Morpholin-4-ium hydrogen l-tartrate monohydrate.

In the title compound, C(4)H(10)NO(+)·C(4)H(5)O(6) (-)·H(2)O, the morpholine ring adopts a chair conformation. In the crystal, the tartrate anions are linked via O-H⋯O hydrogen bonds, forming chains propagating along [101]. These chains are linked via N-H⋯O and O-H⋯O hydrogen bonds, involving the morpholinium cation and the water molecule, forming a three-dimensional network.

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010 ▶); Raparti et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related studies on co-crystals of amino derivatives, see: Fu et al. (2010 ▶); Aminabhavi et al. (1986 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C4H10NO+·C4H5O6 −·H2O

M = 255.23

Triclinic,

a = 7.6260 (3) Å

b = 8.2408 (3) Å

c = 10.1674 (4) Å

α = 98.462 (1)°

β = 106.282 (1)°

γ = 104.807 (1)°

V = 576.25 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.968, T max = 0.974

15849 measured reflections

3977 independent reflections

3218 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.05

3977 reflections

182 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055620/lx2207sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055620/lx2207Isup2.hkl

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

C4H10NO+·C4H5O6−·H2O	Z = 2
Mr = 255.23	F(000) = 272
Triclinic, P1	Dx = 1.471 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6260 (3) Å	Cell parameters from 6973 reflections
b = 8.2408 (3) Å	θ = 2.6–31.9°
c = 10.1674 (4) Å	µ = 0.13 mm−1
α = 98.462 (1)°	T = 293 K
β = 106.282 (1)°	Block, colourless
γ = 104.807 (1)°	0.25 × 0.20 × 0.20 mm
V = 576.25 (4) Å3

Bruker Kappa APEXII CCD diffractometer	3977 independent reflections
Radiation source: fine-focus sealed tube	3218 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.0 pixels mm-1	θmax = 32.0°, θmin = 2.2°
ω and φ scan	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −12→12
Tmin = 0.968, Tmax = 0.974	l = −15→15
15849 measured reflections

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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.0699P] where P = (Fo2 + 2Fc2)/3
3977 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.94402 (12)	0.37187 (11)	0.27498 (9)	0.04274 (19)
O2	0.97405 (10)	0.21983 (10)	0.43867 (8)	0.03730 (17)
H2A	1.078 (3)	0.201 (2)	0.4093 (18)	0.070 (5)*
O3	0.64815 (10)	0.44948 (8)	0.32017 (7)	0.02986 (15)
H3A	0.614 (2)	0.529 (2)	0.3718 (16)	0.055 (4)*
O4	0.49940 (9)	0.07745 (8)	0.24744 (7)	0.02624 (14)
H4A	0.435 (2)	0.1291 (19)	0.1931 (16)	0.046 (4)*
O5	0.46940 (10)	0.30910 (9)	0.56376 (7)	0.03325 (16)
O6	0.24385 (10)	0.16066 (12)	0.35901 (9)	0.0434 (2)
O7	0.27079 (16)	0.18179 (14)	0.03248 (8)	0.0589 (3)
N1	0.13637 (14)	0.33402 (11)	−0.18924 (9)	0.03416 (18)
H1A	0.009 (3)	0.299 (2)	−0.2159 (17)	0.058 (4)*
H1B	0.171 (2)	0.406 (2)	−0.2372 (17)	0.054 (4)*
C1	0.89145 (11)	0.31305 (11)	0.36407 (9)	0.02589 (17)
C2	0.72471 (11)	0.34681 (10)	0.40548 (9)	0.02281 (15)
H2	0.7731	0.4103	0.5044	0.027*
C3	0.56984 (11)	0.17709 (10)	0.38751 (8)	0.02054 (15)
H3	0.6295	0.1105	0.4483	0.025*
C4	0.41269 (11)	0.21858 (11)	0.44055 (9)	0.02372 (16)
C5	0.18699 (19)	0.08025 (15)	−0.10810 (11)	0.0423 (2)
H5A	0.0503	0.0270	−0.1283	0.051*
H5B	0.2445	−0.0110	−0.1189	0.051*
C6	0.21726 (18)	0.18979 (14)	−0.20995 (11)	0.0403 (2)
H6A	0.3536	0.2358	−0.1949	0.048*
H6B	0.1544	0.1202	−0.3058	0.048*
C7	0.21262 (16)	0.43291 (14)	−0.04050 (12)	0.0405 (2)
H7A	0.1471	0.5177	−0.0285	0.049*
H7B	0.3487	0.4936	−0.0152	0.049*
C8	0.1826 (2)	0.31178 (19)	0.05380 (12)	0.0536 (3)
H8A	0.2377	0.3759	0.1515	0.064*
H8B	0.0460	0.2582	0.0335	0.064*
O1W	−0.25124 (12)	0.25085 (11)	−0.22673 (10)	0.0442 (2)
H1W	−0.305 (3)	0.152 (3)	−0.2239 (19)	0.066 (5)*
H2W	−0.323 (3)	0.282 (2)	−0.2912 (19)	0.061 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0447 (4)	0.0499 (4)	0.0573 (5)	0.0244 (4)	0.0374 (4)	0.0259 (4)
O2	0.0257 (3)	0.0513 (4)	0.0468 (4)	0.0201 (3)	0.0188 (3)	0.0194 (3)
O3	0.0370 (3)	0.0253 (3)	0.0389 (3)	0.0157 (3)	0.0226 (3)	0.0119 (3)
O4	0.0260 (3)	0.0244 (3)	0.0279 (3)	0.0086 (2)	0.0094 (2)	0.0027 (2)
O5	0.0347 (3)	0.0436 (4)	0.0309 (3)	0.0223 (3)	0.0166 (3)	0.0079 (3)
O6	0.0206 (3)	0.0625 (5)	0.0465 (4)	0.0161 (3)	0.0121 (3)	0.0031 (4)
O7	0.0882 (7)	0.0764 (6)	0.0274 (4)	0.0622 (6)	0.0101 (4)	0.0106 (4)
N1	0.0375 (4)	0.0333 (4)	0.0352 (4)	0.0091 (3)	0.0161 (3)	0.0145 (3)
C1	0.0193 (3)	0.0254 (4)	0.0323 (4)	0.0047 (3)	0.0118 (3)	0.0026 (3)
C2	0.0206 (3)	0.0224 (3)	0.0268 (4)	0.0063 (3)	0.0115 (3)	0.0035 (3)
C3	0.0182 (3)	0.0220 (3)	0.0251 (4)	0.0085 (3)	0.0104 (3)	0.0067 (3)
C4	0.0216 (3)	0.0270 (4)	0.0307 (4)	0.0122 (3)	0.0143 (3)	0.0118 (3)
C5	0.0605 (7)	0.0408 (5)	0.0332 (5)	0.0254 (5)	0.0166 (5)	0.0122 (4)
C6	0.0553 (6)	0.0387 (5)	0.0340 (5)	0.0172 (5)	0.0235 (5)	0.0083 (4)
C7	0.0359 (5)	0.0382 (5)	0.0445 (6)	0.0134 (4)	0.0125 (4)	−0.0005 (4)
C8	0.0798 (9)	0.0697 (8)	0.0315 (5)	0.0532 (7)	0.0212 (5)	0.0137 (5)
O1W	0.0343 (4)	0.0367 (4)	0.0501 (5)	0.0037 (3)	0.0014 (3)	0.0144 (4)

O1—C1	1.2041 (11)	C2—C3	1.5310 (11)
O2—C1	1.3089 (11)	C2—H2	0.9800
O2—H2A	0.958 (19)	C3—C4	1.5367 (11)
O3—C2	1.4119 (10)	C3—H3	0.9800
O3—H3A	0.911 (17)	C5—C6	1.4976 (15)
O4—C3	1.4115 (10)	C5—H5A	0.9700
O4—H4A	0.868 (16)	C5—H5B	0.9700
O5—C4	1.2526 (11)	C6—H6A	0.9700
O6—C4	1.2425 (11)	C6—H6B	0.9700
O7—C5	1.4192 (14)	C7—C8	1.5019 (18)
O7—C8	1.4239 (14)	C7—H7A	0.9700
N1—C7	1.4803 (14)	C7—H7B	0.9700
N1—C6	1.4872 (14)	C8—H8A	0.9700
N1—H1A	0.888 (18)	C8—H8B	0.9700
N1—H1B	0.856 (17)	O1W—H1W	0.825 (19)
C1—C2	1.5224 (11)	O1W—H2W	0.848 (19)
C1—O2—H2A	110.4 (11)	O5—C4—C3	115.75 (7)
C2—O3—H3A	110.2 (10)	O7—C5—C6	110.47 (10)
C3—O4—H4A	109.1 (10)	O7—C5—H5A	109.6
C5—O7—C8	110.99 (9)	C6—C5—H5A	109.6
C7—N1—C6	111.80 (8)	O7—C5—H5B	109.6
C7—N1—H1A	108.3 (11)	C6—C5—H5B	109.6
C6—N1—H1A	113.0 (11)	H5A—C5—H5B	108.1
C7—N1—H1B	106.1 (10)	N1—C6—C5	109.55 (8)
C6—N1—H1B	109.1 (11)	N1—C6—H6A	109.8
H1A—N1—H1B	108.3 (15)	C5—C6—H6A	109.8
O1—C1—O2	124.30 (8)	N1—C6—H6B	109.8
O1—C1—C2	122.71 (8)	C5—C6—H6B	109.8
O2—C1—C2	112.95 (7)	H6A—C6—H6B	108.2
O3—C2—C1	108.22 (7)	N1—C7—C8	109.64 (9)
O3—C2—C3	110.63 (6)	N1—C7—H7A	109.7
C1—C2—C3	110.96 (6)	C8—C7—H7A	109.7
O3—C2—H2	109.0	N1—C7—H7B	109.7
C1—C2—H2	109.0	C8—C7—H7B	109.7
C3—C2—H2	109.0	H7A—C7—H7B	108.2
O4—C3—C2	111.41 (6)	O7—C8—C7	110.28 (10)
O4—C3—C4	113.65 (6)	O7—C8—H8A	109.6
C2—C3—C4	108.61 (6)	C7—C8—H8A	109.6
O4—C3—H3	107.6	O7—C8—H8B	109.6
C2—C3—H3	107.6	C7—C8—H8B	109.6
C4—C3—H3	107.6	H8A—C8—H8B	108.1
O6—C4—O5	126.30 (8)	H1W—O1W—H2W	110.3 (17)
O6—C4—C3	117.95 (8)
O1—C1—C2—O3	1.65 (12)	C2—C3—C4—O6	125.59 (9)
O2—C1—C2—O3	179.30 (7)	O4—C3—C4—O5	−178.95 (7)
O1—C1—C2—C3	123.19 (9)	C2—C3—C4—O5	−54.34 (9)
O2—C1—C2—C3	−59.15 (10)	C8—O7—C5—C6	62.14 (15)
O3—C2—C3—O4	62.09 (8)	C7—N1—C6—C5	53.29 (13)
C1—C2—C3—O4	−58.03 (8)	O7—C5—C6—N1	−56.83 (13)
O3—C2—C3—C4	−63.83 (8)	C6—N1—C7—C8	−53.28 (12)
C1—C2—C3—C4	176.05 (7)	C5—O7—C8—C7	−61.96 (16)
O4—C3—C4—O6	0.98 (11)	N1—C7—C8—O7	56.73 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3i	0.856 (17)	2.036 (17)	2.8430 (11)	156.6 (15)
N1—H1A···O1W	0.888 (18)	1.888 (18)	2.7583 (13)	166.1 (16)
O1W—H1W···O4ii	0.825 (19)	2.013 (19)	2.8173 (11)	164.6 (18)
O1W—H2W···O5iii	0.848 (19)	1.921 (19)	2.7542 (11)	167.2 (17)
O2—H2A···O6iv	0.958 (19)	1.584 (19)	2.5412 (10)	177.3 (17)
O3—H3A···O5v	0.911 (17)	1.742 (17)	2.6398 (9)	167.9 (15)
O4—H4A···O7	0.868 (16)	1.939 (16)	2.7818 (10)	163.4 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3i	0.856 (17)	2.036 (17)	2.8430 (11)	156.6 (15)
N1—H1A⋯O1W	0.888 (18)	1.888 (18)	2.7583 (13)	166.1 (16)
O1W—H1W⋯O4ii	0.825 (19)	2.013 (19)	2.8173 (11)	164.6 (18)
O1W—H2W⋯O5iii	0.848 (19)	1.921 (19)	2.7542 (11)	167.2 (17)
O2—H2A⋯O6iv	0.958 (19)	1.584 (19)	2.5412 (10)	177.3 (17)
O3—H3A⋯O5v	0.911 (17)	1.742 (17)	2.6398 (9)	167.9 (15)
O4—H4A⋯O7	0.868 (16)	1.939 (16)	2.7818 (10)	163.4 (14)

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