N,N-Dibenzyl-3-nitro­benzene­sulfenamide

In the title mol­ecule, C₂₀H₁₈N₂O₂S, all bond lengths and angles are within normal ranges. Weak inter­molecular C—H...O inter­actions link the mol­ecules into centrosymmetric dimers. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.174
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N-Dibenzyl-3-nitrobenzenesulfenamide

Crystal data

C20H18N2O2S	F(000) = 736
Mr = 350.42	Dx = 1.317 Mg m^−3
Monoclinic, P21/c	Melting point: 358 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.599 (2) Å	Cell parameters from 4503 reflections
b = 20.30 (2) Å	θ = 1.7–27.0°
c = 15.557 (6) Å	µ = 0.20 mm^−1
β = 90.585 (12)°	T = 298 K
V = 1768 (2) Å^3	Prism, yellow
Z = 4	0.35 × 0.23 × 0.19 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3955 independent reflections
Radiation source: fine-focus sealed tube	3247 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −7→7
Tmin = 0.943, Tmax = 0.960	k = −26→24
9951 measured reflections	l = −20→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.059	w = 1/[σ^2(Fo^2) + (0.0751P)^2 + 0.4961P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.174	(Δ/σ)max < 0.001
S = 1.19	Δρmax = 0.31 e Å^−3
3955 reflections	Δρmin = −0.27 e Å^−3
227 parameters

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = 0.49156(0.00099) m2 = -0.85909(0.00060) m3 = -0.14258(0.00112) D = -2.52452(0.01502) Atom d s d/s (d/s)**2 C1 * -0.0025 0.0021 - 1.167 1.362 C2 * 0.0014 0.0027 0.529 0.280 C3 * 0.0023 0.0029 0.802 0.642 C4 * -0.0034 0.0029 - 1.183 1.400 C5 * 0.0004 0.0029 0.157 0.025 C6 * 0.0030 0.0027 1.118 1.249 ============ Sum((d/s)**2) for starred atoms 4.958 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate significantly from planarity

Plane 2 m1 = 0.48662(0.00096) m2 = -0.00592(0.00095) m3 = -0.87359(0.00054) D = -8.70554(0.01001) Atom d s d/s (d/s)**2 C9 * 0.0011 0.0020 0.543 0.295 C10 * -0.0030 0.0024 - 1.215 1.476 C11 * 0.0012 0.0026 0.450 0.203 C12 * 0.0026 0.0026 0.998 0.997 C13 * -0.0041 0.0026 - 1.586 2.516 C14 * 0.0015 0.0023 0.653 0.427 ============ Sum((d/s)**2) for starred atoms 5.914 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate significantly from planarity

Plane 3 m1 = 0.61344(0.00073) m2 = 0.07968(0.00096) m3 = -0.78571(0.00056) D = -4.60722(0.00549) Atom d s d/s (d/s)**2 C15 * -0.0073 0.0021 - 3.521 12.400 C16 * 0.0026 0.0025 1.064 1.133 C17 * 0.0075 0.0027 2.731 7.457 C18 * -0.0067 0.0024 - 2.774 7.694 C19 * -0.0006 0.0023 - 0.279 0.078 C20 * 0.0075 0.0022 3.396 11.531 ============ Sum((d/s)**2) for starred atoms 40.293 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 4 m1 = -0.59144(0.00152) m2 = -0.07604(0.00542) m3 = 0.80275(0.00137) D = 4.71382(0.00988) Atom d s d/s (d/s)**2 N2 * 0.0000 0.0024 0.000 0.000 O2 * 0.0000 0.0028 0.000 0.000 O1 * 0.0000 0.0028 0.000 0.000 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 5 m1 = 0.68304(0.00075) m2 = 0.41302(0.00123) m3 = 0.60239(0.00063) D = 9.16407(0.00419) Atom d s d/s (d/s)**2 S1 * 0.0000 0.0007 0.000 0.000 C8 * 0.0000 0.0023 0.000 0.000 C7 * 0.0000 0.0025 0.000 0.000 N1 0.3931 0.0018 221.067 48870.707 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 6 m1 = -0.35327(0.00238) m2 = -0.21906(0.00183) m3 = -0.90951(0.00123) D = -11.15265(0.00405) Atom d s d/s (d/s)**2 C8 * 0.0000 0.0023 0.000 0.000 N1 * 0.0000 0.0017 0.000 0.000 C7 * 0.0000 0.0024 0.000 0.000 ============ Sum((d/s)**2) for starred atoms 0.000

Plane 7 m1 = 0.44301(0.00147) m2 = -0.89633(0.00073) m3 = -0.01807(0.00102) D = -2.66350(0.01138) Atom d s d/s (d/s)**2 C15 * 0.0000 0.0025 0.000 0.000 S1 * 0.0000 0.0009 0.000 0.000 N1 * 0.0000 0.0019 0.000 0.000 ============ Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 68.36 (0.08) 111.64 (0.08) 1 3 69.81 (0.08) 110.19 (0.08) 1 4 70.13 (0.30) 109.87 (0.30) 1 5 83.97 (0.09) 96.03 (0.09) 1 6 81.71 (0.13) 98.29 (0.13) 1 7 7.96 (0.09) 172.04 (0.09) 2 3 10.12 (0.07) 169.88 (0.07) 2 4 8.65 (0.18) 171.35 (0.18) 2 5 78.68 (0.06) 101.32 (0.06) 2 6 51.40 (0.13) 128.60 (0.13) 2 7 76.31 (0.08) 103.69 (0.08) 3 4 1.61 (0.10) 178.39 (0.10) 3 5 88.77 (0.05) 91.23 (0.05) 3 6 61.28 (0.13) 118.72 (0.13) 3 7 77.61 (0.09) 102.39 (0.09) 4 5 87.24 (0.16) 92.76 (0.16) 4 6 59.70 (0.18) 120.30 (0.18) 4 7 77.97 (0.30) 102.03 (0.30) 5 6 28.40 (0.13) 151.60 (0.13) 5 7 85.50 (0.09) 94.50 (0.09) 6 7 86.77 (0.13) 93.23 (0.13)

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
S1	0.56277 (10)	0.21224 (3)	0.56495 (4)	0.0405 (2)
O1	0.2354 (5)	−0.01340 (11)	0.43497 (18)	0.0866 (8)
O2	−0.0683 (5)	0.00805 (12)	0.35767 (17)	0.0968 (9)
N1	0.4582 (3)	0.19604 (9)	0.66524 (11)	0.0333 (4)
N2	0.0969 (5)	0.02535 (12)	0.40327 (14)	0.0561 (6)
C1	0.4650 (4)	0.11507 (10)	0.78420 (14)	0.0352 (5)
C2	0.2882 (4)	0.08128 (13)	0.82716 (17)	0.0470 (6)
H2	0.1582	0.0647	0.7964	0.0584 (19)*
C3	0.3016 (5)	0.07175 (14)	0.91512 (18)	0.0550 (7)
H3	0.1811	0.0488	0.9429	0.0584 (19)*
C4	0.4923 (5)	0.09605 (14)	0.96164 (17)	0.0542 (7)
H4	0.5007	0.09	1.0208	0.0584 (19)*
C5	0.6703 (5)	0.12944 (14)	0.91983 (17)	0.0534 (7)
H5	0.8002	0.1458	0.9509	0.0584 (19)*
C6	0.6573 (4)	0.13881 (13)	0.83204 (16)	0.0465 (6)
H6	0.7792	0.1614	0.8045	0.0584 (19)*
C7	0.4559 (5)	0.12508 (11)	0.68794 (15)	0.0418 (6)
H7A	0.5921	0.1035	0.6621	0.0584 (19)*
H7B	0.3121	0.1049	0.6648	0.0584 (19)*
C8	0.2318 (4)	0.22871 (11)	0.68671 (15)	0.0373 (5)
H8A	0.1861	0.2157	0.7442	0.0584 (19)*
H8B	0.1084	0.2134	0.6473	0.0584 (19)*
C9	0.2428 (4)	0.30316 (11)	0.68264 (13)	0.0325 (5)
C10	0.4294 (4)	0.33820 (12)	0.71981 (16)	0.0427 (6)
H10	0.5554	0.3155	0.7456	0.0584 (19)*
C11	0.4314 (4)	0.40637 (13)	0.71931 (17)	0.0480 (6)
H11	0.5587	0.429	0.7444	0.0584 (19)*
C12	0.2455 (4)	0.44107 (13)	0.68185 (17)	0.0474 (6)
H12	0.2472	0.4869	0.6814	0.0584 (19)*
C13	0.0578 (4)	0.40712 (13)	0.64521 (17)	0.0496 (6)
H13	−0.069	0.4301	0.6204	0.0584 (19)*
C14	0.0568 (4)	0.33870 (12)	0.64521 (15)	0.0414 (5)
H14	−0.0704	0.3163	0.6198	0.0584 (19)*
C15	0.3364 (4)	0.18277 (12)	0.49231 (13)	0.0352 (5)
C16	0.1797 (5)	0.22795 (12)	0.45375 (15)	0.0452 (6)
H16	0.1979	0.2728	0.4645	0.0584 (19)*
C17	−0.0016 (5)	0.20647 (14)	0.40001 (17)	0.0524 (7)
H17	−0.104	0.2369	0.3744	0.0584 (19)*
C18	−0.0319 (5)	0.14010 (14)	0.38399 (15)	0.0484 (6)
H18	−0.1556	0.1252	0.3486	0.0584 (19)*
C19	0.1262 (4)	0.09632 (12)	0.42182 (14)	0.0397 (5)
C20	0.3110 (4)	0.11585 (11)	0.47526 (14)	0.0378 (5)
H20	0.4157	0.0852	0.4992	0.0584 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0431 (3)	0.0446 (4)	0.0339 (3)	−0.0127 (2)	0.0018 (2)	−0.0058 (2)
O1	0.1130 (19)	0.0411 (13)	0.105 (2)	0.0119 (13)	−0.0193 (16)	−0.0235 (12)
O2	0.140 (2)	0.0680 (16)	0.0815 (17)	−0.0458 (16)	−0.0434 (16)	−0.0047 (13)
N1	0.0424 (10)	0.0281 (10)	0.0292 (9)	−0.0016 (8)	−0.0008 (7)	−0.0031 (7)
N2	0.0839 (16)	0.0445 (13)	0.0397 (12)	−0.0136 (12)	−0.0044 (11)	−0.0096 (10)
C1	0.0461 (12)	0.0232 (11)	0.0363 (12)	0.0027 (9)	−0.0037 (9)	−0.0025 (9)
C2	0.0446 (13)	0.0407 (14)	0.0554 (16)	−0.0068 (11)	−0.0061 (11)	−0.0001 (11)
C3	0.0582 (15)	0.0528 (17)	0.0544 (17)	−0.0099 (13)	0.0132 (12)	0.0077 (13)
C4	0.0733 (17)	0.0529 (17)	0.0362 (13)	0.0057 (14)	−0.0006 (12)	0.0044 (12)
C5	0.0569 (15)	0.0581 (17)	0.0449 (15)	−0.0071 (13)	−0.0155 (12)	−0.0004 (12)
C6	0.0485 (13)	0.0464 (15)	0.0445 (14)	−0.0127 (11)	−0.0015 (10)	0.0004 (11)
C7	0.0609 (14)	0.0277 (12)	0.0367 (13)	−0.0018 (10)	−0.0058 (10)	−0.0064 (9)
C8	0.0382 (11)	0.0337 (12)	0.0401 (13)	−0.0044 (9)	0.0011 (9)	−0.0008 (9)
C9	0.0353 (10)	0.0318 (12)	0.0303 (11)	−0.0008 (9)	0.0015 (8)	−0.0024 (9)
C10	0.0404 (12)	0.0410 (14)	0.0464 (14)	0.0000 (10)	−0.0114 (10)	−0.0032 (11)
C11	0.0485 (13)	0.0387 (14)	0.0567 (16)	−0.0072 (11)	−0.0064 (11)	−0.0119 (12)
C12	0.0559 (14)	0.0309 (13)	0.0555 (16)	0.0041 (11)	0.0074 (12)	−0.0020 (11)
C13	0.0477 (13)	0.0448 (15)	0.0562 (16)	0.0111 (11)	−0.0048 (11)	0.0061 (12)
C14	0.0361 (11)	0.0451 (14)	0.0430 (13)	0.0006 (10)	−0.0056 (9)	−0.0044 (11)
C15	0.0439 (11)	0.0361 (12)	0.0256 (10)	−0.0052 (10)	0.0015 (8)	−0.0021 (9)
C16	0.0657 (15)	0.0330 (13)	0.0367 (13)	0.0012 (11)	0.0001 (11)	0.0008 (10)
C17	0.0650 (16)	0.0515 (17)	0.0405 (14)	0.0121 (13)	−0.0121 (12)	0.0041 (12)
C18	0.0549 (14)	0.0568 (17)	0.0333 (13)	−0.0038 (12)	−0.0105 (10)	−0.0001 (11)
C19	0.0569 (13)	0.0355 (13)	0.0268 (11)	−0.0074 (10)	0.0006 (9)	−0.0038 (9)
C20	0.0487 (12)	0.0347 (12)	0.0297 (11)	0.0037 (10)	−0.0034 (9)	−0.0025 (9)

Geometric parameters (Å, º)

S1—N1	1.7042 (19)	C8—H8B	0.97
S1—C15	1.792 (2)	C9—C10	1.385 (3)
O1—N2	1.206 (3)	C9—C14	1.390 (3)
O2—N2	1.212 (3)	C10—C11	1.383 (4)
N1—C8	1.472 (3)	C10—H10	0.93
N1—C7	1.483 (3)	C11—C12	1.381 (4)
N2—C19	1.478 (3)	C11—H11	0.93
C1—C2	1.382 (3)	C12—C13	1.376 (4)
C1—C6	1.389 (3)	C12—H12	0.93
C1—C7	1.512 (3)	C13—C14	1.389 (4)
C2—C3	1.383 (4)	C13—H13	0.93
C2—H2	0.93	C14—H14	0.93
C3—C4	1.375 (4)	C15—C20	1.391 (3)
C3—H3	0.93	C15—C16	1.400 (3)
C4—C5	1.374 (4)	C16—C17	1.379 (4)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.380 (4)	C17—C18	1.380 (4)
C5—H5	0.93	C17—H17	0.93
C6—H6	0.93	C18—C19	1.381 (3)
C7—H7A	0.97	C18—H18	0.93
C7—H7B	0.97	C19—C20	1.379 (3)
C8—C9	1.513 (3)	C20—H20	0.93
C8—H8A	0.97
N1—S1—C15	105.39 (10)	C10—C9—C14	117.8 (2)
C8—N1—C7	111.97 (18)	C10—C9—C8	121.7 (2)
C8—N1—S1	115.19 (15)	C14—C9—C8	120.3 (2)
C7—N1—S1	114.16 (14)	C11—C10—C9	121.2 (2)
O1—N2—O2	122.3 (3)	C11—C10—H10	119.4
O1—N2—C19	119.1 (2)	C9—C10—H10	119.4
O2—N2—C19	118.6 (3)	C12—C11—C10	120.4 (2)
C2—C1—C6	117.9 (2)	C12—C11—H11	119.8
C2—C1—C7	121.9 (2)	C10—C11—H11	119.8
C6—C1—C7	120.2 (2)	C13—C12—C11	119.3 (2)
C1—C2—C3	121.1 (2)	C13—C12—H12	120.4
C1—C2—H2	119.5	C11—C12—H12	120.4
C3—C2—H2	119.5	C12—C13—C14	120.2 (2)
C4—C3—C2	120.3 (2)	C12—C13—H13	119.9
C4—C3—H3	119.9	C14—C13—H13	119.9
C2—C3—H3	119.9	C13—C14—C9	121.1 (2)
C5—C4—C3	119.4 (2)	C13—C14—H14	119.5
C5—C4—H4	120.3	C9—C14—H14	119.5
C3—C4—H4	120.3	C20—C15—C16	119.7 (2)
C4—C5—C6	120.3 (2)	C20—C15—S1	121.08 (17)
C4—C5—H5	119.8	C16—C15—S1	119.19 (19)
C6—C5—H5	119.8	C17—C16—C15	120.5 (2)
C5—C6—C1	121.0 (2)	C17—C16—H16	119.8
C5—C6—H6	119.5	C15—C16—H16	119.8
C1—C6—H6	119.5	C16—C17—C18	120.4 (2)
N1—C7—C1	111.48 (17)	C16—C17—H17	119.8
N1—C7—H7A	109.3	C18—C17—H17	119.8
C1—C7—H7A	109.3	C17—C18—C19	118.3 (2)
N1—C7—H7B	109.3	C17—C18—H18	120.9
C1—C7—H7B	109.3	C19—C18—H18	120.9
H7A—C7—H7B	108	C20—C19—C18	123.1 (2)
N1—C8—C9	113.86 (18)	C20—C19—N2	118.6 (2)
N1—C8—H8A	108.8	C18—C19—N2	118.3 (2)
C9—C8—H8A	108.8	C19—C20—C15	118.0 (2)
N1—C8—H8B	108.8	C19—C20—H20	121
C9—C8—H8B	108.8	C15—C20—H20	121
H8A—C8—H8B	107.7
C15—S1—N1—C8	−60.87 (18)	C10—C11—C12—C13	0.2 (4)
C15—S1—N1—C7	70.74 (17)	C11—C12—C13—C14	−0.7 (4)
C6—C1—C2—C3	0.4 (4)	C12—C13—C14—C9	0.6 (4)
C7—C1—C2—C3	179.0 (2)	C10—C9—C14—C13	−0.1 (3)
C1—C2—C3—C4	0.1 (4)	C8—C9—C14—C13	176.4 (2)
C2—C3—C4—C5	−0.5 (4)	N1—S1—C15—C20	−77.0 (2)
C3—C4—C5—C6	0.3 (4)	N1—S1—C15—C16	101.62 (19)
C4—C5—C6—C1	0.2 (4)	C20—C15—C16—C17	0.9 (4)
C2—C1—C6—C5	−0.6 (4)	S1—C15—C16—C17	−177.7 (2)
C7—C1—C6—C5	−179.2 (2)	C15—C16—C17—C18	0.5 (4)
C8—N1—C7—C1	−71.0 (2)	C16—C17—C18—C19	−1.2 (4)
S1—N1—C7—C1	155.84 (16)	C17—C18—C19—C20	0.6 (4)
C2—C1—C7—N1	121.4 (2)	C17—C18—C19—N2	−178.7 (2)
C6—C1—C7—N1	−60.1 (3)	O1—N2—C19—C20	−0.3 (4)
C7—N1—C8—C9	167.67 (18)	O2—N2—C19—C20	178.6 (3)
S1—N1—C8—C9	−59.7 (2)	O1—N2—C19—C18	179.1 (3)
N1—C8—C9—C10	−46.6 (3)	O2—N2—C19—C18	−2.1 (4)
N1—C8—C9—C14	137.1 (2)	C18—C19—C20—C15	0.8 (3)
C14—C9—C10—C11	−0.4 (3)	N2—C19—C20—C15	−179.9 (2)
C8—C9—C10—C11	−176.8 (2)	C16—C15—C20—C19	−1.5 (3)
C9—C10—C11—C12	0.3 (4)	S1—C15—C20—C19	177.06 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1^i	0.97	2.57	3.443 (5)	150

Symmetry code: (i) −x+1, −y, −z+1.