5-(2-Fur­yl)-3-methyl-1-(4-nitro­phen­yl)-2-pyrazoline

In the title compound, C₁₄H₁₃N₃O₃, the pyrazoline ring and the 4-nitro­phenyl group are nearly coplanar, whereas the furyl and pyrazoline rings are roughly perpendicular. The occurrence of weak C—H...O hydrogen-bonding inter­actions results in the formation of an R₃³(15) ring.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.50
           From the CIF: _reflns_number_total               1470
           Count of symmetry unique reflns         1471
           Completeness (_total/calc)             99.93%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-(2-Furyl)-3-methyl-1-(4-nitrophenyl)-2-pyrazoline

Crystal data

C14H13N3O3	F(000) = 284
Mr = 271.27	Dx = 1.361 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1202 reflections
a = 8.1504 (13) Å	θ = 2.5–23.3°
b = 8.4608 (14) Å	µ = 0.10 mm^−1
c = 9.6959 (16) Å	T = 298 K
β = 98.036 (2)°	Block, brown
V = 662.05 (19) Å^3	0.27 × 0.23 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1470 independent reflections
Radiation source: fine-focus sealed tube	1047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan SADABS(Bruker, 2000)	h = −10→10
Tmin = 0.974, Tmax = 0.981	k = −10→10
5482 measured reflections	l = 0→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.0117P] where P = (Fo^2 + 2Fc^2)/3
1470 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.10 e Å^−3
1 restraint	Δρmin = −0.15 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
O1	0.5650 (3)	0.1026 (3)	0.6998 (2)	0.0706 (7)
O2	0.0242 (3)	0.8511 (3)	0.7828 (3)	0.0751 (7)
O3	−0.0340 (4)	0.6890 (3)	0.9423 (2)	0.0860 (8)
N1	0.0164 (3)	0.7168 (3)	0.8302 (3)	0.0587 (7)
N2	0.2498 (3)	0.2093 (3)	0.5444 (2)	0.0467 (6)
N3	0.3052 (3)	0.2307 (3)	0.4153 (2)	0.0470 (6)
C1	0.0679 (3)	0.5841 (3)	0.7517 (3)	0.0444 (7)
C2	0.0706 (3)	0.4349 (3)	0.8086 (3)	0.0481 (8)
H2	0.0340	0.4191	0.8943	0.058*
C3	0.1272 (3)	0.3094 (3)	0.7391 (3)	0.0459 (7)
H3	0.1269	0.2084	0.7768	0.055*
C4	0.1861 (3)	0.3332 (3)	0.6101 (3)	0.0409 (6)
C5	0.1759 (3)	0.4849 (3)	0.5516 (3)	0.0456 (7)
H5	0.2079	0.5015	0.4644	0.055*
C6	0.1184 (3)	0.6096 (4)	0.6229 (3)	0.0490 (7)
H6	0.1136	0.7106	0.5847	0.059*
C7	0.3484 (3)	0.0957 (4)	0.3743 (3)	0.0492 (7)
C8	0.4114 (4)	0.0739 (5)	0.2378 (3)	0.0684 (10)
H8A	0.4129	0.1741	0.1914	0.103*
H8B	0.3401	0.0023	0.1807	0.103*
H8C	0.5217	0.0314	0.2537	0.103*
C9	0.3254 (4)	−0.0376 (4)	0.4704 (3)	0.0541 (7)
H9A	0.4263	−0.0989	0.4919	0.065*
H9B	0.2363	−0.1068	0.4308	0.065*
C10	0.2817 (3)	0.0480 (3)	0.6003 (3)	0.0452 (7)
H10	0.1796	0.0036	0.6269	0.054*
C11	0.4144 (4)	0.0454 (4)	0.7218 (3)	0.0500 (7)
C12	0.4213 (4)	−0.0061 (5)	0.8515 (3)	0.0784 (11)
H12	0.3346	−0.0493	0.8920	0.094*
C13	0.5876 (4)	0.0175 (6)	0.9171 (4)	0.0973 (15)
H13	0.6311	−0.0085	1.0081	0.117*
C14	0.6670 (4)	0.0834 (6)	0.8226 (4)	0.0900 (14)
H14	0.7780	0.1130	0.8377	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0502 (13)	0.0989 (18)	0.0614 (13)	−0.0039 (13)	0.0037 (10)	−0.0058 (13)
O2	0.0760 (16)	0.0480 (14)	0.105 (2)	−0.0017 (12)	0.0252 (14)	−0.0099 (15)
O3	0.120 (2)	0.0822 (18)	0.0607 (15)	0.0105 (16)	0.0309 (14)	−0.0167 (14)
N1	0.0549 (15)	0.0569 (19)	0.0633 (17)	0.0020 (15)	0.0052 (13)	−0.0126 (16)
N2	0.0534 (14)	0.0441 (14)	0.0441 (13)	0.0043 (12)	0.0122 (11)	0.0035 (12)
N3	0.0456 (13)	0.0543 (16)	0.0425 (13)	0.0008 (12)	0.0116 (10)	0.0013 (12)
C1	0.0424 (15)	0.0454 (18)	0.0446 (16)	−0.0008 (13)	0.0035 (12)	−0.0057 (14)
C2	0.0474 (16)	0.055 (2)	0.0417 (15)	0.0026 (14)	0.0075 (12)	−0.0012 (15)
C3	0.0492 (17)	0.0421 (17)	0.0470 (17)	−0.0010 (14)	0.0090 (13)	0.0060 (14)
C4	0.0374 (15)	0.0425 (15)	0.0417 (15)	0.0001 (12)	0.0022 (12)	−0.0026 (13)
C5	0.0427 (15)	0.0492 (19)	0.0458 (15)	−0.0003 (14)	0.0089 (12)	0.0072 (15)
C6	0.0460 (15)	0.0452 (18)	0.0548 (18)	0.0028 (14)	0.0035 (13)	0.0064 (16)
C7	0.0422 (15)	0.061 (2)	0.0448 (16)	−0.0012 (15)	0.0070 (12)	−0.0026 (15)
C8	0.067 (2)	0.084 (3)	0.0563 (19)	0.0092 (19)	0.0174 (16)	−0.0071 (19)
C9	0.0559 (17)	0.0557 (19)	0.0492 (16)	0.0058 (15)	0.0018 (13)	−0.0052 (16)
C10	0.0463 (15)	0.0428 (16)	0.0462 (16)	0.0022 (13)	0.0050 (12)	0.0012 (13)
C11	0.0486 (16)	0.0566 (19)	0.0448 (15)	0.0075 (14)	0.0069 (12)	0.0006 (14)
C12	0.058 (2)	0.122 (3)	0.0544 (18)	0.006 (2)	0.0036 (15)	0.015 (2)
C13	0.066 (2)	0.171 (5)	0.051 (2)	0.031 (3)	−0.0082 (18)	−0.007 (3)
C14	0.053 (2)	0.147 (4)	0.067 (2)	0.008 (2)	−0.0031 (18)	−0.027 (3)

Geometric parameters (Å, º)

O1—C14	1.364 (4)	C6—H6	0.9300
O1—C11	1.364 (4)	C7—C9	1.491 (4)
O2—N1	1.231 (4)	C7—C8	1.497 (4)
O3—N1	1.236 (3)	C8—H8A	0.9600
N1—C1	1.451 (4)	C8—H8B	0.9600
N2—C4	1.366 (3)	C8—H8C	0.9600
N2—N3	1.400 (3)	C9—C10	1.538 (4)
N2—C10	1.478 (4)	C9—H9A	0.9700
N3—C7	1.275 (4)	C9—H9B	0.9700
C1—C2	1.377 (4)	C10—C11	1.483 (4)
C1—C6	1.385 (4)	C10—H10	0.9800
C2—C3	1.372 (4)	C11—C12	1.325 (4)
C2—H2	0.9300	C12—C13	1.429 (5)
C3—C4	1.415 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.317 (5)
C4—C5	1.401 (4)	C13—H13	0.9300
C5—C6	1.379 (4)	C14—H14	0.9300
C5—H5	0.9300
C14—O1—C11	105.8 (3)	C7—C8—H8B	109.5
O2—N1—O3	123.0 (3)	H8A—C8—H8B	109.5
O2—N1—C1	119.0 (3)	C7—C8—H8C	109.5
O3—N1—C1	118.0 (3)	H8A—C8—H8C	109.5
C4—N2—N3	120.6 (2)	H8B—C8—H8C	109.5
C4—N2—C10	126.6 (2)	C7—C9—C10	102.7 (2)
N3—N2—C10	112.6 (2)	C7—C9—H9A	111.2
C7—N3—N2	107.5 (2)	C10—C9—H9A	111.2
C2—C1—C6	120.9 (3)	C7—C9—H9B	111.2
C2—C1—N1	119.2 (3)	C10—C9—H9B	111.2
C6—C1—N1	119.8 (3)	H9A—C9—H9B	109.1
C3—C2—C1	120.0 (2)	N2—C10—C11	112.1 (2)
C3—C2—H2	120.0	N2—C10—C9	100.6 (2)
C1—C2—H2	120.0	C11—C10—C9	114.6 (2)
C2—C3—C4	120.2 (3)	N2—C10—H10	109.7
C2—C3—H3	119.9	C11—C10—H10	109.7
C4—C3—H3	119.9	C9—C10—H10	109.7
N2—C4—C5	121.3 (2)	C12—C11—O1	110.2 (3)
N2—C4—C3	120.1 (3)	C12—C11—C10	133.5 (3)
C5—C4—C3	118.7 (3)	O1—C11—C10	116.3 (2)
C6—C5—C4	120.2 (2)	C11—C12—C13	106.8 (3)
C6—C5—H5	119.9	C11—C12—H12	126.6
C4—C5—H5	119.9	C13—C12—H12	126.6
C5—C6—C1	119.8 (3)	C14—C13—C12	106.1 (3)
C5—C6—H6	120.1	C14—C13—H13	127.0
C1—C6—H6	120.1	C12—C13—H13	127.0
N3—C7—C9	114.7 (2)	C13—C14—O1	111.1 (3)
N3—C7—C8	122.0 (3)	C13—C14—H14	124.5
C9—C7—C8	123.2 (3)	O1—C14—H14	124.5
C7—C8—H8A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.93	2.51	3.233 (4)	135
C10—H10···O2^ii	0.98	2.47	3.369 (4)	153

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x, y−1, z.