(E)-1-(2,4-Dinitro­phen­yl)-2-{2-[2-(2-nitro­phen­oxy)eth­oxy]benzyl­idene}hydrazine

The molecule of the title compound, C₂₁H₁₇N₅O₈, is non-planar. The central benzene ring makes dihedral angles of 39.57 (10) and 2.93 (17)° with the two terminal benzene rings. An intra­molecular N—H...O hydrogen bond helps to establish the mol­ecular conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.158
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.60 Deg.
              O2   -N1   -O2'     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-1-(2,4-Dinitrophenyl)-2-{2-[2-(2-nitrophenoxy)ethoxy]benzylidene}hydrazine

Crystal data

C21H17N5O8	Z = 2
Mr = 467.40	F(000) = 484
Triclinic, P1	Dx = 1.473 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.953 (3) Å	Cell parameters from 1432 reflections
b = 11.686 (5) Å	θ = 1.8–25.0°
c = 12.524 (5) Å	µ = 0.12 mm^−1
α = 65.107 (6)°	T = 294 K
β = 87.463 (7)°	Block, red
γ = 86.980 (8)°	0.24 × 0.16 × 0.12 mm
V = 1054.0 (7) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3677 independent reflections
Radiation source: fine-focus sealed tube	2069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.961, Tmax = 0.986	k = −13→11
5343 measured reflections	l = −14→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.3108P] where P = (Fo^2 + 2Fc^2)/3
3677 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.39 e Å^−3
33 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6600 (5)	0.0907 (3)	0.2036 (3)	0.1134 (11)
O2	0.8789 (11)	0.1805 (8)	0.1616 (7)	0.117 (3)	0.50
O2'	0.9310 (9)	0.1084 (8)	0.1917 (7)	0.101 (2)	0.50
O3	0.7379 (3)	−0.1064 (2)	0.42224 (18)	0.0661 (7)
O4	0.5633 (3)	−0.2690 (2)	0.37195 (19)	0.0672 (7)
O5	0.3088 (4)	0.2530 (2)	0.1409 (2)	0.0812 (8)
O6	0.1713 (4)	0.4261 (3)	0.0491 (3)	0.1159 (12)
O7	−0.0731 (3)	0.5287 (2)	−0.3156 (2)	0.0808 (8)
O8	−0.1247 (3)	0.3837 (2)	−0.3715 (2)	0.0722 (7)
N1	0.7912 (5)	0.1163 (3)	0.2371 (3)	0.0763 (9)
N2	0.3211 (3)	−0.0528 (2)	0.0871 (2)	0.0484 (6)
N3	0.2968 (3)	0.0684 (2)	0.0760 (2)	0.0498 (6)
H3	0.3425	0.0912	0.1246	0.060*
N4	0.2174 (4)	0.3212 (3)	0.0606 (3)	0.0660 (8)
N5	−0.0666 (3)	0.4192 (3)	−0.3023 (2)	0.0545 (7)
C1	0.7967 (4)	0.1063 (3)	0.3564 (3)	0.0556 (8)
C2	0.8389 (4)	0.2107 (3)	0.3720 (3)	0.0681 (10)
H2	0.8668	0.2846	0.3074	0.082*
C3	0.8396 (5)	0.2050 (4)	0.4824 (4)	0.0834 (12)
H3A	0.8661	0.2751	0.4946	0.100*
C4	0.8001 (5)	0.0928 (5)	0.5766 (4)	0.0867 (13)
H4	0.7991	0.0891	0.6523	0.104*
C5	0.7622 (5)	−0.0134 (4)	0.5620 (3)	0.0727 (10)
H5	0.7366	−0.0876	0.6269	0.087*
C6	0.7626 (4)	−0.0082 (3)	0.4489 (3)	0.0573 (8)
C7	0.6896 (4)	−0.2238 (3)	0.5138 (3)	0.0603 (9)
H7A	0.5793	−0.2145	0.5462	0.072*
H7B	0.7700	−0.2525	0.5767	0.072*
C8	0.6859 (4)	−0.3159 (3)	0.4603 (3)	0.0564 (9)
H8A	0.7955	−0.3237	0.4262	0.068*
H8B	0.6563	−0.3983	0.5196	0.068*
C9	0.5405 (4)	−0.3279 (3)	0.3004 (3)	0.0514 (8)
C10	0.5882 (4)	−0.4519 (3)	0.3272 (3)	0.0629 (9)
H10	0.6476	−0.5002	0.3948	0.075*
C11	0.5453 (5)	−0.5024 (3)	0.2509 (4)	0.0734 (11)
H11	0.5766	−0.5860	0.2681	0.088*
C12	0.4578 (5)	−0.4330 (3)	0.1499 (4)	0.0709 (10)
H12	0.4278	−0.4699	0.1010	0.085*
C13	0.4150 (4)	−0.3079 (3)	0.1224 (3)	0.0585 (9)
H13	0.3580	−0.2598	0.0536	0.070*
C14	0.4565 (4)	−0.2532 (3)	0.1966 (3)	0.0469 (7)
C15	0.4173 (4)	−0.1222 (3)	0.1706 (3)	0.0477 (7)
H15	0.4638	−0.0871	0.2163	0.057*
C16	0.2014 (4)	0.1521 (3)	−0.0108 (2)	0.0422 (7)
C17	0.1633 (4)	0.2767 (3)	−0.0237 (3)	0.0449 (7)
C18	0.0735 (4)	0.3624 (3)	−0.1172 (3)	0.0484 (8)
H18	0.0512	0.4442	−0.1242	0.058*
C19	0.0175 (4)	0.3263 (3)	−0.1993 (2)	0.0451 (7)
C20	0.0455 (4)	0.2032 (3)	−0.1877 (3)	0.0478 (8)
H20	0.0030	0.1786	−0.2426	0.057*
C21	0.1353 (4)	0.1187 (3)	−0.0958 (2)	0.0462 (7)
H21	0.1536	0.0366	−0.0889	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.128 (3)	0.125 (2)	0.080 (2)	−0.001 (2)	−0.0252 (19)	−0.0345 (18)
O2	0.123 (5)	0.125 (5)	0.087 (4)	−0.042 (4)	0.016 (4)	−0.026 (3)
O2'	0.103 (4)	0.130 (4)	0.078 (4)	−0.010 (3)	0.019 (3)	−0.053 (3)
O3	0.0930 (18)	0.0537 (14)	0.0422 (12)	−0.0086 (12)	0.0044 (12)	−0.0108 (11)
O4	0.0711 (16)	0.0644 (14)	0.0612 (15)	0.0236 (12)	−0.0235 (13)	−0.0225 (12)
O5	0.105 (2)	0.0762 (17)	0.0722 (16)	0.0197 (15)	−0.0387 (16)	−0.0396 (14)
O6	0.141 (3)	0.101 (2)	0.148 (3)	0.058 (2)	−0.078 (2)	−0.094 (2)
O7	0.0975 (19)	0.0527 (15)	0.0776 (17)	0.0119 (13)	−0.0249 (14)	−0.0125 (13)
O8	0.0818 (18)	0.0790 (16)	0.0544 (14)	0.0098 (13)	−0.0234 (13)	−0.0261 (13)
N1	0.096 (3)	0.064 (2)	0.061 (2)	−0.0149 (19)	0.006 (2)	−0.0170 (17)
N2	0.0493 (15)	0.0442 (15)	0.0463 (15)	−0.0003 (12)	−0.0021 (13)	−0.0137 (12)
N3	0.0562 (17)	0.0454 (15)	0.0462 (15)	0.0053 (12)	−0.0111 (13)	−0.0177 (12)
N4	0.071 (2)	0.0663 (19)	0.072 (2)	0.0160 (15)	−0.0204 (17)	−0.0403 (17)
N5	0.0511 (17)	0.0508 (17)	0.0488 (16)	0.0053 (13)	−0.0038 (13)	−0.0091 (14)
C1	0.060 (2)	0.056 (2)	0.050 (2)	0.0087 (16)	−0.0018 (16)	−0.0223 (17)
C2	0.069 (2)	0.064 (2)	0.077 (3)	0.0062 (18)	−0.007 (2)	−0.035 (2)
C3	0.073 (3)	0.092 (3)	0.108 (4)	0.014 (2)	−0.015 (3)	−0.065 (3)
C4	0.081 (3)	0.128 (4)	0.077 (3)	0.009 (3)	−0.003 (2)	−0.069 (3)
C5	0.074 (3)	0.093 (3)	0.051 (2)	0.002 (2)	0.0009 (18)	−0.030 (2)
C6	0.057 (2)	0.064 (2)	0.052 (2)	0.0034 (16)	0.0015 (16)	−0.0264 (18)
C7	0.063 (2)	0.058 (2)	0.0382 (17)	−0.0001 (17)	−0.0043 (15)	0.0004 (16)
C8	0.0486 (19)	0.0510 (19)	0.0462 (18)	0.0012 (15)	−0.0071 (15)	0.0028 (15)
C9	0.0443 (19)	0.0463 (18)	0.054 (2)	0.0003 (14)	0.0013 (15)	−0.0119 (16)
C10	0.050 (2)	0.0462 (19)	0.073 (2)	0.0010 (15)	0.0017 (18)	−0.0071 (18)
C11	0.062 (2)	0.045 (2)	0.103 (3)	−0.0047 (17)	0.009 (2)	−0.022 (2)
C12	0.068 (2)	0.062 (2)	0.089 (3)	−0.0113 (19)	0.006 (2)	−0.037 (2)
C13	0.049 (2)	0.058 (2)	0.063 (2)	−0.0054 (16)	0.0011 (17)	−0.0205 (18)
C14	0.0375 (17)	0.0475 (18)	0.0492 (18)	−0.0039 (13)	0.0035 (14)	−0.0142 (15)
C15	0.0457 (18)	0.0480 (18)	0.0436 (17)	0.0017 (14)	−0.0052 (15)	−0.0135 (15)
C16	0.0379 (16)	0.0444 (17)	0.0391 (16)	−0.0005 (13)	−0.0005 (13)	−0.0128 (14)
C17	0.0411 (17)	0.0492 (18)	0.0464 (17)	0.0000 (14)	−0.0038 (14)	−0.0219 (15)
C18	0.0443 (18)	0.0452 (17)	0.0544 (19)	0.0023 (14)	0.0001 (15)	−0.0201 (15)
C19	0.0384 (17)	0.0478 (18)	0.0423 (17)	−0.0015 (13)	0.0004 (14)	−0.0125 (15)
C20	0.0459 (18)	0.0507 (18)	0.0456 (18)	−0.0066 (14)	−0.0025 (15)	−0.0183 (15)
C21	0.0460 (18)	0.0449 (17)	0.0458 (17)	−0.0028 (14)	−0.0009 (15)	−0.0169 (15)

Geometric parameters (Å, º)

O1—N1	1.237 (4)	C5—H5	0.9300
O2—N1	1.159 (6)	C7—C8	1.490 (5)
O2'—N1	1.243 (6)	C7—H7A	0.9700
O3—C6	1.348 (4)	C7—H7B	0.9700
O3—C7	1.427 (4)	C8—H8A	0.9700
O4—C9	1.363 (4)	C8—H8B	0.9700
O4—C8	1.416 (4)	C9—C10	1.379 (4)
O5—N4	1.226 (3)	C9—C14	1.399 (4)
O6—N4	1.211 (3)	C10—C11	1.378 (5)
O7—N5	1.218 (3)	C10—H10	0.9300
O8—N5	1.222 (3)	C11—C12	1.377 (5)
N1—C1	1.450 (4)	C11—H11	0.9300
N2—C15	1.275 (3)	C12—C13	1.380 (5)
N2—N3	1.367 (3)	C12—H12	0.9300
N3—C16	1.347 (3)	C13—C14	1.388 (4)
N3—H3	0.8600	C13—H13	0.9300
N4—C17	1.447 (4)	C14—C15	1.445 (4)
N5—C19	1.452 (4)	C15—H15	0.9300
C1—C2	1.375 (5)	C16—C21	1.408 (4)
C1—C6	1.383 (4)	C16—C17	1.414 (4)
C2—C3	1.356 (5)	C17—C18	1.377 (4)
C2—H2	0.9300	C18—C19	1.365 (4)
C3—C4	1.385 (6)	C18—H18	0.9300
C3—H3A	0.9300	C19—C20	1.390 (4)
C4—C5	1.379 (6)	C20—C21	1.361 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.392 (5)	C21—H21	0.9300
C6—O3—C7	119.2 (3)	C7—C8—H8A	110.4
C9—O4—C8	120.6 (2)	O4—C8—H8B	110.4
O2—N1—O1	114.3 (6)	C7—C8—H8B	110.4
O2—N1—O2'	41.6 (5)	H8A—C8—H8B	108.6
O1—N1—O2'	121.9 (5)	O4—C9—C10	124.4 (3)
O2—N1—C1	122.8 (5)	O4—C9—C14	114.3 (3)
O1—N1—C1	119.0 (4)	C10—C9—C14	121.3 (3)
O2'—N1—C1	114.7 (5)	C11—C10—C9	118.2 (3)
C15—N2—N3	114.4 (3)	C11—C10—H10	120.9
C16—N3—N2	120.2 (2)	C9—C10—H10	120.9
C16—N3—H3	119.9	C12—C11—C10	122.1 (3)
N2—N3—H3	119.9	C12—C11—H11	118.9
O6—N4—O5	121.6 (3)	C10—C11—H11	118.9
O6—N4—C17	118.6 (3)	C11—C12—C13	119.1 (4)
O5—N4—C17	119.8 (3)	C11—C12—H12	120.5
O7—N5—O8	123.6 (3)	C13—C12—H12	120.5
O7—N5—C19	117.9 (3)	C12—C13—C14	120.6 (3)
O8—N5—C19	118.4 (3)	C12—C13—H13	119.7
C2—C1—C6	123.1 (3)	C14—C13—H13	119.7
C2—C1—N1	118.2 (3)	C13—C14—C9	118.7 (3)
C6—C1—N1	118.6 (3)	C13—C14—C15	122.7 (3)
C3—C2—C1	119.4 (4)	C9—C14—C15	118.7 (3)
C3—C2—H2	120.3	N2—C15—C14	122.4 (3)
C1—C2—H2	120.3	N2—C15—H15	118.8
C2—C3—C4	118.8 (4)	C14—C15—H15	118.8
C2—C3—H3A	120.6	N3—C16—C21	120.5 (3)
C4—C3—H3A	120.6	N3—C16—C17	123.2 (3)
C5—C4—C3	122.2 (4)	C21—C16—C17	116.2 (3)
C5—C4—H4	118.9	C18—C17—C16	121.9 (3)
C3—C4—H4	118.9	C18—C17—N4	116.4 (3)
C4—C5—C6	119.2 (4)	C16—C17—N4	121.7 (3)
C4—C5—H5	120.4	C19—C18—C17	119.4 (3)
C6—C5—H5	120.4	C19—C18—H18	120.3
O3—C6—C1	117.2 (3)	C17—C18—H18	120.3
O3—C6—C5	125.5 (3)	C18—C19—C20	120.8 (3)
C1—C6—C5	117.2 (3)	C18—C19—N5	119.3 (3)
O3—C7—C8	107.0 (3)	C20—C19—N5	119.8 (3)
O3—C7—H7A	110.3	C21—C20—C19	119.8 (3)
C8—C7—H7A	110.3	C21—C20—H20	120.1
O3—C7—H7B	110.3	C19—C20—H20	120.1
C8—C7—H7B	110.3	C20—C21—C16	121.8 (3)
H7A—C7—H7B	108.6	C20—C21—H21	119.1
O4—C8—C7	106.9 (2)	C16—C21—H21	119.1
O4—C8—H8A	110.4
C15—N2—N3—C16	178.2 (3)	C12—C13—C14—C15	178.8 (3)
O2—N1—C1—C2	32.2 (8)	O4—C9—C14—C13	−174.8 (3)
O1—N1—C1—C2	−124.2 (4)	C10—C9—C14—C13	2.7 (4)
O2'—N1—C1—C2	79.1 (6)	O4—C9—C14—C15	5.5 (4)
O2—N1—C1—C6	−146.6 (7)	C10—C9—C14—C15	−176.9 (3)
O1—N1—C1—C6	57.1 (5)	N3—N2—C15—C14	179.4 (3)
O2'—N1—C1—C6	−99.7 (6)	C13—C14—C15—N2	10.4 (5)
C6—C1—C2—C3	−3.4 (5)	C9—C14—C15—N2	−169.9 (3)
N1—C1—C2—C3	177.8 (3)	N2—N3—C16—C21	−4.3 (4)
C1—C2—C3—C4	1.0 (6)	N2—N3—C16—C17	176.4 (3)
C2—C3—C4—C5	0.8 (6)	N3—C16—C17—C18	176.2 (3)
C3—C4—C5—C6	−0.3 (6)	C21—C16—C17—C18	−3.0 (4)
C7—O3—C6—C1	−175.2 (3)	N3—C16—C17—N4	−3.5 (4)
C7—O3—C6—C5	7.1 (5)	C21—C16—C17—N4	177.3 (3)
C2—C1—C6—O3	−174.1 (3)	O6—N4—C17—C18	5.2 (5)
N1—C1—C6—O3	4.7 (5)	O5—N4—C17—C18	−174.4 (3)
C2—C1—C6—C5	3.8 (5)	O6—N4—C17—C16	−175.1 (3)
N1—C1—C6—C5	−177.4 (3)	O5—N4—C17—C16	5.3 (5)
C4—C5—C6—O3	175.8 (3)	C16—C17—C18—C19	0.8 (4)
C4—C5—C6—C1	−1.9 (5)	N4—C17—C18—C19	−179.4 (3)
C6—O3—C7—C8	−175.4 (3)	C17—C18—C19—C20	2.0 (4)
C9—O4—C8—C7	174.6 (3)	C17—C18—C19—N5	−175.6 (3)
O3—C7—C8—O4	−61.4 (3)	O7—N5—C19—C18	5.2 (4)
C8—O4—C9—C10	21.3 (4)	O8—N5—C19—C18	−175.8 (3)
C8—O4—C9—C14	−161.2 (3)	O7—N5—C19—C20	−172.4 (3)
O4—C9—C10—C11	174.9 (3)	O8—N5—C19—C20	6.6 (4)
C14—C9—C10—C11	−2.4 (5)	C18—C19—C20—C21	−2.5 (4)
C9—C10—C11—C12	0.2 (5)	N5—C19—C20—C21	175.1 (3)
C10—C11—C12—C13	1.7 (5)	C19—C20—C21—C16	0.1 (4)
C11—C12—C13—C14	−1.3 (5)	N3—C16—C21—C20	−176.8 (3)
C12—C13—C14—C9	−0.8 (5)	C17—C16—C21—C20	2.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5	0.86	1.99	2.614 (3)	129