(E)-1-(2,4-Dinitro­phen­yl)-2-[3-meth­oxy-2-(p-tolyl­sulfon­yloxy)benzyl­idene]hydrazine

In the title compound, C₂₁H₁₈N₄O₈S, the o-vanillin group makes dihedral angles of 73.80 (6) and 6.46 (8)° with the terminal 4-methyl­benzene ring and the phenyl­hydrazine mean plane, respectively. An intra­molecular hydrogen bond links the NH group to an O atom of the nearest nitro group. The crystal structure contains four weak inter­molecular hydrogen bonds, namely one N—H...O and three C—H...O.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.113
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O8     -   N4      ..       5.64 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C17     ..       5.30 su
PLAT430_ALERT_2_C Short Inter D...A Contact  O5     ..  O7      ..       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O6      ..       2.70 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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-[3-methoxy-2-(p- tolylsulfonyloxy)benzylidene]hydrazine

Crystal data

C21H18N4O8S	F(000) = 1008
Mr = 486.46	Dx = 1.499 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2718 reflections
a = 7.9826 (14) Å	θ = 2.5–24.0°
b = 16.545 (3) Å	µ = 0.21 mm^−1
c = 16.664 (3) Å	T = 294 K
β = 101.556 (3)°	Block, yellow
V = 2156.2 (7) Å^3	0.30 × 0.26 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4410 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.921, Tmax = 0.956	k = −20→11
12063 measured reflections	l = −20→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.2099P] where P = (Fo^2 + 2Fc^2)/3
4410 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.29 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 > 2σ(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
S1	0.17927 (9)	0.96056 (4)	0.25866 (4)	0.03874 (19)
O1	0.3135 (2)	0.92729 (11)	0.31819 (11)	0.0574 (5)
O2	0.0987 (3)	0.91330 (10)	0.19071 (10)	0.0568 (5)
O3	0.2701 (2)	1.03677 (9)	0.22593 (9)	0.0343 (4)
O4	0.1060 (3)	1.17250 (10)	0.23823 (11)	0.0564 (5)
O5	0.6339 (2)	0.75882 (11)	0.06700 (10)	0.0572 (5)
O6	0.6991 (3)	0.66444 (12)	−0.00969 (11)	0.0679 (6)
O7	0.5297 (2)	0.66410 (11)	−0.29569 (10)	0.0513 (5)
O8	0.3287 (3)	0.74508 (12)	−0.35406 (11)	0.0612 (6)
N1	0.3256 (2)	0.94495 (11)	0.00256 (11)	0.0349 (5)
N2	0.4259 (2)	0.87742 (11)	0.00404 (11)	0.0345 (5)
H2	0.4822	0.8590	0.0498	0.041*
N3	0.6267 (3)	0.72778 (12)	−0.00040 (12)	0.0403 (5)
N4	0.4327 (3)	0.72184 (13)	−0.29403 (13)	0.0429 (5)
C1	0.0226 (3)	0.99871 (13)	0.30845 (13)	0.0333 (5)
C2	0.0700 (3)	1.05060 (15)	0.37441 (15)	0.0443 (6)
H2A	0.1813	1.0701	0.3885	0.053*
C3	−0.0512 (4)	1.07283 (16)	0.41875 (15)	0.0523 (7)
H3	−0.0210	1.1083	0.4626	0.063*
C4	−0.2176 (4)	1.04328 (16)	0.39920 (17)	0.0506 (7)
C5	−0.2599 (4)	0.99230 (16)	0.33251 (19)	0.0531 (7)
H5	−0.3708	0.9724	0.3183	0.064*
C6	−0.1423 (3)	0.97043 (14)	0.28690 (16)	0.0430 (6)
H6	−0.1737	0.9367	0.2417	0.052*
C7	−0.3476 (4)	1.0690 (2)	0.4483 (2)	0.0865 (11)
H7A	−0.4418	1.0318	0.4390	0.130*
H7B	−0.3882	1.1223	0.4318	0.130*
H7C	−0.2956	1.0694	0.5055	0.130*
C8	0.1902 (3)	1.07608 (13)	0.15258 (13)	0.0317 (5)
C9	0.2106 (3)	1.04610 (13)	0.07704 (13)	0.0321 (5)
C10	0.1328 (3)	1.08864 (14)	0.00719 (14)	0.0389 (6)
H10	0.1415	1.0697	−0.0443	0.047*
C11	0.0435 (3)	1.15842 (15)	0.01413 (16)	0.0446 (6)
H11	−0.0107	1.1851	−0.0331	0.054*
C12	0.0326 (3)	1.18967 (15)	0.08976 (16)	0.0464 (7)
H12	−0.0246	1.2381	0.0932	0.056*
C13	0.1069 (3)	1.14866 (14)	0.16042 (15)	0.0385 (6)
C14	0.0538 (4)	1.25298 (16)	0.25150 (19)	0.0618 (8)
H14A	0.1266	1.2906	0.2310	0.093*
H14B	0.0620	1.2618	0.3091	0.093*
H14C	−0.0623	1.2608	0.2234	0.093*
C15	0.3146 (3)	0.97408 (13)	0.07198 (14)	0.0342 (6)
H15	0.3729	0.9495	0.1197	0.041*
C16	0.4357 (3)	0.83999 (13)	−0.06728 (13)	0.0302 (5)
C17	0.5290 (3)	0.76803 (13)	−0.07215 (13)	0.0302 (5)
C18	0.5304 (3)	0.73063 (13)	−0.14649 (13)	0.0332 (5)
H18	0.5920	0.6832	−0.1484	0.040*
C19	0.4406 (3)	0.76408 (13)	−0.21662 (13)	0.0332 (6)
C20	0.3499 (3)	0.83540 (14)	−0.21536 (14)	0.0393 (6)
H20	0.2896	0.8575	−0.2639	0.047*
C21	0.3498 (3)	0.87293 (14)	−0.14240 (13)	0.0377 (6)
H21	0.2914	0.9215	−0.1422	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0527 (4)	0.0302 (3)	0.0376 (4)	0.0025 (3)	0.0193 (3)	0.0014 (3)
O1	0.0612 (13)	0.0599 (12)	0.0569 (11)	0.0265 (10)	0.0261 (10)	0.0238 (9)
O2	0.0918 (15)	0.0362 (10)	0.0498 (11)	−0.0217 (10)	0.0320 (10)	−0.0160 (8)
O3	0.0414 (10)	0.0303 (9)	0.0330 (9)	−0.0008 (7)	0.0117 (7)	−0.0020 (7)
O4	0.0888 (15)	0.0347 (10)	0.0525 (11)	0.0108 (10)	0.0302 (10)	−0.0090 (8)
O5	0.0748 (14)	0.0685 (13)	0.0277 (9)	0.0197 (10)	0.0089 (9)	0.0023 (9)
O6	0.0937 (17)	0.0536 (12)	0.0549 (12)	0.0403 (12)	0.0111 (11)	0.0084 (9)
O7	0.0681 (13)	0.0435 (11)	0.0476 (11)	0.0034 (10)	0.0242 (10)	−0.0103 (8)
O8	0.0748 (14)	0.0730 (14)	0.0320 (10)	0.0093 (11)	0.0014 (10)	−0.0099 (9)
N1	0.0413 (12)	0.0316 (11)	0.0339 (11)	0.0003 (9)	0.0129 (9)	−0.0028 (8)
N2	0.0437 (12)	0.0342 (11)	0.0257 (10)	0.0053 (9)	0.0074 (9)	0.0011 (8)
N3	0.0451 (13)	0.0419 (13)	0.0359 (12)	0.0045 (10)	0.0132 (10)	0.0061 (10)
N4	0.0530 (15)	0.0427 (13)	0.0371 (13)	−0.0085 (11)	0.0189 (11)	−0.0068 (10)
C1	0.0375 (14)	0.0314 (13)	0.0324 (13)	0.0003 (11)	0.0106 (11)	0.0046 (10)
C2	0.0399 (15)	0.0543 (17)	0.0405 (14)	−0.0038 (12)	0.0128 (12)	−0.0067 (12)
C3	0.059 (2)	0.0604 (18)	0.0408 (15)	0.0069 (15)	0.0193 (14)	−0.0033 (13)
C4	0.0477 (18)	0.0508 (17)	0.0610 (18)	0.0134 (14)	0.0294 (15)	0.0226 (15)
C5	0.0374 (16)	0.0448 (16)	0.079 (2)	−0.0020 (13)	0.0161 (15)	0.0159 (15)
C6	0.0420 (16)	0.0338 (14)	0.0519 (16)	−0.0016 (12)	0.0061 (13)	0.0046 (11)
C7	0.078 (3)	0.097 (3)	0.102 (3)	0.022 (2)	0.062 (2)	0.031 (2)
C8	0.0339 (14)	0.0274 (12)	0.0362 (13)	−0.0040 (10)	0.0126 (11)	0.0011 (10)
C9	0.0344 (14)	0.0296 (13)	0.0343 (13)	−0.0060 (10)	0.0116 (11)	−0.0006 (10)
C10	0.0429 (15)	0.0396 (14)	0.0349 (13)	−0.0030 (12)	0.0091 (12)	0.0004 (11)
C11	0.0438 (16)	0.0416 (15)	0.0469 (16)	0.0018 (13)	0.0055 (13)	0.0119 (12)
C12	0.0465 (17)	0.0310 (14)	0.0651 (19)	0.0033 (12)	0.0200 (14)	0.0040 (13)
C13	0.0416 (15)	0.0312 (14)	0.0464 (15)	−0.0007 (11)	0.0174 (12)	−0.0012 (11)
C14	0.069 (2)	0.0384 (16)	0.082 (2)	0.0049 (14)	0.0242 (17)	−0.0249 (15)
C15	0.0416 (15)	0.0325 (13)	0.0300 (13)	−0.0019 (11)	0.0105 (11)	0.0009 (10)
C16	0.0346 (14)	0.0304 (13)	0.0276 (12)	−0.0040 (10)	0.0109 (10)	−0.0006 (10)
C17	0.0343 (14)	0.0303 (13)	0.0268 (12)	−0.0006 (10)	0.0078 (10)	0.0053 (10)
C18	0.0355 (14)	0.0284 (13)	0.0390 (14)	−0.0013 (10)	0.0152 (11)	−0.0002 (11)
C19	0.0408 (15)	0.0323 (14)	0.0283 (12)	−0.0046 (11)	0.0116 (11)	−0.0053 (10)
C20	0.0485 (16)	0.0394 (14)	0.0294 (13)	0.0009 (12)	0.0062 (11)	0.0027 (11)
C21	0.0493 (16)	0.0330 (14)	0.0315 (13)	0.0055 (11)	0.0099 (12)	0.0018 (10)

Geometric parameters (Å, º)

S1—O1	1.4176 (18)	C6—H6	0.9300
S1—O2	1.4197 (17)	C7—H7A	0.9600
S1—O3	1.6035 (16)	C7—H7B	0.9600
S1—C1	1.751 (2)	C7—H7C	0.9600
O3—C8	1.418 (3)	C8—C13	1.392 (3)
O4—C13	1.357 (3)	C8—C9	1.392 (3)
O4—C14	1.426 (3)	C9—C10	1.395 (3)
O5—N3	1.226 (2)	C9—C15	1.465 (3)
O6—N3	1.221 (2)	C10—C11	1.374 (3)
O7—N4	1.234 (3)	C10—H10	0.9300
O8—N4	1.227 (3)	C11—C12	1.381 (3)
N1—C15	1.272 (3)	C11—H11	0.9300
N1—N2	1.372 (2)	C12—C13	1.385 (3)
N2—C16	1.356 (3)	C12—H12	0.9300
N2—H2	0.8600	C14—H14A	0.9600
N3—C17	1.452 (3)	C14—H14B	0.9600
N4—C19	1.457 (3)	C14—H14C	0.9600
C1—C6	1.375 (3)	C15—H15	0.9300
C1—C2	1.386 (3)	C16—C21	1.411 (3)
C2—C3	1.379 (4)	C16—C17	1.415 (3)
C2—H2A	0.9300	C17—C18	1.387 (3)
C3—C4	1.391 (4)	C18—C19	1.360 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.382 (4)	C19—C20	1.387 (3)
C4—C7	1.507 (4)	C20—C21	1.365 (3)
C5—C6	1.370 (4)	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300
O1—S1—O2	120.17 (12)	C9—C8—O3	120.1 (2)
O1—S1—O3	102.33 (10)	C8—C9—C10	117.5 (2)
O2—S1—O3	108.99 (9)	C8—C9—C15	120.8 (2)
O1—S1—C1	108.65 (11)	C10—C9—C15	121.7 (2)
O2—S1—C1	108.90 (12)	C11—C10—C9	120.4 (2)
O3—S1—C1	106.99 (10)	C11—C10—H10	119.8
C8—O3—S1	119.87 (14)	C9—C10—H10	119.8
C13—O4—C14	118.5 (2)	C10—C11—C12	121.3 (2)
C15—N1—N2	116.00 (19)	C10—C11—H11	119.3
C16—N2—N1	119.48 (18)	C12—C11—H11	119.3
C16—N2—H2	120.3	C11—C12—C13	119.8 (2)
N1—N2—H2	120.3	C11—C12—H12	120.1
O6—N3—O5	122.6 (2)	C13—C12—H12	120.1
O6—N3—C17	118.6 (2)	O4—C13—C12	125.9 (2)
O5—N3—C17	118.8 (2)	O4—C13—C8	115.8 (2)
O8—N4—O7	123.4 (2)	C12—C13—C8	118.3 (2)
O8—N4—C19	118.3 (2)	O4—C14—H14A	109.5
O7—N4—C19	118.3 (2)	O4—C14—H14B	109.5
C6—C1—C2	120.8 (2)	H14A—C14—H14B	109.5
C6—C1—S1	119.38 (19)	O4—C14—H14C	109.5
C2—C1—S1	119.45 (19)	H14A—C14—H14C	109.5
C3—C2—C1	118.7 (2)	H14B—C14—H14C	109.5
C3—C2—H2A	120.6	N1—C15—C9	120.2 (2)
C1—C2—H2A	120.6	N1—C15—H15	119.9
C2—C3—C4	121.3 (3)	C9—C15—H15	119.9
C2—C3—H3	119.3	N2—C16—C21	119.9 (2)
C4—C3—H3	119.3	N2—C16—C17	123.9 (2)
C5—C4—C3	118.1 (2)	C21—C16—C17	116.2 (2)
C5—C4—C7	121.7 (3)	C18—C17—C16	121.7 (2)
C3—C4—C7	120.2 (3)	C18—C17—N3	115.6 (2)
C6—C5—C4	121.6 (3)	C16—C17—N3	122.7 (2)
C6—C5—H5	119.2	C19—C18—C17	119.3 (2)
C4—C5—H5	119.2	C19—C18—H18	120.4
C5—C6—C1	119.5 (3)	C17—C18—H18	120.4
C5—C6—H6	120.3	C18—C19—C20	121.3 (2)
C1—C6—H6	120.3	C18—C19—N4	119.2 (2)
C4—C7—H7A	109.5	C20—C19—N4	119.4 (2)
C4—C7—H7B	109.5	C21—C20—C19	119.6 (2)
H7A—C7—H7B	109.5	C21—C20—H20	120.2
C4—C7—H7C	109.5	C19—C20—H20	120.2
H7A—C7—H7C	109.5	C20—C21—C16	121.8 (2)
H7B—C7—H7C	109.5	C20—C21—H21	119.1
C13—C8—C9	122.5 (2)	C16—C21—H21	119.1
C13—C8—O3	117.1 (2)
O1—S1—O3—C8	165.77 (16)	C11—C12—C13—O4	179.9 (2)
O2—S1—O3—C8	37.52 (19)	C11—C12—C13—C8	−0.4 (4)
C1—S1—O3—C8	−80.08 (17)	C9—C8—C13—O4	−176.2 (2)
C15—N1—N2—C16	176.0 (2)	O3—C8—C13—O4	−2.3 (3)
O1—S1—C1—C6	−122.50 (19)	C9—C8—C13—C12	4.1 (4)
O2—S1—C1—C6	10.0 (2)	O3—C8—C13—C12	177.9 (2)
O3—S1—C1—C6	127.71 (18)	N2—N1—C15—C9	−179.97 (19)
O1—S1—C1—C2	51.0 (2)	C8—C9—C15—N1	176.6 (2)
O2—S1—C1—C2	−176.48 (18)	C10—C9—C15—N1	−5.5 (3)
O3—S1—C1—C2	−58.8 (2)	N1—N2—C16—C21	3.1 (3)
C6—C1—C2—C3	0.7 (4)	N1—N2—C16—C17	−177.0 (2)
S1—C1—C2—C3	−172.72 (19)	N2—C16—C17—C18	177.8 (2)
C1—C2—C3—C4	1.0 (4)	C21—C16—C17—C18	−2.3 (3)
C2—C3—C4—C5	−1.6 (4)	N2—C16—C17—N3	−1.1 (3)
C2—C3—C4—C7	−179.6 (2)	C21—C16—C17—N3	178.8 (2)
C3—C4—C5—C6	0.6 (4)	O6—N3—C17—C18	−1.4 (3)
C7—C4—C5—C6	178.6 (2)	O5—N3—C17—C18	178.3 (2)
C4—C5—C6—C1	1.0 (4)	O6—N3—C17—C16	177.6 (2)
C2—C1—C6—C5	−1.6 (4)	O5—N3—C17—C16	−2.7 (3)
S1—C1—C6—C5	171.75 (18)	C16—C17—C18—C19	0.4 (3)
S1—O3—C8—C13	102.1 (2)	N3—C17—C18—C19	179.4 (2)
S1—O3—C8—C9	−83.9 (2)	C17—C18—C19—C20	1.0 (3)
C13—C8—C9—C10	−4.6 (3)	C17—C18—C19—N4	−175.9 (2)
O3—C8—C9—C10	−178.26 (19)	O8—N4—C19—C18	167.7 (2)
C13—C8—C9—C15	173.4 (2)	O7—N4—C19—C18	−11.7 (3)
O3—C8—C9—C15	−0.2 (3)	O8—N4—C19—C20	−9.2 (3)
C8—C9—C10—C11	1.5 (3)	O7—N4—C19—C20	171.4 (2)
C15—C9—C10—C11	−176.5 (2)	C18—C19—C20—C21	−0.2 (4)
C9—C10—C11—C12	2.1 (4)	N4—C19—C20—C21	176.6 (2)
C10—C11—C12—C13	−2.6 (4)	C19—C20—C21—C16	−1.9 (4)
C14—O4—C13—C12	−12.6 (4)	N2—C16—C21—C20	−177.1 (2)
C14—O4—C13—C8	167.7 (2)	C17—C16—C21—C20	3.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.86	2.04	2.648 (3)	127
C2—H2A···O6^i	0.93	2.58	3.219 (3)	126
C3—H3···O6^i	0.93	2.70	3.284 (4)	122
C15—H15···O7^ii	0.93	2.53	3.394 (3)	155
N2—H2···O7^ii	0.86	2.55	3.345 (2)	153

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+3/2, z+1/2.