N-Benzyl-2-chloro-quinazolin-4-amine.

The asymmetric unit of the title compound, C15H12ClN3, contains two independent mol-ecules. The quinazoline ring system in each is essentially planar, with maximum deviations of 0.025 (16) and 0.0171 (16) Å. The dihedral angles between quinazoline ring systems and the phenyl rings are 88.25 (8) and 85.28 (16)° in the two independent mol-ecules. In the crystal, alternating independent mol-ecules are linked by N-H⋯N hydrogen bonds, forming chains along [001].

Related literature

For the biological activity of some quinazoline and related derivatives, see: Deng & Mani (2006 ▶); Lee et al. (1995 ▶); Lopez et al. (2011 ▶); Mohamed et al. (2011 ▶); Wynne et al. (2009 ▶); Yoshida & Taguchi (1992 ▶); Zhang et al. (2009 ▶); Zhou et al. (2011 ▶).

Experimental

Crystal data

C15H12ClN3

M = 269.73

Triclinic,

a = 9.4018 (1) Å

b = 13.0108 (1) Å

c = 13.3035 (1) Å

α = 113.968 (1)°

β = 105.377 (1)°

γ = 100.213 (1)°

V = 1356.69 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.35 × 0.26 × 0.10 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.911, T max = 0.974

22349 measured reflections

6531 independent reflections

5274 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 15 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.086

S = 1.13

6531 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814006746/lh5690sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006746/lh5690Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006746/lh5690Isup3.cml

CCDC reference: 993912

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12ClN3	Z = 4
Mr = 269.73	F(000) = 560
Triclinic, P1	Dx = 1.321 Mg m−3
a = 9.4018 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0108 (1) Å	Cell parameters from 407 reflections
c = 13.3035 (1) Å	θ = 1.5–30°
α = 113.968 (1)°	µ = 0.27 mm−1
β = 105.377 (1)°	T = 296 K
γ = 100.213 (1)°	Block, colourless
V = 1356.69 (2) Å3	0.35 × 0.26 × 0.10 mm

Bruker Kappa APEXII diffractometer	5274 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28.0°, θmin = 2.4°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −17→17
Tmin = 0.911, Tmax = 0.974	l = −17→17
22349 measured reflections	3 standard reflections every 15 min
6531 independent reflections	intensity decay: none

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0141P)2 + 0.4615P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.33 e Å−3
6531 reflections	Δρmin = −0.49 e Å−3
344 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0041 (6)

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.

	x	y	z	Uiso*/Ueq
Cl1A	0.80906 (7)	0.05252 (4)	0.09218 (4)	0.07177 (16)
N1A	0.75236 (15)	0.23972 (11)	0.09405 (10)	0.0431 (3)
N2A	0.81249 (15)	0.11531 (11)	−0.06785 (10)	0.0437 (3)
N3A	0.81842 (15)	0.15522 (12)	−0.21892 (11)	0.0461 (3)
H3AA	0.8049	0.1991	−0.2522	0.055*
C1A	0.78763 (18)	0.14847 (13)	0.03282 (13)	0.0432 (3)
C2A	0.74116 (16)	0.31670 (12)	0.04724 (12)	0.0381 (3)
C3A	0.76545 (16)	0.29524 (13)	−0.05817 (12)	0.0373 (3)
C4A	0.79930 (16)	0.18703 (13)	−0.11613 (12)	0.0375 (3)
C5A	0.7048 (2)	0.41884 (15)	0.10729 (14)	0.0515 (4)
H5AA	0.6880	0.4334	0.1769	0.062*
C6A	0.6941 (2)	0.49701 (16)	0.06391 (16)	0.0617 (5)
H6AA	0.6697	0.5645	0.1042	0.074*
C7A	0.7193 (2)	0.47677 (16)	−0.04001 (17)	0.0648 (5)
H7AA	0.7121	0.5309	−0.0685	0.078*
C8A	0.7548 (2)	0.37788 (15)	−0.10035 (15)	0.0532 (4)
H8AA	0.7718	0.3651	−0.1696	0.064*
C9A	0.86081 (18)	0.05090 (14)	−0.27836 (13)	0.0485 (4)
H9AA	0.8007	0.0127	−0.3629	0.058*
H9AB	0.8337	−0.0050	−0.2502	0.058*
C10A	1.03177 (17)	0.07992 (12)	−0.25780 (12)	0.0387 (3)
C11A	1.14458 (19)	0.16829 (14)	−0.15033 (14)	0.0472 (4)
H11A	1.1148	0.2127	−0.0895	0.057*
C12A	1.3005 (2)	0.19105 (16)	−0.13271 (17)	0.0594 (4)
H12A	1.3753	0.2502	−0.0600	0.071*
C13A	1.3458 (2)	0.12649 (18)	−0.2225 (2)	0.0670 (5)
H13A	1.4510	0.1419	−0.2106	0.080*
C14A	1.2353 (2)	0.03958 (16)	−0.32935 (19)	0.0638 (5)
H14A	1.2656	−0.0037	−0.3903	0.077*
C15A	1.0797 (2)	0.01593 (14)	−0.34694 (15)	0.0499 (4)
H15A	1.0057	−0.0438	−0.4197	0.060*
Cl1B	0.49469 (5)	0.17163 (4)	0.57865 (4)	0.06102 (13)
N1B	0.78003 (14)	0.23433 (11)	0.59600 (10)	0.0413 (3)
N2B	0.58069 (14)	0.20758 (11)	0.42357 (10)	0.0416 (3)
N3B	0.63353 (14)	0.23214 (12)	0.27581 (10)	0.0442 (3)
H3BA	0.7001	0.2522	0.2480	0.053*
C1B	0.63823 (17)	0.20955 (13)	0.52713 (13)	0.0402 (3)
C2B	0.89177 (16)	0.26517 (12)	0.55393 (12)	0.0378 (3)
C3B	0.85120 (16)	0.26871 (12)	0.44613 (12)	0.0369 (3)
C4B	0.68648 (16)	0.23599 (12)	0.38078 (12)	0.0375 (3)
C5B	1.04922 (18)	0.29186 (14)	0.62032 (14)	0.0487 (4)
H5BA	1.0771	0.2897	0.6918	0.058*
C6B	1.16159 (19)	0.32102 (16)	0.58031 (15)	0.0569 (4)
H6BA	1.2657	0.3381	0.6246	0.068*
C7B	1.12207 (19)	0.32550 (17)	0.47386 (16)	0.0593 (4)
H7BA	1.1997	0.3457	0.4477	0.071*
C8B	0.96948 (18)	0.30032 (15)	0.40786 (14)	0.0497 (4)
H8BA	0.9438	0.3041	0.3372	0.060*
C9B	0.46910 (17)	0.19581 (14)	0.20594 (13)	0.0460 (3)
H9BA	0.4136	0.1313	0.2143	0.055*
H9BB	0.4553	0.1652	0.1230	0.055*
C10B	0.39638 (16)	0.29301 (13)	0.23906 (12)	0.0404 (3)
C11B	0.48004 (19)	0.40835 (15)	0.32662 (15)	0.0537 (4)
H11B	0.5860	0.4282	0.3680	0.064*
C12B	0.4087 (2)	0.49486 (16)	0.35374 (17)	0.0625 (5)
H12B	0.4667	0.5721	0.4134	0.075*
C13B	0.2534 (2)	0.46736 (18)	0.29325 (18)	0.0626 (5)
H13B	0.2054	0.5255	0.3112	0.075*
C14B	0.1692 (2)	0.35318 (19)	0.20577 (19)	0.0679 (5)
H14B	0.0635	0.3341	0.1641	0.081*
C15B	0.23929 (19)	0.26642 (16)	0.17885 (15)	0.0558 (4)
H15B	0.1803	0.1892	0.1196	0.067*

	U11	U22	U33	U12	U13	U23
Cl1A	0.1269 (4)	0.0514 (3)	0.0519 (3)	0.0322 (3)	0.0343 (3)	0.0364 (2)
N1A	0.0559 (7)	0.0427 (7)	0.0340 (6)	0.0137 (6)	0.0193 (6)	0.0209 (5)
N2A	0.0582 (8)	0.0414 (7)	0.0353 (6)	0.0188 (6)	0.0178 (6)	0.0205 (5)
N3A	0.0578 (8)	0.0574 (8)	0.0391 (7)	0.0293 (6)	0.0251 (6)	0.0288 (6)
C1A	0.0559 (9)	0.0386 (8)	0.0358 (7)	0.0107 (7)	0.0141 (7)	0.0222 (6)
C2A	0.0399 (7)	0.0396 (7)	0.0334 (7)	0.0112 (6)	0.0126 (6)	0.0177 (6)
C3A	0.0387 (7)	0.0416 (8)	0.0347 (7)	0.0133 (6)	0.0131 (6)	0.0214 (6)
C4A	0.0373 (7)	0.0440 (8)	0.0330 (7)	0.0132 (6)	0.0127 (6)	0.0202 (6)
C5A	0.0650 (10)	0.0511 (9)	0.0413 (8)	0.0237 (8)	0.0250 (8)	0.0198 (7)
C6A	0.0832 (13)	0.0488 (10)	0.0561 (10)	0.0336 (9)	0.0268 (9)	0.0224 (8)
C7A	0.0954 (14)	0.0545 (10)	0.0622 (11)	0.0365 (10)	0.0306 (10)	0.0382 (9)
C8A	0.0746 (11)	0.0542 (10)	0.0464 (9)	0.0274 (9)	0.0275 (8)	0.0325 (8)
C9A	0.0537 (9)	0.0500 (9)	0.0367 (8)	0.0168 (7)	0.0194 (7)	0.0144 (7)
C10A	0.0517 (8)	0.0360 (7)	0.0358 (7)	0.0169 (6)	0.0196 (6)	0.0207 (6)
C11A	0.0579 (9)	0.0452 (9)	0.0392 (8)	0.0178 (7)	0.0177 (7)	0.0205 (7)
C12A	0.0550 (10)	0.0531 (10)	0.0601 (11)	0.0078 (8)	0.0105 (8)	0.0289 (9)
C13A	0.0535 (10)	0.0669 (12)	0.0961 (15)	0.0193 (9)	0.0366 (11)	0.0475 (12)
C14A	0.0730 (12)	0.0543 (10)	0.0812 (13)	0.0246 (9)	0.0521 (11)	0.0317 (10)
C15A	0.0645 (10)	0.0394 (8)	0.0473 (9)	0.0147 (7)	0.0300 (8)	0.0172 (7)
Cl1B	0.0539 (2)	0.0861 (3)	0.0579 (3)	0.0173 (2)	0.0323 (2)	0.0430 (2)
N1B	0.0468 (7)	0.0482 (7)	0.0335 (6)	0.0145 (6)	0.0176 (5)	0.0224 (6)
N2B	0.0424 (6)	0.0507 (7)	0.0378 (6)	0.0165 (6)	0.0186 (5)	0.0238 (6)
N3B	0.0442 (7)	0.0593 (8)	0.0366 (6)	0.0178 (6)	0.0175 (5)	0.0279 (6)
C1B	0.0465 (8)	0.0433 (8)	0.0391 (7)	0.0146 (6)	0.0240 (6)	0.0222 (6)
C2B	0.0445 (8)	0.0363 (7)	0.0333 (7)	0.0129 (6)	0.0161 (6)	0.0164 (6)
C3B	0.0410 (7)	0.0376 (7)	0.0328 (7)	0.0117 (6)	0.0158 (6)	0.0167 (6)
C4B	0.0455 (8)	0.0381 (7)	0.0334 (7)	0.0160 (6)	0.0176 (6)	0.0183 (6)
C5B	0.0473 (8)	0.0550 (9)	0.0383 (8)	0.0116 (7)	0.0094 (7)	0.0235 (7)
C6B	0.0391 (8)	0.0670 (11)	0.0533 (10)	0.0079 (8)	0.0096 (7)	0.0271 (9)
C7B	0.0439 (9)	0.0745 (12)	0.0571 (10)	0.0067 (8)	0.0222 (8)	0.0324 (9)
C8B	0.0483 (9)	0.0615 (10)	0.0413 (8)	0.0104 (7)	0.0189 (7)	0.0280 (8)
C9B	0.0469 (8)	0.0510 (9)	0.0336 (7)	0.0127 (7)	0.0099 (6)	0.0188 (7)
C10B	0.0418 (7)	0.0489 (8)	0.0320 (7)	0.0108 (6)	0.0131 (6)	0.0228 (6)
C11B	0.0460 (9)	0.0503 (9)	0.0505 (9)	0.0099 (7)	0.0080 (7)	0.0198 (8)
C12B	0.0681 (12)	0.0483 (10)	0.0621 (11)	0.0160 (9)	0.0205 (9)	0.0219 (9)
C13B	0.0703 (12)	0.0638 (12)	0.0747 (12)	0.0340 (10)	0.0371 (10)	0.0409 (10)
C14B	0.0452 (9)	0.0793 (14)	0.0774 (13)	0.0228 (9)	0.0166 (9)	0.0387 (11)
C15B	0.0447 (9)	0.0570 (10)	0.0501 (9)	0.0092 (7)	0.0088 (7)	0.0199 (8)

Cl1A—C1A	1.7403 (14)	Cl1B—C1B	1.7503 (14)
N1A—C1A	1.2962 (19)	N1B—C1B	1.2964 (19)
N1A—C2A	1.3826 (18)	N1B—C2B	1.3866 (17)
N2A—C1A	1.3291 (18)	N2B—C1B	1.3275 (18)
N2A—C4A	1.3359 (18)	N2B—C4B	1.3383 (17)
N3A—C4A	1.3305 (17)	N3B—C4B	1.3289 (17)
N3A—C9A	1.4537 (19)	N3B—C9B	1.4489 (18)
N3A—H3AA	0.8600	N3B—H3BA	0.8600
C2A—C5A	1.401 (2)	C2B—C5B	1.403 (2)
C2A—C3A	1.4040 (18)	C2B—C3B	1.4051 (19)
C3A—C8A	1.407 (2)	C3B—C8B	1.4047 (19)
C3A—C4A	1.444 (2)	C3B—C4B	1.4446 (19)
C5A—C6A	1.364 (2)	C5B—C6B	1.365 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.392 (3)	C6B—C7B	1.394 (2)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C8A	1.366 (2)	C7B—C8B	1.367 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.506 (2)	C9B—C10B	1.508 (2)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—C15A	1.384 (2)	C10B—C11B	1.379 (2)
C10A—C11A	1.385 (2)	C10B—C15B	1.382 (2)
C11A—C12A	1.378 (2)	C11B—C12B	1.383 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.377 (3)	C12B—C13B	1.365 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.368 (3)	C13B—C14B	1.370 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.375 (2)	C14B—C15B	1.378 (3)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C1A—N1A—C2A	114.20 (12)	C1B—N1B—C2B	113.92 (12)
C1A—N2A—C4A	115.75 (12)	C1B—N2B—C4B	115.30 (12)
C4A—N3A—C9A	124.03 (13)	C4B—N3B—C9B	123.18 (12)
C4A—N3A—H3AA	118.0	C4B—N3B—H3BA	118.4
C9A—N3A—H3AA	118.0	C9B—N3B—H3BA	118.4
N1A—C1A—N2A	131.20 (13)	N1B—C1B—N2B	131.77 (13)
N1A—C1A—Cl1A	115.28 (11)	N1B—C1B—Cl1B	114.95 (10)
N2A—C1A—Cl1A	113.52 (11)	N2B—C1B—Cl1B	113.29 (11)
N1A—C2A—C5A	118.76 (13)	N1B—C2B—C5B	118.87 (13)
N1A—C2A—C3A	121.78 (13)	N1B—C2B—C3B	121.78 (13)
C5A—C2A—C3A	119.46 (13)	C5B—C2B—C3B	119.35 (13)
C2A—C3A—C8A	119.10 (13)	C8B—C3B—C2B	119.24 (13)
C2A—C3A—C4A	116.21 (12)	C8B—C3B—C4B	124.64 (13)
C8A—C3A—C4A	124.69 (13)	C2B—C3B—C4B	116.11 (12)
N3A—C4A—N2A	117.73 (13)	N3B—C4B—N2B	117.24 (13)
N3A—C4A—C3A	121.47 (13)	N3B—C4B—C3B	121.66 (12)
N2A—C4A—C3A	120.80 (12)	N2B—C4B—C3B	121.10 (12)
C6A—C5A—C2A	120.19 (15)	C6B—C5B—C2B	120.14 (14)
C6A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.9
C2A—C5A—H5AA	119.9	C2B—C5B—H5BA	119.9
C5A—C6A—C7A	120.63 (16)	C5B—C6B—C7B	120.74 (15)
C5A—C6A—H6AA	119.7	C5B—C6B—H6BA	119.6
C7A—C6A—H6AA	119.7	C7B—C6B—H6BA	119.6
C8A—C7A—C6A	120.38 (16)	C8B—C7B—C6B	120.19 (15)
C8A—C7A—H7AA	119.8	C8B—C7B—H7BA	119.9
C6A—C7A—H7AA	119.8	C6B—C7B—H7BA	119.9
C7A—C8A—C3A	120.23 (15)	C7B—C8B—C3B	120.34 (14)
C7A—C8A—H8AA	119.9	C7B—C8B—H8BA	119.8
C3A—C8A—H8AA	119.9	C3B—C8B—H8BA	119.8
N3A—C9A—C10A	112.90 (13)	N3B—C9B—C10B	114.71 (12)
N3A—C9A—H9AA	109.0	N3B—C9B—H9BA	108.6
C10A—C9A—H9AA	109.0	C10B—C9B—H9BA	108.6
N3A—C9A—H9AB	109.0	N3B—C9B—H9BB	108.6
C10A—C9A—H9AB	109.0	C10B—C9B—H9BB	108.6
H9AA—C9A—H9AB	107.8	H9BA—C9B—H9BB	107.6
C15A—C10A—C11A	118.33 (14)	C11B—C10B—C15B	118.09 (15)
C15A—C10A—C9A	119.91 (14)	C11B—C10B—C9B	122.94 (14)
C11A—C10A—C9A	121.75 (13)	C15B—C10B—C9B	118.97 (14)
C12A—C11A—C10A	120.64 (15)	C10B—C11B—C12B	120.99 (16)
C12A—C11A—H11A	119.7	C10B—C11B—H11B	119.5
C10A—C11A—H11A	119.7	C12B—C11B—H11B	119.5
C13A—C12A—C11A	120.16 (17)	C13B—C12B—C11B	120.26 (17)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.9
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.9
C14A—C13A—C12A	119.70 (17)	C12B—C13B—C14B	119.29 (17)
C14A—C13A—H13A	120.1	C12B—C13B—H13B	120.4
C12A—C13A—H13A	120.1	C14B—C13B—H13B	120.4
C13A—C14A—C15A	120.30 (17)	C13B—C14B—C15B	120.74 (17)
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.6
C15A—C14A—H14A	119.8	C15B—C14B—H14B	119.6
C14A—C15A—C10A	120.86 (16)	C14B—C15B—C10B	120.61 (17)
C14A—C15A—H15A	119.6	C14B—C15B—H15B	119.7
C10A—C15A—H15A	119.6	C10B—C15B—H15B	119.7
C2A—N1A—C1A—N2A	−1.2 (2)	C2B—N1B—C1B—N2B	0.5 (2)
C2A—N1A—C1A—Cl1A	177.92 (10)	C2B—N1B—C1B—Cl1B	−179.43 (10)
C4A—N2A—C1A—N1A	−0.1 (3)	C4B—N2B—C1B—N1B	0.1 (2)
C4A—N2A—C1A—Cl1A	−179.20 (11)	C4B—N2B—C1B—Cl1B	−179.97 (10)
C1A—N1A—C2A—C5A	−179.46 (14)	C1B—N1B—C2B—C5B	−178.94 (14)
C1A—N1A—C2A—C3A	0.4 (2)	C1B—N1B—C2B—C3B	0.2 (2)
N1A—C2A—C3A—C8A	−179.03 (14)	N1B—C2B—C3B—C8B	−179.85 (14)
C5A—C2A—C3A—C8A	0.8 (2)	C5B—C2B—C3B—C8B	−0.8 (2)
N1A—C2A—C3A—C4A	1.3 (2)	N1B—C2B—C3B—C4B	−1.2 (2)
C5A—C2A—C3A—C4A	−178.80 (13)	C5B—C2B—C3B—C4B	177.84 (13)
C9A—N3A—C4A—N2A	−3.4 (2)	C9B—N3B—C4B—N2B	−1.8 (2)
C9A—N3A—C4A—C3A	176.58 (13)	C9B—N3B—C4B—C3B	177.81 (13)
C1A—N2A—C4A—N3A	−177.93 (13)	C1B—N2B—C4B—N3B	178.31 (13)
C1A—N2A—C4A—C3A	2.1 (2)	C1B—N2B—C4B—C3B	−1.3 (2)
C2A—C3A—C4A—N3A	177.36 (13)	C8B—C3B—C4B—N3B	0.8 (2)
C8A—C3A—C4A—N3A	−2.3 (2)	C2B—C3B—C4B—N3B	−177.75 (13)
C2A—C3A—C4A—N2A	−2.6 (2)	C8B—C3B—C4B—N2B	−179.62 (14)
C8A—C3A—C4A—N2A	177.74 (15)	C2B—C3B—C4B—N2B	1.9 (2)
N1A—C2A—C5A—C6A	179.50 (15)	N1B—C2B—C5B—C6B	179.16 (15)
C3A—C2A—C5A—C6A	−0.4 (2)	C3B—C2B—C5B—C6B	0.0 (2)
C2A—C5A—C6A—C7A	−0.2 (3)	C2B—C5B—C6B—C7B	0.4 (3)
C5A—C6A—C7A—C8A	0.2 (3)	C5B—C6B—C7B—C8B	−0.2 (3)
C6A—C7A—C8A—C3A	0.2 (3)	C6B—C7B—C8B—C3B	−0.6 (3)
C2A—C3A—C8A—C7A	−0.8 (2)	C2B—C3B—C8B—C7B	1.0 (2)
C4A—C3A—C8A—C7A	178.83 (16)	C4B—C3B—C8B—C7B	−177.45 (16)
C4A—N3A—C9A—C10A	−99.54 (17)	C4B—N3B—C9B—C10B	83.98 (18)
N3A—C9A—C10A—C15A	−145.39 (14)	N3B—C9B—C10B—C11B	1.7 (2)
N3A—C9A—C10A—C11A	35.9 (2)	N3B—C9B—C10B—C15B	−178.82 (14)
C15A—C10A—C11A—C12A	−0.5 (2)	C15B—C10B—C11B—C12B	0.2 (2)
C9A—C10A—C11A—C12A	178.29 (15)	C9B—C10B—C11B—C12B	179.71 (15)
C10A—C11A—C12A—C13A	0.5 (3)	C10B—C11B—C12B—C13B	−0.4 (3)
C11A—C12A—C13A—C14A	0.0 (3)	C11B—C12B—C13B—C14B	0.2 (3)
C12A—C13A—C14A—C15A	−0.5 (3)	C12B—C13B—C14B—C15B	0.2 (3)
C13A—C14A—C15A—C10A	0.6 (3)	C13B—C14B—C15B—C10B	−0.4 (3)
C11A—C10A—C15A—C14A	−0.1 (2)	C11B—C10B—C15B—C14B	0.2 (2)
C9A—C10A—C15A—C14A	−178.87 (15)	C9B—C10B—C15B—C14B	−179.30 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3AA···N1Bi	0.86	2.21	2.9954 (17)	152
N3B—H3BA···N1A	0.86	2.18	2.9482 (16)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H3AA⋯N1B i	0.86	2.21	2.9954 (17)	152
N3B—H3BA⋯N1A	0.86	2.18	2.9482 (16)	149

Symmetry code: (i) .