(E)-2-Hydr­oxy-N′-[1-(4-methoxy­phen­yl)ethyl­idene]benzohydrazide

Qiu, X.-Y.; Luo, Q.-Y.; Yang, S.-L.; Liu, W.-S.

doi:10.1107/S1600536806029345

(E)-2-Hydroxy-N′-[1-(4-methoxyphenyl)ethylidene]benzohydrazide

X.-Y. Qiu, Q.-Y. Luo, S.-L. Yang and W.-S. Liu

The title molecule, C₁₆H₁₆N₂O₃, adopts a trans configuration with respect to the C=N double bond. The dihedral angle between the two rings is 47.2 (3)°. The crystal structure is stabilized by intermolecular O—H

O hydrogen bonds, which link the molecules into a chain parallel to the b axis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029345/wk2022sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029345/wk2022Isup2.hkl Contains datablock I

CCDC reference: 625012

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.102
Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.19
           From the CIF: _reflns_number_total               1992
           Count of symmetry unique reflns         2014
           Completeness (_total/calc)             98.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 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
   0 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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-hydroxy-N'-[1-(4-methoxyphenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 600
M_r = 284.31	D_x = 1.328 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1678 reflections
a = 7.4007 (15) Å	θ = 4.2–26°
b = 11.794 (2) Å	µ = 0.09 mm⁻¹
c = 16.290 (3) Å	T = 298 K
V = 1421.8 (5) Å³	Block, colourless
Z = 4	0.26 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	1992 independent reflections
Radiation source: fine-focus sealed tube	1341 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 28.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.984, T_max = 0.991	k = −15→15
10760 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0368P)² + 0.1085P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1992 reflections	Δρ_max = 0.12 e Å⁻³
193 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Special details top

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 > σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	1.0333 (3)	0.84602 (14)	0.35529 (10)	0.0624 (5)
H1	0.9991	0.7776	0.3455	0.075*
O1	0.9267 (3)	0.69682 (13)	0.24793 (9)	0.0787 (5)
H1A	0.8824	0.6399	0.2272	0.118*
C1	1.0049 (3)	0.76118 (18)	0.18847 (12)	0.0594 (5)
O2	1.1725 (3)	1.00287 (13)	0.30866 (9)	0.0704 (5)
N2	1.0173 (3)	0.89007 (15)	0.43330 (10)	0.0632 (5)
C2	0.9985 (4)	0.7269 (2)	0.10669 (13)	0.0692 (6)
H2	0.9400	0.6599	0.0925	0.083*
C3	1.0786 (4)	0.7921 (2)	0.04704 (14)	0.0766 (7)
H3	1.0742	0.7686	−0.0074	0.092*
O4	0.8539 (3)	1.01502 (19)	0.80026 (10)	0.0977 (7)
C4	1.1651 (4)	0.8917 (2)	0.06683 (13)	0.0763 (7)
H4	1.2190	0.9355	0.0261	0.092*
C5	1.1711 (3)	0.9258 (2)	0.14772 (14)	0.0670 (6)
H5	1.2301	0.9929	0.1611	0.080*
C6	1.0911 (3)	0.86257 (17)	0.20981 (12)	0.0551 (5)
C7	1.1016 (3)	0.90927 (18)	0.29476 (12)	0.0578 (5)
C8	0.9673 (3)	0.81891 (19)	0.48914 (13)	0.0577 (5)
C9	0.9376 (3)	0.86631 (18)	0.57170 (13)	0.0590 (5)
C10	0.9631 (3)	0.8029 (2)	0.64255 (13)	0.0680 (6)
H10	0.9977	0.7273	0.6381	0.082*
C11	0.9382 (4)	0.8497 (2)	0.71964 (14)	0.0737 (7)
H11	0.9585	0.8061	0.7663	0.088*
C12	0.8831 (4)	0.9611 (2)	0.72732 (14)	0.0715 (7)
C13	0.8561 (4)	1.0251 (2)	0.65774 (15)	0.0750 (7)
H13	0.8190	1.1002	0.6625	0.090*
C14	0.8836 (3)	0.9789 (2)	0.58119 (13)	0.0661 (6)
H14	0.8659	1.0236	0.5349	0.079*
C15	0.8983 (5)	0.9563 (3)	0.87323 (15)	0.1013 (10)
H15A	0.8289	0.8877	0.8764	0.152*
H15B	0.8713	1.0033	0.9198	0.152*
H15C	1.0247	0.9382	0.8731	0.152*
C16	0.9374 (4)	0.69470 (19)	0.47364 (15)	0.0727 (7)
H16A	0.8401	0.6852	0.4352	0.109*
H16B	0.9072	0.6577	0.5243	0.109*
H16C	1.0456	0.6619	0.4515	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0800 (13)	0.0548 (9)	0.0524 (9)	−0.0006 (9)	0.0019 (9)	−0.0030 (8)
O1	0.1087 (15)	0.0667 (9)	0.0608 (9)	−0.0212 (10)	0.0095 (9)	−0.0056 (8)
C1	0.0644 (14)	0.0578 (11)	0.0562 (11)	0.0041 (12)	−0.0001 (10)	0.0018 (10)
O2	0.0884 (13)	0.0572 (9)	0.0657 (9)	−0.0069 (9)	−0.0091 (8)	0.0009 (7)
N2	0.0744 (13)	0.0620 (10)	0.0532 (9)	0.0035 (10)	−0.0030 (9)	−0.0043 (8)
C2	0.0839 (18)	0.0635 (13)	0.0602 (12)	0.0029 (13)	−0.0043 (12)	−0.0055 (11)
C3	0.099 (2)	0.0743 (15)	0.0563 (12)	0.0055 (16)	−0.0009 (13)	−0.0039 (11)
O4	0.1067 (16)	0.1218 (16)	0.0645 (10)	0.0087 (13)	0.0135 (10)	−0.0210 (11)
C4	0.0973 (19)	0.0744 (15)	0.0573 (13)	0.0022 (15)	0.0070 (13)	0.0086 (12)
C5	0.0720 (15)	0.0629 (13)	0.0661 (13)	0.0004 (12)	0.0013 (12)	0.0037 (11)
C6	0.0580 (13)	0.0525 (11)	0.0546 (11)	0.0066 (11)	−0.0012 (9)	0.0010 (9)
C7	0.0594 (13)	0.0546 (11)	0.0593 (12)	0.0091 (11)	−0.0045 (10)	0.0014 (10)
C8	0.0537 (13)	0.0617 (12)	0.0576 (11)	0.0032 (11)	−0.0024 (10)	−0.0029 (10)
C9	0.0550 (13)	0.0641 (13)	0.0579 (11)	−0.0012 (11)	−0.0020 (10)	−0.0002 (10)
C10	0.0750 (15)	0.0662 (12)	0.0629 (12)	−0.0017 (12)	0.0045 (12)	0.0016 (11)
C11	0.0784 (17)	0.0849 (16)	0.0577 (13)	−0.0044 (14)	0.0061 (11)	0.0063 (12)
C12	0.0649 (16)	0.0895 (17)	0.0602 (13)	0.0008 (14)	0.0086 (11)	−0.0126 (12)
C13	0.0742 (17)	0.0760 (15)	0.0747 (16)	0.0145 (13)	0.0002 (13)	−0.0112 (13)
C14	0.0657 (15)	0.0716 (14)	0.0608 (12)	0.0078 (13)	−0.0056 (11)	−0.0009 (11)
C15	0.111 (2)	0.138 (3)	0.0544 (14)	−0.024 (2)	0.0220 (15)	−0.0117 (15)
C16	0.0789 (18)	0.0654 (14)	0.0739 (14)	−0.0056 (13)	0.0075 (12)	−0.0049 (12)

Geometric parameters (Å, º) top

N1—C7	1.336 (3)	C6—C7	1.491 (3)
N1—N2	1.378 (2)	C8—C9	1.473 (3)
N1—H1	0.8600	C8—C16	1.503 (3)
O1—C1	1.360 (3)	C9—C10	1.388 (3)
O1—H1A	0.8200	C9—C14	1.395 (3)
C1—C2	1.393 (3)	C10—C11	1.384 (3)
C1—C6	1.399 (3)	C10—H10	0.9300
O2—C7	1.243 (3)	C11—C12	1.381 (4)
N2—C8	1.292 (3)	C11—H11	0.9300
C2—C3	1.374 (3)	C12—C13	1.377 (3)
C2—H2	0.9300	C13—C14	1.376 (3)
C3—C4	1.377 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
O4—C12	1.365 (3)	C15—H15A	0.9600
O4—C15	1.414 (3)	C15—H15B	0.9600
C4—C5	1.378 (3)	C15—H15C	0.9600
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.389 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600

C7—N1—N2	120.18 (17)	C10—C9—C14	117.4 (2)
C7—N1—H1	119.9	C10—C9—C8	122.3 (2)
N2—N1—H1	119.9	C14—C9—C8	120.3 (2)
C1—O1—H1A	109.5	C11—C10—C9	121.4 (2)
O1—C1—C2	120.3 (2)	C11—C10—H10	119.3
O1—C1—C6	119.61 (17)	C9—C10—H10	119.3
C2—C1—C6	120.1 (2)	C12—C11—C10	120.1 (2)
C8—N2—N1	115.41 (17)	C12—C11—H11	120.0
C3—C2—C1	119.9 (2)	C10—C11—H11	120.0
C3—C2—H2	120.0	O4—C12—C13	116.0 (2)
C1—C2—H2	120.0	O4—C12—C11	124.7 (2)
C2—C3—C4	120.9 (2)	C13—C12—C11	119.3 (2)
C2—C3—H3	119.6	C14—C13—C12	120.5 (2)
C4—C3—H3	119.6	C14—C13—H13	119.8
C12—O4—C15	117.8 (2)	C12—C13—H13	119.8
C3—C4—C5	119.2 (2)	C13—C14—C9	121.3 (2)
C3—C4—H4	120.4	C13—C14—H14	119.3
C5—C4—H4	120.4	C9—C14—H14	119.3
C4—C5—C6	121.7 (2)	O4—C15—H15A	109.5
C4—C5—H5	119.1	O4—C15—H15B	109.5
C6—C5—H5	119.1	H15A—C15—H15B	109.5
C5—C6—C1	118.17 (19)	O4—C15—H15C	109.5
C5—C6—C7	117.08 (19)	H15A—C15—H15C	109.5
C1—C6—C7	124.74 (19)	H15B—C15—H15C	109.5
O2—C7—N1	121.42 (19)	C8—C16—H16A	109.5
O2—C7—C6	121.26 (19)	C8—C16—H16B	109.5
N1—C7—C6	117.31 (19)	H16A—C16—H16B	109.5
N2—C8—C9	116.05 (19)	C8—C16—H16C	109.5
N2—C8—C16	123.9 (2)	H16A—C16—H16C	109.5
C9—C8—C16	120.1 (2)	H16B—C16—H16C	109.5

C7—N1—N2—C8	−173.2 (2)	N1—N2—C8—C9	−175.98 (19)
O1—C1—C2—C3	−179.7 (2)	N1—N2—C8—C16	3.3 (3)
C6—C1—C2—C3	0.7 (4)	N2—C8—C9—C10	−150.6 (2)
C1—C2—C3—C4	−0.2 (4)	C16—C8—C9—C10	30.0 (3)
C2—C3—C4—C5	0.1 (4)	N2—C8—C9—C14	28.7 (3)
C3—C4—C5—C6	−0.3 (4)	C16—C8—C9—C14	−150.6 (2)
C4—C5—C6—C1	0.8 (3)	C14—C9—C10—C11	−0.7 (4)
C4—C5—C6—C7	−178.4 (2)	C8—C9—C10—C11	178.6 (2)
O1—C1—C6—C5	179.4 (2)	C9—C10—C11—C12	1.3 (4)
C2—C1—C6—C5	−1.0 (3)	C15—O4—C12—C13	−173.5 (2)
O1—C1—C6—C7	−1.5 (3)	C15—O4—C12—C11	5.9 (4)
C2—C1—C6—C7	178.1 (2)	C10—C11—C12—O4	179.7 (3)
N2—N1—C7—O2	9.0 (3)	C10—C11—C12—C13	−0.9 (4)
N2—N1—C7—C6	−171.57 (18)	O4—C12—C13—C14	179.4 (2)
C5—C6—C7—O2	2.8 (3)	C11—C12—C13—C14	0.0 (4)
C1—C6—C7—O2	−176.3 (2)	C12—C13—C14—C9	0.7 (4)
C5—C6—C7—N1	−176.6 (2)	C10—C9—C14—C13	−0.3 (4)
C1—C6—C7—N1	4.3 (3)	C8—C9—C14—C13	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.93	2.603 (2)	134
O1—H1A···O2ⁱ	0.82	1.77	2.573 (2)	168

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

(E)-2-Hydr­oxy-N′-[1-(4-methoxy­phen­yl)ethyl­idene]benzohydrazide

Supporting information

Key indicators

checkCIF/PLATON results

(E)-2-Hydroxy-N′-[1-(4-methoxyphenyl)ethylidene]benzohydrazide