N-(N-Phenyl­benzimido­yl)thio­benzanilide

The oxidation of thio­benzanilide by lead(IV) tetra­acetate yields bis­(N-phenyl­benzimido­yl) disulfide and N-(N-phenyl­benzimido­yl)thio­benzanilide, C₂₆H₂₀N₂S. The latter mol­ecule consists of a PhN=C(Ph)- fragment that is linked to a PhC(S)-N(Ph)- fragment by a C-N single bond [1.410 (3) Å]. The two fragements are aligned at approximately 90° to one another.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.153
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     -   C25     ..       7.26 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8     -   C9      ..      10.74 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C11    -   C12     ..       8.25 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C19    -   C24     ..       9.23 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.78 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       6.95 su

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3659
           From the CIF: _diffrn_reflns_limit_ max hkl   11.   23.   13.
           From the CIF: _diffrn_reflns_limit_ min hkl   -9.  -21.  -13.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   13.   23.   11.
           Calculated minimum hkl  -13.  -23.  -11.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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

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Computing details

Data collection: SMART (Bruker, 1995); cell refinement: SAINT (Bruker, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N-(N-Phenylbenzimidoyl)thiobenzanilide

Crystal data

C26H20N2S	F(000) = 824
Mr = 392.50	Dx = 1.252 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 750 reflections
a = 11.0162 (12) Å	θ = 2.8–19.2°
b = 19.980 (2) Å	µ = 0.17 mm^−1
c = 9.5802 (10) Å	T = 295 K
β = 99.092 (3)°	Block, yellow
V = 2082.1 (4) Å^3	0.2 × 0.1 × 0.1 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −9→11
12173 measured reflections	k = −21→23
3659 independent reflections	l = −13→13

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.3122P] where P = (Fo^2 + 2Fc^2)/3
3659 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.31238 (8)	0.34143 (4)	0.41931 (8)	0.0516 (3)
N1	0.2697 (2)	0.4019 (1)	0.1738 (2)	0.036 (1)
N2	0.0605 (2)	0.4295 (1)	0.1868 (2)	0.045 (1)
C1	0.4567 (2)	0.3336 (1)	0.2126 (2)	0.040 (1)
C2	0.4931 (2)	0.2687 (1)	0.2508 (2)	0.052 (1)
C3	0.5984 (2)	0.2422 (1)	0.2094 (2)	0.069 (1)
C4	0.6674 (2)	0.2806 (1)	0.1297 (2)	0.071 (1)
C5	0.6311 (2)	0.3455 (1)	0.0915 (2)	0.066 (1)
C6	0.5257 (2)	0.3721 (1)	0.1330 (2)	0.053 (1)
C7	0.2652 (2)	0.4076 (1)	0.0241 (1)	0.039 (1)
C8	0.2593 (2)	0.4713 (1)	−0.0350 (2)	0.054 (1)
C9	0.2486 (2)	0.4789 (1)	−0.1806 (2)	0.074 (1)
C10	0.2437 (2)	0.4228 (1)	−0.2672 (1)	0.076 (1)
C11	0.2496 (2)	0.3591 (1)	−0.2081 (2)	0.063 (1)
C12	0.2603 (2)	0.3515 (1)	−0.0625 (2)	0.046 (1)
C13	0.0191 (2)	0.3754 (1)	0.0973 (2)	0.043 (1)
C14	−0.0479 (2)	0.3886 (1)	−0.0353 (2)	0.052 (1)
C15	−0.0939 (2)	0.3361 (1)	−0.1232 (2)	0.057 (1)
C16	−0.0729 (2)	0.2703 (1)	−0.0785 (2)	0.059 (1)
C17	−0.0059 (2)	0.2571 (1)	0.0541 (2)	0.057 (1)
C18	0.04007 (2)	0.3096 (1)	0.1420 (2)	0.049 (1)
C19	0.21461 (2)	0.4950 (1)	0.3284 (2)	0.041 (1)
C20	0.12760 (2)	0.5252 (1)	0.3982 (2)	0.052 (1)
C21	0.1610 (2)	0.5786 (1)	0.4890 (2)	0.065 (1)
C22	0.2814 (2)	0.6020 (1)	0.5099 (2)	0.072 (1)
C23	0.3684 (2)	0.5718 (1)	0.4401 (2)	0.071 (1)
C24	0.3350 (2)	0.5183 (1)	0.3493 (2)	0.056 (1)
C25	0.3444 (3)	0.3601 (1)	0.2606 (3)	0.039 (1)
C26	0.1743 (3)	0.4391 (1)	0.2300 (3)	0.039 (1)
H2	0.4469	0.2430	0.3041	0.062*
H3	0.6228	0.1987	0.2349	0.083*
H4	0.7380	0.2628	0.1020	0.085*
H5	0.6772	0.3712	0.0383	0.079*
H6	0.5013	0.4155	0.1074	0.063*
H8	0.2626	0.5088	0.0229	0.065*
H9	0.2447	0.5215	−0.2202	0.089*
H10	0.2366	0.4279	−0.3647	0.091*
H11	0.2463	0.3216	−0.2660	0.075*
H12	0.2642	0.3089	−0.0229	0.056*
H14	−0.0619	0.4326	−0.0652	0.062*
H15	−0.1387	0.3450	−0.2119	0.069*
H16	−0.1036	0.2352	−0.1373	0.071*
H17	0.0082	0.2131	0.0840	0.069*
H18	0.0849	0.3008	0.2308	0.059*
H20	0.0471	0.5095	0.3842	0.063*
H21	0.1028	0.5988	0.5357	0.078*
H22	0.3037	0.6378	0.5707	0.086*
H23	0.4489	0.5874	0.4541	0.085*
H24	0.3932	0.4981	0.3026	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0397 (5)	0.0533 (5)	0.0625 (5)	−0.0067 (4)	0.0106 (4)	−0.0053 (4)
N1	0.032 (1)	0.036 (1)	0.041 (1)	0.003 (1)	0.007 (1)	−0.005 (1)
N2	0.045 (2)	0.048 (2)	0.041 (2)	0.008 (1)	0.005 (1)	−0.003 (1)
C1	0.040 (2)	0.043 (2)	0.037 (2)	0.005 (1)	0.002 (1)	−0.002 (1)
C2	0.059 (2)	0.047 (2)	0.049 (2)	0.001 (2)	0.005 (2)	−0.007 (2)
C3	0.087 (3)	0.058 (2)	0.061 (2)	0.007 (2)	0.008 (2)	−0.021 (2)
C4	0.069 (2)	0.095 (3)	0.049 (2)	0.014 (2)	0.010 (2)	−0.018 (2)
C5	0.061 (2)	0.089 (3)	0.048 (2)	−0.001 (2)	0.015 (2)	0.004 (2)
C6	0.054 (2)	0.060 (2)	0.045 (2)	−0.004 (2)	0.009 (2)	0.000 (2)
C7	0.035 (2)	0.042 (2)	0.040 (2)	−0.001 (1)	0.006 (1)	−0.005 (1)
C8	0.042 (2)	0.048 (2)	0.074 (2)	−0.004 (2)	0.015 (2)	−0.008 (2)
C9	0.052 (2)	0.066 (3)	0.107 (3)	−0.022 (2)	0.019 (2)	−0.021 (2)
C10	0.037 (2)	0.087 (3)	0.105 (3)	−0.005 (2)	0.015 (2)	−0.026 (3)
C11	0.041 (2)	0.076 (3)	0.070 (2)	0.011 (2)	0.006 (2)	−0.018 (2)
C12	0.044 (2)	0.048 (2)	0.047 (2)	0.002 (2)	0.006 (1)	−0.009 (2)
C13	0.044 (2)	0.053 (2)	0.035 (2)	0.008 (2)	0.011 (1)	0.002 (1)
C14	0.049 (2)	0.058 (2)	0.047 (2)	0.000 (2)	0.002 (2)	−0.004 (2)
C15	0.043 (2)	0.076 (3)	0.050 (2)	0.004 (2)	−0.001 (2)	0.008 (2)
C16	0.053 (2)	0.067 (3)	0.057 (2)	0.014 (2)	0.010 (2)	0.017 (2)
C17	0.064 (2)	0.049 (2)	0.059 (2)	0.001 (2)	0.011 (2)	0.013 (2)
C18	0.042 (2)	0.059 (2)	0.045 (2)	−0.001 (2)	0.003 (1)	0.008 (2)
C19	0.035 (2)	0.034 (2)	0.053 (2)	0.000 (1)	0.003 (1)	−0.002 (1)
C20	0.041 (2)	0.046 (2)	0.070 (2)	0.001 (2)	0.011 (2)	−0.006 (2)
C21	0.047 (2)	0.042 (2)	0.105 (3)	0.004 (2)	0.009 (2)	−0.020 (2)
C22	0.048 (2)	0.043 (2)	0.113 (3)	0.009 (2)	−0.019 (2)	0.001 (2)
C23	0.075 (3)	0.055 (2)	0.075 (3)	0.003 (2)	−0.015 (2)	0.009 (2)
C24	0.058 (2)	0.048 (2)	0.058 (2)	0.006 (2)	0.001 (2)	0.003 (2)
C25	0.040 (2)	0.034 (2)	0.041 (2)	0.002 (1)	0.000 (1)	0.002 (1)
C26	0.035 (2)	0.037 (2)	0.046 (2)	−0.002 (1)	0.008 (1)	−0.004 (1)

Geometric parameters (Å, º)

S1—C25	1.656 (3)	C19—C24	1.39
N1—C25	1.361 (3)	C19—C26	1.483 (3)
N1—C7	1.431 (2)	C20—C21	1.39
N1—C26	1.458 (3)	C21—C22	1.39
N2—C26	1.271 (3)	C22—C23	1.39
N2—C13	1.410 (3)	C23—C24	1.39
C1—C2	1.39	C2—H2	0.93
C1—C6	1.39	C3—H3	0.93
C1—C25	1.483 (3)	C4—H4	0.93
C2—C3	1.39	C5—H5	0.93
C3—C4	1.39	C6—H6	0.93
C4—C5	1.39	C8—H8	0.93
C5—C6	1.39	C9—H9	0.93
C7—C8	1.39	C10—H10	0.93
C7—C12	1.39	C11—H11	0.93
C8—C9	1.39	C12—H12	0.93
C9—C10	1.39	C14—H14	0.93
C10—C11	1.39	C15—H15	0.93
C11—C12	1.39	C16—H16	0.93
C13—C14	1.39	C17—H17	0.93
C13—C18	1.39	C18—H18	0.93
C14—C15	1.39	C20—H20	0.93
C15—C16	1.39	C21—H21	0.93
C16—C17	1.39	C22—H22	0.93
C17—C18	1.39	C23—H23	0.93
C19—C20	1.39	C24—H24	0.93
C25—N1—C7	125.7 (2)	N1—C26—C19	117.2 (2)
C25—N1—C26	119.3 (2)	C3—C2—H2	120.0
C7—N1—C26	114.6 (2)	C1—C2—H2	120.0
C26—N2—C13	121.4 (2)	C2—C3—H3	120.0
C2—C1—C6	120.0	C4—C3—H3	120.0
C2—C1—C25	118.1 (2)	C5—C4—H4	120.0
C6—C1—C25	121.9 (2)	C3—C4—H4	120.0
C3—C2—C1	120.0	C4—C5—H5	120.0
C2—C3—C4	120.0	C6—C5—H5	120.0
C5—C4—C3	120.0	C5—C6—H6	120.0
C4—C5—C6	120.0	C1—C6—H6	120.0
C5—C6—C1	120.0	C9—C8—H8	120.0
C8—C7—C12	120.0	C7—C8—H8	120.0
C8—C7—N1	118.2 (2)	C10—C9—H9	120.0
C12—C7—N1	121.7 (2)	C8—C9—H9	120.0
C9—C8—C7	120.0	C9—C10—H10	120.0
C10—C9—C8	120.0	C11—C10—H10	120.0
C9—C10—C11	120.0	C12—C11—H11	120.0
C12—C11—C10	120.0	C10—C11—H11	120.0
C11—C12—C7	120.0	C11—C12—H12	120.0
C14—C13—C18	120.0	C7—C12—H12	120.0
C14—C13—N2	118.9 (2)	C13—C14—H14	120.0
C18—C13—N2	121.0 (2)	C15—C14—H14	120.0
C13—C14—C15	120.0	C16—C15—H15	120.0
C16—C15—C14	120.0	C14—C15—H15	120.0
C15—C16—C17	120.0	C15—C16—H16	120.0
C16—C17—C18	120.0	C17—C16—H16	120.0
C17—C18—C13	120.0	C16—C17—H17	120.0
C20—C19—C24	120.0	C18—C17—H17	120.0
C20—C19—C26	118.2 (2)	C17—C18—H18	120.0
C24—C19—C26	121.8 (2)	C13—C18—H18	120.0
C19—C20—C21	120.0	C19—C20—H20	120.0
C22—C21—C20	120.0	C21—C20—H20	120.0
C23—C22—C21	120.0	C22—C21—H21	120.0
C22—C23—C24	120.0	C20—C21—H21	120.0
C23—C24—C19	120.0	C23—C22—H22	120.0
N1—C25—C1	118.9 (2)	C21—C22—H22	120.0
N1—C25—S1	120.2 (2)	C22—C23—H23	120.0
C1—C25—S1	120.9 (2)	C24—C23—H23	120.0
N2—C26—N1	122.3 (3)	C23—C24—H24	120.0
N2—C26—C19	120.1 (2)	C19—C24—H24	120.0
C25—C1—C2—C3	−179.3 (2)	C7—N1—C25—S1	−161.3 (2)
C25—C1—C6—C5	179.3 (2)	C26—N1—C25—S1	10.6 (3)
C25—N1—C7—C8	−136.6 (2)	C2—C1—C25—N1	−144.4 (2)
C26—N1—C7—C8	51.1 (3)	C6—C1—C25—N1	36.3 (3)
C25—N1—C7—C12	46.7 (3)	C2—C1—C25—S1	37.7 (3)
C26—N1—C7—C12	−125.6 (2)	C6—C1—C25—S1	−141.6 (2)
N1—C7—C8—C9	−176.8 (2)	C13—N2—C26—N1	9.7 (4)
N1—C7—C12—C11	176.7 (2)	C13—N2—C26—C19	−177.6 (2)
C26—N2—C13—C14	−119.7 (2)	C25—N1—C26—N2	−115.3 (3)
C26—N2—C13—C18	62.8 (3)	C7—N1—C26—N2	57.5 (3)
N2—C13—C14—C15	−177.5 (2)	C25—N1—C26—C19	71.8 (3)
N2—C13—C18—C17	177.4 (2)	C7—N1—C26—C19	−115.4 (2)
C26—C19—C20—C21	−178.6 (2)	C20—C19—C26—N2	15.7 (3)
C26—C19—C24—C23	178.5 (2)	C24—C19—C26—N2	−162.9 (2)
C7—N1—C25—C1	20.8 (4)	C20—C19—C26—N1	−171.3 (2)
C26—N1—C25—C1	−167.2 (2)	C24—C19—C26—N1	10.1 (3)