Literature DB >> 21579407

9-(4-Bromo-phenoxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

Damian Trzybiński¹, Karol Krzymiński, Artur Sikorski, Jerzy Błażejowski.

Abstract

In the crystal structure of the title compound, C(21)H(15)BrNO(2) (+)·CF(3)SO(3) (-), the cations form inversion dimers through π-π inter-actions between the acridine ring systems. These dimers are further linked by C-H⋯π and C-Br⋯π inter-actions. The cations and anions are connected by multidirectional C-H⋯O and C-F⋯π inter-actions. The acridine and benzene ring systems are oriented at 10.8 (1)°. The carboxyl group is twisted at an angle of 85.2 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel or almost parallel [inclined at an angle of 1.4 (1)°] in the crystal structure.

Entities: Chemical Disease Gene Species

Year: 2010 PMID： 21579407 PMCID： PMC2979630 DOI： 10.1107/S1600536810016296

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the chemiluminogenic properties of 9-phenoxycarbonyl-10-methylacridinium trifluoromethanesulfonates, see: Adamczyk & Mattingly (2002 ▶); King et al. (2007 ▶); Rak et al. (1999 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2005a ▶,b ▶). For intermolecular interactions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Seo et al. (2009 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Sikorski et al. (2005a ▶,b ▶).

Experimental

Crystal data

C21H15BrNO2 +·CF3O3S− M = 542.32 Monoclinic, a = 9.5755 (2) Å b = 20.4912 (7) Å c = 11.6241 (5) Å β = 104.011 (3)° V = 2212.95 (13) Å3 Z = 4 Mo Kα radiation μ = 2.01 mm−1 T = 295 K 0.37 × 0.15 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.77, T max = 0.92 50472 measured reflections 3910 independent reflections 2200 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.112 S = 0.98 3910 reflections 299 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.62 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016296/om2334sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016296/om2334Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₁₅BrNO₂⁺·CF₃O₃S⁻	F(000) = 1088
M_r = 542.32	D_x = 1.628 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14728 reflections
a = 9.5755 (2) Å	θ = 3.0–29.2°
b = 20.4912 (7) Å	µ = 2.01 mm⁻¹
c = 11.6241 (5) Å	T = 295 K
β = 104.011 (3)°	Plate, yellow
V = 2212.95 (13) Å³	0.37 × 0.15 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3910 independent reflections
Radiation source: enhanced (Mo) X-ray Source	2200 reflections with I > 2σ(I)
graphite	R_int = 0.048
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.1°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −24→24
T_min = 0.77, T_max = 0.92	l = −13→13
50472 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0642P)²] where P = (F_o² + 2F_c²)/3
3910 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	U_iso*/U_eq
C1	0.1494 (3)	0.43387 (19)	0.1754 (3)	0.0703 (10)
H1	0.2493	0.4359	0.1910	0.084*
C2	0.0842 (4)	0.3755 (2)	0.1601 (4)	0.0794 (11)
H2	0.1387	0.3376	0.1642	0.095*
C3	−0.0654 (4)	0.3715 (2)	0.1382 (3)	0.0787 (11)
H3	−0.1092	0.3307	0.1283	0.094*
C4	−0.1483 (3)	0.4255 (2)	0.1309 (3)	0.0684 (10)
H4	−0.2477	0.4213	0.1171	0.082*
C5	−0.1859 (4)	0.6625 (2)	0.1220 (3)	0.0773 (11)
H5	−0.2858	0.6599	0.1022	0.093*
C6	−0.1200 (4)	0.7217 (2)	0.1332 (4)	0.0902 (12)
H6	−0.1766	0.7591	0.1205	0.108*
C7	0.0303 (4)	0.7284 (2)	0.1631 (4)	0.0896 (12)
H7	0.0725	0.7696	0.1708	0.108*
C8	0.1126 (4)	0.67394 (19)	0.1808 (3)	0.0734 (10)
H8	0.2123	0.6781	0.2009	0.088*
C9	0.1328 (3)	0.55402 (17)	0.1829 (3)	0.0544 (8)
N10	−0.1650 (2)	0.54462 (15)	0.1304 (2)	0.0582 (7)
C11	0.0688 (3)	0.49303 (17)	0.1682 (3)	0.0574 (9)
C12	−0.0853 (3)	0.48819 (17)	0.1439 (3)	0.0553 (8)
C13	0.0508 (3)	0.61081 (17)	0.1694 (3)	0.0601 (9)
C14	−0.1030 (3)	0.60523 (18)	0.1404 (3)	0.0596 (9)
C15	0.2939 (3)	0.56004 (16)	0.2072 (3)	0.0573 (8)
O16	0.35203 (19)	0.56616 (11)	0.32302 (19)	0.0620 (6)
O17	0.3586 (2)	0.55888 (15)	0.1321 (2)	0.0855 (8)
C18	0.5032 (3)	0.57634 (17)	0.3564 (3)	0.0521 (8)
C19	0.5556 (3)	0.63811 (17)	0.3571 (3)	0.0606 (9)
H19	0.4934	0.6730	0.3332	0.073*
C20	0.7017 (3)	0.64830 (17)	0.3934 (3)	0.0647 (9)
H20	0.7396	0.6901	0.3933	0.078*
C21	0.7905 (3)	0.59614 (18)	0.4296 (3)	0.0639 (9)
C22	0.7375 (4)	0.5340 (2)	0.4306 (3)	0.0796 (11)
H22	0.7995	0.4992	0.4566	0.095*
C23	0.5906 (4)	0.52369 (18)	0.3924 (3)	0.0713 (10)
H23	0.5522	0.4819	0.3913	0.086*
Br24	0.99257 (4)	0.61111 (2)	0.48030 (5)	0.1038 (2)
C25	−0.3252 (3)	0.5406 (2)	0.1034 (3)	0.0775 (11)
H25A	−0.3609	0.5716	0.1511	0.116*
H25B	−0.3533	0.4974	0.1205	0.116*
H25C	−0.3644	0.5501	0.0210	0.116*
S26	0.47869 (9)	0.82754 (4)	0.30872 (9)	0.0676 (3)
O27	0.6132 (3)	0.79768 (13)	0.3588 (3)	0.0980 (9)
O28	0.4780 (3)	0.89700 (12)	0.3260 (3)	0.1005 (9)
O29	0.3556 (3)	0.79269 (14)	0.3249 (3)	0.1026 (9)
C30	0.4620 (5)	0.8203 (3)	0.1534 (4)	0.1024 (14)
F31	0.5746 (4)	0.8502 (2)	0.1247 (3)	0.1619 (13)
F32	0.4639 (4)	0.75825 (19)	0.1220 (3)	0.1721 (14)
F33	0.3479 (4)	0.8468 (2)	0.0881 (3)	0.1719 (15)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0475 (17)	0.081 (3)	0.084 (3)	0.0049 (19)	0.0198 (16)	0.009 (2)
C2	0.066 (2)	0.077 (3)	0.098 (3)	0.009 (2)	0.025 (2)	0.010 (2)
C3	0.068 (2)	0.074 (3)	0.094 (3)	−0.007 (2)	0.019 (2)	0.005 (2)
C4	0.0476 (17)	0.095 (3)	0.065 (2)	−0.013 (2)	0.0176 (15)	0.004 (2)
C5	0.053 (2)	0.092 (3)	0.086 (3)	0.016 (2)	0.0137 (18)	0.001 (2)
C6	0.077 (3)	0.082 (3)	0.108 (3)	0.027 (2)	0.016 (2)	0.007 (3)
C7	0.073 (2)	0.074 (3)	0.121 (3)	0.004 (2)	0.023 (2)	0.002 (2)
C8	0.0522 (18)	0.075 (3)	0.093 (3)	−0.0007 (19)	0.0168 (17)	0.001 (2)
C9	0.0341 (14)	0.074 (2)	0.056 (2)	0.0012 (15)	0.0129 (13)	−0.0011 (16)
N10	0.0343 (12)	0.083 (2)	0.0595 (17)	0.0019 (14)	0.0148 (11)	−0.0024 (14)
C11	0.0371 (16)	0.078 (3)	0.059 (2)	0.0031 (16)	0.0150 (14)	0.0038 (17)
C12	0.0378 (15)	0.078 (3)	0.051 (2)	−0.0011 (16)	0.0126 (13)	0.0025 (16)
C13	0.0408 (16)	0.077 (3)	0.064 (2)	−0.0013 (17)	0.0166 (14)	0.0001 (17)
C14	0.0418 (16)	0.077 (3)	0.060 (2)	0.0079 (17)	0.0122 (14)	0.0007 (17)
C15	0.0400 (16)	0.068 (2)	0.065 (2)	−0.0002 (14)	0.0159 (17)	0.0015 (17)
O16	0.0393 (10)	0.0869 (17)	0.0597 (15)	−0.0019 (10)	0.0119 (10)	−0.0009 (12)
O17	0.0402 (12)	0.157 (3)	0.0613 (15)	−0.0036 (13)	0.0155 (11)	−0.0026 (15)
C18	0.0389 (15)	0.064 (2)	0.0523 (19)	0.0018 (15)	0.0094 (13)	−0.0004 (16)
C19	0.0491 (18)	0.061 (2)	0.069 (2)	0.0097 (16)	0.0088 (15)	0.0051 (18)
C20	0.0501 (18)	0.060 (2)	0.079 (2)	0.0022 (16)	0.0066 (16)	−0.0022 (18)
C21	0.0429 (16)	0.072 (3)	0.072 (2)	0.0043 (16)	0.0035 (15)	−0.0055 (18)
C22	0.059 (2)	0.067 (3)	0.102 (3)	0.0148 (19)	−0.0019 (19)	0.004 (2)
C23	0.060 (2)	0.058 (2)	0.092 (3)	0.0033 (17)	0.0100 (18)	0.0055 (19)
Br24	0.0442 (2)	0.1080 (4)	0.1442 (5)	0.00493 (19)	−0.0065 (2)	−0.0176 (3)
C25	0.0321 (15)	0.104 (3)	0.093 (3)	0.0019 (17)	0.0103 (15)	−0.012 (2)
S26	0.0539 (5)	0.0615 (6)	0.0876 (7)	0.0009 (4)	0.0176 (4)	0.0017 (5)
O27	0.0639 (14)	0.086 (2)	0.130 (2)	0.0090 (13)	−0.0052 (14)	0.0217 (16)
O28	0.0918 (18)	0.0651 (19)	0.150 (3)	−0.0001 (13)	0.0394 (18)	−0.0211 (16)
O29	0.0775 (16)	0.098 (2)	0.144 (3)	−0.0196 (14)	0.0486 (16)	0.0098 (18)
C30	0.104 (3)	0.100 (4)	0.102 (4)	−0.001 (3)	0.020 (3)	−0.001 (3)
F31	0.162 (3)	0.227 (4)	0.115 (2)	−0.019 (3)	0.069 (2)	0.029 (2)
F32	0.250 (4)	0.141 (3)	0.120 (2)	0.006 (3)	0.034 (2)	−0.052 (2)
F33	0.139 (3)	0.201 (4)	0.134 (3)	0.005 (2)	−0.048 (2)	0.047 (2)

C1—C2	1.342 (5)	C13—C14	1.433 (4)
C1—C11	1.429 (5)	C15—O17	1.187 (4)
C1—H1	0.9300	C15—O16	1.332 (4)
C2—C3	1.395 (5)	O16—C18	1.421 (3)
C2—H2	0.9300	C18—C19	1.361 (4)
C3—C4	1.352 (5)	C18—C23	1.367 (4)
C3—H3	0.9300	C19—C20	1.376 (4)
C4—C12	1.411 (5)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.367 (5)
C5—C6	1.359 (5)	C20—H20	0.9300
C5—C14	1.403 (5)	C21—C22	1.372 (5)
C5—H5	0.9300	C21—Br24	1.906 (3)
C6—C7	1.403 (5)	C22—C23	1.385 (5)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.353 (5)	C23—H23	0.9300
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.415 (5)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C11	1.384 (4)	S26—O27	1.418 (2)
C9—C13	1.391 (4)	S26—O29	1.429 (2)
C9—C15	1.505 (4)	S26—O28	1.438 (3)
N10—C14	1.369 (4)	S26—C30	1.779 (5)
N10—C12	1.374 (4)	C30—F33	1.290 (5)
N10—C25	1.491 (3)	C30—F32	1.325 (5)
C11—C12	1.437 (4)	C30—F31	1.350 (5)

C2—C1—C11	121.5 (3)	C5—C14—C13	118.7 (3)
C2—C1—H1	119.3	O17—C15—O16	125.5 (3)
C11—C1—H1	119.3	O17—C15—C9	123.6 (3)
C1—C2—C3	120.0 (4)	O16—C15—C9	110.8 (3)
C1—C2—H2	120.0	C15—O16—C18	116.0 (2)
C3—C2—H2	120.0	C19—C18—C23	122.3 (3)
C4—C3—C2	121.7 (4)	C19—C18—O16	119.2 (3)
C4—C3—H3	119.1	C23—C18—O16	118.4 (3)
C2—C3—H3	119.1	C18—C19—C20	119.3 (3)
C3—C4—C12	120.6 (3)	C18—C19—H19	120.4
C3—C4—H4	119.7	C20—C19—H19	120.4
C12—C4—H4	119.7	C21—C20—C19	119.1 (3)
C6—C5—C14	120.0 (3)	C21—C20—H20	120.5
C6—C5—H5	120.0	C19—C20—H20	120.5
C14—C5—H5	120.0	C20—C21—C22	121.7 (3)
C5—C6—C7	122.4 (4)	C20—C21—Br24	118.6 (3)
C5—C6—H6	118.8	C22—C21—Br24	119.8 (2)
C7—C6—H6	118.8	C21—C22—C23	119.2 (3)
C8—C7—C6	118.8 (4)	C21—C22—H22	120.4
C8—C7—H7	120.6	C23—C22—H22	120.4
C6—C7—H7	120.6	C18—C23—C22	118.4 (3)
C7—C8—C13	121.6 (3)	C18—C23—H23	120.8
C7—C8—H8	119.2	C22—C23—H23	120.8
C13—C8—H8	119.2	N10—C25—H25A	109.5
C11—C9—C13	121.4 (3)	N10—C25—H25B	109.5
C11—C9—C15	120.0 (3)	H25A—C25—H25B	109.5
C13—C9—C15	118.5 (3)	N10—C25—H25C	109.5
C14—N10—C12	122.4 (2)	H25A—C25—H25C	109.5
C14—N10—C25	118.1 (3)	H25B—C25—H25C	109.5
C12—N10—C25	119.5 (3)	O27—S26—O29	115.25 (18)
C9—C11—C1	122.9 (3)	O27—S26—O28	113.86 (17)
C9—C11—C12	119.3 (3)	O29—S26—O28	116.39 (17)
C1—C11—C12	117.9 (3)	O27—S26—C30	103.3 (2)
N10—C12—C4	122.8 (3)	O29—S26—C30	102.6 (2)
N10—C12—C11	118.7 (3)	O28—S26—C30	102.8 (2)
C4—C12—C11	118.4 (3)	F33—C30—F32	107.9 (4)
C9—C13—C8	122.8 (3)	F33—C30—F31	106.0 (4)
C9—C13—C14	118.6 (3)	F32—C30—F31	107.6 (5)
C8—C13—C14	118.5 (3)	F33—C30—S26	114.7 (4)
N10—C14—C5	121.8 (3)	F32—C30—S26	110.9 (4)
N10—C14—C13	119.5 (3)	F31—C30—S26	109.4 (3)

C11—C1—C2—C3	−0.8 (6)	C6—C5—C14—C13	−0.8 (5)
C1—C2—C3—C4	0.4 (6)	C9—C13—C14—N10	2.0 (5)
C2—C3—C4—C12	0.8 (6)	C8—C13—C14—N10	−179.2 (3)
C14—C5—C6—C7	−0.2 (6)	C9—C13—C14—C5	−177.4 (3)
C5—C6—C7—C8	0.5 (7)	C8—C13—C14—C5	1.4 (5)
C6—C7—C8—C13	0.2 (6)	C11—C9—C15—O17	82.6 (4)
C13—C9—C11—C1	176.7 (3)	C13—C9—C15—O17	−93.9 (4)
C15—C9—C11—C1	0.3 (5)	C11—C9—C15—O16	−96.8 (3)
C13—C9—C11—C12	−2.9 (5)	C13—C9—C15—O16	86.6 (4)
C15—C9—C11—C12	−179.4 (3)	O17—C15—O16—C18	4.3 (5)
C2—C1—C11—C9	−179.7 (3)	C9—C15—O16—C18	−176.2 (3)
C2—C1—C11—C12	−0.1 (5)	C15—O16—C18—C19	85.8 (4)
C14—N10—C12—C4	−178.4 (3)	C15—O16—C18—C23	−97.4 (3)
C25—N10—C12—C4	1.3 (4)	C23—C18—C19—C20	1.0 (5)
C14—N10—C12—C11	−0.6 (4)	O16—C18—C19—C20	177.7 (3)
C25—N10—C12—C11	179.1 (3)	C18—C19—C20—C21	−1.0 (5)
C3—C4—C12—N10	176.1 (3)	C19—C20—C21—C22	0.0 (5)
C3—C4—C12—C11	−1.7 (5)	C19—C20—C21—Br24	−179.7 (3)
C9—C11—C12—N10	3.0 (4)	C20—C21—C22—C23	0.9 (6)
C1—C11—C12—N10	−176.6 (3)	Br24—C21—C22—C23	−179.4 (3)
C9—C11—C12—C4	−179.1 (3)	C19—C18—C23—C22	−0.1 (5)
C1—C11—C12—C4	1.3 (4)	O16—C18—C23—C22	−176.8 (3)
C11—C9—C13—C8	−178.3 (3)	C21—C22—C23—C18	−0.9 (6)
C15—C9—C13—C8	−1.8 (5)	O27—S26—C30—F33	−177.5 (4)
C11—C9—C13—C14	0.5 (5)	O29—S26—C30—F33	62.4 (4)
C15—C9—C13—C14	176.9 (3)	O28—S26—C30—F33	−58.8 (4)
C7—C8—C13—C9	177.7 (4)	O27—S26—C30—F32	60.0 (4)
C7—C8—C13—C14	−1.1 (5)	O29—S26—C30—F32	−60.2 (4)
C12—N10—C14—C5	177.5 (3)	O28—S26—C30—F32	178.7 (4)
C25—N10—C14—C5	−2.2 (5)	O27—S26—C30—F31	−58.5 (4)
C12—N10—C14—C13	−1.9 (5)	O29—S26—C30—F31	−178.6 (3)
C25—N10—C14—C13	178.4 (3)	O28—S26—C30—F31	60.2 (4)
C6—C5—C14—N10	179.8 (3)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O27ⁱ	0.93	2.59	3.361 (5)	141
C4—H4···O28ⁱⁱ	0.93	2.50	3.365 (4)	155
C20—H20···O27	0.93	2.50	3.176 (4)	130
C25—H25A···Cg4ⁱⁱⁱ	0.96	2.81	3.569 (4)	136
C25—H25B···O28ⁱⁱ	0.96	2.53	3.472 (5)	167

X	I	J	I···J	X···J	X–I···J
C21	Br24	Cg1^iv	3.958 (2)	4.158 (3)	82.3 (1)
C21	Br24	Cg3^iv	3.937 (2)	4.235 (4)	85.4 (2)
C30	F31	Cg4^v	3.212 (4)	4.305 (5)	137.5 (3)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2^vi	3.650 (2)	2.82 (16)	3.623 (2)	0.444 (2)
2	1^vi	3.650 (2)	2.82 (16)	3.623 (2)	0.444 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O27ⁱ	0.93	2.59	3.361 (5)	141
C4—H4⋯O28ⁱⁱ	0.93	2.50	3.365 (4)	155
C20—H20⋯O27	0.93	2.50	3.176 (4)	130
C25—H25A⋯Cg4ⁱⁱⁱ	0.96	2.81	3.569 (4)	136
C25—H25B⋯O28ⁱⁱ	0.96	2.53	3.472 (5)	167

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

C–Br⋯π and C–F⋯π interactions (Å,°)

Cg1, Cg3 and Cg4 are the centroids of the C9/N10/C11–C14, C5–C8/C13/C14 and C18–C23 rings, respectively.

X	I	J	I⋯J	X⋯J	X–I⋯J
C21	Br24	Cg1^iv	3.958 (2)	4.158 (3)	82.3 (1)
C21	Br24	Cg3^iv	3.937 (2)	4.235 (4)	85.4 (2)
C30	F31	Cg4^v	3.212 (4)	4.305 (5)	137.5 (3)

Symmetry codes: (iv) ; (v) .

Table 3

π–π interactions (Å,°)

Cg1 and Cg2 are the centroids of the C9/N10/C11–C14 and C1–C4/C11/C12 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2^vi	3.650 (2)	2.82 (16)	3.623 (2)	0.444 (2)

Symmetry code: (vi) .

6 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Toward an Understanding of the Chemiluminescence Accompanying the Reaction of 9-Carboxy-10-methylacridinium Phenyl Ester with Hydrogen Peroxide.

Authors: Janusz Rak; Piotr Skurski; Jerzy Blazejowski
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

3. 5-Bromo-2,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

Authors: Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-08-29

4. Flow injection analysis of H2O2 in natural waters using acridinium ester chemiluminescence: method development and optimization using a kinetic model.

Authors: D Whitney King; William J Cooper; Steven A Rusak; Barrie M Peake; James J Kiddle; Daniel W O'Sullivan; Megan L Melamed; Chris R Morgan; Stephen M Theberge
Journal: Anal Chem Date: 2007-04-25 Impact factor: 6.986

5. Experimental electron density study of the supramolecular aggregation between 4,4'-dipyridyl-N,N'-dioxide and 1,4-diiodotetrafluorobenzene at 90 K.

Authors: Riccardo Bianchi; Alessandra Forni; Tullio Pilati
Journal: Acta Crystallogr B Date: 2004-09-15

6. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20