Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008441/gd1095sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008441/gd1095Isup2.hkl
Contains datablock I

CCDC reference: 150850

Computing details top

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 top
Crystal data top
C27H37NDx = 1.091 Mg m3
Mr = 375.58Cu Kα radiation, λ = 1.54056 Å
Orthorhombic, PccnCell parameters from 25 reflections
a = 17.760 (9) Åθ = 11.5–21.9°
b = 32.336 (11) ŵ = 0.46 mm1
c = 7.9664 (6) ÅT = 293 K
V = 4575 (3) Å3Block, translucent pale yellow
Z = 80.51 × 0.34 × 0.25 mm
F(000) = 1648
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.049
Radiation source: rotating anode generatorθmax = 67.3°, θmin = 4.8°
Graphite monochromatorh = 221
profile data from ωθ scansk = 438
4111 measured reflectionsl = 09
4103 independent reflections2 standard reflections every 180 min
3069 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.187 w = 1/[σ2(Fo2) + (0.1039P)2 + 1.0675P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
4108 reflectionsΔρmax = 0.32 e Å3
258 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00053 (14)
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
xyzUiso*/Ueq
N120.11720 (10)0.15238 (5)0.4914 (2)0.0564 (4)
H120.0818 (14)0.1707 (8)0.442 (3)0.085*
C10.14969 (11)0.17500 (6)0.8852 (2)0.0548 (5)
H10.17540.15780.81130.066*
C20.18779 (12)0.19274 (7)1.0136 (3)0.0646 (6)
H20.23910.18791.02580.077*
C30.14993 (13)0.21852 (7)1.1292 (3)0.0672 (6)
H30.17630.23051.21760.081*
C40.07576 (13)0.22587 (6)1.1118 (2)0.0598 (5)
H40.05140.24251.19010.072*
C4A0.03378 (11)0.20879 (5)0.9763 (2)0.0457 (4)
C50.15867 (11)0.21353 (6)0.7887 (3)0.0588 (5)
H50.18270.23090.86450.071*
C60.19728 (12)0.19881 (7)0.6556 (3)0.0677 (6)
H60.24770.20570.64140.081*
C70.16124 (13)0.17312 (7)0.5387 (3)0.0678 (6)
H70.18790.16350.44610.081*
C80.08833 (12)0.16207 (6)0.5582 (3)0.0585 (5)
H80.06590.14500.47850.070*
C8A0.04489 (10)0.17590 (5)0.6984 (2)0.0453 (4)
C90.03062 (10)0.16442 (5)0.7260 (2)0.0460 (4)
C9A0.07136 (10)0.18191 (5)0.8600 (2)0.0442 (4)
C100.04173 (11)0.21816 (5)0.9515 (2)0.0504 (5)
H100.06620.23511.02840.060*
C10A0.08156 (10)0.20290 (5)0.8152 (2)0.0462 (4)
C110.06876 (11)0.13273 (5)0.6135 (2)0.0518 (5)
H11A0.09830.11400.68190.062*
H11B0.03070.11660.55560.062*
C130.15351 (11)0.12255 (7)0.3788 (3)0.0596 (5)
H13A0.17910.10210.44720.072*
H13B0.19170.13710.31480.072*
C140.10276 (10)0.09979 (6)0.2557 (2)0.0539 (5)
H14A0.06800.08240.31770.065*
H14B0.07340.11980.19280.065*
C150.14756 (11)0.07328 (6)0.1345 (2)0.0531 (5)
H15A0.18600.09030.08250.064*
H15B0.17280.05170.19740.064*
C160.10052 (10)0.05344 (6)0.0022 (2)0.0504 (4)
H16A0.07120.07470.05770.061*
H16B0.06560.03410.04900.061*
C170.14694 (10)0.03063 (6)0.1329 (2)0.0539 (5)
H17A0.18320.04970.18090.065*
H17B0.17490.00880.07770.065*
C180.10071 (10)0.01187 (6)0.2738 (2)0.0520 (5)
H18A0.06520.00770.22620.062*
H18B0.07200.03360.32790.062*
C190.14785 (11)0.01014 (7)0.4051 (3)0.0577 (5)
H19A0.18450.00920.44960.069*
H19B0.17540.03240.35110.069*
C200.10311 (10)0.02803 (6)0.5500 (2)0.0534 (5)
H20A0.06570.04690.50570.064*
H20B0.07660.00580.60630.064*
C210.15080 (10)0.05078 (6)0.6776 (3)0.0565 (5)
H21A0.17600.07360.62150.068*
H21B0.18940.03210.71830.068*
C220.10797 (10)0.06775 (6)0.8270 (2)0.0513 (5)
H22A0.06720.08510.78660.062*
H22B0.08580.04490.88830.062*
C230.15623 (13)0.09268 (7)0.9454 (3)0.0687 (6)
H23A0.17830.11560.88390.082*
H23B0.19710.07540.98510.082*
C240.11417 (17)0.10973 (8)1.0959 (3)0.0855 (8)
H24A0.07430.12751.05810.128*
H24B0.14820.12521.16510.128*
H24C0.09340.08731.15970.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N120.0650 (10)0.0538 (9)0.0503 (9)0.0041 (8)0.0100 (8)0.0081 (7)
C10.0561 (11)0.0589 (11)0.0493 (11)0.0090 (9)0.0012 (9)0.0036 (9)
C20.0600 (12)0.0734 (13)0.0603 (12)0.0033 (10)0.0065 (10)0.0007 (11)
C30.0758 (15)0.0699 (13)0.0558 (12)0.0027 (11)0.0132 (11)0.0100 (11)
C40.0779 (14)0.0539 (11)0.0477 (11)0.0044 (9)0.0034 (10)0.0118 (8)
C4A0.0606 (10)0.0369 (8)0.0395 (9)0.0024 (7)0.0034 (8)0.0019 (7)
C50.0575 (11)0.0582 (11)0.0607 (12)0.0106 (9)0.0069 (10)0.0051 (10)
C60.0567 (12)0.0713 (13)0.0751 (15)0.0055 (10)0.0048 (11)0.0101 (12)
C70.0691 (13)0.0698 (13)0.0646 (13)0.0034 (11)0.0149 (11)0.0016 (11)
C80.0680 (12)0.0558 (11)0.0517 (11)0.0003 (9)0.0035 (10)0.0073 (9)
C8A0.0557 (10)0.0390 (8)0.0413 (9)0.0002 (7)0.0031 (8)0.0000 (7)
C90.0557 (10)0.0402 (8)0.0422 (9)0.0024 (7)0.0053 (8)0.0035 (7)
C9A0.0541 (10)0.0387 (8)0.0397 (9)0.0038 (7)0.0033 (7)0.0003 (7)
C100.0637 (11)0.0438 (9)0.0437 (10)0.0092 (8)0.0089 (8)0.0055 (8)
C10A0.0529 (10)0.0405 (9)0.0451 (10)0.0032 (7)0.0073 (8)0.0032 (7)
C110.0633 (11)0.0452 (9)0.0469 (10)0.0003 (8)0.0072 (8)0.0029 (8)
C130.0521 (11)0.0736 (13)0.0530 (11)0.0006 (9)0.0048 (9)0.0204 (10)
C140.0485 (9)0.0645 (12)0.0487 (10)0.0018 (8)0.0035 (8)0.0138 (9)
C150.0519 (10)0.0603 (11)0.0472 (10)0.0047 (8)0.0018 (8)0.0119 (8)
C160.0523 (10)0.0536 (10)0.0454 (10)0.0026 (8)0.0018 (8)0.0086 (8)
C170.0518 (10)0.0612 (11)0.0488 (11)0.0035 (9)0.0019 (8)0.0139 (9)
C180.0504 (10)0.0549 (10)0.0507 (10)0.0027 (8)0.0005 (8)0.0111 (9)
C190.0506 (10)0.0683 (12)0.0541 (11)0.0004 (9)0.0003 (9)0.0178 (10)
C200.0513 (10)0.0573 (10)0.0517 (11)0.0001 (8)0.0011 (8)0.0127 (9)
C210.0504 (10)0.0628 (11)0.0564 (12)0.0007 (9)0.0010 (9)0.0166 (10)
C220.0558 (10)0.0494 (10)0.0487 (10)0.0029 (8)0.0007 (8)0.0061 (8)
C230.0711 (14)0.0751 (14)0.0598 (13)0.0001 (11)0.0066 (10)0.0204 (11)
C240.124 (2)0.0765 (15)0.0564 (13)0.0018 (14)0.0002 (14)0.0207 (12)
Geometric parameters (Å, º) top
N12—C111.446 (2)C14—C151.517 (2)
N12—C131.467 (2)C14—H14A0.9700
N12—H120.95 (3)C14—H14B0.9700
C1—C21.354 (3)C15—C161.515 (2)
C1—C9A1.423 (3)C15—H15A0.9700
C1—H10.9300C15—H15B0.9700
C2—C31.412 (3)C16—C171.519 (2)
C2—H20.9300C16—H16A0.9700
C3—C41.346 (3)C16—H16B0.9700
C3—H30.9300C17—C181.517 (3)
C4—C4A1.424 (3)C17—H17A0.9700
C4—H40.9300C17—H17B0.9700
C4A—C101.389 (3)C18—C191.517 (3)
C4A—C9A1.435 (2)C18—H18A0.9700
C5—C61.349 (3)C18—H18B0.9700
C5—C10A1.428 (3)C19—C201.516 (3)
C5—H50.9300C19—H19A0.9700
C6—C71.403 (3)C19—H19B0.9700
C6—H60.9300C20—C211.514 (2)
C7—C81.352 (3)C20—H20A0.9700
C7—H70.9300C20—H20B0.9700
C8—C8A1.429 (3)C21—C221.515 (3)
C8—H80.9300C21—H21A0.9700
C8A—C91.409 (3)C21—H21B0.9700
C8A—C10A1.432 (2)C22—C231.508 (3)
C9—C9A1.408 (2)C22—H22A0.9700
C9—C111.521 (2)C22—H22B0.9700
C10—C10A1.387 (3)C23—C241.516 (3)
C10—H100.9300C23—H23A0.9700
C11—H11A0.9700C23—H23B0.9700
C11—H11B0.9700C24—H24A0.9600
C13—C141.521 (3)C24—H24B0.9600
C13—H13A0.9700C24—H24C0.9600
C13—H13B0.9700
C11—N12—C13112.59 (16)H14A—C14—H14B107.9
C11—N12—H1299.2 (15)C16—C15—C14114.07 (16)
C13—N12—H12116.4 (16)C16—C15—H15A108.7
C2—C1—C9A121.89 (18)C14—C15—H15A108.7
C2—C1—H1119.1C16—C15—H15B108.7
C9A—C1—H1119.1C14—C15—H15B108.7
C1—C2—C3120.30 (19)H15A—C15—H15B107.6
C1—C2—H2119.8C15—C16—C17113.52 (15)
C3—C2—H2119.8C15—C16—H16A108.9
C4—C3—C2120.23 (19)C17—C16—H16A108.9
C4—C3—H3119.9C15—C16—H16B108.9
C2—C3—H3119.9C17—C16—H16B108.9
C3—C4—C4A121.47 (19)H16A—C16—H16B107.7
C3—C4—H4119.3C18—C17—C16114.04 (15)
C4A—C4—H4119.3C18—C17—H17A108.7
C10—C4A—C4121.90 (17)C16—C17—H17A108.7
C10—C4A—C9A119.33 (16)C18—C17—H17B108.7
C4—C4A—C9A118.75 (17)C16—C17—H17B108.7
C6—C5—C10A121.3 (2)H17A—C17—H17B107.6
C6—C5—H5119.4C19—C18—C17113.52 (16)
C10A—C5—H5119.4C19—C18—H18A108.9
C5—C6—C7119.9 (2)C17—C18—H18A108.9
C5—C6—H6120.0C19—C18—H18B108.9
C7—C6—H6120.0C17—C18—H18B108.9
C8—C7—C6121.1 (2)H18A—C18—H18B107.7
C8—C7—H7119.4C20—C19—C18114.51 (16)
C6—C7—H7119.4C20—C19—H19A108.6
C7—C8—C8A121.6 (2)C18—C19—H19A108.6
C7—C8—H8119.2C20—C19—H19B108.6
C8A—C8—H8119.2C18—C19—H19B108.6
C9—C8A—C8123.59 (17)H19A—C19—H19B107.6
C9—C8A—C10A119.48 (16)C21—C20—C19113.79 (16)
C8—C8A—C10A116.93 (17)C21—C20—H20A108.8
C9A—C9—C8A120.10 (15)C19—C20—H20A108.8
C9A—C9—C11119.25 (16)C21—C20—H20B108.8
C8A—C9—C11120.64 (16)C19—C20—H20B108.8
C9—C9A—C1123.09 (16)H20A—C20—H20B107.7
C9—C9A—C4A119.58 (16)C20—C21—C22114.98 (16)
C1—C9A—C4A117.32 (16)C20—C21—H21A108.5
C10A—C10—C4A121.73 (16)C22—C21—H21A108.5
C10A—C10—H10119.1C20—C21—H21B108.5
C4A—C10—H10119.1C22—C21—H21B108.5
C10—C10A—C5121.31 (17)H21A—C21—H21B107.5
C10—C10A—C8A119.57 (17)C23—C22—C21113.55 (17)
C5—C10A—C8A119.12 (18)C23—C22—H22A108.9
N12—C11—C9111.44 (14)C21—C22—H22A108.9
N12—C11—H11A109.3C23—C22—H22B108.9
C9—C11—H11A109.3C21—C22—H22B108.9
N12—C11—H11B109.3H22A—C22—H22B107.7
C9—C11—H11B109.3C22—C23—C24114.1 (2)
H11A—C11—H11B108.0C22—C23—H23A108.7
N12—C13—C14116.86 (16)C24—C23—H23A108.7
N12—C13—H13A108.1C22—C23—H23B108.7
C14—C13—H13A108.1C24—C23—H23B108.7
N12—C13—H13B108.1H23A—C23—H23B107.6
C14—C13—H13B108.1C23—C24—H24A109.5
H13A—C13—H13B107.3C23—C24—H24B109.5
C15—C14—C13111.89 (15)H24A—C24—H24B109.5
C15—C14—H14A109.2C23—C24—H24C109.5
C13—C14—H14A109.2H24A—C24—H24C109.5
C15—C14—H14B109.2H24B—C24—H24C109.5
C13—C14—H14B109.2
C9A—C1—C2—C30.9 (3)C4—C4A—C10—C10A177.14 (17)
C1—C2—C3—C40.4 (3)C9A—C4A—C10—C10A1.4 (3)
C2—C3—C4—C4A1.2 (3)C4A—C10—C10A—C5178.43 (17)
C3—C4—C4A—C10176.1 (2)C4A—C10—C10A—C8A1.6 (3)
C3—C4—C4A—C9A2.4 (3)C6—C5—C10A—C10179.71 (18)
C10A—C5—C6—C71.1 (3)C6—C5—C10A—C8A0.3 (3)
C5—C6—C7—C81.2 (3)C9—C8A—C10A—C101.6 (3)
C6—C7—C8—C8A0.1 (3)C8—C8A—C10A—C10178.41 (16)
C7—C8—C8A—C9178.48 (19)C9—C8A—C10A—C5178.41 (16)
C7—C8—C8A—C10A1.5 (3)C8—C8A—C10A—C51.6 (2)
C8—C8A—C9—C9A175.05 (16)C13—N12—C11—C9178.79 (16)
C10A—C8A—C9—C9A4.9 (3)C9A—C9—C11—N1279.3 (2)
C8—C8A—C9—C115.7 (3)C8A—C9—C11—N12101.5 (2)
C10A—C8A—C9—C11174.30 (15)C11—N12—C13—C1468.2 (2)
C8A—C9—C9A—C1173.44 (17)N12—C13—C14—C15174.07 (17)
C11—C9—C9A—C17.3 (3)C13—C14—C15—C16173.95 (17)
C8A—C9—C9A—C4A5.2 (3)C14—C15—C16—C17174.07 (17)
C11—C9—C9A—C4A174.08 (15)C15—C16—C17—C18178.00 (16)
C2—C1—C9A—C9178.93 (18)C16—C17—C18—C19178.94 (17)
C2—C1—C9A—C4A0.3 (3)C17—C18—C19—C20178.23 (17)
C10—C4A—C9A—C92.0 (2)C18—C19—C20—C21178.56 (17)
C4—C4A—C9A—C9179.42 (16)C19—C20—C21—C22178.01 (17)
C10—C4A—C9A—C1176.65 (17)C20—C21—C22—C23176.08 (18)
C4—C4A—C9A—C11.9 (2)C21—C22—C23—C24179.79 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg(1)i0.933.353.984 (3)127
C4—H4···Cg(2)i0.932.633.518 (3)161
C10—H10···Cg(3)i0.932.933.806 (2)158
C14—H14B···Cg(1)ii0.973.123.860 (2)135
C23—H23A···Cg(3)iii0.973.033.798 (3)137
C24—H24A···Cg(2)iii0.962.993.877 (3)155
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y, z1; (iii) x, y, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds