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The structure of C
19H
12N
4O
4 contains one strong intramolecular O—H.
O bond giving an
S(6) motif. The molecules are linked together by weak C—H
O and C—H
N hydrogen bonds, forming a complex three-dimensional network of chain and ring motifs.
Supporting information
CCDC reference: 159762
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.124
- Data-to-parameter ratio = 8.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_707 Alert C D...A Calc 3.306(4), Rep 3.301(4), Dev. 1.25 Sigma
C5 -O62 1.555 1.455
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.44
From the CIF: _reflns_number_total 2022
Count of symmetry unique reflns 2042
Completeness (_total/calc) 99.02%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
An equimolar mixture of 3-formylchromone and 5-amino-3-(4-nitrophenyl)pyrazole
in ethanol was heated to reflux for 10 min. The title compound precipitated,
was separated by filtration and recrystallized from DMF, affording crystals
suitable for X-ray diffraction. M.p. 553–555 K, yield: 90%.
H atoms were treated as riding with distances C—H = 0.95 Å and O—-H = 0.90 Å.
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, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
6-(2-Hydroxybenzoyl)-2-(4-nitrophenyl)pyrazolo[1,5-
a]pyrimidine
top
Crystal data top
C19H12N4O4 | Dx = 1.566 Mg m−3 |
Mr = 360.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 7067 reflections |
a = 5.5421 (2) Å | θ = 1.0–27.5° |
b = 11.5858 (5) Å | µ = 0.11 mm−1 |
c = 23.8057 (13) Å | T = 150 K |
V = 1528.56 (12) Å3 | Needle, yellow |
Z = 4 | 0.20 × 0.08 × 0.07 mm |
F(000) = 744 | |
Data collection top
KappaCCD diffractometer | 2022 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ and ω scans with κ offsets | θmax = 27.4°, θmin = 1.7° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −7→7 |
Tmin = 0.978, Tmax = 0.992 | k = −15→15 |
7572 measured reflections | l = −30→30 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.3279P] where P = (Fo2 + 2Fc2)/3 |
2022 reflections | (Δ/σ)max = 0.005 |
244 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C19H12N4O4 | V = 1528.56 (12) Å3 |
Mr = 360.33 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.5421 (2) Å | µ = 0.11 mm−1 |
b = 11.5858 (5) Å | T = 150 K |
c = 23.8057 (13) Å | 0.20 × 0.08 × 0.07 mm |
Data collection top
KappaCCD diffractometer | 2022 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 1364 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.992 | Rint = 0.037 |
7572 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.25 e Å−3 |
2022 reflections | Δρmin = −0.27 e Å−3 |
244 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4216 (5) | 0.2523 (2) | 0.38267 (13) | 0.0246 (7) | |
C2 | 0.2294 (6) | 0.2706 (3) | 0.41569 (16) | 0.0231 (8) | |
C21 | 0.2235 (7) | 0.3756 (3) | 0.45031 (16) | 0.0236 (8) | |
C22 | 0.4135 (7) | 0.4528 (3) | 0.44951 (17) | 0.0292 (9) | |
C23 | 0.4127 (7) | 0.5509 (3) | 0.48185 (18) | 0.0313 (9) | |
C24 | 0.2193 (7) | 0.5701 (3) | 0.51646 (16) | 0.0270 (9) | |
N24 | 0.2188 (7) | 0.6734 (3) | 0.55150 (15) | 0.0354 (9) | |
O21 | 0.3823 (6) | 0.7435 (2) | 0.54588 (14) | 0.0465 (8) | |
O22 | 0.0492 (6) | 0.6874 (2) | 0.58380 (14) | 0.0490 (9) | |
C25 | 0.0268 (7) | 0.4960 (3) | 0.51892 (17) | 0.0299 (9) | |
C26 | 0.0278 (6) | 0.3979 (3) | 0.48571 (16) | 0.0261 (8) | |
C3 | 0.0589 (6) | 0.1814 (3) | 0.41285 (16) | 0.0242 (8) | |
C3A | 0.1556 (6) | 0.1025 (3) | 0.37594 (16) | 0.0235 (8) | |
N4 | 0.0807 (6) | −0.0027 (2) | 0.35731 (14) | 0.0267 (8) | |
C5 | 0.2270 (7) | −0.0559 (3) | 0.32334 (16) | 0.0270 (9) | |
C6 | 0.4488 (7) | −0.0104 (3) | 0.30287 (17) | 0.0260 (9) | |
C67 | 0.6017 (6) | −0.0860 (3) | 0.26614 (17) | 0.0274 (9) | |
O67 | 0.5901 (5) | −0.1918 (2) | 0.27446 (13) | 0.0364 (7) | |
C61 | 0.7653 (6) | −0.0379 (3) | 0.22383 (16) | 0.0244 (9) | |
C62 | 0.9607 (7) | −0.1058 (3) | 0.20466 (16) | 0.0261 (9) | |
O62 | 0.9951 (5) | −0.21614 (19) | 0.22193 (11) | 0.0292 (6) | |
C63 | 1.1303 (7) | −0.0592 (3) | 0.16808 (16) | 0.0295 (9) | |
C64 | 1.0969 (7) | 0.0512 (3) | 0.14697 (17) | 0.0312 (9) | |
C65 | 0.8972 (8) | 0.1152 (3) | 0.16177 (17) | 0.0324 (10) | |
C66 | 0.7353 (7) | 0.0720 (3) | 0.20037 (16) | 0.0284 (9) | |
C7 | 0.5201 (7) | 0.0945 (3) | 0.32124 (15) | 0.0241 (8) | |
N7A | 0.3740 (5) | 0.1493 (2) | 0.35832 (13) | 0.0227 (7) | |
H22 | 0.5483 | 0.4376 | 0.4260 | 0.035* | |
H23 | 0.5428 | 0.6042 | 0.4803 | 0.038* | |
H25 | −0.1055 | 0.5118 | 0.5431 | 0.036* | |
H26 | −0.1044 | 0.3457 | 0.4870 | 0.031* | |
H3 | −0.0907 | 0.1765 | 0.4322 | 0.029* | |
H5 | 0.1824 | −0.1310 | 0.3112 | 0.032* | |
H62 | 0.8597 | −0.2375 | 0.2399 | 0.035* | |
H63 | 1.2683 | −0.1028 | 0.1576 | 0.035* | |
H64 | 1.2130 | 0.0831 | 0.1220 | 0.037* | |
H65 | 0.8711 | 0.1889 | 0.1454 | 0.039* | |
H66 | 0.6009 | 0.1177 | 0.2113 | 0.034* | |
H7 | 0.6666 | 0.1285 | 0.3087 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0256 (16) | 0.0248 (16) | 0.0234 (17) | 0.0000 (13) | 0.0001 (15) | −0.0026 (15) |
C2 | 0.0191 (18) | 0.030 (2) | 0.0200 (19) | −0.0002 (15) | −0.0006 (17) | 0.0047 (17) |
C21 | 0.0227 (19) | 0.024 (2) | 0.024 (2) | 0.0025 (15) | 0.0004 (17) | 0.0001 (16) |
C22 | 0.026 (2) | 0.031 (2) | 0.031 (2) | −0.0024 (17) | 0.0068 (18) | −0.0041 (19) |
C23 | 0.028 (2) | 0.031 (2) | 0.035 (2) | −0.0028 (17) | 0.000 (2) | 0.000 (2) |
C24 | 0.032 (2) | 0.026 (2) | 0.023 (2) | 0.0011 (17) | −0.0002 (18) | 0.0008 (18) |
N24 | 0.044 (2) | 0.037 (2) | 0.0248 (19) | 0.0028 (18) | 0.0022 (19) | −0.0056 (17) |
O21 | 0.0533 (19) | 0.0376 (17) | 0.049 (2) | −0.0140 (16) | 0.0074 (17) | −0.0150 (16) |
O22 | 0.064 (2) | 0.0443 (18) | 0.0391 (19) | 0.0021 (16) | 0.0189 (19) | −0.0096 (15) |
C25 | 0.030 (2) | 0.034 (2) | 0.025 (2) | 0.0036 (18) | 0.0060 (18) | 0.0030 (19) |
C26 | 0.0226 (18) | 0.029 (2) | 0.026 (2) | −0.0028 (17) | 0.0020 (17) | 0.0010 (18) |
C3 | 0.0219 (18) | 0.031 (2) | 0.020 (2) | −0.0003 (16) | 0.0001 (17) | 0.0012 (17) |
C3A | 0.0190 (18) | 0.028 (2) | 0.023 (2) | 0.0011 (15) | −0.0028 (16) | 0.0037 (19) |
N4 | 0.0250 (16) | 0.0268 (17) | 0.0282 (19) | −0.0032 (14) | −0.0016 (15) | −0.0020 (15) |
C5 | 0.028 (2) | 0.027 (2) | 0.026 (2) | −0.0041 (17) | −0.0028 (18) | −0.0009 (17) |
C6 | 0.0273 (19) | 0.024 (2) | 0.026 (2) | −0.0001 (16) | 0.0025 (18) | 0.0008 (17) |
C67 | 0.025 (2) | 0.029 (2) | 0.028 (2) | 0.0009 (17) | −0.0043 (17) | −0.0038 (17) |
O67 | 0.0444 (17) | 0.0226 (14) | 0.0423 (19) | −0.0017 (13) | 0.0068 (15) | −0.0004 (13) |
C61 | 0.0216 (18) | 0.028 (2) | 0.023 (2) | 0.0006 (16) | 0.0005 (18) | −0.0033 (17) |
C62 | 0.0297 (19) | 0.023 (2) | 0.025 (2) | 0.0008 (16) | −0.0075 (17) | −0.0054 (17) |
O62 | 0.0362 (15) | 0.0234 (13) | 0.0281 (15) | 0.0051 (11) | 0.0010 (14) | −0.0003 (12) |
C63 | 0.028 (2) | 0.035 (2) | 0.026 (2) | 0.0050 (18) | 0.0034 (18) | −0.0044 (19) |
C64 | 0.037 (2) | 0.031 (2) | 0.026 (2) | −0.0025 (18) | 0.0044 (19) | −0.0040 (19) |
C65 | 0.046 (2) | 0.025 (2) | 0.027 (2) | 0.0009 (19) | 0.003 (2) | 0.0006 (18) |
C66 | 0.034 (2) | 0.027 (2) | 0.025 (2) | 0.0059 (17) | −0.0038 (19) | −0.0054 (17) |
C7 | 0.0209 (18) | 0.028 (2) | 0.023 (2) | 0.0006 (16) | 0.0021 (16) | 0.0020 (16) |
N7A | 0.0208 (15) | 0.0235 (16) | 0.0237 (17) | −0.0009 (13) | 0.0001 (14) | 0.0008 (14) |
Geometric parameters (Å, º) top
N1—C2 | 1.341 (5) | N4—C5 | 1.300 (5) |
N1—N7A | 1.353 (4) | C5—C6 | 1.424 (5) |
C2—C3 | 1.402 (5) | C5—H5 | 0.9500 |
C2—C21 | 1.470 (5) | C6—C7 | 1.351 (5) |
C21—C22 | 1.382 (5) | C6—C67 | 1.500 (5) |
C21—C26 | 1.397 (5) | C67—O67 | 1.244 (4) |
C22—C23 | 1.373 (5) | C67—C61 | 1.465 (5) |
C22—H22 | 0.9500 | C61—C66 | 1.401 (5) |
C23—C24 | 1.370 (5) | C61—C62 | 1.415 (5) |
C23—H23 | 0.9500 | C62—O62 | 1.356 (4) |
C24—C25 | 1.371 (5) | C62—C63 | 1.390 (5) |
C24—N24 | 1.460 (5) | O62—H62 | 0.8980 |
N24—O21 | 1.224 (4) | C63—C64 | 1.387 (6) |
N24—O22 | 1.225 (4) | C63—H63 | 0.9500 |
C25—C26 | 1.385 (5) | C64—C65 | 1.377 (5) |
C25—H25 | 0.9500 | C64—H64 | 0.9500 |
C26—H26 | 0.9500 | C65—C66 | 1.378 (5) |
C3—C3A | 1.377 (5) | C65—H65 | 0.9500 |
C3—H3 | 0.9500 | C66—H66 | 0.9500 |
C3A—N4 | 1.362 (5) | C7—N7A | 1.356 (5) |
C3A—N7A | 1.391 (5) | C7—H7 | 0.9500 |
| | | |
C2—N1—N7A | 103.6 (3) | N4—C5—H5 | 117.4 |
N1—C2—C3 | 113.0 (3) | C6—C5—H5 | 117.4 |
N1—C2—C21 | 118.5 (3) | C7—C6—C5 | 118.4 (4) |
C3—C2—C21 | 128.5 (3) | C7—C6—C67 | 123.3 (3) |
C22—C21—C26 | 118.7 (3) | C5—C6—C67 | 118.1 (3) |
C22—C21—C2 | 120.7 (3) | O67—C67—C61 | 121.1 (3) |
C26—C21—C2 | 120.6 (3) | O67—C67—C6 | 117.0 (3) |
C23—C22—C21 | 121.7 (4) | C61—C67—C6 | 121.9 (3) |
C23—C22—H22 | 119.1 | C66—C61—C62 | 117.9 (4) |
C21—C22—H22 | 119.1 | C66—C61—C67 | 123.1 (3) |
C24—C23—C22 | 118.3 (4) | C62—C61—C67 | 119.0 (3) |
C24—C23—H23 | 120.9 | O62—C62—C63 | 117.5 (3) |
C22—C23—H23 | 120.9 | O62—C62—C61 | 122.3 (3) |
C23—C24—C25 | 122.2 (4) | C63—C62—C61 | 120.2 (3) |
C23—C24—N24 | 118.6 (4) | C62—O62—H62 | 106.6 |
C25—C24—N24 | 119.2 (4) | C64—C63—C62 | 119.7 (4) |
O21—N24—O22 | 123.3 (3) | C64—C63—H63 | 120.2 |
O21—N24—C24 | 118.7 (3) | C62—C63—H63 | 120.2 |
O22—N24—C24 | 118.0 (3) | C65—C64—C63 | 120.7 (4) |
C24—C25—C26 | 119.1 (4) | C65—C64—H64 | 119.7 |
C24—C25—H25 | 120.4 | C63—C64—H64 | 119.7 |
C26—C25—H25 | 120.4 | C66—C65—C64 | 119.9 (4) |
C25—C26—C21 | 119.9 (3) | C66—C65—H65 | 120.0 |
C25—C26—H26 | 120.0 | C64—C65—H65 | 120.0 |
C21—C26—H26 | 120.0 | C65—C66—C61 | 121.2 (4) |
C3A—C3—C2 | 105.0 (3) | C65—C66—H66 | 119.4 |
C3A—C3—H3 | 127.5 | C61—C66—H66 | 119.4 |
C2—C3—H3 | 127.5 | C6—C7—N7A | 117.2 (3) |
N4—C3A—C3 | 133.1 (3) | C6—C7—H7 | 121.4 |
N4—C3A—N7A | 121.1 (3) | N7A—C7—H7 | 121.4 |
C3—C3A—N7A | 105.8 (3) | N1—N7A—C7 | 125.1 (3) |
C5—N4—C3A | 115.9 (3) | N1—N7A—C3A | 112.6 (3) |
N4—C5—C6 | 125.2 (4) | C7—N7A—C3A | 122.2 (3) |
| | | |
N7A—N1—C2—C3 | −0.2 (4) | C7—C6—C67—O67 | 143.9 (4) |
N7A—N1—C2—C21 | 178.4 (3) | C5—C6—C67—O67 | −30.4 (5) |
N1—C2—C21—C22 | −1.0 (5) | C7—C6—C67—C61 | −33.7 (6) |
C3—C2—C21—C22 | 177.3 (4) | C5—C6—C67—C61 | 152.0 (4) |
N1—C2—C21—C26 | −179.5 (4) | O67—C67—C61—C66 | 159.5 (4) |
C3—C2—C21—C26 | −1.1 (6) | C6—C67—C61—C66 | −23.0 (6) |
C26—C21—C22—C23 | −1.0 (6) | O67—C67—C61—C62 | −19.3 (6) |
C2—C21—C22—C23 | −179.5 (4) | C6—C67—C61—C62 | 158.2 (3) |
C21—C22—C23—C24 | 1.5 (6) | C66—C61—C62—O62 | −175.4 (3) |
C22—C23—C24—C25 | −1.2 (6) | C67—C61—C62—O62 | 3.5 (5) |
C22—C23—C24—N24 | 179.2 (4) | C66—C61—C62—C63 | 6.5 (5) |
C23—C24—N24—O21 | 5.2 (5) | C67—C61—C62—C63 | −174.7 (3) |
C25—C24—N24—O21 | −174.4 (4) | O62—C62—C63—C64 | 176.8 (3) |
C23—C24—N24—O22 | −177.3 (4) | C61—C62—C63—C64 | −5.0 (6) |
C25—C24—N24—O22 | 3.1 (5) | C62—C63—C64—C65 | −0.1 (6) |
C23—C24—C25—C26 | 0.5 (6) | C63—C64—C65—C66 | 3.7 (6) |
N24—C24—C25—C26 | −179.9 (3) | C64—C65—C66—C61 | −2.1 (6) |
C24—C25—C26—C21 | 0.0 (5) | C62—C61—C66—C65 | −3.0 (5) |
C22—C21—C26—C25 | 0.2 (6) | C67—C61—C66—C65 | 178.2 (4) |
C2—C21—C26—C25 | 178.7 (3) | C5—C6—C7—N7A | 0.1 (5) |
N1—C2—C3—C3A | 0.7 (4) | C67—C6—C7—N7A | −174.1 (3) |
C21—C2—C3—C3A | −177.7 (4) | C2—N1—N7A—C7 | −179.6 (3) |
C2—C3—C3A—N4 | 177.6 (4) | C2—N1—N7A—C3A | −0.4 (4) |
C2—C3—C3A—N7A | −0.9 (4) | C6—C7—N7A—N1 | 177.2 (3) |
C3—C3A—N4—C5 | −177.3 (4) | C6—C7—N7A—C3A | −1.9 (5) |
N7A—C3A—N4—C5 | 1.1 (5) | N4—C3A—N7A—N1 | −177.9 (3) |
C3A—N4—C5—C6 | −3.0 (5) | C3—C3A—N7A—N1 | 0.9 (4) |
N4—C5—C6—C7 | 2.5 (6) | N4—C3A—N7A—C7 | 1.3 (5) |
N4—C5—C6—C67 | 177.0 (4) | C3—C3A—N7A—C7 | −179.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O62i | 0.95 | 2.56 | 3.301 (4) | 135 |
C63—H63···N1ii | 0.95 | 2.58 | 3.519 (5) | 168 |
C66—H66···O67iii | 0.95 | 2.47 | 3.332 (4) | 150 |
O62—H62···O67 | 0.90 | 1.78 | 2.583 (4) | 147 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | C19H12N4O4 |
Mr | 360.33 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 5.5421 (2), 11.5858 (5), 23.8057 (13) |
V (Å3) | 1528.56 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.20 × 0.08 × 0.07 |
|
Data collection |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.978, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7572, 2022, 1364 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.648 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.124, 1.07 |
No. of reflections | 2022 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.27 |
Selected geometric parameters (Å, º) topN1—C2 | 1.341 (5) | C3A—N4 | 1.362 (5) |
N1—N7A | 1.353 (4) | C3A—N7A | 1.391 (5) |
C24—N24 | 1.460 (5) | C7—N7A | 1.356 (5) |
| | | |
C2—N1—N7A | 103.6 (3) | C5—N4—C3A | 115.9 (3) |
O21—N24—O22 | 123.3 (3) | N1—N7A—C7 | 125.1 (3) |
O21—N24—C24 | 118.7 (3) | N1—N7A—C3A | 112.6 (3) |
O22—N24—C24 | 118.0 (3) | C7—N7A—C3A | 122.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O62i | 0.95 | 2.56 | 3.301 (4) | 135 |
C63—H63···N1ii | 0.95 | 2.58 | 3.519 (5) | 168 |
C66—H66···O67iii | 0.95 | 2.47 | 3.332 (4) | 150 |
O62—H62···O67 | 0.90 | 1.78 | 2.583 (4) | 147 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
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Since becoming readily available, 3-formylchromone has been used to prepare a variety of heterocyclic systems (Jones & Albrecht, 1976; Haas et al., 1981; Pene & Hubert-Habart, 1980; Sigg et al., 1982). In our investigation of pyrazolo[1,5-a]pyrimidines, we have established that the cyclocondensation reaction of 5-amino-1H-pyrazoles with α,β-unsaturated aromatic ketones is a versatile and efficient method for the preparation of these compounds (Orlov et al., 1988; Quiroga et al., 1994, 1999), but the reaction with 3-formylchromone was not previously investigated. We have recently applied above methodology to prepare several pyrazolo[1,5-a]pyrimidines starting from 3-formylchromone.
Geometric parameters for the title compound, (I), are given in Table 1 and hydrogen-bond parameters are given in Table 2. The three-dimensional hydrogen-bonding network produced by the weak intermolecular C—H···O and C—H···N hydrogen bonds is very complex, the simpler motifs being three infinite chains based on the following motifs; a C(7) motif (Bernstein et al., 1995) involving C5—H5···O62i, a C(5) motif in which C66—H66···O67iii and a C22(12) motif in which C66—H66···O67iii and C63—H63···N1ii [symmetry codes: (i) x - 1, y, z; (iii) 1 - x, y + 1/2, -z + 1/2]. The chains produced by repeat of these motifs creates ring motifs which in turn produce a three-dimensional network. A view of the molecule is shown in Fig. 1.
Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.