6-Chloro-N(4),N(4)-dimethyl-pyrimidine-2,4-diamine.

The asymmetric unit of the title compound, C(6)H(9)ClN(4), contains four independent mol-ecules (A, B, C and D). Their main difference is the torsion angles, ranging from 1.6 (5) to 5.9 (5)°, between the methyl group and the pyrimidine plane. A pair of inter-molecular N-H⋯N hydrogen bonds link mol-ecules A and C into a twisted dimer with a dihedral angle of 32.9 (1)° between the two pyrimidine rings, creating an R(2) (2)(8) motif. In the packing, each two mol-ecules of B, C and D form centrosymmetric dimers through two inter-molecular N-H⋯N hydrogen bonds, locally creating R(2) (2)(8) motifs. The dimers of C and D are alternately bridged by A into an infinite zigzag strip, locally creating two different R(2) (2)(8) motifs with dihedral angles of 32.9 (1) and 63.4 (1)° between the pyrimidine rings. Finally, these strips together with the dimers of B associate into a complicated three-dimensional framework.

Related literature

For background to pyrimidine derivatives, see: Ligthart et al. (2005 ▶); Rabie et al. (2007 ▶); Goswami et al.(2008 ▶); Sherrington & Taskinen (2001 ▶). For similar structures, see: Cetina et al. (2005 ▶); Fun et al. (2006 ▶); Li et al. (2008 ▶); Ebenezer & Muthiah (2010 ▶); Cheng et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H9ClN4

M = 172.62

Triclinic,

a = 7.9438 (19) Å

b = 14.225 (3) Å

c = 14.895 (3) Å

α = 100.114 (3)°

β = 94.421 (4)°

γ = 100.524 (4)°

V = 1618.7 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.21 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.919, T max = 0.937

8239 measured reflections

5619 independent reflections

3769 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.136

S = 0.97

5619 reflections

405 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013517/zq2159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013517/zq2159Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013517/zq2159Isup3.cml

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

C6H9ClN4	Z = 8
Mr = 172.62	F(000) = 720
Triclinic, P1	Dx = 1.417 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9438 (19) Å	Cell parameters from 2311 reflections
b = 14.225 (3) Å	θ = 2.6–27.7°
c = 14.895 (3) Å	µ = 0.41 mm−1
α = 100.114 (3)°	T = 298 K
β = 94.421 (4)°	Block, colourless
γ = 100.524 (4)°	0.21 × 0.18 × 0.16 mm
V = 1618.7 (7) Å3

Bruker SMART CCD area-detector diffractometer	5619 independent reflections
Radiation source: fine-focus sealed tube	3769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→8
Tmin = 0.919, Tmax = 0.937	k = −16→16
8239 measured reflections	l = −17→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0681P)2] where P = (Fo2 + 2Fc2)/3
5619 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
N1	0.3407 (3)	0.34115 (18)	0.54662 (16)	0.0383 (6)
N2	0.4648 (3)	0.47960 (18)	0.66542 (16)	0.0369 (6)
N3	0.5150 (4)	0.32771 (19)	0.67110 (18)	0.0534 (8)
N4	0.1803 (4)	0.3573 (2)	0.41724 (17)	0.0498 (8)
N5	0.3131 (3)	0.56029 (17)	0.00737 (15)	0.0377 (6)
N6	0.2031 (3)	0.57494 (17)	0.15383 (16)	0.0356 (6)
N7	0.4281 (4)	0.49791 (19)	0.12364 (16)	0.0469 (8)
N8	−0.0361 (4)	0.64285 (19)	0.18002 (18)	0.0451 (7)
N9	0.4193 (3)	0.08990 (18)	0.62696 (16)	0.0379 (6)
N10	0.1931 (3)	−0.03793 (18)	0.54295 (16)	0.0390 (7)
N11	0.1596 (4)	0.12009 (19)	0.5723 (2)	0.0542 (8)
N12	0.6743 (4)	0.0572 (2)	0.68555 (18)	0.0478 (7)
N13	0.3235 (4)	0.9764 (2)	0.83692 (19)	0.0511 (8)
N14	0.5994 (4)	1.03959 (18)	0.90517 (17)	0.0405 (7)
N15	0.8008 (3)	0.93718 (19)	0.93227 (17)	0.0412 (7)
N16	0.8765 (4)	1.10315 (19)	0.9711 (2)	0.0567 (8)
C1	0.2689 (4)	0.3996 (2)	0.4992 (2)	0.0387 (8)
C2	0.2883 (4)	0.4998 (2)	0.5353 (2)	0.0405 (8)
H2	0.2382	0.5412	0.5047	0.049*
C3	0.3852 (4)	0.5320 (2)	0.6179 (2)	0.0370 (8)
C4	0.4379 (4)	0.3849 (2)	0.6250 (2)	0.0399 (8)
C5	0.1705 (5)	0.2558 (3)	0.3791 (2)	0.0619 (11)
H5A	0.2531	0.2309	0.4139	0.093*
H5B	0.1951	0.2490	0.3164	0.093*
H5C	0.0568	0.2198	0.3815	0.093*
C6	0.1034 (5)	0.4146 (3)	0.3586 (2)	0.0667 (11)
H6A	0.0397	0.4559	0.3942	0.100*
H6B	0.0272	0.3715	0.3092	0.100*
H6C	0.1929	0.4541	0.3340	0.100*
C7	0.0773 (4)	0.6171 (2)	0.1222 (2)	0.0362 (8)
C8	−0.1760 (5)	0.6879 (3)	0.1505 (3)	0.0643 (11)
H8A	−0.1297	0.7441	0.1262	0.096*
H8B	−0.2361	0.7072	0.2020	0.096*
H8C	−0.2544	0.6420	0.1039	0.096*
C9	−0.0343 (5)	0.6179 (3)	0.2706 (2)	0.0570 (10)
H9A	−0.1284	0.5649	0.2705	0.086*
H9B	−0.0458	0.6735	0.3150	0.086*
H9C	0.0725	0.5990	0.2861	0.086*
C10	0.0687 (4)	0.6347 (2)	0.0317 (2)	0.0376 (8)
H10	−0.0150	0.6648	0.0084	0.045*
C11	0.1901 (4)	0.6050 (2)	−0.01859 (19)	0.0363 (8)
C12	0.3096 (4)	0.5455 (2)	0.09442 (19)	0.0348 (7)
C13	0.7969 (5)	−0.0067 (3)	0.6925 (2)	0.0623 (11)
H13A	0.7474	−0.0597	0.7204	0.093*
H13B	0.9006	0.0295	0.7293	0.093*
H13C	0.8232	−0.0321	0.6322	0.093*
C14	0.7279 (5)	0.1570 (2)	0.7337 (3)	0.0610 (11)
H14A	0.7736	0.1970	0.6921	0.092*
H14B	0.8149	0.1607	0.7833	0.092*
H14C	0.6306	0.1797	0.7577	0.092*
C15	0.5186 (4)	0.0239 (2)	0.63617 (19)	0.0375 (8)
C16	0.4614 (4)	−0.0744 (2)	0.5956 (2)	0.0418 (8)
H16	0.5303	−0.1203	0.5987	0.050*
C17	0.2997 (4)	−0.0987 (2)	0.55161 (19)	0.0367 (8)
C18	0.2619 (4)	0.0556 (2)	0.5810 (2)	0.0380 (8)
C19	0.1863 (5)	0.8969 (3)	0.7904 (3)	0.0694 (12)
H19A	0.2290	0.8584	0.7410	0.104*
H19B	0.0928	0.9228	0.7663	0.104*
H19C	0.1462	0.8569	0.8330	0.104*
C20	0.2873 (5)	1.0738 (3)	0.8461 (2)	0.0594 (11)
H20A	0.3797	1.1194	0.8848	0.089*
H20B	0.1816	1.0755	0.8730	0.089*
H20C	0.2765	1.0909	0.7867	0.089*
C21	0.4788 (4)	0.9608 (2)	0.8677 (2)	0.0394 (8)
C22	0.5135 (4)	0.8663 (2)	0.8614 (2)	0.0447 (9)
H22	0.4315	0.8106	0.8359	0.054*
C23	0.6750 (5)	0.8624 (2)	0.8952 (2)	0.0419 (8)
C24	0.7528 (4)	1.0241 (2)	0.9355 (2)	0.0396 (8)
Cl1	0.41068 (13)	0.65460 (6)	0.66924 (6)	0.0559 (3)
Cl2	0.72990 (15)	0.74846 (7)	0.89197 (7)	0.0725 (3)
Cl3	0.21621 (13)	−0.21962 (6)	0.49962 (6)	0.0594 (3)
Cl4	0.19291 (13)	0.62621 (7)	−0.13080 (5)	0.0581 (3)
H7A	0.4312	0.4882	0.1794	0.070*
H11B	0.2061	0.1818	0.5803	0.070*
H16A	0.8516	1.1614	0.9822	0.070*
H3A	0.4991	0.2653	0.6522	0.070*
H7B	0.5017	0.4822	0.0852	0.070*
H16B	0.9661	1.0935	1.0027	0.070*
H3B	0.5805	0.3546	0.7235	0.070*
H11A	0.0579	0.1009	0.5408	0.070*

	U11	U22	U33	U12	U13	U23
N1	0.0343 (17)	0.0405 (16)	0.0382 (14)	0.0061 (13)	−0.0005 (12)	0.0055 (12)
N2	0.0337 (17)	0.0400 (16)	0.0369 (14)	0.0079 (13)	0.0031 (12)	0.0067 (12)
N3	0.066 (2)	0.0450 (17)	0.0496 (17)	0.0224 (16)	−0.0095 (15)	0.0045 (13)
N4	0.047 (2)	0.060 (2)	0.0405 (16)	0.0082 (15)	−0.0063 (14)	0.0101 (14)
N5	0.0362 (17)	0.0406 (16)	0.0368 (15)	0.0086 (13)	0.0070 (12)	0.0070 (11)
N6	0.0336 (17)	0.0365 (15)	0.0388 (14)	0.0103 (13)	0.0078 (12)	0.0078 (11)
N7	0.050 (2)	0.0593 (19)	0.0398 (15)	0.0284 (16)	0.0106 (13)	0.0122 (13)
N8	0.0385 (18)	0.0476 (17)	0.0540 (17)	0.0158 (14)	0.0164 (14)	0.0101 (13)
N9	0.0298 (16)	0.0432 (16)	0.0411 (15)	0.0069 (13)	−0.0009 (12)	0.0115 (12)
N10	0.0314 (17)	0.0422 (17)	0.0415 (15)	0.0040 (14)	−0.0016 (12)	0.0093 (12)
N11	0.0368 (19)	0.0418 (17)	0.081 (2)	0.0086 (14)	−0.0111 (16)	0.0110 (14)
N12	0.0370 (18)	0.0517 (19)	0.0523 (17)	0.0066 (15)	−0.0087 (14)	0.0122 (14)
N13	0.0315 (18)	0.059 (2)	0.0599 (18)	0.0097 (15)	−0.0050 (14)	0.0063 (14)
N14	0.0359 (18)	0.0409 (16)	0.0439 (15)	0.0071 (14)	0.0011 (13)	0.0086 (12)
N15	0.0354 (17)	0.0395 (17)	0.0452 (15)	0.0040 (14)	−0.0049 (13)	0.0062 (12)
N16	0.048 (2)	0.0376 (17)	0.077 (2)	0.0010 (15)	−0.0156 (16)	0.0083 (14)
C1	0.0256 (19)	0.049 (2)	0.0412 (18)	0.0038 (16)	0.0070 (15)	0.0107 (15)
C2	0.033 (2)	0.050 (2)	0.0437 (19)	0.0134 (16)	0.0066 (15)	0.0154 (15)
C3	0.032 (2)	0.0403 (19)	0.0410 (18)	0.0072 (16)	0.0159 (15)	0.0094 (14)
C4	0.033 (2)	0.046 (2)	0.0418 (18)	0.0081 (16)	0.0063 (15)	0.0116 (16)
C5	0.061 (3)	0.060 (3)	0.050 (2)	−0.008 (2)	−0.0051 (19)	−0.0023 (17)
C6	0.054 (3)	0.095 (3)	0.051 (2)	0.019 (2)	−0.0105 (19)	0.017 (2)
C7	0.034 (2)	0.0230 (17)	0.0479 (18)	0.0003 (15)	0.0042 (15)	0.0028 (13)
C8	0.047 (3)	0.069 (3)	0.086 (3)	0.029 (2)	0.020 (2)	0.015 (2)
C9	0.057 (3)	0.059 (2)	0.058 (2)	0.010 (2)	0.0266 (19)	0.0089 (17)
C10	0.035 (2)	0.0297 (18)	0.0488 (19)	0.0062 (15)	0.0008 (16)	0.0107 (14)
C11	0.039 (2)	0.0290 (17)	0.0374 (17)	−0.0008 (15)	0.0005 (15)	0.0074 (13)
C12	0.033 (2)	0.0321 (18)	0.0383 (17)	0.0067 (15)	0.0053 (15)	0.0040 (13)
C13	0.041 (2)	0.076 (3)	0.071 (3)	0.018 (2)	−0.009 (2)	0.017 (2)
C14	0.050 (3)	0.053 (2)	0.073 (3)	−0.0062 (19)	−0.019 (2)	0.0236 (19)
C15	0.031 (2)	0.047 (2)	0.0357 (17)	0.0060 (16)	0.0044 (15)	0.0143 (14)
C16	0.033 (2)	0.048 (2)	0.0485 (19)	0.0157 (17)	0.0056 (16)	0.0128 (16)
C17	0.034 (2)	0.0422 (19)	0.0354 (17)	0.0076 (16)	0.0033 (15)	0.0108 (14)
C18	0.030 (2)	0.046 (2)	0.0405 (17)	0.0097 (17)	0.0055 (15)	0.0134 (15)
C19	0.038 (2)	0.088 (3)	0.076 (3)	0.006 (2)	−0.010 (2)	0.014 (2)
C20	0.052 (3)	0.074 (3)	0.061 (2)	0.032 (2)	0.0055 (19)	0.0148 (19)
C21	0.035 (2)	0.043 (2)	0.0380 (17)	0.0033 (17)	0.0050 (15)	0.0064 (14)
C22	0.039 (2)	0.042 (2)	0.0471 (19)	−0.0002 (17)	−0.0058 (16)	0.0035 (15)
C23	0.046 (2)	0.037 (2)	0.0430 (18)	0.0104 (17)	−0.0022 (17)	0.0085 (14)
C24	0.038 (2)	0.039 (2)	0.0386 (17)	0.0002 (17)	0.0019 (15)	0.0080 (14)
Cl1	0.0686 (7)	0.0406 (5)	0.0582 (5)	0.0122 (5)	0.0097 (5)	0.0062 (4)
Cl2	0.0785 (8)	0.0406 (6)	0.0913 (7)	0.0163 (5)	−0.0270 (6)	0.0051 (5)
Cl3	0.0610 (7)	0.0407 (5)	0.0700 (6)	0.0063 (5)	−0.0074 (5)	0.0037 (4)
Cl4	0.0674 (7)	0.0670 (6)	0.0436 (5)	0.0108 (5)	0.0059 (4)	0.0233 (4)

N1—C4	1.333 (4)	C1—C2	1.409 (4)
N1—C1	1.353 (4)	C2—C3	1.357 (4)
N2—C3	1.321 (4)	C2—H2	0.9300
N2—C4	1.347 (4)	C3—Cl1	1.746 (3)
N3—C4	1.350 (4)	C5—H5A	0.9600
N3—H3A	0.8649	C5—H5B	0.9600
N3—H3B	0.8870	C5—H5C	0.9600
N4—C1	1.343 (4)	C6—H6A	0.9600
N4—C5	1.441 (4)	C6—H6B	0.9600
N4—C6	1.467 (4)	C6—H6C	0.9600
N5—C11	1.329 (4)	C7—C10	1.411 (4)
N5—C12	1.351 (3)	C8—H8A	0.9600
N6—C12	1.338 (4)	C8—H8B	0.9600
N6—C7	1.351 (4)	C8—H8C	0.9600
N7—C12	1.344 (4)	C9—H9A	0.9600
N7—H7A	0.8654	C9—H9B	0.9600
N7—H7B	0.8789	C9—H9C	0.9600
N8—C7	1.348 (4)	C10—C11	1.349 (4)
N8—C9	1.453 (4)	C10—H10	0.9300
N8—C8	1.456 (4)	C11—Cl4	1.751 (3)
N9—C18	1.341 (4)	C13—H13A	0.9600
N9—C15	1.350 (4)	C13—H13B	0.9600
N10—C17	1.330 (4)	C13—H13C	0.9600
N10—C18	1.346 (4)	C14—H14A	0.9600
N11—C18	1.348 (4)	C14—H14B	0.9600
N11—H11B	0.8716	C14—H14C	0.9600
N11—H11A	0.8741	C15—C16	1.399 (4)
N12—C15	1.349 (4)	C16—C17	1.352 (4)
N12—C14	1.444 (4)	C16—H16	0.9300
N12—C13	1.458 (4)	C17—Cl3	1.742 (3)
N13—C21	1.353 (4)	C19—H19A	0.9600
N13—C20	1.450 (4)	C19—H19B	0.9600
N13—C19	1.452 (5)	C19—H19C	0.9600
N14—C24	1.337 (4)	C20—H20A	0.9600
N14—C21	1.338 (4)	C20—H20B	0.9600
N15—C23	1.325 (4)	C20—H20C	0.9600
N15—C24	1.353 (4)	C21—C22	1.409 (4)
N16—C24	1.348 (4)	C22—C23	1.356 (4)
N16—H16A	0.8773	C22—H22	0.9300
N16—H16B	0.8682	C23—Cl2	1.747 (3)
C4—N1—C1	116.3 (3)	H8B—C8—H8C	109.5
C3—N2—C4	113.1 (3)	N8—C9—H9A	109.5
C4—N3—H3A	122.0	N8—C9—H9B	109.5
C4—N3—H3B	118.9	H9A—C9—H9B	109.5
H3A—N3—H3B	119.1	N8—C9—H9C	109.5
C1—N4—C5	121.6 (3)	H9A—C9—H9C	109.5
C1—N4—C6	121.2 (3)	H9B—C9—H9C	109.5
C5—N4—C6	116.9 (3)	C11—C10—C7	115.4 (3)
C11—N5—C12	113.1 (3)	C11—C10—H10	122.3
C12—N6—C7	117.2 (2)	C7—C10—H10	122.3
C12—N7—H7A	118.4	N5—C11—C10	127.1 (3)
C12—N7—H7B	116.9	N5—C11—Cl4	114.1 (2)
H7A—N7—H7B	124.6	C10—C11—Cl4	118.8 (2)
C7—N8—C9	121.4 (3)	N6—C12—N7	117.7 (3)
C7—N8—C8	121.0 (3)	N6—C12—N5	126.5 (3)
C9—N8—C8	117.3 (3)	N7—C12—N5	115.8 (3)
C18—N9—C15	116.7 (3)	N12—C13—H13A	109.5
C17—N10—C18	113.7 (3)	N12—C13—H13B	109.5
C18—N11—H11B	119.1	H13A—C13—H13B	109.5
C18—N11—H11A	120.3	N12—C13—H13C	109.5
H11B—N11—H11A	117.1	H13A—C13—H13C	109.5
C15—N12—C14	122.1 (3)	H13B—C13—H13C	109.5
C15—N12—C13	121.0 (3)	N12—C14—H14A	109.5
C14—N12—C13	116.9 (3)	N12—C14—H14B	109.5
C21—N13—C20	121.8 (3)	H14A—C14—H14B	109.5
C21—N13—C19	121.7 (3)	N12—C14—H14C	109.5
C20—N13—C19	116.5 (3)	H14A—C14—H14C	109.5
C24—N14—C21	116.9 (3)	H14B—C14—H14C	109.5
C23—N15—C24	112.7 (3)	N12—C15—N9	117.0 (3)
C24—N16—H16A	120.6	N12—C15—C16	122.0 (3)
C24—N16—H16B	116.8	N9—C15—C16	120.9 (3)
H16A—N16—H16B	117.8	C17—C16—C15	115.9 (3)
N4—C1—N1	116.8 (3)	C17—C16—H16	122.1
N4—C1—C2	122.5 (3)	C15—C16—H16	122.1
N1—C1—C2	120.7 (3)	N10—C17—C16	126.1 (3)
C3—C2—C1	115.4 (3)	N10—C17—Cl3	114.6 (2)
C3—C2—H2	122.3	C16—C17—Cl3	119.3 (2)
C1—C2—H2	122.3	N9—C18—N10	126.6 (3)
N2—C3—C2	126.7 (3)	N9—C18—N11	117.6 (3)
N2—C3—Cl1	114.8 (2)	N10—C18—N11	115.8 (3)
C2—C3—Cl1	118.5 (2)	N13—C19—H19A	109.5
N1—C4—N2	127.6 (3)	N13—C19—H19B	109.5
N1—C4—N3	116.7 (3)	H19A—C19—H19B	109.5
N2—C4—N3	115.7 (3)	N13—C19—H19C	109.5
N4—C5—H5A	109.5	H19A—C19—H19C	109.5
N4—C5—H5B	109.5	H19B—C19—H19C	109.5
H5A—C5—H5B	109.5	N13—C20—H20A	109.5
N4—C5—H5C	109.5	N13—C20—H20B	109.5
H5A—C5—H5C	109.5	H20A—C20—H20B	109.5
H5B—C5—H5C	109.5	N13—C20—H20C	109.5
N4—C6—H6A	109.5	H20A—C20—H20C	109.5
N4—C6—H6B	109.5	H20B—C20—H20C	109.5
H6A—C6—H6B	109.5	N14—C21—N13	116.9 (3)
N4—C6—H6C	109.5	N14—C21—C22	121.0 (3)
H6A—C6—H6C	109.5	N13—C21—C22	122.1 (3)
H6B—C6—H6C	109.5	C23—C22—C21	115.3 (3)
N8—C7—N6	117.9 (3)	C23—C22—H22	122.4
N8—C7—C10	121.8 (3)	C21—C22—H22	122.4
N6—C7—C10	120.4 (3)	N15—C23—C22	126.9 (3)
N8—C8—H8A	109.5	N15—C23—Cl2	114.3 (2)
N8—C8—H8B	109.5	C22—C23—Cl2	118.8 (3)
H8A—C8—H8B	109.5	N14—C24—N16	117.3 (3)
N8—C8—H8C	109.5	N14—C24—N15	127.2 (3)
H8A—C8—H8C	109.5	N16—C24—N15	115.5 (3)
C5—N4—C1—N1	−3.6 (5)	C14—N12—C15—N9	5.5 (5)
C6—N4—C1—N1	−177.5 (3)	C13—N12—C15—N9	−174.5 (3)
C5—N4—C1—C2	176.3 (3)	C14—N12—C15—C16	−174.8 (3)
C6—N4—C1—C2	2.4 (5)	C13—N12—C15—C16	5.3 (5)
C4—N1—C1—N4	175.7 (3)	C18—N9—C15—N12	−177.3 (3)
C4—N1—C1—C2	−4.2 (4)	C18—N9—C15—C16	2.9 (4)
N4—C1—C2—C3	−178.4 (3)	N12—C15—C16—C17	177.1 (3)
N1—C1—C2—C3	1.4 (5)	N9—C15—C16—C17	−3.2 (5)
C4—N2—C3—C2	−1.8 (5)	C18—N10—C17—C16	1.8 (5)
C4—N2—C3—Cl1	178.1 (2)	C18—N10—C17—Cl3	−178.0 (2)
C1—C2—C3—N2	1.8 (5)	C15—C16—C17—N10	0.8 (5)
C1—C2—C3—Cl1	−178.2 (2)	C15—C16—C17—Cl3	−179.5 (2)
C1—N1—C4—N2	4.4 (5)	C15—N9—C18—N10	−0.2 (5)
C1—N1—C4—N3	−177.7 (3)	C15—N9—C18—N11	179.0 (3)
C3—N2—C4—N1	−1.5 (5)	C17—N10—C18—N9	−2.1 (5)
C3—N2—C4—N3	−179.4 (3)	C17—N10—C18—N11	178.7 (3)
C9—N8—C7—N6	−5.8 (5)	C24—N14—C21—N13	−180.0 (3)
C8—N8—C7—N6	−179.5 (3)	C24—N14—C21—C22	0.4 (4)
C9—N8—C7—C10	175.3 (3)	C20—N13—C21—N14	−1.5 (5)
C8—N8—C7—C10	1.6 (5)	C19—N13—C21—N14	176.5 (3)
C12—N6—C7—N8	176.8 (3)	C20—N13—C21—C22	178.1 (3)
C12—N6—C7—C10	−4.3 (4)	C19—N13—C21—C22	−3.9 (5)
N8—C7—C10—C11	−179.9 (3)	N14—C21—C22—C23	−0.3 (4)
N6—C7—C10—C11	1.2 (4)	N13—C21—C22—C23	−179.9 (3)
C12—N5—C11—C10	−0.3 (5)	C24—N15—C23—C22	1.0 (5)
C12—N5—C11—Cl4	179.4 (2)	C24—N15—C23—Cl2	−178.6 (2)
C7—C10—C11—N5	1.2 (5)	C21—C22—C23—N15	−0.4 (5)
C7—C10—C11—Cl4	−178.6 (2)	C21—C22—C23—Cl2	179.2 (2)
C7—N6—C12—N7	−175.9 (3)	C21—N14—C24—N16	178.2 (3)
C7—N6—C12—N5	5.5 (5)	C21—N14—C24—N15	0.3 (5)
C11—N5—C12—N6	−3.2 (5)	C23—N15—C24—N14	−1.0 (5)
C11—N5—C12—N7	178.2 (3)	C23—N15—C24—N16	−178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11B···N1	0.87	2.48	3.310 (4)	161
N3—H3A···N9	0.86	2.41	3.264 (4)	168
N16—H16B···N15i	0.87	2.17	3.038 (4)	174
N11—H11A···N10ii	0.87	2.21	3.086 (4)	174
N7—H7B···N5iii	0.88	2.19	3.064 (3)	178
N3—H3B···N6iv	0.89	2.35	3.230 (4)	169
N7—H7A···N2iv	0.87	2.33	3.136 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11B⋯N1	0.87	2.48	3.310 (4)	161
N3—H3A⋯N9	0.86	2.41	3.264 (4)	168
N16—H16B⋯N15i	0.87	2.17	3.038 (4)	174
N11—H11A⋯N10ii	0.87	2.21	3.086 (4)	174
N7—H7B⋯N5iii	0.88	2.19	3.064 (3)	178
N3—H3B⋯N6iv	0.89	2.35	3.230 (4)	169
N7—H7A⋯N2iv	0.87	2.33	3.136 (3)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .