4-(2-Naphth­yl)pyrimidine

The title compound, C₁₄H₁₀N₂, has been synthesized from the appropriate ketones and formamide using different palladium complexes as catalysts. The pyrimidine group is twisted 30.48 (9)° relative to the naphthalene part of the mol­ecule, resulting in an intramolecular C—H...N hydrogen bond. There is also an intermolecular C—H...N hydrogen bond linking the mol­ecules in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.097
• Data-to-parameter ratio = 9.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.90 Deg.

Author Response: see _publ_section_exptl_refinement

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.80
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  C11     ..       2.82 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C14    ..  N2      ..      99.00 Deg.

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).

4-(2-Naphthyl)pyrimidine

Crystal data

C14H10N2	F(000) = 432
Mr = 206.24	Dx = 1.321 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71069 Å
a = 7.4467 (16) Å	Cell parameters from 25 reflections
b = 6.1343 (11) Å	θ = 12–18°
c = 22.720 (3) Å	µ = 0.08 mm^−1
β = 92.508 (19)°	T = 298 K
V = 1036.9 (3) Å^3	Plate, white
Z = 4	0.50 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	586 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.008
Graphite monochromator	θmax = 24.9°, θmin = 1.8°
ω–2θ scans	h = −2→8
Absorption correction: ψ scan [North et al., 1968) and ABSCALC in OSCAIL (McArdle & Daly, 1999)]	k = 0→7
Tmin = 0.961, Tmax = 0.992	l = −26→26
1984 measured reflections	3 standard reflections every 120 min
1813 independent reflections	intensity decay: 2%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	All H-atom parameters refined
S = 0.82	w = 1/[σ^2(Fo^2) + (0.0341P)^2] where P = (Fo^2 + 2Fc^2)/3
1813 reflections	(Δ/σ)max = 0.035
185 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.17 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 7.0770 (0.0039) x + 0.0143 (0.0099) y + 8.0080 (0.0290) z = 1.3900 (0.0077)

* -0.0009 (0.0023) N2 * 0.0013 (0.0028) C1 * 0.0035 (0.0027) N1 * -0.0083 (0.0029) C2 * 0.0083 (0.0026) C3 * -0.0038 (0.0022) C4 0.0147 (0.0051) C5

Rms deviation of fitted atoms = 0.0053

6.6260 (0.0036) x + 2.7788 (0.0046) y - 2.1426 (0.0130) z = 1.4254 (0.0047)

Angle to previous plane (with approximate e.s.d.) = 30.48 (0.09)

* -0.0283 (0.0025) C5 * -0.0055 (0.0026) C6 * 0.0221 (0.0028) C7 * 0.0145 (0.0028) C8 * -0.0021 (0.0031) C9 * -0.0191 (0.0031) C10 * -0.0098 (0.0028) C11 * 0.0069 (0.0028) C12 * 0.0188 (0.0029) C13 * 0.0027 (0.0026) C14 - 0.1351 (0.0043) C4

Rms deviation of fitted atoms = 0.0155

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
N2	−0.0627 (4)	0.4682 (4)	0.11710 (11)	0.0531 (8)
N1	−0.1464 (4)	0.7324 (6)	0.04330 (12)	0.0653 (9)
H1	−0.153 (4)	0.412 (5)	0.0396 (13)	0.063 (11)*
H14	0.162 (4)	0.280 (4)	0.1833 (12)	0.039 (8)*
H6	−0.042 (3)	0.818 (4)	0.2587 (11)	0.043 (10)*
H10	0.201 (4)	0.401 (4)	0.4754 (13)	0.057 (10)*
H13	0.256 (4)	0.139 (5)	0.2784 (12)	0.061 (11)*
H9	0.053 (4)	0.749 (5)	0.4633 (13)	0.073 (12)*
H8	−0.021 (4)	0.872 (5)	0.3682 (12)	0.052 (11)*
H11	0.258 (4)	0.170 (6)	0.3863 (13)	0.075 (12)*
H3	−0.006 (4)	0.963 (5)	0.1641 (11)	0.048 (9)*
H2	−0.127 (4)	1.047 (5)	0.0651 (13)	0.071 (11)*
C1	−0.1235 (6)	0.5307 (7)	0.06378 (16)	0.0641 (12)
C2	−0.1008 (5)	0.8877 (7)	0.08208 (16)	0.0633 (11)
C3	−0.0383 (5)	0.8425 (6)	0.13905 (16)	0.0486 (10)
C4	−0.0192 (4)	0.6288 (6)	0.15519 (13)	0.0388 (8)
C5	0.0458 (4)	0.5591 (5)	0.21478 (14)	0.0375 (8)
C6	0.0145 (4)	0.6798 (6)	0.26364 (14)	0.0391 (9)
C7	0.0683 (4)	0.6056 (6)	0.32077 (14)	0.0394 (9)
C8	0.0328 (4)	0.7266 (7)	0.37187 (15)	0.0499 (10)
C9	0.0800 (5)	0.6501 (8)	0.42668 (16)	0.0624 (13)
C10	0.1652 (5)	0.4463 (8)	0.43285 (17)	0.0663 (13)
C11	0.2023 (5)	0.3240 (7)	0.38488 (17)	0.0539 (11)
C12	0.1535 (4)	0.4017 (6)	0.32712 (14)	0.0428 (9)
C13	0.1897 (5)	0.2801 (6)	0.27600 (15)	0.0475 (10)
C14	0.1371 (4)	0.3576 (6)	0.22151 (15)	0.0435 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.065 (2)	0.053 (2)	0.0402 (17)	−0.0025 (17)	−0.0116 (15)	−0.0075 (16)
N1	0.085 (2)	0.061 (2)	0.0483 (19)	0.006 (2)	−0.0113 (17)	0.004 (2)
C1	0.087 (3)	0.055 (3)	0.049 (3)	−0.002 (3)	−0.016 (2)	−0.009 (2)
C2	0.078 (3)	0.053 (3)	0.059 (3)	0.007 (3)	0.002 (2)	0.013 (2)
C3	0.054 (2)	0.041 (2)	0.051 (2)	−0.003 (2)	−0.0005 (19)	−0.003 (2)
C4	0.040 (2)	0.037 (2)	0.039 (2)	0.0001 (19)	−0.0018 (16)	−0.0031 (18)
C5	0.0306 (19)	0.040 (2)	0.042 (2)	−0.0026 (18)	0.0015 (16)	−0.0025 (17)
C6	0.036 (2)	0.030 (2)	0.050 (3)	0.0011 (18)	−0.0050 (18)	0.0003 (17)
C7	0.0266 (19)	0.049 (2)	0.043 (2)	−0.0011 (19)	−0.0013 (16)	0.0007 (18)
C8	0.040 (2)	0.063 (3)	0.047 (3)	−0.002 (2)	−0.0015 (19)	−0.006 (2)
C9	0.045 (2)	0.098 (4)	0.044 (3)	0.002 (3)	−0.002 (2)	−0.006 (3)
C10	0.051 (3)	0.105 (4)	0.043 (3)	−0.005 (3)	−0.003 (2)	0.012 (3)
C11	0.038 (2)	0.060 (3)	0.064 (3)	−0.006 (2)	−0.003 (2)	0.015 (2)
C12	0.031 (2)	0.050 (2)	0.047 (2)	−0.0068 (19)	−0.0057 (17)	0.0088 (19)
C13	0.040 (2)	0.043 (3)	0.059 (3)	0.004 (2)	0.001 (2)	0.002 (2)
C14	0.036 (2)	0.047 (2)	0.048 (2)	−0.003 (2)	0.0067 (18)	−0.007 (2)

Geometric parameters (Å, º)

N2—C1	1.331 (4)	C7—C12	1.407 (4)
N2—C4	1.341 (3)	C7—C8	1.413 (4)
N1—C1	1.330 (4)	C8—C9	1.362 (4)
N1—C2	1.331 (4)	C8—H8	0.98 (3)
C1—H1	0.93 (3)	C9—C10	1.406 (5)
C2—C3	1.384 (5)	C9—H9	1.05 (3)
C2—H2	1.07 (3)	C10—C11	1.361 (5)
C3—C4	1.367 (4)	C10—H10	1.03 (3)
C3—H3	0.96 (3)	C11—C12	1.428 (4)
C4—C5	1.481 (4)	C11—H11	1.03 (3)
C5—C6	1.363 (4)	C12—C13	1.416 (4)
C5—C14	1.416 (4)	C13—C14	1.367 (4)
C6—C7	1.417 (4)	C13—H13	1.00 (3)
C6—H6	0.95 (3)	C14—H14	1.01 (3)
C1—N2—C4	116.0 (3)	C8—C7—C6	121.9 (3)
C1—N1—C2	114.1 (3)	C9—C8—C7	121.3 (4)
N1—C1—N2	128.3 (4)	C9—C8—H8	118.7 (17)
N1—C1—H1	119.9 (19)	C7—C8—H8	119.9 (17)
N2—C1—H1	111.8 (19)	C8—C9—C10	119.6 (4)
N1—C2—C3	122.8 (4)	C8—C9—H9	118.3 (17)
N1—C2—H2	112.3 (17)	C10—C9—H9	122.1 (17)
C3—C2—H2	124.8 (17)	C11—C10—C9	121.1 (4)
C4—C3—C2	118.0 (4)	C11—C10—H10	123.2 (17)
C4—C3—H3	124.1 (17)	C9—C10—H10	115.6 (16)
C2—C3—H3	117.9 (17)	C10—C11—C12	120.0 (4)
N2—C4—C3	120.8 (3)	C10—C11—H11	125.1 (18)
N2—C4—C5	116.0 (3)	C12—C11—H11	114.9 (18)
C3—C4—C5	123.2 (3)	C7—C12—C13	119.0 (3)
C6—C5—C14	119.0 (3)	C7—C12—C11	119.1 (4)
C6—C5—C4	121.8 (3)	C13—C12—C11	121.9 (4)
C14—C5—C4	119.1 (3)	C14—C13—C12	120.2 (4)
C5—C6—C7	121.3 (3)	C14—C13—H13	118.2 (16)
C5—C6—H6	118.7 (16)	C12—C13—H13	121.6 (17)
C7—C6—H6	120.0 (16)	C13—C14—C5	121.2 (4)
C12—C7—C8	118.9 (3)	C13—C14—H14	123.7 (15)
C12—C7—C6	119.2 (3)	C5—C14—H14	115.0 (15)
C2—N1—C1—N2	0.3 (6)	C12—C7—C8—C9	0.3 (5)
C4—N2—C1—N1	0.1 (6)	C6—C7—C8—C9	177.8 (3)
C1—N1—C2—C3	−1.2 (6)	C7—C8—C9—C10	−0.3 (5)
N1—C2—C3—C4	1.6 (6)	C8—C9—C10—C11	0.4 (6)
C1—N2—C4—C3	0.3 (5)	C9—C10—C11—C12	−0.4 (5)
C1—N2—C4—C5	179.1 (3)	C8—C7—C12—C13	−179.9 (3)
C2—C3—C4—N2	−1.1 (5)	C6—C7—C12—C13	2.6 (4)
C2—C3—C4—C5	−179.8 (3)	C8—C7—C12—C11	−0.4 (4)
N2—C4—C5—C6	−148.1 (3)	C6—C7—C12—C11	−178.0 (3)
C3—C4—C5—C6	30.7 (5)	C10—C11—C12—C7	0.4 (5)
N2—C4—C5—C14	29.5 (4)	C10—C11—C12—C13	179.9 (3)
C3—C4—C5—C14	−151.7 (3)	C7—C12—C13—C14	−2.1 (5)
C14—C5—C6—C7	−1.3 (4)	C11—C12—C13—C14	178.5 (3)
C4—C5—C6—C7	176.4 (3)	C12—C13—C14—C5	−0.1 (5)
C5—C6—C7—C12	−0.9 (4)	C6—C5—C14—C13	1.8 (5)
C5—C6—C7—C8	−178.4 (3)	C4—C5—C14—C13	−175.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N2	1.01 (2)	2.49 (3)	2.827 (4)	99 (2)
C1—H1···N1^i	0.93 (2)	2.60 (3)	3.440 (5)	151 (2)
C13—H13···C6^ii	1.00 (2)	2.78 (3)	3.735 (5)	163 (2)
C8—H8···C11^iii	0.98 (2)	2.82 (3)	3.716 (3)	153 (2)

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