In the crystal structure of the title compound, C
13H
14O
6, 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
CCDC reference: 629635
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (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
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
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) Å3 | 0.45 × 0.30 × 0.15 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | All 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 parameters | Δρmax = 0.46 e Å−3 |
1 restraint | Δρmin = −0.34 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···O15i | 0.98 (1) | 1.67 (1) | 2.637 (2) | 171 (3) |
C6—H6···O19ii | 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. |