organic compounds
Diethyl 4-(3-chlorophenyl)-2-methyl-6-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
aPG and Research Dept of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu 620 020, India, and bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com
In the title compound, C24H24ClNO4, the dihydropyridine ring adopts a flattened boat conformation. The plane of the pyridine ring subtends dihedral angles of 74.54 (6) and 85.69 (5)° with those of the phenyl and chlorophenyl rings, respectively. The dihedral angle between the planes of the chlorophenyl and phenyl rings is 72.20 (7)°. In the crystal, molecules are linked into [100] C(6) chains by N—H⋯O hydrogen bonds. The chains are cross-linked by weak C—H⋯O interactions to generate a three-dimensional network.
Keywords: crystal structure; hydrogen bonds,.
CCDC reference: 1449762
Structure description
et al., 2011), anticancer (Srivastava & Pandeya 2011), anticonvulsant (Paronikyan et al., 2002) and antimycobacterial activities (Mamolo et al., 2004). As part of our studies in this area, we now report the synthesis and structure of the title compound, (I).
containing pyridine rings are associated with diverse pharmacological properties such as antimicrobial (PatelThe geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Steiger et al., 2014; Wang et al., 2013). The pyridine ring makes dihedral angles of 74.54 (6) and 85.69 (5)° with the phenyl and chlorophenyl rings, respectively. The dihedral angle between chlorophenyl and phenyl rings is 72.20 (7)°.
In the crystal, molecules are linked into [100] C(6) chains by N—H⋯O hydrogen bonds. The chains are cross-linked by weak C—H⋯O interactions to generate a three-dimensional network (Table 1 and Fig. 2).
Synthesis and crystallization
To an ethanolic solution of ammonium acetate (1.92 g, 0.025 M), ethyl benzoylacetate (4.32 ml, 0.025 M) was added followed by 3-chloro benzaldehyde (3.51 g, 0.025 M) and ethyl acetoacetate (3.18ml, 0.025 M). The reaction mixture was taken in a round-bottom flask and refluxed for 24 h at 80° C and allowed to cool. The turbid solution obtained was kept over a magnetic stirrer and stirred for four h. The precipitate obtained was filtered, dried and recrystallized using absolute ethanol to obtain yellow blocks with a melting point of 160° C and a yield of 70%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1449762
10.1107/S2414314616001553/hb4010sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616001553/hb4010Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616001553/hb4010Isup3.cml
To an ethanolic solution of ammonium acetate(1.92 g, 0.025 M), ethyl benzoylacetate (4.32 ml, 0.025 M) was added followed by 3-chloro benzaldehyde (3.51 g, 0.025 M) and ethyl acetoacetate (3.18 ml, 0.025 M). The reaction mixture was taken in a rund-bottom flask and refluxed for 24 h at 80° C and allowed to cool. The turbid solution obtained was kept over a magnetic stirrer and stirred for four hours. The precipitate obtained was filtered, dried and recrystallized using absolute ethanol to obtain yellow blocks with a melting point of 160° C and a yield of 70%.
Heterocyclic compounds containing pyridine rings are associated with diverse pharmacological properties such as antimicrobial (Patel et al., 2011), anticancer (Srivastava & Pandeya 2011) anticonvulsant (Paronikyan et al., 2002) and antimycobacterial activities (Mamolo et al., 2004). As part of our stuides in this area, we now report the synthesis and structure of the title compound.
The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Steiger et al., 2014; Wang et al., 2013). The pyridine ring makes a dihedral angles of 74.54 (6) and 85.69 (5)° with the phenyl and chlorophenyl rings, respectively. The dihedral angle between chlorophenyl and phenyl rings is 72.20 (7)°.
In the crystal, molecules are linked into [100] C(6) chains by N—H···O hydrogen bonds. The chains are cross-linked by weak C—H···O interactions to generate a three-dimensional network (Table 1 and Fig. 2).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. | |
Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. |
C24H24ClNO4 | Z = 2 |
Mr = 425.89 | F(000) = 448 |
Triclinic, P1 | Dx = 1.318 Mg m−3 |
a = 7.621 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.753 (5) Å | Cell parameters from 4480 reflections |
c = 13.138 (5) Å | θ = 1.6–26.6° |
α = 92.102 (5)° | µ = 0.21 mm−1 |
β = 93.806 (5)° | T = 295 K |
γ = 91.275 (5)° | Block, yellow |
V = 1073.2 (10) Å3 | 0.23 × 0.17 × 0.11 mm |
Bruker APEXII CCD diffractometer | 4480 independent reflections |
Radiation source: fine-focus sealed tube | 3491 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 0 pixels mm-1 | θmax = 26.6°, θmin = 1.6° |
ω and φ scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.958, Tmax = 0.977 | l = −16→16 |
15576 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.5427P] where P = (Fo2 + 2Fc2)/3 |
4480 reflections | (Δ/σ)max < 0.001 |
274 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C24H24ClNO4 | γ = 91.275 (5)° |
Mr = 425.89 | V = 1073.2 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.621 (5) Å | Mo Kα radiation |
b = 10.753 (5) Å | µ = 0.21 mm−1 |
c = 13.138 (5) Å | T = 295 K |
α = 92.102 (5)° | 0.23 × 0.17 × 0.11 mm |
β = 93.806 (5)° |
Bruker APEXII CCD diffractometer | 4480 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3491 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.977 | Rint = 0.022 |
15576 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.29 e Å−3 |
4480 reflections | Δρmin = −0.25 e Å−3 |
274 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5155 (3) | 0.40545 (18) | 0.16421 (16) | 0.0429 (4) | |
H1A | 0.4998 | 0.3671 | 0.0996 | 0.051* | |
C2 | 0.5597 (3) | 0.53110 (19) | 0.17448 (19) | 0.0537 (5) | |
H2 | 0.5705 | 0.5774 | 0.1167 | 0.064* | |
C3 | 0.5876 (3) | 0.58753 (18) | 0.2697 (2) | 0.0570 (6) | |
H3 | 0.6159 | 0.6721 | 0.2765 | 0.068* | |
C4 | 0.5737 (3) | 0.51907 (19) | 0.35468 (19) | 0.0550 (6) | |
H4 | 0.5964 | 0.5569 | 0.4192 | 0.066* | |
C5 | 0.5261 (3) | 0.39396 (18) | 0.34544 (16) | 0.0436 (4) | |
H5 | 0.5152 | 0.3483 | 0.4035 | 0.052* | |
C6 | 0.4948 (2) | 0.33704 (15) | 0.24965 (14) | 0.0322 (4) | |
C7 | 0.4397 (2) | 0.20311 (15) | 0.23494 (13) | 0.0307 (4) | |
C8 | 0.2751 (2) | 0.15345 (15) | 0.23497 (13) | 0.0311 (4) | |
C9 | 0.1176 (2) | 0.22663 (16) | 0.24928 (14) | 0.0354 (4) | |
C10 | 0.0044 (3) | 0.4246 (2) | 0.2929 (2) | 0.0683 (7) | |
H10A | −0.0696 | 0.3896 | 0.3425 | 0.082* | |
H10B | −0.0661 | 0.4326 | 0.2293 | 0.082* | |
C11 | 0.0763 (4) | 0.5464 (3) | 0.3303 (4) | 0.1272 (17) | |
H11A | 0.1455 | 0.5374 | 0.3932 | 0.191* | |
H11B | −0.0184 | 0.6016 | 0.3416 | 0.191* | |
H11C | 0.1489 | 0.5802 | 0.2805 | 0.191* | |
C12 | 0.2418 (2) | 0.01385 (14) | 0.21610 (13) | 0.0310 (4) | |
H12 | 0.1304 | 0.0021 | 0.1748 | 0.037* | |
C13 | 0.2234 (2) | −0.05196 (15) | 0.31574 (13) | 0.0316 (4) | |
C14 | 0.0581 (2) | −0.08508 (16) | 0.34641 (14) | 0.0354 (4) | |
H14 | −0.0423 | −0.0688 | 0.3054 | 0.042* | |
C15 | 0.0437 (2) | −0.14221 (16) | 0.43803 (15) | 0.0389 (4) | |
C16 | 0.1879 (3) | −0.16631 (19) | 0.50181 (16) | 0.0476 (5) | |
H16 | 0.1756 | −0.2034 | 0.5639 | 0.057* | |
C17 | 0.3521 (3) | −0.1338 (2) | 0.47086 (17) | 0.0497 (5) | |
H17 | 0.4518 | −0.1493 | 0.5127 | 0.060* | |
C18 | 0.3702 (2) | −0.07876 (18) | 0.37911 (15) | 0.0421 (4) | |
H18 | 0.4821 | −0.0592 | 0.3592 | 0.051* | |
C19 | 0.3864 (2) | −0.04154 (15) | 0.15517 (13) | 0.0316 (4) | |
C20 | 0.3488 (2) | −0.15654 (16) | 0.09419 (14) | 0.0384 (4) | |
C21 | 0.1295 (3) | −0.3022 (2) | 0.0290 (2) | 0.0740 (8) | |
H21A | 0.1847 | −0.3744 | 0.0581 | 0.089* | |
H21B | 0.1686 | −0.2933 | −0.0392 | 0.089* | |
C22 | −0.0614 (4) | −0.3180 (3) | 0.0247 (3) | 0.0959 (11) | |
H22A | −0.0985 | −0.3284 | 0.0924 | 0.144* | |
H22B | −0.0964 | −0.3903 | −0.0175 | 0.144* | |
H22C | −0.1148 | −0.2458 | −0.0035 | 0.144* | |
C23 | 0.5485 (2) | 0.01250 (15) | 0.15995 (13) | 0.0310 (4) | |
C24 | 0.7087 (2) | −0.03756 (18) | 0.11409 (15) | 0.0416 (4) | |
H24A | 0.7428 | −0.1123 | 0.1471 | 0.062* | |
H24B | 0.8030 | 0.0233 | 0.1233 | 0.062* | |
H24C | 0.6828 | −0.0558 | 0.0425 | 0.062* | |
N1 | 0.57631 (18) | 0.12722 (13) | 0.20987 (11) | 0.0336 (3) | |
H1 | 0.6827 | 0.1526 | 0.2261 | 0.040* | |
O1 | 0.15107 (17) | 0.34518 (12) | 0.27709 (14) | 0.0575 (4) | |
O2 | −0.03089 (16) | 0.18390 (12) | 0.23772 (13) | 0.0522 (4) | |
O3 | 0.17836 (19) | −0.19126 (13) | 0.09204 (13) | 0.0574 (4) | |
O4 | 0.4528 (2) | −0.21604 (13) | 0.04750 (12) | 0.0564 (4) | |
Cl1 | −0.16512 (7) | −0.18564 (5) | 0.47366 (5) | 0.05796 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0436 (10) | 0.0393 (10) | 0.0461 (11) | −0.0009 (8) | 0.0064 (8) | −0.0001 (8) |
C2 | 0.0526 (12) | 0.0374 (10) | 0.0728 (15) | −0.0013 (9) | 0.0114 (11) | 0.0135 (10) |
C3 | 0.0515 (12) | 0.0284 (9) | 0.0907 (18) | −0.0044 (8) | 0.0097 (12) | −0.0068 (11) |
C4 | 0.0566 (13) | 0.0428 (11) | 0.0636 (14) | −0.0034 (9) | 0.0037 (10) | −0.0215 (10) |
C5 | 0.0472 (11) | 0.0390 (10) | 0.0441 (11) | −0.0009 (8) | 0.0036 (9) | −0.0045 (8) |
C6 | 0.0238 (8) | 0.0297 (8) | 0.0434 (10) | 0.0017 (6) | 0.0049 (7) | −0.0023 (7) |
C7 | 0.0290 (8) | 0.0278 (8) | 0.0352 (9) | 0.0026 (6) | 0.0026 (7) | −0.0031 (7) |
C8 | 0.0284 (8) | 0.0270 (8) | 0.0377 (9) | 0.0018 (6) | 0.0031 (7) | −0.0022 (7) |
C9 | 0.0289 (8) | 0.0303 (8) | 0.0475 (11) | 0.0008 (7) | 0.0059 (7) | −0.0003 (7) |
C10 | 0.0391 (11) | 0.0388 (11) | 0.128 (2) | 0.0119 (9) | 0.0172 (13) | −0.0155 (13) |
C11 | 0.0606 (17) | 0.0581 (17) | 0.259 (5) | 0.0115 (14) | 0.015 (2) | −0.065 (2) |
C12 | 0.0255 (8) | 0.0268 (8) | 0.0401 (10) | 0.0006 (6) | 0.0003 (7) | −0.0030 (7) |
C13 | 0.0303 (8) | 0.0254 (8) | 0.0389 (10) | −0.0004 (6) | 0.0051 (7) | −0.0044 (7) |
C14 | 0.0294 (8) | 0.0324 (9) | 0.0438 (10) | −0.0015 (7) | 0.0017 (7) | −0.0039 (7) |
C15 | 0.0361 (9) | 0.0322 (9) | 0.0487 (11) | −0.0044 (7) | 0.0114 (8) | −0.0056 (8) |
C16 | 0.0517 (12) | 0.0473 (11) | 0.0447 (11) | −0.0029 (9) | 0.0068 (9) | 0.0084 (9) |
C17 | 0.0402 (10) | 0.0580 (12) | 0.0509 (12) | 0.0014 (9) | −0.0024 (9) | 0.0135 (10) |
C18 | 0.0302 (9) | 0.0469 (11) | 0.0496 (11) | −0.0008 (8) | 0.0032 (8) | 0.0064 (9) |
C19 | 0.0341 (8) | 0.0263 (8) | 0.0341 (9) | 0.0037 (7) | 0.0019 (7) | −0.0011 (7) |
C20 | 0.0427 (10) | 0.0312 (9) | 0.0408 (10) | 0.0011 (8) | 0.0014 (8) | −0.0020 (8) |
C21 | 0.0586 (14) | 0.0497 (13) | 0.110 (2) | −0.0095 (11) | 0.0022 (14) | −0.0384 (14) |
C22 | 0.0627 (16) | 0.0712 (18) | 0.148 (3) | −0.0094 (14) | −0.0013 (18) | −0.0498 (19) |
C23 | 0.0328 (8) | 0.0283 (8) | 0.0322 (9) | 0.0066 (6) | 0.0022 (7) | 0.0000 (7) |
C24 | 0.0352 (9) | 0.0406 (10) | 0.0490 (11) | 0.0076 (8) | 0.0059 (8) | −0.0063 (8) |
N1 | 0.0236 (7) | 0.0311 (7) | 0.0457 (9) | 0.0014 (5) | 0.0025 (6) | −0.0065 (6) |
O1 | 0.0303 (7) | 0.0326 (7) | 0.1100 (13) | 0.0042 (5) | 0.0156 (7) | −0.0153 (7) |
O2 | 0.0259 (6) | 0.0417 (7) | 0.0881 (11) | 0.0017 (5) | 0.0035 (6) | −0.0091 (7) |
O3 | 0.0468 (8) | 0.0430 (8) | 0.0802 (11) | −0.0074 (6) | 0.0055 (7) | −0.0257 (7) |
O4 | 0.0597 (9) | 0.0408 (8) | 0.0683 (10) | 0.0025 (7) | 0.0141 (8) | −0.0208 (7) |
Cl1 | 0.0443 (3) | 0.0612 (3) | 0.0697 (4) | −0.0131 (2) | 0.0221 (2) | −0.0033 (3) |
C1—C6 | 1.380 (3) | C13—C14 | 1.390 (2) |
C1—C2 | 1.385 (3) | C13—C18 | 1.392 (3) |
C1—H1A | 0.9300 | C14—C15 | 1.381 (3) |
C2—C3 | 1.372 (3) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.373 (3) |
C3—C4 | 1.368 (3) | C15—Cl1 | 1.747 (2) |
C3—H3 | 0.9300 | C16—C17 | 1.383 (3) |
C4—C5 | 1.384 (3) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—C18 | 1.376 (3) |
C5—C6 | 1.383 (3) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—C7 | 1.493 (2) | C19—C23 | 1.350 (2) |
C7—C8 | 1.353 (2) | C19—C20 | 1.461 (2) |
C7—N1 | 1.386 (2) | C20—O4 | 1.214 (2) |
C8—C9 | 1.469 (2) | C20—O3 | 1.341 (2) |
C8—C12 | 1.525 (2) | C21—O3 | 1.454 (2) |
C9—O2 | 1.210 (2) | C21—C22 | 1.458 (4) |
C9—O1 | 1.328 (2) | C21—H21A | 0.9700 |
C10—O1 | 1.443 (2) | C21—H21B | 0.9700 |
C10—C11 | 1.464 (3) | C22—H22A | 0.9600 |
C10—H10A | 0.9700 | C22—H22B | 0.9600 |
C10—H10B | 0.9700 | C22—H22C | 0.9600 |
C11—H11A | 0.9600 | C23—N1 | 1.381 (2) |
C11—H11B | 0.9600 | C23—C24 | 1.499 (2) |
C11—H11C | 0.9600 | C24—H24A | 0.9600 |
C12—C19 | 1.523 (2) | C24—H24B | 0.9600 |
C12—C13 | 1.524 (2) | C24—H24C | 0.9600 |
C12—H12 | 0.9800 | N1—H1 | 0.8600 |
C6—C1—C2 | 120.19 (19) | C15—C14—C13 | 119.76 (16) |
C6—C1—H1A | 119.9 | C15—C14—H14 | 120.1 |
C2—C1—H1A | 119.9 | C13—C14—H14 | 120.1 |
C3—C2—C1 | 120.2 (2) | C16—C15—C14 | 122.18 (17) |
C3—C2—H2 | 119.9 | C16—C15—Cl1 | 118.95 (16) |
C1—C2—H2 | 119.9 | C14—C15—Cl1 | 118.87 (14) |
C4—C3—C2 | 119.85 (19) | C15—C16—C17 | 117.91 (19) |
C4—C3—H3 | 120.1 | C15—C16—H16 | 121.0 |
C2—C3—H3 | 120.1 | C17—C16—H16 | 121.0 |
C3—C4—C5 | 120.5 (2) | C18—C17—C16 | 121.02 (18) |
C3—C4—H4 | 119.7 | C18—C17—H17 | 119.5 |
C5—C4—H4 | 119.7 | C16—C17—H17 | 119.5 |
C6—C5—C4 | 119.9 (2) | C17—C18—C13 | 120.86 (17) |
C6—C5—H5 | 120.1 | C17—C18—H18 | 119.6 |
C4—C5—H5 | 120.1 | C13—C18—H18 | 119.6 |
C1—C6—C5 | 119.33 (17) | C23—C19—C20 | 120.41 (16) |
C1—C6—C7 | 118.40 (16) | C23—C19—C12 | 120.59 (15) |
C5—C6—C7 | 122.26 (17) | C20—C19—C12 | 118.97 (15) |
C8—C7—N1 | 119.19 (15) | O4—C20—O3 | 121.31 (17) |
C8—C7—C6 | 127.54 (15) | O4—C20—C19 | 126.59 (17) |
N1—C7—C6 | 113.00 (14) | O3—C20—C19 | 112.08 (15) |
C7—C8—C9 | 124.08 (15) | O3—C21—C22 | 108.2 (2) |
C7—C8—C12 | 120.59 (14) | O3—C21—H21A | 110.1 |
C9—C8—C12 | 115.31 (14) | C22—C21—H21A | 110.1 |
O2—C9—O1 | 122.04 (16) | O3—C21—H21B | 110.1 |
O2—C9—C8 | 123.68 (16) | C22—C21—H21B | 110.1 |
O1—C9—C8 | 114.28 (14) | H21A—C21—H21B | 108.4 |
O1—C10—C11 | 107.45 (19) | C21—C22—H22A | 109.5 |
O1—C10—H10A | 110.2 | C21—C22—H22B | 109.5 |
C11—C10—H10A | 110.2 | H22A—C22—H22B | 109.5 |
O1—C10—H10B | 110.2 | C21—C22—H22C | 109.5 |
C11—C10—H10B | 110.2 | H22A—C22—H22C | 109.5 |
H10A—C10—H10B | 108.5 | H22B—C22—H22C | 109.5 |
C10—C11—H11A | 109.5 | C19—C23—N1 | 119.27 (15) |
C10—C11—H11B | 109.5 | C19—C23—C24 | 126.90 (16) |
H11A—C11—H11B | 109.5 | N1—C23—C24 | 113.82 (15) |
C10—C11—H11C | 109.5 | C23—C24—H24A | 109.5 |
H11A—C11—H11C | 109.5 | C23—C24—H24B | 109.5 |
H11B—C11—H11C | 109.5 | H24A—C24—H24B | 109.5 |
C19—C12—C13 | 111.77 (13) | C23—C24—H24C | 109.5 |
C19—C12—C8 | 110.17 (13) | H24A—C24—H24C | 109.5 |
C13—C12—C8 | 111.45 (14) | H24B—C24—H24C | 109.5 |
C19—C12—H12 | 107.8 | C23—N1—C7 | 122.66 (14) |
C13—C12—H12 | 107.8 | C23—N1—H1 | 118.7 |
C8—C12—H12 | 107.8 | C7—N1—H1 | 118.7 |
C14—C13—C18 | 118.24 (17) | C9—O1—C10 | 118.31 (15) |
C14—C13—C12 | 120.53 (15) | C20—O3—C21 | 115.18 (16) |
C18—C13—C12 | 121.22 (15) | ||
C6—C1—C2—C3 | 1.7 (3) | C13—C14—C15—C16 | 1.0 (3) |
C1—C2—C3—C4 | 0.7 (3) | C13—C14—C15—Cl1 | −178.77 (13) |
C2—C3—C4—C5 | −2.1 (3) | C14—C15—C16—C17 | −1.3 (3) |
C3—C4—C5—C6 | 1.0 (3) | Cl1—C15—C16—C17 | 178.49 (16) |
C2—C1—C6—C5 | −2.8 (3) | C15—C16—C17—C18 | 0.1 (3) |
C2—C1—C6—C7 | 177.45 (17) | C16—C17—C18—C13 | 1.3 (3) |
C4—C5—C6—C1 | 1.5 (3) | C14—C13—C18—C17 | −1.6 (3) |
C4—C5—C6—C7 | −178.78 (18) | C12—C13—C18—C17 | 177.41 (18) |
C1—C6—C7—C8 | −96.3 (2) | C13—C12—C19—C23 | −97.89 (18) |
C5—C6—C7—C8 | 83.9 (2) | C8—C12—C19—C23 | 26.6 (2) |
C1—C6—C7—N1 | 77.6 (2) | C13—C12—C19—C20 | 80.00 (19) |
C5—C6—C7—N1 | −102.10 (19) | C8—C12—C19—C20 | −155.52 (15) |
N1—C7—C8—C9 | −173.11 (16) | C23—C19—C20—O4 | 3.2 (3) |
C6—C7—C8—C9 | 0.5 (3) | C12—C19—C20—O4 | −174.65 (18) |
N1—C7—C8—C12 | 4.9 (3) | C23—C19—C20—O3 | −175.15 (16) |
C6—C7—C8—C12 | 178.51 (16) | C12—C19—C20—O3 | 7.0 (2) |
C7—C8—C9—O2 | 171.24 (19) | C20—C19—C23—N1 | 173.75 (15) |
C12—C8—C9—O2 | −6.8 (3) | C12—C19—C23—N1 | −8.4 (2) |
C7—C8—C9—O1 | −9.2 (3) | C20—C19—C23—C24 | −4.9 (3) |
C12—C8—C9—O1 | 172.68 (16) | C12—C19—C23—C24 | 172.92 (16) |
C7—C8—C12—C19 | −24.8 (2) | C19—C23—N1—C7 | −15.4 (2) |
C9—C8—C12—C19 | 153.40 (15) | C24—C23—N1—C7 | 163.49 (16) |
C7—C8—C12—C13 | 99.91 (18) | C8—C7—N1—C23 | 17.2 (3) |
C9—C8—C12—C13 | −81.93 (18) | C6—C7—N1—C23 | −157.34 (15) |
C19—C12—C13—C14 | −135.33 (16) | O2—C9—O1—C10 | −0.5 (3) |
C8—C12—C13—C14 | 100.91 (17) | C8—C9—O1—C10 | 179.9 (2) |
C19—C12—C13—C18 | 45.7 (2) | C11—C10—O1—C9 | 175.7 (3) |
C8—C12—C13—C18 | −78.08 (19) | O4—C20—O3—C21 | −1.1 (3) |
C18—C13—C14—C15 | 0.4 (2) | C19—C20—O3—C21 | 177.43 (19) |
C12—C13—C14—C15 | −178.58 (15) | C22—C21—O3—C20 | −173.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.20 | 3.037 (3) | 166 |
C24—H24B···O2i | 0.96 | 2.51 | 3.365 (3) | 148 |
C2—H2···O4ii | 0.93 | 2.59 | 3.330 (3) | 137 |
C1—H1A···O4iii | 0.93 | 2.53 | 3.412 (3) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.20 | 3.037 (3) | 166 |
C24—H24B···O2i | 0.96 | 2.51 | 3.365 (3) | 148 |
C2—H2···O4ii | 0.93 | 2.59 | 3.330 (3) | 137 |
C1—H1A···O4iii | 0.93 | 2.53 | 3.412 (3) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C24H24ClNO4 |
Mr | 425.89 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.621 (5), 10.753 (5), 13.138 (5) |
α, β, γ (°) | 92.102 (5), 93.806 (5), 91.275 (5) |
V (Å3) | 1073.2 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.23 × 0.17 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.958, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15576, 4480, 3491 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.630 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.02 |
No. of reflections | 4480 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.25 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
The authors thankful to the college management and the Principal for their support and the necessary facilities provided.
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