Dimethyl dipropargylmalonate

Geometric parameters of the title compound, C₁₁H₁₂O₄, are in the normal ranges. The crystal packing is stabilized by two weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.078
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C11    -   C12     ..       7.72 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C21    -   C22     ..       7.81 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio

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           30.61
           From the CIF: _reflns_number_total               1609
           Count of symmetry unique reflns         1705
           Completeness (_total/calc)             94.37%
           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
   1 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

Dimethyl dipropargylmalonate

Crystal data

C11H12O4	F(000) = 220
Mr = 208.21	Dx = 1.251 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 8192 reflections
a = 8.260 (1) Å	θ = 4.2–23.5°
b = 9.706 (1) Å	µ = 0.10 mm^−1
c = 7.770 (1) Å	T = 173 K
β = 117.45 (1)°	Plate, colourless
V = 552.80 (11) Å^3	0.37 × 0.35 × 0.28 mm
Z = 2

Data collection

Siemens CCD three-circle diffractometer	1499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 30.6°, θmin = 2.1°
ω scans	h = −11→11
12526 measured reflections	k = −13→13
1609 independent reflections	l = −10→11

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)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.0043P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1609 reflections	Δρmax = 0.17 e Å^−3
139 parameters	Δρmin = −0.14 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (9)

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	0.50860 (17)	0.24343 (11)	0.50908 (18)	0.0219 (2)
C11	0.46245 (16)	0.08962 (12)	0.45346 (17)	0.0233 (2)
H11A	0.5586	0.0481	0.4277	0.028*
H11B	0.4605	0.0396	0.5635	0.028*
C12	0.28507 (18)	0.07423 (13)	0.28125 (18)	0.0266 (2)
C13	0.1408 (2)	0.06339 (16)	0.1400 (2)	0.0366 (3)
H13	0.0262	0.0548	0.0277	0.044*
C21	0.51985 (18)	0.32709 (14)	0.34571 (18)	0.0288 (3)
H21A	0.3985	0.3284	0.2303	0.035*
H21B	0.5543	0.4234	0.3893	0.035*
C22	0.6542 (2)	0.26761 (16)	0.2928 (2)	0.0367 (3)
C23	0.7635 (3)	0.2138 (2)	0.2561 (3)	0.0550 (5)
H23	0.8511	0.1706	0.2268	0.066*
C31	0.36086 (17)	0.30585 (12)	0.55258 (18)	0.0243 (2)
O31	0.25082 (16)	0.39020 (12)	0.45385 (18)	0.0419 (3)
O32	0.36919 (14)	0.24927 (10)	0.71262 (14)	0.0302 (2)
C33	0.2288 (2)	0.29073 (16)	0.7646 (2)	0.0378 (3)
H33A	0.2417	0.3891	0.7966	0.057*
H33B	0.2414	0.2375	0.8773	0.057*
H33C	0.1084	0.2737	0.6552	0.057*
C41	0.69124 (17)	0.25086 (12)	0.69554 (18)	0.0251 (2)
O41	0.78213 (17)	0.15289 (12)	0.77783 (18)	0.0491 (3)
O42	0.73275 (13)	0.38135 (10)	0.75208 (15)	0.0323 (2)
C43	0.8994 (2)	0.40595 (16)	0.9308 (2)	0.0362 (3)
H43A	0.8737	0.3982	1.0416	0.054*
H43B	0.9452	0.4986	0.9278	0.054*
H43C	0.9915	0.3376	0.9434	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0203 (5)	0.0220 (5)	0.0217 (5)	0.0018 (4)	0.0084 (4)	0.0029 (4)
C11	0.0220 (5)	0.0219 (5)	0.0224 (5)	0.0019 (4)	0.0071 (4)	0.0010 (4)
C12	0.0269 (6)	0.0254 (5)	0.0260 (5)	0.0018 (4)	0.0109 (5)	−0.0005 (4)
C13	0.0305 (6)	0.0375 (7)	0.0319 (6)	0.0034 (6)	0.0059 (5)	−0.0027 (6)
C21	0.0303 (6)	0.0297 (6)	0.0275 (6)	0.0010 (5)	0.0144 (5)	0.0067 (5)
C22	0.0454 (8)	0.0365 (7)	0.0361 (7)	−0.0058 (6)	0.0255 (7)	0.0013 (5)
C23	0.0701 (14)	0.0508 (9)	0.0703 (13)	0.0001 (9)	0.0547 (12)	−0.0001 (9)
C31	0.0238 (5)	0.0217 (5)	0.0274 (5)	0.0000 (4)	0.0118 (4)	0.0005 (4)
O31	0.0391 (6)	0.0417 (6)	0.0506 (7)	0.0194 (5)	0.0256 (5)	0.0186 (5)
O32	0.0326 (5)	0.0336 (5)	0.0290 (5)	0.0049 (4)	0.0182 (4)	0.0030 (3)
C33	0.0454 (8)	0.0355 (7)	0.0464 (8)	0.0011 (6)	0.0330 (7)	−0.0035 (6)
C41	0.0212 (5)	0.0268 (5)	0.0251 (5)	−0.0003 (4)	0.0087 (4)	−0.0013 (4)
O41	0.0361 (6)	0.0340 (5)	0.0455 (6)	0.0082 (4)	−0.0083 (5)	−0.0021 (5)
O42	0.0275 (5)	0.0275 (4)	0.0344 (5)	−0.0049 (4)	0.0077 (4)	−0.0031 (4)
C43	0.0268 (6)	0.0381 (7)	0.0380 (7)	−0.0083 (5)	0.0102 (5)	−0.0094 (6)

Geometric parameters (Å, º)

C1—C31	1.5333 (17)	C23—H23	0.9500
C1—C41	1.5378 (17)	C31—O31	1.2008 (16)
C1—C21	1.5453 (16)	C31—O32	1.3318 (16)
C1—C11	1.5521 (16)	O32—C33	1.4499 (16)
C11—C12	1.4669 (17)	C33—H33A	0.9800
C11—H11A	0.9900	C33—H33B	0.9800
C11—H11B	0.9900	C33—H33C	0.9800
C12—C13	1.196 (2)	C41—O41	1.1975 (16)
C13—H13	0.9500	C41—O42	1.3327 (15)
C21—C22	1.468 (2)	O42—C43	1.4551 (17)
C21—H21A	0.9900	C43—H43A	0.9800
C21—H21B	0.9900	C43—H43B	0.9800
C22—C23	1.186 (3)	C43—H43C	0.9800
C31—C1—C41	107.97 (10)	C22—C23—H23	180.0
C31—C1—C21	109.20 (10)	O31—C31—O32	125.15 (12)
C41—C1—C21	110.18 (10)	O31—C31—C1	124.99 (12)
C31—C1—C11	108.85 (10)	O32—C31—C1	109.83 (10)
C41—C1—C11	108.41 (9)	C31—O32—C33	116.24 (11)
C21—C1—C11	112.14 (10)	O32—C33—H33A	109.5
C12—C11—C1	111.46 (10)	O32—C33—H33B	109.5
C12—C11—H11A	109.3	H33A—C33—H33B	109.5
C1—C11—H11A	109.3	O32—C33—H33C	109.5
C12—C11—H11B	109.3	H33A—C33—H33C	109.5
C1—C11—H11B	109.3	H33B—C33—H33C	109.5
H11A—C11—H11B	108.0	O41—C41—O42	125.16 (12)
C13—C12—C11	179.10 (15)	O41—C41—C1	124.55 (11)
C12—C13—H13	180.0	O42—C41—C1	110.29 (10)
C22—C21—C1	111.28 (11)	C41—O42—C43	117.19 (11)
C22—C21—H21A	109.4	O42—C43—H43A	109.5
C1—C21—H21A	109.4	O42—C43—H43B	109.5
C22—C21—H21B	109.4	H43A—C43—H43B	109.5
C1—C21—H21B	109.4	O42—C43—H43C	109.5
H21A—C21—H21B	108.0	H43A—C43—H43C	109.5
C23—C22—C21	176.52 (16)	H43B—C43—H43C	109.5
C31—C1—C11—C12	60.13 (13)	C11—C1—C31—O32	67.14 (13)
C41—C1—C11—C12	177.34 (10)	O31—C31—O32—C33	2.4 (2)
C21—C1—C11—C12	−60.79 (14)	C1—C31—O32—C33	−175.62 (11)
C31—C1—C21—C22	−177.53 (11)	C31—C1—C41—O41	119.67 (16)
C41—C1—C21—C22	64.04 (14)	C21—C1—C41—O41	−121.15 (16)
C11—C1—C21—C22	−56.80 (15)	C11—C1—C41—O41	1.90 (19)
C41—C1—C31—O31	131.65 (14)	C31—C1—C41—O42	−60.07 (12)
C21—C1—C31—O31	11.85 (18)	C21—C1—C41—O42	59.11 (13)
C11—C1—C31—O31	−110.87 (15)	C11—C1—C41—O42	−177.84 (11)
C41—C1—C31—O32	−50.35 (12)	O41—C41—O42—C43	−1.7 (2)
C21—C1—C31—O32	−170.15 (10)	C1—C41—O42—C43	178.01 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O41^i	0.95	2.27	3.1247 (19)	150
C33—H33A···O31^ii	0.98	2.45	3.3969 (19)	162

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