N-[2,4-Dioxo-3-aza­tricyclo­[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-3-yl]thio­urea

Al-Salahi, R.; Al-Omar, M.; Marzouk, M.; Ng, S.W.

doi:10.1107/S1600536812021812

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1811

doi:10.1107/S1600536812021812

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N-[2,4-Dioxo-3-azatricyclo[7.3.1.0^5,13]trideca-1(13),5,7,9,11-pentaen-3-yl]thiourea

Rashad Al-Salahi,^a Mohamed Al-Omar,^a Mohamed Marzouk ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 May 2012; accepted 14 May 2012; online 19 May 2012)

In the two independent molecules in the asymmetric unit of the title compound, C₁₃H₉N₃O₂S, the azatricyclotridecapentaene ring system is approximately planar with r.m.s. deviations of 0.022 and 0.033 Å. The urea unit connected to the fused rings is approximately perpendicular [dihedral angles = 82.4 (1) and 82.7 (1)°]. In the crystal, the molecules associate by N—H⋯O hydrogen bonds, forming a chain running along the a axis. The crystal studied was a non-merohedral twin with a fractional contribution of 49.6 (1)% for the minor domain.

Related literature

For background to the class of antitumor drugs, see; Pessoa et al. (2010 ).

Experimental

Crystal data

C₁₃H₉N₃O₂S
M_r = 271.29
Triclinic, $[P \overline 1]$
a = 4.5861 (2) Å
b = 11.0475 (4) Å
c = 22.5594 (9) Å
α = 89.196 (3)°
β = 88.073 (3)°
γ = 81.128 (3)°
V = 1128.61 (8) Å³
Z = 4
Cu Kα radiation
μ = 2.58 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.565, T_max = 0.927
14869 measured reflections
7974 independent reflections
7060 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.196
S = 1.11
7974 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.88	2.35	3.074 (3)	140
N2—H2⋯O1ⁱⁱ	0.88	2.33	2.993 (3)	132
N3—H31⋯O2ⁱⁱⁱ	0.88	2.09	2.912 (3)	154
N5—H5⋯O3ⁱⁱⁱ	0.88	2.55	3.301 (3)	144
N5—H5⋯O3^iv	0.88	2.52	2.988 (3)	114
N6—H61⋯O4ⁱ	0.88	2.21	3.015 (3)	152
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z+1; (iii) x+1, y, z; (iv) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812021812/bt5920sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021812/bt5920Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021812/bt5920Isup3.cml

checkCIF report

Comment top

1-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)thiourea is a powerful antitumor drug that is synthesized from phthalic anhydride and thiosemicarbazide (Pessoa et al., 2010). The title compound (Scheme I) is synthesized by using naphthalic acid anhydride in place of phthalic anhydride.

The crystal structure features two independent molecules. The azatricyclo-trideca-pentaene fused-ring is flat; the urea unit connected to the fused-ring is approximately perpendicular [dihedral angle 82.4 (1), 82.7 (1) °] (Fig. 1). Each independent molecule associates by an N–H···O hydrogen bond into a dimer; adjacent dimers are linked by N–H···O hydrogen bonds to form a chain running along the a-axis of the triclinic unit cell (Table 1).

Related literature top

For background to the class of antitumor drugs, see; Pessoa et al. (2010).

Experimental top

Naphthalic acid anhydride (2.2 mmol, 0.44 g) was dissolved in glacial acetic acid (15 ml). A solution of thiosemicarbazide (2.8 mmol, 0.26 g) in glacial acetic acid (10 ml) was added. A solid formed immediately. The solid was collected, washed with water and ether. The compound was recrystallized from a mixture of toluene and DMF to yield colorless crystals.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₃H₉N₃O₂S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N-(2,4-Dioxo-3-azatricyclo[7.3.1.0^5,13]trideca-1(13),5,7,9,11- pentaen-3-yl)thiourea top

Crystal data top

C₁₃H₉N₃O₂S	Z = 4
M_r = 271.29	F(000) = 560
Triclinic, P1	D_x = 1.597 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 4.5861 (2) Å	Cell parameters from 6016 reflections
b = 11.0475 (4) Å	θ = 3.9–76.4°
c = 22.5594 (9) Å	µ = 2.58 mm⁻¹
α = 89.196 (3)°	T = 100 K
β = 88.073 (3)°	Plate, colorless
γ = 81.128 (3)°	0.25 × 0.10 × 0.03 mm
V = 1128.61 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	7974 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	7060 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.076
Detector resolution: 10.4041 pixels mm^-1	θ_max = 77.5°, θ_min = 3.9°
ω scan	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
T_min = 0.565, T_max = 0.927	l = −28→24
14869 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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.196	w = 1/[σ²(F_o²) + (0.1312P)² + 0.6561P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
7974 reflections	Δρ_max = 0.47 e Å⁻³
345 parameters	Δρ_min = −0.73 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: 0.007 (1)

Crystal data top

C₁₃H₉N₃O₂S	γ = 81.128 (3)°
M_r = 271.29	V = 1128.61 (8) Å³
Triclinic, P1	Z = 4
a = 4.5861 (2) Å	Cu Kα radiation
b = 11.0475 (4) Å	µ = 2.58 mm⁻¹
c = 22.5594 (9) Å	T = 100 K
α = 89.196 (3)°	0.25 × 0.10 × 0.03 mm
β = 88.073 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	7974 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	7060 reflections with I > 2σ(I)
T_min = 0.565, T_max = 0.927	R_int = 0.076
14869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.196	H-atom parameters constrained
S = 1.11	Δρ_max = 0.47 e Å⁻³
7974 reflections	Δρ_min = −0.73 e Å⁻³
345 parameters

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

	x	y	z	U_iso*/U_eq
S1	−0.00401 (14)	0.90107 (6)	0.35711 (3)	0.02668 (18)
S2	1.03964 (15)	0.64485 (7)	−0.15038 (3)	0.03115 (19)
O1	0.3711 (4)	0.91572 (19)	0.53190 (8)	0.0280 (4)
O2	−0.2323 (4)	0.63074 (18)	0.50792 (8)	0.0247 (4)
O3	0.6884 (5)	0.5699 (2)	0.02003 (9)	0.0315 (4)
O4	1.2207 (4)	0.88347 (18)	0.01639 (9)	0.0268 (4)
N1	0.0726 (5)	0.7727 (2)	0.52057 (9)	0.0235 (4)
N2	−0.0298 (5)	0.8305 (2)	0.46861 (10)	0.0243 (5)
H2	−0.2080	0.8736	0.4689	0.029*
N3	0.3931 (5)	0.7492 (2)	0.41554 (10)	0.0255 (5)
H31	0.4532	0.7066	0.4473	0.031*
H32	0.5037	0.7429	0.3828	0.031*
N4	0.9302 (5)	0.7334 (2)	0.01767 (9)	0.0231 (4)
N5	1.0573 (5)	0.6935 (2)	−0.03728 (10)	0.0248 (5)
H5	1.2422	0.6574	−0.0398	0.030*
N6	0.6345 (5)	0.7835 (2)	−0.08405 (10)	0.0288 (5)
H61	0.5714	0.8196	−0.0505	0.035*
H62	0.5260	0.7957	−0.1156	0.035*
C1	0.1363 (6)	0.8228 (2)	0.41709 (11)	0.0231 (5)
C2	0.2727 (5)	0.8289 (3)	0.55335 (11)	0.0237 (5)
C3	0.3503 (5)	0.7740 (2)	0.61137 (11)	0.0228 (5)
C4	0.5301 (6)	0.8282 (3)	0.64730 (12)	0.0257 (5)
H4	0.6002	0.9012	0.6347	0.031*
C5	0.6094 (6)	0.7749 (3)	0.70274 (12)	0.0288 (6)
H5A	0.7324	0.8127	0.7274	0.035*
C6	0.5111 (6)	0.6693 (3)	0.72147 (12)	0.0277 (6)
H6	0.5666	0.6347	0.7590	0.033*
C7	0.3271 (5)	0.6110 (3)	0.68538 (11)	0.0241 (5)
C8	0.2256 (6)	0.5010 (3)	0.70251 (12)	0.0264 (5)
H8	0.2803	0.4639	0.7396	0.032*
C9	0.0490 (6)	0.4467 (3)	0.66639 (12)	0.0258 (5)
H9	−0.0141	0.3718	0.6783	0.031*
C10	−0.0390 (6)	0.5017 (3)	0.61165 (12)	0.0255 (5)
H10	−0.1647	0.4649	0.5872	0.031*
C11	0.0577 (5)	0.6086 (2)	0.59394 (11)	0.0222 (5)
C12	0.2453 (5)	0.6650 (2)	0.62956 (11)	0.0224 (5)
C13	−0.0487 (5)	0.6671 (2)	0.53792 (11)	0.0222 (5)
C14	0.8931 (6)	0.7108 (3)	−0.08703 (12)	0.0254 (5)
C15	0.7413 (6)	0.6591 (3)	0.04568 (12)	0.0254 (5)
C16	0.6217 (6)	0.6980 (3)	0.10479 (12)	0.0249 (5)
C17	0.4327 (6)	0.6302 (3)	0.13435 (13)	0.0294 (6)
H17	0.3849	0.5583	0.1169	0.035*
C18	0.3116 (6)	0.6675 (3)	0.19013 (13)	0.0330 (6)
H18	0.1787	0.6215	0.2100	0.040*
C19	0.3827 (6)	0.7698 (3)	0.21630 (13)	0.0325 (6)
H19	0.3023	0.7928	0.2546	0.039*
C20	0.5755 (6)	0.8421 (3)	0.18675 (12)	0.0286 (6)
C21	0.6513 (6)	0.9491 (3)	0.21190 (13)	0.0328 (6)
H21	0.5746	0.9737	0.2502	0.039*
C22	0.8338 (7)	1.0178 (3)	0.18183 (14)	0.0341 (6)
H22	0.8777	1.0907	0.1990	0.041*
C23	0.9566 (6)	0.9808 (3)	0.12557 (12)	0.0295 (6)
H23	1.0853	1.0281	0.1052	0.035*
C24	0.8896 (6)	0.8757 (3)	0.10003 (12)	0.0249 (5)
C25	0.6951 (6)	0.8056 (3)	0.12967 (12)	0.0258 (5)
C26	1.0303 (6)	0.8364 (3)	0.04201 (12)	0.0243 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0238 (3)	0.0370 (3)	0.0193 (3)	−0.0052 (2)	0.0006 (2)	0.0020 (2)
S2	0.0249 (3)	0.0490 (4)	0.0204 (3)	−0.0084 (3)	0.0019 (2)	−0.0066 (3)
O1	0.0271 (9)	0.0336 (10)	0.0251 (10)	−0.0113 (8)	0.0060 (7)	−0.0019 (8)
O2	0.0200 (9)	0.0343 (10)	0.0213 (9)	−0.0089 (7)	−0.0012 (7)	−0.0016 (7)
O3	0.0315 (10)	0.0392 (11)	0.0280 (10)	−0.0190 (8)	0.0005 (8)	−0.0043 (8)
O4	0.0201 (8)	0.0343 (10)	0.0275 (9)	−0.0092 (7)	0.0010 (7)	−0.0001 (8)
N1	0.0203 (10)	0.0334 (11)	0.0179 (10)	−0.0078 (9)	0.0001 (8)	0.0010 (9)
N2	0.0177 (10)	0.0338 (11)	0.0210 (10)	−0.0037 (8)	0.0010 (8)	0.0030 (9)
N3	0.0182 (10)	0.0368 (12)	0.0216 (11)	−0.0051 (9)	0.0017 (8)	−0.0020 (9)
N4	0.0168 (9)	0.0354 (11)	0.0184 (10)	−0.0090 (8)	0.0036 (8)	−0.0053 (9)
N5	0.0195 (10)	0.0359 (12)	0.0195 (10)	−0.0066 (8)	0.0028 (8)	−0.0043 (9)
N6	0.0195 (10)	0.0457 (13)	0.0212 (11)	−0.0053 (9)	0.0004 (8)	−0.0001 (10)
C1	0.0198 (11)	0.0286 (12)	0.0227 (12)	−0.0097 (9)	0.0007 (9)	−0.0034 (10)
C2	0.0172 (11)	0.0340 (13)	0.0209 (12)	−0.0079 (10)	0.0050 (9)	−0.0040 (10)
C3	0.0169 (11)	0.0310 (12)	0.0207 (12)	−0.0053 (9)	0.0029 (9)	−0.0031 (10)
C4	0.0193 (11)	0.0338 (13)	0.0254 (13)	−0.0083 (10)	0.0019 (10)	−0.0050 (10)
C5	0.0202 (12)	0.0404 (15)	0.0266 (13)	−0.0065 (11)	−0.0012 (10)	−0.0081 (11)
C6	0.0189 (12)	0.0444 (16)	0.0199 (12)	−0.0047 (11)	0.0004 (9)	−0.0052 (11)
C7	0.0184 (11)	0.0326 (13)	0.0212 (12)	−0.0044 (10)	0.0029 (9)	−0.0014 (10)
C8	0.0223 (12)	0.0344 (13)	0.0212 (12)	−0.0014 (10)	0.0038 (10)	0.0021 (10)
C9	0.0259 (12)	0.0283 (12)	0.0236 (12)	−0.0066 (10)	0.0052 (10)	0.0013 (10)
C10	0.0223 (12)	0.0342 (13)	0.0210 (12)	−0.0086 (10)	0.0034 (9)	−0.0025 (10)
C11	0.0181 (11)	0.0306 (12)	0.0188 (11)	−0.0078 (9)	0.0040 (9)	−0.0017 (10)
C12	0.0174 (11)	0.0303 (12)	0.0204 (12)	−0.0066 (9)	0.0009 (9)	−0.0003 (10)
C13	0.0163 (11)	0.0310 (12)	0.0201 (12)	−0.0071 (9)	0.0042 (9)	−0.0010 (10)
C14	0.0197 (12)	0.0358 (13)	0.0229 (12)	−0.0121 (10)	0.0015 (9)	−0.0007 (10)
C15	0.0201 (11)	0.0351 (13)	0.0224 (13)	−0.0083 (10)	−0.0025 (10)	−0.0006 (10)
C16	0.0183 (11)	0.0365 (13)	0.0208 (12)	−0.0074 (10)	−0.0006 (9)	0.0018 (10)
C17	0.0211 (12)	0.0403 (15)	0.0276 (14)	−0.0080 (11)	−0.0008 (10)	0.0057 (11)
C18	0.0205 (12)	0.0484 (17)	0.0293 (14)	−0.0048 (11)	0.0031 (10)	0.0120 (12)
C19	0.0228 (13)	0.0507 (17)	0.0218 (13)	0.0007 (12)	0.0019 (10)	0.0040 (12)
C20	0.0216 (12)	0.0405 (15)	0.0220 (13)	0.0002 (11)	−0.0009 (10)	0.0007 (11)
C21	0.0269 (13)	0.0474 (17)	0.0217 (13)	0.0027 (12)	−0.0036 (10)	−0.0064 (12)
C22	0.0346 (15)	0.0380 (15)	0.0288 (14)	−0.0008 (12)	−0.0082 (12)	−0.0079 (12)
C23	0.0271 (13)	0.0381 (15)	0.0242 (13)	−0.0069 (11)	−0.0036 (11)	−0.0028 (11)
C24	0.0213 (12)	0.0332 (13)	0.0212 (12)	−0.0068 (10)	−0.0016 (10)	−0.0035 (10)
C25	0.0174 (11)	0.0388 (14)	0.0214 (12)	−0.0045 (10)	−0.0017 (9)	−0.0006 (11)
C26	0.0189 (11)	0.0344 (13)	0.0207 (12)	−0.0074 (10)	−0.0019 (9)	−0.0010 (10)

Geometric parameters (Å, º) top

S1—C1	1.687 (3)	C6—H6	0.9500
S2—C14	1.685 (3)	C7—C8	1.411 (4)
O1—C2	1.210 (3)	C7—C12	1.423 (4)
O2—C13	1.216 (3)	C8—C9	1.374 (4)
O3—C15	1.210 (3)	C8—H8	0.9500
O4—C26	1.210 (3)	C9—C10	1.412 (4)
N1—N2	1.388 (3)	C9—H9	0.9500
N1—C13	1.413 (3)	C10—C11	1.374 (4)
N1—C2	1.417 (3)	C10—H10	0.9500
N2—C1	1.364 (3)	C11—C12	1.414 (3)
N2—H2	0.8800	C11—C13	1.475 (4)
N3—C1	1.324 (3)	C15—C16	1.469 (4)
N3—H31	0.8800	C16—C17	1.380 (4)
N3—H32	0.8800	C16—C25	1.413 (4)
N4—N5	1.399 (3)	C17—C18	1.400 (4)
N4—C15	1.412 (3)	C17—H17	0.9500
N4—C26	1.414 (3)	C18—C19	1.370 (5)
N5—C14	1.367 (3)	C18—H18	0.9500
N5—H5	0.8800	C19—C20	1.423 (4)
N6—C14	1.326 (4)	C19—H19	0.9500
N6—H61	0.8800	C20—C21	1.414 (4)
N6—H62	0.8800	C20—C25	1.422 (4)
C2—C3	1.466 (4)	C21—C22	1.372 (5)
C3—C4	1.381 (3)	C21—H21	0.9500
C3—C12	1.415 (4)	C22—C23	1.411 (4)
C4—C5	1.409 (4)	C22—H22	0.9500
C4—H4	0.9500	C23—C24	1.384 (4)
C5—C6	1.371 (4)	C23—H23	0.9500
C5—H5A	0.9500	C24—C25	1.415 (4)
C6—C7	1.421 (4)	C24—C26	1.480 (4)

N2—N1—C13	116.5 (2)	C10—C11—C12	121.2 (2)
N2—N1—C2	117.5 (2)	C10—C11—C13	118.6 (2)
C13—N1—C2	125.9 (2)	C12—C11—C13	120.1 (2)
C1—N2—N1	122.3 (2)	C11—C12—C3	121.7 (2)
C1—N2—H2	118.9	C11—C12—C7	118.8 (2)
N1—N2—H2	118.9	C3—C12—C7	119.4 (2)
C1—N3—H31	120.0	O2—C13—N1	120.4 (2)
C1—N3—H32	120.0	O2—C13—C11	123.9 (2)
H31—N3—H32	120.0	N1—C13—C11	115.7 (2)
N5—N4—C15	116.5 (2)	N6—C14—N5	118.8 (2)
N5—N4—C26	116.2 (2)	N6—C14—S2	123.1 (2)
C15—N4—C26	126.9 (2)	N5—C14—S2	118.0 (2)
C14—N5—N4	119.8 (2)	O3—C15—N4	118.9 (2)
C14—N5—H5	120.1	O3—C15—C16	124.9 (3)
N4—N5—H5	120.1	N4—C15—C16	116.2 (2)
C14—N6—H61	120.0	C17—C16—C25	121.2 (3)
C14—N6—H62	120.0	C17—C16—C15	119.2 (3)
H61—N6—H62	120.0	C25—C16—C15	119.7 (2)
N3—C1—N2	118.5 (2)	C16—C17—C18	119.9 (3)
N3—C1—S1	122.9 (2)	C16—C17—H17	120.1
N2—C1—S1	118.5 (2)	C18—C17—H17	120.1
O1—C2—N1	119.1 (2)	C19—C18—C17	120.7 (3)
O1—C2—C3	124.6 (2)	C19—C18—H18	119.7
N1—C2—C3	116.3 (2)	C17—C18—H18	119.7
C4—C3—C12	120.6 (2)	C18—C19—C20	120.8 (3)
C4—C3—C2	119.5 (2)	C18—C19—H19	119.6
C12—C3—C2	119.9 (2)	C20—C19—H19	119.6
C3—C4—C5	119.9 (3)	C21—C20—C25	118.8 (3)
C3—C4—H4	120.1	C21—C20—C19	122.5 (3)
C5—C4—H4	120.1	C25—C20—C19	118.7 (3)
C6—C5—C4	120.8 (2)	C22—C21—C20	121.1 (3)
C6—C5—H5A	119.6	C22—C21—H21	119.5
C4—C5—H5A	119.6	C20—C21—H21	119.5
C5—C6—C7	120.7 (3)	C21—C22—C23	120.3 (3)
C5—C6—H6	119.6	C21—C22—H22	119.8
C7—C6—H6	119.6	C23—C22—H22	119.8
C8—C7—C6	122.5 (2)	C24—C23—C22	120.0 (3)
C8—C7—C12	118.9 (2)	C24—C23—H23	120.0
C6—C7—C12	118.6 (2)	C22—C23—H23	120.0
C9—C8—C7	121.0 (2)	C23—C24—C25	120.4 (2)
C9—C8—H8	119.5	C23—C24—C26	119.0 (2)
C7—C8—H8	119.5	C25—C24—C26	120.6 (2)
C8—C9—C10	120.3 (2)	C16—C25—C24	121.8 (2)
C8—C9—H9	119.9	C16—C25—C20	118.8 (3)
C10—C9—H9	119.9	C24—C25—C20	119.4 (3)
C11—C10—C9	119.8 (2)	O4—C26—N4	120.4 (2)
C11—C10—H10	120.1	O4—C26—C24	125.1 (2)
C9—C10—H10	120.1	N4—C26—C24	114.5 (2)

C13—N1—N2—C1	−105.9 (3)	C10—C11—C13—N1	−176.4 (2)
C2—N1—N2—C1	78.2 (3)	C12—C11—C13—N1	6.3 (3)
C15—N4—N5—C14	77.9 (3)	N4—N5—C14—N6	11.6 (4)
C26—N4—N5—C14	−108.8 (3)	N4—N5—C14—S2	−171.95 (18)
N1—N2—C1—N3	5.9 (4)	N5—N4—C15—O3	−3.5 (4)
N1—N2—C1—S1	−177.69 (19)	C26—N4—C15—O3	−176.0 (2)
N2—N1—C2—O1	−8.2 (4)	N5—N4—C15—C16	176.8 (2)
C13—N1—C2—O1	176.4 (2)	C26—N4—C15—C16	4.3 (4)
N2—N1—C2—C3	173.1 (2)	O3—C15—C16—C17	−0.5 (4)
C13—N1—C2—C3	−2.4 (4)	N4—C15—C16—C17	179.2 (2)
O1—C2—C3—C4	5.2 (4)	O3—C15—C16—C25	−178.7 (3)
N1—C2—C3—C4	−176.2 (2)	N4—C15—C16—C25	1.0 (4)
O1—C2—C3—C12	−173.6 (2)	C25—C16—C17—C18	−0.3 (4)
N1—C2—C3—C12	5.1 (4)	C15—C16—C17—C18	−178.6 (3)
C12—C3—C4—C5	−0.3 (4)	C16—C17—C18—C19	−1.1 (4)
C2—C3—C4—C5	−179.0 (2)	C17—C18—C19—C20	1.5 (4)
C3—C4—C5—C6	0.3 (4)	C18—C19—C20—C21	179.2 (3)
C4—C5—C6—C7	0.1 (4)	C18—C19—C20—C25	−0.5 (4)
C5—C6—C7—C8	178.8 (2)	C25—C20—C21—C22	0.8 (4)
C5—C6—C7—C12	−0.5 (4)	C19—C20—C21—C22	−178.9 (3)
C6—C7—C8—C9	−179.7 (2)	C20—C21—C22—C23	−1.8 (5)
C12—C7—C8—C9	−0.4 (4)	C21—C22—C23—C24	1.0 (4)
C7—C8—C9—C10	−1.2 (4)	C22—C23—C24—C25	0.8 (4)
C8—C9—C10—C11	1.4 (4)	C22—C23—C24—C26	−177.7 (2)
C9—C10—C11—C12	0.1 (4)	C17—C16—C25—C24	179.7 (3)
C9—C10—C11—C13	−177.2 (2)	C15—C16—C25—C24	−2.1 (4)
C10—C11—C12—C3	179.0 (2)	C17—C16—C25—C20	1.4 (4)
C13—C11—C12—C3	−3.8 (4)	C15—C16—C25—C20	179.6 (2)
C10—C11—C12—C7	−1.7 (4)	C23—C24—C25—C16	179.9 (3)
C13—C11—C12—C7	175.5 (2)	C26—C24—C25—C16	−1.6 (4)
C4—C3—C12—C11	179.1 (2)	C23—C24—C25—C20	−1.8 (4)
C2—C3—C12—C11	−2.1 (4)	C26—C24—C25—C20	176.7 (2)
C4—C3—C12—C7	−0.2 (4)	C21—C20—C25—C16	179.4 (2)
C2—C3—C12—C7	178.6 (2)	C19—C20—C25—C16	−0.9 (4)
C8—C7—C12—C11	1.9 (4)	C21—C20—C25—C24	1.0 (4)
C6—C7—C12—C11	−178.8 (2)	C19—C20—C25—C24	−179.3 (3)
C8—C7—C12—C3	−178.8 (2)	N5—N4—C26—O4	−1.8 (4)
C6—C7—C12—C3	0.5 (4)	C15—N4—C26—O4	170.8 (3)
N2—N1—C13—O2	0.2 (4)	N5—N4—C26—C24	179.8 (2)
C2—N1—C13—O2	175.7 (2)	C15—N4—C26—C24	−7.7 (4)
N2—N1—C13—C11	−178.7 (2)	C23—C24—C26—O4	6.3 (4)
C2—N1—C13—C11	−3.2 (4)	C25—C24—C26—O4	−172.3 (3)
C10—C11—C13—O2	4.8 (4)	C23—C24—C26—N4	−175.4 (2)
C12—C11—C13—O2	−172.6 (2)	C25—C24—C26—N4	6.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.88	2.35	3.074 (3)	140
N2—H2···O1ⁱⁱ	0.88	2.33	2.993 (3)	132
N3—H31···O2ⁱⁱⁱ	0.88	2.09	2.912 (3)	154
N5—H5···O3ⁱⁱⁱ	0.88	2.55	3.301 (3)	144
N5—H5···O3^iv	0.88	2.52	2.988 (3)	114
N6—H61···O4ⁱ	0.88	2.21	3.015 (3)	152

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O₂S
M_r	271.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.5861 (2), 11.0475 (4), 22.5594 (9)
α, β, γ (°)	89.196 (3), 88.073 (3), 81.128 (3)
V (Å³)	1128.61 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.58
Crystal size (mm)	0.25 × 0.10 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.565, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	14869, 7974, 7060
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.196, 1.11
No. of reflections	7974
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.73

Computer programs: CrysAlis PRO (Agilent, 2012), 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
N2—H2···O1ⁱ	0.88	2.35	3.074 (3)	139.8
N2—H2···O1ⁱⁱ	0.88	2.33	2.993 (3)	131.9
N3—H31···O2ⁱⁱⁱ	0.88	2.09	2.912 (3)	154.4
N5—H5···O3ⁱⁱⁱ	0.88	2.55	3.301 (3)	144.3
N5—H5···O3^iv	0.88	2.52	2.988 (3)	114.3
N6—H61···O4ⁱ	0.88	2.21	3.015 (3)	152.2

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z.

Acknowledgements

We thank the Research Center of the College of Pharmacy College and Deanship of Scientific Research of King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Pessoa, C., Lotufo, L. V. C., de Moraes, M. O., Cavalcanti, S. M. T., Coêlho, L. C. D., Hernandes, M. Z., Leite, A. C. L., De Simone, C. A., Costa, V. M. A. & Souza, V. M. O. (2010). ChemMedChem, 5, 523–528. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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 68| Part 6| June 2012| Page o1811

doi:10.1107/S1600536812021812

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

N-[2,4-Dioxo-3-aza­tri­cyclo­[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-3-yl]thio­urea

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[2,4-Dioxo-3-azatricyclo[7.3.1.0^5,13]trideca-1(13),5,7,9,11-pentaen-3-yl]thiourea