(Z)-2-(3-Thien­yl)-3-(3,4,5-trimethoxy­phenyl)acrylonitrile

The title compound, C₁₆H₁₅NO₃S, was prepared by base-catalyzed reaction of 3,4,5-trimethoxy­benzaldehyde with thio­phene-3-acetonitrile. The olefinic bond has Z geometry and thien­yl ring flip disorder is observed.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.087
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C13    ...       1.45 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.07

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           27.49
           From the CIF: _reflns_number_total               3337
           Count of symmetry unique reflns         1953
           Completeness (_total/calc)            170.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1384
           Fraction of Friedel pairs measured     0.709
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local programs.

(Z)-2-(3-Thienyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile

Crystal data

C16H15NO3S	F(000) = 632
Mr = 301.35	Dx = 1.367 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1966 reflections
a = 6.9281 (2) Å	θ = 1.0–27.5°
b = 8.6629 (2) Å	µ = 0.23 mm^−1
c = 24.3962 (7) Å	T = 90 K
V = 1464.20 (7) Å^3	Block, pale yellow
Z = 4	0.32 × 0.25 × 0.15 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3337 independent reflections
Radiation source: fine-focus sealed tube	2787 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 1.7°
ω scans at fixed χ = 55°	h = −8→8
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.910, Tmax = 0.966	l = −31→31
3337 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 0.6118P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.087	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.22 e Å^−3
3337 reflections	Δρmin = −0.22 e Å^−3
210 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
195 restraints	Extinction coefficient: 0.0151 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1386 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.94380 (19)	0.78060 (16)	0.34488 (5)	0.0240 (3)
O2	0.94461 (18)	0.74666 (15)	0.23578 (5)	0.0207 (3)
O3	0.70118 (19)	0.56044 (15)	0.18504 (5)	0.0209 (3)
C1	0.5328 (3)	0.5131 (2)	0.32830 (7)	0.0176 (4)
C2	0.6702 (3)	0.6052 (2)	0.35459 (7)	0.0177 (4)
H2	0.6694	0.6148	0.3934	0.021*
C3	0.8077 (3)	0.6826 (2)	0.32359 (8)	0.0177 (4)
C4	0.8128 (3)	0.6660 (2)	0.26686 (7)	0.0166 (4)
C5	0.6809 (3)	0.5689 (2)	0.24082 (7)	0.0161 (4)
C6	0.5409 (3)	0.4923 (2)	0.27126 (7)	0.0176 (4)
H6	0.4511	0.4261	0.2535	0.021*
C7	0.3692 (3)	0.4406 (2)	0.35634 (8)	0.0194 (4)
H7	0.3146	0.3544	0.3380	0.023*
C8	0.2842 (3)	0.4780 (2)	0.40446 (7)	0.0172 (4)
C9	0.108 (6)	0.406 (6)	0.427 (2)	0.0174 (10)	0.463 (2)
C10	0.026 (3)	0.275 (3)	0.4010 (10)	0.0211 (11)	0.463 (2)
H10	0.0803	0.2245	0.3700	0.025*	0.463 (2)
S1	−0.1864 (3)	0.2210 (3)	0.43350 (11)	0.0264 (4)	0.463 (2)
C11	−0.1528 (17)	0.3658 (15)	0.4827 (6)	0.0261 (4)	0.463 (2)
H11	−0.2328	0.3801	0.5139	0.031*	0.463 (2)
C12	−0.004 (2)	0.451 (2)	0.4710 (9)	0.0195 (12)	0.463 (2)
H12	0.0255	0.5408	0.4917	0.023*	0.463 (2)
C9'	0.107 (5)	0.402 (5)	0.4248 (19)	0.0174 (10)	0.537 (2)
C10'	0.0229 (19)	0.455 (2)	0.4741 (7)	0.0195 (12)	0.537 (2)
H10'	0.0749	0.5337	0.4970	0.023*	0.537 (2)
S1'	−0.1884 (3)	0.3566 (3)	0.48640 (11)	0.0261 (4)	0.537 (2)
C11'	−0.1460 (13)	0.2369 (13)	0.4301 (4)	0.0264 (4)	0.537 (2)
H11'	−0.2237	0.1505	0.4207	0.032*	0.537 (2)
C12'	0.006 (3)	0.281 (3)	0.4022 (9)	0.0211 (11)	0.537 (2)
H12'	0.0437	0.2324	0.3690	0.025*	0.537 (2)
C13	0.3549 (3)	0.6046 (2)	0.43739 (8)	0.0229 (4)
N1	0.4029 (3)	0.7067 (2)	0.46410 (8)	0.0364 (5)
C14	0.9267 (3)	0.8182 (2)	0.40168 (8)	0.0236 (4)
H14A	0.7993	0.8632	0.4086	0.035*
H14B	1.0270	0.8928	0.4117	0.035*
H14C	0.9421	0.7243	0.4237	0.035*
C15	1.1292 (3)	0.6708 (3)	0.23374 (9)	0.0264 (5)
H15A	1.1843	0.6661	0.2707	0.040*
H15B	1.2161	0.7286	0.2096	0.040*
H15C	1.1128	0.5658	0.2195	0.040*
C16	0.5765 (3)	0.4571 (3)	0.15677 (8)	0.0274 (5)
H16A	0.5950	0.3522	0.1709	0.041*
H16B	0.6066	0.4591	0.1175	0.041*
H16C	0.4422	0.4886	0.1624	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0237 (7)	0.0262 (7)	0.0219 (7)	−0.0083 (7)	−0.0023 (6)	−0.0037 (6)
O2	0.0180 (6)	0.0203 (7)	0.0240 (7)	−0.0013 (6)	0.0027 (5)	0.0029 (6)
O3	0.0236 (7)	0.0231 (7)	0.0160 (6)	−0.0049 (6)	0.0017 (6)	−0.0016 (5)
C1	0.0179 (8)	0.0145 (9)	0.0204 (9)	0.0012 (8)	0.0018 (8)	0.0024 (8)
C2	0.0190 (9)	0.0183 (9)	0.0159 (9)	0.0017 (8)	−0.0011 (8)	−0.0006 (7)
C3	0.0165 (8)	0.0144 (9)	0.0223 (10)	−0.0010 (8)	−0.0023 (8)	−0.0005 (7)
C4	0.0151 (8)	0.0148 (8)	0.0200 (9)	0.0010 (8)	0.0017 (8)	0.0030 (7)
C5	0.0167 (8)	0.0167 (9)	0.0149 (8)	0.0018 (8)	0.0008 (7)	0.0001 (7)
C6	0.0181 (8)	0.0161 (9)	0.0185 (9)	−0.0011 (8)	0.0002 (7)	−0.0014 (7)
C7	0.0232 (10)	0.0158 (9)	0.0192 (10)	−0.0001 (8)	−0.0013 (8)	−0.0006 (8)
C8	0.0195 (9)	0.0160 (9)	0.0160 (9)	0.0003 (8)	−0.0017 (7)	0.0004 (7)
C9	0.0194 (9)	0.0159 (16)	0.017 (3)	0.0028 (8)	0.0003 (13)	0.0033 (16)
C10	0.022 (3)	0.0213 (15)	0.0205 (11)	−0.001 (2)	0.0036 (16)	−0.0002 (9)
S1	0.0249 (11)	0.0254 (8)	0.0287 (6)	−0.0066 (7)	0.0109 (7)	−0.0031 (5)
C11	0.0288 (10)	0.0228 (6)	0.0268 (6)	−0.0039 (6)	0.0106 (6)	0.0012 (4)
C12	0.019 (3)	0.0204 (11)	0.0194 (17)	0.0016 (18)	0.001 (2)	0.0012 (10)
C9'	0.0194 (9)	0.0159 (16)	0.017 (3)	0.0028 (8)	0.0003 (13)	0.0033 (16)
C10'	0.019 (3)	0.0204 (11)	0.0194 (17)	0.0016 (18)	0.001 (2)	0.0012 (10)
S1'	0.0288 (10)	0.0228 (6)	0.0268 (6)	−0.0039 (6)	0.0106 (6)	0.0012 (4)
C11'	0.0249 (11)	0.0254 (8)	0.0287 (6)	−0.0066 (7)	0.0109 (7)	−0.0031 (5)
C12'	0.022 (3)	0.0213 (15)	0.0205 (11)	−0.001 (2)	0.0036 (16)	−0.0002 (9)
C13	0.0197 (10)	0.0244 (10)	0.0247 (10)	−0.0031 (8)	0.0040 (8)	−0.0007 (9)
N1	0.0363 (10)	0.0388 (11)	0.0339 (10)	−0.0105 (9)	0.0073 (9)	−0.0151 (9)
C14	0.0257 (11)	0.0246 (10)	0.0206 (10)	−0.0003 (9)	−0.0033 (8)	−0.0039 (8)
C15	0.0176 (9)	0.0307 (11)	0.0311 (12)	−0.0034 (9)	0.0025 (8)	0.0008 (9)
C16	0.0256 (10)	0.0335 (12)	0.0230 (11)	−0.0052 (10)	−0.0006 (8)	−0.0081 (9)

Geometric parameters (Å, º)

O1—C3	1.371 (2)	C10—H10	0.9500
O1—C14	1.428 (2)	S1—C11	1.752 (12)
O2—C4	1.377 (2)	C11—C12	1.298 (17)
O2—C15	1.439 (2)	C11—H11	0.9500
O3—C5	1.370 (2)	C12—H12	0.9500
O3—C16	1.422 (2)	C9'—C12'	1.38 (4)
C1—C2	1.398 (3)	C9'—C10'	1.41 (4)
C1—C6	1.404 (2)	C10'—S1'	1.722 (11)
C1—C7	1.465 (3)	C10'—H10'	0.9500
C2—C3	1.389 (3)	S1'—C11'	1.747 (9)
C2—H2	0.9500	C11'—C12'	1.309 (15)
C3—C4	1.392 (2)	C11'—H11'	0.9500
C4—C5	1.396 (3)	C12'—H12'	0.9500
C5—C6	1.390 (3)	C13—N1	1.148 (3)
C6—H6	0.9500	C14—H14A	0.9800
C7—C8	1.353 (3)	C14—H14B	0.9800
C7—H7	0.9500	C14—H14C	0.9800
C8—C13	1.445 (3)	C15—H15A	0.9800
C8—C9'	1.474 (8)	C15—H15B	0.9800
C8—C9	1.481 (9)	C15—H15C	0.9800
C9—C12	1.38 (4)	C16—H16A	0.9800
C9—C10	1.42 (4)	C16—H16B	0.9800
C10—S1	1.739 (15)	C16—H16C	0.9800
C3—O1—C14	116.85 (15)	C12—C11—H11	124.4
C4—O2—C15	112.12 (14)	S1—C11—H11	124.4
C5—O3—C16	116.93 (15)	C11—C12—C9	117.1 (18)
C2—C1—C6	120.02 (17)	C11—C12—H12	121.5
C2—C1—C7	123.86 (17)	C9—C12—H12	121.5
C6—C1—C7	116.03 (17)	C12'—C9'—C10'	112.0 (7)
C3—C2—C1	119.53 (17)	C12'—C9'—C8	129 (3)
C3—C2—H2	120.2	C10'—C9'—C8	119 (3)
C1—C2—H2	120.2	C9'—C10'—S1'	109.9 (12)
O1—C3—C2	124.36 (17)	C9'—C10'—H10'	125.1
O1—C3—C4	115.02 (16)	S1'—C10'—H10'	125.1
C2—C3—C4	120.61 (17)	C10'—S1'—C11'	90.8 (6)
O2—C4—C3	120.81 (17)	C12'—C11'—S1'	111.8 (9)
O2—C4—C5	119.30 (16)	C12'—C11'—H11'	124.1
C3—C4—C5	119.88 (17)	S1'—C11'—H11'	124.1
O3—C5—C6	125.23 (17)	C11'—C12'—C9'	115.1 (16)
O3—C5—C4	114.66 (16)	C11'—C12'—H12'	122.4
C6—C5—C4	120.10 (16)	C9'—C12'—H12'	122.4
C5—C6—C1	119.76 (17)	N1—C13—C8	177.1 (2)
C5—C6—H6	120.1	O1—C14—H14A	109.5
C1—C6—H6	120.1	O1—C14—H14B	109.5
C8—C7—C1	129.74 (18)	H14A—C14—H14B	109.5
C8—C7—H7	115.1	O1—C14—H14C	109.5
C1—C7—H7	115.1	H14A—C14—H14C	109.5
C7—C8—C13	121.11 (18)	H14B—C14—H14C	109.5
C7—C8—C9'	123.2 (16)	O2—C15—H15A	109.5
C13—C8—C9'	115.6 (16)	O2—C15—H15B	109.5
C7—C8—C9	125.7 (19)	H15A—C15—H15B	109.5
C13—C8—C9	113.1 (18)	O2—C15—H15C	109.5
C12—C9—C10	110.7 (8)	H15A—C15—H15C	109.5
C12—C9—C8	129 (3)	H15B—C15—H15C	109.5
C10—C9—C8	120 (3)	O3—C16—H16A	109.5
C9—C10—S1	110.3 (14)	O3—C16—H16B	109.5
C9—C10—H10	124.9	H16A—C16—H16B	109.5
S1—C10—H10	124.9	O3—C16—H16C	109.5
C10—S1—C11	90.4 (7)	H16A—C16—H16C	109.5
C12—C11—S1	111.2 (11)	H16B—C16—H16C	109.5
C6—C1—C2—C3	3.5 (3)	C7—C8—C9—C12	−169 (4)
C7—C1—C2—C3	−172.94 (17)	C13—C8—C9—C12	7 (8)
C14—O1—C3—C2	−7.6 (3)	C9'—C8—C9—C12	−159 (100)
C14—O1—C3—C4	171.35 (17)	C7—C8—C9—C10	7 (7)
C1—C2—C3—O1	177.28 (17)	C13—C8—C9—C10	−177 (4)
C1—C2—C3—C4	−1.7 (3)	C9'—C8—C9—C10	17 (100)
C15—O2—C4—C3	83.6 (2)	C12—C9—C10—S1	0 (6)
C15—O2—C4—C5	−97.6 (2)	C8—C9—C10—S1	−176 (4)
O1—C3—C4—O2	−1.3 (3)	C9—C10—S1—C11	−3 (4)
C2—C3—C4—O2	177.74 (16)	C10—S1—C11—C12	5.3 (19)
O1—C3—C4—C5	179.90 (16)	S1—C11—C12—C9	−6 (4)
C2—C3—C4—C5	−1.1 (3)	C10—C9—C12—C11	4 (6)
C16—O3—C5—C6	−4.3 (3)	C8—C9—C12—C11	−180 (5)
C16—O3—C5—C4	176.96 (16)	C7—C8—C9'—C12'	4 (7)
O2—C4—C5—O3	1.8 (2)	C13—C8—C9'—C12'	179 (4)
C3—C4—C5—O3	−179.32 (17)	C9—C8—C9'—C12'	−167 (100)
O2—C4—C5—C6	−176.93 (17)	C7—C8—C9'—C10'	−176 (3)
C3—C4—C5—C6	1.9 (3)	C13—C8—C9'—C10'	−1 (5)
O3—C5—C6—C1	−178.65 (17)	C9—C8—C9'—C10'	13 (100)
C4—C5—C6—C1	0.0 (3)	C12'—C9'—C10'—S1'	−4 (5)
C2—C1—C6—C5	−2.7 (3)	C8—C9'—C10'—S1'	176 (3)
C7—C1—C6—C5	174.04 (16)	C9'—C10'—S1'—C11'	5 (3)
C2—C1—C7—C8	21.3 (3)	C10'—S1'—C11'—C12'	−5.7 (18)
C6—C1—C7—C8	−155.28 (19)	S1'—C11'—C12'—C9'	4 (4)
C1—C7—C8—C13	−1.3 (3)	C10'—C9'—C12'—C11'	0 (6)
C1—C7—C8—C9'	174 (3)	C8—C9'—C12'—C11'	179 (4)
C1—C7—C8—C9	174 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2^i	0.95	2.59	3.35 (2)	137
C10—H10···O3^i	0.95	2.47	3.380 (19)	160
C12—H12···N1^ii	0.95	2.58	3.422 (19)	148

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z+1.