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In the title compound, C23H22N2O6, the vanillin group makes dihedral angles of 81.15 (6) and 23.52 (7)°, respectively, with the phenyl ring and the benzohydrazide mean plane. An intra­molecular N—H...O hydrogen bond helps to stabilize the mol­ecular conformation, while the water mol­ecule inter­acts with the organic mol­ecule by way of a bifurcated O—H...(O,N) inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047519/hb2196sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047519/hb2196Isup2.hkl
Contains datablock I

CCDC reference: 629885

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
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 0 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)-2-Methoxy-N'-[(3-methoxy-4-benzoyloxy)benzylidene]benzohydrazide monohydrate top
Crystal data top
C23H20N2O5·H2OF(000) = 888
Mr = 422.43Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1909 reflections
a = 7.9685 (15) Åθ = 2.6–21.3°
b = 18.584 (3) ŵ = 0.10 mm1
c = 14.205 (3) ÅT = 294 K
β = 91.045 (4)°Block, pale yellow
V = 2103.2 (7) Å30.22 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4281 independent reflections
Radiation source: fine-focus sealed tube1915 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.963, Tmax = 0.981k = 1623
11792 measured reflectionsl = 1417
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
4281 reflections(Δ/σ)max = 0.003
282 parametersΔρmax = 0.19 e Å3
3 restraintsΔρmin = 0.18 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
O10.9451 (2)0.62028 (9)0.11615 (11)0.0676 (5)
O20.71831 (19)0.58742 (8)0.03682 (11)0.0634 (5)
O30.6881 (2)0.72976 (10)0.00990 (12)0.0720 (5)
O41.1086 (3)0.60543 (9)0.52451 (12)0.0923 (6)
O51.24028 (19)0.81997 (8)0.51866 (11)0.0597 (5)
N11.0246 (2)0.67207 (10)0.36570 (14)0.0538 (5)
N21.0955 (2)0.70756 (9)0.44153 (13)0.0521 (5)
H21.10980.75340.43990.063*
C10.5699 (3)0.52482 (11)0.19102 (17)0.0534 (6)
H10.51550.52370.13370.064*
C20.4957 (3)0.49355 (12)0.2692 (2)0.0663 (7)
H2A0.39110.47170.26490.080*
C30.5770 (4)0.49477 (14)0.3534 (2)0.0797 (9)
H30.52740.47350.40620.096*
C40.7306 (4)0.52714 (15)0.3603 (2)0.0804 (9)
H40.78460.52800.41780.097*
C50.8055 (3)0.55848 (12)0.28242 (19)0.0652 (7)
H50.91040.58000.28730.078*
C60.7252 (3)0.55808 (11)0.19724 (16)0.0469 (6)
C70.8101 (3)0.59216 (12)0.11557 (17)0.0484 (6)
C80.7869 (3)0.61894 (14)0.04522 (17)0.0537 (6)
C90.8634 (3)0.57585 (13)0.11126 (18)0.0629 (7)
H90.87390.52680.10000.076*
C100.9252 (3)0.60480 (13)0.19456 (16)0.0599 (7)
H100.97860.57560.23900.072*
C110.9065 (3)0.67801 (13)0.21114 (16)0.0486 (6)
C120.8289 (3)0.72149 (12)0.14365 (17)0.0529 (6)
H120.81830.77060.15460.063*
C130.7672 (3)0.69232 (14)0.06009 (17)0.0530 (6)
C140.6622 (3)0.80473 (14)0.00435 (19)0.0763 (8)
H14A0.59720.81180.05980.114*
H14B0.60320.82460.04920.114*
H14C0.76870.82830.01200.114*
C150.9742 (3)0.71078 (12)0.29746 (17)0.0514 (6)
H150.98040.76060.30230.062*
C161.1425 (3)0.66951 (13)0.51857 (17)0.0533 (6)
C171.2331 (3)0.70788 (12)0.59626 (16)0.0460 (6)
C181.2756 (3)0.66660 (13)0.67498 (18)0.0630 (7)
H181.24510.61830.67610.076*
C191.3609 (4)0.69509 (17)0.75086 (19)0.0751 (8)
H191.38720.66660.80290.090*
C201.4072 (3)0.76627 (18)0.7491 (2)0.0781 (8)
H201.46630.78580.80010.094*
C211.3673 (3)0.80902 (13)0.67302 (18)0.0621 (7)
H211.39810.85730.67300.075*
C221.2817 (3)0.78026 (12)0.59672 (17)0.0477 (6)
C231.2862 (3)0.89352 (12)0.51519 (17)0.0684 (7)
H23A1.23460.91890.56590.103*
H23B1.24910.91380.45620.103*
H23C1.40600.89780.52100.103*
O60.8341 (2)0.53234 (9)0.39921 (12)0.0940 (6)
H6A0.85140.48970.42230.113*
H6B0.91230.56280.41330.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0579 (11)0.0831 (12)0.0620 (12)0.0204 (10)0.0036 (9)0.0061 (9)
O20.0626 (11)0.0805 (12)0.0472 (11)0.0255 (9)0.0068 (9)0.0224 (9)
O30.0794 (13)0.0740 (13)0.0618 (12)0.0036 (10)0.0197 (10)0.0122 (10)
O40.1435 (18)0.0444 (11)0.0879 (15)0.0215 (11)0.0313 (13)0.0092 (9)
O50.0751 (12)0.0402 (10)0.0630 (12)0.0089 (8)0.0208 (9)0.0053 (8)
N10.0628 (13)0.0517 (12)0.0467 (13)0.0143 (10)0.0022 (11)0.0076 (11)
N20.0661 (14)0.0431 (12)0.0470 (13)0.0118 (10)0.0054 (11)0.0046 (10)
C10.0601 (17)0.0525 (15)0.0474 (16)0.0013 (13)0.0073 (13)0.0042 (12)
C20.0721 (19)0.0640 (17)0.062 (2)0.0055 (14)0.0212 (16)0.0044 (14)
C30.111 (3)0.075 (2)0.052 (2)0.0005 (18)0.0167 (19)0.0112 (14)
C40.104 (3)0.091 (2)0.0467 (19)0.0029 (19)0.0092 (18)0.0058 (16)
C50.0695 (18)0.0720 (18)0.0544 (18)0.0007 (14)0.0062 (16)0.0047 (14)
C60.0553 (16)0.0392 (14)0.0459 (16)0.0060 (11)0.0027 (13)0.0002 (11)
C70.0561 (17)0.0431 (14)0.0461 (16)0.0009 (12)0.0019 (14)0.0025 (11)
C80.0553 (16)0.0631 (18)0.0428 (16)0.0206 (13)0.0069 (13)0.0160 (14)
C90.083 (2)0.0526 (16)0.0532 (17)0.0174 (14)0.0077 (15)0.0092 (14)
C100.0797 (19)0.0509 (16)0.0489 (16)0.0107 (13)0.0013 (14)0.0048 (13)
C110.0495 (15)0.0526 (16)0.0440 (16)0.0133 (12)0.0051 (12)0.0073 (12)
C120.0524 (15)0.0523 (15)0.0541 (17)0.0094 (12)0.0030 (13)0.0093 (13)
C130.0456 (15)0.0662 (18)0.0471 (16)0.0093 (12)0.0014 (13)0.0058 (14)
C140.0725 (19)0.080 (2)0.076 (2)0.0103 (15)0.0145 (16)0.0015 (15)
C150.0531 (15)0.0528 (16)0.0483 (16)0.0106 (12)0.0021 (13)0.0058 (13)
C160.0621 (16)0.0440 (15)0.0537 (17)0.0050 (13)0.0004 (13)0.0004 (13)
C170.0441 (14)0.0464 (15)0.0475 (15)0.0033 (11)0.0003 (12)0.0012 (12)
C180.0696 (18)0.0609 (17)0.0584 (18)0.0084 (13)0.0022 (15)0.0088 (14)
C190.080 (2)0.094 (2)0.0509 (19)0.0137 (17)0.0119 (16)0.0120 (16)
C200.073 (2)0.105 (2)0.056 (2)0.0017 (18)0.0189 (15)0.0116 (17)
C210.0611 (17)0.0662 (17)0.0586 (18)0.0026 (13)0.0120 (14)0.0076 (15)
C220.0432 (14)0.0526 (16)0.0471 (16)0.0054 (12)0.0033 (12)0.0014 (13)
C230.0701 (18)0.0485 (16)0.086 (2)0.0123 (13)0.0112 (15)0.0079 (13)
O60.1101 (15)0.0776 (13)0.0934 (15)0.0270 (11)0.0208 (12)0.0167 (10)
Geometric parameters (Å, º) top
O1—C71.197 (2)C9—H90.9300
O2—C71.350 (2)C10—C111.389 (3)
O2—C81.406 (3)C10—H100.9300
O3—C131.359 (3)C11—C121.390 (3)
O3—C141.423 (3)C11—C151.463 (3)
O4—C161.224 (2)C12—C131.387 (3)
O5—C221.367 (3)C12—H120.9300
O5—C231.416 (2)C14—H14A0.9600
N1—C151.267 (3)C14—H14B0.9600
N1—N21.376 (2)C14—H14C0.9600
N2—C161.350 (3)C15—H150.9300
N2—H20.8600C16—C171.490 (3)
C1—C21.377 (3)C17—C181.393 (3)
C1—C61.388 (3)C17—C221.400 (3)
C1—H10.9300C18—C191.370 (3)
C2—C31.371 (4)C18—H180.9300
C2—H2A0.9300C19—C201.374 (3)
C3—C41.369 (4)C19—H190.9300
C3—H30.9300C20—C211.374 (3)
C4—C51.377 (3)C20—H200.9300
C4—H40.9300C21—C221.378 (3)
C5—C61.379 (3)C21—H210.9300
C5—H50.9300C23—H23A0.9600
C6—C71.475 (3)C23—H23B0.9600
C8—C91.368 (3)C23—H23C0.9600
C8—C131.389 (3)O6—H6A0.8682
C9—C101.382 (3)O6—H6B0.8626
C7—O2—C8116.81 (17)C11—C12—H12119.7
C13—O3—C14117.61 (19)O3—C13—C12125.3 (2)
C22—O5—C23119.37 (18)O3—C13—C8116.3 (2)
C15—N1—N2116.5 (2)C12—C13—C8118.3 (2)
C16—N2—N1119.17 (19)O3—C14—H14A109.5
C16—N2—H2120.4O3—C14—H14B109.5
N1—N2—H2120.4H14A—C14—H14B109.5
C2—C1—C6120.5 (2)O3—C14—H14C109.5
C2—C1—H1119.8H14A—C14—H14C109.5
C6—C1—H1119.8H14B—C14—H14C109.5
C3—C2—C1119.6 (3)N1—C15—C11120.8 (2)
C3—C2—H2A120.2N1—C15—H15119.6
C1—C2—H2A120.2C11—C15—H15119.6
C2—C3—C4120.5 (3)O4—C16—N2120.5 (2)
C2—C3—H3119.8O4—C16—C17121.3 (2)
C4—C3—H3119.8N2—C16—C17118.2 (2)
C3—C4—C5120.2 (3)C18—C17—C22117.6 (2)
C3—C4—H4119.9C18—C17—C16116.0 (2)
C5—C4—H4119.9C22—C17—C16126.4 (2)
C4—C5—C6120.1 (3)C19—C18—C17121.9 (2)
C4—C5—H5119.9C19—C18—H18119.0
C6—C5—H5119.9C17—C18—H18119.0
C5—C6—C1119.1 (2)C18—C19—C20119.2 (2)
C5—C6—C7118.3 (2)C18—C19—H19120.4
C1—C6—C7122.5 (2)C20—C19—H19120.4
O1—C7—O2122.3 (2)C19—C20—C21120.9 (3)
O1—C7—C6125.6 (2)C19—C20—H20119.6
O2—C7—C6112.1 (2)C21—C20—H20119.6
C9—C8—C13121.4 (2)C20—C21—C22119.9 (3)
C9—C8—O2119.1 (2)C20—C21—H21120.0
C13—C8—O2119.5 (2)C22—C21—H21120.0
C8—C9—C10120.4 (2)O5—C22—C21122.5 (2)
C8—C9—H9119.8O5—C22—C17116.9 (2)
C10—C9—H9119.8C21—C22—C17120.6 (2)
C9—C10—C11119.3 (2)O5—C23—H23A109.5
C9—C10—H10120.4O5—C23—H23B109.5
C11—C10—H10120.4H23A—C23—H23B109.5
C10—C11—C12120.0 (2)O5—C23—H23C109.5
C10—C11—C15120.7 (2)H23A—C23—H23C109.5
C12—C11—C15119.2 (2)H23B—C23—H23C109.5
C13—C12—C11120.6 (2)H6A—O6—H6B113.7
C13—C12—H12119.7
C15—N1—N2—C16176.1 (2)C11—C12—C13—C80.8 (3)
C6—C1—C2—C30.6 (3)C9—C8—C13—O3179.4 (2)
C1—C2—C3—C40.3 (4)O2—C8—C13—O33.2 (3)
C2—C3—C4—C50.4 (4)C9—C8—C13—C120.7 (3)
C3—C4—C5—C60.7 (4)O2—C8—C13—C12176.91 (19)
C4—C5—C6—C11.0 (3)N2—N1—C15—C11176.18 (18)
C4—C5—C6—C7179.9 (2)C10—C11—C15—N112.5 (3)
C2—C1—C6—C50.9 (3)C12—C11—C15—N1170.2 (2)
C2—C1—C6—C7179.8 (2)N1—N2—C16—O46.6 (3)
C8—O2—C7—O11.6 (3)N1—N2—C16—C17174.48 (18)
C8—O2—C7—C6179.3 (2)O4—C16—C17—C180.2 (3)
C5—C6—C7—O10.5 (3)N2—C16—C17—C18178.7 (2)
C1—C6—C7—O1178.4 (2)O4—C16—C17—C22178.5 (2)
C5—C6—C7—O2179.53 (19)N2—C16—C17—C222.6 (3)
C1—C6—C7—O20.6 (3)C22—C17—C18—C190.3 (3)
C7—O2—C8—C9100.8 (3)C16—C17—C18—C19179.2 (2)
C7—O2—C8—C1382.9 (3)C17—C18—C19—C200.5 (4)
C13—C8—C9—C100.8 (4)C18—C19—C20—C210.8 (4)
O2—C8—C9—C10177.0 (2)C19—C20—C21—C220.8 (4)
C8—C9—C10—C110.9 (4)C23—O5—C22—C210.1 (3)
C9—C10—C11—C121.1 (3)C23—O5—C22—C17179.99 (19)
C9—C10—C11—C15178.4 (2)C20—C21—C22—O5179.3 (2)
C10—C11—C12—C131.0 (3)C20—C21—C22—C170.7 (4)
C15—C11—C12—C13178.4 (2)C18—C17—C22—O5179.52 (19)
C14—O3—C13—C121.7 (3)C16—C17—C22—O50.8 (3)
C14—O3—C13—C8178.4 (2)C18—C17—C22—C210.4 (3)
C11—C12—C13—O3179.3 (2)C16—C17—C22—C21179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O50.861.952.617 (2)133
O6—H6A···O4i0.871.952.814 (2)179
O6—H6B···N10.862.323.050 (2)142
O6—H6B···O40.862.343.108 (3)148
C15—H15···O1ii0.932.523.380 (3)155
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+3/2, z+1/2.
 

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