N-(n-Dec-yl)-4-nitro-aniline.

N-(n-Dec-yl)-4-nitro-aniline, C(16)H(26)N(2)O(2), crystallizes with two essentially planar mol-ecules in the asymmetric unit. The decyl chains are fully extended in an anti conformation. The mol-ecules pack in planar layers, within which mol-ecules are linked into chains by two approximately linear N-H⋯O hydrogen bonds between the amine N atom and one O atom of the nitro group of an adjacent mol-ecule. These mol-ecular chains propagate via inter-leaving of the decyl chains to form the two dimensional sheets. The sheets are associated exclusively via non-bonded contacts. The structure has features in common with those of other N-alkyl-4-nitro-anilines, but also subtle differences in packing.

Related literature

For the structures of other N-alkyl-4-nitro­anilines, see: Panunto et al. (1987 ▶); Gangopadhyay et al. (1999 ▶); Teng et al. (2006 ▶).

Experimental

Crystal data

C16H26N2O2

M = 278.39

Monoclinic,

a = 13.291 (6) Å

b = 29.117 (12) Å

c = 8.279 (4) Å

β = 91.457 (7)°

V = 3203 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 140 (2) K

0.40 × 0.35 × 0.28 mm

Data collection

Bruker SMART 6000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶; Blessing, 1995 ▶) T min = 0.94, T max = 0.98

28685 measured reflections

6310 independent reflections

4359 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.140

S = 1.03

6310 reflections

569 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenberg & Berndt, 2006 ▶) and Crystal Maker (Crystal Maker, 2006 ▶); software used to prepare material for publication: SHELTXL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003310/lh2595sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003310/lh2595Isup2.hkl

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

C16H26N2O2	F000 = 1216
Mr = 278.39	Dx = 1.155 Mg m−3
Monoclinic, P21/c	Melting point = 332–333 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 13.291 (6) Å	Cell parameters from 950 reflections
b = 29.117 (12) Å	θ = 2.6–25.8º
c = 8.279 (4) Å	µ = 0.08 mm−1
β = 91.457 (7)º	T = 140 (2) K
V = 3203 (2) Å3	Pyramidal, yellow
Z = 8	0.40 × 0.35 × 0.28 mm

Bruker SMART 6000 CCD diffractometer	6310 independent reflections
Radiation source: fine-focus sealed tube	4359 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 140(2) K	θmax = 26.1º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996; Blessing, 1995)	h = −16→16
Tmin = 0.94, Tmax = 0.98	k = −32→35
28685 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	All H-atom parameters refined
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.231P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6310 reflections	Δρmax = 0.19 e Å−3
569 parameters	Δρmin = −0.26 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
O1	−0.60160 (9)	0.67377 (4)	−0.86284 (15)	0.0412 (3)
O2	−0.67258 (9)	0.60818 (4)	−0.90706 (16)	0.0453 (4)
O3	1.10779 (9)	0.09460 (4)	0.85523 (15)	0.0406 (3)
O4	1.17105 (10)	0.16069 (4)	0.91774 (17)	0.0484 (4)
N1	−0.60284 (10)	0.63137 (5)	−0.85126 (16)	0.0302 (3)
N2	−0.27827 (10)	0.54358 (5)	−0.54454 (16)	0.0295 (3)
N3	1.10435 (10)	0.13712 (5)	0.85407 (16)	0.0320 (3)
N4	0.77760 (11)	0.22343 (5)	0.54846 (17)	0.0312 (3)
C1	−0.51989 (11)	0.60874 (6)	−0.77006 (18)	0.0256 (4)
C2	−0.51950 (12)	0.56106 (6)	−0.75980 (19)	0.0276 (4)
C3	−0.44015 (12)	0.53898 (6)	−0.68323 (19)	0.0265 (4)
C4	−0.35872 (11)	0.56424 (5)	−0.61648 (18)	0.0246 (4)
C5	−0.36234 (12)	0.61265 (6)	−0.62760 (19)	0.0274 (4)
C6	−0.44100 (12)	0.63459 (6)	−0.70329 (19)	0.0273 (4)
C7	−0.26796 (13)	0.49425 (6)	−0.5227 (2)	0.0283 (4)
C8	−0.16565 (13)	0.48362 (6)	−0.4446 (2)	0.0300 (4)
C9	−0.14962 (13)	0.43315 (6)	−0.4047 (2)	0.0295 (4)
C10	−0.04873 (13)	0.42560 (6)	−0.3167 (2)	0.0317 (4)
C11	−0.02331 (13)	0.37619 (6)	−0.2754 (2)	0.0292 (4)
C12	0.07786 (13)	0.37202 (6)	−0.1859 (2)	0.0296 (4)
C13	0.10972 (13)	0.32300 (6)	−0.1464 (2)	0.0290 (4)
C14	0.20989 (13)	0.31956 (6)	−0.0544 (2)	0.0310 (4)
C15	0.24269 (14)	0.27065 (6)	−0.0180 (2)	0.0354 (4)
C16	0.34653 (16)	0.26753 (8)	0.0615 (3)	0.0499 (6)
C17	1.01992 (12)	0.15945 (6)	0.77582 (18)	0.0271 (4)
C18	1.01434 (12)	0.20703 (6)	0.77712 (19)	0.0289 (4)
C19	0.93436 (12)	0.22876 (6)	0.70194 (19)	0.0289 (4)
C20	0.85730 (11)	0.20307 (6)	0.62333 (18)	0.0264 (4)
C21	0.86534 (12)	0.15453 (6)	0.62463 (19)	0.0283 (4)
C22	0.94510 (12)	0.13317 (6)	0.69935 (19)	0.0275 (4)
C23	0.76177 (13)	0.27270 (6)	0.5393 (2)	0.0295 (4)
C24	0.66360 (13)	0.28244 (6)	0.4467 (2)	0.0312 (4)
C25	0.64562 (13)	0.33306 (6)	0.4121 (2)	0.0297 (4)
C26	0.54838 (13)	0.34037 (6)	0.3138 (2)	0.0310 (4)
C27	0.52284 (13)	0.39032 (6)	0.2770 (2)	0.0307 (4)
C28	0.42175 (13)	0.39529 (6)	0.1880 (2)	0.0294 (4)
C29	0.39176 (13)	0.44438 (6)	0.1484 (2)	0.0286 (4)
C30	0.29031 (13)	0.44809 (6)	0.0593 (2)	0.0292 (4)
C31	0.26026 (14)	0.49683 (6)	0.0147 (2)	0.0323 (4)
C32	0.15712 (16)	0.49976 (7)	−0.0678 (3)	0.0420 (5)
H2N	−0.2325 (13)	0.5606 (6)	−0.496 (2)	0.032 (5)*
H2	−0.5723 (13)	0.5437 (6)	−0.8041 (19)	0.027 (4)*
H3	−0.4412 (13)	0.5071 (7)	−0.679 (2)	0.035 (5)*
H4N	0.7319 (14)	0.2059 (7)	0.504 (2)	0.037 (5)*
H5	−0.3087 (13)	0.6296 (6)	−0.5867 (19)	0.030 (5)*
H6	−0.4425 (13)	0.6666 (7)	−0.7100 (19)	0.031 (5)*
H7B	−0.3219 (13)	0.4826 (6)	−0.453 (2)	0.031 (4)*
H7A	−0.2746 (12)	0.4790 (6)	−0.630 (2)	0.027 (4)*
H8B	−0.1144 (13)	0.4933 (6)	−0.519 (2)	0.034 (5)*
H8A	−0.1593 (13)	0.5016 (6)	−0.347 (2)	0.039 (5)*
H9B	−0.2026 (13)	0.4221 (6)	−0.334 (2)	0.035 (5)*
H9A	−0.1528 (12)	0.4146 (6)	−0.507 (2)	0.033 (5)*
H10B	0.0036 (13)	0.4388 (6)	−0.385 (2)	0.034 (5)*
H10A	−0.0496 (13)	0.4451 (6)	−0.220 (2)	0.038 (5)*
H11B	−0.0757 (13)	0.3637 (6)	−0.205 (2)	0.030 (4)*
H11A	−0.0216 (12)	0.3566 (6)	−0.376 (2)	0.033 (5)*
H12B	0.1303 (13)	0.3863 (6)	−0.251 (2)	0.035 (5)*
H12A	0.0726 (12)	0.3896 (6)	−0.083 (2)	0.031 (4)*
H13B	0.0577 (13)	0.3094 (6)	−0.083 (2)	0.033 (5)*
H13A	0.1142 (12)	0.3066 (6)	−0.246 (2)	0.036 (5)*
H14B	0.2036 (12)	0.3372 (6)	0.047 (2)	0.031 (4)*
H14A	0.2602 (14)	0.3339 (6)	−0.121 (2)	0.044 (5)*
H15B	0.2401 (15)	0.2530 (7)	−0.116 (3)	0.054 (6)*
H15A	0.1955 (14)	0.2567 (6)	0.052 (2)	0.039 (5)*
H16C	0.3993 (16)	0.2807 (8)	−0.007 (3)	0.064 (7)*
H16B	0.3464 (18)	0.2856 (9)	0.166 (3)	0.079 (8)*
H16A	0.3665 (16)	0.2361 (9)	0.085 (3)	0.063 (7)*
H18	1.0663 (14)	0.2236 (6)	0.829 (2)	0.037 (5)*
H19	0.9313 (13)	0.2604 (7)	0.705 (2)	0.038 (5)*
H21	0.8145 (13)	0.1366 (6)	0.578 (2)	0.036 (5)*
H22	0.9501 (12)	0.1018 (6)	0.6989 (18)	0.021 (4)*
H23A	0.7597 (13)	0.2854 (6)	0.650 (2)	0.035 (5)*
H23B	0.8176 (12)	0.2866 (6)	0.4814 (19)	0.026 (4)*
H24A	0.6678 (13)	0.2668 (6)	0.346 (2)	0.035 (5)*
H24B	0.6091 (13)	0.2712 (6)	0.511 (2)	0.037 (5)*
H25A	0.6444 (12)	0.3504 (6)	0.512 (2)	0.029 (4)*
H25B	0.7028 (14)	0.3458 (6)	0.351 (2)	0.041 (5)*
H26B	0.5542 (13)	0.3223 (6)	0.212 (2)	0.038 (5)*
H26A	0.4937 (14)	0.3258 (6)	0.375 (2)	0.039 (5)*
H27A	0.5216 (13)	0.4080 (6)	0.380 (2)	0.035 (5)*
H27B	0.5763 (14)	0.4048 (6)	0.210 (2)	0.035 (5)*
H28B	0.3706 (13)	0.3813 (6)	0.257 (2)	0.032 (5)*
H28A	0.4228 (13)	0.3761 (6)	0.087 (2)	0.037 (5)*
H29B	0.4433 (13)	0.4581 (6)	0.0850 (19)	0.034 (5)*
H29A	0.3906 (12)	0.4617 (6)	0.252 (2)	0.030 (4)*
H30B	0.2386 (13)	0.4343 (6)	0.131 (2)	0.033 (5)*
H30A	0.2948 (13)	0.4291 (6)	−0.039 (2)	0.034 (5)*
H31B	0.2590 (13)	0.5154 (6)	0.110 (2)	0.031 (4)*
H31A	0.3098 (14)	0.5093 (7)	−0.057 (2)	0.045 (5)*
H32C	0.1556 (15)	0.4806 (7)	−0.168 (2)	0.054 (6)*
H32B	0.1019 (17)	0.4875 (8)	0.003 (3)	0.066 (7)*
H32A	0.1373 (15)	0.5321 (8)	−0.101 (2)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0429 (8)	0.0236 (7)	0.0564 (8)	0.0058 (5)	−0.0149 (6)	0.0077 (6)
O2	0.0334 (7)	0.0367 (8)	0.0647 (9)	−0.0033 (6)	−0.0236 (6)	0.0049 (6)
O3	0.0417 (7)	0.0266 (8)	0.0528 (8)	0.0096 (6)	−0.0097 (6)	0.0047 (6)
O4	0.0381 (8)	0.0369 (8)	0.0688 (9)	−0.0005 (6)	−0.0288 (7)	0.0033 (6)
N1	0.0289 (8)	0.0277 (9)	0.0339 (7)	0.0015 (6)	−0.0054 (6)	0.0025 (6)
N2	0.0261 (8)	0.0215 (8)	0.0402 (8)	−0.0022 (6)	−0.0109 (6)	0.0010 (6)
N3	0.0307 (8)	0.0276 (9)	0.0373 (8)	0.0045 (7)	−0.0060 (6)	0.0035 (6)
N4	0.0268 (8)	0.0247 (8)	0.0416 (8)	0.0013 (6)	−0.0113 (6)	−0.0014 (6)
C1	0.0257 (8)	0.0236 (9)	0.0273 (8)	0.0026 (7)	−0.0036 (7)	0.0023 (6)
C2	0.0243 (9)	0.0242 (10)	0.0340 (9)	−0.0036 (7)	−0.0044 (7)	−0.0016 (7)
C3	0.0274 (9)	0.0175 (9)	0.0345 (9)	0.0004 (7)	−0.0048 (7)	0.0010 (7)
C4	0.0229 (8)	0.0241 (9)	0.0265 (8)	0.0007 (7)	−0.0023 (6)	0.0011 (6)
C5	0.0258 (9)	0.0252 (10)	0.0308 (9)	−0.0049 (7)	−0.0039 (7)	−0.0005 (7)
C6	0.0318 (9)	0.0195 (9)	0.0304 (8)	−0.0006 (7)	−0.0015 (7)	0.0011 (7)
C7	0.0263 (9)	0.0216 (9)	0.0367 (9)	0.0006 (7)	−0.0049 (7)	0.0015 (7)
C8	0.0287 (9)	0.0241 (9)	0.0369 (10)	0.0006 (7)	−0.0060 (8)	0.0031 (8)
C9	0.0285 (9)	0.0231 (9)	0.0366 (10)	0.0006 (7)	−0.0039 (8)	0.0009 (7)
C10	0.0305 (9)	0.0235 (10)	0.0408 (10)	0.0002 (7)	−0.0062 (8)	0.0019 (8)
C11	0.0294 (9)	0.0237 (10)	0.0343 (9)	0.0020 (7)	−0.0033 (8)	0.0017 (7)
C12	0.0300 (9)	0.0216 (9)	0.0371 (9)	−0.0001 (7)	−0.0032 (8)	0.0031 (7)
C13	0.0293 (9)	0.0222 (9)	0.0352 (9)	0.0014 (7)	−0.0028 (7)	0.0016 (7)
C14	0.0286 (9)	0.0254 (10)	0.0388 (10)	0.0008 (7)	−0.0028 (8)	0.0050 (8)
C15	0.0352 (10)	0.0241 (10)	0.0466 (11)	0.0016 (8)	−0.0081 (9)	0.0049 (8)
C16	0.0400 (12)	0.0368 (13)	0.0719 (16)	0.0049 (10)	−0.0178 (11)	0.0130 (11)
C17	0.0253 (9)	0.0258 (10)	0.0301 (8)	0.0034 (7)	−0.0029 (7)	0.0031 (7)
C18	0.0263 (9)	0.0258 (10)	0.0343 (9)	−0.0030 (7)	−0.0076 (7)	0.0007 (7)
C19	0.0300 (9)	0.0204 (10)	0.0361 (9)	0.0009 (7)	−0.0056 (7)	0.0008 (7)
C20	0.0238 (8)	0.0276 (10)	0.0277 (8)	0.0030 (7)	−0.0014 (6)	0.0017 (6)
C21	0.0260 (9)	0.0261 (10)	0.0325 (9)	−0.0031 (7)	−0.0041 (7)	−0.0024 (7)
C22	0.0312 (9)	0.0179 (10)	0.0334 (9)	0.0018 (7)	−0.0011 (7)	−0.0002 (7)
C23	0.0292 (9)	0.0250 (10)	0.0339 (9)	0.0028 (7)	−0.0046 (7)	0.0013 (7)
C24	0.0285 (9)	0.0277 (10)	0.0372 (10)	0.0030 (7)	−0.0039 (8)	−0.0004 (8)
C25	0.0291 (9)	0.0269 (10)	0.0330 (9)	0.0042 (7)	−0.0027 (7)	−0.0012 (7)
C26	0.0330 (10)	0.0255 (10)	0.0342 (9)	0.0049 (8)	−0.0056 (8)	−0.0015 (7)
C27	0.0315 (10)	0.0262 (10)	0.0342 (9)	0.0030 (7)	−0.0042 (8)	0.0003 (7)
C28	0.0325 (9)	0.0231 (9)	0.0323 (9)	0.0025 (7)	−0.0053 (7)	−0.0004 (7)
C29	0.0299 (9)	0.0234 (10)	0.0322 (9)	0.0001 (7)	−0.0041 (7)	−0.0003 (7)
C30	0.0315 (9)	0.0212 (9)	0.0344 (9)	0.0002 (7)	−0.0056 (8)	0.0004 (7)
C31	0.0352 (10)	0.0239 (10)	0.0374 (10)	0.0016 (8)	−0.0067 (8)	−0.0018 (8)
C32	0.0398 (11)	0.0317 (12)	0.0536 (12)	0.0067 (9)	−0.0155 (9)	−0.0001 (9)

O1—N1	1.2383 (18)	C15—C16	1.516 (3)
O2—N1	1.2275 (17)	C15—H15B	0.96 (2)
O3—N3	1.2389 (19)	C15—H15A	0.954 (19)
O4—N3	1.2293 (18)	C16—H16C	0.99 (2)
N1—C1	1.437 (2)	C16—H16B	1.01 (2)
N2—C4	1.352 (2)	C16—H16A	0.97 (2)
N2—C7	1.454 (2)	C17—C18	1.387 (2)
N2—H2N	0.873 (18)	C17—C22	1.394 (2)
N3—C17	1.437 (2)	C18—C19	1.373 (2)
N4—C20	1.351 (2)	C18—H18	0.938 (19)
N4—C23	1.452 (2)	C19—C20	1.414 (2)
N4—H4N	0.869 (19)	C19—H19	0.92 (2)
C1—C2	1.391 (2)	C20—C21	1.417 (2)
C1—C6	1.394 (2)	C21—C22	1.364 (2)
C2—C3	1.376 (2)	C21—H21	0.930 (18)
C2—H2	0.933 (17)	C22—H22	0.916 (18)
C3—C4	1.410 (2)	C23—C24	1.523 (2)
C3—H3	0.930 (19)	C23—H23A	0.987 (17)
C4—C5	1.413 (2)	C23—H23B	0.982 (17)
C5—C6	1.364 (2)	C24—C25	1.519 (2)
C5—H5	0.924 (17)	C24—H24A	0.957 (18)
C6—H6	0.935 (19)	C24—H24B	0.966 (18)
C7—C8	1.523 (2)	C25—C26	1.524 (2)
C7—H7B	0.989 (17)	C25—H25A	0.970 (17)
C7—H7A	0.997 (16)	C25—H25B	0.995 (19)
C8—C9	1.520 (2)	C26—C27	1.522 (2)
C8—H8B	0.973 (18)	C26—H26B	1.000 (18)
C8—H8A	0.965 (18)	C26—H26A	0.992 (18)
C9—C10	1.526 (2)	C27—C28	1.523 (2)
C9—H9B	0.982 (18)	C27—H27A	0.999 (18)
C9—H9A	1.002 (17)	C27—H27B	1.003 (18)
C10—C11	1.515 (2)	C28—C29	1.518 (2)
C10—H10B	0.986 (17)	C28—H28B	0.988 (17)
C10—H10A	0.984 (18)	C28—H28A	1.008 (17)
C11—C12	1.524 (2)	C29—C30	1.524 (2)
C11—H11B	0.989 (17)	C29—H29B	0.961 (18)
C11—H11A	1.012 (17)	C29—H29A	0.995 (17)
C12—C13	1.522 (2)	C30—C31	1.518 (2)
C12—H12B	0.985 (18)	C30—H30B	1.003 (17)
C12—H12A	1.000 (17)	C30—H30A	0.983 (18)
C13—C14	1.520 (2)	C31—C32	1.518 (3)
C13—H13B	0.964 (17)	C31—H31B	0.957 (17)
C13—H13A	0.959 (18)	C31—H31A	0.968 (19)
C14—C15	1.517 (3)	C32—H32C	1.00 (2)
C14—H14B	0.988 (17)	C32—H32B	1.02 (2)
C14—H14A	0.973 (19)	C32—H32A	1.01 (2)
O2—N1—O1	122.05 (13)	C15—C16—H16C	112.1 (12)
O2—N1—C1	119.14 (14)	C15—C16—H16B	108.6 (14)
O1—N1—C1	118.81 (13)	H16C—C16—H16B	107.8 (19)
C4—N2—C7	124.44 (14)	C15—C16—H16A	112.5 (13)
C4—N2—H2N	119.0 (12)	H16C—C16—H16A	106.6 (18)
C7—N2—H2N	116.1 (12)	H16B—C16—H16A	109.1 (19)
O4—N3—O3	121.91 (14)	C18—C17—C22	120.94 (14)
O4—N3—C17	119.14 (15)	C18—C17—N3	119.32 (14)
O3—N3—C17	118.95 (14)	C22—C17—N3	119.74 (15)
C20—N4—C23	124.66 (15)	C19—C18—C17	119.84 (15)
C20—N4—H4N	118.1 (12)	C19—C18—H18	121.6 (11)
C23—N4—H4N	117.3 (12)	C17—C18—H18	118.6 (11)
C2—C1—C6	120.88 (14)	C18—C19—C20	120.58 (16)
C2—C1—N1	119.20 (14)	C18—C19—H19	118.8 (11)
C6—C1—N1	119.91 (15)	C20—C19—H19	120.6 (11)
C3—C2—C1	119.74 (15)	N4—C20—C19	121.98 (16)
C3—C2—H2	119.2 (11)	N4—C20—C21	119.95 (15)
C1—C2—H2	121.1 (10)	C19—C20—C21	118.07 (14)
C2—C3—C4	120.57 (16)	C22—C21—C20	121.05 (15)
C2—C3—H3	118.2 (11)	C22—C21—H21	118.6 (11)
C4—C3—H3	121.2 (11)	C20—C21—H21	120.3 (11)
N2—C4—C3	122.09 (15)	C21—C22—C17	119.53 (16)
N2—C4—C5	119.85 (14)	C21—C22—H22	120.5 (10)
C3—C4—C5	118.06 (14)	C17—C22—H22	119.9 (10)
C6—C5—C4	121.42 (15)	N4—C23—C24	109.36 (14)
C6—C5—H5	119.6 (11)	N4—C23—H23A	109.2 (10)
C4—C5—H5	119.0 (11)	C24—C23—H23A	110.7 (10)
C5—C6—C1	119.31 (16)	N4—C23—H23B	108.9 (10)
C5—C6—H6	120.6 (11)	C24—C23—H23B	109.0 (9)
C1—C6—H6	120.0 (11)	H23A—C23—H23B	109.7 (14)
N2—C7—C8	109.51 (13)	C25—C24—C23	113.85 (14)
N2—C7—H7B	110.0 (10)	C25—C24—H24A	108.0 (11)
C8—C7—H7B	109.6 (10)	C23—C24—H24A	106.4 (11)
N2—C7—H7A	108.8 (9)	C25—C24—H24B	108.5 (10)
C8—C7—H7A	110.3 (9)	C23—C24—H24B	107.9 (10)
H7B—C7—H7A	108.5 (13)	H24A—C24—H24B	112.3 (15)
C9—C8—C7	114.04 (14)	C24—C25—C26	111.31 (14)
C9—C8—H8B	108.7 (10)	C24—C25—H25A	110.4 (10)
C7—C8—H8B	107.6 (10)	C26—C25—H25A	110.5 (10)
C9—C8—H8A	109.4 (11)	C24—C25—H25B	109.9 (11)
C7—C8—H8A	107.7 (11)	C26—C25—H25B	108.9 (10)
H8B—C8—H8A	109.2 (15)	H25A—C25—H25B	105.6 (14)
C8—C9—C10	111.07 (14)	C27—C26—C25	114.96 (14)
C8—C9—H9B	110.3 (10)	C27—C26—H26B	110.8 (10)
C10—C9—H9B	107.6 (10)	C25—C26—H26B	107.1 (10)
C8—C9—H9A	109.6 (10)	C27—C26—H26A	110.3 (11)
C10—C9—H9A	110.0 (10)	C25—C26—H26A	106.8 (10)
H9B—C9—H9A	108.1 (14)	H26B—C26—H26A	106.4 (14)
C11—C10—C9	115.65 (14)	C26—C27—C28	112.15 (14)
C11—C10—H10B	110.1 (10)	C26—C27—H27A	109.2 (10)
C9—C10—H10B	107.1 (10)	C28—C27—H27A	109.4 (10)
C11—C10—H10A	111.7 (11)	C26—C27—H27B	110.7 (10)
C9—C10—H10A	106.2 (10)	C28—C27—H27B	108.9 (10)
H10B—C10—H10A	105.6 (14)	H27A—C27—H27B	106.4 (14)
C10—C11—C12	111.98 (14)	C29—C28—C27	114.68 (14)
C10—C11—H11B	109.0 (10)	C29—C28—H28B	109.4 (10)
C12—C11—H11B	108.0 (9)	C27—C28—H28B	106.9 (9)
C10—C11—H11A	111.0 (10)	C29—C28—H28A	110.6 (10)
C12—C11—H11A	108.6 (9)	C27—C28—H28A	108.6 (10)
H11B—C11—H11A	108.1 (14)	H28B—C28—H28A	106.2 (14)
C13—C12—C11	114.60 (14)	C28—C29—C30	113.29 (14)
C13—C12—H12B	108.4 (10)	C28—C29—H29B	108.8 (11)
C11—C12—H12B	109.0 (10)	C30—C29—H29B	109.9 (10)
C13—C12—H12A	108.7 (10)	C28—C29—H29A	107.5 (9)
C11—C12—H12A	107.2 (10)	C30—C29—H29A	110.4 (9)
H12B—C12—H12A	108.7 (14)	H29B—C29—H29A	106.7 (14)
C14—C13—C12	113.87 (14)	C31—C30—C29	114.08 (14)
C14—C13—H13B	109.3 (10)	C31—C30—H30B	109.7 (10)
C12—C13—H13B	107.6 (10)	C29—C30—H30B	107.2 (9)
C14—C13—H13A	109.1 (10)	C31—C30—H30A	110.2 (10)
C12—C13—H13A	107.7 (11)	C29—C30—H30A	106.7 (10)
H13B—C13—H13A	109.2 (14)	H30B—C30—H30A	108.7 (14)
C15—C14—C13	113.89 (15)	C30—C31—C32	113.01 (15)
C15—C14—H14B	110.5 (10)	C30—C31—H31B	109.7 (10)
C13—C14—H14B	107.4 (10)	C32—C31—H31B	107.8 (10)
C15—C14—H14A	108.6 (11)	C30—C31—H31A	108.8 (12)
C13—C14—H14A	107.0 (11)	C32—C31—H31A	108.9 (11)
H14B—C14—H14A	109.4 (15)	H31B—C31—H31A	108.6 (16)
C16—C15—C14	113.34 (16)	C31—C32—H32C	110.0 (12)
C16—C15—H15B	110.3 (12)	C31—C32—H32B	112.1 (12)
C14—C15—H15B	109.3 (12)	H32C—C32—H32B	106.6 (17)
C16—C15—H15A	108.5 (11)	C31—C32—H32A	113.5 (12)
C14—C15—H15A	109.2 (11)	H32C—C32—H32A	106.9 (16)
H15B—C15—H15A	106.0 (17)	H32B—C32—H32A	107.3 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3i	0.873 (18)	2.234 (19)	3.101 (2)	171.7 (16)
N4—H4N···O1ii	0.869 (19)	2.265 (19)	3.121 (2)	168.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3i	0.873 (18)	2.234 (19)	3.101 (2)	171.7 (16)
N4—H4N⋯O1ii	0.869 (19)	2.265 (19)	3.121 (2)	168.3 (17)

Symmetry codes: (i) ; (ii) .