Literature DB >> 23476257

5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phen-yl]-4,5-dihydro-furan-3-carbonitrile.

V Rajni Swamy1, R V Krishnakumar, N Srinivasan, P Gunasekaran, S Perumal.   

Abstract

In the title compound, C29H24N2O2, the hydrofuran ring is twisted with puckering parameters Q = 0.1553 (16) Å and ϕ = 305.0 (6)°. In the crystal, the graph-set motifs of the inter-action pattern are an R2(2)(16) motif involving dimers through N-H⋯N hydrogen bonds across centres of inversion and a C(6) motif through C-H⋯O hydrogen-bond between glide-related mol-ecules. Together, these generate [101] ladder-like chains.

Entities:  

Year:  2012        PMID: 23476257      PMCID: PMC3589021          DOI: 10.1107/S1600536812046764

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


Related literature

For related structures, see: Suresh et al. (2012a ▶,b ▶,c ▶). For discussion on aromatic inter­actions, see: Bloom & Wheeler (2011 ▶); Martinez & Iverson (2012 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H24N2O2 M = 432.50 Monoclinic, a = 17.1073 (4) Å b = 8.1230 (2) Å c = 17.6160 (4) Å β = 110.325 (1)° V = 2295.55 (9) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 298 K 0.30 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.978, T max = 0.986 21711 measured reflections 4455 independent reflections 2979 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.115 S = 1.03 4455 reflections 313 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.14 e Å−3 Δρmin = −0.15 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046764/rz5022sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046764/rz5022Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812046764/rz5022Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C29H24N2O2F(000) = 912
Mr = 432.50Dx = 1.251 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4455 reflections
a = 17.1073 (4) Åθ = 2.5–25.9°
b = 8.1230 (2) ŵ = 0.08 mm1
c = 17.6160 (4) ÅT = 298 K
β = 110.325 (1)°Block, yellow
V = 2295.55 (9) Å30.30 × 0.24 × 0.18 mm
Z = 4
Bruker SMART APEXII CCD diffractometer4455 independent reflections
Radiation source: fine-focus sealed tube2979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and φ scansθmax = 25.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −21→20
Tmin = 0.978, Tmax = 0.986k = −9→9
21711 measured reflectionsl = −21→21
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3844P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4455 reflectionsΔρmax = 0.14 e Å3
313 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0037 (8)
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
O10.27185 (7)0.17860 (13)0.26234 (6)0.0553 (3)
O20.14529 (8)0.34499 (18)0.16547 (7)0.0792 (4)
N10.49191 (10)0.5602 (2)0.31131 (9)0.0752 (5)
N20.40406 (11)0.3263 (2)0.52408 (9)0.0694 (5)
H20.4434 (13)0.352 (3)0.5722 (13)0.088 (6)*
C380.41572 (11)0.3360 (2)0.45193 (10)0.0611 (5)
H380.46520.36690.44510.073*
C370.32392 (12)0.2788 (2)0.51144 (10)0.0623 (5)
C360.28453 (16)0.2536 (3)0.56731 (12)0.0808 (6)
H360.31240.26900.62240.097*
C350.20349 (17)0.2056 (3)0.53802 (15)0.0907 (7)
H350.17560.18620.57400.109*
C340.16088 (14)0.1847 (3)0.45517 (14)0.0828 (6)
H340.10510.15370.43710.099*
C330.20012 (12)0.2091 (2)0.39978 (12)0.0640 (5)
H330.1721 (10)0.194 (2)0.3426 (10)0.063 (5)*
C320.28362 (11)0.25594 (19)0.42818 (9)0.0527 (4)
C310.34395 (10)0.29363 (19)0.39077 (9)0.0510 (4)
C30.33352 (9)0.28117 (19)0.30620 (9)0.0481 (4)
C20.37493 (10)0.34966 (19)0.26182 (9)0.0486 (4)
C10.43942 (11)0.4654 (2)0.28977 (9)0.0544 (4)
C50.34552 (9)0.27757 (19)0.17735 (9)0.0477 (4)
H50.33020.36630.13710.057*
C40.26595 (9)0.18830 (19)0.17900 (8)0.0483 (4)
H40.26410.07690.15710.058*
C410.18682 (10)0.2796 (2)0.13117 (9)0.0505 (4)
C420.16376 (9)0.28783 (19)0.04210 (9)0.0472 (4)
C430.20139 (11)0.1912 (2)0.00015 (10)0.0613 (5)
H430.24400.11940.02810.074*
C440.17592 (13)0.2007 (3)−0.08313 (11)0.0751 (6)
H440.20120.1348−0.11110.090*
C450.11360 (13)0.3069 (2)−0.12478 (11)0.0725 (5)
H450.09660.3129−0.18090.087*
C460.07638 (12)0.4040 (3)−0.08392 (11)0.0741 (5)
H460.03430.4767−0.11210.089*
C470.10122 (11)0.3943 (2)−0.00096 (10)0.0633 (5)
H470.07550.46040.02650.076*
C510.41055 (9)0.16822 (19)0.16311 (9)0.0486 (4)
C520.44866 (12)0.2118 (2)0.10860 (11)0.0718 (5)
H520.43130.30590.07720.086*
C530.51201 (13)0.1176 (3)0.10024 (12)0.0803 (6)
H530.53650.14980.06300.096*
C540.54025 (11)−0.0221 (2)0.14503 (10)0.0631 (5)
C550.49997 (10)−0.0680 (2)0.19778 (10)0.0579 (4)
H550.5163−0.16400.22800.070*
C560.43633 (10)0.0251 (2)0.20650 (9)0.0518 (4)
H560.4086 (9)−0.0097 (19)0.2440 (9)0.059 (4)*
C60.61471 (13)−0.1150 (3)0.14021 (12)0.0827 (6)
H60.6245−0.07650.09160.099*
C70.69188 (13)−0.0692 (4)0.21299 (13)0.1129 (9)
H7A0.6812−0.09010.26210.169*
H7B0.70430.04530.21010.169*
H7C0.7385−0.13430.21230.169*
C80.60164 (18)−0.2977 (3)0.1318 (2)0.1309 (11)
H8A0.5946−0.34080.17970.196*
H8B0.6492−0.34840.12440.196*
H8C0.5528−0.32080.08570.196*
U11U22U33U12U13U23
O10.0631 (7)0.0602 (7)0.0400 (6)−0.0138 (6)0.0145 (5)−0.0035 (5)
O20.0800 (9)0.1019 (10)0.0621 (8)0.0212 (8)0.0331 (7)−0.0097 (7)
N10.0769 (11)0.0719 (11)0.0629 (10)−0.0211 (9)0.0067 (8)−0.0012 (8)
N20.0827 (12)0.0747 (11)0.0406 (9)−0.0067 (9)0.0087 (8)−0.0032 (7)
C380.0699 (11)0.0623 (11)0.0458 (10)−0.0031 (9)0.0134 (8)−0.0008 (8)
C370.0830 (14)0.0546 (10)0.0484 (10)0.0046 (10)0.0217 (9)0.0016 (8)
C360.1129 (18)0.0812 (14)0.0558 (12)0.0064 (13)0.0389 (12)0.0030 (10)
C350.1152 (19)0.0943 (17)0.0842 (16)0.0108 (15)0.0619 (15)0.0097 (13)
C340.0788 (14)0.0842 (15)0.0955 (17)0.0055 (12)0.0432 (13)0.0062 (12)
C330.0687 (12)0.0613 (11)0.0629 (12)0.0076 (9)0.0242 (10)0.0011 (9)
C320.0651 (11)0.0443 (9)0.0472 (9)0.0069 (8)0.0176 (8)0.0011 (7)
C310.0603 (10)0.0470 (9)0.0413 (9)0.0028 (8)0.0120 (7)0.0004 (7)
C30.0512 (9)0.0442 (9)0.0435 (9)0.0018 (7)0.0094 (7)−0.0024 (7)
C20.0511 (9)0.0465 (9)0.0438 (8)−0.0020 (8)0.0107 (7)−0.0027 (7)
C10.0584 (10)0.0531 (10)0.0450 (9)−0.0036 (9)0.0095 (8)−0.0004 (8)
C50.0520 (9)0.0473 (9)0.0402 (8)−0.0047 (7)0.0115 (7)0.0002 (7)
C40.0556 (9)0.0490 (9)0.0394 (8)−0.0055 (7)0.0155 (7)−0.0059 (7)
C410.0511 (9)0.0531 (9)0.0485 (9)−0.0050 (8)0.0188 (8)−0.0101 (7)
C420.0453 (9)0.0486 (9)0.0460 (9)−0.0057 (7)0.0137 (7)−0.0074 (7)
C430.0677 (11)0.0652 (11)0.0506 (10)0.0086 (9)0.0199 (8)−0.0026 (8)
C440.0912 (14)0.0846 (14)0.0548 (11)0.0057 (12)0.0320 (11)−0.0082 (10)
C450.0856 (14)0.0795 (14)0.0462 (10)−0.0104 (11)0.0149 (10)0.0021 (10)
C460.0728 (12)0.0755 (13)0.0581 (12)0.0063 (10)0.0030 (10)0.0016 (10)
C470.0568 (10)0.0696 (12)0.0568 (11)0.0039 (9)0.0110 (8)−0.0088 (9)
C510.0525 (9)0.0532 (9)0.0392 (8)−0.0068 (8)0.0148 (7)−0.0013 (7)
C520.0848 (13)0.0751 (13)0.0671 (12)0.0079 (11)0.0410 (11)0.0220 (10)
C530.0857 (14)0.1008 (16)0.0742 (13)0.0119 (12)0.0528 (11)0.0227 (12)
C540.0628 (11)0.0780 (13)0.0539 (10)0.0029 (10)0.0271 (9)−0.0005 (9)
C550.0620 (11)0.0598 (11)0.0529 (10)0.0034 (9)0.0212 (8)0.0046 (8)
C560.0579 (10)0.0575 (10)0.0445 (9)−0.0049 (8)0.0234 (8)0.0026 (8)
C60.0760 (13)0.1117 (18)0.0713 (13)0.0184 (13)0.0393 (11)0.0067 (12)
C70.0725 (15)0.190 (3)0.0792 (16)0.0226 (16)0.0300 (13)0.0053 (16)
C80.125 (2)0.110 (2)0.182 (3)0.0356 (18)0.084 (2)−0.005 (2)
O1—C31.3557 (18)C42—C431.381 (2)
O1—C41.4384 (17)C43—C441.380 (2)
O2—C411.2043 (18)C43—H430.9300
N1—C11.143 (2)C44—C451.370 (3)
N2—C381.356 (2)C44—H440.9300
N2—C371.366 (2)C45—C461.365 (3)
N2—H20.91 (2)C45—H450.9300
C38—C311.367 (2)C46—C471.375 (2)
C38—H380.9300C46—H460.9300
C37—C361.388 (3)C47—H470.9300
C37—C321.399 (2)C51—C561.377 (2)
C36—C351.358 (3)C51—C521.381 (2)
C36—H360.9300C52—C531.376 (3)
C35—C341.397 (3)C52—H520.9300
C35—H350.9300C53—C541.371 (3)
C34—C331.378 (3)C53—H530.9300
C34—H340.9300C54—C551.387 (2)
C33—C321.392 (2)C54—C61.508 (3)
C33—H330.961 (16)C55—C561.377 (2)
C32—C311.437 (2)C55—H550.9300
C31—C31.441 (2)C56—H560.978 (15)
C3—C21.344 (2)C6—C81.501 (3)
C2—C11.402 (2)C6—C71.533 (3)
C2—C51.513 (2)C6—H60.9800
C5—C511.511 (2)C7—H7A0.9600
C5—C41.552 (2)C7—H7B0.9600
C5—H50.9800C7—H7C0.9600
C4—C411.516 (2)C8—H8A0.9600
C4—H40.9800C8—H8B0.9600
C41—C421.480 (2)C8—H8C0.9600
C42—C471.380 (2)
C3—O1—C4108.23 (11)C43—C42—C41122.63 (15)
C38—N2—C37109.26 (16)C44—C43—C42120.21 (17)
C38—N2—H2124.0 (13)C44—C43—H43119.9
C37—N2—H2126.6 (12)C42—C43—H43119.9
N2—C38—C31109.88 (16)C45—C44—C43120.31 (17)
N2—C38—H38125.1C45—C44—H44119.8
C31—C38—H38125.1C43—C44—H44119.8
N2—C37—C36129.28 (18)C46—C45—C44120.01 (17)
N2—C37—C32108.03 (15)C46—C45—H45120.0
C36—C37—C32122.68 (19)C44—C45—H45120.0
C35—C36—C37117.1 (2)C45—C46—C47119.89 (18)
C35—C36—H36121.4C45—C46—H46120.1
C37—C36—H36121.4C47—C46—H46120.1
C36—C35—C34121.69 (19)C46—C47—C42120.99 (17)
C36—C35—H35119.2C46—C47—H47119.5
C34—C35—H35119.2C42—C47—H47119.5
C33—C34—C35121.1 (2)C56—C51—C52117.70 (15)
C33—C34—H34119.4C56—C51—C5121.09 (13)
C35—C34—H34119.4C52—C51—C5121.15 (15)
C34—C33—C32118.44 (19)C53—C52—C51120.76 (17)
C34—C33—H33122.3 (10)C53—C52—H52119.6
C32—C33—H33119.2 (10)C51—C52—H52119.6
C33—C32—C37118.90 (16)C54—C53—C52122.15 (16)
C33—C32—C31134.73 (15)C54—C53—H53118.9
C37—C32—C31106.34 (15)C52—C53—H53118.9
C38—C31—C32106.48 (14)C53—C54—C55116.79 (16)
C38—C31—C3125.98 (15)C53—C54—C6121.17 (16)
C32—C31—C3127.46 (15)C55—C54—C6121.95 (17)
C2—C3—O1112.70 (13)C56—C55—C54121.53 (17)
C2—C3—C31132.15 (15)C56—C55—H55119.2
O1—C3—C31115.13 (13)C54—C55—H55119.2
C3—C2—C1125.62 (14)C51—C56—C55121.00 (15)
C3—C2—C5110.44 (13)C51—C56—H56118.8 (9)
C1—C2—C5123.86 (14)C55—C56—H56120.2 (9)
N1—C1—C2178.90 (18)C8—C6—C54113.64 (18)
C51—C5—C2112.23 (12)C8—C6—C7112.2 (2)
C51—C5—C4115.45 (13)C54—C6—C7109.29 (17)
C2—C5—C499.01 (11)C8—C6—H6107.1
C51—C5—H5109.9C54—C6—H6107.1
C2—C5—H5109.9C7—C6—H6107.1
C4—C5—H5109.9C6—C7—H7A109.5
O1—C4—C41109.06 (12)C6—C7—H7B109.5
O1—C4—C5107.08 (11)H7A—C7—H7B109.5
C41—C4—C5112.38 (12)C6—C7—H7C109.5
O1—C4—H4109.4H7A—C7—H7C109.5
C41—C4—H4109.4H7B—C7—H7C109.5
C5—C4—H4109.4C6—C8—H8A109.5
O2—C41—C42121.68 (15)C6—C8—H8B109.5
O2—C41—C4120.35 (14)H8A—C8—H8B109.5
C42—C41—C4117.96 (13)C6—C8—H8C109.5
C47—C42—C43118.59 (15)H8A—C8—H8C109.5
C47—C42—C41118.78 (14)H8B—C8—H8C109.5
C37—N2—C38—C31−0.6 (2)C2—C5—C4—O1−15.46 (14)
C38—N2—C37—C36−179.78 (19)C51—C5—C4—C41−135.75 (13)
C38—N2—C37—C320.6 (2)C2—C5—C4—C41104.28 (13)
N2—C37—C36—C35−179.8 (2)O1—C4—C41—O27.6 (2)
C32—C37—C36—C35−0.3 (3)C5—C4—C41—O2−110.94 (17)
C37—C36—C35—C34−1.0 (3)O1—C4—C41—C42−173.49 (12)
C36—C35—C34—C331.3 (3)C5—C4—C41—C4267.93 (17)
C35—C34—C33—C32−0.2 (3)O2—C41—C42—C4710.5 (2)
C34—C33—C32—C37−1.0 (3)C4—C41—C42—C47−168.32 (14)
C34—C33—C32—C31−179.20 (18)O2—C41—C42—C43−168.36 (17)
N2—C37—C32—C33−179.12 (16)C4—C41—C42—C4312.8 (2)
C36—C37—C32—C331.3 (3)C47—C42—C43—C44−0.6 (3)
N2—C37—C32—C31−0.42 (19)C41—C42—C43—C44178.27 (16)
C36—C37—C32—C31179.96 (16)C42—C43—C44—C450.5 (3)
N2—C38—C31—C320.32 (19)C43—C44—C45—C460.0 (3)
N2—C38—C31—C3−176.61 (15)C44—C45—C46—C47−0.4 (3)
C33—C32—C31—C38178.46 (19)C45—C46—C47—C420.3 (3)
C37—C32—C31—C380.07 (18)C43—C42—C47—C460.3 (3)
C33—C32—C31—C3−4.7 (3)C41—C42—C47—C46−178.69 (16)
C37—C32—C31—C3176.94 (15)C2—C5—C51—C5663.99 (19)
C4—O1—C3—C2−5.21 (17)C4—C5—C51—C56−48.45 (19)
C4—O1—C3—C31176.25 (13)C2—C5—C51—C52−113.25 (17)
C38—C31—C3—C2−23.4 (3)C4—C5—C51—C52134.30 (16)
C32—C31—C3—C2160.29 (17)C56—C51—C52—C53−2.1 (3)
C38—C31—C3—O1154.78 (15)C5—C51—C52—C53175.27 (17)
C32—C31—C3—O1−21.5 (2)C51—C52—C53—C54−0.1 (3)
O1—C3—C2—C1177.33 (14)C52—C53—C54—C552.1 (3)
C31—C3—C2—C1−4.4 (3)C52—C53—C54—C6−174.53 (19)
O1—C3—C2—C5−5.75 (18)C53—C54—C55—C56−1.9 (3)
C31—C3—C2—C5172.48 (16)C6—C54—C55—C56174.67 (17)
C3—C2—C5—C51−109.41 (15)C52—C51—C56—C552.2 (2)
C1—C2—C5—C5167.58 (19)C5—C51—C56—C55−175.12 (14)
C3—C2—C5—C412.92 (16)C54—C55—C56—C51−0.2 (3)
C1—C2—C5—C4−170.09 (15)C53—C54—C6—C8−133.9 (2)
C3—O1—C4—C41−108.29 (13)C55—C54—C6—C849.6 (3)
C3—O1—C4—C513.55 (15)C53—C54—C6—C799.9 (2)
C51—C5—C4—O1104.52 (14)C55—C54—C6—C7−76.6 (2)
D—H···AD—HH···AD···AD—H···A
C33—H33···O10.961 (16)2.569 (15)3.081 (2)113.5 (11)
N2—H2···N1i0.91 (2)2.09 (2)2.973 (2)165.2 (17)
C56—H56···O2ii0.978 (15)2.411 (16)3.371 (2)166.9 (13)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
N2—H2⋯N1i 0.91 (2)2.09 (2)2.973 (2)165.2 (17)
C56—H56⋯O2ii 0.978 (15)2.411 (16)3.371 (2)166.9 (13)

Symmetry codes: (i) ; (ii) .

  6 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.  Taking the aromaticity out of aromatic interactions.

Authors:  Jacob W G Bloom; Steven E Wheeler
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-05       Impact factor: 15.336

3.  (±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-4,5-dihydro-furan-3-carbonitrile.

Authors:  J Suresh; R Vishnupriya; P Gunasekaran; S Perumal; P L Nilantha Lakshman
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-28

4.  (±)-trans-5-Benzoyl-4-(3-bromo-phen-yl)-2-(1H-indol-3-yl)-4,5-dihydro-furan-3-carbonitrile.

Authors:  J Suresh; R Vishnupriya; P Gunasekaran; S Perumal; P L Nilantha Lakshman
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-10

5.  5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methyl-phen-yl)-4,5-dihydro-furan-3-carbonitrile.

Authors:  J Suresh; R Vishnupriya; P Gunasekaran; S Perumal; P L Nilantha Lakshman
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-21

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  Crystal structure of 5-benzoyl-2,4-di-phenyl-4,5-di-hydro-furan-3-carbo-nitrile.

Authors:  V Rajni Swamy; R V Krishnakumar; S Sivakumar; N Srinivasan; R Ranjith Kumar
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-08-15
  1 in total

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