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In the title compound, C26H24N4O5, the vanillin group makes dihedral angles of 6.82 (9), 49.91 (7) and 51.12 (8)°, respectively, with the pyrazolone ring, the nitro­benzene ring and the terminal phenyl ring. The crystal structure is stabilized by weak non-classical inter­molecular C—H...O=C and C—H...O=N hydrogen-bonding inter­actions, forming infinite networks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043613/at2130sup1.cif
Contains datablocks I, 60917b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043613/at2130Isup2.hkl
Contains datablock I

CCDC reference: 627299

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.123
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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)-4-[4-(4-Nitrobenzyloxy)-3-methoxybenzylideneamino] -1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one top
Crystal data top
C26H24N4O5F(000) = 992
Mr = 472.49Dx = 1.298 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2479 reflections
a = 17.108 (3) Åθ = 2.4–23.4°
b = 7.4848 (13) ŵ = 0.09 mm1
c = 19.203 (3) ÅT = 294 K
β = 100.408 (3)°Block, yellow
V = 2418.5 (7) Å30.22 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
4231 independent reflections
Radiation source: fine-focus sealed tube2405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2017
Tmin = 0.968, Tmax = 0.991k = 86
10806 measured reflectionsl = 2222
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.2425P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4231 reflectionsΔρmax = 0.23 e Å3
329 parametersΔρmin = 0.17 e Å3
20 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0081 (8)
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)
O10.04003 (12)0.4509 (3)0.06237 (11)0.0951 (8)
O20.0152 (4)0.2208 (11)0.0244 (7)0.093 (3)0.63 (3)
O2'0.0098 (14)0.1761 (19)0.0517 (9)0.105 (5)0.37 (3)
O30.33918 (9)0.3279 (2)0.22664 (8)0.0540 (5)
O40.35899 (9)0.6013 (2)0.30778 (8)0.0518 (5)
O50.76409 (10)0.2500 (2)0.53817 (9)0.0607 (5)
N10.04425 (15)0.3175 (4)0.02690 (14)0.0811 (8)
N20.62510 (10)0.5115 (2)0.47574 (9)0.0411 (5)
N30.80232 (11)0.4961 (2)0.61085 (10)0.0472 (5)
N40.76715 (11)0.6604 (2)0.62252 (10)0.0457 (5)
C10.23953 (15)0.3864 (4)0.08978 (13)0.0588 (7)
H10.27790.47540.09960.071*
C20.17213 (15)0.4185 (4)0.04030 (13)0.0589 (7)
H20.16470.52690.01640.071*
C30.11659 (15)0.2863 (4)0.02750 (13)0.0590 (7)
C40.12602 (18)0.1263 (4)0.06140 (16)0.0846 (10)
H40.08720.03850.05150.101*
C50.19417 (17)0.0959 (4)0.11074 (15)0.0758 (9)
H50.20110.01300.13440.091*
C60.25168 (14)0.2254 (3)0.12515 (12)0.0494 (6)
C70.32746 (15)0.1884 (3)0.17617 (13)0.0593 (7)
H7A0.32380.07460.19960.071*
H7B0.37180.18310.15110.071*
C80.40755 (13)0.3266 (3)0.27640 (11)0.0411 (6)
C90.46448 (14)0.1941 (3)0.28421 (12)0.0463 (6)
H90.45830.09580.25410.056*
C100.53119 (14)0.2081 (3)0.33739 (12)0.0469 (6)
H100.56960.11880.34230.056*
C110.54159 (13)0.3521 (3)0.38309 (11)0.0390 (6)
C120.48316 (12)0.4863 (3)0.37447 (11)0.0395 (6)
H120.48900.58360.40510.047*
C130.41765 (12)0.4760 (3)0.32169 (11)0.0383 (6)
C140.37173 (16)0.7668 (3)0.34392 (14)0.0627 (8)
H14A0.37690.74700.39390.094*
H14B0.32750.84460.32820.094*
H14C0.41950.82080.33410.094*
C150.61209 (13)0.3687 (3)0.43889 (11)0.0432 (6)
H150.64780.27420.44760.052*
C160.69101 (12)0.5309 (3)0.52958 (11)0.0385 (6)
C170.75309 (13)0.4059 (3)0.55540 (12)0.0434 (6)
C180.70338 (13)0.6826 (3)0.57009 (11)0.0395 (6)
C190.65670 (15)0.8511 (3)0.56209 (13)0.0545 (7)
H19A0.63570.87290.60440.082*
H19B0.61380.84070.52250.082*
H19C0.69050.94860.55420.082*
C200.81684 (15)0.8020 (3)0.65919 (14)0.0633 (8)
H20A0.85420.84080.63060.095*
H20B0.84510.75770.70360.095*
H20C0.78400.90080.66760.095*
C210.85111 (13)0.4043 (3)0.66828 (13)0.0486 (7)
C220.83611 (14)0.4152 (4)0.73683 (14)0.0570 (7)
H220.79460.48540.74670.068*
C230.88341 (17)0.3209 (4)0.79011 (16)0.0711 (8)
H230.87470.32980.83640.085*
C240.94362 (19)0.2134 (4)0.77501 (19)0.0807 (10)
H240.97480.14860.81100.097*
C250.95765 (17)0.2017 (4)0.70737 (19)0.0818 (10)
H250.99810.12800.69750.098*
C260.91203 (15)0.2988 (4)0.65315 (15)0.0643 (8)
H260.92240.29290.60730.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0828 (16)0.119 (2)0.0742 (15)0.0099 (13)0.0100 (12)0.0341 (14)
O20.054 (3)0.093 (4)0.118 (5)0.024 (2)0.021 (3)0.005 (3)
O2'0.089 (8)0.115 (7)0.096 (7)0.042 (6)0.028 (6)0.012 (5)
O30.0453 (10)0.0604 (11)0.0504 (10)0.0051 (8)0.0069 (8)0.0203 (9)
O40.0448 (10)0.0439 (10)0.0623 (11)0.0088 (8)0.0024 (8)0.0114 (8)
O50.0598 (11)0.0466 (11)0.0686 (12)0.0142 (8)0.0077 (9)0.0193 (9)
N10.0692 (18)0.092 (2)0.0720 (18)0.0251 (16)0.0141 (15)0.0085 (16)
N20.0417 (11)0.0412 (12)0.0390 (11)0.0007 (9)0.0039 (9)0.0041 (9)
N30.0449 (11)0.0433 (12)0.0481 (12)0.0080 (9)0.0055 (10)0.0096 (10)
N40.0458 (12)0.0401 (12)0.0475 (12)0.0006 (9)0.0010 (10)0.0091 (9)
C10.0503 (16)0.0591 (18)0.0621 (17)0.0195 (13)0.0032 (14)0.0051 (14)
C20.0587 (17)0.0603 (17)0.0546 (17)0.0133 (14)0.0018 (14)0.0063 (13)
C30.0520 (17)0.0703 (19)0.0492 (16)0.0159 (14)0.0057 (13)0.0073 (14)
C40.071 (2)0.079 (2)0.091 (2)0.0367 (17)0.0205 (18)0.0170 (19)
C50.071 (2)0.0687 (19)0.077 (2)0.0211 (16)0.0153 (17)0.0168 (16)
C60.0475 (15)0.0562 (17)0.0422 (14)0.0053 (12)0.0018 (12)0.0098 (13)
C70.0614 (17)0.0590 (17)0.0521 (16)0.0010 (13)0.0040 (14)0.0216 (13)
C80.0360 (13)0.0477 (15)0.0380 (13)0.0016 (11)0.0026 (11)0.0044 (11)
C90.0466 (15)0.0470 (15)0.0437 (14)0.0008 (11)0.0045 (12)0.0143 (11)
C100.0437 (14)0.0460 (15)0.0485 (15)0.0089 (11)0.0016 (12)0.0081 (12)
C110.0393 (13)0.0404 (14)0.0362 (13)0.0005 (10)0.0035 (11)0.0017 (11)
C120.0417 (14)0.0385 (14)0.0383 (13)0.0036 (11)0.0068 (11)0.0063 (11)
C130.0352 (13)0.0384 (14)0.0419 (14)0.0011 (10)0.0087 (11)0.0009 (11)
C140.0664 (18)0.0404 (15)0.0773 (19)0.0109 (13)0.0022 (15)0.0079 (14)
C150.0414 (14)0.0438 (15)0.0421 (14)0.0056 (11)0.0017 (11)0.0003 (12)
C160.0388 (13)0.0395 (14)0.0353 (13)0.0007 (10)0.0016 (11)0.0029 (11)
C170.0413 (14)0.0432 (15)0.0432 (14)0.0013 (11)0.0007 (11)0.0093 (12)
C180.0413 (14)0.0382 (14)0.0384 (13)0.0015 (10)0.0055 (11)0.0001 (11)
C190.0604 (17)0.0436 (15)0.0587 (16)0.0054 (12)0.0090 (13)0.0038 (12)
C200.0612 (18)0.0566 (17)0.0676 (18)0.0115 (13)0.0003 (15)0.0190 (14)
C210.0376 (14)0.0457 (15)0.0564 (17)0.0015 (11)0.0077 (12)0.0094 (13)
C220.0428 (15)0.0662 (18)0.0571 (18)0.0004 (12)0.0042 (13)0.0003 (14)
C230.0617 (19)0.083 (2)0.0609 (18)0.0056 (17)0.0093 (16)0.0101 (16)
C240.071 (2)0.071 (2)0.083 (2)0.0066 (17)0.0315 (19)0.0018 (18)
C250.0582 (19)0.078 (2)0.097 (3)0.0244 (15)0.0206 (19)0.021 (2)
C260.0478 (16)0.0697 (19)0.0680 (19)0.0124 (14)0.0090 (14)0.0182 (15)
Geometric parameters (Å, º) top
O1—N11.203 (3)C9—H90.9300
O2—N11.256 (5)C10—C111.381 (3)
O2'—N11.262 (9)C10—H100.9300
O3—C81.370 (2)C11—C121.406 (3)
O3—C71.414 (3)C11—C151.467 (3)
O4—C131.364 (2)C12—C131.371 (3)
O4—C141.417 (3)C12—H120.9300
O5—C171.237 (3)C14—H14A0.9600
N1—C31.487 (3)C14—H14B0.9600
N2—C151.278 (3)C14—H14C0.9600
N2—C161.393 (3)C15—H150.9300
N3—N41.404 (2)C16—C181.371 (3)
N3—C171.405 (3)C16—C171.435 (3)
N3—C211.433 (3)C18—C191.486 (3)
N4—C181.355 (3)C19—H19A0.9600
N4—C201.458 (3)C19—H19B0.9600
C1—C21.376 (3)C19—H19C0.9600
C1—C61.380 (3)C20—H20A0.9600
C1—H10.9300C20—H20B0.9600
C2—C31.363 (3)C20—H20C0.9600
C2—H20.9300C21—C261.380 (3)
C3—C41.359 (4)C21—C221.388 (3)
C4—C51.382 (4)C22—C231.379 (3)
C4—H40.9300C22—H220.9300
C5—C61.373 (3)C23—C241.379 (4)
C5—H50.9300C23—H230.9300
C6—C71.503 (3)C24—C251.366 (4)
C7—H7A0.9700C24—H240.9300
C7—H7B0.9700C25—C261.389 (4)
C8—C91.379 (3)C25—H250.9300
C8—C131.408 (3)C26—H260.9300
C9—C101.391 (3)
C8—O3—C7118.03 (17)C11—C12—H12119.5
C13—O4—C14117.53 (17)O4—C13—C12125.5 (2)
O1—N1—O2122.2 (4)O4—C13—C8114.91 (18)
O1—N1—O2'120.4 (6)C12—C13—C8119.6 (2)
O1—N1—C3119.0 (2)O4—C14—H14A109.5
O2—N1—C3117.4 (4)O4—C14—H14B109.5
O2'—N1—C3113.9 (8)H14A—C14—H14B109.5
C15—N2—C16122.34 (19)O4—C14—H14C109.5
N4—N3—C17109.02 (17)H14A—C14—H14C109.5
N4—N3—C21120.24 (18)H14B—C14—H14C109.5
C17—N3—C21122.63 (19)N2—C15—C11120.9 (2)
C18—N4—N3107.45 (17)N2—C15—H15119.6
C18—N4—C20126.2 (2)C11—C15—H15119.6
N3—N4—C20118.97 (19)C18—C16—N2121.9 (2)
C2—C1—C6121.7 (2)C18—C16—C17108.37 (19)
C2—C1—H1119.2N2—C16—C17129.6 (2)
C6—C1—H1119.2O5—C17—N3123.8 (2)
C3—C2—C1117.9 (2)O5—C17—C16131.4 (2)
C3—C2—H2121.1N3—C17—C16104.70 (19)
C1—C2—H2121.1N4—C18—C16109.93 (19)
C4—C3—C2122.3 (2)N4—C18—C19121.8 (2)
C4—C3—N1119.1 (2)C16—C18—C19128.3 (2)
C2—C3—N1118.5 (2)C18—C19—H19A109.5
C3—C4—C5119.1 (2)C18—C19—H19B109.5
C3—C4—H4120.4H19A—C19—H19B109.5
C5—C4—H4120.4C18—C19—H19C109.5
C6—C5—C4120.4 (3)H19A—C19—H19C109.5
C6—C5—H5119.8H19B—C19—H19C109.5
C4—C5—H5119.8N4—C20—H20A109.5
C5—C6—C1118.6 (2)N4—C20—H20B109.5
C5—C6—C7120.2 (2)H20A—C20—H20B109.5
C1—C6—C7121.1 (2)N4—C20—H20C109.5
O3—C7—C6108.0 (2)H20A—C20—H20C109.5
O3—C7—H7A110.1H20B—C20—H20C109.5
C6—C7—H7A110.1C26—C21—C22120.6 (2)
O3—C7—H7B110.1C26—C21—N3118.0 (2)
C6—C7—H7B110.1C22—C21—N3121.3 (2)
H7A—C7—H7B108.4C23—C22—C21119.3 (3)
O3—C8—C9125.3 (2)C23—C22—H22120.4
O3—C8—C13114.77 (19)C21—C22—H22120.4
C9—C8—C13119.9 (2)C24—C23—C22120.2 (3)
C8—C9—C10119.7 (2)C24—C23—H23119.9
C8—C9—H9120.2C22—C23—H23119.9
C10—C9—H9120.2C25—C24—C23120.3 (3)
C11—C10—C9121.3 (2)C25—C24—H24119.9
C11—C10—H10119.3C23—C24—H24119.9
C9—C10—H10119.3C24—C25—C26120.5 (3)
C10—C11—C12118.40 (19)C24—C25—H25119.7
C10—C11—C15121.7 (2)C26—C25—H25119.7
C12—C11—C15119.9 (2)C21—C26—C25119.0 (3)
C13—C12—C11121.1 (2)C21—C26—H26120.5
C13—C12—H12119.5C25—C26—H26120.5
C17—N3—N4—C187.7 (2)C9—C8—C13—O4178.0 (2)
C21—N3—N4—C18157.1 (2)O3—C8—C13—C12178.53 (19)
C17—N3—N4—C20159.5 (2)C9—C8—C13—C121.7 (3)
C21—N3—N4—C2051.1 (3)C16—N2—C15—C11179.3 (2)
C6—C1—C2—C30.7 (4)C10—C11—C15—N2172.4 (2)
C1—C2—C3—C40.4 (4)C12—C11—C15—N26.6 (3)
C1—C2—C3—N1178.7 (2)C15—N2—C16—C18178.2 (2)
O1—N1—C3—C4171.8 (3)C15—N2—C16—C171.7 (4)
O2—N1—C3—C421.3 (9)N4—N3—C17—O5172.0 (2)
O2'—N1—C3—C420.2 (15)C21—N3—C17—O523.4 (4)
O1—N1—C3—C26.6 (4)N4—N3—C17—C165.7 (2)
O2—N1—C3—C2160.3 (8)C21—N3—C17—C16154.3 (2)
O2'—N1—C3—C2158.2 (15)C18—C16—C17—O5175.6 (2)
C2—C3—C4—C50.1 (5)N2—C16—C17—O51.3 (4)
N1—C3—C4—C5178.5 (3)C18—C16—C17—N31.8 (3)
C3—C4—C5—C60.2 (5)N2—C16—C17—N3178.7 (2)
C4—C5—C6—C10.5 (4)N3—N4—C18—C166.5 (2)
C4—C5—C6—C7177.0 (3)C20—N4—C18—C16155.7 (2)
C2—C1—C6—C50.8 (4)N3—N4—C18—C19174.0 (2)
C2—C1—C6—C7176.7 (2)C20—N4—C18—C1924.8 (4)
C8—O3—C7—C6176.5 (2)N2—C16—C18—N4174.24 (19)
C5—C6—C7—O3128.5 (3)C17—C16—C18—N43.0 (3)
C1—C6—C7—O354.1 (3)N2—C16—C18—C195.2 (4)
C7—O3—C8—C94.0 (3)C17—C16—C18—C19177.5 (2)
C7—O3—C8—C13175.8 (2)N4—N3—C21—C26149.9 (2)
O3—C8—C9—C10179.5 (2)C17—N3—C21—C2664.9 (3)
C13—C8—C9—C100.7 (3)N4—N3—C21—C2232.5 (3)
C8—C9—C10—C110.4 (4)C17—N3—C21—C22112.7 (3)
C9—C10—C11—C120.5 (3)C26—C21—C22—C230.8 (4)
C9—C10—C11—C15179.4 (2)N3—C21—C22—C23178.3 (2)
C10—C11—C12—C130.5 (3)C21—C22—C23—C241.7 (4)
C15—C11—C12—C13178.5 (2)C22—C23—C24—C251.0 (5)
C14—O4—C13—C129.4 (3)C23—C24—C25—C260.6 (5)
C14—O4—C13—C8170.3 (2)C22—C21—C26—C250.8 (4)
C11—C12—C13—O4178.1 (2)N3—C21—C26—C25176.9 (2)
C11—C12—C13—C81.6 (3)C24—C25—C26—C211.5 (4)
O3—C8—C13—O41.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O5i0.932.413.196 (3)142
C4—H4···O2ii0.932.313.219 (7)167
C20—H20A···O1i0.962.553.513 (4)176
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y, z.
 

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