Dimethyl 2,3-dihydroxy­terephthalate

Huang, J.-Y.; Liang, H.-Z.

doi:10.1107/S1600536807022945

Dimethyl 2,3-dihydroxyterephthalate

J.-Y. Huang and H.-Z. Liang

The title compound, C₁₀H₁₀O₆, shows strong intramolecular O—H

O hydrogen bonds. Short intermolecular O

O weak interactions and weak intermolecular O—H

O hydrogen bonds link molecules into a supramolecular dimer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022945/rt2003sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022945/rt2003Isup2.hkl Contains datablock I

CCDC reference: 651514

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.112
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O1      ..       2.69 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.19 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      24.20 Deg.
              O3   -O5   -H5A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.90 Deg.
              O1   -O6   -H6B     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.80 Deg.
              O1   -O6   -H6B     3.776   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dimethyl 2,3-dihydroxyterephthalate top

Crystal data top

C₁₀H₁₀O₆	F(000) = 472
M_r = 226.18	D_x = 1.516 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2396 reflections
a = 4.8375 (10) Å	θ = 3.7–27.5°
b = 10.691 (2) Å	µ = 0.13 mm⁻¹
c = 19.179 (4) Å	T = 298 K
β = 92.39 (3)°	Platelet, colorless
V = 991.1 (3) Å³	0.43 × 0.35 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX II CCD diffractometer	2267 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.40 pixels mm^-1	θ_max = 27.5°, θ_min = 3.7°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.947, T_max = 0.987	l = −24→24
9475 measured reflections

Refinement top

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) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0521P)² + 0.0764P] where P = (F_o² + 2F_c²)/3
2267 reflections	(Δ/σ)_max = 0.002
145 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Special details top

Experimental. ¹H NMR (400 MHz, CDCl₃, 275 K, p.p.m.): δ 10.90 (2H, s), 7.32 (2H, s), 3.97 (6H, s).

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

	x	y	z	U_iso*/U_eq
O1	0.8923 (3)	0.89569 (12)	0.47051 (7)	0.0530 (4)
O2	0.7365 (3)	0.73378 (12)	0.40707 (6)	0.0515 (4)
O3	−0.0814 (3)	0.73071 (13)	0.71886 (7)	0.0582 (4)
O4	−0.1474 (3)	0.55492 (12)	0.65795 (6)	0.0530 (4)
O5	0.2824 (3)	0.89126 (12)	0.67687 (6)	0.0531 (4)
H5A	0.1646	0.8625	0.7036	0.080*
O6	0.6491 (2)	0.95178 (11)	0.58690 (6)	0.0491 (3)
H6B	0.7615	0.9639	0.5554	0.074*
C1	0.9261 (4)	0.7709 (2)	0.35399 (10)	0.0641 (6)
H1A	0.9113	0.7121	0.3148	0.096*
H1B	1.1159	0.7704	0.3740	0.096*
H1C	0.8790	0.8553	0.3374	0.096*
C2	−0.3314 (4)	0.5118 (2)	0.71086 (11)	0.0617 (6)
H2A	−0.4043	0.4291	0.6979	0.093*
H2B	−0.4851	0.5709	0.7144	0.093*
H2C	−0.2290	0.5063	0.7559	0.093*
C3	−0.0322 (3)	0.66596 (17)	0.66852 (9)	0.0413 (4)
C4	0.3834 (3)	0.65905 (16)	0.50735 (8)	0.0404 (4)
H4A	0.4053	0.6077	0.4675	0.049*
C5	0.7389 (3)	0.80703 (15)	0.46327 (8)	0.0385 (4)
C6	0.2013 (3)	0.62455 (15)	0.55666 (8)	0.0408 (4)
H6A	0.1018	0.5483	0.5516	0.049*
C7	0.5058 (3)	0.84595 (15)	0.57325 (8)	0.0361 (4)
C8	0.1615 (3)	0.70163 (15)	0.61457 (8)	0.0361 (4)
C9	0.5376 (3)	0.76958 (15)	0.51521 (8)	0.0358 (4)
C10	0.3097 (3)	0.81264 (15)	0.62259 (8)	0.0374 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0516 (7)	0.0494 (8)	0.0589 (8)	−0.0167 (6)	0.0112 (6)	−0.0036 (6)
O2	0.0562 (8)	0.0559 (8)	0.0434 (7)	−0.0143 (6)	0.0138 (6)	−0.0063 (6)
O3	0.0657 (9)	0.0607 (9)	0.0497 (8)	−0.0019 (7)	0.0181 (7)	−0.0076 (6)
O4	0.0581 (8)	0.0482 (8)	0.0542 (7)	−0.0098 (6)	0.0197 (6)	0.0045 (6)
O5	0.0590 (8)	0.0497 (8)	0.0515 (7)	−0.0066 (6)	0.0116 (6)	−0.0189 (6)
O6	0.0488 (7)	0.0415 (7)	0.0573 (7)	−0.0124 (6)	0.0070 (6)	−0.0099 (6)
C1	0.0688 (13)	0.0807 (16)	0.0443 (10)	−0.0134 (11)	0.0188 (10)	−0.0019 (10)
C2	0.0608 (12)	0.0611 (13)	0.0648 (12)	−0.0060 (10)	0.0227 (10)	0.0142 (11)
C3	0.0390 (9)	0.0430 (10)	0.0421 (9)	0.0032 (8)	0.0028 (7)	0.0052 (8)
C4	0.0467 (10)	0.0361 (9)	0.0388 (9)	−0.0027 (7)	0.0045 (8)	−0.0048 (7)
C5	0.0366 (8)	0.0350 (9)	0.0439 (9)	0.0002 (7)	−0.0004 (7)	0.0025 (7)
C6	0.0447 (9)	0.0341 (9)	0.0437 (9)	−0.0071 (7)	0.0028 (8)	−0.0015 (7)
C7	0.0317 (8)	0.0315 (8)	0.0446 (9)	0.0006 (6)	−0.0035 (7)	−0.0010 (7)
C8	0.0346 (8)	0.0376 (9)	0.0360 (8)	0.0021 (7)	0.0000 (7)	0.0010 (7)
C9	0.0325 (8)	0.0344 (9)	0.0404 (8)	0.0009 (7)	0.0006 (7)	0.0004 (7)
C10	0.0369 (8)	0.0360 (9)	0.0389 (8)	0.0050 (7)	−0.0029 (7)	−0.0055 (7)

Geometric parameters (Å, º) top

O1—C5	1.2082 (19)	C1—H1C	0.9800
O1—O6	2.6355 (17)	C2—H2A	0.9800
O2—C5	1.332 (2)	C2—H2B	0.9800
O2—C1	1.454 (2)	C2—H2C	0.9800
O3—C3	1.219 (2)	C3—C8	1.475 (2)
O3—O5	2.6097 (19)	C4—C6	1.369 (2)
O4—C3	1.323 (2)	C4—C9	1.402 (2)
O4—C2	1.452 (2)	C4—H4A	0.9500
O5—C10	1.3489 (18)	C5—C9	1.477 (2)
O5—H5A	0.8400	C6—C8	1.403 (2)
O6—C7	1.3469 (19)	C6—H6A	0.9500
O6—O1ⁱ	2.9994 (18)	C7—C9	1.394 (2)
O6—H6B	0.8400	C7—C10	1.413 (2)
C1—H1A	0.9800	C8—C10	1.392 (2)
C1—H1B	0.9800

C5—O1—O6	88.97 (10)	O3—C3—O4	122.40 (15)
C5—O2—C1	114.93 (14)	O3—C3—C8	124.00 (17)
C3—O3—O5	88.44 (11)	O4—C3—C8	113.60 (15)
C3—O4—C2	116.36 (14)	C6—C4—C9	120.48 (15)
C10—O5—O3	85.26 (10)	C6—C4—H4A	119.8
C10—O5—H5A	109.5	C9—C4—H4A	119.8
O3—O5—H5A	24.2	O1—C5—O2	122.61 (15)
C7—O6—O1	83.61 (9)	O1—C5—C9	123.66 (15)
C7—O6—O1ⁱ	140.17 (10)	O2—C5—C9	113.74 (14)
O1—O6—O1ⁱ	56.61 (5)	C4—C6—C8	120.13 (15)
C7—O6—H6B	109.5	C4—C6—H6A	119.9
O1—O6—H6B	25.9	C8—C6—H6A	119.9
O1ⁱ—O6—H6B	30.8	O6—C7—C9	125.02 (14)
O2—C1—H1A	109.5	O6—C7—C10	115.85 (14)
O2—C1—H1B	109.5	C9—C7—C10	119.12 (15)
H1A—C1—H1B	109.5	C10—C8—C6	120.10 (14)
O2—C1—H1C	109.5	C10—C8—C3	118.84 (14)
H1A—C1—H1C	109.5	C6—C8—C3	121.05 (15)
H1B—C1—H1C	109.5	C7—C9—C4	120.22 (14)
O4—C2—H2A	109.5	C7—C9—C5	118.53 (15)
O4—C2—H2B	109.5	C4—C9—C5	121.25 (14)
H2A—C2—H2B	109.5	O5—C10—C8	123.38 (14)
O4—C2—H2C	109.5	O5—C10—C7	116.74 (15)
H2A—C2—H2C	109.5	C8—C10—C7	119.86 (14)
H2B—C2—H2C	109.5

C3—O3—O5—C10	1.79 (13)	O4—C3—C8—C6	3.1 (2)
C5—O1—O6—C7	3.25 (13)	O6—C7—C9—C4	177.93 (15)
C5—O1—O6—O1ⁱ	−178.74 (14)	C10—C7—C9—C4	−2.1 (2)
O5—O3—C3—O4	176.36 (16)	O6—C7—C9—C5	−1.3 (2)
O5—O3—C3—C8	−2.68 (17)	C10—C7—C9—C5	178.67 (14)
C2—O4—C3—O3	−1.7 (3)	C6—C4—C9—C7	−0.4 (2)
C2—O4—C3—C8	177.42 (15)	C6—C4—C9—C5	178.78 (16)
O6—O1—C5—O2	175.49 (15)	O1—C5—C9—C7	5.4 (3)
O6—O1—C5—C9	−4.44 (16)	O2—C5—C9—C7	−174.56 (14)
C1—O2—C5—O1	−1.9 (2)	O1—C5—C9—C4	−173.79 (16)
C1—O2—C5—C9	178.03 (15)	O2—C5—C9—C4	6.3 (2)
C9—C4—C6—C8	1.9 (2)	O3—O5—C10—C8	−0.27 (15)
O1—O6—C7—C9	−0.93 (16)	O3—O5—C10—C7	−178.61 (14)
O1ⁱ—O6—C7—C9	−3.5 (3)	C6—C8—C10—O5	−179.96 (15)
O1—O6—C7—C10	179.14 (13)	C3—C8—C10—O5	−1.2 (2)
O1ⁱ—O6—C7—C10	176.56 (11)	C6—C8—C10—C7	−1.7 (2)
C4—C6—C8—C10	−0.9 (2)	C3—C8—C10—C7	177.12 (15)
C4—C6—C8—C3	−179.64 (15)	O6—C7—C10—O5	1.5 (2)
O3—C3—C8—C10	3.4 (3)	C9—C7—C10—O5	−178.44 (14)
O4—C3—C8—C10	−175.67 (14)	O6—C7—C10—C8	−176.91 (14)
O3—C3—C8—C6	−177.77 (16)	C9—C7—C10—C8	3.2 (2)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3	0.84	1.88	2.6097 (19)	145
O6—H6B···O1	0.84	1.91	2.6355 (17)	143
O6—H6B···O1ⁱ	0.84	2.32	2.9994 (18)	139