Ethyl 4-tert-butyl-2-(3-phenyl­ureido)-1,3-thia­zole-5-carboxyl­ate

The structure of the title compound, C₁₇H₂₁N₃O₃S, (I), comprises an essentially flat mol­ecule with a dihedral angle of 25.7 (2)° between the thia­zole and phenyl rings. An intramolecular hydrogen bond exists between the phenyl amine and the thia­zole N atom, while intermolecular hydrogen bonds exist to and from the other two components of the urea moiety.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.136
• Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.794

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.98
         From the CIF: _reflns_number_total               2867
         Count of symmetry unique reflns         1793
         Completeness (_total/calc)            159.90%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1074
         Fraction of Friedel pairs measured     0.599
         Are heavy atom types Z>Si present          yes
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Ethyl 4-tert-butyl-2-(3-phenylureido)-1,3-thiazole-5-carboxylate

Crystal data

C17H21N3O3S	Dx = 1.334 Mg m^−3
Mr = 347.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8676 reflections
a = 6.1391 (4) Å	θ = 2.9–27.5°
b = 9.9755 (6) Å	µ = 0.21 mm^−1
c = 28.248 (2) Å	T = 120 K
V = 1729.9 (2) Å^3	Block, colourless
Z = 4	0.10 × 0.07 × 0.06 mm
F(000) = 736

Data collection

Bruker–Nonius KappaCCD area detector diffractometer	2867 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −6→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.980, Tmax = 0.988	l = −33→18
6163 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.79	(Δ/σ)max < 0.001
2867 reflections	Δρmax = 0.26 e Å^−3
229 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Absolute structure: Flack (1983), 706 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.19 (13)

Special details

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.4665 (0.0094) x - 6.2890 (0.0108) y + 15.0459 (0.0543) z = 0.1624 (0.0138)

* -0.0026 (0.0016) S1 * 0.0034 (0.0022) C2 * -0.0026 (0.0017) N3 * 0.0009 (0.0006) C5 * 0.0009 (0.0006) C5

Rms deviation of fitted atoms = 0.0023

2.6057 (0.0088) x - 3.3983 (0.0154) y + 23.6980 (0.0252) z = 2.1328 (0.0264)

Angle to previous plane (with approximate e.s.d.) = 25.67 (0.23)

* 0.0013 (0.0028) C24 * -0.0042 (0.0028) C25 * 0.0045 (0.0028) C26 * -0.0020 (0.0029) C27 * -0.0008 (0.0029) C28 * 0.0011 (0.0028) C29

Rms deviation of fitted atoms = 0.0027

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.03482 (16)	−0.26387 (10)	0.09594 (3)	0.0201 (3)
C2	0.1869 (6)	−0.1605 (4)	0.08846 (14)	0.0192 (9)
N3	0.2119 (5)	−0.0682 (3)	0.12088 (12)	0.0184 (8)
C4	0.0523 (6)	−0.0733 (4)	0.15504 (13)	0.0184 (9)
C5	−0.0972 (6)	−0.1752 (4)	0.14761 (14)	0.0187 (9)
N21	0.3266 (6)	−0.1741 (4)	0.05020 (12)	0.0207 (8)
H21	0.295 (6)	−0.235 (4)	0.0317 (14)	0.013 (11)*
C22	0.5050 (6)	−0.0960 (4)	0.03774 (13)	0.0169 (9)
O22	0.6105 (4)	−0.1253 (3)	0.00222 (9)	0.0217 (7)
N23	0.5454 (6)	0.0100 (3)	0.06644 (12)	0.0199 (8)
H23	0.435 (6)	0.013 (4)	0.0919 (14)	0.020 (10)*
C24	0.7084 (7)	0.1097 (4)	0.06134 (13)	0.0176 (9)
C25	0.9038 (7)	0.0898 (4)	0.03677 (15)	0.0242 (10)
H25	0.9323	0.0069	0.0214	0.030*
C26	1.0545 (7)	0.1924 (4)	0.03529 (14)	0.0239 (10)
H26	1.1882	0.1788	0.0191	0.030*
C27	1.0158 (7)	0.3142 (5)	0.05673 (14)	0.0278 (10)
H27	1.1208	0.3840	0.0550	0.035*
C28	0.8207 (7)	0.3338 (4)	0.08104 (14)	0.0254 (10)
H28	0.7919	0.4170	0.0961	0.032*
C29	0.6703 (7)	0.2320 (4)	0.08305 (14)	0.0247 (10)
H29	0.5376	0.2457	0.0997	0.031*
C41	0.0621 (6)	0.0311 (4)	0.19464 (13)	0.0201 (9)
C42	0.2408 (6)	0.1330 (4)	0.18309 (14)	0.0230 (10)
H421	0.3813	0.0868	0.1807	0.029*
H422	0.2481	0.2004	0.2083	0.029*
H423	0.2075	0.1770	0.1529	0.029*
C43	0.1224 (7)	−0.0389 (5)	0.24145 (14)	0.0259 (10)
H431	0.2629	−0.0844	0.2379	0.032*
H432	0.0099	−0.1048	0.2495	0.032*
H433	0.1327	0.0280	0.2668	0.032*
C44	−0.1527 (7)	0.1061 (4)	0.19972 (16)	0.0256 (11)
H441	−0.1400	0.1728	0.2251	0.032*
H442	−0.2690	0.0425	0.2075	0.032*
H443	−0.1874	0.1514	0.1699	0.032*
C51	−0.2832 (6)	−0.2207 (4)	0.17572 (14)	0.0176 (9)
O51	−0.3433 (4)	−0.1748 (3)	0.21338 (10)	0.0253 (7)
O52	−0.3826 (4)	−0.3260 (3)	0.15494 (10)	0.0240 (7)
C53	−0.5728 (7)	−0.3790 (4)	0.18000 (15)	0.0238 (10)
H531	−0.6964	−0.3156	0.1775	0.030*
H532	−0.5384	−0.3924	0.2139	0.030*
C54	−0.6305 (8)	−0.5105 (5)	0.15721 (18)	0.0387 (13)
H541	−0.5153	−0.5760	0.1636	0.048*
H542	−0.6453	−0.4979	0.1229	0.048*
H543	−0.7686	−0.5432	0.1702	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0218 (6)	0.0207 (6)	0.0179 (5)	−0.0039 (5)	0.0001 (4)	−0.0021 (5)
C2	0.019 (2)	0.018 (2)	0.020 (2)	0.0048 (18)	0.0021 (18)	−0.0006 (19)
N3	0.0176 (19)	0.016 (2)	0.022 (2)	−0.0037 (15)	0.0022 (15)	−0.0015 (15)
C4	0.024 (2)	0.017 (2)	0.014 (2)	−0.0001 (18)	0.0002 (18)	0.0042 (16)
C5	0.020 (2)	0.018 (2)	0.019 (2)	−0.0029 (18)	0.0003 (17)	0.0008 (18)
N21	0.023 (2)	0.020 (2)	0.0192 (19)	−0.0013 (18)	0.0018 (16)	−0.0052 (17)
C22	0.021 (2)	0.016 (2)	0.014 (2)	0.0021 (18)	−0.0010 (18)	0.0029 (16)
O22	0.0234 (16)	0.0240 (16)	0.0178 (15)	0.0020 (12)	0.0018 (12)	−0.0031 (13)
N23	0.0206 (19)	0.0215 (19)	0.0175 (18)	−0.0043 (17)	0.0043 (16)	−0.0022 (15)
C24	0.021 (2)	0.020 (2)	0.012 (2)	−0.0046 (19)	−0.0015 (16)	0.0017 (17)
C25	0.027 (3)	0.027 (3)	0.019 (2)	0.0027 (19)	−0.0006 (18)	0.0029 (18)
C26	0.016 (2)	0.033 (3)	0.023 (2)	−0.003 (2)	−0.0009 (18)	0.0064 (19)
C27	0.029 (3)	0.031 (3)	0.023 (2)	−0.010 (2)	−0.006 (2)	0.0067 (19)
C28	0.029 (3)	0.025 (2)	0.022 (2)	−0.009 (2)	0.001 (2)	−0.0039 (19)
C29	0.026 (2)	0.024 (2)	0.023 (2)	−0.005 (2)	0.0056 (18)	−0.0023 (19)
C41	0.024 (2)	0.020 (2)	0.016 (2)	−0.005 (2)	0.0026 (18)	−0.0004 (17)
C42	0.030 (3)	0.021 (3)	0.018 (2)	−0.003 (2)	0.0020 (18)	−0.0069 (19)
C43	0.029 (2)	0.029 (3)	0.020 (2)	−0.002 (2)	−0.0015 (19)	−0.004 (2)
C44	0.025 (3)	0.027 (3)	0.025 (2)	0.002 (2)	0.005 (2)	−0.003 (2)
C51	0.017 (2)	0.018 (2)	0.017 (2)	0.0044 (18)	−0.0019 (17)	0.0014 (18)
O51	0.0238 (16)	0.0306 (17)	0.0213 (16)	−0.0054 (14)	0.0028 (13)	−0.0047 (14)
O52	0.0240 (15)	0.0239 (16)	0.0241 (15)	−0.0086 (13)	0.0034 (12)	−0.0050 (13)
C53	0.022 (2)	0.024 (2)	0.025 (2)	−0.0053 (19)	0.0047 (18)	0.001 (2)
C54	0.032 (3)	0.036 (3)	0.048 (3)	−0.013 (2)	0.016 (2)	−0.010 (2)

Geometric parameters (Å, º)

S1—C2	1.721 (4)	C28—H28	0.95
S1—C5	1.749 (4)	C29—H29	0.95
C2—N3	1.308 (5)	C41—C44	1.523 (6)
C2—N21	1.387 (5)	C41—C42	1.531 (5)
N3—C4	1.376 (5)	C41—C43	1.540 (6)
C4—C5	1.385 (6)	C42—H421	0.98
C4—C41	1.529 (5)	C42—H422	0.98
C5—C51	1.463 (5)	C42—H423	0.98
N21—C22	1.389 (5)	C43—H431	0.98
N21—H21	0.82 (4)	C43—H432	0.98
C22—O22	1.229 (4)	C43—H433	0.98
C22—N23	1.356 (5)	C44—H441	0.98
N23—C24	1.418 (5)	C44—H442	0.98
N23—H23	0.99 (4)	C44—H443	0.98
C24—C29	1.385 (6)	C51—O51	1.215 (4)
C24—C25	1.400 (6)	C51—O52	1.350 (5)
C25—C26	1.381 (6)	O52—C53	1.464 (5)
C25—H25	0.95	C53—C54	1.504 (6)
C26—C27	1.378 (6)	C53—H531	0.99
C26—H26	0.95	C53—H532	0.99
C27—C28	1.394 (6)	C54—H541	0.98
C27—H27	0.95	C54—H542	0.98
C28—C29	1.374 (6)	C54—H543	0.98
C2—S1—C5	88.4 (2)	C44—C41—C42	108.3 (3)
N3—C2—N21	122.9 (4)	C4—C41—C42	108.9 (3)
N3—C2—S1	115.4 (3)	C44—C41—C43	110.5 (3)
N21—C2—S1	121.8 (3)	C4—C41—C43	109.2 (3)
C2—N3—C4	112.4 (3)	C42—C41—C43	108.1 (3)
N3—C4—C5	113.1 (3)	C41—C42—H421	109.5
N3—C4—C41	117.4 (3)	C41—C42—H422	109.5
C5—C4—C41	129.5 (4)	H421—C42—H422	109.5
C4—C5—C51	131.5 (4)	C41—C42—H423	109.5
C4—C5—S1	110.6 (3)	H421—C42—H423	109.5
C51—C5—S1	117.8 (3)	H422—C42—H423	109.5
C2—N21—C22	129.1 (4)	C41—C43—H431	109.5
C2—N21—H21	115 (3)	C41—C43—H432	109.5
C22—N21—H21	116 (3)	H431—C43—H432	109.5
O22—C22—N23	125.2 (4)	C41—C43—H433	109.5
O22—C22—N21	119.3 (3)	H431—C43—H433	109.5
N23—C22—N21	115.5 (3)	H432—C43—H433	109.5
C22—N23—C24	128.0 (3)	C41—C44—H441	109.5
C22—N23—H23	109 (2)	C41—C44—H442	109.5
C24—N23—H23	122 (2)	H441—C44—H442	109.5
C29—C24—C25	119.3 (4)	C41—C44—H443	109.5
C29—C24—N23	117.0 (4)	H441—C44—H443	109.5
C25—C24—N23	123.7 (4)	H442—C44—H443	109.5
C26—C25—C24	118.9 (4)	O51—C51—O52	122.4 (4)
C26—C25—H25	120.5	O51—C51—C5	126.5 (4)
C24—C25—H25	120.5	O52—C51—C5	111.0 (3)
C27—C26—C25	121.7 (4)	C51—O52—C53	115.5 (3)
C27—C26—H26	119.1	O52—C53—C54	107.2 (3)
C25—C26—H26	119.1	O52—C53—H531	110.3
C26—C27—C28	119.2 (4)	C54—C53—H531	110.3
C26—C27—H27	120.4	O52—C53—H532	110.3
C28—C27—H27	120.4	C54—C53—H532	110.3
C29—C28—C27	119.6 (4)	H531—C53—H532	108.5
C29—C28—H28	120.2	C53—C54—H541	109.5
C27—C28—H28	120.2	C53—C54—H542	109.5
C28—C29—C24	121.3 (4)	H541—C54—H542	109.5
C28—C29—H29	119.4	C53—C54—H543	109.5
C24—C29—H29	119.4	H541—C54—H543	109.5
C44—C41—C4	111.7 (3)	H542—C54—H543	109.5
C5—S1—C2—N3	−0.5 (3)	N23—C24—C25—C26	−177.9 (4)
C5—S1—C2—N21	−179.7 (4)	C24—C25—C26—C27	−1.0 (6)
N21—C2—N3—C4	179.3 (4)	C25—C26—C27—C28	0.8 (6)
S1—C2—N3—C4	0.1 (4)	C26—C27—C28—C29	−0.3 (6)
C2—N3—C4—C5	0.5 (5)	C27—C28—C29—C24	0.0 (6)
C2—N3—C4—C41	−179.2 (3)	C25—C24—C29—C28	−0.2 (6)
N3—C4—C5—C51	176.5 (4)	N23—C24—C29—C28	178.5 (4)
C41—C4—C5—C51	−3.9 (7)	N3—C4—C41—C44	126.8 (4)
N3—C4—C5—S1	−0.8 (4)	C5—C4—C41—C44	−52.8 (5)
C41—C4—C5—S1	178.8 (3)	N3—C4—C41—C42	7.2 (5)
C2—S1—C5—C4	0.7 (3)	C5—C4—C41—C42	−172.4 (4)
C2—S1—C5—C51	−177.0 (3)	N3—C4—C41—C43	−110.7 (4)
N3—C2—N21—C22	−2.6 (7)	C5—C4—C41—C43	69.7 (5)
S1—C2—N21—C22	176.6 (3)	C4—C5—C51—O51	−0.6 (7)
C2—N21—C22—O22	179.5 (4)	S1—C5—C51—O51	176.6 (3)
C2—N21—C22—N23	−1.5 (6)	C4—C5—C51—O52	−179.1 (4)
O22—C22—N23—C24	2.0 (6)	S1—C5—C51—O52	−1.9 (4)
N21—C22—N23—C24	−176.9 (4)	O51—C51—O52—C53	2.0 (5)
C22—N23—C24—C29	156.1 (4)	C5—C51—O52—C53	−179.5 (3)
C22—N23—C24—C25	−25.3 (6)	C51—O52—C53—C54	−168.5 (3)
C29—C24—C25—C26	0.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O22^i	0.82 (4)	2.03 (4)	2.821 (5)	159 (4)
N23—H23···N3	0.99 (4)	1.79 (4)	2.677 (5)	148 (3)
C25—H25···O22	0.95	2.44	2.966 (5)	115
C43—H432···O51	0.98	2.50	3.262 (5)	135
C44—H442···O51	0.98	2.22	3.061 (5)	143

Symmetry code: (i) x−1/2, −y−1/2, −z.