Bis(8-hy­droxy­quinolinium) naphthalene-1,5-di­sulfonate tetra­hydrate

Nazarov, Y.E.; Turaev, K.K.; Alimnazarov, B.K.; Suyunov, J.R.; Umirova, G.A.; Ibragimov, B.T.; Ashurov, J.M.

doi:10.1107/S2414314624005704

Bis(8-hydroxyquinolinium) naphthalene-1,5-disulfonate tetrahydrate

Y. E. Nazarov, K. K. Turaev, B. K. Alimnazarov, J. R. Suyunov, G. A. Umirova, B. T. Ibragimov and J. M. Ashurov

The interaction between 8-hydroxyquinoline (8HQ, C₉H₇NO) and naphthalene-1,5-disulfonic acid (H₂NDS, C₁₀H₈O₆S₂) in aqueous media results in the formation of the salt hydrate bis(8-hydroxyquinolinium) naphthalene-1,5-disulfonate tetrahydrate, 2C₉H₈NO⁺·C₁₀H₆O₆S₂²⁻·4H₂O. The asymmetric unit comprises one protonated 8HQ⁺ cation, half of an NDS^2– dianion symmetrically disposed around a center of inversion, and two water molecules. Within the crystal structure, these components are organized into chains along the [010] and [10 $\overline{1}$ ] directions through O—H

O and N—H

O hydrogen-bonding interactions, forming a di-periodic network parallel to (101). Additional stabilizing interactions such as C—H

O, C—H

π, and π–π interactions extend this arrangement into a tri-periodic network structure

Keywords: naphthalene-1,5-disulfonate; 8-hydroxyquinoline; crystal structure; hydrogen bonds; organic salt.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314624005704/wm4216sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314624005704/wm4216Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314624005704/wm4216Isup3.cml Supplementary material

CCDC reference: 2256736

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.002 Å
R factor = 0.031
wR factor = 0.089
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
              H1WA  H1WB  H2WA  H2WB
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
              H1WA    H1WB    H2WA    H2WB
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........      3.800 Note
              Predicted wR2: Based on SigI   2  2.33 or SHELX Weight  8.41       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Bis(8-hydroxyquinolinium) naphthalene-1,5-disulfonate tetrahydrate top

Crystal data top

2C₉H₈NO⁺·C₁₀H₆O₆S₂²⁻·4H₂O	F(000) = 680
M_r = 650.66	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 7.55855 (8) Å	Cell parameters from 9285 reflections
b = 12.16674 (13) Å	θ = 2.8–71.2°
c = 16.00467 (17) Å	µ = 2.25 mm⁻¹
β = 94.7152 (10)°	T = 290 K
V = 1466.86 (3) Å³	Block, light yellow
Z = 2	0.32 × 0.3 × 0.28 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2841 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2621 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.4°, θ_min = 4.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −14→14
T_min = 0.820, T_max = 1.000	l = −19→19
14094 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0501P)² + 0.303P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2841 reflections	Δρ_max = 0.20 e Å⁻³
214 parameters	Δρ_min = −0.29 e Å⁻³
2 restraints	Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: intrinsic phasing	Extinction coefficient: 0.0023 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms attached to the N and O atoms were located from a difference-Fourier map and refined with bond-length restraints of 0.86 (1) Å and 0.82 (1) Å, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.12659 (4)	0.52366 (3)	0.29817 (2)	0.03571 (13)
O2	0.16257 (16)	0.40840 (9)	0.28388 (7)	0.0539 (3)
O3	0.28637 (14)	0.58461 (9)	0.32385 (6)	0.0451 (3)
O4	0.02239 (15)	0.57423 (10)	0.22875 (6)	0.0525 (3)
C10	−0.00953 (17)	0.52607 (10)	0.38419 (8)	0.0315 (3)
C11	0.05915 (16)	0.49755 (10)	0.46738 (8)	0.0297 (3)
C12	0.23846 (17)	0.46556 (11)	0.48773 (9)	0.0351 (3)
H12	0.315658	0.460895	0.445520	0.042*
C13	0.29860 (18)	0.44165 (13)	0.56821 (9)	0.0407 (3)
H13	0.417007	0.422577	0.580589	0.049*
C14	−0.18313 (18)	0.55446 (12)	0.36709 (9)	0.0379 (3)
H14	−0.225612	0.571361	0.312413	0.045*
O1	0.60496 (18)	0.47210 (9)	0.18830 (7)	0.0538 (3)
N1	0.68475 (17)	0.64774 (10)	0.09816 (8)	0.0415 (3)
C1	0.6624 (2)	0.45179 (12)	0.11258 (9)	0.0409 (3)
C2	0.6827 (2)	0.35003 (13)	0.07829 (10)	0.0500 (4)
H2	0.659051	0.287453	0.108831	0.060*
C3	0.7392 (2)	0.33952 (15)	−0.00293 (11)	0.0563 (4)
H3	0.750754	0.269640	−0.025395	0.068*
C4	0.7774 (2)	0.42843 (15)	−0.04946 (10)	0.0538 (4)
H4	0.814252	0.419332	−0.103052	0.065*
C5	0.7981 (2)	0.63185 (15)	−0.05880 (10)	0.0520 (4)
H5	0.836512	0.627362	−0.112434	0.062*
C6	0.7791 (2)	0.73209 (15)	−0.02321 (11)	0.0550 (4)
H6	0.804189	0.795738	−0.052154	0.066*
C7	0.7214 (2)	0.73849 (13)	0.05723 (11)	0.0500 (4)
H7	0.708614	0.806722	0.082224	0.060*
C8	0.70289 (18)	0.54549 (12)	0.06544 (9)	0.0370 (3)
C9	0.7607 (2)	0.53461 (13)	−0.01585 (9)	0.0426 (3)
O1W	0.49949 (17)	0.31023 (10)	0.28209 (9)	0.0626 (3)
H1WA	0.392446	0.331508	0.282471	0.094*
H1WB	0.491769	0.242369	0.269682	0.094*
O2W	0.53570 (16)	0.71260 (10)	0.24017 (8)	0.0556 (3)
H2WA	0.480634	0.773241	0.233271	0.083*
H2WB	0.460317	0.669091	0.258790	0.083*
H1A	0.643 (3)	0.6562 (18)	0.1467 (8)	0.069 (6)*
H1	0.581 (3)	0.4147 (13)	0.2114 (14)	0.086 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0424 (2)	0.0381 (2)	0.02794 (19)	−0.00473 (12)	0.01084 (14)	−0.00284 (12)
O2	0.0634 (7)	0.0416 (6)	0.0599 (7)	−0.0036 (5)	0.0242 (6)	−0.0135 (5)
O3	0.0471 (6)	0.0540 (6)	0.0360 (5)	−0.0140 (5)	0.0142 (4)	−0.0021 (4)
O4	0.0584 (7)	0.0706 (8)	0.0291 (5)	−0.0020 (5)	0.0078 (5)	0.0066 (5)
C10	0.0356 (7)	0.0308 (6)	0.0289 (6)	−0.0024 (5)	0.0074 (5)	0.0001 (5)
C11	0.0312 (6)	0.0285 (6)	0.0300 (6)	−0.0018 (5)	0.0066 (5)	0.0002 (5)
C12	0.0317 (7)	0.0393 (7)	0.0356 (7)	0.0018 (5)	0.0102 (5)	0.0026 (5)
C13	0.0307 (7)	0.0489 (8)	0.0428 (8)	0.0052 (6)	0.0047 (6)	0.0054 (6)
C14	0.0385 (7)	0.0442 (8)	0.0309 (7)	0.0004 (6)	0.0021 (5)	0.0043 (5)
O1	0.0785 (8)	0.0460 (7)	0.0388 (6)	−0.0095 (6)	0.0159 (6)	0.0057 (5)
N1	0.0483 (7)	0.0403 (6)	0.0360 (6)	−0.0024 (5)	0.0041 (5)	0.0042 (5)
C1	0.0443 (8)	0.0437 (8)	0.0345 (7)	−0.0027 (6)	0.0017 (6)	0.0049 (6)
C2	0.0571 (9)	0.0407 (8)	0.0518 (9)	−0.0019 (7)	0.0026 (7)	0.0059 (7)
C3	0.0661 (10)	0.0474 (9)	0.0555 (10)	0.0066 (8)	0.0056 (8)	−0.0076 (7)
C4	0.0599 (10)	0.0613 (10)	0.0409 (8)	0.0071 (8)	0.0092 (7)	−0.0043 (7)
C5	0.0525 (9)	0.0649 (11)	0.0398 (8)	0.0007 (7)	0.0104 (7)	0.0136 (7)
C6	0.0582 (10)	0.0532 (10)	0.0543 (10)	−0.0050 (8)	0.0090 (8)	0.0210 (8)
C7	0.0570 (9)	0.0396 (8)	0.0532 (9)	−0.0028 (7)	0.0033 (7)	0.0076 (7)
C8	0.0370 (7)	0.0413 (7)	0.0321 (7)	−0.0018 (5)	0.0000 (5)	0.0029 (5)
C9	0.0400 (7)	0.0533 (9)	0.0344 (7)	0.0013 (6)	0.0033 (6)	0.0046 (6)
O1W	0.0647 (8)	0.0529 (7)	0.0722 (8)	0.0003 (6)	0.0171 (7)	0.0131 (6)
O2W	0.0629 (7)	0.0451 (6)	0.0618 (7)	0.0057 (5)	0.0236 (6)	0.0069 (5)

Geometric parameters (Å, º) top

S1—O2	1.4503 (11)	C1—C8	1.414 (2)
S1—O3	1.4476 (10)	C2—H2	0.9300
S1—O4	1.4455 (11)	C2—C3	1.407 (2)
S1—C10	1.7853 (13)	C3—H3	0.9300
C10—C11	1.4314 (18)	C3—C4	1.358 (3)
C10—C14	1.3627 (19)	C4—H4	0.9300
C11—C11ⁱ	1.431 (2)	C4—C9	1.409 (2)
C11—C12	1.4219 (18)	C5—H5	0.9300
C12—H12	0.9300	C5—C6	1.359 (3)
C12—C13	1.362 (2)	C5—C9	1.409 (2)
C13—H13	0.9300	C6—H6	0.9300
C13—C14ⁱ	1.409 (2)	C6—C7	1.395 (2)
C14—H14	0.9300	C7—H7	0.9300
O1—C1	1.3433 (19)	C8—C9	1.412 (2)
O1—H1	0.819 (10)	O1W—H1WA	0.8500
N1—C7	1.3246 (19)	O1W—H1WB	0.8501
N1—C8	1.3611 (19)	O2W—H2WA	0.8498
N1—H1A	0.868 (9)	O2W—H2WB	0.8495
C1—C2	1.368 (2)

O2—S1—C10	105.37 (6)	C2—C1—C8	118.63 (14)
O3—S1—O2	112.16 (7)	C1—C2—H2	119.8
O3—S1—C10	107.03 (6)	C1—C2—C3	120.36 (15)
O4—S1—O2	112.81 (7)	C3—C2—H2	119.8
O4—S1—O3	112.91 (7)	C2—C3—H3	119.0
O4—S1—C10	105.88 (6)	C4—C3—C2	121.91 (16)
C11—C10—S1	121.69 (10)	C4—C3—H3	119.0
C14—C10—S1	117.11 (10)	C3—C4—H4	120.3
C14—C10—C11	121.19 (12)	C3—C4—C9	119.43 (15)
C11ⁱ—C11—C10	117.91 (14)	C9—C4—H4	120.3
C12—C11—C10	123.05 (12)	C6—C5—H5	119.4
C12—C11—C11ⁱ	119.03 (14)	C6—C5—C9	121.12 (15)
C11—C12—H12	119.6	C9—C5—H5	119.4
C13—C12—C11	120.86 (12)	C5—C6—H6	120.4
C13—C12—H12	119.6	C5—C6—C7	119.28 (15)
C12—C13—H13	119.7	C7—C6—H6	120.4
C12—C13—C14ⁱ	120.62 (13)	N1—C7—C6	120.25 (15)
C14ⁱ—C13—H13	119.7	N1—C7—H7	119.9
C10—C14—C13ⁱ	120.36 (13)	C6—C7—H7	119.9
C10—C14—H14	119.8	N1—C8—C1	119.89 (13)
C13ⁱ—C14—H14	119.8	N1—C8—C9	119.25 (13)
C1—O1—H1	110.6 (17)	C9—C8—C1	120.85 (14)
C7—N1—C8	122.67 (13)	C4—C9—C8	118.80 (14)
C7—N1—H1A	116.7 (15)	C5—C9—C4	123.77 (15)
C8—N1—H1A	120.6 (15)	C5—C9—C8	117.43 (14)
O1—C1—C2	125.70 (14)	H1WA—O1W—H1WB	104.5
O1—C1—C8	115.67 (13)	H2WA—O2W—H2WB	104.5

S1—C10—C11—C11ⁱ	179.61 (12)	N1—C8—C9—C4	−179.40 (14)
S1—C10—C11—C12	0.00 (18)	N1—C8—C9—C5	0.5 (2)
S1—C10—C14—C13ⁱ	−179.89 (11)	C1—C2—C3—C4	0.8 (3)
O2—S1—C10—C11	69.66 (12)	C1—C8—C9—C4	0.0 (2)
O2—S1—C10—C14	−109.23 (12)	C1—C8—C9—C5	179.91 (14)
O3—S1—C10—C11	−49.90 (12)	C2—C1—C8—N1	−179.68 (14)
O3—S1—C10—C14	131.21 (11)	C2—C1—C8—C9	0.9 (2)
O4—S1—C10—C11	−170.60 (10)	C2—C3—C4—C9	0.1 (3)
O4—S1—C10—C14	10.52 (13)	C3—C4—C9—C5	179.58 (16)
C10—C11—C12—C13	178.45 (13)	C3—C4—C9—C8	−0.5 (2)
C11—C10—C14—C13ⁱ	1.2 (2)	C5—C6—C7—N1	−0.4 (3)
C11ⁱ—C11—C12—C13	−1.1 (2)	C6—C5—C9—C4	179.83 (16)
C11—C12—C13—C14ⁱ	1.5 (2)	C6—C5—C9—C8	0.0 (2)
C14—C10—C11—C11ⁱ	−1.6 (2)	C7—N1—C8—C1	179.67 (14)
C14—C10—C11—C12	178.84 (13)	C7—N1—C8—C9	−0.9 (2)
O1—C1—C2—C3	178.11 (15)	C8—N1—C7—C6	0.8 (2)
O1—C1—C8—N1	0.9 (2)	C8—C1—C2—C3	−1.3 (2)
O1—C1—C8—C9	−178.57 (13)	C9—C5—C6—C7	0.0 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C10/ C11/C11'–C13'/C14 and C11–C13/C14'/C10'/C11' rings, respectively, where primed atoms are related by the symmetry operation -x, 1 - y, 1 - z.

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2WA···O2ⁱⁱ	0.85	1.98	2.8239 (16)	176
O2W—H2WB···O3	0.85	2.02	2.8610 (15)	168
O1W—H1WA···O2	0.85	1.98	2.8150 (17)	169
O1W—H1WB···O4ⁱⁱⁱ	0.85	2.05	2.8806 (18)	166
O1—H1···O1W	0.82 (1)	1.84 (1)	2.6390 (16)	165 (2)
N1—H1A···O2W	0.87 (1)	1.89 (1)	2.7347 (18)	164 (2)
C6—H6···O3^iv	0.93	2.46	3.3153 (19)	154
C4—H4···O4^v	0.93	2.45	3.352 (2)	165
C14—H14···O1^vi	0.93	2.57	3.3173 (18)	137
C12—H12···O3	0.93	2.46	3.0439 (17)	121
C7—H7···Cg1ⁱⁱ	0.93	2.82	3.6125 (17)	144
C7—H7···Cg2^iv	0.93	2.82	3.6125 (17)	144

Symmetry codes: (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1, −y+1, −z; (vi) x−1, y, z.

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Bis(8-hy­droxy­quinolinium) naphthalene-1,5-di­sulfonate tetra­hydrate

Supporting information

Key indicators

checkCIF/PLATON results

Bis(8-hydroxyquinolinium) naphthalene-1,5-disulfonate tetrahydrate