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The cation of the title salt, C13H14N3+·C9H6NO4S-, is found to have a conformation with both phenyl rings lying in syn positions with respect to the unsubstituted N atom. The geometry of the guanidinium unit is close to that expected for a central Csp2 atom. The anions are approximately parallel to the (010) plane. The structure is stabilized by a two-dimensional network of inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605077X/sg2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605077X/sg2104Isup2.hkl
Contains datablock I

CCDC reference: 630463

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.45 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP-Plus (Frenz, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N,N'-Diphenylguanidinium 8-hydroxyquinoline-5-sulfonate top
Crystal data top
C13H14N3+·C9H6NO4SF(000) = 1824
Mr = 436.48Dx = 1.387 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 17 reflections
a = 8.797 (2) Åθ = 10.5–18.4°
b = 16.880 (2) ŵ = 0.19 mm1
c = 28.145 (4) ÅT = 293 K
V = 4179.6 (12) Å3Parallelipiped, colourless
Z = 80.39 × 0.37 × 0.17 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
profile data from ω–2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 021
Tmin = 0.942, Tmax = 0.964l = 036
7311 measured reflections3 standard reflections every 180 min
4800 independent reflections intensity decay: 1.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0647P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4800 reflectionsΔρmax = 0.69 e Å3
282 parametersΔρmin = 0.49 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0009 (2)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.48508 (5)0.23367 (4)0.621739 (18)0.03210 (16)
N11.0785 (2)0.23709 (12)0.60358 (7)0.0382 (4)
C21.0629 (3)0.24031 (16)0.55744 (9)0.0444 (6)
H21.15020.24350.53890.053*
C30.9226 (3)0.23928 (18)0.53450 (8)0.0491 (7)
H30.91780.24130.50150.059*
C40.7928 (3)0.23526 (15)0.56057 (8)0.0391 (5)
H40.69870.23390.54550.047*
C50.6751 (2)0.23175 (14)0.64225 (8)0.0324 (5)
C60.7001 (3)0.22847 (16)0.69012 (8)0.0428 (6)
H60.61720.22770.71060.051*
C70.8475 (3)0.22624 (18)0.70919 (8)0.0483 (7)
H70.86110.22280.74190.058*
C80.9701 (3)0.22913 (16)0.68008 (8)0.0402 (5)
C90.9493 (2)0.23353 (14)0.63001 (7)0.0312 (5)
C100.8013 (2)0.23311 (13)0.61051 (7)0.0290 (4)
O11.11182 (18)0.22840 (14)0.69832 (6)0.0568 (5)
H11.17400.23150.67670.085*
O20.4562 (2)0.16004 (11)0.59902 (8)0.0617 (6)
O30.4744 (2)0.29913 (11)0.58852 (8)0.0587 (5)
O40.3941 (2)0.24867 (16)0.66357 (6)0.0735 (7)
N20.8112 (3)0.05806 (14)0.41111 (9)0.0639 (7)
H2A0.83110.10790.41140.077*
N30.8593 (4)0.06603 (15)0.33198 (9)0.0710 (8)
H3A0.88850.11370.33770.085*
N40.7658 (3)0.05043 (15)0.36342 (9)0.0715 (8)
H4A0.73500.07720.38750.086*
H4B0.76700.07180.33570.086*
C110.8114 (4)0.02332 (17)0.36894 (11)0.0574 (7)
C120.7818 (3)0.02229 (16)0.45607 (10)0.0548 (7)
C130.8553 (4)0.04577 (18)0.46972 (12)0.0656 (8)
H130.92090.07130.44880.079*
C140.8314 (5)0.0762 (2)0.51465 (12)0.0755 (10)
H140.87960.12280.52370.091*
C150.7385 (5)0.0387 (2)0.54566 (13)0.0881 (13)
H150.72310.05970.57580.106*
C160.6672 (6)0.0299 (2)0.53286 (15)0.0995 (14)
H160.60500.05610.55450.119*
C170.6878 (5)0.0602 (2)0.48746 (14)0.0823 (11)
H170.63770.10640.47840.099*
C180.8666 (4)0.04008 (19)0.28378 (12)0.0669 (9)
C190.9501 (5)0.0259 (2)0.27126 (15)0.0815 (11)
H191.00080.05510.29430.098*
C200.9576 (5)0.0480 (2)0.22405 (16)0.0928 (13)
H201.01180.09310.21550.111*
C210.8869 (6)0.0047 (3)0.19019 (15)0.0977 (14)
H210.89240.02000.15850.117*
C220.8073 (6)0.0617 (3)0.20269 (14)0.1021 (14)
H220.76110.09220.17930.122*
C230.7950 (5)0.0837 (2)0.24982 (13)0.0832 (11)
H230.73820.12800.25830.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0215 (2)0.0455 (3)0.0293 (3)0.0012 (2)0.0006 (2)0.0004 (2)
N10.0250 (9)0.0562 (12)0.0333 (10)0.0023 (9)0.0046 (8)0.0009 (9)
C20.0316 (11)0.0683 (17)0.0333 (11)0.0017 (11)0.0113 (9)0.0012 (12)
C30.0414 (13)0.0830 (19)0.0229 (10)0.0032 (13)0.0039 (10)0.0036 (12)
C40.0299 (11)0.0598 (15)0.0277 (10)0.0030 (11)0.0025 (9)0.0008 (11)
C50.0207 (9)0.0475 (12)0.0289 (10)0.0009 (9)0.0008 (8)0.0003 (10)
C60.0251 (10)0.0752 (17)0.0281 (10)0.0022 (11)0.0055 (9)0.0014 (11)
C70.0295 (11)0.092 (2)0.0229 (10)0.0007 (13)0.0005 (9)0.0034 (12)
C80.0259 (10)0.0649 (16)0.0298 (11)0.0012 (11)0.0040 (9)0.0014 (11)
C90.0243 (9)0.0420 (12)0.0275 (10)0.0006 (9)0.0017 (8)0.0008 (9)
C100.0240 (9)0.0365 (11)0.0264 (10)0.0008 (9)0.0009 (8)0.0004 (9)
O10.0222 (8)0.1183 (17)0.0300 (8)0.0038 (9)0.0031 (7)0.0039 (10)
O20.0392 (10)0.0475 (11)0.0985 (16)0.0051 (8)0.0119 (10)0.0187 (11)
O30.0419 (10)0.0525 (11)0.0816 (14)0.0062 (9)0.0091 (10)0.0212 (10)
O40.0252 (9)0.159 (2)0.0360 (10)0.0069 (11)0.0019 (8)0.0097 (12)
N20.091 (2)0.0395 (13)0.0615 (15)0.0110 (13)0.0050 (14)0.0063 (11)
N30.100 (2)0.0478 (14)0.0647 (16)0.0271 (14)0.0016 (16)0.0004 (12)
N40.101 (2)0.0513 (15)0.0624 (15)0.0277 (14)0.0080 (16)0.0025 (13)
C110.0645 (18)0.0472 (16)0.0603 (18)0.0151 (14)0.0081 (15)0.0018 (14)
C120.0672 (19)0.0401 (14)0.0570 (16)0.0079 (14)0.0043 (15)0.0029 (13)
C130.077 (2)0.0533 (18)0.0663 (19)0.0052 (16)0.0019 (17)0.0048 (15)
C140.104 (3)0.0552 (19)0.067 (2)0.0006 (18)0.008 (2)0.0089 (17)
C150.138 (4)0.066 (2)0.061 (2)0.020 (2)0.006 (2)0.0035 (18)
C160.139 (4)0.077 (3)0.083 (3)0.004 (3)0.034 (3)0.011 (2)
C170.107 (3)0.0503 (18)0.089 (3)0.0128 (19)0.011 (2)0.0027 (18)
C180.084 (2)0.0516 (18)0.065 (2)0.0226 (16)0.0057 (18)0.0019 (15)
C190.098 (3)0.064 (2)0.083 (2)0.009 (2)0.005 (2)0.0014 (19)
C200.114 (4)0.072 (2)0.092 (3)0.009 (2)0.027 (3)0.017 (2)
C210.131 (4)0.096 (3)0.066 (2)0.019 (3)0.016 (3)0.012 (2)
C220.140 (4)0.100 (3)0.066 (2)0.005 (3)0.003 (3)0.005 (2)
C230.110 (3)0.068 (2)0.071 (2)0.004 (2)0.011 (2)0.007 (2)
Geometric parameters (Å, º) top
S1—O21.4206 (19)N3—H3A0.8600
S1—O41.4461 (18)N4—C111.317 (4)
S1—O31.4504 (19)N4—H4A0.8600
S1—C51.769 (2)N4—H4B0.8600
N1—C21.307 (3)C12—C171.369 (4)
N1—C91.359 (3)C12—C131.373 (4)
C2—C31.393 (4)C13—C141.381 (4)
C2—H20.9300C13—H130.9300
C3—C41.359 (3)C14—C151.353 (5)
C3—H30.9300C14—H140.9300
C4—C101.408 (3)C15—C161.365 (6)
C4—H40.9300C15—H150.9300
C5—C61.366 (3)C16—C171.389 (5)
C5—C101.425 (3)C16—H160.9300
C6—C71.404 (3)C17—H170.9300
C6—H60.9300C18—C231.361 (5)
C7—C81.355 (3)C18—C191.380 (5)
C7—H70.9300C19—C201.382 (5)
C8—O11.349 (3)C19—H190.9300
C8—C91.423 (3)C20—C211.353 (6)
C9—C101.413 (3)C20—H200.9300
O1—H10.8200C21—C221.368 (6)
N2—C111.324 (4)C21—H210.9300
N2—C121.426 (4)C22—C231.382 (5)
N2—H2A0.8600C22—H220.9300
N3—C111.334 (4)C23—H230.9300
N3—C181.427 (4)
O2—S1—O4114.87 (14)C11—N4—H4B120.0
O2—S1—O3111.40 (13)H4A—N4—H4B120.0
O4—S1—O3110.83 (14)N4—C11—N2121.6 (3)
O2—S1—C5107.44 (11)N4—C11—N3121.0 (3)
O4—S1—C5105.11 (10)N2—C11—N3117.4 (3)
O3—S1—C5106.58 (11)C17—C12—C13119.7 (3)
C2—N1—C9117.2 (2)C17—C12—N2119.0 (3)
N1—C2—C3123.6 (2)C13—C12—N2121.1 (3)
N1—C2—H2118.2C12—C13—C14119.7 (3)
C3—C2—H2118.2C12—C13—H13120.2
C4—C3—C2119.7 (2)C14—C13—H13120.2
C4—C3—H3120.2C15—C14—C13120.6 (3)
C2—C3—H3120.2C15—C14—H14119.7
C3—C4—C10119.7 (2)C13—C14—H14119.7
C3—C4—H4120.1C14—C15—C16120.3 (4)
C10—C4—H4120.1C14—C15—H15119.9
C6—C5—C10119.59 (19)C16—C15—H15119.9
C6—C5—S1118.33 (16)C15—C16—C17119.7 (4)
C10—C5—S1122.08 (16)C15—C16—H16120.1
C5—C6—C7121.8 (2)C17—C16—H16120.1
C5—C6—H6119.1C12—C17—C16120.0 (3)
C7—C6—H6119.1C12—C17—H17120.0
C8—C7—C6120.2 (2)C16—C17—H17120.0
C8—C7—H7119.9C23—C18—C19120.2 (3)
C6—C7—H7119.9C23—C18—N3118.7 (3)
O1—C8—C7120.4 (2)C19—C18—N3121.0 (3)
O1—C8—C9119.7 (2)C18—C19—C20119.3 (4)
C7—C8—C9119.9 (2)C18—C19—H19120.4
N1—C9—C10123.92 (18)C20—C19—H19120.4
N1—C9—C8115.91 (19)C21—C20—C19120.6 (4)
C10—C9—C8120.17 (19)C21—C20—H20119.7
C4—C10—C9115.87 (19)C19—C20—H20119.7
C4—C10—C5125.81 (19)C20—C21—C22119.8 (4)
C9—C10—C5118.32 (18)C20—C21—H21120.1
C8—O1—H1109.5C22—C21—H21120.1
C11—N2—C12127.5 (2)C21—C22—C23120.5 (4)
C11—N2—H2A116.3C21—C22—H22119.8
C12—N2—H2A116.3C23—C22—H22119.8
C11—N3—C18126.1 (3)C18—C23—C22119.5 (4)
C11—N3—H3A116.9C18—C23—H23120.3
C18—N3—H3A116.9C22—C23—H23120.3
C11—N4—H4A120.0
C9—N1—C2—C30.8 (4)S1—C5—C10—C40.7 (3)
N1—C2—C3—C40.4 (5)C6—C5—C10—C92.0 (3)
C2—C3—C4—C100.7 (4)S1—C5—C10—C9178.35 (18)
O2—S1—C5—C6110.6 (2)C12—N2—C11—N47.8 (5)
O4—S1—C5—C612.2 (3)C12—N2—C11—N3172.4 (3)
O3—S1—C5—C6129.9 (2)C18—N3—C11—N40.6 (6)
O2—S1—C5—C1069.1 (2)C18—N3—C11—N2179.2 (3)
O4—S1—C5—C10168.1 (2)C11—N2—C12—C17135.1 (4)
O3—S1—C5—C1050.4 (2)C11—N2—C12—C1350.2 (5)
C10—C5—C6—C70.1 (4)C17—C12—C13—C141.3 (5)
S1—C5—C6—C7179.6 (2)N2—C12—C13—C14175.9 (3)
C5—C6—C7—C81.5 (4)C12—C13—C14—C151.3 (6)
C6—C7—C8—O1178.8 (3)C13—C14—C15—C160.1 (7)
C6—C7—C8—C90.7 (4)C14—C15—C16—C171.4 (7)
C2—N1—C9—C100.0 (4)C13—C12—C17—C160.0 (6)
C2—N1—C9—C8179.3 (2)N2—C12—C17—C16174.8 (4)
O1—C8—C9—N10.3 (4)C15—C16—C17—C121.3 (7)
C7—C8—C9—N1179.3 (2)C11—N3—C18—C23125.4 (4)
O1—C8—C9—C10179.0 (2)C11—N3—C18—C1957.5 (5)
C7—C8—C9—C101.4 (4)C23—C18—C19—C201.3 (6)
C3—C4—C10—C91.4 (4)N3—C18—C19—C20178.4 (3)
C3—C4—C10—C5177.6 (2)C18—C19—C20—C211.5 (6)
N1—C9—C10—C41.1 (3)C19—C20—C21—C220.1 (7)
C8—C9—C10—C4178.2 (2)C20—C21—C22—C231.8 (8)
N1—C9—C10—C5178.0 (2)C19—C18—C23—C220.4 (6)
C8—C9—C10—C52.7 (3)N3—C18—C23—C22176.8 (4)
C6—C5—C10—C4179.0 (3)C21—C22—C23—C181.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.992.691 (2)143
O1—H1···N10.822.222.686 (3)116
N2—H2A···O3ii0.862.012.806 (3)153
N3—H3A···O4ii0.862.323.145 (4)160
N4—H4A···O2iii0.862.222.891 (3)135
C4—H4···O30.932.563.102 (3)117
C6—H6···O40.932.392.815 (3)107
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y, z+1.
 

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