Dimethyl naphthalene-1,8-dicarboxyl­ate

In the title compound, C₁₄H₁₂O₄, the two ester groups are twisted away from the attached rings by 43.9 (2) and 41.8 (2)°. The crystal packing is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.051
• wR factor = 0.165
• Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.17
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               1183
           Count of symmetry unique reflns         1236
           Completeness (_total/calc)             95.71%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 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
   2 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-1,8-dicarboxylate

Crystal data

C14H12O4	Dx = 1.370 Mg m^−3
Mr = 244.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 20 reflections
a = 5.9561 (13) Å	θ = 4.5–5.4°
b = 12.043 (5) Å	µ = 0.10 mm^−1
c = 16.512 (6) Å	T = 293 K
V = 1184.4 (7) Å^3	Block, colourless
Z = 4	0.30 × 0.25 × 0.23 mm
F(000) = 512

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.045
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = 0→7
ω/2θ scans	k = 0→14
1343 measured reflections	l = 0→19
1183 independent reflections	3 standard reflections every 250 reflections
732 reflections with I > 2σ(I)'	intensity decay: none

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	Only H-atom displacement parameters refined
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0777P)^2 + 0.4255P] where P = (Fo^2 + 2Fc^2)/3
1183 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.29 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	0.1594 (8)	0.0842 (3)	0.8608 (2)	0.0481 (11)
O2	0.5210 (8)	0.0833 (4)	0.8218 (2)	0.0510 (12)
O3	0.4366 (8)	−0.1405 (3)	0.8766 (2)	0.0461 (11)
O4	0.7858 (9)	−0.1519 (4)	0.8240 (2)	0.0651 (13)
C1	0.4284 (11)	0.0788 (4)	0.9634 (3)	0.0415 (14)
C2	0.3182 (12)	0.1512 (4)	1.0103 (3)	0.0475 (15)
H2	0.1990	0.1903	0.9877	0.061 (8)*
C3	0.3725 (16)	0.1713 (5)	1.0915 (3)	0.064 (2)
H3	0.2865	0.2187	1.1234	0.061 (8)*
C4	0.5571 (16)	0.1183 (5)	1.1219 (3)	0.062 (2)
H4	0.6029	0.1342	1.1745	0.061 (8)*
C5	0.8696 (14)	−0.0115 (5)	1.1093 (4)	0.059 (2)
H5	0.9129	0.0051	1.1620	0.061 (8)*
C6	0.9913 (13)	−0.0855 (6)	1.0659 (4)	0.062 (2)
H6	1.1199	−0.1170	1.0882	0.061 (8)*
C7	0.9242 (13)	−0.1143 (5)	0.9885 (4)	0.0565 (18)
H7	1.0091	−0.1647	0.9588	0.061 (8)*
C8	0.7320 (11)	−0.0690 (4)	0.9547 (3)	0.0436 (14)
C9	0.6162 (11)	0.0158 (4)	0.9957 (3)	0.0414 (15)
C10	0.6793 (13)	0.0410 (4)	1.0765 (3)	0.0495 (17)
C11	0.3795 (11)	0.0803 (4)	0.8740 (4)	0.0400 (14)
C12	0.0944 (13)	0.0954 (5)	0.7772 (3)	0.0547 (18)
H12A	−0.0663	0.0979	0.7734	0.074 (9)*
H12B	0.1498	0.0330	0.7469	0.074 (9)*
H12C	0.1565	0.1626	0.7554	0.074 (9)*
C13	0.6627 (12)	−0.1220 (4)	0.8771 (4)	0.0446 (15)
C14	0.3524 (13)	−0.1894 (5)	0.8033 (3)	0.0596 (19)
H14A	0.1928	−0.1989	0.8075	0.074 (9)*
H14B	0.4222	−0.2604	0.7950	0.074 (9)*
H14C	0.3858	−0.1417	0.7583	0.074 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.047 (3)	0.057 (2)	0.040 (2)	0.001 (2)	0.002 (2)	0.0011 (19)
O2	0.047 (3)	0.067 (3)	0.039 (2)	−0.005 (2)	0.009 (3)	0.011 (2)
O3	0.047 (3)	0.048 (2)	0.044 (2)	−0.004 (2)	−0.001 (2)	−0.0081 (19)
O4	0.061 (3)	0.079 (3)	0.055 (2)	0.012 (3)	0.009 (3)	−0.022 (2)
C1	0.045 (4)	0.039 (3)	0.040 (3)	−0.007 (3)	−0.004 (3)	0.003 (2)
C2	0.053 (4)	0.047 (3)	0.042 (3)	0.004 (3)	0.005 (4)	−0.002 (3)
C3	0.103 (7)	0.048 (3)	0.042 (3)	−0.006 (4)	0.007 (4)	−0.005 (3)
C4	0.101 (7)	0.050 (3)	0.035 (3)	−0.019 (4)	0.001 (5)	−0.001 (3)
C5	0.074 (6)	0.058 (4)	0.045 (3)	−0.015 (4)	−0.011 (4)	0.004 (3)
C6	0.059 (5)	0.069 (4)	0.058 (4)	−0.007 (4)	−0.019 (4)	0.020 (3)
C7	0.059 (5)	0.052 (3)	0.058 (4)	−0.005 (3)	0.000 (4)	0.009 (3)
C8	0.043 (4)	0.046 (3)	0.042 (3)	−0.002 (3)	−0.005 (3)	0.009 (3)
C9	0.051 (4)	0.039 (3)	0.035 (3)	−0.012 (3)	−0.003 (3)	0.003 (2)
C10	0.064 (5)	0.043 (3)	0.042 (3)	−0.011 (3)	0.002 (4)	0.005 (3)
C11	0.042 (4)	0.032 (2)	0.046 (3)	−0.005 (3)	0.001 (4)	0.005 (3)
C12	0.057 (5)	0.057 (3)	0.050 (3)	−0.006 (3)	−0.010 (4)	0.006 (3)
C13	0.052 (4)	0.042 (3)	0.040 (3)	0.001 (3)	−0.003 (4)	0.005 (3)
C14	0.069 (5)	0.056 (4)	0.054 (3)	0.001 (3)	−0.013 (4)	−0.017 (3)

Geometric parameters (Å, º)

O1—C11	1.330 (7)	C5—C10	1.406 (9)
O1—C12	1.441 (6)	C5—H5	0.93
O2—C11	1.206 (7)	C6—C7	1.384 (8)
O3—C13	1.365 (8)	C6—H6	0.93
O3—C14	1.437 (6)	C7—C8	1.386 (9)
O4—C13	1.199 (7)	C7—H7	0.93
C1—C2	1.338 (8)	C8—C9	1.406 (8)
C1—C9	1.453 (9)	C8—C13	1.489 (8)
C1—C11	1.505 (8)	C9—C10	1.419 (8)
C2—C3	1.401 (7)	C12—H12A	0.96
C2—H2	0.93	C12—H12B	0.96
C3—C4	1.366 (10)	C12—H12C	0.96
C3—H3	0.93	C14—H14A	0.96
C4—C10	1.400 (9)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—C6	1.354 (9)
C11—O1—C12	115.2 (5)	C9—C8—C13	126.1 (6)
C13—O3—C14	114.7 (5)	C8—C9—C10	118.6 (6)
C2—C1—C9	120.4 (5)	C8—C9—C1	125.4 (5)
C2—C1—C11	117.7 (5)	C10—C9—C1	115.9 (5)
C9—C1—C11	121.0 (5)	C4—C10—C5	120.8 (6)
C1—C2—C3	123.6 (7)	C4—C10—C9	120.6 (7)
C1—C2—H2	118.2	C5—C10—C9	118.6 (6)
C3—C2—H2	118.2	O2—C11—O1	124.8 (6)
C4—C3—C2	117.2 (7)	O2—C11—C1	124.5 (6)
C4—C3—H3	121.4	O1—C11—C1	110.6 (6)
C2—C3—H3	121.4	O1—C12—H12A	109.5
C3—C4—C10	122.1 (6)	O1—C12—H12B	109.5
C3—C4—H4	118.9	H12A—C12—H12B	109.5
C10—C4—H4	118.9	O1—C12—H12C	109.5
C6—C5—C10	121.6 (6)	H12A—C12—H12C	109.5
C6—C5—H5	119.2	H12B—C12—H12C	109.5
C10—C5—H5	119.2	O4—C13—O3	123.3 (6)
C5—C6—C7	119.9 (7)	O4—C13—C8	126.1 (6)
C5—C6—H6	120.0	O3—C13—C8	110.4 (5)
C7—C6—H6	120.0	O3—C14—H14A	109.5
C6—C7—C8	120.8 (7)	O3—C14—H14B	109.5
C6—C7—H7	119.6	H14A—C14—H14B	109.5
C8—C7—H7	119.6	O3—C14—H14C	109.5
C7—C8—C9	119.8 (5)	H14A—C14—H14C	109.5
C7—C8—C13	114.0 (5)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2^i	0.96	2.59	3.497 (9)	158
C14—H14A···O4^i	0.96	2.50	3.422 (9)	160
C4—H4···O4^ii	0.93	2.56	3.489 (7)	173

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, −y, z+1/2.