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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050409/cs2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050409/cs2023Isup2.hkl
Contains datablock I

CCDC reference: 629635

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

Computing details top

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 top
Crystal data top
C13H14O6Z = 2
Mr = 266.24F(000) = 280
Triclinic, P1Dx = 1.395 Mg m3
a = 4.5368 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7315 (4) ÅCell parameters from 2093 reflections
c = 14.5803 (6) Åθ = 2.5–30.5°
α = 89.3231 (13)°µ = 0.11 mm1
β = 84.7769 (14)°T = 110 K
γ = 81.383 (2)°Block, colorless
V = 633.81 (5) Å30.45 × 0.30 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer
2600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 30.5°, θmin = 2.5°
Detector resolution: 12.8 pixels mm-1h = 66
φ and ω scansk = 1313
7439 measured reflectionsl = 2020
3794 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0961P)2 + 0.0936P]
where P = (Fo2 + 2Fc2)/3
3794 reflections(Δ/σ)max = 0.011
228 parametersΔρmax = 0.46 e Å3
1 restraintΔρmin = 0.34 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.5895 (3)0.70658 (14)0.36849 (10)0.0213 (3)
C20.7852 (3)0.69845 (14)0.28876 (10)0.0223 (3)
H20.903 (4)0.772 (2)0.2713 (14)0.033 (5)*
C30.8227 (3)0.58093 (14)0.23267 (10)0.0210 (3)
C40.6610 (3)0.47229 (14)0.25619 (10)0.0216 (3)
H40.682 (4)0.3874 (18)0.2155 (13)0.025 (4)*
C50.4649 (3)0.48124 (14)0.33600 (10)0.0207 (3)
C60.4287 (3)0.59841 (14)0.39296 (10)0.0217 (3)
H60.291 (4)0.6074 (19)0.4496 (15)0.031 (5)*
C70.5546 (3)0.83427 (15)0.42626 (11)0.0238 (3)
C81.0358 (3)0.56587 (14)0.14808 (10)0.0219 (3)
C90.2852 (3)0.36824 (14)0.36296 (10)0.0221 (3)
C101.3433 (4)0.67885 (17)0.04106 (11)0.0296 (4)
H10A1.236 (4)0.656 (2)0.0125 (15)0.037 (5)*
H10B1.522 (4)0.604 (2)0.0511 (14)0.034 (5)*
C111.4309 (5)0.8210 (2)0.02719 (15)0.0453 (5)
H11A1.255 (6)0.890 (3)0.0178 (17)0.056 (7)*
H11B1.568 (6)0.826 (3)0.0332 (19)0.059 (7)*
H11C1.539 (6)0.845 (3)0.0830 (19)0.061 (7)*
C120.1456 (4)0.15601 (16)0.31680 (12)0.0279 (3)
H12A0.058 (4)0.1944 (19)0.3239 (13)0.027 (4)*
H12B0.207 (4)0.103 (2)0.3726 (15)0.036 (5)*
C130.2099 (6)0.0618 (2)0.23426 (16)0.0520 (6)
H13A0.117 (6)0.109 (3)0.182 (2)0.064 (8)*
H13B0.108 (5)0.016 (3)0.2413 (17)0.056 (7)*
H13C0.430 (7)0.023 (3)0.222 (2)0.076 (8)*
O140.3512 (3)0.84084 (12)0.49615 (9)0.0348 (3)
H140.342 (6)0.9304 (18)0.527 (2)0.086 (9)*
O150.7063 (3)0.92769 (11)0.40736 (8)0.0311 (3)
O161.1373 (2)0.68510 (11)0.12477 (7)0.0264 (3)
O171.1085 (2)0.45820 (11)0.10536 (8)0.0279 (3)
O180.3250 (2)0.26729 (11)0.29900 (8)0.0270 (3)
O190.1206 (3)0.36816 (11)0.43254 (8)0.0307 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0225 (6)0.0192 (6)0.0217 (7)0.0030 (5)0.0012 (5)0.0047 (5)
C20.0225 (7)0.0198 (6)0.0244 (8)0.0043 (5)0.0013 (5)0.0017 (5)
C30.0218 (6)0.0207 (6)0.0201 (7)0.0041 (5)0.0022 (5)0.0026 (5)
C40.0219 (6)0.0196 (6)0.0230 (7)0.0031 (5)0.0004 (5)0.0030 (5)
C50.0205 (6)0.0194 (6)0.0218 (7)0.0030 (5)0.0012 (5)0.0014 (5)
C60.0212 (6)0.0212 (6)0.0216 (7)0.0018 (5)0.0017 (5)0.0026 (5)
C70.0245 (7)0.0230 (7)0.0230 (7)0.0027 (6)0.0014 (5)0.0037 (5)
C80.0222 (6)0.0220 (6)0.0219 (7)0.0058 (5)0.0006 (5)0.0016 (5)
C90.0231 (6)0.0190 (6)0.0238 (8)0.0038 (5)0.0011 (5)0.0024 (5)
C100.0351 (8)0.0297 (8)0.0239 (8)0.0113 (7)0.0095 (6)0.0046 (6)
C110.0573 (12)0.0338 (9)0.0440 (12)0.0186 (9)0.0197 (10)0.0040 (8)
C120.0313 (8)0.0224 (7)0.0307 (9)0.0111 (6)0.0053 (6)0.0018 (6)
C130.0730 (15)0.0423 (10)0.0452 (13)0.0363 (11)0.0183 (11)0.0165 (9)
O140.0373 (6)0.0310 (6)0.0351 (7)0.0093 (5)0.0108 (5)0.0109 (5)
O150.0375 (6)0.0241 (5)0.0318 (7)0.0109 (5)0.0079 (5)0.0084 (4)
O160.0299 (5)0.0236 (5)0.0251 (6)0.0087 (4)0.0093 (4)0.0050 (4)
O170.0327 (6)0.0247 (5)0.0257 (6)0.0080 (4)0.0070 (4)0.0079 (4)
O180.0309 (5)0.0225 (5)0.0279 (6)0.0106 (4)0.0067 (4)0.0060 (4)
O190.0359 (6)0.0287 (5)0.0271 (6)0.0107 (5)0.0103 (5)0.0036 (4)
Geometric parameters (Å, º) top
C1—C21.392 (2)C9—O181.3435 (17)
C1—C61.3934 (19)C10—O161.4643 (18)
C1—C71.4900 (19)C10—C111.502 (2)
C2—C31.3945 (19)C10—H10A1.00 (2)
C2—H20.973 (19)C10—H10B1.03 (2)
C3—C41.3969 (19)C11—H11A0.98 (3)
C3—C81.491 (2)C11—H11B1.04 (3)
C4—C51.394 (2)C11—H11C1.03 (3)
C4—H41.011 (18)C12—O181.4565 (17)
C5—C61.3993 (19)C12—C131.502 (2)
C5—C91.4926 (19)C12—H12A0.940 (19)
C6—H60.99 (2)C12—H12B0.99 (2)
C7—O151.2342 (18)C13—H13A0.99 (3)
C7—O141.3064 (18)C13—H13B0.95 (2)
C8—O171.2121 (17)C13—H13C1.01 (3)
C8—O161.3401 (17)O14—H140.976 (10)
C9—O191.2038 (17)
C2—C1—C6120.69 (13)O16—C10—C11107.01 (13)
C2—C1—C7118.30 (12)O16—C10—H10A109.0 (11)
C6—C1—C7121.01 (13)C11—C10—H10A108.9 (12)
C1—C2—C3119.99 (13)O16—C10—H10B107.3 (11)
C1—C2—H2121.9 (11)C11—C10—H10B112.8 (10)
C3—C2—H2118.1 (11)H10A—C10—H10B111.7 (16)
C2—C3—C4119.79 (13)C10—C11—H11A110.6 (14)
C2—C3—C8121.91 (12)C10—C11—H11B111.5 (14)
C4—C3—C8118.29 (12)H11A—C11—H11B103 (2)
C5—C4—C3119.92 (13)C10—C11—H11C108.9 (14)
C5—C4—H4119.3 (10)H11A—C11—H11C112 (2)
C3—C4—H4120.8 (10)H11B—C11—H11C110.2 (19)
C4—C5—C6120.47 (12)O18—C12—C13106.35 (13)
C4—C5—C9121.58 (12)O18—C12—H12A109.1 (11)
C6—C5—C9117.95 (12)C13—C12—H12A110.5 (11)
C1—C6—C5119.13 (13)O18—C12—H12B109.8 (11)
C1—C6—H6118.9 (11)C13—C12—H12B109.5 (11)
C5—C6—H6122.0 (11)H12A—C12—H12B111.3 (16)
O15—C7—O14123.04 (13)C12—C13—H13A109.0 (16)
O15—C7—C1121.37 (13)C12—C13—H13B112.0 (15)
O14—C7—C1115.58 (12)H13A—C13—H13B101 (2)
O17—C8—O16123.98 (13)C12—C13—H13C112.9 (17)
O17—C8—C3123.84 (13)H13A—C13—H13C115 (2)
O16—C8—C3112.18 (12)H13B—C13—H13C106 (2)
O19—C9—O18123.89 (12)C7—O14—H14108.1 (18)
O19—C9—C5124.44 (12)C8—O16—C10115.22 (11)
O18—C9—C5111.66 (12)C9—O18—C12115.67 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O15i0.98 (1)1.67 (1)2.637 (2)171 (3)
C6—H6···O19ii0.99 (2)2.40 (2)3.378 (2)169 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z+1.
 

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