Ammonium quercetin-5'-sulfonate form­amide solvate

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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-4H-1-benzopyran-2-yl)benzenesulfonate formamide solvate

Crystal data

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) Å^3

Data collection

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

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0846P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (9)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O3s^i	0.90	1.81	2.701 (3)	172
C8—H8···O1s^i	0.93	2.49	3.378 (4)	161
O4′—H4′···O7^ii	0.92	1.96	2.766 (3)	146
C6—H6···O3′^iii	0.93	2.48	3.350 (4)	157
O3—H3···O2s^iv	0.90	2.22	2.982 (3)	143
N1—H4n···O2s	0.92 (5)	1.94 (5)	2.845 (4)	168 (5)
N1—H2n···O3s^v	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···O4^vi	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···O1s^i	0.96 (5)	2.14 (5)	2.954 (5)	142 (5)
O3′—H3′···O1f^vii	0.89	1.79	2.668 (3)	170
C1f—H1f···O5^viii	0.96	2.34	3.303 (5)	179
N1—H1n···O1f^ix	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.