Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C14H15ClN2OS, was prepared from a condensation reaction between 2-(4-chloro­phen­yl)-3-methyl­butanoyl chloride and 2-amino­thia­zole. The angle between the thia­zole and benzene rings is 58.87 (8)°. There are N—H...N hydrogen-bonding inter­actions which give rise to dimers in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604013X/rn2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604013X/rn2012Isup2.hkl
Contains datablock I

CCDC reference: 628050

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.098
  • Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT734_ALERT_1_B Contact Calc 3.525(2), Rep 3.5251(4) ...... 5.00 su-Ra S1 -S1 1.555 2.654
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.00 su PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 2 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 0 ALERT type 5 Informative message, check

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: SIR97 (Altomare et al., 1993); 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-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide top
Crystal data top
C14H15ClN2OSF(000) = 1232.00
Mr = 294.80Dx = 1.321 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 10387 reflections
a = 14.925 (6) Åθ = 3.2–27.5°
b = 17.712 (10) ŵ = 0.39 mm1
c = 11.214 (4) ÅT = 298 K
β = 91.497 (14)°Needle, colourless
V = 2963 (2) Å30.39 × 0.32 × 0.28 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2063 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.031
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.863, Tmax = 0.896k = 2222
14487 measured reflectionsl = 1413
3382 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0004Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.098Δρmax = 0.27 e Å3
S = 1.01Δρmin = 0.30 e Å3
3382 reflectionsExtinction correction: Larson (1970), eq. 22
173 parametersExtinction coefficient: 62 (17)
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
xyzUiso*/Ueq
Cl10.02854 (4)0.18695 (4)0.07038 (6)0.1057 (2)
S10.49072 (3)0.10968 (3)0.09363 (3)0.06327 (15)
O10.31766 (6)0.09566 (8)0.03684 (9)0.0671 (4)
N10.56881 (8)0.10153 (9)0.11245 (11)0.0552 (4)
N20.41237 (8)0.09527 (8)0.12263 (10)0.0499 (4)
C10.63402 (11)0.10903 (12)0.02852 (14)0.0662 (5)
C20.60501 (11)0.11407 (12)0.08444 (14)0.0691 (6)
C30.49024 (10)0.10126 (10)0.05887 (12)0.0460 (4)
C40.32915 (10)0.09375 (10)0.07116 (12)0.0506 (4)
C50.25170 (10)0.09162 (10)0.15649 (12)0.0497 (4)
C60.19969 (11)0.16629 (11)0.14601 (14)0.0568 (5)
C70.26035 (13)0.23379 (12)0.17026 (18)0.0784 (7)
C80.12099 (12)0.16759 (12)0.22941 (19)0.0812 (7)
C90.19540 (9)0.02216 (10)0.13468 (12)0.0473 (4)
C100.19315 (11)0.03496 (12)0.21785 (13)0.0578 (5)
C110.14208 (12)0.09857 (12)0.19990 (17)0.0686 (6)
C120.09282 (12)0.10628 (12)0.09502 (18)0.0645 (6)
C130.09383 (12)0.05083 (12)0.01060 (16)0.0631 (6)
C140.14415 (10)0.01307 (11)0.03022 (13)0.0552 (5)
H10.69470.11050.04950.079*
H20.64190.11930.14950.083*
H50.27720.08840.23780.060*
H60.17580.17050.06400.068*
H100.22720.03030.28810.069*
H110.14070.13610.25790.082*
H130.06050.05630.06010.076*
H140.14400.05090.02730.066*
H710.30970.23250.11710.094*
H720.28270.23200.25130.094*
H730.22700.27960.15770.094*
H810.08630.21250.21530.097*
H820.14300.16710.31060.097*
H830.08400.12400.21490.097*
H2010.41700.09240.19910.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1118 (5)0.0736 (4)0.1320 (5)0.0245 (3)0.0097 (4)0.0192 (3)
S10.0515 (2)0.1014 (4)0.0370 (2)0.0032 (2)0.00220 (18)0.0027 (2)
O10.0457 (6)0.1180 (12)0.0374 (5)0.0056 (6)0.0038 (4)0.0025 (6)
N10.0392 (6)0.0846 (12)0.0415 (6)0.0007 (7)0.0002 (5)0.0016 (6)
N20.0389 (6)0.0762 (11)0.0345 (5)0.0028 (6)0.0008 (5)0.0016 (6)
C10.0371 (8)0.1064 (17)0.0553 (9)0.0030 (9)0.0049 (7)0.0043 (10)
C20.0509 (9)0.1073 (18)0.0498 (9)0.0042 (10)0.0127 (7)0.0059 (10)
C30.0435 (8)0.0564 (11)0.0381 (7)0.0001 (7)0.0009 (6)0.0002 (7)
C40.0417 (8)0.0704 (13)0.0394 (7)0.0031 (8)0.0025 (6)0.0012 (7)
C50.0402 (8)0.0735 (14)0.0352 (7)0.0029 (8)0.0024 (6)0.0019 (7)
C60.0497 (9)0.0674 (14)0.0530 (9)0.0029 (9)0.0003 (7)0.0003 (8)
C70.0824 (13)0.0727 (17)0.0800 (13)0.0085 (11)0.0018 (10)0.0010 (11)
C80.0675 (12)0.0824 (18)0.0946 (14)0.0074 (11)0.0234 (10)0.0067 (12)
C90.0372 (7)0.0654 (12)0.0394 (7)0.0043 (7)0.0020 (6)0.0018 (7)
C100.0546 (10)0.0718 (14)0.0468 (8)0.0074 (9)0.0021 (7)0.0054 (8)
C110.0739 (12)0.0626 (14)0.0696 (11)0.0066 (11)0.0085 (9)0.0121 (10)
C120.0575 (10)0.0614 (14)0.0751 (12)0.0001 (9)0.0078 (9)0.0099 (10)
C130.0550 (10)0.0750 (16)0.0591 (10)0.0001 (10)0.0051 (8)0.0107 (10)
C140.0487 (8)0.0707 (14)0.0459 (8)0.0007 (9)0.0045 (7)0.0041 (8)
Geometric parameters (Å, º) top
Cl1—C121.739 (2)C12—C131.364 (2)
S1—C21.7079 (17)C13—C141.373 (2)
S1—C31.7168 (15)N2—H2010.860
O1—C41.2192 (17)C1—H10.930
N1—C11.378 (2)C2—H20.930
N1—C31.3036 (18)C5—H50.980
N2—C31.3844 (19)C6—H60.980
N2—C41.3561 (18)C7—H710.960
C1—C21.331 (2)C7—H720.960
C4—C51.520 (2)C7—H730.960
C5—C61.536 (2)C8—H810.960
C5—C91.506 (2)C8—H820.960
C6—C71.520 (2)C8—H830.960
C6—C81.521 (2)C10—H100.930
C9—C101.377 (2)C11—H110.930
C9—C141.392 (2)C13—H130.930
C10—C111.372 (2)C14—H140.930
C11—C121.377 (2)
S1···S1i3.5251 (4)H10···O1vi2.623
O1···C7ii3.554 (2)H10···C13vi3.537
O1···C10iii3.4510 (19)H10···C14vi3.029
N1···N2iv2.9788 (16)H10···H1iv3.283
N2···N1iv2.9788 (16)H10···H2x2.979
C7···O1ii3.554 (2)H10···H13vi3.415
C7···C11v3.598 (3)H10···H14vi2.469
C10···O1vi3.4510 (19)H10···H73vii3.487
C11···C7vii3.598 (3)H11···Cl1ix3.340
C13···C13viii3.333 (2)H11···O1vi3.531
Cl1···H6viii3.379H11···C7vii2.843
Cl1···H11ix3.340H11···H2x3.506
Cl1···H14viii3.550H11···H6vi3.513
Cl1···H82iii3.433H11···H14vi2.841
S1···H2i3.457H11···H71vii2.807
O1···H10iii2.623H11···H72vii2.605
O1···H11iii3.531H11···H73vii2.633
O1···H73ii2.668H13···C8iii3.222
N1···H5iv2.821H13···C13viii3.046
N1···H72iv3.523H13···C14viii3.175
N1···H201iv2.125H13···H10iii3.415
N2···H201iv3.196H13···H13viii3.030
C1···H5iv2.929H13···H14viii3.231
C1···H72iv3.496H13···H82iii2.749
C1···H201iv3.181H13···H83viii2.985
C3···H201iv3.018H13···H83iii2.824
C4···H73ii3.494H14···Cl1viii3.550
C5···H1iv3.388H14···C10iii2.983
C6···H71ii3.453H14···C11iii3.173
C7···H6ii3.288H14···C13viii3.559
C7···H11v2.843H14···H10iii2.469
C7···H71ii3.415H14···H11iii2.841
C8···H13vi3.222H14···H13viii3.231
C8···H81ix3.269H71···C6ii3.453
C8···H83ix3.232H71···C7ii3.415
C9···H1x3.557H71···H6ii2.674
C9···H2x3.489H71···H11v2.807
C10···H2x2.996H71···H71ii3.197
C10···H14vi2.983H71···H73ii3.123
C11···H2x3.308H72···N1iv3.523
C11···H14vi3.173H72···C1iv3.496
C11···H72vii3.246H72···C11v3.246
C11···H73vii3.297H72···H1iv3.113
C12···H82iii3.466H72···H2xii3.566
C13···H1x3.413H72···H11v2.605
C13···H10iii3.537H73···O1ii2.668
C13···H13viii3.046H73···C4ii3.494
C13···H14viii3.559H73···C11v3.297
C13···H82iii3.145H73···H2xii3.105
C13···H83iii3.560H73···H6ii3.043
C14···H1x3.389H73···H10v3.487
C14···H10iii3.029H73···H11v2.633
C14···H13viii3.175H73···H71ii3.123
H1···C5iv3.388H81···C8ix3.269
H1···C9x3.557H81···H2xii3.435
H1···C13x3.413H81···H81ix2.710
H1···C14x3.389H81···H82ix3.520
H1···H5iv2.442H81···H83ix3.104
H1···H10iv3.283H82···Cl1vi3.433
H1···H72iv3.113H82···C12vi3.466
H1···H82iv3.023H82···C13vi3.145
H1···H201iv3.328H82···H1iv3.023
H2···S1i3.457H82···H13vi2.749
H2···C9x3.489H82···H81ix3.520
H2···C10x2.996H82···H83ix3.477
H2···C11x3.308H83···C8ix3.232
H2···H10x2.979H83···C13vi3.560
H2···H11x3.506H83···H13viii2.985
H2···H72xi3.566H83···H13vi2.824
H2···H73xi3.105H83···H81ix3.104
H2···H81xi3.435H83···H82ix3.477
H5···N1iv2.821H83···H83ix2.648
H5···C1iv2.929H201···N1iv2.125
H5···H1iv2.442H201···N2iv3.196
H6···Cl1viii3.379H201···C1iv3.181
H6···C7ii3.288H201···C3iv3.018
H6···H11iii3.513H201···H1iv3.328
H6···H71ii2.674H201···H201iv2.700
H6···H73ii3.043
C2—S1—C388.51 (7)C2—C1—H1122.0
C1—N1—C3109.18 (12)S1—C2—H2124.6
C3—N2—C4123.61 (11)C1—C2—H2124.6
N1—C1—C2116.01 (14)C4—C5—H5107.7
S1—C2—C1110.73 (12)C6—C5—H5107.7
S1—C3—N1115.57 (11)C9—C5—H5107.7
S1—C3—N2123.13 (10)C5—C6—H6107.9
N1—C3—N2121.29 (13)C7—C6—H6107.9
O1—C4—N2121.72 (13)C8—C6—H6107.9
O1—C4—C5122.44 (13)C6—C7—H71109.5
N2—C4—C5115.82 (12)C6—C7—H72109.5
C4—C5—C6108.75 (13)C6—C7—H73109.5
C4—C5—C9110.38 (13)H71—C7—H72109.5
C6—C5—C9114.33 (12)H71—C7—H73109.5
C5—C6—C7111.47 (14)H72—C7—H73109.5
C5—C6—C8111.27 (15)C6—C8—H81109.5
C7—C6—C8110.13 (16)C6—C8—H82109.5
C5—C9—C10120.90 (13)C6—C8—H83109.5
C5—C9—C14121.55 (14)H81—C8—H82109.5
C10—C9—C14117.55 (15)H81—C8—H83109.5
C9—C10—C11121.81 (15)H82—C8—H83109.5
C10—C11—C12119.26 (18)C9—C10—H10119.1
Cl1—C12—C11119.81 (16)C11—C10—H10119.1
Cl1—C12—C13119.81 (15)C10—C11—H11120.4
C11—C12—C13120.38 (18)C12—C11—H11120.4
C12—C13—C14119.87 (16)C12—C13—H13120.1
C9—C14—C13121.11 (16)C14—C13—H13120.1
C3—N2—H201118.2C9—C14—H14119.4
C4—N2—H201118.2C13—C14—H14119.4
N1—C1—H1122.0
C2—S1—C3—N10.12 (15)C4—C5—C9—C10111.76 (16)
C2—S1—C3—N2179.25 (16)C4—C5—C9—C1468.03 (18)
C3—S1—C2—C10.05 (14)C6—C5—C9—C10125.27 (16)
C1—N1—C3—S10.2 (2)C6—C5—C9—C1454.95 (19)
C1—N1—C3—N2179.23 (16)C9—C5—C6—C7179.44 (13)
C3—N1—C1—C20.1 (2)C9—C5—C6—C856.07 (18)
C3—N2—C4—O11.9 (2)C5—C9—C10—C11179.77 (16)
C3—N2—C4—C5176.51 (15)C5—C9—C14—C13179.27 (15)
C4—N2—C3—S11.5 (2)C10—C9—C14—C130.5 (2)
C4—N2—C3—N1179.13 (16)C14—C9—C10—C110.4 (2)
N1—C1—C2—S10.0 (2)C9—C10—C11—C121.1 (2)
O1—C4—C5—C665.6 (2)C10—C11—C12—Cl1179.43 (14)
O1—C4—C5—C960.6 (2)C10—C11—C12—C130.9 (2)
N2—C4—C5—C6112.83 (15)Cl1—C12—C13—C14179.64 (14)
N2—C4—C5—C9120.99 (15)C11—C12—C13—C140.0 (2)
C4—C5—C6—C756.71 (17)C12—C13—C14—C90.8 (2)
C4—C5—C6—C8179.93 (13)
Symmetry codes: (i) x+1, y, z1/2; (ii) x+1/2, y+1/2, z; (iii) x, y, z1/2; (iv) x+1, y, z+1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x, y, z+1/2; (vii) x+1/2, y1/2, z+1/2; (viii) x, y, z; (ix) x, y, z+1/2; (x) x+1, y, z; (xi) x+1/2, y+1/2, z1/2; (xii) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H201···N1iv0.862.132.9788 (16)172
Symmetry code: (iv) x+1, y, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds