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The crystal packing of the hydrated title salt, C17H17N2OS+·Br·H2O, dominated by an extensive N—H...Owater, N—H...Br and Owater—H...Br hydrogen-bonding network between organic mol­ecules, bromine anions and water mol­ecules. The anions are located on crystallograpic twofold axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047428/sg2090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047428/sg2090Isup2.hkl
Contains datablock I

CCDC reference: 630458

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.086
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-amino-4-[4-(benzyloxy)phenyl]-5-methylthiazol-3-ium bromide monohydrate top
Crystal data top
C17H17N2OS+·Br·H2OF(000) = 1616
Mr = 395.31Dx = 1.483 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3021 reflections
a = 10.0462 (7) Åθ = 2.5–26.9°
b = 16.2513 (11) ŵ = 2.45 mm1
c = 21.7802 (15) ÅT = 294 K
β = 95.172 (1)°Block, yellow
V = 3541.4 (4) Å30.48 × 0.45 × 0.40 mm
Z = 8
Data collection top
Bruker AXS SMART 1000 CCD
diffractometer
3841 independent reflections
Radiation source: fine-focus sealed tube2494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1211
Tmin = 0.328, Tmax = 0.375k = 2019
8967 measured reflectionsl = 2724
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0329P)2 + 2.5508P]
where P = (Fo2 + 2Fc2)/3
3841 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. 1H NMR (CD3SOCD3, 400 MHz): δ 2.25 (s, 3H, CH3), 5.19 (s, 2H, OCH2), 7.16–7.49 (m, 9H, benzene ring), 8.99 (br, 2H, NH2), IR (KBr): 3381 (NH2), 1622 (CN), 1560 (CC), 1248 (C—O), 1176 (CS); MS (m/z): 296 (base, M+), 205 (M+–PhCH2), 91 (100%, PhCH2+), 80, 65, 51.

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 (Å2) top
xyzUiso*/Ueq
Br10.50000.64448 (2)0.25000.05594 (15)
Br21.00000.49680 (3)0.25000.06428 (17)
S10.66252 (8)0.20089 (4)0.30093 (4)0.0489 (2)
C10.7155 (3)0.29884 (15)0.28674 (13)0.0410 (6)
C20.5418 (3)0.23936 (17)0.34636 (13)0.0461 (7)
C30.5456 (3)0.32175 (16)0.34855 (12)0.0403 (6)
C40.4525 (4)0.17996 (19)0.37601 (18)0.0692 (10)
H4A0.49910.15780.41280.104*
H4B0.42770.13600.34780.104*
H4C0.37350.20810.38640.104*
C50.4656 (3)0.37937 (16)0.38233 (12)0.0400 (6)
C60.4390 (3)0.36381 (17)0.44232 (13)0.0479 (7)
H60.47060.31540.46120.057*
C70.3668 (3)0.41795 (18)0.47512 (14)0.0497 (7)
H70.35090.40620.51560.060*
C80.3184 (3)0.48970 (16)0.44736 (13)0.0427 (7)
C90.3454 (3)0.50712 (17)0.38729 (13)0.0479 (7)
H90.31440.55580.36870.057*
C100.4174 (3)0.45285 (16)0.35533 (13)0.0459 (7)
H100.43460.46510.31510.055*
C110.2104 (3)0.53075 (18)0.53612 (13)0.0502 (7)
H11A0.29140.52510.56360.060*
H11B0.16000.47990.53710.060*
C120.1284 (3)0.60127 (17)0.55641 (12)0.0430 (7)
C130.0116 (3)0.5877 (2)0.58276 (14)0.0569 (8)
H130.01910.53420.58670.068*
C140.0610 (4)0.6525 (2)0.60346 (16)0.0696 (10)
H140.13990.64230.62140.083*
C150.0176 (4)0.7316 (2)0.59771 (15)0.0656 (9)
H150.06730.77520.61130.079*
C160.1000 (4)0.74660 (19)0.57164 (14)0.0575 (8)
H160.13050.80030.56790.069*
C170.1725 (3)0.68160 (18)0.55105 (14)0.0516 (7)
H170.25170.69180.53340.062*
N10.6433 (2)0.35420 (13)0.31363 (10)0.0399 (5)
H1A0.65570.40630.30990.048*
N20.8139 (2)0.31619 (13)0.25239 (12)0.0527 (6)
H2A0.83500.36660.24620.063*
H2B0.85670.27710.23630.063*
O10.2431 (2)0.54728 (12)0.47458 (9)0.0510 (5)
O2W0.7215 (3)0.51472 (13)0.31481 (12)0.0613 (7)
H2C0.676 (4)0.549 (2)0.2987 (16)0.074*
H2D0.780 (4)0.518 (2)0.2934 (16)0.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0608 (3)0.0324 (2)0.0755 (3)0.0000.0111 (2)0.000
Br20.0675 (3)0.0392 (2)0.0902 (4)0.0000.0294 (3)0.000
S10.0555 (5)0.0273 (3)0.0642 (5)0.0005 (3)0.0063 (4)0.0025 (3)
C10.0456 (17)0.0323 (14)0.0443 (16)0.0039 (12)0.0009 (13)0.0010 (12)
C20.0496 (18)0.0344 (15)0.0543 (19)0.0039 (13)0.0049 (14)0.0006 (13)
C30.0407 (16)0.0328 (14)0.0471 (17)0.0012 (12)0.0014 (12)0.0034 (13)
C40.077 (2)0.0426 (17)0.091 (3)0.0179 (17)0.025 (2)0.0029 (18)
C50.0413 (16)0.0340 (14)0.0445 (17)0.0034 (11)0.0039 (12)0.0004 (12)
C60.0552 (19)0.0388 (16)0.0496 (18)0.0057 (14)0.0041 (14)0.0108 (14)
C70.0577 (19)0.0489 (17)0.0437 (17)0.0058 (15)0.0113 (14)0.0097 (14)
C80.0472 (17)0.0372 (15)0.0442 (17)0.0018 (13)0.0062 (13)0.0023 (13)
C90.063 (2)0.0352 (15)0.0462 (18)0.0075 (14)0.0082 (14)0.0085 (13)
C100.0572 (19)0.0378 (15)0.0436 (17)0.0016 (13)0.0088 (14)0.0045 (13)
C110.061 (2)0.0470 (17)0.0439 (18)0.0006 (14)0.0122 (14)0.0010 (14)
C120.0468 (17)0.0460 (16)0.0364 (16)0.0029 (13)0.0048 (13)0.0011 (13)
C130.057 (2)0.0564 (19)0.059 (2)0.0120 (16)0.0161 (16)0.0062 (16)
C140.059 (2)0.084 (3)0.068 (2)0.0034 (19)0.0234 (18)0.013 (2)
C150.076 (3)0.071 (2)0.050 (2)0.0171 (19)0.0056 (17)0.0147 (18)
C160.075 (2)0.0433 (17)0.053 (2)0.0010 (16)0.0011 (17)0.0022 (15)
C170.0529 (18)0.0511 (18)0.0515 (18)0.0042 (15)0.0086 (14)0.0045 (15)
N10.0448 (13)0.0259 (10)0.0494 (14)0.0021 (10)0.0061 (11)0.0035 (10)
N20.0571 (16)0.0332 (12)0.0703 (17)0.0059 (11)0.0197 (13)0.0009 (12)
O10.0692 (14)0.0425 (11)0.0435 (12)0.0071 (10)0.0169 (10)0.0031 (9)
O2W0.0577 (16)0.0394 (12)0.0888 (19)0.0007 (10)0.0174 (12)0.0107 (12)
Geometric parameters (Å, º) top
S1—C11.715 (3)C10—H100.9300
S1—C21.748 (3)C11—O11.434 (3)
C1—N21.322 (3)C11—C121.501 (4)
C1—N11.325 (3)C11—H11A0.9700
C2—C31.340 (4)C11—H11B0.9700
C2—C41.503 (4)C12—C131.370 (4)
C3—N11.398 (3)C12—C171.387 (4)
C3—C51.474 (4)C13—C141.379 (4)
C4—H4A0.9600C13—H130.9300
C4—H4B0.9600C14—C151.367 (5)
C4—H4C0.9600C14—H140.9300
C5—C61.380 (4)C15—C161.378 (5)
C5—C101.398 (4)C15—H150.9300
C6—C71.380 (4)C16—C171.380 (4)
C6—H60.9300C16—H160.9300
C7—C81.381 (4)C17—H170.9300
C7—H70.9300N1—H1A0.8600
C8—O11.371 (3)N2—H2A0.8600
C8—C91.389 (4)N2—H2B0.8600
C9—C101.370 (4)O2W—H2C0.78 (3)
C9—H90.9300O2W—H2D0.79 (3)
C1—S1—C290.73 (13)C5—C10—H10119.5
N2—C1—N1124.9 (2)O1—C11—C12108.1 (2)
N2—C1—S1124.0 (2)O1—C11—H11A110.1
N1—C1—S1111.0 (2)C12—C11—H11A110.1
C3—C2—C4130.0 (3)O1—C11—H11B110.1
C3—C2—S1111.0 (2)C12—C11—H11B110.1
C4—C2—S1119.0 (2)H11A—C11—H11B108.4
C2—C3—N1112.1 (2)C13—C12—C17118.6 (3)
C2—C3—C5129.6 (2)C13—C12—C11120.9 (3)
N1—C3—C5118.3 (2)C17—C12—C11120.4 (3)
C2—C4—H4A109.5C12—C13—C14120.8 (3)
C2—C4—H4B109.5C12—C13—H13119.6
H4A—C4—H4B109.5C14—C13—H13119.6
C2—C4—H4C109.5C15—C14—C13120.4 (3)
H4A—C4—H4C109.5C15—C14—H14119.8
H4B—C4—H4C109.5C13—C14—H14119.8
C6—C5—C10117.7 (3)C14—C15—C16119.7 (3)
C6—C5—C3121.1 (2)C14—C15—H15120.1
C10—C5—C3121.1 (2)C16—C15—H15120.1
C7—C6—C5121.9 (3)C15—C16—C17119.7 (3)
C7—C6—H6119.0C15—C16—H16120.1
C5—C6—H6119.0C17—C16—H16120.1
C6—C7—C8119.5 (3)C16—C17—C12120.8 (3)
C6—C7—H7120.3C16—C17—H17119.6
C8—C7—H7120.3C12—C17—H17119.6
O1—C8—C7124.9 (2)C1—N1—C3115.1 (2)
O1—C8—C9115.5 (2)C1—N1—H1A122.5
C7—C8—C9119.6 (3)C3—N1—H1A122.5
C10—C9—C8120.3 (3)C1—N2—H2A120.0
C10—C9—H9119.9C1—N2—H2B120.0
C8—C9—H9119.9H2A—N2—H2B120.0
C9—C10—C5121.0 (3)C8—O1—C11117.3 (2)
C9—C10—H10119.5H2C—O2W—H2D97 (4)
C2—S1—C1—N2179.8 (3)C6—C5—C10—C90.5 (4)
C2—S1—C1—N11.4 (2)C3—C5—C10—C9178.6 (3)
C1—S1—C2—C30.4 (2)O1—C11—C12—C13131.4 (3)
C1—S1—C2—C4179.7 (3)O1—C11—C12—C1751.1 (4)
C4—C2—C3—N1179.2 (3)C17—C12—C13—C140.1 (5)
S1—C2—C3—N10.7 (3)C11—C12—C13—C14177.6 (3)
C4—C2—C3—C52.0 (5)C12—C13—C14—C150.3 (5)
S1—C2—C3—C5178.1 (2)C13—C14—C15—C160.7 (5)
C2—C3—C5—C642.5 (4)C14—C15—C16—C170.6 (5)
N1—C3—C5—C6136.2 (3)C15—C16—C17—C120.2 (5)
C2—C3—C5—C10139.5 (3)C13—C12—C17—C160.2 (4)
N1—C3—C5—C1041.8 (4)C11—C12—C17—C16177.7 (3)
C10—C5—C6—C70.4 (4)N2—C1—N1—C3179.1 (3)
C3—C5—C6—C7178.5 (3)S1—C1—N1—C32.1 (3)
C5—C6—C7—C80.5 (5)C2—C3—N1—C11.9 (3)
C6—C7—C8—O1178.5 (3)C5—C3—N1—C1177.1 (2)
C6—C7—C8—C91.3 (4)C7—C8—O1—C111.2 (4)
O1—C8—C9—C10178.6 (3)C9—C8—O1—C11178.6 (3)
C7—C8—C9—C101.2 (4)C12—C11—O1—C8180.0 (2)
C8—C9—C10—C50.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2W0.861.882.724 (3)166
N2—H2A···Br20.862.683.483 (2)155
N2—H2B···Br1i0.862.593.362 (2)149
O2W—H2C···Br10.78 (3)2.52 (4)3.290 (2)171 (4)
O2W—H2D···Br20.79 (3)2.50 (4)3.259 (2)161 (4)
Symmetry code: (i) x+1/2, y1/2, z.
 

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