Two isomeric
trans-4-aminoazoxybenzenes,
trans-1-(4-aminophenyl)-2-phenyldiazene 2-oxide (α, C
12H
11N
3O) and
trans-2-(4-aminophenyl)-1-phenyldiazene 2-oxide (β, C
12H
11N
3O), have been characterized by X-ray diffraction. The α isomer is almost planar, having torsion angles along the C
aryl—N bonds of only 4.9 (2) and 8.0 (2)°. The relatively short C
aryl—N bond to the non-oxidized site of the azoxy group [1.401 (2) Å], together with the significant quinoid deformation of the respective phenyl ring, is evidence of conjugation between the aromatic sextet and the π-electron system of the azoxy group. The geometry of the β isomer is different. The non-substituted phenyl ring is twisted with respect to the NNO plane by
ca 50°, whereas the substituted ring is almost coplanar with the NNO plane. The non-oxidized N atom in the β isomer has increased
sp3 character, which leads to a decrease in the N—N—C bond angle to 116.8 (2)°, in contrast with 120.9 (1)° for the α isomer. The deformation of the C—C—C angles (1–2°) in the phenyl rings at the substitution positions is evidence of the different character of the oxidized and non-oxidized N atoms of the azoxy group. In the crystal structures, molecules of both isomers are arranged in chains connected by weak N—H
O (α and β) and N—H
N (β) hydrogen bonds.
Supporting information
CCDC references: 163934; 163935
For both compounds, data collection: Kuma Diffraction Software (Kuma, 1998); cell refinement: Kuma Diffraction Software; data reduction: Kuma Diffraction Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
(I)
trans-1-(4-aminophenyl)-2-phenyldiazene 2-oxide
top
Crystal data top
C12H11N3O | F(000) = 448 |
Mr = 213.24 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 5.733 (1) Å | Cell parameters from 28 reflections |
b = 11.602 (2) Å | θ = 8–13° |
c = 16.038 (3) Å | µ = 0.09 mm−1 |
β = 93.16 (3)° | T = 293 K |
V = 1065.1 (3) Å3 | Prism, orange |
Z = 4 | 0.7 × 0.6 × 0.2 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 3.1° |
Graphite monochromator | h = −6→6 |
ω/θ scans | k = −13→0 |
4164 measured reflections | l = −19→19 |
1888 independent reflections | 2 standard reflections every 50 reflections |
1480 reflections with I > 2σ(I) | intensity decay: 0.7% |
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)] = 0.037 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.101 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0736P)2 + 0.1764P] where P = (Fo2 + 2Fc2)/3 |
1888 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 0.2548 (2) | 0.30930 (13) | 0.11594 (9) | 0.0966 (6) | |
N1 | 0.0834 (2) | 0.31672 (11) | 0.06282 (7) | 0.0485 (3) | |
N2 | −0.0788 (2) | 0.39013 (10) | 0.06244 (7) | 0.0445 (3) | |
N3 | −0.2063 (3) | 0.73408 (15) | 0.29746 (10) | 0.0697 (5) | |
C1 | −0.0835 (2) | 0.47497 (12) | 0.12451 (8) | 0.0410 (3) | |
C1' | 0.0665 (2) | 0.23009 (13) | −0.00289 (9) | 0.0462 (4) | |
C2 | 0.0850 (3) | 0.50300 (13) | 0.18770 (10) | 0.0492 (4) | |
C2' | 0.2487 (3) | 0.15477 (17) | −0.00918 (12) | 0.0669 (5) | |
C3 | 0.0439 (3) | 0.58957 (14) | 0.24344 (10) | 0.0518 (4) | |
C3' | 0.2361 (4) | 0.07247 (18) | −0.07149 (13) | 0.0765 (6) | |
C4 | −0.1636 (3) | 0.65113 (13) | 0.23948 (9) | 0.0479 (4) | |
C4' | 0.0450 (4) | 0.06598 (17) | −0.12593 (13) | 0.0733 (5) | |
C5 | −0.3316 (3) | 0.62343 (14) | 0.17657 (10) | 0.0515 (4) | |
C5' | −0.1347 (4) | 0.14192 (18) | −0.11885 (13) | 0.0763 (6) | |
C6 | −0.2911 (3) | 0.53820 (14) | 0.12043 (9) | 0.0486 (4) | |
C6' | −0.1258 (3) | 0.22458 (16) | −0.05703 (11) | 0.0611 (5) | |
H2 | 0.230 (3) | 0.4641 (15) | 0.1919 (10) | 0.061 (5)* | |
H2' | 0.382 (4) | 0.1598 (17) | 0.0265 (12) | 0.081 (6)* | |
H3 | 0.163 (3) | 0.6091 (15) | 0.2838 (10) | 0.062 (5)* | |
H3' | 0.360 (4) | 0.0215 (19) | −0.0781 (13) | 0.090 (7)* | |
H4' | 0.037 (3) | 0.0071 (18) | −0.1683 (12) | 0.085 (6)* | |
H5 | −0.480 (3) | 0.6657 (16) | 0.1726 (10) | 0.068 (5)* | |
H5' | −0.271 (4) | 0.138 (2) | −0.1561 (13) | 0.100 (7)* | |
H6 | −0.411 (3) | 0.5189 (14) | 0.0768 (10) | 0.062 (5)* | |
H6' | −0.258 (3) | 0.2780 (17) | −0.0485 (11) | 0.081 (6)* | |
H31 | −0.084 (4) | 0.7602 (18) | 0.3269 (14) | 0.093 (7)* | |
H32 | −0.333 (4) | 0.779 (2) | 0.2878 (13) | 0.099 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0827 (9) | 0.0949 (11) | 0.1060 (11) | 0.0442 (8) | −0.0514 (8) | −0.0425 (9) |
N1 | 0.0478 (7) | 0.0473 (7) | 0.0495 (7) | 0.0051 (6) | −0.0058 (5) | 0.0016 (6) |
N2 | 0.0466 (7) | 0.0443 (7) | 0.0424 (6) | 0.0041 (5) | 0.0003 (5) | 0.0041 (5) |
N3 | 0.0648 (10) | 0.0759 (11) | 0.0679 (10) | 0.0066 (9) | −0.0021 (8) | −0.0275 (8) |
C1 | 0.0451 (7) | 0.0398 (7) | 0.0380 (7) | −0.0018 (6) | 0.0014 (5) | 0.0042 (6) |
C1' | 0.0520 (8) | 0.0407 (8) | 0.0463 (8) | 0.0010 (6) | 0.0055 (6) | 0.0023 (6) |
C2 | 0.0435 (8) | 0.0496 (8) | 0.0539 (9) | 0.0023 (7) | −0.0036 (6) | 0.0004 (7) |
C2' | 0.0644 (11) | 0.0652 (11) | 0.0703 (11) | 0.0177 (9) | −0.0037 (9) | −0.0084 (9) |
C3 | 0.0477 (8) | 0.0555 (9) | 0.0509 (8) | −0.0027 (7) | −0.0080 (7) | −0.0048 (7) |
C3' | 0.0791 (13) | 0.0674 (12) | 0.0831 (13) | 0.0256 (10) | 0.0062 (10) | −0.0152 (11) |
C4 | 0.0495 (8) | 0.0479 (9) | 0.0464 (8) | −0.0029 (7) | 0.0051 (6) | −0.0020 (7) |
C4' | 0.0845 (13) | 0.0639 (12) | 0.0717 (12) | 0.0073 (10) | 0.0053 (10) | −0.0203 (10) |
C5 | 0.0460 (8) | 0.0534 (9) | 0.0546 (9) | 0.0065 (7) | −0.0006 (7) | −0.0029 (7) |
C5' | 0.0739 (12) | 0.0764 (13) | 0.0766 (13) | 0.0088 (10) | −0.0127 (10) | −0.0251 (11) |
C6 | 0.0460 (8) | 0.0527 (9) | 0.0463 (8) | 0.0024 (7) | −0.0060 (6) | −0.0007 (7) |
C6' | 0.0593 (10) | 0.0589 (10) | 0.0643 (10) | 0.0096 (8) | −0.0039 (8) | −0.0115 (8) |
Geometric parameters (Å, º) top
O1—N1 | 1.268 (2) | C4'—C5' | 1.365 (3) |
N1—N2 | 1.261 (2) | C5—C6 | 1.366 (2) |
N1—C1' | 1.456 (2) | C5'—C6' | 1.378 (2) |
N2—C1 | 1.401 (2) | N3—H32 | 0.90 (2) |
N3—C4 | 1.369 (2) | N3—H31 | 0.88 (2) |
C1—C6 | 1.396 (2) | C2—H2 | 0.95 (2) |
C1—C2 | 1.399 (2) | C2'—H2' | 0.93 (2) |
C1'—C6' | 1.367 (2) | C3—H3 | 0.94 (2) |
C1'—C2' | 1.370 (2) | C3'—H3' | 0.93 (2) |
C2—C3 | 1.374 (2) | C4'—H4' | 0.96 (2) |
C2'—C3' | 1.381 (3) | C5—H5 | 0.98 (2) |
C3—C4 | 1.386 (2) | C5'—H5' | 0.96 (2) |
C3'—C4' | 1.365 (3) | C6—H6 | 0.98 (2) |
C4—C5 | 1.393 (2) | C6'—H6' | 0.99 (2) |
| | | |
N2—N1—O1 | 126.4 (1) | C4—N3—H32 | 117 (1) |
N2—N1—C1' | 116.3 (1) | C4—N3—H31 | 116 (1) |
O1—N1—C1' | 117.2 (1) | H32—N3—H31 | 121 (2) |
N1—N2—C1 | 120.9 (1) | C3—C2—H2 | 119 (1) |
C6—C1—C2 | 117.7 (1) | C1—C2—H2 | 121 (1) |
C6—C1—N2 | 112.7 (1) | C1'—C2'—H2' | 121 (1) |
C2—C1—N2 | 129.7 (1) | C3'—C2'—H2' | 120 (1) |
C6'—C1'—C2' | 121.0 (2) | C2—C3—H3 | 119 (1) |
C6'—C1'—N1 | 120.7 (1) | C4—C3—H3 | 120 (1) |
C2'—C1'—N1 | 118.2 (1) | C4'—C3'—H3' | 119 (1) |
C3—C2—C1 | 120.3 (1) | C2'—C3'—H3' | 121 (1) |
C1'—C2'—C3' | 119.0 (2) | C3'—C4'—H4' | 120 (1) |
C2—C3—C4 | 121.6 (1) | C5'—C4'—H4' | 121 (1) |
C4'—C3'—C2' | 120.6 (2) | C6—C5—H5 | 120 (1) |
N3—C4—C3 | 121.0 (1) | C4—C5—H5 | 120 (1) |
N3—C4—C5 | 120.8 (1) | C4'—C5'—H5' | 121 (1) |
C3—C4—C5 | 118.1 (1) | C6'—C5'—H5' | 119 (1) |
C3'—C4'—C5' | 119.6 (2) | C5—C6—H6 | 120 (1) |
C6—C5—C4 | 120.6 (1) | C1—C6—H6 | 118 (1) |
C4'—C5'—C6' | 120.7 (2) | C1'—C6'—H6' | 119 (1) |
C5—C6—C1 | 121.7 (1) | C5'—C6'—H6' | 122 (1) |
C1'—C6'—C5' | 119.1 (2) | | |
| | | |
O1—N1—N2—C1 | 0.0 (2) | C1'—C2'—C3'—C4' | −0.1 (3) |
C1'—N1—N2—C1 | 177.9 (1) | C2—C3—C4—N3 | 177.3 (2) |
N1—N2—C1—C6 | −171.8 (1) | C2—C3—C4—C5 | −0.4 (2) |
N1—N2—C1—C2 | 7.8 (2) | C2'—C3'—C4'—C5' | 0.3 (3) |
N2—N1—C1'—C6' | −5.2 (2) | N3—C4—C5—C6 | −178.0 (2) |
O1—N1—C1'—C6' | 172.9 (2) | C3—C4—C5—C6 | −0.3 (2) |
N2—N1—C1'—C2' | 174.5 (1) | C3'—C4'—C5'—C6' | −0.4 (3) |
O1—N1—C1'—C2' | −7.4 (2) | C4—C5—C6—C1 | 1.0 (2) |
C6—C1—C2—C3 | 0.3 (2) | C2—C1—C6—C5 | −1.0 (2) |
N2—C1—C2—C3 | −179.3 (1) | N2—C1—C6—C5 | 178.7 (1) |
C6'—C1'—C2'—C3' | 0.1 (3) | C2'—C1'—C6'—C5' | −0.2 (3) |
N1—C1'—C2'—C3' | −179.6 (2) | N1—C1'—C6'—C5' | 179.5 (2) |
C1—C2—C3—C4 | 0.3 (2) | C4'—C5'—C6'—C1' | 0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H31···O1i | 0.88 (2) | 2.13 (2) | 2.999 (2) | 171 (2) |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
(II)
trans-2-(4-aminophenyl)-1-phenyldiazene 2-oxide
top
Crystal data top
C12H11N3O | F(000) = 224 |
Mr = 213.24 | Dx = 1.333 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.764 (2) Å | Cell parameters from 25 reflections |
b = 6.103 (1) Å | θ = 8–12° |
c = 10.791 (2) Å | µ = 0.09 mm−1 |
β = 112.97 (3)° | T = 293 K |
V = 531.4 (2) Å3 | Prism, yellow |
Z = 2 | 0.6 × 0.4 × 0.4 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 30.1°, θmin = 2.1° |
Graphite monochromator | h = −11→11 |
ω/θ scans | k = −7→7 |
2506 measured reflections | l = −11→15 |
1432 independent reflections | 2 standard reflections every 50 reflections |
973 reflections with I > 2σ(I) | intensity decay: 0.03% |
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)] = 0.031 | Hydrogen site location: dimap |
wR(F2) = 0.096 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0451P] where P = (Fo2 + 2Fc2)/3 |
1432 reflections | (Δ/σ)max = 0.081 |
189 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.13 e Å−3 |
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 | Uiso*/Ueq | |
O1 | −0.13808 (19) | 0.3189 (3) | 0.19579 (18) | 0.0615 (5) | |
N1 | −0.0237 (2) | 0.4585 (3) | 0.22602 (18) | 0.0441 (5) | |
N2 | −0.0175 (2) | 0.6360 (3) | 0.2885 (2) | 0.0534 (5) | |
N3 | 0.5030 (3) | 0.2624 (5) | 0.0737 (3) | 0.0645 (7) | |
C1 | 0.1115 (3) | 0.4122 (4) | 0.1843 (2) | 0.0432 (5) | |
C2 | 0.1128 (3) | 0.2151 (4) | 0.1242 (3) | 0.0514 (6) | |
C3 | 0.2433 (3) | 0.1629 (5) | 0.0886 (3) | 0.0550 (6) | |
C4 | 0.3736 (3) | 0.3084 (5) | 0.1129 (2) | 0.0501 (6) | |
C5 | 0.3690 (3) | 0.5085 (5) | 0.1727 (3) | 0.0539 (7) | |
C6 | 0.2387 (3) | 0.5618 (5) | 0.2087 (2) | 0.0507 (6) | |
C1' | −0.1405 (3) | 0.6676 (4) | 0.3421 (2) | 0.0479 (5) | |
C2' | −0.1675 (3) | 0.5181 (5) | 0.4271 (3) | 0.0577 (7) | |
C3' | −0.2678 (4) | 0.5751 (6) | 0.4941 (3) | 0.0686 (8) | |
C4' | −0.3439 (4) | 0.7748 (6) | 0.4745 (3) | 0.0693 (9) | |
C5' | −0.3203 (4) | 0.9209 (6) | 0.3882 (4) | 0.0710 (8) | |
C6' | −0.2163 (4) | 0.8694 (5) | 0.3225 (3) | 0.0601 (7) | |
H2 | 0.032 (3) | 0.113 (5) | 0.113 (3) | 0.064 (9)* | |
H3 | 0.246 (3) | 0.030 (6) | 0.049 (3) | 0.059 (8)* | |
H5 | 0.466 (3) | 0.602 (5) | 0.204 (3) | 0.069 (8)* | |
H6 | 0.239 (3) | 0.689 (6) | 0.265 (3) | 0.072 (9)* | |
H32 | 0.604 (4) | 0.331 (7) | 0.132 (3) | 0.076 (8)* | |
H31 | 0.508 (4) | 0.136 (6) | 0.059 (3) | 0.058 (10)* | |
H2' | −0.115 (3) | 0.383 (6) | 0.444 (3) | 0.067 (9)* | |
H3' | −0.282 (4) | 0.477 (7) | 0.560 (3) | 0.089 (11)* | |
H4' | −0.415 (3) | 0.814 (6) | 0.520 (3) | 0.077 (9)* | |
H5' | −0.378 (4) | 1.058 (7) | 0.373 (3) | 0.079 (10)* | |
H6' | −0.195 (3) | 0.966 (6) | 0.276 (3) | 0.061 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0489 (9) | 0.0570 (11) | 0.0853 (11) | −0.0192 (9) | 0.0335 (8) | −0.0148 (10) |
N1 | 0.0379 (9) | 0.0423 (11) | 0.0519 (10) | −0.0064 (8) | 0.0173 (7) | 0.0017 (9) |
N2 | 0.0512 (11) | 0.0436 (13) | 0.0714 (13) | −0.0083 (10) | 0.0306 (10) | −0.0073 (11) |
N3 | 0.0477 (12) | 0.076 (2) | 0.0753 (16) | −0.0029 (13) | 0.0297 (11) | −0.0092 (16) |
C1 | 0.0381 (10) | 0.0450 (14) | 0.0465 (11) | −0.0046 (10) | 0.0164 (9) | 0.0016 (10) |
C2 | 0.0416 (12) | 0.0506 (16) | 0.0610 (13) | −0.0112 (11) | 0.0189 (11) | −0.0067 (12) |
C3 | 0.0510 (13) | 0.0539 (16) | 0.0618 (15) | −0.0038 (13) | 0.0238 (11) | −0.0089 (14) |
C4 | 0.0390 (11) | 0.0645 (17) | 0.0454 (12) | −0.0027 (12) | 0.0148 (9) | 0.0009 (12) |
C5 | 0.0453 (12) | 0.0607 (18) | 0.0590 (14) | −0.0182 (12) | 0.0239 (11) | −0.0085 (13) |
C6 | 0.0497 (13) | 0.0490 (14) | 0.0559 (14) | −0.0141 (12) | 0.0233 (11) | −0.0070 (12) |
C1' | 0.0410 (11) | 0.0449 (13) | 0.0564 (13) | −0.0065 (10) | 0.0176 (10) | −0.0044 (12) |
C2' | 0.0563 (14) | 0.0546 (17) | 0.0615 (15) | 0.0045 (13) | 0.0221 (11) | 0.0091 (13) |
C3' | 0.0700 (17) | 0.083 (2) | 0.0581 (16) | −0.0013 (17) | 0.0303 (14) | 0.0061 (16) |
C4' | 0.0630 (16) | 0.085 (2) | 0.0665 (16) | −0.0047 (16) | 0.0324 (13) | −0.0196 (18) |
C5' | 0.0624 (17) | 0.0572 (19) | 0.096 (2) | 0.0045 (15) | 0.0336 (15) | −0.0151 (17) |
C6' | 0.0605 (15) | 0.0435 (16) | 0.0814 (19) | −0.0042 (12) | 0.0332 (14) | −0.0008 (15) |
Geometric parameters (Å, º) top
O1—N1 | 1.257 (3) | C3'—C4' | 1.366 (5) |
N1—N2 | 1.266 (3) | C4'—C5' | 1.362 (5) |
N1—C1 | 1.450 (3) | C5'—C6' | 1.392 (4) |
N2—C1' | 1.421 (3) | N3—H32 | 0.95 (3) |
N3—C4 | 1.385 (3) | N3—H31 | 0.81 (2) |
C1—C2 | 1.369 (3) | C2—H2 | 0.93 (2) |
C1—C6 | 1.385 (3) | C3—H3 | 0.92 (3) |
C2—C3 | 1.379 (4) | C5—H5 | 0.97 (2) |
C3—C4 | 1.388 (4) | C6—H6 | 0.98 (3) |
C4—C5 | 1.389 (4) | C2'—H2' | 0.93 (3) |
C5—C6 | 1.381 (3) | C3'—H3' | 0.98 (3) |
C1'—C2' | 1.378 (4) | C4'—H4' | 0.95 (2) |
C1'—C6' | 1.375 (4) | C5'—H5' | 0.96 (3) |
C2'—C3' | 1.383 (4) | C6'—H6' | 0.87 (2) |
| | | |
O1—N1—N2 | 125.6 (2) | C4—N3—H32 | 112 (2) |
O1—N1—C1 | 116.9 (2) | C4—N3—H31 | 112 (2) |
N2—N1—C1 | 117.5 (2) | H32—N3—H31 | 118 (3) |
N1—N2—C1' | 116.8 (2) | C1—C2—H2 | 120 (1) |
C2—C1—C6 | 121.0 (2) | C3—C2—H2 | 121 (1) |
C2—C1—N1 | 118.5 (2) | C2—C3—H3 | 121 (1) |
C6—C1—N1 | 120.5 (2) | C4—C3—H3 | 119 (1) |
C1—C2—C3 | 119.7 (2) | C6—C5—H5 | 118 (1) |
C2—C3—C4 | 120.7 (3) | C4—C5—H5 | 120 (1) |
N3—C4—C5 | 119.8 (3) | C5—C6—H6 | 125 (1) |
N3—C4—C3 | 121.5 (3) | C1—C6—H6 | 116 (1) |
C5—C4—C3 | 118.6 (2) | C1'—C2'—H2' | 120 (1) |
C6—C5—C4 | 121.0 (2) | C3'—C2'—H2' | 120 (1) |
C5—C6—C1 | 118.9 (2) | C4'—C3'—H3' | 120 (2) |
C2'—C1'—C6' | 119.8 (3) | C2'—C3'—H3' | 120 (2) |
C2'—C1'—N2 | 122.4 (2) | C5'—C4'—H4' | 119 (2) |
C6'—C1'—N2 | 117.1 (2) | C3'—C4'—H4' | 121 (2) |
C1'—C2'—C3' | 119.4 (3) | C4'—C5'—H5' | 119 (2) |
C4'—C3'—C2' | 121.0 (3) | C6'—C5'—H5' | 121 (2) |
C5'—C4'—C3' | 119.7 (3) | C1'—C6'—H6' | 120 (2) |
C4'—C5'—C6' | 120.3 (3) | C5'—C6'—H6' | 120 (2) |
C1'—C6'—C5' | 119.8 (3) | | |
| | | |
O1—N1—N2—C1' | 7.7 (3) | C4—C5—C6—C1 | 0.0 (4) |
C1—N1—N2—C1' | −173.0 (2) | C2—C1—C6—C5 | −0.7 (4) |
O1—N1—C1—C2 | −4.7 (3) | N1—C1—C6—C5 | 177.3 (2) |
N2—N1—C1—C2 | 175.9 (2) | N1—N2—C1'—C2' | 54.6 (3) |
O1—N1—C1—C6 | 177.3 (2) | N1—N2—C1'—C6' | −134.9 (2) |
N2—N1—C1—C6 | −2.1 (3) | C6'—C1'—C2'—C3' | −1.5 (4) |
C6—C1—C2—C3 | 0.7 (4) | N2—C1'—C2'—C3' | 168.8 (2) |
N1—C1—C2—C3 | −177.3 (2) | C1'—C2'—C3'—C4' | 1.8 (4) |
C1—C2—C3—C4 | 0.0 (4) | C2'—C3'—C4'—C5' | −0.3 (5) |
C2—C3—C4—N3 | −177.7 (3) | C3'—C4'—C5'—C6' | −1.5 (5) |
C2—C3—C4—C5 | −0.6 (4) | C2'—C1'—C6'—C5' | −0.3 (4) |
N3—C4—C5—C6 | 177.8 (3) | N2—C1'—C6'—C5' | −171.1 (2) |
C3—C4—C5—C6 | 0.6 (4) | C4'—C5'—C6'—C1' | 1.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H32···O1i | 0.96 (3) | 2.09 (3) | 2.918 (3) | 143 (3) |
N3—H31···N3ii | 0.79 (3) | 2.68 (3) | 3.432 (2) | 161 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z. |