Benzyl N-((S)-2-hydr-oxy-1-{N'-[(E)-2-methoxy-benzyl-idene]hydrazinecarbon-yl}eth-yl)carbamate from synchrotron data.

A U-shaped conformation is found in the title compound, C(19)H(21)N(3)O(5), with the benzene rings lying to the same side of the mol-ecule; the dihedral angle between them is 10.83 (16)°. The dihedral angle formed between the hydrazinecarbonyl and carbamate residues is 68.42 (13)°. The carbonyl groups lie approximately at right angles to each other [O-C⋯C-O pseudo torsion angle of 107.7 (3)°], and the conformation about the C12=N3 bond [1.279 (4) Å] is E. An intra-molecular N(cb)-H⋯O(hy) (cb = carbmate and hy = hydr-oxy) hydrogen bond occurs, generating an S(6) loop. In the crystal, inter-molecular O(h)-H⋯O(ca) (ca = carbon-yl) and N(hz)-H⋯O(ca) (hz = hydrazine) hydrogen bonds lead to the formation of a supra-molecular chain, two mol-ecules thick, which propagates along the a axis; these are connected by C-H⋯O(ca) contacts.

Related literature

For background to tuberculosis, see: Cole & Alzari (2007 ▶); Portero & Rubio (2007 ▶). For information on the development of anti-tuberculosis agents, see: Lourenço et al. (2007a ▶,b ▶); Lourenço et al. (2008 ▶); Ferreira et al. (2008 ▶); Costa et al. (2006 ▶); de Souza et al. (2006a ▶,b ▶); Pinheiro et al. (2007 ▶).

Experimental

Crystal data

C19H21N3O5

M = 371.39

Orthorhombic,

a = 6.002 (6) Å

b = 14.053 (14) Å

c = 21.09 (2) Å

V = 1779 (3) Å3

Z = 4

Synchrotron radiation

λ = 0.6889 Å

μ = 0.06 mm−1

T = 120 K

0.30 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn 724+ detector on Crystal Logics CCD diffractometer

13639 measured reflections

1827 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.124

S = 1.29

1827 reflections

257 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: APEX2 (Bruker, 2008 ▶); data reduction: APEX2; 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 datablocks global, I. DOI: 10.1107/S1600536810011463/hb5379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011463/hb5379Isup2.hkl

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

C19H21N3O5	F(000) = 784
Mr = 371.39	Dx = 1.387 Mg m−3
Orthorhombic, P212121	Synchrotron radiation, λ = 0.6889 Å
Hall symbol: P 2ac 2ab	Cell parameters from 915 reflections
a = 6.002 (6) Å	θ = 3.1–23.8°
b = 14.053 (14) Å	µ = 0.06 mm−1
c = 21.09 (2) Å	T = 120 K
V = 1779 (3) Å3	Needle, colourless
Z = 4	0.30 × 0.04 × 0.02 mm

Rigaku Saturn 724+ detector on Crystal Logics CCD diffractometer	1627 reflections with I > 2σ(I)
Radiation source: Diamond beamline I19	Rint = 0.047
silicon double crystal	θmax = 24.3°, θmin = 1.7°
ω scans	h = −5→7
13639 measured reflections	k = −16→16
1827 independent reflections	l = −25→25

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0788P)2] where P = (Fo2 + 2Fc2)/3
S = 1.29	(Δ/σ)max = 0.001
1827 reflections	Δρmax = 0.22 e Å−3
257 parameters	Δρmin = −0.31 e Å−3
3 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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
O1	0.8873 (4)	−0.04357 (14)	0.54989 (10)	0.0315 (5)
O2	0.8048 (4)	0.11402 (14)	0.55153 (10)	0.0300 (5)
O3	1.4014 (4)	0.06852 (18)	0.39880 (12)	0.0386 (6)
H3O	1.531 (3)	0.068 (3)	0.3838 (18)	0.039 (11)*
O4	0.8614 (4)	0.09631 (14)	0.39964 (10)	0.0281 (5)
O5	0.8039 (4)	0.54912 (16)	0.29894 (11)	0.0360 (6)
N1	1.1190 (5)	0.05803 (18)	0.50353 (12)	0.0275 (6)
H1N	1.161 (6)	0.0066 (16)	0.4822 (15)	0.043 (11)*
N2	0.9615 (5)	0.25280 (17)	0.39885 (12)	0.0279 (6)
H2N	1.059 (5)	0.294 (2)	0.4132 (18)	0.054 (12)*
N3	0.7903 (5)	0.27845 (18)	0.35818 (12)	0.0278 (6)
C1	0.6559 (6)	−0.1678 (2)	0.59051 (15)	0.0314 (8)
C2	0.8207 (7)	−0.2227 (2)	0.61849 (16)	0.0369 (8)
H2	0.9550	−0.1935	0.6322	0.044*
C3	0.7916 (7)	−0.3195 (2)	0.62669 (17)	0.0404 (9)
H3	0.9057	−0.3568	0.6456	0.048*
C4	0.5939 (7)	−0.3618 (2)	0.60700 (16)	0.0415 (9)
H4	0.5718	−0.4281	0.6132	0.050*
C5	0.4302 (8)	−0.3084 (3)	0.57863 (18)	0.0443 (9)
H5	0.2961	−0.3378	0.5649	0.053*
C6	0.4612 (7)	−0.2106 (2)	0.57000 (17)	0.0384 (9)
H6	0.3487	−0.1735	0.5501	0.046*
C7	0.6851 (6)	−0.0622 (2)	0.58501 (16)	0.0333 (8)
H7A	0.5558	−0.0340	0.5627	0.040*
H7B	0.6949	−0.0333	0.6277	0.040*
C8	0.9259 (6)	0.0482 (2)	0.53586 (14)	0.0271 (7)
C9	1.1576 (5)	0.1469 (2)	0.46987 (14)	0.0256 (7)
H9	1.1481	0.2004	0.5010	0.031*
C10	1.3898 (6)	0.1464 (2)	0.44118 (14)	0.0282 (7)
H10A	1.4175	0.2067	0.4182	0.034*
H10B	1.5034	0.1397	0.4749	0.034*
C11	0.9775 (5)	0.1615 (2)	0.41900 (14)	0.0247 (7)
C12	0.7823 (6)	0.3673 (2)	0.34522 (14)	0.0281 (7)
H12	0.8937	0.4088	0.3614	0.034*
C13	0.6034 (6)	0.4056 (2)	0.30579 (14)	0.0290 (7)
C14	0.6157 (6)	0.4991 (2)	0.28244 (14)	0.0296 (8)
C15	0.4450 (6)	0.5358 (2)	0.24549 (15)	0.0323 (8)
H15	0.4531	0.5995	0.2304	0.039*
C16	0.2632 (7)	0.4798 (2)	0.23060 (15)	0.0339 (8)
H16	0.1477	0.5046	0.2046	0.041*
C17	0.2486 (6)	0.3872 (2)	0.25348 (15)	0.0318 (8)
H17	0.1230	0.3490	0.2434	0.038*
C18	0.4166 (6)	0.3511 (2)	0.29081 (15)	0.0312 (7)
H18	0.4050	0.2880	0.3066	0.037*
C19	0.8395 (7)	0.6391 (2)	0.26835 (16)	0.0374 (9)
H19A	0.7233	0.6839	0.2815	0.056*
H19B	0.8337	0.6306	0.2223	0.056*
H19C	0.9858	0.6641	0.2804	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0299 (14)	0.0250 (10)	0.0396 (12)	0.0018 (10)	0.0069 (11)	0.0038 (9)
O2	0.0292 (14)	0.0283 (11)	0.0326 (11)	0.0038 (10)	0.0030 (10)	−0.0003 (9)
O3	0.0262 (14)	0.0436 (13)	0.0461 (14)	−0.0025 (12)	0.0049 (13)	−0.0140 (11)
O4	0.0239 (14)	0.0278 (11)	0.0327 (11)	−0.0005 (10)	−0.0004 (10)	−0.0024 (9)
O5	0.0347 (14)	0.0299 (11)	0.0434 (13)	−0.0050 (11)	−0.0073 (12)	0.0092 (10)
N1	0.0284 (16)	0.0246 (12)	0.0295 (13)	0.0034 (12)	0.0014 (12)	0.0013 (10)
N2	0.0260 (17)	0.0252 (12)	0.0327 (13)	−0.0009 (12)	−0.0040 (12)	0.0012 (11)
N3	0.0242 (16)	0.0296 (13)	0.0295 (13)	−0.0002 (12)	−0.0019 (12)	0.0016 (10)
C1	0.031 (2)	0.0318 (16)	0.0311 (16)	0.0001 (15)	0.0046 (15)	0.0005 (13)
C2	0.034 (2)	0.0339 (17)	0.0430 (19)	0.0008 (16)	−0.0002 (17)	0.0041 (14)
C3	0.047 (2)	0.0321 (17)	0.0424 (19)	0.0056 (18)	0.0049 (18)	0.0059 (14)
C4	0.055 (3)	0.0294 (15)	0.0401 (18)	−0.0052 (18)	0.015 (2)	−0.0022 (13)
C5	0.044 (3)	0.0455 (19)	0.0435 (19)	−0.0143 (19)	0.0070 (19)	−0.0070 (15)
C6	0.037 (2)	0.0412 (18)	0.0372 (17)	−0.0010 (17)	0.0012 (16)	−0.0022 (15)
C7	0.029 (2)	0.0308 (16)	0.0404 (17)	0.0017 (15)	0.0068 (15)	0.0038 (13)
C8	0.0267 (19)	0.0278 (14)	0.0267 (15)	0.0000 (14)	−0.0030 (14)	0.0017 (12)
C9	0.0244 (18)	0.0243 (14)	0.0280 (15)	0.0013 (13)	0.0010 (14)	0.0007 (11)
C10	0.0267 (19)	0.0255 (14)	0.0324 (16)	−0.0028 (14)	−0.0011 (15)	−0.0005 (12)
C11	0.0203 (18)	0.0259 (14)	0.0279 (15)	−0.0001 (13)	0.0049 (13)	−0.0016 (12)
C12	0.0253 (19)	0.0296 (15)	0.0293 (15)	−0.0038 (14)	−0.0002 (14)	0.0004 (13)
C13	0.031 (2)	0.0296 (15)	0.0265 (15)	0.0030 (15)	−0.0002 (14)	−0.0006 (12)
C14	0.029 (2)	0.0302 (16)	0.0292 (15)	0.0012 (15)	−0.0005 (15)	0.0000 (12)
C15	0.037 (2)	0.0302 (16)	0.0294 (16)	0.0028 (16)	0.0015 (16)	0.0041 (12)
C16	0.034 (2)	0.0364 (18)	0.0309 (17)	0.0069 (16)	−0.0039 (16)	−0.0018 (13)
C17	0.028 (2)	0.0342 (17)	0.0328 (17)	0.0017 (14)	−0.0030 (15)	−0.0018 (13)
C18	0.033 (2)	0.0296 (15)	0.0308 (15)	−0.0004 (16)	−0.0001 (15)	0.0013 (12)
C19	0.044 (2)	0.0275 (16)	0.0410 (18)	−0.0027 (16)	−0.0028 (17)	0.0091 (13)

O1—C8	1.343 (4)	C5—H5	0.9500
O1—C7	1.446 (4)	C6—H6	0.9500
O2—C8	1.222 (4)	C7—H7A	0.9900
O3—C10	1.415 (4)	C7—H7B	0.9900
O3—H3O	0.843 (11)	C9—C10	1.519 (5)
O4—C11	1.221 (4)	C9—C11	1.537 (4)
O5—C14	1.375 (4)	C9—H9	1.0000
O5—C19	1.435 (4)	C10—H10A	0.9900
N1—C8	1.352 (5)	C10—H10B	0.9900
N1—C9	1.455 (4)	C12—C13	1.461 (5)
N1—H1N	0.89 (3)	C12—H12	0.9500
N2—C11	1.355 (4)	C13—C18	1.394 (5)
N2—N3	1.386 (4)	C13—C14	1.405 (4)
N2—H2N	0.88 (3)	C14—C15	1.386 (5)
N3—C12	1.279 (4)	C15—C16	1.382 (5)
C1—C6	1.383 (5)	C15—H15	0.9500
C1—C2	1.386 (5)	C16—C17	1.390 (5)
C1—C7	1.499 (5)	C16—H16	0.9500
C2—C3	1.383 (5)	C17—C18	1.376 (5)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.391 (6)	C18—H18	0.9500
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.374 (6)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.399 (5)
C8—O1—C7	115.6 (2)	N1—C9—H9	108.5
C10—O3—H3O	107 (3)	C10—C9—H9	108.5
C14—O5—C19	117.3 (3)	C11—C9—H9	108.5
C8—N1—C9	118.1 (3)	O3—C10—C9	107.5 (3)
C8—N1—H1N	115 (3)	O3—C10—H10A	110.2
C9—N1—H1N	114 (2)	C9—C10—H10A	110.2
C11—N2—N3	119.5 (3)	O3—C10—H10B	110.2
C11—N2—H2N	118 (3)	C9—C10—H10B	110.2
N3—N2—H2N	122 (3)	H10A—C10—H10B	108.5
C12—N3—N2	114.4 (3)	O4—C11—N2	124.4 (3)
C6—C1—C2	119.6 (3)	O4—C11—C9	122.3 (3)
C6—C1—C7	120.3 (3)	N2—C11—C9	113.3 (3)
C2—C1—C7	120.1 (3)	N3—C12—C13	120.6 (3)
C3—C2—C1	120.7 (4)	N3—C12—H12	119.7
C3—C2—H2	119.6	C13—C12—H12	119.7
C1—C2—H2	119.6	C18—C13—C14	118.5 (3)
C2—C3—C4	119.4 (4)	C18—C13—C12	121.2 (3)
C2—C3—H3	120.3	C14—C13—C12	120.3 (3)
C4—C3—H3	120.3	O5—C14—C15	124.0 (3)
C5—C4—C3	120.4 (3)	O5—C14—C13	115.6 (3)
C5—C4—H4	119.8	C15—C14—C13	120.4 (3)
C3—C4—H4	119.8	C16—C15—C14	119.9 (3)
C4—C5—C6	119.9 (4)	C16—C15—H15	120.0
C4—C5—H5	120.0	C14—C15—H15	120.0
C6—C5—H5	120.0	C15—C16—C17	120.3 (3)
C1—C6—C5	119.9 (4)	C15—C16—H16	119.9
C1—C6—H6	120.1	C17—C16—H16	119.9
C5—C6—H6	120.1	C18—C17—C16	119.8 (3)
O1—C7—C1	108.5 (3)	C18—C17—H17	120.1
O1—C7—H7A	110.0	C16—C17—H17	120.1
C1—C7—H7A	110.0	C17—C18—C13	121.1 (3)
O1—C7—H7B	110.0	C17—C18—H18	119.5
C1—C7—H7B	110.0	C13—C18—H18	119.5
H7A—C7—H7B	108.4	O5—C19—H19A	109.5
O2—C8—O1	124.4 (3)	O5—C19—H19B	109.5
O2—C8—N1	124.7 (3)	H19A—C19—H19B	109.5
O1—C8—N1	110.9 (3)	O5—C19—H19C	109.5
N1—C9—C10	109.7 (3)	H19A—C19—H19C	109.5
N1—C9—C11	110.1 (3)	H19B—C19—H19C	109.5
C10—C9—C11	111.6 (2)
C11—N2—N3—C12	175.9 (3)	N3—N2—C11—C9	−173.0 (2)
C6—C1—C2—C3	−0.6 (5)	N1—C9—C11—O4	−18.0 (4)
C7—C1—C2—C3	176.8 (3)	C10—C9—C11—O4	104.0 (3)
C1—C2—C3—C4	−0.5 (5)	N1—C9—C11—N2	161.6 (3)
C2—C3—C4—C5	1.2 (5)	C10—C9—C11—N2	−76.3 (3)
C3—C4—C5—C6	−0.7 (5)	N2—N3—C12—C13	−176.6 (3)
C2—C1—C6—C5	1.1 (5)	N3—C12—C13—C18	11.7 (5)
C7—C1—C6—C5	−176.3 (3)	N3—C12—C13—C14	−168.8 (3)
C4—C5—C6—C1	−0.5 (5)	C19—O5—C14—C15	−9.5 (5)
C8—O1—C7—C1	174.1 (3)	C19—O5—C14—C13	170.7 (3)
C6—C1—C7—O1	−124.9 (3)	C18—C13—C14—O5	180.0 (3)
C2—C1—C7—O1	57.7 (4)	C12—C13—C14—O5	0.4 (4)
C7—O1—C8—O2	1.1 (4)	C18—C13—C14—C15	0.1 (5)
C7—O1—C8—N1	179.6 (3)	C12—C13—C14—C15	−179.4 (3)
C9—N1—C8—O2	−17.9 (4)	O5—C14—C15—C16	179.1 (3)
C9—N1—C8—O1	163.6 (3)	C13—C14—C15—C16	−1.1 (5)
C8—N1—C9—C10	175.6 (3)	C14—C15—C16—C17	1.2 (5)
C8—N1—C9—C11	−61.2 (3)	C15—C16—C17—C18	−0.4 (5)
N1—C9—C10—O3	60.0 (3)	C16—C17—C18—C13	−0.6 (5)
C11—C9—C10—O3	−62.3 (3)	C14—C13—C18—C17	0.7 (5)
N3—N2—C11—O4	6.6 (5)	C12—C13—C18—C17	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3	0.89 (3)	2.44 (3)	2.788 (5)	104 (2)
O3—H3o···O4i	0.85 (2)	2.04 (2)	2.789 (4)	147 (4)
N2—H2n···O2ii	0.88 (3)	2.10 (3)	2.974 (5)	177 (3)
C10—H10b···O2i	0.99	2.45	3.439 (5)	175
C16—H16···O4iii	0.95	2.55	3.284 (5)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3	0.89 (3)	2.44 (3)	2.788 (5)	104 (2)
O3—H3o⋯O4i	0.85 (2)	2.04 (2)	2.789 (4)	147 (4)
N2—H2n⋯O2ii	0.88 (3)	2.10 (3)	2.974 (5)	177 (3)
C10—H10b⋯O2i	0.99	2.45	3.439 (5)	175
C16—H16⋯O4iii	0.95	2.55	3.284 (5)	134

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