The structures of the isomorphous potassium and rubidium salts of 4-nitro­benzoic acid and an overview of the metal complex stereochemistries of the alkali metal salt series with this ligand

4-Nitro­benzoic acid (PNBA) has proved to be a useful ligand for the preparation of metal complexes but the known structures of the alkali metal salts of PNBA do not include the rubidium salt. The structures of the isomorphous potassium and rubidium polymeric coordination complexes with PNBA, namely poly[μ₂-aqua-aqua-μ₃-(4-nitro­benzoato)-potassium], [K(C₇H₄N₂O₂)(H₂O)₂]_n, (I), and poly[μ₃-aqua-aqua-μ₅-(4-nitro­ben­zo­ato)-rubidium], [Rb(C₇H₄N₂O₂)(H₂O)₂]_n, (II), have been determined. In (I), the very distorted KO₆ coordination sphere about the K⁺ centres in the repeat unit comprise two bridging nitro O-atom donors, a single bridging carboxyl­ate O-atom donor and two water mol­ecules, one of which is bridging. In Rb complex (II), the same basic MO₆ coordination is found in the repeat unit, but it is expanded to RbO₉ through a slight increase in the accepted Rb—O bond-length range and includes an additional Rb—O_{carboxyl­ate} bond, completing a bidentate O,O′-chelate inter­action, and additional bridging Rb—O_nitro and Rb—O_water bonds. The comparative K—O and Rb—O bond-length ranges are 2.7352 (14)–3.0051 (14) and 2.884 (2)–3.182 (2) Å, respectively. The structure of (II) is also isomorphous, as well as isostructural, with the known structure of the nine-coordinate caesium 4-nitro­benzoate analogue, (III), in which the Cs—O bond-length range is 3.047 (4)–3.338 (4) Å. In all three complexes, common basic polymeric extensions are found, including two different centrosymmetric bridging inter­actions through both water and nitro groups, as well as extensions along c through the para-related carboxyl­ate group, giving a two-dimensional structure in (I). In (II) and (III), three-dimensional structures are generated through additional bridges involving the nitro and water O atoms. In all three structures, the two water mol­ecules are involved in similar intra-polymer O—H...O hydrogen-bonding inter­actions to both carboxyl­ate and water O-atom acceptors. A comparison of the varied coordination behaviour of the full set of Li–Cs salts with 4-nitro­benzoic acid is also made.

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SIR92 (Altomare et al., 1993) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

(I) Poly[µ₂-aqua-aqua-µ₃-(4-nitrobenzoato)-potassium]

Crystal data

[K(C7H4N2O2)(H2O)2]	F(000) = 496
Mr = 241.24	Dx = 1.669 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1787 reflections
a = 5.8217 (4) Å	θ = 3.6–28.4°
b = 6.9692 (5) Å	µ = 0.56 mm^−1
c = 23.8602 (16) Å	T = 200 K
β = 97.299 (6)°	Plate, colourless
V = 960.23 (12) Å^3	0.30 × 0.25 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer	1886 independent reflections
Radiation source: Enhance (Mo) X-ray source	1755 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 16.077 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −5→8
Tmin = 0.945, Tmax = 0.980	l = −25→29
3638 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0335P)^2 + 0.1983P] where P = (Fo^2 + 2Fc^2)/3
1886 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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

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 (Ų)

	x	y	z	Uiso*/Ueq
K1	0.77670 (6)	0.69041 (6)	1.02388 (1)	0.0276 (1)
O1W	0.7292 (2)	0.9884 (2)	0.94571 (5)	0.0356 (4)
O2W	0.7330 (2)	0.30012 (19)	1.01672 (5)	0.0370 (4)
O11	1.0168 (3)	0.6385 (2)	0.63127 (5)	0.0437 (5)
O12	0.7106 (2)	0.4571 (3)	0.60516 (6)	0.0514 (5)
O41	0.4839 (3)	0.4220 (3)	0.88176 (6)	0.0512 (5)
O42	0.8214 (3)	0.5415 (2)	0.90923 (6)	0.0452 (5)
N4	0.6699 (3)	0.4893 (2)	0.87230 (6)	0.0311 (5)
C1	0.7928 (3)	0.5361 (2)	0.70211 (7)	0.0209 (5)
C2	0.5842 (3)	0.4621 (2)	0.71540 (7)	0.0247 (5)
C3	0.5418 (3)	0.4481 (2)	0.77096 (8)	0.0248 (5)
C4	0.7122 (3)	0.5086 (2)	0.81307 (7)	0.0227 (5)
C5	0.9195 (3)	0.5860 (2)	0.80152 (7)	0.0233 (5)
C6	0.9576 (3)	0.6003 (2)	0.74560 (7)	0.0218 (5)
C11	0.8449 (3)	0.5455 (3)	0.64141 (7)	0.0292 (5)
H2	0.46970	0.42070	0.68590	0.0300*
H3	0.39930	0.39810	0.78000	0.0300*
H5	1.03270	0.62830	0.83110	0.0280*
H6	1.09820	0.65460	0.73670	0.0260*
H11W	0.59450	0.98250	0.92560	0.0530*
H12W	0.81490	1.01440	0.92060	0.0530*
H21W	0.74160	0.24130	1.04820	0.0550*
H22W	0.72240	0.21050	0.99140	0.0550*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0331 (2)	0.0256 (2)	0.0239 (2)	0.0001 (2)	0.0034 (2)	−0.0004 (2)
O1W	0.0388 (7)	0.0417 (8)	0.0262 (7)	−0.0009 (6)	0.0043 (5)	0.0039 (6)
O2W	0.0593 (8)	0.0268 (7)	0.0238 (6)	−0.0026 (7)	0.0011 (6)	0.0046 (6)
O11	0.0629 (9)	0.0411 (9)	0.0311 (8)	−0.0084 (8)	0.0212 (7)	−0.0019 (6)
O12	0.0420 (8)	0.0806 (12)	0.0294 (8)	0.0082 (8)	−0.0037 (6)	−0.0264 (8)
O41	0.0514 (9)	0.0649 (11)	0.0418 (8)	−0.0068 (8)	0.0231 (7)	0.0122 (8)
O42	0.0664 (9)	0.0480 (9)	0.0211 (7)	−0.0090 (8)	0.0055 (6)	−0.0036 (6)
N4	0.0429 (9)	0.0255 (8)	0.0265 (8)	0.0026 (7)	0.0111 (7)	0.0042 (7)
C1	0.0253 (8)	0.0139 (8)	0.0228 (8)	0.0052 (7)	0.0006 (6)	−0.0004 (6)
C2	0.0268 (8)	0.0183 (8)	0.0269 (9)	−0.0007 (7)	−0.0051 (7)	−0.0009 (7)
C3	0.0208 (8)	0.0185 (8)	0.0352 (10)	−0.0009 (7)	0.0043 (6)	0.0034 (7)
C4	0.0309 (8)	0.0173 (8)	0.0205 (8)	0.0031 (7)	0.0060 (7)	0.0034 (7)
C5	0.0268 (8)	0.0199 (8)	0.0220 (8)	−0.0008 (7)	−0.0014 (6)	−0.0003 (7)
C6	0.0223 (8)	0.0194 (8)	0.0237 (9)	−0.0010 (7)	0.0028 (6)	0.0009 (7)
C11	0.0366 (9)	0.0275 (10)	0.0228 (9)	0.0126 (9)	0.0010 (7)	−0.0023 (8)

Geometric parameters (Å, º)

K1—O1W	2.7816 (14)	O2W—H22W	0.8700
K1—O2W	2.7352 (14)	N4—C4	1.471 (2)
K1—O42	2.9681 (15)	C1—C2	1.393 (2)
K1—O2W^i	3.0029 (12)	C1—C6	1.394 (2)
K1—O41^i	2.9752 (17)	C1—C11	1.518 (2)
K1—O11^ii	3.0051 (14)	C2—C3	1.382 (3)
O11—C11	1.242 (2)	C3—C4	1.385 (2)
O12—C11	1.252 (2)	C4—C5	1.381 (2)
O41—N4	1.227 (2)	C5—C6	1.384 (2)
O42—N4	1.220 (2)	C2—H2	0.9500
O1W—H11W	0.8700	C3—H3	0.9500
O1W—H12W	0.8500	C5—H5	0.9500
O2W—H21W	0.8500	C6—H6	0.9500
O1W—K1—O2W	134.43 (4)	K1^i—O2W—H22W	79.00
O1W—K1—O42	69.87 (4)	O41—N4—O42	123.70 (16)
O1W—K1—O2W^i	75.95 (4)	O41—N4—C4	118.10 (15)
O1W—K1—O41^i	133.41 (5)	O42—N4—C4	118.20 (16)
O1W—K1—O11^ii	105.75 (4)	C2—C1—C6	119.13 (15)
O2W—K1—O42	67.24 (4)	C2—C1—C11	121.26 (15)
O2W—K1—O2W^i	85.49 (4)	C6—C1—C11	119.61 (15)
O2W—K1—O41^i	74.52 (5)	C1—C2—C3	120.77 (16)
O2W—K1—O11^ii	118.51 (4)	C2—C3—C4	118.39 (16)
O2W^i—K1—O42	84.78 (4)	N4—C4—C5	118.98 (15)
O41^i—K1—O42	135.91 (5)	C3—C4—C5	122.52 (16)
O11^ii—K1—O42	147.02 (5)	N4—C4—C3	118.50 (15)
O2W^i—K1—O41^i	70.85 (4)	C4—C5—C6	118.14 (15)
O2W^i—K1—O11^ii	126.86 (4)	C1—C6—C5	121.00 (16)
O11^ii—K1—O41^i	71.70 (5)	O11—C11—C1	118.17 (15)
K1—O2W—K1^i	94.51 (4)	O12—C11—C1	117.06 (16)
K1^iii—O11—C11	94.25 (11)	O11—C11—O12	124.78 (16)
K1^i—O41—N4	141.87 (11)	C1—C2—H2	120.00
K1—O42—N4	129.04 (13)	C3—C2—H2	120.00
H11W—O1W—H12W	101.00	C2—C3—H3	121.00
K1—O1W—H11W	110.00	C4—C3—H3	121.00
K1—O1W—H12W	128.00	C4—C5—H5	121.00
K1^i—O2W—H21W	104.00	C6—C5—H5	121.00
K1—O2W—H21W	115.00	C1—C6—H6	119.00
K1—O2W—H22W	139.00	C5—C6—H6	120.00
H21W—O2W—H22W	105.00
O1W—K1—O2W—K1^i	−65.28 (6)	K1^i—O41—N4—C4	177.52 (15)
O42—K1—O2W—K1^i	−86.23 (5)	K1—O42—N4—O41	−28.5 (2)
O2W^i—K1—O2W—K1^i	0.00 (5)	K1—O42—N4—C4	151.36 (11)
O41^i—K1—O2W—K1^i	71.36 (4)	O41—N4—C4—C3	−0.7 (2)
O11^ii—K1—O2W—K1^i	129.94 (4)	O41—N4—C4—C5	179.30 (17)
O1W—K1—O42—N4	−86.38 (14)	O42—N4—C4—C3	179.45 (15)
O2W—K1—O42—N4	77.84 (14)	O42—N4—C4—C5	−0.5 (2)
O2W^i—K1—O42—N4	−9.45 (14)	C6—C1—C2—C3	−1.4 (2)
O41^i—K1—O42—N4	45.96 (16)	C11—C1—C2—C3	177.75 (15)
O11^ii—K1—O42—N4	−174.44 (12)	C2—C1—C6—C5	2.0 (2)
O1W—K1—O2W^i—K1^i	138.03 (4)	C11—C1—C6—C5	−177.18 (15)
O2W—K1—O2W^i—K1^i	0.00 (4)	C2—C1—C11—O11	169.32 (16)
O42—K1—O2W^i—K1^i	67.51 (4)	C2—C1—C11—O12	−11.1 (3)
O1W—K1—O41^i—N4^i	70.9 (3)	C6—C1—C11—O11	−11.5 (3)
O2W—K1—O41^i—N4^i	−66.6 (2)	C6—C1—C11—O12	168.09 (17)
O42—K1—O41^i—N4^i	−36.3 (3)	C1—C2—C3—C4	−0.3 (2)
O1W—K1—O11^ii—C11^ii	72.22 (12)	C2—C3—C4—N4	−178.47 (13)
O2W—K1—O11^ii—C11^ii	−119.01 (11)	C2—C3—C4—C5	1.5 (2)
O42—K1—O11^ii—C11^ii	149.37 (11)	N4—C4—C5—C6	179.03 (13)
K1^iii—O11—C11—O12	41.0 (2)	C3—C4—C5—C6	−1.0 (2)
K1^iii—O11—C11—C1	−139.42 (15)	C4—C5—C6—C1	−0.8 (2)
K1^i—O41—N4—O42	−2.7 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O12^iv	0.87	1.84	2.6994 (17)	170
O1W—H12W···O11^v	0.85	1.88	2.7101 (19)	165
O2W—H21W···O12^vi	0.85	1.96	2.785 (2)	162
O2W—H22W···O1W^vii	0.87	1.90	2.7534 (18)	170

Symmetry codes: (iv) −x+1, y+1/2, −z+3/2; (v) −x+2, y+1/2, −z+3/2; (vi) x, −y+1/2, z+1/2; (vii) x, y−1, z.

(II) Poly[µ₃-aqua-aqua-µ₅-(4-nitrobenzoato)-rubidium]

Crystal data

[Rb(C7H4N2O2)(H2O)2]	F(000) = 568
Mr = 287.61	Dx = 1.910 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1174 reflections
a = 5.9355 (5) Å	θ = 3.5–28.5°
b = 7.0456 (7) Å	µ = 4.96 mm^−1
c = 24.204 (2) Å	T = 200 K
β = 98.739 (8)°	Plate, colourless
V = 1000.44 (16) Å^3	0.31 × 0.24 × 0.10 mm
Z = 4

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer	1969 independent reflections
Radiation source: Enhance (Mo) X-ray source	1692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.077 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −7→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −7→8
Tmin = 0.549, Tmax = 0.980	l = −28→29
3439 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0438P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
1969 reflections	Δρmax = 0.51 e Å^−3
137 parameters	Δρmin = −0.51 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0184 (13)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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

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 (Ų)

	x	y	z	Uiso*/Ueq
Rb1	0.78049 (5)	0.69598 (4)	1.02561 (1)	0.0255 (1)
O1W	0.7211 (4)	0.9980 (4)	0.94096 (11)	0.0354 (8)
O2W	0.7393 (4)	0.2888 (3)	1.01744 (11)	0.0337 (8)
O11	1.0358 (4)	0.6237 (4)	0.63766 (11)	0.0383 (9)
O12	0.7228 (4)	0.4612 (4)	0.60615 (10)	0.0374 (9)
O41	0.4706 (5)	0.4209 (5)	0.87570 (12)	0.0519 (10)
O42	0.8054 (5)	0.5305 (4)	0.90717 (11)	0.0437 (10)
N4	0.6575 (5)	0.4828 (4)	0.86862 (13)	0.0310 (10)
C1	0.7987 (5)	0.5306 (4)	0.70310 (13)	0.0186 (9)
C2	0.5929 (5)	0.4550 (5)	0.71350 (14)	0.0231 (10)
C3	0.5446 (5)	0.4405 (4)	0.76745 (15)	0.0235 (10)
C4	0.7062 (5)	0.5016 (4)	0.81099 (13)	0.0212 (10)
C5	0.9124 (5)	0.5805 (5)	0.80252 (14)	0.0236 (10)
C6	0.9564 (5)	0.5940 (5)	0.74803 (13)	0.0215 (9)
C11	0.8583 (6)	0.5394 (5)	0.64466 (15)	0.0244 (10)
H2	0.48390	0.41280	0.68310	0.0280*
H3	0.40340	0.38960	0.77440	0.0280*
H5	1.01980	0.62390	0.83300	0.0280*
H6	1.09650	0.64730	0.74110	0.0260*
H11W	0.57380	0.99300	0.92080	0.0530*
H12W	0.80120	1.03010	0.91800	0.0530*
H21W	0.74790	0.23000	1.04900	0.0500*
H22W	0.72870	0.19920	0.99220	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rb1	0.0287 (2)	0.0251 (2)	0.0233 (2)	−0.0002 (1)	0.0059 (1)	−0.0004 (2)
O1W	0.0353 (13)	0.0451 (16)	0.0268 (15)	−0.0013 (12)	0.0076 (11)	0.0027 (13)
O2W	0.0494 (16)	0.0275 (14)	0.0246 (14)	−0.0020 (11)	0.0069 (12)	0.0045 (11)
O11	0.0453 (15)	0.0437 (16)	0.0295 (15)	−0.0112 (13)	0.0172 (12)	−0.0049 (13)
O12	0.0357 (14)	0.0540 (17)	0.0222 (14)	0.0036 (12)	0.0032 (11)	−0.0130 (13)
O41	0.0537 (17)	0.069 (2)	0.0381 (17)	−0.0099 (16)	0.0234 (14)	0.0118 (16)
O42	0.0633 (18)	0.0499 (18)	0.0185 (14)	−0.0014 (14)	0.0081 (13)	−0.0027 (13)
N4	0.0446 (18)	0.0286 (16)	0.0216 (17)	0.0024 (14)	0.0110 (14)	0.0030 (14)
C1	0.0243 (16)	0.0133 (15)	0.0179 (17)	−0.0003 (13)	0.0026 (13)	−0.0002 (13)
C2	0.0280 (17)	0.0173 (16)	0.0226 (18)	−0.0031 (14)	−0.0004 (14)	0.0004 (14)
C3	0.0227 (16)	0.0205 (16)	0.0282 (19)	−0.0022 (14)	0.0071 (13)	0.0032 (16)
C4	0.0298 (17)	0.0181 (16)	0.0163 (17)	0.0023 (13)	0.0058 (14)	0.0031 (14)
C5	0.0274 (17)	0.0204 (17)	0.0216 (18)	−0.0012 (14)	−0.0006 (13)	−0.0008 (15)
C6	0.0197 (15)	0.0209 (16)	0.0241 (18)	−0.0014 (13)	0.0042 (13)	−0.0009 (15)
C11	0.0279 (18)	0.0214 (17)	0.0245 (19)	0.0083 (15)	0.0059 (14)	−0.0013 (15)

Geometric parameters (Å, º)

Rb1—O1W	2.938 (3)	O2W—H21W	0.8600
Rb1—O2W	2.884 (2)	O2W—H22W	0.8700
Rb1—O42	3.119 (3)	N4—C4	1.473 (4)
Rb1—O2W^i	3.105 (2)	C1—C2	1.390 (4)
Rb1—O41^i	3.112 (3)	C1—C6	1.396 (4)
Rb1—O2W^ii	3.182 (2)	C1—C11	1.511 (5)
Rb1—O42^ii	3.165 (3)	C2—C3	1.383 (5)
Rb1—O11^iii	3.165 (3)	C3—C4	1.382 (5)
Rb1—O12^iii	3.155 (3)	C4—C5	1.388 (4)
O11—C11	1.243 (4)	C5—C6	1.386 (5)
O12—C11	1.262 (4)	C2—H2	0.9500
O41—N4	1.228 (4)	C3—H3	0.9500
O42—N4	1.227 (4)	C5—H5	0.9500
O1W—H11W	0.9300	C6—H6	0.9500
O1W—H12W	0.8200
O1W—Rb1—O2W	132.29 (8)	Rb1^iv—O12—C11	90.3 (2)
O1W—Rb1—O42	69.34 (7)	Rb1^i—O41—N4	138.5 (2)
O1W—Rb1—O2W^i	74.52 (7)	Rb1—O42—N4	132.3 (2)
O1W—Rb1—O41^i	134.93 (8)	Rb1—O42—Rb1^ii	81.81 (6)
O1W—Rb1—O2W^ii	76.45 (6)	Rb1^ii—O42—N4	131.5 (2)
O1W—Rb1—O42^ii	136.48 (7)	H11W—O1W—H12W	104.00
O1W—Rb1—O11^iii	107.34 (7)	Rb1—O1W—H11W	110.00
O1W—Rb1—O12^iii	82.16 (7)	Rb1—O1W—H12W	131.00
O2W—Rb1—O42	65.19 (7)	Rb1^i—O2W—H21W	104.00
O2W—Rb1—O2W^i	86.66 (6)	Rb1—O2W—H21W	115.00
O2W—Rb1—O41^i	75.16 (8)	Rb1—O2W—H22W	140.00
O2W—Rb1—O2W^ii	94.70 (6)	H21W—O2W—H22W	105.00
O2W—Rb1—O42^ii	65.47 (7)	Rb1^ii—O2W—H22W	77.00
O2W—Rb1—O11^iii	118.86 (7)	Rb1^ii—O2W—H21W	112.00
O2W—Rb1—O12^iii	142.00 (7)	Rb1^i—O2W—H22W	80.00
O2W^i—Rb1—O42	83.56 (7)	O41—N4—O42	123.3 (3)
O41^i—Rb1—O42	134.56 (8)	O42—N4—C4	118.4 (3)
O2W^ii—Rb1—O42	62.72 (7)	O41—N4—C4	118.4 (3)
O42—Rb1—O42^ii	98.19 (7)	C2—C1—C11	121.5 (3)
O11^iii—Rb1—O42	148.68 (7)	C2—C1—C6	119.0 (3)
O12^iii—Rb1—O42	151.50 (7)	C6—C1—C11	119.5 (3)
O2W^i—Rb1—O41^i	72.51 (7)	C1—C2—C3	120.9 (3)
O2W^i—Rb1—O2W^ii	141.53 (7)	C2—C3—C4	118.6 (3)
O2W^i—Rb1—O42^ii	147.60 (7)	C3—C4—C5	122.5 (3)
O2W^i—Rb1—O11^iii	126.57 (7)	N4—C4—C3	118.8 (3)
O2W^i—Rb1—O12^iii	89.16 (6)	N4—C4—C5	118.7 (3)
O2W^ii—Rb1—O41^i	144.83 (7)	C4—C5—C6	117.8 (3)
O41^i—Rb1—O42^ii	84.10 (8)	C1—C6—C5	121.2 (3)
O11^iii—Rb1—O41^i	70.81 (7)	O11—C11—O12	124.5 (3)
O12^iii—Rb1—O41^i	67.59 (8)	O11—C11—C1	118.1 (3)
O2W^ii—Rb1—O42^ii	61.38 (7)	O12—C11—C1	117.4 (3)
O2W^ii—Rb1—O11^iii	86.04 (6)	C1—C2—H2	120.00
O2W^ii—Rb1—O12^iii	111.30 (6)	C3—C2—H2	120.00
O11^iii—Rb1—O42^ii	61.88 (7)	C2—C3—H3	121.00
O12^iii—Rb1—O42^ii	102.54 (7)	C4—C3—H3	121.00
O11^iii—Rb1—O12^iii	41.06 (7)	C4—C5—H5	121.00
Rb1—O2W—Rb1^i	93.34 (6)	C6—C5—H5	121.00
Rb1—O2W—Rb1^ii	85.30 (6)	C1—C6—H6	119.00
Rb1^i—O2W—Rb1^ii	141.53 (9)	C5—C6—H6	119.00
Rb1^iv—O11—C11	90.2 (2)
O1W—Rb1—O2W—Rb1^i	−65.51 (10)	O1W—Rb1—O42^ii—Rb1^ii	−68.52 (11)
O1W—Rb1—O2W—Rb1^ii	75.94 (9)	O1W—Rb1—O42^ii—N4^ii	72.8 (3)
O42—Rb1—O2W—Rb1^i	−84.45 (8)	O2W—Rb1—O42^ii—Rb1^ii	57.88 (7)
O42—Rb1—O2W—Rb1^ii	57.00 (7)	O2W—Rb1—O42^ii—N4^ii	−160.8 (3)
O2W^i—Rb1—O2W—Rb1^i	0.00 (8)	O42—Rb1—O42^ii—Rb1^ii	0.00 (8)
O2W^i—Rb1—O2W—Rb1^ii	141.45 (7)	O42—Rb1—O42^ii—N4^ii	141.3 (3)
O41^i—Rb1—O2W—Rb1^i	72.78 (7)	O1W—Rb1—O11^iii—C11^iii	73.8 (2)
O41^i—Rb1—O2W—Rb1^ii	−145.77 (8)	O2W—Rb1—O11^iii—C11^iii	−118.5 (2)
O2W^ii—Rb1—O2W—Rb1^i	−141.45 (7)	O42—Rb1—O11^iii—C11^iii	152.4 (2)
O2W^ii—Rb1—O2W—Rb1^ii	0.00 (7)	O1W—Rb1—O12^iii—C11^iii	−146.7 (2)
O42^ii—Rb1—O2W—Rb1^i	163.01 (9)	O2W—Rb1—O12^iii—C11^iii	55.3 (2)
O42^ii—Rb1—O2W—Rb1^ii	−55.54 (7)	O42—Rb1—O12^iii—C11^iii	−146.4 (2)
O11^iii—Rb1—O2W—Rb1^i	130.49 (7)	Rb1^iv—O11—C11—O12	40.4 (4)
O11^iii—Rb1—O2W—Rb1^ii	−88.06 (7)	Rb1^iv—O11—C11—C1	−139.2 (3)
O12^iii—Rb1—O2W—Rb1^i	84.35 (11)	Rb1^iv—O12—C11—O11	−40.5 (4)
O12^iii—Rb1—O2W—Rb1^ii	−134.21 (9)	Rb1^iv—O12—C11—C1	139.0 (3)
O1W—Rb1—O42—N4	−82.5 (3)	Rb1^i—O41—N4—O42	−5.7 (6)
O1W—Rb1—O42—Rb1^ii	136.78 (8)	Rb1^i—O41—N4—C4	174.6 (2)
O2W—Rb1—O42—N4	82.7 (3)	Rb1—O42—N4—O41	−30.2 (5)
O2W—Rb1—O42—Rb1^ii	−58.09 (7)	Rb1—O42—N4—C4	149.5 (2)
O2W^i—Rb1—O42—N4	−6.6 (3)	Rb1^ii—O42—N4—O41	93.0 (4)
O2W^i—Rb1—O42—Rb1^ii	−147.38 (7)	Rb1^ii—O42—N4—C4	−87.3 (3)
O41^i—Rb1—O42—N4	51.0 (3)	O41—N4—C4—C3	−3.1 (4)
O41^i—Rb1—O42—Rb1^ii	−89.76 (11)	O41—N4—C4—C5	176.7 (3)
O2W^ii—Rb1—O42—N4	−167.5 (3)	O42—N4—C4—C3	177.2 (3)
O2W^ii—Rb1—O42—Rb1^ii	51.78 (6)	O42—N4—C4—C5	−3.0 (4)
O42^ii—Rb1—O42—N4	140.8 (3)	C6—C1—C2—C3	−0.7 (5)
O42^ii—Rb1—O42—Rb1^ii	0.00 (8)	C11—C1—C2—C3	177.3 (3)
O11^iii—Rb1—O42—N4	−172.1 (2)	C2—C1—C6—C5	0.9 (5)
O11^iii—Rb1—O42—Rb1^ii	47.18 (15)	C11—C1—C6—C5	−177.1 (3)
O12^iii—Rb1—O42—N4	−82.8 (3)	C2—C1—C11—O11	173.8 (3)
O12^iii—Rb1—O42—Rb1^ii	136.44 (12)	C2—C1—C11—O12	−5.8 (5)
O1W—Rb1—O2W^i—Rb1^i	135.69 (9)	C6—C1—C11—O11	−8.3 (5)
O2W—Rb1—O2W^i—Rb1^i	0.00 (7)	C6—C1—C11—O12	172.1 (3)
O42—Rb1—O2W^i—Rb1^i	65.39 (7)	C1—C2—C3—C4	−0.5 (5)
O1W—Rb1—O41^i—N4^i	66.1 (4)	C2—C3—C4—N4	−178.8 (3)
O2W—Rb1—O41^i—N4^i	−69.8 (4)	C2—C3—C4—C5	1.4 (5)
O42—Rb1—O41^i—N4^i	−40.3 (4)	N4—C4—C5—C6	179.0 (3)
O1W—Rb1—O2W^ii—Rb1^ii	−132.43 (8)	C3—C4—C5—C6	−1.2 (5)
O2W—Rb1—O2W^ii—Rb1^ii	0.00 (7)	C4—C5—C6—C1	0.1 (5)
O42—Rb1—O2W^ii—Rb1^ii	−58.93 (7)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O12^v	0.93	1.80	2.720 (3)	169
O1W—H12W···O11^vi	0.82	1.89	2.706 (4)	174
O2W—H21W···O12^vii	0.86	1.95	2.790 (4)	163
O2W—H22W···O1W^viii	0.87	1.88	2.752 (4)	176

Symmetry codes: (v) −x+1, y+1/2, −z+3/2; (vi) −x+2, y+1/2, −z+3/2; (vii) x, −y+1/2, z+1/2; (viii) x, y−1, z.