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In the title compound, C21H18N4O8S, the isovanillin group makes dihedral angles of 31.69 (9) and 3.67 (9)° with the terminal 4-methyl­benzene ring and the phenyl­hydrazine mean plane, respectively. The crystal structure is stabilized by a bifurcated intra­molecular/inter­molecular N—H...O hydrogen-bond system and a weak non-classical inter­molecular C—H...(O,O) hydrogen-bond contact.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038414/at2120sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038414/at2120Isup2.hkl
Contains datablock I

CCDC reference: 623980

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.131
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N3 .. 6.00 su PLAT430_ALERT_2_C Short Inter D...A Contact O5 .. O5 .. 2.86 Ang.
0 ALERT level A = In general: serious problem 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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-[4-methoxy-3-(4- methylbenzenesulfonyloxy)benzylidene]hydrazine top
Crystal data top
C21H18N4O8SZ = 2
Mr = 486.46F(000) = 504
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.365 (2) ÅCell parameters from 1469 reflections
b = 12.978 (4) Åθ = 2.9–25.4°
c = 13.547 (4) ŵ = 0.20 mm1
α = 62.937 (4)°T = 294 K
β = 88.904 (5)°Block, red
γ = 74.845 (5)°0.28 × 0.24 × 0.20 mm
V = 1105.5 (6) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3876 independent reflections
Radiation source: fine-focus sealed tube2342 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 78
Tmin = 0.928, Tmax = 0.960k = 1511
5658 measured reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0602P)2]
where P = (Fo2 + 2Fc2)/3
3876 reflections(Δ/σ)max = 0.002
309 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
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 > 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 (Å2) top
xyzUiso*/Ueq
S10.32196 (10)0.69704 (7)0.23299 (6)0.0520 (3)
O10.3420 (2)0.70261 (15)0.11219 (15)0.0466 (5)
O20.3439 (3)0.80576 (17)0.22652 (17)0.0653 (6)
O30.1504 (3)0.66588 (18)0.26001 (18)0.0694 (6)
O40.2445 (3)0.93559 (17)0.04086 (16)0.0630 (6)
O51.5851 (3)0.40835 (19)0.10937 (19)0.0710 (7)
O61.7530 (3)0.2221 (2)0.19030 (19)0.0770 (7)
O71.5159 (4)0.0951 (2)0.4343 (2)0.0896 (8)
O81.2291 (4)0.0581 (2)0.4756 (2)0.1047 (9)
N11.0329 (3)0.5365 (2)0.10224 (19)0.0471 (6)
N21.2165 (3)0.46602 (19)0.12128 (19)0.0481 (6)
H21.30380.49650.08700.058*
N31.6019 (3)0.3005 (2)0.1711 (2)0.0559 (6)
N41.3595 (5)0.0262 (3)0.4229 (2)0.0701 (8)
C10.5141 (4)0.5761 (2)0.3192 (2)0.0475 (7)
C20.6868 (4)0.5954 (3)0.3317 (2)0.0606 (8)
H2A0.69980.67310.29670.073*
C30.8384 (4)0.4991 (3)0.3958 (2)0.0673 (9)
H30.95450.51260.40240.081*
C40.8233 (5)0.3831 (3)0.4508 (3)0.0645 (9)
C50.6504 (5)0.3657 (3)0.4374 (3)0.0711 (10)
H50.63730.28800.47380.085*
C60.4962 (4)0.4604 (3)0.3716 (3)0.0642 (9)
H60.38160.44630.36250.077*
C70.9907 (5)0.2780 (3)0.5247 (3)0.0917 (12)
H7A0.99380.27010.59870.138*
H7B1.10600.29250.49480.138*
H7C0.97810.20510.52730.138*
C80.4823 (4)0.7526 (2)0.0511 (2)0.0407 (6)
C90.4301 (4)0.8749 (2)0.0283 (2)0.0448 (7)
C100.5699 (4)0.9215 (2)0.0867 (2)0.0516 (7)
H100.54001.00240.13950.062*
C110.7553 (4)0.8483 (2)0.0671 (2)0.0490 (7)
H110.84850.88160.10530.059*
C120.8029 (4)0.7259 (2)0.0091 (2)0.0408 (6)
C130.6615 (4)0.6792 (2)0.0672 (2)0.0403 (6)
H130.68930.59740.11730.048*
C140.1784 (5)1.0540 (3)0.1338 (3)0.0825 (11)
H14A0.24271.10620.12660.124*
H14B0.04461.08530.13530.124*
H14C0.20381.04980.20190.124*
C150.9963 (4)0.6476 (3)0.0297 (2)0.0457 (7)
H151.09110.67810.00940.055*
C161.2568 (4)0.3473 (2)0.1953 (2)0.0439 (7)
C171.4398 (4)0.2647 (2)0.2218 (2)0.0436 (7)
C181.4713 (4)0.1431 (2)0.2956 (2)0.0499 (7)
H181.59210.09000.31140.060*
C191.3243 (4)0.1021 (2)0.3447 (2)0.0518 (7)
C201.1423 (4)0.1804 (3)0.3228 (2)0.0557 (8)
H201.04360.15150.35810.067*
C211.1106 (4)0.2990 (3)0.2495 (2)0.0526 (8)
H210.98840.35020.23440.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0501 (5)0.0484 (5)0.0525 (5)0.0132 (4)0.0113 (3)0.0201 (4)
O10.0414 (10)0.0499 (12)0.0469 (11)0.0155 (9)0.0049 (8)0.0198 (9)
O20.0848 (15)0.0477 (13)0.0656 (14)0.0164 (11)0.0120 (11)0.0298 (11)
O30.0460 (12)0.0801 (15)0.0746 (15)0.0212 (11)0.0209 (11)0.0286 (12)
O40.0544 (13)0.0470 (12)0.0628 (14)0.0067 (10)0.0050 (10)0.0158 (10)
O50.0505 (13)0.0516 (14)0.0885 (17)0.0181 (11)0.0127 (11)0.0122 (12)
O60.0397 (12)0.0689 (15)0.0951 (18)0.0051 (12)0.0094 (11)0.0211 (13)
O70.0838 (18)0.0551 (15)0.096 (2)0.0074 (14)0.0052 (15)0.0131 (13)
O80.097 (2)0.0728 (17)0.114 (2)0.0419 (15)0.0264 (17)0.0087 (15)
N10.0380 (14)0.0460 (15)0.0542 (15)0.0078 (11)0.0058 (11)0.0230 (12)
N20.0367 (13)0.0459 (15)0.0549 (15)0.0114 (11)0.0073 (11)0.0182 (12)
N30.0405 (15)0.0608 (18)0.0591 (17)0.0124 (14)0.0026 (12)0.0230 (14)
N40.078 (2)0.0586 (19)0.0643 (19)0.0260 (17)0.0041 (16)0.0175 (15)
C10.0497 (17)0.0444 (17)0.0443 (17)0.0157 (14)0.0078 (13)0.0161 (13)
C20.065 (2)0.060 (2)0.0475 (19)0.0270 (17)0.0002 (16)0.0119 (15)
C30.057 (2)0.087 (3)0.049 (2)0.0268 (19)0.0006 (16)0.0209 (19)
C40.068 (2)0.069 (2)0.0459 (19)0.0036 (19)0.0021 (16)0.0265 (17)
C50.087 (3)0.0398 (19)0.071 (2)0.0147 (18)0.006 (2)0.0149 (16)
C60.063 (2)0.054 (2)0.072 (2)0.0234 (18)0.0055 (17)0.0230 (17)
C70.095 (3)0.089 (3)0.058 (2)0.018 (2)0.011 (2)0.029 (2)
C80.0393 (16)0.0398 (16)0.0418 (16)0.0113 (13)0.0036 (12)0.0181 (13)
C90.0491 (17)0.0364 (16)0.0425 (17)0.0042 (14)0.0050 (13)0.0169 (13)
C100.066 (2)0.0359 (16)0.0431 (17)0.0106 (15)0.0005 (15)0.0122 (13)
C110.0609 (19)0.0444 (17)0.0421 (16)0.0241 (15)0.0127 (14)0.0160 (14)
C120.0430 (16)0.0427 (17)0.0403 (16)0.0133 (13)0.0027 (12)0.0216 (13)
C130.0457 (16)0.0323 (15)0.0393 (15)0.0117 (13)0.0016 (12)0.0132 (12)
C140.086 (3)0.053 (2)0.068 (2)0.0200 (18)0.0207 (19)0.0141 (18)
C150.0430 (16)0.0533 (19)0.0442 (17)0.0189 (14)0.0091 (13)0.0228 (15)
C160.0443 (16)0.0474 (18)0.0441 (17)0.0138 (14)0.0054 (13)0.0242 (14)
C170.0365 (15)0.0495 (18)0.0422 (16)0.0131 (14)0.0031 (12)0.0187 (14)
C180.0444 (17)0.0519 (19)0.0482 (18)0.0061 (15)0.0029 (14)0.0227 (15)
C190.0550 (19)0.0483 (18)0.0445 (18)0.0172 (16)0.0021 (14)0.0139 (14)
C200.0540 (19)0.062 (2)0.0492 (19)0.0255 (17)0.0128 (14)0.0202 (16)
C210.0456 (17)0.055 (2)0.0514 (18)0.0119 (15)0.0111 (14)0.0211 (15)
Geometric parameters (Å, º) top
S1—O31.4169 (19)C6—H60.9300
S1—O21.425 (2)C7—H7A0.9600
S1—O11.610 (2)C7—H7B0.9600
S1—C11.750 (3)C7—H7C0.9600
O1—C81.415 (3)C8—C131.365 (3)
O4—C91.357 (3)C8—C91.402 (4)
O4—C141.434 (3)C9—C101.382 (4)
O5—N31.234 (3)C10—C111.394 (4)
O6—N31.233 (3)C10—H100.9300
O7—N41.222 (3)C11—C121.394 (4)
O8—N41.231 (3)C11—H110.9300
N1—C151.279 (3)C12—C131.391 (3)
N1—N21.372 (3)C12—C151.463 (3)
N2—C161.354 (3)C13—H130.9300
N2—H20.8600C14—H14A0.9600
N3—C171.443 (3)C14—H14B0.9600
N4—C191.464 (4)C14—H14C0.9600
C1—C61.381 (4)C15—H150.9300
C1—C21.386 (4)C16—C211.413 (4)
C2—C31.372 (4)C16—C171.417 (3)
C2—H2A0.9300C17—C181.387 (4)
C3—C41.378 (4)C18—C191.359 (4)
C3—H30.9300C18—H180.9300
C4—C51.379 (4)C19—C201.395 (4)
C4—C71.520 (4)C20—C211.356 (4)
C5—C61.381 (4)C20—H200.9300
C5—H50.9300C21—H210.9300
O3—S1—O2120.84 (13)C9—C8—O1118.8 (2)
O3—S1—O1102.66 (12)O4—C9—C10126.4 (2)
O2—S1—O1108.60 (11)O4—C9—C8116.0 (2)
O3—S1—C1110.07 (13)C10—C9—C8117.6 (3)
O2—S1—C1109.17 (13)C9—C10—C11120.6 (3)
O1—S1—C1104.06 (12)C9—C10—H10119.7
C8—O1—S1117.51 (15)C11—C10—H10119.7
C9—O4—C14117.7 (2)C12—C11—C10120.9 (3)
C15—N1—N2117.5 (2)C12—C11—H11119.6
C16—N2—N1118.4 (2)C10—C11—H11119.6
C16—N2—H2120.8C13—C12—C11118.3 (2)
N1—N2—H2120.8C13—C12—C15120.1 (2)
O6—N3—O5121.9 (2)C11—C12—C15121.6 (2)
O6—N3—C17118.9 (2)C8—C13—C12120.4 (2)
O5—N3—C17119.2 (2)C8—C13—H13119.8
O7—N4—O8123.6 (3)C12—C13—H13119.8
O7—N4—C19118.9 (3)O4—C14—H14A109.5
O8—N4—C19117.5 (3)O4—C14—H14B109.5
C6—C1—C2119.8 (3)H14A—C14—H14B109.5
C6—C1—S1120.0 (2)O4—C14—H14C109.5
C2—C1—S1120.2 (2)H14A—C14—H14C109.5
C3—C2—C1119.6 (3)H14B—C14—H14C109.5
C3—C2—H2A120.2N1—C15—C12119.0 (2)
C1—C2—H2A120.2N1—C15—H15120.5
C2—C3—C4121.8 (3)C12—C15—H15120.5
C2—C3—H3119.1N2—C16—C21119.8 (2)
C4—C3—H3119.1N2—C16—C17124.0 (2)
C3—C4—C5117.8 (3)C21—C16—C17116.1 (2)
C3—C4—C7121.2 (3)C18—C17—C16121.4 (2)
C5—C4—C7121.1 (3)C18—C17—N3116.2 (2)
C4—C5—C6121.8 (3)C16—C17—N3122.3 (2)
C4—C5—H5119.1C19—C18—C17119.5 (3)
C6—C5—H5119.1C19—C18—H18120.2
C1—C6—C5119.2 (3)C17—C18—H18120.2
C1—C6—H6120.4C18—C19—C20121.1 (3)
C5—C6—H6120.4C18—C19—N4119.0 (3)
C4—C7—H7A109.5C20—C19—N4119.8 (3)
C4—C7—H7B109.5C21—C20—C19119.5 (3)
H7A—C7—H7B109.5C21—C20—H20120.3
C4—C7—H7C109.5C19—C20—H20120.3
H7A—C7—H7C109.5C20—C21—C16122.3 (3)
H7B—C7—H7C109.5C20—C21—H21118.9
C13—C8—C9122.0 (2)C16—C21—H21118.9
C13—C8—O1119.1 (2)
O3—S1—O1—C8169.03 (17)C10—C11—C12—C15179.3 (2)
O2—S1—O1—C840.0 (2)C9—C8—C13—C124.0 (4)
C1—S1—O1—C876.21 (19)O1—C8—C13—C12179.4 (2)
C15—N1—N2—C16178.0 (2)C11—C12—C13—C81.4 (4)
O3—S1—C1—C621.5 (3)C15—C12—C13—C8177.8 (2)
O2—S1—C1—C6156.3 (2)N2—N1—C15—C12178.6 (2)
O1—S1—C1—C687.9 (3)C13—C12—C15—N10.6 (4)
O3—S1—C1—C2161.1 (2)C11—C12—C15—N1178.5 (2)
O2—S1—C1—C226.3 (3)N1—N2—C16—C210.7 (4)
O1—S1—C1—C289.5 (3)N1—N2—C16—C17179.5 (2)
C6—C1—C2—C30.1 (5)N2—C16—C17—C18177.8 (3)
S1—C1—C2—C3177.3 (2)C21—C16—C17—C181.0 (4)
C1—C2—C3—C41.4 (5)N2—C16—C17—N30.1 (4)
C2—C3—C4—C51.4 (5)C21—C16—C17—N3178.6 (2)
C2—C3—C4—C7177.9 (3)O6—N3—C17—C184.3 (4)
C3—C4—C5—C60.0 (5)O5—N3—C17—C18176.2 (3)
C7—C4—C5—C6179.3 (3)O6—N3—C17—C16173.4 (3)
C2—C1—C6—C51.3 (5)O5—N3—C17—C166.0 (4)
S1—C1—C6—C5178.7 (2)C16—C17—C18—C190.7 (4)
C4—C5—C6—C11.3 (5)N3—C17—C18—C19178.5 (2)
S1—O1—C8—C1388.0 (3)C17—C18—C19—C200.5 (4)
S1—O1—C8—C995.3 (2)C17—C18—C19—N4179.6 (3)
C14—O4—C9—C109.9 (4)O7—N4—C19—C186.7 (4)
C14—O4—C9—C8169.3 (3)O8—N4—C19—C18171.8 (3)
C13—C8—C9—O4175.8 (2)O7—N4—C19—C20174.2 (3)
O1—C8—C9—O40.8 (4)O8—N4—C19—C207.3 (4)
C13—C8—C9—C103.5 (4)C18—C19—C20—C211.4 (5)
O1—C8—C9—C10179.9 (2)N4—C19—C20—C21179.5 (3)
O4—C9—C10—C11178.8 (2)C19—C20—C21—C161.1 (5)
C8—C9—C10—C110.5 (4)N2—C16—C21—C20178.8 (3)
C9—C10—C11—C122.0 (4)C17—C16—C21—C200.1 (4)
C10—C11—C12—C131.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O50.862.042.644 (3)126
N2—H2···O5i0.862.593.315 (3)142
C7—H7A···O3ii0.962.533.396 (4)151
Symmetry codes: (i) x+3, y+1, z; (ii) x+1, y+1, z+1.
 

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