(E)-N′-(4-Benz­yloxy-3-methoxy­benzyl­idene)benzohydrazide

The title compound, C₂₂H₂₀N₂O₃, was prepared by the reaction of 4-benz­yloxy-3-methoxy­benzaldehyde and benzohydrazide. The central vanillin system makes dihedral angles of 18.2 (1) and 14.3 (1)° with the planes of the benzohydrazide and benzyl groups, respectively. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.130
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 279
               Refinement of F2^ against ALL reflections.  The
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 282
               goodness of fit S are based on F2^, conventional
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 284
               on F, with F set to zero for negative F2^. The
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 291
               on F2^ are statistically about twice as large as
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   4 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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)—N'-(4-Benzyloxy-3-methoxybenzylidene)benzohydrazide

Crystal data

C22H20N2O3	F(000) = 760
Mr = 360.40	Dx = 1.289 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 1673 reflections
a = 7.528 (3) Å	θ = 2.6–23.1°
b = 25.027 (10) Å	µ = 0.09 mm^−1
c = 9.938 (4) Å	T = 293 K
β = 97.293 (8)°	Block, colorless
V = 1857.3 (13) Å^3	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3225 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.968, Tmax = 0.983	k = −26→29
8409 measured reflections	l = −10→11

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) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.062P)^2] where P = (Fo^2 + 2Fc^2)/3
3225 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.26 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	0.3466 (2)	0.54945 (6)	0.14849 (14)	0.0513 (5)
O2	0.3670 (2)	0.47361 (6)	0.32319 (14)	0.0554 (5)
O3	−0.0202 (2)	0.22775 (6)	0.20000 (14)	0.0547 (5)
N1	0.0925 (3)	0.30887 (7)	0.05521 (16)	0.0402 (5)
N2	0.0402 (3)	0.26011 (7)	−0.00160 (17)	0.0392 (5)
C1	0.3451 (3)	0.59250 (8)	0.0542 (2)	0.0457 (6)
H1A	0.2236	0.5987	0.0115	0.055*
H1B	0.4180	0.5833	−0.0162	0.055*
C2	0.4168 (3)	0.64225 (9)	0.1259 (2)	0.0409 (6)
C3	0.3906 (4)	0.69061 (10)	0.0610 (3)	0.0562 (7)
H3	0.3269	0.6922	−0.0254	0.067*
C4	0.4583 (4)	0.73694 (10)	0.1235 (3)	0.0710 (9)
H4	0.4411	0.7694	0.0783	0.085*
C5	0.5499 (4)	0.73543 (11)	0.2505 (3)	0.0720 (9)
H5	0.5933	0.7668	0.2928	0.086*
C6	0.5780 (4)	0.68734 (12)	0.3158 (3)	0.0690 (8)
H6	0.6425	0.6860	0.4019	0.083*
C7	0.5110 (4)	0.64087 (10)	0.2544 (2)	0.0559 (7)
H7	0.5293	0.6085	0.2998	0.067*
C8	0.2945 (3)	0.50057 (9)	0.0978 (2)	0.0402 (6)
C9	0.3031 (3)	0.45892 (9)	0.1932 (2)	0.0395 (6)
C10	0.2502 (3)	0.40855 (9)	0.1524 (2)	0.0409 (6)
H10	0.2553	0.3812	0.2161	0.049*
C11	0.1884 (3)	0.39742 (9)	0.0159 (2)	0.0386 (6)
C12	0.1846 (3)	0.43845 (9)	−0.0760 (2)	0.0489 (7)
H12	0.1470	0.4316	−0.1672	0.059*
C13	0.2357 (3)	0.48985 (9)	−0.0362 (2)	0.0491 (7)
H13	0.2302	0.5171	−0.1002	0.059*
C14	0.3678 (4)	0.43402 (10)	0.4267 (2)	0.0667 (8)
H14A	0.2478	0.4216	0.4302	0.100*
H14B	0.4141	0.4493	0.5127	0.100*
H14C	0.4420	0.4046	0.4068	0.100*
C15	0.1306 (3)	0.34418 (8)	−0.0287 (2)	0.0418 (6)
H15	0.1212	0.3358	−0.1204	0.050*
C16	−0.0154 (3)	0.22130 (9)	0.0783 (2)	0.0376 (6)
C17	−0.0667 (3)	0.16900 (8)	0.01121 (19)	0.0356 (6)
C18	−0.1099 (3)	0.12781 (10)	0.0931 (2)	0.0521 (7)
H18	−0.1087	0.1339	0.1856	0.063*
C19	−0.1548 (4)	0.07793 (11)	0.0413 (3)	0.0671 (8)
H19	−0.1821	0.0504	0.0982	0.081*
C20	−0.1588 (4)	0.06924 (11)	−0.0953 (3)	0.0660 (8)
H20	−0.1890	0.0357	−0.1315	0.079*
C21	−0.1186 (4)	0.10962 (10)	−0.1778 (2)	0.0622 (8)
H21	−0.1225	0.1035	−0.2704	0.075*
C22	−0.0723 (3)	0.15948 (9)	−0.1263 (2)	0.0514 (7)
H22	−0.0449	0.1867	−0.1839	0.062*
H2A	0.038 (3)	0.2554 (8)	−0.0910 (10)	0.041 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0812 (13)	0.0332 (10)	0.0386 (9)	−0.0067 (9)	0.0034 (8)	0.0006 (8)
O2	0.0896 (14)	0.0400 (10)	0.0334 (9)	−0.0050 (9)	−0.0046 (8)	−0.0008 (8)
O3	0.0900 (14)	0.0500 (11)	0.0254 (8)	−0.0053 (9)	0.0125 (8)	−0.0038 (7)
N1	0.0552 (14)	0.0306 (11)	0.0338 (10)	−0.0017 (9)	0.0020 (9)	−0.0044 (9)
N2	0.0604 (14)	0.0335 (12)	0.0234 (10)	−0.0030 (9)	0.0046 (9)	−0.0024 (9)
C1	0.0579 (18)	0.0373 (14)	0.0415 (13)	−0.0014 (12)	0.0045 (12)	0.0048 (11)
C2	0.0426 (16)	0.0361 (14)	0.0451 (14)	−0.0017 (11)	0.0093 (12)	−0.0012 (11)
C3	0.062 (2)	0.0407 (16)	0.0638 (16)	0.0004 (13)	0.0012 (14)	0.0027 (13)
C4	0.076 (2)	0.0380 (17)	0.098 (2)	−0.0013 (15)	0.0070 (19)	0.0036 (16)
C5	0.076 (2)	0.0502 (19)	0.088 (2)	−0.0116 (16)	0.0055 (18)	−0.0202 (17)
C6	0.076 (2)	0.068 (2)	0.0598 (17)	−0.0156 (17)	−0.0039 (15)	−0.0140 (16)
C7	0.070 (2)	0.0476 (16)	0.0490 (15)	−0.0097 (14)	0.0024 (14)	0.0003 (13)
C8	0.0529 (17)	0.0298 (13)	0.0385 (13)	−0.0020 (11)	0.0076 (12)	−0.0033 (11)
C9	0.0493 (16)	0.0376 (14)	0.0310 (12)	0.0025 (11)	0.0031 (11)	−0.0012 (10)
C10	0.0519 (17)	0.0356 (14)	0.0354 (13)	0.0013 (11)	0.0059 (11)	0.0036 (11)
C11	0.0487 (16)	0.0340 (13)	0.0335 (12)	0.0001 (11)	0.0072 (11)	−0.0011 (11)
C12	0.071 (2)	0.0426 (15)	0.0314 (12)	−0.0052 (13)	0.0004 (12)	−0.0025 (12)
C13	0.074 (2)	0.0365 (15)	0.0354 (13)	−0.0031 (13)	0.0037 (13)	0.0065 (11)
C14	0.095 (2)	0.0633 (19)	0.0372 (14)	−0.0081 (16)	−0.0101 (14)	0.0091 (13)
C15	0.0566 (18)	0.0368 (14)	0.0320 (12)	−0.0013 (12)	0.0055 (12)	−0.0016 (11)
C16	0.0494 (16)	0.0369 (14)	0.0260 (12)	0.0021 (11)	0.0028 (11)	0.0000 (10)
C17	0.0407 (15)	0.0384 (14)	0.0272 (11)	−0.0011 (11)	0.0020 (10)	0.0008 (10)
C18	0.068 (2)	0.0520 (17)	0.0373 (13)	−0.0162 (14)	0.0098 (12)	0.0010 (12)
C19	0.094 (2)	0.0534 (18)	0.0548 (17)	−0.0303 (16)	0.0123 (16)	0.0058 (14)
C20	0.089 (2)	0.0493 (17)	0.0600 (17)	−0.0265 (15)	0.0093 (16)	−0.0109 (14)
C21	0.092 (2)	0.0582 (18)	0.0377 (14)	−0.0204 (16)	0.0124 (14)	−0.0117 (13)
C22	0.081 (2)	0.0404 (15)	0.0340 (13)	−0.0071 (13)	0.0119 (13)	−0.0002 (11)

Geometric parameters (Å, º)

O1—C8	1.362 (3)	C9—C10	1.368 (3)
O1—C1	1.427 (2)	C10—C11	1.405 (3)
O2—C9	1.370 (2)	C10—H10	0.9300
O2—C14	1.428 (3)	C11—C12	1.372 (3)
O3—C16	1.225 (2)	C11—C15	1.453 (3)
N1—C15	1.272 (2)	C12—C13	1.386 (3)
N1—N2	1.381 (2)	C12—H12	0.9300
N2—C16	1.354 (3)	C13—H13	0.9300
N2—H2A	0.894 (9)	C14—H14A	0.9600
C1—C2	1.501 (3)	C14—H14B	0.9600
C1—H1A	0.9700	C14—H14C	0.9600
C1—H1B	0.9700	C15—H15	0.9300
C2—C3	1.374 (3)	C16—C17	1.497 (3)
C2—C7	1.380 (3)	C17—C18	1.378 (3)
C3—C4	1.382 (3)	C17—C22	1.383 (3)
C3—H3	0.9300	C18—C19	1.376 (3)
C4—C5	1.360 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.372 (3)
C5—C6	1.371 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.359 (3)
C6—C7	1.379 (3)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.377 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C13	1.375 (3)	C22—H22	0.9300
C8—C9	1.405 (3)
C8—O1—C1	117.20 (16)	C12—C11—C10	118.1 (2)
C9—O2—C14	117.50 (17)	C12—C11—C15	120.2 (2)
C15—N1—N2	114.98 (17)	C10—C11—C15	121.7 (2)
C16—N2—N1	119.18 (17)	C11—C12—C13	121.5 (2)
C16—N2—H2A	121.3 (13)	C11—C12—H12	119.2
N1—N2—H2A	119.4 (13)	C13—C12—H12	119.2
O1—C1—C2	109.97 (18)	C8—C13—C12	120.1 (2)
O1—C1—H1A	109.7	C8—C13—H13	120.0
C2—C1—H1A	109.7	C12—C13—H13	120.0
O1—C1—H1B	109.7	O2—C14—H14A	109.5
C2—C1—H1B	109.7	O2—C14—H14B	109.5
H1A—C1—H1B	108.2	H14A—C14—H14B	109.5
C3—C2—C7	118.9 (2)	O2—C14—H14C	109.5
C3—C2—C1	119.1 (2)	H14A—C14—H14C	109.5
C7—C2—C1	122.0 (2)	H14B—C14—H14C	109.5
C2—C3—C4	120.4 (3)	N1—C15—C11	121.38 (19)
C2—C3—H3	119.8	N1—C15—H15	119.3
C4—C3—H3	119.8	C11—C15—H15	119.3
C5—C4—C3	120.6 (3)	O3—C16—N2	122.3 (2)
C5—C4—H4	119.7	O3—C16—C17	121.1 (2)
C3—C4—H4	119.7	N2—C16—C17	116.58 (17)
C4—C5—C6	119.5 (3)	C18—C17—C22	118.4 (2)
C4—C5—H5	120.2	C18—C17—C16	117.25 (19)
C6—C5—H5	120.2	C22—C17—C16	124.4 (2)
C5—C6—C7	120.4 (3)	C19—C18—C17	121.5 (2)
C5—C6—H6	119.8	C19—C18—H18	119.2
C7—C6—H6	119.8	C17—C18—H18	119.2
C6—C7—C2	120.3 (3)	C20—C19—C18	119.2 (2)
C6—C7—H7	119.9	C20—C19—H19	120.4
C2—C7—H7	119.9	C18—C19—H19	120.4
O1—C8—C13	125.1 (2)	C21—C20—C19	120.0 (2)
O1—C8—C9	115.47 (19)	C21—C20—H20	120.0
C13—C8—C9	119.4 (2)	C19—C20—H20	120.0
C10—C9—O2	125.53 (19)	C20—C21—C22	121.0 (2)
C10—C9—C8	119.8 (2)	C20—C21—H21	119.5
O2—C9—C8	114.70 (19)	C22—C21—H21	119.5
C9—C10—C11	121.2 (2)	C21—C22—C17	119.9 (2)
C9—C10—H10	119.4	C21—C22—H22	120.1
C11—C10—H10	119.4	C17—C22—H22	120.1
C15—N1—N2—C16	−175.2 (2)	C9—C10—C11—C15	−179.5 (2)
C8—O1—C1—C2	−176.45 (19)	C10—C11—C12—C13	−1.6 (4)
O1—C1—C2—C3	−165.7 (2)	C15—C11—C12—C13	178.8 (2)
O1—C1—C2—C7	15.3 (3)	O1—C8—C13—C12	−179.5 (2)
C7—C2—C3—C4	0.3 (4)	C9—C8—C13—C12	0.3 (4)
C1—C2—C3—C4	−178.7 (2)	C11—C12—C13—C8	1.0 (4)
C2—C3—C4—C5	−0.8 (4)	N2—N1—C15—C11	−179.8 (2)
C3—C4—C5—C6	1.2 (5)	C12—C11—C15—N1	−163.3 (2)
C4—C5—C6—C7	−1.2 (5)	C10—C11—C15—N1	17.1 (4)
C5—C6—C7—C2	0.8 (4)	N1—N2—C16—O3	−0.4 (3)
C3—C2—C7—C6	−0.3 (4)	N1—N2—C16—C17	−178.79 (18)
C1—C2—C7—C6	178.6 (2)	O3—C16—C17—C18	−3.4 (3)
C1—O1—C8—C13	−2.1 (3)	N2—C16—C17—C18	175.0 (2)
C1—O1—C8—C9	178.13 (19)	O3—C16—C17—C22	177.0 (2)
C14—O2—C9—C10	−4.4 (3)	N2—C16—C17—C22	−4.6 (3)
C14—O2—C9—C8	175.9 (2)	C22—C17—C18—C19	1.1 (4)
O1—C8—C9—C10	178.7 (2)	C16—C17—C18—C19	−178.5 (2)
C13—C8—C9—C10	−1.1 (3)	C17—C18—C19—C20	−0.8 (4)
O1—C8—C9—O2	−1.5 (3)	C18—C19—C20—C21	0.0 (5)
C13—C8—C9—O2	178.7 (2)	C19—C20—C21—C22	0.5 (5)
O2—C9—C10—C11	−179.2 (2)	C20—C21—C22—C17	−0.2 (4)
C8—C9—C10—C11	0.5 (3)	C18—C17—C22—C21	−0.6 (4)
C9—C10—C11—C12	0.9 (3)	C16—C17—C22—C21	179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3^i	0.89 (1)	2.11 (1)	2.958 (2)	158 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.