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COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 4| April 2016| Pages 583-589
https://doi.org/10.1107/S2056989016004692

Crystal structures of ten enanti­opure Schiff bases bearing a naphthyl group

CROSSMARK_Color_square_no_text.svg
Guadalupe Hernández-Téllez,a* Gloria E. Moreno,a Sylvain Bernès,b Angel Mendoza,c Oscar Portillo,a Pankaj Sharmad and René Gutiérreza

aLaboratorio de Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, A.P. 1067, 72001 Puebla, Pue., Mexico, bInstituto de Física, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico, cCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico, and dInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Delegación Coyoacán, 04510 México D.F., Mexico
*Correspondence e-mail: guadalupe.hernandez@correo.buap.mx

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 March 2016; accepted 17 March 2016; online 31 March 2016)

Using a general solvent-free procedure for the synthesis of chiral Schiff bases, the following compounds were synthesized and their crystal structures determined: (S)-(+)-2-{[(1-phenyl­eth­yl)imino]­meth­yl}naphthalene, C19H17N, (1), (S)-(+)-2-({[(4-methyl­phen­yl)eth­yl]imino}­meth­yl)naphthalene, C20H19N, (2), (R)-(−)-2-({[(4-meth­oxy­lphen­yl)eth­yl]imino}­meth­yl)naphthalene, C20H19NO, (3), (R)-(−)-2-({[(4-fluoro­phen­yl)eth­yl]imino}­meth­yl)naphthalene, C19H16FN, (4), (S)-(+)-2-({[(4-chloro­phen­yl)eth­yl]imino}­meth­yl)naphthalene, C19H16ClN, (5), (S)-(+)-2-({[(4-bromo­phen­yl)eth­yl]imino}­meth­yl)naphthalene, C19H16BrN, (6), (S)-(+)-2-({[1-(naphthalen-1-yl)eth­yl]imino}­meth­yl)naph­thalene, C23H19N, (7), (S)-(+)-2-{[(1-cyclo­hexyl­eth­yl)imino]­meth­yl}naph­tha­lene, C19H23N, (8), (S)-(−)-2-{[(1,2,3,4-tetra­hydro­naphthalen-1-yl)imino]meth­yl}naphthalene, C21H19N, (9), and (+)-2-({[(1S,2S,3S,5R)-2,6,6-tri­methylbi­cyclo­[3.1.1]hept-3-yl]imino}­meth­yl}naphthalene, C21H25N, (10). The moiety provided by the amine generates conformational flexibility for these imines. In the crystals, no strong inter­molecular contacts are observed, in spite of the presence of aromatic groups.

CCDC references: 1425668; 1425667; 1425666; 1425665; 1425664; 1425663; 1425662; 1425661; 1425660; 1425659

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1. Chemical context

Compounds containing an imine group are known to play an important role in living organisms, and some reports have established the presence of imine or azomethine subunits in various natural, natural-derived, and non-natural compounds to be critical to their biological activities (Bringmann et al., 2004[Bringmann, G., Dreyer, M., Faber, J. H., Dalsgaard, P. W., Staerk, D., Jaroszewski, J. W., Ndangalasi, H., Mbago, F., Brun, R. & Christensen, S. B. (2004). J. Nat. Prod. 67, 743-748.]; de Souza et al., 2007[Souza, A. O. de, Galetti, F. C. S., Silva, C. L., Bicalho, B., Parma, M. M., Fonseca, S. F., Marsaioli, A. J., Trindade, A. C. L. B., Gil, R. P. F., Bezerra, F. S., Andrade-Neto, M. & de Oliveira, M. C. F. (2007). Quim. Nova, 30, 1563-1566.]; Guo et al., 2007[Guo, Z., Xing, R., Liu, S., Zhong, Z., Ji, X., Wang, L. & Li, P. C. (2007). Carbohydr. Res. 342, 1329-1332.]). Outside of their biological applications, many Schiff bases also reversibly bind with oxygen, coordinate with and show fluorescent variability with metals, exhibiting photochromism and/or thermochromism, and have been used as catalysts, pigments and dyes, corrosion inhibitors, polymer stabilizers, or precursors in the formation of nanoparticles (Gupta & Sutar, 2008[Gupta, K. C. & Sutar, A. K. (2008). Coord. Chem. Rev. 252, 1420-1450.]; Gupta et al., 2009[Gupta, K. C., Kumar Sutar, A. & Lin, C.-C. (2009). Coord. Chem. Rev. 253, 1926-1946.]; Mishra et al., 2012[Mishra, A. P., Tiwari, A. & Jain, R. K. (2012). Adv. Mat. Lett. 3, 213-219.]). As a result of their widespread utility and applications, the search for better and more convenient synthetic routes to Schiff bases improving reaction temperature, time and yields is a never ending trend.

We are currently engaged in a program dedicated to the synthesis of small Schiff bases using a single-step solvent-free approach. Such procedures may overcome, for example, the hydrolytic susceptibility of the formed imine, since water is eliminated as a gas if the Schiff condensation is exothermic. A recent work in this direction was published, which reports the preparation of 15 Schiff bases formed between 3-eth­oxy­salicyl­aldehyde and primary aromatic amines (Tigineh et al., 2015[Tigineh, G. T., Wen, Y.-S. & Liu, L.-K. (2015). Tetrahedron, 71, 170-175.]). In that case, solid reactants were ground in a mortar, first separately and then together. This mechanochemical conversion is efficient (yields > 99%) and can be modified, if necessary, using a liquid-assisted grinding method (Cinčić et al., 2012[Cinčić, D., Brekalo, I. & Kaitner, B. (2012). Chem. Commun. 48, 11683-11685.]) or a solvent-assisted mechanochemical route (Bowmaker, 2013[Bowmaker, G. A. (2013). Chem. Commun. 49, 334-348.]). Both concepts can even be merged if at least one reactant is a liquid. We used this kind of synthesis for the here reported compounds, using 2-naphthaldehyde (solid, m.p. 331–333 K) and a series of ten chiral liquid primary amines with densities in the range 0.866 to 1.390 g ml−1. All of compounds (1)–(10) were crystallized and their crystal structures confirmed that enanti­opure imines were obtained.

[Scheme 1]

These non-centrosymmetric mol­ecules bearing π-conjugated systems are potentially of inter­est for those who are involved in the synthesis of materials presenting non-linear optical properties. In preliminary tests, a doubling-frequency effect and luminescence have been observed with an Nd:YAG infrared laser (1064 nm) and an UV laser (405 nm), respectively, for eight Schiff bases. These results will be reported elsewhere in due course, along with electrical conduction studies.

2. Structural commentary

As expected, all compounds crystallized in Sohncke space groups, namely P21 or P212121. The absolute configuration was determined from anomalous dispersion effects in two crystals, for chlorine and bromine compounds (5) and (6), confirming that the enanti­opure amines used as starting materials transfer the chiral center to the formed imines, without inversion. The Flack parameters for these crystals converged to 0.02 (6) and −0.009 (6), respectively. For the other compounds, the absolute configuration was assumed from the synthesis. Two compounds crystallize with four mol­ecules per asymmetric unit, (1) (Fig. 1[link]) and (8) (Fig. 6), while other compounds are obtained with a single mol­ecule in the asymmetric unit. All imines (1)–(8) bear a single chiral C atom (C12) presenting the S configuration, except for compounds (3) and (4), which are R isomers. The chiral center linking aromatic moieties in (1)–(7) induces a bent shape for these mol­ecules, and the dihedral angle formed by these moieties may be close to 90°. For instance, in the case of compound (2) (Fig. 2[link]), the naphthyl and benzene rings are inclined to one other at a dihedral angle of 80.49 (7)°

[Figure 1]
Figure 1
The asymmetric unit of (1), with displacement ellipsoids for non-H atoms at the 30% probability level. The labels for C atoms in mol­ecules N2, N3 and N4, are as in mol­ecule N1, but increased by 20, 40, and 60, respectively.
[Figure 2]
Figure 2
The mol­ecular structures of (2) (top) and (3) (bottom), with displacement ellipsoids for non-H atoms at the 30% probability level.

From the chemical point of view, compounds (1)–(6) are closely related (Figs. 1[link]–3[link][link]), by modification of the para substituent X of the phenyl group of phenyl­ethyl­amine. Since X is a monoatomic or a small, non-sterically demanding functional group, one could expect that it has no influence on the mol­ecular conformation. However, a fit between the conformers observed in (1)–(6) (Fig. 4[link]), shows that the benzene ring has a degree of free rotation about the C12—C14 bond. Such a conformational flexibility can be measured using the torsion angles around C12—C14 and dihedral angles between aromatic rings (Table 1[link]). Angles N1—C12—C14—C(ring) are in the range 97.9 (5) to 150.1 (5)° for the +anticlinal angle τ1, and in the range −33.7 (7) to −79.2 (6)° for −synclinal angle τ2. For the inter­planar dihedral angle δ, the observed range is from 43.7 (3) to 81.04 (11)°. Inter­estingly, (2), (5) and (6) have very similar metrics, probably as a consequence of the similar steric volumes for CH3, Cl, or Br groups. Angles τ1, τ2 and δ for (7) (Fig. 5[link]) and (8) (Fig. 6[link]) cannot be compared directly with values obtained for (1)–(6) because C12 is not substituted by a phenyl ring for these compounds (Table 1[link], entries 10–14).

Table 1
Relative orientation (°) between the naphthyl group and the ring bonded to the chiral C atom C12 in compounds (1)–(8)

Angles τ1 and τ2 are torsion angles N1—C12—C14—C(ring) or equivalent angles for compounds (1) and (8), which have four mol­ecules in the asymmetric unit. The dihedral angle δ is calculated between the mean planes of the naphthyl group and the ring bonded to C12.
Mol­ecule τ1 (+ac) τ2 (−sc) δ
(1)/N1 110.0 (5) −67.2 (5) 78.22 (11)
(1)/N2 140.7 (4) −41.5 (5) 58.23 (11)
(1)/N3 142.0 (4) −40.0 (6) 43.7 (3)
(1)/N4 110.0 (6) −64.6 (8) 74.97 (18)
(2) 98.3 (4) −77.7 (4) 80.49 (7)
(3)a 111.5 (5) −67.0 (6) 60.16 (13)
(4)a 150.1 (5) −33.7 (7) 45.91 (15)
(5) 97.9 (5) −77.9 (6) 80.99 (10)
(6) 98.1 (6) −79.2 (6) 81.04 (11)
       
(7)b 155.4 (3) −27.4 (4) 67.44 (6)
(8)/N1 60 (2) −66 (2) 88.6 (6)
(8)/N2 169.6 (9) −62.6 (12) 48.0 (3)
(8)/N3 70.0 (12) −55.6 (13) 88.2 (3)
(8)/N4 165.1 (14) 22 (3) 66.7 (6)
Notes: (a) Refined model has been inverted in order to compare S-C12 mol­ecules. (b) The dihedral angle δ is computed between the two naphthyl ring systems.
[Figure 3]
Figure 3
The mol­ecular structures of halogenated imines (4) (top), (5) (middle), and (6) (bottom), with displacement ellipsoids for non-H atoms at the 30% probability level. Note the different S/R configuration at C12 for (4) compared to (5) and (6).
[Figure 4]
Figure 4
A fit between mol­ecules (1)–(6), carried out using the naphthyl and imine group atoms (N1/C1–C11). The fit was calculated with the Structure Overlay command in Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), taking as a target the first independent mol­ecule in the first structure (1) (dark-gray mol­ecule). For compounds (3) and (4), the refined model was inverted, in order to fit only S-C12 isomers. Note the almost perfect fit obtained for (2), (5) and (6).
[Figure 5]
Figure 5
The mol­ecular structure of (7), with displacement ellipsoids for non-H atoms at the 30% probability level.
[Figure 6]
Figure 6
The asymmetric unit of (8), with displacement ellipsoids for non-H atoms at the 20% probability level. The labels for C atoms in mol­ecules N2, N3 and N4, are as in mol­ecule N1, but increased by 20, 40, and 60, respectively.

Finally, compounds (9) and (10) (Fig. 7[link]) are structurally different from (1)–(8), because the chiral center bonded to the imine group belongs to a cyclic system, introducing a strong restriction to the conformational flexibility.

[Figure 7]
Figure 7
The mol­ecular structures of (9) (top) and (10) (bottom), with displacement ellipsoids for non-H atoms at the 30% probability level.

It is worth noting that in all mol­ecular structures, the imine bond remains conjugated with the naphthyl group. Rotational motions are thus possible only around bonds N1—C12 and C12—C14 for (1)–(8). For (9) and (10), only one single bond is involved in conformational flexibility, N1—C12.

3. Supra­molecular features

A common feature may be observed over the series of crystal structures: despite the presence of aromatic systems, the mol­ecules are arranged in such a way that no π–π inter­actions are favored. As an example, in the case of (1), which crystallizes with four mol­ecules in the asymmetric unit, the mean planes of naphthyl groups stacked along [100] are separated by more than 6.5 Å. A consequence of the lack of stabilizing inter­molecular forces in these crystals is their quite low packing index, in the range 63.5 [for (8)] to 67.0% [for (10)], and the occurrence of asymmetric units containing multiple mol­ecules in the case of (1) and (8). For these compounds, the free rotation for the phenyl (1) or cyclo­hexyl (8) groups accounts for Z′ = 4 asymmetric units. Moreover, (1) and (8) crystallize in the same space group, P21, with similar unit-cell parameters, and similar arrangements for the mol­ecules in the crystal. In other words, the substitution of a planar phenyl group by a non-planar cyclo­hexyl group has little influence on the crystal structure.

The same kind of crystal structure similarity is observed for (2), (3), (5) and (6), where the benzene ring is para-substituted by non-sterically demanding functional groups, CH3, OCH3, Cl and Br, respectively. These four compounds crystallize in space group P212121 with unit-cell volumes of ca 1600 Å3 (see Table 2[link]). However, the F-based compound, (4), is not isomorphous to analoguous compounds bearing Cl (5) and Br (6). Again, this behavior may be related to the rotational freedom of the benzene ring, which modifies the mol­ecular conformation stabilized in the solid state.

Table 2
Experimental details

  (1) (2) (3)
Crystal data
Chemical formula C19H17N C20H19N C20H19NO
Mr 259.33 273.36 289.36
Crystal system, space group Monoclinic, P21 Orthorhombic, P212121 Orthorhombic, P212121
Temperature (K) 298 298 298
a, b, c (Å) 14.9328 (2), 6.01143 (10), 33.9985 (7) 6.0946 (5), 7.5732 (5), 34.046 (3) 6.1094 (5), 7.7266 (7), 34.225 (4)
α, β, γ (°) 90, 102.6011 (17), 90 90, 90, 90 90, 90, 90
V (Å3) 2978.45 (9) 1571.4 (2) 1615.6 (3)
Z 8 4 4
Radiation type Cu Kα Cu Kα Cu Kα
μ (mm−1) 0.51 0.51 0.57
Crystal size (mm) 0.49 × 0.17 × 0.10 0.49 × 0.13 × 0.05 0.39 × 0.25 × 0.23
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini
Absorption correction Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.862, 0.960 0.793, 0.969 0.777, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 33420, 10553, 9322 13738, 2770, 2048 14921, 3223, 1652
Rint 0.045 0.041 0.068
(sin θ/λ)max (Å−1) 0.622 0.595 0.624
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.092, 1.04 0.044, 0.112, 1.08 0.063, 0.155, 1.08
No. of reflections 10553 2770 3223
No. of parameters 722 192 201
No. of restraints 1 0 0
H-atom treatment H-atom parameters constrained H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.13, −0.12 0.09, −0.11 0.15, −0.20
  (4) (5) (6)
Crystal data
Chemical formula C19H16FN C19H16ClN C19H16BrN
Mr 277.33 293.78 338.24
Crystal system, space group Monoclinic, P21 Orthorhombic, P212121 Orthorhombic, P212121
Temperature (K) 298 298 298
a, b, c (Å) 7.5950 (11), 5.8997 (9), 16.996 (3) 6.0567 (5), 7.6139 (5), 33.853 (3) 6.0526 (2), 7.6671 (4), 33.9712 (19)
α, β, γ (°) 90, 99.420 (15), 90 90, 90, 90 90, 90, 90
V (Å3) 751.3 (2) 1561.1 (2) 1576.46 (13)
Z 2 4 4
Radiation type Mo Kα Mo Kα Mo Kα
μ (mm−1) 0.08 0.24 2.60
Crystal size (mm) 0.74 × 0.21 × 0.09 0.38 × 0.32 × 0.14 0.36 × 0.22 × 0.19
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini
Absorption correction Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.970, 0.994 0.437, 0.703 0.876, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections 7823, 2627, 1640 21167, 2752, 2014 19221, 3120, 2017
Rint 0.051 0.065 0.047
(sin θ/λ)max (Å−1) 0.595 0.595 0.618
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.153, 1.25 0.057, 0.139, 1.07 0.044, 0.098, 1.02
No. of reflections 2627 2752 3120
No. of parameters 190 191 191
No. of restraints 1 0 0
H-atom treatment H-atom parameters constrained H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.23, −0.19 0.18, −0.29 0.32, −0.44
Absolute structure – Flack x determined using 645 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]) Flack x determined using 643 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter – 0.02 (6) −0.009 (6)
  (7) (8)
Crystal data
Chemical formula C23H19N C19H23N
Mr 309.39 265.38
Crystal system, space group Monoclinic, P21 Monoclinic, P21
Temperature (K) 298 298
a, b, c (Å) 7.8555 (5), 7.8724 (4), 14.0494 (9) 15.406 (3), 5.9722 (7), 36.002 (7)
α, β, γ (°) 90, 99.859 (6), 90 90, 102.058 (18), 90
V (Å3) 856.01 (9) 3239.4 (10)
Z 2 8
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.07 0.06
Crystal size (mm) 0.45 × 0.35 × 0.11 0.54 × 0.09 × 0.07
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.921, 1.000 0.995, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections 9508, 3367, 2063 19804, 10600, 3810
Rint 0.043 0.119
(sin θ/λ)max (Å−1) 0.625 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.119, 1.01 0.078, 0.231, 0.99
No. of reflections 3367 10600
No. of parameters 218 727
No. of restraints 1 37
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.12, −0.14 0.23, −0.18
  (9) (10)
Crystal data
Chemical formula C21H19N C21H25N
Mr 285.37 291.42
Crystal system, space group Monoclinic, P21 Orthorhombic, P212121
Temperature (K) 298 150
a, b, c (Å) 7.7571 (13), 5.9246 (10), 17.820 (4) 6.32427 (18), 14.4559 (3), 18.5421 (5)
α, β, γ (°) 90, 92.682 (16), 90 90, 90, 90
V (Å3) 818.1 (2) 1695.17 (8)
Z 2 4
Radiation type Mo Kα Cu Kα
μ (mm−1) 0.07 0.49
Crystal size (mm) 0.88 × 0.43 × 0.08 0.40 × 0.15 × 0.12
 
Data collection
Diffractometer Agilent Xcalibur Atlas Gemini Agilent Xcalibur Atlas Gemini
Absorption correction Analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.857, 0.983 0.976, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 15266, 2884, 1822 19648, 3417, 2913
Rint 0.081 0.056
(sin θ/λ)max (Å−1) 0.595 0.624
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.175, 1.44 0.041, 0.103, 1.03
No. of reflections 2884 3417
No. of parameters 199 202
No. of restraints 1 0
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.21, −0.19 0.19, −0.17
Computer programs: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]), SHELXS2013 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and CifTab (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Indeed, the poor ability of the naphthyl group for the formation of π–π contacts seems to be a general rule. The crystal structures reported here cannot be compared to literature data, since no chiral secondary aldimine bearing a 2-naphthyl group on the C-side have been X-ray characterized up to now, and only a few cases are available with substituted naphthyl groups, generally related to BINOL derivatives (Li et al., 2004[Li, X.-S., Jia, X., Su, L.-M. & Zhou, Z.-Y. (2004). Acta Cryst. E60, o998-o999.]). However, small achiral Schiff bases including naphthyl (Blanco et al., 2012[Blanco, F., Egan, B., Caboni, L., Elguero, J., O'Brien, J., McCabe, T., Fayne, D., Meegan, M. J. & Lloyd, D. G. (2012). J. Chem. Inf. Model. 52, 2387-2397.]), or naphthol (Fernández-G et al., 1995[Fernández-G, J. M., Rodríguez-Romero, A., Panneerselvam, K. & Soriano-García, M. (1995). Acta Cryst. C51, 1643-1646.], 2001[Fernández-G, J. M., del Rio-Portilla, F., Quiroz-García, B., Toscano, R. A. & Salcedo, R. (2001). J. Mol. Struct. 561, 197-207.]; Martínez et al., 2011[Martínez, R. F., Ávalos, M., Babiano, R., Cintas, P., Jiménez, J. L., Light, M. E. & Palacios, J. C. (2011). Org. Biomol. Chem. 9, 8268-8275.]) have been reported. For these crystal structures, a general propensity to form C—H⋯π inter­molecular contacts rather than π–π contacts is observed.

4. Database survey

The structure of 2-naphthaldehyde was almost certainly determined but never reported. Neither are the crystal structures for the used amines available, since all are liquid at room temperature. Crystal structures for imines derived from 2-naphthaldehyde are also very scarce, and related to the chemistry of Schiff bases. Chiral 2-naphthaldehyde oxime derivatives have been synthesized as precursors of oxime ethers useful for the asymmetric synthesis of N-protected amines and β-amino acids (Hunt et al., 1999[Hunt, J. C. A., Lloyd, C., Moody, C. J., Slawin, A. M. Z. & Takle, A. K. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3443-3454.]). The structure of a radical compound bearing the 2-naphthyl­methyl­ene­amino group has also been determined (Iwasaki et al., 1999[Iwasaki, F., Yoshikawa, J. H., Yamamoto, H., Takada, K., Kan-nari, E., Yasui, M., Ishida, T. & Nogami, T. (1999). Acta Cryst. B55, 1057-1067.]), with the aim of rationalizing the ferromagnetic inter­actions in this compound, which presents a magnetic phase transition at 0.12 K (Ishida et al., 1995[Ishida, T., Tomioka, K., Nogami, T., Yoshikawa, H., Yasui, M., Iwasaki, F., Takeda, N. & Ishikawa, M. (1995). Chem. Phys. Lett. 247, 7-12.]). Finally, the structure of an hydrazide with the 2-naphthyl­methyl­ene group is known (Qiu et al., 2006[Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o3531-o3532.]).

Regarding imines built on the amines used in this work, X-ray structures have been deposited in the CSD (Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) for compounds derived from 1-phenyl­ethyl­amine [as for (1)] and 1-cyclo­hexyl­ethyl­amine [as in (8)]. For others, only sporadic X-ray determinations are carried out, for example for salicylaldimines (Enamullah et al., 2007[Enamullah, M., Uddin, A. K. M. R., Chamayou, A.-C. & Janiak, C. (2007). Z. Naturforsch. Teil B Chem. Sci. 62, 807-817.]). We thus think that there is room for improvement in the knowledge of the chemical crystallography of this class of compounds, taking into account that many of them are easy to prepare.

5. Synthesis and crystallization

The reaction of optically pure primary amines with 2-naphthaldehyde to yield chiral Schiff bases (1)–(10) was performed under solvent-free conditions. Reactants were mixed for 3–5 min. using a mortar and pestle, yielding oily products that become solids standing on air for an additional 2–3 minutes. The reaction was monitored by TLC and 1H NMR, observing the disappearance of the aldehyde. Because of the direct inter­action and because no excess of reagents were used, the products were obtained with no waste and no further purification processes were needed. In most cases the products were obtained in a sufficiently pure form, or a simple crystallization was enough, when necessary, and in our case, the obtained crude products were recrystallized from CH2Cl2, affording the corresponding pure Schiff bases (1)–(10) as crystals of good quality for X-ray studies.

The IR spectra (1)–(10) showed characteristic absorption bands in the 1635–1626 cm−1 range, due to the C=N stretching vibration, in agreement with reported values. In the 1H NMR spectra, the azomethine proton appears in the 8.33–8.51 p.p.m. range, while the imine bond is characterized in the 13C NMR spectra with the imine C signal in the 157.9–160.7 p.p.m. range. Full spectroscopic data are available in the supporting information.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Monoclinic crystals for compounds (1) and (8) were twinned by a twofold rotation, with the same twin law [[\overline{1}] 0 0, 0 [\overline{1}] 0, 1 0 1]. Twin weights are 0.42/0.58 for (1) and 0.11/0.89 for (8). Some structures [in particular (4), (8) and (9)] converged towards rather disappointing refinements, as a result of packing issues and disordered parts that were not well resolved. For (8), two cyclo­hexyl rings, C14–C19 and C74–C79, were restrained to have the same bond lengths as those of ring C34–C39. Other structures were refined without restraints.

For (1)–(9), H atoms were placed in idealized positions, with C—H bond lengths fixed at 0.93 (aromatic), 0.96 (meth­yl), 0.97 (methyl­ene) or 0.98 Å (methine). For (10), collected at 150 K, these distances were fixed at 0.95, 0.98, 0.99 and 1.00 Å, respectively. In all compounds, isotropic displacement parameters for H atoms were calculated as Uiso(H) = xUeq(carrier atom) with x = 1.5 (meth­yl) or x = 1.2 (methyl­ene, methine, aromatic).

Supporting information

CCDC references: 1425668; 1425667; 1425666; 1425665; 1425664; 1425663; 1425662; 1425661; 1425660; 1425659

Crystal structure: contains datablocks 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, global. DOI: https://doi.org/10.1107/S2056989016004692/hb7571sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989016004692/hb75711sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989016004692/hb75712sup3.hkl

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989016004692/hb75713sup4.hkl

Structure factors: contains datablock 4. DOI: https://doi.org/10.1107/S2056989016004692/hb75714sup5.hkl

Structure factors: contains datablock 5. DOI: https://doi.org/10.1107/S2056989016004692/hb75715sup6.hkl

Structure factors: contains datablock 6. DOI: https://doi.org/10.1107/S2056989016004692/hb75716sup7.hkl

Structure factors: contains datablock 7. DOI: https://doi.org/10.1107/S2056989016004692/hb75717sup8.hkl

Structure factors: contains datablock 8. DOI: https://doi.org/10.1107/S2056989016004692/hb75718sup9.hkl

Structure factors: contains datablock 9. DOI: https://doi.org/10.1107/S2056989016004692/hb75719sup10.hkl

Structure factors: contains datablock 10. DOI: https://doi.org/10.1107/S2056989016004692/hb757110sup11.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75711sup12.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75712sup13.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75713sup14.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75714sup15.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75715sup16.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75716sup17.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75717sup18.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75718sup19.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb75719sup20.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb757110sup21.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016004692/hb7571sup22.pdf

checkCIF report


Computing details top

For all compounds, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CifTab (Sheldrick, 2015).

(1) (S)-(+)-2-{[(1-Phenylethyl)imino]methyl}naphthalene top
Crystal data top
C19H17NDx = 1.157 Mg m−3
Mr = 259.33Melting point: 389 K
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 14.9328 (2) ÅCell parameters from 11908 reflections
b = 6.01143 (10) Åθ = 3.6–74.0°
c = 33.9985 (7) ŵ = 0.51 mm−1
β = 102.6011 (17)°T = 298 K
V = 2978.45 (9) Å3Prism, colorless
Z = 80.49 × 0.17 × 0.10 mm
F(000) = 1104
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		10553 independent reflections
Radiation source: Enhance (Cu) X-ray Source9322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 10.5564 pixels mm-1θmax = 73.7°, θmin = 3.0°
ω scansh = −18→18
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −7→6
Tmin = 0.862, Tmax = 0.960l = −42→42
33420 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0357P)2 + 0.0936P]
where P = (Fo2 + 2Fc2)/3
10553 reflections(Δ/σ)max < 0.001
722 parametersΔρmax = 0.13 e Å−3
1 restraintΔρmin = −0.12 e Å−3
0 constraints
Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3821 (2)0.6149 (7)0.12375 (10)0.0691 (8)
C10.36179 (19)0.5467 (6)0.05277 (10)0.0517 (7)
C20.33602 (19)0.6359 (5)0.01504 (10)0.0489 (6)
H2A0.30790.77470.01180.059*
C30.35134 (18)0.5212 (5)−0.01922 (10)0.0484 (6)
C40.3294 (2)0.6113 (6)−0.05836 (12)0.0587 (8)
H4A0.29960.7479−0.06260.070*
C50.3509 (3)0.5030 (8)−0.09004 (11)0.0693 (10)
H5A0.33670.5671−0.11550.083*
C60.3945 (3)0.2943 (9)−0.08457 (14)0.0726 (11)
H6A0.41010.2218−0.10630.087*
C70.4139 (2)0.1987 (7)−0.04728 (13)0.0654 (9)
H7A0.44090.0586−0.04410.078*
C80.39396 (18)0.3070 (6)−0.01371 (11)0.0518 (7)
C90.4167 (2)0.2169 (6)0.02562 (12)0.0571 (8)
H9A0.44250.07570.02940.069*
C100.4016 (2)0.3322 (6)0.05801 (11)0.0567 (7)
H10A0.41750.26990.08360.068*
C110.3529 (2)0.6828 (7)0.08803 (10)0.0572 (8)
H11A0.32500.82170.08380.069*
C120.3764 (3)0.7728 (10)0.15620 (13)0.0813 (13)
H12A0.34920.91260.14440.098*
C130.3142 (3)0.6688 (17)0.18172 (17)0.125 (3)
H13A0.30920.76840.20320.188*
H13B0.25440.64250.16510.188*
H13C0.34020.53040.19280.188*
C140.4726 (3)0.8153 (8)0.17974 (11)0.0680 (9)
C150.5234 (3)0.6523 (9)0.20243 (13)0.0803 (11)
H15A0.49650.51370.20380.096*
C160.6118 (4)0.6838 (14)0.22324 (16)0.104 (2)
H16A0.64370.56940.23870.125*
C170.6526 (4)0.8840 (14)0.2211 (2)0.111 (2)
H17A0.71290.90700.23480.133*
C180.6054 (5)1.0499 (14)0.1989 (2)0.116 (2)
H18A0.63331.18710.19760.140*
C190.5146 (4)1.0165 (10)0.17805 (16)0.0916 (13)
H19A0.48271.13180.16290.110*
N20.8709 (2)0.5109 (6)0.10287 (9)0.0609 (7)
C210.86187 (19)0.5227 (6)0.03158 (9)0.0477 (6)
C220.83652 (18)0.6499 (6)−0.00250 (9)0.0472 (6)
H22A0.80840.7867−0.00100.057*
C230.85254 (19)0.5763 (6)−0.04015 (10)0.0473 (7)
C240.8294 (2)0.7087 (7)−0.07530 (11)0.0587 (8)
H24A0.80120.8460−0.07440.070*
C250.8484 (3)0.6352 (9)−0.11067 (11)0.0713 (10)
H25A0.83270.7227−0.13370.086*
C260.8913 (3)0.4295 (9)−0.11252 (11)0.0713 (10)
H26A0.90450.3823−0.13670.086*
C270.9137 (2)0.2985 (7)−0.07933 (12)0.0611 (8)
H27A0.94180.1620−0.08100.073*
C280.89465 (18)0.3671 (6)−0.04203 (10)0.0491 (7)
C290.9181 (2)0.2384 (6)−0.00648 (11)0.0527 (7)
H29A0.94450.0991−0.00750.063*
C300.9028 (2)0.3138 (6)0.02941 (10)0.0523 (7)
H30A0.91940.22670.05240.063*
C310.8472 (2)0.6129 (6)0.07003 (10)0.0505 (7)
H31A0.81920.75110.06990.061*
C320.8530 (3)0.6215 (8)0.13915 (10)0.0645 (9)
H32A0.82280.76450.13140.077*
C330.7889 (3)0.4731 (11)0.15689 (12)0.0841 (13)
H33A0.77640.54200.18060.126*
H33B0.73250.45250.13740.126*
H33C0.81760.33130.16390.126*
C340.9416 (2)0.6614 (7)0.16909 (9)0.0612 (8)
C350.9537 (4)0.8582 (9)0.19069 (13)0.0822 (11)
H35A0.90760.96510.18610.099*
C361.0340 (4)0.8977 (11)0.21920 (14)0.0984 (16)
H36A1.04141.03130.23330.118*
C371.1019 (4)0.7420 (12)0.22665 (14)0.0954 (17)
H37A1.15540.76850.24590.115*
C381.0906 (3)0.5450 (10)0.20537 (13)0.0819 (12)
H38A1.13690.43840.21020.098*
C391.0103 (3)0.5050 (8)0.17674 (11)0.0670 (9)
H39A1.00300.37130.16260.080*
N30.7737 (2)0.5492 (6)0.39508 (9)0.0652 (7)
C410.8320 (2)0.5196 (6)0.46632 (10)0.0507 (7)
C420.8391 (2)0.3881 (6)0.49968 (10)0.0497 (6)
H42A0.80970.25080.49720.060*
C430.89007 (19)0.4564 (5)0.53793 (10)0.0487 (7)
C440.8999 (2)0.3201 (7)0.57233 (11)0.0590 (8)
H44A0.87040.18300.57040.071*
C450.9519 (3)0.3873 (9)0.60815 (12)0.0748 (11)
H45A0.95780.29570.63060.090*
C460.9970 (3)0.5927 (9)0.61173 (12)0.0740 (11)
H46A1.03350.63500.63640.089*
C470.9877 (2)0.7321 (7)0.57922 (12)0.0614 (8)
H47A1.01670.87000.58210.074*
C480.9341 (2)0.6669 (6)0.54124 (10)0.0512 (7)
C490.9242 (2)0.8019 (6)0.50660 (11)0.0545 (7)
H49A0.95160.94150.50860.065*
C500.8751 (2)0.7305 (6)0.47012 (10)0.0540 (7)
H50A0.86990.82130.44760.065*
C510.7827 (2)0.4360 (7)0.42688 (11)0.0556 (8)
H51A0.75710.29440.42540.067*
C520.7257 (3)0.4463 (9)0.35727 (11)0.0717 (10)
H52A0.70920.29280.36230.086*
C530.6389 (3)0.5813 (15)0.34092 (14)0.107 (2)
H53A0.60620.51680.31610.161*
H53B0.60050.58020.36020.161*
H53C0.65530.73180.33620.161*
C540.7881 (2)0.4484 (7)0.32731 (10)0.0625 (8)
C550.7900 (3)0.2742 (9)0.30191 (13)0.0816 (11)
H55A0.75370.15000.30330.098*
C560.8453 (4)0.2788 (11)0.27403 (14)0.0933 (16)
H56A0.84620.15700.25730.112*
C570.8982 (3)0.4596 (12)0.27090 (13)0.0930 (16)
H57A0.93460.46330.25190.112*
C580.8966 (3)0.6345 (11)0.29607 (13)0.0908 (14)
H58A0.93260.75890.29430.109*
C590.8428 (3)0.6304 (9)0.32411 (13)0.0800 (11)
H59A0.84310.75150.34120.096*
N40.2651 (2)0.3804 (7)0.37650 (10)0.0689 (8)
C610.3102 (2)0.4677 (6)0.44685 (11)0.0517 (7)
C620.3211 (2)0.3891 (6)0.48543 (10)0.0506 (7)
H62A0.29690.25090.48970.061*
C630.3682 (2)0.5138 (6)0.51895 (10)0.0520 (7)
C640.3834 (3)0.4321 (7)0.55866 (12)0.0627 (8)
H64A0.35820.29630.56370.075*
C650.4350 (3)0.5507 (10)0.59009 (12)0.0786 (12)
H65A0.44550.49430.61620.094*
C660.4716 (3)0.7560 (10)0.58280 (15)0.0811 (13)
H66A0.50740.83430.60420.097*
C670.4561 (2)0.8437 (7)0.54536 (14)0.0688 (10)
H67A0.47940.98340.54140.083*
C680.4040 (2)0.7234 (6)0.51177 (12)0.0561 (8)
C690.3902 (2)0.8050 (6)0.47211 (12)0.0608 (8)
H69A0.41230.94500.46750.073*
C700.3452 (2)0.6821 (6)0.44050 (11)0.0587 (8)
H70A0.33700.73820.41450.070*
C710.2688 (2)0.3262 (7)0.41287 (11)0.0579 (8)
H71A0.24410.19020.41810.069*
C720.2241 (3)0.2199 (10)0.34534 (12)0.0836 (13)
H72A0.20530.08780.35840.100*
C730.1402 (4)0.3254 (17)0.31912 (17)0.121 (2)
H73A0.11230.22250.29850.182*
H73B0.09720.36300.33530.182*
H73C0.15780.45770.30690.182*
C740.2959 (4)0.1528 (9)0.32225 (12)0.0798 (11)
C750.3347 (5)−0.0576 (13)0.32531 (17)0.1092 (19)
H75A0.3136−0.16480.34080.131*
C760.4044 (6)−0.1128 (17)0.3057 (3)0.132 (3)
H76A0.4299−0.25460.30870.158*
C770.4352 (6)0.0374 (18)0.2825 (2)0.131 (3)
H77A0.48070.00010.26890.157*
C780.3987 (8)0.2431 (19)0.2795 (3)0.151 (4)
H78A0.41920.34840.26340.181*
C790.3318 (7)0.3004 (16)0.2996 (2)0.136 (3)
H79A0.31020.44590.29770.164*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0601 (15)0.077 (2)0.0677 (17)−0.0013 (15)0.0091 (13)−0.0007 (16)
C10.0347 (12)0.0521 (18)0.0677 (18)−0.0048 (12)0.0099 (12)0.0009 (15)
C20.0362 (12)0.0388 (15)0.0698 (17)0.0004 (12)0.0072 (12)−0.0024 (14)
C30.0333 (12)0.0418 (16)0.0692 (17)−0.0062 (11)0.0094 (11)−0.0010 (14)
C40.0510 (15)0.052 (2)0.0708 (19)−0.0034 (15)0.0091 (14)0.0035 (16)
C50.0639 (19)0.080 (3)0.0636 (18)−0.0076 (19)0.0139 (15)−0.0013 (18)
C60.0554 (17)0.084 (3)0.081 (2)−0.0093 (19)0.0214 (16)−0.022 (2)
C70.0431 (14)0.058 (2)0.096 (3)0.0009 (14)0.0172 (14)−0.0174 (19)
C80.0314 (11)0.0428 (16)0.0807 (19)−0.0057 (11)0.0109 (11)−0.0042 (15)
C90.0411 (13)0.0373 (16)0.091 (2)0.0020 (12)0.0097 (13)0.0071 (16)
C100.0430 (13)0.0550 (19)0.0700 (17)−0.0026 (13)0.0073 (12)0.0120 (16)
C110.0434 (13)0.064 (2)0.0633 (17)−0.0009 (14)0.0092 (12)−0.0011 (16)
C120.070 (2)0.107 (4)0.066 (2)0.015 (2)0.0116 (16)−0.010 (2)
C130.072 (2)0.218 (9)0.092 (3)−0.019 (4)0.031 (2)−0.021 (5)
C140.0732 (19)0.081 (3)0.0526 (15)0.0040 (19)0.0188 (14)−0.0093 (17)
C150.077 (2)0.087 (3)0.074 (2)0.008 (2)0.0121 (18)−0.006 (2)
C160.085 (3)0.140 (6)0.081 (3)0.026 (4)0.002 (2)−0.019 (3)
C170.086 (3)0.138 (6)0.107 (4)−0.006 (4)0.014 (3)−0.051 (4)
C180.121 (5)0.111 (5)0.123 (4)−0.043 (4)0.039 (4)−0.039 (4)
C190.111 (3)0.086 (3)0.080 (3)−0.005 (3)0.026 (2)−0.006 (2)
N20.0652 (15)0.0618 (19)0.0551 (13)0.0062 (14)0.0121 (11)0.0011 (13)
C210.0358 (11)0.0485 (17)0.0584 (15)−0.0045 (12)0.0096 (11)−0.0025 (14)
C220.0382 (12)0.0427 (15)0.0620 (16)0.0049 (12)0.0139 (11)−0.0005 (13)
C230.0336 (11)0.0522 (18)0.0564 (15)−0.0022 (11)0.0102 (11)−0.0021 (13)
C240.0537 (15)0.059 (2)0.0645 (17)0.0071 (15)0.0160 (13)0.0081 (16)
C250.070 (2)0.088 (3)0.0585 (17)0.006 (2)0.0205 (15)0.0104 (19)
C260.071 (2)0.088 (3)0.0589 (18)0.004 (2)0.0230 (15)−0.0137 (19)
C270.0509 (15)0.063 (2)0.0704 (19)0.0080 (16)0.0159 (14)−0.0114 (18)
C280.0344 (11)0.0513 (18)0.0617 (15)−0.0037 (12)0.0103 (11)−0.0103 (14)
C290.0395 (12)0.0425 (16)0.0752 (18)0.0043 (12)0.0107 (12)−0.0061 (14)
C300.0420 (12)0.0513 (18)0.0615 (15)−0.0025 (13)0.0067 (11)0.0039 (14)
C310.0452 (13)0.0489 (18)0.0577 (16)0.0015 (12)0.0120 (12)−0.0003 (14)
C320.0684 (18)0.073 (2)0.0526 (15)0.0123 (17)0.0146 (14)0.0010 (16)
C330.067 (2)0.118 (4)0.069 (2)0.001 (2)0.0188 (16)0.005 (2)
C340.0719 (18)0.066 (2)0.0499 (14)0.0010 (16)0.0222 (13)0.0059 (14)
C350.100 (3)0.078 (3)0.070 (2)0.002 (2)0.020 (2)−0.006 (2)
C360.118 (4)0.102 (4)0.073 (2)−0.027 (3)0.018 (3)−0.019 (3)
C370.086 (3)0.129 (5)0.067 (2)−0.033 (3)0.0081 (19)0.006 (3)
C380.0641 (19)0.108 (4)0.074 (2)0.001 (2)0.0160 (17)0.018 (2)
C390.0649 (17)0.076 (2)0.0631 (17)−0.0012 (18)0.0197 (14)0.0042 (17)
N30.0677 (16)0.071 (2)0.0580 (15)−0.0017 (15)0.0175 (12)−0.0013 (14)
C410.0413 (13)0.0545 (18)0.0588 (16)0.0012 (13)0.0166 (11)−0.0020 (14)
C420.0425 (13)0.0440 (15)0.0646 (16)−0.0014 (12)0.0159 (12)−0.0032 (14)
C430.0388 (13)0.0463 (17)0.0631 (17)0.0032 (12)0.0157 (12)0.0002 (14)
C440.0535 (15)0.0554 (19)0.0695 (19)0.0018 (14)0.0166 (13)0.0063 (16)
C450.073 (2)0.087 (3)0.0613 (18)0.003 (2)0.0094 (16)0.014 (2)
C460.0618 (18)0.093 (3)0.0635 (18)−0.001 (2)0.0047 (15)−0.004 (2)
C470.0519 (16)0.061 (2)0.072 (2)−0.0042 (16)0.0135 (14)−0.0123 (17)
C480.0424 (13)0.0504 (17)0.0641 (16)0.0028 (12)0.0189 (11)−0.0064 (14)
C490.0507 (14)0.0435 (16)0.0741 (19)−0.0032 (13)0.0240 (14)−0.0026 (15)
C500.0549 (15)0.0520 (18)0.0598 (16)0.0016 (14)0.0226 (13)0.0060 (14)
C510.0457 (14)0.062 (2)0.0612 (17)−0.0011 (14)0.0164 (13)−0.0012 (16)
C520.070 (2)0.088 (3)0.0584 (17)−0.012 (2)0.0151 (15)−0.0020 (19)
C530.069 (2)0.181 (7)0.073 (2)0.013 (3)0.0195 (18)0.002 (3)
C540.0586 (16)0.076 (2)0.0503 (14)−0.0027 (16)0.0062 (12)0.0018 (15)
C550.081 (2)0.090 (3)0.073 (2)−0.014 (2)0.0142 (18)−0.011 (2)
C560.089 (3)0.119 (5)0.073 (2)−0.005 (3)0.021 (2)−0.031 (3)
C570.067 (2)0.154 (5)0.0576 (18)0.002 (3)0.0134 (16)0.001 (3)
C580.083 (2)0.122 (4)0.071 (2)−0.029 (3)0.0226 (18)0.003 (3)
C590.082 (2)0.088 (3)0.073 (2)−0.015 (2)0.0221 (18)−0.007 (2)
N40.0760 (18)0.070 (2)0.0617 (16)−0.0039 (16)0.0165 (14)0.0041 (15)
C610.0439 (13)0.0472 (17)0.0668 (18)0.0027 (13)0.0185 (13)0.0023 (14)
C620.0434 (13)0.0412 (15)0.0704 (18)0.0001 (12)0.0194 (13)0.0018 (14)
C630.0406 (13)0.0502 (19)0.0692 (17)0.0036 (13)0.0208 (12)0.0000 (14)
C640.0589 (17)0.062 (2)0.069 (2)−0.0008 (16)0.0190 (15)−0.0039 (17)
C650.077 (2)0.096 (3)0.0624 (19)0.009 (2)0.0164 (17)−0.007 (2)
C660.0578 (19)0.097 (4)0.089 (3)−0.009 (2)0.0176 (18)−0.034 (3)
C670.0538 (16)0.062 (2)0.095 (3)−0.0091 (16)0.0258 (17)−0.019 (2)
C680.0392 (13)0.0497 (19)0.084 (2)0.0008 (13)0.0229 (13)−0.0095 (16)
C690.0547 (16)0.0414 (18)0.092 (2)0.0024 (14)0.0279 (16)0.0087 (17)
C700.0533 (15)0.055 (2)0.0707 (19)0.0037 (15)0.0203 (13)0.0101 (16)
C710.0479 (15)0.059 (2)0.0685 (19)−0.0018 (14)0.0158 (13)0.0034 (17)
C720.090 (3)0.101 (4)0.0569 (18)−0.022 (3)0.0116 (18)−0.005 (2)
C730.095 (3)0.177 (7)0.082 (3)0.009 (4)−0.001 (3)−0.005 (4)
C740.098 (3)0.082 (3)0.0578 (18)−0.015 (2)0.0135 (18)−0.0021 (19)
C750.122 (4)0.119 (5)0.083 (3)0.001 (4)0.016 (3)0.018 (3)
C760.121 (5)0.137 (7)0.135 (5)0.028 (5)0.026 (4)−0.011 (5)
C770.137 (5)0.166 (8)0.103 (4)−0.005 (5)0.053 (4)−0.029 (5)
C780.185 (8)0.155 (8)0.141 (6)0.006 (7)0.098 (7)0.022 (6)
C790.171 (7)0.122 (6)0.142 (6)0.011 (5)0.091 (6)0.031 (5)
Geometric parameters (Å, º) top
N1—C111.265 (5)N3—C511.260 (5)
N1—C121.472 (6)N3—C521.465 (5)
C1—C21.366 (5)C41—C421.368 (5)
C1—C101.415 (5)C41—C501.415 (5)
C1—C111.481 (5)C41—C511.470 (5)
C2—C31.414 (5)C42—C431.417 (5)
C2—H2A0.9300C42—H42A0.9300
C3—C41.407 (5)C43—C441.409 (5)
C3—C81.430 (5)C43—C481.420 (5)
C4—C51.355 (6)C44—C451.356 (6)
C4—H4A0.9300C44—H44A0.9300
C5—C61.408 (7)C45—C461.399 (7)
C5—H5A0.9300C45—H45A0.9300
C6—C71.364 (7)C46—C471.370 (6)
C6—H6A0.9300C46—H46A0.9300
C7—C81.401 (5)C47—C481.418 (5)
C7—H7A0.9300C47—H47A0.9300
C8—C91.414 (5)C48—C491.411 (5)
C9—C101.361 (6)C49—C501.365 (5)
C9—H9A0.9300C49—H49A0.9300
C10—H10A0.9300C50—H50A0.9300
C11—H11A0.9300C51—H51A0.9300
C12—C141.506 (6)C52—C541.523 (5)
C12—C131.535 (8)C52—C531.528 (8)
C12—H12A0.9800C52—H52A0.9800
C13—H13A0.9600C53—H53A0.9600
C13—H13B0.9600C53—H53B0.9600
C13—H13C0.9600C53—H53C0.9600
C14—C151.370 (7)C54—C551.362 (6)
C14—C191.370 (7)C54—C591.384 (6)
C15—C161.369 (8)C55—C561.386 (7)
C15—H15A0.9300C55—H55A0.9300
C16—C171.358 (11)C56—C571.361 (9)
C16—H16A0.9300C56—H56A0.9300
C17—C181.352 (11)C57—C581.359 (9)
C17—H17A0.9300C57—H57A0.9300
C18—C191.401 (9)C58—C591.375 (6)
C18—H18A0.9300C58—H58A0.9300
C19—H19A0.9300C59—H59A0.9300
N2—C311.255 (5)N4—C711.268 (5)
N2—C321.476 (5)N4—C721.464 (6)
C21—C221.371 (5)C61—C621.370 (5)
C21—C301.405 (5)C61—C701.425 (5)
C21—C311.475 (4)C61—C711.459 (5)
C22—C231.423 (4)C62—C631.417 (5)
C22—H22A0.9300C62—H62A0.9300
C23—C281.413 (5)C63—C641.408 (5)
C23—C241.415 (5)C63—C681.410 (5)
C24—C251.368 (5)C64—C651.373 (6)
C24—H24A0.9300C64—H64A0.9300
C25—C261.400 (7)C65—C661.393 (8)
C25—H25A0.9300C65—H65A0.9300
C26—C271.357 (6)C66—C671.350 (7)
C26—H26A0.9300C66—H66A0.9300
C27—C281.420 (5)C67—C681.429 (6)
C27—H27A0.9300C67—H67A0.9300
C28—C291.413 (5)C68—C691.407 (6)
C29—C301.367 (5)C69—C701.356 (6)
C29—H29A0.9300C69—H69A0.9300
C30—H30A0.9300C70—H70A0.9300
C31—H31A0.9300C71—H71A0.9300
C32—C341.502 (5)C72—C731.510 (8)
C32—C331.525 (6)C72—C741.515 (7)
C32—H32A0.9800C72—H72A0.9800
C33—H33A0.9600C73—H73A0.9600
C33—H33B0.9600C73—H73B0.9600
C33—H33C0.9600C73—H73C0.9600
C34—C391.374 (6)C74—C791.359 (9)
C34—C351.383 (6)C74—C751.385 (9)
C35—C361.388 (8)C75—C761.394 (11)
C35—H35A0.9300C75—H75A0.9300
C36—C371.363 (10)C76—C771.344 (12)
C36—H36A0.9300C76—H76A0.9300
C37—C381.379 (8)C77—C781.346 (13)
C37—H37A0.9300C77—H77A0.9300
C38—C391.391 (6)C78—C791.373 (11)
C38—H38A0.9300C78—H78A0.9300
C39—H39A0.9300C79—H79A0.9300
C11—N1—C12116.5 (4)C51—N3—C52117.7 (4)
C2—C1—C10120.0 (3)C42—C41—C50119.4 (3)
C2—C1—C11119.1 (3)C42—C41—C51119.5 (3)
C10—C1—C11120.7 (3)C50—C41—C51121.1 (3)
C1—C2—C3121.3 (3)C41—C42—C43121.5 (3)
C1—C2—H2A119.4C41—C42—H42A119.2
C3—C2—H2A119.4C43—C42—H42A119.2
C4—C3—C2123.0 (3)C44—C43—C42122.1 (3)
C4—C3—C8118.4 (3)C44—C43—C48119.3 (3)
C2—C3—C8118.6 (3)C42—C43—C48118.6 (3)
C5—C4—C3121.3 (4)C45—C44—C43120.5 (4)
C5—C4—H4A119.3C45—C44—H44A119.7
C3—C4—H4A119.3C43—C44—H44A119.7
C4—C5—C6120.4 (4)C44—C45—C46120.8 (4)
C4—C5—H5A119.8C44—C45—H45A119.6
C6—C5—H5A119.8C46—C45—H45A119.6
C7—C6—C5119.8 (4)C47—C46—C45120.5 (4)
C7—C6—H6A120.1C47—C46—H46A119.7
C5—C6—H6A120.1C45—C46—H46A119.7
C6—C7—C8121.4 (4)C46—C47—C48120.2 (4)
C6—C7—H7A119.3C46—C47—H47A119.9
C8—C7—H7A119.3C48—C47—H47A119.9
C7—C8—C9122.9 (3)C49—C48—C47122.4 (3)
C7—C8—C3118.6 (3)C49—C48—C43118.9 (3)
C9—C8—C3118.5 (3)C47—C48—C43118.6 (3)
C10—C9—C8121.5 (3)C50—C49—C48121.0 (3)
C10—C9—H9A119.3C50—C49—H49A119.5
C8—C9—H9A119.3C48—C49—H49A119.5
C9—C10—C1120.1 (3)C49—C50—C41120.5 (3)
C9—C10—H10A120.0C49—C50—H50A119.7
C1—C10—H10A120.0C41—C50—H50A119.7
N1—C11—C1121.7 (4)N3—C51—C41122.4 (3)
N1—C11—H11A119.1N3—C51—H51A118.8
C1—C11—H11A119.1C41—C51—H51A118.8
N1—C12—C14107.6 (3)N3—C52—C54109.3 (3)
N1—C12—C13107.6 (5)N3—C52—C53108.0 (4)
C14—C12—C13113.1 (4)C54—C52—C53110.3 (3)
N1—C12—H12A109.5N3—C52—H52A109.8
C14—C12—H12A109.5C54—C52—H52A109.8
C13—C12—H12A109.5C53—C52—H52A109.8
C12—C13—H13A109.5C52—C53—H53A109.5
C12—C13—H13B109.5C52—C53—H53B109.5
H13A—C13—H13B109.5H53A—C53—H53B109.5
C12—C13—H13C109.5C52—C53—H53C109.5
H13A—C13—H13C109.5H53A—C53—H53C109.5
H13B—C13—H13C109.5H53B—C53—H53C109.5
C15—C14—C19116.9 (5)C55—C54—C59117.6 (4)
C15—C14—C12121.6 (5)C55—C54—C52121.3 (4)
C19—C14—C12121.4 (5)C59—C54—C52121.1 (4)
C16—C15—C14123.1 (6)C54—C55—C56121.1 (5)
C16—C15—H15A118.5C54—C55—H55A119.4
C14—C15—H15A118.5C56—C55—H55A119.4
C17—C16—C15119.2 (6)C57—C56—C55120.8 (5)
C17—C16—H16A120.4C57—C56—H56A119.6
C15—C16—H16A120.4C55—C56—H56A119.6
C18—C17—C16119.9 (6)C58—C57—C56118.6 (4)
C18—C17—H17A120.0C58—C57—H57A120.7
C16—C17—H17A120.0C56—C57—H57A120.7
C17—C18—C19120.4 (6)C57—C58—C59121.0 (5)
C17—C18—H18A119.8C57—C58—H58A119.5
C19—C18—H18A119.8C59—C58—H58A119.5
C14—C19—C18120.5 (6)C58—C59—C54120.9 (5)
C14—C19—H19A119.8C58—C59—H59A119.6
C18—C19—H19A119.8C54—C59—H59A119.6
C31—N2—C32117.1 (3)C71—N4—C72117.3 (4)
C22—C21—C30119.8 (3)C62—C61—C70119.1 (3)
C22—C21—C31118.5 (3)C62—C61—C71119.9 (3)
C30—C21—C31121.7 (3)C70—C61—C71120.9 (3)
C21—C22—C23121.1 (3)C61—C62—C63121.5 (3)
C21—C22—H22A119.4C61—C62—H62A119.3
C23—C22—H22A119.4C63—C62—H62A119.3
C28—C23—C24119.4 (3)C64—C63—C68119.3 (4)
C28—C23—C22118.8 (3)C64—C63—C62122.3 (4)
C24—C23—C22121.8 (3)C68—C63—C62118.3 (3)
C25—C24—C23120.1 (4)C65—C64—C63120.7 (4)
C25—C24—H24A119.9C65—C64—H64A119.7
C23—C24—H24A119.9C63—C64—H64A119.7
C24—C25—C26120.6 (4)C64—C65—C66119.8 (4)
C24—C25—H25A119.7C64—C65—H65A120.1
C26—C25—H25A119.7C66—C65—H65A120.1
C27—C26—C25120.5 (3)C67—C66—C65121.3 (4)
C27—C26—H26A119.7C67—C66—H66A119.3
C25—C26—H26A119.7C65—C66—H66A119.3
C26—C27—C28120.9 (4)C66—C67—C68120.5 (4)
C26—C27—H27A119.6C66—C67—H67A119.8
C28—C27—H27A119.6C68—C67—H67A119.8
C29—C28—C23118.5 (3)C69—C68—C63119.7 (3)
C29—C28—C27123.0 (3)C69—C68—C67122.0 (4)
C23—C28—C27118.4 (3)C63—C68—C67118.3 (4)
C30—C29—C28121.6 (3)C70—C69—C68120.9 (3)
C30—C29—H29A119.2C70—C69—H69A119.6
C28—C29—H29A119.2C68—C69—H69A119.6
C29—C30—C21120.2 (3)C69—C70—C61120.5 (3)
C29—C30—H30A119.9C69—C70—H70A119.7
C21—C30—H30A119.9C61—C70—H70A119.7
N2—C31—C21122.8 (3)N4—C71—C61122.9 (4)
N2—C31—H31A118.6N4—C71—H71A118.6
C21—C31—H31A118.6C61—C71—H71A118.6
N2—C32—C34110.2 (3)N4—C72—C73108.2 (5)
N2—C32—C33108.1 (4)N4—C72—C74108.6 (4)
C34—C32—C33111.2 (3)C73—C72—C74113.3 (4)
N2—C32—H32A109.1N4—C72—H72A108.9
C34—C32—H32A109.1C73—C72—H72A108.9
C33—C32—H32A109.1C74—C72—H72A108.9
C32—C33—H33A109.5C72—C73—H73A109.5
C32—C33—H33B109.5C72—C73—H73B109.5
H33A—C33—H33B109.5H73A—C73—H73B109.5
C32—C33—H33C109.5C72—C73—H73C109.5
H33A—C33—H33C109.5H73A—C73—H73C109.5
H33B—C33—H33C109.5H73B—C73—H73C109.5
C39—C34—C35118.6 (4)C79—C74—C75115.4 (6)
C39—C34—C32122.0 (4)C79—C74—C72122.1 (6)
C35—C34—C32119.3 (4)C75—C74—C72122.4 (5)
C34—C35—C36120.6 (5)C74—C75—C76121.7 (7)
C34—C35—H35A119.7C74—C75—H75A119.2
C36—C35—H35A119.7C76—C75—H75A119.2
C37—C36—C35120.5 (5)C77—C76—C75120.5 (8)
C37—C36—H36A119.8C77—C76—H76A119.8
C35—C36—H36A119.8C75—C76—H76A119.8
C36—C37—C38119.4 (5)C76—C77—C78118.6 (7)
C36—C37—H37A120.3C76—C77—H77A120.7
C38—C37—H37A120.3C78—C77—H77A120.7
C37—C38—C39120.2 (5)C77—C78—C79121.2 (8)
C37—C38—H38A119.9C77—C78—H78A119.4
C39—C38—H38A119.9C79—C78—H78A119.4
C34—C39—C38120.6 (4)C74—C79—C78122.6 (9)
C34—C39—H39A119.7C74—C79—H79A118.7
C38—C39—H39A119.7C78—C79—H79A118.7
C10—C1—C2—C3−2.4 (4)C50—C41—C42—C43−1.2 (5)
C11—C1—C2—C3173.9 (3)C51—C41—C42—C43176.6 (3)
C1—C2—C3—C4−177.2 (3)C41—C42—C43—C44−178.3 (3)
C1—C2—C3—C80.6 (4)C41—C42—C43—C480.3 (4)
C2—C3—C4—C5175.4 (3)C42—C43—C44—C45177.6 (3)
C8—C3—C4—C5−2.4 (5)C48—C43—C44—C45−1.0 (5)
C3—C4—C5—C61.2 (6)C43—C44—C45—C460.0 (6)
C4—C5—C6—C71.1 (6)C44—C45—C46—C471.4 (7)
C5—C6—C7—C8−2.1 (6)C45—C46—C47—C48−1.6 (6)
C6—C7—C8—C9−177.2 (3)C46—C47—C48—C49−178.4 (3)
C6—C7—C8—C30.8 (5)C46—C47—C48—C430.5 (5)
C4—C3—C8—C71.4 (4)C44—C43—C48—C49179.7 (3)
C2—C3—C8—C7−176.4 (3)C42—C43—C48—C491.1 (4)
C4—C3—C8—C9179.5 (3)C44—C43—C48—C470.8 (4)
C2—C3—C8—C91.7 (4)C42—C43—C48—C47−177.9 (3)
C7—C8—C9—C10175.8 (3)C47—C48—C49—C50177.4 (3)
C3—C8—C9—C10−2.2 (4)C43—C48—C49—C50−1.6 (5)
C8—C9—C10—C10.4 (4)C48—C49—C50—C410.6 (5)
C2—C1—C10—C91.9 (4)C42—C41—C50—C490.8 (5)
C11—C1—C10—C9−174.3 (3)C51—C41—C50—C49−177.0 (3)
C12—N1—C11—C1175.0 (3)C52—N3—C51—C41178.1 (3)
C2—C1—C11—N1−174.5 (3)C42—C41—C51—N3179.9 (3)
C10—C1—C11—N11.7 (5)C50—C41—C51—N3−2.4 (5)
C11—N1—C12—C14−118.7 (4)C51—N3—C52—C54−123.3 (4)
C11—N1—C12—C13119.0 (5)C51—N3—C52—C53116.7 (4)
N1—C12—C14—C15−67.2 (5)N3—C52—C54—C55142.0 (4)
C13—C12—C14—C1551.5 (7)C53—C52—C54—C55−99.5 (6)
N1—C12—C14—C19110.0 (5)N3—C52—C54—C59−40.0 (6)
C13—C12—C14—C19−131.3 (6)C53—C52—C54—C5978.6 (5)
C19—C14—C15—C160.8 (7)C59—C54—C55—C560.3 (7)
C12—C14—C15—C16178.1 (4)C52—C54—C55—C56178.5 (5)
C14—C15—C16—C17−1.1 (8)C54—C55—C56—C57−1.0 (8)
C15—C16—C17—C180.7 (9)C55—C56—C57—C580.9 (8)
C16—C17—C18—C19−0.2 (9)C56—C57—C58—C59−0.2 (8)
C15—C14—C19—C18−0.2 (7)C57—C58—C59—C54−0.5 (8)
C12—C14—C19—C18−177.5 (5)C55—C54—C59—C580.4 (7)
C17—C18—C19—C14−0.1 (9)C52—C54—C59—C58−177.8 (5)
C30—C21—C22—C23−1.3 (4)C70—C61—C62—C63−1.6 (5)
C31—C21—C22—C23177.3 (3)C71—C61—C62—C63174.3 (3)
C21—C22—C23—C280.6 (4)C61—C62—C63—C64−177.3 (3)
C21—C22—C23—C24−178.0 (3)C61—C62—C63—C680.2 (4)
C28—C23—C24—C25−0.5 (5)C68—C63—C64—C65−2.2 (5)
C22—C23—C24—C25178.0 (3)C62—C63—C64—C65175.4 (3)
C23—C24—C25—C26−0.3 (6)C63—C64—C65—C661.1 (6)
C24—C25—C26—C270.8 (6)C64—C65—C66—C671.2 (7)
C25—C26—C27—C28−0.3 (6)C65—C66—C67—C68−2.3 (6)
C24—C23—C28—C29179.4 (3)C64—C63—C68—C69179.2 (3)
C22—C23—C28—C290.8 (4)C62—C63—C68—C691.6 (4)
C24—C23—C28—C271.0 (4)C64—C63—C68—C671.0 (4)
C22—C23—C28—C27−177.6 (3)C62—C63—C68—C67−176.6 (3)
C26—C27—C28—C29−178.9 (3)C66—C67—C68—C69−176.9 (3)
C26—C27—C28—C23−0.6 (5)C66—C67—C68—C631.1 (5)
C23—C28—C29—C30−1.5 (4)C63—C68—C69—C70−1.9 (5)
C27—C28—C29—C30176.9 (3)C67—C68—C69—C70176.2 (3)
C28—C29—C30—C210.7 (5)C68—C69—C70—C610.4 (5)
C22—C21—C30—C290.6 (4)C62—C61—C70—C691.3 (5)
C31—C21—C30—C29−177.9 (3)C71—C61—C70—C69−174.5 (3)
C32—N2—C31—C21179.3 (3)C72—N4—C71—C61178.3 (4)
C22—C21—C31—N2−177.8 (3)C62—C61—C71—N4−172.8 (4)
C30—C21—C31—N20.8 (5)C70—C61—C71—N43.0 (5)
C31—N2—C32—C34−118.9 (4)C71—N4—C72—C73117.8 (5)
C31—N2—C32—C33119.5 (4)C71—N4—C72—C74−118.8 (4)
N2—C32—C34—C39−41.5 (5)N4—C72—C74—C79−64.6 (8)
C33—C32—C34—C3978.3 (4)C73—C72—C74—C7955.6 (9)
N2—C32—C34—C35140.7 (4)N4—C72—C74—C75110.0 (6)
C33—C32—C34—C35−99.5 (5)C73—C72—C74—C75−129.7 (7)
C39—C34—C35—C360.7 (6)C79—C74—C75—C76−1.2 (10)
C32—C34—C35—C36178.5 (4)C72—C74—C75—C76−176.2 (6)
C34—C35—C36—C37−0.6 (8)C74—C75—C76—C77−1.1 (12)
C35—C36—C37—C380.5 (8)C75—C76—C77—C781.6 (14)
C36—C37—C38—C39−0.4 (7)C76—C77—C78—C790.3 (17)
C35—C34—C39—C38−0.6 (5)C75—C74—C79—C783.1 (13)
C32—C34—C39—C38−178.4 (3)C72—C74—C79—C78178.1 (9)
C37—C38—C39—C340.4 (6)C77—C78—C79—C74−2.8 (18)
(2) (S)-(+)-2-({[(4-Methylphenyl)ethyl]imino}methyl)naphthalene top
Crystal data top
C20H19NDx = 1.155 Mg m−3
Mr = 273.36Melting point: 397 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
a = 6.0946 (5) ÅCell parameters from 2035 reflections
b = 7.5732 (5) Åθ = 5.2–68.7°
c = 34.046 (3) ŵ = 0.51 mm−1
V = 1571.4 (2) Å3T = 298 K
Z = 4Prism, colorless
F(000) = 5840.49 × 0.13 × 0.05 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		2770 independent reflections
Radiation source: Enhance (Cu) X-ray Source2048 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 10.5564 pixels mm-1θmax = 66.6°, θmin = 5.2°
ω scansh = −6→7
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −9→9
Tmin = 0.793, Tmax = 0.969l = −40→40
13738 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.0773P]
where P = (Fo2 + 2Fc2)/3
2770 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.09 e Å−3
0 restraintsΔρmin = −0.11 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.9455 (5)0.3422 (3)0.88634 (7)0.0756 (8)
C10.9081 (5)0.4073 (3)0.95510 (8)0.0555 (7)
C21.0099 (5)0.4065 (3)0.99087 (8)0.0548 (7)
H2A1.14620.35240.99330.066*
C30.9129 (5)0.4860 (3)1.02429 (7)0.0533 (7)
C41.0188 (5)0.4938 (4)1.06118 (8)0.0657 (8)
H4A1.15500.44031.06440.079*
C50.9246 (6)0.5786 (4)1.09209 (9)0.0762 (9)
H5A0.99830.58461.11600.091*
C60.7180 (7)0.6567 (4)1.08826 (10)0.0796 (10)
H6A0.65460.71401.10960.095*
C70.6094 (6)0.6492 (4)1.05335 (10)0.0704 (9)
H7A0.47160.70091.05110.084*
C80.7030 (5)0.5642 (3)1.02042 (8)0.0572 (7)
C90.5983 (5)0.5589 (4)0.98321 (9)0.0631 (7)
H9A0.45900.60740.98040.076*
C100.6976 (5)0.4846 (4)0.95165 (8)0.0616 (8)
H10A0.62660.48440.92750.074*
C111.0219 (6)0.3337 (4)0.92099 (8)0.0638 (8)
H11A1.15640.27830.92490.077*
C121.0836 (7)0.2693 (5)0.85469 (9)0.0843 (10)
H12A1.20220.19990.86650.101*
C130.9409 (9)0.1467 (5)0.82976 (11)0.1177 (16)
H13A1.02590.10120.80830.177*
H13B0.81770.21140.81970.177*
H13C0.88940.05050.84570.177*
C141.1828 (6)0.4228 (5)0.83256 (9)0.0739 (9)
C151.3934 (7)0.4772 (6)0.84071 (9)0.0895 (11)
H15A1.47710.41360.85860.107*
C161.4836 (7)0.6251 (7)0.82277 (12)0.1003 (13)
H16A1.62590.65920.82910.120*
C171.3669 (8)0.7220 (6)0.79583 (11)0.0940 (12)
C181.1577 (7)0.6669 (6)0.78760 (10)0.0914 (11)
H18A1.07470.72990.76950.110*
C191.0668 (6)0.5213 (5)0.80540 (9)0.0817 (10)
H19A0.92420.48830.79900.098*
C201.4631 (9)0.8829 (7)0.77589 (13)0.145 (2)
H20A1.61940.88360.77940.218*
H20B1.40150.98770.78730.218*
H20C1.42940.87950.74840.218*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.083 (2)0.0739 (16)0.0700 (15)0.0109 (15)0.0006 (14)0.0041 (12)
C10.0567 (18)0.0421 (14)0.0675 (16)−0.0004 (14)−0.0007 (14)0.0106 (12)
C20.0447 (15)0.0438 (14)0.0759 (17)0.0032 (13)−0.0005 (14)0.0077 (12)
C30.0505 (17)0.0386 (13)0.0709 (16)−0.0027 (13)0.0021 (14)0.0073 (12)
C40.066 (2)0.0528 (15)0.0786 (18)−0.0022 (16)−0.0034 (16)0.0042 (14)
C50.087 (3)0.0661 (19)0.0754 (19)−0.007 (2)−0.0038 (18)−0.0033 (15)
C60.089 (3)0.0602 (19)0.089 (2)−0.0029 (19)0.020 (2)−0.0065 (17)
C70.061 (2)0.0476 (15)0.102 (2)0.0016 (16)0.0172 (19)0.0041 (15)
C80.0521 (18)0.0353 (13)0.0841 (18)−0.0017 (13)0.0042 (15)0.0067 (13)
C90.0454 (17)0.0469 (15)0.097 (2)0.0017 (14)−0.0027 (16)0.0096 (14)
C100.0571 (19)0.0500 (16)0.0776 (18)0.0000 (15)−0.0104 (15)0.0096 (14)
C110.066 (2)0.0494 (15)0.0765 (18)0.0066 (15)−0.0002 (16)0.0064 (13)
C120.095 (3)0.082 (2)0.0757 (19)0.022 (2)0.0023 (19)0.0000 (17)
C130.164 (5)0.088 (3)0.101 (3)−0.014 (3)0.006 (3)−0.019 (2)
C140.071 (2)0.086 (2)0.0640 (17)0.0179 (19)−0.0007 (16)−0.0085 (17)
C150.082 (3)0.114 (3)0.072 (2)0.023 (3)−0.0097 (19)−0.014 (2)
C160.068 (3)0.140 (4)0.093 (3)−0.002 (3)0.006 (2)−0.037 (3)
C170.093 (3)0.104 (3)0.085 (2)−0.011 (3)0.021 (2)−0.014 (2)
C180.093 (3)0.100 (3)0.081 (2)0.006 (2)0.000 (2)0.009 (2)
C190.073 (2)0.091 (2)0.082 (2)0.006 (2)−0.0036 (18)0.0047 (19)
C200.151 (5)0.139 (4)0.145 (4)−0.042 (4)0.042 (4)−0.005 (3)
Geometric parameters (Å, º) top
N1—C111.270 (3)C11—H11A0.9300
N1—C121.475 (4)C12—C141.511 (5)
C1—C21.367 (4)C12—C131.529 (5)
C1—C101.415 (4)C12—H12A0.9800
C1—C111.463 (4)C13—H13A0.9600
C2—C31.416 (3)C13—H13B0.9600
C2—H2A0.9300C13—H13C0.9600
C3—C41.414 (4)C14—C151.376 (5)
C3—C81.416 (4)C14—C191.382 (4)
C4—C51.360 (4)C15—C161.389 (6)
C4—H4A0.9300C15—H15A0.9300
C5—C61.397 (5)C16—C171.373 (6)
C5—H5A0.9300C16—H16A0.9300
C6—C71.361 (4)C17—C181.370 (6)
C6—H6A0.9300C17—C201.513 (6)
C7—C81.413 (4)C18—C191.375 (5)
C7—H7A0.9300C18—H18A0.9300
C8—C91.419 (4)C19—H19A0.9300
C9—C101.355 (4)C20—H20A0.9600
C9—H9A0.9300C20—H20B0.9600
C10—H10A0.9300C20—H20C0.9600
C11—N1—C12116.8 (3)N1—C12—C13108.0 (3)
C2—C1—C10119.2 (3)C14—C12—C13114.7 (3)
C2—C1—C11119.4 (3)N1—C12—H12A108.8
C10—C1—C11121.5 (3)C14—C12—H12A108.8
C1—C2—C3121.6 (3)C13—C12—H12A108.8
C1—C2—H2A119.2C12—C13—H13A109.5
C3—C2—H2A119.2C12—C13—H13B109.5
C4—C3—C8118.5 (3)H13A—C13—H13B109.5
C4—C3—C2122.8 (3)C12—C13—H13C109.5
C8—C3—C2118.7 (3)H13A—C13—H13C109.5
C5—C4—C3121.0 (3)H13B—C13—H13C109.5
C5—C4—H4A119.5C15—C14—C19116.7 (4)
C3—C4—H4A119.5C15—C14—C12120.2 (3)
C4—C5—C6120.5 (3)C19—C14—C12123.0 (3)
C4—C5—H5A119.7C14—C15—C16121.5 (4)
C6—C5—H5A119.7C14—C15—H15A119.3
C7—C6—C5120.1 (3)C16—C15—H15A119.3
C7—C6—H6A119.9C17—C16—C15121.3 (4)
C5—C6—H6A119.9C17—C16—H16A119.4
C6—C7—C8121.0 (3)C15—C16—H16A119.4
C6—C7—H7A119.5C18—C17—C16117.1 (4)
C8—C7—H7A119.5C18—C17—C20120.9 (5)
C7—C8—C3118.8 (3)C16—C17—C20121.9 (5)
C7—C8—C9122.7 (3)C17—C18—C19121.9 (4)
C3—C8—C9118.5 (3)C17—C18—H18A119.0
C10—C9—C8121.2 (3)C19—C18—H18A119.0
C10—C9—H9A119.4C18—C19—C14121.5 (4)
C8—C9—H9A119.4C18—C19—H19A119.3
C9—C10—C1120.7 (3)C14—C19—H19A119.3
C9—C10—H10A119.6C17—C20—H20A109.5
C1—C10—H10A119.6C17—C20—H20B109.5
N1—C11—C1123.0 (3)H20A—C20—H20B109.5
N1—C11—H11A118.5C17—C20—H20C109.5
C1—C11—H11A118.5H20A—C20—H20C109.5
N1—C12—C14107.7 (3)H20B—C20—H20C109.5
C10—C1—C2—C3−2.0 (4)C12—N1—C11—C1177.3 (3)
C11—C1—C2—C3175.9 (2)C2—C1—C11—N1−174.3 (3)
C1—C2—C3—C4−177.1 (3)C10—C1—C11—N13.6 (4)
C1—C2—C3—C81.5 (4)C11—N1—C12—C14−104.8 (3)
C8—C3—C4—C5−1.7 (4)C11—N1—C12—C13130.8 (3)
C2—C3—C4—C5176.9 (3)N1—C12—C14—C1598.3 (4)
C3—C4—C5—C61.4 (5)C13—C12—C14—C15−141.5 (4)
C4—C5—C6—C7−0.3 (5)N1—C12—C14—C19−77.7 (4)
C5—C6—C7—C8−0.5 (5)C13—C12—C14—C1942.5 (5)
C6—C7—C8—C30.1 (4)C19—C14—C15—C160.7 (5)
C6—C7—C8—C9−177.8 (3)C12—C14—C15—C16−175.6 (3)
C4—C3—C8—C71.0 (4)C14—C15—C16—C17−0.7 (5)
C2—C3—C8—C7−177.7 (2)C15—C16—C17—C180.3 (5)
C4—C3—C8—C9178.9 (2)C15—C16—C17—C20−179.7 (4)
C2—C3—C8—C90.3 (4)C16—C17—C18—C190.1 (6)
C7—C8—C9—C10176.4 (3)C20—C17—C18—C19−179.9 (4)
C3—C8—C9—C10−1.5 (4)C17—C18—C19—C140.0 (6)
C8—C9—C10—C11.0 (4)C15—C14—C19—C18−0.3 (5)
C2—C1—C10—C90.7 (4)C12—C14—C19—C18175.9 (3)
C11—C1—C10—C9−177.1 (3)
(3) (R)-(–)-2-({[(4-Methoxylphenyl)ethyl]imino}methyl)naphthalene top
Crystal data top
C20H19NODx = 1.190 Mg m−3
Mr = 289.36Melting point: 384 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
a = 6.1094 (5) ÅCell parameters from 1762 reflections
b = 7.7266 (7) Åθ = 5.2–52.1°
c = 34.225 (4) ŵ = 0.57 mm−1
V = 1615.6 (3) Å3T = 298 K
Z = 4Block, colorless
F(000) = 6160.39 × 0.25 × 0.23 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		3223 independent reflections
Radiation source: Enhance (Cu) X-ray Source1652 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scansθmax = 74.3°, θmin = 5.2°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)		h = −7→7
Tmin = 0.777, Tmax = 1.000k = −9→9
14921 measured reflectionsl = −39→41
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
3223 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1−0.0201 (6)0.5080 (5)0.13755 (13)0.0761 (12)
O1−0.4133 (6)1.0450 (6)0.02034 (10)0.0962 (12)
C10.0868 (7)0.5184 (6)0.20532 (14)0.0630 (12)
C20.0378 (8)0.4754 (6)0.24308 (14)0.0651 (12)
H2A−0.09530.42160.24820.078*
C30.1798 (7)0.5088 (6)0.27452 (15)0.0629 (12)
C40.1334 (8)0.4602 (7)0.31300 (16)0.0750 (14)
H4A0.00060.40680.31860.090*
C50.2790 (10)0.4894 (8)0.34246 (17)0.0886 (16)
H5A0.24570.45390.36770.106*
C60.4796 (10)0.5729 (8)0.33493 (18)0.0903 (17)
H6A0.57820.59350.35510.108*
C70.5273 (8)0.6233 (6)0.29766 (18)0.0797 (15)
H7A0.65980.67850.29280.096*
C80.3836 (7)0.5947 (6)0.26640 (17)0.0661 (13)
C90.4302 (8)0.6393 (6)0.22713 (16)0.0721 (14)
H9A0.56170.69440.22140.086*
C100.2901 (8)0.6045 (7)0.19785 (16)0.0735 (14)
H10A0.32570.63670.17240.088*
C11−0.0607 (8)0.4759 (7)0.17332 (15)0.0732 (14)
H11A−0.19260.42210.17940.088*
C12−0.1820 (8)0.4500 (8)0.10844 (16)0.0832 (15)
H12A−0.30960.40240.12210.100*
C13−0.0727 (11)0.3053 (7)0.08438 (16)0.108 (2)
H13A−0.17240.26550.06460.163*
H13B−0.03520.21070.10130.163*
H13C0.05740.34930.07220.163*
C14−0.2531 (9)0.6019 (8)0.08414 (15)0.0776 (15)
C15−0.1076 (9)0.6836 (8)0.05893 (16)0.0901 (17)
H15A0.03260.63860.05600.108*
C16−0.1656 (8)0.8295 (8)0.03809 (18)0.0862 (16)
H16A−0.06440.88200.02160.103*
C17−0.3741 (9)0.8978 (8)0.04169 (16)0.0814 (15)
C18−0.5227 (9)0.8167 (8)0.06551 (15)0.0879 (17)
H18A−0.66420.85990.06780.105*
C19−0.4615 (9)0.6698 (8)0.08625 (15)0.0836 (16)
H19A−0.56450.61550.10210.100*
C20−0.6143 (10)1.1351 (9)0.0268 (2)0.132 (3)
H20A−0.61201.24290.01290.198*
H20B−0.63161.15710.05430.198*
H20C−0.73421.06570.01770.198*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.074 (3)0.074 (3)0.080 (3)−0.001 (2)0.002 (2)−0.001 (2)
O10.085 (3)0.095 (3)0.108 (3)0.001 (2)−0.004 (2)0.012 (2)
C10.057 (3)0.053 (3)0.080 (3)0.006 (3)0.005 (3)−0.003 (3)
C20.054 (3)0.057 (3)0.085 (3)0.005 (2)0.008 (3)0.000 (3)
C30.060 (3)0.051 (3)0.078 (3)0.007 (2)0.001 (3)−0.004 (3)
C40.071 (3)0.066 (3)0.088 (4)0.004 (3)0.000 (3)0.002 (3)
C50.099 (4)0.076 (4)0.091 (4)0.017 (4)−0.001 (3)−0.001 (3)
C60.086 (4)0.087 (4)0.097 (5)0.009 (4)−0.018 (4)−0.008 (3)
C70.065 (3)0.065 (3)0.109 (4)0.007 (3)−0.008 (4)−0.007 (3)
C80.053 (3)0.050 (3)0.096 (4)0.006 (2)−0.002 (3)−0.003 (3)
C90.058 (3)0.056 (3)0.102 (4)0.001 (3)0.009 (3)0.002 (3)
C100.070 (3)0.064 (3)0.086 (4)0.003 (3)0.008 (3)0.006 (3)
C110.061 (3)0.066 (3)0.092 (4)0.005 (3)0.002 (3)−0.006 (3)
C120.080 (3)0.086 (4)0.084 (4)−0.015 (3)0.000 (3)−0.004 (3)
C130.143 (6)0.074 (4)0.108 (4)0.002 (5)−0.003 (4)−0.010 (3)
C140.073 (3)0.084 (4)0.076 (4)−0.014 (3)−0.001 (3)−0.005 (3)
C150.067 (3)0.084 (4)0.119 (5)0.000 (3)0.010 (3)0.007 (4)
C160.065 (3)0.076 (4)0.117 (5)−0.010 (3)0.019 (3)0.003 (3)
C170.074 (3)0.093 (4)0.078 (4)−0.011 (3)−0.008 (3)−0.004 (3)
C180.061 (3)0.114 (5)0.088 (4)−0.005 (3)−0.002 (3)0.003 (4)
C190.068 (3)0.106 (5)0.076 (4)−0.014 (3)0.004 (3)0.005 (3)
C200.093 (5)0.142 (7)0.161 (7)0.034 (5)−0.002 (4)0.029 (5)
Geometric parameters (Å, º) top
N1—C111.273 (5)C10—H10A0.9300
N1—C121.474 (6)C11—H11A0.9300
O1—C171.373 (6)C12—C141.503 (7)
O1—C201.429 (6)C12—C131.541 (7)
C1—C21.367 (6)C12—H12A0.9800
C1—C101.432 (6)C13—H13A0.9600
C1—C111.456 (6)C13—H13B0.9600
C2—C31.406 (6)C13—H13C0.9600
C2—H2A0.9300C14—C191.379 (7)
C3—C41.399 (6)C14—C151.390 (7)
C3—C81.438 (6)C15—C161.380 (7)
C4—C51.364 (7)C15—H15A0.9300
C4—H4A0.9300C16—C171.385 (7)
C5—C61.408 (8)C16—H16A0.9300
C5—H5A0.9300C17—C181.372 (7)
C6—C71.365 (6)C18—C191.390 (7)
C6—H6A0.9300C18—H18A0.9300
C7—C81.401 (6)C19—H19A0.9300
C7—H7A0.9300C20—H20A0.9600
C8—C91.416 (6)C20—H20B0.9600
C9—C101.345 (6)C20—H20C0.9600
C9—H9A0.9300
C11—N1—C12117.4 (4)N1—C12—C13106.9 (5)
C17—O1—C20118.1 (5)C14—C12—C13113.4 (4)
C2—C1—C10118.1 (5)N1—C12—H12A109.0
C2—C1—C11121.4 (4)C14—C12—H12A109.0
C10—C1—C11120.5 (5)C13—C12—H12A109.0
C1—C2—C3122.9 (4)C12—C13—H13A109.5
C1—C2—H2A118.5C12—C13—H13B109.5
C3—C2—H2A118.5H13A—C13—H13B109.5
C4—C3—C2123.1 (4)C12—C13—H13C109.5
C4—C3—C8118.8 (5)H13A—C13—H13C109.5
C2—C3—C8118.1 (4)H13B—C13—H13C109.5
C5—C4—C3121.3 (5)C19—C14—C15116.8 (5)
C5—C4—H4A119.4C19—C14—C12122.3 (5)
C3—C4—H4A119.4C15—C14—C12120.9 (5)
C4—C5—C6120.6 (6)C16—C15—C14121.8 (5)
C4—C5—H5A119.7C16—C15—H15A119.1
C6—C5—H5A119.7C14—C15—H15A119.1
C7—C6—C5119.2 (5)C15—C16—C17120.1 (5)
C7—C6—H6A120.4C15—C16—H16A120.0
C5—C6—H6A120.4C17—C16—H16A120.0
C6—C7—C8122.3 (5)C18—C17—O1125.4 (5)
C6—C7—H7A118.8C18—C17—C16119.2 (6)
C8—C7—H7A118.8O1—C17—C16115.4 (5)
C7—C8—C9124.1 (5)C17—C18—C19119.9 (5)
C7—C8—C3117.9 (5)C17—C18—H18A120.1
C9—C8—C3118.0 (5)C19—C18—H18A120.1
C10—C9—C8122.0 (5)C14—C19—C18122.2 (5)
C10—C9—H9A119.0C14—C19—H19A118.9
C8—C9—H9A119.0C18—C19—H19A118.9
C9—C10—C1120.8 (5)O1—C20—H20A109.5
C9—C10—H10A119.6O1—C20—H20B109.5
C1—C10—H10A119.6H20A—C20—H20B109.5
N1—C11—C1124.0 (5)O1—C20—H20C109.5
N1—C11—H11A118.0H20A—C20—H20C109.5
C1—C11—H11A118.0H20B—C20—H20C109.5
N1—C12—C14109.3 (5)
C10—C1—C2—C3−1.3 (6)C2—C1—C11—N1−177.7 (4)
C11—C1—C2—C3177.7 (4)C10—C1—C11—N11.3 (7)
C1—C2—C3—C4−177.9 (4)C11—N1—C12—C14124.6 (5)
C1—C2—C3—C81.1 (6)C11—N1—C12—C13−112.3 (5)
C2—C3—C4—C5177.6 (5)N1—C12—C14—C19−111.5 (5)
C8—C3—C4—C5−1.4 (7)C13—C12—C14—C19129.3 (6)
C3—C4—C5—C61.2 (8)N1—C12—C14—C1567.0 (6)
C4—C5—C6—C7−0.5 (8)C13—C12—C14—C15−52.2 (7)
C5—C6—C7—C8−0.1 (8)C19—C14—C15—C162.4 (8)
C6—C7—C8—C9−177.7 (5)C12—C14—C15—C16−176.1 (5)
C6—C7—C8—C3−0.1 (7)C14—C15—C16—C17−0.6 (9)
C4—C3—C8—C70.8 (6)C20—O1—C17—C188.5 (8)
C2—C3—C8—C7−178.2 (4)C20—O1—C17—C16−171.6 (5)
C4—C3—C8—C9178.5 (4)C15—C16—C17—C18−1.3 (8)
C2—C3—C8—C9−0.5 (6)C15—C16—C17—O1178.7 (5)
C7—C8—C9—C10177.8 (5)O1—C17—C18—C19−178.8 (5)
C3—C8—C9—C100.3 (6)C16—C17—C18—C191.3 (8)
C8—C9—C10—C1−0.6 (7)C15—C14—C19—C18−2.5 (8)
C2—C1—C10—C91.1 (7)C12—C14—C19—C18176.0 (5)
C11—C1—C10—C9−177.9 (4)C17—C18—C19—C140.7 (8)
C12—N1—C11—C1177.4 (4)
(4) (R)-(–)-2-({[(4-Fluorophenyl)ethyl]imino}methyl)naphthalene top
Crystal data top
C19H16FNDx = 1.226 Mg m−3
Mr = 277.33Melting point: 395 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.5950 (11) ÅCell parameters from 1285 reflections
b = 5.8997 (9) Åθ = 3.3–22.0°
c = 16.996 (3) ŵ = 0.08 mm−1
β = 99.420 (15)°T = 298 K
V = 751.3 (2) Å3Prism, colorless
Z = 20.74 × 0.21 × 0.09 mm
F(000) = 292
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		2627 independent reflections
Radiation source: Enhance (Mo) X-ray Source1640 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 10.5564 pixels mm-1θmax = 25.0°, θmin = 3.2°
ω scansh = −9→9
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −7→6
Tmin = 0.970, Tmax = 0.994l = −20→20
7823 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.25 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
2627 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.23 e Å−3
1 restraintΔρmin = −0.19 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.0966 (5)0.5690 (9)0.4846 (2)0.1060 (14)
N10.7143 (6)0.6311 (8)0.7811 (3)0.0578 (12)
C10.7641 (6)0.6386 (9)0.9244 (3)0.0446 (13)
C20.8265 (6)0.5262 (9)0.9935 (3)0.0468 (12)
H2A0.88320.38740.99070.056*
C30.8080 (6)0.6138 (8)1.0693 (3)0.0442 (12)
C40.8659 (7)0.4961 (10)1.1407 (3)0.0592 (15)
H4A0.92600.35921.13950.071*
C50.8346 (8)0.5810 (12)1.2119 (4)0.0747 (18)
H5A0.87230.50021.25860.090*
C60.7465 (8)0.7884 (11)1.2153 (4)0.072 (2)
H6A0.72470.84381.26400.086*
C70.6934 (7)0.9077 (10)1.1480 (4)0.0638 (17)
H7A0.63751.04691.15130.077*
C80.7203 (6)0.8270 (9)1.0726 (3)0.0460 (13)
C90.6637 (7)0.9449 (9)1.0009 (4)0.0576 (16)
H9A0.61221.08741.00270.069*
C100.6824 (7)0.8554 (9)0.9292 (3)0.0552 (15)
H10A0.64160.93580.88280.066*
C110.7749 (6)0.5335 (10)0.8471 (3)0.0522 (14)
H11A0.82750.39140.84610.063*
C120.7282 (7)0.5075 (11)0.7078 (3)0.0632 (16)
H12A0.75620.34830.72070.076*
C130.8789 (7)0.6126 (16)0.6692 (4)0.094 (2)
H13A0.88890.53230.62100.142*
H13B0.85220.76890.65700.142*
H13C0.98960.60190.70550.142*
C140.5538 (7)0.5214 (10)0.6512 (3)0.0546 (14)
C150.5010 (9)0.3482 (11)0.5979 (3)0.0685 (17)
H15A0.57080.21820.59960.082*
C160.3472 (9)0.3628 (13)0.5419 (4)0.0777 (19)
H16A0.31350.24500.50630.093*
C170.2474 (8)0.5521 (13)0.5404 (4)0.0712 (17)
C180.2909 (8)0.7271 (12)0.5918 (4)0.0662 (17)
H18A0.21810.85440.58970.079*
C190.4457 (7)0.7122 (10)0.6472 (3)0.0616 (16)
H19A0.47770.83180.68230.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.078 (2)0.141 (4)0.089 (3)−0.014 (3)−0.014 (2)−0.005 (2)
N10.058 (3)0.062 (3)0.053 (3)0.000 (2)0.005 (2)0.001 (3)
C10.037 (3)0.043 (3)0.052 (3)−0.002 (3)0.004 (2)0.000 (3)
C20.043 (3)0.038 (3)0.061 (4)0.004 (2)0.011 (2)0.002 (3)
C30.039 (3)0.041 (3)0.054 (3)−0.001 (3)0.011 (2)−0.001 (3)
C40.064 (3)0.056 (4)0.060 (4)0.008 (3)0.020 (3)0.009 (3)
C50.078 (4)0.092 (5)0.057 (4)0.011 (4)0.017 (3)0.006 (4)
C60.074 (4)0.081 (5)0.064 (4)−0.005 (4)0.022 (4)−0.017 (4)
C70.058 (4)0.056 (4)0.080 (5)0.000 (3)0.018 (3)−0.011 (3)
C80.039 (3)0.042 (3)0.057 (4)−0.004 (3)0.007 (2)−0.003 (3)
C90.053 (3)0.035 (3)0.086 (5)0.004 (3)0.016 (3)−0.003 (3)
C100.054 (3)0.047 (4)0.061 (4)0.003 (3)−0.001 (3)0.006 (3)
C110.048 (3)0.053 (3)0.056 (4)0.005 (3)0.009 (2)−0.002 (3)
C120.065 (4)0.068 (4)0.055 (4)0.008 (3)0.008 (3)0.004 (3)
C130.060 (3)0.154 (7)0.072 (4)−0.001 (5)0.019 (3)0.013 (5)
C140.060 (3)0.059 (4)0.049 (3)−0.001 (3)0.020 (3)0.003 (3)
C150.086 (4)0.062 (4)0.062 (4)0.002 (4)0.026 (4)−0.009 (3)
C160.089 (5)0.084 (5)0.059 (4)−0.017 (4)0.011 (4)−0.016 (4)
C170.062 (4)0.090 (5)0.060 (4)−0.011 (4)0.005 (3)0.000 (4)
C180.056 (4)0.074 (4)0.069 (4)0.002 (3)0.013 (3)0.009 (4)
C190.065 (4)0.063 (4)0.057 (4)−0.006 (3)0.012 (3)−0.005 (3)
Geometric parameters (Å, º) top
F1—C171.367 (6)C9—H9A0.9300
N1—C111.277 (6)C10—H10A0.9300
N1—C121.462 (7)C11—H11A0.9300
C1—C21.364 (7)C12—C141.507 (7)
C1—C101.430 (7)C12—C131.540 (8)
C1—C111.467 (7)C12—H12A0.9800
C2—C31.417 (7)C13—H13A0.9600
C2—H2A0.9300C13—H13B0.9600
C3—C41.405 (7)C13—H13C0.9600
C3—C81.428 (7)C14—C151.381 (7)
C4—C51.365 (7)C14—C191.389 (7)
C4—H4A0.9300C15—C161.383 (8)
C5—C61.400 (9)C15—H15A0.9300
C5—H5A0.9300C16—C171.348 (9)
C6—C71.347 (8)C16—H16A0.9300
C6—H6A0.9300C17—C181.357 (9)
C7—C81.413 (7)C18—C191.384 (8)
C7—H7A0.9300C18—H18A0.9300
C8—C91.408 (7)C19—H19A0.9300
C9—C101.356 (7)
C11—N1—C12117.2 (5)N1—C11—H11A119.0
C2—C1—C10118.6 (5)C1—C11—H11A119.0
C2—C1—C11120.2 (5)N1—C12—C14109.8 (5)
C10—C1—C11121.2 (5)N1—C12—C13109.0 (5)
C1—C2—C3122.3 (5)C14—C12—C13110.1 (5)
C1—C2—H2A118.9N1—C12—H12A109.3
C3—C2—H2A118.9C14—C12—H12A109.3
C4—C3—C2122.8 (5)C13—C12—H12A109.3
C4—C3—C8118.9 (5)C12—C13—H13A109.5
C2—C3—C8118.2 (5)C12—C13—H13B109.5
C5—C4—C3120.6 (5)H13A—C13—H13B109.5
C5—C4—H4A119.7C12—C13—H13C109.5
C3—C4—H4A119.7H13A—C13—H13C109.5
C4—C5—C6120.7 (6)H13B—C13—H13C109.5
C4—C5—H5A119.7C15—C14—C19117.6 (5)
C6—C5—H5A119.7C15—C14—C12120.6 (6)
C7—C6—C5120.0 (6)C19—C14—C12121.7 (5)
C7—C6—H6A120.0C14—C15—C16121.8 (6)
C5—C6—H6A120.0C14—C15—H15A119.1
C6—C7—C8121.7 (6)C16—C15—H15A119.1
C6—C7—H7A119.1C17—C16—C15118.3 (6)
C8—C7—H7A119.1C17—C16—H16A120.8
C9—C8—C7123.3 (5)C15—C16—H16A120.8
C9—C8—C3118.7 (5)C16—C17—C18122.8 (6)
C7—C8—C3118.0 (5)C16—C17—F1118.6 (7)
C10—C9—C8121.5 (5)C18—C17—F1118.6 (7)
C10—C9—H9A119.2C17—C18—C19118.7 (6)
C8—C9—H9A119.2C17—C18—H18A120.7
C9—C10—C1120.7 (5)C19—C18—H18A120.7
C9—C10—H10A119.7C18—C19—C14120.9 (6)
C1—C10—H10A119.7C18—C19—H19A119.5
N1—C11—C1122.0 (5)C14—C19—H19A119.5
C10—C1—C2—C32.0 (7)C12—N1—C11—C1−178.4 (4)
C11—C1—C2—C3−175.6 (4)C2—C1—C11—N1178.4 (4)
C1—C2—C3—C4177.6 (4)C10—C1—C11—N10.9 (7)
C1—C2—C3—C80.1 (7)C11—N1—C12—C14134.2 (5)
C2—C3—C4—C5−175.7 (5)C11—N1—C12—C13−105.2 (6)
C8—C3—C4—C51.7 (7)N1—C12—C14—C15−150.1 (5)
C3—C4—C5—C6−0.9 (9)C13—C12—C14—C1590.0 (7)
C4—C5—C6—C7−0.8 (9)N1—C12—C14—C1933.7 (7)
C5—C6—C7—C81.5 (9)C13—C12—C14—C19−86.2 (7)
C6—C7—C8—C9178.8 (5)C19—C14—C15—C160.4 (8)
C6—C7—C8—C3−0.6 (8)C12—C14—C15—C16−175.9 (5)
C4—C3—C8—C9179.6 (5)C14—C15—C16—C17−0.2 (9)
C2—C3—C8—C9−2.8 (6)C15—C16—C17—C18−0.6 (9)
C4—C3—C8—C7−1.0 (7)C15—C16—C17—F1179.1 (5)
C2—C3—C8—C7176.6 (5)C16—C17—C18—C191.0 (9)
C7—C8—C9—C10−176.0 (5)F1—C17—C18—C19−178.6 (5)
C3—C8—C9—C103.4 (7)C17—C18—C19—C14−0.8 (8)
C8—C9—C10—C1−1.3 (8)C15—C14—C19—C180.1 (8)
C2—C1—C10—C9−1.5 (7)C12—C14—C19—C18176.3 (5)
C11—C1—C10—C9176.1 (5)
(5) (S)-(+)-2-({[(4-Chlorophenyl)ethyl]imino}methyl)naphthalene top
Crystal data top
C19H16ClNDx = 1.250 Mg m−3
Mr = 293.78Melting point: 400 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 6.0567 (5) ÅCell parameters from 3689 reflections
b = 7.6139 (5) Åθ = 3.6–22.5°
c = 33.853 (3) ŵ = 0.24 mm−1
V = 1561.1 (2) Å3T = 298 K
Z = 4Prism, colorless
F(000) = 6160.38 × 0.32 × 0.14 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		2752 independent reflections
Radiation source: Enhance (Mo) X-ray Source2014 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 10.5564 pixels mm-1θmax = 25.0°, θmin = 2.9°
ω scansh = −7→7
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −9→9
Tmin = 0.437, Tmax = 0.703l = −40→40
21167 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.452P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2752 reflectionsΔρmax = 0.18 e Å−3
191 parametersΔρmin = −0.29 e Å−3
0 restraintsAbsolute structure: Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 constraintsAbsolute structure parameter: 0.02 (6)
Primary atom site location: structure-invariant direct methods
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.9465 (4)0.9082 (3)0.27391 (6)0.1435 (8)
N10.4109 (7)0.3451 (5)0.38543 (11)0.0696 (10)
C10.3744 (6)0.4088 (5)0.45465 (12)0.0465 (9)
C20.4749 (6)0.4065 (5)0.49087 (11)0.0460 (9)
H2A0.61130.35150.49340.055*
C30.3788 (6)0.4845 (4)0.52462 (11)0.0443 (9)
C40.4842 (7)0.4899 (5)0.56185 (11)0.0558 (10)
H4A0.62070.43580.56490.067*
C50.3899 (8)0.5727 (6)0.59339 (13)0.0672 (12)
H5A0.46370.57670.61750.081*
C60.1815 (9)0.6517 (6)0.58949 (15)0.0709 (13)
H6A0.11740.70740.61110.085*
C70.0722 (7)0.6473 (5)0.55418 (14)0.0621 (12)
H7A−0.06590.69980.55210.075*
C80.1658 (6)0.5642 (5)0.52077 (12)0.0488 (10)
C90.0627 (7)0.5609 (5)0.48332 (13)0.0558 (11)
H9A−0.07650.61080.48050.067*
C100.1610 (7)0.4874 (5)0.45155 (12)0.0537 (10)
H10A0.08870.48790.42730.064*
C110.4872 (7)0.3361 (5)0.42020 (12)0.0552 (10)
H11A0.62220.28040.42400.066*
C120.5487 (10)0.2724 (7)0.35352 (13)0.0784 (14)
H12A0.66750.20310.36550.094*
C130.4087 (13)0.1510 (7)0.32800 (17)0.111 (2)
H13A0.35800.05380.34360.167*
H13B0.49590.10800.30640.167*
H13C0.28410.21460.31790.167*
C140.6516 (8)0.4269 (7)0.33160 (12)0.0681 (12)
C150.5323 (8)0.5253 (7)0.30452 (13)0.0717 (13)
H15A0.38930.49140.29800.086*
C160.6227 (9)0.6738 (8)0.28686 (15)0.0820 (15)
H16A0.54070.73890.26880.098*
C170.8316 (10)0.7226 (8)0.29619 (16)0.0865 (16)
C180.9557 (9)0.6285 (9)0.32290 (16)0.0914 (18)
H18A1.09830.66370.32930.110*
C190.8638 (9)0.4801 (8)0.34011 (14)0.0829 (15)
H19A0.94760.41490.35790.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1497 (17)0.1490 (17)0.1320 (15)−0.0588 (14)0.0173 (13)0.0114 (12)
N10.082 (3)0.068 (2)0.059 (2)0.013 (2)−0.003 (2)0.0038 (18)
C10.044 (2)0.0332 (18)0.062 (2)−0.0013 (16)−0.0031 (19)0.0092 (17)
C20.0378 (19)0.0349 (18)0.065 (2)0.0024 (17)−0.0001 (19)0.0088 (16)
C30.042 (2)0.0295 (17)0.062 (2)−0.0060 (16)0.0005 (18)0.0073 (17)
C40.054 (2)0.047 (2)0.066 (3)−0.003 (2)−0.002 (2)0.003 (2)
C50.075 (3)0.055 (2)0.071 (3)−0.008 (3)−0.004 (2)−0.003 (2)
C60.085 (4)0.050 (2)0.078 (3)−0.003 (3)0.018 (3)−0.007 (2)
C70.053 (2)0.042 (2)0.091 (3)0.002 (2)0.018 (2)0.005 (2)
C80.043 (2)0.0279 (18)0.076 (3)−0.0029 (17)0.0058 (19)0.0073 (18)
C90.039 (2)0.040 (2)0.088 (3)−0.0001 (19)−0.005 (2)0.010 (2)
C100.052 (2)0.043 (2)0.065 (3)−0.004 (2)−0.011 (2)0.0100 (19)
C110.058 (2)0.044 (2)0.064 (3)0.004 (2)0.002 (2)0.0036 (18)
C120.094 (4)0.078 (3)0.062 (3)0.026 (3)0.000 (3)0.000 (2)
C130.164 (6)0.077 (3)0.093 (4)−0.011 (4)0.006 (4)−0.020 (3)
C140.070 (3)0.079 (3)0.056 (3)0.024 (3)−0.001 (2)−0.011 (2)
C150.065 (3)0.085 (3)0.065 (3)0.003 (3)−0.005 (2)0.001 (3)
C160.082 (4)0.093 (4)0.070 (3)0.004 (3)−0.008 (3)0.006 (3)
C170.083 (4)0.110 (4)0.066 (3)−0.017 (4)0.012 (3)−0.013 (3)
C180.061 (3)0.130 (5)0.083 (4)−0.001 (4)0.000 (3)−0.034 (4)
C190.075 (4)0.110 (4)0.064 (3)0.019 (3)−0.006 (3)−0.014 (3)
Geometric parameters (Å, º) top
Cl1—C171.746 (6)C9—H9A0.9300
N1—C111.266 (5)C10—H10A0.9300
N1—C121.473 (6)C11—H11A0.9300
C1—C21.369 (5)C12—C131.523 (7)
C1—C101.428 (5)C12—C141.524 (7)
C1—C111.461 (5)C12—H12A0.9800
C2—C31.413 (5)C13—H13A0.9600
C2—H2A0.9300C13—H13B0.9600
C3—C41.413 (5)C13—H13C0.9600
C3—C81.432 (5)C14—C191.378 (7)
C4—C51.365 (6)C14—C151.387 (6)
C4—H4A0.9300C15—C161.391 (7)
C5—C61.405 (7)C15—H15A0.9300
C5—H5A0.9300C16—C171.356 (8)
C6—C71.367 (6)C16—H16A0.9300
C6—H6A0.9300C17—C181.377 (8)
C7—C81.415 (5)C18—C191.388 (8)
C7—H7A0.9300C18—H18A0.9300
C8—C91.413 (5)C19—H19A0.9300
C9—C101.351 (5)
C11—N1—C12117.0 (4)N1—C11—H11A118.3
C2—C1—C10118.3 (4)C1—C11—H11A118.3
C2—C1—C11120.1 (3)N1—C12—C13109.2 (5)
C10—C1—C11121.6 (4)N1—C12—C14107.4 (4)
C1—C2—C3122.4 (3)C13—C12—C14114.8 (4)
C1—C2—H2A118.8N1—C12—H12A108.4
C3—C2—H2A118.8C13—C12—H12A108.4
C2—C3—C4123.2 (3)C14—C12—H12A108.4
C2—C3—C8118.4 (3)C12—C13—H13A109.5
C4—C3—C8118.4 (3)C12—C13—H13B109.5
C5—C4—C3121.5 (4)H13A—C13—H13B109.5
C5—C4—H4A119.3C12—C13—H13C109.5
C3—C4—H4A119.3H13A—C13—H13C109.5
C4—C5—C6120.0 (4)H13B—C13—H13C109.5
C4—C5—H5A120.0C19—C14—C15117.7 (5)
C6—C5—H5A120.0C19—C14—C12120.5 (5)
C7—C6—C5120.5 (4)C15—C14—C12121.7 (5)
C7—C6—H6A119.8C14—C15—C16121.2 (5)
C5—C6—H6A119.8C14—C15—H15A119.4
C6—C7—C8121.1 (4)C16—C15—H15A119.4
C6—C7—H7A119.5C17—C16—C15119.3 (5)
C8—C7—H7A119.5C17—C16—H16A120.3
C9—C8—C7123.2 (4)C15—C16—H16A120.3
C9—C8—C3118.2 (4)C16—C17—C18121.3 (6)
C7—C8—C3118.5 (4)C16—C17—Cl1119.5 (5)
C10—C9—C8121.8 (4)C18—C17—Cl1119.2 (5)
C10—C9—H9A119.1C17—C18—C19118.7 (5)
C8—C9—H9A119.1C17—C18—H18A120.6
C9—C10—C1120.9 (4)C19—C18—H18A120.6
C9—C10—H10A119.5C14—C19—C18121.7 (5)
C1—C10—H10A119.5C14—C19—H19A119.1
N1—C11—C1123.4 (4)C18—C19—H19A119.1
C10—C1—C2—C3−2.5 (5)C12—N1—C11—C1177.4 (4)
C11—C1—C2—C3176.0 (3)C2—C1—C11—N1−174.8 (4)
C1—C2—C3—C4−177.3 (3)C10—C1—C11—N13.6 (6)
C1—C2—C3—C81.9 (5)C11—N1—C12—C13130.7 (5)
C2—C3—C4—C5177.4 (4)C11—N1—C12—C14−104.2 (5)
C8—C3—C4—C5−1.8 (5)N1—C12—C14—C1997.9 (5)
C3—C4—C5—C61.4 (6)C13—C12—C14—C19−140.5 (5)
C4—C5—C6—C7−0.4 (6)N1—C12—C14—C15−77.9 (6)
C5—C6—C7—C8−0.3 (6)C13—C12—C14—C1543.8 (6)
C6—C7—C8—C9−177.9 (4)C19—C14—C15—C16−0.7 (7)
C6—C7—C8—C3−0.1 (6)C12—C14—C15—C16175.2 (4)
C2—C3—C8—C9−0.2 (5)C14—C15—C16—C170.3 (8)
C4—C3—C8—C9179.0 (3)C15—C16—C17—C18−0.2 (8)
C2—C3—C8—C7−178.1 (3)C15—C16—C17—Cl1179.7 (4)
C4—C3—C8—C71.1 (5)C16—C17—C18—C190.6 (8)
C7—C8—C9—C10176.9 (4)Cl1—C17—C18—C19−179.3 (4)
C3—C8—C9—C10−0.8 (5)C15—C14—C19—C181.1 (7)
C8—C9—C10—C10.2 (6)C12—C14—C19—C18−174.9 (4)
C2—C1—C10—C91.4 (5)C17—C18—C19—C14−1.0 (8)
C11—C1—C10—C9−177.1 (4)
(6) (S)-(+)-2-({[(4-Bromophenyl)ethyl]imino}methyl)naphthalene top
Crystal data top
C19H16BrNDx = 1.425 Mg m−3
Mr = 338.24Melting point: 415 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 6.0526 (2) ÅCell parameters from 4299 reflections
b = 7.6671 (4) Åθ = 3.2–20.7°
c = 33.9712 (19) ŵ = 2.60 mm−1
V = 1576.46 (13) Å3T = 298 K
Z = 4Block, colorless
F(000) = 6880.36 × 0.22 × 0.19 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		3120 independent reflections
Radiation source: Enhance (Mo) X-ray Source2017 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 10.5564 pixels mm-1θmax = 26.1°, θmin = 2.9°
ω scansh = −7→7
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −9→9
Tmin = 0.876, Tmax = 0.920l = −41→41
19221 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0301P)2 + 0.937P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3120 reflectionsΔρmax = 0.32 e Å−3
191 parametersΔρmin = −0.44 e Å−3
0 restraintsAbsolute structure: Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 constraintsAbsolute structure parameter: −0.009 (6)
Primary atom site location: structure-invariant direct methods
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.95591 (14)0.41300 (11)0.77288 (2)0.1173 (4)
N10.4062 (7)−0.1554 (6)0.88682 (12)0.0624 (12)
C10.3683 (7)−0.0914 (6)0.95548 (13)0.0437 (11)
C20.4704 (7)−0.0932 (6)0.99143 (12)0.0435 (10)
H2A0.6069−0.14790.99380.052*
C30.3747 (7)−0.0144 (5)1.02523 (13)0.0433 (11)
C40.4816 (8)−0.0089 (6)1.06203 (13)0.0533 (12)
H4A0.6188−0.06171.06510.064*
C50.3854 (9)0.0731 (7)1.09306 (16)0.0662 (14)
H5A0.45760.07591.11720.079*
C60.1798 (10)0.1531 (7)1.08916 (18)0.0700 (17)
H6A0.11730.21031.11060.084*
C70.0695 (9)0.1482 (6)1.05408 (16)0.0601 (14)
H7A−0.06860.20051.05190.072*
C80.1636 (7)0.0644 (6)1.02110 (14)0.0438 (11)
C90.0578 (8)0.0608 (6)0.98390 (14)0.0519 (12)
H9A−0.08200.10950.98120.062*
C100.1572 (8)−0.0125 (6)0.95233 (15)0.0509 (12)
H10A0.0858−0.01100.92810.061*
C110.4829 (9)−0.1642 (6)0.92147 (14)0.0529 (12)
H11A0.6179−0.21950.92540.063*
C120.5447 (10)−0.2281 (7)0.85503 (14)0.0682 (15)
H12A0.6637−0.29670.86700.082*
C130.4035 (13)−0.3500 (8)0.82992 (18)0.097 (2)
H13A0.4890−0.39150.80800.145*
H13B0.2767−0.28780.82030.145*
H13C0.3559−0.44720.84560.145*
C140.6470 (8)−0.0754 (8)0.83342 (13)0.0575 (13)
C150.8594 (9)−0.0227 (9)0.84199 (16)0.0704 (16)
H15A0.9426−0.08690.85990.084*
C160.9516 (9)0.1229 (8)0.82467 (16)0.0741 (17)
H16A1.09450.15740.83110.089*
C170.8283 (9)0.2170 (9)0.79764 (15)0.0687 (16)
C180.6181 (9)0.1667 (8)0.78799 (15)0.0699 (16)
H18A0.53640.22990.76970.084*
C190.5288 (9)0.0199 (7)0.80586 (14)0.0633 (14)
H19A0.3866−0.01540.79920.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1195 (6)0.1287 (6)0.1036 (5)−0.0465 (5)0.0041 (5)0.0162 (5)
N10.067 (3)0.066 (3)0.055 (3)0.006 (2)0.004 (2)0.007 (2)
C10.044 (3)0.037 (2)0.050 (3)−0.001 (2)−0.001 (2)0.008 (2)
C20.035 (2)0.035 (2)0.061 (3)−0.002 (2)0.004 (2)0.009 (2)
C30.041 (3)0.033 (2)0.056 (3)−0.005 (2)0.000 (2)0.006 (2)
C40.055 (3)0.050 (3)0.056 (3)−0.004 (2)−0.004 (2)0.003 (2)
C50.078 (4)0.059 (3)0.062 (3)−0.004 (3)0.001 (3)−0.007 (3)
C60.084 (4)0.053 (3)0.073 (4)−0.007 (3)0.023 (3)−0.011 (3)
C70.051 (3)0.044 (3)0.085 (4)0.004 (2)0.017 (3)0.005 (3)
C80.039 (2)0.030 (2)0.063 (3)−0.004 (2)0.001 (2)0.008 (2)
C90.035 (2)0.043 (3)0.078 (3)0.001 (2)−0.001 (3)0.013 (2)
C100.049 (3)0.045 (3)0.059 (3)0.000 (2)−0.013 (2)0.011 (2)
C110.060 (3)0.041 (3)0.057 (3)0.004 (2)−0.001 (3)0.008 (2)
C120.081 (4)0.068 (4)0.056 (3)0.022 (3)0.001 (3)−0.002 (3)
C130.139 (6)0.073 (4)0.079 (4)−0.013 (4)0.003 (4)−0.016 (3)
C140.058 (3)0.073 (3)0.041 (3)0.019 (3)0.000 (2)−0.007 (3)
C150.063 (4)0.095 (5)0.053 (3)0.017 (3)−0.012 (3)−0.012 (3)
C160.052 (3)0.106 (5)0.064 (3)−0.003 (4)0.001 (3)−0.028 (3)
C170.065 (3)0.095 (5)0.046 (3)−0.005 (3)0.005 (3)−0.012 (3)
C180.065 (4)0.089 (4)0.056 (3)0.002 (3)−0.007 (3)0.006 (3)
C190.050 (3)0.080 (4)0.060 (3)0.004 (3)−0.005 (3)0.000 (3)
Geometric parameters (Å, º) top
Br1—C171.887 (6)C9—H9A0.9300
N1—C111.267 (6)C10—H10A0.9300
N1—C121.477 (6)C11—H11A0.9300
C1—C21.369 (6)C12—C141.515 (8)
C1—C101.418 (6)C12—C131.527 (8)
C1—C111.459 (6)C12—H12A0.9800
C2—C31.421 (6)C13—H13A0.9600
C2—H2A0.9300C13—H13B0.9600
C3—C41.408 (6)C13—H13C0.9600
C3—C81.420 (6)C14—C151.379 (7)
C4—C51.358 (7)C14—C191.386 (7)
C4—H4A0.9300C15—C161.380 (8)
C5—C61.393 (8)C15—H15A0.9300
C5—H5A0.9300C16—C171.386 (8)
C6—C71.366 (7)C16—H16A0.9300
C6—H6A0.9300C17—C181.369 (8)
C7—C81.412 (7)C18—C191.388 (8)
C7—H7A0.9300C18—H18A0.9300
C8—C91.417 (6)C19—H19A0.9300
C9—C101.352 (6)
C11—N1—C12116.8 (5)N1—C11—H11A118.6
C2—C1—C10118.6 (4)C1—C11—H11A118.6
C2—C1—C11119.2 (4)N1—C12—C14107.1 (4)
C10—C1—C11122.2 (4)N1—C12—C13108.8 (5)
C1—C2—C3122.2 (4)C14—C12—C13115.5 (5)
C1—C2—H2A118.9N1—C12—H12A108.4
C3—C2—H2A118.9C14—C12—H12A108.4
C4—C3—C8119.2 (4)C13—C12—H12A108.4
C4—C3—C2122.9 (4)C12—C13—H13A109.5
C8—C3—C2117.9 (4)C12—C13—H13B109.5
C5—C4—C3120.4 (5)H13A—C13—H13B109.5
C5—C4—H4A119.8C12—C13—H13C109.5
C3—C4—H4A119.8H13A—C13—H13C109.5
C4—C5—C6120.8 (5)H13B—C13—H13C109.5
C4—C5—H5A119.6C15—C14—C19118.0 (6)
C6—C5—H5A119.6C15—C14—C12120.4 (5)
C7—C6—C5120.5 (5)C19—C14—C12121.6 (5)
C7—C6—H6A119.8C14—C15—C16121.6 (6)
C5—C6—H6A119.8C14—C15—H15A119.2
C6—C7—C8120.5 (5)C16—C15—H15A119.2
C6—C7—H7A119.8C15—C16—C17119.1 (5)
C8—C7—H7A119.8C15—C16—H16A120.5
C7—C8—C9122.3 (4)C17—C16—H16A120.5
C7—C8—C3118.6 (4)C18—C17—C16120.8 (6)
C9—C8—C3119.1 (4)C18—C17—Br1119.9 (5)
C10—C9—C8121.0 (4)C16—C17—Br1119.3 (4)
C10—C9—H9A119.5C17—C18—C19119.1 (6)
C8—C9—H9A119.5C17—C18—H18A120.5
C9—C10—C1121.2 (4)C19—C18—H18A120.5
C9—C10—H10A119.4C14—C19—C18121.4 (5)
C1—C10—H10A119.4C14—C19—H19A119.3
N1—C11—C1122.7 (5)C18—C19—H19A119.3
C10—C1—C2—C3−1.9 (7)C12—N1—C11—C1177.4 (5)
C11—C1—C2—C3175.8 (4)C2—C1—C11—N1−174.6 (5)
C1—C2—C3—C4−177.3 (4)C10—C1—C11—N13.0 (7)
C1—C2—C3—C81.5 (6)C11—N1—C12—C14−104.2 (5)
C8—C3—C4—C5−1.0 (7)C11—N1—C12—C13130.3 (5)
C2—C3—C4—C5177.9 (5)N1—C12—C14—C1598.1 (6)
C3—C4—C5—C60.0 (8)C13—C12—C14—C15−140.6 (6)
C4—C5—C6—C71.0 (8)N1—C12—C14—C19−79.2 (6)
C5—C6—C7—C8−1.0 (8)C13—C12—C14—C1942.1 (7)
C6—C7—C8—C9−178.1 (5)C19—C14—C15—C161.7 (8)
C6—C7—C8—C30.0 (7)C12—C14—C15—C16−175.7 (5)
C4—C3—C8—C70.9 (6)C14—C15—C16—C17−0.8 (8)
C2—C3—C8—C7−178.0 (4)C15—C16—C17—C18−0.2 (8)
C4—C3—C8—C9179.1 (4)C15—C16—C17—Br1−178.5 (4)
C2—C3—C8—C90.2 (6)C16—C17—C18—C190.3 (8)
C7—C8—C9—C10176.5 (5)Br1—C17—C18—C19178.6 (4)
C3—C8—C9—C10−1.7 (7)C15—C14—C19—C18−1.6 (7)
C8—C9—C10—C11.4 (7)C12—C14—C19—C18175.7 (5)
C2—C1—C10—C90.4 (7)C17—C18—C19—C140.6 (8)
C11—C1—C10—C9−177.2 (4)
(7) (S)-(+)-2-({[1-(Naphthalen-1-yl)ethyl]imino}methyl)naphthalene top
Crystal data top
C23H19NDx = 1.200 Mg m−3
Mr = 309.39Melting point: 404 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.8555 (5) ÅCell parameters from 1835 reflections
b = 7.8724 (4) Åθ = 3.6–22.1°
c = 14.0494 (9) ŵ = 0.07 mm−1
β = 99.859 (6)°T = 298 K
V = 856.01 (9) Å3Prism, colorless
Z = 20.45 × 0.35 × 0.11 mm
F(000) = 328
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		3367 independent reflections
Radiation source: Enhance (Mo) X-ray Source2063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 10.5564 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = −9→9
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)		k = −9→9
Tmin = 0.921, Tmax = 1.000l = −17→17
9508 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0473P)2]
where P = (Fo2 + 2Fc2)/3
3367 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.12 e Å−3
1 restraintΔρmin = −0.14 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1−0.1489 (4)0.3645 (4)0.7552 (2)0.0594 (8)
C10.0105 (4)0.3346 (4)0.6238 (2)0.0533 (9)
C20.0180 (5)0.3772 (5)0.5300 (3)0.0600 (9)
H2A−0.07470.43410.49370.072*
C30.1634 (5)0.3367 (4)0.4871 (3)0.0579 (9)
C40.1732 (6)0.3813 (5)0.3899 (3)0.0744 (11)
H4A0.08200.43880.35250.089*
C50.3159 (7)0.3397 (5)0.3515 (3)0.0840 (13)
H5A0.32110.36900.28790.101*
C60.4533 (6)0.2545 (6)0.4061 (4)0.0841 (13)
H6A0.55060.22950.37930.101*
C70.4475 (5)0.2068 (5)0.4987 (3)0.0723 (11)
H7A0.54000.14790.53400.087*
C80.3019 (4)0.2462 (4)0.5417 (3)0.0560 (9)
C90.2885 (5)0.1980 (5)0.6371 (3)0.0644 (10)
H9A0.37660.13460.67320.077*
C100.1488 (5)0.2429 (5)0.6772 (3)0.0601 (10)
H10A0.14470.21250.74080.072*
C11−0.1433 (5)0.3774 (5)0.6659 (3)0.0572 (9)
H11A−0.24130.41590.62480.069*
C12−0.3172 (5)0.4008 (4)0.7839 (3)0.0557 (9)
H12A−0.40470.41690.72590.067*
C13−0.3647 (5)0.2462 (5)0.8398 (3)0.0716 (11)
H13A−0.47680.26300.85680.107*
H13B−0.28070.23200.89750.107*
H13C−0.36650.14660.80020.107*
C14−0.3091 (4)0.5589 (4)0.8471 (2)0.0498 (9)
C15−0.4631 (5)0.6534 (4)0.8513 (3)0.0513 (9)
C16−0.6267 (5)0.6113 (5)0.7974 (3)0.0594 (10)
H16A−0.63710.51550.75810.071*
C17−0.7704 (5)0.7080 (6)0.8015 (3)0.0720 (11)
H17A−0.87620.67740.76510.086*
C18−0.7582 (6)0.8529 (6)0.8604 (3)0.0733 (12)
H18A−0.85540.91940.86220.088*
C19−0.6045 (6)0.8956 (5)0.9146 (3)0.0683 (11)
H19A−0.59810.99060.95440.082*
C20−0.4538 (5)0.7991 (4)0.9120 (3)0.0548 (9)
C21−0.2945 (6)0.8411 (5)0.9699 (3)0.0693 (11)
H21A−0.28800.93351.01170.083*
C22−0.1513 (5)0.7487 (5)0.9655 (3)0.0721 (11)
H22A−0.04730.77861.00410.086*
C23−0.1572 (5)0.6078 (5)0.9034 (3)0.0612 (10)
H23A−0.05660.54710.90050.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0636 (19)0.0600 (19)0.0557 (19)0.0067 (16)0.0132 (15)−0.0052 (16)
C10.055 (2)0.050 (2)0.054 (2)0.0035 (17)0.0075 (18)−0.0057 (17)
C20.066 (2)0.055 (2)0.058 (2)0.011 (2)0.0069 (19)0.0004 (19)
C30.072 (3)0.046 (2)0.057 (2)−0.0050 (19)0.016 (2)−0.0079 (18)
C40.103 (3)0.057 (2)0.067 (3)0.006 (2)0.024 (2)−0.003 (2)
C50.121 (4)0.061 (3)0.080 (3)−0.006 (3)0.045 (3)−0.010 (2)
C60.093 (3)0.070 (3)0.100 (4)−0.008 (3)0.048 (3)−0.024 (3)
C70.066 (3)0.065 (3)0.087 (3)0.001 (2)0.018 (2)−0.019 (2)
C80.059 (2)0.0451 (19)0.064 (2)0.0001 (18)0.0118 (19)−0.0117 (18)
C90.064 (3)0.058 (2)0.068 (3)0.007 (2)0.001 (2)−0.010 (2)
C100.068 (2)0.057 (2)0.054 (2)0.000 (2)0.0061 (19)−0.0075 (19)
C110.059 (2)0.050 (2)0.062 (2)0.0047 (18)0.0078 (19)−0.0023 (19)
C120.060 (2)0.051 (2)0.059 (2)0.0008 (17)0.0151 (18)−0.0023 (18)
C130.085 (3)0.052 (2)0.079 (3)−0.009 (2)0.016 (2)−0.002 (2)
C140.056 (2)0.047 (2)0.048 (2)−0.0038 (17)0.0130 (17)0.0013 (16)
C150.063 (2)0.045 (2)0.050 (2)−0.0091 (17)0.0208 (17)0.0036 (17)
C160.065 (3)0.056 (2)0.061 (2)0.000 (2)0.021 (2)0.0025 (18)
C170.062 (3)0.079 (3)0.077 (3)−0.002 (2)0.019 (2)0.006 (2)
C180.072 (3)0.067 (3)0.088 (3)0.014 (2)0.034 (2)0.009 (3)
C190.086 (3)0.054 (2)0.072 (3)−0.001 (2)0.035 (2)−0.001 (2)
C200.062 (2)0.048 (2)0.057 (2)−0.0079 (18)0.0213 (19)0.0043 (17)
C210.085 (3)0.055 (2)0.072 (3)−0.012 (2)0.024 (2)−0.011 (2)
C220.074 (3)0.067 (3)0.074 (3)−0.020 (2)0.006 (2)−0.010 (2)
C230.063 (2)0.058 (2)0.064 (3)0.000 (2)0.012 (2)0.002 (2)
Geometric parameters (Å, º) top
N1—C111.268 (4)C12—C131.529 (5)
N1—C121.474 (4)C12—H12A0.9800
C1—C21.371 (5)C13—H13A0.9600
C1—C101.409 (5)C13—H13B0.9600
C1—C111.472 (5)C13—H13C0.9600
C2—C31.416 (5)C14—C231.369 (5)
C2—H2A0.9300C14—C151.430 (5)
C3—C81.413 (5)C15—C161.415 (5)
C3—C41.425 (5)C15—C201.424 (4)
C4—C51.365 (6)C16—C171.370 (5)
C4—H4A0.9300C16—H16A0.9300
C5—C61.386 (6)C17—C181.403 (6)
C5—H5A0.9300C17—H17A0.9300
C6—C71.362 (6)C18—C191.355 (5)
C6—H6A0.9300C18—H18A0.9300
C7—C81.417 (5)C19—C201.412 (5)
C7—H7A0.9300C19—H19A0.9300
C8—C91.414 (5)C20—C211.411 (5)
C9—C101.363 (5)C21—C221.350 (5)
C9—H9A0.9300C21—H21A0.9300
C10—H10A0.9300C22—C231.407 (5)
C11—H11A0.9300C22—H22A0.9300
C12—C141.524 (5)C23—H23A0.9300
C11—N1—C12116.1 (3)C14—C12—H12A109.4
C2—C1—C10118.8 (3)C13—C12—H12A109.4
C2—C1—C11120.2 (3)C12—C13—H13A109.5
C10—C1—C11121.0 (3)C12—C13—H13B109.5
C1—C2—C3121.7 (3)H13A—C13—H13B109.5
C1—C2—H2A119.2C12—C13—H13C109.5
C3—C2—H2A119.2H13A—C13—H13C109.5
C8—C3—C2119.0 (3)H13B—C13—H13C109.5
C8—C3—C4118.8 (4)C23—C14—C15119.3 (3)
C2—C3—C4122.2 (4)C23—C14—C12120.8 (3)
C5—C4—C3120.2 (4)C15—C14—C12119.8 (3)
C5—C4—H4A119.9C16—C15—C20117.3 (3)
C3—C4—H4A119.9C16—C15—C14123.6 (3)
C4—C5—C6120.8 (4)C20—C15—C14119.1 (3)
C4—C5—H5A119.6C17—C16—C15121.8 (4)
C6—C5—H5A119.6C17—C16—H16A119.1
C7—C6—C5120.9 (4)C15—C16—H16A119.1
C7—C6—H6A119.6C16—C17—C18120.2 (4)
C5—C6—H6A119.6C16—C17—H17A119.9
C6—C7—C8120.6 (4)C18—C17—H17A119.9
C6—C7—H7A119.7C19—C18—C17119.8 (4)
C8—C7—H7A119.7C19—C18—H18A120.1
C3—C8—C9118.4 (3)C17—C18—H18A120.1
C3—C8—C7118.8 (4)C18—C19—C20121.4 (4)
C9—C8—C7122.8 (4)C18—C19—H19A119.3
C10—C9—C8121.2 (4)C20—C19—H19A119.3
C10—C9—H9A119.4C21—C20—C19121.6 (4)
C8—C9—H9A119.4C21—C20—C15119.0 (3)
C9—C10—C1121.0 (3)C19—C20—C15119.5 (3)
C9—C10—H10A119.5C22—C21—C20120.7 (4)
C1—C10—H10A119.5C22—C21—H21A119.6
N1—C11—C1123.3 (3)C20—C21—H21A119.6
N1—C11—H11A118.3C21—C22—C23120.9 (4)
C1—C11—H11A118.3C21—C22—H22A119.5
N1—C12—C14111.6 (3)C23—C22—H22A119.5
N1—C12—C13107.2 (3)C14—C23—C22120.9 (4)
C14—C12—C13109.9 (3)C14—C23—H23A119.6
N1—C12—H12A109.4C22—C23—H23A119.6
C10—C1—C2—C3−2.3 (5)N1—C12—C14—C23−27.4 (4)
C11—C1—C2—C3−179.5 (3)C13—C12—C14—C2391.3 (4)
C1—C2—C3—C81.7 (5)N1—C12—C14—C15155.4 (3)
C1—C2—C3—C4−179.6 (3)C13—C12—C14—C15−85.9 (4)
C8—C3—C4—C5−1.3 (5)C23—C14—C15—C16−178.8 (3)
C2—C3—C4—C5180.0 (3)C12—C14—C15—C16−1.6 (5)
C3—C4—C5—C6−0.2 (6)C23—C14—C15—C201.7 (5)
C4—C5—C6—C71.5 (6)C12—C14—C15—C20179.0 (3)
C5—C6—C7—C8−1.2 (6)C20—C15—C16—C171.2 (5)
C2—C3—C8—C90.7 (5)C14—C15—C16—C17−178.2 (3)
C4—C3—C8—C9−178.1 (3)C15—C16—C17—C18−0.2 (5)
C2—C3—C8—C7−179.6 (3)C16—C17—C18—C19−1.1 (6)
C4—C3—C8—C71.6 (5)C17—C18—C19—C201.3 (6)
C6—C7—C8—C3−0.4 (5)C18—C19—C20—C21−178.6 (4)
C6—C7—C8—C9179.3 (4)C18—C19—C20—C15−0.2 (5)
C3—C8—C9—C10−2.5 (5)C16—C15—C20—C21177.4 (3)
C7—C8—C9—C10177.9 (4)C14—C15—C20—C21−3.1 (4)
C8—C9—C10—C11.9 (5)C16—C15—C20—C19−1.1 (4)
C2—C1—C10—C90.5 (5)C14—C15—C20—C19178.4 (3)
C11—C1—C10—C9177.7 (3)C19—C20—C21—C22−179.1 (3)
C12—N1—C11—C1−175.7 (3)C15—C20—C21—C222.4 (5)
C2—C1—C11—N1−169.3 (3)C20—C21—C22—C23−0.3 (6)
C10—C1—C11—N113.5 (5)C15—C14—C23—C220.5 (5)
C11—N1—C12—C14−114.4 (3)C12—C14—C23—C22−176.8 (3)
C11—N1—C12—C13125.3 (3)C21—C22—C23—C14−1.2 (6)
(8) (S)-(+)-2-{[(1-Cyclohexylethyl)imino]methyl}naphthalene top
Crystal data top
C19H23NDx = 1.088 Mg m−3
Mr = 265.38Melting point: 356 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 15.406 (3) ÅCell parameters from 2217 reflections
b = 5.9722 (7) Åθ = 3.5–22.2°
c = 36.002 (7) ŵ = 0.06 mm−1
β = 102.058 (18)°T = 298 K
V = 3239.4 (10) Å3Prism, colorless
Z = 80.54 × 0.09 × 0.07 mm
F(000) = 1152
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		10600 independent reflections
Radiation source: Enhance (Mo) X-ray Source3810 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.119
Detector resolution: 10.5564 pixels mm-1θmax = 25.0°, θmin = 2.9°
ω scansh = −18→18
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		k = −7→6
Tmin = 0.995, Tmax = 0.999l = −42→42
19804 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.231 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
10600 reflectionsΔρmax = 0.23 e Å−3
727 parametersΔρmin = −0.18 e Å−3
37 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0043 (8)
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3854 (7)0.2863 (18)0.1115 (3)0.111 (3)
C10.3747 (6)0.3568 (16)0.0448 (3)0.076 (3)
C20.3473 (6)0.5063 (18)0.0164 (4)0.085 (3)
H2A0.32490.64420.02190.102*
C30.3526 (6)0.4535 (15)−0.0220 (3)0.068 (3)
C40.3261 (7)0.6069 (17)−0.0510 (4)0.087 (3)
H4A0.30180.7437−0.04630.105*
C50.3365 (7)0.5529 (19)−0.0873 (4)0.105 (4)
H5A0.31440.6510−0.10710.125*
C60.3805 (7)0.3490 (19)−0.0958 (4)0.102 (4)
H6A0.39350.3208−0.11950.122*
C70.4012 (7)0.2032 (18)−0.0662 (4)0.088 (3)
H7A0.42400.0650−0.07130.105*
C80.3917 (6)0.2399 (16)−0.0296 (4)0.080 (3)
C90.4174 (6)0.0945 (17)0.0017 (4)0.090 (3)
H9A0.4398−0.0459−0.00240.108*
C100.4109 (7)0.1511 (17)0.0375 (4)0.092 (4)
H10A0.43070.05190.05740.110*
C110.3688 (7)0.420 (2)0.0843 (4)0.096 (4)
H11A0.35200.56550.08880.116*
C120.3782 (10)0.371 (3)0.1491 (4)0.132 (5)
H12A0.37470.53480.14760.158*
C130.2921 (11)0.286 (4)0.1584 (4)0.212 (9)
H13A0.27340.38550.17610.318*
H13B0.30160.13900.16940.318*
H13C0.24710.27830.13550.318*
C140.4604 (10)0.309 (3)0.1801 (5)0.169 (7)
H14A0.45260.38270.20350.203*
C150.4727 (13)0.079 (4)0.1887 (7)0.232 (11)
H15A0.4847−0.00020.16680.279*
H15B0.41910.01730.19480.279*
C160.5527 (16)0.047 (4)0.2235 (6)0.253 (12)
H16A0.54250.13230.24510.304*
H16B0.5588−0.10960.23060.304*
C170.6350 (13)0.128 (4)0.2118 (8)0.270 (15)
H17A0.68720.09800.23150.325*
H17B0.64210.05640.18840.325*
C180.6212 (15)0.369 (5)0.2063 (7)0.309 (18)
H18A0.67420.43940.20120.371*
H18B0.60760.43680.22890.371*
C190.5404 (13)0.401 (4)0.1711 (5)0.279 (16)
H19A0.53190.55890.16520.335*
H19B0.55320.32560.14900.335*
N20.2748 (6)0.8298 (13)0.4005 (3)0.086 (3)
C210.3327 (6)0.7862 (15)0.4684 (3)0.065 (2)
C220.3372 (5)0.6515 (14)0.4990 (3)0.064 (2)
H22A0.30700.51580.49610.076*
C230.3858 (6)0.7105 (13)0.5346 (3)0.059 (2)
C240.3952 (6)0.5701 (16)0.5669 (3)0.076 (3)
H24A0.36670.43210.56480.092*
C250.4457 (7)0.6350 (18)0.6011 (3)0.090 (3)
H25A0.45020.54190.62210.108*
C260.4903 (7)0.8380 (19)0.6048 (3)0.098 (4)
H26A0.52430.87960.62830.118*
C270.4848 (7)0.9771 (17)0.5744 (3)0.083 (3)
H27A0.51591.11160.57730.100*
C280.4331 (6)0.9207 (15)0.5388 (3)0.065 (2)
C290.4260 (6)1.0599 (15)0.5063 (3)0.072 (3)
H29A0.45441.19810.50860.086*
C300.3785 (6)0.9945 (15)0.4719 (3)0.069 (3)
H30A0.37601.08520.45070.083*
C310.2838 (6)0.7128 (16)0.4307 (3)0.072 (3)
H31A0.25770.57160.42880.087*
C320.2259 (7)0.7339 (18)0.3644 (3)0.088 (3)
H32A0.20380.58520.36930.105*
C330.1462 (7)0.887 (2)0.3490 (3)0.112 (4)
H33A0.11440.83070.32500.168*
H33B0.16701.03580.34560.168*
H33C0.10750.89070.36670.168*
C340.2894 (7)0.7096 (17)0.3371 (3)0.094 (3)
H34A0.33990.62200.35080.113*
C350.2493 (10)0.574 (2)0.3022 (3)0.127 (5)
H35A0.22760.43260.30990.152*
H35B0.19930.65480.28730.152*
C360.3181 (11)0.530 (3)0.2777 (4)0.153 (6)
H36A0.36520.43650.29180.184*
H36B0.29010.44920.25500.184*
C370.3565 (10)0.740 (3)0.2669 (4)0.140 (5)
H37A0.31050.82580.25040.168*
H37B0.40200.70540.25280.168*
C380.3964 (8)0.880 (2)0.3010 (4)0.125 (4)
H38A0.41591.02260.29280.150*
H38B0.44780.80390.31580.150*
C390.3272 (7)0.9212 (18)0.3261 (3)0.103 (4)
H39A0.35541.00150.34890.123*
H39B0.27971.01420.31230.123*
N30.7594 (6)0.6491 (16)0.3782 (3)0.102 (3)
C410.8088 (6)0.7277 (15)0.4437 (3)0.066 (2)
C420.8160 (5)0.6512 (15)0.4807 (3)0.066 (2)
H42A0.79020.51530.48490.079*
C430.8616 (5)0.7762 (15)0.5118 (3)0.062 (2)
C440.8733 (6)0.6999 (16)0.5498 (3)0.073 (3)
H44A0.84860.56320.55440.088*
C450.9190 (7)0.8190 (18)0.5796 (3)0.083 (3)
H45A0.92590.76370.60420.100*
C460.9567 (7)1.0315 (19)0.5729 (3)0.087 (3)
H46A0.98731.11550.59320.104*
C470.9472 (6)1.1102 (16)0.5363 (3)0.080 (3)
H47A0.97221.24720.53210.096*
C480.9004 (6)0.9874 (15)0.5052 (3)0.065 (2)
C490.8878 (6)1.0654 (14)0.4677 (3)0.072 (3)
H49A0.90931.20610.46310.086*
C500.8448 (6)0.9397 (15)0.4376 (3)0.074 (3)
H50A0.83910.99390.41300.089*
C510.7641 (6)0.5892 (18)0.4119 (3)0.077 (3)
H51A0.73870.45400.41680.093*
C520.7134 (8)0.504 (2)0.3469 (3)0.104 (4)
H52A0.69360.36770.35770.125*
C530.6334 (9)0.625 (3)0.3245 (4)0.183 (8)
H53A0.60890.54000.30210.275*
H53B0.65070.77010.31730.275*
H53C0.58960.64030.33980.275*
C540.7803 (8)0.4390 (19)0.3213 (3)0.090 (3)
H54A0.74640.35960.29920.108*
C550.8201 (12)0.637 (2)0.3071 (4)0.145 (6)
H55A0.85190.72490.32830.174*
H55B0.77390.73010.29230.174*
C560.8848 (15)0.561 (3)0.2820 (4)0.167 (8)
H56A0.85260.47800.26030.201*
H56B0.91160.69070.27270.201*
C570.9570 (11)0.413 (3)0.3052 (5)0.165 (7)
H57A0.99970.37150.29010.198*
H57B0.98810.49330.32750.198*
C580.9152 (9)0.212 (3)0.3168 (4)0.127 (5)
H58A0.96010.11340.33110.152*
H58B0.88400.13200.29450.152*
C590.8498 (7)0.282 (2)0.3414 (3)0.103 (4)
H59A0.82130.14880.34880.124*
H59B0.88230.35260.36430.124*
N40.8847 (6)0.5784 (17)0.1214 (3)0.104 (3)
C610.8680 (6)0.4718 (17)0.0557 (3)0.079 (3)
C620.8375 (6)0.5241 (16)0.0182 (3)0.073 (3)
H62A0.80720.65870.01250.087*
C630.8489 (6)0.3873 (15)−0.0124 (3)0.070 (3)
C640.8195 (7)0.4542 (19)−0.0494 (4)0.092 (3)
H64A0.79050.5905−0.05500.110*
C650.8339 (8)0.315 (2)−0.0779 (4)0.104 (4)
H65A0.81280.3554−0.10320.125*
C660.8806 (8)0.110 (2)−0.0693 (4)0.108 (4)
H66A0.89270.0210−0.08880.130*
C670.9071 (7)0.0467 (19)−0.0331 (4)0.093 (3)
H67A0.9347−0.0915−0.02780.112*
C680.8941 (6)0.1839 (17)−0.0029 (4)0.079 (3)
C690.9230 (7)0.1238 (17)0.0361 (4)0.089 (3)
H69A0.9506−0.01380.04220.106*
C700.9113 (7)0.2626 (17)0.0648 (3)0.084 (3)
H70A0.93150.22090.09000.101*
C710.8551 (7)0.624 (2)0.0865 (4)0.092 (3)
H71A0.82450.75750.08020.110*
C720.8708 (9)0.754 (2)0.1492 (4)0.113 (4)
H72A0.84410.88680.13540.136*
C730.8078 (11)0.656 (3)0.1714 (4)0.163 (6)
H73A0.75310.61770.15440.245*
H73B0.79650.76350.18960.245*
H73C0.83350.52360.18440.245*
C740.9592 (10)0.816 (3)0.1747 (5)0.163 (7)
H74A0.96200.70590.19510.195*
C750.9530 (11)1.028 (3)0.1957 (5)0.179 (7)
H75A0.94531.15240.17800.215*
H75B0.90151.02180.20720.215*
C761.0366 (15)1.065 (5)0.2265 (7)0.305 (18)
H76A1.03091.20380.23970.366*
H76B1.04240.94390.24490.366*
C771.1135 (16)1.074 (3)0.2111 (6)0.253 (12)
H77A1.16511.09930.23130.303*
H77B1.10881.19700.19330.303*
C781.1246 (10)0.855 (3)0.1909 (5)0.192 (8)
H78A1.16880.87440.17550.230*
H78B1.14550.73950.20960.230*
C791.0366 (11)0.782 (4)0.1656 (7)0.316 (18)
H79A1.03360.85290.14110.379*
H79B1.04120.62230.16160.379*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.117 (8)0.117 (8)0.094 (8)−0.004 (7)0.013 (6)−0.004 (7)
C10.055 (6)0.063 (6)0.104 (9)−0.011 (5)0.006 (6)0.011 (6)
C20.057 (6)0.072 (7)0.124 (10)−0.008 (5)0.014 (6)−0.002 (7)
C30.045 (5)0.061 (6)0.093 (8)−0.003 (4)0.000 (5)0.000 (6)
C40.074 (7)0.067 (6)0.110 (9)−0.008 (5)−0.004 (7)0.002 (7)
C50.074 (7)0.074 (8)0.151 (12)−0.004 (6)−0.012 (8)0.014 (8)
C60.100 (9)0.089 (8)0.107 (9)−0.020 (7)−0.002 (7)0.013 (8)
C70.073 (7)0.072 (7)0.113 (10)−0.012 (5)0.010 (7)−0.015 (7)
C80.049 (6)0.068 (7)0.115 (9)−0.004 (5)−0.002 (6)0.014 (7)
C90.058 (6)0.057 (6)0.144 (11)0.009 (5)−0.002 (7)−0.008 (7)
C100.075 (7)0.060 (7)0.123 (10)−0.008 (5)−0.020 (7)0.005 (7)
C110.086 (8)0.092 (8)0.106 (10)−0.011 (6)0.007 (7)−0.014 (8)
C120.134 (13)0.145 (12)0.111 (11)−0.001 (10)0.016 (10)−0.017 (9)
C130.123 (13)0.37 (3)0.156 (14)−0.026 (18)0.053 (11)0.000 (17)
C140.129 (13)0.168 (16)0.190 (17)−0.055 (13)−0.012 (13)0.017 (14)
C150.18 (2)0.184 (19)0.32 (3)−0.024 (16)0.01 (2)0.04 (2)
C160.18 (2)0.32 (3)0.23 (2)0.00 (2)−0.025 (19)0.14 (2)
C170.112 (16)0.25 (3)0.43 (4)0.035 (19)0.01 (2)0.08 (3)
C180.21 (3)0.37 (4)0.29 (3)−0.16 (3)−0.06 (2)0.06 (3)
C190.22 (2)0.40 (4)0.169 (17)−0.19 (2)−0.062 (16)0.13 (2)
N20.094 (6)0.074 (5)0.084 (6)−0.007 (5)0.006 (5)−0.003 (5)
C210.047 (5)0.071 (6)0.078 (7)0.001 (4)0.012 (5)−0.007 (6)
C220.048 (5)0.052 (5)0.091 (7)−0.007 (4)0.013 (5)−0.005 (5)
C230.053 (5)0.046 (5)0.079 (6)−0.002 (4)0.013 (5)0.005 (5)
C240.062 (6)0.066 (6)0.098 (8)−0.003 (5)0.009 (6)0.003 (6)
C250.091 (8)0.086 (7)0.088 (8)−0.011 (6)0.011 (6)0.024 (6)
C260.097 (8)0.106 (9)0.083 (8)−0.026 (7)−0.003 (6)0.004 (7)
C270.072 (7)0.075 (7)0.099 (8)−0.012 (5)0.011 (6)−0.012 (6)
C280.065 (6)0.059 (5)0.071 (6)−0.003 (4)0.010 (5)0.005 (5)
C290.064 (6)0.051 (5)0.101 (8)0.000 (4)0.017 (6)−0.007 (6)
C300.060 (6)0.061 (6)0.092 (7)0.000 (5)0.026 (5)−0.003 (5)
C310.056 (6)0.068 (6)0.094 (8)0.004 (5)0.016 (5)0.004 (6)
C320.085 (7)0.085 (7)0.092 (8)−0.009 (6)0.015 (6)−0.002 (6)
C330.091 (8)0.132 (9)0.108 (9)0.023 (8)0.009 (7)−0.031 (8)
C340.092 (8)0.083 (7)0.099 (8)0.006 (6)−0.003 (7)−0.001 (7)
C350.168 (13)0.100 (9)0.108 (10)−0.009 (9)0.017 (10)−0.006 (8)
C360.192 (17)0.126 (12)0.156 (14)−0.007 (12)0.072 (13)−0.043 (11)
C370.150 (13)0.149 (13)0.127 (12)0.026 (11)0.043 (10)−0.017 (11)
C380.096 (9)0.138 (11)0.151 (12)0.003 (8)0.048 (9)−0.016 (10)
C390.097 (8)0.086 (7)0.129 (10)−0.008 (6)0.032 (8)−0.024 (7)
N30.098 (7)0.114 (8)0.083 (6)0.007 (6)−0.006 (6)−0.021 (6)
C410.048 (5)0.061 (6)0.090 (7)0.011 (4)0.016 (5)−0.005 (5)
C420.049 (5)0.065 (6)0.084 (7)0.006 (4)0.016 (5)0.000 (5)
C430.043 (5)0.066 (6)0.078 (7)0.004 (4)0.017 (5)−0.001 (5)
C440.071 (6)0.062 (6)0.087 (7)−0.004 (5)0.017 (6)−0.010 (6)
C450.082 (7)0.084 (7)0.090 (8)0.001 (6)0.029 (6)0.002 (6)
C460.073 (7)0.099 (8)0.091 (8)−0.004 (6)0.022 (6)−0.010 (7)
C470.061 (6)0.056 (5)0.126 (9)−0.007 (5)0.024 (6)−0.016 (6)
C480.050 (5)0.062 (6)0.084 (7)0.010 (5)0.018 (5)−0.006 (6)
C490.057 (6)0.050 (5)0.113 (8)0.008 (4)0.030 (6)0.008 (6)
C500.069 (7)0.065 (6)0.089 (7)0.005 (5)0.017 (6)0.003 (6)
C510.057 (6)0.097 (7)0.077 (7)−0.003 (5)0.013 (5)−0.004 (7)
C520.098 (9)0.129 (10)0.079 (8)0.006 (8)0.001 (7)−0.009 (7)
C530.101 (10)0.28 (2)0.146 (12)0.083 (13)−0.016 (9)−0.056 (14)
C540.101 (8)0.103 (8)0.066 (7)−0.005 (7)0.013 (6)0.002 (6)
C550.243 (18)0.111 (10)0.082 (9)0.033 (11)0.038 (10)0.017 (8)
C560.30 (3)0.111 (12)0.117 (13)−0.032 (14)0.110 (15)0.004 (10)
C570.144 (15)0.161 (15)0.210 (19)−0.047 (13)0.080 (14)−0.046 (14)
C580.096 (9)0.140 (11)0.154 (12)0.014 (9)0.045 (9)−0.015 (10)
C590.087 (8)0.122 (9)0.099 (8)0.001 (7)0.015 (7)0.000 (7)
N40.097 (7)0.112 (7)0.096 (7)0.008 (6)0.005 (6)0.015 (7)
C610.058 (6)0.079 (7)0.099 (8)0.003 (5)0.014 (6)0.025 (7)
C620.046 (5)0.064 (6)0.107 (8)0.000 (4)0.012 (5)0.020 (6)
C630.058 (6)0.051 (6)0.100 (8)−0.003 (4)0.018 (6)0.003 (6)
C640.091 (8)0.080 (7)0.100 (9)0.009 (6)0.010 (7)0.006 (7)
C650.092 (9)0.105 (9)0.107 (10)0.004 (8)0.001 (7)0.010 (8)
C660.100 (9)0.103 (10)0.118 (11)−0.008 (8)0.019 (8)−0.024 (8)
C670.068 (7)0.080 (7)0.133 (10)0.000 (6)0.024 (7)0.004 (8)
C680.042 (5)0.068 (6)0.126 (10)−0.006 (5)0.016 (6)−0.009 (7)
C690.070 (7)0.064 (7)0.124 (10)0.001 (5)0.001 (7)0.029 (7)
C700.073 (7)0.069 (7)0.103 (8)−0.002 (6)0.003 (6)0.012 (6)
C710.083 (7)0.092 (8)0.100 (9)0.008 (6)0.017 (7)0.013 (7)
C720.096 (9)0.134 (11)0.110 (10)0.028 (8)0.022 (8)0.017 (9)
C730.183 (16)0.186 (15)0.109 (11)0.032 (13)0.003 (11)0.025 (11)
C740.109 (11)0.175 (14)0.186 (15)0.042 (11)−0.012 (11)−0.088 (12)
C750.158 (15)0.180 (15)0.182 (15)0.030 (13)−0.004 (13)−0.082 (13)
C760.21 (3)0.38 (4)0.35 (4)−0.02 (3)0.10 (3)−0.22 (3)
C770.28 (3)0.20 (2)0.27 (3)−0.06 (2)0.05 (2)−0.162 (19)
C780.137 (14)0.215 (19)0.194 (16)0.027 (14)−0.032 (12)−0.079 (15)
C790.112 (14)0.37 (3)0.43 (4)0.029 (19)−0.02 (2)−0.26 (3)
Geometric parameters (Å, º) top
N1—C111.248 (13)N3—C511.255 (11)
N1—C121.472 (15)N3—C521.478 (13)
C1—C21.355 (12)C41—C421.390 (12)
C1—C101.396 (14)C41—C501.417 (13)
C1—C111.493 (14)C41—C511.462 (12)
C2—C31.439 (13)C42—C431.406 (11)
C2—H2A0.9300C42—H42A0.9300
C3—C41.385 (12)C43—C441.418 (12)
C3—C81.460 (13)C43—C481.436 (12)
C4—C51.387 (15)C44—C451.357 (12)
C4—H4A0.9300C44—H44A0.9300
C5—C61.457 (16)C45—C461.436 (14)
C5—H5A0.9300C45—H45A0.9300
C6—C71.360 (14)C46—C471.378 (13)
C6—H6A0.9300C46—H46A0.9300
C7—C81.376 (14)C47—C481.406 (12)
C7—H7A0.9300C47—H47A0.9300
C8—C91.411 (13)C48—C491.403 (12)
C9—C101.355 (14)C49—C501.368 (12)
C9—H9A0.9300C49—H49A0.9300
C10—H10A0.9300C50—H50A0.9300
C11—H11A0.9300C51—H51A0.9300
C12—C131.522 (19)C52—C531.507 (15)
C12—C141.549 (18)C52—C541.567 (15)
C12—H12A0.9800C52—H52A0.9800
C13—H13A0.9600C53—H53A0.9600
C13—H13B0.9600C53—H53B0.9600
C13—H13C0.9600C53—H53C0.9600
C14—C151.411 (17)C54—C551.473 (16)
C14—C191.447 (17)C54—C591.493 (14)
C14—H14A0.9800C54—H54A0.9800
C15—C161.573 (17)C55—C561.55 (2)
C15—H15A0.9700C55—H55A0.9700
C15—H15B0.9700C55—H55B0.9700
C16—C171.50 (2)C56—C571.53 (2)
C16—H16A0.9700C56—H56A0.9700
C16—H16B0.9700C56—H56B0.9700
C17—C181.46 (2)C57—C581.463 (19)
C17—H17A0.9700C57—H57A0.9700
C17—H17B0.9700C57—H57B0.9700
C18—C191.591 (18)C58—C591.531 (15)
C18—H18A0.9700C58—H58A0.9700
C18—H18B0.9700C58—H58B0.9700
C19—H19A0.9700C59—H59A0.9700
C19—H19B0.9700C59—H59B0.9700
N2—C311.273 (11)N4—C711.272 (11)
N2—C321.477 (11)N4—C721.493 (14)
C21—C221.353 (11)C61—C621.369 (12)
C21—C301.423 (12)C61—C701.422 (13)
C21—C311.477 (12)C61—C711.481 (14)
C22—C231.388 (11)C62—C631.413 (12)
C22—H22A0.9300C62—H62A0.9300
C23—C241.416 (11)C63—C641.372 (13)
C23—C281.443 (11)C63—C681.406 (13)
C24—C251.368 (12)C64—C651.376 (14)
C24—H24A0.9300C64—H64A0.9300
C25—C261.386 (13)C65—C661.419 (16)
C25—H25A0.9300C65—H65A0.9300
C26—C271.363 (13)C66—C671.338 (14)
C26—H26A0.9300C66—H66A0.9300
C27—C281.400 (12)C67—C681.410 (14)
C27—H27A0.9300C67—H67A0.9300
C28—C291.422 (12)C68—C691.428 (14)
C29—C301.358 (11)C69—C701.364 (13)
C29—H29A0.9300C69—H69A0.9300
C30—H30A0.9300C70—H70A0.9300
C31—H31A0.9300C71—H71A0.9300
C32—C341.532 (14)C72—C731.499 (18)
C32—C331.538 (13)C72—C741.520 (17)
C32—H32A0.9800C72—H72A0.9800
C33—H33A0.9600C73—H73A0.9600
C33—H33B0.9600C73—H73B0.9600
C33—H33C0.9600C73—H73C0.9600
C34—C391.479 (13)C74—C791.315 (17)
C34—C351.515 (12)C74—C751.488 (15)
C34—H34A0.9800C74—H74A0.9800
C35—C361.535 (15)C75—C761.531 (19)
C35—H35A0.9700C75—H75A0.9700
C35—H35B0.9700C75—H75B0.9700
C36—C371.476 (16)C76—C771.41 (2)
C36—H36A0.9700C76—H76A0.9700
C36—H36B0.9700C76—H76B0.9700
C37—C381.508 (14)C77—C781.521 (17)
C37—H37A0.9700C77—H77A0.9700
C37—H37B0.9700C77—H77B0.9700
C38—C391.554 (13)C78—C791.531 (16)
C38—H38A0.9700C78—H78A0.9700
C38—H38B0.9700C78—H78B0.9700
C39—H39A0.9700C79—H79A0.9700
C39—H39B0.9700C79—H79B0.9700
C11—N1—C12117.3 (12)C51—N3—C52119.5 (10)
C2—C1—C10120.8 (11)C42—C41—C50119.1 (9)
C2—C1—C11118.6 (10)C42—C41—C51119.6 (9)
C10—C1—C11120.5 (10)C50—C41—C51121.4 (10)
C1—C2—C3120.6 (10)C41—C42—C43121.0 (9)
C1—C2—H2A119.7C41—C42—H42A119.5
C3—C2—H2A119.7C43—C42—H42A119.5
C4—C3—C2120.9 (10)C42—C43—C44122.6 (9)
C4—C3—C8120.4 (10)C42—C43—C48119.4 (9)
C2—C3—C8118.6 (9)C44—C43—C48117.9 (9)
C3—C4—C5118.9 (11)C45—C44—C43122.4 (9)
C3—C4—H4A120.6C45—C44—H44A118.8
C5—C4—H4A120.6C43—C44—H44A118.8
C4—C5—C6122.8 (11)C44—C45—C46119.4 (10)
C4—C5—H5A118.6C44—C45—H45A120.3
C6—C5—H5A118.6C46—C45—H45A120.3
C7—C6—C5114.5 (12)C47—C46—C45119.7 (10)
C7—C6—H6A122.7C47—C46—H46A120.1
C5—C6—H6A122.7C45—C46—H46A120.1
C6—C7—C8126.5 (11)C46—C47—C48121.3 (10)
C6—C7—H7A116.8C46—C47—H47A119.4
C8—C7—H7A116.8C48—C47—H47A119.4
C7—C8—C9126.8 (11)C49—C48—C47122.6 (9)
C7—C8—C3116.6 (10)C49—C48—C43118.2 (9)
C9—C8—C3116.6 (11)C47—C48—C43119.2 (9)
C10—C9—C8122.7 (10)C50—C49—C48121.6 (9)
C10—C9—H9A118.6C50—C49—H49A119.2
C8—C9—H9A118.6C48—C49—H49A119.2
C9—C10—C1120.6 (11)C49—C50—C41120.6 (9)
C9—C10—H10A119.7C49—C50—H50A119.7
C1—C10—H10A119.7C41—C50—H50A119.7
N1—C11—C1122.8 (11)N3—C51—C41121.3 (10)
N1—C11—H11A118.6N3—C51—H51A119.4
C1—C11—H11A118.6C41—C51—H51A119.4
N1—C12—C13108.8 (13)N3—C52—C53109.7 (11)
N1—C12—C14112.0 (14)N3—C52—C54108.9 (10)
C13—C12—C14112.3 (14)C53—C52—C54111.6 (10)
N1—C12—H12A107.9N3—C52—H52A108.9
C13—C12—H12A107.9C53—C52—H52A108.9
C14—C12—H12A107.9C54—C52—H52A108.9
C12—C13—H13A109.5C52—C53—H53A109.5
C12—C13—H13B109.5C52—C53—H53B109.5
H13A—C13—H13B109.5H53A—C53—H53B109.5
C12—C13—H13C109.5C52—C53—H53C109.5
H13A—C13—H13C109.5H53A—C53—H53C109.5
H13B—C13—H13C109.5H53B—C53—H53C109.5
C15—C14—C19109.7 (18)C55—C54—C59111.4 (11)
C15—C14—C12116.4 (15)C55—C54—C52112.2 (11)
C19—C14—C12110.7 (15)C59—C54—C52111.5 (9)
C15—C14—H14A106.5C55—C54—H54A107.2
C19—C14—H14A106.5C59—C54—H54A107.2
C12—C14—H14A106.5C52—C54—H54A107.2
C14—C15—C16109.8 (16)C54—C55—C56109.5 (11)
C14—C15—H15A109.7C54—C55—H55A109.8
C16—C15—H15A109.7C56—C55—H55A109.8
C14—C15—H15B109.7C54—C55—H55B109.8
C16—C15—H15B109.7C56—C55—H55B109.8
H15A—C15—H15B108.2H55A—C55—H55B108.2
C17—C16—C15107.8 (16)C57—C56—C55109.6 (12)
C17—C16—H16A110.1C57—C56—H56A109.7
C15—C16—H16A110.1C55—C56—H56A109.7
C17—C16—H16B110.1C57—C56—H56B109.7
C15—C16—H16B110.1C55—C56—H56B109.7
H16A—C16—H16B108.5H56A—C56—H56B108.2
C18—C17—C16104 (2)C58—C57—C56108.4 (13)
C18—C17—H17A110.9C58—C57—H57A110.0
C16—C17—H17A110.9C56—C57—H57A110.0
C18—C17—H17B110.9C58—C57—H57B110.0
C16—C17—H17B110.9C56—C57—H57B110.0
H17A—C17—H17B108.9H57A—C57—H57B108.4
C17—C18—C19107.0 (18)C57—C58—C59108.9 (12)
C17—C18—H18A110.3C57—C58—H58A109.9
C19—C18—H18A110.3C59—C58—H58A109.9
C17—C18—H18B110.3C57—C58—H58B109.9
C19—C18—H18B110.3C59—C58—H58B109.9
H18A—C18—H18B108.6H58A—C58—H58B108.3
C14—C19—C18109.7 (14)C54—C59—C58112.5 (10)
C14—C19—H19A109.7C54—C59—H59A109.1
C18—C19—H19A109.7C58—C59—H59A109.1
C14—C19—H19B109.7C54—C59—H59B109.1
C18—C19—H19B109.7C58—C59—H59B109.1
H19A—C19—H19B108.2H59A—C59—H59B107.8
C31—N2—C32118.8 (8)C71—N4—C72116.0 (10)
C22—C21—C30120.5 (8)C62—C61—C70118.4 (11)
C22—C21—C31120.2 (8)C62—C61—C71121.8 (10)
C30—C21—C31119.2 (9)C70—C61—C71119.8 (10)
C21—C22—C23121.8 (8)C61—C62—C63124.3 (9)
C21—C22—H22A119.1C61—C62—H62A117.8
C23—C22—H22A119.1C63—C62—H62A117.8
C22—C23—C24123.4 (8)C64—C63—C68122.3 (11)
C22—C23—C28118.8 (8)C64—C63—C62121.2 (9)
C24—C23—C28117.8 (8)C68—C63—C62116.4 (10)
C25—C24—C23120.8 (9)C65—C64—C63118.5 (11)
C25—C24—H24A119.6C65—C64—H64A120.8
C23—C24—H24A119.6C63—C64—H64A120.8
C24—C25—C26120.7 (10)C64—C65—C66120.7 (12)
C24—C25—H25A119.6C64—C65—H65A119.6
C26—C25—H25A119.6C66—C65—H65A119.6
C27—C26—C25120.7 (10)C67—C66—C65119.7 (13)
C27—C26—H26A119.7C67—C66—H66A120.2
C25—C26—H26A119.7C65—C66—H66A120.2
C26—C27—C28121.1 (9)C66—C67—C68121.6 (11)
C26—C27—H27A119.5C66—C67—H67A119.2
C28—C27—H27A119.5C68—C67—H67A119.2
C27—C28—C29123.0 (9)C63—C68—C67117.1 (11)
C27—C28—C23118.9 (8)C63—C68—C69119.6 (11)
C29—C28—C23118.1 (8)C67—C68—C69123.2 (10)
C30—C29—C28121.2 (9)C70—C69—C68121.9 (10)
C30—C29—H29A119.4C70—C69—H69A119.1
C28—C29—H29A119.4C68—C69—H69A119.1
C29—C30—C21119.6 (9)C69—C70—C61119.3 (10)
C29—C30—H30A120.2C69—C70—H70A120.3
C21—C30—H30A120.2C61—C70—H70A120.3
N2—C31—C21124.4 (9)N4—C71—C61122.1 (11)
N2—C31—H31A117.8N4—C71—H71A118.9
C21—C31—H31A117.8C61—C71—H71A118.9
N2—C32—C34108.9 (9)N4—C72—C73106.5 (13)
N2—C32—C33108.0 (9)N4—C72—C74109.8 (10)
C34—C32—C33113.2 (9)C73—C72—C74111.7 (13)
N2—C32—H32A108.9N4—C72—H72A109.6
C34—C32—H32A108.9C73—C72—H72A109.6
C33—C32—H32A108.9C74—C72—H72A109.6
C32—C33—H33A109.5C72—C73—H73A109.5
C32—C33—H33B109.5C72—C73—H73B109.5
H33A—C33—H33B109.5H73A—C73—H73B109.5
C32—C33—H33C109.5C72—C73—H73C109.5
H33A—C33—H33C109.5H73A—C73—H73C109.5
H33B—C33—H33C109.5H73B—C73—H73C109.5
C32—C34—C39115.5 (9)C79—C74—C72123.9 (14)
C32—C34—C35112.2 (10)C79—C74—C75114.4 (16)
C39—C34—C35110.5 (9)C72—C74—C75111.7 (13)
C32—C34—H34A106.0C79—C74—H74A100.6
C39—C34—H34A106.0C72—C74—H74A100.6
C35—C34—H34A106.0C75—C74—H74A100.6
C36—C35—C34110.9 (11)C76—C75—C74111.0 (14)
C36—C35—H35A109.5C76—C75—H75A109.4
C34—C35—H35A109.5C74—C75—H75A109.4
C36—C35—H35B109.5C76—C75—H75B109.4
C34—C35—H35B109.5C74—C75—H75B109.4
H35A—C35—H35B108.0H75A—C75—H75B108.0
C37—C36—C35111.6 (11)C77—C76—C75112 (2)
C37—C36—H36A109.3C77—C76—H76A109.3
C35—C36—H36A109.3C75—C76—H76A109.3
C37—C36—H36B109.3C77—C76—H76B109.3
C35—C36—H36B109.3C75—C76—H76B109.3
H36A—C36—H36B108.0H76A—C76—H76B108.0
C36—C37—C38111.9 (12)C76—C77—C78110.1 (18)
C36—C37—H37A109.2C76—C77—H77A109.6
C38—C37—H37A109.2C78—C77—H77A109.6
C36—C37—H37B109.2C76—C77—H77B109.6
C38—C37—H37B109.2C78—C77—H77B109.6
H37A—C37—H37B107.9H77A—C77—H77B108.2
C37—C38—C39110.4 (10)C79—C78—C77110.7 (14)
C37—C38—H38A109.6C79—C78—H78A109.5
C39—C38—H38A109.6C77—C78—H78A109.5
C37—C38—H38B109.6C79—C78—H78B109.5
C39—C38—H38B109.6C77—C78—H78B109.5
H38A—C38—H38B108.1H78A—C78—H78B108.1
C34—C39—C38112.1 (9)C74—C79—C78123.1 (16)
C34—C39—H39A109.2C74—C79—H79A106.6
C38—C39—H39A109.2C78—C79—H79A106.6
C34—C39—H39B109.2C74—C79—H79B106.6
C38—C39—H39B109.2C78—C79—H79B106.6
H39A—C39—H39B107.9H79A—C79—H79B106.5
C10—C1—C2—C31.7 (14)C50—C41—C42—C43−2.9 (12)
C11—C1—C2—C3179.4 (8)C51—C41—C42—C43177.4 (8)
C1—C2—C3—C4−178.8 (9)C41—C42—C43—C44−177.5 (8)
C1—C2—C3—C8−2.7 (13)C41—C42—C43—C480.8 (12)
C2—C3—C4—C5176.8 (9)C42—C43—C44—C45178.6 (9)
C8—C3—C4—C50.7 (14)C48—C43—C44—C450.2 (13)
C3—C4—C5—C6−5.0 (15)C43—C44—C45—C460.6 (15)
C4—C5—C6—C77.5 (15)C44—C45—C46—C47−1.0 (14)
C5—C6—C7—C8−6.2 (16)C45—C46—C47—C480.6 (14)
C6—C7—C8—C9−176.3 (10)C46—C47—C48—C49178.5 (9)
C6—C7—C8—C32.4 (15)C46—C47—C48—C430.2 (13)
C4—C3—C8—C70.7 (13)C42—C43—C48—C492.6 (11)
C2—C3—C8—C7−175.5 (8)C44—C43—C48—C49−179.0 (8)
C4—C3—C8—C9179.5 (8)C42—C43—C48—C47−179.0 (8)
C2—C3—C8—C93.3 (12)C44—C43—C48—C47−0.6 (11)
C7—C8—C9—C10175.4 (10)C47—C48—C49—C50177.7 (8)
C3—C8—C9—C10−3.2 (14)C43—C48—C49—C50−4.1 (12)
C8—C9—C10—C12.3 (16)C48—C49—C50—C412.0 (13)
C2—C1—C10—C9−1.5 (15)C42—C41—C50—C491.5 (12)
C11—C1—C10—C9−179.1 (9)C51—C41—C50—C49−178.8 (8)
C12—N1—C11—C1179.1 (10)C52—N3—C51—C41−179.8 (9)
C2—C1—C11—N1173.7 (11)C42—C41—C51—N3−177.3 (9)
C10—C1—C11—N1−8.6 (16)C50—C41—C51—N33.0 (14)
C11—N1—C12—C13103.3 (16)C51—N3—C52—C53116.4 (13)
C11—N1—C12—C14−131.9 (14)C51—N3—C52—C54−121.2 (11)
N1—C12—C14—C15−66 (2)N3—C52—C54—C55−55.6 (13)
C13—C12—C14—C1556 (3)C53—C52—C54—C5565.7 (14)
N1—C12—C14—C1960 (2)N3—C52—C54—C5970.1 (12)
C13—C12—C14—C19−177.6 (18)C53—C52—C54—C59−168.6 (11)
C19—C14—C15—C1659 (2)C59—C54—C55—C5654.5 (15)
C12—C14—C15—C16−174.1 (16)C52—C54—C55—C56−179.7 (11)
C14—C15—C16—C17−64 (3)C54—C55—C56—C57−59.0 (18)
C15—C16—C17—C1866 (3)C55—C56—C57—C5862.9 (17)
C16—C17—C18—C19−66 (3)C56—C57—C58—C59−61.0 (17)
C15—C14—C19—C18−59 (3)C55—C54—C59—C58−54.8 (13)
C12—C14—C19—C18170.9 (18)C52—C54—C59—C58179.1 (10)
C17—C18—C19—C1464 (3)C57—C58—C59—C5457.9 (15)
C30—C21—C22—C230.3 (13)C70—C61—C62—C63−2.4 (14)
C31—C21—C22—C23177.1 (8)C71—C61—C62—C63179.0 (9)
C21—C22—C23—C24−177.3 (8)C61—C62—C63—C64−177.5 (9)
C21—C22—C23—C28−0.4 (12)C61—C62—C63—C680.7 (13)
C22—C23—C24—C25178.4 (9)C68—C63—C64—C650.9 (15)
C28—C23—C24—C251.6 (14)C62—C63—C64—C65179.0 (10)
C23—C24—C25—C26−1.2 (16)C63—C64—C65—C66−2.0 (17)
C24—C25—C26—C27−0.1 (17)C64—C65—C66—C673.4 (18)
C25—C26—C27—C281.0 (17)C65—C66—C67—C68−3.6 (17)
C26—C27—C28—C29−179.5 (10)C64—C63—C68—C67−1.1 (13)
C26—C27—C28—C23−0.6 (15)C62—C63—C68—C67−179.2 (8)
C22—C23—C28—C27−177.7 (9)C64—C63—C68—C69180.0 (9)
C24—C23—C28—C27−0.7 (13)C62—C63—C68—C691.9 (12)
C22—C23—C28—C291.3 (12)C66—C67—C68—C632.4 (15)
C24—C23—C28—C29178.3 (8)C66—C67—C68—C69−178.7 (10)
C27—C28—C29—C30176.8 (9)C63—C68—C69—C70−2.7 (14)
C23—C28—C29—C30−2.1 (13)C67—C68—C69—C70178.4 (9)
C28—C29—C30—C212.0 (13)C68—C69—C70—C611.0 (15)
C22—C21—C30—C29−1.1 (13)C62—C61—C70—C691.5 (14)
C31—C21—C30—C29−177.9 (8)C71—C61—C70—C69−179.8 (9)
C32—N2—C31—C21178.6 (8)C72—N4—C71—C61176.9 (10)
C22—C21—C31—N2178.8 (9)C62—C61—C71—N4−178.7 (10)
C30—C21—C31—N2−4.4 (13)C70—C61—C71—N42.7 (16)
C31—N2—C32—C34−116.4 (10)C71—N4—C72—C73113.8 (12)
C31—N2—C32—C33120.3 (10)C71—N4—C72—C74−125.0 (14)
N2—C32—C34—C39−62.6 (12)N4—C72—C74—C7922 (3)
C33—C32—C34—C3957.5 (12)C73—C72—C74—C79140 (2)
N2—C32—C34—C35169.6 (9)N4—C72—C74—C75165.1 (14)
C33—C32—C34—C35−70.3 (12)C73—C72—C74—C75−77.0 (19)
C32—C34—C35—C36−173.4 (11)C79—C74—C75—C76−44 (3)
C39—C34—C35—C3656.1 (14)C72—C74—C75—C76169.3 (18)
C34—C35—C36—C37−56.3 (16)C74—C75—C76—C7759 (3)
C35—C36—C37—C3855.6 (17)C75—C76—C77—C78−60 (3)
C36—C37—C38—C39−54.0 (16)C76—C77—C78—C7946 (3)
C32—C34—C39—C38175.5 (9)C72—C74—C79—C78177.2 (19)
C35—C34—C39—C38−55.8 (13)C75—C74—C79—C7835 (4)
C37—C38—C39—C3454.6 (15)C77—C78—C79—C74−35 (4)
(9) (S)-(–)-2-{[(1,2,3,4-Tetrahydronaphthalen-1-yl)imino]methyl}naphthalene top
Crystal data top
C21H19NDx = 1.159 Mg m−3
Mr = 285.37Melting point: 359 K
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
a = 7.7571 (13) ÅCell parameters from 2340 reflections
b = 5.9246 (10) Åθ = 3.4–24.8°
c = 17.820 (4) ŵ = 0.07 mm−1
β = 92.682 (16)°T = 298 K
V = 818.1 (2) Å3Plate, colorless
Z = 20.88 × 0.43 × 0.08 mm
F(000) = 304
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		2884 independent reflections
Radiation source: Enhance (Mo) X-ray Source1822 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ω scansθmax = 25.0°, θmin = 3.4°
Absorption correction: analytical
(CrysAlis PRO; Agilent, 2013)		h = −9→9
Tmin = 0.857, Tmax = 0.983k = −7→7
15266 measured reflectionsl = −21→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.44 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
2884 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.21 e Å−3
1 restraintΔρmin = −0.19 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0570 (5)0.8729 (8)0.2802 (2)0.0759 (12)
C10.1450 (5)0.8980 (8)0.4110 (2)0.0520 (11)
C20.1520 (5)0.7961 (7)0.4795 (2)0.0513 (11)
H2A0.09850.65700.48480.062*
C30.2383 (4)0.8954 (7)0.5428 (2)0.0505 (11)
C40.2520 (5)0.7902 (8)0.6136 (2)0.0623 (12)
H4A0.19810.65190.62030.075*
C50.3425 (6)0.8863 (10)0.6725 (3)0.0746 (14)
H5A0.35300.81190.71840.090*
C60.4205 (6)1.0996 (10)0.6636 (3)0.0736 (14)
H6A0.48121.16600.70410.088*
C70.4077 (5)1.2086 (9)0.5965 (3)0.0659 (13)
H7A0.45911.34930.59160.079*
C80.3169 (5)1.1104 (7)0.5340 (3)0.0512 (11)
C90.3038 (5)1.2154 (8)0.4628 (3)0.0603 (12)
H9A0.35301.35700.45670.072*
C100.2213 (6)1.1146 (7)0.4033 (3)0.0576 (12)
H10A0.21431.18740.35710.069*
C110.0660 (5)0.7838 (8)0.3448 (3)0.0629 (13)
H11A0.02060.63990.35060.075*
C12−0.0153 (7)0.7397 (11)0.2176 (3)0.0856 (16)
H12A−0.05390.59400.23680.103*
C130.1227 (7)0.6994 (13)0.1637 (3)0.0904 (17)
C140.2407 (10)0.5324 (18)0.1776 (4)0.144 (3)
H14A0.23060.43710.21860.173*
C150.3808 (14)0.504 (2)0.1285 (6)0.181 (6)
H15A0.46450.39400.13730.217*
C160.3856 (10)0.641 (3)0.0708 (6)0.172 (6)
H16A0.47490.62170.03830.206*
C170.2684 (12)0.813 (2)0.0543 (4)0.159 (4)
H17A0.28070.90440.01250.191*
C180.1342 (8)0.8459 (16)0.1003 (4)0.116 (2)
C19−0.0029 (12)1.0224 (17)0.0818 (5)0.147 (3)
H19A0.05351.16200.06850.176*
H19B−0.07220.97260.03820.176*
C20−0.1181 (12)1.0682 (18)0.1435 (5)0.142 (3)
H20A−0.05951.16770.17970.170*
H20B−0.22031.14590.12350.170*
C21−0.1706 (8)0.8645 (17)0.1819 (4)0.125 (3)
H21A−0.23140.76570.14620.150*
H21B−0.24930.90420.22050.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.075 (3)0.081 (3)0.073 (3)−0.011 (3)0.006 (2)−0.009 (2)
C10.036 (2)0.048 (3)0.073 (3)0.003 (2)0.0109 (19)0.000 (2)
C20.035 (2)0.037 (3)0.083 (3)−0.0009 (19)0.011 (2)0.000 (2)
C30.0297 (19)0.044 (3)0.078 (3)0.006 (2)0.0121 (19)0.000 (2)
C40.053 (2)0.055 (3)0.080 (3)0.002 (2)0.012 (2)0.007 (2)
C50.061 (3)0.086 (4)0.077 (3)0.011 (3)0.006 (2)0.005 (3)
C60.049 (3)0.088 (4)0.084 (3)0.003 (3)0.000 (2)−0.018 (3)
C70.046 (2)0.056 (3)0.096 (4)0.000 (3)0.008 (2)−0.016 (3)
C80.034 (2)0.037 (3)0.083 (3)0.0043 (19)0.012 (2)−0.007 (2)
C90.044 (2)0.041 (3)0.097 (4)0.000 (2)0.017 (2)−0.007 (3)
C100.049 (2)0.047 (3)0.077 (3)0.004 (2)0.013 (2)0.006 (2)
C110.045 (2)0.059 (3)0.086 (3)−0.004 (2)0.012 (2)−0.009 (3)
C120.085 (4)0.096 (4)0.076 (3)−0.018 (3)0.005 (3)−0.011 (3)
C130.070 (3)0.123 (5)0.079 (4)−0.018 (4)0.001 (3)−0.021 (4)
C140.094 (5)0.217 (10)0.119 (6)0.019 (7)−0.014 (5)−0.054 (6)
C150.122 (8)0.273 (16)0.143 (8)0.033 (9)−0.043 (8)−0.053 (10)
C160.072 (5)0.298 (17)0.145 (8)0.019 (7)0.000 (6)−0.093 (10)
C170.120 (6)0.242 (13)0.117 (6)−0.059 (8)0.031 (5)−0.036 (7)
C180.090 (4)0.170 (7)0.089 (4)−0.026 (5)0.020 (4)−0.044 (5)
C190.157 (7)0.144 (7)0.143 (7)0.001 (7)0.042 (6)0.017 (6)
C200.146 (7)0.152 (8)0.128 (6)0.013 (7)0.004 (6)−0.005 (6)
C210.085 (4)0.160 (8)0.130 (5)0.001 (5)0.003 (4)−0.029 (6)
Geometric parameters (Å, º) top
N1—C111.265 (5)C12—C131.491 (7)
N1—C121.457 (6)C12—C211.527 (9)
C1—C21.360 (6)C12—H12A0.9800
C1—C101.422 (6)C13—C141.363 (9)
C1—C111.469 (6)C13—C181.430 (9)
C2—C31.413 (5)C14—C151.436 (12)
C2—H2A0.9300C14—H14A0.9300
C3—C41.407 (6)C15—C161.312 (14)
C3—C81.424 (6)C15—H15A0.9300
C4—C51.360 (6)C16—C171.386 (15)
C4—H4A0.9300C16—H16A0.9300
C5—C61.413 (8)C17—C181.369 (9)
C5—H5A0.9300C17—H17A0.9300
C6—C71.359 (7)C18—C191.517 (10)
C6—H6A0.9300C19—C201.475 (10)
C7—C81.415 (6)C19—H19A0.9700
C7—H7A0.9300C19—H19B0.9700
C8—C91.412 (6)C20—C211.454 (11)
C9—C101.352 (6)C20—H20A0.9700
C9—H9A0.9300C20—H20B0.9700
C10—H10A0.9300C21—H21A0.9700
C11—H11A0.9300C21—H21B0.9700
C11—N1—C12118.2 (5)C13—C12—H12A108.9
C2—C1—C10119.2 (4)C21—C12—H12A108.9
C2—C1—C11120.9 (4)C14—C13—C18121.2 (7)
C10—C1—C11119.9 (4)C14—C13—C12119.7 (7)
C1—C2—C3121.9 (4)C18—C13—C12119.0 (7)
C1—C2—H2A119.0C13—C14—C15119.6 (9)
C3—C2—H2A119.0C13—C14—H14A120.2
C4—C3—C2123.0 (4)C15—C14—H14A120.2
C4—C3—C8118.7 (4)C16—C15—C14117.2 (11)
C2—C3—C8118.3 (4)C16—C15—H15A121.4
C5—C4—C3121.4 (5)C14—C15—H15A121.4
C5—C4—H4A119.3C15—C16—C17125.2 (11)
C3—C4—H4A119.3C15—C16—H16A117.4
C4—C5—C6119.8 (5)C17—C16—H16A117.4
C4—C5—H5A120.1C18—C17—C16119.2 (10)
C6—C5—H5A120.1C18—C17—H17A120.4
C7—C6—C5120.6 (5)C16—C17—H17A120.4
C7—C6—H6A119.7C17—C18—C13117.6 (9)
C5—C6—H6A119.7C17—C18—C19120.8 (9)
C6—C7—C8120.7 (5)C13—C18—C19121.4 (6)
C6—C7—H7A119.6C20—C19—C18114.0 (7)
C8—C7—H7A119.6C20—C19—H19A108.7
C9—C8—C7122.6 (5)C18—C19—H19A108.7
C9—C8—C3118.6 (4)C20—C19—H19B108.7
C7—C8—C3118.8 (4)C18—C19—H19B108.7
C10—C9—C8121.4 (5)H19A—C19—H19B107.6
C10—C9—H9A119.3C21—C20—C19113.0 (8)
C8—C9—H9A119.3C21—C20—H20A109.0
C9—C10—C1120.5 (4)C19—C20—H20A109.0
C9—C10—H10A119.8C21—C20—H20B109.0
C1—C10—H10A119.8C19—C20—H20B109.0
N1—C11—C1122.8 (5)H20A—C20—H20B107.8
N1—C11—H11A118.6C20—C21—C12111.4 (6)
C1—C11—H11A118.6C20—C21—H21A109.3
N1—C12—C13108.5 (4)C12—C21—H21A109.3
N1—C12—C21109.0 (5)C20—C21—H21B109.3
C13—C12—C21112.6 (5)C12—C21—H21B109.3
N1—C12—H12A108.9H21A—C21—H21B108.0
C10—C1—C2—C3−2.3 (6)C11—N1—C12—C13−115.5 (6)
C11—C1—C2—C3175.3 (3)C11—N1—C12—C21121.6 (6)
C1—C2—C3—C4−177.9 (4)N1—C12—C13—C1480.6 (7)
C1—C2—C3—C81.1 (5)C21—C12—C13—C14−158.7 (6)
C2—C3—C4—C5177.1 (4)N1—C12—C13—C18−95.9 (6)
C8—C3—C4—C5−2.0 (6)C21—C12—C13—C1824.9 (8)
C3—C4—C5—C62.0 (6)C18—C13—C14—C150.9 (10)
C4—C5—C6—C7−0.8 (7)C12—C13—C14—C15−175.5 (7)
C5—C6—C7—C8−0.4 (7)C13—C14—C15—C16−1.4 (13)
C6—C7—C8—C9−178.5 (4)C14—C15—C16—C171.3 (16)
C6—C7—C8—C30.3 (6)C15—C16—C17—C18−0.6 (15)
C4—C3—C8—C9179.7 (4)C16—C17—C18—C130.0 (11)
C2—C3—C8—C90.6 (5)C16—C17—C18—C19−176.3 (7)
C4—C3—C8—C70.8 (5)C14—C13—C18—C17−0.2 (9)
C2—C3—C8—C7−178.3 (4)C12—C13—C18—C17176.2 (6)
C7—C8—C9—C10177.7 (4)C14—C13—C18—C19176.1 (6)
C3—C8—C9—C10−1.1 (6)C12—C13—C18—C19−7.5 (8)
C8—C9—C10—C1−0.1 (6)C17—C18—C19—C20−168.6 (7)
C2—C1—C10—C91.8 (6)C13—C18—C19—C2015.2 (10)
C11—C1—C10—C9−175.9 (4)C18—C19—C20—C21−42.0 (10)
C12—N1—C11—C1176.6 (4)C19—C20—C21—C1261.1 (9)
C2—C1—C11—N1−180.0 (4)N1—C12—C21—C2069.0 (7)
C10—C1—C11—N1−2.3 (6)C13—C12—C21—C20−51.5 (8)
(10) (+)-2-({[(1S,2S,3S,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl]imino}methyl}naphthalene top
Crystal data top
C21H25NDx = 1.142 Mg m−3
Mr = 291.42Melting point: 373 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
a = 6.32427 (18) ÅCell parameters from 4989 reflections
b = 14.4559 (3) Åθ = 3.9–73.9°
c = 18.5421 (5) ŵ = 0.49 mm−1
V = 1695.17 (8) Å3T = 150 K
Z = 4Prism, colorless
F(000) = 6320.40 × 0.15 × 0.12 mm
Data collection top
Agilent Xcalibur Atlas Gemini
diffractometer		3417 independent reflections
Radiation source: Enhance (Cu) X-ray Source2913 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 10.5564 pixels mm-1θmax = 74.1°, θmin = 3.9°
ω scansh = −7→7
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)		k = −18→17
Tmin = 0.976, Tmax = 1.000l = −23→22
19648 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.2349P]
where P = (Fo2 + 2Fc2)/3
3417 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1655 (3)0.02849 (13)0.12338 (10)0.0287 (4)
C10.1959 (4)0.19008 (16)0.09368 (12)0.0275 (5)
C20.0953 (4)0.26587 (16)0.06545 (12)0.0278 (5)
H2A−0.04180.25900.04520.033*
C30.1928 (4)0.35464 (16)0.06593 (12)0.0283 (5)
C40.0890 (5)0.43469 (17)0.03906 (13)0.0347 (6)
H4A−0.04780.42940.01840.042*
C50.1852 (5)0.51971 (18)0.04284 (14)0.0408 (7)
H5A0.11390.57300.02530.049*
C60.3883 (5)0.52811 (18)0.07245 (14)0.0419 (7)
H6A0.45270.58740.07520.050*
C70.4950 (5)0.45229 (18)0.09736 (13)0.0370 (6)
H7A0.63370.45920.11630.044*
C80.3999 (4)0.36339 (16)0.09509 (12)0.0293 (5)
C90.5017 (4)0.28340 (17)0.12220 (13)0.0318 (5)
H9A0.64110.28840.14090.038*
C100.4039 (4)0.19941 (17)0.12208 (12)0.0303 (5)
H10A0.47490.14680.14100.036*
C110.0855 (4)0.10034 (16)0.09522 (12)0.0276 (5)
H11A−0.05120.09610.07430.033*
C120.0344 (4)−0.05514 (15)0.12429 (12)0.0272 (5)
H12A−0.0933−0.04320.09390.033*
C13−0.0418 (4)−0.07285 (16)0.20294 (12)0.0319 (5)
H13A0.0611−0.04070.23540.038*
C14−0.0318 (5)−0.17642 (17)0.22220 (13)0.0349 (6)
H14A−0.0942−0.19270.27010.042*
C15−0.0922 (4)−0.24379 (16)0.15923 (13)0.0314 (5)
C160.1384 (4)−0.22704 (16)0.13233 (14)0.0312 (5)
H16A0.2087−0.28180.10980.037*
C170.1577 (4)−0.13693 (16)0.09012 (13)0.0323 (5)
H17A0.1047−0.14710.04050.039*
H17B0.3090−0.11990.08670.039*
C180.2002 (5)−0.20788 (18)0.21145 (15)0.0394 (6)
H18A0.3060−0.15800.21760.047*
H18B0.2396−0.26380.23920.047*
C19−0.2562 (5)−0.0283 (2)0.21626 (17)0.0468 (7)
H19A−0.25080.03700.20220.070*
H19B−0.2918−0.03300.26760.070*
H19C−0.3640−0.06020.18760.070*
C20−0.1237 (5)−0.34257 (18)0.18812 (16)0.0450 (7)
H20A−0.0073−0.35830.22080.068*
H20B−0.1256−0.38620.14770.068*
H20C−0.2581−0.34620.21420.068*
C21−0.2736 (4)−0.22375 (19)0.10794 (16)0.0408 (7)
H21A−0.2636−0.15970.09090.061*
H21B−0.4083−0.23270.13310.061*
H21C−0.2659−0.26590.06660.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0296 (11)0.0260 (9)0.0304 (9)−0.0025 (8)0.0004 (9)0.0014 (8)
C10.0312 (13)0.0279 (11)0.0235 (10)−0.0026 (10)0.0044 (9)−0.0008 (9)
C20.0284 (12)0.0291 (11)0.0260 (10)−0.0010 (10)0.0007 (9)−0.0015 (8)
C30.0348 (14)0.0273 (11)0.0229 (10)−0.0009 (10)0.0071 (10)−0.0025 (9)
C40.0411 (15)0.0308 (12)0.0322 (12)0.0025 (12)0.0068 (11)0.0012 (9)
C50.0575 (19)0.0277 (12)0.0371 (13)0.0035 (13)0.0123 (13)0.0020 (11)
C60.060 (2)0.0280 (12)0.0378 (13)−0.0116 (13)0.0161 (13)−0.0031 (10)
C70.0407 (15)0.0393 (14)0.0309 (11)−0.0142 (12)0.0090 (11)−0.0048 (10)
C80.0336 (13)0.0311 (12)0.0230 (9)−0.0051 (10)0.0067 (10)−0.0025 (9)
C90.0286 (12)0.0386 (13)0.0282 (11)−0.0035 (11)−0.0001 (10)−0.0008 (10)
C100.0311 (13)0.0315 (11)0.0285 (10)−0.0002 (10)−0.0004 (11)0.0031 (9)
C110.0296 (12)0.0293 (11)0.0239 (9)−0.0019 (10)0.0009 (9)−0.0026 (9)
C120.0280 (12)0.0255 (10)0.0281 (10)−0.0003 (9)−0.0011 (10)0.0005 (9)
C130.0397 (14)0.0274 (11)0.0285 (11)−0.0049 (11)0.0032 (10)−0.0029 (9)
C140.0483 (16)0.0284 (11)0.0279 (11)−0.0068 (11)0.0007 (11)0.0033 (9)
C150.0333 (14)0.0250 (11)0.0359 (12)−0.0027 (10)0.0016 (11)−0.0017 (9)
C160.0299 (13)0.0251 (11)0.0388 (12)0.0015 (10)−0.0027 (11)−0.0015 (9)
C170.0326 (14)0.0300 (12)0.0342 (12)0.0008 (10)0.0057 (10)−0.0019 (10)
C180.0443 (16)0.0305 (12)0.0433 (14)−0.0023 (11)−0.0163 (13)0.0074 (11)
C190.0514 (19)0.0365 (14)0.0526 (16)−0.0018 (13)0.0220 (14)−0.0080 (13)
C200.0529 (19)0.0296 (13)0.0526 (15)−0.0079 (13)0.0056 (14)0.0004 (11)
C210.0316 (14)0.0349 (14)0.0560 (17)−0.0052 (12)−0.0066 (12)−0.0088 (12)
Geometric parameters (Å, º) top
N1—C111.268 (3)C13—C191.521 (4)
N1—C121.466 (3)C13—C141.541 (3)
C1—C21.371 (3)C13—H13A1.0000
C1—C101.424 (3)C14—C181.549 (4)
C1—C111.473 (3)C14—C151.568 (3)
C2—C31.424 (3)C14—H14A1.0000
C2—H2A0.9500C15—C211.518 (4)
C3—C41.421 (4)C15—C201.538 (3)
C3—C81.423 (4)C15—C161.560 (4)
C4—C51.373 (4)C16—C171.525 (3)
C4—H4A0.9500C16—C181.543 (4)
C5—C61.402 (5)C16—H16A1.0000
C5—H5A0.9500C17—H17A0.9900
C6—C71.368 (4)C17—H17B0.9900
C6—H6A0.9500C18—H18A0.9900
C7—C81.419 (3)C18—H18B0.9900
C7—H7A0.9500C19—H19A0.9800
C8—C91.416 (4)C19—H19B0.9800
C9—C101.363 (3)C19—H19C0.9800
C9—H9A0.9500C20—H20A0.9800
C10—H10A0.9500C20—H20B0.9800
C11—H11A0.9500C20—H20C0.9800
C12—C171.552 (3)C21—H21A0.9800
C12—C131.557 (3)C21—H21B0.9800
C12—H12A1.0000C21—H21C0.9800
C11—N1—C12117.0 (2)C13—C14—C15114.9 (2)
C2—C1—C10119.6 (2)C18—C14—C1587.28 (19)
C2—C1—C11119.4 (2)C13—C14—H14A114.8
C10—C1—C11120.9 (2)C18—C14—H14A114.8
C1—C2—C3121.1 (2)C15—C14—H14A114.8
C1—C2—H2A119.4C21—C15—C20107.3 (2)
C3—C2—H2A119.4C21—C15—C16118.4 (2)
C4—C3—C8119.1 (2)C20—C15—C16112.1 (2)
C4—C3—C2122.1 (2)C21—C15—C14122.2 (2)
C8—C3—C2118.8 (2)C20—C15—C14110.4 (2)
C5—C4—C3120.4 (3)C16—C15—C1485.06 (19)
C5—C4—H4A119.8C17—C16—C18108.3 (2)
C3—C4—H4A119.8C17—C16—C15111.8 (2)
C4—C5—C6120.2 (3)C18—C16—C1587.76 (19)
C4—C5—H5A119.9C17—C16—H16A115.3
C6—C5—H5A119.9C18—C16—H16A115.3
C7—C6—C5121.0 (3)C15—C16—H16A115.3
C7—C6—H6A119.5C16—C17—C12113.7 (2)
C5—C6—H6A119.5C16—C17—H17A108.8
C6—C7—C8120.4 (3)C12—C17—H17A108.8
C6—C7—H7A119.8C16—C17—H17B108.8
C8—C7—H7A119.8C12—C17—H17B108.8
C9—C8—C7122.4 (2)H17A—C17—H17B107.7
C9—C8—C3118.7 (2)C16—C18—C1486.27 (19)
C7—C8—C3118.8 (2)C16—C18—H18A114.3
C10—C9—C8121.4 (2)C14—C18—H18A114.3
C10—C9—H9A119.3C16—C18—H18B114.3
C8—C9—H9A119.3C14—C18—H18B114.3
C9—C10—C1120.3 (2)H18A—C18—H18B111.4
C9—C10—H10A119.8C13—C19—H19A109.5
C1—C10—H10A119.8C13—C19—H19B109.5
N1—C11—C1122.7 (2)H19A—C19—H19B109.5
N1—C11—H11A118.6C13—C19—H19C109.5
C1—C11—H11A118.6H19A—C19—H19C109.5
N1—C12—C17109.8 (2)H19B—C19—H19C109.5
N1—C12—C13108.75 (18)C15—C20—H20A109.5
C17—C12—C13114.37 (19)C15—C20—H20B109.5
N1—C12—H12A107.9H20A—C20—H20B109.5
C17—C12—H12A107.9C15—C20—H20C109.5
C13—C12—H12A107.9H20A—C20—H20C109.5
C19—C13—C14114.2 (2)H20B—C20—H20C109.5
C19—C13—C12111.0 (2)C15—C21—H21A109.5
C14—C13—C12111.37 (19)C15—C21—H21B109.5
C19—C13—H13A106.6H21A—C21—H21B109.5
C14—C13—H13A106.6C15—C21—H21C109.5
C12—C13—H13A106.6H21A—C21—H21C109.5
C13—C14—C18107.1 (2)H21B—C21—H21C109.5
C10—C1—C2—C3−1.9 (3)N1—C12—C13—C14−138.8 (2)
C11—C1—C2—C3177.1 (2)C17—C12—C13—C14−15.7 (3)
C1—C2—C3—C4−178.0 (2)C19—C13—C14—C18−175.4 (2)
C1—C2—C3—C81.3 (3)C12—C13—C14—C1857.9 (3)
C8—C3—C4—C5−1.6 (3)C19—C13—C14—C1589.6 (3)
C2—C3—C4—C5177.6 (2)C12—C13—C14—C15−37.1 (3)
C3—C4—C5—C60.8 (4)C13—C14—C15—C21−40.3 (4)
C4—C5—C6—C70.6 (4)C18—C14—C15—C21−147.9 (2)
C5—C6—C7—C8−1.3 (4)C13—C14—C15—C20−167.8 (2)
C6—C7—C8—C9−178.1 (2)C18—C14—C15—C2084.6 (3)
C6—C7—C8—C30.5 (3)C13—C14—C15—C1680.4 (2)
C4—C3—C8—C9179.6 (2)C18—C14—C15—C16−27.21 (17)
C2—C3—C8—C90.3 (3)C21—C15—C16—C1742.6 (3)
C4—C3—C8—C70.9 (3)C20—C15—C16—C17168.4 (2)
C2—C3—C8—C7−178.3 (2)C14—C15—C16—C17−81.6 (2)
C7—C8—C9—C10177.3 (2)C21—C15—C16—C18151.4 (2)
C3—C8—C9—C10−1.3 (3)C20—C15—C16—C18−82.7 (2)
C8—C9—C10—C10.7 (3)C14—C15—C16—C1827.31 (17)
C2—C1—C10—C90.9 (3)C18—C16—C17—C12−53.0 (3)
C11—C1—C10—C9−178.1 (2)C15—C16—C17—C1242.1 (3)
C12—N1—C11—C1177.13 (19)N1—C12—C17—C16136.0 (2)
C2—C1—C11—N1−176.8 (2)C13—C12—C17—C1613.4 (3)
C10—C1—C11—N12.2 (3)C17—C16—C18—C1484.6 (2)
C11—N1—C12—C17126.8 (2)C15—C16—C18—C14−27.62 (17)
C11—N1—C12—C13−107.3 (2)C13—C14—C18—C16−87.8 (2)
N1—C12—C13—C1992.7 (2)C15—C14—C18—C1627.48 (17)
C17—C12—C13—C19−144.1 (2)
Relative orientation (°) between the naphthyl group and the ring bonded to the chiral C atom C12 in compounds (1)–(8). top
Angles τ1 and τ2 are torsion angles N1—C12—C14—C(ring) or equivalent angles for compounds (1) and (8), which have four molecules in the asymmetric unit. The dihedral angle δ is calculated between the mean planes of the naphthyl group and the ring bonded to C12.
Moleculeτ1 (+ac)τ2 (-sc)δ
(1)/N1110.0 (5)-67.2 (5)78.22 (11)
(1)/N2140.7 (4)-41.5 (5)58.23 (11)
(1)/N3142.0 (4)-40.0 (6)43.7 (3)
(1)/N4110.0 (6)-64.6 (8)74.97 (18)
(2)98.3 (4)-77.7 (4)80.49 (7)
(3)a111.5 (5)-67.0 (6)60.16 (13)
(4)a150.1 (5)-33.7 (7)45.91 (15)
(5)97.9 (5)-77.9 (6)80.99 (10)
(6)98.1 (6)-79.2 (6)81.04 (11)
(7)b155.4 (3)-27.4 (4)67.44 (6)
(8)/N160 (2)-66 (2)88.6 (6)
(8)/N2169.6 (9)-62.6 (12)48.0 (3)
(8)/N370.0 (12)-55.6 (13)88.2 (3)
(8)/N4165.1 (14)22 (3)66.7 (6)
Notes: (a) Refined model has been inverted in order to compare S-C12 molecules. (b) The dihedral angle δ is computed between the two naphthyl ring systems.
 

Acknowledgements

Thanks are due to VIEP–UAP for financial support. SB acknowledges support by the Instituto de Física Luis Rivera Terrazas (Puebla, Mexico).

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ISSN: 2056-9890
Volume 72| Part 4| April 2016| Pages 583-589
https://doi.org/10.1107/S2056989016004692
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