organic compounds
3-(1H-Imidazol-1-yl)propanaminium picrate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-trinitrophenolate], C6H12N3+·C6H2N3O7−, there are five independent cation–anion pairs (A, B, C, D, E) in the In the cation, the ammonium group is protonated with the aminopropyl group nearly at right angles to the mean plane of the imidazole ring showing C—N—C—C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H⋯O cation–anion and N—H⋯N cation–cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C—H⋯O cation–anion interactions occur.
CCDC reference: 961387
Related literature
For pharmacological properties of imidazole compounds, see: Lombardino & Wiseman (1974). For applications of substituted imidazoles, see: Maier et al. (1989a,b). For imidazole derivatives as anticancer agents, see: Krezel (1998). For electrostatic or hydrogen-bonding interactions in picric acid charge-transfer complexes, see: In et al. (1997). For imidazolium-based cation picrate salts as good candidates for energetic ionic salts, see: Jin et al. (2005). For the of imidazolium picrate, see: Soriano-García et al. (1990) and for the structures of of some other imidazole derivatives, see: Du & Zhao (2003); Dutkiewicz et al. (2011); MacDonald et al. (2005); Nardelli et al. (1987); Pi et al. (2009). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 961387
10.1107/S1600536813025646/sj5352sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025646/sj5352Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813025646/sj5352Isup3.cml
Commercially available 1-(3-aminopropyl)imidazole (0.5 g, 3.99 mmol) and picric acid (1.19 g, 3.99 mmol) were dissolved in 10 ml of ethanol and stirred for 5 minutes at room temperature. After 30 mins, crystals were formed on evaporation of ethanol (m.p.: 370–373 K).
H6AA, H6AB, H6AC, H6BA, H6BB, H6BC, H6CA, H6CB, H6CC, H6DA, H6DB, H6DC, H6EA, H6EB, H6EC, were located by a difference map and refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (aromatic) or 0.99Å (CH2). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2) times Ueq of the parent atom. Disorder is observed in atom O5D of anion D with an occupancy ratio of 0.53 (5):0.47 (5).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).Fig. 1. ORTEP drawing of one of five independent cation (C6H12N3+ ) and anion (C6H2N3O7-) pairs (C) in the asymmetric unit of (I), for clarity, showing the atom labeling scheme and 30% probability displacement ellipsoids. | |
Fig. 2. Molecular packing for (I) viewed along the c axis. Dashed lines indicate N—H···O cation–anion and N—H···N cation-cation hydrogen bonds, dahed lines, linking the ions into chains along [0 1 0]. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. |
C6H12N3+·C6H2N3O7− | F(000) = 3680 |
Mr = 354.29 | Dx = 1.556 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 11.98275 (18) Å | Cell parameters from 17325 reflections |
b = 38.5234 (6) Å | θ = 3.4–72.3° |
c = 16.4239 (2) Å | µ = 1.13 mm−1 |
β = 94.1970 (14)° | T = 173 K |
V = 7561.2 (2) Å3 | Irregular, clear yellow |
Z = 20 | 0.21 × 0.17 × 0.08 mm |
Agilent Xcalibur (Eos, Gemini) diffractometer | 14795 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 12167 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.032 |
ω scans | θmax = 72.5°, θmin = 3.5° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | h = −9→14 |
Tmin = 0.870, Tmax = 1.000 | k = −47→46 |
52087 measured reflections | l = −20→20 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0585P)2 + 2.3598P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.51 e Å−3 |
14795 reflections | Δρmin = −0.29 e Å−3 |
1197 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
12 restraints | Extinction coefficient: 0.000142 (14) |
C6H12N3+·C6H2N3O7− | V = 7561.2 (2) Å3 |
Mr = 354.29 | Z = 20 |
Monoclinic, P21/n | Cu Kα radiation |
a = 11.98275 (18) Å | µ = 1.13 mm−1 |
b = 38.5234 (6) Å | T = 173 K |
c = 16.4239 (2) Å | 0.21 × 0.17 × 0.08 mm |
β = 94.1970 (14)° |
Agilent Xcalibur (Eos, Gemini) diffractometer | 14795 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 12167 reflections with I > 2σ(I) |
Tmin = 0.870, Tmax = 1.000 | Rint = 0.032 |
52087 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 12 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.51 e Å−3 |
14795 reflections | Δρmin = −0.29 e Å−3 |
1197 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 0.06660 (12) | 0.70857 (4) | 0.28122 (10) | 0.0543 (4) | |
O2A | 0.03780 (11) | 0.68796 (4) | 0.40019 (10) | 0.0477 (4) | |
O3A | 0.11234 (9) | 0.62090 (3) | 0.40908 (7) | 0.0296 (3) | |
O4A | 0.21360 (12) | 0.56043 (3) | 0.37863 (10) | 0.0491 (4) | |
O5A | 0.39119 (12) | 0.56511 (4) | 0.39119 (12) | 0.0636 (5) | |
O6A | 0.55513 (10) | 0.65993 (4) | 0.25325 (8) | 0.0417 (3) | |
O7A | 0.46158 (11) | 0.70758 (4) | 0.23205 (9) | 0.0446 (3) | |
N1A | 0.09133 (12) | 0.68950 (4) | 0.33963 (10) | 0.0329 (3) | |
N2A | 0.29916 (12) | 0.57781 (4) | 0.37670 (9) | 0.0321 (3) | |
N3A | 0.47021 (12) | 0.67773 (4) | 0.25701 (9) | 0.0318 (3) | |
C1A | 0.27832 (13) | 0.68191 (4) | 0.29857 (10) | 0.0259 (3) | |
H1A | 0.2729 | 0.7046 | 0.2761 | 0.031* | |
C2A | 0.19050 (12) | 0.66773 (4) | 0.33624 (10) | 0.0245 (3) | |
C3A | 0.18956 (12) | 0.63312 (4) | 0.37119 (9) | 0.0224 (3) | |
C4A | 0.29093 (13) | 0.61429 (4) | 0.35572 (9) | 0.0246 (3) | |
C5A | 0.38185 (13) | 0.62869 (4) | 0.32185 (9) | 0.0260 (3) | |
H5A | 0.4482 | 0.6155 | 0.3178 | 0.031* | |
C6A | 0.37572 (13) | 0.66236 (4) | 0.29393 (9) | 0.0260 (3) | |
O1B | 0.41038 (10) | 0.62930 (3) | 0.10159 (8) | 0.0377 (3) | |
O2B | 0.50153 (9) | 0.58259 (3) | 0.13563 (9) | 0.0385 (3) | |
O3B | 0.37850 (9) | 0.52841 (3) | 0.06265 (7) | 0.0261 (2) | |
O4B | 0.25989 (12) | 0.47144 (3) | 0.10774 (9) | 0.0432 (3) | |
O5B | 0.08374 (12) | 0.48134 (4) | 0.08146 (10) | 0.0571 (4) | |
O6B | −0.05515 (10) | 0.58211 (4) | 0.20725 (8) | 0.0392 (3) | |
O7B | 0.04050 (10) | 0.62992 (3) | 0.20991 (8) | 0.0386 (3) | |
N1B | 0.02960 (11) | 0.59876 (4) | 0.19519 (8) | 0.0299 (3) | |
N2B | 0.17976 (12) | 0.49122 (4) | 0.10008 (9) | 0.0331 (3) | |
N3B | 0.41401 (11) | 0.59841 (3) | 0.11880 (8) | 0.0243 (3) | |
C1B | 0.22192 (12) | 0.59790 (4) | 0.15207 (9) | 0.0232 (3) | |
H1B | 0.2297 | 0.6219 | 0.1648 | 0.028* | |
C2B | 0.12167 (13) | 0.58070 (4) | 0.16165 (9) | 0.0255 (3) | |
C3B | 0.10926 (13) | 0.54597 (4) | 0.14262 (9) | 0.0253 (3) | |
H3B | 0.0402 | 0.5345 | 0.1490 | 0.030* | |
C4B | 0.19756 (13) | 0.52809 (4) | 0.11443 (9) | 0.0249 (3) | |
C5B | 0.30432 (12) | 0.54352 (4) | 0.09843 (9) | 0.0209 (3) | |
C6B | 0.30933 (12) | 0.57958 (4) | 0.12386 (9) | 0.0214 (3) | |
O1C | 0.93330 (11) | 0.49777 (4) | 0.71717 (9) | 0.0459 (3) | |
O2C | 0.95844 (11) | 0.51289 (4) | 0.59358 (10) | 0.0504 (4) | |
O3C | 0.85836 (9) | 0.57635 (3) | 0.56438 (7) | 0.0274 (2) | |
O4C | 0.70931 (11) | 0.63065 (3) | 0.55889 (8) | 0.0392 (3) | |
O5C | 0.54488 (11) | 0.60950 (4) | 0.52653 (10) | 0.0488 (4) | |
O6C | 0.42608 (9) | 0.52706 (3) | 0.72080 (8) | 0.0357 (3) | |
O7C | 0.53457 (10) | 0.48321 (3) | 0.75141 (8) | 0.0400 (3) | |
N1C | 0.90358 (11) | 0.51276 (4) | 0.65333 (9) | 0.0307 (3) | |
N2C | 0.64000 (12) | 0.60737 (4) | 0.56060 (9) | 0.0306 (3) | |
N3C | 0.51685 (11) | 0.51198 (4) | 0.72106 (8) | 0.0287 (3) | |
C1C | 0.71259 (13) | 0.51435 (4) | 0.68752 (9) | 0.0237 (3) | |
H1C | 0.7274 | 0.4937 | 0.7180 | 0.028* | |
C2C | 0.79609 (12) | 0.53034 (4) | 0.64799 (9) | 0.0230 (3) | |
C3C | 0.78325 (12) | 0.56224 (4) | 0.60164 (9) | 0.0217 (3) | |
C4C | 0.67031 (13) | 0.57559 (4) | 0.60354 (9) | 0.0243 (3) | |
C5C | 0.58477 (13) | 0.55929 (4) | 0.63995 (9) | 0.0255 (3) | |
H5C | 0.5116 | 0.5689 | 0.6361 | 0.031* | |
C6C | 0.60648 (12) | 0.52896 (4) | 0.68195 (9) | 0.0241 (3) | |
O1D | 0.43842 (13) | 0.41609 (4) | 0.17945 (13) | 0.0753 (6) | |
O2D | 0.45803 (12) | 0.38759 (4) | 0.06991 (9) | 0.0483 (4) | |
O3D | 0.39104 (9) | 0.32112 (3) | 0.09394 (8) | 0.0321 (3) | |
O4D | 0.27366 (16) | 0.26401 (4) | 0.11869 (13) | 0.0756 (6) | |
O5D | 0.1088 (5) | 0.2689 (2) | 0.132 (2) | 0.074 (6) | 0.53 (5) |
O5DA | 0.1161 (9) | 0.2685 (2) | 0.1739 (14) | 0.051 (3) | 0.47 (5) |
O6D | −0.04727 (10) | 0.37181 (4) | 0.23998 (8) | 0.0417 (3) | |
O7D | 0.04676 (10) | 0.41989 (3) | 0.24429 (8) | 0.0392 (3) | |
N1D | 0.41073 (12) | 0.39325 (4) | 0.13245 (10) | 0.0335 (3) | |
N2D | 0.19780 (13) | 0.28171 (4) | 0.13810 (9) | 0.0346 (3) | |
N3D | 0.03733 (11) | 0.38876 (4) | 0.22938 (8) | 0.0310 (3) | |
C1D | 0.22787 (13) | 0.38939 (4) | 0.18260 (10) | 0.0259 (3) | |
H1D | 0.2349 | 0.4132 | 0.1972 | 0.031* | |
C2D | 0.31297 (13) | 0.37241 (4) | 0.14767 (10) | 0.0246 (3) | |
C3D | 0.31268 (12) | 0.33593 (4) | 0.12588 (9) | 0.0237 (3) | |
C4D | 0.21039 (13) | 0.31897 (4) | 0.14756 (9) | 0.0258 (3) | |
C5D | 0.12236 (13) | 0.33613 (4) | 0.17907 (10) | 0.0271 (3) | |
H5D | 0.0559 | 0.3239 | 0.1889 | 0.033* | |
C6D | 0.13078 (13) | 0.37097 (4) | 0.19620 (10) | 0.0266 (3) | |
O1E | 0.08024 (11) | 0.32801 (3) | 0.38651 (11) | 0.0522 (4) | |
O2E | 0.00509 (10) | 0.27786 (3) | 0.36309 (9) | 0.0387 (3) | |
O3E | 0.14077 (9) | 0.23016 (3) | 0.45016 (7) | 0.0273 (2) | |
O4E | 0.28681 (12) | 0.17609 (3) | 0.42987 (9) | 0.0453 (3) | |
O5E | 0.45292 (11) | 0.19515 (4) | 0.46414 (11) | 0.0559 (4) | |
O6E | 0.56176 (10) | 0.29016 (4) | 0.29897 (8) | 0.0429 (3) | |
O7E | 0.45539 (11) | 0.33582 (4) | 0.29169 (8) | 0.0457 (3) | |
N1E | 0.08694 (11) | 0.29654 (3) | 0.37717 (8) | 0.0274 (3) | |
N2E | 0.35637 (12) | 0.19938 (4) | 0.43450 (10) | 0.0344 (3) | |
N3E | 0.47330 (12) | 0.30510 (4) | 0.30897 (8) | 0.0337 (3) | |
C1E | 0.28020 (13) | 0.30019 (4) | 0.34811 (9) | 0.0261 (3) | |
H1E | 0.2658 | 0.3233 | 0.3298 | 0.031* | |
C2E | 0.19720 (12) | 0.28065 (4) | 0.37890 (9) | 0.0236 (3) | |
C3E | 0.21231 (12) | 0.24610 (4) | 0.41326 (9) | 0.0221 (3) | |
C4E | 0.32526 (13) | 0.23366 (4) | 0.40462 (10) | 0.0249 (3) | |
C5E | 0.40861 (13) | 0.25255 (4) | 0.37280 (9) | 0.0265 (3) | |
H5E | 0.4814 | 0.2430 | 0.3705 | 0.032* | |
C6E | 0.38536 (13) | 0.28565 (4) | 0.34421 (9) | 0.0270 (3) | |
N4A | 0.75790 (11) | 0.09105 (3) | 0.43652 (9) | 0.0303 (3) | |
N5A | 0.69358 (11) | 0.14260 (3) | 0.39781 (8) | 0.0244 (3) | |
N6A | 0.90342 (12) | 0.23186 (3) | 0.47233 (9) | 0.0253 (3) | |
H6AA | 0.9724 (18) | 0.2348 (5) | 0.4655 (12) | 0.032 (5)* | |
H6AB | 0.8939 (15) | 0.2239 (5) | 0.5237 (13) | 0.030 (5)* | |
H6AC | 0.8659 (16) | 0.2535 (5) | 0.4655 (12) | 0.034 (5)* | |
C7A | 0.66412 (14) | 0.09844 (4) | 0.47645 (10) | 0.0295 (3) | |
H7A | 0.6323 | 0.0835 | 0.5146 | 0.035* | |
C8A | 0.77269 (13) | 0.11818 (4) | 0.38983 (11) | 0.0276 (3) | |
H8A | 0.8319 | 0.1203 | 0.3547 | 0.033* | |
C9A | 0.62334 (13) | 0.13017 (4) | 0.45358 (10) | 0.0279 (3) | |
H9A | 0.5595 | 0.1414 | 0.4723 | 0.033* | |
C10A | 0.68255 (14) | 0.17569 (4) | 0.35409 (10) | 0.0284 (3) | |
H10A | 0.6025 | 0.1801 | 0.3383 | 0.034* | |
H10B | 0.7224 | 0.1742 | 0.3035 | 0.034* | |
C11A | 0.72981 (13) | 0.20599 (4) | 0.40554 (11) | 0.0271 (3) | |
H11A | 0.7011 | 0.2281 | 0.3812 | 0.033* | |
H11B | 0.7038 | 0.2042 | 0.4612 | 0.033* | |
C12A | 0.85708 (13) | 0.20646 (4) | 0.41082 (11) | 0.0277 (3) | |
H12A | 0.8856 | 0.1830 | 0.4255 | 0.033* | |
H12B | 0.8830 | 0.2125 | 0.3567 | 0.033* | |
N4B | 0.73741 (12) | 0.39002 (3) | 0.09045 (10) | 0.0337 (3) | |
N5B | 0.80676 (11) | 0.44049 (3) | 0.13254 (8) | 0.0250 (3) | |
N6B | 0.61280 (11) | 0.53074 (3) | 0.04321 (9) | 0.0245 (3) | |
H6BA | 0.6219 (15) | 0.5212 (5) | −0.0074 (12) | 0.029 (5)* | |
H6BB | 0.5412 (18) | 0.5353 (5) | 0.0484 (12) | 0.040 (6)* | |
H6BC | 0.6517 (15) | 0.5514 (5) | 0.0468 (11) | 0.029 (5)* | |
C7B | 0.83655 (14) | 0.39557 (4) | 0.05633 (11) | 0.0305 (4) | |
H7B | 0.8699 | 0.3800 | 0.0204 | 0.037* | |
C8B | 0.72217 (14) | 0.41758 (4) | 0.13569 (11) | 0.0309 (4) | |
H8B | 0.6592 | 0.4209 | 0.1668 | 0.037* | |
C9B | 0.88023 (13) | 0.42658 (4) | 0.08124 (10) | 0.0280 (3) | |
H9B | 0.9481 | 0.4367 | 0.0662 | 0.034* | |
C10B | 0.81931 (14) | 0.47403 (4) | 0.17389 (10) | 0.0288 (3) | |
H10C | 0.8990 | 0.4776 | 0.1924 | 0.035* | |
H10D | 0.7757 | 0.4739 | 0.2228 | 0.035* | |
C11B | 0.77981 (13) | 0.50414 (4) | 0.11863 (10) | 0.0265 (3) | |
H11C | 0.8114 | 0.5261 | 0.1416 | 0.032* | |
H11D | 0.8080 | 0.5008 | 0.0640 | 0.032* | |
C12B | 0.65295 (13) | 0.50676 (4) | 0.11003 (10) | 0.0269 (3) | |
H12C | 0.6209 | 0.4834 | 0.0989 | 0.032* | |
H12D | 0.6260 | 0.5151 | 0.1621 | 0.032* | |
N4C | 0.77635 (12) | 0.29279 (3) | 0.44507 (10) | 0.0333 (3) | |
N5C | 0.71008 (11) | 0.34335 (3) | 0.40054 (9) | 0.0267 (3) | |
N6C | 0.91077 (12) | 0.43386 (3) | 0.47087 (9) | 0.0238 (3) | |
H6CA | 0.9797 (17) | 0.4372 (5) | 0.4660 (11) | 0.027 (5)* | |
H6CB | 0.9011 (15) | 0.4268 (5) | 0.5215 (12) | 0.026 (5)* | |
H6CC | 0.8729 (16) | 0.4547 (5) | 0.4643 (12) | 0.034 (5)* | |
C7C | 0.68308 (15) | 0.30101 (4) | 0.48517 (11) | 0.0326 (4) | |
H7C | 0.6523 | 0.2870 | 0.5255 | 0.039* | |
C8C | 0.64165 (14) | 0.33207 (4) | 0.45851 (11) | 0.0310 (4) | |
H8C | 0.5779 | 0.3437 | 0.4764 | 0.037* | |
C9C | 0.78943 (14) | 0.31884 (4) | 0.39487 (11) | 0.0302 (4) | |
H9C | 0.8478 | 0.3202 | 0.3589 | 0.036* | |
C10C | 0.69767 (14) | 0.37533 (4) | 0.35294 (11) | 0.0300 (4) | |
H10E | 0.6176 | 0.3788 | 0.3355 | 0.036* | |
H10F | 0.7390 | 0.3730 | 0.3032 | 0.036* | |
C11C | 0.74117 (13) | 0.40700 (4) | 0.40111 (11) | 0.0278 (3) | |
H11E | 0.7123 | 0.4283 | 0.3733 | 0.033* | |
H11F | 0.7129 | 0.4064 | 0.4562 | 0.033* | |
C12C | 0.86828 (13) | 0.40808 (4) | 0.40902 (10) | 0.0273 (3) | |
H12E | 0.8975 | 0.3848 | 0.4247 | 0.033* | |
H12F | 0.8961 | 0.4141 | 0.3555 | 0.033* | |
N4D | 0.22010 (12) | 0.50702 (3) | 0.56986 (9) | 0.0317 (3) | |
N5D | 0.28930 (11) | 0.46050 (3) | 0.63391 (8) | 0.0258 (3) | |
N6D | 0.11287 (12) | 0.36876 (3) | 0.55463 (9) | 0.0233 (3) | |
H6DA | 0.0399 (17) | 0.3640 (5) | 0.5526 (11) | 0.029 (5)* | |
H6DB | 0.1314 (16) | 0.3766 (5) | 0.5062 (13) | 0.035 (5)* | |
H6DC | 0.1483 (15) | 0.3488 (5) | 0.5657 (11) | 0.028 (5)* | |
C7D | 0.36432 (14) | 0.47005 (4) | 0.57872 (10) | 0.0298 (3) | |
H7D | 0.4329 | 0.4589 | 0.5693 | 0.036* | |
C8D | 0.20416 (13) | 0.48345 (4) | 0.62573 (10) | 0.0277 (3) | |
H8D | 0.1403 | 0.4827 | 0.6567 | 0.033* | |
C9D | 0.32091 (14) | 0.49861 (4) | 0.54037 (11) | 0.0318 (4) | |
H9D | 0.3553 | 0.5111 | 0.4990 | 0.038* | |
C10D | 0.29807 (14) | 0.43027 (4) | 0.68810 (10) | 0.0289 (3) | |
H10G | 0.2483 | 0.4336 | 0.7330 | 0.035* | |
H10H | 0.3758 | 0.4284 | 0.7126 | 0.035* | |
C11D | 0.26634 (13) | 0.39670 (4) | 0.64306 (10) | 0.0271 (3) | |
H11G | 0.3086 | 0.3950 | 0.5937 | 0.033* | |
H11H | 0.2875 | 0.3767 | 0.6787 | 0.033* | |
C12D | 0.14198 (13) | 0.39512 (4) | 0.61840 (10) | 0.0282 (3) | |
H12G | 0.1013 | 0.3898 | 0.6672 | 0.034* | |
H12H | 0.1167 | 0.4182 | 0.5979 | 0.034* | |
N4E | 0.23642 (12) | 0.30890 (4) | 0.59484 (10) | 0.0341 (3) | |
N5E | 0.30112 (11) | 0.26041 (3) | 0.65175 (8) | 0.0264 (3) | |
N6E | 0.11830 (12) | 0.17068 (3) | 0.55652 (9) | 0.0244 (3) | |
H6EA | 0.0441 (19) | 0.1656 (5) | 0.5537 (13) | 0.040 (6)* | |
H6EB | 0.1349 (16) | 0.1796 (5) | 0.5102 (13) | 0.031 (5)* | |
H6EC | 0.1545 (17) | 0.1495 (5) | 0.5656 (12) | 0.038 (5)* | |
C7E | 0.34032 (15) | 0.30216 (4) | 0.56911 (11) | 0.0334 (4) | |
H7E | 0.3782 | 0.3163 | 0.5326 | 0.040* | |
C8E | 0.21567 (14) | 0.28319 (4) | 0.64442 (11) | 0.0308 (4) | |
H8E | 0.1488 | 0.2810 | 0.6716 | 0.037* | |
C9E | 0.38128 (14) | 0.27238 (4) | 0.60320 (11) | 0.0314 (4) | |
H9E | 0.4514 | 0.2619 | 0.5952 | 0.038* | |
C10E | 0.30688 (15) | 0.22809 (4) | 0.69875 (10) | 0.0309 (4) | |
H10I | 0.2562 | 0.2298 | 0.7436 | 0.037* | |
H10J | 0.3840 | 0.2249 | 0.7235 | 0.037* | |
C11E | 0.27412 (14) | 0.19658 (4) | 0.64595 (11) | 0.0289 (3) | |
H11I | 0.3144 | 0.1974 | 0.5955 | 0.035* | |
H11J | 0.2970 | 0.1751 | 0.6759 | 0.035* | |
C12E | 0.14910 (13) | 0.19551 (4) | 0.62346 (10) | 0.0285 (3) | |
H12I | 0.1101 | 0.1889 | 0.6722 | 0.034* | |
H12J | 0.1233 | 0.2190 | 0.6066 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0449 (8) | 0.0491 (9) | 0.0694 (10) | 0.0187 (7) | 0.0076 (7) | 0.0317 (8) |
O2A | 0.0382 (7) | 0.0381 (7) | 0.0701 (10) | 0.0121 (6) | 0.0267 (7) | 0.0157 (7) |
O3A | 0.0234 (6) | 0.0277 (6) | 0.0385 (7) | 0.0032 (4) | 0.0086 (5) | 0.0102 (5) |
O4A | 0.0497 (8) | 0.0259 (7) | 0.0754 (10) | −0.0009 (6) | 0.0289 (7) | 0.0023 (6) |
O5A | 0.0416 (8) | 0.0411 (8) | 0.1072 (14) | 0.0184 (7) | −0.0008 (8) | 0.0171 (9) |
O6A | 0.0233 (6) | 0.0594 (9) | 0.0435 (7) | 0.0038 (6) | 0.0105 (5) | 0.0068 (6) |
O7A | 0.0383 (7) | 0.0441 (8) | 0.0531 (8) | −0.0064 (6) | 0.0156 (6) | 0.0134 (6) |
N1A | 0.0243 (7) | 0.0262 (7) | 0.0490 (9) | 0.0023 (6) | 0.0077 (6) | 0.0102 (6) |
N2A | 0.0376 (8) | 0.0271 (7) | 0.0323 (8) | 0.0070 (6) | 0.0076 (6) | 0.0011 (6) |
N3A | 0.0255 (7) | 0.0429 (9) | 0.0275 (7) | −0.0041 (6) | 0.0058 (6) | 0.0023 (6) |
C1A | 0.0260 (8) | 0.0261 (8) | 0.0257 (8) | −0.0018 (6) | 0.0018 (6) | 0.0033 (6) |
C2A | 0.0202 (7) | 0.0255 (8) | 0.0278 (8) | 0.0017 (6) | 0.0018 (6) | 0.0035 (6) |
C3A | 0.0203 (7) | 0.0244 (8) | 0.0221 (7) | −0.0002 (6) | −0.0003 (6) | 0.0012 (6) |
C4A | 0.0261 (8) | 0.0250 (8) | 0.0226 (7) | 0.0023 (6) | 0.0011 (6) | 0.0014 (6) |
C5A | 0.0216 (8) | 0.0341 (9) | 0.0227 (8) | 0.0043 (6) | 0.0026 (6) | −0.0016 (6) |
C6A | 0.0219 (8) | 0.0336 (9) | 0.0229 (8) | −0.0027 (6) | 0.0045 (6) | −0.0003 (6) |
O1B | 0.0373 (7) | 0.0221 (6) | 0.0538 (8) | −0.0069 (5) | 0.0042 (6) | 0.0045 (5) |
O2B | 0.0200 (6) | 0.0304 (6) | 0.0647 (9) | −0.0008 (5) | 0.0011 (5) | −0.0070 (6) |
O3B | 0.0235 (5) | 0.0231 (5) | 0.0322 (6) | −0.0030 (4) | 0.0061 (4) | −0.0062 (4) |
O4B | 0.0530 (8) | 0.0236 (6) | 0.0551 (8) | −0.0036 (6) | 0.0182 (7) | −0.0002 (6) |
O5B | 0.0431 (8) | 0.0511 (9) | 0.0791 (11) | −0.0284 (7) | 0.0180 (8) | −0.0235 (8) |
O6B | 0.0230 (6) | 0.0589 (8) | 0.0369 (7) | 0.0004 (6) | 0.0098 (5) | −0.0014 (6) |
O7B | 0.0309 (6) | 0.0438 (8) | 0.0407 (7) | 0.0103 (5) | −0.0015 (5) | −0.0134 (6) |
N1B | 0.0236 (7) | 0.0428 (8) | 0.0231 (7) | 0.0060 (6) | 0.0000 (5) | −0.0044 (6) |
N2B | 0.0387 (8) | 0.0298 (8) | 0.0325 (8) | −0.0143 (6) | 0.0147 (6) | −0.0058 (6) |
N3B | 0.0232 (7) | 0.0208 (6) | 0.0295 (7) | −0.0022 (5) | 0.0050 (5) | −0.0039 (5) |
C1B | 0.0250 (8) | 0.0230 (7) | 0.0212 (7) | 0.0012 (6) | −0.0017 (6) | −0.0012 (6) |
C2B | 0.0207 (7) | 0.0349 (9) | 0.0208 (7) | 0.0031 (6) | 0.0014 (6) | −0.0009 (6) |
C3B | 0.0214 (7) | 0.0341 (9) | 0.0206 (7) | −0.0067 (6) | 0.0031 (6) | 0.0010 (6) |
C4B | 0.0278 (8) | 0.0252 (8) | 0.0220 (7) | −0.0067 (6) | 0.0037 (6) | −0.0015 (6) |
C5B | 0.0199 (7) | 0.0226 (7) | 0.0201 (7) | −0.0010 (6) | 0.0011 (5) | 0.0007 (6) |
C6B | 0.0195 (7) | 0.0222 (7) | 0.0224 (7) | −0.0029 (6) | 0.0013 (6) | 0.0006 (6) |
O1C | 0.0330 (7) | 0.0508 (8) | 0.0523 (8) | 0.0039 (6) | −0.0072 (6) | 0.0256 (7) |
O2C | 0.0337 (7) | 0.0504 (8) | 0.0702 (10) | 0.0179 (6) | 0.0259 (7) | 0.0294 (7) |
O3C | 0.0223 (5) | 0.0256 (6) | 0.0351 (6) | 0.0003 (4) | 0.0075 (5) | 0.0091 (5) |
O4C | 0.0440 (7) | 0.0218 (6) | 0.0542 (8) | 0.0026 (5) | 0.0191 (6) | 0.0055 (5) |
O5C | 0.0311 (7) | 0.0484 (8) | 0.0668 (10) | 0.0159 (6) | 0.0038 (6) | 0.0232 (7) |
O6C | 0.0219 (6) | 0.0472 (7) | 0.0388 (7) | −0.0020 (5) | 0.0091 (5) | 0.0035 (6) |
O7C | 0.0344 (7) | 0.0417 (7) | 0.0449 (7) | −0.0061 (5) | 0.0092 (6) | 0.0163 (6) |
N1C | 0.0206 (7) | 0.0277 (7) | 0.0439 (8) | −0.0014 (5) | 0.0019 (6) | 0.0150 (6) |
N2C | 0.0305 (8) | 0.0259 (7) | 0.0371 (8) | 0.0084 (6) | 0.0140 (6) | 0.0057 (6) |
N3C | 0.0249 (7) | 0.0363 (8) | 0.0253 (7) | −0.0066 (6) | 0.0051 (5) | 0.0024 (6) |
C1C | 0.0250 (8) | 0.0239 (7) | 0.0219 (7) | −0.0031 (6) | 0.0010 (6) | 0.0031 (6) |
C2C | 0.0202 (7) | 0.0249 (8) | 0.0236 (7) | −0.0009 (6) | 0.0004 (6) | 0.0019 (6) |
C3C | 0.0213 (7) | 0.0227 (7) | 0.0213 (7) | −0.0017 (6) | 0.0022 (6) | 0.0017 (6) |
C4C | 0.0267 (8) | 0.0215 (7) | 0.0249 (8) | 0.0021 (6) | 0.0038 (6) | 0.0015 (6) |
C5C | 0.0215 (7) | 0.0290 (8) | 0.0267 (8) | 0.0024 (6) | 0.0057 (6) | −0.0011 (6) |
C6C | 0.0222 (8) | 0.0288 (8) | 0.0218 (7) | −0.0051 (6) | 0.0054 (6) | 0.0000 (6) |
O1D | 0.0514 (9) | 0.0660 (11) | 0.1123 (15) | −0.0325 (8) | 0.0321 (10) | −0.0561 (11) |
O2D | 0.0426 (8) | 0.0415 (8) | 0.0634 (10) | −0.0059 (6) | 0.0214 (7) | −0.0024 (7) |
O3D | 0.0250 (6) | 0.0276 (6) | 0.0445 (7) | −0.0016 (5) | 0.0075 (5) | −0.0118 (5) |
O4D | 0.0878 (13) | 0.0257 (7) | 0.1225 (16) | −0.0057 (8) | 0.0709 (12) | −0.0080 (8) |
O5D | 0.038 (2) | 0.045 (2) | 0.141 (16) | −0.0225 (16) | 0.015 (4) | −0.031 (5) |
O5DA | 0.045 (2) | 0.035 (2) | 0.075 (7) | −0.0157 (16) | 0.025 (3) | −0.008 (3) |
O6D | 0.0262 (6) | 0.0556 (8) | 0.0445 (8) | −0.0018 (6) | 0.0111 (5) | −0.0065 (6) |
O7D | 0.0333 (7) | 0.0399 (7) | 0.0446 (7) | 0.0085 (5) | 0.0031 (5) | −0.0130 (6) |
N1D | 0.0243 (7) | 0.0248 (7) | 0.0523 (9) | −0.0015 (5) | 0.0087 (6) | −0.0080 (6) |
N2D | 0.0384 (9) | 0.0290 (8) | 0.0369 (8) | −0.0069 (6) | 0.0062 (7) | −0.0043 (6) |
N3D | 0.0245 (7) | 0.0423 (9) | 0.0260 (7) | 0.0038 (6) | 0.0007 (5) | −0.0049 (6) |
C1D | 0.0253 (8) | 0.0242 (8) | 0.0280 (8) | 0.0015 (6) | −0.0001 (6) | −0.0052 (6) |
C2D | 0.0211 (7) | 0.0244 (8) | 0.0283 (8) | −0.0016 (6) | 0.0015 (6) | −0.0022 (6) |
C3D | 0.0211 (7) | 0.0251 (8) | 0.0246 (8) | 0.0003 (6) | −0.0004 (6) | −0.0040 (6) |
C4D | 0.0271 (8) | 0.0264 (8) | 0.0238 (8) | −0.0030 (6) | 0.0000 (6) | −0.0025 (6) |
C5D | 0.0220 (8) | 0.0343 (9) | 0.0252 (8) | −0.0041 (6) | 0.0025 (6) | −0.0005 (6) |
C6D | 0.0227 (8) | 0.0334 (9) | 0.0237 (8) | 0.0028 (6) | 0.0020 (6) | −0.0027 (6) |
O1E | 0.0381 (8) | 0.0269 (7) | 0.0914 (12) | 0.0065 (5) | 0.0036 (7) | 0.0034 (7) |
O2E | 0.0224 (6) | 0.0378 (7) | 0.0552 (8) | −0.0012 (5) | −0.0018 (5) | 0.0052 (6) |
O3E | 0.0225 (6) | 0.0262 (6) | 0.0341 (6) | −0.0002 (4) | 0.0068 (5) | 0.0058 (5) |
O4E | 0.0464 (8) | 0.0228 (6) | 0.0692 (10) | −0.0008 (6) | 0.0221 (7) | −0.0001 (6) |
O5E | 0.0317 (7) | 0.0446 (8) | 0.0922 (12) | 0.0163 (6) | 0.0089 (7) | 0.0199 (8) |
O6E | 0.0254 (7) | 0.0687 (9) | 0.0358 (7) | −0.0100 (6) | 0.0100 (5) | 0.0017 (6) |
O7E | 0.0402 (7) | 0.0501 (8) | 0.0457 (8) | −0.0185 (6) | −0.0040 (6) | 0.0210 (7) |
N1E | 0.0236 (7) | 0.0273 (7) | 0.0315 (7) | −0.0001 (5) | 0.0020 (5) | 0.0073 (6) |
N2E | 0.0322 (8) | 0.0280 (7) | 0.0449 (9) | 0.0089 (6) | 0.0164 (7) | 0.0009 (6) |
N3E | 0.0282 (8) | 0.0489 (9) | 0.0234 (7) | −0.0141 (6) | −0.0014 (6) | 0.0073 (6) |
C1E | 0.0277 (8) | 0.0277 (8) | 0.0222 (8) | −0.0055 (6) | −0.0019 (6) | 0.0045 (6) |
C2E | 0.0203 (7) | 0.0263 (8) | 0.0240 (7) | −0.0010 (6) | 0.0003 (6) | 0.0008 (6) |
C3E | 0.0219 (7) | 0.0227 (7) | 0.0219 (7) | −0.0018 (6) | 0.0022 (6) | −0.0019 (6) |
C4E | 0.0247 (8) | 0.0240 (8) | 0.0266 (8) | 0.0001 (6) | 0.0060 (6) | −0.0009 (6) |
C5E | 0.0208 (7) | 0.0341 (9) | 0.0251 (8) | −0.0004 (6) | 0.0051 (6) | −0.0037 (6) |
C6E | 0.0239 (8) | 0.0365 (9) | 0.0206 (7) | −0.0096 (6) | 0.0017 (6) | 0.0015 (6) |
N4A | 0.0278 (7) | 0.0204 (7) | 0.0421 (8) | 0.0044 (5) | −0.0006 (6) | 0.0008 (6) |
N5A | 0.0233 (6) | 0.0186 (6) | 0.0311 (7) | 0.0019 (5) | 0.0003 (5) | 0.0001 (5) |
N6A | 0.0192 (7) | 0.0209 (7) | 0.0364 (8) | 0.0005 (5) | 0.0060 (6) | 0.0041 (6) |
C7A | 0.0299 (9) | 0.0250 (8) | 0.0333 (9) | 0.0003 (6) | 0.0009 (7) | 0.0036 (7) |
C8A | 0.0236 (8) | 0.0211 (8) | 0.0384 (9) | 0.0033 (6) | 0.0039 (7) | −0.0018 (6) |
C9A | 0.0251 (8) | 0.0263 (8) | 0.0325 (9) | 0.0042 (6) | 0.0041 (6) | −0.0012 (7) |
C10A | 0.0293 (8) | 0.0214 (8) | 0.0337 (9) | 0.0026 (6) | −0.0021 (7) | 0.0042 (6) |
C11A | 0.0240 (8) | 0.0193 (7) | 0.0382 (9) | 0.0031 (6) | 0.0035 (7) | 0.0011 (6) |
C12A | 0.0243 (8) | 0.0225 (8) | 0.0372 (9) | 0.0026 (6) | 0.0080 (7) | −0.0010 (7) |
N4B | 0.0290 (7) | 0.0199 (7) | 0.0516 (9) | −0.0043 (5) | −0.0009 (6) | 0.0004 (6) |
N5B | 0.0234 (7) | 0.0219 (6) | 0.0294 (7) | −0.0031 (5) | −0.0003 (5) | 0.0008 (5) |
N6B | 0.0204 (7) | 0.0190 (6) | 0.0347 (8) | −0.0027 (5) | 0.0064 (6) | −0.0037 (5) |
C7B | 0.0298 (9) | 0.0260 (8) | 0.0352 (9) | 0.0004 (6) | −0.0003 (7) | −0.0016 (7) |
C8B | 0.0253 (8) | 0.0244 (8) | 0.0435 (10) | −0.0037 (6) | 0.0058 (7) | 0.0037 (7) |
C9B | 0.0238 (8) | 0.0267 (8) | 0.0338 (9) | −0.0033 (6) | 0.0027 (6) | −0.0003 (7) |
C10B | 0.0299 (8) | 0.0268 (8) | 0.0294 (8) | −0.0037 (6) | −0.0009 (6) | −0.0042 (7) |
C11B | 0.0252 (8) | 0.0204 (7) | 0.0343 (9) | −0.0044 (6) | 0.0048 (6) | −0.0029 (6) |
C12B | 0.0248 (8) | 0.0238 (8) | 0.0329 (8) | −0.0039 (6) | 0.0078 (6) | 0.0002 (6) |
N4C | 0.0319 (8) | 0.0211 (7) | 0.0462 (9) | 0.0051 (6) | −0.0016 (6) | −0.0013 (6) |
N5C | 0.0248 (7) | 0.0193 (6) | 0.0353 (7) | 0.0032 (5) | −0.0013 (5) | −0.0022 (5) |
N6C | 0.0186 (7) | 0.0226 (7) | 0.0304 (7) | 0.0003 (5) | 0.0034 (5) | 0.0042 (5) |
C7C | 0.0349 (9) | 0.0269 (8) | 0.0358 (9) | 0.0014 (7) | 0.0013 (7) | 0.0009 (7) |
C8C | 0.0284 (8) | 0.0283 (8) | 0.0363 (9) | 0.0061 (7) | 0.0026 (7) | −0.0032 (7) |
C9C | 0.0264 (8) | 0.0210 (8) | 0.0433 (10) | 0.0021 (6) | 0.0020 (7) | −0.0036 (7) |
C10C | 0.0299 (8) | 0.0232 (8) | 0.0358 (9) | 0.0019 (6) | −0.0047 (7) | 0.0017 (7) |
C11C | 0.0226 (8) | 0.0206 (8) | 0.0399 (9) | 0.0035 (6) | 0.0002 (7) | −0.0001 (7) |
C12C | 0.0248 (8) | 0.0250 (8) | 0.0325 (8) | 0.0034 (6) | 0.0047 (6) | −0.0012 (6) |
N4D | 0.0304 (7) | 0.0217 (7) | 0.0421 (8) | 0.0027 (5) | −0.0029 (6) | −0.0012 (6) |
N5D | 0.0236 (7) | 0.0222 (7) | 0.0309 (7) | 0.0034 (5) | −0.0024 (5) | −0.0023 (5) |
N6D | 0.0218 (7) | 0.0198 (7) | 0.0290 (7) | 0.0016 (5) | 0.0049 (5) | 0.0026 (5) |
C7D | 0.0245 (8) | 0.0292 (8) | 0.0355 (9) | 0.0028 (6) | 0.0018 (7) | −0.0033 (7) |
C8D | 0.0231 (8) | 0.0232 (8) | 0.0369 (9) | 0.0029 (6) | 0.0020 (6) | −0.0048 (7) |
C9D | 0.0315 (9) | 0.0294 (9) | 0.0342 (9) | −0.0021 (7) | 0.0017 (7) | −0.0004 (7) |
C10D | 0.0286 (8) | 0.0279 (8) | 0.0294 (8) | 0.0044 (6) | −0.0036 (6) | 0.0012 (7) |
C11D | 0.0258 (8) | 0.0236 (8) | 0.0316 (8) | 0.0056 (6) | −0.0009 (6) | 0.0014 (6) |
C12D | 0.0258 (8) | 0.0275 (8) | 0.0317 (8) | 0.0036 (6) | 0.0051 (6) | −0.0048 (7) |
N4E | 0.0329 (8) | 0.0224 (7) | 0.0462 (9) | 0.0037 (6) | −0.0022 (6) | 0.0007 (6) |
N5E | 0.0263 (7) | 0.0217 (6) | 0.0307 (7) | 0.0037 (5) | −0.0018 (5) | −0.0007 (5) |
N6E | 0.0218 (7) | 0.0200 (7) | 0.0319 (8) | 0.0015 (5) | 0.0056 (6) | 0.0022 (5) |
C7E | 0.0328 (9) | 0.0277 (8) | 0.0395 (10) | 0.0000 (7) | 0.0014 (7) | 0.0027 (7) |
C8E | 0.0286 (9) | 0.0238 (8) | 0.0400 (10) | 0.0042 (6) | 0.0027 (7) | −0.0040 (7) |
C9E | 0.0251 (8) | 0.0305 (9) | 0.0386 (9) | 0.0033 (7) | 0.0025 (7) | −0.0006 (7) |
C10E | 0.0345 (9) | 0.0277 (8) | 0.0295 (9) | 0.0030 (7) | −0.0049 (7) | 0.0038 (7) |
C11E | 0.0286 (9) | 0.0232 (8) | 0.0346 (9) | 0.0043 (6) | −0.0008 (7) | 0.0027 (7) |
C12E | 0.0280 (8) | 0.0273 (8) | 0.0307 (9) | 0.0032 (6) | 0.0056 (7) | −0.0030 (7) |
O1A—N1A | 1.227 (2) | N6A—H6AC | 0.95 (2) |
O2A—N1A | 1.224 (2) | N6A—C12A | 1.485 (2) |
O3A—C3A | 1.2448 (18) | C7A—H7A | 0.9500 |
O4A—N2A | 1.2268 (19) | C7A—C9A | 1.359 (2) |
O5A—N2A | 1.2139 (19) | C8A—H8A | 0.9500 |
O6A—N3A | 1.2322 (19) | C9A—H9A | 0.9500 |
O7A—N3A | 1.223 (2) | C10A—H10A | 0.9900 |
N1A—C2A | 1.459 (2) | C10A—H10B | 0.9900 |
N2A—C4A | 1.449 (2) | C10A—C11A | 1.525 (2) |
N3A—C6A | 1.449 (2) | C11A—H11A | 0.9900 |
C1A—H1A | 0.9500 | C11A—H11B | 0.9900 |
C1A—C2A | 1.373 (2) | C11A—C12A | 1.521 (2) |
C1A—C6A | 1.396 (2) | C12A—H12A | 0.9900 |
C2A—C3A | 1.452 (2) | C12A—H12B | 0.9900 |
C3A—C4A | 1.453 (2) | N4B—C7B | 1.367 (2) |
C4A—C5A | 1.376 (2) | N4B—C8B | 1.316 (2) |
C5A—H5A | 0.9500 | N5B—C8B | 1.348 (2) |
C5A—C6A | 1.376 (2) | N5B—C9B | 1.371 (2) |
O1B—N3B | 1.2231 (17) | N5B—C10B | 1.462 (2) |
O2B—N3B | 1.2270 (17) | N6B—H6BA | 0.92 (2) |
O3B—C5B | 1.2451 (18) | N6B—H6BB | 0.89 (2) |
O4B—N2B | 1.225 (2) | N6B—H6BC | 0.92 (2) |
O5B—N2B | 1.2291 (19) | N6B—C12B | 1.487 (2) |
O6B—N1B | 1.2295 (19) | C7B—H7B | 0.9500 |
O7B—N1B | 1.2298 (19) | C7B—C9B | 1.355 (2) |
N1B—C2B | 1.447 (2) | C8B—H8B | 0.9500 |
N2B—C4B | 1.453 (2) | C9B—H9B | 0.9500 |
N3B—C6B | 1.4567 (18) | C10B—H10C | 0.9900 |
C1B—H1B | 0.9500 | C10B—H10D | 0.9900 |
C1B—C2B | 1.391 (2) | C10B—C11B | 1.526 (2) |
C1B—C6B | 1.371 (2) | C11B—H11C | 0.9900 |
C2B—C3B | 1.380 (2) | C11B—H11D | 0.9900 |
C3B—H3B | 0.9500 | C11B—C12B | 1.520 (2) |
C3B—C4B | 1.371 (2) | C12B—H12C | 0.9900 |
C4B—C5B | 1.452 (2) | C12B—H12D | 0.9900 |
C5B—C6B | 1.451 (2) | N4C—C7C | 1.375 (2) |
O1C—N1C | 1.2267 (18) | N4C—C9C | 1.315 (2) |
O2C—N1C | 1.2206 (19) | N5C—C8C | 1.372 (2) |
O3C—C3C | 1.2492 (18) | N5C—C9C | 1.348 (2) |
O4C—N2C | 1.2238 (18) | N5C—C10C | 1.461 (2) |
O5C—N2C | 1.235 (2) | N6C—H6CA | 0.85 (2) |
O6C—N3C | 1.2329 (18) | N6C—H6CB | 0.89 (2) |
O7C—N3C | 1.2273 (19) | N6C—H6CC | 0.92 (2) |
N1C—C2C | 1.4523 (19) | N6C—C12C | 1.484 (2) |
N2C—C4C | 1.446 (2) | C7C—H7C | 0.9500 |
N3C—C6C | 1.4474 (19) | C7C—C8C | 1.356 (2) |
C1C—H1C | 0.9500 | C8C—H8C | 0.9500 |
C1C—C2C | 1.377 (2) | C9C—H9C | 0.9500 |
C1C—C6C | 1.387 (2) | C10C—H10E | 0.9900 |
C2C—C3C | 1.448 (2) | C10C—H10F | 0.9900 |
C3C—C4C | 1.450 (2) | C10C—C11C | 1.525 (2) |
C4C—C5C | 1.375 (2) | C11C—H11E | 0.9900 |
C5C—H5C | 0.9500 | C11C—H11F | 0.9900 |
C5C—C6C | 1.372 (2) | C11C—C12C | 1.520 (2) |
O1D—N1D | 1.201 (2) | C12C—H12E | 0.9900 |
O2D—N1D | 1.229 (2) | C12C—H12F | 0.9900 |
O3D—C3D | 1.2469 (18) | N4D—C8D | 1.315 (2) |
O4D—N2D | 1.198 (2) | N4D—C9D | 1.373 (2) |
O5D—N2D | 1.172 (6) | N5D—C7D | 1.373 (2) |
O5DA—N2D | 1.284 (6) | N5D—C8D | 1.3493 (19) |
O6D—N3D | 1.2288 (19) | N5D—C10D | 1.465 (2) |
O7D—N3D | 1.2276 (19) | N6D—H6DA | 0.89 (2) |
N1D—C2D | 1.457 (2) | N6D—H6DB | 0.89 (2) |
N2D—C4D | 1.451 (2) | N6D—H6DC | 0.89 (2) |
N3D—C6D | 1.452 (2) | N6D—C12D | 1.482 (2) |
C1D—H1D | 0.9500 | C7D—H7D | 0.9500 |
C1D—C2D | 1.372 (2) | C7D—C9D | 1.353 (2) |
C1D—C6D | 1.395 (2) | C8D—H8D | 0.9500 |
C2D—C3D | 1.450 (2) | C9D—H9D | 0.9500 |
C3D—C4D | 1.456 (2) | C10D—H10G | 0.9900 |
C4D—C5D | 1.378 (2) | C10D—H10H | 0.9900 |
C5D—H5D | 0.9500 | C10D—C11D | 1.524 (2) |
C5D—C6D | 1.374 (2) | C11D—H11G | 0.9900 |
O1E—N1E | 1.2253 (18) | C11D—H11H | 0.9900 |
O2E—N1E | 1.2249 (18) | C11D—C12D | 1.517 (2) |
O3E—C3E | 1.2472 (18) | C12D—H12G | 0.9900 |
O4E—N2E | 1.2234 (19) | C12D—H12H | 0.9900 |
O5E—N2E | 1.233 (2) | N4E—C7E | 1.369 (2) |
O6E—N3E | 1.228 (2) | N4E—C8E | 1.317 (2) |
O7E—N3E | 1.232 (2) | N5E—C8E | 1.347 (2) |
N1E—C2E | 1.4546 (19) | N5E—C9E | 1.372 (2) |
N2E—C4E | 1.448 (2) | N5E—C10E | 1.464 (2) |
N3E—C6E | 1.448 (2) | N6E—H6EA | 0.91 (2) |
C1E—H1E | 0.9500 | N6E—H6EB | 0.87 (2) |
C1E—C2E | 1.373 (2) | N6E—H6EC | 0.93 (2) |
C1E—C6E | 1.385 (2) | N6E—C12E | 1.483 (2) |
C2E—C3E | 1.452 (2) | C7E—H7E | 0.9500 |
C3E—C4E | 1.453 (2) | C7E—C9E | 1.353 (2) |
C4E—C5E | 1.370 (2) | C8E—H8E | 0.9500 |
C5E—H5E | 0.9500 | C9E—H9E | 0.9500 |
C5E—C6E | 1.380 (2) | C10E—H10I | 0.9900 |
N4A—C7A | 1.372 (2) | C10E—H10J | 0.9900 |
N4A—C8A | 1.316 (2) | C10E—C11E | 1.526 (2) |
N5A—C8A | 1.3485 (19) | C11E—H11I | 0.9900 |
N5A—C9A | 1.374 (2) | C11E—H11J | 0.9900 |
N5A—C10A | 1.4645 (19) | C11E—C12E | 1.517 (2) |
N6A—H6AA | 0.85 (2) | C12E—H12I | 0.9900 |
N6A—H6AB | 0.91 (2) | C12E—H12J | 0.9900 |
O1A—N1A—C2A | 117.71 (14) | C11A—C10A—H10B | 109.2 |
O2A—N1A—O1A | 123.60 (15) | C10A—C11A—H11A | 109.3 |
O2A—N1A—C2A | 118.68 (14) | C10A—C11A—H11B | 109.3 |
O4A—N2A—C4A | 119.55 (14) | H11A—C11A—H11B | 107.9 |
O5A—N2A—O4A | 121.60 (15) | C12A—C11A—C10A | 111.75 (13) |
O5A—N2A—C4A | 118.85 (15) | C12A—C11A—H11A | 109.3 |
O6A—N3A—C6A | 117.84 (15) | C12A—C11A—H11B | 109.3 |
O7A—N3A—O6A | 123.80 (14) | N6A—C12A—C11A | 111.71 (13) |
O7A—N3A—C6A | 118.35 (14) | N6A—C12A—H12A | 109.3 |
C2A—C1A—H1A | 120.6 | N6A—C12A—H12B | 109.3 |
C2A—C1A—C6A | 118.77 (15) | C11A—C12A—H12A | 109.3 |
C6A—C1A—H1A | 120.6 | C11A—C12A—H12B | 109.3 |
C1A—C2A—N1A | 116.22 (14) | H12A—C12A—H12B | 107.9 |
C1A—C2A—C3A | 124.90 (14) | C8B—N4B—C7B | 105.42 (14) |
C3A—C2A—N1A | 118.87 (13) | C8B—N5B—C9B | 106.63 (13) |
O3A—C3A—C2A | 124.92 (14) | C8B—N5B—C10B | 127.79 (14) |
O3A—C3A—C4A | 124.07 (14) | C9B—N5B—C10B | 125.57 (13) |
C2A—C3A—C4A | 111.01 (13) | H6BA—N6B—H6BB | 110.2 (17) |
N2A—C4A—C3A | 119.08 (14) | H6BA—N6B—H6BC | 108.0 (16) |
C5A—C4A—N2A | 116.44 (14) | H6BB—N6B—H6BC | 108.1 (17) |
C5A—C4A—C3A | 124.48 (14) | C12B—N6B—H6BA | 111.4 (11) |
C4A—C5A—H5A | 120.3 | C12B—N6B—H6BB | 108.3 (13) |
C6A—C5A—C4A | 119.37 (14) | C12B—N6B—H6BC | 110.8 (12) |
C6A—C5A—H5A | 120.3 | N4B—C7B—H7B | 125.0 |
C1A—C6A—N3A | 118.97 (15) | C9B—C7B—N4B | 110.00 (15) |
C5A—C6A—N3A | 120.01 (14) | C9B—C7B—H7B | 125.0 |
C5A—C6A—C1A | 121.00 (14) | N4B—C8B—N5B | 111.75 (15) |
O6B—N1B—O7B | 123.70 (14) | N4B—C8B—H8B | 124.1 |
O6B—N1B—C2B | 118.19 (14) | N5B—C8B—H8B | 124.1 |
O7B—N1B—C2B | 118.11 (14) | N5B—C9B—H9B | 126.9 |
O4B—N2B—O5B | 123.03 (15) | C7B—C9B—N5B | 106.18 (14) |
O4B—N2B—C4B | 119.13 (14) | C7B—C9B—H9B | 126.9 |
O5B—N2B—C4B | 117.83 (15) | N5B—C10B—H10C | 109.2 |
O1B—N3B—O2B | 123.41 (13) | N5B—C10B—H10D | 109.2 |
O1B—N3B—C6B | 118.79 (13) | N5B—C10B—C11B | 112.23 (13) |
O2B—N3B—C6B | 117.72 (13) | H10C—C10B—H10D | 107.9 |
C2B—C1B—H1B | 120.6 | C11B—C10B—H10C | 109.2 |
C6B—C1B—H1B | 120.6 | C11B—C10B—H10D | 109.2 |
C6B—C1B—C2B | 118.72 (14) | C10B—C11B—H11C | 109.3 |
C1B—C2B—N1B | 120.21 (15) | C10B—C11B—H11D | 109.3 |
C3B—C2B—N1B | 118.68 (14) | H11C—C11B—H11D | 107.9 |
C3B—C2B—C1B | 121.07 (14) | C12B—C11B—C10B | 111.74 (13) |
C2B—C3B—H3B | 120.3 | C12B—C11B—H11C | 109.3 |
C4B—C3B—C2B | 119.38 (14) | C12B—C11B—H11D | 109.3 |
C4B—C3B—H3B | 120.3 | N6B—C12B—C11B | 112.16 (13) |
C3B—C4B—N2B | 115.98 (14) | N6B—C12B—H12C | 109.2 |
C3B—C4B—C5B | 124.57 (14) | N6B—C12B—H12D | 109.2 |
C5B—C4B—N2B | 119.45 (14) | C11B—C12B—H12C | 109.2 |
O3B—C5B—C4B | 124.26 (14) | C11B—C12B—H12D | 109.2 |
O3B—C5B—C6B | 124.58 (13) | H12C—C12B—H12D | 107.9 |
C6B—C5B—C4B | 110.99 (13) | C9C—N4C—C7C | 105.23 (14) |
C1B—C6B—N3B | 116.43 (13) | C8C—N5C—C10C | 126.59 (14) |
C1B—C6B—C5B | 125.00 (14) | C9C—N5C—C8C | 106.65 (14) |
C5B—C6B—N3B | 118.57 (13) | C9C—N5C—C10C | 126.75 (15) |
O1C—N1C—C2C | 118.16 (14) | H6CA—N6C—H6CB | 109.2 (17) |
O2C—N1C—O1C | 123.32 (14) | H6CA—N6C—H6CC | 109.4 (17) |
O2C—N1C—C2C | 118.50 (14) | H6CB—N6C—H6CC | 106.2 (16) |
O4C—N2C—O5C | 123.11 (14) | C12C—N6C—H6CA | 109.0 (12) |
O4C—N2C—C4C | 119.00 (14) | C12C—N6C—H6CB | 111.9 (12) |
O5C—N2C—C4C | 117.88 (14) | C12C—N6C—H6CC | 111.1 (12) |
O6C—N3C—C6C | 117.94 (14) | N4C—C7C—H7C | 125.1 |
O7C—N3C—O6C | 123.59 (13) | C8C—C7C—N4C | 109.87 (16) |
O7C—N3C—C6C | 118.46 (14) | C8C—C7C—H7C | 125.1 |
C2C—C1C—H1C | 120.6 | N5C—C8C—H8C | 126.9 |
C2C—C1C—C6C | 118.77 (14) | C7C—C8C—N5C | 106.29 (15) |
C6C—C1C—H1C | 120.6 | C7C—C8C—H8C | 126.9 |
C1C—C2C—N1C | 115.76 (13) | N4C—C9C—N5C | 111.97 (15) |
C1C—C2C—C3C | 125.07 (14) | N4C—C9C—H9C | 124.0 |
C3C—C2C—N1C | 119.16 (13) | N5C—C9C—H9C | 124.0 |
O3C—C3C—C2C | 125.04 (14) | N5C—C10C—H10E | 109.1 |
O3C—C3C—C4C | 124.28 (14) | N5C—C10C—H10F | 109.1 |
C2C—C3C—C4C | 110.67 (13) | N5C—C10C—C11C | 112.30 (14) |
N2C—C4C—C3C | 119.42 (13) | H10E—C10C—H10F | 107.9 |
C5C—C4C—N2C | 115.46 (14) | C11C—C10C—H10E | 109.1 |
C5C—C4C—C3C | 125.02 (14) | C11C—C10C—H10F | 109.1 |
C4C—C5C—H5C | 120.4 | C10C—C11C—H11E | 109.3 |
C6C—C5C—C4C | 119.16 (14) | C10C—C11C—H11F | 109.3 |
C6C—C5C—H5C | 120.4 | H11E—C11C—H11F | 108.0 |
C1C—C6C—N3C | 119.58 (14) | C12C—C11C—C10C | 111.63 (13) |
C5C—C6C—N3C | 119.24 (14) | C12C—C11C—H11E | 109.3 |
C5C—C6C—C1C | 121.18 (14) | C12C—C11C—H11F | 109.3 |
O1D—N1D—O2D | 123.01 (16) | N6C—C12C—C11C | 111.62 (13) |
O1D—N1D—C2D | 118.78 (15) | N6C—C12C—H12E | 109.3 |
O2D—N1D—C2D | 118.13 (14) | N6C—C12C—H12F | 109.3 |
O4D—N2D—O5DA | 121.1 (4) | C11C—C12C—H12E | 109.3 |
O4D—N2D—C4D | 121.11 (15) | C11C—C12C—H12F | 109.3 |
O5D—N2D—O4D | 116.2 (6) | H12E—C12C—H12F | 108.0 |
O5D—N2D—C4D | 120.7 (4) | C8D—N4D—C9D | 105.07 (14) |
O5DA—N2D—C4D | 114.8 (6) | C7D—N5D—C10D | 126.36 (13) |
O6D—N3D—C6D | 117.99 (15) | C8D—N5D—C7D | 106.60 (14) |
O7D—N3D—O6D | 123.75 (14) | C8D—N5D—C10D | 126.98 (14) |
O7D—N3D—C6D | 118.26 (14) | H6DA—N6D—H6DB | 110.1 (17) |
C2D—C1D—H1D | 120.7 | H6DA—N6D—H6DC | 106.3 (16) |
C2D—C1D—C6D | 118.59 (15) | H6DB—N6D—H6DC | 109.1 (17) |
C6D—C1D—H1D | 120.7 | C12D—N6D—H6DA | 110.3 (12) |
C1D—C2D—N1D | 116.12 (14) | C12D—N6D—H6DB | 109.7 (13) |
C1D—C2D—C3D | 125.24 (14) | C12D—N6D—H6DC | 111.3 (12) |
C3D—C2D—N1D | 118.64 (13) | N5D—C7D—H7D | 127.0 |
O3D—C3D—C2D | 123.99 (14) | C9D—C7D—N5D | 106.10 (14) |
O3D—C3D—C4D | 124.81 (14) | C9D—C7D—H7D | 127.0 |
C2D—C3D—C4D | 111.19 (13) | N4D—C8D—N5D | 111.99 (15) |
N2D—C4D—C3D | 120.05 (14) | N4D—C8D—H8D | 124.0 |
C5D—C4D—N2D | 116.02 (14) | N5D—C8D—H8D | 124.0 |
C5D—C4D—C3D | 123.92 (15) | N4D—C9D—H9D | 124.9 |
C4D—C5D—H5D | 120.0 | C7D—C9D—N4D | 110.24 (15) |
C6D—C5D—C4D | 119.94 (15) | C7D—C9D—H9D | 124.9 |
C6D—C5D—H5D | 120.0 | N5D—C10D—H10G | 109.2 |
C1D—C6D—N3D | 119.68 (15) | N5D—C10D—H10H | 109.2 |
C5D—C6D—N3D | 119.38 (14) | N5D—C10D—C11D | 112.06 (13) |
C5D—C6D—C1D | 120.93 (15) | H10G—C10D—H10H | 107.9 |
O1E—N1E—C2E | 118.81 (13) | C11D—C10D—H10G | 109.2 |
O2E—N1E—O1E | 123.10 (14) | C11D—C10D—H10H | 109.2 |
O2E—N1E—C2E | 118.02 (13) | C10D—C11D—H11G | 109.3 |
O4E—N2E—O5E | 122.89 (15) | C10D—C11D—H11H | 109.3 |
O4E—N2E—C4E | 119.37 (15) | H11G—C11D—H11H | 108.0 |
O5E—N2E—C4E | 117.74 (15) | C12D—C11D—C10D | 111.64 (13) |
O6E—N3E—O7E | 123.84 (15) | C12D—C11D—H11G | 109.3 |
O6E—N3E—C6E | 118.14 (15) | C12D—C11D—H11H | 109.3 |
O7E—N3E—C6E | 118.01 (15) | N6D—C12D—C11D | 113.07 (13) |
C2E—C1E—H1E | 120.6 | N6D—C12D—H12G | 109.0 |
C2E—C1E—C6E | 118.78 (15) | N6D—C12D—H12H | 109.0 |
C6E—C1E—H1E | 120.6 | C11D—C12D—H12G | 109.0 |
C1E—C2E—N1E | 116.32 (14) | C11D—C12D—H12H | 109.0 |
C1E—C2E—C3E | 124.94 (14) | H12G—C12D—H12H | 107.8 |
C3E—C2E—N1E | 118.74 (13) | C8E—N4E—C7E | 105.39 (14) |
O3E—C3E—C2E | 124.73 (14) | C8E—N5E—C9E | 106.80 (14) |
O3E—C3E—C4E | 124.29 (14) | C8E—N5E—C10E | 127.40 (15) |
C2E—C3E—C4E | 110.81 (13) | C9E—N5E—C10E | 125.74 (14) |
N2E—C4E—C3E | 119.12 (13) | H6EA—N6E—H6EB | 109.0 (18) |
C5E—C4E—N2E | 115.91 (14) | H6EA—N6E—H6EC | 105.3 (17) |
C5E—C4E—C3E | 124.92 (15) | H6EB—N6E—H6EC | 110.5 (17) |
C4E—C5E—H5E | 120.5 | C12E—N6E—H6EA | 111.4 (13) |
C4E—C5E—C6E | 119.08 (15) | C12E—N6E—H6EB | 109.5 (13) |
C6E—C5E—H5E | 120.5 | C12E—N6E—H6EC | 111.0 (13) |
C1E—C6E—N3E | 120.04 (15) | N4E—C7E—H7E | 124.9 |
C5E—C6E—N3E | 118.65 (15) | C9E—C7E—N4E | 110.10 (16) |
C5E—C6E—C1E | 121.31 (14) | C9E—C7E—H7E | 124.9 |
C8A—N4A—C7A | 105.28 (13) | N4E—C8E—N5E | 111.62 (15) |
C8A—N5A—C9A | 106.91 (13) | N4E—C8E—H8E | 124.2 |
C8A—N5A—C10A | 126.75 (14) | N5E—C8E—H8E | 124.2 |
C9A—N5A—C10A | 126.32 (13) | N5E—C9E—H9E | 127.0 |
H6AA—N6A—H6AB | 110.8 (17) | C7E—C9E—N5E | 106.09 (15) |
H6AA—N6A—H6AC | 109.0 (17) | C7E—C9E—H9E | 127.0 |
H6AB—N6A—H6AC | 108.3 (16) | N5E—C10E—H10I | 109.2 |
C12A—N6A—H6AA | 108.4 (13) | N5E—C10E—H10J | 109.2 |
C12A—N6A—H6AB | 110.0 (12) | N5E—C10E—C11E | 112.11 (13) |
C12A—N6A—H6AC | 110.3 (12) | H10I—C10E—H10J | 107.9 |
N4A—C7A—H7A | 124.9 | C11E—C10E—H10I | 109.2 |
C9A—C7A—N4A | 110.19 (15) | C11E—C10E—H10J | 109.2 |
C9A—C7A—H7A | 124.9 | C10E—C11E—H11I | 109.3 |
N4A—C8A—N5A | 111.82 (14) | C10E—C11E—H11J | 109.3 |
N4A—C8A—H8A | 124.1 | H11I—C11E—H11J | 108.0 |
N5A—C8A—H8A | 124.1 | C12E—C11E—C10E | 111.61 (13) |
N5A—C9A—H9A | 127.1 | C12E—C11E—H11I | 109.3 |
C7A—C9A—N5A | 105.80 (14) | C12E—C11E—H11J | 109.3 |
C7A—C9A—H9A | 127.1 | N6E—C12E—C11E | 112.69 (13) |
N5A—C10A—H10A | 109.2 | N6E—C12E—H12I | 109.1 |
N5A—C10A—H10B | 109.2 | N6E—C12E—H12J | 109.1 |
N5A—C10A—C11A | 112.22 (13) | C11E—C12E—H12I | 109.1 |
H10A—C10A—H10B | 107.9 | C11E—C12E—H12J | 109.1 |
C11A—C10A—H10A | 109.2 | H12I—C12E—H12J | 107.8 |
O1A—N1A—C2A—C1A | 35.4 (2) | O7D—N3D—C6D—C5D | 179.93 (15) |
O1A—N1A—C2A—C3A | −143.82 (17) | N1D—C2D—C3D—O3D | −0.7 (2) |
O2A—N1A—C2A—C1A | −144.20 (17) | N1D—C2D—C3D—C4D | 178.26 (14) |
O2A—N1A—C2A—C3A | 36.5 (2) | N2D—C4D—C5D—C6D | 174.80 (15) |
O3A—C3A—C4A—N2A | 7.5 (2) | C1D—C2D—C3D—O3D | 179.78 (16) |
O3A—C3A—C4A—C5A | −172.60 (15) | C1D—C2D—C3D—C4D | −1.3 (2) |
O4A—N2A—C4A—C3A | 26.1 (2) | C2D—C1D—C6D—N3D | −176.99 (14) |
O4A—N2A—C4A—C5A | −153.79 (16) | C2D—C1D—C6D—C5D | 3.4 (2) |
O5A—N2A—C4A—C3A | −154.60 (17) | C2D—C3D—C4D—N2D | −174.13 (14) |
O5A—N2A—C4A—C5A | 25.5 (2) | C2D—C3D—C4D—C5D | 4.4 (2) |
O6A—N3A—C6A—C1A | −179.68 (14) | C3D—C4D—C5D—C6D | −3.8 (2) |
O6A—N3A—C6A—C5A | −1.3 (2) | C4D—C5D—C6D—N3D | 179.98 (14) |
O7A—N3A—C6A—C1A | 0.9 (2) | C4D—C5D—C6D—C1D | −0.4 (2) |
O7A—N3A—C6A—C5A | 179.23 (15) | C6D—C1D—C2D—N1D | 178.02 (14) |
N1A—C2A—C3A—O3A | −4.7 (2) | C6D—C1D—C2D—C3D | −2.4 (3) |
N1A—C2A—C3A—C4A | 174.90 (14) | O1E—N1E—C2E—C1E | −33.6 (2) |
N2A—C4A—C5A—C6A | 174.32 (14) | O1E—N1E—C2E—C3E | 145.62 (16) |
C1A—C2A—C3A—O3A | 176.05 (16) | O2E—N1E—C2E—C1E | 143.49 (15) |
C1A—C2A—C3A—C4A | −4.3 (2) | O2E—N1E—C2E—C3E | −37.3 (2) |
C2A—C1A—C6A—N3A | −177.65 (14) | O3E—C3E—C4E—N2E | 5.2 (2) |
C2A—C1A—C6A—C5A | 4.0 (2) | O3E—C3E—C4E—C5E | −171.92 (15) |
C2A—C3A—C4A—N2A | −172.17 (14) | O4E—N2E—C4E—C3E | 34.7 (2) |
C2A—C3A—C4A—C5A | 7.7 (2) | O4E—N2E—C4E—C5E | −147.92 (16) |
C3A—C4A—C5A—C6A | −5.6 (2) | O5E—N2E—C4E—C3E | −144.93 (16) |
C4A—C5A—C6A—N3A | −179.10 (14) | O5E—N2E—C4E—C5E | 32.4 (2) |
C4A—C5A—C6A—C1A | −0.8 (2) | O6E—N3E—C6E—C1E | −172.73 (14) |
C6A—C1A—C2A—N1A | 179.61 (14) | O6E—N3E—C6E—C5E | 6.7 (2) |
C6A—C1A—C2A—C3A | −1.2 (2) | O7E—N3E—C6E—C1E | 8.1 (2) |
O1B—N3B—C6B—C1B | −33.8 (2) | O7E—N3E—C6E—C5E | −172.40 (15) |
O1B—N3B—C6B—C5B | 145.57 (15) | N1E—C2E—C3E—O3E | −8.5 (2) |
O2B—N3B—C6B—C1B | 143.09 (15) | N1E—C2E—C3E—C4E | 176.08 (13) |
O2B—N3B—C6B—C5B | −37.5 (2) | N2E—C4E—C5E—C6E | −179.10 (14) |
O3B—C5B—C6B—N3B | −9.6 (2) | C1E—C2E—C3E—O3E | 170.70 (15) |
O3B—C5B—C6B—C1B | 169.72 (15) | C1E—C2E—C3E—C4E | −4.8 (2) |
O4B—N2B—C4B—C3B | −150.42 (15) | C2E—C1E—C6E—N3E | 177.47 (14) |
O4B—N2B—C4B—C5B | 29.8 (2) | C2E—C1E—C6E—C5E | −2.0 (2) |
O5B—N2B—C4B—C3B | 28.9 (2) | C2E—C3E—C4E—N2E | −179.32 (14) |
O5B—N2B—C4B—C5B | −150.98 (15) | C2E—C3E—C4E—C5E | 3.6 (2) |
O6B—N1B—C2B—C1B | −175.70 (14) | C3E—C4E—C5E—C6E | −1.9 (2) |
O6B—N1B—C2B—C3B | 1.8 (2) | C4E—C5E—C6E—N3E | −178.58 (14) |
O7B—N1B—C2B—C1B | 4.4 (2) | C4E—C5E—C6E—C1E | 0.9 (2) |
O7B—N1B—C2B—C3B | −178.12 (14) | C6E—C1E—C2E—N1E | −176.60 (14) |
N1B—C2B—C3B—C4B | −176.94 (14) | C6E—C1E—C2E—C3E | 4.2 (2) |
N2B—C4B—C5B—O3B | 10.0 (2) | N4A—C7A—C9A—N5A | 0.25 (19) |
N2B—C4B—C5B—C6B | −174.48 (14) | N5A—C10A—C11A—C12A | 75.73 (17) |
C1B—C2B—C3B—C4B | 0.5 (2) | C7A—N4A—C8A—N5A | 0.13 (19) |
C2B—C1B—C6B—N3B | −177.07 (13) | C8A—N4A—C7A—C9A | −0.24 (19) |
C2B—C1B—C6B—C5B | 3.6 (2) | C8A—N5A—C9A—C7A | −0.17 (18) |
C2B—C3B—C4B—N2B | 176.73 (14) | C8A—N5A—C10A—C11A | −99.79 (18) |
C2B—C3B—C4B—C5B | −3.5 (2) | C9A—N5A—C8A—N4A | 0.02 (19) |
C3B—C4B—C5B—O3B | −169.83 (15) | C9A—N5A—C10A—C11A | 81.85 (19) |
C3B—C4B—C5B—C6B | 5.7 (2) | C10A—N5A—C8A—N4A | −178.60 (14) |
C4B—C5B—C6B—N3B | 174.87 (13) | C10A—N5A—C9A—C7A | 178.46 (15) |
C4B—C5B—C6B—C1B | −5.8 (2) | C10A—C11A—C12A—N6A | −169.81 (13) |
C6B—C1B—C2B—N1B | 176.85 (13) | N4B—C7B—C9B—N5B | 0.42 (19) |
C6B—C1B—C2B—C3B | −0.6 (2) | N5B—C10B—C11B—C12B | 77.05 (17) |
O1C—N1C—C2C—C1C | −35.9 (2) | C7B—N4B—C8B—N5B | −0.2 (2) |
O1C—N1C—C2C—C3C | 145.17 (15) | C8B—N4B—C7B—C9B | −0.1 (2) |
O2C—N1C—C2C—C1C | 142.27 (16) | C8B—N5B—C9B—C7B | −0.53 (18) |
O2C—N1C—C2C—C3C | −36.7 (2) | C8B—N5B—C10B—C11B | −96.84 (19) |
O3C—C3C—C4C—N2C | −0.5 (2) | C9B—N5B—C8B—N4B | 0.48 (19) |
O3C—C3C—C4C—C5C | 175.73 (15) | C9B—N5B—C10B—C11B | 82.11 (19) |
O4C—N2C—C4C—C3C | −36.2 (2) | C10B—N5B—C8B—N4B | 179.59 (15) |
O4C—N2C—C4C—C5C | 147.29 (15) | C10B—N5B—C9B—C7B | −179.66 (14) |
O5C—N2C—C4C—C3C | 143.12 (16) | C10B—C11B—C12B—N6B | −167.69 (13) |
O5C—N2C—C4C—C5C | −33.4 (2) | N4C—C7C—C8C—N5C | 0.2 (2) |
O6C—N3C—C6C—C1C | 174.06 (14) | N5C—C10C—C11C—C12C | 74.86 (18) |
O6C—N3C—C6C—C5C | −5.9 (2) | C7C—N4C—C9C—N5C | 0.14 (19) |
O7C—N3C—C6C—C1C | −7.1 (2) | C8C—N5C—C9C—N4C | −0.01 (19) |
O7C—N3C—C6C—C5C | 172.89 (15) | C8C—N5C—C10C—C11C | 79.6 (2) |
N1C—C2C—C3C—O3C | 0.4 (2) | C9C—N4C—C7C—C8C | −0.2 (2) |
N1C—C2C—C3C—C4C | 179.80 (13) | C9C—N5C—C8C—C7C | −0.12 (19) |
N2C—C4C—C5C—C6C | 179.99 (14) | C9C—N5C—C10C—C11C | −101.93 (19) |
C1C—C2C—C3C—O3C | −178.42 (15) | C10C—N5C—C8C—C7C | 178.57 (15) |
C1C—C2C—C3C—C4C | 1.0 (2) | C10C—N5C—C9C—N4C | −178.70 (15) |
C2C—C1C—C6C—N3C | 178.18 (14) | C10C—C11C—C12C—N6C | −166.96 (13) |
C2C—C1C—C6C—C5C | −1.8 (2) | N5D—C7D—C9D—N4D | −0.43 (19) |
C2C—C3C—C4C—N2C | −179.86 (14) | N5D—C10D—C11D—C12D | −70.02 (18) |
C2C—C3C—C4C—C5C | −3.7 (2) | C7D—N5D—C8D—N4D | −0.51 (19) |
C3C—C4C—C5C—C6C | 3.7 (2) | C7D—N5D—C10D—C11D | −77.33 (19) |
C4C—C5C—C6C—N3C | 179.33 (14) | C8D—N4D—C9D—C7D | 0.13 (19) |
C4C—C5C—C6C—C1C | −0.7 (2) | C8D—N5D—C7D—C9D | 0.56 (18) |
C6C—C1C—C2C—N1C | −177.26 (14) | C8D—N5D—C10D—C11D | 99.47 (18) |
C6C—C1C—C2C—C3C | 1.6 (2) | C9D—N4D—C8D—N5D | 0.24 (19) |
O1D—N1D—C2D—C1D | 34.2 (2) | C10D—N5D—C7D—C9D | 177.90 (15) |
O1D—N1D—C2D—C3D | −145.42 (19) | C10D—N5D—C8D—N4D | −177.83 (14) |
O2D—N1D—C2D—C1D | −142.63 (16) | C10D—C11D—C12D—N6D | 162.89 (13) |
O2D—N1D—C2D—C3D | 37.8 (2) | N4E—C7E—C9E—N5E | −0.4 (2) |
O3D—C3D—C4D—N2D | 4.8 (2) | N5E—C10E—C11E—C12E | −73.02 (18) |
O3D—C3D—C4D—C5D | −176.62 (16) | C7E—N4E—C8E—N5E | 0.1 (2) |
O4D—N2D—C4D—C3D | 5.9 (3) | C8E—N4E—C7E—C9E | 0.2 (2) |
O4D—N2D—C4D—C5D | −172.77 (19) | C8E—N5E—C9E—C7E | 0.41 (19) |
O5D—N2D—C4D—C3D | −158 (2) | C8E—N5E—C10E—C11E | 95.96 (19) |
O5D—N2D—C4D—C5D | 24 (2) | C9E—N5E—C8E—N4E | −0.3 (2) |
O5DA—N2D—C4D—C3D | 166.4 (11) | C9E—N5E—C10E—C11E | −80.7 (2) |
O5DA—N2D—C4D—C5D | −12.3 (11) | C10E—N5E—C8E—N4E | −177.52 (15) |
O6D—N3D—C6D—C1D | 179.42 (15) | C10E—N5E—C9E—C7E | 177.67 (15) |
O6D—N3D—C6D—C5D | −0.9 (2) | C10E—C11E—C12E—N6E | 165.79 (14) |
O7D—N3D—C6D—C1D | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6A—H6AA···O3Ei | 0.85 (2) | 2.06 (2) | 2.8943 (18) | 167.5 (18) |
N6A—H6AB···O3Dii | 0.91 (2) | 2.08 (2) | 2.8671 (18) | 143.1 (16) |
N6A—H6AB···O4Dii | 0.91 (2) | 2.25 (2) | 2.961 (2) | 134.6 (15) |
N6A—H6AC···N4C | 0.95 (2) | 1.87 (2) | 2.8157 (19) | 172.5 (18) |
N6B—H6BA···O3Biii | 0.92 (2) | 2.117 (19) | 2.8728 (17) | 138.5 (15) |
N6B—H6BA···O4Biii | 0.92 (2) | 2.268 (19) | 3.006 (2) | 136.6 (15) |
N6B—H6BB···O3B | 0.89 (2) | 2.00 (2) | 2.8502 (17) | 161.0 (19) |
N6B—H6BC···N4Aiv | 0.92 (2) | 1.88 (2) | 2.7988 (19) | 173.4 (17) |
N6C—H6CA···O2Cv | 0.85 (2) | 2.305 (18) | 2.8334 (19) | 120.9 (15) |
N6C—H6CA···O3Cv | 0.85 (2) | 2.10 (2) | 2.8944 (18) | 155.4 (17) |
N6C—H6CB···O3Avi | 0.89 (2) | 2.174 (19) | 2.9145 (18) | 140.2 (16) |
N6C—H6CB···O4Avi | 0.89 (2) | 2.270 (19) | 2.986 (2) | 137.3 (15) |
N6C—H6CC···N4Dvi | 0.92 (2) | 1.91 (2) | 2.8179 (19) | 167.6 (17) |
N6D—H6DA···O2Avii | 0.89 (2) | 2.361 (19) | 2.9631 (19) | 124.9 (15) |
N6D—H6DA···O3Avii | 0.89 (2) | 2.06 (2) | 2.8340 (17) | 145.0 (16) |
N6D—H6DB···O3Cvi | 0.89 (2) | 2.16 (2) | 2.9171 (17) | 142.0 (17) |
N6D—H6DB···O4Cvi | 0.89 (2) | 2.27 (2) | 2.9323 (19) | 130.5 (16) |
N6D—H6DC···N4E | 0.89 (2) | 1.91 (2) | 2.7932 (19) | 174.0 (17) |
N6E—H6EA···O2Dviii | 0.91 (2) | 2.32 (2) | 2.973 (2) | 128.7 (17) |
N6E—H6EA···O3Dviii | 0.91 (2) | 2.06 (2) | 2.8527 (18) | 145.4 (18) |
N6E—H6EB···O3E | 0.87 (2) | 2.19 (2) | 2.9056 (18) | 139.6 (17) |
N6E—H6EB···O4E | 0.87 (2) | 2.33 (2) | 3.010 (2) | 135.3 (16) |
N6E—H6EC···N4Bviii | 0.93 (2) | 1.85 (2) | 2.7750 (19) | 174.0 (19) |
C8A—H8A···O2Bix | 0.95 | 2.46 | 3.0887 (19) | 123 |
C9A—H9A···O5E | 0.95 | 2.43 | 3.243 (2) | 144 |
C12A—H12B···O7Aix | 0.99 | 2.46 | 3.313 (2) | 145 |
C9B—H9B···O5Bi | 0.95 | 2.37 | 3.224 (2) | 150 |
C12B—H12D···O7Cvi | 0.99 | 2.47 | 3.335 (2) | 145 |
C8C—H8C···O5Cvi | 0.95 | 2.33 | 3.194 (2) | 152 |
C9C—H9C···O2Ei | 0.95 | 2.49 | 3.105 (2) | 123 |
C7D—H7D···O5Avi | 0.95 | 2.35 | 3.233 (2) | 155 |
C11D—H11H···O6Avi | 0.99 | 2.55 | 3.421 (2) | 147 |
C12D—H12G···O6Bvii | 0.99 | 2.43 | 3.238 (2) | 139 |
C9E—H9E···O5Dii | 0.95 | 2.27 | 3.162 (6) | 156 |
C9E—H9E···O5DAii | 0.95 | 2.56 | 3.357 (17) | 141 |
C12E—H12I···O6Eviii | 0.99 | 2.34 | 3.186 (2) | 142 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z+1; (viii) x−1/2, −y+1/2, z+1/2; (ix) −x+3/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N6A—H6AA···O3Ei | 0.85 (2) | 2.06 (2) | 2.8943 (18) | 167.5 (18) |
N6A—H6AB···O3Dii | 0.91 (2) | 2.08 (2) | 2.8671 (18) | 143.1 (16) |
N6A—H6AB···O4Dii | 0.91 (2) | 2.25 (2) | 2.961 (2) | 134.6 (15) |
N6A—H6AC···N4C | 0.95 (2) | 1.87 (2) | 2.8157 (19) | 172.5 (18) |
N6B—H6BA···O3Biii | 0.92 (2) | 2.117 (19) | 2.8728 (17) | 138.5 (15) |
N6B—H6BA···O4Biii | 0.92 (2) | 2.268 (19) | 3.006 (2) | 136.6 (15) |
N6B—H6BB···O3B | 0.89 (2) | 2.00 (2) | 2.8502 (17) | 161.0 (19) |
N6B—H6BC···N4Aiv | 0.92 (2) | 1.88 (2) | 2.7988 (19) | 173.4 (17) |
N6C—H6CA···O2Cv | 0.85 (2) | 2.305 (18) | 2.8334 (19) | 120.9 (15) |
N6C—H6CA···O3Cv | 0.85 (2) | 2.10 (2) | 2.8944 (18) | 155.4 (17) |
N6C—H6CB···O3Avi | 0.89 (2) | 2.174 (19) | 2.9145 (18) | 140.2 (16) |
N6C—H6CB···O4Avi | 0.89 (2) | 2.270 (19) | 2.986 (2) | 137.3 (15) |
N6C—H6CC···N4Dvi | 0.92 (2) | 1.91 (2) | 2.8179 (19) | 167.6 (17) |
N6D—H6DA···O2Avii | 0.89 (2) | 2.361 (19) | 2.9631 (19) | 124.9 (15) |
N6D—H6DA···O3Avii | 0.89 (2) | 2.06 (2) | 2.8340 (17) | 145.0 (16) |
N6D—H6DB···O3Cvi | 0.89 (2) | 2.16 (2) | 2.9171 (17) | 142.0 (17) |
N6D—H6DB···O4Cvi | 0.89 (2) | 2.27 (2) | 2.9323 (19) | 130.5 (16) |
N6D—H6DC···N4E | 0.89 (2) | 1.91 (2) | 2.7932 (19) | 174.0 (17) |
N6E—H6EA···O2Dviii | 0.91 (2) | 2.32 (2) | 2.973 (2) | 128.7 (17) |
N6E—H6EA···O3Dviii | 0.91 (2) | 2.06 (2) | 2.8527 (18) | 145.4 (18) |
N6E—H6EB···O3E | 0.87 (2) | 2.19 (2) | 2.9056 (18) | 139.6 (17) |
N6E—H6EB···O4E | 0.87 (2) | 2.33 (2) | 3.010 (2) | 135.3 (16) |
N6E—H6EC···N4Bviii | 0.93 (2) | 1.85 (2) | 2.7750 (19) | 174.0 (19) |
C8A—H8A···O2Bix | 0.95 | 2.46 | 3.0887 (19) | 123.2 |
C9A—H9A···O5E | 0.95 | 2.43 | 3.243 (2) | 143.5 |
C12A—H12B···O7Aix | 0.99 | 2.46 | 3.313 (2) | 144.7 |
C9B—H9B···O5Bi | 0.95 | 2.37 | 3.224 (2) | 149.7 |
C12B—H12D···O7Cvi | 0.99 | 2.47 | 3.335 (2) | 145.2 |
C8C—H8C···O5Cvi | 0.95 | 2.33 | 3.194 (2) | 151.7 |
C9C—H9C···O2Ei | 0.95 | 2.49 | 3.105 (2) | 122.5 |
C7D—H7D···O5Avi | 0.95 | 2.35 | 3.233 (2) | 154.5 |
C11D—H11H···O6Avi | 0.99 | 2.55 | 3.421 (2) | 147.1 |
C12D—H12G···O6Bvii | 0.99 | 2.43 | 3.238 (2) | 138.7 |
C9E—H9E···O5Dii | 0.95 | 2.27 | 3.162 (6) | 155.5 |
C9E—H9E···O5DAii | 0.95 | 2.56 | 3.357 (17) | 141.3 |
C12E—H12I···O6Eviii | 0.99 | 2.34 | 3.186 (2) | 142.3 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z+1; (viii) x−1/2, −y+1/2, z+1/2; (ix) −x+3/2, y−1/2, −z+1/2. |
Acknowledgements
TSY thanks the UOM for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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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.
Compounds with an imidazole ring system have many pharmacological properties and play important roles in biochemical processes (Lombardino & Wiseman, 1974). Many imidazole derivatives are characterized as inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989a,b). Imidazole derivatives are also used as potential anticancer agents (Krezel, 1998) and display a broad spectrum of pharmacological activities. It is well known that picric acid forms charge transfer molecular complexes with a number of aromatic compounds such as aromatic amines through electrostatic or hydrogen bonding interactions (In et al., 1997). Picric acid is a polynitrogen compound with explosive character and imidazolium-based cation picrate salts are good candidates for energetic ionic salts (Jin et al., 2005).
The crystal structures of some imidazolium picrates have been reported, for instance imidazolium picrate itself (Soriano-García et al., 1990), also two solvates (hydrate and ethanolate) of 2-aminohistamine dipicrate (Nardelli et al., 1987), 4-hydroxy methylimidazolium picrate (Du & Zhao, 2003), two polymorphs of betaine bis(diimidazolium) dipicrate (MacDonald et al., 2005) and 3-benzyl-1-methyl-imidazolium picrate (Pi et al., 2009). Recently, we have reported the crystal structure of 2-methylimidazolium picrate (Dutkiewicz et al., 2011).
In view of the importance of imidazoles, this paper reports the crystal structure of the title salt, C6H12N3+ . C6H2N3O7-, (I).
In (I), there are five cation-anion independent pairs (A, B, C, D, E) in the asymmetric unit. For clarity only the C cation-anion pair is displayed in Fig. 1. In the cation the ammonium group is protonated with the aminopropyl group nearly at right angles to the imidazole ring showing C/N/C/C torsion angles ranging from 79.6 (2)° to 99.79 (19)° in the five cations. Bond lengths are in normal ranges (Allen et al., 1987). The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to phenolate oxygen of 26.0 (2)°, 37,3(7)° (A); 28,9(5)°, 35.3 (1)° (B); 34.7 (7)°, 36.9 (7)° (C); 14.7 (4)°, 36.9 (2)° (D); 33.1 (1)°, 35.4 (3)° (E). In contrast the nitro groups in the para positions lie much closer to the aromatic ring plane with angles 1.8 (3)° (A); 3.5 (3)° (B); 6.03° (C); 2.1 (3)° (D); 7.7 (1)° (E), respectively. Disorder is observed in atom O5D, an ortho nitro group in anion D, with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H···O cation-anion and N—H···N cation-cation hydrogen bonds (Table 1) are observed linking the ions into chains along [0 1 0] (Fig. 2). In addition, weak C—H···O cation-anion intermolecular interactions also contribute to packing stability.