6-Acetoxy­meth­yl-2-(2-methoxy­phen­oxy)tetra­hydro­pyran-3,4,5-tri­yl triacetate

The mol­ecule of the title compound, C₂₁H₂₆O₁₁, possesses normal geometric parameters. Inter­molecular C—H...O hydrogen bonds link adjacent mol­ecules to form one-dimensional chains along the crystallographic a axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.118
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.83 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H3     ..  H102    ..       1.88 Ang.

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               2893
           Count of symmetry unique reflns         3053
           Completeness (_total/calc)             94.76%
           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

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

6-Acetoxymethyl-2-(2-methoxyphenoxy)tetrahydropyran-3,4,5-triyl triacetate

Crystal data

C21H26O11	F(000) = 960.00
Mr = 454.43	Dx = 1.295 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7872 reflections
a = 8.1321 (2) Å	θ = 2.0–27.5°
b = 10.6922 (3) Å	µ = 0.11 mm^−1
c = 26.8033 (7) Å	T = 295 K
V = 2330.5 (1) Å^3	Block, colorless
Z = 4	0.45 × 0.40 × 0.35 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2377 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.032
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.928, Tmax = 0.964	k = −13→12
16634 measured reflections	l = −34→34
2893 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0019Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.040	(Δ/σ)max < 0.001
wR(F^2) = 0.118	Δρmax = 0.26 e Å^−3
S = 1.01	Δρmin = −0.21 e Å^−3
2893 reflections	Extinction correction: Larson (1970), equation 22
290 parameters	Extinction coefficient: 399 (72)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.5386 (3)	0.8350 (3)	0.7420 (1)	0.1037 (9)
O2	0.6600 (2)	0.6808 (1)	0.67707 (6)	0.0473 (4)
O3	0.4663 (2)	0.7336 (1)	0.59538 (6)	0.0472 (4)
O4	0.2445 (3)	0.6422 (3)	0.6270 (1)	0.1039 (9)
O5	0.4567 (2)	0.5347 (1)	0.52252 (6)	0.0455 (4)
O6	0.4419 (3)	0.7096 (2)	0.47634 (8)	0.0722 (6)
O7	0.7872 (2)	0.4399 (1)	0.50265 (5)	0.0445 (4)
O8	0.6928 (4)	0.2428 (2)	0.50296 (9)	0.0820 (7)
O10	0.8451 (3)	0.2840 (2)	0.62339 (7)	0.0604 (5)
O11	1.0031 (5)	0.1240 (3)	0.6065 (2)	0.163 (2)
O12	0.7980 (2)	0.5305 (1)	0.63402 (5)	0.0426 (4)
C1	0.4708 (6)	0.9230 (7)	0.7753 (3)	0.086 (1)
C2	0.7053 (4)	0.8273 (3)	0.7414 (1)	0.0614 (8)
C3	0.8102 (5)	0.8958 (3)	0.7717 (1)	0.0722 (9)
C4	0.9769 (5)	0.8831 (4)	0.7669 (1)	0.074 (1)
C5	1.0422 (4)	0.8021 (4)	0.7326 (1)	0.073 (1)
C6	0.9390 (3)	0.7324 (3)	0.7020 (1)	0.0584 (7)
C7	0.7712 (3)	0.7459 (2)	0.70623 (8)	0.0463 (6)
C8	0.7111 (3)	0.6440 (2)	0.62958 (8)	0.0401 (5)
C9	0.5581 (3)	0.6203 (2)	0.59916 (8)	0.0399 (5)
C10	0.6043 (3)	0.5755 (2)	0.54718 (8)	0.0381 (5)
C11	0.7168 (3)	0.4630 (2)	0.55115 (8)	0.0391 (5)
C12	0.8588 (3)	0.4861 (2)	0.58709 (8)	0.0413 (5)
C13	0.3109 (4)	0.7337 (3)	0.6126 (1)	0.0610 (8)
C14	0.2397 (5)	0.8618 (3)	0.6106 (1)	0.084 (1)
C15	0.3841 (3)	0.6127 (2)	0.48937 (9)	0.0497 (6)
C16	0.2228 (4)	0.5615 (3)	0.4736 (1)	0.0691 (9)
C17	0.7690 (3)	0.3238 (2)	0.48297 (9)	0.0504 (6)
C18	0.8566 (4)	0.3112 (3)	0.4350 (1)	0.0653 (8)
C19	0.9542 (3)	0.3683 (2)	0.59830 (9)	0.0515 (6)
C20	0.8868 (5)	0.1651 (3)	0.6276 (1)	0.080 (1)
C21	0.7711 (7)	0.0920 (3)	0.6575 (2)	0.114 (2)
H3	0.7653	0.9541	0.7964	0.087*
H4	1.0505	0.9321	0.7882	0.089*
H5	1.1617	0.7930	0.7296	0.088*
H6	0.9855	0.6737	0.6777	0.070*
H8	0.7795	0.7086	0.6141	0.048*
H9	0.4912	0.5564	0.6158	0.048*
H10	0.6575	0.6428	0.5283	0.045*
H11	0.6538	0.3898	0.5620	0.047*
H12	0.9329	0.5488	0.5728	0.050*
H192	1.0480	0.3872	0.6193	0.061*
H191	0.9920	0.3307	0.5674	0.062*
H142	0.2613	0.9041	0.6415	0.101*
H143	0.1232	0.8572	0.6053	0.101*
H141	0.2899	0.9072	0.5837	0.101*
H162	0.1966	0.5928	0.4410	0.083*
H163	0.2286	0.4719	0.4727	0.083*
H161	0.1393	0.5868	0.4968	0.083*
H181	0.7841	0.3338	0.4082	0.078*
H182	0.8921	0.2263	0.4308	0.079*
H183	0.9503	0.3659	0.4349	0.079*
H211	0.8033	0.0953	0.6919	0.137*
H212	0.7696	0.0065	0.6465	0.137*
H213	0.6634	0.1276	0.6538	0.137*
H103	0.4517	0.8818	0.8066	0.103*
H101	0.3686	0.9543	0.7624	0.103*
H102	0.5457	0.9913	0.7802	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.066 (1)	0.072 (1)	0.174 (3)	0.012 (1)	0.053 (2)	0.0034 (7)
O2	0.0502 (9)	0.0470 (8)	0.0447 (8)	−0.0044 (8)	0.0071 (7)	−0.0107 (7)
O3	0.0489 (9)	0.0367 (7)	0.0561 (9)	0.0052 (7)	0.0075 (8)	0.0034 (7)
O4	0.066 (1)	0.072 (1)	0.174 (3)	0.012 (1)	0.053 (2)	0.023 (2)
O5	0.0493 (9)	0.0356 (7)	0.0515 (9)	−0.0017 (7)	−0.0093 (7)	0.0041 (7)
O6	0.079 (1)	0.054 (1)	0.083 (1)	−0.007 (1)	−0.022 (1)	0.025 (1)
O7	0.0548 (9)	0.0409 (8)	0.0378 (7)	−0.0010 (7)	0.0063 (7)	−0.0051 (6)
O8	0.122 (2)	0.0439 (9)	0.080 (1)	−0.016 (1)	0.013 (1)	−0.0144 (9)
O10	0.078 (1)	0.0458 (8)	0.057 (1)	0.0143 (9)	0.004 (1)	0.0093 (8)
O11	0.136 (3)	0.066 (2)	0.286 (5)	0.042 (2)	0.072 (4)	0.028 (2)
O12	0.0511 (9)	0.0408 (8)	0.0359 (7)	0.0066 (7)	0.0004 (7)	−0.0014 (6)
C1	0.083 (2)	0.074 (2)	0.108 (2)	0.037 (2)	0.016 (2)	0.011 (2)
C2	0.064 (2)	0.064 (2)	0.055 (1)	−0.006 (1)	0.011 (1)	−0.018 (1)
C3	0.087 (2)	0.074 (2)	0.056 (2)	−0.005 (2)	0.001 (2)	−0.028 (1)
C4	0.082 (2)	0.086 (2)	0.055 (2)	−0.015 (2)	−0.015 (2)	−0.013 (2)
C5	0.060 (2)	0.094 (2)	0.066 (2)	−0.004 (2)	−0.013 (1)	−0.016 (2)
C6	0.059 (2)	0.060 (2)	0.056 (1)	0.001 (1)	−0.005 (1)	−0.008 (1)
C7	0.057 (1)	0.043 (1)	0.039 (1)	−0.005 (1)	0.001 (1)	−0.0032 (9)
C8	0.046 (1)	0.036 (1)	0.039 (1)	0.001 (1)	0.004 (1)	−0.0018 (8)
C9	0.042 (1)	0.0326 (9)	0.045 (1)	0.0024 (9)	0.003 (1)	0.0013 (9)
C10	0.040 (1)	0.0334 (9)	0.040 (1)	−0.0017 (9)	−0.0014 (9)	0.0010 (9)
C11	0.045 (1)	0.0333 (9)	0.039 (1)	0.001 (1)	0.0057 (9)	0.0007 (8)
C12	0.046 (1)	0.040 (1)	0.038 (1)	0.002 (1)	0.0044 (9)	−0.0012 (9)
C13	0.057 (2)	0.055 (1)	0.071 (2)	0.013 (1)	0.014 (1)	0.002 (1)
C14	0.083 (2)	0.070 (2)	0.098 (2)	0.037 (2)	0.016 (2)	0.008 (2)
C15	0.058 (1)	0.039 (1)	0.052 (1)	0.008 (1)	−0.010 (1)	0.001 (1)
C16	0.065 (2)	0.057 (2)	0.085 (2)	0.006 (1)	−0.028 (2)	0.001 (1)
C17	0.057 (1)	0.043 (1)	0.051 (1)	0.008 (1)	−0.008 (1)	−0.011 (1)
C18	0.073 (2)	0.069 (2)	0.054 (1)	0.013 (2)	−0.001 (1)	−0.018 (1)
C19	0.051 (1)	0.055 (1)	0.048 (1)	0.013 (1)	−0.000 (1)	0.001 (1)
C20	0.094 (2)	0.050 (1)	0.096 (2)	0.013 (2)	0.004 (2)	0.010 (2)
C21	0.164 (5)	0.063 (2)	0.115 (3)	−0.005 (3)	0.003 (3)	0.030 (2)

Geometric parameters (Å, º)

O1—C1	1.410 (8)	C15—C16	1.482 (4)
O1—C2	1.358 (4)	C17—C18	1.476 (4)
O2—C7	1.383 (3)	C20—C21	1.464 (6)
O2—C8	1.396 (3)	C1—H103	0.9600
O3—C9	1.427 (3)	C1—H101	0.9600
O3—C13	1.345 (3)	C1—H102	0.9600
O4—C13	1.183 (4)	C3—H3	0.9800
O5—C10	1.438 (3)	C4—H4	0.9800
O5—C15	1.354 (3)	C5—H5	0.9800
O6—C15	1.190 (3)	C6—H6	0.9800
O7—C11	1.442 (3)	C8—H8	0.9800
O7—C17	1.356 (3)	C9—H9	0.9800
O8—C17	1.192 (4)	C10—H10	0.9800
O10—C19	1.432 (3)	C11—H11	0.9800
O10—C20	1.320 (4)	C12—H12	0.9800
O11—C20	1.187 (6)	C14—H142	0.9600
O12—C8	1.409 (3)	C14—H143	0.9600
O12—C12	1.433 (3)	C14—H141	0.9600
C2—C3	1.388 (5)	C16—H162	0.9600
C2—C7	1.390 (4)	C16—H163	0.9600
C3—C4	1.368 (5)	C16—H161	0.9600
C4—C5	1.370 (5)	C18—H181	0.9600
C5—C6	1.389 (4)	C18—H182	0.9600
C6—C7	1.377 (4)	C18—H183	0.9600
C8—C9	1.509 (3)	C19—H192	0.9700
C9—C10	1.520 (3)	C19—H191	0.9700
C10—C11	1.515 (3)	C21—H211	0.9600
C11—C12	1.524 (3)	C21—H212	0.9599
C12—C19	1.509 (3)	C21—H213	0.9600
C13—C14	1.488 (4)
C2—O1—C1	116.0 (3)	O10—C19—H191	109.5960
O1—C2—C3	125.1 (3)	O10—C19—H192	110.1829
O1—C2—C7	115.6 (3)	O12—C8—H8	110.9861
O2—C7—C2	116.4 (2)	O12—C12—H12	109.1830
O2—C7—C6	123.3 (2)	H101—C1—H103	109.4756
C8—O2—C7	117.6 (2)	H102—C1—H103	109.4826
O2—C8—O12	108.4 (2)	H102—C1—H101	109.4693
O2—C8—C9	107.2 (2)	C2—C3—H3	120.2033
O3—C9—C8	109.1 (2)	H3—C3—C4	119.7258
C13—O3—C9	117.9 (2)	C3—C4—H4	119.7873
O3—C9—C10	109.4 (2)	H4—C4—C5	119.5120
O3—C13—O4	122.7 (3)	C4—C5—H5	120.1247
O3—C13—C14	110.7 (2)	C5—C6—H6	120.1350
O4—C13—C14	126.6 (3)	H5—C5—C6	119.8383
O5—C10—C9	108.1 (2)	H6—C6—C7	120.2611
C15—O5—C10	118.6 (2)	H8—C8—C9	110.9254
O5—C10—C11	107.2 (2)	C8—C9—H9	109.2415
O5—C15—O6	123.8 (2)	H9—C9—C10	109.5194
O5—C15—C16	110.2 (2)	C9—C10—H10	110.6119
O6—C15—C16	126.0 (3)	H10—C10—C11	110.6405
O7—C11—C12	107.3 (2)	C10—C11—H11	109.8502
O7—C11—C10	108.2 (2)	H11—C11—C12	109.7424
C17—O7—C11	117.7 (2)	C11—C12—H12	109.2333
O7—C17—O8	123.2 (2)	H12—C12—C19	109.4479
O7—C17—C18	111.7 (2)	C12—C19—H191	109.8243
O8—C17—C18	125.2 (3)	C12—C19—H192	110.2752
O10—C19—C12	107.5 (2)	C13—C14—H142	109.3691
C20—O10—C19	119.1 (3)	C13—C14—H143	109.9649
O10—C20—O11	121.4 (4)	C13—C14—H141	109.0644
O10—C20—C21	113.3 (3)	H143—C14—H142	109.5157
O11—C20—C21	125.1 (3)	H141—C14—H142	109.4743
O12—C8—C9	108.3 (2)	H141—C14—H143	109.4375
C12—O12—C8	112.6 (2)	C15—C16—H162	109.1449
O12—C12—C11	110.3 (2)	C15—C16—H163	109.4692
O12—C12—C19	106.2 (2)	C15—C16—H161	109.7731
C7—C2—C3	119.4 (3)	H163—C16—H162	109.4693
C2—C3—C4	120.1 (3)	H161—C16—H162	109.5574
C2—C7—C6	120.2 (2)	H161—C16—H163	109.4130
C3—C4—C5	120.7 (3)	C17—C18—H181	109.3916
C4—C5—C6	120.0 (3)	C17—C18—H182	109.5560
C5—C6—C7	119.6 (3)	C17—C18—H183	109.2224
C8—C9—C10	110.1 (2)	H182—C18—H181	109.4987
C9—C10—C11	109.6 (2)	H183—C18—H181	109.4716
C10—C11—C12	111.9 (2)	H183—C18—H182	109.6863
C11—C12—C19	112.4 (2)	H191—C19—H192	109.4591
O1—C1—H103	108.0868	C20—C21—H211	109.3769
O1—C1—H101	110.0289	C20—C21—H212	110.4017
O1—C1—H102	110.2752	C20—C21—H213	108.5018
O2—C8—H8	110.9053	H212—C21—H211	109.4843
O3—C9—H9	109.4624	H213—C21—H211	109.4659
O5—C10—H10	110.6564	H213—C21—H212	109.5909
O7—C11—H11	109.7462
C1—O1—C2—C3	2.0 (5)	O1—C2—C7—C6	179.1 (3)
C8—O2—C7—C2	152.4 (2)	C2—C3—C4—C5	−0.8 (5)
C8—O2—C7—C6	−28.1 (3)	C3—C4—C5—C6	0.5 (5)
C7—O2—C8—O12	83.9 (2)	C4—C5—C6—C7	0.3 (5)
C13—O3—C9—C8	−121.5 (2)	C5—C6—C7—O2	179.6 (2)
C9—O3—C13—O4	−5.8 (4)	C5—C6—C7—C2	−1.0 (4)
C15—O5—C10—C9	100.4 (2)	O2—C8—C9—O3	61.8 (2)
C10—O5—C15—O6	6.1 (3)	O12—C8—C9—O3	178.5 (2)
C17—O7—C11—C10	−125.4 (2)	O3—C9—C10—O5	−69.4 (2)
C11—O7—C17—O8	2.9 (4)	C8—C9—C10—O5	170.7 (2)
C20—O10—C19—C12	165.3 (2)	O5—C10—C11—O7	75.5 (2)
C19—O10—C20—O11	−8.2 (6)	C9—C10—C11—O7	−167.5 (2)
C12—O12—C8—O2	−178.8 (2)	O7—C11—C12—O12	170.2 (2)
C8—O12—C12—C11	−60.4 (2)	C10—C11—C12—O12	51.7 (2)
O1—C2—C3—C4	−178.1 (3)	O12—C12—C19—O10	56.8 (2)
O1—C2—C7—O2	−1.4 (4)	C11—C12—C19—O10	−63.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4^i	0.98	2.53	3.338 (4)	140
C16—H163···O8^ii	0.96	2.40	3.323 (4)	160
C18—H181···O11^ii	0.96	2.36	3.159 (5)	140

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