Diphenyl­guanidinium hydrogen oxalate

In the crystal structure of the title compound, C₁₃H₁₄N₃⁺·C₂HO₄⁻, each cation is linked to four adjacent anions by inter­molecular N—H...O hydrogen bonds [N...O = 2.870 (4)–2.895 (4) Å], and each anion is also linked to two adjacent anions by O—H...O hydrogen bonds [O...O = 2.526 (3) Å] to form a two-dimensional grid network parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.088
• wR factor = 0.199
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.60
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C14    -   C15    ...       1.54 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Diphenylguanidinium-monohydrogen-oxalate (1/1)

Crystal data

C13H14N3^+·C2HO4^−	F(000) = 632
Mr = 301.30	Dx = 1.361 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1357 reflections
a = 15.315 (7) Å	θ = 2.4–24.4°
b = 5.573 (3) Å	µ = 0.10 mm^−1
c = 17.487 (8) Å	T = 298 K
β = 99.863 (9)°	Rod, colorless
V = 1470.3 (12) Å^3	0.39 × 0.23 × 0.08 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2640 independent reflections
Radiation source: fine-focus sealed tube	2271 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→18
Tmin = 0.962, Tmax = 0.992	k = −6→6
7305 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.199	H-atom parameters constrained
S = 1.32	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 1.2264P] where P = (Fo^2 + 2Fc^2)/3
2640 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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
O1	0.2707 (2)	0.4381 (5)	0.70183 (13)	0.0427 (8)
O2	0.23048 (18)	0.5861 (4)	0.58264 (13)	0.0349 (7)
O3	0.22378 (19)	−0.0012 (4)	0.64109 (13)	0.0349 (7)
H3	0.2191	−0.1296	0.6178	0.052*
O4	0.2633 (2)	0.1325 (4)	0.53217 (13)	0.0443 (8)
N1	0.3223 (2)	0.6653 (6)	0.91722 (16)	0.0337 (8)
H1	0.3118	0.6268	0.9624	0.040*
N2	0.2160 (2)	0.9500 (6)	0.91693 (15)	0.0319 (8)
H2	0.2287	0.9393	0.9667	0.038*
N3	0.2608 (2)	0.8448 (6)	0.80150 (15)	0.0349 (8)
H3C	0.2296	0.9595	0.7780	0.042*
H3B	0.2767	0.7276	0.7749	0.042*
C1	0.4249 (3)	0.3361 (7)	0.9279 (2)	0.0385 (10)
H1A	0.3920	0.2614	0.9611	0.046*
C2	0.5012 (3)	0.2288 (8)	0.9118 (2)	0.0472 (11)
H2A	0.5198	0.0834	0.9352	0.057*
C3	0.5497 (3)	0.3333 (9)	0.8621 (2)	0.0510 (12)
H3A	0.6004	0.2589	0.8511	0.061*
C4	0.5225 (3)	0.5497 (9)	0.8288 (2)	0.0484 (11)
H4	0.5554	0.6225	0.7951	0.058*
C5	0.4473 (3)	0.6599 (8)	0.8445 (2)	0.0395 (10)
H5	0.4296	0.8065	0.8214	0.047*
C6	0.3975 (2)	0.5540 (7)	0.89448 (18)	0.0297 (8)
C7	0.2659 (2)	0.8223 (6)	0.87731 (17)	0.0252 (8)
C8	0.1439 (2)	1.1025 (7)	0.88711 (19)	0.0304 (8)
C9	0.0652 (3)	1.0780 (9)	0.9148 (3)	0.0547 (13)
H9	0.0591	0.9560	0.9498	0.066*
C10	−0.0043 (3)	1.2322 (11)	0.8912 (3)	0.0688 (15)
H10	−0.0569	1.2149	0.9104	0.083*
C11	0.0039 (3)	1.4111 (10)	0.8393 (3)	0.0602 (14)
H11	−0.0428	1.5167	0.8239	0.072*
C12	0.0807 (3)	1.4346 (8)	0.8103 (3)	0.0535 (12)
H12	0.0855	1.5526	0.7736	0.064*
C13	0.1516 (3)	1.2835 (7)	0.8352 (2)	0.0392 (10)
H13	0.2046	1.3044	0.8168	0.047*
C14	0.2490 (2)	0.4187 (6)	0.63134 (18)	0.0231 (8)
C15	0.2458 (2)	0.1651 (6)	0.59625 (17)	0.0226 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.082 (2)	0.0253 (14)	0.0203 (13)	0.0001 (14)	0.0070 (13)	−0.0058 (11)
O2	0.0639 (18)	0.0138 (12)	0.0264 (13)	0.0005 (12)	0.0060 (12)	0.0009 (10)
O3	0.0683 (19)	0.0127 (12)	0.0264 (13)	−0.0054 (13)	0.0163 (12)	−0.0018 (10)
O4	0.093 (2)	0.0201 (14)	0.0255 (13)	0.0043 (14)	0.0259 (14)	−0.0030 (11)
N1	0.049 (2)	0.0324 (18)	0.0228 (14)	0.0076 (15)	0.0158 (14)	0.0072 (14)
N2	0.0446 (19)	0.0355 (18)	0.0155 (13)	0.0071 (15)	0.0050 (13)	−0.0021 (13)
N3	0.056 (2)	0.0297 (18)	0.0194 (14)	0.0103 (15)	0.0065 (14)	−0.0002 (13)
C1	0.051 (3)	0.030 (2)	0.034 (2)	0.0006 (19)	0.0056 (18)	0.0044 (18)
C2	0.054 (3)	0.037 (2)	0.049 (2)	0.013 (2)	0.001 (2)	−0.004 (2)
C3	0.041 (2)	0.059 (3)	0.053 (3)	0.010 (2)	0.007 (2)	−0.014 (2)
C4	0.042 (2)	0.059 (3)	0.047 (2)	−0.002 (2)	0.015 (2)	0.002 (2)
C5	0.045 (2)	0.037 (2)	0.037 (2)	−0.0015 (19)	0.0072 (18)	0.0052 (18)
C6	0.038 (2)	0.028 (2)	0.0215 (17)	−0.0010 (17)	0.0003 (15)	−0.0037 (15)
C7	0.035 (2)	0.0227 (18)	0.0178 (16)	−0.0025 (16)	0.0052 (14)	0.0002 (14)
C8	0.037 (2)	0.030 (2)	0.0233 (17)	0.0009 (17)	0.0030 (15)	−0.0051 (16)
C9	0.055 (3)	0.064 (3)	0.047 (2)	0.010 (2)	0.017 (2)	0.019 (2)
C10	0.040 (3)	0.097 (4)	0.074 (3)	0.017 (3)	0.021 (2)	0.017 (3)
C11	0.049 (3)	0.061 (3)	0.064 (3)	0.018 (2)	−0.008 (2)	0.003 (3)
C12	0.069 (3)	0.037 (3)	0.051 (3)	0.004 (2)	−0.001 (2)	0.009 (2)
C13	0.044 (2)	0.033 (2)	0.039 (2)	0.0005 (19)	0.0049 (18)	0.0011 (18)
C14	0.0302 (19)	0.0191 (18)	0.0216 (17)	−0.0011 (15)	0.0086 (14)	−0.0015 (15)
C15	0.0330 (19)	0.0161 (17)	0.0182 (16)	0.0012 (14)	0.0027 (14)	0.0007 (14)

Geometric parameters (Å, º)

O1—C14	1.225 (4)	C3—C4	1.373 (7)
O2—C14	1.262 (4)	C3—H3A	0.9300
O3—C15	1.295 (4)	C4—C5	1.375 (6)
O3—H3	0.8200	C4—H4	0.9300
O4—C15	1.210 (4)	C5—C6	1.386 (5)
N1—C7	1.338 (4)	C5—H5	0.9300
N1—C6	1.423 (5)	C8—C13	1.375 (5)
N1—H1	0.8600	C8—C9	1.381 (6)
N2—C7	1.324 (4)	C9—C10	1.376 (7)
N2—C8	1.419 (5)	C9—H9	0.9300
N2—H2	0.8600	C10—C11	1.367 (7)
N3—C7	1.321 (4)	C10—H10	0.9300
N3—H3C	0.8600	C11—C12	1.365 (7)
N3—H3B	0.8600	C11—H11	0.9300
C1—C6	1.381 (5)	C12—C13	1.384 (6)
C1—C2	1.383 (6)	C12—H12	0.9300
C1—H1A	0.9300	C13—H13	0.9300
C2—C3	1.367 (6)	C14—C15	1.538 (5)
C2—H2A	0.9300
C15—O3—H3	109.5	N3—C7—N2	122.3 (3)
C7—N1—C6	128.3 (3)	N3—C7—N1	120.5 (3)
C7—N1—H1	115.9	N2—C7—N1	117.2 (3)
C6—N1—H1	115.9	C13—C8—C9	118.8 (4)
C7—N2—C8	127.7 (3)	C13—C8—N2	122.2 (3)
C7—N2—H2	116.1	C9—C8—N2	118.8 (3)
C8—N2—H2	116.1	C10—C9—C8	120.7 (4)
C7—N3—H3C	118.8	C10—C9—H9	119.7
C7—N3—H3B	119.8	C8—C9—H9	119.7
H3C—N3—H3B	119.5	C11—C10—C9	120.0 (4)
C6—C1—C2	120.0 (4)	C11—C10—H10	120.0
C6—C1—H1A	120.0	C9—C10—H10	120.0
C2—C1—H1A	120.0	C12—C11—C10	120.0 (4)
C3—C2—C1	121.0 (4)	C12—C11—H11	120.0
C3—C2—H2A	119.5	C10—C11—H11	120.0
C1—C2—H2A	119.5	C11—C12—C13	120.2 (4)
C2—C3—C4	119.1 (4)	C11—C12—H12	119.9
C2—C3—H3A	120.4	C13—C12—H12	119.9
C4—C3—H3A	120.4	C8—C13—C12	120.2 (4)
C3—C4—C5	120.7 (4)	C8—C13—H13	119.9
C3—C4—H4	119.6	C12—C13—H13	119.9
C5—C4—H4	119.6	O1—C14—O2	127.2 (3)
C4—C5—C6	120.4 (4)	O1—C14—C15	117.9 (3)
C4—C5—H5	119.8	O2—C14—C15	114.9 (3)
C6—C5—H5	119.8	O4—C15—O3	125.1 (3)
C1—C6—C5	118.8 (4)	O4—C15—C14	120.7 (3)
C1—C6—N1	117.8 (3)	O3—C15—C14	114.2 (3)
C5—C6—N1	123.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1	0.86	2.05	2.878 (4)	161
N3—H3C···O3^i	0.86	2.39	2.895 (4)	118
N2—H2···O2^ii	0.86	2.03	2.875 (4)	168
N1—H1···O4^iii	0.86	2.11	2.870 (4)	148
O3—H3···O2^iv	0.82	1.72	2.526 (3)	167

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) x, y−1, z.