m-Phenyl-enediamine.

In the title compound, C(6)H(8)N(2), there are four mol-ecules in the asymmetric unit, with each mol-ecule, including the H atoms on the N atoms of the amino groups, showing local C2 symmetry. In the crystal structure, all except one of the NH(2) groups participate in N-H⋯O hydrogen bonding. The identified hydrogen bonds furnish a three-dimensional network. N-H⋯π contacts are observed with H⋯π distances ranging from 2.516 (17) to 2.815 (16) Å. No π-stacking of the aromatic rings is observed.

Related literature

For the crystal structures of a series of meta-phenyl­enediamine salts derived from mineralic acids, see: Anderson et al. (2006 ▶).

Experimental

Crystal data

C6H8N2

M = 108.14

Monoclinic,

a = 8.1350 (4) Å

b = 12.0080 (6) Å

c = 23.9003 (16) Å

β = 90.818 (5)°

V = 2334.5 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 200 (2) K

0.32 × 0.26 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.976, T max = 0.983

13102 measured reflections

4681 independent reflections

2852 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 0.96

4681 reflections

354 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039950/ez2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039950/ez2150Isup2.hkl

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

C6H8N2	F000 = 928
Mr = 108.14	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4885 reflections
a = 8.1350 (4) Å	θ = 3.8–26.3º
b = 12.0080 (6) Å	µ = 0.08 mm−1
c = 23.9003 (16) Å	T = 200 (2) K
β = 90.818 (5)º	Block, colourless
V = 2334.5 (2) Å3	0.32 × 0.26 × 0.22 mm
Z = 16

Nonius KappaCCD diffractometer	4681 independent reflections
Radiation source: fine-focus sealed tube	2852 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 200(2) K	θmax = 26.3º
ω scans	θmin = 3.8º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2005)	h = −9→10
Tmin = 0.976, Tmax = 0.983	k = −12→14
13102 measured reflections	l = −21→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
4681 reflections	Δρmax = 0.14 e Å−3
354 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. CrysAlis RED (Oxford Diffraction, 2007) Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02); empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

	x	y	z	Uiso*/Ueq
N11	1.03776 (15)	0.37351 (12)	0.21676 (6)	0.0396 (3)
H111	1.106 (2)	0.3310 (14)	0.2386 (7)	0.066 (6)*
H112	1.090 (2)	0.4292 (14)	0.2015 (7)	0.058 (5)*
N13	0.77815 (16)	0.02743 (10)	0.16438 (6)	0.0382 (3)
H131	0.7741 (19)	0.0134 (14)	0.2041 (7)	0.064 (5)*
H132	0.6940 (17)	−0.0005 (12)	0.1465 (6)	0.043 (4)*
N21	0.23465 (16)	0.00605 (10)	0.20759 (7)	0.0402 (3)
H211	0.1570 (18)	−0.0254 (13)	0.2248 (6)	0.045 (5)*
H212	0.2143 (18)	0.0130 (13)	0.1690 (7)	0.057 (5)*
N23	0.52866 (15)	0.35624 (11)	0.19857 (7)	0.0412 (3)
H231	0.598 (2)	0.3932 (14)	0.2199 (7)	0.065 (6)*
H232	0.578 (2)	0.3300 (14)	0.1684 (8)	0.061 (6)*
N31	−0.00400 (16)	0.84886 (11)	0.09377 (7)	0.0429 (3)
H311	−0.089 (2)	0.8489 (13)	0.0677 (7)	0.062 (5)*
H312	−0.0368 (19)	0.8796 (13)	0.1259 (7)	0.055 (5)*
N33	0.30925 (14)	0.57749 (11)	0.20222 (5)	0.0336 (3)
H331	0.3507 (18)	0.6315 (13)	0.2213 (7)	0.052 (5)*
H332	0.3850 (18)	0.5226 (13)	0.1973 (6)	0.050 (5)*
N41	0.15957 (16)	0.08484 (13)	0.07526 (6)	0.0433 (3)
H411	0.088 (2)	0.1238 (14)	0.0935 (8)	0.065 (6)*
H412	0.1202 (19)	0.0188 (15)	0.0637 (7)	0.065 (6)*
N43	0.51260 (16)	0.09065 (13)	−0.08634 (5)	0.0405 (3)
H431	0.547 (2)	0.0217 (15)	−0.0778 (7)	0.066 (6)*
H432	0.595 (2)	0.1304 (14)	−0.1029 (7)	0.066 (6)*
C11	0.94747 (14)	0.31141 (11)	0.17704 (6)	0.0311 (3)
C12	0.90693 (14)	0.20145 (11)	0.18897 (6)	0.0293 (3)
H12	0.9466	0.1683	0.2226	0.0410 (10)*
C13	0.80913 (15)	0.13920 (11)	0.15233 (6)	0.0304 (3)
C14	0.75103 (16)	0.18860 (12)	0.10305 (6)	0.0352 (3)
H14	0.6827	0.1478	0.0778	0.0410 (10)*
C15	0.79373 (17)	0.29752 (13)	0.09119 (6)	0.0393 (4)
H15	0.7552	0.3306	0.0574	0.0410 (10)*
C16	0.89083 (16)	0.35915 (12)	0.12736 (6)	0.0372 (4)
H16	0.9189	0.4338	0.1184	0.0410 (10)*
C21	0.28765 (14)	0.10438 (11)	0.23325 (6)	0.0300 (3)
C22	0.38064 (14)	0.18093 (11)	0.20319 (6)	0.0289 (3)
H22	0.4021	0.1678	0.1648	0.0410 (10)*
C23	0.44212 (15)	0.27629 (11)	0.22910 (6)	0.0297 (3)
C24	0.41196 (16)	0.29445 (12)	0.28552 (6)	0.0357 (4)
H24	0.4552	0.3586	0.3038	0.0410 (10)*
C25	0.31909 (16)	0.21894 (13)	0.31482 (6)	0.0405 (4)
H25	0.2978	0.2321	0.3532	0.0410 (10)*
C26	0.25634 (16)	0.12459 (12)	0.28946 (6)	0.0362 (4)
H26	0.1920	0.0736	0.3103	0.0410 (10)*
C31	0.07237 (15)	0.74448 (11)	0.09888 (6)	0.0320 (3)
C32	0.15676 (14)	0.71468 (11)	0.14764 (6)	0.0299 (3)
H32	0.1594	0.7644	0.1786	0.0410 (10)*
C33	0.23748 (14)	0.61256 (11)	0.15155 (6)	0.0273 (3)
C34	0.23643 (16)	0.54176 (11)	0.10574 (6)	0.0332 (3)
H34	0.2934	0.4727	0.1075	0.0410 (10)*
C35	0.15223 (17)	0.57196 (12)	0.05746 (6)	0.0409 (4)
H35	0.1512	0.5228	0.0263	0.0410 (10)*
C36	0.06989 (16)	0.67165 (13)	0.05351 (6)	0.0394 (4)
H36	0.0118	0.6907	0.0201	0.0410 (10)*
C41	0.25635 (15)	0.14386 (11)	0.03778 (6)	0.0305 (3)
C42	0.33350 (14)	0.08948 (11)	−0.00610 (5)	0.0292 (3)
H42	0.3138	0.0124	−0.0121	0.0410 (10)*
C43	0.43931 (15)	0.14666 (12)	−0.04143 (6)	0.0308 (3)
C44	0.46499 (17)	0.25939 (12)	−0.03324 (6)	0.0398 (4)
H44	0.5361	0.2996	−0.0571	0.0410 (10)*
C45	0.38627 (17)	0.31313 (12)	0.00996 (7)	0.0434 (4)
H45	0.4036	0.3907	0.0153	0.0410 (10)*
C46	0.28314 (17)	0.25683 (12)	0.04560 (6)	0.0391 (4)
H46	0.2310	0.2952	0.0752	0.0410 (10)*

	U11	U22	U33	U12	U13	U23
N11	0.0309 (7)	0.0345 (8)	0.0532 (9)	−0.0038 (6)	−0.0011 (6)	−0.0040 (7)
N13	0.0419 (7)	0.0308 (8)	0.0417 (9)	−0.0045 (6)	−0.0016 (7)	−0.0037 (7)
N21	0.0367 (7)	0.0323 (8)	0.0517 (10)	−0.0029 (6)	0.0013 (7)	−0.0033 (7)
N23	0.0341 (7)	0.0324 (8)	0.0574 (10)	−0.0009 (6)	0.0063 (7)	−0.0003 (7)
N31	0.0403 (8)	0.0411 (8)	0.0473 (9)	0.0083 (6)	−0.0009 (7)	0.0068 (7)
N33	0.0347 (7)	0.0307 (7)	0.0353 (8)	−0.0010 (6)	−0.0039 (6)	−0.0004 (6)
N41	0.0437 (8)	0.0442 (9)	0.0424 (8)	0.0016 (7)	0.0161 (7)	−0.0032 (7)
N43	0.0426 (7)	0.0511 (9)	0.0278 (7)	0.0070 (7)	0.0069 (6)	0.0031 (7)
C11	0.0222 (6)	0.0340 (8)	0.0372 (8)	0.0024 (6)	0.0068 (6)	−0.0039 (7)
C12	0.0239 (6)	0.0332 (8)	0.0309 (8)	0.0042 (6)	0.0014 (6)	0.0002 (7)
C13	0.0272 (7)	0.0319 (8)	0.0322 (8)	0.0028 (6)	0.0086 (6)	−0.0046 (7)
C14	0.0352 (8)	0.0412 (9)	0.0294 (8)	−0.0012 (6)	0.0023 (6)	−0.0060 (7)
C15	0.0422 (8)	0.0478 (10)	0.0281 (8)	0.0026 (7)	0.0056 (7)	0.0066 (7)
C16	0.0355 (8)	0.0354 (9)	0.0412 (9)	−0.0011 (6)	0.0132 (7)	0.0069 (7)
C21	0.0230 (6)	0.0298 (8)	0.0370 (9)	0.0044 (6)	−0.0037 (6)	−0.0017 (7)
C22	0.0256 (7)	0.0323 (8)	0.0287 (8)	0.0061 (6)	0.0008 (6)	−0.0037 (6)
C23	0.0225 (6)	0.0281 (8)	0.0384 (9)	0.0066 (6)	−0.0010 (6)	−0.0003 (7)
C24	0.0320 (7)	0.0366 (8)	0.0385 (9)	0.0064 (6)	−0.0062 (7)	−0.0110 (7)
C25	0.0379 (8)	0.0540 (10)	0.0295 (8)	0.0126 (7)	0.0013 (7)	−0.0067 (8)
C26	0.0320 (7)	0.0414 (9)	0.0353 (9)	0.0015 (6)	0.0039 (7)	0.0060 (7)
C31	0.0259 (7)	0.0325 (8)	0.0375 (9)	−0.0032 (6)	0.0031 (6)	0.0056 (7)
C32	0.0295 (7)	0.0299 (8)	0.0305 (8)	−0.0033 (6)	0.0027 (6)	−0.0017 (6)
C33	0.0235 (6)	0.0283 (8)	0.0301 (8)	−0.0053 (5)	0.0016 (6)	0.0024 (6)
C34	0.0374 (7)	0.0265 (8)	0.0359 (9)	−0.0003 (6)	0.0031 (7)	−0.0008 (7)
C35	0.0474 (9)	0.0428 (10)	0.0325 (9)	−0.0050 (7)	0.0011 (7)	−0.0076 (7)
C36	0.0377 (8)	0.0483 (10)	0.0321 (9)	−0.0035 (7)	−0.0043 (7)	0.0037 (8)
C41	0.0256 (7)	0.0371 (9)	0.0287 (8)	0.0027 (6)	0.0017 (6)	0.0015 (7)
C42	0.0291 (7)	0.0297 (8)	0.0288 (8)	0.0013 (6)	−0.0025 (6)	0.0003 (6)
C43	0.0276 (7)	0.0393 (9)	0.0255 (8)	0.0048 (6)	−0.0027 (6)	0.0012 (7)
C44	0.0359 (8)	0.0422 (9)	0.0414 (9)	−0.0051 (7)	0.0026 (7)	0.0061 (8)
C45	0.0484 (9)	0.0297 (9)	0.0521 (10)	−0.0027 (7)	−0.0008 (8)	−0.0025 (8)
C46	0.0409 (8)	0.0346 (9)	0.0418 (9)	0.0059 (7)	0.0034 (7)	−0.0075 (7)

N11—C11	1.4059 (18)	C15—H15	0.9500
N11—H111	0.914 (17)	C16—H16	0.9500
N11—H112	0.876 (17)	C21—C26	1.3924 (19)
N13—C13	1.3964 (18)	C21—C22	1.3960 (18)
N13—H131	0.965 (17)	C22—C23	1.3915 (18)
N13—H132	0.869 (14)	C22—H22	0.9500
N21—C21	1.3959 (18)	C23—C24	1.3913 (19)
N21—H211	0.847 (16)	C24—C25	1.378 (2)
N21—H212	0.939 (16)	C24—H24	0.9500
N23—C23	1.4016 (18)	C25—C26	1.379 (2)
N23—H231	0.876 (18)	C25—H25	0.9500
N23—H232	0.887 (18)	C26—H26	0.9500
N31—C31	1.4034 (18)	C31—C32	1.3910 (18)
N31—H311	0.922 (17)	C31—C36	1.3930 (19)
N31—H312	0.896 (17)	C32—C33	1.3935 (17)
N33—C33	1.4017 (17)	C32—H32	0.9500
N33—H331	0.860 (16)	C33—C34	1.3862 (18)
N33—H332	0.911 (16)	C34—C35	1.3818 (19)
N41—C41	1.3945 (18)	C34—H34	0.9500
N41—H411	0.868 (18)	C35—C36	1.3743 (19)
N41—H412	0.897 (18)	C35—H35	0.9500
N43—C43	1.4066 (18)	C36—H36	0.9500
N43—H431	0.895 (18)	C41—C46	1.3862 (19)
N43—H432	0.915 (18)	C41—C42	1.3925 (18)
C11—C16	1.3912 (19)	C42—C43	1.3950 (18)
C11—C12	1.3915 (18)	C42—H42	0.9500
C12—C13	1.3924 (18)	C43—C44	1.3832 (19)
C12—H12	0.9500	C44—C45	1.383 (2)
C13—C14	1.3952 (19)	C44—H44	0.9500
C14—C15	1.3837 (19)	C45—C46	1.381 (2)
C14—H14	0.9500	C45—H45	0.9500
C15—C16	1.3782 (19)	C46—H46	0.9500
C11—N11—H111	113.4 (10)	C24—C23—C22	119.55 (13)
C11—N11—H112	112.2 (11)	C24—C23—N23	119.61 (14)
H111—N11—H112	111.6 (15)	C22—C23—N23	120.79 (14)
C13—N13—H131	112.3 (10)	C25—C24—C23	119.67 (13)
C13—N13—H132	114.4 (10)	C25—C24—H24	120.2
H131—N13—H132	112.3 (14)	C23—C24—H24	120.2
C21—N21—H211	113.1 (10)	C24—C25—C26	121.30 (14)
C21—N21—H212	113.9 (10)	C24—C25—H25	119.4
H211—N21—H212	113.2 (14)	C26—C25—H25	119.4
C23—N23—H231	111.7 (12)	C25—C26—C21	119.70 (13)
C23—N23—H232	114.6 (11)	C25—C26—H26	120.2
H231—N23—H232	110.8 (16)	C21—C26—H26	120.2
C31—N31—H311	112.6 (10)	C32—C31—C36	119.49 (13)
C31—N31—H312	115.5 (10)	C32—C31—N31	121.00 (14)
H311—N31—H312	110.6 (14)	C36—C31—N31	119.44 (13)
C33—N33—H331	112.8 (10)	C31—C32—C33	120.59 (13)
C33—N33—H332	112.4 (10)	C31—C32—H32	119.7
H331—N33—H332	110.7 (14)	C33—C32—H32	119.7
C41—N41—H411	115.9 (11)	C34—C33—C32	119.29 (12)
C41—N41—H412	117.0 (11)	C34—C33—N33	119.73 (12)
H411—N41—H412	113.0 (15)	C32—C33—N33	120.82 (13)
C43—N43—H431	113.6 (11)	C35—C34—C33	119.73 (13)
C43—N43—H432	113.5 (11)	C35—C34—H34	120.1
H431—N43—H432	110.9 (15)	C33—C34—H34	120.1
C16—C11—C12	119.29 (13)	C36—C35—C34	121.42 (14)
C16—C11—N11	121.41 (13)	C36—C35—H35	119.3
C12—C11—N11	119.21 (13)	C34—C35—H35	119.3
C11—C12—C13	121.03 (12)	C35—C36—C31	119.45 (13)
C11—C12—H12	119.5	C35—C36—H36	120.3
C13—C12—H12	119.5	C31—C36—H36	120.3
C12—C13—C14	119.10 (13)	C46—C41—C42	119.26 (13)
C12—C13—N13	119.30 (13)	C46—C41—N41	119.99 (14)
C14—C13—N13	121.52 (13)	C42—C41—N41	120.67 (13)
C15—C14—C13	119.46 (13)	C41—C42—C43	120.91 (13)
C15—C14—H14	120.3	C41—C42—H42	119.5
C13—C14—H14	120.3	C43—C42—H42	119.5
C16—C15—C14	121.50 (13)	C44—C43—C42	119.30 (13)
C16—C15—H15	119.3	C44—C43—N43	120.73 (13)
C14—C15—H15	119.3	C42—C43—N43	119.90 (13)
C15—C16—C11	119.61 (13)	C45—C44—C43	119.45 (14)
C15—C16—H16	120.2	C45—C44—H44	120.3
C11—C16—H16	120.2	C43—C44—H44	120.3
C26—C21—N21	120.78 (14)	C46—C45—C44	121.61 (14)
C26—C21—C22	119.33 (13)	C46—C45—H45	119.2
N21—C21—C22	119.80 (13)	C44—C45—H45	119.2
C23—C22—C21	120.44 (13)	C45—C46—C41	119.45 (14)
C23—C22—H22	119.8	C45—C46—H46	120.3
C21—C22—H22	119.8	C41—C46—H46	120.3
C16—C11—C12—C13	−0.80 (18)	C36—C31—C32—C33	−0.47 (19)
N11—C11—C12—C13	176.01 (11)	N31—C31—C32—C33	−177.55 (12)
C11—C12—C13—C14	−0.18 (18)	C31—C32—C33—C34	1.60 (18)
C11—C12—C13—N13	176.73 (12)	C31—C32—C33—N33	−173.85 (11)
C12—C13—C14—C15	1.01 (19)	C32—C33—C34—C35	−1.62 (19)
N13—C13—C14—C15	−175.83 (12)	N33—C33—C34—C35	173.87 (12)
C13—C14—C15—C16	−0.9 (2)	C33—C34—C35—C36	0.5 (2)
C14—C15—C16—C11	−0.1 (2)	C34—C35—C36—C31	0.6 (2)
C12—C11—C16—C15	0.94 (19)	C32—C31—C36—C35	−0.6 (2)
N11—C11—C16—C15	−175.80 (12)	N31—C31—C36—C35	176.49 (12)
C26—C21—C22—C23	0.27 (18)	C46—C41—C42—C43	1.22 (18)
N21—C21—C22—C23	−176.38 (11)	N41—C41—C42—C43	−175.62 (12)
C21—C22—C23—C24	0.74 (18)	C41—C42—C43—C44	−1.28 (18)
C21—C22—C23—N23	−176.83 (11)	C41—C42—C43—N43	−178.39 (12)
C22—C23—C24—C25	−1.20 (18)	C42—C43—C44—C45	0.42 (19)
N23—C23—C24—C25	176.40 (12)	N43—C43—C44—C45	177.50 (12)
C23—C24—C25—C26	0.7 (2)	C43—C44—C45—C46	0.5 (2)
C24—C25—C26—C21	0.3 (2)	C44—C45—C46—C41	−0.5 (2)
N21—C21—C26—C25	175.81 (12)	C42—C41—C46—C45	−0.31 (19)
C22—C21—C26—C25	−0.81 (19)	N41—C41—C46—C45	176.55 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H112···N33i	0.876 (17)	2.519 (17)	3.3196 (19)	152.5 (14)
N13—H131···N33ii	0.965 (17)	2.471 (18)	3.3312 (19)	148.2 (13)
N13—H132···N43iii	0.869 (14)	2.448 (15)	3.3102 (19)	171.4 (13)
N21—H211···N11ii	0.847 (16)	2.450 (17)	3.291 (2)	172.0 (13)
N21—H212···N41	0.939 (16)	2.435 (17)	3.349 (2)	164.4 (14)
N23—H231···N21iv	0.876 (18)	2.574 (19)	3.443 (2)	171.3 (16)
N31—H312···N13v	0.896 (17)	2.510 (17)	3.2668 (19)	142.4 (13)
N33—H332···N23	0.911 (16)	2.314 (16)	3.2025 (18)	164.9 (13)
N41—H412···N31vi	0.897 (18)	2.392 (17)	3.164 (2)	144.3 (15)
N11—H111···Cg2i	0.914 (17)	2.573 (16)	3.4260 (14)	155.8 (14)
N23—H232···Cg1	0.887 (18)	2.516 (17)	3.2454 (15)	139.9 (15)
N31—H311···Cg4vii	0.922 (17)	2.815 (16)	3.7205 (16)	166.6 (13)
N33—H331···Cg2iv	0.860 (16)	2.608 (15)	3.2617 (13)	133.8 (13)
N41—H411···Cg1viii	0.868 (18)	2.707 (17)	3.5729 (15)	174.1 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H112⋯N33i	0.876 (17)	2.519 (17)	3.3196 (19)	152.5 (14)
N13—H131⋯N33ii	0.965 (17)	2.471 (18)	3.3312 (19)	148.2 (13)
N13—H132⋯N43iii	0.869 (14)	2.448 (15)	3.3102 (19)	171.4 (13)
N21—H211⋯N11ii	0.847 (16)	2.450 (17)	3.291 (2)	172.0 (13)
N21—H212⋯N41	0.939 (16)	2.435 (17)	3.349 (2)	164.4 (14)
N23—H231⋯N21iv	0.876 (18)	2.574 (19)	3.443 (2)	171.3 (16)
N31—H312⋯N13v	0.896 (17)	2.510 (17)	3.2668 (19)	142.4 (13)
N33—H332⋯N23	0.911 (16)	2.314 (16)	3.2025 (18)	164.9 (13)
N41—H412⋯N31vi	0.897 (18)	2.392 (17)	3.164 (2)	144.3 (15)
N11—H111⋯Cg2i	0.914 (17)	2.573 (16)	3.4260 (14)	155.8 (14)
N23—H232⋯Cg1	0.887 (18)	2.516 (17)	3.2454 (15)	139.9 (15)
N31—H311⋯Cg4vii	0.922 (17)	2.815 (16)	3.7205 (16)	166.6 (13)
N33—H331⋯Cg2iv	0.860 (16)	2.608 (15)	3.2617 (13)	133.8 (13)
N41—H411⋯Cg1viii	0.868 (18)	2.707 (17)	3.5729 (15)	174.1 (16)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) . C1, Cg2 and Cg4 are the centroids of the C11–C16, C21–C26 and C41–C46 phenyl rings, respectively.