Literature DB >> 21578442

Benzyl 3-(10-oxo-9,10-dihydrophenanthren-9-ylidene)dithiocarbazate.

Qiao-Ru Liu¹, Song-Mao Chu, Gan-Qing Zhao, Li-Hua Chen, Yong-Jun Han.

Abstract

In the title compound, C(22)H(16)N(2)OS(2), the phenanthrene ring is nearly perpendicular to the phenyl ring, making a dihedral angle of 87.2 (2)°. Intra-molecular N-H⋯O inter-actions are present. In the crystal structure, the mol-ecules are linked through inter-molecular C-H⋯O inter-actions. The crystal structure is also stabilized by C-H⋯π inter-actions and weak π-π contacts [centroid-centroid distance = 3.36 (6) Å].

Entities: CellLine Chemical Disease

Year: 2009 PMID： 21578442 PMCID： PMC2971360 DOI： 10.1107/S160053680904272X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological properties of Schiff bases, see: Bhandari et al. (2008 ▶). Recently, some Schiff bases derived from the reaction of S-benzyldithiocarbazate with aldehydes or ketones have been reported, see: Ali et al. (2003a ▶,b ▶); How et al. (2007 ▶); Tarafder et al. (2008 ▶); Zhou et al. (2002 ▶). For the synthesis of S-benzyldithiocarbazate, see: Chew et al. (2004 ▶). For the synthesis of the title compound, see: Ali et al. (2004 ▶).

Experimental

Crystal data

C22H16N2OS2 M = 388.49 Monoclinic, a = 14.4945 (19) Å b = 5.6978 (7) Å c = 22.816 (3) Å β = 93.610 (2)° V = 1880.6 (4) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 296 K 0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.916, T max = 0.943 9220 measured reflections 3316 independent reflections 2638 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.098 S = 1.06 3316 reflections 244 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.22 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904272X/hg2573sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680904272X/hg2573Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₂H₁₆N₂OS₂	F(000) = 808
M_r = 388.49	D_x = 1.372 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3545 reflections
a = 14.4945 (19) Å	θ = 2.2–27.1°
b = 5.6978 (7) Å	µ = 0.30 mm⁻¹
c = 22.816 (3) Å	T = 296 K
β = 93.610 (2)°	Block, brown
V = 1880.6 (4) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2638 reflections with I > 2σ(I)
graphite	R_int = 0.022
phi and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→12
T_min = 0.916, T_max = 0.943	k = −6→6
9220 measured reflections	l = −27→27

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0436P)² + 0.4502P] where P = (F_o² + 2F_c²)/3
3316 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
C1	0.12004 (12)	0.9543 (3)	0.10487 (7)	0.0410 (4)
C2	0.07744 (12)	0.7660 (3)	0.13826 (7)	0.0404 (4)
C3	0.13280 (14)	0.6058 (3)	0.17087 (8)	0.0505 (5)
H3	0.1968	0.6203	0.1718	0.061*
C4	0.09428 (15)	0.4277 (3)	0.20145 (8)	0.0570 (5)
H4	0.1320	0.3226	0.2230	0.068*
C5	−0.00057 (15)	0.4045 (3)	0.20025 (8)	0.0551 (5)
H5	−0.0269	0.2837	0.2209	0.066*
C6	−0.05593 (14)	0.5600 (3)	0.16850 (7)	0.0496 (5)
H6	−0.1198	0.5422	0.1679	0.060*
C7	−0.01904 (12)	0.7447 (3)	0.13706 (7)	0.0413 (4)
C8	−0.07862 (12)	0.9126 (3)	0.10288 (7)	0.0428 (4)
C9	−0.17451 (14)	0.8986 (4)	0.10096 (9)	0.0601 (5)
H9	−0.2023	0.7801	0.1217	0.072*
C10	−0.22943 (14)	1.0568 (4)	0.06899 (10)	0.0663 (6)
H10	−0.2934	1.0431	0.0684	0.080*
C11	−0.19058 (14)	1.2346 (4)	0.03787 (9)	0.0594 (5)
H11	−0.2279	1.3411	0.0165	0.071*
C12	−0.09620 (13)	1.2524 (3)	0.03891 (8)	0.0496 (5)
H12	−0.0693	1.3716	0.0179	0.059*
C13	−0.04017 (12)	1.0942 (3)	0.07096 (7)	0.0407 (4)
C14	0.06035 (12)	1.1237 (3)	0.07105 (7)	0.0427 (4)
C15	0.34732 (13)	1.1176 (4)	0.07602 (8)	0.0513 (5)
C16	0.51902 (14)	0.9484 (5)	0.11012 (11)	0.0836 (8)
H16A	0.5363	0.9037	0.0713	0.100*
H16B	0.5310	1.1148	0.1154	0.100*
C17	0.57478 (13)	0.8104 (4)	0.15607 (10)	0.0635 (6)
C18	0.61629 (15)	0.6028 (5)	0.14199 (11)	0.0716 (6)
H18	0.6081	0.5433	0.1041	0.086*
C19	0.67014 (17)	0.4821 (5)	0.18405 (14)	0.0816 (7)
H19	0.6984	0.3422	0.1743	0.098*
C20	0.68202 (17)	0.5671 (6)	0.23965 (13)	0.0863 (8)
H20	0.7184	0.4851	0.2677	0.104*
C21	0.64071 (19)	0.7725 (6)	0.25452 (12)	0.0867 (8)
H21	0.6489	0.8302	0.2926	0.104*
C22	0.58678 (16)	0.8938 (5)	0.21272 (12)	0.0777 (7)
H22	0.5583	1.0329	0.2229	0.093*
N1	0.20996 (10)	0.9575 (3)	0.10711 (6)	0.0466 (4)
N2	0.25374 (10)	1.1215 (3)	0.07714 (7)	0.0524 (4)
H2	0.2225	1.2296	0.0586	0.063*
O1	0.09460 (9)	1.2850 (2)	0.04354 (6)	0.0577 (4)
S1	0.39768 (3)	0.88888 (10)	0.11712 (2)	0.06204 (18)
S2	0.39996 (4)	1.31825 (12)	0.03859 (3)	0.0741 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0420 (10)	0.0423 (10)	0.0385 (9)	−0.0001 (8)	0.0004 (7)	−0.0020 (7)
C2	0.0478 (10)	0.0376 (10)	0.0356 (8)	0.0010 (8)	0.0018 (7)	−0.0025 (7)
C3	0.0527 (11)	0.0492 (11)	0.0495 (10)	0.0071 (9)	0.0025 (8)	0.0036 (9)
C4	0.0754 (15)	0.0458 (12)	0.0496 (11)	0.0112 (10)	0.0018 (10)	0.0057 (9)
C5	0.0771 (15)	0.0438 (11)	0.0445 (10)	−0.0062 (10)	0.0052 (10)	0.0042 (8)
C6	0.0570 (11)	0.0479 (11)	0.0439 (10)	−0.0082 (9)	0.0034 (8)	−0.0003 (8)
C7	0.0492 (11)	0.0387 (10)	0.0360 (8)	−0.0024 (8)	0.0016 (7)	−0.0041 (7)
C8	0.0434 (10)	0.0463 (11)	0.0386 (9)	−0.0028 (8)	0.0016 (7)	−0.0045 (8)
C9	0.0489 (12)	0.0670 (14)	0.0646 (12)	−0.0066 (10)	0.0040 (10)	0.0138 (11)
C10	0.0422 (11)	0.0809 (16)	0.0754 (14)	0.0002 (11)	0.0008 (10)	0.0102 (12)
C11	0.0511 (12)	0.0635 (13)	0.0625 (12)	0.0100 (10)	−0.0056 (9)	0.0059 (10)
C12	0.0516 (11)	0.0474 (11)	0.0491 (10)	0.0019 (9)	−0.0015 (8)	0.0040 (9)
C13	0.0439 (10)	0.0404 (10)	0.0374 (9)	−0.0004 (8)	−0.0002 (7)	−0.0031 (7)
C14	0.0489 (10)	0.0405 (10)	0.0384 (9)	−0.0010 (8)	0.0000 (7)	0.0014 (8)
C15	0.0449 (11)	0.0611 (12)	0.0479 (10)	−0.0051 (9)	0.0027 (8)	0.0007 (9)
C16	0.0429 (12)	0.112 (2)	0.0963 (17)	0.0000 (13)	0.0097 (12)	0.0408 (16)
C17	0.0373 (11)	0.0768 (16)	0.0769 (15)	−0.0056 (11)	0.0074 (10)	0.0214 (12)
C18	0.0517 (13)	0.0797 (17)	0.0837 (16)	−0.0092 (12)	0.0081 (11)	0.0086 (13)
C19	0.0622 (15)	0.0702 (16)	0.114 (2)	0.0016 (13)	0.0165 (15)	0.0235 (16)
C20	0.0586 (15)	0.099 (2)	0.100 (2)	−0.0074 (15)	−0.0065 (14)	0.0410 (18)
C21	0.0824 (18)	0.098 (2)	0.0784 (17)	−0.0195 (17)	−0.0051 (14)	0.0110 (16)
C22	0.0680 (16)	0.0705 (16)	0.0959 (19)	−0.0032 (13)	0.0151 (14)	0.0108 (14)
N1	0.0442 (9)	0.0510 (9)	0.0446 (8)	−0.0017 (7)	0.0026 (7)	0.0025 (7)
N2	0.0441 (9)	0.0563 (10)	0.0567 (9)	−0.0018 (8)	0.0021 (7)	0.0118 (8)
O1	0.0509 (8)	0.0552 (8)	0.0664 (8)	−0.0035 (7)	0.0000 (6)	0.0211 (7)
S1	0.0432 (3)	0.0684 (4)	0.0752 (4)	0.0020 (3)	0.0088 (2)	0.0171 (3)
S2	0.0586 (4)	0.0827 (4)	0.0809 (4)	−0.0146 (3)	0.0027 (3)	0.0257 (3)

C1—N1	1.301 (2)	C12—H12	0.9300
C1—C2	1.474 (2)	C13—C14	1.467 (2)
C1—C14	1.480 (2)	C14—O1	1.235 (2)
C2—C3	1.398 (2)	C15—N2	1.358 (2)
C2—C7	1.402 (2)	C15—S2	1.6432 (19)
C3—C4	1.370 (3)	C15—S1	1.739 (2)
C3—H3	0.9300	C16—C17	1.505 (3)
C4—C5	1.380 (3)	C16—S1	1.808 (2)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.371 (3)	C16—H16B	0.9700
C5—H5	0.9300	C17—C18	1.374 (3)
C6—C7	1.399 (2)	C17—C22	1.378 (3)
C6—H6	0.9300	C18—C19	1.382 (3)
C7—C8	1.478 (2)	C18—H18	0.9300
C8—C9	1.390 (3)	C19—C20	1.359 (4)
C8—C13	1.401 (2)	C19—H19	0.9300
C9—C10	1.380 (3)	C20—C21	1.367 (4)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.378 (3)	C21—C22	1.380 (3)
C10—H10	0.9300	C21—H21	0.9300
C11—C12	1.371 (3)	C22—H22	0.9300
C11—H11	0.9300	N1—N2	1.341 (2)
C12—C13	1.390 (2)	N2—H2	0.8600

N1—C1—C2	116.18 (15)	C12—C13—C14	118.28 (16)
N1—C1—C14	124.21 (16)	C8—C13—C14	120.78 (15)
C2—C1—C14	119.60 (15)	O1—C14—C13	121.05 (16)
C3—C2—C7	119.49 (16)	O1—C14—C1	120.66 (16)
C3—C2—C1	120.34 (16)	C13—C14—C1	118.29 (15)
C7—C2—C1	120.17 (15)	N2—C15—S2	119.68 (15)
C4—C3—C2	121.05 (18)	N2—C15—S1	112.82 (14)
C4—C3—H3	119.5	S2—C15—S1	127.49 (12)
C2—C3—H3	119.5	C17—C16—S1	108.87 (15)
C3—C4—C5	119.87 (18)	C17—C16—H16A	109.9
C3—C4—H4	120.1	S1—C16—H16A	109.9
C5—C4—H4	120.1	C17—C16—H16B	109.9
C6—C5—C4	119.87 (18)	S1—C16—H16B	109.9
C6—C5—H5	120.1	H16A—C16—H16B	108.3
C4—C5—H5	120.1	C18—C17—C22	119.0 (2)
C5—C6—C7	121.82 (18)	C18—C17—C16	120.7 (2)
C5—C6—H6	119.1	C22—C17—C16	120.3 (2)
C7—C6—H6	119.1	C17—C18—C19	120.2 (2)
C6—C7—C2	117.90 (16)	C17—C18—H18	119.9
C6—C7—C8	121.88 (16)	C19—C18—H18	119.9
C2—C7—C8	120.22 (15)	C20—C19—C18	120.3 (3)
C9—C8—C13	117.11 (17)	C20—C19—H19	119.9
C9—C8—C7	121.96 (17)	C18—C19—H19	119.9
C13—C8—C7	120.92 (15)	C19—C20—C21	120.3 (3)
C10—C9—C8	121.44 (19)	C19—C20—H20	119.8
C10—C9—H9	119.3	C21—C20—H20	119.8
C8—C9—H9	119.3	C20—C21—C22	119.7 (3)
C11—C10—C9	120.78 (19)	C20—C21—H21	120.2
C11—C10—H10	119.6	C22—C21—H21	120.2
C9—C10—H10	119.6	C17—C22—C21	120.5 (3)
C12—C11—C10	119.03 (19)	C17—C22—H22	119.7
C12—C11—H11	120.5	C21—C22—H22	119.7
C10—C11—H11	120.5	C1—N1—N2	119.66 (15)
C11—C12—C13	120.71 (18)	N1—N2—C15	120.22 (16)
C11—C12—H12	119.6	N1—N2—H2	119.9
C13—C12—H12	119.6	C15—N2—H2	119.9
C12—C13—C8	120.93 (16)	C15—S1—C16	100.92 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.89	2.560 (2)	134
C12—H12···O1ⁱ	0.93	2.42	3.239 (2)	147
C5—H5···Cg1ⁱⁱ	0.93	2.76	3.559 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.89	2.560 (2)	134
C12—H12⋯O1ⁱ	0.93	2.42	3.239 (2)	147
C5—H5⋯Cg1ⁱⁱ	0.93	2.76	3.559 (2)	144

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C2–C7 ring.

3 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Benzyl 3-[(E,E)-3-phenyl-prop-2-enyl-idene]dithio-carbazate.

Authors: M T H Tarafder; K A Crouse; M Toihidul Islam; Suchada Chantrapromma; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-05-10

3. Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives.

Authors: Shashikant V Bhandari; Kailash G Bothara; Mayuresh K Raut; Ajit A Patil; Aniket P Sarkate; Vinod J Mokale
Journal: Bioorg Med Chem Date: 2007-11-19 Impact factor: 3.641

3 in total