6-Chloro-2-methyl­thio-4-[(2-phenyl­ethyl)­amino]­pyrimidine

The structure of the title compound, C₂₆H₂₈Cl₂N₆S₂, comprises two independent mol­ecules that separately associate via N—H...N hydrogen-bonding interactions to like mol­ecules. The dihedral angles between the two rings in each case are 25.79 (12) and 10.72 (12)°.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.123
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

NO COMMENT

S2. Experimental

Crystals obtained from Spa Contract Synthesis.

S3. Refinement

All H atoms were included in the refinement at calculated positions as riding models, with C—H set to 0.95 (Ar—H), 0.98 (CH₃) and 0.99 Å (CH₂), except for the amine H atoms which were located on difference syntheses and for which both positional and displacement parameters were refined.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for molecule A, showing 30% probability ellipsoids.
	Fig. 2. The molecular configuration and atom-numbering scheme for molecule B, showing 30% probability ellipsoids.

6-Chloro-2-methylthio-4-[(2-phenylethyl)amino]pyrimidine

Crystal data

C26H28Cl2N6S2	Dx = 1.357 Mg m^−3
Mr = 559.56	Melting point: 360 - 362 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.038 (4) Å	Cell parameters from 11927 reflections
b = 11.358 (2) Å	θ = 2.9–27.5°
c = 12.043 (2) Å	µ = 0.42 mm^−1
β = 92.03 (3)°	T = 150 K
V = 2739.3 (10) Å^3	Block, colourless
Z = 4	0.20 × 0.18 × 0.10 mm
F(000) = 1168

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	6216 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	4274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −25→26
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→14
Tmin = 0.921, Tmax = 0.960	l = −15→15
23836 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.5559P] where P = (Fo^2 + 2Fc^2)/3
6216 reflections	(Δ/σ)max < 0.001
335 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

16.4013 (0.0129) x - 6.5194 (0.0085) y - 0.6463 (0.0102) z = 2.1680 (0.0037)

* -0.0039 (0.0014) N1A * 0.0042 (0.0014) C2A * -0.0003 (0.0013) N3A * -0.0034 (0.0014) C4A * 0.0033 (0.0015) C5A * 0.0002 (0.0015) C6A

Rms deviation of fitted atoms = 0.0030

- 12.5759 (0.0193) x + 7.4466 (0.0103) y + 5.3213 (0.0132) z = 0.8325 (0.0067)

Angle to previous plane (with approximate e.s.d.) = 25.79 (0.12)

* 0.0057 (0.0018) C44A * -0.0061 (0.0019) C45A * 0.0012 (0.0019) C46A * 0.0041 (0.0020) C47A * -0.0045 (0.0020) C48A * -0.0004 (0.0020) C49A

Rms deviation of fitted atoms = 0.0043

14.8169 (0.0135) x - 6.9115 (0.0079) y - 3.7824 (0.0096) z = 2.1931 (0.0109)

Angle to previous plane (with approximate e.s.d.) = 10.28 (0.15)

* 0.0011 (0.0013) N1B * 0.0004 (0.0014) C2B * -0.0030 (0.0013) N3B * 0.0041 (0.0013) C4B * -0.0025 (0.0014) C5B * 0.0000 (0.0014) C6B

Rms deviation of fitted atoms = 0.0023

16.9296 (0.0134) x - 5.7518 (0.0096) y - 2.4373 (0.0118) z = 5.8046 (0.0182)

Angle to previous plane (with approximate e.s.d.) = 10.72 (0.12)

* -0.0007 (0.0015) C44B * 0.0008 (0.0018) C45B * -0.0003 (0.0018) C46B * -0.0004 (0.0017) C47B * 0.0005 (0.0016) C48B * 0.0000 (0.0016) C49B

Rms deviation of fitted atoms = 0.0005

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.21983 (9)	0.22821 (17)	−0.07175 (13)	0.0299 (4)
C2A	0.18349 (10)	0.13330 (19)	−0.04914 (17)	0.0261 (5)
S21A	0.15169 (3)	0.06327 (6)	−0.16984 (4)	0.03741 (17)
C22A	0.10681 (14)	−0.0583 (2)	−0.1144 (2)	0.0475 (7)
H21A	0.1371	−0.1060	−0.0672	0.059*
H22A	0.0885	−0.1068	−0.1755	0.059*
H23A	0.0702	−0.0288	−0.0702	0.059*
N3A	0.16950 (8)	0.08903 (15)	0.04949 (13)	0.0259 (4)
C4A	0.19588 (10)	0.14708 (19)	0.13799 (16)	0.0256 (5)
N41A	0.18329 (10)	0.10783 (18)	0.23989 (15)	0.0348 (5)
H4A	0.1987 (12)	0.154 (2)	0.293 (2)	0.045 (8)*
C42A	0.14349 (14)	0.0053 (2)	0.26622 (19)	0.0431 (6)
H41A	0.1733	−0.0595	0.2917	0.054*
H42A	0.1183	−0.0214	0.1987	0.054*
C43A	0.09690 (18)	0.0336 (3)	0.3530 (3)	0.0742 (10)
H43A	0.0632	0.0896	0.3222	0.093*
H44A	0.1218	0.0741	0.4143	0.093*
C44A	0.06088 (12)	−0.0709 (2)	0.4006 (2)	0.0434 (6)
C45A	0.00747 (13)	−0.1226 (3)	0.3445 (2)	0.0477 (7)
H45A	−0.0055	−0.0949	0.2725	0.060*
C46A	−0.02761 (13)	−0.2137 (3)	0.3905 (2)	0.0501 (7)
H46A	−0.0647	−0.2475	0.3507	0.063*
C47A	−0.00903 (14)	−0.2555 (3)	0.4935 (3)	0.0528 (7)
H47A	−0.0331	−0.3182	0.5257	0.066*
C48A	0.04458 (16)	−0.2063 (3)	0.5497 (2)	0.0593 (8)
H48A	0.0580	−0.2356	0.6208	0.074*
C49A	0.07907 (13)	−0.1149 (3)	0.5040 (2)	0.0531 (7)
H49A	0.1160	−0.0814	0.5443	0.066*
C5A	0.23579 (10)	0.2477 (2)	0.12570 (16)	0.0281 (5)
H5A	0.2549	0.2888	0.1877	0.035*
C6A	0.24516 (10)	0.2822 (2)	0.01983 (17)	0.0289 (5)
Cl6A	0.29257 (4)	0.40626 (6)	−0.00536 (5)	0.0552 (2)
N1B	0.51355 (8)	0.71905 (16)	0.11772 (13)	0.0263 (4)
C2B	0.55408 (9)	0.81211 (18)	0.10665 (15)	0.0222 (4)
S21B	0.59942 (3)	0.84610 (5)	0.22985 (4)	0.03081 (16)
C22B	0.64533 (11)	0.9736 (2)	0.18981 (17)	0.0332 (5)
H21B	0.6769	0.9517	0.1330	0.042*
H22B	0.6699	1.0056	0.2548	0.042*
H23B	0.6143	1.0332	0.1598	0.042*
N3B	0.56205 (8)	0.87841 (15)	0.01758 (12)	0.0218 (4)
C4B	0.52500 (9)	0.84814 (18)	−0.07409 (15)	0.0225 (4)
N41B	0.53134 (9)	0.91376 (16)	−0.16581 (14)	0.0246 (4)
H4B	0.5172 (11)	0.884 (2)	−0.224 (2)	0.035 (7)*
C42B	0.57422 (10)	1.01590 (18)	−0.17058 (16)	0.0255 (5)
H41B	0.5718	1.0597	−0.0997	0.032*
H42B	0.5571	1.0683	−0.2308	0.032*
C43B	0.64724 (11)	0.9870 (2)	−0.19073 (18)	0.0316 (5)
H43B	0.6644	0.9317	−0.1329	0.040*
H44B	0.6507	0.9482	−0.2639	0.040*
C44B	0.68860 (10)	1.09734 (19)	−0.18786 (17)	0.0283 (5)
C45B	0.71708 (12)	1.1389 (2)	−0.08867 (18)	0.0375 (6)
H45B	0.7118	1.0949	−0.0225	0.047*
C46B	0.75285 (13)	1.2424 (2)	−0.08407 (19)	0.0418 (6)
H46B	0.7717	1.2689	−0.0150	0.052*
C47B	0.76148 (12)	1.3080 (2)	−0.17899 (18)	0.0366 (5)
H47B	0.7861	1.3795	−0.1759	0.046*
C48B	0.73374 (11)	1.2681 (2)	−0.27793 (17)	0.0346 (5)
H48B	0.7394	1.3125	−0.3438	0.043*
C49B	0.69775 (11)	1.1644 (2)	−0.28296 (17)	0.0319 (5)
H49B	0.6790	1.1385	−0.3523	0.040*
C5B	0.48059 (10)	0.75290 (19)	−0.07229 (16)	0.0261 (5)
H5B	0.4539	0.7314	−0.1359	0.033*
C6B	0.47762 (10)	0.69297 (19)	0.02493 (16)	0.0253 (4)
Cl6B	0.42403 (3)	0.57459 (5)	0.03666 (5)	0.04045 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0328 (10)	0.0318 (11)	0.0250 (9)	−0.0062 (8)	−0.0011 (7)	0.0006 (8)
C2A	0.0225 (11)	0.0268 (12)	0.0290 (11)	0.0003 (9)	0.0016 (8)	−0.0032 (9)
S21A	0.0460 (4)	0.0389 (4)	0.0272 (3)	−0.0109 (3)	0.0001 (2)	−0.0076 (2)
C22A	0.0563 (17)	0.0384 (16)	0.0477 (15)	−0.0184 (13)	0.0023 (12)	−0.0100 (12)
N3A	0.0278 (9)	0.0243 (10)	0.0258 (9)	0.0001 (8)	0.0029 (7)	−0.0007 (7)
C4A	0.0252 (11)	0.0252 (12)	0.0264 (11)	0.0026 (9)	0.0031 (8)	0.0023 (8)
N41A	0.0484 (12)	0.0318 (12)	0.0247 (10)	−0.0078 (9)	0.0062 (8)	−0.0004 (8)
C42A	0.0627 (17)	0.0316 (14)	0.0359 (12)	−0.0082 (12)	0.0166 (11)	0.0024 (10)
C43A	0.075 (2)	0.051 (2)	0.101 (3)	−0.0199 (17)	0.0514 (19)	−0.0166 (18)
C44A	0.0384 (14)	0.0403 (16)	0.0530 (15)	−0.0068 (11)	0.0198 (12)	−0.0084 (12)
C45A	0.0490 (16)	0.0533 (18)	0.0410 (14)	−0.0028 (13)	0.0044 (11)	0.0019 (12)
C46A	0.0365 (15)	0.0479 (18)	0.0662 (18)	−0.0072 (13)	0.0041 (12)	−0.0122 (14)
C47A	0.0532 (17)	0.0352 (16)	0.0720 (19)	−0.0007 (13)	0.0295 (14)	0.0049 (14)
C48A	0.065 (2)	0.067 (2)	0.0470 (16)	0.0172 (17)	0.0070 (14)	0.0080 (15)
C49A	0.0342 (15)	0.065 (2)	0.0606 (18)	0.0013 (13)	0.0011 (12)	−0.0179 (15)
C5A	0.0275 (11)	0.0319 (13)	0.0247 (10)	−0.0021 (9)	−0.0022 (8)	−0.0020 (9)
C6A	0.0275 (11)	0.0288 (13)	0.0301 (11)	−0.0052 (9)	−0.0009 (8)	0.0036 (9)
Cl6A	0.0730 (5)	0.0579 (5)	0.0343 (3)	−0.0420 (4)	−0.0042 (3)	0.0065 (3)
N1B	0.0293 (10)	0.0245 (10)	0.0248 (9)	−0.0022 (8)	−0.0030 (7)	0.0024 (7)
C2B	0.0234 (10)	0.0226 (11)	0.0205 (9)	0.0007 (8)	−0.0008 (7)	0.0006 (8)
S21B	0.0357 (3)	0.0351 (3)	0.0211 (3)	−0.0090 (2)	−0.0072 (2)	0.0040 (2)
C22B	0.0374 (13)	0.0338 (14)	0.0280 (11)	−0.0099 (10)	−0.0063 (9)	0.0010 (9)
N3B	0.0244 (9)	0.0224 (9)	0.0185 (8)	0.0004 (7)	−0.0002 (6)	−0.0014 (7)
C4B	0.0228 (10)	0.0241 (12)	0.0203 (9)	0.0026 (8)	−0.0006 (7)	−0.0031 (8)
N41B	0.0289 (10)	0.0273 (11)	0.0172 (9)	−0.0027 (8)	−0.0022 (7)	0.0005 (7)
C42B	0.0315 (12)	0.0211 (12)	0.0237 (10)	−0.0004 (9)	−0.0002 (8)	0.0033 (8)
C43B	0.0313 (12)	0.0269 (13)	0.0370 (12)	−0.0002 (10)	0.0069 (9)	−0.0032 (9)
C44B	0.0260 (11)	0.0273 (13)	0.0317 (11)	0.0044 (9)	0.0046 (8)	−0.0002 (9)
C45B	0.0475 (15)	0.0383 (15)	0.0266 (12)	−0.0071 (11)	0.0009 (10)	0.0070 (10)
C46B	0.0532 (16)	0.0440 (16)	0.0275 (12)	−0.0163 (12)	−0.0072 (10)	0.0030 (10)
C47B	0.0400 (13)	0.0308 (14)	0.0388 (13)	−0.0078 (11)	0.0011 (10)	0.0012 (10)
C48B	0.0436 (14)	0.0323 (14)	0.0281 (11)	0.0013 (11)	0.0054 (9)	0.0084 (9)
C49B	0.0360 (13)	0.0345 (14)	0.0251 (11)	0.0019 (10)	0.0020 (9)	−0.0004 (9)
C5B	0.0302 (11)	0.0262 (12)	0.0215 (10)	−0.0019 (9)	−0.0035 (8)	−0.0037 (8)
C6B	0.0256 (11)	0.0223 (12)	0.0278 (11)	−0.0030 (9)	−0.0019 (8)	0.0007 (8)
Cl6B	0.0442 (4)	0.0359 (4)	0.0406 (3)	−0.0188 (3)	−0.0075 (2)	0.0082 (2)

Geometric parameters (Å, º)

N1A—C2A	1.334 (3)	N1B—C6B	1.341 (2)
N1A—C6A	1.346 (3)	N1B—C2B	1.343 (3)
C2A—N3A	1.329 (3)	C2B—N3B	1.325 (2)
C2A—S21A	1.757 (2)	C2B—S21B	1.7551 (19)
S21A—C22A	1.790 (3)	S21B—C22B	1.791 (2)
C22A—H21A	0.9800	C22B—H21B	0.9800
C22A—H22A	0.9800	C22B—H22B	0.9800
C22A—H23A	0.9800	C22B—H23B	0.9800
N3A—C4A	1.345 (3)	N3B—C4B	1.353 (2)
C4A—N41A	1.338 (3)	C4B—N41B	1.342 (3)
C4A—C5A	1.406 (3)	C4B—C5B	1.401 (3)
N41A—C42A	1.453 (3)	N41B—C42B	1.446 (3)
N41A—H4A	0.87 (3)	N41B—H4B	0.82 (2)
C42A—C43A	1.462 (4)	C42B—C43B	1.527 (3)
C42A—H41A	0.9900	C42B—H41B	0.9900
C42A—H42A	0.9900	C42B—H42B	0.9900
C43A—C44A	1.512 (4)	C43B—C44B	1.503 (3)
C43A—H43A	0.9900	C43B—H43B	0.9900
C43A—H44A	0.9900	C43B—H44B	0.9900
C44A—C49A	1.379 (4)	C44B—C45B	1.388 (3)
C44A—C45A	1.377 (4)	C44B—C49B	1.393 (3)
C45A—C46A	1.378 (4)	C45B—C46B	1.377 (3)
C45A—H45A	0.9500	C45B—H45B	0.9500
C46A—C47A	1.367 (4)	C46B—C47B	1.381 (3)
C46A—H46A	0.9500	C46B—H46B	0.9500
C47A—C48A	1.369 (4)	C47B—C48B	1.374 (3)
C47A—H47A	0.9500	C47B—H47B	0.9500
C48A—C49A	1.373 (4)	C48B—C49B	1.381 (3)
C48A—H48A	0.9500	C48B—H48B	0.9500
C49A—H49A	0.9500	C49B—H49B	0.9500
C5A—C6A	1.353 (3)	C5B—C6B	1.357 (3)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—Cl6A	1.732 (2)	C6B—Cl6B	1.730 (2)
C2A—N1A—C6A	113.19 (17)	C6B—N1B—C2B	113.57 (16)
N3A—C2A—N1A	128.47 (18)	N3B—C2B—N1B	128.21 (17)
N3A—C2A—S21A	119.11 (16)	N3B—C2B—S21B	119.07 (15)
N1A—C2A—S21A	112.42 (15)	N1B—C2B—S21B	112.71 (14)
C2A—S21A—C22A	102.31 (11)	C2B—S21B—C22B	101.87 (10)
S21A—C22A—H21A	109.5	S21B—C22B—H21B	109.5
S21A—C22A—H22A	109.5	S21B—C22B—H22B	109.5
H21A—C22A—H22A	109.5	H21B—C22B—H22B	109.5
S21A—C22A—H23A	109.5	S21B—C22B—H23B	109.5
H21A—C22A—H23A	109.5	H21B—C22B—H23B	109.5
H22A—C22A—H23A	109.5	H22B—C22B—H23B	109.5
C2A—N3A—C4A	115.68 (17)	C2B—N3B—C4B	115.97 (17)
N41A—C4A—N3A	118.81 (19)	N41B—C4B—N3B	117.73 (18)
N41A—C4A—C5A	119.59 (19)	N41B—C4B—C5B	121.33 (17)
N3A—C4A—C5A	121.60 (17)	N3B—C4B—C5B	120.93 (17)
C4A—N41A—C42A	126.2 (2)	C4B—N41B—C42B	123.49 (17)
C4A—N41A—H4A	113.8 (17)	C4B—N41B—H4B	116.0 (18)
C42A—N41A—H4A	119.9 (17)	C42B—N41B—H4B	118.8 (17)
N41A—C42A—C43A	110.5 (2)	N41B—C42B—C43B	114.05 (18)
N41A—C42A—H41A	109.6	N41B—C42B—H41B	108.7
C43A—C42A—H41A	109.6	C43B—C42B—H41B	108.7
N41A—C42A—H42A	109.6	N41B—C42B—H42B	108.7
C43A—C42A—H42A	109.6	C43B—C42B—H42B	108.7
H41A—C42A—H42A	108.1	H41B—C42B—H42B	107.6
C42A—C43A—C44A	115.1 (3)	C44B—C43B—C42B	110.34 (18)
C42A—C43A—H43A	108.5	C44B—C43B—H43B	109.6
C44A—C43A—H43A	108.5	C42B—C43B—H43B	109.6
C42A—C43A—H44A	108.5	C44B—C43B—H44B	109.6
C44A—C43A—H44A	108.5	C42B—C43B—H44B	109.6
H43A—C43A—H44A	107.5	H43B—C43B—H44B	108.1
C49A—C44A—C45A	117.7 (3)	C45B—C44B—C49B	117.4 (2)
C49A—C44A—C43A	120.8 (3)	C45B—C44B—C43B	120.86 (19)
C45A—C44A—C43A	121.5 (3)	C49B—C44B—C43B	121.74 (19)
C46A—C45A—C44A	121.4 (3)	C46B—C45B—C44B	121.5 (2)
C46A—C45A—H45A	119.3	C46B—C45B—H45B	119.3
C44A—C45A—H45A	119.3	C44B—C45B—H45B	119.3
C47A—C46A—C45A	120.0 (3)	C47B—C46B—C45B	120.5 (2)
C47A—C46A—H46A	120.0	C47B—C46B—H46B	119.7
C45A—C46A—H46A	120.0	C45B—C46B—H46B	119.7
C48A—C47A—C46A	119.3 (3)	C48B—C47B—C46B	118.8 (2)
C48A—C47A—H47A	120.3	C48B—C47B—H47B	120.6
C46A—C47A—H47A	120.3	C46B—C47B—H47B	120.6
C47A—C48A—C49A	120.6 (3)	C47B—C48B—C49B	120.9 (2)
C47A—C48A—H48A	119.7	C47B—C48B—H48B	119.5
C49A—C48A—H48A	119.7	C49B—C48B—H48B	119.5
C44A—C49A—C48A	121.0 (3)	C48B—C49B—C44B	120.9 (2)
C44A—C49A—H49A	119.5	C48B—C49B—H49B	119.5
C48A—C49A—H49A	119.5	C44B—C49B—H49B	119.5
C6A—C5A—C4A	115.68 (19)	C6B—C5B—C4B	116.59 (17)
C6A—C5A—H5A	122.2	C6B—C5B—H5B	121.7
C4A—C5A—H5A	122.2	C4B—C5B—H5B	121.7
N1A—C6A—C5A	125.4 (2)	N1B—C6B—C5B	124.72 (19)
N1A—C6A—Cl6A	114.87 (15)	N1B—C6B—Cl6B	114.84 (15)
C5A—C6A—Cl6A	119.75 (16)	C5B—C6B—Cl6B	120.43 (15)
C6A—N1A—C2A—N3A	0.9 (3)	C6B—N1B—C2B—N3B	0.1 (3)
C6A—N1A—C2A—S21A	−179.34 (15)	C6B—N1B—C2B—S21B	178.91 (15)
N3A—C2A—S21A—C22A	−0.6 (2)	N3B—C2B—S21B—C22B	0.72 (19)
N1A—C2A—S21A—C22A	179.61 (17)	N1B—C2B—S21B—C22B	−178.21 (16)
N1A—C2A—N3A—C4A	−0.5 (3)	N1B—C2B—N3B—C4B	−0.5 (3)
S21A—C2A—N3A—C4A	179.67 (15)	S21B—C2B—N3B—C4B	−179.23 (14)
C2A—N3A—C4A—N41A	179.43 (19)	C2B—N3B—C4B—N41B	179.54 (18)
C2A—N3A—C4A—C5A	−0.2 (3)	C2B—N3B—C4B—C5B	0.8 (3)
N3A—C4A—N41A—C42A	0.7 (3)	N3B—C4B—N41B—C42B	−1.5 (3)
C5A—C4A—N41A—C42A	−179.6 (2)	C5B—C4B—N41B—C42B	177.22 (19)
C4A—N41A—C42A—C43A	−133.7 (3)	C4B—N41B—C42B—C43B	82.9 (2)
N41A—C42A—C43A—C44A	−170.4 (3)	N41B—C42B—C43B—C44B	−176.75 (16)
C42A—C43A—C44A—C49A	104.5 (3)	C42B—C43B—C44B—C45B	88.5 (2)
C42A—C43A—C44A—C45A	−78.0 (4)	C42B—C43B—C44B—C49B	−88.9 (2)
C49A—C44A—C45A—C46A	1.2 (4)	C49B—C44B—C45B—C46B	0.2 (4)
C43A—C44A—C45A—C46A	−176.4 (3)	C43B—C44B—C45B—C46B	−177.4 (2)
C44A—C45A—C46A—C47A	−0.8 (4)	C44B—C45B—C46B—C47B	−0.1 (4)
C45A—C46A—C47A—C48A	−0.2 (4)	C45B—C46B—C47B—C48B	0.0 (4)
C46A—C47A—C48A—C49A	0.7 (4)	C46B—C47B—C48B—C49B	0.1 (4)
C45A—C44A—C49A—C48A	−0.6 (4)	C47B—C48B—C49B—C44B	0.0 (3)
C43A—C44A—C49A—C48A	177.0 (3)	C45B—C44B—C49B—C48B	−0.1 (3)
C47A—C48A—C49A—C44A	−0.3 (4)	C43B—C44B—C49B—C48B	177.4 (2)
N41A—C4A—C5A—C6A	−179.1 (2)	N41B—C4B—C5B—C6B	−179.46 (19)
N3A—C4A—C5A—C6A	0.6 (3)	N3B—C4B—C5B—C6B	−0.8 (3)
C2A—N1A—C6A—C5A	−0.4 (3)	C2B—N1B—C6B—C5B	0.0 (3)
C2A—N1A—C6A—Cl6A	−179.84 (16)	C2B—N1B—C6B—Cl6B	−179.23 (15)
C4A—C5A—C6A—N1A	−0.2 (3)	C4B—C5B—C6B—N1B	0.4 (3)
C4A—C5A—C6A—Cl6A	179.15 (16)	C4B—C5B—C6B—Cl6B	179.51 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N41A—H4A···N1A^i	0.87 (3)	2.14 (3)	3.005 (3)	171 (2)
N41B—H4B···N1B^ii	0.82 (2)	2.24 (3)	3.022 (2)	161 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2.