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In the title compound, C19H18NO+·C7H7O4S·H2O, the cation adopts an E configuration and is almost planar. The quinolinium group and benzene ring of the cation make dihedral angles of 84.40 (8) and 85.80 (11)°, respectively, with the benzene ring of the anion. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds together with weak intra- and inter­molecular C—H...O inter­actions. The cations are arranged in one-dimensional chains along the b axis and these chains are inter­connected with the anions through weak C—H...O inter­actions. The water mol­ecules are also hydrogen-bonded to the anions to form a three-dimensional network. C—H...π inter­actions are also observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048124/sj2167sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048124/sj2167Isup2.hkl
Contains datablock I

CCDC reference: 630480

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.154
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10A .. H18A .. 1.89 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 1 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 0 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

Computing details top

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-[(E)-2-(4-methoxyphenyl)ethenyl]-1-methylquinolinium 4-methoxybenzenesulfonate monohydrate top
Crystal data top
C19H18NO+·C7H7SO4·H2OF(000) = 1016
Mr = 481.55Dx = 1.401 Mg m3
Monoclinic, P21/cMelting point = 500–502 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.6155 (2) ÅCell parameters from 4300 reflections
b = 8.3133 (1) Åθ = 1.4–28.0°
c = 19.3131 (2) ŵ = 0.19 mm1
β = 103.401 (1)°T = 100 K
V = 2282.71 (5) Å3Plate, yellow
Z = 40.27 × 0.25 × 0.08 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5509 independent reflections
Radiation source: fine-focus sealed tube4300 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 1.4°
ω scansh = 1919
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.951, Tmax = 0.986l = 2525
41723 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0766P)2 + 2.0189P]
where P = (Fo2 + 2Fc2)/3
5509 reflections(Δ/σ)max < 0.001
318 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Å2) top
xyzUiso*/Ueq
S10.17217 (4)0.34520 (6)0.30030 (3)0.02255 (15)
O10.44076 (12)1.1927 (2)0.07816 (8)0.0343 (4)
O20.22765 (13)0.2064 (2)0.33114 (11)0.0433 (5)
O30.13000 (12)0.3269 (2)0.22498 (8)0.0329 (4)
O40.10325 (11)0.3946 (2)0.33977 (8)0.0316 (4)
O50.45095 (11)0.86949 (19)0.31982 (9)0.0298 (4)
N10.09691 (12)0.6576 (2)0.05671 (8)0.0191 (3)
C10.17821 (14)0.5683 (3)0.05822 (10)0.0203 (4)
C20.24179 (15)0.5315 (3)0.12284 (11)0.0258 (5)
H2A0.23100.56890.16560.031*
C30.31954 (17)0.4404 (3)0.12248 (12)0.0319 (5)
H3A0.36170.41720.16530.038*
C40.33680 (18)0.3812 (3)0.05881 (13)0.0348 (6)
H4A0.38950.31770.05990.042*
C50.27665 (17)0.4164 (3)0.00493 (12)0.0303 (5)
H5A0.28850.37680.04700.036*
C60.19610 (15)0.5134 (3)0.00670 (11)0.0232 (4)
C70.13263 (16)0.5567 (3)0.07138 (11)0.0247 (5)
H7A0.14210.51900.11450.030*
C80.05830 (15)0.6527 (3)0.07024 (11)0.0237 (4)
H8A0.01880.68430.11310.028*
C90.03904 (14)0.7064 (3)0.00540 (10)0.0206 (4)
C100.04164 (16)0.8062 (3)0.00526 (12)0.0285 (5)
H10A0.04840.84620.03820.034*
C110.10792 (16)0.8455 (3)0.06385 (12)0.0282 (5)
H11A0.10080.80600.10740.034*
C120.19009 (16)0.9456 (3)0.06392 (11)0.0270 (5)
C130.25055 (16)0.9838 (3)0.12905 (11)0.0283 (5)
H13A0.23520.95180.17110.034*
C140.33213 (16)1.0675 (3)0.13202 (11)0.0250 (5)
H14A0.37141.09270.17590.030*
C150.35638 (15)1.1151 (3)0.06930 (11)0.0229 (4)
C160.29610 (16)1.0826 (3)0.00349 (11)0.0237 (4)
H16A0.31131.11610.03840.028*
C170.21333 (16)1.0000 (3)0.00134 (11)0.0273 (5)
H17A0.17230.98010.04240.033*
C180.07539 (16)0.6935 (3)0.12659 (11)0.0259 (5)
H18A0.01080.72570.11940.039*
H18B0.11540.77880.14950.039*
H18C0.08610.59900.15600.039*
C190.4692 (2)1.2409 (4)0.01567 (13)0.0452 (7)
H19A0.53031.28970.02870.068*
H19B0.42481.31700.01030.068*
H19C0.47171.14840.01360.068*
C200.25369 (14)0.5059 (3)0.30847 (10)0.0201 (4)
C210.34928 (15)0.4730 (3)0.31667 (11)0.0235 (4)
H21A0.37020.36700.31960.028*
C220.41293 (15)0.5974 (3)0.32040 (11)0.0252 (5)
H22A0.47650.57490.32560.030*
C230.38202 (15)0.7568 (3)0.31643 (10)0.0225 (4)
C240.28698 (14)0.7911 (3)0.30920 (10)0.0212 (4)
H24A0.26620.89710.30690.025*
C250.22363 (14)0.6648 (3)0.30543 (10)0.0207 (4)
H25A0.16010.68710.30080.025*
C260.42440 (17)1.0346 (3)0.32281 (13)0.0317 (5)
H26A0.47911.10160.32830.048*
H26B0.39631.05040.36260.048*
H26C0.38001.06270.27960.048*
O1W0.07734 (14)0.9657 (3)0.24946 (11)0.0410 (5)
H2W10.016 (3)0.954 (4)0.2284 (19)0.064 (11)*
H1W10.092 (3)1.067 (5)0.242 (2)0.079 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0250 (3)0.0256 (3)0.0178 (2)0.0034 (2)0.00664 (19)0.00283 (19)
O10.0304 (9)0.0528 (11)0.0206 (8)0.0144 (8)0.0076 (6)0.0061 (7)
O20.0358 (10)0.0308 (10)0.0638 (13)0.0008 (8)0.0122 (9)0.0186 (9)
O30.0413 (10)0.0404 (10)0.0177 (7)0.0172 (8)0.0082 (7)0.0058 (7)
O40.0266 (8)0.0498 (11)0.0203 (7)0.0103 (7)0.0092 (6)0.0061 (7)
O50.0233 (8)0.0270 (8)0.0388 (9)0.0044 (6)0.0063 (7)0.0055 (7)
N10.0202 (8)0.0230 (9)0.0147 (7)0.0032 (7)0.0051 (6)0.0013 (6)
C10.0195 (10)0.0243 (11)0.0184 (9)0.0013 (8)0.0068 (8)0.0008 (8)
C20.0250 (11)0.0361 (13)0.0169 (9)0.0009 (9)0.0062 (8)0.0017 (8)
C30.0285 (12)0.0446 (14)0.0229 (11)0.0056 (10)0.0063 (9)0.0079 (10)
C40.0331 (13)0.0447 (15)0.0297 (12)0.0126 (11)0.0139 (10)0.0058 (10)
C50.0327 (12)0.0370 (13)0.0251 (11)0.0075 (10)0.0149 (9)0.0012 (9)
C60.0265 (10)0.0257 (11)0.0190 (9)0.0013 (9)0.0083 (8)0.0004 (8)
C70.0321 (11)0.0271 (11)0.0158 (9)0.0054 (9)0.0075 (8)0.0027 (8)
C80.0249 (10)0.0279 (11)0.0167 (9)0.0047 (9)0.0018 (8)0.0019 (8)
C90.0215 (10)0.0220 (10)0.0177 (9)0.0039 (8)0.0036 (7)0.0035 (8)
C100.0332 (12)0.0309 (12)0.0227 (10)0.0019 (10)0.0091 (9)0.0002 (9)
C110.0301 (11)0.0341 (12)0.0205 (10)0.0031 (10)0.0062 (9)0.0009 (9)
C120.0282 (11)0.0333 (12)0.0202 (10)0.0039 (9)0.0068 (8)0.0048 (9)
C130.0321 (12)0.0363 (13)0.0180 (10)0.0051 (10)0.0092 (9)0.0038 (9)
C140.0268 (11)0.0309 (12)0.0159 (9)0.0002 (9)0.0022 (8)0.0038 (8)
C150.0227 (10)0.0260 (11)0.0198 (10)0.0003 (8)0.0048 (8)0.0024 (8)
C160.0309 (11)0.0247 (11)0.0158 (9)0.0013 (9)0.0058 (8)0.0007 (8)
C170.0295 (11)0.0345 (12)0.0164 (9)0.0051 (10)0.0026 (8)0.0049 (9)
C180.0262 (11)0.0350 (12)0.0176 (9)0.0039 (9)0.0072 (8)0.0021 (8)
C190.0454 (15)0.067 (2)0.0277 (12)0.0281 (14)0.0179 (11)0.0136 (12)
C200.0231 (10)0.0244 (10)0.0124 (8)0.0029 (8)0.0037 (7)0.0015 (7)
C210.0253 (11)0.0244 (11)0.0199 (10)0.0037 (9)0.0038 (8)0.0005 (8)
C220.0198 (10)0.0296 (12)0.0256 (10)0.0023 (9)0.0041 (8)0.0030 (9)
C230.0233 (10)0.0267 (11)0.0170 (9)0.0031 (8)0.0035 (8)0.0032 (8)
C240.0244 (10)0.0239 (11)0.0150 (9)0.0023 (8)0.0035 (7)0.0009 (8)
C250.0196 (9)0.0287 (11)0.0136 (8)0.0022 (8)0.0035 (7)0.0004 (8)
C260.0332 (12)0.0268 (12)0.0348 (12)0.0053 (10)0.0072 (10)0.0092 (10)
O1W0.0332 (10)0.0396 (12)0.0434 (11)0.0009 (8)0.0048 (8)0.0090 (9)
Geometric parameters (Å, º) top
S1—O31.4504 (16)C12—C131.396 (3)
S1—O21.4557 (18)C12—C171.404 (3)
S1—O41.4562 (16)C13—C141.370 (3)
S1—C201.773 (2)C13—H13A0.9300
O1—C151.367 (3)C14—C151.396 (3)
O1—C191.422 (3)C14—H14A0.9300
O5—C231.366 (3)C15—C161.395 (3)
O5—C261.432 (3)C16—C171.384 (3)
N1—C91.360 (2)C16—H16A0.9300
N1—C11.396 (3)C17—H17A0.9300
N1—C181.485 (2)C18—H18A0.9600
C1—C21.406 (3)C18—H18B0.9600
C1—C61.415 (3)C18—H18C0.9600
C2—C31.367 (3)C19—H19A0.9600
C2—H2A0.9300C19—H19B0.9600
C3—C41.400 (3)C19—H19C0.9600
C3—H3A0.9300C20—C251.389 (3)
C4—C51.368 (3)C20—C211.396 (3)
C4—H4A0.9300C21—C221.382 (3)
C5—C61.421 (3)C21—H21A0.9300
C5—H5A0.9300C22—C231.396 (3)
C6—C71.419 (3)C22—H22A0.9300
C7—C81.353 (3)C23—C241.393 (3)
C7—H7A0.9300C24—C251.390 (3)
C8—C91.418 (3)C24—H24A0.9300
C8—H8A0.9300C25—H25A0.9300
C9—C101.442 (3)C26—H26A0.9600
C10—C111.348 (3)C26—H26B0.9600
C10—H10A0.9300C26—H26C0.9600
C11—C121.461 (3)O1W—H2W10.90 (4)
C11—H11A0.9300O1W—H1W10.89 (4)
O3—S1—O2113.22 (12)C13—C14—C15120.07 (19)
O3—S1—O4111.70 (10)C13—C14—H14A120.0
O2—S1—O4113.38 (11)C15—C14—H14A120.0
O3—S1—C20106.79 (9)O1—C15—C16124.49 (19)
O2—S1—C20105.17 (10)O1—C15—C14115.36 (18)
O4—S1—C20105.84 (10)C16—C15—C14120.1 (2)
C15—O1—C19117.35 (17)C17—C16—C15119.12 (19)
C23—O5—C26117.12 (17)C17—C16—H16A120.4
C9—N1—C1121.99 (17)C15—C16—H16A120.4
C9—N1—C18121.48 (17)C16—C17—C12121.22 (19)
C1—N1—C18116.52 (16)C16—C17—H17A119.4
N1—C1—C2121.25 (18)C12—C17—H17A119.4
N1—C1—C6118.99 (18)N1—C18—H18A109.5
C2—C1—C6119.76 (19)N1—C18—H18B109.5
C3—C2—C1119.7 (2)H18A—C18—H18B109.5
C3—C2—H2A120.2N1—C18—H18C109.5
C1—C2—H2A120.2H18A—C18—H18C109.5
C2—C3—C4121.2 (2)H18B—C18—H18C109.5
C2—C3—H3A119.4O1—C19—H19A109.5
C4—C3—H3A119.4O1—C19—H19B109.5
C5—C4—C3120.4 (2)H19A—C19—H19B109.5
C5—C4—H4A119.8O1—C19—H19C109.5
C3—C4—H4A119.8H19A—C19—H19C109.5
C4—C5—C6119.9 (2)H19B—C19—H19C109.5
C4—C5—H5A120.0C25—C20—C21119.31 (19)
C6—C5—H5A120.0C25—C20—S1120.90 (16)
C1—C6—C7118.76 (19)C21—C20—S1119.79 (17)
C1—C6—C5118.96 (19)C22—C21—C20120.2 (2)
C7—C6—C5122.28 (19)C22—C21—H21A119.9
C8—C7—C6119.94 (19)C20—C21—H21A119.9
C8—C7—H7A120.0C21—C22—C23120.1 (2)
C6—C7—H7A120.0C21—C22—H22A119.9
C7—C8—C9121.67 (19)C23—C22—H22A119.9
C7—C8—H8A119.2O5—C23—C24124.9 (2)
C9—C8—H8A119.2O5—C23—C22115.00 (19)
N1—C9—C8118.35 (19)C24—C23—C22120.1 (2)
N1—C9—C10120.78 (18)C25—C24—C23119.2 (2)
C8—C9—C10120.84 (19)C25—C24—H24A120.4
C11—C10—C9124.5 (2)C23—C24—H24A120.4
C11—C10—H10A117.7C20—C25—C24121.04 (19)
C9—C10—H10A117.7C20—C25—H25A119.5
C10—C11—C12124.7 (2)C24—C25—H25A119.5
C10—C11—H11A117.6O5—C26—H26A109.5
C12—C11—H11A117.6O5—C26—H26B109.5
C13—C12—C17118.3 (2)H26A—C26—H26B109.5
C13—C12—C11118.6 (2)O5—C26—H26C109.5
C17—C12—C11123.1 (2)H26A—C26—H26C109.5
C14—C13—C12121.1 (2)H26B—C26—H26C109.5
C14—C13—H13A119.5H2W1—O1W—H1W1106 (3)
C12—C13—H13A119.5
C9—N1—C1—C2174.1 (2)C11—C12—C13—C14175.3 (2)
C18—N1—C1—C27.4 (3)C12—C13—C14—C150.5 (4)
C9—N1—C1—C66.4 (3)C19—O1—C15—C161.1 (3)
C18—N1—C1—C6172.18 (19)C19—O1—C15—C14178.9 (2)
N1—C1—C2—C3178.4 (2)C13—C14—C15—O1177.7 (2)
C6—C1—C2—C31.1 (3)C13—C14—C15—C162.3 (3)
C1—C2—C3—C40.7 (4)O1—C15—C16—C17178.6 (2)
C2—C3—C4—C51.3 (4)C14—C15—C16—C171.4 (3)
C3—C4—C5—C60.0 (4)C15—C16—C17—C121.3 (3)
N1—C1—C6—C72.6 (3)C13—C12—C17—C163.1 (4)
C2—C1—C6—C7177.9 (2)C11—C12—C17—C16174.2 (2)
N1—C1—C6—C5177.18 (19)O3—S1—C20—C2579.63 (18)
C2—C1—C6—C52.4 (3)O2—S1—C20—C25159.81 (17)
C4—C5—C6—C11.8 (3)O4—S1—C20—C2539.52 (18)
C4—C5—C6—C7178.5 (2)O3—S1—C20—C2199.09 (17)
C1—C6—C7—C81.9 (3)O2—S1—C20—C2121.48 (19)
C5—C6—C7—C8178.3 (2)O4—S1—C20—C21141.76 (16)
C6—C7—C8—C92.9 (3)C25—C20—C21—C221.2 (3)
C1—N1—C9—C85.5 (3)S1—C20—C21—C22177.56 (15)
C18—N1—C9—C8173.04 (19)C20—C21—C22—C230.4 (3)
C1—N1—C9—C10176.50 (19)C26—O5—C23—C246.1 (3)
C18—N1—C9—C105.0 (3)C26—O5—C23—C22174.22 (19)
C7—C8—C9—N10.7 (3)C21—C22—C23—O5179.24 (18)
C7—C8—C9—C10178.8 (2)C21—C22—C23—C240.4 (3)
N1—C9—C10—C11172.5 (2)O5—C23—C24—C25179.13 (18)
C8—C9—C10—C115.5 (4)C22—C23—C24—C250.5 (3)
C9—C10—C11—C12179.6 (2)C21—C20—C25—C241.1 (3)
C10—C11—C12—C13176.6 (2)S1—C20—C25—C24177.61 (14)
C10—C11—C12—C176.1 (4)C23—C24—C25—C200.3 (3)
C17—C12—C13—C142.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O2i0.89 (4)2.58 (4)3.116 (3)120 (3)
O1W—H1W1···O3i0.89 (4)2.27 (4)3.162 (3)179 (3)
O1W—H2W1···O4ii0.90 (4)1.99 (4)2.860 (3)163 (4)
C5—H5A···O2iii0.932.423.245 (3)148
C7—H7A···O1Wiv0.932.583.371 (3)143
C11—H11A···O3v0.932.473.373 (3)163
C17—H17A···O4ii0.932.373.281 (3)165
C18—H18A···O4ii0.962.453.289 (3)147
C21—H21A···O20.932.532.895 (3)104
C26—H26A···O1vi0.962.573.307 (3)134
C2—H2A···Cg10.932.883.673 (2)144
C16—H16A···Cg1ii0.932.903.793 (2)161
Symmetry codes: (i) x, y+1, z; (ii) x, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x, y+3/2, z1/2; (v) x, y+1, z; (vi) x+1, y+5/2, z+1/2.
 

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