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The title compound, C13H13BrN4OS, crystallizes with two molecules in the asymmetric unit. Inter­molecular O—H...N hydrogen bonds enhance the stability of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006775/fl2001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006775/fl2001Isup2.hkl
Contains datablock I

CCDC reference: 605063

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.080
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. Br2 .. 3.47 Ang.
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 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

3-[6-(4-Bromophenyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-3-yl]propanol top
Crystal data top
C13H13BrN4OSF(000) = 1424
Mr = 353.24Dx = 1.693 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5420 reflections
a = 6.9002 (4) Åθ = 2.6–25.0°
b = 15.740 (1) ŵ = 3.12 mm1
c = 25.533 (1) ÅT = 298 K
β = 91.132 (1)°Block, colorless
V = 2772.6 (3) Å30.43 × 0.26 × 0.18 mm
Z = 8
Data collection top
Bruker SMART APEX area-detector
diffractometer
4895 independent reflections
Radiation source: fine-focus sealed tube3926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 85
Tmin = 0.392, Tmax = 0.579k = 1818
14310 measured reflectionsl = 2630
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.4483P]
where P = (Fo2 + 2Fc2)/3
4895 reflections(Δ/σ)max = 0.002
361 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

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
Br11.50890 (4)0.28876 (2)0.596326 (11)0.05903 (11)
S10.64139 (11)0.14213 (4)0.37010 (3)0.04813 (19)
O10.0772 (3)0.53540 (11)0.37853 (7)0.0460 (5)
H10.00930.52290.35740.055*
N10.7215 (3)0.31055 (11)0.43248 (7)0.0308 (4)
N20.5782 (3)0.30618 (11)0.39381 (7)0.0308 (4)
N30.3680 (3)0.25711 (13)0.33567 (8)0.0424 (5)
N40.3227 (3)0.34231 (13)0.34673 (8)0.0432 (5)
C11.3067 (4)0.27533 (15)0.54575 (9)0.0365 (6)
C21.3402 (4)0.23019 (15)0.50080 (9)0.0381 (6)
H2A1.46090.20580.49540.046*
C31.1923 (3)0.22131 (15)0.46346 (9)0.0357 (6)
H31.21390.19000.43320.043*
C41.0121 (3)0.25882 (14)0.47084 (8)0.0313 (5)
C50.9823 (4)0.30376 (15)0.51711 (10)0.0394 (6)
H50.86230.32860.52280.047*
C61.1286 (4)0.31188 (16)0.55461 (10)0.0417 (6)
H61.10710.34160.58540.050*
C70.8585 (3)0.25463 (14)0.42970 (8)0.0315 (5)
C80.8732 (4)0.19072 (17)0.38589 (10)0.0473 (7)
H8A0.96510.14680.39610.057*
H8B0.92180.21880.35500.057*
C90.5201 (3)0.23848 (15)0.36398 (9)0.0339 (5)
C100.4470 (3)0.36994 (15)0.38199 (9)0.0346 (5)
C110.4541 (4)0.45633 (15)0.40593 (10)0.0386 (6)
H11A0.44870.49840.37820.046*
H11B0.57700.46310.42460.046*
C120.2898 (4)0.47347 (16)0.44376 (10)0.0438 (6)
H12A0.29520.43120.47140.053*
H12B0.31080.52860.45990.053*
C130.0887 (4)0.47214 (16)0.41860 (10)0.0450 (6)
H13A0.06280.41660.40360.054*
H13B0.00770.48340.44490.054*
Br20.30284 (5)0.45433 (2)0.032491 (13)0.06817 (13)
S20.50804 (9)0.57294 (4)0.27302 (2)0.03894 (16)
O21.0874 (3)0.17957 (10)0.26086 (7)0.0468 (5)
H21.17010.19100.28330.056*
N50.4457 (3)0.40734 (11)0.20786 (7)0.0293 (4)
N60.5878 (3)0.41158 (11)0.24717 (7)0.0276 (4)
N70.7936 (3)0.46127 (12)0.30606 (8)0.0383 (5)
N80.8450 (3)0.37709 (12)0.29371 (8)0.0396 (5)
C140.1185 (4)0.45448 (15)0.08881 (10)0.0386 (6)
C150.0611 (4)0.41939 (17)0.08118 (10)0.0449 (6)
H150.09040.39480.04920.054*
C160.1975 (4)0.42095 (15)0.12138 (9)0.0399 (6)
H160.31900.39700.11640.048*
C170.1554 (3)0.45804 (13)0.16949 (9)0.0288 (5)
C180.0281 (3)0.49339 (15)0.17593 (9)0.0343 (5)
H180.05850.51890.20760.041*
C190.1658 (3)0.49087 (16)0.13555 (10)0.0405 (6)
H190.28860.51360.14020.049*
C200.3034 (3)0.45970 (13)0.21243 (8)0.0268 (5)
C210.2803 (3)0.51823 (15)0.25823 (9)0.0343 (5)
H21A0.24120.48580.28860.041*
H21B0.17990.55960.25030.041*
C220.6402 (3)0.47941 (14)0.27781 (9)0.0306 (5)
C230.7222 (3)0.34947 (14)0.25845 (9)0.0321 (5)
C240.7190 (3)0.26343 (14)0.23382 (10)0.0352 (6)
H24A0.59640.25630.21510.042*
H24B0.72490.22100.26140.042*
C250.8831 (4)0.24647 (15)0.19594 (9)0.0385 (6)
H25A0.86030.19230.17880.046*
H25B0.88110.29010.16910.046*
C261.0817 (4)0.24503 (16)0.22223 (10)0.0415 (6)
H26A1.18000.23460.19630.050*
H26B1.10830.29950.23860.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05215 (19)0.0779 (2)0.04632 (18)0.00937 (15)0.01754 (14)0.00066 (14)
S10.0522 (4)0.0367 (3)0.0549 (4)0.0084 (3)0.0124 (3)0.0121 (3)
O10.0438 (11)0.0456 (10)0.0481 (11)0.0044 (8)0.0116 (9)0.0037 (8)
N10.0280 (10)0.0327 (10)0.0317 (10)0.0014 (9)0.0019 (8)0.0000 (8)
N20.0289 (10)0.0321 (10)0.0314 (10)0.0027 (9)0.0028 (8)0.0011 (8)
N30.0390 (12)0.0466 (12)0.0412 (12)0.0035 (10)0.0067 (10)0.0081 (10)
N40.0387 (12)0.0450 (12)0.0455 (12)0.0085 (10)0.0104 (10)0.0056 (10)
C10.0382 (14)0.0387 (13)0.0325 (13)0.0049 (11)0.0050 (11)0.0062 (11)
C20.0311 (13)0.0449 (14)0.0383 (14)0.0067 (11)0.0008 (11)0.0051 (11)
C30.0372 (14)0.0401 (13)0.0300 (12)0.0075 (11)0.0035 (11)0.0017 (10)
C40.0349 (13)0.0310 (12)0.0281 (12)0.0012 (10)0.0007 (10)0.0032 (10)
C50.0357 (14)0.0427 (14)0.0398 (14)0.0113 (12)0.0023 (11)0.0032 (11)
C60.0473 (16)0.0443 (14)0.0336 (13)0.0028 (13)0.0007 (12)0.0059 (11)
C70.0310 (13)0.0336 (12)0.0300 (12)0.0003 (11)0.0029 (10)0.0013 (10)
C80.0372 (15)0.0586 (17)0.0456 (15)0.0171 (13)0.0083 (12)0.0155 (13)
C90.0318 (13)0.0382 (13)0.0318 (12)0.0006 (11)0.0016 (10)0.0028 (10)
C100.0319 (13)0.0348 (12)0.0372 (13)0.0061 (11)0.0011 (11)0.0026 (10)
C110.0366 (14)0.0338 (13)0.0451 (15)0.0046 (11)0.0041 (12)0.0024 (11)
C120.0528 (17)0.0402 (14)0.0384 (14)0.0050 (12)0.0014 (12)0.0019 (11)
C130.0436 (16)0.0441 (15)0.0477 (15)0.0020 (12)0.0070 (12)0.0028 (12)
Br20.0623 (2)0.0763 (2)0.0645 (2)0.00097 (17)0.03692 (17)0.00350 (16)
S20.0420 (4)0.0282 (3)0.0462 (4)0.0027 (3)0.0101 (3)0.0073 (3)
O20.0413 (10)0.0411 (10)0.0575 (11)0.0028 (8)0.0133 (9)0.0068 (8)
N50.0277 (10)0.0282 (10)0.0318 (10)0.0011 (8)0.0059 (8)0.0010 (8)
N60.0256 (10)0.0270 (9)0.0302 (10)0.0002 (8)0.0039 (8)0.0014 (8)
N70.0371 (12)0.0391 (11)0.0382 (11)0.0030 (9)0.0082 (9)0.0061 (9)
N80.0381 (12)0.0361 (11)0.0439 (12)0.0051 (9)0.0115 (10)0.0031 (9)
C140.0406 (15)0.0349 (13)0.0397 (14)0.0046 (11)0.0136 (11)0.0074 (11)
C150.0474 (16)0.0503 (15)0.0367 (14)0.0074 (13)0.0075 (12)0.0095 (12)
C160.0353 (14)0.0446 (14)0.0396 (14)0.0106 (12)0.0054 (11)0.0082 (11)
C170.0308 (12)0.0236 (11)0.0320 (12)0.0024 (10)0.0017 (10)0.0029 (9)
C180.0307 (13)0.0381 (13)0.0341 (13)0.0004 (11)0.0023 (10)0.0018 (10)
C190.0272 (13)0.0451 (14)0.0489 (15)0.0026 (11)0.0030 (11)0.0080 (12)
C200.0282 (12)0.0233 (10)0.0289 (11)0.0030 (10)0.0002 (9)0.0030 (9)
C210.0324 (13)0.0366 (13)0.0336 (12)0.0055 (11)0.0037 (10)0.0018 (10)
C220.0322 (13)0.0304 (12)0.0292 (12)0.0022 (10)0.0028 (10)0.0014 (10)
C230.0284 (12)0.0315 (12)0.0363 (13)0.0016 (10)0.0030 (10)0.0032 (10)
C240.0313 (13)0.0274 (11)0.0467 (14)0.0005 (10)0.0072 (11)0.0002 (11)
C250.0448 (15)0.0329 (12)0.0376 (14)0.0026 (12)0.0042 (12)0.0001 (11)
C260.0359 (14)0.0421 (14)0.0466 (15)0.0007 (12)0.0049 (11)0.0009 (12)
Geometric parameters (Å, º) top
Br1—C11.894 (2)Br2—C141.901 (2)
S1—C91.738 (2)S2—C221.735 (2)
S1—C81.811 (3)S2—C211.825 (2)
O1—C131.429 (3)O2—C261.426 (3)
O1—H10.8200O2—H20.8199
N1—C71.295 (3)N5—C201.289 (3)
N1—N21.385 (2)N5—N61.391 (2)
N2—C91.365 (3)N6—C221.368 (3)
N2—C101.381 (3)N6—C231.374 (3)
N3—C91.296 (3)N7—C221.301 (3)
N3—N41.407 (3)N7—N81.409 (3)
N4—C101.306 (3)N8—C231.299 (3)
C1—C21.373 (3)C14—C191.369 (4)
C1—C61.380 (4)C14—C151.374 (4)
C2—C31.390 (3)C15—C161.379 (3)
C2—H2A0.9300C15—H150.9300
C3—C41.393 (3)C16—C171.396 (3)
C3—H30.9300C16—H160.9300
C4—C51.396 (3)C17—C181.396 (3)
C4—C71.479 (3)C17—C201.484 (3)
C5—C61.383 (3)C18—C191.389 (3)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—H190.9300
C7—C81.509 (3)C20—C211.500 (3)
C8—H8A0.9700C21—H21A0.9700
C8—H8B0.9700C21—H21B0.9700
C10—C111.491 (3)C23—C241.493 (3)
C11—C121.528 (4)C24—C251.527 (4)
C11—H11A0.9700C24—H24A0.9700
C11—H11B0.9700C24—H24B0.9700
C12—C131.518 (4)C25—C261.514 (3)
C12—H12A0.9700C25—H25A0.9700
C12—H12B0.9700C25—H25B0.9700
C13—H13A0.9700C26—H26A0.9700
C13—H13B0.9700C26—H26B0.9700
C9—S1—C894.20 (12)C22—S2—C2193.63 (10)
C13—O1—H1109.4C26—O2—H2109.4
C7—N1—N2116.05 (18)C20—N5—N6115.56 (17)
C9—N2—C10105.15 (19)C22—N6—C23105.40 (17)
C9—N2—N1129.34 (18)C22—N6—N5128.67 (17)
C10—N2—N1125.13 (18)C23—N6—N5125.48 (17)
C9—N3—N4106.53 (19)C22—N7—N8106.74 (18)
C10—N4—N3108.06 (19)C23—N8—N7107.82 (18)
C2—C1—C6121.2 (2)C19—C14—C15121.5 (2)
C2—C1—Br1119.56 (19)C19—C14—Br2119.52 (19)
C6—C1—Br1119.23 (19)C15—C14—Br2118.95 (19)
C1—C2—C3119.4 (2)C14—C15—C16119.4 (2)
C1—C2—H2A120.3C14—C15—H15120.3
C3—C2—H2A120.3C16—C15—H15120.3
C2—C3—C4120.7 (2)C15—C16—C17120.7 (2)
C2—C3—H3119.7C15—C16—H16119.6
C4—C3—H3119.7C17—C16—H16119.6
C3—C4—C5118.4 (2)C18—C17—C16118.4 (2)
C3—C4—C7121.0 (2)C18—C17—C20121.3 (2)
C5—C4—C7120.6 (2)C16—C17—C20120.3 (2)
C6—C5—C4121.0 (2)C19—C18—C17120.7 (2)
C6—C5—H5119.5C19—C18—H18119.7
C4—C5—H5119.5C17—C18—H18119.7
C1—C6—C5119.2 (2)C14—C19—C18119.2 (2)
C1—C6—H6120.4C14—C19—H19120.4
C5—C6—H6120.4C18—C19—H19120.4
N1—C7—C4116.40 (19)N5—C20—C17115.88 (19)
N1—C7—C8123.6 (2)N5—C20—C21123.77 (19)
C4—C7—C8119.9 (2)C17—C20—C21120.33 (19)
C7—C8—S1112.00 (18)C20—C21—S2110.32 (16)
C7—C8—H8A109.2C20—C21—H21A109.6
S1—C8—H8A109.2S2—C21—H21A109.6
C7—C8—H8B109.2C20—C21—H21B109.6
S1—C8—H8B109.2S2—C21—H21B109.6
H8A—C8—H8B107.9H21A—C21—H21B108.1
N3—C9—N2111.1 (2)N7—C22—N6110.42 (19)
N3—C9—S1129.12 (19)N7—C22—S2130.25 (17)
N2—C9—S1119.69 (17)N6—C22—S2119.30 (16)
N4—C10—N2109.1 (2)N8—C23—N6109.61 (19)
N4—C10—C11127.0 (2)N8—C23—C24126.8 (2)
N2—C10—C11123.9 (2)N6—C23—C24123.54 (19)
C10—C11—C12113.7 (2)C23—C24—C25114.8 (2)
C10—C11—H11A108.8C23—C24—H24A108.6
C12—C11—H11A108.8C25—C24—H24A108.6
C10—C11—H11B108.8C23—C24—H24B108.6
C12—C11—H11B108.8C25—C24—H24B108.6
H11A—C11—H11B107.7H24A—C24—H24B107.5
C13—C12—C11114.4 (2)C26—C25—C24113.4 (2)
C13—C12—H12A108.6C26—C25—H25A108.9
C11—C12—H12A108.6C24—C25—H25A108.9
C13—C12—H12B108.6C26—C25—H25B108.9
C11—C12—H12B108.6C24—C25—H25B108.9
H12A—C12—H12B107.6H25A—C25—H25B107.7
O1—C13—C12109.3 (2)O2—C26—C25109.2 (2)
O1—C13—H13A109.8O2—C26—H26A109.8
C12—C13—H13A109.8C25—C26—H26A109.8
O1—C13—H13B109.8O2—C26—H26B109.8
C12—C13—H13B109.8C25—C26—H26B109.8
H13A—C13—H13B108.3H26A—C26—H26B108.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N3i0.822.162.956 (3)164
O1—H1···N7ii0.822.112.911 (3)166
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

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