Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700743X/bt2270sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700743X/bt2270VIsup2.hkl |
CCDC reference: 640281
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.120
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.77 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 70.06 From the CIF: _reflns_number_total 754 Count of symmetry unique reflns 754 Completeness (_total/calc) 100.00% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5B = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C7H8O3 | Dx = 1.416 Mg m−3 |
Mr = 140.14 | Melting point: 75.3 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 4.8759 (5) Å | θ = 26–36° |
b = 9.5110 (8) Å | µ = 0.94 mm−1 |
c = 14.1724 (11) Å | T = 298 K |
V = 657.24 (10) Å3 | Needle, colourless |
Z = 4 | 0.60 × 0.12 × 0.06 mm |
F(000) = 296 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.043 |
Radiation source: rotating anode | θmax = 70.1°, θmin = 5.6° |
Graphite monochromator | h = −5→5 |
ω/2θ scans | k = −11→11 |
1508 measured reflections | l = −17→17 |
754 independent reflections | 3 standard reflections every 60 min |
593 reflections with I > 2σ(I) | intensity decay: 10% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | Only H-atom displacement parameters refined |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0652P)2 + 0.0616P] where P = (Fo2 + 2Fc2)/3 |
754 reflections | (Δ/σ)max < 0.001 |
97 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | ||
O1 | 0.3693 (4) | −0.0810 (3) | 0.55389 (16) | 0.0664 (7) | |
C1A | 0.1292 (7) | −0.0761 (4) | 0.4944 (2) | 0.0681 (9) | |
H1A | 0.1201 | −0.1337 | 0.4371 | 0.077 (11)* | |
C2 | −0.0097 (8) | 0.0628 (4) | 0.4977 (3) | 0.0759 (10) | |
H21 | −0.1815 | 0.0600 | 0.4632 | 0.091 (9)* | |
H22 | 0.1061 | 0.1352 | 0.4705 | 0.091 (9)* | |
C2A | −0.0597 (7) | 0.0907 (4) | 0.6012 (2) | 0.0643 (9) | |
H2A | −0.2414 | 0.1322 | 0.6111 | 0.074 (11)* | |
O3 | 0.1541 (6) | 0.1796 (2) | 0.64129 (18) | 0.0733 (7) | |
C4 | 0.2665 (8) | 0.1218 (4) | 0.7182 (3) | 0.0649 (9) | |
C5 | 0.1274 (7) | −0.0133 (4) | 0.7415 (2) | 0.0632 (9) | |
H51 | 0.0060 | −0.0020 | 0.7952 | 0.108 (11)* | |
H52 | 0.2608 | −0.0859 | 0.7559 | 0.108 (11)* | |
C5A | −0.0333 (6) | −0.0502 (3) | 0.65367 (19) | 0.0521 (7) | |
H5A | −0.2136 | −0.0893 | 0.6694 | 0.078 (11)* | |
C5B | 0.1166 (7) | −0.1416 (3) | 0.5859 (2) | 0.0604 (9) | |
H5B | 0.0993 | −0.2440 | 0.5906 | 0.083 (11)* | |
O6 | 0.4511 (7) | 0.1785 (3) | 0.7596 (2) | 0.0966 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0437 (11) | 0.0740 (15) | 0.0814 (15) | 0.0033 (12) | −0.0006 (12) | −0.0160 (13) |
C1A | 0.0580 (18) | 0.085 (2) | 0.0615 (19) | −0.007 (2) | −0.0077 (18) | −0.0113 (19) |
C2 | 0.067 (2) | 0.088 (2) | 0.073 (2) | 0.000 (2) | −0.007 (2) | 0.025 (2) |
C2A | 0.0460 (16) | 0.0570 (17) | 0.090 (2) | 0.0086 (16) | 0.0085 (17) | 0.0097 (17) |
O3 | 0.0845 (16) | 0.0443 (10) | 0.0913 (17) | −0.0052 (13) | 0.0232 (17) | 0.0011 (12) |
C4 | 0.066 (2) | 0.0584 (18) | 0.071 (2) | −0.0114 (18) | 0.0243 (19) | −0.0215 (17) |
C5 | 0.063 (2) | 0.068 (2) | 0.0579 (17) | −0.0123 (18) | 0.0102 (19) | −0.0003 (15) |
C5A | 0.0420 (15) | 0.0505 (16) | 0.0639 (18) | −0.0065 (14) | 0.0015 (15) | 0.0069 (14) |
C5B | 0.057 (2) | 0.0475 (16) | 0.077 (2) | −0.0065 (15) | −0.0075 (18) | −0.0068 (15) |
O6 | 0.092 (2) | 0.103 (2) | 0.0948 (19) | −0.0387 (19) | 0.0165 (17) | −0.0450 (15) |
O1—C5B | 1.434 (4) | C2A—H2A | 0.9800 |
O1—C1A | 1.444 (4) | O3—C4 | 1.338 (4) |
C1A—C5B | 1.440 (5) | C4—O6 | 1.202 (4) |
C1A—C2 | 1.485 (5) | C4—C5 | 1.490 (5) |
C1A—H1A | 0.9800 | C5—C5A | 1.513 (4) |
C2—C2A | 1.511 (5) | C5—H51 | 0.9700 |
C2—H21 | 0.9700 | C5—H52 | 0.9700 |
C2—H22 | 0.9700 | C5A—C5B | 1.487 (4) |
C2A—O3 | 1.458 (4) | C5A—H5A | 0.9800 |
C2A—C5A | 1.538 (4) | C5B—H5B | 0.9800 |
C5B—O1—C1A | 60.1 (2) | O6—C4—C5 | 128.2 (4) |
C5B—C1A—O1 | 59.6 (2) | O3—C4—C5 | 110.4 (3) |
C5B—C1A—C2 | 109.7 (3) | C4—C5—C5A | 104.6 (3) |
O1—C1A—C2 | 112.3 (3) | C4—C5—H51 | 110.8 |
C5B—C1A—H1A | 120.2 | C5A—C5—H51 | 110.8 |
O1—C1A—H1A | 120.2 | C4—C5—H52 | 110.8 |
C2—C1A—H1A | 120.2 | C5A—C5—H52 | 110.8 |
C1A—C2—C2A | 105.1 (3) | H51—C5—H52 | 108.9 |
C1A—C2—H21 | 110.7 | C5B—C5A—C5 | 114.4 (3) |
C2A—C2—H21 | 110.7 | C5B—C5A—C2A | 103.7 (3) |
C1A—C2—H22 | 110.7 | C5—C5A—C2A | 103.9 (2) |
C2A—C2—H22 | 110.7 | C5B—C5A—H5A | 111.5 |
H21—C2—H22 | 108.8 | C5—C5A—H5A | 111.5 |
O3—C2A—C2 | 111.4 (3) | C2A—C5A—H5A | 111.5 |
O3—C2A—C5A | 104.9 (3) | O1—C5B—C1A | 60.3 (2) |
C2—C2A—C5A | 107.6 (3) | O1—C5B—C5A | 113.1 (2) |
O3—C2A—H2A | 110.9 | C1A—C5B—C5A | 110.5 (3) |
C2—C2A—H2A | 110.9 | O1—C5B—H5B | 119.6 |
C5A—C2A—H2A | 110.9 | C1A—C5B—H5B | 119.6 |
C4—O3—C2A | 111.9 (3) | C5A—C5B—H5B | 119.6 |
O6—C4—O3 | 121.3 (4) | ||
C5B—O1—C1A—C2 | 100.4 (3) | O3—C2A—C5A—C5B | −100.9 (3) |
C5B—C1A—C2—C2A | 10.7 (4) | C2—C2A—C5A—C5B | 17.8 (4) |
O1—C1A—C2—C2A | −53.6 (4) | O3—C2A—C5A—C5 | 18.9 (3) |
C1A—C2—C2A—O3 | 96.8 (3) | C2—C2A—C5A—C5 | 137.7 (3) |
C1A—C2—C2A—C5A | −17.6 (4) | C1A—O1—C5B—C5A | −101.3 (3) |
C2—C2A—O3—C4 | −126.7 (3) | C2—C1A—C5B—O1 | −104.9 (3) |
C5A—C2A—O3—C4 | −10.6 (3) | O1—C1A—C5B—C5A | 105.6 (3) |
C2A—O3—C4—O6 | 178.2 (3) | C2—C1A—C5B—C5A | 0.6 (4) |
C2A—O3—C4—C5 | −2.7 (4) | C5—C5A—C5B—O1 | −58.4 (3) |
O6—C4—C5—C5A | −166.0 (3) | C2A—C5A—C5B—O1 | 54.1 (3) |
O3—C4—C5—C5A | 15.0 (3) | C5—C5A—C5B—C1A | −123.8 (3) |
C4—C5—C5A—C5B | 92.1 (3) | C2A—C5A—C5B—C1A | −11.4 (3) |
C4—C5—C5A—C2A | −20.2 (3) |