Dimethyl naphthalene-1,4-dicarboxyl­ate

In the title compound, C₁₄H₁₂O₄, the two ester groups are twisted away from the attached ring by 25.3 (3) and 14.6 (3)°. The crystal packing is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.191
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Dimethyl naphthalene-1,4-dicarboxylate

Crystal data

C14H12O4	Z = 2
Mr = 244.24	F(000) = 256
Triclinic, P1	Dx = 1.354 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.979 (6) Å	Cell parameters from 18 reflections
b = 9.222 (4) Å	θ = 4.5–7.4°
c = 9.653 (5) Å	µ = 0.10 mm^−1
α = 75.54 (4)°	T = 291 K
β = 69.18 (5)°	Block, colourless
γ = 65.39 (4)°	0.25 × 0.22 × 0.22 mm
V = 599.3 (7) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = −8→9
ω/2θ scans	k = −7→10
2127 measured reflections	l = −10→11
2087 independent reflections	3 standard reflections every 300 reflections
1022 reflections with I > 2σ(I)	intensity decay: 1.5%

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)] = 0.059	Hydrogen site location: geom and difmap
wR(F^2) = 0.191	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.1139P)^2] where P = (Fo^2 + 2Fc^2)/3
2087 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.19 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
O1	0.5779 (4)	0.2688 (3)	0.1447 (3)	0.0914 (9)
O2	0.7570 (5)	0.4124 (4)	0.0198 (3)	0.1161 (12)
O3	−0.0250 (3)	0.7539 (3)	0.6618 (3)	0.0836 (8)
O4	0.1299 (4)	0.9167 (3)	0.6177 (3)	0.1102 (11)
C1	0.5049 (4)	0.5036 (3)	0.2404 (3)	0.0564 (8)
C2	0.3237 (5)	0.5041 (4)	0.3134 (4)	0.0623 (9)
C3	0.2014 (5)	0.6039 (4)	0.4232 (4)	0.0589 (8)
C4	0.2590 (4)	0.7032 (3)	0.4642 (3)	0.0549 (8)
C5	0.5195 (5)	0.8058 (4)	0.4289 (4)	0.0660 (9)
C6	0.6993 (5)	0.8069 (4)	0.3577 (4)	0.0745 (10)
C7	0.8201 (6)	0.7115 (4)	0.2437 (4)	0.0739 (10)
C8	0.7585 (5)	0.6159 (4)	0.2034 (4)	0.0656 (9)
C9	0.5720 (4)	0.6084 (3)	0.2752 (3)	0.0562 (8)
C10	0.4471 (4)	0.7085 (3)	0.3907 (3)	0.0537 (8)
C11	0.6294 (5)	0.3933 (4)	0.1240 (4)	0.0666 (9)
C12	0.6901 (6)	0.1535 (4)	0.0380 (5)	0.0989 (14)
H12A	0.6978	0.2084	−0.0614	0.148*
H12B	0.6297	0.0772	0.0552	0.148*
H12C	0.8173	0.0983	0.0493	0.148*
C13	0.1207 (4)	0.8029 (4)	0.5866 (4)	0.0626 (9)
C14	−0.1693 (6)	0.8400 (5)	0.7834 (5)	0.0974 (13)
H14A	−0.1079	0.8531	0.8464	0.146*
H14B	−0.2512	0.7807	0.8405	0.146*
H14C	−0.2449	0.9437	0.7443	0.146*
H2	0.288 (5)	0.440 (4)	0.283 (4)	0.079 (11)*
H3	0.073 (5)	0.608 (3)	0.474 (3)	0.069 (9)*
H5	0.433 (5)	0.867 (4)	0.515 (4)	0.095 (12)*
H6	0.747 (6)	0.865 (5)	0.397 (4)	0.109 (13)*
H7	0.950 (5)	0.719 (3)	0.190 (3)	0.066 (8)*
H8	0.832 (4)	0.552 (3)	0.132 (4)	0.066 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0827 (17)	0.0688 (15)	0.107 (2)	−0.0269 (13)	0.0069 (15)	−0.0342 (14)
O2	0.122 (2)	0.166 (3)	0.0840 (19)	−0.091 (2)	0.0194 (18)	−0.0574 (19)
O3	0.0730 (16)	0.0717 (14)	0.0965 (17)	−0.0335 (12)	0.0086 (14)	−0.0292 (13)
O4	0.0778 (18)	0.119 (2)	0.150 (3)	−0.0515 (16)	0.0093 (17)	−0.076 (2)
C1	0.0565 (19)	0.0568 (18)	0.0554 (18)	−0.0209 (15)	−0.0161 (16)	−0.0046 (15)
C2	0.062 (2)	0.063 (2)	0.068 (2)	−0.0273 (17)	−0.0180 (18)	−0.0113 (17)
C3	0.0466 (19)	0.0629 (19)	0.069 (2)	−0.0226 (15)	−0.0125 (16)	−0.0111 (16)
C4	0.0524 (18)	0.0495 (16)	0.0643 (19)	−0.0179 (14)	−0.0211 (15)	−0.0039 (14)
C5	0.058 (2)	0.0629 (19)	0.083 (2)	−0.0293 (17)	−0.0170 (19)	−0.0103 (18)
C6	0.068 (2)	0.074 (2)	0.091 (3)	−0.0376 (19)	−0.018 (2)	−0.012 (2)
C7	0.067 (2)	0.075 (2)	0.086 (2)	−0.0425 (19)	−0.014 (2)	−0.002 (2)
C8	0.058 (2)	0.069 (2)	0.064 (2)	−0.0269 (17)	−0.0092 (18)	−0.0054 (19)
C9	0.0575 (19)	0.0569 (17)	0.0540 (17)	−0.0249 (15)	−0.0169 (15)	0.0026 (15)
C10	0.0491 (17)	0.0500 (16)	0.0628 (18)	−0.0205 (14)	−0.0193 (15)	0.0014 (14)
C11	0.060 (2)	0.085 (2)	0.057 (2)	−0.0301 (18)	−0.0122 (18)	−0.0125 (18)
C12	0.099 (3)	0.064 (2)	0.108 (3)	−0.015 (2)	−0.002 (2)	−0.037 (2)
C13	0.0534 (19)	0.0549 (18)	0.079 (2)	−0.0197 (15)	−0.0166 (17)	−0.0112 (17)
C14	0.077 (3)	0.096 (3)	0.110 (3)	−0.033 (2)	0.011 (2)	−0.049 (2)

Geometric parameters (Å, º)

O1—C11	1.321 (4)	C5—C10	1.423 (4)
O1—C12	1.447 (4)	C5—H5	0.99 (4)
O2—C11	1.188 (4)	C6—C7	1.392 (5)
O3—C13	1.325 (4)	C6—H6	0.98 (4)
O3—C14	1.442 (4)	C7—C8	1.356 (5)
O4—C13	1.197 (4)	C7—H7	1.00 (3)
C1—C2	1.363 (5)	C8—C9	1.424 (5)
C1—C9	1.433 (4)	C8—H8	0.89 (3)
C1—C11	1.490 (4)	C9—C10	1.431 (4)
C2—C3	1.388 (5)	C12—H12A	0.96
C2—H2	0.90 (4)	C12—H12B	0.96
C3—C4	1.367 (4)	C12—H12C	0.96
C3—H3	0.95 (3)	C14—H14A	0.96
C4—C10	1.430 (4)	C14—H14B	0.96
C4—C13	1.494 (4)	C14—H14C	0.96
C5—C6	1.356 (5)
C11—O1—C12	116.6 (3)	C9—C8—H8	115 (2)
C13—O3—C14	117.9 (3)	C8—C9—C10	117.9 (3)
C2—C1—C9	120.2 (3)	C8—C9—C1	123.6 (3)
C2—C1—C11	118.6 (3)	C10—C9—C1	118.5 (3)
C9—C1—C11	121.2 (3)	C5—C10—C4	123.4 (3)
C1—C2—C3	121.2 (3)	C5—C10—C9	117.7 (3)
C1—C2—H2	116 (2)	C4—C10—C9	118.9 (3)
C3—C2—H2	123 (2)	O2—C11—O1	121.6 (3)
C4—C3—C2	121.3 (3)	O2—C11—C1	126.3 (3)
C4—C3—H3	116.0 (18)	O1—C11—C1	112.1 (3)
C2—C3—H3	122.6 (18)	O1—C12—H12A	109.5
C3—C4—C10	119.9 (3)	O1—C12—H12B	109.5
C3—C4—C13	117.9 (3)	H12A—C12—H12B	109.5
C10—C4—C13	122.2 (3)	O1—C12—H12C	109.5
C6—C5—C10	121.8 (4)	H12A—C12—H12C	109.5
C6—C5—H5	122 (2)	H12B—C12—H12C	109.5
C10—C5—H5	116 (2)	O4—C13—O3	120.8 (3)
C5—C6—C7	120.6 (4)	O4—C13—C4	127.0 (3)
C5—C6—H6	118 (2)	O3—C13—C4	112.2 (3)
C7—C6—H6	121 (2)	O3—C14—H14A	109.5
C8—C7—C6	120.0 (4)	O3—C14—H14B	109.5
C8—C7—H7	121.3 (17)	H14A—C14—H14B	109.5
C6—C7—H7	118.6 (17)	O3—C14—H14C	109.5
C7—C8—C9	122.0 (4)	H14A—C14—H14C	109.5
C7—C8—H8	123 (2)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.90 (4)	2.33 (4)	2.688 (5)	104 (3)
C3—H3···O3	0.96 (4)	2.25 (3)	2.652 (5)	105 (3)
C5—H5···O4	0.99 (4)	2.15 (4)	2.879 (6)	128 (3)
C6—H6···O4^i	0.98 (5)	2.54 (5)	3.440 (6)	154 (3)
C7—H7···O2^ii	1.00 (4)	2.56 (3)	3.362 (6)	137 (2)
C8—H8···O2	0.89 (3)	2.23 (3)	2.891 (6)	130 (3)

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