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In the crystal structure of pyrimeth­amine [2,4-di­amino-5-(p-chloro­phenyl)-6-ethyl­pyrimidine], C12H13ClN4, the asymmetric unit contains two crystallographically independent pyrimeth­amine molecules (A and B), differing in their conformations. The dihedral angle between the pyrimidine and the substituted phenyl plane is 74.4 (1)° in mol­ecule A and 82.4 (1)° in mol­ecule B. Molecule A is linked with mol­ecule B through a pair of N—H...N hydrogen bonds on one side and through another pair of N—H...N hydrogen bonds on the other side. Thus, there is a supramolecular ribbon, consisting of A and B molecules arranged in an alternating manner. Two such ribbons are connected centrosymmetrically through a pair of N—H...Cl bonds. These ABAB pairs and BABA interconnections lead to a supramolecular sheet-like structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011133/cv6122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011133/cv6122Isup2.hkl
Contains datablock I

CCDC reference: 193733

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.142
  • Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(2A) - H(21A) ? PLAT_420 Alert C D-H Without Acceptor N(2B) - H(21B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1997).

(I) top
Crystal data top
C12H13ClN4Z = 4
Mr = 248.71F(000) = 520
Triclinic, P1Dx = 1.313 Mg m3
a = 9.5854 (15) ÅMo Kα radiation, λ = 0.71069 Å
b = 10.8061 (17) ÅCell parameters from 25 reflections
c = 12.484 (2) Åθ = 10–15°
α = 79.059 (13)°µ = 0.29 mm1
β = 89.440 (15)°T = 293 K
γ = 82.372 (14)°Transparent block, colourless
V = 1258.2 (4) Å30.32 × 0.19 × 0.19 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
4035 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω–2θ scansh = 011
Absorption correction: ψ scan
(North et al., 1967)
k = 1212
Tmin = 0.936, Tmax = 0.974l = 1414
4724 measured reflections3 standard reflections every 60 min
4437 independent reflections intensity decay: 1%
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0673P)2 + 0.5352P]
where P = (Fo2 + 2Fc2)/3
4437 reflections(Δ/σ)max < 0.001
376 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.40 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A0.85491 (9)1.01495 (7)0.40577 (5)0.0749 (3)
N1A0.7040 (2)0.78059 (16)0.16260 (14)0.0468 (6)
N2A0.6761 (3)0.8613 (2)0.34565 (16)0.0654 (8)
N3A0.7075 (2)1.00158 (16)0.23392 (13)0.0448 (5)
N4A0.7332 (2)1.14112 (18)0.12145 (16)0.0514 (7)
C2A0.6975 (2)0.8819 (2)0.24368 (16)0.0450 (7)
C4A0.7247 (2)1.02144 (19)0.13254 (16)0.0401 (6)
C5A0.7357 (2)0.92088 (19)0.04051 (15)0.0398 (6)
C6A0.7244 (2)0.80191 (19)0.06125 (16)0.0427 (6)
C7A0.7268 (3)0.6865 (2)0.02823 (18)0.0540 (7)
C8A0.5803 (4)0.6590 (3)0.0568 (3)0.0982 (14)
C9A0.7627 (2)0.94599 (19)0.07031 (16)0.0410 (6)
C10A0.6592 (3)1.0062 (2)0.12756 (18)0.0492 (7)
C11A0.6860 (3)1.0290 (2)0.23064 (19)0.0542 (8)
C12A0.8179 (3)0.9908 (2)0.27554 (17)0.0513 (7)
C13A0.9231 (3)0.9313 (3)0.2211 (2)0.0636 (9)
C14A0.8946 (3)0.9099 (3)0.1184 (2)0.0594 (8)
Cl1B0.13130 (10)0.69014 (8)0.94533 (5)0.0808 (3)
N1B0.28215 (19)0.41356 (16)0.38322 (14)0.0448 (5)
N2B0.3091 (3)0.4859 (2)0.20104 (16)0.0566 (7)
N3B0.2677 (2)0.63546 (16)0.30910 (13)0.0473 (6)
N4B0.2279 (3)0.78406 (19)0.41796 (18)0.0637 (8)
C2B0.2849 (2)0.51285 (19)0.30141 (16)0.0429 (6)
C4B0.2447 (2)0.6612 (2)0.40893 (17)0.0457 (6)
C5B0.2372 (2)0.56421 (19)0.50154 (16)0.0430 (6)
C6B0.2569 (2)0.4414 (2)0.48342 (16)0.0447 (7)
C7B0.2570 (3)0.3283 (2)0.57432 (19)0.0592 (8)
C8B0.4039 (5)0.2729 (4)0.6113 (3)0.1170 (17)
C9B0.2115 (2)0.5973 (2)0.61144 (16)0.0445 (6)
C10B0.3198 (3)0.6231 (2)0.67235 (18)0.0503 (7)
C11B0.2957 (3)0.6532 (2)0.77487 (19)0.0551 (8)
C12B0.1624 (3)0.6566 (2)0.81498 (18)0.0548 (8)
C13B0.0531 (3)0.6340 (3)0.7562 (2)0.0719 (10)
C14B0.0785 (3)0.6049 (3)0.6538 (2)0.0675 (10)
H10A0.567 (3)1.030 (2)0.0970 (18)0.043 (6)*
H11A0.608 (3)1.067 (3)0.270 (2)0.071 (8)*
H13A1.014 (4)0.902 (3)0.253 (3)0.094 (10)*
H14A0.971 (4)0.864 (3)0.086 (3)0.093 (10)*
H21A0.686 (3)0.923 (3)0.398 (3)0.081 (9)*
H22A0.683 (3)0.787 (3)0.356 (2)0.056 (7)*
H41A0.748 (3)1.156 (3)0.055 (2)0.059 (7)*
H42A0.724 (3)1.205 (3)0.177 (2)0.066 (8)*
H71A0.773860.700800.092370.079 (4)*
H72A0.779500.613680.004660.079 (4)*
H81A0.532310.648630.007420.158 (8)*
H82A0.584450.582420.110770.158 (8)*
H83A0.530310.728500.085240.158 (8)*
H10B0.416 (3)0.614 (3)0.645 (2)0.067 (8)*
H11B0.372 (3)0.678 (3)0.816 (3)0.078 (9)*
H13B0.046 (4)0.639 (4)0.786 (3)0.107 (12)*
H14B0.005 (4)0.585 (3)0.613 (3)0.085 (9)*
H21B0.298 (4)0.549 (4)0.148 (3)0.090 (11)*
H22B0.310 (3)0.413 (3)0.194 (2)0.057 (7)*
H41B0.215 (3)0.799 (3)0.482 (3)0.069 (8)*
H42B0.249 (3)0.847 (3)0.364 (3)0.078 (9)*
H71B0.204710.353840.635230.079 (4)*
H72B0.210420.264260.549490.079 (4)*
H81B0.455970.248320.550890.158 (8)*
H82B0.401220.199630.668050.158 (8)*
H83B0.448790.335170.638650.158 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.1154 (6)0.0750 (5)0.0389 (3)0.0104 (4)0.0114 (3)0.0233 (3)
N1A0.0700 (12)0.0371 (9)0.0348 (9)0.0113 (8)0.0009 (8)0.0081 (7)
N2A0.123 (2)0.0440 (12)0.0326 (10)0.0187 (12)0.0023 (10)0.0103 (9)
N3A0.0648 (11)0.0378 (9)0.0323 (8)0.0090 (8)0.0009 (7)0.0068 (7)
N4A0.0826 (14)0.0367 (10)0.0361 (10)0.0119 (9)0.0008 (9)0.0072 (8)
C2A0.0622 (13)0.0391 (11)0.0353 (10)0.0111 (9)0.0000 (9)0.0077 (8)
C4A0.0486 (11)0.0372 (10)0.0354 (10)0.0077 (8)0.0019 (8)0.0077 (8)
C5A0.0482 (11)0.0385 (10)0.0323 (10)0.0064 (8)0.0004 (8)0.0055 (8)
C6A0.0545 (12)0.0389 (11)0.0351 (10)0.0084 (9)0.0006 (8)0.0062 (8)
C7A0.0812 (16)0.0399 (11)0.0392 (11)0.0077 (11)0.0034 (10)0.0036 (9)
C8A0.096 (2)0.082 (2)0.098 (3)0.0177 (18)0.0197 (19)0.0331 (19)
C9A0.0517 (11)0.0394 (10)0.0330 (10)0.0098 (8)0.0022 (8)0.0075 (8)
C10A0.0531 (13)0.0522 (13)0.0420 (11)0.0038 (10)0.0001 (9)0.0104 (9)
C11A0.0694 (15)0.0548 (14)0.0403 (11)0.0062 (11)0.0087 (10)0.0158 (10)
C12A0.0760 (15)0.0472 (12)0.0340 (10)0.0150 (11)0.0010 (10)0.0110 (9)
C13A0.0608 (15)0.0843 (19)0.0477 (13)0.0029 (13)0.0098 (11)0.0220 (12)
C14A0.0563 (13)0.0796 (18)0.0447 (12)0.0004 (12)0.0021 (10)0.0239 (12)
Cl1B0.1161 (6)0.0898 (5)0.0447 (4)0.0161 (4)0.0118 (3)0.0326 (3)
N1B0.0602 (10)0.0395 (9)0.0368 (9)0.0134 (8)0.0019 (7)0.0082 (7)
N2B0.0970 (16)0.0412 (11)0.0361 (10)0.0212 (11)0.0086 (9)0.0110 (8)
N3B0.0710 (12)0.0386 (9)0.0333 (9)0.0108 (8)0.0012 (8)0.0073 (7)
N4B0.1132 (19)0.0397 (11)0.0375 (10)0.0060 (11)0.0049 (11)0.0090 (9)
C2B0.0531 (11)0.0411 (11)0.0368 (10)0.0140 (9)0.0013 (8)0.0080 (8)
C4B0.0603 (12)0.0390 (11)0.0379 (10)0.0074 (9)0.0015 (9)0.0069 (8)
C5B0.0519 (11)0.0424 (11)0.0356 (10)0.0085 (9)0.0003 (8)0.0078 (8)
C6B0.0545 (12)0.0446 (12)0.0365 (10)0.0146 (9)0.0003 (8)0.0056 (8)
C7B0.0901 (18)0.0467 (13)0.0422 (12)0.0227 (12)0.0049 (11)0.0026 (10)
C8B0.119 (3)0.095 (3)0.114 (3)0.024 (2)0.038 (2)0.047 (2)
C9B0.0565 (12)0.0420 (11)0.0349 (10)0.0065 (9)0.0005 (9)0.0074 (8)
C10B0.0554 (13)0.0550 (13)0.0411 (11)0.0074 (10)0.0001 (9)0.0105 (9)
C11B0.0674 (15)0.0573 (14)0.0430 (12)0.0077 (11)0.0095 (10)0.0151 (10)
C12B0.0761 (16)0.0520 (13)0.0377 (11)0.0068 (11)0.0024 (10)0.0137 (9)
C13B0.0654 (16)0.103 (2)0.0560 (15)0.0155 (15)0.0139 (12)0.0345 (15)
C14B0.0578 (15)0.103 (2)0.0513 (14)0.0205 (14)0.0032 (11)0.0322 (14)
Geometric parameters (Å, º) top
Cl1A—C12A1.742 (2)C12A—C13A1.368 (4)
Cl1B—C12B1.748 (2)C13A—C14A1.381 (4)
N1A—C6A1.349 (3)C7A—H71A0.9701
N1A—C2A1.338 (3)C7A—H72A0.9698
N2A—C2A1.355 (3)C8A—H82A0.9594
N3A—C2A1.338 (3)C8A—H83A0.9602
N3A—C4A1.339 (3)C8A—H81A0.9602
N4A—C4A1.340 (3)C10A—H10A0.95 (3)
N2A—H21A0.85 (4)C11A—H11A0.98 (3)
N2A—H22A0.83 (3)C13A—H13A0.95 (4)
N4A—H42A0.88 (3)C14A—H14A0.96 (4)
N4A—H41A0.89 (3)C4B—C5B1.414 (3)
N1B—C2B1.336 (3)C5B—C9B1.492 (3)
N1B—C6B1.353 (3)C5B—C6B1.376 (3)
N2B—C2B1.350 (3)C6B—C7B1.502 (3)
N3B—C4B1.338 (3)C7B—C8B1.496 (5)
N3B—C2B1.335 (3)C9B—C10B1.381 (3)
N4B—C4B1.342 (3)C9B—C14B1.374 (3)
N2B—H22B0.81 (3)C10B—C11B1.389 (3)
N2B—H21B0.85 (4)C11B—C12B1.366 (4)
N4B—H41B0.85 (4)C12B—C13B1.359 (4)
N4B—H42B0.90 (3)C13B—C14B1.385 (4)
C4A—C5A1.418 (3)C7B—H71B0.9701
C5A—C9A1.491 (3)C7B—H72B0.9698
C5A—C6A1.377 (3)C8B—H81B0.9602
C6A—C7A1.506 (3)C8B—H82B0.9600
C7A—C8A1.499 (5)C8B—H83B0.9599
C9A—C14A1.381 (3)C10B—H10B0.98 (3)
C9A—C10A1.382 (3)C11B—H11B0.99 (3)
C10A—C11A1.388 (3)C13B—H13B1.02 (4)
C11A—C12A1.368 (4)C14B—H14B0.94 (4)
Cl1A···Cl1Ai3.6024 (12)C9A···H41A2.49 (3)
Cl1A···N4Bii3.393 (2)C9B···H71B2.6004
Cl1B···N4Aii3.472 (2)C9B···H41B2.46 (3)
Cl1A···H21Aiii3.01 (3)C10A···H41A2.73 (3)
Cl1A···H72Biv3.1085C10B···H41B2.85 (4)
Cl1A···H41Bii2.67 (3)C11A···H82Biv2.7828
Cl1B···H21Biii3.04 (4)C11A···H11Bii3.08 (3)
Cl1B···H41Aii2.72 (3)C11B···H82Aiv2.7779
Cl1B···H14Av3.07 (4)C14A···H71A2.7443
N1A···N2Bvi3.027 (3)C14B···H71B2.8705
N1B···N2Avi3.068 (3)H10A···C4Avii2.94 (3)
N2A···N1Bvi3.068 (3)H10A···C5Avii2.95 (3)
N2B···N1Avi3.027 (3)H10B···C2Biv3.03 (3)
N3A···N4Bvii3.060 (3)H10B···N1Biv2.89 (3)
N3B···N4Avii3.027 (3)H11A···C2Avii2.92 (3)
N4A···N3Bvii3.027 (3)H11A···N2Avii2.93 (3)
N4A···Cl1Bii3.472 (2)H11B···C11Aii3.08 (3)
N4A···C10A3.287 (3)H13A···H42Bxii2.60 (5)
N4B···Cl1Aii3.393 (2)H13A···N4Ax2.95 (4)
N4B···N3Avii3.060 (3)H13A···C4Ax3.04 (4)
N4B···C10B3.382 (3)H13A···N4Bxii2.91 (4)
N1A···H22Bvi2.22 (3)H13B···N1Av2.80 (4)
N1A···H81A2.8296H14A···Cl1Bviii3.07 (4)
N1A···H13Bviii2.80 (4)H14A···N4Ax2.87 (4)
N1B···H81B2.8645H14B···N1Bix2.75 (4)
N1B···H14Bix2.75 (4)H14B···C6Bix2.87 (4)
N1B···H22Avi2.24 (3)H21A···Cl1Axiii3.01 (3)
N1B···H10Biv2.89 (3)H21B···Cl1Bxiii3.04 (4)
N2A···H11Avii2.93 (3)H22A···N1Bvi2.24 (3)
N3A···H42Bvii2.16 (3)H22B···N1Avi2.22 (3)
N3B···H83Biv2.8729H41A···C10A2.73 (3)
N3B···H42Avii2.16 (3)H41A···Cl1Bii2.72 (3)
N4A···H14Ax2.87 (4)H41A···C9A2.49 (3)
N4A···H83Avii2.8007H41B···C9B2.46 (3)
N4A···H13Ax2.95 (4)H41B···C10B2.85 (4)
N4B···H13Axi2.91 (4)H41B···Cl1Aii2.67 (3)
C4B···C8Biv3.531 (5)H42A···N3Bvii2.16 (3)
C7A···C14A3.432 (4)H42A···C4Bvii3.01 (3)
C7B···C14B3.547 (4)H42A···H42Bvii2.51 (4)
C8B···C4Biv3.531 (5)H42B···H13Axi2.60 (5)
C10A···N4A3.287 (3)H42B···N3Avii2.16 (3)
C10B···N4B3.382 (3)H42B···C4Avii2.99 (4)
C11A···C11Bii3.450 (3)H42B···H42Avii2.51 (4)
C11B···C11Aii3.450 (3)H71A···C9A2.5992
C14A···C7A3.432 (4)H71A···C14A2.7443
C14B···C7B3.547 (4)H71B···C9B2.6004
C2A···H11Avii2.92 (3)H71B···C14B2.8705
C2B···H10Biv3.03 (3)H72B···Cl1Aiv3.1085
C4A···H13Ax3.04 (4)H81A···N1A2.8296
C4A···H10Avii2.94 (3)H81B···N1B2.8645
C4A···H42Bvii2.99 (4)H82A···C11Biv2.7779
C4B···H42Avii3.01 (3)H82B···C11Aiv2.7828
C4B···H83Biv2.9957H83A···N4Avii2.8007
C5A···H10Avii2.95 (3)H83B···N3Biv2.8729
C6B···H14Bix2.87 (4)H83B···C4Biv2.9957
C9A···H71A2.5992
C2A—N1A—C6A116.25 (18)C9A—C10A—H10A119.5 (14)
C2A—N3A—C4A116.38 (17)C11A—C10A—H10A119.1 (14)
H21A—N2A—H22A121 (3)C10A—C11A—H11A118.4 (16)
C2A—N2A—H21A116 (2)C12A—C11A—H11A122.7 (16)
C2A—N2A—H22A119.1 (17)C12A—C13A—H13A122 (2)
H41A—N4A—H42A119 (3)C14A—C13A—H13A119 (2)
C4A—N4A—H41A118 (2)C13A—C14A—H14A115 (2)
C4A—N4A—H42A122.4 (19)C9A—C14A—H14A123 (2)
C2B—N1B—C6B116.09 (18)N1B—C2B—N2B116.46 (19)
C2B—N3B—C4B116.47 (17)N1B—C2B—N3B126.64 (18)
C2B—N2B—H21B116 (3)N2B—C2B—N3B116.89 (19)
C2B—N2B—H22B117.8 (18)N3B—C4B—N4B117.1 (2)
H21B—N2B—H22B124 (3)N3B—C4B—C5B122.03 (19)
C4B—N4B—H41B116 (2)N4B—C4B—C5B120.8 (2)
H41B—N4B—H42B119 (3)C4B—C5B—C9B120.22 (19)
C4B—N4B—H42B123 (2)C4B—C5B—C6B116.17 (18)
N1A—C2A—N3A126.55 (18)C6B—C5B—C9B123.61 (18)
N1A—C2A—N2A116.6 (2)N1B—C6B—C5B122.57 (19)
N2A—C2A—N3A116.88 (19)N1B—C6B—C7B115.13 (19)
N4A—C4A—C5A120.95 (18)C5B—C6B—C7B122.26 (18)
N3A—C4A—C5A122.03 (19)C6B—C7B—C8B111.1 (2)
N3A—C4A—N4A117.01 (18)C10B—C9B—C14B118.3 (2)
C4A—C5A—C6A116.06 (17)C5B—C9B—C14B120.63 (19)
C4A—C5A—C9A120.30 (18)C5B—C9B—C10B121.08 (19)
C6A—C5A—C9A123.61 (18)C9B—C10B—C11B120.9 (2)
N1A—C6A—C5A122.71 (18)C10B—C11B—C12B118.8 (2)
C5A—C6A—C7A122.47 (18)Cl1B—C12B—C11B119.3 (2)
N1A—C6A—C7A114.76 (18)Cl1B—C12B—C13B119.0 (2)
C6A—C7A—C8A110.9 (2)C11B—C12B—C13B121.7 (2)
C10A—C9A—C14A117.9 (2)C12B—C13B—C14B118.9 (3)
C5A—C9A—C10A121.98 (19)C9B—C14B—C13B121.4 (3)
C5A—C9A—C14A120.07 (19)C6B—C7B—H71B109.41
C9A—C10A—C11A121.3 (2)C6B—C7B—H72B109.41
C10A—C11A—C12A118.8 (2)C8B—C7B—H71B109.42
C11A—C12A—C13A121.5 (2)C8B—C7B—H72B109.45
Cl1A—C12A—C13A118.3 (2)H71B—C7B—H72B108.03
Cl1A—C12A—C11A120.21 (19)C7B—C8B—H81B109.46
C12A—C13A—C14A118.9 (3)C7B—C8B—H82B109.47
C9A—C14A—C13A121.6 (3)C7B—C8B—H83B109.49
C6A—C7A—H71A109.44H81B—C8B—H82B109.46
C6A—C7A—H72A109.46H81B—C8B—H83B109.46
C8A—C7A—H71A109.46H82B—C8B—H83B109.48
C8A—C7A—H72A109.47C9B—C10B—H10B119.3 (16)
H71A—C7A—H72A108.06C11B—C10B—H10B119.6 (16)
C7A—C8A—H82A109.49C10B—C11B—H11B120.7 (19)
C7A—C8A—H83A109.45C12B—C11B—H11B120.3 (19)
H81A—C8A—H82A109.50C12B—C13B—H13B121 (2)
H81A—C8A—H83A109.44C14B—C13B—H13B120 (2)
H82A—C8A—H83A109.50C9B—C14B—H14B118 (2)
C7A—C8A—H81A109.45C13B—C14B—H14B120 (2)
C6A—N1A—C2A—N2A179.6 (2)C5A—C9A—C14A—C13A179.8 (3)
C6A—N1A—C2A—N3A0.9 (3)C10A—C9A—C14A—C13A0.8 (4)
C2A—N1A—C6A—C5A1.1 (3)C9A—C10A—C11A—C12A0.1 (3)
C2A—N1A—C6A—C7A178.3 (2)C10A—C11A—C12A—C13A0.1 (4)
C4A—N3A—C2A—N1A0.5 (3)C10A—C11A—C12A—Cl1A178.79 (18)
C4A—N3A—C2A—N2A178.2 (2)C11A—C12A—C13A—C14A0.1 (4)
C2A—N3A—C4A—N4A179.23 (19)Cl1A—C12A—C13A—C14A179.1 (2)
C2A—N3A—C4A—C5A1.7 (3)C12A—C13A—C14A—C9A0.6 (4)
C2B—N1B—C6B—C7B178.90 (19)N3B—C4B—C5B—C9B179.93 (18)
C2B—N1B—C6B—C5B1.0 (3)N4B—C4B—C5B—C6B179.6 (2)
C6B—N1B—C2B—N3B1.2 (3)N4B—C4B—C5B—C9B0.5 (3)
C6B—N1B—C2B—N2B179.6 (2)N3B—C4B—C5B—C6B0.9 (3)
C4B—N3B—C2B—N1B0.4 (3)C4B—C5B—C6B—N1B0.0 (3)
C2B—N3B—C4B—C5B0.7 (3)C4B—C5B—C6B—C7B177.8 (2)
C2B—N3B—C4B—N4B179.7 (2)C9B—C5B—C6B—C7B1.2 (3)
C4B—N3B—C2B—N2B179.6 (2)C4B—C5B—C9B—C10B81.2 (3)
N3A—C4A—C5A—C9A176.62 (19)C9B—C5B—C6B—N1B178.99 (18)
N3A—C4A—C5A—C6A1.4 (3)C4B—C5B—C9B—C14B97.7 (3)
N4A—C4A—C5A—C9A2.4 (3)C6B—C5B—C9B—C10B97.8 (3)
N4A—C4A—C5A—C6A179.52 (19)C6B—C5B—C9B—C14B83.3 (3)
C4A—C5A—C9A—C10A74.7 (3)N1B—C6B—C7B—C8B80.7 (3)
C4A—C5A—C6A—N1A0.0 (3)C5B—C6B—C7B—C8B97.2 (3)
C9A—C5A—C6A—C7A5.0 (3)C5B—C9B—C10B—C11B179.6 (2)
C4A—C5A—C9A—C14A104.7 (3)C14B—C9B—C10B—C11B1.4 (3)
C4A—C5A—C6A—C7A177.0 (2)C10B—C9B—C14B—C13B1.8 (4)
C6A—C5A—C9A—C10A107.4 (3)C5B—C9B—C14B—C13B179.2 (3)
C9A—C5A—C6A—N1A178.02 (19)C9B—C10B—C11B—C12B0.2 (3)
C6A—C5A—C9A—C14A73.3 (3)C10B—C11B—C12B—Cl1B178.30 (17)
N1A—C6A—C7A—C8A79.4 (3)C10B—C11B—C12B—C13B1.4 (4)
C5A—C6A—C7A—C8A97.8 (3)C11B—C12B—C13B—C14B1.0 (4)
C14A—C9A—C10A—C11A0.5 (3)Cl1B—C12B—C13B—C14B178.7 (2)
C5A—C9A—C10A—C11A179.9 (2)C12B—C13B—C14B—C9B0.7 (5)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x, y, z+1; (iv) x+1, y+1, z+1; (v) x1, y, z+1; (vi) x+1, y+1, z; (vii) x+1, y+2, z; (viii) x+1, y, z1; (ix) x, y+1, z+1; (x) x+2, y+2, z; (xi) x1, y, z; (xii) x+1, y, z; (xiii) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H22A···N1Bvi0.83 (3)2.24 (3)3.068 (3)176 (3)
N2B—H22B···N1Avi0.81 (3)2.22 (3)3.027 (3)174 (3)
N4A—H41A···Cl1Bii0.89 (3)2.72 (3)3.472 (2)143 (2)
N4B—H41B···Cl1Aii0.85 (4)2.67 (3)3.393 (2)143 (3)
N4A—H42A···N3Bvii0.88 (3)2.16 (3)3.027 (3)172 (3)
N4B—H42B···N3Avii0.90 (3)2.16 (3)3.060 (3)178 (3)
Symmetry codes: (ii) x+1, y+2, z+1; (vi) x+1, y+1, z; (vii) x+1, y+2, z.
 

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