Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003200/hg2170sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003200/hg2170Isup2.hkl |
CCDC reference: 636684
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: Mercury (Macrae et al., 2006) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.
C6H6NO2+·C2HO4− | F(000) = 220 |
Mr = 213.15 | Dx = 1.612 Mg m−3 Dm = 1.59 (2) Mg m−3 Dm measured by flotation using a mixture of xylene and bromoform |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 25 reflections |
a = 8.438 (6) Å | θ = 9.2–13.8° |
b = 6.048 (2) Å | µ = 0.14 mm−1 |
c = 8.774 (5) Å | T = 293 K |
β = 101.29 (3)° | Plate, colourless |
V = 439.1 (4) Å3 | 0.23 × 0.21 × 0.14 mm |
Z = 2 |
Enraf–Nonius MACH3 sealed-tube diffractometer | 865 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.0°, θmin = 2.4° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→7 |
Tmin = 0.960, Tmax = 0.978 | l = −11→10 |
1304 measured reflections | 3 standard reflections every 60 min |
1046 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0663P)2 + 0.0801P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1046 reflections | Δρmax = 0.25 e Å−3 |
101 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXTL/PC, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.029 (8) |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.69232 (17) | 0.7500 | −0.12209 (18) | 0.0302 (4) | |
C2 | 0.5436 (2) | 0.7500 | −0.0884 (2) | 0.0291 (4) | |
H2 | 0.5313 | 0.7500 | 0.0147 | 0.035* | |
C3 | 0.4096 (2) | 0.7500 | −0.20650 (19) | 0.0261 (4) | |
C31 | 0.2441 (2) | 0.7500 | −0.1678 (2) | 0.0277 (4) | |
O1A | 0.12231 (15) | 0.7500 | −0.26787 (15) | 0.0356 (4) | |
O1B | 0.24874 (15) | 0.7500 | −0.01840 (15) | 0.0391 (4) | |
C4 | 0.4309 (2) | 0.7500 | −0.3602 (2) | 0.0345 (5) | |
H4 | 0.3418 | 0.7500 | −0.4416 | 0.041* | |
C5 | 0.5860 (2) | 0.7500 | −0.3904 (2) | 0.0387 (5) | |
H5 | 0.6019 | 0.7500 | −0.4924 | 0.046* | |
C6 | 0.7164 (2) | 0.7500 | −0.2685 (2) | 0.0346 (5) | |
H6 | 0.8209 | 0.7500 | −0.2877 | 0.042* | |
H1 | 0.784 (4) | 0.7500 | −0.034 (3) | 0.054 (7)* | |
H1B | 0.135 (4) | 0.7500 | 0.008 (4) | 0.084 (10)* | |
C11 | 0.8674 (2) | 0.7500 | 0.30634 (19) | 0.0288 (4) | |
C12 | 1.0166 (2) | 0.7500 | 0.2283 (2) | 0.0297 (4) | |
O11 | 0.72923 (15) | 0.7500 | 0.23662 (15) | 0.0371 (4) | |
O12 | 0.90199 (17) | 0.7500 | 0.45935 (15) | 0.0443 (4) | |
O13 | 0.98505 (16) | 0.7500 | 0.08098 (15) | 0.0379 (4) | |
O14 | 1.14877 (16) | 0.7500 | 0.31554 (15) | 0.0451 (4) | |
H12 | 1.006 (4) | 0.7500 | 0.495 (3) | 0.056 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0160 (7) | 0.0464 (9) | 0.0280 (7) | 0.000 | 0.0034 (6) | 0.000 |
C2 | 0.0202 (8) | 0.0424 (10) | 0.0249 (8) | 0.000 | 0.0050 (7) | 0.000 |
C3 | 0.0176 (8) | 0.0361 (9) | 0.0248 (8) | 0.000 | 0.0048 (7) | 0.000 |
C31 | 0.0193 (8) | 0.0395 (10) | 0.0250 (8) | 0.000 | 0.0059 (6) | 0.000 |
O1A | 0.0173 (6) | 0.0611 (9) | 0.0276 (6) | 0.000 | 0.0021 (5) | 0.000 |
O1B | 0.0200 (6) | 0.0739 (11) | 0.0252 (7) | 0.000 | 0.0089 (5) | 0.000 |
C4 | 0.0219 (9) | 0.0553 (12) | 0.0260 (9) | 0.000 | 0.0043 (7) | 0.000 |
C5 | 0.0275 (10) | 0.0650 (13) | 0.0263 (9) | 0.000 | 0.0119 (7) | 0.000 |
C6 | 0.0208 (9) | 0.0501 (11) | 0.0359 (10) | 0.000 | 0.0128 (7) | 0.000 |
C11 | 0.0227 (8) | 0.0421 (10) | 0.0222 (8) | 0.000 | 0.0058 (6) | 0.000 |
C12 | 0.0211 (8) | 0.0438 (10) | 0.0253 (8) | 0.000 | 0.0069 (6) | 0.000 |
O11 | 0.0206 (6) | 0.0613 (9) | 0.0285 (7) | 0.000 | 0.0031 (5) | 0.000 |
O12 | 0.0233 (7) | 0.0889 (12) | 0.0214 (6) | 0.000 | 0.0060 (5) | 0.000 |
O13 | 0.0218 (6) | 0.0711 (10) | 0.0221 (6) | 0.000 | 0.0072 (5) | 0.000 |
O14 | 0.0196 (7) | 0.0846 (11) | 0.0301 (7) | 0.000 | 0.0027 (5) | 0.000 |
N1—C6 | 1.339 (2) | C4—H4 | 0.9300 |
N1—C2 | 1.344 (2) | C5—C6 | 1.376 (3) |
N1—H1 | 0.98 (3) | C5—H5 | 0.9300 |
C2—C3 | 1.376 (2) | C6—H6 | 0.9300 |
C2—H2 | 0.9300 | C11—O11 | 1.206 (2) |
C3—C4 | 1.395 (2) | C11—O12 | 1.317 (2) |
C3—C31 | 1.500 (2) | C11—C12 | 1.547 (2) |
C31—O1A | 1.214 (2) | C12—O14 | 1.223 (2) |
C31—O1B | 1.304 (2) | C12—O13 | 1.268 (2) |
O1B—H1B | 1.03 (4) | O12—H12 | 0.87 (3) |
C4—C5 | 1.385 (3) | ||
C6—N1—C2 | 122.30 (15) | C3—C4—H4 | 120.3 |
C6—N1—H1 | 120.9 (17) | C6—C5—C4 | 119.51 (17) |
C2—N1—H1 | 116.8 (17) | C6—C5—H5 | 120.2 |
N1—C2—C3 | 119.94 (16) | C4—C5—H5 | 120.2 |
N1—C2—H2 | 120.0 | N1—C6—C5 | 119.83 (16) |
C3—C2—H2 | 120.0 | N1—C6—H6 | 120.1 |
C2—C3—C4 | 119.05 (16) | C5—C6—H6 | 120.1 |
C2—C3—C31 | 119.59 (15) | O11—C11—O12 | 121.12 (17) |
C4—C3—C31 | 121.37 (15) | O11—C11—C12 | 124.43 (16) |
O1A—C31—O1B | 125.58 (17) | O12—C11—C12 | 114.46 (15) |
O1A—C31—C3 | 122.01 (16) | O14—C12—O13 | 128.46 (17) |
O1B—C31—C3 | 112.41 (14) | O14—C12—C11 | 116.40 (16) |
C31—O1B—H1B | 112.1 (18) | O13—C12—C11 | 115.14 (16) |
C5—C4—C3 | 119.37 (17) | C11—O12—H12 | 111.7 (19) |
C5—C4—H4 | 120.3 | ||
C6—N1—C2—C3 | 0.0 | C31—C3—C4—C5 | 180.0 |
N1—C2—C3—C4 | 0.0 | C3—C4—C5—C6 | 0.0 |
N1—C2—C3—C31 | 180.0 | C2—N1—C6—C5 | 0.0 |
C2—C3—C31—O1A | 180.0 | C4—C5—C6—N1 | 0.0 |
C4—C3—C31—O1A | 0.0 | O11—C11—C12—O14 | 180.0 |
C2—C3—C31—O1B | 0.0 | O12—C11—C12—O14 | 0.0 |
C4—C3—C31—O1B | 180.0 | O11—C11—C12—O13 | 0.0 |
C2—C3—C4—C5 | 0.0 | O12—C11—C12—O13 | 180.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O13 | 0.98 (3) | 1.79 (3) | 2.748 (2) | 163 (3) |
O1B—H1B···O13i | 1.03 (4) | 1.53 (4) | 2.5438 (18) | 168 (3) |
O12—H12···O1Aii | 0.87 (3) | 2.12 (3) | 2.7280 (18) | 126 (2) |
O12—H12···O14 | 0.87 (3) | 2.16 (3) | 2.6376 (19) | 114 (2) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z+1. |