(E)-N′-(4-Benzo­yloxy-3-meth­oxybenzyl­idene)-2-meth­oxybenzohydrazide monohydrate

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.

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

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Computing details

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

Crystal data

C23H20N2O5·H2O	F(000) = 888
Mr = 422.43	Dx = 1.334 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1909 reflections
a = 7.9685 (15) Å	θ = 2.6–21.3°
b = 18.584 (3) Å	µ = 0.10 mm^−1
c = 14.205 (3) Å	T = 294 K
β = 91.045 (4)°	Block, pale yellow
V = 2103.2 (7) Å^3	0.22 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4281 independent reflections
Radiation source: fine-focus sealed tube	1915 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.963, Tmax = 0.981	k = −16→23
11792 measured reflections	l = −14→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
4281 reflections	(Δ/σ)max = 0.003
282 parameters	Δρmax = 0.19 e Å^−3
3 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9451 (2)	0.62028 (9)	−0.11615 (11)	0.0676 (5)
O2	0.71831 (19)	0.58742 (8)	−0.03682 (11)	0.0634 (5)
O3	0.6881 (2)	0.72976 (10)	−0.00990 (12)	0.0720 (5)
O4	1.1086 (3)	0.60543 (9)	0.52451 (12)	0.0923 (6)
O5	1.24028 (19)	0.81997 (8)	0.51866 (11)	0.0597 (5)
N1	1.0246 (2)	0.67207 (10)	0.36570 (14)	0.0538 (5)
N2	1.0955 (2)	0.70756 (9)	0.44153 (13)	0.0521 (5)
H2	1.1098	0.7534	0.4399	0.063*
C1	0.5699 (3)	0.52482 (11)	−0.19102 (17)	0.0534 (6)
H1	0.5155	0.5237	−0.1337	0.064*
C2	0.4957 (3)	0.49355 (12)	−0.2692 (2)	0.0663 (7)
H2A	0.3911	0.4717	−0.2649	0.080*
C3	0.5770 (4)	0.49477 (14)	−0.3534 (2)	0.0797 (9)
H3	0.5274	0.4735	−0.4062	0.096*
C4	0.7306 (4)	0.52714 (15)	−0.3603 (2)	0.0804 (9)
H4	0.7846	0.5280	−0.4178	0.097*
C5	0.8055 (3)	0.55848 (12)	−0.28242 (19)	0.0652 (7)
H5	0.9104	0.5800	−0.2873	0.078*
C6	0.7252 (3)	0.55808 (11)	−0.19724 (16)	0.0469 (6)
C7	0.8101 (3)	0.59216 (12)	−0.11557 (17)	0.0484 (6)
C8	0.7869 (3)	0.61894 (14)	0.04522 (17)	0.0537 (6)
C9	0.8634 (3)	0.57585 (13)	0.11126 (18)	0.0629 (7)
H9	0.8739	0.5268	0.1000	0.076*
C10	0.9252 (3)	0.60480 (13)	0.19456 (16)	0.0599 (7)
H10	0.9786	0.5756	0.2390	0.072*
C11	0.9065 (3)	0.67801 (13)	0.21114 (16)	0.0486 (6)
C12	0.8289 (3)	0.72149 (12)	0.14365 (17)	0.0529 (6)
H12	0.8183	0.7706	0.1546	0.063*
C13	0.7672 (3)	0.69232 (14)	0.06009 (17)	0.0530 (6)
C14	0.6622 (3)	0.80473 (14)	0.00435 (19)	0.0763 (8)
H14A	0.5972	0.8118	0.0598	0.114*
H14B	0.6032	0.8246	−0.0492	0.114*
H14C	0.7687	0.8283	0.0120	0.114*
C15	0.9742 (3)	0.71078 (12)	0.29746 (17)	0.0514 (6)
H15	0.9804	0.7606	0.3023	0.062*
C16	1.1425 (3)	0.66951 (13)	0.51857 (17)	0.0533 (6)
C17	1.2331 (3)	0.70788 (12)	0.59626 (16)	0.0460 (6)
C18	1.2756 (3)	0.66660 (13)	0.67498 (18)	0.0630 (7)
H18	1.2451	0.6183	0.6761	0.076*
C19	1.3609 (4)	0.69509 (17)	0.75086 (19)	0.0751 (8)
H19	1.3872	0.6666	0.8029	0.090*
C20	1.4072 (3)	0.76627 (18)	0.7491 (2)	0.0781 (8)
H20	1.4663	0.7858	0.8001	0.094*
C21	1.3673 (3)	0.80902 (13)	0.67302 (18)	0.0621 (7)
H21	1.3981	0.8573	0.6730	0.075*
C22	1.2817 (3)	0.78026 (12)	0.59672 (17)	0.0477 (6)
C23	1.2862 (3)	0.89352 (12)	0.51519 (17)	0.0684 (7)
H23A	1.2346	0.9189	0.5659	0.103*
H23B	1.2491	0.9138	0.4562	0.103*
H23C	1.4060	0.8978	0.5210	0.103*
O6	0.8341 (2)	0.53234 (9)	0.39921 (12)	0.0940 (6)
H6A	0.8514	0.4897	0.4223	0.113*
H6B	0.9123	0.5628	0.4133	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0579 (11)	0.0831 (12)	0.0620 (12)	−0.0204 (10)	0.0036 (9)	−0.0061 (9)
O2	0.0626 (11)	0.0805 (12)	0.0472 (11)	−0.0255 (9)	0.0068 (9)	−0.0224 (9)
O3	0.0794 (13)	0.0740 (13)	0.0618 (12)	0.0036 (10)	−0.0197 (10)	−0.0122 (10)
O4	0.1435 (18)	0.0444 (11)	0.0879 (15)	−0.0215 (11)	−0.0313 (13)	0.0092 (9)
O5	0.0751 (12)	0.0402 (10)	0.0630 (12)	−0.0089 (8)	−0.0208 (9)	0.0053 (8)
N1	0.0628 (13)	0.0517 (12)	0.0467 (13)	−0.0143 (10)	−0.0022 (11)	−0.0076 (11)
N2	0.0661 (14)	0.0431 (12)	0.0470 (13)	−0.0118 (10)	−0.0054 (11)	−0.0046 (10)
C1	0.0601 (17)	0.0525 (15)	0.0474 (16)	0.0013 (13)	−0.0073 (13)	−0.0042 (12)
C2	0.0721 (19)	0.0640 (17)	0.062 (2)	−0.0055 (14)	−0.0212 (16)	−0.0044 (14)
C3	0.111 (3)	0.075 (2)	0.052 (2)	0.0005 (18)	−0.0167 (19)	−0.0112 (14)
C4	0.104 (3)	0.091 (2)	0.0467 (19)	0.0029 (19)	0.0092 (18)	−0.0058 (16)
C5	0.0695 (18)	0.0720 (18)	0.0544 (18)	−0.0007 (14)	0.0062 (16)	−0.0047 (14)
C6	0.0553 (16)	0.0392 (14)	0.0459 (16)	0.0060 (11)	−0.0027 (13)	−0.0002 (11)
C7	0.0561 (17)	0.0431 (14)	0.0461 (16)	−0.0009 (12)	0.0019 (14)	−0.0025 (11)
C8	0.0553 (16)	0.0631 (18)	0.0428 (16)	−0.0206 (13)	0.0069 (13)	−0.0160 (14)
C9	0.083 (2)	0.0526 (16)	0.0532 (17)	−0.0174 (14)	0.0077 (15)	−0.0092 (14)
C10	0.0797 (19)	0.0509 (16)	0.0489 (16)	−0.0107 (13)	−0.0013 (14)	−0.0048 (13)
C11	0.0495 (15)	0.0526 (16)	0.0440 (16)	−0.0133 (12)	0.0051 (12)	−0.0073 (12)
C12	0.0524 (15)	0.0523 (15)	0.0541 (17)	−0.0094 (12)	0.0030 (13)	−0.0093 (13)
C13	0.0456 (15)	0.0662 (18)	0.0471 (16)	−0.0093 (12)	−0.0014 (13)	−0.0058 (14)
C14	0.0725 (19)	0.080 (2)	0.076 (2)	0.0103 (15)	−0.0145 (16)	−0.0015 (15)
C15	0.0531 (15)	0.0528 (16)	0.0483 (16)	−0.0106 (12)	0.0021 (13)	−0.0058 (13)
C16	0.0621 (16)	0.0440 (15)	0.0537 (17)	−0.0050 (13)	0.0004 (13)	−0.0004 (13)
C17	0.0441 (14)	0.0464 (15)	0.0475 (15)	0.0033 (11)	−0.0003 (12)	0.0012 (12)
C18	0.0696 (18)	0.0609 (17)	0.0584 (18)	0.0084 (13)	−0.0022 (15)	0.0088 (14)
C19	0.080 (2)	0.094 (2)	0.0509 (19)	0.0137 (17)	−0.0119 (16)	0.0120 (16)
C20	0.073 (2)	0.105 (2)	0.056 (2)	0.0017 (18)	−0.0189 (15)	−0.0116 (17)
C21	0.0611 (17)	0.0662 (17)	0.0586 (18)	−0.0026 (13)	−0.0120 (14)	−0.0076 (15)
C22	0.0432 (14)	0.0526 (16)	0.0471 (16)	0.0054 (12)	−0.0033 (12)	−0.0014 (13)
C23	0.0701 (18)	0.0485 (16)	0.086 (2)	−0.0123 (13)	−0.0112 (15)	0.0079 (13)
O6	0.1101 (15)	0.0776 (13)	0.0934 (15)	−0.0270 (11)	−0.0208 (12)	0.0167 (10)

Geometric parameters (Å, º)

O1—C7	1.197 (2)	C9—H9	0.9300
O2—C7	1.350 (2)	C10—C11	1.389 (3)
O2—C8	1.406 (3)	C10—H10	0.9300
O3—C13	1.359 (3)	C11—C12	1.390 (3)
O3—C14	1.423 (3)	C11—C15	1.463 (3)
O4—C16	1.224 (2)	C12—C13	1.387 (3)
O5—C22	1.367 (3)	C12—H12	0.9300
O5—C23	1.416 (2)	C14—H14A	0.9600
N1—C15	1.267 (3)	C14—H14B	0.9600
N1—N2	1.376 (2)	C14—H14C	0.9600
N2—C16	1.350 (3)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.490 (3)
C1—C2	1.377 (3)	C17—C18	1.393 (3)
C1—C6	1.388 (3)	C17—C22	1.400 (3)
C1—H1	0.9300	C18—C19	1.370 (3)
C2—C3	1.371 (4)	C18—H18	0.9300
C2—H2A	0.9300	C19—C20	1.374 (3)
C3—C4	1.369 (4)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.374 (3)
C4—C5	1.377 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.378 (3)
C5—C6	1.379 (3)	C21—H21	0.9300
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.475 (3)	C23—H23B	0.9600
C8—C9	1.368 (3)	C23—H23C	0.9600
C8—C13	1.389 (3)	O6—H6A	0.8682
C9—C10	1.382 (3)	O6—H6B	0.8626
C7—O2—C8	116.81 (17)	C11—C12—H12	119.7
C13—O3—C14	117.61 (19)	O3—C13—C12	125.3 (2)
C22—O5—C23	119.37 (18)	O3—C13—C8	116.3 (2)
C15—N1—N2	116.5 (2)	C12—C13—C8	118.3 (2)
C16—N2—N1	119.17 (19)	O3—C14—H14A	109.5
C16—N2—H2	120.4	O3—C14—H14B	109.5
N1—N2—H2	120.4	H14A—C14—H14B	109.5
C2—C1—C6	120.5 (2)	O3—C14—H14C	109.5
C2—C1—H1	119.8	H14A—C14—H14C	109.5
C6—C1—H1	119.8	H14B—C14—H14C	109.5
C3—C2—C1	119.6 (3)	N1—C15—C11	120.8 (2)
C3—C2—H2A	120.2	N1—C15—H15	119.6
C1—C2—H2A	120.2	C11—C15—H15	119.6
C2—C3—C4	120.5 (3)	O4—C16—N2	120.5 (2)
C2—C3—H3	119.8	O4—C16—C17	121.3 (2)
C4—C3—H3	119.8	N2—C16—C17	118.2 (2)
C3—C4—C5	120.2 (3)	C18—C17—C22	117.6 (2)
C3—C4—H4	119.9	C18—C17—C16	116.0 (2)
C5—C4—H4	119.9	C22—C17—C16	126.4 (2)
C4—C5—C6	120.1 (3)	C19—C18—C17	121.9 (2)
C4—C5—H5	119.9	C19—C18—H18	119.0
C6—C5—H5	119.9	C17—C18—H18	119.0
C5—C6—C1	119.1 (2)	C18—C19—C20	119.2 (2)
C5—C6—C7	118.3 (2)	C18—C19—H19	120.4
C1—C6—C7	122.5 (2)	C20—C19—H19	120.4
O1—C7—O2	122.3 (2)	C19—C20—C21	120.9 (3)
O1—C7—C6	125.6 (2)	C19—C20—H20	119.6
O2—C7—C6	112.1 (2)	C21—C20—H20	119.6
C9—C8—C13	121.4 (2)	C20—C21—C22	119.9 (3)
C9—C8—O2	119.1 (2)	C20—C21—H21	120.0
C13—C8—O2	119.5 (2)	C22—C21—H21	120.0
C8—C9—C10	120.4 (2)	O5—C22—C21	122.5 (2)
C8—C9—H9	119.8	O5—C22—C17	116.9 (2)
C10—C9—H9	119.8	C21—C22—C17	120.6 (2)
C9—C10—C11	119.3 (2)	O5—C23—H23A	109.5
C9—C10—H10	120.4	O5—C23—H23B	109.5
C11—C10—H10	120.4	H23A—C23—H23B	109.5
C10—C11—C12	120.0 (2)	O5—C23—H23C	109.5
C10—C11—C15	120.7 (2)	H23A—C23—H23C	109.5
C12—C11—C15	119.2 (2)	H23B—C23—H23C	109.5
C13—C12—C11	120.6 (2)	H6A—O6—H6B	113.7
C13—C12—H12	119.7
C15—N1—N2—C16	176.1 (2)	C11—C12—C13—C8	−0.8 (3)
C6—C1—C2—C3	0.6 (3)	C9—C8—C13—O3	−179.4 (2)
C1—C2—C3—C4	−0.3 (4)	O2—C8—C13—O3	−3.2 (3)
C2—C3—C4—C5	0.4 (4)	C9—C8—C13—C12	0.7 (3)
C3—C4—C5—C6	−0.7 (4)	O2—C8—C13—C12	176.91 (19)
C4—C5—C6—C1	1.0 (3)	N2—N1—C15—C11	176.18 (18)
C4—C5—C6—C7	179.9 (2)	C10—C11—C15—N1	−12.5 (3)
C2—C1—C6—C5	−0.9 (3)	C12—C11—C15—N1	170.2 (2)
C2—C1—C6—C7	−179.8 (2)	N1—N2—C16—O4	−6.6 (3)
C8—O2—C7—O1	1.6 (3)	N1—N2—C16—C17	174.48 (18)
C8—O2—C7—C6	−179.3 (2)	O4—C16—C17—C18	−0.2 (3)
C5—C6—C7—O1	−0.5 (3)	N2—C16—C17—C18	178.7 (2)
C1—C6—C7—O1	178.4 (2)	O4—C16—C17—C22	178.5 (2)
C5—C6—C7—O2	−179.53 (19)	N2—C16—C17—C22	−2.6 (3)
C1—C6—C7—O2	−0.6 (3)	C22—C17—C18—C19	0.3 (3)
C7—O2—C8—C9	−100.8 (3)	C16—C17—C18—C19	179.2 (2)
C7—O2—C8—C13	82.9 (3)	C17—C18—C19—C20	−0.5 (4)
C13—C8—C9—C10	−0.8 (4)	C18—C19—C20—C21	0.8 (4)
O2—C8—C9—C10	−177.0 (2)	C19—C20—C21—C22	−0.8 (4)
C8—C9—C10—C11	0.9 (4)	C23—O5—C22—C21	−0.1 (3)
C9—C10—C11—C12	−1.1 (3)	C23—O5—C22—C17	179.99 (19)
C9—C10—C11—C15	−178.4 (2)	C20—C21—C22—O5	−179.3 (2)
C10—C11—C12—C13	1.0 (3)	C20—C21—C22—C17	0.7 (4)
C15—C11—C12—C13	178.4 (2)	C18—C17—C22—O5	179.52 (19)
C14—O3—C13—C12	−1.7 (3)	C16—C17—C22—O5	0.8 (3)
C14—O3—C13—C8	178.4 (2)	C18—C17—C22—C21	−0.4 (3)
C11—C12—C13—O3	179.3 (2)	C16—C17—C22—C21	−179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.86	1.95	2.617 (2)	133
O6—H6A···O4^i	0.87	1.95	2.814 (2)	179
O6—H6B···N1	0.86	2.32	3.050 (2)	142
O6—H6B···O4	0.86	2.34	3.108 (3)	148
C15—H15···O1^ii	0.93	2.52	3.380 (3)	155

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.