Benzyl­ideneacetophenone 2,4-dinitro­phenyl­hydrazone

The title Schiff base compound, C₂₁H₁₆N₄O₄, features a crystallographically imposed planar -NH-N= linkage of an E configuration.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.120
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      28.00 Perc.

Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C17    -   C18    ...       1.38 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

Benzylideneacetophenone 2,4-dinitrophenylhydrazone

Crystal data

C21H16N4O4	F(000) = 808
Mr = 388.38	Dx = 1.369 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 3394 reflections
a = 18.570 (1) Å	θ = 2.6–24.9°
b = 6.9335 (4) Å	µ = 0.10 mm^−1
c = 14.6389 (9) Å	T = 291 K
V = 1884.8 (2) Å^3	Plate, brown
Z = 4	0.24 × 0.21 × 0.05 mm

Data collection

Bruker APEX area-detector diffractometer	1654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −24→23
16257 measured reflections	k = −8→8
2328 independent reflections	l = −18→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.176P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2328 reflections	Δρmax = 0.20 e Å^−3
209 parameters	Δρmin = −0.13 e Å^−3
19 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.32186 (10)	0.232 (3)	0.30230 (11)	0.111 (3)	0.50
O2	0.20783 (10)	0.2903 (17)	0.30459 (12)	0.089 (3)	0.50
O3	0.07269 (9)	0.243 (4)	0.57573 (12)	0.0809 (13)	0.50
O4	0.12552 (10)	0.266 (4)	0.70627 (12)	0.094 (3)	0.50
N1	0.45912 (7)	0.2500	0.50175 (10)	0.0474 (4)
N2	0.39634 (7)	0.2500	0.45172 (10)	0.0496 (4)
H2N	0.3987	0.2500	0.3930	0.059*
N3	0.26487 (10)	0.2579 (14)	0.34376 (13)	0.0751 (8)	0.50
N4	0.12686 (8)	0.2500	0.62302 (12)	0.0652 (5)
C1	0.77820 (9)	0.2500	0.42811 (13)	0.0525 (5)
H1	0.7673	0.2500	0.3661	0.063*
C2	0.84916 (10)	0.2500	0.45524 (14)	0.0624 (5)
H2	0.8856	0.2500	0.4117	0.075*
C3	0.86613 (10)	0.2500	0.54588 (15)	0.0700 (6)
H3	0.9141	0.2500	0.5643	0.084*
C4	0.81210 (11)	0.2500	0.60975 (15)	0.0787 (7)
H4	0.8237	0.2500	0.6715	0.094*
C5	0.74061 (10)	0.2500	0.58361 (13)	0.0632 (6)
H5	0.7046	0.2500	0.6278	0.076*
C6	0.72238 (9)	0.2500	0.49179 (12)	0.0447 (4)
C7	0.64876 (9)	0.2500	0.45629 (11)	0.0457 (4)
H7	0.6451	0.2500	0.3929	0.055*
C8	0.58606 (9)	0.2500	0.50060 (12)	0.0467 (4)
H8	0.5863	0.2500	0.5641	0.056*
C9	0.51754 (8)	0.2500	0.45335 (11)	0.0434 (4)
C10	0.51734 (9)	0.267 (2)	0.35093 (16)	0.0408 (16)	0.50
C11	0.5182 (6)	0.1019 (16)	0.2987 (7)	0.063 (2)	0.50
H11	0.5175	−0.0183	0.3269	0.076*	0.50
C12	0.5201 (6)	0.1143 (9)	0.2041 (6)	0.071 (2)	0.50
H12	0.5203	0.0026	0.1689	0.085*	0.50
C13	0.52174 (15)	0.2907 (11)	0.1629 (2)	0.065 (3)	0.50
H13	0.5239	0.2990	0.0996	0.079*	0.50
C14	0.5203 (6)	0.4559 (11)	0.2145 (6)	0.0647 (19)	0.50
H14	0.5210	0.5759	0.1860	0.078*	0.50
C15	0.5176 (5)	0.4442 (15)	0.3086 (5)	0.0491 (13)	0.50
H15	0.5161	0.5563	0.3434	0.059*	0.50
C16	0.33108 (9)	0.2500	0.49276 (11)	0.0446 (4)
C17	0.26585 (9)	0.2500	0.44263 (12)	0.0502 (4)
C18	0.19946 (9)	0.2500	0.48534 (12)	0.0511 (4)
H18	0.1573	0.2500	0.4511	0.061*
C19	0.19665 (9)	0.2500	0.57807 (13)	0.0514 (4)
C20	0.25923 (10)	0.2500	0.63042 (13)	0.0602 (5)
H20	0.2563	0.2500	0.6938	0.072*
C21	0.32492 (9)	0.2500	0.58868 (12)	0.0540 (5)
H21	0.3664	0.2500	0.6242	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0505 (9)	0.240 (8)	0.0431 (9)	0.009 (5)	0.0031 (7)	−0.029 (5)
O2	0.0513 (9)	0.167 (9)	0.0493 (9)	0.0121 (19)	−0.0142 (7)	0.0011 (17)
O3	0.0385 (9)	0.131 (4)	0.0729 (10)	−0.016 (6)	0.0038 (7)	0.003 (7)
O4	0.0598 (10)	0.164 (7)	0.0580 (10)	0.014 (4)	0.0154 (8)	−0.020 (5)
N1	0.0350 (7)	0.0623 (9)	0.0449 (8)	0.000	−0.0018 (6)	0.000
N2	0.0352 (7)	0.0735 (10)	0.0400 (8)	0.000	−0.0008 (6)	0.000
N3	0.0440 (9)	0.137 (2)	0.0448 (10)	0.009 (7)	−0.0049 (8)	−0.011 (6)
N4	0.0432 (9)	0.0937 (13)	0.0588 (11)	0.000	0.0083 (8)	0.000
C1	0.0429 (9)	0.0696 (12)	0.0449 (9)	0.000	0.0005 (7)	0.000
C2	0.0389 (10)	0.0822 (14)	0.0662 (13)	0.000	0.0060 (9)	0.000
C3	0.0404 (10)	0.0980 (16)	0.0716 (14)	0.000	−0.0127 (10)	0.000
C4	0.0552 (12)	0.131 (2)	0.0494 (11)	0.000	−0.0149 (9)	0.000
C5	0.0454 (10)	0.1004 (17)	0.0439 (10)	0.000	−0.0013 (8)	0.000
C6	0.0363 (8)	0.0539 (10)	0.0441 (9)	0.000	−0.0013 (7)	0.000
C7	0.0394 (9)	0.0568 (10)	0.0410 (9)	0.000	−0.0025 (7)	0.000
C8	0.0397 (9)	0.0591 (11)	0.0412 (9)	0.000	−0.0021 (7)	0.000
C9	0.0390 (9)	0.0494 (9)	0.0419 (9)	0.000	0.0019 (7)	0.000
C10	0.0299 (8)	0.049 (5)	0.0436 (9)	−0.004 (2)	0.0000 (7)	−0.006 (3)
C11	0.064 (3)	0.055 (5)	0.070 (4)	0.001 (2)	0.002 (2)	0.001 (2)
C12	0.071 (3)	0.084 (7)	0.058 (3)	0.003 (4)	−0.005 (3)	−0.025 (4)
C13	0.0402 (12)	0.114 (10)	0.0422 (14)	−0.0014 (19)	−0.0004 (10)	−0.003 (2)
C14	0.054 (2)	0.084 (5)	0.055 (3)	0.000 (3)	0.0044 (17)	0.018 (3)
C15	0.052 (2)	0.054 (4)	0.042 (2)	0.001 (2)	0.0015 (16)	0.0057 (17)
C16	0.0368 (8)	0.0527 (10)	0.0443 (9)	0.000	0.0006 (7)	0.000
C17	0.0403 (9)	0.0692 (12)	0.0410 (9)	0.000	−0.0007 (7)	0.000
C18	0.0354 (8)	0.0670 (12)	0.0509 (10)	0.000	−0.0041 (7)	0.000
C19	0.0372 (9)	0.0658 (11)	0.0511 (10)	0.000	0.0054 (7)	0.000
C20	0.0457 (10)	0.0942 (15)	0.0406 (9)	0.000	0.0006 (8)	0.000
C21	0.0383 (9)	0.0804 (13)	0.0432 (9)	0.000	−0.0042 (7)	0.000

Geometric parameters (Å, º)

O1—N3	1.233 (3)	C8—C9	1.448 (2)
O2—N3	1.225 (3)	C8—H8	0.9300
O3—N4	1.222 (2)	C9—C10	1.504 (3)
O4—N4	1.224 (3)	C10—C15	1.376 (8)
N1—C9	1.296 (2)	C10—C11	1.377 (8)
N1—N2	1.377 (2)	C11—C12	1.388 (8)
N2—C16	1.353 (2)	C11—H11	0.9300
N2—H2N	0.8600	C12—C13	1.364 (7)
N3—C17	1.449 (3)	C12—H12	0.9300
N4—C19	1.453 (2)	C13—C14	1.372 (7)
C1—C2	1.376 (3)	C13—H13	0.9300
C1—C6	1.394 (2)	C14—C15	1.381 (7)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.364 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C21	1.409 (2)
C3—C4	1.371 (3)	C16—C17	1.416 (2)
C3—H3	0.9300	C17—C18	1.382 (2)
C4—C5	1.382 (3)	C18—C19	1.359 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.386 (3)	C19—C20	1.392 (3)
C5—H5	0.9300	C20—C21	1.364 (2)
C6—C7	1.463 (2)	C20—H20	0.9300
C7—C8	1.333 (2)	C21—H21	0.9300
C7—H7	0.9300
C9—N1—N2	114.7 (1)	C15—C10—C11	119.5 (3)
C16—N2—N1	121.5 (1)	C15—C10—C9	121 (1)
C16—N2—H2N	119.3	C11—C10—C9	119 (1)
N1—N2—H2N	119.3	C10—C11—C12	120.2 (5)
O2—N3—O1	122.6 (2)	C10—C11—H11	119.9
O2—N3—C17	119.1 (2)	C12—C11—H11	119.9
O1—N3—C17	118.4 (2)	C13—C12—C11	119.8 (5)
O3—N4—O4	123.4 (2)	C13—C12—H12	120.1
O3—N4—C19	118.5 (2)	C11—C12—H12	120.1
O4—N4—C19	118.0 (2)	C12—C13—C14	120.4 (3)
C2—C1—C6	121.3 (2)	C12—C13—H13	119.8
C2—C1—H1	119.4	C14—C13—H13	119.8
C6—C1—H1	119.4	C13—C14—C15	120.0 (5)
C3—C2—C1	120.1 (2)	C13—C14—H14	120.0
C3—C2—H2	119.9	C15—C14—H14	120.0
C1—C2—H2	119.9	C10—C15—C14	120.1 (5)
C2—C3—C4	119.6 (2)	C10—C15—H15	119.9
C2—C3—H3	120.2	C14—C15—H15	119.9
C4—C3—H3	120.2	N2—C16—C21	121.0 (2)
C3—C4—C5	121.0 (2)	N2—C16—C17	122.4 (2)
C3—C4—H4	119.5	C21—C16—C17	116.6 (2)
C5—C4—H4	119.5	C18—C17—C16	121.9 (2)
C4—C5—C6	120.2 (2)	C18—C17—N3	116.2 (2)
C4—C5—H5	119.9	C16—C17—N3	121.9 (2)
C6—C5—H5	119.9	C19—C18—C17	119.1 (2)
C5—C6—C1	117.8 (2)	C19—C18—H18	120.5
C5—C6—C7	125.0 (2)	C17—C18—H18	120.5
C1—C6—C7	117.2 (2)	C18—C19—C20	121.2 (2)
C8—C7—C6	130.1 (2)	C18—C19—N4	119.1 (2)
C8—C7—H7	115.0	C20—C19—N4	119.7 (2)
C6—C7—H7	115.0	C21—C20—C19	120.0 (2)
C7—C8—C9	122.4 (2)	C21—C20—H20	120.0
C7—C8—H8	118.8	C19—C20—H20	120.0
C9—C8—H8	118.8	C20—C21—C16	121.3 (2)
N1—C9—C8	118.3 (2)	C20—C21—H21	119.4
N1—C9—C10	122.9 (2)	C16—C21—H21	119.4
C8—C9—C10	118.6 (1)
C9—N1—N2—C16	180.0	C9—C10—C15—C14	177.5 (2)
C6—C1—C2—C3	0.0	C13—C14—C15—C10	0.7 (5)
C1—C2—C3—C4	0.0	N1—N2—C16—C21	0.0
C2—C3—C4—C5	0.0	N1—N2—C16—C17	180.0
C3—C4—C5—C6	0.0	N2—C16—C17—C18	180.0
C4—C5—C6—C1	0.0	C21—C16—C17—C18	0.0
C4—C5—C6—C7	180.0	N2—C16—C17—N3	−2.6 (5)
C2—C1—C6—C5	0.0	C21—C16—C17—N3	177.4 (5)
C2—C1—C6—C7	180.0	O2—N3—C17—C18	9.8 (8)
C5—C6—C7—C8	0.0	O1—N3—C17—C18	−170.3 (8)
C1—C6—C7—C8	180.0	O2—N3—C17—C16	−167.8 (6)
C6—C7—C8—C9	180.0	O1—N3—C17—C16	12.2 (6)
N2—N1—C9—C8	180.0	C16—C17—C18—C19	0.0
N2—N1—C9—C10	5.4 (7)	N3—C17—C18—C19	−177.6 (4)
C7—C8—C9—N1	180.0	C17—C18—C19—C20	0.0
C7—C8—C9—C10	−5.1 (7)	C17—C18—C19—N4	180.0
N1—C9—C10—C15	87.4 (6)	O3—N4—C19—C18	2.4 (15)
C8—C9—C10—C15	−87.2 (6)	O4—N4—C19—C18	−174.2 (14)
N1—C9—C10—C11	−93.8 (6)	O3—N4—C19—C20	−177.6 (15)
C8—C9—C10—C11	91.6 (6)	O4—N4—C19—C20	5.8 (14)
C15—C10—C11—C12	0.69 (18)	C18—C19—C20—C21	0.0
C9—C10—C11—C12	−178.14 (18)	N4—C19—C20—C21	180.0
C10—C11—C12—C13	0.5 (2)	C19—C20—C21—C16	0.0
C11—C12—C13—C14	−1.1 (4)	N2—C16—C21—C20	180.0
C12—C13—C14—C15	0.5 (5)	C17—C16—C21—C20	0.0
C11—C10—C15—C14	−1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.86	1.95	2.591 (2)	130