Ethyl [(2-hydroxy-phen-yl)(pyridinium-2-ylamino)meth-yl]phospho-nate methanol solvate.

In the title compound, C(14)H(17)N(2)O(4)P·CH(3)OH, the planes of the pyridinium-2-ylamino and 2-hydroxy-phenyl groups form a dihedral angle of 75.6 (1)°, with the pyridinium NH group and the 2-hydroxy-phenyl OH group pointing in opposite directions. Three intra-molecular hydrogen bonds are observed. Two phospho-nate and two methanol mol-ecules are connected by O-H⋯O hydrogen bonds as a centrosymmetric dimeric cluster, and inter-act further with other dimeric clusters via N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions, resulting in a sheet structure.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Briceño et al. (2007 ▶); Foster & Weinhold (1980 ▶); Jeffrey et al. (1985 ▶); Kaboudin & Moradi (2005 ▶); Kachkovskyi & Kolodiazhnyi (2007 ▶); Kafarski & Lejczak (2001 ▶); Liu et al. (2002 ▶); Meyer et al. (2004 ▶); Palacios et al. (2005 ▶); Rohovec et al. (1999 ▶).

Experimental

Crystal data

pan class="Chemical">C14H17N2O4P·CH4O

M = 340.31

Monoclinic,

a = 12.821 (3) Å

b = 9.536 (2) Å

c = 16.567 (3) Å

β = 122.308 (14)°

V = 1711.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 298 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.875, T max = 0.964

6784 measured reflections

2991 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.147

S = 1.14

2991 reflections

210 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015675/cf2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015675/cf2201Isup2.hkl

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

C14H17N2O4P·CH4O	F000 = 720
Mr = 340.31	Dx = 1.320 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1906 reflections
a = 12.821 (3) Å	θ = 2.5–23.8º
b = 9.536 (2) Å	µ = 0.19 mm−1
c = 16.567 (3) Å	T = 298 (2) K
β = 122.308 (14)º	Block, colourless
V = 1711.9 (6) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1K CCD diffractometer	2991 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −15→15
Tmin = 0.875, Tmax = 0.964	k = −11→8
6784 measured reflections	l = −17→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.052P)2 + 1.1778P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
2991 reflections	Δρmax = 0.34 e Å−3
210 parameters	Δρmin = −0.34 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
P1	0.75798 (7)	0.45914 (9)	0.40161 (6)	0.0359 (3)
O1	0.5572 (2)	0.7872 (3)	0.22842 (16)	0.0561 (7)
H1	0.5007	0.8424	0.1964	0.067*
O2	0.7741 (2)	0.3583 (3)	0.33273 (18)	0.0578 (7)
O3	0.86639 (19)	0.4487 (2)	0.50109 (15)	0.0466 (6)
O4	0.63500 (19)	0.4400 (2)	0.38884 (15)	0.0481 (6)
N1	0.8906 (2)	0.6464 (3)	0.37455 (17)	0.0390 (7)
H1A	0.9521	0.6023	0.4221	0.047*
N2	1.0392 (2)	0.7331 (3)	0.35182 (17)	0.0381 (6)
H2A	1.0852	0.6775	0.3996	0.046*
C1	0.6172 (3)	0.8248 (3)	0.3218 (2)	0.0417 (8)
C2	0.5805 (3)	0.9373 (4)	0.3538 (3)	0.0552 (10)
H2	0.5115	0.9893	0.3105	0.066*
C3	0.6448 (4)	0.9723 (4)	0.4481 (3)	0.0681 (12)
H3	0.6190	1.0475	0.4690	0.082*
C4	0.7468 (4)	0.8976 (5)	0.5121 (3)	0.0713 (12)
H4	0.7905	0.9215	0.5765	0.086*
C5	0.7848 (3)	0.7865 (4)	0.4808 (2)	0.0545 (10)
H5	0.8549	0.7364	0.5246	0.065*
C6	0.7210 (3)	0.7479 (3)	0.3857 (2)	0.0373 (7)
C7	0.7639 (3)	0.6274 (3)	0.3523 (2)	0.0352 (7)
H7	0.7091	0.6217	0.2827	0.042*
C8	0.9195 (3)	0.7286 (3)	0.3241 (2)	0.0336 (7)
C9	0.8361 (3)	0.8096 (3)	0.2451 (2)	0.0415 (8)
H9	0.7530	0.8119	0.2249	0.050*
C10	0.8774 (3)	0.8845 (4)	0.1985 (2)	0.0531 (10)
H10	0.8219	0.9379	0.1457	0.064*
C11	1.0008 (4)	0.8832 (4)	0.2277 (3)	0.0559 (10)
H11	1.0282	0.9341	0.1946	0.067*
C12	1.0803 (3)	0.8069 (4)	0.3050 (3)	0.0479 (9)
H12	1.1637	0.8051	0.3260	0.057*
C13	0.7568 (5)	0.2100 (5)	0.3340 (4)	0.0900 (15)
H13A	0.7122	0.1760	0.2687	0.108*
H13B	0.7055	0.1931	0.3598	0.108*
C14	0.8694 (6)	0.1287 (6)	0.3889 (5)	0.126 (2)
H14A	0.9171	0.1363	0.3600	0.189*
H14B	0.8489	0.0322	0.3899	0.189*
H14C	0.9165	0.1640	0.4530	0.189*
O5	0.6628 (3)	0.3431 (4)	0.5586 (2)	0.0890 (10)
H5A	0.6514	0.3728	0.5080	0.107*
C15	0.5492 (6)	0.3157 (8)	0.5475 (5)	0.125 (2)
H15A	0.4896	0.2940	0.4818	0.187*
H15B	0.5226	0.3967	0.5661	0.187*
H15C	0.5571	0.2375	0.5868	0.187*

	U11	U22	U33	U12	U13	U23
P1	0.0292 (4)	0.0369 (5)	0.0371 (5)	−0.0019 (4)	0.0146 (4)	0.0050 (4)
O1	0.0374 (13)	0.0611 (17)	0.0480 (15)	0.0195 (12)	0.0082 (11)	0.0025 (12)
O2	0.0709 (17)	0.0395 (14)	0.0736 (17)	−0.0025 (12)	0.0458 (15)	−0.0012 (12)
O3	0.0325 (12)	0.0521 (15)	0.0422 (13)	0.0002 (10)	0.0113 (10)	0.0174 (11)
O4	0.0320 (12)	0.0570 (15)	0.0480 (13)	−0.0098 (11)	0.0164 (11)	−0.0010 (11)
N1	0.0282 (13)	0.0438 (16)	0.0367 (14)	0.0043 (12)	0.0117 (12)	0.0146 (12)
N2	0.0345 (14)	0.0380 (15)	0.0376 (15)	0.0027 (12)	0.0165 (12)	0.0066 (12)
C1	0.0335 (17)	0.0407 (19)	0.048 (2)	−0.0008 (15)	0.0203 (16)	0.0013 (16)
C2	0.052 (2)	0.044 (2)	0.071 (3)	0.0119 (17)	0.034 (2)	0.0047 (19)
C3	0.087 (3)	0.051 (3)	0.077 (3)	0.009 (2)	0.050 (3)	−0.012 (2)
C4	0.094 (3)	0.060 (3)	0.053 (2)	−0.001 (2)	0.035 (2)	−0.013 (2)
C5	0.059 (2)	0.049 (2)	0.044 (2)	0.0051 (18)	0.0207 (18)	0.0018 (17)
C6	0.0353 (17)	0.0355 (18)	0.0393 (18)	−0.0013 (14)	0.0188 (15)	0.0040 (14)
C7	0.0259 (15)	0.0401 (18)	0.0308 (16)	0.0009 (13)	0.0093 (13)	0.0038 (13)
C8	0.0355 (17)	0.0302 (16)	0.0327 (16)	0.0000 (13)	0.0165 (14)	0.0021 (13)
C9	0.0400 (18)	0.045 (2)	0.0394 (18)	0.0051 (15)	0.0210 (15)	0.0112 (15)
C10	0.061 (2)	0.052 (2)	0.043 (2)	0.0107 (19)	0.0250 (18)	0.0176 (17)
C11	0.066 (3)	0.052 (2)	0.065 (2)	0.001 (2)	0.045 (2)	0.0142 (19)
C12	0.047 (2)	0.047 (2)	0.059 (2)	−0.0012 (17)	0.0350 (19)	0.0043 (18)
C13	0.100 (4)	0.048 (3)	0.121 (4)	−0.006 (3)	0.059 (3)	−0.009 (3)
C14	0.135 (5)	0.074 (4)	0.176 (6)	0.008 (4)	0.088 (5)	0.001 (4)
O5	0.073 (2)	0.127 (3)	0.0708 (19)	0.0061 (19)	0.0411 (17)	0.0241 (19)
C15	0.113 (5)	0.144 (6)	0.158 (6)	−0.003 (4)	0.099 (5)	0.024 (5)

P1—O4	1.486 (2)	C5—H5	0.930
P1—O3	1.486 (2)	C6—C7	1.502 (4)
P1—O2	1.588 (3)	C7—H7	0.980
P1—C7	1.821 (3)	C8—C9	1.399 (4)
O1—C1	1.357 (4)	C9—C10	1.351 (4)
O1—H1	0.820	C9—H9	0.930
O2—C13	1.433 (5)	C10—C11	1.386 (5)
N1—C8	1.334 (4)	C10—H10	0.930
N1—C7	1.473 (4)	C11—C12	1.347 (5)
N1—H1A	0.869	C11—H11	0.930
N2—C8	1.347 (4)	C12—H12	0.930
N2—C12	1.347 (4)	C13—C14	1.451 (6)
N2—H2A	0.870	C13—H13A	0.970
C1—C2	1.385 (5)	C13—H13B	0.970
C1—C6	1.387 (4)	C14—H14A	0.960
C2—C3	1.363 (5)	C14—H14B	0.960
C2—H2	0.930	C14—H14C	0.960
C3—C4	1.364 (6)	O5—C15	1.391 (6)
C3—H3	0.930	O5—H5A	0.821
C4—C5	1.378 (5)	C15—H15A	0.960
C4—H4	0.930	C15—H15B	0.960
C5—C6	1.381 (4)	C15—H15C	0.960
O4—P1—O3	116.22 (13)	C6—C7—H7	107.7
O4—P1—O2	111.04 (14)	P1—C7—H7	107.7
O3—P1—O2	110.63 (14)	N1—C8—N2	116.9 (3)
O4—P1—C7	109.88 (14)	N1—C8—C9	125.5 (3)
O3—P1—C7	108.56 (13)	N2—C8—C9	117.6 (3)
O2—P1—C7	99.12 (14)	C10—C9—C8	119.3 (3)
C1—O1—H1	109.5	C10—C9—H9	120.4
C13—O2—P1	120.4 (3)	C8—C9—H9	120.4
C8—N1—C7	123.6 (2)	C9—C10—C11	121.3 (3)
C8—N1—H1A	115.6	C9—C10—H10	119.3
C7—N1—H1A	120.8	C11—C10—H10	119.3
C8—N2—C12	123.1 (3)	C12—C11—C10	118.6 (3)
C8—N2—H2A	112.8	C12—C11—H11	120.7
C12—N2—H2A	123.9	C10—C11—H11	120.7
O1—C1—C2	122.6 (3)	N2—C12—C11	120.0 (3)
O1—C1—C6	117.3 (3)	N2—C12—H12	120.0
C2—C1—C6	120.1 (3)	C11—C12—H12	120.0
C3—C2—C1	120.5 (4)	O2—C13—C14	115.2 (4)
C3—C2—H2	119.7	O2—C13—H13A	108.5
C1—C2—H2	119.7	C14—C13—H13A	108.5
C2—C3—C4	120.2 (4)	O2—C13—H13B	108.5
C2—C3—H3	119.9	C14—C13—H13B	108.5
C4—C3—H3	119.9	H13A—C13—H13B	107.5
C3—C4—C5	119.7 (4)	C13—C14—H14A	109.5
C3—C4—H4	120.2	C13—C14—H14B	109.5
C5—C4—H4	120.2	H14A—C14—H14B	109.5
C4—C5—C6	121.4 (4)	C13—C14—H14C	109.5
C4—C5—H5	119.3	H14A—C14—H14C	109.5
C6—C5—H5	119.3	H14B—C14—H14C	109.5
C5—C6—C1	118.1 (3)	C15—O5—H5A	109.1
C5—C6—C7	120.9 (3)	O5—C15—H15A	109.5
C1—C6—C7	120.9 (3)	O5—C15—H15B	109.5
N1—C7—C6	112.7 (3)	H15A—C15—H15B	109.5
N1—C7—P1	107.5 (2)	O5—C15—H15C	109.5
C6—C7—P1	113.4 (2)	H15A—C15—H15C	109.5
N1—C7—H7	107.7	H15B—C15—H15C	109.5
O4—P1—O2—C13	−55.0 (3)	C1—C6—C7—P1	−116.5 (3)
O3—P1—O2—C13	75.6 (3)	O4—P1—C7—N1	174.96 (19)
C7—P1—O2—C13	−170.5 (3)	O3—P1—C7—N1	46.9 (2)
O1—C1—C2—C3	−179.0 (3)	O2—P1—C7—N1	−68.6 (2)
C6—C1—C2—C3	−0.9 (5)	O4—P1—C7—C6	49.7 (2)
C1—C2—C3—C4	0.6 (6)	O3—P1—C7—C6	−78.4 (2)
C2—C3—C4—C5	0.1 (7)	O2—P1—C7—C6	166.1 (2)
C3—C4—C5—C6	−0.6 (6)	C7—N1—C8—N2	−178.6 (3)
C4—C5—C6—C1	0.3 (5)	C7—N1—C8—C9	1.3 (5)
C4—C5—C6—C7	179.4 (3)	C12—N2—C8—N1	177.1 (3)
O1—C1—C6—C5	178.6 (3)	C12—N2—C8—C9	−2.7 (5)
C2—C1—C6—C5	0.4 (5)	N1—C8—C9—C10	−177.7 (3)
O1—C1—C6—C7	−0.5 (4)	N2—C8—C9—C10	2.1 (5)
C2—C1—C6—C7	−178.7 (3)	C8—C9—C10—C11	−0.4 (5)
C8—N1—C7—C6	−78.5 (4)	C9—C10—C11—C12	−0.9 (6)
C8—N1—C7—P1	155.8 (2)	C8—N2—C12—C11	1.5 (5)
C5—C6—C7—N1	−58.0 (4)	C10—C11—C12—N2	0.4 (6)
C1—C6—C7—N1	121.0 (3)	P1—O2—C13—C14	−99.2 (5)
C5—C6—C7—P1	64.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.87	2.57	2.957 (3)	108
N2—H2A···O3i	0.87	1.86	2.692 (3)	160
N1—H1A···O3i	0.87	2.03	2.813 (3)	150
O1—H1···O4ii	0.82	1.81	2.618 (3)	170
C7—H7···O1	0.98	2.28	2.783 (4)	111
C9—H9···O1	0.93	2.55	3.438 (5)	160
C12—H12···O5i	0.93	2.46	3.169 (5)	133
O5—H5A···O4	0.82	1.98	2.795 (4)	176
C14—H14B···Cgiii	0.96	2.91	3.697 (8)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.87	2.57	2.957 (3)	108
N2—H2A⋯O3i	0.87	1.86	2.692 (3)	160
N1—H1A⋯O3i	0.87	2.03	2.813 (3)	150
O1—H1⋯O4ii	0.82	1.81	2.618 (3)	170
C7—H7⋯O1	0.98	2.28	2.783 (4)	111
C9—H9⋯O1	0.93	2.55	3.438 (5)	160
C12—H12⋯O5i	0.93	2.46	3.169 (5)	133
O5—H5A⋯O4	0.82	1.98	2.795 (4)	176
C14—H14B⋯Cgiii	0.96	2.91	3.697 (8)	141

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