2-(4-Methyl­piperazin-4-ium-1-yl­carbonyl)­benzoate monohydrate

The title compound, C₁₃H₁₆N₂O₃·H₂O, is an intramolecular salt and combines a water molecule via an O—H...O intermolecular hydrogen bond. In the crystal structure, the packing of the molecules is stabilized by O—H...O and N—H...O hydrogen bonds, and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.110
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker 1997); cell refinement: SMART; data reduction: SAINT (Bruker 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-(4-methylpiperazin-4-ium-1-carbonyl)benzoate monohydrate

Crystal data

C13H16N2O3·H2O	F(000) = 568
Mr = 266.29	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 734 reflections
a = 11.494 (6) Å	θ = 2.5–24.9°
b = 12.754 (5) Å	µ = 0.10 mm^−1
c = 10.252 (4) Å	T = 293 K
β = 116.478 (6)°	Prism, colorless
V = 1345.3 (10) Å^3	0.34 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2757 independent reflections
Radiation source: fine-focus sealed tube	1844 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→14
Tmin = 0.965, Tmax = 0.985	k = −15→15
7655 measured reflections	l = −12→12

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.1704P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
2757 reflections	Δρmax = 0.19 e Å^−3
174 parameters	Δρmin = −0.16 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: 0.023 (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
N1	0.47564 (12)	0.48079 (10)	0.22767 (14)	0.0363 (3)
N2	0.22630 (12)	0.41742 (10)	0.01290 (15)	0.0374 (3)
H2	0.2391	0.4318	−0.0667	0.045*
O1	0.59836 (11)	0.59592 (9)	0.40202 (13)	0.0460 (3)
O2	0.72528 (12)	0.52754 (11)	0.20561 (14)	0.0543 (4)
O3	0.91824 (12)	0.45455 (12)	0.27833 (15)	0.0632 (4)
C1	0.46002 (15)	0.38234 (13)	0.14978 (19)	0.0415 (4)
H1A	0.5237	0.3320	0.2125	0.050*
H1B	0.4749	0.3937	0.0648	0.050*
C2	0.32504 (15)	0.33916 (13)	0.10271 (19)	0.0432 (4)
H2A	0.3144	0.2755	0.0467	0.052*
H2B	0.3129	0.3218	0.1880	0.052*
C3	0.24354 (15)	0.51663 (13)	0.09581 (19)	0.0385 (4)
H3A	0.2283	0.5037	0.1802	0.046*
H3B	0.1805	0.5679	0.0347	0.046*
C4	0.37884 (15)	0.55929 (12)	0.14469 (19)	0.0382 (4)
H4A	0.3905	0.5799	0.0602	0.046*
H4B	0.3905	0.6210	0.2046	0.046*
C5	0.09270 (16)	0.37540 (16)	−0.0389 (2)	0.0546 (5)
H5A	0.0749	0.3638	0.0430	0.082*
H5B	0.0854	0.3104	−0.0891	0.082*
H5C	0.0314	0.4249	−0.1040	0.082*
C6	0.58422 (15)	0.50807 (13)	0.34682 (18)	0.0356 (4)
C7	0.68344 (15)	0.42455 (12)	0.42379 (17)	0.0351 (4)
C8	0.79608 (15)	0.41225 (12)	0.40640 (17)	0.0357 (4)
C9	0.88945 (16)	0.34121 (14)	0.49599 (19)	0.0449 (4)
H9	0.9662	0.3337	0.4874	0.054*
C10	0.87048 (18)	0.28183 (15)	0.59711 (19)	0.0510 (5)
H10	0.9339	0.2346	0.6558	0.061*
C11	0.75753 (19)	0.29263 (15)	0.6109 (2)	0.0535 (5)
H11	0.7439	0.2518	0.6780	0.064*
C12	0.66403 (18)	0.36410 (14)	0.52512 (19)	0.0474 (5)
H12	0.5881	0.3717	0.5354	0.057*
C13	0.81701 (16)	0.46983 (13)	0.29007 (18)	0.0394 (4)
O4	0.84020 (12)	0.62888 (11)	0.66502 (14)	0.0618 (4)
H4C	0.7724	0.6122	0.5885	0.093*
H4D	0.9062	0.5963	0.6691	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0292 (7)	0.0313 (7)	0.0423 (8)	0.0037 (6)	0.0104 (6)	−0.0024 (6)
N2	0.0315 (7)	0.0409 (8)	0.0392 (8)	−0.0035 (6)	0.0153 (6)	−0.0003 (6)
O1	0.0402 (7)	0.0362 (7)	0.0540 (8)	0.0002 (5)	0.0142 (6)	−0.0087 (6)
O2	0.0440 (7)	0.0721 (9)	0.0501 (8)	0.0155 (6)	0.0239 (6)	0.0198 (7)
O3	0.0435 (8)	0.0813 (10)	0.0741 (10)	0.0124 (7)	0.0345 (7)	0.0127 (8)
C1	0.0352 (9)	0.0387 (10)	0.0457 (10)	0.0054 (7)	0.0136 (8)	−0.0045 (8)
C2	0.0432 (10)	0.0329 (9)	0.0471 (10)	0.0016 (7)	0.0144 (8)	−0.0005 (8)
C3	0.0331 (9)	0.0387 (9)	0.0438 (10)	0.0048 (7)	0.0171 (7)	0.0022 (8)
C4	0.0342 (9)	0.0330 (9)	0.0439 (10)	0.0032 (7)	0.0144 (8)	0.0035 (7)
C5	0.0371 (10)	0.0608 (12)	0.0619 (12)	−0.0125 (9)	0.0184 (9)	−0.0049 (10)
C6	0.0314 (9)	0.0372 (9)	0.0412 (9)	−0.0004 (7)	0.0188 (7)	0.0004 (8)
C7	0.0331 (9)	0.0338 (9)	0.0330 (9)	0.0016 (7)	0.0100 (7)	−0.0029 (7)
C8	0.0324 (9)	0.0349 (9)	0.0329 (9)	0.0014 (7)	0.0083 (7)	−0.0065 (7)
C9	0.0380 (9)	0.0449 (10)	0.0438 (10)	0.0083 (8)	0.0109 (8)	−0.0050 (9)
C10	0.0553 (11)	0.0436 (10)	0.0395 (10)	0.0135 (9)	0.0081 (9)	0.0033 (9)
C11	0.0684 (13)	0.0469 (11)	0.0432 (11)	0.0053 (10)	0.0231 (10)	0.0094 (9)
C12	0.0498 (11)	0.0495 (11)	0.0460 (10)	0.0039 (9)	0.0241 (9)	0.0045 (9)
C13	0.0342 (9)	0.0420 (10)	0.0401 (10)	−0.0009 (8)	0.0148 (8)	−0.0077 (8)
O4	0.0483 (8)	0.0704 (10)	0.0571 (8)	0.0021 (7)	0.0148 (6)	−0.0122 (7)

Geometric parameters (Å, º)

N1—C6	1.346 (2)	C4—H4B	0.9700
N1—C1	1.456 (2)	C5—H5A	0.9600
N1—C4	1.4561 (19)	C5—H5B	0.9600
N2—C5	1.483 (2)	C5—H5C	0.9600
N2—C2	1.483 (2)	C6—C7	1.502 (2)
N2—C3	1.487 (2)	C7—C12	1.389 (2)
N2—H2	0.9100	C7—C8	1.392 (2)
O1—C6	1.2329 (19)	C8—C9	1.392 (2)
O2—C13	1.261 (2)	C8—C13	1.508 (2)
O3—C13	1.237 (2)	C9—C10	1.377 (3)
C1—C2	1.509 (2)	C9—H9	0.9300
C1—H1A	0.9700	C10—C11	1.374 (3)
C1—H1B	0.9700	C10—H10	0.9300
C2—H2A	0.9700	C11—C12	1.384 (2)
C2—H2B	0.9700	C11—H11	0.9300
C3—C4	1.507 (2)	C12—H12	0.9300
C3—H3A	0.9700	O4—H4C	0.8499
C3—H3B	0.9700	O4—H4D	0.8500
C4—H4A	0.9700
C6—N1—C1	123.96 (13)	H4A—C4—H4B	108.1
C6—N1—C4	120.68 (13)	N2—C5—H5A	109.5
C1—N1—C4	113.42 (13)	N2—C5—H5B	109.5
C5—N2—C2	111.26 (14)	H5A—C5—H5B	109.5
C5—N2—C3	111.39 (13)	N2—C5—H5C	109.5
C2—N2—C3	110.34 (12)	H5A—C5—H5C	109.5
C5—N2—H2	107.9	H5B—C5—H5C	109.5
C2—N2—H2	107.9	O1—C6—N1	122.05 (15)
C3—N2—H2	107.9	O1—C6—C7	119.32 (14)
N1—C1—C2	110.37 (13)	N1—C6—C7	118.24 (14)
N1—C1—H1A	109.6	C12—C7—C8	120.11 (15)
C2—C1—H1A	109.6	C12—C7—C6	116.68 (15)
N1—C1—H1B	109.6	C8—C7—C6	122.98 (15)
C2—C1—H1B	109.6	C9—C8—C7	118.45 (16)
H1A—C1—H1B	108.1	C9—C8—C13	119.39 (15)
N2—C2—C1	110.25 (14)	C7—C8—C13	122.11 (14)
N2—C2—H2A	109.6	C10—C9—C8	121.35 (17)
C1—C2—H2A	109.6	C10—C9—H9	119.3
N2—C2—H2B	109.6	C8—C9—H9	119.3
C1—C2—H2B	109.6	C11—C10—C9	119.74 (17)
H2A—C2—H2B	108.1	C11—C10—H10	120.1
N2—C3—C4	110.61 (13)	C9—C10—H10	120.1
N2—C3—H3A	109.5	C10—C11—C12	120.16 (18)
C4—C3—H3A	109.5	C10—C11—H11	119.9
N2—C3—H3B	109.5	C12—C11—H11	119.9
C4—C3—H3B	109.5	C11—C12—C7	120.15 (18)
H3A—C3—H3B	108.1	C11—C12—H12	119.9
N1—C4—C3	110.64 (13)	C7—C12—H12	119.9
N1—C4—H4A	109.5	O3—C13—O2	124.06 (17)
C3—C4—H4A	109.5	O3—C13—C8	119.25 (15)
N1—C4—H4B	109.5	O2—C13—C8	116.61 (15)
C3—C4—H4B	109.5	H4C—O4—H4D	110.8
C6—N1—C1—C2	139.99 (16)	N1—C6—C7—C8	100.61 (19)
C4—N1—C1—C2	−55.82 (18)	C12—C7—C8—C9	−2.2 (2)
C5—N2—C2—C1	178.09 (15)	C6—C7—C8—C9	172.12 (15)
C3—N2—C2—C1	−57.73 (18)	C12—C7—C8—C13	175.16 (15)
N1—C1—C2—N2	56.35 (19)	C6—C7—C8—C13	−10.5 (2)
C5—N2—C3—C4	−178.78 (14)	C7—C8—C9—C10	1.8 (2)
C2—N2—C3—C4	57.12 (17)	C13—C8—C9—C10	−175.65 (15)
C6—N1—C4—C3	−140.07 (15)	C8—C9—C10—C11	−0.2 (3)
C1—N1—C4—C3	55.16 (18)	C9—C10—C11—C12	−1.0 (3)
N2—C3—C4—N1	−54.97 (18)	C10—C11—C12—C7	0.6 (3)
C1—N1—C6—O1	173.23 (15)	C8—C7—C12—C11	1.1 (3)
C4—N1—C6—O1	10.1 (2)	C6—C7—C12—C11	−173.62 (16)
C1—N1—C6—C7	−14.0 (2)	C9—C8—C13—O3	−1.5 (2)
C4—N1—C6—C7	−177.14 (14)	C7—C8—C13—O3	−178.89 (16)
O1—C6—C7—C12	88.1 (2)	C9—C8—C13—O2	175.15 (15)
N1—C6—C7—C12	−84.87 (19)	C7—C8—C13—O2	−2.2 (2)
O1—C6—C7—C8	−86.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4D···O3^i	0.85	1.95	2.782 (2)	165
O4—H4C···O1	0.85	2.07	2.9139 (19)	171
N2—H2···O3^ii	0.91	2.57	3.149 (2)	123
N2—H2···O2^ii	0.91	1.73	2.633 (2)	173

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