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

The title compound, C₂₁H₁₉N₃O₃, was prepared by the reaction of 4-benz­yloxy-3-methoxy­benzaldehyde and isonicotinohydrazide. The vanillin group makes dihedral angles of 27.88 (7) and 58.94 (6)° with the planes of the pyridine and phenyl rings, respectively. A weak inter­molecular C—H...N hydrogen bond helps to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.118
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ?

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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

Crystal data

C21H19N3O3	F(000) = 1520
Mr = 361.39	Dx = 1.304 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3439 reflections
a = 11.0418 (17) Å	θ = 2.7–25.5°
b = 8.0714 (12) Å	µ = 0.09 mm^−1
c = 41.313 (7) Å	T = 294 K
V = 3682.0 (10) Å^3	Block, colorless
Z = 8	0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3765 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.968, Tmax = 0.991	k = −6→10
19513 measured reflections	l = −42→51

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) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.519P] where P = (Fo^2 + 2Fc^2)/3
3765 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.15 e Å^−3
0 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	1.19420 (11)	0.17736 (15)	0.33724 (3)	0.0486 (4)
O2	0.98144 (12)	0.04956 (16)	0.34109 (3)	0.0542 (4)
O3	0.50933 (12)	0.35721 (17)	0.42609 (4)	0.0579 (4)
N1	0.75067 (14)	0.41523 (18)	0.42356 (4)	0.0396 (4)
N2	0.67070 (12)	0.51185 (18)	0.44105 (4)	0.0402 (4)
H2	0.6969	0.5936	0.4524	0.048*
N3	0.30919 (16)	0.7984 (2)	0.49178 (5)	0.0607 (5)
C1	1.3091 (2)	0.1713 (3)	0.27275 (6)	0.0676 (7)
H1	1.2361	0.2272	0.2703	0.081*
C2	1.3611 (3)	0.0939 (4)	0.24652 (7)	0.0878 (9)
H2A	1.3232	0.0987	0.2264	0.105*
C3	1.4677 (3)	0.0101 (4)	0.24971 (9)	0.0967 (10)
H3	1.5026	−0.0415	0.2319	0.116*
C4	1.5230 (2)	0.0025 (4)	0.27923 (8)	0.0913 (9)
H4	1.5953	−0.0555	0.2816	0.110*
C5	1.4717 (2)	0.0809 (3)	0.30577 (6)	0.0644 (6)
H5	1.5099	0.0755	0.3258	0.077*
C6	1.36452 (18)	0.1668 (2)	0.30270 (6)	0.0502 (5)
C7	1.30916 (17)	0.2550 (3)	0.33095 (5)	0.0520 (6)
H7A	1.3613	0.2462	0.3498	0.062*
H7B	1.2979	0.3714	0.3259	0.062*
C8	1.11858 (16)	0.2524 (2)	0.35860 (4)	0.0383 (4)
C9	1.14817 (17)	0.3875 (2)	0.37738 (5)	0.0431 (5)
H9	1.2264	0.4300	0.3769	0.052*
C10	1.06095 (16)	0.4607 (2)	0.39716 (5)	0.0416 (5)
H10	1.0810	0.5535	0.4094	0.050*
C11	0.94535 (16)	0.3970 (2)	0.39879 (4)	0.0358 (4)
C12	0.91625 (15)	0.2566 (2)	0.38038 (4)	0.0363 (4)
H12	0.8388	0.2118	0.3816	0.044*
C13	1.00123 (16)	0.1844 (2)	0.36050 (4)	0.0380 (4)
C14	0.8686 (2)	−0.0322 (3)	0.34394 (6)	0.0666 (7)
H14A	0.8587	−0.0719	0.3657	0.100*
H14B	0.8660	−0.1240	0.3292	0.100*
H14C	0.8044	0.0438	0.3389	0.100*
C15	0.85469 (16)	0.4800 (2)	0.41856 (4)	0.0375 (4)
H15	0.8728	0.5822	0.4277	0.045*
C16	0.55118 (16)	0.4771 (2)	0.44019 (4)	0.0371 (4)
C17	0.47135 (15)	0.5963 (2)	0.45773 (4)	0.0347 (4)
C18	0.50984 (17)	0.6995 (2)	0.48229 (5)	0.0434 (5)
H18	0.5913	0.7042	0.4879	0.052*
C19	0.42617 (19)	0.7956 (2)	0.49842 (5)	0.0505 (5)
H19	0.4539	0.8629	0.5151	0.061*
C20	0.27424 (19)	0.7032 (3)	0.46725 (6)	0.0650 (7)
H20	0.1930	0.7061	0.4613	0.078*
C21	0.35030 (17)	0.6002 (3)	0.44995 (5)	0.0512 (5)
H21	0.3201	0.5345	0.4333	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0443 (8)	0.0371 (8)	0.0646 (9)	−0.0021 (6)	0.0237 (7)	−0.0083 (7)
O2	0.0523 (9)	0.0485 (9)	0.0617 (9)	−0.0113 (7)	0.0192 (7)	−0.0227 (7)
O3	0.0480 (8)	0.0501 (9)	0.0758 (10)	−0.0069 (7)	0.0061 (7)	−0.0269 (8)
N1	0.0385 (9)	0.0358 (9)	0.0446 (9)	0.0051 (7)	0.0074 (7)	−0.0081 (7)
N2	0.0340 (8)	0.0382 (9)	0.0484 (10)	0.0031 (7)	0.0068 (7)	−0.0161 (7)
N3	0.0459 (11)	0.0600 (13)	0.0764 (14)	0.0085 (9)	0.0094 (9)	−0.0165 (10)
C1	0.0631 (15)	0.0665 (17)	0.0733 (18)	0.0036 (12)	0.0138 (13)	−0.0011 (13)
C2	0.098 (2)	0.101 (2)	0.0650 (18)	−0.0074 (19)	0.0188 (16)	−0.0151 (16)
C3	0.091 (2)	0.102 (2)	0.097 (2)	−0.0036 (19)	0.0430 (19)	−0.0352 (19)
C4	0.0690 (18)	0.088 (2)	0.117 (3)	0.0160 (15)	0.0329 (18)	−0.0261 (19)
C5	0.0547 (14)	0.0619 (15)	0.0765 (16)	0.0046 (12)	0.0185 (12)	−0.0065 (13)
C6	0.0469 (12)	0.0379 (12)	0.0659 (15)	−0.0037 (10)	0.0229 (11)	0.0001 (10)
C7	0.0466 (12)	0.0409 (12)	0.0684 (15)	−0.0028 (10)	0.0241 (11)	−0.0034 (11)
C8	0.0377 (10)	0.0326 (10)	0.0446 (11)	0.0054 (8)	0.0123 (9)	0.0003 (9)
C9	0.0360 (10)	0.0415 (12)	0.0519 (12)	−0.0028 (9)	0.0072 (9)	−0.0033 (10)
C10	0.0418 (11)	0.0396 (11)	0.0435 (11)	−0.0004 (9)	0.0038 (9)	−0.0081 (9)
C11	0.0371 (10)	0.0356 (10)	0.0347 (10)	0.0037 (8)	0.0031 (8)	−0.0006 (8)
C12	0.0327 (10)	0.0365 (11)	0.0397 (10)	0.0010 (8)	0.0042 (8)	−0.0037 (8)
C13	0.0421 (11)	0.0333 (11)	0.0386 (10)	0.0008 (8)	0.0059 (9)	−0.0051 (8)
C14	0.0612 (15)	0.0669 (16)	0.0717 (16)	−0.0230 (12)	0.0138 (12)	−0.0305 (13)
C15	0.0394 (11)	0.0354 (11)	0.0377 (10)	0.0025 (9)	0.0014 (8)	−0.0095 (8)
C16	0.0381 (10)	0.0334 (11)	0.0398 (10)	−0.0024 (9)	0.0032 (8)	−0.0055 (9)
C17	0.0346 (10)	0.0321 (10)	0.0375 (10)	−0.0002 (8)	0.0035 (8)	0.0006 (8)
C18	0.0380 (11)	0.0485 (12)	0.0439 (11)	0.0005 (9)	0.0023 (9)	−0.0094 (9)
C19	0.0543 (14)	0.0501 (13)	0.0470 (12)	−0.0003 (11)	0.0076 (10)	−0.0137 (10)
C20	0.0358 (12)	0.0746 (18)	0.0848 (18)	0.0100 (11)	−0.0004 (12)	−0.0158 (14)
C21	0.0396 (11)	0.0571 (14)	0.0568 (13)	−0.0008 (10)	−0.0009 (10)	−0.0131 (11)

Geometric parameters (Å, º)

O1—C8	1.357 (2)	C7—H7B	0.9700
O1—C7	1.439 (2)	C8—C9	1.378 (3)
O2—C13	1.369 (2)	C8—C13	1.410 (2)
O2—C14	1.415 (2)	C9—C10	1.394 (2)
O3—C16	1.220 (2)	C9—H9	0.9300
N1—C15	1.279 (2)	C10—C11	1.378 (2)
N1—N2	1.3821 (19)	C10—H10	0.9300
N2—C16	1.350 (2)	C11—C12	1.402 (2)
N2—H2	0.8600	C11—C15	1.455 (2)
N3—C19	1.321 (2)	C12—C13	1.376 (2)
N3—C20	1.329 (3)	C12—H12	0.9300
C1—C2	1.376 (3)	C14—H14A	0.9600
C1—C6	1.380 (3)	C14—H14B	0.9600
C1—H1	0.9300	C14—H14C	0.9600
C2—C3	1.364 (4)	C15—H15	0.9300
C2—H2A	0.9300	C16—C17	1.493 (2)
C3—C4	1.365 (4)	C17—C21	1.375 (2)
C3—H3	0.9300	C17—C18	1.380 (2)
C4—C5	1.387 (3)	C18—C19	1.378 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.377 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.381 (3)
C6—C7	1.498 (3)	C20—H20	0.9300
C7—H7A	0.9700	C21—H21	0.9300
C8—O1—C7	117.75 (14)	C11—C10—H10	119.7
C13—O2—C14	117.54 (14)	C9—C10—H10	119.7
C15—N1—N2	115.32 (15)	C10—C11—C12	119.18 (16)
C16—N2—N1	119.59 (15)	C10—C11—C15	119.53 (17)
C16—N2—H2	120.2	C12—C11—C15	121.26 (16)
N1—N2—H2	120.2	C13—C12—C11	120.65 (16)
C19—N3—C20	115.63 (17)	C13—C12—H12	119.7
C2—C1—C6	120.6 (2)	C11—C12—H12	119.7
C2—C1—H1	119.7	O2—C13—C12	125.25 (16)
C6—C1—H1	119.7	O2—C13—C8	115.07 (15)
C3—C2—C1	120.6 (3)	C12—C13—C8	119.66 (16)
C3—C2—H2A	119.7	O2—C14—H14A	109.5
C1—C2—H2A	119.7	O2—C14—H14B	109.5
C2—C3—C4	119.6 (3)	H14A—C14—H14B	109.5
C2—C3—H3	120.2	O2—C14—H14C	109.5
C4—C3—H3	120.2	H14A—C14—H14C	109.5
C3—C4—C5	120.2 (3)	H14B—C14—H14C	109.5
C3—C4—H4	119.9	N1—C15—C11	121.36 (17)
C5—C4—H4	119.9	N1—C15—H15	119.3
C6—C5—C4	120.5 (3)	C11—C15—H15	119.3
C6—C5—H5	119.7	O3—C16—N2	123.21 (16)
C4—C5—H5	119.7	O3—C16—C17	121.28 (16)
C5—C6—C1	118.5 (2)	N2—C16—C17	115.51 (16)
C5—C6—C7	121.2 (2)	C21—C17—C18	117.23 (17)
C1—C6—C7	120.3 (2)	C21—C17—C16	118.37 (17)
O1—C7—C6	107.08 (16)	C18—C17—C16	124.35 (16)
O1—C7—H7A	110.3	C19—C18—C17	119.26 (18)
C6—C7—H7A	110.3	C19—C18—H18	120.4
O1—C7—H7B	110.3	C17—C18—H18	120.4
C6—C7—H7B	110.3	N3—C19—C18	124.39 (19)
H7A—C7—H7B	108.6	N3—C19—H19	117.8
O1—C8—C9	125.00 (16)	C18—C19—H19	117.8
O1—C8—C13	115.32 (16)	N3—C20—C21	124.5 (2)
C9—C8—C13	119.68 (16)	N3—C20—H20	117.8
C8—C9—C10	120.11 (18)	C21—C20—H20	117.8
C8—C9—H9	119.9	C17—C21—C20	118.9 (2)
C10—C9—H9	119.9	C17—C21—H21	120.5
C11—C10—C9	120.68 (18)	C20—C21—H21	120.5
C15—N1—N2—C16	162.06 (17)	C11—C12—C13—O2	−178.59 (17)
C6—C1—C2—C3	0.6 (4)	C11—C12—C13—C8	−0.1 (3)
C1—C2—C3—C4	0.3 (5)	O1—C8—C13—O2	1.6 (2)
C2—C3—C4—C5	−0.7 (5)	C9—C8—C13—O2	−179.42 (17)
C3—C4—C5—C6	0.2 (4)	O1—C8—C13—C12	−177.06 (16)
C4—C5—C6—C1	0.6 (3)	C9—C8—C13—C12	1.9 (3)
C4—C5—C6—C7	−178.8 (2)	N2—N1—C15—C11	−176.09 (15)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C15—N1	−172.21 (18)
C2—C1—C6—C7	178.4 (2)	C12—C11—C15—N1	10.1 (3)
C8—O1—C7—C6	−169.98 (17)	N1—N2—C16—O3	4.5 (3)
C5—C6—C7—O1	−116.9 (2)	N1—N2—C16—C17	−175.35 (15)
C1—C6—C7—O1	63.7 (2)	O3—C16—C17—C21	−19.6 (3)
C7—O1—C8—C9	−7.4 (3)	N2—C16—C17—C21	160.22 (17)
C7—O1—C8—C13	171.56 (17)	O3—C16—C17—C18	157.82 (19)
O1—C8—C9—C10	176.25 (17)	N2—C16—C17—C18	−22.4 (3)
C13—C8—C9—C10	−2.6 (3)	C21—C17—C18—C19	2.3 (3)
C8—C9—C10—C11	1.5 (3)	C16—C17—C18—C19	−175.11 (18)
C9—C10—C11—C12	0.3 (3)	C20—N3—C19—C18	−1.5 (3)
C9—C10—C11—C15	−177.39 (17)	C17—C18—C19—N3	−1.0 (3)
C10—C11—C12—C13	−1.0 (3)	C19—N3—C20—C21	2.8 (4)
C15—C11—C12—C13	176.64 (17)	C18—C17—C21—C20	−1.2 (3)
C14—O2—C13—C12	−6.5 (3)	C16—C17—C21—C20	176.39 (19)
C14—O2—C13—C8	174.94 (18)	N3—C20—C21—C17	−1.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N3^i	0.93	2.55	3.475 (3)	174

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