Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001909/na6198sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001909/na6198Isup2.hkl |
CCDC reference: 204722
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.135
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.45 From the CIF: _reflns_number_total 3762 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4088 Completeness (_total/calc) 92.03% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A mixture of 3-amino-5-(tert-butyl)-2-phenyl-2H-pyrazole (0.11 g, 0.512 mmol), p-methoxybenzaldehyde (0.07 g, 0.514 mmol) and ethanol (10 ml) was heated to reflux for 5 min. After cooling, the pale yellow solid which formed was filtered off and washed with ethanol (85% yield; m.p. 394 K). 1H NMR (300 MHz, CDCl3, p.p.m.): 1.39 (9H, s), 3.85 (3H, s), 6.20 (1H, s), 6.95 (2H, d, J = 9.0 Hz), 7.26 (1H, t, J = 9.0 Hz), 7.42 (2H, br t), 7.79 (4H, br d), 8.58 (1H, s, N═CH); 13C NMR (75 MHz, CDCl3, p.p.m.): 30.4, 32.5, 55.4, 89.7, 114.3, 124.1, 126.1, 128.4, 129.0, 130.8, 139.9, 150.4, 159.2 (N═CH), 162.1, 162.6; MS (70 eV): m/e (%) 333 (95), 318 (73), 291 (44), 77 (100), 51 (48), 41 (77). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in ethanol.
H atoms were treated as riding atoms, with C—H distances in the range 0.95–0.98 Å. The data shows a completness of 0.92 at τ of 27.50° and 0.933 at θ of 25.00°; examination of the data shows that data at high θ values is very weak or absent. The methyl atoms of the tert-butyl group, particularly C54, have higher displacement parameters than the other atoms in the structure, indicating a degree of rotational disorder in this group.
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, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C21H23N3O | F(000) = 712 |
Mr = 333.42 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0744 (3) Å | Cell parameters from 3762 reflections |
b = 6.2583 (2) Å | θ = 3.2–27.5° |
c = 28.9244 (9) Å | µ = 0.08 mm−1 |
β = 101.0410 (13)° | T = 120 K |
V = 1789.89 (10) Å3 | Block, brown |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Nonius KappaCCD diffractometer | 3762 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2710 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ϕ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) | h = −11→13 |
Tmin = 0.970, Tmax = 0.992 | k = −8→4 |
9156 measured reflections | l = −37→31 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.7158P] where P = (Fo2 + 2Fc2)/3 |
3762 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C21H23N3O | V = 1789.89 (10) Å3 |
Mr = 333.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0744 (3) Å | µ = 0.08 mm−1 |
b = 6.2583 (2) Å | T = 120 K |
c = 28.9244 (9) Å | 0.40 × 0.20 × 0.10 mm |
β = 101.0410 (13)° |
Nonius KappaCCD diffractometer | 3762 independent reflections |
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) | 2710 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.992 | Rint = 0.056 |
9156 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.46 e Å−3 |
3762 reflections | Δρmin = −0.33 e Å−3 |
230 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 | 0.21013 (14) | 0.6008 (2) | 0.17069 (5) | 0.0215 (3) | |
N2 | 0.32887 (13) | 0.5996 (2) | 0.15426 (5) | 0.0195 (3) | |
C21 | 0.43008 (17) | 0.7516 (3) | 0.17282 (6) | 0.0201 (4) | |
C22 | 0.56627 (17) | 0.7080 (3) | 0.17514 (6) | 0.0241 (4) | |
C23 | 0.66133 (18) | 0.8601 (3) | 0.19416 (7) | 0.0286 (4) | |
C24 | 0.62257 (18) | 1.0517 (3) | 0.21143 (7) | 0.0274 (4) | |
C25 | 0.48641 (18) | 1.0928 (3) | 0.20909 (6) | 0.0248 (4) | |
C26 | 0.38998 (18) | 0.9439 (3) | 0.18996 (6) | 0.0218 (4) | |
C3 | 0.33061 (17) | 0.4384 (3) | 0.12247 (6) | 0.0193 (4) | |
N3 | 0.43791 (14) | 0.4147 (2) | 0.09877 (5) | 0.0213 (3) | |
C37 | 0.46951 (17) | 0.2236 (3) | 0.08898 (6) | 0.0216 (4) | |
C31 | 0.57039 (16) | 0.1785 (3) | 0.06040 (6) | 0.0194 (4) | |
C32 | 0.62042 (17) | 0.3385 (3) | 0.03502 (6) | 0.0221 (4) | |
C33 | 0.71205 (17) | 0.2945 (3) | 0.00625 (6) | 0.0228 (4) | |
C34 | 0.75693 (16) | 0.0856 (3) | 0.00348 (6) | 0.0206 (4) | |
O34 | 0.84677 (12) | 0.0230 (2) | −0.02368 (4) | 0.0255 (3) | |
C341 | 0.90609 (19) | 0.1862 (3) | −0.04779 (7) | 0.0307 (5) | |
C35 | 0.70938 (17) | −0.0763 (3) | 0.02908 (6) | 0.0227 (4) | |
C36 | 0.61608 (17) | −0.0306 (3) | 0.05694 (6) | 0.0223 (4) | |
C4 | 0.20824 (17) | 0.3353 (3) | 0.11775 (6) | 0.0224 (4) | |
C5 | 0.13743 (17) | 0.4415 (3) | 0.14827 (6) | 0.0216 (4) | |
C51 | −0.00362 (18) | 0.4000 (3) | 0.15686 (7) | 0.0265 (4) | |
C52 | −0.0148 (2) | 0.4669 (4) | 0.20646 (8) | 0.0433 (6) | |
C53 | −0.1036 (2) | 0.5377 (4) | 0.12246 (8) | 0.0459 (6) | |
C54 | −0.0413 (3) | 0.1673 (4) | 0.14818 (14) | 0.0711 (10) | |
H22 | 0.5940 | 0.5759 | 0.1639 | 0.029* | |
H23 | 0.7546 | 0.8323 | 0.1953 | 0.034* | |
H24 | 0.6887 | 1.1539 | 0.2247 | 0.033* | |
H25 | 0.4590 | 1.2244 | 0.2207 | 0.030* | |
H26 | 0.2967 | 0.9728 | 0.1885 | 0.026* | |
H37 | 0.4254 | 0.1073 | 0.1008 | 0.026* | |
H32 | 0.5909 | 0.4815 | 0.0375 | 0.027* | |
H33 | 0.7438 | 0.4052 | −0.0113 | 0.027* | |
H34A | 0.8357 | 0.2541 | −0.0713 | 0.046* | |
H34B | 0.9745 | 0.1226 | −0.0635 | 0.046* | |
H34C | 0.9487 | 0.2936 | −0.0251 | 0.046* | |
H35 | 0.7412 | −0.2184 | 0.0274 | 0.027* | |
H36 | 0.5827 | −0.1421 | 0.0739 | 0.027* | |
H4 | 0.1779 | 0.2169 | 0.0980 | 0.027* | |
H52A | 0.0473 | 0.3810 | 0.2294 | 0.065* | |
H52B | −0.1077 | 0.4446 | 0.2110 | 0.065* | |
H52C | 0.0088 | 0.6184 | 0.2110 | 0.065* | |
H53A | −0.0808 | 0.6890 | 0.1279 | 0.069* | |
H53B | −0.1957 | 0.5122 | 0.1276 | 0.069* | |
H53C | −0.0981 | 0.4996 | 0.0900 | 0.069* | |
H54A | −0.0384 | 0.1306 | 0.1154 | 0.107* | |
H54B | −0.1327 | 0.1433 | 0.1540 | 0.107* | |
H54C | 0.0230 | 0.0775 | 0.1694 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0182 (7) | 0.0242 (8) | 0.0231 (8) | −0.0008 (6) | 0.0068 (6) | 0.0003 (6) |
N2 | 0.0180 (7) | 0.0210 (8) | 0.0203 (8) | −0.0005 (6) | 0.0053 (6) | −0.0015 (6) |
C21 | 0.0218 (9) | 0.0217 (9) | 0.0164 (8) | −0.0039 (7) | 0.0028 (6) | 0.0019 (7) |
C22 | 0.0229 (9) | 0.0263 (10) | 0.0234 (10) | −0.0006 (7) | 0.0056 (7) | −0.0033 (8) |
C23 | 0.0205 (9) | 0.0364 (11) | 0.0287 (10) | −0.0040 (8) | 0.0040 (7) | −0.0025 (9) |
C24 | 0.0289 (10) | 0.0307 (11) | 0.0225 (10) | −0.0103 (8) | 0.0045 (8) | −0.0033 (8) |
C25 | 0.0326 (10) | 0.0218 (9) | 0.0199 (9) | −0.0017 (8) | 0.0046 (7) | 0.0001 (7) |
C26 | 0.0228 (9) | 0.0234 (10) | 0.0191 (9) | 0.0017 (7) | 0.0034 (7) | 0.0020 (7) |
C3 | 0.0217 (9) | 0.0191 (9) | 0.0170 (9) | 0.0015 (7) | 0.0035 (7) | 0.0003 (7) |
N3 | 0.0204 (7) | 0.0239 (8) | 0.0194 (8) | 0.0007 (6) | 0.0029 (6) | −0.0021 (6) |
C37 | 0.0215 (9) | 0.0230 (9) | 0.0194 (9) | −0.0016 (7) | 0.0012 (7) | −0.0008 (7) |
C31 | 0.0194 (8) | 0.0220 (9) | 0.0161 (8) | −0.0008 (7) | 0.0014 (7) | −0.0025 (7) |
C32 | 0.0238 (9) | 0.0182 (9) | 0.0241 (10) | 0.0008 (7) | 0.0039 (7) | −0.0017 (7) |
C33 | 0.0237 (9) | 0.0224 (9) | 0.0221 (9) | −0.0032 (7) | 0.0040 (7) | 0.0014 (7) |
C34 | 0.0190 (8) | 0.0243 (9) | 0.0182 (9) | −0.0009 (7) | 0.0028 (7) | −0.0026 (7) |
O34 | 0.0283 (7) | 0.0251 (7) | 0.0264 (7) | 0.0021 (5) | 0.0130 (5) | −0.0005 (6) |
C341 | 0.0328 (10) | 0.0335 (11) | 0.0291 (11) | 0.0023 (8) | 0.0143 (8) | 0.0052 (9) |
C35 | 0.0250 (9) | 0.0183 (9) | 0.0247 (10) | 0.0017 (7) | 0.0042 (7) | −0.0020 (7) |
C36 | 0.0245 (9) | 0.0205 (9) | 0.0213 (9) | −0.0014 (7) | 0.0026 (7) | 0.0014 (7) |
C4 | 0.0231 (9) | 0.0202 (9) | 0.0239 (10) | −0.0013 (7) | 0.0044 (7) | −0.0014 (7) |
C5 | 0.0205 (9) | 0.0213 (9) | 0.0229 (9) | −0.0003 (7) | 0.0036 (7) | 0.0026 (7) |
C51 | 0.0226 (9) | 0.0272 (10) | 0.0316 (11) | −0.0041 (8) | 0.0101 (8) | −0.0020 (8) |
C52 | 0.0272 (11) | 0.0749 (17) | 0.0300 (12) | −0.0071 (11) | 0.0107 (9) | −0.0017 (11) |
C53 | 0.0223 (10) | 0.0754 (18) | 0.0394 (13) | −0.0031 (10) | 0.0044 (9) | 0.0060 (12) |
C54 | 0.0517 (16) | 0.0371 (14) | 0.140 (3) | −0.0178 (12) | 0.0583 (18) | −0.0176 (16) |
N1—C5 | 1.330 (2) | C33—H33 | 0.9500 |
N1—N2 | 1.369 (2) | C34—O34 | 1.365 (2) |
N2—C3 | 1.367 (2) | C34—C35 | 1.393 (2) |
N2—C21 | 1.422 (2) | O34—C341 | 1.430 (2) |
C21—C22 | 1.388 (2) | C341—H34A | 0.9800 |
C21—C26 | 1.391 (2) | C341—H34B | 0.9800 |
C22—C23 | 1.387 (2) | C341—H34C | 0.9800 |
C22—H22 | 0.9500 | C35—C36 | 1.380 (3) |
C23—C24 | 1.384 (3) | C35—H35 | 0.9500 |
C23—H23 | 0.9500 | C36—H36 | 0.9500 |
C24—C25 | 1.385 (3) | C4—C5 | 1.404 (2) |
C24—H24 | 0.9500 | C4—H4 | 0.9500 |
C25—C26 | 1.383 (2) | C5—C51 | 1.511 (2) |
C25—H25 | 0.9500 | C51—C54 | 1.513 (3) |
C26—H26 | 0.9500 | C51—C52 | 1.519 (3) |
C3—C4 | 1.375 (2) | C51—C53 | 1.537 (3) |
C3—N3 | 1.394 (2) | C52—H52A | 0.9800 |
N3—C37 | 1.283 (2) | C52—H52B | 0.9800 |
C37—C31 | 1.455 (2) | C52—H52C | 0.9800 |
C37—H37 | 0.9500 | C53—H53A | 0.9800 |
C31—C32 | 1.392 (2) | C53—H53B | 0.9800 |
C31—C36 | 1.397 (2) | C53—H53C | 0.9800 |
C32—C33 | 1.384 (3) | C54—H54A | 0.9800 |
C32—H32 | 0.9500 | C54—H54B | 0.9800 |
C33—C34 | 1.391 (2) | C54—H54C | 0.9800 |
C5—N1—N2 | 105.23 (14) | O34—C341—H34A | 109.5 |
C3—N2—N1 | 111.23 (13) | O34—C341—H34B | 109.5 |
C3—N2—C21 | 130.29 (14) | H34A—C341—H34B | 109.5 |
N1—N2—C21 | 118.43 (14) | O34—C341—H34C | 109.5 |
C22—C21—C26 | 120.33 (16) | H34A—C341—H34C | 109.5 |
C22—C21—N2 | 121.16 (15) | H34B—C341—H34C | 109.5 |
C26—C21—N2 | 118.49 (15) | C36—C35—C34 | 120.10 (16) |
C23—C22—C21 | 119.03 (17) | C36—C35—H35 | 119.9 |
C23—C22—H22 | 120.5 | C34—C35—H35 | 119.9 |
C21—C22—H22 | 120.5 | C35—C36—C31 | 120.44 (17) |
C24—C23—C22 | 121.11 (17) | C35—C36—H36 | 119.8 |
C24—C23—H23 | 119.4 | C31—C36—H36 | 119.8 |
C22—C23—H23 | 119.4 | C3—C4—C5 | 105.61 (16) |
C23—C24—C25 | 119.28 (17) | C3—C4—H4 | 127.2 |
C23—C24—H24 | 120.4 | C5—C4—H4 | 127.2 |
C25—C24—H24 | 120.4 | N1—C5—C4 | 111.28 (15) |
C26—C25—C24 | 120.49 (17) | N1—C5—C51 | 119.74 (16) |
C26—C25—H25 | 119.8 | C4—C5—C51 | 128.96 (16) |
C24—C25—H25 | 119.8 | C5—C51—C54 | 110.61 (16) |
C25—C26—C21 | 119.74 (16) | C5—C51—C52 | 110.49 (15) |
C25—C26—H26 | 120.1 | C54—C51—C52 | 111.1 (2) |
C21—C26—H26 | 120.1 | C5—C51—C53 | 108.49 (16) |
N2—C3—C4 | 106.64 (15) | C54—C51—C53 | 108.6 (2) |
N2—C3—N3 | 121.34 (15) | C52—C51—C53 | 107.38 (17) |
C4—C3—N3 | 131.76 (16) | C51—C52—H52A | 109.5 |
C37—N3—C3 | 117.14 (15) | C51—C52—H52B | 109.5 |
N3—C37—C31 | 122.41 (16) | H52A—C52—H52B | 109.5 |
N3—C37—H37 | 118.8 | C51—C52—H52C | 109.5 |
C31—C37—H37 | 118.8 | H52A—C52—H52C | 109.5 |
C32—C31—C36 | 118.58 (16) | H52B—C52—H52C | 109.5 |
C32—C31—C37 | 121.52 (16) | C51—C53—H53A | 109.5 |
C36—C31—C37 | 119.87 (16) | C51—C53—H53B | 109.5 |
C33—C32—C31 | 121.65 (16) | H53A—C53—H53B | 109.5 |
C33—C32—H32 | 119.2 | C51—C53—H53C | 109.5 |
C31—C32—H32 | 119.2 | H53A—C53—H53C | 109.5 |
C32—C33—C34 | 118.92 (16) | H53B—C53—H53C | 109.5 |
C32—C33—H33 | 120.5 | C51—C54—H54A | 109.5 |
C34—C33—H33 | 120.5 | C51—C54—H54B | 109.5 |
O34—C34—C33 | 124.19 (16) | H54A—C54—H54B | 109.5 |
O34—C34—C35 | 115.52 (15) | C51—C54—H54C | 109.5 |
C33—C34—C35 | 120.29 (16) | H54A—C54—H54C | 109.5 |
C34—O34—C341 | 117.44 (14) | H54B—C54—H54C | 109.5 |
C5—N1—N2—C3 | −1.01 (18) | C37—C31—C32—C33 | −177.22 (16) |
C5—N1—N2—C21 | −178.66 (14) | C31—C32—C33—C34 | −1.3 (3) |
C3—N2—C21—C22 | −25.9 (3) | C32—C33—C34—O34 | 179.87 (16) |
N1—N2—C21—C22 | 151.18 (16) | C32—C33—C34—C35 | 0.4 (3) |
C3—N2—C21—C26 | 155.84 (17) | C33—C34—O34—C341 | 5.1 (2) |
N1—N2—C21—C26 | −27.0 (2) | C35—C34—O34—C341 | −175.37 (15) |
C26—C21—C22—C23 | −0.9 (3) | O34—C34—C35—C36 | −178.71 (15) |
N2—C21—C22—C23 | −179.08 (16) | C33—C34—C35—C36 | 0.8 (3) |
C21—C22—C23—C24 | 1.1 (3) | C34—C35—C36—C31 | −1.2 (3) |
C22—C23—C24—C25 | −0.8 (3) | C32—C31—C36—C35 | 0.3 (2) |
C23—C24—C25—C26 | 0.4 (3) | C37—C31—C36—C35 | 178.49 (16) |
C24—C25—C26—C21 | −0.2 (3) | N2—C3—C4—C5 | −0.63 (19) |
C22—C21—C26—C25 | 0.5 (3) | N3—C3—C4—C5 | −174.66 (18) |
N2—C21—C26—C25 | 178.70 (15) | N2—N1—C5—C4 | 0.59 (19) |
N1—N2—C3—C4 | 1.04 (19) | N2—N1—C5—C51 | −178.14 (15) |
C21—N2—C3—C4 | 178.32 (16) | C3—C4—C5—N1 | 0.0 (2) |
N1—N2—C3—N3 | 175.83 (14) | C3—C4—C5—C51 | 178.60 (17) |
C21—N2—C3—N3 | −6.9 (3) | N1—C5—C51—C54 | −153.1 (2) |
N2—C3—N3—C37 | 146.59 (16) | C4—C5—C51—C54 | 28.4 (3) |
C4—C3—N3—C37 | −40.1 (3) | N1—C5—C51—C52 | −29.6 (2) |
C3—N3—C37—C31 | 173.83 (15) | C4—C5—C51—C52 | 151.9 (2) |
N3—C37—C31—C32 | −11.9 (3) | N1—C5—C51—C53 | 87.9 (2) |
N3—C37—C31—C36 | 170.00 (16) | C4—C5—C51—C53 | −90.6 (2) |
C36—C31—C32—C33 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O34i | 0.95 | 2.59 | 3.487 (2) | 157 |
C25—H25···Cg1ii | 0.95 | 2.73 | 3.472 (2) | 135 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H23N3O |
Mr | 333.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 10.0744 (3), 6.2583 (2), 28.9244 (9) |
β (°) | 101.0410 (13) |
V (Å3) | 1789.89 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO–SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.970, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9156, 3762, 2710 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.135, 1.04 |
No. of reflections | 3762 |
No. of parameters | 230 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.33 |
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, 2002), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
N1—C5 | 1.330 (2) | C3—N3 | 1.394 (2) |
N1—N2 | 1.369 (2) | N3—C37 | 1.283 (2) |
N2—C3 | 1.367 (2) | C37—C31 | 1.455 (2) |
C3—C4 | 1.375 (2) | C4—C5 | 1.404 (2) |
C5—N1—N2 | 105.23 (14) | C3—C4—C5 | 105.61 (16) |
C3—N2—N1 | 111.23 (13) | N1—C5—C4 | 111.28 (15) |
N2—C3—C4 | 106.64 (15) | ||
C3—N2—C21—C22 | −25.9 (3) | C3—N3—C37—C31 | 173.83 (15) |
N1—N2—C21—C22 | 151.18 (16) | N3—C37—C31—C32 | −11.9 (3) |
C3—N2—C21—C26 | 155.84 (17) | N3—C37—C31—C36 | 170.00 (16) |
N1—N2—C21—C26 | −27.0 (2) | C33—C34—O34—C341 | 5.1 (2) |
N2—C3—N3—C37 | 146.59 (16) | C35—C34—O34—C341 | −175.37 (15) |
C4—C3—N3—C37 | −40.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O34i | 0.95 | 2.59 | 3.487 (2) | 157 |
C25—H25···Cg1ii | 0.95 | 2.73 | 3.472 (2) | 135 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y+1/2, −z+1/2. |
The title compound, (I), was prepared as an intermediate in the preparation of new pyrazole fused derivatives (see Scheme below).
There are no unusual bonds or angles (Table 1) in the pyrazole ring, which is planar to within experimental error.
The mean plane of the phenyl ring attached to N2 is tilted at 26.70 (9)° to the mean plane of the pyrazole ring. The torsion angles involving the methoxy carbon, C341, show that the methoxy group is almost but not quite coplanar with the phenyl ring to which it is attached [C33–C34–O34–C341 = 5.1 (2)°], there is a tendency for methoxy groups to be coplanar with the phenyl ring in anisoles [see Domiano et al. (1979)]
The supramolecular structure is determined by two very weak interactions involving phenyl H atoms (Table 2). The C4—H4···O34 bond links the molecules at (x, y, z) and (1 − x, −y, −z) into a a head-to-tail centrosymmetric R22(20) dimer (Bernstein et al., 1995), formed about the centre of symmetry at (1/2, 0,0) (Fig. 2). These dimers are then linked by a C—H···π interaction into a ribbon which runs parallel to the b axis, this is formed by the interaction C25—H25···centroid of the phenyl ring attached to N2 (Fig. 3).
Examination of the structure with PLATON (Spek, 2002) showed that there were no solvent-accessible voids in the crystal lattice.