8-Hydro­xy-(S)-3-methyl-1-oxoisochromane-5-carboxyl­ic acid (5-carboxy­mellein)

The mol­ecules of the title compound, C₁₁H₁₀O₅, are linked by a hydrogen bond involving the acid H and the carbonyl O atom of the di­hydro­isocoumarin unit into a linear chain running along the b axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.056
• wR factor = 0.127
• Data-to-parameter ratio = 5.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_731  Alert B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
                     O3   -H3O     1.555   1.555

PLAT_735  Alert B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Rat
                     O3   -H3O     1.555   1.555

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total                897
         Count of symmetry unique reflns          909
         Completeness (_total/calc)             98.68%
         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
          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.


 0 Alert Level A = Potentially serious problem

 2 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

8-Hydroxy-(S)-3-methyl-1-oxoisochromane-5-carboxylic acid

Crystal data

C11H10O5	F(000) = 232
Mr = 222.19	Dx = 1.530 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.3351 (4) Å	Cell parameters from 634 reflections
b = 9.0510 (5) Å	θ = 2.8–21.7°
c = 7.4211 (5) Å	µ = 0.12 mm^−1
β = 101.723 (3)°	T = 298 K
V = 482.41 (5) Å^3	Plate, colorless
Z = 2	0.15 × 0.12 × 0.06 mm

Data collection

Bruker APEX area-detector diffractometer	726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
φ and ω scans	h = −7→8
2438 measured reflections	k = −10→10
897 independent reflections	l = −8→6

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0712P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
897 reflections	Δρmax = 0.19 e Å^−3
151 parameters	Δρmin = −0.29 e Å^−3
3 restraints	Absolute structure: Calculation of Flack parameter suppressed by MERG 4.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0

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

	x	y	z	Uiso*/Ueq
O1	0.1754 (6)	0.4999 (4)	0.4401 (6)	0.051 (1)
O2	0.3626 (6)	0.5466 (5)	0.7055 (6)	0.060 (1)
O3	0.4325 (6)	−0.1346 (5)	0.7679 (5)	0.051 (1)
O4	0.1985 (6)	−0.2027 (5)	0.4657 (6)	0.050 (1)
O5	0.1254 (5)	−0.0469 (4)	0.2428 (5)	0.044 (1)
C1	0.2898 (7)	0.4602 (6)	0.5942 (7)	0.038 (1)
C2	0.3238 (7)	0.2995 (6)	0.6155 (7)	0.033 (1)
C3	0.4332 (9)	0.2578 (7)	0.7855 (7)	0.046 (2)
C4	0.4724 (7)	0.1131 (6)	0.8296 (7)	0.043 (2)
C5	0.3946 (8)	0.0033 (6)	0.7103 (8)	0.042 (2)
C6	0.2898 (7)	0.0413 (7)	0.5374 (7)	0.033 (1)
C7	0.2549 (7)	0.1905 (6)	0.4880 (6)	0.031 (1)
C8	0.2028 (7)	−0.0758 (7)	0.4124 (7)	0.038 (1)
C9	0.1390 (8)	0.2185 (6)	0.2988 (7)	0.039 (1)
C10	0.1635 (8)	0.0972 (6)	0.1676 (6)	0.038 (1)
C11	0.0335 (9)	0.1096 (9)	−0.0148 (8)	0.059 (2)
H1o	0.195 (8)	0.592 (2)	0.439 (9)	0.062*
H3o	0.373 (8)	−0.200 (6)	0.697 (8)	0.061*
H3	0.4804	0.3306	0.8706	0.055*
H4	0.5516	0.0888	0.9401	0.052*
H9a	0.0088	0.2251	0.3064	0.047*
H9b	0.1751	0.3120	0.2527	0.047*
H10	0.2920	0.0985	0.1491	0.046*
H11a	0.0566	0.0304	−0.0931	0.089*
H11b	0.0529	0.2025	−0.0705	0.089*
H11c	−0.0927	0.1041	0.0020	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.072 (3)	0.031 (2)	0.040 (2)	−0.001 (2)	−0.014 (2)	−0.007 (2)
O2	0.088 (3)	0.036 (2)	0.043 (2)	−0.004 (2)	−0.016 (2)	−0.006 (2)
O3	0.070 (3)	0.034 (3)	0.040 (2)	0.006 (2)	−0.007 (2)	0.004 (2)
O4	0.075 (3)	0.028 (3)	0.044 (2)	0.003 (2)	0.004 (2)	0.003 (2)
O5	0.065 (2)	0.031 (2)	0.029 (2)	−0.005 (2)	−0.009 (2)	−0.003 (2)
C1	0.052 (4)	0.029 (3)	0.031 (3)	−0.006 (3)	0.004 (3)	0.000 (3)
C2	0.042 (3)	0.030 (3)	0.024 (2)	−0.006 (3)	0.000 (2)	0.000 (2)
C3	0.056 (4)	0.042 (4)	0.034 (3)	−0.008 (3)	0.000 (3)	−0.008 (3)
C4	0.052 (3)	0.042 (4)	0.030 (3)	0.000 (3)	−0.004 (2)	0.010 (3)
C5	0.050 (4)	0.037 (4)	0.037 (3)	0.002 (3)	0.004 (3)	0.003 (3)
C6	0.037 (3)	0.032 (3)	0.029 (3)	0.004 (3)	0.001 (2)	−0.002 (2)
C7	0.033 (3)	0.034 (3)	0.025 (3)	0.002 (3)	0.002 (2)	0.004 (2)
C8	0.045 (3)	0.037 (4)	0.029 (3)	0.000 (3)	0.000 (2)	−0.004 (3)
C9	0.054 (3)	0.034 (3)	0.024 (3)	0.006 (3)	−0.004 (3)	0.006 (3)
C10	0.055 (3)	0.036 (3)	0.020 (2)	−0.002 (3)	−0.002 (2)	0.004 (2)
C11	0.067 (4)	0.067 (5)	0.032 (3)	0.007 (4)	−0.016 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C1	1.323 (6)	C7—C9	1.508 (7)
O2—C1	1.183 (6)	C9—C10	1.502 (7)
O3—C5	1.330 (7)	C10—C11	1.493 (7)
O4—C8	1.217 (7)	O1—H1o	0.85 (1)
O5—C8	1.298 (6)	O3—H3o	0.85 (1)
O5—C10	1.467 (6)	C3—H3	0.93
C1—C2	1.479 (8)	C4—H4	0.93
C2—C7	1.390 (7)	C9—H9a	0.97
C2—C3	1.402 (7)	C9—H9b	0.97
C3—C4	1.366 (8)	C10—H10	0.98
C4—C5	1.375 (8)	C11—H11a	0.96
C5—C6	1.398 (7)	C11—H11b	0.96
C6—C7	1.409 (8)	C11—H11c	0.96
C6—C8	1.467 (8)
C8—O5—C10	117.9 (4)	O5—C10—C9	110.2 (4)
O2—C1—O1	122.8 (5)	C11—C10—C9	113.2 (5)
O2—C1—C2	122.2 (5)	C1—O1—H1o	101 (4)
O1—C1—C2	115.0 (5)	C5—O3—H3o	114 (5)
C7—C2—C3	118.9 (5)	C4—C3—H3	119.1
C7—C2—C1	126.6 (5)	C2—C3—H3	119.1
C3—C2—C1	114.5 (5)	C3—C4—H4	120.0
C4—C3—C2	121.9 (5)	C5—C4—H4	120.0
C3—C4—C5	119.9 (5)	C10—C9—H9a	109.4
O3—C5—C4	116.0 (5)	C7—C9—H9a	109.4
O3—C5—C6	124.5 (5)	C10—C9—H9b	109.4
C4—C5—C6	119.4 (5)	C7—C9—H9b	109.4
C5—C6—C7	120.8 (5)	H9a—C9—H9b	108.0
C5—C6—C8	119.3 (5)	O5—C10—H10	109.1
C7—C6—C8	119.7 (5)	C11—C10—H10	109.1
C2—C7—C6	118.8 (5)	C9—C10—H10	109.1
C2—C7—C9	125.0 (5)	C10—C11—H11a	109.5
C6—C7—C9	116.2 (4)	C10—C11—H11b	109.5
O4—C8—O5	118.0 (5)	H11a—C11—H11b	109.5
O4—C8—C6	120.9 (6)	C10—C11—H11c	109.5
O5—C8—C6	121.1 (5)	H11a—C11—H11c	109.5
C10—C9—C7	111.2 (4)	H11b—C11—H11c	109.5
O5—C10—C11	106.0 (5)
O2—C1—C2—C7	−175.6 (5)	C5—C6—C7—C2	−1.1 (7)
O1—C1—C2—C7	3.1 (8)	C8—C6—C7—C2	173.8 (5)
O2—C1—C2—C3	6.2 (8)	C5—C6—C7—C9	−179.5 (5)
O1—C1—C2—C3	−175.1 (5)	C8—C6—C7—C9	−4.5 (7)
C7—C2—C3—C4	−0.6 (8)	C10—O5—C8—O4	−167.5 (5)
C1—C2—C3—C4	177.8 (5)	C10—O5—C8—C6	13.6 (7)
C2—C3—C4—C5	−4.0 (9)	C5—C6—C8—O4	10.3 (8)
C3—C4—C5—O3	−176.7 (5)	C7—C6—C8—O4	−164.7 (5)
C3—C4—C5—C6	5.9 (8)	C5—C6—C8—O5	−170.9 (5)
O3—C5—C6—C7	179.5 (5)	C7—C6—C8—O5	14.1 (7)
C4—C5—C6—C7	−3.4 (7)	C2—C7—C9—C10	152.6 (5)
O3—C5—C6—C8	4.5 (8)	C6—C7—C9—C10	−29.1 (6)
C4—C5—C6—C8	−178.4 (5)	C8—O5—C10—C11	−170.7 (5)
C3—C2—C7—C6	3.1 (7)	C8—O5—C10—C9	−47.8 (6)
C1—C2—C7—C6	−175.1 (5)	C7—C9—C10—O5	54.1 (6)
C3—C2—C7—C9	−178.7 (5)	C7—C9—C10—C11	172.6 (5)
C1—C2—C7—C9	3.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O4^i	0.85 (1)	1.87 (2)	2.702 (5)	168 (6)
O3—H3o···O4	0.85 (1)	1.92 (5)	2.606 (6)	137 (6)

Symmetry code: (i) x, y+1, z.