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In the title compound, C21H18N4O6·C3H7NO, the substituted o-vanillin group makes dihedral angles of 37.17 (11) and 5.68 (8)°, respectively, with the phenyl ring and the phenyl­hydrazine mean plane. The packing is stabilized by an intra­molecular N—H...O hydrogen bond and a weak non-classical intermolecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049944/sg2096sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049944/sg2096Isup2.hkl
Contains datablock I

CCDC reference: 630461

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.140
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C21 .. 5.03 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.12 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.90 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 5 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 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-(Benzyloxy)-3-methoxybenzylidene]-2-(2,4-dinitrophenyl)hydrazine dimethylformamide monosolvate top
Crystal data top
C21H18N4O6·C3H7NOZ = 2
Mr = 495.49F(000) = 520
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.244 (3) ÅCell parameters from 1391 reflections
b = 11.792 (4) Åθ = 2.4–25.6°
c = 12.789 (4) ŵ = 0.10 mm1
α = 86.261 (7)°T = 294 K
β = 87.312 (6)°Block, red
γ = 86.856 (6)°0.25 × 0.20 × 0.12 mm
V = 1237.6 (7) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4290 independent reflections
Radiation source: fine-focus sealed tube2133 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.949, Tmax = 0.988k = 914
6206 measured reflectionsl = 1115
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0526P)2 + 0.1421P]
where P = (Fo2 + 2Fc2)/3
4290 reflections(Δ/σ)max = 0.003
328 parametersΔρmax = 0.15 e Å3
36 restraintsΔρmin = 0.17 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
O10.3903 (2)0.21837 (16)0.20490 (14)0.0568 (6)
O20.2481 (3)0.1414 (2)0.04291 (16)0.0766 (7)
O31.0887 (4)0.3086 (2)0.7731 (2)0.1069 (10)
O41.1415 (3)0.1625 (2)0.85593 (19)0.0819 (7)
O51.0137 (3)0.20675 (19)0.7038 (2)0.0892 (8)
O60.8363 (3)0.23962 (17)0.58547 (17)0.0679 (6)
N10.6512 (3)0.01540 (19)0.41265 (17)0.0448 (6)
N20.7224 (3)0.06945 (19)0.48985 (16)0.0443 (6)
H20.71170.14220.49240.053*
N31.0780 (3)0.2063 (3)0.7850 (2)0.0659 (8)
N40.9180 (3)0.1730 (2)0.6438 (2)0.0558 (7)
C10.3127 (5)0.4605 (3)0.2073 (3)0.0805 (11)
H10.34930.43130.27180.097*
C20.2154 (6)0.5594 (4)0.2025 (4)0.1126 (15)
H2A0.18690.59700.26290.135*
C30.1623 (6)0.6007 (4)0.1088 (6)0.1172 (17)
H30.09680.66750.10560.141*
C40.2009 (6)0.5483 (5)0.0187 (5)0.1144 (16)
H40.16250.57870.04490.137*
C50.3006 (4)0.4465 (3)0.0234 (3)0.0818 (11)
H50.32770.40870.03710.098*
C60.3567 (4)0.4042 (2)0.1185 (2)0.0526 (8)
C70.4637 (4)0.2970 (3)0.1267 (2)0.0596 (8)
H7A0.47440.26330.05940.072*
H7B0.57110.31400.14710.072*
C80.4083 (3)0.1046 (2)0.1877 (2)0.0446 (7)
C90.3304 (3)0.0601 (3)0.1055 (2)0.0535 (8)
C100.3365 (4)0.0556 (3)0.0948 (2)0.0606 (9)
H100.28510.08510.04010.073*
C110.4201 (4)0.1280 (3)0.1664 (3)0.0621 (9)
H110.42370.20610.15940.075*
C120.4976 (4)0.0859 (2)0.2477 (2)0.0526 (8)
H120.55310.13560.29470.063*
C130.4935 (3)0.0317 (2)0.2599 (2)0.0422 (7)
C140.1738 (4)0.1077 (4)0.0480 (3)0.0865 (12)
H14A0.25030.06110.08730.130*
H14B0.14080.17410.09080.130*
H14C0.08040.06530.02690.130*
C150.5719 (3)0.0805 (2)0.3459 (2)0.0432 (7)
H150.56440.15880.35230.052*
C160.8101 (3)0.0051 (2)0.5622 (2)0.0406 (7)
C170.8145 (3)0.1157 (2)0.5619 (2)0.0459 (7)
H170.75770.14940.51220.055*
C180.9005 (3)0.1834 (2)0.6334 (2)0.0493 (7)
H180.90190.26210.63170.059*
C190.9857 (3)0.1340 (2)0.7084 (2)0.0466 (7)
C200.9885 (3)0.0189 (2)0.7114 (2)0.0463 (7)
H201.04700.01270.76170.056*
C210.9026 (3)0.0516 (2)0.6384 (2)0.0423 (7)
O70.4956 (4)0.3131 (3)0.4836 (3)0.1249 (12)
N50.3316 (4)0.4097 (3)0.5993 (3)0.0783 (9)
C220.4651 (6)0.3479 (3)0.5681 (4)0.0924 (12)
H220.54240.33040.61820.111*
C230.3054 (6)0.4395 (5)0.7071 (4)0.1401 (19)
H23A0.40110.41790.74520.210*
H23B0.21480.40030.73880.210*
H23C0.28310.52010.70890.210*
C240.2087 (6)0.4441 (4)0.5287 (4)0.1333 (18)
H24A0.24620.42810.45870.200*
H24B0.18360.52430.53180.200*
H24C0.11290.40330.54760.200*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0766 (15)0.0488 (12)0.0426 (12)0.0082 (11)0.0009 (10)0.0036 (9)
O20.0776 (17)0.0942 (17)0.0578 (14)0.0153 (13)0.0248 (12)0.0057 (13)
O30.143 (3)0.0620 (17)0.115 (2)0.0278 (17)0.0510 (18)0.0051 (16)
O40.0861 (18)0.0888 (18)0.0705 (17)0.0110 (14)0.0319 (14)0.0038 (14)
O50.104 (2)0.0621 (15)0.107 (2)0.0018 (13)0.0516 (17)0.0222 (14)
O60.0850 (17)0.0442 (12)0.0750 (15)0.0066 (11)0.0192 (13)0.0033 (11)
N10.0445 (14)0.0477 (14)0.0416 (14)0.0024 (11)0.0016 (11)0.0034 (12)
N20.0468 (15)0.0436 (13)0.0424 (14)0.0006 (11)0.0046 (11)0.0015 (11)
N30.0636 (19)0.065 (2)0.067 (2)0.0154 (15)0.0131 (15)0.0057 (16)
N40.0598 (18)0.0524 (16)0.0553 (17)0.0056 (14)0.0057 (14)0.0083 (14)
C10.098 (3)0.056 (2)0.087 (3)0.013 (2)0.012 (2)0.007 (2)
C20.127 (4)0.077 (3)0.134 (4)0.013 (3)0.001 (3)0.025 (3)
C30.099 (3)0.071 (3)0.177 (5)0.010 (2)0.012 (4)0.024 (3)
C40.098 (3)0.114 (4)0.125 (4)0.012 (3)0.038 (3)0.064 (3)
C50.087 (3)0.090 (3)0.067 (2)0.002 (2)0.018 (2)0.019 (2)
C60.0520 (19)0.0479 (18)0.057 (2)0.0057 (14)0.0058 (15)0.0071 (16)
C70.059 (2)0.058 (2)0.059 (2)0.0027 (16)0.0008 (16)0.0081 (16)
C80.0492 (18)0.0468 (18)0.0373 (17)0.0014 (14)0.0026 (14)0.0044 (14)
C90.0452 (19)0.072 (2)0.0424 (18)0.0068 (16)0.0017 (15)0.0065 (17)
C100.055 (2)0.076 (2)0.054 (2)0.0072 (18)0.0020 (16)0.0211 (18)
C110.068 (2)0.0490 (19)0.070 (2)0.0032 (17)0.0029 (19)0.0121 (17)
C120.058 (2)0.0491 (19)0.0504 (19)0.0034 (15)0.0028 (15)0.0031 (15)
C130.0439 (17)0.0474 (18)0.0347 (16)0.0020 (14)0.0067 (13)0.0039 (13)
C140.066 (2)0.137 (4)0.058 (2)0.009 (2)0.0175 (19)0.001 (2)
C150.0435 (18)0.0456 (17)0.0401 (17)0.0017 (14)0.0008 (14)0.0031 (14)
C160.0359 (16)0.0464 (17)0.0382 (16)0.0035 (13)0.0034 (13)0.0004 (13)
C170.0466 (18)0.0464 (17)0.0447 (17)0.0020 (14)0.0018 (14)0.0060 (14)
C180.0503 (19)0.0423 (17)0.0537 (19)0.0056 (14)0.0028 (15)0.0003 (14)
C190.0410 (17)0.0532 (19)0.0435 (18)0.0070 (14)0.0011 (14)0.0045 (14)
C200.0372 (17)0.060 (2)0.0410 (17)0.0003 (14)0.0007 (13)0.0044 (15)
C210.0430 (17)0.0411 (16)0.0425 (17)0.0016 (13)0.0018 (14)0.0057 (13)
O70.146 (3)0.115 (2)0.119 (2)0.001 (2)0.000 (2)0.057 (2)
N50.077 (2)0.072 (2)0.087 (2)0.0004 (17)0.0116 (18)0.0084 (17)
C220.102 (4)0.072 (3)0.104 (4)0.000 (2)0.008 (3)0.019 (2)
C230.122 (4)0.176 (5)0.127 (4)0.000 (3)0.000 (3)0.057 (4)
C240.119 (4)0.132 (4)0.149 (4)0.006 (3)0.051 (3)0.010 (3)
Geometric parameters (Å, º) top
O1—C81.373 (3)C10—C111.392 (4)
O1—C71.453 (3)C10—H100.9300
O2—C91.378 (3)C11—C121.379 (4)
O2—C141.427 (4)C11—H110.9300
O3—N31.224 (3)C12—C131.404 (4)
O4—N31.225 (3)C12—H120.9300
O5—N41.226 (3)C13—C151.466 (3)
O6—N41.241 (3)C14—H14A0.9600
N1—C151.287 (3)C14—H14B0.9600
N1—N21.379 (3)C14—H14C0.9600
N2—C161.365 (3)C15—H150.9300
N2—H20.8600C16—C211.420 (4)
N3—C191.467 (4)C16—C171.423 (4)
N4—C211.451 (3)C17—C181.370 (4)
C1—C61.377 (4)C17—H170.9300
C1—C21.378 (5)C18—C191.392 (4)
C1—H10.9300C18—H180.9300
C2—C31.347 (6)C19—C201.361 (4)
C2—H2A0.9300C20—C211.401 (4)
C3—C41.359 (6)C20—H200.9300
C3—H30.9300O7—C221.193 (4)
C4—C51.417 (6)N5—C221.345 (5)
C4—H40.9300N5—C241.414 (5)
C5—C61.374 (4)N5—C231.449 (5)
C5—H50.9300C22—H220.9300
C6—C71.502 (4)C23—H23A0.9600
C7—H7A0.9700C23—H23B0.9600
C7—H7B0.9700C23—H23C0.9600
C8—C91.401 (4)C24—H24A0.9600
C8—C131.406 (4)C24—H24B0.9600
C9—C101.379 (4)C24—H24C0.9600
C8—O1—C7117.2 (2)C13—C12—H12119.8
C9—O2—C14119.1 (3)C12—C13—C8118.3 (3)
C15—N1—N2115.9 (2)C12—C13—C15122.4 (3)
C16—N2—N1118.7 (2)C8—C13—C15119.2 (2)
C16—N2—H2120.7O2—C14—H14A109.5
N1—N2—H2120.7O2—C14—H14B109.5
O3—N3—O4123.3 (3)H14A—C14—H14B109.5
O3—N3—C19117.3 (3)O2—C14—H14C109.5
O4—N3—C19119.4 (3)H14A—C14—H14C109.5
O5—N4—O6121.9 (3)H14B—C14—H14C109.5
O5—N4—C21119.2 (3)N1—C15—C13120.2 (3)
O6—N4—C21118.8 (3)N1—C15—H15119.9
C6—C1—C2121.3 (4)C13—C15—H15119.9
C6—C1—H1119.4N2—C16—C21123.8 (2)
C2—C1—H1119.4N2—C16—C17119.7 (2)
C3—C2—C1118.8 (4)C21—C16—C17116.5 (2)
C3—C2—H2A120.6C18—C17—C16121.5 (3)
C1—C2—H2A120.6C18—C17—H17119.2
C2—C3—C4122.5 (5)C16—C17—H17119.2
C2—C3—H3118.8C17—C18—C19119.8 (3)
C4—C3—H3118.8C17—C18—H18120.1
C3—C4—C5118.8 (4)C19—C18—H18120.1
C3—C4—H4120.6C20—C19—C18121.3 (3)
C5—C4—H4120.6C20—C19—N3118.7 (3)
C6—C5—C4119.2 (4)C18—C19—N3119.9 (3)
C6—C5—H5120.4C19—C20—C21119.6 (3)
C4—C5—H5120.4C19—C20—H20120.2
C5—C6—C1119.4 (3)C21—C20—H20120.2
C5—C6—C7120.9 (3)C20—C21—C16121.1 (3)
C1—C6—C7119.7 (3)C20—C21—N4116.2 (3)
O1—C7—C6108.5 (2)C16—C21—N4122.7 (2)
O1—C7—H7A110.0C22—N5—C24121.1 (4)
C6—C7—H7A110.0C22—N5—C23121.3 (4)
O1—C7—H7B110.0C24—N5—C23117.6 (4)
C6—C7—H7B110.0O7—C22—N5127.3 (4)
H7A—C7—H7B108.4O7—C22—H22116.3
O1—C8—C9120.7 (3)N5—C22—H22116.3
O1—C8—C13118.6 (2)N5—C23—H23A109.5
C9—C8—C13120.4 (3)N5—C23—H23B109.5
O2—C9—C10125.9 (3)H23A—C23—H23B109.5
O2—C9—C8113.8 (3)N5—C23—H23C109.5
C10—C9—C8120.3 (3)H23A—C23—H23C109.5
C9—C10—C11119.5 (3)H23B—C23—H23C109.5
C9—C10—H10120.3N5—C24—H24A109.5
C11—C10—H10120.3N5—C24—H24B109.5
C12—C11—C10121.1 (3)H24A—C24—H24B109.5
C12—C11—H11119.5N5—C24—H24C109.5
C10—C11—H11119.5H24A—C24—H24C109.5
C11—C12—C13120.4 (3)H24B—C24—H24C109.5
C11—C12—H12119.8
C15—N1—N2—C16179.1 (2)C9—C8—C13—C15179.2 (2)
C6—C1—C2—C30.4 (7)N2—N1—C15—C13179.2 (2)
C1—C2—C3—C40.1 (8)C12—C13—C15—N11.4 (4)
C2—C3—C4—C50.0 (7)C8—C13—C15—N1179.6 (2)
C3—C4—C5—C60.6 (6)N1—N2—C16—C21173.2 (2)
C4—C5—C6—C11.1 (5)N1—N2—C16—C175.4 (3)
C4—C5—C6—C7179.6 (3)N2—C16—C17—C18179.8 (2)
C2—C1—C6—C51.0 (5)C21—C16—C17—C181.6 (4)
C2—C1—C6—C7179.7 (3)C16—C17—C18—C190.1 (4)
C8—O1—C7—C6145.3 (2)C17—C18—C19—C201.3 (4)
C5—C6—C7—O1125.6 (3)C17—C18—C19—N3180.0 (3)
C1—C6—C7—O153.7 (4)O3—N3—C19—C20171.9 (3)
C7—O1—C8—C968.5 (3)O4—N3—C19—C207.3 (4)
C7—O1—C8—C13117.5 (3)O3—N3—C19—C186.8 (4)
C14—O2—C9—C106.5 (4)O4—N3—C19—C18174.0 (3)
C14—O2—C9—C8175.4 (3)C18—C19—C20—C210.7 (4)
O1—C8—C9—O24.4 (4)N3—C19—C20—C21179.3 (2)
C13—C8—C9—O2178.2 (2)C19—C20—C21—C161.2 (4)
O1—C8—C9—C10173.8 (3)C19—C20—C21—N4177.2 (2)
C13—C8—C9—C100.0 (4)N2—C16—C21—C20179.2 (2)
O2—C9—C10—C11177.7 (3)C17—C16—C21—C202.2 (4)
C8—C9—C10—C110.3 (4)N2—C16—C21—N42.6 (4)
C9—C10—C11—C120.3 (5)C17—C16—C21—N4176.0 (2)
C10—C11—C12—C130.1 (4)O5—N4—C21—C206.3 (4)
C11—C12—C13—C80.1 (4)O6—N4—C21—C20175.4 (2)
C11—C12—C13—C15179.1 (2)O5—N4—C21—C16172.0 (3)
O1—C8—C13—C12173.8 (2)O6—N4—C21—C166.3 (4)
C9—C8—C13—C120.2 (4)C24—N5—C22—O71.9 (6)
O1—C8—C13—C155.2 (4)C23—N5—C22—O7175.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O60.862.052.653 (3)126
C15—H15···O70.932.583.369 (4)143
 

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