0.2050 0.039 Uiso 1 1 calc R
C7 C 0.5671(2) 0.7252(2) -0.0935(4) 0.0157(6) Uani 1 1 d .
C8 C 0.70398(19) 0.6141(2) 0.0239(4) 0.0157(6) Uani 1 1 d .
O5 O 0.82000(16) 0.83818(17) 0.0445(4) 0.0352(6) Uani 1 1 d D
H150 H 0.817(3) 0.8986(16) 0.068(6) 0.086(17) Uiso 1 1 d D
H151 H 0.881(2) 0.825(3) 0.003(7) 0.108(19) Uiso 1 1 d D
O6 O 0.8039(2) 0.03392(17) 0.1283(4) 0.0382(6) Uani 1 1 d D
H160 H 0.766(3) 0.070(2) 0.057(5) 0.065(13) Uiso 1 1 d D
H161 H 0.812(3) 0.069(2) 0.224(4) 0.052(12) 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
O1 C1 C4 134.7(2)
O1 C1 C2 135.5(2)
C4 C1 C2 89.8(2)
O2 C2 C1 134.2(2)
O2 C2 C3 136.1(2)
C1 C2 C3 89.7(2)
O3 C3 C4 133.8(2)
O3 C3 C2 136.8(2)
C4 C3 C2 89.4(2)
O4 C4 C1 134.0(2)
O4 C4 C3 135.0(2)
C1 C4 C3 91.0(2)
C7 N1 C5 119.5(2)
C7 N1 C6 123.3(2)
C5 N1 C6 117.1(2)
C7 N2 C8 126.8(2)
C7 N2 H20 118.8(15)
C8 N2 H20 114.2(15)
C8 N3 H30 117.6(16)
C8 N3 H31 122.5(19)
H30 N3 H31 119(3)
C7 N4 H40 120.5(18)
C7 N4 H41 121.5(18)
H40 N4 H41 117(2)
C8 N5 H50 122(2)
C8 N5 H51 118(2)
H50 N5 H51 120(3)
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N1 C7 N4 120.3(2)
N1 C7 N2 119.1(2)
N4 C7 N2 120.5(2)
N5 C8 N3 121.5(3)
N5 C8 N2 116.3(3)
N3 C8 N2 122.2(2)
H150 O5 H151 108(4)
H160 O6 H161 106(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.249(3)
O2 C2 1.247(3)
O3 C3 1.248(3)
O4 C4 1.266(3)
C1 C4 1.455(4)
C1 C2 1.467(4)
C2 C3 1.476(4)
C3 C4 1.456(4)
N1 C7 1.313(3)
N1 C5 1.463(3)
N1 C6 1.463(3)
N2 C7 1.366(3)
N2 C8 1.379(3)
N2 H20 0.914(16)
N3 C8 1.310(3)
N3 H30 0.923(17)
N3 H31 0.894(17)
N4 C7 1.319(3)
N4 H40 0.873(17)
N4 H41 0.893(17)
N5 C8 1.309(3)
N5 H50 0.905(17)
N5 H51 0.903(18)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
O5 H150 0.828(19)
O5 H151 0.854(19)
O6 H160 0.864(19)
O6 H161 0.850(18)
