Bis(2-nitro­phen­yl) selenide, bis­(2-amino­phen­yl) selenide and bis­(2-amino­phen­yl) telluride: structural and theoretical analysis

Saravanan, R.; Singh, H.B.; Butcher, R.J.

doi:10.1107/S2053229621005015

Bis(2-nitrophenyl) selenide, bis(2-aminophenyl) selenide and bis(2-aminophenyl) telluride: structural and theoretical analysis

R. Saravanan, H. B. Singh and R. J. Butcher

Three organoselenium and organotellurium compounds containing ortho substitutents, namely, bis(2-nitrophenyl) selenide, C₁₂H₈N₂O₄Se, 2, bis(2-aminophenyl) selenide, C₁₂H₁₂N₂Se, 3, and bis(2-aminophenyl) telluride, C₁₂H₁₂N₂Te, 7, have been investigated by both structural and theoretical methods. In the structures of all three compounds, there are intramolecular contacts between both Se and Te with the ortho substituents. In the case of 2, this is achieved by rotation of the nitro group from the arene plane. For 3, both amino groups exhibit pyramidal geometry and are involved in intramolecular N—H

Se interactions, with one also participating in intermolecular N—H

N hydrogen bonding. While 3 and 7 are structurally similar, there are some significant differences. In addition to both intramolecular N—H

Te interactions and intermolecular N—H

N hydrogen bonding, 7 also exhibits intramolecular N—H

N hydrogen bonding. In the packing of these molecules, for 2, there are weak intermolecular C—H

O contacts and these, along with the O

N interactions mentioned above, link the molecules into a three-dimensional array. For 3, in addition to the N—H

N and N—H

Se interactions, there are also weak intermolecular C—H

Se interactions, which also link the molecules into a three-dimensional array. On the other hand, 7 shows intermolecular N—H

N interactions linking the molecules into R₂²(16) centrosymmetric dimers. In the theoretical studies, for compound 2, AIM (atoms in molecules) analysis revealed critical points in the Se

O interactions with values of 0.017 and 0.026 a.u. These values are suggestive of weak interactions present between Se and O atoms. For 3 and 7, the molecular structures displayed intramolecular, as well as intermolecular, hydrogen-bond interactions of the N—H

N type. The strength of this hydrogen-bond interaction was calculated by AIM analysis. Here, the intermolecular (N—H

N) hydrogen bond is stronger than the intramolecular hydrogen bond. This was confirmed by the electron densities for 3 and 7 [ρ_(r) = 0.015 and 0.011, respectively].

Keywords: selenide; telluride; crystal structure; organotellurium; organoselenium; AIM analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621005015/zo3004sup1.cif Contains datablocks 2, 3, 7, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621005015/zo30042sup2.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621005015/zo30043sup3.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621005015/zo30047sup4.hkl Contains datablock 7
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621005015/zo3004sup5.pdf NMR and MS spectra

CCDC references: 2083079; 2083078; 2083077

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015\); cell refinement: CrysAlis PRO (Rigaku OD, 2015\); data reduction: CrysAlis PRO (Rigaku OD, 2015\); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a\); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b\); molecular graphics: SHELXTL (Sheldrick, 2008\); software used to prepare material for publication: SHELXTL (Sheldrick, 2008\).

Bis(2-nitrophenyl) selenide (2) top

Crystal data top

C₁₂H₈N₂O₄Se	Z = 2
M_r = 323.16	F(000) = 320
Triclinic, P1	D_x = 1.825 Mg m⁻³
a = 7.6530 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8066 (5) Å	Cell parameters from 5131 reflections
c = 11.5939 (5) Å	θ = 3.1–31.1°
α = 76.603 (5)°	µ = 3.21 mm⁻¹
β = 88.358 (5)°	T = 100 K
γ = 61.263 (8)°	Block, clear intense yellow
V = 588.04 (8) Å³	0.24 × 0.20 × 0.13 mm

Data collection top

Rigaku Saturn 724 Dual Source CCD diffractometer	2886 independent reflections
Radiation source: fine-focus sealed X-ray tube	2743 reflections with I > 2σ(I)
Detector resolution: 7.111 pixels mm^-1	R_int = 0.041
ω scans	θ_max = 28.3°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015\)	h = −10→10
T_min = 0.595, T_max = 1.000	k = −10→10
5993 measured reflections	l = −14→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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F²) = 0.080	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0429P)² + 0.6023P] where P = (F_o² + 2F_c²)/3
2886 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Se1	0.66633 (3)	0.56956 (3)	0.21267 (2)	0.01707 (9)
O1	1.1527 (3)	0.0686 (3)	0.46381 (18)	0.0274 (4)
O2	0.9363 (3)	0.1902 (3)	0.31035 (16)	0.0298 (4)
O3	0.3013 (3)	0.6932 (3)	0.06118 (16)	0.0234 (4)
O4	0.0310 (3)	0.8944 (3)	0.12896 (15)	0.0244 (4)
N1	0.9922 (3)	0.1974 (3)	0.40594 (18)	0.0194 (4)
N2	0.2043 (3)	0.8386 (3)	0.10331 (16)	0.0180 (4)
C1	0.8590 (3)	0.3677 (3)	0.4545 (2)	0.0153 (4)
C2	0.8910 (3)	0.3447 (4)	0.5757 (2)	0.0183 (4)
H2	0.991 (5)	0.228 (5)	0.619 (3)	0.032 (8)*
C3	0.7654 (4)	0.5001 (4)	0.6261 (2)	0.0196 (4)
H3	0.784 (4)	0.482 (5)	0.702 (3)	0.021 (7)*
C4	0.6098 (4)	0.6745 (4)	0.5548 (2)	0.0188 (4)
H4	0.519 (5)	0.775 (5)	0.585 (3)	0.028 (8)*
C5	0.5795 (3)	0.6959 (3)	0.43393 (19)	0.0153 (4)
H5	0.474 (5)	0.814 (5)	0.384 (3)	0.020 (7)*
C6	0.7060 (3)	0.5420 (3)	0.38004 (18)	0.0133 (4)
C7	0.5000 (3)	0.8590 (3)	0.16682 (18)	0.0143 (4)
C8	0.5794 (3)	0.9816 (4)	0.1792 (2)	0.0178 (4)
H8	0.715 (5)	0.925 (4)	0.211 (3)	0.018 (7)*
C9	0.4628 (4)	1.1896 (4)	0.1500 (2)	0.0199 (4)
H9	0.528 (5)	1.268 (5)	0.154 (3)	0.027 (8)*
C10	0.2614 (4)	1.2812 (4)	0.1079 (2)	0.0195 (4)
H10	0.181 (5)	1.419 (5)	0.089 (3)	0.020 (7)*
C11	0.1778 (4)	1.1630 (4)	0.09536 (19)	0.0192 (4)
H11	0.048 (5)	1.221 (5)	0.065 (3)	0.025 (8)*
C12	0.2984 (3)	0.9560 (3)	0.12272 (18)	0.0154 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.02034 (14)	0.01286 (13)	0.01461 (12)	−0.00518 (9)	0.00327 (8)	−0.00431 (8)
O1	0.0151 (8)	0.0152 (8)	0.0413 (10)	−0.0017 (7)	0.0046 (7)	−0.0015 (7)
O2	0.0398 (11)	0.0160 (8)	0.0216 (8)	−0.0039 (8)	0.0078 (7)	−0.0062 (7)
O3	0.0292 (9)	0.0180 (8)	0.0251 (8)	−0.0125 (7)	−0.0007 (7)	−0.0065 (7)
O4	0.0210 (8)	0.0320 (10)	0.0231 (8)	−0.0169 (8)	0.0014 (6)	−0.0026 (7)
N1	0.0171 (9)	0.0108 (9)	0.0259 (10)	−0.0045 (7)	0.0093 (7)	−0.0027 (7)
N2	0.0226 (9)	0.0193 (9)	0.0139 (8)	−0.0134 (8)	−0.0006 (7)	0.0002 (7)
C1	0.0122 (9)	0.0124 (10)	0.0214 (10)	−0.0055 (8)	0.0070 (8)	−0.0057 (8)
C2	0.0160 (10)	0.0154 (10)	0.0218 (10)	−0.0082 (9)	0.0000 (8)	−0.0001 (9)
C3	0.0230 (11)	0.0204 (11)	0.0161 (10)	−0.0113 (9)	0.0015 (8)	−0.0040 (9)
C4	0.0207 (11)	0.0167 (11)	0.0186 (10)	−0.0083 (9)	0.0073 (8)	−0.0066 (9)
C5	0.0129 (9)	0.0133 (10)	0.0170 (10)	−0.0045 (8)	0.0041 (7)	−0.0035 (8)
C6	0.0117 (9)	0.0150 (10)	0.0147 (9)	−0.0074 (8)	0.0047 (7)	−0.0050 (8)
C7	0.0167 (10)	0.0122 (9)	0.0137 (9)	−0.0073 (8)	0.0035 (7)	−0.0025 (7)
C8	0.0180 (10)	0.0201 (11)	0.0169 (9)	−0.0110 (9)	0.0023 (8)	−0.0038 (8)
C9	0.0288 (12)	0.0202 (11)	0.0174 (10)	−0.0166 (10)	0.0057 (9)	−0.0062 (9)
C10	0.0275 (12)	0.0133 (10)	0.0164 (10)	−0.0088 (9)	0.0025 (8)	−0.0042 (8)
C11	0.0200 (11)	0.0194 (11)	0.0146 (9)	−0.0069 (9)	0.0004 (8)	−0.0041 (8)
C12	0.0199 (10)	0.0163 (10)	0.0127 (9)	−0.0112 (9)	0.0023 (7)	−0.0031 (8)

Geometric parameters (Å, º) top

Se1—C6	1.919 (2)	C3—H3	0.86 (3)
Se1—C7	1.930 (2)	C4—C5	1.385 (3)
Se1—O2	2.6490 (19)	C4—H4	0.90 (3)
Se1—O3	2.9534 (18)	C5—C6	1.402 (3)
O1—N1	1.232 (3)	C5—H5	0.95 (3)
O2—N1	1.222 (3)	C7—C8	1.390 (3)
O3—N2	1.227 (3)	C7—C12	1.399 (3)
O4—N2	1.232 (3)	C8—C9	1.385 (3)
N1—C1	1.461 (3)	C8—H8	0.95 (3)
N2—C12	1.466 (3)	C9—C10	1.395 (3)
C1—C2	1.388 (3)	C9—H9	0.97 (3)
C1—C6	1.396 (3)	C10—C11	1.385 (3)
C2—C3	1.383 (3)	C10—H10	0.92 (3)
C2—H2	0.90 (4)	C11—C12	1.382 (3)
C3—C4	1.390 (3)	C11—H11	0.91 (3)

C6—Se1—C7	97.38 (9)	C3—C4—H4	122 (2)
C6—Se1—O2	72.21 (7)	C4—C5—C6	120.8 (2)
C7—Se1—O2	167.00 (8)	C4—C5—H5	122.3 (18)
C6—Se1—O3	130.54 (7)	C6—C5—H5	116.9 (18)
C7—Se1—O3	68.23 (7)	C1—C6—C5	116.68 (19)
O2—Se1—O3	124.39 (6)	C1—C6—Se1	122.05 (15)
N1—O2—Se1	103.45 (13)	C5—C6—Se1	121.27 (16)
N2—O3—Se1	91.39 (12)	C8—C7—C12	116.8 (2)
O2—N1—O1	123.8 (2)	C8—C7—Se1	119.70 (17)
O2—N1—C1	117.76 (19)	C12—C7—Se1	123.47 (16)
O1—N1—C1	118.5 (2)	C9—C8—C7	121.2 (2)
O3—N2—O4	124.1 (2)	C9—C8—H8	117.6 (17)
O3—N2—C12	118.21 (19)	C7—C8—H8	121.2 (17)
O4—N2—C12	117.69 (19)	C8—C9—C10	120.5 (2)
C2—C1—C6	123.04 (19)	C8—C9—H9	118 (2)
C2—C1—N1	117.0 (2)	C10—C9—H9	122 (2)
C6—C1—N1	119.98 (19)	C11—C10—C9	119.7 (2)
C3—C2—C1	119.0 (2)	C11—C10—H10	118.7 (19)
C3—C2—H2	122 (2)	C9—C10—H10	121.6 (19)
C1—C2—H2	119 (2)	C12—C11—C10	118.7 (2)
C2—C3—C4	119.4 (2)	C12—C11—H11	121 (2)
C2—C3—H3	118 (2)	C10—C11—H11	121 (2)
C4—C3—H3	123 (2)	C11—C12—C7	123.1 (2)
C5—C4—C3	121.1 (2)	C11—C12—N2	116.4 (2)
C5—C4—H4	117 (2)	C7—C12—N2	120.4 (2)

Se1—O2—N1—O1	−158.92 (19)	C4—C5—C6—C1	1.1 (3)
Se1—O2—N1—C1	21.9 (2)	C4—C5—C6—Se1	−179.89 (17)
Se1—O3—N2—O4	−139.31 (19)	C12—C7—C8—C9	0.6 (3)
Se1—O3—N2—C12	41.74 (18)	Se1—C7—C8—C9	−178.33 (17)
O2—N1—C1—C2	160.4 (2)	C7—C8—C9—C10	0.4 (3)
O1—N1—C1—C2	−18.8 (3)	C8—C9—C10—C11	0.0 (3)
O2—N1—C1—C6	−18.6 (3)	C9—C10—C11—C12	−1.4 (3)
O1—N1—C1—C6	162.2 (2)	C10—C11—C12—C7	2.4 (3)
C6—C1—C2—C3	0.5 (3)	C10—C11—C12—N2	−177.64 (19)
N1—C1—C2—C3	−178.4 (2)	C8—C7—C12—C11	−2.0 (3)
C1—C2—C3—C4	0.4 (3)	Se1—C7—C12—C11	176.85 (17)
C2—C3—C4—C5	−0.5 (4)	C8—C7—C12—N2	178.06 (19)
C3—C4—C5—C6	−0.3 (4)	Se1—C7—C12—N2	−3.1 (3)
C2—C1—C6—C5	−1.3 (3)	O3—N2—C12—C11	139.8 (2)
N1—C1—C6—C5	177.61 (19)	O4—N2—C12—C11	−39.2 (3)
C2—C1—C6—Se1	179.76 (17)	O3—N2—C12—C7	−40.3 (3)
N1—C1—C6—Se1	−1.4 (3)	O4—N2—C12—C7	140.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95 (3)	2.62 (3)	3.243 (3)	123 (2)
C8—H8···O4ⁱⁱ	0.95 (3)	2.50 (3)	3.249 (3)	136 (2)

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

Bis(2-aminophenyl) selenide (3) top

Crystal data top

C₁₂H₁₂N₂Se	F(000) = 528
M_r = 263.20	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4557 (2) Å	Cell parameters from 9148 reflections
b = 7.0530 (2) Å	θ = 2.7–31.2°
c = 18.0521 (5) Å	µ = 3.46 mm⁻¹
β = 92.643 (3)°	T = 100 K
V = 1075.45 (5) Å³	Prism, colorless
Z = 4	0.30 × 0.28 × 0.17 mm

Data collection top

Rigaku Saturn 724 Dual Source CCD diffractometer	2695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.073
ω scans	θ_max = 31.2°, θ_min = 2.3°
Absorption correction: numerical (NUMABS; Rigaku, 1999\)	h = −11→11
T_min = 0.382, T_max = 0.557	k = −9→9
14393 measured reflections	l = −26→26
3168 independent reflections

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)] = 0.048	Hydrogen site location: mixed
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0718P)² + 1.7514P] where P = (F_o² + 2F_c²)/3
3168 reflections	(Δ/σ)_max = 0.001
152 parameters	Δρ_max = 1.58 e Å⁻³
4 restraints	Δρ_min = −0.83 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Se1	0.51147 (3)	0.81805 (4)	0.71295 (2)	0.02687 (13)
N1	0.4090 (4)	0.8113 (4)	0.54406 (18)	0.0342 (6)
H1A	0.382 (11)	0.807 (12)	0.4971 (16)	0.12 (3)*
H1B	0.478 (5)	0.885 (6)	0.565 (2)	0.047 (13)*
N2	0.6668 (4)	1.1596 (4)	0.62818 (18)	0.0342 (6)
H2A	0.726 (9)	1.258 (8)	0.626 (5)	0.12 (3)*
H2B	0.593 (4)	1.169 (6)	0.659 (2)	0.037 (12)*
C1	0.4153 (3)	0.6178 (5)	0.65435 (17)	0.0256 (6)
C2	0.3744 (4)	0.4510 (5)	0.6904 (2)	0.0335 (7)
H2	0.397311	0.437362	0.742090	0.040*
C3	0.3005 (4)	0.3056 (5)	0.6508 (3)	0.0394 (9)
H3	0.269982	0.193213	0.675358	0.047*
C4	0.2714 (4)	0.3248 (5)	0.5752 (3)	0.0398 (9)
H4	0.223860	0.223470	0.547598	0.048*
C5	0.3113 (4)	0.4917 (5)	0.5393 (2)	0.0336 (7)
H5	0.290883	0.502654	0.487335	0.040*
C6	0.3809 (3)	0.6431 (5)	0.57857 (18)	0.0275 (6)
C7	0.7113 (3)	0.8318 (4)	0.66588 (17)	0.0236 (6)
C8	0.8086 (4)	0.6711 (5)	0.6664 (2)	0.0298 (6)
H8	0.774217	0.557629	0.689027	0.036*
C9	0.9543 (4)	0.6755 (5)	0.6343 (2)	0.0352 (7)
H9	1.019774	0.566000	0.634625	0.042*
C10	1.0027 (4)	0.8417 (6)	0.6019 (2)	0.0363 (8)
H10	1.102199	0.845802	0.579549	0.044*
C11	0.9090 (4)	1.0023 (5)	0.60149 (18)	0.0318 (7)
H11	0.944985	1.115175	0.579032	0.038*
C12	0.7605 (4)	1.0003 (5)	0.63404 (16)	0.0261 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.02233 (18)	0.03051 (19)	0.02851 (18)	0.00105 (11)	0.00909 (11)	0.00240 (11)
N1	0.0369 (16)	0.0339 (15)	0.0319 (14)	−0.0017 (12)	0.0028 (12)	0.0053 (12)
N2	0.0331 (15)	0.0315 (15)	0.0387 (15)	0.0069 (12)	0.0082 (12)	0.0026 (12)
C1	0.0178 (12)	0.0259 (13)	0.0336 (14)	0.0019 (10)	0.0077 (10)	0.0042 (12)
C2	0.0251 (14)	0.0286 (15)	0.0478 (18)	0.0055 (12)	0.0135 (13)	0.0097 (14)
C3	0.0322 (17)	0.0245 (15)	0.063 (2)	0.0011 (12)	0.0204 (16)	0.0086 (15)
C4	0.0221 (15)	0.0273 (16)	0.071 (3)	−0.0032 (11)	0.0129 (15)	−0.0099 (16)
C5	0.0245 (14)	0.0335 (16)	0.0432 (18)	0.0019 (12)	0.0067 (13)	−0.0040 (14)
C6	0.0187 (12)	0.0290 (14)	0.0356 (15)	0.0007 (10)	0.0079 (11)	0.0023 (12)
C7	0.0173 (12)	0.0272 (14)	0.0268 (13)	0.0013 (10)	0.0064 (10)	−0.0001 (11)
C8	0.0246 (14)	0.0301 (16)	0.0346 (16)	0.0051 (11)	0.0018 (12)	−0.0026 (13)
C9	0.0261 (15)	0.0412 (19)	0.0386 (18)	0.0095 (13)	0.0054 (13)	−0.0024 (14)
C10	0.0235 (15)	0.051 (2)	0.0345 (16)	0.0060 (13)	0.0075 (12)	−0.0020 (15)
C11	0.0269 (14)	0.0383 (17)	0.0307 (15)	−0.0054 (12)	0.0057 (11)	0.0029 (13)
C12	0.0250 (13)	0.0310 (15)	0.0225 (12)	−0.0012 (11)	0.0039 (10)	0.0001 (11)

Geometric parameters (Å, º) top

Se1—C1	1.922 (3)	C4—C5	1.393 (5)
Se1—C7	1.928 (3)	C4—H4	0.9500
N1—C6	1.366 (4)	C5—C6	1.397 (5)
N1—H1A	0.87 (2)	C5—H5	0.9500
N1—H1B	0.856 (19)	C7—C12	1.392 (4)
N2—C12	1.376 (4)	C7—C8	1.400 (4)
N2—H2A	0.85 (2)	C8—C9	1.386 (5)
N2—H2B	0.861 (19)	C8—H8	0.9500
C1—C2	1.395 (4)	C9—C10	1.381 (5)
C1—C6	1.397 (4)	C9—H9	0.9500
C2—C3	1.383 (6)	C10—C11	1.382 (5)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.381 (7)	C11—C12	1.411 (4)
C3—H3	0.9500	C11—H11	0.9500

C1—Se1—C7	98.72 (12)	N1—C6—C5	120.7 (3)
C6—N1—H1A	112 (6)	N1—C6—C1	121.7 (3)
C6—N1—H1B	117 (3)	C5—C6—C1	117.6 (3)
H1A—N1—H1B	126 (7)	C12—C7—C8	120.5 (3)
C12—N2—H2A	109 (6)	C12—C7—Se1	120.6 (2)
C12—N2—H2B	116 (3)	C8—C7—Se1	118.9 (2)
H2A—N2—H2B	114 (7)	C9—C8—C7	120.8 (3)
C2—C1—C6	121.3 (3)	C9—C8—H8	119.6
C2—C1—Se1	118.1 (2)	C7—C8—H8	119.6
C6—C1—Se1	120.6 (2)	C10—C9—C8	118.9 (3)
C3—C2—C1	120.0 (3)	C10—C9—H9	120.6
C3—C2—H2	120.0	C8—C9—H9	120.6
C1—C2—H2	120.0	C9—C10—C11	121.1 (3)
C4—C3—C2	119.6 (3)	C9—C10—H10	119.4
C4—C3—H3	120.2	C11—C10—H10	119.4
C2—C3—H3	120.2	C10—C11—C12	120.7 (3)
C3—C4—C5	120.4 (3)	C10—C11—H11	119.6
C3—C4—H4	119.8	C12—C11—H11	119.6
C5—C4—H4	119.8	N2—C12—C7	123.2 (3)
C4—C5—C6	121.1 (4)	N2—C12—C11	118.7 (3)
C4—C5—H5	119.5	C7—C12—C11	118.0 (3)
C6—C5—H5	119.5

C6—C1—C2—C3	1.0 (4)	C12—C7—C8—C9	−1.0 (5)
Se1—C1—C2—C3	178.0 (2)	Se1—C7—C8—C9	−178.9 (3)
C1—C2—C3—C4	1.7 (5)	C7—C8—C9—C10	0.2 (5)
C2—C3—C4—C5	−2.1 (5)	C8—C9—C10—C11	0.4 (6)
C3—C4—C5—C6	−0.2 (5)	C9—C10—C11—C12	−0.2 (5)
C4—C5—C6—N1	−175.1 (3)	C8—C7—C12—N2	176.3 (3)
C4—C5—C6—C1	2.8 (4)	Se1—C7—C12—N2	−5.8 (4)
C2—C1—C6—N1	174.7 (3)	C8—C7—C12—C11	1.1 (5)
Se1—C1—C6—N1	−2.3 (4)	Se1—C7—C12—C11	179.0 (2)
C2—C1—C6—C5	−3.2 (4)	C10—C11—C12—N2	−175.9 (3)
Se1—C1—C6—C5	179.9 (2)	C10—C11—C12—C7	−0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.87 (2)	2.29 (2)	3.152 (5)	171 (8)
N1—H1B···Se1	0.86 (2)	2.72 (5)	3.131 (3)	111 (4)
N2—H2B···Se1	0.86 (2)	2.76 (4)	3.171 (3)	111 (3)
C8—H8···Se1ⁱⁱ	0.95	3.00	3.599 (3)	123

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3/2, y−1/2, −z+3/2.

Bis(2-aminophenyl) telluride (7) top

Crystal data top

C₁₂H₁₂N₂Te	Z = 2
M_r = 311.84	F(000) = 300
Triclinic, P1	D_x = 1.853 Mg m⁻³
a = 7.0048 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6062 (3) Å	Cell parameters from 6288 reflections
c = 10.1392 (3) Å	θ = 2.2–30.9°
α = 66.164 (3)°	µ = 2.63 mm⁻¹
β = 88.628 (2)°	T = 150 K
γ = 88.780 (2)°	Prism, pale yellow
V = 558.90 (3) Å³	0.21 × 0.16 × 0.12 mm

Data collection top

Rigaku Saturn 724 Dual Source CCD diffractometer	2890 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.038
ω scans	θ_max = 29.1°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015\)	h = −9→9
T_min = 0.567, T_max = 0.714	k = −11→11
13367 measured reflections	l = −13→13
2976 independent reflections

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)] = 0.020	Hydrogen site location: mixed
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0215P)² + 0.5277P] where P = (F_o² + 2F_c²)/3
2976 reflections	(Δ/σ)_max = 0.001
152 parameters	Δρ_max = 1.27 e Å⁻³
4 restraints	Δρ_min = −1.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Te1	0.79904 (2)	0.71267 (2)	0.05875 (2)	0.02352 (5)
N1	1.1524 (3)	0.4620 (3)	0.2470 (2)	0.0332 (4)
H1N1	1.151 (5)	0.570 (2)	0.185 (3)	0.044 (8)*
H1N2	1.260 (4)	0.408 (4)	0.254 (4)	0.066 (11)*
N2	0.8161 (3)	0.6373 (3)	0.4087 (2)	0.0288 (4)
H2N1	0.893 (4)	0.598 (4)	0.364 (3)	0.032 (7)*
H2N2	0.821 (4)	0.588 (4)	0.5008 (19)	0.041 (8)*
C1	0.8319 (3)	0.4444 (2)	0.1672 (2)	0.0230 (4)
C2	1.0018 (3)	0.3687 (3)	0.2356 (2)	0.0244 (4)
C3	1.0123 (3)	0.1897 (3)	0.3027 (2)	0.0306 (4)
H3	1.126508	0.136094	0.349196	0.037*
C4	0.8600 (4)	0.0911 (3)	0.3021 (2)	0.0342 (5)
H4	0.870739	−0.029119	0.348067	0.041*
C5	0.6920 (4)	0.1654 (3)	0.2352 (3)	0.0341 (5)
H5	0.586994	0.097238	0.235456	0.041*
C6	0.6791 (3)	0.3409 (3)	0.1679 (2)	0.0295 (4)
H6	0.564225	0.392455	0.121032	0.035*
C7	0.5972 (3)	0.7416 (2)	0.2063 (2)	0.0210 (3)
C8	0.6391 (3)	0.6977 (2)	0.3521 (2)	0.0228 (4)
C9	0.4957 (3)	0.7238 (3)	0.4406 (2)	0.0282 (4)
H9	0.519978	0.692485	0.539947	0.034*
C10	0.3199 (3)	0.7938 (3)	0.3865 (2)	0.0296 (4)
H10	0.225347	0.809897	0.448766	0.035*
C11	0.2809 (3)	0.8409 (3)	0.2414 (3)	0.0287 (4)
H11	0.161479	0.891668	0.203528	0.034*
C12	0.4188 (3)	0.8127 (2)	0.1531 (2)	0.0250 (4)
H12	0.391751	0.842237	0.054446	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Te1	0.02854 (8)	0.01968 (7)	0.02071 (8)	0.00115 (5)	0.00508 (5)	−0.00683 (5)
N1	0.0311 (9)	0.0326 (10)	0.0356 (10)	−0.0015 (8)	−0.0011 (8)	−0.0132 (8)
N2	0.0280 (9)	0.0359 (9)	0.0217 (8)	0.0065 (7)	−0.0018 (7)	−0.0110 (7)
C1	0.0278 (9)	0.0207 (8)	0.0207 (9)	0.0016 (7)	0.0052 (7)	−0.0090 (7)
C2	0.0297 (9)	0.0257 (9)	0.0196 (9)	0.0033 (7)	0.0036 (7)	−0.0113 (7)
C3	0.0385 (11)	0.0296 (10)	0.0242 (10)	0.0098 (8)	0.0013 (8)	−0.0119 (8)
C4	0.0520 (14)	0.0222 (9)	0.0279 (11)	−0.0013 (9)	0.0088 (9)	−0.0102 (8)
C5	0.0419 (12)	0.0278 (10)	0.0340 (11)	−0.0075 (9)	0.0096 (9)	−0.0142 (9)
C6	0.0301 (10)	0.0283 (10)	0.0315 (11)	−0.0012 (8)	0.0051 (8)	−0.0137 (9)
C7	0.0237 (8)	0.0170 (8)	0.0229 (9)	0.0000 (6)	0.0036 (7)	−0.0088 (7)
C8	0.0269 (9)	0.0181 (8)	0.0230 (9)	0.0002 (7)	0.0020 (7)	−0.0080 (7)
C9	0.0334 (10)	0.0274 (10)	0.0230 (9)	0.0009 (8)	0.0053 (8)	−0.0096 (8)
C10	0.0288 (10)	0.0271 (10)	0.0343 (11)	0.0002 (8)	0.0088 (8)	−0.0144 (9)
C11	0.0231 (9)	0.0257 (9)	0.0382 (11)	0.0021 (7)	0.0012 (8)	−0.0139 (9)
C12	0.0270 (9)	0.0227 (9)	0.0265 (10)	0.0008 (7)	−0.0008 (7)	−0.0110 (8)

Geometric parameters (Å, º) top

Te1—C7	2.1180 (18)	C4—C5	1.382 (4)
Te1—C1	2.1286 (19)	C4—H4	0.9500
Te1—H1N1	2.83 (3)	C5—C6	1.385 (3)
Te1—H2N1	2.93 (3)	C5—H5	0.9500
N1—C2	1.373 (3)	C6—H6	0.9500
N1—N2	3.490 (3)	C7—C12	1.400 (3)
N1—H1N1	0.883 (18)	C7—C8	1.406 (3)
N1—H1N2	0.868 (18)	C8—C9	1.406 (3)
N2—C8	1.379 (3)	C9—C10	1.384 (3)
N2—H2N1	0.848 (17)	C9—H9	0.9500
N2—H2N2	0.857 (17)	C10—C11	1.391 (3)
C1—C2	1.401 (3)	C10—H10	0.9500
C1—C6	1.405 (3)	C11—C12	1.385 (3)
C2—C3	1.411 (3)	C11—H11	0.9500
C3—C4	1.379 (3)	C12—H12	0.9500
C3—H3	0.9500

C7—Te1—C1	96.36 (7)	C3—C4—C5	120.7 (2)
C7—Te1—H1N1	113.5 (6)	C3—C4—H4	119.7
C1—Te1—H1N1	59.9 (5)	C5—C4—H4	119.7
C7—Te1—H2N1	59.9 (4)	C4—C5—C6	119.0 (2)
C1—Te1—H2N1	66.3 (5)	C4—C5—H5	120.5
H1N1—Te1—H2N1	53.7 (7)	C6—C5—H5	120.5
C2—N1—N2	84.56 (12)	C5—C6—C1	121.5 (2)
C2—N1—H1N1	115 (2)	C5—C6—H6	119.2
N2—N1—H1N1	78 (2)	C1—C6—H6	119.2
C2—N1—H1N2	111 (3)	C12—C7—C8	119.93 (18)
N2—N1—H1N2	148 (3)	C12—C7—Te1	117.65 (14)
H1N1—N1—H1N2	116 (3)	C8—C7—Te1	122.39 (14)
C8—N2—N1	123.77 (13)	N2—C8—C9	119.47 (19)
C8—N2—H2N1	120 (2)	N2—C8—C7	122.63 (18)
N1—N2—H2N1	4 (2)	C9—C8—C7	117.86 (18)
C8—N2—H2N2	116 (2)	C10—C9—C8	121.5 (2)
N1—N2—H2N2	111 (2)	C10—C9—H9	119.2
H2N1—N2—H2N2	115 (3)	C8—C9—H9	119.2
C2—C1—C6	119.40 (18)	C9—C10—C11	120.33 (19)
C2—C1—Te1	121.91 (15)	C9—C10—H10	119.8
C6—C1—Te1	118.68 (15)	C11—C10—H10	119.8
N1—C2—C1	122.51 (19)	C12—C11—C10	119.02 (19)
N1—C2—C3	119.3 (2)	C12—C11—H11	120.5
C1—C2—C3	118.08 (19)	C10—C11—H11	120.5
C4—C3—C2	121.4 (2)	C11—C12—C7	121.29 (19)
C4—C3—H3	119.3	C11—C12—H12	119.4
C2—C3—H3	119.3	C7—C12—H12	119.4

N2—N1—C2—C1	55.43 (18)	N1—N2—C8—C9	163.18 (15)
N2—N1—C2—C3	−120.52 (17)	N1—N2—C8—C7	−19.5 (3)
C6—C1—C2—N1	−175.84 (19)	C12—C7—C8—N2	−175.81 (19)
Te1—C1—C2—N1	5.1 (3)	Te1—C7—C8—N2	1.9 (3)
C6—C1—C2—C3	0.2 (3)	C12—C7—C8—C9	1.6 (3)
Te1—C1—C2—C3	−178.87 (14)	Te1—C7—C8—C9	179.30 (14)
N1—C2—C3—C4	175.8 (2)	N2—C8—C9—C10	176.0 (2)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C9—C10	−1.5 (3)
C2—C3—C4—C5	0.0 (3)	C8—C9—C10—C11	−0.1 (3)
C3—C4—C5—C6	0.4 (3)	C9—C10—C11—C12	1.6 (3)
C4—C5—C6—C1	−0.6 (3)	C10—C11—C12—C7	−1.5 (3)
C2—C1—C6—C5	0.3 (3)	C8—C7—C12—C11	−0.1 (3)
Te1—C1—C6—C5	179.34 (16)	Te1—C7—C12—C11	−177.97 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N1···N1	0.85 (2)	2.65 (2)	3.490 (3)	175 (3)
N2—H2N2···N1ⁱ	0.86 (2)	2.43 (2)	3.253 (3)	162 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

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Bis(2-nitro­phen­yl) selenide, bis­(2-amino­phen­yl) selenide and bis­(2-amino­phen­yl) telluride: structural and theoretical analysis

Supporting information

Bis(2-nitrophenyl) selenide, bis(2-aminophenyl) selenide and bis(2-aminophenyl) telluride: structural and theoretical analysis