In the title compound, C
19H
14N
4O
5, 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.
Supporting information
CCDC reference: 605057
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.37 × 0.30 × 0.22 mm |
Z = 4 | |
Data collection top
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 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.2674P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O4i | 0.93 | 2.35 | 3.276 (2) | 176 |
Symmetry code: (i) −x+1, −y+1, −z+1. |