(8-Hy­droxy-6-meth­oxy-1-oxo-1H-isochromen-3-yl)methyl formate: a supra­molecular framework

In the title compound, C₁₂H₁₀O₆, an intra­molecular O—H...O hydrogen bond forms an S(6) ring motif. The mol­ecule is essentially planar with an r.m.s. deviation of 0.051 Å for all non-H atoms. In the crystal mol­ecules are linked by C—H...O hydrogen bonds and a C—H...π inter­action, forming a supra­molecular framework.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.050
• wR factor = 0.135
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.964 Why?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.63 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0066 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         28 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note

   0 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
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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

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Computing details

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2004); cell refinement: CELL in IPDS-I (Stoe & Cie, 2004); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

(8-Hydroxy-6-methoxy-1-oxo-1H-isochromen-3-yl)methyl formate

Crystal data

C12H10O6	Dx = 1.542 Mg m^−3
Mr = 250.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 3909 reflections
a = 25.006 (2) Å	θ = 2.2–25.8°
b = 5.0337 (6) Å	µ = 0.13 mm^−1
c = 8.5646 (6) Å	T = 173 K
V = 1078.05 (17) Å^3	Block, colorless
Z = 4	0.50 × 0.50 × 0.50 mm
F(000) = 520

Data collection

STOE IPDS 1 diffractometer	2012 independent reflections
Radiation source: fine-focus sealed tube	1249 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.070
φ rotation scans	θmax = 26.1°, θmin = 2.9°
Absorption correction: multi-scan (MULABS; Spek, 2020)	h = −30→30
Tmin = 0.763, Tmax = 1.000	k = −6→6
7630 measured reflections	l = −9→9

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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0852P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
2012 reflections	Δρmax = 0.32 e Å^−3
166 parameters	Δρmin = −0.27 e Å^−3
1 restraint	Extinction correction: (SHELXL-2018/3; Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Flack x = 0.223 (999) by classical fit to all intensities 1.664 (999) from 481 selected quotients (Parsons' method)

** Absolute structure cannot be determined reliably **

The hydroxyl H atom and the C-bound H atoms were included in calculated positions and treated as riding on their parent O or C atoms.

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

	x	y	z	Uiso*/Ueq
O1	0.68528 (13)	0.9547 (7)	−0.0918 (5)	0.0500 (9)
O2	0.75876 (11)	0.7819 (6)	0.0089 (4)	0.0461 (9)
O3	0.58898 (11)	0.0468 (7)	0.3437 (5)	0.0511 (10)
O4	0.59095 (13)	0.7730 (7)	−0.0142 (5)	0.0531 (10)
H40	0.613134	0.862673	−0.065697	0.080*
O5	0.86682 (12)	0.4224 (8)	0.1774 (5)	0.0657 (12)
O6	0.94909 (14)	0.5664 (9)	0.1136 (6)	0.0732 (13)
C1	0.70366 (17)	0.7848 (9)	−0.0037 (6)	0.0433 (11)
C3	0.78373 (18)	0.5948 (9)	0.1006 (7)	0.0428 (12)
C4	0.75774 (17)	0.4136 (9)	0.1838 (6)	0.0443 (12)
H4	0.776871	0.288244	0.245052	0.053*
C5	0.67032 (17)	0.2286 (9)	0.2657 (6)	0.0438 (11)
H5	0.687823	0.104223	0.331620	0.053*
C6	0.61467 (17)	0.2302 (9)	0.2549 (7)	0.0434 (12)
C7	0.58804 (17)	0.4147 (10)	0.1602 (7)	0.0455 (12)
H7	0.550100	0.414965	0.154550	0.055*
C8	0.61731 (18)	0.5950 (9)	0.0759 (6)	0.0437 (13)
C9	0.67425 (17)	0.5970 (9)	0.0848 (7)	0.0399 (11)
C10	0.69987 (16)	0.4093 (9)	0.1799 (7)	0.0411 (11)
C11	0.53177 (17)	0.0277 (11)	0.3310 (8)	0.0614 (15)
H11C	0.518847	−0.116607	0.397911	0.092*
H11B	0.521957	−0.008880	0.222346	0.092*
H11A	0.515514	0.195648	0.364158	0.092*
C12	0.84306 (18)	0.6344 (10)	0.0911 (7)	0.0493 (13)
H12B	0.855082	0.629778	−0.019002	0.059*
H12A	0.853189	0.807981	0.136752	0.059*
C13	0.92037 (19)	0.4136 (14)	0.1770 (10)	0.0726 (19)
H13	0.936777	0.272176	0.232693	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0486 (18)	0.0487 (18)	0.053 (2)	0.0019 (15)	−0.0012 (16)	0.0089 (19)
O2	0.0381 (16)	0.0448 (17)	0.055 (2)	−0.0039 (13)	−0.0010 (15)	0.0043 (17)
O3	0.0330 (15)	0.0564 (19)	0.064 (3)	−0.0051 (14)	0.0021 (16)	0.0138 (19)
O4	0.0425 (17)	0.055 (2)	0.062 (3)	0.0046 (16)	−0.0054 (17)	0.0109 (19)
O5	0.0318 (16)	0.076 (2)	0.089 (3)	−0.0021 (17)	−0.002 (2)	0.026 (2)
O6	0.040 (2)	0.099 (3)	0.080 (3)	−0.012 (2)	0.0013 (19)	0.016 (3)
C1	0.036 (2)	0.046 (3)	0.048 (3)	0.0014 (19)	0.001 (2)	−0.001 (2)
C3	0.035 (2)	0.045 (2)	0.048 (3)	0.003 (2)	−0.002 (2)	−0.002 (2)
C4	0.038 (2)	0.044 (2)	0.051 (3)	0.0004 (19)	−0.004 (2)	−0.002 (2)
C5	0.034 (2)	0.044 (2)	0.053 (3)	−0.001 (2)	−0.004 (2)	0.002 (2)
C6	0.038 (2)	0.039 (2)	0.053 (3)	−0.0005 (19)	0.002 (2)	0.001 (2)
C7	0.035 (2)	0.048 (2)	0.053 (4)	−0.003 (2)	−0.003 (2)	−0.002 (2)
C8	0.036 (2)	0.044 (3)	0.052 (4)	0.003 (2)	−0.002 (2)	0.001 (2)
C9	0.033 (2)	0.038 (2)	0.049 (3)	0.0002 (19)	−0.001 (2)	0.001 (2)
C10	0.035 (2)	0.041 (2)	0.048 (3)	0.0008 (18)	0.000 (2)	−0.001 (2)
C11	0.031 (2)	0.073 (3)	0.080 (4)	−0.011 (2)	−0.001 (3)	0.013 (3)
C12	0.036 (2)	0.055 (3)	0.057 (4)	0.000 (2)	−0.002 (2)	0.005 (3)
C13	0.031 (3)	0.088 (4)	0.098 (6)	0.000 (3)	−0.003 (3)	0.021 (4)

Geometric parameters (Å, º)

O1—C1	1.230 (6)	C5—C10	1.383 (7)
O2—C3	1.376 (6)	C5—C6	1.395 (6)
O2—C1	1.382 (5)	C5—H5	0.9500
O3—C6	1.358 (6)	C6—C7	1.401 (7)
O3—C11	1.438 (5)	C7—C8	1.371 (7)
O4—C8	1.354 (6)	C7—H7	0.9500
O4—H40	0.8400	C8—C9	1.426 (6)
O5—C13	1.340 (6)	C9—C10	1.402 (7)
O5—C12	1.428 (6)	C11—H11C	0.9800
O6—C13	1.184 (7)	C11—H11B	0.9800
C1—C9	1.417 (7)	C11—H11A	0.9800
C3—C4	1.327 (7)	C12—H12B	0.9900
C3—C12	1.499 (6)	C12—H12A	0.9900
C4—C10	1.447 (6)	C13—H13	0.9500
C4—H4	0.9500
C3—O2—C1	120.3 (4)	O4—C8—C9	120.8 (4)
C6—O3—C11	118.3 (4)	C7—C8—C9	120.6 (4)
C8—O4—H40	109.5	C10—C9—C1	121.5 (4)
C13—O5—C12	116.1 (4)	C10—C9—C8	118.8 (4)
O1—C1—O2	115.3 (4)	C1—C9—C8	119.6 (4)
O1—C1—C9	126.7 (4)	C5—C10—C9	120.5 (4)
O2—C1—C9	117.9 (4)	C5—C10—C4	122.1 (4)
C4—C3—O2	123.7 (4)	C9—C10—C4	117.4 (4)
C4—C3—C12	127.2 (5)	O3—C11—H11C	109.5
O2—C3—C12	109.1 (4)	O3—C11—H11B	109.5
C3—C4—C10	119.2 (5)	H11C—C11—H11B	109.5
C3—C4—H4	120.4	O3—C11—H11A	109.5
C10—C4—H4	120.4	H11C—C11—H11A	109.5
C10—C5—C6	119.6 (5)	H11B—C11—H11A	109.5
C10—C5—H5	120.2	O5—C12—C3	106.5 (4)
C6—C5—H5	120.2	O5—C12—H12B	110.4
O3—C6—C5	115.5 (4)	C3—C12—H12B	110.4
O3—C6—C7	123.4 (4)	O5—C12—H12A	110.4
C5—C6—C7	121.1 (4)	C3—C12—H12A	110.4
C8—C7—C6	119.3 (4)	H12B—C12—H12A	108.6
C8—C7—H7	120.3	O6—C13—O5	125.8 (6)
C6—C7—H7	120.3	O6—C13—H13	117.1
O4—C8—C7	118.6 (4)	O5—C13—H13	117.1
C3—O2—C1—O1	−178.0 (4)	O2—C1—C9—C8	179.5 (4)
C3—O2—C1—C9	2.3 (6)	O4—C8—C9—C10	179.9 (5)
C1—O2—C3—C4	−1.6 (7)	C7—C8—C9—C10	0.8 (8)
C1—O2—C3—C12	179.1 (4)	O4—C8—C9—C1	−1.0 (8)
O2—C3—C4—C10	−0.2 (8)	C7—C8—C9—C1	179.9 (5)
C12—C3—C4—C10	179.0 (5)	C6—C5—C10—C9	1.3 (8)
C11—O3—C6—C5	−176.5 (5)	C6—C5—C10—C4	−178.7 (5)
C11—O3—C6—C7	4.8 (8)	C1—C9—C10—C5	179.7 (5)
C10—C5—C6—O3	−179.7 (5)	C8—C9—C10—C5	−1.2 (8)
C10—C5—C6—C7	−1.0 (8)	C1—C9—C10—C4	−0.3 (8)
O3—C6—C7—C8	179.2 (5)	C8—C9—C10—C4	178.8 (5)
C5—C6—C7—C8	0.6 (8)	C3—C4—C10—C5	−178.9 (5)
C6—C7—C8—O4	−179.6 (5)	C3—C4—C10—C9	1.1 (8)
C6—C7—C8—C9	−0.5 (8)	C13—O5—C12—C3	176.8 (5)
O1—C1—C9—C10	179.0 (5)	C4—C3—C12—O5	5.5 (8)
O2—C1—C9—C10	−1.4 (7)	O2—C3—C12—O5	−175.2 (4)
O1—C1—C9—C8	−0.1 (8)	C12—O5—C13—O6	0.9 (12)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H40···O1	0.84	1.88	2.616 (5)	146
C4—H4···O1^i	0.95	2.38	3.326 (6)	173
C5—H5···O2^i	0.95	2.59	3.541 (6)	176
C7—H7···O6^ii	0.95	2.55	3.499 (5)	175
C11—H11C···O6^i	0.98	2.57	3.388 (8)	141
C12—H12B···Cg^iii	0.99	2.88	3.788 (6)	153

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