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

The molecule of the title compound, C₁₉H₂₂N₂O₃, is not planar. The vanillin residue makes dihedral angles of 4.84 (18) and 11.96 (7)° with the planes of the butyl group and the terminal benzene ring, respectively. Inter­molecular N—H...O and C—H...O hydrogen bonds help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.46 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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-Butoxy-3-methoxybenzylidene)benzohydrazide

Crystal data

C19H22N2O3	F(000) = 696
Mr = 326.39	Dx = 1.224 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1568 reflections
a = 7.583 (4) Å	θ = 2.3–21.7°
b = 24.124 (11) Å	µ = 0.08 mm^−1
c = 9.761 (5) Å	T = 294 K
β = 97.180 (8)°	Block, colorless
V = 1771.7 (14) Å^3	0.28 × 0.22 × 0.14 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3582 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 26.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.961, Tmax = 0.988	k = −16→30
9822 measured reflections	l = −11→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0493P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
3582 reflections	Δρmax = 0.14 e Å^−3
220 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (12)

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	0.4983 (2)	0.78303 (6)	0.29738 (15)	0.0603 (5)
O2	0.1021 (2)	0.53265 (5)	0.13797 (15)	0.0506 (5)
O3	0.1135 (2)	0.44918 (5)	0.30295 (15)	0.0531 (5)
N1	0.4536 (2)	0.74276 (6)	0.49846 (17)	0.0417 (5)
H1	0.4596	0.7454	0.5868	0.050*
N2	0.3945 (2)	0.69429 (7)	0.43232 (18)	0.0414 (5)
C1	0.5853 (3)	0.88432 (9)	0.4248 (2)	0.0518 (7)
H1A	0.5677	0.8826	0.3289	0.062*
C2	0.6373 (4)	0.93342 (10)	0.4889 (3)	0.0657 (8)
H2	0.6529	0.9648	0.4364	0.079*
C3	0.6659 (4)	0.93612 (10)	0.6294 (3)	0.0681 (8)
H3	0.7023	0.9692	0.6729	0.082*
C4	0.6409 (4)	0.89007 (10)	0.7060 (3)	0.0683 (8)
H4	0.6599	0.8921	0.8018	0.082*
C5	0.5879 (3)	0.84081 (9)	0.6431 (2)	0.0535 (7)
H5	0.5715	0.8097	0.6966	0.064*
C6	0.5588 (3)	0.83728 (8)	0.5010 (2)	0.0371 (6)
C7	0.5015 (3)	0.78578 (8)	0.4238 (2)	0.0387 (6)
C8	0.3707 (3)	0.65411 (9)	0.5126 (2)	0.0445 (6)
H8	0.3969	0.6589	0.6075	0.053*
C9	0.3030 (3)	0.60069 (8)	0.4588 (2)	0.0393 (6)
C10	0.3070 (3)	0.55583 (9)	0.5461 (2)	0.0534 (7)
H10	0.3514	0.5600	0.6387	0.064*
C11	0.2452 (3)	0.50440 (9)	0.4973 (2)	0.0541 (7)
H11	0.2496	0.4744	0.5574	0.065*
C12	0.1776 (3)	0.49759 (8)	0.3613 (2)	0.0422 (6)
C13	0.1712 (3)	0.54333 (8)	0.2711 (2)	0.0383 (6)
C14	0.2326 (3)	0.59383 (8)	0.3203 (2)	0.0413 (6)
H14	0.2275	0.6240	0.2607	0.050*
C15	0.1275 (3)	0.40095 (8)	0.3892 (2)	0.0515 (7)
H15A	0.0635	0.4068	0.4681	0.062*
H15B	0.2511	0.3938	0.4229	0.062*
C16	0.0497 (3)	0.35232 (8)	0.3055 (3)	0.0550 (7)
H16A	0.1119	0.3476	0.2253	0.066*
H16B	−0.0744	0.3597	0.2732	0.066*
C17	0.0641 (4)	0.29949 (9)	0.3901 (3)	0.0743 (9)
H17A	0.1880	0.2930	0.4243	0.089*
H17B	0.0001	0.3043	0.4693	0.089*
C18	−0.0087 (5)	0.24922 (10)	0.3095 (4)	0.1156 (13)
H18A	−0.1323	0.2549	0.2776	0.173*
H18B	0.0047	0.2171	0.3680	0.173*
H18C	0.0554	0.2438	0.2318	0.173*
C19	0.1068 (3)	0.57610 (9)	0.0388 (2)	0.0603 (8)
H19A	0.0366	0.6068	0.0635	0.090*
H19B	0.0597	0.5627	−0.0509	0.090*
H19C	0.2274	0.5880	0.0374	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1063 (15)	0.0443 (9)	0.0289 (9)	−0.0051 (9)	0.0033 (9)	−0.0003 (7)
O2	0.0756 (12)	0.0356 (8)	0.0368 (9)	−0.0095 (8)	−0.0076 (8)	−0.0010 (7)
O3	0.0814 (12)	0.0292 (8)	0.0468 (10)	−0.0105 (8)	0.0005 (9)	0.0009 (7)
N1	0.0656 (14)	0.0309 (10)	0.0277 (10)	−0.0060 (9)	0.0025 (9)	−0.0043 (9)
N2	0.0558 (13)	0.0334 (10)	0.0338 (11)	−0.0026 (9)	0.0004 (9)	−0.0045 (9)
C1	0.0733 (18)	0.0414 (13)	0.0405 (15)	−0.0059 (13)	0.0064 (13)	0.0045 (12)
C2	0.093 (2)	0.0413 (14)	0.065 (2)	−0.0171 (14)	0.0187 (16)	−0.0007 (14)
C3	0.091 (2)	0.0489 (15)	0.066 (2)	−0.0269 (15)	0.0182 (17)	−0.0158 (15)
C4	0.103 (2)	0.0554 (16)	0.0467 (16)	−0.0217 (17)	0.0118 (16)	−0.0138 (14)
C5	0.0811 (19)	0.0414 (13)	0.0376 (15)	−0.0134 (13)	0.0059 (13)	−0.0034 (12)
C6	0.0460 (15)	0.0319 (12)	0.0336 (13)	−0.0002 (11)	0.0059 (11)	−0.0009 (10)
C7	0.0503 (15)	0.0366 (13)	0.0284 (13)	0.0041 (11)	0.0015 (11)	0.0016 (11)
C8	0.0578 (17)	0.0407 (13)	0.0341 (13)	−0.0030 (12)	0.0019 (12)	−0.0037 (11)
C9	0.0498 (15)	0.0329 (12)	0.0340 (13)	−0.0030 (11)	0.0005 (11)	−0.0024 (10)
C10	0.0787 (19)	0.0440 (14)	0.0341 (13)	−0.0072 (13)	−0.0061 (13)	−0.0007 (12)
C11	0.083 (2)	0.0369 (13)	0.0399 (15)	−0.0088 (13)	−0.0035 (14)	0.0066 (11)
C12	0.0528 (16)	0.0304 (12)	0.0430 (15)	−0.0049 (11)	0.0041 (12)	−0.0018 (11)
C13	0.0444 (15)	0.0338 (12)	0.0360 (13)	−0.0015 (11)	0.0019 (11)	−0.0039 (11)
C14	0.0527 (16)	0.0322 (12)	0.0379 (14)	−0.0037 (11)	0.0005 (12)	0.0018 (11)
C15	0.0646 (18)	0.0333 (13)	0.0558 (16)	−0.0058 (12)	0.0043 (14)	0.0067 (12)
C16	0.0623 (18)	0.0357 (13)	0.0668 (18)	−0.0091 (12)	0.0076 (14)	−0.0021 (12)
C17	0.070 (2)	0.0357 (14)	0.114 (3)	−0.0019 (13)	−0.0015 (17)	0.0085 (15)
C18	0.111 (3)	0.0419 (16)	0.188 (4)	−0.0133 (17)	−0.006 (3)	−0.012 (2)
C19	0.090 (2)	0.0476 (15)	0.0394 (15)	−0.0159 (14)	−0.0087 (14)	0.0064 (12)

Geometric parameters (Å, º)

O1—C7	1.232 (2)	C9—C14	1.400 (3)
O2—C13	1.364 (2)	C10—C11	1.389 (3)
O2—C19	1.430 (2)	C10—H10	0.9300
O3—C12	1.362 (2)	C11—C12	1.372 (3)
O3—C15	1.432 (2)	C11—H11	0.9300
N1—C7	1.344 (2)	C12—C13	1.409 (3)
N1—N2	1.383 (2)	C13—C14	1.370 (3)
N1—H1	0.8600	C14—H14	0.9300
N2—C8	1.273 (3)	C15—C16	1.507 (3)
C1—C2	1.374 (3)	C15—H15A	0.9700
C1—C6	1.385 (3)	C15—H15B	0.9700
C1—H1A	0.9300	C16—C17	1.515 (3)
C2—C3	1.363 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.365 (3)	C17—C18	1.512 (4)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.374 (3)	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.380 (3)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—C7	1.490 (3)	C19—H19A	0.9600
C8—C9	1.460 (3)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—C10	1.375 (3)
C13—O2—C19	117.84 (16)	O3—C12—C11	125.3 (2)
C12—O3—C15	117.01 (17)	O3—C12—C13	115.29 (19)
C7—N1—N2	119.56 (17)	C11—C12—C13	119.4 (2)
C7—N1—H1	120.2	O2—C13—C14	125.13 (19)
N2—N1—H1	120.2	O2—C13—C12	115.27 (18)
C8—N2—N1	114.77 (18)	C14—C13—C12	119.6 (2)
C2—C1—C6	121.0 (2)	C13—C14—C9	121.0 (2)
C2—C1—H1A	119.5	C13—C14—H14	119.5
C6—C1—H1A	119.5	C9—C14—H14	119.5
C3—C2—C1	120.0 (2)	O3—C15—C16	108.58 (19)
C3—C2—H2	120.0	O3—C15—H15A	110.0
C1—C2—H2	120.0	C16—C15—H15A	110.0
C2—C3—C4	119.8 (2)	O3—C15—H15B	110.0
C2—C3—H3	120.1	C16—C15—H15B	110.0
C4—C3—H3	120.1	H15A—C15—H15B	108.4
C3—C4—C5	120.8 (2)	C15—C16—C17	111.3 (2)
C3—C4—H4	119.6	C15—C16—H16A	109.4
C5—C4—H4	119.6	C17—C16—H16A	109.4
C4—C5—C6	120.2 (2)	C15—C16—H16B	109.4
C4—C5—H5	119.9	C17—C16—H16B	109.4
C6—C5—H5	119.9	H16A—C16—H16B	108.0
C5—C6—C1	118.3 (2)	C18—C17—C16	113.2 (3)
C5—C6—C7	124.08 (19)	C18—C17—H17A	108.9
C1—C6—C7	117.6 (2)	C16—C17—H17A	108.9
O1—C7—N1	121.89 (19)	C18—C17—H17B	108.9
O1—C7—C6	121.3 (2)	C16—C17—H17B	108.9
N1—C7—C6	116.79 (18)	H17A—C17—H17B	107.7
N2—C8—C9	121.4 (2)	C17—C18—H18A	109.5
N2—C8—H8	119.3	C17—C18—H18B	109.5
C9—C8—H8	119.3	H18A—C18—H18B	109.5
C10—C9—C14	118.8 (2)	C17—C18—H18C	109.5
C10—C9—C8	119.5 (2)	H18A—C18—H18C	109.5
C14—C9—C8	121.72 (19)	H18B—C18—H18C	109.5
C9—C10—C11	120.7 (2)	O2—C19—H19A	109.5
C9—C10—H10	119.7	O2—C19—H19B	109.5
C11—C10—H10	119.7	H19A—C19—H19B	109.5
C12—C11—C10	120.5 (2)	O2—C19—H19C	109.5
C12—C11—H11	119.7	H19A—C19—H19C	109.5
C10—C11—H11	119.7	H19B—C19—H19C	109.5
C7—N1—N2—C8	172.8 (2)	C8—C9—C10—C11	−179.3 (2)
C6—C1—C2—C3	0.9 (4)	C9—C10—C11—C12	−0.6 (4)
C1—C2—C3—C4	−0.7 (4)	C15—O3—C12—C11	−3.7 (3)
C2—C3—C4—C5	0.3 (4)	C15—O3—C12—C13	176.3 (2)
C3—C4—C5—C6	−0.1 (4)	C10—C11—C12—O3	−179.9 (2)
C4—C5—C6—C1	0.3 (4)	C10—C11—C12—C13	0.0 (4)
C4—C5—C6—C7	179.9 (2)	C19—O2—C13—C14	5.4 (3)
C2—C1—C6—C5	−0.7 (4)	C19—O2—C13—C12	−174.5 (2)
C2—C1—C6—C7	179.6 (2)	O3—C12—C13—O2	−0.1 (3)
N2—N1—C7—O1	−1.6 (3)	C11—C12—C13—O2	180.0 (2)
N2—N1—C7—C6	178.27 (18)	O3—C12—C13—C14	180.0 (2)
C5—C6—C7—O1	−171.1 (2)	C11—C12—C13—C14	0.1 (3)
C1—C6—C7—O1	8.5 (3)	O2—C13—C14—C9	−179.4 (2)
C5—C6—C7—N1	9.0 (3)	C12—C13—C14—C9	0.5 (3)
C1—C6—C7—N1	−171.4 (2)	C10—C9—C14—C13	−1.1 (3)
N1—N2—C8—C9	177.96 (19)	C8—C9—C14—C13	179.4 (2)
N2—C8—C9—C10	169.2 (2)	C12—O3—C15—C16	−180.0 (2)
N2—C8—C9—C14	−11.3 (3)	O3—C15—C16—C17	178.7 (2)
C14—C9—C10—C11	1.1 (4)	C15—C16—C17—C18	−178.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.15	2.961 (3)	157
C5—H5···O1^i	0.93	2.53	3.451 (3)	169
C8—H8···O1^i	0.93	2.37	3.208 (3)	149

Symmetry code: (i) x, −y+3/2, z+1/2.