Literature DB >> 21201404

10-Methyl-9-(2-nitro-phenoxy-carbon-yl)acridinium trifluoro-methane-sulfonate.

Artur Sikorski, Agnieszka Niziołek, Karol Krzymiński, Tadeusz Lis, Jerzy Błażejowski.

Abstract

The crystal structure of the title compound, C(21)H(15)N(2)O(4) (+)·CF(3)O(3)S(-), is stabilized by C-H⋯O and C-H⋯F hydrogen bonds, by C-F⋯π, N-O⋯π and S-O⋯π inter-actions, and by O⋯O [2.70 (4) Å] and O⋯F [2.85 (1) or 2.92 (1) Å] contacts; π-π interactions are also present. In the packing of the mol-ecules, acridine units are either parallel or inclined at an angle of 12.5 (1)°. The nitrophenoxycarbonyl unit is disordered over two position; the site occupancy factors are 0.89 and 0.11.

Entities: CellLine Chemical Disease Species

Year: 2008 PMID： 21201404 PMCID： PMC2960374 DOI： 10.1107/S1600536807068109

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

Related literature

For general background, see: Adamczyk et al. (2004 ▶); Becker et al. (1999 ▶); Rak et al. (1999 ▶); Razavi & McCapra (2000a ▶,b ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Bianchi et al. (2004 ▶); Butcher et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter & Sanders (1990 ▶); Kaafarani et al. (2003 ▶); Lyssenko & Antipin (2004 ▶); Sato (1996 ▶); Sikorski et al. (2007 ▶); Sridhar et al. (2006 ▶); Steiner (1999 ▶). For analysis of intermolecular interactions, see: Spek (2003 ▶).

Experimental

Crystal data

C21H15N2O4 +·CF3O3S− M = 508.42 Monoclinic, a = 12.459 (4) Å b = 21.361 (6) Å c = 8.123 (3) Å β = 108.42 (3)° V = 2051.1 (12) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 100 (2) K 0.40 × 0.10 × 0.02 mm

Data collection

Kuma KM-4 CCD κ-geometry diffractometer Absorption correction: none 22835 measured reflections 3671 independent reflections 2959 reflections with I > 2σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.064 wR(F 2) = 0.130 S = 1.20 3671 reflections 366 parameters 21 restraints H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.36 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068109/xu2382sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068109/xu2382Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₁₅N₂O₄⁺·CF₃O₃S^–	F₀₀₀ = 1040
M_r = 508.42	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 500-502 K K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 12.459 (4) Å	Cell parameters from 22931 reflections
b = 21.361 (6) Å	θ = 4.6–32.0º
c = 8.123 (3) Å	µ = 0.24 mm⁻¹
β = 108.42 (3)º	T = 100 (2) K
V = 2051.1 (12) Å³	Plate, yellow
Z = 4	0.40 × 0.10 × 0.02 mm

Kuma KM4 CCD κ-geometry diffractometer	2959 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.079
Monochromator: graphite	θ_max = 25.3º
T = 100(2) K	θ_min = 4.6º
ω scans	h = −14→14
Absorption correction: none	k = −25→25
22835 measured reflections	l = −9→9
3671 independent reflections

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max < 0.001
3671 reflections	Δρ_max = 0.27 e Å⁻³
366 parameters	Δρ_min = −0.36 e Å⁻³
21 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5397 (2)	0.49641 (14)	0.8189 (4)	0.0232 (7)
H1	0.6035	0.5134	0.9052	0.028*
C2	0.5215 (2)	0.43405 (14)	0.8152 (4)	0.0244 (7)
H2	0.5736	0.4074	0.8954	0.029*
C3	0.4250 (2)	0.40863 (14)	0.6920 (4)	0.0256 (7)
H3	0.4112	0.3649	0.6926	0.031*
C4	0.3514 (3)	0.44534 (14)	0.5727 (4)	0.0270 (7)
H4	0.2861	0.4272	0.4923	0.032*
C5	0.2406 (3)	0.64981 (14)	0.3137 (4)	0.0259 (7)
H5	0.1804	0.6312	0.2244	0.031*
C6	0.2548 (3)	0.71290 (15)	0.3180 (4)	0.0270 (7)
H6	0.2043	0.7379	0.2307	0.032*
C7	0.3419 (3)	0.74185 (14)	0.4480 (4)	0.0276 (7)
H7	0.3494	0.7861	0.4485	0.033*
C8	0.4158 (3)	0.70724 (14)	0.5734 (4)	0.0259 (7)
H8	0.4750	0.7274	0.6608	0.031*
C9	0.4804 (2)	0.60253 (14)	0.6994 (4)	0.0228 (7)
N10	0.30150 (19)	0.54800 (11)	0.4416 (3)	0.0202 (6)
C11	0.4655 (2)	0.53731 (14)	0.6964 (3)	0.0198 (7)
C12	0.3708 (2)	0.51042 (13)	0.5666 (3)	0.0197 (7)
C13	0.4053 (2)	0.64062 (14)	0.5748 (3)	0.0217 (7)
C14	0.3153 (2)	0.61197 (14)	0.4420 (4)	0.0214 (7)
C15	0.5682 (3)	0.63250 (16)	0.8509 (5)	0.0203 (8)	0.886 (4)
O16	0.6746 (2)	0.61632 (10)	0.8552 (3)	0.0228 (6)	0.886 (4)
O17	0.54773 (18)	0.66490 (10)	0.9577 (3)	0.0233 (6)	0.886 (4)
C18	0.7648 (3)	0.63594 (16)	1.0013 (5)	0.0214 (8)	0.886 (4)
C19	0.8199 (4)	0.5892 (2)	1.1130 (6)	0.0238 (11)	0.886 (4)
H19	0.7951	0.5471	1.0913	0.029*	0.886 (4)
C20	0.9110 (6)	0.6034 (4)	1.2562 (16)	0.024 (3)	0.886 (4)
H20	0.9488	0.5717	1.3352	0.028*	0.886 (4)
C21	0.9461 (6)	0.6656 (4)	1.2820 (10)	0.0287 (19)	0.886 (4)
H21	1.0091	0.6757	1.3801	0.034*	0.886 (4)
C22	0.8935 (5)	0.7129 (3)	1.1712 (8)	0.0236 (16)	0.886 (4)
H22	0.9202	0.7548	1.1900	0.028*	0.886 (4)
C23	0.8005 (4)	0.69750 (19)	1.0318 (7)	0.0237 (13)	0.886 (4)
N24	0.7429 (3)	0.74990 (16)	0.9243 (5)	0.0288 (8)	0.886 (4)
O25	0.7664 (7)	0.8028 (5)	0.9836 (11)	0.054 (3)	0.886 (4)
O26	0.6766 (2)	0.73880 (12)	0.7809 (3)	0.0415 (8)	0.886 (4)
C15A	0.612 (2)	0.6275 (10)	0.776 (3)	0.016 (5)*	0.114 (4)
O16A	0.6247 (17)	0.6231 (8)	0.943 (3)	0.022 (5)*	0.114 (4)
O17A	0.6748 (15)	0.6451 (8)	0.706 (2)	0.026 (5)*	0.114 (4)
C18A	0.737 (2)	0.6387 (8)	1.058 (4)	0.015 (7)*	0.114 (4)
C19A	0.801 (2)	0.5901 (16)	1.155 (4)	0.022 (12)*	0.114 (4)
H19A	0.7753	0.5480	1.1409	0.027*	0.114 (4)
C20A	0.905 (4)	0.607 (3)	1.273 (13)	0.04 (4)*	0.114 (4)
H20A	0.9403	0.5732	1.3464	0.053*	0.114 (4)
C21A	0.968 (3)	0.662 (2)	1.307 (6)	0.000 (10)*	0.114 (4)
H21A	1.0423	0.6690	1.3819	0.000*	0.114 (4)
C22A	0.890 (3)	0.703 (2)	1.202 (5)	0.000 (10)*	0.114 (4)
H22A	0.9125	0.7456	1.2248	0.000*	0.114 (4)
C23A	0.786 (3)	0.6977 (13)	1.071 (5)	0.018 (13)*	0.114 (4)
N24A	0.718 (2)	0.7556 (14)	0.982 (4)	0.020 (8)*	0.114 (4)
O25A	0.762 (3)	0.802 (2)	0.974 (5)	0.000 (8)*	0.114 (4)
O26A	0.6136 (15)	0.7479 (8)	0.911 (2)	0.027 (5)*	0.114 (4)
C27	0.2090 (3)	0.51967 (15)	0.3011 (4)	0.0317 (8)
H27A	0.1377	0.5242	0.3271	0.047*
H27B	0.2249	0.4751	0.2912	0.047*
H27C	0.2027	0.5408	0.1914	0.047*
S28	0.15313 (6)	0.90846 (3)	0.25166 (9)	0.0233 (2)
O29	0.11820 (19)	0.95900 (10)	0.1300 (3)	0.0358 (6)
O30	0.23911 (17)	0.92471 (11)	0.4117 (3)	0.0357 (6)
O31	0.16858 (18)	0.84963 (10)	0.1774 (3)	0.0330 (6)
C32	0.0297 (3)	0.89497 (15)	0.3214 (4)	0.0277 (7)
F33	0.00993 (15)	0.94384 (9)	0.4102 (2)	0.0424 (5)
F34	0.04372 (16)	0.84469 (9)	0.4239 (2)	0.0420 (5)
F35	−0.06374 (14)	0.88552 (9)	0.1871 (2)	0.0383 (5)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0183 (16)	0.0225 (17)	0.0237 (16)	−0.0010 (12)	−0.0004 (13)	−0.0002 (14)
C2	0.0232 (17)	0.0199 (17)	0.0269 (17)	0.0035 (13)	0.0037 (14)	0.0013 (14)
C3	0.0242 (18)	0.0209 (17)	0.0296 (17)	−0.0006 (13)	0.0055 (15)	−0.0024 (14)
C4	0.0269 (18)	0.0261 (18)	0.0244 (17)	−0.0034 (14)	0.0028 (14)	−0.0041 (14)
C5	0.0242 (18)	0.0297 (19)	0.0185 (16)	0.0031 (14)	−0.0006 (13)	0.0014 (14)
C6	0.0268 (18)	0.0278 (18)	0.0245 (17)	0.0045 (14)	0.0054 (14)	0.0054 (15)
C7	0.0272 (18)	0.0215 (17)	0.0321 (18)	0.0013 (14)	0.0067 (15)	0.0041 (15)
C8	0.0236 (17)	0.0201 (17)	0.0292 (17)	−0.0014 (13)	0.0014 (14)	0.0014 (14)
C9	0.0226 (17)	0.0209 (17)	0.0229 (16)	−0.0027 (13)	0.0043 (13)	0.0015 (14)
N10	0.0196 (13)	0.0203 (13)	0.0180 (13)	0.0000 (10)	0.0018 (11)	−0.0008 (11)
C11	0.0180 (16)	0.0235 (17)	0.0188 (15)	−0.0017 (12)	0.0071 (13)	−0.0028 (13)
C12	0.0185 (16)	0.0221 (16)	0.0189 (15)	−0.0017 (12)	0.0065 (13)	−0.0024 (13)
C13	0.0191 (16)	0.0253 (17)	0.0204 (15)	0.0002 (13)	0.0057 (13)	0.0024 (14)
C14	0.0215 (17)	0.0241 (17)	0.0201 (16)	−0.0010 (13)	0.0087 (13)	0.0002 (14)
C15	0.022 (2)	0.0167 (19)	0.022 (2)	0.0029 (15)	0.0066 (19)	0.0084 (17)
O16	0.0190 (14)	0.0237 (13)	0.0220 (14)	0.0007 (10)	0.0013 (12)	−0.0028 (11)
O17	0.0247 (14)	0.0191 (13)	0.0240 (13)	0.0000 (10)	0.0048 (11)	−0.0015 (11)
C18	0.017 (2)	0.027 (2)	0.021 (2)	−0.0016 (15)	0.0064 (18)	−0.0052 (17)
C19	0.024 (2)	0.022 (2)	0.024 (2)	0.0007 (16)	0.006 (2)	−0.0038 (18)
C20	0.023 (4)	0.024 (4)	0.024 (3)	0.0065 (17)	0.007 (3)	0.002 (2)
C21	0.018 (3)	0.040 (4)	0.021 (3)	0.003 (3)	−0.005 (3)	−0.002 (2)
C22	0.025 (3)	0.021 (3)	0.026 (3)	−0.0035 (18)	0.009 (2)	0.002 (2)
C23	0.023 (2)	0.021 (3)	0.026 (3)	0.0007 (15)	0.006 (2)	0.0054 (18)
N24	0.0216 (19)	0.031 (2)	0.029 (2)	−0.0035 (15)	0.0013 (18)	0.0065 (17)
O25	0.052 (3)	0.022 (2)	0.074 (4)	−0.0030 (15)	0.001 (2)	0.0051 (18)
O26	0.0337 (16)	0.0399 (16)	0.0378 (17)	−0.0129 (12)	−0.0075 (14)	0.0188 (13)
C27	0.0317 (19)	0.0291 (18)	0.0226 (16)	0.0004 (15)	−0.0078 (14)	0.0004 (15)
S28	0.0229 (4)	0.0225 (4)	0.0223 (4)	−0.0002 (3)	0.0039 (3)	−0.0007 (3)
O29	0.0486 (15)	0.0244 (12)	0.0308 (12)	−0.0008 (10)	0.0075 (11)	0.0056 (10)
O30	0.0236 (12)	0.0456 (14)	0.0315 (12)	−0.0035 (10)	−0.0004 (10)	−0.0030 (11)
O31	0.0359 (14)	0.0275 (12)	0.0359 (13)	0.0074 (10)	0.0118 (11)	−0.0043 (11)
C32	0.0272 (19)	0.0307 (19)	0.0198 (16)	0.0020 (14)	−0.0003 (14)	−0.0047 (15)
F33	0.0330 (11)	0.0523 (13)	0.0413 (11)	0.0043 (9)	0.0112 (9)	−0.0191 (10)
F34	0.0447 (12)	0.0468 (13)	0.0325 (11)	−0.0133 (9)	0.0095 (9)	0.0070 (10)
F35	0.0232 (10)	0.0496 (12)	0.0348 (11)	−0.0054 (8)	−0.0012 (9)	−0.0076 (9)

C1—C2	1.350 (4)	C20—H20	0.9500
C1—C11	1.423 (4)	C21—C22	1.374 (7)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.408 (4)	C22—C23	1.380 (5)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.354 (4)	C23—N24	1.461 (6)
C3—H3	0.9500	N24—O26	1.219 (4)
C4—C12	1.415 (4)	N24—O25	1.227 (10)
C4—H4	0.9500	C15A—O17A	1.17 (3)
C5—C6	1.358 (4)	C15A—O16A	1.31 (3)
C5—C14	1.411 (4)	O16A—C18A	1.46 (3)
C5—H5	0.9500	C18A—C19A	1.390 (8)
C6—C7	1.396 (4)	C18A—C23A	1.390 (8)
C6—H6	0.9500	C19A—C20A	1.390 (8)
C7—C8	1.356 (4)	C19A—H19A	0.9500
C7—H7	0.9500	C20A—C21A	1.390 (8)
C8—C13	1.430 (4)	C20A—H20A	0.9500
C8—H8	0.9500	C21A—C22A	1.390 (8)
C9—C13	1.401 (4)	C21A—H21A	0.9500
C9—C11	1.405 (4)	C22A—C23A	1.390 (8)
C9—C15	1.506 (5)	C22A—H22A	0.9500
C9—C15A	1.65 (3)	C23A—N24A	1.54 (5)
N10—C12	1.366 (4)	N24A—O25A	1.13 (6)
N10—C14	1.377 (4)	N24A—O26A	1.26 (3)
N10—C27	1.472 (4)	C27—H27A	0.9800
C11—C12	1.431 (4)	C27—H27B	0.9800
C13—C14	1.426 (4)	C27—H27C	0.9800
C15—O17	1.199 (4)	S28—O31	1.433 (2)
C15—O16	1.361 (5)	S28—O29	1.435 (2)
O16—C18	1.415 (4)	S28—O30	1.441 (2)
C18—C19	1.378 (5)	S28—C32	1.821 (3)
C18—C23	1.385 (5)	C32—F35	1.335 (3)
C19—C20	1.378 (6)	C32—F33	1.336 (3)
C19—H19	0.9500	C32—F34	1.336 (4)
C20—C21	1.393 (6)

C2—C1—C11	121.5 (3)	C21—C20—H20	120.9
C2—C1—H1	119.2	C22—C21—C20	122.7 (7)
C11—C1—H1	119.2	C22—C21—H21	118.7
C1—C2—C3	119.8 (3)	C20—C21—H21	118.7
C1—C2—H2	120.1	C21—C22—C23	117.8 (6)
C3—C2—H2	120.1	C21—C22—H22	121.1
C4—C3—C2	121.2 (3)	C23—C22—H22	121.1
C4—C3—H3	119.4	C22—C23—C18	120.8 (5)
C2—C3—H3	119.4	C22—C23—N24	115.8 (4)
C3—C4—C12	120.6 (3)	C18—C23—N24	123.4 (4)
C3—C4—H4	119.7	O26—N24—O25	124.0 (5)
C12—C4—H4	119.7	O26—N24—C23	118.6 (3)
C6—C5—C14	119.9 (3)	O25—N24—C23	117.3 (5)
C6—C5—H5	120.0	O17A—C15A—O16A	130 (3)
C14—C5—H5	120.0	O17A—C15A—C9	131 (2)
C5—C6—C7	121.5 (3)	O16A—C15A—C9	98.7 (19)
C5—C6—H6	119.2	C15A—O16A—C18A	115 (2)
C7—C6—H6	119.2	C19A—C18A—C23A	118 (3)
C8—C7—C6	120.5 (3)	C19A—C18A—O16A	117 (2)
C8—C7—H7	119.7	C23A—C18A—O16A	125 (2)
C6—C7—H7	119.7	C18A—C19A—C20A	116 (4)
C7—C8—C13	120.4 (3)	C18A—C19A—H19A	122.0
C7—C8—H8	119.8	C20A—C19A—H19A	122.0
C13—C8—H8	119.8	C19A—C20A—C21A	134 (6)
C13—C9—C11	120.6 (3)	C19A—C20A—H20A	112.9
C13—C9—C15	119.3 (3)	C21A—C20A—H20A	112.9
C11—C9—C15	119.6 (3)	C22A—C21A—C20A	100 (5)
C13—C9—C15A	116.3 (9)	C22A—C21A—H21A	130.0
C11—C9—C15A	116.0 (9)	C20A—C21A—H21A	130.0
C12—N10—C14	122.2 (2)	C23A—C22A—C21A	136 (4)
C12—N10—C27	119.4 (2)	C23A—C22A—H22A	112.2
C14—N10—C27	118.4 (2)	C21A—C22A—H22A	112.2
C9—C11—C1	122.9 (3)	C22A—C23A—C18A	114 (3)
C9—C11—C12	119.0 (3)	C22A—C23A—N24A	122 (3)
C1—C11—C12	118.1 (3)	C18A—C23A—N24A	122 (3)
N10—C12—C4	121.9 (3)	O25A—N24A—O26A	122 (3)
N10—C12—C11	119.5 (3)	O25A—N24A—C23A	121 (3)
C4—C12—C11	118.6 (3)	O26A—N24A—C23A	117 (2)
C9—C13—C14	118.9 (3)	N10—C27—H27A	109.5
C9—C13—C8	122.8 (3)	N10—C27—H27B	109.5
C14—C13—C8	118.2 (3)	H27A—C27—H27B	109.5
N10—C14—C5	120.9 (3)	N10—C27—H27C	109.5
N10—C14—C13	119.7 (3)	H27A—C27—H27C	109.5
C5—C14—C13	119.4 (3)	H27B—C27—H27C	109.5
O17—C15—O16	123.8 (3)	O31—S28—O29	114.95 (13)
O17—C15—C9	124.8 (3)	O31—S28—O30	115.49 (13)
O16—C15—C9	111.3 (3)	O29—S28—O30	114.64 (14)
C15—O16—C18	117.1 (3)	O31—S28—C32	103.36 (14)
C19—C18—C23	120.4 (4)	O29—S28—C32	103.35 (14)
C19—C18—O16	115.8 (3)	O30—S28—C32	102.57 (13)
C23—C18—O16	123.8 (3)	F35—C32—F33	107.3 (2)
C20—C19—C18	120.1 (5)	F35—C32—F34	107.2 (3)
C20—C19—H19	119.9	F33—C32—F34	107.5 (2)
C18—C19—H19	119.9	F35—C32—S28	112.0 (2)
C19—C20—C21	118.2 (6)	F33—C32—S28	111.3 (2)
C19—C20—H20	120.9	F34—C32—S28	111.4 (2)

C11—C1—C2—C3	−2.3 (4)	C15—O16—C18—C23	−71.5 (5)
C1—C2—C3—C4	2.2 (4)	C23—C18—C19—C20	0.1 (10)
C2—C3—C4—C12	1.2 (4)	O16—C18—C19—C20	178.1 (8)
C14—C5—C6—C7	−0.4 (4)	C18—C19—C20—C21	−1.1 (15)
C5—C6—C7—C8	0.6 (4)	C19—C20—C21—C22	0.3 (17)
C6—C7—C8—C13	−0.3 (4)	C20—C21—C22—C23	1.6 (13)
C13—C9—C11—C1	179.5 (3)	C21—C22—C23—C18	−2.6 (10)
C15—C9—C11—C1	−8.7 (4)	C21—C22—C23—N24	176.1 (6)
C15A—C9—C11—C1	30.1 (10)	C19—C18—C23—C22	1.9 (9)
C13—C9—C11—C12	−1.5 (4)	O16—C18—C23—C22	−175.9 (5)
C15—C9—C11—C12	170.4 (3)	C19—C18—C23—N24	−176.8 (5)
C15A—C9—C11—C12	−150.9 (10)	O16—C18—C23—N24	5.4 (8)
C2—C1—C11—C9	178.3 (3)	C22—C23—N24—O26	164.5 (5)
C2—C1—C11—C12	−0.7 (4)	C18—C23—N24—O26	−16.8 (8)
C14—N10—C12—C4	175.3 (3)	C22—C23—N24—O25	−14.1 (9)
C27—N10—C12—C4	−4.8 (4)	C18—C23—N24—O25	164.6 (6)
C14—N10—C12—C11	−4.1 (4)	C13—C9—C15A—O17A	−50 (3)
C27—N10—C12—C11	175.7 (2)	C11—C9—C15A—O17A	101 (3)
C3—C4—C12—N10	176.2 (3)	C15—C9—C15A—O17A	−154 (4)
C3—C4—C12—C11	−4.3 (4)	C13—C9—C15A—O16A	128.8 (13)
C9—C11—C12—N10	4.4 (4)	C11—C9—C15A—O16A	−80.5 (16)
C1—C11—C12—N10	−176.5 (2)	C15—C9—C15A—O16A	24.6 (10)
C9—C11—C12—C4	−175.1 (3)	O17A—C15A—O16A—C18A	−4(4)
C1—C11—C12—C4	4.0 (4)	C9—C15A—O16A—C18A	176.8 (14)
C11—C9—C13—C14	−1.7 (4)	C15A—O16A—C18A—C19A	−112 (3)
C15—C9—C13—C14	−173.6 (3)	C15A—O16A—C18A—C23A	65 (4)
C15A—C9—C13—C14	147.6 (10)	C23A—C18A—C19A—C20A	7(7)
C11—C9—C13—C8	179.1 (3)	O16A—C18A—C19A—C20A	−175 (6)
C15—C9—C13—C8	7.3 (4)	C18A—C19A—C20A—C21A	−8(14)
C15A—C9—C13—C8	−31.5 (10)	C19A—C20A—C21A—C22A	8(13)
C7—C8—C13—C9	178.9 (3)	C20A—C21A—C22A—C23A	−11 (9)
C7—C8—C13—C14	−0.3 (4)	C21A—C22A—C23A—C18A	13 (8)
C12—N10—C14—C5	−178.3 (2)	C21A—C22A—C23A—N24A	178 (5)
C27—N10—C14—C5	1.8 (4)	C19A—C18A—C23A—C22A	−9(5)
C12—N10—C14—C13	0.9 (4)	O16A—C18A—C23A—C22A	174 (3)
C27—N10—C14—C13	−178.9 (2)	C19A—C18A—C23A—N24A	−174 (3)
C6—C5—C14—N10	179.1 (3)	O16A—C18A—C23A—N24A	9(5)
C6—C5—C14—C13	−0.2 (4)	C22A—C23A—N24A—O25A	27 (6)
C9—C13—C14—N10	2.0 (4)	C18A—C23A—N24A—O25A	−169 (4)
C8—C13—C14—N10	−178.7 (2)	C22A—C23A—N24A—O26A	−157 (4)
C9—C13—C14—C5	−178.7 (3)	C18A—C23A—N24A—O26A	7(5)
C8—C13—C14—C5	0.5 (4)	O31—S28—C32—F35	−66.2 (2)
C13—C9—C15—O17	61.8 (4)	O29—S28—C32—F35	53.9 (2)
C11—C9—C15—O17	−110.2 (4)	O30—S28—C32—F35	173.4 (2)
C15A—C9—C15—O17	156.3 (16)	O31—S28—C32—F33	173.78 (19)
C13—C9—C15—O16	−120.4 (3)	O29—S28—C32—F33	−66.1 (2)
C11—C9—C15—O16	67.6 (4)	O30—S28—C32—F33	53.4 (2)
C15A—C9—C15—O16	−25.9 (15)	O31—S28—C32—F34	53.8 (2)
O17—C15—O16—C18	4.3 (5)	O29—S28—C32—F34	173.94 (19)
C9—C15—O16—C18	−173.5 (3)	O30—S28—C32—F34	−66.6 (2)
C15—O16—C18—C19	110.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O30ⁱ	0.95	2.39	3.111 (4)	132
C3—H3···O25ⁱ	0.95	2.59	3.268 (10)	129
C5—H5···F34ⁱⁱ	0.95	2.55	3.339 (4)	141
C6—H6···O31	0.95	2.44	3.196 (4)	136
C20—H20···O29ⁱ	0.95	2.59	3.273 (9)	129
C27—H27A···O29ⁱⁱⁱ	0.98	2.57	3.246 (4)	126
C27—H27C···O30ⁱⁱ	0.98	2.56	3.508 (4)	162

X	I	J	I···J	X···J	X-I···J
C32	F33	Cg4^iv	3.690 (4)	4.002 (5)	93.6 (2)
C32	F33	Cg4A^iv	3.949 (18)	4.31 (2)	96.6 (3)
C32	F34	Cg4^iv	3.356 (4)	4.002 (5)	109.3 (2)
C32	F34	Cg4A^iv	3.663 (18)	4.31 (2)	110.3 (3)
N24	O25	Cg4ⁱⁱ	3.443 (9)	3.710 (5)	92.7 (5)
N24	O25	Cg4Aⁱⁱ	3.13 (2)	3.45 (2)	94.8 (6)
N24A	O25A	Cg4ⁱⁱ	3.41 (4)	4.19 (3)	126 (3)
N24A	O25A	Cg4Aⁱⁱ	3.10 (4)	3.91 (3)	128 (3)
S28	O30	Cg1ⁱⁱ	3.810 (3)	3.707 (2)	74.9 (1)
S28	O31	Cg1ⁱⁱ	3.529 (3)	3.707 (2)	85.6 (1)
S28	O31	Cg3ⁱⁱ	3.205 (3)	4.221 (2)	126.7 (1)

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
1	2^v	3.547 (2)	3.4	3.504 (3)	0.556 (3)
2	2^v	3.981 (2)	0.0	3.504 (3)	1.891 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O30ⁱ	0.95	2.39	3.111 (4)	132
C3—H3⋯O25ⁱ	0.95	2.59	3.268 (10)	129
C5—H5⋯F34ⁱⁱ	0.95	2.55	3.339 (4)	141
C6—H6⋯O31	0.95	2.44	3.196 (4)	136
C20—H20⋯O29ⁱ	0.95	2.59	3.273 (9)	129
C27—H27A⋯O29ⁱⁱⁱ	0.98	2.57	3.246 (4)	126
C27—H27C⋯O30ⁱⁱ	0.98	2.56	3.508 (4)	162

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

Table 2

C—F⋯π, N—O⋯π and S—O⋯π interactions (Å,°)

X	I	J	I⋯J	X⋯J	X—I⋯J
C32	F33	Cg4^iv	3.690 (4)	4.002 (5)	93.6 (2)
C32	F33	Cg4A^iv	3.949 (18)	4.31 (2)	96.6 (3)
C32	F34	Cg4^iv	3.356 (4)	4.002 (5)	109.3 (2)
C32	F34	Cg4A^iv	3.663 (18)	4.31 (2)	110.3 (3)
N24	O25	Cg4ⁱⁱ	3.443 (9)	3.710 (5)	92.7 (5)
N24	O25	Cg4Aⁱⁱ	3.13 (2)	3.45 (2)	94.8 (6)
N24A	O25A	Cg4ⁱⁱ	3.41 (4)	4.19 (3)	126 (3)
N24A	O25A	Cg4Aⁱⁱ	3.10 (4)	3.91 (3)	128 (3)
S28	O30	Cg1ⁱⁱ	3.810 (3)	3.707 (2)	74.9 (1)
S28	O31	Cg1ⁱⁱ	3.529 (3)	3.707 (2)	85.6 (1)
S28	O31	Cg3ⁱⁱ	3.205 (3)	4.221 (2)	126.7 (1)

Symmetry codes: (ii) ; (iv) .

Notes: Cg represents the centroid of each ring, as follows: Cg1 ring C9/C11/C12/N10/C14/C13, Cg3 ring C5–C8/C13/C14, Cg4 ring C18–C23 and Cg4A ring C18A–C23A.

Table 3

π–π interactions (Å,°)

CgI	CgJ	Cg⋯Cg	Dihedral angle	Interplanar distance	Offset
1	2^v	3.547 (2)	3.4	3.504 (3)	0.556 (3)
2	2^v	3.981 (2)	0.0	3.504 (3)	1.891 (3)

Symmetry codes: (v) .

Notes: Cg represents the centroid of each ring, as follows: Cg1 ring C9/C11/C12/N10/C14/C13 and Cg2 ring C1–C4/C12/C11. Cg⋯Cg is the distance between ring centroids. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J.

7 in total

1. Stable and versatile active acridinium esters II.

Authors: Z Razavi; F McCapra
Journal: Luminescence Date: 2000 Jul-Aug Impact factor: 2.464

2. Stable and versatile active acridinium esters I.

Authors: Z Razavi; F McCapra
Journal: Luminescence Date: 2000 Jul-Aug Impact factor: 2.464

3. The double helix is dehydrated: evidence from the hydrolysis of acridinium ester-labeled probes.

Authors: M Becker; V Lerum; S Dickson; N C Nelson; E Matsuda
Journal: Biochemistry Date: 1999-04-27 Impact factor: 3.162

4. Dimorphism in (2Z)-2-benzylidene-N,7-dimethyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxamide.

Authors: B Sridhar; K Ravikumar; Y S Sadanandam
Journal: Acta Crystallogr C Date: 2006-11-22 Impact factor: 1.172

5. 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

6. Chemiluminescence quenching of pteroic acid-N-sulfonyl-acridinium-9-carboxamide conjugates by folate binding protein.

Authors: Maciej Adamczyk; James R Fino; Phillip G Mattingly; Jeffrey A Moore; You Pan
Journal: Bioorg Med Chem Lett Date: 2004-05-03 Impact factor: 2.823

7. 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