Tris[2-(pyrrol-2-ylmethyl-eneamino)eth-yl]amine.

The title compound, C(21)H(27)N(7), was synthesized by reaction of tris-(2-amino-ethyl)amine and pyrrole-2-carbaldehyde in ethanol at room temperature. The structure is stabilized by intra- and inter-molecular C-H⋯N and N-H⋯N hydrogen-bonding inter-actions.

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

C21H27N7

M = 377.50

Monoclinic,

a = 11.494 (2) Å

b = 9.4875 (19) Å

c = 20.232 (4) Å

β = 105.97 (3)°

V = 2121.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.80 × 0.08 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.943, T max = 0.995

19300 measured reflections

4832 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.0685

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.01

4832 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065907/rz2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065907/rz2179Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H27N7	F000 = 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 = 1.9–27.5º
b = 9.4875 (19) Å	µ = 0.08 mm−1
c = 20.232 (4) Å	T = 293 (2) K
β = 105.97 (3)º	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)
Monochromator: graphite	Rint = 0.069
T = 293(2) K	θmax = 27.5º
oscillation scans	θmin = 1.9º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4832 reflections	Δρmax = 0.20 e Å−3
253 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .