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The title compound, C19H18NO2+.0.59 C l·0.41I·H2O, exhibits second-order non-linear optical properties. The cations are essentially planar and they are linked with water mol­ecules through O—H...O hydrogen bonds, and the water mol­ecules are linked with Cl ions by O—H...Cl hydrogen bonds, forming infinite chains of chloride salts along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032569/tk2070sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032569/tk2070Isup2.hkl
Contains datablock I

CCDC reference: 621513

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.048
  • wR factor = 0.125
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.07
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT410_ALERT_2_C Short Intra H...H Contact H8 .. H11 .. 1.97 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10 .. H19A .. 1.82 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 3964 Count of symmetry unique reflns 2117 Completeness (_total/calc) 187.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1847 Fraction of Friedel pairs measured 0.872 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 5 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-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1-methylquinolinium 0.59-chloride 0.41-iodide monohydrate top
Crystal data top
C19H18NO2+·0.59Cl·0.41I·H2OZ = 1
Mr = 383.49F(000) = 197
Triclinic, P1Dx = 1.449 Mg m3
Hall symbol: P 1Melting point = 478–480 K
a = 6.2645 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2382 (8) ÅCell parameters from 3964 reflections
c = 9.1458 (8) Åθ = 2.4–28.0°
α = 68.743 (2)°µ = 0.89 mm1
β = 88.273 (1)°T = 153 K
γ = 87.467 (1)°Needle, colorless
V = 439.41 (7) Å30.52 × 0.11 × 0.10 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3964 independent reflections
Radiation source: fine-focus sealed tube3677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 2.4°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.661, Tmax = 0.920l = 1112
6398 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0738P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.003
3964 reflectionsΔρmax = 1.14 e Å3
224 parametersΔρmin = 0.28 e Å3
3 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (3)
Special details top

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*/UeqOcc. (<1)
I10.8955 (9)0.5782 (6)0.0877 (7)0.0560 (7)0.412 (4)
Cl10.896 (3)0.607 (2)0.088 (3)0.0560 (7)0.588 (4)
O11.4583 (5)0.9645 (4)0.6709 (4)0.0602 (8)
H11.41180.93210.76130.090*
O21.5650 (5)1.0451 (4)0.3797 (4)0.0607 (8)
N10.3853 (5)0.4280 (4)0.5550 (4)0.0423 (6)
C10.2078 (5)0.3354 (4)0.6272 (5)0.0431 (8)
C20.0649 (6)0.2697 (5)0.5464 (6)0.0542 (9)
H20.08550.29110.44000.065*
C30.1024 (7)0.1752 (5)0.6258 (7)0.0614 (11)
H30.19420.13130.57230.074*
C40.1396 (8)0.1430 (6)0.7800 (8)0.0715 (14)
H40.25460.07670.83100.086*
C50.0081 (8)0.2078 (7)0.8613 (7)0.0676 (12)
H50.03520.18630.96710.081*
C60.1677 (6)0.3067 (5)0.7856 (5)0.0511 (9)
C70.3063 (7)0.3765 (6)0.8645 (5)0.0551 (9)
H70.28150.35820.97000.066*
C80.4741 (6)0.4692 (5)0.7889 (5)0.0513 (8)
H80.56230.51640.84210.062*
C90.5174 (5)0.4954 (4)0.6303 (5)0.0400 (7)
C100.6988 (6)0.5938 (5)0.5506 (5)0.0473 (8)
H100.72200.61000.44540.057*
C110.8350 (6)0.6628 (5)0.6189 (5)0.0466 (8)
H110.80820.64570.72390.056*
C121.0210 (6)0.7619 (4)0.5463 (5)0.0450 (8)
C131.0780 (6)0.8027 (5)0.3928 (5)0.0515 (8)
H130.99600.76580.32840.062*
C141.2587 (7)0.8994 (5)0.3311 (5)0.0550 (9)
H141.29500.92830.22550.066*
C151.3839 (6)0.9524 (4)0.4265 (5)0.0461 (8)
C161.3304 (6)0.9097 (4)0.5823 (5)0.0448 (8)
C171.1497 (6)0.8165 (5)0.6407 (5)0.0457 (8)
H171.11230.78910.74590.055*
C181.6353 (10)1.0837 (8)0.2236 (7)0.0815 (16)
H18A1.76341.14840.20540.122*
H18B1.52641.15180.15360.122*
H18C1.66400.97710.20520.122*
C190.4269 (8)0.4478 (7)0.3924 (6)0.0606 (10)
H19A0.57300.47760.36540.091*
H19B0.33410.53850.32560.091*
H19C0.40090.34020.37870.091*
O1W1.3953 (7)0.8212 (6)0.0191 (5)0.0828 (11)
H1W11.50360.78890.03960.124*
H2W11.29080.76150.03000.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0526 (2)0.077 (2)0.0433 (2)0.0192 (12)0.00621 (13)0.0260 (12)
Cl10.0526 (2)0.077 (2)0.0433 (2)0.0192 (12)0.00621 (13)0.0260 (12)
O10.0519 (15)0.0741 (17)0.0598 (18)0.0290 (13)0.0040 (13)0.0278 (15)
O20.0560 (16)0.0617 (15)0.0603 (18)0.0233 (13)0.0126 (13)0.0159 (13)
N10.0360 (13)0.0441 (13)0.0502 (17)0.0029 (10)0.0009 (11)0.0212 (12)
C10.0314 (14)0.0361 (14)0.060 (2)0.0026 (11)0.0003 (13)0.0150 (14)
C20.0445 (18)0.0504 (18)0.075 (3)0.0045 (15)0.0015 (17)0.0308 (18)
C30.0421 (18)0.050 (2)0.095 (4)0.0109 (15)0.000 (2)0.029 (2)
C40.048 (2)0.058 (2)0.100 (4)0.0172 (18)0.007 (2)0.018 (2)
C50.050 (2)0.070 (3)0.068 (3)0.0119 (19)0.010 (2)0.008 (2)
C60.0408 (17)0.0499 (18)0.058 (2)0.0018 (14)0.0006 (15)0.0140 (16)
C70.0467 (19)0.070 (2)0.045 (2)0.0044 (17)0.0012 (15)0.0161 (17)
C80.0419 (17)0.059 (2)0.055 (2)0.0052 (15)0.0023 (15)0.0224 (17)
C90.0318 (13)0.0413 (15)0.0490 (18)0.0003 (11)0.0053 (12)0.0189 (13)
C100.0386 (16)0.0486 (17)0.054 (2)0.0080 (13)0.0032 (14)0.0168 (15)
C110.0393 (16)0.0479 (17)0.055 (2)0.0058 (13)0.0005 (14)0.0214 (15)
C120.0372 (15)0.0406 (16)0.059 (2)0.0023 (12)0.0003 (14)0.0197 (15)
C130.0456 (18)0.0547 (19)0.056 (2)0.0062 (15)0.0065 (16)0.0213 (17)
C140.053 (2)0.061 (2)0.051 (2)0.0066 (17)0.0039 (16)0.0191 (18)
C150.0409 (16)0.0380 (15)0.054 (2)0.0044 (12)0.0027 (14)0.0105 (14)
C160.0363 (15)0.0436 (16)0.056 (2)0.0076 (12)0.0024 (14)0.0194 (15)
C170.0387 (16)0.0458 (16)0.054 (2)0.0071 (13)0.0019 (14)0.0186 (14)
C180.073 (3)0.088 (3)0.062 (3)0.026 (3)0.022 (2)0.002 (3)
C190.058 (2)0.080 (3)0.055 (2)0.0190 (19)0.0082 (18)0.037 (2)
O1W0.076 (2)0.113 (3)0.061 (2)0.018 (2)0.0047 (17)0.030 (2)
Geometric parameters (Å, º) top
O1—C161.356 (5)C9—C101.443 (5)
O1—H10.8200C10—C111.331 (5)
O2—C151.365 (4)C10—H100.9300
O2—C181.407 (6)C11—C121.453 (5)
N1—C91.349 (4)C11—H110.9300
N1—C11.386 (4)C12—C131.360 (6)
N1—C191.453 (5)C12—C171.397 (5)
C1—C61.397 (6)C13—C141.396 (6)
C1—C21.419 (5)C13—H130.9300
C2—C31.359 (6)C14—C151.383 (6)
C2—H20.9300C14—H140.9300
C3—C41.352 (8)C15—C161.373 (6)
C3—H30.9300C16—C171.379 (5)
C4—C51.371 (8)C17—H170.9300
C4—H40.9300C18—H18A0.9600
C5—C61.407 (6)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
C6—C71.410 (6)C19—H19A0.9600
C7—C81.345 (6)C19—H19B0.9600
C7—H70.9300C19—H19C0.9600
C8—C91.407 (6)O1W—H1W10.8500
C8—H80.9300O1W—H2W10.8500
C16—O1—H1109.5C10—C11—C12126.7 (4)
C15—O2—C18117.4 (4)C10—C11—H11116.6
C9—N1—C1122.7 (3)C12—C11—H11116.6
C9—N1—C19120.6 (3)C13—C12—C17118.4 (3)
C1—N1—C19116.8 (3)C13—C12—C11123.8 (4)
N1—C1—C6118.5 (3)C17—C12—C11117.8 (4)
N1—C1—C2122.6 (4)C12—C13—C14120.5 (4)
C6—C1—C2118.9 (3)C12—C13—H13119.7
C3—C2—C1119.5 (5)C14—C13—H13119.7
C3—C2—H2120.3C15—C14—C13120.2 (4)
C1—C2—H2120.3C15—C14—H14119.9
C4—C3—C2122.1 (4)C13—C14—H14119.9
C4—C3—H3118.9O2—C15—C16114.8 (4)
C2—C3—H3118.9O2—C15—C14125.3 (4)
C3—C4—C5120.1 (4)C16—C15—C14119.9 (3)
C3—C4—H4119.9O1—C16—C15117.7 (3)
C5—C4—H4119.9O1—C16—C17123.2 (4)
C4—C5—C6120.4 (5)C15—C16—C17119.1 (4)
C4—C5—H5119.8C16—C17—C12121.8 (4)
C6—C5—H5119.8C16—C17—H17119.1
C1—C6—C5119.0 (4)C12—C17—H17119.1
C1—C6—C7118.8 (3)O2—C18—H18A109.5
C5—C6—C7122.2 (4)O2—C18—H18B109.5
C8—C7—C6120.7 (4)H18A—C18—H18B109.5
C8—C7—H7119.6O2—C18—H18C109.5
C6—C7—H7119.6H18A—C18—H18C109.5
C7—C8—C9120.7 (4)H18B—C18—H18C109.5
C7—C8—H8119.7N1—C19—H19A109.5
C9—C8—H8119.7N1—C19—H19B109.5
N1—C9—C8118.6 (3)H19A—C19—H19B109.5
N1—C9—C10121.2 (3)N1—C19—H19C109.5
C8—C9—C10120.2 (3)H19A—C19—H19C109.5
C11—C10—C9123.8 (4)H19B—C19—H19C109.5
C11—C10—H10118.1H1W1—O1W—H2W1107.7
C9—C10—H10118.1
C9—N1—C1—C61.8 (4)C7—C8—C9—N11.0 (5)
C19—N1—C1—C6177.1 (3)C7—C8—C9—C10179.5 (4)
C9—N1—C1—C2177.8 (3)N1—C9—C10—C11179.7 (3)
C19—N1—C1—C23.3 (5)C8—C9—C10—C110.8 (5)
N1—C1—C2—C3178.0 (3)C9—C10—C11—C12179.6 (3)
C6—C1—C2—C32.5 (5)C10—C11—C12—C132.1 (6)
C1—C2—C3—C40.9 (6)C10—C11—C12—C17177.1 (3)
C2—C3—C4—C50.7 (7)C17—C12—C13—C141.1 (5)
C3—C4—C5—C60.7 (7)C11—C12—C13—C14179.7 (3)
N1—C1—C6—C5177.9 (3)C12—C13—C14—C151.1 (6)
C2—C1—C6—C52.5 (5)C18—O2—C15—C16176.3 (4)
N1—C1—C6—C71.4 (5)C18—O2—C15—C142.9 (6)
C2—C1—C6—C7178.1 (3)C13—C14—C15—O2179.1 (4)
C4—C5—C6—C11.0 (6)C13—C14—C15—C160.0 (6)
C4—C5—C6—C7179.7 (4)O2—C15—C16—O10.8 (5)
C1—C6—C7—C80.1 (6)C14—C15—C16—O1179.9 (3)
C5—C6—C7—C8179.4 (4)O2—C15—C16—C17179.8 (3)
C6—C7—C8—C91.3 (6)C14—C15—C16—C171.0 (5)
C1—N1—C9—C80.6 (4)O1—C16—C17—C12180.0 (3)
C19—N1—C9—C8178.3 (3)C15—C16—C17—C121.0 (5)
C1—N1—C9—C10178.9 (3)C13—C12—C17—C160.1 (5)
C19—N1—C9—C102.2 (5)C11—C12—C17—C16179.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.821.882.671 (5)161
O1W—H1W1···Cl1ii0.852.783.51 (2)145
O1W—H2W1···Cl10.852.783.59 (2)161
C3—H3···O1iii0.932.593.254 (6)129
C19—H19C···O2iv0.962.593.433 (7)146
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x2, y1, z; (iv) x1, y1, z.
 

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