3-(N-Phthalimidometh­yl)pyridine

In the crystal structure of the title compound, C₁₄H₁₀N₂O₂, there are strong π–π inter­actions between mol­ecules, resulting in a one-dimensional chain structure.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.062
• wR factor = 0.160
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.72
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H10 N2 O2

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: SAINT and SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-(N-Phthalimidomethyl)pyridine

Crystal data

C14H10N2O2	Z = 2
Mr = 238.24	F(000) = 248
Triclinic, P1	Dx = 1.413 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.13 (4) Å	Cell parameters from 62 reflections
b = 8.05 (4) Å	θ = 2.7–27.5°
c = 10.57 (7) Å	µ = 0.10 mm^−1
α = 91.84 (8)°	T = 130 K
β = 100.53 (9)°	Prism, white
γ = 109.15 (10)°	0.55 × 0.20 × 0.10 mm
V = 561 (6) Å^3

Data collection

Bruker SMART diffractometer	2526 independent reflections
Radiation source: fine-focus sealed tube	1950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 14.6306 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −9→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→10
Tmin = 0.977, Tmax = 0.990	l = −13→12
4353 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0723P)^2 + 0.2262P] where P = (Fo^2 + 2Fc^2)/3
2526 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.27 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	0.2128 (3)	0.0485 (3)	−0.2875 (2)	0.0683 (7)
O2	0.2697 (2)	0.50744 (17)	0.00005 (15)	0.0330 (4)
N1	−0.2884 (3)	0.4541 (3)	−0.36944 (19)	0.0490 (6)
N2	0.2406 (2)	0.3039 (2)	−0.16811 (17)	0.0316 (4)
C1	0.2670 (3)	0.2076 (2)	0.0352 (2)	0.0260 (4)
C2	0.2477 (3)	0.0680 (3)	−0.0526 (2)	0.0373 (6)
C3	0.2485 (3)	−0.0936 (3)	−0.0113 (3)	0.0565 (9)
H3	0.2351	−0.1874	−0.0700	0.068*
C4	0.2699 (3)	−0.1111 (3)	0.1192 (3)	0.0592 (9)
H4	0.2725	−0.2179	0.1492	0.071*
C5	0.2876 (3)	0.0279 (3)	0.2064 (3)	0.0489 (7)
H5	0.3002	0.0119	0.2939	0.059*
C6	0.2869 (3)	0.1918 (3)	0.1663 (2)	0.0332 (5)
H6	0.2993	0.2854	0.2249	0.040*
C7	0.2310 (3)	0.1278 (3)	−0.1835 (2)	0.0410 (6)
C8	0.2599 (3)	0.3606 (2)	−0.03866 (19)	0.0242 (4)
C9	−0.0966 (3)	0.4762 (4)	−0.3108 (2)	0.0459 (6)
H9	−0.0368	0.5611	−0.2402	0.055*
C10	0.0187 (3)	0.3810 (3)	−0.3485 (2)	0.0370 (5)
C11	−0.0701 (3)	0.2554 (3)	−0.4542 (2)	0.0351 (5)
H11	0.0022	0.1897	−0.4832	0.042*
C12	−0.2686 (3)	0.2290 (3)	−0.5163 (2)	0.0378 (5)
H12	−0.3318	0.1450	−0.5871	0.045*
C13	−0.3704 (3)	0.3304 (3)	−0.4706 (2)	0.0409 (6)
H13	−0.5034	0.3115	−0.5125	0.049*
C14	0.2336 (3)	0.4161 (4)	−0.2738 (2)	0.0415 (6)
H14A	0.3153	0.3954	−0.3325	0.050*
H14B	0.2922	0.5392	−0.2387	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0549 (11)	0.0935 (15)	0.0589 (13)	0.0505 (11)	−0.0208 (9)	−0.0440 (11)
O2	0.0353 (8)	0.0229 (7)	0.0414 (9)	0.0130 (6)	0.0043 (6)	0.0007 (6)
N1	0.0320 (10)	0.0851 (16)	0.0332 (11)	0.0298 (10)	−0.0010 (8)	−0.0109 (10)
N2	0.0245 (8)	0.0413 (10)	0.0293 (9)	0.0157 (7)	−0.0006 (7)	−0.0035 (7)
C1	0.0156 (8)	0.0190 (9)	0.0396 (12)	0.0052 (7)	−0.0022 (7)	0.0013 (8)
C2	0.0187 (9)	0.0254 (10)	0.0614 (15)	0.0104 (8)	−0.0109 (9)	−0.0084 (10)
C3	0.0269 (11)	0.0229 (11)	0.107 (3)	0.0131 (9)	−0.0217 (13)	−0.0121 (13)
C4	0.0229 (11)	0.0254 (11)	0.114 (3)	0.0036 (9)	−0.0162 (13)	0.0193 (14)
C5	0.0202 (10)	0.0451 (14)	0.0704 (18)	0.0038 (9)	−0.0079 (10)	0.0295 (13)
C6	0.0193 (9)	0.0322 (10)	0.0439 (13)	0.0067 (8)	−0.0009 (8)	0.0088 (9)
C7	0.0257 (10)	0.0482 (13)	0.0465 (14)	0.0221 (10)	−0.0123 (9)	−0.0219 (11)
C8	0.0173 (8)	0.0242 (9)	0.0299 (10)	0.0078 (7)	0.0011 (7)	0.0001 (7)
C9	0.0305 (11)	0.0810 (18)	0.0270 (12)	0.0258 (12)	−0.0022 (9)	−0.0114 (12)
C10	0.0255 (10)	0.0645 (15)	0.0227 (10)	0.0176 (10)	0.0047 (8)	0.0065 (10)
C11	0.0310 (11)	0.0561 (14)	0.0255 (10)	0.0218 (10)	0.0100 (8)	0.0082 (10)
C12	0.0320 (11)	0.0598 (15)	0.0233 (10)	0.0195 (10)	0.0032 (8)	0.0015 (10)
C13	0.0258 (10)	0.0723 (17)	0.0263 (11)	0.0226 (11)	−0.0001 (8)	−0.0026 (11)
C14	0.0263 (10)	0.0727 (17)	0.0279 (11)	0.0201 (11)	0.0047 (9)	0.0085 (11)

Geometric parameters (Å, º)

O1—C7	1.218 (7)	C4—H4	0.9300
O2—C8	1.214 (6)	C5—C6	1.400 (7)
N1—C13	1.341 (6)	C5—H5	0.9300
N1—C9	1.345 (7)	C6—H6	0.9300
N2—C8	1.396 (9)	C9—C10	1.390 (5)
N2—C7	1.399 (7)	C9—H9	0.9300
N2—C14	1.462 (7)	C10—C11	1.386 (7)
C1—C6	1.381 (10)	C10—C14	1.519 (7)
C1—C2	1.388 (6)	C11—C12	1.390 (7)
C1—C8	1.489 (6)	C11—H11	0.9300
C2—C3	1.386 (7)	C12—C13	1.384 (5)
C2—C7	1.477 (9)	C12—H12	0.9300
C3—C4	1.377 (10)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.384 (7)	C14—H14B	0.9700
C13—N1—C9	116.3 (3)	O2—C8—N2	124.5 (2)
C8—N2—C7	111.6 (2)	O2—C8—C1	129.5 (4)
C8—N2—C14	123.90 (19)	N2—C8—C1	105.95 (18)
C7—N2—C14	124.5 (3)	N1—C9—C10	124.5 (4)
C6—C1—C2	121.9 (4)	N1—C9—H9	117.7
C6—C1—C8	130.3 (2)	C10—C9—H9	117.7
C2—C1—C8	107.9 (2)	C11—C10—C9	117.6 (3)
C3—C2—C1	120.9 (2)	C11—C10—C14	122.5 (2)
C3—C2—C7	130.7 (2)	C9—C10—C14	119.9 (4)
C1—C2—C7	108.4 (4)	C10—C11—C12	119.1 (2)
C4—C3—C2	118.0 (3)	C10—C11—H11	120.5
C4—C3—H3	121.0	C12—C11—H11	120.5
C2—C3—H3	121.0	C13—C12—C11	118.7 (4)
C3—C4—C5	121.0 (4)	C13—C12—H12	120.7
C3—C4—H4	119.5	C11—C12—H12	120.7
C5—C4—H4	119.5	N1—C13—C12	123.8 (3)
C4—C5—C6	121.7 (5)	N1—C13—H13	118.1
C4—C5—H5	119.2	C12—C13—H13	118.1
C6—C5—H5	119.2	N2—C14—C10	112.4 (3)
C1—C6—C5	116.6 (2)	N2—C14—H14A	109.1
C1—C6—H6	121.7	C10—C14—H14A	109.1
C5—C6—H6	121.7	N2—C14—H14B	109.1
O1—C7—N2	123.8 (3)	C10—C14—H14B	109.1
O1—C7—C2	130.1 (4)	H14A—C14—H14B	107.9
N2—C7—C2	106.1 (3)