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In the title compound, [Sn(C6H5)3(C7H5N2O4)], the nitro and amino groups are coplanar with the attached benzene ring. The mol­ecules are linked by inter­molecular N—H...O inter­actions, forming one-dimensional chains along [010]. In addition, the crystal structure is further stabilized by inter­molecular C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055735/ng2189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055735/ng2189Isup2.hkl
Contains datablock I

CCDC reference: 636757

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.071
  • Data-to-parameter ratio = 33.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.76 mm
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(2-Amino-5-nitrobenzoato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C7H5N2O4)]F(000) = 2128
Mr = 531.12Dx = 1.558 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8682 reflections
a = 11.0062 (4) Åθ = 2.3–35.0°
b = 15.8022 (4) ŵ = 1.16 mm1
c = 26.5645 (8) ÅT = 100 K
β = 101.415 (2)°Block, yellow
V = 4528.8 (2) Å30.76 × 0.73 × 0.40 mm
Z = 8
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
9913 independent reflections
Radiation source: fine-focus sealed tube9343 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.33 pixels mm-1θmax = 35.0°, θmin = 2.3°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2525
Tmin = 0.482, Tmax = 0.657l = 4242
47389 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.24 w = 1/[σ2(Fo2) + (0.0165P)2 + 9.0039P]
where P = (Fo2 + 2Fc2)/3
9913 reflections(Δ/σ)max < 0.001
297 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 1.18 e Å3
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Analysis found for C25H20N2O4Sn1: C, 56.41; H, 3.48; N, 5.23; Sn, 22.03%. Calculated for C25H20N2O4Sn1: C, 56.53; H, 3.80; N, 5.27; Sn, 22.35%. FTIR as KBr disc (cm-1): v(COO)as 1618, v(COO)s 1310, v(O—Sn—O) 641, v(Sn—O) 443. 1H-NMR: δ: phenyl protons 7.95–7.97 (6H, d, J= 6.5 Hz); 8.73 - 8.74 (9H, m); benzene 6.81–6.83 (1H, d, J = 9.2 Hz); 8.08–8.09 (1H, dd, J = 9.2 Hz); 8.73 - 8.74 (1H, d, J = 2.9 Hz) p.p.m.. 13C-NMR: δ: phenyl carbons Cipro 142.87 (839.31 Hz), Cortho 136.11 (45.60 Hz), Cmeta 128.43, Cpara 129.03 (18.37 Hz); benzene 112.77, 115.75, 127.72, 127.97, 134.89, 155.92; COO 169.52 p.p.m.. 119Sn-NMR: δ: -265.89 p.p.m..

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.112679 (9)0.244403 (6)0.069146 (4)0.01464 (3)
O10.00363 (11)0.26594 (7)0.12337 (4)0.0180 (2)
O20.00484 (11)0.12533 (7)0.12494 (4)0.0181 (2)
O30.31293 (16)0.37037 (9)0.28068 (6)0.0325 (3)
O40.2258 (2)0.42822 (9)0.22323 (7)0.0446 (5)
N10.09814 (14)0.04650 (8)0.19545 (5)0.0184 (2)
N20.25082 (16)0.36573 (9)0.24696 (6)0.0249 (3)
C10.13134 (13)0.12438 (9)0.20792 (5)0.0140 (2)
C20.20040 (14)0.13400 (9)0.24725 (6)0.0161 (2)
H2A0.21970.08640.26470.019*
C30.23928 (15)0.21184 (10)0.26011 (6)0.0174 (2)
H3A0.28650.21710.28540.021*
C40.20694 (15)0.28376 (9)0.23463 (6)0.0172 (2)
C50.13682 (14)0.27783 (9)0.19680 (6)0.0159 (2)
H5A0.11530.32640.18080.019*
C60.09880 (13)0.19848 (9)0.18287 (5)0.0136 (2)
C70.02602 (13)0.19348 (9)0.14166 (5)0.0145 (2)
C80.27865 (14)0.18760 (9)0.10924 (5)0.0156 (2)
C90.28284 (14)0.10366 (10)0.12607 (6)0.0189 (3)
H9A0.21130.07090.11950.023*
C100.39291 (17)0.06872 (12)0.15259 (7)0.0249 (3)
H10A0.39470.01290.16370.030*
C110.50005 (17)0.11719 (14)0.16242 (8)0.0304 (4)
H11A0.57380.09380.18010.036*
C120.49732 (17)0.20053 (13)0.14589 (8)0.0287 (4)
H12A0.56920.23300.15260.034*
C130.38748 (16)0.23574 (11)0.11923 (6)0.0214 (3)
H13A0.38630.29150.10800.026*
C140.14104 (14)0.37306 (9)0.05104 (6)0.0165 (2)
C150.18912 (18)0.43166 (11)0.08936 (6)0.0232 (3)
H15A0.20290.41570.12370.028*
C160.21640 (18)0.51387 (11)0.07614 (7)0.0264 (3)
H16A0.24780.55270.10170.032*
C170.19691 (16)0.53775 (10)0.02506 (7)0.0230 (3)
H17A0.21810.59200.01640.028*
C180.14618 (16)0.48139 (10)0.01304 (6)0.0209 (3)
H18A0.13050.49830.04730.025*
C190.11848 (14)0.39903 (10)0.00009 (6)0.0177 (2)
H19A0.08460.36110.02580.021*
C200.00326 (13)0.18414 (9)0.00429 (6)0.0147 (2)
C210.10563 (15)0.22362 (10)0.02053 (6)0.0198 (3)
H21A0.13020.27400.00750.024*
C220.17782 (16)0.18856 (11)0.06445 (7)0.0235 (3)
H22A0.25080.21510.08040.028*
C230.14084 (17)0.11379 (11)0.08455 (6)0.0223 (3)
H23A0.18820.09070.11430.027*
C240.03284 (16)0.07369 (10)0.06004 (6)0.0210 (3)
H24A0.00830.02340.07320.025*
C250.03870 (15)0.10845 (9)0.01588 (6)0.0177 (2)
H25A0.11070.08110.00040.021*
H1A0.124 (2)0.0035 (17)0.2082 (10)0.029 (6)*
H1B0.059 (2)0.0420 (16)0.1715 (10)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01559 (5)0.01435 (4)0.01466 (4)0.00294 (3)0.00464 (3)0.00077 (3)
O10.0218 (5)0.0146 (4)0.0201 (5)0.0014 (4)0.0098 (4)0.0013 (4)
O20.0190 (5)0.0173 (5)0.0194 (5)0.0007 (4)0.0072 (4)0.0020 (4)
O30.0476 (9)0.0268 (6)0.0296 (7)0.0070 (6)0.0234 (6)0.0028 (5)
O40.0783 (13)0.0164 (6)0.0507 (10)0.0073 (7)0.0412 (9)0.0044 (6)
N10.0239 (6)0.0140 (5)0.0180 (5)0.0008 (4)0.0059 (5)0.0008 (4)
N20.0345 (8)0.0194 (6)0.0238 (7)0.0039 (5)0.0132 (6)0.0017 (5)
C10.0145 (6)0.0149 (5)0.0120 (5)0.0008 (4)0.0011 (4)0.0009 (4)
C20.0166 (6)0.0179 (6)0.0142 (6)0.0015 (5)0.0039 (5)0.0022 (4)
C30.0185 (6)0.0193 (6)0.0151 (6)0.0007 (5)0.0051 (5)0.0007 (4)
C40.0210 (7)0.0159 (6)0.0156 (6)0.0018 (5)0.0056 (5)0.0002 (4)
C50.0205 (6)0.0121 (5)0.0161 (6)0.0026 (4)0.0064 (5)0.0012 (4)
C60.0135 (5)0.0138 (5)0.0133 (5)0.0002 (4)0.0023 (4)0.0008 (4)
C70.0129 (6)0.0166 (6)0.0139 (5)0.0010 (4)0.0026 (4)0.0005 (4)
C80.0149 (6)0.0194 (6)0.0129 (5)0.0026 (4)0.0038 (4)0.0021 (4)
C90.0144 (6)0.0195 (6)0.0229 (7)0.0018 (5)0.0043 (5)0.0021 (5)
C100.0202 (7)0.0256 (7)0.0283 (8)0.0017 (6)0.0035 (6)0.0034 (6)
C110.0174 (7)0.0404 (10)0.0304 (9)0.0017 (7)0.0023 (6)0.0062 (7)
C120.0186 (7)0.0385 (10)0.0266 (8)0.0094 (7)0.0016 (6)0.0041 (7)
C130.0200 (7)0.0248 (7)0.0193 (6)0.0080 (5)0.0034 (5)0.0015 (5)
C140.0169 (6)0.0169 (6)0.0160 (6)0.0026 (5)0.0041 (5)0.0004 (4)
C150.0308 (8)0.0199 (7)0.0169 (6)0.0051 (6)0.0005 (6)0.0001 (5)
C160.0288 (8)0.0179 (7)0.0292 (8)0.0041 (6)0.0021 (7)0.0020 (6)
C170.0201 (7)0.0157 (6)0.0337 (9)0.0006 (5)0.0067 (6)0.0055 (6)
C180.0208 (7)0.0229 (7)0.0203 (7)0.0045 (5)0.0074 (5)0.0058 (5)
C190.0175 (6)0.0209 (6)0.0155 (6)0.0000 (5)0.0052 (5)0.0003 (5)
C200.0135 (6)0.0150 (5)0.0159 (6)0.0011 (4)0.0033 (4)0.0002 (4)
C210.0173 (6)0.0177 (6)0.0237 (7)0.0030 (5)0.0021 (5)0.0007 (5)
C220.0183 (7)0.0244 (7)0.0249 (7)0.0008 (5)0.0025 (6)0.0032 (6)
C230.0235 (7)0.0234 (7)0.0180 (6)0.0057 (6)0.0006 (5)0.0007 (5)
C240.0235 (7)0.0178 (6)0.0219 (7)0.0021 (5)0.0046 (6)0.0039 (5)
C250.0166 (6)0.0161 (6)0.0199 (6)0.0010 (5)0.0026 (5)0.0012 (5)
Geometric parameters (Å, º) top
Sn1—O12.0774 (11)C11—C121.387 (3)
Sn1—C202.1224 (15)C11—H11A0.9300
Sn1—C82.1230 (15)C12—C131.391 (3)
Sn1—C142.1264 (15)C12—H12A0.9300
O1—C71.3101 (17)C13—H13A0.9300
O2—C71.2378 (18)C14—C191.394 (2)
O3—N21.2318 (19)C14—C151.400 (2)
O4—N21.232 (2)C15—C161.394 (2)
N1—C11.3438 (19)C15—H15A0.9300
N1—H1A0.84 (3)C16—C171.384 (3)
N1—H1B0.84 (3)C16—H16A0.9300
N2—C41.443 (2)C17—C181.380 (3)
C1—C21.416 (2)C17—H17A0.9300
C1—C61.4271 (19)C18—C191.395 (2)
C2—C31.368 (2)C18—H18A0.9300
C2—H2A0.9300C19—H19A0.9300
C3—C41.404 (2)C20—C211.395 (2)
C3—H3A0.9300C20—C251.397 (2)
C4—C51.386 (2)C21—C221.390 (2)
C5—C61.395 (2)C21—H21A0.9300
C5—H5A0.9300C22—C231.390 (3)
C6—C71.481 (2)C22—H22A0.9300
C8—C91.398 (2)C23—C241.390 (2)
C8—C131.399 (2)C23—H23A0.9300
C9—C101.390 (2)C24—C251.390 (2)
C9—H9A0.9300C24—H24A0.9300
C10—C111.387 (3)C25—H25A0.9300
C10—H10A0.9300
O1—Sn1—C20108.88 (5)C12—C11—H11A120.0
O1—Sn1—C8106.21 (5)C10—C11—H11A120.0
C20—Sn1—C8120.75 (5)C11—C12—C13120.23 (16)
O1—Sn1—C1497.53 (5)C11—C12—H12A119.9
C20—Sn1—C14109.30 (6)C13—C12—H12A119.9
C8—Sn1—C14111.56 (6)C12—C13—C8120.28 (16)
C7—O1—Sn1109.54 (9)C12—C13—H13A119.9
C1—N1—H1A120.9 (18)C8—C13—H13A119.9
C1—N1—H1B118.0 (18)C19—C14—C15118.86 (14)
H1A—N1—H1B121 (3)C19—C14—Sn1119.75 (11)
O4—N2—O3122.48 (15)C15—C14—Sn1121.28 (11)
O4—N2—C4119.00 (14)C16—C15—C14120.17 (16)
O3—N2—C4118.52 (14)C16—C15—H15A119.9
N1—C1—C2119.47 (13)C14—C15—H15A119.9
N1—C1—C6122.07 (13)C17—C16—C15120.12 (16)
C2—C1—C6118.47 (13)C17—C16—H16A119.9
C3—C2—C1121.39 (13)C15—C16—H16A119.9
C3—C2—H2A119.3C18—C17—C16120.32 (15)
C1—C2—H2A119.3C18—C17—H17A119.8
C2—C3—C4119.05 (14)C16—C17—H17A119.8
C2—C3—H3A120.5C17—C18—C19119.83 (15)
C4—C3—H3A120.5C17—C18—H18A120.1
C5—C4—C3121.69 (14)C19—C18—H18A120.1
C5—C4—N2119.00 (13)C14—C19—C18120.63 (15)
C3—C4—N2119.28 (14)C14—C19—H19A119.7
C4—C5—C6119.50 (13)C18—C19—H19A119.7
C4—C5—H5A120.3C21—C20—C25118.71 (14)
C6—C5—H5A120.3C21—C20—Sn1118.64 (11)
C5—C6—C1119.86 (13)C25—C20—Sn1122.59 (11)
C5—C6—C7118.60 (12)C22—C21—C20120.87 (15)
C1—C6—C7121.54 (12)C22—C21—H21A119.6
O2—C7—O1121.41 (13)C20—C21—H21A119.6
O2—C7—C6122.60 (13)C23—C22—C21119.93 (15)
O1—C7—C6115.99 (12)C23—C22—H22A120.0
C9—C8—C13118.85 (15)C21—C22—H22A120.0
C9—C8—Sn1122.17 (11)C24—C23—C22119.72 (15)
C13—C8—Sn1118.98 (12)C24—C23—H23A120.1
C10—C9—C8120.63 (15)C22—C23—H23A120.1
C10—C9—H9A119.7C25—C24—C23120.28 (15)
C8—C9—H9A119.7C25—C24—H24A119.9
C11—C10—C9119.96 (17)C23—C24—H24A119.9
C11—C10—H10A120.0C24—C25—C20120.49 (14)
C9—C10—H10A120.0C24—C25—H25A119.8
C12—C11—C10120.04 (17)C20—C25—H25A119.8
C20—Sn1—O1—C767.42 (11)C8—C9—C10—C110.2 (3)
C8—Sn1—O1—C764.04 (11)C9—C10—C11—C120.1 (3)
C14—Sn1—O1—C7179.16 (10)C10—C11—C12—C130.3 (3)
N1—C1—C2—C3178.02 (15)C11—C12—C13—C80.5 (3)
C6—C1—C2—C32.2 (2)C9—C8—C13—C120.6 (2)
C1—C2—C3—C41.7 (2)Sn1—C8—C13—C12179.32 (14)
C2—C3—C4—C50.1 (2)O1—Sn1—C14—C19129.44 (12)
C2—C3—C4—N2178.15 (15)C20—Sn1—C14—C1916.36 (14)
O4—N2—C4—C50.6 (3)C8—Sn1—C14—C19119.76 (12)
O3—N2—C4—C5179.91 (17)O1—Sn1—C14—C1554.39 (14)
O4—N2—C4—C3177.50 (19)C20—Sn1—C14—C15167.47 (13)
O3—N2—C4—C32.0 (3)C8—Sn1—C14—C1556.40 (15)
C3—C4—C5—C61.1 (2)C19—C14—C15—C161.5 (3)
N2—C4—C5—C6177.01 (15)Sn1—C14—C15—C16174.71 (14)
C4—C5—C6—C10.6 (2)C14—C15—C16—C170.5 (3)
C4—C5—C6—C7178.83 (14)C15—C16—C17—C182.4 (3)
N1—C1—C6—C5179.21 (14)C16—C17—C18—C192.3 (3)
C2—C1—C6—C51.0 (2)C15—C14—C19—C181.6 (2)
N1—C1—C6—C70.2 (2)Sn1—C14—C19—C18174.68 (12)
C2—C1—C6—C7179.59 (13)C17—C18—C19—C140.3 (2)
Sn1—O1—C7—O23.42 (18)O1—Sn1—C20—C2156.31 (13)
Sn1—O1—C7—C6177.01 (10)C8—Sn1—C20—C21179.45 (11)
C5—C6—C7—O2175.56 (14)C14—Sn1—C20—C2149.14 (13)
C1—C6—C7—O23.8 (2)O1—Sn1—C20—C25126.59 (12)
C5—C6—C7—O14.0 (2)C8—Sn1—C20—C253.45 (14)
C1—C6—C7—O1176.62 (13)C14—Sn1—C20—C25127.96 (12)
O1—Sn1—C8—C973.72 (12)C25—C20—C21—C220.1 (2)
C20—Sn1—C8—C950.69 (14)Sn1—C20—C21—C22177.27 (13)
C14—Sn1—C8—C9178.88 (11)C20—C21—C22—C230.9 (3)
O1—Sn1—C8—C13106.22 (12)C21—C22—C23—C241.1 (3)
C20—Sn1—C8—C13129.38 (12)C22—C23—C24—C250.6 (3)
C14—Sn1—C8—C131.06 (13)C23—C24—C25—C200.2 (2)
C13—C8—C9—C100.5 (2)C21—C20—C25—C240.5 (2)
Sn1—C8—C9—C10179.46 (13)Sn1—C20—C25—C24176.61 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.84 (2)2.03 (2)2.681 (2)134 (2)
C5—H5A···O10.932.402.725 (2)101
C9—H9A···O20.932.463.073 (2)124
N1—H1A···O3i0.83 (3)2.25 (3)3.058 (2)162 (2)
C3—H3A···Cg2ii0.932.773.616 (2)152
C12—H12A···Cg1iii0.933.133.823 (2)133
C13—H13A···Cg4iv0.933.103.661 (2)120
C17—H17A···Cg4v0.933.153.804 (2)129
C19—H19A···Cg2iv0.933.003.681 (2)131
C25—H25A···Cg3iv0.932.883.544 (2)129
Symmetry codes: (i) x1/2, y1/2, z+1/2; (ii) x, y, z+1/2; (iii) x+1, y, z; (iv) x+1/2, y+1/2, z; (v) x+1/2, y+1/2, z.
 

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