Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702778X/tk2160sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702778X/tk2160Isup2.hkl |
CCDC reference: 654918
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.119
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.10 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.24 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2007); Kimura et al. (1977); Lombardino & Ottemes (1981); Manna et al. (2002); Rawal et al. (1963).
1-(p-Bromophenyl)-3-furan-2-propenyl-1-ketone (0.02 mol) and hydrazine (0.02 mol) were mixed and stirred in refluxing 99.5% acetic acid (40 ml) for 6 h. The mixture was poured into ice-water to afford colourless solids. The solids were filtered and washed with water until the pH of solution was about to 7.0.at room temperature. Single crystals of (I) suitable for the X-ray study were obtained by recrystallization from an ethanol solution of (I) held at room temperature; m. pt. 329.9 - 330.3 K.
H atoms were fixed geometrically and allowed to ride on their parent atoms with C—H distances = 0.93–0.96 Å, and with Uiso = 1.2–1.5Ueq of the parent atoms.
Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds which possess anti-viral (Rawal et al., 1963), anti-fungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Further, 1-acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit monoamine oxidases (Manna et al., 2002). As part of our on-going investgation of pyrazolines and their metal complexes, we report here the crystal structure of the title compound (I).
In the structure of (I) (Fig. 1), all bond lengths and angles fall in the normal range (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by the pyrazolinyl ring with the phenyl and furan rings are 11.3 (2) and 88.0 (2)°, respectively. There are some intermolecular C—H···O contacts (Table 1) which stabilize the structure.
For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2007); Kimura et al. (1977); Lombardino & Ottemes (1981); Manna et al. (2002); Rawal et al. (1963).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level. |
C15H13BrN2O2 | F(000) = 672 |
Mr = 333.18 | Dx = 1.587 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2387 reflections |
a = 8.1417 (17) Å | θ = 2.3–25.3° |
b = 26.757 (6) Å | µ = 2.95 mm−1 |
c = 7.0974 (15) Å | T = 298 K |
β = 115.587 (2)° | Plan, colourless |
V = 1394.5 (5) Å3 | 0.49 × 0.36 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2461 independent reflections |
Radiation source: fine-focus sealed tube | 1948 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→9 |
Tmin = 0.326, Tmax = 0.757 | k = −21→31 |
5796 measured reflections | l = −8→7 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.5202P] where P = (Fo2 + 2Fc2)/3 |
2461 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C15H13BrN2O2 | V = 1394.5 (5) Å3 |
Mr = 333.18 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1417 (17) Å | µ = 2.95 mm−1 |
b = 26.757 (6) Å | T = 298 K |
c = 7.0974 (15) Å | 0.49 × 0.36 × 0.10 mm |
β = 115.587 (2)° |
Bruker SMART CCD area-detector diffractometer | 2461 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1948 reflections with I > 2σ(I) |
Tmin = 0.326, Tmax = 0.757 | Rint = 0.044 |
5796 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.70 e Å−3 |
2461 reflections | Δρmin = −0.43 e Å−3 |
182 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0947 (5) | 0.41162 (13) | 0.4859 (5) | 0.0419 (8) | |
H1 | 0.0257 | 0.3832 | 0.4279 | 0.050* | |
C2 | 0.1101 (5) | 0.44764 (14) | 0.3554 (6) | 0.0456 (9) | |
H2 | 0.0527 | 0.4436 | 0.2112 | 0.055* | |
C3 | 0.2128 (5) | 0.48981 (13) | 0.4436 (5) | 0.0385 (8) | |
C4 | 0.2965 (5) | 0.49611 (14) | 0.6560 (6) | 0.0486 (9) | |
H4 | 0.3645 | 0.5248 | 0.7129 | 0.058* | |
C5 | 0.2800 (5) | 0.45990 (14) | 0.7856 (6) | 0.0455 (9) | |
H5 | 0.3361 | 0.4643 | 0.9297 | 0.055* | |
C6 | 0.1790 (4) | 0.41671 (13) | 0.7003 (5) | 0.0336 (7) | |
C7 | 0.1609 (4) | 0.37748 (12) | 0.8347 (5) | 0.0331 (7) | |
C8 | 0.0343 (5) | 0.33378 (13) | 0.7547 (5) | 0.0398 (8) | |
H8A | 0.0735 | 0.3112 | 0.6752 | 0.048* | |
H8B | −0.0891 | 0.3447 | 0.6675 | 0.048* | |
C9 | 0.0472 (4) | 0.30873 (13) | 0.9553 (5) | 0.0373 (8) | |
H9 | 0.0792 | 0.2734 | 0.9553 | 0.045* | |
C10 | −0.1191 (4) | 0.31280 (12) | 0.9911 (5) | 0.0355 (8) | |
C11 | −0.2383 (5) | 0.27922 (15) | 0.9944 (6) | 0.0470 (9) | |
H11 | −0.2315 | 0.2448 | 0.9813 | 0.056* | |
C12 | −0.3780 (5) | 0.30560 (16) | 1.0217 (6) | 0.0535 (10) | |
H12 | −0.4796 | 0.2920 | 1.0306 | 0.064* | |
C13 | −0.3341 (5) | 0.35353 (17) | 1.0319 (6) | 0.0521 (10) | |
H13 | −0.4020 | 0.3794 | 1.0501 | 0.063* | |
C14 | 0.3013 (5) | 0.32032 (15) | 1.3154 (6) | 0.0440 (9) | |
C15 | 0.4664 (5) | 0.34952 (16) | 1.4508 (6) | 0.0531 (10) | |
H15A | 0.5274 | 0.3332 | 1.5835 | 0.080* | |
H15B | 0.4309 | 0.3825 | 1.4712 | 0.080* | |
H15C | 0.5472 | 0.3517 | 1.3847 | 0.080* | |
N1 | 0.2571 (4) | 0.37738 (10) | 1.0338 (4) | 0.0350 (7) | |
N2 | 0.2051 (4) | 0.33615 (10) | 1.1156 (4) | 0.0367 (7) | |
O1 | −0.1747 (3) | 0.35984 (9) | 1.0122 (4) | 0.0475 (6) | |
O2 | 0.2510 (4) | 0.28316 (11) | 1.3765 (5) | 0.0643 (8) | |
Br1 | 0.23278 (6) | 0.540128 (15) | 0.26614 (7) | 0.0570 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.041 (2) | 0.042 (2) | 0.040 (2) | −0.0056 (16) | 0.0150 (17) | −0.0054 (15) |
C2 | 0.049 (2) | 0.055 (2) | 0.033 (2) | 0.0008 (18) | 0.0177 (18) | −0.0001 (16) |
C3 | 0.0306 (18) | 0.044 (2) | 0.045 (2) | 0.0050 (15) | 0.0202 (17) | 0.0076 (15) |
C4 | 0.045 (2) | 0.046 (2) | 0.050 (2) | −0.0078 (18) | 0.0164 (19) | −0.0002 (17) |
C5 | 0.045 (2) | 0.049 (2) | 0.036 (2) | −0.0021 (17) | 0.0113 (18) | 0.0000 (16) |
C6 | 0.0237 (16) | 0.0426 (19) | 0.0336 (18) | 0.0033 (14) | 0.0115 (14) | −0.0002 (14) |
C7 | 0.0257 (17) | 0.0385 (19) | 0.036 (2) | 0.0038 (14) | 0.0138 (15) | −0.0005 (14) |
C8 | 0.038 (2) | 0.042 (2) | 0.041 (2) | −0.0011 (16) | 0.0185 (17) | −0.0042 (15) |
C9 | 0.0318 (19) | 0.0380 (19) | 0.042 (2) | −0.0008 (15) | 0.0159 (16) | −0.0005 (15) |
C10 | 0.0321 (18) | 0.0379 (19) | 0.0329 (18) | 0.0024 (15) | 0.0105 (15) | 0.0013 (14) |
C11 | 0.038 (2) | 0.042 (2) | 0.061 (3) | −0.0017 (17) | 0.0208 (19) | 0.0065 (17) |
C12 | 0.035 (2) | 0.069 (3) | 0.059 (3) | 0.000 (2) | 0.0223 (19) | 0.013 (2) |
C13 | 0.038 (2) | 0.072 (3) | 0.053 (2) | 0.013 (2) | 0.0256 (19) | −0.0008 (19) |
C14 | 0.0339 (19) | 0.057 (2) | 0.042 (2) | 0.0057 (17) | 0.0179 (17) | 0.0104 (17) |
C15 | 0.035 (2) | 0.076 (3) | 0.040 (2) | −0.0051 (19) | 0.0084 (18) | 0.0077 (19) |
N1 | 0.0277 (15) | 0.0415 (17) | 0.0363 (17) | 0.0012 (12) | 0.0142 (13) | 0.0030 (12) |
N2 | 0.0264 (14) | 0.0425 (17) | 0.0372 (17) | −0.0024 (13) | 0.0098 (13) | 0.0052 (13) |
O1 | 0.0433 (15) | 0.0425 (15) | 0.0624 (17) | 0.0000 (12) | 0.0282 (13) | −0.0055 (12) |
O2 | 0.0591 (19) | 0.072 (2) | 0.0582 (18) | −0.0086 (15) | 0.0221 (15) | 0.0243 (15) |
Br1 | 0.0593 (3) | 0.0572 (3) | 0.0622 (3) | 0.0015 (2) | 0.0335 (2) | 0.01656 (19) |
C1—C2 | 1.379 (5) | C9—N2 | 1.490 (4) |
C1—C6 | 1.380 (5) | C9—H9 | 0.9800 |
C1—H1 | 0.9300 | C10—C11 | 1.330 (5) |
C2—C3 | 1.383 (5) | C10—O1 | 1.367 (4) |
C2—H2 | 0.9300 | C11—C12 | 1.421 (5) |
C3—C4 | 1.370 (5) | C11—H11 | 0.9300 |
C3—Br1 | 1.898 (3) | C12—C13 | 1.325 (6) |
C4—C5 | 1.382 (5) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—O1 | 1.375 (4) |
C5—C6 | 1.396 (5) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—O2 | 1.224 (4) |
C6—C7 | 1.467 (5) | C14—N2 | 1.358 (5) |
C7—N1 | 1.287 (4) | C14—C15 | 1.492 (5) |
C7—C8 | 1.499 (5) | C15—H15A | 0.9600 |
C8—C9 | 1.535 (5) | C15—H15B | 0.9600 |
C8—H8A | 0.9700 | C15—H15C | 0.9600 |
C8—H8B | 0.9700 | N1—N2 | 1.395 (4) |
C9—C10 | 1.486 (5) | ||
C2—C1—C6 | 121.7 (3) | C10—C9—H9 | 109.4 |
C2—C1—H1 | 119.1 | N2—C9—H9 | 109.4 |
C6—C1—H1 | 119.1 | C8—C9—H9 | 109.4 |
C1—C2—C3 | 118.6 (3) | C11—C10—O1 | 110.0 (3) |
C1—C2—H2 | 120.7 | C11—C10—C9 | 132.8 (3) |
C3—C2—H2 | 120.7 | O1—C10—C9 | 117.1 (3) |
C4—C3—C2 | 121.0 (3) | C10—C11—C12 | 107.4 (4) |
C4—C3—Br1 | 119.9 (3) | C10—C11—H11 | 126.3 |
C2—C3—Br1 | 119.1 (3) | C12—C11—H11 | 126.3 |
C3—C4—C5 | 120.0 (3) | C13—C12—C11 | 106.0 (3) |
C3—C4—H4 | 120.0 | C13—C12—H12 | 127.0 |
C5—C4—H4 | 120.0 | C11—C12—H12 | 127.0 |
C4—C5—C6 | 120.0 (3) | C12—C13—O1 | 111.0 (3) |
C4—C5—H5 | 120.0 | C12—C13—H13 | 124.5 |
C6—C5—H5 | 120.0 | O1—C13—H13 | 124.5 |
C1—C6—C5 | 118.6 (3) | O2—C14—N2 | 119.5 (4) |
C1—C6—C7 | 120.3 (3) | O2—C14—C15 | 122.9 (4) |
C5—C6—C7 | 121.1 (3) | N2—C14—C15 | 117.5 (3) |
N1—C7—C6 | 122.1 (3) | C14—C15—H15A | 109.5 |
N1—C7—C8 | 114.0 (3) | C14—C15—H15B | 109.5 |
C6—C7—C8 | 123.9 (3) | H15A—C15—H15B | 109.5 |
C7—C8—C9 | 103.3 (3) | C14—C15—H15C | 109.5 |
C7—C8—H8A | 111.1 | H15A—C15—H15C | 109.5 |
C9—C8—H8A | 111.1 | H15B—C15—H15C | 109.5 |
C7—C8—H8B | 111.1 | C7—N1—N2 | 108.0 (3) |
C9—C8—H8B | 111.1 | C14—N2—N1 | 122.6 (3) |
H8A—C8—H8B | 109.1 | C14—N2—C9 | 124.2 (3) |
C10—C9—N2 | 112.5 (3) | N1—N2—C9 | 112.9 (3) |
C10—C9—C8 | 115.1 (3) | C10—O1—C13 | 105.6 (3) |
N2—C9—C8 | 100.6 (3) | ||
C6—C1—C2—C3 | −0.1 (6) | C8—C9—C10—O1 | −61.3 (4) |
C1—C2—C3—C4 | −0.6 (6) | O1—C10—C11—C12 | −0.8 (4) |
C1—C2—C3—Br1 | −179.2 (3) | C9—C10—C11—C12 | −175.8 (4) |
C2—C3—C4—C5 | 0.4 (6) | C10—C11—C12—C13 | 0.3 (4) |
Br1—C3—C4—C5 | 179.0 (3) | C11—C12—C13—O1 | 0.2 (5) |
C3—C4—C5—C6 | 0.4 (6) | C6—C7—N1—N2 | 178.7 (3) |
C2—C1—C6—C5 | 0.9 (5) | C8—C7—N1—N2 | −2.5 (4) |
C2—C1—C6—C7 | −179.5 (3) | O2—C14—N2—N1 | −178.3 (3) |
C4—C5—C6—C1 | −1.1 (5) | C15—C14—N2—N1 | 1.4 (5) |
C4—C5—C6—C7 | 179.4 (3) | O2—C14—N2—C9 | −5.3 (5) |
C1—C6—C7—N1 | 170.1 (3) | C15—C14—N2—C9 | 174.3 (3) |
C5—C6—C7—N1 | −10.4 (5) | C7—N1—N2—C14 | 168.2 (3) |
C1—C6—C7—C8 | −8.5 (5) | C7—N1—N2—C9 | −5.5 (4) |
C5—C6—C7—C8 | 171.0 (3) | C10—C9—N2—C14 | 73.8 (4) |
N1—C7—C8—C9 | 8.9 (4) | C8—C9—N2—C14 | −163.2 (3) |
C6—C7—C8—C9 | −172.4 (3) | C10—C9—N2—N1 | −112.6 (3) |
C7—C8—C9—C10 | 110.6 (3) | C8—C9—N2—N1 | 10.4 (3) |
C7—C8—C9—N2 | −10.6 (3) | C11—C10—O1—C13 | 0.9 (4) |
N2—C9—C10—C11 | −132.1 (4) | C9—C10—O1—C13 | 176.8 (3) |
C8—C9—C10—C11 | 113.5 (4) | C12—C13—O1—C10 | −0.7 (4) |
N2—C9—C10—O1 | 53.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.98 | 2.29 | 3.148 (4) | 146 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13BrN2O2 |
Mr | 333.18 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 8.1417 (17), 26.757 (6), 7.0974 (15) |
β (°) | 115.587 (2) |
V (Å3) | 1394.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.95 |
Crystal size (mm) | 0.49 × 0.36 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.326, 0.757 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5796, 2461, 1948 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.119, 1.05 |
No. of reflections | 2461 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.43 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.98 | 2.29 | 3.148 (4) | 146 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds which possess anti-viral (Rawal et al., 1963), anti-fungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Further, 1-acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit monoamine oxidases (Manna et al., 2002). As part of our on-going investgation of pyrazolines and their metal complexes, we report here the crystal structure of the title compound (I).
In the structure of (I) (Fig. 1), all bond lengths and angles fall in the normal range (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by the pyrazolinyl ring with the phenyl and furan rings are 11.3 (2) and 88.0 (2)°, respectively. There are some intermolecular C—H···O contacts (Table 1) which stabilize the structure.