Supra­molecular assembly of diethyl 5-carboxy­benzene-1,3-dicarboxyl­ate

In the crystal structure of the title compound, C₁₃H₁₄O₆, hydrogen-bonded dimers are held together by the cyclic (COOH)₂ synthon. The planar dimers are arranged in layers via additional C—H...O inter­actions. Tight offset-stacking of such layers characterizes the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.055
• wR factor = 0.168
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT391_ALERT_3_C Deviating Methyl C13     H-C-H Bond Angle ......     101.00 Deg.

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

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

diethyl 5-carboxybenzene-1,3-dicarboxylate

Crystal data

C13H14O6	Z = 2
Mr = 266.24	F(000) = 280
Triclinic, P1	Dx = 1.395 Mg m^−3
a = 4.5368 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7315 (4) Å	Cell parameters from 2093 reflections
c = 14.5803 (6) Å	θ = 2.5–30.5°
α = 89.3231 (13)°	µ = 0.11 mm^−1
β = 84.7769 (14)°	T = 110 K
γ = 81.383 (2)°	Block, colorless
V = 633.81 (5) Å^3	0.45 × 0.30 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer	2600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 30.5°, θmin = 2.5°
Detector resolution: 12.8 pixels mm^-1	h = −6→6
1° φ and ω scans	k = −13→13
7439 measured reflections	l = −20→20
3794 independent reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0961P)^2 + 0.0936P] where P = (Fo^2 + 2Fc^2)/3
3794 reflections	(Δ/σ)max = 0.011
228 parameters	Δρmax = 0.46 e Å^−3
1 restraint	Δρmin = −0.34 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	0.5895 (3)	0.70658 (14)	0.36849 (10)	0.0213 (3)
C2	0.7852 (3)	0.69845 (14)	0.28876 (10)	0.0223 (3)
H2	0.903 (4)	0.772 (2)	0.2713 (14)	0.033 (5)*
C3	0.8227 (3)	0.58093 (14)	0.23267 (10)	0.0210 (3)
C4	0.6610 (3)	0.47229 (14)	0.25619 (10)	0.0216 (3)
H4	0.682 (4)	0.3874 (18)	0.2155 (13)	0.025 (4)*
C5	0.4649 (3)	0.48124 (14)	0.33600 (10)	0.0207 (3)
C6	0.4287 (3)	0.59841 (14)	0.39296 (10)	0.0217 (3)
H6	0.291 (4)	0.6074 (19)	0.4496 (15)	0.031 (5)*
C7	0.5546 (3)	0.83427 (15)	0.42626 (11)	0.0238 (3)
C8	1.0358 (3)	0.56587 (14)	0.14808 (10)	0.0219 (3)
C9	0.2852 (3)	0.36824 (14)	0.36296 (10)	0.0221 (3)
C10	1.3433 (4)	0.67885 (17)	0.04106 (11)	0.0296 (4)
H10A	1.236 (4)	0.656 (2)	−0.0125 (15)	0.037 (5)*
H10B	1.522 (4)	0.604 (2)	0.0511 (14)	0.034 (5)*
C11	1.4309 (5)	0.8210 (2)	0.02719 (15)	0.0453 (5)
H11A	1.255 (6)	0.890 (3)	0.0178 (17)	0.056 (7)*
H11B	1.568 (6)	0.826 (3)	−0.0332 (19)	0.059 (7)*
H11C	1.539 (6)	0.845 (3)	0.0830 (19)	0.061 (7)*
C12	0.1456 (4)	0.15601 (16)	0.31680 (12)	0.0279 (3)
H12A	−0.058 (4)	0.1944 (19)	0.3239 (13)	0.027 (4)*
H12B	0.207 (4)	0.103 (2)	0.3726 (15)	0.036 (5)*
C13	0.2099 (6)	0.0618 (2)	0.23426 (16)	0.0520 (6)
H13A	0.117 (6)	0.109 (3)	0.182 (2)	0.064 (8)*
H13B	0.108 (5)	−0.016 (3)	0.2413 (17)	0.056 (7)*
H13C	0.430 (7)	0.023 (3)	0.222 (2)	0.076 (8)*
O14	0.3512 (3)	0.84084 (12)	0.49615 (9)	0.0348 (3)
H14	0.342 (6)	0.9304 (18)	0.527 (2)	0.086 (9)*
O15	0.7063 (3)	0.92769 (11)	0.40736 (8)	0.0311 (3)
O16	1.1373 (2)	0.68510 (11)	0.12477 (7)	0.0264 (3)
O17	1.1085 (2)	0.45820 (11)	0.10536 (8)	0.0279 (3)
O18	0.3250 (2)	0.26729 (11)	0.29900 (8)	0.0270 (3)
O19	0.1206 (3)	0.36816 (11)	0.43254 (8)	0.0307 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0225 (6)	0.0192 (6)	0.0217 (7)	−0.0030 (5)	0.0012 (5)	−0.0047 (5)
C2	0.0225 (7)	0.0198 (6)	0.0244 (8)	−0.0043 (5)	0.0013 (5)	−0.0017 (5)
C3	0.0218 (6)	0.0207 (6)	0.0201 (7)	−0.0041 (5)	0.0022 (5)	−0.0026 (5)
C4	0.0219 (6)	0.0196 (6)	0.0230 (7)	−0.0031 (5)	0.0004 (5)	−0.0030 (5)
C5	0.0205 (6)	0.0194 (6)	0.0218 (7)	−0.0030 (5)	0.0012 (5)	−0.0014 (5)
C6	0.0212 (6)	0.0212 (6)	0.0216 (7)	−0.0018 (5)	0.0017 (5)	−0.0026 (5)
C7	0.0245 (7)	0.0230 (7)	0.0230 (7)	−0.0027 (6)	0.0014 (5)	−0.0037 (5)
C8	0.0222 (6)	0.0220 (6)	0.0219 (7)	−0.0058 (5)	0.0006 (5)	−0.0016 (5)
C9	0.0231 (6)	0.0190 (6)	0.0238 (8)	−0.0038 (5)	0.0011 (5)	−0.0024 (5)
C10	0.0351 (8)	0.0297 (8)	0.0239 (8)	−0.0113 (7)	0.0095 (6)	−0.0046 (6)
C11	0.0573 (12)	0.0338 (9)	0.0440 (12)	−0.0186 (9)	0.0197 (10)	−0.0040 (8)
C12	0.0313 (8)	0.0224 (7)	0.0307 (9)	−0.0111 (6)	0.0053 (6)	−0.0018 (6)
C13	0.0730 (15)	0.0423 (10)	0.0452 (13)	−0.0363 (11)	0.0183 (11)	−0.0165 (9)
O14	0.0373 (6)	0.0310 (6)	0.0351 (7)	−0.0093 (5)	0.0108 (5)	−0.0109 (5)
O15	0.0375 (6)	0.0241 (5)	0.0318 (7)	−0.0109 (5)	0.0079 (5)	−0.0084 (4)
O16	0.0299 (5)	0.0236 (5)	0.0251 (6)	−0.0087 (4)	0.0093 (4)	−0.0050 (4)
O17	0.0327 (6)	0.0247 (5)	0.0257 (6)	−0.0080 (4)	0.0070 (4)	−0.0079 (4)
O18	0.0309 (5)	0.0225 (5)	0.0279 (6)	−0.0106 (4)	0.0067 (4)	−0.0060 (4)
O19	0.0359 (6)	0.0287 (5)	0.0271 (6)	−0.0107 (5)	0.0103 (5)	−0.0036 (4)

Geometric parameters (Å, º)

C1—C2	1.392 (2)	C9—O18	1.3435 (17)
C1—C6	1.3934 (19)	C10—O16	1.4643 (18)
C1—C7	1.4900 (19)	C10—C11	1.502 (2)
C2—C3	1.3945 (19)	C10—H10A	1.00 (2)
C2—H2	0.973 (19)	C10—H10B	1.03 (2)
C3—C4	1.3969 (19)	C11—H11A	0.98 (3)
C3—C8	1.491 (2)	C11—H11B	1.04 (3)
C4—C5	1.394 (2)	C11—H11C	1.03 (3)
C4—H4	1.011 (18)	C12—O18	1.4565 (17)
C5—C6	1.3993 (19)	C12—C13	1.502 (2)
C5—C9	1.4926 (19)	C12—H12A	0.940 (19)
C6—H6	0.99 (2)	C12—H12B	0.99 (2)
C7—O15	1.2342 (18)	C13—H13A	0.99 (3)
C7—O14	1.3064 (18)	C13—H13B	0.95 (2)
C8—O17	1.2121 (17)	C13—H13C	1.01 (3)
C8—O16	1.3401 (17)	O14—H14	0.976 (10)
C9—O19	1.2038 (17)
C2—C1—C6	120.69 (13)	O16—C10—C11	107.01 (13)
C2—C1—C7	118.30 (12)	O16—C10—H10A	109.0 (11)
C6—C1—C7	121.01 (13)	C11—C10—H10A	108.9 (12)
C1—C2—C3	119.99 (13)	O16—C10—H10B	107.3 (11)
C1—C2—H2	121.9 (11)	C11—C10—H10B	112.8 (10)
C3—C2—H2	118.1 (11)	H10A—C10—H10B	111.7 (16)
C2—C3—C4	119.79 (13)	C10—C11—H11A	110.6 (14)
C2—C3—C8	121.91 (12)	C10—C11—H11B	111.5 (14)
C4—C3—C8	118.29 (12)	H11A—C11—H11B	103 (2)
C5—C4—C3	119.92 (13)	C10—C11—H11C	108.9 (14)
C5—C4—H4	119.3 (10)	H11A—C11—H11C	112 (2)
C3—C4—H4	120.8 (10)	H11B—C11—H11C	110.2 (19)
C4—C5—C6	120.47 (12)	O18—C12—C13	106.35 (13)
C4—C5—C9	121.58 (12)	O18—C12—H12A	109.1 (11)
C6—C5—C9	117.95 (12)	C13—C12—H12A	110.5 (11)
C1—C6—C5	119.13 (13)	O18—C12—H12B	109.8 (11)
C1—C6—H6	118.9 (11)	C13—C12—H12B	109.5 (11)
C5—C6—H6	122.0 (11)	H12A—C12—H12B	111.3 (16)
O15—C7—O14	123.04 (13)	C12—C13—H13A	109.0 (16)
O15—C7—C1	121.37 (13)	C12—C13—H13B	112.0 (15)
O14—C7—C1	115.58 (12)	H13A—C13—H13B	101 (2)
O17—C8—O16	123.98 (13)	C12—C13—H13C	112.9 (17)
O17—C8—C3	123.84 (13)	H13A—C13—H13C	115 (2)
O16—C8—C3	112.18 (12)	H13B—C13—H13C	106 (2)
O19—C9—O18	123.89 (12)	C7—O14—H14	108.1 (18)
O19—C9—C5	124.44 (12)	C8—O16—C10	115.22 (11)
O18—C9—C5	111.66 (12)	C9—O18—C12	115.67 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O15^i	0.98 (1)	1.67 (1)	2.637 (2)	171 (3)
C6—H6···O19^ii	0.99 (2)	2.40 (2)	3.378 (2)	169 (2)

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