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The asymmetric unit of the title compound, C9H8NO+·C6H3N2O4·2H2O, contains two independent cations, two anions and four water mol­ecules of solvation. A three-dimensional framework structure is formed through extensive hydrogen-bonding involving most donor and acceptor species. Significant aromatic C—H...O and cation–cation π–π inter­actions are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042322/fl2064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042322/fl2064Isup2.hkl
Contains datablock I

CCDC reference: 627656

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.103
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT417_ALERT_2_C Short Inter D-H..H-D H8A .. H22W .. 2.14 Ang. PLAT417_ALERT_2_C Short Inter D-H..H-D H8B .. H12W .. 2.12 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

8-hydroxyquinolinium 3-carboxypyrazine-2-carboxylate dihydrate top
Crystal data top
C9H8NO+·C6H3N2O4·2H2OZ = 4
Mr = 349.30F(000) = 728
Triclinic, P1Dx = 1.530 Mg m3
Hall symbol: -P 1Melting point = 442.6–445.1 K
a = 6.8754 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.0387 (15) ÅCell parameters from 2861 reflections
c = 19.338 (2) Åθ = 2.8–27.4°
α = 86.138 (2)°µ = 0.12 mm1
β = 80.977 (2)°T = 130 K
γ = 73.673 (2)°Block, yellow
V = 1516.6 (3) Å30.40 × 0.40 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5281 independent reflections
Radiation source: sealed tube4475 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 78
Tmin = 0.93, Tmax = 0.97k = 1314
8060 measured reflectionsl = 1522
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.4013P]
where P = (Fo2 + 2Fc2)/3
5281 reflections(Δ/σ)max < 0.001
508 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O8A0.95861 (19)0.22051 (10)0.09507 (7)0.0238 (4)
N1A0.8933 (2)0.12725 (13)0.03273 (7)0.0187 (4)
C2A0.8720 (3)0.08558 (15)0.09719 (9)0.0209 (5)
C3A0.7584 (3)0.02884 (15)0.10815 (9)0.0222 (5)
C4A0.6686 (3)0.09746 (15)0.05210 (9)0.0214 (5)
C5A0.5992 (3)0.11959 (15)0.07757 (9)0.0219 (5)
C6A0.6243 (3)0.06960 (15)0.14248 (9)0.0229 (6)
C7A0.7426 (3)0.04522 (15)0.15056 (9)0.0229 (6)
C8A0.8360 (3)0.11150 (14)0.09310 (9)0.0197 (5)
C9A0.8064 (2)0.06232 (14)0.02584 (9)0.0184 (5)
C10A0.6892 (2)0.05379 (14)0.01699 (9)0.0191 (5)
O8B0.5119 (2)0.26474 (11)0.43384 (7)0.0289 (4)
N1B0.3415 (2)0.34458 (13)0.56217 (7)0.0211 (5)
C2B0.2570 (3)0.37760 (16)0.62674 (9)0.0238 (6)
C3B0.1388 (3)0.49152 (16)0.63874 (10)0.0248 (6)
C4B0.1154 (3)0.56968 (15)0.58402 (10)0.0238 (6)
C5B0.1894 (3)0.61195 (15)0.45628 (10)0.0252 (6)
C6B0.2788 (3)0.57123 (15)0.39144 (10)0.0257 (6)
C7B0.3882 (3)0.45410 (15)0.38126 (10)0.0243 (6)
C8B0.4086 (3)0.37736 (15)0.43729 (9)0.0208 (5)
C9B0.3184 (2)0.41853 (14)0.50507 (9)0.0210 (5)
C10B0.2053 (3)0.53570 (14)0.51521 (9)0.0195 (5)
O21C0.15999 (19)0.16791 (10)0.30535 (6)0.0260 (4)
O22C0.48654 (18)0.16222 (10)0.28542 (6)0.0228 (4)
O31C0.0193 (2)0.23422 (10)0.30989 (7)0.0308 (4)
O32C0.1598 (3)0.07037 (11)0.25293 (7)0.0419 (5)
N1C0.3323 (2)0.10391 (12)0.43700 (7)0.0200 (4)
N4C0.1298 (2)0.13360 (12)0.43093 (7)0.0203 (4)
C2C0.2662 (2)0.05207 (14)0.37784 (9)0.0174 (5)
C3C0.1692 (2)0.06694 (14)0.37473 (9)0.0178 (5)
C5C0.1892 (3)0.08018 (15)0.48977 (9)0.0218 (5)
C6C0.2909 (3)0.03680 (15)0.49264 (9)0.0207 (5)
C21C0.3050 (3)0.13261 (14)0.31695 (9)0.0188 (5)
C31C0.1148 (3)0.12434 (14)0.30599 (9)0.0208 (5)
O21D0.63743 (19)0.32364 (10)0.19878 (6)0.0266 (4)
O22D0.96231 (19)0.33190 (10)0.18958 (6)0.0258 (4)
O31D0.5377 (2)0.72930 (10)0.16967 (6)0.0264 (4)
O32D0.6311 (2)0.56367 (11)0.23062 (7)0.0367 (5)
N1D0.8259 (2)0.37920 (12)0.04551 (7)0.0205 (5)
N4D0.6458 (2)0.61955 (12)0.04781 (7)0.0211 (5)
C2D0.7591 (2)0.43573 (14)0.10623 (9)0.0179 (5)
C3D0.6722 (2)0.55580 (14)0.10693 (9)0.0180 (5)
C5D0.7071 (3)0.56204 (15)0.01175 (9)0.0231 (5)
C6D0.7982 (3)0.44355 (15)0.01319 (9)0.0221 (5)
C21D0.7856 (3)0.35895 (14)0.17180 (9)0.0199 (5)
C31D0.6109 (3)0.61707 (14)0.17578 (9)0.0196 (5)
O1W0.5667 (2)0.17934 (13)0.31231 (7)0.0309 (5)
O2W1.0373 (2)0.30260 (13)0.21839 (7)0.0284 (4)
O3W0.2346 (2)0.47001 (12)0.18710 (7)0.0323 (5)
O4W0.7482 (2)0.05043 (12)0.33800 (7)0.0281 (4)
H1A0.970 (3)0.1983 (18)0.0256 (10)0.027 (5)*
H2A0.934000.133600.136100.0250*
H3A0.743900.058600.154400.0270*
H4A0.591700.175100.059500.0260*
H5A0.521700.198000.073200.0260*
H6A0.560400.113500.182900.0270*
H7A0.758200.077400.196200.0270*
H8A0.985 (3)0.2451 (19)0.1394 (12)0.041 (6)*
H1B0.429 (3)0.2701 (19)0.5531 (11)0.037 (6)*
H2B0.276900.323600.664900.0290*
H3B0.075100.514500.684700.0300*
H4B0.037900.647600.592300.0290*
H5B0.116700.691300.461800.0300*
H6B0.267100.623200.352100.0310*
H7B0.448000.428100.335500.0290*
H8B0.532 (4)0.235 (2)0.3910 (14)0.057 (7)*
H5C0.161000.123700.531100.0260*
H6C0.332500.070400.535700.0250*
H31C0.001 (4)0.268 (2)0.2680 (14)0.072 (8)*
H5D0.687800.603700.054800.0280*
H6D0.842200.407000.057100.0270*
H31D0.521 (4)0.759 (2)0.2090 (14)0.040 (8)*
H11W0.616 (4)0.218 (2)0.2751 (14)0.062 (8)*
H12W0.648 (4)0.105 (3)0.3151 (14)0.068 (9)*
H21W1.102 (4)0.268 (2)0.2426 (13)0.049 (7)*
H22W1.112 (4)0.374 (2)0.2136 (13)0.058 (8)*
H31W0.154 (4)0.427 (2)0.1901 (13)0.059 (8)*
H32W0.357 (4)0.425 (2)0.1939 (12)0.051 (7)*
H41W0.679 (4)0.089 (2)0.3201 (13)0.053 (8)*
H42W0.883 (4)0.090 (2)0.3266 (13)0.053 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O8A0.0294 (7)0.0192 (6)0.0183 (7)0.0011 (5)0.0052 (5)0.0011 (5)
N1A0.0189 (7)0.0175 (8)0.0180 (8)0.0020 (6)0.0029 (6)0.0019 (6)
C2A0.0220 (9)0.0225 (9)0.0182 (9)0.0059 (7)0.0033 (7)0.0014 (7)
C3A0.0237 (9)0.0226 (9)0.0201 (9)0.0062 (7)0.0045 (7)0.0023 (7)
C4A0.0195 (9)0.0186 (9)0.0266 (10)0.0051 (7)0.0059 (7)0.0017 (7)
C5A0.0195 (9)0.0170 (9)0.0273 (10)0.0021 (7)0.0016 (7)0.0039 (7)
C6A0.0221 (9)0.0255 (10)0.0202 (10)0.0054 (7)0.0009 (7)0.0082 (7)
C7A0.0241 (10)0.0258 (10)0.0187 (9)0.0068 (8)0.0027 (7)0.0002 (7)
C8A0.0187 (9)0.0193 (9)0.0205 (9)0.0047 (7)0.0025 (7)0.0004 (7)
C9A0.0153 (8)0.0198 (9)0.0204 (9)0.0054 (7)0.0012 (7)0.0030 (7)
C10A0.0166 (9)0.0189 (9)0.0226 (10)0.0064 (7)0.0024 (7)0.0011 (7)
O8B0.0394 (8)0.0201 (7)0.0193 (7)0.0040 (6)0.0027 (6)0.0011 (5)
N1B0.0222 (8)0.0184 (8)0.0208 (8)0.0022 (6)0.0039 (6)0.0008 (6)
C2B0.0247 (9)0.0273 (10)0.0190 (10)0.0061 (8)0.0034 (7)0.0012 (7)
C3B0.0212 (9)0.0292 (10)0.0225 (10)0.0038 (8)0.0019 (7)0.0067 (8)
C4B0.0202 (9)0.0212 (9)0.0303 (11)0.0030 (7)0.0063 (8)0.0072 (8)
C5B0.0254 (10)0.0179 (9)0.0332 (11)0.0048 (7)0.0095 (8)0.0013 (8)
C6B0.0277 (10)0.0235 (10)0.0280 (11)0.0084 (8)0.0106 (8)0.0062 (8)
C7B0.0250 (10)0.0279 (10)0.0211 (10)0.0080 (8)0.0054 (7)0.0001 (8)
C8B0.0200 (9)0.0206 (9)0.0211 (9)0.0030 (7)0.0044 (7)0.0029 (7)
C9B0.0185 (9)0.0193 (9)0.0268 (10)0.0055 (7)0.0067 (7)0.0024 (7)
C10B0.0183 (9)0.0194 (9)0.0215 (9)0.0051 (7)0.0056 (7)0.0005 (7)
O21C0.0254 (7)0.0242 (7)0.0290 (7)0.0057 (5)0.0053 (5)0.0071 (5)
O22C0.0230 (7)0.0228 (7)0.0198 (6)0.0025 (5)0.0006 (5)0.0054 (5)
O31C0.0480 (8)0.0173 (7)0.0203 (7)0.0059 (6)0.0114 (6)0.0015 (5)
O32C0.0757 (11)0.0235 (7)0.0167 (7)0.0061 (7)0.0120 (7)0.0046 (6)
N1C0.0214 (8)0.0186 (7)0.0181 (8)0.0033 (6)0.0014 (6)0.0008 (6)
N4C0.0230 (8)0.0189 (7)0.0180 (8)0.0039 (6)0.0025 (6)0.0030 (6)
C2C0.0158 (8)0.0186 (9)0.0175 (9)0.0049 (7)0.0015 (7)0.0007 (7)
C3C0.0173 (8)0.0175 (8)0.0178 (9)0.0033 (7)0.0022 (7)0.0014 (7)
C5C0.0258 (10)0.0222 (9)0.0168 (9)0.0049 (7)0.0033 (7)0.0030 (7)
C6C0.0230 (9)0.0215 (9)0.0161 (9)0.0033 (7)0.0041 (7)0.0016 (7)
C21C0.0247 (10)0.0133 (8)0.0164 (9)0.0013 (7)0.0058 (7)0.0026 (7)
C31C0.0247 (9)0.0163 (9)0.0196 (9)0.0022 (7)0.0032 (7)0.0018 (7)
O21D0.0312 (7)0.0241 (7)0.0240 (7)0.0085 (6)0.0027 (6)0.0032 (5)
O22D0.0270 (7)0.0244 (7)0.0238 (7)0.0019 (5)0.0089 (5)0.0042 (5)
O31D0.0392 (8)0.0177 (6)0.0178 (7)0.0002 (6)0.0036 (6)0.0022 (5)
O32D0.0664 (10)0.0208 (7)0.0191 (7)0.0042 (7)0.0096 (7)0.0003 (6)
N1D0.0216 (8)0.0192 (8)0.0193 (8)0.0027 (6)0.0037 (6)0.0012 (6)
N4D0.0251 (8)0.0197 (8)0.0166 (8)0.0029 (6)0.0040 (6)0.0001 (6)
C2D0.0168 (8)0.0186 (9)0.0179 (9)0.0037 (7)0.0030 (7)0.0020 (7)
C3D0.0177 (9)0.0187 (9)0.0173 (9)0.0042 (7)0.0035 (7)0.0004 (7)
C5D0.0275 (10)0.0227 (9)0.0161 (9)0.0021 (7)0.0040 (7)0.0012 (7)
C6D0.0245 (9)0.0224 (9)0.0173 (9)0.0027 (7)0.0030 (7)0.0011 (7)
C21D0.0267 (10)0.0125 (8)0.0185 (9)0.0012 (7)0.0036 (7)0.0047 (7)
C31D0.0213 (9)0.0166 (9)0.0199 (10)0.0026 (7)0.0045 (7)0.0006 (7)
O1W0.0438 (9)0.0249 (8)0.0206 (7)0.0069 (7)0.0011 (6)0.0007 (6)
O2W0.0366 (8)0.0240 (7)0.0260 (8)0.0061 (6)0.0130 (6)0.0006 (6)
O3W0.0315 (8)0.0270 (8)0.0381 (9)0.0061 (7)0.0073 (6)0.0010 (6)
O4W0.0255 (8)0.0296 (7)0.0279 (8)0.0045 (6)0.0030 (6)0.0069 (6)
Geometric parameters (Å, º) top
O8A—C8A1.348 (2)C5A—C6A1.369 (2)
O8A—H8A0.92 (2)C5A—C10A1.416 (2)
O8B—C8B1.343 (2)C6A—C7A1.406 (3)
O8B—H8B0.93 (3)C7A—C8A1.375 (2)
O21C—C21C1.243 (2)C8A—C9A1.413 (2)
O22C—C21C1.264 (2)C9A—C10A1.418 (2)
O31C—C31C1.302 (2)C2A—H2A0.9500
O32C—C31C1.203 (2)C3A—H3A0.9500
O31C—H31C0.90 (3)C4A—H4A0.9500
O21D—C21D1.240 (2)C5A—H5A0.9500
O22D—C21D1.263 (2)C6A—H6A0.9500
O31D—C31D1.307 (2)C7A—H7A0.9500
O32D—C31D1.209 (2)C2B—C3B1.397 (3)
O31D—H31D0.84 (3)C3B—C4B1.366 (3)
O1W—H12W0.92 (3)C4B—C10B1.412 (3)
O1W—H11W0.90 (3)C5B—C10B1.412 (3)
N1A—C9A1.377 (2)C5B—C6B1.365 (3)
N1A—C2A1.326 (2)C6B—C7B1.410 (2)
N1A—H1A0.88 (2)C7B—C8B1.374 (3)
O2W—H22W0.87 (2)C8B—C9B1.417 (2)
O2W—H21W0.89 (3)C9B—C10B1.416 (2)
N1B—C2B1.328 (2)C2B—H2B0.9500
N1B—C9B1.371 (2)C3B—H3B0.9500
N1B—H1B0.94 (2)C4B—H4B0.9500
O3W—H31W0.85 (3)C5B—H5B0.9500
O3W—H32W0.89 (3)C6B—H6B0.9500
N1C—C2C1.346 (2)C7B—H7B0.9500
N1C—C6C1.335 (2)C2C—C21C1.519 (2)
N4C—C5C1.332 (2)C2C—C3C1.402 (2)
N4C—C3C1.342 (2)C3C—C31C1.507 (2)
O4W—H41W0.87 (3)C5C—C6C1.387 (2)
O4W—H42W0.92 (3)C5C—H5C0.9500
N1D—C6D1.338 (2)C6C—H6C0.9500
N1D—C2D1.347 (2)C2D—C21D1.522 (2)
N4D—C5D1.332 (2)C2D—C3D1.400 (2)
N4D—C3D1.341 (2)C3D—C31D1.509 (2)
C2A—C3A1.400 (3)C5D—C6D1.388 (2)
C3A—C4A1.365 (2)C5D—H5D0.9500
C4A—C10A1.416 (2)C6D—H6D0.9500
O1W···O21D2.7750 (19)C2A···O32Cix3.043 (2)
O1W···O4W2.743 (2)C2B···C7Bx3.563 (3)
O1W···O8B2.5597 (19)C2B···O32Dx3.152 (2)
O1W···C31C3.375 (3)C2B···O22Civ3.239 (2)
O1W···C3C3.403 (2)C2B···C6Bx3.378 (3)
O1W···C8B3.347 (2)C2C···O4W3.288 (2)
O2W···C8A3.404 (2)C3A···C6Aix3.343 (3)
O2W···O8A2.5967 (19)C3A···C5Aix3.385 (3)
O2W···O21Ci2.7839 (19)C3A···C8Av3.272 (3)
O3W···O21D2.868 (2)C3A···C7Av3.458 (3)
O3W···O22Dii2.825 (2)C3A···O31Diii3.316 (2)
O3W···C5Diii3.387 (2)C3A···O32Cix3.027 (2)
O4W···O22C2.8637 (19)C3B···C6Bvii3.311 (3)
O4W···C5Civ3.407 (2)C3B···O31Cvii3.340 (2)
O4W···O21Ci2.779 (2)C3B···C7Bx3.453 (3)
O4W···C2C3.288 (2)C3B···O32Dx3.125 (2)
O4W···O1W2.743 (2)C3B···C7Bvii3.575 (3)
O8A···C4Av3.280 (2)C3C···O1W3.403 (2)
O8A···O31Dvi3.221 (2)C4A···O31Diii3.200 (2)
O8A···C6Dv3.119 (2)C4A···C10Aix3.414 (3)
O8A···N1A2.6946 (19)C4A···C8Av3.423 (3)
O8A···O2W2.5967 (19)C4A···O8Av3.280 (2)
O8B···N1Civ3.1869 (19)C4A···C9Aix3.366 (3)
O8B···O1W2.5597 (19)C4B···C6Bvii3.539 (3)
O8B···C6Civ3.062 (2)C4B···C7Bvii3.511 (3)
O8B···N1B2.6891 (19)C4B···C8Bx3.464 (3)
O21C···C6Bvi3.403 (2)C4B···C7Bx3.511 (3)
O21C···O2Wii2.7839 (19)C4B···C8Bvii3.563 (3)
O21C···O32C2.9771 (18)C4B···O31Cvii3.077 (2)
O21C···N1C3.1941 (19)C5A···C3Aix3.385 (3)
O21C···O4Wii2.779 (2)C5A···C2Aix3.339 (3)
O21D···C6A3.344 (2)C5B···C10Bvii3.597 (3)
O21D···O1W2.7750 (19)C5B···N1Bx3.371 (3)
O21D···N1D3.1507 (18)C5B···C9Bx3.493 (3)
O21D···O32D2.9819 (18)C5B···C9Bvii3.570 (3)
O21D···O3W2.868 (2)C5C···C6Cxii3.446 (3)
O22C···C2Biv3.239 (2)C5C···O4Wiv3.407 (2)
O22C···C7A3.368 (2)C5C···C6Civ3.532 (3)
O22C···N1C3.0155 (18)C5D···N1Dxi3.434 (3)
O22C···C31Dvi3.347 (2)C5D···C5Diii3.527 (3)
O22C···O31Dvi2.5939 (17)C5D···C6Diii3.451 (3)
O22C···O4W2.8637 (19)C5D···C6Dxi3.491 (3)
O22C···O32C3.155 (2)C5D···O3Wiii3.387 (2)
O22D···N1D3.0449 (18)C6A···O21D3.344 (2)
O22D···C31Ci3.305 (2)C6A···C2Av3.493 (3)
O22D···O32D3.1241 (18)C6A···C3Aix3.343 (3)
O22D···O31Ci2.5705 (18)C6B···C4Bvii3.539 (3)
O22D···C2Av3.385 (2)C6B···C3Bvii3.311 (3)
O22D···O3Wi2.825 (2)C6B···N1Bx3.315 (3)
O31C···O22Dii2.5705 (18)C6B···C2Bx3.378 (3)
O31C···C3Bvii3.340 (2)C6B···O21Cviii3.403 (2)
O31C···C4Bvii3.077 (2)C6C···C6Civ3.295 (3)
O31C···N4C2.6799 (19)C6C···C5Civ3.532 (3)
O31C···C21Dii3.379 (2)C6C···O8Biv3.062 (2)
O31D···C8Aviii3.309 (2)C6C···C5Cxii3.446 (3)
O31D···N4D2.6776 (18)C6D···C5Dxi3.491 (3)
O31D···C3Aiii3.316 (2)C6D···C5Diii3.451 (3)
O31D···C7Aviii3.368 (2)C6D···C6Dxi3.531 (3)
O31D···C4Aiii3.200 (2)C6D···O8Av3.119 (2)
O31D···C21Cviii3.339 (2)C7A···O22C3.368 (2)
O31D···O22Cviii2.5939 (17)C7A···C3Av3.458 (3)
O31D···O8Aviii3.221 (2)C7A···C2Av3.440 (3)
O32C···O21C2.9771 (18)C7A···O31Dvi3.368 (2)
O32C···C3Aix3.027 (2)C7B···C4Bvii3.511 (3)
O32C···C21C2.666 (2)C7B···C4Bx3.511 (3)
O32C···O22C3.155 (2)C7B···C3Bvii3.575 (3)
O32C···C2Aix3.043 (2)C7B···C2Bx3.563 (3)
O32D···O22D3.1241 (18)C7B···C3Bx3.453 (3)
O32D···O21D2.9819 (18)C8A···C4Av3.423 (3)
O32D···C21D2.650 (2)C8A···O31Dvi3.309 (2)
O32D···C3Bx3.125 (2)C8A···O2W3.404 (2)
O32D···C2Bx3.152 (2)C8A···C2Av3.524 (3)
N1A···C10Av3.294 (2)C8A···C3Av3.272 (3)
N1A···O8A2.6946 (19)C8B···O1W3.347 (2)
N1A···N1Dv3.106 (2)C8B···C10Bx3.383 (3)
N1B···N1Civ3.127 (2)C8B···C4Bx3.464 (3)
N1B···C5Bx3.371 (3)C8B···C4Bvii3.563 (3)
N1B···O8B2.6891 (19)C9A···C9Av3.398 (2)
N1B···C6Bx3.315 (3)C9A···C10Av3.466 (2)
N1C···N1Biv3.127 (2)C9A···C4Aix3.366 (3)
N1C···O8Biv3.1869 (19)C9B···C10Bvii3.567 (3)
N1C···O22C3.0155 (18)C9B···C5Bvii3.570 (3)
N1C···N4C2.810 (2)C9B···C9Bx3.560 (2)
N1C···O21C3.1941 (19)C9B···C5Bx3.493 (3)
N1D···O22D3.0449 (18)C9B···C10Bx3.430 (3)
N1D···O21D3.1507 (18)C10A···N1Av3.294 (2)
N1D···N1Av3.106 (2)C10A···C10Aix3.380 (2)
N1D···N4D2.810 (2)C10A···C4Aix3.414 (3)
N1D···C5Dxi3.434 (3)C10A···C9Av3.466 (2)
N4C···N1C2.810 (2)C10B···C10Bvii3.318 (3)
N4C···O31C2.6799 (19)C10B···C8Bx3.383 (3)
N4D···N1D2.810 (2)C10B···C9Bx3.430 (3)
N4D···O31D2.6776 (18)C10B···C5Bvii3.597 (3)
N1C···H1Biv2.22 (2)C10B···C9Bvii3.567 (3)
N1D···H1Av2.26 (2)C21C···O32C2.666 (2)
N4C···H4Bvii2.6000C21C···O31Dvi3.339 (2)
N4D···H4Aiii2.5500C21D···O31Ci3.379 (2)
C2A···C5Aix3.339 (3)C21D···O32D2.650 (2)
C2A···C8Av3.524 (3)C31C···O1W3.375 (3)
C2A···C6Av3.493 (3)C31C···O22Dii3.305 (2)
C2A···O22Dv3.385 (2)C31D···O22Cviii3.347 (2)
C2A···C7Av3.440 (3)
C8A—O8A—H8A112.6 (14)N1B—C9B—C8B119.90 (15)
C8B—O8B—H8B114.4 (16)C8B—C9B—C10B121.09 (15)
C31C—O31C—H31C112.9 (15)N1B—C9B—C10B119.01 (15)
C31D—O31D—H31D109.4 (16)C4B—C10B—C9B117.87 (15)
H11W—O1W—H12W111 (2)C4B—C10B—C5B123.72 (16)
C2A—N1A—C9A122.66 (15)C5B—C10B—C9B118.42 (16)
C9A—N1A—H1A116.6 (12)N1B—C2B—H2B120.00
C2A—N1A—H1A120.7 (12)C3B—C2B—H2B120.00
H21W—O2W—H22W107 (2)C2B—C3B—H3B120.00
C2B—N1B—C9B122.59 (15)C4B—C3B—H3B120.00
C2B—N1B—H1B121.8 (13)C10B—C4B—H4B120.00
C9B—N1B—H1B115.5 (13)C3B—C4B—H4B120.00
H31W—O3W—H32W107 (2)C6B—C5B—H5B120.00
C2C—N1C—C6C116.18 (14)C10B—C5B—H5B120.00
C3C—N4C—C5C116.10 (14)C5B—C6B—H6B119.00
H41W—O4W—H42W106 (2)C7B—C6B—H6B119.00
C2D—N1D—C6D116.29 (14)C8B—C7B—H7B120.00
C3D—N4D—C5D116.12 (14)C6B—C7B—H7B120.00
N1A—C2A—C3A120.33 (16)N1C—C2C—C21C114.64 (14)
C2A—C3A—C4A119.70 (16)C3C—C2C—C21C124.18 (15)
C3A—C4A—C10A120.52 (16)N1C—C2C—C3C121.18 (15)
C6A—C5A—C10A119.66 (16)N4C—C3C—C31C118.15 (14)
C5A—C6A—C7A121.47 (16)C2C—C3C—C31C119.83 (15)
C6A—C7A—C8A120.77 (16)N4C—C3C—C2C121.97 (15)
C7A—C8A—C9A118.43 (15)N4C—C5C—C6C122.19 (16)
O8A—C8A—C7A125.39 (16)N1C—C6C—C5C122.28 (16)
O8A—C8A—C9A116.17 (15)O21C—C21C—O22C126.34 (16)
N1A—C9A—C10A118.75 (15)O22C—C21C—C2C116.00 (16)
C8A—C9A—C10A121.31 (15)O21C—C21C—C2C117.53 (16)
N1A—C9A—C8A119.94 (15)O31C—C31C—C3C114.38 (15)
C4A—C10A—C5A123.63 (15)O32C—C31C—C3C120.99 (15)
C5A—C10A—C9A118.33 (15)O31C—C31C—O32C124.62 (17)
C4A—C10A—C9A118.04 (15)C6C—C5C—H5C119.00
C3A—C2A—H2A120.00N4C—C5C—H5C119.00
N1A—C2A—H2A120.00N1C—C6C—H6C119.00
C2A—C3A—H3A120.00C5C—C6C—H6C119.00
C4A—C3A—H3A120.00C3D—C2D—C21D124.09 (15)
C3A—C4A—H4A120.00N1D—C2D—C21D114.73 (14)
C10A—C4A—H4A120.00N1D—C2D—C3D121.18 (15)
C6A—C5A—H5A120.00N4D—C3D—C2D122.03 (15)
C10A—C5A—H5A120.00N4D—C3D—C31D118.29 (14)
C5A—C6A—H6A119.00C2D—C3D—C31D119.66 (15)
C7A—C6A—H6A119.00N4D—C5D—C6D122.37 (16)
C6A—C7A—H7A120.00N1D—C6D—C5D121.96 (16)
C8A—C7A—H7A120.00O22D—C21D—C2D115.54 (16)
N1B—C2B—C3B120.20 (16)O21D—C21D—C2D116.96 (17)
C2B—C3B—C4B119.67 (17)O21D—C21D—O22D127.30 (16)
C3B—C4B—C10B120.60 (16)O31D—C31D—O32D124.94 (16)
C6B—C5B—C10B119.78 (16)O31D—C31D—C3D114.10 (14)
C5B—C6B—C7B121.73 (17)O32D—C31D—C3D120.96 (15)
C6B—C7B—C8B120.29 (17)C6D—C5D—H5D119.00
O8B—C8B—C7B125.32 (16)N4D—C5D—H5D119.00
O8B—C8B—C9B116.00 (15)N1D—C6D—H6D119.00
C7B—C8B—C9B118.67 (16)C5D—C6D—H6D119.00
C9A—N1A—C2A—C3A0.3 (3)C6B—C5B—C10B—C4B179.0 (2)
C2A—N1A—C9A—C8A179.55 (18)C6B—C5B—C10B—C9B1.3 (3)
C2A—N1A—C9A—C10A0.1 (2)C10B—C5B—C6B—C7B0.1 (3)
C9B—N1B—C2B—C3B0.1 (3)C5B—C6B—C7B—C8B0.4 (3)
C2B—N1B—C9B—C8B178.57 (18)C6B—C7B—C8B—C9B0.2 (3)
C2B—N1B—C9B—C10B1.9 (3)C6B—C7B—C8B—O8B178.9 (2)
C6C—N1C—C2C—C3C3.2 (2)C7B—C8B—C9B—N1B178.09 (17)
C6C—N1C—C2C—C21C176.56 (16)C7B—C8B—C9B—C10B1.4 (3)
C2C—N1C—C6C—C5C1.2 (3)O8B—C8B—C9B—C10B179.85 (17)
C3C—N4C—C5C—C6C1.7 (3)O8B—C8B—C9B—N1B0.7 (3)
C5C—N4C—C3C—C31C176.92 (17)N1B—C9B—C10B—C5B177.59 (17)
C5C—N4C—C3C—C2C0.3 (2)N1B—C9B—C10B—C4B2.1 (3)
C2D—N1D—C6D—C5D0.4 (3)C8B—C9B—C10B—C5B1.9 (3)
C6D—N1D—C2D—C21D177.68 (16)C8B—C9B—C10B—C4B178.37 (18)
C6D—N1D—C2D—C3D2.1 (2)N1C—C2C—C21C—O22C76.80 (19)
C5D—N4D—C3D—C31D178.30 (17)N1C—C2C—C21C—O21C99.36 (18)
C5D—N4D—C3D—C2D0.0 (2)N1C—C2C—C3C—N4C2.9 (2)
C3D—N4D—C5D—C6D1.7 (3)N1C—C2C—C3C—C31C174.29 (15)
N1A—C2A—C3A—C4A0.3 (3)C21C—C2C—C3C—N4C176.83 (16)
C2A—C3A—C4A—C10A0.1 (3)C21C—C2C—C3C—C31C6.0 (2)
C3A—C4A—C10A—C5A179.52 (19)C3C—C2C—C21C—O21C80.4 (2)
C3A—C4A—C10A—C9A0.4 (3)C3C—C2C—C21C—O22C103.44 (19)
C10A—C5A—C6A—C7A1.8 (3)N4C—C3C—C31C—O31C4.8 (2)
C6A—C5A—C10A—C9A1.1 (3)C2C—C3C—C31C—O32C2.6 (3)
C6A—C5A—C10A—C4A178.88 (19)N4C—C3C—C31C—O32C174.67 (19)
C5A—C6A—C7A—C8A0.5 (3)C2C—C3C—C31C—O31C177.85 (16)
C6A—C7A—C8A—C9A1.4 (3)N4C—C5C—C6C—N1C1.3 (3)
C6A—C7A—C8A—O8A177.28 (19)N1D—C2D—C3D—N4D2.0 (2)
O8A—C8A—C9A—N1A2.9 (3)N1D—C2D—C3D—C31D176.30 (15)
C7A—C8A—C9A—C10A2.1 (3)C21D—C2D—C3D—N4D177.78 (16)
C7A—C8A—C9A—N1A178.32 (17)C21D—C2D—C3D—C31D3.9 (2)
O8A—C8A—C9A—C10A176.72 (15)N1D—C2D—C21D—O21D94.22 (18)
N1A—C9A—C10A—C5A179.54 (15)N1D—C2D—C21D—O22D80.96 (18)
N1A—C9A—C10A—C4A0.4 (2)C3D—C2D—C21D—O21D85.6 (2)
C8A—C9A—C10A—C4A179.18 (17)C3D—C2D—C21D—O22D99.27 (19)
C8A—C9A—C10A—C5A0.9 (2)N4D—C3D—C31D—O31D0.4 (2)
N1B—C2B—C3B—C4B1.9 (3)N4D—C3D—C31D—O32D179.85 (17)
C2B—C3B—C4B—C10B1.6 (3)C2D—C3D—C31D—O31D177.93 (15)
C3B—C4B—C10B—C5B179.3 (2)C2D—C3D—C31D—O32D1.8 (3)
C3B—C4B—C10B—C9B0.4 (3)N4D—C5D—C6D—N1D1.5 (3)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+1, y, z+1; (v) x+2, y, z; (vi) x, y1, z; (vii) x, y+1, z+1; (viii) x, y+1, z; (ix) x+1, y, z; (x) x+1, y+1, z+1; (xi) x+2, y+1, z; (xii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O8A0.88 (2)2.322 (19)2.6946 (19)105.3 (15)
N1A—H1A···N1Dv0.88 (2)2.26 (2)3.106 (2)161.4 (17)
N1B—H1B···O8B0.94 (2)2.29 (2)2.6891 (19)105.0 (15)
N1B—H1B···N1Civ0.94 (2)2.22 (2)3.127 (2)161.8 (18)
O8A—H8A···O2W0.92 (2)1.68 (2)2.5967 (19)175 (2)
O8B—H8B···O1W0.90 (3)1.66 (3)2.5597 (19)179 (4)
O31C—H31C···O22Dii0.90 (3)1.68 (3)2.5705 (18)180 (4)
O31D—H31D···O22Cviii0.84 (3)1.76 (3)2.5939 (17)173 (2)
O1W—H11W···O21D0.90 (3)1.90 (3)2.7750 (19)163 (3)
O1W—H12W···O4W0.92 (3)1.85 (3)2.743 (2)164 (3)
O2W—H21W···O21Ci0.89 (3)1.92 (2)2.7839 (19)163 (2)
O2W—H22W···O3Wxiii0.87 (3)1.90 (2)2.753 (2)166 (3)
O3W—H31W···O22Dii0.85 (3)1.98 (3)2.825 (2)176 (2)
O3W—H32W···O21D0.89 (3)1.98 (3)2.868 (2)174 (2)
O4W—H41W···O22C0.87 (3)2.00 (3)2.8637 (19)172 (2)
O4W—H42W···O21Ci0.92 (3)1.87 (3)2.779 (2)178.2 (12)
C2A—H2A···O22Dv0.952.533.385 (2)149
C2A—H2A···O32Cix0.952.463.043 (2)120
C2B—H2B···O22Civ0.952.413.239 (2)146
C3A—H3A···O32Cix0.952.433.027 (2)121
C4A—H4A···O31Diii0.952.523.200 (2)129
C4A—H4A···N4Diii0.952.553.482 (2)166
C4B—H4B···O31Cvii0.952.363.077 (2)132
C4B—H4B···N4Cvii0.952.603.509 (2)160
C6B—H6B···O21Cviii0.952.563.403 (2)148
C6C—H6C···O8Biv0.952.363.062 (2)130
C6D—H6D···O8Av0.952.373.119 (2)135
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x+1, y, z+1; (v) x+2, y, z; (vii) x, y+1, z+1; (viii) x, y+1, z; (ix) x+1, y, z; (xiii) x+1, y1, z.
 

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