N-[4-(Dimethyl­amino)benzyl­idene]-4-methyl­benzene­sulfonamide

The mol­ecule of the title compound, C₁₆H₁₈N₂O₂S, consists of essentially planar 4-(dimethyl­amino)benzyl­idene and 4-tol­yl fragments bonded through a sulfone S atom, which is approximately coplanar with both fragments. The mean planes of the MeC₆H₄S and Me₂NC₆H₄CH=NS groups are roughly orthogonal and form a dihedral angle of 101.28 (9)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.152
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     -   O1      ..       9.47 su

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C15     ..       5.41 su

   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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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.

N-[4-(Dimethylamino)benzylidene]-4-methylbenzenesulfonamide

Crystal data

C16H18N2O2S	F(000) = 640.00
Mr = 302.39	Dx = 1.324 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 9315 reflections
a = 17.1543 (4) Å	θ = 1.2–27.5°
b = 8.3835 (2) Å	µ = 0.22 mm^−1
c = 10.9679 (3) Å	T = 295 K
β = 105.976 (1)°	Prism, yellow
V = 1516.41 (6) Å^3	0.30 × 0.22 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1718 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.054
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→22
Tmin = 0.911, Tmax = 0.957	k = −10→10
9646 measured reflections	l = −14→13
3458 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0012Fo^2 + 1.0σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.055	(Δ/σ)max < 0.001
wR(F^2) = 0.152	Δρmax = 0.48 e Å^−3
S = 1.00	Δρmin = −0.39 e Å^−3
3176 reflections	Extinction correction: Larson (1970), equation 22
191 parameters	Extinction coefficient: 88.0 (23)
H-atom parameters constrained

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.20643 (4)	0.34121 (9)	0.71036 (7)	0.0720 (3)
O1	0.1752 (1)	0.1925 (2)	0.6523 (2)	0.0884 (8)
O2	0.2055 (1)	0.3699 (3)	0.8381 (2)	0.0942 (8)
N1	0.3005 (1)	0.3726 (3)	0.7073 (2)	0.0651 (7)
N2	0.6432 (1)	0.3441 (3)	0.5808 (2)	0.0640 (7)
C1	0.0369 (2)	0.8799 (4)	0.3781 (3)	0.091 (1)
C2	0.0796 (1)	0.7466 (4)	0.4614 (3)	0.0651 (9)
C3	0.0771 (2)	0.5939 (4)	0.4148 (3)	0.075 (1)
C4	0.1149 (2)	0.4680 (4)	0.4901 (3)	0.073 (1)
C5	0.1552 (1)	0.4969 (3)	0.6142 (2)	0.0567 (8)
C6	0.1593 (2)	0.6488 (4)	0.6620 (2)	0.0657 (9)
C7	0.1221 (2)	0.7738 (3)	0.5861 (3)	0.0662 (9)
C8	0.3274 (2)	0.2888 (3)	0.6290 (3)	0.0605 (8)
C9	0.4080 (1)	0.3053 (3)	0.6171 (2)	0.0549 (7)
C10	0.4627 (1)	0.4146 (3)	0.6885 (2)	0.0585 (8)
C11	0.5396 (1)	0.4293 (3)	0.6769 (2)	0.0559 (7)
C12	0.5666 (1)	0.3306 (3)	0.5915 (2)	0.0536 (7)
C13	0.5112 (1)	0.2213 (3)	0.5199 (2)	0.0592 (8)
C14	0.4342 (1)	0.2098 (3)	0.5316 (2)	0.0591 (8)
C15	0.6705 (2)	0.2481 (4)	0.4909 (3)	0.088 (1)
C16	0.6990 (2)	0.4582 (3)	0.6545 (3)	0.0748 (9)
H1	−0.0179	0.8862	0.3837	0.111*
H2	0.0643	0.9786	0.4063	0.111*
H3	0.0364	0.8599	0.2917	0.111*
H4	0.0476	0.5731	0.3262	0.087*
H5	0.1138	0.3603	0.4549	0.087*
H6	0.1893	0.6688	0.7505	0.077*
H7	0.1252	0.8821	0.6207	0.080*
H8	0.2912	0.2107	0.5752	0.071*
H9	0.4459	0.4827	0.7493	0.069*
H10	0.5766	0.5086	0.7277	0.065*
H11	0.5282	0.1510	0.4606	0.071*
H12	0.3966	0.1330	0.4788	0.070*
H13	0.6933	0.1505	0.5310	0.109*
H14	0.7107	0.3055	0.4627	0.109*
H15	0.6254	0.2243	0.4192	0.109*
H16	0.6701	0.5524	0.6663	0.089*
H17	0.7256	0.4128	0.7356	0.089*
H18	0.7387	0.4855	0.6110	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0667 (5)	0.0704 (6)	0.0837 (6)	0.0126 (4)	0.0285 (4)	0.0197 (4)
O1	0.072 (1)	0.058 (1)	0.139 (2)	−0.002 (1)	0.036 (1)	0.010 (1)
O2	0.100 (2)	0.115 (2)	0.077 (1)	0.035 (1)	0.040 (1)	0.038 (1)
N1	0.056 (1)	0.064 (2)	0.075 (1)	0.008 (1)	0.017 (1)	0.007 (1)
N2	0.062 (1)	0.061 (1)	0.072 (1)	−0.007 (1)	0.023 (1)	−0.006 (1)
C1	0.075 (2)	0.106 (3)	0.094 (2)	0.029 (2)	0.030 (2)	0.032 (2)
C2	0.054 (2)	0.073 (2)	0.071 (2)	0.010 (1)	0.022 (1)	0.014 (2)
C3	0.072 (2)	0.085 (2)	0.060 (2)	−0.004 (2)	0.004 (1)	−0.002 (2)
C4	0.079 (2)	0.061 (2)	0.076 (2)	−0.003 (1)	0.016 (2)	−0.010 (2)
C5	0.055 (1)	0.059 (2)	0.058 (2)	0.002 (1)	0.019 (1)	0.003 (1)
C6	0.068 (2)	0.071 (2)	0.053 (2)	0.004 (1)	0.009 (1)	−0.004 (1)
C7	0.065 (2)	0.059 (2)	0.076 (2)	0.009 (1)	0.022 (1)	0.001 (2)
C8	0.065 (2)	0.053 (2)	0.061 (2)	0.006 (1)	0.012 (1)	0.009 (1)
C9	0.057 (1)	0.049 (2)	0.058 (2)	0.004 (1)	0.015 (1)	0.010 (1)
C10	0.066 (2)	0.054 (2)	0.055 (1)	0.010 (1)	0.014 (1)	0.002 (1)
C11	0.058 (2)	0.049 (2)	0.054 (1)	−0.001 (1)	0.006 (1)	−0.004 (1)
C12	0.057 (1)	0.048 (1)	0.054 (1)	0.001 (1)	0.012 (1)	0.006 (1)
C13	0.068 (2)	0.050 (2)	0.060 (2)	−0.003 (1)	0.018 (1)	−0.008 (1)
C14	0.064 (2)	0.049 (2)	0.063 (2)	−0.007 (1)	0.014 (1)	−0.001 (1)
C15	0.071 (2)	0.092 (2)	0.109 (2)	−0.006 (2)	0.040 (2)	−0.016 (2)
C16	0.060 (2)	0.072 (2)	0.088 (2)	−0.009 (1)	0.013 (1)	−0.000 (2)

Geometric parameters (Å, º)

S1—O1	1.435 (2)	C12—C13	1.396 (3)
S1—O2	1.426 (2)	C13—C14	1.365 (4)
S1—N1	1.645 (2)	C1—H1	0.960
S1—C5	1.755 (2)	C1—H2	0.960
N1—C8	1.289 (4)	C1—H3	0.960
N2—C12	1.355 (4)	C3—H4	0.980
N2—C15	1.447 (4)	C4—H5	0.980
N2—C16	1.435 (3)	C6—H6	0.980
C1—C2	1.501 (4)	C7—H7	0.980
C2—C3	1.375 (4)	C8—H8	0.980
C2—C7	1.381 (4)	C10—H9	0.980
C3—C4	1.386 (4)	C11—H10	0.980
C4—C5	1.368 (3)	C13—H11	0.980
C5—C6	1.371 (4)	C14—H12	0.980
C6—C7	1.380 (4)	C15—H13	0.960
C8—C9	1.432 (4)	C15—H14	0.960
C9—C10	1.388 (3)	C15—H15	0.960
C9—C14	1.398 (4)	C16—H16	0.960
C10—C11	1.364 (4)	C16—H17	0.960
C11—C12	1.420 (4)	C16—H18	0.960
S1···C4	2.710 (3)	C3···C5	2.372 (4)
S1···C6	2.711 (3)	C3···C6	2.729 (4)
S1···C8	2.513 (3)	C3···C7	2.367 (4)
O1···O2	2.460 (3)	C4···C6	2.375 (4)
O1···N1	2.559 (3)	C4···C7	2.761 (4)
O1···C4	2.926 (3)	C5···C7	2.389 (4)
O1···C5	2.594 (3)	C5···C8	3.396 (4)
O1···C8	2.810 (4)	C6···C1^iv	3.581 (5)
O1···C16^i	3.238 (3)	C8···O2^v	3.557 (3)
O2···N1	2.450 (3)	C8···C10	2.469 (4)
O2···C5	2.596 (3)	C8···C14	2.452 (4)
O2···C6	2.997 (3)	C9···C11	2.405 (3)
O2···C8	3.568 (4)	C9···C12	2.818 (4)
O2···C8^ii	3.557 (3)	C9···C13	2.409 (4)
N1···C4	3.504 (3)	C10···C12	2.418 (4)
N1···C5	2.635 (3)	C10···C13	2.753 (4)
N1···C6	3.289 (4)	C10···C14	2.384 (3)
N1···C9	2.388 (4)	C11···C13	2.405 (3)
N1···C10	2.868 (3)	C11···C14	2.758 (3)
N2···C11	2.411 (4)	C11···C16	2.823 (4)
N2···C13	2.408 (3)	C12···C14	2.407 (3)
C1···C3	2.497 (5)	C12···C15	2.440 (5)
C1···C6^iii	3.581 (5)	C12···C16	2.432 (4)
C1···C7	2.510 (4)	C13···C15	2.845 (4)
C2···C4	2.411 (4)	C15···C16	2.466 (4)
C2···C5	2.770 (4)	C16···O1^vi	3.238 (3)
C2···C6	2.393 (4)
O2—S1—O1	118.6 (1)	N2—C15—H15	109.6
N1—S1—O1	112.2 (1)	N2—C16—H16	109.6
C5—S1—O1	108.4 (1)	N2—C16—H17	109.3
N1—S1—O2	105.6 (1)	N2—C16—H18	109.5
C5—S1—O2	109.0 (1)	H1—C1—C2	108.9
C5—S1—N1	101.6 (1)	H2—C1—C2	109.3
S1—N1—C8	117.3 (2)	H3—C1—C2	109.9
S1—C5—C4	119.9 (2)	H2—C1—H1	109.5
S1—C5—C6	119.8 (2)	H3—C1—H1	109.4
N1—C8—C9	122.6 (2)	H3—C1—H2	109.8
N2—C12—C11	120.6 (2)	C2—C3—H4	119.2
N2—C12—C13	122.2 (2)	C2—C7—H7	119.6
C15—N2—C12	121.0 (2)	C3—C4—H5	120.7
C16—N2—C12	121.3 (2)	H4—C3—C4	119.0
C16—N2—C15	117.6 (2)	H5—C4—C5	120.3
C1—C2—C3	120.5 (2)	C5—C6—H6	119.6
C1—C2—C7	121.1 (3)	H6—C6—C7	119.8
C2—C3—C4	121.7 (3)	C6—C7—H7	120.2
C7—C2—C3	118.4 (3)	H8—C8—C9	118.6
C2—C7—C6	120.2 (3)	C9—C10—H9	119.3
C3—C4—C5	118.9 (3)	C9—C14—H12	119.5
C4—C5—C6	120.2 (2)	H9—C10—C11	118.9
C5—C6—C7	120.5 (2)	C10—C11—H10	120.0
C8—C9—C10	122.2 (2)	H10—C11—C12	119.5
C8—C9—C14	120.1 (2)	C12—C13—H11	119.1
C9—C10—C11	121.8 (2)	H11—C13—C14	119.6
C14—C9—C10	117.7 (2)	C13—C14—H12	119.2
C9—C14—C13	121.3 (2)	H14—C15—H13	109.6
C10—C11—C12	120.5 (2)	H15—C15—H13	109.5
C11—C12—C13	117.2 (2)	H15—C15—H14	109.2
C12—C13—C14	121.4 (3)	H17—C16—H16	109.5
N1—C8—H8	118.8	H18—C16—H16	109.5
N2—C15—H13	109.2	H18—C16—H17	109.5
N2—C15—H14	109.7
O1—S1—N1—C8	17.4 (2)	C2—C3—C4—C5	0.6 (5)
O2—S1—N1—C8	148.0 (2)	C3—C4—C5—S1	−177.9 (2)
C5—S1—N1—C8	−98.2 (2)	C3—C4—C5—C6	−1.4 (4)
O1—S1—C5—C4	−19.1 (3)	S1—C5—C6—C7	177.4 (3)
O1—S1—C5—C6	164.4 (2)	C4—C5—C6—C7	0.9 (4)
O2—S1—C5—C4	−149.5 (2)	C5—C6—C7—C2	0.5 (5)
O2—S1—C5—C6	34.0 (3)	N1—C8—C9—C10	−0.7 (4)
N1—S1—C5—C4	99.3 (2)	N1—C8—C9—C14	179.2 (2)
N1—S1—C5—C6	−77.2 (2)	C8—C9—C10—C11	179.8 (2)
S1—N1—C8—C9	179.8 (2)	C14—C9—C10—C11	−0.2 (4)
C15—N2—C12—C11	−177.8 (2)	C8—C9—C14—C13	−178.8 (2)
C15—N2—C12—C13	1.9 (4)	C10—C9—C14—C13	1.1 (4)
C16—N2—C12—C11	−0.3 (3)	C9—C10—C11—C12	−0.8 (4)
C16—N2—C12—C13	179.5 (2)	C10—C11—C12—N2	−179.4 (2)
C1—C2—C3—C4	−179.0 (3)	C10—C11—C12—C13	0.9 (3)
C7—C2—C3—C4	0.8 (5)	N2—C12—C13—C14	−179.7 (2)
C1—C2—C7—C6	178.4 (3)	C11—C12—C13—C14	0.0 (3)
C3—C2—C7—C6	−1.4 (4)	C12—C13—C14—C9	−1.0 (4)

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