The ammonium salt of 2,3-dihydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)benzenesulfonic acid (common name quercetin-5'-sulfonate), NH4+·C15H9O10S-·CH3NO, crystallizes as the formamide solvate. The presence of the sulfonate group on the flavonoid core increases the solubility of this compound in water. In the solid state, anion-anion, anion-cation and anion-solvent-cation assemblies are formed by numerous intermolecular hydrogen bonds.
Supporting information
CCDC reference: 239148
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.142
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C H3 N O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 Software (Kuma Diffraction, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).
ammonium
2,3-dihydroxy-5-(3,5,7-trihydroxy-4-oxo-4
H-1-benzopyran-2-yl)benzenesulfonate formamide solvate
top
Crystal data top
H4N+·C15H9O10S−·CH3NO | Z = 2 |
Mr = 444.37 | F(000) = 460 |
Triclinic, P1 | Dx = 1.713 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 7.878 (2) Å | Cell parameters from 40 reflections |
b = 10.584 (4) Å | θ = 6–19° |
c = 11.184 (4) Å | µ = 2.35 mm−1 |
α = 68.25 (3)° | T = 293 K |
β = 86.54 (2)° | Needle, orange |
γ = 84.40 (2)° | 0.41 × 0.11 × 0.09 mm |
V = 861.7 (5) Å3 | |
Data collection top
Kuma KM4 four-circle diffractometer | 1957 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 80.3°, θmin = 5.6° |
ω/2θ scans | h = −10→10 |
Absorption correction: for a cylinder mounted on the φ axis (KM-4; Kuma Diffraction, 1991) | k = −12→13 |
Tmin = 0.78, Tmax = 0.81 | l = 0→13 |
3838 measured reflections | 3 standard reflections every 100 reflections |
3666 independent reflections | intensity decay: 1.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0846P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3666 reflections | Δρmax = 0.42 e Å−3 |
290 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0048 (9) |
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 | Uiso*/Ueq | |
N1 | 0.2128 (5) | 1.0432 (4) | 0.5837 (3) | 0.0458 (7) | |
H1N | 0.249 (6) | 1.119 (5) | 0.591 (4) | 0.064* | |
H2N | 0.106 (6) | 1.038 (5) | 0.589 (5) | 0.064* | |
H3N | 0.235 (6) | 0.972 (5) | 0.646 (5) | 0.064* | |
H4N | 0.263 (6) | 1.036 (5) | 0.509 (5) | 0.064* | |
O1 | 0.5810 (3) | 0.5951 (2) | 0.1374 (2) | 0.0324 (5) | |
C2 | 0.5031 (4) | 0.5020 (3) | 0.2415 (3) | 0.0293 (6) | |
C3 | 0.5295 (4) | 0.3664 (3) | 0.2635 (3) | 0.0330 (7) | |
O3 | 0.4526 (3) | 0.2708 (2) | 0.3628 (2) | 0.0433 (6) | |
H3 | 0.4892 | 0.1882 | 0.3623 | 0.052* | |
C4 | 0.6411 (4) | 0.3179 (3) | 0.1805 (3) | 0.0321 (7) | |
O4 | 0.6666 (3) | 0.1916 (2) | 0.2042 (2) | 0.0424 (6) | |
C5 | 0.8187 (4) | 0.3837 (3) | −0.0230 (3) | 0.0317 (6) | |
O5 | 0.8524 (3) | 0.2522 (2) | −0.0092 (2) | 0.0447 (6) | |
H5 | 0.7864 | 0.2021 | 0.0616 | 0.054* | |
C6 | 0.8863 (4) | 0.4841 (3) | −0.1268 (3) | 0.0353 (7) | |
H6 | 0.9539 | 0.4612 | −0.1880 | 0.042* | |
C7 | 0.8535 (4) | 0.6201 (3) | −0.1403 (3) | 0.0316 (6) | |
O7 | 0.9293 (3) | 0.7127 (2) | −0.2430 (2) | 0.0402 (6) | |
H7 | 0.9065 | 0.8011 | −0.2531 | 0.048* | |
C8 | 0.7488 (4) | 0.6601 (3) | −0.0524 (3) | 0.0304 (6) | |
H8 | 0.7258 | 0.7514 | −0.0632 | 0.036* | |
C9 | 0.6814 (4) | 0.5567 (3) | 0.0515 (3) | 0.0284 (6) | |
C10 | 0.7140 (4) | 0.4187 (3) | 0.0703 (3) | 0.0296 (6) | |
C1' | 0.3984 (4) | 0.5708 (3) | 0.3171 (3) | 0.0274 (6) | |
C2' | 0.3135 (4) | 0.4970 (3) | 0.4331 (3) | 0.0319 (6) | |
H2' | 0.3197 | 0.4022 | 0.4628 | 0.038* | |
C3' | 0.2213 (4) | 0.5655 (3) | 0.5024 (3) | 0.0316 (6) | |
O3' | 0.1364 (3) | 0.5024 (2) | 0.6152 (2) | 0.0415 (6) | |
H3' | 0.1582 | 0.4126 | 0.6362 | 0.050* | |
C4' | 0.2112 (4) | 0.7079 (3) | 0.4599 (3) | 0.0300 (6) | |
O4' | 0.1232 (3) | 0.7743 (2) | 0.5310 (2) | 0.0400 (6) | |
H4' | 0.0654 | 0.7194 | 0.6030 | 0.048* | |
C5' | 0.2930 (4) | 0.7807 (3) | 0.3451 (3) | 0.0306 (6) | |
S1 | 0.29527 (11) | 0.95979 (7) | 0.29027 (8) | 0.0337 (2) | |
O1S | 0.3692 (3) | 1.0018 (2) | 0.1610 (2) | 0.0431 (6) | |
O2S | 0.3986 (3) | 0.9898 (2) | 0.3791 (2) | 0.0447 (6) | |
O3S | 0.1193 (3) | 1.0168 (2) | 0.2918 (3) | 0.0499 (7) | |
C6' | 0.3862 (4) | 0.7124 (3) | 0.2741 (3) | 0.0302 (6) | |
H6' | 0.4406 | 0.7621 | 0.1972 | 0.036* | |
O1F | 0.1998 (4) | 1.2317 (2) | −0.2929 (2) | 0.0500 (7) | |
C1F | 0.1793 (5) | 1.1738 (4) | −0.1751 (4) | 0.0505 (9) | |
H1F | 0.0833 | 1.1973 | −0.1277 | 0.061* | |
N1F | 0.2693 (5) | 1.0639 (4) | −0.1041 (3) | 0.0529 (8) | |
H2F | 0.237 (7) | 1.036 (5) | −0.030 (5) | 0.074* | |
H3F | 0.360 (6) | 1.025 (5) | −0.145 (5) | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0495 (19) | 0.0471 (17) | 0.0447 (18) | −0.0080 (14) | 0.0106 (15) | −0.0222 (14) |
O1 | 0.0404 (12) | 0.0263 (9) | 0.0295 (11) | −0.0041 (8) | 0.0126 (9) | −0.0107 (8) |
C2 | 0.0323 (15) | 0.0290 (14) | 0.0252 (14) | −0.0032 (11) | 0.0079 (11) | −0.0096 (11) |
C3 | 0.0387 (16) | 0.0273 (14) | 0.0320 (16) | −0.0047 (12) | 0.0109 (13) | −0.0108 (12) |
O3 | 0.0519 (14) | 0.0266 (10) | 0.0444 (14) | −0.0058 (9) | 0.0221 (11) | −0.0078 (10) |
C4 | 0.0336 (16) | 0.0280 (13) | 0.0342 (16) | −0.0046 (11) | 0.0086 (13) | −0.0116 (12) |
O4 | 0.0506 (14) | 0.0257 (10) | 0.0494 (14) | −0.0031 (9) | 0.0182 (11) | −0.0149 (10) |
C5 | 0.0315 (14) | 0.0280 (13) | 0.0368 (16) | 0.0008 (11) | 0.0055 (12) | −0.0150 (12) |
O5 | 0.0574 (15) | 0.0285 (10) | 0.0476 (14) | −0.0049 (10) | 0.0229 (12) | −0.0167 (10) |
C6 | 0.0356 (16) | 0.0370 (16) | 0.0340 (16) | 0.0018 (12) | 0.0067 (13) | −0.0162 (13) |
C7 | 0.0321 (15) | 0.0308 (14) | 0.0287 (15) | −0.0030 (11) | 0.0069 (12) | −0.0081 (12) |
O7 | 0.0502 (14) | 0.0298 (10) | 0.0339 (12) | −0.0024 (9) | 0.0194 (10) | −0.0070 (9) |
C8 | 0.0326 (15) | 0.0245 (12) | 0.0331 (15) | −0.0013 (10) | 0.0067 (12) | −0.0107 (11) |
C9 | 0.0326 (15) | 0.0286 (13) | 0.0244 (14) | −0.0029 (11) | 0.0037 (11) | −0.0108 (11) |
C10 | 0.0275 (14) | 0.0313 (14) | 0.0313 (15) | −0.0038 (11) | 0.0049 (12) | −0.0135 (12) |
C1' | 0.0262 (13) | 0.0270 (13) | 0.0298 (14) | −0.0014 (10) | 0.0052 (11) | −0.0123 (11) |
C2' | 0.0374 (15) | 0.0254 (13) | 0.0311 (15) | −0.0044 (11) | 0.0060 (12) | −0.0090 (12) |
C3' | 0.0373 (16) | 0.0301 (14) | 0.0260 (15) | −0.0060 (12) | 0.0092 (12) | −0.0094 (12) |
O3' | 0.0562 (15) | 0.0285 (10) | 0.0349 (12) | −0.0046 (10) | 0.0216 (11) | −0.0091 (9) |
C4' | 0.0338 (15) | 0.0280 (13) | 0.0279 (15) | −0.0002 (11) | 0.0070 (12) | −0.0118 (12) |
O4' | 0.0529 (14) | 0.0299 (11) | 0.0324 (12) | −0.0004 (9) | 0.0197 (10) | −0.0098 (9) |
C5' | 0.0345 (15) | 0.0266 (13) | 0.0291 (15) | −0.0015 (11) | 0.0069 (12) | −0.0097 (11) |
S1 | 0.0411 (4) | 0.0236 (3) | 0.0331 (4) | −0.0014 (3) | 0.0125 (3) | −0.0091 (3) |
O1S | 0.0613 (16) | 0.0287 (10) | 0.0329 (12) | −0.0050 (10) | 0.0150 (11) | −0.0060 (9) |
O2S | 0.0559 (15) | 0.0372 (12) | 0.0448 (14) | −0.0119 (10) | 0.0073 (11) | −0.0189 (10) |
O3S | 0.0431 (14) | 0.0284 (11) | 0.0688 (18) | 0.0029 (9) | 0.0150 (12) | −0.0108 (11) |
C6' | 0.0334 (15) | 0.0288 (14) | 0.0286 (15) | −0.0002 (11) | 0.0058 (12) | −0.0125 (11) |
O1F | 0.0739 (18) | 0.0351 (12) | 0.0372 (13) | −0.0014 (12) | 0.0041 (12) | −0.0102 (10) |
C1F | 0.059 (2) | 0.046 (2) | 0.047 (2) | 0.0003 (17) | 0.0119 (18) | −0.0205 (17) |
N1F | 0.064 (2) | 0.0469 (17) | 0.0407 (17) | 0.0027 (15) | 0.0064 (16) | −0.0107 (14) |
Geometric parameters (Å, º) top
N1—H1n | 0.91 (5) | C8—H8 | 0.9300 |
N1—H2n | 0.84 (5) | C9—C10 | 1.397 (4) |
N1—H3n | 0.83 (5) | C1'—C6' | 1.389 (4) |
N1—H4n | 0.92 (5) | C1'—C2' | 1.410 (4) |
O1—C9 | 1.359 (3) | C2'—C3' | 1.379 (4) |
O1—C2 | 1.373 (3) | C2'—H2' | 0.9300 |
C2—C3 | 1.361 (4) | C3'—O3' | 1.358 (3) |
C2—C1' | 1.475 (4) | C3'—C4' | 1.398 (4) |
C3—O3 | 1.352 (3) | O3'—H3' | 0.8919 |
C3—C4 | 1.437 (4) | C4'—O4' | 1.364 (3) |
O3—H3 | 0.8950 | C4'—C5' | 1.387 (4) |
C4—O4 | 1.260 (3) | O4'—H4' | 0.9240 |
C4—C10 | 1.430 (4) | C5'—C6' | 1.394 (4) |
C5—O5 | 1.344 (3) | C5'—S1 | 1.764 (3) |
C5—C6 | 1.371 (4) | S1—O1s | 1.449 (2) |
C5—C10 | 1.424 (4) | S1—O2s | 1.460 (3) |
O5—H5 | 0.9335 | S1—O3s | 1.459 (3) |
C6—C7 | 1.390 (4) | C6'—H6' | 0.9300 |
C6—H6 | 0.9300 | O1f—C1f | 1.238 (4) |
C7—O7 | 1.354 (3) | C1f—N1f | 1.307 (5) |
C7—C8 | 1.403 (4) | C1f—H1f | 0.9626 |
O7—H7 | 0.9014 | N1f—H2f | 0.80 (5) |
C8—C9 | 1.388 (4) | N1f—H3f | 0.96 (5) |
| | | |
H1n—N1—H2n | 116 (5) | C9—C10—C4 | 119.6 (3) |
H1n—N1—H3n | 114 (5) | C5—C10—C4 | 122.3 (3) |
H2n—N1—H3n | 96 (4) | C6'—C1'—C2' | 119.0 (3) |
H1n—N1—H4n | 107 (4) | C6'—C1'—C2 | 119.0 (3) |
H2n—N1—H4n | 114 (4) | C2'—C1'—C2 | 122.0 (2) |
H3n—N1—H4n | 110 (4) | C3'—C2'—C1' | 119.9 (3) |
C9—O1—C2 | 122.0 (2) | C3'—C2'—H2' | 120.0 |
C3—C2—O1 | 120.0 (2) | C1'—C2'—H2' | 120.0 |
C3—C2—C1' | 129.0 (3) | O3'—C3'—C2' | 123.7 (3) |
O1—C2—C1' | 111.0 (2) | O3'—C3'—C4' | 115.3 (3) |
O3—C3—C2 | 122.4 (3) | C2'—C3'—C4' | 121.0 (3) |
O3—C3—C4 | 116.6 (3) | C3'—O3'—H3' | 107.7 |
C2—C3—C4 | 121.0 (3) | O4'—C4'—C5' | 120.4 (2) |
C3—O3—H3 | 108.8 | O4'—C4'—C3' | 120.4 (2) |
O4—C4—C10 | 123.0 (3) | C5'—C4'—C3' | 119.1 (3) |
O4—C4—C3 | 119.9 (3) | C4'—O4'—H4' | 115.3 |
C10—C4—C3 | 117.1 (3) | C4'—C5'—C6' | 120.3 (3) |
O5—C5—C6 | 119.8 (3) | C4'—C5'—S1 | 121.5 (2) |
O5—C5—C10 | 120.1 (3) | C6'—C5'—S1 | 118.1 (2) |
C6—C5—C10 | 120.2 (3) | O1s—S1—O3s | 111.92 (16) |
C5—O5—H5 | 106.1 | O1s—S1—O2s | 112.48 (15) |
C5—C6—C7 | 119.9 (3) | O3s—S1—O2s | 111.29 (16) |
C5—C6—H6 | 120.1 | O1s—S1—C5' | 106.08 (14) |
C7—C6—H6 | 120.1 | O3s—S1—C5' | 107.62 (15) |
O7—C7—C6 | 116.3 (3) | O2s—S1—C5' | 107.07 (15) |
O7—C7—C8 | 121.5 (3) | C1'—C6'—C5' | 120.7 (3) |
C6—C7—C8 | 122.2 (3) | C1'—C6'—H6' | 119.7 |
C7—O7—H7 | 116.6 | C5'—C6'—H6' | 119.7 |
C9—C8—C7 | 116.8 (3) | O1f—C1f—N1f | 124.7 (4) |
C9—C8—H8 | 121.6 | O1f—C1f—H1f | 122.8 |
C7—C8—H8 | 121.6 | N1f—C1f—H1f | 112.0 |
O1—C9—C8 | 116.9 (2) | C1f—N1f—H2f | 113 (4) |
O1—C9—C10 | 120.2 (2) | C1f—N1f—H3f | 119 (3) |
C8—C9—C10 | 122.8 (3) | H2f—N1f—H3f | 128 (5) |
C9—C10—C5 | 118.1 (3) | | |
| | | |
C9—O1—C2—C3 | 2.0 (4) | C3—C4—C10—C9 | 3.0 (5) |
C9—O1—C2—C1' | −178.5 (3) | O4—C4—C10—C5 | 1.3 (5) |
O1—C2—C3—O3 | −178.3 (3) | C3—C4—C10—C5 | −176.4 (3) |
C1'—C2—C3—O3 | 2.4 (6) | C3—C2—C1'—C6' | −178.2 (3) |
O1—C2—C3—C4 | 1.2 (5) | O1—C2—C1'—C6' | 2.4 (4) |
C1'—C2—C3—C4 | −178.1 (3) | C3—C2—C1'—C2' | 3.2 (5) |
O3—C3—C4—O4 | −1.9 (5) | O1—C2—C1'—C2' | −176.1 (3) |
C2—C3—C4—O4 | 178.5 (3) | C6'—C1'—C2'—C3' | −0.5 (5) |
O3—C3—C4—C10 | 175.9 (3) | C2—C1'—C2'—C3' | 178.0 (3) |
C2—C3—C4—C10 | −3.7 (5) | C1'—C2'—C3'—O3' | −179.7 (3) |
O5—C5—C6—C7 | −179.2 (3) | C1'—C2'—C3'—C4' | −0.5 (5) |
C10—C5—C6—C7 | 0.5 (5) | O3'—C3'—C4'—O4' | 1.0 (5) |
C5—C6—C7—O7 | 177.9 (3) | C2'—C3'—C4'—O4' | −178.3 (3) |
C5—C6—C7—C8 | −1.6 (5) | O3'—C3'—C4'—C5' | −179.5 (3) |
O7—C7—C8—C9 | −178.2 (3) | C2'—C3'—C4'—C5' | 1.2 (5) |
C6—C7—C8—C9 | 1.3 (5) | O4'—C4'—C5'—C6' | 178.5 (3) |
C2—O1—C9—C8 | 177.9 (3) | C3'—C4'—C5'—C6' | −1.0 (5) |
C2—O1—C9—C10 | −2.7 (4) | O4'—C4'—C5'—S1 | 3.0 (4) |
C7—C8—C9—O1 | 179.5 (3) | C3'—C4'—C5'—S1 | −176.5 (2) |
C7—C8—C9—C10 | 0.1 (5) | C4'—C5'—S1—O1s | −172.0 (3) |
O1—C9—C10—C5 | 179.5 (3) | C6'—C5'—S1—O1s | 12.4 (3) |
C8—C9—C10—C5 | −1.1 (5) | C4'—C5'—S1—O3s | −52.1 (3) |
O1—C9—C10—C4 | 0.0 (4) | C6'—C5'—S1—O3s | 132.3 (3) |
C8—C9—C10—C4 | 179.4 (3) | C4'—C5'—S1—O2s | 67.7 (3) |
O5—C5—C10—C9 | −179.5 (3) | C6'—C5'—S1—O2s | −107.9 (3) |
C6—C5—C10—C9 | 0.8 (5) | C2'—C1'—C6'—C5' | 0.7 (5) |
O5—C5—C10—C4 | 0.0 (5) | C2—C1'—C6'—C5' | −177.9 (3) |
C6—C5—C10—C4 | −179.7 (3) | C4'—C5'—C6'—C1' | 0.1 (5) |
O4—C4—C10—C9 | −179.2 (3) | S1—C5'—C6'—C1' | 175.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.93 | 1.78 | 2.623 (3) | 149 |
O3—H3···O4 | 0.90 | 2.18 | 2.675 (3) | 114 |
C2′—H2′···O3 | 0.93 | 2.24 | 2.886 (4) | 126 |
C6′—H6′···O1 | 0.93 | 2.28 | 2.643 (3) | 103 |
O7—H7···O3si | 0.90 | 1.81 | 2.701 (3) | 172 |
C8—H8···O1si | 0.93 | 2.49 | 3.378 (4) | 161 |
O4′—H4′···O7ii | 0.92 | 1.96 | 2.766 (3) | 146 |
C6—H6···O3′iii | 0.93 | 2.48 | 3.350 (4) | 157 |
O3—H3···O2siv | 0.90 | 2.22 | 2.982 (3) | 143 |
N1—H4n···O2s | 0.92 (5) | 1.94 (5) | 2.845 (4) | 168 (5) |
N1—H2n···O3sv | 0.84 (5) | 2.15 (5) | 2.901 (4) | 149 (5) |
N1—H2n···O4′v | 0.84 (5) | 2.58 (5) | 3.155 (5) | 127 (5) |
N1—H3n···O4vi | 0.83 (5) | 2.04 (5) | 2.855 (5) | 170 (5) |
N1f—H2f···O1s | 0.80 (5) | 2.32 (5) | 2.929 (4) | 133 (5) |
N1f—H3f···O1si | 0.96 (5) | 2.14 (5) | 2.954 (5) | 142 (5) |
O3′—H3′···O1fvii | 0.89 | 1.79 | 2.668 (3) | 170 |
C1f—H1f···O5viii | 0.96 | 2.34 | 3.303 (5) | 179 |
N1—H1n···O1fix | 0.91 (5) | 2.06 (5) | 2.808 (4) | 138 (5) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z+1; (iii) x+1, y, z−1; (iv) x, y−1, z; (v) −x, −y+2, −z+1; (vi) −x+1, −y+1, −z+1; (vii) x, y−1, z+1; (viii) x−1, y+1, z; (ix) x, y, z+1. |