Literature DB >> 21583900

Methyl N'-[(E)-2-methoxy-benzyl-idene]-hydrazinecarboxyl-ate.

Lu-Ping Lv, Wen-Bo Yu, Zhong-Hao Lu, Wei-Wei Li, Xian-Chao Hu.

Abstract

The title compound, C(10)H(12)N(2)O(3), crystallizes with two independent mol-ecules in the asymmetric unit. The side chains in the two independent mol-ecules have slightly different orientations, with the C=N-N-C torsion angle being 169.19 (14)° in one of the mol-ecules and -179.86 (14)° in the other. Each independent mol-ecule adopts a trans configuration with respect to the C=N bond. In the crystal structure, mol-ecules are linked into chains running along [001] by N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds. In addition, an inter-molecular C-H⋯π inter-action is observed.

Entities: Chemical Disease Species

Year: 2009 PMID： 21583900 PMCID： PMC2977764 DOI： 10.1107/S1600536809014172

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For applications of benzaldehydehydrazone derviatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For n class="Chemical">metal complexes of Schiff base ligands, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For a related structure, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C10H12N2O3 M = 208.22 Monoclinic, a = 17.221 (5) Å b = 7.442 (2) Å c = 16.611 (6) Å β = 95.423 (12)° V = 2119.4 (12) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 223 K 0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.977, T max = 0.989 11064 measured reflections 3723 independent reflections 2834 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.120 S = 1.08 3723 reflections 271 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.18 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014172/ci2777sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014172/ci2777Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₁₂N₂O₃	F(000) = 880
M_r = 208.22	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3723 reflections
a = 17.221 (5) Å	θ = 1.2–25.0°
b = 7.442 (2) Å	µ = 0.10 mm⁻¹
c = 16.611 (6) Å	T = 223 K
β = 95.423 (12)°	Block, colourless
V = 2119.4 (12) Å³	0.24 × 0.21 × 0.19 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3723 independent reflections
Radiation source: fine-focus sealed tube	2834 reflections with I > 2σ(I)
graphite	R_int = 0.026
φ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −20→20
T_min = 0.977, T_max = 0.989	k = −8→8
11064 measured reflections	l = −19→18

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0639P)² + 0.1492P] where P = (F_o² + 2F_c²)/3
3723 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
O1	0.27964 (7)	−0.12236 (16)	0.66716 (7)	0.0579 (3)
O3	0.41712 (7)	0.63135 (17)	0.50573 (7)	0.0644 (4)
O2	0.36311 (7)	0.49059 (17)	0.39394 (7)	0.0649 (4)
O6	0.45355 (6)	0.3646 (2)	0.82317 (7)	0.0676 (4)
O4	0.06692 (7)	0.15183 (19)	0.84498 (9)	0.0716 (4)
N3	0.26187 (7)	0.29235 (18)	0.74487 (8)	0.0478 (3)
O5	0.40316 (7)	0.3884 (2)	0.69432 (8)	0.0733 (4)
N1	0.31881 (7)	0.21928 (19)	0.49137 (8)	0.0483 (3)
N2	0.35854 (8)	0.37207 (19)	0.51936 (8)	0.0522 (4)
H2N	0.3707	0.3869	0.5703	0.063*
N4	0.32825 (7)	0.3208 (2)	0.79597 (8)	0.0525 (4)
H4N	0.3270	0.3140	0.8475	0.063*
C7	0.26100 (8)	−0.0607 (2)	0.52867 (9)	0.0460 (4)
C17	0.13105 (9)	0.1853 (2)	0.72717 (11)	0.0506 (4)
C18	0.20343 (9)	0.2284 (2)	0.77764 (10)	0.0497 (4)
H18	0.2067	0.2093	0.8332	0.060*
C8	0.30274 (8)	0.1085 (2)	0.54641 (10)	0.0479 (4)
H8	0.3183	0.1366	0.6001	0.057*
C9	0.37808 (9)	0.4974 (2)	0.46625 (10)	0.0492 (4)
C16	0.12959 (10)	0.1783 (3)	0.64363 (12)	0.0616 (5)
H16	0.1746	0.2063	0.6194	0.074*
C4	0.18349 (10)	−0.3883 (3)	0.50054 (12)	0.0635 (5)
H4	0.1581	−0.4976	0.4910	0.076*
C3	0.21174 (10)	−0.3421 (2)	0.57816 (11)	0.0569 (5)
H3	0.2052	−0.4199	0.6208	0.068*
C5	0.19269 (10)	−0.2740 (3)	0.43723 (11)	0.0630 (5)
H5	0.1730	−0.3054	0.3851	0.076*
C1	0.26395 (13)	−0.2246 (3)	0.73518 (11)	0.0735 (6)
H1A	0.2882	−0.1691	0.7833	0.110*
H1B	0.2843	−0.3438	0.7304	0.110*
H1C	0.2086	−0.2306	0.7382	0.110*
C2	0.25007 (8)	−0.1791 (2)	0.59263 (10)	0.0470 (4)
C20	0.53167 (10)	0.3890 (3)	0.80043 (15)	0.0834 (7)
H20A	0.5678	0.3901	0.8481	0.125*
H20B	0.5348	0.5010	0.7722	0.125*
H20C	0.5444	0.2922	0.7658	0.125*
C10	0.44366 (12)	0.7734 (3)	0.45624 (14)	0.0771 (6)
H10A	0.4707	0.8621	0.4901	0.116*
H10B	0.3997	0.8279	0.4258	0.116*
H10C	0.4783	0.7247	0.4198	0.116*
C6	0.23130 (10)	−0.1116 (3)	0.45094 (11)	0.0578 (5)
H6	0.2375	−0.0354	0.4076	0.069*
C14	−0.00378 (13)	0.0922 (3)	0.63078 (16)	0.0853 (7)
H14	−0.0489	0.0620	0.5984	0.102*
C19	0.39555 (9)	0.3595 (2)	0.76374 (10)	0.0477 (4)
C13	−0.00495 (11)	0.0976 (3)	0.71332 (16)	0.0752 (6)
H13	−0.0507	0.0708	0.7365	0.090*
C12	0.06241 (9)	0.1433 (2)	0.76246 (12)	0.0582 (5)
C15	0.06312 (12)	0.1308 (3)	0.59552 (14)	0.0783 (6)
H15	0.0636	0.1250	0.5396	0.094*
C11	−0.00264 (13)	0.1165 (3)	0.88362 (16)	0.0942 (8)
H11A	0.0085	0.1268	0.9412	0.141*
H11B	−0.0208	−0.0028	0.8703	0.141*
H11C	−0.0422	0.2019	0.8652	0.141*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0726 (7)	0.0557 (8)	0.0444 (7)	−0.0051 (6)	0.0008 (5)	0.0033 (5)
O3	0.0752 (8)	0.0550 (8)	0.0625 (8)	−0.0139 (6)	0.0050 (6)	−0.0052 (6)
O2	0.0852 (8)	0.0594 (9)	0.0491 (8)	−0.0064 (6)	0.0008 (6)	0.0032 (6)
O6	0.0470 (6)	0.0963 (11)	0.0579 (8)	−0.0085 (6)	−0.0042 (5)	0.0026 (7)
O4	0.0582 (7)	0.0764 (10)	0.0818 (10)	−0.0074 (6)	0.0150 (6)	0.0087 (7)
N3	0.0471 (7)	0.0452 (8)	0.0496 (8)	0.0012 (6)	−0.0030 (6)	0.0025 (6)
O5	0.0682 (8)	0.1061 (12)	0.0457 (8)	−0.0207 (7)	0.0058 (6)	0.0028 (7)
N1	0.0514 (7)	0.0468 (9)	0.0464 (8)	0.0006 (6)	0.0027 (6)	−0.0005 (7)
N2	0.0624 (8)	0.0539 (10)	0.0392 (7)	−0.0041 (7)	−0.0002 (6)	−0.0016 (6)
N4	0.0462 (7)	0.0693 (10)	0.0408 (7)	−0.0045 (6)	−0.0018 (6)	0.0058 (7)
C7	0.0417 (8)	0.0506 (10)	0.0461 (9)	0.0046 (7)	0.0065 (6)	−0.0014 (8)
C17	0.0474 (8)	0.0382 (10)	0.0648 (11)	0.0069 (7)	−0.0018 (7)	−0.0028 (8)
C18	0.0489 (9)	0.0466 (10)	0.0528 (10)	0.0038 (7)	0.0009 (7)	0.0009 (8)
C8	0.0482 (8)	0.0540 (11)	0.0416 (9)	0.0036 (7)	0.0047 (7)	−0.0010 (8)
C9	0.0526 (9)	0.0483 (11)	0.0462 (10)	0.0050 (7)	0.0021 (7)	−0.0018 (8)
C16	0.0562 (10)	0.0587 (12)	0.0681 (12)	0.0111 (8)	−0.0036 (8)	−0.0107 (9)
C4	0.0579 (10)	0.0629 (13)	0.0704 (13)	−0.0092 (9)	0.0093 (9)	−0.0139 (10)
C3	0.0579 (10)	0.0535 (12)	0.0605 (11)	−0.0032 (8)	0.0110 (8)	0.0008 (9)
C5	0.0601 (10)	0.0758 (14)	0.0525 (11)	−0.0061 (9)	0.0012 (8)	−0.0149 (10)
C1	0.1031 (15)	0.0659 (14)	0.0504 (11)	−0.0079 (11)	0.0014 (10)	0.0094 (10)
C2	0.0439 (8)	0.0485 (10)	0.0488 (10)	0.0050 (7)	0.0058 (7)	−0.0025 (8)
C20	0.0483 (10)	0.0993 (18)	0.1017 (17)	−0.0118 (10)	0.0030 (10)	−0.0090 (14)
C10	0.0798 (13)	0.0608 (14)	0.0931 (16)	−0.0161 (10)	0.0202 (12)	−0.0003 (11)
C6	0.0569 (10)	0.0692 (13)	0.0477 (10)	−0.0006 (9)	0.0067 (8)	−0.0018 (9)
C14	0.0684 (13)	0.0708 (15)	0.1093 (19)	0.0035 (11)	−0.0308 (13)	−0.0254 (13)
C19	0.0511 (9)	0.0468 (10)	0.0441 (10)	−0.0031 (7)	−0.0004 (7)	−0.0015 (7)
C13	0.0499 (10)	0.0543 (13)	0.119 (2)	−0.0044 (9)	−0.0018 (11)	−0.0084 (12)
C12	0.0512 (9)	0.0415 (11)	0.0810 (14)	0.0022 (7)	0.0016 (9)	−0.0019 (9)
C15	0.0744 (13)	0.0752 (16)	0.0804 (14)	0.0126 (11)	−0.0187 (11)	−0.0219 (12)
C11	0.0803 (14)	0.0885 (18)	0.119 (2)	−0.0205 (12)	0.0373 (13)	0.0061 (15)

O1—C2	1.3605 (19)	C16—H16	0.93
O1—C1	1.409 (2)	C4—C5	1.374 (3)
O3—C9	1.339 (2)	C4—C3	1.378 (3)
O3—C10	1.440 (2)	C4—H4	0.93
O2—C9	1.205 (2)	C3—C2	1.391 (2)
O6—C19	1.3370 (19)	C3—H3	0.93
O6—C20	1.443 (2)	C5—C6	1.388 (3)
O4—C12	1.367 (2)	C5—H5	0.93
O4—C11	1.436 (2)	C1—H1A	0.96
N3—C18	1.280 (2)	C1—H1B	0.96
N3—N4	1.3742 (17)	C1—H1C	0.96
O5—C19	1.1922 (19)	C20—H20A	0.96
N1—C8	1.281 (2)	C20—H20B	0.96
N1—N2	1.3846 (19)	C20—H20C	0.96
N2—C9	1.348 (2)	C10—H10A	0.96
N2—H2N	0.86	C10—H10B	0.96
N4—C19	1.353 (2)	C10—H10C	0.96
N4—H4N	0.86	C6—H6	0.93
C7—C6	1.395 (2)	C14—C15	1.371 (3)
C7—C2	1.406 (2)	C14—C13	1.374 (3)
C7—C8	1.466 (2)	C14—H14	0.93
C17—C16	1.386 (3)	C13—C12	1.396 (3)
C17—C12	1.403 (2)	C13—H13	0.93
C17—C18	1.471 (2)	C15—H15	0.93
C18—H18	0.93	C11—H11A	0.96
C8—H8	0.93	C11—H11B	0.96
C16—C15	1.379 (3)	C11—H11C	0.96

C2—O1—C1	118.57 (14)	O1—C1—H1C	109.5
C9—O3—C10	116.02 (15)	H1A—C1—H1C	109.5
C19—O6—C20	117.40 (15)	H1B—C1—H1C	109.5
C12—O4—C11	117.97 (16)	O1—C2—C3	123.94 (16)
C18—N3—N4	115.85 (13)	O1—C2—C7	115.33 (14)
C8—N1—N2	114.99 (13)	C3—C2—C7	120.73 (15)
C9—N2—N1	119.64 (13)	O6—C20—H20A	109.5
C9—N2—H2N	120.2	O6—C20—H20B	109.5
N1—N2—H2N	120.2	H20A—C20—H20B	109.5
C19—N4—N3	118.82 (13)	O6—C20—H20C	109.5
C19—N4—H4N	120.6	H20A—C20—H20C	109.5
N3—N4—H4N	120.6	H20B—C20—H20C	109.5
C6—C7—C2	117.76 (16)	O3—C10—H10A	109.5
C6—C7—C8	123.29 (16)	O3—C10—H10B	109.5
C2—C7—C8	118.96 (14)	H10A—C10—H10B	109.5
C16—C17—C12	118.26 (16)	O3—C10—H10C	109.5
C16—C17—C18	120.86 (16)	H10A—C10—H10C	109.5
C12—C17—C18	120.84 (16)	H10B—C10—H10C	109.5
N3—C18—C17	119.80 (15)	C5—C6—C7	121.06 (17)
N3—C18—H18	120.1	C5—C6—H6	119.5
C17—C18—H18	120.1	C7—C6—H6	119.5
N1—C8—C7	122.99 (15)	C15—C14—C13	120.82 (19)
N1—C8—H8	118.5	C15—C14—H14	119.6
C7—C8—H8	118.5	C13—C14—H14	119.6
O2—C9—O3	124.73 (16)	O5—C19—O6	124.49 (15)
O2—C9—N2	125.42 (16)	O5—C19—N4	126.70 (14)
O3—C9—N2	109.84 (14)	O6—C19—N4	108.79 (14)
C15—C16—C17	121.7 (2)	C14—C13—C12	120.1 (2)
C15—C16—H16	119.2	C14—C13—H13	120.0
C17—C16—H16	119.2	C12—C13—H13	120.0
C5—C4—C3	120.38 (18)	O4—C12—C13	124.25 (18)
C5—C4—H4	119.8	O4—C12—C17	116.00 (15)
C3—C4—H4	119.8	C13—C12—C17	119.75 (19)
C4—C3—C2	119.93 (17)	C14—C15—C16	119.4 (2)
C4—C3—H3	120.0	C14—C15—H15	120.3
C2—C3—H3	120.0	C16—C15—H15	120.3
C4—C5—C6	120.14 (17)	O4—C11—H11A	109.5
C4—C5—H5	119.9	O4—C11—H11B	109.5
C6—C5—H5	119.9	H11A—C11—H11B	109.5
O1—C1—H1A	109.5	O4—C11—H11C	109.5
O1—C1—H1B	109.5	H11A—C11—H11C	109.5
H1A—C1—H1B	109.5	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5	0.86	2.08	2.938 (2)	173
N4—H4N···N1ⁱ	0.86	2.42	3.279 (2)	177
C1—H1A···O2ⁱ	0.96	2.52	3.472 (2)	170
C11—H11B···Cg1ⁱⁱ	0.96	2.87	3.826 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O5	0.86	2.08	2.938 (2)	173
N4—H4N⋯N1ⁱ	0.86	2.42	3.279 (2)	177
C1—H1A⋯O2ⁱ	0.96	2.52	3.472 (2)	170
C11—H11B⋯Cg1ⁱⁱ	0.96	2.87	3.826 (3)	175

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Design, synthesis, and evaluation of Phe-Gly mimetics: heterocyclic building blocks for pseudopeptides.

Authors: S Borg; R C Vollinga; M Labarre; K Payza; L Terenius; K Luthman
Journal: J Med Chem Date: 1999-10-21 Impact factor: 7.446

2 in total