2,6-Dibromo­phenyl acridine-9-carboxyl­ate

Sikorski, A.; Krzymiński, K.; Konitz, A.; Błażejowski, J.

doi:10.1107/S1600536805027145

2,6-Dibromophenyl acridine-9-carboxylate

A. Sikorski, K. Krzymiński, A. Konitz and J. Błażejowski

Adjacent molecules of the title compound, C₂₀H₁₁Br₂NO₂, are oriented either parallel or antiparallel; in the latter case, there are four intermolecular π–π interactions between acridine rings. The acridine and benzene ring systems are inclined at an angle of 41.2 (2)° to each other. There is also a short intermolecular Br

Br contact.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027145/er6021sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027145/er6021Isup2.hkl Contains datablock I

CCDC reference: 287554

checkCIF report

Key indicators

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.005 Å
R factor = 0.028
wR factor = 0.081
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br24   ..  Br24    ..       3.54 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Phenyl acridine-9-carboxylates have become interesting chemiluminescent agents, since they can be oxidized by H₂O₂, persulfates, peroxides or other oxidants to electronically excited 9-acridinones (Dodeigne et al., 2000; Razawi & McCapra, 2000), which are known to be efficient light emitters (Boużyk et al., 2003). For this reason, these compounds are widely applied as chemiluminescent indicators, or fragments of chemiluminescent labels, in immunological, medical, environmental and biochemical analyses (Dodeigne et al., 2000). Continuing the search for new, analytically useful chemiluminogens, we synthesized dibromophenyl acridine-9-carboxylate in order to find out how the presence of the Br atoms affects the stability and chemiluminogenic properties of this group of compounds. This paper, together with our earlier publications on the crystallography of phenyl acridine-9-carboxylates (Meszko et al., 2002; Sikorski et al., 2005a,b), thus extends the prospects of finding further chemiluminogens with interesting practical applications.

Bond lengths and angles may be regarded as typical for acridine-based derivatives (Table 1).

The acridine and phenyl groups are planar, with average deviations of 0.012 (3) and 0.005 (3) Å, respectively. The least-squares planes (defined by all non-H atoms) of the acridine and phenyl groups are inclined at an angle of 41.2 (2)° to each other (Fig. 1).

The angle between the least-squares planes of the acridine group and the carboxyl group, defined by atoms C16, O16 and O17, is 51.0 (3)°. Adjacent molecules are oriented either parallel or antiparallel. In the latter case, there are four intermolecular π–π interactions involving the acridine rings (Fig. 2 and Table 2). In addition, there is a short intermolecular Br···Br contact [Br24···Br24(2 − x, −1 − y, 1 − z) = 3.54 (1) Å].

Experimental top

The title compound was synthesized by heating commercially available acridine-9-carboxylic acid with excess thionyl chloride. The product of this reaction, the acid chloride, was reacted with 2,6-dibromophenol (Sato, 1996). The synthesis was carried out in dichloromethane in the presence of triethylamine and catalytic amounts of 4-dimethylaminopyridine. [Please give quantities of reagents, reaction conditions etc.] The crude product was purified chromatographically (SiO₂, n-hexane/ethyl acetate, 3:2 v/v). Yellow crystals suitable for X-ray analysis were grown from cyclohexane (m.p. 428–429 K).

Computing details top

Data collection: KM-4 Software (Kuma, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and 25% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The arrangement of the molecules of the title compound in the unit cell, viewed along the a axis. The π–π interactions are represented by dashed lines [symmetry codes: (i) 2 − x, 1 − y, −z; (ii) 2 − x, −y, −z] and Br···Br contacts by dotted lines [symmetry code: (iii) 2 − x, −1 − y, 1 − z.]. H atoms have been omitted.

2,6-Dibromophenyl acridine-9-carboxylate top

Crystal data top

C₂₀H₁₁Br₂NO₂	Z = 2
M_r = 457.12	F(000) = 448
Triclinic, P1	D_x = 1.813 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.385 (2) Å	Cell parameters from 50 reflections
b = 9.840 (2) Å	θ = 2.5–25.0°
c = 11.246 (2) Å	µ = 4.85 mm⁻¹
α = 66.22 (3)°	T = 290 K
β = 77.23 (3)°	Prism, yellow
γ = 61.85 (3)°	0.5 × 0.4 × 0.3 mm
V = 837.4 (4) Å³

Data collection top

Kuma KM-4 diffractometer	1803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ω/2θ scans	h = −10→11
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.112, T_max = 0.233	l = 0→13
3074 measured reflections	3 standard reflections every 200 reflections
2909 independent reflections	intensity decay: 0.4%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0616P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max < 0.001
2909 reflections	Δρ_max = 0.36 e Å⁻³
227 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (11)

Crystal data top

C₂₀H₁₁Br₂NO₂	γ = 61.85 (3)°
M_r = 457.12	V = 837.4 (4) Å³
Triclinic, P1	Z = 2
a = 9.385 (2) Å	Mo Kα radiation
b = 9.840 (2) Å	µ = 4.85 mm⁻¹
c = 11.246 (2) Å	T = 290 K
α = 66.22 (3)°	0.5 × 0.4 × 0.3 mm
β = 77.23 (3)°

Data collection top

Kuma KM-4 diffractometer	1803 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.034
T_min = 0.112, T_max = 0.233	3 standard reflections every 200 reflections
3074 measured reflections	intensity decay: 0.4%
2909 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 0.85	Δρ_max = 0.36 e Å⁻³
2909 reflections	Δρ_min = −0.33 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.8165 (4)	0.3693 (4)	0.0252 (3)	0.0446 (9)
H1	0.7268	0.3676	0.0801	0.054*
C2	0.8062 (5)	0.5101 (4)	−0.0703 (3)	0.0516 (10)
H2	0.7091	0.6041	−0.0805	0.062*
C3	0.9382 (5)	0.5188 (5)	−0.1551 (4)	0.0548 (10)
H3	0.9287	0.6181	−0.2198	0.066*
C4	1.0791 (5)	0.3830 (5)	−0.1428 (3)	0.0494 (10)
H4	1.1658	0.3890	−0.2003	0.059*
C5	1.4138 (4)	−0.1775 (5)	0.0639 (4)	0.0505 (10)
H5	1.4971	−0.1622	0.0061	0.061*
C6	1.4402 (4)	−0.3276 (5)	0.1523 (4)	0.0527 (10)
H6	1.5416	−0.4150	0.1556	0.063*
C7	1.3136 (5)	−0.3527 (4)	0.2406 (4)	0.0499 (9)
H7	1.3321	−0.4577	0.2992	0.060*
C8	1.1682 (4)	−0.2281 (4)	0.2408 (3)	0.0406 (8)
H8	1.0881	−0.2474	0.3009	0.049*
C9	0.9866 (4)	0.0716 (4)	0.1431 (3)	0.0339 (7)
N10	1.2415 (3)	0.1024 (4)	−0.0353 (3)	0.0439 (7)
C11	0.9627 (4)	0.2226 (4)	0.0439 (3)	0.0356 (7)
C12	1.0968 (4)	0.2310 (4)	−0.0432 (3)	0.0394 (8)
C13	1.1341 (4)	−0.0655 (4)	0.1502 (3)	0.0351 (7)
C14	1.2605 (4)	−0.0425 (4)	0.0579 (3)	0.0401 (8)
C15	0.8517 (4)	0.0640 (4)	0.2410 (3)	0.0351 (8)
O16	0.9044 (3)	−0.0041 (3)	0.3649 (2)	0.0374 (5)
O17	0.7146 (3)	0.1154 (3)	0.2191 (2)	0.0531 (7)
C18	0.7849 (4)	0.0068 (4)	0.4638 (3)	0.0346 (8)
C19	0.7399 (4)	−0.1203 (4)	0.5313 (3)	0.0358 (8)
C20	0.6281 (4)	−0.1116 (5)	0.6333 (3)	0.0435 (9)
H20	0.5984	−0.1976	0.6781	0.052*
C21	0.5603 (4)	0.0257 (5)	0.6688 (3)	0.0469 (9)
H21	0.4860	0.0311	0.7388	0.056*
C22	0.6012 (4)	0.1542 (5)	0.6020 (3)	0.0448 (9)
H22	0.5537	0.2473	0.6254	0.054*
C23	0.7139 (4)	0.1443 (4)	0.4992 (3)	0.0395 (8)
Br24	0.83211 (5)	−0.30774 (4)	0.48304 (4)	0.05415 (16)
Br25	0.77029 (5)	0.32050 (5)	0.40609 (4)	0.05659 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.050 (2)	0.046 (2)	0.034 (2)	−0.0199 (18)	0.0022 (17)	−0.0136 (18)
C2	0.058 (3)	0.046 (2)	0.041 (2)	−0.0160 (19)	−0.0039 (18)	−0.0119 (18)
C3	0.077 (3)	0.047 (2)	0.038 (2)	−0.034 (2)	−0.007 (2)	−0.0006 (17)
C4	0.060 (3)	0.060 (2)	0.034 (2)	−0.040 (2)	0.0031 (17)	−0.0074 (18)
C5	0.042 (2)	0.059 (2)	0.051 (2)	−0.0230 (19)	0.0138 (17)	−0.027 (2)
C6	0.042 (2)	0.054 (2)	0.053 (2)	−0.0101 (18)	0.0038 (18)	−0.025 (2)
C7	0.057 (2)	0.040 (2)	0.047 (2)	−0.0196 (19)	0.0026 (18)	−0.0138 (17)
C8	0.048 (2)	0.0409 (19)	0.0343 (19)	−0.0229 (17)	0.0062 (16)	−0.0142 (15)
C9	0.0397 (19)	0.0426 (19)	0.0259 (17)	−0.0243 (16)	0.0028 (14)	−0.0121 (15)
N10	0.0405 (17)	0.0547 (19)	0.0351 (17)	−0.0257 (15)	0.0100 (13)	−0.0138 (15)
C11	0.0426 (18)	0.0445 (19)	0.0254 (16)	−0.0234 (15)	0.0012 (14)	−0.0133 (15)
C12	0.050 (2)	0.052 (2)	0.0263 (17)	−0.0332 (18)	0.0040 (15)	−0.0120 (16)
C13	0.0389 (19)	0.0427 (19)	0.0299 (18)	−0.0221 (16)	0.0019 (14)	−0.0145 (15)
C14	0.0379 (19)	0.053 (2)	0.038 (2)	−0.0246 (17)	0.0065 (15)	−0.0223 (18)
C15	0.040 (2)	0.0394 (18)	0.0269 (18)	−0.0209 (16)	0.0024 (14)	−0.0096 (14)
O16	0.0305 (12)	0.0459 (13)	0.0282 (12)	−0.0157 (10)	0.0055 (10)	−0.0101 (10)
O17	0.0420 (15)	0.0836 (19)	0.0352 (14)	−0.0363 (14)	0.0005 (11)	−0.0119 (13)
C18	0.0318 (18)	0.0436 (19)	0.0254 (18)	−0.0166 (15)	0.0010 (14)	−0.0098 (15)
C19	0.0327 (18)	0.0369 (18)	0.0301 (18)	−0.0133 (14)	−0.0044 (14)	−0.0047 (14)
C20	0.039 (2)	0.052 (2)	0.0326 (19)	−0.0252 (17)	0.0038 (15)	−0.0046 (16)
C21	0.038 (2)	0.068 (3)	0.0320 (19)	−0.0246 (19)	0.0077 (16)	−0.0171 (18)
C22	0.042 (2)	0.056 (2)	0.040 (2)	−0.0206 (17)	0.0058 (16)	−0.0256 (18)
C23	0.0421 (19)	0.0445 (19)	0.0320 (18)	−0.0239 (16)	0.0039 (15)	−0.0098 (15)
Br24	0.0545 (3)	0.0409 (2)	0.0616 (3)	−0.02163 (18)	0.00636 (19)	−0.01567 (18)
Br25	0.0730 (3)	0.0515 (2)	0.0502 (3)	−0.0379 (2)	0.0072 (2)	−0.01362 (19)

Geometric parameters (Å, º) top

C1—C2	1.343 (5)	C9—C15	1.493 (4)
C1—C11	1.422 (5)	N10—C12	1.339 (5)
C1—H1	0.9300	N10—C14	1.342 (4)
C2—C3	1.402 (5)	C11—C12	1.428 (5)
C2—H2	0.9300	C13—C14	1.433 (4)
C3—C4	1.348 (5)	C15—O16	1.369 (4)
C3—H3	0.9300	C15—O17	1.182 (4)
C4—C12	1.420 (5)	O16—C18	1.393 (3)
C4—H4	0.9300	C18—C23	1.378 (5)
C5—C6	1.345 (5)	C18—C19	1.382 (5)
C5—C14	1.416 (5)	C19—C20	1.373 (4)
C5—H5	0.9300	C19—Br24	1.881 (3)
C6—C7	1.420 (5)	C20—C21	1.379 (5)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.336 (5)	C21—C22	1.369 (5)
C7—H7	0.9300	C21—H21	0.9300
C8—C13	1.431 (5)	C22—C23	1.385 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C13	1.394 (5)	C23—Br25	1.882 (3)
C9—C11	1.401 (5)

C2—C1—C11	121.0 (3)	N10—C12—C4	117.4 (3)
C2—C1—H1	119.5	N10—C12—C11	123.4 (3)
C11—C1—H1	119.5	C4—C12—C11	119.2 (3)
C1—C2—C3	121.6 (4)	C9—C13—C8	125.1 (3)
C1—C2—H2	119.2	C9—C13—C14	117.5 (3)
C3—C2—H2	119.2	C8—C13—C14	117.4 (3)
C4—C3—C2	119.9 (3)	N10—C14—C5	117.5 (3)
C4—C3—H3	120.0	N10—C14—C13	123.1 (3)
C2—C3—H3	120.0	C5—C14—C13	119.4 (3)
C3—C4—C12	120.8 (3)	C9—C15—O16	111.0 (3)
C3—C4—H4	119.6	C9—C15—O17	126.6 (3)
C12—C4—H4	119.6	C15—O16—C18	116.1 (2)
C6—C5—C14	120.8 (3)	O16—C15—O17	122.4 (3)
C6—C5—H5	119.6	C23—C18—C19	118.9 (3)
C14—C5—H5	119.6	C23—C18—O16	119.6 (3)
C5—C6—C7	120.1 (3)	C19—C18—O16	121.4 (3)
C5—C6—H6	119.9	C20—C19—C18	120.8 (3)
C7—C6—H6	119.9	C20—C19—Br24	119.4 (3)
C8—C7—C6	121.2 (3)	C18—C19—Br24	119.8 (2)
C8—C7—H7	119.4	C19—C20—C21	119.5 (3)
C6—C7—H7	119.4	C19—C20—H20	120.2
C7—C8—C13	121.0 (3)	C21—C20—H20	120.2
C7—C8—H8	119.5	C22—C21—C20	120.7 (3)
C13—C8—H8	119.5	C22—C21—H21	119.7
C13—C9—C11	120.2 (3)	C20—C21—H21	119.7
C13—C9—C15	121.7 (3)	C21—C22—C23	119.4 (3)
C11—C9—C15	118.1 (3)	C21—C22—H22	120.3
C12—N10—C14	118.3 (3)	C23—C22—H22	120.3
C9—C11—C1	125.1 (3)	C18—C23—C22	120.7 (3)
C9—C11—C12	117.4 (3)	C18—C23—Br25	119.5 (2)
C1—C11—C12	117.5 (3)	C22—C23—Br25	119.8 (3)

C11—C1—C2—C3	−0.2 (6)	C6—C5—C14—N10	−178.0 (4)
C1—C2—C3—C4	1.0 (6)	C6—C5—C14—C13	2.2 (6)
C2—C3—C4—C12	−1.2 (6)	C9—C13—C14—N10	−1.5 (5)
C14—C5—C6—C7	0.4 (6)	C8—C13—C14—N10	177.3 (3)
C5—C6—C7—C8	−2.3 (6)	C9—C13—C14—C5	178.2 (3)
C6—C7—C8—C13	1.4 (6)	C8—C13—C14—C5	−3.0 (5)
C13—C9—C11—C1	178.5 (3)	C13—C9—C15—O17	−132.9 (4)
C15—C9—C11—C1	−2.9 (5)	C15—O16—C18—C23	−87.1 (4)
C13—C9—C11—C12	−3.2 (5)	C13—C9—C15—O16	50.6 (4)
C15—C9—C11—C12	175.4 (3)	C11—C9—C15—O16	−128.1 (3)
C2—C1—C11—C9	177.9 (4)	O17—C15—O16—C18	−6.9 (5)
C2—C1—C11—C12	−0.4 (5)	C9—C15—O16—C18	169.8 (3)
C14—N10—C12—C4	−179.7 (3)	C11—C9—C15—O17	48.4 (5)
C14—N10—C12—C11	1.3 (5)	C15—O16—C18—C19	95.5 (3)
C3—C4—C12—N10	−178.5 (3)	C23—C18—C19—C20	−1.0 (5)
C3—C4—C12—C11	0.6 (5)	O16—C18—C19—C20	176.5 (3)
C9—C11—C12—N10	0.8 (5)	C23—C18—C19—Br24	178.9 (2)
C1—C11—C12—N10	179.2 (3)	O16—C18—C19—Br24	−3.6 (4)
C9—C11—C12—C4	−178.2 (3)	C18—C19—C20—C21	−0.1 (5)
C1—C11—C12—C4	0.2 (5)	Br24—C19—C20—C21	−180.0 (3)
C11—C9—C13—C8	−175.1 (3)	C19—C20—C21—C22	1.1 (5)
C15—C9—C13—C8	6.3 (5)	C20—C21—C22—C23	−1.1 (5)
C11—C9—C13—C14	3.6 (5)	C19—C18—C23—C22	1.0 (5)
C15—C9—C13—C14	−175.1 (3)	O16—C18—C23—C22	−176.5 (3)
C7—C8—C13—C9	179.9 (3)	C19—C18—C23—Br25	−178.6 (2)
C7—C8—C13—C14	1.3 (5)	O16—C18—C23—Br25	3.9 (4)
C12—N10—C14—C5	179.4 (3)	C21—C22—C23—C18	0.0 (5)
C12—N10—C14—C13	−0.9 (5)	C21—C22—C23—Br25	179.7 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₁Br₂NO₂
M_r	457.12
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	9.385 (2), 9.840 (2), 11.246 (2)
α, β, γ (°)	66.22 (3), 77.23 (3), 61.85 (3)
V (Å³)	837.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.85
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Kuma KM-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.112, 0.233
No. of measured, independent and observed [I > 2σ(I)] reflections	3074, 2909, 1803
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.081, 0.85
No. of reflections	2909
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

Computer programs: KM-4 Software (Kuma, 1989), KM-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

C9—C11	1.401 (5)	C15—O17	1.182 (4)
C9—C15	1.493 (4)	O16—C18	1.393 (3)
N10—C12	1.339 (5)	C18—C19	1.382 (5)
C15—O16	1.369 (4)	C19—Br24	1.881 (3)

C9—C15—O16	111.0 (3)	C15—O16—C18	116.1 (2)
C9—C15—O17	126.6 (3)	O16—C15—O17	122.4 (3)

C9—C15—O16—C18	169.8 (3)	C15—O16—C18—C19	95.5 (3)
C11—C9—C15—O17	48.4 (5)	O16—C18—C19—Br24	−3.6 (4)

π–π interactions (Å, °) in the title compound. top

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar dist.	Offset
1	1ⁱ	3.880 (2)	0.0	3.590 (3)	1.472 (2)
2	2ⁱⁱ	3.766 (2)	0.0	3.491 (3)	1.413 (2)
2	3ⁱ	3.890 (2)	2.0	3.479 (3)	1.740 (2)
3	2ⁱ	3.890 (2)	2.0	3.530 (3)	1.634 (2)

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

Notes: Cg represents the centre of gravity of the rings, as follows: Cg1, ring C9/C11/C12/N10/C14/C13; Cg2, ring C1/C2/C3/C4/C12/C11; Cg3, ring C5/C6/C7/C8/C13/C14. Cg···Cg is the distance between ring centroids. The dihedral angle is that between the planes of CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. Offset is the perpendicular distance of ring I from ring J.

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2,6-Dibromo­phenyl acridine-9-carboxyl­ate

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2,6-Dibromophenyl acridine-9-carboxylate