N-(2-{[(2E)-2-(2-Hydroxy­benzyl­idene)hydrazino]carbon­yl}phen­yl)benzamide

The title compound, C₂₁H₁₇N₃O₃ exhibits anti­fungal and anti­bacterial properties. The crystal structure is stabilized by a co-operative inter­play of both intra- and inter­molecular strong and weak hydrogen bonds of types O—H...N, N—H...O and C—H...O/N.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.098
• wR factor = 0.157
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

N-(2-{[(2E)-2-(2-hydroxybenzylidene)hydrazino]carbonyl}phenyl)benzamide

Crystal data

C21H17N3O3	F(000) = 1504
Mr = 359.38	Dx = 1.300 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 569 reflections
a = 21.226 (4) Å	θ = 1.4–25.4°
b = 8.362 (2) Å	µ = 0.09 mm^−1
c = 22.497 (4) Å	T = 290 K
β = 113.085 (4)°	Block, colourless
V = 3673.1 (12) Å^3	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer	3185 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→25
Tmin = 0.933, Tmax = 0.982	k = −9→9
12677 measured reflections	l = −26→26

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	All H-atom parameters refined
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.2154P] where P = (Fo^2 + 2Fc^2)/3
3185 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.15 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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.46286 (17)	0.2380 (4)	0.53451 (17)	0.0630 (9)
N2	0.45161 (16)	−0.2380 (4)	0.66298 (14)	0.0615 (9)
N3	0.49516 (17)	−0.1741 (4)	0.63766 (16)	0.0660 (10)
O1	0.44834 (13)	0.0704 (3)	0.63240 (12)	0.0752 (9)
O2	0.45434 (14)	0.3589 (3)	0.44103 (13)	0.0803 (9)
O3	0.36298 (17)	−0.2099 (4)	0.71587 (14)	0.0863 (10)
C1	0.3290 (3)	−0.4438 (9)	0.7513 (2)	0.0922 (16)
C2	0.3314 (3)	−0.6050 (10)	0.7593 (3)	0.113 (2)
C3	0.3718 (4)	−0.7005 (8)	0.7384 (3)	0.111 (2)
C4	0.4098 (3)	−0.6288 (6)	0.7083 (2)	0.0878 (15)
C5	0.4085 (2)	−0.4631 (5)	0.69941 (17)	0.0638 (11)
C6	0.3676 (2)	−0.3711 (6)	0.72183 (18)	0.0675 (11)
C7	0.4516 (2)	−0.3901 (6)	0.66987 (18)	0.0642 (12)
C8	0.4918 (2)	−0.0153 (5)	0.62514 (17)	0.0576 (10)
C9	0.5440 (2)	0.0451 (5)	0.60218 (18)	0.0575 (10)
C10	0.5284 (2)	0.1705 (5)	0.55658 (18)	0.0586 (11)
C11	0.5792 (3)	0.2229 (6)	0.5369 (3)	0.0770 (13)
C12	0.6436 (3)	0.1578 (6)	0.5624 (3)	0.0875 (16)
C13	0.6593 (3)	0.0368 (6)	0.6072 (3)	0.0834 (15)
C14	0.6097 (2)	−0.0169 (6)	0.6268 (2)	0.0732 (13)
C15	0.4304 (2)	0.3264 (4)	0.4813 (2)	0.0587 (11)
C16	0.3602 (2)	0.3809 (4)	0.4728 (2)	0.0575 (10)
C17	0.3149 (3)	0.4184 (6)	0.4117 (3)	0.0955 (16)
C18	0.2495 (4)	0.4706 (7)	0.4018 (4)	0.121 (2)
C19	0.2308 (3)	0.4928 (7)	0.4517 (5)	0.117 (2)
C20	0.2763 (3)	0.4568 (8)	0.5128 (4)	0.128 (2)
C21	0.3403 (2)	0.4009 (6)	0.5229 (3)	0.0863 (15)
H1N	0.4388 (17)	0.212 (4)	0.5592 (16)	0.068 (12)*
H3N	0.5169 (19)	−0.236 (5)	0.6197 (19)	0.100 (16)*
H1	0.301 (2)	−0.372 (6)	0.765 (2)	0.13 (2)*
H2	0.306 (2)	−0.657 (6)	0.778 (2)	0.12 (2)*
H3	0.373 (2)	−0.813 (5)	0.7433 (18)	0.102 (15)*
H4	0.4381 (19)	−0.687 (4)	0.6918 (18)	0.085 (14)*
H7	0.4826 (17)	−0.462 (4)	0.6572 (17)	0.082 (12)*
H11	0.5650 (18)	0.305 (4)	0.5047 (17)	0.070 (13)*
H12	0.6770 (18)	0.193 (4)	0.5496 (16)	0.080 (13)*
H13	0.7054 (18)	−0.001 (4)	0.6275 (16)	0.075 (11)*
H14	0.6177 (16)	−0.093 (4)	0.6591 (16)	0.075 (12)*
H17	0.335 (2)	0.409 (5)	0.379 (2)	0.111 (18)*
H18	0.226 (2)	0.501 (5)	0.360 (2)	0.113 (19)*
H19	0.187 (3)	0.528 (6)	0.447 (2)	0.14 (2)*
H20	0.263 (3)	0.448 (6)	0.547 (3)	0.15 (2)*
H21	0.3704 (18)	0.377 (4)	0.5653 (18)	0.078 (13)*
H3O	0.390 (3)	−0.183 (6)	0.697 (3)	0.16 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.082 (2)	0.0728 (19)	0.087 (2)	0.0275 (16)	0.0511 (18)	0.0078 (15)
O2	0.109 (2)	0.0752 (19)	0.076 (2)	0.0228 (16)	0.0574 (19)	0.0100 (15)
O3	0.102 (3)	0.086 (2)	0.083 (2)	0.0284 (19)	0.049 (2)	0.0116 (17)
N1	0.059 (2)	0.066 (2)	0.071 (3)	0.0136 (19)	0.034 (2)	0.0127 (19)
N2	0.073 (2)	0.063 (2)	0.053 (2)	0.0123 (18)	0.0293 (18)	0.0056 (17)
N3	0.075 (3)	0.066 (3)	0.068 (2)	0.015 (2)	0.041 (2)	0.0007 (19)
C1	0.099 (4)	0.108 (5)	0.070 (4)	−0.007 (4)	0.035 (3)	0.007 (3)
C2	0.120 (5)	0.135 (7)	0.091 (4)	−0.039 (5)	0.047 (4)	0.000 (4)
C3	0.170 (6)	0.075 (4)	0.081 (4)	−0.026 (4)	0.043 (4)	0.006 (3)
C4	0.127 (5)	0.071 (4)	0.066 (3)	0.004 (3)	0.038 (3)	−0.001 (3)
C5	0.082 (3)	0.066 (3)	0.041 (2)	0.004 (2)	0.022 (2)	−0.001 (2)
C6	0.075 (3)	0.077 (3)	0.045 (3)	0.007 (3)	0.017 (2)	0.007 (2)
C7	0.083 (3)	0.062 (3)	0.048 (3)	0.019 (2)	0.026 (2)	0.002 (2)
C8	0.066 (3)	0.058 (3)	0.050 (2)	0.013 (2)	0.025 (2)	−0.005 (2)
C9	0.053 (3)	0.063 (3)	0.056 (3)	0.008 (2)	0.021 (2)	−0.007 (2)
C10	0.056 (3)	0.060 (3)	0.064 (3)	0.003 (2)	0.028 (2)	−0.010 (2)
C11	0.070 (4)	0.063 (3)	0.106 (4)	0.004 (3)	0.043 (3)	0.001 (3)
C12	0.073 (4)	0.075 (3)	0.132 (5)	−0.007 (3)	0.059 (4)	−0.014 (3)
C13	0.045 (3)	0.089 (4)	0.110 (4)	0.010 (3)	0.023 (3)	−0.011 (3)
C14	0.066 (4)	0.081 (3)	0.071 (3)	0.006 (3)	0.025 (3)	−0.005 (3)
C15	0.076 (3)	0.045 (2)	0.060 (3)	0.008 (2)	0.032 (3)	−0.003 (2)
C16	0.063 (3)	0.049 (2)	0.057 (3)	0.007 (2)	0.019 (3)	0.001 (2)
C17	0.112 (5)	0.091 (4)	0.073 (4)	0.039 (3)	0.025 (4)	0.004 (3)
C18	0.118 (6)	0.105 (4)	0.091 (6)	0.045 (4)	−0.012 (5)	−0.006 (4)
C19	0.064 (5)	0.110 (5)	0.167 (8)	0.018 (4)	0.034 (5)	0.004 (5)
C20	0.078 (4)	0.187 (7)	0.132 (6)	0.049 (4)	0.056 (5)	0.048 (5)
C21	0.061 (3)	0.127 (4)	0.070 (4)	0.029 (3)	0.025 (3)	0.018 (3)

Geometric parameters (Å, º)

O3—C6	1.354 (5)	C6—C5	1.396 (5)
O3—H3O	0.88 (7)	C11—C12	1.371 (6)
N2—C7	1.281 (4)	C11—H11	0.96 (4)
N2—N3	1.371 (4)	C12—C13	1.374 (6)
O1—C8	1.229 (4)	C12—H12	0.91 (3)
O2—C15	1.232 (4)	C5—C4	1.398 (5)
C10—C11	1.387 (5)	C1—C2	1.358 (8)
C10—N1	1.400 (4)	C1—H1	0.97 (5)
C10—C9	1.412 (5)	C14—C13	1.365 (6)
C9—C14	1.384 (5)	C14—H14	0.93 (3)
C9—C8	1.483 (5)	C13—H13	0.96 (3)
C15—N1	1.344 (4)	C20—C19	1.367 (8)
C15—C16	1.496 (5)	C20—H20	0.93 (5)
C8—N3	1.353 (4)	C3—C4	1.378 (7)
N3—H3N	0.89 (5)	C3—C2	1.383 (8)
C16—C21	1.361 (5)	C3—H3	0.95 (4)
C16—C17	1.370 (5)	C4—H4	0.95 (5)
N1—H1N	0.92 (4)	C18—C19	1.342 (8)
C21—C20	1.370 (6)	C18—C17	1.387 (8)
C21—H21	0.94 (3)	C18—H18	0.91 (4)
C7—C5	1.458 (5)	C17—H17	0.98 (5)
C7—H7	1.01 (3)	C19—H19	0.95 (5)
C6—C1	1.380 (6)	C2—H2	0.92 (5)
C6—O3—H3O	106 (4)	C11—C12—H12	121 (2)
C7—N2—N3	118.1 (3)	C13—C12—H12	118 (2)
C11—C10—N1	123.2 (4)	C6—C5—C4	118.4 (4)
C11—C10—C9	118.5 (4)	C6—C5—C7	121.6 (4)
N1—C10—C9	118.3 (3)	C4—C5—C7	120.0 (4)
C14—C9—C10	118.7 (4)	C2—C1—C6	120.2 (6)
C14—C9—C8	120.4 (4)	C2—C1—H1	124 (3)
C10—C9—C8	120.8 (4)	C6—C1—H1	116 (3)
O2—C15—N1	124.1 (4)	C13—C14—C9	122.1 (5)
O2—C15—C16	121.1 (4)	C13—C14—H14	123 (2)
N1—C15—C16	114.8 (4)	C9—C14—H14	115 (2)
O1—C8—N3	121.7 (4)	C14—C13—C12	118.9 (5)
O1—C8—C9	123.4 (4)	C14—C13—H13	121 (2)
N3—C8—C9	114.9 (3)	C12—C13—H13	120 (2)
C8—N3—N2	118.7 (3)	C19—C20—C21	120.4 (7)
C8—N3—H3N	118 (3)	C19—C20—H20	122 (3)
N2—N3—H3N	121 (3)	C21—C20—H20	117 (3)
C21—C16—C17	118.7 (5)	C4—C3—C2	118.5 (6)
C21—C16—C15	123.2 (4)	C4—C3—H3	120 (3)
C17—C16—C15	118.0 (4)	C2—C3—H3	122 (3)
C15—N1—C10	129.0 (4)	C3—C4—C5	121.2 (5)
C15—N1—H1N	117 (2)	C3—C4—H4	123 (2)
C10—N1—H1N	114 (2)	C5—C4—H4	116 (2)
C16—C21—C20	120.9 (6)	C19—C18—C17	121.0 (6)
C16—C21—H21	120 (2)	C19—C18—H18	127 (3)
C20—C21—H21	119 (2)	C17—C18—H18	111 (3)
N2—C7—C5	120.1 (4)	C16—C17—C18	119.8 (6)
N2—C7—H7	122 (2)	C16—C17—H17	113 (3)
C5—C7—H7	118 (2)	C18—C17—H17	127 (3)
O3—C6—C1	116.9 (5)	C18—C19—C20	119.2 (6)
O3—C6—C5	123.0 (4)	C18—C19—H19	123 (3)
C1—C6—C5	120.1 (5)	C20—C19—H19	118 (3)
C12—C11—C10	120.9 (5)	C1—C2—C3	121.6 (6)
C12—C11—H11	125 (2)	C1—C2—H2	122 (3)
C10—C11—H11	115 (2)	C3—C2—H2	116 (3)
C11—C12—C13	120.9 (5)
C11—C10—C9—C14	2.0 (5)	C10—C11—C12—C13	1.3 (7)
N1—C10—C9—C14	−176.7 (3)	O3—C6—C5—C4	179.7 (4)
C11—C10—C9—C8	179.8 (3)	C1—C6—C5—C4	−0.7 (6)
N1—C10—C9—C8	1.1 (5)	O3—C6—C5—C7	2.3 (6)
C14—C9—C8—O1	143.4 (4)	C1—C6—C5—C7	−178.1 (4)
C10—C9—C8—O1	−34.4 (5)	N2—C7—C5—C6	−1.1 (6)
C14—C9—C8—N3	−36.7 (5)	N2—C7—C5—C4	−178.5 (4)
C10—C9—C8—N3	145.5 (3)	O3—C6—C1—C2	−179.5 (4)
O1—C8—N3—N2	−4.2 (6)	C5—C6—C1—C2	0.9 (7)
C9—C8—N3—N2	175.9 (3)	C10—C9—C14—C13	−1.5 (6)
C7—N2—N3—C8	174.6 (3)	C8—C9—C14—C13	−179.4 (4)
O2—C15—C16—C21	−155.6 (4)	C9—C14—C13—C12	1.0 (7)
N1—C15—C16—C21	26.1 (5)	C11—C12—C13—C14	−0.8 (7)
O2—C15—C16—C17	21.7 (5)	C16—C21—C20—C19	0.3 (9)
N1—C15—C16—C17	−156.6 (4)	C2—C3—C4—C5	0.6 (8)
O2—C15—N1—C10	2.3 (6)	C6—C5—C4—C3	0.0 (7)
C16—C15—N1—C10	−179.5 (3)	C7—C5—C4—C3	177.4 (4)
C11—C10—N1—C15	19.9 (6)	C21—C16—C17—C18	−2.1 (7)
C9—C10—N1—C15	−161.5 (4)	C15—C16—C17—C18	−179.5 (5)
C17—C16—C21—C20	0.3 (7)	C19—C18—C17—C16	3.4 (9)
C15—C16—C21—C20	177.5 (5)	C17—C18—C19—C20	−2.8 (10)
N3—N2—C7—C5	177.1 (3)	C21—C20—C19—C18	0.9 (10)
N1—C10—C11—C12	176.7 (4)	C6—C1—C2—C3	−0.3 (9)
C9—C10—C11—C12	−1.9 (6)	C4—C3—C2—C1	−0.5 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N2	0.88 (7)	1.81 (7)	2.601 (6)	150 (5)
N1—H1N···O1	0.92 (4)	1.97 (4)	2.728 (5)	139 (3)
N3—H3N···O2^i	0.89 (5)	1.99 (5)	2.857 (5)	165 (4)
C4—H4···O1^ii	0.95 (5)	2.49 (4)	3.317 (6)	146 (3)
C11—H11···O2	0.96 (4)	2.27 (3)	2.913 (5)	124 (3)
C14—H14···N3	0.93 (3)	2.55 (4)	2.858 (7)	100 (3)
C17—H17···O2	0.98 (5)	2.41 (4)	2.812 (7)	104 (3)

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