Literature DB >> 21522446

3-(4-Bromo-phen-yl)-5-[4-(dimethyl-amino)-phen-yl]-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Hoong-Kun Fun, Thitipone Suwunwong, Suchada Chantrapromma.

Abstract

The mol-ecule of the title pyrazole derivative, C(18)H(19)BrN(4)S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromo-phenyl ring, whereas it is inclined to the 4-(dimethyl-amino)-phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethyl-amino group is slightly twisted from the attached benzene ring [C-C-N-C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, mol-ecules are linked by inter-molecular N-H⋯S hydrogen bonds into chains along [20]. The crystal is further stabilized by C-H⋯π inter-actions.

Entities: CellLine Chemical Disease Species

Year: 2011 PMID： 21522446 PMCID： PMC3052174 DOI： 10.1107/S1600536811006106

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

Related literature

For background to chalcone synthesis and the biological activity of pyrazole derivatives, see: Bekhit et al. (2008 ▶); Ono et al. (2007 ▶); Cottineau et al. (2002 ▶); Gadakh et al. (2010 ▶); Hall et al. (2008 ▶); Hoepping et al. (2007 ▶); Mikhaylichenko et al. (2009 ▶); Park et al. (2005 ▶) Souza et al. (2002 ▶); Xie et al. (2008 ▶). For related structures, see; Chantrapromma et al. (2009 ▶); Suwunwong et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H19BrN4S M = 403.34 Triclinic, a = 6.9153 (1) Å b = 9.5122 (1) Å c = 15.1545 (2) Å α = 72.196 (1)° β = 80.941 (1)° γ = 69.845 (1)° V = 889.48 (2) Å3 Z = 2 Mo Kα radiation μ = 2.44 mm−1 T = 100 K 0.55 × 0.32 × 0.31 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.349, T max = 0.520 28456 measured reflections 7823 independent reflections 6784 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.073 S = 1.05 7823 reflections 227 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.96 e Å−3 Δρmin = −0.50 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006106/rz2558sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006106/rz2558Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₉BrN₄S	Z = 2
M_r = 403.34	F(000) = 412
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Melting point = 481–482 K
a = 6.9153 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5122 (1) Å	Cell parameters from 7823 reflections
c = 15.1545 (2) Å	θ = 2.4–35.1°
α = 72.196 (1)°	µ = 2.44 mm⁻¹
β = 80.941 (1)°	T = 100 K
γ = 69.845 (1)°	Block, pale yellow
V = 889.48 (2) Å³	0.55 × 0.32 × 0.31 mm

Bruker APEXII CCD area-detector diffractometer	7823 independent reflections
Radiation source: sealed tube	6784 reflections with I > 2σ(I)
graphite	R_int = 0.023
φ and ω scans	θ_max = 35.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→10
T_min = 0.349, T_max = 0.520	k = −15→15
28456 measured reflections	l = −24→24

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0344P)² + 0.3232P] where P = (F_o² + 2F_c²)/3
7823 reflections	(Δ/σ)_max = 0.003
227 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	1.641401 (17)	−0.173962 (13)	0.169443 (10)	0.02713 (4)
S1	0.08981 (4)	0.61386 (3)	0.083129 (18)	0.01668 (5)
N1	0.62104 (13)	0.27982 (10)	0.13070 (6)	0.01465 (14)
N2	0.44511 (13)	0.40189 (10)	0.14121 (6)	0.01404 (14)
N3	−0.0497 (2)	0.25372 (15)	0.52890 (9)	0.0346 (3)
N4	0.31575 (15)	0.37031 (12)	0.02111 (7)	0.01857 (16)
C1	1.02110 (17)	0.05782 (12)	0.12650 (8)	0.01819 (18)
H1A	0.9213	0.0544	0.0933	0.022*
C2	1.21950 (17)	−0.04510 (13)	0.12460 (9)	0.02047 (19)
H2A	1.2534	−0.1179	0.0908	0.025*
C3	1.36736 (16)	−0.03752 (12)	0.17431 (8)	0.01850 (18)
C4	1.32036 (16)	0.06853 (12)	0.22612 (8)	0.01758 (18)
H4A	1.4208	0.0711	0.2593	0.021*
C5	1.12052 (15)	0.17132 (12)	0.22782 (7)	0.01604 (17)
H5A	1.0873	0.2432	0.2623	0.019*
C6	0.96924 (15)	0.16730 (11)	0.17801 (7)	0.01418 (16)
C7	0.76209 (15)	0.27851 (11)	0.17797 (7)	0.01395 (15)
C8	0.69425 (15)	0.40713 (12)	0.22566 (7)	0.01553 (16)
H8A	0.7585	0.4870	0.1952	0.019*
H8B	0.7266	0.3671	0.2904	0.019*
C9	0.45956 (15)	0.47007 (11)	0.21552 (7)	0.01428 (16)
H9A	0.4135	0.5839	0.1937	0.017*
C10	0.33157 (15)	0.41586 (12)	0.30181 (7)	0.01506 (16)
C11	0.40552 (17)	0.27201 (13)	0.36660 (8)	0.01809 (18)
H11A	0.5411	0.2104	0.3590	0.022*
C12	0.28225 (18)	0.21843 (14)	0.44205 (8)	0.0221 (2)
H12A	0.3371	0.1226	0.4842	0.027*
C13	0.07487 (19)	0.30739 (14)	0.45555 (8)	0.0219 (2)
C14	0.00187 (17)	0.45394 (14)	0.39134 (8)	0.01970 (19)
H14A	−0.1332	0.5167	0.3988	0.024*
C15	0.12813 (16)	0.50602 (13)	0.31725 (7)	0.01712 (17)
H15A	0.0761	0.6039	0.2765	0.021*
C16	−0.2680 (2)	0.3366 (2)	0.53468 (10)	0.0324 (3)
H16A	−0.3276	0.3493	0.4785	0.049*
H16B	−0.2880	0.4370	0.5428	0.049*
H16C	−0.3334	0.2786	0.5866	0.049*
C17	0.0361 (3)	0.1144 (2)	0.60089 (12)	0.0443 (4)
H17A	0.1564	0.1203	0.6219	0.067*
H17B	0.0737	0.0256	0.5768	0.067*
H17C	−0.0645	0.1046	0.6519	0.067*
C18	0.29283 (15)	0.45225 (12)	0.08212 (7)	0.01415 (16)
H1N4	0.211 (3)	0.386 (2)	−0.0067 (13)	0.028 (4)*
H2N4	0.414 (3)	0.287 (2)	0.0245 (12)	0.027 (4)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01316 (5)	0.01906 (5)	0.05023 (9)	−0.00079 (4)	−0.00226 (5)	−0.01560 (5)
S1	0.01295 (10)	0.01764 (10)	0.01829 (11)	−0.00210 (8)	−0.00309 (8)	−0.00530 (8)
N1	0.0112 (3)	0.0157 (3)	0.0161 (4)	−0.0029 (3)	−0.0005 (3)	−0.0046 (3)
N2	0.0112 (3)	0.0159 (3)	0.0149 (3)	−0.0024 (3)	−0.0014 (3)	−0.0059 (3)
N3	0.0276 (6)	0.0347 (6)	0.0316 (6)	−0.0095 (5)	0.0114 (5)	−0.0020 (5)
N4	0.0150 (4)	0.0224 (4)	0.0189 (4)	−0.0026 (3)	−0.0039 (3)	−0.0088 (3)
C1	0.0155 (4)	0.0180 (4)	0.0224 (5)	−0.0042 (3)	−0.0027 (3)	−0.0078 (4)
C2	0.0165 (4)	0.0178 (4)	0.0284 (5)	−0.0035 (3)	−0.0014 (4)	−0.0102 (4)
C3	0.0125 (4)	0.0140 (4)	0.0282 (5)	−0.0032 (3)	−0.0008 (3)	−0.0060 (4)
C4	0.0128 (4)	0.0158 (4)	0.0251 (5)	−0.0044 (3)	−0.0029 (3)	−0.0061 (4)
C5	0.0131 (4)	0.0150 (4)	0.0210 (4)	−0.0046 (3)	−0.0012 (3)	−0.0060 (3)
C6	0.0112 (4)	0.0140 (4)	0.0170 (4)	−0.0044 (3)	−0.0005 (3)	−0.0034 (3)
C7	0.0120 (4)	0.0142 (4)	0.0153 (4)	−0.0043 (3)	−0.0001 (3)	−0.0035 (3)
C8	0.0122 (4)	0.0167 (4)	0.0194 (4)	−0.0043 (3)	−0.0012 (3)	−0.0073 (3)
C9	0.0124 (4)	0.0153 (4)	0.0164 (4)	−0.0046 (3)	−0.0016 (3)	−0.0055 (3)
C10	0.0133 (4)	0.0168 (4)	0.0161 (4)	−0.0038 (3)	−0.0011 (3)	−0.0068 (3)
C11	0.0154 (4)	0.0189 (4)	0.0185 (4)	−0.0033 (3)	0.0000 (3)	−0.0059 (3)
C12	0.0207 (5)	0.0216 (5)	0.0194 (5)	−0.0046 (4)	0.0007 (4)	−0.0023 (4)
C13	0.0208 (5)	0.0256 (5)	0.0199 (5)	−0.0086 (4)	0.0040 (4)	−0.0078 (4)
C14	0.0147 (4)	0.0244 (5)	0.0204 (5)	−0.0041 (4)	0.0008 (3)	−0.0100 (4)
C15	0.0142 (4)	0.0195 (4)	0.0173 (4)	−0.0027 (3)	−0.0017 (3)	−0.0072 (3)
C16	0.0234 (6)	0.0522 (9)	0.0273 (6)	−0.0184 (6)	0.0087 (5)	−0.0162 (6)
C17	0.0419 (9)	0.0417 (8)	0.0351 (8)	−0.0142 (7)	0.0126 (7)	0.0035 (6)
C18	0.0124 (4)	0.0167 (4)	0.0131 (4)	−0.0051 (3)	−0.0005 (3)	−0.0032 (3)

Br1—C3	1.8976 (10)	C7—C8	1.5091 (14)
S1—C18	1.6896 (10)	C8—C9	1.5391 (14)
N1—C7	1.2927 (13)	C8—H8A	0.9700
N1—N2	1.3901 (12)	C8—H8B	0.9700
N2—C18	1.3518 (13)	C9—C10	1.5155 (14)
N2—C9	1.4917 (13)	C9—H9A	0.9800
N3—C13	1.3759 (16)	C10—C11	1.3972 (15)
N3—C17	1.441 (2)	C10—C15	1.3990 (14)
N3—C16	1.4450 (19)	C11—C12	1.3893 (16)
N4—C18	1.3404 (14)	C11—H11A	0.9300
N4—H1N4	0.842 (19)	C12—C13	1.4113 (17)
N4—H2N4	0.841 (19)	C12—H12A	0.9300
C1—C2	1.3859 (15)	C13—C14	1.4090 (17)
C1—C6	1.4049 (15)	C14—C15	1.3848 (16)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3945 (16)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3848 (15)	C16—H16B	0.9600
C4—C5	1.3926 (14)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3999 (14)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.4583 (14)

C7—N1—N2	107.84 (8)	N2—C9—C8	100.12 (8)
C18—N2—N1	119.42 (8)	C10—C9—C8	114.94 (8)
C18—N2—C9	127.78 (8)	N2—C9—H9A	110.4
N1—N2—C9	112.61 (8)	C10—C9—H9A	110.4
C13—N3—C17	120.35 (12)	C8—C9—H9A	110.4
C13—N3—C16	120.36 (12)	C11—C10—C15	117.01 (10)
C17—N3—C16	119.29 (12)	C11—C10—C9	122.25 (9)
C18—N4—H1N4	117.0 (13)	C15—C10—C9	120.66 (9)
C18—N4—H2N4	120.0 (12)	C12—C11—C10	121.88 (10)
H1N4—N4—H2N4	119.5 (17)	C12—C11—H11A	119.1
C2—C1—C6	120.68 (10)	C10—C11—H11A	119.1
C2—C1—H1A	119.7	C11—C12—C13	120.90 (10)
C6—C1—H1A	119.7	C11—C12—H12A	119.6
C1—C2—C3	118.82 (10)	C13—C12—H12A	119.6
C1—C2—H2A	120.6	N3—C13—C14	121.54 (11)
C3—C2—H2A	120.6	N3—C13—C12	121.30 (11)
C4—C3—C2	121.77 (10)	C14—C13—C12	117.15 (10)
C4—C3—Br1	119.03 (8)	C15—C14—C13	121.01 (10)
C2—C3—Br1	119.19 (8)	C15—C14—H14A	119.5
C3—C4—C5	119.05 (10)	C13—C14—H14A	119.5
C3—C4—H4A	120.5	C14—C15—C10	122.00 (10)
C5—C4—H4A	120.5	C14—C15—H15A	119.0
C4—C5—C6	120.47 (10)	C10—C15—H15A	119.0
C4—C5—H5A	119.8	N3—C16—H16A	109.5
C6—C5—H5A	119.8	N3—C16—H16B	109.5
C5—C6—C1	119.21 (9)	H16A—C16—H16B	109.5
C5—C6—C7	120.05 (9)	N3—C16—H16C	109.5
C1—C6—C7	120.72 (9)	H16A—C16—H16C	109.5
N1—C7—C6	121.29 (9)	H16B—C16—H16C	109.5
N1—C7—C8	113.61 (8)	N3—C17—H17A	109.5
C6—C7—C8	124.98 (9)	N3—C17—H17B	109.5
C7—C8—C9	102.52 (8)	H17A—C17—H17B	109.5
C7—C8—H8A	111.3	N3—C17—H17C	109.5
C9—C8—H8A	111.3	H17A—C17—H17C	109.5
C7—C8—H8B	111.3	H17B—C17—H17C	109.5
C9—C8—H8B	111.3	N4—C18—N2	116.40 (9)
H8A—C8—H8B	109.2	N4—C18—S1	122.21 (8)
N2—C9—C10	110.17 (8)	N2—C18—S1	121.35 (8)

C7—N1—N2—C18	164.20 (9)	C7—C8—C9—N2	−16.35 (9)
C7—N1—N2—C9	−11.12 (11)	C7—C8—C9—C10	101.64 (9)
C6—C1—C2—C3	−0.38 (17)	N2—C9—C10—C11	82.45 (11)
C1—C2—C3—C4	0.78 (18)	C8—C9—C10—C11	−29.71 (13)
C1—C2—C3—Br1	−178.27 (9)	N2—C9—C10—C15	−94.19 (11)
C2—C3—C4—C5	−0.65 (17)	C8—C9—C10—C15	153.64 (9)
Br1—C3—C4—C5	178.40 (8)	C15—C10—C11—C12	1.39 (16)
C3—C4—C5—C6	0.12 (16)	C9—C10—C11—C12	−175.37 (10)
C4—C5—C6—C1	0.25 (16)	C10—C11—C12—C13	0.81 (18)
C4—C5—C6—C7	−178.15 (10)	C17—N3—C13—C14	−170.94 (15)
C2—C1—C6—C5	−0.12 (16)	C16—N3—C13—C14	8.9 (2)
C2—C1—C6—C7	178.27 (10)	C17—N3—C13—C12	8.4 (2)
N2—N1—C7—C6	−177.42 (9)	C16—N3—C13—C12	−171.79 (13)
N2—N1—C7—C8	−1.24 (11)	C11—C12—C13—N3	178.51 (13)
C5—C6—C7—N1	178.25 (10)	C11—C12—C13—C14	−2.16 (18)
C1—C6—C7—N1	−0.12 (15)	N3—C13—C14—C15	−179.34 (12)
C5—C6—C7—C8	2.53 (15)	C12—C13—C14—C15	1.33 (17)
C1—C6—C7—C8	−175.85 (10)	C13—C14—C15—C10	0.88 (17)
N1—C7—C8—C9	12.11 (11)	C11—C10—C15—C14	−2.23 (16)
C6—C7—C8—C9	−171.88 (9)	C9—C10—C15—C14	174.59 (10)
C18—N2—C9—C10	81.36 (12)	N1—N2—C18—N4	5.51 (14)
N1—N2—C9—C10	−103.80 (9)	C9—N2—C18—N4	−179.96 (9)
C18—N2—C9—C8	−157.18 (10)	N1—N2—C18—S1	−172.28 (7)
N1—N2—C9—C8	17.65 (10)	C9—N2—C18—S1	2.25 (15)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···S1ⁱ	0.84 (2)	2.54 (2)	3.3679 (11)	170.8 (17)
C5—H5A···Cg2ⁱⁱ	0.93	2.72	3.5462 (12)	149
C16—H16B···Cg2ⁱⁱⁱ	0.96	2.71	3.6676 (18)	154
C17—H17C···Cg1^iv	0.96	2.74	3.5990 (19)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯S1ⁱ	0.84 (2)	2.54 (2)	3.3679 (11)	170.8 (17)
C5—H5A⋯Cg2ⁱⁱ	0.93	2.72	3.5462 (12)	149
C16—H16B⋯Cg2ⁱⁱⁱ	0.96	2.71	3.6676 (18)	154
C17—H17C⋯Cg1^iv	0.96	2.74	3.5990 (19)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

12 in total

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Journal: Bioorg Med Chem Lett Date: 2010-08-17 Impact factor: 2.823

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Authors: Alexander Hoepping; Matthias Scheunemann; Steffen Fischer; Winnie Deuther-Conrad; Achim Hiller; Florian Wegner; Michael Diekers; Jörg Steinbach; Peter Brust
Journal: Nucl Med Biol Date: 2007-06-08 Impact factor: 2.408

4. Non-acidic pyrazole EP1 receptor antagonists with in vivo analgesic efficacy.

Authors: Adrian Hall; Andy Billinton; Susan H Brown; Nicholas M Clayton; Anita Chowdhury; Gerard M P Giblin; Paul Goldsmith; Thomas G Hayhow; David N Hurst; Ian R Kilford; Alan Naylor; Barry Passingham; Lisa Winyard
Journal: Bioorg Med Chem Lett Date: 2008-04-11 Impact factor: 2.823

5. Identification of antitumor activity of pyrazole oxime ethers.

Authors: Hyun-Ja Park; Kyung Lee; Su-Jin Park; Bangle Ahn; Jong-Cheol Lee; Heeyeong Cho; Kee-In Lee
Journal: Bioorg Med Chem Lett Date: 2005-07-01 Impact factor: 2.823

6. Hypothermic and antipyretic effects of 3-methyl- and 3-phenyl-5-hydroxy-5-trichloromethyl-4,5-dihydro-1H-pyrazole-1-carboxyamides in mice.

Authors: Fabiane R Souza; Vanessa T Souza; Viviane Ratzlaff; Lysandro P Borges; Marlí R Oliveira; Helio G Bonacorso; Nilo Zanatta; Marcos A P Martins; Carlos F Mello
Journal: Eur J Pharmacol Date: 2002-09-13 Impact factor: 4.432

7. Novel chalcones as probes for in vivo imaging of beta-amyloid plaques in Alzheimer's brains.

Authors: Masahiro Ono; Mamoru Haratake; Hiroshi Mori; Morio Nakayama
Journal: Bioorg Med Chem Date: 2007-08-21 Impact factor: 3.641

8. (E)-1-(4-Bromo-phen-yl)-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Authors: Suchada Chantrapromma; Thitipone Suwunwong; Chatchanok Karalai; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-03-28

9. (E)-1-(4-Bromo-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Authors: Thitipone Suwunwong; Suchada Chantrapromma; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-12-13

10. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

4 in total

1. Dimethyl 1-(4-methyl-phen-yl)-8-(thio-phen-2-yl)-11-oxatricyclo-[6.2.1.0(2,7)]undeca-2,4,6,9-tetra-ene-9,10-dicarboxy-late.

Authors: B Balakrishnan; Meganathan Nandakumar; Pandamangalam R Seshadri; Arasambattu K Mohanakrishnan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-03-06