organic compounds
Tris[2-(pyrrol-2-ylmethyleneamino)ethyl]amine
aBeijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, People's Republic of China
*Correspondence e-mail: jnyao@iccas.ac.cn
The title compound, C21H27N7, was synthesized by reaction of tris(2-aminoethyl)amine and pyrrole-2-carbaldehyde in ethanol at room temperature. The structure is stabilized by intra- and intermolecular C—H⋯N and N—H⋯N hydrogen-bonding interactions.
Related literature
For the self-assembly of pyrrole Schiff base–metal complexes, see: Wu et al. (2003, 2006); Yang, Chen et al. (2004); Yang, Shan et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 2001); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536807065907/rz2179sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536807065907/rz2179Isup2.hkl
The title compound was prepared by reaction of tris(2-aminoethyl)amine, (0.05 mol) and pyrrole-2-carbaldehyde (0.15 mol) in ethanol (40 ml) at room temperature. Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/acetonitrile solution (1:1 v/v) at room temperature.
All H atoms were fixed geometrically and were treated as riding on the parent atoms, with C—H = 0.93–0.97 Å, N—H = 0.86 Å and with Uiso(H) = 1.2 Ueq(C, N).
Data collection: RAPID-AUTO (Rigaku, 2001); cell
RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C21H27N7 | F(000) = 808 |
Mr = 377.50 | Dx = 1.182 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 19300 reflections |
a = 11.494 (2) Å | θ = 1.9–27.5° |
b = 9.4875 (19) Å | µ = 0.08 mm−1 |
c = 20.232 (4) Å | T = 293 K |
β = 105.97 (3)° | Needle, brown |
V = 2121.1 (8) Å3 | 0.80 × 0.08 × 0.05 mm |
Z = 4 |
Rigaku R-AXIS RAPID IP diffractometer | 4832 independent reflections |
Radiation source: Rotating Anode | 1905 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
oscillation scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.943, Tmax = 0.995 | k = 0→12 |
19300 measured reflections | l = −13→26 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3 |
4832 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C21H27N7 | V = 2121.1 (8) Å3 |
Mr = 377.50 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.494 (2) Å | µ = 0.08 mm−1 |
b = 9.4875 (19) Å | T = 293 K |
c = 20.232 (4) Å | 0.80 × 0.08 × 0.05 mm |
β = 105.97 (3)° |
Rigaku R-AXIS RAPID IP diffractometer | 4832 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1905 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.995 | Rint = 0.069 |
19300 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.20 e Å−3 |
4832 reflections | Δρmin = −0.19 e Å−3 |
253 parameters |
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 | ||
N1 | 0.32208 (19) | 0.2117 (2) | −0.04712 (11) | 0.0456 (6) | |
N2 | 0.3346 (2) | 0.3634 (2) | −0.17842 (11) | 0.0439 (6) | |
N3 | 0.47309 (19) | 0.6138 (3) | −0.18248 (11) | 0.0493 (7) | |
H3A | 0.4361 | 0.6213 | −0.1510 | 0.059* | |
N4 | 0.1461 (2) | 0.1199 (3) | 0.03356 (12) | 0.0477 (6) | |
N5 | 0.1051 (2) | −0.1779 (3) | 0.05915 (12) | 0.0523 (7) | |
H5A | 0.0388 | −0.1426 | 0.0339 | 0.063* | |
N6 | 0.6284 (2) | 0.2840 (2) | 0.07191 (11) | 0.0443 (6) | |
N7 | 0.8400 (2) | 0.4282 (2) | 0.15596 (12) | 0.0453 (6) | |
H7A | 0.7761 | 0.4688 | 0.1611 | 0.054* | |
C1 | 0.3214 (3) | 0.1456 (3) | −0.11191 (15) | 0.0520 (8) | |
H1A | 0.2744 | 0.0595 | −0.1159 | 0.062* | |
H1B | 0.4039 | 0.1183 | −0.1093 | 0.062* | |
C2 | 0.2728 (3) | 0.2291 (3) | −0.17799 (14) | 0.0503 (8) | |
H2B | 0.2810 | 0.1726 | −0.2164 | 0.060* | |
H2C | 0.1873 | 0.2469 | −0.1845 | 0.060* | |
C3 | 0.4025 (3) | 0.3753 (3) | −0.21867 (14) | 0.0470 (8) | |
H3B | 0.4080 | 0.2990 | −0.2465 | 0.056* | |
C4 | 0.4703 (3) | 0.4995 (3) | −0.22330 (15) | 0.0454 (7) | |
C5 | 0.5409 (3) | 0.5307 (4) | −0.26616 (17) | 0.0646 (10) | |
H5B | 0.5556 | 0.4714 | −0.2996 | 0.078* | |
C6 | 0.5863 (3) | 0.6656 (4) | −0.25109 (18) | 0.0690 (10) | |
H6B | 0.6366 | 0.7136 | −0.2725 | 0.083* | |
C7 | 0.5439 (3) | 0.7142 (4) | −0.19947 (16) | 0.0620 (9) | |
H7B | 0.5604 | 0.8023 | −0.1789 | 0.074* | |
C8 | 0.2084 (2) | 0.2788 (3) | −0.04489 (15) | 0.0553 (8) | |
H8A | 0.1423 | 0.2371 | −0.0799 | 0.066* | |
H8B | 0.2117 | 0.3782 | −0.0555 | 0.066* | |
C9 | 0.1833 (3) | 0.2634 (3) | 0.02435 (15) | 0.0536 (8) | |
H9A | 0.2556 | 0.2865 | 0.0606 | 0.064* | |
H9B | 0.1199 | 0.3285 | 0.0274 | 0.064* | |
C10 | 0.2245 (3) | 0.0402 (4) | 0.07166 (15) | 0.0513 (8) | |
H10A | 0.2993 | 0.0804 | 0.0929 | 0.062* | |
C11 | 0.2099 (3) | −0.1055 (3) | 0.08539 (15) | 0.0483 (8) | |
C12 | 0.2924 (3) | −0.2002 (4) | 0.12203 (16) | 0.0643 (10) | |
H12A | 0.3723 | −0.1802 | 0.1455 | 0.077* | |
C13 | 0.2371 (3) | −0.3313 (4) | 0.11832 (18) | 0.0688 (10) | |
H13A | 0.2724 | −0.4144 | 0.1388 | 0.083* | |
C14 | 0.1217 (3) | −0.3143 (4) | 0.07898 (17) | 0.0640 (9) | |
H14A | 0.0634 | −0.3849 | 0.0675 | 0.077* | |
C15 | 0.4299 (2) | 0.2945 (3) | −0.01526 (14) | 0.0475 (8) | |
H15A | 0.4098 | 0.3670 | 0.0135 | 0.057* | |
H15B | 0.4583 | 0.3405 | −0.0507 | 0.057* | |
C16 | 0.5290 (2) | 0.2023 (3) | 0.02762 (15) | 0.0508 (8) | |
H16A | 0.4952 | 0.1410 | 0.0560 | 0.061* | |
H16B | 0.5606 | 0.1433 | −0.0026 | 0.061* | |
C17 | 0.7349 (3) | 0.2535 (3) | 0.07048 (14) | 0.0448 (7) | |
H17A | 0.7445 | 0.1841 | 0.0399 | 0.054* | |
C18 | 0.8415 (2) | 0.3190 (3) | 0.11291 (13) | 0.0422 (7) | |
C19 | 0.9607 (3) | 0.2851 (4) | 0.12042 (15) | 0.0558 (9) | |
H19A | 0.9887 | 0.2142 | 0.0970 | 0.067* | |
C20 | 1.0321 (3) | 0.3751 (4) | 0.16917 (17) | 0.0640 (10) | |
H20A | 1.1161 | 0.3751 | 0.1848 | 0.077* | |
C21 | 0.9557 (3) | 0.4631 (4) | 0.18960 (16) | 0.0587 (9) | |
H21A | 0.9787 | 0.5355 | 0.2215 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0367 (14) | 0.0511 (15) | 0.0462 (14) | −0.0059 (12) | 0.0069 (11) | 0.0022 (14) |
N2 | 0.0470 (15) | 0.0457 (15) | 0.0387 (14) | −0.0016 (13) | 0.0110 (11) | −0.0027 (13) |
N3 | 0.0465 (15) | 0.0601 (17) | 0.0389 (14) | −0.0048 (14) | 0.0076 (12) | 0.0047 (15) |
N4 | 0.0402 (14) | 0.0572 (17) | 0.0477 (15) | −0.0037 (13) | 0.0154 (12) | 0.0050 (14) |
N5 | 0.0446 (16) | 0.0555 (17) | 0.0549 (16) | 0.0010 (13) | 0.0104 (12) | 0.0092 (15) |
N6 | 0.0392 (15) | 0.0470 (14) | 0.0438 (14) | −0.0015 (12) | 0.0066 (11) | −0.0065 (13) |
N7 | 0.0389 (14) | 0.0478 (15) | 0.0489 (15) | −0.0009 (12) | 0.0118 (11) | 0.0055 (14) |
C1 | 0.0474 (18) | 0.0435 (18) | 0.061 (2) | −0.0076 (16) | 0.0084 (15) | 0.0023 (18) |
C2 | 0.0528 (19) | 0.0506 (19) | 0.0442 (18) | −0.0093 (16) | 0.0080 (15) | −0.0090 (17) |
C3 | 0.0523 (19) | 0.0499 (19) | 0.0377 (16) | 0.0076 (17) | 0.0103 (15) | −0.0031 (16) |
C4 | 0.0474 (18) | 0.0479 (19) | 0.0404 (17) | 0.0032 (16) | 0.0110 (14) | 0.0010 (17) |
C5 | 0.066 (2) | 0.076 (3) | 0.060 (2) | 0.006 (2) | 0.0314 (18) | 0.007 (2) |
C6 | 0.063 (2) | 0.086 (3) | 0.061 (2) | −0.011 (2) | 0.0206 (18) | 0.018 (2) |
C7 | 0.062 (2) | 0.060 (2) | 0.055 (2) | −0.0187 (19) | 0.0002 (17) | 0.010 (2) |
C8 | 0.0402 (18) | 0.067 (2) | 0.0571 (19) | −0.0017 (17) | 0.0110 (15) | 0.0140 (19) |
C9 | 0.0436 (18) | 0.064 (2) | 0.0541 (19) | −0.0028 (17) | 0.0150 (15) | 0.0061 (18) |
C10 | 0.0402 (18) | 0.072 (2) | 0.0429 (18) | −0.0119 (18) | 0.0141 (14) | −0.0050 (19) |
C11 | 0.0395 (18) | 0.062 (2) | 0.0438 (18) | −0.0033 (17) | 0.0114 (14) | 0.0017 (18) |
C12 | 0.0400 (19) | 0.088 (3) | 0.059 (2) | 0.004 (2) | 0.0024 (16) | 0.012 (2) |
C13 | 0.063 (2) | 0.067 (2) | 0.074 (2) | 0.014 (2) | 0.0140 (19) | 0.018 (2) |
C14 | 0.058 (2) | 0.062 (2) | 0.070 (2) | −0.0003 (19) | 0.0128 (19) | 0.009 (2) |
C15 | 0.0443 (18) | 0.0481 (18) | 0.0476 (17) | −0.0060 (15) | 0.0087 (14) | 0.0018 (16) |
C16 | 0.0450 (18) | 0.0510 (19) | 0.0530 (18) | −0.0034 (16) | 0.0077 (14) | −0.0060 (17) |
C17 | 0.0464 (19) | 0.0486 (18) | 0.0404 (16) | 0.0026 (16) | 0.0134 (14) | −0.0026 (16) |
C18 | 0.0435 (19) | 0.0478 (19) | 0.0370 (16) | −0.0018 (15) | 0.0141 (14) | 0.0012 (16) |
C19 | 0.0418 (19) | 0.075 (2) | 0.056 (2) | 0.0056 (18) | 0.0231 (15) | 0.007 (2) |
C20 | 0.0361 (18) | 0.080 (3) | 0.073 (2) | −0.004 (2) | 0.0112 (17) | 0.013 (2) |
C21 | 0.047 (2) | 0.058 (2) | 0.061 (2) | −0.0204 (18) | −0.0026 (16) | 0.0047 (19) |
N1—C1 | 1.451 (3) | C6—H6B | 0.9300 |
N1—C15 | 1.460 (3) | C7—H7B | 0.9300 |
N1—C8 | 1.465 (3) | C8—C9 | 1.513 (4) |
N2—C3 | 1.279 (3) | C8—H8A | 0.9700 |
N2—C2 | 1.459 (3) | C8—H8B | 0.9700 |
N3—C7 | 1.357 (4) | C9—H9A | 0.9700 |
N3—C4 | 1.358 (3) | C9—H9B | 0.9700 |
N3—H3A | 0.8600 | C10—C11 | 1.429 (4) |
N4—C10 | 1.264 (3) | C10—H10A | 0.9300 |
N4—C9 | 1.454 (4) | C11—C12 | 1.368 (4) |
N5—C14 | 1.352 (4) | C12—C13 | 1.388 (4) |
N5—C11 | 1.362 (3) | C12—H12A | 0.9300 |
N5—H5A | 0.8600 | C13—C14 | 1.356 (4) |
N6—C17 | 1.267 (3) | C13—H13A | 0.9300 |
N6—C16 | 1.464 (3) | C14—H14A | 0.9300 |
N7—C21 | 1.357 (3) | C15—C16 | 1.506 (3) |
N7—C18 | 1.357 (3) | C15—H15A | 0.9700 |
N7—H7A | 0.8600 | C15—H15B | 0.9700 |
C1—C2 | 1.522 (4) | C16—H16A | 0.9700 |
C1—H1A | 0.9700 | C16—H16B | 0.9700 |
C1—H1B | 0.9700 | C17—C18 | 1.430 (4) |
C2—H2B | 0.9700 | C17—H17A | 0.9300 |
C2—H2C | 0.9700 | C18—C19 | 1.374 (4) |
C3—C4 | 1.430 (4) | C19—C20 | 1.389 (4) |
C3—H3B | 0.9300 | C19—H19A | 0.9300 |
C4—C5 | 1.373 (4) | C20—C21 | 1.356 (4) |
C5—C6 | 1.385 (4) | C20—H20A | 0.9300 |
C5—H5B | 0.9300 | C21—H21A | 0.9300 |
C6—C7 | 1.350 (4) | ||
C1—N1—C15 | 115.1 (2) | N4—C9—C8 | 110.3 (3) |
C1—N1—C8 | 115.6 (2) | N4—C9—H9A | 109.6 |
C15—N1—C8 | 114.1 (2) | C8—C9—H9A | 109.6 |
C3—N2—C2 | 117.7 (2) | N4—C9—H9B | 109.6 |
C7—N3—C4 | 108.8 (3) | C8—C9—H9B | 109.6 |
C7—N3—H3A | 125.6 | H9A—C9—H9B | 108.1 |
C4—N3—H3A | 125.6 | N4—C10—C11 | 126.5 (3) |
C10—N4—C9 | 117.0 (3) | N4—C10—H10A | 116.7 |
C14—N5—C11 | 109.3 (3) | C11—C10—H10A | 116.7 |
C14—N5—H5A | 125.4 | N5—C11—C12 | 106.6 (3) |
C11—N5—H5A | 125.4 | N5—C11—C10 | 123.5 (3) |
C17—N6—C16 | 117.5 (2) | C12—C11—C10 | 129.8 (3) |
C21—N7—C18 | 108.9 (3) | C11—C12—C13 | 108.7 (3) |
C21—N7—H7A | 125.5 | C11—C12—H12A | 125.6 |
C18—N7—H7A | 125.5 | C13—C12—H12A | 125.6 |
N1—C1—C2 | 118.6 (2) | C14—C13—C12 | 106.5 (3) |
N1—C1—H1A | 107.7 | C14—C13—H13A | 126.7 |
C2—C1—H1A | 107.7 | C12—C13—H13A | 126.7 |
N1—C1—H1B | 107.7 | N5—C14—C13 | 108.8 (3) |
C2—C1—H1B | 107.7 | N5—C14—H14A | 125.6 |
H1A—C1—H1B | 107.1 | C13—C14—H14A | 125.6 |
N2—C2—C1 | 113.5 (2) | N1—C15—C16 | 110.9 (2) |
N2—C2—H2B | 108.9 | N1—C15—H15A | 109.5 |
C1—C2—H2B | 108.9 | C16—C15—H15A | 109.5 |
N2—C2—H2C | 108.9 | N1—C15—H15B | 109.5 |
C1—C2—H2C | 108.9 | C16—C15—H15B | 109.5 |
H2B—C2—H2C | 107.7 | H15A—C15—H15B | 108.0 |
N2—C3—C4 | 123.7 (3) | N6—C16—C15 | 112.6 (2) |
N2—C3—H3B | 118.2 | N6—C16—H16A | 109.1 |
C4—C3—H3B | 118.2 | C15—C16—H16A | 109.1 |
N3—C4—C5 | 107.0 (3) | N6—C16—H16B | 109.1 |
N3—C4—C3 | 122.7 (3) | C15—C16—H16B | 109.1 |
C5—C4—C3 | 130.3 (3) | H16A—C16—H16B | 107.8 |
C4—C5—C6 | 108.2 (3) | N6—C17—C18 | 124.1 (3) |
C4—C5—H5B | 125.9 | N6—C17—H17A | 117.9 |
C6—C5—H5B | 125.9 | C18—C17—H17A | 117.9 |
C7—C6—C5 | 106.9 (3) | N7—C18—C19 | 107.2 (3) |
C7—C6—H6B | 126.5 | N7—C18—C17 | 123.8 (3) |
C5—C6—H6B | 126.5 | C19—C18—C17 | 128.9 (3) |
C6—C7—N3 | 109.0 (3) | C18—C19—C20 | 108.1 (3) |
C6—C7—H7B | 125.5 | C18—C19—H19A | 125.9 |
N3—C7—H7B | 125.5 | C20—C19—H19A | 125.9 |
N1—C8—C9 | 112.7 (2) | C21—C20—C19 | 106.8 (3) |
N1—C8—H8A | 109.1 | C21—C20—H20A | 126.6 |
C9—C8—H8A | 109.1 | C19—C20—H20A | 126.6 |
N1—C8—H8B | 109.1 | C20—C21—N7 | 108.9 (3) |
C9—C8—H8B | 109.1 | C20—C21—H21A | 125.5 |
H8A—C8—H8B | 107.8 | N7—C21—H21A | 125.5 |
C15—N1—C1—C2 | −87.6 (3) | N4—C10—C11—N5 | −1.3 (5) |
C8—N1—C1—C2 | 48.9 (3) | N4—C10—C11—C12 | 175.1 (3) |
C3—N2—C2—C1 | 110.2 (3) | N5—C11—C12—C13 | −0.3 (4) |
N1—C1—C2—N2 | 56.6 (3) | C10—C11—C12—C13 | −177.2 (3) |
C2—N2—C3—C4 | −178.6 (3) | C11—C12—C13—C14 | 0.4 (4) |
C7—N3—C4—C5 | 0.0 (3) | C11—N5—C14—C13 | 0.1 (4) |
C7—N3—C4—C3 | −179.5 (2) | C12—C13—C14—N5 | −0.3 (4) |
N2—C3—C4—N3 | 3.4 (4) | C1—N1—C15—C16 | −85.5 (3) |
N2—C3—C4—C5 | −175.9 (3) | C8—N1—C15—C16 | 137.4 (2) |
N3—C4—C5—C6 | −0.2 (4) | C17—N6—C16—C15 | −129.8 (3) |
C3—C4—C5—C6 | 179.2 (3) | N1—C15—C16—N6 | −167.7 (2) |
C4—C5—C6—C7 | 0.3 (4) | C16—N6—C17—C18 | −177.0 (3) |
C5—C6—C7—N3 | −0.3 (4) | C21—N7—C18—C19 | 0.4 (3) |
C4—N3—C7—C6 | 0.2 (3) | C21—N7—C18—C17 | 178.7 (3) |
C1—N1—C8—C9 | 144.0 (3) | N6—C17—C18—N7 | −4.9 (4) |
C15—N1—C8—C9 | −79.1 (3) | N6—C17—C18—C19 | 173.0 (3) |
C10—N4—C9—C8 | 102.4 (3) | N7—C18—C19—C20 | 0.3 (3) |
N1—C8—C9—N4 | −73.9 (3) | C17—C18—C19—C20 | −177.9 (3) |
C9—N4—C10—C11 | −177.0 (3) | C18—C19—C20—C21 | −0.9 (4) |
C14—N5—C11—C12 | 0.1 (3) | C19—C20—C21—N7 | 1.1 (4) |
C14—N5—C11—C10 | 177.3 (3) | C18—N7—C21—C20 | −0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···N2 | 0.97 | 2.59 | 3.246 (4) | 125 |
N3—H3A···N6i | 0.86 | 2.14 | 2.956 (3) | 159 |
N5—H5A···N4ii | 0.86 | 2.20 | 3.029 (3) | 163 |
N7—H7A···N2i | 0.86 | 2.13 | 2.940 (3) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H27N7 |
Mr | 377.50 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.494 (2), 9.4875 (19), 20.232 (4) |
β (°) | 105.97 (3) |
V (Å3) | 2121.1 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.80 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.943, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19300, 4832, 1905 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.142, 1.01 |
No. of reflections | 4832 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1994).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···N2 | 0.97 | 2.59 | 3.246 (4) | 124.8 |
N3—H3A···N6i | 0.86 | 2.14 | 2.956 (3) | 158.8 |
N5—H5A···N4ii | 0.86 | 2.20 | 3.029 (3) | 162.6 |
N7—H7A···N2i | 0.86 | 2.13 | 2.940 (3) | 157.5 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (grant Nos. 90301010, 50573084, 90606004).
References
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1994). SHELXTL/PC. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
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The chemistry and crystal structure of Schiff base derivatives of pyrrole have been extensively studied for many years as these compounds represent the basic units of porphyrins. More recently, it has been pointed out that pyrrole Schiff bases are ideal building blocks for the self-assembly of metallosupramolecules (Wu et al., 2006; Wu et al., 2003; Yang, Chen et al., 2004; Yang, Shan et al., 2004) due to the presence of many hydrogen bond donors and acceptors. In view of its potential interest in this field, the title compound was synthesized and its crystal structure is reported here.
In the title compound, bond lengths and angles are as expected, with the N2—C3, N4—C10 and N6—C17 bond lengths (mean value 1.270 (3) Å) indicating a remarkable double-bond character. The molecular conformation is stabilized by an intramolecular C—H···N hydrogen bond (Table 1). In the crystal structure, the molecules are linked by intermolecular N—H···N hydrogen bonding interactions (Table 1).