2-Amino-4-phenyl­selenazolium bromide monohydrate

The components of the title compound, C₉H₉N₂Se⁺·Br⁻·H₂O, are linked to each other via N—H...O, N—H...Br and O—H...Br hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.24 × 0.18 × 0.08 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1834 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	w = 1/[0.77σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.030	(Δ/σ)max < 0.001
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···Se1^i	3.405 (2)	H2···Br1^i	3.214
Br1···O1^ii	3.388 (2)	H2···N11^ii	3.559
Br1···O1^iii	3.342 (2)	H2···C7^viii	3.472
Br1···N11	3.330 (2)	H2···H102^xii	3.557
Br1···N11^iii	3.521 (2)	H2···H101^xii	3.427
Se1···Br1^i	3.405 (2)	H2···H7^viii	2.936
O1···Br1^iv	3.388 (2)	H2···H111^ii	3.330
O1···Br1^iii	3.342 (2)	H2···H112^ii	3.578
O1···N11	3.442 (3)	H101···Br1^iii	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···C6^v	3.521 (5)	H101···C8^vi	3.392
O1···C8^vi	3.572 (4)	H101···C9^vi	3.464
N11···Br1	3.330 (2)	H101···H2^xi	3.427
N11···Br1^iii	3.521 (2)	H101···H5	3.267
N11···O1	3.442 (3)	H101···H6^v	3.130
N11···C9^vi	3.477 (4)	H101···H7^v	3.286
N12···O1	2.805 (3)	H101···H8^vi	2.953
N12···C8^vi	3.552 (4)	H101···H9^vi	3.091
C1···O1	3.515 (3)	H101···H112	2.386
C1···C4^vi	3.580 (4)	H101···H121	2.305
C1···C9^vi	3.535 (4)	H5···O1	2.654
C4···C1^vii	3.580 (4)	H5···C6^v	3.546
C5···O1	3.458 (4)	H5···C7^vi	3.235
C6···O1^v	3.521 (5)	H5···C8^vi	3.211
C8···O1^vii	3.572 (4)	H5···H102	3.152
C8···N12^vii	3.552 (4)	H5···H101	3.267
C8···C8^viii	3.554 (5)	H5···H6^v	2.652
C8···C9^viii	3.419 (5)	H5···H7^vi	3.030
C9···N11^vii	3.477 (4)	H5···H8^vi	2.973
C9···C1^vii	3.535 (4)	H6···O1^v	2.806
C9···C8^viii	3.419 (5)	H6···C5^v	3.403
Br1···H102^ii	2.564	H6···C8^ix	3.350
Br1···H102^iii	3.559	H6···H102^v	3.200
Br1···H2^i	3.214	H6···H101^v	3.130
Br1···H101^iii	2.522	H6···H5^v	2.652
Br1···H9^iv	3.113	H6···H6^v	3.131
Br1···H111	2.501	H6···H8^ix	2.500
Br1···H112^iii	2.761	H7···O1^v	3.500
Se1···H102^ii	3.380	H7···C5^vii	3.339
Se1···H102^vi	3.413	H7···H2^viii	2.936
Se1···H112^ii	3.273	H7···H101^v	3.286
O1···H5	2.654	H7···H5^vii	3.030
O1···H6^v	2.806	H7···H8^ix	3.051
O1···H7^v	3.500	H7···H9^viii	3.501
O1···H8^vi	3.097	H8···O1^vii	3.097
O1···H112	2.814	H8···C4^viii	3.493
O1···H121	1.966	H8···C6^x	3.114
N11···H2^iv	3.559	H8···C7^x	3.385
N11···H101	3.114	H8···C9^viii	3.495
N11···H9^vi	3.287	H8···H101^vii	2.953
N11···H111^iii	3.180	H8···H5^vii	2.973
N11···H112^iii	3.586	H8···H6^x	2.500
N12···H102	3.309	H8···H7^x	3.051
N12···H101	3.044	H8···H121^vii	3.361
C1···H101	3.461	H9···Br1^ii	3.113
C2···H111^ii	3.567	H9···N11^vii	3.287
C2···H112^ii	3.466	H9···C7^viii	3.417
C3···H111^vii	3.587	H9···C8^viii	3.577
C4···H8^viii	3.493	H9···H101^vii	3.091
C5···H6^v	3.403	H9···H7^viii	3.501
C5···H7^vi	3.339	H9···H112^vii	3.053
C6···H5^v	3.546	H111···Br1	2.501
C6···H8^ix	3.114	H111···N11^iii	3.180
C7···H2^viii	3.472	H111···C2^iv	3.567
C7···H5^vii	3.235	H111···C3^vi	3.587
C7···H8^ix	3.385	H111···H102^ii	3.535
C7···H9^viii	3.417	H111···H2^iv	3.330
C8···H101^vii	3.392	H111···H111^iii	2.816
C8···H5^vii	3.211	H111···H112^iii	2.907
C8···H6^x	3.350	H112···Br1^iii	2.761
C8···H9^viii	3.577	H112···Se1^iv	3.273
C8···H121^vii	3.348	H112···O1	2.814
C9···H101^vii	3.464	H112···N11^iii	3.586
C9···H8^viii	3.495	H112···C2^iv	3.466
C9···H112^vii	3.408	H112···C9^vi	3.408
C9···H121^vii	3.554	H112···H102	3.188
H102···Br1^iv	2.564	H112···H2^iv	3.578
H102···Br1^iii	3.559	H112···H101	2.386
H102···Se1^iv	3.380	H112···H9^vi	3.053
H102···Se1^vii	3.413	H112···H111^iii	2.907
H102···N12	3.309	H121···O1	1.966
H102···H2^xi	3.557	H121···C8^vi	3.348
H102···H5	3.152	H121···C9^vi	3.554
H102···H6^v	3.200	H121···H102	2.484
H102···H111^iv	3.535	H121···H101	2.305
H102···H112	3.188	H121···H8^vi	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)

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···Br1^iii	0.86	2.76	3.521 (3)	148
O1—H101···Br1^iii	0.85	2.52	3.342 (2)	164
O1—H102···Br1^iv	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.