2-Amino-6-chloro­pyridinium 3-carb­oxy-4-hy­droxy­benzene­sulfonate

Manickam, R.; Rajakannan, V.; Prabhaharan, M.; Srinivasan, G.

doi:10.1107/S2414314619005662

2-Amino-6-chloropyridinium 3-carboxy-4-hydroxybenzenesulfonate

R. Manickam, V. Rajakannan, M. Prabhaharan and G. Srinivasan

In the 3-carboxy-4-hydroxybenzenesulfonate anion of the title salt, C₅H₆ClN₂⁺·C₇H₅O₆S⁻, an intramolecular O—H

O hydrogen bond with an S(6) ring motif is observed. In the crystal, the anions are linked into a chain structure running along [1 $\overline{1}$ 0] via an O—H

O hydrogen bond formed between the carboxy and sulfonate groups. The 2-amino-6-chloropyridinium cations bridge the anion chains via N—H

O and C—H

O hydrogen bonds, forming a sheet parallel to the ab plane. In the sheet, a C—H

Cl interaction between the cations is also observed.

Keywords: crystal structure; hydrogen bond; 2-amino-6-chloropyridinium; 3-carboxy-4-hydroxybenzenesulfonate.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619005662/is4031sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314619005662/is4031Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619005662/is4031Isup3.cml Supplementary material

CCDC reference: 1912046

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R factor = 0.028
wR factor = 0.079
Data-to-parameter ratio = 30.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.201 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

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

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

2-Amino-6-chloropyridinium 3-carboxy-4-hydroxybenzenesulfonate top

Crystal data top

C₅H₆ClN₂⁺·C₇H₅O₆S⁻	F(000) = 1424
M_r = 346.74	D_x = 1.642 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9829 reflections
a = 16.0043 (3) Å	θ = 2.6–37.6°
b = 7.4649 (2) Å	µ = 0.45 mm⁻¹
c = 23.5799 (5) Å	T = 100 K
β = 95.161 (1)°	Block, colourless
V = 2805.68 (11) Å³	0.39 × 0.28 × 0.21 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area detector diffractometer	7386 independent reflections
Radiation source: fine-focus sealed tube	6997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
φ and ω scans	θ_max = 37.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
T_min = 0.842, T_max = 0.911	k = −11→12
26502 measured reflections	l = −40→27

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	All H-atom parameters refined
S = 1.14	w = 1/[σ²(F_o²) + (0.0359P)² + 1.5791P] where P = (F_o² + 2F_c²)/3
7386 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat [Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107] operating at 100.0 (1) K.

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. 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 > 2sigma(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.

All H atoms were located in a difference Fourier map and allowed to refine freely [N—H = 0.849 (14)–0.890 (15) Å, O—H = 0.850 (16)–0.870 (17) Å and C—H = 0.931 (14)–0.987 (13) Å].

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

	x	y	z	U_iso*/U_eq
S1	0.194955 (9)	0.60531 (2)	0.120818 (6)	0.01019 (3)
O1	−0.11147 (3)	0.84652 (9)	0.08056 (2)	0.01856 (10)
O2	−0.14331 (3)	0.87680 (8)	−0.01363 (2)	0.01719 (10)
O3	−0.03230 (4)	0.78169 (9)	−0.08199 (2)	0.01771 (10)
O4	0.24938 (3)	0.76081 (8)	0.12876 (2)	0.01497 (9)
O5	0.14455 (3)	0.57579 (7)	0.16888 (2)	0.01358 (8)
O6	0.24046 (3)	0.44196 (7)	0.10735 (2)	0.01408 (8)
C6	0.04546 (4)	0.71656 (9)	0.06802 (3)	0.01147 (9)
C7	0.12440 (4)	0.64976 (9)	0.06087 (3)	0.01058 (9)
C8	0.15093 (4)	0.62660 (9)	0.00621 (3)	0.01268 (10)
C9	0.09758 (4)	0.67148 (10)	−0.04112 (3)	0.01408 (10)
C10	0.01735 (4)	0.73936 (9)	−0.03450 (3)	0.01221 (10)
C11	−0.00912 (4)	0.76231 (9)	0.02035 (3)	0.01131 (9)
C12	−0.09384 (4)	0.83327 (9)	0.02688 (3)	0.01288 (10)
N1	0.13605 (4)	0.27027 (8)	0.23152 (3)	0.01344 (9)
N2	0.19616 (4)	0.11253 (9)	0.16085 (3)	0.01786 (11)
Cl1	0.079291 (13)	0.48895 (2)	0.305211 (8)	0.01915 (4)
C1	0.09741 (4)	0.27792 (9)	0.28073 (3)	0.01322 (10)
C2	0.07675 (5)	0.12856 (10)	0.30926 (3)	0.01542 (11)
C3	0.09926 (5)	−0.03714 (10)	0.28634 (3)	0.01780 (12)
C4	0.13957 (5)	−0.04791 (10)	0.23772 (3)	0.01718 (12)
C5	0.15832 (4)	0.11192 (9)	0.20889 (3)	0.01376 (10)
H2	0.0514 (8)	0.1360 (19)	0.3432 (6)	0.021 (3)*
H3	0.0891 (10)	−0.145 (2)	0.3046 (7)	0.032 (4)*
H4	0.1526 (8)	−0.1600 (19)	0.2225 (6)	0.023 (3)*
H6	0.0274 (8)	0.7370 (19)	0.1064 (6)	0.019 (3)*
H8	0.2071 (8)	0.5821 (17)	0.0021 (5)	0.015 (3)*
H9	0.1142 (9)	0.656 (2)	−0.0780 (6)	0.024 (3)*
H1O1	−0.1623 (11)	0.888 (2)	0.0808 (7)	0.041 (4)*
H1O3	−0.0781 (10)	0.820 (2)	−0.0709 (7)	0.032 (4)*
H1N1	0.1436 (8)	0.3713 (18)	0.2134 (6)	0.019 (3)*
H1N2	0.2102 (9)	0.215 (2)	0.1449 (6)	0.028 (4)*
H2N2	0.2116 (9)	0.0121 (19)	0.1485 (6)	0.023 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.00848 (6)	0.01208 (6)	0.01013 (6)	0.00212 (4)	0.00147 (4)	−0.00012 (4)
O1	0.01210 (19)	0.0300 (3)	0.0140 (2)	0.00791 (19)	0.00350 (16)	0.00012 (19)
O2	0.01249 (19)	0.0226 (3)	0.0160 (2)	0.00428 (17)	−0.00103 (16)	0.00197 (18)
O3	0.0150 (2)	0.0267 (3)	0.01119 (19)	0.00370 (19)	−0.00049 (16)	0.00279 (18)
O4	0.01189 (18)	0.0154 (2)	0.0174 (2)	−0.00116 (16)	0.00033 (15)	−0.00181 (17)
O5	0.01388 (19)	0.0164 (2)	0.01106 (18)	0.00364 (16)	0.00411 (15)	0.00170 (15)
O6	0.01187 (18)	0.0148 (2)	0.0160 (2)	0.00497 (16)	0.00341 (15)	0.00015 (16)
C6	0.0094 (2)	0.0145 (2)	0.0107 (2)	0.00190 (18)	0.00201 (17)	0.00037 (18)
C7	0.0090 (2)	0.0127 (2)	0.0102 (2)	0.00151 (17)	0.00168 (16)	−0.00005 (18)
C8	0.0110 (2)	0.0160 (3)	0.0115 (2)	0.00172 (19)	0.00298 (17)	−0.00057 (19)
C9	0.0128 (2)	0.0192 (3)	0.0105 (2)	0.0021 (2)	0.00293 (18)	−0.0003 (2)
C10	0.0115 (2)	0.0147 (2)	0.0104 (2)	0.00023 (19)	0.00100 (17)	0.00095 (18)
C11	0.0092 (2)	0.0137 (2)	0.0112 (2)	0.00139 (18)	0.00165 (17)	0.00063 (18)
C12	0.0102 (2)	0.0148 (3)	0.0137 (2)	0.00172 (19)	0.00169 (18)	0.00027 (19)
N1	0.0151 (2)	0.0119 (2)	0.0135 (2)	0.00114 (17)	0.00169 (17)	0.00032 (17)
N2	0.0211 (3)	0.0158 (3)	0.0177 (2)	0.0036 (2)	0.0074 (2)	0.0010 (2)
Cl1	0.02752 (9)	0.01356 (7)	0.01658 (7)	0.00355 (6)	0.00307 (6)	−0.00200 (5)
C1	0.0145 (2)	0.0129 (2)	0.0120 (2)	0.00098 (19)	−0.00034 (18)	−0.00142 (19)
C2	0.0197 (3)	0.0146 (3)	0.0119 (2)	−0.0017 (2)	0.0009 (2)	−0.0006 (2)
C3	0.0260 (3)	0.0134 (3)	0.0142 (3)	−0.0020 (2)	0.0023 (2)	0.0003 (2)
C4	0.0236 (3)	0.0126 (3)	0.0155 (3)	0.0008 (2)	0.0027 (2)	−0.0003 (2)
C5	0.0145 (2)	0.0132 (2)	0.0136 (2)	0.00182 (19)	0.00097 (19)	−0.00013 (19)

Geometric parameters (Å, º) top

S1—O4	1.4532 (6)	C10—C11	1.4072 (9)
S1—O5	1.4656 (5)	C11—C12	1.4765 (9)
S1—O6	1.4696 (5)	N1—C5	1.3577 (9)
S1—C7	1.7595 (6)	N1—C1	1.3643 (9)
O1—C12	1.3252 (9)	N1—H1N1	0.881 (14)
O1—H1O1	0.870 (17)	N2—C5	1.3317 (9)
O2—C12	1.2283 (8)	N2—H1N2	0.890 (15)
O3—C10	1.3509 (8)	N2—H2N2	0.849 (14)
O3—H1O3	0.850 (16)	Cl1—C1	1.7115 (7)
C6—C7	1.3824 (9)	C1—C2	1.3583 (10)
C6—C11	1.4024 (9)	C2—C3	1.4095 (11)
C6—H6	0.987 (13)	C2—H2	0.931 (14)
C7—C8	1.4036 (9)	C3—C4	1.3676 (11)
C8—C9	1.3840 (9)	C3—H3	0.932 (17)
C8—H8	0.972 (13)	C4—C5	1.4186 (10)
C9—C10	1.4020 (9)	C4—H4	0.941 (14)
C9—H9	0.939 (14)

O4—S1—O5	112.69 (3)	C10—C11—C12	119.65 (6)
O4—S1—O6	112.81 (3)	O2—C12—O1	123.05 (6)
O5—S1—O6	111.12 (3)	O2—C12—C11	123.20 (6)
O4—S1—C7	106.66 (3)	O1—C12—C11	113.75 (6)
O5—S1—C7	106.94 (3)	C5—N1—C1	121.72 (6)
O6—S1—C7	106.12 (3)	C5—N1—H1N1	120.1 (9)
C12—O1—H1O1	108.1 (11)	C1—N1—H1N1	118.1 (9)
C10—O3—H1O3	106.5 (11)	C5—N2—H1N2	121.0 (10)
C7—C6—C11	120.03 (6)	C5—N2—H2N2	117.2 (9)
C7—C6—H6	120.9 (8)	H1N2—N2—H2N2	121.3 (13)
C11—C6—H6	119.0 (8)	C2—C1—N1	122.41 (6)
C6—C7—C8	120.77 (6)	C2—C1—Cl1	122.16 (5)
C6—C7—S1	119.84 (5)	N1—C1—Cl1	115.40 (5)
C8—C7—S1	119.29 (5)	C1—C2—C3	116.65 (7)
C9—C8—C7	119.68 (6)	C1—C2—H2	121.4 (9)
C9—C8—H8	120.8 (7)	C3—C2—H2	121.9 (9)
C7—C8—H8	119.5 (7)	C4—C3—C2	121.94 (7)
C8—C9—C10	120.16 (6)	C4—C3—H3	116.9 (10)
C8—C9—H9	120.8 (9)	C2—C3—H3	121.2 (10)
C10—C9—H9	119.0 (9)	C3—C4—C5	119.23 (7)
O3—C10—C9	117.94 (6)	C3—C4—H4	120.6 (9)
O3—C10—C11	122.00 (6)	C5—C4—H4	120.1 (9)
C9—C10—C11	120.05 (6)	N2—C5—N1	119.14 (6)
C6—C11—C10	119.32 (6)	N2—C5—C4	122.85 (7)
C6—C11—C12	121.03 (6)	N1—C5—C4	118.01 (6)

C11—C6—C7—C8	−0.09 (10)	O3—C10—C11—C12	0.52 (10)
C11—C6—C7—S1	176.17 (5)	C9—C10—C11—C12	−179.78 (6)
O4—S1—C7—C6	−96.71 (6)	C6—C11—C12—O2	179.20 (7)
O5—S1—C7—C6	24.08 (6)	C10—C11—C12—O2	−1.06 (11)
O6—S1—C7—C6	142.77 (6)	C6—C11—C12—O1	−0.49 (10)
O4—S1—C7—C8	79.60 (6)	C10—C11—C12—O1	179.25 (6)
O5—S1—C7—C8	−159.60 (5)	C5—N1—C1—C2	−1.85 (10)
O6—S1—C7—C8	−40.91 (6)	C5—N1—C1—Cl1	176.41 (5)
C6—C7—C8—C9	0.15 (10)	N1—C1—C2—C3	1.66 (10)
S1—C7—C8—C9	−176.13 (6)	Cl1—C1—C2—C3	−176.49 (6)
C7—C8—C9—C10	−0.15 (11)	C1—C2—C3—C4	−0.26 (11)
C8—C9—C10—O3	179.81 (7)	C2—C3—C4—C5	−0.94 (12)
C8—C9—C10—C11	0.10 (11)	C1—N1—C5—N2	−179.76 (7)
C7—C6—C11—C10	0.03 (10)	C1—N1—C5—C4	0.55 (10)
C7—C6—C11—C12	179.77 (6)	C3—C4—C5—N2	−178.87 (7)
O3—C10—C11—C6	−179.74 (6)	C3—C4—C5—N1	0.80 (11)
C9—C10—C11—C6	−0.04 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O6ⁱ	0.871 (17)	1.775 (17)	2.6061 (7)	158.7 (16)
O3—H1O3···O2	0.850 (16)	1.829 (16)	2.6027 (8)	150.5 (16)
N1—H1N1···O5	0.881 (14)	1.854 (14)	2.7272 (8)	171.4 (13)
N2—H1N2···O6	0.890 (15)	1.992 (15)	2.8814 (8)	178.6 (15)
N2—H2N2···O4ⁱⁱ	0.849 (14)	2.038 (14)	2.8823 (9)	173.1 (14)
C2—H2···O3ⁱⁱⁱ	0.931 (14)	2.389 (14)	3.2978 (9)	165.2 (12)
C3—H3···Cl1ⁱⁱ	0.934 (15)	2.737 (15)	3.5834 (8)	151.1 (13)
C4—H4···O5ⁱⁱ	0.941 (14)	2.340 (14)	3.2489 (9)	162.2 (11)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, y−1, z; (iii) x, −y+1, z+1/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

2-Amino-6-chloro­pyridinium 3-carb­oxy-4-hy­droxy­benzene­sulfonate

Supporting information

Key indicators

checkCIF/PLATON results

2-Amino-6-chloropyridinium 3-carboxy-4-hydroxybenzenesulfonate