metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Di-μ-nicotinato-κ2N:O;κ2O:N-bis­­[aqua­bis­­(4-bromo­benz­yl)(nicotinato-κ2O,O′)tin(IV)]

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 July 2010; accepted 17 July 2010; online 24 July 2010)

Two nicotinate binding modes are observed in the dinuclear title compound, [Sn2(C7H6Br)4(C6H4NO2)4(H2O)2]: in the first, a terminal O,O′-chelating molecule binds to a water-coordinated diorganotin cation, while the second mode corresponds to an O:N-bridging molecule which binds to two cations. The two Sn atoms exist in trans-C2SnNO4 penta­gonal-bipyramidal geometries. Adjacent dinuclear units are linked by O—H⋯N hydrogen bonds, generating a linear chain, which propagates in the b-axis direction. O—H⋯O inter­actions are also observed.

Related literature

For the crystal structure of [Sn(C7H6F)2(C6H4NO2)]2, see: Yin et al. (2005[Yin, H.-D., Wang, Q.-B. & Xue, S.-C. (2005). Indian J. Chem. Sect. B, 44, 2550-2554.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn2(C7H6Br)4(C6H4NO2)4(H2O)2]

  • Mr = 1441.93

  • Monoclinic, C 2/c

  • a = 28.3754 (13) Å

  • b = 16.7568 (7) Å

  • c = 21.5642 (10) Å

  • β = 90.998 (1)°

  • V = 10251.8 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 4.16 mm−1

  • T = 100 K

  • 0.45 × 0.15 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.256, Tmax = 0.575

  • 48701 measured reflections

  • 11790 independent reflections

  • 9879 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.066

  • S = 1.18

  • 11790 reflections

  • 649 parameters

  • H-atom parameters constrained

  • Δρmax = 1.71 e Å−3

  • Δρmin = −1.35 e Å−3

Table 1
Selected bond angles (°)

C1—Sn1—C8 175.5 (1)
C27—Sn2—C34 175.2 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1w—H1w1⋯O4 0.84 1.94 2.557 (2) 129
O1w—H1w2⋯N3i 0.84 2.06 2.663 (3) 128
O2w—H2w2⋯O8 0.84 1.96 2.563 (2) 128
O2w—H2w1⋯N1ii 0.84 2.26 2.690 (3) 112
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Diorganotin dicarboxylates generally have their tin atoms in a six-coordinate skew-trapezoidal bipyramidal geometry; however, for the carboxylate unit such as the nicotinate ion that possesses a Lewis-basic nitrogen donor-atom, the nitrogen atom can participate in intermolecular coordination. This is exemplified by bis(4-fluorobenzyl)di(nicotinato)tin in which both nicotinate ions O,O'-chelate to the tin atom. However, the coordination number is raised to seven owing to the interaction of one of the two pyridyl nitrogen atoms; this tin-nitrogen bond gives rise to the formation of a chain coordination polymer (Yin et al., 2005). The title bromo analog (Scheme I) is not, however, isomorphous as it crystallizes as a water-coordinated, dinuclear compound (Fig. 1). One nicotinate ion functions in an O,O'-chelating mode whereas the other nicotinate ion functions in an O:N'-bridging mode. The two seven-coordinate tin atoms show trans-C2SnNO4 pentagonal bipyramidal geometry; the C2Sn skeletons are nearly linear (Table 1).

Related literature top

For the crystal structure of [Sn(C7H6F)2(C6H4NO2)]2, see: Yin et al. (2005).

Experimental top

Di(4-bromobenzyl)tin oxide (0.40 g, 0.84 mmol) was suspended in chloroform (20 ml) and to the suspension was added an ethanol (20 ml) solution of nicotinic acid (0.21 g, 1.68 mmol). The mixture was heated for three hours; the solution was filtere and the solvent allow to evaporate. Colorless crystals were isolated after several days.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.99, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,O). The final difference Fourier map had a peak of 1.7 e Å-3 at 0.83 Å from Br3 and a hole of -1.4 e Å-3 at 0.7 Å from Br3.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot of [Sn(H2O)(C7H6Br)2(C6H4NO2)]2; ellipsoids are drawn at the 70% probability level and H atoms are of arbitrary radius.
Di-µ-nicotinato-κ2N:O;κ2O:N- bis[aquabis(4-bromobenzyl)(nicotinato-κ2O,O')tin(IV)] top
Crystal data top
[Sn2(C7H6Br)4(C6H4NO2)4(H2O)2]F(000) = 5632
Mr = 1441.93Dx = 1.868 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9852 reflections
a = 28.3754 (13) Åθ = 2.4–28.3°
b = 16.7568 (7) ŵ = 4.16 mm1
c = 21.5642 (10) ÅT = 100 K
β = 90.998 (1)°Block, colourless
V = 10251.8 (8) Å30.45 × 0.15 × 0.15 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
11790 independent reflections
Radiation source: fine-focus sealed tube9879 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3636
Tmin = 0.256, Tmax = 0.575k = 2121
48701 measured reflectionsl = 2828
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0282P)2]
where P = (Fo2 + 2Fc2)/3
11790 reflections(Δ/σ)max = 0.001
649 parametersΔρmax = 1.71 e Å3
0 restraintsΔρmin = 1.35 e Å3
Crystal data top
[Sn2(C7H6Br)4(C6H4NO2)4(H2O)2]V = 10251.8 (8) Å3
Mr = 1441.93Z = 8
Monoclinic, C2/cMo Kα radiation
a = 28.3754 (13) ŵ = 4.16 mm1
b = 16.7568 (7) ÅT = 100 K
c = 21.5642 (10) Å0.45 × 0.15 × 0.15 mm
β = 90.998 (1)°
Data collection top
Bruker SMART APEX
diffractometer
11790 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
9879 reflections with I > 2σ(I)
Tmin = 0.256, Tmax = 0.575Rint = 0.040
48701 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.18Δρmax = 1.71 e Å3
11790 reflectionsΔρmin = 1.35 e Å3
649 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.127365 (6)0.398907 (10)0.475980 (8)0.01245 (5)
Sn20.118973 (6)0.852588 (10)0.497094 (8)0.01254 (5)
Br10.061186 (11)0.031350 (17)0.317354 (15)0.02867 (8)
Br20.184067 (10)0.707467 (17)0.714509 (13)0.02448 (7)
Br30.189153 (11)1.149300 (19)0.736615 (16)0.03382 (8)
Br40.068462 (11)0.57137 (2)0.243172 (15)0.03221 (8)
O10.18011 (6)0.33219 (10)0.41027 (8)0.0168 (4)
O20.14491 (6)0.26003 (10)0.48040 (8)0.0171 (4)
O30.09053 (6)0.50964 (10)0.50952 (8)0.0151 (4)
O40.04097 (7)0.47396 (10)0.58468 (10)0.0247 (5)
O50.07314 (6)0.91872 (10)0.57150 (9)0.0178 (4)
O60.10635 (6)0.99148 (10)0.50002 (8)0.0174 (4)
O70.15283 (6)0.74040 (10)0.45926 (8)0.0148 (4)
O80.19850 (6)0.77716 (10)0.37971 (9)0.0187 (4)
O1w0.08643 (7)0.34945 (11)0.55222 (10)0.0286 (5)
H1w10.08380.38400.58020.043*
H1w20.10030.30910.56670.043*
O2w0.15534 (6)0.90247 (10)0.41642 (8)0.0193 (4)
H2w10.14090.94320.40370.029*
H2w20.15590.86830.38800.029*
N10.18947 (8)0.04941 (12)0.39462 (10)0.0170 (5)
N20.08851 (7)0.74508 (12)0.56837 (10)0.0146 (4)
N30.07093 (8)1.20199 (12)0.59318 (10)0.0177 (5)
N40.15900 (7)0.50348 (12)0.40569 (10)0.0140 (4)
C10.07051 (9)0.38070 (15)0.41051 (13)0.0203 (6)
H1A0.04060.39570.43040.024*
H1B0.07490.41690.37480.024*
C20.06617 (9)0.29671 (15)0.38672 (13)0.0171 (5)
C30.04277 (9)0.23804 (16)0.41982 (13)0.0197 (6)
H30.02790.25220.45740.024*
C40.04046 (9)0.15967 (16)0.39964 (13)0.0192 (6)
H40.02430.12050.42300.023*
C50.06211 (9)0.13949 (15)0.34497 (13)0.0190 (6)
C60.08511 (10)0.19585 (16)0.31007 (12)0.0210 (6)
H60.09940.18140.27210.025*
C70.08709 (10)0.27414 (16)0.33135 (13)0.0202 (6)
H70.10310.31310.30760.024*
C80.18753 (9)0.41961 (15)0.53542 (12)0.0169 (5)
H8A0.19260.37130.56110.020*
H8B0.21550.42580.50900.020*
C90.18555 (9)0.49006 (15)0.57785 (12)0.0150 (5)
C100.20789 (9)0.56172 (15)0.56315 (12)0.0179 (6)
H100.22390.56610.52500.021*
C110.20727 (9)0.62685 (15)0.60305 (13)0.0174 (6)
H110.22260.67520.59240.021*
C120.18395 (9)0.61987 (15)0.65828 (12)0.0168 (5)
C130.16116 (9)0.55024 (16)0.67453 (12)0.0181 (6)
H130.14520.54650.71280.022*
C140.16198 (9)0.48563 (15)0.63386 (12)0.0167 (5)
H140.14620.43770.64450.020*
C150.17112 (8)0.26564 (14)0.43434 (12)0.0123 (5)
C160.19032 (9)0.19214 (14)0.40448 (11)0.0126 (5)
C170.22184 (9)0.19773 (15)0.35631 (12)0.0165 (5)
H170.23290.24830.34310.020*
C180.23693 (10)0.12886 (15)0.32781 (12)0.0187 (6)
H180.25870.13120.29490.022*
C190.21978 (9)0.05604 (15)0.34813 (12)0.0176 (6)
H190.23000.00880.32810.021*
C200.17523 (9)0.11638 (15)0.42222 (13)0.0162 (5)
H200.15380.11220.45550.019*
C210.06516 (9)0.52344 (15)0.55653 (12)0.0148 (5)
C220.06603 (8)0.60797 (14)0.58108 (12)0.0131 (5)
C230.04915 (9)0.62469 (15)0.64008 (12)0.0156 (5)
H230.03530.58400.66440.019*
C240.05306 (9)0.70185 (15)0.66245 (12)0.0182 (6)
H240.04220.71460.70270.022*
C250.07298 (9)0.76045 (15)0.62577 (12)0.0163 (5)
H250.07570.81310.64170.020*
C260.08499 (9)0.66972 (14)0.54711 (12)0.0148 (5)
H260.09610.65840.50670.018*
C270.18036 (9)0.86188 (15)0.55646 (13)0.0174 (6)
H27A0.18240.81280.58200.021*
H27B0.20850.86300.52990.021*
C280.18292 (9)0.93245 (15)0.59928 (12)0.0166 (5)
C290.16707 (9)0.92619 (16)0.66014 (13)0.0197 (6)
H290.15530.87650.67430.024*
C300.16818 (9)0.99067 (17)0.70021 (13)0.0212 (6)
H300.15680.98570.74120.025*
C310.18609 (9)1.06259 (16)0.67960 (13)0.0210 (6)
C320.20203 (10)1.07127 (16)0.61970 (14)0.0226 (6)
H320.21401.12100.60590.027*
C330.20016 (9)1.00592 (15)0.58009 (13)0.0190 (6)
H330.21091.01160.53880.023*
C340.05569 (9)0.83499 (15)0.44248 (13)0.0179 (6)
H34A0.02970.82200.47080.021*
H34B0.04760.88590.42160.021*
C350.05825 (9)0.77112 (15)0.39438 (12)0.0159 (5)
C360.03717 (9)0.69641 (15)0.40305 (12)0.0174 (5)
H360.02050.68660.44010.021*
C370.04008 (9)0.63636 (15)0.35879 (13)0.0175 (6)
H370.02540.58620.36510.021*
C380.06478 (9)0.65132 (16)0.30563 (13)0.0192 (6)
C390.08604 (9)0.72418 (16)0.29506 (12)0.0203 (6)
H390.10290.73330.25810.024*
C400.08231 (9)0.78390 (16)0.33935 (12)0.0187 (6)
H400.09640.83440.33210.022*
C410.08379 (9)0.98551 (14)0.54961 (12)0.0132 (5)
C420.07266 (9)1.05913 (14)0.58653 (12)0.0135 (5)
C430.05598 (9)1.05319 (15)0.64635 (12)0.0178 (6)
H430.05081.00240.66460.021*
C440.04701 (10)1.12212 (16)0.67904 (13)0.0202 (6)
H440.03591.11970.72030.024*
C450.05458 (9)1.19507 (15)0.65050 (12)0.0182 (6)
H450.04781.24240.67290.022*
C460.08032 (9)1.13463 (14)0.56181 (12)0.0162 (5)
H460.09261.13880.52130.019*
C470.17733 (8)0.72694 (14)0.41137 (11)0.0125 (5)
C480.17991 (8)0.64110 (14)0.39044 (12)0.0120 (5)
C490.20248 (9)0.62168 (15)0.33556 (12)0.0165 (5)
H490.21770.66160.31190.020*
C500.20213 (9)0.54268 (15)0.31627 (12)0.0181 (6)
H500.21710.52780.27900.022*
C510.17979 (9)0.48584 (15)0.35180 (12)0.0161 (5)
H510.17910.43220.33760.019*
C520.15920 (9)0.58055 (14)0.42374 (12)0.0136 (5)
H520.14430.59390.46140.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01387 (9)0.00750 (8)0.01606 (9)0.00060 (6)0.00270 (7)0.00051 (6)
Sn20.01477 (9)0.00796 (8)0.01494 (9)0.00121 (6)0.00193 (7)0.00129 (6)
Br10.03283 (17)0.01812 (14)0.03515 (18)0.00559 (12)0.00369 (14)0.00993 (12)
Br20.02351 (15)0.02344 (15)0.02635 (16)0.00356 (11)0.00397 (12)0.01179 (12)
Br30.02835 (17)0.03383 (17)0.03937 (19)0.00471 (13)0.00374 (14)0.02383 (14)
Br40.02297 (16)0.04017 (18)0.03365 (18)0.00338 (13)0.00543 (13)0.02233 (14)
O10.0216 (10)0.0087 (8)0.0202 (10)0.0004 (7)0.0031 (8)0.0001 (7)
O20.0173 (9)0.0133 (9)0.0207 (10)0.0005 (7)0.0049 (8)0.0019 (7)
O30.0169 (9)0.0104 (8)0.0180 (10)0.0006 (7)0.0054 (7)0.0010 (7)
O40.0260 (11)0.0105 (9)0.0381 (12)0.0027 (8)0.0181 (9)0.0006 (8)
O50.0205 (10)0.0099 (9)0.0230 (10)0.0013 (7)0.0034 (8)0.0003 (7)
O60.0212 (10)0.0126 (9)0.0186 (10)0.0014 (7)0.0032 (8)0.0014 (7)
O70.0186 (9)0.0098 (8)0.0163 (9)0.0012 (7)0.0034 (7)0.0003 (7)
O80.0217 (10)0.0099 (9)0.0249 (10)0.0037 (7)0.0083 (8)0.0006 (7)
O1w0.0395 (13)0.0098 (9)0.0374 (13)0.0066 (8)0.0227 (10)0.0025 (8)
O2w0.0272 (11)0.0101 (9)0.0208 (10)0.0014 (8)0.0073 (8)0.0015 (7)
N10.0183 (12)0.0110 (10)0.0218 (12)0.0016 (9)0.0020 (9)0.0003 (9)
N20.0155 (11)0.0094 (10)0.0190 (12)0.0004 (8)0.0004 (9)0.0005 (8)
N30.0205 (12)0.0118 (11)0.0210 (12)0.0010 (9)0.0026 (9)0.0000 (9)
N40.0163 (11)0.0097 (10)0.0161 (11)0.0002 (8)0.0013 (9)0.0007 (8)
C10.0174 (14)0.0140 (13)0.0294 (16)0.0026 (10)0.0043 (12)0.0010 (11)
C20.0129 (13)0.0153 (13)0.0228 (14)0.0016 (10)0.0045 (11)0.0009 (11)
C30.0186 (14)0.0198 (14)0.0210 (14)0.0030 (11)0.0033 (11)0.0037 (11)
C40.0173 (14)0.0173 (13)0.0231 (15)0.0058 (11)0.0015 (11)0.0007 (11)
C50.0203 (14)0.0142 (13)0.0224 (15)0.0040 (11)0.0052 (12)0.0063 (11)
C60.0240 (15)0.0246 (15)0.0143 (13)0.0030 (12)0.0000 (11)0.0041 (11)
C70.0227 (15)0.0180 (13)0.0198 (14)0.0063 (11)0.0011 (11)0.0041 (11)
C80.0174 (13)0.0138 (12)0.0194 (14)0.0012 (10)0.0008 (11)0.0022 (10)
C90.0124 (13)0.0160 (13)0.0164 (13)0.0018 (10)0.0032 (10)0.0007 (10)
C100.0161 (13)0.0214 (14)0.0162 (13)0.0015 (11)0.0005 (11)0.0004 (11)
C110.0135 (13)0.0146 (13)0.0241 (15)0.0001 (10)0.0007 (11)0.0019 (11)
C120.0144 (13)0.0177 (13)0.0180 (14)0.0044 (10)0.0049 (11)0.0063 (10)
C130.0162 (13)0.0227 (14)0.0153 (13)0.0033 (11)0.0010 (11)0.0005 (11)
C140.0140 (13)0.0163 (13)0.0198 (14)0.0006 (10)0.0008 (11)0.0011 (11)
C150.0096 (12)0.0091 (11)0.0182 (13)0.0004 (9)0.0026 (10)0.0010 (10)
C160.0140 (12)0.0098 (12)0.0138 (12)0.0013 (9)0.0011 (10)0.0007 (10)
C170.0188 (14)0.0123 (12)0.0182 (13)0.0011 (10)0.0000 (11)0.0028 (10)
C180.0221 (14)0.0196 (14)0.0144 (13)0.0018 (11)0.0050 (11)0.0017 (10)
C190.0225 (14)0.0138 (13)0.0165 (13)0.0043 (11)0.0029 (11)0.0023 (10)
C200.0159 (13)0.0119 (12)0.0210 (14)0.0001 (10)0.0036 (11)0.0000 (10)
C210.0130 (12)0.0115 (12)0.0198 (14)0.0019 (10)0.0002 (10)0.0004 (10)
C220.0112 (12)0.0106 (12)0.0174 (13)0.0030 (9)0.0015 (10)0.0008 (10)
C230.0155 (13)0.0141 (12)0.0170 (13)0.0015 (10)0.0022 (11)0.0038 (10)
C240.0209 (14)0.0205 (14)0.0131 (13)0.0014 (11)0.0014 (11)0.0014 (10)
C250.0203 (14)0.0127 (12)0.0160 (13)0.0009 (10)0.0008 (11)0.0007 (10)
C260.0136 (12)0.0133 (12)0.0177 (13)0.0018 (10)0.0022 (10)0.0002 (10)
C270.0174 (13)0.0131 (12)0.0218 (14)0.0009 (10)0.0002 (11)0.0033 (10)
C280.0133 (13)0.0163 (13)0.0201 (14)0.0001 (10)0.0020 (11)0.0031 (11)
C290.0188 (14)0.0190 (13)0.0214 (14)0.0017 (11)0.0008 (11)0.0019 (11)
C300.0187 (14)0.0290 (15)0.0160 (14)0.0010 (12)0.0017 (11)0.0036 (11)
C310.0167 (14)0.0225 (14)0.0238 (15)0.0009 (11)0.0024 (11)0.0114 (12)
C320.0213 (15)0.0162 (13)0.0301 (16)0.0044 (11)0.0004 (12)0.0049 (12)
C330.0196 (14)0.0188 (13)0.0188 (14)0.0026 (11)0.0031 (11)0.0042 (11)
C340.0175 (14)0.0140 (13)0.0222 (14)0.0000 (10)0.0004 (11)0.0009 (11)
C350.0122 (12)0.0168 (13)0.0186 (13)0.0004 (10)0.0020 (10)0.0018 (10)
C360.0150 (13)0.0200 (13)0.0171 (13)0.0016 (10)0.0016 (10)0.0005 (11)
C370.0134 (13)0.0163 (13)0.0229 (15)0.0020 (10)0.0008 (11)0.0013 (11)
C380.0163 (13)0.0225 (14)0.0187 (14)0.0017 (11)0.0031 (11)0.0081 (11)
C390.0174 (14)0.0301 (15)0.0132 (13)0.0045 (12)0.0005 (11)0.0018 (11)
C400.0188 (14)0.0187 (13)0.0185 (14)0.0029 (11)0.0026 (11)0.0036 (11)
C410.0119 (12)0.0087 (11)0.0190 (13)0.0029 (9)0.0019 (10)0.0026 (10)
C420.0125 (12)0.0115 (12)0.0166 (13)0.0009 (10)0.0005 (10)0.0003 (10)
C430.0199 (14)0.0139 (12)0.0198 (14)0.0014 (10)0.0034 (11)0.0039 (10)
C440.0229 (15)0.0214 (14)0.0163 (14)0.0023 (11)0.0044 (11)0.0002 (11)
C450.0205 (14)0.0142 (13)0.0200 (14)0.0038 (10)0.0009 (11)0.0044 (11)
C460.0179 (13)0.0140 (13)0.0169 (14)0.0000 (10)0.0041 (11)0.0007 (10)
C470.0119 (12)0.0105 (12)0.0151 (13)0.0008 (9)0.0021 (10)0.0001 (10)
C480.0115 (12)0.0098 (12)0.0148 (13)0.0009 (9)0.0012 (10)0.0001 (9)
C490.0172 (13)0.0133 (12)0.0190 (14)0.0013 (10)0.0010 (11)0.0023 (10)
C500.0247 (15)0.0155 (13)0.0143 (13)0.0010 (11)0.0050 (11)0.0008 (10)
C510.0205 (14)0.0120 (12)0.0158 (13)0.0016 (10)0.0003 (11)0.0026 (10)
C520.0127 (12)0.0111 (12)0.0171 (13)0.0005 (9)0.0017 (10)0.0006 (10)
Geometric parameters (Å, º) top
Sn1—C82.145 (3)C14—H140.9500
Sn1—C12.147 (3)C15—C161.497 (3)
Sn1—O1w2.1922 (18)C16—C171.386 (3)
Sn1—O32.2549 (17)C16—C201.395 (3)
Sn1—O12.3605 (17)C17—C181.379 (4)
Sn1—O22.3813 (17)C17—H170.9500
Sn1—N42.494 (2)C18—C191.387 (4)
Sn2—C272.149 (3)C18—H180.9500
Sn2—C342.150 (3)C19—H190.9500
Sn2—O2w2.2029 (17)C20—H200.9500
Sn2—O72.2695 (16)C21—C221.512 (3)
Sn2—O62.3558 (17)C22—C261.382 (3)
Sn2—O52.3594 (17)C22—C231.396 (3)
Sn2—N22.530 (2)C23—C241.384 (4)
Br1—C51.907 (3)C23—H230.9500
Br2—C121.904 (3)C24—C251.387 (3)
Br3—C311.904 (3)C24—H240.9500
Br4—C381.904 (3)C25—H250.9500
O1—C151.258 (3)C26—H260.9500
O2—C151.255 (3)C27—C281.501 (3)
O3—C211.275 (3)C27—H27A0.9900
O4—C211.242 (3)C27—H27B0.9900
O5—C411.254 (3)C28—C331.390 (4)
O6—C411.260 (3)C28—C291.399 (4)
O7—C471.275 (3)C29—C301.383 (4)
O8—C471.245 (3)C29—H290.9500
O1w—H1w10.8400C30—C311.384 (4)
O1w—H1w20.8400C30—H300.9500
O2w—H2w10.8400C31—C321.384 (4)
O2w—H2w20.8400C32—C331.389 (4)
N1—C201.336 (3)C32—H320.9500
N1—C191.337 (3)C33—H330.9500
N2—C261.347 (3)C34—C351.493 (3)
N2—C251.346 (3)C34—H34A0.9900
N3—C451.333 (3)C34—H34B0.9900
N3—C461.345 (3)C35—C401.396 (4)
N4—C511.345 (3)C35—C361.401 (4)
N4—C521.349 (3)C36—C371.390 (4)
C1—C21.502 (4)C36—H360.9500
C1—H1A0.9900C37—C381.377 (4)
C1—H1B0.9900C37—H370.9500
C2—C31.390 (4)C38—C391.382 (4)
C2—C71.395 (4)C39—C401.389 (4)
C3—C41.385 (4)C39—H390.9500
C3—H30.9500C40—H400.9500
C4—C51.381 (4)C41—C421.505 (3)
C4—H40.9500C42—C431.385 (3)
C5—C61.379 (4)C42—C461.391 (3)
C6—C71.391 (4)C43—C441.379 (4)
C6—H60.9500C43—H430.9500
C7—H70.9500C44—C451.387 (4)
C8—C91.495 (3)C44—H440.9500
C8—H8A0.9900C45—H450.9500
C8—H8B0.9900C46—H460.9500
C9—C141.393 (3)C47—C481.510 (3)
C9—C101.397 (4)C48—C521.380 (3)
C10—C111.390 (4)C48—C491.394 (3)
C10—H100.9500C49—C501.387 (3)
C11—C121.377 (4)C49—H490.9500
C11—H110.9500C50—C511.383 (3)
C12—C131.382 (4)C50—H500.9500
C13—C141.394 (4)C51—H510.9500
C13—H130.9500C52—H520.9500
C1—Sn1—C8175.5 (1)C20—C16—C15121.0 (2)
C8—Sn1—O1w92.27 (9)C18—C17—C16119.1 (2)
C1—Sn1—O1w92.15 (10)C18—C17—H17120.4
C8—Sn1—O392.50 (8)C16—C17—H17120.4
C1—Sn1—O388.89 (8)C17—C18—C19118.8 (2)
O1w—Sn1—O379.39 (6)C17—C18—H18120.6
C8—Sn1—O185.93 (8)C19—C18—H18120.6
C1—Sn1—O190.86 (9)N1—C19—C18122.9 (2)
O1w—Sn1—O1128.39 (6)N1—C19—H19118.5
O3—Sn1—O1152.19 (6)C18—C19—H19118.5
C8—Sn1—O288.31 (8)N1—C20—C16123.1 (2)
C1—Sn1—O292.39 (8)N1—C20—H20118.5
O1w—Sn1—O273.36 (6)C16—C20—H20118.5
O3—Sn1—O2152.75 (6)O4—C21—O3126.3 (2)
O1—Sn1—O255.04 (6)O4—C21—C22117.4 (2)
C8—Sn1—N487.61 (9)O3—C21—C22116.2 (2)
C1—Sn1—N488.54 (9)C26—C22—C23118.4 (2)
O1w—Sn1—N4157.27 (7)C26—C22—C21121.3 (2)
O3—Sn1—N477.91 (6)C23—C22—C21120.2 (2)
O1—Sn1—N474.29 (6)C24—C23—C22118.6 (2)
O2—Sn1—N4129.32 (6)C24—C23—H23120.7
C27—Sn2—C34175.2 (1)C22—C23—H23120.7
C27—Sn2—O2w93.27 (9)C23—C24—C25119.6 (2)
C34—Sn2—O2w91.01 (9)C23—C24—H24120.2
C27—Sn2—O786.01 (8)C25—C24—H24120.2
C34—Sn2—O792.53 (8)N2—C25—C24122.1 (2)
O2w—Sn2—O779.82 (6)N2—C25—H25118.9
C27—Sn2—O691.98 (8)C24—C25—H25118.9
C34—Sn2—O691.39 (8)N2—C26—C22123.3 (2)
O2w—Sn2—O673.73 (6)N2—C26—H26118.4
O7—Sn2—O6153.32 (6)C22—C26—H26118.4
C27—Sn2—O590.66 (8)C28—C27—Sn2116.96 (18)
C34—Sn2—O588.39 (8)C28—C27—H27A108.1
O2w—Sn2—O5129.06 (6)Sn2—C27—H27A108.1
O7—Sn2—O5151.09 (6)C28—C27—H27B108.1
O6—Sn2—O555.38 (6)Sn2—C27—H27B108.1
C27—Sn2—N288.38 (9)H27A—C27—H27B107.3
C34—Sn2—N286.80 (9)C33—C28—C29117.8 (2)
O2w—Sn2—N2156.88 (6)C33—C28—C27121.9 (2)
O7—Sn2—N277.28 (6)C29—C28—C27120.3 (2)
O6—Sn2—N2129.30 (6)C30—C29—C28121.6 (2)
O5—Sn2—N273.92 (6)C30—C29—H29119.2
C15—O1—Sn192.11 (14)C28—C29—H29119.2
C15—O2—Sn191.23 (14)C29—C30—C31118.9 (3)
C21—O3—Sn1132.51 (16)C29—C30—H30120.5
C41—O5—Sn291.36 (14)C31—C30—H30120.5
C41—O6—Sn291.37 (14)C32—C31—C30121.3 (2)
C47—O7—Sn2132.68 (15)C32—C31—Br3120.7 (2)
Sn1—O1w—H1w1109.5C30—C31—Br3118.0 (2)
Sn1—O1w—H1w2109.5C31—C32—C33118.8 (3)
H1w1—O1w—H1w2109.5C31—C32—H32120.6
Sn2—O2w—H2w1109.5C33—C32—H32120.6
Sn2—O2w—H2w2109.5C32—C33—C28121.6 (3)
H2w1—O2w—H2w2109.5C32—C33—H33119.2
C20—N1—C19117.9 (2)C28—C33—H33119.2
C26—N2—C25118.0 (2)C35—C34—Sn2115.37 (17)
C26—N2—Sn2119.01 (16)C35—C34—H34A108.4
C25—N2—Sn2122.91 (16)Sn2—C34—H34A108.4
C45—N3—C46117.9 (2)C35—C34—H34B108.4
C51—N4—C52117.4 (2)Sn2—C34—H34B108.4
C51—N4—Sn1122.58 (16)H34A—C34—H34B107.5
C52—N4—Sn1119.81 (16)C40—C35—C36117.8 (2)
C2—C1—Sn1114.44 (18)C40—C35—C34120.7 (2)
C2—C1—H1A108.7C36—C35—C34121.4 (2)
Sn1—C1—H1A108.7C37—C36—C35121.6 (2)
C2—C1—H1B108.7C37—C36—H36119.2
Sn1—C1—H1B108.7C35—C36—H36119.2
H1A—C1—H1B107.6C38—C37—C36118.5 (2)
C3—C2—C7117.5 (2)C38—C37—H37120.8
C3—C2—C1121.6 (2)C36—C37—H37120.8
C7—C2—C1120.8 (2)C37—C38—C39121.9 (2)
C4—C3—C2122.0 (2)C37—C38—Br4119.7 (2)
C4—C3—H3119.0C39—C38—Br4118.4 (2)
C2—C3—H3119.0C38—C39—C40119.0 (2)
C5—C4—C3118.8 (2)C38—C39—H39120.5
C5—C4—H4120.6C40—C39—H39120.5
C3—C4—H4120.6C39—C40—C35121.2 (2)
C6—C5—C4121.3 (2)C39—C40—H40119.4
C6—C5—Br1119.0 (2)C35—C40—H40119.4
C4—C5—Br1119.7 (2)O5—C41—O6121.3 (2)
C5—C6—C7118.9 (2)O5—C41—C42118.6 (2)
C5—C6—H6120.6O6—C41—C42119.9 (2)
C7—C6—H6120.6C43—C42—C46118.7 (2)
C6—C7—C2121.5 (2)C43—C42—C41120.8 (2)
C6—C7—H7119.2C46—C42—C41120.5 (2)
C2—C7—H7119.2C44—C43—C42119.0 (2)
C9—C8—Sn1117.10 (17)C44—C43—H43120.5
C9—C8—H8A108.0C42—C43—H43120.5
Sn1—C8—H8A108.0C43—C44—C45118.7 (2)
C9—C8—H8B108.0C43—C44—H44120.7
Sn1—C8—H8B108.0C45—C44—H44120.7
H8A—C8—H8B107.3N3—C45—C44123.2 (2)
C14—C9—C10118.0 (2)N3—C45—H45118.4
C14—C9—C8120.8 (2)C44—C45—H45118.4
C10—C9—C8121.2 (2)N3—C46—C42122.5 (2)
C11—C10—C9121.6 (2)N3—C46—H46118.8
C11—C10—H10119.2C42—C46—H46118.8
C9—C10—H10119.2O8—C47—O7126.9 (2)
C12—C11—C10118.7 (2)O8—C47—C48117.0 (2)
C12—C11—H11120.7O7—C47—C48116.1 (2)
C10—C11—H11120.7C52—C48—C49118.4 (2)
C11—C12—C13121.7 (2)C52—C48—C47121.4 (2)
C11—C12—Br2119.3 (2)C49—C48—C47120.1 (2)
C13—C12—Br2119.0 (2)C50—C49—C48118.4 (2)
C12—C13—C14118.9 (2)C50—C49—H49120.8
C12—C13—H13120.5C48—C49—H49120.8
C14—C13—H13120.5C51—C50—C49119.5 (2)
C9—C14—C13121.2 (2)C51—C50—H50120.3
C9—C14—H14119.4C49—C50—H50120.3
C13—C14—H14119.4N4—C51—C50122.6 (2)
O2—C15—O1121.4 (2)N4—C51—H51118.7
O2—C15—C16120.3 (2)C50—C51—H51118.7
O1—C15—C16118.3 (2)N4—C52—C48123.6 (2)
C17—C16—C20118.2 (2)N4—C52—H52118.2
C17—C16—C15120.8 (2)C48—C52—H52118.2
C8—Sn1—O1—C1593.71 (16)Sn1—O1—C15—O25.3 (3)
C1—Sn1—O1—C1589.39 (16)Sn1—O1—C15—C16171.3 (2)
O1w—Sn1—O1—C154.04 (19)O2—C15—C16—C17175.6 (2)
O3—Sn1—O1—C15178.64 (15)O1—C15—C16—C177.8 (4)
O2—Sn1—O1—C152.92 (14)O2—C15—C16—C207.7 (4)
N4—Sn1—O1—C15177.63 (16)O1—C15—C16—C20169.0 (2)
C8—Sn1—O2—C1589.15 (16)C20—C16—C17—C180.1 (4)
C1—Sn1—O2—C1586.45 (16)C15—C16—C17—C18176.7 (2)
O1w—Sn1—O2—C15177.98 (16)C16—C17—C18—C190.4 (4)
O3—Sn1—O2—C15178.66 (15)C20—N1—C19—C180.2 (4)
O1—Sn1—O2—C152.93 (14)C17—C18—C19—N10.6 (4)
N4—Sn1—O2—C153.62 (18)C19—N1—C20—C160.4 (4)
C8—Sn1—O3—C2183.8 (2)C17—C16—C20—N10.5 (4)
C1—Sn1—O3—C21100.4 (2)C15—C16—C20—N1176.3 (2)
O1w—Sn1—O3—C218.0 (2)Sn1—O3—C21—O426.9 (4)
O1—Sn1—O3—C21169.8 (2)Sn1—O3—C21—C22151.20 (17)
O2—Sn1—O3—C217.4 (3)O4—C21—C22—C26168.6 (2)
N4—Sn1—O3—C21170.8 (2)O3—C21—C22—C2613.2 (4)
C27—Sn2—O5—C4187.77 (16)O4—C21—C22—C2313.9 (4)
C34—Sn2—O5—C4196.97 (16)O3—C21—C22—C23164.4 (2)
O2w—Sn2—O5—C416.97 (19)C26—C22—C23—C241.4 (4)
O7—Sn2—O5—C41170.69 (15)C21—C22—C23—C24176.2 (2)
O6—Sn2—O5—C414.17 (14)C22—C23—C24—C250.8 (4)
N2—Sn2—O5—C41175.89 (17)C26—N2—C25—C241.1 (4)
C27—Sn2—O6—C4185.29 (16)Sn2—N2—C25—C24174.98 (19)
C34—Sn2—O6—C4191.24 (16)C23—C24—C25—N20.5 (4)
O2w—Sn2—O6—C41178.12 (16)C25—N2—C26—C220.4 (4)
O7—Sn2—O6—C41170.32 (15)Sn2—N2—C26—C22175.80 (19)
O5—Sn2—O6—C414.15 (14)C23—C22—C26—N20.8 (4)
N2—Sn2—O6—C414.23 (18)C21—C22—C26—N2176.8 (2)
C27—Sn2—O7—C4797.4 (2)O2w—Sn2—C27—C2899.23 (19)
C34—Sn2—O7—C4787.2 (2)O7—Sn2—C27—C28178.8 (2)
O2w—Sn2—O7—C473.4 (2)O6—Sn2—C27—C2825.4 (2)
O6—Sn2—O7—C4711.0 (3)O5—Sn2—C27—C2829.96 (19)
O5—Sn2—O7—C47178.46 (19)N2—Sn2—C27—C28103.9 (2)
N2—Sn2—O7—C47173.3 (2)Sn2—C27—C28—C3384.9 (3)
C27—Sn2—N2—C26112.81 (19)Sn2—C27—C28—C2994.0 (3)
C34—Sn2—N2—C2666.78 (19)C33—C28—C29—C300.2 (4)
O2w—Sn2—N2—C2618.3 (3)C27—C28—C29—C30178.8 (3)
O7—Sn2—N2—C2626.54 (18)C28—C29—C30—C311.0 (4)
O6—Sn2—N2—C26155.96 (17)C29—C30—C31—C321.1 (4)
O5—Sn2—N2—C26156.0 (2)C29—C30—C31—Br3177.9 (2)
C27—Sn2—N2—C2571.1 (2)C30—C31—C32—C330.5 (4)
C34—Sn2—N2—C25109.3 (2)Br3—C31—C32—C33178.5 (2)
O2w—Sn2—N2—C25165.67 (19)C31—C32—C33—C280.3 (4)
O7—Sn2—N2—C25157.4 (2)C29—C28—C33—C320.4 (4)
O6—Sn2—N2—C2520.1 (2)C27—C28—C33—C32179.4 (3)
O5—Sn2—N2—C2520.01 (19)fO2w—Sn2—C34—C3569.71 (19)
C8—Sn1—N4—C51105.0 (2)O7—Sn2—C34—C3510.15 (19)
C1—Sn1—N4—C5172.7 (2)O6—Sn2—C34—C35143.46 (19)
O1w—Sn1—N4—C51164.8 (2)O5—Sn2—C34—C35161.24 (19)
O3—Sn1—N4—C51161.9 (2)N2—Sn2—C34—C3587.25 (19)
O1—Sn1—N4—C5118.55 (19)Sn2—C34—C35—C4075.8 (3)
O2—Sn1—N4—C5119.1 (2)Sn2—C34—C35—C36103.5 (3)
C8—Sn1—N4—C5269.34 (19)C40—C35—C36—C370.3 (4)
C1—Sn1—N4—C52112.9 (2)C34—C35—C36—C37179.0 (2)
O1w—Sn1—N4—C5220.8 (3)C35—C36—C37—C380.6 (4)
O3—Sn1—N4—C5223.74 (18)C36—C37—C38—C390.8 (4)
O1—Sn1—N4—C52155.8 (2)C36—C37—C38—Br4178.7 (2)
O2—Sn1—N4—C52155.19 (17)C37—C38—C39—C400.0 (4)
O1w—Sn1—C1—C280.2 (2)Br4—C38—C39—C40177.9 (2)
O3—Sn1—C1—C2159.5 (2)C38—C39—C40—C351.0 (4)
O1—Sn1—C1—C248.3 (2)C36—C35—C40—C391.2 (4)
O2—Sn1—C1—C26.8 (2)C34—C35—C40—C39178.2 (2)
N4—Sn1—C1—C2122.5 (2)Sn2—O5—C41—O67.5 (3)
Sn1—C1—C2—C383.1 (3)Sn2—O5—C41—C42167.4 (2)
Sn1—C1—C2—C794.6 (3)Sn2—O6—C41—O57.5 (3)
C7—C2—C3—C40.8 (4)Sn2—O6—C41—C42167.3 (2)
C1—C2—C3—C4177.0 (3)O5—C41—C42—C437.2 (4)
C2—C3—C4—C50.0 (4)O6—C41—C42—C43167.8 (2)
C3—C4—C5—C61.0 (4)O5—C41—C42—C46174.7 (2)
C3—C4—C5—Br1178.1 (2)O6—C41—C42—C4610.3 (4)
C4—C5—C6—C71.2 (4)C46—C42—C43—C440.8 (4)
Br1—C5—C6—C7177.9 (2)C41—C42—C43—C44178.8 (2)
C5—C6—C7—C20.4 (4)C42—C43—C44—C450.7 (4)
C3—C2—C7—C60.6 (4)C46—N3—C45—C440.2 (4)
C1—C2—C7—C6177.2 (3)C43—C44—C45—N31.2 (4)
O1w—Sn1—C8—C976.71 (19)C45—N3—C46—C421.4 (4)
O3—Sn1—C8—C92.77 (19)C43—C42—C46—N31.8 (4)
O1—Sn1—C8—C9154.96 (19)C41—C42—C46—N3179.9 (2)
O2—Sn1—C8—C9149.98 (19)Sn2—O7—C47—O818.4 (4)
N4—Sn1—C8—C980.54 (19)Sn2—O7—C47—C48160.24 (16)
Sn1—C8—C9—C1481.5 (3)O8—C47—C48—C52177.4 (2)
Sn1—C8—C9—C1099.6 (3)O7—C47—C48—C523.8 (4)
C14—C9—C10—C110.6 (4)O8—C47—C48—C494.3 (4)
C8—C9—C10—C11178.3 (2)O7—C47—C48—C49174.5 (2)
C9—C10—C11—C120.0 (4)C52—C48—C49—C501.5 (4)
C10—C11—C12—C130.3 (4)C47—C48—C49—C50176.9 (2)
C10—C11—C12—Br2178.4 (2)C48—C49—C50—C510.3 (4)
C11—C12—C13—C140.1 (4)C52—N4—C51—C502.1 (4)
Br2—C12—C13—C14178.66 (19)Sn1—N4—C51—C50172.4 (2)
C10—C9—C14—C130.9 (4)C49—C50—C51—N41.6 (4)
C8—C9—C14—C13178.1 (2)C51—N4—C52—C480.8 (4)
C12—C13—C14—C90.5 (4)Sn1—N4—C52—C48173.81 (19)
Sn1—O2—C15—O15.3 (3)C49—C48—C52—N41.0 (4)
Sn1—O2—C15—C16171.3 (2)C47—C48—C52—N4177.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O40.841.942.557 (2)129
O1w—H1w2···N3i0.842.062.663 (3)128
O2w—H2w2···O80.841.962.563 (2)128
O2w—H2w1···N1ii0.842.262.690 (3)112
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Sn2(C7H6Br)4(C6H4NO2)4(H2O)2]
Mr1441.93
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)28.3754 (13), 16.7568 (7), 21.5642 (10)
β (°) 90.998 (1)
V3)10251.8 (8)
Z8
Radiation typeMo Kα
µ (mm1)4.16
Crystal size (mm)0.45 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.256, 0.575
No. of measured, independent and
observed [I > 2σ(I)] reflections
48701, 11790, 9879
Rint0.040
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.066, 1.18
No. of reflections11790
No. of parameters649
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.71, 1.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond angles (º) top
C1—Sn1—C8175.5 (1)C27—Sn2—C34175.2 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O40.841.942.557 (2)129
O1w—H1w2···N3i0.842.062.663 (3)128
O2w—H2w2···O80.841.962.563 (2)128
O2w—H2w1···N1ii0.842.262.690 (3)112
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals
First citationYin, H.-D., Wang, Q.-B. & Xue, S.-C. (2005). Indian J. Chem. Sect. B, 44, 2550–2554.

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