6-(3-Iodo­propyl)­benzo­[f][1,7]­naphthyridin-6-ium iodide

In the title compound, C₁₅H₁₄IN₂⁺·I⁻, the C₁₅H₁₄IN₂⁺ cations and I⁻ anions are joined together via strong C—H...I hydrogen bonds. In the [010] direction, these cations form positively charged columns, between which the I⁻ anions are included.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.043
• wR factor = 0.095
• Data-to-parameter ratio = 21.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: DARCH Package (Burevestnik, 1991); cell refinement: DARCH Package; data reduction: DARCH package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON (Spek,2000); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C15H14IN2^+·I^−	F(000) = 896
Mr = 475.8	Dx = 2.000 Mg m^−3
Monoclinic, P21/c	Melting point = 173–174 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 10.896 (1) Å	Cell parameters from 27 reflections
b = 12.547 (2) Å	θ = 3–22°
c = 13.454 (2) Å	µ = 3.97 mm^−1
β = 120.71 (2)°	T = 293 K
V = 1581.4 (5) Å^3	Tablet, clear pale yellow
Z = 4	0.29 × 0.15 × 0.09 mm

Data collection

DARCH-1 diffractometer	3075 reflections with I > 2σ(I)
Radiation source: BSW x-ray tube	Rint = 0.050
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
ω–2θ scans	h = −14→12
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	k = −16→16
Tmin = 0.491, Tmax = 0.702	l = 0→17
3784 measured reflections	3 standard reflections every 100 reflections
3622 independent reflections	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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 1.109P] where P = (Fo^2 + 2Fc^2)/3
3622 reflections	(Δ/σ)max = 0.012
172 parameters	Δρmax = 1.36 e Å^−3
0 restraints	Δρmin = −1.34 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
I1	0.34454 (4)	0.44544 (3)	0.27367 (3)	0.05835 (12)
I2	0.61764 (4)	0.09761 (4)	0.45654 (3)	0.06918 (15)
N1	0.2450 (5)	0.3524 (3)	0.5084 (4)	0.0534 (10)
N2	0.1508 (5)	0.6291 (4)	0.4363 (3)	0.0592 (12)
C1	0.2646 (7)	0.4620 (4)	0.5067 (5)	0.0548 (13)
H1	0.3532	0.4952	0.5477	0.096 (9)*
C2	0.1389 (6)	0.5158 (4)	0.4378 (4)	0.0491 (12)
C3	0.0242 (7)	0.6907 (4)	0.3579 (5)	0.0655 (15)
H3	0.0346	0.7634	0.3512	0.096 (9)*
C4	−0.1033 (7)	0.6490 (5)	0.2964 (5)	0.0627 (14)
H4	−0.1834	0.6885	0.2457	0.096 (9)*
C5	−0.1075 (7)	0.5437 (4)	0.3133 (5)	0.0549 (12)
H5	−0.1982	0.5135	0.2779	0.096 (9)*
C6	0.0069 (6)	0.4728 (4)	0.3775 (5)	0.0514 (13)
C7	0.0013 (7)	0.3605 (4)	0.3890 (5)	0.0538 (13)
C8	−0.1307 (7)	0.3133 (4)	0.3265 (5)	0.0523 (12)
H8	−0.2112	0.3562	0.2872	0.096 (9)*
C9	−0.1460 (7)	0.2090 (4)	0.3209 (5)	0.0564 (13)
H9	−0.2334	0.1789	0.2680	0.096 (9)*
C10	−0.0314 (7)	0.1435 (4)	0.3944 (5)	0.0594 (14)
H10	−0.0477	0.0707	0.3945	0.096 (9)*
C11	0.1132 (5)	0.1837 (4)	0.4711 (3)	0.0523 (13)
H11	0.1907	0.1433	0.5243	0.096 (9)*
C12	0.1155 (7)	0.2958 (5)	0.4509 (5)	0.0566 (13)
C13	0.3911 (6)	0.2913 (4)	0.5803 (5)	0.087 (2)
H13A	0.4663	0.3428	0.6236	0.18 (2)*
H13B	0.3855	0.2450	0.6357	0.18 (2)*
C14	0.4316 (7)	0.2239 (6)	0.5060 (6)	0.0767 (19)
H14A	0.3574	0.1714	0.4637	0.18 (2)*
H14B	0.4361	0.2698	0.4499	0.18 (2)*
C15	0.5701 (6)	0.1683 (6)	0.5746 (5)	0.0759 (19)
H15A	0.5636	0.1143	0.6233	0.18 (2)*
H15B	0.6443	0.2186	0.6236	0.18 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0659 (2)	0.0649 (2)	0.0599 (2)	0.00025 (16)	0.04346 (19)	−0.00008 (17)
I2	0.0508 (2)	0.0782 (3)	0.0472 (2)	0.02681 (18)	0.00232 (16)	0.00022 (18)
N1	0.079 (3)	0.048 (2)	0.049 (2)	0.002 (2)	0.044 (2)	0.0045 (19)
N2	0.093 (4)	0.047 (2)	0.057 (3)	−0.002 (2)	0.052 (3)	0.004 (2)
C1	0.082 (4)	0.051 (3)	0.055 (3)	0.001 (3)	0.053 (3)	0.001 (2)
C2	0.081 (4)	0.044 (2)	0.059 (3)	0.010 (2)	0.063 (3)	0.002 (2)
C3	0.082 (4)	0.038 (3)	0.062 (3)	0.002 (3)	0.027 (3)	−0.002 (2)
C4	0.084 (4)	0.050 (3)	0.054 (3)	−0.006 (3)	0.036 (3)	−0.005 (3)
C5	0.074 (3)	0.051 (3)	0.052 (3)	−0.003 (2)	0.041 (3)	0.003 (2)
C6	0.081 (4)	0.047 (3)	0.063 (3)	0.009 (2)	0.063 (3)	0.002 (2)
C7	0.088 (4)	0.049 (3)	0.059 (3)	0.006 (3)	0.062 (3)	0.004 (2)
C8	0.082 (4)	0.046 (3)	0.060 (3)	0.008 (2)	0.059 (3)	0.005 (2)
C9	0.085 (4)	0.055 (3)	0.059 (3)	−0.011 (3)	0.058 (3)	−0.008 (2)
C10	0.084 (4)	0.048 (3)	0.050 (3)	−0.004 (3)	0.036 (3)	−0.005 (2)
C11	0.093 (4)	0.041 (2)	0.064 (3)	0.011 (2)	0.070 (3)	0.006 (2)
C12	0.079 (4)	0.057 (3)	0.064 (3)	0.003 (3)	0.058 (3)	0.000 (3)
C13	0.073 (4)	0.106 (5)	0.057 (4)	0.039 (4)	0.016 (3)	0.012 (4)
C14	0.056 (3)	0.085 (5)	0.052 (3)	0.023 (3)	0.001 (3)	0.002 (3)
C15	0.052 (3)	0.105 (5)	0.041 (3)	0.023 (3)	0.002 (2)	0.000 (3)

Geometric parameters (Å, º)

I2—C15	2.102 (7)	C7—C8	1.375 (8)
N1—C1	1.394 (6)	C8—C9	1.316 (7)
N1—C12	1.407 (7)	C8—H8	0.9300
N1—C13	1.577 (5)	C9—C10	1.397 (8)
N2—C2	1.429 (6)	C9—H9	0.9300
N2—C3	1.458 (6)	C10—C11	1.463 (6)
C1—C2	1.376 (8)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.435 (5)
C2—C6	1.352 (8)	C11—H11	0.9300
C3—C4	1.310 (9)	C13—C14	1.537 (7)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.346 (8)	C13—H13B	0.9700
C4—H4	0.9300	C14—C15	1.481 (8)
C5—C6	1.411 (8)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C6—C7	1.422 (7)	C15—H15A	0.9700
C7—C12	1.357 (7)	C15—H15B	0.9700
C1—N1—C12	127.4 (5)	C8—C9—H9	119.9
C1—N1—C13	112.0 (4)	C10—C9—H9	119.9
C12—N1—C13	120.5 (3)	C9—C10—C11	123.2 (5)
C2—N2—C3	118.6 (4)	C9—C10—H10	118.4
C2—C1—N1	112.7 (5)	C11—C10—H10	118.4
C2—C1—H1	123.6	C12—C11—C10	108.7 (4)
N1—C1—H1	123.6	C12—C11—H11	125.6
C6—C2—C1	126.7 (5)	C10—C11—H11	125.6
C6—C2—N2	117.7 (4)	C7—C12—N1	112.6 (3)
C1—C2—N2	115.5 (5)	C7—C12—C11	127.1 (5)
C4—C3—N2	123.5 (5)	N1—C12—C11	120.0 (4)
C4—C3—H3	118.3	C14—C13—N1	113.8 (3)
N2—C3—H3	118.3	C14—C13—H13A	108.8
C3—C4—C5	113.7 (6)	N1—C13—H13A	108.8
C3—C4—H4	123.1	C14—C13—H13B	108.8
C5—C4—H4	123.1	N1—C13—H13B	108.8
C4—C5—C6	128.8 (6)	H13A—C13—H13B	107.7
C4—C5—H5	115.6	C15—C14—C13	113.1 (5)
C6—C5—H5	115.6	C15—C14—H14A	108.9
C2—C6—C5	116.9 (5)	C13—C14—H14A	108.9
C2—C6—C7	114.9 (5)	C15—C14—H14B	108.9
C5—C6—C7	128.2 (6)	C13—C14—H14B	108.9
C12—C7—C8	117.6 (5)	H14A—C14—H14B	107.8
C12—C7—C6	125.6 (5)	C14—C15—I2	107.1 (4)
C8—C7—C6	116.7 (5)	C14—C15—H15A	110.3
C9—C8—C7	121.7 (6)	I2—C15—H15A	110.3
C9—C8—H8	119.2	C14—C15—H15B	110.3
C7—C8—H8	119.2	I2—C15—H15B	110.3
C8—C9—C10	120.2 (6)	H15A—C15—H15B	108.6
C12—N1—C1—C2	−1.2 (7)	C12—C7—C8—C9	−3.8 (7)
C13—N1—C1—C2	175.9 (3)	C6—C7—C8—C9	172.5 (4)
N1—C1—C2—C6	1.1 (6)	C7—C8—C9—C10	11.1 (7)
N1—C1—C2—N2	177.4 (4)	C8—C9—C10—C11	−6.8 (8)
C3—N2—C2—C6	−8.4 (6)	C9—C10—C11—C12	−3.9 (7)
C3—N2—C2—C1	174.9 (5)	C8—C7—C12—N1	178.2 (4)
C2—N2—C3—C4	6.7 (9)	C6—C7—C12—N1	2.2 (7)
N2—C3—C4—C5	0.9 (9)	C8—C7—C12—C11	−8.7 (7)
C3—C4—C5—C6	−7.3 (9)	C6—C7—C12—C11	175.2 (4)
C1—C2—C6—C5	179.3 (4)	C1—N1—C12—C7	−0.3 (7)
N2—C2—C6—C5	3.1 (6)	C13—N1—C12—C7	−177.1 (3)
C1—C2—C6—C7	0.5 (6)	C1—N1—C12—C11	−174.0 (4)
N2—C2—C6—C7	−175.8 (4)	C13—N1—C12—C11	9.2 (6)
C4—C5—C6—C2	5.4 (8)	C10—C11—C12—C7	11.8 (7)
C4—C5—C6—C7	−175.9 (5)	C10—C11—C12—N1	−175.5 (4)
C2—C6—C7—C12	−2.3 (7)	C1—N1—C13—C14	−109.5 (4)
C5—C6—C7—C12	179.0 (5)	C12—N1—C13—C14	67.7 (5)
C2—C6—C7—C8	−178.3 (4)	N1—C13—C14—C15	179.1 (5)
C5—C6—C7—C8	3.0 (7)	C13—C14—C15—I2	−172.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···I1^i	0.93	3.02	3.919 (7)	164
C11—H11···I1^ii	0.93	3.09	3.882 (4)	144
C13—H13B···I1^ii	0.97	3.19	4.147 (5)	167
C14—H14B···I1	0.97	3.01	3.920 (7)	157

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