Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023713/bt2114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023713/bt2114Isup2.hkl |
CCDC reference: 613602
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 8.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.83 Sigma
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 958 Count of symmetry unique reflns 960 Completeness (_total/calc) 99.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 and local procedures.
C7H7NO4 | Dx = 1.528 Mg m−3 |
Mr = 169.14 | Melting point: 342 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1032 reflections |
a = 13.9581 (2) Å | θ = 1.0–27.5° |
b = 13.1337 (6) Å | µ = 0.13 mm−1 |
c = 4.0110 (7) Å | T = 90 K |
V = 735.30 (13) Å3 | Needle, pale yellow |
Z = 4 | 0.50 × 0.15 × 0.06 mm |
F(000) = 352 |
Nonius KappaCCD diffractometer | 958 independent reflections |
Radiation source: fine-focus sealed tube | 751 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans at fixed χ = 55° | h = −17→18 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −17→16 |
Tmin = 0.94, Tmax = 0.99 | l = −5→5 |
1613 measured reflections |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0636P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.003 |
958 reflections | Δρmax = 0.24 e Å−3 |
112 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (6) |
Experimental. The crystals were all thin, somewhat fragile needles that had a tendencu to split lengthwise. IR (taken as a thin film of a melt): 3465, 3102, 2945, 2842, 1531, 1356, 1291, 1236, 1073, 989, 828, 805, 784, 738 cm-1. |
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. This is an achiral molecule that happens to crystallize in space group P212121. Since the heaviest atom present was oxygen and the data were collected with Mo Kα radiation, the Friedel opposites were merged prior to the final round of least-squares refinement, in accordance with Acta Cryst. section E policy. The IUCr CheckCif service reports a C level alert because the value of the refined extinction parameter is 2.83 (i.e. it is less than 3). The refinement appears to be marginally better with the extinction correction included, however. Without this correction, the final R1 value is 4.14% complared to the value of R1 = 3.92 obtained with the correction. Hydrogen atoms were located in difference Fourier maps and included in the refinement using appropriate riding models. Bond parameters for H atoms were as follows: C—Har = 0.95 Å; C—HMe = 0.98 Å; O—H = 0.84 Å. Hydrogen atom displacement parameters were defined to be 1.2Ueq (C—Har) or 1.5Ueq (C—HMe; O—H) of the attached atom. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.12248 (12) | 0.35260 (12) | 0.7043 (5) | 0.0201 (5) | |
O1 | −0.03621 (12) | 0.44005 (11) | 0.4343 (6) | 0.0222 (5) | |
H1 | −0.0030 | 0.4596 | 0.5969 | 0.033* | |
O3 | 0.15196 (13) | 0.04575 (13) | 0.6390 (6) | 0.0315 (6) | |
O4 | 0.23431 (12) | 0.18489 (14) | 0.6469 (7) | 0.0338 (6) | |
N1 | 0.16092 (15) | 0.13741 (16) | 0.5860 (7) | 0.0221 (6) | |
C2 | 0.06553 (16) | 0.29504 (18) | 0.5018 (7) | 0.0166 (6) | |
C4 | 0.01458 (18) | 0.13440 (17) | 0.2551 (8) | 0.0202 (7) | |
H4 | 0.0247 | 0.0636 | 0.2217 | 0.024* | |
C6 | −0.08061 (16) | 0.28544 (19) | 0.1778 (7) | 0.0197 (6) | |
H6 | −0.1354 | 0.3179 | 0.0858 | 0.024* | |
C3 | 0.07886 (17) | 0.19133 (17) | 0.4409 (8) | 0.0178 (6) | |
C1 | −0.01693 (16) | 0.33979 (17) | 0.3694 (7) | 0.0172 (6) | |
C5 | −0.06418 (17) | 0.1821 (2) | 0.1195 (8) | 0.0222 (7) | |
H5 | −0.1076 | 0.1444 | −0.0147 | 0.027* | |
C7 | 0.19481 (17) | 0.4112 (2) | 0.5294 (8) | 0.0249 (7) | |
H7A | 0.2417 | 0.3648 | 0.4293 | 0.037* | |
H7B | 0.2273 | 0.4566 | 0.6868 | 0.037* | |
H7C | 0.1643 | 0.4517 | 0.3538 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0213 (9) | 0.0204 (9) | 0.0186 (12) | −0.0042 (7) | 0.0012 (9) | 0.0012 (9) |
O1 | 0.0256 (9) | 0.0168 (8) | 0.0242 (12) | 0.0034 (7) | −0.0040 (9) | 0.0001 (9) |
O3 | 0.0360 (10) | 0.0155 (9) | 0.0431 (15) | 0.0048 (8) | −0.0026 (12) | 0.0057 (10) |
O4 | 0.0211 (9) | 0.0286 (10) | 0.0517 (17) | 0.0010 (8) | −0.0073 (12) | 0.0061 (12) |
N1 | 0.0229 (11) | 0.0217 (12) | 0.0218 (14) | 0.0025 (9) | 0.0014 (11) | −0.0002 (11) |
C2 | 0.0182 (12) | 0.0157 (12) | 0.0159 (16) | −0.0026 (9) | 0.0017 (11) | −0.0014 (12) |
C4 | 0.0243 (13) | 0.0154 (12) | 0.0208 (18) | −0.0022 (10) | 0.0072 (13) | 0.0012 (12) |
C6 | 0.0185 (11) | 0.0220 (12) | 0.0188 (17) | 0.0012 (10) | 0.0014 (13) | 0.0055 (13) |
C3 | 0.0185 (12) | 0.0165 (12) | 0.0184 (15) | 0.0036 (10) | 0.0018 (12) | 0.0007 (13) |
C1 | 0.0211 (12) | 0.0134 (11) | 0.0170 (17) | −0.0016 (10) | 0.0048 (13) | 0.0013 (12) |
C5 | 0.0239 (13) | 0.0251 (13) | 0.0175 (16) | −0.0066 (10) | 0.0019 (13) | −0.0035 (13) |
C7 | 0.0225 (13) | 0.0215 (14) | 0.0306 (19) | −0.0050 (11) | −0.0001 (14) | 0.0008 (14) |
O2—C2 | 1.365 (3) | C4—C3 | 1.385 (4) |
O2—C7 | 1.450 (3) | C4—H4 | 0.9500 |
O1—C1 | 1.369 (3) | C6—C1 | 1.375 (4) |
O1—H1 | 0.8400 | C6—C5 | 1.396 (4) |
O3—N1 | 1.229 (3) | C6—H6 | 0.9500 |
O4—N1 | 1.224 (3) | C5—H5 | 0.9500 |
N1—C3 | 1.467 (3) | C7—H7A | 0.9800 |
C2—C3 | 1.396 (3) | C7—H7B | 0.9800 |
C2—C1 | 1.397 (3) | C7—H7C | 0.9800 |
C4—C5 | 1.377 (4) | ||
C2—O2—C7 | 114.3 (2) | C4—C3—N1 | 117.3 (2) |
C1—O1—H1 | 109.5 | C2—C3—N1 | 120.4 (2) |
O4—N1—O3 | 123.4 (2) | O1—C1—C6 | 118.6 (2) |
O4—N1—C3 | 119.1 (2) | O1—C1—C2 | 119.6 (2) |
O3—N1—C3 | 117.5 (2) | C6—C1—C2 | 121.8 (2) |
O2—C2—C3 | 124.5 (2) | C4—C5—C6 | 120.5 (3) |
O2—C2—C1 | 118.2 (2) | C4—C5—H5 | 119.8 |
C3—C2—C1 | 117.0 (2) | C6—C5—H5 | 119.8 |
C5—C4—C3 | 118.9 (2) | O2—C7—H7A | 109.5 |
C5—C4—H4 | 120.5 | O2—C7—H7B | 109.5 |
C3—C4—H4 | 120.5 | H7A—C7—H7B | 109.5 |
C1—C6—C5 | 119.5 (2) | O2—C7—H7C | 109.5 |
C1—C6—H6 | 120.3 | H7A—C7—H7C | 109.5 |
C5—C6—H6 | 120.3 | H7B—C7—H7C | 109.5 |
C4—C3—C2 | 122.3 (2) | ||
C7—O2—C2—C3 | 98.2 (3) | O4—N1—C3—C2 | −27.8 (4) |
C7—O2—C2—C1 | −88.0 (3) | O3—N1—C3—C2 | 152.4 (3) |
C5—C4—C3—C2 | 1.4 (4) | C5—C6—C1—O1 | −177.5 (3) |
C5—C4—C3—N1 | 179.0 (3) | C5—C6—C1—C2 | 1.6 (4) |
O2—C2—C3—C4 | 174.6 (3) | O2—C2—C1—O1 | 2.6 (4) |
C1—C2—C3—C4 | 0.7 (4) | C3—C2—C1—O1 | 176.9 (3) |
O2—C2—C3—N1 | −2.9 (4) | O2—C2—C1—C6 | −176.5 (2) |
C1—C2—C3—N1 | −176.7 (2) | C3—C2—C1—C6 | −2.2 (4) |
O4—N1—C3—C4 | 154.6 (3) | C3—C4—C5—C6 | −2.1 (4) |
O3—N1—C3—C4 | −25.2 (4) | C1—C6—C5—C4 | 0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.84 | 1.97 | 2.743 (2) | 153 |
O1—H1···O2 | 0.84 | 2.29 | 2.720 (2) | 112 |
Symmetry code: (i) −x, −y+1, z+1/2. |
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