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The crystal structures of 2,6-naphthalenedicarboxylic acid (NDA) and dimethyl 2,6-naphthalenedicarboxylate (NDC) have been solved ab initio using a combination of X-ray powder diffraction and computational chemistry techniques. These two crystal structures, and that of 2,6-dimethylnaphthalene (DMN), have been refined by the Rietveld technique. DMN crystallizes in the orthorhombic space group Pbca, with a = 7.4544 (4), b = 6.0826 (6), c = 20.0946 (12) Å, V = 911.1 (1) Å3 and Z = 4. The structure consists of a herringbone stacking parallel to a, resulting in loosely bound layers perpendicular to c. NDA crystallizes in the triclinic space group P1, with a = 3.7061 (8), b = 7.4688 (14), c = 8.5352 (22) Å, α = 86.62 (2), β = 85.49 (2), γ = 87.99 (2)°, V = 235.00 (6) Å3 and Z = 1. The structure consists of loosely packed hydrogen-bonded chains along [111]. NDC crystallizes in the monoclinic space group P21/c, with a = 13.41931 (14), b = 6.14869 (5), c = 7.15257 (5) Å, β = 100.400 (1)°, V = 580.47 (1) Å3 at 300 K and Z = 2. The structure consists of layers of NDC molecules perpendicular to a. The ester group is twisted 20° out of the mean ring plane in NDC. The conformations of the carboxyl groups in NDA and NDC differ. MP2 calculations suggest that the observed twist in NDC corresponds to an increase in conformational energy of 9 kJ mol−1.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks text, dmn, nda, ndc

rtv

Rietveld powder data file (CIF format)
Contains datablocks kadu216, _overall, KADU216_phase_1, KADU216_phase_2, KADU216_phase_3

rtv

Rietveld powder data file (CIF format)
Contains datablocks edlu06, _overall, EDLU06_phase_1

rtv

Rietveld powder data file (CIF format)
Contains datablocks publ, _overall, YMC_phase_1, YMC_phase_2

CCDC references: 131744; 131745; 131746

Computing details top

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(dmn) top
Crystal data top
C12H12c = 20.0946 (12) Å
Mr = 156V = 911.12 (11) Å3
Orthorhombic, PbcaZ = 4
Hall symbol: -P 2ac 2abCu radiation, λ = 1.5406 Å
a = 7.4544 (4) Å × × mm
b = 6.0826 (6) Å
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C12H12c = 20.0946 (12) Å
Mr = 156V = 911.12 (11) Å3
Orthorhombic, PbcaZ = 4
a = 7.4544 (4) ÅCu radiation, λ = 1.5406 Å
b = 6.0826 (6) Å × × mm
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0747 (7)0.2245 (5)0.05524 (16)0.0327 (14)
C20.0291 (7)0.1401 (7)0.11735 (10)0.0327 (14)
C30.0501 (8)0.0665 (7)0.12223 (11)0.0327 (14)
C40.0836 (5)0.1887 (5)0.06499 (17)0.0327 (14)
C50.0379 (8)0.1043 (6)0.00288 (12)0.0327 (14)
C60.0691 (9)0.2765 (11)0.1796 (2)0.0327 (14)
H10.137270.361940.052230.05
H30.084990.123380.164860.05
H40.140770.329560.068040.05
H6a0.025820.197590.218820.05
H6b0.003170.413300.176550.05
H6c0.192330.303540.183140.05
Geometric parameters (Å, º) top
C2—C11.392C2—C31.392
C2—C61.530 (3)C3—C41.392
C4—C51.392C5—C5i1.394 (4)
C5—C1i1.405 (3)
C3—C2—C1120C3—C2—C6121.0 (3)
C1—C2—C6119.0 (3)C2—C3—C4120
C3—C4—C5120C4—C5—C5i120.6 (1)
C4—C5—C1i120.4 (2)C5—C5i—C1119.0 (2)
C2—C1—C5i120.4 (2)
Symmetry code: (i) x, y, z.
(nda) top
Crystal data top
C12H8O4α = 86.62 (2)°
Mr = 216β = 85.49 (2)°
Triclinic, P1γ = 87.99 (2)°
Hall symbol: -P 1V = 235.00 (6) Å3
a = 3.7061 (8) ÅZ = 1
b = 7.4688 (14) ÅCu radiation, λ = 1.5406 Å
c = 8.535 (2) Å × × mm
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C12H8O4β = 85.49 (2)°
Mr = 216γ = 87.99 (2)°
Triclinic, P1V = 235.00 (6) Å3
a = 3.7061 (8) ÅZ = 1
b = 7.4688 (14) ÅCu radiation, λ = 1.5406 Å
c = 8.535 (2) Å × × mm
α = 86.62 (2)°
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.619 (5)0.2666 (5)0.5718 (10)0.05
C20.663 (4)0.2945 (9)0.7289 (8)0.05
C30.636 (4)0.4675 (12)0.7819 (6)0.05
C40.564 (3)0.6126 (8)0.6779 (8)0.05
C50.520 (5)0.5848 (5)0.5208 (9)0.05
C70.763 (5)0.1425 (12)0.8485 (11)0.05
O10.915 (4)0.0095 (13)0.8015 (12)0.05
O20.889 (4)0.2036 (11)0.9812 (11)0.05
H10.695020.155990.529710.08
H20.95390.13341.05580.08
H30.672040.494830.888730.08
H40.541910.736610.710970.08
Geometric parameters (Å, º) top
C2—C11.392C2—C31.392
C2—C71.537 (6)C1—C5i1.428 (7)
C3—C41.392C4—C51.392
C5—C5i1.351 (8)C7—O11.198 (9)
C7—O21.366 (9)
C2—C1—C5i116.8 (5)C1—C2—C3120
C1—C2—C7123.0 (5)C3—C2—C7116.9 (6)
C2—C3—C4120C3—C4—C5120
C4—C5—C5i118.4 (5)C4—C5—C1i120.3 (5)
C2—C7—O1119.0 (9)C2—C7—O2113.0 (9)
O1—C7—O2115.1 (9)
Symmetry code: (i) x+1, y+1, z+1.
(ndc) top
Crystal data top
C14H12O4c = 7.15257 (5) Å
Mr = 244β = 100.400 (1)°
Monoclinic, P21/cV = 580.47 (1) Å3
Hall symbol: -P 2ybcZ = 2
a = 13.41931 (14) ÅSynchrotron radiation, λ = 1.15023 Å
b = 6.14869 (5) Å × × mm
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C14H12O4β = 100.400 (1)°
Mr = 244V = 580.47 (1) Å3
Monoclinic, P21/cZ = 2
a = 13.41931 (14) ÅSynchrotron radiation, λ = 1.15023 Å
b = 6.14869 (5) Å × × mm
c = 7.15257 (5) Å
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1040 (2)0.1874 (4)0.1007 (5)0.018 (1)
C20.1894 (1)0.0634 (6)0.0889 (5)0.018 (1)
C30.1786 (2)0.1450 (6)0.0118 (5)0.018 (1)
C40.0824 (2)0.2294 (3)0.0536 (3)0.018 (1)
C50.0030 (2)0.1054 (5)0.0418 (6)0.018 (1)
C70.2961 (4)0.1447 (9)0.1564 (9)0.065 (1)
C80.3995 (5)0.4521 (8)0.2158 (9)0.065 (1)
O10.3679 (4)0.0283 (5)0.1824 (6)0.065 (1)
O20.2968 (4)0.3610 (6)0.1662 (6)0.065 (1)
H10.109880.327320.162920.08
H30.236560.220090.007270.08
H40.074690.363320.119180.08
H8a0.396780.604280.220050.08
H8b0.433340.407410.111850.08
H8c0.434000.391210.330000.08
Geometric parameters (Å, º) top
C2—C11.392C2—C31.392
C2—C71.510 (5)C3—C41.392
C4—C51.392C5—C5i1.423 (5)
C5—C1i1.436 (4)C7—O11.188 (5)
C7—O21.332 (5)O2—C81.470 (5)
C1—C2—C3120C1—C2—C7122.9 (2)
C3—C2—C7117.1 (2)C2—C3—C4120
C3—C4—C5120C4—C5—C5i122.6 (1)
C4—C5—C1i122.3 (3)C1i—C5—C5i114.9 (3)
C2—C1—C5i122.3 (2)C2—C7—O1123.1 (5)
C2—C7—O2110.2 (5)O1—C7—O2126.5 (5)
C7—O2—C8113.0 (5)
Symmetry code: (i) x, y, z.

Experimental details

(dmn)(nda)(ndc)
Crystal data
Chemical formulaC12H12C12H8O4C14H12O4
Mr156216244
Crystal system, space groupOrthorhombic, PbcaTriclinic, P1Monoclinic, P21/c
Temperature (K)???
a, b, c (Å)7.4544 (4), 6.0826 (6), 20.0946 (12)3.7061 (8), 7.4688 (14), 8.535 (2)13.41931 (14), 6.14869 (5), 7.15257 (5)
α, β, γ (°)90, 90, 9086.62 (2), 85.49 (2), 87.99 (2)90, 100.400 (1), 90
V3)911.12 (11)235.00 (6)580.47 (1)
Z412
Radiation typeCu, λ = 1.5406 ÅCu, λ = 1.5406 ÅSynchrotron, λ = 1.15023 Å
µ (mm1)???
Crystal size (mm) × × × × × ×
Data collection
Diffractometer???
Absorption correction???
No. of measured, independent and
observed (?) reflections
?, ?, ? ?, ?, ? ?, ?, ?
Rint???
Refinement
R[F2 > 2σ(F2)], wR(F2), S ?, ?, ? ?, ?, ? ?, ?, ?
No. of reflections???
No. of parameters???
No. of restraints???
Δρmax, Δρmin (e Å3)?, ??, ??, ?

Selected geometric parameters (Å, º) for (dmn) top
C2—C11.392C2—C31.392
C2—C61.530 (3)C3—C41.392
C4—C51.392C5—C5i1.394 (4)
C5—C1i1.405 (3)
C3—C2—C1120C3—C2—C6121.0 (3)
C1—C2—C6119.0 (3)C2—C3—C4120
C3—C4—C5120C4—C5—C5i120.6 (1)
C4—C5—C1i120.4 (2)C5—C5i—C1119.0 (2)
C2—C1—C5i120.4 (2)
Symmetry code: (i) x, y, z.
Selected geometric parameters (Å, º) for (nda) top
C2—C11.392C2—C31.392
C2—C71.537 (6)C1—C5i1.428 (7)
C3—C41.392C4—C51.392
C5—C5i1.351 (8)C7—O11.198 (9)
C7—O21.366 (9)
C2—C1—C5i116.8 (5)C1—C2—C3120
C1—C2—C7123.0 (5)C3—C2—C7116.9 (6)
C2—C3—C4120C3—C4—C5120
C4—C5—C5i118.4 (5)C4—C5—C1i120.3 (5)
C2—C7—O1119.0 (9)C2—C7—O2113.0 (9)
O1—C7—O2115.1 (9)
Symmetry code: (i) x+1, y+1, z+1.
Selected geometric parameters (Å, º) for (ndc) top
C2—C11.392C2—C31.392
C2—C71.510 (5)C3—C41.392
C4—C51.392C5—C5i1.423 (5)
C5—C1i1.436 (4)C7—O11.188 (5)
C7—O21.332 (5)O2—C81.470 (5)
C1—C2—C3120C1—C2—C7122.9 (2)
C3—C2—C7117.1 (2)C2—C3—C4120
C3—C4—C5120C4—C5—C5i122.6 (1)
C4—C5—C1i122.3 (3)C1i—C5—C5i114.9 (3)
C2—C1—C5i122.3 (2)C2—C7—O1123.1 (5)
C2—C7—O2110.2 (5)O1—C7—O2126.5 (5)
C7—O2—C8113.0 (5)
Symmetry code: (i) x, y, z.
 
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