3-(2-Furyl)-1-phenylprop-2-en-1-one 2,4-dinitro­phenyl­hydrazone

In the title compound, C₁₉H₁₄N₄O₅, the dinitro­phenyl­hydrazone and furylidene groups are nearly coplanar, making a dihedral angle of 4.50 (10)°. There is an intra­molecular N—H...O hydrogen bond, while weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into pseudo-dimers arranged around inversion centers.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.135
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C16    -   C17     ..       7.03 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT074_ALERT_1_C Occupancy Parameter = 0.0 for ..................        CG1
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit    - p 2yn
PLAT213_ALERT_2_C Atom O2      has ADP max/min Ratio .............       3.10 prolat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.16

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

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Furylideneacetophenone 2,4-dinitrophenylhydrazone

Crystal data

C19H14N4O5	F(000) = 784
Mr = 378.34	Dx = 1.379 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: - P 2yn	Cell parameters from 4026 reflections
a = 8.1605 (5) Å	θ = 2.8–27.3°
b = 17.7094 (11) Å	µ = 0.10 mm^−1
c = 12.8041 (8) Å	T = 291 K
β = 100.058 (1)°	Block, brown
V = 1822.0 (2) Å^3	0.37 × 0.30 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4181 independent reflections
Radiation source: fine-focus sealed tube	2780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.963, Tmax = 0.978	k = −23→22
15658 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 0.2674P] where P = (Fo^2 + 2Fc^2)/3
4181 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.23 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	Occ. (<1)
O1	−0.2015 (2)	0.67948 (8)	0.72120 (17)	0.1226 (7)
O2	−0.1931 (3)	0.79863 (9)	0.7206 (2)	0.1549 (10)
O3	0.21815 (17)	0.93777 (7)	0.58948 (11)	0.0759 (4)
O4	0.40617 (16)	0.88133 (7)	0.52170 (12)	0.0831 (4)
O5	0.23793 (14)	0.26020 (6)	0.58043 (10)	0.0681 (3)
N1	−0.1333 (2)	0.73854 (9)	0.70425 (16)	0.0879 (6)
N2	0.28778 (17)	0.88018 (7)	0.56792 (11)	0.0573 (3)
N3	0.03351 (16)	0.60023 (7)	0.66072 (11)	0.0564 (3)
H3	−0.0578	0.5984	0.6855	0.068*
N4	0.10987 (15)	0.53411 (7)	0.64051 (11)	0.0526 (3)
C1	0.09817 (18)	0.66797 (8)	0.64275 (12)	0.0487 (3)
C2	0.0196 (2)	0.73669 (9)	0.66155 (13)	0.0554 (4)
C3	0.08410 (19)	0.80575 (8)	0.63923 (12)	0.0537 (4)
H3A	0.0313	0.8503	0.6529	0.064*
C4	0.22599 (18)	0.80770 (8)	0.59697 (12)	0.0489 (3)
C5	0.31055 (19)	0.74168 (9)	0.57968 (13)	0.0553 (4)
H5	0.4087	0.7441	0.5523	0.066*
C6	0.24824 (19)	0.67373 (8)	0.60324 (13)	0.0537 (4)
H6	0.3063	0.6299	0.5930	0.064*
C7	0.02837 (17)	0.47320 (8)	0.65660 (12)	0.0463 (3)
C8	0.09989 (18)	0.40185 (8)	0.63386 (12)	0.0502 (4)
H8	0.1988	0.4027	0.6072	0.060*
C9	0.03328 (18)	0.33467 (8)	0.64856 (12)	0.0471 (3)
H9	−0.0644	0.3347	0.6767	0.056*
C10	0.09750 (18)	0.26246 (8)	0.62525 (12)	0.0489 (3)
C11	0.0458 (2)	0.19126 (8)	0.63888 (13)	0.0569 (4)
H11	−0.0469	0.1773	0.6676	0.068*
C12	0.1585 (2)	0.14190 (10)	0.60134 (15)	0.0699 (5)
H12	0.1549	0.0894	0.6005	0.084*
C13	0.2704 (3)	0.18551 (11)	0.56768 (17)	0.0773 (6)
H13	0.3599	0.1675	0.5389	0.093*
C14	−0.13698 (17)	0.47572 (7)	0.69188 (12)	0.0449 (3)
C15	−0.1521 (2)	0.48766 (9)	0.79639 (13)	0.0579 (4)
H15	−0.0576	0.4921	0.8484	0.070*
C16	−0.3102 (2)	0.49308 (10)	0.82338 (15)	0.0670 (5)
H16	−0.3206	0.5003	0.8939	0.080*
C17	−0.4499 (2)	0.48794 (10)	0.74736 (16)	0.0665 (5)
H17	−0.5547	0.4922	0.7659	0.080*
C18	−0.4345 (2)	0.47654 (11)	0.64472 (16)	0.0730 (5)
H18	−0.5295	0.4729	0.5929	0.088*
C19	−0.2795 (2)	0.47029 (10)	0.61636 (13)	0.0607 (4)
H19	−0.2710	0.4624	0.5457	0.073*
CG1	−0.2939	0.4819	0.7200	0.010*	0.00

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1093 (12)	0.0565 (8)	0.235 (2)	0.0023 (8)	0.1207 (14)	0.0107 (10)
O2	0.1618 (17)	0.0542 (9)	0.298 (3)	0.0153 (9)	0.1780 (19)	0.0024 (12)
O3	0.0961 (9)	0.0429 (6)	0.1003 (10)	0.0039 (6)	0.0492 (8)	0.0009 (6)
O4	0.0796 (9)	0.0614 (8)	0.1231 (12)	−0.0062 (6)	0.0582 (8)	0.0032 (7)
O5	0.0601 (7)	0.0544 (7)	0.0986 (9)	0.0070 (5)	0.0387 (6)	−0.0018 (6)
N1	0.0903 (12)	0.0500 (9)	0.1441 (16)	0.0078 (8)	0.0780 (12)	0.0049 (9)
N2	0.0624 (8)	0.0469 (7)	0.0674 (8)	−0.0033 (6)	0.0248 (7)	−0.0017 (6)
N3	0.0497 (7)	0.0395 (7)	0.0855 (10)	0.0003 (5)	0.0272 (7)	−0.0028 (6)
N4	0.0450 (7)	0.0404 (7)	0.0752 (9)	0.0009 (5)	0.0180 (6)	−0.0038 (6)
C1	0.0478 (8)	0.0406 (7)	0.0597 (9)	−0.0010 (6)	0.0152 (7)	−0.0040 (6)
C2	0.0558 (9)	0.0453 (8)	0.0721 (10)	0.0028 (7)	0.0302 (8)	−0.0016 (7)
C3	0.0617 (10)	0.0404 (8)	0.0641 (10)	0.0035 (7)	0.0256 (8)	−0.0029 (7)
C4	0.0535 (9)	0.0413 (8)	0.0541 (8)	−0.0039 (6)	0.0153 (7)	−0.0024 (6)
C5	0.0464 (8)	0.0513 (9)	0.0721 (10)	−0.0026 (6)	0.0212 (7)	−0.0059 (7)
C6	0.0475 (8)	0.0421 (8)	0.0745 (10)	0.0013 (6)	0.0192 (7)	−0.0074 (7)
C7	0.0406 (7)	0.0422 (8)	0.0567 (8)	0.0004 (6)	0.0102 (6)	−0.0019 (6)
C8	0.0398 (7)	0.0458 (8)	0.0674 (10)	0.0021 (6)	0.0157 (7)	−0.0040 (7)
C9	0.0439 (8)	0.0447 (8)	0.0544 (8)	0.0021 (6)	0.0137 (6)	−0.0029 (6)
C10	0.0460 (8)	0.0470 (8)	0.0562 (9)	0.0033 (6)	0.0160 (7)	−0.0012 (6)
C11	0.0644 (10)	0.0452 (8)	0.0640 (10)	0.0008 (7)	0.0192 (8)	−0.0007 (7)
C12	0.0875 (13)	0.0461 (9)	0.0791 (12)	0.0132 (9)	0.0225 (10)	−0.0019 (8)
C13	0.0774 (12)	0.0616 (11)	0.1007 (15)	0.0213 (9)	0.0371 (11)	−0.0057 (10)
C14	0.0452 (8)	0.0361 (7)	0.0554 (8)	0.0014 (5)	0.0144 (6)	−0.0004 (6)
C15	0.0630 (10)	0.0547 (9)	0.0570 (9)	0.0000 (7)	0.0132 (8)	−0.0045 (7)
C16	0.0878 (13)	0.0575 (10)	0.0647 (11)	0.0011 (9)	0.0380 (10)	−0.0020 (8)
C17	0.0548 (10)	0.0625 (10)	0.0898 (13)	0.0036 (8)	0.0338 (10)	0.0085 (9)
C18	0.0454 (9)	0.0975 (15)	0.0772 (12)	−0.0002 (9)	0.0137 (8)	0.0064 (10)
C19	0.0475 (9)	0.0779 (12)	0.0584 (10)	0.0004 (8)	0.0138 (7)	−0.0019 (8)

Geometric parameters (Å, º)

O1—N1	1.2218 (19)	C7—C14	1.4965 (19)
O2—N1	1.204 (2)	C8—C9	1.3348 (19)
O3—N2	1.2223 (16)	C8—H8	0.9300
O4—N2	1.2181 (17)	C9—C10	1.4332 (19)
O5—C13	1.364 (2)	C9—H9	0.9300
O5—C10	1.3690 (18)	C10—C11	1.351 (2)
N1—C2	1.448 (2)	C11—C12	1.413 (2)
N2—C4	1.4511 (18)	C11—H11	0.9300
N3—C1	1.3464 (18)	C12—C13	1.324 (3)
N3—N4	1.3722 (16)	C12—H12	0.9300
N3—H3	0.8600	C13—H13	0.9300
N4—C7	1.3024 (18)	C14—C19	1.380 (2)
C1—C6	1.408 (2)	C14—C15	1.381 (2)
C1—C2	1.4156 (19)	C15—C16	1.396 (2)
C2—C3	1.381 (2)	C15—H15	0.9300
C3—C4	1.361 (2)	C16—C17	1.366 (3)
C3—H3A	0.9300	C16—H16	0.9300
C4—C5	1.395 (2)	C17—C18	1.357 (3)
C5—C6	1.361 (2)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.380 (2)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.4426 (19)	C19—H19	0.9300
C13—O5—C10	105.82 (13)	C7—C8—H8	117.9
O2—N1—O1	120.97 (16)	C8—C9—C10	126.38 (13)
O2—N1—C2	119.20 (15)	C8—C9—H9	116.8
O1—N1—C2	119.81 (14)	C10—C9—H9	116.8
O4—N2—O3	122.36 (13)	C11—C10—O5	109.29 (13)
O4—N2—C4	118.68 (13)	C11—C10—C9	132.24 (14)
O3—N2—C4	118.96 (12)	O5—C10—C9	118.47 (13)
C1—N3—N4	121.58 (12)	C10—C11—C12	107.26 (15)
C1—N3—H3	119.2	C10—C11—H11	126.4
N4—N3—H3	119.2	C12—C11—H11	126.4
C7—N4—N3	114.56 (12)	C13—C12—C11	106.08 (16)
N3—C1—C6	121.16 (13)	C13—C12—H12	127.0
N3—C1—C2	122.30 (13)	C11—C12—H12	127.0
C6—C1—C2	116.54 (13)	C12—C13—O5	111.55 (15)
C3—C2—C1	121.74 (14)	C12—C13—H13	124.2
C3—C2—N1	116.29 (13)	O5—C13—H13	124.2
C1—C2—N1	121.97 (13)	C19—C14—C15	118.84 (14)
C4—C3—C2	119.07 (13)	C19—C14—C7	118.71 (13)
C4—C3—H3A	120.5	C15—C14—C7	122.34 (14)
C2—C3—H3A	120.5	C14—C15—C16	119.55 (16)
C3—C4—C5	121.37 (13)	C14—C15—H15	120.2
C3—C4—N2	118.81 (13)	C16—C15—H15	120.2
C5—C4—N2	119.81 (13)	C17—C16—C15	120.73 (16)
C6—C5—C4	119.46 (14)	C17—C16—H16	119.6
C6—C5—H5	120.3	C15—C16—H16	119.6
C4—C5—H5	120.3	C18—C17—C16	119.56 (16)
C5—C6—C1	121.73 (14)	C18—C17—H17	120.2
C5—C6—H6	119.1	C16—C17—H17	120.2
C1—C6—H6	119.1	C17—C18—C19	120.71 (18)
N4—C7—C8	117.24 (13)	C17—C18—H18	119.6
N4—C7—C14	122.36 (12)	C19—C18—H18	119.6
C8—C7—C14	120.33 (12)	C14—C19—C18	120.61 (16)
C9—C8—C7	124.27 (13)	C14—C19—H19	119.7
C9—C8—H8	117.9	C18—C19—H19	119.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	1.96	2.6014 (18)	131
C13—H13···O4^i	0.93	2.35	3.276 (2)	176

Symmetry code: (i) −x+1, −y+1, −z+1.