Ethyl 4-phenyl-2-(N-pyrrolyl)-1,3-thia­zole-5-carboxyl­ate

The structure of the title compound, C₁₆H₁₄N₂O₂S, comprises a twisted mol­ecule with dihedral angles of 11.3 (2) and 45.8 (1)° between the thia­zole and, respectively, the pyrrole and phenyl rings.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.080
• wR factor = 0.206
• Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



RINTA_01  Alert B The value of Rint is greater than 0.15
          Rint given   0.171


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      1.258
          Test value =      1.200

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

PLAT_213  Alert C Atom C44     has ADP max/min Ratio ...........       3.10 prolate


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 3 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-phenyl-2-(N-pyrrole)-1,3-thiazole-5-carboxylate

Crystal data

C16H14N2O2S	F(000) = 624
Mr = 298.35	Dx = 1.399 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2375 (4) Å	Cell parameters from 6999 reflections
b = 3.9460 (2) Å	θ = 2.9–27.5°
c = 35.075 (2) Å	µ = 0.23 mm^−1
β = 91.979 (2)°	T = 150 K
V = 1416.1 (1) Å^3	Needle, colourless
Z = 4	0.30 × 0.08 × 0.03 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2486 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1643 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.171
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −4→4
Tmin = 0.933, Tmax = 0.993	l = −37→41
6999 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.206	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1059P)^2] where P = (Fo^2 + 2Fc^2)/3
2486 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 1.26 e Å^−3
0 restraints	Δρmin = −0.95 e Å^−3

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)

0.3886 (0.0224) x - 3.4319 (0.0042) y - 17.2954 (0.0663) z = 3.9004 (0.0236)

* -0.0022 (0.0025) N21 * 0.0032 (0.0026) C22 * -0.0029 (0.0026) C23 * 0.0015 (0.0027) C24 * 0.0004 (0.0027) C25

Rms deviation of fitted atoms = 0.0023

- 1.3213 (0.0131) x - 3.5855 (0.0030) y - 13.7648 (0.0560) z = 1.8416 (0.0124)

Angle to previous plane (with approximate e.s.d.) = 11.25 (0.21)

* -0.0067 (0.0017) S1 * 0.0074 (0.0021) C2 * -0.0041 (0.0023) N3 * -0.0026 (0.0025) C4 * 0.0060 (0.0022) C5

Rms deviation of fitted atoms = 0.0057

2.4471 (0.0176) x + 3.5361 (0.0031) y - 13.3969 (0.0579) z = 2.8904 (0.0252)

Angle to previous plane (with approximate e.s.d.) = 45.84 (0.10)

* -0.0095 (0.0029) C41 * 0.0079 (0.0030) C42 * 0.0010 (0.0031) C43 * -0.0085 (0.0032) C44 * 0.0068 (0.0032) C45 * 0.0021 (0.0030) C46

Rms deviation of fitted atoms = 0.0068

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

	x	y	z	Uiso*/Ueq
S1	0.19807 (9)	0.3277 (3)	0.12493 (3)	0.0257 (4)
C2	0.1169 (4)	0.2085 (9)	0.16478 (11)	0.0208 (9)
N21	0.1821 (3)	0.0576 (8)	0.19559 (9)	0.0242 (8)
C22	0.1239 (4)	−0.1010 (10)	0.22606 (11)	0.0283 (10)
H221	0.0326	−0.1253	0.2292	0.035*
C23	0.2183 (4)	−0.2138 (11)	0.25021 (13)	0.0327 (11)
H231	0.2058	−0.3334	0.2733	0.041*
C24	0.3403 (4)	−0.1227 (11)	0.23513 (13)	0.0382 (12)
H241	0.4239	−0.1697	0.2465	0.048*
C25	0.3173 (4)	0.0411 (12)	0.20204 (13)	0.0334 (11)
H251	0.3816	0.1301	0.1859	0.042*
N3	−0.0095 (3)	0.2549 (8)	0.16401 (9)	0.0214 (8)
C4	−0.0487 (3)	0.4007 (9)	0.12990 (11)	0.0211 (9)
C41	−0.1912 (3)	0.4820 (10)	0.12468 (11)	0.0258 (10)
C42	−0.2529 (4)	0.6344 (11)	0.15493 (13)	0.0330 (11)
H42	−0.2046	0.6832	0.1779	0.041*
C43	−0.3849 (4)	0.7157 (12)	0.15178 (15)	0.0422 (13)
H43	−0.4271	0.8222	0.1723	0.053*
C44	−0.4541 (4)	0.6392 (12)	0.11823 (16)	0.0460 (14)
H44	−0.5441	0.6968	0.1157	0.058*
C45	−0.3945 (4)	0.4810 (13)	0.08850 (14)	0.0445 (13)
H45	−0.4438	0.4257	0.0659	0.056*
C46	−0.2610 (4)	0.4013 (11)	0.09150 (12)	0.0341 (11)
H46	−0.2191	0.2934	0.0710	0.043*
C5	0.0493 (3)	0.4630 (10)	0.10490 (11)	0.0234 (9)
C51	0.0456 (4)	0.6397 (10)	0.06824 (12)	0.0270 (10)
O50	−0.0496 (3)	0.7489 (7)	0.05120 (8)	0.0332 (8)
O51	0.1690 (2)	0.6685 (7)	0.05504 (7)	0.0278 (7)
C52	0.1796 (4)	0.8394 (11)	0.01879 (12)	0.0328 (11)
H521	0.1273	1.0505	0.0184	0.041*
H522	0.1468	0.6915	−0.0022	0.041*
C53	0.3218 (4)	0.9196 (13)	0.01405 (14)	0.0428 (12)
H531	0.3724	0.7086	0.0143	0.054*
H532	0.3532	1.0651	0.0351	0.054*
H533	0.3325	1.0372	−0.0102	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0104 (5)	0.0355 (6)	0.0311 (6)	−0.0004 (4)	−0.0009 (4)	0.0007 (5)
C2	0.0152 (19)	0.021 (2)	0.026 (2)	0.0019 (17)	−0.0033 (17)	−0.0036 (18)
N21	0.0111 (16)	0.0267 (18)	0.034 (2)	0.0023 (14)	−0.0014 (14)	−0.0012 (16)
C22	0.021 (2)	0.030 (2)	0.034 (2)	−0.0007 (19)	0.0009 (19)	−0.001 (2)
C23	0.034 (3)	0.030 (2)	0.033 (3)	−0.001 (2)	−0.007 (2)	0.007 (2)
C24	0.023 (2)	0.042 (3)	0.048 (3)	0.006 (2)	−0.017 (2)	0.006 (2)
C25	0.0089 (19)	0.043 (3)	0.048 (3)	0.0012 (19)	−0.0045 (18)	0.002 (2)
N3	0.0094 (16)	0.0252 (18)	0.0293 (19)	−0.0007 (13)	−0.0020 (14)	−0.0008 (15)
C4	0.0100 (18)	0.022 (2)	0.031 (2)	−0.0010 (16)	−0.0032 (16)	−0.0012 (18)
C41	0.0120 (19)	0.025 (2)	0.040 (3)	−0.0015 (17)	−0.0024 (18)	0.008 (2)
C42	0.017 (2)	0.036 (3)	0.046 (3)	0.0040 (18)	0.0044 (19)	0.004 (2)
C43	0.019 (2)	0.043 (3)	0.066 (3)	0.009 (2)	0.011 (2)	0.005 (3)
C44	0.010 (2)	0.049 (3)	0.079 (4)	−0.003 (2)	0.002 (2)	0.022 (3)
C45	0.022 (2)	0.050 (3)	0.060 (3)	−0.008 (2)	−0.015 (2)	0.014 (3)
C46	0.019 (2)	0.041 (3)	0.042 (3)	−0.0047 (19)	−0.003 (2)	0.001 (2)
C5	0.0133 (19)	0.024 (2)	0.033 (2)	−0.0021 (17)	−0.0061 (17)	−0.0016 (19)
C51	0.023 (2)	0.028 (2)	0.030 (2)	−0.0044 (19)	−0.0017 (19)	−0.004 (2)
O50	0.0188 (16)	0.0446 (19)	0.0357 (18)	0.0031 (14)	−0.0051 (14)	0.0090 (15)
O51	0.0146 (14)	0.0395 (17)	0.0290 (16)	−0.0018 (13)	−0.0007 (12)	0.0032 (14)
C52	0.026 (2)	0.039 (3)	0.034 (3)	−0.005 (2)	0.0028 (19)	0.002 (2)
C53	0.029 (3)	0.050 (3)	0.051 (3)	−0.011 (2)	0.008 (2)	0.012 (3)

Geometric parameters (Å, º)

S1—C2	1.716 (4)	C42—H42	0.95
S1—C5	1.739 (4)	C43—C44	1.386 (7)
C2—N3	1.307 (5)	C43—H43	0.95
C2—N21	1.385 (5)	C44—C45	1.376 (7)
N21—C22	1.390 (5)	C44—H44	0.95
N21—C25	1.396 (5)	C45—C46	1.403 (6)
C22—C23	1.339 (6)	C45—H45	0.95
C22—H221	0.95	C46—H46	0.95
C23—C24	1.419 (6)	C5—C51	1.462 (6)
C23—H231	0.95	C51—O50	1.205 (5)
C24—C25	1.342 (6)	C51—O51	1.365 (5)
C24—H241	0.95	O51—C52	1.447 (5)
C25—H251	0.95	C52—C53	1.505 (5)
N3—C4	1.375 (5)	C52—H521	0.99
C4—C5	1.377 (5)	C52—H522	0.99
C4—C41	1.498 (5)	C53—H531	0.98
C41—C46	1.381 (6)	C53—H532	0.98
C41—C42	1.390 (6)	C53—H533	0.98
C42—C43	1.389 (6)
C2—S1—C5	88.37 (18)	C44—C43—H43	120.5
N3—C2—N21	121.8 (3)	C42—C43—H43	120.5
N3—C2—S1	116.9 (3)	C45—C44—C43	121.0 (4)
N21—C2—S1	121.3 (3)	C45—C44—H44	119.5
C2—N21—C22	125.9 (3)	C43—C44—H44	119.5
C2—N21—C25	126.5 (3)	C44—C45—C46	120.1 (4)
C22—N21—C25	107.6 (3)	C44—C45—H45	120.0
C23—C22—N21	108.5 (4)	C46—C45—H45	120.0
C23—C22—H221	125.7	C41—C46—C45	119.0 (4)
N21—C22—H221	125.7	C41—C46—H46	120.5
C22—C23—C24	107.7 (4)	C45—C46—H46	120.5
C22—C23—H231	126.1	C4—C5—C51	130.4 (4)
C24—C23—H231	126.1	C4—C5—S1	109.6 (3)
C25—C24—C23	108.3 (4)	C51—C5—S1	119.8 (3)
C25—C24—H241	125.8	O50—C51—O51	123.0 (4)
C23—C24—H241	125.8	O50—C51—C5	127.0 (4)
C24—C25—N21	107.8 (4)	O51—C51—C5	110.0 (3)
C24—C25—H251	126.1	C51—O51—C52	115.8 (3)
N21—C25—H251	126.1	O51—C52—C53	107.3 (3)
C2—N3—C4	109.6 (3)	O51—C52—H521	110.3
N3—C4—C5	115.5 (3)	C53—C52—H521	110.3
N3—C4—C41	116.7 (3)	O51—C52—H522	110.3
C5—C4—C41	127.7 (4)	C53—C52—H522	110.3
C46—C41—C42	120.5 (4)	H521—C52—H522	108.5
C46—C41—C4	121.8 (4)	C52—C53—H531	109.5
C42—C41—C4	117.7 (4)	C52—C53—H532	109.5
C43—C42—C41	120.4 (4)	H531—C53—H532	109.5
C43—C42—H42	119.8	C52—C53—H533	109.5
C41—C42—H42	119.8	H531—C53—H533	109.5
C44—C43—C42	119.0 (5)	H532—C53—H533	109.5
C5—S1—C2—N3	1.2 (3)	C46—C41—C42—C43	−1.7 (6)
C5—S1—C2—N21	178.6 (3)	C4—C41—C42—C43	180.0 (4)
N3—C2—N21—C22	9.2 (6)	C41—C42—C43—C44	0.7 (7)
S1—C2—N21—C22	−168.0 (3)	C42—C43—C44—C45	0.9 (7)
N3—C2—N21—C25	−169.7 (4)	C43—C44—C45—C46	−1.4 (7)
S1—C2—N21—C25	13.0 (5)	C42—C41—C46—C45	1.2 (6)
C2—N21—C22—C23	−179.6 (4)	C4—C41—C46—C45	179.4 (4)
C25—N21—C22—C23	−0.5 (5)	C44—C45—C46—C41	0.4 (7)
N21—C22—C23—C24	0.6 (5)	N3—C4—C5—C51	−173.8 (4)
C22—C23—C24—C25	−0.4 (5)	C41—C4—C5—C51	4.3 (7)
C23—C24—C25—N21	0.1 (5)	N3—C4—C5—S1	0.7 (4)
C2—N21—C25—C24	179.4 (4)	C41—C4—C5—S1	178.8 (3)
C22—N21—C25—C24	0.3 (5)	C2—S1—C5—C4	−1.0 (3)
N21—C2—N3—C4	−178.4 (3)	C2—S1—C5—C51	174.2 (3)
S1—C2—N3—C4	−1.0 (4)	C4—C5—C51—O50	−5.5 (7)
C2—N3—C4—C5	0.2 (5)	S1—C5—C51—O50	−179.5 (3)
C2—N3—C4—C41	−178.1 (3)	C4—C5—C51—O51	174.3 (4)
N3—C4—C41—C46	−133.9 (4)	S1—C5—C51—O51	0.3 (5)
C5—C4—C41—C46	48.0 (6)	O50—C51—O51—C52	−0.1 (6)
N3—C4—C41—C42	44.3 (5)	C5—C51—O51—C52	−180.0 (3)
C5—C4—C41—C42	−133.8 (4)	C51—O51—C52—C53	166.5 (4)