There are two independent molecules, A and B, in the title compound, C16H18N4O4, and the asymmetric unit consists of one molecule A and one half-molecule B; a twofold axis runs through the centre of the N-N bond of molecule B. The crystal structure is stabilized mainly by van der Waals forces.
Supporting information
CCDC reference: 285500
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.047
- wR factor = 0.107
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N5 - C23 .. 8.56 su
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.85
PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C18 .. 5.11 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 .. 5.74 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2550
Count of symmetry unique reflns 2551
Completeness (_total/calc) 99.96%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N,
N'-Diethyl-4,4'-dinitrohydrazobenzene
top
Crystal data top
C16H18N4O4 | F(000) = 1044 |
Mr = 330.34 | Dx = 1.343 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 60 reflections |
a = 7.8212 (16) Å | θ = 1.8–12.5° |
b = 46.154 (4) Å | µ = 0.10 mm−1 |
c = 6.7885 (8) Å | T = 295 K |
V = 2450.5 (6) Å3 | Prism, red |
Z = 6 | 0.4 × 0.4 × 0.2 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.070 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.8° |
Graphite monochromator | h = −9→9 |
ω scans | k = −54→54 |
6045 measured reflections | l = −8→8 |
2550 independent reflections | 3 standard reflections every 97 reflections |
1594 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.001P)2 + P] where P = (Fo2 + 2Fc2)/3 |
2550 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 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 | 1.2281 (5) | 0.18667 (8) | 0.7748 (7) | 0.0920 (13) | |
O2 | 0.9552 (5) | 0.18962 (7) | 0.7215 (5) | 0.0701 (10) | |
O3 | 1.1594 (5) | 0.11903 (8) | 0.8338 (7) | 0.0874 (12) | |
O4 | 1.0551 (5) | 0.07597 (7) | 0.8584 (6) | 0.0897 (12) | |
O5 | 0.1050 (4) | 0.02616 (7) | 0.3721 (8) | 0.1032 (16) | |
O6 | 0.0890 (5) | 0.07220 (7) | 0.3956 (6) | 0.0867 (12) | |
N1 | 0.8269 (5) | 0.17853 (7) | 1.1264 (5) | 0.0486 (9) | |
N2 | 0.9069 (5) | 0.15309 (6) | 1.0533 (5) | 0.0484 (9) | |
N3 | 1.0841 (6) | 0.19364 (8) | 0.8239 (7) | 0.0626 (11) | |
N4 | 1.0409 (5) | 0.10215 (9) | 0.8367 (6) | 0.0620 (11) | |
N5 | 0.4406 (5) | 0.01142 (6) | 0.5341 (5) | 0.0536 (10) | |
N6 | 0.1678 (5) | 0.04976 (9) | 0.3700 (7) | 0.0650 (11) | |
C1 | 0.9351 (6) | 0.20235 (8) | 1.1463 (6) | 0.0495 (11) | |
C2 | 1.0632 (6) | 0.20944 (8) | 1.0108 (7) | 0.0536 (12) | |
C3 | 1.1743 (7) | 0.23244 (9) | 1.0352 (8) | 0.0662 (14) | |
H3 | 1.2610 | 0.2356 | 0.9439 | 0.079* | |
C4 | 1.1566 (8) | 0.25056 (10) | 1.1939 (9) | 0.0801 (17) | |
H4 | 1.2284 | 0.2665 | 1.2094 | 0.096* | |
C5 | 1.0311 (8) | 0.24478 (10) | 1.3294 (8) | 0.0753 (16) | |
H5 | 1.0180 | 0.2570 | 1.4374 | 0.090* | |
C6 | 0.9233 (7) | 0.22107 (8) | 1.3086 (7) | 0.0618 (13) | |
H6 | 0.8412 | 0.2175 | 1.4046 | 0.074* | |
C7 | 0.8112 (6) | 0.13925 (8) | 0.9041 (6) | 0.0443 (10) | |
C8 | 0.8675 (6) | 0.11420 (9) | 0.8068 (7) | 0.0505 (11) | |
C9 | 0.7706 (6) | 0.09950 (9) | 0.6694 (7) | 0.0594 (13) | |
H9 | 0.8117 | 0.0825 | 0.6124 | 0.071* | |
C10 | 0.6112 (6) | 0.11027 (10) | 0.6172 (7) | 0.0605 (13) | |
H10 | 0.5431 | 0.1005 | 0.5267 | 0.073* | |
C11 | 0.5553 (6) | 0.13579 (9) | 0.7021 (7) | 0.0564 (12) | |
H11 | 0.4509 | 0.1436 | 0.6636 | 0.068* | |
C12 | 0.6515 (6) | 0.14984 (9) | 0.8427 (6) | 0.0526 (11) | |
H12 | 0.6096 | 0.1668 | 0.8985 | 0.063* | |
C13 | 0.6882 (6) | 0.17443 (9) | 1.2737 (7) | 0.0615 (13) | |
H13A | 0.7361 | 0.1763 | 1.4049 | 0.074* | |
H13B | 0.6428 | 0.1550 | 1.2608 | 0.074* | |
C14 | 0.5432 (7) | 0.19596 (10) | 1.2512 (8) | 0.0766 (16) | |
H14A | 0.4581 | 0.1923 | 1.3501 | 0.115* | |
H14B | 0.4929 | 0.1939 | 1.1229 | 0.115* | |
H14C | 0.5867 | 0.2153 | 1.2664 | 0.115* | |
C15 | 0.9803 (6) | 0.13491 (9) | 1.2135 (7) | 0.0584 (12) | |
H15A | 0.9970 | 0.1154 | 1.1646 | 0.070* | |
H15B | 0.8996 | 0.1340 | 1.3217 | 0.070* | |
C16 | 1.1475 (7) | 0.14636 (9) | 1.2883 (9) | 0.0836 (18) | |
H16A | 1.1901 | 0.1338 | 1.3898 | 0.125* | |
H16B | 1.1311 | 0.1655 | 1.3409 | 0.125* | |
H16C | 1.2284 | 0.1471 | 1.1820 | 0.125* | |
C18 | 0.3525 (6) | 0.05239 (9) | 0.3234 (7) | 0.0510 (11) | |
C17 | 0.4751 (6) | 0.03327 (9) | 0.3972 (7) | 0.0478 (11) | |
C22 | 0.6404 (6) | 0.03630 (9) | 0.3168 (8) | 0.0581 (13) | |
H22 | 0.7260 | 0.0235 | 0.3557 | 0.070* | |
C21 | 0.6785 (7) | 0.05771 (9) | 0.1817 (8) | 0.0677 (14) | |
H21 | 0.7892 | 0.0592 | 0.1327 | 0.081* | |
C20 | 0.5547 (7) | 0.07711 (10) | 0.1177 (8) | 0.0657 (14) | |
H20 | 0.5812 | 0.0916 | 0.0276 | 0.079* | |
C19 | 0.3918 (6) | 0.07424 (9) | 0.1913 (8) | 0.0596 (13) | |
H19 | 0.3070 | 0.0871 | 0.1519 | 0.071* | |
C23 | 0.3415 (7) | 0.01775 (11) | 0.7190 (10) | 0.0856 (17) | |
H23A | 0.4204 | 0.0214 | 0.8264 | 0.103* | |
H23B | 0.2730 | 0.0350 | 0.6999 | 0.103* | |
C24 | 0.2283 (8) | −0.00690 (13) | 0.7707 (10) | 0.120 (2) | |
H24A | 0.1674 | −0.0025 | 0.8898 | 0.180* | |
H24B | 0.2960 | −0.0240 | 0.7900 | 0.180* | |
H24C | 0.1481 | −0.0101 | 0.6659 | 0.180* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.067 (3) | 0.108 (3) | 0.100 (3) | 0.004 (2) | 0.024 (3) | −0.014 (3) |
O2 | 0.086 (3) | 0.076 (2) | 0.0490 (19) | −0.007 (2) | −0.001 (2) | 0.0062 (17) |
O3 | 0.052 (2) | 0.095 (2) | 0.115 (3) | −0.004 (2) | 0.010 (3) | 0.007 (3) |
O4 | 0.091 (3) | 0.068 (2) | 0.110 (3) | 0.020 (2) | −0.013 (3) | −0.006 (2) |
O5 | 0.052 (2) | 0.068 (2) | 0.190 (5) | −0.0106 (18) | −0.002 (3) | 0.014 (3) |
O6 | 0.069 (2) | 0.083 (2) | 0.108 (3) | 0.026 (2) | 0.018 (3) | 0.008 (2) |
N1 | 0.056 (2) | 0.0481 (18) | 0.041 (2) | −0.0051 (19) | 0.002 (2) | 0.0003 (17) |
N2 | 0.059 (2) | 0.0417 (17) | 0.0448 (19) | 0.0012 (18) | −0.005 (2) | 0.0008 (17) |
N3 | 0.070 (3) | 0.057 (2) | 0.060 (3) | −0.006 (2) | 0.007 (3) | 0.003 (2) |
N4 | 0.057 (3) | 0.066 (2) | 0.062 (3) | 0.003 (2) | 0.002 (2) | −0.006 (2) |
N5 | 0.052 (2) | 0.0470 (19) | 0.062 (2) | 0.0108 (18) | 0.009 (2) | 0.0045 (18) |
N6 | 0.057 (2) | 0.063 (2) | 0.075 (3) | 0.004 (2) | −0.008 (3) | 0.012 (2) |
C1 | 0.055 (3) | 0.047 (2) | 0.047 (3) | −0.002 (2) | −0.008 (3) | 0.006 (2) |
C2 | 0.061 (3) | 0.047 (2) | 0.053 (3) | −0.001 (2) | 0.001 (3) | 0.005 (2) |
C3 | 0.063 (3) | 0.056 (3) | 0.080 (4) | −0.014 (3) | −0.006 (3) | 0.014 (3) |
C4 | 0.088 (4) | 0.062 (3) | 0.091 (4) | −0.022 (3) | −0.020 (4) | −0.006 (3) |
C5 | 0.097 (4) | 0.062 (3) | 0.067 (4) | −0.016 (3) | −0.015 (4) | −0.013 (3) |
C6 | 0.080 (4) | 0.056 (2) | 0.049 (3) | −0.009 (3) | −0.004 (3) | −0.005 (2) |
C7 | 0.048 (3) | 0.043 (2) | 0.042 (2) | −0.006 (2) | −0.002 (2) | 0.002 (2) |
C8 | 0.051 (3) | 0.052 (2) | 0.049 (3) | −0.005 (2) | 0.003 (3) | −0.001 (2) |
C9 | 0.063 (3) | 0.061 (3) | 0.055 (3) | −0.006 (2) | 0.006 (3) | −0.009 (3) |
C10 | 0.059 (3) | 0.073 (3) | 0.049 (3) | −0.018 (3) | −0.003 (3) | −0.005 (3) |
C11 | 0.049 (3) | 0.069 (3) | 0.051 (3) | −0.004 (2) | −0.006 (3) | 0.002 (3) |
C12 | 0.051 (3) | 0.057 (2) | 0.050 (3) | 0.001 (2) | −0.005 (3) | −0.003 (2) |
C13 | 0.070 (3) | 0.062 (3) | 0.052 (3) | −0.011 (3) | 0.011 (3) | −0.003 (2) |
C14 | 0.070 (3) | 0.083 (3) | 0.077 (4) | 0.001 (3) | 0.016 (4) | −0.017 (3) |
C15 | 0.069 (3) | 0.056 (2) | 0.051 (3) | 0.004 (2) | −0.010 (3) | 0.010 (2) |
C16 | 0.089 (4) | 0.070 (3) | 0.092 (4) | 0.005 (3) | −0.045 (4) | 0.001 (3) |
C18 | 0.045 (2) | 0.049 (2) | 0.059 (3) | −0.002 (2) | 0.002 (3) | −0.001 (2) |
C17 | 0.046 (3) | 0.049 (2) | 0.049 (3) | 0.000 (2) | −0.003 (2) | −0.004 (2) |
C22 | 0.048 (3) | 0.058 (3) | 0.069 (3) | 0.000 (2) | 0.001 (3) | −0.003 (3) |
C21 | 0.062 (3) | 0.076 (3) | 0.065 (3) | −0.011 (3) | 0.012 (3) | −0.008 (3) |
C20 | 0.071 (3) | 0.068 (3) | 0.058 (3) | −0.012 (3) | 0.004 (3) | 0.007 (3) |
C19 | 0.063 (3) | 0.055 (2) | 0.061 (3) | −0.002 (2) | −0.010 (3) | 0.005 (3) |
C23 | 0.066 (3) | 0.095 (4) | 0.096 (4) | 0.019 (3) | 0.010 (4) | 0.033 (4) |
C24 | 0.100 (5) | 0.149 (6) | 0.110 (5) | 0.009 (5) | 0.019 (5) | 0.021 (5) |
Geometric parameters (Å, º) top
O1—N3 | 1.218 (5) | C10—H10 | 0.9300 |
O2—N3 | 1.239 (5) | C11—C12 | 1.378 (6) |
O3—N4 | 1.211 (5) | C11—H11 | 0.9300 |
O4—N4 | 1.223 (4) | C12—H12 | 0.9300 |
O5—N6 | 1.195 (4) | C13—C14 | 1.516 (6) |
O6—N6 | 1.218 (4) | C13—H13A | 0.9700 |
N1—C1 | 1.394 (5) | C13—H13B | 0.9700 |
N1—N2 | 1.420 (4) | C14—H14A | 0.9600 |
N1—C13 | 1.487 (5) | C14—H14B | 0.9600 |
N2—C7 | 1.412 (5) | C14—H14C | 0.9600 |
N2—C15 | 1.489 (5) | C15—C16 | 1.499 (7) |
N3—C2 | 1.472 (6) | C15—H15A | 0.9700 |
N4—C8 | 1.480 (6) | C15—H15B | 0.9700 |
N5—C17 | 1.398 (5) | C16—H16A | 0.9600 |
N5—N5i | 1.405 (6) | C16—H16B | 0.9600 |
N5—C23 | 1.504 (7) | C16—H16C | 0.9600 |
N6—C18 | 1.484 (6) | C18—C19 | 1.384 (6) |
C1—C2 | 1.399 (6) | C18—C17 | 1.396 (6) |
C1—C6 | 1.403 (6) | C17—C22 | 1.411 (6) |
C2—C3 | 1.382 (6) | C22—C21 | 1.380 (6) |
C3—C4 | 1.371 (7) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C21—C20 | 1.388 (7) |
C4—C5 | 1.371 (7) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C20—C19 | 1.376 (7) |
C5—C6 | 1.389 (6) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C23—C24 | 1.484 (7) |
C7—C8 | 1.402 (5) | C23—H23A | 0.9700 |
C7—C12 | 1.405 (6) | C23—H23B | 0.9700 |
C8—C9 | 1.380 (6) | C24—H24A | 0.9600 |
C9—C10 | 1.388 (6) | C24—H24B | 0.9600 |
C9—H9 | 0.9300 | C24—H24C | 0.9600 |
C10—C11 | 1.382 (6) | | |
| | | |
C1—N1—N2 | 114.7 (3) | N1—C13—C14 | 113.3 (4) |
C1—N1—C13 | 118.6 (3) | N1—C13—H13A | 108.9 |
N2—N1—C13 | 116.8 (3) | C14—C13—H13A | 108.9 |
C7—N2—N1 | 113.0 (3) | N1—C13—H13B | 108.9 |
C7—N2—C15 | 118.2 (3) | C14—C13—H13B | 108.9 |
N1—N2—C15 | 112.4 (3) | H13A—C13—H13B | 107.7 |
O1—N3—O2 | 124.0 (5) | C13—C14—H14A | 109.5 |
O1—N3—C2 | 118.0 (5) | C13—C14—H14B | 109.5 |
O2—N3—C2 | 117.9 (4) | H14A—C14—H14B | 109.5 |
O3—N4—O4 | 124.6 (4) | C13—C14—H14C | 109.5 |
O3—N4—C8 | 117.2 (3) | H14A—C14—H14C | 109.5 |
O4—N4—C8 | 118.1 (4) | H14B—C14—H14C | 109.5 |
C17—N5—N5i | 114.4 (3) | N2—C15—C16 | 112.7 (4) |
C17—N5—C23 | 120.9 (3) | N2—C15—H15A | 109.1 |
N5i—N5—C23 | 119.1 (2) | C16—C15—H15A | 109.1 |
O5—N6—O6 | 124.5 (4) | N2—C15—H15B | 109.1 |
O5—N6—C18 | 118.5 (4) | C16—C15—H15B | 109.1 |
O6—N6—C18 | 117.0 (4) | H15A—C15—H15B | 107.8 |
N1—C1—C2 | 123.8 (4) | C15—C16—H16A | 109.5 |
N1—C1—C6 | 121.5 (4) | C15—C16—H16B | 109.5 |
C2—C1—C6 | 114.8 (4) | H16A—C16—H16B | 109.5 |
C3—C2—C1 | 123.5 (5) | C15—C16—H16C | 109.5 |
C3—C2—N3 | 114.4 (5) | H16A—C16—H16C | 109.5 |
C1—C2—N3 | 122.0 (4) | H16B—C16—H16C | 109.5 |
C4—C3—C2 | 119.9 (5) | C19—C18—C17 | 122.7 (4) |
C4—C3—H3 | 120.0 | C19—C18—N6 | 114.4 (4) |
C2—C3—H3 | 120.0 | C17—C18—N6 | 122.7 (4) |
C5—C4—C3 | 118.7 (5) | C18—C17—N5 | 124.2 (4) |
C5—C4—H4 | 120.6 | C18—C17—C22 | 115.3 (4) |
C3—C4—H4 | 120.6 | N5—C17—C22 | 120.4 (4) |
C4—C5—C6 | 121.3 (5) | C21—C22—C17 | 121.7 (4) |
C4—C5—H5 | 119.4 | C21—C22—H22 | 119.1 |
C6—C5—H5 | 119.4 | C17—C22—H22 | 119.1 |
C5—C6—C1 | 121.7 (5) | C22—C21—C20 | 121.3 (5) |
C5—C6—H6 | 119.2 | C22—C21—H21 | 119.4 |
C1—C6—H6 | 119.2 | C20—C21—H21 | 119.4 |
C8—C7—C12 | 115.2 (4) | C19—C20—C21 | 118.0 (5) |
C8—C7—N2 | 123.0 (4) | C19—C20—H20 | 121.0 |
C12—C7—N2 | 121.8 (4) | C21—C20—H20 | 121.0 |
C9—C8—C7 | 123.5 (4) | C20—C19—C18 | 120.7 (5) |
C9—C8—N4 | 114.3 (4) | C20—C19—H19 | 119.6 |
C7—C8—N4 | 122.2 (4) | C18—C19—H19 | 119.6 |
C8—C9—C10 | 119.3 (4) | C24—C23—N5 | 110.9 (5) |
C8—C9—H9 | 120.3 | C24—C23—H23A | 109.5 |
C10—C9—H9 | 120.3 | N5—C23—H23A | 109.5 |
C11—C10—C9 | 118.9 (5) | C24—C23—H23B | 109.5 |
C11—C10—H10 | 120.6 | N5—C23—H23B | 109.5 |
C9—C10—H10 | 120.6 | H23A—C23—H23B | 108.1 |
C12—C11—C10 | 121.1 (5) | C23—C24—H24A | 109.5 |
C12—C11—H11 | 119.4 | C23—C24—H24B | 109.5 |
C10—C11—H11 | 119.4 | H24A—C24—H24B | 109.5 |
C11—C12—C7 | 121.9 (4) | C23—C24—H24C | 109.5 |
C11—C12—H12 | 119.1 | H24A—C24—H24C | 109.5 |
C7—C12—H12 | 119.1 | H24B—C24—H24C | 109.5 |
| | | |
C1—N1—N2—C7 | −134.4 (4) | O4—N4—C8—C7 | 135.8 (4) |
C13—N1—N2—C7 | 80.3 (4) | C7—C8—C9—C10 | 2.5 (7) |
C1—N1—N2—C15 | 88.7 (4) | N4—C8—C9—C10 | −174.7 (4) |
C13—N1—N2—C15 | −56.7 (5) | C8—C9—C10—C11 | 1.2 (7) |
N2—N1—C1—C2 | 39.3 (5) | C9—C10—C11—C12 | −2.9 (7) |
C13—N1—C1—C2 | −176.0 (4) | C10—C11—C12—C7 | 1.0 (7) |
N2—N1—C1—C6 | −140.1 (4) | C8—C7—C12—C11 | 2.4 (6) |
C13—N1—C1—C6 | 4.6 (6) | N2—C7—C12—C11 | −177.7 (4) |
N1—C1—C2—C3 | −177.5 (4) | C1—N1—C13—C14 | 72.6 (5) |
C6—C1—C2—C3 | 2.0 (7) | N2—N1—C13—C14 | −143.5 (4) |
N1—C1—C2—N3 | 5.8 (7) | C7—N2—C15—C16 | 147.1 (4) |
C6—C1—C2—N3 | −174.7 (4) | N1—N2—C15—C16 | −78.4 (5) |
O1—N3—C2—C3 | 47.8 (6) | O5—N6—C18—C19 | 135.0 (5) |
O2—N3—C2—C3 | −128.5 (5) | O6—N6—C18—C19 | −42.0 (7) |
O1—N3—C2—C1 | −135.2 (5) | O5—N6—C18—C17 | −41.3 (7) |
O2—N3—C2—C1 | 48.5 (6) | O6—N6—C18—C17 | 141.8 (5) |
C1—C2—C3—C4 | −3.3 (7) | C19—C18—C17—N5 | 178.5 (4) |
N3—C2—C3—C4 | 173.6 (5) | N6—C18—C17—N5 | −5.6 (7) |
C2—C3—C4—C5 | 2.1 (8) | C19—C18—C17—C22 | −4.6 (6) |
C3—C4—C5—C6 | 0.2 (8) | N6—C18—C17—C22 | 171.4 (4) |
C4—C5—C6—C1 | −1.4 (8) | N5i—N5—C17—C18 | 157.5 (4) |
N1—C1—C6—C5 | 179.8 (4) | C23—N5—C17—C18 | −48.9 (6) |
C2—C1—C6—C5 | 0.4 (7) | N5i—N5—C17—C22 | −19.3 (6) |
N1—N2—C7—C8 | 178.2 (4) | C23—N5—C17—C22 | 134.3 (5) |
C15—N2—C7—C8 | −47.5 (6) | C18—C17—C22—C21 | 3.1 (6) |
N1—N2—C7—C12 | −1.7 (5) | N5—C17—C22—C21 | −179.8 (4) |
C15—N2—C7—C12 | 132.6 (4) | C17—C22—C21—C20 | −0.6 (7) |
C12—C7—C8—C9 | −4.2 (6) | C22—C21—C20—C19 | −0.6 (7) |
N2—C7—C8—C9 | 175.9 (4) | C21—C20—C19—C18 | −0.8 (7) |
C12—C7—C8—N4 | 172.8 (4) | C17—C18—C19—C20 | 3.6 (7) |
N2—C7—C8—N4 | −7.1 (6) | N6—C18—C19—C20 | −172.6 (5) |
O3—N4—C8—C9 | 131.6 (5) | C17—N5—C23—C24 | 143.3 (5) |
O4—N4—C8—C9 | −46.9 (6) | N5i—N5—C23—C24 | −64.3 (6) |
O3—N4—C8—C7 | −45.6 (7) | | |
Symmetry code: (i) −x+1, −y, z. |