Ethyl trans-12-(pyridin-4-yl)-9,10-ethano-anthracene-11-carboxyl-ate.

In the title compound, C24H21NO2, the residues at the central ethyl-ene bridge are trans to each other. The dihedral angles between the pyridine and benzene rings are 67.09 (6) and 61.41 (5)°. In the crystal, centrosymmetrically related mol-ecules are linked into dimers by pairs of C-H⋯O hydrogen bonds.

Related literature

For the biological activity of ester derivatives, see: Bi et al. (2012 ▶); Bartzatt et al. (2004 ▶); Anadu et al. (2006 ▶). For conformation studies, see: Nardelli (1983 ▶). For a related structure, see: Gnanamani & Ramanathan (2009 ▶).

Experimental

Crystal data

C24H21NO2

M = 355.42

Monoclinic,

a = 10.1733 (19) Å

b = 11.156 (2) Å

c = 16.361 (3) Å

β = 90.877 (3)°

V = 1856.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.40 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.969, T max = 0.984

18677 measured reflections

3664 independent reflections

3105 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.05

3664 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, 2R. DOI: 10.1107/S1600536814006588/bt6931sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006588/bt6931Isup2.hkl

CCDC reference: 993524

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H21NO2	F(000) = 752
Mr = 355.42	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9754 reflections
a = 10.1733 (19) Å	θ = 2.2–26.0°
b = 11.156 (2) Å	µ = 0.08 mm−1
c = 16.361 (3) Å	T = 298 K
β = 90.877 (3)°	Block, colourless
V = 1856.6 (6) Å3	0.40 × 0.38 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3664 independent reflections
Radiation source: fine-focus sealed tube	3105 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 15.9821 pixels mm-1	θmax = 26.1°, θmin = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.969, Tmax = 0.984	l = −20→20
18677 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.4341P] where P = (Fo2 + 2Fc2)/3
3664 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.59145 (13)	0.92171 (12)	0.85231 (8)	0.0392 (3)
C2	0.46282 (15)	0.90612 (15)	0.82600 (10)	0.0502 (4)
H2	0.4091	0.8500	0.8510	0.060*
C3	0.41498 (17)	0.97553 (18)	0.76167 (12)	0.0649 (5)
H3	0.3289	0.9652	0.7430	0.078*
C4	0.49392 (19)	1.05918 (18)	0.72543 (11)	0.0685 (5)
H4	0.4610	1.1050	0.6823	0.082*
C5	0.62142 (17)	1.07578 (16)	0.75239 (10)	0.0565 (4)
H5	0.6739	1.1334	0.7280	0.068*
C6	0.67128 (14)	1.00685 (13)	0.81564 (8)	0.0407 (3)
C7	0.80801 (13)	1.01204 (13)	0.85311 (9)	0.0406 (3)
H7	0.8639	1.0697	0.8248	0.049*
C8	0.79534 (12)	1.04310 (11)	0.94622 (8)	0.0354 (3)
H8	0.8826	1.0330	0.9715	0.042*
C9	0.70331 (12)	0.95000 (12)	0.98565 (8)	0.0341 (3)
H9	0.6244	0.9919	1.0039	0.041*
C10	0.66015 (13)	0.85398 (12)	0.92048 (8)	0.0381 (3)
H10	0.6035	0.7923	0.9440	0.046*
C11	0.78412 (14)	0.80130 (13)	0.88616 (9)	0.0425 (3)
C12	0.86419 (14)	0.88680 (14)	0.85040 (9)	0.0442 (3)
C13	0.98283 (16)	0.85354 (18)	0.81716 (11)	0.0623 (5)
H13	1.0384	0.9106	0.7947	0.075*
C14	1.0172 (2)	0.7333 (2)	0.81801 (14)	0.0812 (7)
H14	1.0962	0.7096	0.7951	0.097*
C15	0.9370 (2)	0.6489 (2)	0.85202 (14)	0.0788 (7)
H15	0.9615	0.5686	0.8511	0.095*
C16	0.82018 (18)	0.68175 (15)	0.88763 (11)	0.0582 (5)
H16	0.7669	0.6247	0.9121	0.070*
C17	0.75608 (13)	1.17233 (12)	0.95790 (8)	0.0381 (3)
C18	0.62967 (14)	1.21560 (13)	0.94575 (10)	0.0475 (4)
H18	0.5619	1.1633	0.9316	0.057*
C19	0.60451 (16)	1.33606 (14)	0.95456 (11)	0.0568 (4)
H19	0.5186	1.3623	0.9461	0.068*
C20	0.81530 (19)	1.37470 (16)	0.98575 (15)	0.0766 (6)
H20	0.8812	1.4293	0.9993	0.092*
C21	0.85033 (16)	1.25592 (14)	0.97912 (12)	0.0578 (4)
H21	0.9368	1.2323	0.9889	0.069*
C22	0.76667 (13)	0.88949 (12)	1.05943 (8)	0.0371 (3)
C23	0.73365 (16)	0.73634 (15)	1.15837 (9)	0.0513 (4)
H23A	0.6605	0.7091	1.1909	0.062*
H23B	0.7918	0.7833	1.1933	0.062*
C24	0.8059 (2)	0.63115 (16)	1.12588 (11)	0.0657 (5)
H24A	0.7502	0.5882	1.0881	0.099*
H24B	0.8310	0.5792	1.1702	0.099*
H24C	0.8831	0.6581	1.0983	0.099*
N1	0.69472 (15)	1.41714 (12)	0.97428 (11)	0.0713 (5)
O1	0.68494 (10)	0.81027 (9)	1.09130 (6)	0.0474 (3)
O2	0.87508 (11)	0.90811 (11)	1.08561 (7)	0.0628 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0418 (7)	0.0369 (7)	0.0388 (7)	0.0032 (6)	−0.0034 (6)	−0.0068 (6)
C2	0.0442 (8)	0.0539 (9)	0.0522 (9)	0.0000 (7)	−0.0074 (7)	−0.0095 (7)
C3	0.0498 (9)	0.0783 (13)	0.0659 (11)	0.0112 (9)	−0.0219 (8)	−0.0064 (10)
C4	0.0721 (12)	0.0729 (12)	0.0598 (11)	0.0150 (10)	−0.0192 (9)	0.0128 (9)
C5	0.0622 (10)	0.0562 (10)	0.0511 (9)	0.0068 (8)	−0.0028 (8)	0.0117 (8)
C6	0.0442 (8)	0.0404 (7)	0.0374 (7)	0.0065 (6)	−0.0001 (6)	−0.0016 (6)
C7	0.0388 (7)	0.0416 (8)	0.0416 (7)	0.0001 (6)	0.0052 (6)	0.0039 (6)
C8	0.0302 (6)	0.0331 (7)	0.0428 (7)	−0.0015 (5)	−0.0013 (5)	0.0013 (6)
C9	0.0318 (6)	0.0324 (7)	0.0381 (7)	−0.0005 (5)	−0.0001 (5)	−0.0011 (5)
C10	0.0406 (7)	0.0328 (7)	0.0408 (7)	−0.0045 (5)	−0.0042 (6)	−0.0010 (6)
C11	0.0484 (8)	0.0386 (8)	0.0403 (7)	0.0069 (6)	−0.0105 (6)	−0.0065 (6)
C12	0.0421 (8)	0.0510 (9)	0.0393 (7)	0.0092 (6)	−0.0030 (6)	−0.0072 (6)
C13	0.0464 (9)	0.0837 (13)	0.0567 (10)	0.0132 (9)	0.0010 (7)	−0.0188 (9)
C14	0.0606 (11)	0.1010 (17)	0.0817 (14)	0.0389 (12)	−0.0100 (10)	−0.0405 (13)
C15	0.0844 (14)	0.0631 (12)	0.0880 (14)	0.0378 (11)	−0.0288 (12)	−0.0299 (11)
C16	0.0730 (11)	0.0420 (9)	0.0589 (10)	0.0140 (8)	−0.0235 (8)	−0.0121 (7)
C17	0.0380 (7)	0.0338 (7)	0.0426 (7)	−0.0026 (6)	0.0003 (6)	0.0013 (6)
C18	0.0387 (7)	0.0370 (8)	0.0668 (10)	−0.0028 (6)	−0.0044 (7)	−0.0008 (7)
C19	0.0484 (9)	0.0404 (8)	0.0813 (12)	0.0056 (7)	−0.0079 (8)	−0.0006 (8)
C20	0.0603 (11)	0.0398 (9)	0.1291 (19)	−0.0094 (8)	−0.0204 (11)	−0.0138 (10)
C21	0.0433 (8)	0.0423 (9)	0.0873 (13)	−0.0028 (7)	−0.0129 (8)	−0.0065 (8)
C22	0.0372 (7)	0.0355 (7)	0.0385 (7)	−0.0018 (5)	−0.0013 (5)	−0.0025 (6)
C23	0.0600 (9)	0.0524 (9)	0.0414 (8)	−0.0006 (7)	−0.0028 (7)	0.0126 (7)
C24	0.0885 (13)	0.0532 (10)	0.0555 (10)	0.0116 (9)	0.0022 (9)	0.0108 (8)
N1	0.0656 (10)	0.0358 (7)	0.1119 (14)	0.0022 (7)	−0.0146 (9)	−0.0070 (8)
O1	0.0444 (6)	0.0500 (6)	0.0476 (6)	−0.0064 (5)	−0.0044 (4)	0.0145 (5)
O2	0.0502 (7)	0.0725 (8)	0.0651 (7)	−0.0186 (6)	−0.0210 (5)	0.0209 (6)

C1—C2	1.382 (2)	C13—C14	1.386 (3)
C1—C6	1.392 (2)	C13—H13	0.9300
C1—C10	1.5097 (19)	C14—C15	1.370 (3)
C2—C3	1.389 (2)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.381 (3)
C3—C4	1.372 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.376 (3)	C17—C21	1.378 (2)
C4—H4	0.9300	C17—C18	1.385 (2)
C5—C6	1.380 (2)	C18—C19	1.376 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.513 (2)	C19—N1	1.325 (2)
C7—C12	1.510 (2)	C19—H19	0.9300
C7—C8	1.5695 (19)	C20—N1	1.326 (2)
C7—H7	0.9800	C20—C21	1.377 (2)
C8—C17	1.5089 (19)	C20—H20	0.9300
C8—C9	1.5460 (17)	C21—H21	0.9300
C8—H8	0.9800	C22—O2	1.1952 (17)
C9—C22	1.5180 (18)	C22—O1	1.3258 (16)
C9—C10	1.5693 (18)	C23—O1	1.4538 (17)
C9—H9	0.9800	C23—C24	1.487 (2)
C10—C11	1.508 (2)	C23—H23A	0.9700
C10—H10	0.9800	C23—H23B	0.9700
C11—C16	1.383 (2)	C24—H24A	0.9600
C11—C12	1.389 (2)	C24—H24B	0.9600
C12—C13	1.382 (2)	C24—H24C	0.9600
C2—C1—C6	120.50 (14)	C13—C12—C7	126.37 (16)
C2—C1—C10	126.33 (13)	C11—C12—C7	113.46 (12)
C6—C1—C10	113.17 (12)	C12—C13—C14	118.5 (2)
C1—C2—C3	119.01 (16)	C12—C13—H13	120.7
C1—C2—H2	120.5	C14—C13—H13	120.7
C3—C2—H2	120.5	C15—C14—C13	121.14 (18)
C4—C3—C2	120.41 (16)	C15—C14—H14	119.4
C4—C3—H3	119.8	C13—C14—H14	119.4
C2—C3—H3	119.8	C14—C15—C16	120.74 (18)
C3—C4—C5	120.54 (16)	C14—C15—H15	119.6
C3—C4—H4	119.7	C16—C15—H15	119.6
C5—C4—H4	119.7	C15—C16—C11	118.55 (19)
C4—C5—C6	119.96 (17)	C15—C16—H16	120.7
C4—C5—H5	120.0	C11—C16—H16	120.7
C6—C5—H5	120.0	C21—C17—C18	116.18 (13)
C5—C6—C1	119.57 (14)	C21—C17—C8	119.60 (13)
C5—C6—C7	127.44 (14)	C18—C17—C8	124.18 (12)
C1—C6—C7	112.98 (12)	C19—C18—C17	119.94 (14)
C12—C7—C6	107.38 (12)	C19—C18—H18	120.0
C12—C7—C8	105.63 (11)	C17—C18—H18	120.0
C6—C7—C8	108.25 (11)	N1—C19—C18	124.26 (15)
C12—C7—H7	111.8	N1—C19—H19	117.9
C6—C7—H7	111.8	C18—C19—H19	117.9
C8—C7—H7	111.8	N1—C20—C21	124.93 (16)
C17—C8—C9	115.20 (11)	N1—C20—H20	117.5
C17—C8—C7	111.08 (11)	C21—C20—H20	117.5
C9—C8—C7	108.42 (10)	C20—C21—C17	119.42 (15)
C17—C8—H8	107.3	C20—C21—H21	120.3
C9—C8—H8	107.3	C17—C21—H21	120.3
C7—C8—H8	107.3	O2—C22—O1	123.76 (13)
C22—C9—C8	112.21 (10)	O2—C22—C9	125.88 (13)
C22—C9—C10	110.35 (11)	O1—C22—C9	110.36 (11)
C8—C9—C10	109.87 (11)	O1—C23—C24	110.02 (13)
C22—C9—H9	108.1	O1—C23—H23A	109.7
C8—C9—H9	108.1	C24—C23—H23A	109.7
C10—C9—H9	108.1	O1—C23—H23B	109.7
C11—C10—C1	107.48 (11)	C24—C23—H23B	109.7
C11—C10—C9	106.99 (11)	H23A—C23—H23B	108.2
C1—C10—C9	106.37 (11)	C23—C24—H24A	109.5
C11—C10—H10	111.9	C23—C24—H24B	109.5
C1—C10—H10	111.9	H24A—C24—H24B	109.5
C9—C10—H10	111.9	C23—C24—H24C	109.5
C16—C11—C12	120.81 (15)	H24A—C24—H24C	109.5
C16—C11—C10	126.33 (15)	H24B—C24—H24C	109.5
C12—C11—C10	112.86 (12)	C19—N1—C20	115.26 (14)
C13—C12—C11	120.17 (15)	C22—O1—C23	117.80 (11)
C6—C1—C2—C3	0.9 (2)	C16—C11—C12—C13	−1.3 (2)
C10—C1—C2—C3	−179.47 (14)	C10—C11—C12—C13	178.93 (13)
C1—C2—C3—C4	−0.7 (3)	C16—C11—C12—C7	178.95 (13)
C2—C3—C4—C5	−0.2 (3)	C10—C11—C12—C7	−0.77 (17)
C3—C4—C5—C6	0.9 (3)	C6—C7—C12—C13	126.43 (16)
C4—C5—C6—C1	−0.7 (2)	C8—C7—C12—C13	−118.21 (16)
C4—C5—C6—C7	179.87 (16)	C6—C7—C12—C11	−53.89 (15)
C2—C1—C6—C5	−0.2 (2)	C8—C7—C12—C11	61.47 (14)
C10—C1—C6—C5	−179.89 (13)	C11—C12—C13—C14	2.1 (2)
C2—C1—C6—C7	179.33 (13)	C7—C12—C13—C14	−178.20 (15)
C10—C1—C6—C7	−0.36 (17)	C12—C13—C14—C15	−1.0 (3)
C5—C6—C7—C12	−126.13 (16)	C13—C14—C15—C16	−1.0 (3)
C1—C6—C7—C12	54.38 (15)	C14—C15—C16—C11	1.8 (3)
C5—C6—C7—C8	120.26 (16)	C12—C11—C16—C15	−0.6 (2)
C1—C6—C7—C8	−59.23 (15)	C10—C11—C16—C15	179.04 (15)
C12—C7—C8—C17	172.86 (11)	C9—C8—C17—C21	135.65 (15)
C6—C7—C8—C17	−72.38 (14)	C7—C8—C17—C21	−100.59 (16)
C12—C7—C8—C9	−59.59 (13)	C9—C8—C17—C18	−46.84 (19)
C6—C7—C8—C9	55.17 (14)	C7—C8—C17—C18	76.93 (17)
C17—C8—C9—C22	−109.03 (13)	C21—C17—C18—C19	0.4 (2)
C7—C8—C9—C22	125.81 (12)	C8—C17—C18—C19	−177.20 (15)
C17—C8—C9—C10	127.81 (12)	C17—C18—C19—N1	0.2 (3)
C7—C8—C9—C10	2.65 (14)	N1—C20—C21—C17	1.0 (4)
C2—C1—C10—C11	125.88 (15)	C18—C17—C21—C20	−0.9 (3)
C6—C1—C10—C11	−54.46 (15)	C8—C17—C21—C20	176.79 (17)
C2—C1—C10—C9	−119.80 (15)	C8—C9—C22—O2	−0.6 (2)
C6—C1—C10—C9	59.86 (14)	C10—C9—C22—O2	122.24 (16)
C22—C9—C10—C11	−68.66 (14)	C8—C9—C22—O1	−179.85 (11)
C8—C9—C10—C11	55.59 (14)	C10—C9—C22—O1	−56.96 (14)
C22—C9—C10—C1	176.69 (11)	C18—C19—N1—C20	−0.1 (3)
C8—C9—C10—C1	−59.07 (13)	C21—C20—N1—C19	−0.4 (3)
C1—C10—C11—C16	−124.66 (15)	O2—C22—O1—C23	−4.4 (2)
C9—C10—C11—C16	121.43 (15)	C9—C22—O1—C23	174.85 (12)
C1—C10—C11—C12	55.04 (15)	C24—C23—O1—C22	−83.74 (17)
C9—C10—C11—C12	−58.87 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.93	2.55	3.2612 (18)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1i	0.93	2.55	3.2612 (18)	134

Symmetry code: (i) .