In the title compound, C
11H
11ClN
2O, molecules are linked
via O—H
N hydrogen bonds, forming infinite chains running along the
c axis with a graph-set motif of
C(6). The structure is further stabilized by weak π–π and C—H
π interactions.
Supporting information
CCDC reference: 269840
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.127
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C12 ... 1.44 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. Cl .. 3.45 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C .. CG .. 2.95 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21
C11 -C10 -C12 -N2 29.00 12.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 22
C9 -C10 -C12 -N2 -154.00 12.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
2 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2-[(2-Chloro-5-ethyl-3-pyridinyl)(hydroxy)methyl]acrylonitrile
top
Crystal data top
C11H11ClN2O | Dx = 1.308 Mg m−3 |
Mr = 222.67 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pccn | Cell parameters from 9355 reflections |
a = 12.5354 (7) Å | θ = 4.6–55.8° |
b = 12.6028 (7) Å | µ = 0.31 mm−1 |
c = 14.3120 (8) Å | T = 273 K |
V = 2261.0 (2) Å3 | Needle, colourless |
Z = 8 | 0.22 × 0.18 × 0.16 mm |
F(000) = 928 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2305 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 28.0°, θmin = 2.3° |
ω scans | h = −16→16 |
18128 measured reflections | k = −16→16 |
2699 independent reflections | l = −18→18 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.072P)2 + 0.603P] where P = (Fo2 + 2Fc2)/3 |
2699 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.27 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 | |
Cl | 0.37842 (3) | 0.05310 (3) | 0.46893 (3) | 0.06364 (17) | |
C1 | 0.19522 (10) | 0.11795 (10) | 0.38405 (8) | 0.0402 (3) | |
C2 | 0.24973 (11) | 0.10375 (10) | 0.46792 (9) | 0.0431 (3) | |
C4 | 0.11175 (12) | 0.16666 (12) | 0.55488 (10) | 0.0515 (3) | |
H4 | 0.0837 | 0.1833 | 0.6132 | 0.062* | |
C5 | 0.04882 (11) | 0.18431 (11) | 0.47727 (9) | 0.0463 (3) | |
C6 | 0.09300 (11) | 0.15911 (10) | 0.39098 (8) | 0.0435 (3) | |
H6 | 0.0533 | 0.1701 | 0.3370 | 0.052* | |
C7 | −0.06325 (13) | 0.22622 (13) | 0.48628 (12) | 0.0587 (4) | |
H7A | −0.0695 | 0.2669 | 0.5436 | 0.070* | |
H7B | −0.0786 | 0.2732 | 0.4343 | 0.070* | |
C8 | −0.14268 (17) | 0.13689 (18) | 0.48731 (17) | 0.0791 (6) | |
H8A | −0.1393 | 0.0992 | 0.4291 | 0.119* | |
H8B | −0.2132 | 0.1651 | 0.4958 | 0.119* | |
H8C | −0.1263 | 0.0893 | 0.5377 | 0.119* | |
C9 | 0.24345 (11) | 0.09298 (11) | 0.28928 (9) | 0.0472 (3) | |
H9 | 0.3148 | 0.1245 | 0.2853 | 0.057* | |
C10 | 0.25159 (13) | −0.02627 (12) | 0.27315 (9) | 0.0550 (4) | |
C11 | 0.34283 (19) | −0.07841 (18) | 0.26752 (15) | 0.0824 (6) | |
H11A | 0.3429 | −0.1509 | 0.2552 | 0.099* | |
H11B | 0.4070 | −0.0427 | 0.2759 | 0.099* | |
C12 | 0.15180 (17) | −0.08047 (15) | 0.26034 (12) | 0.0670 (4) | |
N1 | 0.21063 (10) | 0.12704 (10) | 0.55109 (8) | 0.0500 (3) | |
N2 | 0.0731 (2) | −0.12483 (18) | 0.25061 (14) | 0.1002 (6) | |
O1 | 0.17735 (10) | 0.13892 (9) | 0.22102 (7) | 0.0617 (3) | |
H1 | 0.2061 | 0.1342 | 0.1697 | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0481 (2) | 0.0667 (3) | 0.0761 (3) | 0.00947 (16) | −0.01192 (16) | −0.00254 (18) |
C1 | 0.0439 (6) | 0.0407 (6) | 0.0360 (6) | −0.0027 (5) | 0.0029 (5) | −0.0004 (4) |
C2 | 0.0429 (6) | 0.0411 (6) | 0.0453 (6) | −0.0013 (5) | −0.0039 (5) | 0.0005 (5) |
C4 | 0.0604 (9) | 0.0583 (8) | 0.0358 (6) | −0.0020 (6) | 0.0047 (5) | −0.0057 (6) |
C5 | 0.0474 (7) | 0.0470 (7) | 0.0444 (7) | −0.0020 (6) | 0.0050 (5) | −0.0032 (5) |
C6 | 0.0441 (6) | 0.0499 (7) | 0.0363 (6) | −0.0004 (5) | −0.0020 (5) | 0.0006 (5) |
C7 | 0.0525 (8) | 0.0612 (9) | 0.0623 (9) | 0.0026 (7) | 0.0117 (7) | −0.0033 (7) |
C8 | 0.0606 (10) | 0.0824 (13) | 0.0942 (14) | −0.0095 (9) | 0.0049 (10) | 0.0001 (10) |
C9 | 0.0507 (7) | 0.0519 (7) | 0.0389 (6) | 0.0002 (6) | 0.0091 (5) | 0.0015 (5) |
C10 | 0.0663 (9) | 0.0565 (8) | 0.0423 (7) | 0.0036 (7) | 0.0122 (6) | −0.0060 (6) |
C11 | 0.0881 (14) | 0.0747 (12) | 0.0845 (13) | 0.0206 (11) | 0.0160 (11) | −0.0156 (10) |
C12 | 0.0862 (12) | 0.0624 (9) | 0.0525 (8) | −0.0079 (9) | 0.0093 (8) | −0.0116 (7) |
N1 | 0.0587 (7) | 0.0541 (7) | 0.0372 (5) | −0.0022 (5) | −0.0075 (5) | −0.0016 (4) |
N2 | 0.1100 (16) | 0.0986 (13) | 0.0918 (13) | −0.0363 (12) | 0.0059 (11) | −0.0203 (10) |
O1 | 0.0720 (7) | 0.0778 (7) | 0.0353 (5) | 0.0138 (6) | 0.0098 (4) | 0.0085 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.3928 (17) | C7—H7B | 0.9700 |
C1—C6 | 1.3860 (18) | C8—H8A | 0.9600 |
C1—C9 | 1.5180 (16) | C8—H8B | 0.9600 |
C2—N1 | 1.3203 (17) | C8—H8C | 0.9600 |
C2—Cl | 1.7349 (14) | C9—O1 | 1.4057 (17) |
C4—N1 | 1.337 (2) | C9—C10 | 1.524 (2) |
C4—C5 | 1.380 (2) | C9—H9 | 0.9800 |
C4—H4 | 0.9300 | C10—C11 | 1.322 (2) |
C5—C6 | 1.3902 (17) | C10—C12 | 1.437 (2) |
C5—C7 | 1.506 (2) | C11—H11A | 0.9300 |
C6—H6 | 0.9300 | C11—H11B | 0.9300 |
C7—C8 | 1.503 (3) | C12—N2 | 1.142 (3) |
C7—H7A | 0.9700 | O1—H1 | 0.8200 |
| | | |
C6—C1—C2 | 116.11 (11) | C7—C8—H8A | 109.5 |
C6—C1—C9 | 120.65 (11) | C7—C8—H8B | 109.5 |
C2—C1—C9 | 123.23 (12) | H8A—C8—H8B | 109.5 |
N1—C2—C1 | 124.49 (13) | C7—C8—H8C | 109.5 |
N1—C2—Cl | 114.81 (10) | H8A—C8—H8C | 109.5 |
C1—C2—Cl | 120.71 (10) | H8B—C8—H8C | 109.5 |
N1—C4—C5 | 123.86 (13) | O1—C9—C1 | 107.51 (11) |
N1—C4—H4 | 118.1 | O1—C9—C10 | 109.90 (12) |
C5—C4—H4 | 118.1 | C1—C9—C10 | 111.50 (11) |
C4—C5—C6 | 116.76 (13) | O1—C9—H9 | 109.3 |
C4—C5—C7 | 121.37 (12) | C1—C9—H9 | 109.3 |
C6—C5—C7 | 121.85 (13) | C10—C9—H9 | 109.3 |
C1—C6—C5 | 121.15 (12) | C11—C10—C12 | 120.62 (18) |
C1—C6—H6 | 119.4 | C11—C10—C9 | 123.89 (17) |
C5—C6—H6 | 119.4 | C12—C10—C9 | 115.45 (14) |
C8—C7—C5 | 110.86 (15) | C10—C11—H11A | 120.0 |
C8—C7—H7A | 109.5 | C10—C11—H11B | 120.0 |
C5—C7—H7A | 109.5 | H11A—C11—H11B | 120.0 |
C8—C7—H7B | 109.5 | N2—C12—C10 | 179.0 (3) |
C5—C7—H7B | 109.5 | C2—N1—C4 | 117.62 (12) |
H7A—C7—H7B | 108.1 | C9—O1—H1 | 109.5 |
| | | |
C6—C1—C2—N1 | −0.3 (2) | C2—C1—C9—O1 | −166.66 (12) |
C9—C1—C2—N1 | 178.40 (12) | C6—C1—C9—C10 | −108.58 (14) |
C6—C1—C2—Cl | −179.87 (10) | C2—C1—C9—C10 | 72.82 (16) |
C9—C1—C2—Cl | −1.21 (18) | O1—C9—C10—C11 | 128.20 (17) |
N1—C4—C5—C6 | −0.3 (2) | C1—C9—C10—C11 | −112.69 (17) |
N1—C4—C5—C7 | 178.21 (14) | O1—C9—C10—C12 | −49.42 (16) |
C2—C1—C6—C5 | 0.03 (19) | C1—C9—C10—C12 | 69.69 (16) |
C9—C1—C6—C5 | −178.67 (12) | C11—C10—C12—N2 | 29 (12) |
C4—C5—C6—C1 | 0.2 (2) | C9—C10—C12—N2 | −154 (12) |
C7—C5—C6—C1 | −178.25 (13) | C1—C2—N1—C4 | 0.2 (2) |
C4—C5—C7—C8 | −94.64 (19) | Cl—C2—N1—C4 | 179.85 (10) |
C6—C5—C7—C8 | 83.75 (19) | C5—C4—N1—C2 | 0.1 (2) |
C6—C1—C9—O1 | 11.94 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.00 | 2.8123 (15) | 174 |
C6—H6···O1 | 0.93 | 2.31 | 2.6646 (16) | 102 |
C8—H8C···Cgii | 0.96 | 2.95 | 3.581 (4) | 124 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x, −y, −z. |