3,3′-Bis(3,4,5-trimethoxy­benzo­yl)-1,1′-(o-phenyl­ene)dithio­urea ethanol solvate

Du, H.-T.; Du, H.-J.

doi:10.1107/S1600536808023556

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1632-o1633

doi:10.1107/S1600536808023556

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3,3′-Bis(3,4,5-trimethoxybenzoyl)-1,1′-(o-phenylene)dithiourea ethanol solvate

Hai-Tang Du ^a ^* and Hai-Jun Du ^b

^aInstitute of Natural Products, Research Center for Eco-Environmental Sciences, Guiyang College, Guiyang 550005, People's Republic of China, and ^bSchool of Chemistry and Environmental Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: haitangdu@gz139.com.cn

(Received 24 July 2008; accepted 25 July 2008; online 31 July 2008)

In the molecule of the title compound, C₂₈H₃₀N₄O₈S₂·C₂H₆O, the benzene ring is oriented at dihedral angles of 38.50 (6) and 5.68 (5)° with respect to the trimethoxyphenyl rings, while the two trimethoxyphenyl rings are oriented at a dihedral angle of 44.18 (5)°. Intramolecular N—H⋯O and N—H⋯S hydrogen bonds result in the formation of non-planar six-, seven- and eight-membered rings. The twisting modes of the two side arms are different [C—N—C—O and C—N—C—N torsion angles = 0.1 (3) and 11.8 (3)°, respectively, in one arm, and 4.6 (3) and −11.5 (3)° in the other]. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules.

Related literature

For a related structure, see: Thiam et al. (2008 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₈H₃₀N₄O₈S₂·C₂H₆O
M_r = 660.75
Triclinic, $[P \overline 1]$
a = 7.7619 (15) Å
b = 14.473 (3) Å
c = 15.810 (3) Å
α = 67.113 (10)°
β = 73.069 (9)°
γ = 78.210 (12)°
V = 1556.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 113 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.968, T_max = 0.977
18692 measured reflections
6824 independent reflections
5694 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.115
S = 1.07
6824 reflections
433 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.90 (2)	2.51 (2)	3.403 (2)	173 (2)
N2—H2⋯S1	0.88 (2)	2.69 (2)	3.3527 (19)	133.0 (18)
N2—H2⋯O2	0.88 (2)	1.97 (2)	2.677 (2)	136 (2)
N1—H1⋯O1	0.89 (2)	1.90 (2)	2.621 (2)	137 (2)
N3—H3A⋯O9	0.84 (2)	2.23 (2)	2.949 (2)	145 (2)
O9—H9⋯O2	0.80 (3)	2.13 (3)	2.905 (2)	163 (3)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023556/hk2504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023556/hk2504Isup2.hkl

checkCIF report

Comment top

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C1-C6), B (C9-C14) and C (C17-C22) are, of course, planar, and the dihedral angles between them are A/B = 38.50 (6)°, A/C = 5.68 (5)° and B/C = 44.18 (5)°.

The intramolecular N-H···O and N-H···S hydrogen bonds (Table 1) result in the formation of non-planar six-, seven- and eight-membered rings: D (O1/N1/N3/C7/C8/H1), E (O2/N2/N4/C15/C16/H2), F (S1/N1/N2/C1/C2/C7/H2) and G (S1/O2/O9/N3/C7/H2/H3A/H9). Rings D and E adopt flattened-boat [ϕ = 171.38 (2)°, θ = 109.10 (3)° (for ring D) and ϕ = -20.28 (3)°, θ = 96.87 (3)° (for ring E)] conformations, while rings F and G adopt highly twisted conformations having total puckering amplitudes, Q_T, of 0.160 (3), 0.109 (3), 2.486 (4) and 2.064 (4) Å, respectively (Cremer & Pople, 1975). The two side arms are not twisted in the same way, as evidenced by the torsion angles: C7-N3-C8-O1 [0.1 (3)°], C8-N3-C7-N1 [11.8 (3)°] and C15-N4-C16-O2 [4.6 (3)°], C16-N4-C15-N2 [-11.5 (3)°], as in 1,2-bis(N'-benzoylthioureido)- benzene (Thiam et al., 2008).

In the crystal structure, intermolecular N-H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Thiam et al. (2008). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, ammonium thiocyanate (30 mmol), 3,4,5-trimethoxylbenzoyl chloride (20 mmol), PEG-400 (0.2 mmol) and acetone (50 mL) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at room temperature for 1 h, then benzene-1,2-diamine (9.5 mmol) was added, and the mixture was stirred for 2 h. The mixture was poured into water (20 ml). The resulting solid was filtered, washed with water, and then dried. Crystals suitable for X-ray analysis were obtained by the recrystallization of the solid residue from a mixture of N,N-dimethyl- formamide/ethanol (1:1) by slow evaporation at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

3,3'-Bis(3,4,5-trimethoxybenzoyl)-1,1'-(o-phenylene)dithiourea ethanol solvate top

Crystal data top

C₂₈H₃₀N₄O₈S₂·C₂H₆O	Z = 2
M_r = 660.75	F(000) = 696
Triclinic, P1	D_x = 1.409 Mg m⁻³
Hall symbol: -P 1	Melting point: 475 K
a = 7.7619 (15) Å	Mo Kα radiation, λ = 0.71070 Å
b = 14.473 (3) Å	Cell parameters from 4542 reflections
c = 15.810 (3) Å	θ = 2.4–27.2°
α = 67.113 (10)°	µ = 0.23 mm⁻¹
β = 73.069 (9)°	T = 113 K
γ = 78.210 (12)°	Block, colorless
V = 1556.9 (5) Å³	0.14 × 0.12 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	6824 independent reflections
Radiation source: rotating anode	5694 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.046
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.2°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
T_min = 0.968, T_max = 0.977	l = −20→20
18692 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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0441P)² + 0.4672P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
6824 reflections	Δρ_max = 0.26 e Å⁻³
433 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0140 (12)

Crystal data top

C₂₈H₃₀N₄O₈S₂·C₂H₆O	γ = 78.210 (12)°
M_r = 660.75	V = 1556.9 (5) Å³
Triclinic, P1	Z = 2
a = 7.7619 (15) Å	Mo Kα radiation
b = 14.473 (3) Å	µ = 0.23 mm⁻¹
c = 15.810 (3) Å	T = 113 K
α = 67.113 (10)°	0.14 × 0.12 × 0.10 mm
β = 73.069 (9)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	6824 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	5694 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.977	R_int = 0.046
18692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.26 e Å⁻³
6824 reflections	Δρ_min = −0.32 e Å⁻³
433 parameters

Special details top

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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.47072 (7)	0.74462 (4)	0.51329 (3)	0.02065 (14)
S2	0.93034 (8)	0.44117 (4)	0.34131 (4)	0.02578 (15)
O1	1.02467 (19)	0.81993 (11)	0.48592 (9)	0.0250 (3)
O2	0.6648 (2)	0.51201 (10)	0.60921 (10)	0.0274 (4)
O3	1.2473 (2)	0.92569 (11)	0.70183 (10)	0.0286 (4)
O4	1.0727 (2)	0.82041 (11)	0.87598 (10)	0.0278 (4)
O5	0.7886 (2)	0.72356 (11)	0.90656 (10)	0.0287 (4)
O6	0.7859 (2)	0.27652 (10)	0.93150 (10)	0.0243 (3)
O7	0.7307 (2)	0.09337 (10)	0.94217 (9)	0.0244 (3)
O8	0.6871 (2)	0.06352 (10)	0.79539 (9)	0.0229 (3)
O9	0.5525 (2)	0.62076 (12)	0.74010 (11)	0.0285 (4)
H9	0.568 (4)	0.582 (2)	0.7125 (19)	0.043*
N1	0.8159 (2)	0.76073 (12)	0.41701 (11)	0.0177 (4)
H1	0.923 (3)	0.7772 (17)	0.4133 (16)	0.030 (7)*
N2	0.7346 (2)	0.57673 (12)	0.42050 (12)	0.0200 (4)
H2	0.685 (3)	0.5885 (17)	0.4737 (17)	0.028 (6)*
N3	0.7451 (2)	0.76939 (12)	0.56722 (12)	0.0184 (4)
H3A	0.673 (3)	0.7516 (17)	0.6201 (17)	0.026 (6)*
N4	0.7865 (2)	0.41196 (12)	0.52015 (11)	0.0198 (4)
H4A	0.830 (3)	0.3486 (19)	0.5237 (17)	0.036 (7)*
C1	0.7839 (3)	0.75352 (14)	0.33508 (13)	0.0175 (4)
C2	0.7479 (3)	0.66254 (14)	0.33554 (13)	0.0176 (4)
C3	0.7222 (3)	0.65850 (15)	0.25351 (14)	0.0207 (4)
H3	0.6911	0.5981	0.2539	0.025*
C4	0.7419 (3)	0.74278 (16)	0.17098 (14)	0.0238 (5)
H4	0.7272	0.7392	0.1148	0.029*
C5	0.7829 (3)	0.83206 (16)	0.17021 (14)	0.0249 (5)
H5	0.7987	0.8890	0.1134	0.030*
C6	0.8006 (3)	0.83775 (15)	0.25285 (14)	0.0213 (4)
H6	0.8242	0.8995	0.2532	0.026*
C7	0.6875 (3)	0.75825 (13)	0.49576 (13)	0.0167 (4)
C8	0.9074 (3)	0.79901 (14)	0.56059 (14)	0.0193 (4)
C9	0.9324 (3)	0.80961 (14)	0.64638 (14)	0.0191 (4)
C10	1.0706 (3)	0.86638 (14)	0.63139 (14)	0.0199 (4)
H10	1.1358	0.9001	0.5690	0.024*
C11	1.1123 (3)	0.87340 (15)	0.70806 (14)	0.0207 (4)
C12	1.0173 (3)	0.82339 (15)	0.80012 (14)	0.0217 (4)
C13	0.8750 (3)	0.76923 (15)	0.81379 (13)	0.0215 (4)
C14	0.8326 (3)	0.76151 (15)	0.73745 (14)	0.0219 (4)
H14	0.7370	0.7240	0.7471	0.026*
C15	0.8105 (3)	0.48263 (14)	0.42749 (14)	0.0189 (4)
C16	0.7225 (3)	0.42760 (15)	0.60517 (14)	0.0197 (4)
C17	0.7314 (3)	0.33652 (14)	0.69148 (13)	0.0180 (4)
C18	0.7536 (3)	0.35253 (15)	0.76900 (14)	0.0200 (4)
H18	0.7662	0.4182	0.7647	0.024*
C19	0.7570 (3)	0.27097 (15)	0.85280 (13)	0.0193 (4)
C20	0.7301 (3)	0.17510 (14)	0.86015 (13)	0.0187 (4)
C21	0.7114 (3)	0.16009 (14)	0.78097 (14)	0.0187 (4)
C22	0.7134 (3)	0.24057 (14)	0.69593 (13)	0.0172 (4)
H22	0.7026	0.2304	0.6419	0.021*
C23	1.3530 (3)	0.97237 (17)	0.60921 (16)	0.0301 (5)
H23A	1.4118	0.9209	0.5812	0.045*
H23B	1.4455	1.0069	0.6127	0.045*
H23C	1.2744	1.0214	0.5701	0.045*
C24	0.9843 (3)	0.89960 (16)	0.91201 (15)	0.0274 (5)
H24A	1.0110	0.9651	0.8628	0.041*
H24B	1.0285	0.8918	0.9667	0.041*
H24C	0.8532	0.8958	0.9311	0.041*
C25	0.6375 (3)	0.67215 (18)	0.92291 (16)	0.0349 (6)
H25A	0.5474	0.7192	0.8903	0.052*
H25B	0.5834	0.6455	0.9909	0.052*
H25C	0.6777	0.6164	0.8988	0.052*
C26	0.8306 (3)	0.37088 (16)	0.92470 (15)	0.0277 (5)
H26A	0.9337	0.3926	0.8709	0.042*
H26B	0.8624	0.3629	0.9829	0.042*
H26C	0.7262	0.4217	0.9156	0.042*
C27	0.5853 (3)	0.09950 (17)	1.02149 (16)	0.0348 (6)
H27A	0.6219	0.1337	1.0552	0.052*
H27B	0.5573	0.0314	1.0643	0.052*
H27C	0.4777	0.1376	0.9989	0.052*
C28	0.6740 (3)	0.04397 (15)	0.71577 (14)	0.0249 (5)
H28A	0.5684	0.0849	0.6929	0.037*
H28B	0.6608	−0.0276	0.7343	0.037*
H28C	0.7839	0.0613	0.6654	0.037*
C29	0.3609 (3)	0.63770 (18)	0.77554 (16)	0.0312 (5)
H29A	0.2987	0.6509	0.7249	0.037*
H29B	0.3343	0.6983	0.7937	0.037*
C30	0.2880 (4)	0.5489 (2)	0.85986 (17)	0.0428 (7)
H30A	0.3103	0.4893	0.8416	0.064*
H30B	0.1575	0.5639	0.8824	0.064*
H30C	0.3489	0.5358	0.9103	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0181 (3)	0.0241 (3)	0.0211 (3)	−0.00133 (19)	−0.0054 (2)	−0.0093 (2)
S2	0.0320 (3)	0.0201 (3)	0.0198 (3)	0.0011 (2)	−0.0011 (2)	−0.0068 (2)
O1	0.0240 (8)	0.0343 (8)	0.0179 (7)	−0.0081 (6)	−0.0015 (6)	−0.0103 (6)
O2	0.0436 (10)	0.0171 (7)	0.0200 (8)	0.0031 (6)	−0.0090 (7)	−0.0070 (6)
O3	0.0308 (9)	0.0363 (9)	0.0256 (8)	−0.0101 (7)	−0.0086 (7)	−0.0137 (7)
O4	0.0350 (9)	0.0317 (8)	0.0237 (8)	0.0064 (6)	−0.0154 (7)	−0.0160 (7)
O5	0.0367 (9)	0.0332 (8)	0.0156 (7)	−0.0084 (7)	−0.0045 (6)	−0.0069 (6)
O6	0.0353 (9)	0.0211 (7)	0.0203 (7)	−0.0044 (6)	−0.0106 (6)	−0.0076 (6)
O7	0.0329 (9)	0.0187 (7)	0.0160 (7)	0.0021 (6)	−0.0059 (6)	−0.0024 (6)
O8	0.0356 (9)	0.0149 (7)	0.0202 (7)	−0.0050 (6)	−0.0100 (6)	−0.0046 (6)
O9	0.0278 (9)	0.0318 (9)	0.0286 (9)	−0.0028 (7)	−0.0046 (7)	−0.0149 (7)
N1	0.0187 (9)	0.0202 (8)	0.0159 (8)	−0.0019 (6)	−0.0051 (7)	−0.0073 (7)
N2	0.0280 (10)	0.0165 (8)	0.0142 (8)	−0.0005 (7)	−0.0056 (7)	−0.0045 (7)
N3	0.0199 (9)	0.0227 (9)	0.0134 (8)	−0.0030 (7)	−0.0032 (7)	−0.0074 (7)
N4	0.0268 (10)	0.0137 (8)	0.0165 (8)	−0.0013 (7)	−0.0036 (7)	−0.0041 (7)
C1	0.0152 (10)	0.0219 (10)	0.0155 (9)	0.0005 (7)	−0.0032 (7)	−0.0084 (8)
C2	0.0171 (10)	0.0183 (9)	0.0158 (9)	0.0013 (7)	−0.0035 (8)	−0.0061 (8)
C3	0.0218 (11)	0.0214 (10)	0.0202 (10)	0.0017 (8)	−0.0066 (8)	−0.0094 (8)
C4	0.0252 (11)	0.0293 (11)	0.0184 (10)	0.0045 (8)	−0.0084 (8)	−0.0112 (9)
C5	0.0285 (12)	0.0248 (11)	0.0155 (10)	0.0012 (8)	−0.0048 (9)	−0.0031 (8)
C6	0.0229 (11)	0.0174 (10)	0.0197 (10)	−0.0010 (8)	−0.0031 (8)	−0.0043 (8)
C7	0.0219 (10)	0.0131 (9)	0.0151 (9)	0.0000 (7)	−0.0069 (8)	−0.0039 (7)
C8	0.0206 (10)	0.0176 (9)	0.0205 (10)	−0.0003 (7)	−0.0067 (8)	−0.0071 (8)
C9	0.0209 (10)	0.0194 (10)	0.0195 (10)	0.0019 (8)	−0.0069 (8)	−0.0098 (8)
C10	0.0201 (10)	0.0198 (10)	0.0190 (10)	0.0009 (8)	−0.0057 (8)	−0.0066 (8)
C11	0.0210 (11)	0.0215 (10)	0.0234 (10)	0.0007 (8)	−0.0072 (8)	−0.0117 (8)
C12	0.0263 (11)	0.0229 (10)	0.0208 (10)	0.0051 (8)	−0.0121 (9)	−0.0119 (8)
C13	0.0254 (11)	0.0217 (10)	0.0151 (10)	0.0019 (8)	−0.0055 (8)	−0.0056 (8)
C14	0.0241 (11)	0.0213 (10)	0.0212 (10)	−0.0013 (8)	−0.0063 (8)	−0.0083 (8)
C15	0.0197 (10)	0.0178 (9)	0.0201 (10)	−0.0032 (7)	−0.0058 (8)	−0.0061 (8)
C16	0.0222 (10)	0.0197 (10)	0.0180 (10)	−0.0037 (8)	−0.0055 (8)	−0.0063 (8)
C17	0.0176 (10)	0.0189 (10)	0.0158 (9)	0.0005 (7)	−0.0034 (8)	−0.0057 (8)
C18	0.0217 (10)	0.0182 (10)	0.0211 (10)	−0.0023 (7)	−0.0051 (8)	−0.0077 (8)
C19	0.0195 (10)	0.0240 (10)	0.0150 (9)	−0.0009 (8)	−0.0047 (8)	−0.0077 (8)
C20	0.0199 (10)	0.0173 (9)	0.0159 (9)	−0.0013 (7)	−0.0047 (8)	−0.0027 (8)
C21	0.0176 (10)	0.0161 (9)	0.0233 (10)	−0.0024 (7)	−0.0054 (8)	−0.0071 (8)
C22	0.0175 (10)	0.0187 (9)	0.0149 (9)	−0.0020 (7)	−0.0037 (7)	−0.0051 (8)
C23	0.0306 (13)	0.0312 (12)	0.0327 (12)	−0.0105 (9)	−0.0052 (10)	−0.0137 (10)
C24	0.0357 (13)	0.0284 (11)	0.0226 (11)	−0.0013 (9)	−0.0092 (9)	−0.0129 (9)
C25	0.0463 (15)	0.0343 (13)	0.0222 (11)	−0.0170 (11)	0.0012 (10)	−0.0083 (10)
C26	0.0365 (13)	0.0264 (11)	0.0263 (11)	−0.0053 (9)	−0.0096 (10)	−0.0129 (9)
C27	0.0348 (13)	0.0300 (12)	0.0250 (12)	−0.0045 (10)	0.0006 (10)	0.0008 (10)
C28	0.0355 (13)	0.0191 (10)	0.0235 (11)	−0.0022 (8)	−0.0110 (9)	−0.0086 (9)
C29	0.0277 (12)	0.0373 (13)	0.0277 (12)	−0.0028 (9)	−0.0076 (10)	−0.0100 (10)
C30	0.0557 (17)	0.0482 (16)	0.0263 (13)	−0.0224 (13)	0.0021 (12)	−0.0150 (12)

Geometric parameters (Å, º) top

S1—C7	1.664 (2)	C9—C10	1.393 (3)
S2—C15	1.659 (2)	C9—C14	1.396 (3)
O1—C8	1.234 (2)	C10—C11	1.386 (3)
O2—C16	1.232 (2)	C10—H10	0.9500
O3—C11	1.373 (2)	C11—C12	1.400 (3)
O3—C23	1.425 (3)	C12—C13	1.402 (3)
O4—C12	1.370 (2)	C13—C14	1.389 (3)
O4—C24	1.438 (2)	C14—H14	0.9500
O5—C13	1.375 (2)	C16—C17	1.491 (3)
O5—C25	1.423 (3)	C17—C18	1.395 (3)
O6—C19	1.361 (2)	C17—C22	1.397 (3)
O6—C26	1.433 (2)	C18—C19	1.393 (3)
O7—C20	1.374 (2)	C18—H18	0.9500
O7—C27	1.441 (3)	C19—C20	1.400 (3)
O8—C21	1.370 (2)	C20—C21	1.402 (3)
O8—C28	1.428 (2)	C21—C22	1.393 (3)
O9—C29	1.434 (3)	C22—H22	0.9500
O9—H9	0.80 (3)	C23—H23A	0.9800
N1—C7	1.342 (2)	C23—H23B	0.9800
N1—C1	1.433 (3)	C23—H23C	0.9800
N1—H1	0.89 (2)	C24—H24A	0.9800
N2—C15	1.344 (3)	C24—H24B	0.9800
N2—C2	1.425 (2)	C24—H24C	0.9800
N2—H2	0.88 (2)	C25—H25A	0.9800
N3—C8	1.375 (3)	C25—H25B	0.9800
N3—C7	1.403 (3)	C25—H25C	0.9800
N3—H3A	0.84 (2)	C26—H26A	0.9800
N4—C16	1.381 (3)	C26—H26B	0.9800
N4—C15	1.407 (2)	C26—H26C	0.9800
N4—H4A	0.90 (2)	C27—H27A	0.9800
C1—C6	1.388 (3)	C27—H27B	0.9800
C1—C2	1.398 (3)	C27—H27C	0.9800
C2—C3	1.393 (3)	C28—H28A	0.9800
C3—C4	1.391 (3)	C28—H28B	0.9800
C3—H3	0.9500	C28—H28C	0.9800
C4—C5	1.387 (3)	C29—C30	1.508 (3)
C4—H4	0.9500	C29—H29A	0.9900
C5—C6	1.388 (3)	C29—H29B	0.9900
C5—H5	0.9500	C30—H30A	0.9800
C6—H6	0.9500	C30—H30B	0.9800
C8—C9	1.493 (3)	C30—H30C	0.9800

C11—O3—C23	116.05 (16)	C18—C17—C22	121.48 (17)
C12—O4—C24	114.05 (15)	C18—C17—C16	116.36 (18)
C13—O5—C25	116.56 (17)	C22—C17—C16	122.13 (18)
C19—O6—C26	117.41 (16)	C19—C18—C17	119.18 (18)
C20—O7—C27	114.85 (15)	C19—C18—H18	120.4
C21—O8—C28	117.05 (15)	C17—C18—H18	120.4
C29—O9—H9	107.2 (19)	O6—C19—C18	124.44 (18)
C7—N1—C1	124.35 (17)	O6—C19—C20	115.37 (17)
C7—N1—H1	116.3 (15)	C18—C19—C20	120.19 (18)
C1—N1—H1	118.6 (15)	O7—C20—C19	121.59 (18)
C15—N2—C2	125.79 (17)	O7—C20—C21	118.60 (17)
C15—N2—H2	117.3 (15)	C19—C20—C21	119.73 (17)
C2—N2—H2	116.3 (15)	O8—C21—C22	124.37 (18)
C8—N3—C7	127.62 (17)	O8—C21—C20	115.14 (17)
C8—N3—H3A	118.5 (16)	C22—C21—C20	120.47 (18)
C7—N3—H3A	113.8 (16)	C21—C22—C17	118.83 (18)
C16—N4—C15	129.46 (17)	C21—C22—H22	120.6
C16—N4—H4A	116.0 (15)	C17—C22—H22	120.6
C15—N4—H4A	114.3 (15)	O3—C23—H23A	109.5
C6—C1—C2	120.34 (18)	O3—C23—H23B	109.5
C6—C1—N1	118.33 (18)	H23A—C23—H23B	109.5
C2—C1—N1	121.21 (17)	O3—C23—H23C	109.5
C3—C2—C1	119.20 (18)	H23A—C23—H23C	109.5
C3—C2—N2	121.58 (18)	H23B—C23—H23C	109.5
C1—C2—N2	119.21 (17)	O4—C24—H24A	109.5
C4—C3—C2	120.1 (2)	O4—C24—H24B	109.5
C4—C3—H3	120.0	H24A—C24—H24B	109.5
C2—C3—H3	120.0	O4—C24—H24C	109.5
C5—C4—C3	120.44 (19)	H24A—C24—H24C	109.5
C5—C4—H4	119.8	H24B—C24—H24C	109.5
C3—C4—H4	119.8	O5—C25—H25A	109.5
C4—C5—C6	119.65 (19)	O5—C25—H25B	109.5
C4—C5—H5	120.2	H25A—C25—H25B	109.5
C6—C5—H5	120.2	O5—C25—H25C	109.5
C5—C6—C1	120.21 (19)	H25A—C25—H25C	109.5
C5—C6—H6	119.9	H25B—C25—H25C	109.5
C1—C6—H6	119.9	O6—C26—H26A	109.5
N1—C7—N3	115.67 (17)	O6—C26—H26B	109.5
N1—C7—S1	125.33 (15)	H26A—C26—H26B	109.5
N3—C7—S1	118.99 (14)	O6—C26—H26C	109.5
O1—C8—N3	121.57 (18)	H26A—C26—H26C	109.5
O1—C8—C9	121.22 (18)	H26B—C26—H26C	109.5
N3—C8—C9	117.16 (17)	O7—C27—H27A	109.5
C10—C9—C14	120.91 (19)	O7—C27—H27B	109.5
C10—C9—C8	115.91 (17)	H27A—C27—H27B	109.5
C14—C9—C8	123.07 (18)	O7—C27—H27C	109.5
C11—C10—C9	119.59 (18)	H27A—C27—H27C	109.5
C11—C10—H10	120.2	H27B—C27—H27C	109.5
C9—C10—H10	120.2	O8—C28—H28A	109.5
O3—C11—C10	124.62 (18)	O8—C28—H28B	109.5
O3—C11—C12	114.95 (18)	H28A—C28—H28B	109.5
C10—C11—C12	120.41 (19)	O8—C28—H28C	109.5
O4—C12—C11	120.25 (19)	H28A—C28—H28C	109.5
O4—C12—C13	120.29 (18)	H28B—C28—H28C	109.5
C11—C12—C13	119.24 (18)	O9—C29—C30	112.1 (2)
O5—C13—C14	124.23 (19)	O9—C29—H29A	109.2
O5—C13—C12	115.03 (18)	C30—C29—H29A	109.2
C14—C13—C12	120.71 (18)	O9—C29—H29B	109.2
C13—C14—C9	119.08 (19)	C30—C29—H29B	109.2
C13—C14—H14	120.5	H29A—C29—H29B	107.9
C9—C14—H14	120.5	C29—C30—H30A	109.5
N2—C15—N4	114.99 (17)	C29—C30—H30B	109.5
N2—C15—S2	128.09 (15)	H30A—C30—H30B	109.5
N4—C15—S2	116.90 (14)	C29—C30—H30C	109.5
O2—C16—N4	121.94 (18)	H30A—C30—H30C	109.5
O2—C16—C17	122.15 (18)	H30B—C30—H30C	109.5
N4—C16—C17	115.90 (17)

C7—N1—C1—C6	112.1 (2)	C11—C12—C13—O5	−179.33 (17)
C7—N1—C1—C2	−71.9 (2)	O4—C12—C13—C14	−171.96 (17)
C6—C1—C2—C3	−2.4 (3)	C11—C12—C13—C14	2.6 (3)
N1—C1—C2—C3	−178.42 (17)	O5—C13—C14—C9	−178.68 (18)
C6—C1—C2—N2	178.93 (17)	C12—C13—C14—C9	−0.8 (3)
N1—C1—C2—N2	2.9 (3)	C10—C9—C14—C13	−1.2 (3)
C15—N2—C2—C3	46.2 (3)	C8—C9—C14—C13	174.92 (18)
C15—N2—C2—C1	−135.2 (2)	C2—N2—C15—N4	176.38 (18)
C1—C2—C3—C4	3.5 (3)	C2—N2—C15—S2	−2.4 (3)
N2—C2—C3—C4	−177.94 (18)	C16—N4—C15—N2	−11.5 (3)
C2—C3—C4—C5	−1.6 (3)	C16—N4—C15—S2	167.45 (17)
C3—C4—C5—C6	−1.3 (3)	C15—N4—C16—O2	4.6 (3)
C4—C5—C6—C1	2.3 (3)	C15—N4—C16—C17	−174.03 (19)
C2—C1—C6—C5	−0.5 (3)	O2—C16—C17—C18	−28.7 (3)
N1—C1—C6—C5	175.64 (18)	N4—C16—C17—C18	149.99 (18)
C1—N1—C7—N3	−178.21 (16)	O2—C16—C17—C22	149.5 (2)
C1—N1—C7—S1	1.0 (3)	N4—C16—C17—C22	−31.8 (3)
C8—N3—C7—N1	11.8 (3)	C22—C17—C18—C19	−0.3 (3)
C8—N3—C7—S1	−167.47 (15)	C16—C17—C18—C19	177.93 (18)
C7—N3—C8—O1	0.1 (3)	C26—O6—C19—C18	−5.4 (3)
C7—N3—C8—C9	177.21 (17)	C26—O6—C19—C20	174.43 (17)
O1—C8—C9—C10	15.1 (3)	C17—C18—C19—O6	176.90 (17)
N3—C8—C9—C10	−162.03 (17)	C17—C18—C19—C20	−2.9 (3)
O1—C8—C9—C14	−161.21 (19)	C27—O7—C20—C19	65.1 (3)
N3—C8—C9—C14	21.6 (3)	C27—O7—C20—C21	−118.3 (2)
C14—C9—C10—C11	1.4 (3)	O6—C19—C20—O7	0.9 (3)
C8—C9—C10—C11	−174.97 (17)	C18—C19—C20—O7	−179.27 (17)
C23—O3—C11—C10	−2.1 (3)	O6—C19—C20—C21	−175.70 (17)
C23—O3—C11—C12	176.46 (17)	C18—C19—C20—C21	4.1 (3)
C9—C10—C11—O3	178.88 (18)	C28—O8—C21—C22	4.0 (3)
C9—C10—C11—C12	0.4 (3)	C28—O8—C21—C20	−177.79 (17)
C24—O4—C12—C11	93.5 (2)	O7—C20—C21—O8	2.8 (3)
C24—O4—C12—C13	−92.0 (2)	C19—C20—C21—O8	179.51 (17)
O3—C11—C12—O4	−6.4 (3)	O7—C20—C21—C22	−178.87 (17)
C10—C11—C12—O4	172.17 (17)	C19—C20—C21—C22	−2.2 (3)
O3—C11—C12—C13	178.98 (17)	O8—C21—C22—C17	177.19 (17)
C10—C11—C12—C13	−2.4 (3)	C20—C21—C22—C17	−1.0 (3)
C25—O5—C13—C14	−5.1 (3)	C18—C17—C22—C21	2.2 (3)
C25—O5—C13—C12	176.94 (18)	C16—C17—C22—C21	−175.89 (18)
O4—C12—C13—O5	6.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.90 (2)	2.51 (2)	3.403 (2)	173 (2)
N2—H2···S1	0.88 (2)	2.69 (2)	3.3527 (19)	133.0 (18)
N2—H2···O2	0.88 (2)	1.97 (2)	2.677 (2)	136 (2)
N1—H1···O1	0.89 (2)	1.90 (2)	2.621 (2)	137 (2)
N3—H3A···O9	0.84 (2)	2.23 (2)	2.949 (2)	145 (2)
O9—H9···O2	0.80 (3)	2.13 (3)	2.905 (2)	163 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₀N₄O₈S₂·C₂H₆O
M_r	660.75
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.7619 (15), 14.473 (3), 15.810 (3)
α, β, γ (°)	67.113 (10), 73.069 (9), 78.210 (12)
V (Å³)	1556.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.968, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	18692, 6824, 5694
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.115, 1.07
No. of reflections	6824
No. of parameters	433
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.90 (2)	2.51 (2)	3.403 (2)	173 (2)
N2—H2···S1	0.88 (2)	2.69 (2)	3.3527 (19)	133.0 (18)
N2—H2···O2	0.88 (2)	1.97 (2)	2.677 (2)	136 (2)
N1—H1···O1	0.89 (2)	1.90 (2)	2.621 (2)	137 (2)
N3—H3A···O9	0.84 (2)	2.23 (2)	2.949 (2)	145 (2)
O9—H9···O2	0.80 (3)	2.13 (3)	2.905 (2)	163 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

The authors thank Guiyang College for financial support.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Rigaku/MSC. (2005). CrystalClear and CrystalStructure. 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
Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Pages o1632-o1633

doi:10.1107/S1600536808023556

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

3,3′-Bis(3,4,5-tri­meth­oxy­benzo­yl)-1,1′-(o-phenyl­ene)di­thio­urea ethanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-Bis(3,4,5-trimethoxybenzoyl)-1,1′-(o-phenylene)dithiourea ethanol solvate