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

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].

Computing details

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)

Crystal data

C12H8N2O4Se	Z = 2
Mr = 323.16	F(000) = 320
Triclinic, P1	Dx = 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) Å^3	0.24 × 0.20 × 0.13 mm

Data collection

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	Rint = 0.041
ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015\)	h = −10→10
Tmin = 0.595, Tmax = 1.000	k = −10→10
5993 measured reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 0.6023P] where P = (Fo^2 + 2Fc^2)/3
2886 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 1.18 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.95 (3)	2.62 (3)	3.243 (3)	123 (2)
C8—H8···O4^ii	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)

Crystal data

C12H12N2Se	F(000) = 528
Mr = 263.20	Dx = 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) Å^3	Prism, colorless
Z = 4	0.30 × 0.28 × 0.17 mm

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: mixed
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 1.7514P] where P = (Fo^2 + 2Fc^2)/3
3168 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 1.58 e Å^−3
4 restraints	Δρmin = −0.83 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2^i	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···Se1^ii	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)

Crystal data

C12H12N2Te	Z = 2
Mr = 311.84	F(000) = 300
Triclinic, P1	Dx = 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) Å^3	0.21 × 0.16 × 0.12 mm

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.020	Hydrogen site location: mixed
wR(F^2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0215P)^2 + 0.5277P] where P = (Fo^2 + 2Fc^2)/3
2976 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 1.27 e Å^−3
4 restraints	Δρmin = −1.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···N1^i	0.86 (2)	2.43 (2)	3.253 (3)	162 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.