research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methyl­­idene]-6-meth­­oxy-3,4-di­hydro­naphthalen-1(2H)-one and 3-[(E)-(6-meth­­oxy-1-oxo-1,2,3,4-tetra­hydro­naphthalen-2-yl­idene)meth­yl]pyridin-2(1H)-one

CROSSMARK_Color_square_no_text.svg

aArmstrong State University, 11935 Abercorn St. Savanah GA 31419, USA
*Correspondence e-mail: Sarah.Zingles@armstrong.edu

Edited by R. F. Baggio, Comisión Nacional de Energía Atómica, Argentina (Received 18 May 2016; accepted 8 June 2016; online 14 June 2016)

The title compounds C17H14BrNO2, (I), and C17H15NO3, (II), were obtained from the reaction of 6-meth­oxy-3,4-di­hydro-2H-naphthalen-1-one and 2-bromo­nicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the crystal structure of compound (I), there are no short contacts or hydrogen bonds. The structure does display ππ inter­actions between adjacent benzene rings and adjacent pyridyl rings. Compound (II) contains two independent mol­ecules, A and B, in the asymmetric unit; both are non-planar, the dihedral angles between the meth­oxy­benzene and 1H-pyridin-2-one mean planes being 35.07 (9)° in A and 35.28 (9)°in B. In each mol­ecule, the 1H-pyridin-2-one unit participates in inter­molecular N—H⋯O hydrogen bonding to another mol­ecule of the same type (A to A or B to B). The structure also displays ππ inter­actions between the pyridyl and the benzene rings of non-equivalent mol­ecules (viz., A to B and B to A).

1. Chemical context

In order to address the need for new therapeutic agents, medicinal chemists have often looked to nature for inspiration. Our research strategy to synthesize novel compounds considered analogs of the natural product chalcone, which contains two aromatic rings and an α-β-unsaturated ketone. Chalcones, bioactive defense mol­ecules found in plants and used in traditional Chinese medicine, have demonstrated anti­cancer, anti­bacterial, anti­fungal, and anti-inflammatory properties (Nowakowska, 2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]; Katsori et al., 2011[Katsori, A. M. & Hadjipavlou-Litina, D. (2011). Expert Opin. Ther. Pat. 21, 1575-1596.]). Chalcones that contain meth­oxy groups (Shenvi et al., 2013[Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.]; Bandgar et al., 2010[Bandgar, B. P., Gawande, S. S., Bodade, R. G., Totre, J. V. & Khobragade, C. N. (2010). Bioorg. Med. Chem. 18, 1364-1370.]) and/or pyridine groups (Prasad et al., 2008[Prasad, Y. R., Kumar, P. P., Kumar, P. R. & Rao, A. S. (2008). E-J. Chem. 5, 144-148.]; Yee et al., 2005[Yee, S. W., Jarno, L., Gomaa, M. S., Elford, C., Ooi, L. L., Coogan, M. P., McClelland, R., Nicholson, R. I., Evans, B. A. J., Brancale, A. & Simons, C. (2005). J. Med. Chem. 48, 7123-7131.]) have demonstrated activity against a variety of cancer cell lines and anti­biotic-resistant bacteria. Thus, we set out to create a library of chalcones that combine those two functional groups. During the synthesis of the title compound (I)[link] by the Claisen–Schmidt condensation of 6-meth­oxy-3,4-di­hydro-2H-naphthalen-1-one and 2-bromo­nicotinaldehyde, two different types of crystals were obtained – those of the desired chalcone (I)[link] and those of the oxidized product (II)[link]. The title compound (I)[link] is a chalcone analog of one currently being studied for its potential anti­cancer and anti­bacterial activity [unpublished results].

[Scheme 1]

2. Structural commentary

Compound (I)[link] is non-planar (Fig. 1[link]) with the pyridyl and the benzene ring being rotated by 73.61 (11)°. The C1—Br1 bond distance is 1.916 (4) Å. In compound (II)[link], which presents two independent mol­ecules in the asymmetric unit (A and B, Fig. 2[link]), the Br atom is replaced by an oxygen atom, with C—O distances O1A—C1A = 1.258 (3) and O1B—C1B = 1.257 (3) Å. The mol­ecules are also non-planar, the benzene–pyridyl angle being 36.18 (10)° in A and 35.91 (10)° in B.

[Figure 1]
Figure 1
A view of the mol­ecular structure of compound (I)[link], showing the atom and ring labeling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
A view of the mol­ecular structure of compound (II)[link], showing the atom and ring labeling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

In the crystal structure of (I)[link], mol­ecules are linked by Br⋯π and ππ inter­actions. The Br1⋯Cg1i distance is 3.635 (3) Å [symmetry code: (i) −1 + x, y, z; Cg1 is the centroid of the benzene ring] and has a `face-on' geometry. There are two ππ inter­actions in the crystal between adjacent benzene rings, Cg1⋯Cg1ii = 3.944 (4) Å [symmetry code: (ii) 1 − x, 1 − y, 1 − z] and between adjacent pyridyl rings, Cg2⋯Cg2iii = 3.639 (4) Å [symmetry code: (iii) −x, 1 − y, −z]. The ππ inter­actions form ribbons in the ([\overline{1}]01) plane (Fig. 3[link]), which are held together by the Br⋯π inter­actions (Fig. 4[link]).

[Figure 3]
Figure 3
A view of hydrogen-bonded dimers formed in compound (II)[link]. Only mol­ecule A is shown, for simplicity. Hydrogen bonds (see Table1) are drawn with dashed lines.
[Figure 4]
Figure 4
N—H⋯O hydrogen bonding in (II)[link] between 1H-pyridin-2-one unit between mol­ecule of the same type

In each one of the independent mol­ecules in (II)[link], the 1H-pyridin-2-one unit participates in inter­molecular N—H⋯O hydrogen bonding, with a classical R22 (8) synthon, to another mol­ecule of the same type (A to A or B to B), see Fig. 5[link] and Table 1[link] for details. These hydrogen-bonding inter­actions form dimers that are reminiscent of those frequently observed between carb­oxy­lic acids. The hydrogen-bonded units are linked by ππ stacking inter­actions between the benzene and pyridyl rings in adjacent mol­ecules of different type (AB or BA inter­actions) (Fig. 6[link]); Cg3⋯Cg4i = 3.875 (4) and Cg5⋯Cg6ii = 3.857 (4) Å [symmetry codes: (i) 3 − x, 1 − y, −z; (ii) 1 − x, 1 − y, 1 − z; Cg3 and Cg4 are the centroids of the pyridyl and benzene rings of mol­ecule A, Cg5 and Cg6 are the corresponding centroids in mol­ecule B].

Table 1
Hydrogen-bond geometry (Å, °) for (II)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O1Ai 0.96 (3) 1.82 (3) 2.778 (3) 178 (3)
N1B—H1B⋯O1Bii 0.98 (3) 1.80 (3) 2.778 (3) 176 (3)
Symmetry codes: (i) -x+3, -y+1, -z; (ii) -x+1, -y+2, -z+1.
[Figure 5]
Figure 5
Dimers formed by hydrogen-bonding inter­actions in (II)[link].
[Figure 6]
Figure 6
The hydrogen-bonded units in (II)[link] are linked by ππ stacking inter­actions between the phenyl and pyridyl rings in adjacent mol­ecules of different type.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37 with four updates, Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for structures containing the combined tetra­lone and pyridine backbone returned no hits. The search was broadened by changing the nitro­gen to carbon, which returned 43 hits. The carbon–containing version of (I)[link] has been reported (Dimmock et al., 2002[Dimmock, J. R., Zello, G. A., Oloo, E. O., Quail, J. W., Kraatz, H. B., Perjési, P., Aradi, F., Takács-Novák, K., Allen, T. M., Santos, C. L., Balzarini, J., De Clercq, E. & Stables, J. P. (2002). J. Med. Chem. 45, 3103-3111.]; Yee et al., 2005[Yee, S. W., Jarno, L., Gomaa, M. S., Elford, C., Ooi, L. L., Coogan, M. P., McClelland, R., Nicholson, R. I., Evans, B. A. J., Brancale, A. & Simons, C. (2005). J. Med. Chem. 48, 7123-7131.]). Many of these similar chalcones also demonstrated biological activities (Dimmock et al., 2002[Dimmock, J. R., Zello, G. A., Oloo, E. O., Quail, J. W., Kraatz, H. B., Perjési, P., Aradi, F., Takács-Novák, K., Allen, T. M., Santos, C. L., Balzarini, J., De Clercq, E. & Stables, J. P. (2002). J. Med. Chem. 45, 3103-3111.]).

5. Synthesis and crystallization

6-Meth­oxy-3,4-di­hydro-2H-naphthalen-1-one (1 mmol) and 2-bromo­nicotinaldehyde (1 mmol) were dissolved in ethanol (5 mL). An NaOH solution (5 M, 1 mL) was added and the reaction was stirred until a precipitate formed. The reaction mixture was cooled in an ice bath for 20 minutes. The solids were filtered off and recrystallized from MeOH/H2O. Slow evaporation of a methano­lic solution gave dark purple/brown crystals, which proved to be 3-[(E)-(6-meth­oxy-1-oxo-1,2,3,4-tetra­hydro­naphthalen-2-idene)meth­yl]pyridin-2(1H)-one, (II), and lighter purple crystals which proved to be (E)-2-[(2-bromopyridin-3-yl)methyl­idene]-6-meth­oxy-3,4-di­hydro­naph­thalen-1(2H)-one, (I).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All H atoms were positioned geometrically and refined as riding with C—H = 0.95 or 0.98 Å and Uiso(H) = 1.2Ueq(C).

Table 2
Experimental details

  (I) (II)
Crystal data
Chemical formula C17H14BrNO2 C17H15NO3
Mr 344.21 281.31
Crystal system, space group Monoclinic, P21/c Triclinic, P[\overline{1}]
Temperature (K) 173 173
a, b, c (Å) 8.885 (8), 14.253 (13), 11.583 (11) 8.079 (8), 12.296 (12), 14.009 (13)
α, β, γ (°) 90, 92.760 (9), 90 88.85 (3), 76.969 (16), 89.43 (3)
V3) 1465 (3) 1356 (3)
Z 4 4
Radiation type Mo Kα Mo Kα
μ (mm−1) 2.82 0.10
Crystal size (mm) 0.45 × 0.30 × 0.10 0.50 × 0.20 × 0.20
 
Data collection
Diffractometer Rigaku XtaLAB mini Rigaku XtaLAB mini
Absorption correction Multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.]) Multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.587, 0.754 0.808, 0.981
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 15395, 3363, 2583 14459, 6203, 3987
Rint 0.056 0.049
(sin θ/λ)max−1) 0.650 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.088, 0.99 0.058, 0.157, 1.03
No. of reflections 3363 6203
No. of parameters 190 387
H-atom treatment H-atom parameters constrained H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.26, −0.46 0.21, −0.23
Computer programs: CrystalClear-SM Expert (Rigaku, 2011[Rigaku (2011). Rigaku Corporation, Tokyo, Japan.]), SHELXS97, SHELXS86 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and CrystalStructure (Rigaku, 2011[Rigaku (2011). Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Computing details top

For both compounds, data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXS86 (Sheldrick, 2008) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2011); software used to prepare material for publication: CrystalStructure (Rigaku, 2011).

(I) (E)-2-[(2-Bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one top
Crystal data top
C17H14BrNO2F(000) = 696.00
Mr = 344.21Dx = 1.560 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 3472 reflections
a = 8.885 (8) Åθ = 2.3–27.5°
b = 14.253 (13) ŵ = 2.82 mm1
c = 11.583 (11) ÅT = 173 K
β = 92.760 (9)°Prism, dark-purple/brown
V = 1465 (3) Å30.45 × 0.30 × 0.10 mm
Z = 4
Data collection top
Rigaku XtaLAB mini
diffractometer
2583 reflections with F2 > 2.0σ(F2)
Detector resolution: 6.827 pixels mm-1Rint = 0.056
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
h = 1111
Tmin = 0.587, Tmax = 0.754k = 1818
15395 measured reflectionsl = 1515
3363 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0211P)2 + 1.2385P]
where P = (Fo2 + 2Fc2)/3
3363 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.46 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.13688 (4)0.66365 (2)0.18318 (3)0.05196 (12)
O10.4068 (3)0.77510 (13)0.2922 (2)0.0510 (6)
O20.8298 (3)0.48452 (15)0.56282 (19)0.0521 (6)
N10.1337 (3)0.6115 (2)0.0441 (3)0.0519 (7)
C10.0406 (4)0.63829 (19)0.0420 (3)0.0399 (7)
C20.0701 (5)0.5917 (3)0.1437 (3)0.0569 (9)
C30.0819 (4)0.5971 (3)0.1590 (3)0.0511 (8)
C40.1750 (4)0.6256 (2)0.0669 (3)0.0441 (8)
C50.1155 (4)0.64673 (18)0.0395 (3)0.0366 (7)
C60.2119 (4)0.67894 (19)0.1378 (3)0.0382 (7)
C70.3472 (3)0.64406 (18)0.1728 (3)0.0355 (7)
C80.4221 (4)0.55788 (19)0.1273 (3)0.0397 (7)
C90.4650 (4)0.49170 (19)0.2271 (3)0.0431 (7)
C100.5546 (3)0.53914 (19)0.3242 (3)0.0349 (7)
C110.5366 (3)0.63552 (18)0.3440 (3)0.0352 (7)
C120.4297 (3)0.69188 (19)0.2712 (3)0.0380 (7)
C130.6523 (3)0.48629 (19)0.3960 (3)0.0370 (7)
C140.7322 (4)0.5294 (2)0.4867 (3)0.0411 (7)
C150.7157 (4)0.6258 (3)0.5061 (3)0.0477 (8)
C160.6194 (4)0.6772 (2)0.4356 (3)0.0447 (8)
C170.8613 (4)0.3880 (3)0.5410 (3)0.0539 (9)
H20.13400.57280.20770.0683*
H30.12190.58170.23110.0613*
H40.28040.63090.07580.0530*
H60.17500.72970.18140.0459*
H8A0.51350.57610.08710.0476*
H8B0.35250.52560.07100.0476*
H9A0.37200.46510.25760.0517*
H9B0.52480.43910.19750.0517*
H130.66390.42100.38280.0445*
H150.77120.65530.56820.0572*
H160.60880.74250.44930.0536*
H17A0.93600.36500.59930.0646*
H17B0.90110.38160.46400.0646*
H17C0.76840.35130.54500.0646*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04010 (19)0.0613 (3)0.0558 (3)0.01067 (15)0.01591 (15)0.01474 (16)
O10.0488 (14)0.0315 (12)0.0735 (16)0.0008 (9)0.0093 (12)0.0123 (11)
O20.0533 (14)0.0551 (14)0.0471 (13)0.0012 (11)0.0050 (11)0.0050 (11)
N10.0415 (16)0.0614 (18)0.0525 (17)0.0020 (13)0.0003 (14)0.0138 (14)
C10.0361 (16)0.0365 (16)0.0479 (18)0.0030 (12)0.0094 (14)0.0138 (13)
C20.062 (3)0.063 (3)0.045 (2)0.0061 (18)0.0079 (17)0.0126 (17)
C30.061 (3)0.051 (2)0.0415 (18)0.0011 (16)0.0087 (16)0.0097 (15)
C40.0470 (19)0.0387 (17)0.0478 (19)0.0008 (14)0.0126 (15)0.0097 (14)
C50.0355 (16)0.0307 (15)0.0443 (17)0.0021 (11)0.0084 (13)0.0097 (12)
C60.0387 (17)0.0308 (15)0.0462 (17)0.0009 (12)0.0131 (14)0.0029 (12)
C70.0348 (16)0.0294 (14)0.0434 (17)0.0018 (11)0.0130 (13)0.0027 (12)
C80.0348 (16)0.0411 (17)0.0436 (17)0.0037 (12)0.0052 (13)0.0104 (13)
C90.0448 (18)0.0315 (15)0.0525 (19)0.0045 (13)0.0029 (15)0.0117 (14)
C100.0304 (15)0.0348 (15)0.0406 (16)0.0043 (11)0.0111 (12)0.0073 (12)
C110.0301 (15)0.0323 (14)0.0439 (17)0.0047 (11)0.0103 (13)0.0085 (12)
C120.0347 (16)0.0307 (15)0.0499 (18)0.0049 (12)0.0162 (13)0.0085 (13)
C130.0341 (16)0.0346 (15)0.0432 (16)0.0048 (12)0.0103 (13)0.0059 (13)
C140.0366 (16)0.0471 (18)0.0404 (17)0.0030 (13)0.0098 (13)0.0049 (14)
C150.0425 (19)0.0508 (19)0.0498 (19)0.0093 (15)0.0016 (15)0.0161 (15)
C160.0418 (18)0.0391 (17)0.0543 (19)0.0063 (13)0.0124 (15)0.0162 (14)
C170.054 (3)0.058 (3)0.049 (2)0.0080 (17)0.0013 (16)0.0003 (16)
Geometric parameters (Å, º) top
Br1—C11.916 (4)C11—C161.395 (5)
O1—C121.230 (4)C13—C141.383 (5)
O2—C141.366 (4)C14—C151.400 (5)
O2—C171.428 (4)C15—C161.367 (5)
N1—C11.322 (4)C2—H20.950
N1—C21.339 (5)C3—H30.950
C1—C51.394 (5)C4—H40.950
C2—C31.373 (6)C6—H60.950
C3—C41.379 (5)C8—H8A0.990
C4—C51.396 (5)C8—H8B0.990
C5—C61.466 (4)C9—H9A0.990
C6—C71.345 (4)C9—H9B0.990
C7—C81.504 (4)C13—H130.950
C7—C121.490 (4)C15—H150.950
C8—C91.526 (5)C16—H160.950
C9—C101.507 (4)C17—H17A0.980
C10—C111.403 (4)C17—H17B0.980
C10—C131.394 (4)C17—H17C0.980
C11—C121.477 (4)
Br1···C63.175 (5)C7···H17Cvii3.4744
O1···C62.788 (4)C8···H2ix3.3343
O1···C162.824 (4)C8···H8Axii3.2064
O2···C163.597 (5)C8···H8Bxii3.3383
N1···C42.776 (5)C9···H2ix3.0789
C1···C32.682 (5)C9···H4xii3.4093
C2···C52.739 (5)C10···H3xii3.5613
C4···C73.115 (5)C11···H17Cvii3.0608
C4···C83.215 (5)C12···H4ii3.3921
C5···C83.129 (5)C12···H9Biii3.5629
C7···C102.898 (5)C12···H17Cvii2.8936
C8···C112.883 (5)C13···H3xii2.9961
C9···C122.918 (5)C14···H9Avii3.1465
C10···C152.779 (5)C14···H17Aiv3.4966
C11···C142.786 (5)C14···H17Biv3.5174
C13···C162.777 (5)C15···H2xi3.5940
C13···C172.816 (5)C15···H9Avii3.1588
Br1···C11i3.545 (4)C15···H17Aiv3.3838
O1···C3ii3.482 (5)C15···H17Biv3.4081
O1···C4ii3.039 (5)C16···H17Cvii3.4878
O1···C9iii3.302 (5)C17···H6vi3.4285
O2···O2iv3.447 (5)H2···O2xiii2.9448
O2···C17iv3.549 (5)H2···C8ix3.3343
C3···O1v3.482 (5)H2···C9ix3.0789
C4···O1v3.039 (5)H2···C15xiii3.5940
C5···C17iii3.572 (6)H2···H8Bix2.9228
C9···O1vi3.302 (5)H2···H9Aix2.2314
C10···C14vii3.576 (5)H2···H9Bix3.4838
C11···Br1viii3.545 (4)H2···H15xiii2.9364
C14···C10vii3.576 (5)H3···Br1ix3.5417
C17···O2iv3.549 (5)H3···O1v3.2529
C17···C5vi3.572 (6)H3···C10xii3.5613
Br1···H62.9275H3···C13xii2.9961
O1···H62.4600H3···H6v2.9190
O1···H162.5365H3···H9Bxii3.1583
O2···H132.6545H3···H13xii2.6509
O2···H152.4904H3···H17Bxii2.7453
N1···H33.2414H4···O1v2.3578
C1···H23.1134H4···C9xii3.4093
C1···H43.2223H4···C12v3.3921
C1···H62.7708H4···H6v3.5320
C2···H43.2239H4···H8Axii3.4784
C4···H23.2145H4···H9Bxii2.4924
C4···H63.2363H4···H16v3.4309
C4···H8A3.4942H4···H17Ciii3.1940
C4···H8B2.6124H6···C3ii3.2152
C5···H33.2719H6···C4ii3.5709
C5···H8B2.7337H6···C17iii3.4285
C6···H42.6663H6···H3ii2.9190
C6···H8A3.1347H6···H4ii3.5320
C6···H8B2.6513H6···H13iii3.1833
C7···H42.9181H6···H17Avii3.0803
C7···H9A2.7383H6···H17Biii2.8049
C7···H9B3.3265H6···H17Ciii3.2031
C8···H42.8141H6···H17Cvii3.3881
C8···H63.3683H8A···Br1viii3.4801
C9···H132.6622H8A···N1viii3.5846
C10···H8A2.8022H8A···C8xii3.2064
C10···H8B3.3699H8A···H4xii3.4784
C10···H163.2663H8A···H8Axii2.9651
C11···H8A3.0904H8A···H8Bxii2.6613
C11···H9A2.9829H8A···H9Bxii3.3050
C11···H9B3.2731H8A···H16v3.1746
C11···H133.2840H8B···N1ix2.7636
C11···H153.2626H8B···C2ix3.1634
C12···H62.5034H8B···C8xii3.3383
C12···H8A2.8241H8B···H2ix2.9228
C12···H8B3.3631H8B···H8Axii2.6613
C12···H9A3.2750H8B···H8Bxii3.2432
C12···H162.6445H8B···H9Bxii3.3817
C13···H9A2.9123H9A···O1vi3.4120
C13···H9B2.6028H9A···O2vii2.9006
C13···H153.2694H9A···N1ix3.3590
C13···H17B2.7501H9A···C2ix3.0408
C13···H17C2.7511H9A···C14vii3.1465
C14···H163.2512H9A···C15vii3.1588
C14···H17A3.2009H9A···H2ix2.2314
C14···H17B2.6071H9A···H15vii2.9801
C14···H17C2.6424H9B···O1vi2.4164
C15···H133.2725H9B···C3xii3.5819
C17···H132.5192H9B···C4xii3.2624
H2···H32.3066H9B···C12vi3.5629
H3···H42.3381H9B···H2ix3.4838
H4···H63.4655H9B···H3xii3.1583
H4···H8A2.8438H9B···H4xii2.4924
H4···H8B2.3341H9B···H8Axii3.3050
H6···H8B3.5753H9B···H8Bxii3.3817
H8A···H9A2.8675H9B···H16vi3.4571
H8A···H9B2.3336H13···O1vi2.9497
H8B···H9A2.3265H13···C3xii3.5284
H8B···H9B2.4075H13···H3xii2.6509
H9A···H132.9774H13···H6vi3.1833
H9B···H132.4383H15···Br1xiv2.9998
H13···H17A3.4907H15···C1xiv3.4050
H13···H17B2.3340H15···H2xi2.9364
H13···H17C2.2821H15···H9Avii2.9801
H15···H162.3091H15···H17Aiv3.3316
Br1···H3ix3.5417H15···H17Biv3.0003
Br1···H8Ai3.4801H16···N1xiv3.0906
Br1···H15x2.9998H16···H4ii3.4309
Br1···H17Avii3.0445H16···H8Aii3.1746
O1···H3ii3.2529H16···H9Biii3.4571
O1···H4ii2.3578H17A···Br1vii3.0445
O1···H9Aiii3.4120H17A···O2iv3.5822
O1···H9Biii2.4164H17A···C4vi3.5660
O1···H13iii2.9497H17A···C5vi3.5209
O1···H17Cvii3.0841H17A···C6vii3.4317
O2···H2xi2.9448H17A···C14iv3.4966
O2···H9Avii2.9006H17A···C15iv3.3838
O2···H17Aiv3.5822H17A···H6vii3.0803
O2···H17Biv3.0868H17A···H15iv3.3316
N1···H8Ai3.5846H17B···O2iv3.0868
N1···H8Bix2.7636H17B···C3xii3.5563
N1···H9Aix3.3590H17B···C5vi3.3507
N1···H16x3.0906H17B···C6vi3.2597
C1···H15x3.4050H17B···C14iv3.5174
C2···H8Bix3.1634H17B···C15iv3.4081
C2···H9Aix3.0408H17B···H3xii2.7453
C3···H6v3.2152H17B···H6vi2.8049
C3···H9Bxii3.5819H17B···H15iv3.0003
C3···H13xii3.5284H17C···O1vii3.0841
C3···H17Bxii3.5563H17C···C4vi3.2643
C4···H6v3.5709H17C···C5vi3.2590
C4···H9Bxii3.2624H17C···C6vi3.2537
C4···H17Aiii3.5660H17C···C7vii3.4744
C4···H17Ciii3.2643H17C···C11vii3.0608
C5···H17Aiii3.5209H17C···C12vii2.8936
C5···H17Biii3.3507H17C···C16vii3.4878
C5···H17Ciii3.2590H17C···H4vi3.1940
C6···H17Avii3.4317H17C···H6vi3.2031
C6···H17Biii3.2597H17C···H6vii3.3881
C6···H17Ciii3.2537
C14—O2—C17117.4 (3)C11—C16—C15121.2 (3)
C1—N1—C2115.9 (3)N1—C2—H2118.055
Br1—C1—N1114.2 (3)C3—C2—H2118.055
Br1—C1—C5119.2 (3)C2—C3—H3120.838
N1—C1—C5126.6 (3)C4—C3—H3120.843
N1—C2—C3123.9 (4)C3—C4—H4119.759
C2—C3—C4118.3 (4)C5—C4—H4119.753
C3—C4—C5120.5 (3)C5—C6—H6116.619
C1—C5—C4114.8 (3)C7—C6—H6116.628
C1—C5—C6123.7 (3)C7—C8—H8A109.712
C4—C5—C6121.4 (3)C7—C8—H8B109.712
C5—C6—C7126.8 (3)C9—C8—H8A109.713
C6—C7—C8126.9 (3)C9—C8—H8B109.719
C6—C7—C12117.4 (3)H8A—C8—H8B108.195
C8—C7—C12115.6 (3)C8—C9—H9A108.968
C7—C8—C9109.8 (3)C8—C9—H9B108.968
C8—C9—C10113.1 (3)C10—C9—H9A108.972
C9—C10—C11120.1 (3)C10—C9—H9B108.971
C9—C10—C13119.6 (3)H9A—C9—H9B107.765
C11—C10—C13120.3 (3)C10—C13—H13120.158
C10—C11—C12121.0 (3)C14—C13—H13120.170
C10—C11—C16118.7 (3)C14—C15—H15120.081
C12—C11—C16120.3 (3)C16—C15—H15120.079
O1—C12—C7120.8 (3)C11—C16—H16119.393
O1—C12—C11121.3 (3)C15—C16—H16119.404
C7—C12—C11117.8 (3)O2—C17—H17A109.466
C10—C13—C14119.7 (3)O2—C17—H17B109.477
O2—C14—C13124.7 (3)O2—C17—H17C109.473
O2—C14—C15115.1 (3)H17A—C17—H17B109.467
C13—C14—C15120.3 (3)H17A—C17—H17C109.469
C14—C15—C16119.8 (3)H17B—C17—H17C109.476
C17—O2—C14—C135.8 (4)C12—C7—C8—C950.7 (3)
C17—O2—C14—C15174.6 (3)C7—C8—C9—C1052.0 (3)
C1—N1—C2—C30.6 (5)C8—C9—C10—C1127.9 (4)
C2—N1—C1—Br1179.0 (3)C8—C9—C10—C13153.9 (3)
C2—N1—C1—C50.8 (5)C9—C10—C11—C120.4 (4)
Br1—C1—C5—C4179.22 (15)C9—C10—C11—C16179.0 (3)
Br1—C1—C5—C63.3 (4)C9—C10—C13—C14178.6 (3)
N1—C1—C5—C41.1 (4)C11—C10—C13—C140.4 (4)
N1—C1—C5—C6178.6 (3)C13—C10—C11—C12177.9 (3)
N1—C2—C3—C40.7 (5)C13—C10—C11—C160.8 (4)
C2—C3—C4—C51.1 (5)C10—C11—C12—O1175.7 (3)
C3—C4—C5—C11.2 (4)C10—C11—C12—C72.8 (4)
C3—C4—C5—C6178.7 (3)C10—C11—C16—C150.6 (5)
C1—C5—C6—C7139.3 (3)C12—C11—C16—C15178.1 (3)
C4—C5—C6—C743.4 (4)C16—C11—C12—O12.9 (5)
C5—C6—C7—C87.3 (5)C16—C11—C12—C7178.5 (3)
C5—C6—C7—C12176.3 (3)C10—C13—C14—O2179.4 (3)
C6—C7—C8—C9125.8 (3)C10—C13—C14—C150.2 (5)
C6—C7—C12—O125.6 (4)O2—C14—C15—C16179.3 (3)
C6—C7—C12—C11152.9 (3)C13—C14—C15—C160.4 (5)
C8—C7—C12—O1157.5 (3)C14—C15—C16—C110.0 (5)
C8—C7—C12—C1123.9 (4)
Symmetry codes: (i) x1, y, z; (ii) x, y+3/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+2, y+1, z+1; (v) x, y+3/2, z1/2; (vi) x+1, y1/2, z+1/2; (vii) x+1, y+1, z+1; (viii) x+1, y, z; (ix) x, y+1, z; (x) x1, y+3/2, z1/2; (xi) x+1, y, z+1; (xii) x+1, y+1, z; (xiii) x1, y, z1; (xiv) x+1, y+3/2, z+1/2.
(II) 3-[(E)-(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one top
Crystal data top
C17H15NO3Z = 4
Mr = 281.31F(000) = 592.00
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 8.079 (8) ÅCell parameters from 3099 reflections
b = 12.296 (12) Åθ = 1.7–27.5°
c = 14.009 (13) ŵ = 0.10 mm1
α = 88.85 (3)°T = 173 K
β = 76.969 (16)°Prism, purple
γ = 89.43 (3)°0.50 × 0.20 × 0.20 mm
V = 1356 (3) Å3
Data collection top
Rigaku XtaLAB mini
diffractometer
3987 reflections with F2 > 2.0σ(F2)
Detector resolution: 6.827 pixels mm-1Rint = 0.049
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
h = 1010
Tmin = 0.808, Tmax = 0.981k = 1515
14459 measured reflectionsl = 1818
6203 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2529P]
where P = (Fo2 + 2Fc2)/3
6203 reflections(Δ/σ)max < 0.001
387 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A1.35958 (19)0.48754 (12)0.11653 (11)0.0326 (4)
O1B0.63793 (19)0.98881 (12)0.38219 (11)0.0332 (4)
O2A0.9197 (3)0.46536 (12)0.39203 (12)0.0402 (4)
O2B1.0769 (2)0.96666 (12)0.10487 (11)0.0387 (4)
O3A0.6064 (3)0.15815 (13)0.75027 (11)0.0442 (5)
O3B1.3821 (2)0.65941 (13)0.24660 (11)0.0412 (5)
N1A1.4242 (3)0.36168 (15)0.00284 (13)0.0298 (4)
N1B0.5793 (3)0.86238 (15)0.50526 (13)0.0316 (5)
C1A1.3324 (3)0.39499 (17)0.08683 (15)0.0280 (5)
C1B0.6684 (3)0.89632 (17)0.41435 (15)0.0278 (5)
C2A1.4049 (3)0.26451 (18)0.04361 (17)0.0354 (6)
C2B0.6040 (3)0.76448 (18)0.54789 (16)0.0350 (6)
C3A1.2856 (3)0.19377 (18)0.00387 (16)0.0347 (6)
C3B0.7238 (3)0.69400 (18)0.50207 (16)0.0342 (6)
C4A1.1847 (3)0.22236 (17)0.09530 (16)0.0307 (5)
C4B0.8213 (3)0.72330 (18)0.40892 (16)0.0321 (5)
C5A1.2066 (3)0.31888 (17)0.13941 (15)0.0272 (5)
C5B0.7950 (3)0.81991 (17)0.36243 (15)0.0280 (5)
C6A1.1081 (3)0.35595 (17)0.23403 (15)0.0274 (5)
C6B0.8909 (3)0.85753 (17)0.26640 (15)0.0270 (5)
C7A1.0120 (3)0.29973 (17)0.30996 (15)0.0277 (5)
C7B0.9845 (3)0.80123 (17)0.19149 (15)0.0266 (5)
C8A0.9851 (3)0.17786 (17)0.31644 (15)0.0326 (5)
C8B1.0132 (3)0.67944 (17)0.18803 (16)0.0333 (5)
C9A0.9762 (3)0.13030 (17)0.41899 (15)0.0287 (5)
C9B1.0185 (3)0.63272 (17)0.08736 (15)0.0283 (5)
C10A0.8586 (3)0.19351 (17)0.49738 (15)0.0261 (5)
C10B1.1337 (3)0.69533 (16)0.00597 (15)0.0252 (5)
C11A0.8353 (3)0.30523 (17)0.48528 (15)0.0288 (5)
C11B1.1553 (3)0.80721 (17)0.01437 (15)0.0280 (5)
C12A0.9227 (3)0.36508 (17)0.39546 (15)0.0281 (5)
C12B1.0721 (3)0.86650 (17)0.10352 (15)0.0279 (5)
C13A0.7811 (3)0.14120 (17)0.58544 (15)0.0285 (5)
C13B1.2104 (3)0.64271 (17)0.08067 (15)0.0278 (5)
C14A0.6831 (3)0.20038 (18)0.66097 (16)0.0334 (5)
C14B1.3057 (3)0.70229 (18)0.15880 (16)0.0316 (5)
C15A0.6584 (4)0.3122 (2)0.64862 (18)0.0454 (7)
C15B1.3265 (4)0.8140 (2)0.15060 (17)0.0421 (7)
C16A0.7334 (4)0.36361 (19)0.56189 (17)0.0417 (6)
C16B1.2532 (3)0.86551 (19)0.06559 (16)0.0374 (6)
C17A0.6263 (4)0.04374 (19)0.76739 (17)0.0396 (6)
C17B1.3661 (4)0.54477 (19)0.25898 (17)0.0399 (6)
H1A1.501 (4)0.414 (3)0.041 (2)0.054 (8)*
H1B0.499 (4)0.914 (3)0.543 (2)0.058 (9)*
H2A1.47500.24630.10530.0424*
H2B0.53600.74570.61060.0419*
H3A1.27040.12590.02420.0417*
H3B0.74170.62630.53210.0410*
H4A1.09860.17380.12780.0368*
H4B0.90800.67520.37700.0385*
H6A1.11240.43210.24360.0329*
H6B0.88650.93380.25500.0324*
H8A11.07930.14230.26970.0391*
H8A20.87810.16120.29660.0391*
H8B10.92090.64370.23680.0400*
H8B21.12170.66240.20680.0400*
H9A10.93680.05410.42160.0344*
H9A21.09150.12970.43220.0344*
H9B11.05790.55620.08660.0340*
H9B20.90220.63320.07560.0340*
H13A0.79580.06510.59350.0341*
H13B1.19730.56650.08600.0333*
H15A0.58980.35240.70020.0545*
H15B1.39180.85450.20420.0505*
H16A0.71600.43940.55380.0501*
H16B1.26870.94150.06060.0449*
H17A0.74750.02520.75390.0475*
H17B0.57100.00260.72420.0475*
H17C0.57380.02540.83590.0475*
H17D1.24550.52590.24720.0479*
H17E1.41860.50470.21220.0479*
H17F1.42300.52540.32590.0479*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0333 (9)0.0271 (8)0.0320 (8)0.0061 (7)0.0041 (7)0.0016 (7)
O1B0.0326 (9)0.0290 (9)0.0324 (9)0.0070 (7)0.0039 (7)0.0002 (7)
O2A0.0543 (11)0.0227 (8)0.0368 (9)0.0025 (7)0.0041 (8)0.0012 (7)
O2B0.0513 (11)0.0219 (8)0.0369 (9)0.0033 (7)0.0032 (8)0.0018 (7)
O3A0.0536 (11)0.0373 (10)0.0307 (9)0.0040 (8)0.0132 (8)0.0055 (8)
O3B0.0462 (11)0.0365 (10)0.0317 (9)0.0032 (8)0.0113 (8)0.0075 (7)
N1A0.0258 (10)0.0283 (10)0.0302 (10)0.0019 (8)0.0045 (8)0.0008 (8)
N1B0.0299 (11)0.0310 (10)0.0289 (10)0.0008 (8)0.0041 (8)0.0011 (8)
C1A0.0240 (11)0.0277 (11)0.0298 (11)0.0010 (9)0.0006 (9)0.0012 (9)
C1B0.0265 (11)0.0276 (11)0.0268 (11)0.0036 (9)0.0009 (9)0.0001 (9)
C2A0.0347 (13)0.0337 (13)0.0334 (12)0.0006 (10)0.0018 (10)0.0062 (10)
C2B0.0348 (13)0.0345 (13)0.0300 (12)0.0063 (10)0.0042 (10)0.0039 (10)
C3A0.0417 (14)0.0251 (12)0.0331 (12)0.0036 (10)0.0007 (10)0.0022 (10)
C3B0.0383 (13)0.0278 (12)0.0328 (12)0.0007 (10)0.0004 (10)0.0027 (10)
C4A0.0304 (12)0.0276 (12)0.0314 (12)0.0044 (9)0.0015 (9)0.0035 (9)
C4B0.0321 (12)0.0276 (12)0.0334 (12)0.0009 (9)0.0001 (10)0.0067 (10)
C5A0.0263 (11)0.0263 (11)0.0267 (11)0.0002 (9)0.0014 (9)0.0031 (9)
C5B0.0261 (11)0.0270 (11)0.0283 (11)0.0001 (9)0.0005 (9)0.0047 (9)
C6A0.0295 (12)0.0222 (11)0.0285 (11)0.0012 (9)0.0027 (9)0.0006 (9)
C6B0.0277 (11)0.0224 (10)0.0283 (11)0.0004 (8)0.0008 (9)0.0002 (9)
C7A0.0261 (11)0.0255 (11)0.0286 (11)0.0026 (9)0.0003 (9)0.0003 (9)
C7B0.0260 (11)0.0243 (11)0.0272 (11)0.0015 (8)0.0009 (9)0.0006 (9)
C8A0.0371 (13)0.0258 (12)0.0283 (12)0.0003 (9)0.0067 (10)0.0010 (9)
C8B0.0406 (13)0.0247 (11)0.0289 (12)0.0018 (10)0.0044 (10)0.0016 (9)
C9A0.0301 (12)0.0221 (11)0.0300 (11)0.0006 (9)0.0015 (9)0.0003 (9)
C9B0.0304 (12)0.0218 (11)0.0300 (11)0.0024 (9)0.0010 (9)0.0005 (9)
C10A0.0235 (11)0.0248 (11)0.0276 (11)0.0009 (8)0.0006 (9)0.0010 (9)
C10B0.0214 (10)0.0242 (11)0.0274 (11)0.0009 (8)0.0004 (9)0.0001 (9)
C11A0.0311 (12)0.0233 (11)0.0285 (11)0.0039 (9)0.0000 (9)0.0009 (9)
C11B0.0287 (12)0.0230 (11)0.0292 (11)0.0044 (9)0.0002 (9)0.0028 (9)
C12A0.0279 (11)0.0244 (11)0.0293 (11)0.0023 (9)0.0010 (9)0.0017 (9)
C12B0.0281 (11)0.0236 (11)0.0300 (11)0.0019 (9)0.0022 (9)0.0024 (9)
C13A0.0283 (11)0.0224 (11)0.0316 (11)0.0012 (9)0.0004 (9)0.0008 (9)
C13B0.0274 (11)0.0245 (11)0.0290 (11)0.0022 (9)0.0010 (9)0.0027 (9)
C14A0.0365 (13)0.0299 (12)0.0279 (11)0.0020 (10)0.0048 (10)0.0029 (10)
C14B0.0289 (12)0.0334 (12)0.0273 (11)0.0015 (9)0.0051 (9)0.0054 (10)
C15A0.0554 (17)0.0346 (14)0.0347 (13)0.0151 (12)0.0137 (12)0.0008 (11)
C15B0.0507 (16)0.0337 (13)0.0319 (13)0.0136 (11)0.0122 (11)0.0006 (10)
C16A0.0537 (16)0.0247 (12)0.0368 (13)0.0109 (11)0.0099 (12)0.0027 (10)
C16B0.0450 (15)0.0276 (12)0.0333 (12)0.0084 (10)0.0054 (11)0.0029 (10)
C17A0.0469 (15)0.0341 (13)0.0335 (13)0.0079 (11)0.0006 (11)0.0078 (10)
C17B0.0470 (15)0.0342 (13)0.0355 (13)0.0066 (11)0.0023 (11)0.0078 (11)
Geometric parameters (Å, º) top
O1A—C1A1.258 (3)C11B—C12B1.480 (3)
O1B—C1B1.257 (3)C11B—C16B1.405 (3)
O2A—C12A1.233 (3)C13A—C14A1.385 (3)
O2B—C12B1.233 (3)C13B—C14B1.388 (3)
O3A—C14A1.360 (3)C14A—C15A1.400 (4)
O3A—C17A1.436 (4)C14B—C15B1.395 (4)
O3B—C14B1.360 (3)C15A—C16A1.374 (4)
O3B—C17B1.434 (4)C15B—C16B1.369 (4)
N1A—C1A1.375 (3)N1A—H1A0.96 (3)
N1A—C2A1.360 (4)N1B—H1B0.98 (3)
N1B—C1B1.373 (3)C2A—H2A0.950
N1B—C2B1.366 (4)C2B—H2B0.950
C1A—C5A1.451 (3)C3A—H3A0.950
C1B—C5B1.459 (3)C3B—H3B0.950
C2A—C3A1.354 (4)C4A—H4A0.950
C2B—C3B1.351 (4)C4B—H4B0.950
C3A—C4A1.404 (3)C6A—H6A0.950
C3B—C4B1.406 (4)C6B—H6B0.950
C4A—C5A1.380 (4)C8A—H8A10.990
C4B—C5B1.381 (4)C8A—H8A20.990
C5A—C6A1.463 (3)C8B—H8B10.990
C5B—C6B1.462 (3)C8B—H8B20.990
C6A—C7A1.349 (3)C9A—H9A10.990
C6B—C7B1.347 (3)C9A—H9A20.990
C7A—C8A1.514 (4)C9B—H9B10.990
C7A—C12A1.496 (3)C9B—H9B20.990
C7B—C8B1.513 (4)C13A—H13A0.950
C7B—C12B1.497 (3)C13B—H13B0.950
C8A—C9A1.527 (4)C15A—H15A0.950
C8B—C9B1.525 (4)C15B—H15B0.950
C9A—C10A1.504 (3)C16A—H16A0.950
C9B—C10B1.503 (3)C16B—H16B0.950
C10A—C11A1.397 (4)C17A—H17A0.980
C10A—C13A1.398 (3)C17A—H17B0.980
C10B—C11B1.399 (4)C17A—H17C0.980
C10B—C13B1.400 (3)C17B—H17D0.980
C11A—C12A1.482 (3)C17B—H17E0.980
C11A—C16A1.402 (4)C17B—H17F0.980
O1A···C2A3.542 (4)C11A···H3Bvii3.4817
O1A···C6A2.812 (4)C11A···H4Bvii3.1490
O1B···C2B3.542 (4)C11B···H2Ai3.5524
O1B···C6B2.821 (4)C11B···H3Av3.5010
O2A···C6A2.754 (4)C11B···H4Av3.1694
O2A···C16A2.792 (4)C12A···H3Bvii3.1055
O2B···C6B2.750 (4)C12A···H17Dv3.0137
O2B···C16B2.798 (4)C12A···H17Fv3.4151
O3B···C16B3.599 (4)C12B···H3Av3.2054
N1A···C4A2.710 (4)C12B···H17Avii3.0581
N1B···C4B2.721 (4)C12B···H17Cvii3.4482
C1A···C3A2.819 (4)C13A···H1Biii3.28 (4)
C1B···C3B2.829 (4)C13A···H4Bvii3.5271
C2A···C5A2.790 (4)C13A···H9A1xi3.2812
C2B···C5B2.782 (4)C13A···H9A2xi3.4733
C4A···C7A3.177 (4)C13B···H1Ai3.25 (3)
C4A···C8A3.193 (4)C13B···H4Av3.5120
C4B···C7B3.167 (4)C13B···H9B1v3.2984
C4B···C8B3.187 (5)C13B···H9B2v3.5161
C5A···C8A3.201 (4)C14A···H2Aviii3.3823
C5B···C8B3.198 (4)C14A···H4Bvii3.5794
C7A···C10A2.926 (4)C14A···H8B2vii3.2033
C7B···C10B2.932 (4)C14B···H2Bix3.3802
C8A···C11A2.887 (4)C14B···H4Av3.5312
C8B···C11B2.886 (4)C14B···H8A2v3.1403
C9A···C12A2.938 (5)C15A···H2Aviii3.5133
C9B···C12B2.932 (5)C15A···H4Bvii3.4446
C10A···C15A2.786 (4)C15A···H8B2vii3.0027
C10B···C15B2.782 (4)C15A···H17Eviii3.3979
C11A···C14A2.788 (4)C15A···H17Fviii3.2020
C11B···C14B2.791 (4)C15B···H2Bix3.5065
C13A···C16A2.781 (5)C15B···H4Av3.3787
C13A···C17A2.823 (4)C15B···H8A2v2.9149
C13B···C16B2.783 (5)C15B···H17Bxii3.2749
C13B···C17B2.819 (4)C15B···H17Cxii3.2706
O1A···O1Ai3.540 (4)C16A···H3B3.2475
O1A···O3Bi3.528 (4)C16A···H4Bvii3.2293
O1A···N1Ai2.778 (3)C16A···H17Fviii3.3113
O1A···C9B3.366 (4)C16B···H3Aiv3.2754
O1A···C17Bi3.316 (5)C16B···H4Av3.1988
O1B···O1Bii3.556 (4)C16B···H17Cxii3.2954
O1B···O3Aiii3.530 (4)C17A···H2Aviii3.1643
O1B···N1Bii2.778 (3)C17A···H8A1xi3.2466
O1B···C9Aiv3.395 (4)C17A···H15Bxiii2.9788
O1B···C17Aiii3.343 (5)C17A···H16Bxiii3.5415
O2A···C3B3.431 (4)C17B···H2Bix3.1756
O2A···C4B3.262 (5)C17B···H8B1v3.2548
O2A···C17Bv3.282 (5)C17B···H15Aix2.9481
O2B···O2Bvi3.519 (4)H1A···O1Ai1.82 (3)
O2B···C3Aiv3.391 (4)H1A···N1Ai2.93 (3)
O2B···C4Aiv3.263 (5)H1A···C1Ai2.71 (3)
O2B···C16Bvi3.490 (5)H1A···C10Bi3.36 (3)
O2B···C17Avii3.300 (5)H1A···C13Bi3.25 (3)
O3A···O1Biii3.530 (4)H1A···H1Ai2.42 (4)
O3A···C2Aviii3.269 (4)H1A···H8B2i3.5253
O3B···O1Ai3.528 (4)H1A···H9B1i3.5001
O3B···C2Bix3.277 (4)H1A···H9B2v3.4543
O3B···C7Av3.522 (5)H1A···H13B3.2363
O3B···C12Av3.586 (4)H1A···H13Bi3.3392
N1A···O1Ai2.778 (3)H1A···H17E2.8349
N1A···C13Bi3.411 (5)H1B···O1Bii1.80 (3)
N1A···C14Bi3.554 (5)H1B···N1Bii2.92 (3)
N1B···O1Bii2.778 (3)H1B···C1Bii2.70 (3)
N1B···C13Aiii3.430 (5)H1B···C10Aiii3.36 (3)
N1B···C14Aiii3.584 (5)H1B···C13Aiii3.28 (4)
C1A···C14Bi3.494 (5)H1B···H1Bii2.42 (4)
C1B···C14Aiii3.473 (5)H1B···H8A2iii3.4722
C2A···O3Aix3.269 (4)H1B···H9A1iii3.4644
C2B···O3Bviii3.277 (4)H1B···H9A2vii3.4365
C3A···O2Bx3.391 (4)H1B···H13Aiv3.2562
C3B···O2A3.431 (4)H1B···H13Aiii3.3828
C3B···C12Avii3.537 (5)H1B···H15Bviii3.5086
C4A···O2Bx3.263 (5)H1B···H17Biv2.9558
C4A···C10Bv3.345 (5)H2A···O1Ai3.5344
C4A···C11Bv3.461 (5)H2A···O3Aix2.3436
C4B···O2A3.262 (5)H2A···C11Bi3.5524
C4B···C10Avii3.331 (5)H2A···C14Aix3.3823
C4B···C11Avii3.440 (5)H2A···C15Aix3.5133
C7A···O3Bv3.522 (5)H2A···C17Aix3.1643
C9A···O1Bx3.395 (4)H2A···H8B2i3.4372
C9B···O1A3.366 (4)H2A···H9B2v3.3194
C10A···C4Bvii3.331 (5)H2A···H15Aix2.9548
C10B···C4Av3.345 (5)H2A···H17Cix2.9064
C11A···C4Bvii3.440 (5)H2A···H17E3.5542
C11B···C4Av3.461 (5)H2B···O1Bii3.5356
C12A···O3Bv3.586 (4)H2B···O3Bviii2.3441
C12A···C3Bvii3.537 (5)H2B···C14Bviii3.3802
C12A···C17Bv3.493 (5)H2B···C15Bviii3.5065
C12B···C17Avii3.543 (5)H2B···C17Bviii3.1756
C13A···N1Biii3.430 (5)H2B···H8A2iii3.4956
C13B···N1Ai3.411 (5)H2B···H9A2vii3.3172
C14A···N1Biii3.584 (5)H2B···H15Bviii2.9363
C14A···C1Biii3.473 (5)H2B···H17Fviii2.9233
C14B···N1Ai3.554 (5)H3A···O2Bx2.8622
C14B···C1Ai3.494 (5)H3A···O2Bv3.4629
C16B···O2Bvi3.490 (5)H3A···C7Bv3.5482
C17A···O1Biii3.343 (5)H3A···C11Bv3.5010
C17A···O2Bvii3.300 (5)H3A···C12Bv3.2054
C17A···C12Bvii3.543 (5)H3A···C16Bx3.2754
C17B···O1Ai3.316 (5)H3A···H9B2v3.3943
C17B···O2Av3.282 (5)H3A···H16Bx2.3352
C17B···C12Av3.493 (5)H3A···H17Cix3.0415
O1A···H1A2.43 (3)H3B···O2A2.9423
O1A···H6A2.4489H3B···O2Avii3.3296
O1B···H1B2.45 (3)H3B···C7Avii3.4330
O1B···H6B2.4642H3B···C11Avii3.4817
O2A···H6A2.3405H3B···C12Avii3.1055
O2A···H16A2.4985H3B···C16A3.2475
O2B···H6B2.3395H3B···H9A2vii3.3936
O2B···H16B2.5041H3B···H16A2.3163
O3A···H13A2.6507H3B···H17Fviii3.1267
O3A···H15A2.4872H4A···O2Bx2.5858
O3B···H13B2.6483H4A···C10Bv3.3216
O3B···H15B2.4886H4A···C11Bv3.1694
N1A···H3A3.2111H4A···C13Bv3.5120
N1B···H3B3.2243H4A···C14Bv3.5312
C1A···H2A3.2667H4A···C15Bv3.3787
C1A···H4A3.2935H4A···C16Bv3.1988
C1A···H6A2.5404H4A···H17Axi3.3142
C1B···H2B3.2618H4B···O2A2.5865
C1B···H4B3.3034H4B···C10Avii3.3067
C1B···H6B2.5497H4B···C11Avii3.1490
C2A···H4A3.2254H4B···C13Avii3.5271
C2B···H4B3.2206H4B···C14Avii3.5794
C3A···H1A3.21 (3)H4B···C15Avii3.4446
C3B···H1B3.23 (3)H4B···C16Avii3.2293
C4A···H2A3.2394H4B···H17Dv3.4945
C4A···H6A3.3079H6A···C8B3.2615
C4A···H8A12.5782H6A···C9B3.4562
C4A···H8A23.3840H6A···H8B13.0246
C4B···H2B3.2327H6A···H8B22.8674
C4B···H6B3.3041H6A···H9B12.7650
C4B···H8B12.5740H6A···H17Dv2.9212
C4B···H8B23.3796H6B···C8Aiv3.2921
C5A···H1A3.26 (3)H6B···C9Aiv3.5559
C5A···H3A3.2879H6B···H8A1iv3.0467
C5A···H8A12.8540H6B···H8A2iv2.8645
C5A···H8A23.5979H6B···H9A1iv2.8936
C5B···H1B3.29 (3)H6B···H15Bvi3.5873
C5B···H3B3.2916H6B···H16Bvi3.5601
C5B···H8B12.8515H6B···H17Avii2.9790
C5B···H8B23.5983H8A1···O2Bx3.1964
C6A···H4A2.7250H8A1···C17Axi3.2466
C6A···H8A12.6674H8A1···H6Bx3.0467
C6A···H8A23.0367H8A1···H13Axi3.4374
C6B···H4B2.7201H8A1···H17Axi2.4631
C6B···H8B12.6704H8A1···H17Bxi3.3408
C6B···H8B23.0366H8A1···H17Cxi3.5252
C7A···H4A2.9547H8A2···O1Bx2.9375
C7A···H9A13.3699H8A2···O3Bv3.2070
C7A···H9A22.8359H8A2···C14Bv3.1403
C7B···H4B2.9446H8A2···C15Bv2.9149
C7B···H9B13.3674H8A2···H1Biii3.4722
C7B···H9B22.8279H8A2···H2Biii3.4956
C8A···H4A2.5955H8A2···H6Bx2.8645
C8A···H6A3.3662H8A2···H15Bv2.7849
C8B···H4B2.5908H8B1···O2A3.0557
C8B···H6B3.3663H8B1···C17Bv3.2548
C9A···H13A2.6607H8B1···H6A3.0246
C9B···H13B2.6681H8B1···H17Dv2.4760
C10A···H8A13.3531H8B1···H17Ev3.3942
C10A···H8A22.8177H8B1···H17Fv3.4716
C10A···H16A3.2727H8B2···O1A2.9740
C10B···H8B13.3536H8B2···O3Avii3.2863
C10B···H8B22.8138H8B2···C14Avii3.2033
C10B···H16B3.2734H8B2···C15Avii3.0027
C11A···H8A23.1634H8B2···H1Ai3.5253
C11A···H9A13.2766H8B2···H2Ai3.4372
C11A···H9A22.9629H8B2···H6A2.8674
C11A···H13A3.2772H8B2···H15Avii2.9180
C11A···H15A3.2692H9A1···O1Bx2.7271
C11B···H8B23.1615H9A1···C1Bx2.9439
C11B···H9B13.2767H9A1···C5Bx3.2986
C11B···H9B22.9529H9A1···C6Bx3.3610
C11B···H13B3.2834H9A1···C9Axi3.3310
C11B···H15B3.2680H9A1···C13Axi3.2812
C12A···H6A2.4573H9A1···H1Biii3.4644
C12A···H8A13.3660H9A1···H6Bx2.8936
C12A···H8A22.9520H9A1···H9A1xi2.9166
C12A···H9A23.2682H9A1···H9A2xi2.9945
C12A···H16A2.6312H9A1···H13Axi2.5694
C12B···H6B2.4593H9A1···H17Axi3.2732
C12B···H8B13.3639H9A2···N1Bvii2.9853
C12B···H8B22.9405H9A2···C1Bvii3.2133
C12B···H9B23.2609H9A2···C2Bvii2.8657
C12B···H16B2.6379H9A2···C3Bvii2.9221
C13A···H9A12.6018H9A2···C4Bvii3.1002
C13A···H9A22.9143H9A2···C5Bvii3.2826
C13A···H15A3.2690H9A2···C13Axi3.4733
C13A···H17A2.6943H9A2···H1Bvii3.4365
C13A···H17B2.8283H9A2···H2Bvii3.3172
C13B···H9B12.6015H9A2···H3Bvii3.3936
C13B···H9B22.9233H9A2···H9A1xi2.9945
C13B···H15B3.2673H9A2···H13Axi2.5567
C13B···H17D2.7230H9A2···H17Axi3.2760
C13B···H17E2.7890H9A2···H17Bxi3.4983
C14A···H16A3.2596H9B1···O1A2.6898
C14A···H17A2.6029H9B1···C1A2.9602
C14A···H17B2.6673H9B1···C5A3.2785
C14A···H17C3.2037H9B1···C6A3.2624
C14B···H16B3.2545H9B1···C9Bv3.5565
C14B···H17D2.6222H9B1···C13Bv3.2984
C14B···H17E2.6492H9B1···H1Ai3.5001
C14B···H17F3.2050H9B1···H6A2.7650
C15A···H13A3.2711H9B1···H9B1v3.1392
C15B···H13B3.2702H9B1···H9B2v3.2489
C17A···H13A2.5215H9B1···H13Bv2.5684
C17B···H13B2.5167H9B1···H17Dv3.0913
H1A···H2A2.2992H9B2···N1Av3.0336
H1B···H2B2.2974H9B2···C1Av3.2985
H2A···H3A2.3127H9B2···C2Av2.8904
H2B···H3B2.3064H9B2···C3Av2.9447
H3A···H4A2.3474H9B2···C4Av3.1532
H3B···H4B2.3525H9B2···C5Av3.3625
H4A···H8A11.9890H9B2···C13Bv3.5161
H4A···H8A22.6223H9B2···H1Av3.4543
H4B···H8B11.9888H9B2···H2Av3.3194
H4B···H8B22.6163H9B2···H3Av3.3943
H6A···H8A13.5813H9B2···H9B1v3.2489
H6B···H8B13.5854H9B2···H13Bv2.5824
H8A1···H9A12.4195H9B2···H17Dv3.0969
H8A1···H9A22.3025H9B2···H17Ev3.3127
H8A2···H9A12.3013H13A···O1Biii3.5115
H8A2···H9A22.8577H13A···N1Bx3.4617
H8B1···H9B12.4135H13A···C9Axi2.9967
H8B1···H9B22.3030H13A···H1Bx3.2562
H8B2···H9B12.3020H13A···H1Biii3.3828
H8B2···H9B22.8566H13A···H8A1xi3.4374
H9A1···H13A2.4265H13A···H9A1xi2.5694
H9A2···H13A2.9957H13A···H9A2xi2.5567
H9B1···H13B2.4275H13B···O1A3.5000
H9B2···H13B3.0136H13B···O1Ai3.5656
H13A···H17A2.2374H13B···N1A3.4371
H13A···H17B2.3898H13B···C1A3.5271
H13A···H17C3.4914H13B···C9Bv3.0242
H13B···H17D2.2690H13B···H1A3.2363
H13B···H17E2.3465H13B···H1Ai3.3392
H13B···H17F3.4883H13B···H9B1v2.5684
H15A···H16A2.3198H13B···H9B2v2.5824
H15B···H16B2.3119H15A···O1Avii3.3651
O1A···H1Ai1.82 (3)H15A···C17Bviii2.9481
O1A···H2Ai3.5344H15A···H2Aviii2.9548
O1A···H8B22.9740H15A···H8B2vii2.9180
O1A···H9B12.6898H15A···H17Dviii3.4425
O1A···H13B3.5000H15A···H17Eviii2.4894
O1A···H13Bi3.5656H15A···H17Fviii2.5707
O1A···H15Avii3.3651H15B···O1Bvi3.1705
O1A···H17Ei2.4719H15B···C17Axii2.9788
O1B···H1Bii1.80 (3)H15B···H1Bix3.5086
O1B···H2Bii3.5356H15B···H2Bix2.9363
O1B···H8A2iv2.9375H15B···H6Bvi3.5873
O1B···H9A1iv2.7271H15B···H8A2v2.7849
O1B···H13Aiii3.5115H15B···H17Axii3.5094
O1B···H15Bvi3.1705H15B···H17Bxii2.3967
O1B···H17Biii2.4912H15B···H17Cxii2.7158
O2A···H3B2.9423H16A···O2Avii3.4235
O2A···H3Bvii3.3296H16A···C3B3.1966
O2A···H4B2.5865H16A···H3B2.3163
O2A···H8B13.0557H16A···H17Fviii2.7900
O2A···H16Avii3.4235H16B···O2Bvi3.1853
O2A···H17Dv2.6679H16B···C3Aiv3.2609
O2A···H17Fv3.1116H16B···C17Axii3.5415
O2B···H3Aiv2.8622H16B···H3Aiv2.3352
O2B···H3Av3.4629H16B···H6Bvi3.5601
O2B···H4Aiv2.5858H16B···H17Bxii3.4993
O2B···H8A1iv3.1964H16B···H17Cxii2.7607
O2B···H16Bvi3.1853H17A···O2Bvii2.6864
O2B···H17Avii2.6864H17A···C6Bvii3.2234
O2B···H17Cvii3.1185H17A···C7Bvii3.2767
O3A···H2Aviii2.3436H17A···C8Axi3.3019
O3A···H8B2vii3.2863H17A···C9Axi3.4878
O3B···H2Bix2.3441H17A···C12Bvii3.0581
O3B···H8A2v3.2070H17A···H4Axi3.3142
N1A···H1Ai2.93 (3)H17A···H6Bvii2.9790
N1A···H9B2v3.0336H17A···H8A1xi2.4631
N1A···H13B3.4371H17A···H9A1xi3.2732
N1A···H17E3.3986H17A···H9A2xi3.2760
N1B···H1Bii2.92 (3)H17A···H15Bxiii3.5094
N1B···H9A2vii2.9853H17B···O1Biii2.4912
N1B···H13Aiv3.4617H17B···N1Bx3.5354
N1B···H17Biv3.5354H17B···C1Biii3.2559
C1A···H1Ai2.71 (3)H17B···C15Bxiii3.2749
C1A···H9B12.9602H17B···H1Bx2.9558
C1A···H9B2v3.2985H17B···H8A1xi3.3408
C1A···H13B3.5271H17B···H9A2xi3.4983
C1A···H17Ei3.2226H17B···H15Bxiii2.3967
C1B···H1Bii2.70 (3)H17B···H16Bxiii3.4993
C1B···H9A1iv2.9439H17C···O2Bvii3.1185
C1B···H9A2vii3.2133H17C···C2Aviii3.5271
C1B···H17Biii3.2559H17C···C3Aviii3.5886
C2A···H9B2v2.8904H17C···C12Bvii3.4482
C2A···H17Cix3.5271H17C···C15Bxiii3.2706
C2B···H9A2vii2.8657H17C···C16Bxiii3.2954
C2B···H17Fviii3.5513H17C···H2Aviii2.9064
C3A···H9B2v2.9447H17C···H3Aviii3.0415
C3A···H16Bx3.2609H17C···H8A1xi3.5252
C3A···H17Cix3.5886H17C···H15Bxiii2.7158
C3B···H9A2vii2.9221H17C···H16Bxiii2.7607
C3B···H16A3.1966H17D···O2Av2.6679
C4A···H9B2v3.1532H17D···C6Av3.1614
C4B···H9A2vii3.1002H17D···C7Av3.2187
C5A···H9B13.2785H17D···C8Bv3.2661
C5A···H9B2v3.3625H17D···C9Bv3.3347
C5B···H9A1iv3.2986H17D···C12Av3.0137
C5B···H9A2vii3.2826H17D···H4Bv3.4945
C6A···H9B13.2624H17D···H6Av2.9212
C6A···H17Dv3.1614H17D···H8B1v2.4760
C6B···H9A1iv3.3610H17D···H9B1v3.0913
C6B···H17Avii3.2234H17D···H9B2v3.0969
C7A···H3Bvii3.4330H17D···H15Aix3.4425
C7A···H17Dv3.2187H17E···O1Ai2.4719
C7B···H3Av3.5482H17E···N1A3.3986
C7B···H17Avii3.2767H17E···C1Ai3.2226
C8A···H6Bx3.2921H17E···C15Aix3.3979
C8A···H17Axi3.3019H17E···H1A2.8349
C8B···H6A3.2615H17E···H2A3.5542
C8B···H17Dv3.2661H17E···H8B1v3.3942
C9A···H6Bx3.5559H17E···H9B2v3.3127
C9A···H9A1xi3.3310H17E···H15Aix2.4894
C9A···H13Axi2.9967H17F···O2Av3.1116
C9A···H17Axi3.4878H17F···C2Bix3.5513
C9B···H6A3.4562H17F···C12Av3.4151
C9B···H9B1v3.5565H17F···C15Aix3.2020
C9B···H13Bv3.0242H17F···C16Aix3.3113
C9B···H17Dv3.3347H17F···H2Bix2.9233
C10A···H1Biii3.36 (3)H17F···H3Bix3.1267
C10A···H4Bvii3.3067H17F···H8B1v3.4716
C10B···H1Ai3.36 (3)H17F···H15Aix2.5707
C10B···H4Av3.3216H17F···H16Aix2.7900
C14A—O3A—C17A117.87 (17)C1A—N1A—H1A116.4 (16)
C14B—O3B—C17B118.04 (17)C2A—N1A—H1A118.6 (16)
C1A—N1A—C2A124.77 (18)C1B—N1B—H1B117.6 (16)
C1B—N1B—C2B124.09 (19)C2B—N1B—H1B118.2 (16)
O1A—C1A—N1A119.19 (18)N1A—C2A—H2A120.047
O1A—C1A—C5A124.94 (19)C3A—C2A—H2A120.062
N1A—C1A—C5A115.9 (2)N1B—C2B—H2B119.577
O1B—C1B—N1B119.22 (18)C3B—C2B—H2B119.570
O1B—C1B—C5B124.91 (19)C2A—C3A—H3A120.562
N1B—C1B—C5B115.87 (19)C4A—C3A—H3A120.571
N1A—C2A—C3A119.9 (2)C2B—C3B—H3B120.798
N1B—C2B—C3B120.9 (2)C4B—C3B—H3B120.786
C2A—C3A—C4A118.9 (3)C3A—C4A—H4A118.985
C2B—C3B—C4B118.4 (3)C5A—C4A—H4A118.981
C3A—C4A—C5A122.0 (2)C3B—C4B—H4B118.977
C3B—C4B—C5B122.0 (2)C5B—C4B—H4B118.991
C1A—C5A—C4A118.51 (19)C5A—C6A—H6A114.725
C1A—C5A—C6A115.3 (2)C7A—C6A—H6A114.724
C4A—C5A—C6A126.10 (19)C5B—C6B—H6B114.869
C1B—C5B—C4B118.65 (19)C7B—C6B—H6B114.869
C1B—C5B—C6B115.41 (19)C7A—C8A—H8A1108.953
C4B—C5B—C6B125.82 (19)C7A—C8A—H8A2108.949
C5A—C6A—C7A130.6 (2)C9A—C8A—H8A1108.951
C5B—C6B—C7B130.3 (2)C9A—C8A—H8A2108.949
C6A—C7A—C8A126.42 (19)H8A1—C8A—H8A2107.768
C6A—C7A—C12A116.3 (2)C7B—C8B—H8B1108.959
C8A—C7A—C12A117.25 (17)C7B—C8B—H8B2108.961
C6B—C7B—C8B126.74 (19)C9B—C8B—H8B1108.958
C6B—C7B—C12B116.4 (2)C9B—C8B—H8B2108.957
C8B—C7B—C12B116.84 (18)H8B1—C8B—H8B2107.760
C7A—C8A—C9A113.13 (19)C8A—C9A—H9A1109.091
C7B—C8B—C9B113.11 (19)C8A—C9A—H9A2109.092
C8A—C9A—C10A112.54 (19)C10A—C9A—H9A1109.085
C8B—C9B—C10B112.72 (19)C10A—C9A—H9A2109.087
C9A—C10A—C11A120.40 (18)H9A1—C9A—H9A2107.832
C9A—C10A—C13A119.5 (2)C8B—C9B—H9B1109.041
C11A—C10A—C13A119.94 (19)C8B—C9B—H9B2109.049
C9B—C10B—C11B120.00 (18)C10B—C9B—H9B1109.055
C9B—C10B—C13B119.72 (19)C10B—C9B—H9B2109.048
C11B—C10B—C13B120.15 (18)H9B1—C9B—H9B2107.811
C10A—C11A—C12A121.74 (18)C10A—C13A—H13A120.007
C10A—C11A—C16A119.34 (19)C14A—C13A—H13A120.000
C12A—C11A—C16A118.8 (2)C10B—C13B—H13B120.131
C10B—C11B—C12B121.83 (18)C14B—C13B—H13B120.134
C10B—C11B—C16B118.97 (19)C14A—C15A—H15A120.013
C12B—C11B—C16B119.2 (2)C16A—C15A—H15A120.010
O2A—C12A—C7A121.79 (19)C14B—C15B—H15B119.841
O2A—C12A—C11A120.46 (19)C16B—C15B—H15B119.843
C7A—C12A—C11A117.75 (19)C11A—C16A—H16A119.693
O2B—C12B—C7B121.47 (19)C15A—C16A—H16A119.690
O2B—C12B—C11B120.49 (18)C11B—C16B—H16B119.642
C7B—C12B—C11B118.04 (19)C15B—C16B—H16B119.641
C10A—C13A—C14A120.0 (2)O3A—C17A—H17A109.475
C10B—C13B—C14B119.7 (2)O3A—C17A—H17B109.477
O3A—C14A—C13A124.7 (2)O3A—C17A—H17C109.471
O3A—C14A—C15A115.17 (19)H17A—C17A—H17B109.471
C13A—C14A—C15A120.1 (2)H17A—C17A—H17C109.464
O3B—C14B—C13B124.3 (2)H17B—C17A—H17C109.469
O3B—C14B—C15B115.61 (19)O3B—C17B—H17D109.470
C13B—C14B—C15B120.1 (2)O3B—C17B—H17E109.468
C14A—C15A—C16A120.0 (3)O3B—C17B—H17F109.473
C14B—C15B—C16B120.3 (2)H17D—C17B—H17E109.466
C11A—C16A—C15A120.6 (3)H17D—C17B—H17F109.473
C11B—C16B—C15B120.7 (3)H17E—C17B—H17F109.478
C17A—O3A—C14A—C13A0.9 (4)C8B—C7B—C12B—O2B169.3 (2)
C17A—O3A—C14A—C15A179.70 (19)C8B—C7B—C12B—C11B10.0 (3)
C17B—O3B—C14B—C13B1.2 (4)C12B—C7B—C8B—C9B38.7 (3)
C17B—O3B—C14B—C15B179.56 (19)C7A—C8A—C9A—C10A48.0 (3)
C1A—N1A—C2A—C3A1.6 (4)C7B—C8B—C9B—C10B48.6 (3)
C2A—N1A—C1A—O1A178.9 (2)C8A—C9A—C10A—C11A30.5 (3)
C2A—N1A—C1A—C5A0.2 (4)C8A—C9A—C10A—C13A153.73 (18)
C1B—N1B—C2B—C3B1.2 (4)C8B—C9B—C10B—C11B31.3 (3)
C2B—N1B—C1B—O1B178.9 (2)C8B—C9B—C10B—C13B152.79 (18)
C2B—N1B—C1B—C5B0.6 (4)C9A—C10A—C11A—C12A0.7 (4)
O1A—C1A—C5A—C4A176.6 (2)C9A—C10A—C11A—C16A176.02 (19)
O1A—C1A—C5A—C6A0.5 (4)C9A—C10A—C13A—C14A175.01 (18)
N1A—C1A—C5A—C4A2.1 (3)C11A—C10A—C13A—C14A0.8 (4)
N1A—C1A—C5A—C6A179.12 (17)C13A—C10A—C11A—C12A176.46 (19)
O1B—C1B—C5B—C4B176.5 (2)C13A—C10A—C11A—C16A0.3 (4)
O1B—C1B—C5B—C6B0.4 (4)C9B—C10B—C11B—C12B2.2 (4)
N1B—C1B—C5B—C4B2.9 (3)C9B—C10B—C11B—C16B175.18 (18)
N1B—C1B—C5B—C6B179.10 (18)C9B—C10B—C13B—C14B174.82 (18)
N1A—C2A—C3A—C4A0.5 (4)C11B—C10B—C13B—C14B1.0 (4)
N1B—C2B—C3B—C4B0.7 (4)C13B—C10B—C11B—C12B178.08 (19)
C2A—C3A—C4A—C5A1.9 (4)C13B—C10B—C11B—C16B0.7 (4)
C2B—C3B—C4B—C5B1.8 (4)C10A—C11A—C12A—O2A169.6 (2)
C3A—C4A—C5A—C1A3.2 (4)C10A—C11A—C12A—C7A11.0 (4)
C3A—C4A—C5A—C6A179.8 (2)C10A—C11A—C16A—C15A0.7 (4)
C3B—C4B—C5B—C1B3.6 (4)C12A—C11A—C16A—C15A176.1 (2)
C3B—C4B—C5B—C6B179.3 (2)C16A—C11A—C12A—O2A7.2 (4)
C1A—C5A—C6A—C7A163.1 (2)C16A—C11A—C12A—C7A172.2 (2)
C4A—C5A—C6A—C7A20.2 (4)C10B—C11B—C12B—O2B171.6 (2)
C1B—C5B—C6B—C7B162.5 (2)C10B—C11B—C12B—C7B9.2 (3)
C4B—C5B—C6B—C7B21.6 (4)C10B—C11B—C16B—C15B0.0 (4)
C5A—C6A—C7A—C8A1.5 (4)C12B—C11B—C16B—C15B177.4 (2)
C5A—C6A—C7A—C12A177.9 (2)C16B—C11B—C12B—O2B5.8 (4)
C5B—C6B—C7B—C8B0.6 (4)C16B—C11B—C12B—C7B173.4 (2)
C5B—C6B—C7B—C12B178.0 (2)C10A—C13A—C14A—O3A178.1 (2)
C6A—C7A—C8A—C9A142.6 (3)C10A—C13A—C14A—C15A1.3 (4)
C6A—C7A—C12A—O2A8.7 (4)C10B—C13B—C14B—O3B178.5 (2)
C6A—C7A—C12A—C11A171.92 (19)C10B—C13B—C14B—C15B0.7 (4)
C8A—C7A—C12A—O2A170.8 (2)O3A—C14A—C15A—C16A178.6 (2)
C8A—C7A—C12A—C11A8.6 (3)C13A—C14A—C15A—C16A0.9 (4)
C12A—C7A—C8A—C9A37.9 (3)O3B—C14B—C15B—C16B179.3 (2)
C6B—C7B—C8B—C9B142.7 (3)C13B—C14B—C15B—C16B0.0 (4)
C6B—C7B—C12B—O2B9.5 (4)C14A—C15A—C16A—C11A0.2 (4)
C6B—C7B—C12B—C11B171.26 (19)C14B—C15B—C16B—C11B0.4 (4)
Symmetry codes: (i) x+3, y+1, z; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x, y+1, z; (v) x+2, y+1, z; (vi) x+2, y+2, z; (vii) x+2, y+1, z+1; (viii) x1, y, z+1; (ix) x+1, y, z1; (x) x, y1, z; (xi) x+2, y, z+1; (xii) x+1, y+1, z1; (xiii) x1, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Ai0.96 (3)1.82 (3)2.778 (3)178 (3)
N1B—H1B···O1Bii0.98 (3)1.80 (3)2.778 (3)176 (3)
Symmetry codes: (i) x+3, y+1, z; (ii) x+1, y+2, z+1.
 

Acknowledgements

MEM and ADG are grateful for the financial support of an ASU Undergraduate Research Grant and SKZ for an ASU Research and Scholarship Grant.

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