9-[Ethoxy­(8-quinolyl­amino)­methyl]­anthracene

The title compound, C₂₆H₂₂N₂O, was readily synthesized from the reaction between 8-amino­quinoline and 9-anthr­aldehyde in EtOH solution. There is an intramolecular N—H...N hydrogen bond and weak C—H...N/O interactions. The mol­ecule self-assembles into a zigzag chain along the c axis through π–π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.152
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

9-[Ethoxy(quinolin-8-ylamino)methyl]anthracene

Crystal data

C26H22N2O	F(000) = 800
Mr = 378.46	Dx = 1.285 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3698 reflections
a = 9.268 (2) Å	θ = 2.6–26.1°
b = 14.595 (2) Å	µ = 0.08 mm^−1
c = 14.466 (2) Å	T = 293 K
β = 90.09 (1)°	Hexagonal, yellow
V = 1956.8 (6) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3873 independent reflections
Radiation source: sealed tube	2684 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan [SADABS (Sheldrick, 1996) in SAINT (Bruker, 2000)]	h = −10→11
Tmin = 0.979, Tmax = 0.982	k = −18→18
10778 measured reflections	l = −17→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0885P)^2] where P = (Fo^2 + 2Fc^2)/3
3873 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.1496 (2)	0.65228 (13)	0.98793 (13)	0.0602 (5)
H1	−0.217 (2)	0.6726 (12)	0.9495 (13)	0.069 (6)*
C2	−0.1986 (2)	0.63714 (13)	1.07405 (13)	0.0695 (5)
H2	−0.2960	0.6455	1.0870	0.083*
C3	−0.1044 (3)	0.60877 (14)	1.14482 (13)	0.0719 (6)
H3	−0.1394	0.5980	1.2040	0.086*
C4	0.0358 (2)	0.59735 (13)	1.12640 (12)	0.0662 (5)
H4	0.0973	0.5784	1.1735	0.079*
C5	0.2375 (2)	0.60313 (11)	1.01931 (12)	0.0607 (5)
H5	0.2976	0.5831	1.0667	0.073*
C6	0.4472 (2)	0.61175 (13)	0.91663 (15)	0.0690 (5)
H6	0.5076	0.5921	0.9640	0.083*
C7	0.5035 (2)	0.63022 (14)	0.83394 (16)	0.0735 (6)
H7	0.6019	0.6228	0.8241	0.088*
C8	0.4145 (2)	0.66081 (13)	0.76169 (14)	0.0702 (5)
H8	0.4551	0.6747	0.7047	0.084*
C9	0.2708 (2)	0.67035 (12)	0.77368 (12)	0.0588 (5)
H9	0.2141	0.6906	0.7247	0.071*
C10	0.05491 (18)	0.65708 (10)	0.87576 (10)	0.0460 (4)
C11	−0.00253 (18)	0.64118 (10)	0.96416 (11)	0.0476 (4)
C12	0.0934 (2)	0.61331 (11)	1.03704 (11)	0.0532 (4)
C13	0.29706 (19)	0.62142 (11)	0.93397 (12)	0.0551 (4)
C14	0.20433 (18)	0.64997 (10)	0.86002 (11)	0.0497 (4)
C15	−0.04324 (19)	0.67899 (11)	0.79479 (11)	0.0478 (4)
H15	−0.1427 (18)	0.6887 (11)	0.8090 (11)	0.053 (5)*
C16	−0.13205 (17)	0.59360 (10)	0.65871 (10)	0.0466 (4)
C17	−0.23372 (18)	0.65596 (12)	0.63211 (11)	0.0547 (4)
H17	−0.2409	0.7118	0.6627	0.066*
C18	−0.3275 (2)	0.63583 (13)	0.55846 (12)	0.0649 (5)
H18	−0.3965	0.6788	0.5411	0.078*
C19	−0.3198 (2)	0.55557 (14)	0.51241 (12)	0.0659 (5)
H19	−0.3835	0.5437	0.4642	0.079*
C20	−0.1972 (2)	0.40568 (13)	0.49138 (12)	0.0672 (5)
H20	−0.2569	0.3902	0.4421	0.081*
C21	−0.0927 (2)	0.34720 (13)	0.51907 (13)	0.0684 (6)
H21	−0.0788	0.2918	0.4887	0.082*
C22	−0.0066 (2)	0.37139 (12)	0.59362 (12)	0.0625 (5)
H22	0.0641	0.3302	0.6126	0.075*
C23	−0.12182 (17)	0.50827 (10)	0.61103 (10)	0.0461 (4)
C24	−0.21585 (18)	0.48981 (12)	0.53700 (11)	0.0549 (4)
C25	−0.0162 (3)	0.92527 (15)	0.76706 (15)	0.0953 (8)
H25A	0.0872	0.9294	0.7663	0.143*
H25B	−0.0550	0.9749	0.8027	0.143*
H25C	−0.0524	0.9287	0.7049	0.143*
C26	−0.0588 (3)	0.83952 (13)	0.80780 (14)	0.0797 (6)
H26A	−0.0185	0.8347	0.8695	0.096*
H26B	−0.1631	0.8373	0.8128	0.096*
N1	−0.03296 (16)	0.60819 (10)	0.72798 (9)	0.0559 (4)
H1A	0.0210 (17)	0.5591 (12)	0.7405 (11)	0.056 (5)*
N2	−0.01852 (15)	0.44871 (9)	0.63903 (9)	0.0533 (4)
O1	−0.00976 (12)	0.76447 (7)	0.75287 (7)	0.0571 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0643 (12)	0.0675 (12)	0.0487 (10)	0.0040 (9)	−0.0101 (9)	0.0021 (9)
C2	0.0732 (13)	0.0811 (13)	0.0542 (11)	0.0048 (10)	0.0041 (9)	0.0017 (10)
C3	0.0991 (17)	0.0720 (13)	0.0448 (10)	0.0024 (11)	−0.0003 (10)	0.0073 (9)
C4	0.0868 (15)	0.0651 (12)	0.0467 (10)	0.0021 (10)	−0.0134 (9)	0.0081 (8)
C5	0.0710 (13)	0.0558 (10)	0.0553 (11)	0.0030 (9)	−0.0246 (9)	0.0035 (8)
C6	0.0611 (12)	0.0643 (12)	0.0816 (14)	0.0003 (9)	−0.0210 (10)	−0.0072 (10)
C7	0.0531 (11)	0.0783 (13)	0.0890 (16)	−0.0050 (10)	−0.0032 (11)	−0.0187 (12)
C8	0.0650 (13)	0.0773 (13)	0.0684 (13)	−0.0081 (10)	0.0055 (10)	−0.0127 (10)
C9	0.0621 (11)	0.0615 (10)	0.0529 (11)	−0.0054 (9)	−0.0061 (8)	−0.0076 (8)
C10	0.0557 (10)	0.0398 (8)	0.0425 (9)	−0.0026 (7)	−0.0109 (7)	−0.0038 (7)
C11	0.0597 (10)	0.0398 (8)	0.0433 (9)	−0.0017 (7)	−0.0113 (7)	−0.0030 (7)
C12	0.0705 (12)	0.0434 (9)	0.0456 (9)	0.0001 (8)	−0.0135 (8)	0.0019 (7)
C13	0.0593 (11)	0.0459 (9)	0.0601 (11)	−0.0006 (8)	−0.0163 (8)	−0.0059 (8)
C14	0.0608 (11)	0.0407 (8)	0.0474 (9)	−0.0031 (7)	−0.0106 (8)	−0.0070 (7)
C15	0.0563 (11)	0.0465 (9)	0.0407 (9)	0.0019 (8)	−0.0085 (7)	−0.0023 (7)
C16	0.0552 (10)	0.0490 (9)	0.0355 (8)	−0.0069 (7)	−0.0049 (7)	0.0020 (7)
C17	0.0617 (11)	0.0562 (10)	0.0462 (9)	0.0043 (8)	−0.0083 (8)	−0.0018 (8)
C18	0.0619 (11)	0.0752 (12)	0.0576 (11)	0.0038 (9)	−0.0170 (9)	0.0065 (10)
C19	0.0668 (12)	0.0809 (13)	0.0498 (10)	−0.0112 (10)	−0.0217 (8)	0.0009 (9)
C20	0.0885 (14)	0.0683 (12)	0.0448 (10)	−0.0272 (11)	−0.0043 (9)	−0.0079 (9)
C21	0.0999 (16)	0.0491 (10)	0.0562 (11)	−0.0174 (10)	0.0101 (11)	−0.0082 (9)
C22	0.0856 (14)	0.0445 (9)	0.0574 (11)	−0.0058 (9)	0.0054 (10)	0.0039 (8)
C23	0.0584 (10)	0.0460 (8)	0.0339 (8)	−0.0103 (7)	−0.0016 (7)	0.0053 (7)
C24	0.0695 (11)	0.0584 (10)	0.0368 (8)	−0.0184 (9)	−0.0035 (8)	0.0017 (7)
C25	0.149 (2)	0.0628 (13)	0.0739 (15)	0.0005 (14)	−0.0025 (14)	0.0010 (11)
C26	0.1232 (19)	0.0555 (11)	0.0604 (12)	0.0016 (11)	0.0042 (12)	−0.0068 (9)
N1	0.0693 (10)	0.0482 (8)	0.0500 (8)	0.0079 (7)	−0.0215 (7)	−0.0091 (6)
N2	0.0708 (9)	0.0437 (7)	0.0455 (8)	−0.0035 (6)	−0.0042 (6)	0.0034 (6)
O1	0.0786 (8)	0.0471 (6)	0.0458 (6)	0.0012 (6)	−0.0055 (6)	0.0001 (5)

Geometric parameters (Å, º)

C1—C2	1.345 (3)	C15—H15	0.955 (17)
C1—C11	1.416 (3)	C16—C17	1.365 (2)
C1—H1	0.885 (18)	C16—N1	1.3748 (19)
C2—C3	1.407 (3)	C16—C23	1.427 (2)
C2—H2	0.9300	C17—C18	1.405 (2)
C3—C4	1.337 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.350 (3)
C4—C12	1.419 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C24	1.405 (2)
C5—C12	1.368 (3)	C19—H19	0.9300
C5—C13	1.379 (3)	C20—C21	1.351 (3)
C5—H5	0.9300	C20—C24	1.405 (2)
C6—C7	1.333 (3)	C20—H20	0.9300
C6—C13	1.422 (3)	C21—C22	1.386 (3)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.403 (3)	C22—N2	1.311 (2)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.351 (3)	C23—N2	1.3546 (19)
C8—H8	0.9300	C23—C24	1.406 (2)
C9—C14	1.425 (2)	C25—C26	1.439 (3)
C9—H9	0.9300	C25—H25A	0.9600
C10—C11	1.405 (2)	C25—H25B	0.9600
C10—C14	1.408 (2)	C25—H25C	0.9600
C10—C15	1.516 (2)	C26—O1	1.428 (2)
C11—C12	1.437 (2)	C26—H26A	0.9700
C13—C14	1.433 (2)	C26—H26B	0.9700
C15—N1	1.418 (2)	N1—H1A	0.892 (17)
C15—O1	1.4217 (19)
C2—C1—C11	122.18 (17)	O1—C15—H15	99.9 (9)
C2—C1—H1	113.5 (13)	C10—C15—H15	116.3 (10)
C11—C1—H1	124.2 (13)	C17—C16—N1	124.20 (15)
C1—C2—C3	120.8 (2)	C17—C16—C23	119.48 (14)
C1—C2—H2	119.6	N1—C16—C23	116.28 (14)
C3—C2—H2	119.6	C16—C17—C18	120.02 (16)
C4—C3—C2	119.59 (19)	C16—C17—H17	120.0
C4—C3—H3	120.2	C18—C17—H17	120.0
C2—C3—H3	120.2	C19—C18—C17	121.49 (17)
C3—C4—C12	121.88 (17)	C19—C18—H18	119.3
C3—C4—H4	119.1	C17—C18—H18	119.3
C12—C4—H4	119.1	C18—C19—C24	120.33 (16)
C12—C5—C13	122.62 (16)	C18—C19—H19	119.8
C12—C5—H5	118.7	C24—C19—H19	119.8
C13—C5—H5	118.7	C21—C20—C24	120.11 (16)
C7—C6—C13	121.50 (18)	C21—C20—H20	119.9
C7—C6—H6	119.2	C24—C20—H20	119.9
C13—C6—H6	119.2	C20—C21—C22	118.76 (17)
C6—C7—C8	120.17 (19)	C20—C21—H21	120.6
C6—C7—H7	119.9	C22—C21—H21	120.6
C8—C7—H7	119.9	N2—C22—C21	124.08 (18)
C9—C8—C7	121.0 (2)	N2—C22—H22	118.0
C9—C8—H8	119.5	C21—C22—H22	118.0
C7—C8—H8	119.5	N2—C23—C24	122.81 (15)
C8—C9—C14	121.25 (18)	N2—C23—C16	117.58 (13)
C8—C9—H9	119.4	C24—C23—C16	119.60 (15)
C14—C9—H9	119.4	C20—C24—C19	124.26 (16)
C11—C10—C14	120.61 (14)	C20—C24—C23	116.66 (17)
C11—C10—C15	120.68 (15)	C19—C24—C23	119.07 (16)
C14—C10—C15	118.68 (15)	C26—C25—H25A	109.5
C10—C11—C1	124.64 (14)	C26—C25—H25B	109.5
C10—C11—C12	118.66 (16)	H25A—C25—H25B	109.5
C1—C11—C12	116.69 (16)	C26—C25—H25C	109.5
C5—C12—C4	121.45 (16)	H25A—C25—H25C	109.5
C5—C12—C11	119.74 (16)	H25B—C25—H25C	109.5
C4—C12—C11	118.81 (17)	O1—C26—C25	110.56 (18)
C5—C13—C6	122.16 (17)	O1—C26—H26A	109.5
C5—C13—C14	118.94 (17)	C25—C26—H26A	109.5
C6—C13—C14	118.90 (18)	O1—C26—H26B	109.5
C10—C14—C9	123.58 (15)	C25—C26—H26B	109.5
C10—C14—C13	119.32 (16)	H26A—C26—H26B	108.1
C9—C14—C13	117.10 (16)	C16—N1—C15	124.35 (14)
N1—C15—O1	109.50 (13)	C16—N1—H1A	113.4 (10)
N1—C15—C10	109.39 (13)	C15—N1—H1A	119.0 (10)
O1—C15—C10	112.56 (13)	C22—N2—C23	117.57 (14)
N1—C15—H15	108.7 (10)	C15—O1—C26	111.46 (14)
C11—C1—C2—C3	−0.4 (3)	C6—C13—C14—C9	−2.3 (2)
C1—C2—C3—C4	0.6 (3)	C11—C10—C15—N1	−116.18 (16)
C2—C3—C4—C12	0.1 (3)	C14—C10—C15—N1	61.75 (18)
C13—C6—C7—C8	0.5 (3)	C11—C10—C15—O1	122.08 (16)
C6—C7—C8—C9	−1.3 (3)	C14—C10—C15—O1	−59.99 (18)
C7—C8—C9—C14	0.2 (3)	N1—C16—C17—C18	177.99 (16)
C14—C10—C11—C1	175.84 (14)	C23—C16—C17—C18	0.1 (2)
C15—C10—C11—C1	−6.3 (2)	C16—C17—C18—C19	−0.1 (3)
C14—C10—C11—C12	−2.9 (2)	C17—C18—C19—C24	−0.4 (3)
C15—C10—C11—C12	174.99 (13)	C24—C20—C21—C22	0.8 (3)
C2—C1—C11—C10	−179.17 (16)	C20—C21—C22—N2	−0.9 (3)
C2—C1—C11—C12	−0.4 (3)	C17—C16—C23—N2	179.43 (14)
C13—C5—C12—C4	−177.62 (15)	N1—C16—C23—N2	1.4 (2)
C13—C5—C12—C11	2.1 (2)	C17—C16—C23—C24	0.5 (2)
C3—C4—C12—C5	178.78 (17)	N1—C16—C23—C24	−177.58 (14)
C3—C4—C12—C11	−1.0 (3)	C18—C19—C24—C23	1.0 (3)
C10—C11—C12—C5	0.2 (2)	C18—C19—C24—C20	−178.11 (17)
C1—C11—C12—C5	−178.68 (15)	N2—C23—C24—C19	−179.88 (15)
C10—C11—C12—C4	179.92 (14)	C16—C23—C24—C19	−1.0 (2)
C1—C11—C12—C4	1.1 (2)	N2—C23—C24—C20	−0.7 (2)
C12—C5—C13—C6	179.16 (15)	C16—C23—C24—C20	178.14 (14)
C12—C5—C13—C14	−1.6 (2)	C21—C20—C24—C19	179.00 (17)
C7—C6—C13—C5	−179.49 (17)	C21—C20—C24—C23	−0.1 (2)
C7—C6—C13—C14	1.3 (3)	C17—C16—N1—C15	15.5 (3)
C11—C10—C14—C9	−176.17 (14)	C23—C16—N1—C15	−166.49 (15)
C15—C10—C14—C9	5.9 (2)	O1—C15—N1—C16	−73.8 (2)
C11—C10—C14—C13	3.4 (2)	C10—C15—N1—C16	162.47 (15)
C15—C10—C14—C13	−174.54 (13)	C21—C22—N2—C23	0.0 (3)
C8—C9—C14—C10	−178.80 (15)	C24—C23—N2—C22	0.8 (2)
C8—C9—C14—C13	1.6 (2)	C16—C23—N2—C22	−178.14 (14)
C5—C13—C14—C10	−1.1 (2)	N1—C15—O1—C26	162.75 (16)
C6—C13—C14—C10	178.09 (14)	C10—C15—O1—C26	−75.41 (18)
C5—C13—C14—C9	178.45 (15)	C25—C26—O1—C15	176.62 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.89 (2)	2.203 (17)	2.663 (2)	112 (1)
C9—H9···O1	0.93	2.38	2.956 (2)	120
C9—H9···N1	0.93	2.59	3.030 (2)	110