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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013069/hb7855sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013069/hb7855Isup2.hkl
Contains datablock I

docx

Microsoft Word (DOCX) file https://doi.org/10.1107/S2056989019013069/hb7855sup3.docx
Hirshfeld surface analysis figures

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013069/hb7855Isup4.cml
Supplementary material

CCDC reference: 1955268

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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+·BrF(000) = 552
Mr = 274.19Dx = 1.626 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.5986 (5) ÅCell parameters from 3357 reflections
b = 8.7168 (3) Åθ = 2.9–26.3°
c = 13.0308 (5) ŵ = 3.82 mm1
β = 111.513 (2)°T = 150 K
V = 1119.99 (8) Å3Block, colorless
Z = 40.18 × 0.14 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
1998 reflections with I > 2σ(I)
φ and ω scansRint = 0.029
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
θmax = 26.4°, θmin = 2.9°
Tmin = 0.534, Tmax = 0.661h = 1313
8461 measured reflectionsk = 1010
2303 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: mixed
wR(F2) = 0.070H-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 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
Br10.14662 (3)0.38142 (3)0.26547 (2)0.02369 (10)
S10.31116 (7)0.46985 (7)0.58677 (5)0.02034 (15)
N10.4802 (2)0.6893 (2)0.61070 (15)0.0159 (4)
N20.5487 (2)0.8083 (2)0.57955 (15)0.0183 (4)
H2A0.6355510.7766930.6073500.022*
H2B0.5359010.8917530.6152300.022*
N30.3577 (2)0.6293 (2)0.42850 (16)0.0179 (4)
H3A0.2927190.5721570.3792250.021*
H3B0.3905090.7093170.4024150.021*
C10.4372 (3)0.5007 (3)0.72776 (19)0.0214 (5)
H1A0.5139950.4270320.7413770.026*
C20.4890 (3)0.6645 (3)0.72463 (19)0.0189 (5)
H2C0.4320080.7397980.7447490.023*
H2D0.5838320.6750800.7767590.023*
C30.3879 (2)0.6085 (3)0.53385 (19)0.0154 (5)
C40.3746 (2)0.4760 (3)0.81375 (18)0.0168 (5)
C50.4280 (3)0.3584 (3)0.8912 (2)0.0212 (5)
H5A0.4975850.2934620.8863580.025*
C60.3773 (3)0.3379 (3)0.97571 (19)0.0208 (5)
H6A0.4121910.2585531.0285820.025*
C70.2769 (3)0.4330 (3)0.9816 (2)0.0225 (5)
H7A0.2442080.4205211.0399050.027*
C80.2230 (3)0.5463 (3)0.9041 (2)0.0265 (6)
H8A0.1526100.6104770.9084070.032*
C90.2715 (3)0.5662 (3)0.8203 (2)0.0249 (6)
H9A0.2332080.6434240.7663880.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02460 (15)0.02084 (15)0.02181 (15)0.00181 (11)0.00401 (11)0.00181 (10)
S10.0263 (3)0.0175 (3)0.0173 (3)0.0062 (3)0.0081 (2)0.0012 (2)
N10.0197 (10)0.0165 (10)0.0132 (9)0.0036 (8)0.0078 (8)0.0004 (8)
N20.0208 (11)0.0162 (10)0.0198 (10)0.0030 (9)0.0099 (9)0.0004 (8)
N30.0239 (11)0.0151 (10)0.0144 (10)0.0011 (9)0.0066 (8)0.0014 (8)
C10.0215 (13)0.0233 (13)0.0184 (12)0.0033 (11)0.0061 (10)0.0023 (10)
C20.0225 (13)0.0215 (12)0.0126 (11)0.0041 (10)0.0064 (10)0.0018 (10)
C30.0176 (12)0.0121 (11)0.0178 (12)0.0027 (9)0.0082 (10)0.0009 (9)
C40.0171 (12)0.0193 (12)0.0131 (11)0.0054 (10)0.0046 (9)0.0010 (9)
C50.0175 (12)0.0183 (12)0.0255 (13)0.0020 (10)0.0051 (10)0.0066 (10)
C60.0244 (13)0.0193 (12)0.0147 (12)0.0050 (10)0.0027 (10)0.0016 (10)
C70.0215 (13)0.0253 (13)0.0214 (13)0.0100 (11)0.0085 (11)0.0029 (11)
C80.0208 (13)0.0258 (14)0.0335 (15)0.0012 (11)0.0108 (12)0.0007 (12)
C90.0219 (13)0.0246 (13)0.0266 (14)0.0041 (11)0.0070 (11)0.0036 (11)
Geometric parameters (Å, º) top
S1—C31.735 (2)C2—H2C0.9900
S1—C11.853 (2)C2—H2D0.9900
N1—C31.318 (3)C4—C91.374 (4)
N1—N21.408 (3)C4—C51.404 (3)
N1—C21.469 (3)C5—C61.403 (4)
N2—H2A0.9000C5—H5A0.9500
N2—H2B0.9000C6—C71.373 (4)
N3—C31.303 (3)C6—H6A0.9500
N3—H3A0.9000C7—C81.378 (4)
N3—H3B0.9000C7—H7A0.9500
C1—C41.513 (3)C8—C91.378 (4)
C1—C21.535 (4)C8—H8A0.9500
C1—H1A1.0000C9—H9A0.9500
C3—S1—C191.16 (11)N3—C3—N1123.6 (2)
C3—N1—N2119.48 (18)N3—C3—S1123.08 (18)
C3—N1—C2116.3 (2)N1—C3—S1113.33 (17)
N2—N1—C2123.48 (18)C9—C4—C5119.6 (2)
N1—N2—H2A102.6C9—C4—C1122.7 (2)
N1—N2—H2B104.8C5—C4—C1117.7 (2)
H2A—N2—H2B111.4C6—C5—C4119.2 (2)
C3—N3—H3A120.2C6—C5—H5A120.4
C3—N3—H3B121.7C4—C5—H5A120.4
H3A—N3—H3B117.4C7—C6—C5119.6 (2)
C4—C1—C2114.2 (2)C7—C6—H6A120.2
C4—C1—S1111.16 (17)C5—C6—H6A120.2
C2—C1—S1104.09 (16)C6—C7—C8120.9 (2)
C4—C1—H1A109.1C6—C7—H7A119.5
C2—C1—H1A109.1C8—C7—H7A119.5
S1—C1—H1A109.1C9—C8—C7119.7 (3)
N1—C2—C1105.85 (19)C9—C8—H8A120.1
N1—C2—H2C110.6C7—C8—H8A120.1
C1—C2—H2C110.6C4—C9—C8120.9 (2)
N1—C2—H2D110.6C4—C9—H9A119.5
C1—C2—H2D110.6C8—C9—H9A119.5
H2C—C2—H2D108.7
C3—S1—C1—C4147.17 (19)C2—C1—C4—C953.9 (3)
C3—S1—C1—C223.78 (17)S1—C1—C4—C963.5 (3)
C3—N1—C2—C126.7 (3)C2—C1—C4—C5124.2 (2)
N2—N1—C2—C1163.3 (2)S1—C1—C4—C5118.4 (2)
C4—C1—C2—N1152.1 (2)C9—C4—C5—C61.7 (4)
S1—C1—C2—N130.7 (2)C1—C4—C5—C6176.5 (2)
N2—N1—C3—N31.9 (3)C4—C5—C6—C70.2 (4)
C2—N1—C3—N3172.3 (2)C5—C6—C7—C81.5 (4)
N2—N1—C3—S1178.62 (16)C6—C7—C8—C90.9 (4)
C2—N1—C3—S18.2 (3)C5—C4—C9—C82.2 (4)
C1—S1—C3—N3169.2 (2)C1—C4—C9—C8175.8 (2)
C1—S1—C3—N110.29 (19)C7—C8—C9—C41.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.902.683.530 (2)158
N2—H2B···Br1ii0.902.733.524 (2)148
N3—H3A···Br10.902.383.271 (2)169
N3—H3B···Br1iii0.902.563.337 (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 top
ContactPercentage contribution
H···H41.5
Br···N/N···Br24.1
C···H/H···C13.8
S···H/H···S11.7
N···H/H···N3.6
C···C3.3
N···C/C···N1.5
N···N0.3
S···C/C···S0.3
 

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