Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040730/cv6616sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040730/cv6616Isup2.hkl |
CCDC reference: 296550
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.134
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.814 0.993 Tmin(prime) and Tmax expected: 0.966 0.979 RR(prime) = 0.831 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
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 2 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
To a solution of 4-aminophenol (0.545 g, 5 mmol) and triethylamine (3.0 ml) in anhydrous tetrahydrofuran (15.0 ml) and acrylic chloride in andydrous tetrahydrofuran (5.0 ml) was added dropwise with stirring. After stirring for 24 h, ice water (20 ml) was added to the reaction mixture. The resulting mixture was extracted with chroloform. The organic layer was dried over magnesium sulfate, the residue was recrystallized from ethyl acetate to give the title compound (I) (yield: 40%, 326 mg). 1H NMR (300 MHz, CDCl3): δ 5.72 (m, 1H), 6.30 (m, 2H), 6,72 (d, 2H), 7.40 (d, 2H). Crystals of (I) were obtained as blocks by recrystallization from an ethyl acetate.
All H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å, N—H = 0.86 Å, O—H = 0.82 Å and Uiso(H) = 1.2Ueq of the parent atom.
Data collection: APEXII (Bruker, 2003); cell refinement: APEXII and 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: SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL.
Fig. 1. View of (I), with 30% probability displacement ellipsoids. | |
Fig. 2. A perspective view of the crystal packing, showing the intermolecular hydrogen bonds (dashed lines). |
C9H9NO2 | Dx = 1.264 Mg m−3 |
Mr = 163.17 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2486 reflections |
a = 12.787 (4) Å | θ = 2.6–24.0° |
b = 9.918 (3) Å | µ = 0.09 mm−1 |
c = 13.524 (4) Å | T = 293 K |
V = 1715.0 (9) Å3 | Block, colourless |
Z = 8 | 0.38 × 0.30 × 0.24 mm |
F(000) = 688 |
Bruker APEX-II CCD area-detector diffractometer | 1510 independent reflections |
Radiation source: fine-focus sealed tube | 1195 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→15 |
Tmin = 0.814, Tmax = 0.993 | k = −11→11 |
8550 measured reflections | l = −16→15 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0742P)2 + 0.3734P] where P = (Fo2 + 2Fc2)/3 |
1510 reflections | (Δ/σ)max < 0.001 |
110 parameters | Δρmax = 0.30 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C9H9NO2 | V = 1715.0 (9) Å3 |
Mr = 163.17 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.787 (4) Å | µ = 0.09 mm−1 |
b = 9.918 (3) Å | T = 293 K |
c = 13.524 (4) Å | 0.38 × 0.30 × 0.24 mm |
Bruker APEX-II CCD area-detector diffractometer | 1510 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1195 reflections with I > 2σ(I) |
Tmin = 0.814, Tmax = 0.993 | Rint = 0.019 |
8550 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.30 e Å−3 |
1510 reflections | Δρmin = −0.14 e Å−3 |
110 parameters |
Experimental. Single crystal X-ray diffraction measurements were carried out with a BRUKER APEX II CCD diffractometer. The structure was solved by direct and difference Fourier methods. The final refinement was performed by full-matrix least-squares methods with anisotropic thermal parameters for non-hydrogen atoms. |
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. Full-matrix |
x | y | z | Uiso*/Ueq | ||
O1 | 0.68637 (10) | 0.35753 (15) | 0.65373 (8) | 0.0646 (4) | |
H1 | 0.6288 | 0.3913 | 0.6436 | 0.097* | |
O2 | 0.99601 (9) | 0.03185 (14) | 0.35669 (10) | 0.0643 (4) | |
N1 | 0.83017 (10) | 0.09147 (14) | 0.31687 (10) | 0.0516 (4) | |
H1B | 0.7845 | 0.0865 | 0.2703 | 0.062* | |
C1 | 0.70233 (14) | 0.22665 (19) | 0.40081 (12) | 0.0555 (5) | |
H1A | 0.6647 | 0.2288 | 0.3420 | 0.067* | |
C2 | 0.66403 (14) | 0.29334 (19) | 0.48240 (13) | 0.0565 (5) | |
H2 | 0.6011 | 0.3400 | 0.4784 | 0.068* | |
C3 | 0.71921 (13) | 0.29092 (17) | 0.57019 (12) | 0.0505 (5) | |
C4 | 0.81173 (14) | 0.2193 (2) | 0.57485 (12) | 0.0572 (5) | |
H4 | 0.8487 | 0.2163 | 0.6340 | 0.069* | |
C5 | 0.85002 (13) | 0.15245 (18) | 0.49346 (12) | 0.0541 (5) | |
H5 | 0.9123 | 0.1045 | 0.4980 | 0.065* | |
C6 | 0.79596 (13) | 0.15635 (17) | 0.40472 (11) | 0.0466 (4) | |
C7 | 0.92373 (13) | 0.03689 (17) | 0.29635 (12) | 0.0508 (5) | |
C8 | 0.93401 (17) | −0.0184 (2) | 0.19511 (15) | 0.0678 (6) | |
H8 | 0.8762 | −0.0174 | 0.1534 | 0.081* | |
C9 | 1.0226 (2) | −0.0688 (3) | 0.16251 (19) | 0.0944 (8) | |
H9A | 1.0811 | −0.0704 | 0.2034 | 0.113* | |
H9B | 1.0269 | −0.1028 | 0.0986 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0540 (8) | 0.0988 (10) | 0.0412 (7) | 0.0125 (7) | −0.0076 (6) | −0.0091 (6) |
O2 | 0.0429 (7) | 0.0926 (10) | 0.0573 (8) | 0.0061 (6) | −0.0056 (6) | 0.0037 (6) |
N1 | 0.0430 (8) | 0.0693 (9) | 0.0424 (8) | 0.0045 (7) | −0.0086 (6) | −0.0018 (7) |
C1 | 0.0482 (10) | 0.0791 (12) | 0.0393 (9) | 0.0088 (9) | −0.0124 (7) | 0.0013 (8) |
C2 | 0.0451 (10) | 0.0783 (12) | 0.0462 (10) | 0.0126 (8) | −0.0086 (8) | −0.0008 (8) |
C3 | 0.0456 (9) | 0.0669 (11) | 0.0390 (9) | 0.0011 (8) | −0.0038 (7) | 0.0016 (7) |
C4 | 0.0520 (10) | 0.0801 (12) | 0.0394 (9) | 0.0065 (9) | −0.0132 (8) | 0.0024 (8) |
C5 | 0.0440 (9) | 0.0704 (11) | 0.0478 (10) | 0.0093 (8) | −0.0103 (7) | 0.0030 (8) |
C6 | 0.0422 (9) | 0.0576 (9) | 0.0401 (9) | −0.0009 (7) | −0.0039 (7) | 0.0037 (7) |
C7 | 0.0450 (10) | 0.0585 (10) | 0.0489 (10) | −0.0010 (8) | −0.0020 (8) | 0.0050 (7) |
C8 | 0.0655 (13) | 0.0792 (13) | 0.0587 (12) | 0.0095 (10) | −0.0041 (10) | −0.0095 (10) |
C9 | 0.0901 (17) | 0.1141 (18) | 0.0790 (15) | 0.0287 (15) | 0.0020 (13) | −0.0295 (14) |
O1—C3 | 1.374 (2) | C3—C4 | 1.381 (2) |
O1—H1 | 0.8200 | C4—C5 | 1.375 (2) |
O2—C7 | 1.2339 (19) | C4—H4 | 0.9300 |
N1—C7 | 1.342 (2) | C5—C6 | 1.385 (2) |
N1—C6 | 1.420 (2) | C5—H5 | 0.9300 |
N1—H1B | 0.8600 | C7—C8 | 1.481 (3) |
C1—C2 | 1.376 (2) | C8—C9 | 1.315 (3) |
C1—C6 | 1.387 (2) | C8—H8 | 0.9300 |
C1—H1A | 0.9300 | C9—H9A | 0.9300 |
C2—C3 | 1.381 (2) | C9—H9B | 0.9300 |
C2—H2 | 0.9300 | ||
C3—O1—H1 | 109.5 | C4—C5—C6 | 120.15 (15) |
C7—N1—C6 | 129.07 (14) | C4—C5—H5 | 119.9 |
C7—N1—H1B | 115.5 | C6—C5—H5 | 119.9 |
C6—N1—H1B | 115.5 | C5—C6—C1 | 118.55 (16) |
C2—C1—C6 | 121.21 (15) | C5—C6—N1 | 123.94 (15) |
C2—C1—H1A | 119.4 | C1—C6—N1 | 117.51 (14) |
C6—C1—H1A | 119.4 | O2—C7—N1 | 123.18 (16) |
C1—C2—C3 | 119.93 (16) | O2—C7—C8 | 122.02 (16) |
C1—C2—H2 | 120.0 | N1—C7—C8 | 114.81 (15) |
C3—C2—H2 | 120.0 | C9—C8—C7 | 121.8 (2) |
O1—C3—C2 | 122.83 (15) | C9—C8—H8 | 119.1 |
O1—C3—C4 | 118.12 (14) | C7—C8—H8 | 119.1 |
C2—C3—C4 | 119.05 (16) | C8—C9—H9A | 120.0 |
C5—C4—C3 | 121.09 (15) | C8—C9—H9B | 120.0 |
C5—C4—H4 | 119.5 | H9A—C9—H9B | 120.0 |
C3—C4—H4 | 119.5 | ||
C6—C1—C2—C3 | 0.0 (3) | C2—C1—C6—C5 | 1.1 (3) |
C1—C2—C3—O1 | 178.68 (17) | C2—C1—C6—N1 | −179.43 (16) |
C1—C2—C3—C4 | −1.0 (3) | C7—N1—C6—C5 | −12.5 (3) |
O1—C3—C4—C5 | −178.79 (17) | C7—N1—C6—C1 | 168.01 (17) |
C2—C3—C4—C5 | 0.9 (3) | C6—N1—C7—O2 | 2.6 (3) |
C3—C4—C5—C6 | 0.2 (3) | C6—N1—C7—C8 | −177.74 (16) |
C4—C5—C6—C1 | −1.2 (3) | O2—C7—C8—C9 | −3.9 (3) |
C4—C5—C6—N1 | 179.38 (17) | N1—C7—C8—C9 | 176.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.86 | 2.673 (2) | 171 |
N1—H1B···O1ii | 0.86 | 2.09 | 2.916 (2) | 161 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H9NO2 |
Mr | 163.17 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 12.787 (4), 9.918 (3), 13.524 (4) |
V (Å3) | 1715.0 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.38 × 0.30 × 0.24 |
Data collection | |
Diffractometer | Bruker APEX-II CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.814, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8550, 1510, 1195 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.134, 1.06 |
No. of reflections | 1510 |
No. of parameters | 110 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.14 |
Computer programs: APEXII (Bruker, 2003), APEXII and SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg & Berndt, 1999), SHELXTL.
O1—C3 | 1.374 (2) | N1—C7 | 1.342 (2) |
O2—C7 | 1.2339 (19) | N1—C6 | 1.420 (2) |
C7—N1—C6 | 129.07 (14) | C1—C6—N1 | 117.51 (14) |
O1—C3—C2 | 122.83 (15) | O2—C7—N1 | 123.18 (16) |
O1—C3—C4 | 118.12 (14) | O2—C7—C8 | 122.02 (16) |
C5—C6—N1 | 123.94 (15) | N1—C7—C8 | 114.81 (15) |
C1—C2—C3—O1 | 178.68 (17) | C7—N1—C6—C1 | 168.01 (17) |
O1—C3—C4—C5 | −178.79 (17) | C6—N1—C7—O2 | 2.6 (3) |
C4—C5—C6—N1 | 179.38 (17) | C6—N1—C7—C8 | −177.74 (16) |
C2—C1—C6—N1 | −179.43 (16) | O2—C7—C8—C9 | −3.9 (3) |
C7—N1—C6—C5 | −12.5 (3) | N1—C7—C8—C9 | 176.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.86 | 2.673 (2) | 171 |
N1—H1B···O1ii | 0.86 | 2.09 | 2.916 (2) | 161 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, −y+1/2, z−1/2. |
The rational design of new materials in crystal engineering has been widely used for the potential applications (Desiraju, 1989; Thalladi et al., 1998; Du et al., 2005a). Recently, hydrogen bonding interactions have been widely used as the most successful strategy for engineering the structures of crystals to control molecular self-assembly in a helical structure (Gangopadhyay et al., 2001; Anthony et al., 2005; Du et al., 2005b). Furthermore, intermolecular hydrogen-bonding interactions could provide precise topological control to design novel materials. The directional nature of hydrogen bonds is exploited in the organized self-assembly of molecules in the solid state (Steed & Atwood, 2000). Here we report the synthesis and X-ray crystal structure of the title compound, (I) (Fig. 1).
The N1—C7 bond length (Table 1) is significantly shorter than a typical single C—N bond (1.47 Å; Sasada, 1984) and very close to the C═ N double-bond distance (1.28 Å; Wang et al., 1998). It is indicative of the conjugation of atoms N1, C7, O2, C8 and C9, forming a π56 configuration. The mean plane of the acrylamide moiety and the benzene ring make a dihedral angle of 11.6 (2)°. The crystal packing (Fig. 2) is characterized by the formation of two-dimensional waved sheets parallel to the ac plane via intermolecular O—H···O and N—H···O hydrogen bonds (Table 2).