A new polymorph of N-(2-{N'-[(1E)-2-hy-droxy-benzyl-idene]hydrazinecarbon-yl}phen-yl)benzamide.

The title compound, C21H17N3O3, is a new polymorph of an already published structure [Shashidhar et al. (2006 ▶). Acta Cryst. E62, o4473-o4475]. The previously reported structure crystallizes in the monoclinic space group C2/c, whereas the structure reported here is in the tetra-gonal space group I41/a. The bond lengths and angles are similar in both structures. The mol-ecule adopts an extended conformation via intra-molecular N-H⋯O and O-H⋯N hydrogen bonds; the terminal phenyl ring and the hy-droxy-lphenyl ring are twisted with respect to the central benzene ring by 44.43 (7) and 21.99 (8)°, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions into a three-dimensional supra-molecular network.

Related literature

For different medicinal functions of hydrazide–hydrazone compounds, see: Bharti et al. (2010 ▶); Loncle et al. (2004 ▶); Garoufalias et al. (2002 ▶); Vicini et al. (2002 ▶); Sondhi et al. (2006 ▶); Kaymakçıoğlu & Rollas (2002 ▶); Rahman et al. (2005 ▶); Ragavendran et al. (2007 ▶); Çakır et al. (2001 ▶); Terzioglu & Gursoy (2003 ▶); Vicini et al. (2009 ▶). For a monoclinic polymorph of the title compound, see: Shashidhar et al. (2006 ▶).

Experimental

Crystal data

C21H17N3O3

M = 359.38

Tetragonal,

a = 26.7145 (14) Å

c = 10.1160 (5) Å

V = 7219.4 (8) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.22 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.80, T max = 0.99

37068 measured reflections

4868 independent reflections

3625 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.107

S = 1.04

4868 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010010/xu5789sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010010/xu5789Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010010/xu5789Isup3.cml

CCDC reference: 1000727

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H17N3O3	Dx = 1.323 Mg m−3
Mr = 359.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 9997 reflections
Hall symbol: -I 4ad	θ = 2.2–29.4°
a = 26.7145 (14) Å	µ = 0.09 mm−1
c = 10.1160 (5) Å	T = 150 K
V = 7219.4 (8) Å3	Block, pale-yellow
Z = 16	0.22 × 0.19 × 0.15 mm
F(000) = 3008

Bruker SMART APEX CCD diffractometer	4868 independent reflections
Radiation source: fine-focus sealed tube	3625 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.3660 pixels mm-1	θmax = 29.5°, θmin = 2.2°
φ and ω scans	h = −36→36
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −36→36
Tmin = 0.80, Tmax = 0.99	l = −13→13
37068 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0318P)2 + 5.367P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4868 reflections	Δρmax = 0.23 e Å−3
244 parameters	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O1	0.56564 (4)	0.41265 (4)	0.31994 (10)	0.0379 (3)
O2	0.65352 (4)	0.27173 (4)	0.11479 (12)	0.0444 (4)
O3	0.67750 (4)	0.17105 (4)	−0.15220 (12)	0.0461 (4)
N1	0.72994 (4)	0.23746 (4)	−0.02418 (12)	0.0323 (3)
N2	0.73567 (4)	0.27577 (4)	0.06534 (12)	0.0343 (4)
N3	0.61447 (4)	0.35295 (4)	0.22122 (12)	0.0327 (3)
C1	0.52568 (5)	0.35160 (5)	0.18534 (14)	0.0307 (4)
C2	0.52601 (5)	0.33600 (5)	0.05509 (16)	0.0372 (4)
C3	0.48315 (6)	0.31576 (6)	−0.00106 (17)	0.0416 (5)
C4	0.44051 (6)	0.30914 (5)	0.07402 (17)	0.0407 (5)
C5	0.44026 (6)	0.32438 (7)	0.20375 (18)	0.0521 (6)
C6	0.48221 (6)	0.34632 (7)	0.25975 (16)	0.0457 (5)
C7	0.57029 (5)	0.37577 (5)	0.24815 (14)	0.0302 (4)
C8	0.66281 (5)	0.36385 (5)	0.26991 (14)	0.0310 (4)
C9	0.67193 (6)	0.40316 (6)	0.35685 (16)	0.0401 (5)
C10	0.71960 (6)	0.41150 (6)	0.40559 (16)	0.0419 (5)
C11	0.75900 (6)	0.38104 (6)	0.36873 (15)	0.0389 (5)
C12	0.75057 (5)	0.34228 (5)	0.28113 (14)	0.0342 (4)
C13	0.70295 (5)	0.33311 (5)	0.22863 (14)	0.0298 (4)
C14	0.69475 (5)	0.29129 (5)	0.13280 (15)	0.0325 (4)
C15	0.76871 (5)	0.22376 (6)	−0.08880 (15)	0.0378 (5)
C16	0.76600 (5)	0.18314 (5)	−0.18336 (14)	0.0333 (4)
C17	0.80939 (6)	0.16779 (7)	−0.24892 (18)	0.0525 (6)
C18	0.80889 (7)	0.12900 (8)	−0.33838 (18)	0.0565 (6)
C19	0.76431 (6)	0.10478 (7)	−0.36461 (16)	0.0476 (5)
C20	0.72072 (6)	0.11928 (6)	−0.30239 (16)	0.0416 (5)
C21	0.72114 (5)	0.15829 (5)	−0.21138 (14)	0.0320 (4)
H2	0.55560	0.33910	0.00390	0.0450*
H2A	0.76580	0.29150	0.06880	0.0410*
H3	0.48320	0.30640	−0.09170	0.0500*
H3A	0.61360	0.32350	0.17590	0.0390*
H3B	0.68340	0.19490	−0.10030	0.0550*
H4	0.41160	0.29420	0.03630	0.0490*
H5	0.41100	0.31980	0.25570	0.0620*
H6	0.48130	0.35770	0.34870	0.0550*
H9	0.64520	0.42450	0.38300	0.0480*
H10	0.72530	0.43840	0.46500	0.0500*
H11	0.79160	0.38670	0.40330	0.0470*
H12	0.77770	0.32140	0.25590	0.0410*
H15	0.79970	0.24040	−0.07460	0.0450*
H17	0.84000	0.18460	−0.23130	0.0630*
H18	0.83880	0.11900	−0.38160	0.0680*
H19	0.76370	0.07790	−0.42610	0.0570*
H20	0.69020	0.10250	−0.32180	0.0500*

	U11	U22	U33	U12	U13	U23
O1	0.0422 (6)	0.0323 (5)	0.0391 (6)	0.0078 (4)	−0.0023 (4)	−0.0068 (4)
O2	0.0287 (5)	0.0375 (6)	0.0669 (8)	−0.0050 (4)	0.0089 (5)	−0.0155 (5)
O3	0.0265 (5)	0.0485 (6)	0.0633 (8)	−0.0034 (4)	0.0024 (5)	−0.0142 (5)
N1	0.0298 (6)	0.0300 (6)	0.0370 (6)	0.0003 (4)	0.0016 (5)	−0.0009 (5)
N2	0.0283 (6)	0.0334 (6)	0.0412 (7)	−0.0039 (5)	0.0043 (5)	−0.0057 (5)
N3	0.0301 (6)	0.0276 (5)	0.0404 (7)	0.0001 (4)	0.0010 (5)	−0.0059 (5)
C1	0.0298 (6)	0.0250 (6)	0.0372 (7)	0.0026 (5)	0.0028 (6)	0.0027 (5)
C2	0.0300 (7)	0.0372 (7)	0.0444 (9)	−0.0025 (6)	0.0084 (6)	−0.0096 (6)
C3	0.0362 (8)	0.0401 (8)	0.0485 (9)	−0.0030 (6)	0.0035 (7)	−0.0153 (7)
C4	0.0318 (7)	0.0340 (7)	0.0564 (10)	−0.0049 (6)	0.0011 (7)	0.0010 (7)
C5	0.0329 (8)	0.0766 (12)	0.0467 (10)	−0.0075 (8)	0.0087 (7)	0.0117 (9)
C6	0.0364 (8)	0.0676 (11)	0.0332 (8)	−0.0010 (7)	0.0047 (6)	0.0041 (7)
C7	0.0334 (7)	0.0261 (6)	0.0310 (7)	0.0022 (5)	0.0029 (5)	0.0023 (5)
C8	0.0320 (7)	0.0292 (6)	0.0318 (7)	−0.0013 (5)	0.0013 (5)	0.0026 (5)
C9	0.0398 (8)	0.0375 (8)	0.0430 (9)	0.0015 (6)	−0.0007 (7)	−0.0071 (7)
C10	0.0448 (8)	0.0431 (8)	0.0379 (8)	−0.0041 (7)	−0.0041 (7)	−0.0067 (7)
C11	0.0355 (7)	0.0481 (9)	0.0330 (8)	−0.0050 (6)	−0.0040 (6)	0.0011 (6)
C12	0.0322 (7)	0.0374 (7)	0.0331 (7)	−0.0010 (5)	0.0033 (6)	0.0039 (6)
C13	0.0317 (7)	0.0278 (6)	0.0298 (7)	−0.0026 (5)	0.0042 (5)	0.0035 (5)
C14	0.0303 (7)	0.0275 (6)	0.0398 (8)	−0.0007 (5)	0.0047 (6)	0.0022 (6)
C15	0.0265 (7)	0.0440 (8)	0.0428 (9)	−0.0055 (6)	0.0024 (6)	−0.0054 (7)
C16	0.0270 (6)	0.0403 (8)	0.0325 (7)	−0.0001 (5)	−0.0004 (5)	−0.0015 (6)
C17	0.0299 (8)	0.0763 (12)	0.0514 (10)	−0.0046 (8)	0.0050 (7)	−0.0231 (9)
C18	0.0407 (9)	0.0768 (13)	0.0520 (11)	0.0056 (8)	0.0063 (8)	−0.0239 (9)
C19	0.0531 (10)	0.0507 (9)	0.0390 (9)	0.0032 (7)	−0.0011 (7)	−0.0118 (7)
C20	0.0407 (8)	0.0441 (8)	0.0399 (9)	−0.0047 (7)	−0.0063 (7)	−0.0033 (7)
C21	0.0284 (6)	0.0339 (7)	0.0336 (7)	0.0020 (5)	−0.0023 (5)	0.0049 (6)

O1—C7	1.2303 (17)	C12—C13	1.4002 (19)
O2—C14	1.2326 (17)	C13—C14	1.495 (2)
O3—C21	1.3542 (17)	C15—C16	1.448 (2)
O3—H3B	0.8400	C16—C21	1.3990 (19)
N1—N2	1.3751 (16)	C16—C17	1.397 (2)
N1—C15	1.2783 (18)	C17—C18	1.376 (3)
N2—C14	1.3537 (18)	C18—C19	1.381 (3)
N3—C7	1.3560 (17)	C19—C20	1.379 (2)
N3—C8	1.4125 (17)	C20—C21	1.391 (2)
N2—H2A	0.9100	C2—H2	0.9500
N3—H3A	0.9100	C3—H3	0.9500
C1—C7	1.4970 (19)	C4—H4	0.9500
C1—C2	1.382 (2)	C5—H5	0.9500
C1—C6	1.391 (2)	C6—H6	0.9500
C2—C3	1.388 (2)	C9—H9	0.9500
C3—C4	1.381 (2)	C10—H10	0.9500
C4—C5	1.374 (2)	C11—H11	0.9500
C5—C6	1.386 (2)	C12—H12	0.9500
C8—C13	1.4137 (19)	C15—H15	0.9500
C8—C9	1.391 (2)	C17—H17	0.9500
C9—C10	1.384 (2)	C18—H18	0.9500
C10—C11	1.382 (2)	C19—H19	0.9500
C11—C12	1.381 (2)	C20—H20	0.9500
C21—O3—H3B	108.00	C16—C17—C18	121.69 (15)
N2—N1—C15	117.37 (11)	C17—C18—C19	119.18 (17)
N1—N2—C14	118.04 (11)	C18—C19—C20	120.59 (17)
C7—N3—C8	129.27 (12)	C19—C20—C21	120.38 (15)
C14—N2—H2A	124.00	O3—C21—C20	118.32 (13)
N1—N2—H2A	118.00	C16—C21—C20	119.78 (13)
C7—N3—H3A	118.00	O3—C21—C16	121.90 (12)
C8—N3—H3A	112.00	C1—C2—H2	120.00
C6—C1—C7	118.60 (13)	C3—C2—H2	120.00
C2—C1—C6	119.38 (13)	C2—C3—H3	120.00
C2—C1—C7	121.98 (12)	C4—C3—H3	120.00
C1—C2—C3	120.16 (14)	C3—C4—H4	120.00
C2—C3—C4	120.37 (15)	C5—C4—H4	120.00
C3—C4—C5	119.44 (15)	C4—C5—H5	120.00
C4—C5—C6	120.79 (15)	C6—C5—H5	120.00
C1—C6—C5	119.79 (15)	C1—C6—H6	120.00
N3—C7—C1	114.44 (12)	C5—C6—H6	120.00
O1—C7—N3	124.51 (13)	C8—C9—H9	120.00
O1—C7—C1	121.04 (12)	C10—C9—H9	120.00
N3—C8—C13	118.08 (12)	C9—C10—H10	120.00
N3—C8—C9	122.42 (12)	C11—C10—H10	120.00
C9—C8—C13	119.50 (13)	C10—C11—H11	120.00
C8—C9—C10	120.53 (14)	C12—C11—H11	120.00
C9—C10—C11	120.67 (15)	C11—C12—H12	119.00
C10—C11—C12	119.37 (14)	C13—C12—H12	119.00
C11—C12—C13	121.51 (13)	N1—C15—H15	120.00
C8—C13—C14	120.96 (12)	C16—C15—H15	120.00
C8—C13—C12	118.39 (12)	C16—C17—H17	119.00
C12—C13—C14	120.65 (12)	C18—C17—H17	119.00
O2—C14—N2	121.15 (13)	C17—C18—H18	120.00
O2—C14—C13	122.92 (13)	C19—C18—H18	120.00
N2—C14—C13	115.94 (11)	C18—C19—H19	120.00
N1—C15—C16	120.78 (13)	C20—C19—H19	120.00
C15—C16—C21	122.15 (12)	C19—C20—H20	120.00
C17—C16—C21	118.38 (13)	C21—C20—H20	120.00
C15—C16—C17	119.47 (13)
C15—N1—N2—C14	178.84 (13)	C9—C8—C13—C12	2.4 (2)
N2—N1—C15—C16	178.99 (12)	C9—C8—C13—C14	−178.53 (13)
N1—N2—C14—O2	0.0 (2)	C8—C9—C10—C11	0.1 (2)
N1—N2—C14—C13	−179.85 (11)	C9—C10—C11—C12	0.7 (2)
C8—N3—C7—O1	2.7 (2)	C10—C11—C12—C13	0.0 (2)
C8—N3—C7—C1	−175.82 (13)	C11—C12—C13—C8	−1.6 (2)
C7—N3—C8—C9	−1.3 (2)	C11—C12—C13—C14	179.33 (13)
C7—N3—C8—C13	178.23 (13)	C8—C13—C14—O2	−22.0 (2)
C6—C1—C2—C3	0.7 (2)	C8—C13—C14—N2	157.86 (13)
C7—C1—C2—C3	−177.16 (13)	C12—C13—C14—O2	157.06 (14)
C2—C1—C6—C5	1.7 (2)	C12—C13—C14—N2	−23.07 (19)
C7—C1—C6—C5	179.57 (15)	N1—C15—C16—C17	−177.66 (15)
C2—C1—C7—O1	137.04 (15)	N1—C15—C16—C21	2.1 (2)
C2—C1—C7—N3	−44.39 (18)	C15—C16—C17—C18	179.19 (16)
C6—C1—C7—O1	−40.8 (2)	C21—C16—C17—C18	−0.5 (2)
C6—C1—C7—N3	137.75 (14)	C15—C16—C21—O3	0.5 (2)
C1—C2—C3—C4	−2.7 (2)	C15—C16—C21—C20	−179.54 (14)
C2—C3—C4—C5	2.3 (2)	C17—C16—C21—O3	−179.83 (14)
C3—C4—C5—C6	0.1 (3)	C17—C16—C21—C20	0.2 (2)
C4—C5—C6—C1	−2.1 (3)	C16—C17—C18—C19	0.4 (3)
N3—C8—C9—C10	177.83 (14)	C17—C18—C19—C20	0.2 (3)
C13—C8—C9—C10	−1.7 (2)	C18—C19—C20—C21	−0.5 (3)
N3—C8—C13—C12	−177.16 (12)	C19—C20—C21—O3	−179.64 (14)
N3—C8—C13—C14	1.9 (2)	C19—C20—C21—C16	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.91	2.02	2.9181 (15)	171
N3—H3A···O2	0.91	1.85	2.6373 (16)	143
O3—H3B···N1	0.84	1.85	2.6052 (16)	148
C4—H4···O2ii	0.95	2.60	3.3388 (19)	135
C9—H9···O1	0.95	2.24	2.8751 (19)	123
C12—H12···O1i	0.95	2.47	3.2319 (17)	137
C18—H18···O3iii	0.95	2.53	3.417 (2)	155
C17—H17···Cg1i	0.95	2.73	3.6561 (18)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.91	2.02	2.9181 (15)	171
N3—H3A⋯O2	0.91	1.85	2.6373 (16)	143
O3—H3B⋯N1	0.84	1.85	2.6052 (16)	148
C4—H4⋯O2ii	0.95	2.60	3.3388 (19)	135
C12—H12⋯O1i	0.95	2.47	3.2319 (17)	137
C18—H18⋯O3iii	0.95	2.53	3.417 (2)	155
C17—H17⋯Cg1i	0.95	2.73	3.6561 (18)	166

Symmetry codes: (i) ; (ii) ; (iii) .