Dipotassium ethane-1,1-diylbis­(diazeniumdiolate) monohydrate

Arulsamy, N.; Bohle, D.S.

doi:10.1107/S1600536805008822

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Dipotassium ethane-1,1-diylbis(diazeniumdiolate) monohydrate

N. Arulsamy and D. S. Bohle

The ethane-1,1-bis(diazeniumdiolate) anion in the title compound, 2K⁺·C₂H₄N₄O₄^2-·H₂O, acts as a complex bridging ligand. Both the N and the O atoms of the diazeniumdiolate substituents are coordinated to the K⁺ cations, revealing the delocalization of a negative charge over the four-atom groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008822/hk6000sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008822/hk6000Isup2.hkl Contains datablock I

CCDC reference: 270452

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.033
wR factor = 0.084
Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT120_ALERT_1_C Reported SPGR R-3     Inconsistent with Explicit      R-3R
PLAT128_ALERT_4_C Non-standard setting of Space group R-3     ....    R-3r
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O1W
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         K1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT731_ALERT_1_C Bond    Calc    2.644(3), Rep  2.6436(13) ......       2.31 su-Rat
              K1   -O2      1.555   3.655
PLAT731_ALERT_1_C Bond    Calc    2.675(3), Rep  2.6748(13) ......       2.31 su-Rat
              K1   -O3      1.555   4.656
PLAT731_ALERT_1_C Bond    Calc   3.8633(9), Rep  3.8632(19) ......       2.11 su-Rat
              K1   -K1      1.555   2.545
PLAT731_ALERT_1_C Bond    Calc    2.725(3), Rep  2.7248(14) ......       2.14 su-Rat
              K2   -O3      1.555   4.656
PLAT731_ALERT_1_C Bond    Calc    1.284(4), Rep  1.2841(19) ......       2.11 su-Rat
              N1   -N2      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc    2.644(3), Rep  2.6436(13) ......       2.31 su-Rat
              O2   -K1      1.555   2.545
PLAT731_ALERT_1_C Bond    Calc    1.304(4), Rep  1.3038(19) ......       2.11 su-Rat
              O3   -N3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc    2.675(3), Rep  2.6748(13) ......       2.31 su-Rat
              O3   -K1      1.555   4.656
PLAT731_ALERT_1_C Bond    Calc    2.725(3), Rep  2.7248(14) ......       2.14 su-Rat
              O3   -K2      1.555   4.656
PLAT731_ALERT_1_C Bond    Calc    1.475(5), Rep    1.475(2) ......       2.50 su-Rat
              N3   -C1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc    1.509(8), Rep    1.510(3) ......       2.67 su-Rat
              C1   -C2      1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    16.8(13), Rep     16.7(6) ......       2.17 su-Rat
              O1W  -K1   -H1A     1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    125.5(3), Rep  125.46(14) ......       2.14 su-Rat
              N2   -N1   -O1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    124.9(3), Rep  124.88(14) ......       2.14 su-Rat
              N4   -N3   -O3      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    119.1(3), Rep  119.06(14) ......       2.14 su-Rat
              N4   -N3   -C1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    116.0(3), Rep  115.93(13) ......       2.31 su-Rat
              O3   -N3   -C1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    113.2(3), Rep  113.20(14) ......       2.14 su-Rat
              N3   -N4   -O4      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    104.7(3), Rep  104.70(13) ......       2.31 su-Rat
              N1   -C1   -N3      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      106(3), Rep   105.5(13) ......       2.31 su-Rat
              N1   -C1   -H1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(3), Rep   109.3(12) ......       2.50 su-Rat
              N3   -C1   -H1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      111(3), Rep   111.2(12) ......       2.50 su-Rat
              C2   -C1   -H1      1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      134(6), Rep      134(2) ......       3.00 su-Rat
              K2   -O1W  -H1B     1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      113(6), Rep      113(2) ......       3.00 su-Rat
              K1   -O1W  -H1B     1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc     -1.5(5), Rep     -1.5(2) ......       2.50 su-Rat
              O1  -N1  -N2  -O2     1.555   1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc   -178.7(3), Rep -178.69(14) ......       2.14 su-Rat
              O2  -N2  -N1  -C1     1.555   1.555   1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       2.09 Ratio

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  35 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Potassium ethane-1,1-bis(diazeniumdiolate) monohydrate top

Crystal data top

2K⁺·C₂H₄N₄O₄⁻·H₂O	D_x = 1.750 Mg m⁻³
M_r = 244.31	Mo Kα radiation, λ = 0.71073 Å
Rhombohedral, R3	Cell parameters from 73 reflections
Hall symbol: -P 3*	θ = 4.6–12.5°
a = 14.2510 (12) Å	µ = 1.02 mm⁻¹
α = 116.402 (7)°	T = 298 K
V = 1390.9 (8) Å³	Block, colorless
Z = 6	0.42 × 0.36 × 0.32 mm
F(000) = 744

Data collection top

Bruker P4 diffractometer	2106 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 30.0°, θ_min = 2.7°
ω scans	h = −10→20
Absorption correction: ψ scan (SHELXS97; Sheldrick, 1997)	k = −19→4
T_min = 0.667, T_max = 0.721	l = −10→20
3377 measured reflections	3 standard reflections every 97 reflections
2631 independent reflections	intensity decay: 1%

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0342P)² + 0.3737P] where P = (F_o² + 2F_c²)/3
2631 reflections	(Δ/σ)_max = 0.002
130 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

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

	x	y	z	U_iso*/U_eq
K1	0.90238 (5)	0.30342 (5)	0.69897 (5)	0.03230 (10)
K2	0.58697 (5)	0.20833 (6)	0.68414 (5)	0.04354 (12)
O1	0.61100 (18)	0.1977 (2)	0.49229 (17)	0.0589 (5)
N1	0.47586 (17)	0.06177 (18)	0.32332 (18)	0.0298 (3)
N2	0.46426 (19)	−0.03067 (18)	0.22672 (19)	0.0336 (3)
O2	0.60514 (18)	0.02657 (18)	0.31424 (19)	0.0426 (3)
O3	0.24404 (19)	−0.15571 (18)	0.26357 (19)	0.0427 (3)
N3	0.26492 (18)	−0.04584 (18)	0.28590 (19)	0.0312 (3)
N4	0.2527 (2)	0.0304 (2)	0.3604 (2)	0.0382 (3)
O4	0.21527 (18)	−0.01325 (18)	0.41182 (18)	0.0427 (3)
C1	0.3179 (2)	0.0001 (3)	0.2304 (2)	0.0349 (4)
H1	0.227 (3)	−0.110 (3)	0.102 (3)	0.044 (6)*
C2	0.3512 (4)	0.1357 (4)	0.2684 (4)	0.0658 (7)
H2A	0.3849	0.1587	0.2288	0.099*
H2B	0.4433	0.2417	0.3920	0.099*
H2C	0.2466	0.0930	0.2085	0.099*
O1W	0.9071 (2)	0.5121 (2)	0.8896 (2)	0.0536 (4)
H1A	0.925 (4)	0.533 (4)	0.848 (4)	0.072 (8)*
H1B	1.001 (5)	0.601 (5)	0.994 (5)	0.085 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.03165 (18)	0.03532 (18)	0.03501 (18)	0.02650 (16)	0.02813 (16)	0.02866 (17)
K2	0.0382 (2)	0.0434 (2)	0.0371 (2)	0.0315 (2)	0.03081 (19)	0.02889 (19)
O1	0.0324 (7)	0.0507 (9)	0.0267 (6)	0.0293 (7)	0.0196 (6)	0.0174 (7)
N1	0.0263 (6)	0.0295 (6)	0.0278 (6)	0.0217 (6)	0.0217 (6)	0.0217 (6)
N2	0.0366 (7)	0.0320 (7)	0.0357 (7)	0.0277 (7)	0.0304 (7)	0.0265 (7)
O2	0.0432 (7)	0.0456 (7)	0.0591 (8)	0.0390 (7)	0.0433 (7)	0.0426 (7)
O3	0.0598 (8)	0.0479 (7)	0.0618 (9)	0.0468 (7)	0.0547 (8)	0.0476 (7)
N3	0.0304 (7)	0.0342 (7)	0.0340 (7)	0.0266 (6)	0.0268 (6)	0.0273 (6)
N4	0.0397 (8)	0.0412 (8)	0.0449 (8)	0.0339 (7)	0.0361 (8)	0.0343 (8)
O4	0.0476 (7)	0.0464 (7)	0.0481 (7)	0.0380 (7)	0.0428 (7)	0.0376 (7)
C1	0.0364 (8)	0.0466 (10)	0.0399 (9)	0.0351 (8)	0.0326 (8)	0.0366 (9)
C2	0.098 (2)	0.099 (2)	0.116 (2)	0.0911 (19)	0.097 (2)	0.100 (2)
O1W	0.0523 (9)	0.0429 (8)	0.0416 (8)	0.0311 (8)	0.0385 (8)	0.0322 (8)

Geometric parameters (Å, º) top

K1—O2ⁱ	2.6436 (13)	N1—N2	1.2841 (19)
K1—O3ⁱⁱ	2.6748 (13)	N1—C1	1.465 (2)
K1—O1	2.7933 (18)	N1—K2^iv	3.3577 (17)
K1—O4ⁱⁱ	2.8420 (16)	N2—O2	1.290 (2)
K1—N2ⁱⁱⁱ	2.889 (2)	N2—K1^vii	2.889 (2)
K1—O4^iv	2.9374 (15)	N2—K2^iv	3.168 (2)
K1—O1W	2.9506 (18)	N2—K2ⁱⁱ	3.2554 (16)
K1—O2	2.969 (3)	O2—K1^v	2.6436 (13)
K1—O2ⁱⁱⁱ	3.173 (3)	O2—K2^iv	2.7943 (16)
K1—K2^iv	3.7814 (7)	O2—K1^vii	3.173 (3)
K1—K1^v	3.8632 (19)	O2—K2ⁱⁱ	3.2675 (15)
K1—K1ⁱ	3.8632 (19)	O3—N3	1.3038 (19)
K1—H1A	2.76 (3)	O3—K1ⁱⁱ	2.6748 (13)
K2—O1W	2.722 (3)	O3—K2ⁱⁱ	2.7248 (14)
K2—O3ⁱⁱ	2.7248 (14)	N3—N4	1.283 (2)
K2—O2^vi	2.7944 (16)	N3—C1	1.475 (2)
K2—O1	2.8507 (18)	N4—O4	1.291 (2)
K2—O4	3.006 (2)	O4—K1ⁱⁱ	2.8420 (16)
K2—N4	3.117 (2)	O4—K1^vi	2.9373 (15)
K2—N2^vi	3.168 (2)	C1—C2	1.510 (3)
K2—N3	3.188 (3)	C1—H1	1.02 (2)
K2—O3	3.236 (3)	C2—H2A	0.9600
K2—N2ⁱⁱ	3.2555 (16)	C2—H2B	0.9600
K2—O2ⁱⁱ	3.2676 (15)	C2—H2C	0.9600
K2—O1^vi	3.3410 (18)	O1W—H1A	0.85 (3)
O1—N1	1.292 (2)	O1W—H1B	0.81 (4)
O1—K2^iv	3.3409 (18)

O2ⁱ—K1—O3ⁱⁱ	146.27 (4)	O4—K2—O3	47.84 (5)
O2ⁱ—K1—O1	114.12 (5)	N4—K2—O3	42.26 (5)
O3ⁱⁱ—K1—O1	83.60 (5)	N2^vi—K2—O3	150.02 (4)
O2ⁱ—K1—O4ⁱⁱ	91.75 (4)	N3—K2—O3	23.41 (4)
O3ⁱⁱ—K1—O4ⁱⁱ	54.72 (4)	O1W—K2—N2ⁱⁱ	122.84 (5)
O1—K1—O4ⁱⁱ	108.37 (7)	O3ⁱⁱ—K2—N2ⁱⁱ	65.35 (4)
O2ⁱ—K1—N2ⁱⁱⁱ	74.23 (4)	O2^vi—K2—N2ⁱⁱ	66.62 (4)
O3ⁱⁱ—K1—N2ⁱⁱⁱ	93.11 (5)	O1—K2—N2ⁱⁱ	139.70 (5)
O1—K1—N2ⁱⁱⁱ	168.73 (4)	O4—K2—N2ⁱⁱ	95.33 (4)
O4ⁱⁱ—K1—N2ⁱⁱⁱ	78.00 (7)	N4—K2—N2ⁱⁱ	117.71 (5)
O2ⁱ—K1—O4^iv	84.14 (4)	N2^vi—K2—N2ⁱⁱ	89.70 (5)
O3ⁱⁱ—K1—O4^iv	129.55 (4)	N3—K2—N2ⁱⁱ	116.46 (5)
O1—K1—O4^iv	70.51 (6)	O3—K2—N2ⁱⁱ	95.99 (4)
O4ⁱⁱ—K1—O4^iv	174.69 (4)	O1W—K2—O2ⁱⁱ	142.13 (5)
N2ⁱⁱⁱ—K1—O4^iv	104.01 (7)	O3ⁱⁱ—K2—O2ⁱⁱ	86.10 (4)
O2ⁱ—K1—O1W	139.33 (5)	O2^vi—K2—O2ⁱⁱ	65.49 (5)
O3ⁱⁱ—K1—O1W	73.71 (5)	O1—K2—O2ⁱⁱ	144.35 (5)
O1—K1—O1W	64.13 (6)	O4—K2—O2ⁱⁱ	73.19 (4)
O4ⁱⁱ—K1—O1W	128.36 (4)	N4—K2—O2ⁱⁱ	96.56 (5)
N2ⁱⁱⁱ—K1—O1W	104.61 (6)	N2^vi—K2—O2ⁱⁱ	89.19 (5)
O4^iv—K1—O1W	56.20 (4)	N3—K2—O2ⁱⁱ	100.82 (6)
O2ⁱ—K1—O2	71.83 (3)	O3—K2—O2ⁱⁱ	85.10 (5)
O3ⁱⁱ—K1—O2	102.26 (6)	N2ⁱⁱ—K2—O2ⁱⁱ	22.81 (3)
O1—K1—O2	52.51 (5)	O1W—K2—O1^vi	94.18 (5)
O4ⁱⁱ—K1—O2	80.24 (6)	O3ⁱⁱ—K2—O1^vi	155.00 (5)
N2ⁱⁱⁱ—K1—O2	138.72 (5)	O2^vi—K2—O1^vi	48.18 (4)
O4^iv—K1—O2	95.24 (6)	O1—K2—O1^vi	116.39 (7)
O1W—K1—O2	116.41 (5)	O4—K2—O1^vi	62.60 (5)
O2ⁱ—K1—O2ⁱⁱⁱ	68.50 (3)	N4—K2—O1^vi	69.22 (5)
O3ⁱⁱ—K1—O2ⁱⁱⁱ	110.95 (4)	N2^vi—K2—O1^vi	41.09 (4)
O1—K1—O2ⁱⁱⁱ	149.84 (4)	N3—K2—O1^vi	92.51 (4)
O4ⁱⁱ—K1—O2ⁱⁱⁱ	101.45 (6)	O3—K2—O1^vi	109.14 (4)
N2ⁱⁱⁱ—K1—O2ⁱⁱⁱ	23.99 (4)	N2ⁱⁱ—K2—O1^vi	102.56 (4)
O4^iv—K1—O2ⁱⁱⁱ	80.21 (5)	O2ⁱⁱ—K2—O1^vi	87.34 (4)
O1W—K1—O2ⁱⁱⁱ	93.82 (6)	N1—O1—K1	124.07 (11)
O2—K1—O2ⁱⁱⁱ	140.33 (4)	N1—O1—K2	120.88 (11)
O2ⁱ—K1—K2^iv	57.94 (3)	K1—O1—K2	88.71 (5)
O3ⁱⁱ—K1—K2^iv	140.74 (4)	N1—O1—K2^iv	79.61 (10)
O1—K1—K2^iv	58.81 (4)	K1—O1—K2^iv	75.53 (4)
O4ⁱⁱ—K1—K2^iv	123.54 (4)	K2—O1—K2^iv	159.23 (5)
N2ⁱⁱⁱ—K1—K2^iv	125.95 (3)	N2—N1—O1	125.46 (14)
O4^iv—K1—K2^iv	51.29 (4)	N2—N1—C1	115.81 (15)
O1W—K1—K2^iv	97.03 (4)	O1—N1—C1	118.67 (14)
O2—K1—K2^iv	47.03 (3)	N2—N1—K2^iv	70.45 (10)
O2ⁱⁱⁱ—K1—K2^iv	107.63 (3)	O1—N1—K2^iv	78.15 (11)
O2ⁱ—K1—K1^v	54.55 (4)	C1—N1—K2^iv	128.48 (10)
O3ⁱⁱ—K1—K1^v	97.83 (4)	N1—N2—O2	113.61 (15)
O1—K1—K1^v	93.78 (6)	N1—N2—K1^vii	155.73 (11)
O4ⁱⁱ—K1—K1^v	49.11 (3)	O2—N2—K1^vii	90.42 (11)
N2ⁱⁱⁱ—K1—K1^v	97.35 (6)	N1—N2—K2^iv	87.09 (10)
O4^iv—K1—K1^v	125.58 (3)	O2—N2—K2^iv	61.55 (9)
O1W—K1—K1^v	156.75 (4)	K1^vii—N2—K2^iv	102.44 (7)
O2—K1—K1^v	43.10 (4)	N1—N2—K2ⁱⁱ	89.10 (9)
O2ⁱⁱⁱ—K1—K1^v	109.42 (6)	O2—N2—K2ⁱⁱ	79.12 (9)
K2^iv—K1—K1^v	75.609 (18)	K1^vii—N2—K2ⁱⁱ	99.22 (4)
O2ⁱ—K1—K1ⁱ	50.12 (4)	K2^iv—N2—K2ⁱⁱ	134.70 (5)
O3ⁱⁱ—K1—K1ⁱ	150.08 (4)	N2—O2—K1^v	139.09 (11)
O1—K1—K1ⁱ	113.84 (5)	N2—O2—K2^iv	94.50 (10)
O4ⁱⁱ—K1—K1ⁱ	131.65 (3)	K1^v—O2—K2^iv	119.01 (5)
N2ⁱⁱⁱ—K1—K1ⁱ	64.91 (5)	N2—O2—K1	122.92 (11)
O4^iv—K1—K1ⁱ	47.01 (3)	K1^v—O2—K1	86.79 (4)
O1W—K1—K1ⁱ	91.69 (5)	K2^iv—O2—K1	81.95 (6)
O2—K1—K1ⁱ	107.64 (6)	N2—O2—K1^vii	65.59 (10)
O2ⁱⁱⁱ—K1—K1ⁱ	42.75 (4)	K1^v—O2—K1^vii	82.70 (4)
K2^iv—K1—K1ⁱ	65.54 (4)	K2^iv—O2—K1^vii	104.55 (6)
K1^v—K1—K1ⁱ	104.65 (5)	K1—O2—K1^vii	169.37 (5)
O2ⁱ—K1—H1A	123.7 (6)	N2—O2—K2ⁱⁱ	78.07 (9)
O3ⁱⁱ—K1—H1A	89.8 (6)	K1^v—O2—K2ⁱⁱ	78.76 (4)
O1—K1—H1A	60.5 (6)	K2^iv—O2—K2ⁱⁱ	155.83 (5)
O4ⁱⁱ—K1—H1A	144.5 (6)	K1—O2—K2ⁱⁱ	83.00 (6)
N2ⁱⁱⁱ—K1—H1A	108.9 (6)	K1^vii—O2—K2ⁱⁱ	93.37 (5)
O4^iv—K1—H1A	39.8 (6)	N3—O3—K1ⁱⁱ	122.32 (9)
O1W—K1—H1A	16.7 (6)	N3—O3—K2ⁱⁱ	138.25 (10)
O2—K1—H1A	109.2 (6)	K1ⁱⁱ—O3—K2ⁱⁱ	93.90 (4)
O2ⁱⁱⁱ—K1—H1A	92.3 (6)	N3—O3—K2	76.23 (9)
K2^iv—K1—H1A	81.6 (6)	K1ⁱⁱ—O3—K2	88.35 (5)
K1^v—K1—H1A	152.2 (6)	K2ⁱⁱ—O3—K2	85.70 (4)
K1ⁱ—K1—H1A	79.4 (6)	N4—N3—O3	124.88 (14)
O1W—K2—O3ⁱⁱ	76.74 (5)	N4—N3—C1	119.06 (14)
O1W—K2—O2^vi	87.69 (7)	O3—N3—C1	115.93 (13)
O3ⁱⁱ—K2—O2^vi	107.54 (5)	N4—N3—K2	75.18 (10)
O1W—K2—O1	66.37 (6)	O3—N3—K2	80.36 (10)
O3ⁱⁱ—K2—O1	81.64 (4)	C1—N3—K2	113.47 (10)
O2^vi—K2—O1	150.15 (5)	N3—N4—O4	113.20 (14)
O1W—K2—O4	139.74 (6)	N3—N4—K2	81.38 (10)
O3ⁱⁱ—K2—O4	137.12 (5)	O4—N4—K2	73.04 (10)
O2^vi—K2—O4	97.50 (6)	N4—O4—K1ⁱⁱ	122.08 (10)
O1—K2—O4	93.68 (4)	N4—O4—K1^vi	148.22 (12)
O1W—K2—N4	119.35 (7)	K1ⁱⁱ—O4—K1^vi	83.88 (5)
O3ⁱⁱ—K2—N4	135.54 (5)	N4—O4—K2	82.70 (9)
O2^vi—K2—N4	113.88 (5)	K1ⁱⁱ—O4—K2	90.05 (6)
O1—K2—N4	70.61 (4)	K1^vi—O4—K2	79.02 (5)
O4—K2—N4	24.25 (4)	N1—C1—N3	104.70 (13)
O1W—K2—N2^vi	68.65 (7)	N1—C1—C2	111.39 (17)
O3ⁱⁱ—K2—N2^vi	114.67 (5)	N3—C1—C2	114.27 (16)
O2^vi—K2—N2^vi	23.94 (4)	N1—C1—H1	105.5 (13)
O1—K2—N2^vi	126.32 (5)	N3—C1—H1	109.3 (12)
O4—K2—N2^vi	102.40 (7)	C2—C1—H1	111.2 (12)
N4—K2—N2^vi	109.75 (6)	C1—C2—H2A	109.5
O1W—K2—N3	116.88 (7)	C1—C2—H2B	109.5
O3ⁱⁱ—K2—N3	112.41 (4)	H2A—C2—H2B	109.5
O2^vi—K2—N3	136.67 (4)	C1—C2—H2C	109.5
O1—K2—N3	54.83 (4)	H2A—C2—H2C	109.5
O4—K2—N3	40.46 (4)	H2B—C2—H2C	109.5
N4—K2—N3	23.44 (4)	K2—O1W—K1	88.05 (6)
N2^vi—K2—N3	132.37 (5)	K2—O1W—H1A	122 (2)
O1W—K2—O3	129.12 (6)	K1—O1W—H1A	69 (2)
O3ⁱⁱ—K2—O3	94.30 (4)	K2—O1W—H1B	134 (2)
O2^vi—K2—O3	141.23 (4)	K1—O1W—H1B	113 (2)
O1—K2—O3	62.77 (4)	H1A—O1W—H1B	103 (3)

O1—N1—N2—O2	−1.5 (2)	O1—N1—C1—C2	62.7 (2)
O2—N2—N1—C1	−178.69 (14)	O1—N1—C1—N3	−61.3 (2)
N2—N1—C1—C2	−119.95 (19)	O3—N3—C1—N1	−54.37 (19)
N2—N1—C1—N3	116.04 (16)	O3—N3—C1—C2	−176.51 (18)
N1—C1—N3—O3	−54.37 (19)	O3—N3—N4—O4	−0.6 (2)
C1—N3—N4—O4	−176.22 (14)

Symmetry codes: (i) y+1, z, x; (ii) −x+1, −y, −z+1; (iii) z+1, x, y+1; (iv) −y+1, −z+1, −x+1; (v) z, x−1, y; (vi) −z+1, −x+1, −y+1; (vii) y, z−1, x−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4^iv	0.85 (3)	1.95 (3)	2.773 (2)	163 (3)
O1W—H1B···O3^viii	0.81 (4)	2.10 (4)	2.908 (4)	175 (3)

Symmetry codes: (iv) −y+1, −z+1, −x+1; (viii) x+1, y+1, z+1.

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