Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018208/om6158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018208/om6158Isup2.hkl |
CCDC reference: 222872
A mixture of 5-amino-3-methyl-1-phenylpyrazole (10 mmol) and 2-pyridinecarbaldehyde (20 mmol) was placed into Pyrex-glass open vessels and irradiated in a domestic microwave oven for 1.5 min (at 600 W). The solid was filtered, washed with ethanol, dried and recrystalized from ethanol. Yield 68%, m.p. 517 K. Analysis calculated for C27H21N5: C 78.05, H 5.09, N 16.86%; found: C 78.08, H 5.03, N 16.81%.
Molecule (I) crystallized in the triclinic system; space group P1 was assumed and confirmed by the analysis. H atoms were treated as riding atoms, with C—H = 0.95 Å (aromatic) and 0.98 Å (methyl).
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, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C26H20N6 | F(000) = 436 |
Mr = 416.48 | Dx = 1.353 Mg m−3 |
Triclinic, P1 | Melting point: 517 K |
a = 8.4576 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6599 (3) Å | Cell parameters from 4637 reflections |
c = 12.3642 (4) Å | θ = 3.1–27.5° |
α = 106.9170 (14)° | µ = 0.08 mm−1 |
β = 98.6240 (16)° | T = 120 K |
γ = 100.803 (2)° | Block, brown |
V = 1022.48 (5) Å3 | 0.28 × 0.22 × 0.18 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 4637 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3732 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ϕ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.977, Tmax = 0.985 | k = −13→13 |
19117 measured reflections | l = −16→15 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1734P] where P = (Fo2 + 2Fc2)/3 |
4637 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C26H20N6 | γ = 100.803 (2)° |
Mr = 416.48 | V = 1022.48 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4576 (2) Å | Mo Kα radiation |
b = 10.6599 (3) Å | µ = 0.08 mm−1 |
c = 12.3642 (4) Å | T = 120 K |
α = 106.9170 (14)° | 0.28 × 0.22 × 0.18 mm |
β = 98.6240 (16)° |
Nonius KappaCCD diffractometer | 4637 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 3732 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.985 | Rint = 0.050 |
19117 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.25 e Å−3 |
4637 reflections | Δρmin = −0.25 e Å−3 |
291 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 | 0.31352 (11) | 0.06622 (9) | −0.02226 (8) | 0.0183 (2) | |
N2 | 0.46861 (12) | 0.25463 (10) | −0.06259 (8) | 0.0197 (2) | |
N3 | 0.60148 (12) | 0.36471 (10) | −0.00499 (8) | 0.0214 (2) | |
N7 | 0.22367 (12) | −0.10898 (10) | 0.17481 (8) | 0.0219 (2) | |
N8 | 0.19836 (12) | −0.09346 (10) | 0.06625 (8) | 0.0194 (2) | |
N52 | 0.60600 (13) | 0.38270 (11) | 0.38405 (9) | 0.0257 (2) | |
C1A | 0.43165 (14) | 0.18011 (11) | 0.00781 (10) | 0.0178 (2) | |
C4 | 0.64613 (14) | 0.36174 (11) | 0.10053 (10) | 0.0195 (2) | |
C4A | 0.54369 (13) | 0.24750 (11) | 0.11638 (10) | 0.0179 (2) | |
C5 | 0.53309 (13) | 0.19511 (11) | 0.20688 (10) | 0.0177 (2) | |
C5A | 0.41189 (14) | 0.07542 (11) | 0.17944 (9) | 0.0181 (2) | |
C6 | 0.34921 (14) | −0.01033 (12) | 0.24163 (10) | 0.0207 (3) | |
C8A | 0.30884 (13) | 0.01859 (11) | 0.06626 (10) | 0.0174 (2) | |
C21 | 0.39228 (14) | 0.23594 (11) | −0.17791 (10) | 0.0196 (2) | |
C22 | 0.22943 (15) | 0.16217 (12) | −0.22427 (10) | 0.0229 (3) | |
C23 | 0.15769 (15) | 0.14562 (13) | −0.33791 (11) | 0.0257 (3) | |
C24 | 0.24560 (16) | 0.20351 (13) | −0.40458 (11) | 0.0267 (3) | |
C25 | 0.40694 (16) | 0.27891 (13) | −0.35671 (11) | 0.0266 (3) | |
C26 | 0.48110 (15) | 0.29504 (12) | −0.24422 (10) | 0.0240 (3) | |
C41 | 0.78873 (15) | 0.46651 (12) | 0.18448 (10) | 0.0233 (3) | |
C51 | 0.63797 (14) | 0.26626 (12) | 0.32535 (10) | 0.0193 (2) | |
C53 | 0.69853 (16) | 0.44902 (13) | 0.49086 (11) | 0.0296 (3) | |
C54 | 0.82234 (16) | 0.40458 (15) | 0.54260 (12) | 0.0342 (3) | |
C55 | 0.85259 (17) | 0.28416 (17) | 0.48169 (12) | 0.0390 (4) | |
C56 | 0.75932 (16) | 0.21315 (14) | 0.37111 (11) | 0.0307 (3) | |
C61 | 0.40634 (16) | 0.00020 (13) | 0.36462 (10) | 0.0264 (3) | |
C81 | 0.06302 (14) | −0.18390 (11) | −0.02100 (10) | 0.0186 (2) | |
C82 | 0.01656 (15) | −0.16302 (12) | −0.12590 (10) | 0.0223 (3) | |
C83 | −0.12059 (15) | −0.25137 (12) | −0.20700 (11) | 0.0242 (3) | |
C84 | −0.21210 (15) | −0.35990 (12) | −0.18481 (11) | 0.0245 (3) | |
C85 | −0.16322 (15) | −0.38136 (13) | −0.08105 (11) | 0.0258 (3) | |
C86 | −0.02569 (15) | −0.29492 (12) | 0.00072 (10) | 0.0235 (3) | |
H22 | 0.1679 | 0.1235 | −0.1786 | 0.028* | |
H23 | 0.0472 | 0.0941 | −0.3702 | 0.031* | |
H24 | 0.1960 | 0.1917 | −0.4822 | 0.032* | |
H25 | 0.4671 | 0.3199 | −0.4017 | 0.032* | |
H26 | 0.5919 | 0.3461 | −0.2124 | 0.029* | |
H41A | 0.8357 | 0.5298 | 0.1473 | 0.035* | |
H41B | 0.8729 | 0.4228 | 0.2093 | 0.035* | |
H41C | 0.7513 | 0.5158 | 0.2520 | 0.035* | |
H53 | 0.6773 | 0.5317 | 0.5334 | 0.036* | |
H54 | 0.8854 | 0.4556 | 0.6184 | 0.041* | |
H55 | 0.9366 | 0.2502 | 0.5153 | 0.047* | |
H56 | 0.7780 | 0.1299 | 0.3275 | 0.037* | |
H61A | 0.3288 | −0.0659 | 0.3842 | 0.040* | |
H61B | 0.4119 | 0.0915 | 0.4152 | 0.040* | |
H61C | 0.5160 | −0.0180 | 0.3753 | 0.040* | |
H82 | 0.0781 | −0.0889 | −0.1420 | 0.027* | |
H83 | −0.1522 | −0.2373 | −0.2787 | 0.029* | |
H84 | −0.3071 | −0.4187 | −0.2401 | 0.029* | |
H85 | −0.2245 | −0.4561 | −0.0656 | 0.031* | |
H86 | 0.0079 | −0.3113 | 0.0712 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0201 (5) | 0.0176 (5) | 0.0168 (5) | 0.0040 (4) | 0.0040 (4) | 0.0057 (4) |
N2 | 0.0206 (5) | 0.0181 (5) | 0.0173 (5) | −0.0002 (4) | 0.0010 (4) | 0.0056 (4) |
N3 | 0.0212 (5) | 0.0182 (5) | 0.0210 (5) | 0.0004 (4) | 0.0021 (4) | 0.0047 (4) |
N7 | 0.0267 (5) | 0.0229 (5) | 0.0165 (5) | 0.0049 (4) | 0.0043 (4) | 0.0077 (4) |
N8 | 0.0217 (5) | 0.0190 (5) | 0.0159 (5) | 0.0017 (4) | 0.0020 (4) | 0.0067 (4) |
N52 | 0.0292 (6) | 0.0236 (5) | 0.0196 (5) | 0.0067 (4) | 0.0001 (4) | 0.0026 (4) |
C1A | 0.0179 (5) | 0.0172 (5) | 0.0182 (6) | 0.0047 (4) | 0.0038 (4) | 0.0055 (4) |
C4 | 0.0192 (6) | 0.0178 (6) | 0.0203 (6) | 0.0043 (5) | 0.0038 (4) | 0.0048 (4) |
C4A | 0.0176 (5) | 0.0172 (5) | 0.0168 (6) | 0.0041 (4) | 0.0025 (4) | 0.0033 (4) |
C5 | 0.0173 (5) | 0.0177 (5) | 0.0178 (6) | 0.0067 (4) | 0.0034 (4) | 0.0043 (4) |
C5A | 0.0197 (5) | 0.0181 (6) | 0.0158 (5) | 0.0059 (4) | 0.0027 (4) | 0.0044 (4) |
C6 | 0.0232 (6) | 0.0198 (6) | 0.0184 (6) | 0.0058 (5) | 0.0039 (5) | 0.0052 (5) |
C8A | 0.0178 (5) | 0.0167 (5) | 0.0174 (5) | 0.0048 (4) | 0.0040 (4) | 0.0045 (4) |
C21 | 0.0246 (6) | 0.0183 (6) | 0.0157 (6) | 0.0070 (5) | 0.0019 (4) | 0.0054 (4) |
C22 | 0.0239 (6) | 0.0240 (6) | 0.0222 (6) | 0.0057 (5) | 0.0042 (5) | 0.0099 (5) |
C23 | 0.0228 (6) | 0.0275 (6) | 0.0243 (6) | 0.0061 (5) | −0.0006 (5) | 0.0077 (5) |
C24 | 0.0314 (7) | 0.0317 (7) | 0.0187 (6) | 0.0128 (5) | 0.0033 (5) | 0.0087 (5) |
C25 | 0.0324 (7) | 0.0297 (7) | 0.0227 (6) | 0.0100 (5) | 0.0090 (5) | 0.0128 (5) |
C26 | 0.0258 (6) | 0.0237 (6) | 0.0228 (6) | 0.0048 (5) | 0.0048 (5) | 0.0092 (5) |
C41 | 0.0226 (6) | 0.0199 (6) | 0.0228 (6) | 0.0008 (5) | 0.0024 (5) | 0.0041 (5) |
C51 | 0.0182 (5) | 0.0207 (6) | 0.0172 (6) | 0.0025 (4) | 0.0020 (4) | 0.0059 (4) |
C53 | 0.0333 (7) | 0.0270 (7) | 0.0208 (6) | 0.0039 (5) | 0.0015 (5) | 0.0007 (5) |
C54 | 0.0256 (7) | 0.0449 (8) | 0.0215 (7) | 0.0023 (6) | −0.0022 (5) | 0.0027 (6) |
C55 | 0.0286 (7) | 0.0576 (10) | 0.0291 (7) | 0.0187 (7) | −0.0036 (6) | 0.0115 (7) |
C56 | 0.0293 (7) | 0.0355 (7) | 0.0261 (7) | 0.0149 (6) | 0.0015 (5) | 0.0058 (6) |
C61 | 0.0325 (7) | 0.0274 (7) | 0.0177 (6) | 0.0037 (5) | 0.0034 (5) | 0.0081 (5) |
C81 | 0.0178 (5) | 0.0181 (5) | 0.0172 (6) | 0.0040 (4) | 0.0034 (4) | 0.0024 (4) |
C82 | 0.0243 (6) | 0.0199 (6) | 0.0210 (6) | 0.0027 (5) | 0.0033 (5) | 0.0065 (5) |
C83 | 0.0253 (6) | 0.0246 (6) | 0.0205 (6) | 0.0057 (5) | 0.0012 (5) | 0.0064 (5) |
C84 | 0.0201 (6) | 0.0235 (6) | 0.0238 (6) | 0.0023 (5) | 0.0028 (5) | 0.0015 (5) |
C85 | 0.0250 (6) | 0.0222 (6) | 0.0263 (6) | −0.0006 (5) | 0.0068 (5) | 0.0056 (5) |
C86 | 0.0255 (6) | 0.0236 (6) | 0.0202 (6) | 0.0026 (5) | 0.0052 (5) | 0.0076 (5) |
N1—C1A | 1.3347 (15) | C25—C26 | 1.3842 (17) |
N1—C8A | 1.3364 (15) | C25—H25 | 0.95 |
N2—C1A | 1.3702 (15) | C26—H26 | 0.95 |
N2—N3 | 1.3879 (13) | C41—H41A | 0.98 |
N2—C21 | 1.4142 (14) | C41—H41B | 0.98 |
N3—C4 | 1.3139 (15) | C41—H41C | 0.98 |
N7—C6 | 1.3147 (15) | C51—C56 | 1.3871 (17) |
N7—N8 | 1.3896 (13) | C53—C54 | 1.3753 (19) |
N8—C8A | 1.3717 (15) | C53—H53 | 0.95 |
N8—C81 | 1.4192 (14) | C54—C55 | 1.378 (2) |
N52—C53 | 1.3400 (16) | C54—H54 | 0.95 |
N52—C51 | 1.3420 (15) | C55—C56 | 1.3838 (19) |
C1A—C4A | 1.4206 (15) | C55—H55 | 0.95 |
C4—C4A | 1.4375 (16) | C56—H56 | 0.95 |
C4—C41 | 1.4914 (16) | C61—H61A | 0.98 |
C4A—C5 | 1.3953 (17) | C61—H61B | 0.98 |
C5—C5A | 1.3954 (16) | C61—H61C | 0.98 |
C5—C51 | 1.4898 (15) | C81—C82 | 1.3908 (16) |
C5A—C8A | 1.4240 (15) | C81—C86 | 1.3957 (17) |
C5A—C6 | 1.4345 (17) | C82—C83 | 1.3893 (16) |
C6—C61 | 1.4894 (16) | C82—H82 | 0.95 |
C21—C22 | 1.3924 (17) | C83—C84 | 1.3877 (18) |
C21—C26 | 1.3933 (17) | C83—H83 | 0.95 |
C22—C23 | 1.3905 (17) | C84—C85 | 1.3844 (18) |
C22—H22 | 0.95 | C84—H84 | 0.95 |
C23—C24 | 1.3860 (19) | C85—C86 | 1.3883 (17) |
C23—H23 | 0.95 | C85—H85 | 0.95 |
C24—C25 | 1.3886 (18) | C86—H86 | 0.95 |
C24—H24 | 0.95 | ||
C1A—N1—C8A | 110.97 (9) | C25—C26—H26 | 120.2 |
C1A—N2—N3 | 110.74 (9) | C21—C26—H26 | 120.2 |
C1A—N2—C21 | 130.19 (10) | C4—C41—H41A | 109.5 |
N3—N2—C21 | 119.06 (9) | C4—C41—H41B | 109.5 |
C4—N3—N2 | 107.25 (9) | H41A—C41—H41B | 109.5 |
C6—N7—N8 | 107.25 (10) | C4—C41—H41C | 109.5 |
C8A—N8—N7 | 110.61 (9) | H41A—C41—H41C | 109.5 |
C8A—N8—C81 | 130.72 (10) | H41B—C41—H41C | 109.5 |
N7—N8—C81 | 118.49 (9) | N52—C51—C56 | 122.88 (11) |
C53—N52—C51 | 117.14 (10) | N52—C51—C5 | 115.80 (10) |
N1—C1A—N2 | 125.73 (10) | C56—C51—C5 | 121.31 (10) |
N1—C1A—C4A | 127.79 (10) | N52—C53—C54 | 123.90 (12) |
N2—C1A—C4A | 106.48 (10) | N52—C53—H53 | 118.0 |
N3—C4—C4A | 110.79 (10) | C54—C53—H53 | 118.0 |
N3—C4—C41 | 120.45 (11) | C53—C54—C55 | 118.28 (12) |
C4A—C4—C41 | 128.74 (11) | C53—C54—H54 | 120.9 |
C5—C4A—C1A | 119.31 (10) | C55—C54—H54 | 120.9 |
C5—C4A—C4 | 135.98 (11) | C54—C55—C56 | 119.28 (12) |
C1A—C4A—C4 | 104.71 (10) | C54—C55—H55 | 120.4 |
C5A—C5—C4A | 115.03 (10) | C56—C55—H55 | 120.4 |
C5A—C5—C51 | 122.83 (10) | C55—C56—C51 | 118.50 (12) |
C4A—C5—C51 | 122.07 (10) | C55—C56—H56 | 120.7 |
C5—C5A—C8A | 119.47 (10) | C51—C56—H56 | 120.7 |
C5—C5A—C6 | 135.71 (11) | C6—C61—H61A | 109.5 |
C8A—C5A—C6 | 104.67 (10) | C6—C61—H61B | 109.5 |
N7—C6—C5A | 110.96 (10) | H61A—C61—H61B | 109.5 |
N7—C6—C61 | 119.88 (11) | C6—C61—H61C | 109.5 |
C5A—C6—C61 | 129.15 (11) | H61A—C61—H61C | 109.5 |
N1—C8A—N8 | 126.07 (10) | H61B—C61—H61C | 109.5 |
N1—C8A—C5A | 127.41 (10) | C82—C81—C86 | 119.88 (11) |
N8—C8A—C5A | 106.49 (10) | C82—C81—N8 | 121.49 (10) |
C22—C21—C26 | 120.14 (11) | C86—C81—N8 | 118.63 (10) |
C22—C21—N2 | 120.76 (11) | C83—C82—C81 | 119.47 (11) |
C26—C21—N2 | 119.09 (10) | C83—C82—H82 | 120.3 |
C23—C22—C21 | 119.43 (11) | C81—C82—H82 | 120.3 |
C23—C22—H22 | 120.3 | C82—C83—C84 | 121.01 (12) |
C21—C22—H22 | 120.3 | C82—C83—H83 | 119.5 |
C24—C23—C22 | 120.73 (12) | C84—C83—H83 | 119.5 |
C24—C23—H23 | 119.6 | C85—C84—C83 | 119.13 (11) |
C22—C23—H23 | 119.6 | C85—C84—H84 | 120.4 |
C23—C24—C25 | 119.30 (11) | C83—C84—H84 | 120.4 |
C23—C24—H24 | 120.3 | C84—C85—C86 | 120.74 (12) |
C25—C24—H24 | 120.3 | C84—C85—H85 | 119.6 |
C26—C25—C24 | 120.78 (12) | C86—C85—H85 | 119.6 |
C26—C25—H25 | 119.6 | C85—C86—C81 | 119.74 (11) |
C24—C25—H25 | 119.6 | C85—C86—H86 | 120.1 |
C25—C26—C21 | 119.60 (11) | C81—C86—H86 | 120.1 |
C1A—N2—N3—C4 | −1.15 (12) | C5—C5A—C8A—N1 | 0.62 (17) |
C21—N2—N3—C4 | 178.00 (9) | C6—C5A—C8A—N1 | 176.81 (11) |
C6—N7—N8—C8A | −1.05 (12) | C5—C5A—C8A—N8 | −177.32 (10) |
C6—N7—N8—C81 | −176.71 (9) | C6—C5A—C8A—N8 | −1.13 (11) |
C8A—N1—C1A—N2 | −179.82 (10) | C1A—N2—C21—C22 | 22.81 (18) |
C8A—N1—C1A—C4A | 0.72 (16) | N3—N2—C21—C22 | −156.16 (10) |
N3—N2—C1A—N1 | −178.15 (10) | C1A—N2—C21—C26 | −158.64 (12) |
C21—N2—C1A—N1 | 2.82 (19) | N3—N2—C21—C26 | 22.40 (15) |
N3—N2—C1A—C4A | 1.40 (12) | C26—C21—C22—C23 | 1.40 (17) |
C21—N2—C1A—C4A | −177.63 (10) | N2—C21—C22—C23 | 179.95 (10) |
N2—N3—C4—C4A | 0.41 (12) | C21—C22—C23—C24 | −1.06 (18) |
N2—N3—C4—C41 | 179.07 (10) | C22—C23—C24—C25 | −0.10 (18) |
N1—C1A—C4A—C5 | −1.56 (17) | C23—C24—C25—C26 | 0.93 (19) |
N2—C1A—C4A—C5 | 178.90 (10) | C24—C25—C26—C21 | −0.58 (18) |
N1—C1A—C4A—C4 | 178.45 (11) | C22—C21—C26—C25 | −0.59 (17) |
N2—C1A—C4A—C4 | −1.09 (11) | N2—C21—C26—C25 | −179.16 (10) |
N3—C4—C4A—C5 | −179.56 (12) | C53—N52—C51—C56 | 0.71 (19) |
C41—C4—C4A—C5 | 1.9 (2) | C53—N52—C51—C5 | −179.94 (11) |
N3—C4—C4A—C1A | 0.43 (12) | C5A—C5—C51—N52 | −108.40 (13) |
C41—C4—C4A—C1A | −178.10 (11) | C4A—C5—C51—N52 | 68.30 (14) |
C1A—C4A—C5—C5A | 1.72 (15) | C5A—C5—C51—C56 | 70.95 (16) |
C4—C4A—C5—C5A | −178.30 (12) | C4A—C5—C51—C56 | −112.34 (14) |
C1A—C4A—C5—C51 | −175.22 (10) | C51—N52—C53—C54 | −0.1 (2) |
C4—C4A—C5—C51 | 4.8 (2) | N52—C53—C54—C55 | −0.6 (2) |
C4A—C5—C5A—C8A | −1.32 (15) | C53—C54—C55—C56 | 0.6 (2) |
C51—C5—C5A—C8A | 175.60 (10) | C54—C55—C56—C51 | 0.0 (2) |
C4A—C5—C5A—C6 | −176.03 (12) | N52—C51—C56—C55 | −0.7 (2) |
C51—C5—C5A—C6 | 0.9 (2) | C5—C51—C56—C55 | 180.00 (12) |
N8—N7—C6—C5A | 0.28 (13) | C8A—N8—C81—C82 | −3.78 (18) |
N8—N7—C6—C61 | 179.97 (10) | N7—N8—C81—C82 | 170.86 (10) |
C5—C5A—C6—N7 | 175.78 (12) | C8A—N8—C81—C86 | 177.07 (11) |
C8A—C5A—C6—N7 | 0.53 (12) | N7—N8—C81—C86 | −8.29 (15) |
C5—C5A—C6—C61 | −3.9 (2) | C86—C81—C82—C83 | 1.59 (17) |
C8A—C5A—C6—C61 | −179.12 (11) | N8—C81—C82—C83 | −177.55 (10) |
C1A—N1—C8A—N8 | 177.31 (10) | C81—C82—C83—C84 | 0.15 (18) |
C1A—N1—C8A—C5A | −0.24 (15) | C82—C83—C84—C85 | −1.31 (18) |
N7—N8—C8A—N1 | −176.60 (10) | C83—C84—C85—C86 | 0.74 (18) |
C81—N8—C8A—N1 | −1.64 (18) | C84—C85—C86—C81 | 0.98 (18) |
N7—N8—C8A—C5A | 1.37 (12) | C82—C81—C86—C85 | −2.15 (17) |
C81—N8—C8A—C5A | 176.34 (11) | N8—C81—C86—C85 | 177.02 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···N1 | 0.95 | 2.43 | 3.0029 (16) | 119 |
C82—H82···N1 | 0.95 | 2.31 | 2.9721 (16) | 126 |
C85—H85···N3i | 0.95 | 2.55 | 3.4922 (18) | 173 |
Symmetry code: (i) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C26H20N6 |
Mr | 416.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 8.4576 (2), 10.6599 (3), 12.3642 (4) |
α, β, γ (°) | 106.9170 (14), 98.6240 (16), 100.803 (2) |
V (Å3) | 1022.48 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.977, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19117, 4637, 3732 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.110, 1.03 |
No. of reflections | 4637 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.25 |
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, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
N1—C1A | 1.3347 (15) | N52—C53 | 1.3400 (16) |
N1—C8A | 1.3364 (15) | N52—C51 | 1.3420 (15) |
N2—N3 | 1.3879 (13) | C1A—C4A | 1.4206 (15) |
N3—C4 | 1.3139 (15) | C4—C4A | 1.4375 (16) |
N7—C6 | 1.3147 (15) | C4A—C5 | 1.3953 (17) |
N7—N8 | 1.3896 (13) | C5—C5A | 1.3954 (16) |
N8—C8A | 1.3717 (15) | C5A—C8A | 1.4240 (15) |
C1A—N1—C8A | 110.97 (9) | C5A—C5—C4A | 115.03 (10) |
C1A—N2—N3 | 110.74 (9) | C5A—C5—C51 | 122.83 (10) |
C1A—N2—C21 | 130.19 (10) | C4A—C5—C51 | 122.07 (10) |
N3—N2—C21 | 119.06 (9) | C5—C5A—C8A | 119.47 (10) |
C4—N3—N2 | 107.25 (9) | C5—C5A—C6 | 135.71 (11) |
C6—N7—N8 | 107.25 (10) | C8A—C5A—C6 | 104.67 (10) |
C8A—N8—N7 | 110.61 (9) | N7—C6—C5A | 110.96 (10) |
C8A—N8—C81 | 130.72 (10) | N7—C6—C61 | 119.88 (11) |
N7—N8—C81 | 118.49 (9) | C5A—C6—C61 | 129.15 (11) |
C53—N52—C51 | 117.14 (10) | N1—C8A—N8 | 126.07 (10) |
N1—C1A—N2 | 125.73 (10) | N1—C8A—C5A | 127.41 (10) |
N1—C1A—C4A | 127.79 (10) | N8—C8A—C5A | 106.49 (10) |
N2—C1A—C4A | 106.48 (10) | N52—C51—C56 | 122.88 (11) |
N3—C4—C4A | 110.79 (10) | N52—C51—C5 | 115.80 (10) |
N3—C4—C41 | 120.45 (11) | N52—C53—C54 | 123.90 (12) |
C4A—C4—C41 | 128.74 (11) | C53—C54—C55 | 118.28 (12) |
C5—C4A—C1A | 119.31 (10) | C54—C55—C56 | 119.28 (12) |
C5—C4A—C4 | 135.98 (11) | C55—C56—C51 | 118.50 (12) |
C1A—C4A—C4 | 104.71 (10) | ||
C1A—N2—C21—C22 | 22.81 (18) | C5A—C5—C51—C56 | 70.95 (16) |
N3—N2—C21—C22 | −156.16 (10) | C4A—C5—C51—C56 | −112.34 (14) |
C1A—N2—C21—C26 | −158.64 (12) | C8A—N8—C81—C82 | −3.78 (18) |
N3—N2—C21—C26 | 22.40 (15) | N7—N8—C81—C82 | 170.86 (10) |
C5A—C5—C51—N52 | −108.40 (13) | C8A—N8—C81—C86 | 177.07 (11) |
C4A—C5—C51—N52 | 68.30 (14) | N7—N8—C81—C86 | −8.29 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···N1 | 0.95 | 2.43 | 3.0029 (16) | 119 |
C82—H82···N1 | 0.95 | 2.31 | 2.9721 (16) | 126 |
C85—H85···N3i | 0.95 | 2.55 | 3.4922 (18) | 173 |
Symmetry code: (i) x−1, y−1, z. |
In our ongoing application of microwave irradiation to heterocyclic synthesis by multicomponent condensation, we have prepared compound (I) from 5-amino-3-methyl-1-phenyl-1H-pyrazole and 2-pyridinecarbadehyde.
There are no unusual bonds and angles in the structure (Fig. 1). The 12-membered fused-ring system defined by atoms N1 to C8A is essentially planar and symmetrical about the N1···C5 line, as shown by the bonds and angles in Table 1. However, the angle of tilt of the phenyl rings out of the plane of the 12-membered ring system varies as is shown by the torsion angles listed in Table 1 so that this symmetry does not extend to the whole molecule. There are two short intramolecular contacts C22—H22··· N1 and C82—H82···N1, i.e. between the two phenyl rings defined by atoms C21–C26 and C81–C86 to atom N1 (Table 2). The C8—H85···N3 weak hydrogen bond links the molecules into C(10) chains (Bernstein et al., 1995) which run parallel to [110] (Fig. 2).