Diethyl 4-(3-chloro­phen­yl)-2-methyl-6-phenyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

Ahamed, F.M.M.; Padusha, M.S.A.; Gunasekaran, B.

doi:10.1107/S2414314616001553

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160155

doi:10.1107/S2414314616001553

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Diethyl 4-(3-chlorophenyl)-2-methyl-6-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

F. M. Mashood Ahamed,^a M. Syed Ali Padusha ^a and B. Gunasekaran ^b ^*

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 December 2015; accepted 25 January 2016; online 28 January 2016)

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

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Chemical scheme

Structure description

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 studies in this area, we now report the synthesis and structure of the title compound, (I).

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 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)°.

Figure 1
The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

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).

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 2
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₄ClNO₄
M_r	425.89
Crystal system, space group	Triclinic, P $[\overline{1}]$
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 )
T_min, T_max	0.958, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15576, 4480, 3491
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25
Computer programs: APEX2 (Bruker, 2008 ), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1449762

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616001553/hb4010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616001553/hb4010Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616001553/hb4010Isup3.cml

checkCIF report

Experimental top

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%.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top

	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.

Diethyl 4-(3-chlorophenyl)-2-methyl-6-phenyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₄H₂₄ClNO₄	Z = 2
M_r = 425.89	F(000) = 448
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4480 independent reflections
Radiation source: fine-focus sealed tube	3491 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 0 pixels mm^-1	θ_max = 26.6°, θ_min = 1.6°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.958, T_max = 0.977	l = −16→16
15576 measured reflections

Refinement top

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(F_o²) + (0.0532P)² + 0.5427P] where P = (F_o² + 2F_c²)/3
4480 reflections	(Δ/σ)_max < 0.001
274 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₄H₂₄ClNO₄	γ = 91.275 (5)°
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	4480 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3491 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.977	R_int = 0.022
15576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
4480 reflections	Δρ_min = −0.25 e Å⁻³
274 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.958, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15576, 4480, 3491
R_int	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
Δρ_max, Δρ_min (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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