2-(4-Hydroxy­styr­yl)-1-methyl­pyridinium 4-methoxy­benzene­sulfonate

In the title compound, C₁₄H₁₄NO⁺·C₇H₇SO₄⁻, the cation is almost planar and adopts an E configuration. The pyridinium and benzene rings of the cation make dihedral angles of 88.01 (8) and 87.37 (8)°, respectively, with the benzene ring of the anion. In the crystal structure, the cations and anions are arranged in layers parallel to the (011) plane. The cations and anions are linked through O—H...O and C—H...O hydrogen bonds, and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.165
• Data-to-parameter ratio = 27.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-(4-Hydroxystyryl)-1-methylpyridinium 4-methoxybenzenesulfonate

Crystal data

C14H14NO^+·C7H7O4S^−	F(000) = 840
Mr = 399.46	Dx = 1.378 Mg m^−3
Monoclinic, P21/c	Melting point = 524–526 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.8786 (1) Å	Cell parameters from 4860 reflections
b = 17.2639 (2) Å	θ = 1.7–34.0°
c = 17.2828 (3) Å	µ = 0.20 mm^−1
β = 110.231 (1)°	T = 297 K
V = 1925.74 (5) Å^3	Block, yellow
Z = 4	0.54 × 0.40 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	7859 independent reflections
Radiation source: fine-focus sealed tube	4860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 8.33 pixels mm^-1	θmax = 34.0°, θmin = 1.7°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −27→27
Tmin = 0.899, Tmax = 0.940	l = −27→27
33183 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0738P)^2 + 0.3021P] where P = (Fo^2 + 2Fc^2)/3
7859 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

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	Occ. (<1)
S1	0.51037 (6)	0.58817 (2)	0.17076 (2)	0.04601 (11)
N1	0.06323 (19)	0.88458 (7)	0.34834 (7)	0.0424 (3)
O1	1.3636 (2)	0.72526 (9)	0.57664 (11)	0.0800 (5)
H1O1	1.393 (5)	0.7563 (18)	0.6092 (18)	0.109 (11)*
O2	1.2928 (2)	0.47282 (9)	0.41334 (9)	0.0750 (4)
O3A	0.3452 (11)	0.5336 (5)	0.1550 (6)	0.090 (2)	0.56
O4A	0.4754 (5)	0.66160 (19)	0.20215 (19)	0.0708 (8)	0.56
O5A	0.5627 (7)	0.6002 (2)	0.0948 (2)	0.0739 (10)	0.56
O3B	0.3910 (13)	0.5224 (7)	0.1395 (7)	0.083 (2)	0.44
O4B	0.4157 (7)	0.6343 (3)	0.2225 (3)	0.0762 (13)	0.44
O5B	0.5616 (7)	0.6350 (2)	0.1160 (3)	0.0603 (10)	0.44
C1	−0.1405 (2)	0.88992 (9)	0.30260 (10)	0.0491 (3)
H1B	−0.2216	0.9267	0.3165	0.059*
C2	−0.2297 (2)	0.84265 (10)	0.23666 (10)	0.0525 (4)
H2A	−0.3704	0.8465	0.2063	0.063*
C3	−0.1076 (3)	0.78891 (10)	0.21562 (10)	0.0537 (4)
H3A	−0.1648	0.7569	0.1701	0.064*
C4	0.0991 (2)	0.78311 (10)	0.26252 (10)	0.0521 (4)
H4A	0.1811	0.7468	0.2484	0.062*
C5	0.1882 (2)	0.83093 (8)	0.33109 (9)	0.0432 (3)
C6	0.4030 (2)	0.82477 (10)	0.38459 (10)	0.0505 (4)
H6A	0.4514	0.8603	0.4275	0.061*
C7	0.5348 (2)	0.77225 (9)	0.37671 (9)	0.0463 (3)
H7A	0.4853	0.7382	0.3325	0.056*
C8	0.7495 (2)	0.76211 (9)	0.43012 (8)	0.0426 (3)
C9	0.8708 (3)	0.70567 (10)	0.41119 (10)	0.0518 (4)
H9A	0.8131	0.6753	0.3644	0.062*
C10	1.0742 (3)	0.69383 (10)	0.46026 (11)	0.0575 (4)
H10A	1.1521	0.6557	0.4466	0.069*
C11	1.1628 (2)	0.73890 (9)	0.53009 (11)	0.0521 (4)
C12	1.0448 (2)	0.79556 (9)	0.54980 (9)	0.0493 (3)
H12A	1.1034	0.8259	0.5966	0.059*
C13	0.8417 (2)	0.80724 (9)	0.50072 (9)	0.0465 (3)
H13A	0.7646	0.8456	0.5146	0.056*
C14	0.1463 (3)	0.93931 (10)	0.41805 (10)	0.0542 (4)
H14A	0.0371	0.9726	0.4208	0.081*
H14B	0.2540	0.9700	0.4099	0.081*
H14C	0.2018	0.9108	0.4686	0.081*
C15	0.7401 (2)	0.55075 (8)	0.24370 (8)	0.0413 (3)
C16	0.7325 (3)	0.49846 (9)	0.30314 (10)	0.0526 (4)
H16A	0.6050	0.4815	0.3041	0.063*
C17	0.9152 (3)	0.47079 (10)	0.36189 (11)	0.0577 (4)
H17A	0.9099	0.4354	0.4017	0.069*
C18	1.1040 (3)	0.49669 (10)	0.36012 (10)	0.0528 (4)
C19	1.1121 (3)	0.54955 (10)	0.30105 (11)	0.0526 (4)
H19A	1.2395	0.5672	0.3006	0.063*
C20	0.9321 (2)	0.57589 (9)	0.24323 (10)	0.0466 (3)
H20A	0.9384	0.6109	0.2033	0.056*
C21	1.2976 (4)	0.41762 (14)	0.47507 (14)	0.0844 (7)
H21D	1.4388	0.4043	0.5058	0.127*
H21A	1.2233	0.3720	0.4494	0.127*
H21B	1.2340	0.4394	0.5116	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.04326 (19)	0.0452 (2)	0.0479 (2)	−0.00399 (14)	0.01362 (15)	0.00237 (14)
N1	0.0461 (6)	0.0385 (5)	0.0411 (6)	−0.0027 (5)	0.0131 (5)	0.0018 (4)
O1	0.0485 (7)	0.0608 (8)	0.1027 (12)	0.0126 (6)	−0.0095 (7)	−0.0126 (8)
O2	0.0589 (8)	0.0795 (9)	0.0746 (9)	0.0066 (7)	0.0076 (7)	0.0166 (7)
O3A	0.046 (2)	0.084 (4)	0.124 (5)	−0.023 (2)	0.007 (2)	0.042 (3)
O4A	0.070 (2)	0.0662 (18)	0.0581 (17)	0.0257 (14)	−0.0009 (13)	−0.0133 (13)
O5A	0.0731 (18)	0.105 (3)	0.0477 (16)	0.019 (2)	0.0259 (14)	0.0198 (17)
O3B	0.052 (4)	0.070 (3)	0.100 (4)	−0.020 (3)	−0.007 (3)	−0.001 (3)
O4B	0.071 (3)	0.097 (3)	0.067 (2)	0.033 (2)	0.0312 (18)	0.012 (2)
O5B	0.0558 (18)	0.068 (2)	0.063 (2)	−0.0013 (19)	0.0275 (17)	0.0227 (18)
C1	0.0458 (8)	0.0449 (7)	0.0550 (8)	0.0054 (6)	0.0152 (7)	0.0067 (6)
C2	0.0411 (7)	0.0533 (8)	0.0550 (8)	−0.0007 (6)	0.0063 (6)	0.0048 (7)
C3	0.0497 (8)	0.0520 (8)	0.0503 (8)	−0.0060 (7)	0.0055 (7)	−0.0055 (7)
C4	0.0459 (8)	0.0536 (8)	0.0509 (8)	−0.0009 (7)	0.0093 (6)	−0.0117 (7)
C5	0.0410 (7)	0.0430 (7)	0.0435 (7)	−0.0032 (6)	0.0118 (6)	−0.0017 (5)
C6	0.0418 (7)	0.0544 (8)	0.0494 (8)	−0.0042 (6)	0.0080 (6)	−0.0111 (6)
C7	0.0432 (7)	0.0514 (8)	0.0404 (7)	−0.0051 (6)	0.0095 (6)	−0.0030 (6)
C8	0.0420 (7)	0.0481 (7)	0.0375 (6)	−0.0041 (6)	0.0135 (5)	−0.0008 (5)
C9	0.0509 (8)	0.0520 (8)	0.0494 (8)	−0.0021 (7)	0.0136 (7)	−0.0096 (6)
C10	0.0511 (9)	0.0482 (8)	0.0702 (11)	0.0042 (7)	0.0173 (8)	−0.0085 (7)
C11	0.0419 (7)	0.0457 (8)	0.0608 (9)	0.0012 (6)	0.0075 (7)	0.0030 (7)
C12	0.0437 (7)	0.0540 (8)	0.0445 (7)	−0.0027 (6)	0.0079 (6)	−0.0056 (6)
C13	0.0421 (7)	0.0537 (8)	0.0434 (7)	0.0002 (6)	0.0146 (6)	−0.0066 (6)
C14	0.0646 (10)	0.0469 (8)	0.0482 (8)	−0.0019 (7)	0.0159 (7)	−0.0061 (6)
C15	0.0462 (7)	0.0373 (6)	0.0422 (6)	−0.0008 (5)	0.0176 (6)	−0.0017 (5)
C16	0.0534 (9)	0.0504 (8)	0.0565 (9)	−0.0035 (7)	0.0224 (7)	0.0084 (7)
C17	0.0687 (11)	0.0511 (9)	0.0541 (9)	−0.0004 (8)	0.0225 (8)	0.0126 (7)
C18	0.0537 (9)	0.0479 (8)	0.0537 (8)	0.0043 (7)	0.0145 (7)	−0.0024 (7)
C19	0.0481 (8)	0.0508 (8)	0.0627 (9)	−0.0011 (7)	0.0238 (7)	−0.0010 (7)
C20	0.0497 (8)	0.0430 (7)	0.0518 (8)	−0.0011 (6)	0.0236 (7)	0.0014 (6)
C21	0.0864 (16)	0.0857 (15)	0.0650 (12)	0.0158 (12)	0.0057 (11)	0.0192 (11)

Geometric parameters (Å, º)

S1—O5B	1.379 (4)	C8—C9	1.393 (2)
S1—O3B	1.396 (10)	C8—C13	1.401 (2)
S1—O3A	1.427 (7)	C9—C10	1.378 (2)
S1—O4A	1.432 (3)	C9—H9A	0.93
S1—O5A	1.491 (3)	C10—C11	1.387 (2)
S1—O4B	1.504 (4)	C10—H10A	0.93
S1—C15	1.7683 (15)	C11—C12	1.387 (2)
N1—C1	1.3531 (19)	C12—C13	1.375 (2)
N1—C5	1.3648 (19)	C12—H12A	0.93
N1—C14	1.4816 (19)	C13—H13A	0.93
O1—C11	1.357 (2)	C14—H14A	0.96
O1—H1O1	0.75 (3)	C14—H14B	0.96
O2—C18	1.370 (2)	C14—H14C	0.96
O2—C21	1.422 (3)	C15—C16	1.382 (2)
C1—C2	1.363 (2)	C15—C20	1.393 (2)
C1—H1B	0.93	C16—C17	1.398 (2)
C2—C3	1.381 (2)	C16—H16A	0.93
C2—H2A	0.93	C17—C18	1.383 (3)
C3—C4	1.376 (2)	C17—H17A	0.93
C3—H3A	0.93	C18—C19	1.385 (2)
C4—C5	1.400 (2)	C19—C20	1.372 (2)
C4—H4A	0.93	C19—H19A	0.93
C5—C6	1.451 (2)	C20—H20A	0.93
C6—C7	1.322 (2)	C21—H21D	0.96
C6—H6A	0.93	C21—H21A	0.96
C7—C8	1.4562 (19)	C21—H21B	0.96
C7—H7A	0.93
O5B—S1—O3B	117.9 (5)	C13—C8—C7	122.67 (14)
O5B—S1—O3A	129.1 (4)	C10—C9—C8	121.49 (14)
O5B—S1—O4A	81.8 (2)	C10—C9—H9A	119.3
O3B—S1—O4A	135.5 (4)	C8—C9—H9A	119.3
O3A—S1—O4A	115.5 (4)	C9—C10—C11	119.96 (15)
O3B—S1—O5A	93.6 (5)	C9—C10—H10A	120.0
O3A—S1—O5A	110.0 (4)	C11—C10—H10A	120.0
O4A—S1—O5A	109.5 (2)	O1—C11—C12	122.61 (15)
O5B—S1—O4B	111.3 (2)	O1—C11—C10	117.99 (16)
O3B—S1—O4B	110.1 (5)	C12—C11—C10	119.39 (15)
O3A—S1—O4B	89.0 (4)	C13—C12—C11	120.53 (14)
O5A—S1—O4B	137.4 (2)	C13—C12—H12A	119.7
O5B—S1—C15	109.0 (2)	C11—C12—H12A	119.7
O3B—S1—C15	103.8 (5)	C12—C13—C8	120.86 (14)
O3A—S1—C15	110.6 (4)	C12—C13—H13A	119.6
O4A—S1—C15	106.21 (13)	C8—C13—H13A	119.6
O5A—S1—C15	104.50 (16)	N1—C14—H14A	109.5
O4B—S1—C15	103.52 (18)	N1—C14—H14B	109.5
C1—N1—C5	121.47 (13)	H14A—C14—H14B	109.5
C1—N1—C14	117.52 (13)	N1—C14—H14C	109.5
C5—N1—C14	121.02 (13)	H14A—C14—H14C	109.5
C11—O1—H1O1	106 (2)	H14B—C14—H14C	109.5
C18—O2—C21	118.40 (17)	C16—C15—C20	119.18 (14)
N1—C1—C2	121.56 (15)	C16—C15—S1	120.95 (12)
N1—C1—H1B	119.2	C20—C15—S1	119.83 (11)
C2—C1—H1B	119.2	C15—C16—C17	120.49 (15)
C1—C2—C3	118.91 (15)	C15—C16—H16A	119.8
C1—C2—H2A	120.5	C17—C16—H16A	119.8
C3—C2—H2A	120.5	C18—C17—C16	119.22 (15)
C4—C3—C2	119.49 (15)	C18—C17—H17A	120.4
C4—C3—H3A	120.3	C16—C17—H17A	120.4
C2—C3—H3A	120.3	O2—C18—C17	124.56 (16)
C3—C4—C5	121.12 (15)	O2—C18—C19	114.98 (16)
C3—C4—H4A	119.4	C17—C18—C19	120.46 (16)
C5—C4—H4A	119.4	C20—C19—C18	119.92 (15)
N1—C5—C4	117.43 (13)	C20—C19—H19A	120.0
N1—C5—C6	119.35 (13)	C18—C19—H19A	120.0
C4—C5—C6	123.21 (14)	C19—C20—C15	120.73 (14)
C7—C6—C5	124.62 (14)	C19—C20—H20A	119.6
C7—C6—H6A	117.7	C15—C20—H20A	119.6
C5—C6—H6A	117.7	O2—C21—H21D	109.5
C6—C7—C8	126.75 (14)	O2—C21—H21A	109.5
C6—C7—H7A	116.6	H21D—C21—H21A	109.5
C8—C7—H7A	116.6	O2—C21—H21B	109.5
C9—C8—C13	117.77 (14)	H21D—C21—H21B	109.5
C9—C8—C7	119.56 (13)	H21A—C21—H21B	109.5
C5—N1—C1—C2	−0.8 (2)	C7—C8—C13—C12	179.67 (14)
C14—N1—C1—C2	179.12 (15)	O5B—S1—C15—C16	−176.4 (2)
N1—C1—C2—C3	−1.0 (2)	O3B—S1—C15—C16	−50.0 (5)
C1—C2—C3—C4	1.4 (2)	O3A—S1—C15—C16	−29.1 (4)
C2—C3—C4—C5	−0.2 (3)	O4A—S1—C15—C16	96.9 (2)
C1—N1—C5—C4	2.0 (2)	O5A—S1—C15—C16	−147.4 (2)
C14—N1—C5—C4	−177.92 (14)	O4B—S1—C15—C16	65.1 (2)
C1—N1—C5—C6	−176.73 (14)	O5B—S1—C15—C20	5.6 (2)
C14—N1—C5—C6	3.4 (2)	O3B—S1—C15—C20	132.1 (5)
C3—C4—C5—N1	−1.5 (2)	O3A—S1—C15—C20	153.0 (4)
C3—C4—C5—C6	177.17 (16)	O4A—S1—C15—C20	−81.1 (2)
N1—C5—C6—C7	175.96 (15)	O5A—S1—C15—C20	34.6 (2)
C4—C5—C6—C7	−2.7 (3)	O4B—S1—C15—C20	−112.9 (2)
C5—C6—C7—C8	−177.96 (14)	C20—C15—C16—C17	−0.3 (2)
C6—C7—C8—C9	−177.33 (16)	S1—C15—C16—C17	−178.30 (13)
C6—C7—C8—C13	2.5 (3)	C15—C16—C17—C18	0.3 (3)
C13—C8—C9—C10	0.5 (2)	C21—O2—C18—C17	0.0 (3)
C7—C8—C9—C10	−179.65 (15)	C21—O2—C18—C19	−179.07 (17)
C8—C9—C10—C11	−0.3 (3)	C16—C17—C18—O2	−178.80 (16)
C9—C10—C11—O1	179.99 (17)	C16—C17—C18—C19	0.2 (3)
C9—C10—C11—C12	0.1 (3)	O2—C18—C19—C20	178.35 (15)
O1—C11—C12—C13	−179.97 (17)	C17—C18—C19—C20	−0.7 (3)
C10—C11—C12—C13	0.0 (3)	C18—C19—C20—C15	0.8 (2)
C11—C12—C13—C8	0.3 (2)	C16—C15—C20—C19	−0.2 (2)
C9—C8—C13—C12	−0.5 (2)	S1—C15—C20—C19	177.78 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O4A^i	0.75 (3)	2.07 (3)	2.821 (4)	178 (4)
C1—H1B···O3A^ii	0.93	2.16	3.064 (9)	164
C7—H7A···O4A	0.93	2.59	3.473 (3)	158
C12—H12A···O4A^i	0.93	2.59	3.295 (4)	133
C13—H13A···O5A^iii	0.93	2.46	3.322 (5)	154
C14—H14B···O5A^iv	0.96	2.59	3.475 (4)	153
C21—H21A···Cg1^v	0.96	2.92	3.610 (3)	130

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x+2, −y+1, −z+1.