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In the title compound, C
19H
18NO
+·I
−·0.5I
2, the I
2 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
CCDC reference: 643654
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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−·0.5I2 | Z = 2 |
Mr = 530.14 | F(000) = 506 |
Triclinic, P1 | Dx = 1.940 Mg m−3 |
Hall symbol: -P 1 | Melting point = 688–689 K |
a = 8.9003 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3287 (2) Å | Cell parameters from 4379 reflections |
c = 11.2288 (3) Å | θ = 2.1–28.0° |
α = 90.151 (1)° | µ = 3.47 mm−1 |
β = 108.486 (1)° | T = 100 K |
γ = 110.760 (1)° | Needle, blue |
V = 907.69 (4) Å3 | 0.60 × 0.09 × 0.05 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 4379 independent reflections |
Radiation source: fine-focus sealed tube | 3866 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 2.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.230, Tmax = 0.846 | l = −14→14 |
14250 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.055 | H-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 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.79 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | −0.07620 (2) | 0.042575 (15) | 0.578894 (15) | 0.02495 (6) | |
I2 | 0.75622 (2) | 0.140903 (15) | 0.770929 (15) | 0.02447 (6) | |
N1 | 0.5533 (3) | 0.37814 (19) | 0.39151 (19) | 0.0183 (4) | |
C1 | 0.4083 (3) | 0.3692 (2) | 0.2894 (2) | 0.0195 (5) | |
C2 | 0.2789 (3) | 0.2401 (2) | 0.2295 (2) | 0.0239 (5) | |
H2 | 0.2880 | 0.1574 | 0.2570 | 0.029* | |
C3 | 0.1394 (3) | 0.2365 (3) | 0.1302 (3) | 0.0263 (5) | |
H3A | 0.0547 | 0.1507 | 0.0902 | 0.032* | |
C4 | 0.1215 (3) | 0.3596 (3) | 0.0876 (2) | 0.0251 (5) | |
H4 | 0.0252 | 0.3553 | 0.0208 | 0.030* | |
C5 | 0.2464 (3) | 0.4858 (3) | 0.1450 (2) | 0.0229 (5) | |
H5 | 0.2351 | 0.5675 | 0.1167 | 0.027* | |
C6 | 0.3918 (3) | 0.4932 (2) | 0.2465 (2) | 0.0197 (5) | |
C7 | 0.5236 (3) | 0.6224 (2) | 0.3068 (2) | 0.0210 (5) | |
H7 | 0.5149 | 0.7053 | 0.2795 | 0.025* | |
C8 | 0.6619 (3) | 0.6261 (2) | 0.4036 (2) | 0.0214 (5) | |
H8 | 0.7480 | 0.7118 | 0.4420 | 0.026* | |
C9 | 0.6789 (3) | 0.5008 (2) | 0.4486 (2) | 0.0173 (4) | |
C10 | 0.8307 (3) | 0.5083 (2) | 0.5520 (2) | 0.0208 (5) | |
H10 | 0.8435 | 0.4250 | 0.5736 | 0.025* | |
C11 | 0.9522 (3) | 0.6267 (3) | 0.6173 (2) | 0.0226 (5) | |
H11 | 0.9355 | 0.7083 | 0.5941 | 0.027* | |
C12 | 1.1086 (3) | 0.6442 (3) | 0.7210 (2) | 0.0209 (5) | |
C13 | 1.2223 (3) | 0.7794 (3) | 0.7752 (2) | 0.0250 (5) | |
H13 | 1.1955 | 0.8547 | 0.7440 | 0.030* | |
C14 | 1.3725 (3) | 0.8047 (2) | 0.8734 (2) | 0.0237 (5) | |
H14 | 1.4461 | 0.8958 | 0.9077 | 0.028* | |
C15 | 1.4134 (3) | 0.6927 (2) | 0.9209 (2) | 0.0187 (5) | |
C16 | 1.3024 (3) | 0.5559 (2) | 0.8690 (2) | 0.0200 (5) | |
H16 | 1.3302 | 0.4811 | 0.9008 | 0.024* | |
C17 | 1.1513 (3) | 0.5316 (2) | 0.7707 (2) | 0.0210 (5) | |
H17 | 1.0772 | 0.4404 | 0.7370 | 0.025* | |
C18 | 1.6742 (4) | 0.8432 (3) | 1.0770 (3) | 0.0316 (6) | |
H18A | 1.7739 | 0.8379 | 1.1395 | 0.047* | |
H18B | 1.6191 | 0.8852 | 1.1171 | 0.047* | |
H18C | 1.7072 | 0.8986 | 1.0145 | 0.047* | |
C19 | 0.5624 (4) | 0.2459 (2) | 0.4376 (3) | 0.0277 (6) | |
H19A | 0.5929 | 0.1986 | 0.3808 | 0.042* | |
H19B | 0.4531 | 0.1874 | 0.4413 | 0.042* | |
H19C | 0.6470 | 0.2660 | 0.5206 | 0.042* | |
O1 | 1.5586 (2) | 0.70550 (17) | 1.01738 (17) | 0.0245 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02141 (9) | 0.02014 (8) | 0.02592 (9) | 0.00189 (7) | 0.00507 (7) | 0.00764 (6) |
I2 | 0.03129 (10) | 0.01704 (8) | 0.02334 (9) | 0.01104 (7) | 0.00477 (7) | 0.00106 (6) |
N1 | 0.0207 (10) | 0.0168 (9) | 0.0189 (10) | 0.0079 (8) | 0.0078 (9) | 0.0043 (7) |
C1 | 0.0210 (12) | 0.0259 (12) | 0.0162 (11) | 0.0121 (10) | 0.0085 (10) | 0.0031 (9) |
C2 | 0.0307 (14) | 0.0202 (11) | 0.0250 (13) | 0.0113 (11) | 0.0129 (12) | 0.0060 (9) |
C3 | 0.0223 (13) | 0.0230 (12) | 0.0271 (13) | 0.0007 (10) | 0.0088 (11) | −0.0033 (10) |
C4 | 0.0196 (13) | 0.0363 (14) | 0.0196 (12) | 0.0133 (11) | 0.0037 (11) | 0.0035 (10) |
C5 | 0.0305 (14) | 0.0248 (12) | 0.0215 (12) | 0.0161 (11) | 0.0129 (11) | 0.0073 (9) |
C6 | 0.0199 (12) | 0.0219 (11) | 0.0185 (11) | 0.0065 (10) | 0.0097 (10) | 0.0005 (9) |
C7 | 0.0246 (13) | 0.0188 (11) | 0.0234 (12) | 0.0097 (10) | 0.0112 (11) | 0.0057 (9) |
C8 | 0.0214 (12) | 0.0167 (10) | 0.0231 (12) | 0.0038 (10) | 0.0072 (11) | 0.0011 (9) |
C9 | 0.0174 (12) | 0.0199 (11) | 0.0172 (11) | 0.0080 (9) | 0.0080 (10) | 0.0022 (8) |
C10 | 0.0195 (12) | 0.0214 (11) | 0.0225 (12) | 0.0087 (10) | 0.0073 (11) | 0.0038 (9) |
C11 | 0.0238 (13) | 0.0239 (12) | 0.0224 (12) | 0.0118 (10) | 0.0077 (11) | 0.0070 (9) |
C12 | 0.0201 (12) | 0.0255 (12) | 0.0189 (12) | 0.0090 (10) | 0.0085 (10) | 0.0047 (9) |
C13 | 0.0278 (14) | 0.0235 (12) | 0.0252 (13) | 0.0143 (11) | 0.0058 (11) | 0.0069 (10) |
C14 | 0.0262 (14) | 0.0194 (11) | 0.0242 (12) | 0.0100 (10) | 0.0052 (11) | 0.0041 (9) |
C15 | 0.0195 (12) | 0.0226 (11) | 0.0148 (11) | 0.0099 (10) | 0.0047 (10) | 0.0033 (9) |
C16 | 0.0235 (13) | 0.0207 (11) | 0.0188 (11) | 0.0104 (10) | 0.0086 (10) | 0.0051 (9) |
C17 | 0.0209 (12) | 0.0194 (11) | 0.0211 (12) | 0.0042 (10) | 0.0090 (10) | 0.0010 (9) |
C18 | 0.0280 (15) | 0.0291 (13) | 0.0264 (14) | 0.0076 (12) | −0.0018 (12) | −0.0023 (11) |
C19 | 0.0330 (15) | 0.0173 (11) | 0.0275 (13) | 0.0086 (11) | 0.0043 (12) | 0.0058 (10) |
O1 | 0.0212 (9) | 0.0227 (8) | 0.0229 (9) | 0.0086 (7) | −0.0016 (8) | 0.0014 (7) |
Geometric parameters (Å, º) top
I1—I1i | 2.8485 (4) | C10—H10 | 0.9300 |
N1—C9 | 1.343 (3) | C11—C12 | 1.455 (4) |
N1—C1 | 1.402 (3) | C11—H11 | 0.9300 |
N1—C19 | 1.482 (3) | C12—C13 | 1.396 (4) |
C1—C2 | 1.405 (3) | C12—C17 | 1.411 (3) |
C1—C6 | 1.409 (3) | C13—C14 | 1.374 (4) |
C2—C3 | 1.369 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.390 (3) |
C3—C4 | 1.404 (4) | C14—H14 | 0.9300 |
C3—H3A | 0.9300 | C15—O1 | 1.361 (3) |
C4—C5 | 1.365 (4) | C15—C16 | 1.398 (3) |
C4—H4 | 0.9300 | C16—C17 | 1.381 (4) |
C5—C6 | 1.405 (4) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.414 (3) | C18—O1 | 1.432 (3) |
C7—C8 | 1.348 (4) | C18—H18A | 0.9600 |
C7—H7 | 0.9300 | C18—H18B | 0.9600 |
C8—C9 | 1.431 (3) | C18—H18C | 0.9600 |
C8—H8 | 0.9300 | C19—H19A | 0.9600 |
C9—C10 | 1.452 (3) | C19—H19B | 0.9600 |
C10—C11 | 1.326 (4) | C19—H19C | 0.9600 |
| | | |
C9—N1—C1 | 122.30 (19) | C10—C11—H11 | 116.1 |
C9—N1—C19 | 120.3 (2) | C12—C11—H11 | 116.1 |
C1—N1—C19 | 117.4 (2) | C13—C12—C17 | 118.0 (2) |
N1—C1—C2 | 121.7 (2) | C13—C12—C11 | 118.5 (2) |
N1—C1—C6 | 119.0 (2) | C17—C12—C11 | 123.5 (2) |
C2—C1—C6 | 119.3 (2) | C14—C13—C12 | 122.0 (2) |
C3—C2—C1 | 119.7 (2) | C14—C13—H13 | 119.0 |
C3—C2—H2 | 120.2 | C12—C13—H13 | 119.0 |
C1—C2—H2 | 120.2 | C13—C14—C15 | 119.4 (2) |
C2—C3—C4 | 121.4 (2) | C13—C14—H14 | 120.3 |
C2—C3—H3A | 119.3 | C15—C14—H14 | 120.3 |
C4—C3—H3A | 119.3 | O1—C15—C14 | 124.4 (2) |
C5—C4—C3 | 119.6 (2) | O1—C15—C16 | 115.5 (2) |
C5—C4—H4 | 120.2 | C14—C15—C16 | 120.1 (2) |
C3—C4—H4 | 120.2 | C17—C16—C15 | 120.0 (2) |
C4—C5—C6 | 120.5 (2) | C17—C16—H16 | 120.0 |
C4—C5—H5 | 119.8 | C15—C16—H16 | 120.0 |
C6—C5—H5 | 119.8 | C16—C17—C12 | 120.5 (2) |
C5—C6—C1 | 119.6 (2) | C16—C17—H17 | 119.8 |
C5—C6—C7 | 121.6 (2) | C12—C17—H17 | 119.8 |
C1—C6—C7 | 118.8 (2) | O1—C18—H18A | 109.5 |
C8—C7—C6 | 120.2 (2) | O1—C18—H18B | 109.5 |
C8—C7—H7 | 119.9 | H18A—C18—H18B | 109.5 |
C6—C7—H7 | 119.9 | O1—C18—H18C | 109.5 |
C7—C8—C9 | 121.4 (2) | H18A—C18—H18C | 109.5 |
C7—C8—H8 | 119.3 | H18B—C18—H18C | 109.5 |
C9—C8—H8 | 119.3 | N1—C19—H19A | 109.5 |
N1—C9—C8 | 118.3 (2) | N1—C19—H19B | 109.5 |
N1—C9—C10 | 121.7 (2) | H19A—C19—H19B | 109.5 |
C8—C9—C10 | 120.0 (2) | N1—C19—H19C | 109.5 |
C11—C10—C9 | 124.0 (2) | H19A—C19—H19C | 109.5 |
C11—C10—H10 | 118.0 | H19B—C19—H19C | 109.5 |
C9—C10—H10 | 118.0 | C15—O1—C18 | 117.90 (19) |
C10—C11—C12 | 127.7 (2) | | |
| | | |
C9—N1—C1—C2 | 179.1 (2) | C19—N1—C9—C10 | 3.3 (3) |
C19—N1—C1—C2 | −2.3 (3) | C7—C8—C9—N1 | 0.2 (4) |
C9—N1—C1—C6 | −1.2 (3) | C7—C8—C9—C10 | 179.1 (2) |
C19—N1—C1—C6 | 177.3 (2) | N1—C9—C10—C11 | −174.9 (2) |
N1—C1—C2—C3 | 179.9 (2) | C8—C9—C10—C11 | 6.2 (4) |
C6—C1—C2—C3 | 0.2 (4) | C9—C10—C11—C12 | −179.4 (2) |
C1—C2—C3—C4 | −0.7 (4) | C10—C11—C12—C13 | 178.5 (3) |
C2—C3—C4—C5 | 0.8 (4) | C10—C11—C12—C17 | −2.1 (4) |
C3—C4—C5—C6 | −0.3 (4) | C17—C12—C13—C14 | 0.5 (4) |
C4—C5—C6—C1 | −0.1 (4) | C11—C12—C13—C14 | 180.0 (2) |
C4—C5—C6—C7 | 179.4 (2) | C12—C13—C14—C15 | −0.1 (4) |
N1—C1—C6—C5 | −179.5 (2) | C13—C14—C15—O1 | 179.8 (2) |
C2—C1—C6—C5 | 0.2 (3) | C13—C14—C15—C16 | −0.1 (4) |
N1—C1—C6—C7 | 1.0 (3) | O1—C15—C16—C17 | 179.9 (2) |
C2—C1—C6—C7 | −179.4 (2) | C14—C15—C16—C17 | −0.2 (4) |
C5—C6—C7—C8 | −179.7 (2) | C15—C16—C17—C12 | 0.6 (4) |
C1—C6—C7—C8 | −0.2 (4) | C13—C12—C17—C16 | −0.8 (4) |
C6—C7—C8—C9 | −0.4 (4) | C11—C12—C17—C16 | 179.8 (2) |
C1—N1—C9—C8 | 0.6 (3) | C14—C15—O1—C18 | 2.3 (4) |
C19—N1—C9—C8 | −177.9 (2) | C16—C15—O1—C18 | −177.9 (2) |
C1—N1—C9—C10 | −178.2 (2) | | |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···I2ii | 0.93 | 2.97 | 3.835 (2) | 156 |
C16—H16···O1iii | 0.93 | 2.52 | 3.440 (3) | 173 |
C19—H19A···Cg3iv | 0.96 | 3.06 | 3.392 (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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