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In the title compound, C21H19N3O4, the central benzene ring makes dihedral angles of 75.46 (6) and 4.07 (6)° with the terminal benzene ring and the phenyl­hydrazine mean plane, respectively. The packing is stabilized by inter­molecular N—H...O hydrogen bonds and weak non-classical inter­molecular C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039237/at2123sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039237/at2123Isup2.hkl
Contains datablock I

CCDC reference: 623982

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.105
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C19 .. 6.71 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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-(4-Nitrophenyl)-2-[4-(2-phenoxyethoxy)benzylidene]hydrazine top
Crystal data top
C21H19N3O4F(000) = 1584
Mr = 377.39Dx = 1.338 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2517 reflections
a = 16.850 (5) Åθ = 2.2–25.8°
b = 14.868 (4) ŵ = 0.09 mm1
c = 15.190 (4) ÅT = 294 K
β = 100.120 (5)°Block, red
V = 3746.3 (18) Å30.34 × 0.28 × 0.22 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3794 independent reflections
Radiation source: fine-focus sealed tube2184 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.948, Tmax = 0.980k = 1818
10330 measured reflectionsl = 718
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2798P]
where P = (Fo2 + 2Fc2)/3
3794 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.14 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
O10.05408 (6)0.39969 (8)0.99268 (7)0.0522 (3)
O20.22788 (6)0.40318 (7)0.99288 (8)0.0507 (3)
O30.77767 (9)0.90345 (10)0.71041 (10)0.0804 (5)
O40.67593 (9)0.96501 (10)0.75680 (10)0.0810 (5)
N10.53971 (7)0.54896 (9)0.85455 (9)0.0417 (3)
N20.61073 (7)0.55912 (9)0.82462 (9)0.0447 (4)
H20.63900.51270.81630.054*
N30.71610 (10)0.89833 (11)0.74445 (11)0.0603 (4)
C10.06268 (9)0.31426 (12)0.95732 (12)0.0485 (5)
H10.05570.31570.89800.058*
C20.12666 (10)0.26838 (13)0.98048 (14)0.0582 (5)
H2A0.16290.23910.93650.070*
C30.13770 (11)0.26530 (15)1.06787 (14)0.0682 (6)
H30.18010.23281.08380.082*
C40.08482 (11)0.31121 (15)1.13112 (14)0.0707 (6)
H40.09270.31081.19020.085*
C50.02044 (10)0.35782 (13)1.10941 (12)0.0531 (5)
H50.01470.38861.15320.064*
C60.00862 (9)0.35829 (11)1.02203 (11)0.0412 (4)
C70.11443 (9)0.43974 (12)1.05829 (12)0.0529 (5)
H7A0.13650.39521.10250.063*
H7B0.09100.48781.08850.063*
C80.17973 (9)0.47638 (12)1.01383 (12)0.0533 (5)
H8A0.15650.50810.95960.064*
H8B0.21270.51831.05340.064*
C90.29685 (9)0.42377 (11)0.96183 (10)0.0404 (4)
C100.31963 (9)0.51058 (12)0.94273 (11)0.0470 (4)
H100.28670.55910.95040.056*
C110.39089 (9)0.52434 (11)0.91258 (11)0.0460 (4)
H110.40590.58270.90080.055*
C120.44122 (9)0.45347 (11)0.89921 (10)0.0394 (4)
C130.41682 (10)0.36718 (12)0.91774 (11)0.0462 (4)
H130.44930.31850.90920.055*
C140.34572 (9)0.35218 (11)0.94843 (11)0.0458 (4)
H140.33060.29380.96010.055*
C150.51692 (9)0.46924 (11)0.86831 (10)0.0432 (4)
H150.54900.42070.85850.052*
C160.63687 (9)0.64299 (11)0.80797 (10)0.0376 (4)
C170.59498 (10)0.72012 (11)0.82610 (11)0.0472 (4)
H170.54890.71460.85150.057*
C180.62151 (10)0.80370 (12)0.80666 (12)0.0484 (4)
H180.59340.85490.81850.058*
C190.69023 (10)0.81129 (12)0.76936 (11)0.0444 (4)
C200.73405 (10)0.73593 (13)0.75407 (11)0.0479 (5)
H200.78140.74210.73120.057*
C210.70759 (9)0.65268 (12)0.77261 (11)0.0449 (4)
H210.73670.60200.76170.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0401 (6)0.0698 (9)0.0478 (8)0.0101 (6)0.0106 (6)0.0027 (6)
O20.0403 (6)0.0483 (7)0.0658 (8)0.0051 (6)0.0157 (6)0.0029 (6)
O30.0863 (10)0.0796 (11)0.0809 (11)0.0302 (8)0.0303 (9)0.0124 (8)
O40.0939 (11)0.0510 (9)0.0967 (12)0.0057 (8)0.0129 (9)0.0142 (8)
N10.0367 (7)0.0480 (9)0.0422 (8)0.0040 (6)0.0117 (7)0.0012 (7)
N20.0403 (7)0.0416 (8)0.0556 (9)0.0002 (6)0.0175 (7)0.0007 (7)
N30.0685 (11)0.0585 (12)0.0513 (10)0.0160 (10)0.0036 (9)0.0076 (8)
C10.0419 (9)0.0577 (12)0.0461 (11)0.0034 (9)0.0081 (9)0.0046 (9)
C20.0433 (10)0.0656 (13)0.0646 (13)0.0050 (9)0.0065 (10)0.0110 (10)
C30.0515 (11)0.0848 (16)0.0709 (15)0.0201 (11)0.0183 (11)0.0003 (12)
C40.0599 (12)0.1042 (18)0.0522 (13)0.0172 (12)0.0211 (11)0.0024 (12)
C50.0436 (10)0.0691 (13)0.0474 (11)0.0078 (9)0.0102 (9)0.0040 (9)
C60.0325 (8)0.0460 (10)0.0460 (10)0.0039 (7)0.0095 (8)0.0023 (8)
C70.0427 (10)0.0618 (12)0.0543 (12)0.0057 (9)0.0092 (9)0.0055 (10)
C80.0416 (10)0.0517 (11)0.0684 (13)0.0038 (8)0.0142 (9)0.0037 (10)
C90.0336 (8)0.0462 (11)0.0408 (10)0.0065 (8)0.0047 (8)0.0019 (8)
C100.0398 (9)0.0417 (11)0.0607 (12)0.0018 (8)0.0119 (9)0.0040 (9)
C110.0427 (10)0.0387 (10)0.0570 (11)0.0036 (8)0.0095 (9)0.0062 (8)
C120.0385 (9)0.0417 (10)0.0371 (9)0.0019 (8)0.0041 (8)0.0039 (7)
C130.0459 (9)0.0394 (10)0.0545 (11)0.0033 (8)0.0119 (9)0.0032 (8)
C140.0484 (10)0.0385 (10)0.0504 (11)0.0065 (8)0.0086 (9)0.0038 (8)
C150.0432 (9)0.0424 (10)0.0444 (10)0.0015 (8)0.0085 (8)0.0022 (8)
C160.0365 (8)0.0419 (10)0.0346 (9)0.0025 (8)0.0067 (7)0.0004 (8)
C170.0442 (9)0.0483 (11)0.0525 (11)0.0016 (8)0.0182 (9)0.0019 (9)
C180.0512 (10)0.0434 (11)0.0516 (11)0.0018 (8)0.0115 (9)0.0006 (9)
C190.0485 (10)0.0456 (11)0.0381 (10)0.0126 (9)0.0048 (8)0.0035 (8)
C200.0402 (9)0.0623 (13)0.0439 (10)0.0075 (9)0.0148 (8)0.0008 (9)
C210.0394 (9)0.0520 (11)0.0455 (10)0.0011 (8)0.0137 (8)0.0006 (8)
Geometric parameters (Å, º) top
O1—C61.3637 (18)C8—H8A0.9700
O1—C71.4234 (19)C8—H8B0.9700
O2—C91.3637 (17)C9—C141.383 (2)
O2—C81.426 (2)C9—C101.392 (2)
O3—N31.2402 (19)C10—C111.374 (2)
O4—N31.233 (2)C10—H100.9300
N1—C151.2745 (19)C11—C121.390 (2)
N1—N21.3612 (17)C11—H110.9300
N2—C161.361 (2)C12—C131.391 (2)
N2—H20.8600C12—C151.453 (2)
N3—C191.437 (2)C13—C141.378 (2)
C1—C21.373 (2)C13—H130.9300
C1—C61.382 (2)C14—H140.9300
C1—H10.9300C15—H150.9300
C2—C31.373 (3)C16—C211.398 (2)
C2—H2A0.9300C16—C171.399 (2)
C3—C41.372 (3)C17—C181.370 (2)
C3—H30.9300C17—H170.9300
C4—C51.375 (2)C18—C191.380 (2)
C4—H40.9300C18—H180.9300
C5—C61.376 (2)C19—C201.384 (2)
C5—H50.9300C20—C211.362 (2)
C7—C81.491 (2)C20—H200.9300
C7—H7A0.9700C21—H210.9300
C7—H7B0.9700
C6—O1—C7117.33 (12)O2—C9—C14116.36 (15)
C9—O2—C8117.30 (13)O2—C9—C10124.28 (15)
C15—N1—N2117.78 (14)C14—C9—C10119.36 (15)
C16—N2—N1119.73 (13)C11—C10—C9119.80 (16)
C16—N2—H2120.1C11—C10—H10120.1
N1—N2—H2120.1C9—C10—H10120.1
O4—N3—O3122.40 (17)C10—C11—C12121.84 (16)
O4—N3—C19118.93 (17)C10—C11—H11119.1
O3—N3—C19118.66 (18)C12—C11—H11119.1
C2—C1—C6120.15 (16)C11—C12—C13117.39 (15)
C2—C1—H1119.9C11—C12—C15121.17 (15)
C6—C1—H1119.9C13—C12—C15121.43 (15)
C1—C2—C3120.68 (18)C14—C13—C12121.54 (16)
C1—C2—H2A119.7C14—C13—H13119.2
C3—C2—H2A119.7C12—C13—H13119.2
C4—C3—C2118.59 (18)C13—C14—C9120.06 (16)
C4—C3—H3120.7C13—C14—H14120.0
C2—C3—H3120.7C9—C14—H14120.0
C3—C4—C5121.70 (18)N1—C15—C12120.66 (15)
C3—C4—H4119.2N1—C15—H15119.7
C5—C4—H4119.2C12—C15—H15119.7
C4—C5—C6119.19 (17)N2—C16—C21119.43 (15)
C4—C5—H5120.4N2—C16—C17121.58 (14)
C6—C5—H5120.4C21—C16—C17118.99 (16)
O1—C6—C5124.70 (15)C18—C17—C16120.40 (16)
O1—C6—C1115.65 (14)C18—C17—H17119.8
C5—C6—C1119.64 (16)C16—C17—H17119.8
O1—C7—C8109.20 (14)C17—C18—C19119.45 (17)
O1—C7—H7A109.8C17—C18—H18120.3
C8—C7—H7A109.8C19—C18—H18120.3
O1—C7—H7B109.8C18—C19—C20120.90 (16)
C8—C7—H7B109.8C18—C19—N3119.79 (17)
H7A—C7—H7B108.3C20—C19—N3119.30 (16)
O2—C8—C7108.43 (15)C21—C20—C19119.85 (15)
O2—C8—H8A110.0C21—C20—H20120.1
C7—C8—H8A110.0C19—C20—H20120.1
O2—C8—H8B110.0C20—C21—C16120.35 (16)
C7—C8—H8B110.0C20—C21—H21119.8
H8A—C8—H8B108.4C16—C21—H21119.8
C15—N1—N2—C16179.18 (14)C12—C13—C14—C90.2 (2)
C6—C1—C2—C30.2 (3)O2—C9—C14—C13179.56 (13)
C1—C2—C3—C41.9 (3)C10—C9—C14—C131.0 (2)
C2—C3—C4—C51.7 (3)N2—N1—C15—C12179.23 (12)
C3—C4—C5—C60.1 (3)C11—C12—C15—N11.5 (2)
C7—O1—C6—C54.6 (2)C13—C12—C15—N1177.59 (15)
C7—O1—C6—C1175.21 (14)N1—N2—C16—C21176.51 (13)
C4—C5—C6—O1178.02 (16)N1—N2—C16—C174.0 (2)
C4—C5—C6—C11.8 (3)N2—C16—C17—C18178.38 (15)
C2—C1—C6—O1178.20 (15)C21—C16—C17—C182.1 (2)
C2—C1—C6—C51.7 (3)C16—C17—C18—C190.3 (2)
C6—O1—C7—C8176.64 (13)C17—C18—C19—C202.1 (2)
C9—O2—C8—C7172.06 (13)C17—C18—C19—N3176.76 (15)
O1—C7—C8—O276.12 (17)O4—N3—C19—C180.2 (2)
C8—O2—C9—C14175.22 (14)O3—N3—C19—C18179.44 (15)
C8—O2—C9—C105.3 (2)O4—N3—C19—C20178.70 (16)
O2—C9—C10—C11179.30 (14)O3—N3—C19—C200.6 (2)
C14—C9—C10—C111.3 (2)C18—C19—C20—C212.6 (2)
C9—C10—C11—C120.9 (2)N3—C19—C20—C21176.23 (15)
C10—C11—C12—C130.1 (2)C19—C20—C21—C160.7 (2)
C10—C11—C12—C15179.25 (15)N2—C16—C21—C20178.90 (15)
C11—C12—C13—C140.2 (2)C17—C16—C21—C201.6 (2)
C15—C12—C13—C14178.93 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.862.233.087 (2)173
C21—H21···O4i0.932.563.485 (2)176
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

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