Benzyl N-(1-{N'-[(E)-2-chloro-benzyl-idene]hydrazinecarbon-yl}-2-hy-droxy-eth-yl)carbamate.

The mol-ecule of the title compound, C(18)H(18)ClN(3)O(4), is twisted about the chiral C atom with the dihedral angle between the two amide residues being 87.8 (5)°, but, overall, it can be described as curved, with the benzene rings lying on the same side of the mol-ecule [dihedral angle = 62.8 (4)°]. The conformation about the imine bond [1.294 (7) Å] is E. In the crystal, a two-dimensional array in the ab plane is mediated by O-H⋯O and N-H⋯O hydrogen bonds as well as C-H⋯Cl inter-actions. The layers stack along the c-axis direction, being connected by C-H⋯.π contacts.

Related literature

For background to the use of l-serine derivatives in anti-tumour therapy, see: Jiao et al. (2009 ▶); Yakura et al. (2007 ▶). For background to N-acyl­hydrazone derivatives from l-serine for anti-tumour testing, see: Pinheiro et al. (2010 ▶, 2011a ▶,b ▶); de Souza et al. (2010 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C18H18ClN3O4

M = 375.80

Triclinic,

a = 4.6804 (4) Å

b = 5.6037 (7) Å

c = 16.946 (2) Å

α = 95.669 (6)°

β = 95.886 (7)°

γ = 94.467 (6)°

V = 438.20 (8) Å3

Z = 1

Mo Kα radiation

μ = 0.25 mm−1

T = 120 K

0.12 × 0.03 × 0.02 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.682, T max = 1.000

6351 measured reflections

3438 independent reflections

2520 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.196

S = 1.10

3438 reflections

244 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 1476 Friedel pairs

Flack parameter: 0.15 (12)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024895/hb5927sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024895/hb5927Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024895/hb5927Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18ClN3O4	Z = 1
Mr = 375.80	F(000) = 196
Triclinic, P1	Dx = 1.424 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6804 (4) Å	Cell parameters from 13950 reflections
b = 5.6037 (7) Å	θ = 2.9–27.5°
c = 16.946 (2) Å	µ = 0.25 mm−1
α = 95.669 (6)°	T = 120 K
β = 95.886 (7)°	Needle, yellow
γ = 94.467 (6)°	0.12 × 0.03 × 0.02 mm
V = 438.20 (8) Å3

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	3438 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2520 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.7°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −7→7
Tmin = 0.682, Tmax = 1.000	l = −21→21
6351 measured reflections

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)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.196	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3438 reflections	Δρmax = 0.38 e Å−3
244 parameters	Δρmin = −0.39 e Å−3
6 restraints	Absolute structure: Flack (1983), 1476 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.15 (12)

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

	x	y	z	Uiso*/Ueq
Cl	1.3824 (2)	1.3694 (2)	0.28152 (10)	0.0301 (4)
O1	0.5726 (7)	0.6300 (8)	0.4667 (3)	0.0298 (10)
O2	1.2666 (8)	0.1671 (7)	0.5712 (3)	0.0270 (10)
H2O	1.181 (14)	0.079 (11)	0.600 (4)	0.041*
O3	0.9314 (8)	0.8947 (7)	0.6569 (2)	0.0273 (10)
O4	0.5835 (8)	0.6630 (7)	0.7041 (2)	0.0265 (9)
N1	0.8863 (9)	0.7934 (8)	0.3539 (3)	0.0198 (10)
N2	1.0058 (10)	0.6984 (9)	0.4208 (3)	0.0221 (10)
H2N	1.195 (3)	0.713 (11)	0.429 (4)	0.026*
N3	0.8117 (10)	0.4981 (8)	0.6072 (3)	0.0230 (11)
H3N	0.683 (10)	0.377 (7)	0.610 (4)	0.028*
C1	0.9669 (12)	0.9974 (11)	0.2410 (4)	0.0233 (13)
C2	1.1001 (11)	1.2101 (10)	0.2184 (4)	0.0248 (13)
C3	0.9976 (13)	1.3025 (11)	0.1494 (4)	0.0287 (14)
H3	1.0844	1.4498	0.1359	0.034*
C4	0.7682 (13)	1.1799 (12)	0.1000 (4)	0.0315 (15)
H4	0.6996	1.2419	0.0521	0.038*
C5	0.6399 (13)	0.9705 (12)	0.1198 (4)	0.0308 (15)
H5	0.4842	0.8866	0.0851	0.037*
C6	0.7337 (12)	0.8786 (11)	0.1900 (3)	0.0228 (12)
H6	0.6394	0.7344	0.2035	0.027*
C7	1.0712 (12)	0.9037 (10)	0.3152 (3)	0.0223 (12)
H7	1.2704	0.9233	0.3345	0.027*
C8	0.8341 (11)	0.6206 (10)	0.4736 (3)	0.0212 (12)
C9	0.9896 (11)	0.5108 (10)	0.5429 (3)	0.0207 (12)
H9	1.1710	0.6148	0.5629	0.025*
C10	1.0689 (11)	0.2567 (11)	0.5148 (3)	0.0218 (12)
H10A	0.8910	0.1454	0.5048	0.026*
H10B	1.1540	0.2613	0.4638	0.026*
C11	0.7900 (11)	0.7019 (10)	0.6551 (3)	0.0190 (11)
C12	0.5549 (12)	0.8631 (11)	0.7614 (3)	0.0236 (13)
H12A	0.4789	0.9962	0.7337	0.028*
H12B	0.7465	0.9217	0.7900	0.028*
C13	0.3567 (11)	0.7911 (11)	0.8197 (4)	0.0244 (13)
C14	0.2025 (12)	0.5668 (11)	0.8127 (4)	0.0286 (14)
H14	0.2219	0.4510	0.7691	0.034*
C15	0.0196 (14)	0.5110 (13)	0.8693 (5)	0.0373 (16)
H15	−0.0830	0.3563	0.8648	0.045*
C16	−0.0126 (13)	0.6770 (13)	0.9310 (4)	0.0363 (16)
H16	−0.1406	0.6383	0.9688	0.044*
C17	0.1389 (13)	0.9020 (13)	0.9394 (4)	0.0336 (15)
H17	0.1162	1.0166	0.9830	0.040*
C18	0.3217 (12)	0.9584 (11)	0.8845 (4)	0.0275 (13)
H18	0.4261	1.1127	0.8903	0.033*

	U11	U22	U33	U12	U13	U23
Cl	0.0278 (7)	0.0258 (8)	0.0367 (9)	0.0003 (6)	0.0059 (6)	0.0024 (6)
O1	0.017 (2)	0.048 (3)	0.029 (2)	0.0077 (19)	0.0078 (17)	0.016 (2)
O2	0.025 (2)	0.025 (2)	0.034 (3)	0.0034 (18)	0.0036 (18)	0.0113 (19)
O3	0.025 (2)	0.028 (2)	0.028 (2)	−0.0022 (18)	0.0054 (17)	−0.0004 (18)
O4	0.024 (2)	0.031 (2)	0.023 (2)	−0.0005 (18)	0.0069 (17)	−0.0022 (17)
N1	0.020 (2)	0.020 (2)	0.018 (2)	0.0046 (19)	−0.0017 (18)	0.001 (2)
N2	0.017 (2)	0.027 (3)	0.022 (3)	0.0034 (19)	0.0024 (19)	0.005 (2)
N3	0.019 (2)	0.023 (3)	0.028 (3)	−0.0027 (19)	0.008 (2)	0.004 (2)
C1	0.022 (3)	0.029 (3)	0.022 (3)	0.008 (2)	0.009 (2)	0.002 (3)
C2	0.022 (3)	0.028 (3)	0.025 (3)	0.008 (2)	0.008 (2)	−0.007 (3)
C3	0.034 (3)	0.027 (3)	0.031 (3)	0.007 (3)	0.016 (3)	0.012 (3)
C4	0.036 (3)	0.044 (4)	0.017 (3)	0.009 (3)	0.006 (3)	0.010 (3)
C5	0.028 (3)	0.040 (4)	0.025 (3)	0.005 (3)	0.004 (3)	0.004 (3)
C6	0.022 (3)	0.025 (3)	0.023 (3)	0.007 (2)	0.001 (2)	0.009 (2)
C7	0.020 (3)	0.020 (3)	0.025 (3)	0.001 (2)	0.002 (2)	0.001 (2)
C8	0.012 (2)	0.023 (3)	0.027 (3)	−0.001 (2)	0.004 (2)	0.000 (2)
C9	0.015 (2)	0.026 (3)	0.020 (3)	−0.001 (2)	0.001 (2)	0.002 (2)
C10	0.019 (3)	0.028 (3)	0.018 (3)	0.002 (2)	0.002 (2)	0.000 (2)
C11	0.012 (2)	0.027 (3)	0.019 (3)	0.003 (2)	0.004 (2)	0.004 (2)
C12	0.021 (3)	0.029 (3)	0.022 (3)	0.005 (2)	0.005 (2)	0.001 (2)
C13	0.014 (3)	0.035 (3)	0.025 (3)	0.012 (2)	0.003 (2)	0.001 (3)
C14	0.024 (3)	0.035 (4)	0.030 (3)	0.012 (3)	0.008 (3)	0.000 (3)
C15	0.027 (3)	0.035 (4)	0.053 (4)	0.003 (3)	0.013 (3)	0.014 (3)
C16	0.031 (3)	0.053 (4)	0.032 (4)	0.019 (3)	0.014 (3)	0.015 (3)
C17	0.027 (3)	0.047 (4)	0.026 (3)	0.011 (3)	0.003 (3)	−0.003 (3)
C18	0.021 (3)	0.032 (3)	0.028 (3)	0.001 (3)	0.003 (2)	0.000 (3)

Cl—C2	1.739 (6)	C5—H5	0.9500
O1—C8	1.223 (6)	C6—H6	0.9500
O2—C10	1.417 (7)	C7—H7	0.9500
O2—H2O	0.842 (10)	C8—C9	1.525 (8)
O3—C11	1.218 (7)	C9—C10	1.541 (8)
O4—C11	1.357 (6)	C9—H9	1.0000
O4—C12	1.433 (6)	C10—H10A	0.9900
N1—C7	1.294 (7)	C10—H10B	0.9900
N1—N2	1.385 (6)	C12—C13	1.485 (8)
N2—C8	1.343 (7)	C12—H12A	0.9900
N2—H2N	0.877 (10)	C12—H12B	0.9900
N3—C11	1.351 (7)	C13—C14	1.388 (9)
N3—C9	1.441 (7)	C13—C18	1.403 (8)
N3—H3N	0.878 (10)	C14—C15	1.391 (9)
C1—C6	1.400 (8)	C14—H14	0.9500
C1—C2	1.407 (8)	C15—C16	1.357 (10)
C1—C7	1.462 (8)	C15—H15	0.9500
C2—C3	1.381 (8)	C16—C17	1.385 (10)
C3—C4	1.383 (9)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.371 (8)
C4—C5	1.364 (9)	C17—H17	0.9500
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.386 (9)
C10—O2—H2O	111 (5)	N3—C9—H9	108.7
C11—O4—C12	114.7 (4)	C8—C9—H9	108.7
C7—N1—N2	114.6 (4)	C10—C9—H9	108.7
C8—N2—N1	119.6 (4)	O2—C10—C9	112.6 (4)
C8—N2—H2N	124 (4)	O2—C10—H10A	109.1
N1—N2—H2N	115 (4)	C9—C10—H10A	109.1
C11—N3—C9	118.3 (5)	O2—C10—H10B	109.1
C11—N3—H3N	117 (4)	C9—C10—H10B	109.1
C9—N3—H3N	123 (4)	H10A—C10—H10B	107.8
C6—C1—C2	117.8 (5)	O3—C11—N3	127.3 (5)
C6—C1—C7	121.4 (5)	O3—C11—O4	122.9 (5)
C2—C1—C7	120.7 (5)	N3—C11—O4	109.8 (5)
C3—C2—C1	120.9 (5)	O4—C12—C13	110.4 (5)
C3—C2—Cl	119.5 (5)	O4—C12—H12A	109.6
C1—C2—Cl	119.4 (5)	C13—C12—H12A	109.6
C2—C3—C4	119.8 (6)	O4—C12—H12B	109.6
C2—C3—H3	120.1	C13—C12—H12B	109.6
C4—C3—H3	120.1	H12A—C12—H12B	108.1
C5—C4—C3	120.3 (6)	C14—C13—C18	118.4 (5)
C5—C4—H4	119.9	C14—C13—C12	123.1 (5)
C3—C4—H4	119.9	C18—C13—C12	118.5 (5)
C4—C5—C6	120.8 (6)	C13—C14—C15	120.2 (6)
C4—C5—H5	119.6	C13—C14—H14	119.9
C6—C5—H5	119.6	C15—C14—H14	119.9
C5—C6—C1	120.3 (6)	C16—C15—C14	120.2 (7)
C5—C6—H6	119.9	C16—C15—H15	119.9
C1—C6—H6	119.9	C14—C15—H15	119.9
N1—C7—C1	118.5 (5)	C15—C16—C17	120.8 (6)
N1—C7—H7	120.7	C15—C16—H16	119.6
C1—C7—H7	120.7	C17—C16—H16	119.6
O1—C8—N2	123.7 (5)	C18—C17—C16	119.6 (6)
O1—C8—C9	121.7 (5)	C18—C17—H17	120.2
N2—C8—C9	114.6 (4)	C16—C17—H17	120.2
N3—C9—C8	110.6 (4)	C17—C18—C13	120.8 (6)
N3—C9—C10	109.7 (5)	C17—C18—H18	119.6
C8—C9—C10	110.2 (5)	C13—C18—H18	119.6
C7—N1—N2—C8	167.6 (5)	N2—C8—C9—N3	163.1 (5)
C6—C1—C2—C3	2.1 (8)	O1—C8—C9—C10	102.9 (6)
C7—C1—C2—C3	−178.3 (5)	N2—C8—C9—C10	−75.4 (6)
C6—C1—C2—Cl	177.8 (4)	N3—C9—C10—O2	−70.8 (5)
C7—C1—C2—Cl	−2.6 (7)	C8—C9—C10—O2	167.1 (4)
C1—C2—C3—C4	−2.6 (8)	C9—N3—C11—O3	−9.6 (8)
Cl—C2—C3—C4	−178.3 (5)	C9—N3—C11—O4	171.2 (5)
C2—C3—C4—C5	1.1 (9)	C12—O4—C11—O3	−3.2 (7)
C3—C4—C5—C6	0.9 (10)	C12—O4—C11—N3	176.0 (4)
C4—C5—C6—C1	−1.4 (9)	C11—O4—C12—C13	−171.5 (5)
C2—C1—C6—C5	−0.1 (8)	O4—C12—C13—C14	−6.0 (7)
C7—C1—C6—C5	−179.7 (5)	O4—C12—C13—C18	174.6 (5)
N2—N1—C7—C1	176.4 (5)	C18—C13—C14—C15	−0.4 (8)
C6—C1—C7—N1	−33.8 (8)	C12—C13—C14—C15	−179.8 (6)
C2—C1—C7—N1	146.7 (5)	C13—C14—C15—C16	1.0 (10)
N1—N2—C8—O1	−0.6 (8)	C14—C15—C16—C17	−1.1 (10)
N1—N2—C8—C9	177.6 (5)	C15—C16—C17—C18	0.5 (10)
C11—N3—C9—C8	−77.4 (6)	C16—C17—C18—C13	0.2 (9)
C11—N3—C9—C10	160.8 (5)	C14—C13—C18—C17	−0.2 (8)
O1—C8—C9—N3	−18.6 (7)	C12—C13—C18—C17	179.3 (5)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O3i	0.84 (8)	1.89 (9)	2.728 (7)	171 (9)
N3—H3n···O2ii	0.88 (6)	2.20 (6)	3.006 (8)	153 (7)
N2—H2n···O1iii	0.88 (3)	1.93 (4)	2.758 (8)	158 (7)
C6—H6···Cliv	0.95	2.81	3.734 (8)	166
C12—H12b···Cg1iii	0.99	2.69	3.474 (8)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O3i	0.84 (8)	1.89 (9)	2.728 (7)	171 (9)
N3—H3n⋯O2ii	0.88 (6)	2.20 (6)	3.006 (8)	153 (7)
N2—H2n⋯O1iii	0.88 (3)	1.93 (4)	2.758 (8)	158 (7)
C6—H6⋯Cliv	0.95	2.81	3.734 (8)	166
C12—H12b⋯Cg1iii	0.99	2.69	3.474 (8)	137

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