Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020670/na6114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020670/na6114Isup2.hkl |
CCDC reference: 180544
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.150
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(51) - H(52) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
To a solution of 0.3 g (0.867 mmol) of compound 5-N-(benzotriazol-1-ylmethyl)amino-1-phenyl-3-tert-butylpyrazole in 15 ml of absolute methanol were added 20–30 mg of p-toluensulfonic acid, and was stirred at room temperature for 1 h (TLC control). The solvent was removed under reduced pressure, the residue was re-dissolved in ethyl acetate, washed with a 10% NaOH solution and dried with anhydrous sodium sulfate. The solution was concentrated and purified by column chromatography on silica gel an a mixture 80:20 (hexane–ethyl acetate) as eluent, yielding 0.27 g (90%) of title compound as white crystals, which resulted suitable for X-ray diffraction. M.p. 397 K.
H atoms attached to C atoms were included at calculated positions and treated as riding atoms with C—H 0.95–0.99 Å., The H atoms attached to the N atoms were included at positions based on those found on a difference map were initially DFIXED to a value of 0.87 Å and then allowed to ride on the parent N atom.
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C20H22N6 | Dx = 1.303 Mg m−3 |
Mr = 346.44 | Melting point: 397K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.465 (3) Å | Cell parameters from 4002 reflections |
b = 15.135 (3) Å | θ = 3.1–27.5° |
c = 9.1558 (18) Å | µ = 0.08 mm−1 |
β = 108.86 (3)° | T = 100 K |
V = 1765.8 (6) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.10 mm |
F(000) = 736 |
KappaCCD diffractometer | 4002 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −17→17 |
Tmin = 0.988, Tmax = 0.992 | k = −19→19 |
10902 measured reflections | l = −11→11 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0599P)2] where P = (Fo2 + 2Fc2)/3 |
4002 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.27 e Å−3 |
2 restraints | Δρmin = −0.39 e Å−3 |
C20H22N6 | V = 1765.8 (6) Å3 |
Mr = 346.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.465 (3) Å | µ = 0.08 mm−1 |
b = 15.135 (3) Å | T = 100 K |
c = 9.1558 (18) Å | 0.15 × 0.15 × 0.10 mm |
β = 108.86 (3)° |
KappaCCD diffractometer | 4002 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 2136 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.992 | Rint = 0.077 |
10902 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 2 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.27 e Å−3 |
4002 reflections | Δρmin = −0.39 e Å−3 |
244 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.22730 (13) | 0.03333 (12) | 0.69269 (19) | 0.0172 (4) | |
C11 | 0.27550 (16) | 0.07547 (15) | 0.8375 (2) | 0.0177 (5) | |
C12 | 0.35843 (17) | 0.03735 (15) | 0.9512 (2) | 0.0208 (5) | |
C13 | 0.40553 (17) | 0.08237 (16) | 1.0868 (2) | 0.0237 (6) | |
C14 | 0.37268 (18) | 0.16631 (16) | 1.1102 (3) | 0.0239 (6) | |
C15 | 0.28992 (18) | 0.20431 (15) | 0.9951 (3) | 0.0245 (6) | |
C16 | 0.24104 (18) | 0.15984 (15) | 0.8595 (3) | 0.0208 (5) | |
N2 | 0.17458 (13) | 0.08611 (12) | 0.56890 (19) | 0.0189 (4) | |
C3 | 0.13923 (15) | 0.03215 (14) | 0.4493 (2) | 0.0161 (5) | |
C31 | 0.07902 (17) | 0.07128 (15) | 0.2936 (2) | 0.0198 (5) | |
C311 | 0.15601 (18) | 0.08983 (17) | 0.2048 (3) | 0.0268 (6) | |
C312 | −0.00729 (17) | 0.00835 (16) | 0.1993 (3) | 0.0256 (6) | |
C313 | 0.02710 (18) | 0.15873 (15) | 0.3159 (3) | 0.0260 (6) | |
C4 | 0.16794 (16) | −0.05694 (15) | 0.4945 (2) | 0.0169 (5) | |
C41 | 0.15031 (18) | −0.13986 (15) | 0.4001 (3) | 0.0210 (5) | |
N41 | 0.21879 (14) | −0.14572 (12) | 0.3031 (2) | 0.0211 (5) | |
N42 | 0.17663 (16) | −0.16008 (13) | 0.1497 (2) | 0.0256 (5) | |
N43 | 0.25208 (16) | −0.16117 (13) | 0.0880 (2) | 0.0270 (5) | |
C43A | 0.34558 (19) | −0.14769 (15) | 0.2043 (3) | 0.0224 (6) | |
C44 | 0.44820 (19) | −0.14220 (15) | 0.1991 (3) | 0.0270 (6) | |
C45 | 0.5256 (2) | −0.12518 (16) | 0.3343 (3) | 0.0298 (6) | |
C46 | 0.50479 (19) | −0.11511 (16) | 0.4743 (3) | 0.0289 (6) | |
C47 | 0.40509 (18) | −0.12115 (16) | 0.4821 (3) | 0.0247 (6) | |
C47A | 0.32551 (17) | −0.13719 (15) | 0.3428 (3) | 0.0204 (5) | |
C5 | 0.22172 (16) | −0.05349 (15) | 0.6496 (2) | 0.0182 (5) | |
N51 | 0.26680 (16) | −0.12086 (13) | 0.7537 (2) | 0.0230 (5) | |
H12 | 0.3828 | −0.0197 | 0.9359 | 0.025* | |
H13 | 0.4615 | 0.0554 | 1.1655 | 0.028* | |
H14 | 0.4062 | 0.1973 | 1.2034 | 0.029* | |
H15 | 0.2666 | 0.2618 | 1.0099 | 0.029* | |
H16 | 0.1843 | 0.1864 | 0.7816 | 0.025* | |
H31A | 0.2093 | 0.1321 | 0.2629 | 0.040* | |
H31B | 0.1177 | 0.1146 | 0.1033 | 0.040* | |
H31C | 0.1902 | 0.0346 | 0.1916 | 0.040* | |
H31D | 0.0246 | −0.0410 | 0.1612 | 0.038* | |
H31E | −0.0553 | 0.0403 | 0.1117 | 0.038* | |
H31F | −0.0463 | −0.0145 | 0.2649 | 0.038* | |
H31G | −0.0224 | 0.1473 | 0.3721 | 0.039* | |
H31H | −0.0105 | 0.1844 | 0.2148 | 0.039* | |
H31I | 0.0812 | 0.2001 | 0.3750 | 0.039* | |
H41A | 0.1634 | −0.1915 | 0.4700 | 0.025* | |
H41B | 0.0761 | −0.1421 | 0.3330 | 0.025* | |
H44 | 0.4631 | −0.1500 | 0.1053 | 0.032* | |
H45 | 0.5959 | −0.1199 | 0.3342 | 0.036* | |
H46 | 0.5614 | −0.1038 | 0.5660 | 0.035* | |
H47 | 0.3909 | −0.1148 | 0.5767 | 0.030* | |
H51 | 0.2579 | −0.1161 | 0.8434 | 0.028* | |
H52 | 0.2428 | −0.1708 | 0.7092 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0158 (10) | 0.0177 (11) | 0.0168 (9) | 0.0002 (8) | 0.0036 (8) | −0.0008 (9) |
C11 | 0.0158 (12) | 0.0199 (12) | 0.0180 (12) | −0.0020 (10) | 0.0063 (9) | 0.0001 (10) |
C12 | 0.0193 (12) | 0.0207 (13) | 0.0202 (12) | 0.0008 (10) | 0.0036 (10) | −0.0025 (11) |
C13 | 0.0196 (12) | 0.0256 (14) | 0.0222 (13) | 0.0012 (10) | 0.0018 (10) | 0.0000 (11) |
C14 | 0.0238 (13) | 0.0238 (14) | 0.0209 (12) | −0.0047 (11) | 0.0028 (10) | −0.0026 (11) |
C15 | 0.0270 (13) | 0.0191 (13) | 0.0257 (13) | −0.0002 (11) | 0.0061 (11) | −0.0025 (11) |
C16 | 0.0170 (11) | 0.0220 (13) | 0.0203 (12) | 0.0005 (10) | 0.0019 (10) | −0.0020 (11) |
N2 | 0.0150 (9) | 0.0202 (11) | 0.0196 (10) | 0.0013 (8) | 0.0028 (8) | 0.0032 (9) |
C3 | 0.0104 (11) | 0.0200 (13) | 0.0188 (11) | −0.0023 (9) | 0.0058 (9) | −0.0019 (10) |
C31 | 0.0137 (11) | 0.0229 (13) | 0.0205 (12) | −0.0022 (10) | 0.0024 (9) | 0.0003 (10) |
C311 | 0.0228 (13) | 0.0313 (15) | 0.0263 (13) | −0.0045 (11) | 0.0082 (11) | 0.0035 (12) |
C312 | 0.0172 (12) | 0.0291 (14) | 0.0253 (12) | −0.0025 (11) | −0.0001 (10) | −0.0006 (11) |
C313 | 0.0210 (13) | 0.0241 (14) | 0.0278 (13) | 0.0017 (11) | 0.0007 (10) | 0.0041 (11) |
C4 | 0.0117 (11) | 0.0197 (12) | 0.0183 (11) | −0.0011 (9) | 0.0033 (9) | −0.0010 (10) |
C41 | 0.0196 (12) | 0.0212 (13) | 0.0213 (12) | −0.0016 (10) | 0.0052 (10) | −0.0004 (10) |
N41 | 0.0233 (11) | 0.0212 (11) | 0.0167 (10) | −0.0022 (9) | 0.0036 (9) | −0.0027 (8) |
N42 | 0.0327 (12) | 0.0234 (11) | 0.0187 (10) | −0.0011 (9) | 0.0056 (9) | −0.0027 (9) |
N43 | 0.0323 (12) | 0.0271 (12) | 0.0224 (11) | 0.0031 (10) | 0.0099 (10) | −0.0010 (9) |
C43A | 0.0285 (14) | 0.0171 (13) | 0.0215 (13) | 0.0042 (10) | 0.0077 (11) | 0.0019 (10) |
C44 | 0.0319 (15) | 0.0254 (14) | 0.0289 (14) | 0.0093 (11) | 0.0170 (12) | 0.0074 (11) |
C45 | 0.0232 (13) | 0.0302 (15) | 0.0390 (15) | 0.0080 (11) | 0.0141 (12) | 0.0115 (12) |
C46 | 0.0202 (13) | 0.0316 (15) | 0.0309 (14) | 0.0033 (11) | 0.0029 (11) | 0.0067 (12) |
C47 | 0.0220 (13) | 0.0283 (14) | 0.0238 (13) | 0.0040 (11) | 0.0075 (11) | 0.0008 (11) |
C47A | 0.0187 (12) | 0.0165 (12) | 0.0252 (13) | 0.0023 (10) | 0.0060 (10) | −0.0010 (10) |
C5 | 0.0135 (11) | 0.0187 (12) | 0.0222 (12) | 0.0010 (10) | 0.0055 (9) | 0.0009 (10) |
N51 | 0.0299 (12) | 0.0181 (11) | 0.0195 (11) | 0.0010 (9) | 0.0060 (10) | 0.0011 (9) |
N1—C5 | 1.367 (3) | C313—H31G | 0.9800 |
N1—N2 | 1.381 (2) | C313—H31H | 0.9800 |
N1—C11 | 1.425 (3) | C313—H31I | 0.9800 |
C11—C12 | 1.383 (3) | C4—C5 | 1.371 (3) |
C11—C16 | 1.395 (3) | C4—C41 | 1.499 (3) |
C12—C13 | 1.378 (3) | C41—N41 | 1.475 (3) |
C12—H12 | 0.9500 | C41—H41A | 0.9900 |
C13—C14 | 1.385 (3) | C41—H41B | 0.9900 |
C13—H13 | 0.9500 | N41—N42 | 1.352 (2) |
C14—C15 | 1.387 (3) | N41—C47A | 1.370 (3) |
C14—H14 | 0.9500 | N42—N43 | 1.312 (3) |
C15—C16 | 1.378 (3) | N43—C43A | 1.376 (3) |
C15—H15 | 0.9500 | C43A—C47A | 1.388 (3) |
C16—H16 | 0.9500 | C43A—C44 | 1.401 (3) |
N2—C3 | 1.325 (3) | C44—C45 | 1.361 (3) |
C3—C4 | 1.427 (3) | C44—H44 | 0.9500 |
C3—C31 | 1.514 (3) | C45—C46 | 1.405 (3) |
C31—C312 | 1.534 (3) | C45—H45 | 0.9500 |
C31—C311 | 1.536 (3) | C46—C47 | 1.370 (3) |
C31—C313 | 1.541 (3) | C46—H46 | 0.9500 |
C311—H31A | 0.9800 | C47—C47A | 1.396 (3) |
C311—H31B | 0.9800 | C47—H47 | 0.9500 |
C311—H31C | 0.9800 | C5—N51 | 1.394 (3) |
C312—H31D | 0.9800 | N51—H51 | 0.87 |
C312—H31E | 0.9800 | N51—H52 | 0.87 |
C312—H31F | 0.9800 | ||
C5—N1—N2 | 110.70 (16) | C31—C313—H31H | 109.5 |
C5—N1—C11 | 131.67 (18) | H31G—C313—H31H | 109.5 |
N2—N1—C11 | 117.62 (17) | C31—C313—H31I | 109.5 |
C12—C11—C16 | 119.9 (2) | H31G—C313—H31I | 109.5 |
C12—C11—N1 | 121.9 (2) | H31H—C313—H31I | 109.5 |
C16—C11—N1 | 118.13 (19) | C5—C4—C3 | 105.51 (19) |
C13—C12—C11 | 119.8 (2) | C5—C4—C41 | 124.2 (2) |
C13—C12—H12 | 120.1 | C3—C4—C41 | 130.30 (19) |
C11—C12—H12 | 120.1 | N41—C41—C4 | 112.59 (18) |
C12—C13—C14 | 121.1 (2) | N41—C41—H41A | 109.1 |
C12—C13—H13 | 119.5 | C4—C41—H41A | 109.1 |
C14—C13—H13 | 119.5 | N41—C41—H41B | 109.1 |
C13—C14—C15 | 118.8 (2) | C4—C41—H41B | 109.1 |
C13—C14—H14 | 120.6 | H41A—C41—H41B | 107.8 |
C15—C14—H14 | 120.6 | N42—N41—C47A | 110.04 (19) |
C16—C15—C14 | 121.0 (2) | N42—N41—C41 | 120.06 (18) |
C16—C15—H15 | 119.5 | C47A—N41—C41 | 129.89 (19) |
C14—C15—H15 | 119.5 | N43—N42—N41 | 109.01 (18) |
C15—C16—C11 | 119.5 (2) | N42—N43—C43A | 107.89 (17) |
C15—C16—H16 | 120.2 | N43—C43A—C47A | 108.9 (2) |
C11—C16—H16 | 120.2 | N43—C43A—C44 | 130.4 (2) |
C3—N2—N1 | 105.89 (17) | C47A—C43A—C44 | 120.7 (2) |
N2—C3—C4 | 110.58 (18) | C45—C44—C43A | 117.0 (2) |
N2—C3—C31 | 118.49 (19) | C45—C44—H44 | 121.5 |
C4—C3—C31 | 130.92 (19) | C43A—C44—H44 | 121.5 |
C3—C31—C312 | 111.37 (19) | C44—C45—C46 | 122.1 (2) |
C3—C31—C311 | 108.79 (18) | C44—C45—H45 | 119.0 |
C312—C31—C311 | 109.52 (18) | C46—C45—H45 | 119.0 |
C3—C31—C313 | 109.81 (18) | C47—C46—C45 | 121.8 (2) |
C312—C31—C313 | 108.31 (18) | C47—C46—H46 | 119.1 |
C311—C31—C313 | 109.0 (2) | C45—C46—H46 | 119.1 |
C31—C311—H31A | 109.5 | C46—C47—C47A | 116.1 (2) |
C31—C311—H31B | 109.5 | C46—C47—H47 | 122.0 |
H31A—C311—H31B | 109.5 | C47A—C47—H47 | 122.0 |
C31—C311—H31C | 109.5 | N41—C47A—C43A | 104.1 (2) |
H31A—C311—H31C | 109.5 | N41—C47A—C47 | 133.5 (2) |
H31B—C311—H31C | 109.5 | C43A—C47A—C47 | 122.4 (2) |
C31—C312—H31D | 109.5 | N1—C5—C4 | 107.27 (19) |
C31—C312—H31E | 109.5 | N1—C5—N51 | 122.33 (19) |
H31D—C312—H31E | 109.5 | C4—C5—N51 | 130.4 (2) |
C31—C312—H31F | 109.5 | C5—N51—H51 | 114.9 |
H31D—C312—H31F | 109.5 | C5—N51—H52 | 107.6 |
H31E—C312—H31F | 109.5 | H51—N51—H52 | 112.0 |
C31—C313—H31G | 109.5 | ||
C5—N1—C11—C12 | 24.1 (3) | C4—C41—N41—C47A | 52.1 (3) |
N2—N1—C11—C12 | −156.6 (2) | C47A—N41—N42—N43 | 0.0 (2) |
C5—N1—C11—C16 | −159.8 (2) | C41—N41—N42—N43 | 178.92 (18) |
N2—N1—C11—C16 | 19.6 (3) | N41—N42—N43—C43A | 0.3 (2) |
C16—C11—C12—C13 | 1.0 (3) | N42—N43—C43A—C47A | −0.5 (3) |
N1—C11—C12—C13 | 177.1 (2) | N42—N43—C43A—C44 | −179.3 (2) |
C11—C12—C13—C14 | −1.4 (3) | N43—C43A—C44—C45 | 177.8 (2) |
C12—C13—C14—C15 | 0.9 (4) | C47A—C43A—C44—C45 | −0.8 (3) |
C13—C14—C15—C16 | −0.1 (4) | C43A—C44—C45—C46 | 1.2 (4) |
C14—C15—C16—C11 | −0.2 (3) | C44—C45—C46—C47 | −0.6 (4) |
C12—C11—C16—C15 | −0.2 (3) | C45—C46—C47—C47A | −0.5 (4) |
N1—C11—C16—C15 | −176.5 (2) | N42—N41—C47A—C43A | −0.3 (2) |
C5—N1—N2—C3 | −1.7 (2) | C41—N41—C47A—C43A | −179.1 (2) |
C11—N1—N2—C3 | 178.84 (17) | N42—N41—C47A—C47 | 179.2 (2) |
N1—N2—C3—C4 | 0.5 (2) | C41—N41—C47A—C47 | 0.4 (4) |
N1—N2—C3—C31 | −178.85 (17) | N43—C43A—C47A—N41 | 0.5 (2) |
N2—C3—C31—C312 | −145.9 (2) | C44—C43A—C47A—N41 | 179.4 (2) |
C4—C3—C31—C312 | 34.9 (3) | N43—C43A—C47A—C47 | −179.1 (2) |
N2—C3—C31—C311 | 93.3 (2) | C44—C43A—C47A—C47 | −0.2 (3) |
C4—C3—C31—C311 | −85.9 (3) | C46—C47—C47A—N41 | −178.6 (2) |
N2—C3—C31—C313 | −26.0 (3) | C46—C47—C47A—C43A | 0.8 (3) |
C4—C3—C31—C313 | 154.8 (2) | N2—N1—C5—C4 | 2.2 (2) |
N2—C3—C4—C5 | 0.8 (2) | C11—N1—C5—C4 | −178.4 (2) |
C31—C3—C4—C5 | −180.0 (2) | N2—N1—C5—N51 | −178.71 (19) |
N2—C3—C4—C41 | −177.0 (2) | C11—N1—C5—N51 | 0.7 (3) |
C31—C3—C4—C41 | 2.3 (4) | C3—C4—C5—N1 | −1.8 (2) |
C5—C4—C41—N41 | −104.1 (2) | C41—C4—C5—N1 | 176.19 (19) |
C3—C4—C41—N41 | 73.3 (3) | C3—C4—C5—N51 | 179.2 (2) |
C4—C41—N41—N42 | −126.6 (2) | C41—C4—C5—N51 | −2.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N51—H51···N43i | 0.87 | 2.37 | 3.190 (3) | 158 |
Symmetry code: (i) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H22N6 |
Mr | 346.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.465 (3), 15.135 (3), 9.1558 (18) |
β (°) | 108.86 (3) |
V (Å3) | 1765.8 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.15 × 0.15 × 0.10 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.988, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10902, 4002, 2136 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.150, 0.95 |
No. of reflections | 4002 |
No. of parameters | 244 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.39 |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2001), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N51—H51···N43i | 0.87 | 2.37 | 3.190 (3) | 158 |
Symmetry code: (i) x, y, z+1. |
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The title compound, (I), was obtained by acid catalyzed rearragement from 5-N-(benzotriazol-1-ylmethyl)amino-1-phenyl-3-tert-butylpyrazole.
The main supramolecular stuctural feature is a hydrogen bond, N51–H51···N43, 3.190 Å, which links the molecules by unit translations along the c axis forming C(8) chains (Bernstein et al., 1995). H52 does not form a hydrogen bond. Details of the hydrogen bonding are given in Table 1. There are no weak C–H hydrogen bonds nor is there any π–π base-stacking. Examination of the structure with PLATON (Spek, 2001) showed that there were no solvent-accessible voids in the crystal lattice.