research communications
Syntheses and crystal structures of four 4-(4-methoxyphenyl)piperazin-1-ium salts: trifluoroacetate, 2,3,4,5,6-pentafluorobenzoate, 4-iodobenzoate, and a polymorph with 4-methylbenzoate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, and bDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com
Syntheses and X-ray crystal structures of four 4-(4-methoxyphenyl)piperazin-1-ium (MeOPP) salts, with 2,2,2-trifluoroacetate, C11H17N2O+·C2F3O2− (I), 2,3,4,5,6-pentafluorobenzoate, C11H17N2O+·C7F5O2−·H2O (II), 4-iodobenzoate C11H17N2O+·C7H4IO2−·H2O (III), and 4-methylbenzoate, C11H17N2O+·C8H7O2−·H2O (IV) anions are presented. The salts form directly from equimolar quantities of N-(4-methoxyphenyl)piperazine and the corresponding organic acid in methanol and crystallize from 1:1 methanol/ethyl acetate. Salt I is anhydrous whereas II, III, and IV are all monohydrates. In all cases, the MeOPP cation conformation is determined by the torsion about the N—C bond between the piperazinium and 4-methoxybenzene rings. Crystal packing in each structure is largely dictated by N—H⋯O and (in II, III, and IV) O—H⋯O hydrogen bonds, although each also features weak C—H⋯O-type hydrogen bonds. Salt II also has π–π-stacking interactions between cation and anion arene rings, and III exhibits I⋯I close contacts.
1. Chemical context
In recent years, N-(4-methoxyphenyl)piperazine (MeOPP) has emerged as an addition to the range of designer recreational drugs. As such, considerable effort has been invested in the development of methods for the detection both of MeOPP itself and of its metabolites; N-(4-hydroxyphenyl)piperazine and 4-hydroxyaniline (Arbo et al., 2012) in human fluids (Staack & Maurer, 2003; Staack et al., 2004). MeOPP imparts euphoric stimulant properties, its actions on human physiology being similar to those of amphetamines (Staack & Maurer, 2005; Wohlfarth et al., 2010), but it has a significantly lower potential for abuse (Nagai et al., 2007). However, no therapeutic applications of MeOPP have been reported to date. In view of the reported psychoactive properties of MeOPP, coupled with the broad range of biological activities exhibited by piperazine derivatives in general (Asif, 2015; Brito et al., 2019), we recently initiated a programme of study centred on N-(4-methoxyphenyl)piperazine derivatives. Thus far, we have reported the synthesis and structures of a series of 1-aroyl-4-(4-methoxyphenyl) piperazines (Kiran Kumar et al., 2019a). We have also reported a series of 4-methoxyphenyl piperazin-1-ium salts formed with simple organic acids (Kiran Kumar et al., 2019b), and also reported crystal structures of the free-base compound N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts (Kiran Kumar et al., 2020a). More recently, we reported the crystal structures of 4-(4-methoxyphenyl)piperazin-1-ium 4-methylbenzoate monohydrate and bis-[4-(4-methoxyphenyl)piperazin-1-ium] benzene-1,2-dicarboxylate (Shankara Prasad et al., 2022).
In view of the pharmacological importance of piperazines and the use of N-(4-methoxyphenyl)piperazine in particular, this paper presents the syntheses and crystal structures of N-(4-methoxyphenyl)piperazin-1-ium trifluoroacetate, C11H17N2O+·C2F3O2− (I), N-(4-methoxyphenyl)piperazin-1-ium 2,3,4,5,6-pentafluorobenzoate monohydrate, C11H17N2O+·C7F5O2−·H2O (II), N-(4-methoxyphenyl)piperazin-1-ium 4-iodobenzoate monohydrate, C11H17N2O+·C7H4IO2−·H2O (III) and a polymorph of N-(4-methoxyphenyl)piperazin-1-ium 4-methylbenzoate monohydrate, C11H17N2O+·C8H7O2−·H2O (IV).
2. Structural commentary
Three of the four salts (see Figs. 1–4) crystallized as monohydrates; only I is anhydrous. Structure III, which is a much higher quality, low-temperature re-investigation of CSD entry KUJPUD [Kiran Kumar et al., 2020b; CSD = Cambridge Structural Database (Groom et al., 2016)] contains three copies of the cation, anion, and water within its (i.e. Z′ = 3), all others have Z′ = 1. Structure IV is a polymorph of CSD entry XEMCIF (Shankara Prasad et al., 2022). The asymmetric units were chosen so as to make the N—H⋯O hydrogen-bond geometry between the cation and anion as similar as possible, i.e. with the equatorial H atom of the NH2+ group as donor (see section 3: Supramolecular features). The overall conformations of the cations in I–IV are determined, in large part, by the twist of the N2—C5 bonds that connect the 4-methoxyphenyl and piperazinium groups (Figs. 1–4). These twists, quantified for example by the dihedral angle between the mean planes of the benzene ring (C5–C10) and the four carbon atoms (C1–C4) of the piperazinium rings, are 40.63 (5)° (I), 36.05 (4)° (II), 25.28 (13), 26.59 (12), and 24.82 (11)° (for IIIa,b,c, respectively), and 7.57 (8)° (IV), showing moderate variability across the four structures (Fig. 5). The geometry of the N2 atoms in each cation is non-planar; the sums of bond angles about N2 ranging from 337.46 (16)° in I to 342.4 (3)° for N2C in IIIc. In each structure, the 4-methoxy groups are close to coplanar with their attached benzene rings, the largest deviation out of plane being only 0.188 (4) Å for C11C in IIIc, which corresponds to a C9C—C8C—O1C—C11C torsion angle of 172.3 (2)°.
The conformation of the trifluoroacetate anion in I, is largely unremarkable, having a dihedral angle between the plane of the carboxylate group and the plane formed by atoms C12, C13, and F3 of 89.29 (12)°. In the substituted benzoate anions of II, III, and IV, the dihedral angles between the carboxylate groups and the benzene rings are 43.28 (5)° (II), 3.8 (2)°, 7.46 (19)°, and 23.6 (2)° (IIIa,b,c, respectively) and 8.60 (11)° (IV).
3. Supramolecular features
Strong hydrogen bonds are the dominant intermolecular interactions in each of the four salts. All other hydrogen-bond-type interactions are weak. Salt II has weak π–π interactions and III has I⋯I contacts, as described below.
The hydrogen bonding in I is the simplest of the four salts. There are only two N—H⋯O hydrogen bonds, the shortest being N1—H1NA⋯O2, at dD⋯A = 2.7084 (13) Å. In addition, N1—H1NB⋯O3i (symmetry code as per Table 1) at dD⋯A = 2.8329 (14) Å, connects cations and anions into chains that extend parallel to its crystallographic b axis, with inversion-related chains running anti-parallel (Fig. 6). Other than a few C—H⋯O and C—H⋯F close contacts (also listed in Table 1), there are no other significant inter-species interactions.
In II, the chosen includes N1—H1NA⋯O2 as the shortest hydrogen bond, at 2.7464 (12) Å. The cation also hydrogen bonds to an inversion-related anion via N1—H1NB⋯O3i (symmetry operator as per Table 2), dD⋯A = 2.7692 (12) Å. The water molecule acts as donor in two strong O1W—H1W1⋯O3 (same asymmetric unit) and O1W—H2W1⋯O2ii (21 screw-related, as per Table 2) hydrogen bonds, and as acceptor in two weak C—H⋯Owater interactions, as listed in Table 2. There are a few much weaker C—H⋯F close contacts (Table 2). The hydrogen bonding in II is augmented by π–π stacking of the cation benzene ring with 21 screw (−x + 1, y − , −z + ) and inversion-related (1 − x, 1 − y, 1 − z) anion pentafluorobenzene rings. However, the fluorinated rings are 6.03 (3)° out of co-planarity with the MeOPP arene ring and the stacking is offset, leading to centroid–centroid distances of 3.567 (2) Å. The net result is a complicated double-layered structure that extends parallel to the bc plane, a slice through which is shown in Fig. 7.
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The III contains three crystallographically inequivalent groups of cation, anion, and water molecules (Fig. 3). Within each group, the species are hydrogen bonded in a similar pattern to the of II, and the cation–anion pairs are linked by the water molecules. The asymmetric units are linked by O—H⋯Owater hydrogen bonds to glide-related (x, − y, + z and x, − − y, + z) equivalents parallel to c (Figs. 3 and 8). These connections lead to double layers parallel to the ac plane. Details of the hydrogen-bonding interactions are given in Table 3. The double-layers are themselves connected by I⋯I close contacts to an inversion-related [dI⋯I = 3.8586 (4) Å for I1B⋯I1Binv and 4.0444 (4) Å for I1A⋯I1Cinv and I1C⋯I1Ainv (inv = −x, −y, 1 − z)], also depicted in Fig. 8.
of
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In the structure of IV, a strong N1—H1NA⋯O2 [dD⋯A = 2.7391 (15) Å] hydrogen bond links the cation and anion. In combination with hydrogen bonds N1—H1NB⋯O1Wi, O1W—H1W⋯O3, and O1W—H2W⋯O2iv (symmetry codes as per Table 4) involving water molecules, bi-layered tapes in the ac plane extend along the a-axis direction (Fig. 9). There are no other noteworthy interactions other than a few C—H⋯O contacts, which are also listed in Table 4.
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4. Database survey
A search of the Cambridge Structural Database (CSD, v5.43 plus updates to November 2022; Groom et al., 2016) for a search fragment consisting of 1-phenylpiperazine (without substituents) gave 1871 hits. With `any non-H atom' substituted at the 4-position of the benzene ring, but all other carbons bearing hydrogen, a search found 225 matches, 46 of which had the R2H2+ piperazinium cation. This search fragment, but with a methoxy group added at the 4-position of the benzene ring, returned 20 structures. The parent molecule, 4-MeOPP, is present as CSD entry IHILOD (Kiran Kumar et al., 2020a). CSD code EGUROO (Zia-ur-Rehman et al., 2009) is the chloride salt of the 4-MeOPP cation and OMUXIG (Gharbi et al., 2021) is a 4-MeOPP salt with Co(NCS)42– as its anion. The rest are all salts with a variety of organic anions: FOVPEO, FOVPOY, FOVPUE, FOVQAL, FOVQEP, FOVQIT, FOVQOZ, FOVQUF, FOVRAM, FOVREQ, FOVRIU, and FOVROA having been published by Kiran Kumar et al. (2019a). Structures IHILUJ, IHIMAQ, & IHIMEU (along with IHILOD) were also published by Kiran Kumar et al. (2020a), and XEMCIF and XEMCOL by Shankara Prasad et al. (2022). Entry KUJPUD, present as a CSD Communication (Kiran Kumar et al., 2020b), is a poor-quality room-temperature structure of the 4-iodobenzoate, III. Similar related structures include the 1-aroyl-4-(4-methoxyphenyl) piperazines VONFOW, VONGAJ, VONGEN, VONGIR, VONGOX, & VONGUD (Kiran Kumar et al., 2019b).
5. Synthesis and crystallization
All reagents were obtained commercially and were used as received. For the synthesis of the salts, equimolar quantities (0.52 mmol of each component) of N-(4-methoxyphenyl)piperazine (100 mg) (from Sigma-Aldrich) and either trifluoroacetic acid (60 mg, I), pentafluorobenzoic acid (110 mg, II), 4-iodobenzoic acid (129 mg, III), or 4-methylbenzoic acid (71 mg, IV) were separately dissolved in methanol (10 ml). The two solutions were mixed and stirred briefly at 333 K and then set aside to crystallize, giving the solid products I to IV after a few days. The products were collected by filtration and then dried in air (I: yield 80%, m.p. 390–392 K; II: yield 75%, m.p. 375–377 K; III: yield 85%, m.p. 426–428 K; IV: yield 70%, m.p. 406–408 K). Crystals of compounds I to IV suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of solutions in methanol:ethyl acetate (initial composition 1:1, v/v).
6. Refinement
Crystal data, data collection, and . All hydrogen atoms were located in difference-Fourier maps. Those bound to nitrogen or oxygen were refined freely, while carbon-bound hydrogens were included in the using riding models with constrained distances set to 0.95 Å (Csp2H), 0.99 Å (R2CH2), and 0.98 Å (RCH3) using Uiso(H) values constrained to 1.2Ueq or 1.5Ueq (methyl only) of the attached carbon atom.
are given in Table 5
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Supporting information
https://doi.org/10.1107/S2056989023002529/vm2279sup1.cif
contains datablocks I, II, III, IV, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023002529/vm2279Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023002529/vm2279IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023002529/vm2279IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989023002529/vm2279IVsup5.hkl
For all structures, data collection: APEX3 (Bruker, 2016); cell
APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010).C11H17N2O+·C2F3O2− | Dx = 1.443 Mg m−3 |
Mr = 306.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9961 reflections |
a = 16.2967 (9) Å | θ = 2.5–27.5° |
b = 6.0887 (2) Å | µ = 0.13 mm−1 |
c = 28.4139 (15) Å | T = 90 K |
V = 2819.4 (2) Å3 | Solvent-rounded block, colourless |
Z = 8 | 0.24 × 0.18 × 0.11 mm |
F(000) = 1280 |
Bruker D8 Venture dual source diffractometer | 3243 independent reflections |
Radiation source: microsource | 2802 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.038 |
φ and ω scans | θmax = 27.6°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −20→21 |
Tmin = 0.847, Tmax = 0.958 | k = −7→7 |
26032 measured reflections | l = −36→37 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0351P)2 + 1.3982P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3243 reflections | Δρmax = 0.39 e Å−3 |
200 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (7) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
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. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.64348 (5) | 0.88138 (14) | 0.84741 (3) | 0.01761 (19) | |
N1 | 0.57880 (6) | 0.57351 (17) | 0.56220 (3) | 0.0147 (2) | |
H1A | 0.5746 (10) | 0.487 (3) | 0.5350 (6) | 0.029 (4)* | |
H1B | 0.5680 (9) | 0.713 (3) | 0.5535 (5) | 0.023 (4)* | |
N2 | 0.61770 (6) | 0.60018 (16) | 0.66037 (3) | 0.0155 (2) | |
C1 | 0.66484 (7) | 0.5639 (2) | 0.57944 (4) | 0.0179 (2) | |
H1C | 0.702091 | 0.626714 | 0.555436 | 0.022* | |
H1D | 0.680835 | 0.408985 | 0.584747 | 0.022* | |
C2 | 0.67297 (7) | 0.6921 (2) | 0.62512 (4) | 0.0172 (2) | |
H2A | 0.730261 | 0.684243 | 0.636575 | 0.021* | |
H2B | 0.659190 | 0.848350 | 0.619580 | 0.021* | |
C3 | 0.53255 (7) | 0.6192 (2) | 0.64390 (4) | 0.0179 (2) | |
H3A | 0.519051 | 0.775947 | 0.638751 | 0.022* | |
H3B | 0.494967 | 0.561212 | 0.668281 | 0.022* | |
C4 | 0.52025 (7) | 0.4935 (2) | 0.59861 (4) | 0.0181 (2) | |
H4A | 0.529255 | 0.334880 | 0.604256 | 0.022* | |
H4B | 0.463242 | 0.513595 | 0.587369 | 0.022* | |
C5 | 0.62749 (7) | 0.68174 (19) | 0.70730 (4) | 0.0155 (2) | |
C6 | 0.67365 (7) | 0.8657 (2) | 0.71851 (4) | 0.0186 (3) | |
H6 | 0.700715 | 0.944071 | 0.694126 | 0.022* | |
C7 | 0.68114 (7) | 0.9382 (2) | 0.76507 (4) | 0.0186 (2) | |
H7 | 0.713564 | 1.063514 | 0.772171 | 0.022* | |
C8 | 0.64107 (7) | 0.82630 (19) | 0.80068 (4) | 0.0154 (2) | |
C9 | 0.59454 (7) | 0.6405 (2) | 0.78982 (4) | 0.0176 (2) | |
H9 | 0.567039 | 0.563175 | 0.814201 | 0.021* | |
C10 | 0.58821 (7) | 0.5683 (2) | 0.74383 (4) | 0.0182 (2) | |
H10 | 0.556949 | 0.440604 | 0.736930 | 0.022* | |
C11 | 0.68848 (8) | 1.0742 (2) | 0.85963 (4) | 0.0216 (3) | |
H11A | 0.683518 | 1.100895 | 0.893519 | 0.032* | |
H11B | 0.666423 | 1.200190 | 0.842301 | 0.032* | |
H11C | 0.746404 | 1.053795 | 0.851455 | 0.032* | |
F1 | 0.62003 (5) | −0.25022 (11) | 0.46795 (3) | 0.02609 (19) | |
F2 | 0.60056 (6) | 0.00973 (14) | 0.41859 (3) | 0.0388 (2) | |
F3 | 0.71197 (5) | −0.00256 (16) | 0.45876 (4) | 0.0485 (3) | |
O2 | 0.57475 (6) | 0.29613 (14) | 0.48772 (3) | 0.0226 (2) | |
O3 | 0.59231 (7) | 0.02571 (15) | 0.54005 (3) | 0.0290 (2) | |
C12 | 0.59453 (7) | 0.10857 (19) | 0.50037 (4) | 0.0151 (2) | |
C13 | 0.63112 (8) | −0.0358 (2) | 0.46090 (4) | 0.0198 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0188 (4) | 0.0216 (4) | 0.0124 (4) | −0.0011 (3) | −0.0001 (3) | −0.0024 (3) |
N1 | 0.0180 (5) | 0.0138 (5) | 0.0124 (4) | 0.0007 (4) | −0.0012 (4) | 0.0000 (4) |
N2 | 0.0148 (5) | 0.0202 (5) | 0.0114 (4) | −0.0027 (4) | −0.0008 (3) | 0.0002 (4) |
C1 | 0.0156 (5) | 0.0232 (6) | 0.0150 (5) | 0.0022 (5) | −0.0001 (4) | 0.0000 (4) |
C2 | 0.0146 (5) | 0.0231 (6) | 0.0138 (5) | −0.0026 (4) | 0.0002 (4) | 0.0011 (4) |
C3 | 0.0145 (5) | 0.0252 (6) | 0.0141 (5) | −0.0023 (4) | −0.0008 (4) | −0.0013 (4) |
C4 | 0.0178 (5) | 0.0228 (6) | 0.0137 (5) | −0.0044 (5) | −0.0009 (4) | −0.0002 (4) |
C5 | 0.0151 (5) | 0.0184 (5) | 0.0128 (5) | 0.0001 (4) | −0.0015 (4) | 0.0003 (4) |
C6 | 0.0195 (6) | 0.0218 (6) | 0.0147 (5) | −0.0048 (5) | 0.0004 (4) | 0.0024 (4) |
C7 | 0.0199 (6) | 0.0188 (6) | 0.0169 (5) | −0.0050 (5) | −0.0019 (4) | −0.0008 (4) |
C8 | 0.0145 (5) | 0.0186 (6) | 0.0130 (5) | 0.0028 (4) | −0.0016 (4) | −0.0009 (4) |
C9 | 0.0169 (5) | 0.0209 (6) | 0.0150 (5) | −0.0020 (5) | 0.0007 (4) | 0.0027 (4) |
C10 | 0.0191 (6) | 0.0185 (6) | 0.0170 (5) | −0.0044 (5) | −0.0012 (4) | 0.0002 (4) |
C11 | 0.0234 (6) | 0.0235 (6) | 0.0181 (5) | −0.0025 (5) | −0.0022 (5) | −0.0047 (5) |
F1 | 0.0437 (5) | 0.0128 (4) | 0.0218 (4) | 0.0006 (3) | 0.0057 (3) | −0.0020 (3) |
F2 | 0.0776 (7) | 0.0254 (4) | 0.0134 (4) | 0.0096 (4) | 0.0024 (4) | −0.0011 (3) |
F3 | 0.0268 (5) | 0.0461 (6) | 0.0725 (7) | −0.0087 (4) | 0.0245 (4) | −0.0251 (5) |
O2 | 0.0341 (5) | 0.0161 (4) | 0.0174 (4) | 0.0053 (4) | −0.0032 (4) | −0.0013 (3) |
O3 | 0.0552 (7) | 0.0175 (4) | 0.0144 (4) | 0.0027 (4) | 0.0036 (4) | 0.0009 (3) |
C12 | 0.0155 (5) | 0.0144 (5) | 0.0154 (5) | −0.0020 (4) | −0.0001 (4) | −0.0018 (4) |
C13 | 0.0247 (6) | 0.0155 (6) | 0.0192 (6) | −0.0020 (5) | 0.0054 (5) | 0.0002 (4) |
O1—C8 | 1.3701 (13) | C5—C6 | 1.3862 (16) |
O1—C11 | 1.4269 (15) | C5—C10 | 1.4015 (16) |
N1—C1 | 1.4864 (15) | C6—C7 | 1.3998 (16) |
N1—C4 | 1.4893 (14) | C6—H6 | 0.9500 |
N1—H1A | 0.937 (16) | C7—C8 | 1.3835 (16) |
N1—H1B | 0.901 (16) | C7—H7 | 0.9500 |
N2—C5 | 1.4318 (14) | C8—C9 | 1.3964 (17) |
N2—C2 | 1.4587 (14) | C9—C10 | 1.3824 (16) |
N2—C3 | 1.4692 (14) | C9—H9 | 0.9500 |
C1—C2 | 1.5205 (16) | C10—H10 | 0.9500 |
C1—H1C | 0.9900 | C11—H11A | 0.9800 |
C1—H1D | 0.9900 | C11—H11B | 0.9800 |
C2—H2A | 0.9900 | C11—H11C | 0.9800 |
C2—H2B | 0.9900 | F1—C13 | 1.3333 (14) |
C3—C4 | 1.5106 (15) | F2—C13 | 1.3306 (14) |
C3—H3A | 0.9900 | F3—C13 | 1.3343 (15) |
C3—H3B | 0.9900 | O2—C12 | 1.2399 (14) |
C4—H4A | 0.9900 | O3—C12 | 1.2356 (14) |
C4—H4B | 0.9900 | C12—C13 | 1.5445 (16) |
C8—O1—C11 | 116.87 (9) | C6—C5—C10 | 118.42 (10) |
C1—N1—C4 | 111.25 (9) | C6—C5—N2 | 123.69 (10) |
C1—N1—H1A | 108.6 (10) | C10—C5—N2 | 117.9 (1) |
C4—N1—H1A | 110 (1) | C5—C6—C7 | 121.28 (11) |
C1—N1—H1B | 108.1 (9) | C5—C6—H6 | 119.4 |
C4—N1—H1B | 111.9 (9) | C7—C6—H6 | 119.4 |
H1A—N1—H1B | 106.9 (13) | C8—C7—C6 | 119.65 (11) |
C5—N2—C2 | 115.95 (9) | C8—C7—H7 | 120.2 |
C5—N2—C3 | 112.00 (9) | C6—C7—H7 | 120.2 |
C2—N2—C3 | 109.51 (9) | O1—C8—C7 | 125.08 (11) |
N1—C1—C2 | 110.07 (9) | O1—C8—C9 | 115.34 (10) |
N1—C1—H1C | 109.6 | C7—C8—C9 | 119.57 (10) |
C2—C1—H1C | 109.6 | C10—C9—C8 | 120.46 (11) |
N1—C1—H1D | 109.6 | C10—C9—H9 | 119.8 |
C2—C1—H1D | 109.6 | C8—C9—H9 | 119.8 |
H1C—C1—H1D | 108.2 | C9—C10—C5 | 120.61 (11) |
N2—C2—C1 | 109.59 (9) | C9—C10—H10 | 119.7 |
N2—C2—H2A | 109.8 | C5—C10—H10 | 119.7 |
C1—C2—H2A | 109.8 | O1—C11—H11A | 109.5 |
N2—C2—H2B | 109.8 | O1—C11—H11B | 109.5 |
C1—C2—H2B | 109.8 | H11A—C11—H11B | 109.5 |
H2A—C2—H2B | 108.2 | O1—C11—H11C | 109.5 |
N2—C3—C4 | 110.90 (9) | H11A—C11—H11C | 109.5 |
N2—C3—H3A | 109.5 | H11B—C11—H11C | 109.5 |
C4—C3—H3A | 109.5 | O3—C12—O2 | 129.27 (11) |
N2—C3—H3B | 109.5 | O3—C12—C13 | 116.19 (10) |
C4—C3—H3B | 109.5 | O2—C12—C13 | 114.45 (10) |
H3A—C3—H3B | 108.0 | F2—C13—F1 | 106.79 (10) |
N1—C4—C3 | 109.93 (9) | F2—C13—F3 | 107.26 (11) |
N1—C4—H4A | 109.7 | F1—C13—F3 | 106.81 (11) |
C3—C4—H4A | 109.7 | F2—C13—C12 | 113.14 (10) |
N1—C4—H4B | 109.7 | F1—C13—C12 | 113.32 (9) |
C3—C4—H4B | 109.7 | F3—C13—C12 | 109.16 (10) |
H4A—C4—H4B | 108.2 | ||
C4—N1—C1—C2 | −55.67 (12) | C11—O1—C8—C7 | 2.48 (16) |
C5—N2—C2—C1 | 170.74 (9) | C11—O1—C8—C9 | −178.21 (10) |
C3—N2—C2—C1 | −61.35 (12) | C6—C7—C8—O1 | −179.82 (11) |
N1—C1—C2—N2 | 58.98 (12) | C6—C7—C8—C9 | 0.89 (18) |
C5—N2—C3—C4 | −168.97 (9) | O1—C8—C9—C10 | −179.47 (10) |
C2—N2—C3—C4 | 60.94 (12) | C7—C8—C9—C10 | −0.12 (18) |
C1—N1—C4—C3 | 54.44 (12) | C8—C9—C10—C5 | −0.80 (18) |
N2—C3—C4—N1 | −56.90 (12) | C6—C5—C10—C9 | 0.91 (18) |
C2—N2—C5—C6 | 12.65 (16) | N2—C5—C10—C9 | −179.22 (11) |
C3—N2—C5—C6 | −114.02 (12) | O3—C12—C13—F2 | 151.49 (11) |
C2—N2—C5—C10 | −167.21 (10) | O2—C12—C13—F2 | −31.49 (15) |
C3—N2—C5—C10 | 66.12 (13) | O3—C12—C13—F1 | 29.73 (16) |
C10—C5—C6—C7 | −0.13 (18) | O2—C12—C13—F1 | −153.24 (11) |
N2—C5—C6—C7 | −179.99 (11) | O3—C12—C13—F3 | −89.16 (13) |
C5—C6—C7—C8 | −0.78 (18) | O2—C12—C13—F3 | 87.86 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.937 (16) | 1.777 (16) | 2.7084 (13) | 172.1 (15) |
N1—H1B···O3i | 0.901 (16) | 1.982 (16) | 2.8329 (14) | 156.7 (13) |
C3—H3B···O1ii | 0.99 | 2.55 | 3.2230 (14) | 125 |
C4—H4B···F1iii | 0.99 | 2.62 | 3.3162 (14) | 127 |
C4—H4B···O2iv | 0.99 | 2.51 | 3.1709 (14) | 124 |
C11—H11A···F3v | 0.98 | 2.59 | 3.2796 (15) | 128 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, −y+1, z+1/2. |
C11H17N2O+·C7F5O2−·H2O | F(000) = 872 |
Mr = 422.35 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.9733 (7) Å | Cell parameters from 9821 reflections |
b = 8.3512 (4) Å | θ = 2.9–27.5° |
c = 13.2980 (4) Å | µ = 0.14 mm−1 |
β = 101.494 (1)° | T = 90 K |
V = 1847.16 (13) Å3 | Colourless block, colourless |
Z = 4 | 0.30 × 0.29 × 0.14 mm |
Bruker D8 Venture dual source diffractometer | 4238 independent reflections |
Radiation source: microsource | 3793 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.031 |
φ and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −22→22 |
Tmin = 0.919, Tmax = 0.971 | k = −10→10 |
30724 measured reflections | l = −16→17 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0401P)2 + 0.7353P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4238 reflections | Δρmax = 0.34 e Å−3 |
280 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0073 (14) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
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. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.58113 (6) | 0.83766 (11) | 0.41244 (7) | 0.01666 (19) | |
H1A | 0.5398 (10) | 0.8859 (19) | 0.3686 (12) | 0.031 (4)* | |
H1B | 0.5880 (8) | 0.8844 (17) | 0.4730 (11) | 0.022 (3)* | |
N2 | 0.70053 (5) | 0.59211 (11) | 0.44294 (7) | 0.01513 (19) | |
C1 | 0.65689 (6) | 0.85334 (13) | 0.37269 (8) | 0.0179 (2) | |
H1C | 0.672233 | 0.967644 | 0.371987 | 0.021* | |
H1D | 0.648215 | 0.812662 | 0.301405 | 0.021* | |
C2 | 0.72406 (6) | 0.75953 (13) | 0.43956 (8) | 0.0167 (2) | |
H2A | 0.773654 | 0.767857 | 0.411334 | 0.020* | |
H2B | 0.735304 | 0.804590 | 0.509829 | 0.020* | |
C3 | 0.62849 (6) | 0.57710 (13) | 0.48786 (8) | 0.0169 (2) | |
H3A | 0.639553 | 0.621541 | 0.558294 | 0.020* | |
H3B | 0.614304 | 0.462636 | 0.492007 | 0.020* | |
C4 | 0.55894 (6) | 0.66628 (13) | 0.42271 (8) | 0.0180 (2) | |
H4A | 0.545082 | 0.616403 | 0.353911 | 0.022* | |
H4B | 0.511236 | 0.659600 | 0.454907 | 0.022* | |
C5 | 0.76277 (6) | 0.48023 (13) | 0.48036 (8) | 0.0148 (2) | |
C6 | 0.84193 (6) | 0.52426 (13) | 0.51938 (8) | 0.0177 (2) | |
H6 | 0.855236 | 0.634658 | 0.527225 | 0.021* | |
C7 | 0.90243 (6) | 0.40977 (14) | 0.54733 (8) | 0.0188 (2) | |
H7 | 0.956319 | 0.442453 | 0.572825 | 0.023* | |
C8 | 0.88343 (6) | 0.24844 (13) | 0.53767 (8) | 0.0172 (2) | |
C9 | 0.80383 (6) | 0.20298 (13) | 0.50119 (8) | 0.0167 (2) | |
H9 | 0.790398 | 0.092463 | 0.495695 | 0.020* | |
C10 | 0.74434 (6) | 0.31594 (13) | 0.47297 (8) | 0.0161 (2) | |
H10 | 0.690445 | 0.282547 | 0.448333 | 0.019* | |
O1 | 0.93660 (5) | 0.1247 (1) | 0.56258 (7) | 0.02279 (19) | |
C11 | 1.01917 (7) | 0.16511 (16) | 0.59700 (11) | 0.0303 (3) | |
H11A | 1.051593 | 0.067127 | 0.605706 | 0.045* | |
H11B | 1.025929 | 0.221583 | 0.662767 | 0.045* | |
H11C | 1.036751 | 0.234384 | 0.546209 | 0.045* | |
F1 | 0.24103 (4) | 1.14509 (8) | 0.27860 (5) | 0.02317 (16) | |
O2 | 0.43941 (5) | 0.89873 (9) | 0.27760 (6) | 0.01884 (17) | |
O3 | 0.39764 (5) | 1.07117 (10) | 0.38371 (6) | 0.02156 (18) | |
C12 | 0.38699 (6) | 0.95869 (13) | 0.32036 (8) | 0.0156 (2) | |
C13 | 0.30287 (6) | 0.88933 (13) | 0.29215 (8) | 0.0154 (2) | |
C14 | 0.23480 (7) | 0.98503 (13) | 0.27223 (8) | 0.0177 (2) | |
C15 | 0.15862 (7) | 0.92190 (15) | 0.24210 (8) | 0.0209 (2) | |
C16 | 0.14848 (7) | 0.75875 (15) | 0.23275 (8) | 0.0216 (2) | |
C17 | 0.21451 (7) | 0.65934 (14) | 0.25387 (8) | 0.0197 (2) | |
C18 | 0.29016 (6) | 0.72513 (13) | 0.28256 (8) | 0.0167 (2) | |
F2 | 0.09439 (4) | 1.01803 (10) | 0.22123 (6) | 0.02973 (18) | |
F3 | 0.07470 (4) | 0.69754 (10) | 0.20350 (6) | 0.03065 (18) | |
F4 | 0.20518 (4) | 0.50048 (8) | 0.24420 (6) | 0.02718 (17) | |
F5 | 0.35283 (4) | 0.62368 (8) | 0.30265 (5) | 0.02060 (15) | |
O1W | 0.55228 (5) | 1.20201 (11) | 0.39344 (7) | 0.02363 (19) | |
H1W | 0.5037 (11) | 1.169 (2) | 0.3840 (13) | 0.044 (5)* | |
H2W | 0.5556 (10) | 1.258 (2) | 0.3366 (14) | 0.041 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0179 (4) | 0.0149 (5) | 0.0171 (4) | 0.0024 (3) | 0.0031 (3) | −0.0009 (4) |
N2 | 0.0149 (4) | 0.0126 (4) | 0.0183 (4) | 0.0000 (3) | 0.0044 (3) | 0.0013 (3) |
C1 | 0.0185 (5) | 0.0161 (5) | 0.0196 (5) | 0.0011 (4) | 0.0054 (4) | 0.0026 (4) |
C2 | 0.0167 (5) | 0.0139 (5) | 0.0196 (5) | −0.0015 (4) | 0.0037 (4) | 0.0011 (4) |
C3 | 0.0175 (5) | 0.0156 (5) | 0.0191 (5) | 0.0003 (4) | 0.0068 (4) | 0.0010 (4) |
C4 | 0.0171 (5) | 0.0154 (5) | 0.0220 (5) | −0.0008 (4) | 0.0053 (4) | −0.0015 (4) |
C5 | 0.0170 (5) | 0.0152 (5) | 0.0129 (4) | 0.0009 (4) | 0.0044 (4) | 0.0010 (4) |
C6 | 0.0181 (5) | 0.0142 (5) | 0.0208 (5) | −0.0013 (4) | 0.0042 (4) | 0.0009 (4) |
C7 | 0.0155 (5) | 0.0187 (5) | 0.0219 (5) | −0.0014 (4) | 0.0026 (4) | 0.0009 (4) |
C8 | 0.0192 (5) | 0.0167 (5) | 0.0162 (5) | 0.0035 (4) | 0.0048 (4) | 0.0018 (4) |
C9 | 0.0219 (5) | 0.0133 (5) | 0.0148 (5) | −0.0012 (4) | 0.0038 (4) | −0.0007 (4) |
C10 | 0.0175 (5) | 0.0165 (5) | 0.0142 (5) | −0.0013 (4) | 0.0032 (4) | −0.0009 (4) |
O1 | 0.0184 (4) | 0.0174 (4) | 0.0313 (4) | 0.0037 (3) | 0.0018 (3) | 0.0020 (3) |
C11 | 0.0179 (6) | 0.0245 (6) | 0.0469 (8) | 0.0051 (5) | 0.0026 (5) | 0.0027 (6) |
F1 | 0.0273 (4) | 0.0147 (3) | 0.0285 (4) | 0.0039 (3) | 0.0082 (3) | 0.0034 (3) |
O2 | 0.0170 (4) | 0.0195 (4) | 0.0199 (4) | 0.0015 (3) | 0.0034 (3) | −0.0017 (3) |
O3 | 0.0245 (4) | 0.0205 (4) | 0.0205 (4) | −0.0054 (3) | 0.0062 (3) | −0.0059 (3) |
C12 | 0.0187 (5) | 0.0140 (5) | 0.0139 (5) | −0.0003 (4) | 0.0025 (4) | 0.0026 (4) |
C13 | 0.0187 (5) | 0.0161 (5) | 0.0117 (4) | −0.0004 (4) | 0.0037 (4) | 0.0007 (4) |
C14 | 0.0228 (5) | 0.0154 (5) | 0.0156 (5) | 0.0004 (4) | 0.0057 (4) | 0.0020 (4) |
C15 | 0.0180 (5) | 0.0270 (6) | 0.0179 (5) | 0.0041 (4) | 0.0040 (4) | 0.0034 (4) |
C16 | 0.0183 (5) | 0.0306 (6) | 0.0160 (5) | −0.0073 (5) | 0.0035 (4) | −0.0019 (4) |
C17 | 0.0264 (6) | 0.0177 (5) | 0.0161 (5) | −0.0063 (4) | 0.0070 (4) | −0.0030 (4) |
C18 | 0.0209 (5) | 0.0173 (5) | 0.0126 (5) | 0.0016 (4) | 0.0048 (4) | 0.0004 (4) |
F2 | 0.0194 (3) | 0.0367 (4) | 0.0325 (4) | 0.0090 (3) | 0.0037 (3) | 0.0066 (3) |
F3 | 0.0199 (3) | 0.0418 (5) | 0.0297 (4) | −0.0113 (3) | 0.0036 (3) | −0.0063 (3) |
F4 | 0.0343 (4) | 0.0184 (4) | 0.0309 (4) | −0.0098 (3) | 0.0116 (3) | −0.0072 (3) |
F5 | 0.0246 (3) | 0.0146 (3) | 0.0230 (3) | 0.0033 (3) | 0.0056 (3) | 0.0009 (2) |
O1W | 0.0209 (4) | 0.0256 (5) | 0.0233 (4) | −0.0050 (3) | 0.0019 (3) | 0.0035 (3) |
N1—C1 | 1.4903 (14) | C8—C9 | 1.3941 (15) |
N1—C4 | 1.4932 (14) | C9—C10 | 1.3782 (15) |
N1—H1A | 0.912 (16) | C9—H9 | 0.9500 |
N1—H1B | 0.882 (15) | C10—H10 | 0.9500 |
N2—C5 | 1.4237 (13) | O1—C11 | 1.4254 (14) |
N2—C2 | 1.4573 (13) | C11—H11A | 0.9800 |
N2—C3 | 1.4693 (13) | C11—H11B | 0.9800 |
C1—C2 | 1.5167 (15) | C11—H11C | 0.9800 |
C1—H1C | 0.9900 | F1—C14 | 1.3422 (13) |
C1—H1D | 0.9900 | O2—C12 | 1.2519 (13) |
C2—H2A | 0.9900 | O3—C12 | 1.2506 (13) |
C2—H2B | 0.9900 | C12—C13 | 1.5169 (15) |
C3—C4 | 1.5137 (15) | C13—C14 | 1.3863 (15) |
C3—H3A | 0.9900 | C13—C18 | 1.3900 (15) |
C3—H3B | 0.9900 | C14—C15 | 1.3798 (16) |
C4—H4A | 0.9900 | C15—F2 | 1.3377 (13) |
C4—H4B | 0.9900 | C15—C16 | 1.3758 (17) |
C5—C6 | 1.3900 (15) | C16—F3 | 1.3366 (13) |
C5—C10 | 1.4064 (15) | C16—C17 | 1.3780 (17) |
C6—C7 | 1.3981 (15) | C17—F4 | 1.3392 (13) |
C6—H6 | 0.9500 | C17—C18 | 1.3788 (15) |
C7—C8 | 1.3853 (16) | C18—F5 | 1.3444 (12) |
C7—H7 | 0.9500 | O1W—H1W | 0.854 (19) |
C8—O1 | 1.3686 (13) | O1W—H2W | 0.899 (18) |
C1—N1—C4 | 111.58 (8) | C8—C7—H7 | 120.2 |
C1—N1—H1A | 110.1 (10) | C6—C7—H7 | 120.2 |
C4—N1—H1A | 107.8 (10) | O1—C8—C7 | 125.57 (10) |
C1—N1—H1B | 108.6 (9) | O1—C8—C9 | 115.16 (10) |
C4—N1—H1B | 109.3 (9) | C7—C8—C9 | 119.25 (10) |
H1A—N1—H1B | 109.5 (13) | C10—C9—C8 | 121.0 (1) |
C5—N2—C2 | 116.85 (8) | C10—C9—H9 | 119.5 |
C5—N2—C3 | 114.93 (8) | C8—C9—H9 | 119.5 |
C2—N2—C3 | 110.47 (8) | C9—C10—C5 | 120.54 (10) |
N1—C1—C2 | 110.35 (9) | C9—C10—H10 | 119.7 |
N1—C1—H1C | 109.6 | C5—C10—H10 | 119.7 |
C2—C1—H1C | 109.6 | C8—O1—C11 | 117.24 (9) |
N1—C1—H1D | 109.6 | O1—C11—H11A | 109.5 |
C2—C1—H1D | 109.6 | O1—C11—H11B | 109.5 |
H1C—C1—H1D | 108.1 | H11A—C11—H11B | 109.5 |
N2—C2—C1 | 109.57 (9) | O1—C11—H11C | 109.5 |
N2—C2—H2A | 109.8 | H11A—C11—H11C | 109.5 |
C1—C2—H2A | 109.8 | H11B—C11—H11C | 109.5 |
N2—C2—H2B | 109.8 | O3—C12—O2 | 125.87 (10) |
C1—C2—H2B | 109.8 | O3—C12—C13 | 117.13 (9) |
H2A—C2—H2B | 108.2 | O2—C12—C13 | 117.00 (9) |
N2—C3—C4 | 110.04 (8) | C14—C13—C18 | 116.3 (1) |
N2—C3—H3A | 109.7 | C14—C13—C12 | 122.31 (10) |
C4—C3—H3A | 109.7 | C18—C13—C12 | 121.37 (10) |
N2—C3—H3B | 109.7 | F1—C14—C15 | 117.15 (10) |
C4—C3—H3B | 109.7 | F1—C14—C13 | 120.66 (10) |
H3A—C3—H3B | 108.2 | C15—C14—C13 | 122.16 (10) |
N1—C4—C3 | 109.99 (9) | F2—C15—C16 | 119.56 (10) |
N1—C4—H4A | 109.7 | F2—C15—C14 | 120.58 (11) |
C3—C4—H4A | 109.7 | C16—C15—C14 | 119.86 (11) |
N1—C4—H4B | 109.7 | F3—C16—C15 | 119.88 (11) |
C3—C4—H4B | 109.7 | F3—C16—C17 | 120.37 (11) |
H4A—C4—H4B | 108.2 | C15—C16—C17 | 119.74 (10) |
C6—C5—C10 | 117.98 (10) | F4—C17—C16 | 120.1 (1) |
C6—C5—N2 | 123.48 (10) | F4—C17—C18 | 120.47 (10) |
C10—C5—N2 | 118.47 (9) | C16—C17—C18 | 119.41 (11) |
C5—C6—C7 | 121.5 (1) | F5—C18—C17 | 117.4 (1) |
C5—C6—H6 | 119.2 | F5—C18—C13 | 120.09 (10) |
C7—C6—H6 | 119.2 | C17—C18—C13 | 122.51 (10) |
C8—C7—C6 | 119.69 (10) | H1W—O1W—H2W | 105.2 (15) |
C4—N1—C1—C2 | −54.78 (11) | O3—C12—C13—C18 | −137.95 (11) |
C5—N2—C2—C1 | 164.82 (8) | O2—C12—C13—C18 | 42.46 (14) |
C3—N2—C2—C1 | −61.29 (11) | C18—C13—C14—F1 | −179.42 (9) |
N1—C1—C2—N2 | 57.64 (11) | C12—C13—C14—F1 | −0.87 (15) |
C5—N2—C3—C4 | −163.83 (9) | C18—C13—C14—C15 | −1.53 (15) |
C2—N2—C3—C4 | 61.33 (11) | C12—C13—C14—C15 | 177.02 (10) |
C1—N1—C4—C3 | 54.36 (11) | F1—C14—C15—F2 | −0.50 (15) |
N2—C3—C4—N1 | −56.94 (11) | C13—C14—C15—F2 | −178.46 (9) |
C2—N2—C5—C6 | 4.50 (14) | F1—C14—C15—C16 | 179.1 (1) |
C3—N2—C5—C6 | −127.38 (11) | C13—C14—C15—C16 | 1.14 (16) |
C2—N2—C5—C10 | −172.24 (9) | F2—C15—C16—F3 | −0.35 (16) |
C3—N2—C5—C10 | 55.87 (12) | C14—C15—C16—F3 | −179.95 (9) |
C10—C5—C6—C7 | 2.19 (15) | F2—C15—C16—C17 | 179.80 (9) |
N2—C5—C6—C7 | −174.57 (10) | C14—C15—C16—C17 | 0.20 (17) |
C5—C6—C7—C8 | −1.00 (16) | F3—C16—C17—F4 | 0.66 (16) |
C6—C7—C8—O1 | −179.7 (1) | C15—C16—C17—F4 | −179.49 (10) |
C6—C7—C8—C9 | −0.72 (16) | F3—C16—C17—C18 | 179.11 (9) |
O1—C8—C9—C10 | −179.72 (9) | C15—C16—C17—C18 | −1.04 (16) |
C7—C8—C9—C10 | 1.19 (16) | F4—C17—C18—F5 | −1.69 (15) |
C8—C9—C10—C5 | 0.04 (16) | C16—C17—C18—F5 | 179.86 (9) |
C6—C5—C10—C9 | −1.71 (15) | F4—C17—C18—C13 | 179.05 (10) |
N2—C5—C10—C9 | 175.22 (9) | C16—C17—C18—C13 | 0.60 (16) |
C7—C8—O1—C11 | −3.02 (16) | C14—C13—C18—F5 | −178.58 (9) |
C9—C8—O1—C11 | 177.96 (10) | C12—C13—C18—F5 | 2.86 (15) |
O3—C12—C13—C14 | 43.57 (14) | C14—C13—C18—C17 | 0.66 (15) |
O2—C12—C13—C14 | −136.02 (11) | C12—C13—C18—C17 | −177.91 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.912 (16) | 1.886 (16) | 2.7464 (12) | 156.5 (14) |
N1—H1B···O3i | 0.882 (15) | 1.909 (15) | 2.7692 (12) | 164.9 (13) |
C1—H1C···F5ii | 0.99 | 2.62 | 3.2261 (12) | 119 |
C3—H3B···O1Wiii | 0.99 | 2.65 | 3.5235 (14) | 148 |
C4—H4A···O2iv | 0.99 | 2.57 | 3.4812 (13) | 153 |
C10—H10···O1Wiii | 0.95 | 2.41 | 3.3581 (14) | 177 |
C11—H11A···F3v | 0.98 | 2.55 | 3.3961 (15) | 144 |
C11—H11B···F2vi | 0.98 | 2.51 | 3.2436 (15) | 131 |
O1W—H1W···O3 | 0.854 (19) | 1.978 (19) | 2.8222 (12) | 170.0 (17) |
O1W—H2W···O2ii | 0.899 (18) | 1.936 (19) | 2.8319 (12) | 173.7 (16) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, −y+1/2, z+1/2; (vi) x+1, −y+3/2, z+1/2. |
C11H17N2O+·C7H4IO2−·H2O | F(000) = 2760 |
Mr = 458.28 | Dx = 1.640 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.4117 (18) Å | Cell parameters from 9052 reflections |
b = 7.4255 (6) Å | θ = 2.3–27.5° |
c = 36.796 (3) Å | µ = 1.75 mm−1 |
β = 92.970 (3)° | T = 90 K |
V = 5569.6 (8) Å3 | Plate, colourless |
Z = 12 | 0.30 × 0.13 × 0.03 mm |
Bruker D8 Venture dual source diffractometer | 12876 independent reflections |
Radiation source: microsource | 10003 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.056 |
φ and ω scans | θmax = 27.7°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −26→26 |
Tmin = 0.726, Tmax = 0.862 | k = −9→6 |
72181 measured reflections | l = −47→47 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0216P)2 + 1.7628P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
12876 reflections | Δρmax = 0.84 e Å−3 |
729 parameters | Δρmin = −0.80 e Å−3 |
12 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00017 (3) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
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. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | ||
O1W | 0.43969 (10) | 0.2205 (3) | 0.70712 (5) | 0.0221 (4) | |
H1W1 | 0.4236 (15) | 0.181 (4) | 0.7238 (6) | 0.043 (10)* | |
H2W1 | 0.4260 (15) | 0.166 (4) | 0.6906 (6) | 0.043 (10)* | |
O2W | 0.46521 (10) | 0.3419 (3) | 0.54225 (5) | 0.0203 (4) | |
H1W2 | 0.4460 (12) | 0.310 (4) | 0.5585 (5) | 0.024 (8)* | |
H2W2 | 0.4469 (14) | 0.300 (4) | 0.5253 (5) | 0.046 (10)* | |
O3W | 0.47153 (9) | 0.4637 (3) | 0.38524 (5) | 0.0189 (4) | |
H1W3 | 0.4493 (13) | 0.439 (4) | 0.4008 (6) | 0.039 (9)* | |
H2W3 | 0.4552 (13) | 0.417 (4) | 0.3683 (5) | 0.031 (9)* | |
N1A | 0.53728 (11) | 0.1701 (3) | 0.62582 (6) | 0.0169 (5) | |
H1AA | 0.4979 (16) | 0.123 (4) | 0.6303 (8) | 0.039 (9)* | |
H1AB | 0.5305 (15) | 0.293 (4) | 0.6212 (8) | 0.036 (9)* | |
N2A | 0.67722 (10) | 0.1578 (3) | 0.61970 (5) | 0.0153 (5) | |
C1A | 0.56652 (12) | 0.0802 (3) | 0.59424 (7) | 0.0166 (6) | |
H1AC | 0.536526 | 0.091693 | 0.572342 | 0.020* | |
H1AD | 0.573059 | −0.049571 | 0.599461 | 0.020* | |
C2A | 0.63171 (12) | 0.1678 (3) | 0.58741 (6) | 0.0155 (5) | |
H2AA | 0.651615 | 0.106930 | 0.566729 | 0.019* | |
H2AB | 0.624385 | 0.295573 | 0.580691 | 0.019* | |
C3A | 0.64855 (13) | 0.2351 (4) | 0.65186 (6) | 0.0173 (6) | |
H3A1 | 0.643210 | 0.366608 | 0.648468 | 0.021* | |
H3A2 | 0.678752 | 0.215151 | 0.673412 | 0.021* | |
C4A | 0.58240 (13) | 0.1516 (4) | 0.65859 (7) | 0.0190 (6) | |
H4AA | 0.588228 | 0.022477 | 0.664660 | 0.023* | |
H4AB | 0.563121 | 0.211922 | 0.679520 | 0.023* | |
C5A | 0.74157 (13) | 0.2193 (3) | 0.61344 (6) | 0.0150 (5) | |
C6A | 0.77415 (13) | 0.1533 (3) | 0.58374 (7) | 0.0175 (6) | |
H6A | 0.752173 | 0.070253 | 0.567695 | 0.021* | |
C7A | 0.83727 (13) | 0.2051 (3) | 0.57702 (7) | 0.0186 (6) | |
H7A | 0.857901 | 0.158525 | 0.556458 | 0.022* | |
C8A | 0.87077 (13) | 0.3250 (3) | 0.60019 (7) | 0.0172 (6) | |
C9A | 0.83902 (13) | 0.3916 (4) | 0.62985 (7) | 0.0187 (6) | |
H9A | 0.861272 | 0.473954 | 0.645926 | 0.022* | |
C10A | 0.77587 (13) | 0.3404 (3) | 0.63637 (7) | 0.0181 (6) | |
H10A | 0.755274 | 0.388262 | 0.656829 | 0.022* | |
O1A | 0.93324 (9) | 0.3865 (3) | 0.59612 (5) | 0.0246 (5) | |
C11A | 0.96791 (14) | 0.3085 (4) | 0.56715 (7) | 0.0277 (7) | |
H11A | 1.012352 | 0.358505 | 0.567375 | 0.042* | |
H11B | 0.944723 | 0.335895 | 0.543819 | 0.042* | |
H11C | 0.970366 | 0.177628 | 0.570434 | 0.042* | |
I1A | 0.07054 (2) | 0.22414 (3) | 0.65985 (2) | 0.03241 (6) | |
O2A | 0.41019 (9) | 0.0741 (2) | 0.64110 (4) | 0.0182 (4) | |
O3A | 0.38729 (10) | 0.2563 (3) | 0.59416 (5) | 0.0327 (5) | |
C12A | 0.37115 (13) | 0.1708 (3) | 0.62136 (7) | 0.0177 (6) | |
C13A | 0.30062 (13) | 0.1839 (3) | 0.63110 (6) | 0.0155 (6) | |
C14A | 0.25598 (14) | 0.2798 (3) | 0.60871 (7) | 0.0202 (6) | |
H14A | 0.270779 | 0.337633 | 0.587618 | 0.024* | |
C15A | 0.19067 (14) | 0.2927 (4) | 0.61649 (7) | 0.0235 (6) | |
H15A | 0.160641 | 0.357675 | 0.600863 | 0.028* | |
C16A | 0.16966 (13) | 0.2086 (3) | 0.64770 (7) | 0.0189 (6) | |
C17A | 0.21308 (13) | 0.1131 (3) | 0.67042 (7) | 0.0185 (6) | |
H17A | 0.198222 | 0.056099 | 0.691601 | 0.022* | |
C18A | 0.27842 (13) | 0.1008 (3) | 0.66215 (6) | 0.0150 (5) | |
H18A | 0.308316 | 0.035272 | 0.677757 | 0.018* | |
N1B | 0.54528 (11) | 0.2872 (3) | 0.46279 (6) | 0.0157 (5) | |
H1BA | 0.5047 (15) | 0.247 (4) | 0.4678 (8) | 0.032 (9)* | |
H1BB | 0.5413 (13) | 0.410 (4) | 0.4599 (7) | 0.019 (7)* | |
N2B | 0.68341 (10) | 0.2390 (3) | 0.45357 (5) | 0.0145 (5) | |
C1B | 0.57009 (12) | 0.1948 (3) | 0.43022 (6) | 0.0156 (6) | |
H1BC | 0.539379 | 0.215359 | 0.408906 | 0.019* | |
H1BD | 0.572919 | 0.063524 | 0.434700 | 0.019* | |
C2B | 0.63691 (12) | 0.2675 (3) | 0.42252 (6) | 0.0151 (5) | |
H2BA | 0.653183 | 0.206538 | 0.400822 | 0.018* | |
H2BB | 0.633515 | 0.397882 | 0.417175 | 0.018* | |
C3B | 0.66000 (12) | 0.3265 (3) | 0.48621 (6) | 0.0161 (6) | |
H3B1 | 0.658596 | 0.458500 | 0.482408 | 0.019* | |
H3B2 | 0.691065 | 0.301479 | 0.507155 | 0.019* | |
C4B | 0.59236 (13) | 0.2603 (4) | 0.49477 (6) | 0.0173 (6) | |
H4BA | 0.594522 | 0.130750 | 0.501113 | 0.021* | |
H4BB | 0.576808 | 0.326780 | 0.515985 | 0.021* | |
C5B | 0.75017 (12) | 0.2699 (3) | 0.44638 (6) | 0.0134 (5) | |
C6B | 0.77627 (13) | 0.1969 (3) | 0.41512 (7) | 0.0166 (6) | |
H6B | 0.747807 | 0.135704 | 0.398002 | 0.020* | |
C7B | 0.84192 (13) | 0.2109 (3) | 0.40838 (7) | 0.0181 (6) | |
H7B | 0.857875 | 0.160425 | 0.386830 | 0.022* | |
C8B | 0.88469 (13) | 0.2985 (3) | 0.43297 (7) | 0.0185 (6) | |
C9B | 0.85954 (13) | 0.3744 (4) | 0.46404 (7) | 0.0208 (6) | |
H9B | 0.888096 | 0.435936 | 0.481045 | 0.025* | |
C10B | 0.79355 (13) | 0.3610 (3) | 0.47032 (7) | 0.0182 (6) | |
H10B | 0.777431 | 0.415177 | 0.491472 | 0.022* | |
O1B | 0.95052 (9) | 0.3195 (3) | 0.42936 (5) | 0.0280 (5) | |
C11B | 0.97811 (14) | 0.2421 (4) | 0.39805 (8) | 0.0303 (7) | |
H11D | 1.025183 | 0.268615 | 0.398486 | 0.045* | |
H11E | 0.956558 | 0.293296 | 0.375985 | 0.045* | |
H11F | 0.971528 | 0.111410 | 0.398221 | 0.045* | |
I1B | 0.07478 (2) | 0.15453 (3) | 0.49437 (2) | 0.02872 (6) | |
O2B | 0.41837 (9) | 0.1894 (2) | 0.47849 (5) | 0.0198 (4) | |
O3B | 0.38573 (10) | 0.3743 (3) | 0.43324 (5) | 0.0298 (5) | |
C12B | 0.37472 (13) | 0.2739 (3) | 0.45938 (7) | 0.0178 (6) | |
C13B | 0.30402 (13) | 0.2499 (3) | 0.46834 (6) | 0.0145 (5) | |
C14B | 0.25389 (13) | 0.3216 (3) | 0.44580 (7) | 0.0179 (6) | |
H14B | 0.264596 | 0.389536 | 0.425054 | 0.022* | |
C15B | 0.18860 (14) | 0.2958 (4) | 0.45298 (7) | 0.0201 (6) | |
H15B | 0.154697 | 0.343937 | 0.437190 | 0.024* | |
C16B | 0.17363 (13) | 0.1985 (3) | 0.48365 (7) | 0.0186 (6) | |
C17B | 0.22246 (13) | 0.1289 (3) | 0.50692 (7) | 0.0186 (6) | |
H17B | 0.211464 | 0.064335 | 0.528047 | 0.022* | |
C18B | 0.28755 (13) | 0.1538 (3) | 0.49930 (6) | 0.0163 (6) | |
H18B | 0.321254 | 0.105354 | 0.515187 | 0.020* | |
N1C | 0.54732 (11) | 0.4096 (3) | 0.30188 (6) | 0.0151 (5) | |
H1CA | 0.5039 (15) | 0.382 (4) | 0.3092 (8) | 0.036 (9)* | |
H1CB | 0.5487 (13) | 0.519 (4) | 0.2976 (7) | 0.012 (7)* | |
N2C | 0.67789 (10) | 0.2903 (3) | 0.28952 (5) | 0.0140 (5) | |
C1C | 0.56203 (13) | 0.3023 (4) | 0.26914 (7) | 0.0183 (6) | |
H1CC | 0.531549 | 0.337052 | 0.248527 | 0.022* | |
H1CD | 0.555525 | 0.172679 | 0.274144 | 0.022* | |
C2C | 0.63187 (12) | 0.3341 (4) | 0.25908 (6) | 0.0168 (6) | |
H2CA | 0.641494 | 0.258599 | 0.237828 | 0.020* | |
H2CB | 0.637343 | 0.461852 | 0.252166 | 0.020* | |
C3C | 0.66487 (13) | 0.3992 (4) | 0.32146 (6) | 0.0164 (6) | |
H3C1 | 0.671354 | 0.528155 | 0.315826 | 0.020* | |
H3C2 | 0.696146 | 0.366146 | 0.341838 | 0.020* | |
C4C | 0.59550 (12) | 0.3697 (4) | 0.33264 (6) | 0.0164 (6) | |
H4CA | 0.590283 | 0.243214 | 0.340487 | 0.020* | |
H4CB | 0.586798 | 0.448762 | 0.353511 | 0.020* | |
C5C | 0.74472 (12) | 0.2758 (3) | 0.28062 (6) | 0.0141 (5) | |
C6C | 0.76069 (13) | 0.1706 (3) | 0.25095 (7) | 0.0177 (6) | |
H6C | 0.726496 | 0.118494 | 0.235930 | 0.021* | |
C7C | 0.82550 (13) | 0.1404 (4) | 0.24290 (7) | 0.0186 (6) | |
H7C | 0.835037 | 0.070293 | 0.222230 | 0.022* | |
C8C | 0.87656 (13) | 0.2121 (4) | 0.26487 (7) | 0.0196 (6) | |
C9C | 0.86090 (13) | 0.3184 (4) | 0.29422 (7) | 0.0204 (6) | |
H9C | 0.895187 | 0.369408 | 0.309346 | 0.025* | |
C10C | 0.79633 (13) | 0.3517 (3) | 0.30189 (7) | 0.0177 (6) | |
H10C | 0.786977 | 0.427006 | 0.321839 | 0.021* | |
O1C | 0.94180 (9) | 0.1861 (3) | 0.26005 (5) | 0.0250 (4) | |
C11C | 0.95839 (14) | 0.0599 (4) | 0.23304 (8) | 0.0314 (7) | |
H11G | 1.006183 | 0.046967 | 0.233207 | 0.047* | |
H11H | 0.941860 | 0.102414 | 0.209073 | 0.047* | |
H11I | 0.938558 | −0.056985 | 0.238193 | 0.047* | |
I1C | 0.09042 (2) | 0.06781 (3) | 0.31910 (2) | 0.03020 (6) | |
O2C | 0.42707 (9) | 0.3016 (2) | 0.32290 (5) | 0.0202 (4) | |
O3C | 0.39400 (9) | 0.4141 (2) | 0.26896 (5) | 0.0235 (4) | |
C12C | 0.38327 (13) | 0.3315 (3) | 0.29758 (7) | 0.0167 (6) | |
C13C | 0.31525 (13) | 0.2627 (3) | 0.30286 (7) | 0.0155 (6) | |
C14C | 0.27202 (13) | 0.2325 (4) | 0.27301 (7) | 0.0192 (6) | |
H14C | 0.286224 | 0.254050 | 0.249216 | 0.023* | |
C15C | 0.20884 (14) | 0.1719 (4) | 0.27722 (7) | 0.0212 (6) | |
H15C | 0.180102 | 0.148483 | 0.256620 | 0.025* | |
C16C | 0.18836 (13) | 0.1459 (3) | 0.31218 (7) | 0.0198 (6) | |
C17C | 0.23004 (13) | 0.1737 (3) | 0.34227 (7) | 0.0204 (6) | |
H17C | 0.215262 | 0.154375 | 0.366023 | 0.024* | |
C18C | 0.29359 (13) | 0.2299 (3) | 0.33759 (7) | 0.0172 (6) | |
H18C | 0.322853 | 0.246385 | 0.358253 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1W | 0.0265 (12) | 0.0229 (11) | 0.0167 (10) | −0.0040 (9) | −0.0009 (9) | −0.0004 (9) |
O2W | 0.0214 (11) | 0.0235 (11) | 0.0165 (10) | −0.0031 (9) | 0.0052 (9) | 0.0010 (9) |
O3W | 0.0203 (11) | 0.0206 (11) | 0.0162 (10) | −0.0003 (9) | 0.0046 (9) | −0.0003 (9) |
N1A | 0.0159 (13) | 0.0171 (12) | 0.0181 (11) | −0.0011 (10) | 0.0039 (9) | 0.0005 (10) |
N2A | 0.0131 (11) | 0.0181 (11) | 0.0149 (10) | −0.0004 (9) | 0.0023 (9) | −0.0008 (9) |
C1A | 0.0151 (14) | 0.0154 (13) | 0.0195 (13) | 0.0004 (11) | 0.0023 (11) | −0.0022 (11) |
C2A | 0.0143 (14) | 0.0174 (13) | 0.0148 (12) | −0.0001 (11) | 0.0021 (10) | −0.0003 (11) |
C3A | 0.0176 (14) | 0.0226 (14) | 0.0118 (12) | 0.0011 (12) | 0.0027 (10) | −0.0008 (11) |
C4A | 0.0172 (14) | 0.0234 (15) | 0.0169 (13) | 0.0007 (12) | 0.0045 (11) | 0.0036 (11) |
C5A | 0.0144 (14) | 0.0156 (13) | 0.0151 (12) | 0.0021 (11) | 0.002 (1) | 0.002 (1) |
C6A | 0.0169 (14) | 0.0176 (14) | 0.0178 (13) | −0.0018 (11) | 0.0005 (11) | −0.0041 (11) |
C7A | 0.0190 (15) | 0.0186 (14) | 0.0184 (13) | −0.0003 (12) | 0.0037 (11) | −0.0044 (11) |
C8A | 0.0135 (14) | 0.0154 (13) | 0.0227 (13) | 0.0011 (11) | 0.0023 (11) | 0.0019 (11) |
C9A | 0.0188 (15) | 0.0187 (14) | 0.0184 (13) | −0.0014 (12) | −0.0022 (11) | −0.0046 (11) |
C10A | 0.0192 (15) | 0.0209 (14) | 0.0144 (12) | 0.0023 (12) | 0.0023 (11) | −0.0048 (11) |
O1A | 0.0158 (10) | 0.0288 (11) | 0.0298 (11) | −0.0064 (9) | 0.0071 (8) | −0.0099 (9) |
C11A | 0.0202 (16) | 0.0354 (18) | 0.0285 (15) | −0.0036 (14) | 0.0106 (13) | −0.0057 (13) |
I1A | 0.01674 (11) | 0.02892 (11) | 0.05171 (13) | 0.00099 (9) | 0.00330 (9) | −0.01156 (10) |
O2A | 0.0175 (10) | 0.0203 (10) | 0.0172 (9) | −0.0023 (8) | 0.0037 (8) | −0.0022 (8) |
O3A | 0.0343 (13) | 0.0381 (13) | 0.0272 (11) | −0.0018 (10) | 0.0153 (10) | 0.0115 (9) |
C12A | 0.0219 (15) | 0.0157 (13) | 0.0161 (13) | −0.0048 (12) | 0.0049 (11) | −0.0050 (11) |
C13A | 0.0187 (14) | 0.0117 (13) | 0.0163 (12) | −0.0049 (11) | 0.0036 (11) | −0.0033 (10) |
C14A | 0.0309 (17) | 0.0133 (13) | 0.0165 (13) | −0.0043 (12) | 0.0016 (12) | 0.0018 (11) |
C15A | 0.0240 (16) | 0.0169 (14) | 0.0289 (15) | 0.0013 (12) | −0.0063 (13) | −0.0009 (12) |
C16A | 0.0144 (14) | 0.0157 (13) | 0.0266 (14) | −0.0033 (11) | 0.0008 (11) | −0.0078 (11) |
C17A | 0.0194 (15) | 0.0163 (13) | 0.0202 (13) | −0.0021 (12) | 0.0054 (11) | 0.0001 (11) |
C18A | 0.0183 (14) | 0.0118 (12) | 0.0150 (12) | −0.0017 (11) | 0.0014 (10) | −0.0003 (10) |
N1B | 0.0149 (12) | 0.0150 (12) | 0.0173 (11) | −0.0009 (10) | 0.0026 (9) | −0.0006 (9) |
N2B | 0.0153 (12) | 0.0160 (11) | 0.0122 (10) | −0.0009 (9) | 0.0012 (9) | −0.0021 (9) |
C1B | 0.0146 (14) | 0.0169 (13) | 0.0156 (12) | −0.0003 (11) | 0.0018 (10) | −0.0011 (10) |
C2B | 0.0160 (14) | 0.0181 (13) | 0.0112 (12) | 0.0007 (11) | 0.0017 (10) | −0.0018 (10) |
C3B | 0.0172 (14) | 0.0200 (14) | 0.0113 (12) | −0.0013 (11) | 0.0015 (10) | −0.002 (1) |
C4B | 0.0186 (14) | 0.0197 (14) | 0.0137 (12) | −0.0005 (12) | 0.0018 (11) | 0.0003 (11) |
C5B | 0.0164 (14) | 0.0098 (12) | 0.0137 (12) | 0.0006 (11) | −0.0013 (10) | 0.0015 (10) |
C6B | 0.0187 (14) | 0.0145 (13) | 0.0163 (13) | −0.0023 (11) | −0.0005 (11) | −0.0029 (10) |
C7B | 0.0201 (15) | 0.0158 (13) | 0.0186 (13) | −0.0015 (12) | 0.0026 (11) | −0.0044 (11) |
C8B | 0.0141 (14) | 0.0169 (14) | 0.0247 (14) | 0.0006 (11) | 0.0020 (11) | 0.0000 (11) |
C9B | 0.0206 (15) | 0.0222 (15) | 0.0193 (13) | −0.0040 (12) | −0.0032 (11) | −0.0065 (11) |
C10B | 0.0218 (15) | 0.0182 (14) | 0.0147 (12) | 0.0024 (12) | 0.0019 (11) | −0.0032 (11) |
O1B | 0.0137 (10) | 0.0354 (12) | 0.0351 (11) | −0.0036 (9) | 0.0042 (9) | −0.0124 (9) |
C11B | 0.0209 (16) | 0.0357 (18) | 0.0352 (17) | −0.0038 (14) | 0.0105 (13) | −0.0099 (14) |
I1B | 0.01675 (10) | 0.02811 (11) | 0.04205 (12) | −0.00272 (8) | 0.00875 (8) | −0.00998 (9) |
O2B | 0.0172 (10) | 0.0225 (10) | 0.0201 (9) | −0.0013 (8) | 0.0046 (8) | −0.0032 (8) |
O3B | 0.0288 (12) | 0.0302 (12) | 0.0318 (11) | −0.0017 (10) | 0.0138 (9) | 0.0118 (9) |
C12B | 0.0227 (15) | 0.0143 (13) | 0.0168 (13) | −0.0043 (12) | 0.0061 (11) | −0.0069 (11) |
C13B | 0.0195 (14) | 0.0099 (12) | 0.0142 (12) | −0.0023 (11) | 0.0042 (11) | −0.0035 (10) |
C14B | 0.0244 (15) | 0.0155 (13) | 0.0139 (12) | −0.0051 (12) | 0.0003 (11) | −0.0001 (10) |
C15B | 0.0212 (15) | 0.0175 (14) | 0.0212 (14) | −0.0001 (12) | −0.0036 (11) | −0.0016 (11) |
C16B | 0.0151 (14) | 0.0159 (13) | 0.0254 (14) | −0.0006 (11) | 0.0063 (11) | −0.0054 (11) |
C17B | 0.0226 (15) | 0.0139 (13) | 0.0200 (13) | −0.0004 (12) | 0.0078 (11) | 0.0017 (11) |
C18B | 0.0193 (14) | 0.0153 (13) | 0.0143 (12) | 0.0017 (11) | 0.0020 (11) | 0.0010 (11) |
N1C | 0.0162 (13) | 0.0145 (12) | 0.0147 (11) | −0.0014 (10) | 0.0001 (9) | 0.0002 (9) |
N2C | 0.0143 (11) | 0.0166 (11) | 0.0111 (10) | 0.0006 (9) | 0.0010 (9) | −0.0015 (8) |
C1C | 0.0172 (14) | 0.0209 (14) | 0.0169 (13) | 0.0001 (12) | 0.0005 (11) | −0.0040 (11) |
C2C | 0.0158 (14) | 0.0212 (14) | 0.0132 (12) | 0.0010 (11) | −0.0005 (10) | −0.0002 (11) |
C3C | 0.0177 (14) | 0.0198 (14) | 0.0116 (12) | 0.0000 (11) | 0.0003 (10) | −0.0012 (10) |
C4C | 0.0195 (14) | 0.0181 (14) | 0.0116 (12) | 0.0016 (12) | 0.0002 (10) | 0.0009 (10) |
C5C | 0.0149 (14) | 0.0127 (12) | 0.0146 (12) | −0.0019 (11) | 0.0001 (10) | 0.0027 (10) |
C6C | 0.0163 (14) | 0.0201 (14) | 0.0166 (13) | −0.0025 (12) | −0.0015 (11) | −0.0024 (11) |
C7C | 0.0173 (14) | 0.0208 (14) | 0.0182 (13) | 0.0001 (12) | 0.0038 (11) | −0.0027 (11) |
C8C | 0.0181 (15) | 0.0165 (13) | 0.0245 (14) | −0.0009 (12) | 0.0045 (12) | 0.0057 (11) |
C9C | 0.0190 (15) | 0.0197 (14) | 0.0222 (14) | −0.0047 (12) | −0.0031 (11) | −0.0014 (11) |
C10C | 0.0213 (15) | 0.0135 (13) | 0.0183 (13) | −0.0012 (12) | 0.0006 (11) | −0.0013 (11) |
O1C | 0.0143 (10) | 0.0282 (11) | 0.0330 (11) | −0.0004 (9) | 0.0054 (8) | −0.0037 (9) |
C11C | 0.0221 (17) | 0.0376 (18) | 0.0352 (17) | 0.0049 (14) | 0.0083 (13) | −0.0043 (15) |
I1C | 0.01743 (10) | 0.02945 (11) | 0.04390 (12) | −0.00327 (8) | 0.00347 (8) | −0.00136 (9) |
O2C | 0.0165 (10) | 0.0249 (11) | 0.0194 (9) | −0.0022 (8) | 0.0017 (8) | 0.0013 (8) |
O3C | 0.0266 (11) | 0.0239 (10) | 0.0208 (10) | 0.0009 (9) | 0.0075 (8) | 0.0070 (8) |
C12C | 0.0204 (15) | 0.0119 (13) | 0.0184 (13) | 0.0016 (11) | 0.0061 (11) | −0.0043 (11) |
C13C | 0.0203 (15) | 0.0090 (12) | 0.0175 (13) | 0.0026 (11) | 0.0026 (11) | −0.0012 (10) |
C14C | 0.0201 (15) | 0.0206 (14) | 0.0172 (13) | 0.0042 (12) | 0.0030 (11) | −0.0018 (11) |
C15C | 0.0216 (15) | 0.0200 (14) | 0.0215 (14) | 0.0033 (12) | −0.0030 (12) | −0.0060 (12) |
C16C | 0.0134 (14) | 0.0149 (13) | 0.0311 (15) | 0.0027 (11) | 0.0031 (12) | −0.0010 (12) |
C17C | 0.0224 (15) | 0.0179 (14) | 0.0213 (13) | 0.0026 (12) | 0.0050 (12) | 0.0033 (11) |
C18C | 0.0188 (15) | 0.0160 (13) | 0.0168 (13) | 0.0009 (11) | 0.0001 (11) | 0.0013 (11) |
O1W—H1W1 | 0.769 (15) | C6B—H6B | 0.9500 |
O1W—H2W1 | 0.768 (15) | C7B—C8B | 1.386 (4) |
O2W—H1W2 | 0.770 (14) | C7B—H7B | 0.9500 |
O2W—H2W2 | 0.774 (15) | C8B—O1B | 1.366 (3) |
O3W—H1W3 | 0.771 (15) | C8B—C9B | 1.396 (3) |
O3W—H2W3 | 0.775 (14) | C9B—C10B | 1.382 (4) |
N1A—C4A | 1.486 (3) | C9B—H9B | 0.9500 |
N1A—C1A | 1.491 (3) | C10B—H10B | 0.9500 |
N1A—H1AA | 0.90 (3) | O1B—C11B | 1.429 (3) |
N1A—H1AB | 0.94 (3) | C11B—H11D | 0.9800 |
N2A—C5A | 1.421 (3) | C11B—H11E | 0.9800 |
N2A—C3A | 1.464 (3) | C11B—H11F | 0.9800 |
N2A—C2A | 1.472 (3) | I1B—C16B | 2.101 (3) |
C1A—C2A | 1.514 (3) | O2B—C12B | 1.272 (3) |
C1A—H1AC | 0.9900 | O3B—C12B | 1.246 (3) |
C1A—H1AD | 0.9900 | C12B—C13B | 1.507 (3) |
C2A—H2AA | 0.9900 | C13B—C14B | 1.389 (4) |
C2A—H2AB | 0.9900 | C13B—C18B | 1.400 (3) |
C3A—C4A | 1.518 (3) | C14B—C15B | 1.385 (4) |
C3A—H3A1 | 0.9900 | C14B—H14B | 0.9500 |
C3A—H3A2 | 0.9900 | C15B—C16B | 1.388 (4) |
C4A—H4AA | 0.9900 | C15B—H15B | 0.9500 |
C4A—H4AB | 0.9900 | C16B—C17B | 1.380 (4) |
C5A—C10A | 1.396 (4) | C17B—C18B | 1.384 (3) |
C5A—C6A | 1.397 (3) | C17B—H17B | 0.9500 |
C6A—C7A | 1.379 (3) | C18B—H18B | 0.9500 |
C6A—H6A | 0.9500 | N1C—C1C | 1.488 (3) |
C7A—C8A | 1.388 (4) | N1C—C4C | 1.490 (3) |
C7A—H7A | 0.9500 | N1C—H1CA | 0.96 (3) |
C8A—O1A | 1.370 (3) | N1C—H1CB | 0.83 (3) |
C8A—C9A | 1.389 (3) | N2C—C5C | 1.424 (3) |
C9A—C10A | 1.377 (4) | N2C—C2C | 1.461 (3) |
C9A—H9A | 0.9500 | N2C—C3C | 1.462 (3) |
C10A—H10A | 0.9500 | C1C—C2C | 1.510 (3) |
O1A—C11A | 1.432 (3) | C1C—H1CC | 0.9900 |
C11A—H11A | 0.9800 | C1C—H1CD | 0.9900 |
C11A—H11B | 0.9800 | C2C—H2CA | 0.9900 |
C11A—H11C | 0.9800 | C2C—H2CB | 0.9900 |
I1A—C16A | 2.098 (3) | C3C—C4C | 1.511 (3) |
O2A—C12A | 1.272 (3) | C3C—H3C1 | 0.9900 |
O3A—C12A | 1.244 (3) | C3C—H3C2 | 0.9900 |
C12A—C13A | 1.505 (3) | C4C—H4CA | 0.9900 |
C13A—C14A | 1.392 (4) | C4C—H4CB | 0.9900 |
C13A—C18A | 1.394 (3) | C5C—C6C | 1.395 (3) |
C14A—C15A | 1.381 (4) | C5C—C10C | 1.398 (4) |
C14A—H14A | 0.9500 | C6C—C7C | 1.389 (3) |
C15A—C16A | 1.394 (4) | C6C—H6C | 0.9500 |
C15A—H15A | 0.9500 | C7C—C8C | 1.392 (4) |
C16A—C17A | 1.383 (4) | C7C—H7C | 0.9500 |
C17A—C18A | 1.386 (3) | C8C—O1C | 1.366 (3) |
C17A—H17A | 0.9500 | C8C—C9C | 1.388 (4) |
C18A—H18A | 0.9500 | C9C—C10C | 1.384 (4) |
N1B—C1B | 1.492 (3) | C9C—H9C | 0.9500 |
N1B—C4B | 1.494 (3) | C10C—H10C | 0.9500 |
N1B—H1BA | 0.91 (3) | O1C—C11C | 1.420 (3) |
N1B—H1BB | 0.92 (3) | C11C—H11G | 0.9800 |
N2B—C5B | 1.420 (3) | C11C—H11H | 0.9800 |
N2B—C2B | 1.462 (3) | C11C—H11I | 0.9800 |
N2B—C3B | 1.467 (3) | I1C—C16C | 2.110 (3) |
C1B—C2B | 1.507 (3) | O2C—C12C | 1.277 (3) |
C1B—H1BC | 0.9900 | O3C—C12C | 1.248 (3) |
C1B—H1BD | 0.9900 | C12C—C13C | 1.501 (4) |
C2B—H2BA | 0.9900 | C13C—C14C | 1.391 (4) |
C2B—H2BB | 0.9900 | C13C—C18C | 1.395 (3) |
C3B—C4B | 1.514 (3) | C14C—C15C | 1.382 (4) |
C3B—H3B1 | 0.9900 | C14C—H14C | 0.9500 |
C3B—H3B2 | 0.9900 | C15C—C16C | 1.387 (3) |
C4B—H4BA | 0.9900 | C15C—H15C | 0.9500 |
C4B—H4BB | 0.9900 | C16C—C17C | 1.376 (4) |
C5B—C10B | 1.392 (4) | C17C—C18C | 1.382 (4) |
C5B—C6B | 1.402 (3) | C17C—H17C | 0.9500 |
C6B—C7B | 1.379 (3) | C18C—H18C | 0.9500 |
H1W1—O1W—H2W1 | 106 (2) | C5B—C6B—H6B | 118.9 |
H1W2—O2W—H2W2 | 105 (2) | C6B—C7B—C8B | 120.2 (2) |
H1W3—O3W—H2W3 | 104 (2) | C6B—C7B—H7B | 119.9 |
C4A—N1A—C1A | 109.6 (2) | C8B—C7B—H7B | 119.9 |
C4A—N1A—H1AA | 110 (2) | O1B—C8B—C7B | 125.4 (2) |
C1A—N1A—H1AA | 111 (2) | O1B—C8B—C9B | 116.0 (2) |
C4A—N1A—H1AB | 108.4 (19) | C7B—C8B—C9B | 118.6 (2) |
C1A—N1A—H1AB | 110.9 (18) | C10B—C9B—C8B | 120.7 (2) |
H1AA—N1A—H1AB | 107 (3) | C10B—C9B—H9B | 119.6 |
C5A—N2A—C3A | 114.6 (2) | C8B—C9B—H9B | 119.6 |
C5A—N2A—C2A | 113.78 (19) | C9B—C10B—C5B | 121.5 (2) |
C3A—N2A—C2A | 111.8 (2) | C9B—C10B—H10B | 119.2 |
N1A—C1A—C2A | 109.1 (2) | C5B—C10B—H10B | 119.2 |
N1A—C1A—H1AC | 109.9 | C8B—O1B—C11B | 117.6 (2) |
C2A—C1A—H1AC | 109.9 | O1B—C11B—H11D | 109.5 |
N1A—C1A—H1AD | 109.9 | O1B—C11B—H11E | 109.5 |
C2A—C1A—H1AD | 109.9 | H11D—C11B—H11E | 109.5 |
H1AC—C1A—H1AD | 108.3 | O1B—C11B—H11F | 109.5 |
N2A—C2A—C1A | 111.6 (2) | H11D—C11B—H11F | 109.5 |
N2A—C2A—H2AA | 109.3 | H11E—C11B—H11F | 109.5 |
C1A—C2A—H2AA | 109.3 | O3B—C12B—O2B | 124.9 (2) |
N2A—C2A—H2AB | 109.3 | O3B—C12B—C13B | 116.9 (2) |
C1A—C2A—H2AB | 109.3 | O2B—C12B—C13B | 118.1 (2) |
H2AA—C2A—H2AB | 108.0 | C14B—C13B—C18B | 118.7 (2) |
N2A—C3A—C4A | 111.6 (2) | C14B—C13B—C12B | 120.5 (2) |
N2A—C3A—H3A1 | 109.3 | C18B—C13B—C12B | 120.8 (2) |
C4A—C3A—H3A1 | 109.3 | C15B—C14B—C13B | 121.3 (2) |
N2A—C3A—H3A2 | 109.3 | C15B—C14B—H14B | 119.4 |
C4A—C3A—H3A2 | 109.3 | C13B—C14B—H14B | 119.4 |
H3A1—C3A—H3A2 | 108.0 | C14B—C15B—C16B | 118.8 (3) |
N1A—C4A—C3A | 110.4 (2) | C14B—C15B—H15B | 120.6 |
N1A—C4A—H4AA | 109.6 | C16B—C15B—H15B | 120.6 |
C3A—C4A—H4AA | 109.6 | C17B—C16B—C15B | 121.1 (2) |
N1A—C4A—H4AB | 109.6 | C17B—C16B—I1B | 119.67 (18) |
C3A—C4A—H4AB | 109.6 | C15B—C16B—I1B | 119.2 (2) |
H4AA—C4A—H4AB | 108.1 | C16B—C17B—C18B | 119.6 (2) |
C10A—C5A—C6A | 117.0 (2) | C16B—C17B—H17B | 120.2 |
C10A—C5A—N2A | 123.2 (2) | C18B—C17B—H17B | 120.2 |
C6A—C5A—N2A | 119.7 (2) | C17B—C18B—C13B | 120.4 (3) |
C7A—C6A—C5A | 122.0 (2) | C17B—C18B—H18B | 119.8 |
C7A—C6A—H6A | 119.0 | C13B—C18B—H18B | 119.8 |
C5A—C6A—H6A | 119.0 | C1C—N1C—C4C | 110.8 (2) |
C6A—C7A—C8A | 120.3 (2) | C1C—N1C—H1CA | 110.1 (18) |
C6A—C7A—H7A | 119.9 | C4C—N1C—H1CA | 109.0 (18) |
C8A—C7A—H7A | 119.9 | C1C—N1C—H1CB | 111.1 (17) |
O1A—C8A—C7A | 125.3 (2) | C4C—N1C—H1CB | 108.2 (19) |
O1A—C8A—C9A | 116.2 (2) | H1CA—N1C—H1CB | 108 (3) |
C7A—C8A—C9A | 118.4 (2) | C5C—N2C—C2C | 115.22 (19) |
C10A—C9A—C8A | 121.2 (2) | C5C—N2C—C3C | 116.3 (2) |
C10A—C9A—H9A | 119.4 | C2C—N2C—C3C | 110.9 (2) |
C8A—C9A—H9A | 119.4 | N1C—C1C—C2C | 110.3 (2) |
C9A—C10A—C5A | 121.1 (2) | N1C—C1C—H1CC | 109.6 |
C9A—C10A—H10A | 119.4 | C2C—C1C—H1CC | 109.6 |
C5A—C10A—H10A | 119.4 | N1C—C1C—H1CD | 109.6 |
C8A—O1A—C11A | 116.4 (2) | C2C—C1C—H1CD | 109.6 |
O1A—C11A—H11A | 109.5 | H1CC—C1C—H1CD | 108.1 |
O1A—C11A—H11B | 109.5 | N2C—C2C—C1C | 110.8 (2) |
H11A—C11A—H11B | 109.5 | N2C—C2C—H2CA | 109.5 |
O1A—C11A—H11C | 109.5 | C1C—C2C—H2CA | 109.5 |
H11A—C11A—H11C | 109.5 | N2C—C2C—H2CB | 109.5 |
H11B—C11A—H11C | 109.5 | C1C—C2C—H2CB | 109.5 |
O3A—C12A—O2A | 124.3 (2) | H2CA—C2C—H2CB | 108.1 |
O3A—C12A—C13A | 117.1 (2) | N2C—C3C—C4C | 110.5 (2) |
O2A—C12A—C13A | 118.6 (2) | N2C—C3C—H3C1 | 109.5 |
C14A—C13A—C18A | 118.7 (2) | C4C—C3C—H3C1 | 109.5 |
C14A—C13A—C12A | 119.8 (2) | N2C—C3C—H3C2 | 109.5 |
C18A—C13A—C12A | 121.5 (2) | C4C—C3C—H3C2 | 109.5 |
C15A—C14A—C13A | 121.5 (2) | H3C1—C3C—H3C2 | 108.1 |
C15A—C14A—H14A | 119.3 | N1C—C4C—C3C | 110.8 (2) |
C13A—C14A—H14A | 119.3 | N1C—C4C—H4CA | 109.5 |
C14A—C15A—C16A | 118.7 (3) | C3C—C4C—H4CA | 109.5 |
C14A—C15A—H15A | 120.6 | N1C—C4C—H4CB | 109.5 |
C16A—C15A—H15A | 120.6 | C3C—C4C—H4CB | 109.5 |
C17A—C16A—C15A | 120.9 (2) | H4CA—C4C—H4CB | 108.1 |
C17A—C16A—I1A | 119.64 (19) | C6C—C5C—C10C | 117.7 (2) |
C15A—C16A—I1A | 119.5 (2) | C6C—C5C—N2C | 119.2 (2) |
C16A—C17A—C18A | 119.7 (2) | C10C—C5C—N2C | 123.0 (2) |
C16A—C17A—H17A | 120.2 | C7C—C6C—C5C | 121.4 (2) |
C18A—C17A—H17A | 120.2 | C7C—C6C—H6C | 119.3 |
C17A—C18A—C13A | 120.5 (2) | C5C—C6C—H6C | 119.3 |
C17A—C18A—H18A | 119.7 | C6C—C7C—C8C | 120.5 (2) |
C13A—C18A—H18A | 119.7 | C6C—C7C—H7C | 119.8 |
C1B—N1B—C4B | 109.9 (2) | C8C—C7C—H7C | 119.8 |
C1B—N1B—H1BA | 111.2 (18) | O1C—C8C—C9C | 116.5 (2) |
C4B—N1B—H1BA | 110.7 (18) | O1C—C8C—C7C | 125.2 (2) |
C1B—N1B—H1BB | 113.3 (16) | C9C—C8C—C7C | 118.3 (2) |
C4B—N1B—H1BB | 105.8 (17) | C10C—C9C—C8C | 121.3 (3) |
H1BA—N1B—H1BB | 106 (2) | C10C—C9C—H9C | 119.3 |
C5B—N2B—C2B | 114.91 (19) | C8C—C9C—H9C | 119.3 |
C5B—N2B—C3B | 115.9 (2) | C9C—C10C—C5C | 120.8 (2) |
C2B—N2B—C3B | 110.5 (2) | C9C—C10C—H10C | 119.6 |
N1B—C1B—C2B | 109.5 (2) | C5C—C10C—H10C | 119.6 |
N1B—C1B—H1BC | 109.8 | C8C—O1C—C11C | 117.0 (2) |
C2B—C1B—H1BC | 109.8 | O1C—C11C—H11G | 109.5 |
N1B—C1B—H1BD | 109.8 | O1C—C11C—H11H | 109.5 |
C2B—C1B—H1BD | 109.8 | H11G—C11C—H11H | 109.5 |
H1BC—C1B—H1BD | 108.2 | O1C—C11C—H11I | 109.5 |
N2B—C2B—C1B | 111.0 (2) | H11G—C11C—H11I | 109.5 |
N2B—C2B—H2BA | 109.4 | H11H—C11C—H11I | 109.5 |
C1B—C2B—H2BA | 109.4 | O3C—C12C—O2C | 123.7 (2) |
N2B—C2B—H2BB | 109.4 | O3C—C12C—C13C | 118.7 (2) |
C1B—C2B—H2BB | 109.4 | O2C—C12C—C13C | 117.6 (2) |
H2BA—C2B—H2BB | 108.0 | C14C—C13C—C18C | 118.5 (2) |
N2B—C3B—C4B | 111.4 (2) | C14C—C13C—C12C | 120.4 (2) |
N2B—C3B—H3B1 | 109.3 | C18C—C13C—C12C | 121.1 (2) |
C4B—C3B—H3B1 | 109.3 | C15C—C14C—C13C | 121.4 (2) |
N2B—C3B—H3B2 | 109.3 | C15C—C14C—H14C | 119.3 |
C4B—C3B—H3B2 | 109.3 | C13C—C14C—H14C | 119.3 |
H3B1—C3B—H3B2 | 108.0 | C14C—C15C—C16C | 118.5 (3) |
N1B—C4B—C3B | 110.4 (2) | C14C—C15C—H15C | 120.8 |
N1B—C4B—H4BA | 109.6 | C16C—C15C—H15C | 120.8 |
C3B—C4B—H4BA | 109.6 | C17C—C16C—C15C | 121.5 (3) |
N1B—C4B—H4BB | 109.6 | C17C—C16C—I1C | 119.61 (19) |
C3B—C4B—H4BB | 109.6 | C15C—C16C—I1C | 118.9 (2) |
H4BA—C4B—H4BB | 108.1 | C16C—C17C—C18C | 119.3 (2) |
C10B—C5B—C6B | 116.8 (2) | C16C—C17C—H17C | 120.3 |
C10B—C5B—N2B | 123.1 (2) | C18C—C17C—H17C | 120.3 |
C6B—C5B—N2B | 120.0 (2) | C17C—C18C—C13C | 120.7 (3) |
C7B—C6B—C5B | 122.2 (2) | C17C—C18C—H18C | 119.6 |
C7B—C6B—H6B | 118.9 | C13C—C18C—H18C | 119.6 |
C4A—N1A—C1A—C2A | −59.7 (3) | C8B—C9B—C10B—C5B | 0.9 (4) |
C5A—N2A—C2A—C1A | 173.1 (2) | C6B—C5B—C10B—C9B | −1.7 (4) |
C3A—N2A—C2A—C1A | −55.1 (3) | N2B—C5B—C10B—C9B | 174.0 (2) |
N1A—C1A—C2A—N2A | 58.0 (3) | C7B—C8B—O1B—C11B | −1.3 (4) |
C5A—N2A—C3A—C4A | −175.2 (2) | C9B—C8B—O1B—C11B | 179.4 (2) |
C2A—N2A—C3A—C4A | 53.5 (3) | O3B—C12B—C13B—C14B | 6.7 (4) |
C1A—N1A—C4A—C3A | 58.9 (3) | O2B—C12B—C13B—C14B | −172.3 (2) |
N2A—C3A—C4A—N1A | −55.7 (3) | O3B—C12B—C13B—C18B | −173.8 (2) |
C3A—N2A—C5A—C10A | 1.4 (3) | O2B—C12B—C13B—C18B | 7.1 (3) |
C2A—N2A—C5A—C10A | 131.8 (3) | C18B—C13B—C14B—C15B | −1.6 (4) |
C3A—N2A—C5A—C6A | 179.3 (2) | C12B—C13B—C14B—C15B | 177.9 (2) |
C2A—N2A—C5A—C6A | −50.3 (3) | C13B—C14B—C15B—C16B | 0.9 (4) |
C10A—C5A—C6A—C7A | −0.3 (4) | C14B—C15B—C16B—C17B | 0.4 (4) |
N2A—C5A—C6A—C7A | −178.3 (2) | C14B—C15B—C16B—I1B | −178.92 (18) |
C5A—C6A—C7A—C8A | 0.6 (4) | C15B—C16B—C17B—C18B | −1.1 (4) |
C6A—C7A—C8A—O1A | −179.6 (2) | I1B—C16B—C17B—C18B | 178.25 (19) |
C6A—C7A—C8A—C9A | −0.5 (4) | C16B—C17B—C18B—C13B | 0.4 (4) |
O1A—C8A—C9A—C10A | 179.3 (2) | C14B—C13B—C18B—C17B | 0.9 (4) |
C7A—C8A—C9A—C10A | 0.1 (4) | C12B—C13B—C18B—C17B | −178.6 (2) |
C8A—C9A—C10A—C5A | 0.2 (4) | C4C—N1C—C1C—C2C | −55.2 (3) |
C6A—C5A—C10A—C9A | −0.1 (4) | C5C—N2C—C2C—C1C | 166.3 (2) |
N2A—C5A—C10A—C9A | 177.8 (2) | C3C—N2C—C2C—C1C | −59.0 (3) |
C7A—C8A—O1A—C11A | −5.2 (4) | N1C—C1C—C2C—N2C | 57.1 (3) |
C9A—C8A—O1A—C11A | 175.6 (2) | C5C—N2C—C3C—C4C | −167.4 (2) |
O3A—C12A—C13A—C14A | 3.8 (4) | C2C—N2C—C3C—C4C | 58.4 (3) |
O2A—C12A—C13A—C14A | −176.1 (2) | C1C—N1C—C4C—C3C | 55.1 (3) |
O3A—C12A—C13A—C18A | −176.6 (2) | N2C—C3C—C4C—N1C | −56.4 (3) |
O2A—C12A—C13A—C18A | 3.5 (4) | C2C—N2C—C5C—C6C | −49.1 (3) |
C18A—C13A—C14A—C15A | −0.5 (4) | C3C—N2C—C5C—C6C | 178.6 (2) |
C12A—C13A—C14A—C15A | 179.1 (2) | C2C—N2C—C5C—C10C | 135.7 (2) |
C13A—C14A—C15A—C16A | 0.6 (4) | C3C—N2C—C5C—C10C | 3.5 (3) |
C14A—C15A—C16A—C17A | −0.4 (4) | C10C—C5C—C6C—C7C | 0.6 (4) |
C14A—C15A—C16A—I1A | −179.42 (19) | N2C—C5C—C6C—C7C | −174.8 (2) |
C15A—C16A—C17A—C18A | 0.1 (4) | C5C—C6C—C7C—C8C | 1.3 (4) |
I1A—C16A—C17A—C18A | 179.17 (19) | C6C—C7C—C8C—O1C | 177.9 (2) |
C16A—C17A—C18A—C13A | −0.1 (4) | C6C—C7C—C8C—C9C | −1.9 (4) |
C14A—C13A—C18A—C17A | 0.3 (4) | O1C—C8C—C9C—C10C | −179.2 (2) |
C12A—C13A—C18A—C17A | −179.3 (2) | C7C—C8C—C9C—C10C | 0.6 (4) |
C4B—N1B—C1B—C2B | −58.0 (3) | C8C—C9C—C10C—C5C | 1.3 (4) |
C5B—N2B—C2B—C1B | 168.0 (2) | C6C—C5C—C10C—C9C | −1.9 (4) |
C3B—N2B—C2B—C1B | −58.5 (3) | N2C—C5C—C10C—C9C | 173.3 (2) |
N1B—C1B—C2B—N2B | 59.4 (3) | C9C—C8C—O1C—C11C | 172.3 (2) |
C5B—N2B—C3B—C4B | −170.5 (2) | C7C—C8C—O1C—C11C | −7.6 (4) |
C2B—N2B—C3B—C4B | 56.6 (3) | O3C—C12C—C13C—C14C | 22.7 (4) |
C1B—N1B—C4B—C3B | 56.4 (3) | O2C—C12C—C13C—C14C | −157.3 (2) |
N2B—C3B—C4B—N1B | −55.9 (3) | O3C—C12C—C13C—C18C | −156.5 (2) |
C2B—N2B—C5B—C10B | 137.5 (2) | O2C—C12C—C13C—C18C | 23.6 (3) |
C3B—N2B—C5B—C10B | 6.6 (3) | C18C—C13C—C14C—C15C | 0.2 (4) |
C2B—N2B—C5B—C6B | −46.9 (3) | C12C—C13C—C14C—C15C | −179.0 (2) |
C3B—N2B—C5B—C6B | −177.8 (2) | C13C—C14C—C15C—C16C | 1.8 (4) |
C10B—C5B—C6B—C7B | 1.1 (4) | C14C—C15C—C16C—C17C | −2.1 (4) |
N2B—C5B—C6B—C7B | −174.8 (2) | C14C—C15C—C16C—I1C | 176.51 (19) |
C5B—C6B—C7B—C8B | 0.4 (4) | C15C—C16C—C17C—C18C | 0.5 (4) |
C6B—C7B—C8B—O1B | 179.5 (2) | I1C—C16C—C17C—C18C | −178.12 (19) |
C6B—C7B—C8B—C9B | −1.3 (4) | C16C—C17C—C18C—C13C | 1.5 (4) |
O1B—C8B—C9B—C10B | 180.0 (2) | C14C—C13C—C18C—C17C | −1.8 (4) |
C7B—C8B—C9B—C10B | 0.6 (4) | C12C—C13C—C18C—C17C | 177.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3Ci | 0.77 (2) | 1.93 (2) | 2.696 (3) | 173 (3) |
O1W—H2W1···O2A | 0.77 (2) | 1.96 (2) | 2.700 (3) | 162 (3) |
O2W—H1W2···O3A | 0.77 (1) | 1.86 (2) | 2.626 (2) | 170 (3) |
O2W—H2W2···O2B | 0.77 (2) | 1.97 (2) | 2.733 (3) | 168 (3) |
O3W—H1W3···O3B | 0.77 (2) | 1.87 (2) | 2.636 (2) | 172 (3) |
O3W—H2W3···O2C | 0.78 (1) | 1.94 (2) | 2.706 (3) | 172 (3) |
N1A—H1AB···O3Wii | 0.94 (3) | 1.82 (3) | 2.754 (3) | 172 (3) |
N1A—H1AA···O2A | 0.90 (3) | 1.89 (3) | 2.776 (3) | 168 (3) |
C1A—H1AC···O2W | 0.99 | 2.57 | 3.362 (3) | 136 |
C2A—H2AB···O3Bii | 0.99 | 2.51 | 3.498 (3) | 175 |
C4A—H4AA···O2Ciii | 0.99 | 2.47 | 3.441 (3) | 166 |
C7A—H7A···I1Biii | 0.95 | 3.32 | 4.212 (2) | 156 |
C11A—H11A···O1Biv | 0.98 | 2.51 | 3.225 (4) | 130 |
N1B—H1BA···O2B | 0.91 (3) | 1.87 (3) | 2.780 (3) | 174 (3) |
N1B—H1BB···O2Wii | 0.92 (3) | 1.85 (3) | 2.768 (3) | 176 (2) |
C1B—H1BC···O3W | 0.99 | 2.44 | 3.229 (3) | 136 |
C2B—H2BB···O3Aii | 0.99 | 2.63 | 3.619 (3) | 174 |
C4B—H4BA···O2Biii | 0.99 | 2.51 | 3.491 (3) | 170 |
C4B—H4BB···O2W | 0.99 | 2.52 | 3.260 (3) | 131 |
C9B—H9B···I1Bii | 0.95 | 3.25 | 4.020 (3) | 139 |
N1C—H1CA···O2C | 0.96 (3) | 1.78 (3) | 2.732 (3) | 172 (3) |
N1C—H1CA···O3C | 0.96 (3) | 2.64 (3) | 3.297 (3) | 126 (2) |
N1C—H1CB···O1Wii | 0.83 (3) | 1.96 (3) | 2.781 (3) | 172 (3) |
C1C—H1CC···O1Wv | 0.99 | 2.39 | 3.299 (3) | 152 |
C4C—H4CA···O2Aiii | 0.99 | 2.45 | 3.438 (3) | 174 |
C9C—H9C···I1Aii | 0.95 | 3.29 | 4.013 (3) | 135 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, −y+1/2, z−1/2. |
C11H17N2O+·C8H7O2−·H2O | Z = 2 |
Mr = 346.42 | F(000) = 372 |
Triclinic, P1 | Dx = 1.305 Mg m−3 |
a = 6.1481 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.3467 (12) Å | Cell parameters from 9904 reflections |
c = 19.980 (4) Å | θ = 2.8–27.5° |
α = 80.190 (6)° | µ = 0.09 mm−1 |
β = 86.089 (5)° | T = 90 K |
γ = 82.843 (6)° | Plate, colourless |
V = 881.3 (3) Å3 | 0.29 × 0.21 × 0.02 mm |
Bruker D8 Venture dual source diffractometer | 4059 independent reflections |
Radiation source: microsource | 3137 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.041 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −7→7 |
Tmin = 0.877, Tmax = 0.959 | k = −9→9 |
23917 measured reflections | l = −25→25 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0124P)2 + 0.3732P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
4059 reflections | Δρmax = 0.19 e Å−3 |
245 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0038 (8) |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
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. |
Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.23887 (18) | 0.74787 (16) | 0.54355 (5) | 0.0192 (2) | |
H1A | 0.203 (3) | 0.727 (2) | 0.4961 (9) | 0.042 (5)* | |
H1B | 0.271 (3) | 0.871 (2) | 0.5385 (8) | 0.033 (4)* | |
N2 | 0.28444 (17) | 0.65390 (15) | 0.68884 (5) | 0.0179 (2) | |
C1 | 0.4273 (2) | 0.61887 (18) | 0.57271 (6) | 0.0202 (3) | |
H1C | 0.558241 | 0.630796 | 0.541287 | 0.024* | |
H1D | 0.392248 | 0.489067 | 0.578218 | 0.024* | |
C2 | 0.4760 (2) | 0.66315 (19) | 0.64091 (6) | 0.0196 (3) | |
H2A | 0.598899 | 0.573865 | 0.660243 | 0.024* | |
H2B | 0.522549 | 0.789461 | 0.634542 | 0.024* | |
C3 | 0.0887 (2) | 0.76711 (19) | 0.66009 (6) | 0.0211 (3) | |
H3A | 0.108509 | 0.900258 | 0.656176 | 0.025* | |
H3B | −0.039758 | 0.743193 | 0.691596 | 0.025* | |
C4 | 0.0427 (2) | 0.7273 (2) | 0.59089 (6) | 0.0220 (3) | |
H4A | 0.002660 | 0.599190 | 0.595399 | 0.026* | |
H4B | −0.082879 | 0.814471 | 0.572187 | 0.026* | |
C5 | 0.3246 (2) | 0.68052 (18) | 0.75566 (6) | 0.0183 (3) | |
C6 | 0.5285 (2) | 0.62481 (19) | 0.78350 (6) | 0.0227 (3) | |
H6 | 0.644111 | 0.569862 | 0.756838 | 0.027* | |
C7 | 0.5680 (2) | 0.6472 (2) | 0.84923 (7) | 0.0254 (3) | |
H7 | 0.709269 | 0.608607 | 0.866686 | 0.030* | |
C8 | 0.4021 (2) | 0.7252 (2) | 0.88893 (6) | 0.0240 (3) | |
C9 | 0.1971 (2) | 0.7774 (2) | 0.86282 (7) | 0.0274 (3) | |
H9 | 0.080563 | 0.827557 | 0.890402 | 0.033* | |
C10 | 0.1588 (2) | 0.7577 (2) | 0.79726 (7) | 0.0252 (3) | |
H10 | 0.017294 | 0.797357 | 0.780137 | 0.030* | |
O1 | 0.42146 (17) | 0.75852 (16) | 0.95411 (5) | 0.0337 (3) | |
C11 | 0.6322 (3) | 0.7136 (3) | 0.98204 (7) | 0.0392 (4) | |
H11A | 0.623438 | 0.740327 | 1.028619 | 0.059* | |
H11B | 0.737047 | 0.788298 | 0.954254 | 0.059* | |
H11C | 0.681120 | 0.581268 | 0.982463 | 0.059* | |
O2 | 0.12234 (15) | 0.71150 (13) | 0.41700 (4) | 0.0241 (2) | |
O3 | 0.39970 (17) | 0.87663 (14) | 0.37969 (5) | 0.0321 (3) | |
C12 | 0.2413 (2) | 0.79566 (18) | 0.36975 (7) | 0.0206 (3) | |
C13 | 0.1882 (2) | 0.79539 (18) | 0.29744 (6) | 0.0190 (3) | |
C14 | 0.3302 (2) | 0.86250 (19) | 0.24411 (7) | 0.0229 (3) | |
H14 | 0.457991 | 0.912589 | 0.253423 | 0.027* | |
C15 | 0.2855 (2) | 0.8564 (2) | 0.17733 (7) | 0.0259 (3) | |
H15 | 0.384517 | 0.901179 | 0.141471 | 0.031* | |
C16 | 0.0986 (2) | 0.78599 (19) | 0.16202 (7) | 0.0241 (3) | |
C17 | −0.0448 (2) | 0.72276 (19) | 0.21558 (7) | 0.0226 (3) | |
H17 | −0.174944 | 0.676288 | 0.206177 | 0.027* | |
C18 | −0.0004 (2) | 0.72670 (18) | 0.28226 (6) | 0.0201 (3) | |
H18 | −0.099671 | 0.682046 | 0.318066 | 0.024* | |
C19 | 0.0474 (3) | 0.7789 (2) | 0.08986 (7) | 0.0353 (4) | |
H19A | −0.003498 | 0.658960 | 0.087676 | 0.053* | |
H19B | 0.179989 | 0.793648 | 0.060251 | 0.053* | |
H19C | −0.067539 | 0.879581 | 0.074736 | 0.053* | |
O1W | 0.72107 (18) | 0.87492 (14) | 0.46115 (5) | 0.0241 (2) | |
H1W | 0.600 (3) | 0.874 (3) | 0.4328 (10) | 0.062 (6)* | |
H2W | 0.850 (3) | 0.813 (3) | 0.4429 (10) | 0.060 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0202 (6) | 0.0197 (6) | 0.0178 (6) | −0.0037 (5) | −0.0013 (4) | −0.0026 (4) |
N2 | 0.0149 (5) | 0.0234 (6) | 0.0157 (5) | −0.0021 (4) | −0.0007 (4) | −0.0038 (4) |
C1 | 0.0192 (7) | 0.0225 (7) | 0.0187 (6) | −0.0006 (5) | −0.0003 (5) | −0.0045 (5) |
C2 | 0.0162 (6) | 0.0244 (7) | 0.0184 (6) | −0.0033 (5) | 0.0006 (5) | −0.0034 (5) |
C3 | 0.0156 (6) | 0.0276 (7) | 0.0199 (7) | −0.0012 (6) | −0.0008 (5) | −0.0037 (5) |
C4 | 0.0175 (7) | 0.0277 (7) | 0.0208 (7) | −0.0037 (6) | −0.0009 (5) | −0.0026 (5) |
C5 | 0.0198 (7) | 0.0187 (7) | 0.0166 (6) | −0.0047 (5) | 0.0001 (5) | −0.0020 (5) |
C6 | 0.0188 (7) | 0.0298 (8) | 0.0197 (7) | −0.0016 (6) | 0.0009 (5) | −0.0059 (5) |
C7 | 0.0191 (7) | 0.0358 (8) | 0.0214 (7) | −0.0026 (6) | −0.0041 (5) | −0.0043 (6) |
C8 | 0.0269 (8) | 0.0303 (8) | 0.0160 (6) | −0.0056 (6) | −0.0009 (5) | −0.0059 (5) |
C9 | 0.0250 (7) | 0.0362 (9) | 0.0210 (7) | 0.0008 (6) | 0.0024 (6) | −0.0092 (6) |
C10 | 0.0197 (7) | 0.0334 (8) | 0.0224 (7) | −0.0002 (6) | −0.0020 (5) | −0.0064 (6) |
O1 | 0.0288 (6) | 0.0545 (7) | 0.0199 (5) | −0.0010 (5) | −0.0044 (4) | −0.0138 (5) |
C11 | 0.0319 (9) | 0.0664 (12) | 0.0227 (8) | −0.0079 (8) | −0.0061 (6) | −0.0135 (7) |
O2 | 0.0261 (5) | 0.0270 (5) | 0.0194 (5) | −0.0023 (4) | −0.0018 (4) | −0.0044 (4) |
O3 | 0.0324 (6) | 0.0365 (6) | 0.0310 (6) | −0.0122 (5) | −0.0115 (5) | −0.0059 (4) |
C12 | 0.0207 (7) | 0.0171 (7) | 0.0243 (7) | 0.0025 (5) | −0.0051 (5) | −0.0061 (5) |
C13 | 0.0187 (6) | 0.0185 (7) | 0.0198 (6) | 0.0008 (5) | −0.0025 (5) | −0.0045 (5) |
C14 | 0.0176 (7) | 0.0236 (7) | 0.0283 (7) | −0.0037 (6) | −0.0015 (5) | −0.0059 (6) |
C15 | 0.0241 (7) | 0.0307 (8) | 0.0218 (7) | −0.0031 (6) | 0.0029 (5) | −0.0032 (6) |
C16 | 0.0266 (7) | 0.0261 (7) | 0.0195 (7) | 0.0009 (6) | −0.0033 (5) | −0.0055 (5) |
C17 | 0.0216 (7) | 0.0234 (7) | 0.0244 (7) | −0.0034 (6) | −0.0048 (5) | −0.0061 (5) |
C18 | 0.0194 (7) | 0.0195 (7) | 0.0210 (7) | −0.0020 (5) | −0.0006 (5) | −0.0027 (5) |
C19 | 0.0397 (9) | 0.045 (1) | 0.0223 (7) | −0.0043 (8) | −0.0038 (7) | −0.0080 (7) |
O1W | 0.0229 (5) | 0.0260 (5) | 0.0245 (5) | −0.0045 (4) | −0.0043 (4) | −0.0045 (4) |
N1—C1 | 1.4864 (17) | C9—H9 | 0.9500 |
N1—C4 | 1.4879 (17) | C10—H10 | 0.9500 |
N1—H1A | 1.028 (17) | O1—C11 | 1.4242 (18) |
N1—H1B | 0.939 (16) | C11—H11A | 0.9800 |
N2—C5 | 1.4239 (16) | C11—H11B | 0.9800 |
N2—C3 | 1.4669 (16) | C11—H11C | 0.9800 |
N2—C2 | 1.4674 (16) | O2—C12 | 1.2759 (16) |
C1—C2 | 1.5111 (17) | O3—C12 | 1.2461 (16) |
C1—H1C | 0.9900 | C12—C13 | 1.5032 (18) |
C1—H1D | 0.9900 | C13—C18 | 1.3917 (18) |
C2—H2A | 0.9900 | C13—C14 | 1.3935 (18) |
C2—H2B | 0.9900 | C14—C15 | 1.3897 (19) |
C3—C4 | 1.5131 (18) | C14—H14 | 0.9500 |
C3—H3A | 0.9900 | C15—C16 | 1.3894 (19) |
C3—H3B | 0.9900 | C15—H15 | 0.9500 |
C4—H4A | 0.9900 | C16—C17 | 1.3937 (19) |
C4—H4B | 0.9900 | C16—C19 | 1.5074 (19) |
C5—C6 | 1.3918 (18) | C17—C18 | 1.3840 (18) |
C5—C10 | 1.3974 (18) | C17—H17 | 0.9500 |
C6—C7 | 1.3920 (18) | C18—H18 | 0.9500 |
C6—H6 | 0.9500 | C19—H19A | 0.9800 |
C7—C8 | 1.3777 (19) | C19—H19B | 0.9800 |
C7—H7 | 0.9500 | C19—H19C | 0.9800 |
C8—O1 | 1.3809 (16) | O1W—H1W | 0.97 (2) |
C8—C9 | 1.381 (2) | O1W—H2W | 0.94 (2) |
C9—C10 | 1.3809 (19) | ||
C1—N1—C4 | 109.09 (10) | C7—C8—C9 | 118.96 (12) |
C1—N1—H1A | 113.3 (9) | O1—C8—C9 | 115.52 (12) |
C4—N1—H1A | 109.7 (9) | C10—C9—C8 | 121.06 (13) |
C1—N1—H1B | 109.9 (10) | C10—C9—H9 | 119.5 |
C4—N1—H1B | 108.5 (10) | C8—C9—H9 | 119.5 |
H1A—N1—H1B | 106.2 (13) | C9—C10—C5 | 121.16 (13) |
C5—N2—C3 | 114.15 (10) | C9—C10—H10 | 119.4 |
C5—N2—C2 | 114.57 (10) | C5—C10—H10 | 119.4 |
C3—N2—C2 | 112.07 (10) | C8—O1—C11 | 117.39 (11) |
N1—C1—C2 | 110.21 (11) | O1—C11—H11A | 109.5 |
N1—C1—H1C | 109.6 | O1—C11—H11B | 109.5 |
C2—C1—H1C | 109.6 | H11A—C11—H11B | 109.5 |
N1—C1—H1D | 109.6 | O1—C11—H11C | 109.5 |
C2—C1—H1D | 109.6 | H11A—C11—H11C | 109.5 |
H1C—C1—H1D | 108.1 | H11B—C11—H11C | 109.5 |
N2—C2—C1 | 111.9 (1) | O3—C12—O2 | 124.23 (12) |
N2—C2—H2A | 109.2 | O3—C12—C13 | 117.92 (12) |
C1—C2—H2A | 109.2 | O2—C12—C13 | 117.85 (11) |
N2—C2—H2B | 109.2 | C18—C13—C14 | 118.71 (12) |
C1—C2—H2B | 109.2 | C18—C13—C12 | 121.19 (11) |
H2A—C2—H2B | 107.9 | C14—C13—C12 | 120.10 (12) |
N2—C3—C4 | 112.90 (11) | C15—C14—C13 | 120.20 (12) |
N2—C3—H3A | 109.0 | C15—C14—H14 | 119.9 |
C4—C3—H3A | 109.0 | C13—C14—H14 | 119.9 |
N2—C3—H3B | 109.0 | C16—C15—C14 | 121.25 (13) |
C4—C3—H3B | 109.0 | C16—C15—H15 | 119.4 |
H3A—C3—H3B | 107.8 | C14—C15—H15 | 119.4 |
N1—C4—C3 | 110.50 (11) | C15—C16—C17 | 118.16 (12) |
N1—C4—H4A | 109.5 | C15—C16—C19 | 121.89 (13) |
C3—C4—H4A | 109.5 | C17—C16—C19 | 119.95 (13) |
N1—C4—H4B | 109.5 | C18—C17—C16 | 120.95 (12) |
C3—C4—H4B | 109.5 | C18—C17—H17 | 119.5 |
H4A—C4—H4B | 108.1 | C16—C17—H17 | 119.5 |
C6—C5—C10 | 116.85 (12) | C17—C18—C13 | 120.71 (12) |
C6—C5—N2 | 121.63 (12) | C17—C18—H18 | 119.6 |
C10—C5—N2 | 121.48 (12) | C13—C18—H18 | 119.6 |
C5—C6—C7 | 122.01 (13) | C16—C19—H19A | 109.5 |
C5—C6—H6 | 119.0 | C16—C19—H19B | 109.5 |
C7—C6—H6 | 119.0 | H19A—C19—H19B | 109.5 |
C8—C7—C6 | 119.92 (13) | C16—C19—H19C | 109.5 |
C8—C7—H7 | 120.0 | H19A—C19—H19C | 109.5 |
C6—C7—H7 | 120.0 | H19B—C19—H19C | 109.5 |
C7—C8—O1 | 125.52 (12) | H1W—O1W—H2W | 109.5 (16) |
C4—N1—C1—C2 | −59.83 (13) | C8—C9—C10—C5 | 1.5 (2) |
C5—N2—C2—C1 | 175.50 (11) | C6—C5—C10—C9 | 0.1 (2) |
C3—N2—C2—C1 | −52.38 (14) | N2—C5—C10—C9 | 177.80 (13) |
N1—C1—C2—N2 | 57.29 (14) | C7—C8—O1—C11 | 2.0 (2) |
C5—N2—C3—C4 | −176.52 (11) | C9—C8—O1—C11 | −177.61 (14) |
C2—N2—C3—C4 | 51.15 (14) | O3—C12—C13—C18 | −172.58 (12) |
C1—N1—C4—C3 | 58.20 (14) | O2—C12—C13—C18 | 8.03 (18) |
N2—C3—C4—N1 | −54.40 (15) | O3—C12—C13—C14 | 8.23 (19) |
C3—N2—C5—C6 | −162.71 (12) | O2—C12—C13—C14 | −171.15 (12) |
C2—N2—C5—C6 | −31.58 (17) | C18—C13—C14—C15 | −1.47 (19) |
C3—N2—C5—C10 | 19.66 (17) | C12—C13—C14—C15 | 177.74 (12) |
C2—N2—C5—C10 | 150.78 (12) | C13—C14—C15—C16 | 0.8 (2) |
C10—C5—C6—C7 | −1.0 (2) | C14—C15—C16—C17 | 0.6 (2) |
N2—C5—C6—C7 | −178.78 (12) | C14—C15—C16—C19 | 179.81 (14) |
C5—C6—C7—C8 | 0.5 (2) | C15—C16—C17—C18 | −1.2 (2) |
C6—C7—C8—O1 | −178.52 (13) | C19—C16—C17—C18 | 179.54 (13) |
C6—C7—C8—C9 | 1.1 (2) | C16—C17—C18—C13 | 0.5 (2) |
C7—C8—C9—C10 | −2.0 (2) | C14—C13—C18—C17 | 0.85 (19) |
O1—C8—C9—C10 | 177.58 (13) | C12—C13—C18—C17 | −178.35 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 1.028 (17) | 1.714 (17) | 2.7391 (15) | 174.1 (15) |
N1—H1B···O1Wi | 0.939 (16) | 1.873 (17) | 2.7977 (16) | 167.8 (14) |
C1—H1C···O1W | 0.99 | 2.46 | 3.2617 (17) | 138 |
C2—H2B···O3i | 0.99 | 2.52 | 3.5088 (17) | 174 |
C4—H4A···O2ii | 0.99 | 2.55 | 3.5294 (17) | 169 |
C4—H4B···O1Wiii | 0.99 | 2.54 | 3.3184 (17) | 135 |
O1W—H1W···O3 | 0.97 (2) | 1.67 (2) | 2.6418 (14) | 176.5 (18) |
O1W—H2W···O2iv | 0.94 (2) | 1.83 (2) | 2.7626 (15) | 170.5 (17) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z. |
Acknowledgements
One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
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