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

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

doi:10.1107/S2414314619016444

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 12| December 2019| x191644

https://doi.org/10.1107/S2414314619016444

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

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

^aPG & Research Department of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli-620 020, Tamilnadu, India, and ^bDepartment of Physics & Nano Technology, SRM Institute of Science and Technology, 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 22 November 2019; accepted 6 December 2019; online 10 December 2019)

In the title compound, C₂₉H₂₆ClNO₄, the dihydropyridine ring adopts a shallow boat conformation. The mean plane of the dihydropyridine ring (all atoms) subtends dihedral angles of 66.54 (1), 73.71 (1) and 79.47 (1)° with the two phenyl rings and the chlorophenyl ring, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into [001] chains.

Keywords: crystal structure; dihydropyridine; dicarboxylate.

CCDC reference: 1970514

Structure description

The geometric parameters of the title molecule (Fig. 1) agree well with those of reported similar structures (Wang et al., 2013 ; Ahamed et al., 2016 ). The dihydropyridine ring adopts a flattened boat conformation: atoms N1 and C12 are displaced out of the C7/C8/C19/C23 plane (r.m.s. deviation = 0.019 Å) by 0.124 (1) and 0.220 (2) Å, respectively. The mean plane of the pyridine ring (all atoms) subtends dihedral angles of 66.54 (1), 73.71 (1) and 79.47 (1)° with the 2- and 6-phenyl rings and the chlorophenyl ring, respectively. In the crystal, N—H⋯O hydrogen bonds (Fig. 2, Table 1) link the molecules into [001] chains.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.86	2.10	2.910 (2)	158
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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

Figure 2
The packing viewed down [100]. Hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

To an ethanolic solution of ammonium acetate (7.7 g, 0.1 mol), was added ethyl benzoylacetate (17.3 ml, 0.1 mol) followed by 3-chloro benzaldehyde (14 g, 0.1 mol). The reaction mixture was refluxed for 8 h and the turbid solution obtained was stirred for 10 min. The product separated out was washed, filtered and recrystallized from ethanol solution as yellow blocks (m.p. = 144°C, yield = 98%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₉H₂₆ClNO₄
M_r	487.96
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.519 (5), 22.059 (5), 11.246 (5)
β (°)	97.867 (5)
V (Å³)	2584.9 (18)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.968, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	24505, 6384, 3478
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.192, 1.06
No. of reflections	6384
No. of parameters	318
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2008 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1970514

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619016444/hb4329sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619016444/hb4329Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619016444/hb4329Isup3.cml

checkCIF report

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: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

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

Crystal data top

C₂₉H₂₆ClNO₄	F(000) = 1024
M_r = 487.96	D_x = 1.254 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.519 (5) Å	Cell parameters from 6384 reflections
b = 22.059 (5) Å	θ = 1.9–28.4°
c = 11.246 (5) Å	µ = 0.18 mm⁻¹
β = 97.867 (5)°	T = 295 K
V = 2584.9 (18) Å³	Block, yellow
Z = 4	0.20 × 0.15 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3478 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.029
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 28.4°, θ_min = 1.9°
T_min = 0.968, T_max = 0.975	h = −14→13
24505 measured reflections	k = −29→22
6384 independent reflections	l = −10→14

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.0826P)² + 0.5988P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
6384 reflections	Δρ_max = 0.28 e Å⁻³
318 parameters	Δρ_min = −0.40 e Å⁻³

Special details top

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.

Refinement. The H atoms were positioned geometrically (N—H = 0.86, C—H = 0.93–0.98 Å) and refined as riding atoms with U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(methyl carrier).

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

	x	y	z	U_iso*/U_eq
C1	0.3290 (2)	0.12025 (10)	0.47589 (19)	0.0522 (5)
H1	0.364970	0.156592	0.455041	0.063*
C2	0.4059 (2)	0.07648 (12)	0.5367 (2)	0.0707 (7)
H2	0.493445	0.083358	0.556614	0.085*
C3	0.3535 (3)	0.02293 (13)	0.5679 (2)	0.0757 (8)
H3	0.405875	−0.006916	0.607098	0.091*
C4	0.2245 (3)	0.01329 (11)	0.5414 (2)	0.0722 (7)
H4	0.188850	−0.022728	0.564405	0.087*
C5	0.1469 (2)	0.05674 (10)	0.4807 (2)	0.0582 (6)
H5	0.059071	0.049997	0.463143	0.070*
C6	0.19914 (19)	0.11043 (9)	0.44583 (17)	0.0428 (5)
C7	0.11605 (18)	0.15741 (9)	0.37990 (17)	0.0420 (5)
C8	0.0443 (2)	0.15097 (9)	0.27198 (18)	0.0463 (5)
C9	0.0366 (2)	0.09426 (11)	0.2012 (2)	0.0582 (6)
C10	0.1382 (3)	0.00161 (12)	0.1628 (3)	0.0837 (9)
H10A	0.114087	0.004609	0.076599	0.100*
H10B	0.075277	−0.023292	0.195352	0.100*
C11	0.2675 (4)	−0.02572 (15)	0.1905 (4)	0.1229 (14)
H11A	0.327992	−0.002317	0.152983	0.184*
H11B	0.265646	−0.066509	0.160525	0.184*
H11C	0.292792	−0.026027	0.275777	0.184*
C12	−0.0380 (2)	0.20264 (10)	0.21539 (18)	0.0519 (5)
H12	−0.122409	0.185946	0.184374	0.062*
C13	0.0185 (3)	0.22981 (12)	0.1105 (2)	0.0680 (7)
C14	−0.0232 (3)	0.21119 (17)	−0.0070 (2)	0.1011 (12)
H14	−0.085904	0.181396	−0.021709	0.121*
C15	0.0287 (5)	0.2370 (3)	−0.1013 (3)	0.145 (2)
H15	0.000901	0.223983	−0.179177	0.173*
C16	0.1202 (6)	0.2813 (2)	−0.0823 (5)	0.144 (3)
H16	0.153730	0.298948	−0.146468	0.173*
C17	0.1613 (4)	0.29910 (15)	0.0329 (4)	0.1202 (16)
C18	0.1107 (3)	0.27333 (12)	0.1287 (3)	0.0807 (8)
H18	0.140264	0.285992	0.206414	0.097*
C19	−0.05774 (18)	0.25090 (9)	0.30708 (16)	0.0436 (5)
C20	−0.1629 (2)	0.29297 (10)	0.26751 (18)	0.0472 (5)
C21	−0.2648 (3)	0.38644 (12)	0.3016 (2)	0.0739 (8)
H21A	−0.344665	0.368346	0.317869	0.089*
H21B	−0.273729	0.397671	0.217502	0.089*
C22	−0.2347 (5)	0.43973 (18)	0.3772 (4)	0.155 (2)
H22A	−0.239300	0.429377	0.459385	0.232*
H22B	−0.295244	0.471344	0.352380	0.232*
H22C	−0.149612	0.453524	0.369464	0.232*
C23	0.02010 (18)	0.25477 (8)	0.41280 (17)	0.0406 (4)
C24	0.0185 (2)	0.30256 (9)	0.50681 (18)	0.0441 (5)
C25	−0.0794 (3)	0.30666 (11)	0.5760 (2)	0.0629 (6)
H25	−0.146413	0.278868	0.564751	0.075*
C26	−0.0796 (3)	0.35092 (14)	0.6608 (2)	0.0842 (9)
H26	−0.147338	0.353369	0.705811	0.101*
C27	0.0169 (4)	0.39077 (16)	0.6798 (3)	0.0992 (11)
H27	0.014864	0.421235	0.736649	0.119*
C28	0.1178 (4)	0.38710 (14)	0.6167 (4)	0.1079 (12)
H28	0.186047	0.414051	0.631768	0.129*
C29	0.1177 (3)	0.34263 (12)	0.5293 (3)	0.0770 (8)
H29	0.186363	0.340110	0.485386	0.092*
N1	0.11284 (16)	0.21111 (7)	0.44327 (14)	0.0462 (4)
H1A	0.170700	0.217468	0.503767	0.055*
O1	0.14323 (16)	0.06147 (7)	0.21670 (14)	0.0619 (4)
O2	−0.0565 (2)	0.07963 (10)	0.1336 (2)	0.1071 (8)
O3	−0.24413 (15)	0.28243 (7)	0.18351 (14)	0.0628 (4)
O4	−0.16058 (17)	0.34422 (8)	0.32941 (14)	0.0711 (5)
Cl1	0.28030 (17)	0.35347 (5)	0.05870 (16)	0.1984 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0512 (13)	0.0519 (13)	0.0526 (13)	0.0048 (10)	0.0046 (10)	0.0055 (10)
C2	0.0581 (15)	0.0794 (18)	0.0730 (17)	0.0181 (13)	0.0034 (12)	0.0111 (14)
C3	0.092 (2)	0.0653 (17)	0.0690 (17)	0.0340 (15)	0.0064 (15)	0.0140 (13)
C4	0.102 (2)	0.0452 (14)	0.0692 (17)	0.0037 (14)	0.0108 (15)	0.0105 (12)
C5	0.0644 (14)	0.0484 (13)	0.0596 (14)	−0.0065 (11)	0.0007 (11)	0.0016 (11)
C6	0.0506 (12)	0.0378 (11)	0.0388 (11)	0.0021 (9)	0.0020 (9)	−0.0025 (8)
C7	0.0449 (11)	0.0408 (11)	0.0385 (11)	0.0007 (8)	−0.0001 (8)	−0.0020 (9)
C8	0.0507 (12)	0.0455 (12)	0.0403 (11)	0.0044 (9)	−0.0022 (9)	−0.0040 (9)
C9	0.0644 (15)	0.0546 (14)	0.0524 (13)	0.0029 (12)	−0.0039 (11)	−0.0124 (11)
C10	0.104 (2)	0.0551 (15)	0.092 (2)	0.0035 (15)	0.0138 (17)	−0.0272 (15)
C11	0.159 (4)	0.082 (2)	0.128 (3)	0.041 (2)	0.021 (3)	−0.018 (2)
C12	0.0555 (13)	0.0601 (13)	0.0364 (11)	0.0111 (10)	−0.0068 (9)	−0.0072 (10)
C13	0.0911 (18)	0.0708 (15)	0.0426 (13)	0.0412 (11)	0.0110 (12)	0.0098 (12)
C14	0.118 (3)	0.143 (3)	0.0401 (15)	0.069 (2)	0.0038 (15)	−0.0026 (17)
C15	0.185 (5)	0.209 (6)	0.0444 (18)	0.129 (4)	0.033 (3)	0.029 (3)
C16	0.199 (5)	0.150 (4)	0.106 (4)	0.124 (4)	0.101 (4)	0.076 (3)
C17	0.168 (4)	0.078 (2)	0.138 (3)	0.066 (2)	0.104 (3)	0.053 (2)
C18	0.111 (2)	0.0641 (16)	0.0769 (18)	0.0324 (12)	0.0474 (17)	0.0209 (14)
C19	0.0483 (11)	0.0482 (12)	0.0327 (10)	0.0067 (9)	−0.0002 (8)	−0.0019 (9)
C20	0.0525 (12)	0.0559 (13)	0.0328 (10)	0.0070 (10)	0.0050 (9)	0.0042 (10)
C21	0.0843 (19)	0.0685 (16)	0.0691 (16)	0.0350 (14)	0.0107 (14)	0.0115 (14)
C22	0.221 (5)	0.117 (3)	0.110 (3)	0.104 (3)	−0.036 (3)	−0.041 (2)
C23	0.0440 (11)	0.0396 (10)	0.0373 (10)	0.0006 (8)	0.0022 (8)	−0.0002 (8)
C24	0.0490 (12)	0.0406 (11)	0.0389 (11)	0.0031 (9)	−0.0072 (9)	−0.0024 (9)
C25	0.0761 (17)	0.0670 (15)	0.0465 (13)	−0.0036 (12)	0.0120 (12)	−0.0082 (11)
C26	0.113 (2)	0.094 (2)	0.0462 (15)	0.024 (2)	0.0122 (15)	−0.0156 (15)
C27	0.120 (3)	0.084 (2)	0.083 (2)	0.030 (2)	−0.025 (2)	−0.0421 (18)
C28	0.097 (2)	0.0656 (19)	0.149 (3)	−0.0134 (17)	−0.027 (2)	−0.042 (2)
C29	0.0648 (16)	0.0627 (16)	0.103 (2)	−0.0076 (13)	0.0079 (15)	−0.0216 (15)
N1	0.0510 (10)	0.0421 (9)	0.0407 (9)	0.0060 (8)	−0.0105 (7)	−0.0062 (7)
O1	0.0737 (11)	0.0501 (9)	0.0595 (10)	0.0076 (8)	0.0005 (8)	−0.0173 (7)
O2	0.0845 (14)	0.0985 (15)	0.1233 (17)	0.0145 (12)	−0.0388 (13)	−0.0616 (14)
O3	0.0619 (10)	0.0706 (11)	0.0497 (9)	0.0097 (8)	−0.0143 (8)	0.0042 (8)
O4	0.0870 (12)	0.0666 (11)	0.0532 (10)	0.0368 (9)	−0.0139 (8)	−0.0104 (8)
Cl1	0.2676 (17)	0.0805 (7)	0.2945 (19)	0.0159 (8)	0.2084 (16)	0.0452 (8)

Geometric parameters (Å, º) top

C1—C6	1.379 (3)	C15—C16	1.369 (7)
C1—C2	1.380 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.366 (7)
C2—C3	1.369 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.387 (4)
C3—C4	1.366 (4)	C17—Cl1	1.729 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.378 (3)	C19—C23	1.351 (3)
C4—H4	0.9300	C19—C20	1.465 (3)
C5—C6	1.385 (3)	C20—O3	1.207 (2)
C5—H5	0.9300	C20—O4	1.326 (3)
C6—C7	1.487 (3)	C21—O4	1.440 (3)
C7—C8	1.346 (3)	C21—C22	1.460 (5)
C7—N1	1.385 (2)	C21—H21A	0.9700
C8—C9	1.479 (3)	C21—H21B	0.9700
C8—C12	1.518 (3)	C22—H22A	0.9600
C9—O2	1.199 (3)	C22—H22B	0.9600
C9—O1	1.326 (3)	C22—H22C	0.9600
C10—O1	1.451 (3)	C23—N1	1.380 (2)
C10—C11	1.481 (4)	C23—C24	1.495 (3)
C10—H10A	0.9700	C24—C29	1.365 (3)
C10—H10B	0.9700	C24—C25	1.375 (3)
C11—H11A	0.9600	C25—C26	1.366 (4)
C11—H11B	0.9600	C25—H25	0.9300
C11—H11C	0.9600	C26—C27	1.338 (5)
C12—C13	1.516 (3)	C26—H26	0.9300
C12—C19	1.516 (3)	C27—C28	1.357 (5)
C12—H12	0.9800	C27—H27	0.9300
C13—C18	1.360 (4)	C28—C29	1.389 (4)
C13—C14	1.395 (4)	C28—H28	0.9300
C14—C15	1.380 (6)	C29—H29	0.9300
C14—H14	0.9300	N1—H1A	0.8600

C6—C1—C2	120.4 (2)	C17—C16—C15	118.5 (4)
C6—C1—H1	119.8	C17—C16—H16	120.8
C2—C1—H1	119.8	C15—C16—H16	120.8
C3—C2—C1	120.1 (3)	C16—C17—C18	120.9 (5)
C3—C2—H2	119.9	C16—C17—Cl1	119.1 (3)
C1—C2—H2	119.9	C18—C17—Cl1	120.0 (4)
C4—C3—C2	120.1 (2)	C13—C18—C17	120.9 (4)
C4—C3—H3	120.0	C13—C18—H18	119.5
C2—C3—H3	120.0	C17—C18—H18	119.5
C3—C4—C5	120.2 (2)	C23—C19—C20	124.64 (18)
C3—C4—H4	119.9	C23—C19—C12	121.34 (18)
C5—C4—H4	119.9	C20—C19—C12	113.96 (16)
C4—C5—C6	120.3 (2)	O3—C20—O4	122.37 (19)
C4—C5—H5	119.8	O3—C20—C19	122.7 (2)
C6—C5—H5	119.8	O4—C20—C19	114.95 (18)
C1—C6—C5	118.9 (2)	O4—C21—C22	107.3 (2)
C1—C6—C7	120.52 (18)	O4—C21—H21A	110.3
C5—C6—C7	120.57 (19)	C22—C21—H21A	110.3
C8—C7—N1	120.27 (17)	O4—C21—H21B	110.3
C8—C7—C6	126.50 (18)	C22—C21—H21B	110.3
N1—C7—C6	113.18 (16)	H21A—C21—H21B	108.5
C7—C8—C9	123.88 (19)	C21—C22—H22A	109.5
C7—C8—C12	121.08 (18)	C21—C22—H22B	109.5
C9—C8—C12	115.03 (17)	H22A—C22—H22B	109.5
O2—C9—O1	122.6 (2)	C21—C22—H22C	109.5
O2—C9—C8	123.3 (2)	H22A—C22—H22C	109.5
O1—C9—C8	114.02 (19)	H22B—C22—H22C	109.5
O1—C10—C11	107.6 (2)	C19—C23—N1	119.80 (17)
O1—C10—H10A	110.2	C19—C23—C24	127.08 (17)
C11—C10—H10A	110.2	N1—C23—C24	113.12 (16)
O1—C10—H10B	110.2	C29—C24—C25	117.7 (2)
C11—C10—H10B	110.2	C29—C24—C23	120.3 (2)
H10A—C10—H10B	108.5	C25—C24—C23	121.89 (19)
C10—C11—H11A	109.5	C26—C25—C24	121.0 (3)
C10—C11—H11B	109.5	C26—C25—H25	119.5
H11A—C11—H11B	109.5	C24—C25—H25	119.5
C10—C11—H11C	109.5	C27—C26—C25	120.5 (3)
H11A—C11—H11C	109.5	C27—C26—H26	119.8
H11B—C11—H11C	109.5	C25—C26—H26	119.8
C13—C12—C19	110.89 (19)	C26—C27—C28	120.5 (3)
C13—C12—C8	111.17 (18)	C26—C27—H27	119.7
C19—C12—C8	111.44 (16)	C28—C27—H27	119.7
C13—C12—H12	107.7	C27—C28—C29	119.2 (3)
C19—C12—H12	107.7	C27—C28—H28	120.4
C8—C12—H12	107.7	C29—C28—H28	120.4
C18—C13—C14	118.4 (3)	C24—C29—C28	120.9 (3)
C18—C13—C12	120.7 (2)	C24—C29—H29	119.5
C14—C13—C12	121.0 (3)	C28—C29—H29	119.5
C15—C14—C13	120.0 (4)	C23—N1—C7	122.35 (16)
C15—C14—H14	120.0	C23—N1—H1A	118.8
C13—C14—H14	120.0	C7—N1—H1A	118.8
C16—C15—C14	121.2 (5)	C9—O1—C10	117.38 (19)
C16—C15—H15	119.4	C20—O4—C21	118.62 (19)
C14—C15—H15	119.4

C6—C1—C2—C3	−0.1 (4)	C16—C17—C18—C13	−0.2 (5)
C1—C2—C3—C4	−1.6 (4)	Cl1—C17—C18—C13	−179.0 (2)
C2—C3—C4—C5	1.6 (4)	C13—C12—C19—C23	−106.0 (2)
C3—C4—C5—C6	0.2 (4)	C8—C12—C19—C23	18.4 (3)
C2—C1—C6—C5	1.8 (3)	C13—C12—C19—C20	71.5 (2)
C2—C1—C6—C7	−179.8 (2)	C8—C12—C19—C20	−164.12 (18)
C4—C5—C6—C1	−1.9 (3)	C23—C19—C20—O3	−166.5 (2)
C4—C5—C6—C7	179.7 (2)	C12—C19—C20—O3	16.2 (3)
C1—C6—C7—C8	120.3 (2)	C23—C19—C20—O4	14.9 (3)
C5—C6—C7—C8	−61.3 (3)	C12—C19—C20—O4	−162.47 (18)
C1—C6—C7—N1	−62.4 (2)	C20—C19—C23—N1	177.24 (18)
C5—C6—C7—N1	116.0 (2)	C12—C19—C23—N1	−5.6 (3)
N1—C7—C8—C9	−176.6 (2)	C20—C19—C23—C24	−2.3 (3)
C6—C7—C8—C9	0.5 (3)	C12—C19—C23—C24	174.84 (19)
N1—C7—C8—C12	2.0 (3)	C19—C23—C24—C29	−111.8 (3)
C6—C7—C8—C12	179.1 (2)	N1—C23—C24—C29	68.6 (3)
C7—C8—C9—O2	150.2 (3)	C19—C23—C24—C25	70.4 (3)
C12—C8—C9—O2	−28.4 (4)	N1—C23—C24—C25	−109.2 (2)
C7—C8—C9—O1	−31.4 (3)	C29—C24—C25—C26	2.6 (4)
C12—C8—C9—O1	150.0 (2)	C23—C24—C25—C26	−179.5 (2)
C7—C8—C12—C13	107.7 (2)	C24—C25—C26—C27	−1.1 (4)
C9—C8—C12—C13	−73.6 (3)	C25—C26—C27—C28	−1.3 (5)
C7—C8—C12—C19	−16.6 (3)	C26—C27—C28—C29	2.1 (5)
C9—C8—C12—C19	162.14 (18)	C25—C24—C29—C28	−1.8 (4)
C19—C12—C13—C18	39.7 (3)	C23—C24—C29—C28	−179.7 (3)
C8—C12—C13—C18	−84.9 (3)	C27—C28—C29—C24	−0.4 (5)
C19—C12—C13—C14	−139.9 (2)	C19—C23—N1—C7	−11.5 (3)
C8—C12—C13—C14	95.6 (3)	C24—C23—N1—C7	168.13 (17)
C18—C13—C14—C15	−0.2 (4)	C8—C7—N1—C23	13.4 (3)
C12—C13—C14—C15	179.3 (3)	C6—C7—N1—C23	−164.10 (17)
C13—C14—C15—C16	−0.6 (6)	O2—C9—O1—C10	−9.3 (4)
C14—C15—C16—C17	1.0 (7)	C8—C9—O1—C10	172.2 (2)
C15—C16—C17—C18	−0.6 (6)	C11—C10—O1—C9	179.2 (3)
C15—C16—C17—Cl1	178.1 (3)	O3—C20—O4—C21	5.3 (3)
C14—C13—C18—C17	0.7 (4)	C19—C20—O4—C21	−176.1 (2)
C12—C13—C18—C17	−178.9 (2)	C22—C21—O4—C20	−176.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.10	2.910 (2)	158

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors thank the college management and the Principal for their support and providing the necessary facilities.

References

Ahamed, F. M. M., Padusha, M. S. A. & Gunasekaran, B. (2016). IUCrData, 1, x160155. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, K., Wang, Y., Yao, M. & Xu, D. (2013). Acta Cryst. E69, o785. CSD CrossRef IUCr Journals Google Scholar

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