(Z)-5-Benzene­carbothioyl-1,11-dimethyl-6-phenyl-5H-dibenzo[d,f][1,3]diazepine

Zhang, J.-X.; Ng, S.W.

doi:10.1107/S1600536811000092

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o364

doi:10.1107/S1600536811000092

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(Z)-5-Benzenecarbothioyl-1,11-dimethyl-6-phenyl-5H-dibenzo[d,f][1,3]diazepine

Jia-Xin Zhang ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 December 2010; accepted 4 January 2011; online 12 January 2011)

The seven-membered ring in the title compound, C₂₈H₂₂N₂S, has a two-coordinate N atom as well as a three-coordinate N atom. The ring adopts a boat-shaped conformation with two C atoms of one methylphenyl ring as the stern and the three-coordinate N atom as the prow. The N,N-dimethylethanethioamide fragment is nearly planar (r.m.s. deviation = 0.049 Å); the phenyl ring of the benzenecarbothioyl unit connected to the three-coordinate N atom is aligned at 83.72 (4)° with respect to the mean plane of this fragment. Weak intermolecular C—H⋯S hydrogen bonding is present in the crystal structure.

Related literature

For background to the synthesis of thioamides by the reaction of 1,1′-binaphthyl-2,2′-diamine with acyl chlorides and phosphorus pentasulfide, see: Shi et al. (2004 ).

Experimental

Crystal data

C₂₈H₂₂N₂S
M_r = 418.54
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7665 (18) Å
b = 11.605 (3) Å
c = 21.392 (5) Å
V = 2176.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 113 K
0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.958, T_max = 0.967
21933 measured reflections
5176 independent reflections
4527 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.085
S = 0.99
5176 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 2775 Friedel pairs
Flack parameter: −0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯S1ⁱ	0.95	2.86	3.7216 (18)	152
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000092/xu5136sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000092/xu5136Isup2.hkl

checkCIF report

Comment top

The two amino groups of 1,1'-binaphthyl-2,2'-diamine undergo condensation with acyl chlorides and phosphorus pentasulfide to yield bis(thioamides) (Shi et al., 2004). The present study represents a variation of this reaction by reacting a biphenyl dibenzamide derivative directly with phosphorus pentasulfide. The resulting compound (Scheme I) has only one carbonyl fragment replaced by a thiocarbonyl fragment as the other fragment has undergone cyclization (Scheme I). The compound features a seven-membered ring, with the two nitrogen atoms constituting members of a seven-membered ring.

Related literature top

For background to the synthesis of thioamides by the reaction of 1,1'-binaphthyl-2,2'-diamine with acyl chlorides and phosphorus pentasulfide, see: Shi et al. (2004).

Experimental top

N,N'-(6,6'-Dimethylbiphenyl-2,2'-diyl)dibenzamide (210 mg, 0.50 mmol) and phosphorus pentasulfide (111 mg, 0.5 mmol) in pyridine (2 ml) were heated at 393 K for 10 h. To the product was added 10% sodium hydroxide to a pH of about 10. The organic compound was extracted with ethyl acetate (3 x 20 ml). The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (eluent: ethyl acetate/petroleum ether 1/20) to give the title compound (46.8 mg, 20%) as a yellow solid. Single crystals were obtained upon recrystallized from a dichloromethane-hexane mixture.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₈H₂₂N₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(Z)-5-Benzenecarbothioyl-1,11-dimethyl-6-phenyl-5H- dibenzo[d,f][1,3]diazepine top

Crystal data top

C₂₈H₂₂N₂S	F(000) = 880
M_r = 418.54	D_x = 1.277 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7653 reflections
a = 8.7665 (18) Å	θ = 1.9–27.9°
b = 11.605 (3) Å	µ = 0.17 mm⁻¹
c = 21.392 (5) Å	T = 113 K
V = 2176.4 (8) Å³	Block, yellow
Z = 4	0.26 × 0.22 × 0.20 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5176 independent reflections
Radiation source: rotating anode	4527 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.050
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω and ϕ scans	h = −11→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
T_min = 0.958, T_max = 0.967	l = −28→28
21933 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0493P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
5176 reflections	Δρ_max = 0.19 e Å⁻³
282 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2775 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (6)

Crystal data top

C₂₈H₂₂N₂S	V = 2176.4 (8) Å³
M_r = 418.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7665 (18) Å	µ = 0.17 mm⁻¹
b = 11.605 (3) Å	T = 113 K
c = 21.392 (5) Å	0.26 × 0.22 × 0.20 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5176 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4527 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.967	R_int = 0.050
21933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.085	Δρ_max = 0.19 e Å⁻³
S = 0.99	Δρ_min = −0.23 e Å⁻³
5176 reflections	Absolute structure: Flack (1983), 2775 Friedel pairs
282 parameters	Absolute structure parameter: −0.03 (6)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.09723 (5)	0.47544 (4)	0.76793 (2)	0.02825 (11)
N1	0.95131 (14)	0.56476 (11)	0.67231 (6)	0.0178 (3)
N2	0.76743 (15)	0.41503 (11)	0.66647 (6)	0.0200 (3)
C1	0.88897 (18)	0.55478 (13)	0.56264 (7)	0.0187 (3)
C2	0.92563 (17)	0.62439 (13)	0.61387 (7)	0.0178 (3)
C3	0.91869 (17)	0.74326 (13)	0.61224 (7)	0.0209 (3)
H3	0.9482	0.7880	0.6474	0.025*
C4	0.86735 (18)	0.79547 (14)	0.55772 (8)	0.0240 (4)
H4	0.8658	0.8771	0.5546	0.029*
C5	0.81855 (18)	0.72897 (15)	0.50809 (8)	0.0237 (4)
H5	0.7770	0.7660	0.4723	0.028*
C6	0.82841 (18)	0.60889 (14)	0.50890 (7)	0.0214 (3)
C7	0.7658 (2)	0.54265 (15)	0.45397 (8)	0.0288 (4)
H7A	0.6619	0.5690	0.4449	0.043*
H7B	0.7641	0.4602	0.4640	0.043*
H7C	0.8307	0.5556	0.4173	0.043*
C8	0.91836 (18)	0.42900 (13)	0.56802 (7)	0.0194 (3)
C9	0.85781 (17)	0.36525 (13)	0.61850 (7)	0.0197 (3)
C10	0.88359 (19)	0.24726 (13)	0.62336 (8)	0.0248 (4)
H10	0.8367	0.2042	0.6559	0.030*
C11	0.9777 (2)	0.19306 (15)	0.58068 (8)	0.0293 (4)
H11	0.9968	0.1128	0.5843	0.035*
C12	1.0442 (2)	0.25546 (14)	0.53263 (8)	0.0270 (4)
H12	1.1099	0.2175	0.5039	0.032*
C13	1.01628 (18)	0.37322 (14)	0.52574 (7)	0.0221 (3)
C14	1.1039 (2)	0.43886 (15)	0.47629 (8)	0.0291 (4)
H14A	1.1978	0.3970	0.4660	0.044*
H14B	1.1298	0.5156	0.4921	0.044*
H14C	1.0409	0.4464	0.4387	0.044*
C15	1.08502 (18)	0.54891 (12)	0.70153 (7)	0.0193 (3)
C16	1.22481 (18)	0.59577 (13)	0.67023 (7)	0.0192 (3)
C17	1.29579 (18)	0.52874 (14)	0.62485 (7)	0.0228 (3)
H17	1.2494	0.4592	0.6111	0.027*
C18	1.43445 (19)	0.56342 (15)	0.59970 (8)	0.0271 (4)
H18	1.4845	0.5166	0.5696	0.032*
C19	1.49930 (19)	0.66606 (16)	0.61859 (8)	0.0272 (4)
H19	1.5942	0.6898	0.6015	0.033*
C20	1.4268 (2)	0.73423 (15)	0.66218 (8)	0.0284 (4)
H20A	1.4712	0.8055	0.6743	0.034*
C21	1.28956 (19)	0.69967 (14)	0.68849 (8)	0.0249 (4)
H21A	1.2403	0.7467	0.7187	0.030*
C22	0.81179 (17)	0.50720 (13)	0.69330 (7)	0.0196 (3)
C23	0.72239 (18)	0.56611 (13)	0.74184 (7)	0.0200 (3)
C24	0.58133 (17)	0.52104 (14)	0.75993 (7)	0.0226 (3)
H24	0.5459	0.4509	0.7423	0.027*
C25	0.4935 (2)	0.57849 (15)	0.80349 (8)	0.0269 (4)
H25	0.3987	0.5467	0.8164	0.032*
C26	0.5424 (2)	0.68208 (16)	0.82853 (8)	0.0312 (4)
H26	0.4804	0.7219	0.8579	0.037*
C27	0.6819 (2)	0.72744 (16)	0.81069 (9)	0.0348 (4)
H27	0.7159	0.7983	0.8280	0.042*
C28	0.7718 (2)	0.66969 (15)	0.76768 (8)	0.0279 (4)
H28	0.8677	0.7009	0.7557	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0262 (2)	0.0317 (2)	0.0269 (2)	−0.00369 (19)	−0.00223 (19)	0.01130 (18)
N1	0.0185 (7)	0.0179 (6)	0.0171 (6)	−0.0035 (5)	0.0025 (5)	0.0004 (5)
N2	0.0197 (7)	0.0204 (7)	0.0198 (6)	−0.0026 (5)	0.0019 (6)	0.0006 (5)
C1	0.0164 (8)	0.0212 (8)	0.0183 (7)	−0.0023 (6)	0.0034 (6)	0.0007 (6)
C2	0.0147 (8)	0.0211 (8)	0.0177 (7)	−0.0017 (6)	0.0023 (6)	0.0025 (6)
C3	0.0175 (8)	0.0197 (7)	0.0256 (8)	−0.0021 (6)	0.0024 (7)	−0.0020 (6)
C4	0.0205 (9)	0.0187 (8)	0.0328 (9)	0.0001 (6)	0.0026 (7)	0.0050 (7)
C5	0.0193 (9)	0.0281 (9)	0.0236 (8)	−0.0005 (7)	0.0018 (7)	0.0069 (7)
C6	0.0184 (8)	0.0241 (8)	0.0215 (8)	−0.0019 (6)	0.0028 (7)	0.0036 (7)
C7	0.0318 (9)	0.0323 (10)	0.0223 (8)	−0.0020 (8)	−0.0047 (8)	0.0015 (7)
C8	0.0181 (8)	0.0200 (7)	0.0202 (7)	−0.0006 (6)	−0.0016 (7)	−0.0020 (6)
C9	0.0163 (8)	0.0213 (8)	0.0214 (8)	−0.0020 (6)	−0.0018 (6)	−0.0025 (7)
C10	0.0255 (9)	0.0204 (8)	0.0285 (8)	−0.0034 (7)	−0.0046 (7)	0.0006 (7)
C11	0.0301 (9)	0.0186 (8)	0.0391 (10)	0.0029 (7)	−0.0038 (8)	−0.0032 (7)
C12	0.0239 (8)	0.0270 (9)	0.0300 (9)	0.0048 (7)	−0.0011 (7)	−0.0068 (7)
C13	0.0208 (8)	0.0240 (8)	0.0214 (8)	−0.0006 (7)	−0.0011 (7)	−0.0029 (7)
C14	0.0282 (9)	0.0339 (9)	0.0253 (8)	0.0005 (8)	0.0068 (8)	−0.0031 (7)
C15	0.0191 (8)	0.0158 (7)	0.0229 (8)	−0.0012 (6)	0.0002 (7)	−0.0030 (6)
C16	0.0161 (8)	0.0207 (7)	0.0208 (7)	0.0002 (6)	−0.0024 (7)	0.0054 (6)
C17	0.0238 (8)	0.0217 (8)	0.0230 (8)	0.0002 (7)	−0.0016 (7)	0.0035 (7)
C18	0.0269 (9)	0.0321 (9)	0.0223 (8)	0.0078 (7)	0.0042 (7)	0.0056 (7)
C19	0.0186 (8)	0.0374 (10)	0.0257 (9)	−0.0021 (7)	0.0009 (7)	0.0106 (8)
C20	0.0284 (10)	0.0289 (8)	0.0280 (9)	−0.0103 (7)	−0.0028 (8)	0.0061 (7)
C21	0.0252 (9)	0.0239 (8)	0.0256 (8)	−0.0021 (7)	0.0011 (7)	0.0000 (7)
C22	0.0176 (8)	0.0219 (8)	0.0193 (7)	−0.0036 (6)	0.0020 (6)	0.0032 (6)
C23	0.0190 (8)	0.0217 (7)	0.0192 (7)	0.0003 (6)	0.0019 (7)	0.0024 (6)
C24	0.0217 (8)	0.0244 (7)	0.0217 (7)	−0.0028 (7)	−0.0017 (7)	0.0025 (7)
C25	0.0189 (8)	0.0394 (10)	0.0226 (8)	−0.0012 (7)	0.0036 (7)	0.0034 (7)
C26	0.0304 (10)	0.0368 (9)	0.0265 (9)	0.0057 (8)	0.0071 (8)	−0.0022 (8)
C27	0.0392 (11)	0.0298 (10)	0.0353 (10)	−0.0039 (8)	0.0088 (9)	−0.0118 (8)
C28	0.0267 (9)	0.0279 (9)	0.0290 (9)	−0.0056 (7)	0.0070 (8)	−0.0052 (8)

Geometric parameters (Å, º) top

S1—C15	1.6601 (16)	C13—C14	1.513 (2)
N1—C15	1.341 (2)	C14—H14A	0.9800
N1—C2	1.4465 (19)	C14—H14B	0.9800
N1—C22	1.4642 (19)	C14—H14C	0.9800
N2—C22	1.275 (2)	C15—C16	1.499 (2)
N2—C9	1.419 (2)	C16—C21	1.389 (2)
C1—C2	1.399 (2)	C16—C17	1.391 (2)
C1—C6	1.413 (2)	C17—C18	1.389 (2)
C1—C8	1.487 (2)	C17—H17	0.9500
C2—C3	1.381 (2)	C18—C19	1.380 (2)
C3—C4	1.389 (2)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.378 (2)
C4—C5	1.381 (2)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.388 (2)
C5—C6	1.396 (2)	C20—H20A	0.9500
C5—H5	0.9500	C21—H21A	0.9500
C6—C7	1.508 (2)	C22—C23	1.470 (2)
C7—H7A	0.9800	C23—C24	1.397 (2)
C7—H7B	0.9800	C23—C28	1.392 (2)
C7—H7C	0.9800	C24—C25	1.380 (2)
C8—C13	1.405 (2)	C24—H24	0.9500
C8—C9	1.413 (2)	C25—C26	1.384 (3)
C9—C10	1.392 (2)	C25—H25	0.9500
C10—C11	1.382 (2)	C26—C27	1.385 (3)
C10—H10	0.9500	C26—H26	0.9500
C11—C12	1.386 (2)	C27—C28	1.385 (2)
C11—H11	0.9500	C27—H27	0.9500
C12—C13	1.396 (2)	C28—H28	0.9500
C12—H12	0.9500

C15—N1—C2	127.19 (12)	C13—C14—H14B	109.5
C15—N1—C22	121.64 (12)	H14A—C14—H14B	109.5
C2—N1—C22	110.69 (12)	C13—C14—H14C	109.5
C22—N2—C9	119.79 (13)	H14A—C14—H14C	109.5
C2—C1—C6	117.83 (14)	H14B—C14—H14C	109.5
C2—C1—C8	117.81 (13)	N1—C15—C16	117.18 (13)
C6—C1—C8	124.35 (14)	N1—C15—S1	121.71 (11)
C3—C2—C1	123.16 (14)	C16—C15—S1	121.06 (12)
C3—C2—N1	120.42 (14)	C21—C16—C17	119.94 (15)
C1—C2—N1	115.88 (13)	C21—C16—C15	121.58 (14)
C2—C3—C4	118.10 (15)	C17—C16—C15	118.34 (14)
C2—C3—H3	120.9	C18—C17—C16	119.99 (16)
C4—C3—H3	120.9	C18—C17—H17	120.0
C5—C4—C3	120.14 (15)	C16—C17—H17	120.0
C5—C4—H4	119.9	C19—C18—C17	119.80 (16)
C3—C4—H4	119.9	C19—C18—H18	120.1
C4—C5—C6	121.95 (16)	C17—C18—H18	120.1
C4—C5—H5	119.0	C18—C19—C20	120.25 (16)
C6—C5—H5	119.0	C18—C19—H19	119.9
C5—C6—C1	118.48 (15)	C20—C19—H19	119.9
C5—C6—C7	118.46 (15)	C19—C20—C21	120.55 (16)
C1—C6—C7	122.97 (14)	C19—C20—H20A	119.7
C6—C7—H7A	109.5	C21—C20—H20A	119.7
C6—C7—H7B	109.5	C16—C21—C20	119.43 (16)
H7A—C7—H7B	109.5	C16—C21—H21A	120.3
C6—C7—H7C	109.5	C20—C21—H21A	120.3
H7A—C7—H7C	109.5	N2—C22—N1	119.97 (14)
H7B—C7—H7C	109.5	N2—C22—C23	123.08 (14)
C13—C8—C9	118.71 (14)	N1—C22—C23	116.74 (13)
C13—C8—C1	120.56 (14)	C24—C23—C28	119.25 (15)
C9—C8—C1	120.55 (14)	C24—C23—C22	119.57 (14)
C10—C9—C8	120.75 (15)	C28—C23—C22	121.08 (14)
C10—C9—N2	115.93 (15)	C25—C24—C23	119.98 (15)
C8—C9—N2	123.32 (14)	C25—C24—H24	120.0
C11—C10—C9	119.71 (16)	C23—C24—H24	120.0
C11—C10—H10	120.1	C24—C25—C26	120.54 (16)
C9—C10—H10	120.1	C24—C25—H25	119.7
C10—C11—C12	120.21 (16)	C26—C25—H25	119.7
C10—C11—H11	119.9	C25—C26—C27	119.79 (17)
C12—C11—H11	119.9	C25—C26—H26	120.1
C11—C12—C13	121.07 (16)	C27—C26—H26	120.1
C11—C12—H12	119.5	C28—C27—C26	120.12 (17)
C13—C12—H12	119.5	C28—C27—H27	119.9
C12—C13—C8	119.35 (15)	C26—C27—H27	119.9
C12—C13—C14	118.53 (15)	C27—C28—C23	120.30 (16)
C8—C13—C14	121.89 (14)	C27—C28—H28	119.8
C13—C14—H14A	109.5	C23—C28—H28	119.8

C6—C1—C2—C3	−6.1 (2)	C9—C8—C13—C14	−170.84 (15)
C8—C1—C2—C3	173.00 (15)	C1—C8—C13—C14	4.3 (2)
C6—C1—C2—N1	165.46 (13)	C2—N1—C15—C16	−1.2 (2)
C8—C1—C2—N1	−15.4 (2)	C22—N1—C15—C16	170.10 (13)
C15—N1—C2—C3	−80.0 (2)	C2—N1—C15—S1	−178.48 (11)
C22—N1—C2—C3	107.88 (16)	C22—N1—C15—S1	−7.2 (2)
C15—N1—C2—C1	108.11 (17)	N1—C15—C16—C21	99.88 (18)
C22—N1—C2—C1	−63.97 (16)	S1—C15—C16—C21	−82.82 (18)
C1—C2—C3—C4	2.5 (2)	N1—C15—C16—C17	−84.55 (18)
N1—C2—C3—C4	−168.78 (13)	S1—C15—C16—C17	92.75 (16)
C2—C3—C4—C5	2.9 (2)	C21—C16—C17—C18	2.6 (2)
C3—C4—C5—C6	−4.4 (2)	C15—C16—C17—C18	−173.01 (14)
C4—C5—C6—C1	0.6 (2)	C16—C17—C18—C19	−1.8 (2)
C4—C5—C6—C7	177.21 (15)	C17—C18—C19—C20	−0.1 (3)
C2—C1—C6—C5	4.5 (2)	C18—C19—C20—C21	1.2 (3)
C8—C1—C6—C5	−174.62 (15)	C17—C16—C21—C20	−1.5 (2)
C2—C1—C6—C7	−171.95 (14)	C15—C16—C21—C20	173.97 (15)
C8—C1—C6—C7	9.0 (2)	C19—C20—C21—C16	−0.4 (3)
C2—C1—C8—C13	−121.05 (16)	C9—N2—C22—N1	3.3 (2)
C6—C1—C8—C13	58.0 (2)	C9—N2—C22—C23	177.90 (14)
C2—C1—C8—C9	54.0 (2)	C15—N1—C22—N2	−97.74 (18)
C6—C1—C8—C9	−126.86 (16)	C2—N1—C22—N2	74.85 (17)
C13—C8—C9—C10	−5.5 (2)	C15—N1—C22—C23	87.33 (17)
C1—C8—C9—C10	179.28 (15)	C2—N1—C22—C23	−100.07 (15)
C13—C8—C9—N2	175.05 (14)	N2—C22—C23—C24	−0.4 (2)
C1—C8—C9—N2	−0.1 (2)	N1—C22—C23—C24	174.33 (14)
C22—N2—C9—C10	132.30 (16)	N2—C22—C23—C28	−176.79 (16)
C22—N2—C9—C8	−48.3 (2)	N1—C22—C23—C28	−2.0 (2)
C8—C9—C10—C11	4.3 (2)	C28—C23—C24—C25	−0.7 (2)
N2—C9—C10—C11	−176.25 (15)	C22—C23—C24—C25	−177.15 (14)
C9—C10—C11—C12	−1.0 (3)	C23—C24—C25—C26	1.4 (2)
C10—C11—C12—C13	−0.9 (3)	C24—C25—C26—C27	−1.3 (3)
C11—C12—C13—C8	−0.4 (2)	C25—C26—C27—C28	0.4 (3)
C11—C12—C13—C14	174.18 (16)	C26—C27—C28—C23	0.4 (3)
C9—C8—C13—C12	3.6 (2)	C24—C23—C28—C27	−0.2 (2)
C1—C8—C13—C12	178.74 (15)	C22—C23—C28—C27	176.20 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S1ⁱ	0.95	2.86	3.7216 (18)	152

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂N₂S
M_r	418.54
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	8.7665 (18), 11.605 (3), 21.392 (5)
V (Å³)	2176.4 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.958, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	21933, 5176, 4527
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.085, 0.99
No. of reflections	5176
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23
Absolute structure	Flack (1983), 2775 Friedel pairs
Absolute structure parameter	−0.03 (6)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···S1ⁱ	0.95	2.86	3.7216 (18)	152

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Acknowledgements

We thank Beijing Normal University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, M., Duan, W.-L. & Rong, G.-B. (2004). Chirality, 16, 642–651. Web of Science CSD CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o364

doi:10.1107/S1600536811000092

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-5-Benzene­carbo­thioyl-1,11-di­methyl-6-phenyl-5H-dibenzo[d,f][1,3]diazepine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-5-Benzenecarbothioyl-1,11-dimethyl-6-phenyl-5H-dibenzo[d,f][1,3]diazepine