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In the title compound, C19H18NO+·I·0.5I2, the I2 mol­ecule lies on a crystallographic center of symmetry and the cation is essentially planar and in an E configuration. The dihedral angle between the quinolinium and benzene ring systems is 4.06 (10)°. In the crystal structure, the cations are packed in an anti­parallel fashion along the a axis and weak C—H...O and C—H...I inter­actions link the components of the structure into a three-dimensional network. Weak C—H...π inter­actions are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010859/lh2324sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010859/lh2324Isup2.hkl
Contains datablock I

CCDC reference: 643654

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.022
  • wR factor = 0.055
  • Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT431_ALERT_2_A Short Inter HL..A Contact I1 .. I2 .. 3.32 Ang.
Author Response: I1 and I2 are separate entities. I2 is an anion whereas I1 is half of an I~2~ molecule. The distance between I1 and I2 is normal.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT410_ALERT_2_C Short Intra H...H Contact H8 .. H11 .. 1.98 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10 .. H19C .. 1.85 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 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 iodide hemiiodine top
Crystal data top
C19H18NO+·I·0.5I2Z = 2
Mr = 530.14F(000) = 506
Triclinic, P1Dx = 1.940 Mg m3
Hall symbol: -P 1Melting point = 688–689 K
a = 8.9003 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3287 (2) ÅCell parameters from 4379 reflections
c = 11.2288 (3) Åθ = 2.1–28.0°
α = 90.151 (1)°µ = 3.47 mm1
β = 108.486 (1)°T = 100 K
γ = 110.760 (1)°Needle, blue
V = 907.69 (4) Å30.60 × 0.09 × 0.05 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4379 independent reflections
Radiation source: fine-focus sealed tube3866 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 2.1°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1313
Tmin = 0.230, Tmax = 0.846l = 1414
14250 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)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0231P)2 + 0.5526P]
where P = (Fo2 + 2Fc2)/3
4379 reflections(Δ/σ)max = 0.002
211 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.79 e Å3
Special details top

Experimental. The 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
I10.07620 (2)0.042575 (15)0.578894 (15)0.02495 (6)
I20.75622 (2)0.140903 (15)0.770929 (15)0.02447 (6)
N10.5533 (3)0.37814 (19)0.39151 (19)0.0183 (4)
C10.4083 (3)0.3692 (2)0.2894 (2)0.0195 (5)
C20.2789 (3)0.2401 (2)0.2295 (2)0.0239 (5)
H20.28800.15740.25700.029*
C30.1394 (3)0.2365 (3)0.1302 (3)0.0263 (5)
H3A0.05470.15070.09020.032*
C40.1215 (3)0.3596 (3)0.0876 (2)0.0251 (5)
H40.02520.35530.02080.030*
C50.2464 (3)0.4858 (3)0.1450 (2)0.0229 (5)
H50.23510.56750.11670.027*
C60.3918 (3)0.4932 (2)0.2465 (2)0.0197 (5)
C70.5236 (3)0.6224 (2)0.3068 (2)0.0210 (5)
H70.51490.70530.27950.025*
C80.6619 (3)0.6261 (2)0.4036 (2)0.0214 (5)
H80.74800.71180.44200.026*
C90.6789 (3)0.5008 (2)0.4486 (2)0.0173 (4)
C100.8307 (3)0.5083 (2)0.5520 (2)0.0208 (5)
H100.84350.42500.57360.025*
C110.9522 (3)0.6267 (3)0.6173 (2)0.0226 (5)
H110.93550.70830.59410.027*
C121.1086 (3)0.6442 (3)0.7210 (2)0.0209 (5)
C131.2223 (3)0.7794 (3)0.7752 (2)0.0250 (5)
H131.19550.85470.74400.030*
C141.3725 (3)0.8047 (2)0.8734 (2)0.0237 (5)
H141.44610.89580.90770.028*
C151.4134 (3)0.6927 (2)0.9209 (2)0.0187 (5)
C161.3024 (3)0.5559 (2)0.8690 (2)0.0200 (5)
H161.33020.48110.90080.024*
C171.1513 (3)0.5316 (2)0.7707 (2)0.0210 (5)
H171.07720.44040.73700.025*
C181.6742 (4)0.8432 (3)1.0770 (3)0.0316 (6)
H18A1.77390.83791.13950.047*
H18B1.61910.88521.11710.047*
H18C1.70720.89861.01450.047*
C190.5624 (4)0.2459 (2)0.4376 (3)0.0277 (6)
H19A0.59290.19860.38080.042*
H19B0.45310.18740.44130.042*
H19C0.64700.26600.52060.042*
O11.5586 (2)0.70550 (17)1.01738 (17)0.0245 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02141 (9)0.02014 (8)0.02592 (9)0.00189 (7)0.00507 (7)0.00764 (6)
I20.03129 (10)0.01704 (8)0.02334 (9)0.01104 (7)0.00477 (7)0.00106 (6)
N10.0207 (10)0.0168 (9)0.0189 (10)0.0079 (8)0.0078 (9)0.0043 (7)
C10.0210 (12)0.0259 (12)0.0162 (11)0.0121 (10)0.0085 (10)0.0031 (9)
C20.0307 (14)0.0202 (11)0.0250 (13)0.0113 (11)0.0129 (12)0.0060 (9)
C30.0223 (13)0.0230 (12)0.0271 (13)0.0007 (10)0.0088 (11)0.0033 (10)
C40.0196 (13)0.0363 (14)0.0196 (12)0.0133 (11)0.0037 (11)0.0035 (10)
C50.0305 (14)0.0248 (12)0.0215 (12)0.0161 (11)0.0129 (11)0.0073 (9)
C60.0199 (12)0.0219 (11)0.0185 (11)0.0065 (10)0.0097 (10)0.0005 (9)
C70.0246 (13)0.0188 (11)0.0234 (12)0.0097 (10)0.0112 (11)0.0057 (9)
C80.0214 (12)0.0167 (10)0.0231 (12)0.0038 (10)0.0072 (11)0.0011 (9)
C90.0174 (12)0.0199 (11)0.0172 (11)0.0080 (9)0.0080 (10)0.0022 (8)
C100.0195 (12)0.0214 (11)0.0225 (12)0.0087 (10)0.0073 (11)0.0038 (9)
C110.0238 (13)0.0239 (12)0.0224 (12)0.0118 (10)0.0077 (11)0.0070 (9)
C120.0201 (12)0.0255 (12)0.0189 (12)0.0090 (10)0.0085 (10)0.0047 (9)
C130.0278 (14)0.0235 (12)0.0252 (13)0.0143 (11)0.0058 (11)0.0069 (10)
C140.0262 (14)0.0194 (11)0.0242 (12)0.0100 (10)0.0052 (11)0.0041 (9)
C150.0195 (12)0.0226 (11)0.0148 (11)0.0099 (10)0.0047 (10)0.0033 (9)
C160.0235 (13)0.0207 (11)0.0188 (11)0.0104 (10)0.0086 (10)0.0051 (9)
C170.0209 (12)0.0194 (11)0.0211 (12)0.0042 (10)0.0090 (10)0.0010 (9)
C180.0280 (15)0.0291 (13)0.0264 (14)0.0076 (12)0.0018 (12)0.0023 (11)
C190.0330 (15)0.0173 (11)0.0275 (13)0.0086 (11)0.0043 (12)0.0058 (10)
O10.0212 (9)0.0227 (8)0.0229 (9)0.0086 (7)0.0016 (8)0.0014 (7)
Geometric parameters (Å, º) top
I1—I1i2.8485 (4)C10—H100.9300
N1—C91.343 (3)C11—C121.455 (4)
N1—C11.402 (3)C11—H110.9300
N1—C191.482 (3)C12—C131.396 (4)
C1—C21.405 (3)C12—C171.411 (3)
C1—C61.409 (3)C13—C141.374 (4)
C2—C31.369 (4)C13—H130.9300
C2—H20.9300C14—C151.390 (3)
C3—C41.404 (4)C14—H140.9300
C3—H3A0.9300C15—O11.361 (3)
C4—C51.365 (4)C15—C161.398 (3)
C4—H40.9300C16—C171.381 (4)
C5—C61.405 (4)C16—H160.9300
C5—H50.9300C17—H170.9300
C6—C71.414 (3)C18—O11.432 (3)
C7—C81.348 (4)C18—H18A0.9600
C7—H70.9300C18—H18B0.9600
C8—C91.431 (3)C18—H18C0.9600
C8—H80.9300C19—H19A0.9600
C9—C101.452 (3)C19—H19B0.9600
C10—C111.326 (4)C19—H19C0.9600
C9—N1—C1122.30 (19)C10—C11—H11116.1
C9—N1—C19120.3 (2)C12—C11—H11116.1
C1—N1—C19117.4 (2)C13—C12—C17118.0 (2)
N1—C1—C2121.7 (2)C13—C12—C11118.5 (2)
N1—C1—C6119.0 (2)C17—C12—C11123.5 (2)
C2—C1—C6119.3 (2)C14—C13—C12122.0 (2)
C3—C2—C1119.7 (2)C14—C13—H13119.0
C3—C2—H2120.2C12—C13—H13119.0
C1—C2—H2120.2C13—C14—C15119.4 (2)
C2—C3—C4121.4 (2)C13—C14—H14120.3
C2—C3—H3A119.3C15—C14—H14120.3
C4—C3—H3A119.3O1—C15—C14124.4 (2)
C5—C4—C3119.6 (2)O1—C15—C16115.5 (2)
C5—C4—H4120.2C14—C15—C16120.1 (2)
C3—C4—H4120.2C17—C16—C15120.0 (2)
C4—C5—C6120.5 (2)C17—C16—H16120.0
C4—C5—H5119.8C15—C16—H16120.0
C6—C5—H5119.8C16—C17—C12120.5 (2)
C5—C6—C1119.6 (2)C16—C17—H17119.8
C5—C6—C7121.6 (2)C12—C17—H17119.8
C1—C6—C7118.8 (2)O1—C18—H18A109.5
C8—C7—C6120.2 (2)O1—C18—H18B109.5
C8—C7—H7119.9H18A—C18—H18B109.5
C6—C7—H7119.9O1—C18—H18C109.5
C7—C8—C9121.4 (2)H18A—C18—H18C109.5
C7—C8—H8119.3H18B—C18—H18C109.5
C9—C8—H8119.3N1—C19—H19A109.5
N1—C9—C8118.3 (2)N1—C19—H19B109.5
N1—C9—C10121.7 (2)H19A—C19—H19B109.5
C8—C9—C10120.0 (2)N1—C19—H19C109.5
C11—C10—C9124.0 (2)H19A—C19—H19C109.5
C11—C10—H10118.0H19B—C19—H19C109.5
C9—C10—H10118.0C15—O1—C18117.90 (19)
C10—C11—C12127.7 (2)
C9—N1—C1—C2179.1 (2)C19—N1—C9—C103.3 (3)
C19—N1—C1—C22.3 (3)C7—C8—C9—N10.2 (4)
C9—N1—C1—C61.2 (3)C7—C8—C9—C10179.1 (2)
C19—N1—C1—C6177.3 (2)N1—C9—C10—C11174.9 (2)
N1—C1—C2—C3179.9 (2)C8—C9—C10—C116.2 (4)
C6—C1—C2—C30.2 (4)C9—C10—C11—C12179.4 (2)
C1—C2—C3—C40.7 (4)C10—C11—C12—C13178.5 (3)
C2—C3—C4—C50.8 (4)C10—C11—C12—C172.1 (4)
C3—C4—C5—C60.3 (4)C17—C12—C13—C140.5 (4)
C4—C5—C6—C10.1 (4)C11—C12—C13—C14180.0 (2)
C4—C5—C6—C7179.4 (2)C12—C13—C14—C150.1 (4)
N1—C1—C6—C5179.5 (2)C13—C14—C15—O1179.8 (2)
C2—C1—C6—C50.2 (3)C13—C14—C15—C160.1 (4)
N1—C1—C6—C71.0 (3)O1—C15—C16—C17179.9 (2)
C2—C1—C6—C7179.4 (2)C14—C15—C16—C170.2 (4)
C5—C6—C7—C8179.7 (2)C15—C16—C17—C120.6 (4)
C1—C6—C7—C80.2 (4)C13—C12—C17—C160.8 (4)
C6—C7—C8—C90.4 (4)C11—C12—C17—C16179.8 (2)
C1—N1—C9—C80.6 (3)C14—C15—O1—C182.3 (4)
C19—N1—C9—C8177.9 (2)C16—C15—O1—C18177.9 (2)
C1—N1—C9—C10178.2 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···I2ii0.932.973.835 (2)156
C16—H16···O1iii0.932.523.440 (3)173
C19—H19A···Cg3iv0.963.063.392 (3)125
Symmetry codes: (ii) x+1, y, z+1; (iii) x+3, y+1, z+2; (iv) x+2, y+1, z+1.
 

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