meso-1,2-Diphenyl­ethyl­enediammonium bis­(hydrogen squarate)

In the title compound, C₁₄H₁₈N₂²⁺·2C₄HO₄⁻, the cation is centrosymmetric. The hydrogen squarate anions form inversion dimers by way of O—H...O links. The cation inter­acts with the anions by way of N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.119
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C11    = ...          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: Program (Reference)?; cell refinement: Program (Reference)?; data reduction: Program (Reference)?; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Program (Reference)?; software used to prepare material for publication: WinGX (Farrugia, 1997).

meso-1,2-Diphenylethylenediammonium bis(hydrogen squarate)

Crystal data

C14H18N2^2+·2C4HO4^−	Z = 1
Mr = 440.4	F(000) = 230
Triclinic, P1	Dx = 1.469 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3817 (6) Å	Cell parameters from 50 reflections
b = 7.3925 (7) Å	θ = 1.8–28.0°
c = 11.5034 (11) Å	µ = 0.11 mm^−1
α = 86.765 (2)°	T = 296 K
β = 80.552 (2)°	Block, colourless
γ = 68.420 (1)°	0.35 × 0.33 × 0.25 mm
V = 497.80 (8) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	Rint = 0.018
ω scans	θmax = 28.0°, θmin = 1.8°
5658 measured reflections	h = −8→8
2276 independent reflections	k = −9→9
2144 reflections with I > 2σ(I)	l = −14→14

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0709P)^2 + 0.1006P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max < 0.001
wR(F^2) = 0.119	Δρmax = 0.28 e Å^−3
S = 1.05	Δρmin = −0.19 e Å^−3
2276 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
148 parameters	Extinction coefficient: 0.15 (2)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.82524 (19)	0.42100 (16)	0.91600 (9)	0.0554 (3)
O2	0.98286 (15)	0.52501 (12)	0.64668 (8)	0.0417 (2)
O3	0.48412 (14)	0.82489 (13)	0.63123 (7)	0.0404 (2)
O4	0.29995 (17)	0.71420 (16)	0.89202 (9)	0.0543 (3)
H4	0.3069	0.6495	0.9525	0.081*
N	1.15803 (15)	0.14803 (13)	0.54710 (8)	0.0296 (2)
H1A	1.1104	0.265	0.5804	0.044*
H1B	1.2448	0.1474	0.478	0.044*
H1C	1.2389	0.059	0.594	0.044*
C1	0.7252 (2)	0.53133 (16)	0.83895 (10)	0.0354 (3)
C2	0.8038 (2)	0.57786 (15)	0.71759 (10)	0.0325 (3)
C3	0.57119 (19)	0.71487 (16)	0.71068 (9)	0.0319 (3)
C4	0.4968 (2)	0.66158 (17)	0.82883 (10)	0.0352 (3)
C5	0.80254 (17)	0.11669 (15)	0.64514 (9)	0.0292 (2)
C6	0.57580 (19)	0.24134 (17)	0.65812 (10)	0.0352 (3)
H6	0.5179	0.316	0.5948	0.042*
C7	0.4354 (2)	0.2544 (2)	0.76585 (12)	0.0443 (3)
H7	0.2831	0.3368	0.7743	0.053*
C8	0.5216 (2)	0.1456 (2)	0.86008 (11)	0.0484 (3)
H8	0.4273	0.1551	0.9321	0.058*
C9	0.7471 (2)	0.0227 (2)	0.84824 (11)	0.0461 (3)
H9	0.8049	−0.0494	0.9124	0.055*
C10	0.8872 (2)	0.00659 (18)	0.74076 (10)	0.0370 (3)
H10	1.0385	−0.0781	0.7325	0.044*
C11	0.95632 (17)	0.10200 (14)	0.52843 (9)	0.0276 (2)
H11	0.8719	0.1978	0.4742	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0598 (6)	0.0618 (6)	0.0406 (5)	−0.0184 (5)	−0.0134 (4)	0.0220 (4)
O2	0.0398 (5)	0.0379 (4)	0.0390 (5)	−0.0087 (4)	0.0037 (4)	0.0022 (3)
O3	0.0376 (5)	0.0446 (5)	0.0325 (4)	−0.0093 (4)	−0.0039 (3)	0.0098 (3)
O4	0.0466 (6)	0.0656 (6)	0.0381 (5)	−0.0135 (5)	0.0089 (4)	0.0081 (4)
N	0.0288 (4)	0.0315 (4)	0.0273 (4)	−0.0118 (3)	0.0001 (3)	0.0008 (3)
C1	0.0403 (6)	0.0343 (5)	0.0306 (5)	−0.0131 (5)	−0.0060 (4)	0.0059 (4)
C2	0.0382 (6)	0.0293 (5)	0.0288 (5)	−0.0122 (4)	−0.0031 (4)	0.0022 (4)
C3	0.0362 (6)	0.0315 (5)	0.0269 (5)	−0.0126 (4)	−0.0020 (4)	0.0022 (4)
C4	0.0379 (6)	0.0365 (6)	0.0283 (5)	−0.0126 (4)	0.0001 (4)	0.0012 (4)
C5	0.0281 (5)	0.0325 (5)	0.0272 (5)	−0.0128 (4)	0.0010 (4)	−0.0032 (4)
C6	0.0293 (5)	0.0386 (6)	0.0363 (6)	−0.0109 (4)	−0.0028 (4)	−0.0056 (4)
C7	0.0294 (6)	0.0525 (7)	0.0471 (7)	−0.0136 (5)	0.0061 (5)	−0.0140 (6)
C8	0.0454 (7)	0.0649 (8)	0.0352 (6)	−0.0270 (6)	0.0122 (5)	−0.0093 (6)
C9	0.0500 (7)	0.0589 (8)	0.0300 (6)	−0.0241 (6)	0.0011 (5)	0.0043 (5)
C10	0.0335 (5)	0.0432 (6)	0.0315 (6)	−0.0130 (5)	−0.0005 (4)	0.0028 (5)
C11	0.0262 (5)	0.0295 (5)	0.0254 (5)	−0.0092 (4)	−0.0024 (4)	0.0015 (4)

Geometric parameters (Å, º)

C1—O1	1.2569 (14)	C5—C10	1.3910 (15)
C2—O2	1.2351 (14)	C5—C11	1.5109 (13)
C3—O3	1.2473 (13)	C6—C7	1.3904 (17)
C4—O4	1.2768 (15)	C6—H6	0.93
O4—H4	0.82	C7—C8	1.377 (2)
N—C11	1.4967 (13)	C7—H7	0.93
N—H1A	0.89	C8—C9	1.380 (2)
N—H1B	0.89	C8—H8	0.93
N—H1C	0.89	C9—C10	1.3849 (16)
C1—C4	1.4410 (17)	C9—H9	0.93
C1—C2	1.4702 (15)	C10—H10	0.93
C2—C3	1.4694 (15)	C11—C11^i	1.5447 (19)
C3—C4	1.4468 (15)	C11—H11	0.98
C5—C6	1.3889 (15)
C4—O4—H4	109.5	C5—C6—C7	119.97 (12)
C11—N—H1A	109.5	C5—C6—H6	120
C11—N—H1B	109.5	C7—C6—H6	120
H1A—N—H1B	109.5	C8—C7—C6	120.07 (12)
C11—N—H1C	109.5	C8—C7—H7	120
H1A—N—H1C	109.5	C6—C7—H7	120
H1B—N—H1C	109.5	C7—C8—C9	120.34 (11)
O1—C1—C4	137.10 (12)	C7—C8—H8	119.8
O1—C1—C2	132.96 (12)	C9—C8—H8	119.8
C4—C1—C2	89.94 (9)	C8—C9—C10	119.95 (12)
O2—C2—C3	133.50 (10)	C8—C9—H9	120
O2—C2—C1	137.36 (11)	C10—C9—H9	120
C3—C2—C1	89.11 (9)	C9—C10—C5	120.24 (11)
O3—C3—C4	137.49 (11)	C9—C10—H10	119.9
O3—C3—C2	132.75 (10)	C5—C10—H10	119.9
C4—C3—C2	89.75 (9)	N—C11—C5	108.92 (8)
O4—C4—C1	137.42 (11)	N—C11—C11^i	108.40 (10)
O4—C4—C3	131.42 (11)	C5—C11—C11^i	113.01 (10)
C1—C4—C3	91.15 (9)	N—C11—H11	108.8
C6—C5—C10	119.42 (10)	C5—C11—H11	108.8
C6—C5—C11	120.28 (10)	C11^i—C11—H11	108.8
C10—C5—C11	120.30 (9)
O1—C1—C2—O2	3.8 (2)	O3—C3—C4—C1	−179.64 (15)
C4—C1—C2—O2	−176.14 (15)	C2—C3—C4—C1	1.82 (9)
O1—C1—C2—C3	−178.27 (14)	C10—C5—C6—C7	−0.34 (17)
C4—C1—C2—C3	1.79 (8)	C11—C5—C6—C7	−179.86 (10)
O2—C2—C3—O3	−2.4 (2)	C5—C6—C7—C8	0.76 (18)
C1—C2—C3—O3	179.56 (13)	C6—C7—C8—C9	−0.2 (2)
O2—C2—C3—C4	176.28 (13)	C7—C8—C9—C10	−0.7 (2)
C1—C2—C3—C4	−1.79 (8)	C8—C9—C10—C5	1.2 (2)
O1—C1—C4—O4	−3.0 (3)	C6—C5—C10—C9	−0.62 (17)
C2—C1—C4—O4	176.88 (16)	C11—C5—C10—C9	178.90 (11)
O1—C1—C4—C3	178.25 (16)	C6—C5—C11—N	123.10 (10)
C2—C1—C4—C3	−1.82 (8)	C10—C5—C11—N	−56.42 (12)
O3—C3—C4—O4	1.5 (2)	C6—C5—C11—C11^i	−116.37 (12)
C2—C3—C4—O4	−177.01 (14)	C10—C5—C11—C11^i	64.12 (15)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1^ii	0.82	1.76	2.5047 (15)	151
N—H1A···O2	0.89	1.94	2.8243 (13)	175
N—H1B···O3^iii	0.89	2.03	2.8663 (13)	155
N—H1C···O3^iv	0.89	1.94	2.7780 (13)	156

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