C—H...π interactions in 9-(n-do­decylamino­methyl)­anthracene

The title compound, C₂₇H₃₇N, which is intended to be included in the structure of a sulfon­amide porphyrin for the preparation of Langmuir–Blodgett films, consists of a do­decyl chain linked to an anthracene mol­ecule through an amino­methyl group. The angle between the least-squares plane of the anthracene and the do­decyl chain is 11.44 (8)°. The mol­ecules are arranged in zigzag layers head-to-head, with the hydro­carbon chains side-by-side. The structure is stabilized by C—H...π interactions, the strongest having an H...centroid distance of 2.63 Å.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

9-(n-dodecylaminomethyl)anthracene

Crystal data

C27H37N	Dx = 1.091 Mg m^−3
Mr = 375.58	Cu Kα radiation, λ = 1.54056 Å
Orthorhombic, Pccn	Cell parameters from 25 reflections
a = 17.760 (9) Å	θ = 11.5–21.9°
b = 32.336 (11) Å	µ = 0.46 mm^−1
c = 7.9664 (6) Å	T = 293 K
V = 4575 (3) Å^3	Block, translucent pale yellow
Z = 8	0.51 × 0.34 × 0.25 mm
F(000) = 1648

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.049
Radiation source: rotating anode generator	θmax = 67.3°, θmin = 4.8°
Graphite monochromator	h = −2→21
profile data from ω–θ scans	k = −4→38
4111 measured reflections	l = 0→9
4103 independent reflections	2 standard reflections every 180 min
3069 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.1039P)^2 + 1.0675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4108 reflections	Δρmax = 0.32 e Å^−3
258 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00053 (14)

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
N12	0.11720 (10)	0.15238 (5)	0.4914 (2)	0.0564 (4)
H12	0.0818 (14)	0.1707 (8)	0.442 (3)	0.085*
C1	0.14969 (11)	0.17500 (6)	0.8852 (2)	0.0548 (5)
H1	0.1754	0.1578	0.8113	0.066*
C2	0.18779 (12)	0.19274 (7)	1.0136 (3)	0.0646 (6)
H2	0.2391	0.1879	1.0258	0.077*
C3	0.14993 (13)	0.21852 (7)	1.1292 (3)	0.0672 (6)
H3	0.1763	0.2305	1.2176	0.081*
C4	0.07576 (13)	0.22587 (6)	1.1118 (2)	0.0598 (5)
H4	0.0514	0.2425	1.1901	0.072*
C4A	0.03378 (11)	0.20879 (5)	0.9763 (2)	0.0457 (4)
C5	−0.15867 (11)	0.21353 (6)	0.7887 (3)	0.0588 (5)
H5	−0.1827	0.2309	0.8645	0.071*
C6	−0.19728 (12)	0.19881 (7)	0.6556 (3)	0.0677 (6)
H6	−0.2477	0.2057	0.6414	0.081*
C7	−0.16124 (13)	0.17312 (7)	0.5387 (3)	0.0678 (6)
H7	−0.1879	0.1635	0.4461	0.081*
C8	−0.08833 (12)	0.16207 (6)	0.5582 (3)	0.0585 (5)
H8	−0.0659	0.1450	0.4785	0.070*
C8A	−0.04489 (10)	0.17590 (5)	0.6984 (2)	0.0453 (4)
C9	0.03062 (10)	0.16442 (5)	0.7260 (2)	0.0460 (4)
C9A	0.07136 (10)	0.18191 (5)	0.8600 (2)	0.0442 (4)
C10	−0.04173 (11)	0.21816 (5)	0.9515 (2)	0.0504 (5)
H10	−0.0662	0.2351	1.0284	0.060*
C10A	−0.08156 (10)	0.20290 (5)	0.8152 (2)	0.0462 (4)
C11	0.06876 (11)	0.13273 (5)	0.6135 (2)	0.0518 (5)
H11A	0.0983	0.1140	0.6819	0.062*
H11B	0.0307	0.1166	0.5556	0.062*
C13	0.15351 (11)	0.12255 (7)	0.3788 (3)	0.0596 (5)
H13A	0.1791	0.1021	0.4472	0.072*
H13B	0.1917	0.1371	0.3148	0.072*
C14	0.10276 (10)	0.09979 (6)	0.2557 (2)	0.0539 (5)
H14A	0.0680	0.0824	0.3177	0.065*
H14B	0.0734	0.1198	0.1928	0.065*
C15	0.14756 (11)	0.07328 (6)	0.1345 (2)	0.0531 (5)
H15A	0.1860	0.0903	0.0825	0.064*
H15B	0.1728	0.0517	0.1974	0.064*
C16	0.10052 (10)	0.05344 (6)	−0.0022 (2)	0.0504 (4)
H16A	0.0712	0.0747	−0.0577	0.061*
H16B	0.0656	0.0341	0.0490	0.061*
C17	0.14694 (10)	0.03063 (6)	−0.1329 (2)	0.0539 (5)
H17A	0.1832	0.0497	−0.1809	0.065*
H17B	0.1749	0.0088	−0.0777	0.065*
C18	0.10071 (10)	0.01187 (6)	−0.2738 (2)	0.0520 (5)
H18A	0.0652	−0.0077	−0.2262	0.062*
H18B	0.0720	0.0336	−0.3279	0.062*
C19	0.14785 (11)	−0.01014 (7)	−0.4051 (3)	0.0577 (5)
H19A	0.1845	0.0092	−0.4496	0.069*
H19B	0.1754	−0.0324	−0.3511	0.069*
C20	0.10311 (10)	−0.02803 (6)	−0.5500 (2)	0.0534 (5)
H20A	0.0657	−0.0469	−0.5057	0.064*
H20B	0.0766	−0.0058	−0.6063	0.064*
C21	0.15080 (10)	−0.05078 (6)	−0.6776 (3)	0.0565 (5)
H21A	0.1760	−0.0736	−0.6215	0.068*
H21B	0.1894	−0.0321	−0.7183	0.068*
C22	0.10797 (10)	−0.06775 (6)	−0.8270 (2)	0.0513 (5)
H22A	0.0672	−0.0851	−0.7866	0.062*
H22B	0.0858	−0.0449	−0.8883	0.062*
C23	0.15623 (13)	−0.09268 (7)	−0.9454 (3)	0.0687 (6)
H23A	0.1783	−0.1156	−0.8839	0.082*
H23B	0.1971	−0.0754	−0.9851	0.082*
C24	0.11417 (17)	−0.10973 (8)	−1.0959 (3)	0.0855 (8)
H24A	0.0743	−0.1275	−1.0581	0.128*
H24B	0.1482	−0.1252	−1.1651	0.128*
H24C	0.0934	−0.0873	−1.1597	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N12	0.0650 (10)	0.0538 (9)	0.0503 (9)	−0.0041 (8)	0.0100 (8)	−0.0081 (7)
C1	0.0561 (11)	0.0589 (11)	0.0493 (11)	0.0090 (9)	0.0012 (9)	−0.0036 (9)
C2	0.0600 (12)	0.0734 (13)	0.0603 (12)	0.0033 (10)	−0.0065 (10)	−0.0007 (11)
C3	0.0758 (15)	0.0699 (13)	0.0558 (12)	−0.0027 (11)	−0.0132 (11)	−0.0100 (11)
C4	0.0779 (14)	0.0539 (11)	0.0477 (11)	0.0044 (9)	−0.0034 (10)	−0.0118 (8)
C4A	0.0606 (10)	0.0369 (8)	0.0395 (9)	0.0024 (7)	0.0034 (8)	−0.0019 (7)
C5	0.0575 (11)	0.0582 (11)	0.0607 (12)	0.0106 (9)	0.0069 (10)	0.0051 (10)
C6	0.0567 (12)	0.0713 (13)	0.0751 (15)	0.0055 (10)	−0.0048 (11)	0.0101 (12)
C7	0.0691 (13)	0.0698 (13)	0.0646 (13)	−0.0034 (11)	−0.0149 (11)	−0.0016 (11)
C8	0.0680 (12)	0.0558 (11)	0.0517 (11)	−0.0003 (9)	−0.0035 (10)	−0.0073 (9)
C8A	0.0557 (10)	0.0390 (8)	0.0413 (9)	−0.0002 (7)	0.0031 (8)	0.0000 (7)
C9	0.0557 (10)	0.0402 (8)	0.0422 (9)	0.0024 (7)	0.0053 (8)	−0.0035 (7)
C9A	0.0541 (10)	0.0387 (8)	0.0397 (9)	0.0038 (7)	0.0033 (7)	−0.0003 (7)
C10	0.0637 (11)	0.0438 (9)	0.0437 (10)	0.0092 (8)	0.0089 (8)	−0.0055 (8)
C10A	0.0529 (10)	0.0405 (9)	0.0451 (10)	0.0032 (7)	0.0073 (8)	0.0032 (7)
C11	0.0633 (11)	0.0452 (9)	0.0469 (10)	−0.0003 (8)	0.0072 (8)	−0.0029 (8)
C13	0.0521 (11)	0.0736 (13)	0.0530 (11)	−0.0006 (9)	0.0048 (9)	−0.0204 (10)
C14	0.0485 (9)	0.0645 (12)	0.0487 (10)	0.0018 (8)	0.0035 (8)	−0.0138 (9)
C15	0.0519 (10)	0.0603 (11)	0.0472 (10)	0.0047 (8)	0.0018 (8)	−0.0119 (8)
C16	0.0523 (10)	0.0536 (10)	0.0454 (10)	0.0026 (8)	0.0018 (8)	−0.0086 (8)
C17	0.0518 (10)	0.0612 (11)	0.0488 (11)	0.0035 (9)	0.0019 (8)	−0.0139 (9)
C18	0.0504 (10)	0.0549 (10)	0.0507 (10)	0.0027 (8)	0.0005 (8)	−0.0111 (9)
C19	0.0506 (10)	0.0683 (12)	0.0541 (11)	0.0004 (9)	−0.0003 (9)	−0.0178 (10)
C20	0.0513 (10)	0.0573 (10)	0.0517 (11)	0.0001 (8)	−0.0011 (8)	−0.0127 (9)
C21	0.0504 (10)	0.0628 (11)	0.0564 (12)	−0.0007 (9)	0.0010 (9)	−0.0166 (10)
C22	0.0558 (10)	0.0494 (10)	0.0487 (10)	−0.0029 (8)	0.0007 (8)	−0.0061 (8)
C23	0.0711 (14)	0.0751 (14)	0.0598 (13)	0.0001 (11)	0.0066 (10)	−0.0204 (11)
C24	0.124 (2)	0.0765 (15)	0.0564 (13)	−0.0018 (14)	0.0002 (14)	−0.0207 (12)

Geometric parameters (Å, º)

N12—C11	1.446 (2)	C14—C15	1.517 (2)
N12—C13	1.467 (2)	C14—H14A	0.9700
N12—H12	0.95 (3)	C14—H14B	0.9700
C1—C2	1.354 (3)	C15—C16	1.515 (2)
C1—C9A	1.423 (3)	C15—H15A	0.9700
C1—H1	0.9300	C15—H15B	0.9700
C2—C3	1.412 (3)	C16—C17	1.519 (2)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.346 (3)	C16—H16B	0.9700
C3—H3	0.9300	C17—C18	1.517 (3)
C4—C4A	1.424 (3)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C4A—C10	1.389 (3)	C18—C19	1.517 (3)
C4A—C9A	1.435 (2)	C18—H18A	0.9700
C5—C6	1.349 (3)	C18—H18B	0.9700
C5—C10A	1.428 (3)	C19—C20	1.516 (3)
C5—H5	0.9300	C19—H19A	0.9700
C6—C7	1.403 (3)	C19—H19B	0.9700
C6—H6	0.9300	C20—C21	1.514 (2)
C7—C8	1.352 (3)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—C8A	1.429 (3)	C21—C22	1.515 (3)
C8—H8	0.9300	C21—H21A	0.9700
C8A—C9	1.409 (3)	C21—H21B	0.9700
C8A—C10A	1.432 (2)	C22—C23	1.508 (3)
C9—C9A	1.408 (2)	C22—H22A	0.9700
C9—C11	1.521 (2)	C22—H22B	0.9700
C10—C10A	1.387 (3)	C23—C24	1.516 (3)
C10—H10	0.9300	C23—H23A	0.9700
C11—H11A	0.9700	C23—H23B	0.9700
C11—H11B	0.9700	C24—H24A	0.9600
C13—C14	1.521 (3)	C24—H24B	0.9600
C13—H13A	0.9700	C24—H24C	0.9600
C13—H13B	0.9700
C11—N12—C13	112.59 (16)	H14A—C14—H14B	107.9
C11—N12—H12	99.2 (15)	C16—C15—C14	114.07 (16)
C13—N12—H12	116.4 (16)	C16—C15—H15A	108.7
C2—C1—C9A	121.89 (18)	C14—C15—H15A	108.7
C2—C1—H1	119.1	C16—C15—H15B	108.7
C9A—C1—H1	119.1	C14—C15—H15B	108.7
C1—C2—C3	120.30 (19)	H15A—C15—H15B	107.6
C1—C2—H2	119.8	C15—C16—C17	113.52 (15)
C3—C2—H2	119.8	C15—C16—H16A	108.9
C4—C3—C2	120.23 (19)	C17—C16—H16A	108.9
C4—C3—H3	119.9	C15—C16—H16B	108.9
C2—C3—H3	119.9	C17—C16—H16B	108.9
C3—C4—C4A	121.47 (19)	H16A—C16—H16B	107.7
C3—C4—H4	119.3	C18—C17—C16	114.04 (15)
C4A—C4—H4	119.3	C18—C17—H17A	108.7
C10—C4A—C4	121.90 (17)	C16—C17—H17A	108.7
C10—C4A—C9A	119.33 (16)	C18—C17—H17B	108.7
C4—C4A—C9A	118.75 (17)	C16—C17—H17B	108.7
C6—C5—C10A	121.3 (2)	H17A—C17—H17B	107.6
C6—C5—H5	119.4	C19—C18—C17	113.52 (16)
C10A—C5—H5	119.4	C19—C18—H18A	108.9
C5—C6—C7	119.9 (2)	C17—C18—H18A	108.9
C5—C6—H6	120.0	C19—C18—H18B	108.9
C7—C6—H6	120.0	C17—C18—H18B	108.9
C8—C7—C6	121.1 (2)	H18A—C18—H18B	107.7
C8—C7—H7	119.4	C20—C19—C18	114.51 (16)
C6—C7—H7	119.4	C20—C19—H19A	108.6
C7—C8—C8A	121.6 (2)	C18—C19—H19A	108.6
C7—C8—H8	119.2	C20—C19—H19B	108.6
C8A—C8—H8	119.2	C18—C19—H19B	108.6
C9—C8A—C8	123.59 (17)	H19A—C19—H19B	107.6
C9—C8A—C10A	119.48 (16)	C21—C20—C19	113.79 (16)
C8—C8A—C10A	116.93 (17)	C21—C20—H20A	108.8
C9A—C9—C8A	120.10 (15)	C19—C20—H20A	108.8
C9A—C9—C11	119.25 (16)	C21—C20—H20B	108.8
C8A—C9—C11	120.64 (16)	C19—C20—H20B	108.8
C9—C9A—C1	123.09 (16)	H20A—C20—H20B	107.7
C9—C9A—C4A	119.58 (16)	C20—C21—C22	114.98 (16)
C1—C9A—C4A	117.32 (16)	C20—C21—H21A	108.5
C10A—C10—C4A	121.73 (16)	C22—C21—H21A	108.5
C10A—C10—H10	119.1	C20—C21—H21B	108.5
C4A—C10—H10	119.1	C22—C21—H21B	108.5
C10—C10A—C5	121.31 (17)	H21A—C21—H21B	107.5
C10—C10A—C8A	119.57 (17)	C23—C22—C21	113.55 (17)
C5—C10A—C8A	119.12 (18)	C23—C22—H22A	108.9
N12—C11—C9	111.44 (14)	C21—C22—H22A	108.9
N12—C11—H11A	109.3	C23—C22—H22B	108.9
C9—C11—H11A	109.3	C21—C22—H22B	108.9
N12—C11—H11B	109.3	H22A—C22—H22B	107.7
C9—C11—H11B	109.3	C22—C23—C24	114.1 (2)
H11A—C11—H11B	108.0	C22—C23—H23A	108.7
N12—C13—C14	116.86 (16)	C24—C23—H23A	108.7
N12—C13—H13A	108.1	C22—C23—H23B	108.7
C14—C13—H13A	108.1	C24—C23—H23B	108.7
N12—C13—H13B	108.1	H23A—C23—H23B	107.6
C14—C13—H13B	108.1	C23—C24—H24A	109.5
H13A—C13—H13B	107.3	C23—C24—H24B	109.5
C15—C14—C13	111.89 (15)	H24A—C24—H24B	109.5
C15—C14—H14A	109.2	C23—C24—H24C	109.5
C13—C14—H14A	109.2	H24A—C24—H24C	109.5
C15—C14—H14B	109.2	H24B—C24—H24C	109.5
C13—C14—H14B	109.2
C9A—C1—C2—C3	0.9 (3)	C4—C4A—C10—C10A	177.14 (17)
C1—C2—C3—C4	−0.4 (3)	C9A—C4A—C10—C10A	−1.4 (3)
C2—C3—C4—C4A	−1.2 (3)	C4A—C10—C10A—C5	−178.43 (17)
C3—C4—C4A—C10	−176.1 (2)	C4A—C10—C10A—C8A	1.6 (3)
C3—C4—C4A—C9A	2.4 (3)	C6—C5—C10A—C10	179.71 (18)
C10A—C5—C6—C7	−1.1 (3)	C6—C5—C10A—C8A	−0.3 (3)
C5—C6—C7—C8	1.2 (3)	C9—C8A—C10A—C10	1.6 (3)
C6—C7—C8—C8A	0.1 (3)	C8—C8A—C10A—C10	−178.41 (16)
C7—C8—C8A—C9	178.48 (19)	C9—C8A—C10A—C5	−178.41 (16)
C7—C8—C8A—C10A	−1.5 (3)	C8—C8A—C10A—C5	1.6 (2)
C8—C8A—C9—C9A	175.05 (16)	C13—N12—C11—C9	−178.79 (16)
C10A—C8A—C9—C9A	−4.9 (3)	C9A—C9—C11—N12	−79.3 (2)
C8—C8A—C9—C11	−5.7 (3)	C8A—C9—C11—N12	101.5 (2)
C10A—C8A—C9—C11	174.30 (15)	C11—N12—C13—C14	68.2 (2)
C8A—C9—C9A—C1	−173.44 (17)	N12—C13—C14—C15	174.07 (17)
C11—C9—C9A—C1	7.3 (3)	C13—C14—C15—C16	−173.95 (17)
C8A—C9—C9A—C4A	5.2 (3)	C14—C15—C16—C17	174.07 (17)
C11—C9—C9A—C4A	−174.08 (15)	C15—C16—C17—C18	−178.00 (16)
C2—C1—C9A—C9	178.93 (18)	C16—C17—C18—C19	178.94 (17)
C2—C1—C9A—C4A	0.3 (3)	C17—C18—C19—C20	−178.23 (17)
C10—C4A—C9A—C9	−2.0 (2)	C18—C19—C20—C21	−178.56 (17)
C4—C4A—C9A—C9	179.42 (16)	C19—C20—C21—C22	−178.01 (17)
C10—C4A—C9A—C1	176.65 (17)	C20—C21—C22—C23	−176.08 (18)
C4—C4A—C9A—C1	−1.9 (2)	C21—C22—C23—C24	−179.79 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg(1)^i	0.93	3.35	3.984 (3)	127
C4—H4···Cg(2)^i	0.93	2.63	3.518 (3)	161
C10—H10···Cg(3)^i	0.93	2.93	3.806 (2)	158
C14—H14B···Cg(1)^ii	0.97	3.12	3.860 (2)	135
C23—H23A···Cg(3)^iii	0.97	3.03	3.798 (3)	137
C24—H24A···Cg(2)^iii	0.96	2.99	3.877 (3)	155

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