Ammonium 2-(3,4-di-methyl-benzo-yl)benzoate dihydrate.

In the anion of the title compound, NH4 (+)·C16H13O3 (-)·2H2O, the benzene rings are twisted with respect to each other by 73.56 (10)°. In the crystal, extensive N-H⋯O and O-H⋯O hydrogen bonds link the cations, anions and lattice water mol-ecules into a three dimensional supra-molecular structure.

Related literature

For the synthesis of the title compound, see: Elofson et al. (1965 ▶). For related compounds, see: Boon et al. (1986 ▶); Yeung et al. (2002 ▶); Gopalakrishnan et al. (2005 ▶); Qiao et al. (2008 ▶); Gouda et al. (2010 ▶).

Experimental

Crystal data

NH4 +·C16H13O3 −·2H2O

M = 307.34

Triclinic,

a = 7.5039 (15) Å

b = 7.7458 (15) Å

c = 14.439 (3) Å

α = 81.63 (3)°

β = 79.15 (3)°

γ = 78.67 (3)°

V = 803.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku MM007-HF CCD (Saturn 724+) diffractometer

6289 measured reflections

2791 independent reflections

1674 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.01

2791 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalStructure (Rigaku/MSC, 2006 ▶); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, new_global_publ_block. DOI: 10.1107/S1600536813012087/xu5697sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012087/xu5697Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

NH4+·C16H13O3−·2H2O	Z = 2
Mr = 307.34	F(000) = 328
Triclinic, P1	Dx = 1.271 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5039 (15) Å	Cell parameters from 9573 reflections
b = 7.7458 (15) Å	θ = 3.2–25.0°
c = 14.439 (3) Å	µ = 0.09 mm−1
α = 81.63 (3)°	T = 293 K
β = 79.15 (3)°	Block, colorless
γ = 78.67 (3)°	0.20 × 0.18 × 0.15 mm
V = 803.0 (3) Å3

Rigaku MM007-HF CCD (Saturn 724+) diffractometer	1674 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.032
Confocal monochromator	θmax = 25.0°, θmin = 3.2°
ω scans at fixed χ = 45°	h = −8→8
6289 measured reflections	k = −9→8
2791 independent reflections	l = −17→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.0127P] where P = (Fo2 + 2Fc2)/3
2791 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.8894 (3)	0.3453 (3)	0.37419 (13)	0.0384 (5)
C2	1.0501 (3)	0.4382 (2)	0.33412 (13)	0.0358 (5)
C3	1.0619 (3)	0.5954 (3)	0.36741 (15)	0.0481 (6)
H3	0.9645	0.6478	0.4100	0.058*
C4	1.2161 (3)	0.6742 (3)	0.33795 (17)	0.0568 (6)
H4	1.2218	0.7789	0.3608	0.068*
C5	1.3603 (3)	0.5986 (3)	0.27530 (17)	0.0596 (7)
H5	1.4644	0.6514	0.2560	0.071*
C6	1.3514 (3)	0.4435 (3)	0.24053 (16)	0.0502 (6)
H6	1.4501	0.3921	0.1982	0.060*
C7	1.1961 (3)	0.3644 (2)	0.26844 (13)	0.0370 (5)
C8	1.1918 (3)	0.2019 (3)	0.22316 (13)	0.0379 (5)
C9	1.0404 (3)	0.2066 (2)	0.16934 (12)	0.0350 (5)
C10	0.9867 (3)	0.0489 (3)	0.15866 (13)	0.0386 (5)
H10	1.0460	−0.0577	0.1862	0.046*
C11	0.8476 (3)	0.0471 (3)	0.10814 (13)	0.0400 (5)
C12	0.7643 (3)	0.2059 (3)	0.06282 (14)	0.0415 (5)
C13	0.8184 (3)	0.3637 (3)	0.07373 (14)	0.0458 (5)
H13	0.7633	0.4702	0.0441	0.055*
C14	0.9519 (3)	0.3644 (3)	0.12749 (14)	0.0416 (5)
H14	0.9825	0.4712	0.1357	0.050*
C15	0.7866 (3)	−0.1259 (3)	0.10343 (17)	0.0578 (6)
H15A	0.8145	−0.1540	0.0391	0.087*
H15B	0.6563	−0.1148	0.1251	0.087*
H15C	0.8504	−0.2188	0.1431	0.087*
C16	0.6165 (3)	0.2111 (3)	0.00431 (17)	0.0592 (6)
H16A	0.5107	0.1731	0.0444	0.089*
H16B	0.6623	0.1335	−0.0442	0.089*
H16C	0.5823	0.3298	−0.0245	0.089*
N1	0.5486 (2)	0.7384 (2)	0.49120 (13)	0.0498 (5)
H1A	0.6138	0.7907	0.5245	0.060*
H1B	0.6234	0.6452	0.4616	0.060*
H1C	0.4464	0.6937	0.5318	0.060*
H1D	0.5135	0.8306	0.4423	0.060*
O1	1.3187 (2)	0.07641 (19)	0.22420 (10)	0.0517 (4)
O2	0.91984 (18)	0.17891 (17)	0.37486 (9)	0.0428 (4)
O3	0.7384 (2)	0.4340 (2)	0.40630 (12)	0.0634 (5)
O4W	0.7770 (2)	0.9592 (2)	0.53226 (11)	0.0572 (4)
H4WA	0.8648	0.9304	0.5697	0.069*
H4WB	0.8282	1.0201	0.4789	0.069*
O5W	0.6084 (2)	0.0140 (3)	0.33873 (12)	0.0833 (6)
H5WA	0.5287	0.0395	0.3001	0.100*
H5WB	0.6978	0.0708	0.3198	0.100*

	U11	U22	U33	U12	U13	U23
C1	0.0357 (12)	0.0423 (13)	0.0370 (11)	−0.0088 (10)	0.0010 (9)	−0.0099 (9)
C2	0.0341 (11)	0.0372 (11)	0.0374 (10)	−0.0096 (9)	−0.0047 (9)	−0.0054 (9)
C3	0.0511 (14)	0.0460 (13)	0.0494 (13)	−0.0131 (11)	−0.0024 (10)	−0.0137 (10)
C4	0.0656 (17)	0.0513 (14)	0.0617 (15)	−0.0262 (12)	−0.0087 (13)	−0.0142 (12)
C5	0.0577 (16)	0.0622 (17)	0.0661 (15)	−0.0360 (13)	−0.0048 (13)	−0.0033 (12)
C6	0.0406 (13)	0.0568 (14)	0.0533 (13)	−0.0181 (11)	0.0046 (10)	−0.0098 (11)
C7	0.0356 (12)	0.0405 (12)	0.0361 (11)	−0.0122 (9)	−0.0038 (9)	−0.0031 (9)
C8	0.0357 (12)	0.0396 (12)	0.0362 (11)	−0.0091 (10)	0.0038 (9)	−0.0056 (9)
C9	0.0370 (11)	0.0337 (11)	0.0331 (10)	−0.0060 (9)	0.0011 (9)	−0.0089 (9)
C10	0.0433 (12)	0.0311 (11)	0.0389 (11)	−0.0037 (9)	−0.0021 (9)	−0.0056 (9)
C11	0.0442 (12)	0.0364 (12)	0.0392 (11)	−0.0092 (10)	0.0004 (10)	−0.0099 (9)
C12	0.0372 (12)	0.0505 (13)	0.0372 (11)	−0.0090 (10)	−0.0008 (9)	−0.0112 (10)
C13	0.0486 (14)	0.0404 (12)	0.0463 (12)	−0.0035 (10)	−0.0089 (10)	−0.0027 (10)
C14	0.0475 (13)	0.0340 (12)	0.0440 (12)	−0.0088 (10)	−0.0049 (10)	−0.0073 (9)
C15	0.0688 (17)	0.0475 (14)	0.0633 (15)	−0.0197 (12)	−0.0099 (12)	−0.0143 (11)
C16	0.0538 (15)	0.0681 (17)	0.0600 (14)	−0.0092 (12)	−0.0171 (12)	−0.0133 (13)
N1	0.0438 (11)	0.0422 (10)	0.0637 (12)	−0.0110 (8)	0.0008 (9)	−0.0148 (9)
O1	0.0425 (9)	0.0480 (9)	0.0634 (10)	0.0012 (7)	−0.0080 (7)	−0.0155 (8)
O2	0.0434 (9)	0.0356 (8)	0.0480 (8)	−0.0117 (6)	0.0002 (7)	−0.0039 (6)
O3	0.0411 (10)	0.0552 (10)	0.0904 (12)	−0.0113 (8)	0.0169 (8)	−0.0289 (9)
O4W	0.0463 (9)	0.0669 (10)	0.0606 (9)	−0.0221 (8)	−0.0130 (7)	0.0081 (8)
O5W	0.0654 (12)	0.1233 (16)	0.0654 (11)	−0.0396 (12)	−0.0147 (9)	0.0123 (11)

C1—O3	1.249 (2)	C11—C15	1.513 (3)
C1—O2	1.263 (2)	C12—C13	1.399 (3)
C1—C2	1.505 (3)	C12—C16	1.507 (3)
C2—C3	1.396 (2)	C13—C14	1.379 (3)
C2—C7	1.395 (3)	C13—H13	0.9300
C3—C4	1.382 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.367 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.386 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.389 (3)	C16—H16C	0.9600
C6—H6	0.9300	N1—H1A	0.9264
C7—C8	1.509 (3)	N1—H1B	0.9263
C8—O1	1.220 (2)	N1—H1C	0.9630
C8—C9	1.484 (3)	N1—H1D	0.9636
C9—C14	1.385 (3)	O4W—H4WA	0.9042
C9—C10	1.396 (3)	O4W—H4WB	0.9039
C10—C11	1.385 (3)	O5W—H5WA	0.8692
C10—H10	0.9300	O5W—H5WB	0.8542
C11—C12	1.396 (3)
O3—C1—O2	124.36 (19)	C10—C11—C15	119.80 (19)
O3—C1—C2	119.25 (18)	C12—C11—C15	120.91 (18)
O2—C1—C2	116.36 (17)	C11—C12—C13	118.71 (17)
C3—C2—C7	118.41 (18)	C11—C12—C16	121.57 (18)
C3—C2—C1	120.09 (18)	C13—C12—C16	119.7 (2)
C7—C2—C1	121.35 (16)	C14—C13—C12	121.3 (2)
C4—C3—C2	121.0 (2)	C14—C13—H13	119.3
C4—C3—H3	119.5	C12—C13—H13	119.3
C2—C3—H3	119.5	C13—C14—C9	120.21 (17)
C5—C4—C3	120.15 (19)	C13—C14—H14	119.9
C5—C4—H4	119.9	C9—C14—H14	119.9
C3—C4—H4	119.9	C11—C15—H15A	109.5
C4—C5—C6	120.0 (2)	C11—C15—H15B	109.5
C4—C5—H5	120.0	H15A—C15—H15B	109.5
C6—C5—H5	120.0	C11—C15—H15C	109.5
C5—C6—C7	120.4 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.8	H15B—C15—H15C	109.5
C7—C6—H6	119.8	C12—C16—H16A	109.5
C6—C7—C2	119.96 (17)	C12—C16—H16B	109.5
C6—C7—C8	117.37 (18)	H16A—C16—H16B	109.5
C2—C7—C8	122.65 (17)	C12—C16—H16C	109.5
O1—C8—C9	121.17 (16)	H16A—C16—H16C	109.5
O1—C8—C7	120.19 (17)	H16B—C16—H16C	109.5
C9—C8—C7	118.34 (17)	H1A—N1—H1B	111.3
C14—C9—C10	118.58 (17)	H1A—N1—H1C	111.9
C14—C9—C8	121.56 (16)	H1B—N1—H1C	108.1
C10—C9—C8	119.85 (18)	H1A—N1—H1D	103.8
C11—C10—C9	121.76 (19)	H1B—N1—H1D	107.6
C11—C10—H10	119.1	H1C—N1—H1D	114.1
C9—C10—H10	119.1	H4WA—O4W—H4WB	105.6
C10—C11—C12	119.28 (17)	H5WA—O5W—H5WB	111.4
O3—C1—C2—C3	28.0 (3)	C2—C7—C8—C9	57.7 (3)
O2—C1—C2—C3	−150.26 (18)	O1—C8—C9—C14	−147.4 (2)
O3—C1—C2—C7	−156.54 (19)	C7—C8—C9—C14	26.3 (3)
O2—C1—C2—C7	25.2 (3)	O1—C8—C9—C10	31.4 (3)
C7—C2—C3—C4	−1.5 (3)	C7—C8—C9—C10	−154.87 (18)
C1—C2—C3—C4	174.1 (2)	C14—C9—C10—C11	−0.4 (3)
C2—C3—C4—C5	0.0 (3)	C8—C9—C10—C11	−179.27 (17)
C3—C4—C5—C6	0.6 (4)	C9—C10—C11—C12	3.1 (3)
C4—C5—C6—C7	0.4 (3)	C9—C10—C11—C15	−176.39 (18)
C5—C6—C7—C2	−2.0 (3)	C10—C11—C12—C13	−3.0 (3)
C5—C6—C7—C8	176.4 (2)	C15—C11—C12—C13	176.5 (2)
C3—C2—C7—C6	2.5 (3)	C10—C11—C12—C16	178.04 (19)
C1—C2—C7—C6	−173.04 (19)	C15—C11—C12—C16	−2.5 (3)
C3—C2—C7—C8	−175.84 (18)	C11—C12—C13—C14	0.4 (3)
C1—C2—C7—C8	8.6 (3)	C16—C12—C13—C14	179.34 (19)
C6—C7—C8—O1	53.1 (3)	C12—C13—C14—C9	2.3 (3)
C2—C7—C8—O1	−128.6 (2)	C10—C9—C14—C13	−2.3 (3)
C6—C7—C8—C9	−120.7 (2)	C8—C9—C14—C13	176.55 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4W	0.93	1.98	2.836 (2)	152
N1—H1B···O3	0.93	1.90	2.820 (2)	170
N1—H1C···O3i	0.96	1.88	2.823 (3)	167
N1—H1D···O5Wii	0.96	2.03	2.871 (3)	144
N1—H1D···O4Wiii	0.96	2.45	3.067 (3)	121
O4W—H4WA···O2iv	0.90	1.93	2.809 (2)	164
O4W—H4WB···O2ii	0.90	1.91	2.808 (2)	172
O5W—H5WA···O1v	0.87	2.04	2.899 (2)	171
O5W—H5WB···O2	0.85	2.31	3.032 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4W	0.93	1.98	2.836 (2)	152
N1—H1B⋯O3	0.93	1.90	2.820 (2)	170
N1—H1C⋯O3i	0.96	1.88	2.823 (3)	167
N1—H1D⋯O5W ii	0.96	2.03	2.871 (3)	144
N1—H1D⋯O4W iii	0.96	2.45	3.067 (3)	121
O4W—H4WA⋯O2iv	0.90	1.93	2.809 (2)	164
O4W—H4WB⋯O2ii	0.90	1.91	2.808 (2)	172
O5W—H5WA⋯O1v	0.87	2.04	2.899 (2)	171
O5W—H5WB⋯O2	0.85	2.31	3.032 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .