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The asymmetric unit of the title compound, C
9H
8NO
+·C
6H
3N
2O
4−·2H
2O, 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
CCDC reference: 627656
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (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
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−·2H2O | Z = 4 |
Mr = 349.30 | F(000) = 728 |
Triclinic, P1 | Dx = 1.530 Mg m−3 |
Hall symbol: -P 1 | Melting point = 442.6–445.1 K |
a = 6.8754 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0387 (15) Å | Cell parameters from 2861 reflections |
c = 19.338 (2) Å | θ = 2.8–27.4° |
α = 86.138 (2)° | µ = 0.12 mm−1 |
β = 80.977 (2)° | T = 130 K |
γ = 73.673 (2)° | Block, yellow |
V = 1516.6 (3) Å3 | 0.40 × 0.40 × 0.30 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5281 independent reflections |
Radiation source: sealed tube | 4475 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −7→8 |
Tmin = 0.93, Tmax = 0.97 | k = −13→14 |
8060 measured reflections | l = −15→22 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H 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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O8A | 0.95861 (19) | −0.22051 (10) | 0.09507 (7) | 0.0238 (4) | |
N1A | 0.8933 (2) | −0.12725 (13) | −0.03273 (7) | 0.0187 (4) | |
C2A | 0.8720 (3) | −0.08558 (15) | −0.09719 (9) | 0.0209 (5) | |
C3A | 0.7584 (3) | 0.02884 (15) | −0.10815 (9) | 0.0222 (5) | |
C4A | 0.6686 (3) | 0.09746 (15) | −0.05210 (9) | 0.0214 (5) | |
C5A | 0.5992 (3) | 0.11959 (15) | 0.07757 (9) | 0.0219 (5) | |
C6A | 0.6243 (3) | 0.06960 (15) | 0.14248 (9) | 0.0229 (6) | |
C7A | 0.7426 (3) | −0.04522 (15) | 0.15056 (9) | 0.0229 (6) | |
C8A | 0.8360 (3) | −0.11150 (14) | 0.09310 (9) | 0.0197 (5) | |
C9A | 0.8064 (2) | −0.06232 (14) | 0.02584 (9) | 0.0184 (5) | |
C10A | 0.6892 (2) | 0.05379 (14) | 0.01699 (9) | 0.0191 (5) | |
O8B | 0.5119 (2) | 0.26474 (11) | 0.43384 (7) | 0.0289 (4) | |
N1B | 0.3415 (2) | 0.34458 (13) | 0.56217 (7) | 0.0211 (5) | |
C2B | 0.2570 (3) | 0.37760 (16) | 0.62674 (9) | 0.0238 (6) | |
C3B | 0.1388 (3) | 0.49152 (16) | 0.63874 (10) | 0.0248 (6) | |
C4B | 0.1154 (3) | 0.56968 (15) | 0.58402 (10) | 0.0238 (6) | |
C5B | 0.1894 (3) | 0.61195 (15) | 0.45628 (10) | 0.0252 (6) | |
C6B | 0.2788 (3) | 0.57123 (15) | 0.39144 (10) | 0.0257 (6) | |
C7B | 0.3882 (3) | 0.45410 (15) | 0.38126 (10) | 0.0243 (6) | |
C8B | 0.4086 (3) | 0.37736 (15) | 0.43729 (9) | 0.0208 (5) | |
C9B | 0.3184 (2) | 0.41853 (14) | 0.50507 (9) | 0.0210 (5) | |
C10B | 0.2053 (3) | 0.53570 (14) | 0.51521 (9) | 0.0195 (5) | |
O21C | 0.15999 (19) | −0.16791 (10) | 0.30535 (6) | 0.0260 (4) | |
O22C | 0.48654 (18) | −0.16222 (10) | 0.28542 (6) | 0.0228 (4) | |
O31C | 0.0193 (2) | 0.23422 (10) | 0.30989 (7) | 0.0308 (4) | |
O32C | 0.1598 (3) | 0.07037 (11) | 0.25293 (7) | 0.0419 (5) | |
N1C | 0.3323 (2) | −0.10391 (12) | 0.43700 (7) | 0.0200 (4) | |
N4C | 0.1298 (2) | 0.13360 (12) | 0.43093 (7) | 0.0203 (4) | |
C2C | 0.2662 (2) | −0.05207 (14) | 0.37784 (9) | 0.0174 (5) | |
C3C | 0.1692 (2) | 0.06694 (14) | 0.37473 (9) | 0.0178 (5) | |
C5C | 0.1892 (3) | 0.08018 (15) | 0.48977 (9) | 0.0218 (5) | |
C6C | 0.2909 (3) | −0.03680 (15) | 0.49264 (9) | 0.0207 (5) | |
C21C | 0.3050 (3) | −0.13261 (14) | 0.31695 (9) | 0.0188 (5) | |
C31C | 0.1148 (3) | 0.12434 (14) | 0.30599 (9) | 0.0208 (5) | |
O21D | 0.63743 (19) | 0.32364 (10) | 0.19878 (6) | 0.0266 (4) | |
O22D | 0.96231 (19) | 0.33190 (10) | 0.18958 (6) | 0.0258 (4) | |
O31D | 0.5377 (2) | 0.72930 (10) | 0.16967 (6) | 0.0264 (4) | |
O32D | 0.6311 (2) | 0.56367 (11) | 0.23062 (7) | 0.0367 (5) | |
N1D | 0.8259 (2) | 0.37920 (12) | 0.04551 (7) | 0.0205 (5) | |
N4D | 0.6458 (2) | 0.61955 (12) | 0.04781 (7) | 0.0211 (5) | |
C2D | 0.7591 (2) | 0.43573 (14) | 0.10623 (9) | 0.0179 (5) | |
C3D | 0.6722 (2) | 0.55580 (14) | 0.10693 (9) | 0.0180 (5) | |
C5D | 0.7071 (3) | 0.56204 (15) | −0.01175 (9) | 0.0231 (5) | |
C6D | 0.7982 (3) | 0.44355 (15) | −0.01319 (9) | 0.0221 (5) | |
C21D | 0.7856 (3) | 0.35895 (14) | 0.17180 (9) | 0.0199 (5) | |
C31D | 0.6109 (3) | 0.61707 (14) | 0.17578 (9) | 0.0196 (5) | |
O1W | 0.5667 (2) | 0.17934 (13) | 0.31231 (7) | 0.0309 (5) | |
O2W | 1.0373 (2) | −0.30260 (13) | 0.21839 (7) | 0.0284 (4) | |
O3W | 0.2346 (2) | 0.47001 (12) | 0.18710 (7) | 0.0323 (5) | |
O4W | 0.7482 (2) | −0.05043 (12) | 0.33800 (7) | 0.0281 (4) | |
H1A | 0.970 (3) | −0.1983 (18) | −0.0256 (10) | 0.027 (5)* | |
H2A | 0.93400 | −0.13360 | −0.13610 | 0.0250* | |
H3A | 0.74390 | 0.05860 | −0.15440 | 0.0270* | |
H4A | 0.59170 | 0.17510 | −0.05950 | 0.0260* | |
H5A | 0.52170 | 0.19800 | 0.07320 | 0.0260* | |
H6A | 0.56040 | 0.11350 | 0.18290 | 0.0270* | |
H7A | 0.75820 | −0.07740 | 0.19620 | 0.0270* | |
H8A | 0.985 (3) | −0.2451 (19) | 0.1394 (12) | 0.041 (6)* | |
H1B | 0.429 (3) | 0.2701 (19) | 0.5531 (11) | 0.037 (6)* | |
H2B | 0.27690 | 0.32360 | 0.66490 | 0.0290* | |
H3B | 0.07510 | 0.51450 | 0.68470 | 0.0300* | |
H4B | 0.03790 | 0.64760 | 0.59230 | 0.0290* | |
H5B | 0.11670 | 0.69130 | 0.46180 | 0.0300* | |
H6B | 0.26710 | 0.62320 | 0.35210 | 0.0310* | |
H7B | 0.44800 | 0.42810 | 0.33550 | 0.0290* | |
H8B | 0.532 (4) | 0.235 (2) | 0.3910 (14) | 0.057 (7)* | |
H5C | 0.16100 | 0.12370 | 0.53110 | 0.0260* | |
H6C | 0.33250 | −0.07040 | 0.53570 | 0.0250* | |
H31C | −0.001 (4) | 0.268 (2) | 0.2680 (14) | 0.072 (8)* | |
H5D | 0.68780 | 0.60370 | −0.05480 | 0.0280* | |
H6D | 0.84220 | 0.40700 | −0.05710 | 0.0270* | |
H31D | 0.521 (4) | 0.759 (2) | 0.2090 (14) | 0.040 (8)* | |
H11W | 0.616 (4) | 0.218 (2) | 0.2751 (14) | 0.062 (8)* | |
H12W | 0.648 (4) | 0.105 (3) | 0.3151 (14) | 0.068 (9)* | |
H21W | 1.102 (4) | −0.268 (2) | 0.2426 (13) | 0.049 (7)* | |
H22W | 1.112 (4) | −0.374 (2) | 0.2136 (13) | 0.058 (8)* | |
H31W | 0.154 (4) | 0.427 (2) | 0.1901 (13) | 0.059 (8)* | |
H32W | 0.357 (4) | 0.425 (2) | 0.1939 (12) | 0.051 (7)* | |
H41W | 0.679 (4) | −0.089 (2) | 0.3201 (13) | 0.053 (8)* | |
H42W | 0.883 (4) | −0.090 (2) | 0.3266 (13) | 0.053 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O8A | 0.0294 (7) | 0.0192 (6) | 0.0183 (7) | 0.0011 (5) | −0.0052 (5) | 0.0011 (5) |
N1A | 0.0189 (7) | 0.0175 (8) | 0.0180 (8) | −0.0020 (6) | −0.0029 (6) | −0.0019 (6) |
C2A | 0.0220 (9) | 0.0225 (9) | 0.0182 (9) | −0.0059 (7) | −0.0033 (7) | −0.0014 (7) |
C3A | 0.0237 (9) | 0.0226 (9) | 0.0201 (9) | −0.0062 (7) | −0.0045 (7) | 0.0023 (7) |
C4A | 0.0195 (9) | 0.0186 (9) | 0.0266 (10) | −0.0051 (7) | −0.0059 (7) | 0.0017 (7) |
C5A | 0.0195 (9) | 0.0170 (9) | 0.0273 (10) | −0.0021 (7) | −0.0016 (7) | −0.0039 (7) |
C6A | 0.0221 (9) | 0.0255 (10) | 0.0202 (10) | −0.0054 (7) | 0.0009 (7) | −0.0082 (7) |
C7A | 0.0241 (10) | 0.0258 (10) | 0.0187 (9) | −0.0068 (8) | −0.0027 (7) | −0.0002 (7) |
C8A | 0.0187 (9) | 0.0193 (9) | 0.0205 (9) | −0.0047 (7) | −0.0025 (7) | −0.0004 (7) |
C9A | 0.0153 (8) | 0.0198 (9) | 0.0204 (9) | −0.0054 (7) | −0.0012 (7) | −0.0030 (7) |
C10A | 0.0166 (9) | 0.0189 (9) | 0.0226 (10) | −0.0064 (7) | −0.0024 (7) | −0.0011 (7) |
O8B | 0.0394 (8) | 0.0201 (7) | 0.0193 (7) | 0.0040 (6) | −0.0027 (6) | −0.0011 (5) |
N1B | 0.0222 (8) | 0.0184 (8) | 0.0208 (8) | −0.0022 (6) | −0.0039 (6) | −0.0008 (6) |
C2B | 0.0247 (9) | 0.0273 (10) | 0.0190 (10) | −0.0061 (8) | −0.0034 (7) | −0.0012 (7) |
C3B | 0.0212 (9) | 0.0292 (10) | 0.0225 (10) | −0.0038 (8) | −0.0019 (7) | −0.0067 (8) |
C4B | 0.0202 (9) | 0.0212 (9) | 0.0303 (11) | −0.0030 (7) | −0.0063 (8) | −0.0072 (8) |
C5B | 0.0254 (10) | 0.0179 (9) | 0.0332 (11) | −0.0048 (7) | −0.0095 (8) | 0.0013 (8) |
C6B | 0.0277 (10) | 0.0235 (10) | 0.0280 (11) | −0.0084 (8) | −0.0106 (8) | 0.0062 (8) |
C7B | 0.0250 (10) | 0.0279 (10) | 0.0211 (10) | −0.0080 (8) | −0.0054 (7) | −0.0001 (8) |
C8B | 0.0200 (9) | 0.0206 (9) | 0.0211 (9) | −0.0030 (7) | −0.0044 (7) | −0.0029 (7) |
C9B | 0.0185 (9) | 0.0193 (9) | 0.0268 (10) | −0.0055 (7) | −0.0067 (7) | −0.0024 (7) |
C10B | 0.0183 (9) | 0.0194 (9) | 0.0215 (9) | −0.0051 (7) | −0.0056 (7) | 0.0005 (7) |
O21C | 0.0254 (7) | 0.0242 (7) | 0.0290 (7) | −0.0057 (5) | −0.0053 (5) | −0.0071 (5) |
O22C | 0.0230 (7) | 0.0228 (7) | 0.0198 (6) | −0.0025 (5) | 0.0006 (5) | −0.0054 (5) |
O31C | 0.0480 (8) | 0.0173 (7) | 0.0203 (7) | 0.0059 (6) | −0.0114 (6) | −0.0015 (5) |
O32C | 0.0757 (11) | 0.0235 (7) | 0.0167 (7) | 0.0061 (7) | −0.0120 (7) | −0.0046 (6) |
N1C | 0.0214 (8) | 0.0186 (7) | 0.0181 (8) | −0.0033 (6) | −0.0014 (6) | −0.0008 (6) |
N4C | 0.0230 (8) | 0.0189 (7) | 0.0180 (8) | −0.0039 (6) | −0.0025 (6) | −0.0030 (6) |
C2C | 0.0158 (8) | 0.0186 (9) | 0.0175 (9) | −0.0049 (7) | −0.0015 (7) | 0.0007 (7) |
C3C | 0.0173 (8) | 0.0175 (8) | 0.0178 (9) | −0.0033 (7) | −0.0022 (7) | −0.0014 (7) |
C5C | 0.0258 (10) | 0.0222 (9) | 0.0168 (9) | −0.0049 (7) | −0.0033 (7) | −0.0030 (7) |
C6C | 0.0230 (9) | 0.0215 (9) | 0.0161 (9) | −0.0033 (7) | −0.0041 (7) | 0.0016 (7) |
C21C | 0.0247 (10) | 0.0133 (8) | 0.0164 (9) | −0.0013 (7) | −0.0058 (7) | 0.0026 (7) |
C31C | 0.0247 (9) | 0.0163 (9) | 0.0196 (9) | −0.0022 (7) | −0.0032 (7) | −0.0018 (7) |
O21D | 0.0312 (7) | 0.0241 (7) | 0.0240 (7) | −0.0085 (6) | −0.0027 (6) | 0.0032 (5) |
O22D | 0.0270 (7) | 0.0244 (7) | 0.0238 (7) | −0.0019 (5) | −0.0089 (5) | 0.0042 (5) |
O31D | 0.0392 (8) | 0.0177 (6) | 0.0178 (7) | −0.0002 (6) | −0.0036 (6) | −0.0022 (5) |
O32D | 0.0664 (10) | 0.0208 (7) | 0.0191 (7) | −0.0042 (7) | −0.0096 (7) | 0.0003 (6) |
N1D | 0.0216 (8) | 0.0192 (8) | 0.0193 (8) | −0.0027 (6) | −0.0037 (6) | −0.0012 (6) |
N4D | 0.0251 (8) | 0.0197 (8) | 0.0166 (8) | −0.0029 (6) | −0.0040 (6) | 0.0001 (6) |
C2D | 0.0168 (8) | 0.0186 (9) | 0.0179 (9) | −0.0037 (7) | −0.0030 (7) | −0.0020 (7) |
C3D | 0.0177 (9) | 0.0187 (9) | 0.0173 (9) | −0.0042 (7) | −0.0035 (7) | 0.0004 (7) |
C5D | 0.0275 (10) | 0.0227 (9) | 0.0161 (9) | −0.0021 (7) | −0.0040 (7) | 0.0012 (7) |
C6D | 0.0245 (9) | 0.0224 (9) | 0.0173 (9) | −0.0027 (7) | −0.0030 (7) | −0.0011 (7) |
C21D | 0.0267 (10) | 0.0125 (8) | 0.0185 (9) | −0.0012 (7) | −0.0036 (7) | −0.0047 (7) |
C31D | 0.0213 (9) | 0.0166 (9) | 0.0199 (10) | −0.0026 (7) | −0.0045 (7) | −0.0006 (7) |
O1W | 0.0438 (9) | 0.0249 (8) | 0.0206 (7) | −0.0069 (7) | 0.0011 (6) | −0.0007 (6) |
O2W | 0.0366 (8) | 0.0240 (7) | 0.0260 (8) | −0.0061 (6) | −0.0130 (6) | 0.0006 (6) |
O3W | 0.0315 (8) | 0.0270 (8) | 0.0381 (9) | −0.0061 (7) | −0.0073 (6) | −0.0010 (6) |
O4W | 0.0255 (8) | 0.0296 (7) | 0.0279 (8) | −0.0045 (6) | −0.0030 (6) | −0.0069 (6) |
Geometric parameters (Å, º) top
O8A—C8A | 1.348 (2) | C5A—C6A | 1.369 (2) |
O8A—H8A | 0.92 (2) | C5A—C10A | 1.416 (2) |
O8B—C8B | 1.343 (2) | C6A—C7A | 1.406 (3) |
O8B—H8B | 0.93 (3) | C7A—C8A | 1.375 (2) |
O21C—C21C | 1.243 (2) | C8A—C9A | 1.413 (2) |
O22C—C21C | 1.264 (2) | C9A—C10A | 1.418 (2) |
O31C—C31C | 1.302 (2) | C2A—H2A | 0.9500 |
O32C—C31C | 1.203 (2) | C3A—H3A | 0.9500 |
O31C—H31C | 0.90 (3) | C4A—H4A | 0.9500 |
O21D—C21D | 1.240 (2) | C5A—H5A | 0.9500 |
O22D—C21D | 1.263 (2) | C6A—H6A | 0.9500 |
O31D—C31D | 1.307 (2) | C7A—H7A | 0.9500 |
O32D—C31D | 1.209 (2) | C2B—C3B | 1.397 (3) |
O31D—H31D | 0.84 (3) | C3B—C4B | 1.366 (3) |
O1W—H12W | 0.92 (3) | C4B—C10B | 1.412 (3) |
O1W—H11W | 0.90 (3) | C5B—C10B | 1.412 (3) |
N1A—C9A | 1.377 (2) | C5B—C6B | 1.365 (3) |
N1A—C2A | 1.326 (2) | C6B—C7B | 1.410 (2) |
N1A—H1A | 0.88 (2) | C7B—C8B | 1.374 (3) |
O2W—H22W | 0.87 (2) | C8B—C9B | 1.417 (2) |
O2W—H21W | 0.89 (3) | C9B—C10B | 1.416 (2) |
N1B—C2B | 1.328 (2) | C2B—H2B | 0.9500 |
N1B—C9B | 1.371 (2) | C3B—H3B | 0.9500 |
N1B—H1B | 0.94 (2) | C4B—H4B | 0.9500 |
O3W—H31W | 0.85 (3) | C5B—H5B | 0.9500 |
O3W—H32W | 0.89 (3) | C6B—H6B | 0.9500 |
N1C—C2C | 1.346 (2) | C7B—H7B | 0.9500 |
N1C—C6C | 1.335 (2) | C2C—C21C | 1.519 (2) |
N4C—C5C | 1.332 (2) | C2C—C3C | 1.402 (2) |
N4C—C3C | 1.342 (2) | C3C—C31C | 1.507 (2) |
O4W—H41W | 0.87 (3) | C5C—C6C | 1.387 (2) |
O4W—H42W | 0.92 (3) | C5C—H5C | 0.9500 |
N1D—C6D | 1.338 (2) | C6C—H6C | 0.9500 |
N1D—C2D | 1.347 (2) | C2D—C21D | 1.522 (2) |
N4D—C5D | 1.332 (2) | C2D—C3D | 1.400 (2) |
N4D—C3D | 1.341 (2) | C3D—C31D | 1.509 (2) |
C2A—C3A | 1.400 (3) | C5D—C6D | 1.388 (2) |
C3A—C4A | 1.365 (2) | C5D—H5D | 0.9500 |
C4A—C10A | 1.416 (2) | C6D—H6D | 0.9500 |
| | | |
O1W···O21D | 2.7750 (19) | C2A···O32Cix | 3.043 (2) |
O1W···O4W | 2.743 (2) | C2B···C7Bx | 3.563 (3) |
O1W···O8B | 2.5597 (19) | C2B···O32Dx | 3.152 (2) |
O1W···C31C | 3.375 (3) | C2B···O22Civ | 3.239 (2) |
O1W···C3C | 3.403 (2) | C2B···C6Bx | 3.378 (3) |
O1W···C8B | 3.347 (2) | C2C···O4W | 3.288 (2) |
O2W···C8A | 3.404 (2) | C3A···C6Aix | 3.343 (3) |
O2W···O8A | 2.5967 (19) | C3A···C5Aix | 3.385 (3) |
O2W···O21Ci | 2.7839 (19) | C3A···C8Av | 3.272 (3) |
O3W···O21D | 2.868 (2) | C3A···C7Av | 3.458 (3) |
O3W···O22Dii | 2.825 (2) | C3A···O31Diii | 3.316 (2) |
O3W···C5Diii | 3.387 (2) | C3A···O32Cix | 3.027 (2) |
O4W···O22C | 2.8637 (19) | C3B···C6Bvii | 3.311 (3) |
O4W···C5Civ | 3.407 (2) | C3B···O31Cvii | 3.340 (2) |
O4W···O21Ci | 2.779 (2) | C3B···C7Bx | 3.453 (3) |
O4W···C2C | 3.288 (2) | C3B···O32Dx | 3.125 (2) |
O4W···O1W | 2.743 (2) | C3B···C7Bvii | 3.575 (3) |
O8A···C4Av | 3.280 (2) | C3C···O1W | 3.403 (2) |
O8A···O31Dvi | 3.221 (2) | C4A···O31Diii | 3.200 (2) |
O8A···C6Dv | 3.119 (2) | C4A···C10Aix | 3.414 (3) |
O8A···N1A | 2.6946 (19) | C4A···C8Av | 3.423 (3) |
O8A···O2W | 2.5967 (19) | C4A···O8Av | 3.280 (2) |
O8B···N1Civ | 3.1869 (19) | C4A···C9Aix | 3.366 (3) |
O8B···O1W | 2.5597 (19) | C4B···C6Bvii | 3.539 (3) |
O8B···C6Civ | 3.062 (2) | C4B···C7Bvii | 3.511 (3) |
O8B···N1B | 2.6891 (19) | C4B···C8Bx | 3.464 (3) |
O21C···C6Bvi | 3.403 (2) | C4B···C7Bx | 3.511 (3) |
O21C···O2Wii | 2.7839 (19) | C4B···C8Bvii | 3.563 (3) |
O21C···O32C | 2.9771 (18) | C4B···O31Cvii | 3.077 (2) |
O21C···N1C | 3.1941 (19) | C5A···C3Aix | 3.385 (3) |
O21C···O4Wii | 2.779 (2) | C5A···C2Aix | 3.339 (3) |
O21D···C6A | 3.344 (2) | C5B···C10Bvii | 3.597 (3) |
O21D···O1W | 2.7750 (19) | C5B···N1Bx | 3.371 (3) |
O21D···N1D | 3.1507 (18) | C5B···C9Bx | 3.493 (3) |
O21D···O32D | 2.9819 (18) | C5B···C9Bvii | 3.570 (3) |
O21D···O3W | 2.868 (2) | C5C···C6Cxii | 3.446 (3) |
O22C···C2Biv | 3.239 (2) | C5C···O4Wiv | 3.407 (2) |
O22C···C7A | 3.368 (2) | C5C···C6Civ | 3.532 (3) |
O22C···N1C | 3.0155 (18) | C5D···N1Dxi | 3.434 (3) |
O22C···C31Dvi | 3.347 (2) | C5D···C5Diii | 3.527 (3) |
O22C···O31Dvi | 2.5939 (17) | C5D···C6Diii | 3.451 (3) |
O22C···O4W | 2.8637 (19) | C5D···C6Dxi | 3.491 (3) |
O22C···O32C | 3.155 (2) | C5D···O3Wiii | 3.387 (2) |
O22D···N1D | 3.0449 (18) | C6A···O21D | 3.344 (2) |
O22D···C31Ci | 3.305 (2) | C6A···C2Av | 3.493 (3) |
O22D···O32D | 3.1241 (18) | C6A···C3Aix | 3.343 (3) |
O22D···O31Ci | 2.5705 (18) | C6B···C4Bvii | 3.539 (3) |
O22D···C2Av | 3.385 (2) | C6B···C3Bvii | 3.311 (3) |
O22D···O3Wi | 2.825 (2) | C6B···N1Bx | 3.315 (3) |
O31C···O22Dii | 2.5705 (18) | C6B···C2Bx | 3.378 (3) |
O31C···C3Bvii | 3.340 (2) | C6B···O21Cviii | 3.403 (2) |
O31C···C4Bvii | 3.077 (2) | C6C···C6Civ | 3.295 (3) |
O31C···N4C | 2.6799 (19) | C6C···C5Civ | 3.532 (3) |
O31C···C21Dii | 3.379 (2) | C6C···O8Biv | 3.062 (2) |
O31D···C8Aviii | 3.309 (2) | C6C···C5Cxii | 3.446 (3) |
O31D···N4D | 2.6776 (18) | C6D···C5Dxi | 3.491 (3) |
O31D···C3Aiii | 3.316 (2) | C6D···C5Diii | 3.451 (3) |
O31D···C7Aviii | 3.368 (2) | C6D···C6Dxi | 3.531 (3) |
O31D···C4Aiii | 3.200 (2) | C6D···O8Av | 3.119 (2) |
O31D···C21Cviii | 3.339 (2) | C7A···O22C | 3.368 (2) |
O31D···O22Cviii | 2.5939 (17) | C7A···C3Av | 3.458 (3) |
O31D···O8Aviii | 3.221 (2) | C7A···C2Av | 3.440 (3) |
O32C···O21C | 2.9771 (18) | C7A···O31Dvi | 3.368 (2) |
O32C···C3Aix | 3.027 (2) | C7B···C4Bvii | 3.511 (3) |
O32C···C21C | 2.666 (2) | C7B···C4Bx | 3.511 (3) |
O32C···O22C | 3.155 (2) | C7B···C3Bvii | 3.575 (3) |
O32C···C2Aix | 3.043 (2) | C7B···C2Bx | 3.563 (3) |
O32D···O22D | 3.1241 (18) | C7B···C3Bx | 3.453 (3) |
O32D···O21D | 2.9819 (18) | C8A···C4Av | 3.423 (3) |
O32D···C21D | 2.650 (2) | C8A···O31Dvi | 3.309 (2) |
O32D···C3Bx | 3.125 (2) | C8A···O2W | 3.404 (2) |
O32D···C2Bx | 3.152 (2) | C8A···C2Av | 3.524 (3) |
N1A···C10Av | 3.294 (2) | C8A···C3Av | 3.272 (3) |
N1A···O8A | 2.6946 (19) | C8B···O1W | 3.347 (2) |
N1A···N1Dv | 3.106 (2) | C8B···C10Bx | 3.383 (3) |
N1B···N1Civ | 3.127 (2) | C8B···C4Bx | 3.464 (3) |
N1B···C5Bx | 3.371 (3) | C8B···C4Bvii | 3.563 (3) |
N1B···O8B | 2.6891 (19) | C9A···C9Av | 3.398 (2) |
N1B···C6Bx | 3.315 (3) | C9A···C10Av | 3.466 (2) |
N1C···N1Biv | 3.127 (2) | C9A···C4Aix | 3.366 (3) |
N1C···O8Biv | 3.1869 (19) | C9B···C10Bvii | 3.567 (3) |
N1C···O22C | 3.0155 (18) | C9B···C5Bvii | 3.570 (3) |
N1C···N4C | 2.810 (2) | C9B···C9Bx | 3.560 (2) |
N1C···O21C | 3.1941 (19) | C9B···C5Bx | 3.493 (3) |
N1D···O22D | 3.0449 (18) | C9B···C10Bx | 3.430 (3) |
N1D···O21D | 3.1507 (18) | C10A···N1Av | 3.294 (2) |
N1D···N1Av | 3.106 (2) | C10A···C10Aix | 3.380 (2) |
N1D···N4D | 2.810 (2) | C10A···C4Aix | 3.414 (3) |
N1D···C5Dxi | 3.434 (3) | C10A···C9Av | 3.466 (2) |
N4C···N1C | 2.810 (2) | C10B···C10Bvii | 3.318 (3) |
N4C···O31C | 2.6799 (19) | C10B···C8Bx | 3.383 (3) |
N4D···N1D | 2.810 (2) | C10B···C9Bx | 3.430 (3) |
N4D···O31D | 2.6776 (18) | C10B···C5Bvii | 3.597 (3) |
N1C···H1Biv | 2.22 (2) | C10B···C9Bvii | 3.567 (3) |
N1D···H1Av | 2.26 (2) | C21C···O32C | 2.666 (2) |
N4C···H4Bvii | 2.6000 | C21C···O31Dvi | 3.339 (2) |
N4D···H4Aiii | 2.5500 | C21D···O31Ci | 3.379 (2) |
C2A···C5Aix | 3.339 (3) | C21D···O32D | 2.650 (2) |
C2A···C8Av | 3.524 (3) | C31C···O1W | 3.375 (3) |
C2A···C6Av | 3.493 (3) | C31C···O22Dii | 3.305 (2) |
C2A···O22Dv | 3.385 (2) | C31D···O22Cviii | 3.347 (2) |
C2A···C7Av | 3.440 (3) | | |
| | | |
C8A—O8A—H8A | 112.6 (14) | N1B—C9B—C8B | 119.90 (15) |
C8B—O8B—H8B | 114.4 (16) | C8B—C9B—C10B | 121.09 (15) |
C31C—O31C—H31C | 112.9 (15) | N1B—C9B—C10B | 119.01 (15) |
C31D—O31D—H31D | 109.4 (16) | C4B—C10B—C9B | 117.87 (15) |
H11W—O1W—H12W | 111 (2) | C4B—C10B—C5B | 123.72 (16) |
C2A—N1A—C9A | 122.66 (15) | C5B—C10B—C9B | 118.42 (16) |
C9A—N1A—H1A | 116.6 (12) | N1B—C2B—H2B | 120.00 |
C2A—N1A—H1A | 120.7 (12) | C3B—C2B—H2B | 120.00 |
H21W—O2W—H22W | 107 (2) | C2B—C3B—H3B | 120.00 |
C2B—N1B—C9B | 122.59 (15) | C4B—C3B—H3B | 120.00 |
C2B—N1B—H1B | 121.8 (13) | C10B—C4B—H4B | 120.00 |
C9B—N1B—H1B | 115.5 (13) | C3B—C4B—H4B | 120.00 |
H31W—O3W—H32W | 107 (2) | C6B—C5B—H5B | 120.00 |
C2C—N1C—C6C | 116.18 (14) | C10B—C5B—H5B | 120.00 |
C3C—N4C—C5C | 116.10 (14) | C5B—C6B—H6B | 119.00 |
H41W—O4W—H42W | 106 (2) | C7B—C6B—H6B | 119.00 |
C2D—N1D—C6D | 116.29 (14) | C8B—C7B—H7B | 120.00 |
C3D—N4D—C5D | 116.12 (14) | C6B—C7B—H7B | 120.00 |
N1A—C2A—C3A | 120.33 (16) | N1C—C2C—C21C | 114.64 (14) |
C2A—C3A—C4A | 119.70 (16) | C3C—C2C—C21C | 124.18 (15) |
C3A—C4A—C10A | 120.52 (16) | N1C—C2C—C3C | 121.18 (15) |
C6A—C5A—C10A | 119.66 (16) | N4C—C3C—C31C | 118.15 (14) |
C5A—C6A—C7A | 121.47 (16) | C2C—C3C—C31C | 119.83 (15) |
C6A—C7A—C8A | 120.77 (16) | N4C—C3C—C2C | 121.97 (15) |
C7A—C8A—C9A | 118.43 (15) | N4C—C5C—C6C | 122.19 (16) |
O8A—C8A—C7A | 125.39 (16) | N1C—C6C—C5C | 122.28 (16) |
O8A—C8A—C9A | 116.17 (15) | O21C—C21C—O22C | 126.34 (16) |
N1A—C9A—C10A | 118.75 (15) | O22C—C21C—C2C | 116.00 (16) |
C8A—C9A—C10A | 121.31 (15) | O21C—C21C—C2C | 117.53 (16) |
N1A—C9A—C8A | 119.94 (15) | O31C—C31C—C3C | 114.38 (15) |
C4A—C10A—C5A | 123.63 (15) | O32C—C31C—C3C | 120.99 (15) |
C5A—C10A—C9A | 118.33 (15) | O31C—C31C—O32C | 124.62 (17) |
C4A—C10A—C9A | 118.04 (15) | C6C—C5C—H5C | 119.00 |
C3A—C2A—H2A | 120.00 | N4C—C5C—H5C | 119.00 |
N1A—C2A—H2A | 120.00 | N1C—C6C—H6C | 119.00 |
C2A—C3A—H3A | 120.00 | C5C—C6C—H6C | 119.00 |
C4A—C3A—H3A | 120.00 | C3D—C2D—C21D | 124.09 (15) |
C3A—C4A—H4A | 120.00 | N1D—C2D—C21D | 114.73 (14) |
C10A—C4A—H4A | 120.00 | N1D—C2D—C3D | 121.18 (15) |
C6A—C5A—H5A | 120.00 | N4D—C3D—C2D | 122.03 (15) |
C10A—C5A—H5A | 120.00 | N4D—C3D—C31D | 118.29 (14) |
C5A—C6A—H6A | 119.00 | C2D—C3D—C31D | 119.66 (15) |
C7A—C6A—H6A | 119.00 | N4D—C5D—C6D | 122.37 (16) |
C6A—C7A—H7A | 120.00 | N1D—C6D—C5D | 121.96 (16) |
C8A—C7A—H7A | 120.00 | O22D—C21D—C2D | 115.54 (16) |
N1B—C2B—C3B | 120.20 (16) | O21D—C21D—C2D | 116.96 (17) |
C2B—C3B—C4B | 119.67 (17) | O21D—C21D—O22D | 127.30 (16) |
C3B—C4B—C10B | 120.60 (16) | O31D—C31D—O32D | 124.94 (16) |
C6B—C5B—C10B | 119.78 (16) | O31D—C31D—C3D | 114.10 (14) |
C5B—C6B—C7B | 121.73 (17) | O32D—C31D—C3D | 120.96 (15) |
C6B—C7B—C8B | 120.29 (17) | C6D—C5D—H5D | 119.00 |
O8B—C8B—C7B | 125.32 (16) | N4D—C5D—H5D | 119.00 |
O8B—C8B—C9B | 116.00 (15) | N1D—C6D—H6D | 119.00 |
C7B—C8B—C9B | 118.67 (16) | C5D—C6D—H6D | 119.00 |
| | | |
C9A—N1A—C2A—C3A | 0.3 (3) | C6B—C5B—C10B—C4B | −179.0 (2) |
C2A—N1A—C9A—C8A | −179.55 (18) | C6B—C5B—C10B—C9B | 1.3 (3) |
C2A—N1A—C9A—C10A | 0.1 (2) | C10B—C5B—C6B—C7B | −0.1 (3) |
C9B—N1B—C2B—C3B | 0.1 (3) | C5B—C6B—C7B—C8B | −0.4 (3) |
C2B—N1B—C9B—C8B | −178.57 (18) | C6B—C7B—C8B—C9B | −0.2 (3) |
C2B—N1B—C9B—C10B | 1.9 (3) | C6B—C7B—C8B—O8B | −178.9 (2) |
C6C—N1C—C2C—C3C | 3.2 (2) | C7B—C8B—C9B—N1B | −178.09 (17) |
C6C—N1C—C2C—C21C | −176.56 (16) | C7B—C8B—C9B—C10B | 1.4 (3) |
C2C—N1C—C6C—C5C | −1.2 (3) | O8B—C8B—C9B—C10B | −179.85 (17) |
C3C—N4C—C5C—C6C | 1.7 (3) | O8B—C8B—C9B—N1B | 0.7 (3) |
C5C—N4C—C3C—C31C | −176.92 (17) | N1B—C9B—C10B—C5B | 177.59 (17) |
C5C—N4C—C3C—C2C | 0.3 (2) | N1B—C9B—C10B—C4B | −2.1 (3) |
C2D—N1D—C6D—C5D | 0.4 (3) | C8B—C9B—C10B—C5B | −1.9 (3) |
C6D—N1D—C2D—C21D | 177.68 (16) | C8B—C9B—C10B—C4B | 178.37 (18) |
C6D—N1D—C2D—C3D | −2.1 (2) | N1C—C2C—C21C—O22C | −76.80 (19) |
C5D—N4D—C3D—C31D | 178.30 (17) | N1C—C2C—C21C—O21C | 99.36 (18) |
C5D—N4D—C3D—C2D | 0.0 (2) | N1C—C2C—C3C—N4C | −2.9 (2) |
C3D—N4D—C5D—C6D | −1.7 (3) | N1C—C2C—C3C—C31C | 174.29 (15) |
N1A—C2A—C3A—C4A | −0.3 (3) | C21C—C2C—C3C—N4C | 176.83 (16) |
C2A—C3A—C4A—C10A | −0.1 (3) | C21C—C2C—C3C—C31C | −6.0 (2) |
C3A—C4A—C10A—C5A | −179.52 (19) | C3C—C2C—C21C—O21C | −80.4 (2) |
C3A—C4A—C10A—C9A | 0.4 (3) | C3C—C2C—C21C—O22C | 103.44 (19) |
C10A—C5A—C6A—C7A | 1.8 (3) | N4C—C3C—C31C—O31C | −4.8 (2) |
C6A—C5A—C10A—C9A | −1.1 (3) | C2C—C3C—C31C—O32C | −2.6 (3) |
C6A—C5A—C10A—C4A | 178.88 (19) | N4C—C3C—C31C—O32C | 174.67 (19) |
C5A—C6A—C7A—C8A | −0.5 (3) | C2C—C3C—C31C—O31C | 177.85 (16) |
C6A—C7A—C8A—C9A | −1.4 (3) | N4C—C5C—C6C—N1C | −1.3 (3) |
C6A—C7A—C8A—O8A | 177.28 (19) | N1D—C2D—C3D—N4D | 2.0 (2) |
O8A—C8A—C9A—N1A | 2.9 (3) | N1D—C2D—C3D—C31D | −176.30 (15) |
C7A—C8A—C9A—C10A | 2.1 (3) | C21D—C2D—C3D—N4D | −177.78 (16) |
C7A—C8A—C9A—N1A | −178.32 (17) | C21D—C2D—C3D—C31D | 3.9 (2) |
O8A—C8A—C9A—C10A | −176.72 (15) | N1D—C2D—C21D—O21D | −94.22 (18) |
N1A—C9A—C10A—C5A | 179.54 (15) | N1D—C2D—C21D—O22D | 80.96 (18) |
N1A—C9A—C10A—C4A | −0.4 (2) | C3D—C2D—C21D—O21D | 85.6 (2) |
C8A—C9A—C10A—C4A | 179.18 (17) | C3D—C2D—C21D—O22D | −99.27 (19) |
C8A—C9A—C10A—C5A | −0.9 (2) | N4D—C3D—C31D—O31D | −0.4 (2) |
N1B—C2B—C3B—C4B | −1.9 (3) | N4D—C3D—C31D—O32D | 179.85 (17) |
C2B—C3B—C4B—C10B | 1.6 (3) | C2D—C3D—C31D—O31D | 177.93 (15) |
C3B—C4B—C10B—C5B | −179.3 (2) | C2D—C3D—C31D—O32D | −1.8 (3) |
C3B—C4B—C10B—C9B | 0.4 (3) | N4D—C5D—C6D—N1D | 1.5 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z; (vi) x, y−1, 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···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O8A | 0.88 (2) | 2.322 (19) | 2.6946 (19) | 105.3 (15) |
N1A—H1A···N1Dv | 0.88 (2) | 2.26 (2) | 3.106 (2) | 161.4 (17) |
N1B—H1B···O8B | 0.94 (2) | 2.29 (2) | 2.6891 (19) | 105.0 (15) |
N1B—H1B···N1Civ | 0.94 (2) | 2.22 (2) | 3.127 (2) | 161.8 (18) |
O8A—H8A···O2W | 0.92 (2) | 1.68 (2) | 2.5967 (19) | 175 (2) |
O8B—H8B···O1W | 0.90 (3) | 1.66 (3) | 2.5597 (19) | 179 (4) |
O31C—H31C···O22Dii | 0.90 (3) | 1.68 (3) | 2.5705 (18) | 180 (4) |
O31D—H31D···O22Cviii | 0.84 (3) | 1.76 (3) | 2.5939 (17) | 173 (2) |
O1W—H11W···O21D | 0.90 (3) | 1.90 (3) | 2.7750 (19) | 163 (3) |
O1W—H12W···O4W | 0.92 (3) | 1.85 (3) | 2.743 (2) | 164 (3) |
O2W—H21W···O21Ci | 0.89 (3) | 1.92 (2) | 2.7839 (19) | 163 (2) |
O2W—H22W···O3Wxiii | 0.87 (3) | 1.90 (2) | 2.753 (2) | 166 (3) |
O3W—H31W···O22Dii | 0.85 (3) | 1.98 (3) | 2.825 (2) | 176 (2) |
O3W—H32W···O21D | 0.89 (3) | 1.98 (3) | 2.868 (2) | 174 (2) |
O4W—H41W···O22C | 0.87 (3) | 2.00 (3) | 2.8637 (19) | 172 (2) |
O4W—H42W···O21Ci | 0.92 (3) | 1.87 (3) | 2.779 (2) | 178.2 (12) |
C2A—H2A···O22Dv | 0.95 | 2.53 | 3.385 (2) | 149 |
C2A—H2A···O32Cix | 0.95 | 2.46 | 3.043 (2) | 120 |
C2B—H2B···O22Civ | 0.95 | 2.41 | 3.239 (2) | 146 |
C3A—H3A···O32Cix | 0.95 | 2.43 | 3.027 (2) | 121 |
C4A—H4A···O31Diii | 0.95 | 2.52 | 3.200 (2) | 129 |
C4A—H4A···N4Diii | 0.95 | 2.55 | 3.482 (2) | 166 |
C4B—H4B···O31Cvii | 0.95 | 2.36 | 3.077 (2) | 132 |
C4B—H4B···N4Cvii | 0.95 | 2.60 | 3.509 (2) | 160 |
C6B—H6B···O21Cviii | 0.95 | 2.56 | 3.403 (2) | 148 |
C6C—H6C···O8Biv | 0.95 | 2.36 | 3.062 (2) | 130 |
C6D—H6D···O8Av | 0.95 | 2.37 | 3.119 (2) | 135 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, 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, y−1, z. |
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