1-(6-Bromo­pyridin-2-yl)-3-methyl-3H-imidazol-1-ium bromide monohydrate

The structure of the title compound, C₉H₉BrN₃⁺·Br^-·H₂O, was determined at 150 K. It is a supramolecular adduct of imidazolium bromide and water mol­ecules. Helical chains of (H₂O·Br^-) exist in the structure along the [001] direction. Each chain forms extensive hydrogen bonds with the imidazolium cations.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.035
• wR factor = 0.097
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.45 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  O1      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  O1      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O1      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4C    ..  BR1     ..       3.03 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.73
           From the CIF: _reflns_number_total               2877
           Count of symmetry unique reflns         1619
           Completeness (_total/calc)            177.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1258
           Fraction of Friedel pairs measured     0.777
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2004) and SMART (Bruker, 2004); cell refinement: APEX2 and SAINT; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(6-Bromopyridin-2-yl)-3-methyl-3H-imidzol-1-ium bromide monoydrate

Crystal data

C9H9BrN3^+·Br^−·H2O	F(000) = 656
Mr = 337.03	Dx = 1.897 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4258 reflections
a = 7.1233 (3) Å	θ = 2.3–27.8°
b = 17.3399 (7) Å	µ = 6.85 mm^−1
c = 9.5533 (4) Å	T = 150 K
V = 1180.00 (8) Å^3	Plate, colorless
Z = 4	0.23 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX-II diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	2522 reflections with I > 2σ
Graphite monochromator	Rint = 0.047
ω scans	θmax = 28.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.237, Tmax = 0.334	k = −23→23
11417 measured reflections	l = −12→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0545P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2877 reflections	Δρmax = 0.84 e Å^−3
145 parameters	Δρmin = −0.64 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.042 (16)

Special details

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	0.30233 (6)	0.19841 (3)	−0.23207 (5)	0.02620 (13)
Br2	0.13404 (6)	0.07940 (3)	0.50740 (6)	0.02505 (13)
C1	0.5194 (6)	0.1122 (3)	0.2560 (6)	0.0223 (9)
H1	0.4801	0.0842	0.1756	0.027*
C2	0.6288 (6)	0.1404 (3)	0.4649 (5)	0.0237 (11)
H2	0.6796	0.1343	0.5562	0.028*
C3	0.5812 (7)	0.2072 (3)	0.4043 (6)	0.0259 (11)
H3	0.5926	0.2573	0.4436	0.031*
C4	0.6190 (9)	−0.0011 (3)	0.3931 (7)	0.0352 (13)
H4A	0.5138	−0.0220	0.4473	0.053*
H4B	0.7364	−0.0096	0.4443	0.053*
H4C	0.6254	−0.0272	0.3022	0.053*
C5	0.4580 (6)	0.2409 (3)	0.1619 (5)	0.0183 (9)
C6	0.4615 (6)	0.3201 (3)	0.1818 (6)	0.0235 (10)
H6	0.4980	0.3425	0.2684	0.028*
C7	0.4083 (7)	0.3653 (3)	0.0668 (6)	0.0266 (11)
H7	0.4064	0.4199	0.0740	0.032*
C8	0.3583 (7)	0.3296 (3)	−0.0574 (6)	0.0264 (11)
H8	0.3216	0.3592	−0.1365	0.032*
C9	0.3632 (6)	0.2503 (3)	−0.0637 (6)	0.0208 (10)
H10	0.101 (11)	−0.028 (4)	0.177 (9)	0.05 (2)*
H11	0.166 (10)	0.009 (4)	0.294 (11)	0.06 (2)*
N1	0.5912 (6)	0.0821 (2)	0.3714 (5)	0.0223 (9)
N2	0.5116 (5)	0.1888 (2)	0.2721 (5)	0.0189 (7)
N3	0.4096 (5)	0.2052 (2)	0.0429 (4)	0.0185 (8)
O1	0.2111 (5)	−0.0199 (2)	0.2153 (4)	0.0311 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0303 (2)	0.0300 (2)	0.0183 (2)	0.00259 (19)	−0.0024 (2)	−0.0006 (2)
Br2	0.0293 (2)	0.0249 (2)	0.0210 (2)	−0.00332 (18)	0.0014 (2)	0.0006 (2)
C1	0.023 (2)	0.027 (2)	0.017 (2)	−0.0031 (17)	−0.001 (2)	0.003 (2)
C2	0.023 (2)	0.029 (3)	0.020 (3)	−0.0007 (19)	−0.0023 (17)	−0.004 (2)
C3	0.021 (2)	0.038 (3)	0.019 (3)	0.001 (2)	−0.0017 (18)	−0.002 (2)
C4	0.045 (3)	0.030 (3)	0.031 (3)	0.001 (2)	−0.009 (2)	0.007 (3)
C5	0.017 (2)	0.023 (2)	0.016 (2)	−0.0013 (17)	0.0013 (16)	0.0020 (19)
C6	0.021 (2)	0.022 (2)	0.027 (3)	0.0003 (18)	0.0015 (19)	−0.002 (2)
C7	0.029 (3)	0.022 (2)	0.029 (3)	0.004 (2)	0.002 (2)	0.002 (2)
C8	0.030 (3)	0.022 (3)	0.027 (3)	0.005 (2)	0.000 (2)	0.006 (2)
C9	0.019 (2)	0.026 (3)	0.017 (2)	−0.0016 (19)	0.0010 (17)	−0.0043 (19)
N1	0.0242 (19)	0.026 (2)	0.016 (2)	0.0031 (16)	−0.0027 (16)	0.0007 (18)
N2	0.0193 (15)	0.0212 (16)	0.0163 (18)	0.0005 (13)	0.0011 (18)	−0.0001 (18)
N3	0.0168 (16)	0.0197 (18)	0.019 (2)	0.0008 (14)	0.0006 (14)	0.0008 (16)
O1	0.032 (2)	0.037 (2)	0.025 (2)	0.0001 (17)	−0.0022 (16)	−0.0055 (17)

Geometric parameters (Å, º)

Br1—C9	1.893 (5)	C5—N3	1.339 (6)
C1—N1	1.323 (7)	C5—C6	1.386 (6)
C1—N2	1.338 (5)	C5—N2	1.440 (6)
C1—H1	0.9500	C6—C7	1.401 (7)
C2—C3	1.339 (8)	C6—H6	0.9500
C2—N1	1.375 (7)	C7—C8	1.384 (8)
C2—H2	0.9500	C7—H7	0.9500
C3—N2	1.394 (7)	C8—C9	1.378 (7)
C3—H3	0.9500	C8—H8	0.9500
C4—N1	1.472 (7)	C9—N3	1.326 (7)
C4—H4A	0.9800	O1—H10	0.88 (8)
C4—H4B	0.9800	O1—H11	0.96 (10)
C4—H4C	0.9800
N1—C1—N2	108.1 (5)	C5—C6—H6	121.9
N1—C1—H1	125.9	C7—C6—H6	121.9
N2—C1—H1	125.9	C8—C7—C6	119.5 (5)
C3—C2—N1	107.8 (4)	C8—C7—H7	120.2
C3—C2—H2	126.1	C6—C7—H7	120.2
N1—C2—H2	126.1	C9—C8—C7	118.5 (5)
C2—C3—N2	106.4 (5)	C9—C8—H8	120.8
C2—C3—H3	126.8	C7—C8—H8	120.8
N2—C3—H3	126.8	N3—C9—C8	124.2 (5)
N1—C4—H4A	109.5	N3—C9—Br1	115.5 (4)
N1—C4—H4B	109.5	C8—C9—Br1	120.4 (4)
H4A—C4—H4B	109.5	C1—N1—C2	109.1 (4)
N1—C4—H4C	109.5	C1—N1—C4	123.8 (5)
H4A—C4—H4C	109.5	C2—N1—C4	127.1 (4)
H4B—C4—H4C	109.5	C1—N2—C3	108.5 (4)
N3—C5—C6	125.4 (4)	C1—N2—C5	123.4 (5)
N3—C5—N2	113.5 (4)	C3—N2—C5	127.8 (4)
C6—C5—N2	121.1 (4)	C9—N3—C5	116.3 (4)
C5—C6—C7	116.2 (5)	H10—O1—H11	96 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···Br2	0.96 (10)	2.38 (10)	3.324 (4)	165 (6)
C1—H1···O1	0.95	2.66	3.196 (6)	116
C3—H3···Br2^i	0.95	2.91	3.847 (6)	168
C6—H6···Br2^i	0.95	2.83	3.771 (5)	173
C8—H8···O1^ii	0.95	2.54	3.431 (7)	156
C7—H7···Br2^ii	0.95	2.85	3.768 (5)	162
C4—H4B···O1^iii	0.98	2.66	3.327 (8)	125
C2—H2···O1^iii	0.95	2.62	3.375 (6)	136
C4—H4C···Br1^iii	0.98	3.03	3.667 (6)	124

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+1/2, y+1/2, z−1/2; (iii) −x+1, −y, z+1/2.