N,N'-Diphenyl­guanidinium 8-hydroxy­quinoline-5-sulfonate

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.

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

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Computing details

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

Crystal data

C13H14N3^+·C9H6NO4S^−	F(000) = 1824
Mr = 436.48	Dx = 1.387 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17 reflections
a = 8.797 (2) Å	θ = 10.5–18.4°
b = 16.880 (2) Å	µ = 0.19 mm^−1
c = 28.145 (4) Å	T = 293 K
V = 4179.6 (12) Å^3	Parallelipiped, colourless
Z = 8	0.39 × 0.37 × 0.17 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
profile data from ω–2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
Tmin = 0.942, Tmax = 0.964	l = 0→36
7311 measured reflections	3 standard reflections every 180 min
4800 independent reflections	intensity decay: 1.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0647P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4800 reflections	Δρmax = 0.69 e Å^−3
282 parameters	Δρmin = −0.49 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48508 (5)	0.23367 (4)	0.621739 (18)	0.03210 (16)
N1	1.0785 (2)	0.23709 (12)	0.60358 (7)	0.0382 (4)
C2	1.0629 (3)	0.24031 (16)	0.55744 (9)	0.0444 (6)
H2	1.1502	0.2435	0.5389	0.053*
C3	0.9226 (3)	0.23928 (18)	0.53450 (8)	0.0491 (7)
H3	0.9178	0.2413	0.5015	0.059*
C4	0.7928 (3)	0.23526 (15)	0.56057 (8)	0.0391 (5)
H4	0.6987	0.2339	0.5455	0.047*
C5	0.6751 (2)	0.23175 (14)	0.64225 (8)	0.0324 (5)
C6	0.7001 (3)	0.22847 (16)	0.69012 (8)	0.0428 (6)
H6	0.6172	0.2277	0.7106	0.051*
C7	0.8475 (3)	0.22624 (18)	0.70919 (8)	0.0483 (7)
H7	0.8611	0.2228	0.7419	0.058*
C8	0.9701 (3)	0.22913 (16)	0.68008 (8)	0.0402 (5)
C9	0.9493 (2)	0.23353 (14)	0.63001 (7)	0.0312 (5)
C10	0.8013 (2)	0.23311 (13)	0.61051 (7)	0.0290 (4)
O1	1.11182 (18)	0.22840 (14)	0.69832 (6)	0.0568 (5)
H1	1.1740	0.2315	0.6767	0.085*
O2	0.4562 (2)	0.16004 (11)	0.59902 (8)	0.0617 (6)
O3	0.4744 (2)	0.29913 (11)	0.58852 (8)	0.0587 (5)
O4	0.3941 (2)	0.24867 (16)	0.66357 (6)	0.0735 (7)
N2	0.8112 (3)	0.05806 (14)	0.41111 (9)	0.0639 (7)
H2A	0.8311	0.1079	0.4114	0.077*
N3	0.8593 (4)	0.06603 (15)	0.33198 (9)	0.0710 (8)
H3A	0.8885	0.1137	0.3377	0.085*
N4	0.7658 (3)	−0.05043 (15)	0.36342 (9)	0.0715 (8)
H4A	0.7350	−0.0772	0.3875	0.086*
H4B	0.7670	−0.0718	0.3357	0.086*
C11	0.8114 (4)	0.02332 (17)	0.36894 (11)	0.0574 (7)
C12	0.7818 (3)	0.02229 (16)	0.45607 (10)	0.0548 (7)
C13	0.8553 (4)	−0.04577 (18)	0.46972 (12)	0.0656 (8)
H13	0.9209	−0.0713	0.4488	0.079*
C14	0.8314 (5)	−0.0762 (2)	0.51465 (12)	0.0755 (10)
H14	0.8796	−0.1228	0.5237	0.091*
C15	0.7385 (5)	−0.0387 (2)	0.54566 (13)	0.0881 (13)
H15	0.7231	−0.0597	0.5758	0.106*
C16	0.6672 (6)	0.0299 (2)	0.53286 (15)	0.0995 (14)
H16	0.6050	0.0561	0.5545	0.119*
C17	0.6878 (5)	0.0602 (2)	0.48746 (14)	0.0823 (11)
H17	0.6377	0.1064	0.4784	0.099*
C18	0.8666 (4)	0.04008 (19)	0.28378 (12)	0.0669 (9)
C19	0.9501 (5)	−0.0259 (2)	0.27126 (15)	0.0815 (11)
H19	1.0008	−0.0551	0.2943	0.098*
C20	0.9576 (5)	−0.0480 (2)	0.22405 (16)	0.0928 (13)
H20	1.0118	−0.0931	0.2155	0.111*
C21	0.8869 (6)	−0.0047 (3)	0.19019 (15)	0.0977 (14)
H21	0.8924	−0.0200	0.1585	0.117*
C22	0.8073 (6)	0.0617 (3)	0.20269 (14)	0.1021 (14)
H22	0.7611	0.0922	0.1793	0.122*
C23	0.7950 (5)	0.0837 (2)	0.24982 (13)	0.0832 (11)
H23	0.7382	0.1280	0.2583	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0215 (2)	0.0455 (3)	0.0293 (3)	0.0012 (2)	−0.0006 (2)	0.0004 (2)
N1	0.0250 (9)	0.0562 (12)	0.0333 (10)	−0.0023 (9)	0.0046 (8)	0.0009 (9)
C2	0.0316 (11)	0.0683 (17)	0.0333 (11)	−0.0017 (11)	0.0113 (9)	0.0012 (12)
C3	0.0414 (13)	0.0830 (19)	0.0229 (10)	0.0032 (13)	0.0039 (10)	0.0036 (12)
C4	0.0299 (11)	0.0598 (15)	0.0277 (10)	0.0030 (11)	−0.0025 (9)	0.0008 (11)
C5	0.0207 (9)	0.0475 (12)	0.0289 (10)	0.0009 (9)	0.0008 (8)	0.0003 (10)
C6	0.0251 (10)	0.0752 (17)	0.0281 (10)	0.0022 (11)	0.0055 (9)	0.0014 (11)
C7	0.0295 (11)	0.092 (2)	0.0229 (10)	−0.0007 (13)	−0.0005 (9)	0.0034 (12)
C8	0.0259 (10)	0.0649 (16)	0.0298 (11)	−0.0012 (11)	−0.0040 (9)	0.0014 (11)
C9	0.0243 (9)	0.0420 (12)	0.0275 (10)	−0.0006 (9)	0.0017 (8)	−0.0008 (9)
C10	0.0240 (9)	0.0365 (11)	0.0264 (10)	0.0008 (9)	0.0009 (8)	0.0004 (9)
O1	0.0222 (8)	0.1183 (17)	0.0300 (8)	−0.0038 (9)	−0.0031 (7)	0.0039 (10)
O2	0.0392 (10)	0.0475 (11)	0.0985 (16)	−0.0051 (8)	−0.0119 (10)	−0.0187 (11)
O3	0.0419 (10)	0.0525 (11)	0.0816 (14)	0.0062 (9)	−0.0091 (10)	0.0212 (10)
O4	0.0252 (9)	0.159 (2)	0.0360 (10)	0.0069 (11)	0.0019 (8)	−0.0097 (12)
N2	0.091 (2)	0.0395 (13)	0.0615 (15)	−0.0110 (13)	−0.0050 (14)	0.0063 (11)
N3	0.100 (2)	0.0478 (14)	0.0647 (16)	−0.0271 (14)	0.0016 (16)	−0.0004 (12)
N4	0.101 (2)	0.0513 (15)	0.0624 (15)	−0.0277 (14)	−0.0080 (16)	0.0025 (13)
C11	0.0645 (18)	0.0472 (16)	0.0603 (18)	−0.0151 (14)	−0.0081 (15)	0.0018 (14)
C12	0.0672 (19)	0.0401 (14)	0.0570 (16)	−0.0079 (14)	−0.0043 (15)	0.0029 (13)
C13	0.077 (2)	0.0533 (18)	0.0663 (19)	0.0052 (16)	0.0019 (17)	0.0048 (15)
C14	0.104 (3)	0.0552 (19)	0.067 (2)	0.0006 (18)	−0.008 (2)	0.0089 (17)
C15	0.138 (4)	0.066 (2)	0.061 (2)	−0.020 (2)	0.006 (2)	0.0035 (18)
C16	0.139 (4)	0.077 (3)	0.083 (3)	0.004 (3)	0.034 (3)	−0.011 (2)
C17	0.107 (3)	0.0503 (18)	0.089 (3)	0.0128 (19)	0.011 (2)	−0.0027 (18)
C18	0.084 (2)	0.0516 (18)	0.065 (2)	−0.0226 (16)	0.0057 (18)	−0.0019 (15)
C19	0.098 (3)	0.064 (2)	0.083 (2)	−0.009 (2)	0.005 (2)	0.0014 (19)
C20	0.114 (4)	0.072 (2)	0.092 (3)	−0.009 (2)	0.027 (3)	−0.017 (2)
C21	0.131 (4)	0.096 (3)	0.066 (2)	−0.019 (3)	0.016 (3)	−0.012 (2)
C22	0.140 (4)	0.100 (3)	0.066 (2)	0.005 (3)	0.003 (3)	0.005 (2)
C23	0.110 (3)	0.068 (2)	0.071 (2)	0.004 (2)	0.011 (2)	0.007 (2)

Geometric parameters (Å, º)

S1—O2	1.4206 (19)	N3—H3A	0.8600
S1—O4	1.4461 (18)	N4—C11	1.317 (4)
S1—O3	1.4504 (19)	N4—H4A	0.8600
S1—C5	1.769 (2)	N4—H4B	0.8600
N1—C2	1.307 (3)	C12—C17	1.369 (4)
N1—C9	1.359 (3)	C12—C13	1.373 (4)
C2—C3	1.393 (4)	C13—C14	1.381 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.359 (3)	C14—C15	1.353 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C10	1.408 (3)	C15—C16	1.365 (6)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.366 (3)	C16—C17	1.389 (5)
C5—C10	1.425 (3)	C16—H16	0.9300
C6—C7	1.404 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—C23	1.361 (5)
C7—C8	1.355 (3)	C18—C19	1.380 (5)
C7—H7	0.9300	C19—C20	1.382 (5)
C8—O1	1.349 (3)	C19—H19	0.9300
C8—C9	1.423 (3)	C20—C21	1.353 (6)
C9—C10	1.413 (3)	C20—H20	0.9300
O1—H1	0.8200	C21—C22	1.368 (6)
N2—C11	1.324 (4)	C21—H21	0.9300
N2—C12	1.426 (4)	C22—C23	1.382 (5)
N2—H2A	0.8600	C22—H22	0.9300
N3—C11	1.334 (4)	C23—H23	0.9300
N3—C18	1.427 (4)
O2—S1—O4	114.87 (14)	C11—N4—H4B	120.0
O2—S1—O3	111.40 (13)	H4A—N4—H4B	120.0
O4—S1—O3	110.83 (14)	N4—C11—N2	121.6 (3)
O2—S1—C5	107.44 (11)	N4—C11—N3	121.0 (3)
O4—S1—C5	105.11 (10)	N2—C11—N3	117.4 (3)
O3—S1—C5	106.58 (11)	C17—C12—C13	119.7 (3)
C2—N1—C9	117.2 (2)	C17—C12—N2	119.0 (3)
N1—C2—C3	123.6 (2)	C13—C12—N2	121.1 (3)
N1—C2—H2	118.2	C12—C13—C14	119.7 (3)
C3—C2—H2	118.2	C12—C13—H13	120.2
C4—C3—C2	119.7 (2)	C14—C13—H13	120.2
C4—C3—H3	120.2	C15—C14—C13	120.6 (3)
C2—C3—H3	120.2	C15—C14—H14	119.7
C3—C4—C10	119.7 (2)	C13—C14—H14	119.7
C3—C4—H4	120.1	C14—C15—C16	120.3 (4)
C10—C4—H4	120.1	C14—C15—H15	119.9
C6—C5—C10	119.59 (19)	C16—C15—H15	119.9
C6—C5—S1	118.33 (16)	C15—C16—C17	119.7 (4)
C10—C5—S1	122.08 (16)	C15—C16—H16	120.1
C5—C6—C7	121.8 (2)	C17—C16—H16	120.1
C5—C6—H6	119.1	C12—C17—C16	120.0 (3)
C7—C6—H6	119.1	C12—C17—H17	120.0
C8—C7—C6	120.2 (2)	C16—C17—H17	120.0
C8—C7—H7	119.9	C23—C18—C19	120.2 (3)
C6—C7—H7	119.9	C23—C18—N3	118.7 (3)
O1—C8—C7	120.4 (2)	C19—C18—N3	121.0 (3)
O1—C8—C9	119.7 (2)	C18—C19—C20	119.3 (4)
C7—C8—C9	119.9 (2)	C18—C19—H19	120.4
N1—C9—C10	123.92 (18)	C20—C19—H19	120.4
N1—C9—C8	115.91 (19)	C21—C20—C19	120.6 (4)
C10—C9—C8	120.17 (19)	C21—C20—H20	119.7
C4—C10—C9	115.87 (19)	C19—C20—H20	119.7
C4—C10—C5	125.81 (19)	C20—C21—C22	119.8 (4)
C9—C10—C5	118.32 (18)	C20—C21—H21	120.1
C8—O1—H1	109.5	C22—C21—H21	120.1
C11—N2—C12	127.5 (2)	C21—C22—C23	120.5 (4)
C11—N2—H2A	116.3	C21—C22—H22	119.8
C12—N2—H2A	116.3	C23—C22—H22	119.8
C11—N3—C18	126.1 (3)	C18—C23—C22	119.5 (4)
C11—N3—H3A	116.9	C18—C23—H23	120.3
C18—N3—H3A	116.9	C22—C23—H23	120.3
C11—N4—H4A	120.0
C9—N1—C2—C3	−0.8 (4)	S1—C5—C10—C4	−0.7 (3)
N1—C2—C3—C4	0.4 (5)	C6—C5—C10—C9	−2.0 (3)
C2—C3—C4—C10	0.7 (4)	S1—C5—C10—C9	178.35 (18)
O2—S1—C5—C6	−110.6 (2)	C12—N2—C11—N4	7.8 (5)
O4—S1—C5—C6	12.2 (3)	C12—N2—C11—N3	−172.4 (3)
O3—S1—C5—C6	129.9 (2)	C18—N3—C11—N4	0.6 (6)
O2—S1—C5—C10	69.1 (2)	C18—N3—C11—N2	−179.2 (3)
O4—S1—C5—C10	−168.1 (2)	C11—N2—C12—C17	−135.1 (4)
O3—S1—C5—C10	−50.4 (2)	C11—N2—C12—C13	50.2 (5)
C10—C5—C6—C7	−0.1 (4)	C17—C12—C13—C14	1.3 (5)
S1—C5—C6—C7	179.6 (2)	N2—C12—C13—C14	175.9 (3)
C5—C6—C7—C8	1.5 (4)	C12—C13—C14—C15	−1.3 (6)
C6—C7—C8—O1	178.8 (3)	C13—C14—C15—C16	−0.1 (7)
C6—C7—C8—C9	−0.7 (4)	C14—C15—C16—C17	1.4 (7)
C2—N1—C9—C10	0.0 (4)	C13—C12—C17—C16	0.0 (6)
C2—N1—C9—C8	179.3 (2)	N2—C12—C17—C16	−174.8 (4)
O1—C8—C9—N1	−0.3 (4)	C15—C16—C17—C12	−1.3 (7)
C7—C8—C9—N1	179.3 (2)	C11—N3—C18—C23	125.4 (4)
O1—C8—C9—C10	179.0 (2)	C11—N3—C18—C19	−57.5 (5)
C7—C8—C9—C10	−1.4 (4)	C23—C18—C19—C20	−1.3 (6)
C3—C4—C10—C9	−1.4 (4)	N3—C18—C19—C20	−178.4 (3)
C3—C4—C10—C5	177.6 (2)	C18—C19—C20—C21	1.5 (6)
N1—C9—C10—C4	1.1 (3)	C19—C20—C21—C22	0.1 (7)
C8—C9—C10—C4	−178.2 (2)	C20—C21—C22—C23	−1.8 (8)
N1—C9—C10—C5	−178.0 (2)	C19—C18—C23—C22	−0.4 (6)
C8—C9—C10—C5	2.7 (3)	N3—C18—C23—C22	176.8 (4)
C6—C5—C10—C4	179.0 (3)	C21—C22—C23—C18	1.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^i	0.82	1.99	2.691 (2)	143
O1—H1···N1	0.82	2.22	2.686 (3)	116
N2—H2A···O3^ii	0.86	2.01	2.806 (3)	153
N3—H3A···O4^ii	0.86	2.32	3.145 (4)	160
N4—H4A···O2^iii	0.86	2.22	2.891 (3)	135
C4—H4···O3	0.93	2.56	3.102 (3)	117
C6—H6···O4	0.93	2.39	2.815 (3)	107

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, −y, −z+1.