2,6-Dimethyl-phenyl acridine-9-carboxyl-ate.

In the title compound, C(22)H(17)NO(2), the acridine ring system and the benzene ring are oriented at a dihedral angle of 37.7 (1)°. The carboxyl group is twisted at an angle of 67.7 (1)° relative to the acridine skeleton. In the crystal, mol-ecules are arranged in stacks along the b axis, with all of the acridine rings involved in multiple π-π inter-actions [centroid-centroid distances in the range 3.632 (2)-4.101 (2) Å]. The acridine moieties are parallel within the stacks, but inclined at an angle of 52.7 (1)° in adjacent stacks.

Related literature

For general background, see: Krzymiński et al. (2011 ▶); Natrajan et al. (2012 ▶). For related structures, see: Sikorski et al. (2005 ▶); Sikorski et al. (2006 ▶). For inter­molecular inter­actions, see: Hunter et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Sikorski et al. (2005 ▶).

Experimental

Crystal data

C22H17NO2

M = 327.37

Monoclinic,

a = 12.8617 (10) Å

b = 7.5352 (5) Å

c = 17.5950 (15) Å

β = 103.143 (8)°

V = 1660.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.45 × 0.12 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.349, T max = 1.000

10387 measured reflections

2913 independent reflections

1908 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.151

S = 0.97

2913 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681205129X/ng5313sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205129X/ng5313Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205129X/ng5313Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H17NO2	F(000) = 688
Mr = 327.37	Dx = 1.313 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2738 reflections
a = 12.8617 (10) Å	θ = 3.5–29.2°
b = 7.5352 (5) Å	µ = 0.08 mm−1
c = 17.5950 (15) Å	T = 295 K
β = 103.143 (8)°	Needle, light-yellow
V = 1660.6 (2) Å3	0.45 × 0.12 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2913 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1908 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 10.4002 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −15→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→8
Tmin = 0.349, Tmax = 1.000	l = −18→20
10387 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
2913 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.24 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	Uiso*/Ueq
C1	0.48802 (17)	0.9058 (3)	0.16670 (14)	0.0453 (6)
H1	0.4347	0.9142	0.1944	0.054*
C2	0.58693 (18)	0.9693 (3)	0.19883 (15)	0.0528 (6)
H2	0.6007	1.0210	0.2481	0.063*
C3	0.66912 (19)	0.9573 (3)	0.15763 (17)	0.0551 (7)
H3	0.7365	1.0021	0.1800	0.066*
C4	0.65119 (18)	0.8819 (3)	0.08637 (16)	0.0516 (6)
H4	0.7064	0.8749	0.0603	0.062*
C5	0.4238 (2)	0.5983 (3)	−0.12990 (15)	0.0544 (6)
H5	0.4820	0.5880	−0.1528	0.065*
C6	0.3282 (2)	0.5381 (3)	−0.16823 (15)	0.0611 (7)
H6	0.3209	0.4867	−0.2172	0.073*
C7	0.2385 (2)	0.5519 (3)	−0.13491 (15)	0.0589 (7)
H7	0.1724	0.5106	−0.1624	0.071*
C8	0.24756 (19)	0.6245 (3)	−0.06369 (15)	0.0512 (6)
H8	0.1878	0.6314	−0.0424	0.061*
C9	0.36337 (16)	0.7668 (3)	0.05347 (12)	0.0373 (5)
N10	0.53517 (15)	0.7388 (2)	−0.02047 (12)	0.0463 (5)
C11	0.46450 (16)	0.8267 (3)	0.09145 (13)	0.0376 (5)
C12	0.54857 (17)	0.8128 (3)	0.05037 (14)	0.0418 (6)
C13	0.34688 (17)	0.6905 (3)	−0.02074 (13)	0.0396 (5)
C14	0.43823 (19)	0.6776 (3)	−0.05490 (13)	0.0428 (6)
C15	0.27353 (16)	0.7908 (3)	0.09379 (14)	0.0385 (5)
O16	0.20166 (11)	0.91069 (18)	0.05648 (8)	0.0418 (4)
O17	0.26699 (12)	0.7193 (2)	0.15308 (10)	0.0545 (5)
C18	0.12755 (16)	0.9763 (3)	0.09855 (13)	0.0404 (5)
C19	0.03752 (17)	0.8771 (3)	0.10077 (14)	0.0496 (6)
C20	−0.03222 (19)	0.9513 (4)	0.14183 (16)	0.0664 (8)
H20	−0.0937	0.8897	0.1450	0.080*
C21	−0.0124 (2)	1.1126 (4)	0.17756 (17)	0.0708 (8)
H21A	−0.0595	1.1581	0.2056	0.085*
C22	0.0764 (2)	1.2077 (3)	0.17229 (16)	0.0637 (7)
H22	0.0883	1.3183	0.1961	0.076*
C23	0.14931 (17)	1.1414 (3)	0.13174 (14)	0.0478 (6)
C24	0.0152 (2)	0.7020 (3)	0.06043 (18)	0.0698 (8)
H24A	−0.0550	0.6625	0.0629	0.105*
H24B	0.0671	0.6166	0.0857	0.105*
H24C	0.0190	0.7143	0.0068	0.105*
C25	0.2463 (2)	1.2462 (3)	0.12474 (17)	0.0655 (8)
H25A	0.2471	1.3573	0.1516	0.098*
H25B	0.2442	1.2680	0.0706	0.098*
H25C	0.3096	1.1802	0.1475	0.098*

	U11	U22	U33	U12	U13	U23
C1	0.0440 (13)	0.0553 (13)	0.0372 (14)	−0.0005 (11)	0.0104 (11)	−0.0009 (11)
C2	0.0547 (15)	0.0593 (14)	0.0411 (15)	−0.0042 (12)	0.0038 (13)	−0.0002 (12)
C3	0.0416 (13)	0.0585 (15)	0.0618 (19)	−0.0061 (11)	0.0048 (13)	0.0081 (13)
C4	0.0423 (13)	0.0536 (14)	0.0609 (18)	0.0029 (11)	0.0161 (13)	0.0124 (13)
C5	0.0751 (18)	0.0502 (13)	0.0443 (16)	0.0070 (13)	0.0270 (14)	−0.0008 (12)
C6	0.094 (2)	0.0537 (15)	0.0386 (16)	0.0000 (14)	0.0217 (16)	−0.0054 (12)
C7	0.0680 (17)	0.0592 (15)	0.0452 (17)	−0.0065 (12)	0.0039 (14)	−0.0080 (13)
C8	0.0550 (14)	0.0552 (14)	0.0435 (16)	−0.0017 (12)	0.0114 (12)	−0.0056 (12)
C9	0.0416 (13)	0.0384 (11)	0.0332 (13)	0.0032 (9)	0.0113 (10)	0.0033 (10)
N10	0.0515 (12)	0.0487 (11)	0.0426 (13)	0.0089 (9)	0.0189 (10)	0.0079 (9)
C11	0.0399 (12)	0.0414 (11)	0.0313 (13)	0.0025 (10)	0.0079 (10)	0.0058 (10)
C12	0.0441 (13)	0.0428 (12)	0.0401 (15)	0.0065 (10)	0.0130 (11)	0.0117 (11)
C13	0.0471 (13)	0.0381 (11)	0.0340 (13)	0.0042 (10)	0.0100 (11)	0.0035 (10)
C14	0.0548 (14)	0.0415 (12)	0.0346 (14)	0.0086 (11)	0.0154 (11)	0.0057 (10)
C15	0.0395 (12)	0.0421 (12)	0.0336 (14)	0.0000 (10)	0.0073 (10)	0.0014 (10)
O16	0.0417 (8)	0.0498 (8)	0.0358 (9)	0.0086 (7)	0.0126 (7)	0.0059 (7)
O17	0.0548 (10)	0.0681 (10)	0.0449 (11)	0.0129 (8)	0.0204 (8)	0.0177 (9)
C18	0.0384 (12)	0.0497 (13)	0.0331 (13)	0.0104 (10)	0.0083 (10)	0.0045 (10)
C19	0.0388 (13)	0.0628 (15)	0.0465 (16)	0.0048 (11)	0.0078 (11)	0.0052 (12)
C20	0.0425 (15)	0.094 (2)	0.066 (2)	0.0067 (14)	0.0189 (14)	0.0087 (17)
C21	0.0607 (17)	0.096 (2)	0.063 (2)	0.0278 (17)	0.0275 (15)	0.0028 (17)
C22	0.0748 (18)	0.0632 (16)	0.0539 (18)	0.0194 (14)	0.0165 (15)	−0.0042 (13)
C23	0.0513 (14)	0.0520 (14)	0.0402 (15)	0.0098 (11)	0.0104 (12)	0.0049 (11)
C24	0.0542 (16)	0.0745 (17)	0.079 (2)	−0.0130 (14)	0.0115 (15)	−0.0051 (16)
C25	0.0749 (18)	0.0547 (14)	0.0677 (19)	−0.0089 (13)	0.0177 (16)	−0.0063 (14)

C1—C2	1.356 (3)	C11—C12	1.435 (3)
C1—C11	1.420 (3)	C13—C14	1.440 (3)
C1—H1	0.9300	C15—O17	1.194 (2)
C2—C3	1.414 (3)	C15—O16	1.351 (2)
C2—H2	0.9300	O16—C18	1.422 (2)
C3—C4	1.348 (3)	C18—C23	1.376 (3)
C3—H3	0.9300	C18—C19	1.386 (3)
C4—C12	1.426 (3)	C19—C20	1.391 (3)
C4—H4	0.9300	C19—C24	1.495 (3)
C5—C6	1.340 (3)	C20—C21	1.366 (4)
C5—C14	1.422 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.370 (4)
C6—C7	1.412 (4)	C21—H21A	0.9300
C6—H6	0.9300	C22—C23	1.394 (3)
C7—C8	1.348 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—C25	1.505 (3)
C8—C13	1.418 (3)	C24—H24A	0.9600
C8—H8	0.9300	C24—H24B	0.9600
C9—C11	1.395 (3)	C24—H24C	0.9600
C9—C13	1.398 (3)	C25—H25A	0.9600
C9—C15	1.498 (3)	C25—H25B	0.9600
N10—C14	1.338 (3)	C25—H25C	0.9600
N10—C12	1.340 (3)
C2—C1—C11	121.2 (2)	N10—C14—C5	118.4 (2)
C2—C1—H1	119.4	N10—C14—C13	123.6 (2)
C11—C1—H1	119.4	C5—C14—C13	118.0 (2)
C1—C2—C3	120.2 (2)	O17—C15—O16	123.36 (19)
C1—C2—H2	119.9	O17—C15—C9	125.1 (2)
C3—C2—H2	119.9	O16—C15—C9	111.52 (18)
C4—C3—C2	120.9 (2)	C15—O16—C18	116.42 (16)
C4—C3—H3	119.5	C23—C18—C19	124.5 (2)
C2—C3—H3	119.5	C23—C18—O16	116.07 (19)
C3—C4—C12	120.8 (2)	C19—C18—O16	119.39 (19)
C3—C4—H4	119.6	C18—C19—C20	116.1 (2)
C12—C4—H4	119.6	C18—C19—C24	122.3 (2)
C6—C5—C14	121.3 (2)	C20—C19—C24	121.6 (2)
C6—C5—H5	119.3	C21—C20—C19	121.5 (2)
C14—C5—H5	119.3	C21—C20—H20	119.3
C5—C6—C7	120.6 (2)	C19—C20—H20	119.3
C5—C6—H6	119.7	C20—C21—C22	120.4 (2)
C7—C6—H6	119.7	C20—C21—H21A	119.8
C8—C7—C6	120.6 (2)	C22—C21—H21A	119.8
C8—C7—H7	119.7	C21—C22—C23	121.1 (2)
C6—C7—H7	119.7	C21—C22—H22	119.5
C7—C8—C13	121.0 (2)	C23—C22—H22	119.5
C7—C8—H8	119.5	C18—C23—C22	116.5 (2)
C13—C8—H8	119.5	C18—C23—C25	122.1 (2)
C11—C9—C13	120.48 (19)	C22—C23—C25	121.4 (2)
C11—C9—C15	118.01 (19)	C19—C24—H24A	109.5
C13—C9—C15	121.49 (19)	C19—C24—H24B	109.5
C14—N10—C12	118.28 (18)	H24A—C24—H24B	109.5
C9—C11—C1	124.1 (2)	C19—C24—H24C	109.5
C9—C11—C12	117.5 (2)	H24A—C24—H24C	109.5
C1—C11—C12	118.37 (19)	H24B—C24—H24C	109.5
N10—C12—C4	118.4 (2)	C23—C25—H25A	109.5
N10—C12—C11	123.1 (2)	C23—C25—H25B	109.5
C4—C12—C11	118.5 (2)	H25A—C25—H25B	109.5
C9—C13—C8	124.7 (2)	C23—C25—H25C	109.5
C9—C13—C14	116.9 (2)	H25A—C25—H25C	109.5
C8—C13—C14	118.4 (2)	H25B—C25—H25C	109.5
C11—C1—C2—C3	−0.2 (3)	C6—C5—C14—N10	−178.5 (2)
C1—C2—C3—C4	−0.5 (3)	C6—C5—C14—C13	0.4 (3)
C2—C3—C4—C12	0.3 (3)	C9—C13—C14—N10	−2.0 (3)
C14—C5—C6—C7	0.0 (4)	C8—C13—C14—N10	178.56 (19)
C5—C6—C7—C8	−0.6 (4)	C9—C13—C14—C5	179.15 (18)
C6—C7—C8—C13	0.7 (4)	C8—C13—C14—C5	−0.3 (3)
C13—C9—C11—C1	179.93 (19)	C11—C9—C15—O17	−65.5 (3)
C15—C9—C11—C1	1.3 (3)	C13—C9—C15—O17	115.9 (2)
C13—C9—C11—C12	2.3 (3)	C11—C9—C15—O16	111.8 (2)
C15—C9—C11—C12	−176.36 (18)	C13—C9—C15—O16	−66.8 (2)
C2—C1—C11—C9	−176.7 (2)	O17—C15—O16—C18	12.0 (3)
C2—C1—C11—C12	1.0 (3)	C9—C15—O16—C18	−165.32 (17)
C14—N10—C12—C4	−178.49 (18)	C15—O16—C18—C23	100.9 (2)
C14—N10—C12—C11	1.1 (3)	C15—O16—C18—C19	−82.0 (2)
C3—C4—C12—N10	−179.8 (2)	C23—C18—C19—C20	−2.0 (3)
C3—C4—C12—C11	0.6 (3)	O16—C18—C19—C20	−178.9 (2)
C9—C11—C12—N10	−2.9 (3)	C23—C18—C19—C24	177.0 (2)
C1—C11—C12—N10	179.25 (18)	O16—C18—C19—C24	0.1 (3)
C9—C11—C12—C4	176.66 (18)	C18—C19—C20—C21	0.1 (4)
C1—C11—C12—C4	−1.2 (3)	C24—C19—C20—C21	−178.9 (3)
C11—C9—C13—C8	179.43 (19)	C19—C20—C21—C22	1.4 (4)
C15—C9—C13—C8	−2.0 (3)	C20—C21—C22—C23	−1.1 (4)
C11—C9—C13—C14	0.0 (3)	C19—C18—C23—C22	2.3 (3)
C15—C9—C13—C14	178.56 (18)	O16—C18—C23—C22	179.24 (19)
C7—C8—C13—C9	−179.7 (2)	C19—C18—C23—C25	−177.5 (2)
C7—C8—C13—C14	−0.2 (3)	O16—C18—C23—C25	−0.6 (3)
C12—N10—C14—C5	−179.71 (18)	C21—C22—C23—C18	−0.7 (4)
C12—N10—C14—C13	1.4 (3)	C21—C22—C23—C25	179.2 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	1i	4.040 (2)	0.0 (2)	3.396 (1)	2.188 (2)
1	1ii	4.101 (2)	0.0 (2)	3.375 (1)	2.330 (2)
1	2i	3.632 (2)	2.0 (2)	3.348 (1)	1.408 (2)
1	3ii	3.914 (2)	1.1 (2)	3.338 (1)	2.044 (2)
2	1i	3.632 (2)	2.0 (2)	3.373 (1)	1.347 (2)
2	3i	3.990 (2)	3.0 (2)	3.400 (1)	2.088 (2)
2	3ii	4.071 (2)	3.0 (2)	3.365 (1)	2.291 (2)
3	1ii	3.914 (2)	1.1 (2)	3.371 (1)	1.989 (2)
3	2i	3.990 (2)	3.0 (2)	3.306 (1)	2.234 (2)
3	2ii	4.071 (2)	3.0 (2)	3.413 (1)	2.219 (2)