1,5-Di­methyl-4-[(4-nitro­benzyl­idene)­amino]-2-phenyl-2,3-di­hydro-1H-pyrazol-3-one

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)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

---

Computing details

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-1H- pyrazol-3-one

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.232	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0564P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O3^i	0.93	2.55	3.479 (9)	175
C11—H11···O1^ii	0.93	2.52	3.225 (8)	133

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z+1.