Methyl 8-hydroxy-(S)-3-methyl-1-oxoisochromane-5-carboxyl­ate (5-methoxy­carbonyl­mellein)

The title compound, C₁₂H₁₂O₅, exists as two independent, relatively planar mol­ecules in the asymmetric unit; these differ in the orientation of the ester group.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.051
• wR factor = 0.123
• Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               2154
         Count of symmetry unique reflns         2155
         Completeness (_total/calc)             99.95%
         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.

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; 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.

Methyl 8-hydroxy-(S)-3-methyl-1-oxo-isochromane-5-carboxylate

Crystal data

C12H12O5	F(000) = 496
Mr = 236.22	Dx = 1.398 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9633 (7) Å	Cell parameters from 2648 reflections
b = 7.1890 (5) Å	θ = 2.5–23.7°
c = 14.425 (1) Å	µ = 0.11 mm^−1
β = 99.088 (1)°	T = 298 K
V = 1122.7 (1) Å^3	Needle, colorless
Z = 4	0.53 × 0.19 × 0.11 mm

Data collection

Bruker AXS area-detector diffractometer	1700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
φ and ω scans	h = −12→13
8222 measured reflections	k = −8→8
2154 independent reflections	l = −16→17

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)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.069P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2154 reflections	Δρmax = 0.18 e Å^−3
309 parameters	Δρmin = −0.18 e Å^−3
1 restraint	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
O1a	0.1124 (3)	0.4999 (5)	0.6625 (2)	0.077 (1)
O2a	0.1380 (3)	0.5214 (7)	0.8156 (2)	0.101 (1)
O3a	0.6899 (3)	0.6521 (8)	0.7795 (2)	0.098 (1)
O4a	0.6744 (3)	0.6316 (5)	0.5996 (2)	0.071 (1)
O5a	0.4977 (3)	0.6341 (5)	0.5074 (2)	0.056 (1)
C1a	−0.0178 (4)	0.4653 (9)	0.6593 (4)	0.088 (2)
C2a	0.1806 (4)	0.5259 (6)	0.7453 (3)	0.060 (1)
C3a	0.3133 (4)	0.5603 (6)	0.7431 (3)	0.050 (1)
C4a	0.3863 (4)	0.5739 (7)	0.8306 (3)	0.066 (1)
C5a	0.5099 (4)	0.6048 (9)	0.8418 (3)	0.075 (2)
C6a	0.5681 (4)	0.6260 (8)	0.7638 (3)	0.063 (1)
C7a	0.4970 (3)	0.6143 (6)	0.6743 (3)	0.050 (1)
C8a	0.3687 (3)	0.5825 (5)	0.6631 (2)	0.044 (1)
C9a	0.3045 (3)	0.5693 (7)	0.5634 (2)	0.051 (1)
C10a	0.3670 (3)	0.6817 (6)	0.4978 (3)	0.047 (1)
C11a	0.3147 (4)	0.6541 (8)	0.3962 (3)	0.067 (1)
C12a	0.5621 (4)	0.6278 (6)	0.5927 (3)	0.052 (1)
O1b	0.4391 (3)	0.6033 (6)	0.1957 (2)	0.084 (1)
O2b	0.5196 (3)	0.5765 (8)	0.0678 (2)	0.104 (2)
O3b	0.9688 (3)	0.4868 (6)	0.4095 (2)	0.079 (1)
O4b	1.0793 (3)	0.4120 (6)	0.2699 (2)	0.084 (1)
O5b	0.9985 (3)	0.4847 (5)	0.1266 (2)	0.073 (1)
C1b	0.3190 (4)	0.618 (1)	0.1384 (4)	0.113 (3)
C2b	0.5343 (4)	0.5818 (7)	0.1513 (3)	0.060 (1)
C3b	0.6521 (3)	0.5661 (6)	0.2157 (3)	0.047 (1)
C4b	0.6543 (4)	0.5808 (7)	0.3119 (3)	0.055 (1)
C5b	0.7589 (4)	0.5598 (6)	0.3755 (3)	0.054 (1)
C6b	0.8683 (4)	0.5180 (6)	0.3445 (3)	0.055 (1)
C7b	0.8713 (4)	0.5077 (6)	0.2479 (3)	0.050 (1)
C8b	0.7634 (3)	0.5321 (6)	0.1834 (3)	0.049 (1)
C9b	0.7770 (4)	0.5170 (8)	0.0819 (3)	0.064 (1)
C10b	0.9012 (4)	0.5847 (8)	0.0650 (3)	0.064 (1)
C11b	0.9244 (4)	0.5530 (9)	−0.0334 (3)	0.082 (2)
C12b	0.9888 (4)	0.4651 (7)	0.2161 (3)	0.060 (1)
H3a	0.7156	0.6586	0.7292	0.118*
H1aa	−0.0562	0.4485	0.5953	0.131*
H1ab	−0.0549	0.5693	0.6860	0.131*
H1ac	−0.0289	0.3550	0.6946	0.131*
H4a	0.3489	0.5614	0.8839	0.079*
H5a	0.5556	0.6116	0.9018	0.090*
H9aa	0.3020	0.4402	0.5438	0.062*
H9ab	0.2200	0.6121	0.5600	0.062*
H10a	0.3599	0.8135	0.5133	0.056*
H11a	0.3592	0.7300	0.3581	0.101*
H11b	0.2291	0.6891	0.3857	0.101*
H11c	0.3223	0.5257	0.3798	0.101*
H3b	1.0270	0.4566	0.3833	0.095*
H1ba	0.2571	0.6331	0.1780	0.169*
H1bb	0.3023	0.5063	0.1018	0.169*
H1bc	0.3177	0.7227	0.0972	0.169*
H4b	0.5808	0.6061	0.3338	0.066*
H5b	0.7567	0.5736	0.4393	0.065*
H9ba	0.7129	0.5897	0.0444	0.076*
H9bb	0.7665	0.3882	0.0622	0.076*
H10b	0.9083	0.7179	0.0792	0.077*
H11d	1.0037	0.6029	−0.0403	0.123*
H11e	0.8614	0.6138	−0.0766	0.123*
H11f	0.9231	0.4220	−0.0463	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1a	0.053 (2)	0.103 (3)	0.078 (2)	−0.013 (2)	0.026 (2)	0.001 (2)
O2a	0.088 (2)	0.155 (4)	0.072 (2)	−0.011 (3)	0.049 (2)	0.007 (3)
O3a	0.052 (2)	0.175 (4)	0.066 (2)	0.000 (2)	0.008 (2)	0.007 (3)
O4a	0.047 (2)	0.105 (3)	0.066 (2)	−0.005 (2)	0.020 (1)	−0.006 (2)
O5a	0.051 (2)	0.076 (2)	0.043 (2)	0.002 (2)	0.017 (1)	−0.004 (2)
C1a	0.052 (3)	0.109 (5)	0.106 (4)	−0.013 (3)	0.028 (3)	0.000 (4)
C2a	0.070 (3)	0.055 (3)	0.060 (3)	0.001 (2)	0.032 (2)	0.009 (2)
C3a	0.059 (2)	0.046 (2)	0.048 (2)	0.006 (2)	0.021 (2)	0.003 (2)
C4a	0.084 (3)	0.073 (3)	0.047 (3)	0.007 (3)	0.031 (2)	0.011 (2)
C5a	0.069 (3)	0.112 (4)	0.041 (2)	0.008 (3)	0.000 (2)	0.005 (3)
C6a	0.062 (3)	0.085 (4)	0.043 (3)	0.012 (3)	0.010 (2)	0.001 (2)
C7a	0.051 (2)	0.053 (3)	0.047 (2)	0.008 (2)	0.015 (2)	−0.001 (2)
C8a	0.051 (2)	0.038 (2)	0.046 (2)	0.005 (2)	0.019 (2)	0.005 (2)
C9a	0.052 (2)	0.060 (3)	0.044 (2)	−0.002 (2)	0.014 (2)	−0.007 (2)
C10a	0.048 (2)	0.048 (2)	0.047 (2)	0.006 (2)	0.015 (2)	0.000 (2)
C11a	0.069 (3)	0.089 (4)	0.046 (3)	0.015 (3)	0.014 (2)	0.003 (2)
C12a	0.051 (2)	0.054 (3)	0.052 (3)	−0.002 (2)	0.015 (2)	−0.004 (2)
O1b	0.054 (2)	0.142 (3)	0.060 (2)	0.018 (2)	0.023 (2)	0.010 (2)
O2b	0.065 (2)	0.202 (5)	0.045 (2)	0.018 (3)	0.013 (2)	0.006 (3)
O3b	0.069 (2)	0.114 (3)	0.052 (2)	−0.004 (2)	0.001 (2)	−0.002 (2)
O4b	0.049 (2)	0.132 (3)	0.067 (2)	0.001 (2)	0.002 (2)	−0.009 (2)
O5b	0.054 (2)	0.108 (3)	0.060 (2)	−0.006 (2)	0.022 (2)	−0.007 (2)
C1b	0.054 (3)	0.205 (8)	0.079 (4)	0.022 (4)	0.012 (2)	0.020 (5)
C2b	0.063 (3)	0.070 (3)	0.053 (3)	0.002 (2)	0.023 (2)	0.007 (2)
C3b	0.055 (2)	0.045 (2)	0.045 (2)	0.001 (2)	0.021 (2)	0.004 (2)
C4b	0.060 (3)	0.058 (3)	0.053 (2)	−0.011 (2)	0.024 (2)	0.000 (2)
C5b	0.073 (3)	0.054 (3)	0.039 (2)	−0.013 (2)	0.019 (2)	−0.003 (2)
C6b	0.060 (3)	0.059 (3)	0.044 (2)	−0.013 (2)	0.008 (2)	0.000 (2)
C7b	0.049 (2)	0.053 (3)	0.051 (2)	−0.007 (2)	0.017 (2)	−0.001 (2)
C8b	0.053 (2)	0.048 (3)	0.047 (2)	−0.008 (2)	0.015 (2)	−0.004 (2)
C9b	0.056 (3)	0.090 (4)	0.048 (2)	−0.003 (3)	0.020 (2)	0.000 (3)
C10b	0.059 (3)	0.077 (3)	0.062 (3)	−0.005 (3)	0.026 (2)	−0.004 (3)
C11b	0.076 (3)	0.114 (5)	0.064 (3)	0.005 (3)	0.039 (2)	0.005 (3)
C12b	0.053 (3)	0.074 (3)	0.056 (3)	−0.013 (2)	0.011 (2)	−0.013 (2)

Geometric parameters (Å, º)

O1a—C2a	1.319 (5)	C6b—C7b	1.401 (5)
O1a—C1a	1.443 (5)	C7b—C8b	1.396 (5)
O2a—C2a	1.182 (5)	C7b—C12b	1.467 (6)
O3a—C6a	1.332 (5)	C8b—C9b	1.499 (5)
O4a—C12a	1.219 (4)	C9b—C10b	1.501 (5)
O5a—C12a	1.320 (5)	C10b—C11b	1.498 (6)
O5a—C10a	1.458 (5)	O3a—H3a	0.82
C2a—C3a	1.481 (5)	C1a—H1aa	0.96
C3a—C4a	1.387 (6)	C1a—H1ab	0.96
C3a—C8a	1.396 (5)	C1a—H1ac	0.96
C4a—C5a	1.358 (6)	C4a—H4a	0.93
C5a—C6a	1.387 (6)	C5a—H5a	0.93
C6a—C7a	1.401 (5)	C9a—H9aa	0.97
C7a—C8a	1.409 (5)	C9a—H9ab	0.97
C7a—C12a	1.473 (5)	C10a—H10a	0.98
C8a—C9a	1.501 (5)	C11a—H11a	0.96
C9a—C10a	1.491 (5)	C11a—H11b	0.96
C10a—C11a	1.500 (5)	C11a—H11c	0.96
O1b—C2b	1.318 (5)	O3b—H3b	0.82
O1b—C1b	1.444 (5)	C1b—H1ba	0.96
O2b—C2b	1.191 (5)	C1b—H1bb	0.96
O3b—C6b	1.348 (5)	C1b—H1bc	0.96
O4b—C12b	1.220 (5)	C4b—H4b	0.93
O5b—C12b	1.319 (5)	C5b—H5b	0.93
O5b—C10b	1.465 (6)	C9b—H9ba	0.97
C2b—C3b	1.471 (5)	C9b—H9bb	0.97
C3b—C4b	1.388 (5)	C10b—H10b	0.98
C3b—C8b	1.394 (5)	C11b—H11d	0.96
C4b—C5b	1.359 (6)	C11b—H11e	0.96
C5b—C6b	1.377 (6)	C11b—H11f	0.96
C2a—O1a—C1a	118.0 (3)	O5b—C12b—C7b	119.6 (4)
C12a—O5a—C10a	118.0 (3)	C6a—O3a—H3a	109.5
O1a—C2a—O2a	121.9 (4)	O1a—C1a—H1aa	109.5
O1a—C2a—C3a	115.0 (3)	O1a—C1a—H1ab	109.5
O2a—C2a—C3a	123.1 (5)	H1aa—C1a—H1ab	109.5
C4a—C3a—C8a	118.7 (4)	O1a—C1a—H1ac	109.5
C4a—C3a—C2a	114.8 (4)	H1aa—C1a—H1ac	109.5
C8a—C3a—C2a	126.5 (4)	H1ab—C1a—H1ac	109.5
C5a—C4a—C3a	122.8 (4)	C5a—C4a—H4a	118.6
C4a—C5a—C6a	120.0 (4)	C3a—C4a—H4a	118.6
O3a—C6a—C5a	117.1 (4)	C4a—C5a—H5a	120.0
O3a—C6a—C7a	124.2 (4)	C6a—C5a—H5a	120.0
C5a—C6a—C7a	118.7 (4)	C10a—C9a—H9aa	109.1
C6a—C7a—C8a	121.0 (3)	C8a—C9a—H9aa	109.1
C6a—C7a—C12a	117.6 (4)	C10a—C9a—H9ab	109.1
C8a—C7a—C12a	121.4 (4)	C8a—C9a—H9ab	109.1
C3a—C8a—C7a	118.8 (3)	H9aa—C9a—H9ab	107.9
C3a—C8a—C9a	125.8 (3)	O5a—C10a—H10a	108.5
C7a—C8a—C9a	115.4 (3)	C9a—C10a—H10a	108.5
C10a—C9a—C8a	112.4 (3)	C11a—C10a—H10a	108.5
O5a—C10a—C9a	110.9 (3)	C10a—C11a—H11a	109.5
O5a—C10a—C11a	106.2 (3)	C10a—C11a—H11b	109.5
C9a—C10a—C11a	113.9 (4)	H11a—C11a—H11b	109.5
O4a—C12a—O5a	117.3 (3)	C10a—C11a—H11c	109.5
O4a—C12a—C7a	123.2 (4)	H11a—C11a—H11c	109.5
O5a—C12a—C7a	119.5 (4)	H11b—C11a—H11c	109.5
C2b—O1b—C1b	116.8 (3)	C6b—O3b—H3b	109.5
C12b—O5b—C10b	118.9 (3)	O1b—C1b—H1ba	109.5
O1b—C2b—O2b	120.3 (4)	O1b—C1b—H1bb	109.5
O1b—C2b—C3b	112.7 (3)	H1ba—C1b—H1bb	109.5
O2b—C2b—C3b	126.9 (4)	O1b—C1b—H1bc	109.5
C4b—C3b—C8b	118.0 (4)	H1ba—C1b—H1bc	109.5
C4b—C3b—C2b	120.0 (3)	H1bb—C1b—H1bc	109.5
C8b—C3b—C2b	122.0 (3)	C5b—C4b—H4b	118.4
C5b—C4b—C3b	123.1 (4)	C3b—C4b—H4b	118.4
C4b—C5b—C6b	119.4 (4)	C4b—C5b—H5b	120.3
O3b—C6b—C5b	117.9 (4)	C6b—C5b—H5b	120.3
O3b—C6b—C7b	122.5 (4)	C8b—C9b—H9ba	109.3
C5b—C6b—C7b	119.5 (4)	C10b—C9b—H9ba	109.3
C8b—C7b—C6b	120.4 (3)	C8b—C9b—H9bb	109.3
C8b—C7b—C12b	120.8 (4)	C10b—C9b—H9bb	109.3
C6b—C7b—C12b	118.8 (4)	H9ba—C9b—H9bb	108.0
C3b—C8b—C7b	119.6 (3)	O5b—C10b—H10b	109.1
C3b—C8b—C9b	124.5 (4)	C11b—C10b—H10b	109.1
C7b—C8b—C9b	115.9 (3)	C9b—C10b—H10b	109.1
C8b—C9b—C10b	111.6 (3)	C10b—C11b—H11d	109.5
O5b—C10b—C11b	106.5 (4)	C10b—C11b—H11e	109.5
O5b—C10b—C9b	109.5 (4)	H11d—C11b—H11e	109.5
C11b—C10b—C9b	113.5 (4)	C10b—C11b—H11f	109.5
O4b—C12b—O5b	118.2 (4)	H11d—C11b—H11f	109.5
O4b—C12b—C7b	122.2 (4)	H11e—C11b—H11f	109.5
C1a—O1a—C2a—O2a	0.1 (7)	C1b—O1b—C2b—O2b	0.7 (9)
C1a—O1a—C2a—C3a	179.9 (4)	C1b—O1b—C2b—C3b	−179.2 (5)
O2a—C2a—C3a—C4a	4.4 (7)	O2b—C2b—C3b—C4b	178.0 (6)
O1a—C2a—C3a—C4a	−175.5 (4)	O1b—C2b—C3b—C4b	−2.1 (6)
O2a—C2a—C3a—C8a	−174.5 (5)	O2b—C2b—C3b—C8b	−3.6 (8)
O1a—C2a—C3a—C8a	5.7 (6)	O1b—C2b—C3b—C8b	176.3 (4)
C8a—C3a—C4a—C5a	−1.2 (7)	C8b—C3b—C4b—C5b	−1.4 (6)
C2a—C3a—C4a—C5a	179.9 (5)	C2b—C3b—C4b—C5b	177.1 (4)
C3a—C4a—C5a—C6a	0.7 (9)	C3b—C4b—C5b—C6b	−1.5 (7)
C4a—C5a—C6a—O3a	−178.7 (6)	C4b—C5b—C6b—O3b	−176.0 (4)
C4a—C5a—C6a—C7a	−0.2 (8)	C4b—C5b—C6b—C7b	3.4 (7)
O3a—C6a—C7a—C8a	178.6 (5)	O3b—C6b—C7b—C8b	176.8 (4)
C5a—C6a—C7a—C8a	0.3 (7)	C5b—C6b—C7b—C8b	−2.5 (6)
O3a—C6a—C7a—C12a	1.4 (8)	O3b—C6b—C7b—C12b	−1.3 (7)
C5a—C6a—C7a—C12a	−176.9 (5)	C5b—C6b—C7b—C12b	179.3 (4)
C4a—C3a—C8a—C7a	1.2 (6)	C4b—C3b—C8b—C7b	2.2 (6)
C2a—C3a—C8a—C7a	−180.0 (4)	C2b—C3b—C8b—C7b	−176.2 (4)
C4a—C3a—C8a—C9a	179.0 (4)	C4b—C3b—C8b—C9b	−178.5 (4)
C2a—C3a—C8a—C9a	−2.2 (7)	C2b—C3b—C8b—C9b	3.0 (7)
C6a—C7a—C8a—C3a	−0.8 (6)	C6b—C7b—C8b—C3b	−0.3 (6)
C12a—C7a—C8a—C3a	176.3 (4)	C12b—C7b—C8b—C3b	177.8 (4)
C6a—C7a—C8a—C9a	−178.8 (4)	C6b—C7b—C8b—C9b	−179.6 (4)
C12a—C7a—C8a—C9a	−1.7 (6)	C12b—C7b—C8b—C9b	−1.5 (6)
C3a—C8a—C9a—C10a	153.0 (4)	C3b—C8b—C9b—C10b	148.4 (4)
C7a—C8a—C9a—C10a	−29.2 (5)	C7b—C8b—C9b—C10b	−32.4 (6)
C12a—O5a—C10a—C9a	−48.5 (5)	C12b—O5b—C10b—C11b	−169.4 (4)
C12a—O5a—C10a—C11a	−172.8 (4)	C12b—O5b—C10b—C9b	−46.3 (6)
C8a—C9a—C10a—O5a	53.3 (4)	C8b—C9b—C10b—O5b	54.8 (5)
C8a—C9a—C10a—C11a	173.1 (4)	C8b—C9b—C10b—C11b	173.7 (4)
C10a—O5a—C12a—O4a	−163.2 (4)	C10b—O5b—C12b—O4b	−167.1 (4)
C10a—O5a—C12a—C7a	17.5 (6)	C10b—O5b—C12b—C7b	12.7 (7)
C6a—C7a—C12a—O4a	6.8 (7)	C8b—C7b—C12b—O4b	−167.2 (4)
C8a—C7a—C12a—O4a	−170.4 (4)	C6b—C7b—C12b—O4b	11.0 (7)
C6a—C7a—C12a—O5a	−174.0 (4)	C8b—C7b—C12b—O5b	13.0 (7)
C8a—C7a—C12a—O5a	8.8 (6)	C6b—C7b—C12b—O5b	−168.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3a—H3a···O4a	0.82	1.86	2.578 (4)	145
O3b—H3b···O4b	0.82	1.84	2.565 (4)	146