organic compounds
(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-nitrophenyl)ethylidene]hydrazine
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my
In the 14H11N5O6, there are three crystallographically independent molecules with similar conformations but some differences in bond angles. The molecules are slightly twisted with the dihedral angles between the benzene rings being 10.02 (14), 8.41 (15) and 1.40 (14)°. In each molecule, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by weak C—H⋯O interactions into a three-dimensional network. π–π interactions with centroid–centroid distances of 3.5635 (17)–3.8273 (18) Å are observed.
of the title compound, CRelated literature
For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For a related structure, see: Chantrapromma et al. (2011). For background to and the biological activity of hydrozones, see: Cui et al. (2010); Krishnamoorthy et al. (2011); Molyneux (2004); Raja et al. (2012); Sathyadevi et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812034812/is5180sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034812/is5180Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034812/is5180Isup3.cml
The title compound (I) was synthesized by dissolving 2,4-dinitrophenylhydrazine (0.40 g, 2 mmol) in ethanol (10.00 ml) and H2SO4 (conc.) (98%, 0.50 ml) was slowly added with stirring. 3-Nitroacetophenone (0.35 g, 2 mmol) in ethanol (10.00 ml) was then added to the solution with continuous stirring. The solution was refluxed for 1 hr yielding an yellow solid which was filtered off and washed with methanol. Yellow block-shaped single crystals of the title compound suitable for X-ray
were recrystalized from ethanol by slow evaporation of the solvent at room temperature over several days (m.p. 507–508 K).All H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H = 0.88 Å, C—H = 0.95 Å for aromatic and 0.98 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the
for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The asymmetric unit of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bond is shown as a dashed line. | |
Fig. 2. The crystal packing diagram of the title compound viewed approximately along the c axis. Hydrogen bonds are shown as dashed lines. |
C14H11N5O6 | F(000) = 2136 |
Mr = 345.28 | Dx = 1.609 Mg m−3 |
Monoclinic, P21/c | Melting point = 507–508 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3309 (2) Å | Cell parameters from 12460 reflections |
b = 38.3569 (8) Å | θ = 1.1–30.0° |
c = 16.8027 (4) Å | µ = 0.13 mm−1 |
β = 115.158 (1)° | T = 100 K |
V = 4276.57 (18) Å3 | Block, yellow |
Z = 12 | 0.49 × 0.10 × 0.10 mm |
Bruker APEXII CCD area-detector diffractometer | 12460 independent reflections |
Radiation source: sealed tube | 7719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ϕ and ω scans | θmax = 30.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→10 |
Tmin = 0.940, Tmax = 0.988 | k = −49→53 |
49752 measured reflections | l = −22→23 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0437P)2 + 3.8937P] where P = (Fo2 + 2Fc2)/3 |
12460 reflections | (Δ/σ)max = 0.001 |
679 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C14H11N5O6 | V = 4276.57 (18) Å3 |
Mr = 345.28 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.3309 (2) Å | µ = 0.13 mm−1 |
b = 38.3569 (8) Å | T = 100 K |
c = 16.8027 (4) Å | 0.49 × 0.10 × 0.10 mm |
β = 115.158 (1)° |
Bruker APEXII CCD area-detector diffractometer | 12460 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 7719 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.988 | Rint = 0.072 |
49752 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.51 e Å−3 |
12460 reflections | Δρmin = −0.38 e Å−3 |
679 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K. |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 1.0005 (3) | 0.92844 (5) | 0.64127 (11) | 0.0268 (4) | |
O2A | 0.9875 (3) | 0.97771 (5) | 0.57674 (12) | 0.0276 (4) | |
O3A | 0.6139 (3) | 0.99217 (5) | 0.26790 (13) | 0.0359 (5) | |
O4A | 0.3472 (3) | 0.95996 (5) | 0.20354 (11) | 0.0254 (4) | |
O5A | 0.2251 (3) | 0.75669 (5) | 0.35614 (12) | 0.0261 (4) | |
O6A | 0.2531 (4) | 0.70272 (5) | 0.39490 (14) | 0.0472 (6) | |
N1A | 0.7915 (3) | 0.87484 (5) | 0.55324 (13) | 0.0172 (4) | |
H1AA | 0.8764 | 0.8817 | 0.6060 | 0.021* | |
N2A | 0.7233 (3) | 0.84100 (5) | 0.53897 (13) | 0.0171 (4) | |
N3A | 0.9363 (3) | 0.94709 (5) | 0.57465 (13) | 0.0177 (4) | |
N4A | 0.5092 (3) | 0.96680 (6) | 0.26601 (14) | 0.0209 (5) | |
N5A | 0.3093 (3) | 0.73305 (6) | 0.40790 (14) | 0.0241 (5) | |
C1A | 0.7255 (4) | 0.89752 (6) | 0.48449 (15) | 0.0151 (5) | |
C2A | 0.7932 (3) | 0.93258 (6) | 0.49190 (15) | 0.0150 (5) | |
C3A | 0.7244 (4) | 0.95503 (6) | 0.41999 (16) | 0.0167 (5) | |
H3AA | 0.7756 | 0.9781 | 0.4254 | 0.020* | |
C4A | 0.5813 (4) | 0.94319 (6) | 0.34122 (15) | 0.0169 (5) | |
C5A | 0.5038 (4) | 0.90923 (6) | 0.33111 (16) | 0.0175 (5) | |
H5AA | 0.4012 | 0.9019 | 0.2764 | 0.021* | |
C6A | 0.5780 (4) | 0.88679 (6) | 0.40110 (15) | 0.0175 (5) | |
H6AA | 0.5296 | 0.8635 | 0.3936 | 0.021* | |
C7A | 0.7690 (4) | 0.82152 (6) | 0.60742 (15) | 0.0163 (5) | |
C8A | 0.6995 (4) | 0.78476 (6) | 0.58883 (15) | 0.0160 (5) | |
C9A | 0.5443 (4) | 0.77613 (6) | 0.50711 (15) | 0.0170 (5) | |
H9AA | 0.4835 | 0.7934 | 0.4633 | 0.020* | |
C10A | 0.4817 (4) | 0.74167 (6) | 0.49183 (16) | 0.0193 (5) | |
C11A | 0.5691 (4) | 0.71538 (6) | 0.55242 (17) | 0.0220 (5) | |
H11A | 0.5253 | 0.6919 | 0.5391 | 0.026* | |
C12A | 0.7215 (4) | 0.72408 (7) | 0.63267 (17) | 0.0219 (5) | |
H12A | 0.7839 | 0.7065 | 0.6754 | 0.026* | |
C13A | 0.7846 (4) | 0.75853 (6) | 0.65159 (16) | 0.0189 (5) | |
H13A | 0.8868 | 0.7643 | 0.7079 | 0.023* | |
C14A | 0.8828 (4) | 0.83316 (7) | 0.70094 (17) | 0.0272 (6) | |
H14A | 0.8557 | 0.8579 | 0.7058 | 0.041* | |
H14B | 1.0276 | 0.8298 | 0.7191 | 0.041* | |
H14C | 0.8396 | 0.8194 | 0.7390 | 0.041* | |
O1B | 1.0090 (3) | 0.91068 (5) | 1.14668 (12) | 0.0260 (4) | |
O2B | 0.8666 (3) | 0.86026 (4) | 1.10339 (12) | 0.0266 (4) | |
O3B | 0.4725 (4) | 0.83754 (6) | 0.80216 (16) | 0.0654 (9) | |
O4B | 0.2945 (3) | 0.87838 (5) | 0.71768 (12) | 0.0334 (5) | |
O5B | 0.3878 (3) | 1.09140 (5) | 0.83376 (11) | 0.0236 (4) | |
O6B | 0.5168 (3) | 1.14326 (5) | 0.84719 (12) | 0.0309 (5) | |
N1B | 0.8365 (3) | 0.96614 (5) | 1.05174 (13) | 0.0190 (4) | |
H1BA | 0.9170 | 0.9595 | 1.1054 | 0.023* | |
N2B | 0.8059 (3) | 1.00095 (5) | 1.03058 (13) | 0.0191 (4) | |
N3B | 0.8860 (3) | 0.89130 (5) | 1.09028 (14) | 0.0198 (4) | |
N4B | 0.4247 (3) | 0.86807 (6) | 0.78739 (15) | 0.0265 (5) | |
N5B | 0.5170 (3) | 1.11357 (6) | 0.87446 (14) | 0.0212 (5) | |
C1B | 0.7396 (4) | 0.94219 (6) | 0.98780 (16) | 0.0178 (5) | |
C2B | 0.7587 (4) | 0.90569 (6) | 1.00424 (15) | 0.0167 (5) | |
C3B | 0.6541 (4) | 0.88183 (6) | 0.93861 (16) | 0.0190 (5) | |
H3BA | 0.6687 | 0.8575 | 0.9506 | 0.023* | |
C4B | 0.5301 (4) | 0.89357 (6) | 0.85670 (16) | 0.0192 (5) | |
C5B | 0.5034 (4) | 0.92931 (7) | 0.83717 (16) | 0.0193 (5) | |
H5BA | 0.4142 | 0.9370 | 0.7800 | 0.023* | |
C6B | 0.6080 (4) | 0.95299 (6) | 0.90184 (15) | 0.0187 (5) | |
H6BA | 0.5918 | 0.9772 | 0.8886 | 0.022* | |
C7B | 0.8768 (4) | 1.02291 (6) | 1.09502 (16) | 0.0168 (5) | |
C8B | 0.8458 (4) | 1.06007 (6) | 1.06806 (15) | 0.0164 (5) | |
C9B | 0.6992 (4) | 1.06913 (6) | 0.98502 (15) | 0.0170 (5) | |
H9BA | 0.6163 | 1.0518 | 0.9459 | 0.020* | |
C10B | 0.6771 (4) | 1.10396 (6) | 0.96097 (15) | 0.0168 (5) | |
C11B | 0.7940 (4) | 1.13023 (6) | 1.01474 (16) | 0.0195 (5) | |
H11B | 0.7764 | 1.1538 | 0.9957 | 0.023* | |
C12B | 0.9374 (4) | 1.12102 (6) | 1.09710 (16) | 0.0199 (5) | |
H12B | 1.0197 | 1.1385 | 1.1356 | 0.024* | |
C13B | 0.9629 (4) | 1.08631 (6) | 1.12452 (16) | 0.0187 (5) | |
H13B | 1.0602 | 1.0805 | 1.1818 | 0.022* | |
C14B | 0.9801 (4) | 1.01340 (7) | 1.19055 (16) | 0.0264 (6) | |
H14D | 0.9211 | 0.9919 | 1.2008 | 0.040* | |
H14E | 0.9627 | 1.0323 | 1.2260 | 0.040* | |
H14F | 1.1241 | 1.0098 | 1.2072 | 0.040* | |
O1C | −0.1689 (3) | 0.74191 (5) | 0.38978 (12) | 0.0275 (4) | |
O2C | −0.1244 (3) | 0.69066 (5) | 0.44882 (12) | 0.0296 (5) | |
O3C | 0.2722 (3) | 0.67220 (5) | 0.75401 (12) | 0.0282 (4) | |
O4C | 0.5339 (3) | 0.70556 (5) | 0.81641 (12) | 0.0257 (4) | |
O5C | 0.5986 (3) | 0.91628 (5) | 0.66988 (12) | 0.0294 (4) | |
O6C | 0.5778 (3) | 0.96939 (5) | 0.62208 (14) | 0.0362 (5) | |
N1C | 0.0454 (3) | 0.79484 (5) | 0.47944 (13) | 0.0174 (4) | |
H1CA | −0.0484 | 0.7885 | 0.4280 | 0.021* | |
N2C | 0.1181 (3) | 0.82847 (5) | 0.49206 (13) | 0.0170 (4) | |
N3C | −0.0874 (3) | 0.72206 (5) | 0.45348 (14) | 0.0199 (4) | |
N4C | 0.3685 (3) | 0.69869 (5) | 0.75661 (13) | 0.0192 (4) | |
N5C | 0.5215 (3) | 0.93881 (6) | 0.61320 (14) | 0.0225 (5) | |
C1C | 0.1188 (4) | 0.77154 (6) | 0.54654 (16) | 0.0163 (5) | |
C2C | 0.0576 (4) | 0.73607 (6) | 0.53636 (15) | 0.0168 (5) | |
C3C | 0.1358 (4) | 0.71267 (6) | 0.60596 (16) | 0.0175 (5) | |
H3CA | 0.0887 | 0.6893 | 0.5990 | 0.021* | |
C4C | 0.2817 (4) | 0.72381 (6) | 0.68475 (16) | 0.0177 (5) | |
C5C | 0.3507 (4) | 0.75844 (6) | 0.69789 (16) | 0.0183 (5) | |
H5CA | 0.4538 | 0.7655 | 0.7528 | 0.022* | |
C6C | 0.2673 (4) | 0.78189 (6) | 0.63043 (16) | 0.0186 (5) | |
H6CA | 0.3094 | 0.8055 | 0.6399 | 0.022* | |
C7C | 0.0635 (4) | 0.84757 (6) | 0.42229 (16) | 0.0155 (5) | |
C8C | 0.1381 (3) | 0.88409 (6) | 0.43691 (15) | 0.0159 (5) | |
C9C | 0.2878 (3) | 0.89426 (6) | 0.51852 (15) | 0.0166 (5) | |
H9CA | 0.3415 | 0.8782 | 0.5658 | 0.020* | |
C10C | 0.3557 (4) | 0.92842 (7) | 0.52864 (16) | 0.0188 (5) | |
C11C | 0.2798 (4) | 0.95319 (7) | 0.46272 (17) | 0.0213 (5) | |
H11C | 0.3289 | 0.9765 | 0.4722 | 0.026* | |
C12C | 0.1305 (4) | 0.94299 (7) | 0.38283 (17) | 0.0224 (5) | |
H12C | 0.0747 | 0.9595 | 0.3366 | 0.027* | |
C13C | 0.0606 (4) | 0.90885 (6) | 0.36922 (16) | 0.0184 (5) | |
H13C | −0.0407 | 0.9022 | 0.3135 | 0.022* | |
C14C | −0.0651 (4) | 0.83538 (7) | 0.33029 (16) | 0.0213 (5) | |
H14G | −0.0393 | 0.8106 | 0.3251 | 0.032* | |
H14H | −0.0323 | 0.8489 | 0.2886 | 0.032* | |
H14J | −0.2076 | 0.8387 | 0.3172 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0358 (11) | 0.0155 (9) | 0.0182 (9) | −0.0019 (8) | 0.0009 (9) | 0.0017 (7) |
O2A | 0.0367 (11) | 0.0116 (9) | 0.0281 (10) | −0.0104 (8) | 0.0075 (9) | −0.0028 (8) |
O3A | 0.0391 (12) | 0.0254 (11) | 0.0337 (11) | −0.0106 (9) | 0.0063 (10) | 0.0128 (9) |
O4A | 0.0245 (10) | 0.0247 (10) | 0.0195 (9) | 0.0024 (8) | 0.0022 (8) | 0.0006 (8) |
O5A | 0.0274 (10) | 0.0230 (10) | 0.0221 (9) | −0.0029 (8) | 0.0048 (8) | 0.0017 (8) |
O6A | 0.0701 (17) | 0.0199 (11) | 0.0339 (12) | −0.0224 (11) | 0.0051 (12) | −0.0043 (9) |
N1A | 0.0234 (11) | 0.0084 (10) | 0.0156 (10) | −0.0035 (8) | 0.0041 (9) | −0.0013 (8) |
N2A | 0.0208 (11) | 0.0089 (10) | 0.0200 (10) | −0.0020 (8) | 0.0072 (9) | −0.0017 (8) |
N3A | 0.0182 (10) | 0.0132 (11) | 0.0187 (10) | −0.0030 (8) | 0.0051 (9) | −0.0032 (8) |
N4A | 0.0231 (11) | 0.0165 (11) | 0.0199 (11) | 0.0023 (9) | 0.0062 (10) | 0.0015 (9) |
N5A | 0.0299 (13) | 0.0203 (12) | 0.0221 (11) | −0.0089 (10) | 0.0111 (10) | −0.0029 (9) |
C1A | 0.0174 (12) | 0.0113 (11) | 0.0168 (11) | 0.0008 (9) | 0.0074 (10) | −0.0015 (9) |
C2A | 0.0149 (11) | 0.0123 (12) | 0.0156 (11) | −0.0025 (9) | 0.0044 (10) | −0.0023 (9) |
C3A | 0.0190 (12) | 0.0093 (11) | 0.0226 (12) | −0.0013 (9) | 0.0094 (11) | −0.0002 (9) |
C4A | 0.0187 (12) | 0.0148 (12) | 0.0176 (11) | 0.0028 (9) | 0.0081 (10) | 0.0034 (9) |
C5A | 0.0172 (12) | 0.0167 (13) | 0.0181 (12) | −0.0025 (10) | 0.0070 (10) | −0.0031 (9) |
C6A | 0.0190 (12) | 0.0130 (12) | 0.0196 (12) | −0.0033 (9) | 0.0075 (10) | −0.0045 (9) |
C7A | 0.0178 (12) | 0.0122 (12) | 0.0178 (11) | −0.0015 (9) | 0.0063 (10) | −0.0006 (9) |
C8A | 0.0184 (12) | 0.0119 (12) | 0.0185 (12) | 0.0003 (9) | 0.0086 (10) | 0.0009 (9) |
C9A | 0.0212 (12) | 0.0123 (12) | 0.0174 (11) | −0.0008 (9) | 0.0082 (10) | −0.0003 (9) |
C10A | 0.0226 (13) | 0.0166 (13) | 0.0190 (12) | −0.0051 (10) | 0.0093 (11) | −0.0041 (10) |
C11A | 0.0289 (14) | 0.0109 (12) | 0.0270 (14) | −0.0014 (10) | 0.0128 (12) | 0.0016 (10) |
C12A | 0.0244 (13) | 0.0147 (13) | 0.0249 (13) | 0.0023 (10) | 0.0088 (12) | 0.0080 (10) |
C13A | 0.0181 (12) | 0.0168 (13) | 0.0194 (12) | 0.0001 (10) | 0.0056 (10) | 0.0015 (10) |
C14A | 0.0379 (16) | 0.0167 (14) | 0.0196 (13) | −0.0032 (12) | 0.0052 (12) | −0.0002 (10) |
O1B | 0.0257 (10) | 0.0190 (10) | 0.0227 (9) | −0.0029 (8) | 0.0000 (8) | 0.0006 (8) |
O2B | 0.0398 (12) | 0.0102 (9) | 0.0266 (10) | 0.0045 (8) | 0.0110 (9) | 0.0042 (7) |
O3B | 0.0775 (19) | 0.0186 (12) | 0.0493 (15) | 0.0105 (12) | −0.0220 (14) | −0.0143 (11) |
O4B | 0.0345 (12) | 0.0299 (12) | 0.0223 (10) | −0.0046 (9) | −0.0010 (9) | −0.0023 (8) |
O5B | 0.0237 (10) | 0.0202 (10) | 0.0220 (9) | 0.0008 (8) | 0.0050 (8) | −0.0036 (8) |
O6B | 0.0378 (12) | 0.0190 (10) | 0.0285 (10) | 0.0022 (9) | 0.0070 (9) | 0.0090 (8) |
N1B | 0.0247 (11) | 0.0118 (10) | 0.0159 (10) | −0.0002 (8) | 0.0042 (9) | 0.0012 (8) |
N2B | 0.0228 (11) | 0.0123 (10) | 0.0199 (10) | 0.0007 (8) | 0.0070 (9) | 0.0012 (8) |
N3B | 0.0234 (11) | 0.0143 (11) | 0.0212 (11) | 0.0017 (9) | 0.0090 (10) | 0.0008 (8) |
N4B | 0.0267 (12) | 0.0207 (13) | 0.0248 (12) | −0.0014 (10) | 0.0039 (10) | −0.0042 (9) |
N5B | 0.0248 (11) | 0.0169 (11) | 0.0202 (11) | 0.0031 (9) | 0.0078 (10) | −0.0008 (9) |
C1B | 0.0202 (12) | 0.0146 (12) | 0.0194 (12) | −0.0002 (10) | 0.0092 (10) | −0.0001 (10) |
C2B | 0.0179 (12) | 0.0140 (12) | 0.0175 (11) | 0.0010 (9) | 0.0068 (10) | 0.0008 (9) |
C3B | 0.0201 (13) | 0.0119 (12) | 0.0236 (13) | −0.0002 (10) | 0.0079 (11) | −0.0020 (10) |
C4B | 0.0185 (12) | 0.0169 (13) | 0.0204 (12) | −0.0024 (10) | 0.0063 (11) | −0.0058 (10) |
C5B | 0.0193 (12) | 0.0209 (13) | 0.0169 (12) | 0.0023 (10) | 0.0069 (10) | 0.0022 (10) |
C6B | 0.0217 (13) | 0.0153 (13) | 0.0178 (12) | 0.0034 (10) | 0.0071 (11) | 0.0026 (9) |
C7B | 0.0205 (12) | 0.0113 (12) | 0.0181 (12) | 0.0010 (9) | 0.0076 (10) | 0.0001 (9) |
C8B | 0.0191 (12) | 0.0130 (12) | 0.0165 (11) | −0.0008 (9) | 0.0071 (10) | −0.0017 (9) |
C9B | 0.0177 (12) | 0.0154 (12) | 0.0172 (11) | −0.0006 (9) | 0.0068 (10) | −0.0022 (9) |
C10B | 0.0186 (12) | 0.0155 (12) | 0.0149 (11) | 0.0038 (9) | 0.0057 (10) | 0.0025 (9) |
C11B | 0.0247 (13) | 0.0114 (12) | 0.0228 (13) | 0.0010 (10) | 0.0103 (11) | 0.0001 (10) |
C12B | 0.0235 (13) | 0.0139 (12) | 0.0207 (12) | −0.0048 (10) | 0.0079 (11) | −0.0062 (10) |
C13B | 0.0194 (12) | 0.0169 (13) | 0.0169 (11) | −0.0005 (10) | 0.0050 (10) | −0.0020 (9) |
C14B | 0.0379 (16) | 0.0157 (13) | 0.0198 (13) | 0.0033 (12) | 0.0067 (12) | −0.0006 (10) |
O1C | 0.0319 (11) | 0.0156 (10) | 0.0234 (10) | −0.0011 (8) | 0.0004 (9) | 0.0041 (8) |
O2C | 0.0362 (11) | 0.0106 (9) | 0.0299 (10) | −0.0063 (8) | 0.0024 (9) | −0.0026 (8) |
O3C | 0.0300 (11) | 0.0185 (10) | 0.0316 (11) | −0.0023 (8) | 0.0088 (9) | 0.0074 (8) |
O4C | 0.0213 (10) | 0.0264 (11) | 0.0211 (9) | 0.0031 (8) | 0.0010 (8) | 0.0028 (8) |
O5C | 0.0267 (10) | 0.0303 (11) | 0.0234 (10) | −0.0038 (9) | 0.0032 (9) | −0.0006 (8) |
O6C | 0.0383 (12) | 0.0194 (11) | 0.0402 (12) | −0.0093 (9) | 0.0064 (10) | −0.0093 (9) |
N1C | 0.0215 (11) | 0.0100 (10) | 0.0162 (10) | −0.0016 (8) | 0.0035 (9) | −0.0005 (8) |
N2C | 0.0199 (11) | 0.0096 (10) | 0.0212 (10) | −0.0013 (8) | 0.0084 (9) | −0.0019 (8) |
N3C | 0.0195 (11) | 0.0153 (11) | 0.0211 (11) | −0.0016 (9) | 0.0050 (9) | −0.0014 (9) |
N4C | 0.0214 (11) | 0.0160 (11) | 0.0179 (10) | 0.0026 (9) | 0.0061 (9) | 0.0019 (8) |
N5C | 0.0213 (11) | 0.0214 (12) | 0.0235 (11) | −0.0028 (9) | 0.0084 (10) | −0.0058 (9) |
C1C | 0.0197 (12) | 0.0114 (12) | 0.0190 (12) | 0.0000 (9) | 0.0096 (10) | −0.0004 (9) |
C2C | 0.0188 (12) | 0.0109 (12) | 0.0170 (11) | −0.0006 (9) | 0.0041 (10) | −0.0007 (9) |
C3C | 0.0203 (12) | 0.0099 (12) | 0.0222 (12) | −0.0004 (9) | 0.0090 (11) | −0.0013 (9) |
C4C | 0.0185 (12) | 0.0155 (12) | 0.0185 (12) | 0.0026 (10) | 0.0073 (10) | 0.0039 (9) |
C5C | 0.0201 (12) | 0.0158 (13) | 0.0178 (12) | −0.0025 (10) | 0.0068 (10) | −0.0012 (9) |
C6C | 0.0227 (13) | 0.0128 (12) | 0.0197 (12) | −0.0041 (10) | 0.0084 (11) | −0.0022 (9) |
C7C | 0.0156 (11) | 0.0097 (11) | 0.0197 (12) | −0.0006 (9) | 0.0061 (10) | −0.0005 (9) |
C8C | 0.0163 (12) | 0.0143 (12) | 0.0176 (11) | 0.0007 (9) | 0.0078 (10) | 0.0007 (9) |
C9C | 0.0170 (12) | 0.0139 (12) | 0.0165 (11) | 0.0021 (9) | 0.0048 (10) | 0.0011 (9) |
C10C | 0.0157 (12) | 0.0184 (13) | 0.0208 (12) | −0.0013 (10) | 0.0063 (10) | −0.0045 (10) |
C11C | 0.0231 (13) | 0.0113 (12) | 0.0317 (14) | −0.0014 (10) | 0.0137 (12) | −0.0002 (10) |
C12C | 0.0244 (13) | 0.0183 (13) | 0.0239 (13) | 0.0039 (11) | 0.0097 (11) | 0.0073 (10) |
C13C | 0.0186 (12) | 0.0163 (13) | 0.0184 (12) | 0.0005 (10) | 0.0061 (10) | 0.0007 (10) |
C14C | 0.0243 (13) | 0.0148 (13) | 0.0183 (12) | −0.0034 (10) | 0.0027 (11) | −0.0001 (10) |
O1A—N3A | 1.240 (3) | C5B—C6B | 1.373 (3) |
O2A—N3A | 1.229 (3) | C5B—H5BA | 0.9500 |
O3A—N4A | 1.231 (3) | C6B—H6BA | 0.9500 |
O4A—N4A | 1.234 (3) | C7B—C8B | 1.483 (3) |
O5A—N5A | 1.226 (3) | C7B—C14B | 1.500 (3) |
O6A—N5A | 1.222 (3) | C8B—C9B | 1.396 (3) |
N1A—C1A | 1.360 (3) | C8B—C13B | 1.399 (3) |
N1A—N2A | 1.375 (3) | C9B—C10B | 1.385 (3) |
N1A—H1AA | 0.8800 | C9B—H9BA | 0.9500 |
N2A—C7A | 1.291 (3) | C10B—C11B | 1.381 (3) |
N3A—C2A | 1.450 (3) | C11B—C12B | 1.381 (4) |
N4A—C4A | 1.459 (3) | C11B—H11B | 0.9500 |
N5A—C10A | 1.476 (3) | C12B—C13B | 1.395 (3) |
C1A—C6A | 1.419 (3) | C12B—H12B | 0.9500 |
C1A—C2A | 1.420 (3) | C13B—H13B | 0.9500 |
C2A—C3A | 1.392 (3) | C14B—H14D | 0.9800 |
C3A—C4A | 1.370 (3) | C14B—H14E | 0.9800 |
C3A—H3AA | 0.9500 | C14B—H14F | 0.9800 |
C4A—C5A | 1.402 (3) | O1C—N3C | 1.240 (3) |
C5A—C6A | 1.370 (3) | O2C—N3C | 1.230 (3) |
C5A—H5AA | 0.9500 | O3C—N4C | 1.228 (3) |
C6A—H6AA | 0.9500 | O4C—N4C | 1.230 (3) |
C7A—C8A | 1.486 (3) | O5C—N5C | 1.231 (3) |
C7A—C14A | 1.500 (3) | O6C—N5C | 1.231 (3) |
C8A—C13A | 1.398 (3) | N1C—C1C | 1.358 (3) |
C8A—C9A | 1.400 (3) | N1C—N2C | 1.377 (3) |
C9A—C10A | 1.387 (3) | N1C—H1CA | 0.8800 |
C9A—H9AA | 0.9500 | N2C—C7C | 1.293 (3) |
C10A—C11A | 1.382 (3) | N3C—C2C | 1.449 (3) |
C11A—C12A | 1.377 (4) | N4C—C4C | 1.462 (3) |
C11A—H11A | 0.9500 | N5C—C10C | 1.479 (3) |
C12A—C13A | 1.391 (3) | C1C—C2C | 1.420 (3) |
C12A—H12A | 0.9500 | C1C—C6C | 1.423 (3) |
C13A—H13A | 0.9500 | C2C—C3C | 1.390 (3) |
C14A—H14A | 0.9800 | C3C—C4C | 1.369 (3) |
C14A—H14B | 0.9800 | C3C—H3CA | 0.9500 |
C14A—H14C | 0.9800 | C4C—C5C | 1.405 (3) |
O1B—N3B | 1.240 (3) | C5C—C6C | 1.370 (3) |
O2B—N3B | 1.230 (3) | C5C—H5CA | 0.9500 |
O3B—N4B | 1.217 (3) | C6C—H6CA | 0.9500 |
O4B—N4B | 1.220 (3) | C7C—C8C | 1.486 (3) |
O5B—N5B | 1.239 (3) | C7C—C14C | 1.503 (3) |
O6B—N5B | 1.227 (3) | C8C—C9C | 1.399 (3) |
N1B—C1B | 1.362 (3) | C8C—C13C | 1.403 (3) |
N1B—N2B | 1.375 (3) | C9C—C10C | 1.386 (3) |
N1B—H1BA | 0.8800 | C9C—H9CA | 0.9500 |
N2B—C7B | 1.294 (3) | C10C—C11C | 1.384 (4) |
N3B—C2B | 1.456 (3) | C11C—C12C | 1.380 (4) |
N4B—C4B | 1.464 (3) | C11C—H11C | 0.9500 |
N5B—C10B | 1.475 (3) | C12C—C13C | 1.389 (3) |
C1B—C6B | 1.415 (3) | C12C—H12C | 0.9500 |
C1B—C2B | 1.423 (3) | C13C—H13C | 0.9500 |
C2B—C3B | 1.386 (3) | C14C—H14G | 0.9800 |
C3B—C4B | 1.364 (3) | C14C—H14H | 0.9800 |
C3B—H3BA | 0.9500 | C14C—H14J | 0.9800 |
C4B—C5B | 1.404 (3) | ||
C1A—N1A—N2A | 118.9 (2) | C5B—C6B—H6BA | 119.2 |
C1A—N1A—H1AA | 120.5 | C1B—C6B—H6BA | 119.2 |
N2A—N1A—H1AA | 120.5 | N2B—C7B—C8B | 114.5 (2) |
C7A—N2A—N1A | 117.0 (2) | N2B—C7B—C14B | 125.3 (2) |
O2A—N3A—O1A | 122.1 (2) | C8B—C7B—C14B | 120.2 (2) |
O2A—N3A—C2A | 118.8 (2) | C9B—C8B—C13B | 119.2 (2) |
O1A—N3A—C2A | 119.1 (2) | C9B—C8B—C7B | 119.8 (2) |
O3A—N4A—O4A | 123.7 (2) | C13B—C8B—C7B | 120.9 (2) |
O3A—N4A—C4A | 118.4 (2) | C10B—C9B—C8B | 118.5 (2) |
O4A—N4A—C4A | 117.9 (2) | C10B—C9B—H9BA | 120.8 |
O6A—N5A—O5A | 123.2 (2) | C8B—C9B—H9BA | 120.8 |
O6A—N5A—C10A | 118.1 (2) | C11B—C10B—C9B | 123.4 (2) |
O5A—N5A—C10A | 118.7 (2) | C11B—C10B—N5B | 118.3 (2) |
N1A—C1A—C6A | 120.0 (2) | C9B—C10B—N5B | 118.3 (2) |
N1A—C1A—C2A | 123.1 (2) | C10B—C11B—C12B | 117.7 (2) |
C6A—C1A—C2A | 116.9 (2) | C10B—C11B—H11B | 121.1 |
C3A—C2A—C1A | 121.7 (2) | C12B—C11B—H11B | 121.1 |
C3A—C2A—N3A | 116.2 (2) | C11B—C12B—C13B | 120.9 (2) |
C1A—C2A—N3A | 122.1 (2) | C11B—C12B—H12B | 119.6 |
C4A—C3A—C2A | 118.7 (2) | C13B—C12B—H12B | 119.6 |
C4A—C3A—H3AA | 120.7 | C12B—C13B—C8B | 120.3 (2) |
C2A—C3A—H3AA | 120.7 | C12B—C13B—H13B | 119.8 |
C3A—C4A—C5A | 121.9 (2) | C8B—C13B—H13B | 119.8 |
C3A—C4A—N4A | 118.5 (2) | C7B—C14B—H14D | 109.5 |
C5A—C4A—N4A | 119.5 (2) | C7B—C14B—H14E | 109.5 |
C6A—C5A—C4A | 119.2 (2) | H14D—C14B—H14E | 109.5 |
C6A—C5A—H5AA | 120.4 | C7B—C14B—H14F | 109.5 |
C4A—C5A—H5AA | 120.4 | H14D—C14B—H14F | 109.5 |
C5A—C6A—C1A | 121.5 (2) | H14E—C14B—H14F | 109.5 |
C5A—C6A—H6AA | 119.2 | C1C—N1C—N2C | 119.8 (2) |
C1A—C6A—H6AA | 119.2 | C1C—N1C—H1CA | 120.1 |
N2A—C7A—C8A | 115.2 (2) | N2C—N1C—H1CA | 120.1 |
N2A—C7A—C14A | 125.4 (2) | C7C—N2C—N1C | 116.2 (2) |
C8A—C7A—C14A | 119.4 (2) | O2C—N3C—O1C | 122.3 (2) |
C13A—C8A—C9A | 119.0 (2) | O2C—N3C—C2C | 118.5 (2) |
C13A—C8A—C7A | 121.4 (2) | O1C—N3C—C2C | 119.3 (2) |
C9A—C8A—C7A | 119.6 (2) | O3C—N4C—O4C | 124.0 (2) |
C10A—C9A—C8A | 118.3 (2) | O3C—N4C—C4C | 118.3 (2) |
C10A—C9A—H9AA | 120.9 | O4C—N4C—C4C | 117.7 (2) |
C8A—C9A—H9AA | 120.9 | O5C—N5C—O6C | 123.7 (2) |
C11A—C10A—C9A | 123.1 (2) | O5C—N5C—C10C | 118.3 (2) |
C11A—C10A—N5A | 118.7 (2) | O6C—N5C—C10C | 118.0 (2) |
C9A—C10A—N5A | 118.2 (2) | N1C—C1C—C2C | 122.5 (2) |
C12A—C11A—C10A | 118.3 (2) | N1C—C1C—C6C | 120.3 (2) |
C12A—C11A—H11A | 120.9 | C2C—C1C—C6C | 117.1 (2) |
C10A—C11A—H11A | 120.9 | C3C—C2C—C1C | 121.4 (2) |
C11A—C12A—C13A | 120.4 (2) | C3C—C2C—N3C | 116.2 (2) |
C11A—C12A—H12A | 119.8 | C1C—C2C—N3C | 122.4 (2) |
C13A—C12A—H12A | 119.8 | C4C—C3C—C2C | 119.0 (2) |
C12A—C13A—C8A | 120.9 (2) | C4C—C3C—H3CA | 120.5 |
C12A—C13A—H13A | 119.6 | C2C—C3C—H3CA | 120.5 |
C8A—C13A—H13A | 119.6 | C3C—C4C—C5C | 121.9 (2) |
C7A—C14A—H14A | 109.5 | C3C—C4C—N4C | 118.7 (2) |
C7A—C14A—H14B | 109.5 | C5C—C4C—N4C | 119.5 (2) |
H14A—C14A—H14B | 109.5 | C6C—C5C—C4C | 119.1 (2) |
C7A—C14A—H14C | 109.5 | C6C—C5C—H5CA | 120.5 |
H14A—C14A—H14C | 109.5 | C4C—C5C—H5CA | 120.5 |
H14B—C14A—H14C | 109.5 | C5C—C6C—C1C | 121.4 (2) |
C1B—N1B—N2B | 118.5 (2) | C5C—C6C—H6CA | 119.3 |
C1B—N1B—H1BA | 120.7 | C1C—C6C—H6CA | 119.3 |
N2B—N1B—H1BA | 120.7 | N2C—C7C—C8C | 115.7 (2) |
C7B—N2B—N1B | 116.9 (2) | N2C—C7C—C14C | 125.0 (2) |
O2B—N3B—O1B | 123.1 (2) | C8C—C7C—C14C | 119.3 (2) |
O2B—N3B—C2B | 118.1 (2) | C9C—C8C—C13C | 119.0 (2) |
O1B—N3B—C2B | 118.9 (2) | C9C—C8C—C7C | 120.3 (2) |
O3B—N4B—O4B | 123.2 (2) | C13C—C8C—C7C | 120.7 (2) |
O3B—N4B—C4B | 118.1 (2) | C10C—C9C—C8C | 118.3 (2) |
O4B—N4B—C4B | 118.7 (2) | C10C—C9C—H9CA | 120.8 |
O6B—N5B—O5B | 123.4 (2) | C8C—C9C—H9CA | 120.8 |
O6B—N5B—C10B | 118.3 (2) | C11C—C10C—C9C | 123.3 (2) |
O5B—N5B—C10B | 118.3 (2) | C11C—C10C—N5C | 118.1 (2) |
N1B—C1B—C6B | 120.6 (2) | C9C—C10C—N5C | 118.6 (2) |
N1B—C1B—C2B | 122.4 (2) | C12C—C11C—C10C | 117.8 (2) |
C6B—C1B—C2B | 117.0 (2) | C12C—C11C—H11C | 121.1 |
C3B—C2B—C1B | 121.3 (2) | C10C—C11C—H11C | 121.1 |
C3B—C2B—N3B | 116.4 (2) | C11C—C12C—C13C | 120.8 (2) |
C1B—C2B—N3B | 122.3 (2) | C11C—C12C—H12C | 119.6 |
C4B—C3B—C2B | 119.4 (2) | C13C—C12C—H12C | 119.6 |
C4B—C3B—H3BA | 120.3 | C12C—C13C—C8C | 120.7 (2) |
C2B—C3B—H3BA | 120.3 | C12C—C13C—H13C | 119.6 |
C3B—C4B—C5B | 121.7 (2) | C8C—C13C—H13C | 119.6 |
C3B—C4B—N4B | 118.8 (2) | C7C—C14C—H14G | 109.5 |
C5B—C4B—N4B | 119.5 (2) | C7C—C14C—H14H | 109.5 |
C6B—C5B—C4B | 119.0 (2) | H14G—C14C—H14H | 109.5 |
C6B—C5B—H5BA | 120.5 | C7C—C14C—H14J | 109.5 |
C4B—C5B—H5BA | 120.5 | H14G—C14C—H14J | 109.5 |
C5B—C6B—C1B | 121.5 (2) | H14H—C14C—H14J | 109.5 |
C1A—N1A—N2A—C7A | −171.6 (2) | N1B—C1B—C6B—C5B | −177.7 (2) |
N2A—N1A—C1A—C6A | 4.3 (3) | C2B—C1B—C6B—C5B | 0.0 (3) |
N2A—N1A—C1A—C2A | −177.5 (2) | N1B—N2B—C7B—C8B | 177.9 (2) |
N1A—C1A—C2A—C3A | 179.3 (2) | N1B—N2B—C7B—C14B | −3.1 (4) |
C6A—C1A—C2A—C3A | −2.5 (3) | N2B—C7B—C8B—C9B | 19.2 (3) |
N1A—C1A—C2A—N3A | −1.2 (3) | C14B—C7B—C8B—C9B | −159.9 (2) |
C6A—C1A—C2A—N3A | 177.0 (2) | N2B—C7B—C8B—C13B | −160.4 (2) |
O2A—N3A—C2A—C3A | 0.1 (3) | C14B—C7B—C8B—C13B | 20.6 (3) |
O1A—N3A—C2A—C3A | 178.9 (2) | C13B—C8B—C9B—C10B | 1.0 (3) |
O2A—N3A—C2A—C1A | −179.4 (2) | C7B—C8B—C9B—C10B | −178.5 (2) |
O1A—N3A—C2A—C1A | −0.6 (3) | C8B—C9B—C10B—C11B | 0.5 (4) |
C1A—C2A—C3A—C4A | 2.8 (3) | C8B—C9B—C10B—N5B | −177.8 (2) |
N3A—C2A—C3A—C4A | −176.7 (2) | O6B—N5B—C10B—C11B | 12.8 (3) |
C2A—C3A—C4A—C5A | −0.4 (4) | O5B—N5B—C10B—C11B | −166.1 (2) |
C2A—C3A—C4A—N4A | 179.9 (2) | O6B—N5B—C10B—C9B | −168.8 (2) |
O3A—N4A—C4A—C3A | 19.8 (3) | O5B—N5B—C10B—C9B | 12.3 (3) |
O4A—N4A—C4A—C3A | −160.9 (2) | C9B—C10B—C11B—C12B | −1.1 (4) |
O3A—N4A—C4A—C5A | −159.9 (2) | N5B—C10B—C11B—C12B | 177.2 (2) |
O4A—N4A—C4A—C5A | 19.4 (3) | C10B—C11B—C12B—C13B | 0.2 (4) |
C3A—C4A—C5A—C6A | −2.3 (4) | C11B—C12B—C13B—C8B | 1.3 (4) |
N4A—C4A—C5A—C6A | 177.4 (2) | C9B—C8B—C13B—C12B | −1.9 (3) |
C4A—C5A—C6A—C1A | 2.6 (4) | C7B—C8B—C13B—C12B | 177.6 (2) |
N1A—C1A—C6A—C5A | 178.0 (2) | C1C—N1C—N2C—C7C | 170.1 (2) |
C2A—C1A—C6A—C5A | −0.2 (3) | N2C—N1C—C1C—C2C | −176.7 (2) |
N1A—N2A—C7A—C8A | −177.61 (19) | N2C—N1C—C1C—C6C | 1.4 (3) |
N1A—N2A—C7A—C14A | 2.6 (4) | N1C—C1C—C2C—C3C | 179.7 (2) |
N2A—C7A—C8A—C13A | 161.1 (2) | C6C—C1C—C2C—C3C | 1.5 (3) |
C14A—C7A—C8A—C13A | −19.1 (3) | N1C—C1C—C2C—N3C | 0.2 (4) |
N2A—C7A—C8A—C9A | −19.5 (3) | C6C—C1C—C2C—N3C | −178.0 (2) |
C14A—C7A—C8A—C9A | 160.3 (2) | O2C—N3C—C2C—C3C | −3.3 (3) |
C13A—C8A—C9A—C10A | −0.1 (3) | O1C—N3C—C2C—C3C | 177.1 (2) |
C7A—C8A—C9A—C10A | −179.6 (2) | O2C—N3C—C2C—C1C | 176.2 (2) |
C8A—C9A—C10A—C11A | −2.0 (4) | O1C—N3C—C2C—C1C | −3.4 (3) |
C8A—C9A—C10A—N5A | 176.1 (2) | C1C—C2C—C3C—C4C | −3.0 (4) |
O6A—N5A—C10A—C11A | −1.2 (4) | N3C—C2C—C3C—C4C | 176.5 (2) |
O5A—N5A—C10A—C11A | 176.2 (2) | C2C—C3C—C4C—C5C | 1.7 (4) |
O6A—N5A—C10A—C9A | −179.3 (2) | C2C—C3C—C4C—N4C | −177.7 (2) |
O5A—N5A—C10A—C9A | −1.9 (3) | O3C—N4C—C4C—C3C | −21.0 (3) |
C9A—C10A—C11A—C12A | 2.0 (4) | O4C—N4C—C4C—C3C | 159.4 (2) |
N5A—C10A—C11A—C12A | −176.0 (2) | O3C—N4C—C4C—C5C | 159.5 (2) |
C10A—C11A—C12A—C13A | 0.0 (4) | O4C—N4C—C4C—C5C | −20.1 (3) |
C11A—C12A—C13A—C8A | −2.0 (4) | C3C—C4C—C5C—C6C | 1.1 (4) |
C9A—C8A—C13A—C12A | 2.1 (4) | N4C—C4C—C5C—C6C | −179.4 (2) |
C7A—C8A—C13A—C12A | −178.5 (2) | C4C—C5C—C6C—C1C | −2.7 (4) |
C1B—N1B—N2B—C7B | 170.5 (2) | N1C—C1C—C6C—C5C | −176.8 (2) |
N2B—N1B—C1B—C6B | −0.9 (3) | C2C—C1C—C6C—C5C | 1.4 (3) |
N2B—N1B—C1B—C2B | −178.5 (2) | N1C—N2C—C7C—C8C | 178.35 (19) |
N1B—C1B—C2B—C3B | 178.2 (2) | N1C—N2C—C7C—C14C | −2.1 (3) |
C6B—C1B—C2B—C3B | 0.5 (3) | N2C—C7C—C8C—C9C | 11.8 (3) |
N1B—C1B—C2B—N3B | −1.1 (4) | C14C—C7C—C8C—C9C | −167.8 (2) |
C6B—C1B—C2B—N3B | −178.8 (2) | N2C—C7C—C8C—C13C | −168.6 (2) |
O2B—N3B—C2B—C3B | −12.4 (3) | C14C—C7C—C8C—C13C | 11.9 (3) |
O1B—N3B—C2B—C3B | 167.4 (2) | C13C—C8C—C9C—C10C | −1.0 (3) |
O2B—N3B—C2B—C1B | 167.0 (2) | C7C—C8C—C9C—C10C | 178.7 (2) |
O1B—N3B—C2B—C1B | −13.2 (3) | C8C—C9C—C10C—C11C | 1.5 (4) |
C1B—C2B—C3B—C4B | −0.1 (4) | C8C—C9C—C10C—N5C | −176.7 (2) |
N3B—C2B—C3B—C4B | 179.2 (2) | O5C—N5C—C10C—C11C | −175.2 (2) |
C2B—C3B—C4B—C5B | −0.8 (4) | O6C—N5C—C10C—C11C | 3.1 (3) |
C2B—C3B—C4B—N4B | 178.4 (2) | O5C—N5C—C10C—C9C | 3.1 (3) |
O3B—N4B—C4B—C3B | −9.8 (4) | O6C—N5C—C10C—C9C | −178.5 (2) |
O4B—N4B—C4B—C3B | 170.6 (2) | C9C—C10C—C11C—C12C | −0.7 (4) |
O3B—N4B—C4B—C5B | 169.4 (3) | N5C—C10C—C11C—C12C | 177.5 (2) |
O4B—N4B—C4B—C5B | −10.2 (4) | C10C—C11C—C12C—C13C | −0.6 (4) |
C3B—C4B—C5B—C6B | 1.3 (4) | C11C—C12C—C13C—C8C | 1.1 (4) |
N4B—C4B—C5B—C6B | −177.9 (2) | C9C—C8C—C13C—C12C | −0.3 (3) |
C4B—C5B—C6B—C1B | −0.9 (4) | C7C—C8C—C13C—C12C | −179.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1A | 0.88 | 1.98 | 2.615 (3) | 128 |
N1B—H1BA···O1B | 0.88 | 2.01 | 2.637 (3) | 127 |
N1C—H1CA···O1C | 0.88 | 1.98 | 2.617 (3) | 129 |
C3A—H3AA···O2Ai | 0.95 | 2.44 | 3.320 (3) | 154 |
C3B—H3BA···O2Cii | 0.95 | 2.40 | 3.188 (3) | 140 |
C3C—H3CA···O2Biii | 0.95 | 2.52 | 3.413 (3) | 156 |
C14B—H14F···O4Aiv | 0.98 | 2.53 | 3.316 (4) | 137 |
C14C—H14J···O4Ciii | 0.98 | 2.54 | 3.253 (4) | 129 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) x−1, −y+3/2, z−1/2; (iv) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H11N5O6 |
Mr | 345.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.3309 (2), 38.3569 (8), 16.8027 (4) |
β (°) | 115.158 (1) |
V (Å3) | 4276.57 (18) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.49 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.940, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49752, 12460, 7719 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.159, 1.07 |
No. of reflections | 12460 |
No. of parameters | 679 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.38 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1A | 0.88 | 1.98 | 2.615 (3) | 128 |
N1B—H1BA···O1B | 0.88 | 2.01 | 2.637 (3) | 127 |
N1C—H1CA···O1C | 0.88 | 1.98 | 2.617 (3) | 129 |
C3A—H3AA···O2Ai | 0.95 | 2.44 | 3.320 (3) | 154 |
C3B—H3BA···O2Cii | 0.95 | 2.40 | 3.188 (3) | 140 |
C3C—H3CA···O2Biii | 0.95 | 2.52 | 3.413 (3) | 156 |
C14B—H14F···O4Aiv | 0.98 | 2.53 | 3.316 (4) | 137 |
C14C—H14J···O4Ciii | 0.98 | 2.54 | 3.253 (4) | 129 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) x−1, −y+3/2, z−1/2; (iv) x+1, y, z+1. |
Acknowledgements
BN and TK thank the Crystal Materials Research Unit, Prince of Songkla University, for financial support. NB thanks Prince of Songkla University for a postdoctoral fellowship. The authors thank Prince of Songkla University and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Considerable attentions have been devoted to hydrazones and their complexes which have been acknowledged to possess diverse biological properties as antibacterial, antifungal, anagesic, anti-inflammatory as well as antioxidant activities (Cui et al., 2010; Krishnamoorthy et al., 2011; Raja et al., 2012; Sathyadevi et al., 2012). In our on-going research on bioactivity of hydrazones, the title compound (I) was synthesized and evaluated for antioxidant activity by DPPH scavenging (Molyneux, 2004) and was found to be weakly active with 30% inhibition. It was also screened for antibacterial activity and found to be inactive. Herein we report the synthesis and crystal structure of (I).
In the asymmetric unit of (I), C14H11N5O6, there are three crystallographically independent molecules A, B and C with similar conformations but some differences in bond angles (Fig. 1). The molecular structure is slightly twisted with the dihedral angle between the two benzene rings being 10.02 (14), 8.41 (15) and 1.40 (14)° in molecule A, B and C, respectively. The central ethylidenehydrazine bridge is planar with the torsion angles N1–N2–C7–C14 = 2.6 (4), -3.1 (4) and -2.1 (3)° in molecules A, B and C, respectively. This central N1/N2/C7/C14 plane makes dihedral angles of 12.90 (18) and 20.11 (18)° with the 2,4-dinitro- and 3-nitro-substituted benzene rings, respectively in molecule A, whereas the corresponding values are 12.50 (18) and 20.51 (18)° in molecule B, and 11.70 (18) and 12.33 (18)° in molecule C. In all three molecules, the nitro group of 3-nitrophenyl are co-planar with their bound benzene rings with r.m.s. deviations of 0.079 (2), 0.030 (2) and 0.025 (3) Å in molecules A, B and C, respectively, for the nine non H-atoms (C8–C13/N5/O5–O6). In the 2,4-dinitrophenyl, the ortho-nitro group lies on the same plane with its bound benzene ring with r.m.s. deviations of 0.023 (2), 0.075 (2) and 0.025 (2) Å in molecules A, B and C, repectively, for the nine non H-atoms (C1–C6/N3/O1–O2), but the para-nitro group is deviated with the torsion angles O3–N4–C4–C3 = 19.8 (3)° and O4–N4–C4–C3 = -160.9 (2)° in molecule A whereas the corresponding values are -9.8 (4) and 170.6 (2)° in molecule B, and -21.0 (3) and 159.4 (2)° in molecule C. In each molecule, intramolecular N—H···O hydrogen bonds between the hydrazone-NH and the ortho-nitro group (Fig. 1 and Table 1) generate three S(6) ring motifs (Bernstein et al., 1995). The bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structure (Chantrapromma et al., 2011).
In the crystal structure (Fig. 2), the molecules are linked by C—H···O weak interactions (Table 1) into a three-dimensional network. π–π interactions were presented with the distances of Cg1···Cg6 = 3.5635 (17) Å, Cg2···Cg5 = 3.5650 (18) Å, Cg3···Cg4v = 3.6544 (18) Å and Cg3···Cg4vi = 3.8273 (18) Å [symmetry codes: (v) 1 - x, 2 - y, 2 - z; (vi) 2 - x, 2 - y, 2 - z]; Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of C1A–C6A, C8A–C13A, C1B–C6B, C8B–C13BA, C1C–C6C and C8C–C13C benzene rings, respectively.