Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705595X/su2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705595X/su2016Isup2.hkl |
CCDC reference: 674088
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.084
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
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 27.29 From the CIF: _reflns_number_total 843 Count of symmetry unique reflns 851 Completeness (_total/calc) 99.06% 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Kretz et al. (2006, 2007); Lerner et al. (2006); Margraf et al. (2006).
Commercially available 2,5-dihydroxybenzaldehyde (1.38 g) was recrystallized from toluene (20 ml).
H atoms bonded to C were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.93 Å. The H atoms bonded to O were refined isotropically. In the final cycles of refinement, in the absence of significant anomalous scattering effects, Friedel pairs were merged and Δf" set to zero.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997 and PLATON (Spek, 2003).
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. |
C7H6O3 | F(000) = 288 |
Mr = 138.12 | Dx = 1.448 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 11598 reflections |
a = 6.7544 (7) Å | θ = 3.8–27.4° |
b = 8.2240 (9) Å | µ = 0.12 mm−1 |
c = 11.4040 (13) Å | T = 173 K |
V = 633.47 (12) Å3 | Block, yellow |
Z = 4 | 0.49 × 0.32 × 0.29 mm |
Stoe IPDS II two-circle diffractometer | 797 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
Graphite monochromator | θmax = 27.3°, θmin = 3.9° |
ω scans | h = −8→8 |
7904 measured reflections | k = −10→10 |
843 independent reflections | l = −14→14 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.0216P] where P = (Fo2 + 2Fc2)/3 |
843 reflections | (Δ/σ)max < 0.001 |
99 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C7H6O3 | V = 633.47 (12) Å3 |
Mr = 138.12 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.7544 (7) Å | µ = 0.12 mm−1 |
b = 8.2240 (9) Å | T = 173 K |
c = 11.4040 (13) Å | 0.49 × 0.32 × 0.29 mm |
Stoe IPDS II two-circle diffractometer | 797 reflections with I > 2σ(I) |
7904 measured reflections | Rint = 0.064 |
843 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.23 e Å−3 |
843 reflections | Δρmin = −0.13 e Å−3 |
99 parameters |
Experimental. ; |
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 | ||
C1 | 0.1189 (2) | 0.78697 (16) | 0.40573 (13) | 0.0313 (3) | |
C2 | 0.11078 (18) | 0.80898 (15) | 0.52767 (12) | 0.0291 (3) | |
C3 | 0.1003 (2) | 0.67401 (16) | 0.60198 (12) | 0.0303 (3) | |
H3 | 0.0964 | 0.6895 | 0.6845 | 0.036* | |
C4 | 0.0956 (2) | 0.51869 (15) | 0.55672 (12) | 0.0306 (3) | |
C5 | 0.1033 (2) | 0.49826 (15) | 0.43446 (12) | 0.0324 (3) | |
H5 | 0.0997 | 0.3916 | 0.4025 | 0.039* | |
C6 | 0.1159 (2) | 0.62973 (16) | 0.36011 (12) | 0.0335 (3) | |
H6 | 0.1225 | 0.6133 | 0.2777 | 0.040* | |
O1 | 0.13038 (18) | 0.91338 (14) | 0.32977 (10) | 0.0418 (3) | |
H1 | 0.119 (3) | 1.005 (3) | 0.384 (2) | 0.064 (7)* | |
O4 | 0.0787 (2) | 0.39039 (12) | 0.63213 (10) | 0.0435 (3) | |
H4 | 0.097 (4) | 0.301 (3) | 0.581 (2) | 0.070 (7)* | |
C21 | 0.1097 (2) | 0.97036 (17) | 0.57875 (14) | 0.0350 (3) | |
H21 | 0.1055 | 0.9793 | 0.6618 | 0.042* | |
O21 | 0.11390 (18) | 1.09707 (11) | 0.52045 (11) | 0.0424 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0284 (6) | 0.0292 (6) | 0.0363 (7) | −0.0003 (6) | −0.0025 (5) | 0.0039 (5) |
C2 | 0.0263 (5) | 0.0247 (6) | 0.0363 (7) | 0.0001 (6) | −0.0010 (5) | −0.0004 (5) |
C3 | 0.0330 (6) | 0.0271 (6) | 0.0307 (6) | 0.0008 (5) | −0.0015 (5) | −0.0021 (5) |
C4 | 0.0320 (6) | 0.0243 (6) | 0.0356 (6) | 0.0006 (5) | −0.0012 (5) | 0.0025 (5) |
C5 | 0.0341 (6) | 0.0262 (6) | 0.0371 (6) | 0.0005 (5) | −0.0014 (5) | −0.0061 (5) |
C6 | 0.0346 (6) | 0.0351 (7) | 0.0306 (6) | −0.0011 (6) | 0.0001 (6) | −0.0032 (5) |
O1 | 0.0508 (6) | 0.0349 (5) | 0.0396 (5) | −0.0017 (5) | −0.0021 (5) | 0.0118 (4) |
O4 | 0.0649 (8) | 0.0240 (5) | 0.0416 (5) | 0.0002 (5) | −0.0014 (5) | 0.0041 (4) |
C21 | 0.0347 (6) | 0.0252 (6) | 0.0449 (7) | 0.0011 (6) | 0.0012 (6) | −0.0036 (5) |
O21 | 0.0462 (5) | 0.0231 (5) | 0.0580 (7) | 0.0010 (4) | 0.0009 (5) | 0.0017 (5) |
C1—O1 | 1.3554 (16) | C4—C5 | 1.405 (2) |
C1—C6 | 1.3941 (17) | C5—C6 | 1.3766 (19) |
C1—C2 | 1.4034 (18) | C5—H5 | 0.9500 |
C2—C3 | 1.3982 (19) | C6—H6 | 0.9500 |
C2—C21 | 1.4494 (17) | O1—H1 | 0.98 (2) |
C3—C4 | 1.3781 (17) | O4—H4 | 0.95 (3) |
C3—H3 | 0.9500 | C21—O21 | 1.2364 (18) |
C4—O4 | 1.3660 (16) | C21—H21 | 0.9500 |
O1—C1—C6 | 118.28 (12) | C6—C5—C4 | 121.30 (11) |
O1—C1—C2 | 122.45 (12) | C6—C5—H5 | 119.4 |
C6—C1—C2 | 119.27 (12) | C4—C5—H5 | 119.4 |
C3—C2—C1 | 120.01 (12) | C5—C6—C1 | 119.97 (12) |
C3—C2—C21 | 118.89 (12) | C5—C6—H6 | 120.0 |
C1—C2—C21 | 121.10 (12) | C1—C6—H6 | 120.0 |
C4—C3—C2 | 120.66 (12) | C1—O1—H1 | 100.7 (14) |
C4—C3—H3 | 119.7 | C4—O4—H4 | 101.5 (16) |
C2—C3—H3 | 119.7 | O21—C21—C2 | 123.75 (13) |
O4—C4—C3 | 118.82 (12) | O21—C21—H21 | 118.1 |
O4—C4—C5 | 122.37 (12) | C2—C21—H21 | 118.1 |
C3—C4—C5 | 118.79 (12) | ||
O1—C1—C2—C3 | −179.61 (11) | O4—C4—C5—C6 | 178.53 (12) |
C6—C1—C2—C3 | 0.2 (2) | C3—C4—C5—C6 | 0.2 (2) |
O1—C1—C2—C21 | 1.4 (2) | C4—C5—C6—C1 | −0.7 (2) |
C6—C1—C2—C21 | −178.79 (12) | O1—C1—C6—C5 | −179.65 (12) |
C1—C2—C3—C4 | −0.8 (2) | C2—C1—C6—C5 | 0.5 (2) |
C21—C2—C3—C4 | 178.24 (13) | C3—C2—C21—O21 | −178.30 (13) |
C2—C3—C4—O4 | −177.85 (12) | C1—C2—C21—O21 | 0.7 (2) |
C2—C3—C4—C5 | 0.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O21i | 0.95 (3) | 1.82 (3) | 2.7382 (15) | 163 (2) |
O1—H1···O21 | 0.98 (2) | 1.73 (3) | 2.6501 (16) | 155 (2) |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H6O3 |
Mr | 138.12 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 6.7544 (7), 8.2240 (9), 11.4040 (13) |
V (Å3) | 633.47 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.49 × 0.32 × 0.29 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7904, 843, 797 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.645 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.084, 1.11 |
No. of reflections | 843 |
No. of parameters | 99 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.13 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997 and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O21i | 0.95 (3) | 1.82 (3) | 2.7382 (15) | 163 (2) |
O1—H1···O21 | 0.98 (2) | 1.73 (3) | 2.6501 (16) | 155 (2) |
Symmetry code: (i) x, y−1, z. |
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Recently, we have extended our studies to redox-active ligands which can be used to influence the electrochemical reactivity of transition metals since their redox activity is expanded upon complexation (Lerner et al., 2006; Kretz et al., 2007). The resulting complexes can undergo multi-electron transfer reactions which are the sum of the oxidation state changes of the metal center and the ligand (Margraf et al., 2006; Kretz et al., 2006). Due to their electrochemical reversibility, hydroquinone / quinone derivatives are candidates for redox-active ligands (Lerner et al., 2006; Kretz et al., 2007). In our studies we have used Schiff-Base derivatives which can conveniently be achieved by reaction of amines and aldehyde derivatives (Margraf et al., 2006; Kretz et al., 2007). Thereby 2,5-dihydroxybenzaldehyde represents one of the starting materials. Single crystals of 2,5-dihydroxybenzaldehyde were obtained by recrystallization from toluene.
The title compound, C7H6O3, features a planar molecule (r.m.s. deviation for all non-H atoms 0.019 Å). Geometric parameters are in the usual ranges. Whereas one hydroxyl group forms an intramolecular hydrogen bond with the carbonyl group, the other one forms an intermolecular hydrogen bond with the carbonyl group of a symmetry equivalent molecule. The molecules crystallize in planes parallel to the bc plane.