N-(3,5-Dimethoxy­benzyl­idene)-2-(methyl­sulfan­yl)aniline

The title compound, C₁₆H₁₇NO₂S, has a trans geometry about the C=N bond. The mol­ecule is non-planar, with a dihedral angle of 55.21 (4)° between the two aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.086
• Data-to-parameter ratio = 18.0

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           27.44
           From the CIF: _reflns_number_total               3285
           Count of symmetry unique reflns         1767
           Completeness (_total/calc)            185.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1518
           Fraction of Friedel pairs measured     0.859
           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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

N-(3,5-Dimethoxybenzylidene)-2-(methylsulfanyl)aniline

Crystal data

C16H17NO2S	F(000) = 304
Mr = 287.37	Dx = 1.325 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 7.7704 (18) Å	θ = 5.9–14.2°
b = 7.8397 (9) Å	µ = 0.23 mm^−1
c = 12.0141 (15) Å	T = 173 K
β = 100.230 (14)°	Prism, yellow
V = 720.2 (2) Å^3	0.48 × 0.41 × 0.35 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer	3185 reflections with I > 2σ(I)
non–profiled ω/2θ scans	Rint = 0.024
Absorption correction: ψ scan (North et al., 1968)	θmax = 27.4°, θmin = 1.7°
Tmin = 0.900, Tmax = 0.925	h = −10→10
3780 measured reflections	k = −10→10
3285 independent reflections	l = −15→15

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 0.0994P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.032	(Δ/σ)max = 0.001
wR(F^2) = 0.086	Δρmax = 0.29 e Å^−3
S = 1.05	Δρmin = −0.25 e Å^−3
3285 reflections	Absolute structure: Flack (1983), 1518 Friedel pairs
182 parameters	Absolute structure parameter: 0.02 (6)
1 restraint

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.

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

	x	y	z	Uiso*/Ueq
C1	−0.1014 (2)	0.2613 (2)	−0.12109 (15)	0.0310 (3)
H1A	−0.1653	0.3593	−0.1586	0.046*
H1B	−0.173	0.2049	−0.0726	0.046*
H1C	−0.0758	0.1806	−0.1782	0.046*
C10	0.20900 (18)	0.42546 (17)	−0.13818 (12)	0.0202 (3)
C11	0.14963 (19)	0.41892 (18)	−0.25468 (12)	0.0237 (3)
H11	0.0416	0.3645	−0.2833	0.028*
C12	0.2460 (2)	0.4907 (2)	−0.32941 (12)	0.0265 (3)
H12	0.2036	0.4859	−0.4085	0.032*
C13	0.4046 (2)	0.5697 (2)	−0.28843 (13)	0.0265 (3)
H13	0.4706	0.6196	−0.3394	0.032*
C14	0.46646 (19)	0.57561 (19)	−0.17284 (12)	0.0232 (3)
H14	0.5752	0.6293	−0.1451	0.028*
C15	0.37102 (17)	0.50387 (17)	−0.09721 (11)	0.0194 (2)
C20	0.58546 (18)	0.48023 (18)	0.06170 (11)	0.0211 (3)
H20	0.6595	0.4438	0.0113	0.025*
C21	0.65980 (17)	0.49551 (17)	0.18222 (11)	0.0200 (3)
C22	0.82824 (18)	0.43370 (17)	0.21886 (12)	0.0220 (3)
H22	0.8923	0.384	0.1667	0.026*
C23	0.90136 (18)	0.44576 (18)	0.33309 (12)	0.0239 (3)
C24	0.8091 (2)	0.5204 (2)	0.40877 (11)	0.0253 (3)
H24	0.8607	0.5298	0.4864	0.03*
C25	0.64011 (18)	0.58192 (18)	0.37093 (11)	0.0221 (3)
C26	0.56351 (19)	0.56879 (18)	0.25750 (12)	0.0210 (3)
H26	0.4479	0.6089	0.2318	0.025*
C27	1.1601 (2)	0.2993 (2)	0.30618 (14)	0.0342 (4)
H27A	1.2742	0.2647	0.3489	0.051*
H27B	1.1772	0.3743	0.2438	0.051*
H27C	1.0945	0.1978	0.2757	0.051*
C28	0.3894 (2)	0.7201 (2)	0.41768 (13)	0.0308 (3)
H28A	0.3467	0.7661	0.4836	0.046*
H28B	0.3107	0.6295	0.3831	0.046*
H28C	0.3932	0.8113	0.3624	0.046*
N	0.42604 (16)	0.51353 (16)	0.02142 (9)	0.0217 (2)
O1	1.06487 (14)	0.38790 (17)	0.37906 (10)	0.0344 (3)
O2	0.56041 (15)	0.65213 (17)	0.45246 (8)	0.0313 (3)
S	0.09959 (4)	0.33291 (5)	−0.03654 (3)	0.02760 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0219 (7)	0.0321 (7)	0.0393 (9)	−0.0048 (6)	0.0062 (6)	−0.0045 (6)
C10	0.0203 (6)	0.0204 (6)	0.0200 (6)	0.0023 (5)	0.0040 (5)	−0.0024 (5)
C11	0.0223 (7)	0.0262 (7)	0.0205 (6)	0.0012 (5)	−0.0018 (5)	−0.0036 (5)
C12	0.0301 (7)	0.0298 (7)	0.0179 (6)	0.0026 (6)	−0.0005 (5)	−0.0005 (5)
C13	0.0281 (7)	0.0302 (7)	0.0219 (7)	0.0012 (6)	0.0063 (6)	0.0042 (6)
C14	0.0223 (6)	0.0238 (6)	0.0230 (7)	−0.0005 (5)	0.0024 (5)	−0.0013 (5)
C15	0.0197 (6)	0.0208 (6)	0.0171 (6)	0.0039 (5)	0.0013 (5)	−0.0030 (5)
C20	0.0211 (6)	0.0238 (6)	0.0187 (6)	−0.0007 (5)	0.0040 (5)	−0.0025 (5)
C21	0.0206 (6)	0.0209 (6)	0.0182 (6)	−0.0030 (5)	0.0026 (5)	0.0006 (5)
C22	0.0205 (6)	0.0249 (7)	0.0208 (6)	−0.0019 (5)	0.0042 (5)	0.0002 (5)
C23	0.0192 (7)	0.0273 (7)	0.0236 (7)	−0.0023 (5)	−0.0009 (5)	0.0041 (5)
C24	0.0255 (7)	0.0323 (7)	0.0166 (6)	−0.0036 (6)	−0.0003 (5)	0.0027 (5)
C25	0.0241 (7)	0.0250 (6)	0.0174 (6)	−0.0031 (5)	0.0044 (5)	−0.0002 (5)
C26	0.0192 (6)	0.0242 (6)	0.0190 (6)	−0.0019 (5)	0.0016 (5)	0.0002 (5)
C27	0.0234 (7)	0.0388 (9)	0.0382 (8)	0.0067 (6)	−0.0005 (6)	0.0045 (7)
C28	0.0318 (8)	0.0367 (8)	0.0251 (7)	0.0038 (6)	0.0083 (6)	−0.0033 (6)
N	0.0215 (5)	0.0264 (6)	0.0166 (5)	−0.0003 (4)	0.0014 (4)	−0.0040 (4)
O1	0.0224 (5)	0.0511 (7)	0.0268 (5)	0.0062 (5)	−0.0031 (4)	0.0019 (5)
O2	0.0320 (5)	0.0459 (7)	0.0162 (5)	0.0041 (5)	0.0045 (4)	−0.0043 (5)
S	0.02517 (17)	0.03598 (19)	0.02238 (16)	−0.00458 (15)	0.00619 (12)	−0.00092 (14)

Geometric parameters (Å, º)

C1—S	1.7955 (16)	C21—C22	1.3917 (19)
C1—H1A	0.98	C21—C26	1.396 (2)
C1—H1B	0.98	C22—C23	1.3922 (19)
C1—H1C	0.98	C22—H22	0.95
C10—C11	1.395 (2)	C23—O1	1.3696 (17)
C10—C15	1.4089 (18)	C23—C24	1.384 (2)
C10—S	1.7633 (14)	C24—C25	1.397 (2)
C11—C12	1.387 (2)	C24—H24	0.95
C11—H11	0.95	C25—O2	1.3644 (17)
C12—C13	1.389 (2)	C25—C26	1.3906 (19)
C12—H12	0.95	C26—H26	0.95
C13—C14	1.387 (2)	C27—O1	1.424 (2)
C13—H13	0.95	C27—H27A	0.98
C14—C15	1.390 (2)	C27—H27B	0.98
C14—H14	0.95	C27—H27C	0.98
C15—N	1.4154 (16)	C28—O2	1.423 (2)
C20—N	1.2744 (19)	C28—H28A	0.98
C20—C21	1.4655 (18)	C28—H28B	0.98
C20—H20	0.95	C28—H28C	0.98
S—C1—H1A	109.5	C21—C22—H22	120.5
S—C1—H1B	109.5	C23—C22—H22	120.5
H1A—C1—H1B	109.5	O1—C23—C24	115.26 (12)
S—C1—H1C	109.5	O1—C23—C22	124.19 (14)
H1A—C1—H1C	109.5	C24—C23—C22	120.55 (13)
H1B—C1—H1C	109.5	C23—C24—C25	119.92 (12)
C11—C10—C15	118.85 (13)	C23—C24—H24	120
C11—C10—S	124.44 (11)	C25—C24—H24	120
C15—C10—S	116.64 (10)	O2—C25—C26	124.30 (13)
C12—C11—C10	120.96 (13)	O2—C25—C24	115.21 (12)
C12—C11—H11	119.5	C26—C25—C24	120.49 (13)
C10—C11—H11	119.5	C25—C26—C21	118.69 (13)
C11—C12—C13	119.92 (13)	C25—C26—H26	120.7
C11—C12—H12	120	C21—C26—H26	120.7
C13—C12—H12	120	O1—C27—H27A	109.5
C14—C13—C12	119.83 (13)	O1—C27—H27B	109.5
C14—C13—H13	120.1	H27A—C27—H27B	109.5
C12—C13—H13	120.1	O1—C27—H27C	109.5
C13—C14—C15	120.72 (13)	H27A—C27—H27C	109.5
C13—C14—H14	119.6	H27B—C27—H27C	109.5
C15—C14—H14	119.6	O2—C28—H28A	109.5
C14—C15—C10	119.71 (12)	O2—C28—H28B	109.5
C14—C15—N	122.40 (12)	H28A—C28—H28B	109.5
C10—C15—N	117.81 (12)	O2—C28—H28C	109.5
N—C20—C21	122.99 (13)	H28A—C28—H28C	109.5
N—C20—H20	118.5	H28B—C28—H28C	109.5
C21—C20—H20	118.5	C20—N—C15	118.09 (12)
C22—C21—C26	121.37 (13)	C23—O1—C27	117.38 (12)
C22—C21—C20	117.88 (12)	C25—O2—C28	117.34 (11)
C26—C21—C20	120.75 (12)	C10—S—C1	102.41 (7)
C21—C22—C23	118.97 (13)
C15—C10—C11—C12	−1.2 (2)	O1—C23—C24—C25	−179.23 (13)
S—C10—C11—C12	−178.08 (11)	C22—C23—C24—C25	1.0 (2)
C10—C11—C12—C13	0.4 (2)	C23—C24—C25—O2	179.62 (13)
C11—C12—C13—C14	0.3 (2)	C23—C24—C25—C26	0.0 (2)
C12—C13—C14—C15	−0.3 (2)	O2—C25—C26—C21	179.41 (14)
C13—C14—C15—C10	−0.5 (2)	C24—C25—C26—C21	−1.0 (2)
C13—C14—C15—N	−177.29 (13)	C22—C21—C26—C25	1.0 (2)
C11—C10—C15—C14	1.21 (19)	C20—C21—C26—C25	−179.43 (12)
S—C10—C15—C14	178.38 (10)	C21—C20—N—C15	176.38 (13)
C11—C10—C15—N	178.13 (12)	C14—C15—N—C20	−46.1 (2)
S—C10—C15—N	−4.70 (16)	C10—C15—N—C20	137.10 (14)
N—C20—C21—C22	171.34 (14)	C24—C23—O1—C27	175.65 (14)
N—C20—C21—C26	−8.2 (2)	C22—C23—O1—C27	−4.6 (2)
C26—C21—C22—C23	0.0 (2)	C26—C25—O2—C28	−1.7 (2)
C20—C21—C22—C23	−179.60 (12)	C24—C25—O2—C28	178.64 (13)
C21—C22—C23—O1	179.29 (13)	C11—C10—S—C1	−6.42 (14)
C21—C22—C23—C24	−1.0 (2)	C15—C10—S—C1	176.59 (11)