The components of the title compound, C
9H
9N
2Se
+·Br
−·H
2O, are linked to each other
via N—H
O, N—H
Br and O—H
Br hydrogen bonds.
Supporting information
CCDC reference: 289785
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.030
- wR factor = 0.077
- Data-to-parameter ratio = 20.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. Se1 .. 3.40 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for N11 - C1 .. 5.31 su
PLAT322_ALERT_2_C Check Hybridisation of Se1 in Main Residue . ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 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
3 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
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
2-Amino-4-phenylselenazolium bromide monohydrate
top
Crystal data top
C9H9N2Se+·Br−·H2O | F(000) = 624.00 |
Mr = 322.06 | Dx = 1.861 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 8209 reflections |
a = 11.493 (7) Å | θ = 3.3–27.5° |
b = 9.591 (5) Å | µ = 6.72 mm−1 |
c = 10.456 (4) Å | T = 296 K |
β = 94.211 (19)° | Platelet, colorless |
V = 1149.6 (10) Å3 | 0.24 × 0.18 × 0.08 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1834 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.054 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.263, Tmax = 0.584 | k = −12→12 |
10800 measured reflections | l = −12→13 |
2622 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.77σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.030 | (Δ/σ)max < 0.001 |
wR(F2) = 0.077 | Δρmax = 0.51 e Å−3 |
S = 1.00 | Δρmin = −0.60 e Å−3 |
2622 reflections | Extinction correction: Larson (1970) |
128 parameters | Extinction coefficient: 42 (7) |
H-atom parameters constrained | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.37518 (4) | 0.25588 (3) | −0.09385 (3) | 0.05395 (12) | |
Se1 | 0.59616 (3) | 0.09323 (3) | 0.14165 (3) | 0.04698 (11) | |
O1 | 0.7359 (2) | 0.5735 (2) | 0.3535 (2) | 0.0563 (7) | |
N11 | 0.5669 (2) | 0.3862 (2) | 0.1288 (2) | 0.0491 (8) | |
N12 | 0.6943 (2) | 0.2926 (2) | 0.2912 (2) | 0.0413 (7) | |
C1 | 0.6183 (3) | 0.2805 (3) | 0.1885 (2) | 0.0417 (9) | |
C2 | 0.7023 (3) | 0.0542 (3) | 0.2819 (2) | 0.0472 (10) | |
C3 | 0.7418 (2) | 0.1688 (3) | 0.3440 (2) | 0.0403 (9) | |
C4 | 0.8281 (2) | 0.1764 (3) | 0.4550 (2) | 0.0425 (9) | |
C5 | 0.8956 (3) | 0.2939 (3) | 0.4802 (2) | 0.0574 (11) | |
C6 | 0.9794 (3) | 0.2970 (4) | 0.5799 (3) | 0.0733 (14) | |
C7 | 0.9977 (3) | 0.1818 (4) | 0.6583 (3) | 0.0675 (13) | |
C8 | 0.9310 (3) | 0.0642 (4) | 0.6348 (3) | 0.0652 (13) | |
C9 | 0.8469 (3) | 0.0607 (3) | 0.5332 (2) | 0.0530 (11) | |
H101 | 0.7193 | 0.6082 | 0.2801 | 0.068* | |
H102 | 0.6973 | 0.6132 | 0.4081 | 0.067* | |
H2 | 0.7255 | −0.0356 | 0.3056 | 0.056* | |
H5 | 0.8839 | 0.3719 | 0.4280 | 0.068* | |
H6 | 1.0247 | 0.3764 | 0.5959 | 0.087* | |
H7 | 1.0546 | 0.1829 | 0.7263 | 0.080* | |
H8 | 0.9427 | −0.0131 | 0.6879 | 0.078* | |
H9 | 0.8029 | −0.0197 | 0.5177 | 0.064* | |
H111 | 0.5185 | 0.3716 | 0.0635 | 0.058* | |
H112 | 0.5811 | 0.4699 | 0.1549 | 0.058* | |
H121 | 0.7135 | 0.3727 | 0.3230 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0781 (3) | 0.0332 (2) | 0.0492 (2) | −0.00235 (18) | −0.00463 (19) | −0.00018 (12) |
Se1 | 0.0561 (2) | 0.0324 (2) | 0.0513 (2) | −0.00512 (17) | −0.00376 (17) | −0.00686 (12) |
O1 | 0.0747 (19) | 0.0432 (13) | 0.0504 (12) | 0.0025 (13) | 0.0008 (12) | −0.0045 (9) |
N11 | 0.064 (2) | 0.0303 (14) | 0.0498 (15) | −0.0007 (13) | −0.0153 (14) | −0.0011 (11) |
N12 | 0.0511 (19) | 0.0304 (13) | 0.0414 (13) | −0.0042 (12) | −0.0038 (12) | −0.0050 (10) |
C1 | 0.050 (2) | 0.0348 (16) | 0.0410 (16) | −0.0071 (15) | 0.0055 (15) | −0.0045 (12) |
C2 | 0.054 (2) | 0.0304 (16) | 0.0563 (19) | −0.0030 (16) | −0.0032 (17) | 0.0008 (13) |
C3 | 0.042 (2) | 0.0367 (17) | 0.0426 (16) | −0.0001 (15) | 0.0039 (14) | 0.0012 (12) |
C4 | 0.045 (2) | 0.0435 (18) | 0.0398 (16) | −0.0006 (16) | 0.0048 (15) | −0.0031 (13) |
C5 | 0.070 (2) | 0.051 (2) | 0.0493 (19) | −0.012 (2) | −0.0079 (18) | 0.0028 (15) |
C6 | 0.080 (3) | 0.072 (2) | 0.065 (2) | −0.016 (2) | −0.015 (2) | −0.007 (2) |
C7 | 0.067 (3) | 0.090 (3) | 0.043 (2) | 0.003 (2) | −0.0095 (19) | −0.0035 (19) |
C8 | 0.076 (3) | 0.074 (2) | 0.045 (2) | 0.016 (2) | 0.007 (2) | 0.0114 (18) |
C9 | 0.060 (2) | 0.048 (2) | 0.0517 (19) | −0.0014 (18) | 0.0060 (18) | 0.0047 (15) |
Geometric parameters (Å, º) top
Se1—C1 | 1.874 (2) | C8—C9 | 1.383 (4) |
Se1—C2 | 1.875 (3) | O1—H102 | 0.840 |
N11—C1 | 1.309 (3) | O1—H101 | 0.845 |
N12—C1 | 1.338 (3) | N11—H111 | 0.860 |
N12—C3 | 1.403 (3) | N11—H112 | 0.860 |
C2—C3 | 1.339 (4) | N12—H121 | 0.860 |
C3—C4 | 1.472 (4) | C2—H2 | 0.930 |
C4—C5 | 1.383 (4) | C5—H5 | 0.930 |
C4—C9 | 1.386 (4) | C6—H6 | 0.930 |
C5—C6 | 1.367 (5) | C7—H7 | 0.930 |
C6—C7 | 1.383 (5) | C8—H8 | 0.930 |
C7—C8 | 1.376 (6) | C9—H9 | 0.930 |
| | | |
Br1···Se1i | 3.405 (2) | H2···Br1i | 3.214 |
Br1···O1ii | 3.388 (2) | H2···N11ii | 3.559 |
Br1···O1iii | 3.342 (2) | H2···C7viii | 3.472 |
Br1···N11 | 3.330 (2) | H2···H102xii | 3.557 |
Br1···N11iii | 3.521 (2) | H2···H101xii | 3.427 |
Se1···Br1i | 3.405 (2) | H2···H7viii | 2.936 |
O1···Br1iv | 3.388 (2) | H2···H111ii | 3.330 |
O1···Br1iii | 3.342 (2) | H2···H112ii | 3.578 |
O1···N11 | 3.442 (3) | H101···Br1iii | 2.522 |
O1···N12 | 2.805 (3) | H101···N11 | 3.114 |
O1···C1 | 3.515 (3) | H101···N12 | 3.044 |
O1···C5 | 3.458 (4) | H101···C1 | 3.461 |
O1···C6v | 3.521 (5) | H101···C8vi | 3.392 |
O1···C8vi | 3.572 (4) | H101···C9vi | 3.464 |
N11···Br1 | 3.330 (2) | H101···H2xi | 3.427 |
N11···Br1iii | 3.521 (2) | H101···H5 | 3.267 |
N11···O1 | 3.442 (3) | H101···H6v | 3.130 |
N11···C9vi | 3.477 (4) | H101···H7v | 3.286 |
N12···O1 | 2.805 (3) | H101···H8vi | 2.953 |
N12···C8vi | 3.552 (4) | H101···H9vi | 3.091 |
C1···O1 | 3.515 (3) | H101···H112 | 2.386 |
C1···C4vi | 3.580 (4) | H101···H121 | 2.305 |
C1···C9vi | 3.535 (4) | H5···O1 | 2.654 |
C4···C1vii | 3.580 (4) | H5···C6v | 3.546 |
C5···O1 | 3.458 (4) | H5···C7vi | 3.235 |
C6···O1v | 3.521 (5) | H5···C8vi | 3.211 |
C8···O1vii | 3.572 (4) | H5···H102 | 3.152 |
C8···N12vii | 3.552 (4) | H5···H101 | 3.267 |
C8···C8viii | 3.554 (5) | H5···H6v | 2.652 |
C8···C9viii | 3.419 (5) | H5···H7vi | 3.030 |
C9···N11vii | 3.477 (4) | H5···H8vi | 2.973 |
C9···C1vii | 3.535 (4) | H6···O1v | 2.806 |
C9···C8viii | 3.419 (5) | H6···C5v | 3.403 |
Br1···H102ii | 2.564 | H6···C8ix | 3.350 |
Br1···H102iii | 3.559 | H6···H102v | 3.200 |
Br1···H2i | 3.214 | H6···H101v | 3.130 |
Br1···H101iii | 2.522 | H6···H5v | 2.652 |
Br1···H9iv | 3.113 | H6···H6v | 3.131 |
Br1···H111 | 2.501 | H6···H8ix | 2.500 |
Br1···H112iii | 2.761 | H7···O1v | 3.500 |
Se1···H102ii | 3.380 | H7···C5vii | 3.339 |
Se1···H102vi | 3.413 | H7···H2viii | 2.936 |
Se1···H112ii | 3.273 | H7···H101v | 3.286 |
O1···H5 | 2.654 | H7···H5vii | 3.030 |
O1···H6v | 2.806 | H7···H8ix | 3.051 |
O1···H7v | 3.500 | H7···H9viii | 3.501 |
O1···H8vi | 3.097 | H8···O1vii | 3.097 |
O1···H112 | 2.814 | H8···C4viii | 3.493 |
O1···H121 | 1.966 | H8···C6x | 3.114 |
N11···H2iv | 3.559 | H8···C7x | 3.385 |
N11···H101 | 3.114 | H8···C9viii | 3.495 |
N11···H9vi | 3.287 | H8···H101vii | 2.953 |
N11···H111iii | 3.180 | H8···H5vii | 2.973 |
N11···H112iii | 3.586 | H8···H6x | 2.500 |
N12···H102 | 3.309 | H8···H7x | 3.051 |
N12···H101 | 3.044 | H8···H121vii | 3.361 |
C1···H101 | 3.461 | H9···Br1ii | 3.113 |
C2···H111ii | 3.567 | H9···N11vii | 3.287 |
C2···H112ii | 3.466 | H9···C7viii | 3.417 |
C3···H111vii | 3.587 | H9···C8viii | 3.577 |
C4···H8viii | 3.493 | H9···H101vii | 3.091 |
C5···H6v | 3.403 | H9···H7viii | 3.501 |
C5···H7vi | 3.339 | H9···H112vii | 3.053 |
C6···H5v | 3.546 | H111···Br1 | 2.501 |
C6···H8ix | 3.114 | H111···N11iii | 3.180 |
C7···H2viii | 3.472 | H111···C2iv | 3.567 |
C7···H5vii | 3.235 | H111···C3vi | 3.587 |
C7···H8ix | 3.385 | H111···H102ii | 3.535 |
C7···H9viii | 3.417 | H111···H2iv | 3.330 |
C8···H101vii | 3.392 | H111···H111iii | 2.816 |
C8···H5vii | 3.211 | H111···H112iii | 2.907 |
C8···H6x | 3.350 | H112···Br1iii | 2.761 |
C8···H9viii | 3.577 | H112···Se1iv | 3.273 |
C8···H121vii | 3.348 | H112···O1 | 2.814 |
C9···H101vii | 3.464 | H112···N11iii | 3.586 |
C9···H8viii | 3.495 | H112···C2iv | 3.466 |
C9···H112vii | 3.408 | H112···C9vi | 3.408 |
C9···H121vii | 3.554 | H112···H102 | 3.188 |
H102···Br1iv | 2.564 | H112···H2iv | 3.578 |
H102···Br1iii | 3.559 | H112···H101 | 2.386 |
H102···Se1iv | 3.380 | H112···H9vi | 3.053 |
H102···Se1vii | 3.413 | H112···H111iii | 2.907 |
H102···N12 | 3.309 | H121···O1 | 1.966 |
H102···H2xi | 3.557 | H121···C8vi | 3.348 |
H102···H5 | 3.152 | H121···C9vi | 3.554 |
H102···H6v | 3.200 | H121···H102 | 2.484 |
H102···H111iv | 3.535 | H121···H101 | 2.305 |
H102···H112 | 3.188 | H121···H8vi | 3.361 |
H102···H121 | 2.484 | | |
| | | |
C1—Se1—C2 | 85.34 (13) | C1—N11—H111 | 119.7 |
C1—N12—C3 | 117.0 (2) | C1—N11—H112 | 120.3 |
Se1—C1—N11 | 124.7 (2) | H111—N11—H112 | 120.0 |
Se1—C1—N12 | 111.2 (2) | C1—N12—H121 | 121.5 |
N11—C1—N12 | 124.1 (2) | C3—N12—H121 | 121.5 |
Se1—C2—C3 | 113.2 (2) | Se1—C2—H2 | 123.4 |
N12—C3—C2 | 113.3 (2) | C3—C2—H2 | 123.4 |
N12—C3—C4 | 119.3 (2) | C4—C5—H5 | 119.3 |
C2—C3—C4 | 127.4 (2) | C6—C5—H5 | 119.6 |
C3—C4—C5 | 121.8 (2) | C5—C6—H6 | 120.6 |
C3—C4—C9 | 119.5 (2) | C7—C6—H6 | 119.3 |
C5—C4—C9 | 118.7 (2) | C6—C7—H7 | 120.8 |
C4—C5—C6 | 121.1 (3) | C8—C7—H7 | 119.8 |
C5—C6—C7 | 120.2 (3) | C7—C8—H8 | 119.5 |
C6—C7—C8 | 119.4 (3) | C9—C8—H8 | 120.1 |
C7—C8—C9 | 120.4 (3) | C4—C9—H9 | 120.2 |
C4—C9—C8 | 120.2 (3) | C8—C9—H9 | 119.6 |
H102—O1—H101 | 110.1 | | |
| | | |
C1—Se1—C2—C3 | −0.6 (2) | C2—C3—C4—C5 | 154.1 (3) |
C2—Se1—C1—N11 | −179.9 (2) | C2—C3—C4—C9 | −22.6 (5) |
C2—Se1—C1—N12 | 0.4 (2) | C3—C4—C5—C6 | −176.7 (3) |
C1—N12—C3—C2 | −0.2 (4) | C3—C4—C9—C8 | 177.4 (3) |
C1—N12—C3—C4 | 178.5 (2) | C5—C4—C9—C8 | 0.6 (5) |
C3—N12—C1—Se1 | −0.3 (3) | C9—C4—C5—C6 | −0.0 (5) |
C3—N12—C1—N11 | −179.9 (2) | C4—C5—C6—C7 | −0.4 (6) |
Se1—C2—C3—N12 | 0.5 (3) | C5—C6—C7—C8 | 0.2 (5) |
Se1—C2—C3—C4 | −178.0 (2) | C6—C7—C8—C9 | 0.4 (6) |
N12—C3—C4—C5 | −24.4 (4) | C7—C8—C9—C4 | −0.8 (5) |
N12—C3—C4—C9 | 158.9 (3) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y+1/2, −z+1/2; (v) −x+2, −y+1, −z+1; (vi) x, −y+1/2, z−1/2; (vii) x, −y+1/2, z+1/2; (viii) −x+2, −y, −z+1; (ix) −x+2, y+1/2, −z+3/2; (x) −x+2, y−1/2, −z+3/2; (xi) x, y+1, z; (xii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H121···O1 | 0.86 | 1.97 | 2.805 (3) | 165 |
N11—H111···Br1 | 0.86 | 2.50 | 3.330 (3) | 162 |
N11—H112···Br1iii | 0.86 | 2.76 | 3.521 (3) | 148 |
O1—H101···Br1iii | 0.85 | 2.52 | 3.342 (2) | 164 |
O1—H102···Br1iv | 0.84 | 2.56 | 3.388 (3) | 167 |
Symmetry codes: (iii) −x+1, −y+1, −z; (iv) −x+1, y+1/2, −z+1/2. |