Supramolecular organization via varied coordination modes in tri­aqua(μ-8-hydroxy-7-iodo­quinoline-5-sulfonato)­barium(II) monohydrate

Muthiah, P.T.; Francis, S.; Bocelli, G.; Cantoni, A.

doi:10.1107/S1600536803024322

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Supramolecular organization via varied coordination modes in triaqua(μ-8-hydroxy-7-iodoquinoline-5-sulfonato)barium(II) monohydrate

P. T. Muthiah, S. Francis, G. Bocelli and A. Cantoni

In the crystal structure of [Ba(C₉H₄INO₄S)(H₂O)₃]·H₂O, the asymmetric unit contains a Ba²⁺ ion, an 8-hydroxy-7-iodoquinoline-5-sulfonate anion, three coordinated water molecules and an uncoordinated water molecule. The Ba²⁺ ion has a nine-coordinate monocapped antiprismatic geometry, formed by four O atoms of three different sulfonate groups, the chelating N and O atoms of the oxine ring, and three water molecules. Each sulfonate group bridges three neighbouring Ba²⁺ ions. The organic ligands are stacked over one another, each pair of adjacent members of the stack being related by inversion symmetry. These stacks are crosslinked by Ba²⁺ ions, leading to a three-dimensional network, which is further stabilized by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024322/cf6290sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024322/cf6290Isup2.hkl Contains datablock I

CCDC reference: 227758

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
H-atom completeness 34%
R factor = 0.077
wR factor = 0.236
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.87
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O4W
PLAT707_ALERT_1_A D...A   Calc  13.859(14), Rep   2.849(12), Dev..     786.43 Sigma
              O2W  -O1      1.555   1.655
PLAT707_ALERT_1_A D...A   Calc  14.910(13), Rep   3.151(11), Dev..     904.54 Sigma
              O2W  -O3      1.555   1.655
PLAT707_ALERT_1_A D...A   Calc  18.925(13), Rep   2.788(12), Dev..    1241.31 Sigma
              O1W  -O4      1.555   1.545
PLAT707_ALERT_1_A D...A   Calc  22.033(14), Rep   2.793(11), Dev..    1374.29 Sigma
              O2W  -O4      1.555   1.645
PLAT707_ALERT_1_A D...A   Calc    32.68(2), Rep   2.834(13), Dev..    1492.30 Sigma
              O4W  -O2W     1.555   2.757
PLAT707_ALERT_1_A D...A   Calc    31.08(2), Rep   2.918(17), Dev..    1408.10 Sigma
              O4W  -O3W     1.555   2.757
PLAT707_ALERT_1_A D...A   Calc    32.68(2), Rep   2.834(13), Dev..    1492.30 Sigma
              O2W  -O4W     1.555   2.757

Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      7.075
            Test value =      5.600
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               3329
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3825
           Completeness (_total/calc)             87.03%
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.46
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       7.07 e/A   3
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O4W      =       2.79 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O2W    ..  O4W      =       2.83 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.208     0.318
            Tmin and Tmax expected:      0.169     0.318
            RR =      1.228
            Please check that your absorption correction is appropriate.
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight           558.43
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           S        32.07    1.00   32.07
           O        16.00    8.00  127.99
           N        14.01    1.00   14.01
           I       126.90    1.00  126.90
           Ba      137.33    1.00  137.33
           H         1.01    4.00    4.03
           C        12.01    9.00  108.10
           Calculated formula weight              550.43
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     558.43
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.23
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         Ba
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C9 H12 Ba1 I1 N1 O8 S1
            Atom count from the _atom_site data:  C9 H4 Ba1 I1 N1 O8 S1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C9 H12 Ba I N O8 S
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         18.00     18.00    0.00
           H         24.00      8.00   16.00
           Ba         2.00      2.00    0.00
           I          2.00      2.00    0.00
           N          2.00      2.00    0.00
           O         16.00     16.00    0.00
           S          2.00      2.00    0.00

   9 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

  15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: SHELXL97.

triaqua(µ-8-hydroxy-7-iodoquinoline-5-sulfonato)barium(II) monohydrate top

Crystal data top

[Ba(C₉H₄INO₄S)(H₂O)₃]·H₂O	Z = 2
M_r = 558.43	F(000) = 524
Triclinic, P1	D_x = 2.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.600 (3) Å	Cell parameters from 8112 reflections
b = 10.089 (2) Å	θ = 2.0–28.3°
c = 10.261 (3) Å	µ = 4.78 mm⁻¹
α = 89.60 (3)°	T = 293 K
β = 77.52 (2)°	Plate, yellow
γ = 85.63 (3)°	0.39 × 0.33 × 0.24 mm
V = 765.9 (4) Å³

Data collection top

Bruker SMART CCD diffractometer	3329 independent reflections
Radiation source: fine-focus sealed tube	2911 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
T_min = 0.208, T_max = 0.318	k = −12→13
8112 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1968P)²]
3329 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 7.08 e Å⁻³
0 restraints	Δρ_min = −1.59 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ba	−0.21121 (7)	0.92337 (5)	0.39398 (5)	0.0303 (2)
I	0.32111 (12)	0.33865 (7)	0.07916 (6)	0.0498 (3)
S	0.3150 (3)	0.8091 (2)	0.3729 (2)	0.0304 (6)
O1	0.3810 (13)	0.8384 (8)	0.2322 (7)	0.054 (3)
O1W	0.0178 (12)	1.1026 (8)	0.2534 (8)	0.051 (3)
O2	0.1351 (10)	0.8744 (7)	0.4271 (8)	0.044 (2)
O2W	−0.4442 (11)	1.0756 (8)	0.2494 (8)	0.049 (3)
O3	0.4380 (9)	0.8485 (6)	0.4549 (7)	0.0366 (19)
O3W	−0.1231 (14)	0.8705 (9)	0.1178 (9)	0.064 (3)
O4	0.2479 (9)	0.2279 (6)	0.3826 (7)	0.0347 (19)
N1	0.1980 (11)	0.3596 (8)	0.6200 (7)	0.034 (2)
C2	0.1797 (16)	0.4225 (10)	0.7354 (9)	0.042 (3)
C3	0.2018 (18)	0.5533 (11)	0.7480 (11)	0.048 (3)
C4	0.2424 (14)	0.6310 (10)	0.6316 (9)	0.039 (3)
C5	0.2994 (12)	0.6365 (8)	0.3817 (9)	0.029 (2)
C6	0.3141 (13)	0.5643 (8)	0.2654 (8)	0.032 (3)
C7	0.2961 (13)	0.4321 (9)	0.2624 (9)	0.032 (3)
C8	0.2591 (12)	0.3568 (9)	0.3805 (8)	0.029 (2)
C9	0.2604 (12)	0.5684 (8)	0.5067 (8)	0.028 (2)
C10	0.2388 (11)	0.4293 (8)	0.5045 (7)	0.026 (2)
O4W	0.2312 (17)	0.8859 (15)	0.0091 (11)	0.107 (5)
H2	0.1497	0.3735	0.8132	0.051*
H3	0.1905	0.5915	0.8319	0.057*
H4	0.2569	0.7214	0.6374	0.046*
H6	0.3376	0.6091	0.1847	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba	0.0340 (4)	0.0272 (4)	0.0312 (4)	−0.0070 (2)	−0.0087 (2)	0.0029 (2)
I	0.0850 (6)	0.0405 (5)	0.0258 (4)	−0.0138 (4)	−0.0130 (3)	−0.0001 (3)
S	0.0385 (11)	0.0245 (10)	0.0295 (10)	−0.0072 (8)	−0.0087 (9)	0.0043 (8)
O1	0.094 (7)	0.039 (4)	0.029 (3)	−0.021 (4)	−0.007 (4)	0.007 (3)
O1W	0.062 (5)	0.050 (4)	0.043 (4)	−0.019 (4)	−0.013 (4)	0.006 (3)
O2	0.044 (4)	0.042 (4)	0.052 (4)	0.011 (3)	−0.025 (3)	−0.013 (3)
O2W	0.055 (5)	0.044 (4)	0.045 (4)	−0.004 (3)	−0.005 (3)	0.011 (3)
O3	0.042 (4)	0.033 (3)	0.039 (3)	−0.012 (3)	−0.015 (3)	0.009 (3)
O3W	0.090 (7)	0.055 (5)	0.047 (5)	−0.015 (5)	−0.013 (5)	0.003 (4)
O4	0.050 (4)	0.027 (3)	0.031 (3)	−0.009 (3)	−0.015 (3)	0.002 (2)
N1	0.048 (4)	0.035 (4)	0.021 (3)	−0.009 (3)	−0.007 (3)	0.011 (3)
C2	0.073 (7)	0.039 (5)	0.016 (4)	−0.014 (5)	−0.010 (4)	0.002 (3)
C3	0.070 (7)	0.041 (6)	0.032 (5)	−0.018 (5)	−0.006 (5)	0.002 (4)
C4	0.049 (5)	0.037 (5)	0.031 (4)	−0.009 (4)	−0.008 (4)	−0.002 (4)
C5	0.035 (4)	0.022 (4)	0.029 (4)	−0.004 (3)	−0.005 (3)	0.003 (3)
C6	0.047 (5)	0.027 (4)	0.022 (4)	−0.006 (4)	−0.007 (4)	0.006 (3)
C7	0.043 (5)	0.029 (4)	0.025 (4)	−0.010 (4)	−0.009 (3)	−0.001 (3)
C8	0.036 (4)	0.031 (4)	0.021 (4)	−0.008 (3)	−0.009 (3)	0.003 (3)
C9	0.031 (4)	0.031 (4)	0.023 (4)	−0.002 (3)	−0.006 (3)	−0.001 (3)
C10	0.030 (4)	0.032 (4)	0.015 (3)	−0.007 (3)	−0.003 (3)	0.001 (3)
O4W	0.098 (9)	0.155 (12)	0.051 (6)	0.038 (8)	0.006 (6)	0.033 (7)

Geometric parameters (Å, º) top

Ba—O1W	2.782 (9)	N1—C2	1.323 (12)
Ba—O2	2.734 (8)	N1—C10	1.363 (10)
Ba—O2W	2.896 (8)	C2—C3	1.353 (15)
Ba—O3W	2.813 (9)	C3—C4	1.414 (14)
Ba—O3ⁱ	2.766 (7)	C4—C9	1.408 (12)
Ba—O4ⁱⁱ	2.721 (7)	C5—C6	1.382 (12)
Ba—N1ⁱⁱ	2.853 (8)	C5—C9	1.435 (12)
Ba—O2ⁱⁱⁱ	2.926 (8)	C6—C7	1.352 (12)
Ba—O3ⁱⁱⁱ	2.995 (7)	C7—C8	1.413 (12)
I—C7	2.074 (9)	C8—C10	1.445 (11)
S—O1	1.458 (7)	C9—C10	1.426 (11)
S—O2	1.467 (8)	C2—H2	0.930
S—O3	1.463 (7)	C3—H3	0.930
S—C5	1.755 (8)	C4—H4	0.930
O4—C8	1.309 (11)	C6—H6	0.930

I···O1W^iv	3.630 (9)	O3W···O2W	3.147 (13)
I···O4	3.248 (7)	O3W···O1W	3.104 (13)
I···O3W^v	3.558 (10)	O3W···O4W	2.699 (17)
I···H2^vi	3.275	O3W···I^v	3.558 (10)
S···H4	2.802	O4···I	3.248 (7)
O1···O2W^vii	2.849 (12)	O4···O1W^iv	2.789 (11)
O1···O4W	2.792 (14)	O4···O3^xi	3.240 (10)
O1W···O3W	3.104 (13)	O4···O2W^xii	2.794 (11)
O1W···I^viii	3.630 (9)	O4···N1	2.723 (10)
O1W···O2	3.097 (11)	O4W···O3W^ix	2.919 (17)
O1W···C4ⁱⁱⁱ	3.279 (13)	O4W···O2W^ix	2.834 (14)
O1W···O4^viii	2.789 (11)	O4W···O1	2.792 (14)
O1W···O2ⁱⁱⁱ	3.237 (11)	O4W···O3W	2.699 (17)
O2···C4	3.385 (12)	O1···H6	2.429
O2···O1W	3.097 (11)	O1W···H4ⁱⁱⁱ	2.687
O2···O1Wⁱⁱⁱ	3.237 (11)	O2···H4	2.915
O2W···O3ⁱ	3.151 (10)	O3···H4	2.484
O2W···O3W	3.147 (13)	O3W···H2ⁱⁱ	2.568
O2W···O3ⁱⁱⁱ	3.146 (11)	N1···O4	2.723 (10)
O2W···Sⁱ	3.447 (9)	C4···O3	3.097 (12)
O2W···O1ⁱ	2.849 (12)	C4···O1Wⁱⁱⁱ	3.279 (13)
O2W···O4W^ix	2.834 (14)	C4···O2	3.385 (12)
O2W···O4^x	2.794 (11)	H2···I^xiii	3.275
O3···O2Wⁱⁱⁱ	3.146 (11)	H2···O3Wⁱⁱ	2.568
O3···C4	3.097 (12)	H4···S	2.802
O3···O2W^vii	3.151 (10)	H4···O3	2.484
O3···O4^xi	3.240 (10)	H4···O1Wⁱⁱⁱ	2.687
O3W···C2ⁱⁱ	3.323 (13)	H4···O2	2.915
O3W···O4W^ix	2.919 (17)	H6···O1	2.429

O1W—Ba—O2	68.3 (2)	O2—S—C5	108.3 (4)
O1W—Ba—O2W	77.4 (2)	O3—S—C5	109.8 (4)
O1W—Ba—O3W	67.4 (3)	Ba—O2—S	146.3 (5)
O1W—Ba—O3ⁱ	144.9 (2)	Ba—O2—Baⁱⁱⁱ	109.1 (2)
O1W—Ba—O4ⁱⁱ	140.0 (2)	Baⁱⁱⁱ—O2—S	102.6 (4)
O1W—Ba—N1ⁱⁱ	131.0 (2)	Ba^vii—O3—S	133.0 (4)
O1W—Ba—O2ⁱⁱⁱ	69.0 (2)	Baⁱⁱⁱ—O3—S	99.7 (3)
O1W—Ba—O3ⁱⁱⁱ	89.2 (2)	Ba^vii—O3—Baⁱⁱⁱ	106.4 (2)
O2—Ba—O2W	145.4 (2)	Baⁱⁱ—O4—C8	124.8 (5)
O2—Ba—O3W	94.7 (3)	C2—N1—C10	119.1 (8)
O2—Ba—O3ⁱ	146.8 (2)	Baⁱⁱ—N1—C2	121.2 (6)
O2—Ba—O4ⁱⁱ	76.2 (2)	Baⁱⁱ—N1—C10	118.9 (5)
O2—Ba—N1ⁱⁱ	82.9 (2)	N1—C2—C3	124.4 (9)
O2—Ba—O2ⁱⁱⁱ	70.9 (2)	C2—C3—C4	119.0 (10)
O2—Ba—O3ⁱⁱⁱ	118.2 (2)	C3—C4—C9	118.4 (9)
O2W—Ba—O3W	66.9 (3)	S—C5—C6	119.3 (7)
O2W—Ba—O3ⁱ	67.6 (2)	S—C5—C9	122.1 (6)
O2W—Ba—O4ⁱⁱ	137.7 (2)	C6—C5—C9	118.5 (7)
O2W—Ba—N1ⁱⁱ	118.2 (2)	C5—C6—C7	123.6 (8)
O2ⁱⁱⁱ—Ba—O2W	101.7 (2)	I—C7—C6	118.8 (6)
O2W—Ba—O3ⁱⁱⁱ	64.5 (2)	I—C7—C8	119.4 (6)
O3ⁱ—Ba—O3W	100.0 (3)	C6—C7—C8	121.8 (8)
O3W—Ba—O4ⁱⁱ	135.0 (2)	O4—C8—C7	124.0 (8)
O3W—Ba—N1ⁱⁱ	76.9 (2)	O4—C8—C10	119.6 (7)
O2ⁱⁱⁱ—Ba—O3W	136.4 (3)	C7—C8—C10	116.3 (8)
O3ⁱⁱⁱ—Ba—O3W	129.5 (2)	C4—C9—C5	123.8 (8)
O3ⁱ—Ba—O4ⁱⁱ	72.4 (2)	C4—C9—C10	118.0 (7)
O3ⁱ—Ba—N1ⁱⁱ	71.8 (2)	C5—C9—C10	118.2 (7)
O2ⁱⁱⁱ—Ba—O3ⁱ	114.6 (2)	N1—C10—C8	117.4 (7)
O3ⁱ—Ba—O3ⁱⁱⁱ	73.64 (19)	N1—C10—C9	121.0 (7)
O4ⁱⁱ—Ba—N1ⁱⁱ	58.4 (2)	C8—C10—C9	121.6 (7)
O2ⁱⁱⁱ—Ba—O4ⁱⁱ	82.7 (2)	N1—C2—H2	117.8
O3ⁱⁱⁱ—Ba—O4ⁱⁱ	91.79 (19)	C3—C2—H2	117.8
O2ⁱⁱⁱ—Ba—N1ⁱⁱ	137.5 (2)	C2—C3—H3	120.5
O3ⁱⁱⁱ—Ba—N1ⁱⁱ	139.8 (2)	C4—C3—H3	120.5
O2ⁱⁱⁱ—Ba—O3ⁱⁱⁱ	47.3 (2)	C3—C4—H4	120.8
O1—S—O2	112.5 (5)	C9—C4—H4	120.7
O1—S—O3	111.9 (5)	C5—C6—H6	118.2
O1—S—C5	106.1 (4)	C7—C6—H6	118.2
O2—S—O3	108.3 (4)

O1W—Ba—O2—S	−84.5 (8)	O3—S—O2—Baⁱⁱⁱ	14.3 (4)
O1W—Ba—O2—Baⁱⁱⁱ	74.3 (3)	C5—S—O2—Ba	−67.2 (8)
O2W—Ba—O2—S	−76.0 (9)	C5—S—O2—Baⁱⁱⁱ	133.2 (4)
O2W—Ba—O2—Baⁱⁱⁱ	82.9 (5)	O1—S—O3—Ba^vii	−12.7 (6)
O3W—Ba—O2—S	−21.1 (8)	O1—S—O3—Baⁱⁱⁱ	110.7 (4)
O3W—Ba—O2—Baⁱⁱⁱ	137.8 (3)	O2—S—O3—Ba^vii	−137.2 (5)
O3ⁱ—Ba—O2—S	95.1 (8)	O2—S—O3—Baⁱⁱⁱ	−13.8 (4)
O3ⁱ—Ba—O2—Baⁱⁱⁱ	−106.0 (4)	C5—S—O3—Ba^vii	104.8 (5)
O4ⁱⁱ—Ba—O2—S	114.2 (8)	C5—S—O3—Baⁱⁱⁱ	−131.8 (4)
O4ⁱⁱ—Ba—O2—Baⁱⁱⁱ	−86.9 (3)	O1—S—C5—C6	−12.0 (10)
N1ⁱⁱ—Ba—O2—S	55.0 (8)	O1—S—C5—C9	172.1 (8)
N1ⁱⁱ—Ba—O2—Baⁱⁱⁱ	−146.1 (3)	O2—S—C5—C6	109.0 (8)
O2ⁱⁱⁱ—Ba—O2—S	−158.9 (8)	O2—S—C5—C9	−67.0 (9)
O2ⁱⁱⁱ—Ba—O2—Baⁱⁱⁱ	0.0 (2)	O3—S—C5—C6	−133.0 (8)
O3ⁱⁱⁱ—Ba—O2—S	−161.3 (7)	O3—S—C5—C9	51.0 (9)
O3ⁱⁱⁱ—Ba—O2—Baⁱⁱⁱ	−2.4 (3)	Baⁱⁱ—O4—C8—C7	173.4 (7)
O1W—Ba—O3ⁱ—Sⁱ	57.2 (6)	Baⁱⁱ—O4—C8—C10	−4.5 (12)
O2—Ba—O3ⁱ—Sⁱ	−122.3 (5)	C10—N1—C2—C3	−1.2 (18)
O2W—Ba—O3ⁱ—Sⁱ	52.3 (5)	Baⁱⁱ—N1—C2—C3	168.7 (10)
O3W—Ba—O3ⁱ—Sⁱ	−7.5 (5)	C2—N1—C10—C8	179.5 (9)
O1W—Ba—O4ⁱⁱ—C8ⁱⁱ	−124.0 (7)	C2—N1—C10—C9	−0.5 (14)
O2—Ba—O4ⁱⁱ—C8ⁱⁱ	−96.4 (7)	Baⁱⁱ—N1—C10—C8	9.4 (10)
O2W—Ba—O4ⁱⁱ—C8ⁱⁱ	92.2 (7)	Baⁱⁱ—N1—C10—C9	−170.6 (6)
O3W—Ba—O4ⁱⁱ—C8ⁱⁱ	−13.7 (9)	N1—C2—C3—C4	2 (2)
O1W—Ba—N1ⁱⁱ—C2ⁱⁱ	−51.2 (9)	C2—C3—C4—C9	−0.8 (18)
O1W—Ba—N1ⁱⁱ—C10ⁱⁱ	139.0 (6)	C3—C4—C9—C10	−0.8 (15)
O2—Ba—N1ⁱⁱ—C2ⁱⁱ	−104.1 (8)	C3—C4—C9—C5	179.3 (10)
O2—Ba—N1ⁱⁱ—C10ⁱⁱ	86.0 (7)	C9—C5—C6—C7	−0.9 (15)
O2W—Ba—N1ⁱⁱ—C2ⁱⁱ	46.8 (9)	S—C5—C6—C7	−177.0 (8)
O2W—Ba—N1ⁱⁱ—C10ⁱⁱ	−123.1 (6)	C6—C5—C9—C4	179.9 (10)
O3W—Ba—N1ⁱⁱ—C2ⁱⁱ	−7.6 (8)	S—C5—C9—C4	−4.0 (14)
O3W—Ba—N1ⁱⁱ—C10ⁱⁱ	−177.5 (7)	S—C5—C9—C10	176.0 (7)
O1W—Ba—O2ⁱⁱⁱ—Baⁱⁱⁱ	−73.4 (3)	C6—C5—C9—C10	0.0 (13)
O1W—Ba—O2ⁱⁱⁱ—Sⁱⁱⁱ	118.5 (4)	C5—C6—C7—I	179.8 (8)
O2—Ba—O2ⁱⁱⁱ—Baⁱⁱⁱ	0.0 (2)	C5—C6—C7—C8	0.4 (16)
O2—Ba—O2ⁱⁱⁱ—Sⁱⁱⁱ	−168.2 (4)	I—C7—C8—C10	−178.4 (6)
O2W—Ba—O2ⁱⁱⁱ—Baⁱⁱⁱ	−144.9 (3)	I—C7—C8—O4	3.6 (13)
O2W—Ba—O2ⁱⁱⁱ—Sⁱⁱⁱ	47.0 (4)	C6—C7—C8—O4	−177.1 (9)
O3W—Ba—O2ⁱⁱⁱ—Baⁱⁱⁱ	−76.2 (4)	C6—C7—C8—C10	0.9 (14)
O3W—Ba—O2ⁱⁱⁱ—Sⁱⁱⁱ	115.6 (4)	O4—C8—C10—N1	−3.7 (13)
O1W—Ba—O3ⁱⁱⁱ—Sⁱⁱⁱ	−70.6 (3)	C7—C8—C10—C9	−1.8 (13)
O2—Ba—O3ⁱⁱⁱ—Sⁱⁱⁱ	−5.8 (4)	O4—C8—C10—C9	176.3 (8)
O2W—Ba—O3ⁱⁱⁱ—Sⁱⁱⁱ	−147.0 (4)	C7—C8—C10—N1	178.2 (8)
O3W—Ba—O3ⁱⁱⁱ—Sⁱⁱⁱ	−130.0 (4)	C4—C9—C10—N1	1.4 (13)
O1—S—O2—Ba	49.7 (9)	C5—C9—C10—C8	1.3 (13)
O1—S—O2—Baⁱⁱⁱ	−109.9 (4)	C4—C9—C10—C8	−178.6 (9)
O3—S—O2—Ba	173.8 (7)	C5—C9—C10—N1	−178.7 (8)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z; (vi) x, y, z−1; (vii) x+1, y, z; (viii) x, y+1, z; (ix) −x, −y+2, −z; (x) x−1, y+1, z; (xi) −x+1, −y+1, −z+1; (xii) x+1, y−1, z; (xiii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3Wⁱⁱ	0.93	2.57	3.323 (13)	139
C4—H4···O3	0.93	2.48	3.097 (12)	124
C6—H6···O1	0.93	2.43	2.855 (12)	108
O2w···O1^vii			2.849 (12)
O2w···O3^vii			3.151 (11)
O1w···O4^iv			2.788 (12)
O2w···O4^xii			2.793 (11)
O4w···O2w^xiv			2.834 (13)
O4w···O3w^xiv			2.918 (17)
O2w···O4w^xiv			2.834 (13)
O4w···O1			2.792 (16)
O4w···O3w			2.699 (17)
O1w···O3w			3.104 (13)
O2w···O3w			3.147 (12)
O1w···O2			3.097 (11)

Symmetry codes: (ii) −x, −y+1, −z+1; (iv) x, y−1, z; (vii) x+1, y, z; (xii) x+1, y−1, z; (xiv) −x+2, −y, −z+2.

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