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The crystal structure of the title compound, C
17H
20NO
2+·Cl
−, contains one molecule in the asymmetric unit. Molecules are linked
via one C—H
O and two O—H
Cl hydrogen bonds. The molecule also contains one intramolecular O—H
O hydrogen bond.
Supporting information
CCDC reference: 227011
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.062
- Data-to-parameter ratio = 19.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C5 = 22.49 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 = 11.38 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C6 - C7 = 14.20 su
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg 89.41 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C8 = 6.63 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 = 6.54 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 = 5.24 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C17 H20 N O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
Cl
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
N-Butyl-4-[2-(3,4-dihydroxyphenyl)vinyl]pyridinium chloride
top
Crystal data top
C17H20NO2+·Cl− | F(000) = 648 |
Mr = 305.79 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 12413 reflections |
a = 7.6510 (3) Å | θ = 2.8–31.0° |
b = 8.6180 (3) Å | µ = 0.24 mm−1 |
c = 24.5243 (10) Å | T = 291 K |
β = 89.4079 (15)° | Plate, yellow |
V = 1616.96 (11) Å3 | 0.65 × 0.15 × 0.06 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 1185 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.080 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −9→9 |
367 frames via ω–rotation (Δω = 1°) and two times 20 s per frame
(five sets at different κ–angles) scans | k = −9→11 |
11432 measured reflections | l = −31→30 |
3684 independent 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | w = 1/[σ2(Fo2)-0.06P] where P = (Fo2 + 2Fc2)/3 |
3684 reflections | (Δ/σ)max = 0.001 |
193 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−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 | x | y | z | Uiso*/Ueq | |
Cl1 | 1.03059 (6) | 0.04042 (6) | 1.242258 (17) | 0.0670 (2) | |
O1 | 1.10895 (19) | 0.1267 (2) | 1.11857 (5) | 0.0828 (5) | |
H1 | 1.1160 | 0.1303 | 1.1519 | 0.124* | |
O2 | 1.28143 (18) | 0.32410 (17) | 1.18236 (5) | 0.0695 (5) | |
H2 | 1.3274 | 0.3949 | 1.1993 | 0.104* | |
N1 | 1.0442 (2) | 0.5107 (2) | 0.75875 (6) | 0.0539 (5) | |
C1 | 1.1313 (2) | 0.3691 (3) | 0.92161 (8) | 0.0600 (6) | |
H1A | 1.0839 | 0.2737 | 0.9316 | 0.072* | |
C2 | 1.2125 (2) | 0.4494 (3) | 0.95962 (7) | 0.0614 (6) | |
H2A | 1.2636 | 0.5418 | 0.9481 | 0.074* | |
C3 | 1.2327 (2) | 0.4122 (3) | 1.01719 (8) | 0.0560 (7) | |
C4 | 1.1614 (2) | 0.2807 (3) | 1.04139 (8) | 0.0590 (6) | |
H4 | 1.1004 | 0.2090 | 1.0206 | 0.071* | |
C5 | 1.1817 (3) | 0.2575 (3) | 1.09648 (9) | 0.0570 (6) | |
C6 | 1.2732 (3) | 0.3630 (3) | 1.12830 (8) | 0.0550 (6) | |
C7 | 1.3462 (2) | 0.4907 (3) | 1.10581 (8) | 0.0652 (7) | |
H7 | 1.4094 | 0.5603 | 1.1268 | 0.078* | |
C8 | 1.3239 (2) | 0.5152 (3) | 1.04979 (8) | 0.0657 (7) | |
H8 | 1.3719 | 0.6037 | 1.0339 | 0.079* | |
C9 | 1.1102 (2) | 0.4191 (3) | 0.86497 (8) | 0.0527 (6) | |
C10 | 1.0146 (2) | 0.3263 (3) | 0.82928 (8) | 0.0664 (7) | |
H10 | 0.9718 | 0.2307 | 0.8409 | 0.080* | |
C11 | 0.9840 (3) | 0.3760 (3) | 0.77729 (9) | 0.0662 (7) | |
H11 | 0.9189 | 0.3134 | 0.7542 | 0.079* | |
C12 | 1.1412 (2) | 0.6007 (2) | 0.79156 (8) | 0.0585 (6) | |
H12 | 1.1861 | 0.6939 | 0.7784 | 0.070* | |
C13 | 1.1746 (2) | 0.5568 (3) | 0.84404 (8) | 0.0584 (6) | |
H13 | 1.2418 | 0.6208 | 0.8660 | 0.070* | |
C14 | 1.0028 (2) | 0.5625 (2) | 0.70269 (7) | 0.0637 (7) | |
H14A | 1.0306 | 0.6718 | 0.6991 | 0.076* | |
H14B | 0.8784 | 0.5503 | 0.6967 | 0.076* | |
C15 | 1.1020 (2) | 0.4728 (2) | 0.65996 (7) | 0.0617 (6) | |
H15A | 1.0706 | 0.3640 | 0.6626 | 0.074* | |
H15B | 1.2263 | 0.4816 | 0.6668 | 0.074* | |
C16 | 1.0642 (2) | 0.5308 (3) | 0.60263 (7) | 0.0702 (7) | |
H16A | 0.9392 | 0.5269 | 0.5966 | 0.084* | |
H16B | 1.1010 | 0.6382 | 0.5995 | 0.084* | |
C17 | 1.1568 (3) | 0.4357 (3) | 0.55907 (7) | 0.1009 (9) | |
H17A | 1.2791 | 0.4296 | 0.5672 | 0.151* | |
H17B | 1.1418 | 0.4842 | 0.5242 | 0.151* | |
H17C | 1.1081 | 0.3331 | 0.5583 | 0.151* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0712 (3) | 0.0636 (5) | 0.0663 (3) | −0.0003 (3) | −0.0087 (2) | 0.0078 (3) |
O1 | 0.0954 (11) | 0.0886 (16) | 0.0645 (10) | −0.0064 (10) | −0.0096 (9) | −0.0045 (10) |
O2 | 0.0830 (11) | 0.0756 (14) | 0.0501 (8) | 0.0006 (8) | −0.0120 (7) | 0.0002 (8) |
N1 | 0.0604 (11) | 0.0519 (17) | 0.0497 (12) | 0.0073 (10) | −0.0071 (9) | −0.0032 (11) |
C1 | 0.0621 (14) | 0.060 (2) | 0.0583 (15) | 0.0059 (12) | −0.0020 (12) | −0.0024 (13) |
C2 | 0.0557 (13) | 0.076 (2) | 0.0524 (14) | 0.0036 (12) | 0.0009 (10) | −0.0029 (14) |
C3 | 0.0532 (14) | 0.073 (2) | 0.0422 (14) | 0.0076 (13) | −0.0015 (11) | −0.0029 (15) |
C4 | 0.0584 (15) | 0.069 (2) | 0.0491 (15) | 0.0038 (13) | −0.0003 (11) | −0.0038 (14) |
C5 | 0.0626 (15) | 0.050 (2) | 0.0575 (16) | 0.0013 (13) | 0.0127 (13) | 0.0150 (16) |
C6 | 0.0518 (14) | 0.075 (2) | 0.0388 (14) | 0.0071 (13) | −0.0101 (12) | −0.0104 (15) |
C7 | 0.0622 (14) | 0.067 (2) | 0.0665 (17) | −0.0047 (13) | 0.0130 (11) | 0.0170 (14) |
C8 | 0.0624 (13) | 0.084 (2) | 0.0505 (13) | −0.0040 (14) | 0.0042 (10) | 0.0093 (15) |
C9 | 0.0519 (14) | 0.059 (2) | 0.0473 (14) | 0.0095 (12) | −0.0005 (11) | −0.0042 (14) |
C10 | 0.0874 (16) | 0.057 (2) | 0.0549 (15) | −0.0071 (13) | −0.0060 (13) | 0.0023 (14) |
C11 | 0.0814 (16) | 0.057 (2) | 0.0602 (17) | −0.0088 (14) | −0.0135 (13) | −0.0077 (15) |
C12 | 0.0618 (14) | 0.0515 (19) | 0.0624 (15) | −0.0036 (12) | −0.0065 (11) | 0.0001 (14) |
C13 | 0.0593 (14) | 0.063 (2) | 0.0530 (14) | −0.0006 (13) | −0.0124 (11) | −0.0010 (14) |
C14 | 0.0723 (14) | 0.069 (2) | 0.0501 (13) | 0.0106 (13) | −0.0181 (11) | 0.0045 (13) |
C15 | 0.0602 (13) | 0.0699 (19) | 0.0549 (13) | 0.0017 (12) | −0.0034 (10) | −0.0032 (14) |
C16 | 0.0713 (14) | 0.086 (2) | 0.0534 (13) | −0.0086 (13) | −0.0061 (11) | 0.0073 (14) |
C17 | 0.1056 (17) | 0.139 (3) | 0.0577 (14) | 0.0157 (17) | 0.0006 (13) | 0.0040 (15) |
Geometric parameters (Å, º) top
O1—C5 | 1.366 (2) | C9—C13 | 1.382 (2) |
O1—H1 | 0.8200 | C9—C10 | 1.398 (2) |
O2—C6 | 1.3698 (19) | C10—C11 | 1.368 (2) |
O2—H2 | 0.8200 | C10—H10 | 0.9300 |
N1—C11 | 1.327 (2) | C11—H11 | 0.9300 |
N1—C12 | 1.346 (2) | C12—C13 | 1.368 (2) |
N1—C14 | 1.4828 (19) | C12—H12 | 0.9300 |
C1—C2 | 1.321 (2) | C13—H13 | 0.9300 |
C1—C9 | 1.465 (2) | C14—C15 | 1.502 (2) |
C1—H1A | 0.9300 | C14—H14A | 0.9700 |
C2—C3 | 1.458 (2) | C14—H14B | 0.9700 |
C2—H2A | 0.9300 | C15—C16 | 1.5225 (19) |
C3—C8 | 1.387 (2) | C15—H15A | 0.9700 |
C3—C4 | 1.388 (2) | C15—H15B | 0.9700 |
C4—C5 | 1.376 (2) | C16—C17 | 1.516 (2) |
C4—H4 | 0.9300 | C16—H16A | 0.9700 |
C5—C6 | 1.392 (3) | C16—H16B | 0.9700 |
C6—C7 | 1.349 (2) | C17—H17A | 0.9600 |
C7—C8 | 1.402 (2) | C17—H17B | 0.9600 |
C7—H7 | 0.9300 | C17—H17C | 0.9600 |
C8—H8 | 0.9300 | | |
| | | |
C5—O1—H1 | 109.5 | C9—C10—H10 | 120.0 |
C6—O2—H2 | 109.5 | N1—C11—C10 | 122.1 (2) |
C11—N1—C12 | 119.39 (18) | N1—C11—H11 | 119.0 |
C11—N1—C14 | 120.26 (19) | C10—C11—H11 | 119.0 |
C12—N1—C14 | 120.3 (2) | N1—C12—C13 | 120.8 (2) |
C2—C1—C9 | 124.9 (2) | N1—C12—H12 | 119.6 |
C2—C1—H1A | 117.5 | C13—C12—H12 | 119.6 |
C9—C1—H1A | 117.5 | C12—C13—C9 | 121.2 (2) |
C1—C2—C3 | 128.6 (2) | C12—C13—H13 | 119.4 |
C1—C2—H2A | 115.7 | C9—C13—H13 | 119.4 |
C3—C2—H2A | 115.7 | N1—C14—C15 | 112.39 (15) |
C8—C3—C4 | 118.26 (19) | N1—C14—H14A | 109.1 |
C8—C3—C2 | 118.5 (2) | C15—C14—H14A | 109.1 |
C4—C3—C2 | 123.3 (2) | N1—C14—H14B | 109.1 |
C5—C4—C3 | 119.4 (2) | C15—C14—H14B | 109.1 |
C5—C4—H4 | 120.3 | H14A—C14—H14B | 107.9 |
C3—C4—H4 | 120.3 | C14—C15—C16 | 112.08 (16) |
O1—C5—C4 | 117.4 (2) | C14—C15—H15A | 109.2 |
O1—C5—C6 | 121.4 (2) | C16—C15—H15A | 109.2 |
C4—C5—C6 | 121.2 (2) | C14—C15—H15B | 109.2 |
C7—C6—O2 | 124.9 (2) | C16—C15—H15B | 109.2 |
C7—C6—C5 | 120.8 (2) | H15A—C15—H15B | 107.9 |
O2—C6—C5 | 114.3 (2) | C17—C16—C15 | 112.42 (17) |
C6—C7—C8 | 118.0 (2) | C17—C16—H16A | 109.1 |
C6—C7—H7 | 121.0 | C15—C16—H16A | 109.1 |
C8—C7—H7 | 121.0 | C17—C16—H16B | 109.1 |
C3—C8—C7 | 122.4 (2) | C15—C16—H16B | 109.1 |
C3—C8—H8 | 118.8 | H16A—C16—H16B | 107.9 |
C7—C8—H8 | 118.8 | C16—C17—H17A | 109.5 |
C13—C9—C10 | 116.46 (19) | C16—C17—H17B | 109.5 |
C13—C9—C1 | 124.2 (2) | H17A—C17—H17B | 109.5 |
C10—C9—C1 | 119.3 (2) | C16—C17—H17C | 109.5 |
C11—C10—C9 | 120.0 (2) | H17A—C17—H17C | 109.5 |
C11—C10—H10 | 120.0 | H17B—C17—H17C | 109.5 |
| | | |
C9—C1—C2—C3 | 176.94 (16) | C2—C1—C9—C13 | 0.6 (3) |
C1—C2—C3—C8 | −179.80 (19) | C2—C1—C9—C10 | −177.20 (18) |
C1—C2—C3—C4 | −1.5 (3) | C13—C9—C10—C11 | −2.2 (3) |
C8—C3—C4—C5 | 0.6 (3) | C1—C9—C10—C11 | 175.74 (17) |
C2—C3—C4—C5 | −177.70 (17) | C12—N1—C11—C10 | 1.2 (3) |
C3—C4—C5—O1 | 179.86 (18) | C14—N1—C11—C10 | −177.92 (16) |
C3—C4—C5—C6 | −0.4 (3) | C9—C10—C11—N1 | 0.8 (3) |
O1—C5—C6—C7 | 179.16 (19) | C11—N1—C12—C13 | −1.7 (3) |
C4—C5—C6—C7 | −0.6 (3) | C14—N1—C12—C13 | 177.49 (15) |
O1—C5—C6—O2 | −0.5 (3) | N1—C12—C13—C9 | 0.1 (3) |
C4—C5—C6—O2 | 179.74 (17) | C10—C9—C13—C12 | 1.8 (3) |
O2—C6—C7—C8 | −179.09 (17) | C1—C9—C13—C12 | −176.04 (15) |
C5—C6—C7—C8 | 1.3 (3) | C11—N1—C14—C15 | −73.1 (2) |
C4—C3—C8—C7 | 0.1 (3) | C12—N1—C14—C15 | 107.75 (19) |
C2—C3—C8—C7 | 178.49 (16) | N1—C14—C15—C16 | −177.77 (16) |
C6—C7—C8—C3 | −1.1 (3) | C14—C15—C16—C17 | −177.14 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 2.23 | 2.6691 (19) | 114 |
O1—H1···Cl1 | 0.82 | 2.43 | 3.1742 (15) | 151 |
O2—H2···Cl1i | 0.82 | 2.20 | 3.0027 (13) | 166 |
C11—H11···O2ii | 0.93 | 2.38 | 3.297 (2) | 170 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2. |
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