9-Benzamido-acridinium chloride.

In the title compound, C(20)H(15)N(2)O(+)·Cl(-), the dihedral angle between the fused-ring system and the benzene ring is 63.10 (7)°. In the crystal, N-H⋯Cl hydrogen bonds link the components and aromatic π-π stacking [shortest centroid-centroid distance = 3.6421 (12) Å] occurs.

Related literature

For background to acridine derivatives, see: Antonini (2002 ▶); Carvalho et al. (2005 ▶). For the synthesis, see: He et al. (2008 ▶); Chandregowda et al. (2009 ▶). For related structures, see: Sikorski et al. (2007 ▶, 2008 ▶); Trzybiníski et al. (2009 ▶).

Experimental

Crystal data

C20H15N2O+·Cl−

M = 334.79

Triclinic,

a = 8.9601 (17) Å

b = 9.0084 (17) Å

c = 10.8775 (18) Å

α = 79.168 (7)°

β = 65.855 (5)°

γ = 86.927 (7)°

V = 786.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 93 K

0.37 × 0.33 × 0.17 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.959

4772 measured reflections

2955 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.069

S = 1.00

2955 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039439/hb5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039439/hb5083Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H15N2O+·Cl−	Z = 2
Mr = 334.79	F(000) = 348
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9601 (17) Å	Cell parameters from 2420 reflections
b = 9.0084 (17) Å	θ = 3.2–27.5°
c = 10.8775 (18) Å	µ = 0.25 mm−1
α = 79.168 (7)°	T = 93 K
β = 65.855 (5)°	Chunk, yellow
γ = 86.927 (7)°	0.37 × 0.33 × 0.17 mm
V = 786.6 (2) Å3

Rigaku SPIDER diffractometer	2955 independent reflections
Radiation source: Rotating Anode	2538 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
Tmin = 0.913, Tmax = 0.959	k = −10→11
4772 measured reflections	l = −12→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0136P)2 + 0.516P] where P = (Fo2 + 2Fc2)/3
2955 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.78153 (5)	0.85506 (5)	−0.03376 (4)	0.01909 (12)
O1	0.39684 (14)	0.63975 (13)	0.49853 (12)	0.0187 (3)
N1	0.34182 (17)	0.35116 (16)	0.16256 (14)	0.0143 (3)
N2	0.54610 (18)	0.68607 (16)	0.26770 (15)	0.0153 (3)
C1	0.5768 (2)	0.46569 (18)	0.16353 (17)	0.0139 (4)
C2	0.7475 (2)	0.45912 (19)	0.13000 (17)	0.0161 (4)
H2	0.7988	0.5317	0.1541	0.019*
C3	0.8384 (2)	0.34982 (19)	0.06364 (18)	0.0178 (4)
H3	0.9524	0.3469	0.0422	0.021*
C4	0.7652 (2)	0.2403 (2)	0.02605 (18)	0.0185 (4)
H4	0.8306	0.1652	−0.0205	0.022*
C5	0.6021 (2)	0.24183 (19)	0.05601 (17)	0.0165 (4)
H5	0.5538	0.1687	0.0301	0.020*
C6	0.5053 (2)	0.35355 (18)	0.12623 (17)	0.0142 (4)
C7	0.2393 (2)	0.44990 (18)	0.23448 (17)	0.0140 (4)
C8	0.0696 (2)	0.4369 (2)	0.27045 (18)	0.0176 (4)
H8	0.0268	0.3567	0.2478	0.021*
C9	−0.0322 (2)	0.5401 (2)	0.33778 (18)	0.0194 (4)
H9	−0.1468	0.5297	0.3649	0.023*
C10	0.0313 (2)	0.6631 (2)	0.36779 (18)	0.0197 (4)
H10	−0.0406	0.7372	0.4106	0.024*
C11	0.1935 (2)	0.67615 (19)	0.33612 (18)	0.0172 (4)
H11	0.2338	0.7592	0.3571	0.021*
C12	0.3043 (2)	0.56678 (18)	0.27180 (17)	0.0141 (4)
C13	0.4735 (2)	0.57227 (18)	0.23643 (17)	0.0139 (4)
C14	0.5083 (2)	0.70877 (18)	0.39917 (18)	0.0145 (4)
C15	0.6172 (2)	0.82148 (18)	0.41153 (17)	0.0139 (4)
C16	0.7367 (2)	0.91166 (19)	0.30042 (18)	0.0175 (4)
H16	0.7528	0.9047	0.2098	0.021*
C17	0.8326 (2)	1.01193 (19)	0.32150 (19)	0.0198 (4)
H17	0.9140	1.0735	0.2453	0.024*
C18	0.8099 (2)	1.02228 (19)	0.45330 (19)	0.0187 (4)
H18	0.8765	1.0902	0.4674	0.022*
C19	0.6903 (2)	0.93372 (19)	0.56455 (19)	0.0190 (4)
H19	0.6746	0.9412	0.6550	0.023*
C20	0.5936 (2)	0.83416 (19)	0.54403 (18)	0.0165 (4)
H20	0.5109	0.7743	0.6206	0.020*
H1N	0.298 (2)	0.278 (2)	0.1340 (19)	0.023 (5)*
H2N	0.633 (2)	0.736 (2)	0.197 (2)	0.024 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0200 (2)	0.0198 (2)	0.0173 (2)	−0.00404 (17)	−0.00573 (19)	−0.00612 (18)
O1	0.0190 (7)	0.0196 (6)	0.0160 (7)	−0.0045 (5)	−0.0056 (6)	−0.0020 (5)
N1	0.0175 (8)	0.0134 (7)	0.0137 (8)	−0.0022 (6)	−0.0077 (6)	−0.0023 (6)
N2	0.0160 (8)	0.0165 (8)	0.0128 (8)	−0.0038 (6)	−0.0040 (7)	−0.0045 (6)
C1	0.0177 (9)	0.0131 (8)	0.0103 (9)	−0.0006 (7)	−0.0060 (7)	−0.0001 (7)
C2	0.0183 (9)	0.0165 (9)	0.0147 (9)	−0.0034 (7)	−0.0083 (8)	−0.0011 (7)
C3	0.0164 (10)	0.0183 (9)	0.0166 (10)	0.0015 (7)	−0.0058 (8)	−0.0008 (8)
C4	0.0230 (10)	0.0168 (9)	0.0139 (9)	0.0029 (7)	−0.0062 (8)	−0.0027 (7)
C5	0.0228 (10)	0.0141 (9)	0.0143 (9)	−0.0002 (7)	−0.0090 (8)	−0.0029 (7)
C6	0.0175 (10)	0.0143 (8)	0.0102 (9)	−0.0022 (7)	−0.0061 (7)	0.0010 (7)
C7	0.0175 (9)	0.0139 (8)	0.0104 (9)	−0.0008 (7)	−0.0061 (7)	−0.0004 (7)
C8	0.0194 (10)	0.0198 (9)	0.0155 (9)	−0.0030 (7)	−0.0094 (8)	−0.0018 (8)
C9	0.0144 (9)	0.0277 (10)	0.0166 (9)	−0.0007 (8)	−0.0074 (8)	−0.0028 (8)
C10	0.0203 (10)	0.0234 (10)	0.0159 (10)	0.0054 (8)	−0.0077 (8)	−0.0055 (8)
C11	0.0215 (10)	0.0169 (9)	0.0156 (9)	0.0009 (7)	−0.0096 (8)	−0.0039 (8)
C12	0.0170 (9)	0.0143 (8)	0.0109 (9)	−0.0013 (7)	−0.0060 (7)	−0.0007 (7)
C13	0.0188 (10)	0.0126 (8)	0.0101 (8)	−0.0030 (7)	−0.0064 (7)	0.0004 (7)
C14	0.0159 (9)	0.0130 (8)	0.0166 (9)	0.0033 (7)	−0.0085 (8)	−0.0040 (7)
C15	0.0148 (9)	0.0121 (8)	0.0169 (9)	0.0024 (7)	−0.0078 (8)	−0.0045 (7)
C16	0.0202 (10)	0.0186 (9)	0.0150 (9)	−0.0005 (7)	−0.0070 (8)	−0.0058 (8)
C17	0.0201 (10)	0.0181 (9)	0.0187 (10)	−0.0039 (8)	−0.0044 (8)	−0.0042 (8)
C18	0.0200 (10)	0.0164 (9)	0.0238 (10)	0.0003 (7)	−0.0118 (8)	−0.0064 (8)
C19	0.0261 (10)	0.0183 (9)	0.0171 (10)	0.0026 (8)	−0.0123 (8)	−0.0063 (8)
C20	0.0205 (10)	0.0141 (8)	0.0150 (9)	−0.0002 (7)	−0.0077 (8)	−0.0015 (7)

O1—C14	1.218 (2)	C8—H8	0.9500
N1—C6	1.352 (2)	C9—C10	1.419 (2)
N1—C7	1.354 (2)	C9—H9	0.9500
N1—H1N	0.939 (19)	C10—C11	1.356 (2)
N2—C14	1.381 (2)	C10—H10	0.9500
N2—C13	1.405 (2)	C11—C12	1.425 (2)
N2—H2N	0.902 (19)	C11—H11	0.9500
C1—C13	1.414 (2)	C12—C13	1.404 (2)
C1—C2	1.421 (2)	C14—C15	1.505 (2)
C1—C6	1.425 (2)	C15—C16	1.390 (2)
C2—C3	1.362 (2)	C15—C20	1.395 (2)
C2—H2	0.9500	C16—C17	1.389 (2)
C3—C4	1.418 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.384 (2)
C4—C5	1.360 (2)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.385 (2)
C5—C6	1.415 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.387 (2)
C7—C8	1.412 (2)	C19—H19	0.9500
C7—C12	1.426 (2)	C20—H20	0.9500
C8—C9	1.361 (2)
C6—N1—C7	123.57 (14)	C11—C10—C9	120.77 (16)
C6—N1—H1N	117.6 (11)	C11—C10—H10	119.6
C7—N1—H1N	118.8 (11)	C9—C10—H10	119.6
C14—N2—C13	124.05 (15)	C10—C11—C12	120.82 (16)
C14—N2—H2N	120.0 (12)	C10—C11—H11	119.6
C13—N2—H2N	115.3 (12)	C12—C11—H11	119.6
C13—C1—C2	123.94 (15)	C13—C12—C11	124.12 (15)
C13—C1—C6	118.42 (15)	C13—C12—C7	118.46 (15)
C2—C1—C6	117.58 (15)	C11—C12—C7	117.32 (15)
C3—C2—C1	120.64 (16)	C12—C13—N2	121.44 (15)
C3—C2—H2	119.7	C12—C13—C1	120.60 (15)
C1—C2—H2	119.7	N2—C13—C1	117.93 (15)
C2—C3—C4	120.88 (17)	O1—C14—N2	122.22 (15)
C2—C3—H3	119.6	O1—C14—C15	122.34 (15)
C4—C3—H3	119.6	N2—C14—C15	115.42 (15)
C5—C4—C3	120.67 (16)	C16—C15—C20	119.27 (15)
C5—C4—H4	119.7	C16—C15—C14	124.14 (15)
C3—C4—H4	119.7	C20—C15—C14	116.59 (15)
C4—C5—C6	119.29 (16)	C17—C16—C15	120.21 (16)
C4—C5—H5	120.4	C17—C16—H16	119.9
C6—C5—H5	120.4	C15—C16—H16	119.9
N1—C6—C5	119.64 (15)	C18—C17—C16	120.14 (17)
N1—C6—C1	119.40 (15)	C18—C17—H17	119.9
C5—C6—C1	120.93 (16)	C16—C17—H17	119.9
N1—C7—C8	119.67 (15)	C17—C18—C19	120.02 (16)
N1—C7—C12	119.52 (15)	C17—C18—H18	120.0
C8—C7—C12	120.81 (15)	C19—C18—H18	120.0
C9—C8—C7	119.44 (16)	C18—C19—C20	120.04 (16)
C9—C8—H8	120.3	C18—C19—H19	120.0
C7—C8—H8	120.3	C20—C19—H19	120.0
C8—C9—C10	120.61 (17)	C19—C20—C15	120.31 (16)
C8—C9—H9	119.7	C19—C20—H20	119.8
C10—C9—H9	119.7	C15—C20—H20	119.8
C13—C1—C2—C3	177.69 (17)	C8—C7—C12—C11	−5.1 (2)
C6—C1—C2—C3	0.5 (3)	C11—C12—C13—N2	2.5 (3)
C1—C2—C3—C4	0.2 (3)	C7—C12—C13—N2	178.76 (16)
C2—C3—C4—C5	−0.2 (3)	C11—C12—C13—C1	−175.20 (17)
C3—C4—C5—C6	−0.4 (3)	C7—C12—C13—C1	1.0 (2)
C7—N1—C6—C5	177.34 (16)	C14—N2—C13—C12	61.0 (2)
C7—N1—C6—C1	−0.5 (2)	C14—N2—C13—C1	−121.22 (18)
C4—C5—C6—N1	−176.64 (16)	C2—C1—C13—C12	−176.74 (16)
C4—C5—C6—C1	1.2 (3)	C6—C1—C13—C12	0.4 (2)
C13—C1—C6—N1	−0.7 (2)	C2—C1—C13—N2	5.4 (3)
C2—C1—C6—N1	176.61 (16)	C6—C1—C13—N2	−177.42 (15)
C13—C1—C6—C5	−178.53 (16)	C13—N2—C14—O1	−7.0 (3)
C2—C1—C6—C5	−1.2 (2)	C13—N2—C14—C15	171.42 (15)
C6—N1—C7—C8	−178.65 (16)	O1—C14—C15—C16	−174.41 (17)
C6—N1—C7—C12	2.0 (3)	N2—C14—C15—C16	7.1 (2)
N1—C7—C8—C9	−177.30 (17)	O1—C14—C15—C20	5.4 (2)
C12—C7—C8—C9	2.1 (3)	N2—C14—C15—C20	−173.03 (15)
C7—C8—C9—C10	2.2 (3)	C20—C15—C16—C17	0.7 (3)
C8—C9—C10—C11	−3.3 (3)	C14—C15—C16—C17	−179.45 (16)
C9—C10—C11—C12	0.1 (3)	C15—C16—C17—C18	0.2 (3)
C10—C11—C12—C13	−179.75 (17)	C16—C17—C18—C19	−0.7 (3)
C10—C11—C12—C7	4.0 (3)	C17—C18—C19—C20	0.2 (3)
N1—C7—C12—C13	−2.2 (2)	C18—C19—C20—C15	0.6 (3)
C8—C7—C12—C13	178.44 (16)	C16—C15—C20—C19	−1.1 (3)
N1—C7—C12—C11	174.28 (15)	C14—C15—C20—C19	179.04 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1i	0.93 (2)	2.09 (2)	3.0167 (17)	168 (8)
N2—H2N···Cl1	0.90 (2)	2.37 (2)	3.2139 (17)	154 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1i	0.93 (2)	2.09 (2)	3.0167 (17)	168 (8)
N2—H2N⋯Cl1	0.90 (2)	2.37 (2)	3.2139 (17)	154 (4)

Symmetry code: (i) .