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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)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001945/cf6020sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001945/cf6020Isup2.hkl
Contains datablock I

CCDC reference: 159839

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




Comment top

NO COMMENT

Experimental top

Crystals obtained from Spa Contract Synthesis.

Refinement top

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 top

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 top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for molecule A, showing 30% probability ellipsoids.
[Figure 2] 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 top
Crystal data top
C26H28Cl2N6S2Dx = 1.357 Mg m3
Mr = 559.56Melting point: 360 - 362 K K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.038 (4) ÅCell parameters from 11927 reflections
b = 11.358 (2) Åθ = 2.9–27.5°
c = 12.043 (2) ŵ = 0.42 mm1
β = 92.03 (3)°T = 150 K
V = 2739.3 (10) Å3Block, colourless
Z = 40.20 × 0.18 × 0.10 mm
F(000) = 1168
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
6216 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode4274 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = 2526
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1414
Tmin = 0.921, Tmax = 0.960l = 1515
23836 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.5559P]
where P = (Fo2 + 2Fc2)/3
6216 reflections(Δ/σ)max < 0.001
335 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C26H28Cl2N6S2V = 2739.3 (10) Å3
Mr = 559.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.038 (4) ŵ = 0.42 mm1
b = 11.358 (2) ÅT = 150 K
c = 12.043 (2) Å0.20 × 0.18 × 0.10 mm
β = 92.03 (3)°
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
6216 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
4274 reflections with I > 2σ(I)
Tmin = 0.921, Tmax = 0.960Rint = 0.083
23836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.44 e Å3
6216 reflectionsΔρmin = 0.52 e Å3
335 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N1A0.21983 (9)0.22821 (17)0.07175 (13)0.0299 (4)
C2A0.18349 (10)0.13330 (19)0.04914 (17)0.0261 (5)
S21A0.15169 (3)0.06327 (6)0.16984 (4)0.03741 (17)
C22A0.10681 (14)0.0583 (2)0.1144 (2)0.0475 (7)
H21A0.13710.10600.06720.059*
H22A0.08850.10680.17550.059*
H23A0.07020.02880.07020.059*
N3A0.16950 (8)0.08903 (15)0.04949 (13)0.0259 (4)
C4A0.19588 (10)0.14708 (19)0.13799 (16)0.0256 (5)
N41A0.18329 (10)0.10783 (18)0.23989 (15)0.0348 (5)
H4A0.1987 (12)0.154 (2)0.293 (2)0.045 (8)*
C42A0.14349 (14)0.0053 (2)0.26622 (19)0.0431 (6)
H41A0.17330.05950.29170.054*
H42A0.11830.02140.19870.054*
C43A0.09690 (18)0.0336 (3)0.3530 (3)0.0742 (10)
H43A0.06320.08960.32220.093*
H44A0.12180.07410.41430.093*
C44A0.06088 (12)0.0709 (2)0.4006 (2)0.0434 (6)
C45A0.00747 (13)0.1226 (3)0.3445 (2)0.0477 (7)
H45A0.00550.09490.27250.060*
C46A0.02761 (13)0.2137 (3)0.3905 (2)0.0501 (7)
H46A0.06470.24750.35070.063*
C47A0.00903 (14)0.2555 (3)0.4935 (3)0.0528 (7)
H47A0.03310.31820.52570.066*
C48A0.04458 (16)0.2063 (3)0.5497 (2)0.0593 (8)
H48A0.05800.23560.62080.074*
C49A0.07907 (13)0.1149 (3)0.5040 (2)0.0531 (7)
H49A0.11600.08140.54430.066*
C5A0.23579 (10)0.2477 (2)0.12570 (16)0.0281 (5)
H5A0.25490.28880.18770.035*
C6A0.24516 (10)0.2822 (2)0.01983 (17)0.0289 (5)
Cl6A0.29257 (4)0.40626 (6)0.00536 (5)0.0552 (2)
N1B0.51355 (8)0.71905 (16)0.11772 (13)0.0263 (4)
C2B0.55408 (9)0.81211 (18)0.10665 (15)0.0222 (4)
S21B0.59942 (3)0.84610 (5)0.22985 (4)0.03081 (16)
C22B0.64533 (11)0.9736 (2)0.18981 (17)0.0332 (5)
H21B0.67690.95170.13300.042*
H22B0.66991.00560.25480.042*
H23B0.61431.03320.15980.042*
N3B0.56205 (8)0.87841 (15)0.01758 (12)0.0218 (4)
C4B0.52500 (9)0.84814 (18)0.07409 (15)0.0225 (4)
N41B0.53134 (9)0.91376 (16)0.16581 (14)0.0246 (4)
H4B0.5172 (11)0.884 (2)0.224 (2)0.035 (7)*
C42B0.57422 (10)1.01590 (18)0.17058 (16)0.0255 (5)
H41B0.57181.05970.09970.032*
H42B0.55711.06830.23080.032*
C43B0.64724 (11)0.9870 (2)0.19073 (18)0.0316 (5)
H43B0.66440.93170.13290.040*
H44B0.65070.94820.26390.040*
C44B0.68860 (10)1.09734 (19)0.18786 (17)0.0283 (5)
C45B0.71708 (12)1.1389 (2)0.08867 (18)0.0375 (6)
H45B0.71181.09490.02250.047*
C46B0.75285 (13)1.2424 (2)0.08407 (19)0.0418 (6)
H46B0.77171.26890.01500.052*
C47B0.76148 (12)1.3080 (2)0.17899 (18)0.0366 (5)
H47B0.78611.37950.17590.046*
C48B0.73374 (11)1.2681 (2)0.27793 (17)0.0346 (5)
H48B0.73941.31250.34380.043*
C49B0.69775 (11)1.1644 (2)0.28296 (17)0.0319 (5)
H49B0.67901.13850.35230.040*
C5B0.48059 (10)0.75290 (19)0.07229 (16)0.0261 (5)
H5B0.45390.73140.13590.033*
C6B0.47762 (10)0.69297 (19)0.02493 (16)0.0253 (4)
Cl6B0.42403 (3)0.57459 (5)0.03666 (5)0.04045 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0328 (10)0.0318 (11)0.0250 (9)0.0062 (8)0.0011 (7)0.0006 (8)
C2A0.0225 (11)0.0268 (12)0.0290 (11)0.0003 (9)0.0016 (8)0.0032 (9)
S21A0.0460 (4)0.0389 (4)0.0272 (3)0.0109 (3)0.0001 (2)0.0076 (2)
C22A0.0563 (17)0.0384 (16)0.0477 (15)0.0184 (13)0.0023 (12)0.0100 (12)
N3A0.0278 (9)0.0243 (10)0.0258 (9)0.0001 (8)0.0029 (7)0.0007 (7)
C4A0.0252 (11)0.0252 (12)0.0264 (11)0.0026 (9)0.0031 (8)0.0023 (8)
N41A0.0484 (12)0.0318 (12)0.0247 (10)0.0078 (9)0.0062 (8)0.0004 (8)
C42A0.0627 (17)0.0316 (14)0.0359 (12)0.0082 (12)0.0166 (11)0.0024 (10)
C43A0.075 (2)0.051 (2)0.101 (3)0.0199 (17)0.0514 (19)0.0166 (18)
C44A0.0384 (14)0.0403 (16)0.0530 (15)0.0068 (11)0.0198 (12)0.0084 (12)
C45A0.0490 (16)0.0533 (18)0.0410 (14)0.0028 (13)0.0044 (11)0.0019 (12)
C46A0.0365 (15)0.0479 (18)0.0662 (18)0.0072 (13)0.0041 (12)0.0122 (14)
C47A0.0532 (17)0.0352 (16)0.0720 (19)0.0007 (13)0.0295 (14)0.0049 (14)
C48A0.065 (2)0.067 (2)0.0470 (16)0.0172 (17)0.0070 (14)0.0080 (15)
C49A0.0342 (15)0.065 (2)0.0606 (18)0.0013 (13)0.0011 (12)0.0179 (15)
C5A0.0275 (11)0.0319 (13)0.0247 (10)0.0021 (9)0.0022 (8)0.0020 (9)
C6A0.0275 (11)0.0288 (13)0.0301 (11)0.0052 (9)0.0009 (8)0.0036 (9)
Cl6A0.0730 (5)0.0579 (5)0.0343 (3)0.0420 (4)0.0042 (3)0.0065 (3)
N1B0.0293 (10)0.0245 (10)0.0248 (9)0.0022 (8)0.0030 (7)0.0024 (7)
C2B0.0234 (10)0.0226 (11)0.0205 (9)0.0007 (8)0.0008 (7)0.0006 (8)
S21B0.0357 (3)0.0351 (3)0.0211 (3)0.0090 (2)0.0072 (2)0.0040 (2)
C22B0.0374 (13)0.0338 (14)0.0280 (11)0.0099 (10)0.0063 (9)0.0010 (9)
N3B0.0244 (9)0.0224 (9)0.0185 (8)0.0004 (7)0.0002 (6)0.0014 (7)
C4B0.0228 (10)0.0241 (12)0.0203 (9)0.0026 (8)0.0006 (7)0.0031 (8)
N41B0.0289 (10)0.0273 (11)0.0172 (9)0.0027 (8)0.0022 (7)0.0005 (7)
C42B0.0315 (12)0.0211 (12)0.0237 (10)0.0004 (9)0.0002 (8)0.0033 (8)
C43B0.0313 (12)0.0269 (13)0.0370 (12)0.0002 (10)0.0069 (9)0.0032 (9)
C44B0.0260 (11)0.0273 (13)0.0317 (11)0.0044 (9)0.0046 (8)0.0002 (9)
C45B0.0475 (15)0.0383 (15)0.0266 (12)0.0071 (11)0.0009 (10)0.0070 (10)
C46B0.0532 (16)0.0440 (16)0.0275 (12)0.0163 (12)0.0072 (10)0.0030 (10)
C47B0.0400 (13)0.0308 (14)0.0388 (13)0.0078 (11)0.0011 (10)0.0012 (10)
C48B0.0436 (14)0.0323 (14)0.0281 (11)0.0013 (11)0.0054 (9)0.0084 (9)
C49B0.0360 (13)0.0345 (14)0.0251 (11)0.0019 (10)0.0020 (9)0.0004 (9)
C5B0.0302 (11)0.0262 (12)0.0215 (10)0.0019 (9)0.0035 (8)0.0037 (8)
C6B0.0256 (11)0.0223 (12)0.0278 (11)0.0030 (9)0.0019 (8)0.0007 (8)
Cl6B0.0442 (4)0.0359 (4)0.0406 (3)0.0188 (3)0.0075 (2)0.0082 (2)
Geometric parameters (Å, º) top
N1A—C2A1.334 (3)N1B—C6B1.341 (2)
N1A—C6A1.346 (3)N1B—C2B1.343 (3)
C2A—N3A1.329 (3)C2B—N3B1.325 (2)
C2A—S21A1.757 (2)C2B—S21B1.7551 (19)
S21A—C22A1.790 (3)S21B—C22B1.791 (2)
C22A—H21A0.9800C22B—H21B0.9800
C22A—H22A0.9800C22B—H22B0.9800
C22A—H23A0.9800C22B—H23B0.9800
N3A—C4A1.345 (3)N3B—C4B1.353 (2)
C4A—N41A1.338 (3)C4B—N41B1.342 (3)
C4A—C5A1.406 (3)C4B—C5B1.401 (3)
N41A—C42A1.453 (3)N41B—C42B1.446 (3)
N41A—H4A0.87 (3)N41B—H4B0.82 (2)
C42A—C43A1.462 (4)C42B—C43B1.527 (3)
C42A—H41A0.9900C42B—H41B0.9900
C42A—H42A0.9900C42B—H42B0.9900
C43A—C44A1.512 (4)C43B—C44B1.503 (3)
C43A—H43A0.9900C43B—H43B0.9900
C43A—H44A0.9900C43B—H44B0.9900
C44A—C49A1.379 (4)C44B—C45B1.388 (3)
C44A—C45A1.377 (4)C44B—C49B1.393 (3)
C45A—C46A1.378 (4)C45B—C46B1.377 (3)
C45A—H45A0.9500C45B—H45B0.9500
C46A—C47A1.367 (4)C46B—C47B1.381 (3)
C46A—H46A0.9500C46B—H46B0.9500
C47A—C48A1.369 (4)C47B—C48B1.374 (3)
C47A—H47A0.9500C47B—H47B0.9500
C48A—C49A1.373 (4)C48B—C49B1.381 (3)
C48A—H48A0.9500C48B—H48B0.9500
C49A—H49A0.9500C49B—H49B0.9500
C5A—C6A1.353 (3)C5B—C6B1.357 (3)
C5A—H5A0.9500C5B—H5B0.9500
C6A—Cl6A1.732 (2)C6B—Cl6B1.730 (2)
C2A—N1A—C6A113.19 (17)C6B—N1B—C2B113.57 (16)
N3A—C2A—N1A128.47 (18)N3B—C2B—N1B128.21 (17)
N3A—C2A—S21A119.11 (16)N3B—C2B—S21B119.07 (15)
N1A—C2A—S21A112.42 (15)N1B—C2B—S21B112.71 (14)
C2A—S21A—C22A102.31 (11)C2B—S21B—C22B101.87 (10)
S21A—C22A—H21A109.5S21B—C22B—H21B109.5
S21A—C22A—H22A109.5S21B—C22B—H22B109.5
H21A—C22A—H22A109.5H21B—C22B—H22B109.5
S21A—C22A—H23A109.5S21B—C22B—H23B109.5
H21A—C22A—H23A109.5H21B—C22B—H23B109.5
H22A—C22A—H23A109.5H22B—C22B—H23B109.5
C2A—N3A—C4A115.68 (17)C2B—N3B—C4B115.97 (17)
N41A—C4A—N3A118.81 (19)N41B—C4B—N3B117.73 (18)
N41A—C4A—C5A119.59 (19)N41B—C4B—C5B121.33 (17)
N3A—C4A—C5A121.60 (17)N3B—C4B—C5B120.93 (17)
C4A—N41A—C42A126.2 (2)C4B—N41B—C42B123.49 (17)
C4A—N41A—H4A113.8 (17)C4B—N41B—H4B116.0 (18)
C42A—N41A—H4A119.9 (17)C42B—N41B—H4B118.8 (17)
N41A—C42A—C43A110.5 (2)N41B—C42B—C43B114.05 (18)
N41A—C42A—H41A109.6N41B—C42B—H41B108.7
C43A—C42A—H41A109.6C43B—C42B—H41B108.7
N41A—C42A—H42A109.6N41B—C42B—H42B108.7
C43A—C42A—H42A109.6C43B—C42B—H42B108.7
H41A—C42A—H42A108.1H41B—C42B—H42B107.6
C42A—C43A—C44A115.1 (3)C44B—C43B—C42B110.34 (18)
C42A—C43A—H43A108.5C44B—C43B—H43B109.6
C44A—C43A—H43A108.5C42B—C43B—H43B109.6
C42A—C43A—H44A108.5C44B—C43B—H44B109.6
C44A—C43A—H44A108.5C42B—C43B—H44B109.6
H43A—C43A—H44A107.5H43B—C43B—H44B108.1
C49A—C44A—C45A117.7 (3)C45B—C44B—C49B117.4 (2)
C49A—C44A—C43A120.8 (3)C45B—C44B—C43B120.86 (19)
C45A—C44A—C43A121.5 (3)C49B—C44B—C43B121.74 (19)
C46A—C45A—C44A121.4 (3)C46B—C45B—C44B121.5 (2)
C46A—C45A—H45A119.3C46B—C45B—H45B119.3
C44A—C45A—H45A119.3C44B—C45B—H45B119.3
C47A—C46A—C45A120.0 (3)C47B—C46B—C45B120.5 (2)
C47A—C46A—H46A120.0C47B—C46B—H46B119.7
C45A—C46A—H46A120.0C45B—C46B—H46B119.7
C48A—C47A—C46A119.3 (3)C48B—C47B—C46B118.8 (2)
C48A—C47A—H47A120.3C48B—C47B—H47B120.6
C46A—C47A—H47A120.3C46B—C47B—H47B120.6
C47A—C48A—C49A120.6 (3)C47B—C48B—C49B120.9 (2)
C47A—C48A—H48A119.7C47B—C48B—H48B119.5
C49A—C48A—H48A119.7C49B—C48B—H48B119.5
C44A—C49A—C48A121.0 (3)C48B—C49B—C44B120.9 (2)
C44A—C49A—H49A119.5C48B—C49B—H49B119.5
C48A—C49A—H49A119.5C44B—C49B—H49B119.5
C6A—C5A—C4A115.68 (19)C6B—C5B—C4B116.59 (17)
C6A—C5A—H5A122.2C6B—C5B—H5B121.7
C4A—C5A—H5A122.2C4B—C5B—H5B121.7
N1A—C6A—C5A125.4 (2)N1B—C6B—C5B124.72 (19)
N1A—C6A—Cl6A114.87 (15)N1B—C6B—Cl6B114.84 (15)
C5A—C6A—Cl6A119.75 (16)C5B—C6B—Cl6B120.43 (15)
C6A—N1A—C2A—N3A0.9 (3)C6B—N1B—C2B—N3B0.1 (3)
C6A—N1A—C2A—S21A179.34 (15)C6B—N1B—C2B—S21B178.91 (15)
N3A—C2A—S21A—C22A0.6 (2)N3B—C2B—S21B—C22B0.72 (19)
N1A—C2A—S21A—C22A179.61 (17)N1B—C2B—S21B—C22B178.21 (16)
N1A—C2A—N3A—C4A0.5 (3)N1B—C2B—N3B—C4B0.5 (3)
S21A—C2A—N3A—C4A179.67 (15)S21B—C2B—N3B—C4B179.23 (14)
C2A—N3A—C4A—N41A179.43 (19)C2B—N3B—C4B—N41B179.54 (18)
C2A—N3A—C4A—C5A0.2 (3)C2B—N3B—C4B—C5B0.8 (3)
N3A—C4A—N41A—C42A0.7 (3)N3B—C4B—N41B—C42B1.5 (3)
C5A—C4A—N41A—C42A179.6 (2)C5B—C4B—N41B—C42B177.22 (19)
C4A—N41A—C42A—C43A133.7 (3)C4B—N41B—C42B—C43B82.9 (2)
N41A—C42A—C43A—C44A170.4 (3)N41B—C42B—C43B—C44B176.75 (16)
C42A—C43A—C44A—C49A104.5 (3)C42B—C43B—C44B—C45B88.5 (2)
C42A—C43A—C44A—C45A78.0 (4)C42B—C43B—C44B—C49B88.9 (2)
C49A—C44A—C45A—C46A1.2 (4)C49B—C44B—C45B—C46B0.2 (4)
C43A—C44A—C45A—C46A176.4 (3)C43B—C44B—C45B—C46B177.4 (2)
C44A—C45A—C46A—C47A0.8 (4)C44B—C45B—C46B—C47B0.1 (4)
C45A—C46A—C47A—C48A0.2 (4)C45B—C46B—C47B—C48B0.0 (4)
C46A—C47A—C48A—C49A0.7 (4)C46B—C47B—C48B—C49B0.1 (4)
C45A—C44A—C49A—C48A0.6 (4)C47B—C48B—C49B—C44B0.0 (3)
C43A—C44A—C49A—C48A177.0 (3)C45B—C44B—C49B—C48B0.1 (3)
C47A—C48A—C49A—C44A0.3 (4)C43B—C44B—C49B—C48B177.4 (2)
N41A—C4A—C5A—C6A179.1 (2)N41B—C4B—C5B—C6B179.46 (19)
N3A—C4A—C5A—C6A0.6 (3)N3B—C4B—C5B—C6B0.8 (3)
C2A—N1A—C6A—C5A0.4 (3)C2B—N1B—C6B—C5B0.0 (3)
C2A—N1A—C6A—Cl6A179.84 (16)C2B—N1B—C6B—Cl6B179.23 (15)
C4A—C5A—C6A—N1A0.2 (3)C4B—C5B—C6B—N1B0.4 (3)
C4A—C5A—C6A—Cl6A179.15 (16)C4B—C5B—C6B—Cl6B179.51 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41A—H4A···N1Ai0.87 (3)2.14 (3)3.005 (3)171 (2)
N41B—H4B···N1Bii0.82 (2)2.24 (3)3.022 (2)161 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC26H28Cl2N6S2
Mr559.56
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)20.038 (4), 11.358 (2), 12.043 (2)
β (°) 92.03 (3)
V3)2739.3 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.921, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
23836, 6216, 4274
Rint0.083
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.123, 1.00
No. of reflections6216
No. of parameters335
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.44, 0.52

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41A—H4A···N1Ai0.87 (3)2.14 (3)3.005 (3)171 (2)
N41B—H4B···N1Bii0.82 (2)2.24 (3)3.022 (2)161 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2.
 

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