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In the title compound, C21H17N3O5, the central planar group makes dihedral angles of 83.55 (11) and 5.54 (8)° with the terminal phenyl ring and the phenyl­hydrazine mean planes, respectively. The mol­ecular packing is stabilized by inter­molecular N—H...O hydrogen bonds that link adjacent mol­ecules into one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045466/sa2021sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045466/sa2021Isup2.hkl
Contains datablock I

CCDC reference: 630446

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.069
  • wR factor = 0.159
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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No errors found in this datablock

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-[(3-Methoxy-4-benzoyloxy)benzylidene]-2-(4-nitrophenyl)hydrazine top
Crystal data top
C21H17N3O5F(000) = 816
Mr = 391.38Dx = 1.361 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2542 reflections
a = 8.1110 (16) Åθ = 3.3–23.5°
b = 14.965 (3) ŵ = 0.10 mm1
c = 16.220 (3) ÅT = 294 K
β = 104.07 (3)°Block, orange
V = 1909.7 (7) Å30.15 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3322 independent reflections
Radiation source: fine-focus sealed tube1960 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.973, Tmax = 0.990k = 1117
11378 measured reflectionsl = 1919
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0709P)2]
where P = (Fo2 + 2Fc2)/3
3322 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.15 e Å3
0 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
O10.4194 (3)0.92875 (18)0.64359 (14)0.0769 (8)
O20.2467 (2)0.91781 (16)0.73193 (14)0.0649 (7)
O30.3310 (2)1.08856 (17)0.77068 (14)0.0702 (7)
O41.4862 (3)0.74896 (18)1.41804 (19)0.0997 (10)
O51.4169 (3)0.64748 (19)1.32102 (19)0.0974 (9)
N10.8670 (3)0.93557 (18)1.06154 (15)0.0506 (7)
N20.9907 (3)0.96397 (17)1.12960 (15)0.0546 (7)
H21.00611.02031.13910.066*
N31.4068 (3)0.7241 (2)1.3477 (2)0.0693 (8)
C10.1393 (4)0.8907 (2)0.5028 (2)0.0691 (10)
H10.24450.89900.49060.083*
C20.0012 (4)0.8742 (3)0.4376 (2)0.0793 (11)
H2A0.00880.87260.38170.095*
C30.1551 (4)0.8602 (3)0.4552 (2)0.0788 (11)
H30.25000.84880.41110.095*
C40.1711 (4)0.8629 (3)0.5373 (2)0.0808 (12)
H40.27640.85280.54870.097*
C50.0310 (4)0.8805 (2)0.6032 (2)0.0671 (10)
H50.04230.88260.65880.081*
C60.1264 (3)0.8950 (2)0.5862 (2)0.0509 (8)
C70.2800 (4)0.9156 (2)0.6540 (2)0.0556 (8)
C80.3839 (3)0.9369 (2)0.80130 (19)0.0547 (8)
C90.4671 (4)0.8685 (2)0.8500 (2)0.0626 (9)
H90.43570.80960.83570.075*
C100.5977 (4)0.8864 (2)0.9203 (2)0.0596 (9)
H100.65420.83980.95350.071*
C110.6442 (3)0.9743 (2)0.94121 (18)0.0465 (7)
C120.5566 (3)1.0431 (2)0.89265 (18)0.0494 (8)
H120.58631.10200.90750.059*
C130.4245 (3)1.0254 (2)0.82169 (19)0.0521 (8)
C140.3492 (4)1.1777 (2)0.8001 (2)0.0734 (10)
H14A0.32831.18060.85580.110*
H14B0.26911.21500.76190.110*
H14C0.46251.19800.80250.110*
C150.7822 (3)0.9969 (2)1.01487 (19)0.0512 (8)
H150.80851.05661.02790.061*
C161.0899 (3)0.9037 (2)1.18255 (18)0.0455 (7)
C171.0765 (3)0.8115 (2)1.1672 (2)0.0541 (8)
H170.99760.78971.11990.065*
C181.1796 (3)0.7536 (2)1.2218 (2)0.0577 (9)
H181.17080.69241.21170.069*
C191.2967 (3)0.7862 (2)1.2919 (2)0.0523 (8)
C201.3126 (3)0.8771 (2)1.3082 (2)0.0547 (8)
H201.39190.89821.35570.066*
C211.2114 (3)0.9351 (2)1.25437 (18)0.0514 (8)
H211.22230.99621.26490.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0541 (12)0.114 (2)0.0604 (15)0.0096 (13)0.0095 (10)0.0062 (15)
O20.0530 (11)0.0894 (18)0.0468 (14)0.0139 (11)0.0015 (10)0.0081 (13)
O30.0638 (13)0.0713 (17)0.0654 (15)0.0061 (12)0.0037 (11)0.0089 (14)
O40.0877 (16)0.095 (2)0.091 (2)0.0110 (15)0.0282 (15)0.0259 (18)
O50.109 (2)0.0637 (18)0.111 (2)0.0269 (16)0.0096 (16)0.0143 (18)
N10.0431 (12)0.0611 (17)0.0440 (15)0.0048 (12)0.0032 (11)0.0051 (14)
N20.0561 (14)0.0484 (15)0.0527 (16)0.0033 (12)0.0004 (12)0.0019 (14)
N30.0542 (16)0.068 (2)0.082 (2)0.0018 (16)0.0105 (16)0.020 (2)
C10.0641 (19)0.083 (3)0.059 (2)0.0113 (18)0.0134 (17)0.005 (2)
C20.082 (2)0.096 (3)0.054 (2)0.019 (2)0.0052 (19)0.005 (2)
C30.071 (2)0.098 (3)0.056 (3)0.024 (2)0.0064 (18)0.001 (2)
C40.0593 (19)0.108 (3)0.068 (3)0.023 (2)0.0035 (18)0.005 (2)
C50.066 (2)0.077 (3)0.053 (2)0.0102 (18)0.0053 (16)0.0033 (19)
C60.0518 (16)0.0473 (18)0.049 (2)0.0071 (14)0.0035 (14)0.0032 (16)
C70.0541 (18)0.055 (2)0.054 (2)0.0001 (16)0.0071 (15)0.0000 (17)
C80.0479 (16)0.066 (2)0.048 (2)0.0086 (16)0.0065 (14)0.0076 (18)
C90.0680 (19)0.052 (2)0.063 (2)0.0051 (17)0.0068 (17)0.0051 (18)
C100.0629 (18)0.054 (2)0.056 (2)0.0043 (16)0.0030 (16)0.0038 (17)
C110.0437 (14)0.0552 (19)0.0408 (18)0.0022 (15)0.0105 (13)0.0010 (16)
C120.0484 (15)0.055 (2)0.0448 (19)0.0046 (14)0.0116 (14)0.0019 (16)
C130.0453 (15)0.061 (2)0.050 (2)0.0057 (16)0.0104 (14)0.0021 (18)
C140.070 (2)0.062 (2)0.085 (3)0.0103 (18)0.0129 (18)0.017 (2)
C150.0493 (16)0.055 (2)0.048 (2)0.0005 (15)0.0108 (14)0.0007 (16)
C160.0406 (14)0.0494 (18)0.0449 (18)0.0028 (14)0.0076 (13)0.0020 (16)
C170.0488 (16)0.054 (2)0.056 (2)0.0071 (15)0.0051 (14)0.0078 (17)
C180.0530 (17)0.0443 (19)0.073 (2)0.0016 (15)0.0108 (17)0.0008 (18)
C190.0423 (15)0.053 (2)0.060 (2)0.0012 (15)0.0102 (14)0.0139 (18)
C200.0504 (16)0.062 (2)0.0484 (19)0.0072 (16)0.0049 (14)0.0022 (18)
C210.0548 (16)0.0490 (18)0.0467 (19)0.0036 (15)0.0052 (14)0.0030 (16)
Geometric parameters (Å, º) top
O1—C71.199 (3)C8—C91.368 (4)
O2—C71.356 (4)C8—C131.385 (4)
O2—C81.406 (3)C9—C101.381 (4)
O3—C131.359 (3)C9—H90.9300
O3—C141.412 (4)C10—C111.388 (4)
O4—N31.225 (4)C10—H100.9300
O5—N31.234 (4)C11—C121.383 (4)
N1—C151.279 (3)C11—C151.464 (4)
N1—N21.366 (3)C12—C131.394 (4)
N2—C161.364 (3)C12—H120.9300
N2—H20.8600C14—H14A0.9600
N3—C191.445 (4)C14—H14B0.9600
C1—C21.375 (4)C14—H14C0.9600
C1—C61.384 (4)C15—H150.9300
C1—H10.9300C16—C171.402 (4)
C2—C31.363 (5)C16—C211.411 (4)
C2—H2A0.9300C17—C181.369 (4)
C3—C41.368 (5)C17—H170.9300
C3—H30.9300C18—C191.381 (4)
C4—C51.383 (4)C18—H180.9300
C4—H40.9300C19—C201.386 (4)
C5—C61.387 (4)C20—C211.357 (4)
C5—H50.9300C20—H200.9300
C6—C71.479 (4)C21—H210.9300
C7—O2—C8116.9 (2)C11—C10—H10120.2
C13—O3—C14117.0 (2)C12—C11—C10119.7 (3)
C15—N1—N2116.0 (2)C12—C11—C15118.5 (3)
C16—N2—N1120.5 (2)C10—C11—C15121.8 (3)
C16—N2—H2119.7C11—C12—C13120.9 (3)
N1—N2—H2119.7C11—C12—H12119.5
O4—N3—O5123.0 (3)C13—C12—H12119.5
O4—N3—C19119.5 (3)O3—C13—C8117.0 (3)
O5—N3—C19117.5 (3)O3—C13—C12125.0 (3)
C2—C1—C6120.9 (3)C8—C13—C12118.0 (3)
C2—C1—H1119.5O3—C14—H14A109.5
C6—C1—H1119.5O3—C14—H14B109.5
C3—C2—C1119.8 (4)H14A—C14—H14B109.5
C3—C2—H2A120.1O3—C14—H14C109.5
C1—C2—H2A120.1H14A—C14—H14C109.5
C2—C3—C4120.5 (3)H14B—C14—H14C109.5
C2—C3—H3119.8N1—C15—C11120.8 (3)
C4—C3—H3119.8N1—C15—H15119.6
C3—C4—C5120.2 (3)C11—C15—H15119.6
C3—C4—H4119.9N2—C16—C17122.0 (3)
C5—C4—H4119.9N2—C16—C21119.1 (3)
C4—C5—C6120.0 (3)C17—C16—C21118.9 (3)
C4—C5—H5120.0C18—C17—C16119.9 (3)
C6—C5—H5120.0C18—C17—H17120.0
C1—C6—C5118.6 (3)C16—C17—H17120.0
C1—C6—C7119.1 (3)C17—C18—C19119.9 (3)
C5—C6—C7122.3 (3)C17—C18—H18120.0
O1—C7—O2122.3 (3)C19—C18—H18120.0
O1—C7—C6125.6 (3)C18—C19—C20121.1 (3)
O2—C7—C6112.0 (3)C18—C19—N3119.0 (3)
C9—C8—C13121.5 (3)C20—C19—N3119.8 (3)
C9—C8—O2119.6 (3)C21—C20—C19119.4 (3)
C13—C8—O2118.8 (3)C21—C20—H20120.3
C8—C9—C10120.2 (3)C19—C20—H20120.3
C8—C9—H9119.9C20—C21—C16120.7 (3)
C10—C9—H9119.9C20—C21—H21119.6
C9—C10—C11119.6 (3)C16—C21—H21119.6
C9—C10—H10120.2
C15—N1—N2—C16179.0 (3)C9—C8—C13—O3178.1 (3)
C6—C1—C2—C31.2 (6)O2—C8—C13—O32.2 (4)
C1—C2—C3—C40.3 (6)C9—C8—C13—C121.6 (4)
C2—C3—C4—C50.5 (6)O2—C8—C13—C12177.5 (3)
C3—C4—C5—C60.4 (6)C11—C12—C13—O3179.6 (3)
C2—C1—C6—C51.3 (5)C11—C12—C13—C80.1 (4)
C2—C1—C6—C7178.2 (3)N2—N1—C15—C11178.7 (2)
C4—C5—C6—C10.5 (5)C12—C11—C15—N1179.8 (3)
C4—C5—C6—C7179.0 (3)C10—C11—C15—N11.4 (4)
C8—O2—C7—O10.3 (5)N1—N2—C16—C173.6 (4)
C8—O2—C7—C6179.9 (3)N1—N2—C16—C21177.2 (2)
C1—C6—C7—O10.5 (5)N2—C16—C17—C18179.6 (3)
C5—C6—C7—O1180.0 (3)C21—C16—C17—C180.4 (4)
C1—C6—C7—O2179.7 (3)C16—C17—C18—C190.0 (5)
C5—C6—C7—O20.2 (4)C17—C18—C19—C200.2 (5)
C7—O2—C8—C998.5 (3)C17—C18—C19—N3178.7 (3)
C7—O2—C8—C1385.5 (4)O4—N3—C19—C18165.4 (3)
C13—C8—C9—C101.5 (5)O5—N3—C19—C1815.1 (4)
O2—C8—C9—C10177.4 (3)O4—N3—C19—C2016.0 (4)
C8—C9—C10—C110.1 (5)O5—N3—C19—C20163.4 (3)
C9—C10—C11—C121.6 (4)C18—C19—C20—C210.0 (5)
C9—C10—C11—C15179.7 (3)N3—C19—C20—C21178.4 (3)
C10—C11—C12—C131.5 (4)C19—C20—C21—C160.5 (4)
C15—C11—C12—C13179.8 (3)N2—C16—C21—C20179.8 (3)
C14—O3—C13—C8168.1 (3)C17—C16—C21—C200.6 (4)
C14—O3—C13—C1211.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.862.062.907 (4)169
Symmetry code: (i) x+5/2, y+1/2, z+5/2.
 

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