2,6-Diiodo­phenyl acridine-9-carboxyl­ate

Sikorski, A.; Krzymiński, K.; Białońska, A.; Lis, T.; Błażejowski*, J.

doi:10.1107/S1600536805038729

2,6-Diiodophenyl acridine-9-carboxylate

A. Sikorski, K. Krzymiński, A. Białońska, T. Lis and J. Błażejowski

In the orthorhombic crystalline phase of the title compound, C₂₀H₁₁I₂NO₂, all the benzene rings are parallel, whereas the acridine systems are either parallel or perpendicular to each other; this generates a herring-bone pattern. The acridine systems and benzene rings are inclined at an angle of 45.5 (1)° to each other, and the acridine systems and carboxylate groups are inclined at an angle of 54.2 (1)°. Oppositely oriented consecutive molecules, with π–π interactions between their acridine systems and I

I and I

N contacts, are aligned in stacks along the a axis. These stacks, interacting through π–π contacts between benzene rings, are arranged in layers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038729/cf2003sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038729/cf2003Isup2.hkl Contains datablock I

CCDC reference: 293848

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.007 Å
R factor = 0.038
wR factor = 0.095
Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.92
PLAT213_ALERT_2_C Atom C19     has ADP max/min Ratio .............       3.30 prolat

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

Computing details top

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).

2,5-diiodophenyl acridine-9-carboxylate top

Crystal data top

C₂₀H₁₁I₂NO₂	F(000) = 2080
M_r = 551.10	D_x = 2.065 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15550 reflections
a = 9.297 (3) Å	θ = 3.1–27.8°
b = 15.673 (5) Å	µ = 3.56 mm⁻¹
c = 24.329 (9) Å	T = 100 K
V = 3545 (2) Å³	Plate, yellow
Z = 8	0.50 × 0.40 × 0.08 mm

Data collection top

Kuma KM-4-CCD diffractometer	4128 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 27.8°, θ_min = 3.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	h = −12→11
T_min = 0.194, T_max = 0.752	k = −20→20
24568 measured reflections	l = −31→28

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0484P)²] where P = (F_o² + 2F_c²)/3
4128 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 2.10 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

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.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.4245 (4)	0.2819 (3)	0.3176 (2)	0.0255 (11)
H1	0.4139	0.2920	0.3558	0.031*
C2	0.3432 (5)	0.3252 (3)	0.2814 (2)	0.0262 (11)
H2	0.2743	0.3650	0.2947	0.031*
C3	0.3578 (5)	0.3130 (3)	0.2240 (2)	0.0277 (12)
H3	0.2994	0.3447	0.1994	0.033*
C4	0.4541 (5)	0.2566 (3)	0.2042 (2)	0.0257 (11)
H4	0.4635	0.2494	0.1656	0.031*
C5	0.8137 (5)	0.0440 (3)	0.2280 (2)	0.0252 (11)
H5	0.8194	0.0397	0.1891	0.030*
C6	0.8995 (4)	−0.0056 (3)	0.2602 (2)	0.0277 (11)
H6	0.9643	−0.0447	0.2436	0.033*
C7	0.8932 (5)	0.0002 (3)	0.3178 (2)	0.0278 (12)
H7	0.9547	−0.0345	0.3396	0.033*
C8	0.8003 (4)	0.0549 (3)	0.3429 (2)	0.0249 (11)
H8	0.7970	0.0578	0.3819	0.030*
C9	0.6118 (4)	0.1692 (3)	0.33342 (19)	0.0204 (10)
N10	0.6349 (3)	0.1505 (2)	0.21782 (17)	0.0230 (9)
C11	0.5279 (4)	0.2201 (3)	0.2985 (2)	0.0217 (11)
C12	0.5424 (5)	0.2071 (3)	0.2406 (2)	0.0229 (10)
C13	0.7072 (5)	0.1083 (3)	0.3108 (2)	0.0237 (10)
C14	0.7151 (5)	0.1028 (3)	0.2526 (2)	0.0228 (10)
C15	0.6008 (4)	0.1837 (3)	0.3937 (2)	0.0220 (10)
O16	0.5719 (3)	0.10875 (18)	0.42094 (13)	0.0212 (7)
O17	0.6092 (3)	0.25119 (19)	0.41681 (14)	0.0285 (8)
C18	0.5311 (5)	0.1136 (3)	0.4762 (2)	0.0243 (10)
C19	0.6310 (5)	0.1125 (3)	0.5176 (2)	0.0260 (11)
C20	0.5849 (6)	0.1054 (3)	0.5718 (2)	0.0335 (12)
H20	0.6540	0.1023	0.6005	0.040*
C21	0.4411 (6)	0.1027 (3)	0.5843 (2)	0.0325 (12)
H21	0.4118	0.0969	0.6216	0.039*
C22	0.3381 (6)	0.1082 (3)	0.5431 (2)	0.0318 (12)
H22	0.2384	0.1073	0.5518	0.038*
C23	0.3842 (5)	0.1152 (3)	0.4887 (2)	0.0239 (11)
I24	0.85223 (3)	0.11763 (2)	0.501604 (16)	0.03345 (12)
I25	0.23482 (3)	0.128043 (19)	0.424114 (15)	0.03119 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.017 (2)	0.017 (2)	0.042 (3)	−0.0030 (18)	0.006 (2)	0.001 (2)
C2	0.018 (2)	0.019 (2)	0.041 (3)	−0.0020 (18)	−0.001 (2)	0.004 (2)
C3	0.021 (2)	0.020 (3)	0.042 (3)	−0.0044 (19)	−0.005 (2)	0.008 (2)
C4	0.022 (2)	0.023 (2)	0.032 (3)	−0.0068 (19)	−0.001 (2)	0.008 (2)
C5	0.022 (2)	0.021 (2)	0.032 (3)	−0.0058 (19)	0.001 (2)	−0.005 (2)
C6	0.022 (2)	0.018 (2)	0.044 (3)	−0.0031 (19)	0.005 (2)	−0.004 (2)
C7	0.022 (2)	0.021 (3)	0.040 (3)	0.0033 (18)	0.000 (2)	0.003 (2)
C8	0.018 (2)	0.021 (2)	0.036 (3)	−0.0039 (18)	0.000 (2)	0.000 (2)
C9	0.012 (2)	0.021 (2)	0.027 (3)	−0.0027 (17)	0.0015 (18)	0.002 (2)
N10	0.0155 (18)	0.0202 (19)	0.033 (2)	−0.0072 (15)	0.0006 (17)	0.0040 (18)
C11	0.014 (2)	0.014 (2)	0.037 (3)	−0.0044 (16)	−0.0020 (19)	0.001 (2)
C12	0.018 (2)	0.018 (2)	0.033 (3)	−0.0043 (18)	0.001 (2)	0.001 (2)
C13	0.014 (2)	0.020 (2)	0.037 (3)	−0.0057 (17)	0.000 (2)	0.001 (2)
C14	0.016 (2)	0.019 (2)	0.033 (3)	−0.0066 (18)	0.006 (2)	0.001 (2)
C15	0.012 (2)	0.021 (2)	0.033 (3)	0.0000 (17)	0.0023 (19)	0.003 (2)
O16	0.0197 (15)	0.0210 (16)	0.0230 (19)	−0.0020 (12)	0.0016 (13)	−0.0001 (14)
O17	0.0261 (17)	0.0220 (18)	0.038 (2)	−0.0023 (13)	−0.0003 (15)	−0.0031 (16)
C18	0.024 (2)	0.017 (2)	0.032 (3)	−0.0038 (18)	0.005 (2)	0.001 (2)
C19	0.021 (2)	0.026 (3)	0.030 (3)	−0.0019 (18)	−0.001 (2)	−0.023 (2)
C20	0.043 (3)	0.027 (3)	0.030 (3)	−0.004 (2)	−0.002 (2)	−0.004 (2)
C21	0.043 (3)	0.030 (3)	0.025 (3)	−0.003 (2)	0.003 (2)	−0.010 (2)
C22	0.032 (3)	0.025 (3)	0.038 (3)	0.000 (2)	0.017 (2)	−0.008 (2)
C23	0.022 (2)	0.018 (2)	0.032 (3)	0.0008 (17)	0.0047 (19)	−0.006 (2)
I24	0.02268 (17)	0.0368 (2)	0.0409 (2)	−0.00353 (13)	−0.00691 (14)	0.00059 (18)
I25	0.01820 (16)	0.03018 (19)	0.0452 (2)	0.00071 (12)	−0.00057 (14)	0.00198 (16)

Geometric parameters (Å, º) top

C1—C2	1.344 (6)	C9—C15	1.488 (6)
C1—C11	1.441 (6)	N10—C12	1.353 (6)
C1—H1	0.950	N10—C14	1.354 (6)
C2—C3	1.416 (7)	C11—C12	1.430 (6)
C2—H2	0.950	C13—C14	1.420 (7)
C3—C4	1.347 (6)	C15—O16	1.375 (5)
C3—H3	0.950	C15—O17	1.200 (5)
C4—C12	1.435 (6)	O16—C18	1.399 (6)
C4—H4	0.950	C18—C19	1.370 (7)
C5—C6	1.362 (7)	C18—C23	1.399 (6)
C5—C14	1.431 (6)	C19—C20	1.389 (7)
C5—H5	0.950	C19—I24	2.095 (5)
C6—C7	1.406 (7)	C20—C21	1.372 (7)
C6—H6	0.950	C20—H20	0.950
C7—C8	1.362 (6)	C21—C22	1.390 (7)
C7—H7	0.950	C21—H21	0.950
C8—C13	1.435 (6)	C22—C23	1.396 (7)
C8—H8	0.950	C22—H22	0.950
C9—C11	1.404 (6)	C23—I25	2.107 (5)
C9—C13	1.414 (6)

C2—C1—C11	120.3 (5)	N10—C12—C11	123.8 (4)
C2—C1—H1	119.9	N10—C12—C4	117.8 (4)
C11—C1—H1	119.9	C11—C12—C4	118.4 (4)
C1—C2—C3	121.5 (5)	C9—C13—C14	117.5 (4)
C1—C2—H2	119.3	C9—C13—C8	124.1 (5)
C3—C2—H2	119.3	C14—C13—C8	118.4 (4)
C4—C3—C2	120.4 (5)	N10—C14—C13	124.2 (4)
C4—C3—H3	119.8	N10—C14—C5	116.5 (5)
C2—C3—H3	119.8	C13—C14—C5	119.3 (4)
C3—C4—C12	121.0 (5)	O17—C15—O16	122.7 (4)
C3—C4—H4	119.5	C9—C15—O17	126.3 (4)
C12—C4—H4	119.5	C9—C15—O16	111.0 (4)
C6—C5—C14	120.1 (5)	C15—O16—C18	118.0 (3)
C6—C5—H5	119.9	C19—C18—C23	120.1 (5)
C14—C5—H5	119.9	C19—C18—O16	121.5 (4)
C5—C6—C7	120.8 (5)	C23—C18—O16	118.3 (4)
C5—C6—H6	119.6	C18—C19—C20	119.3 (5)
C7—C6—H6	119.6	C18—C19—I24	121.9 (4)
C8—C7—C6	120.9 (5)	C20—C19—I24	118.8 (4)
C8—C7—H7	119.5	C21—C20—C19	120.9 (5)
C6—C7—H7	119.5	C21—C20—H20	119.5
C7—C8—C13	120.4 (5)	C19—C20—H20	119.5
C7—C8—H8	119.8	C20—C21—C22	120.6 (5)
C13—C8—H8	119.8	C20—C21—H21	119.7
C11—C9—C13	119.8 (4)	C22—C21—H21	119.7
C11—C9—C15	118.2 (4)	C21—C22—C23	118.5 (5)
C13—C9—C15	122.0 (4)	C21—C22—H22	120.7
C12—N10—C14	117.1 (4)	C23—C22—H22	120.7
C9—C11—C12	117.6 (4)	C22—C23—C18	120.3 (5)
C9—C11—C1	123.9 (5)	C22—C23—I25	120.8 (4)
C12—C11—C1	118.5 (4)	C18—C23—I25	118.9 (4)

C11—C1—C2—C3	−1.1 (6)	C9—C13—C14—N10	−1.6 (6)
C1—C2—C3—C4	0.4 (7)	C8—C13—C14—N10	−178.9 (4)
C2—C3—C4—C12	0.7 (6)	C9—C13—C14—C5	177.9 (4)
C14—C5—C6—C7	−0.3 (7)	C8—C13—C14—C5	0.6 (6)
C5—C6—C7—C8	0.7 (7)	C6—C5—C14—N10	179.2 (4)
C6—C7—C8—C13	−0.4 (7)	C6—C5—C14—C13	−0.3 (6)
C13—C9—C11—C12	0.5 (6)	C11—C9—C15—O17	−49.6 (6)
C15—C9—C11—C12	178.3 (4)	C13—C9—C15—O17	128.2 (5)
C13—C9—C11—C1	178.0 (4)	C11—C9—C15—O16	127.4 (4)
C15—C9—C11—C1	−4.2 (6)	C13—C9—C15—O16	−54.8 (5)
C2—C1—C11—C9	−176.7 (4)	O17—C15—O16—C18	9.2 (6)
C2—C1—C11—C12	0.7 (6)	C9—C15—O16—C18	−168.0 (3)
C14—N10—C12—C11	1.5 (6)	C15—O16—C18—C19	−89.1 (5)
C14—N10—C12—C4	−178.4 (4)	C15—O16—C18—C23	94.2 (5)
C9—C11—C12—N10	−1.9 (6)	C23—C18—C19—C20	5.6 (7)
C1—C11—C12—N10	−179.5 (4)	O16—C18—C19—C20	−171.0 (4)
C9—C11—C12—C4	178.0 (4)	C23—C18—C19—I24	−176.2 (3)
C1—C11—C12—C4	0.4 (6)	O16—C18—C19—I24	7.2 (6)
C3—C4—C12—N10	178.8 (4)	C18—C19—C20—C21	−2.4 (7)
C3—C4—C12—C11	−1.1 (6)	I24—C19—C20—C21	179.3 (4)
C11—C9—C13—C14	1.1 (6)	C19—C20—C21—C22	−0.9 (7)
C15—C9—C13—C14	−176.6 (4)	C20—C21—C22—C23	1.0 (7)
C11—C9—C13—C8	178.3 (4)	C21—C22—C23—C18	2.2 (6)
C15—C9—C13—C8	0.5 (7)	C21—C22—C23—I25	−178.0 (3)
C7—C8—C13—C9	−177.4 (4)	C19—C18—C23—C22	−5.6 (7)
C7—C8—C13—C14	−0.2 (6)	O16—C18—C23—C22	171.2 (4)
C12—N10—C14—C13	0.3 (6)	C19—C18—C23—I25	174.6 (3)
C12—N10—C14—C5	−179.2 (4)	O16—C18—C23—I25	−8.7 (5)

Table 2. π–π interactions (Å,°). Cg represents the centroids 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 and Cg4 ring C18/C19/C20/C21/C22/C23 (Fig. 1). top

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar dist.	Offset
1	2ⁱ	3.522 (3)	3.5	3.243 (3)	1.374 (3)
1	3ⁱⁱ	3.725 (3)	2.3	3.312 (3)	1.705 (3)
2	1ⁱⁱ	3.522 (3)	3.5	3.319 (3)	1.178 (3)
2	3ⁱⁱ	3.796 (3)	2.6	3.322 (3)	1.837 (3)
3	1ⁱ	3.725 (2)	2.3	3.290 (3)	1.747 (3)
3	2ⁱ	3.797 (3)	2.6	3.279 (3)	1.915 (3)
4	4ⁱⁱⁱ	3.748 (3)	0.0	3.531 (3)	1.257 (3)

Notes: 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. Symmetry codes: (i) 1/2+x, y, 1/2-z; (ii) -1/2+x, y, 1/2-z; (iii) 1-x, -y, 1-z.

I···I and N···I contacts (Å, °) in (I). top

X	I	J	I···J	X-I···J
C19	I24	I25^iv	4.029 (5)	162.8 (2)
C23	I25	I24^v	4.029 (5)	103.3 (2)
C23	I25	N10ⁱⁱ	3.593 (4)	153.7 (2)

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

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2,6-Diiodo­phenyl acridine-9-carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

2,6-Diiodophenyl acridine-9-carboxylate