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

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ISSN: 2056-9890

Poly[piperazinediium [[aqua­bis­muth­ate(III)]-di-μ-pyridine-2,6-di­carboxyl­ato-bis­­muthate(III)-di-μ-pyridine-2,6-di­carboxyl­ato] monohydrate]

aFaculty of Chemistry, Teacher Training University, 49 Mofateh Avenue, 15614 Tehran, Iran, and bDepartment of Chemistry, University of Kurdistan, Sanandaj, Iran
*Correspondence e-mail: haghabozorg@yahoo.com

(Received 5 November 2007; accepted 15 January 2008; online 23 January 2008)

The title compound, {(C4H12N2)[Bi2(C7H3NO4)4(H2O)]·H2O}n or {(pipzH2)[Bi2(pydc)4(H2O)]·H2O}n, where pydcH2 is pyridine-2,6-dicarboxylic acid and pipz is piperazine, was obtained by reaction of Bi(NO3)3·5H2O with (pipzH2)(pydc­H)2·3H2O in a 1:2 molar ratio in aqueous solution. There are two independent BiIII atoms in the structure, one of which is eight-coordinate with a distorted bicapped trigonal-prismatic geometry, and another which is nine-coordinate with a distorted tricapped trigonal-prismatic geometry. The carboxyl­ate groups of the (pydc)2− ligands link dinuclear [Bi2(C7H3NO4)4(H2O)]2− units into one-dimensional coordin­ation polymers. The pipzH22+ cations (site symmetry [\overline{1}]) and non-coordinated water mol­ecules lie between these polymers, forming N—H⋯O and O—H⋯O hydrogen bonds to the O atoms of the carboxylate groups.

Related literature

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007[Aghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007). Acta Cryst. E63, m1803-m1804.]); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007[Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007). Acta Cryst. E63, m1710-m1711.]); Aghabozorg, Motyeian et al. (2007[Aghabozorg, H., Motyeian, E., Aghajani, Z., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m1754-m1755.]); Aghabozorg, Daneshvar et al. (2007[Aghabozorg, H., Daneshvar, S., Motyeian, E., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m2468-m2469.]); Sharif et al. (2007[Sharif, M. A., Aghabozorg, H. & Moghimi, A. (2007). Acta Cryst. E63, m1599-m1601.]); Sheshmani et al. (2006[Sheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620-o3622.]).

[Scheme 1]

Experimental

Crystal data
  • (C4H12N2)[Bi2(C7H3NO4)4(H2O)]·H2O

  • Mr = 1202.56

  • Triclinic, [P \overline 1]

  • a = 10.8111 (4) Å

  • b = 12.1660 (5) Å

  • c = 14.0402 (5) Å

  • α = 96.094 (1)°

  • β = 93.169 (1)°

  • γ = 113.848 (1)°

  • V = 1669.65 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 10.62 mm−1

  • T = 100 (2) K

  • 0.15 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.204, Tmax = 0.346

  • 22723 measured reflections

  • 8005 independent reflections

  • 6952 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.022

  • wR(F2) = 0.048

  • S = 1.03

  • 8005 reflections

  • 523 parameters

  • H-atom parameters constrained

  • Δρmax = 1.32 e Å−3

  • Δρmin = −0.82 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5N1⋯O2Wi 0.90 2.00 2.761 (4) 141
N5—H5N2⋯O6 0.90 1.86 2.722 (4) 160
N6—H6N1⋯O16ii 0.90 1.78 2.676 (4) 176
N6—H6N2⋯O12 0.90 1.95 2.762 (4) 149
O1W—H1W1⋯O7 0.85 2.08 2.891 (3) 160
O1W—H1W2⋯O9iii 0.85 2.53 3.337 (4) 158
O2W—H2W1⋯O14 0.85 2.04 2.887 (4) 176
O2W—H2W2⋯O5 0.85 2.35 3.162 (4) 159
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x-1, -y, -z; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The preparation and characterization of self-assembling systems have been considered by chemists in recent years. A literature review shows that the (pydc)2- ligand can form complexes with transition metals (Aghabozorg, Attar Gharamaleki, Ghadermazi et al., 2007; Aghabozorg, Attar Gharamaleki, Ghasemikhah et al., 2007; Aghabozorg, Motyeian et al., 2007; Aghabozorg, Daneshvar et al., 2007; Sharif et al., 2007). In this work, (pydc)2- acts as tridentate ligand with one N atom of pyridine and two O atoms of carboxylates acting as donors and also has a bridging role between the binuclear units containing Bi1 and Bi2. The binuclear units consist of two BiIII atoms, four (pydc)2- ligands, and one coordinated water molecule, while one (pipzH2)2+ cation and one uncoordinated water molecule are also present in the asymmetric unit (Fig. 1).

Two Bi1—O7—C14—O8—Bi2 bridging bonds between neighboring binuclear units link them together and form several rings with four BiIII atoms, six O atoms and two C atoms (Fig. 2). Atom Bi1 is eight coordinated by two tridentate (pydc)2- ligands, one O atom from the Bi1—O9—Bi2 bridge and one O atom from the neighbouring carboxylate group (Bi1—O14i = 2.971 (3) Å, symmetry code: (i) -x, 1 - y, 1 - z). Atom Bi2 is nine coordinated by two tridentate (pydc)2- ligands, one O atom from the Bi1—O1—Bi2 bridge, one O atom from a coordinated water molecule (Bi2—O1W = 2.960 (3) Å) and one O atom from a neighbouring carboxylate group (Bi2—O8ii = 2.883 (2) Å, symmetry code: (ii) -x, 1 - y, -z). The sum of the van der Waals radii for Bi and O is 3.86 Å, which is significantly longer than the bond distances for Bi1—O14i and Bi2—O8ii. The coordination polyhedron around Bi1 is a distorted bicapped trigonal prism which is nearly eclipsed, in which O1, O7, O9 and O3, O5, O14 form two triangles and N1 and N2 form two caps of the prism. The sum of the bond angles N3—Bi2—O1W (113.37 (8)°), O1W—Bi2—N4 (125.24 (8)°) and N4—Bi2—N3 (121.00 (9)°) is equal to 359.61°, indicating that Bi2 is located in the center of the O1W/N3/N4 plane. Atoms O8, O11, O15 and O1, O9, O13 build two triangles. So, a prism consisting of six O atoms and three caps (N3, N4 and O1W) on its faces is formed around Bi2, that is the coordination polyhedron may be described as a distorted tricapped trigonal prism.

N—H···O hydrogen bonds are formed between (pipzH2)2+ and the carboxylate groups (Table1) and also O—H···O hydrogen bonds are formed between uncoordinated water molecules and the carboxylate groups. In addition, C—H···O contacts with C···O distances ranging from 2.887 (4)Å to 3.656 (4) Å are observed between (pipzH2)2+ cations and carboxylate groups. There are C29—H29B···Cg1 interactions (3.638 (5) Å; x, y + 1, z), where Cg1 is the centroid of the N4/C23—C27 ring and also C32—H32B···Cg2 interactions (3.656 (5) Å; x - 1,y, z), where Cg2 is the centroid of the N2/C9—C13 ring (Fig. 3).

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007); Aghabozorg, Motyeian et al. (2007); Aghabozorg, Daneshvar et al. (2007); Sharif et al. (2007); Sheshmani et al. (2006).

Experimental top

The proton transfer compound (pipzH2)(pydcH)2.3H2O was prepared by reaction of pyridine-2,6-dicarboxylic acid (pydcH2) with piperazine (pipz) (Sheshmani et al., 2006). A solution of Bi(NO3)3.5H2O (242 mg, 0.5 mmol) in water (25 ml) was added to (pipzH2)(pydcH)2.3H2O (253 mg, 1.0 mmol) in 25 ml water and colorless crystals were obtained by slow evaporation of the solvent at room temperature.

Refinement top

H atoms attached to O and N atoms were found in difference Fourier maps, then their distances were normalized to O—H = 0.85, N—H = 0.90 Å along the observed O/N—H vector. H atoms bound to C atoms were placed in calculated positions. All H atoms were then refined as riding with Uiso(H) = 1.2Ueq(C/N) or 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at 50% probability for non-H atoms.
[Figure 2] Fig. 2. Rings of four BiIII atoms within the 1-D coordination polymers.
[Figure 3] Fig. 3. Crystal packing with hydrogen bonds shown as dashed lines.
Poly[piperazinediium [[aquabismuthate(III)]-di-µ-pyridine-2,6-dicarboxylato- bismuthate(III)-di-µ-pyridine-2,6-dicarboxylato] monohydrate] top
Crystal data top
(C4H12N2)[Bi2(C7H3NO4)4(H2O)]·H2OZ = 2
Mr = 1202.56F(000) = 1144
Triclinic, P1Dx = 2.392 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8111 (4) ÅCell parameters from 5207 reflections
b = 12.1660 (5) Åθ = 2.6–29.4°
c = 14.0402 (5) ŵ = 10.62 mm1
α = 96.094 (1)°T = 100 K
β = 93.169 (1)°Prism, colourless
γ = 113.848 (1)°0.15 × 0.15 × 0.10 mm
V = 1669.65 (11) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
8005 independent reflections
Radiation source: fine-focus sealed tube6952 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1414
Tmin = 0.204, Tmax = 0.346k = 1616
22723 measured reflectionsl = 1818
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)] = 0.022Hydrogen site location: difference Fourier map
wR(F2) = 0.048H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.019P)2]
where P = (Fo2 + 2Fc2)/3
8005 reflections(Δ/σ)max = 0.001
523 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = 0.82 e Å3
Crystal data top
(C4H12N2)[Bi2(C7H3NO4)4(H2O)]·H2Oγ = 113.848 (1)°
Mr = 1202.56V = 1669.65 (11) Å3
Triclinic, P1Z = 2
a = 10.8111 (4) ÅMo Kα radiation
b = 12.1660 (5) ŵ = 10.62 mm1
c = 14.0402 (5) ÅT = 100 K
α = 96.094 (1)°0.15 × 0.15 × 0.10 mm
β = 93.169 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
8005 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
6952 reflections with I > 2σ(I)
Tmin = 0.204, Tmax = 0.346Rint = 0.031
22723 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.048H-atom parameters constrained
S = 1.03Δρmax = 1.32 e Å3
8005 reflectionsΔρmin = 0.82 e Å3
523 parameters
Special details top

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
Bi10.187854 (12)0.622892 (10)0.307230 (9)0.01470 (4)
Bi20.184337 (12)0.356548 (10)0.178059 (9)0.01477 (4)
O10.0427 (2)0.3934 (2)0.26028 (18)0.0193 (5)
O20.0375 (3)0.2059 (2)0.23943 (18)0.0225 (5)
O30.4159 (2)0.7303 (2)0.35552 (17)0.0195 (5)
O40.6152 (3)0.7375 (2)0.41582 (19)0.0246 (6)
O50.1821 (3)0.8179 (2)0.39201 (17)0.0202 (5)
O60.2563 (3)1.0190 (2)0.39225 (18)0.0228 (5)
O70.2296 (2)0.5669 (2)0.15750 (17)0.0175 (5)
O80.2740 (3)0.6124 (2)0.01038 (17)0.0207 (5)
O90.0239 (2)0.5885 (2)0.20041 (18)0.0196 (5)
O100.0098 (2)0.7798 (2)0.21948 (19)0.0225 (5)
O110.4218 (2)0.2606 (2)0.15982 (18)0.0203 (5)
O120.6215 (2)0.2613 (2)0.11226 (19)0.0234 (5)
O130.1855 (3)0.4370 (2)0.33567 (17)0.0193 (5)
O140.2198 (3)0.4114 (2)0.48793 (18)0.0228 (5)
O150.2214 (2)0.1481 (2)0.10123 (17)0.0183 (5)
O160.2602 (3)0.0419 (2)0.12412 (18)0.0226 (5)
N10.3057 (3)0.4903 (3)0.3281 (2)0.0165 (6)
N20.2716 (3)0.7927 (2)0.2211 (2)0.0152 (6)
N30.2965 (3)0.4993 (2)0.1700 (2)0.0161 (6)
N40.2525 (3)0.2036 (2)0.2842 (2)0.0164 (6)
C10.0944 (4)0.3157 (3)0.2662 (2)0.0180 (7)
C20.2423 (4)0.3687 (3)0.3098 (2)0.0171 (7)
C30.3090 (4)0.2964 (3)0.3301 (2)0.0191 (7)
H3A0.26270.21050.31750.023*
C40.4432 (4)0.3505 (3)0.3688 (3)0.0221 (7)
H4A0.48990.30210.38410.026*
C50.5101 (4)0.4771 (3)0.3854 (3)0.0204 (7)
H5A0.60330.51650.41040.025*
C60.4356 (3)0.5435 (3)0.3640 (2)0.0173 (7)
C70.4970 (3)0.6814 (3)0.3806 (2)0.0174 (7)
C80.2402 (3)0.9155 (3)0.3569 (3)0.0183 (7)
C90.2945 (3)0.9050 (3)0.2603 (2)0.0160 (7)
C100.3618 (3)1.0040 (3)0.2131 (3)0.0186 (7)
H10A0.37861.08380.24140.022*
C110.4038 (4)0.9842 (3)0.1244 (3)0.0213 (7)
H11A0.45211.05090.09180.026*
C120.3756 (3)0.8668 (3)0.0827 (3)0.0184 (7)
H12A0.40160.85130.02090.022*
C130.3087 (3)0.7735 (3)0.1339 (2)0.0169 (7)
C140.2686 (3)0.6421 (3)0.0956 (2)0.0164 (7)
C150.0753 (4)0.6690 (3)0.2024 (2)0.0181 (7)
C160.2269 (3)0.6196 (3)0.1788 (2)0.0167 (7)
C170.2899 (4)0.6960 (3)0.1640 (3)0.0200 (7)
H17A0.23920.78160.17320.024*
C180.4288 (4)0.6453 (3)0.1355 (3)0.0213 (7)
H18A0.47430.69550.12290.026*
C190.5008 (4)0.5192 (3)0.1255 (3)0.0216 (7)
H19A0.59590.48190.10620.026*
C200.4299 (3)0.4504 (3)0.1445 (2)0.0173 (7)
C210.4988 (3)0.3139 (3)0.1373 (2)0.0169 (7)
C220.2236 (3)0.3715 (3)0.4019 (3)0.0181 (7)
C230.2778 (3)0.2360 (3)0.3722 (2)0.0169 (7)
C240.3469 (3)0.1508 (3)0.4298 (2)0.0182 (7)
H24A0.36930.17490.49070.022*
C250.3832 (3)0.0283 (3)0.3965 (3)0.0191 (7)
H25A0.43010.03250.43480.023*
C260.3498 (3)0.0034 (3)0.3066 (3)0.0183 (7)
H26A0.37020.08580.28340.022*
C270.2863 (3)0.0871 (3)0.2518 (2)0.0167 (7)
C280.2530 (3)0.0622 (3)0.1510 (3)0.0184 (7)
N50.1037 (3)1.1154 (3)0.4887 (2)0.0199 (6)
H5N10.13501.19690.49710.024*
H5N20.17041.09940.46360.024*
C290.0256 (4)1.0593 (3)0.4221 (3)0.0216 (7)
H29A0.00781.08480.35770.026*
H29B0.09311.08760.44710.026*
C300.0819 (4)1.0776 (3)0.5865 (3)0.0210 (7)
H30A0.01731.10650.61590.025*
H30B0.16921.11430.62860.025*
N60.8584 (3)0.0656 (3)0.0345 (2)0.0192 (6)
H6N10.81470.05900.01710.023*
H6N20.78440.11110.07610.023*
C310.9440 (4)0.1308 (3)0.0061 (3)0.0216 (7)
H31A0.88680.20610.01890.026*
H31B0.98300.15340.06320.026*
C320.9431 (4)0.0495 (3)0.0703 (3)0.0231 (8)
H32A0.98230.03120.12870.028*
H32B0.88540.09170.08780.028*
O1W0.0082 (3)0.3774 (2)0.0319 (2)0.0287 (6)
H1W10.08260.42110.06660.043*
H1W20.01350.40620.02110.043*
O2W0.0696 (3)0.6708 (2)0.5000 (2)0.0348 (7)
H2W10.11770.59510.49690.052*
H2W20.01420.69580.45830.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.01464 (7)0.01425 (6)0.01526 (7)0.00582 (5)0.00170 (5)0.00288 (5)
Bi20.01454 (7)0.01311 (6)0.01629 (7)0.00520 (5)0.00116 (5)0.00279 (5)
O10.0178 (12)0.0164 (11)0.0229 (13)0.0061 (10)0.0002 (10)0.0041 (10)
O20.0236 (14)0.0161 (11)0.0245 (13)0.0058 (10)0.0020 (11)0.0011 (10)
O30.0184 (12)0.0182 (11)0.0207 (13)0.0064 (10)0.0001 (10)0.0037 (10)
O40.0189 (13)0.0227 (13)0.0304 (15)0.0072 (11)0.0034 (11)0.0043 (11)
O50.0240 (13)0.0219 (12)0.0168 (12)0.0112 (11)0.0038 (10)0.0043 (10)
O60.0265 (14)0.0198 (12)0.0238 (13)0.0114 (11)0.0052 (11)0.0010 (10)
O70.0166 (12)0.0164 (11)0.0193 (12)0.0065 (10)0.0015 (10)0.0035 (9)
O80.0232 (13)0.0215 (12)0.0180 (12)0.0102 (11)0.0017 (10)0.0016 (10)
O90.0154 (12)0.0173 (11)0.0265 (13)0.0069 (10)0.0014 (10)0.0049 (10)
O100.0180 (13)0.0172 (12)0.0287 (14)0.0043 (10)0.0010 (11)0.0033 (10)
O110.0161 (12)0.0177 (11)0.0258 (13)0.0053 (10)0.0019 (10)0.0048 (10)
O120.0181 (13)0.0197 (12)0.0299 (14)0.0052 (10)0.0018 (11)0.0051 (10)
O130.0245 (13)0.0161 (11)0.0178 (12)0.0091 (10)0.0005 (10)0.0025 (9)
O140.0295 (14)0.0201 (12)0.0177 (13)0.0100 (11)0.0021 (11)0.0000 (10)
O150.0207 (13)0.0157 (11)0.0182 (12)0.0074 (10)0.0007 (10)0.0027 (9)
O160.0294 (14)0.0185 (12)0.0233 (13)0.0122 (11)0.0086 (11)0.0048 (10)
N10.0167 (14)0.0187 (13)0.0154 (14)0.0078 (12)0.0025 (11)0.0057 (11)
N20.0144 (14)0.0173 (13)0.0147 (14)0.0077 (11)0.0016 (11)0.0020 (11)
N30.0174 (14)0.0177 (13)0.0143 (14)0.0079 (11)0.0020 (11)0.0032 (11)
N40.0157 (14)0.0158 (13)0.0181 (14)0.0074 (11)0.0000 (11)0.0014 (11)
C10.0195 (18)0.0192 (16)0.0161 (17)0.0080 (14)0.0023 (14)0.0050 (13)
C20.0215 (18)0.0185 (16)0.0123 (15)0.0089 (14)0.0039 (13)0.0030 (12)
C30.0212 (18)0.0184 (16)0.0193 (17)0.0092 (14)0.0047 (14)0.0034 (13)
C40.0236 (19)0.0238 (17)0.0235 (19)0.0145 (15)0.0005 (15)0.0049 (14)
C50.0173 (17)0.0251 (17)0.0204 (18)0.0100 (14)0.0018 (14)0.0042 (14)
C60.0185 (17)0.0208 (16)0.0136 (16)0.0090 (14)0.0022 (13)0.0040 (13)
C70.0188 (17)0.0200 (16)0.0135 (16)0.0078 (14)0.0013 (13)0.0034 (13)
C80.0159 (17)0.0205 (16)0.0200 (17)0.0092 (14)0.0008 (14)0.0031 (14)
C90.0149 (16)0.0167 (15)0.0175 (17)0.0076 (13)0.0004 (13)0.0029 (13)
C100.0162 (17)0.0150 (15)0.0240 (18)0.0069 (13)0.0034 (14)0.0014 (13)
C110.0173 (17)0.0181 (16)0.0267 (19)0.0050 (14)0.0015 (15)0.0054 (14)
C120.0182 (17)0.0208 (16)0.0182 (17)0.0095 (14)0.0028 (14)0.0050 (13)
C130.0143 (16)0.0173 (15)0.0187 (17)0.0061 (13)0.0007 (13)0.0029 (13)
C140.0107 (15)0.0185 (15)0.0203 (17)0.0065 (13)0.0005 (13)0.0020 (13)
C150.0188 (18)0.0201 (16)0.0178 (17)0.0095 (14)0.0026 (14)0.0058 (13)
C160.0182 (17)0.0163 (15)0.0140 (16)0.0054 (13)0.0025 (13)0.0028 (12)
C170.0189 (17)0.0171 (16)0.0244 (18)0.0077 (14)0.0031 (14)0.0031 (14)
C180.0211 (18)0.0194 (16)0.0275 (19)0.0126 (14)0.0022 (15)0.0027 (14)
C190.0163 (17)0.0231 (17)0.0237 (18)0.0067 (14)0.0018 (14)0.0027 (14)
C200.0186 (17)0.0165 (15)0.0162 (16)0.0071 (14)0.0023 (13)0.0006 (13)
C210.0179 (17)0.0171 (15)0.0154 (16)0.0068 (13)0.0027 (13)0.0028 (13)
C220.0164 (17)0.0182 (16)0.0201 (17)0.0076 (13)0.0009 (13)0.0023 (13)
C230.0146 (16)0.0191 (16)0.0171 (17)0.0076 (13)0.0007 (13)0.0015 (13)
C240.0152 (16)0.0231 (17)0.0150 (16)0.0071 (14)0.0000 (13)0.0009 (13)
C250.0171 (17)0.0194 (16)0.0203 (18)0.0059 (14)0.0021 (14)0.0074 (13)
C260.0175 (17)0.0161 (15)0.0203 (17)0.0064 (13)0.0003 (14)0.0029 (13)
C270.0153 (16)0.0145 (15)0.0199 (17)0.0063 (13)0.0021 (13)0.0015 (13)
C280.0140 (16)0.0170 (15)0.0237 (18)0.0065 (13)0.0017 (14)0.0024 (13)
N50.0190 (15)0.0161 (13)0.0242 (16)0.0061 (12)0.0037 (12)0.0046 (12)
C290.0200 (18)0.0232 (17)0.0218 (18)0.0087 (15)0.0016 (14)0.0054 (14)
C300.0167 (17)0.0198 (16)0.0216 (18)0.0039 (14)0.0002 (14)0.0009 (14)
N60.0178 (15)0.0197 (14)0.0181 (15)0.0060 (12)0.0002 (12)0.0025 (11)
C310.0225 (18)0.0157 (16)0.0247 (19)0.0063 (14)0.0034 (15)0.0015 (14)
C320.0187 (18)0.0221 (17)0.0271 (19)0.0059 (14)0.0016 (15)0.0079 (15)
O1W0.0237 (14)0.0264 (14)0.0319 (15)0.0067 (11)0.0002 (12)0.0035 (12)
O2W0.0361 (17)0.0240 (14)0.0426 (18)0.0106 (13)0.0117 (14)0.0016 (12)
Geometric parameters (Å, º) top
Bi1—O72.266 (2)C8—C91.521 (5)
Bi1—O32.295 (2)C9—C101.390 (5)
Bi1—N22.385 (3)C10—C111.379 (5)
Bi1—N12.456 (3)C10—H10A0.950
Bi1—O92.526 (2)C11—C121.388 (5)
Bi1—O52.565 (2)C11—H11A0.950
Bi1—O12.578 (2)C12—C131.376 (5)
Bi1—O14i2.971 (3)C12—H12A0.950
Bi2—O132.326 (2)C13—C141.505 (4)
Bi2—O112.337 (2)C15—C161.503 (5)
Bi2—N42.414 (3)C16—C171.382 (5)
Bi2—N32.496 (3)C17—C181.388 (5)
Bi2—O12.499 (2)C17—H17A0.950
Bi2—O152.512 (2)C18—C191.398 (5)
Bi2—O92.620 (2)C18—H18A0.950
Bi2—O8ii2.883 (2)C19—C201.379 (5)
Bi2—O1W2.960 (3)C19—H19A0.950
O1—C11.285 (4)C20—C211.510 (5)
O2—C11.227 (4)C22—C231.511 (5)
O3—C71.295 (4)C23—C241.380 (5)
O4—C71.223 (4)C24—C251.397 (5)
O5—C81.266 (4)C24—H24A0.950
O6—C81.242 (4)C25—C261.391 (5)
O7—C141.292 (4)C25—H25A0.950
O8—C141.224 (4)C26—C271.380 (5)
O8—Bi2ii2.883 (2)C26—H26A0.950
O9—C151.306 (4)C27—C281.509 (5)
O10—C151.231 (4)N5—C301.496 (5)
O11—C211.290 (4)N5—C291.497 (4)
O12—C211.228 (4)N5—H5N10.900
O13—C221.267 (4)N5—H5N20.900
O14—C221.244 (4)C29—C30iii1.513 (5)
O14—Bi1i2.971 (3)C29—H29A0.990
O15—C281.260 (4)C29—H29B0.990
O16—C281.252 (4)C30—C29iii1.513 (5)
N1—C61.328 (4)C30—H30A0.990
N1—C21.343 (4)C30—H30B0.990
N2—C131.336 (4)N6—C321.488 (4)
N2—C91.336 (4)N6—C311.505 (4)
N3—C201.328 (4)N6—H6N10.900
N3—C161.335 (4)N6—H6N20.900
N4—C271.333 (4)C31—C32iv1.507 (5)
N4—C231.333 (4)C31—H31A0.990
C1—C21.523 (5)C31—H31B0.990
C2—C31.384 (5)C32—C31iv1.507 (5)
C3—C41.378 (5)C32—H32A0.990
C3—H3A0.950C32—H32B0.990
C4—C51.397 (5)O1W—H1W10.850
C4—H4A0.950O1W—H1W20.850
C5—C61.394 (5)O2W—H2W10.850
C5—H5A0.950O2W—H2W20.850
C6—C71.520 (5)
O7—Bi1—O391.67 (8)C5—C6—C7122.4 (3)
O7—Bi1—N269.13 (9)O4—C7—O3125.1 (3)
O3—Bi1—N271.64 (9)O4—C7—C6119.6 (3)
O7—Bi1—N174.33 (9)O3—C7—C6115.3 (3)
O3—Bi1—N167.54 (9)O6—C8—O5127.0 (3)
N2—Bi1—N1123.21 (9)O6—C8—C9116.3 (3)
O7—Bi1—O975.63 (8)O5—C8—C9116.7 (3)
O3—Bi1—O9150.67 (8)N2—C9—C10120.8 (3)
N2—Bi1—O979.11 (8)N2—C9—C8115.7 (3)
N1—Bi1—O9130.88 (8)C10—C9—C8123.5 (3)
O7—Bi1—O5133.72 (8)C11—C10—C9118.9 (3)
O3—Bi1—O580.95 (8)C11—C10—H10A120.6
N2—Bi1—O565.17 (8)C9—C10—H10A120.6
N1—Bi1—O5139.27 (8)C10—C11—C12120.0 (3)
O9—Bi1—O588.88 (8)C10—C11—H11A120.0
O7—Bi1—O171.85 (8)C12—C11—H11A120.0
O3—Bi1—O1131.37 (8)C13—C12—C11117.7 (3)
N2—Bi1—O1134.97 (8)C13—C12—H12A121.1
N1—Bi1—O164.02 (8)C11—C12—H12A121.1
O9—Bi1—O170.14 (8)N2—C13—C12122.4 (3)
O5—Bi1—O1142.67 (8)N2—C13—C14114.6 (3)
O7—Bi1—O14i142.66 (8)C12—C13—C14122.9 (3)
O3—Bi1—O14i75.43 (8)O8—C14—O7124.1 (3)
N2—Bi1—O14i134.51 (8)O8—C14—C13120.0 (3)
N1—Bi1—O14i68.34 (8)O7—C14—C13115.8 (3)
O9—Bi1—O14i129.79 (8)O10—C15—O9125.5 (3)
O5—Bi1—O14i79.51 (7)O10—C15—C16118.7 (3)
O1—Bi1—O14i90.47 (7)O9—C15—C16115.8 (3)
O13—Bi2—O1190.55 (9)N3—C16—C17121.9 (3)
O13—Bi2—N467.58 (9)N3—C16—C15117.2 (3)
O11—Bi2—N472.05 (9)C17—C16—C15120.8 (3)
O13—Bi2—N372.91 (9)C16—C17—C18118.6 (3)
O11—Bi2—N366.29 (9)C16—C17—H17A120.7
N4—Bi2—N3121.00 (9)C18—C17—H17A120.7
O13—Bi2—O175.37 (8)C17—C18—C19119.1 (3)
O11—Bi2—O1151.73 (8)C17—C18—H18A120.5
N4—Bi2—O179.89 (9)C19—C18—H18A120.5
N3—Bi2—O1129.27 (8)C20—C19—C18118.1 (3)
O13—Bi2—O15132.74 (8)C20—C19—H19A120.9
O11—Bi2—O1579.38 (8)C18—C19—H19A120.9
N4—Bi2—O1565.37 (8)N3—C20—C19122.5 (3)
N3—Bi2—O15138.11 (8)N3—C20—C21115.3 (3)
O1—Bi2—O1592.19 (7)C19—C20—C21122.1 (3)
O13—Bi2—O972.26 (8)O12—C21—O11124.5 (3)
O11—Bi2—O9129.51 (8)O12—C21—C20119.4 (3)
N4—Bi2—O9134.46 (8)O11—C21—C20116.1 (3)
N3—Bi2—O963.32 (8)O14—C22—O13124.5 (3)
O1—Bi2—O969.86 (8)O14—C22—C23119.0 (3)
O15—Bi2—O9145.72 (8)O13—C22—C23116.4 (3)
O13—Bi2—O8ii135.52 (7)N4—C23—C24121.6 (3)
O11—Bi2—O8ii73.14 (8)N4—C23—C22114.2 (3)
N4—Bi2—O8ii137.85 (8)C24—C23—C22124.1 (3)
N3—Bi2—O8ii62.62 (8)C23—C24—C25118.5 (3)
O1—Bi2—O8ii133.56 (8)C23—C24—H24A120.8
O15—Bi2—O8ii85.53 (7)C25—C24—H24A120.8
O9—Bi2—O8ii86.61 (7)C26—C25—C24119.0 (3)
O13—Bi2—O1W139.60 (8)C26—C25—H25A120.5
O11—Bi2—O1W129.27 (8)C24—C25—H25A120.5
N4—Bi2—O1W125.24 (8)C27—C26—C25118.7 (3)
N3—Bi2—O1W113.37 (8)C27—C26—H26A120.7
O1—Bi2—O1W70.76 (8)C25—C26—H26A120.7
O15—Bi2—O1W70.62 (7)N4—C27—C26121.7 (3)
O9—Bi2—O1W75.85 (7)N4—C27—C28115.2 (3)
O8ii—Bi2—O1W64.79 (7)C26—C27—C28123.1 (3)
C1—O1—Bi2127.3 (2)O16—C28—O15125.9 (3)
C1—O1—Bi1121.4 (2)O16—C28—C27117.2 (3)
Bi2—O1—Bi1110.39 (9)O15—C28—C27116.9 (3)
C7—O3—Bi1124.1 (2)C30—N5—C29111.4 (3)
C8—O5—Bi1118.5 (2)C30—N5—H5N1106.3
C14—O7—Bi1122.1 (2)C29—N5—H5N1110.5
C14—O8—Bi2ii140.2 (2)C30—N5—H5N2111.7
C15—O9—Bi1122.0 (2)C29—N5—H5N2111.4
C15—O9—Bi2120.3 (2)H5N1—N5—H5N2105.1
Bi1—O9—Bi2108.23 (9)N5—C29—C30iii110.0 (3)
C21—O11—Bi2123.5 (2)N5—C29—H29A109.7
C22—O13—Bi2122.5 (2)C30iii—C29—H29A109.7
C22—O14—Bi1i147.0 (2)N5—C29—H29B109.7
C28—O15—Bi2119.9 (2)C30iii—C29—H29B109.7
C6—N1—C2120.1 (3)H29A—C29—H29B108.2
C6—N1—Bi1117.1 (2)N5—C30—C29iii109.5 (3)
C2—N1—Bi1122.8 (2)N5—C30—H30A109.8
C13—N2—C9120.1 (3)C29iii—C30—H30A109.8
C13—N2—Bi1116.9 (2)N5—C30—H30B109.8
C9—N2—Bi1122.7 (2)C29iii—C30—H30B109.8
C20—N3—C16119.7 (3)H30A—C30—H30B108.2
C20—N3—Bi2116.9 (2)C32—N6—C31110.7 (3)
C16—N3—Bi2122.9 (2)C32—N6—H6N1116.6
C27—N4—C23120.3 (3)C31—N6—H6N1105.6
C27—N4—Bi2121.4 (2)C32—N6—H6N2111.5
C23—N4—Bi2117.3 (2)C31—N6—H6N2114.5
O2—C1—O1126.6 (3)H6N1—N6—H6N297.4
O2—C1—C2118.3 (3)N6—C31—C32iv109.6 (3)
O1—C1—C2115.1 (3)N6—C31—H31A109.7
N1—C2—C3121.2 (3)C32iv—C31—H31A109.8
N1—C2—C1116.5 (3)N6—C31—H31B109.7
C3—C2—C1122.3 (3)C32iv—C31—H31B109.7
C4—C3—C2119.3 (3)H31A—C31—H31B108.2
C4—C3—H3A120.4N6—C32—C31iv110.3 (3)
C2—C3—H3A120.4N6—C32—H32A109.6
C3—C4—C5119.5 (3)C31iv—C32—H32A109.6
C3—C4—H4A120.3N6—C32—H32B109.6
C5—C4—H4A120.3C31iv—C32—H32B109.6
C6—C5—C4117.8 (3)H32A—C32—H32B108.1
C6—C5—H5A121.1Bi2—O1W—H1W199.6
C4—C5—H5A121.1Bi2—O1W—H1W2130.1
N1—C6—C5122.2 (3)H1W1—O1W—H1W2106.1
N1—C6—C7115.4 (3)H2W1—O2W—H2W2119.0
O13—Bi2—O1—C1124.0 (3)O13—Bi2—N3—C1679.3 (3)
O11—Bi2—O1—C161.7 (3)O11—Bi2—N3—C16177.7 (3)
N4—Bi2—O1—C154.7 (3)N4—Bi2—N3—C16128.7 (2)
N3—Bi2—O1—C1176.7 (3)O1—Bi2—N3—C1625.6 (3)
O15—Bi2—O1—C19.8 (3)O15—Bi2—N3—C16144.6 (2)
O9—Bi2—O1—C1159.9 (3)O9—Bi2—N3—C161.0 (2)
O8ii—Bi2—O1—C195.7 (3)O8ii—Bi2—N3—C1699.7 (3)
O1W—Bi2—O1—C178.4 (3)O1W—Bi2—N3—C1658.0 (3)
O13—Bi2—O1—Bi167.02 (10)O13—Bi2—N4—C27179.2 (3)
O11—Bi2—O1—Bi1129.36 (14)O11—Bi2—N4—C2780.9 (3)
N4—Bi2—O1—Bi1136.30 (11)N3—Bi2—N4—C27127.4 (2)
N3—Bi2—O1—Bi114.30 (15)O1—Bi2—N4—C27102.5 (3)
O15—Bi2—O1—Bi1159.20 (10)O15—Bi2—N4—C275.4 (2)
O9—Bi2—O1—Bi19.11 (8)O9—Bi2—N4—C27150.8 (2)
O8ii—Bi2—O1—Bi173.28 (12)O8ii—Bi2—N4—C2745.2 (3)
O1W—Bi2—O1—Bi190.61 (10)O1W—Bi2—N4—C2744.9 (3)
O7—Bi1—O1—C179.5 (3)O13—Bi2—N4—C2310.5 (2)
O3—Bi1—O1—C13.8 (3)O11—Bi2—N4—C2387.8 (2)
N2—Bi1—O1—C1110.5 (3)N3—Bi2—N4—C2341.3 (3)
N1—Bi1—O1—C11.5 (2)O1—Bi2—N4—C2388.7 (2)
O9—Bi1—O1—C1160.3 (3)O15—Bi2—N4—C23174.1 (3)
O5—Bi1—O1—C1140.2 (2)O9—Bi2—N4—C2340.4 (3)
O14i—Bi1—O1—C167.0 (3)O8ii—Bi2—N4—C23123.5 (2)
O7—Bi1—O1—Bi290.28 (10)O1W—Bi2—N4—C23146.3 (2)
O3—Bi1—O1—Bi2165.93 (9)Bi2—O1—C1—O26.5 (5)
N2—Bi1—O1—Bi259.29 (15)Bi1—O1—C1—O2174.4 (3)
N1—Bi1—O1—Bi2171.27 (13)Bi2—O1—C1—C2172.4 (2)
O9—Bi1—O1—Bi29.44 (9)Bi1—O1—C1—C24.5 (4)
O5—Bi1—O1—Bi250.04 (16)C6—N1—C2—C31.8 (5)
O14i—Bi1—O1—Bi2123.22 (9)Bi1—N1—C2—C3174.4 (2)
O7—Bi1—O3—C779.5 (3)C6—N1—C2—C1178.4 (3)
N2—Bi1—O3—C7146.9 (3)Bi1—N1—C2—C15.3 (4)
N1—Bi1—O3—C77.2 (2)O2—C1—C2—N1172.7 (3)
O9—Bi1—O3—C7142.5 (2)O1—C1—C2—N16.3 (5)
O5—Bi1—O3—C7146.4 (3)O2—C1—C2—C37.6 (5)
O1—Bi1—O3—C712.4 (3)O1—C1—C2—C3173.5 (3)
O14i—Bi1—O3—C765.0 (3)N1—C2—C3—C40.7 (5)
O7—Bi1—O5—C818.4 (3)C1—C2—C3—C4179.5 (3)
O3—Bi1—O5—C865.2 (2)C2—C3—C4—C51.0 (5)
N2—Bi1—O5—C88.7 (2)C3—C4—C5—C61.7 (5)
N1—Bi1—O5—C8104.1 (3)C2—N1—C6—C51.1 (5)
O9—Bi1—O5—C887.2 (2)Bi1—N1—C6—C5175.4 (3)
O1—Bi1—O5—C8141.3 (2)C2—N1—C6—C7179.3 (3)
O14i—Bi1—O5—C8141.9 (3)Bi1—N1—C6—C74.3 (4)
O3—Bi1—O7—C1473.4 (2)C4—C5—C6—N10.7 (5)
N2—Bi1—O7—C143.8 (2)C4—C5—C6—C7178.9 (3)
N1—Bi1—O7—C14139.5 (3)Bi1—O3—C7—O4172.1 (3)
O9—Bi1—O7—C1479.8 (2)Bi1—O3—C7—C67.7 (4)
O5—Bi1—O7—C145.6 (3)N1—C6—C7—O4178.1 (3)
O1—Bi1—O7—C14153.2 (3)C5—C6—C7—O41.5 (5)
O14i—Bi1—O7—C14141.3 (2)N1—C6—C7—O31.6 (4)
O7—Bi1—O9—C15129.3 (3)C5—C6—C7—O3178.7 (3)
O3—Bi1—O9—C1562.6 (3)Bi1—O5—C8—O6174.0 (3)
N2—Bi1—O9—C1558.3 (3)Bi1—O5—C8—C96.9 (4)
N1—Bi1—O9—C15176.9 (2)C13—N2—C9—C102.6 (5)
O5—Bi1—O9—C156.6 (3)Bi1—N2—C9—C10170.4 (2)
O1—Bi1—O9—C15155.1 (3)C13—N2—C9—C8176.3 (3)
O14i—Bi1—O9—C1581.9 (3)Bi1—N2—C9—C810.7 (4)
O7—Bi1—O9—Bi284.45 (9)O6—C8—C9—N2177.4 (3)
O3—Bi1—O9—Bi2151.22 (13)O5—C8—C9—N21.8 (4)
N2—Bi1—O9—Bi2155.47 (11)O6—C8—C9—C101.5 (5)
N1—Bi1—O9—Bi230.64 (15)O5—C8—C9—C10179.3 (3)
O5—Bi1—O9—Bi2139.62 (9)N2—C9—C10—C110.5 (5)
O1—Bi1—O9—Bi28.88 (8)C8—C9—C10—C11178.2 (3)
O14i—Bi1—O9—Bi264.28 (12)C9—C10—C11—C121.6 (5)
O13—Bi2—O9—C1575.6 (2)C10—C11—C12—C131.7 (5)
O11—Bi2—O9—C150.1 (3)C9—N2—C13—C122.5 (5)
N4—Bi2—O9—C15104.6 (3)Bi1—N2—C13—C12170.9 (3)
N3—Bi2—O9—C153.8 (2)C9—N2—C13—C14176.1 (3)
O1—Bi2—O9—C15156.1 (3)Bi1—N2—C13—C1410.5 (4)
O15—Bi2—O9—C15141.7 (2)C11—C12—C13—N20.3 (5)
O8ii—Bi2—O9—C1564.7 (2)C11—C12—C13—C14178.2 (3)
O1W—Bi2—O9—C15129.5 (3)Bi2ii—O8—C14—O7128.7 (3)
O13—Bi2—O9—Bi171.32 (10)Bi2ii—O8—C14—C1351.2 (5)
O11—Bi2—O9—Bi1146.80 (9)Bi1—O7—C14—O8169.4 (2)
N4—Bi2—O9—Bi142.35 (15)Bi1—O7—C14—C1310.5 (4)
N3—Bi2—O9—Bi1150.68 (12)N2—C13—C14—O8166.2 (3)
O1—Bi2—O9—Bi19.18 (8)C12—C13—C14—O812.4 (5)
O15—Bi2—O9—Bi171.42 (16)N2—C13—C14—O713.7 (4)
O8ii—Bi2—O9—Bi1148.38 (9)C12—C13—C14—O7167.7 (3)
O1W—Bi2—O9—Bi183.55 (9)Bi1—O9—C15—O1032.0 (5)
O13—Bi2—O11—C2183.7 (3)Bi2—O9—C15—O10174.4 (3)
N4—Bi2—O11—C21149.8 (3)Bi1—O9—C15—C16149.7 (2)
N3—Bi2—O11—C2112.7 (2)Bi2—O9—C15—C167.4 (4)
O1—Bi2—O11—C21142.7 (2)C20—N3—C16—C171.3 (5)
O15—Bi2—O11—C21142.8 (3)Bi2—N3—C16—C17173.0 (3)
O9—Bi2—O11—C2116.4 (3)C20—N3—C16—C15176.7 (3)
O8ii—Bi2—O11—C2154.3 (2)Bi2—N3—C16—C154.9 (4)
O1W—Bi2—O11—C2188.9 (3)O10—C15—C16—N3173.6 (3)
O11—Bi2—O13—C2267.3 (3)O9—C15—C16—N38.1 (5)
N4—Bi2—O13—C223.0 (2)O10—C15—C16—C178.5 (5)
N3—Bi2—O13—C22132.2 (3)O9—C15—C16—C17169.9 (3)
O1—Bi2—O13—C2287.9 (3)N3—C16—C17—C182.6 (5)
O15—Bi2—O13—C228.7 (3)C15—C16—C17—C18175.3 (3)
O9—Bi2—O13—C22161.0 (3)C16—C17—C18—C191.9 (5)
O8ii—Bi2—O13—C22133.4 (2)C17—C18—C19—C200.1 (5)
O1W—Bi2—O13—C22121.6 (3)C16—N3—C20—C190.7 (5)
O13—Bi2—O15—C283.6 (3)Bi2—N3—C20—C19171.5 (3)
O11—Bi2—O15—C2877.2 (2)C16—N3—C20—C21179.6 (3)
N4—Bi2—O15—C282.2 (2)Bi2—N3—C20—C218.1 (4)
N3—Bi2—O15—C28111.9 (3)C18—C19—C20—N31.3 (5)
O1—Bi2—O15—C2875.6 (2)C18—C19—C20—C21179.1 (3)
O9—Bi2—O15—C28131.8 (2)Bi2—O11—C21—O12167.7 (3)
O8ii—Bi2—O15—C28150.9 (2)Bi2—O11—C21—C2013.3 (4)
O1W—Bi2—O15—C28144.3 (3)N3—C20—C21—O12178.5 (3)
O7—Bi1—N1—C6104.3 (3)C19—C20—C21—O121.1 (5)
O3—Bi1—N1—C65.7 (2)N3—C20—C21—O112.4 (4)
N2—Bi1—N1—C653.0 (3)C19—C20—C21—O11177.9 (3)
O9—Bi1—N1—C6158.5 (2)Bi1i—O14—C22—O13149.2 (3)
O5—Bi1—N1—C636.5 (3)Bi1i—O14—C22—C2331.2 (6)
O1—Bi1—N1—C6178.6 (3)Bi2—O13—C22—O14176.5 (3)
O14i—Bi1—N1—C676.9 (2)Bi2—O13—C22—C233.9 (4)
O7—Bi1—N1—C279.4 (3)C27—N4—C23—C244.3 (5)
O3—Bi1—N1—C2178.0 (3)Bi2—N4—C23—C24164.6 (3)
N2—Bi1—N1—C2130.7 (2)C27—N4—C23—C22175.3 (3)
O9—Bi1—N1—C225.1 (3)Bi2—N4—C23—C2215.9 (4)
O5—Bi1—N1—C2139.9 (2)O14—C22—C23—N4167.1 (3)
O1—Bi1—N1—C22.3 (2)O13—C22—C23—N413.3 (4)
O14i—Bi1—N1—C299.4 (3)O14—C22—C23—C2412.5 (5)
O7—Bi1—N2—C134.3 (2)O13—C22—C23—C24167.2 (3)
O3—Bi1—N2—C1394.9 (2)N4—C23—C24—C254.0 (5)
N1—Bi1—N2—C1349.2 (3)C22—C23—C24—C25175.5 (3)
O9—Bi1—N2—C1382.9 (2)C23—C24—C25—C260.6 (5)
O5—Bi1—N2—C13176.8 (3)C24—C25—C26—C272.4 (5)
O1—Bi1—N2—C1335.8 (3)C23—N4—C27—C261.1 (5)
O14i—Bi1—N2—C13140.6 (2)Bi2—N4—C27—C26167.3 (3)
O7—Bi1—N2—C9177.5 (3)C23—N4—C27—C28179.7 (3)
O3—Bi1—N2—C978.3 (2)Bi2—N4—C27—C2811.3 (4)
N1—Bi1—N2—C9124.0 (2)C25—C26—C27—N42.3 (5)
O9—Bi1—N2—C9103.9 (3)C25—C26—C27—C28176.2 (3)
O5—Bi1—N2—C910.0 (2)Bi2—O15—C28—O16172.0 (3)
O1—Bi1—N2—C9150.9 (2)Bi2—O15—C28—C278.5 (4)
O14i—Bi1—N2—C932.6 (3)N4—C27—C28—O16167.6 (3)
O13—Bi2—N3—C20108.7 (3)C26—C27—C28—O1613.8 (5)
O11—Bi2—N3—C2010.3 (2)N4—C27—C28—O1512.9 (4)
N4—Bi2—N3—C2059.3 (3)C26—C27—C28—O15165.7 (3)
O1—Bi2—N3—C20162.4 (2)C30—N5—C29—C30iii58.4 (4)
O15—Bi2—N3—C2027.4 (3)C29—N5—C30—C29iii58.0 (4)
O9—Bi2—N3—C20172.9 (3)C32—N6—C31—C32iv58.1 (4)
O8ii—Bi2—N3—C2072.2 (2)C31—N6—C32—C31iv58.5 (4)
O1W—Bi2—N3—C20114.0 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x, y+2, z+1; (iv) x2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N1···O2Wiii0.902.002.761 (4)141
N5—H5N2···O60.901.862.722 (4)160
N6—H6N1···O16v0.901.782.676 (4)176
N6—H6N2···O120.901.952.762 (4)149
O1W—H1W1···O70.852.082.891 (3)160
O1W—H1W2···O9ii0.852.533.337 (4)158
O2W—H2W1···O140.852.042.887 (4)176
O2W—H2W2···O50.852.353.162 (4)159
Symmetry codes: (ii) x, y+1, z; (iii) x, y+2, z+1; (v) x1, y, z.

Experimental details

Crystal data
Chemical formula(C4H12N2)[Bi2(C7H3NO4)4(H2O)]·H2O
Mr1202.56
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.8111 (4), 12.1660 (5), 14.0402 (5)
α, β, γ (°)96.094 (1), 93.169 (1), 113.848 (1)
V3)1669.65 (11)
Z2
Radiation typeMo Kα
µ (mm1)10.62
Crystal size (mm)0.15 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.204, 0.346
No. of measured, independent and
observed [I > 2σ(I)] reflections
22723, 8005, 6952
Rint0.031
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.048, 1.03
No. of reflections8005
No. of parameters523
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.32, 0.82

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N1···O2Wi0.902.002.761 (4)141
N5—H5N2···O60.901.862.722 (4)160
N6—H6N1···O16ii0.901.782.676 (4)176
N6—H6N2···O120.901.952.762 (4)149
O1W—H1W1···O70.852.082.891 (3)160
O1W—H1W2···O9iii0.852.533.337 (4)158
O2W—H2W1···O140.852.042.887 (4)176
O2W—H2W2···O50.852.353.162 (4)159
Symmetry codes: (i) x, y+2, z+1; (ii) x1, y, z; (iii) x, y+1, z.
 

References

First citationAghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007). Acta Cryst. E63, m1803–m1804.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007). Acta Cryst. E63, m1710–m1711.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAghabozorg, H., Daneshvar, S., Motyeian, E., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m2468–m2469.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAghabozorg, H., Motyeian, E., Aghajani, Z., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m1754–m1755.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSharif, M. A., Aghabozorg, H. & Moghimi, A. (2007). Acta Cryst. E63, m1599–m1601.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620–o3622.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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