3-(2-Methoxy­phen­oxy)propane-1,2-diol

The title compound, C₁₀H₁₄O₄, is used to cure coughs and clear up phlegm and it is also used as an inter­mediate in the synthesis of other medicinal products. The entire molecule, except for atoms C10 and O4, is essentially planar (to within 0.001 Å).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.148
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               2248
           Count of symmetry unique reflns         1351
           Completeness (_total/calc)            166.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       897
           Fraction of Friedel pairs measured     0.664
           Are heavy atom types Z>Si present         no

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

   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-(2-Methoxyphenoxy)propane-1,2-diol

Crystal data

C10H14O4	Dx = 1.343 Mg m^−3
Mr = 198.21	Melting point: 355.4 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 4.9836 (10) Å	Cell parameters from 9631 reflections
b = 7.6562 (15) Å	θ = 3.1–27.5°
c = 25.698 (5) Å	µ = 0.10 mm^−1
V = 980.5 (3) Å^3	T = 293 K
Z = 4	Needle, colorless
F(000) = 424	0.38 × 0.20 × 0.09 mm

Data collection

Rigaku R-axis Rapid IP area-detector diffractometer	2248 independent reflections
Radiation source: rotating anode	1862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
Oscillation scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.962, Tmax = 0.991	k = −9→9
9593 measured reflections	l = −33→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0903P)^2 + 0.0695P] where P = (Fo^2 + 2Fc^2)/3
2248 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.2993 (5)	0.5757 (4)	0.02231 (11)	0.0575 (7)
H1A	1.2735	0.6945	0.0115	0.086*
H1B	1.3004	0.5009	−0.0077	0.086*
H1C	1.4674	0.5655	0.0403	0.086*
C2	1.0968 (4)	0.3583 (3)	0.07477 (8)	0.0361 (4)
C3	1.2737 (5)	0.2306 (3)	0.05803 (8)	0.0450 (5)
H3A	1.3976	0.2562	0.0321	0.054*
C4	1.2676 (5)	0.0650 (3)	0.07965 (10)	0.0497 (6)
H4A	1.3853	−0.0203	0.0677	0.060*
C5	1.0883 (5)	0.0258 (3)	0.11871 (11)	0.0483 (6)
H5A	1.0859	−0.0855	0.1332	0.058*
C6	0.9106 (5)	0.1529 (3)	0.13648 (9)	0.0409 (5)
H6A	0.7896	0.1264	0.1629	0.049*
C7	0.9138 (4)	0.3183 (3)	0.11489 (7)	0.0339 (4)
C8	0.5792 (4)	0.4210 (3)	0.17351 (8)	0.0348 (4)
H8A	0.6862	0.3980	0.2043	0.042*
H8B	0.4656	0.3204	0.1670	0.042*
C9	0.4095 (4)	0.5827 (3)	0.18138 (7)	0.0319 (4)
H9A	0.2902	0.5954	0.1513	0.038*
C10	0.5733 (4)	0.7480 (3)	0.18666 (9)	0.0395 (5)
H10A	0.6559	0.7752	0.1535	0.047*
H10B	0.4554	0.8441	0.1958	0.047*
O1	1.0869 (3)	0.5255 (2)	0.05609 (6)	0.0469 (4)
O2	0.7492 (3)	0.45292 (19)	0.12978 (6)	0.0394 (4)
O3	0.2484 (3)	0.5507 (2)	0.22650 (6)	0.0406 (4)
H3B	0.2657	0.4485	0.2355	0.061*
O4	0.7766 (3)	0.7314 (2)	0.22526 (7)	0.0499 (4)
H4C	0.8962	0.6676	0.2144	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0508 (13)	0.0691 (19)	0.0527 (14)	−0.0041 (13)	0.0085 (11)	0.0197 (13)
C2	0.0337 (10)	0.0410 (11)	0.0336 (9)	−0.0013 (9)	−0.0008 (9)	−0.0026 (8)
C3	0.0392 (11)	0.0528 (14)	0.0432 (12)	0.0021 (11)	0.0050 (10)	−0.0095 (10)
C4	0.0380 (11)	0.0470 (14)	0.0643 (15)	0.0119 (11)	0.0007 (12)	−0.0128 (11)
C5	0.0398 (11)	0.0368 (12)	0.0684 (14)	0.0045 (10)	−0.0046 (12)	0.0005 (10)
C6	0.0340 (9)	0.0383 (12)	0.0505 (12)	−0.0002 (10)	0.0023 (10)	−0.0011 (9)
C7	0.0298 (9)	0.0358 (11)	0.0362 (10)	0.0009 (8)	−0.0018 (8)	−0.0044 (8)
C8	0.0313 (9)	0.0362 (11)	0.0370 (10)	0.0012 (9)	0.0029 (8)	−0.0020 (8)
C9	0.0295 (9)	0.0328 (10)	0.0335 (9)	0.0028 (8)	−0.0010 (8)	0.0016 (8)
C10	0.0348 (9)	0.0357 (11)	0.0480 (11)	0.0010 (10)	−0.0002 (10)	0.0009 (9)
O1	0.0460 (8)	0.0486 (10)	0.0462 (8)	0.0021 (8)	0.0115 (8)	0.0087 (7)
O2	0.0408 (7)	0.0353 (8)	0.0420 (8)	0.0051 (7)	0.0102 (7)	0.0022 (6)
O3	0.0369 (7)	0.0400 (9)	0.0450 (8)	0.0080 (7)	0.0089 (7)	0.0098 (6)
O4	0.0340 (7)	0.0476 (10)	0.0682 (10)	0.0102 (7)	−0.0105 (7)	−0.0186 (8)

Geometric parameters (Å, º)

C1—O1	1.422 (3)	C6—H6A	0.9300
C1—H1A	0.9600	C7—O2	1.372 (2)
C1—H1B	0.9600	C8—O2	1.428 (2)
C1—H1C	0.9600	C8—C9	1.513 (3)
C2—O1	1.368 (3)	C8—H8A	0.9700
C2—C3	1.385 (3)	C8—H8B	0.9700
C2—C7	1.410 (3)	C9—O3	1.431 (2)
C3—C4	1.384 (4)	C9—C10	1.512 (3)
C3—H3A	0.9300	C9—H9A	0.9800
C4—C5	1.377 (4)	C10—O4	1.424 (3)
C4—H4A	0.9300	C10—H10A	0.9700
C5—C6	1.393 (3)	C10—H10B	0.9700
C5—H5A	0.9300	O3—H3B	0.8200
C6—C7	1.383 (3)	O4—H4C	0.8200
O1—C1—H1A	109.5	C6—C7—C2	120.0 (2)
O1—C1—H1B	109.5	O2—C8—C9	107.24 (16)
H1A—C1—H1B	109.5	O2—C8—H8A	110.3
O1—C1—H1C	109.5	C9—C8—H8A	110.3
H1A—C1—H1C	109.5	O2—C8—H8B	110.3
H1B—C1—H1C	109.5	C9—C8—H8B	110.3
O1—C2—C3	125.1 (2)	H8A—C8—H8B	108.5
O1—C2—C7	115.88 (18)	O3—C9—C10	111.92 (16)
C3—C2—C7	119.0 (2)	O3—C9—C8	106.34 (15)
C4—C3—C2	120.5 (2)	C10—C9—C8	113.31 (16)
C4—C3—H3A	119.7	O3—C9—H9A	108.4
C2—C3—H3A	119.7	C10—C9—H9A	108.4
C5—C4—C3	120.4 (2)	C8—C9—H9A	108.4
C5—C4—H4A	119.8	O4—C10—C9	111.82 (18)
C3—C4—H4A	119.8	O4—C10—H10A	109.3
C4—C5—C6	120.0 (2)	C9—C10—H10A	109.3
C4—C5—H5A	120.0	O4—C10—H10B	109.3
C6—C5—H5A	120.0	C9—C10—H10B	109.3
C7—C6—C5	120.1 (2)	H10A—C10—H10B	107.9
C7—C6—H6A	120.0	C2—O1—C1	116.11 (19)
C5—C6—H6A	120.0	C7—O2—C8	116.46 (16)
O2—C7—C6	124.70 (19)	C9—O3—H3B	109.5
O2—C7—C2	115.32 (18)	C10—O4—H4C	109.5
O1—C2—C3—C4	179.8 (2)	C3—C2—C7—C6	−0.8 (3)
C7—C2—C3—C4	1.2 (3)	O2—C8—C9—O3	−177.81 (14)
C2—C3—C4—C5	−1.0 (4)	O2—C8—C9—C10	−54.4 (2)
C3—C4—C5—C6	0.4 (4)	O3—C9—C10—O4	68.2 (2)
C4—C5—C6—C7	0.1 (4)	C8—C9—C10—O4	−52.0 (2)
C5—C6—C7—O2	−179.5 (2)	C3—C2—O1—C1	−9.1 (3)
C5—C6—C7—C2	0.1 (3)	C7—C2—O1—C1	169.5 (2)
O1—C2—C7—O2	0.2 (3)	C6—C7—O2—C8	5.2 (3)
C3—C2—C7—O2	178.88 (18)	C2—C7—O2—C8	−174.42 (16)
O1—C2—C7—C6	−179.51 (19)	C9—C8—O2—C7	−177.72 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4^i	0.82	1.96	2.744 (2)	161
O4—H4C···O3^ii	0.82	1.99	2.729 (2)	149

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