4-(4-Chloro­phen­yl)-5-[2-methyl-1-(4-methyl­phen­yl)-2-nitro­prop­yl]-1,2,3-selenadiazole

Gunasekaran, B.; Manivannan, V.; Saravanan, S.; Muthusubramanian, S.; Nethaji, M.

doi:10.1107/S1600536807043553

Buy article online - an online subscription or single-article purchase is required to access this article.

4-(4-Chlorophenyl)-5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-1,2,3-selenadiazole

B. Gunasekaran, V. Manivannan, S. Saravanan, S. Muthusubramanian and M. Nethaji

In the title compound, C₁₉H₁₈ClN₃O₂Se, the heterocyclic ring makes dihedral angles of 40.74 (12) and 51.76 (11)° with the chlorophenyl and methylphenyl rings, respectively. The molecular structure is stabilized by weak intramolecular C—H

Se and C—H

O interactions, and the crystal packing is stabilized by weak intermolecular C—H

O interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043553/bt2479sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043553/bt2479Isup2.hkl Contains datablock I

CCDC reference: 663740

checkCIF report

Key indicators

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.102
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.35
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT322_ALERT_2_C Check Hybridisation of  Se1    in Main Residue .          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Selenium containing compounds like 1,2,3-selenadiazole possess various beneficial activities like antifungal (Kuroda et al., 2001), antibacterial (El-Kashef et al., 1986), antimicrobial (El-Bahaie et al., 1990) and insecticidal (Padmavathi et al., 2002) activities. As naturally occurring nitro compounds exhibit broad antibiotic activity and certain alkyl nitro compounds exhibit antitumor activity, it was decided to synthesize and structurally characterize a set of 1,2,3-selenadiazoles with nitro group in the side chain (Saravanan et al., 2006).

The geometric parameters in the compound agree with the reported values of similar structures (Mellini & Merlino, 1976a; Mellini & Merlino, 1976b; Bertini et al., 1984). The Chlorophenyl ring makes a dihedral angle of 40.74 (12) ° with the heterocyclic ring. The methylphenyl ring makes a dihedral angle of 51.76 (11) ° with the heterocyclic ring (Fig 1.).

The molecular structure is stabilized by weak intramolecular C—H···Se and C—H···O interactions and the crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For related literature, see: Mellini & Merlino (1976a,b); Bertini et al. (1984); El-Bahaie et al. (1990); El-Kashef et al. (1986); Kuroda et al. (2001); Padmavathi et al. (2002); Saravanan et al. (2006).

Experimental top

A solution of 0.005 mole of 2-[(E)-1-(4-chlorophenyl)-4-methyl-3-(4- methylphenyl)-4-nitropentylidene]-1-hydrazinecarboxamide and 0.05 mole of powdered selenium dioxide in dry THF was gently heated on a water bath for two hours. The selenium deposited on cooling was removed by filtration, and the filtrate was poured into crushed ice, extracted with chloroform, and purified by column chromatography using silica gel (60–120 mesh) with 97:3 petroleum ether: ethyl acetate as eluent to give the title compound, which were recrystallized from ethyl alcohol.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

4-(4-Chlorophenyl)-5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-1,2,3- selenadiazole top

Crystal data top

C₁₉H₁₈ClN₃O₂Se	F(000) = 880
M_r = 434.77	D_x = 1.516 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 134 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.346 (3) Å	θ = 2.5–26.5°
b = 9.636 (2) Å	µ = 2.13 mm⁻¹
c = 14.887 (3) Å	T = 290 K
β = 95.668 (4)°	Rectangular, colourless
V = 1905.1 (7) Å³	0.35 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3884 independent reflections
Radiation source: fine-focus seald tube	2618 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scan	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.527, T_max = 0.651	k = −12→11
14877 measured reflections	l = −17→18

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0451P)² + 0.4482P] where P = (F_o² + 2F_c²)/3
3884 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₈ClN₃O₂Se	V = 1905.1 (7) Å³
M_r = 434.77	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.346 (3) Å	µ = 2.13 mm⁻¹
b = 9.636 (2) Å	T = 290 K
c = 14.887 (3) Å	0.35 × 0.25 × 0.22 mm
β = 95.668 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3884 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2618 reflections with I > 2σ(I)
T_min = 0.527, T_max = 0.651	R_int = 0.048
14877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.01	Δρ_max = 0.54 e Å⁻³
3884 reflections	Δρ_min = −0.23 e Å⁻³
237 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 > 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.

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

	x	y	z	U_iso*/U_eq
Se1	0.28743 (3)	0.19923 (4)	0.15518 (2)	0.05775 (16)
C3	0.4001 (2)	0.2992 (3)	0.32749 (19)	0.0354 (7)
H3	0.4552	0.3649	0.3427	0.042*
Cl1	0.73325 (7)	0.83606 (10)	0.26746 (7)	0.0688 (3)
C2	0.3746 (2)	0.3123 (3)	0.2263 (2)	0.0391 (7)
N3	0.4788 (2)	0.1728 (3)	0.45710 (19)	0.0487 (7)
N1	0.3193 (2)	0.3034 (4)	0.05636 (18)	0.0636 (9)
C7	0.3166 (2)	0.3435 (3)	0.38403 (19)	0.0345 (7)
O1	0.4309 (2)	0.1161 (3)	0.51175 (16)	0.0681 (8)
C17	0.6391 (2)	0.7137 (3)	0.2389 (2)	0.0451 (8)
C8	0.3411 (2)	0.4283 (3)	0.4583 (2)	0.0431 (8)
H8	0.4056	0.4655	0.4679	0.052*
C12	0.2184 (2)	0.2959 (4)	0.3705 (2)	0.0469 (8)
H12	0.1986	0.2429	0.3197	0.056*
C14	0.4913 (2)	0.5163 (3)	0.1966 (2)	0.0377 (7)
C1	0.4149 (2)	0.4079 (3)	0.17203 (19)	0.0406 (8)
C15	0.5673 (2)	0.5389 (3)	0.1404 (2)	0.0439 (8)
H15	0.5684	0.4867	0.0880	0.053*
C18	0.5641 (3)	0.6962 (3)	0.2950 (2)	0.0463 (8)
H18	0.5632	0.7495	0.3471	0.056*
N2	0.3820 (2)	0.3981 (3)	0.08075 (18)	0.0549 (8)
C9	0.2712 (3)	0.4583 (4)	0.5183 (2)	0.0519 (9)
H9	0.2897	0.5155	0.5675	0.062*
C16	0.6408 (2)	0.6376 (4)	0.1614 (2)	0.0480 (8)
H16	0.6910	0.6524	0.1233	0.058*
O2	0.5502 (2)	0.2477 (3)	0.4770 (2)	0.0834 (9)
C19	0.4901 (2)	0.5986 (3)	0.2731 (2)	0.0431 (8)
H19	0.4385	0.5876	0.3101	0.052*
C4	0.4443 (2)	0.1525 (3)	0.3560 (2)	0.0400 (8)
C10	0.1748 (3)	0.4054 (4)	0.5069 (2)	0.0542 (9)
C5	0.3720 (3)	0.0321 (3)	0.3480 (2)	0.0589 (10)
H5A	0.3516	0.0142	0.2854	0.088*
H5B	0.3140	0.0541	0.3785	0.088*
H5C	0.4045	−0.0488	0.3750	0.088*
C6	0.5383 (3)	0.1222 (5)	0.3094 (3)	0.0729 (12)
H6A	0.5718	0.0422	0.3365	0.109*
H6B	0.5827	0.2007	0.3157	0.109*
H6C	0.5196	0.1046	0.2465	0.109*
C11	0.1494 (3)	0.3253 (4)	0.4309 (3)	0.0581 (10)
H11	0.0843	0.2906	0.4203	0.070*
C13	0.1020 (3)	0.4306 (5)	0.5764 (3)	0.0898 (15)
H13A	0.1286	0.3914	0.6331	0.135*
H13B	0.0386	0.3878	0.5571	0.135*
H13C	0.0925	0.5286	0.5834	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0682 (3)	0.0690 (3)	0.0356 (2)	−0.0224 (2)	0.00294 (16)	−0.00654 (18)
C3	0.0380 (17)	0.0384 (17)	0.0303 (16)	−0.0051 (14)	0.0064 (13)	0.0013 (14)
Cl1	0.0588 (6)	0.0648 (7)	0.0821 (7)	−0.0143 (5)	0.0038 (5)	−0.0075 (5)
C2	0.0413 (17)	0.0449 (19)	0.0322 (17)	−0.0011 (15)	0.0095 (13)	−0.0007 (14)
N3	0.064 (2)	0.0423 (18)	0.0390 (17)	0.0131 (15)	0.0004 (15)	0.0019 (13)
N1	0.076 (2)	0.084 (2)	0.0303 (16)	−0.0160 (19)	0.0026 (15)	−0.0032 (16)
C7	0.0420 (18)	0.0334 (17)	0.0283 (16)	0.0032 (13)	0.0040 (13)	0.0000 (12)
O1	0.106 (2)	0.0651 (18)	0.0368 (14)	0.0214 (16)	0.0236 (14)	0.0095 (13)
C17	0.0432 (19)	0.045 (2)	0.046 (2)	0.0017 (15)	0.0030 (16)	0.0058 (16)
C8	0.0483 (19)	0.045 (2)	0.0351 (18)	0.0027 (16)	0.0013 (15)	−0.0020 (15)
C12	0.049 (2)	0.054 (2)	0.0390 (18)	−0.0033 (17)	0.0091 (16)	−0.0097 (16)
C14	0.0444 (18)	0.0392 (18)	0.0300 (17)	0.0035 (14)	0.0057 (14)	0.0055 (14)
C1	0.0456 (18)	0.051 (2)	0.0261 (17)	0.0020 (16)	0.0077 (14)	0.0015 (14)
C15	0.0494 (19)	0.052 (2)	0.0313 (18)	0.0017 (16)	0.0100 (15)	−0.0002 (15)
C18	0.060 (2)	0.043 (2)	0.0371 (18)	0.0053 (17)	0.0086 (16)	−0.0015 (15)
N2	0.0635 (19)	0.070 (2)	0.0320 (16)	−0.0083 (17)	0.0073 (14)	−0.0013 (14)
C9	0.067 (2)	0.058 (2)	0.0300 (18)	0.0177 (19)	0.0003 (17)	−0.0061 (16)
C16	0.047 (2)	0.059 (2)	0.041 (2)	0.0017 (17)	0.0147 (16)	0.0068 (17)
O2	0.081 (2)	0.077 (2)	0.084 (2)	−0.0086 (17)	−0.0328 (17)	−0.0016 (17)
C19	0.050 (2)	0.044 (2)	0.0379 (19)	0.0038 (16)	0.0158 (15)	0.0049 (15)
C4	0.0491 (19)	0.0430 (19)	0.0292 (17)	0.0025 (15)	0.0104 (14)	−0.0019 (13)
C10	0.058 (2)	0.069 (3)	0.037 (2)	0.019 (2)	0.0139 (17)	0.0045 (18)
C5	0.078 (3)	0.042 (2)	0.055 (2)	−0.0044 (19)	0.000 (2)	−0.0013 (17)
C6	0.075 (3)	0.080 (3)	0.070 (3)	0.029 (2)	0.037 (2)	0.011 (2)
C11	0.044 (2)	0.074 (3)	0.058 (2)	0.0010 (18)	0.0143 (18)	−0.004 (2)
C13	0.082 (3)	0.139 (4)	0.053 (3)	0.039 (3)	0.030 (2)	0.001 (3)

Geometric parameters (Å, º) top

Se1—C2	1.849 (3)	C1—N2	1.389 (4)
Se1—N1	1.865 (3)	C15—C16	1.381 (4)
C3—C2	1.517 (4)	C15—H15	0.9300
C3—C7	1.522 (4)	C18—C19	1.379 (4)
C3—C4	1.573 (4)	C18—H18	0.9300
C3—H3	0.9800	C9—C10	1.378 (5)
Cl1—C17	1.745 (3)	C9—H9	0.9300
C2—C1	1.370 (4)	C16—H16	0.9300
N3—O2	1.209 (4)	C19—H19	0.9300
N3—O1	1.213 (4)	C4—C5	1.507 (4)
N3—C4	1.543 (4)	C4—C6	1.520 (4)
N1—N2	1.266 (4)	C10—C11	1.383 (5)
C7—C12	1.384 (4)	C10—C13	1.508 (5)
C7—C8	1.387 (4)	C5—H5A	0.9600
C17—C16	1.369 (5)	C5—H5B	0.9600
C17—C18	1.376 (4)	C5—H5C	0.9600
C8—C9	1.386 (4)	C6—H6A	0.9600
C8—H8	0.9300	C6—H6B	0.9600
C12—C11	1.379 (4)	C6—H6C	0.9600
C12—H12	0.9300	C11—H11	0.9300
C14—C19	1.388 (4)	C13—H13A	0.9600
C14—C15	1.393 (4)	C13—H13B	0.9600
C14—C1	1.481 (4)	C13—H13C	0.9600

C2—Se1—N1	87.39 (13)	C10—C9—C8	121.5 (3)
C2—C3—C7	114.9 (2)	C10—C9—H9	119.2
C2—C3—C4	112.6 (2)	C8—C9—H9	119.2
C7—C3—C4	112.3 (2)	C17—C16—C15	119.3 (3)
C2—C3—H3	105.4	C17—C16—H16	120.4
C7—C3—H3	105.4	C15—C16—H16	120.4
C4—C3—H3	105.4	C18—C19—C14	121.2 (3)
C1—C2—C3	125.4 (3)	C18—C19—H19	119.4
C1—C2—Se1	108.7 (2)	C14—C19—H19	119.4
C3—C2—Se1	125.9 (2)	C5—C4—C6	111.5 (3)
O2—N3—O1	124.0 (3)	C5—C4—N3	107.5 (3)
O2—N3—C4	117.8 (3)	C6—C4—N3	106.8 (3)
O1—N3—C4	118.1 (3)	C5—C4—C3	116.7 (3)
N2—N1—Se1	110.9 (2)	C6—C4—C3	110.8 (3)
C12—C7—C8	117.2 (3)	N3—C4—C3	102.5 (2)
C12—C7—C3	124.1 (3)	C9—C10—C11	117.3 (3)
C8—C7—C3	118.5 (3)	C9—C10—C13	120.8 (4)
C16—C17—C18	121.3 (3)	C11—C10—C13	121.9 (4)
C16—C17—Cl1	119.7 (3)	C4—C5—H5A	109.5
C18—C17—Cl1	119.0 (3)	C4—C5—H5B	109.5
C9—C8—C7	121.1 (3)	H5A—C5—H5B	109.5
C9—C8—H8	119.5	C4—C5—H5C	109.5
C7—C8—H8	119.5	H5A—C5—H5C	109.5
C11—C12—C7	121.4 (3)	H5B—C5—H5C	109.5
C11—C12—H12	119.3	C4—C6—H6A	109.5
C7—C12—H12	119.3	C4—C6—H6B	109.5
C19—C14—C15	118.1 (3)	H6A—C6—H6B	109.5
C19—C14—C1	122.8 (3)	C4—C6—H6C	109.5
C15—C14—C1	119.1 (3)	H6A—C6—H6C	109.5
C2—C1—N2	115.2 (3)	H6B—C6—H6C	109.5
C2—C1—C14	129.1 (3)	C12—C11—C10	121.5 (3)
N2—C1—C14	115.7 (3)	C12—C11—H11	119.3
C16—C15—C14	121.0 (3)	C10—C11—H11	119.3
C16—C15—H15	119.5	C10—C13—H13A	109.5
C14—C15—H15	119.5	C10—C13—H13B	109.5
C17—C18—C19	119.1 (3)	H13A—C13—H13B	109.5
C17—C18—H18	120.5	C10—C13—H13C	109.5
C19—C18—H18	120.5	H13A—C13—H13C	109.5
N1—N2—C1	117.8 (3)	H13B—C13—H13C	109.5

C7—C3—C2—C1	109.3 (3)	Se1—N1—N2—C1	0.1 (4)
C4—C3—C2—C1	−120.5 (3)	C2—C1—N2—N1	−0.2 (5)
C7—C3—C2—Se1	−72.7 (3)	C14—C1—N2—N1	177.5 (3)
C4—C3—C2—Se1	57.5 (3)	C7—C8—C9—C10	0.0 (5)
N1—Se1—C2—C1	−0.1 (2)	C18—C17—C16—C15	−1.7 (5)
N1—Se1—C2—C3	−178.4 (3)	Cl1—C17—C16—C15	178.6 (2)
C2—Se1—N1—N2	0.0 (3)	C14—C15—C16—C17	0.4 (5)
C2—C3—C7—C12	51.4 (4)	C17—C18—C19—C14	1.2 (5)
C4—C3—C7—C12	−79.0 (4)	C15—C14—C19—C18	−2.5 (5)
C2—C3—C7—C8	−134.0 (3)	C1—C14—C19—C18	178.3 (3)
C4—C3—C7—C8	95.7 (3)	O2—N3—C4—C5	167.1 (3)
C12—C7—C8—C9	2.9 (5)	O1—N3—C4—C5	−15.1 (4)
C3—C7—C8—C9	−172.2 (3)	O2—N3—C4—C6	47.3 (4)
C8—C7—C12—C11	−3.3 (5)	O1—N3—C4—C6	−134.9 (3)
C3—C7—C12—C11	171.4 (3)	O2—N3—C4—C3	−69.2 (3)
C3—C2—C1—N2	178.5 (3)	O1—N3—C4—C3	108.5 (3)
Se1—C2—C1—N2	0.2 (3)	C2—C3—C4—C5	−71.2 (3)
C3—C2—C1—C14	1.1 (5)	C7—C3—C4—C5	60.3 (3)
Se1—C2—C1—C14	−177.2 (3)	C2—C3—C4—C6	57.9 (4)
C19—C14—C1—C2	−42.9 (5)	C7—C3—C4—C6	−170.6 (3)
C15—C14—C1—C2	138.0 (3)	C2—C3—C4—N3	171.6 (2)
C19—C14—C1—N2	139.7 (3)	C7—C3—C4—N3	−56.9 (3)
C15—C14—C1—N2	−39.4 (4)	C8—C9—C10—C11	−2.5 (5)
C19—C14—C15—C16	1.7 (5)	C8—C9—C10—C13	175.5 (3)
C1—C14—C15—C16	−179.1 (3)	C7—C12—C11—C10	0.9 (6)
C16—C17—C18—C19	0.9 (5)	C9—C10—C11—C12	2.0 (5)
Cl1—C17—C18—C19	−179.4 (2)	C13—C10—C11—C12	−175.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.98	2.53	2.887 (4)	102
C5—H5A···Se1	0.96	2.71	3.387 (4)	128
C12—H12···Se1	0.93	2.85	3.546 (3)	132
C18—H18···O1ⁱ	0.93	2.46	3.393 (4)	177

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈ClN₃O₂Se
M_r	434.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	290
a, b, c (Å)	13.346 (3), 9.636 (2), 14.887 (3)
β (°)	95.668 (4)
V (Å³)	1905.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.35 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.527, 0.651
No. of measured, independent and observed [I > 2σ(I)] reflections	14877, 3884, 2618
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 1.01
No. of reflections	3884
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.23

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.98	2.53	2.887 (4)	101.6
C5—H5A···Se1	0.96	2.71	3.387 (4)	128.0
C12—H12···Se1	0.93	2.85	3.546 (3)	132.1
C18—H18···O1ⁱ	0.93	2.46	3.393 (4)	177

Symmetry code: (i) −x+1, −y+1, −z+1.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page