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In the title compound, C15H16NO2+·I, H2O, the cation is almost planar and exists in an E configuration. The dihedral angle between the pyridinium and benzene rings is 7.05 (5)°. In the crystal structure, water mol­ecules are linked to the cations and anions by O—H...O and O—H...I hydrogen bonds. These, together with weak C—H...O inter­actions, form a three-dimensional network. C—H...π inter­actions involving the benzene rings further stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013426/sj2258sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013426/sj2258Isup2.hkl
Contains datablock I

CCDC reference: 643660

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.020
  • wR factor = 0.048
  • Data-to-parameter ratio = 34.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 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 5 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 0 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 3 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).

4-[(E)-2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1-methylpyridinium iodide monohydrate top
Crystal data top
C15H16NO2+·I·H2OF(000) = 768
Mr = 387.20Dx = 1.688 Mg m3
Monoclinic, P21/cMelting point = 503–504 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.1791 (1) ÅCell parameters from 6694 reflections
b = 17.9508 (2) Åθ = 2.3–35.0°
c = 10.3967 (1) ŵ = 2.11 mm1
β = 93.320 (1)°T = 100 K
V = 1523.90 (3) Å3Block, yellow
Z = 40.56 × 0.20 × 0.17 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
6694 independent reflections
Radiation source: fine-focus sealed tube6189 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 2.3°
ω scansh = 1213
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2828
Tmin = 0.384, Tmax = 0.718l = 1616
36530 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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0207P)2 + 0.7057P]
where P = (Fo2 + 2Fc2)/3
6694 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.65 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
O10.74021 (12)0.60066 (4)0.85115 (9)0.01874 (16)
H1O10.67350.58470.79600.028*
O20.91209 (10)0.66689 (5)1.03812 (8)0.01518 (14)
N10.14456 (12)0.95263 (5)0.32872 (9)0.01432 (16)
C10.26146 (14)0.83525 (6)0.38319 (10)0.01450 (17)
H1A0.27300.78500.36400.017*
C20.16188 (14)0.87952 (6)0.30416 (11)0.01501 (18)
H2A0.10570.85860.23270.018*
C30.22325 (15)0.98395 (6)0.43309 (11)0.01643 (19)
H3A0.20981.03450.44930.020*
C40.32294 (14)0.94192 (6)0.51549 (11)0.01600 (19)
H4A0.37590.96420.58710.019*
C50.34579 (13)0.86529 (6)0.49254 (10)0.01302 (17)
C60.44619 (13)0.81734 (6)0.57730 (10)0.01395 (17)
H6A0.45470.76730.55530.017*
C70.52779 (13)0.84103 (6)0.68609 (10)0.01386 (17)
H7A0.52070.89150.70490.017*
C80.62585 (13)0.79545 (6)0.77713 (10)0.01265 (17)
C90.71472 (13)0.83032 (6)0.87881 (10)0.01438 (17)
H9A0.70770.88170.88800.017*
C100.81366 (13)0.78959 (6)0.96682 (10)0.01428 (17)
H10A0.87420.81401.03260.017*
C110.82191 (13)0.71245 (6)0.95630 (10)0.01277 (17)
C120.73012 (13)0.67624 (6)0.85545 (10)0.01287 (16)
C130.63494 (13)0.71726 (6)0.76691 (10)0.01316 (17)
H13A0.57630.69300.70000.016*
C140.03798 (15)0.99914 (7)0.24171 (12)0.0189 (2)
H14A0.04420.98190.15470.028*
H14B0.07361.05010.24750.028*
H14C0.07310.99570.26640.028*
C151.01407 (14)0.70287 (7)1.13665 (11)0.01629 (19)
H15A1.07780.66611.18410.024*
H15B0.94660.72921.19400.024*
H15C1.08600.73741.09760.024*
I10.254702 (9)0.609997 (4)0.462925 (7)0.01631 (2)
O1W0.52778 (13)0.52803 (5)0.69325 (9)0.02233 (18)
H1W0.578 (3)0.5000 (14)0.653 (2)0.048 (7)*
H2W0.468 (3)0.5460 (13)0.642 (2)0.041 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0259 (4)0.0110 (3)0.0183 (4)0.0014 (3)0.0071 (3)0.0005 (3)
O20.0159 (3)0.0145 (3)0.0145 (3)0.0007 (3)0.0041 (3)0.0015 (3)
N10.0163 (4)0.0136 (4)0.0129 (4)0.0023 (3)0.0006 (3)0.0010 (3)
C10.0178 (5)0.0119 (4)0.0136 (4)0.0008 (3)0.0004 (3)0.0000 (3)
C20.0177 (5)0.0139 (4)0.0132 (4)0.0003 (3)0.0006 (3)0.0001 (3)
C30.0201 (5)0.0129 (4)0.0158 (4)0.0021 (4)0.0024 (4)0.0008 (3)
C40.0194 (5)0.0125 (4)0.0156 (4)0.0018 (3)0.0030 (4)0.0012 (3)
C50.0137 (4)0.0122 (4)0.0132 (4)0.0007 (3)0.0007 (3)0.0008 (3)
C60.0149 (4)0.0124 (4)0.0146 (4)0.0018 (3)0.0003 (3)0.0011 (3)
C70.0147 (4)0.0124 (4)0.0144 (4)0.0016 (3)0.0002 (3)0.0008 (3)
C80.0129 (4)0.0123 (4)0.0128 (4)0.0002 (3)0.0006 (3)0.0011 (3)
C90.0154 (4)0.0123 (4)0.0153 (4)0.0002 (3)0.0005 (3)0.0003 (3)
C100.0145 (4)0.0143 (4)0.0139 (4)0.0010 (3)0.0010 (3)0.0004 (3)
C110.0119 (4)0.0144 (4)0.0119 (4)0.0004 (3)0.0003 (3)0.0011 (3)
C120.0144 (4)0.0112 (4)0.0129 (4)0.0004 (3)0.0003 (3)0.0005 (3)
C130.0142 (4)0.0128 (4)0.0123 (4)0.0002 (3)0.0005 (3)0.0004 (3)
C140.0211 (5)0.0169 (5)0.0181 (5)0.0038 (4)0.0035 (4)0.0036 (4)
C150.0149 (4)0.0194 (5)0.0142 (4)0.0001 (4)0.0026 (3)0.0000 (4)
I10.01665 (4)0.01634 (4)0.01573 (4)0.00059 (2)0.00087 (2)0.00089 (2)
O1W0.0291 (5)0.0183 (4)0.0187 (4)0.0049 (3)0.0065 (3)0.0037 (3)
Geometric parameters (Å, º) top
O1—C121.3600 (13)C7—H7A0.9300
O1—H1O10.8200C8—C91.3960 (15)
O2—C111.3653 (13)C8—C131.4098 (15)
O2—C151.4364 (13)C9—C101.3932 (15)
N1—C21.3461 (14)C9—H9A0.9300
N1—C31.3517 (14)C10—C111.3910 (15)
N1—C141.4777 (14)C10—H10A0.9300
C1—C21.3758 (15)C11—C121.4123 (14)
C1—C51.4029 (15)C12—C131.3830 (14)
C1—H1A0.9300C13—H13A0.9300
C2—H2A0.9300C14—H14A0.9600
C3—C41.3737 (15)C14—H14B0.9600
C3—H3A0.9300C14—H14C0.9600
C4—C51.4103 (15)C15—H15A0.9600
C4—H4A0.9300C15—H15B0.9600
C5—C61.4519 (15)C15—H15C0.9600
C6—C71.3483 (15)O1W—H1W0.79 (3)
C6—H6A0.9300O1W—H2W0.77 (2)
C7—C81.4562 (14)
C12—O1—H1O1109.5C10—C9—C8121.28 (10)
C11—O2—C15116.45 (9)C10—C9—H9A119.4
C2—N1—C3120.49 (9)C8—C9—H9A119.4
C2—N1—C14119.97 (9)C11—C10—C9119.99 (10)
C3—N1—C14119.54 (9)C11—C10—H10A120.0
C2—C1—C5120.54 (10)C9—C10—H10A120.0
C2—C1—H1A119.7O2—C11—C10125.05 (9)
C5—C1—H1A119.7O2—C11—C12115.57 (9)
N1—C2—C1121.01 (10)C10—C11—C12119.37 (9)
N1—C2—H2A119.5O1—C12—C13122.83 (9)
C1—C2—H2A119.5O1—C12—C11116.93 (9)
N1—C3—C4120.66 (10)C13—C12—C11120.24 (9)
N1—C3—H3A119.7C12—C13—C8120.67 (9)
C4—C3—H3A119.7C12—C13—H13A119.7
C3—C4—C5120.66 (10)C8—C13—H13A119.7
C3—C4—H4A119.7N1—C14—H14A109.5
C5—C4—H4A119.7N1—C14—H14B109.5
C1—C5—C4116.64 (9)H14A—C14—H14B109.5
C1—C5—C6119.88 (10)N1—C14—H14C109.5
C4—C5—C6123.46 (9)H14A—C14—H14C109.5
C7—C6—C5123.87 (10)H14B—C14—H14C109.5
C7—C6—H6A118.1O2—C15—H15A109.5
C5—C6—H6A118.1O2—C15—H15B109.5
C6—C7—C8126.53 (10)H15A—C15—H15B109.5
C6—C7—H7A116.7O2—C15—H15C109.5
C8—C7—H7A116.7H15A—C15—H15C109.5
C9—C8—C13118.43 (9)H15B—C15—H15C109.5
C9—C8—C7118.90 (9)H1W—O1W—H2W103 (2)
C13—C8—C7122.67 (9)
C3—N1—C2—C10.95 (18)C13—C8—C9—C101.58 (17)
C14—N1—C2—C1179.47 (11)C7—C8—C9—C10178.41 (10)
C5—C1—C2—N10.85 (18)C8—C9—C10—C111.70 (17)
C2—N1—C3—C40.37 (18)C15—O2—C11—C104.48 (16)
C14—N1—C3—C4179.96 (11)C15—O2—C11—C12176.33 (10)
N1—C3—C4—C50.29 (19)C9—C10—C11—O2178.76 (10)
C2—C1—C5—C40.18 (17)C9—C10—C11—C120.40 (17)
C2—C1—C5—C6177.99 (11)O2—C11—C12—O10.47 (15)
C3—C4—C5—C10.37 (17)C10—C11—C12—O1178.76 (10)
C3—C4—C5—C6178.48 (11)O2—C11—C12—C13179.79 (10)
C1—C5—C6—C7178.16 (11)C10—C11—C12—C130.97 (16)
C4—C5—C6—C70.11 (18)O1—C12—C13—C8178.64 (11)
C5—C6—C7—C8177.85 (11)C11—C12—C13—C81.08 (17)
C6—C7—C8—C9174.06 (11)C9—C8—C13—C120.19 (16)
C6—C7—C8—C135.93 (18)C7—C8—C13—C12179.80 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···I1i0.79 (2)2.72 (2)3.5036 (10)173 (2)
O1W—H2W···I10.77 (2)2.73 (2)3.5026 (10)179 (2)
O1—H1O1···O1W0.821.862.6614 (13)167
C3—H3A···O1ii0.932.413.0713 (14)128
C3—H3A···O2ii0.932.583.4839 (14)163
C14—H14C···O1iii0.962.503.2797 (15)138
C6—H6A···Cg1iv0.933.053.4821 (11)110
C15—H15B···Cg1v0.962.653.5565 (12)157
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1/2, z+3/2; (iii) x1, y+3/2, z1/2; (iv) x, y+3/2, z1/2; (v) x, y+3/2, z+1/2.
 

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