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In the crystal structure of pyrimethamine [2,4-diamino-5-(
p-chlorophenyl)-6-ethylpyrimidine], C
12H
13ClN
4, 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
CCDC reference: 193733
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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).
Crystal data top
C12H13ClN4 | Z = 4 |
Mr = 248.71 | F(000) = 520 |
Triclinic, P1 | Dx = 1.313 Mg m−3 |
a = 9.5854 (15) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 10.8061 (17) Å | Cell parameters from 25 reflections |
c = 12.484 (2) Å | θ = 10–15° |
α = 79.059 (13)° | µ = 0.29 mm−1 |
β = 89.440 (15)° | T = 293 K |
γ = 82.372 (14)° | Transparent block, colourless |
V = 1258.2 (4) Å3 | 0.32 × 0.19 × 0.19 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 4035 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.3°, θmin = 1.7° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1967) | k = −12→12 |
Tmin = 0.936, Tmax = 0.974 | l = −14→14 |
4724 measured reflections | 3 standard reflections every 60 min |
4437 independent reflections | intensity decay: 1% |
Refinement top
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H 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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1A | 0.85491 (9) | 1.01495 (7) | 0.40577 (5) | 0.0749 (3) | |
N1A | 0.7040 (2) | 0.78059 (16) | −0.16260 (14) | 0.0468 (6) | |
N2A | 0.6761 (3) | 0.8613 (2) | −0.34565 (16) | 0.0654 (8) | |
N3A | 0.7075 (2) | 1.00158 (16) | −0.23392 (13) | 0.0448 (5) | |
N4A | 0.7332 (2) | 1.14112 (18) | −0.12145 (16) | 0.0514 (7) | |
C2A | 0.6975 (2) | 0.8819 (2) | −0.24368 (16) | 0.0450 (7) | |
C4A | 0.7247 (2) | 1.02144 (19) | −0.13254 (16) | 0.0401 (6) | |
C5A | 0.7357 (2) | 0.92088 (19) | −0.04051 (15) | 0.0398 (6) | |
C6A | 0.7244 (2) | 0.80191 (19) | −0.06125 (16) | 0.0427 (6) | |
C7A | 0.7268 (3) | 0.6865 (2) | 0.02823 (18) | 0.0540 (7) | |
C8A | 0.5803 (4) | 0.6590 (3) | 0.0568 (3) | 0.0982 (14) | |
C9A | 0.7627 (2) | 0.94599 (19) | 0.07031 (16) | 0.0410 (6) | |
C10A | 0.6592 (3) | 1.0062 (2) | 0.12756 (18) | 0.0492 (7) | |
C11A | 0.6860 (3) | 1.0290 (2) | 0.23064 (19) | 0.0542 (8) | |
C12A | 0.8179 (3) | 0.9908 (2) | 0.27554 (17) | 0.0513 (7) | |
C13A | 0.9231 (3) | 0.9313 (3) | 0.2211 (2) | 0.0636 (9) | |
C14A | 0.8946 (3) | 0.9099 (3) | 0.1184 (2) | 0.0594 (8) | |
Cl1B | 0.13130 (10) | 0.69014 (8) | 0.94533 (5) | 0.0808 (3) | |
N1B | 0.28215 (19) | 0.41356 (16) | 0.38322 (14) | 0.0448 (5) | |
N2B | 0.3091 (3) | 0.4859 (2) | 0.20104 (16) | 0.0566 (7) | |
N3B | 0.2677 (2) | 0.63546 (16) | 0.30910 (13) | 0.0473 (6) | |
N4B | 0.2279 (3) | 0.78406 (19) | 0.41796 (18) | 0.0637 (8) | |
C2B | 0.2849 (2) | 0.51285 (19) | 0.30141 (16) | 0.0429 (6) | |
C4B | 0.2447 (2) | 0.6612 (2) | 0.40893 (17) | 0.0457 (6) | |
C5B | 0.2372 (2) | 0.56421 (19) | 0.50154 (16) | 0.0430 (6) | |
C6B | 0.2569 (2) | 0.4414 (2) | 0.48342 (16) | 0.0447 (7) | |
C7B | 0.2570 (3) | 0.3283 (2) | 0.57432 (19) | 0.0592 (8) | |
C8B | 0.4039 (5) | 0.2729 (4) | 0.6113 (3) | 0.1170 (17) | |
C9B | 0.2115 (2) | 0.5973 (2) | 0.61144 (16) | 0.0445 (6) | |
C10B | 0.3198 (3) | 0.6231 (2) | 0.67235 (18) | 0.0503 (7) | |
C11B | 0.2957 (3) | 0.6532 (2) | 0.77487 (19) | 0.0551 (8) | |
C12B | 0.1624 (3) | 0.6566 (2) | 0.81498 (18) | 0.0548 (8) | |
C13B | 0.0531 (3) | 0.6340 (3) | 0.7562 (2) | 0.0719 (10) | |
C14B | 0.0785 (3) | 0.6049 (3) | 0.6538 (2) | 0.0675 (10) | |
H10A | 0.567 (3) | 1.030 (2) | 0.0970 (18) | 0.043 (6)* | |
H11A | 0.608 (3) | 1.067 (3) | 0.270 (2) | 0.071 (8)* | |
H13A | 1.014 (4) | 0.902 (3) | 0.253 (3) | 0.094 (10)* | |
H14A | 0.971 (4) | 0.864 (3) | 0.086 (3) | 0.093 (10)* | |
H21A | 0.686 (3) | 0.923 (3) | −0.398 (3) | 0.081 (9)* | |
H22A | 0.683 (3) | 0.787 (3) | −0.356 (2) | 0.056 (7)* | |
H41A | 0.748 (3) | 1.156 (3) | −0.055 (2) | 0.059 (7)* | |
H42A | 0.724 (3) | 1.205 (3) | −0.177 (2) | 0.066 (8)* | |
H71A | 0.77386 | 0.70080 | 0.09237 | 0.079 (4)* | |
H72A | 0.77950 | 0.61368 | 0.00466 | 0.079 (4)* | |
H81A | 0.53231 | 0.64863 | −0.00742 | 0.158 (8)* | |
H82A | 0.58445 | 0.58242 | 0.11077 | 0.158 (8)* | |
H83A | 0.53031 | 0.72850 | 0.08524 | 0.158 (8)* | |
H10B | 0.416 (3) | 0.614 (3) | 0.645 (2) | 0.067 (8)* | |
H11B | 0.372 (3) | 0.678 (3) | 0.816 (3) | 0.078 (9)* | |
H13B | −0.046 (4) | 0.639 (4) | 0.786 (3) | 0.107 (12)* | |
H14B | 0.005 (4) | 0.585 (3) | 0.613 (3) | 0.085 (9)* | |
H21B | 0.298 (4) | 0.549 (4) | 0.148 (3) | 0.090 (11)* | |
H22B | 0.310 (3) | 0.413 (3) | 0.194 (2) | 0.057 (7)* | |
H41B | 0.215 (3) | 0.799 (3) | 0.482 (3) | 0.069 (8)* | |
H42B | 0.249 (3) | 0.847 (3) | 0.364 (3) | 0.078 (9)* | |
H71B | 0.20471 | 0.35384 | 0.63523 | 0.079 (4)* | |
H72B | 0.21042 | 0.26426 | 0.54949 | 0.079 (4)* | |
H81B | 0.45597 | 0.24832 | 0.55089 | 0.158 (8)* | |
H82B | 0.40122 | 0.19963 | 0.66805 | 0.158 (8)* | |
H83B | 0.44879 | 0.33517 | 0.63865 | 0.158 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.1154 (6) | 0.0750 (5) | 0.0389 (3) | −0.0104 (4) | −0.0114 (3) | −0.0233 (3) |
N1A | 0.0700 (12) | 0.0371 (9) | 0.0348 (9) | −0.0113 (8) | 0.0009 (8) | −0.0081 (7) |
N2A | 0.123 (2) | 0.0440 (12) | 0.0326 (10) | −0.0187 (12) | −0.0023 (10) | −0.0103 (9) |
N3A | 0.0648 (11) | 0.0378 (9) | 0.0323 (8) | −0.0090 (8) | 0.0009 (7) | −0.0068 (7) |
N4A | 0.0826 (14) | 0.0367 (10) | 0.0361 (10) | −0.0119 (9) | −0.0008 (9) | −0.0072 (8) |
C2A | 0.0622 (13) | 0.0391 (11) | 0.0353 (10) | −0.0111 (9) | 0.0000 (9) | −0.0077 (8) |
C4A | 0.0486 (11) | 0.0372 (10) | 0.0354 (10) | −0.0077 (8) | 0.0019 (8) | −0.0077 (8) |
C5A | 0.0482 (11) | 0.0385 (10) | 0.0323 (10) | −0.0064 (8) | −0.0004 (8) | −0.0055 (8) |
C6A | 0.0545 (12) | 0.0389 (11) | 0.0351 (10) | −0.0084 (9) | 0.0006 (8) | −0.0062 (8) |
C7A | 0.0812 (16) | 0.0399 (11) | 0.0392 (11) | −0.0077 (11) | −0.0034 (10) | −0.0036 (9) |
C8A | 0.096 (2) | 0.082 (2) | 0.098 (3) | −0.0177 (18) | 0.0197 (19) | 0.0331 (19) |
C9A | 0.0517 (11) | 0.0394 (10) | 0.0330 (10) | −0.0098 (8) | 0.0022 (8) | −0.0075 (8) |
C10A | 0.0531 (13) | 0.0522 (13) | 0.0420 (11) | −0.0038 (10) | 0.0001 (9) | −0.0104 (9) |
C11A | 0.0694 (15) | 0.0548 (14) | 0.0403 (11) | −0.0062 (11) | 0.0087 (10) | −0.0158 (10) |
C12A | 0.0760 (15) | 0.0472 (12) | 0.0340 (10) | −0.0150 (11) | −0.0010 (10) | −0.0110 (9) |
C13A | 0.0608 (15) | 0.0843 (19) | 0.0477 (13) | −0.0029 (13) | −0.0098 (11) | −0.0220 (12) |
C14A | 0.0563 (13) | 0.0796 (18) | 0.0447 (12) | 0.0004 (12) | −0.0021 (10) | −0.0239 (12) |
Cl1B | 0.1161 (6) | 0.0898 (5) | 0.0447 (4) | −0.0161 (4) | 0.0118 (3) | −0.0326 (3) |
N1B | 0.0602 (10) | 0.0395 (9) | 0.0368 (9) | −0.0134 (8) | 0.0019 (7) | −0.0082 (7) |
N2B | 0.0970 (16) | 0.0412 (11) | 0.0361 (10) | −0.0212 (11) | 0.0086 (9) | −0.0110 (8) |
N3B | 0.0710 (12) | 0.0386 (9) | 0.0333 (9) | −0.0108 (8) | 0.0012 (8) | −0.0073 (7) |
N4B | 0.1132 (19) | 0.0397 (11) | 0.0375 (10) | −0.0060 (11) | 0.0049 (11) | −0.0090 (9) |
C2B | 0.0531 (11) | 0.0411 (11) | 0.0368 (10) | −0.0140 (9) | 0.0013 (8) | −0.0080 (8) |
C4B | 0.0603 (12) | 0.0390 (11) | 0.0379 (10) | −0.0074 (9) | −0.0015 (9) | −0.0069 (8) |
C5B | 0.0519 (11) | 0.0424 (11) | 0.0356 (10) | −0.0085 (9) | −0.0003 (8) | −0.0078 (8) |
C6B | 0.0545 (12) | 0.0446 (12) | 0.0365 (10) | −0.0146 (9) | 0.0003 (8) | −0.0056 (8) |
C7B | 0.0901 (18) | 0.0467 (13) | 0.0422 (12) | −0.0227 (12) | 0.0049 (11) | −0.0026 (10) |
C8B | 0.119 (3) | 0.095 (3) | 0.114 (3) | −0.024 (2) | −0.038 (2) | 0.047 (2) |
C9B | 0.0565 (12) | 0.0420 (11) | 0.0349 (10) | −0.0065 (9) | −0.0005 (9) | −0.0074 (8) |
C10B | 0.0554 (13) | 0.0550 (13) | 0.0411 (11) | −0.0074 (10) | 0.0001 (9) | −0.0105 (9) |
C11B | 0.0674 (15) | 0.0573 (14) | 0.0430 (12) | −0.0077 (11) | −0.0095 (10) | −0.0151 (10) |
C12B | 0.0761 (16) | 0.0520 (13) | 0.0377 (11) | −0.0068 (11) | 0.0024 (10) | −0.0137 (9) |
C13B | 0.0654 (16) | 0.103 (2) | 0.0560 (15) | −0.0155 (15) | 0.0139 (12) | −0.0345 (15) |
C14B | 0.0578 (15) | 0.103 (2) | 0.0513 (14) | −0.0205 (14) | 0.0032 (11) | −0.0322 (14) |
Geometric parameters (Å, º) top
Cl1A—C12A | 1.742 (2) | C12A—C13A | 1.368 (4) |
Cl1B—C12B | 1.748 (2) | C13A—C14A | 1.381 (4) |
N1A—C6A | 1.349 (3) | C7A—H71A | 0.9701 |
N1A—C2A | 1.338 (3) | C7A—H72A | 0.9698 |
N2A—C2A | 1.355 (3) | C8A—H82A | 0.9594 |
N3A—C2A | 1.338 (3) | C8A—H83A | 0.9602 |
N3A—C4A | 1.339 (3) | C8A—H81A | 0.9602 |
N4A—C4A | 1.340 (3) | C10A—H10A | 0.95 (3) |
N2A—H21A | 0.85 (4) | C11A—H11A | 0.98 (3) |
N2A—H22A | 0.83 (3) | C13A—H13A | 0.95 (4) |
N4A—H42A | 0.88 (3) | C14A—H14A | 0.96 (4) |
N4A—H41A | 0.89 (3) | C4B—C5B | 1.414 (3) |
N1B—C2B | 1.336 (3) | C5B—C9B | 1.492 (3) |
N1B—C6B | 1.353 (3) | C5B—C6B | 1.376 (3) |
N2B—C2B | 1.350 (3) | C6B—C7B | 1.502 (3) |
N3B—C4B | 1.338 (3) | C7B—C8B | 1.496 (5) |
N3B—C2B | 1.335 (3) | C9B—C10B | 1.381 (3) |
N4B—C4B | 1.342 (3) | C9B—C14B | 1.374 (3) |
N2B—H22B | 0.81 (3) | C10B—C11B | 1.389 (3) |
N2B—H21B | 0.85 (4) | C11B—C12B | 1.366 (4) |
N4B—H41B | 0.85 (4) | C12B—C13B | 1.359 (4) |
N4B—H42B | 0.90 (3) | C13B—C14B | 1.385 (4) |
C4A—C5A | 1.418 (3) | C7B—H71B | 0.9701 |
C5A—C9A | 1.491 (3) | C7B—H72B | 0.9698 |
C5A—C6A | 1.377 (3) | C8B—H81B | 0.9602 |
C6A—C7A | 1.506 (3) | C8B—H82B | 0.9600 |
C7A—C8A | 1.499 (5) | C8B—H83B | 0.9599 |
C9A—C14A | 1.381 (3) | C10B—H10B | 0.98 (3) |
C9A—C10A | 1.382 (3) | C11B—H11B | 0.99 (3) |
C10A—C11A | 1.388 (3) | C13B—H13B | 1.02 (4) |
C11A—C12A | 1.368 (4) | C14B—H14B | 0.94 (4) |
| | | |
Cl1A···Cl1Ai | 3.6024 (12) | C9A···H41A | 2.49 (3) |
Cl1A···N4Bii | 3.393 (2) | C9B···H71B | 2.6004 |
Cl1B···N4Aii | 3.472 (2) | C9B···H41B | 2.46 (3) |
Cl1A···H21Aiii | 3.01 (3) | C10A···H41A | 2.73 (3) |
Cl1A···H72Biv | 3.1085 | C10B···H41B | 2.85 (4) |
Cl1A···H41Bii | 2.67 (3) | C11A···H82Biv | 2.7828 |
Cl1B···H21Biii | 3.04 (4) | C11A···H11Bii | 3.08 (3) |
Cl1B···H41Aii | 2.72 (3) | C11B···H82Aiv | 2.7779 |
Cl1B···H14Av | 3.07 (4) | C14A···H71A | 2.7443 |
N1A···N2Bvi | 3.027 (3) | C14B···H71B | 2.8705 |
N1B···N2Avi | 3.068 (3) | H10A···C4Avii | 2.94 (3) |
N2A···N1Bvi | 3.068 (3) | H10A···C5Avii | 2.95 (3) |
N2B···N1Avi | 3.027 (3) | H10B···C2Biv | 3.03 (3) |
N3A···N4Bvii | 3.060 (3) | H10B···N1Biv | 2.89 (3) |
N3B···N4Avii | 3.027 (3) | H11A···C2Avii | 2.92 (3) |
N4A···N3Bvii | 3.027 (3) | H11A···N2Avii | 2.93 (3) |
N4A···Cl1Bii | 3.472 (2) | H11B···C11Aii | 3.08 (3) |
N4A···C10A | 3.287 (3) | H13A···H42Bxii | 2.60 (5) |
N4B···Cl1Aii | 3.393 (2) | H13A···N4Ax | 2.95 (4) |
N4B···N3Avii | 3.060 (3) | H13A···C4Ax | 3.04 (4) |
N4B···C10B | 3.382 (3) | H13A···N4Bxii | 2.91 (4) |
N1A···H22Bvi | 2.22 (3) | H13B···N1Av | 2.80 (4) |
N1A···H81A | 2.8296 | H14A···Cl1Bviii | 3.07 (4) |
N1A···H13Bviii | 2.80 (4) | H14A···N4Ax | 2.87 (4) |
N1B···H81B | 2.8645 | H14B···N1Bix | 2.75 (4) |
N1B···H14Bix | 2.75 (4) | H14B···C6Bix | 2.87 (4) |
N1B···H22Avi | 2.24 (3) | H21A···Cl1Axiii | 3.01 (3) |
N1B···H10Biv | 2.89 (3) | H21B···Cl1Bxiii | 3.04 (4) |
N2A···H11Avii | 2.93 (3) | H22A···N1Bvi | 2.24 (3) |
N3A···H42Bvii | 2.16 (3) | H22B···N1Avi | 2.22 (3) |
N3B···H83Biv | 2.8729 | H41A···C10A | 2.73 (3) |
N3B···H42Avii | 2.16 (3) | H41A···Cl1Bii | 2.72 (3) |
N4A···H14Ax | 2.87 (4) | H41A···C9A | 2.49 (3) |
N4A···H83Avii | 2.8007 | H41B···C9B | 2.46 (3) |
N4A···H13Ax | 2.95 (4) | H41B···C10B | 2.85 (4) |
N4B···H13Axi | 2.91 (4) | H41B···Cl1Aii | 2.67 (3) |
C4B···C8Biv | 3.531 (5) | H42A···N3Bvii | 2.16 (3) |
C7A···C14A | 3.432 (4) | H42A···C4Bvii | 3.01 (3) |
C7B···C14B | 3.547 (4) | H42A···H42Bvii | 2.51 (4) |
C8B···C4Biv | 3.531 (5) | H42B···H13Axi | 2.60 (5) |
C10A···N4A | 3.287 (3) | H42B···N3Avii | 2.16 (3) |
C10B···N4B | 3.382 (3) | H42B···C4Avii | 2.99 (4) |
C11A···C11Bii | 3.450 (3) | H42B···H42Avii | 2.51 (4) |
C11B···C11Aii | 3.450 (3) | H71A···C9A | 2.5992 |
C14A···C7A | 3.432 (4) | H71A···C14A | 2.7443 |
C14B···C7B | 3.547 (4) | H71B···C9B | 2.6004 |
C2A···H11Avii | 2.92 (3) | H71B···C14B | 2.8705 |
C2B···H10Biv | 3.03 (3) | H72B···Cl1Aiv | 3.1085 |
C4A···H13Ax | 3.04 (4) | H81A···N1A | 2.8296 |
C4A···H10Avii | 2.94 (3) | H81B···N1B | 2.8645 |
C4A···H42Bvii | 2.99 (4) | H82A···C11Biv | 2.7779 |
C4B···H42Avii | 3.01 (3) | H82B···C11Aiv | 2.7828 |
C4B···H83Biv | 2.9957 | H83A···N4Avii | 2.8007 |
C5A···H10Avii | 2.95 (3) | H83B···N3Biv | 2.8729 |
C6B···H14Bix | 2.87 (4) | H83B···C4Biv | 2.9957 |
C9A···H71A | 2.5992 | | |
| | | |
C2A—N1A—C6A | 116.25 (18) | C9A—C10A—H10A | 119.5 (14) |
C2A—N3A—C4A | 116.38 (17) | C11A—C10A—H10A | 119.1 (14) |
H21A—N2A—H22A | 121 (3) | C10A—C11A—H11A | 118.4 (16) |
C2A—N2A—H21A | 116 (2) | C12A—C11A—H11A | 122.7 (16) |
C2A—N2A—H22A | 119.1 (17) | C12A—C13A—H13A | 122 (2) |
H41A—N4A—H42A | 119 (3) | C14A—C13A—H13A | 119 (2) |
C4A—N4A—H41A | 118 (2) | C13A—C14A—H14A | 115 (2) |
C4A—N4A—H42A | 122.4 (19) | C9A—C14A—H14A | 123 (2) |
C2B—N1B—C6B | 116.09 (18) | N1B—C2B—N2B | 116.46 (19) |
C2B—N3B—C4B | 116.47 (17) | N1B—C2B—N3B | 126.64 (18) |
C2B—N2B—H21B | 116 (3) | N2B—C2B—N3B | 116.89 (19) |
C2B—N2B—H22B | 117.8 (18) | N3B—C4B—N4B | 117.1 (2) |
H21B—N2B—H22B | 124 (3) | N3B—C4B—C5B | 122.03 (19) |
C4B—N4B—H41B | 116 (2) | N4B—C4B—C5B | 120.8 (2) |
H41B—N4B—H42B | 119 (3) | C4B—C5B—C9B | 120.22 (19) |
C4B—N4B—H42B | 123 (2) | C4B—C5B—C6B | 116.17 (18) |
N1A—C2A—N3A | 126.55 (18) | C6B—C5B—C9B | 123.61 (18) |
N1A—C2A—N2A | 116.6 (2) | N1B—C6B—C5B | 122.57 (19) |
N2A—C2A—N3A | 116.88 (19) | N1B—C6B—C7B | 115.13 (19) |
N4A—C4A—C5A | 120.95 (18) | C5B—C6B—C7B | 122.26 (18) |
N3A—C4A—C5A | 122.03 (19) | C6B—C7B—C8B | 111.1 (2) |
N3A—C4A—N4A | 117.01 (18) | C10B—C9B—C14B | 118.3 (2) |
C4A—C5A—C6A | 116.06 (17) | C5B—C9B—C14B | 120.63 (19) |
C4A—C5A—C9A | 120.30 (18) | C5B—C9B—C10B | 121.08 (19) |
C6A—C5A—C9A | 123.61 (18) | C9B—C10B—C11B | 120.9 (2) |
N1A—C6A—C5A | 122.71 (18) | C10B—C11B—C12B | 118.8 (2) |
C5A—C6A—C7A | 122.47 (18) | Cl1B—C12B—C11B | 119.3 (2) |
N1A—C6A—C7A | 114.76 (18) | Cl1B—C12B—C13B | 119.0 (2) |
C6A—C7A—C8A | 110.9 (2) | C11B—C12B—C13B | 121.7 (2) |
C10A—C9A—C14A | 117.9 (2) | C12B—C13B—C14B | 118.9 (3) |
C5A—C9A—C10A | 121.98 (19) | C9B—C14B—C13B | 121.4 (3) |
C5A—C9A—C14A | 120.07 (19) | C6B—C7B—H71B | 109.41 |
C9A—C10A—C11A | 121.3 (2) | C6B—C7B—H72B | 109.41 |
C10A—C11A—C12A | 118.8 (2) | C8B—C7B—H71B | 109.42 |
C11A—C12A—C13A | 121.5 (2) | C8B—C7B—H72B | 109.45 |
Cl1A—C12A—C13A | 118.3 (2) | H71B—C7B—H72B | 108.03 |
Cl1A—C12A—C11A | 120.21 (19) | C7B—C8B—H81B | 109.46 |
C12A—C13A—C14A | 118.9 (3) | C7B—C8B—H82B | 109.47 |
C9A—C14A—C13A | 121.6 (3) | C7B—C8B—H83B | 109.49 |
C6A—C7A—H71A | 109.44 | H81B—C8B—H82B | 109.46 |
C6A—C7A—H72A | 109.46 | H81B—C8B—H83B | 109.46 |
C8A—C7A—H71A | 109.46 | H82B—C8B—H83B | 109.48 |
C8A—C7A—H72A | 109.47 | C9B—C10B—H10B | 119.3 (16) |
H71A—C7A—H72A | 108.06 | C11B—C10B—H10B | 119.6 (16) |
C7A—C8A—H82A | 109.49 | C10B—C11B—H11B | 120.7 (19) |
C7A—C8A—H83A | 109.45 | C12B—C11B—H11B | 120.3 (19) |
H81A—C8A—H82A | 109.50 | C12B—C13B—H13B | 121 (2) |
H81A—C8A—H83A | 109.44 | C14B—C13B—H13B | 120 (2) |
H82A—C8A—H83A | 109.50 | C9B—C14B—H14B | 118 (2) |
C7A—C8A—H81A | 109.45 | C13B—C14B—H14B | 120 (2) |
| | | |
C6A—N1A—C2A—N2A | −179.6 (2) | C5A—C9A—C14A—C13A | −179.8 (3) |
C6A—N1A—C2A—N3A | −0.9 (3) | C10A—C9A—C14A—C13A | 0.8 (4) |
C2A—N1A—C6A—C5A | 1.1 (3) | C9A—C10A—C11A—C12A | 0.1 (3) |
C2A—N1A—C6A—C7A | 178.3 (2) | C10A—C11A—C12A—C13A | 0.1 (4) |
C4A—N3A—C2A—N1A | −0.5 (3) | C10A—C11A—C12A—Cl1A | −178.79 (18) |
C4A—N3A—C2A—N2A | 178.2 (2) | C11A—C12A—C13A—C14A | 0.1 (4) |
C2A—N3A—C4A—N4A | −179.23 (19) | Cl1A—C12A—C13A—C14A | 179.1 (2) |
C2A—N3A—C4A—C5A | 1.7 (3) | C12A—C13A—C14A—C9A | −0.6 (4) |
C2B—N1B—C6B—C7B | −178.90 (19) | N3B—C4B—C5B—C9B | 179.93 (18) |
C2B—N1B—C6B—C5B | −1.0 (3) | N4B—C4B—C5B—C6B | −179.6 (2) |
C6B—N1B—C2B—N3B | 1.2 (3) | N4B—C4B—C5B—C9B | −0.5 (3) |
C6B—N1B—C2B—N2B | −179.6 (2) | N3B—C4B—C5B—C6B | 0.9 (3) |
C4B—N3B—C2B—N1B | −0.4 (3) | C4B—C5B—C6B—N1B | 0.0 (3) |
C2B—N3B—C4B—C5B | −0.7 (3) | C4B—C5B—C6B—C7B | 177.8 (2) |
C2B—N3B—C4B—N4B | 179.7 (2) | C9B—C5B—C6B—C7B | −1.2 (3) |
C4B—N3B—C2B—N2B | −179.6 (2) | C4B—C5B—C9B—C10B | −81.2 (3) |
N3A—C4A—C5A—C9A | 176.62 (19) | C9B—C5B—C6B—N1B | −178.99 (18) |
N3A—C4A—C5A—C6A | −1.4 (3) | C4B—C5B—C9B—C14B | 97.7 (3) |
N4A—C4A—C5A—C9A | −2.4 (3) | C6B—C5B—C9B—C10B | 97.8 (3) |
N4A—C4A—C5A—C6A | 179.52 (19) | C6B—C5B—C9B—C14B | −83.3 (3) |
C4A—C5A—C9A—C10A | 74.7 (3) | N1B—C6B—C7B—C8B | 80.7 (3) |
C4A—C5A—C6A—N1A | 0.0 (3) | C5B—C6B—C7B—C8B | −97.2 (3) |
C9A—C5A—C6A—C7A | 5.0 (3) | C5B—C9B—C10B—C11B | −179.6 (2) |
C4A—C5A—C9A—C14A | −104.7 (3) | C14B—C9B—C10B—C11B | 1.4 (3) |
C4A—C5A—C6A—C7A | −177.0 (2) | C10B—C9B—C14B—C13B | −1.8 (4) |
C6A—C5A—C9A—C10A | −107.4 (3) | C5B—C9B—C14B—C13B | 179.2 (3) |
C9A—C5A—C6A—N1A | −178.02 (19) | C9B—C10B—C11B—C12B | 0.2 (3) |
C6A—C5A—C9A—C14A | 73.3 (3) | C10B—C11B—C12B—Cl1B | 178.30 (17) |
N1A—C6A—C7A—C8A | −79.4 (3) | C10B—C11B—C12B—C13B | −1.4 (4) |
C5A—C6A—C7A—C8A | 97.8 (3) | C11B—C12B—C13B—C14B | 1.0 (4) |
C14A—C9A—C10A—C11A | −0.5 (3) | Cl1B—C12B—C13B—C14B | −178.7 (2) |
C5A—C9A—C10A—C11A | −179.9 (2) | C12B—C13B—C14B—C9B | 0.7 (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) x−1, y, z+1; (vi) −x+1, −y+1, −z; (vii) −x+1, −y+2, −z; (viii) x+1, y, z−1; (ix) −x, −y+1, −z+1; (x) −x+2, −y+2, −z; (xi) x−1, y, z; (xii) x+1, y, z; (xiii) x, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H22A···N1Bvi | 0.83 (3) | 2.24 (3) | 3.068 (3) | 176 (3) |
N2B—H22B···N1Avi | 0.81 (3) | 2.22 (3) | 3.027 (3) | 174 (3) |
N4A—H41A···Cl1Bii | 0.89 (3) | 2.72 (3) | 3.472 (2) | 143 (2) |
N4B—H41B···Cl1Aii | 0.85 (4) | 2.67 (3) | 3.393 (2) | 143 (3) |
N4A—H42A···N3Bvii | 0.88 (3) | 2.16 (3) | 3.027 (3) | 172 (3) |
N4B—H42B···N3Avii | 0.90 (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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