2-Hydroxy­propanammonium benzene­thiol­ate

The asymmetric unit of the title compund, C₃H₁₀NO⁺·C₆H₅S⁻, contains two benzeno­thiol­ate anions and two 2-hydroxypropanammonium cations. The ions are linked into sheets of R₂⁴(8), R₂⁴(11) and R₂⁴(14) rings by a combination of N—H...S, O—H...S and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.084
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    -   C11     ..      10.00 su

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.25
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.04

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS Software (Stoe & Cie, 1999); cell refinement: IPDS Software; data reduction: X-RED32 (Stoe & Cie, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Hydroxypropanaminium benzenethiolate

Crystal data

C3H10NO^+·C6H5S^−	F(000) = 800
Mr = 185.28	Dx = 1.159 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5002 reflections
a = 13.226 (3) Å	θ = 2–30°
b = 9.182 (2) Å	µ = 0.26 mm^−1
c = 18.256 (4) Å	T = 200 K
β = 106.68 (3)°	Prism, colourless
V = 2123.7 (9) Å^3	0.21 × 0.18 × 0.15 mm
Z = 8

Data collection

Stoe IPDS diffractometer	2836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 25.1°, θmin = 2.2°
φ scans	h = −15→15
14929 measured reflections	k = −10→10
3762 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0532P)^2] where P = (Fo^2 + 2Fc^2)/3
3762 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.44 e Å^−3
6 restraints	Δρmin = −0.19 e Å^−3

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
S1	0.55642 (3)	0.26525 (5)	0.48603 (2)	0.03220 (12)
C1	0.66699 (12)	0.27626 (18)	0.44923 (10)	0.0303 (4)
C2	0.76346 (15)	0.2121 (2)	0.48711 (11)	0.0447 (5)
H2	0.7706	0.1602	0.5333	0.054*
C3	0.84903 (16)	0.2236 (3)	0.45786 (13)	0.0592 (6)
H3	0.9142	0.179	0.4842	0.071*
C4	0.84072 (16)	0.2991 (3)	0.39081 (13)	0.0600 (6)
H4	0.8999	0.3078	0.3714	0.072*
C5	0.74590 (16)	0.3612 (3)	0.35269 (12)	0.0550 (6)
H5	0.7392	0.4123	0.3063	0.066*
C6	0.65961 (14)	0.3501 (2)	0.38137 (10)	0.0409 (4)
H6	0.5945	0.3937	0.3542	0.049*
S2	0.31103 (4)	0.54986 (5)	0.21648 (3)	0.04118 (14)
C7	0.40203 (14)	0.42454 (19)	0.19694 (9)	0.0345 (4)
C8	0.48358 (15)	0.4723 (2)	0.16804 (11)	0.0417 (4)
H8	0.4896	0.5732	0.1587	0.05*
C9	0.55568 (17)	0.3763 (2)	0.15266 (13)	0.0544 (5)
H9	0.6101	0.4124	0.1332	0.065*
C10	0.54940 (19)	0.2300 (3)	0.16522 (13)	0.0594 (6)
H10	0.5988	0.1644	0.1544	0.071*
C11	0.4701 (2)	0.1799 (2)	0.19385 (13)	0.0590 (6)
H11	0.4653	0.0786	0.2031	0.071*
C12	0.39651 (17)	0.2753 (2)	0.20963 (11)	0.0475 (5)
H12	0.3424	0.2382	0.2291	0.057*
O1	0.70506 (10)	0.80163 (14)	0.55138 (8)	0.0486 (3)
H1O	0.7427	0.8354	0.593	0.073*
N1	0.64412 (12)	0.52911 (17)	0.60518 (9)	0.0365 (4)
C13	0.75095 (14)	0.5590 (2)	0.59888 (12)	0.0438 (5)
H13A	0.7833	0.4668	0.5887	0.053*
H13B	0.7954	0.5987	0.648	0.053*
C14	0.74789 (16)	0.6653 (2)	0.53615 (12)	0.0493 (5)
H14	0.7004	0.6251	0.4874	0.059*
C15	0.85789 (18)	0.6861 (3)	0.52582 (15)	0.0736 (8)
H15A	0.9074	0.716	0.5745	0.11*
H15B	0.8549	0.7615	0.4872	0.11*
H15C	0.8818	0.5942	0.509	0.11*
O2	0.45527 (10)	0.82859 (13)	0.25892 (7)	0.0423 (3)
H2O	0.4178	0.7535	0.2474	0.063*
N2	0.44153 (12)	0.98181 (17)	0.38824 (9)	0.0348 (3)
C16	0.54436 (13)	0.94344 (19)	0.37537 (10)	0.0351 (4)
H16A	0.5982	0.9301	0.4253	0.042*
H16B	0.5677	1.0242	0.3481	0.042*
C17	0.53516 (13)	0.80497 (19)	0.32884 (10)	0.0331 (4)
H17	0.5138	0.7229	0.3572	0.04*
C18	0.63971 (16)	0.7689 (3)	0.31457 (12)	0.0538 (5)
H18A	0.6613	0.8499	0.2874	0.081*
H18B	0.6321	0.6804	0.2835	0.081*
H18C	0.6934	0.7532	0.3636	0.081*
H1A	0.6117 (15)	0.4576 (17)	0.5727 (10)	0.051 (6)*
H1B	0.6513 (18)	0.505 (3)	0.6551 (7)	0.070 (7)*
H1C	0.6012 (14)	0.6068 (16)	0.5922 (12)	0.052 (6)*
H2A	0.3869 (11)	0.980 (2)	0.3451 (8)	0.050 (6)*
H2B	0.4272 (17)	0.9142 (19)	0.4198 (11)	0.060 (7)*
H2C	0.4455 (16)	1.0697 (14)	0.4110 (11)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0293 (2)	0.0321 (2)	0.0347 (2)	0.00058 (17)	0.00852 (18)	−0.00081 (19)
C1	0.0266 (8)	0.0307 (8)	0.0312 (9)	0.0001 (7)	0.0046 (7)	−0.0076 (7)
C2	0.0364 (10)	0.0556 (12)	0.0373 (10)	0.0099 (9)	0.0030 (8)	0.0019 (9)
C3	0.0287 (10)	0.0885 (17)	0.0562 (14)	0.0190 (11)	0.0054 (10)	−0.0027 (12)
C4	0.0356 (11)	0.0962 (18)	0.0529 (13)	0.0078 (11)	0.0201 (10)	−0.0054 (12)
C5	0.0473 (12)	0.0820 (16)	0.0395 (11)	0.0062 (11)	0.0185 (10)	0.0073 (11)
C6	0.0312 (9)	0.0551 (12)	0.0342 (10)	0.0081 (8)	0.0060 (8)	0.0033 (9)
S2	0.0340 (2)	0.0493 (3)	0.0376 (3)	−0.0068 (2)	0.0061 (2)	−0.0022 (2)
C7	0.0374 (9)	0.0343 (9)	0.0250 (9)	−0.0078 (8)	−0.0017 (8)	−0.0004 (7)
C8	0.0451 (11)	0.0365 (10)	0.0427 (11)	−0.0032 (8)	0.0113 (9)	0.0030 (8)
C9	0.0531 (13)	0.0558 (13)	0.0555 (13)	0.0046 (10)	0.0173 (11)	0.0014 (11)
C10	0.0646 (15)	0.0523 (13)	0.0551 (14)	0.0122 (11)	0.0072 (12)	−0.0044 (11)
C11	0.0793 (16)	0.0317 (10)	0.0473 (13)	0.0014 (11)	−0.0117 (12)	0.0020 (9)
C12	0.0559 (12)	0.0423 (11)	0.0354 (10)	−0.0161 (10)	−0.0011 (9)	0.0053 (9)
O1	0.0389 (7)	0.0440 (8)	0.0566 (9)	−0.0043 (6)	0.0034 (7)	0.0113 (7)
N1	0.0373 (8)	0.0298 (8)	0.0373 (9)	−0.0001 (7)	0.0028 (8)	0.0005 (7)
C13	0.0355 (10)	0.0428 (11)	0.0480 (12)	0.0032 (8)	0.0035 (9)	−0.0065 (9)
C14	0.0424 (11)	0.0668 (14)	0.0386 (11)	−0.0076 (10)	0.0115 (9)	−0.0062 (10)
C15	0.0521 (14)	0.111 (2)	0.0658 (16)	−0.0184 (14)	0.0299 (13)	−0.0199 (15)
O2	0.0479 (8)	0.0339 (7)	0.0341 (7)	−0.0022 (6)	−0.0057 (6)	−0.0012 (6)
N2	0.0377 (9)	0.0314 (8)	0.0308 (8)	0.0026 (7)	0.0025 (7)	−0.0008 (7)
C16	0.0329 (9)	0.0404 (10)	0.0283 (9)	−0.0064 (8)	0.0028 (8)	−0.0009 (8)
C17	0.0322 (9)	0.0368 (9)	0.0278 (9)	−0.0003 (7)	0.0043 (8)	0.0037 (7)
C18	0.0436 (11)	0.0766 (15)	0.0436 (12)	0.0043 (11)	0.0163 (10)	−0.0034 (11)

Geometric parameters (Å, º)

S1—C1	1.7788 (16)	N1—C13	1.476 (2)
C1—C6	1.391 (3)	N1—H1A	0.91 (1)
C1—C2	1.395 (3)	N1—H1B	0.91 (1)
C2—C3	1.387 (3)	N1—H1C	0.90 (1)
C2—H2	0.95	C13—C14	1.496 (3)
C3—C4	1.383 (3)	C13—H13A	0.99
C3—H3	0.95	C13—H13B	0.99
C4—C5	1.372 (3)	C14—C15	1.532 (3)
C4—H4	0.95	C14—H14	1
C5—C6	1.389 (3)	C15—H15A	0.98
C5—H5	0.95	C15—H15B	0.98
C6—H6	0.95	C15—H15C	0.98
S2—C7	1.7738 (19)	O2—C17	1.421 (2)
C7—C12	1.395 (3)	O2—H2O	0.84
C7—C8	1.400 (2)	N2—C16	1.487 (2)
C8—C9	1.385 (3)	N2—H2A	0.90 (1)
C8—H8	0.95	N2—H2B	0.90 (1)
C9—C10	1.369 (3)	N2—H2C	0.90 (1)
C9—H9	0.95	C16—C17	1.514 (2)
C10—C11	1.378 (3)	C16—H16A	0.99
C10—H10	0.95	C16—H16B	0.99
C11—C12	1.400 (3)	C17—C18	1.515 (2)
C11—H11	0.95	C17—H17	1.00
C12—H12	0.95	C18—H18A	0.98
O1—C14	1.434 (3)	C18—H18B	0.98
O1—H1O	0.84	C18—H18C	0.98
C6—C1—C2	117.89 (16)	N1—C13—C14	111.39 (16)
C6—C1—S1	120.59 (13)	N1—C13—H13A	109.3
C2—C1—S1	121.52 (14)	C14—C13—H13A	109.3
C3—C2—C1	120.55 (19)	N1—C13—H13B	109.3
C3—C2—H2	119.7	C14—C13—H13B	109.3
C1—C2—H2	119.7	H13A—C13—H13B	108
C4—C3—C2	120.81 (19)	O1—C14—C13	110.28 (15)
C4—C3—H3	119.6	O1—C14—C15	110.90 (18)
C2—C3—H3	119.6	C13—C14—C15	110.96 (19)
C5—C4—C3	119.09 (18)	O1—C14—H14	108.2
C5—C4—H4	120.5	C13—C14—H14	108.2
C3—C4—H4	120.5	C15—C14—H14	108.2
C4—C5—C6	120.6 (2)	C14—C15—H15A	109.5
C4—C5—H5	119.7	C14—C15—H15B	109.5
C6—C5—H5	119.7	H15A—C15—H15B	109.5
C5—C6—C1	121.08 (17)	C14—C15—H15C	109.5
C5—C6—H6	119.5	H15A—C15—H15C	109.5
C1—C6—H6	119.5	H15B—C15—H15C	109.5
C12—C7—C8	116.92 (17)	C17—O2—H2O	109.5
C12—C7—S2	122.19 (14)	C16—N2—H2A	113.3 (12)
C8—C7—S2	120.88 (13)	C16—N2—H2B	107.9 (14)
C9—C8—C7	121.80 (18)	H2A—N2—H2B	106.3 (19)
C9—C8—H8	119.1	C16—N2—H2C	110.4 (13)
C7—C8—H8	119.1	H2A—N2—H2C	110.3 (19)
C10—C9—C8	120.8 (2)	H2B—N2—H2C	108.4 (19)
C10—C9—H9	119.6	N2—C16—C17	110.95 (14)
C8—C9—H9	119.6	N2—C16—H16A	109.4
C9—C10—C11	118.7 (2)	C17—C16—H16A	109.4
C9—C10—H10	120.6	N2—C16—H16B	109.4
C11—C10—H10	120.6	C17—C16—H16B	109.4
C10—C11—C12	121.2 (2)	H16A—C16—H16B	108
C10—C11—H11	119.4	O2—C17—C16	107.16 (14)
C12—C11—H11	119.4	O2—C17—C18	111.03 (15)
C7—C12—C11	120.53 (19)	C16—C17—C18	110.45 (15)
C7—C12—H12	119.7	O2—C17—H17	109.4
C11—C12—H12	119.7	C16—C17—H17	109.4
C14—O1—H1O	109.5	C18—C17—H17	109.4
C13—N1—H1A	111.5 (13)	C17—C18—H18A	109.5
C13—N1—H1B	107.1 (15)	C17—C18—H18B	109.5
H1A—N1—H1B	112 (2)	H18A—C18—H18B	109.5
C13—N1—H1C	112.2 (13)	C17—C18—H18C	109.5
H1A—N1—H1C	105.0 (19)	H18A—C18—H18C	109.5
H1B—N1—H1C	109 (2)	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···S2^i	0.84	2.42	3.2379 (18)	166
N1—H1A···S1	0.91 (1)	2.34 (1)	3.2401 (18)	170 (2)
N1—H1B···S2^ii	0.91 (1)	2.31 (1)	3.2200 (19)	174 (2)
N1—H1C···S1^ii	0.90 (1)	2.46 (1)	3.2920 (18)	154 (2)
O2—H2O···S2	0.84	2.31	3.1530 (14)	178
N2—H2A···S2^iii	0.90 (1)	2.62 (1)	3.397 (2)	145 (2)
N2—H2B···S1^ii	0.90 (1)	2.35 (1)	3.2218 (17)	163 (2)
N2—H2C···S1^iv	0.90 (1)	2.47 (1)	3.2730 (17)	148 (2)
N2—H2C···O1^v	0.90 (1)	2.57 (2)	3.187 (2)	126 (2)

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