Literature DB >> 22064934

catena-Poly[[triphenyl-tin(IV)]-μ-5-amino-2-nitro-benzoato-κO:O].

Yip-Foo Win, Chen-Shang Choong, Siang-Guan Teoh, Ching Kheng Quah, Hoong-Kun Fun.   

Abstract

The title compound, [Sn(C(6)H(5))(3)(C(7)H(5)N(2)O(4))](n), forms polymeric chains along [010]. The Sn(IV) ion is five-coordinated in a distorted trigonal-bipyramidal geometry by two monodentate carboxyl-ate groups and three phenyl rings. The axial sites are occupied by the O atoms of two symmetry-related carboxyl-ate groups [O-Sn-O = 170.88 (3)°]. The benzene ring of the 5-amino-2-nitro-benzoate ligand forms dihedral angles of 82.92 (6), 81.10 (6) and 83.54 (6)° with respect to the three phenyl rings. In the crystal, the chains are linked by inter-molecular N-H⋯O and weak C-H⋯O inter-actions into a three-dimensional network. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID: 22064934      PMCID: PMC3200871          DOI: 10.1107/S1600536811033332

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


Related literature

For general background to and the coordination environment of triphenyl­tin(IV) carboxyl­ate complexes, see: Yeap & Teoh (2003 ▶); Win et al. (2006 ▶, 2008 ▶, 2011a ▶,b ▶,c ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Sn(C6H5)3(C7H5N2O4)] M = 531.12 Monoclinic, a = 10.9752 (1) Å b = 11.8342 (1) Å c = 17.4160 (2) Å β = 102.164 (1)° V = 2211.25 (4) Å3 Z = 4 Mo Kα radiation μ = 1.19 mm−1 T = 100 K 0.37 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.671, T max = 0.783 27219 measured reflections 7981 independent reflections 7370 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.018 wR(F 2) = 0.046 S = 1.07 7981 reflections 297 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.51 e Å−3 Δρmin = −0.54 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033332/lh5316sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033332/lh5316Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Sn(C6H5)3(C7H5N2O4)]F(000) = 1064
Mr = 531.12Dx = 1.595 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9281 reflections
a = 10.9752 (1) Åθ = 2.4–32.7°
b = 11.8342 (1) ŵ = 1.19 mm1
c = 17.4160 (2) ÅT = 100 K
β = 102.164 (1)°Block, yellow
V = 2211.25 (4) Å30.37 × 0.25 × 0.22 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer7981 independent reflections
Radiation source: fine-focus sealed tube7370 reflections with I > 2σ(I)
graphiteRint = 0.017
φ and ω scansθmax = 32.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→16
Tmin = 0.671, Tmax = 0.783k = −17→15
27219 measured reflectionsl = −24→26
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.018Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0187P)2 + 0.9636P] where P = (Fo2 + 2Fc2)/3
7981 reflections(Δ/σ)max = 0.003
297 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.54 e Å3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Sn10.980205 (6)0.157183 (6)0.217102 (4)0.01124 (2)
O10.93081 (8)0.32432 (7)0.16122 (5)0.01487 (14)
O20.97650 (7)0.46996 (7)0.24440 (4)0.01352 (14)
O30.70740 (8)0.38800 (8)0.21137 (5)0.02102 (17)
O40.53208 (8)0.43580 (10)0.13585 (6)0.0329 (2)
N10.89051 (11)0.67399 (10)−0.04786 (6)0.0218 (2)
N20.64692 (9)0.43960 (9)0.15452 (6)0.01829 (18)
C10.87574 (10)0.17504 (9)0.30535 (6)0.01377 (18)
C20.89877 (11)0.25962 (10)0.36218 (7)0.0193 (2)
H2A0.95970.31580.35990.023*
C30.83296 (13)0.26235 (12)0.42251 (7)0.0243 (2)
H3A0.84960.31990.46130.029*
C40.74309 (12)0.18074 (12)0.42582 (7)0.0247 (2)
H4A0.69880.18230.46720.030*
C50.71792 (11)0.09704 (12)0.36888 (7)0.0224 (2)
H5A0.65570.04190.37080.027*
C60.78424 (10)0.09427 (10)0.30890 (7)0.0176 (2)
H6A0.76700.03680.27000.021*
C70.86334 (10)0.08532 (9)0.11625 (6)0.01378 (18)
C80.73920 (10)0.12127 (11)0.09743 (7)0.0191 (2)
H8A0.71180.17960.12720.023*
C90.65528 (12)0.07180 (14)0.03508 (7)0.0276 (3)
H9A0.57120.09690.02220.033*
C100.69493 (13)−0.01430 (14)−0.00817 (8)0.0293 (3)
H10A0.6375−0.0486−0.05020.035*
C110.81737 (14)−0.05009 (11)0.00968 (7)0.0257 (3)
H11A0.8442−0.1089−0.02000.031*
C120.90166 (12)0.00017 (10)0.07139 (7)0.0186 (2)
H12A0.9861−0.02390.08300.022*
C131.17373 (10)0.19205 (10)0.23296 (6)0.01591 (19)
C141.25426 (11)0.11915 (12)0.20473 (7)0.0212 (2)
H14A1.22240.05270.17700.025*
C151.38145 (12)0.14349 (14)0.21712 (8)0.0290 (3)
H15A1.43560.09380.19740.035*
C161.42905 (12)0.23968 (14)0.25801 (10)0.0352 (4)
H16A1.51550.25610.26610.042*
C171.34983 (13)0.31200 (13)0.28711 (12)0.0383 (4)
H17A1.38250.37740.31580.046*
C181.22256 (11)0.28880 (11)0.27429 (9)0.0271 (3)
H18A1.16870.33910.29380.032*
C190.92115 (9)0.42633 (9)0.18082 (6)0.01185 (17)
C200.84255 (9)0.49904 (9)0.11779 (6)0.01259 (17)
C210.90148 (10)0.55602 (9)0.06630 (6)0.01415 (18)
H21A0.98950.55120.07300.017*
C220.83273 (11)0.62117 (10)0.00411 (6)0.01612 (19)
C230.70317 (11)0.63147 (11)−0.00281 (7)0.0196 (2)
H23A0.65620.6784−0.04250.024*
C240.64407 (10)0.57407 (11)0.04748 (7)0.0194 (2)
H24A0.55640.58060.04200.023*
C250.71282 (10)0.50604 (10)0.10674 (6)0.01502 (19)
H1N10.8472 (16)0.6975 (16)−0.0914 (11)0.028 (4)*
H2N10.9684 (18)0.6650 (15)−0.0455 (11)0.032 (5)*
U11U22U33U12U13U23
Sn10.01332 (3)0.00974 (4)0.01053 (3)−0.00065 (2)0.00225 (2)−0.00024 (2)
O10.0199 (3)0.0093 (4)0.0152 (3)0.0003 (3)0.0032 (3)0.0005 (3)
O20.0169 (3)0.0107 (4)0.0122 (3)−0.0003 (3)0.0013 (2)0.0001 (3)
O30.0179 (4)0.0240 (5)0.0210 (4)0.0006 (3)0.0037 (3)0.0069 (3)
O40.0126 (4)0.0446 (7)0.0399 (5)−0.0017 (4)0.0019 (4)0.0139 (5)
N10.0300 (5)0.0202 (5)0.0158 (4)0.0032 (4)0.0060 (4)0.0064 (4)
N20.0147 (4)0.0192 (5)0.0207 (4)0.0001 (3)0.0032 (3)0.0007 (4)
C10.0163 (4)0.0126 (5)0.0127 (4)0.0008 (3)0.0035 (3)0.0008 (3)
C20.0264 (5)0.0143 (5)0.0187 (5)−0.0024 (4)0.0080 (4)−0.0027 (4)
C30.0340 (6)0.0220 (6)0.0194 (5)0.0012 (5)0.0109 (5)−0.0050 (4)
C40.0279 (6)0.0298 (7)0.0198 (5)0.0035 (5)0.0125 (4)0.0028 (5)
C50.0205 (5)0.0256 (6)0.0225 (5)−0.0029 (4)0.0076 (4)0.0041 (5)
C60.0179 (4)0.0177 (5)0.0169 (5)−0.0020 (4)0.0033 (4)−0.0007 (4)
C70.0180 (4)0.0110 (5)0.0121 (4)−0.0022 (4)0.0025 (3)0.0001 (3)
C80.0170 (4)0.0239 (6)0.0164 (5)−0.0026 (4)0.0037 (4)−0.0024 (4)
C90.0190 (5)0.0422 (8)0.0203 (5)−0.0086 (5)0.0014 (4)−0.0037 (5)
C100.0326 (6)0.0358 (8)0.0186 (5)−0.0178 (6)0.0030 (5)−0.0081 (5)
C110.0426 (7)0.0173 (6)0.0176 (5)−0.0072 (5)0.0075 (5)−0.0059 (4)
C120.0282 (5)0.0120 (5)0.0155 (5)0.0010 (4)0.0041 (4)−0.0004 (4)
C130.0152 (4)0.0144 (5)0.0174 (5)−0.0005 (4)0.0019 (3)0.0052 (4)
C140.0192 (5)0.0284 (7)0.0166 (5)0.0016 (4)0.0052 (4)0.0017 (4)
C150.0184 (5)0.0444 (9)0.0259 (6)0.0052 (5)0.0082 (4)0.0084 (6)
C160.0165 (5)0.0367 (9)0.0500 (9)−0.0036 (5)0.0012 (5)0.0195 (7)
C170.0202 (6)0.0196 (7)0.0683 (11)−0.0053 (5)−0.0064 (6)0.0053 (7)
C180.0180 (5)0.0140 (6)0.0453 (8)−0.0004 (4)−0.0020 (5)0.0000 (5)
C190.0123 (4)0.0114 (5)0.0124 (4)−0.0002 (3)0.0039 (3)0.0015 (3)
C200.0154 (4)0.0096 (5)0.0120 (4)0.0007 (3)0.0013 (3)−0.0010 (3)
C210.0175 (4)0.0120 (5)0.0126 (4)0.0011 (4)0.0023 (3)0.0004 (3)
C220.0231 (5)0.0122 (5)0.0125 (4)0.0012 (4)0.0025 (4)0.0000 (4)
C230.0221 (5)0.0173 (5)0.0170 (5)0.0038 (4)−0.0017 (4)0.0031 (4)
C240.0163 (4)0.0194 (6)0.0202 (5)0.0030 (4)−0.0012 (4)0.0016 (4)
C250.0154 (4)0.0137 (5)0.0152 (4)0.0002 (4)0.0016 (3)0.0003 (4)
Sn1—C12.1129 (11)C9—C101.390 (2)
Sn1—C72.1222 (10)C9—H9A0.9500
Sn1—C132.1239 (11)C10—C111.381 (2)
Sn1—O12.2205 (8)C10—H10A0.9500
Sn1—O2i2.3345 (8)C11—C121.3949 (17)
O1—C191.2651 (13)C11—H11A0.9500
O2—C191.2563 (12)C12—H12A0.9500
O2—Sn1ii2.3345 (8)C13—C141.3965 (17)
O3—N21.2315 (13)C13—C181.3978 (18)
O4—N21.2344 (12)C14—C151.3968 (17)
N1—C221.3616 (15)C14—H14A0.9500
N1—H1N10.852 (18)C15—C161.385 (2)
N1—H2N10.853 (19)C15—H15A0.9500
N2—C251.4447 (15)C16—C171.390 (2)
C1—C21.3928 (16)C16—H16A0.9500
C1—C61.3972 (16)C17—C181.3947 (18)
C2—C31.3952 (17)C17—H17A0.9500
C2—H2A0.9500C18—H18A0.9500
C3—C41.390 (2)C19—C201.5135 (14)
C3—H3A0.9500C20—C211.3862 (15)
C4—C51.3876 (19)C20—C251.3984 (14)
C4—H4A0.9500C21—C221.4116 (15)
C5—C61.3937 (16)C21—H21A0.9500
C5—H5A0.9500C22—C231.4068 (16)
C6—H6A0.9500C23—C241.3742 (17)
C7—C121.3933 (16)C23—H23A0.9500
C7—C81.3988 (15)C24—C251.3982 (15)
C8—C91.3960 (16)C24—H24A0.9500
C8—H8A0.9500
C1—Sn1—C7108.43 (4)C9—C10—H10A119.9
C1—Sn1—C13124.55 (4)C10—C11—C12119.92 (12)
C7—Sn1—C13126.79 (4)C10—C11—H11A120.0
C1—Sn1—O196.31 (4)C12—C11—H11A120.0
C7—Sn1—O186.85 (4)C7—C12—C11120.73 (11)
C13—Sn1—O191.67 (4)C7—C12—H12A119.6
C1—Sn1—O2i89.71 (4)C11—C12—H12A119.6
C7—Sn1—O2i84.74 (3)C14—C13—C18119.01 (11)
C13—Sn1—O2i90.55 (4)C14—C13—Sn1121.60 (9)
O1—Sn1—O2i170.88 (3)C18—C13—Sn1119.37 (9)
C19—O1—Sn1139.32 (7)C13—C14—C15120.28 (13)
C19—O2—Sn1ii132.42 (7)C13—C14—H14A119.9
C22—N1—H1N1119.4 (12)C15—C14—H14A119.9
C22—N1—H2N1120.9 (13)C16—C15—C14120.35 (13)
H1N1—N1—H2N1116.6 (17)C16—C15—H15A119.8
O3—N2—O4122.76 (11)C14—C15—H15A119.8
O3—N2—C25118.84 (9)C15—C16—C17119.76 (12)
O4—N2—C25118.39 (10)C15—C16—H16A120.1
C2—C1—C6119.00 (10)C17—C16—H16A120.1
C2—C1—Sn1122.94 (8)C16—C17—C18120.20 (15)
C6—C1—Sn1117.97 (8)C16—C17—H17A119.9
C1—C2—C3120.43 (11)C18—C17—H17A119.9
C1—C2—H2A119.8C17—C18—C13120.40 (14)
C3—C2—H2A119.8C17—C18—H18A119.8
C4—C3—C2119.97 (12)C13—C18—H18A119.8
C4—C3—H3A120.0O2—C19—O1125.29 (10)
C2—C3—H3A120.0O2—C19—C20120.10 (10)
C5—C4—C3120.16 (11)O1—C19—C20114.46 (9)
C5—C4—H4A119.9C21—C20—C25118.85 (9)
C3—C4—H4A119.9C21—C20—C19118.26 (9)
C4—C5—C6119.71 (12)C25—C20—C19122.80 (9)
C4—C5—H5A120.1C20—C21—C22121.02 (10)
C6—C5—H5A120.1C20—C21—H21A119.5
C5—C6—C1120.71 (11)C22—C21—H21A119.5
C5—C6—H6A119.6N1—C22—C23120.48 (11)
C1—C6—H6A119.6N1—C22—C21120.82 (11)
C12—C7—C8118.86 (10)C23—C22—C21118.70 (10)
C12—C7—Sn1123.56 (8)C24—C23—C22120.46 (10)
C8—C7—Sn1117.46 (8)C24—C23—H23A119.8
C9—C8—C7120.34 (12)C22—C23—H23A119.8
C9—C8—H8A119.8C23—C24—C25120.09 (10)
C7—C8—H8A119.8C23—C24—H24A120.0
C10—C9—C8119.88 (12)C25—C24—H24A120.0
C10—C9—H9A120.1C24—C25—C20120.74 (10)
C8—C9—H9A120.1C24—C25—N2118.73 (10)
C11—C10—C9120.25 (11)C20—C25—N2120.48 (9)
C11—C10—H10A119.9
C1—Sn1—O1—C1944.23 (11)O2i—Sn1—C13—C1445.61 (9)
C7—Sn1—O1—C19152.44 (11)C1—Sn1—C13—C18−42.79 (11)
C13—Sn1—O1—C19−80.80 (11)C7—Sn1—C13—C18143.36 (9)
C7—Sn1—C1—C2−150.32 (9)O1—Sn1—C13—C1856.05 (10)
C13—Sn1—C1—C234.87 (11)O2i—Sn1—C13—C18−132.81 (10)
O1—Sn1—C1—C2−61.55 (10)C18—C13—C14—C15−0.60 (18)
O2i—Sn1—C1—C2125.33 (9)Sn1—C13—C14—C15−179.01 (9)
C7—Sn1—C1—C633.28 (10)C13—C14—C15—C160.5 (2)
C13—Sn1—C1—C6−141.54 (8)C14—C15—C16—C170.3 (2)
O1—Sn1—C1—C6122.05 (8)C15—C16—C17—C18−0.9 (2)
O2i—Sn1—C1—C6−51.08 (9)C16—C17—C18—C130.8 (2)
C6—C1—C2—C31.14 (17)C14—C13—C18—C170.0 (2)
Sn1—C1—C2—C3−175.23 (9)Sn1—C13—C18—C17178.42 (12)
C1—C2—C3—C4−0.5 (2)Sn1ii—O2—C19—O1161.05 (8)
C2—C3—C4—C5−0.5 (2)Sn1ii—O2—C19—C20−14.22 (14)
C3—C4—C5—C60.8 (2)Sn1—O1—C19—O223.95 (17)
C4—C5—C6—C1−0.13 (18)Sn1—O1—C19—C20−160.54 (8)
C2—C1—C6—C5−0.84 (17)O2—C19—C20—C2184.57 (13)
Sn1—C1—C6—C5175.71 (9)O1—C19—C20—C21−91.18 (12)
C1—Sn1—C7—C12−137.16 (9)O2—C19—C20—C25−99.06 (12)
C13—Sn1—C7—C1237.51 (11)O1—C19—C20—C2585.18 (13)
O1—Sn1—C7—C12127.23 (10)C25—C20—C21—C220.66 (16)
O2i—Sn1—C7—C12−49.23 (9)C19—C20—C21—C22177.17 (10)
C1—Sn1—C7—C838.72 (10)C20—C21—C22—N1−177.84 (11)
C13—Sn1—C7—C8−146.61 (8)C20—C21—C22—C232.76 (17)
O1—Sn1—C7—C8−56.89 (9)N1—C22—C23—C24177.06 (12)
O2i—Sn1—C7—C8126.65 (9)C21—C22—C23—C24−3.54 (18)
C12—C7—C8—C90.47 (18)C22—C23—C24—C250.88 (19)
Sn1—C7—C8—C9−175.60 (10)C23—C24—C25—C202.66 (18)
C7—C8—C9—C100.5 (2)C23—C24—C25—N2−175.00 (11)
C8—C9—C10—C11−0.8 (2)C21—C20—C25—C24−3.40 (16)
C9—C10—C11—C120.1 (2)C19—C20—C25—C24−179.75 (10)
C8—C7—C12—C11−1.23 (17)C21—C20—C25—N2174.21 (10)
Sn1—C7—C12—C11174.60 (9)C19—C20—C25—N2−2.13 (16)
C10—C11—C12—C70.96 (19)O3—N2—C25—C24−173.22 (11)
C1—Sn1—C13—C14135.63 (9)O4—N2—C25—C247.77 (17)
C7—Sn1—C13—C14−38.23 (11)O3—N2—C25—C209.12 (16)
O1—Sn1—C13—C14−125.54 (9)O4—N2—C25—C20−169.90 (11)
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H2N1···O1iii0.85 (2)2.498 (19)3.0619 (14)124.3 (15)
C5—H5A···O4iv0.952.403.3288 (16)167
C3—H3A···Cg2v0.952.583.4430 (14)152
C21—H21A···Cg1ii0.952.703.4669 (12)138
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 phenyl rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
N1—H2N1⋯O1i0.85 (2)2.498 (19)3.0619 (14)124.3 (15)
C5—H5A⋯O4ii0.952.403.3288 (16)167
C3—H3ACg2iii0.952.583.4430 (14)152
C21—H21ACg1iv0.952.703.4669 (12)138

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

  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.  [3-(Dimethyl-amino)benzoato]triphenyl-tin(IV).

Authors:  Yip Foo Win; Siang Guan Teoh; Sie Tiong Ha; Reza Kia; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-13

3.  (2-Chloro-4-nitro-benzoato)(methanol)triphenyl-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Sie-Tiong Ha; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-07

4.  (2-Amino-3-nitro-benzoato-κO)triphenyl-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Mei-Hsuan Heng; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13

5.  (4-Chloro-3-nitro-benzoato)triphenyl-tin(IV).

Authors:  Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
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1.  2-Amino-3-nitro-benzoic acid.

Authors:  Yip-Foo Win; Chen-Shang Choong; Siang-Guan Teoh; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-21
  1 in total

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