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In the title compound, C9H12N2OS2, the thia­zepane ring adopts a chair conformation. The mol­ecules are linked into chains via N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017223/ob2015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017223/ob2015Isup2.hkl
Contains datablock I

CCDC reference: 610858

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.069
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



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 27.48 From the CIF: _reflns_number_total 2442 Count of symmetry unique reflns 1435 Completeness (_total/calc) 170.17% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1007 Fraction of Friedel pairs measured 0.702 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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.

(+)-6-Amino-2-(2-thienyl)-1,4-thiazepan-5-one top
Crystal data top
C9H12N2OS2F(000) = 480.00
Mr = 228.33Dx = 1.420 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 10137 reflections
a = 6.314 (3) Åθ = 3.1–27.5°
b = 9.785 (3) ŵ = 0.47 mm1
c = 17.289 (6) ÅT = 298 K
V = 1068.2 (7) Å3Chunk, colorless
Z = 40.34 × 0.32 × 0.26 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2239 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.022
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.859, Tmax = 0.886k = 1212
10534 measured reflectionsl = 2222
2442 independent reflections
Refinement top
Refinement on F2(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.025Δρmax = 0.31 e Å3
wR(F2) = 0.069Δρmin = 0.26 e Å3
S = 1.04Extinction correction: Larson (1970)
2442 reflectionsExtinction coefficient: 45 (5)
129 parametersAbsolute structure: Flack (1983), 1008 Friedel pairs
H-atom parameters constrainedAbsolute structure parameter: 0.006 (7)
w = 1/[0.0004Fo2 + 1σ(Fo2)]/(4Fo2)
Special details top

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
xyzUiso*/Ueq
S10.04353 (6)0.60974 (4)0.20201 (2)0.03931 (9)
S20.17570 (6)0.89377 (5)0.09627 (3)0.04656 (11)
O10.0031 (2)0.22126 (11)0.04547 (6)0.0516 (3)
N10.1586 (2)0.42420 (12)0.03804 (8)0.0433 (3)
N20.3508 (2)0.32026 (17)0.12712 (10)0.0599 (5)
C10.2521 (2)0.61538 (16)0.12898 (9)0.0371 (3)
C20.1774 (3)0.57177 (16)0.04817 (9)0.0409 (4)
C30.0011 (2)0.34424 (14)0.06290 (9)0.0384 (4)
C40.1661 (2)0.40696 (16)0.11468 (9)0.0393 (3)
C50.0670 (3)0.44160 (17)0.19316 (9)0.0439 (4)
C60.3292 (2)0.76025 (14)0.13013 (9)0.0370 (3)
C70.5146 (3)0.80840 (19)0.15989 (11)0.0508 (5)
C80.5304 (3)0.9526 (2)0.15511 (12)0.0587 (5)
C90.3609 (3)1.01199 (18)0.12234 (11)0.0507 (5)
H10.36790.55520.14520.045*
H40.21410.49230.09080.047*
H70.61920.75280.18100.061*
H80.64691.00140.17290.070*
H90.34641.10560.11480.061*
H210.03970.61250.03880.049*
H220.27810.60600.01050.049*
H510.17610.43190.23230.053*
H520.04520.37620.20290.053*
H1010.25970.38440.01340.052*
H2010.39760.29340.08290.072*
H2020.28580.24740.14380.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0512 (2)0.03343 (18)0.03329 (18)0.00322 (19)0.00151 (17)0.00658 (16)
S20.0472 (2)0.0392 (2)0.0534 (2)0.0026 (2)0.0086 (2)0.0038 (2)
O10.0605 (8)0.0345 (5)0.0599 (7)0.0002 (5)0.0073 (6)0.0151 (5)
N10.0463 (7)0.0381 (7)0.0456 (7)0.0005 (6)0.0090 (6)0.0152 (5)
N20.0593 (10)0.0604 (9)0.0599 (10)0.0217 (8)0.0038 (8)0.0111 (8)
C10.0353 (7)0.0330 (6)0.0430 (8)0.0026 (6)0.0013 (6)0.0044 (7)
C20.0496 (9)0.0372 (7)0.0359 (8)0.0052 (7)0.0076 (7)0.0060 (6)
C30.0451 (9)0.0348 (7)0.0352 (7)0.0021 (6)0.0107 (6)0.0064 (5)
C40.0442 (8)0.0369 (7)0.0368 (7)0.0042 (7)0.0008 (6)0.0033 (6)
C50.0605 (10)0.0374 (7)0.0338 (8)0.0088 (7)0.0009 (8)0.0001 (6)
C60.0369 (8)0.0356 (7)0.0387 (8)0.0000 (6)0.0006 (7)0.0026 (6)
C70.0445 (10)0.0475 (9)0.0603 (11)0.0048 (8)0.0072 (8)0.0006 (8)
C80.0525 (11)0.0542 (10)0.0693 (12)0.0181 (9)0.0073 (10)0.0054 (9)
C90.0599 (12)0.0382 (8)0.0540 (10)0.0131 (8)0.0034 (9)0.0018 (8)
Geometric parameters (Å, º) top
S1—C11.8254 (15)C8—C91.343 (3)
S1—C51.7938 (17)N1—H1010.860
S2—C61.7291 (16)N2—H2010.861
S2—C91.705 (2)N2—H2020.872
O1—C31.2408 (18)C1—H10.980
N1—C21.459 (2)C2—H210.970
N1—C31.336 (2)C2—H220.970
N2—C41.458 (2)C4—H40.980
C1—C21.535 (2)C5—H510.970
C1—C61.499 (2)C5—H520.970
C3—C41.514 (2)C7—H70.930
C4—C51.532 (2)C8—H80.930
C6—C71.363 (2)C9—H90.930
C7—C81.417 (2)
S2···O1i3.5092 (12)H8···H1xiii3.189
O1···S2ii3.5092 (12)H8···H22vii3.442
O1···O1iii3.5716 (19)H8···H51xi3.462
O1···O1iv3.5716 (19)H8···H52xiii3.144
O1···N1iii2.9450 (19)H8···H101vii3.484
O1···N2iv3.161 (2)H8···H201viii3.266
O1···C9ii3.353 (2)H8···H202viii2.496
N1···O1iv2.9450 (19)H9···O1i2.755
N1···C9v3.408 (2)H9···O1vii3.384
N2···O1iii3.161 (2)H9···N1i3.589
N2···C9vi3.524 (2)H9···N1vii3.310
C9···O1i3.353 (2)H9···N2viii2.848
C9···N1vii3.408 (2)H9···C3i3.318
C9···N2viii3.524 (2)H9···C3vii3.262
S1···H7ix3.045H9···H51xi3.321
S1···H8x3.101H9···H52i3.597
S1···H51xi3.454H9···H101i3.289
S1···H52xi3.132H9···H101vii3.426
S1···H202xi3.356H9···H201viii2.509
S2···H4vii3.490H9···H202viii2.751
S2···H21vii3.277H21···S2v3.277
S2···H22v3.116H21···C6v3.441
S2···H51xi2.987H21···C7v3.524
O1···H9ii2.755H21···C8v3.412
O1···H9v3.384H21···C9v3.243
O1···H101iii2.086H21···H22v3.323
O1···H201iv2.321H22···S2vii3.116
O1···H202iv3.562H22···C7v3.485
N1···H9ii3.589H22···C8v3.312
N1···H9v3.310H22···H8v3.442
N1···H201xii3.177H22···H21vii3.323
N1···H201iv3.005H51···S1xiv3.454
N1···H202iv3.582H51···S2xiv2.987
N2···H1ix2.921H51···C6xiv3.068
N2···H8vi3.219H51···C7xiv3.083
N2···H9vi2.848H51···C8xiv2.972
N2···H101ix3.210H51···C9xiv2.880
N2···H101iii3.226H51···H1ix3.466
C3···H9ii3.318H51···H7ix3.509
C3···H9v3.262H51···H8xiv3.462
C3···H101iii3.012H51···H9xiv3.321
C3···H201iv2.928H52···S1xiv3.132
C4···H1ix3.322H52···H7x3.159
C5···H8x3.569H52···H8x3.144
C6···H21vii3.441H52···H9ii3.597
C6···H51xi3.068H101···O1iv2.086
C7···H21vii3.524H101···N2xii3.210
C7···H22vii3.485H101···N2iv3.226
C7···H51xi3.083H101···C3iv3.012
C8···H21vii3.412H101···C9v3.589
C8···H22vii3.312H101···H8v3.484
C8···H51xi2.972H101···H9ii3.289
C8···H201viii3.590H101···H9v3.426
C8···H202viii3.116H101···H201xii2.630
C9···H21vii3.243H101···H201iv2.606
C9···H51xi2.880H101···H202iv3.023
C9···H101vii3.589H201···O1iii2.321
C9···H201viii3.221H201···N1ix3.177
C9···H202viii3.228H201···N1iii3.005
H1···N2xii2.921H201···C3iii2.928
H1···C4xii3.322H201···C8vi3.590
H1···H4xii2.869H201···C9vi3.221
H1···H8x3.189H201···H1ix3.148
H1···H51xii3.466H201···H8vi3.266
H1···H201xii3.148H201···H9vi2.509
H4···S2v3.490H201···H101ix2.630
H4···H1ix2.869H201···H101iii2.606
H4···H7ix3.168H202···S1xiv3.356
H7···S1xii3.045H202···O1iii3.562
H7···H4xii3.168H202···N1iii3.582
H7···H51xii3.509H202···C8vi3.116
H7···H52xiii3.159H202···C9vi3.228
H8···S1xiii3.101H202···H8vi2.496
H8···N2viii3.219H202···H9vi2.751
H8···C5xiii3.569H202···H101iii3.023
C1—S1—C5104.45 (7)H201—N2—H202101.9
C6—S2—C992.21 (8)S1—C1—H1108.8
C2—N1—C3126.95 (14)C2—C1—H1108.8
S1—C1—C2113.54 (11)C6—C1—H1108.8
S1—C1—C6104.71 (10)N1—C2—H21108.3
C2—C1—C6112.01 (12)N1—C2—H22108.3
N1—C2—C1114.15 (12)C1—C2—H21108.3
O1—C3—N1120.37 (15)C1—C2—H22108.3
O1—C3—C4121.45 (14)H21—C2—H22109.5
N1—C3—C4118.15 (13)N2—C4—H4108.1
N2—C4—C3114.15 (13)C3—C4—H4108.1
N2—C4—C5108.95 (13)C5—C4—H4108.1
C3—C4—C5109.17 (14)S1—C5—H51107.8
S1—C5—C4115.94 (11)S1—C5—H52107.8
S2—C6—C1121.86 (12)C4—C5—H51107.8
S2—C6—C7110.38 (12)C4—C5—H52107.8
C1—C6—C7127.67 (15)H51—C5—H52109.5
C6—C7—C8112.50 (17)C6—C7—H7123.8
C7—C8—C9113.55 (19)C8—C7—H7123.8
S2—C9—C8111.36 (14)C7—C8—H8123.2
C2—N1—H101116.5C9—C8—H8123.2
C3—N1—H101116.5S2—C9—H9124.3
C4—N2—H201108.7C8—C9—H9124.3
C4—N2—H20298.5
C1—S1—C5—C461.14 (14)C2—C1—C6—C7130.31 (18)
C5—S1—C1—C251.57 (12)C6—C1—C2—N1163.30 (14)
C5—S1—C1—C6174.04 (10)O1—C3—C4—N212.8 (2)
C6—S2—C9—C80.03 (12)O1—C3—C4—C5109.35 (17)
C9—S2—C6—C1176.74 (14)N1—C3—C4—N2169.19 (14)
C9—S2—C6—C70.03 (11)N1—C3—C4—C568.62 (18)
C2—N1—C3—O1174.70 (15)N2—C4—C5—S1144.26 (12)
C2—N1—C3—C47.3 (2)C3—C4—C5—S190.48 (14)
C3—N1—C2—C178.4 (2)S2—C6—C7—C80.09 (16)
S1—C1—C2—N178.35 (16)C1—C6—C7—C8176.45 (16)
S1—C1—C6—S269.96 (13)C6—C7—C8—C90.1 (2)
S1—C1—C6—C7106.22 (17)C7—C8—C9—S20.1 (2)
C2—C1—C6—S253.51 (18)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x1/2, y+1/2, z; (iv) x+1/2, y+1/2, z; (v) x1/2, y+3/2, z; (vi) x1, y1, z; (vii) x+1/2, y+3/2, z; (viii) x+1, y+1, z; (ix) x1, y, z; (x) x+1, y1/2, z+1/2; (xi) x, y+1/2, z+1/2; (xii) x+1, y, z; (xiii) x+1, y+1/2, z+1/2; (xiv) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O1iv0.862.092.945 (2)177
N2—H201···O1iii0.862.323.161 (2)165
N2—H202···O10.872.482.784 (2)101
Symmetry codes: (iii) x1/2, y+1/2, z; (iv) x+1/2, y+1/2, z.
 

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