organic compounds
Diethyl 2,6-dimethyl-4-(naphthalen-1-yl)-1,4-dihydropyridine-3,5-dicarboxylate
aDepartment of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: noorsb@rediffmail.com
In the title compound, C23H25NO4, the 1,4-dihydropyridine ring adopts a flattened boat conformation. The naphthalene ring system forms a dihedral angle of 88.59 (6)° with the pyridine ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate an R12(6) ring motif and result in a zigzag chain along the b axis. Additional C—H⋯O hydrogen bonds form infinite chains along the c-axis direction.
Keywords: crystal structure; pyridine derivatives; hydrogen bonds; biological activity; Hantzsch reaction.
CCDC reference: 1477134
Structure description
1,4-Dihydropyridines (1,4-DHPs) are an important class of chemicals widely used as drugs or their precursors (Giorgi et al., 2010; Lavanya et al., 2011; Datar & Pratibha, 2012). 1,4-Dihydropyridine compounds are prescribed for the treatment of hypertension and heart defibrilation (Metcalf & Holt, 2000). Dihydropyridines (DHPs), in particular 4-aryl-substituted 1,4-dihydropyridines (Hantzsch esters), have been recognized as an important class of organic calcium channel modulators for the treatment of cardiovascular diseases (Zonouz et al., 2013). Herein, we report the of the title 4-aryl-substituted 1,4-dihydropyridine compound, (Fig. 1).
The naphthalene substituent at C4 is positioned axially and is inclined to the pyridine ring at a dihedral angle of 88.590 (6)°. The pyridine ring with the naphthalene substituent at the C4 atom is significantly puckered and adopts a flattened boat conformation with atoms N1 and C4 displaced by 0.1444 (3) and 0.322 (6) Å, respectively, from the mean plane of the other four atoms C5/C6/C2/C3. Both ethylcarboxylate substituents on the dihydropyridine ring adopt cis orientations of the carbonyl O atoms and the adjacent methyl groups with respect to the C2=C3 and C5=C6 double bonds, respectively. This contrasts with two of three methoxy-substituted 4-phenyl-2,6-dimethyl-1,4-dihydropyridine-3,6-dicarboxylate compounds (Metcalf & Holt, 2000) where there is one cis and one trans conformation. This may be due to the presence of a bulky naphthalene group in the title compound. The bond lengths and angles in the title compound are in good agreement with the corresponding values in closely related structures (Fun et al., 2012; Vrábel et al., 2005; Giorgi et al., 2010; Metcalf & Holt, 2000).
In the crystal, the O1 atom acts as a double-acceptor for the N1—H1⋯O1 and C7—H7⋯O1 hydrogen bonds (Table 1), generating an R21(6) ring motif and linking the molecules into zigzag chains running along the b axis (Fig. 2). C1—H1⋯O2 and C19—H19⋯O1 hydrogen bonds form infinite chains along the c-axis direction (Fig. 3).
Synthesis and crystallization
A mixture of naphthaldehyde (1 mmol), ethyl acetoacetate (2 mmol) and aqueous ammonia (1.5 mmol), was refluxed in dry ethanol (20 mmol) for 12 h. The progress of the reaction was monitored by TLC. After confirming that the reaction was complete, the reaction mixture was cooled to room temperature and allowed to stand for two days to allow the formation of a solid. The resulting solid product was washed with methanol and recrystallized from ethanol solution to yield single crystals suitable for X-ray diffraction studies (Yield: 78%; m.p. 192–194°C). The
of this compound was indeterminate in the present experiment.Refinement
Crystal data, data collection and structure . The compound, crystallizes in a non-centric monoclinic with one molecule in the but the cannot be determined reliably by of the because of insufficient effects.
details are summarized in Table 2Structural data
CCDC reference: 1477134
10.1107/S2414314616007227/sj4021sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007227/sj4021Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616007227/sj4021Isup3.cml
A mixture of naphthaldehyde (1 mmol), ethyl acetoacetate (2 mmol) and aqueous ammonia (1.5 mmol), was refluxed in dry ethanol (20 mmol) for 12 h. The progress of the reaction was monitored by TLC. After confirming that the reaction was complete, the reaction mixture was cooled to room temperature and allowed to stand for 2 days to allow the formation of a solid. The resulting solid product was washed with methanol and recrystallized from ethanol to yield single crystals suitable for X-ray diffraction studies (Yield: 78% ; m.p.192—194°C).
A mixture of naphthaldehyde (1 mmol), ethyl acetoacetate (2 mmol) and aqueous ammonia (1.5 mmol), was refluxed in dry ethanol (20 mmol) for 12 h. The progress of the reaction was monitored by TLC. After confirming that the reaction was complete, the reaction mixture was cooled to room temperature and allowed to stand for two days to allow the formation of a solid. The resulting solid product was washed with methanol and recrystallized from ethanol to yield single crystals suitable for X-ray diffraction studies (Yield: 78% ; m.p. 192–194°C).
Crystal data, data collection and structure
details are summarized in Table 2. The compound, crystallizes in a non-centric monoclinic with one molecule in the but the cannot be determined reliably by of the because of insufficient effects.1,4-Dihydropyridines (1,4-DHPs) are an important class of chemicals widely used as drugs or their precursors (Giorgi et al., 2010; Lavanya et al., 2011; Datar & Pratibha, 2012). 1,4-Dihydropyridine compounds are prescribed for the treatment of hypertension and heart defibrilation (Metcalf & Holt, 2000). Dihydropyridines (DHPs), in particular 4-aryl-substituted 1,4-dihydropyridines (Hantzsch esters), have been recognized as an important class of organic calcium channel modulators for the treatment of cardiovascular diseases (Zonouz et al., 2013). Herein, we report the
of the title 4-aryl-substituted 1,4-dihydropyridine compound, (Fig. 1).The naphthalene substituent at C4 is positioned axially and is inclined to the pyridine ring at a dihedral angle of 88.590 (6)°. The pyridine ring with the naphthalene substituent at the C4 atom is significantly puckered and adopts a flattened boat conformation with atoms N1 and C4 displaced by 0.1444 (3) and 0.322 (6) Å, respectively, from the mean plane of the other four atoms C5/C6/C2/C3. Both ethylcarboxylate substituents on the dihydropyridine ring adopt cis orientations of the carbonyl O atoms and the adjacent methyl groups with respect to the C2═C3 and C5═C6 double bonds, respectively. This contrasts with two of three methoxy-substituted 4-phenyl-2,6-dimethyl-1,4-dihydropyridine-3,6-dicarboxylate compounds (Metcalf & Holt, 2000) where there is one cis and one conformation. This may be due to the presence of a bulky naphthalene group in the title compound. The bond lengths and angles in the title compound are in good agreement with the corresponding values in closely related structures (Fun et al., 2012; Vrábel et al., 2005; Giorgi et al., 2010; Metcalf & Holt, 2000).
In the crystal, the O1 atom acts as a bifurcated acceptor for the N1—H1···O1 and C7—H7···O1 hydrogen bonds (Table 1), generating an R12(6) ring motif and linking the molecules into zigzag chains running along the b axis (Fig. 2). C1—H1···O2 and C19—H19···O1 hydrogen bonds form infinite chains along the c-axis direction (Fig. 3).
Data collection: SMART (Bruker, 1998); cell
SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. | |
Fig. 2. Unit-cell packing of the title compound showing C—H···O and N—H···O interactions as dashed lines. H atoms not involved in hydrogen bonding have been excluded. | |
Fig. 3. Unit-cell packing of the title compound showing C—H···O interactions as dashed lines. H-atoms not involved in hydrogen bonding have been omitted. |
C23H25NO4 | F(000) = 404 |
Mr = 379.44 | Dx = 1.312 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3319 reflections |
a = 8.7072 (17) Å | θ = 2.4–25.0° |
b = 9.8740 (19) Å | µ = 0.09 mm−1 |
c = 11.221 (2) Å | T = 100 K |
β = 95.307 (6)° | Block, colorless |
V = 960.6 (3) Å3 | 0.18 × 0.16 × 0.16 mm |
Z = 2 |
Bruker SMART APEX CCD diffractometer | 3319 independent reflections |
Radiation source: fine-focus sealed tube | 3046 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −10→10 |
Tmin = 0.984, Tmax = 0.986 | k = −11→11 |
7663 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0552P)2 + 0.5392P] where P = (Fo2 + 2Fc2)/3 |
3319 reflections | (Δ/σ)max = 0.006 |
257 parameters | Δρmax = 0.30 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
C23H25NO4 | V = 960.6 (3) Å3 |
Mr = 379.44 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.7072 (17) Å | µ = 0.09 mm−1 |
b = 9.8740 (19) Å | T = 100 K |
c = 11.221 (2) Å | 0.18 × 0.16 × 0.16 mm |
β = 95.307 (6)° |
Bruker SMART APEX CCD diffractometer | 3319 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 3046 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.986 | Rint = 0.048 |
7663 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 1 restraint |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
3319 reflections | Δρmin = −0.27 e Å−3 |
257 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0444 (2) | 0.6473 (2) | 0.85079 (17) | 0.0229 (5) | |
O3 | 0.6369 (2) | 0.1373 (2) | 0.9159 (2) | 0.0363 (6) | |
O2 | 0.2555 (2) | 0.6312 (2) | 0.75134 (16) | 0.0206 (4) | |
O4 | 0.6092 (2) | 0.3009 (2) | 0.77744 (16) | 0.0216 (5) | |
C18 | 0.1941 (3) | 0.2709 (3) | 0.4733 (2) | 0.0223 (6) | |
C6 | 0.3320 (3) | 0.2149 (3) | 0.9818 (2) | 0.0165 (6) | |
C11 | 0.5595 (3) | 0.2253 (3) | 0.8650 (2) | 0.0180 (6) | |
N1 | 0.1949 (3) | 0.2706 (2) | 1.00885 (18) | 0.0167 (5) | |
H1 | 0.1399 | 0.2262 | 1.0580 | 0.020* | |
C5 | 0.4022 (3) | 0.2669 (3) | 0.8886 (2) | 0.0159 (6) | |
C23 | 0.2732 (3) | 0.3409 (3) | 0.5723 (3) | 0.0200 (6) | |
C15 | 0.1469 (3) | 0.1912 (3) | 0.7039 (2) | 0.0170 (6) | |
H15 | 0.1301 | 0.1621 | 0.7823 | 0.020* | |
C4 | 0.3184 (3) | 0.3685 (3) | 0.8039 (2) | 0.0161 (6) | |
H4 | 0.3960 | 0.4350 | 0.7790 | 0.019* | |
C2 | 0.1386 (3) | 0.3929 (3) | 0.9629 (2) | 0.0152 (6) | |
C14 | 0.2448 (3) | 0.2979 (3) | 0.6911 (2) | 0.0168 (6) | |
C19 | 0.2202 (4) | 0.3115 (3) | 0.3546 (3) | 0.0266 (7) | |
H19 | 0.1682 | 0.2658 | 0.2881 | 0.032* | |
C16 | 0.0703 (3) | 0.1230 (3) | 0.6056 (2) | 0.0221 (6) | |
H16 | 0.0037 | 0.0491 | 0.6177 | 0.026* | |
C8 | 0.1561 (3) | 0.5826 (3) | 0.8255 (2) | 0.0159 (6) | |
C1 | 0.3898 (3) | 0.1038 (3) | 1.0646 (2) | 0.0220 (6) | |
H1A | 0.4127 | 0.0237 | 1.0178 | 0.033* | |
H1B | 0.3109 | 0.0811 | 1.1182 | 0.033* | |
H1C | 0.4839 | 0.1337 | 1.1120 | 0.033* | |
C17 | 0.0929 (3) | 0.1642 (3) | 0.4929 (3) | 0.0235 (7) | |
H17 | 0.0392 | 0.1201 | 0.4263 | 0.028* | |
C7 | 0.0198 (3) | 0.4559 (3) | 1.0338 (2) | 0.0223 (6) | |
H7A | 0.0550 | 0.5458 | 1.0614 | 0.033* | |
H7B | 0.0044 | 0.3987 | 1.1031 | 0.033* | |
H7C | −0.0778 | 0.4645 | 0.9834 | 0.033* | |
C3 | 0.1992 (3) | 0.4460 (3) | 0.8674 (2) | 0.0167 (6) | |
C9 | 0.2391 (4) | 0.7720 (3) | 0.7145 (3) | 0.0269 (7) | |
H9A | 0.1285 | 0.7966 | 0.7048 | 0.032* | |
H9B | 0.2814 | 0.7843 | 0.6362 | 0.032* | |
C12 | 0.7675 (3) | 0.2790 (3) | 0.7500 (3) | 0.0241 (7) | |
H12A | 0.7793 | 0.1872 | 0.7166 | 0.029* | |
H12B | 0.8395 | 0.2884 | 0.8231 | 0.029* | |
C22 | 0.3751 (3) | 0.4470 (3) | 0.5484 (3) | 0.0231 (7) | |
H22 | 0.4292 | 0.4943 | 0.6130 | 0.028* | |
C13 | 0.8000 (4) | 0.3842 (4) | 0.6602 (3) | 0.0344 (8) | |
H13A | 0.7254 | 0.3758 | 0.5896 | 0.052* | |
H13B | 0.9046 | 0.3716 | 0.6366 | 0.052* | |
H13C | 0.7913 | 0.4744 | 0.6955 | 0.052* | |
C21 | 0.3965 (4) | 0.4823 (4) | 0.4328 (3) | 0.0299 (8) | |
H21 | 0.4655 | 0.5536 | 0.4182 | 0.036* | |
C20 | 0.3175 (4) | 0.4139 (4) | 0.3359 (3) | 0.0304 (8) | |
H20 | 0.3328 | 0.4401 | 0.2563 | 0.036* | |
C10 | 0.3226 (4) | 0.8625 (3) | 0.8053 (3) | 0.0317 (8) | |
H10A | 0.2740 | 0.8570 | 0.8805 | 0.047* | |
H10B | 0.3180 | 0.9560 | 0.7760 | 0.047* | |
H10C | 0.4305 | 0.8338 | 0.8189 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0252 (11) | 0.0204 (11) | 0.0234 (10) | 0.0072 (9) | 0.0043 (8) | 0.0025 (9) |
O3 | 0.0269 (12) | 0.0407 (14) | 0.0427 (13) | 0.0166 (11) | 0.0096 (10) | 0.0209 (12) |
O2 | 0.0248 (10) | 0.0155 (10) | 0.0224 (10) | 0.0042 (9) | 0.0065 (8) | 0.0050 (8) |
O4 | 0.0167 (9) | 0.0236 (11) | 0.0252 (10) | 0.0042 (9) | 0.0053 (8) | 0.0062 (9) |
C18 | 0.0204 (14) | 0.0267 (16) | 0.0197 (13) | 0.0118 (14) | 0.0005 (11) | −0.0056 (13) |
C6 | 0.0155 (14) | 0.0156 (14) | 0.0176 (14) | −0.0034 (12) | −0.0024 (11) | −0.0020 (11) |
C11 | 0.0203 (14) | 0.0169 (15) | 0.0166 (13) | −0.0024 (12) | −0.0003 (11) | −0.0008 (12) |
N1 | 0.0174 (12) | 0.0154 (12) | 0.0177 (11) | −0.0014 (10) | 0.0044 (9) | 0.0027 (10) |
C5 | 0.0175 (13) | 0.0136 (14) | 0.0156 (12) | 0.0005 (12) | −0.0032 (10) | −0.0017 (11) |
C23 | 0.0198 (14) | 0.0215 (16) | 0.0188 (14) | 0.0077 (12) | 0.0017 (11) | −0.0011 (12) |
C15 | 0.0164 (14) | 0.0171 (15) | 0.0179 (14) | 0.0035 (12) | 0.0033 (11) | 0.0004 (11) |
C4 | 0.0154 (13) | 0.0157 (14) | 0.0174 (13) | −0.0022 (11) | 0.0025 (11) | 0.0011 (12) |
C2 | 0.0163 (13) | 0.0120 (14) | 0.0171 (13) | −0.0052 (12) | 0.0005 (10) | −0.0024 (11) |
C14 | 0.0156 (13) | 0.0139 (14) | 0.0208 (13) | 0.0077 (12) | 0.0009 (10) | 0.0009 (12) |
C19 | 0.0294 (17) | 0.0312 (18) | 0.0184 (14) | 0.0082 (15) | −0.0016 (12) | −0.0014 (13) |
C16 | 0.0193 (14) | 0.0185 (16) | 0.0281 (15) | 0.0011 (13) | 0.0005 (12) | −0.0059 (13) |
C8 | 0.0183 (14) | 0.0172 (14) | 0.0120 (12) | −0.0022 (13) | 0.0002 (10) | −0.0017 (11) |
C1 | 0.0215 (14) | 0.0218 (16) | 0.0224 (14) | 0.0017 (13) | −0.0001 (11) | 0.0029 (13) |
C17 | 0.0200 (15) | 0.0242 (16) | 0.0247 (15) | 0.0053 (13) | −0.0062 (12) | −0.0083 (13) |
C7 | 0.0230 (15) | 0.0211 (16) | 0.0235 (14) | −0.0005 (13) | 0.0057 (12) | −0.0005 (13) |
C3 | 0.0156 (13) | 0.0157 (14) | 0.0183 (13) | −0.0028 (12) | −0.0021 (11) | −0.0042 (12) |
C9 | 0.0329 (17) | 0.0193 (15) | 0.0292 (15) | 0.0031 (14) | 0.0068 (13) | 0.0078 (14) |
C12 | 0.0188 (14) | 0.0238 (16) | 0.0308 (15) | 0.0024 (14) | 0.0080 (12) | −0.0023 (14) |
C22 | 0.0212 (15) | 0.0238 (17) | 0.0245 (14) | 0.0033 (13) | 0.0027 (12) | 0.0011 (13) |
C13 | 0.0286 (17) | 0.0296 (19) | 0.047 (2) | 0.0078 (16) | 0.0163 (15) | 0.0084 (17) |
C21 | 0.0305 (18) | 0.0326 (18) | 0.0274 (16) | −0.0009 (15) | 0.0071 (14) | 0.0040 (14) |
C20 | 0.0335 (17) | 0.041 (2) | 0.0170 (15) | 0.0142 (16) | 0.0065 (12) | 0.0047 (14) |
C10 | 0.0250 (16) | 0.0201 (16) | 0.050 (2) | 0.0036 (13) | 0.0044 (15) | 0.0081 (15) |
O1—C8 | 1.219 (3) | C16—C17 | 1.359 (4) |
O3—C11 | 1.210 (4) | C16—H16 | 0.9500 |
O2—C8 | 1.344 (3) | C8—C3 | 1.466 (4) |
O2—C9 | 1.454 (4) | C1—H1A | 0.9800 |
O4—C11 | 1.338 (3) | C1—H1B | 0.9800 |
O4—C12 | 1.457 (3) | C1—H1C | 0.9800 |
C18—C17 | 1.404 (5) | C17—H17 | 0.9500 |
C18—C19 | 1.428 (4) | C7—H7A | 0.9800 |
C18—C23 | 1.430 (4) | C7—H7B | 0.9800 |
C6—C5 | 1.360 (4) | C7—H7C | 0.9800 |
C6—N1 | 1.373 (4) | C9—C10 | 1.492 (4) |
C6—C1 | 1.495 (4) | C9—H9A | 0.9900 |
C11—C5 | 1.477 (4) | C9—H9B | 0.9900 |
N1—C2 | 1.384 (4) | C12—C13 | 1.492 (5) |
N1—H1 | 0.8800 | C12—H12A | 0.9900 |
C5—C4 | 1.521 (4) | C12—H12B | 0.9900 |
C23—C22 | 1.414 (4) | C22—C21 | 1.372 (4) |
C23—C14 | 1.442 (4) | C22—H22 | 0.9500 |
C15—C14 | 1.371 (4) | C13—H13A | 0.9800 |
C15—C16 | 1.407 (4) | C13—H13B | 0.9800 |
C15—H15 | 0.9500 | C13—H13C | 0.9800 |
C4—C3 | 1.519 (4) | C21—C20 | 1.405 (5) |
C4—C14 | 1.533 (4) | C21—H21 | 0.9500 |
C4—H4 | 1.0000 | C20—H20 | 0.9500 |
C2—C3 | 1.344 (4) | C10—H10A | 0.9800 |
C2—C7 | 1.497 (4) | C10—H10B | 0.9800 |
C19—C20 | 1.349 (5) | C10—H10C | 0.9800 |
C19—H19 | 0.9500 | ||
C8—O2—C9 | 117.8 (2) | H1A—C1—H1C | 109.5 |
C11—O4—C12 | 116.7 (2) | H1B—C1—H1C | 109.5 |
C17—C18—C19 | 120.9 (3) | C16—C17—C18 | 121.2 (3) |
C17—C18—C23 | 120.3 (3) | C16—C17—H17 | 119.4 |
C19—C18—C23 | 118.8 (3) | C18—C17—H17 | 119.4 |
C5—C6—N1 | 118.7 (3) | C2—C7—H7A | 109.5 |
C5—C6—C1 | 127.2 (3) | C2—C7—H7B | 109.5 |
N1—C6—C1 | 114.0 (2) | H7A—C7—H7B | 109.5 |
O3—C11—O4 | 122.9 (3) | C2—C7—H7C | 109.5 |
O3—C11—C5 | 126.9 (3) | H7A—C7—H7C | 109.5 |
O4—C11—C5 | 110.2 (2) | H7B—C7—H7C | 109.5 |
C6—N1—C2 | 123.5 (2) | C2—C3—C8 | 120.5 (2) |
C6—N1—H1 | 118.2 | C2—C3—C4 | 120.9 (3) |
C2—N1—H1 | 118.2 | C8—C3—C4 | 118.6 (2) |
C6—C5—C11 | 121.5 (3) | O2—C9—C10 | 110.5 (2) |
C6—C5—C4 | 120.4 (2) | O2—C9—H9A | 109.6 |
C11—C5—C4 | 118.1 (2) | C10—C9—H9A | 109.6 |
C22—C23—C18 | 118.4 (3) | O2—C9—H9B | 109.6 |
C22—C23—C14 | 123.9 (3) | C10—C9—H9B | 109.6 |
C18—C23—C14 | 117.7 (3) | H9A—C9—H9B | 108.1 |
C14—C15—C16 | 122.7 (3) | O4—C12—C13 | 106.4 (2) |
C14—C15—H15 | 118.7 | O4—C12—H12A | 110.5 |
C16—C15—H15 | 118.7 | C13—C12—H12A | 110.5 |
C3—C4—C5 | 110.4 (2) | O4—C12—H12B | 110.5 |
C3—C4—C14 | 111.4 (2) | C13—C12—H12B | 110.5 |
C5—C4—C14 | 110.9 (2) | H12A—C12—H12B | 108.6 |
C3—C4—H4 | 108.0 | C21—C22—C23 | 120.7 (3) |
C5—C4—H4 | 108.0 | C21—C22—H22 | 119.7 |
C14—C4—H4 | 108.0 | C23—C22—H22 | 119.7 |
C3—C2—N1 | 119.0 (2) | C12—C13—H13A | 109.5 |
C3—C2—C7 | 127.1 (3) | C12—C13—H13B | 109.5 |
N1—C2—C7 | 113.8 (2) | H13A—C13—H13B | 109.5 |
C15—C14—C23 | 119.0 (2) | C12—C13—H13C | 109.5 |
C15—C14—C4 | 118.7 (2) | H13A—C13—H13C | 109.5 |
C23—C14—C4 | 122.3 (2) | H13B—C13—H13C | 109.5 |
C20—C19—C18 | 120.8 (3) | C22—C21—C20 | 120.7 (3) |
C20—C19—H19 | 119.6 | C22—C21—H21 | 119.7 |
C18—C19—H19 | 119.6 | C20—C21—H21 | 119.7 |
C17—C16—C15 | 119.2 (3) | C19—C20—C21 | 120.6 (3) |
C17—C16—H16 | 120.4 | C19—C20—H20 | 119.7 |
C15—C16—H16 | 120.4 | C21—C20—H20 | 119.7 |
O1—C8—O2 | 122.1 (3) | C9—C10—H10A | 109.5 |
O1—C8—C3 | 126.4 (2) | C9—C10—H10B | 109.5 |
O2—C8—C3 | 111.5 (2) | H10A—C10—H10B | 109.5 |
C6—C1—H1A | 109.5 | C9—C10—H10C | 109.5 |
C6—C1—H1B | 109.5 | H10A—C10—H10C | 109.5 |
H1A—C1—H1B | 109.5 | H10B—C10—H10C | 109.5 |
C6—C1—H1C | 109.5 | ||
C12—O4—C11—O3 | −3.9 (4) | C3—C4—C14—C23 | 110.4 (3) |
C12—O4—C11—C5 | 175.4 (2) | C5—C4—C14—C23 | −126.3 (3) |
C5—C6—N1—C2 | −13.3 (4) | C17—C18—C19—C20 | −180.0 (3) |
C1—C6—N1—C2 | 164.6 (2) | C23—C18—C19—C20 | 0.0 (4) |
N1—C6—C5—C11 | 171.3 (2) | C14—C15—C16—C17 | −0.3 (4) |
C1—C6—C5—C11 | −6.2 (4) | C9—O2—C8—O1 | 8.6 (4) |
N1—C6—C5—C4 | −9.9 (4) | C9—O2—C8—C3 | −172.3 (2) |
C1—C6—C5—C4 | 172.6 (3) | C15—C16—C17—C18 | 1.8 (4) |
O3—C11—C5—C6 | 6.1 (5) | C19—C18—C17—C16 | 178.5 (3) |
O4—C11—C5—C6 | −173.2 (2) | C23—C18—C17—C16 | −1.6 (4) |
O3—C11—C5—C4 | −172.8 (3) | N1—C2—C3—C8 | −172.5 (2) |
O4—C11—C5—C4 | 7.9 (3) | C7—C2—C3—C8 | 3.1 (4) |
C17—C18—C23—C22 | 179.5 (3) | N1—C2—C3—C4 | 5.0 (4) |
C19—C18—C23—C22 | −0.5 (4) | C7—C2—C3—C4 | −179.4 (3) |
C17—C18—C23—C14 | 0.0 (4) | O1—C8—C3—C2 | −17.1 (4) |
C19—C18—C23—C14 | 179.9 (3) | O2—C8—C3—C2 | 163.9 (2) |
C6—C5—C4—C3 | 26.8 (3) | O1—C8—C3—C4 | 165.3 (2) |
C11—C5—C4—C3 | −154.3 (2) | O2—C8—C3—C4 | −13.7 (3) |
C6—C5—C4—C14 | −97.1 (3) | C5—C4—C3—C2 | −24.4 (3) |
C11—C5—C4—C14 | 81.8 (3) | C14—C4—C3—C2 | 99.2 (3) |
C6—N1—C2—C3 | 15.9 (4) | C5—C4—C3—C8 | 153.2 (2) |
C6—N1—C2—C7 | −160.3 (2) | C14—C4—C3—C8 | −83.2 (3) |
C16—C15—C14—C23 | −1.2 (4) | C8—O2—C9—C10 | 85.1 (3) |
C16—C15—C14—C4 | 178.0 (3) | C11—O4—C12—C13 | −173.9 (3) |
C22—C23—C14—C15 | −178.1 (3) | C18—C23—C22—C21 | 0.4 (4) |
C18—C23—C14—C15 | 1.4 (4) | C14—C23—C22—C21 | 179.9 (3) |
C22—C23—C14—C4 | 2.7 (4) | C23—C22—C21—C20 | 0.1 (5) |
C18—C23—C14—C4 | −177.8 (2) | C18—C19—C20—C21 | 0.5 (5) |
C3—C4—C14—C15 | −68.8 (3) | C22—C21—C20—C19 | −0.6 (5) |
C5—C4—C14—C15 | 54.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 2.13 | 2.985 (3) | 164 |
C7—H7B···O1i | 0.98 | 2.58 | 3.378 (4) | 138 |
C19—H19···O1ii | 0.95 | 2.59 | 3.503 (4) | 161 |
C1—H1C···O2iii | 0.98 | 2.62 | 3.563 (3) | 161 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 2.129 | 2.985 (3) | 164 |
C7—H7B···O1i | 0.98 | 2.579 | 3.378 (4) | 138 |
C19—H19···O1ii | 0.95 | 2.587 | 3.503 (4) | 161 |
C1—H1C···O2iii | 0.98 | 2.619 | 3.563 (3) | 161 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C23H25NO4 |
Mr | 379.44 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 8.7072 (17), 9.8740 (19), 11.221 (2) |
β (°) | 95.307 (6) |
V (Å3) | 960.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.18 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.984, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7663, 3319, 3046 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.123, 1.05 |
No. of reflections | 3319 |
No. of parameters | 257 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.27 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 2012).
Acknowledgements
NLP is thankful to the University Grants Commission (UGC), India, for a UGC–JRF.
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