The low-temperature triclinic crystal structure of silver 3-sulfo­benzoic acid

Bettinger, R.T.; Squattrito, P.J.; Aulakh, D.

doi:10.1107/S2056989020009408

The low-temperature triclinic crystal structure of silver 3-sulfobenzoic acid

R. T. Bettinger, P. J. Squattrito and D. Aulakh

Silver(I) 3-carboxybenzenesulfonate, Ag(O₃SC₆H₄CO₂H), has been found to undergo a reversible phase transition from monoclinic to triclinic between 160 and 150 K. The low-temperature triclinic structure (space group P $\overline{1}$ ) has been determined at 100 K.

Keywords: crystal structure; silver sulfonate salt; low temperature; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020009408/mw2166sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009408/mw2166Isup2.hkl Contains datablock I

CCDC reference: 2015332

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.023
wR factor = 0.057
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.68 Report
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C14 H10 Ag2 O10 S2

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Ag1       (I)       .       1.04 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Ag2       (I)       .       1.01 Info
PLAT804_ALERT_5_G Number of ARU-Code Packing Problem(s) in PLATON           1 Info
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          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 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
  12 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   5 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: CrystalMaker (Palmer, 2014).

Poly[(µ₄-3-carboxybenzenesulfonato)silver(I)] top

Crystal data top

[Ag(C₇H₅O₅S)]	Z = 4
M_r = 309.04	F(000) = 600
Triclinic, P1	D_x = 2.565 Mg m⁻³
a = 6.0376 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6293 (7) Å	Cell parameters from 5814 reflections
c = 15.5903 (12) Å	θ = 2.7–28.4°
α = 92.315 (1)°	µ = 2.77 mm⁻¹
β = 99.589 (1)°	T = 100 K
γ = 90.657 (1)°	Block, colorless
V = 800.12 (11) Å³	0.10 × 0.09 × 0.02 mm

Data collection top

Bruker APEXII CCD diffractometer	3464 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.019
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.4°, θ_min = 2.4°
T_min = 0.675, T_max = 0.746	h = −8→8
11343 measured reflections	k = −11→11
3990 independent reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.023	Hydrogen site location: difference Fourier map
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0312P)² + 0.7957P] where P = (F_o² + 2F_c²)/3
3990 reflections	(Δ/σ)_max = 0.002
255 parameters	Δρ_max = 1.46 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻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.

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

	x	y	z	U_iso*/U_eq
Ag1	1.38401 (3)	0.20362 (2)	0.54061 (2)	0.01134 (6)
Ag2	0.84468 (3)	0.29410 (2)	0.45908 (2)	0.01133 (6)
S1	1.30827 (10)	0.44688 (7)	0.38473 (4)	0.00764 (12)
S2	0.91114 (10)	0.05323 (7)	0.61650 (4)	0.00735 (12)
O1	0.8095 (3)	0.0907 (2)	0.04187 (13)	0.0171 (4)
O2	1.1825 (3)	0.1223 (2)	0.08315 (12)	0.0147 (4)
H2	1.186373	0.069042	0.037146	0.022*
O3	1.4157 (3)	0.5928 (2)	0.36958 (12)	0.0118 (4)
O4	1.1960 (3)	0.4580 (2)	0.46182 (12)	0.0113 (4)
O5	1.4577 (3)	0.3141 (2)	0.38907 (12)	0.0120 (4)
O6	1.0685 (3)	0.3705 (2)	0.92789 (12)	0.0151 (4)
O7	0.7208 (3)	0.4338 (2)	0.94908 (13)	0.0172 (4)
H7	0.792105	0.496134	0.986827	0.026*
O8	1.0577 (3)	0.1870 (2)	0.61036 (12)	0.0122 (4)
O9	1.0299 (3)	−0.0917 (2)	0.63142 (12)	0.0113 (4)
O10	0.7283 (3)	0.0403 (2)	0.54050 (12)	0.0121 (4)
C1	0.9468 (4)	0.2658 (3)	0.16077 (16)	0.0098 (5)
C2	1.1255 (4)	0.3040 (3)	0.22732 (16)	0.0089 (5)
H2A	1.269323	0.261007	0.226531	0.011*
C3	1.0903 (4)	0.4059 (3)	0.29493 (16)	0.0085 (5)
C4	0.8808 (4)	0.4739 (3)	0.29484 (17)	0.0098 (5)
H4	0.858595	0.544361	0.340934	0.012*
C5	0.7059 (4)	0.4378 (3)	0.22695 (17)	0.0113 (5)
H5	0.564694	0.485685	0.225963	0.014*
C6	0.7358 (4)	0.3320 (3)	0.16042 (17)	0.0122 (5)
H6	0.614232	0.304894	0.115096	0.015*
C7	0.9731 (4)	0.1514 (3)	0.08975 (17)	0.0114 (5)
C8	0.7557 (4)	0.2413 (3)	0.84027 (16)	0.0101 (5)
C9	0.8758 (4)	0.1989 (3)	0.77403 (16)	0.0089 (5)
H9	1.022664	0.239791	0.774347	0.011*
C10	0.7759 (4)	0.0954 (3)	0.70750 (16)	0.0083 (5)
C11	0.5641 (4)	0.0292 (3)	0.70888 (16)	0.0094 (5)
H11	0.498762	−0.043294	0.664035	0.011*
C12	0.4502 (4)	0.0705 (3)	0.77651 (17)	0.0109 (5)
H12	0.307895	0.024014	0.778523	0.013*
C13	0.5423 (4)	0.1791 (3)	0.84132 (17)	0.0116 (5)
H13	0.460534	0.210509	0.885891	0.014*
C14	0.8629 (4)	0.3547 (3)	0.91029 (16)	0.0104 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01230 (10)	0.00897 (10)	0.01265 (10)	−0.00049 (7)	0.00235 (7)	−0.00154 (7)
Ag2	0.01222 (10)	0.00908 (10)	0.01249 (10)	0.00046 (7)	0.00190 (7)	−0.00134 (7)
S1	0.0092 (3)	0.0059 (3)	0.0076 (3)	0.0002 (2)	0.0012 (2)	−0.0016 (2)
S2	0.0092 (3)	0.0058 (3)	0.0071 (3)	−0.0001 (2)	0.0017 (2)	−0.0015 (2)
O1	0.0147 (10)	0.0189 (10)	0.0160 (10)	0.0011 (7)	0.0001 (8)	−0.0103 (8)
O2	0.0149 (9)	0.0163 (10)	0.0122 (9)	0.0022 (7)	0.0015 (7)	−0.0069 (7)
O3	0.0131 (9)	0.0091 (9)	0.0124 (9)	−0.0021 (7)	−0.0005 (7)	0.0006 (7)
O4	0.0133 (9)	0.0128 (9)	0.0079 (8)	−0.0011 (7)	0.0025 (7)	−0.0014 (7)
O5	0.0121 (9)	0.0079 (8)	0.0151 (9)	0.0026 (7)	−0.0003 (7)	−0.0016 (7)
O6	0.0154 (10)	0.0156 (10)	0.0134 (9)	−0.0029 (7)	0.0011 (7)	−0.0046 (7)
O7	0.0188 (10)	0.0173 (10)	0.0150 (10)	−0.0009 (8)	0.0041 (8)	−0.0104 (8)
O8	0.0161 (9)	0.0067 (8)	0.0151 (9)	−0.0025 (7)	0.0070 (7)	−0.0017 (7)
O9	0.0132 (9)	0.0087 (8)	0.0128 (9)	0.0037 (7)	0.0049 (7)	−0.0006 (7)
O10	0.0126 (9)	0.0138 (9)	0.0090 (9)	0.0011 (7)	−0.0004 (7)	−0.0025 (7)
C1	0.0139 (12)	0.0069 (11)	0.0087 (11)	0.0001 (9)	0.0025 (9)	−0.0011 (9)
C2	0.0098 (12)	0.0071 (11)	0.0098 (11)	0.0011 (9)	0.0016 (9)	0.0001 (9)
C3	0.0093 (11)	0.0087 (11)	0.0071 (11)	−0.0002 (9)	0.0005 (9)	0.0006 (9)
C4	0.0124 (12)	0.0075 (11)	0.0096 (11)	−0.0002 (9)	0.0023 (9)	−0.0010 (9)
C5	0.0097 (12)	0.0105 (12)	0.0143 (12)	0.0020 (9)	0.0034 (9)	0.0018 (10)
C6	0.0125 (12)	0.0112 (12)	0.0119 (12)	−0.0018 (9)	−0.0004 (9)	0.0003 (9)
C7	0.0170 (13)	0.0092 (11)	0.0083 (12)	0.0014 (9)	0.0023 (9)	0.0011 (9)
C8	0.0127 (12)	0.0082 (11)	0.0087 (12)	0.0007 (9)	0.0000 (9)	−0.0002 (9)
C9	0.0087 (11)	0.0064 (11)	0.0112 (12)	−0.0002 (9)	0.0004 (9)	0.0012 (9)
C10	0.0097 (12)	0.0080 (11)	0.0072 (11)	0.0019 (9)	0.0018 (9)	−0.0015 (9)
C11	0.0117 (12)	0.0069 (11)	0.0091 (11)	0.0006 (9)	0.0005 (9)	0.0003 (9)
C12	0.0082 (11)	0.0112 (12)	0.0133 (12)	−0.0001 (9)	0.0020 (9)	0.0002 (9)
C13	0.0120 (12)	0.0131 (12)	0.0097 (12)	0.0013 (9)	0.0021 (9)	−0.0006 (9)
C14	0.0161 (13)	0.0093 (11)	0.0061 (11)	0.0004 (9)	0.0026 (9)	0.0004 (9)

Geometric parameters (Å, º) top

Ag1—O3ⁱ	2.3868 (18)	O7—C14	1.311 (3)
Ag1—O8	2.4091 (18)	O7—H7	0.8400
Ag1—O10ⁱⁱ	2.4406 (18)	C1—C2	1.393 (3)
Ag1—O10ⁱⁱⁱ	2.5249 (18)	C1—C6	1.402 (4)
Ag1—O5	2.6853 (19)	C1—C7	1.483 (3)
Ag1—O4	2.7254 (19)	C2—C3	1.390 (3)
Ag2—O9ⁱⁱ	2.4090 (17)	C2—H2A	0.9500
Ag2—O5^iv	2.4199 (18)	C3—C4	1.400 (3)
Ag2—O4^v	2.4609 (18)	C4—C5	1.388 (4)
Ag2—O4	2.5295 (18)	C4—H4	0.9500
Ag2—O8	2.6953 (19)	C5—C6	1.389 (4)
Ag2—O10	2.7179 (19)	C5—H5	0.9500
S1—O3	1.4556 (18)	C6—H6	0.9500
S1—O5	1.4629 (18)	C8—C13	1.393 (4)
S1—O4	1.4754 (18)	C8—C9	1.397 (3)
S1—C3	1.776 (3)	C8—C14	1.494 (3)
S2—O9	1.4560 (18)	C9—C10	1.393 (3)
S2—O8	1.4624 (18)	C9—H9	0.9500
S2—O10	1.4784 (19)	C10—C11	1.399 (3)
S2—C10	1.778 (2)	C11—C12	1.388 (3)
O1—C7	1.232 (3)	C11—H11	0.9500
O2—C7	1.312 (3)	C12—C13	1.390 (4)
O2—H2	0.8400	C12—H12	0.9500
O6—C14	1.231 (3)	C13—H13	0.9500

O3ⁱ—Ag1—O8	99.00 (6)	Ag1ⁱ—O3—Ag2^v	67.35 (4)
O3ⁱ—Ag1—O10ⁱⁱ	164.88 (6)	S1—O3—Ag2ⁱⁱⁱ	68.22 (7)
O8—Ag1—O10ⁱⁱ	89.93 (6)	Ag1ⁱ—O3—Ag2ⁱⁱⁱ	91.87 (5)
O3ⁱ—Ag1—O10ⁱⁱⁱ	93.71 (6)	Ag2^v—O3—Ag2ⁱⁱⁱ	105.51 (5)
O8—Ag1—O10ⁱⁱⁱ	134.17 (6)	S1—O4—Ag2^v	122.51 (10)
O10ⁱⁱ—Ag1—O10ⁱⁱⁱ	71.42 (7)	S1—O4—Ag2	117.62 (10)
O3ⁱ—Ag1—O5	95.65 (6)	Ag2^v—O4—Ag2	108.75 (7)
O8—Ag1—O5	133.72 (6)	S1—O4—Ag1	97.01 (9)
O10ⁱⁱ—Ag1—O5	86.75 (6)	Ag2^v—O4—Ag1	123.21 (7)
O10ⁱⁱⁱ—Ag1—O5	87.86 (6)	Ag2—O4—Ag1	80.66 (5)
O3ⁱ—Ag1—O4	79.09 (6)	S1—O4—Ag1ⁱ	68.13 (7)
O8—Ag1—O4	87.10 (6)	Ag2^v—O4—Ag1ⁱ	59.17 (4)
O10ⁱⁱ—Ag1—O4	113.75 (6)	Ag2—O4—Ag1ⁱ	164.54 (7)
O10ⁱⁱⁱ—Ag1—O4	138.66 (6)	Ag1—O4—Ag1ⁱ	113.67 (5)
O5—Ag1—O4	53.11 (5)	S1—O5—Ag2ⁱⁱⁱ	129.94 (11)
O9ⁱⁱ—Ag2—O5^iv	100.47 (6)	S1—O5—Ag1	99.04 (9)
O9ⁱⁱ—Ag2—O4^v	163.71 (6)	Ag2ⁱⁱⁱ—O5—Ag1	81.60 (5)
O5^iv—Ag2—O4^v	88.30 (6)	C14—O7—H7	109.5
O9ⁱⁱ—Ag2—O4	92.99 (6)	S2—O8—Ag1	129.24 (10)
O5^iv—Ag2—O4	134.11 (6)	S2—O8—Ag2	98.80 (9)
O4^v—Ag2—O4	71.25 (7)	Ag1—O8—Ag2	83.46 (6)
O9ⁱⁱ—Ag2—O8	95.18 (6)	S2—O9—Ag2ⁱⁱ	135.66 (11)
O5^iv—Ag2—O8	135.75 (6)	S2—O9—Ag1ⁱⁱ	79.15 (8)
O4^v—Ag2—O8	87.79 (6)	Ag2ⁱⁱ—O9—Ag1ⁱⁱ	68.49 (4)
O4—Ag2—O8	85.39 (6)	S2—O9—Ag1	68.85 (7)
O9ⁱⁱ—Ag2—O10	79.91 (6)	Ag2ⁱⁱ—O9—Ag1	90.55 (5)
O5^iv—Ag2—O10	89.29 (6)	Ag1ⁱⁱ—O9—Ag1	104.81 (5)
O4^v—Ag2—O10	114.18 (6)	S2—O10—Ag1ⁱⁱ	123.30 (10)
O4—Ag2—O10	136.43 (6)	S2—O10—Ag1^iv	118.98 (10)
O8—Ag2—O10	53.09 (5)	Ag1ⁱⁱ—O10—Ag1^iv	108.58 (7)
O3—S1—O5	113.96 (11)	S2—O10—Ag2	97.40 (9)
O3—S1—O4	112.15 (11)	Ag1ⁱⁱ—O10—Ag2	121.23 (7)
O5—S1—O4	110.84 (11)	Ag1^iv—O10—Ag2	79.11 (5)
O3—S1—C3	107.55 (11)	S2—O10—Ag2ⁱⁱ	67.58 (7)
O5—S1—C3	106.29 (11)	Ag1ⁱⁱ—O10—Ag2ⁱⁱ	59.96 (4)
O4—S1—C3	105.45 (11)	Ag1^iv—O10—Ag2ⁱⁱ	166.05 (7)
O3—S1—Ag1	134.18 (8)	Ag2—O10—Ag2ⁱⁱ	113.18 (5)
O5—S1—Ag1	54.60 (8)	C2—C1—C6	120.7 (2)
O4—S1—Ag1	56.24 (7)	C2—C1—C7	121.0 (2)
C3—S1—Ag1	118.27 (8)	C6—C1—C7	118.3 (2)
O3—S1—Ag2	142.49 (8)	C3—C2—C1	119.0 (2)
O5—S1—Ag2	101.87 (8)	C3—C2—H2A	120.5
C3—S1—Ag2	70.67 (8)	C1—C2—H2A	120.5
Ag1—S1—Ag2	60.743 (12)	C2—C3—C4	120.7 (2)
O3—S1—Ag2^v	75.89 (8)	C2—C3—S1	120.38 (19)
O5—S1—Ag2^v	133.57 (8)	C4—C3—S1	118.86 (19)
C3—S1—Ag2^v	113.59 (8)	C2—C3—Ag2	122.32 (16)
Ag1—S1—Ag2^v	85.217 (16)	C4—C3—Ag2	67.59 (14)
Ag2—S1—Ag2^v	71.389 (13)	S1—C3—Ag2	79.16 (8)
O3—S1—Ag2ⁱⁱⁱ	89.34 (8)	C5—C4—C3	119.5 (2)
O4—S1—Ag2ⁱⁱⁱ	105.55 (8)	C5—C4—Ag2	112.49 (17)
C3—S1—Ag2ⁱⁱⁱ	135.36 (8)	C3—C4—Ag2	87.60 (15)
Ag1—S1—Ag2ⁱⁱⁱ	58.742 (11)	C5—C4—H4	120.2
Ag2—S1—Ag2ⁱⁱⁱ	118.903 (18)	C3—C4—H4	120.2
Ag2^v—S1—Ag2ⁱⁱⁱ	110.509 (17)	Ag2—C4—H4	70.2
O5—S1—Ag1ⁱ	110.81 (8)	C4—C5—C6	120.5 (2)
O4—S1—Ag1ⁱ	89.35 (7)	C4—C5—Ag2	47.98 (13)
C3—S1—Ag1ⁱ	131.60 (8)	C6—C5—Ag2	116.08 (17)
Ag1—S1—Ag1ⁱ	108.357 (17)	C4—C5—H5	119.7
Ag2—S1—Ag1ⁱ	127.793 (18)	C6—C5—H5	119.7
Ag2^v—S1—Ag1ⁱ	56.515 (11)	Ag2—C5—H5	103.4
Ag2ⁱⁱⁱ—S1—Ag1ⁱ	79.804 (14)	C5—C6—C1	119.4 (2)
O9—S2—O8	114.02 (11)	C5—C6—H6	120.3
O9—S2—O10	112.31 (11)	C1—C6—H6	120.3
O8—S2—O10	110.71 (11)	O1—C7—O2	124.1 (2)
O9—S2—C10	107.87 (11)	O1—C7—C1	121.7 (2)
O8—S2—C10	106.02 (11)	O2—C7—C1	114.2 (2)
O10—S2—C10	105.29 (11)	C13—C8—C9	120.9 (2)
O9—S2—Ag2	134.36 (8)	C13—C8—C14	120.9 (2)
O8—S2—Ag2	54.86 (8)	C9—C8—C14	118.2 (2)
O10—S2—Ag2	55.85 (8)	C10—C9—C8	118.7 (2)
C10—S2—Ag2	117.76 (8)	C10—C9—H9	120.6
O9—S2—Ag1ⁱⁱ	76.58 (8)	C8—C9—H9	120.6
O8—S2—Ag1ⁱⁱ	132.19 (8)	C9—C10—C11	120.9 (2)
C10—S2—Ag1ⁱⁱ	114.74 (8)	C9—C10—S2	120.11 (19)
Ag2—S2—Ag1ⁱⁱ	83.690 (15)	C11—C10—S2	118.95 (19)
O9—S2—Ag1^iv	142.72 (8)	C9—C10—Ag1^iv	122.76 (16)
O8—S2—Ag1^iv	101.22 (8)	C11—C10—Ag1^iv	67.27 (14)
C10—S2—Ag1^iv	71.67 (8)	S2—C10—Ag1^iv	78.38 (8)
Ag2—S2—Ag1^iv	59.268 (11)	C12—C11—C10	119.3 (2)
Ag1ⁱⁱ—S2—Ag1^iv	70.705 (13)	C12—C11—Ag1^iv	111.71 (16)
O9—S2—Ag1	88.47 (8)	C10—C11—Ag1^iv	88.31 (15)
O10—S2—Ag1	106.42 (8)	C12—C11—H11	120.4
C10—S2—Ag1	135.01 (8)	C10—C11—H11	120.4
Ag2—S2—Ag1	60.142 (11)	Ag1^iv—C11—H11	70.3
Ag1ⁱⁱ—S2—Ag1	109.706 (17)	C11—C12—C13	120.7 (2)
Ag1^iv—S2—Ag1	118.896 (18)	C11—C12—Ag1^iv	48.75 (13)
O8—S2—Ag2ⁱⁱ	109.90 (8)	C13—C12—Ag1^iv	116.17 (17)
O10—S2—Ag2ⁱⁱ	90.09 (7)	C11—C12—H12	119.6
C10—S2—Ag2ⁱⁱ	132.48 (8)	C13—C12—H12	119.6
Ag2—S2—Ag2ⁱⁱ	108.167 (17)	Ag1^iv—C12—H12	102.7
Ag1ⁱⁱ—S2—Ag2ⁱⁱ	57.481 (11)	C12—C13—C8	119.4 (2)
Ag1^iv—S2—Ag2ⁱⁱ	128.036 (18)	C12—C13—H13	120.3
Ag1—S2—Ag2ⁱⁱ	78.344 (13)	C8—C13—H13	120.3
C7—O2—H2	109.5	O6—C14—O7	124.4 (2)
S1—O3—Ag1ⁱ	135.48 (11)	O6—C14—C8	121.1 (2)
S1—O3—Ag2^v	79.83 (8)	O7—C14—C8	114.6 (2)

C6—C1—C2—C3	1.7 (4)	C13—C8—C9—C10	1.5 (4)
C7—C1—C2—C3	−176.8 (2)	C14—C8—C9—C10	−178.8 (2)
C1—C2—C3—C4	−2.3 (4)	C8—C9—C10—C11	−3.1 (4)
C1—C2—C3—S1	175.60 (19)	C8—C9—C10—S2	173.79 (19)
C1—C2—C3—Ag2	79.1 (3)	C8—C9—C10—Ag1^iv	78.3 (3)
O3—S1—C3—C2	98.3 (2)	O9—S2—C10—C9	98.0 (2)
O5—S1—C3—C2	−24.1 (2)	O8—S2—C10—C9	−24.5 (2)
O4—S1—C3—C2	−141.8 (2)	O10—S2—C10—C9	−141.9 (2)
Ag1—S1—C3—C2	−82.2 (2)	Ag2—S2—C10—C9	−82.8 (2)
Ag2—S1—C3—C2	−121.2 (2)	Ag1ⁱⁱ—S2—C10—C9	−178.88 (17)
Ag2^v—S1—C3—C2	−179.76 (17)	Ag1^iv—S2—C10—C9	−121.3 (2)
Ag2ⁱⁱⁱ—S1—C3—C2	−9.3 (3)	Ag1—S2—C10—C9	−8.4 (3)
Ag1ⁱ—S1—C3—C2	114.91 (19)	Ag2ⁱⁱ—S2—C10—C9	113.49 (19)
O3—S1—C3—C4	−83.7 (2)	O9—S2—C10—C11	−85.1 (2)
O5—S1—C3—C4	153.9 (2)	O8—S2—C10—C11	152.4 (2)
O4—S1—C3—C4	36.1 (2)	O10—S2—C10—C11	35.0 (2)
Ag1—S1—C3—C4	95.7 (2)	Ag2—S2—C10—C11	94.1 (2)
Ag2—S1—C3—C4	56.71 (19)	Ag1ⁱⁱ—S2—C10—C11	−2.0 (2)
Ag2^v—S1—C3—C4	−1.8 (2)	Ag1^iv—S2—C10—C11	55.63 (18)
Ag2ⁱⁱⁱ—S1—C3—C4	168.65 (14)	Ag1—S2—C10—C11	168.49 (14)
Ag1ⁱ—S1—C3—C4	−67.1 (2)	Ag2ⁱⁱ—S2—C10—C11	−69.6 (2)
O3—S1—C3—Ag2	−140.42 (9)	O9—S2—C10—Ag1^iv	−140.70 (9)
O5—S1—C3—Ag2	97.16 (9)	O8—S2—C10—Ag1^iv	96.78 (9)
O4—S1—C3—Ag2	−20.57 (9)	O10—S2—C10—Ag1^iv	−20.60 (9)
Ag1—S1—C3—Ag2	39.04 (7)	Ag2—S2—C10—Ag1^iv	38.49 (7)
Ag2^v—S1—C3—Ag2	−58.52 (6)	Ag1ⁱⁱ—S2—C10—Ag1^iv	−57.59 (6)
Ag2ⁱⁱⁱ—S1—C3—Ag2	111.94 (8)	Ag1—S2—C10—Ag1^iv	112.87 (8)
Ag1ⁱ—S1—C3—Ag2	−123.85 (7)	Ag2ⁱⁱ—S2—C10—Ag1^iv	−125.22 (7)
C2—C3—C4—C5	0.7 (4)	C9—C10—C11—C12	1.6 (4)
S1—C3—C4—C5	−177.23 (19)	S2—C10—C11—C12	−175.29 (19)
Ag2—C3—C4—C5	−114.6 (2)	Ag1^iv—C10—C11—C12	−114.1 (2)
C2—C3—C4—Ag2	115.3 (2)	C9—C10—C11—Ag1^iv	115.7 (2)
S1—C3—C4—Ag2	−62.63 (17)	S2—C10—C11—Ag1^iv	−61.23 (17)
C3—C4—C5—C6	1.5 (4)	C10—C11—C12—C13	1.5 (4)
Ag2—C4—C5—C6	−99.0 (2)	Ag1^iv—C11—C12—C13	−99.3 (2)
C3—C4—C5—Ag2	100.5 (3)	C10—C11—C12—Ag1^iv	100.8 (3)
C4—C5—C6—C1	−2.1 (4)	C11—C12—C13—C8	−3.0 (4)
Ag2—C5—C6—C1	−56.9 (3)	Ag1^iv—C12—C13—C8	−58.8 (3)
C2—C1—C6—C5	0.5 (4)	C9—C8—C13—C12	1.5 (4)
C7—C1—C6—C5	179.0 (2)	C14—C8—C13—C12	−178.2 (2)
C2—C1—C7—O1	163.7 (3)	C13—C8—C14—O6	155.1 (2)
C6—C1—C7—O1	−14.8 (4)	C9—C8—C14—O6	−24.6 (4)
C2—C1—C7—O2	−16.4 (3)	C13—C8—C14—O7	−25.5 (3)
C6—C1—C7—O2	165.0 (2)	C9—C8—C14—O7	154.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^vi	0.84	1.81	2.631 (3)	164
O7—H7···O6^vii	0.84	1.81	2.651 (3)	176
C4—H4···O8^v	0.95	2.43	3.214 (3)	140
C11—H11···O5ⁱⁱ	0.95	2.48	3.269 (3)	141

Symmetry codes: (ii) −x+2, −y, −z+1; (v) −x+2, −y+1, −z+1; (vi) −x+2, −y, −z; (vii) −x+2, −y+1, −z+2.

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The low-temperature triclinic crystal structure of silver 3-sulfo­benzoic acid

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The low-temperature triclinic crystal structure of silver 3-sulfobenzoic acid