1,4,N-Tri-tert-butyl-2,5-bis-tert-butyl­imino-1,2,4,5-tetra­hydro­pyrrolo[3,2-b]pyrrol-3-amine

The title compound, C₂₆H₄₇N₅, is the first unsymmetrically substituted tetra­hydro­pyrrolo[3,2-b]pyrrole derivative to be structurally characterized. The bicyclic ring system with two exocyclic imine functions and one amino group is formed by the oligomerization of five tert-butyl ­isocyanide groups.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• R factor = 0.057
• wR factor = 0.137
• Data-to-parameter ratio = 20.5

checkCIF/PLATON results

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Datablock: I

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: XP (Siemens, 1990).

1,4,N-Tri-tert-butyl-2,5-bis-tert-butylimino-1,2,4,5- tetrahydropyrrolo[3,2-b]pyrrol-3-amine

Crystal data

C26H47N5	F(000) = 952
Mr = 429.69	Dx = 1.064 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3452 reflections
a = 11.5558 (4) Å	θ = 2.6–27.5°
b = 17.9911 (9) Å	µ = 0.06 mm^−1
c = 12.9268 (6) Å	T = 183 K
β = 93.201 (3)°	Prism, colourless
V = 2683.3 (2) Å^3	0.04 × 0.04 × 0.04 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3452 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
φ an ω scans	h = −14→15
17978 measured reflections	k = −23→22
6112 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.3727P] where P = (Fo^2 + 2Fc^2)/3
6112 reflections	(Δ/σ)max = 0.003
298 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

Special details

Experimental. IR (KBr, 298 K) [cm^-1]: 3273 (m), 2967 (s), 2927 (s), 2868 (m), 1638 (s), 1591 (s), 1449 (m), 1388 (m), 1360 (s), 1260 (s), 1208 (s), 1185 (m); MS (DEI) [m/z (%)]: 429 (3, M⁺), 373 (2, MH⁺ - C₄H₉), 316 (4, MH⁺ - 2 C₄H₉), 260 (6, MH₂⁺ - 3 C₄H₉), 204 (5, MH₃⁺ - 4 C₄H₉), 148 (11 MH₄⁺ - 5 C₄H₉).

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
N2	0.27736 (11)	0.06768 (8)	0.20082 (11)	0.0236 (4)
N1	0.12011 (11)	−0.01261 (8)	0.17137 (11)	0.0258 (4)
N5	0.52851 (11)	−0.02594 (8)	0.29680 (11)	0.0225 (3)
N4	0.68003 (12)	0.05591 (9)	0.33964 (11)	0.0287 (4)
N3	0.52880 (13)	0.15913 (8)	0.17758 (12)	0.0259 (4)
H31	0.5865 (11)	0.1803 (10)	0.2061 (13)	0.031*
C4	0.58173 (14)	0.04643 (10)	0.29281 (13)	0.0227 (4)
C5	0.41306 (14)	−0.01727 (10)	0.26645 (12)	0.0210 (4)
C2	0.39326 (13)	0.05947 (10)	0.23374 (13)	0.0204 (4)
C3	0.49630 (14)	0.09544 (9)	0.23354 (13)	0.0213 (4)
C1	0.22489 (14)	−0.00512 (10)	0.20483 (13)	0.0234 (4)
C7	0.05480 (14)	−0.08305 (10)	0.16988 (14)	0.0258 (4)
C11	0.20459 (15)	0.13493 (10)	0.22253 (15)	0.0300 (5)
C6	0.31381 (13)	−0.05622 (10)	0.24809 (13)	0.0235 (4)
H6	0.3038	−0.1066	0.2607	0.028*
C23	0.58424 (14)	−0.09205 (10)	0.34880 (14)	0.0249 (4)
C10	0.10545 (15)	−0.13795 (11)	0.09385 (15)	0.0322 (5)
H10A	0.1091	−0.1148	0.0272	0.048*
H10B	0.0570	−0.1812	0.0878	0.048*
H10C	0.1820	−0.1522	0.1189	0.048*
C19	0.74318 (15)	0.12594 (12)	0.36293 (15)	0.0337 (5)
C26	0.70172 (15)	−0.10632 (12)	0.30347 (17)	0.0397 (5)
H26A	0.6916	−0.1106	0.2295	0.060*
H26B	0.7342	−0.1516	0.3317	0.060*
H26C	0.7531	−0.0657	0.3208	0.060*
C15	0.54563 (16)	0.14709 (11)	0.06436 (14)	0.0317 (5)
C22	0.81251 (16)	0.15123 (12)	0.27222 (16)	0.0392 (5)
H22A	0.8578	0.1104	0.2488	0.059*
H22B	0.8631	0.1912	0.2942	0.059*
H22C	0.7603	0.1679	0.2166	0.059*
C25	0.50896 (15)	−0.16037 (10)	0.32688 (16)	0.0319 (5)
H25A	0.4368	−0.1547	0.3594	0.048*
H25B	0.5484	−0.2037	0.3540	0.048*
H25C	0.4942	−0.1658	0.2534	0.048*
C9	0.04860 (16)	−0.11709 (12)	0.27787 (15)	0.0361 (5)
H9A	0.1243	−0.1336	0.3021	0.054*
H9B	−0.0037	−0.1586	0.2747	0.054*
H9C	0.0212	−0.0804	0.3246	0.054*
C8	−0.06773 (14)	−0.06227 (11)	0.12907 (16)	0.0333 (5)
H8A	−0.1006	−0.0277	0.1757	0.050*
H8B	−0.1149	−0.1062	0.1240	0.050*
H8C	−0.0646	−0.0399	0.0619	0.050*
C14	0.12294 (18)	0.15125 (12)	0.12845 (18)	0.0431 (6)
H14A	0.1674	0.1589	0.0688	0.065*
H14B	0.0787	0.1951	0.1412	0.065*
H14C	0.0714	0.1100	0.1162	0.065*
C24	0.59750 (17)	−0.08007 (12)	0.46540 (15)	0.0383 (5)
H24A	0.6476	−0.0384	0.4801	0.057*
H24B	0.6305	−0.1238	0.4979	0.057*
H24C	0.5229	−0.0705	0.4917	0.057*
C18	0.61862 (18)	0.07777 (11)	0.04708 (16)	0.0419 (5)
H18A	0.6922	0.0825	0.0848	0.063*
H18B	0.6306	0.0725	−0.0255	0.063*
H18C	0.5789	0.0347	0.0710	0.063*
C21	0.66613 (18)	0.18824 (13)	0.40045 (17)	0.0460 (6)
H21A	0.6102	0.2017	0.3460	0.069*
H21B	0.7130	0.2307	0.4193	0.069*
H21C	0.6267	0.1715	0.4596	0.069*
C20	0.82989 (19)	0.10426 (15)	0.45208 (18)	0.0604 (7)
H20A	0.7885	0.0879	0.5103	0.091*
H20B	0.8768	0.1465	0.4718	0.091*
H20C	0.8786	0.0648	0.4299	0.091*
C13	0.28154 (16)	0.20216 (11)	0.24417 (19)	0.0434 (6)
H13A	0.3330	0.1925	0.3035	0.065*
H13B	0.2343	0.2446	0.2575	0.065*
H13C	0.3260	0.2119	0.1851	0.065*
C12	0.13658 (17)	0.12059 (13)	0.31861 (17)	0.0446 (6)
H12A	0.0834	0.0803	0.3052	0.067*
H12B	0.0943	0.1646	0.3352	0.067*
H12C	0.1894	0.1079	0.3759	0.067*
C17	0.60712 (19)	0.21663 (12)	0.02722 (16)	0.0454 (6)
H17A	0.5626	0.2599	0.0427	0.068*
H17B	0.6147	0.2136	−0.0462	0.068*
H17C	0.6826	0.2201	0.0618	0.068*
C16	0.42881 (18)	0.13947 (14)	0.00506 (16)	0.0474 (6)
H16A	0.3868	0.0987	0.0329	0.071*
H16B	0.4406	0.1303	−0.0668	0.071*
H16C	0.3853	0.1845	0.0116	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.0194 (7)	0.0190 (8)	0.0320 (9)	−0.0003 (6)	−0.0011 (6)	−0.0015 (7)
N1	0.0201 (8)	0.0257 (9)	0.0312 (9)	−0.0021 (6)	−0.0020 (6)	−0.0003 (7)
N5	0.0182 (7)	0.0214 (8)	0.0275 (8)	−0.0033 (6)	−0.0022 (6)	0.0056 (7)
N4	0.0227 (8)	0.0342 (10)	0.0288 (9)	−0.0073 (7)	−0.0024 (7)	0.0045 (7)
N3	0.0303 (8)	0.0208 (9)	0.0265 (9)	−0.0073 (7)	−0.0005 (7)	0.0003 (7)
C4	0.0220 (9)	0.0239 (10)	0.0224 (9)	−0.0041 (8)	0.0027 (7)	0.0022 (8)
C5	0.0224 (9)	0.0241 (10)	0.0163 (9)	−0.0007 (7)	0.0003 (7)	0.0008 (7)
C2	0.0210 (9)	0.0202 (10)	0.0199 (9)	0.0018 (7)	0.0011 (7)	−0.0016 (7)
C3	0.0224 (9)	0.0192 (10)	0.0223 (9)	−0.0017 (7)	0.0014 (7)	−0.0012 (7)
C1	0.0247 (9)	0.0212 (10)	0.0244 (10)	−0.0016 (8)	0.0031 (8)	−0.0004 (8)
C7	0.0225 (9)	0.0238 (10)	0.0310 (11)	−0.0049 (8)	−0.0003 (8)	0.0000 (8)
C11	0.0237 (9)	0.0245 (11)	0.0412 (12)	0.0060 (8)	−0.0042 (8)	−0.0074 (9)
C6	0.0226 (9)	0.0195 (10)	0.0284 (10)	−0.0022 (8)	0.0000 (7)	0.0031 (8)
C23	0.0215 (9)	0.0235 (10)	0.0294 (10)	0.0015 (8)	−0.0016 (8)	0.0069 (8)
C10	0.0300 (10)	0.0303 (12)	0.0358 (11)	−0.0034 (8)	−0.0038 (8)	−0.0016 (9)
C19	0.0276 (10)	0.0405 (13)	0.0322 (11)	−0.0147 (9)	−0.0039 (8)	0.0035 (9)
C26	0.0253 (10)	0.0363 (13)	0.0580 (14)	0.0069 (9)	0.0052 (9)	0.0047 (11)
C15	0.0422 (11)	0.0289 (11)	0.0242 (10)	−0.0032 (9)	0.0040 (8)	0.0042 (8)
C22	0.0288 (10)	0.0415 (13)	0.0476 (13)	−0.0102 (9)	0.0035 (9)	0.0037 (10)
C25	0.0293 (10)	0.0236 (11)	0.0424 (12)	0.0025 (8)	−0.0025 (9)	0.0051 (9)
C9	0.0335 (11)	0.0382 (13)	0.0365 (12)	−0.0088 (9)	0.0013 (9)	0.0040 (10)
C8	0.0214 (9)	0.0353 (12)	0.0428 (12)	−0.0031 (8)	−0.0013 (8)	−0.0017 (9)
C14	0.0433 (12)	0.0272 (12)	0.0566 (15)	0.0092 (9)	−0.0176 (11)	−0.0001 (10)
C24	0.0444 (12)	0.0372 (13)	0.0323 (12)	−0.0037 (10)	−0.0057 (9)	0.0117 (10)
C18	0.0590 (13)	0.0361 (13)	0.0320 (12)	−0.0028 (11)	0.0153 (10)	−0.0046 (10)
C21	0.0496 (13)	0.0473 (15)	0.0417 (13)	−0.0213 (11)	0.0078 (10)	−0.0155 (11)
C20	0.0519 (14)	0.0710 (19)	0.0553 (16)	−0.0315 (13)	−0.0246 (12)	0.0148 (13)
C13	0.0343 (11)	0.0233 (11)	0.0721 (16)	0.0058 (9)	−0.0028 (11)	−0.0168 (11)
C12	0.0296 (10)	0.0553 (15)	0.0491 (14)	0.0022 (10)	0.0036 (10)	−0.0205 (11)
C17	0.0605 (14)	0.0375 (13)	0.0391 (12)	−0.0081 (11)	0.0093 (10)	0.0130 (10)
C16	0.0567 (14)	0.0539 (16)	0.0306 (12)	−0.0081 (11)	−0.0070 (10)	0.0073 (11)

Geometric parameters (Å, º)

N2—C2	1.390 (2)	C22—H22A	0.9600
N2—C1	1.445 (2)	C22—H22B	0.9600
N2—C11	1.509 (2)	C22—H22C	0.9600
N1—C1	1.270 (2)	C25—H25A	0.9600
N1—C7	1.475 (2)	C25—H25B	0.9600
N5—C5	1.378 (2)	C25—H25C	0.9600
N5—C4	1.442 (2)	C9—H9A	0.9600
N5—C23	1.494 (2)	C9—H9B	0.9600
N4—C4	1.268 (2)	C9—H9C	0.9600
N4—C19	1.478 (2)	C8—H8A	0.9600
N3—C3	1.417 (2)	C8—H8B	0.9600
N3—C15	1.503 (2)	C8—H8C	0.9600
N3—H31	0.835 (9)	C14—H14A	0.9600
C4—C3	1.502 (2)	C14—H14B	0.9600
C5—C6	1.354 (2)	C14—H14C	0.9600
C5—C2	1.458 (2)	C24—H24A	0.9600
C2—C3	1.355 (2)	C24—H24B	0.9600
C1—C6	1.466 (2)	C24—H24C	0.9600
C7—C8	1.529 (2)	C18—H18A	0.9600
C7—C9	1.530 (3)	C18—H18B	0.9600
C7—C10	1.533 (3)	C18—H18C	0.9600
C11—C13	1.518 (3)	C21—H21A	0.9600
C11—C14	1.526 (3)	C21—H21B	0.9600
C11—C12	1.528 (3)	C21—H21C	0.9600
C6—H6	0.9300	C20—H20A	0.9600
C23—C24	1.522 (3)	C20—H20B	0.9600
C23—C25	1.523 (2)	C20—H20C	0.9600
C23—C26	1.530 (2)	C13—H13A	0.9600
C10—H10A	0.9600	C13—H13B	0.9600
C10—H10B	0.9600	C13—H13C	0.9600
C10—H10C	0.9600	C12—H12A	0.9600
C19—C22	1.526 (3)	C12—H12B	0.9600
C19—C21	1.527 (3)	C12—H12C	0.9600
C19—C20	1.535 (3)	C17—H17A	0.9600
C26—H26A	0.9600	C17—H17B	0.9600
C26—H26B	0.9600	C17—H17C	0.9600
C26—H26C	0.9600	C16—H16A	0.9600
C15—C16	1.521 (3)	C16—H16B	0.9600
C15—C18	1.529 (3)	C16—H16C	0.9600
C15—C17	1.529 (3)
C2—N2—C1	106.96 (13)	H22A—C22—H22C	109.5
C2—N2—C11	124.45 (14)	H22B—C22—H22C	109.5
C1—N2—C11	118.73 (13)	C23—C25—H25A	109.5
C1—N1—C7	124.98 (15)	C23—C25—H25B	109.5
C5—N5—C4	107.19 (13)	H25A—C25—H25B	109.5
C5—N5—C23	127.17 (13)	C23—C25—H25C	109.5
C4—N5—C23	124.11 (13)	H25A—C25—H25C	109.5
C4—N4—C19	129.09 (16)	H25B—C25—H25C	109.5
C3—N3—C15	115.66 (14)	C7—C9—H9A	109.5
C3—N3—H31	111.8 (14)	C7—C9—H9B	109.5
C15—N3—H31	110.6 (13)	H9A—C9—H9B	109.5
N4—C4—N5	118.47 (16)	C7—C9—H9C	109.5
N4—C4—C3	135.25 (17)	H9A—C9—H9C	109.5
N5—C4—C3	106.20 (13)	H9B—C9—H9C	109.5
C6—C5—N5	142.05 (17)	C7—C8—H8A	109.5
C6—C5—C2	108.76 (15)	C7—C8—H8B	109.5
N5—C5—C2	108.87 (14)	H8A—C8—H8B	109.5
C3—C2—N2	141.27 (17)	C7—C8—H8C	109.5
C3—C2—C5	109.21 (14)	H8A—C8—H8C	109.5
N2—C2—C5	108.79 (14)	H8B—C8—H8C	109.5
C2—C3—N3	130.17 (16)	C11—C14—H14A	109.5
C2—C3—C4	105.74 (15)	C11—C14—H14B	109.5
N3—C3—C4	123.37 (14)	H14A—C14—H14B	109.5
N1—C1—N2	118.54 (15)	C11—C14—H14C	109.5
N1—C1—C6	134.26 (17)	H14A—C14—H14C	109.5
N2—C1—C6	107.19 (14)	H14B—C14—H14C	109.5
N1—C7—C8	104.94 (15)	C23—C24—H24A	109.5
N1—C7—C9	112.46 (15)	C23—C24—H24B	109.5
C8—C7—C9	108.84 (14)	H24A—C24—H24B	109.5
N1—C7—C10	110.42 (13)	C23—C24—H24C	109.5
C8—C7—C10	108.40 (15)	H24A—C24—H24C	109.5
C9—C7—C10	111.48 (16)	H24B—C24—H24C	109.5
N2—C11—C13	110.27 (13)	C15—C18—H18A	109.5
N2—C11—C14	109.42 (15)	C15—C18—H18B	109.5
C13—C11—C14	108.86 (17)	H18A—C18—H18B	109.5
N2—C11—C12	109.46 (16)	C15—C18—H18C	109.5
C13—C11—C12	107.89 (16)	H18A—C18—H18C	109.5
C14—C11—C12	110.93 (16)	H18B—C18—H18C	109.5
C5—C6—C1	108.13 (16)	C19—C21—H21A	109.5
C5—C6—H6	125.9	C19—C21—H21B	109.5
C1—C6—H6	125.9	H21A—C21—H21B	109.5
N5—C23—C24	110.47 (15)	C19—C21—H21C	109.5
N5—C23—C25	109.34 (14)	H21A—C21—H21C	109.5
C24—C23—C25	108.87 (15)	H21B—C21—H21C	109.5
N5—C23—C26	109.31 (14)	C19—C20—H20A	109.5
C24—C23—C26	111.14 (16)	C19—C20—H20B	109.5
C25—C23—C26	107.64 (15)	H20A—C20—H20B	109.5
C7—C10—H10A	109.5	C19—C20—H20C	109.5
C7—C10—H10B	109.5	H20A—C20—H20C	109.5
H10A—C10—H10B	109.5	H20B—C20—H20C	109.5
C7—C10—H10C	109.5	C11—C13—H13A	109.5
H10A—C10—H10C	109.5	C11—C13—H13B	109.5
H10B—C10—H10C	109.5	H13A—C13—H13B	109.5
N4—C19—C22	111.83 (16)	C11—C13—H13C	109.5
N4—C19—C21	113.59 (14)	H13A—C13—H13C	109.5
C22—C19—C21	111.44 (17)	H13B—C13—H13C	109.5
N4—C19—C20	103.33 (17)	C11—C12—H12A	109.5
C22—C19—C20	107.70 (16)	C11—C12—H12B	109.5
C21—C19—C20	108.41 (18)	H12A—C12—H12B	109.5
C23—C26—H26A	109.5	C11—C12—H12C	109.5
C23—C26—H26B	109.5	H12A—C12—H12C	109.5
H26A—C26—H26B	109.5	H12B—C12—H12C	109.5
C23—C26—H26C	109.5	C15—C17—H17A	109.5
H26A—C26—H26C	109.5	C15—C17—H17B	109.5
H26B—C26—H26C	109.5	H17A—C17—H17B	109.5
N3—C15—C16	110.14 (15)	C15—C17—H17C	109.5
N3—C15—C18	111.24 (15)	H17A—C17—H17C	109.5
C16—C15—C18	109.52 (17)	H17B—C17—H17C	109.5
N3—C15—C17	105.99 (16)	C15—C16—H16A	109.5
C16—C15—C17	109.29 (17)	C15—C16—H16B	109.5
C18—C15—C17	110.59 (16)	H16A—C16—H16B	109.5
C19—C22—H22A	109.5	C15—C16—H16C	109.5
C19—C22—H22B	109.5	H16A—C16—H16C	109.5
H22A—C22—H22B	109.5	H16B—C16—H16C	109.5
C19—C22—H22C	109.5