In the title molecule, C18H16N4O3, the substituted p-nitrophenyl ring is almost coplanar with the pyrazoline ring [dihedral angle = 8.2 (4)°], whereas the phenyl ring directly attached to the pyrazoline ring forms a dihedral angle of 54.5 (2)°.
Supporting information
CCDC reference: 259103
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.084
- wR factor = 0.232
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.02
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2703
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2869
Completeness (_total/calc) 94.21%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT213_ALERT_2_C Atom O1 has ADP max/min Ratio ............. 3.20 oblate
PLAT213_ALERT_2_C Atom N1 has ADP max/min Ratio ............. 3.60 oblate
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.35
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C13 -C18 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.
1,5-Dimethyl-4-[(4-nitrobenzylidene)amino]-2-phenyl-2,3-dihydro-1
H-
pyrazol-3-one
top
Crystal data top
C18H16N4O3 | Z = 2 |
Mr = 336.35 | F(000) = 352 |
Triclinic, P1 | Dx = 1.380 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.003 (2) Å | Cell parameters from 569 reflections |
b = 9.537 (4) Å | θ = 2.5–22.4° |
c = 12.540 (3) Å | µ = 0.10 mm−1 |
α = 100.3970 (15)° | T = 298 K |
β = 98.8080 (15)° | Needle, yellow |
γ = 94.5490 (15)° | 0.45 × 0.32 × 0.19 mm |
V = 809.2 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2703 independent reflections |
Radiation source: fine-focus sealed tube | 958 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→7 |
Tmin = 0.958, Tmax = 0.982 | k = −11→11 |
3931 measured reflections | l = −10→14 |
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)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.232 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3 |
2703 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4885 (7) | 0.1496 (5) | 0.7237 (4) | 0.0342 (13) | |
N2 | 0.6399 (7) | 0.0907 (5) | 0.6722 (4) | 0.0407 (14) | |
N3 | 0.4633 (7) | 0.2816 (5) | 0.4708 (4) | 0.0388 (14) | |
N4 | 0.1928 (10) | 0.5936 (6) | 0.0693 (5) | 0.0476 (15) | |
O1 | 0.2355 (6) | 0.2768 (4) | 0.6678 (3) | 0.0460 (12) | |
O2 | 0.0547 (8) | 0.6638 (5) | 0.0565 (4) | 0.0633 (15) | |
O3 | 0.3033 (8) | 0.5720 (6) | 0.0033 (4) | 0.0754 (17) | |
C1 | 0.3885 (10) | 0.2269 (6) | 0.6500 (5) | 0.0397 (16) | |
C2 | 0.4982 (8) | 0.2224 (6) | 0.5644 (5) | 0.0317 (15) | |
C3 | 0.6510 (9) | 0.1461 (6) | 0.5837 (5) | 0.0347 (16) | |
C4 | 0.8086 (9) | 0.1195 (7) | 0.5199 (5) | 0.0488 (18) | |
H4A | 0.8914 | 0.2072 | 0.5274 | 0.073* | |
H4B | 0.7540 | 0.0850 | 0.4437 | 0.073* | |
H4C | 0.8832 | 0.0491 | 0.5468 | 0.073* | |
C5 | 0.7977 (10) | 0.0419 (7) | 0.7423 (5) | 0.0535 (19) | |
H5A | 0.8574 | −0.0295 | 0.6984 | 0.080* | |
H5B | 0.7464 | 0.0014 | 0.7982 | 0.080* | |
H5C | 0.8930 | 0.1218 | 0.7763 | 0.080* | |
C6 | 0.3163 (9) | 0.3549 (6) | 0.4527 (4) | 0.0373 (16) | |
H6 | 0.2329 | 0.3700 | 0.5037 | 0.045* | |
C7 | 0.2825 (10) | 0.4133 (6) | 0.3528 (4) | 0.0362 (16) | |
C8 | 0.4187 (10) | 0.4107 (7) | 0.2834 (5) | 0.0450 (18) | |
H8 | 0.5339 | 0.3711 | 0.3008 | 0.054* | |
C9 | 0.3856 (10) | 0.4662 (7) | 0.1889 (5) | 0.0478 (18) | |
H9 | 0.4747 | 0.4599 | 0.1408 | 0.057* | |
C10 | 0.2211 (10) | 0.5301 (6) | 0.1668 (5) | 0.0413 (18) | |
C11 | 0.0843 (10) | 0.5359 (6) | 0.2342 (5) | 0.0473 (18) | |
H11 | −0.0299 | 0.5766 | 0.2166 | 0.057* | |
C12 | 0.1182 (10) | 0.4810 (7) | 0.3278 (5) | 0.0485 (18) | |
H12 | 0.0291 | 0.4893 | 0.3759 | 0.058* | |
C13 | 0.4010 (8) | 0.0799 (7) | 0.7964 (5) | 0.0333 (15) | |
C14 | 0.3738 (10) | −0.0652 (8) | 0.7824 (5) | 0.0495 (18) | |
H14 | 0.4162 | −0.1198 | 0.7230 | 0.059* | |
C15 | 0.2867 (11) | −0.1347 (8) | 0.8517 (6) | 0.059 (2) | |
H15 | 0.2713 | −0.2343 | 0.8407 | 0.071* | |
C16 | 0.2229 (11) | −0.0528 (10) | 0.9377 (6) | 0.060 (2) | |
H16 | 0.1613 | −0.0973 | 0.9853 | 0.072* | |
C17 | 0.2487 (10) | 0.0945 (9) | 0.9548 (5) | 0.0517 (19) | |
H17 | 0.2059 | 0.1492 | 1.0139 | 0.062* | |
C18 | 0.3387 (9) | 0.1607 (7) | 0.8834 (5) | 0.0443 (17) | |
H18 | 0.3568 | 0.2602 | 0.8945 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.011 (3) | 0.055 (3) | 0.044 (3) | 0.018 (3) | 0.010 (2) | 0.019 (3) |
N2 | 0.022 (3) | 0.053 (3) | 0.050 (3) | 0.019 (3) | 0.002 (3) | 0.015 (3) |
N3 | 0.020 (3) | 0.050 (3) | 0.049 (3) | 0.012 (3) | 0.008 (3) | 0.011 (3) |
N4 | 0.041 (4) | 0.047 (4) | 0.048 (4) | 0.002 (3) | −0.006 (3) | 0.004 (3) |
O1 | 0.017 (3) | 0.070 (3) | 0.061 (3) | 0.025 (2) | 0.012 (2) | 0.023 (2) |
O2 | 0.057 (4) | 0.059 (3) | 0.074 (4) | 0.019 (3) | −0.006 (3) | 0.024 (3) |
O3 | 0.055 (4) | 0.120 (5) | 0.068 (4) | 0.025 (3) | 0.022 (3) | 0.046 (3) |
C1 | 0.025 (4) | 0.046 (4) | 0.044 (4) | 0.006 (3) | 0.001 (3) | 0.003 (3) |
C2 | 0.013 (4) | 0.047 (4) | 0.039 (4) | 0.014 (3) | 0.009 (3) | 0.013 (3) |
C3 | 0.018 (4) | 0.049 (4) | 0.036 (4) | 0.004 (3) | 0.003 (3) | 0.006 (3) |
C4 | 0.024 (4) | 0.069 (5) | 0.056 (4) | 0.019 (4) | 0.014 (3) | 0.008 (3) |
C5 | 0.032 (5) | 0.066 (5) | 0.063 (5) | 0.022 (4) | −0.009 (3) | 0.020 (4) |
C6 | 0.037 (4) | 0.049 (4) | 0.032 (4) | 0.022 (3) | 0.009 (3) | 0.012 (3) |
C7 | 0.032 (4) | 0.042 (4) | 0.033 (4) | 0.013 (3) | 0.005 (3) | 0.000 (3) |
C8 | 0.034 (5) | 0.059 (5) | 0.046 (4) | 0.018 (4) | 0.005 (4) | 0.015 (3) |
C9 | 0.035 (5) | 0.054 (4) | 0.059 (5) | 0.019 (4) | 0.010 (4) | 0.013 (3) |
C10 | 0.046 (5) | 0.039 (4) | 0.039 (4) | 0.015 (4) | −0.003 (4) | 0.010 (3) |
C11 | 0.036 (5) | 0.055 (4) | 0.055 (5) | 0.029 (4) | 0.010 (4) | 0.011 (4) |
C12 | 0.028 (4) | 0.077 (5) | 0.048 (4) | 0.028 (4) | 0.019 (3) | 0.013 (4) |
C13 | 0.013 (4) | 0.055 (4) | 0.033 (4) | 0.008 (3) | −0.002 (3) | 0.015 (3) |
C14 | 0.044 (5) | 0.057 (5) | 0.050 (4) | 0.014 (4) | 0.009 (4) | 0.014 (4) |
C15 | 0.050 (5) | 0.062 (5) | 0.069 (5) | 0.007 (4) | 0.012 (4) | 0.020 (4) |
C16 | 0.044 (5) | 0.089 (6) | 0.052 (5) | 0.006 (5) | 0.006 (4) | 0.027 (4) |
C17 | 0.026 (4) | 0.087 (6) | 0.042 (4) | 0.016 (4) | 0.003 (3) | 0.009 (4) |
C18 | 0.033 (4) | 0.056 (5) | 0.044 (4) | 0.009 (4) | 0.003 (3) | 0.013 (4) |
Geometric parameters (Å, º) top
N1—C13 | 1.405 (7) | C7—C8 | 1.385 (8) |
N1—C1 | 1.420 (7) | C7—C12 | 1.386 (8) |
N1—N2 | 1.425 (6) | C8—C9 | 1.378 (8) |
N2—C3 | 1.322 (6) | C8—H8 | 0.93 |
N2—C5 | 1.464 (7) | C9—C10 | 1.360 (9) |
N3—C6 | 1.305 (7) | C9—H9 | 0.93 |
N3—C2 | 1.388 (7) | C10—C11 | 1.370 (8) |
N4—O3 | 1.220 (7) | C11—C12 | 1.365 (8) |
N4—O2 | 1.226 (7) | C11—H11 | 0.93 |
N4—C10 | 1.453 (7) | C12—H12 | 0.93 |
O1—C1 | 1.242 (7) | C13—C14 | 1.358 (8) |
C1—C2 | 1.409 (8) | C13—C18 | 1.368 (8) |
C2—C3 | 1.357 (8) | C14—C15 | 1.368 (8) |
C3—C4 | 1.471 (8) | C14—H14 | 0.93 |
C4—H4A | 0.96 | C15—C16 | 1.368 (9) |
C4—H4B | 0.96 | C15—H15 | 0.93 |
C4—H4C | 0.96 | C16—C17 | 1.375 (9) |
C5—H5A | 0.96 | C16—H16 | 0.93 |
C5—H5B | 0.96 | C17—C18 | 1.382 (8) |
C5—H5C | 0.96 | C17—H17 | 0.93 |
C6—C7 | 1.455 (7) | C18—H18 | 0.93 |
C6—H6 | 0.93 | | |
| | | |
C13—N1—C1 | 124.3 (5) | C8—C7—C6 | 121.1 (6) |
C13—N1—N2 | 121.0 (5) | C12—C7—C6 | 120.8 (6) |
C1—N1—N2 | 106.7 (5) | C9—C8—C7 | 120.7 (6) |
C3—N2—N1 | 108.5 (5) | C9—C8—H8 | 119.6 |
C3—N2—C5 | 127.5 (5) | C7—C8—H8 | 119.6 |
N1—N2—C5 | 117.3 (5) | C10—C9—C8 | 119.3 (6) |
C6—N3—C2 | 121.7 (5) | C10—C9—H9 | 120.4 |
O3—N4—O2 | 123.2 (6) | C8—C9—H9 | 120.4 |
O3—N4—C10 | 119.0 (7) | C9—C10—C11 | 121.4 (6) |
O2—N4—C10 | 117.8 (6) | C9—C10—N4 | 118.5 (6) |
O1—C1—C2 | 134.4 (6) | C11—C10—N4 | 120.1 (6) |
O1—C1—N1 | 120.9 (6) | C12—C11—C10 | 119.0 (6) |
C2—C1—N1 | 104.6 (5) | C12—C11—H11 | 120.5 |
C3—C2—N3 | 121.9 (5) | C10—C11—H11 | 120.5 |
C3—C2—C1 | 109.9 (5) | C11—C12—C7 | 121.4 (6) |
N3—C2—C1 | 128.2 (6) | C11—C12—H12 | 119.3 |
N2—C3—C2 | 109.5 (5) | C7—C12—H12 | 119.3 |
N2—C3—C4 | 121.6 (6) | C14—C13—C18 | 118.8 (6) |
C2—C3—C4 | 128.9 (6) | C14—C13—N1 | 122.2 (6) |
C3—C4—H4A | 109.5 | C18—C13—N1 | 119.0 (6) |
C3—C4—H4B | 109.5 | C13—C14—C15 | 122.9 (6) |
H4A—C4—H4B | 109.5 | C13—C14—H14 | 118.6 |
C3—C4—H4C | 109.5 | C15—C14—H14 | 118.6 |
H4A—C4—H4C | 109.5 | C16—C15—C14 | 117.8 (7) |
H4B—C4—H4C | 109.5 | C16—C15—H15 | 121.1 |
N2—C5—H5A | 109.5 | C14—C15—H15 | 121.1 |
N2—C5—H5B | 109.5 | C15—C16—C17 | 120.9 (7) |
H5A—C5—H5B | 109.5 | C15—C16—H16 | 119.5 |
N2—C5—H5C | 109.5 | C17—C16—H16 | 119.5 |
H5A—C5—H5C | 109.5 | C16—C17—C18 | 119.5 (7) |
H5B—C5—H5C | 109.5 | C16—C17—H17 | 120.2 |
N3—C6—C7 | 120.1 (6) | C18—C17—H17 | 120.2 |
N3—C6—H6 | 120.0 | C13—C18—C17 | 120.1 (7) |
C7—C6—H6 | 120.0 | C13—C18—H18 | 120.0 |
C8—C7—C12 | 118.0 (6) | C17—C18—H18 | 120.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.38 | 3.046 (7) | 128 |
C9—H9···O3i | 0.93 | 2.55 | 3.479 (9) | 175 |
C11—H11···O1ii | 0.93 | 2.52 | 3.225 (8) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z+1. |