Crystal structure of ethyl 4-[(E)-(4-hy­droxy-3-meth­oxy­benzyl­idene)amino]­benzoate: a p-hy­droxy Schiff base

Ling, J.; Kavuru, P.; Wojtas, L.; Chadwick, K.

doi:10.1107/S2056989016008999

Crystal structure of ethyl 4-[(E)-(4-hydroxy-3-methoxybenzylidene)amino]benzoate: a p-hydroxy Schiff base

J. Ling, P. Kavuru, L. Wojtas and K. Chadwick

The title p-hydroxy Schiff base, is the product of a condensation reaction between benzocaine and vanillin. The benzylidine and benzoate rings are inclined to one another by 24.58 (8)°, and the conformation about the C=N bond is E.

Keywords: crystal structure; p-hydroxy Schiff base; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016008999/su5304sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016008999/su5304Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989016008999/su5304sup3.pdf Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016008999/su5304Isup4.cml Supplementary material

CCDC reference: 1483394

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.121
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         85 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013) and SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013) and XPREP (Sheldrick,2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

Ethyl 4-[(E)-(4-hydroxy-3-methoxybenzylidene)amino]benzoate top

Crystal data top

C₁₇H₁₇NO₄	F(000) = 632
M_r = 299.31	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 12.4229 (5) Å	Cell parameters from 3549 reflections
b = 9.6392 (5) Å	θ = 11.5–68.2°
c = 13.2384 (6) Å	µ = 0.76 mm⁻¹
β = 102.457 (3)°	T = 296 K
V = 1547.94 (12) Å³	Block, colorless
Z = 4	0.26 × 0.11 × 0.04 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
ω scans	θ_max = 71.1°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −15→15
T_min = 0.599, T_max = 0.753	k = −11→11
18263 measured reflections	l = −15→16
2895 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0681P)² + 0.1332P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.23 e Å⁻³
2895 reflections	Δρ_min = −0.14 e Å⁻³
210 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0018 (4)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.40310 (9)	0.79734 (13)	0.24104 (8)	0.0566 (3)
C1	1.3086 (2)	−0.0296 (3)	0.5552 (2)	0.1030 (8)
H1A	1.2688	−0.0661	0.4904	0.155*
H1B	1.3627	−0.0959	0.5878	0.155*
H1C	1.3447	0.0551	0.5433	0.155*
C2	1.23138 (15)	−0.00168 (18)	0.62283 (15)	0.0675 (5)
H2A	1.1963	−0.0870	0.6375	0.081*
H2B	1.2702	0.0384	0.6877	0.081*
O3	1.14975 (10)	0.09453 (12)	0.56841 (10)	0.0647 (3)
C4	1.07204 (13)	0.13648 (19)	0.61646 (13)	0.0577 (4)
C5	0.99507 (12)	0.23783 (16)	0.55419 (12)	0.0512 (4)
C6	0.92059 (14)	0.3074 (2)	0.60045 (14)	0.0636 (5)
H6	0.9217	0.2925	0.6701	0.076*
C7	0.84532 (14)	0.3980 (2)	0.54458 (14)	0.0609 (4)
H7	0.7960	0.4438	0.5767	0.073*
C8	0.84222 (11)	0.42174 (15)	0.44046 (12)	0.0461 (3)
N1	0.75716 (9)	0.50849 (13)	0.38633 (9)	0.0464 (3)
C10	0.77038 (12)	0.57994 (15)	0.30896 (12)	0.0472 (3)
C11	0.68431 (12)	0.66679 (15)	0.24840 (11)	0.0442 (3)
C12	0.58421 (12)	0.68797 (15)	0.27877 (11)	0.0449 (3)
H12	0.5723	0.6466	0.3389	0.054*
C13	0.50380 (11)	0.76950 (14)	0.22013 (11)	0.0416 (3)
C14	0.52011 (11)	0.83080 (14)	0.12814 (10)	0.0419 (3)
O15	0.44049 (9)	0.90702 (12)	0.06788 (8)	0.0514 (3)
C16	0.38242 (16)	0.7484 (3)	0.33611 (15)	0.0777 (6)
H16A	0.3899	0.6493	0.3391	0.117*
H16B	0.3089	0.7735	0.3410	0.117*
H16C	0.4344	0.7893	0.3925	0.117*
O17	1.06660 (13)	0.09730 (18)	0.70144 (12)	0.0924 (5)
C18	0.99445 (13)	0.26473 (18)	0.45153 (13)	0.0565 (4)
H18	1.0455	0.2211	0.4202	0.068*
C19	0.91880 (13)	0.35567 (18)	0.39485 (12)	0.0545 (4)
H19	0.9193	0.3726	0.3258	0.065*
C20	0.70063 (12)	0.73037 (17)	0.15876 (12)	0.0504 (4)
H20	0.7673	0.7185	0.1387	0.060*
C21	0.61918 (12)	0.81096 (16)	0.09903 (11)	0.0492 (4)
H21	0.6312	0.8521	0.0389	0.059*
H15	0.3862 (18)	0.925 (2)	0.0989 (16)	0.077 (6)*
H10	0.8383 (16)	0.5785 (18)	0.2855 (14)	0.060 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0488 (6)	0.0743 (7)	0.0522 (6)	0.0172 (5)	0.0227 (5)	0.0181 (5)
C1	0.1014 (17)	0.1064 (18)	0.1052 (18)	0.0560 (15)	0.0308 (14)	0.0244 (15)
C2	0.0615 (10)	0.0546 (9)	0.0794 (12)	0.0128 (8)	−0.0002 (9)	0.0111 (8)
O3	0.0589 (7)	0.0652 (7)	0.0676 (7)	0.0188 (6)	0.0084 (6)	0.0122 (6)
C4	0.0489 (8)	0.0607 (10)	0.0612 (10)	0.0016 (7)	0.0069 (7)	0.0083 (7)
C5	0.0413 (7)	0.0544 (8)	0.0556 (9)	−0.0004 (6)	0.0057 (7)	0.0063 (7)
C6	0.0572 (9)	0.0845 (12)	0.0516 (9)	0.0134 (9)	0.0171 (8)	0.0164 (8)
C7	0.0524 (9)	0.0764 (11)	0.0585 (9)	0.0149 (8)	0.0217 (8)	0.0141 (8)
C8	0.0360 (7)	0.0497 (8)	0.0512 (8)	−0.0022 (6)	0.0067 (6)	0.0026 (6)
N1	0.0388 (6)	0.0501 (7)	0.0490 (7)	0.0018 (5)	0.0061 (5)	0.0021 (5)
C10	0.0381 (7)	0.0510 (8)	0.0520 (8)	−0.0007 (6)	0.0086 (6)	0.0004 (6)
C11	0.0416 (7)	0.0456 (7)	0.0451 (7)	−0.0002 (6)	0.0085 (6)	0.0000 (6)
C12	0.0472 (8)	0.0480 (8)	0.0405 (7)	0.0020 (6)	0.0114 (6)	0.0049 (6)
C13	0.0409 (7)	0.0450 (7)	0.0405 (7)	0.0005 (6)	0.0125 (6)	−0.0003 (6)
C14	0.0439 (7)	0.0435 (7)	0.0376 (7)	−0.0011 (6)	0.0071 (6)	0.0002 (5)
O15	0.0483 (6)	0.0630 (7)	0.0439 (6)	0.0092 (5)	0.0122 (5)	0.0125 (5)
C16	0.0667 (11)	0.1140 (17)	0.0626 (11)	0.0195 (11)	0.0365 (9)	0.0240 (11)
O17	0.0848 (10)	0.1206 (13)	0.0759 (9)	0.0343 (9)	0.0268 (8)	0.0444 (9)
C18	0.0503 (8)	0.0636 (10)	0.0564 (9)	0.0106 (7)	0.0131 (7)	0.0017 (7)
C19	0.0544 (9)	0.0625 (9)	0.0462 (8)	0.0100 (7)	0.0102 (7)	0.0034 (7)
C20	0.0415 (7)	0.0605 (9)	0.0523 (8)	0.0005 (7)	0.0170 (6)	0.0022 (7)
C21	0.0487 (8)	0.0596 (9)	0.0420 (7)	−0.0011 (7)	0.0152 (6)	0.0068 (6)

Geometric parameters (Å, º) top

O1—C13	1.3650 (17)	N1—C10	1.2739 (19)
O1—C16	1.418 (2)	C10—C11	1.455 (2)
C1—C2	1.471 (3)	C10—H10	0.960 (19)
C1—H1A	0.9600	C11—C20	1.389 (2)
C1—H1B	0.9600	C11—C12	1.402 (2)
C1—H1C	0.9600	C12—C13	1.372 (2)
C2—O3	1.446 (2)	C12—H12	0.9300
C2—H2A	0.9700	C13—C14	1.4070 (19)
C2—H2B	0.9700	C14—O15	1.3469 (17)
O3—C4	1.329 (2)	C14—C21	1.380 (2)
C4—O17	1.202 (2)	O15—H15	0.88 (2)
C4—C5	1.486 (2)	C16—H16A	0.9600
C5—C18	1.382 (2)	C16—H16B	0.9600
C5—C6	1.388 (2)	C16—H16C	0.9600
C6—C7	1.373 (2)	C18—C19	1.382 (2)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.390 (2)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.381 (2)
C8—C19	1.387 (2)	C20—H20	0.9300
C8—N1	1.4152 (18)	C21—H21	0.9300

C13—O1—C16	117.64 (12)	C11—C10—H10	115.0 (11)
C2—C1—H1A	109.5	C20—C11—C12	118.87 (13)
C2—C1—H1B	109.5	C20—C11—C10	119.95 (13)
H1A—C1—H1B	109.5	C12—C11—C10	121.18 (13)
C2—C1—H1C	109.5	C13—C12—C11	120.24 (13)
H1A—C1—H1C	109.5	C13—C12—H12	119.9
H1B—C1—H1C	109.5	C11—C12—H12	119.9
O3—C2—C1	107.05 (16)	O1—C13—C12	125.80 (13)
O3—C2—H2A	110.3	O1—C13—C14	113.73 (12)
C1—C2—H2A	110.3	C12—C13—C14	120.46 (13)
O3—C2—H2B	110.3	O15—C14—C21	119.69 (12)
C1—C2—H2B	110.3	O15—C14—C13	121.15 (12)
H2A—C2—H2B	108.6	C21—C14—C13	119.15 (13)
C4—O3—C2	117.42 (14)	C14—O15—H15	111.7 (14)
O17—C4—O3	123.07 (16)	O1—C16—H16A	109.5
O17—C4—C5	124.49 (16)	O1—C16—H16B	109.5
O3—C4—C5	112.43 (14)	H16A—C16—H16B	109.5
C18—C5—C6	118.72 (15)	O1—C16—H16C	109.5
C18—C5—C4	122.37 (15)	H16A—C16—H16C	109.5
C6—C5—C4	118.91 (15)	H16B—C16—H16C	109.5
C7—C6—C5	120.74 (15)	C19—C18—C5	120.78 (15)
C7—C6—H6	119.6	C19—C18—H18	119.6
C5—C6—H6	119.6	C5—C18—H18	119.6
C6—C7—C8	120.60 (15)	C18—C19—C8	120.32 (15)
C6—C7—H7	119.7	C18—C19—H19	119.8
C8—C7—H7	119.7	C8—C19—H19	119.8
C19—C8—C7	118.78 (14)	C21—C20—C11	120.90 (13)
C19—C8—N1	123.94 (14)	C21—C20—H20	119.6
C7—C8—N1	117.23 (13)	C11—C20—H20	119.6
C10—N1—C8	120.99 (12)	C14—C21—C20	120.36 (13)
N1—C10—C11	123.17 (13)	C14—C21—H21	119.8
N1—C10—H10	121.8 (11)	C20—C21—H21	119.8

C1—C2—O3—C4	−178.81 (19)	C16—O1—C13—C12	5.9 (2)
C2—O3—C4—O17	−0.7 (3)	C16—O1—C13—C14	−175.42 (16)
C2—O3—C4—C5	178.40 (14)	C11—C12—C13—O1	179.61 (14)
O17—C4—C5—C18	−170.41 (19)	C11—C12—C13—C14	1.1 (2)
O3—C4—C5—C18	10.6 (2)	O1—C13—C14—O15	−1.10 (19)
O17—C4—C5—C6	9.2 (3)	C12—C13—C14—O15	177.62 (13)
O3—C4—C5—C6	−169.87 (16)	O1—C13—C14—C21	179.55 (13)
C18—C5—C6—C7	2.0 (3)	C12—C13—C14—C21	−1.7 (2)
C4—C5—C6—C7	−177.54 (17)	C6—C5—C18—C19	−2.1 (3)
C5—C6—C7—C8	0.0 (3)	C4—C5—C18—C19	177.46 (16)
C6—C7—C8—C19	−2.0 (3)	C5—C18—C19—C8	0.1 (3)
C6—C7—C8—N1	175.45 (16)	C7—C8—C19—C18	1.9 (3)
C19—C8—N1—C10	−31.1 (2)	N1—C8—C19—C18	−175.34 (15)
C7—C8—N1—C10	151.56 (15)	C12—C11—C20—C21	−1.3 (2)
C8—N1—C10—C11	177.71 (13)	C10—C11—C20—C21	178.69 (14)
N1—C10—C11—C20	−173.29 (14)	O15—C14—C21—C20	−178.47 (14)
N1—C10—C11—C12	6.7 (2)	C13—C14—C21—C20	0.9 (2)
C20—C11—C12—C13	0.5 (2)	C11—C20—C21—C14	0.6 (2)
C10—C11—C12—C13	−179.54 (13)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C11–C14/C20/C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O15—H15···N1ⁱ	0.88 (2)	2.00 (2)	2.828 (2)	156 (2)
C2—H2B···Cg2ⁱⁱ	0.97	2.87	3.766 (2)	154

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

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Crystal structure of ethyl 4-[(E)-(4-hy­droxy-3-meth­oxy­benzyl­idene)amino]­benzoate: a p-hy­droxy Schiff base

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of ethyl 4-[(E)-(4-hydroxy-3-methoxybenzylidene)amino]benzoate: a p-hydroxy Schiff base