Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compounds (both C9H10O4) have nearly planar structures, and the methyl and/or carboxylic acid groups lie out of the molecular plane, as dictated by steric interactions. 2,5-Di­methoxy­benzoic acid (2,5-DMBA) forms an unusual intramolecular hydrogen bond between the carboxylic acid group and the O atom of the methoxy group in the 2-position [O...O = 2.547 (2) Å and O—H...O = 154 (3)°]. 2,4-DMBA forms a typical hydrogen-bond dimer with a neighboring mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104003063/fr1460sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104003063/fr1460Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104003063/fr1460IIsup3.hkl
Contains datablock II

CCDC references: 237939; 237940

Comment top

The crystal structures of only four of the six isomers of dimethoxybenzoic acid (DMBA) have been determined previously. These four isomers exhibit considerable conformational differences. For example, the plane defined by the carboxylic acid group lies nearly parallel to the aromatic ring plane in 3,4-DMBA (3.4°; Pinkus et al., 2002) and 3,5-DMBA (1.4°; Lynch et al., 1994), but is 36.5 and 56.2° out of the plane in 2,3-DMBA (Swaminathan et al., 1977; Bryan & White, 1982a) and 2,6-DMBA (Swaminathan et al., 1976; Bryan & White, 1982b). For the title compounds, this angle is 6.3 (2) (2,4-DMBA) and 2.3 (3)° (2,5-DMBA).

The 2,4-dimethoxybenzoic acid (DMBA) isomer (Fig. 1) exhibits the relatively common intermolecular hydrogen-bond arrangment between the carboxylic acid of two molecules centered about an inversion center. This overall hydrogen-bonding arrangement is also found in 2,3-DMBA (Swaminathan et al., 1977; Bryan & White, 1982a), 3,4-DMBA (Pinkus et al., 2002) and 3,5-DMBA (Lynch et al., 1994), as welll as in 2-methoxybenzoic acid (Parvez, 1987) and 4-methoxybenzoic acid (Etter et al., 1988), the two monomethoxybenzoic acids with determined crystal structures.

The hydrogen-bonding arrangement of 2,5-DMBA (Fig. 2) is unusual in that, unlike most of the DMBA isomers, the carboxylic acid group does not hydrogen bond with a neighboring molecule's carboxylic acid group but instead forms an intramolecular hydrogen bond with the methoxy O atom that is bonded to atom C2. The donor–acceptor distance of this intramolecular hydrogen bond is 2.547 (2) Å and the angle from the donor to the H atom to the acceptor is 154 (3)°.

Experimental top

2,4-Dimethoxybenzoic acid (C9H10O4) and 2,5-dimethoxybenzoic acid (C9H10O4) were obtained from Aldrich and used without purification. Each sample was recrystallized from methanol.

Refinement top

The positions of the H atoms on the carboxylic groups were found from difference maps and refined independently. The positions of all other H atoms were determined geometrically and refined with a riding model. The displacement parameters for the H atoms were assigned values of 1.2Uiso (1.5Uiso for methyl groups) of the carrier atom. Bonds between H atoms and aromatic C atoms were set to 0.95 Å; bonds between H atoms and methyl C atoms were set to 0.98 Å.

Computing details top

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A molecular structure diagram of 2,4-DMBA. 50% probability displacement ellipsoids and the atom-numbering scheme are shown.
[Figure 2] Fig. 2. A molecular structure diagram of 2,5-DMBA, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Also shown is the intramolecular hydrogen bond (see text).
(I) 2,4-dimethoxybenzoic acid top
Crystal data top
C9H10O4Z = 2
Mr = 182.17F(000) = 192
Triclinic, P1Dx = 1.472 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7602 (13) ÅCell parameters from 1306 reflections
b = 7.7124 (15) Åθ = 2.6–26.0°
c = 8.0237 (15) ŵ = 0.12 mm1
α = 94.995 (4)°T = 100 K
β = 95.894 (4)°Block, colorless
γ = 96.759 (4)°0.22 × 0.17 × 0.04 mm
V = 411.14 (14) Å3
Data collection top
Bruker SMART APEX
diffractometer
1563 independent reflections
Radiation source: fine-focus sealed tube1298 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
ω scanθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 78
Tmin = 0.975, Tmax = 0.995k = 99
2584 measured reflectionsl = 97
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
1563 reflections(Δ/σ)max = 0.001
121 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C9H10O4γ = 96.759 (4)°
Mr = 182.17V = 411.14 (14) Å3
Triclinic, P1Z = 2
a = 6.7602 (13) ÅMo Kα radiation
b = 7.7124 (15) ŵ = 0.12 mm1
c = 8.0237 (15) ÅT = 100 K
α = 94.995 (4)°0.22 × 0.17 × 0.04 mm
β = 95.894 (4)°
Data collection top
Bruker SMART APEX
diffractometer
1563 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
1298 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.995Rint = 0.012
2584 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.37 e Å3
1563 reflectionsΔρmin = 0.43 e Å3
121 parameters
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
xyzUiso*/Ueq
O10.32568 (15)0.66932 (14)0.49547 (14)0.0201 (3)
O20.31184 (16)0.44318 (14)0.65036 (15)0.0220 (3)
H20.440 (3)0.413 (2)0.599 (3)0.026*
O30.03560 (16)0.40777 (14)0.81414 (15)0.0197 (3)
O40.56153 (16)0.87315 (14)0.83949 (15)0.0207 (3)
C10.0226 (2)0.65497 (19)0.66673 (19)0.0167 (4)
C20.1060 (2)0.5678 (2)0.7711 (2)0.0163 (4)
C30.3004 (2)0.6476 (2)0.8251 (2)0.0174 (4)
H30.38750.58950.89530.021*
C40.3688 (2)0.8112 (2)0.7776 (2)0.0181 (4)
C50.2451 (2)0.8997 (2)0.6758 (2)0.0190 (4)
H50.29081.01210.64420.023*
C60.0522 (2)0.8185 (2)0.6218 (2)0.0184 (4)
H60.03320.87720.55070.022*
C70.2321 (2)0.58778 (19)0.5979 (2)0.0159 (4)
C80.1728 (2)0.3211 (2)0.9146 (2)0.0216 (4)
H8A0.10610.20690.93660.032*
H8B0.21710.39311.02170.032*
H8C0.28910.30390.85450.032*
C90.6450 (2)1.0374 (2)0.7891 (2)0.0232 (4)
H9A0.78591.06390.83670.035*
H9B0.57011.13060.83030.035*
H9C0.63601.03010.66600.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0118 (6)0.0220 (6)0.0238 (7)0.0025 (4)0.0067 (5)0.0046 (5)
O20.0113 (6)0.0226 (6)0.0289 (7)0.0062 (4)0.0072 (5)0.0078 (5)
O30.0127 (6)0.0180 (5)0.0262 (7)0.0032 (4)0.0067 (5)0.0073 (5)
O40.0098 (6)0.0218 (6)0.0269 (7)0.0061 (4)0.0072 (5)0.0036 (5)
C10.0103 (8)0.0202 (8)0.0174 (9)0.0018 (6)0.0031 (6)0.0004 (6)
C20.0124 (7)0.0173 (8)0.0174 (9)0.0026 (6)0.0010 (6)0.0013 (6)
C30.0112 (8)0.0205 (8)0.0188 (9)0.0002 (6)0.0054 (6)0.0029 (6)
C40.0106 (8)0.0221 (8)0.0189 (9)0.0028 (6)0.0026 (6)0.0022 (6)
C50.0138 (8)0.0174 (7)0.0235 (9)0.0042 (6)0.0038 (6)0.0045 (6)
C60.0134 (8)0.0200 (8)0.0202 (9)0.0006 (6)0.0045 (6)0.0037 (6)
C70.0117 (8)0.0178 (7)0.0166 (8)0.0002 (6)0.0030 (6)0.0003 (6)
C80.0151 (8)0.0209 (8)0.0272 (9)0.0013 (6)0.0055 (7)0.0073 (6)
C90.0128 (8)0.0235 (8)0.0298 (10)0.0073 (6)0.0037 (7)0.0033 (7)
Geometric parameters (Å, º) top
O1—C71.2441 (18)C3—H30.9500
O2—C71.3031 (19)C4—C51.387 (2)
O2—H20.91 (2)C5—C61.387 (2)
O3—C21.3560 (18)C5—H50.9500
O3—C81.429 (2)C6—H60.9500
O4—C41.3607 (18)C8—H8A0.9800
O4—C91.4332 (19)C8—H8B0.9800
C1—C61.394 (2)C8—H8C0.9800
C1—C21.412 (2)C9—H9A0.9800
C1—C71.482 (2)C9—H9B0.9800
C2—C31.393 (2)C9—H9C0.9800
C3—C41.390 (2)
C7—O2—H2109.7 (12)C5—C6—C1123.24 (14)
C2—O3—C8116.76 (12)C5—C6—H6118.4
C4—O4—C9117.53 (12)C1—C6—H6118.4
C6—C1—C2117.98 (14)O1—C7—O2122.48 (13)
C6—C1—C7116.10 (14)O1—C7—C1120.21 (14)
C2—C1—C7125.91 (14)O2—C7—C1117.31 (13)
O3—C2—C3122.24 (14)O3—C8—H8A109.5
O3—C2—C1118.51 (13)O3—C8—H8B109.5
C3—C2—C1119.25 (13)H8A—C8—H8B109.5
C4—C3—C2120.89 (14)O3—C8—H8C109.5
C4—C3—H3119.6H8A—C8—H8C109.5
C2—C3—H3119.6H8B—C8—H8C109.5
O4—C4—C5124.54 (14)O4—C9—H9A109.5
O4—C4—C3114.54 (13)O4—C9—H9B109.5
C5—C4—C3120.92 (14)H9A—C9—H9B109.5
C4—C5—C6117.71 (14)O4—C9—H9C109.5
C4—C5—H5121.1H9A—C9—H9C109.5
C6—C5—H5121.1H9B—C9—H9C109.5
C8—O3—C2—C31.7 (2)C2—C3—C4—C50.3 (3)
C8—O3—C2—C1177.73 (14)O4—C4—C5—C6179.60 (15)
C6—C1—C2—O3179.31 (14)C3—C4—C5—C60.7 (2)
C7—C1—C2—O30.1 (3)C4—C5—C6—C10.9 (3)
C6—C1—C2—C30.2 (2)C2—C1—C6—C50.6 (3)
C7—C1—C2—C3179.57 (14)C7—C1—C6—C5179.91 (15)
O3—C2—C3—C4179.45 (14)C6—C1—C7—O15.6 (2)
C1—C2—C3—C40.0 (2)C2—C1—C7—O1173.80 (14)
C9—O4—C4—C53.2 (2)C6—C1—C7—O2173.78 (13)
C9—O4—C4—C3177.13 (13)C2—C1—C7—O26.8 (2)
C2—C3—C4—O4179.99 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.91 (2)1.71 (2)2.6192 (15)172.7 (18)
Symmetry code: (i) x1, y+1, z+1.
(II) 2,5-dimethoxybenzoic acid top
Crystal data top
C9H10O4F(000) = 384
Mr = 182.17Dx = 1.444 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2576 reflections
a = 10.0810 (17) Åθ = 2.6–26.0°
b = 12.534 (2) ŵ = 0.11 mm1
c = 6.6408 (11) ÅT = 100 K
β = 92.729 (4)°Block, colorless
V = 838.1 (2) Å30.33 × 0.17 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
1633 independent reflections
Radiation source: fine-focus sealed tube1421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scanθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1211
Tmin = 0.963, Tmax = 0.993k = 1515
5021 measured reflectionsl = 88
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.086P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
1633 reflections(Δ/σ)max = 0.007
122 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C9H10O4V = 838.1 (2) Å3
Mr = 182.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0810 (17) ŵ = 0.11 mm1
b = 12.534 (2) ÅT = 100 K
c = 6.6408 (11) Å0.33 × 0.17 × 0.06 mm
β = 92.729 (4)°
Data collection top
Bruker SMART APEX
diffractometer
1633 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
1421 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.993Rint = 0.023
5021 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.51 e Å3
1633 reflectionsΔρmin = 0.34 e Å3
122 parameters
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
xyzUiso*/Ueq
O10.71941 (17)0.05660 (13)0.2269 (3)0.0212 (4)
O20.57149 (18)0.18440 (15)0.1831 (3)0.0277 (5)
H20.574 (3)0.255 (3)0.176 (5)0.033*
O30.64950 (17)0.37763 (13)0.1990 (3)0.0209 (5)
O41.16150 (16)0.22282 (13)0.3016 (3)0.0209 (5)
C10.8032 (2)0.23472 (18)0.2342 (3)0.0154 (5)
C20.7797 (2)0.34550 (19)0.2273 (3)0.0164 (5)
C30.8850 (3)0.41606 (18)0.2465 (4)0.0188 (5)
H30.86880.49070.24260.023*
C41.0148 (2)0.37824 (19)0.2714 (4)0.0180 (5)
H41.08690.42690.28370.022*
C51.0382 (2)0.26884 (19)0.2780 (3)0.0165 (5)
C60.9329 (2)0.19846 (18)0.2591 (3)0.0162 (5)
H60.94960.12390.26320.019*
C70.6968 (2)0.15122 (19)0.2155 (3)0.0177 (5)
C80.6182 (3)0.48894 (19)0.2224 (4)0.0228 (6)
H8A0.52170.49850.21290.034*
H8B0.65850.53020.11590.034*
H8C0.65330.51380.35440.034*
C91.2719 (2)0.2943 (2)0.3229 (4)0.0236 (6)
H9A1.27430.33980.20310.035*
H9B1.35440.25310.33760.035*
H9C1.26250.33890.44250.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0196 (9)0.0117 (9)0.0324 (10)0.0018 (7)0.0034 (7)0.0007 (7)
O20.0160 (9)0.0129 (9)0.0540 (13)0.0013 (7)0.0001 (8)0.0020 (8)
O30.0161 (9)0.0106 (8)0.0359 (10)0.0018 (6)0.0002 (7)0.0015 (7)
O40.0138 (9)0.0131 (9)0.0359 (10)0.0004 (7)0.0015 (7)0.0006 (7)
C10.0187 (12)0.0121 (11)0.0158 (11)0.0022 (9)0.0025 (9)0.0009 (8)
C20.0165 (12)0.0155 (12)0.0171 (11)0.0026 (9)0.0015 (9)0.0006 (8)
C30.0239 (13)0.0085 (10)0.0241 (12)0.0001 (9)0.0022 (10)0.0002 (9)
C40.0173 (12)0.0127 (11)0.0238 (12)0.0040 (9)0.0009 (9)0.0010 (9)
C50.0170 (12)0.0148 (12)0.0178 (12)0.0008 (9)0.0024 (9)0.0003 (8)
C60.0206 (12)0.0105 (11)0.0177 (11)0.0004 (9)0.0037 (9)0.0009 (8)
C70.0182 (12)0.0155 (12)0.0195 (12)0.0006 (9)0.0026 (9)0.0009 (9)
C80.0227 (13)0.0123 (12)0.0331 (14)0.0063 (10)0.0014 (10)0.0019 (10)
C90.0159 (12)0.0205 (13)0.0346 (15)0.0025 (10)0.0020 (10)0.0008 (10)
Geometric parameters (Å, º) top
O1—C71.209 (3)C3—H30.9500
O2—C71.338 (3)C4—C51.392 (3)
O2—H20.88 (4)C4—H40.9500
O3—C21.377 (3)C5—C61.381 (3)
O3—C81.440 (3)C6—H60.9500
O4—C51.372 (3)C8—H8A0.9800
O4—C91.430 (3)C8—H8B0.9800
C1—C61.386 (3)C8—H8C0.9800
C1—C21.409 (3)C9—H9A0.9800
C1—C71.499 (3)C9—H9B0.9800
C2—C31.383 (3)C9—H9C0.9800
C3—C41.394 (4)
C7—O2—H2107 (2)C5—C6—C1121.2 (2)
C2—O3—C8118.72 (19)C5—C6—H6119.4
C5—O4—C9116.37 (18)C1—C6—H6119.4
C6—C1—C2118.9 (2)O1—C7—O2119.2 (2)
C6—C1—C7116.6 (2)O1—C7—C1123.2 (2)
C2—C1—C7124.5 (2)O2—C7—C1117.6 (2)
O3—C2—C3123.2 (2)O3—C8—H8A109.5
O3—C2—C1116.8 (2)O3—C8—H8B109.5
C3—C2—C1120.0 (2)H8A—C8—H8B109.5
C2—C3—C4120.4 (2)O3—C8—H8C109.5
C2—C3—H3119.8H8A—C8—H8C109.5
C4—C3—H3119.8H8B—C8—H8C109.5
C5—C4—C3119.7 (2)O4—C9—H9A109.5
C5—C4—H4120.1O4—C9—H9B109.5
C3—C4—H4120.1H9A—C9—H9B109.5
O4—C5—C6115.5 (2)O4—C9—H9C109.5
O4—C5—C4124.7 (2)H9A—C9—H9C109.5
C6—C5—C4119.9 (2)H9B—C9—H9C109.5
C8—O3—C2—C310.3 (3)C3—C4—C5—O4179.9 (2)
C8—O3—C2—C1170.4 (2)C3—C4—C5—C60.3 (4)
C6—C1—C2—O3178.9 (2)O4—C5—C6—C1179.9 (2)
C7—C1—C2—O30.8 (3)C4—C5—C6—C10.3 (3)
C6—C1—C2—C30.4 (3)C2—C1—C6—C50.3 (3)
C7—C1—C2—C3179.9 (2)C7—C1—C6—C5179.9 (2)
O3—C2—C3—C4178.9 (2)C6—C1—C7—O12.2 (3)
C1—C2—C3—C40.4 (4)C2—C1—C7—O1178.1 (2)
C2—C3—C4—C50.3 (4)C6—C1—C7—O2177.3 (2)
C9—O4—C5—C6179.6 (2)C2—C1—C7—O22.4 (3)
C9—O4—C5—C40.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.88 (4)1.72 (4)2.547 (2)154 (3)

Experimental details

(I)(II)
Crystal data
Chemical formulaC9H10O4C9H10O4
Mr182.17182.17
Crystal system, space groupTriclinic, P1Monoclinic, P21/c
Temperature (K)100100
a, b, c (Å)6.7602 (13), 7.7124 (15), 8.0237 (15)10.0810 (17), 12.534 (2), 6.6408 (11)
α, β, γ (°)94.995 (4), 95.894 (4), 96.759 (4)90, 92.729 (4), 90
V3)411.14 (14)838.1 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.120.11
Crystal size (mm)0.22 × 0.17 × 0.040.33 × 0.17 × 0.06
Data collection
DiffractometerBruker SMART APEX
diffractometer
Bruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Multi-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.975, 0.9950.963, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
2584, 1563, 1298 5021, 1633, 1421
Rint0.0120.023
(sin θ/λ)max1)0.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.136, 1.04 0.060, 0.168, 1.01
No. of reflections15631633
No. of parameters121122
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.430.51, 0.34

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.91 (2)1.71 (2)2.6192 (15)172.7 (18)
Symmetry code: (i) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.88 (4)1.72 (4)2.547 (2)154 (3)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds