1-[9-Ethyl-6-(2-methyl­benzo­yl)-9H-carbazol-3-yl]ethanone

Hang, Y.-C.; Ji, J.-X.; Chen, M.-D.

doi:10.1107/S1600536809016080

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1198

doi:10.1107/S1600536809016080

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1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone

Ye-Chao Hang,^a ^* Jin-Xiu Ji ^b and Min-Dong Chen ^a

^aCollege of Environmental Science and Engineering, Nanjing University of Information Science and Technology, Nanjing 210044, People's Republic of China, and ^bResearch & Development Center, Sinochem Jiangsu Corporation, Nanjing 210005, People's Republic of China
^*Correspondence e-mail: hangyechao@yahoo.com.cn

(Received 2 April 2009; accepted 29 April 2009; online 7 May 2009)

In the title compound, C₂₄H₂₁NO₂, the pendant benzene ring is inclined at a dihedral angle of 86.66 (18)° with respect to the adjacent aromatic ring of the carbozole unit. In the crystal structure, symmetry-related molecules are linked via C—H⋯O and C—H⋯π interactions.

Related literature

For carbazole-containing compounds used as organic opto-electronic materials, see: Bai et al. (2007 ); Liu et al. (2009 ); Promarak et al. (2007 ). For the synthesis, see: Feng et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₁NO₂
M_r = 355.42
Orthorhombic, P b c a
a = 13.066 (3) Å
b = 13.416 (3) Å
c = 21.987 (4) Å
V = 3854.2 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.977, T_max = 0.992
3492 measured reflections
3492 independent reflections
1733 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.178
S = 1.06
3492 reflections
244 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1ⁱ	0.93	2.57	3.447 (5)	157
C16—H16A⋯O1ⁱ	0.97	2.54	3.476 (5)	163
C3—H3A⋯CgBⁱⁱ	0.93	2.78	3.671 (5)	161
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ . CgB is the centroid of the C9–C14 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016080/su2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016080/su2106Isup2.hkl

checkCIF report

Comment top

The title compound is an important intermediate in the synthesis of carbazole-containing compounds used as organic optoelectronic materials, which have large π—π conjugated networks (Bai et al. 2007; Promarak et al. 2007; Liu et al. 2009). Our interest in this field of research lead us to synthesize, and to report here on the crystal structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. The geometrical parameters are within normal ranges (Allen et al., 1987). The carbozole moiety is slighty bowed with ring B (C9—C14) being inclined to ring D (C17—C22) by 3.04 (19)°. The central ring C (N1,C12,C13,C17,C22) is inclined to rings B and D by 2.76 (18) and 0.30 (18)°, respectively. Ring A (C2—C7) is inclined to ring B by 86.66 (18)°.

In the crystal structure symmetry related molecules are linked via C—H···O and C—H···π interactions (Table 1 and Fig. 2).

Related literature top

For carbazole-containing compounds used as organic opto-electronic materials, see: Bai et al. (2007); Liu et al. (2009); Promarak et al. (2007). For the synthesis, see: Feng et al. (2007). For bond-length data, see: Allen et al. (1987). CgB is the centroid of the C9–C14 ring.

Experimental top

The title compound was prepared by a slight modification of a method reported in the literature (Feng et al., 2007). That is, the title compound was recrystalized from a mixture of methanol and dichloromethane (V/V = 2:1). On solw evaporation of the solvent colourless block-like crystals appeared after ca 4 days.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A view along the c axis of the crystal structure of the title compound.

1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone top

Crystal data top

C₂₄H₂₁NO₂	F(000) = 1504
M_r = 355.42	D_x = 1.225 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 13.066 (3) Å	θ = 9–13°
b = 13.416 (3) Å	µ = 0.08 mm⁻¹
c = 21.987 (4) Å	T = 298 K
V = 3854.2 (13) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1733 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 1.9°
ω/2θ scans	h = 0→15
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
T_min = 0.977, T_max = 0.992	l = 0→26
3492 measured reflections	3 standard reflections every 200 reflections
3492 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.07P)² + P] where P = (F_o² + 2F_c²)/3
3492 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.21 e Å⁻³
7 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₂₁NO₂	V = 3854.2 (13) Å³
M_r = 355.42	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.066 (3) Å	µ = 0.08 mm⁻¹
b = 13.416 (3) Å	T = 298 K
c = 21.987 (4) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1733 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.977, T_max = 0.992	3 standard reflections every 200 reflections
3492 measured reflections	intensity decay: 1%
3492 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	7 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
3492 reflections	Δρ_min = −0.21 e Å⁻³
244 parameters

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
N1	0.0687 (2)	0.16753 (19)	0.42892 (12)	0.0504 (8)
O1	0.0131 (2)	−0.1722 (2)	0.23132 (11)	0.0875 (10)
O2	0.2544 (2)	−0.1349 (2)	0.61640 (11)	0.0756 (9)
C1	0.2478 (3)	−0.2480 (4)	0.2692 (2)	0.0959 (15)
H1A	0.2169	−0.1881	0.2539	0.144*
H1B	0.2712	−0.2879	0.2357	0.144*
H1C	0.3047	−0.2312	0.2948	0.144*
C2	0.1690 (3)	−0.3066 (3)	0.30595 (16)	0.0585 (10)
C3	0.1953 (3)	−0.3949 (3)	0.33371 (19)	0.0737 (12)
H3A	0.2614	−0.4197	0.3291	0.088*
C4	0.1260 (4)	−0.4469 (3)	0.3680 (2)	0.0791 (13)
H4A	0.1452	−0.5065	0.3862	0.095*
C5	0.0289 (4)	−0.4116 (3)	0.37538 (19)	0.0795 (13)
H5A	−0.0184	−0.4462	0.3989	0.095*
C6	0.0025 (3)	−0.3240 (3)	0.34747 (17)	0.0634 (11)
H6A	−0.0639	−0.3001	0.3518	0.076*
C7	0.0713 (3)	−0.2700 (2)	0.31316 (14)	0.0469 (9)
C8	0.0415 (3)	−0.1750 (3)	0.28459 (15)	0.0506 (9)
C9	0.0412 (2)	−0.0846 (2)	0.32201 (14)	0.0441 (8)
C10	0.0086 (3)	0.0068 (3)	0.29808 (14)	0.0530 (9)
H10A	−0.0153	0.0084	0.2582	0.064*
C11	0.0103 (3)	0.0925 (3)	0.33004 (15)	0.0525 (9)
H11A	−0.0160	0.1512	0.3138	0.063*
C12	0.0532 (2)	0.0903 (2)	0.38852 (14)	0.0435 (8)
C13	0.0851 (2)	−0.0001 (2)	0.41460 (13)	0.0398 (8)
C14	0.0809 (2)	−0.0866 (2)	0.38160 (13)	0.0418 (8)
H14A	0.1041	−0.1461	0.3983	0.050*
C15	−0.0522 (4)	0.3030 (3)	0.4458 (2)	0.1066 (17)
H15A	−0.0635	0.3724	0.4377	0.160*
H15B	−0.0506	0.2922	0.4890	0.160*
H15C	−0.1067	0.2645	0.4283	0.160*
C16	0.0474 (3)	0.2716 (3)	0.41870 (18)	0.0673 (11)
H16A	0.0460	0.2844	0.3753	0.081*
H16B	0.1020	0.3113	0.4362	0.081*
C17	0.1146 (3)	0.1274 (2)	0.48129 (15)	0.0462 (8)
C18	0.1455 (3)	0.1773 (3)	0.53372 (15)	0.0561 (10)
H18A	0.1379	0.2458	0.5382	0.067*
C19	0.1877 (3)	0.1190 (3)	0.57813 (16)	0.0545 (10)
H19A	0.2101	0.1499	0.6136	0.065*
C20	0.1989 (2)	0.0176 (3)	0.57334 (14)	0.0477 (9)
C21	0.1685 (2)	−0.0315 (2)	0.52034 (14)	0.0442 (8)
H21A	0.1769	−0.1000	0.5158	0.053*
C22	0.1251 (2)	0.0261 (2)	0.47458 (14)	0.0439 (8)
C23	0.2439 (3)	−0.0457 (3)	0.62258 (16)	0.0537 (9)
C24	0.2761 (3)	0.0048 (3)	0.68053 (16)	0.0792 (13)
H24A	0.3027	−0.0439	0.7083	0.119*
H24B	0.2181	0.0374	0.6985	0.119*
H24C	0.3281	0.0533	0.6718	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.062 (2)	0.0374 (16)	0.0517 (16)	0.0044 (14)	−0.0039 (15)	0.0025 (13)
O1	0.126 (3)	0.0832 (19)	0.0536 (16)	0.0019 (17)	−0.0341 (18)	−0.0082 (14)
O2	0.092 (2)	0.0652 (19)	0.0696 (17)	0.0159 (15)	−0.0320 (16)	−0.0102 (15)
C1	0.055 (3)	0.126 (4)	0.107 (3)	0.009 (3)	0.000 (3)	0.025 (3)
C2	0.057 (3)	0.061 (2)	0.058 (2)	−0.001 (2)	−0.007 (2)	0.0023 (19)
C3	0.063 (3)	0.075 (3)	0.083 (3)	−0.003 (2)	−0.014 (2)	0.008 (2)
C4	0.088 (4)	0.065 (3)	0.084 (3)	0.004 (3)	−0.021 (3)	0.014 (2)
C5	0.088 (4)	0.082 (3)	0.068 (3)	−0.010 (3)	0.000 (3)	0.017 (2)
C6	0.062 (3)	0.066 (3)	0.062 (2)	0.001 (2)	0.001 (2)	−0.005 (2)
C7	0.045 (2)	0.058 (2)	0.0376 (17)	−0.0050 (18)	−0.0094 (16)	−0.0059 (16)
C8	0.047 (2)	0.059 (2)	0.045 (2)	−0.0036 (17)	−0.0077 (17)	−0.0025 (17)
C9	0.040 (2)	0.052 (2)	0.0400 (18)	−0.0051 (16)	−0.0008 (15)	−0.0030 (16)
C10	0.054 (2)	0.067 (2)	0.0377 (17)	−0.0016 (19)	−0.0066 (17)	−0.0007 (18)
C11	0.050 (2)	0.059 (2)	0.048 (2)	0.0083 (18)	−0.0008 (18)	0.0093 (18)
C12	0.039 (2)	0.044 (2)	0.0478 (19)	−0.0004 (16)	−0.0017 (16)	−0.0002 (17)
C13	0.0384 (19)	0.0406 (19)	0.0406 (17)	−0.0100 (15)	−0.0022 (15)	−0.0006 (16)
C14	0.0318 (18)	0.051 (2)	0.0429 (18)	0.0050 (15)	−0.0041 (15)	0.0022 (16)
C15	0.109 (4)	0.082 (3)	0.129 (4)	0.016 (3)	−0.001 (4)	−0.001 (3)
C16	0.082 (3)	0.057 (2)	0.063 (2)	−0.008 (2)	−0.010 (2)	0.0046 (19)
C17	0.049 (2)	0.037 (2)	0.053 (2)	0.0033 (15)	0.0019 (18)	−0.0017 (16)
C18	0.067 (3)	0.045 (2)	0.055 (2)	0.0018 (18)	−0.003 (2)	−0.0111 (18)
C19	0.057 (3)	0.053 (2)	0.054 (2)	−0.0043 (18)	−0.006 (2)	−0.0172 (18)
C20	0.035 (2)	0.064 (3)	0.0443 (18)	0.0001 (17)	−0.0045 (16)	−0.0131 (17)
C21	0.043 (2)	0.0440 (19)	0.0459 (18)	0.0038 (16)	−0.0064 (16)	−0.0024 (15)
C22	0.037 (2)	0.052 (2)	0.0425 (18)	−0.0023 (16)	0.0001 (16)	−0.0041 (15)
C23	0.048 (2)	0.051 (2)	0.062 (2)	−0.0021 (18)	−0.0097 (19)	−0.0116 (18)
C24	0.084 (3)	0.095 (3)	0.059 (2)	0.006 (3)	−0.024 (2)	−0.019 (2)

Geometric parameters (Å, º) top

N1—C12	1.380 (4)	C11—H11A	0.9300
N1—C17	1.406 (4)	C12—C13	1.405 (4)
N1—C16	1.442 (4)	C13—C14	1.369 (4)
O1—C8	1.229 (4)	C13—C22	1.462 (4)
O2—C23	1.212 (4)	C14—H14A	0.9300
C1—C2	1.527 (5)	C15—C16	1.492 (6)
C1—H1A	0.9600	C15—H15A	0.9600
C1—H1B	0.9600	C15—H15B	0.9600
C1—H1C	0.9600	C15—H15C	0.9600
C2—C3	1.376 (5)	C16—H16A	0.9700
C2—C7	1.377 (5)	C16—H16B	0.9700
C3—C4	1.369 (5)	C17—C22	1.373 (4)
C3—H3A	0.9300	C17—C18	1.393 (4)
C4—C5	1.365 (6)	C18—C19	1.367 (5)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.370 (5)	C19—C20	1.373 (5)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.379 (5)	C20—C21	1.397 (4)
C6—H6A	0.9300	C20—C23	1.496 (5)
C7—C8	1.473 (5)	C21—C22	1.390 (4)
C8—C9	1.466 (4)	C21—H21A	0.9300
C9—C10	1.399 (4)	C23—C24	1.503 (5)
C9—C14	1.409 (4)	C24—H24A	0.9600
C10—C11	1.348 (5)	C24—H24B	0.9600
C10—H10A	0.9300	C24—H24C	0.9600
C11—C12	1.403 (4)

C12—N1—C17	107.6 (2)	C12—C13—C22	105.4 (3)
C12—N1—C16	126.8 (3)	C13—C14—C9	119.4 (3)
C17—N1—C16	125.5 (3)	C13—C14—H14A	120.3
C2—C1—H1A	109.5	C9—C14—H14A	120.3
C2—C1—H1B	109.5	C16—C15—H15A	109.5
H1A—C1—H1B	109.5	C16—C15—H15B	109.5
C2—C1—H1C	109.5	H15A—C15—H15B	109.5
H1A—C1—H1C	109.5	C16—C15—H15C	109.5
H1B—C1—H1C	109.5	H15A—C15—H15C	109.5
C3—C2—C7	119.2 (4)	H15B—C15—H15C	109.5
C3—C2—C1	120.6 (4)	N1—C16—C15	112.3 (3)
C7—C2—C1	120.1 (3)	N1—C16—H16A	109.1
C4—C3—C2	121.1 (4)	C15—C16—H16A	109.1
C4—C3—H3A	119.4	N1—C16—H16B	109.1
C2—C3—H3A	119.4	C15—C16—H16B	109.1
C5—C4—C3	120.3 (4)	H16A—C16—H16B	107.9
C5—C4—H4A	119.9	C22—C17—C18	122.4 (3)
C3—C4—H4A	119.9	C22—C17—N1	109.5 (3)
C4—C5—C6	118.6 (4)	C18—C17—N1	128.1 (3)
C4—C5—H5A	120.7	C19—C18—C17	115.7 (3)
C6—C5—H5A	120.7	C19—C18—H18A	122.1
C5—C6—C7	122.1 (4)	C17—C18—H18A	122.1
C5—C6—H6A	118.9	C18—C19—C20	123.7 (3)
C7—C6—H6A	118.9	C18—C19—H19A	118.1
C2—C7—C6	118.7 (3)	C20—C19—H19A	118.1
C2—C7—C8	120.3 (3)	C19—C20—C21	120.1 (3)
C6—C7—C8	121.0 (3)	C19—C20—C23	123.3 (3)
O1—C8—C9	120.6 (3)	C21—C20—C23	116.6 (3)
O1—C8—C7	120.8 (3)	C22—C21—C20	117.2 (3)
C9—C8—C7	118.5 (3)	C22—C21—H21A	121.4
C10—C9—C14	118.6 (3)	C20—C21—H21A	121.4
C10—C9—C8	121.0 (3)	C17—C22—C21	120.9 (3)
C14—C9—C8	120.3 (3)	C17—C22—C13	107.4 (3)
C11—C10—C9	123.1 (3)	C21—C22—C13	131.6 (3)
C11—C10—H10A	118.5	O2—C23—C20	121.6 (3)
C9—C10—H10A	118.5	O2—C23—C24	120.6 (4)
C10—C11—C12	117.8 (3)	C20—C23—C24	117.9 (3)
C10—C11—H11A	121.1	C23—C24—H24A	109.5
C12—C11—H11A	121.1	C23—C24—H24B	109.5
N1—C12—C11	129.3 (3)	H24A—C24—H24B	109.5
N1—C12—C13	110.0 (3)	C23—C24—H24C	109.5
C11—C12—C13	120.7 (3)	H24A—C24—H24C	109.5
C14—C13—C12	120.2 (3)	H24B—C24—H24C	109.5
C14—C13—C22	134.2 (3)

C7—C2—C3—C4	0.3 (6)	C12—C13—C14—C9	−2.1 (5)
C1—C2—C3—C4	178.5 (4)	C22—C13—C14—C9	−176.2 (3)
C2—C3—C4—C5	−0.2 (6)	C10—C9—C14—C13	1.1 (5)
C3—C4—C5—C6	0.6 (6)	C8—C9—C14—C13	176.4 (3)
C4—C5—C6—C7	−1.1 (6)	C12—N1—C16—C15	98.8 (4)
C3—C2—C7—C6	−0.8 (5)	C17—N1—C16—C15	−84.8 (4)
C1—C2—C7—C6	−178.9 (3)	C12—N1—C17—C22	−1.7 (4)
C3—C2—C7—C8	179.2 (3)	C16—N1—C17—C22	−178.6 (3)
C1—C2—C7—C8	1.1 (5)	C12—N1—C17—C18	179.1 (3)
C5—C6—C7—C2	1.2 (5)	C16—N1—C17—C18	2.1 (6)
C5—C6—C7—C8	−178.8 (3)	C22—C17—C18—C19	0.4 (5)
C2—C7—C8—O1	84.0 (4)	N1—C17—C18—C19	179.6 (3)
C6—C7—C8—O1	−95.9 (4)	C17—C18—C19—C20	−0.8 (5)
C2—C7—C8—C9	−99.3 (4)	C18—C19—C20—C21	1.4 (5)
C6—C7—C8—C9	80.8 (4)	C18—C19—C20—C23	−179.1 (3)
O1—C8—C9—C10	0.0 (5)	C19—C20—C21—C22	−1.5 (5)
C7—C8—C9—C10	−176.8 (3)	C23—C20—C21—C22	179.0 (3)
O1—C8—C9—C14	−175.3 (3)	C18—C17—C22—C21	−0.5 (5)
C7—C8—C9—C14	8.0 (5)	N1—C17—C22—C21	−179.9 (3)
C14—C9—C10—C11	−2.3 (5)	C18—C17—C22—C13	−180.0 (3)
C8—C9—C10—C11	−177.6 (3)	N1—C17—C22—C13	0.7 (4)
C9—C10—C11—C12	4.4 (5)	C20—C21—C22—C17	1.1 (5)
C17—N1—C12—C11	−179.7 (3)	C20—C21—C22—C13	−179.6 (3)
C16—N1—C12—C11	−2.8 (6)	C14—C13—C22—C17	175.3 (3)
C17—N1—C12—C13	2.0 (4)	C12—C13—C22—C17	0.5 (4)
C16—N1—C12—C13	178.9 (3)	C14—C13—C22—C21	−4.1 (6)
C10—C11—C12—N1	176.5 (3)	C12—C13—C22—C21	−178.8 (3)
C10—C11—C12—C13	−5.3 (5)	C19—C20—C23—O2	−178.7 (4)
N1—C12—C13—C14	−177.2 (3)	C21—C20—C23—O2	0.8 (5)
C11—C12—C13—C14	4.3 (5)	C19—C20—C23—C24	1.4 (5)
N1—C12—C13—C22	−1.6 (4)	C21—C20—C23—C24	−179.2 (3)
C11—C12—C13—C22	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.93	2.57	3.447 (5)	157
C16—H16A···O1ⁱ	0.97	2.54	3.476 (5)	163
C3—H3A···CgBⁱⁱ	0.93	2.78	3.671 (5)	161

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁NO₂
M_r	355.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.066 (3), 13.416 (3), 21.987 (4)
V (Å³)	3854.2 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	3492, 3492, 1733
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.178, 1.06
No. of reflections	3492
No. of parameters	244
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.93	2.57	3.447 (5)	157
C16—H16A···O1ⁱ	0.97	2.54	3.476 (5)	163
C3—H3A···CgBⁱⁱ	0.93	2.78	3.671 (5)	161

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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