Crystal structure of 2,5-di­hydroxy­terephthalic acid from powder diffraction data

The crystal structure of anhydrous 2,5-dhy­droxy­terephthalic acid, C₈H₆O₆, was solved and refined using laboratory X-ray powder diffraction data, and optimized using density functional techniques.

Key indicators

• Single-crystal X-ray study
• T = 302 K
• Mean [sigma](C-C) = 0.013 Å
• Mean [sigma](C-C) = 0.000 Å
• R factor = 0.000
• wR factor = 0.000
• Data-to-parameter ratio = 0.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT198_ALERT_1_A Missing _diffrn_ambient_temperature   Datum ....     Please Add

Alert level B
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0125 Ang.

Alert level C
PLAT751_ALERT_4_C Bond    Calc     1.06000, Rep    1.060(8) ......  Senseless s.u.
              C7       -H8              1_555   1_555 ........     #    9 Check
PLAT751_ALERT_4_C Bond    Calc     0.99000, Rep    0.987(5) ......  Senseless s.u.
              O1       -H2              1_555   1_555 ........     #   14 Check
PLAT751_ALERT_4_C Bond    Calc     1.00000, Rep    1.004(6) ......  Senseless s.u.
              O3       -H4              1_555   1_555 ........     #   16 Check
PLAT751_ALERT_4_C Bond    Calc     1.06000, Rep    1.060(8) ......  Senseless s.u.
              H8       -C7              1_555   1_555 ........     #   18 Check
PLAT751_ALERT_4_C Bond    Calc     0.99000, Rep    0.987(5) ......  Senseless s.u.
              H2       -O1              1_555   1_555 ........     #   19 Check
PLAT751_ALERT_4_C Bond    Calc     1.00000, Rep    1.004(6) ......  Senseless s.u.
              H4       -O3              1_555   1_555 ........     #   20 Check
PLAT752_ALERT_4_C Angle   Calc      115.00, Rep   115.1(10) ......  Senseless s.u.
              C6      -C7      -H8         1_555  1_555  1_555     #    9 Check
PLAT752_ALERT_4_C Angle   Calc      105.00, Rep    105.5(6) ......  Senseless s.u.
              C6      -O1      -H2         1_555  1_555  1_555     #   13 Check
PLAT752_ALERT_4_C Angle   Calc      113.00, Rep    112.7(5) ......  Senseless s.u.
              C9      -O3      -H4         1_555  1_555  1_555     #   14 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...         42 Units
PLAT769_ALERT_4_G CIF Embedded explicitly supplied scattering data     Please Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         18 Note
PLAT981_ALERT_1_G No non-zero f" Anomalous Scattering Values Found     Please Check
PLAT986_ALERT_1_G No non-zero f' Anomalous Scattering Values Found     Please Check

   1 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   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
  10 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: Ia


Alert level A
PLAT198_ALERT_1_A Missing _diffrn_ambient_temperature   Datum ....     Please Add

Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit -F 4vw 2vw Check
PLAT741_ALERT_1_C Bond    Calc 1.55290(10), Rep     1.55289 ......    Missing s.u.
              C1       -C1              1_555   4_555 ........     #    1 Check
PLAT741_ALERT_1_C Bond    Calc 1.55290(10), Rep     1.55289 ......    Missing s.u.
              C1       -C1              1_555   5_555 ........     #    2 Check
PLAT741_ALERT_1_C Bond    Calc 1.55290(10), Rep     1.55289 ......    Missing s.u.
              C1       -C1              1_555   6_555 ........     #    3 Check
PLAT741_ALERT_1_C Bond    Calc 1.55290(10), Rep     1.55289 ......    Missing s.u.
              C1       -C1              1_555  25_555 ........     #    4 Check

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT040_ALERT_1_G No H-atoms in this Carbon Containing Compound ..     Please Check
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...         -2 Units
PLAT769_ALERT_4_G CIF Embedded explicitly supplied scattering data     Please Note
PLAT981_ALERT_1_G No non-zero f" Anomalous Scattering Values Found     Please Check
PLAT986_ALERT_1_G No non-zero f' Anomalous Scattering Values Found     Please Check

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

  10 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
   1 ALERT type 5 Informative message, check

# start Validation Reply Form
_vrf_PLAT198_I
;
PROBLEM: Missing _diffrn_ambient_temperature   Datum ....     Please Add
RESPONSE: ...
;
_vrf_PLAT198_Ia
;
PROBLEM: Missing _diffrn_ambient_temperature   Datum ....     Please Add
RESPONSE: ...
;
# end Validation Reply Form

---

Computing details

2,5-Dihydroxybenzene-1,4-dicarboxylic acid (I)

Crystal data

C8H6O6	β = 102.219 (4)°
Mr = 198.08	γ = 96.7621 (14)°
Triclinic, P1	V = 191.69 (1) Å^3
Hall symbol: -P 1	Z = 1
a = 4.2947 (5) Å	Dx = 1.716 Mg m^−3
b = 5.6089 (5) Å	T = 302 K
c = 8.2331 (19) Å	cylinder, 12 × 0.7 mm
α = 93.612 (4)°

Data collection

PANalytical Empyrean diffractometer	Data collection mode: transmission
Specimen mounting: glass capillary	Scan method: step

Refinement

18 restraints

Preferred orientation correction: Simple spherical harmonic correction Order = 4 Coefficients: 0:0:C(2,-2) = 0.246(11); 0:0:C(2,-1) = -0.018(11); 0:0:C(2,0) = -0.313(16); 0:0:C(2,1) = 0.217(13); 0:0:C(2,2) = -0.192(9); 0:0:C(4,-4) = -0.146(17); 0:0:C(4,-3) = 0.073(19); 0:0:C(4,-2) = -0.052(16); 0:0:C(4,-1) = 0.083(18); 0:0:C(4,0) = -0.058(17); 0:0:C(4,1) = -0.006(18); 0:0:C(4,2) = -0.196(23); 0:0:C(4,3) = 0.071(16); 0:0:C(4,4) = 0.108(25)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C10	0.492 (2)	0.6406 (16)	0.6392 (11)	0.0323 (10)*
C6	0.6818 (18)	0.4506 (18)	0.6571 (9)	0.0323 (10)*
C7	0.6946 (18)	0.3106 (14)	0.5107 (12)	0.0323 (10)*
C9	0.477 (2)	0.7892 (16)	0.7918 (9)	0.0553 (15)*
O1	0.8599 (12)	0.4082 (9)	0.8120 (6)	0.0323 (10)*
O3	0.2791 (12)	0.9640 (12)	0.7718 (7)	0.0553 (15)*
O5	0.6452 (16)	0.7744 (11)	0.9376 (9)	0.0553 (15)*
H8	0.84185	0.17135	0.52928	0.0420 (14)*
H2	0.83782	0.54288	0.88998	0.0420 (14)*
H4	0.30280	1.07255	0.87663	0.0719 (19)*

Geometric parameters (Å, º)

C10—C6	1.411 (5)	C9—O3	1.365 (5)
C10—C7^i	1.384 (5)	C9—O5	1.277 (5)
C10—C9	1.482 (6)	O1—C6	1.391 (5)
C6—C10	1.411 (5)	O1—H2	0.987 (5)
C6—C7	1.412 (6)	O3—C9	1.365 (5)
C6—O1	1.391 (5)	O3—H4	1.004 (6)
C7—C10^i	1.384 (5)	O5—C9	1.277 (5)
C7—C6	1.412 (6)	H8—C7	1.060 (8)
C7—H8	1.060 (8)	H2—O1	0.987 (5)
C9—C10	1.482 (6)	H4—O3	1.004 (6)
C6—C10—C7^i	124.3 (7)	C10^i—C7—H8	126.7 (10)
C6—C10—C9	118.1 (9)	C6—C7—H8	115.1 (10)
C7^i—C10—C9	117.5 (9)	C10—C9—O3	116.8 (7)
C10—C6—C7	117.4 (6)	C10—C9—O5	125.0 (9)
C10—C6—O1	121.6 (9)	O3—C9—O5	118.1 (7)
C7—C6—O1	121.0 (10)	C6—O1—H2	105.5 (6)
C10^i—C7—C6	118.1 (7)	C9—O3—H4	112.7 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

(Ia)

Crystal data

C	V = 46.12 (1) Å^3
Mr = 12.01	Z = 8
Cubic, Fd3m	Dx = 3.459 Mg m^−3
Hall symbol: -F 4vw 2vw	T = 302 K
a = 3.58625 (11) Å

Refinement

Preferred orientation correction: March-Dollase correction coef. = 1.000 axis = [0, 0, 1]

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.12500	0.12500	0.12500	0.0159*

Geometric parameters (Å, º)

C1—C1^i	1.5529	C1—C1^iii	1.5529
C1—C1^ii	1.5529	C1—C1^iv	1.5529
C1^i—C1—C1^ii	109.471	C1^i—C1—C1^iv	109.471
C1^i—C1—C1^iii	109.471	C1^ii—C1—C1^iv	109.471
C1^ii—C1—C1^iii	109.471	C1^iii—C1—C1^iv	109.471

Symmetry codes: (i) x+1/4, y+1/4, −z; (ii) −z, x+1/4, y+1/4; (iii) y+1/4, −z, x+1/4; (iv) −x, −y, −z.

(I_DFT)

Crystal data

C8H6O6	c = 8.1976 Å
Mr = 198.08	α = 93.6590°
Triclinic, P1	β = 102.1730°
a = 4.2647 Å	γ = 96.7840°
b = 5.5912 Å	Z = 1

Data collection

h = →	l = →
k = →

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C10	0.50725	0.65165	0.64068	0.06414*
C6	0.68695	0.46350	0.65571	0.06414*
C7	0.69097	0.31393	0.51546	0.06414*
C9	0.48403	0.80691	0.79069	0.01062*
O1	0.87656	0.42423	0.80458	0.01062*
O3	0.28942	0.97462	0.76830	0.01062*
O5	0.65017	0.78063	0.93109	0.01062*
H8	0.84185	0.17135	0.52928	0.08339*
H2	0.83782	0.54288	0.88999	0.01381*
H4	0.30280	1.07255	0.87663	0.01381*

Bond lengths (Å)

C10—C6	1.370	C7—H8	1.079
C10—C7^i	1.415	C9—O3	1.320
C10—C9	1.487	C9—O5	1.245
C6—C7	1.382	O1—H2	0.986
C6—O1	1.361	O3—H4	1.000
C7—C10^i	1.415	H4—O3	1.000

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H4···O5^ii	1.00	1.69	2.689	174
O1—H2···O5	0.99	1.68	2.567	147

Symmetry code: (ii) −x+1, −y+2, −z+2.

(DUSJUX_DFT)

Crystal data

C8H6O6·2(H2O)	c = 5.49900 Å
Monoclinic, P21/c	β = 103.03°
a = 5.18830 Å	V = 487.68 Å^3
b = 17.54500 Å	Z = 2

Data collection

h = →	l = →
k = →

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
O1	0.02829	0.35100	0.84164
H1	−0.08229	0.31915	0.93268
O2	0.41842	0.59430	0.63866
H2	0.51266	0.64044	0.56603
O3	0.28123	0.68492	0.87357
C1	0.01145	0.42401	0.92007
C2	0.14692	0.48106	0.82449
H3	0.26253	0.46707	0.68792
C3	0.28585	0.61663	0.80175
C4	0.13841	0.55682	0.90233
O4	0.64658	0.70011	0.46632
H4	0.52537	0.74263	0.39890
H5	0.75145	0.68680	0.34282

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	1.07	1.43	2.500	178
O1—H1···O3^i	1.01	1.64	2.562	149
O4—H4···O3^ii	0.99	1.78	2.736	161
O4—H5···O1^iii	0.99	1.82	2.794	169

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1.