research communications
2,7.018,23]hexacosa-2,4,6,18(23),19,21,24(1),25,27-nonaene
of 26-(4-methylphenyl)-8,11,14,17-tetraoxa-28-azatetracyclo[22.3.1.0aFaculty of Chemistry, University of Science, Vietnam National University, 19 Le Thanh Tong, Hanoi, Vietnam, bInstitute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam, and cOrganic Chemistry Department, Peoples Friendship University of Russia, Miklukho-Maklaya St. 6, Moscow 117198, Russian Federation
*Correspondence e-mail: tvche@yahoo.com
The title compound, C30H29NO4, is a tetracyclic system containing a 4-arylpyridine fragment, two benzene rings and an aza-17-crown-5 ether moiety, in a bowl-like arrangement. The pyridine ring is inclined to the 4-methylphenyl ring by 26.64 (6)°, and by 57.43 (6) and 56.81 (6)° to the benzene rings. The benzene rings are inclined to one another by 88.32 (6)°. In the crystal, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with an R22(14) ring motif. The dimers are linked via a number of C—H⋯π interactions, forming a three-dimensional architecture.
Keywords: crystal structure; 4-arylpyridine; aza-17-crown-5 ether; Chichibabin domino reaction; C—H⋯N hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1472697
1. Chemical context
Over the last decades, there has been considerable interest in pyridino-fused azacrown et al., 1993). Among them, pyridinocrownophanes containing a benzo subunit show high effectiveness as complexating ligands in metal-ion capture and separation (Pedersen, 1988). They are also of interest as phase-transfer catalysts, as membrane ion transporting vehicles (Gokel & Murillo, 1996), as active components useful in environmental chemistry (Bradshaw & Izatt, 1997), in design technology for the construction of organic sensors (Costero et al., 2005) and as nanosized on–off switches and other molecular electronic devices (Natali & Giordani, 2012). It has also been shown that the family of pyridinoazacrown compounds can possess antibacterial (An et al., 1998) and anticancer properties (Artiemenko et al., 2002; Le et al., 2015).
owing to their great theoretical and practical potential (BradshawRecently, we have proposed a new efficient one-step Chichibabin method for the preparation of a series of pyridinocrownophanes incorporating a 14-crown-4 ether moiety (Le et al., 2014, 2015; Anh et al., 2008; Levov et al., 2008). During the course of our attempts to develop the chemistry of these azacrown systems and obtain macrocyclic ligands which include more extended macro-heterocycles, namely the 17-crown-5 ether moiety, we have studied the Chichibabin-type condensation of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane with 4-methylbenzaldehyde and ammonium acetate in acetic acid. This reaction (Fig. 1) proceeds smoothly under heating of the multicomponent mixture to give the expected azacrown with reasonable yield (30%). Herein, we report on the synthesis and of this new azacrown compound (I).
2. Structural commentary
The molecule of the title compound, (I), is a tetracyclic system containing a 4-arylpyridine fragment (rings A = N22/C17–C22 and B = C23–C28), two benzene rings (C = C11–C16 and D = C30–C35), and an aza-17-crown-5 ether moiety, and has a bowl-like arrangement (Fig. 2). While the dihedral angles between the benzene rings and the pyridine ring are A/D = 56.81 (6)° and A/C = 57.43 (6)°, the dihedral angle between the 4-methylphenyl ring (B) and the pyridine ring (A) in the 4-arylpyridine fragment is only 26.64 (6)°. The distances from the center of the macrocycle cavity, defined as the centroid of atoms O1/O4/O7/O10/N22, to the individual atoms O1, O4, O7, O10 and N22 are 2.813 (2), 2.549 (2), 2.588 (2), 2.517 (2) and 2.825 (2) Å, respectively.
3. Supramolecular features
In the crystal, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with an R22(14) ring motif (Table 1 and Fig. 3). The dimers are linked via a number of C—H⋯π interactions, forming a three-dimensional structure (Table 1).
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016) for the macrocyclic S1, illustrated in Fig. 4, gave three hits, viz. 2,4,15,17,20-pentamethyl-6,7,9,10,12,13,20,21-octahydro-19H-dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (DORPOQ; Rungsimanon et al., 2008), 25,27-dimethyl-8,11,14,17-tetraoxa-28-azatetracyclo(22.3.1.02,7.018,23)octacosa-2,4,6,18 (23),19,21-hexen-26-one (EFIJEV; Levov et al., 2008), and 20-cyclohexyl-2,4,15,17-tetramethyl-6,7,9,10,12,13,20,21-octahydro-19H-dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (KUFWIS; Chirachanchai et al., 2009), also illustrated in Fig. 4. The two benzene rings are inclined to one another by 50.41 (6)° in DORPOQ, 88.28 (9)° in EFIJEV and 74.3 (9)° in KUGWIS. The corresponding dihedral angle in the title compound [D/C = 88.32 (6)°] is similar to that observed in EFIJEV.
5. Synthesis and crystallization
The synthesis of the title compound (I), is illustrated in Fig. 1. Ammonium acetate (10.0 g, 130 mmol) was added to a solution of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane (0.50 g, 1.30 mmol) and p-methylbenzaldehyde (0.155 g, 1.30 mmol) in acetic acid (10 ml). The reaction mixture was then refluxed for 45 min (monitored by TLC until disappearance of the starting diketone spot). At the end of the reaction, the reaction mixture was left to cool to room temperature, neutralized with Na2CO3 and extracted with ethyl acetate. The extract was purified by on silica gel to give colourless crystals of the title compound (I) [yield 0.18 g, 30%; m.p. 471–472 K]. IR (KBr), ν cm−1: C=Npyridine (1607), C=Caromatic (1545, 1514, 1492), C—O—C (1182, 1120, 1058, 1029). 1H NMR (CDCl3, 500 MHz, 300 K): d = 2.42 (s, 3H, CH3), 3.18 (s, 4H, Hether), 3.62 and 4.11 (both t, 4H each, Hether, J = 8 Hz each), 7.0–6.98 (d, 2H, Harom), 7.13–7.10 (m, 2H, Harom), 7.30–7.29 (d, 2H, Harom), 7.37–7.34 (m, 2H, Harom), 7.66–7.62 (m, 4H, Harom), 7.75 (s, 2H, H25, 27). ESI–MS: [M + H]+ = 468.2. Analysis calculated for C30H29NO4: C, 77.07; H, 6.25; N, 3.00. Found: C, 77.22; H, 6.05; N, 3.12.
6. Refinement
Crystal data, data collection and structure . The H atoms were placed in calculated positions and refined as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1472697
10.1107/S2056989016005752/su5294sup1.cif
contains datablocks Global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016005752/su5294Isup2.hkl
Over the last decades, there has been considerable interest in pyridino-fused azacrown
owing to their great theoretical and practical potential (Bradshaw et al., 1993). Among them, pyridinocrownophanes containing a benzo subunit show high effectiveness as complexating ligands in metal-ion capture and separation (Pedersen, 1988). They are also of interest as phase-transfer catalysts, as membrane ion transporting vehicles (Gokel & Murillo, 1996), as active components useful in environmental chemistry (Bradshaw & Izatt, 1997), in design technology for the construction of organic sensors (Costero et al., 2005) and as nanosized on–off switches and other molecular electronic devices (Natali & Giordani, 2012). It has also been shown that the family of pyridinoazacrown compounds can possess antibacterial (An et al., 1998) and anticancer properties (Artiemenko et al., 2002; Le et al., 2015).Recently, we have proposed a new efficient one-step Chichibabin method for the preparation of a series of pyridinocrownophanes incorporating a 14-crown-4 ether moiety (Le et al., 2014, 2015; Anh et al., 2008; Levov et al., 2008). During the course of our attempts to develop the chemistry of these azacrown systems and obtain macrocyclic ligands which include more extended macro-heterocycles, namely the 17-crown-5 ether moiety, we have studied the Chichibabin-type condensation of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane with 4-methylbenzaldehyde and ammonium acetate in acetic acid. This reaction (Fig. 1) proceeds smoothly under heating of the multicomponent mixture to give the expected azacrown with reasonable yield (30%). Herein, we report on the synthesis and
of this new azacrown compound (I).The molecule of the title compound, (I), comprises a fused tetracyclic system containing a 4-arylpyridine fragment (rings A = N22/C17–C22 and B = C23–C28), two benzene rings (C = C11–C16 and D = C30–C35), and an aza-17-crown-5 ether moiety, and has a bowl-like arrangement (Fig. 2). While the dihedral angles between the benzene rings and the pyridine ring are A/D = 56.81 (6)° and A/C = 57.43 (6)°, the dihedral angle between 4-methylphenyl ring (B) and and pyridine ring (A) in the 4-arylpyridine fragment is only 26.64 (6)°. The distances from the center of the macrocycle cavity, defined as the centroid of atoms O1/O4/O7/O10/N22, to the individual atoms O1, O4, O7, O10 and N22 are 2.813 (2), 2.549 (2), 2.588 (2), 2.517 (2) and 2.825 (2) Å, respectively.
In the crystal, molecules are linked by pairs of C—H···N hydrogen bonds, forming inversion dimers with an R22(14) ring motif (Table 1 and Fig. 3). The dimers are linked via a number of C—H···π interactions, forming a three-dimensional structure (Table 1).
\ A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016) for the macrocyclic
S1, illustrated in Fig. 4, gave three hits, viz. 2,4,15,17,20-pentamethyl-6,7,9,10,12,13,20,21-octahydro-19H-\ dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (DORPOQ; Rungsimanon et al., 2008), 25,27-dimethyl-8,11,14,17-tetraoxa-28-azatetracyclo(22.3.1.02,7.018,23)\ octacosa-2,4,6,18 (23),19,21-hexen-26-one (EFIJEV; Levov et al., 2008), and 20-cyclohexyl-2,4,15,17-tetramethyl-6,7,9,10,12,13,20,21-octahydro-\ 19H-dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (KUFWIS; Chirachanchai et al., 2009), also illustrated in Fig. 4. The two benzene rings are inclined to one another by 50.41 (6)° in DORPOQ, 88.28 (9)° in EFIJEV and 74.3 (9)° in KUGWIS. The corresponding dihedral angle in the title compound [D/C = 88.32 (6)°] is similar to that observed in EFIJEV.The synthesis of the title compound (I), is illustrated in Fig. 1. Ammonium acetate (10.0 g, 130 mmol) was added to a solution of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane (0.50 g, 1.30 mmol) and p-methylbenzaldehyde (0.155 g, 1.30 mmol) in acetic acid (10 ml). The reaction mixture was then refluxed for 45 min (monitored by TLC until disappearance of the starting diketone spot). At the end of the reaction, the reaction mixture was left to cool to room temperature, neutralized with Na2CO3 and extracted with ethyl acetate. The extract was purified by ν cm-1: C═ Npyridine (1607), C═Caromatic (1545, 1514, 1492), C—O—C (1182, 1120, 1058, 1029). 1H NMR (CDCl3 , 500 MHz, 300 K): d = 2.42 (s, 3H, CH3), 3.18 (s, 4H, Hether), 3.62 and 4.11 (both t, 4H each, Hether, J = 8 Hz each), 7.0–6.98 (d, 2H, Harom), 7.13–7.10 (m, 2H, Harom), 7.30–7.29 (d, 2H, Harom), 7.37–7.34 (m, 2H, Harom), 7.66–7.62 (m, 4H, Harom), 7.75 (s, 2H, H25, 27). ESI–MS: [M + H]+ = 468.2. Analysis calculated for C30H29NO4 : C, 77.07; H, 6.25; N, 3.00. Found: C, 77.22; H, 6.05; N, 3.12.
on silica gel to give colourless crystals of the title compound (I) [yield 0.18 g, 30%; m.p. 471–472 K]. IR (KBr),Over the last decades, there has been considerable interest in pyridino-fused azacrown
owing to their great theoretical and practical potential (Bradshaw et al., 1993). Among them, pyridinocrownophanes containing a benzo subunit show high effectiveness as complexating ligands in metal-ion capture and separation (Pedersen, 1988). They are also of interest as phase-transfer catalysts, as membrane ion transporting vehicles (Gokel & Murillo, 1996), as active components useful in environmental chemistry (Bradshaw & Izatt, 1997), in design technology for the construction of organic sensors (Costero et al., 2005) and as nanosized on–off switches and other molecular electronic devices (Natali & Giordani, 2012). It has also been shown that the family of pyridinoazacrown compounds can possess antibacterial (An et al., 1998) and anticancer properties (Artiemenko et al., 2002; Le et al., 2015).Recently, we have proposed a new efficient one-step Chichibabin method for the preparation of a series of pyridinocrownophanes incorporating a 14-crown-4 ether moiety (Le et al., 2014, 2015; Anh et al., 2008; Levov et al., 2008). During the course of our attempts to develop the chemistry of these azacrown systems and obtain macrocyclic ligands which include more extended macro-heterocycles, namely the 17-crown-5 ether moiety, we have studied the Chichibabin-type condensation of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane with 4-methylbenzaldehyde and ammonium acetate in acetic acid. This reaction (Fig. 1) proceeds smoothly under heating of the multicomponent mixture to give the expected azacrown with reasonable yield (30%). Herein, we report on the synthesis and
of this new azacrown compound (I).The molecule of the title compound, (I), comprises a fused tetracyclic system containing a 4-arylpyridine fragment (rings A = N22/C17–C22 and B = C23–C28), two benzene rings (C = C11–C16 and D = C30–C35), and an aza-17-crown-5 ether moiety, and has a bowl-like arrangement (Fig. 2). While the dihedral angles between the benzene rings and the pyridine ring are A/D = 56.81 (6)° and A/C = 57.43 (6)°, the dihedral angle between 4-methylphenyl ring (B) and and pyridine ring (A) in the 4-arylpyridine fragment is only 26.64 (6)°. The distances from the center of the macrocycle cavity, defined as the centroid of atoms O1/O4/O7/O10/N22, to the individual atoms O1, O4, O7, O10 and N22 are 2.813 (2), 2.549 (2), 2.588 (2), 2.517 (2) and 2.825 (2) Å, respectively.
In the crystal, molecules are linked by pairs of C—H···N hydrogen bonds, forming inversion dimers with an R22(14) ring motif (Table 1 and Fig. 3). The dimers are linked via a number of C—H···π interactions, forming a three-dimensional structure (Table 1).
\ A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016) for the macrocyclic
S1, illustrated in Fig. 4, gave three hits, viz. 2,4,15,17,20-pentamethyl-6,7,9,10,12,13,20,21-octahydro-19H-\ dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (DORPOQ; Rungsimanon et al., 2008), 25,27-dimethyl-8,11,14,17-tetraoxa-28-azatetracyclo(22.3.1.02,7.018,23)\ octacosa-2,4,6,18 (23),19,21-hexen-26-one (EFIJEV; Levov et al., 2008), and 20-cyclohexyl-2,4,15,17-tetramethyl-6,7,9,10,12,13,20,21-octahydro-\ 19H-dibenzo[k,p][1,4,7,10,14]tetraoxazacycloheptadecine (KUFWIS; Chirachanchai et al., 2009), also illustrated in Fig. 4. The two benzene rings are inclined to one another by 50.41 (6)° in DORPOQ, 88.28 (9)° in EFIJEV and 74.3 (9)° in KUGWIS. The corresponding dihedral angle in the title compound [D/C = 88.32 (6)°] is similar to that observed in EFIJEV.The synthesis of the title compound (I), is illustrated in Fig. 1. Ammonium acetate (10.0 g, 130 mmol) was added to a solution of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane (0.50 g, 1.30 mmol) and p-methylbenzaldehyde (0.155 g, 1.30 mmol) in acetic acid (10 ml). The reaction mixture was then refluxed for 45 min (monitored by TLC until disappearance of the starting diketone spot). At the end of the reaction, the reaction mixture was left to cool to room temperature, neutralized with Na2CO3 and extracted with ethyl acetate. The extract was purified by ν cm-1: C═ Npyridine (1607), C═Caromatic (1545, 1514, 1492), C—O—C (1182, 1120, 1058, 1029). 1H NMR (CDCl3 , 500 MHz, 300 K): d = 2.42 (s, 3H, CH3), 3.18 (s, 4H, Hether), 3.62 and 4.11 (both t, 4H each, Hether, J = 8 Hz each), 7.0–6.98 (d, 2H, Harom), 7.13–7.10 (m, 2H, Harom), 7.30–7.29 (d, 2H, Harom), 7.37–7.34 (m, 2H, Harom), 7.66–7.62 (m, 4H, Harom), 7.75 (s, 2H, H25, 27). ESI–MS: [M + H]+ = 468.2. Analysis calculated for C30H29NO4 : C, 77.07; H, 6.25; N, 3.00. Found: C, 77.22; H, 6.05; N, 3.12.
on silica gel to give colourless crystals of the title compound (I) [yield 0.18 g, 30%; m.p. 471–472 K]. IR (KBr), detailsCrystal data, data collection and structure
details are summarized in Table 2. The H atoms were placed in calculated positions and refined as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).Fig. 1. Chichibabin-type condensation of 1,8-bis(2-acetylphenoxy)-3,6-dioxaoctane with 4-methylbenzaldehyde and ammonium acetate to produce the title compound (I). | |
Fig. 2. Molecular structure of the title compound (I), with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 3. A view along the a axis of the crystal packing of the title compound (I). The C—H···N hydrogen bonds are shown as dashed lines (see Table 1). | |
Fig. 4. Database search substructure S1, and results. |
C30H29NO4 | F(000) = 992 |
Mr = 467.54 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0819 (4) Å | Cell parameters from 9281 reflections |
b = 10.4531 (4) Å | θ = 2.9–28.3° |
c = 23.6016 (9) Å | µ = 0.08 mm−1 |
β = 100.607 (1)° | T = 100 K |
V = 2444.80 (16) Å3 | Block, colourless |
Z = 4 | 0.14 × 0.12 × 0.12 mm |
D8 Quest Bruker CMOS diffractometer | 4706 reflections with I > 2σ(I) |
Detector resolution: 0.5 pixels mm-1 | Rint = 0.043 |
ω and φ scans | θmax = 27.9°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −13→13 |
Tmin = 0.695, Tmax = 0.746 | k = −13→13 |
77012 measured reflections | l = −31→30 |
5825 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0422P)2 + 1.1744P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
5825 reflections | Δρmax = 0.31 e Å−3 |
317 parameters | Δρmin = −0.19 e Å−3 |
C30H29NO4 | V = 2444.80 (16) Å3 |
Mr = 467.54 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.0819 (4) Å | µ = 0.08 mm−1 |
b = 10.4531 (4) Å | T = 100 K |
c = 23.6016 (9) Å | 0.14 × 0.12 × 0.12 mm |
β = 100.607 (1)° |
D8 Quest Bruker CMOS diffractometer | 5825 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 4706 reflections with I > 2σ(I) |
Tmin = 0.695, Tmax = 0.746 | Rint = 0.043 |
77012 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.31 e Å−3 |
5825 reflections | Δρmin = −0.19 e Å−3 |
317 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.76598 (8) | 0.67651 (8) | 0.70887 (4) | 0.02073 (19) | |
C2 | 0.90811 (12) | 0.64977 (12) | 0.71765 (6) | 0.0236 (3) | |
H2A | 0.9585 | 0.7123 | 0.7450 | 0.028* | |
H2B | 0.9407 | 0.6561 | 0.6807 | 0.028* | |
C3 | 0.93002 (13) | 0.51576 (13) | 0.74174 (6) | 0.0260 (3) | |
H3A | 1.0261 | 0.5060 | 0.7600 | 0.031* | |
H3B | 0.8752 | 0.5042 | 0.7721 | 0.031* | |
O4 | 0.89565 (10) | 0.41796 (9) | 0.69952 (4) | 0.0283 (2) | |
C5 | 0.75342 (13) | 0.40022 (13) | 0.68115 (6) | 0.0254 (3) | |
H5A | 0.7148 | 0.4735 | 0.6570 | 0.030* | |
H5B | 0.7088 | 0.3956 | 0.7151 | 0.030* | |
C6 | 0.72925 (15) | 0.27780 (13) | 0.64690 (6) | 0.0276 (3) | |
H6A | 0.7722 | 0.2065 | 0.6712 | 0.033* | |
H6B | 0.6310 | 0.2610 | 0.6382 | 0.033* | |
O7 | 0.77874 (10) | 0.27738 (9) | 0.59417 (4) | 0.0294 (2) | |
C8 | 0.71355 (13) | 0.36342 (13) | 0.55114 (5) | 0.0240 (3) | |
H8A | 0.7674 | 0.3683 | 0.5201 | 0.029* | |
H8B | 0.7137 | 0.4497 | 0.5685 | 0.029* | |
C9 | 0.57024 (12) | 0.32947 (12) | 0.52436 (5) | 0.0191 (2) | |
H9A | 0.5462 | 0.3679 | 0.4855 | 0.023* | |
H9B | 0.5602 | 0.2355 | 0.5206 | 0.023* | |
O10 | 0.48389 (8) | 0.37838 (9) | 0.56118 (4) | 0.0226 (2) | |
C11 | 0.71707 (12) | 0.77257 (11) | 0.67121 (5) | 0.0169 (2) | |
C12 | 0.79826 (12) | 0.86832 (12) | 0.65433 (5) | 0.0202 (2) | |
H12 | 0.8924 | 0.8694 | 0.6694 | 0.024* | |
C13 | 0.74163 (13) | 0.96191 (12) | 0.61564 (5) | 0.0216 (3) | |
H13 | 0.7973 | 1.0267 | 0.6041 | 0.026* | |
C14 | 0.60453 (13) | 0.96142 (12) | 0.59371 (5) | 0.0223 (3) | |
H14 | 0.5656 | 1.0261 | 0.5675 | 0.027* | |
C15 | 0.52418 (12) | 0.86528 (12) | 0.61036 (5) | 0.0200 (2) | |
H15 | 0.4303 | 0.8646 | 0.5949 | 0.024* | |
C16 | 0.57788 (12) | 0.77018 (11) | 0.64904 (5) | 0.0167 (2) | |
C17 | 0.48787 (11) | 0.66625 (11) | 0.66367 (5) | 0.0164 (2) | |
C18 | 0.47440 (12) | 0.64112 (11) | 0.72038 (5) | 0.0177 (2) | |
H18 | 0.5257 | 0.6882 | 0.7513 | 0.021* | |
C19 | 0.38500 (11) | 0.54616 (11) | 0.73144 (5) | 0.0173 (2) | |
C20 | 0.31490 (12) | 0.47876 (11) | 0.68404 (5) | 0.0182 (2) | |
H20 | 0.2526 | 0.4137 | 0.6895 | 0.022* | |
C21 | 0.33672 (11) | 0.50726 (11) | 0.62894 (5) | 0.0170 (2) | |
N22 | 0.41964 (10) | 0.60176 (9) | 0.61821 (4) | 0.0168 (2) | |
C23 | 0.36716 (11) | 0.51592 (12) | 0.79121 (5) | 0.0182 (2) | |
C24 | 0.39161 (13) | 0.60818 (13) | 0.83481 (5) | 0.0233 (3) | |
H24 | 0.4182 | 0.6920 | 0.8261 | 0.028* | |
C25 | 0.37740 (14) | 0.57841 (14) | 0.89078 (5) | 0.0264 (3) | |
H25 | 0.3930 | 0.6428 | 0.9196 | 0.032* | |
C26 | 0.34073 (12) | 0.45582 (14) | 0.90541 (5) | 0.0243 (3) | |
C27 | 0.31736 (12) | 0.36405 (13) | 0.86220 (6) | 0.0231 (3) | |
H27 | 0.2930 | 0.2797 | 0.8713 | 0.028* | |
C28 | 0.32895 (12) | 0.39334 (12) | 0.80585 (5) | 0.0207 (3) | |
H28 | 0.3107 | 0.3293 | 0.7769 | 0.025* | |
C29 | 0.32647 (14) | 0.42573 (16) | 0.96669 (6) | 0.0331 (3) | |
H29A | 0.4159 | 0.4246 | 0.9914 | 0.050* | |
H29B | 0.2837 | 0.3418 | 0.9679 | 0.050* | |
H29C | 0.2705 | 0.4913 | 0.9804 | 0.050* | |
C30 | 0.26916 (12) | 0.43182 (11) | 0.57809 (5) | 0.0177 (2) | |
C31 | 0.12989 (13) | 0.42073 (12) | 0.56426 (6) | 0.0241 (3) | |
H31 | 0.0755 | 0.4597 | 0.5883 | 0.029* | |
C32 | 0.06873 (13) | 0.35301 (13) | 0.51548 (6) | 0.0279 (3) | |
H32 | −0.0268 | 0.3469 | 0.5062 | 0.034* | |
C33 | 0.14684 (13) | 0.29501 (12) | 0.48079 (6) | 0.0240 (3) | |
H33 | 0.1047 | 0.2502 | 0.4473 | 0.029* | |
C34 | 0.28687 (13) | 0.30147 (12) | 0.49435 (5) | 0.0208 (3) | |
H34 | 0.3404 | 0.2600 | 0.4707 | 0.025* | |
C35 | 0.34786 (12) | 0.36931 (11) | 0.54301 (5) | 0.0180 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0174 (4) | 0.0189 (4) | 0.0258 (4) | −0.0004 (3) | 0.0037 (3) | 0.0035 (3) |
C2 | 0.0177 (6) | 0.0225 (6) | 0.0299 (7) | −0.0001 (5) | 0.0023 (5) | 0.0013 (5) |
C3 | 0.0239 (6) | 0.0238 (7) | 0.0276 (7) | 0.0010 (5) | −0.0024 (5) | 0.0017 (5) |
O4 | 0.0277 (5) | 0.0221 (5) | 0.0332 (5) | 0.0041 (4) | 0.0006 (4) | −0.0031 (4) |
C5 | 0.0277 (7) | 0.0229 (6) | 0.0242 (6) | 0.0009 (5) | 0.0012 (5) | −0.0007 (5) |
C6 | 0.0370 (8) | 0.0201 (6) | 0.0235 (6) | 0.0021 (6) | −0.0002 (5) | 0.0027 (5) |
O7 | 0.0303 (5) | 0.0283 (5) | 0.0280 (5) | 0.0122 (4) | 0.0016 (4) | −0.0012 (4) |
C8 | 0.0213 (6) | 0.0281 (7) | 0.0244 (6) | 0.0036 (5) | 0.0092 (5) | 0.0040 (5) |
C9 | 0.0227 (6) | 0.0193 (6) | 0.0174 (5) | 0.0030 (5) | 0.0090 (5) | 0.0013 (5) |
O10 | 0.0162 (4) | 0.0311 (5) | 0.0214 (4) | 0.0001 (4) | 0.0057 (3) | −0.0089 (4) |
C11 | 0.0196 (6) | 0.0140 (5) | 0.0176 (5) | −0.0007 (4) | 0.0050 (4) | −0.0024 (4) |
C12 | 0.0189 (6) | 0.0180 (6) | 0.0247 (6) | −0.0031 (5) | 0.0067 (5) | −0.0046 (5) |
C13 | 0.0281 (6) | 0.0150 (6) | 0.0245 (6) | −0.0049 (5) | 0.0120 (5) | −0.0021 (5) |
C14 | 0.0288 (7) | 0.0174 (6) | 0.0216 (6) | 0.0010 (5) | 0.0071 (5) | 0.0030 (5) |
C15 | 0.0198 (6) | 0.0202 (6) | 0.0205 (6) | −0.0005 (5) | 0.0046 (5) | −0.0015 (5) |
C16 | 0.0195 (6) | 0.0156 (5) | 0.0167 (5) | −0.0021 (4) | 0.0075 (4) | −0.0029 (4) |
C17 | 0.0148 (5) | 0.0156 (5) | 0.0195 (6) | 0.0008 (4) | 0.0052 (4) | −0.0008 (4) |
C18 | 0.0173 (5) | 0.0180 (6) | 0.0179 (5) | −0.0012 (4) | 0.0040 (4) | −0.0019 (4) |
C19 | 0.0153 (5) | 0.0181 (6) | 0.0195 (6) | 0.0017 (4) | 0.0060 (4) | −0.0002 (4) |
C20 | 0.0163 (5) | 0.0172 (6) | 0.0229 (6) | −0.0023 (4) | 0.0078 (4) | −0.0012 (5) |
C21 | 0.0146 (5) | 0.0165 (6) | 0.0207 (6) | 0.0006 (4) | 0.0055 (4) | −0.0019 (4) |
N22 | 0.0159 (5) | 0.0166 (5) | 0.0188 (5) | −0.0002 (4) | 0.0055 (4) | −0.0014 (4) |
C23 | 0.0141 (5) | 0.0219 (6) | 0.0191 (6) | 0.0009 (4) | 0.0047 (4) | 0.0020 (5) |
C24 | 0.0280 (7) | 0.0218 (6) | 0.0208 (6) | −0.0014 (5) | 0.0064 (5) | 0.0016 (5) |
C25 | 0.0297 (7) | 0.0312 (7) | 0.0186 (6) | −0.0020 (6) | 0.0050 (5) | −0.0008 (5) |
C26 | 0.0160 (6) | 0.0366 (7) | 0.0204 (6) | 0.0007 (5) | 0.0037 (5) | 0.0076 (5) |
C27 | 0.0167 (6) | 0.0256 (6) | 0.0282 (7) | −0.0015 (5) | 0.0069 (5) | 0.0082 (5) |
C28 | 0.0158 (6) | 0.0223 (6) | 0.0252 (6) | −0.0015 (5) | 0.0063 (5) | 0.0006 (5) |
C29 | 0.0280 (7) | 0.0489 (9) | 0.0219 (7) | −0.0044 (6) | 0.0034 (5) | 0.0117 (6) |
C30 | 0.0188 (6) | 0.0154 (5) | 0.0193 (6) | −0.0021 (4) | 0.0047 (4) | −0.0008 (4) |
C31 | 0.0199 (6) | 0.0240 (6) | 0.0298 (7) | −0.0015 (5) | 0.0083 (5) | −0.0059 (5) |
C32 | 0.0171 (6) | 0.0302 (7) | 0.0351 (7) | −0.0035 (5) | 0.0013 (5) | −0.0064 (6) |
C33 | 0.0257 (6) | 0.0225 (6) | 0.0223 (6) | −0.0050 (5) | 0.0004 (5) | −0.0042 (5) |
C34 | 0.0247 (6) | 0.0195 (6) | 0.0190 (6) | −0.0009 (5) | 0.0061 (5) | −0.0020 (5) |
C35 | 0.0180 (6) | 0.0183 (6) | 0.0183 (6) | −0.0019 (4) | 0.0049 (4) | 0.0008 (4) |
O1—C2 | 1.4370 (15) | C18—C19 | 1.3973 (16) |
O1—C11 | 1.3712 (14) | C19—C20 | 1.3987 (17) |
C2—C3 | 1.5126 (18) | C19—C23 | 1.4886 (16) |
C3—O4 | 1.4251 (16) | C20—C21 | 1.3905 (16) |
O4—C5 | 1.4317 (16) | C21—N22 | 1.3479 (15) |
C5—C6 | 1.5093 (18) | C21—C30 | 1.4917 (16) |
C6—O7 | 1.4236 (17) | C23—C24 | 1.3987 (17) |
O7—C8 | 1.4235 (15) | C23—C28 | 1.3995 (17) |
C8—C9 | 1.5089 (17) | C24—C25 | 1.3900 (17) |
C9—O10 | 1.4329 (14) | C25—C26 | 1.3946 (19) |
O10—C35 | 1.3628 (14) | C26—C27 | 1.3883 (19) |
C11—C12 | 1.3966 (16) | C26—C29 | 1.5125 (17) |
C11—C16 | 1.4047 (16) | C27—C28 | 1.3905 (17) |
C12—C13 | 1.3874 (18) | C30—C31 | 1.3867 (17) |
C13—C14 | 1.3839 (18) | C30—C35 | 1.4084 (16) |
C14—C15 | 1.3921 (17) | C31—C32 | 1.3947 (18) |
C15—C16 | 1.3901 (17) | C32—C33 | 1.3768 (19) |
C16—C17 | 1.4962 (16) | C33—C34 | 1.3906 (18) |
C17—C18 | 1.3948 (16) | C34—C35 | 1.3928 (17) |
C17—N22 | 1.3444 (15) | ||
C11—O1—C2 | 117.77 (9) | C20—C19—C23 | 121.31 (11) |
O1—C2—C3 | 107.88 (10) | C21—C20—C19 | 119.77 (11) |
O4—C3—C2 | 113.69 (11) | C20—C21—C30 | 120.79 (10) |
C3—O4—C5 | 113.93 (10) | N22—C21—C20 | 122.89 (11) |
O4—C5—C6 | 109.02 (11) | N22—C21—C30 | 116.32 (10) |
O7—C6—C5 | 115.01 (11) | C17—N22—C21 | 117.48 (10) |
C8—O7—C6 | 115.57 (10) | C24—C23—C19 | 121.01 (11) |
O7—C8—C9 | 115.53 (11) | C24—C23—C28 | 117.96 (11) |
O10—C9—C8 | 107.68 (10) | C28—C23—C19 | 121.01 (11) |
C35—O10—C9 | 118.22 (9) | C25—C24—C23 | 120.65 (12) |
O1—C11—C12 | 123.37 (11) | C24—C25—C26 | 121.29 (12) |
O1—C11—C16 | 116.35 (10) | C25—C26—C29 | 120.26 (13) |
C12—C11—C16 | 120.28 (11) | C27—C26—C25 | 118.03 (12) |
C13—C12—C11 | 120.08 (11) | C27—C26—C29 | 121.71 (13) |
C14—C13—C12 | 120.35 (11) | C26—C27—C28 | 121.18 (12) |
C13—C14—C15 | 119.34 (11) | C27—C28—C23 | 120.87 (12) |
C16—C15—C14 | 121.68 (11) | C31—C30—C21 | 121.75 (11) |
C11—C16—C17 | 122.26 (10) | C31—C30—C35 | 118.58 (11) |
C15—C16—C11 | 118.26 (11) | C35—C30—C21 | 119.67 (10) |
C15—C16—C17 | 119.43 (11) | C30—C31—C32 | 120.76 (12) |
C18—C17—C16 | 121.91 (10) | C33—C32—C31 | 120.00 (12) |
N22—C17—C16 | 115.01 (10) | C32—C33—C34 | 120.62 (12) |
N22—C17—C18 | 123.06 (11) | C33—C34—C35 | 119.34 (11) |
C17—C18—C19 | 119.54 (11) | O10—C35—C30 | 115.21 (10) |
C18—C19—C20 | 117.18 (11) | O10—C35—C34 | 124.11 (11) |
C18—C19—C23 | 121.50 (11) | C34—C35—C30 | 120.66 (11) |
Cg1, Cg2, Cg3 and Cg4 are the centroids of rings A (N22/C17–C21), C (C11–C16), B (C23–C28) and D (C30–C35), respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N22i | 0.99 | 2.55 | 3.4606 (15) | 152 |
C3—H3B···Cg2ii | 0.99 | 2.75 | 3.6182 (15) | 146 |
C12—H12···Cg3iii | 0.95 | 2.93 | 3.7281 (13) | 142 |
C25—H25···Cg4iv | 0.95 | 2.86 | 3.6987 (15) | 148 |
C27—H27···Cg1v | 0.95 | 2.99 | 3.7685 (14) | 140 |
C34—H34···Cg2i | 0.95 | 2.77 | 3.5912 (13) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1/2, y−1/2, −z+3/2. |
Cg1, Cg2, Cg3 and Cg4 are the centroids of rings A (N22/C17–C21), C (C11–C16), B (C23–C28) and D (C30–C35), respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N22i | 0.99 | 2.55 | 3.4606 (15) | 152 |
C3—H3B···Cg2ii | 0.99 | 2.75 | 3.6182 (15) | 146 |
C12—H12···Cg3iii | 0.95 | 2.93 | 3.7281 (13) | 142 |
C25—H25···Cg4iv | 0.95 | 2.86 | 3.6987 (15) | 148 |
C27—H27···Cg1v | 0.95 | 2.99 | 3.7685 (14) | 140 |
C34—H34···Cg2i | 0.95 | 2.77 | 3.5912 (13) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C30H29NO4 |
Mr | 467.54 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 10.0819 (4), 10.4531 (4), 23.6016 (9) |
β (°) | 100.607 (1) |
V (Å3) | 2444.80 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.14 × 0.12 × 0.12 |
Data collection | |
Diffractometer | D8 Quest Bruker CMOS |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.695, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 77012, 5825, 4706 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.099, 1.01 |
No. of reflections | 5825 |
No. of parameters | 317 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.19 |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXT2014 (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009).
Acknowledgements
This research is funded by the Vietnam National University, Hanoi (VNU), under project number QG.16.05.
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