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The title thio­semicarbazide derivative, C10H16ClN5S·H2O, crystallized as a monohydrate. The mol­ecule has an E conformation about the azomethine C=N bond that links the methyl­hydrazine-1-carbo­thio­amide moiety to the imidazole ring. The butyl chain substituent on the imdazole ring is disordered over two sets of sites, with a refined occupancy ratio of 0.509 (9):0.491 (9). In the crystal, mol­ecules are linked by O—H...N and N—H...O hydrogen bonds involving the solvent water mol­ecule, forming chains along the c-axis direction. The chains are linked by O—H...S and N—H...S hydrogen bonds, forming a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616015145/su4057sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616015145/su4057Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616015145/su4057Isup3.cml
Supplementary material

CCDC reference: 1506723

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.150
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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Alert level C PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 6 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 5 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 18 Note PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 8 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note H2 O PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 90 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 39 Note
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 12 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 2 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: SAINT (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(E)-2-[(2-Butyl-4-chloro-1H-imidazol-5-yl)methylidene]-N-methylhydrazine-1-carbothioamide monohydrate top
Crystal data top
C10H16ClN5S·H2OF(000) = 616
Mr = 291.80Dx = 1.252 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.494 (4) ÅCell parameters from 5524 reflections
b = 17.665 (10) Åθ = 2.3–24.9°
c = 13.508 (8) ŵ = 0.38 mm1
β = 92.402 (9)°T = 300 K
V = 1548.2 (16) Å3Block, yellow
Z = 40.3 × 0.2 × 0.14 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
2347 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
phi and ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 88
Tmin = 0.895, Tmax = 0.949k = 2221
15205 measured reflectionsl = 1616
3151 independent reflections
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)] = 0.049Hydrogen site location: mixed
wR(F2) = 0.150H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0896P)2 + 0.1249P]
where P = (Fo2 + 2Fc2)/3
3151 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.23 e Å3
90 restraintsΔρmin = 0.31 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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Restrained distances C9A-C10A = C9-C10 = C9-C8 = C9A-C8A = C8-C7 = C8A-C7 1.54 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints C8 ~C8A ~C9 ~C9A ~C10 ~C10A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.02 4. Rigid body (RIGU) restrains C8, C8A, C9, C9A, C10, C10A with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Others Sof(H7BC)=Sof(H7BD)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)= Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1) Sof(H7AA)=Sof(H7AB)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)= Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1) 6.a Riding coordinates: O1(H1D,H1E) 6.b Secondary CH2 refined with riding coordinates: C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,H9B), C9A(H9AA,H9AB) 6.c Me refined with riding coordinates: C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F) 6.d Aromatic/amide H refined with riding coordinates: N1(H1), N4(H4), N5(H5), C3(H3) 6.e Idealised Me refined as rotating group: C1(H1A,H1B,H1C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl11.09917 (13)0.28647 (5)1.33664 (5)0.1203 (3)
S11.40870 (8)0.50705 (3)0.84042 (4)0.0775 (2)
N10.7716 (2)0.30301 (9)1.09668 (13)0.0680 (4)
H10.73900.31771.03740.082*
N20.7516 (3)0.24365 (10)1.23866 (15)0.0803 (5)
N31.0786 (2)0.39480 (9)1.02455 (12)0.0676 (4)
N41.2297 (2)0.43919 (9)0.98710 (13)0.0713 (4)
H41.33250.45411.02430.086*
N51.0461 (3)0.43806 (11)0.84178 (13)0.0777 (5)
H50.95460.41410.87370.093*
C11.0031 (4)0.45223 (17)0.73736 (19)0.1025 (8)
H1A0.97990.50540.72700.154*
H1B0.88240.42450.71550.154*
H1C1.11840.43620.70040.154*
C21.2143 (3)0.45908 (10)0.89093 (15)0.0650 (5)
C31.0989 (3)0.37222 (11)1.11367 (16)0.0689 (5)
H31.21170.38701.15380.083*
C40.9444 (3)0.32364 (11)1.15086 (14)0.0668 (5)
C50.9271 (3)0.28602 (12)1.23801 (17)0.0776 (6)
C60.6607 (3)0.25575 (11)1.15151 (18)0.0726 (5)
C70.4665 (4)0.21935 (15)1.1134 (2)0.0981 (8)
H7AA0.39300.20241.17040.118*0.491 (9)
H7AB0.38300.25851.08120.118*0.491 (9)
H7BC0.41130.24731.05650.118*0.509 (9)
H7BD0.36540.22061.16420.118*0.509 (9)
C80.4739 (19)0.1576 (8)1.0468 (9)0.138 (4)0.491 (9)
H8A0.41920.17690.98380.166*0.491 (9)
H8B0.37320.12161.06920.166*0.491 (9)
C8A0.5058 (15)0.1367 (5)1.0833 (7)0.101 (2)0.509 (9)
H8AA0.37720.10971.07070.122*0.509 (9)
H8AB0.58710.11021.13430.122*0.509 (9)
C90.6576 (17)0.1117 (7)1.0227 (7)0.141 (3)0.491 (9)
H9A0.66840.06471.05980.169*0.491 (9)
H9B0.78580.13981.02880.169*0.491 (9)
C9A0.6316 (17)0.1452 (5)0.9831 (7)0.130 (3)0.509 (9)
H9AA0.54310.16710.93100.157*0.509 (9)
H9AB0.74880.17850.99490.157*0.509 (9)
C100.5775 (17)0.1002 (7)0.9120 (6)0.157 (3)0.491 (9)
H10A0.67480.07020.87760.235*0.491 (9)
H10B0.44670.07470.91080.235*0.491 (9)
H10C0.56210.14860.88030.235*0.491 (9)
C10A0.708 (2)0.0645 (5)0.9501 (9)0.173 (4)0.509 (9)
H10D0.78300.06930.89060.259*0.509 (9)
H10E0.79660.04331.00160.259*0.509 (9)
H10F0.59150.03190.93790.259*0.509 (9)
O10.6591 (2)0.15312 (9)1.40012 (11)0.0909 (5)
H1D0.60780.11171.37850.136*
H1E0.67840.18081.34990.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1252 (6)0.1591 (8)0.0757 (5)0.0300 (5)0.0068 (4)0.0263 (4)
S10.0773 (4)0.0824 (4)0.0740 (4)0.0057 (2)0.0155 (3)0.0169 (3)
N10.0741 (9)0.0658 (9)0.0648 (10)0.0046 (7)0.0131 (8)0.0015 (8)
N20.0886 (11)0.0791 (11)0.0750 (13)0.0082 (9)0.0248 (10)0.0076 (9)
N30.0701 (9)0.0660 (9)0.0678 (11)0.0028 (7)0.0160 (7)0.0061 (8)
N40.0708 (9)0.0766 (10)0.0671 (11)0.0081 (8)0.0091 (8)0.0110 (8)
N50.0788 (11)0.0886 (12)0.0664 (11)0.0083 (9)0.0103 (9)0.0075 (9)
C10.1038 (17)0.132 (2)0.0707 (16)0.0195 (16)0.0034 (13)0.0140 (15)
C20.0692 (11)0.0610 (11)0.0656 (12)0.0053 (8)0.0138 (9)0.0047 (9)
C30.0759 (11)0.0653 (11)0.0661 (13)0.0026 (9)0.0101 (9)0.0034 (9)
C40.0760 (11)0.0633 (11)0.0619 (12)0.0017 (9)0.0146 (9)0.0001 (9)
C50.0891 (14)0.0808 (13)0.0636 (13)0.0051 (11)0.0133 (10)0.0068 (10)
C60.0743 (11)0.0682 (12)0.0771 (15)0.0021 (9)0.0231 (10)0.0008 (10)
C70.0727 (13)0.0956 (17)0.127 (2)0.0029 (12)0.0189 (13)0.0024 (16)
C80.123 (6)0.180 (8)0.110 (7)0.019 (5)0.016 (5)0.040 (6)
C8A0.086 (4)0.115 (5)0.101 (5)0.017 (3)0.013 (4)0.027 (4)
C90.173 (5)0.138 (7)0.111 (6)0.018 (5)0.001 (5)0.024 (5)
C9A0.165 (6)0.119 (5)0.109 (6)0.019 (4)0.027 (5)0.041 (4)
C100.182 (7)0.172 (7)0.115 (5)0.007 (6)0.003 (5)0.018 (5)
C10A0.227 (8)0.136 (6)0.159 (7)0.014 (5)0.057 (6)0.057 (5)
O10.1094 (11)0.0934 (10)0.0699 (10)0.0319 (9)0.0023 (8)0.0073 (8)
Geometric parameters (Å, º) top
Cl1—C51.703 (3)C7—H7BD0.9700
S1—C21.688 (2)C7—C81.415 (11)
N1—H10.8600C7—C8A1.540 (9)
N1—C41.363 (3)C8—H8A0.9700
N1—C61.345 (3)C8—H8B0.9700
N2—C51.364 (3)C8—C91.490 (13)
N2—C61.312 (3)C8A—H8AA0.9700
N3—N41.370 (2)C8A—H8AB0.9700
N3—C31.270 (3)C8A—C9A1.617 (12)
N4—H40.8600C9—H9A0.9700
N4—C21.345 (3)C9—H9B0.9700
N5—H50.8600C9—C101.575 (12)
N5—C11.448 (3)C9A—H9AA0.9700
N5—C21.308 (3)C9A—H9AB0.9700
C1—H1A0.9600C9A—C10A1.580 (12)
C1—H1B0.9600C10—H10A0.9600
C1—H1C0.9600C10—H10B0.9600
C3—H30.9300C10—H10C0.9600
C3—C41.428 (3)C10A—H10D0.9600
C4—C51.361 (3)C10A—H10E0.9600
C6—C71.488 (3)C10A—H10F0.9600
C7—H7AA0.9700O1—H1D0.8500
C7—H7AB0.9700O1—H1E0.8500
C7—H7BC0.9700
C4—N1—H1125.7C8—C7—H7AB107.3
C6—N1—H1125.7C8A—C7—H7BC109.5
C6—N1—C4108.54 (19)C8A—C7—H7BD109.5
C6—N2—C5104.44 (17)C7—C8—H8A105.5
C3—N3—N4118.86 (17)C7—C8—H8B105.5
N3—N4—H4120.6C7—C8—C9127.4 (10)
C2—N4—N3118.74 (17)H8A—C8—H8B106.0
C2—N4—H4120.6C9—C8—H8A105.5
C1—N5—H5117.7C9—C8—H8B105.5
C2—N5—H5117.7C7—C8A—H8AA111.1
C2—N5—C1124.62 (18)C7—C8A—H8AB111.1
N5—C1—H1A109.5C7—C8A—C9A103.1 (7)
N5—C1—H1B109.5H8AA—C8A—H8AB109.1
N5—C1—H1C109.5C9A—C8A—H8AA111.1
H1A—C1—H1B109.5C9A—C8A—H8AB111.1
H1A—C1—H1C109.5C8—C9—H9A113.2
H1B—C1—H1C109.5C8—C9—H9B113.2
N4—C2—S1119.65 (16)C8—C9—C1092.4 (10)
N5—C2—S1124.06 (17)H9A—C9—H9B110.6
N5—C2—N4116.27 (17)C10—C9—H9A113.2
N3—C3—H3120.8C10—C9—H9B113.2
N3—C3—C4118.4 (2)C8A—C9A—H9AA109.8
C4—C3—H3120.8C8A—C9A—H9AB109.8
N1—C4—C3123.13 (19)H9AA—C9A—H9AB108.3
C5—C4—N1103.76 (18)C10A—C9A—C8A109.2 (9)
C5—C4—C3133.1 (2)C10A—C9A—H9AA109.8
N2—C5—Cl1121.25 (17)C10A—C9A—H9AB109.8
C4—C5—Cl1126.82 (18)C9—C10—H10A109.5
C4—C5—N2111.9 (2)C9—C10—H10B109.5
N1—C6—C7122.9 (2)C9—C10—H10C109.5
N2—C6—N1111.4 (2)H10A—C10—H10B109.5
N2—C6—C7125.6 (2)H10A—C10—H10C109.5
C6—C7—H7AA107.3H10B—C10—H10C109.5
C6—C7—H7AB107.3C9A—C10A—H10D109.5
C6—C7—H7BC109.5C9A—C10A—H10E109.5
C6—C7—H7BD109.5C9A—C10A—H10F109.5
C6—C7—C8A110.7 (4)H10D—C10A—H10E109.5
H7AA—C7—H7AB106.9H10D—C10A—H10F109.5
H7BC—C7—H7BD108.1H10E—C10A—H10F109.5
C8—C7—C6120.1 (5)H1D—O1—H1E106.8
C8—C7—H7AA107.3
N1—C4—C5—Cl1178.29 (17)C3—C4—C5—N2177.9 (2)
N1—C4—C5—N20.0 (2)C4—N1—C6—N20.4 (2)
N1—C6—C7—C875.8 (8)C4—N1—C6—C7177.11 (19)
N1—C6—C7—C8A101.2 (4)C5—N2—C6—N10.4 (2)
N2—C6—C7—C8100.3 (8)C5—N2—C6—C7177.0 (2)
N2—C6—C7—C8A75.0 (5)C6—N1—C4—C3178.42 (17)
N3—N4—C2—S1174.50 (13)C6—N1—C4—C50.2 (2)
N3—N4—C2—N54.4 (3)C6—N2—C5—Cl1178.66 (17)
N3—C3—C4—N13.0 (3)C6—N2—C5—C40.3 (2)
N3—C3—C4—C5174.6 (2)C6—C7—C8—C913 (2)
N4—N3—C3—C4177.68 (16)C6—C7—C8A—C9A72.0 (8)
C1—N5—C2—S10.5 (3)C7—C8—C9—C10146.0 (13)
C1—N5—C2—N4178.3 (2)C7—C8A—C9A—C10A172.9 (8)
C3—N3—N4—C2175.86 (17)C8—C7—C8A—C9A45.5 (17)
C3—C4—C5—Cl10.4 (4)C8A—C7—C8—C960.1 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1E···N20.851.942.790 (3)174
N1—H1···O1i0.861.972.832 (3)177
N5—H5···O1i0.862.303.114 (3)159
O1—H1D···S1ii0.852.513.345 (2)169
N4—H4···S1iii0.862.523.374 (2)169
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x1, y+1/2, z+1/2; (iii) x+3, y+1, z+2.
 

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