9-(2,6-Dibromo­phenoxy­carbonyl)-10-methyl­acridinium trifluoro­methane­sulfonate

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

doi:10.1107/S1600536805017952

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9-(2,6-Dibromophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate

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

In the title compound, C₂₁H₁₄Br₂NO₂⁺·CF₃O₃S⁻, adjacent cations are oriented either parallel or antiparallel. Together with the CF₃O₃S⁻ anions, the antiparallel-oriented cations form layers in which the ions are linked via a network of C—H

O (O from the anions) and π–π interactions (between the benzene rings). These layers, in turn, are linked via a network of five multidirectional π–π interactions between the acridine rings, and the crystal structure is stabilized by electrostatic interactions between the ions. The acridine and independent benzene rings are mutually oriented at an angle of 35.9 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017952/rz6089sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017952/rz6089Isup2.hkl Contains datablock I

CCDC reference: 277767

checkCIF report

Key indicators

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.009 Å
R factor = 0.046
wR factor = 0.123
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H4     ..  H26D    ..       1.72 Ang.
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H5     ..  H26A    ..       1.78 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Br25   -   C23     ..       5.80 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S27
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C31
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM-4 Software (Kuma Diffraction, 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).

9-(2,6-Dibromophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate top

Crystal data top

C₂₁H₁₄Br₂NO₂⁺·CF₃O₃S⁻	Z = 2
M_r = 621.21	F(000) = 612
Triclinic, P1	D_x = 1.869 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.414 (2) Å	Cell parameters from 50 reflections
b = 11.041 (2) Å	θ = 2.1–25.0°
c = 12.347 (2) Å	µ = 3.83 mm⁻¹
α = 105.83 (3)°	T = 290 K
β = 103.87 (3)°	Prism, yellow
γ = 107.40 (3)°	0.4 × 0.3 × 0.2 mm
V = 1103.7 (6) Å³

Data collection top

Kuma KM4 diffractometer	1691 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
θ/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.280, T_max = 0.465	l = 0→14
4059 measured reflections	3 standard reflections every 200 reflections
3860 independent reflections	intensity decay: 3.0%

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0687P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
3860 reflections	Δρ_max = 0.59 e Å⁻³
309 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (11)

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	Occ. (<1)
C1	0.0728 (6)	0.8038 (6)	0.5273 (5)	0.0356 (14)
H1	0.1605	0.7989	0.5072	0.043*
C2	0.0642 (8)	0.7963 (6)	0.6335 (5)	0.0443 (16)
H2	0.1439	0.7833	0.6844	0.053*
C3	−0.0681 (7)	0.8039 (6)	0.6667 (6)	0.0423 (15)
H3	−0.0732	0.7999	0.7400	0.051*
C4	−0.1884 (7)	0.8172 (6)	0.5919 (5)	0.0431 (16)
H4	−0.2735	0.8243	0.6152	0.052*
C5	−0.4131 (7)	0.8916 (6)	0.2332 (6)	0.0514 (17)
H5	−0.4970	0.8981	0.2583	0.062*
C6	−0.4029 (8)	0.9078 (7)	0.1302 (6)	0.0542 (18)
H6	−0.4739	0.9383	0.0908	0.065*
C7	−0.2829 (8)	0.8906 (7)	0.0883 (6)	0.0530 (17)
H7	−0.2893	0.8902	0.0118	0.064*
C8	−0.1687 (8)	0.8610 (6)	0.1509 (5)	0.0432 (15)
H8	−0.0861	0.8535	0.1244	0.052*
C9	−0.0505 (6)	0.8233 (6)	0.3345 (5)	0.0327 (13)
N10	−0.3046 (5)	0.8388 (5)	0.4052 (4)	0.0379 (12)
C11	−0.0496 (6)	0.8179 (5)	0.4481 (5)	0.0325 (14)
C12	−0.1836 (6)	0.8249 (6)	0.4817 (5)	0.0324 (13)
C13	−0.1713 (6)	0.8449 (6)	0.2622 (5)	0.0352 (14)
C14	−0.2975 (6)	0.8585 (5)	0.3009 (5)	0.0354 (14)
C15	0.0815 (7)	0.8046 (6)	0.2922 (5)	0.0330 (13)
O16	0.0220 (4)	0.6975 (4)	0.1885 (3)	0.0352 (9)
O17	0.2197 (5)	0.8733 (4)	0.3464 (4)	0.0489 (11)
C18	0.1277 (6)	0.6491 (5)	0.1441 (5)	0.0358 (14)
C19	0.1773 (7)	0.6845 (6)	0.0573 (5)	0.0412 (15)
C20	0.2626 (7)	0.6224 (7)	0.0050 (6)	0.0509 (17)
H20	0.2929	0.6445	−0.0558	0.061*
C21	0.2996 (8)	0.5247 (7)	0.0405 (6)	0.0564 (18)
H21	0.3556	0.4812	0.0034	0.068*
C22	0.2557 (7)	0.4911 (6)	0.1291 (6)	0.0520 (17)
H22	0.2828	0.4264	0.1543	0.062*
C23	0.1668 (7)	0.5521 (5)	0.1814 (5)	0.0336 (13)
Br24	0.13315 (9)	0.82219 (8)	0.01180 (7)	0.0651 (3)
Br25	0.10690 (10)	0.50960 (8)	0.30427 (7)	0.0682 (3)
C26	−0.4511 (7)	0.8276 (8)	0.4348 (6)	0.062 (2)
H26A	−0.5274	0.8345	0.3720	0.092*	0.50
H26B	−0.4253	0.9001	0.5093	0.092*	0.50
H26C	−0.4950	0.7410	0.4421	0.092*	0.50
H26D	−0.4377	0.8159	0.5103	0.092*	0.50
H26E	−0.5399	0.7503	0.3729	0.092*	0.50
H26F	−0.4701	0.9094	0.4402	0.092*	0.50
S27	0.47817 (19)	0.74668 (17)	0.74315 (14)	0.0462 (4)
O28	0.4471 (6)	0.7982 (5)	0.6488 (4)	0.0712 (14)
O29	0.6397 (5)	0.7615 (5)	0.7907 (4)	0.0647 (13)
O30	0.4055 (5)	0.7810 (5)	0.8293 (4)	0.0598 (13)
C31	0.3736 (9)	0.5637 (8)	0.6686 (7)	0.067 (2)
F32	0.4299 (7)	0.5121 (5)	0.5889 (5)	0.116 (2)
F33	0.3768 (6)	0.5002 (5)	0.7442 (5)	0.0994 (16)
F34	0.2197 (6)	0.5292 (5)	0.6071 (5)	0.0982 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.029 (3)	0.039 (4)	0.049 (4)	0.024 (3)	0.015 (3)	0.018 (3)
C2	0.052 (4)	0.039 (4)	0.037 (4)	0.023 (3)	0.003 (3)	0.012 (3)
C3	0.050 (4)	0.040 (4)	0.043 (4)	0.019 (3)	0.022 (3)	0.016 (3)
C4	0.041 (4)	0.043 (4)	0.050 (4)	0.018 (3)	0.024 (3)	0.015 (3)
C5	0.032 (3)	0.053 (4)	0.066 (5)	0.023 (3)	0.009 (3)	0.017 (4)
C6	0.047 (4)	0.050 (4)	0.063 (5)	0.024 (4)	0.007 (4)	0.023 (4)
C7	0.055 (4)	0.050 (4)	0.051 (4)	0.023 (4)	0.008 (4)	0.020 (4)
C8	0.048 (4)	0.045 (4)	0.039 (3)	0.024 (3)	0.012 (3)	0.017 (3)
C9	0.026 (3)	0.031 (3)	0.036 (3)	0.012 (3)	0.006 (3)	0.008 (3)
N10	0.028 (3)	0.037 (3)	0.049 (3)	0.016 (2)	0.016 (3)	0.009 (3)
C11	0.032 (3)	0.021 (3)	0.036 (4)	0.008 (3)	0.011 (3)	0.002 (3)
C12	0.026 (3)	0.033 (3)	0.030 (3)	0.009 (3)	0.007 (3)	0.005 (3)
C13	0.027 (3)	0.030 (4)	0.048 (4)	0.014 (3)	0.011 (3)	0.012 (3)
C14	0.020 (3)	0.021 (3)	0.049 (4)	0.005 (3)	0.002 (3)	0.003 (3)
C15	0.031 (4)	0.026 (3)	0.034 (3)	0.011 (3)	0.004 (3)	0.008 (3)
O16	0.025 (2)	0.037 (2)	0.044 (2)	0.0152 (19)	0.013 (2)	0.011 (2)
O17	0.026 (3)	0.052 (3)	0.057 (3)	0.014 (2)	0.010 (2)	0.007 (2)
C18	0.027 (3)	0.032 (4)	0.041 (4)	0.010 (3)	0.013 (3)	0.003 (3)
C19	0.036 (3)	0.038 (4)	0.047 (4)	0.013 (3)	0.014 (3)	0.014 (3)
C20	0.043 (4)	0.054 (4)	0.054 (4)	0.015 (4)	0.027 (4)	0.014 (4)
C21	0.041 (4)	0.043 (4)	0.067 (5)	0.013 (4)	0.017 (4)	0.000 (4)
C22	0.046 (4)	0.041 (4)	0.072 (5)	0.025 (4)	0.024 (4)	0.014 (4)
C23	0.041 (4)	0.022 (3)	0.031 (3)	0.007 (3)	0.011 (3)	0.009 (3)
Br24	0.0783 (6)	0.0685 (6)	0.0799 (6)	0.0395 (5)	0.0442 (5)	0.0470 (5)
Br25	0.0994 (7)	0.0650 (6)	0.0727 (6)	0.0481 (5)	0.0465 (5)	0.0411 (5)
C26	0.040 (4)	0.086 (6)	0.067 (5)	0.033 (4)	0.032 (4)	0.021 (4)
S27	0.0489 (11)	0.0536 (11)	0.0455 (9)	0.0265 (9)	0.0225 (9)	0.0197 (8)
O28	0.083 (4)	0.087 (4)	0.070 (3)	0.047 (3)	0.035 (3)	0.045 (3)
O29	0.042 (3)	0.076 (4)	0.069 (3)	0.024 (3)	0.016 (2)	0.018 (3)
O30	0.068 (3)	0.073 (3)	0.051 (3)	0.041 (3)	0.030 (3)	0.020 (3)
C31	0.046 (5)	0.063 (6)	0.071 (5)	0.012 (4)	0.016 (4)	0.009 (5)
F32	0.127 (4)	0.082 (4)	0.117 (4)	0.033 (3)	0.074 (4)	−0.013 (3)
F33	0.115 (4)	0.064 (3)	0.128 (4)	0.036 (3)	0.041 (3)	0.050 (3)
F34	0.066 (3)	0.103 (4)	0.090 (4)	0.015 (3)	0.017 (3)	0.014 (3)

Geometric parameters (Å, º) top

C1—C2	1.355 (8)	C15—O17	1.196 (6)
C1—C11	1.400 (7)	O16—C18	1.413 (6)
C1—H1	0.9300	C18—C19	1.371 (8)
C2—C3	1.419 (8)	C18—C23	1.385 (8)
C2—H2	0.9306	C19—C20	1.367 (8)
C3—C4	1.353 (8)	C19—Br24	1.879 (6)
C3—H3	0.9300	C20—C21	1.373 (9)
C4—C12	1.397 (8)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.362 (9)
C5—C6	1.354 (9)	C21—H21	0.9300
C5—C14	1.409 (8)	C22—C23	1.389 (8)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.391 (9)	C23—Br25	1.865 (5)
C6—H6	0.9300	C26—H26A	0.9600
C7—C8	1.345 (8)	C26—H26B	0.9600
C7—H7	0.9300	C26—H26C	0.9600
C8—C13	1.438 (8)	C26—H26D	0.9600
C8—H8	0.9300	C26—H26E	0.9600
C9—C13	1.393 (7)	C26—H26F	0.9600
C9—C11	1.417 (7)	S27—O30	1.424 (4)
C9—C15	1.505 (8)	S27—O29	1.433 (5)
N10—C12	1.371 (7)	S27—O28	1.437 (5)
N10—C14	1.376 (7)	S27—C31	1.805 (8)
N10—C26	1.488 (7)	C31—F32	1.303 (8)
C11—C12	1.436 (7)	C31—F33	1.311 (9)
C13—C14	1.415 (8)	C31—F34	1.344 (9)
C15—O16	1.336 (7)

C2—C1—C11	120.4 (5)	C20—C19—C18	120.4 (6)
C2—C1—H1	119.5	C20—C19—Br24	119.3 (5)
C11—C1—H1	120.1	C18—C19—Br24	120.3 (4)
C1—C2—C3	120.7 (6)	C19—C20—C21	119.6 (6)
C1—C2—H2	120.0	C19—C20—H20	120.1
C3—C2—H2	119.2	C21—C20—H20	120.2
C4—C3—C2	120.3 (6)	C22—C21—C20	120.9 (6)
C4—C3—H3	119.2	C22—C21—H21	119.8
C2—C3—H3	120.6	C20—C21—H21	119.4
C3—C4—C12	120.6 (5)	C21—C22—C23	119.9 (6)
C3—C4—H4	119.7	C21—C22—H22	120.8
C12—C4—H4	119.7	C23—C22—H22	119.3
C6—C5—C14	119.1 (6)	C18—C23—C22	119.1 (5)
C6—C5—H5	121.4	C18—C23—Br25	120.1 (4)
C14—C5—H5	119.5	C22—C23—Br25	120.8 (5)
C5—C6—C7	121.8 (6)	N10—C26—H26A	109.5
C5—C6—H6	117.9	N10—C26—H26B	109.5
C7—C6—H6	120.1	H26A—C26—H26B	109.5
C8—C7—C6	121.2 (6)	N10—C26—H26C	109.5
C8—C7—H7	120.0	H26A—C26—H26C	109.5
C6—C7—H7	118.5	H26B—C26—H26C	109.5
C7—C8—C13	119.7 (6)	N10—C26—H26D	109.5
C7—C8—H8	120.9	H26A—C26—H26D	141.1
C13—C8—H8	119.4	H26B—C26—H26D	56.3
C13—C9—C11	121.1 (5)	H26C—C26—H26D	56.3
C13—C9—C15	120.0 (5)	N10—C26—H26E	109.5
C11—C9—C15	119.0 (5)	H26A—C26—H26E	56.3
C12—N10—C14	122.6 (4)	H26B—C26—H26E	141.1
C12—N10—C26	118.3 (5)	H26C—C26—H26E	56.3
C14—N10—C26	119.0 (5)	H26D—C26—H26E	109.5
C1—C11—C9	123.6 (5)	N10—C26—H26F	109.5
C1—C11—C12	118.8 (5)	H26A—C26—H26F	56.3
C9—C11—C12	117.6 (5)	H26B—C26—H26F	56.3
N10—C12—C4	121.2 (5)	H26C—C26—H26F	141.1
N10—C12—C11	119.6 (5)	H26D—C26—H26F	109.5
C4—C12—C11	119.3 (5)	H26E—C26—H26F	109.5
C9—C13—C14	119.7 (5)	O30—S27—O29	115.9 (3)
C9—C13—C8	122.1 (5)	O30—S27—O28	114.1 (3)
C14—C13—C8	118.2 (5)	O29—S27—O28	114.5 (3)
N10—C14—C5	121.1 (5)	O30—S27—C31	103.3 (3)
N10—C14—C13	118.8 (5)	O29—S27—C31	102.5 (3)
C5—C14—C13	120.1 (6)	O28—S27—C31	104.2 (4)
C9—C15—O16	110.1 (5)	F32—C31—F33	108.5 (7)
C9—C15—O17	124.5 (5)	F32—C31—F34	105.1 (7)
C15—O16—C18	118.7 (4)	F33—C31—F34	106.6 (7)
O16—C15—O17	125.4 (5)	F32—C31—S27	112.2 (6)
C19—C18—C23	120.1 (5)	F33—C31—S27	112.4 (6)
C19—C18—O16	121.8 (5)	F34—C31—S27	111.6 (6)
C23—C18—O16	117.7 (5)

C11—C1—C2—C3	−0.6 (9)	C8—C13—C14—N10	177.8 (5)
C1—C2—C3—C4	0.8 (9)	C9—C13—C14—C5	174.8 (5)
C2—C3—C4—C12	−0.6 (9)	C8—C13—C14—C5	−2.2 (8)
C14—C5—C6—C7	1.0 (10)	C13—C9—C15—O17	123.5 (6)
C5—C6—C7—C8	−2.0 (11)	C13—C9—C15—O16	−58.9 (6)
C6—C7—C8—C13	0.8 (10)	C11—C9—C15—O16	120.9 (5)
C2—C1—C11—C9	−178.5 (6)	O17—C15—O16—C18	8.0 (8)
C2—C1—C11—C12	0.3 (8)	C9—C15—O16—C18	−169.6 (5)
C13—C9—C11—C1	−176.4 (5)	C11—C9—C15—O17	−56.7 (8)
C15—C9—C11—C1	3.8 (8)	C15—O16—C18—C19	−98.7 (6)
C13—C9—C11—C12	4.7 (8)	C15—O16—C18—C23	88.3 (6)
C15—C9—C11—C12	−175.1 (5)	C23—C18—C19—C20	1.4 (9)
C14—N10—C12—C4	174.3 (5)	O16—C18—C19—C20	−171.4 (5)
C26—N10—C12—C4	−7.7 (8)	C23—C18—C19—Br24	−177.0 (4)
C14—N10—C12—C11	−5.9 (8)	O16—C18—C19—Br24	10.2 (8)
C26—N10—C12—C11	172.2 (5)	C18—C19—C20—C21	−0.5 (9)
C3—C4—C12—N10	−179.8 (6)	Br24—C19—C20—C21	178.0 (5)
C3—C4—C12—C11	0.4 (9)	C19—C20—C21—C22	−1.6 (10)
C1—C11—C12—N10	180.0 (5)	C20—C21—C22—C23	2.6 (10)
C9—C11—C12—N10	−1.1 (8)	C19—C18—C23—C22	−0.4 (9)
C1—C11—C12—C4	−0.2 (8)	O16—C18—C23—C22	172.8 (5)
C9—C11—C12—C4	178.7 (5)	C19—C18—C23—Br25	177.3 (4)
C11—C9—C13—C14	−1.6 (8)	O16—C18—C23—Br25	−9.6 (7)
C15—C9—C13—C14	178.2 (5)	C21—C22—C23—C18	−1.6 (9)
C11—C9—C13—C8	175.3 (5)	C21—C22—C23—Br25	−179.3 (5)
C15—C9—C13—C8	−5.0 (8)	O30—S27—C31—F32	−177.0 (6)
C7—C8—C13—C9	−175.7 (6)	O29—S27—C31—F32	−56.2 (7)
C7—C8—C13—C14	1.2 (9)	O28—S27—C31—F32	63.5 (7)
C12—N10—C14—C5	−170.9 (5)	O30—S27—C31—F33	−54.4 (6)
C26—N10—C14—C5	11.1 (8)	O29—S27—C31—F33	66.4 (6)
C12—N10—C14—C13	9.1 (8)	O28—S27—C31—F33	−174.0 (5)
C26—N10—C14—C13	−168.9 (5)	O30—S27—C31—F34	65.3 (6)
C6—C5—C14—N10	−178.9 (6)	O29—S27—C31—F34	−173.9 (6)
C6—C5—C14—C13	1.1 (9)	O28—S27—C31—F34	−54.2 (6)
C9—C13—C14—N10	−5.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O29ⁱ	0.93	2.52	3.362 (8)	150
C20—H20···O30ⁱⁱ	0.93	2.52	3.413 (8)	161
C22—H22···O29ⁱⁱⁱ	0.93	2.59	3.523 (9)	176

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

π–π interactions (Å,°) in (I) top

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar dist.	Offset
1	1^iv	3.968 (3)	0.0	3.515 (4)	1.841 (4)
1	2^iv	3.610 (4)	2.1	3.468 (4)	1.003 (4)
2	1^iv	3.610 (4)	2.1	3.458 (4)	1.037 (4)
2	3^iv	3.836 (4)	7.1	3.500 (4)	1.570 (4)
3	2^iv	3.835 (4)	7.1	3.281 (4)	1.986 (4)
4	4^v	3.719 (4)	0.0	3.462 (4)	1.358 (4)

Symmetry codes: (iv) -x, 2-y, 1-z; (v) -x, 1-y, -z.

Cg represents the centre of gravity of the rings, as follows: Cg1 ring C9/C11/C12/N10/C14/C13, Cg2 ring C1–C4/C12/C11, Cg3 ring C5–C8/C13/C14 and Cg4 ring C18–C23.

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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