2-Amino-4-[4-(benz­yloxy)phen­yl]-5-methyl­thia­zol-3-ium bromide monohydrate

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

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

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

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

Crystal data

C17H17N2OS^+·Br^−·H2O	F(000) = 1616
Mr = 395.31	Dx = 1.483 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3021 reflections
a = 10.0462 (7) Å	θ = 2.5–26.9°
b = 16.2513 (11) Å	µ = 2.45 mm^−1
c = 21.7802 (15) Å	T = 294 K
β = 95.172 (1)°	Block, yellow
V = 3541.4 (4) Å^3	0.48 × 0.45 × 0.40 mm
Z = 8

Data collection

Bruker AXS SMART 1000 CCD diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	2494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.328, Tmax = 0.375	k = −20→19
8967 measured reflections	l = −27→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 2.5508P] where P = (Fo^2 + 2Fc^2)/3
3841 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (C═N), 1560 (C═C), 1248 (C—O), 1176 (C═S); 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.5000	0.64448 (2)	0.2500	0.05594 (15)
Br2	1.0000	0.49680 (3)	0.2500	0.06428 (17)
S1	0.66252 (8)	0.20089 (4)	0.30093 (4)	0.0489 (2)
C1	0.7155 (3)	0.29884 (15)	0.28674 (13)	0.0410 (6)
C2	0.5418 (3)	0.23936 (17)	0.34636 (13)	0.0461 (7)
C3	0.5456 (3)	0.32175 (16)	0.34855 (12)	0.0403 (6)
C4	0.4525 (4)	0.17996 (19)	0.37601 (18)	0.0692 (10)
H4A	0.4991	0.1578	0.4128	0.104*
H4B	0.4277	0.1360	0.3478	0.104*
H4C	0.3735	0.2081	0.3864	0.104*
C5	0.4656 (3)	0.37937 (16)	0.38233 (12)	0.0400 (6)
C6	0.4390 (3)	0.36381 (17)	0.44232 (13)	0.0479 (7)
H6	0.4706	0.3154	0.4612	0.057*
C7	0.3668 (3)	0.41795 (18)	0.47512 (14)	0.0497 (7)
H7	0.3509	0.4062	0.5156	0.060*
C8	0.3184 (3)	0.48970 (16)	0.44736 (13)	0.0427 (7)
C9	0.3454 (3)	0.50712 (17)	0.38729 (13)	0.0479 (7)
H9	0.3144	0.5558	0.3687	0.057*
C10	0.4174 (3)	0.45285 (16)	0.35533 (13)	0.0459 (7)
H10	0.4346	0.4651	0.3151	0.055*
C11	0.2104 (3)	0.53075 (18)	0.53612 (13)	0.0502 (7)
H11A	0.2914	0.5251	0.5636	0.060*
H11B	0.1600	0.4799	0.5371	0.060*
C12	0.1284 (3)	0.60127 (17)	0.55641 (12)	0.0430 (7)
C13	0.0116 (3)	0.5877 (2)	0.58276 (14)	0.0569 (8)
H13	−0.0191	0.5342	0.5867	0.068*
C14	−0.0610 (4)	0.6525 (2)	0.60346 (16)	0.0696 (10)
H14	−0.1399	0.6423	0.6214	0.083*
C15	−0.0176 (4)	0.7316 (2)	0.59771 (15)	0.0656 (9)
H15	−0.0673	0.7752	0.6113	0.079*
C16	0.1000 (4)	0.74660 (19)	0.57164 (14)	0.0575 (8)
H16	0.1305	0.8003	0.5679	0.069*
C17	0.1725 (3)	0.68160 (18)	0.55105 (14)	0.0516 (7)
H17	0.2517	0.6918	0.5334	0.062*
N1	0.6433 (2)	0.35420 (13)	0.31363 (10)	0.0399 (5)
H1A	0.6557	0.4063	0.3099	0.048*
N2	0.8139 (2)	0.31619 (13)	0.25239 (12)	0.0527 (6)
H2A	0.8350	0.3666	0.2462	0.063*
H2B	0.8567	0.2771	0.2363	0.063*
O1	0.2431 (2)	0.54728 (12)	0.47458 (9)	0.0510 (5)
O2W	0.7215 (3)	0.51472 (13)	0.31481 (12)	0.0613 (7)
H2C	0.676 (4)	0.549 (2)	0.2987 (16)	0.074*
H2D	0.780 (4)	0.518 (2)	0.2934 (16)	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0608 (3)	0.0324 (2)	0.0755 (3)	0.000	0.0111 (2)	0.000
Br2	0.0675 (3)	0.0392 (2)	0.0902 (4)	0.000	0.0294 (3)	0.000
S1	0.0555 (5)	0.0273 (3)	0.0642 (5)	−0.0005 (3)	0.0063 (4)	−0.0025 (3)
C1	0.0456 (17)	0.0323 (14)	0.0443 (16)	0.0039 (12)	−0.0009 (13)	0.0010 (12)
C2	0.0496 (18)	0.0344 (15)	0.0543 (19)	−0.0039 (13)	0.0049 (14)	0.0006 (13)
C3	0.0407 (16)	0.0328 (14)	0.0471 (17)	0.0012 (12)	0.0014 (12)	0.0034 (13)
C4	0.077 (2)	0.0426 (17)	0.091 (3)	−0.0179 (17)	0.025 (2)	−0.0029 (18)
C5	0.0413 (16)	0.0340 (14)	0.0445 (17)	−0.0034 (11)	0.0039 (12)	0.0004 (12)
C6	0.0552 (19)	0.0388 (16)	0.0496 (18)	0.0057 (14)	0.0041 (14)	0.0108 (14)
C7	0.0577 (19)	0.0489 (17)	0.0437 (17)	0.0058 (15)	0.0113 (14)	0.0097 (14)
C8	0.0472 (17)	0.0372 (15)	0.0442 (17)	−0.0018 (13)	0.0062 (13)	−0.0023 (13)
C9	0.063 (2)	0.0352 (15)	0.0462 (18)	0.0075 (14)	0.0082 (14)	0.0085 (13)
C10	0.0572 (19)	0.0378 (15)	0.0436 (17)	−0.0016 (13)	0.0088 (14)	0.0045 (13)
C11	0.061 (2)	0.0470 (17)	0.0439 (18)	−0.0006 (14)	0.0122 (14)	0.0010 (14)
C12	0.0468 (17)	0.0460 (16)	0.0364 (16)	−0.0029 (13)	0.0048 (13)	−0.0011 (13)
C13	0.057 (2)	0.0564 (19)	0.059 (2)	−0.0120 (16)	0.0161 (16)	−0.0062 (16)
C14	0.059 (2)	0.084 (3)	0.068 (2)	−0.0034 (19)	0.0234 (18)	−0.013 (2)
C15	0.076 (3)	0.071 (2)	0.050 (2)	0.0171 (19)	0.0056 (17)	−0.0147 (18)
C16	0.075 (2)	0.0433 (17)	0.053 (2)	0.0010 (16)	−0.0011 (17)	−0.0022 (15)
C17	0.0529 (18)	0.0511 (18)	0.0515 (18)	−0.0042 (15)	0.0086 (14)	0.0045 (15)
N1	0.0448 (13)	0.0259 (10)	0.0494 (14)	0.0021 (10)	0.0061 (11)	0.0035 (10)
N2	0.0571 (16)	0.0332 (12)	0.0703 (17)	0.0059 (11)	0.0197 (13)	−0.0009 (12)
O1	0.0692 (14)	0.0425 (11)	0.0435 (12)	0.0071 (10)	0.0169 (10)	0.0031 (9)
O2W	0.0577 (16)	0.0394 (12)	0.0888 (19)	0.0007 (10)	0.0174 (12)	0.0107 (12)

Geometric parameters (Å, º)

S1—C1	1.715 (3)	C10—H10	0.9300
S1—C2	1.748 (3)	C11—O1	1.434 (3)
C1—N2	1.322 (3)	C11—C12	1.501 (4)
C1—N1	1.325 (3)	C11—H11A	0.9700
C2—C3	1.340 (4)	C11—H11B	0.9700
C2—C4	1.503 (4)	C12—C13	1.370 (4)
C3—N1	1.398 (3)	C12—C17	1.387 (4)
C3—C5	1.474 (4)	C13—C14	1.379 (4)
C4—H4A	0.9600	C13—H13	0.9300
C4—H4B	0.9600	C14—C15	1.367 (5)
C4—H4C	0.9600	C14—H14	0.9300
C5—C6	1.380 (4)	C15—C16	1.378 (5)
C5—C10	1.398 (4)	C15—H15	0.9300
C6—C7	1.380 (4)	C16—C17	1.380 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.381 (4)	C17—H17	0.9300
C7—H7	0.9300	N1—H1A	0.8600
C8—O1	1.371 (3)	N2—H2A	0.8600
C8—C9	1.389 (4)	N2—H2B	0.8600
C9—C10	1.370 (4)	O2W—H2C	0.78 (3)
C9—H9	0.9300	O2W—H2D	0.79 (3)
C1—S1—C2	90.73 (13)	C5—C10—H10	119.5
N2—C1—N1	124.9 (2)	O1—C11—C12	108.1 (2)
N2—C1—S1	124.0 (2)	O1—C11—H11A	110.1
N1—C1—S1	111.0 (2)	C12—C11—H11A	110.1
C3—C2—C4	130.0 (3)	O1—C11—H11B	110.1
C3—C2—S1	111.0 (2)	C12—C11—H11B	110.1
C4—C2—S1	119.0 (2)	H11A—C11—H11B	108.4
C2—C3—N1	112.1 (2)	C13—C12—C17	118.6 (3)
C2—C3—C5	129.6 (2)	C13—C12—C11	120.9 (3)
N1—C3—C5	118.3 (2)	C17—C12—C11	120.4 (3)
C2—C4—H4A	109.5	C12—C13—C14	120.8 (3)
C2—C4—H4B	109.5	C12—C13—H13	119.6
H4A—C4—H4B	109.5	C14—C13—H13	119.6
C2—C4—H4C	109.5	C15—C14—C13	120.4 (3)
H4A—C4—H4C	109.5	C15—C14—H14	119.8
H4B—C4—H4C	109.5	C13—C14—H14	119.8
C6—C5—C10	117.7 (3)	C14—C15—C16	119.7 (3)
C6—C5—C3	121.1 (2)	C14—C15—H15	120.1
C10—C5—C3	121.1 (2)	C16—C15—H15	120.1
C7—C6—C5	121.9 (3)	C15—C16—C17	119.7 (3)
C7—C6—H6	119.0	C15—C16—H16	120.1
C5—C6—H6	119.0	C17—C16—H16	120.1
C6—C7—C8	119.5 (3)	C16—C17—C12	120.8 (3)
C6—C7—H7	120.3	C16—C17—H17	119.6
C8—C7—H7	120.3	C12—C17—H17	119.6
O1—C8—C7	124.9 (2)	C1—N1—C3	115.1 (2)
O1—C8—C9	115.5 (2)	C1—N1—H1A	122.5
C7—C8—C9	119.6 (3)	C3—N1—H1A	122.5
C10—C9—C8	120.3 (3)	C1—N2—H2A	120.0
C10—C9—H9	119.9	C1—N2—H2B	120.0
C8—C9—H9	119.9	H2A—N2—H2B	120.0
C9—C10—C5	121.0 (3)	C8—O1—C11	117.3 (2)
C9—C10—H10	119.5	H2C—O2W—H2D	97 (4)
C2—S1—C1—N2	179.8 (3)	C6—C5—C10—C9	−0.5 (4)
C2—S1—C1—N1	−1.4 (2)	C3—C5—C10—C9	−178.6 (3)
C1—S1—C2—C3	0.4 (2)	O1—C11—C12—C13	131.4 (3)
C1—S1—C2—C4	−179.7 (3)	O1—C11—C12—C17	−51.1 (4)
C4—C2—C3—N1	−179.2 (3)	C17—C12—C13—C14	0.1 (5)
S1—C2—C3—N1	0.7 (3)	C11—C12—C13—C14	177.6 (3)
C4—C2—C3—C5	2.0 (5)	C12—C13—C14—C15	0.3 (5)
S1—C2—C3—C5	−178.1 (2)	C13—C14—C15—C16	−0.7 (5)
C2—C3—C5—C6	42.5 (4)	C14—C15—C16—C17	0.6 (5)
N1—C3—C5—C6	−136.2 (3)	C15—C16—C17—C12	−0.2 (5)
C2—C3—C5—C10	−139.5 (3)	C13—C12—C17—C16	−0.2 (4)
N1—C3—C5—C10	41.8 (4)	C11—C12—C17—C16	−177.7 (3)
C10—C5—C6—C7	0.4 (4)	N2—C1—N1—C3	−179.1 (3)
C3—C5—C6—C7	178.5 (3)	S1—C1—N1—C3	2.1 (3)
C5—C6—C7—C8	0.5 (5)	C2—C3—N1—C1	−1.9 (3)
C6—C7—C8—O1	178.5 (3)	C5—C3—N1—C1	177.1 (2)
C6—C7—C8—C9	−1.3 (4)	C7—C8—O1—C11	−1.2 (4)
O1—C8—C9—C10	−178.6 (3)	C9—C8—O1—C11	178.6 (3)
C7—C8—C9—C10	1.2 (4)	C12—C11—O1—C8	180.0 (2)
C8—C9—C10—C5	−0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2W	0.86	1.88	2.724 (3)	166
N2—H2A···Br2	0.86	2.68	3.483 (2)	155
N2—H2B···Br1^i	0.86	2.59	3.362 (2)	149
O2W—H2C···Br1	0.78 (3)	2.52 (4)	3.290 (2)	171 (4)
O2W—H2D···Br2	0.79 (3)	2.50 (4)	3.259 (2)	161 (4)

Symmetry code: (i) x+1/2, y−1/2, z.