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In the title compound, C16H16N4O6·C3H7NO, the isovanillin group makes a dihedral angle of 2.18 (13)° with the phenyl­hydrazine residue. The crystal packing is stabilized by bifurcated N—H...(O,O) intra- and inter­molecular hydrogen bonds, which form inversion-related dimers, together with inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037883/ci2169sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037883/ci2169Isup2.hkl
Contains datablock I

CCDC reference: 624177

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.043
  • wR factor = 0.146
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. O3 .. 2.63 Ang.
Alert level C PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C17 .. 2.97 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O7' .. C18' .. 3.01 Ang.
0 ALERT level A = In general: serious problem 1 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 3 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 5 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-(2-Chlorobenzyloxy)benzylidene]-2-(2,4-dinitrophenyl)hydrazine N,N'-dimethylformamide solvate top
Crystal data top
C16H16N4O6·C3H7NOF(000) = 912
Mr = 433.42Dx = 1.374 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2053 reflections
a = 10.306 (5) Åθ = 2.8–24.0°
b = 9.612 (4) ŵ = 0.11 mm1
c = 21.152 (10) ÅT = 294 K
β = 90.377 (9)°Block, red
V = 2095.3 (17) Å30.28 × 0.20 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3690 independent reflections
Radiation source: fine-focus sealed tube1991 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 126
Tmin = 0.948, Tmax = 0.987k = 119
10354 measured reflectionsl = 2225
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0639P)2 + 1.3187P]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.002
3690 reflectionsΔρmax = 0.18 e Å3
327 parametersΔρmin = 0.16 e Å3
68 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0111 (14)
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*/UeqOcc. (<1)
O10.1125 (2)0.13443 (19)0.01264 (9)0.0604 (6)
O20.01013 (19)0.29594 (18)0.06929 (9)0.0524 (5)
O30.4683 (2)1.0910 (2)0.04369 (10)0.0661 (7)
O40.4695 (2)1.2673 (2)0.10504 (11)0.0840 (8)
O50.1520 (2)1.3350 (3)0.26022 (12)0.0859 (8)
O60.0255 (3)1.1683 (3)0.28646 (12)0.0913 (9)
N10.2644 (2)0.7478 (2)0.05951 (10)0.0443 (6)
N20.3167 (2)0.8788 (2)0.06562 (10)0.0442 (6)
H2A0.38000.90500.04220.053*
N30.4247 (2)1.1554 (2)0.08868 (11)0.0514 (6)
N40.1104 (3)1.2169 (3)0.25323 (13)0.0611 (7)
C10.2670 (3)0.5271 (3)0.01090 (12)0.0424 (7)
C20.1609 (3)0.4808 (3)0.04555 (12)0.0422 (7)
H20.12260.53980.07490.051*
C30.1126 (3)0.3501 (3)0.03701 (12)0.0404 (7)
C40.1680 (3)0.2617 (3)0.00808 (13)0.0445 (7)
C50.2727 (3)0.3071 (3)0.04254 (13)0.0503 (8)
H50.31020.24900.07250.060*
C60.3222 (3)0.4397 (3)0.03262 (13)0.0479 (7)
H60.39350.46960.05570.057*
C70.1565 (3)0.0427 (3)0.06043 (15)0.0642 (9)
H7A0.14590.08600.10100.096*
H7B0.10690.04170.05920.096*
H7C0.24660.02180.05340.096*
C80.0478 (3)0.3828 (3)0.11546 (13)0.0509 (8)
H8A0.08210.46640.09590.061*
H8B0.01580.40960.14720.061*
C90.1552 (3)0.3007 (3)0.14518 (15)0.0666 (9)
H9A0.21850.27680.11350.100*
H9B0.19540.35550.17750.100*
H9C0.12030.21720.16350.100*
C100.3174 (3)0.6672 (3)0.01992 (13)0.0445 (7)
H100.38830.69760.00330.053*
C110.2666 (3)0.9647 (3)0.10909 (12)0.0385 (6)
C120.3157 (3)1.0992 (3)0.12218 (12)0.0400 (6)
C130.2644 (3)1.1812 (3)0.16877 (12)0.0438 (7)
H130.29851.26920.17670.053*
C140.1627 (3)1.1325 (3)0.20337 (13)0.0460 (7)
C150.1095 (3)1.0031 (3)0.19125 (14)0.0519 (8)
H150.03920.97190.21460.062*
C160.1597 (3)0.9224 (3)0.14552 (13)0.0487 (7)
H160.12250.83590.13770.058*
O70.5500 (6)0.0822 (10)0.1666 (2)0.1014 (18)0.815 (7)
N50.5755 (8)0.0311 (9)0.2586 (3)0.067 (3)0.815 (7)
C170.6115 (5)0.0096 (5)0.2017 (2)0.0686 (15)0.815 (7)
H17A0.69190.02090.18760.082*0.815 (7)
C180.6609 (6)0.1091 (6)0.2990 (3)0.113 (2)0.815 (7)
H18A0.74190.12400.27790.169*0.815 (7)
H18B0.67600.05820.33740.169*0.815 (7)
H18C0.62210.19720.30870.169*0.815 (7)
C190.4479 (5)0.0083 (7)0.2816 (3)0.101 (2)0.815 (7)
H19A0.39950.05200.24810.152*0.815 (7)
H19B0.40250.07320.29560.152*0.815 (7)
H19C0.45740.07210.31620.152*0.815 (7)
O7'0.550 (5)0.125 (5)0.1748 (18)0.19 (3)0.185 (7)
N5'0.547 (4)0.027 (5)0.2589 (17)0.083 (16)0.185 (7)
C17'0.510 (3)0.083 (2)0.2254 (13)0.099 (9)0.185 (7)
H17B0.44410.13620.24330.119*0.185 (7)
C18'0.499 (3)0.066 (3)0.3205 (12)0.105 (9)0.185 (7)
H18D0.56820.06330.35090.157*0.185 (7)
H18E0.43170.00270.33290.157*0.185 (7)
H18F0.46400.15890.31860.157*0.185 (7)
C19'0.660 (3)0.108 (4)0.241 (2)0.177 (16)0.185 (7)
H19D0.67070.10420.19600.266*0.185 (7)
H19E0.73580.07160.26150.266*0.185 (7)
H19F0.64770.20350.25360.266*0.185 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0771 (15)0.0394 (11)0.0649 (14)0.0134 (10)0.0153 (11)0.0151 (10)
O20.0586 (13)0.0442 (11)0.0546 (12)0.0122 (10)0.0157 (10)0.0087 (9)
O30.0820 (16)0.0530 (13)0.0637 (14)0.0188 (11)0.0363 (12)0.0153 (11)
O40.0991 (19)0.0639 (14)0.0896 (17)0.0460 (14)0.0393 (14)0.0329 (13)
O50.0773 (17)0.0740 (17)0.107 (2)0.0078 (14)0.0281 (15)0.0430 (15)
O60.102 (2)0.0854 (18)0.0868 (18)0.0025 (15)0.0548 (17)0.0076 (14)
N10.0540 (14)0.0353 (12)0.0437 (13)0.0088 (11)0.0017 (11)0.0025 (10)
N20.0533 (15)0.0366 (12)0.0427 (13)0.0112 (11)0.0096 (11)0.0031 (10)
N30.0616 (16)0.0423 (14)0.0507 (15)0.0140 (12)0.0163 (13)0.0076 (12)
N40.0583 (17)0.0637 (18)0.0614 (17)0.0102 (15)0.0138 (14)0.0086 (15)
C10.0486 (17)0.0385 (15)0.0402 (16)0.0030 (13)0.0033 (13)0.0002 (12)
C20.0523 (17)0.0361 (15)0.0381 (15)0.0042 (13)0.0053 (13)0.0061 (12)
C30.0450 (16)0.0362 (15)0.0402 (15)0.0068 (13)0.0027 (13)0.0002 (12)
C40.0550 (18)0.0345 (15)0.0441 (16)0.0041 (13)0.0025 (14)0.0049 (12)
C50.060 (2)0.0419 (16)0.0492 (17)0.0024 (14)0.0083 (15)0.0082 (13)
C60.0505 (18)0.0473 (17)0.0461 (17)0.0061 (14)0.0093 (14)0.0023 (13)
C70.083 (2)0.0474 (18)0.063 (2)0.0028 (17)0.0029 (18)0.0191 (16)
C80.0526 (18)0.0512 (17)0.0490 (17)0.0041 (15)0.0056 (14)0.0069 (14)
C90.061 (2)0.073 (2)0.066 (2)0.0096 (17)0.0161 (17)0.0020 (17)
C100.0488 (17)0.0429 (16)0.0419 (16)0.0091 (14)0.0057 (13)0.0009 (13)
C110.0435 (16)0.0368 (14)0.0353 (15)0.0028 (12)0.0008 (12)0.0003 (12)
C120.0432 (16)0.0365 (14)0.0403 (15)0.0052 (12)0.0056 (13)0.0025 (12)
C130.0472 (17)0.0382 (15)0.0460 (16)0.0029 (13)0.0030 (14)0.0013 (13)
C140.0470 (17)0.0461 (17)0.0451 (17)0.0072 (14)0.0059 (14)0.0032 (13)
C150.0504 (18)0.0514 (18)0.0542 (18)0.0017 (15)0.0151 (15)0.0045 (15)
C160.0481 (18)0.0438 (16)0.0544 (18)0.0097 (14)0.0102 (15)0.0018 (14)
O70.089 (3)0.133 (4)0.081 (3)0.007 (3)0.017 (2)0.024 (3)
N50.057 (4)0.078 (4)0.065 (4)0.002 (3)0.000 (2)0.011 (2)
C170.061 (3)0.076 (3)0.069 (3)0.000 (2)0.003 (2)0.007 (2)
C180.125 (5)0.100 (4)0.112 (4)0.002 (3)0.034 (4)0.032 (3)
C190.077 (3)0.148 (5)0.079 (4)0.013 (3)0.012 (3)0.034 (4)
O7'0.19 (3)0.19 (3)0.19 (3)0.004 (10)0.002 (10)0.001 (10)
N5'0.088 (18)0.077 (17)0.083 (18)0.004 (9)0.009 (9)0.002 (9)
C17'0.099 (12)0.095 (11)0.104 (12)0.007 (9)0.006 (9)0.005 (9)
C18'0.110 (12)0.108 (12)0.096 (12)0.001 (9)0.012 (9)0.004 (9)
C19'0.177 (18)0.172 (18)0.183 (18)0.002 (10)0.002 (10)0.013 (10)
Geometric parameters (Å, º) top
O1—C41.353 (3)C10—H100.93
O1—C71.418 (3)C11—C161.409 (4)
O2—C31.365 (3)C11—C121.415 (3)
O2—C81.419 (3)C12—C131.371 (3)
O3—N31.224 (3)C13—C141.365 (4)
O4—N31.219 (3)C13—H130.93
O5—N41.222 (3)C14—C151.383 (4)
O6—N41.219 (3)C15—C161.346 (4)
N1—C101.267 (3)C15—H150.93
N1—N21.376 (3)C16—H160.93
N2—C111.342 (3)O7—C171.197 (6)
N2—H2A0.86N5—C171.321 (5)
N3—C121.437 (3)N5—C181.434 (6)
N4—C141.438 (4)N5—C191.456 (7)
C1—C61.372 (4)C17—H17A0.93
C1—C21.393 (4)C18—H18A0.96
C1—C101.456 (4)C18—H18B0.96
C2—C31.363 (3)C18—H18C0.96
C2—H20.93C19—H19A0.96
C3—C41.402 (3)C19—H19B0.96
C4—C51.377 (4)C19—H19C0.96
C5—C61.389 (4)O7'—C17'1.217 (10)
C5—H50.93N5'—C17'1.332 (10)
C6—H60.93N5'—C18'1.449 (10)
C7—H7A0.96N5'—C19'1.451 (10)
C7—H7B0.96C17'—H17B0.93
C7—H7C0.96C18'—H18D0.96
C8—C91.501 (4)C18'—H18E0.96
C8—H8A0.97C18'—H18F0.96
C8—H8B0.97C19'—H19D0.96
C9—H9A0.96C19'—H19E0.96
C9—H9B0.96C19'—H19F0.96
C9—H9C0.96
C4—O1—C7118.4 (2)C16—C11—C12115.9 (2)
C3—O2—C8116.7 (2)C13—C12—C11121.8 (2)
C10—N1—N2116.8 (2)C13—C12—N3116.4 (2)
C11—N2—N1118.4 (2)C11—C12—N3121.8 (2)
C11—N2—H2A120.8C14—C13—C12119.3 (3)
N1—N2—H2A120.8C14—C13—H13120.3
O4—N3—O3121.7 (2)C12—C13—H13120.3
O4—N3—C12119.2 (2)C13—C14—C15121.0 (3)
O3—N3—C12119.1 (2)C13—C14—N4119.5 (3)
O6—N4—O5122.6 (3)C15—C14—N4119.5 (3)
O6—N4—C14118.8 (3)C16—C15—C14119.8 (3)
O5—N4—C14118.7 (3)C16—C15—H15120.1
C6—C1—C2119.2 (2)C14—C15—H15120.1
C6—C1—C10120.3 (3)C15—C16—C11122.2 (3)
C2—C1—C10120.4 (2)C15—C16—H16118.9
C3—C2—C1120.8 (2)C11—C16—H16118.9
C3—C2—H2119.6C17—N5—C18121.5 (6)
C1—C2—H2119.6C17—N5—C19119.1 (6)
C2—C3—O2124.7 (2)C18—N5—C19119.3 (5)
C2—C3—C4119.9 (2)O7—C17—N5126.0 (5)
O2—C3—C4115.4 (2)O7—C17—H17A117.0
O1—C4—C5125.5 (2)N5—C17—H17A117.0
O1—C4—C3115.0 (2)N5—C18—H18A109.5
C5—C4—C3119.4 (2)N5—C18—H18B109.5
C4—C5—C6120.0 (3)H18A—C18—H18B109.5
C4—C5—H5120.0N5—C18—H18C109.5
C6—C5—H5120.0H18A—C18—H18C109.5
C1—C6—C5120.6 (3)H18B—C18—H18C109.5
C1—C6—H6119.7N5—C19—H19A109.5
C5—C6—H6119.7N5—C19—H19B109.5
O1—C7—H7A109.5H19A—C19—H19B109.5
O1—C7—H7B109.5N5—C19—H19C109.5
H7A—C7—H7B109.5H19A—C19—H19C109.5
O1—C7—H7C109.5H19B—C19—H19C109.5
H7A—C7—H7C109.5C17'—N5'—C18'126 (3)
H7B—C7—H7C109.5C17'—N5'—C19'121 (3)
O2—C8—C9107.1 (2)C18'—N5'—C19'112 (3)
O2—C8—H8A110.3O7'—C17'—N5'129 (4)
C9—C8—H8A110.3O7'—C17'—H17B115.4
O2—C8—H8B110.3N5'—C17'—H17B115.4
C9—C8—H8B110.3N5'—C18'—H18D109.5
H8A—C8—H8B108.6N5'—C18'—H18E109.5
C8—C9—H9A109.5H18D—C18'—H18E109.5
C8—C9—H9B109.5N5'—C18'—H18F109.5
H9A—C9—H9B109.5H18D—C18'—H18F109.5
C8—C9—H9C109.5H18E—C18'—H18F109.5
H9A—C9—H9C109.5N5'—C19'—H19D109.5
H9B—C9—H9C109.5N5'—C19'—H19E109.5
N1—C10—C1119.8 (2)H19D—C19'—H19E109.5
N1—C10—H10120.1N5'—C19'—H19F109.5
C1—C10—H10120.1H19D—C19'—H19F109.5
N2—C11—C16120.2 (2)H19E—C19'—H19F109.5
N2—C11—C12123.9 (2)
C10—N1—N2—C11177.1 (2)C16—C11—C12—C131.8 (4)
C6—C1—C2—C30.5 (4)N2—C11—C12—N30.6 (4)
C10—C1—C2—C3179.5 (3)C16—C11—C12—N3179.9 (2)
C1—C2—C3—O2179.3 (2)O4—N3—C12—C133.8 (4)
C1—C2—C3—C41.4 (4)O3—N3—C12—C13174.8 (3)
C8—O2—C3—C20.9 (4)O4—N3—C12—C11174.4 (3)
C8—O2—C3—C4179.8 (2)O3—N3—C12—C117.0 (4)
C7—O1—C4—C56.0 (4)C11—C12—C13—C140.3 (4)
C7—O1—C4—C3175.3 (3)N3—C12—C13—C14178.5 (2)
C2—C3—C4—O1180.0 (2)C12—C13—C14—C151.3 (4)
O2—C3—C4—O10.7 (4)C12—C13—C14—N4178.6 (2)
C2—C3—C4—C51.2 (4)O6—N4—C14—C13175.2 (3)
O2—C3—C4—C5179.4 (2)O5—N4—C14—C135.6 (4)
O1—C4—C5—C6178.8 (3)O6—N4—C14—C154.7 (4)
C3—C4—C5—C60.2 (4)O5—N4—C14—C15174.6 (3)
C2—C1—C6—C50.5 (4)C13—C14—C15—C161.2 (4)
C10—C1—C6—C5178.4 (3)N4—C14—C15—C16178.6 (3)
C4—C5—C6—C10.7 (4)C14—C15—C16—C110.4 (5)
C3—O2—C8—C9178.9 (2)N2—C11—C16—C15177.4 (3)
N2—N1—C10—C1179.9 (2)C12—C11—C16—C151.8 (4)
C6—C1—C10—N1178.9 (3)C18—N5—C17—O7174.9 (8)
C2—C1—C10—N10.1 (4)C19—N5—C17—O72.9 (14)
N1—N2—C11—C162.5 (4)C18'—N5'—C17'—O7'177 (5)
N1—N2—C11—C12176.7 (2)C19'—N5'—C17'—O7'8 (8)
N2—C11—C12—C13177.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.012.613 (3)127
N2—H2A···O3i0.862.403.226 (3)160
C19—H19C···O4ii0.962.393.332 (6)167
C15—H15···O5iii0.932.433.311 (4)158
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y3/2, z+1/2; (iii) x, y1/2, z+1/2.
 

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