2,6-Dimethyl­phenyl acridine-9-carboxyl­ate

Trzybiński, D.; Wera, M.; Krzymiński, K.; Błażejowski, J.

doi:10.1107/S160053681205129X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o166

doi:10.1107/S160053681205129X

Open

access

2,6-Dimethylphenyl acridine-9-carboxylate

Damian Trzybiński,^a Michał Wera,^a Karol Krzymiński ^a and Jerzy Błażejowski ^a ^*

^aFaculty of Chemistry, University of Gdańsk, J. Sobieskiego 18, 80-952 Gdańsk, Poland
^*Correspondence e-mail: bla@chem.univ.gda.pl

(Received 18 December 2012; accepted 19 December 2012; online 4 January 2013)

In the title compound, C₂₂H₁₇NO₂, 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, molecules are arranged in stacks along the b axis, with all of the acridine rings involved in multiple π–π interactions [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_r = 327.37
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) 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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.151
S = 0.97
2913 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681205129X/ng5313sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681205129X/ng5313Isup3.cml

checkCIF report

Comment top

Phenyl acridine-9-carboxylates are the precursors of 9-(phenoxycarbonyl)-10-methylacridinium salts, whose cations exhibit a chemiluminogenic ability that can be utilized analytically (Natrajan et al., 2012). Here we present the structure of the precursor of one of the chemiluminogens that we have recently investigated (Krzymiński et al., 2011).

The bond lengths and angles characterizing the geometry of the acridine and phenyl moieties of the title compound (Fig. 1) are similar to those found in earlier investigated phenyl acridine-9-carboxylates alkyl-substituted at the benzene ring (Sikorski et al., 2005; Sikorski et al., 2006). With respective average deviations from planarity of 0.0245 (3) Å and 0.0084 (3) Å, the acridine and benzene ring systems are oriented at a dihedral angle of 37.7 (1)° (this angle is equal to 30.0 (2)° in 2-methylphenyl acridine-9-carboxylate (Sikorski et al., 2006) and 35.7 (2)° in 2,5-dimethylphenyl acridine-9-carboxylate (Sikorski et al., 2005)). The carboxyl group is twisted at an angle of 67.7 (1)° relative to the acridine skeleton (this angle is equal to 58.0 (2)° in 2-methylphenyl acridine-9-carboxylate (Sikorski et al., 2006) and 68.1 (2)° in 2,5-dimethylphenyl acridine-9-carboxylate (Sikorski et al., 2005)).

The search for intermolecular interactions in the crystal using PLATON (Spek, 2009) has shown that the inversely related molecules of the title compound (Fig. 2) are arranged in stacks along the b axis (Fig. 3) in which all acridine rings are involved in multiple π–π interactions (Table 1, Fig. 2) of an attractive nature (Hunter et al., 2001). The acridine moieties are parallel in stacks but inclined at an angle of 52.7 (1)° in adjacent stacks. The crystal structure is stabilized by dispersive interactions between neighboring stacks. This interesting crystal architecture is unique among the structures of phenyl acridine-9-carboxylates determined to date.

Related literature top

For a 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 top

2,6-Dimethylphenyl acridine-9-carboxylate was synthesized by the esterification of 9-(chlorocarbonyl)acridine (obtained in the reaction of acridine-9-carboxylic acid with a tenfold molar excess of thionyl chloride) with 2,6-dimethylphenol in anhydrous dichloromethane in the presence of N,N-diethylethanamine and a catalytic amount of N,N-dimethyl-4-pyridinamine (308–313 K, 25 h) (Sato, 1996; Sikorski et al., 2005). The product was purified chromatographically (SiO₂, cyclohexane/ethyl acetate, 1/1 v/v). Light-yellow crystals suitable for X-ray investigations were grown from cyclohexane (m.p. 434.5–435.5 K).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 25% probability level and H atoms are shown as small spheres of arbitrary radius. Cg1, Cg2 and Cg3 denote the ring centroids.
	Fig. 2. The arrangement of the molecules in the crystal structure. The π–π contacts are represented by dotted lines. H atoms have been omitted. [Symmetry codes: (i) –x + 1, –y + 2, –z; (ii) –x + 1, –y + 1, –z.]
	Fig. 3. Molecular stacks in the crystal structure, viewed along the b axis. H atoms have been omitted.

2,6-Dimethylphenyl acridine-9-carboxylate top

Crystal data top

C₂₂H₁₇NO₂	F(000) = 688
M_r = 327.37	D_x = 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

Data collection top

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	R_int = 0.064
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −15→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→8
T_min = 0.349, T_max = 1.000	l = −18→20
10387 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0773P)²] where P = (F_o² + 2F_c²)/3
2913 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₁₇NO₂	V = 1660.6 (2) Å³
M_r = 327.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8617 (10) Å	µ = 0.08 mm⁻¹
b = 7.5352 (5) Å	T = 295 K
c = 17.5950 (15) Å	0.45 × 0.12 × 0.05 mm
β = 103.143 (8)°

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2913 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	1908 reflections with I > 2σ(I)
T_min = 0.349, T_max = 1.000	R_int = 0.064
10387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 0.97	Δρ_max = 0.18 e Å⁻³
2913 reflections	Δρ_min = −0.24 e Å⁻³
228 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇NO₂
M_r	327.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.8617 (10), 7.5352 (5), 17.5950 (15)
β (°)	103.143 (8)
V (Å³)	1660.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.12 × 0.05

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.349, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10387, 2913, 1908
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.151, 0.97
No. of reflections	2913
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

π–π interactions (Å, °). top

Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 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	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)

Symmetry codes: (i) –x + 1, –y + 2, –z; (ii) –x + 1, –y + 1, –z.

Acknowledgements

This study was financed by the State Funds for Scientific Research through National Center for Science grant No. N N204 375 740 (contract No. 3757/B/H03/2011/40).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hunter, C. A., Lawson, K. R., Perkins, J. & Urch, C. J. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 651–669. Web of Science CrossRef Google Scholar
Krzymiński, K., Ożóg, A., Malecha, P., Roshal, A. D., Wróblewska, A., Zadykowicz, B. & Błażejowski, J. (2011). J. Org. Chem. 76, 1072–1085. Web of Science PubMed Google Scholar
Natrajan, A., Sharpe, D. & Wen, D. (2012). Org. Biomol. Chem. 10, 3432–3447. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sato, N. (1996). Tetrahedron Lett. 37, 8519–8522. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sikorski, A., Krzymiński, K., Białońska, A., Lis, T. & Błażejowski, J. (2006). Acta Cryst. E62, o555–o558. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sikorski, A., Krzymiński, K., Konitz, A. & Błażejowski, J. (2005). Acta Cryst. C61, o50–o52. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar