Diethyl 2-[(4-nitro­phen­yl)(4-phenyl-1,2,3-selenadiazol-5-yl)meth­yl]malonate

Marx, A.; Saravanan, S.; Muthusubramanian, S.; Manivannan, V.; Rath, N.P.

doi:10.1107/S160053680800706X

Diethyl 2-[(4-nitrophenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate

A. Marx, S. Saravanan, S. Muthusubramanian, V. Manivannan and N. P. Rath

In the title compound, C₂₂H₂₁N₃O₆Se, the heterocyclic ring makes dihedral angles of 50.03 (11) and 67.75 (11)°, respectively, with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions: the site occupancies for the C atoms are 0.62 (3)/0.38 (3) and 0.48 (3)/0.52 (3). In the crystal structure, weak intra- and intermolecular C-H

O interactions are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680800706X/is2278sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680800706X/is2278Isup2.hkl Contains datablock I

CCDC reference: 684528

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.054
wR factor = 0.162
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.86 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        Se1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  Se1    in Main Residue .          ?

Alert level G
PLAT793_ALERT_2_G Check the Absolute Configuration of C9     .....          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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 antibacterial (El-Kashef et al., 1986), antimicrobial (El-Bahaie et al., 1990) activities. The geometric parameters in the compound, (I) (Fig. 1), agree with the reported values of similar structures (Bertini et al., 1984; Gunasekaran et al., 2007).

The heterocyclic ring makes the dihedral angles of 50.03 (11) and 67.75 (11)° with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions; the site occupancies for the C atoms are 0.62/0.38 and 0.48/0.52. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing of (I) is stabilized by weak intermolecular C—H···O contacts (Table 1 and Fig. 2).

Related literature top

For biological activities, see: El-Kashef et al. (1986); El-Bahaie et al. (1990). For closely relaed compounds, see: Bertini et al. (1984); Gunasekaran et al. (2007).

Experimental top

2.22 g (0.02 mol) of powdered selenium dioxide was dissolved in glacial acetic acid by gentle warming. To this warm solution, 0.002 mol of diethyl 2-{3-[2-(aminocarbonyl)hydrazono]-1-(4-nitrophenyl)-3-phenylpropyl} malonate was added at once and the mixture was gently heated on a water bath until gas evolution ceased. The selenium deposited on cooling was removed by filtration and the filtrate poured into crushed ice, extracted with chloroform and purified by column chromatography, using silica gel (60–120 mesh) to yield diethyl 2-[(4-nitrophenyl) (4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate. Solvent used for crystallization is ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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

Diethyl 2-[(4-nitrophenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate top

Crystal data top

C₂₂H₂₁N₃O₆Se	Z = 2
M_r = 502.38	F(000) = 512
Triclinic, P1	D_x = 1.467 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9530 (6) Å	Cell parameters from 8446 reflections
b = 10.5220 (6) Å	θ = 1.7–26°
c = 12.2305 (7) Å	µ = 1.69 mm⁻¹
α = 79.350 (3)°	T = 295 K
β = 74.632 (3)°	Block, colourless
γ = 67.632 (3)°	0.23 × 0.17 × 0.16 mm
V = 1137.05 (11) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	4477 independent reflections
Radiation source: fine-focus sealed tube	3053 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 26.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.697, T_max = 0.773	k = −12→12
30194 measured reflections	l = −15→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0776P)² + 0.9842P] where P = (F_o² + 2F_c²)/3
4477 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.93 e Å⁻³
4 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₂₂H₂₁N₃O₆Se	γ = 67.632 (3)°
M_r = 502.38	V = 1137.05 (11) Å³
Triclinic, P1	Z = 2
a = 9.9530 (6) Å	Mo Kα radiation
b = 10.5220 (6) Å	µ = 1.69 mm⁻¹
c = 12.2305 (7) Å	T = 295 K
α = 79.350 (3)°	0.23 × 0.17 × 0.16 mm
β = 74.632 (3)°

Data collection top

Bruker SMART APEX area-detector diffractometer	4477 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3053 reflections with I > 2σ(I)
T_min = 0.697, T_max = 0.773	R_int = 0.028
30194 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.04	Δρ_max = 0.93 e Å⁻³
4477 reflections	Δρ_min = −0.80 e Å⁻³
313 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Se1	1.00900 (5)	0.21345 (6)	0.44996 (4)	0.0888 (3)
O1	1.5749 (5)	0.1019 (4)	−0.0847 (4)	0.1160 (15)
O2	1.6666 (5)	0.0959 (5)	0.0564 (5)	0.1327 (17)
O4	0.7916 (3)	0.6035 (4)	0.4808 (2)	0.0859 (10)
O6	1.0425 (4)	0.6499 (3)	0.1149 (2)	0.0859 (10)
N1	0.8397 (5)	0.1628 (5)	0.5006 (4)	0.0939 (13)
N2	0.7447 (4)	0.2286 (4)	0.4410 (3)	0.0753 (10)
N3	1.5628 (6)	0.1283 (4)	0.0109 (5)	0.0929 (14)
C1	0.7808 (4)	0.3215 (4)	0.3527 (3)	0.0558 (9)
C2	0.9155 (4)	0.3332 (4)	0.3410 (3)	0.0521 (8)
C3	0.6670 (4)	0.4007 (4)	0.2854 (3)	0.0542 (9)
C4	0.5213 (5)	0.4674 (5)	0.3410 (4)	0.0686 (11)
H4	0.4952	0.4563	0.4201	0.082*
C5	0.4156 (5)	0.5494 (5)	0.2804 (5)	0.0807 (13)
H5	0.3193	0.5953	0.3187	0.097*
C6	0.4514 (6)	0.5637 (5)	0.1641 (5)	0.0837 (14)
H6	0.3801	0.6198	0.1231	0.100*
C7	0.5930 (6)	0.4949 (5)	0.1085 (4)	0.0796 (13)
H7	0.6168	0.5031	0.0293	0.095*
C8	0.7013 (5)	0.4133 (5)	0.1679 (3)	0.0640 (10)
H8	0.7970	0.3671	0.1288	0.077*
C9	0.9818 (4)	0.4288 (4)	0.2556 (3)	0.0495 (8)
H9	0.9199	0.4661	0.1987	0.059*
C10	1.1371 (4)	0.3504 (4)	0.1923 (3)	0.0509 (8)
C11	1.1559 (5)	0.3109 (4)	0.0853 (3)	0.0627 (10)
H11	1.0739	0.3346	0.0529	0.075*
C12	1.2940 (5)	0.2375 (5)	0.0274 (4)	0.0738 (12)
H12	1.3063	0.2109	−0.0441	0.089*
C13	1.4136 (5)	0.2034 (4)	0.0754 (4)	0.0696 (12)
C14	1.4005 (5)	0.2414 (4)	0.1802 (4)	0.0677 (11)
H14	1.4837	0.2182	0.2110	0.081*
C15	1.2595 (4)	0.3154 (4)	0.2393 (3)	0.0592 (9)
H15	1.2477	0.3413	0.3109	0.071*
C16	0.9754 (4)	0.5531 (4)	0.3084 (3)	0.0529 (9)
H16	1.0474	0.5205	0.3577	0.064*
C17	0.8230 (4)	0.6224 (4)	0.3794 (3)	0.0574 (9)
O3	0.7304 (3)	0.7037 (3)	0.3154 (3)	0.0766 (8)
C18	0.5803 (5)	0.7789 (5)	0.3722 (6)	0.110 (2)
H18A	0.5602	0.7413	0.4510	0.132*	0.62 (3)
H18B	0.5088	0.7732	0.3345	0.132*	0.62 (3)
H18C	0.5834	0.7912	0.4481	0.132*	0.38 (3)
H18D	0.5213	0.7210	0.3811	0.132*	0.38 (3)
C19	0.571 (2)	0.9256 (10)	0.366 (2)	0.150 (8)	0.62 (3)
H19A	0.6297	0.9317	0.4139	0.226*	0.62 (3)
H19B	0.4690	0.9830	0.3907	0.226*	0.62 (3)
H19C	0.6074	0.9561	0.2886	0.226*	0.62 (3)
C19A	0.500 (3)	0.917 (2)	0.318 (2)	0.140 (12)	0.38 (3)
H19D	0.5704	0.9573	0.2711	0.209*	0.38 (3)
H19E	0.4360	0.9769	0.3760	0.209*	0.38 (3)
H19F	0.4407	0.9071	0.2717	0.209*	0.38 (3)
C20	1.0180 (4)	0.6576 (4)	0.2149 (3)	0.0580 (10)
O5	1.0258 (4)	0.7581 (3)	0.2602 (3)	0.0796 (9)
C21	1.0583 (9)	0.8667 (6)	0.1809 (6)	0.131 (3)
H21A	1.0011	0.8895	0.1224	0.157*	0.48 (3)
H21B	1.1629	0.8346	0.1442	0.157*	0.48 (3)
H21C	1.0677	0.8480	0.1040	0.157*	0.52 (3)
H21D	1.1521	0.8705	0.1864	0.157*	0.52 (3)
C22	1.022 (4)	0.9937 (15)	0.2377 (14)	0.109 (8)	0.48 (3)
H22A	0.9262	1.0138	0.2880	0.164*	0.48 (3)
H22B	1.0221	1.0702	0.1810	0.164*	0.48 (3)
H22C	1.0961	0.9786	0.2806	0.164*	0.48 (3)
C22A	0.937 (2)	1.0027 (12)	0.205 (2)	0.152 (8)	0.52 (3)
H22D	0.8533	1.0101	0.1765	0.228*	0.52 (3)
H22E	0.9727	1.0763	0.1694	0.228*	0.52 (3)
H22F	0.9072	1.0087	0.2862	0.228*	0.52 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0812 (4)	0.1012 (4)	0.0863 (4)	−0.0446 (3)	−0.0377 (3)	0.0424 (3)
O1	0.116 (3)	0.095 (3)	0.110 (3)	−0.042 (2)	0.047 (3)	−0.035 (2)
O2	0.067 (2)	0.126 (4)	0.170 (5)	−0.014 (2)	0.018 (3)	−0.035 (3)
O4	0.0721 (19)	0.109 (2)	0.0520 (17)	−0.0186 (18)	0.0079 (14)	−0.0072 (16)
O6	0.125 (3)	0.082 (2)	0.0519 (18)	−0.051 (2)	−0.0073 (17)	0.0087 (14)
N1	0.091 (3)	0.103 (3)	0.085 (3)	−0.051 (2)	−0.023 (2)	0.041 (2)
N2	0.070 (2)	0.082 (2)	0.070 (2)	−0.039 (2)	−0.0106 (18)	0.0203 (19)
N3	0.076 (3)	0.067 (3)	0.115 (4)	−0.029 (2)	0.025 (3)	−0.014 (3)
C1	0.059 (2)	0.060 (2)	0.049 (2)	−0.0287 (18)	−0.0026 (16)	−0.0018 (16)
C2	0.056 (2)	0.054 (2)	0.0456 (19)	−0.0232 (17)	−0.0087 (16)	0.0014 (15)
C3	0.054 (2)	0.058 (2)	0.055 (2)	−0.0286 (18)	−0.0118 (17)	0.0014 (17)
C4	0.061 (3)	0.082 (3)	0.066 (3)	−0.033 (2)	−0.004 (2)	−0.011 (2)
C5	0.055 (3)	0.082 (3)	0.109 (4)	−0.022 (2)	−0.021 (3)	−0.018 (3)
C6	0.080 (3)	0.076 (3)	0.108 (4)	−0.035 (3)	−0.047 (3)	0.015 (3)
C7	0.087 (3)	0.100 (3)	0.068 (3)	−0.052 (3)	−0.032 (2)	0.017 (2)
C8	0.060 (2)	0.080 (3)	0.059 (2)	−0.037 (2)	−0.0125 (19)	0.002 (2)
C9	0.0473 (19)	0.054 (2)	0.0480 (19)	−0.0215 (16)	−0.0091 (15)	0.0014 (15)
C10	0.052 (2)	0.0492 (19)	0.049 (2)	−0.0221 (17)	−0.0031 (16)	−0.0016 (15)
C11	0.065 (2)	0.071 (3)	0.053 (2)	−0.030 (2)	−0.0024 (19)	−0.0099 (19)
C12	0.083 (3)	0.077 (3)	0.061 (2)	−0.038 (3)	0.010 (2)	−0.018 (2)
C13	0.064 (3)	0.051 (2)	0.080 (3)	−0.025 (2)	0.020 (2)	−0.016 (2)
C14	0.053 (2)	0.057 (2)	0.087 (3)	−0.0197 (19)	−0.009 (2)	0.000 (2)
C15	0.054 (2)	0.057 (2)	0.061 (2)	−0.0173 (18)	−0.0054 (18)	−0.0079 (18)
C16	0.052 (2)	0.051 (2)	0.051 (2)	−0.0203 (17)	−0.0052 (16)	0.0026 (16)
C17	0.054 (2)	0.052 (2)	0.061 (2)	−0.0203 (18)	−0.0008 (18)	−0.0071 (18)
O3	0.0510 (16)	0.0754 (19)	0.0778 (19)	−0.0092 (14)	−0.0015 (14)	0.0076 (15)
C18	0.054 (3)	0.088 (4)	0.148 (5)	−0.004 (3)	0.004 (3)	0.003 (4)
C19	0.089 (11)	0.096 (9)	0.207 (18)	0.014 (7)	0.010 (11)	−0.036 (9)
C19A	0.083 (14)	0.159 (19)	0.119 (16)	−0.017 (14)	−0.001 (11)	0.041 (13)
C20	0.050 (2)	0.053 (2)	0.060 (2)	−0.0169 (17)	−0.0017 (17)	0.0025 (18)
O5	0.096 (2)	0.0653 (18)	0.0764 (19)	−0.0450 (17)	0.0138 (16)	−0.0137 (15)
C21	0.165 (6)	0.074 (4)	0.132 (5)	−0.070 (4)	0.049 (5)	−0.015 (3)
C22	0.134 (18)	0.069 (8)	0.116 (11)	−0.042 (9)	−0.006 (10)	0.000 (7)
C22A	0.168 (17)	0.117 (12)	0.181 (18)	−0.080 (13)	−0.056 (15)	0.053 (11)

Geometric parameters (Å, º) top

Se1—C2	1.836 (4)	C14—H14	0.9300
Se1—N1	1.875 (4)	C15—H15	0.9300
O1—N3	1.216 (6)	C16—C17	1.510 (5)
O2—N3	1.208 (7)	C16—C20	1.525 (5)
O4—C17	1.195 (5)	C16—H16	0.9800
O6—C20	1.195 (5)	C17—O3	1.315 (5)
N1—N2	1.260 (5)	O3—C18	1.447 (5)
N2—C1	1.386 (5)	C18—C19	1.4991 (10)
N3—C13	1.472 (6)	C18—C19A	1.4992 (10)
C1—C2	1.361 (5)	C18—H18A	0.9700
C1—C3	1.476 (5)	C18—H18B	0.9700
C2—C9	1.514 (5)	C18—H18C	0.9700
C3—C8	1.379 (5)	C18—H18D	0.9700
C3—C4	1.392 (5)	C19—H19A	0.9600
C4—C5	1.374 (6)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.366 (7)	C19A—H19D	0.9600
C5—H5	0.9300	C19A—H19E	0.9600
C6—C7	1.368 (7)	C19A—H19F	0.9600
C6—H6	0.9300	C20—O5	1.316 (5)
C7—C8	1.380 (6)	O5—C21	1.434 (6)
C7—H7	0.9300	C21—C22	1.4989 (10)
C8—H8	0.9300	C21—C22A	1.4990 (10)
C9—C10	1.517 (5)	C21—H21A	0.9700
C9—C16	1.535 (5)	C21—H21B	0.9700
C9—H9	0.9800	C21—H21C	0.9700
C10—C15	1.378 (5)	C21—H21D	0.9700
C10—C11	1.391 (5)	C22—H22A	0.9600
C11—C12	1.366 (6)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—C13	1.363 (7)	C22A—H22D	0.9600
C12—H12	0.9300	C22A—H22E	0.9600
C13—C14	1.371 (6)	C22A—H22F	0.9600
C14—C15	1.392 (5)

C2—Se1—N1	87.20 (17)	C17—C16—C9	111.8 (3)
N2—N1—Se1	110.9 (3)	C20—C16—C9	110.1 (3)
N1—N2—C1	117.2 (4)	C17—C16—H16	108.4
O2—N3—O1	123.6 (5)	C20—C16—H16	108.4
O2—N3—C13	117.9 (6)	C9—C16—H16	108.4
O1—N3—C13	118.5 (6)	O4—C17—O3	124.9 (4)
C2—C1—N2	115.9 (4)	O4—C17—C16	123.6 (4)
C2—C1—C3	127.3 (3)	O3—C17—C16	111.5 (3)
N2—C1—C3	116.7 (3)	C17—O3—C18	117.6 (4)
C1—C2—C9	127.6 (3)	O3—C18—C19	106.1 (6)
C1—C2—Se1	108.8 (3)	O3—C18—C19A	118.2 (9)
C9—C2—Se1	123.7 (3)	O3—C18—H18A	110.5
C8—C3—C4	118.5 (4)	C19—C18—H18A	110.5
C8—C3—C1	121.9 (3)	O3—C18—H18B	110.5
C4—C3—C1	119.6 (3)	C19—C18—H18B	110.5
C5—C4—C3	120.7 (4)	H18A—C18—H18B	108.7
C5—C4—H4	119.6	O3—C18—H18C	107.7
C3—C4—H4	119.6	C19A—C18—H18C	107.7
C6—C5—C4	120.2 (4)	O3—C18—H18D	107.7
C6—C5—H5	119.9	C19A—C18—H18D	107.7
C4—C5—H5	119.9	H18C—C18—H18D	107.1
C5—C6—C7	119.5 (5)	C18—C19—H19A	109.5
C5—C6—H6	120.3	C18—C19—H19B	109.5
C7—C6—H6	120.3	C18—C19—H19C	109.5
C6—C7—C8	121.1 (4)	C18—C19A—H19D	109.5
C6—C7—H7	119.4	C18—C19A—H19E	109.5
C8—C7—H7	119.4	H19D—C19A—H19E	109.5
C3—C8—C7	119.8 (4)	C18—C19A—H19F	109.5
C3—C8—H8	120.1	H19D—C19A—H19F	109.5
C7—C8—H8	120.1	H19E—C19A—H19F	109.5
C2—C9—C10	111.3 (3)	O6—C20—O5	124.2 (4)
C2—C9—C16	112.8 (3)	O6—C20—C16	125.6 (4)
C10—C9—C16	112.6 (3)	O5—C20—C16	110.2 (3)
C2—C9—H9	106.5	C20—O5—C21	115.6 (4)
C10—C9—H9	106.5	O5—C21—C22	112.0 (7)
C16—C9—H9	106.5	O5—C21—C22A	110.3 (8)
C15—C10—C11	119.3 (3)	O5—C21—H21A	109.2
C15—C10—C9	121.5 (3)	C22—C21—H21A	109.2
C11—C10—C9	119.1 (3)	O5—C21—H21B	109.2
C12—C11—C10	120.4 (4)	C22—C21—H21B	109.2
C12—C11—H11	119.8	H21A—C21—H21B	107.9
C10—C11—H11	119.8	O5—C21—H21C	109.6
C13—C12—C11	119.4 (4)	C22A—C21—H21C	109.6
C13—C12—H12	120.3	O5—C21—H21D	109.6
C11—C12—H12	120.3	C22A—C21—H21D	109.6
C12—C13—C14	122.2 (4)	H21C—C21—H21D	108.1
C12—C13—N3	119.1 (5)	C21—C22—H22A	109.5
C14—C13—N3	118.7 (5)	C21—C22—H22B	109.5
C13—C14—C15	118.3 (4)	C21—C22—H22C	109.5
C13—C14—H14	120.9	C21—C22A—H22D	109.5
C15—C14—H14	120.9	C21—C22A—H22E	109.5
C10—C15—C14	120.4 (4)	H22D—C22A—H22E	109.5
C10—C15—H15	119.8	C21—C22A—H22F	109.5
C14—C15—H15	119.8	H22D—C22A—H22F	109.5
C17—C16—C20	109.6 (3)	H22E—C22A—H22F	109.5

C2—Se1—N1—N2	0.3 (4)	C10—C11—C12—C13	−0.2 (6)
Se1—N1—N2—C1	0.3 (6)	C11—C12—C13—C14	−0.5 (6)
N1—N2—C1—C2	−1.0 (6)	C11—C12—C13—N3	−178.0 (4)
N1—N2—C1—C3	−178.4 (4)	O2—N3—C13—C12	−178.0 (5)
N2—C1—C2—C9	−177.9 (4)	O1—N3—C13—C12	1.8 (6)
C3—C1—C2—C9	−0.8 (6)	O2—N3—C13—C14	4.4 (6)
N2—C1—C2—Se1	1.1 (4)	O1—N3—C13—C14	−175.8 (4)
C3—C1—C2—Se1	178.2 (3)	C12—C13—C14—C15	0.9 (6)
N1—Se1—C2—C1	−0.8 (3)	N3—C13—C14—C15	178.4 (4)
N1—Se1—C2—C9	178.3 (3)	C11—C10—C15—C14	0.1 (5)
C2—C1—C3—C8	50.7 (6)	C9—C10—C15—C14	178.9 (3)
N2—C1—C3—C8	−132.2 (4)	C13—C14—C15—C10	−0.7 (6)
C2—C1—C3—C4	−127.9 (4)	C2—C9—C16—C17	−48.0 (4)
N2—C1—C3—C4	49.2 (5)	C10—C9—C16—C17	−175.1 (3)
C8—C3—C4—C5	−3.1 (6)	C2—C9—C16—C20	−170.0 (3)
C1—C3—C4—C5	175.6 (4)	C10—C9—C16—C20	62.9 (4)
C3—C4—C5—C6	1.7 (7)	C20—C16—C17—O4	−138.2 (4)
C4—C5—C6—C7	0.5 (7)	C9—C16—C17—O4	99.5 (5)
C5—C6—C7—C8	−1.3 (7)	C20—C16—C17—O3	42.6 (4)
C4—C3—C8—C7	2.3 (6)	C9—C16—C17—O3	−79.7 (4)
C1—C3—C8—C7	−176.4 (4)	O4—C17—O3—C18	1.7 (6)
C6—C7—C8—C3	−0.1 (7)	C16—C17—O3—C18	−179.0 (4)
C1—C2—C9—C10	−128.4 (4)	C17—O3—C18—C19	105.5 (15)
Se1—C2—C9—C10	52.8 (4)	C17—O3—C18—C19A	149 (2)
C1—C2—C9—C16	103.8 (4)	C17—C16—C20—O6	−118.3 (4)
Se1—C2—C9—C16	−75.0 (4)	C9—C16—C20—O6	5.1 (6)
C2—C9—C10—C15	−81.3 (4)	C17—C16—C20—O5	62.4 (4)
C16—C9—C10—C15	46.6 (4)	C9—C16—C20—O5	−174.3 (3)
C2—C9—C10—C11	97.5 (4)	O6—C20—O5—C21	3.5 (7)
C16—C9—C10—C11	−134.6 (3)	C16—C20—O5—C21	−177.2 (5)
C15—C10—C11—C12	0.3 (6)	C20—O5—C21—C22	163.5 (15)
C9—C10—C11—C12	−178.5 (4)	C20—O5—C21—C22A	121.8 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22A—H22D···O2ⁱ	0.96	2.47	3.38 (4)	159
C11—H11···O6ⁱⁱ	0.93	2.56	3.410 (6)	152
C18—H18A···O4	0.97	2.29	2.686 (7)	103
C21—H21C···O6	0.97	2.17	2.627 (6)	107

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁N₃O₆Se
M_r	502.38
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.9530 (6), 10.5220 (6), 12.2305 (7)
α, β, γ (°)	79.350 (3), 74.632 (3), 67.632 (3)
V (Å³)	1137.05 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.69
Crystal size (mm)	0.23 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.697, 0.773
No. of measured, independent and observed [I > 2σ(I)] reflections	30194, 4477, 3053
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.161, 1.04
No. of reflections	4477
No. of parameters	313
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.93, −0.80

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).