In the crystal of the title salt, the cations and anions are linked
via N—H

Br hydrogen bonds to form a three-dimensional network.
Supporting information
CCDC reference: 1955268
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.027
- wR factor = 0.070
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 --C5 . 5.1 s.u.
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 4 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT793_ALERT_4_G Model has Chirality at C1 (Centro SPGR) R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 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. 4 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2003).
3-Amino-5-phenylthiazolidin-2-iminium bromide
top
Crystal data top
C9H12N3S+·Br− | F(000) = 552 |
Mr = 274.19 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5986 (5) Å | Cell parameters from 3357 reflections |
b = 8.7168 (3) Å | θ = 2.9–26.3° |
c = 13.0308 (5) Å | µ = 3.82 mm−1 |
β = 111.513 (2)° | T = 150 K |
V = 1119.99 (8) Å3 | Block, colorless |
Z = 4 | 0.18 × 0.14 × 0.11 mm |
Data collection top
Bruker APEXII CCD diffractometer | 1998 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | θmax = 26.4°, θmin = 2.9° |
Tmin = 0.534, Tmax = 0.661 | h = −13→13 |
8461 measured reflections | k = −10→10 |
2303 independent reflections | l = −16→16 |
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)] = 0.027 | Hydrogen site location: mixed |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.5896P] where P = (Fo2 + 2Fc2)/3 |
2303 reflections | (Δ/σ)max = 0.001 |
127 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.33 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 | Uiso*/Ueq | |
Br1 | 0.14662 (3) | 0.38142 (3) | 0.26547 (2) | 0.02369 (10) | |
S1 | 0.31116 (7) | 0.46985 (7) | 0.58677 (5) | 0.02034 (15) | |
N1 | 0.4802 (2) | 0.6893 (2) | 0.61070 (15) | 0.0159 (4) | |
N2 | 0.5487 (2) | 0.8083 (2) | 0.57955 (15) | 0.0183 (4) | |
H2A | 0.635551 | 0.776693 | 0.607350 | 0.022* | |
H2B | 0.535901 | 0.891753 | 0.615230 | 0.022* | |
N3 | 0.3577 (2) | 0.6293 (2) | 0.42850 (16) | 0.0179 (4) | |
H3A | 0.292719 | 0.572157 | 0.379225 | 0.021* | |
H3B | 0.390509 | 0.709317 | 0.402415 | 0.021* | |
C1 | 0.4372 (3) | 0.5007 (3) | 0.72776 (19) | 0.0214 (5) | |
H1A | 0.513995 | 0.427032 | 0.741377 | 0.026* | |
C2 | 0.4890 (3) | 0.6645 (3) | 0.72463 (19) | 0.0189 (5) | |
H2C | 0.432008 | 0.739798 | 0.744749 | 0.023* | |
H2D | 0.583832 | 0.675080 | 0.776759 | 0.023* | |
C3 | 0.3879 (2) | 0.6085 (3) | 0.53385 (19) | 0.0154 (5) | |
C4 | 0.3746 (2) | 0.4760 (3) | 0.81375 (18) | 0.0168 (5) | |
C5 | 0.4280 (3) | 0.3584 (3) | 0.8912 (2) | 0.0212 (5) | |
H5A | 0.497585 | 0.293462 | 0.886358 | 0.025* | |
C6 | 0.3773 (3) | 0.3379 (3) | 0.97571 (19) | 0.0208 (5) | |
H6A | 0.412191 | 0.258553 | 1.028582 | 0.025* | |
C7 | 0.2769 (3) | 0.4330 (3) | 0.9816 (2) | 0.0225 (5) | |
H7A | 0.244208 | 0.420521 | 1.039905 | 0.027* | |
C8 | 0.2230 (3) | 0.5463 (3) | 0.9041 (2) | 0.0265 (6) | |
H8A | 0.152610 | 0.610477 | 0.908407 | 0.032* | |
C9 | 0.2715 (3) | 0.5662 (3) | 0.8203 (2) | 0.0249 (6) | |
H9A | 0.233208 | 0.643424 | 0.766388 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02460 (15) | 0.02084 (15) | 0.02181 (15) | −0.00181 (11) | 0.00401 (11) | −0.00181 (10) |
S1 | 0.0263 (3) | 0.0175 (3) | 0.0173 (3) | −0.0062 (3) | 0.0081 (2) | −0.0012 (2) |
N1 | 0.0197 (10) | 0.0165 (10) | 0.0132 (9) | −0.0036 (8) | 0.0078 (8) | −0.0004 (8) |
N2 | 0.0208 (11) | 0.0162 (10) | 0.0198 (10) | −0.0030 (9) | 0.0099 (9) | −0.0004 (8) |
N3 | 0.0239 (11) | 0.0151 (10) | 0.0144 (10) | −0.0011 (9) | 0.0066 (8) | −0.0014 (8) |
C1 | 0.0215 (13) | 0.0233 (13) | 0.0184 (12) | 0.0033 (11) | 0.0061 (10) | 0.0023 (10) |
C2 | 0.0225 (13) | 0.0215 (12) | 0.0126 (11) | −0.0041 (10) | 0.0064 (10) | −0.0018 (10) |
C3 | 0.0176 (12) | 0.0121 (11) | 0.0178 (12) | 0.0027 (9) | 0.0082 (10) | −0.0009 (9) |
C4 | 0.0171 (12) | 0.0193 (12) | 0.0131 (11) | −0.0054 (10) | 0.0046 (9) | −0.0010 (9) |
C5 | 0.0175 (12) | 0.0183 (12) | 0.0255 (13) | −0.0020 (10) | 0.0051 (10) | −0.0066 (10) |
C6 | 0.0244 (13) | 0.0193 (12) | 0.0147 (12) | −0.0050 (10) | 0.0027 (10) | 0.0016 (10) |
C7 | 0.0215 (13) | 0.0253 (13) | 0.0214 (13) | −0.0100 (11) | 0.0085 (11) | −0.0029 (11) |
C8 | 0.0208 (13) | 0.0258 (14) | 0.0335 (15) | −0.0012 (11) | 0.0108 (12) | −0.0007 (12) |
C9 | 0.0219 (13) | 0.0246 (13) | 0.0266 (14) | 0.0041 (11) | 0.0070 (11) | 0.0036 (11) |
Geometric parameters (Å, º) top
S1—C3 | 1.735 (2) | C2—H2C | 0.9900 |
S1—C1 | 1.853 (2) | C2—H2D | 0.9900 |
N1—C3 | 1.318 (3) | C4—C9 | 1.374 (4) |
N1—N2 | 1.408 (3) | C4—C5 | 1.404 (3) |
N1—C2 | 1.469 (3) | C5—C6 | 1.403 (4) |
N2—H2A | 0.9000 | C5—H5A | 0.9500 |
N2—H2B | 0.9000 | C6—C7 | 1.373 (4) |
N3—C3 | 1.303 (3) | C6—H6A | 0.9500 |
N3—H3A | 0.9000 | C7—C8 | 1.378 (4) |
N3—H3B | 0.9000 | C7—H7A | 0.9500 |
C1—C4 | 1.513 (3) | C8—C9 | 1.378 (4) |
C1—C2 | 1.535 (4) | C8—H8A | 0.9500 |
C1—H1A | 1.0000 | C9—H9A | 0.9500 |
| | | |
C3—S1—C1 | 91.16 (11) | N3—C3—N1 | 123.6 (2) |
C3—N1—N2 | 119.48 (18) | N3—C3—S1 | 123.08 (18) |
C3—N1—C2 | 116.3 (2) | N1—C3—S1 | 113.33 (17) |
N2—N1—C2 | 123.48 (18) | C9—C4—C5 | 119.6 (2) |
N1—N2—H2A | 102.6 | C9—C4—C1 | 122.7 (2) |
N1—N2—H2B | 104.8 | C5—C4—C1 | 117.7 (2) |
H2A—N2—H2B | 111.4 | C6—C5—C4 | 119.2 (2) |
C3—N3—H3A | 120.2 | C6—C5—H5A | 120.4 |
C3—N3—H3B | 121.7 | C4—C5—H5A | 120.4 |
H3A—N3—H3B | 117.4 | C7—C6—C5 | 119.6 (2) |
C4—C1—C2 | 114.2 (2) | C7—C6—H6A | 120.2 |
C4—C1—S1 | 111.16 (17) | C5—C6—H6A | 120.2 |
C2—C1—S1 | 104.09 (16) | C6—C7—C8 | 120.9 (2) |
C4—C1—H1A | 109.1 | C6—C7—H7A | 119.5 |
C2—C1—H1A | 109.1 | C8—C7—H7A | 119.5 |
S1—C1—H1A | 109.1 | C9—C8—C7 | 119.7 (3) |
N1—C2—C1 | 105.85 (19) | C9—C8—H8A | 120.1 |
N1—C2—H2C | 110.6 | C7—C8—H8A | 120.1 |
C1—C2—H2C | 110.6 | C4—C9—C8 | 120.9 (2) |
N1—C2—H2D | 110.6 | C4—C9—H9A | 119.5 |
C1—C2—H2D | 110.6 | C8—C9—H9A | 119.5 |
H2C—C2—H2D | 108.7 | | |
| | | |
C3—S1—C1—C4 | 147.17 (19) | C2—C1—C4—C9 | 53.9 (3) |
C3—S1—C1—C2 | 23.78 (17) | S1—C1—C4—C9 | −63.5 (3) |
C3—N1—C2—C1 | 26.7 (3) | C2—C1—C4—C5 | −124.2 (2) |
N2—N1—C2—C1 | −163.3 (2) | S1—C1—C4—C5 | 118.4 (2) |
C4—C1—C2—N1 | −152.1 (2) | C9—C4—C5—C6 | −1.7 (4) |
S1—C1—C2—N1 | −30.7 (2) | C1—C4—C5—C6 | 176.5 (2) |
N2—N1—C3—N3 | 1.9 (3) | C4—C5—C6—C7 | −0.2 (4) |
C2—N1—C3—N3 | 172.3 (2) | C5—C6—C7—C8 | 1.5 (4) |
N2—N1—C3—S1 | −178.62 (16) | C6—C7—C8—C9 | −0.9 (4) |
C2—N1—C3—S1 | −8.2 (3) | C5—C4—C9—C8 | 2.2 (4) |
C1—S1—C3—N3 | 169.2 (2) | C1—C4—C9—C8 | −175.8 (2) |
C1—S1—C3—N1 | −10.29 (19) | C7—C8—C9—C4 | −1.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Br1i | 0.90 | 2.68 | 3.530 (2) | 158 |
N2—H2B···Br1ii | 0.90 | 2.73 | 3.524 (2) | 148 |
N3—H3A···Br1 | 0.90 | 2.38 | 3.271 (2) | 169 |
N3—H3B···Br1iii | 0.90 | 2.56 | 3.337 (2) | 145 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Percentage contributions of interatomic contacts to the
Hirshfeld surface for the title salt topContact | Percentage contribution |
H···H | 41.5 |
Br···N/N···Br | 24.1 |
C···H/H···C | 13.8 |
S···H/H···S | 11.7 |
N···H/H···N | 3.6 |
C···C | 3.3 |
N···C/C···N | 1.5 |
N···N | 0.3 |
S···C/C···S | 0.3 |