Crystal structure and Hirshfeld surface analysis of 2-amino-5-{(1E)-1-[(carbamo­thioyl­amino)­imino]eth­yl}-4-methyl-1,3-thia­zol-3-ium chloride monohydrate

In the crystal, the 2-amino-5-{(1E)-1-[(carbamo­thioyl­amino)­imino]­eth­yl}-4-methyl-1,3-thia­zol-3-ium cations are linked by O—H...Cl, N—H...Cl, N—H...O, N—H...S and C—H...S hydrogen bonds, forming a tri-periodic network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.115
• Data-to-parameter ratio = 35.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT354_ALERT_3_C Short  O-H (X0.82,N0.98A)  Ow1      - Hw2      .       0.71 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H6C      ..H41      .       1.97 Ang.
                                                      x,y,z  =      1_555 Check
PLAT417_ALERT_2_C Short Inter D-H..H-D       Hw2      ..H12      .       2.14 Ang.
                                                1-x,1-y,1-z  =      2_666 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.996 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          7 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2-Amino-5-{(1E)-1-[(carbamothioylamino)imino]ethyl}-4-methyl-1,3-thiazol-3-ium chloride monohydrate

Crystal data

C7H12N5S2^+·Cl^−·H2O	Z = 2
Mr = 283.80	F(000) = 296
Triclinic, P1	Dx = 1.500 Mg m^−3
a = 6.3279 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7816 (6) Å	Cell parameters from 9921 reflections
c = 14.1342 (10) Å	θ = 3.0–36.3°
α = 77.191 (3)°	µ = 0.62 mm^−1
β = 83.660 (3)°	T = 293 K
γ = 67.860 (2)°	Prism, colourless
V = 628.35 (8) Å^3	0.04 × 0.03 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer	4589 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.053
Absorption correction: multi-scan (SADABS; Krause et al., 2015).	θmax = 36.3°, θmin = 3.0°
Tmin = 0.570, Tmax = 0.747	h = −10→10
34019 measured reflections	k = −12→12
6058 independent reflections	l = −23→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.0995P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
6058 reflections	Δρmax = 0.50 e Å^−3
171 parameters	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.00052 (18)	0.66580 (16)	0.37114 (8)	0.0336 (2)
C2	1.00425 (17)	0.58328 (15)	0.22387 (8)	0.03023 (18)
C3	0.78120 (16)	0.69558 (14)	0.23070 (7)	0.02811 (17)
C4	1.1391 (2)	0.4821 (2)	0.14588 (10)	0.0429 (3)
H4A	1.053893	0.420248	0.123677	0.064*
H4B	1.281001	0.389685	0.171192	0.064*
H4C	1.169126	0.571545	0.092670	0.064*
C5	0.59592 (16)	0.76248 (15)	0.16319 (7)	0.02893 (17)
C6	0.6438 (2)	0.7189 (2)	0.06335 (10)	0.0474 (3)
H6A	0.648883	0.593175	0.065682	0.071*
H6B	0.788013	0.727617	0.039126	0.071*
H6C	0.525339	0.807944	0.021177	0.071*
C7	0.01732 (16)	1.05991 (15)	0.17123 (7)	0.02918 (17)
N1	1.0867 (2)	0.6736 (2)	0.45014 (10)	0.0471 (3)
H11	1.215 (4)	0.611 (3)	0.4604 (14)	0.057*
H12	0.992 (4)	0.756 (3)	0.4827 (15)	0.057*
N2	1.12182 (15)	0.56820 (14)	0.30449 (7)	0.03419 (18)
H2	1.261 (3)	0.496 (2)	0.3136 (12)	0.041*
N3	0.40159 (14)	0.86322 (14)	0.19705 (7)	0.03073 (16)
N4	0.21575 (15)	0.94127 (14)	0.13782 (7)	0.03273 (18)
H41	0.214 (3)	0.927 (2)	0.0734 (12)	0.039*
N5	0.01285 (18)	1.09259 (17)	0.25930 (8)	0.0395 (2)
H51	−0.101 (3)	1.160 (3)	0.2836 (13)	0.047*
H52	0.117 (3)	1.046 (3)	0.2953 (13)	0.047*
S1	0.71982 (4)	0.78020 (4)	0.33975 (2)	0.03514 (7)
S2	−0.21036 (5)	1.16255 (5)	0.09918 (2)	0.03939 (8)
Cl1	0.57747 (5)	0.30475 (5)	0.39936 (2)	0.04264 (8)
OW1	0.23501 (19)	0.07771 (18)	0.43851 (9)	0.0517 (3)
HW1	0.288 (4)	−0.009 (4)	0.4806 (19)	0.078*
HW2	0.308 (4)	0.131 (4)	0.4302 (19)	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0290 (4)	0.0352 (5)	0.0351 (5)	−0.0092 (4)	−0.0118 (4)	−0.0030 (4)
C2	0.0241 (4)	0.0307 (4)	0.0325 (4)	−0.0064 (3)	−0.0040 (3)	−0.0042 (3)
C3	0.0230 (4)	0.0313 (4)	0.0283 (4)	−0.0065 (3)	−0.0052 (3)	−0.0062 (3)
C4	0.0341 (5)	0.0456 (6)	0.0429 (6)	−0.0052 (5)	0.0031 (4)	−0.0152 (5)
C5	0.0240 (4)	0.0324 (4)	0.0296 (4)	−0.0081 (3)	−0.0065 (3)	−0.0057 (3)
C6	0.0341 (5)	0.0638 (8)	0.0390 (6)	−0.0028 (5)	−0.0082 (4)	−0.0231 (6)
C7	0.0230 (4)	0.0327 (4)	0.0301 (4)	−0.0080 (3)	−0.0063 (3)	−0.0037 (3)
N1	0.0405 (5)	0.0552 (7)	0.0440 (6)	−0.0094 (5)	−0.0204 (4)	−0.0116 (5)
N2	0.0236 (3)	0.0361 (4)	0.0378 (4)	−0.0047 (3)	−0.0092 (3)	−0.0043 (3)
N3	0.0225 (3)	0.0370 (4)	0.0303 (4)	−0.0071 (3)	−0.0071 (3)	−0.0054 (3)
N4	0.0236 (3)	0.0403 (5)	0.0309 (4)	−0.0050 (3)	−0.0076 (3)	−0.0086 (3)
N5	0.0290 (4)	0.0525 (6)	0.0316 (4)	−0.0055 (4)	−0.0053 (3)	−0.0121 (4)
S1	0.02593 (11)	0.04268 (15)	0.03359 (13)	−0.00389 (10)	−0.00727 (9)	−0.01324 (11)
S2	0.02756 (12)	0.04546 (16)	0.03856 (14)	−0.00214 (10)	−0.01341 (10)	−0.00894 (12)
Cl1	0.02891 (12)	0.04757 (16)	0.04456 (16)	−0.00184 (10)	−0.01143 (10)	−0.01183 (12)
OW1	0.0426 (5)	0.0549 (6)	0.0542 (6)	−0.0121 (4)	−0.0169 (4)	−0.0060 (5)

Geometric parameters (Å, º)

C1—N1	1.3181 (16)	C6—H6B	0.9600
C1—N2	1.3309 (16)	C6—H6C	0.9600
C1—S1	1.7180 (11)	C7—N5	1.3198 (15)
C2—C3	1.3575 (13)	C7—N4	1.3567 (14)
C2—N2	1.3885 (14)	C7—S2	1.6872 (10)
C2—C4	1.4945 (16)	N1—H11	0.79 (2)
C3—C5	1.4570 (14)	N1—H12	0.87 (2)
C3—S1	1.7565 (10)	N2—H2	0.854 (18)
C4—H4A	0.9600	N3—N4	1.3806 (12)
C4—H4B	0.9600	N4—H41	0.943 (17)
C4—H4C	0.9600	N5—H51	0.81 (2)
C5—N3	1.2906 (13)	N5—H52	0.80 (2)
C5—C6	1.4961 (16)	OW1—HW1	0.78 (3)
C6—H6A	0.9600	OW1—HW2	0.71 (3)
N1—C1—N2	124.00 (11)	C5—C6—H6C	109.5
N1—C1—S1	124.99 (10)	H6A—C6—H6C	109.5
N2—C1—S1	111.01 (8)	H6B—C6—H6C	109.5
C3—C2—N2	111.36 (9)	N5—C7—N4	117.81 (9)
C3—C2—C4	131.66 (10)	N5—C7—S2	122.67 (8)
N2—C2—C4	116.95 (9)	N4—C7—S2	119.51 (8)
C2—C3—C5	131.75 (10)	C1—N1—H11	118.0 (15)
C2—C3—S1	111.21 (8)	C1—N1—H12	113.9 (14)
C5—C3—S1	116.95 (7)	H11—N1—H12	127.9 (19)
C2—C4—H4A	109.5	C1—N2—C2	115.94 (9)
C2—C4—H4B	109.5	C1—N2—H2	120.9 (11)
H4A—C4—H4B	109.5	C2—N2—H2	123.1 (11)
C2—C4—H4C	109.5	C5—N3—N4	118.97 (9)
H4A—C4—H4C	109.5	C7—N4—N3	118.45 (9)
H4B—C4—H4C	109.5	C7—N4—H41	115.1 (10)
N3—C5—C3	113.92 (9)	N3—N4—H41	126.3 (10)
N3—C5—C6	126.22 (10)	C7—N5—H51	122.4 (14)
C3—C5—C6	119.81 (9)	C7—N5—H52	125.2 (13)
C5—C6—H6A	109.5	H51—N5—H52	112.4 (18)
C5—C6—H6B	109.5	C1—S1—C3	90.43 (5)
H6A—C6—H6B	109.5	HW1—OW1—HW2	106 (3)
N2—C2—C3—C5	175.76 (11)	C4—C2—N2—C1	177.27 (11)
C4—C2—C3—C5	−2.4 (2)	C3—C5—N3—N4	177.15 (9)
N2—C2—C3—S1	−0.57 (12)	C6—C5—N3—N4	−0.16 (18)
C4—C2—C3—S1	−178.69 (11)	N5—C7—N4—N3	−0.63 (16)
C2—C3—C5—N3	177.59 (11)	S2—C7—N4—N3	178.17 (8)
S1—C3—C5—N3	−6.25 (13)	C5—N3—N4—C7	−174.48 (10)
C2—C3—C5—C6	−4.92 (19)	N1—C1—S1—C3	177.38 (12)
S1—C3—C5—C6	171.25 (10)	N2—C1—S1—C3	−2.17 (9)
N1—C1—N2—C2	−177.21 (12)	C2—C3—S1—C1	1.55 (9)
S1—C1—N2—C2	2.34 (13)	C5—C3—S1—C1	−175.38 (9)
C3—C2—N2—C1	−1.15 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—HW1···Cl1^i	0.79 (3)	2.45 (3)	3.2298 (13)	171 (3)
N2—H2···Cl1^ii	0.853 (18)	2.277 (18)	3.0812 (11)	157.2 (15)
OW1—HW2···Cl1	0.71 (3)	2.50 (3)	3.2111 (14)	178 (3)
N1—H11···Cl1^iii	0.78 (3)	2.81 (2)	3.2398 (15)	117.0 (18)
N1—H12···OW1^iv	0.87 (2)	1.97 (2)	2.8354 (19)	174 (2)
N4—H41···S2^v	0.943 (16)	2.686 (16)	3.6223 (11)	172.0 (14)
N5—H51···Cl1^vi	0.81 (2)	2.54 (2)	3.3243 (13)	164.9 (18)
N5—H52···OW1^vii	0.80 (2)	2.326 (19)	2.9899 (17)	141.2 (19)
N5—H52···N3	0.80 (2)	2.36 (2)	2.6306 (16)	100.6 (15)
C6—H6C···N4	0.96	2.48	2.8433 (18)	102
C6—H6C···S2^v	0.96	2.67	3.4923 (15)	143

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