tert-Butyl N-{2-[N-(N,N′-dicyclohexyl­ureido­carbonyl­ethyl)­carbamoyl]prop-2-yl}carbamate

The title compound, C₂₅H₄₄N₄O₅, exhibits a turn with the main chain reversing direction, held together by an intramol­ecular N—H...O hydrogen bond. In the urea fragment, a notable amide C—N bond between the carboxyl C and the tertiary N atom shows marked single-bond character [1.437 (2) Å]. The dihedral angle of the β-alanyl residue, centrally located in the turn, is gauche [69.2 (2)°]. The packing is mediated by two intermolecular hydrogen bonds and van der Waals contacts involving the methyl moieties and the cyclo­hexyl rings.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1994); cell refinement: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996).

Tert-butyloxycarbonyl-alpha-amino isobutyryl - beta-Alanyl - N, (N,N'-dicyclohexyl)-urea.

Crystal data

C25H44N4O5	Z = 2
Mr = 480.64	F(000) = 524
Triclinic, P1	Dx = 1.140 Mg m^−3 Dm = 1.14 Mg m^−3 Dm measured by flotation
a = 9.996 (1) Å	Cu Kα radiation, λ = 1.54180 Å
b = 10.933 (2) Å	Cell parameters from 25 reflections
c = 14.385 (3) Å	θ = 10–30°
α = 78.13 (2)°	µ = 0.64 mm^−1
β = 83.74 (1)°	T = 293 K
γ = 65.59 (1)°	Plate, colourless
V = 1400.4 (4) Å^3	0.88 × 0.63 × 0.50 mm

Data collection

CAD4 Enraf-Nonius 4-Circle automatic diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 74.7°, θmin = 3.1°
Graphite monochromator	h = 0→12
2ω scan mode	k = −12→13
5941 measured reflections	l = −15→17
5622 independent reflections	3 standard reflections every 60 reflections
4579 reflections with Fo > 4σ(Fo)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.078P)^2 + 0.1745P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.013
5622 reflections	Δρmax = 0.17 e Å^−3
475 parameters	Δρmin = −0.21 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: 0.0110 (8)

Special details

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
O1	1.04496 (11)	0.16427 (11)	0.24617 (9)	0.0604 (3)
O21	0.94105 (11)	0.01037 (11)	0.28966 (9)	0.0576 (3)
O41	1.07630 (13)	−0.33244 (12)	0.27277 (9)	0.0658 (3)
O71	0.79771 (13)	0.05107 (13)	0.02207 (9)	0.0722 (4)
O81	0.47435 (12)	−0.02808 (13)	0.23157 (9)	0.0656 (3)
N1	1.18204 (13)	−0.05515 (13)	0.24752 (10)	0.0525 (3)
N2	1.08261 (14)	−0.18473 (14)	0.14016 (10)	0.0531 (3)
N3	0.63687 (12)	0.05533 (12)	0.14459 (9)	0.0474 (3)
N4	0.67498 (13)	−0.04871 (13)	0.30272 (9)	0.0505 (3)
C1	0.91015 (17)	0.28271 (15)	0.25973 (12)	0.0541 (4)
C2	1.04679 (15)	0.03806 (15)	0.26366 (11)	0.0479 (3)
C3	1.21767 (15)	−0.20094 (15)	0.27738 (12)	0.0518 (4)
C4	1.11566 (15)	−0.24329 (14)	0.23074 (11)	0.0483 (3)
C5	0.99364 (18)	−0.22043 (19)	0.08738 (14)	0.0606 (4)
C6	0.83328 (18)	−0.16419 (17)	0.11838 (14)	0.0587 (4)
C7	0.75842 (15)	−0.01157 (16)	0.09226 (11)	0.0514 (3)
C8	0.58792 (15)	−0.01236 (14)	0.22906 (11)	0.0475 (3)
C11	0.9567 (3)	0.4003 (2)	0.2323 (2)	0.0833 (6)
C12	0.7939 (3)	0.2974 (2)	0.1939 (2)	0.0865 (7)
C31	1.2091 (3)	−0.2385 (3)	0.38450 (15)	0.0775 (6)
C32	1.37347 (19)	−0.2783 (2)	0.2400 (2)	0.0756 (6)
C81	0.53840 (15)	0.19595 (14)	0.10291 (10)	0.0462 (3)
C82	0.45236 (18)	0.19894 (16)	0.02082 (12)	0.0542 (4)
C83	0.3702 (2)	0.34637 (17)	−0.02676 (14)	0.0633 (4)
C84	0.2677 (3)	0.4297 (2)	0.04354 (16)	0.0833 (6)
C85	0.3479 (3)	0.42160 (19)	0.12907 (17)	0.0783 (6)
C86	0.4351 (2)	0.27438 (18)	0.17612 (13)	0.0595 (4)
C91	0.65535 (16)	−0.13259 (16)	0.39191 (11)	0.0523 (4)
C92	0.7236 (2)	−0.28297 (19)	0.38511 (14)	0.0677 (5)
C93	0.7050 (4)	−0.3687 (3)	0.47946 (18)	0.0918 (7)
C94	0.7701 (3)	−0.3432 (2)	0.56020 (17)	0.0889 (7)
C95	0.7042 (3)	−0.1936 (2)	0.56670 (14)	0.0768 (5)
C96	0.7207 (2)	−0.1063 (2)	0.47236 (13)	0.0637 (4)
H12	0.8302	0.3053	0.1294	0.160 (14)*
H12A	0.7069	0.3775	0.2010	0.111 (9)*
H12B	0.7707	0.2185	0.2098	0.131 (10)*
C13	0.8604 (4)	0.2695 (3)	0.3624 (2)	0.0995 (8)
H81	0.6062 (17)	0.2402 (16)	0.0774 (11)	0.045 (4)*
H82	0.521 (2)	0.1435 (19)	−0.0272 (13)	0.060 (5)*
H82A	0.379 (2)	0.1576 (18)	0.0475 (12)	0.059 (5)*
H83	0.317 (2)	0.356 (2)	−0.0842 (16)	0.083 (6)*
HN4	0.753 (2)	−0.0263 (18)	0.2942 (12)	0.055 (4)*
H5	1.025 (2)	−0.321 (2)	0.0960 (14)	0.068 (5)*
H83A	0.444 (2)	0.385 (2)	−0.0504 (14)	0.070 (5)*
H86	0.4950 (18)	0.2693 (17)	0.2283 (12)	0.052 (4)*
H96	0.826 (2)	−0.125 (2)	0.4533 (14)	0.074 (6)*
H85	0.415 (3)	0.466 (2)	0.1113 (16)	0.085 (7)*
H86A	0.369 (2)	0.2295 (19)	0.2019 (13)	0.066 (5)*
HN1	1.254 (2)	−0.0274 (19)	0.2369 (13)	0.064 (5)*
H92	0.677 (2)	−0.297 (2)	0.3289 (16)	0.080 (6)*
H31	1.227 (3)	−0.342 (3)	0.4034 (18)	0.110 (8)*
H5A	1.006 (2)	−0.184 (2)	0.0205 (16)	0.082 (6)*
H6	0.823 (2)	−0.196 (2)	0.1862 (16)	0.073 (6)*
HN2	1.116 (2)	−0.123 (2)	0.1129 (14)	0.066 (5)*
H11	0.877 (3)	0.492 (3)	0.2398 (17)	0.105 (8)*
H91	0.550 (2)	−0.1062 (17)	0.4024 (12)	0.056 (5)*
H11A	1.035 (3)	0.387 (3)	0.2679 (19)	0.106 (9)*
H85A	0.280 (3)	0.467 (3)	0.1762 (18)	0.100 (8)*
H96A	0.677 (2)	−0.009 (2)	0.4744 (15)	0.084 (6)*
H32	1.401 (3)	−0.382 (3)	0.2590 (16)	0.091 (7)*
H92A	0.830 (3)	−0.305 (2)	0.3713 (16)	0.091 (7)*
H95	0.751 (3)	−0.178 (2)	0.6179 (17)	0.086 (7)*
H6A	0.778 (3)	−0.195 (2)	0.0840 (16)	0.091 (7)*
H84	0.218 (3)	0.531 (3)	0.0144 (18)	0.100 (7)*
H94	0.754 (3)	−0.399 (3)	0.621 (2)	0.115 (9)*
H93	0.757 (3)	−0.460 (3)	0.475 (2)	0.124 (10)*
H31A	1.277 (3)	−0.210 (3)	0.4139 (18)	0.102 (8)*
H94A	0.883 (3)	−0.374 (3)	0.5458 (19)	0.108 (9)*
H93A	0.595 (3)	−0.346 (3)	0.4952 (18)	0.101 (8)*
H84A	0.190 (3)	0.397 (3)	0.0674 (18)	0.095 (7)*
H95A	0.597 (3)	−0.171 (2)	0.5825 (17)	0.093 (7)*
H32A	1.441 (3)	−0.261 (2)	0.2705 (16)	0.087 (7)*
H11B	0.979 (3)	0.407 (3)	0.163 (2)	0.108 (9)*
H32B	1.378 (3)	−0.256 (3)	0.1758 (19)	0.100 (9)*
H31B	1.114 (3)	−0.194 (3)	0.4073 (18)	0.100 (8)*
H13	0.828 (3)	0.194 (3)	0.3800 (19)	0.104 (8)*
H13A	0.777 (3)	0.358 (3)	0.3708 (19)	0.115 (9)*
H13B	0.937 (5)	0.240 (4)	0.404 (3)	0.174 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O21	0.0416 (5)	0.0556 (6)	0.0771 (8)	−0.0243 (5)	0.0075 (5)	−0.0094 (5)
N3	0.0397 (6)	0.0480 (6)	0.0487 (7)	−0.0169 (5)	−0.0046 (5)	0.0038 (5)
O81	0.0486 (6)	0.0713 (7)	0.0798 (8)	−0.0362 (5)	−0.0145 (5)	0.0134 (6)
O1	0.0457 (5)	0.0465 (6)	0.0891 (8)	−0.0206 (5)	0.0055 (5)	−0.0115 (5)
N1	0.0385 (6)	0.0476 (7)	0.0711 (8)	−0.0204 (5)	0.0034 (5)	−0.0060 (6)
O41	0.0659 (7)	0.0545 (6)	0.0794 (8)	−0.0338 (6)	−0.0089 (6)	0.0076 (5)
N4	0.0426 (6)	0.0584 (7)	0.0502 (7)	−0.0269 (6)	−0.0049 (5)	0.0069 (5)
N2	0.0452 (6)	0.0523 (7)	0.0571 (8)	−0.0176 (6)	−0.0030 (5)	−0.0035 (6)
C2	0.0418 (7)	0.0473 (7)	0.0557 (8)	−0.0209 (6)	0.0002 (6)	−0.0058 (6)
O71	0.0541 (6)	0.0726 (8)	0.0664 (8)	−0.0142 (6)	0.0094 (5)	0.0073 (6)
C8	0.0397 (6)	0.0456 (7)	0.0547 (8)	−0.0194 (6)	−0.0046 (6)	0.0030 (6)
C4	0.0398 (7)	0.0402 (7)	0.0593 (9)	−0.0134 (5)	−0.0012 (6)	−0.0029 (6)
C81	0.0449 (7)	0.0417 (7)	0.0501 (8)	−0.0188 (6)	−0.0034 (6)	−0.0001 (6)
C3	0.0419 (7)	0.0453 (7)	0.0638 (9)	−0.0161 (6)	−0.0066 (6)	−0.0006 (6)
C7	0.0408 (7)	0.0567 (8)	0.0514 (8)	−0.0166 (6)	−0.0065 (6)	−0.0017 (6)
C91	0.0445 (7)	0.0530 (8)	0.0526 (8)	−0.0209 (6)	−0.0019 (6)	0.0080 (6)
C82	0.0536 (8)	0.0454 (8)	0.0588 (9)	−0.0168 (7)	−0.0133 (7)	0.0006 (7)
C1	0.0510 (8)	0.0469 (8)	0.0609 (9)	−0.0153 (6)	−0.0003 (7)	−0.0120 (7)
C5	0.0549 (9)	0.0577 (9)	0.0627 (11)	−0.0096 (7)	−0.0043 (7)	−0.0234 (8)
C86	0.0624 (9)	0.0560 (9)	0.0553 (9)	−0.0219 (8)	0.0035 (8)	−0.0065 (7)
C6	0.0493 (8)	0.0550 (9)	0.0711 (11)	−0.0184 (7)	−0.0121 (8)	−0.0095 (8)
C83	0.0637 (10)	0.0503 (9)	0.0630 (11)	−0.0145 (8)	−0.0113 (8)	0.0046 (7)
C96	0.0701 (11)	0.0623 (10)	0.0549 (10)	−0.0263 (9)	−0.0026 (8)	−0.0024 (8)
C92	0.0798 (12)	0.0570 (10)	0.0641 (11)	−0.0290 (9)	−0.0106 (9)	0.0021 (8)
C32	0.0405 (8)	0.0585 (10)	0.124 (2)	−0.0133 (7)	−0.0047 (10)	−0.0203 (11)
C31	0.0863 (15)	0.0780 (13)	0.0654 (12)	−0.0339 (12)	−0.0231 (11)	0.0064 (10)
C84	0.0718 (12)	0.0588 (11)	0.0795 (14)	0.0021 (9)	0.0010 (10)	0.0097 (9)
C95	0.0887 (15)	0.0786 (13)	0.0504 (10)	−0.0272 (11)	−0.0052 (9)	0.0035 (9)
C11	0.0803 (14)	0.0531 (11)	0.118 (2)	−0.0281 (10)	−0.0032 (14)	−0.0162 (11)
C94	0.1117 (19)	0.0703 (13)	0.0651 (13)	−0.0264 (12)	−0.0183 (12)	0.0162 (10)
C93	0.130 (2)	0.0593 (12)	0.0827 (15)	−0.0443 (14)	−0.0155 (14)	0.0148 (10)
C85	0.0897 (14)	0.0488 (9)	0.0816 (14)	−0.0178 (9)	0.0223 (11)	−0.0147 (9)
C12	0.0782 (13)	0.0650 (12)	0.1094 (19)	−0.0209 (10)	−0.0372 (13)	0.0004 (11)
C13	0.129 (2)	0.0886 (18)	0.0775 (16)	−0.0401 (18)	0.0283 (16)	−0.0312 (13)

Geometric parameters (Å, º)

O21—C2	1.2168 (16)	C83—C84	1.511 (3)
N3—C7	1.368 (2)	C83—H83	1.00 (2)
N3—C8	1.4365 (18)	C83—H83A	0.99 (2)
N3—C81	1.4800 (18)	C96—C95	1.526 (3)
O81—C8	1.2121 (16)	C96—H96	1.01 (2)
O1—C2	1.3434 (18)	C96—H96A	0.98 (2)
O1—C1	1.4612 (18)	C92—C93	1.524 (3)
N1—C2	1.3454 (19)	C92—H92	1.05 (2)
N1—C3	1.4610 (19)	C92—H92A	0.99 (2)
N1—HN1	0.874 (19)	C32—H32	1.03 (2)
O41—C4	1.2218 (17)	C32—H32A	0.94 (2)
N4—C8	1.3342 (19)	C32—H32B	0.91 (3)
N4—C91	1.4613 (18)	C31—H31	1.05 (3)
N4—HN4	0.904 (18)	C31—H31A	1.02 (3)
N2—C4	1.339 (2)	C31—H31B	0.93 (3)
N2—C5	1.441 (2)	C84—C85	1.508 (4)
N2—HN2	0.88 (2)	C84—H84	1.02 (3)
O71—C7	1.2222 (18)	C84—H84A	0.98 (3)
C4—C3	1.540 (2)	C95—C94	1.508 (3)
C81—C86	1.521 (2)	C95—H95	0.99 (2)
C81—C82	1.522 (2)	C95—H95A	1.01 (3)
C81—H81	0.986 (16)	C11—H11	1.01 (3)
C3—C31	1.514 (3)	C11—H11A	0.93 (3)
C3—C32	1.531 (2)	C11—H11B	0.99 (3)
C7—C6	1.502 (2)	C94—C93	1.516 (4)
C91—C92	1.518 (3)	C94—H94	0.99 (3)
C91—C96	1.519 (3)	C94—H94A	1.05 (3)
C91—H91	0.974 (18)	C93—H93	0.93 (3)
C82—C83	1.522 (2)	C93—H93A	1.03 (3)
C82—H82	1.019 (19)	C85—H85	0.96 (2)
C82—H82A	1.011 (18)	C85—H85A	0.96 (3)
C1—C13	1.503 (3)	C12—H12	0.9600
C1—C11	1.506 (3)	C12—H12A	0.9600
C1—C12	1.515 (3)	C12—H12B	0.9600
C5—C6	1.513 (2)	C13—H13	0.98 (3)
C5—H5	1.00 (2)	C13—H13A	1.00 (3)
C5—H5A	0.98 (2)	C13—H13B	0.93 (4)
C86—C85	1.526 (3)	C13—C31^i	3.6042
C86—H86	0.988 (18)	C83—C6^ii	3.8540
C86—H86A	0.979 (19)	C83—C32^iii	3.7658
C6—H6	0.98 (2)	C84—C5^iv	3.8063
C6—H6A	0.97 (2)	C82—C6^ii	3.8422
C7—N3—C8	122.61 (12)	C84—C83—H83A	108.2 (12)
C7—N3—C81	117.87 (12)	C82—C83—H83A	107.8 (12)
C8—N3—C81	118.59 (11)	H83—C83—H83A	105.1 (16)
C2—O1—C1	120.94 (11)	C91—C96—C95	111.25 (16)
C2—N1—C3	120.78 (12)	C91—C96—H96	106.5 (12)
C2—N1—HN1	117.3 (13)	C95—C96—H96	112.8 (12)
C3—N1—HN1	118.9 (12)	C91—C96—H96A	109.6 (13)
C8—N4—C91	122.58 (12)	C95—C96—H96A	113.0 (13)
C8—N4—HN4	117.6 (11)	H96—C96—H96A	103.3 (17)
C91—N4—HN4	119.6 (11)	C91—C92—C93	110.41 (19)
C4—N2—C5	121.55 (15)	C91—C92—H92	108.9 (12)
C4—N2—HN2	118.6 (13)	C93—C92—H92	112.5 (12)
C5—N2—HN2	119.9 (13)	C91—C92—H92A	104.9 (13)
O21—C2—O1	125.22 (13)	C93—C92—H92A	109.5 (13)
O21—C2—N1	123.91 (14)	H92—C92—H92A	110.3 (18)
O1—C2—N1	110.86 (12)	C3—C32—H32	109.4 (13)
O81—C8—N4	124.88 (14)	C3—C32—H32A	109.4 (15)
O81—C8—N3	121.42 (13)	H32—C32—H32A	105.5 (19)
N4—C8—N3	113.63 (12)	C3—C32—H32B	110.1 (17)
O41—C4—N2	122.45 (15)	H32—C32—H32B	109 (2)
O41—C4—C3	121.08 (14)	H32A—C32—H32B	113 (2)
N2—C4—C3	116.27 (13)	C3—C31—H31	109.2 (14)
N3—C81—C86	113.02 (12)	C3—C31—H31A	109.4 (14)
N3—C81—C82	112.18 (12)	H31—C31—H31A	115.7 (19)
C86—C81—C82	110.57 (13)	C3—C31—H31B	110.6 (16)
N3—C81—H81	103.9 (9)	H31—C31—H31B	104 (2)
C86—C81—H81	108.6 (9)	H31A—C31—H31B	108 (2)
C82—C81—H81	108.3 (9)	C85—C84—C83	111.76 (18)
N1—C3—C31	111.11 (16)	C85—C84—H84	106.5 (14)
N1—C3—C32	107.57 (14)	C83—C84—H84	112.0 (14)
C31—C3—C32	110.30 (18)	C85—C84—H84A	106.8 (14)
N1—C3—C4	110.71 (12)	C83—C84—H84A	111.5 (15)
C31—C3—C4	110.64 (14)	H84—C84—H84A	108 (2)
C32—C3—C4	106.35 (15)	C94—C95—C96	111.36 (19)
O71—C7—N3	120.22 (14)	C94—C95—H95	110.0 (13)
O71—C7—C6	121.31 (15)	C96—C95—H95	110.4 (13)
N3—C7—C6	118.26 (14)	C94—C95—H95A	105.1 (14)
N4—C91—C92	111.29 (15)	C96—C95—H95A	109.6 (14)
N4—C91—C96	109.66 (13)	H95—C95—H95A	110.2 (19)
C92—C91—C96	110.86 (14)	C1—C11—H11	114.2 (14)
N4—C91—H91	106.7 (10)	C1—C11—H11A	111.2 (17)
C92—C91—H91	107.6 (10)	H11—C11—H11A	107 (2)
C96—C91—H91	110.7 (10)	C1—C11—H11B	105.6 (16)
C83—C82—C81	109.08 (14)	H11—C11—H11B	105 (2)
C83—C82—H82	110.3 (10)	H11A—C11—H11B	114 (2)
C81—C82—H82	110.9 (10)	C95—C94—C93	111.0 (2)
C83—C82—H82A	109.5 (10)	C95—C94—H94	110.9 (16)
C81—C82—H82A	108.2 (10)	C93—C94—H94	109.6 (16)
H82—C82—H82A	108.9 (14)	C95—C94—H94A	108.7 (15)
O1—C1—C13	109.85 (18)	C93—C94—H94A	107.5 (15)
O1—C1—C11	103.34 (14)	H94—C94—H94A	109 (2)
C13—C1—C11	110.5 (2)	C94—C93—C92	111.5 (2)
O1—C1—C12	109.71 (15)	C94—C93—H93	106.6 (19)
C13—C1—C12	112.3 (2)	C92—C93—H93	108.2 (19)
C11—C1—C12	110.74 (18)	C94—C93—H93A	108.3 (15)
N2—C5—C6	112.59 (14)	C92—C93—H93A	110.2 (14)
N2—C5—H5	111.7 (11)	H93—C93—H93A	112 (2)
C6—C5—H5	105.8 (11)	C84—C85—C86	112.09 (18)
N2—C5—H5A	106.7 (13)	C84—C85—H85	110.5 (14)
C6—C5—H5A	110.7 (13)	C86—C85—H85	108.3 (14)
H5—C5—H5A	109.4 (17)	C84—C85—H85A	110.7 (15)
C81—C86—C85	109.56 (15)	C86—C85—H85A	107.4 (15)
C81—C86—H86	108.0 (10)	H85—C85—H85A	108 (2)
C85—C86—H86	111.8 (10)	C1—C12—H12	109.5
C81—C86—H86A	108.4 (11)	C1—C12—H12A	109.5
C85—C86—H86A	110.5 (11)	H12—C12—H12A	109.5
H86—C86—H86A	108.5 (15)	C1—C12—H12B	109.5
C7—C6—C5	113.25 (15)	H12—C12—H12B	109.5
C7—C6—H6	112.0 (12)	H12A—C12—H12B	109.5
C5—C6—H6	110.3 (12)	C1—C13—H13	110.6 (16)
C7—C6—H6A	102.9 (14)	C1—C13—H13A	107.6 (16)
C5—C6—H6A	110.0 (14)	H13—C13—H13A	110 (2)
H6—C6—H6A	108.1 (18)	C1—C13—H13B	113 (3)
C84—C83—C82	110.87 (16)	H13—C13—H13B	101 (3)
C84—C83—H83	110.9 (13)	H13A—C13—H13B	115 (3)
C82—C83—H83	113.5 (13)
C81—N3—C7—C6	−161.89 (0.14)	C4—N2—C5—C6	72.94 (0.21)
C8—N3—C7—C6	6.88 (0.22)	C5—N2—C4—C3	177.18 (0.15)
C81—N3—C7—O71	12.91 (0.22)	O41—C4—C3—N1	−145.86 (0.15)
C8—N3—C7—O71	−178.32 (0.15)	N2—C4—C3—N1	39.03 (0.19)
C8—N3—C81—C82	−98.08 (0.16)	N2—C4—C3—C32	−77.53 (0.19)
C8—N3—C81—C86	27.76 (0.19)	O41—C4—C3—C32	97.57 (0.19)
C7—N3—C8—O81	−111.62 (0.18)	N2—C4—C3—C31	162.68 (0.16)
C81—N3—C8—O81	57.07 (0.20)	O41—C4—C3—C31	−22.22 (0.23)
C7—N3—C8—N4	71.23 (0.19)	N3—C81—C86—C85	174.82 (0.15)
C81—N3—C8—N4	−120.07 (0.15)	N3—C81—C82—C83	−172.32 (0.13)
C7—N3—C81—C86	−163.01 (0.14)	C82—C81—C86—C85	−58.48 (0.19)
C7—N3—C81—C82	71.16 (0.17)	C86—C81—C82—C83	60.52 (0.18)
C1—O1—C2—O21	1.40 (0.24)	O71—C7—C6—C5	29.68 (0.24)
C2—O1—C1—C11	−179.82 (0.16)	N3—C7—C6—C5	−155.59 (0.15)
C2—O1—C1—C12	−61.68 (0.20)	N4—C91—C92—C93	178.71 (0.18)
C2—O1—C1—C13	62.25 (0.23)	N4—C91—C96—C95	−179.24 (0.16)
C1—O1—C2—N1	−179.30 (0.13)	C96—C91—C92—C93	56.38 (0.23)
C3—N1—C2—O1	169.11 (0.13)	C92—C91—C96—C95	−55.96 (0.22)
C3—N1—C2—O21	−11.59 (0.25)	C81—C82—C83—C84	−58.33 (0.20)
C2—N1—C3—C32	174.49 (0.16)	N2—C5—C6—C7	69.16 (0.20)
C2—N1—C3—C31	−64.68 (0.21)	C81—C86—C85—C84	54.81 (0.23)
C2—N1—C3—C4	58.69 (0.19)	C82—C83—C84—C85	55.36 (0.24)
C91—N4—C8—O81	10.31 (0.25)	C91—C96—C95—C94	55.30 (0.25)
C91—N4—C8—N3	−172.65 (0.13)	C91—C92—C93—C94	−56.57 (0.28)
C8—N4—C91—C96	−155.53 (0.15)	C83—C84—C85—C86	−53.72 (0.26)
C8—N4—C91—C92	81.44 (0.19)	C96—C95—C94—C93	−54.99 (0.29)
C5—N2—C4—O41	2.15 (0.25)	C95—C94—C93—C92	55.97 (0.30)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—HN4···O21	0.90 (2)	2.07 (2)	2.964 (2)	173.39 (1.94)
N1—HN1···O81^v	0.87 (2)	2.20 (2)	3.036 (2)	161.05 (2.08)
N2—HN2···O71^iii	0.88 (2)	2.17 (2)	2.906 (2)	141.54 (1.83)

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