#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511256.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_4511256
loop_
_publ_author_name
'Lie, Sharon'
'Maris, Thierry'
'Wuest, James D.'
_publ_section_title
;
 Molecular Networks Created by Charge-Assisted Hydrogen Bonding in
 Phosphonate, Phosphate, and Sulfonate Salts of Bis(amidines)
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3658
_journal_paper_doi               10.1021/cg500726v
_journal_volume                  14
_journal_year                    2014
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C6 H7 O9 P3, C6 H12 N4, C2 H6 O S'
_chemical_formula_sum            'C14 H25 N4 O10 P3 S'
_chemical_formula_weight         534.35
_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                95.688(13)
_cell_angle_beta                 94.235(14)
_cell_angle_gamma                94.317(13)
_cell_formula_units_Z            2
_cell_length_a                   7.513(2)
_cell_length_b                   11.899(3)
_cell_length_c                   12.077(3)
_cell_measurement_reflns_used    2473
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.13
_cell_measurement_theta_min      3.69
_cell_volume                     1067.7(5)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.855
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18830
_diffrn_reflns_theta_full        69.72
_diffrn_reflns_theta_max         69.72
_diffrn_reflns_theta_min         3.69
_exptl_absorpt_coefficient_mu    4.049
_exptl_absorpt_correction_T_max  0.7843
_exptl_absorpt_correction_T_min  0.4601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     237
_refine_ls_restrained_S_all      1.288
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.1244
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3369
_refine_ls_wR_factor_ref         0.3599
_reflns_number_gt                2253
_reflns_number_total             3458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg500726v_si_005.cif
_cod_data_source_block           jw1643
_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/ACS/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4511252--4511257.cif.
;
_cod_original_cell_volume        1067.8(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511256
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2450(13) 0.4113(7) 0.5863(7) 0.0449(19) Uani 1 1 d U A .
C2 C 0.2053(13) 0.5216(7) 0.6210(8) 0.047(2) Uani 1 1 d U . .
H2 H 0.1753 0.5401 0.6953 0.056 Uiso 1 1 calc R . .
C3 C 0.2095(13) 0.6043(7) 0.5474(8) 0.048(2) Uani 1 1 d U . .
C4 C 0.2513(13) 0.5732(8) 0.4377(8) 0.048(2) Uani 1 1 d U . .
H4 H 0.2550 0.6288 0.3865 0.058 Uiso 1 1 calc R . .
C5 C 0.2871(13) 0.4645(8) 0.4027(8) 0.049(2) Uani 1 1 d U . .
C6 C 0.2852(12) 0.3832(8) 0.4770(8) 0.047(2) Uani 1 1 d U . .
H6 H 0.3113 0.3081 0.4533 0.056 Uiso 1 1 calc R . .
O1 O 0.1713(12) 0.1913(6) 0.6176(6) 0.054(2) Uani 0.865(8) 1 d PDU A 1
O2 O 0.4418(11) 0.2922(6) 0.7140(6) 0.058(2) Uani 0.865(8) 1 d PDU A 1
H2O H 0.4914 0.3550 0.7429 0.086 Uiso 0.86 1 calc P A 1
O3 O 0.1466(12) 0.3430(6) 0.7806(6) 0.054(2) Uani 0.865(8) 1 d PDU A 1
O1B O 0.304(7) 0.371(3) 0.796(2) 0.054(7) Uiso 0.135(8) 1 d PDU A 2
H1B H 0.4029 0.4073 0.7917 0.081 Uiso 0.14 1 calc P A 2
O2B O 0.326(6) 0.197(2) 0.641(4) 0.048(6) Uiso 0.135(8) 1 d PDU A 2
O3B O 0.047(3) 0.287(4) 0.705(5) 0.059(7) Uiso 0.135(8) 1 d PDU A 2
O4 O 0.3759(10) 0.8029(5) 0.6364(6) 0.0598(18) Uani 1 1 d U . .
H4A H 0.4332 0.7578 0.6715 0.090 Uiso 1 1 calc . . .
O5 O 0.0665(11) 0.7525(5) 0.6898(6) 0.065(2) Uani 1 1 d U . .
O6 O 0.1316(10) 0.8168(5) 0.5036(6) 0.0604(19) Uani 1 1 d U . .
H6O H 0.0464 0.7806 0.4631 0.091 Uiso 1 1 calc . . .
O7 O 0.3971(11) 0.5203(6) 0.2046(6) 0.066(2) Uani 1 1 d U . .
O8 O 0.1272(10) 0.3887(6) 0.2004(6) 0.0626(19) Uani 1 1 d U . .
H8O H 0.0698 0.3448 0.2378 0.094 Uiso 1 1 calc . . .
O9 O 0.4233(10) 0.3170(5) 0.2533(5) 0.0581(18) Uani 1 1 d U . .
P1 P 0.2440(4) 0.30438(18) 0.68236(19) 0.0465(7) Uani 1 1 d DU . .
P2 P 0.3205(4) 0.4196(2) 0.2585(2) 0.0517(8) Uani 1 1 d U . .
P3 P 0.1862(4) 0.74878(19) 0.5999(2) 0.0516(8) Uani 1 1 d U . .
C7 C 0.0769(14) 0.5419(8) 1.0023(8) 0.049(2) Uani 1 1 d U . .
C8 C 0.3412(16) 0.6288(8) 0.9598(9) 0.061(2) Uani 1 1 d U . .
H8A H 0.3579 0.6646 0.8903 0.073 Uiso 1 1 calc R . .
H8B H 0.4586 0.6085 0.9912 0.073 Uiso 1 1 calc R . .
C9 C 0.2527(16) 0.7077(8) 1.0453(9) 0.059(2) Uani 1 1 d U . .
H9A H 0.3320 0.7274 1.1148 0.071 Uiso 1 1 calc R . .
H9B H 0.2224 0.7782 1.0139 0.071 Uiso 1 1 calc R . .
N1 N 0.2096(12) 0.5286(7) 0.9397(7) 0.0535(19) Uani 1 1 d U . .
H1N H 0.2194 0.4687 0.8923 0.064 Uiso 1 1 calc R . .
N2 N 0.0890(12) 0.6380(7) 1.0661(7) 0.0552(19) Uani 1 1 d U . .
H2N H 0.0117 0.6583 1.1141 0.066 Uiso 1 1 calc R . .
C10 C 0.4272(15) -0.0051(8) 0.4525(9) 0.059(2) Uani 1 1 d U . .
C11 C 0.267(2) -0.0655(10) 0.2905(10) 0.077(3) Uani 1 1 d U . .
H11A H 0.1888 -0.1368 0.2847 0.092 Uiso 1 1 calc R . .
H11B H 0.2968 -0.0488 0.2150 0.092 Uiso 1 1 calc R . .
C12 C 0.185(2) 0.0299(10) 0.3501(11) 0.077(3) Uani 1 1 d U . .
H12A H 0.1865 0.0959 0.3063 0.092 Uiso 1 1 calc R . .
H12B H 0.0601 0.0072 0.3639 0.092 Uiso 1 1 calc R . .
N3 N 0.4258(15) -0.0706(7) 0.3630(8) 0.068(2) Uani 1 1 d U . .
H3N H 0.5120 -0.1142 0.3472 0.081 Uiso 1 1 calc R . .
N4 N 0.2941(13) 0.0563(7) 0.4533(8) 0.061(2) Uani 1 1 d U . .
H4N H 0.2730 0.1066 0.5082 0.074 Uiso 1 1 calc R . .
S1 S 0.3547(12) 0.0626(6) 0.9560(7) 0.093(2) Uani 0.496(9) 1 d PU B 1
O10 O 0.265(2) 0.1782(11) 0.9998(12) 0.149(4) Uani 1 1 d U B 1
C13 C 0.239(3) 0.0057(14) 0.8384(12) 0.114(5) Uani 1 1 d U B 1
H13A H 0.1133 -0.0110 0.8528 0.172 Uiso 1 1 calc R B 1
H13B H 0.2891 -0.0646 0.8114 0.172 Uiso 1 1 calc R B 1
H13C H 0.2456 0.0591 0.7818 0.172 Uiso 1 1 calc R B 1
C14 C 0.207(3) -0.0166(13) 1.0382(15) 0.153(7) Uani 1 1 d U B 1
H14A H 0.1681 0.0348 1.0985 0.229 Uiso 1 1 calc R B 1
H14B H 0.2716 -0.0759 1.0703 0.229 Uiso 1 1 calc R B 1
H14C H 0.1027 -0.0513 0.9903 0.229 Uiso 1 1 calc R B 1
S1B S 0.1446(13) 0.0629(7) 0.9556(7) 0.103(3) Uani 0.504(9) 1 d PU B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . 120.0(8) y
C6 C1 P1 . 119.5(6) y
C2 C1 P1 . 120.5(7) y
C3 C2 C1 . 120.4(9) y
C3 C2 H2 . 119.8 ?
C1 C2 H2 . 119.8 ?
C2 C3 C4 . 118.1(8) y
C2 C3 P3 . 118.9(7) y
C4 C3 P3 . 122.6(6) y
C5 C4 C3 . 121.7(8) y
C5 C4 H4 . 119.1 ?
C3 C4 H4 . 119.1 ?
C4 C5 C6 . 119.7(9) y
C4 C5 P2 . 122.3(7) y
C6 C5 P2 . 117.8(7) y
C5 C6 C1 . 120.0(8) y
C5 C6 H6 . 120.0 ?
C1 C6 H6 . 120.0 ?
P1 O2 H2O . 109.5 ?
P1 O1B H1B . 109.5 ?
P3 O4 H4A . 109.5 ?
P3 O6 H6O . 109.5 ?
P2 O8 H8O . 109.5 ?
O3 P1 O2B . 136.0(17) y
O3 P1 O3B . 49(2) y
O2B P1 O3B . 114(3) y
O3 P1 O1B . 47(2) y
O2B P1 O1B . 122(3) y
O3B P1 O1B . 95(3) y
O3 P1 O2 . 112.4(5) y
O2B P1 O2 . 60.6(19) y
O3B P1 O2 . 150.7(19) y
O1B P1 O2 . 69(2) y
O3 P1 O1 . 116.1(5) y
O2B P1 O1 . 45.2(19) y
O3B P1 O1 . 74(2) y
O1B P1 O1 . 147.6(18) y
O2 P1 O1 . 105.6(5) y
O3 P1 C1 . 109.3(4) y
O2B P1 C1 . 114.5(17) y
O3B P1 C1 . 103.3(19) y
O1B P1 C1 . 104.0(18) y
O2 P1 C1 . 104.6(4) y
O1 P1 C1 . 108.1(4) y
O9 P2 O7 . 117.0(4) y
O9 P2 O8 . 109.9(4) y
O7 P2 O8 . 106.0(4) y
O9 P2 C5 . 109.4(4) y
O7 P2 C5 . 109.0(4) y
O8 P2 C5 . 104.9(4) y
O5 P3 O6 . 114.5(4) y
O5 P3 O4 . 113.5(5) y
O6 P3 O4 . 101.5(4) y
O5 P3 C3 . 110.2(4) y
O6 P3 C3 . 110.0(4) y
O4 P3 C3 . 106.5(4) y
N1 C7 N2 . 114.6(9) y
N1 C7 C7 2_567 122.6(11) y
N2 C7 C7 2_567 122.7(12) y
N1 C8 C9 . 102.5(8) y
N1 C8 H8A . 111.3 ?
C9 C8 H8A . 111.3 ?
N1 C8 H8B . 111.3 ?
C9 C8 H8B . 111.3 ?
H8A C8 H8B . 109.2 ?
N2 C9 C8 . 102.9(8) y
N2 C9 H9A . 111.2 ?
C8 C9 H9A . 111.2 ?
N2 C9 H9B . 111.2 ?
C8 C9 H9B . 111.2 ?
H9A C9 H9B . 109.1 ?
C7 N1 C8 . 110.2(8) y
C7 N1 H1N . 124.9 ?
C8 N1 H1N . 124.9 ?
C7 N2 C9 . 109.7(8) y
C7 N2 H2N . 125.2 ?
C9 N2 H2N . 125.2 ?
N3 C10 N4 . 112.8(11) y
N3 C10 C10 2_656 124.6(12) y
N4 C10 C10 2_656 122.5(13) y
N3 C11 C12 . 100.7(11) y
N3 C11 H11A . 111.6 ?
C12 C11 H11A . 111.6 ?
N3 C11 H11B . 111.6 ?
C12 C11 H11B . 111.6 ?
H11A C11 H11B . 109.4 ?
N4 C12 C11 . 104.9(11) y
N4 C12 H12A . 110.8 ?
C11 C12 H12A . 110.8 ?
N4 C12 H12B . 110.8 ?
C11 C12 H12B . 110.8 ?
H12A C12 H12B . 108.8 ?
C10 N3 C11 . 112.1(10) y
C10 N3 H3N . 123.9 ?
C11 N3 H3N . 123.9 ?
C10 N4 C12 . 108.9(10) y
C10 N4 H4N . 125.5 ?
C12 N4 H4N . 125.5 ?
O10 S1 C13 . 108.2(10) y
O10 S1 C14 . 89.2(9) y
C13 S1 C14 . 90.8(10) y
S1 C13 H13A . 109.5 ?
S1 C13 H13B . 109.5 ?
H13A C13 H13B . 109.5 ?
S1 C13 H13C . 109.5 ?
H13A C13 H13C . 109.5 ?
H13B C13 H13C . 109.5 ?
S1 C14 H14A . 109.5 ?
S1 C14 H14B . 109.5 ?
H14A C14 H14B . 109.5 ?
S1 C14 H14C . 109.5 ?
H14A C14 H14C . 109.5 ?
H14B C14 H14C . 109.5 ?
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
C1 C6 . 1.390(13) y
C1 C2 . 1.398(12) y
C1 P1 . 1.804(8) y
C2 C3 . 1.390(12) y
C2 H2 . 0.9500 ?
C3 C4 . 1.404(14) y
C3 P3 . 1.799(9) y
C4 C5 . 1.372(13) y
C4 H4 . 0.9500 ?
C5 C6 . 1.384(12) y
C5 P2 . 1.811(10) y
C6 H6 . 0.9500 ?
O1 P1 . 1.529(7) y
O2 P1 . 1.528(8) y
O2 H2o . 0.8400 ?
O3 P1 . 1.492(7) y
O1b P1 . 1.528(17) y
O1b H1b . 0.8400 ?
O2b P1 . 1.511(16) y
O3b P1 . 1.527(17) y
O4 P3 . 1.534(8) y
O4 H4a . 0.8400 ?
O5 P3 . 1.459(8) y
O6 P3 . 1.531(7) y
O6 H6o . 0.8400 ?
O7 P2 . 1.516(7) y
O8 P2 . 1.567(8) y
O8 H8o . 0.8400 ?
O9 P2 . 1.491(7) y
C7 N1 . 1.305(13) y
C7 N2 . 1.308(12) y
C7 C7 2_567 1.463(19) y
C8 N1 . 1.479(13) y
C8 C9 . 1.547(15) y
C8 H8a . 0.9900 ?
C8 H8b . 0.9900 ?
C9 N2 . 1.482(14) y
C9 H9a . 0.9900 ?
C9 H9b . 0.9900 ?
N1 H1n . 0.8800 ?
N2 H2n . 0.8800 ?
C10 N3 . 1.267(13) y
C10 N4 . 1.282(13) y
C10 C10 2_656 1.52(2) y
C11 N3 . 1.432(17) y
C11 C12 . 1.482(17) y
C11 H11a . 0.9900 ?
C11 H11b . 0.9900 ?
C12 N4 . 1.432(17) y
C12 H12a . 0.9900 ?
C12 H12b . 0.9900 ?
N3 H3n . 0.8800 ?
N4 H4n . 0.8800 ?
S1 O10 . 1.633(16) y
S1 C13 . 1.665(18) y
S1 C14 . 1.81(2) y
C13 H13a . 0.9800 ?
C13 H13b . 0.9800 ?
C13 H13c . 0.9800 ?
C14 H14a . 0.9800 ?
C14 H14b . 0.9800 ?
C14 H14c . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O O7 0.84 1.69 2.528(11) 176 2_666 y
O1B H1B O7 0.84 1.67 2.51(5) 175.3 2_666 y
O4 H4A O9 0.84 1.71 2.548(10) 170.9 2_666 y
O6 H6O O1 0.84 1.91 2.603(11) 139.1 2_566 y
O6 H6O O3B 0.84 2.15 2.88(5) 145 2_566 y
O8 H8O O5 0.84 1.82 2.657(10) 175.8 2_566 y
N1 H1N O1B 0.88 1.76 2.61(4) 162.4 . y
N1 H1N O3 0.88 1.93 2.768(11) 158.6 . y
N2 H2N O3 0.88 1.8 2.660(11) 163.3 2_567 y
N2 H2N O3B 0.88 2.3 3.09(5) 149.2 2_567 y
N3 H3N O2B 0.88 1.63 2.49(3) 162.6 2_656 y
N3 H3N O2 0.88 2.23 2.975(12) 141.7 2_656 y
N3 H3N O1 0.88 2.63 3.449(14) 154.5 2_656 y
N4 H4N O1 0.88 1.83 2.689(12) 165.1 . y
N4 H4N O2B 0.88 1.85 2.67(4) 155.6 . y
