Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701793X/wn2135sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701793X/wn2135IIIsup2.hkl |
CCDC reference: 647564
A commercial sample of 4-hydroxybenzamide (Sigma-Aldrich Co. Ltd, St. Louis, USA) was used. Crystals of (III) were grown by slow evaporation of an acetone solution.
The crystals were of poor quality and weakly diffracting, which accounts for the low fraction of measured reflections. The H atoms were placed in idealized locations, with C—H = 0.96 (2)–0.99 (2) Å, O—H = 0.90 (3) Å and N—H = 0.90 (3)–0.93 (3) Å, and refined as riding, with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O,C-methyl).
The molecular structure of the title compound, (III), is presented in Fig. 2. The geometric parameters of the hydrogen bonds are summarized in Table 1. The molecular packing is shown in Figs. 2 and 3.
The structure of its monohydrate was determined some years ago (Kashino et al., 1991). The unit-cell volume of (III) is 642.5 (3) Å3, whereas for the hydrate it is 746.7 (2) Å3. In (III), there are two N—H···O and one O—H···O intermolecular hydrogen bonds. In the monohydrate, there are two N—H···O, two O(water)—H···O and one O—H···O(water) intermolecular hydrogen bonds.
The crystal structures of 2-hydroxybenzamide (salicylamide), (I) (Sasada et al., 1964; Pertlik, 1990), and 3-hydroxybenzamide, (II) (Katsube et al., 1966), have also been determined previously.
For related literature, see: Kashino et al. (1991); Katsube et al. (1966); Pertlik (1990); Sasada et al. (1964); Etter (1990).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, (1996); software used to prepare material for publication: CrystalStructure.
C7H7NO2 | F(000) = 288.00 |
Mr = 137.14 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Melting point: 433.1 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71070 Å |
a = 4.5828 (15) Å | Cell parameters from 1110 reflections |
b = 8.825 (3) Å | θ = 2.6–30.1° |
c = 15.888 (5) Å | µ = 0.11 mm−1 |
β = 90.770 (7)° | T = 293 K |
V = 642.5 (3) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Rigaku Saturn CCD area-detector diffractometer | 871 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 30.6° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −6→6 |
Tmin = 0.905, Tmax = 0.979 | k = −12→12 |
5970 measured reflections | l = −22→16 |
1754 independent reflections |
Refinement on F | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.3454P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.044 | (Δ/σ)max = 0.115 |
S = 5.41 | Δρmax = 0.32 e Å−3 |
871 reflections | Δρmin = −0.15 e Å−3 |
119 parameters |
C7H7NO2 | V = 642.5 (3) Å3 |
Mr = 137.14 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.5828 (15) Å | µ = 0.11 mm−1 |
b = 8.825 (3) Å | T = 293 K |
c = 15.888 (5) Å | 0.30 × 0.20 × 0.20 mm |
β = 90.770 (7)° |
Rigaku Saturn CCD area-detector diffractometer | 1754 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 871 reflections with F2 > 2σ(F2) |
Tmin = 0.905, Tmax = 0.979 | Rint = 0.031 |
5970 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | All H-atom parameters refined |
wR(F2) = 0.044 | (Δ/σ)max = 0.115 |
S = 5.41 | Δρmax = 0.32 e Å−3 |
871 reflections | Δρmin = −0.15 e Å−3 |
119 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7483 (4) | 0.1346 (2) | 0.30494 (11) | 0.0527 (5) | |
O2 | 1.0947 (5) | 0.2443 (2) | −0.07333 (11) | 0.0543 (6) | |
N3 | 0.4860 (5) | 0.3475 (3) | 0.28422 (14) | 0.0492 (7) | |
C4 | 0.6686 (5) | 0.2409 (3) | 0.25753 (13) | 0.0398 (7) | |
C5 | 0.7782 (5) | 0.2489 (3) | 0.16993 (12) | 0.0357 (6) | |
C6 | 0.9893 (6) | 0.1458 (3) | 0.14555 (16) | 0.0431 (7) | |
C7 | 0.9875 (6) | 0.2478 (3) | 0.00638 (14) | 0.0400 (7) | |
C8 | 1.0950 (6) | 0.1447 (3) | 0.06454 (16) | 0.0461 (8) | |
C9 | 0.6756 (6) | 0.3535 (3) | 0.11146 (16) | 0.0456 (7) | |
C10 | 0.7795 (6) | 0.3522 (3) | 0.02972 (16) | 0.0460 (8) | |
H1 | 0.406 (6) | 0.334 (3) | 0.3373 (18) | 0.054 (8)* | |
H2 | 0.421 (6) | 0.422 (3) | 0.250 (2) | 0.065 (10)* | |
H3 | 0.527 (6) | 0.429 (3) | 0.1269 (18) | 0.054 (8)* | |
H4 | 0.704 (6) | 0.422 (3) | −0.0127 (19) | 0.067 (9)* | |
H5 | 0.989 (8) | 0.304 (4) | −0.108 (2) | 0.098 (15)* | |
H6 | 1.243 (7) | 0.075 (3) | 0.048 (2) | 0.074 (10)* | |
H7 | 1.054 (6) | 0.073 (3) | 0.1873 (18) | 0.057 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0770 (15) | 0.0490 (11) | 0.0321 (8) | −0.0021 (11) | 0.0042 (9) | 0.0073 (9) |
O2 | 0.0657 (14) | 0.0658 (15) | 0.0316 (9) | 0.0105 (13) | 0.0122 (9) | 0.0015 (10) |
N3 | 0.0632 (17) | 0.0505 (16) | 0.0343 (11) | 0.0026 (14) | 0.0132 (11) | 0.0018 (12) |
C4 | 0.0483 (16) | 0.0407 (15) | 0.0303 (11) | −0.0099 (15) | 0.0013 (11) | −0.0005 (12) |
C5 | 0.0420 (14) | 0.0366 (14) | 0.0285 (10) | −0.0048 (12) | 0.0025 (10) | −0.0003 (10) |
C6 | 0.0502 (16) | 0.0447 (16) | 0.0344 (12) | 0.0017 (14) | 0.0017 (11) | 0.0031 (12) |
C7 | 0.0449 (14) | 0.0446 (16) | 0.0305 (10) | −0.0048 (14) | 0.0056 (10) | −0.0039 (12) |
C8 | 0.0506 (17) | 0.0485 (17) | 0.0392 (13) | 0.0070 (15) | 0.0058 (12) | −0.0009 (13) |
C9 | 0.0532 (17) | 0.0488 (17) | 0.0352 (12) | 0.0103 (16) | 0.0105 (11) | 0.0039 (13) |
C10 | 0.0555 (18) | 0.0517 (18) | 0.0310 (12) | 0.0065 (16) | 0.0071 (11) | 0.0088 (13) |
O1—C4 | 1.254 (3) | C9—C10 | 1.389 (3) |
O2—C7 | 1.365 (3) | O2—H5 | 0.90 (3) |
N3—C4 | 1.333 (3) | N3—H1 | 0.93 (3) |
C4—C5 | 1.488 (3) | N3—H2 | 0.90 (3) |
C5—C6 | 1.387 (4) | C6—H7 | 0.96 (2) |
C5—C9 | 1.387 (3) | C8—H6 | 0.96 (3) |
C6—C8 | 1.381 (3) | C9—H3 | 0.99 (2) |
C7—C8 | 1.383 (4) | C10—H4 | 0.97 (3) |
C7—C10 | 1.380 (4) | ||
O1—C4—N3 | 121.1 (2) | C7—O2—H5 | 111 (2) |
O1—C4—C5 | 119.9 (2) | C4—N3—H1 | 116.8 (18) |
N3—C4—C5 | 119.0 (2) | C4—N3—H2 | 122 (2) |
C4—C5—C6 | 118.4 (2) | H1—N3—H2 | 121 (2) |
C4—C5—C9 | 122.9 (2) | C5—C6—H7 | 116.9 (17) |
C6—C5—C9 | 118.7 (2) | C8—C6—H7 | 121.8 (17) |
C5—C6—C8 | 121.3 (2) | C6—C8—H6 | 121.2 (19) |
O2—C7—C8 | 118.4 (2) | C7—C8—H6 | 119.4 (19) |
O2—C7—C10 | 121.5 (2) | C5—C9—H3 | 120.8 (16) |
C8—C7—C10 | 120.1 (2) | C10—C9—H3 | 119.0 (16) |
C6—C8—C7 | 119.4 (2) | C7—C10—H4 | 118.6 (18) |
C5—C9—C10 | 120.2 (2) | C9—C10—H4 | 121.2 (18) |
C7—C10—C9 | 120.2 (2) | ||
O1—C4—C5—C6 | −6.2 (4) | C9—C5—C6—C8 | −0.8 (4) |
O1—C4—C5—C9 | 172.9 (2) | C5—C6—C8—C7 | −0.3 (4) |
N3—C4—C5—C6 | 173.9 (2) | O2—C7—C8—C6 | −179.8 (2) |
N3—C4—C5—C9 | −7.0 (4) | O2—C7—C10—C9 | −179.7 (2) |
C4—C5—C6—C8 | 178.4 (2) | C8—C7—C10—C9 | −0.5 (4) |
C4—C5—C9—C10 | −177.9 (2) | C10—C7—C8—C6 | 0.9 (4) |
C6—C5—C9—C10 | 1.2 (4) | C5—C9—C10—C7 | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H5···O1i | 0.90 (3) | 1.84 (3) | 2.706 (2) | 161 (2) |
N3—H1···O2ii | 0.93 (3) | 2.14 (3) | 3.017 (3) | 156 (2) |
N3—H2···O1iii | 0.90 (3) | 2.21 (3) | 3.088 (3) | 166 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C7H7NO2 |
Mr | 137.14 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 4.5828 (15), 8.825 (3), 15.888 (5) |
β (°) | 90.770 (7) |
V (Å3) | 642.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Rigaku Saturn CCD area-detector |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.905, 0.979 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 5970, 1754, 871 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.716 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.044, 5.41 |
No. of reflections | 871 |
No. of parameters | 119 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
(Δ/σ)max | 0.115 |
Δρmax, Δρmin (e Å−3) | 0.32, −0.15 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, CrystalStructure (Rigaku/MSC, 2005), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, (1996), CrystalStructure.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H5···O1i | 0.90 (3) | 1.84 (3) | 2.706 (2) | 161 (2) |
N3—H1···O2ii | 0.93 (3) | 2.14 (3) | 3.017 (3) | 156 (2) |
N3—H2···O1iii | 0.90 (3) | 2.21 (3) | 3.088 (3) | 166 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
The molecular structure of the title compound, (III), is presented in Fig. 2. The geometric parameters of the hydrogen bonds are summarized in Table 1. The molecular packing is shown in Figs. 2 and 3.
The structure of its monohydrate was determined some years ago (Kashino et al., 1991). The unit-cell volume of (III) is 642.5 (3) Å3, whereas for the hydrate it is 746.7 (2) Å3. In (III), there are two N—H···O and one O—H···O intermolecular hydrogen bonds. In the monohydrate, there are two N—H···O, two O(water)—H···O and one O—H···O(water) intermolecular hydrogen bonds.
The crystal structures of 2-hydroxybenzamide (salicylamide), (I) (Sasada et al., 1964; Pertlik, 1990), and 3-hydroxybenzamide, (II) (Katsube et al., 1966), have also been determined previously.