Literature DB >> 21578451

N'-(5-Hydr-oxy-2-nitro-benzyl-idene)-2-methoxy-benzohydrazide.

De-Suo Yang1.   

Abstract

The asymmetric unit of the title compound, C(15)H(13)N(3)O(5), contains two independent mol-ecules. Each mol-ecule displays an E configuration with respect to its C=N double bond. The dihedral angles between the two benzene rings are 11.1 (2) and 10.9 (2)° in the two mol-ecules. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming chains running along the a axis.

Entities:  

Year:  2009        PMID: 21578451      PMCID: PMC2971021          DOI: 10.1107/S1600536809043840

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


Related literature

For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009 ▶); Charkoudian et al. (2007 ▶); Cukurovali et al. (2006 ▶). For related structures, see: Yang (2008a ▶,b ▶,c ▶,d ▶,e, 2007a ▶,b ▶,c ▶); Yang & Guo (2006 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13N3O5 M = 315.28 Triclinic, a = 8.7540 (9) Å b = 9.0529 (9) Å c = 18.2159 (17) Å α = 86.902 (5)° β = 83.023 (5)° γ = 82.509 (5)° V = 1419.6 (2) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 298 K 0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.983 8779 measured reflections 6066 independent reflections 4236 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.123 S = 1.04 6066 reflections 425 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.26 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 global, I. DOI: 10.1107/S1600536809043840/wn2358sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043840/wn2358Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H13N3O5Z = 4
Mr = 315.28F(000) = 656
Triclinic, P1Dx = 1.475 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7540 (9) ÅCell parameters from 2340 reflections
b = 9.0529 (9) Åθ = 2.5–25.3°
c = 18.2159 (17) ŵ = 0.11 mm1
α = 86.902 (5)°T = 298 K
β = 83.023 (5)°Block, colorless
γ = 82.509 (5)°0.17 × 0.15 × 0.15 mm
V = 1419.6 (2) Å3
Bruker SMART CCD diffractometer6066 independent reflections
Radiation source: fine-focus sealed tube4236 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→11
Tmin = 0.981, Tmax = 0.983k = −11→9
8779 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1933P] where P = (Fo2 + 2Fc2)/3
6066 reflections(Δ/σ)max = 0.001
425 parametersΔρmax = 0.23 e Å3
2 restraintsΔρmin = −0.26 e Å3
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.
xyzUiso*/Ueq
O10.43038 (17)0.56766 (15)0.20225 (9)0.0651 (4)
O20.51734 (15)0.97729 (14)0.11083 (7)0.0496 (3)
O30.04575 (17)0.86066 (17)−0.04665 (8)0.0648 (4)
O4−0.19271 (18)0.88756 (16)−0.06698 (8)0.0642 (4)
O5−0.22760 (16)0.36644 (15)0.16573 (7)0.0516 (4)
H5−0.17930.36390.20170.077*
O60.93551 (17)0.39747 (18)0.28075 (8)0.0630 (4)
O71.02232 (16)0.21547 (16)0.48449 (7)0.0548 (4)
O80.54241 (17)−0.09248 (17)0.43071 (8)0.0655 (4)
O90.30249 (18)−0.12659 (17)0.44316 (8)0.0662 (4)
O100.27735 (16)0.33708 (14)0.18156 (7)0.0489 (3)
H100.32490.40940.18140.073*
N10.20958 (17)0.68586 (16)0.12448 (8)0.0415 (4)
N20.32509 (17)0.76663 (16)0.13956 (9)0.0426 (4)
N3−0.08536 (19)0.82546 (17)−0.03512 (8)0.0426 (4)
N40.71155 (17)0.24869 (17)0.34137 (8)0.0405 (4)
N50.82807 (18)0.27753 (18)0.38088 (8)0.0437 (4)
N60.41209 (19)−0.06591 (17)0.41211 (8)0.0435 (4)
C1−0.02579 (19)0.67167 (19)0.07731 (9)0.0346 (4)
C2−0.1160 (2)0.70609 (19)0.01894 (9)0.0357 (4)
C3−0.2360 (2)0.6249 (2)0.00901 (10)0.0413 (4)
H3−0.29260.6485−0.03100.050*
C4−0.2708 (2)0.5109 (2)0.05763 (10)0.0433 (4)
H4−0.35050.45640.05070.052*
C5−0.1862 (2)0.47659 (19)0.11782 (9)0.0378 (4)
C6−0.06376 (19)0.55545 (19)0.12606 (9)0.0366 (4)
H6−0.00570.52960.16530.044*
C70.1012 (2)0.7541 (2)0.09190 (10)0.0398 (4)
H70.10110.85420.07730.048*
C80.4347 (2)0.6969 (2)0.17976 (10)0.0404 (4)
C90.56063 (19)0.7798 (2)0.19878 (10)0.0380 (4)
C100.6016 (2)0.9147 (2)0.16516 (10)0.0395 (4)
C110.7241 (2)0.9775 (2)0.18779 (11)0.0497 (5)
H110.75101.06730.16610.060*
C120.8050 (2)0.9064 (3)0.24229 (12)0.0584 (6)
H120.88650.94920.25730.070*
C130.7685 (2)0.7741 (3)0.27496 (12)0.0576 (6)
H130.82500.72670.31150.069*
C140.6473 (2)0.7120 (2)0.25317 (10)0.0479 (5)
H140.62240.62200.27540.058*
C150.5651 (2)1.1071 (2)0.07190 (12)0.0562 (5)
H15A0.55491.18700.10540.084*
H15B0.50111.13530.03300.084*
H15C0.67141.08660.05110.084*
C160.47579 (19)0.15649 (19)0.33463 (9)0.0350 (4)
C170.3836 (2)0.04192 (19)0.35190 (9)0.0352 (4)
C180.2637 (2)0.0237 (2)0.31102 (10)0.0404 (4)
H180.2052−0.05470.32310.048*
C190.2313 (2)0.1207 (2)0.25315 (10)0.0419 (4)
H190.15250.10710.22510.050*
C200.3170 (2)0.23981 (19)0.23648 (9)0.0373 (4)
C210.43944 (19)0.25484 (19)0.27658 (9)0.0365 (4)
H210.49830.33290.26410.044*
C220.6037 (2)0.1839 (2)0.37580 (10)0.0400 (4)
H220.60480.15440.42550.048*
C230.9387 (2)0.3552 (2)0.34549 (10)0.0413 (4)
C241.0637 (2)0.3942 (2)0.38721 (10)0.0420 (4)
C251.1028 (2)0.3282 (2)0.45480 (11)0.0451 (5)
C261.2213 (2)0.3780 (3)0.48783 (13)0.0611 (6)
H261.24810.33510.53280.073*
C271.2983 (3)0.4902 (3)0.45383 (16)0.0701 (7)
H271.37510.52460.47700.084*
C281.2647 (3)0.5530 (3)0.38670 (15)0.0669 (7)
H281.31990.62720.36370.080*
C291.1482 (2)0.5044 (2)0.35392 (12)0.0531 (5)
H291.12520.54640.30820.064*
C301.0611 (3)0.1437 (3)0.55204 (11)0.0626 (6)
H30A1.16980.10730.54720.094*
H30B1.00190.06170.56370.094*
H30C1.03800.21340.59090.094*
H20.331 (3)0.8598 (14)0.1214 (12)0.080*
H5A0.833 (3)0.243 (2)0.4276 (7)0.080*
U11U22U33U12U13U23
O10.0588 (9)0.0480 (9)0.0964 (12)−0.0217 (7)−0.0397 (8)0.0299 (8)
O20.0452 (8)0.0470 (8)0.0607 (9)−0.0190 (6)−0.0160 (6)0.0159 (6)
O30.0507 (9)0.0761 (11)0.0666 (10)−0.0205 (8)−0.0020 (7)0.0268 (8)
O40.0730 (10)0.0556 (9)0.0715 (10)−0.0181 (7)−0.0394 (8)0.0242 (7)
O50.0604 (9)0.0534 (8)0.0477 (8)−0.0284 (7)−0.0168 (7)0.0145 (6)
O60.0574 (9)0.0893 (11)0.0492 (9)−0.0331 (8)−0.0201 (7)0.0254 (8)
O70.0522 (8)0.0695 (10)0.0476 (8)−0.0127 (7)−0.0238 (7)0.0083 (7)
O80.0525 (9)0.0743 (10)0.0677 (10)−0.0008 (7)−0.0205 (8)0.0273 (8)
O90.0741 (11)0.0728 (10)0.0595 (9)−0.0395 (8)−0.0200 (8)0.0271 (8)
O100.0550 (9)0.0468 (8)0.0502 (8)−0.0150 (6)−0.0250 (6)0.0149 (6)
N10.0358 (8)0.0410 (9)0.0513 (9)−0.0146 (7)−0.0137 (7)0.0082 (7)
N20.0386 (8)0.0378 (8)0.0558 (10)−0.0144 (7)−0.0182 (7)0.0112 (7)
N30.0461 (9)0.0428 (9)0.0404 (9)−0.0097 (7)−0.0102 (7)0.0051 (7)
N40.0372 (8)0.0488 (9)0.0391 (8)−0.0115 (7)−0.0156 (7)0.0050 (7)
N50.0394 (9)0.0598 (10)0.0360 (8)−0.0171 (7)−0.0143 (7)0.0085 (7)
N60.0506 (10)0.0404 (9)0.0406 (9)−0.0082 (7)−0.0098 (7)0.0053 (7)
C10.0298 (9)0.0360 (9)0.0385 (9)−0.0057 (7)−0.0052 (7)0.0017 (7)
C20.0378 (9)0.0355 (9)0.0339 (9)−0.0055 (7)−0.0052 (7)0.0022 (7)
C30.0422 (10)0.0476 (11)0.0368 (10)−0.0089 (8)−0.0142 (8)0.0024 (8)
C40.0435 (11)0.0459 (11)0.0450 (11)−0.0171 (8)−0.0119 (8)0.0011 (8)
C50.0410 (10)0.0360 (9)0.0365 (9)−0.0083 (8)−0.0029 (8)0.0022 (7)
C60.0337 (9)0.0405 (10)0.0371 (9)−0.0076 (7)−0.0097 (7)0.0043 (7)
C70.0388 (10)0.0363 (10)0.0458 (10)−0.0105 (8)−0.0100 (8)0.0091 (8)
C80.0368 (10)0.0391 (10)0.0471 (11)−0.0101 (8)−0.0108 (8)0.0078 (8)
C90.0314 (9)0.0426 (10)0.0409 (10)−0.0061 (7)−0.0060 (7)−0.0028 (8)
C100.0325 (9)0.0446 (10)0.0422 (10)−0.0068 (8)−0.0044 (8)−0.0033 (8)
C110.0421 (11)0.0505 (12)0.0602 (13)−0.0177 (9)−0.0063 (9)−0.0070 (10)
C120.0470 (12)0.0711 (15)0.0638 (14)−0.0138 (11)−0.0193 (10)−0.0179 (12)
C130.0543 (13)0.0689 (15)0.0540 (13)−0.0043 (11)−0.0241 (10)−0.0102 (11)
C140.0476 (11)0.0512 (12)0.0459 (11)−0.0042 (9)−0.0124 (9)0.0013 (9)
C150.0533 (13)0.0510 (12)0.0652 (14)−0.0200 (10)−0.0035 (10)0.0141 (10)
C160.0319 (9)0.0398 (10)0.0327 (9)−0.0039 (7)−0.0040 (7)0.0022 (7)
C170.0369 (9)0.0353 (9)0.0331 (9)−0.0036 (7)−0.0058 (7)0.0025 (7)
C180.0431 (10)0.0391 (10)0.0417 (10)−0.0153 (8)−0.0075 (8)0.0032 (8)
C190.0421 (10)0.0451 (11)0.0421 (10)−0.0109 (8)−0.0149 (8)0.0007 (8)
C200.0386 (10)0.0392 (10)0.0341 (9)−0.0034 (8)−0.0080 (7)0.0040 (7)
C210.0350 (9)0.0379 (10)0.0383 (9)−0.0094 (7)−0.0081 (7)0.0050 (7)
C220.0385 (10)0.0479 (11)0.0351 (9)−0.0090 (8)−0.0116 (8)0.0084 (8)
C230.0371 (10)0.0455 (11)0.0426 (10)−0.0073 (8)−0.0096 (8)0.0045 (8)
C240.0312 (9)0.0459 (11)0.0498 (11)−0.0020 (8)−0.0087 (8)−0.0084 (9)
C250.0348 (10)0.0507 (11)0.0509 (12)−0.0012 (9)−0.0104 (8)−0.0107 (9)
C260.0478 (12)0.0715 (15)0.0688 (15)−0.0012 (11)−0.0264 (11)−0.0182 (12)
C270.0467 (13)0.0724 (16)0.099 (2)−0.0132 (12)−0.0231 (13)−0.0300 (15)
C280.0499 (13)0.0615 (15)0.0938 (19)−0.0185 (11)−0.0072 (13)−0.0183 (13)
C290.0434 (11)0.0504 (12)0.0667 (14)−0.0097 (9)−0.0041 (10)−0.0077 (10)
C300.0601 (14)0.0785 (16)0.0502 (12)0.0022 (12)−0.0255 (10)0.0047 (11)
O1—C81.223 (2)C9—C101.405 (3)
O2—C101.361 (2)C10—C111.391 (2)
O2—C151.423 (2)C11—C121.373 (3)
O3—N31.2217 (19)C11—H110.9300
O4—N31.2228 (19)C12—C131.367 (3)
O5—C51.346 (2)C12—H120.9300
O5—H50.8200C13—C141.371 (3)
O6—C231.223 (2)C13—H130.9300
O7—C251.366 (2)C14—H140.9300
O7—C301.418 (2)C15—H15A0.9600
O8—N61.220 (2)C15—H15B0.9600
O9—N61.231 (2)C15—H15C0.9600
O10—C201.344 (2)C16—C211.385 (2)
O10—H100.8200C16—C171.395 (2)
N1—C71.256 (2)C16—C221.475 (2)
N1—N21.3837 (19)C17—C181.390 (2)
N2—C81.348 (2)C18—C191.367 (2)
N2—H20.895 (10)C18—H180.9300
N3—C21.451 (2)C19—C201.393 (2)
N4—C221.260 (2)C19—H190.9300
N4—N51.3764 (19)C20—C211.393 (2)
N5—C231.351 (2)C21—H210.9300
N5—H5A0.895 (10)C22—H220.9300
N6—C171.451 (2)C23—C241.493 (2)
C1—C61.387 (2)C24—C291.388 (3)
C1—C21.399 (2)C24—C251.400 (3)
C1—C71.474 (2)C25—C261.394 (3)
C2—C31.392 (2)C26—C271.371 (3)
C3—C41.364 (2)C26—H260.9300
C3—H30.9300C27—C281.368 (3)
C4—C51.396 (2)C27—H270.9300
C4—H40.9300C28—C291.373 (3)
C5—C61.390 (2)C28—H280.9300
C6—H60.9300C29—H290.9300
C7—H70.9300C30—H30A0.9600
C8—C91.495 (2)C30—H30B0.9600
C9—C141.389 (3)C30—H30C0.9600
C10—O2—C15117.91 (15)C13—C14—C9121.9 (2)
C5—O5—H5109.5C13—C14—H14119.1
C25—O7—C30118.82 (15)C9—C14—H14119.1
C20—O10—H10109.5O2—C15—H15A109.5
C7—N1—N2117.33 (15)O2—C15—H15B109.5
C8—N2—N1117.45 (14)H15A—C15—H15B109.5
C8—N2—H2120.6 (15)O2—C15—H15C109.5
N1—N2—H2121.8 (15)H15A—C15—H15C109.5
O3—N3—O4122.64 (16)H15B—C15—H15C109.5
O3—N3—C2118.98 (15)C21—C16—C17117.22 (15)
O4—N3—C2118.38 (15)C21—C16—C22118.02 (16)
C22—N4—N5117.22 (15)C17—C16—C22124.70 (15)
C23—N5—N4117.46 (15)C18—C17—C16121.56 (15)
C23—N5—H5A121.0 (15)C18—C17—N6117.20 (15)
N4—N5—H5A121.5 (16)C16—C17—N6121.22 (15)
O8—N6—O9122.25 (16)C19—C18—C17120.27 (16)
O8—N6—C17119.37 (16)C19—C18—H18119.9
O9—N6—C17118.38 (15)C17—C18—H18119.9
C6—C1—C2117.02 (15)C18—C19—C20119.51 (16)
C6—C1—C7118.44 (15)C18—C19—H19120.2
C2—C1—C7124.49 (15)C20—C19—H19120.2
C3—C2—C1121.54 (16)O10—C20—C21122.29 (16)
C3—C2—N3117.21 (15)O10—C20—C19118.01 (15)
C1—C2—N3121.23 (15)C21—C20—C19119.70 (16)
C4—C3—C2120.29 (16)C16—C21—C20121.65 (16)
C4—C3—H3119.9C16—C21—H21119.2
C2—C3—H3119.9C20—C21—H21119.2
C3—C4—C5119.66 (16)N4—C22—C16117.72 (16)
C3—C4—H4120.2N4—C22—H22121.1
C5—C4—H4120.2C16—C22—H22121.1
O5—C5—C6122.68 (16)O6—C23—N5121.09 (16)
O5—C5—C4117.72 (16)O6—C23—C24119.70 (17)
C6—C5—C4119.59 (16)N5—C23—C24119.17 (16)
C1—C6—C5121.84 (16)C29—C24—C25118.61 (17)
C1—C6—H6119.1C29—C24—C23115.53 (17)
C5—C6—H6119.1C25—C24—C23125.85 (18)
N1—C7—C1118.35 (16)O7—C25—C26123.40 (19)
N1—C7—H7120.8O7—C25—C24117.22 (16)
C1—C7—H7120.8C26—C25—C24119.4 (2)
O1—C8—N2120.76 (16)C27—C26—C25119.8 (2)
O1—C8—C9119.55 (16)C27—C26—H26120.1
N2—C8—C9119.67 (15)C25—C26—H26120.1
C14—C9—C10118.09 (16)C28—C27—C26121.6 (2)
C14—C9—C8115.65 (16)C28—C27—H27119.2
C10—C9—C8126.22 (16)C26—C27—H27119.2
O2—C10—C11123.15 (17)C27—C28—C29118.8 (2)
O2—C10—C9117.06 (15)C27—C28—H28120.6
C11—C10—C9119.79 (17)C29—C28—H28120.6
C12—C11—C10119.68 (19)C28—C29—C24121.7 (2)
C12—C11—H11120.2C28—C29—H29119.1
C10—C11—H11120.2C24—C29—H29119.1
C13—C12—C11121.47 (19)O7—C30—H30A109.5
C13—C12—H12119.3O7—C30—H30B109.5
C11—C12—H12119.3H30A—C30—H30B109.5
C12—C13—C14119.1 (2)O7—C30—H30C109.5
C12—C13—H13120.5H30A—C30—H30C109.5
C14—C13—H13120.5H30B—C30—H30C109.5
D—H···AD—HH···AD···AD—H···A
O5—H5···O6i0.821.912.721 (2)169
O10—H10···O10.821.882.689 (2)168
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O5—H5⋯O6i0.821.912.721 (2)169
O10—H10⋯O10.821.882.689 (2)168

Symmetry code: (i) .

  8 in total

1.  Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring.

Authors:  Alaaddin Cukurovali; Ibrahim Yilmaz; Seher Gur; Cavit Kazaz
Journal:  Eur J Med Chem       Date:  2005-12-27       Impact factor: 6.514

2.  A short history of SHELX.

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

3.  Modifications of boronic ester pro-chelators triggered by hydrogen peroxide tune reactivity to inhibit metal-promoted oxidative stress.

Authors:  Louise K Charkoudian; David M Pham; Ashley M Kwon; Abbey D Vangeloff; Katherine J Franz
Journal:  Dalton Trans       Date:  2007-09-19       Impact factor: 4.390

4.  (E)-4-Chloro-N'-(4-hydroxy-benzyl-idene)-benzohydrazide.

Authors:  De-Suo Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-30

5.  (E)-4-Chloro-N'-[1-(4-hydroxy-phenyl)-ethylidene]benzohydrazide.

Authors:  De-Suo Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-30

6.  4-Chloro-N'-(2-hydr-oxy-1-naphthyl-idene)benzohydrazide.

Authors:  De-Suo Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-16

7.  Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone.

Authors:  Prakash Gouda Avaji; C H Vinod Kumar; Sangamesh A Patil; K N Shivananda; C Nagaraju
Journal:  Eur J Med Chem       Date:  2009-04-05       Impact factor: 6.514

8.  4-Chloro-N'-(5-chloro-2-hydroxy-benzyl-idene)benzohydrazide.

Authors:  De-Suo Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-16
  8 in total
  1 in total

1.  (E)-4-Amino-N'-(5-chloro-2-hy-droxy-benzyl-idene)benzohydrazide.

Authors:  Zhong-Feng Shi; Jia-Ming Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-28
  1 in total

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