Ethyl {[5-acetyl-3-cyano-4-(4-meth­oxy­phen­yl)-6-methyl­pyridin-2-yl]sulfan­yl}acetate

Al-Taifi, E.A.; Kaur, M.; Mohamed, S.K.; Akkurt, M.; Jasinski, J.P.

doi:10.1107/S2414314616017156

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161715

https://doi.org/10.1107/S2414314616017156

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Ethyl {[5-acetyl-3-cyano-4-(4-methoxyphenyl)-6-methylpyridin-2-yl]sulfanyl}acetate

Elham A. Al-Taifi,^a ^* Manpreet Kaur,^b Shaaban K. Mohamed,^c,^d Mehmet Akkurt ^e and Jerry P. Jasinski ^b

^aDepartment of Chemistry, Faculty of Science, Sana'a University, Sana'a, Yemen, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, and ^eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by R. J. Butcher, Howard University, USA (Received 28 September 2016; accepted 25 October 2016; online 1 November 2016)

In the title molecule, C₂₀H₂₀N₂O₄S, the dihedral angle between the benzene and pyridine rings is 60.97 (7)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional network.

Keywords: crystal structure; pyridine ring; cyano group; hydrogen bonding; ethyl acetate derivative.

CCDC reference: 1511438

Structure description

Pyridine scaffold compounds continue to attract great interest due to their wide variety of interesting biological activities. They exhibit anticancer, analgesic, antimicrobial and antidepressant activities (Kumar et al., 2011 ). In addition, pyridines are used in the pharmaceutical industry as raw materials for various drugs, vitamins and fungicides (Kumar et al., 2011). These facts promoted us to synthesize and determine the crystal structure of the title compound.

The dihedral angle between the benzene and pyridine rings of the title molecule (Fig. 1) is 60.97 (7)°. The torsion C10—C11—O4—C20, C5—C6—C15—C16, C5—C6—C15—O3, N1—C3—S1—C2, C3—S1—C2—C1, C2—C1—O2—C18 and C1—O2—C18—C19 are 3.6 (2), 73.37 (19), −109.33 (17), −20.05 (13), −73.89 (12), −174.92 (13) and 75.85 (18), respectively. All bonds and bond angles in the title molecule are within the normal range.

Figure 1
The title molecule shown with 50% probability displacement ellipsoids.

In the crystal structure, adjacent molecules are connected via C—H⋯O hydrogen bonds and C—H⋯π interactions with each to other, forming a three-dimensional network (Fig. 2 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the pyridine (N1/C3–C7) and benzene (C8–C13) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.99	2.52	3.150 (2)	121
C2—H2B⋯O1ⁱⁱ	0.99	2.52	3.3345 (19)	140
C19—H19C⋯O2ⁱⁱⁱ	0.98	2.65	3.437 (2)	138
C9—H9⋯Cg2^iv	0.95	2.88	3.7803 (17)	159
C20—H20B⋯Cg1^v	0.98	2.84	3.5619 (18)	131
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+2, -z+2; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Packing of the title molecule viewed down the c axis with the hydrogen bonds shown by dotted lines.

Synthesis and crystallization

To a mixture of 5-acetyl-3-cyano-4-(4-methoxyphenyl)-6-methylpyridine-2(1H)-thione (10 mmol) and ethyl chloroacetate (10 mmol) in ethanol (20 ml), sodium acetate trihydrate (11 mmol) was added. The resulting mixture was heated under reflux for 2 h and then allowed to cool. The precipitated solid was collected and recrystallized from ethanol (yield 98%; m.p. 409–410 K). IR: 2200 (CN), 1730 (C=O, ester), 1690 (C=O, acetyl) cm^{-1. 1}H NMR (CDCl₃): 6.9–7.4 (dd, 4H, ArH); 4.1–4.3 (q, 2H, OCH₂); 3.9 (s, 2H, SCH₂); 3.7 (s, 3H, OCH₃); 2.4 (s, 3H, COCH₃); 1.8 (s, 3H, CH₃ at C-6); 1.1–1.3 (t, 3H, CH₃ of ester).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂O₄S
M_r	384.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.4883 (2), 8.23273 (16), 16.8923 (3)
β (°)	93.8000 (17)
V (Å³)	1871.69 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.78
Crystal size (mm)	0.49 × 0.46 × 0.22

Data collection
Diffractometer	Rigaku Oxford Diffraction
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.600, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6913, 3553, 3278
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.05
No. of reflections	3553
No. of parameters	249
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1511438

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017156/bv4005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017156/bv4005Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616017156/bv4005Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Ethyl {[5-acetyl-3-cyano-4-(4-methoxyphenyl)-6-methylpyridin-2-yl]sulfanyl}acetate top

Crystal data top

C₂₀H₂₀N₂O₄S	F(000) = 808
M_r = 384.44	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.4883 (2) Å	Cell parameters from 3634 reflections
b = 8.23273 (16) Å	θ = 4.1–71.5°
c = 16.8923 (3) Å	µ = 1.78 mm⁻¹
β = 93.8000 (17)°	T = 173 K
V = 1871.69 (6) Å³	Irregular, colourless
Z = 4	0.49 × 0.46 × 0.22 mm

Data collection top

Rigaku Oxford Diffraction diffractometer	3553 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3278 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.2°, θ_min = 3.3°
ω scans	h = −16→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −9→6
T_min = 0.600, T_max = 1.000	l = −20→20
6913 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0702P)² + 0.4141P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.29 e Å⁻³
3553 reflections	Δρ_min = −0.29 e Å⁻³
249 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0045 (4)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq
S1	0.62202 (3)	1.02799 (5)	0.73252 (2)	0.02850 (15)
O1	0.41273 (8)	0.94698 (14)	0.79041 (6)	0.0281 (3)
O2	0.45128 (8)	1.05466 (14)	0.91107 (6)	0.0282 (3)
O3	0.75861 (9)	0.29044 (14)	0.87453 (8)	0.0367 (3)
O4	1.05277 (9)	0.32068 (14)	0.56752 (7)	0.0331 (3)
N1	0.63715 (9)	0.78612 (15)	0.83887 (7)	0.0222 (3)
N2	0.80930 (12)	0.90691 (19)	0.60820 (9)	0.0378 (4)
C1	0.46752 (11)	1.02342 (17)	0.83507 (9)	0.0222 (3)
C2	0.56182 (11)	1.10919 (18)	0.81526 (9)	0.0248 (3)
H2A	0.6093	1.1056	0.8625	0.030*
H2B	0.5460	1.2247	0.8043	0.030*
C3	0.67375 (10)	0.84809 (18)	0.77408 (8)	0.0212 (3)
C4	0.75159 (10)	0.77387 (18)	0.73602 (8)	0.0208 (3)
C5	0.79313 (10)	0.62958 (18)	0.76679 (8)	0.0204 (3)
C6	0.75585 (10)	0.56783 (18)	0.83602 (8)	0.0207 (3)
C7	0.67650 (10)	0.64734 (18)	0.86890 (8)	0.0217 (3)
C8	0.86906 (11)	0.54322 (18)	0.72251 (8)	0.0208 (3)
C9	0.95693 (11)	0.61926 (19)	0.70468 (9)	0.0254 (3)
H9	0.9722	0.7235	0.7262	0.030*
C10	1.02267 (11)	0.54571 (19)	0.65599 (9)	0.0243 (3)
H10	1.0839	0.5966	0.6463	0.029*
C11	0.99780 (11)	0.39687 (18)	0.62161 (9)	0.0231 (3)
C12	0.91130 (11)	0.31666 (18)	0.64035 (9)	0.0245 (3)
H12	0.8958	0.2131	0.6180	0.029*
C13	0.84814 (10)	0.38804 (18)	0.69154 (9)	0.0221 (3)
H13	0.7905	0.3317	0.7057	0.027*
C14	0.78475 (11)	0.84630 (19)	0.66472 (9)	0.0254 (3)
C15	0.80209 (11)	0.41777 (18)	0.87574 (8)	0.0221 (3)
C16	0.90163 (13)	0.4406 (2)	0.91893 (11)	0.0347 (4)
H16A	0.8959	0.5187	0.9622	0.052*
H16B	0.9488	0.4817	0.8821	0.052*
H16C	0.9253	0.3363	0.9408	0.052*
C17	0.62897 (13)	0.5812 (2)	0.94013 (10)	0.0302 (4)
H17A	0.5897	0.6668	0.9635	0.045*
H17B	0.6807	0.5437	0.9794	0.045*
H17C	0.5855	0.4901	0.9240	0.045*
C18	0.35925 (12)	0.9943 (2)	0.94011 (10)	0.0300 (4)
H18A	0.3038	1.0188	0.9006	0.036*
H18B	0.3462	1.0517	0.9899	0.036*
C19	0.36222 (13)	0.8147 (2)	0.95549 (10)	0.0340 (4)
H19A	0.3677	0.7566	0.9053	0.051*
H19B	0.3012	0.7813	0.9794	0.051*
H19C	0.4197	0.7888	0.9918	0.051*
C20	1.13748 (12)	0.4044 (2)	0.54211 (10)	0.0327 (4)
H20A	1.1696	0.3381	0.5030	0.049*
H20B	1.1845	0.4244	0.5878	0.049*
H20C	1.1166	0.5083	0.5180	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0316 (2)	0.0278 (2)	0.0272 (2)	0.00865 (15)	0.01043 (16)	0.00996 (14)
O1	0.0252 (5)	0.0322 (6)	0.0262 (6)	−0.0021 (5)	−0.0026 (4)	−0.0026 (4)
O2	0.0259 (5)	0.0345 (6)	0.0248 (6)	−0.0081 (5)	0.0054 (4)	−0.0048 (4)
O3	0.0307 (6)	0.0269 (6)	0.0525 (7)	−0.0050 (5)	0.0021 (5)	0.0100 (5)
O4	0.0322 (6)	0.0278 (6)	0.0413 (6)	0.0027 (5)	0.0161 (5)	−0.0049 (5)
N1	0.0195 (6)	0.0241 (6)	0.0234 (6)	0.0019 (5)	0.0037 (5)	0.0025 (5)
N2	0.0459 (9)	0.0391 (8)	0.0298 (7)	0.0026 (7)	0.0132 (6)	0.0077 (6)
C1	0.0222 (7)	0.0207 (7)	0.0235 (7)	0.0042 (6)	0.0010 (6)	0.0022 (6)
C2	0.0251 (7)	0.0211 (7)	0.0288 (7)	0.0009 (6)	0.0075 (6)	0.0008 (6)
C3	0.0189 (7)	0.0226 (7)	0.0221 (7)	−0.0005 (5)	0.0012 (5)	0.0018 (5)
C4	0.0202 (6)	0.0230 (7)	0.0195 (6)	−0.0021 (5)	0.0029 (5)	0.0005 (5)
C5	0.0172 (6)	0.0230 (7)	0.0208 (6)	−0.0024 (5)	0.0008 (5)	−0.0020 (6)
C6	0.0186 (7)	0.0214 (7)	0.0219 (7)	−0.0016 (5)	0.0000 (5)	0.0001 (6)
C7	0.0206 (7)	0.0237 (7)	0.0207 (7)	−0.0020 (6)	0.0016 (5)	0.0011 (6)
C8	0.0186 (7)	0.0236 (7)	0.0201 (7)	0.0016 (5)	0.0004 (5)	0.0010 (5)
C9	0.0233 (7)	0.0258 (8)	0.0270 (7)	−0.0044 (6)	0.0018 (6)	−0.0041 (6)
C10	0.0189 (7)	0.0262 (8)	0.0279 (7)	−0.0019 (6)	0.0030 (6)	0.0001 (6)
C11	0.0228 (7)	0.0228 (7)	0.0240 (7)	0.0053 (6)	0.0035 (6)	0.0026 (6)
C12	0.0250 (7)	0.0200 (7)	0.0285 (7)	0.0001 (6)	0.0019 (6)	0.0000 (6)
C13	0.0188 (7)	0.0225 (7)	0.0250 (7)	−0.0003 (5)	0.0014 (5)	0.0029 (6)
C14	0.0252 (7)	0.0260 (8)	0.0254 (8)	0.0011 (6)	0.0051 (6)	0.0003 (6)
C15	0.0236 (7)	0.0219 (7)	0.0214 (7)	0.0020 (6)	0.0058 (5)	0.0010 (6)
C16	0.0357 (9)	0.0247 (8)	0.0416 (10)	0.0044 (7)	−0.0126 (7)	−0.0005 (7)
C17	0.0317 (8)	0.0309 (8)	0.0291 (8)	0.0052 (7)	0.0115 (6)	0.0082 (7)
C18	0.0246 (8)	0.0367 (9)	0.0294 (8)	−0.0035 (7)	0.0077 (6)	−0.0032 (7)
C19	0.0348 (8)	0.0386 (9)	0.0292 (8)	−0.0068 (7)	0.0055 (7)	0.0022 (7)
C20	0.0278 (8)	0.0364 (9)	0.0352 (8)	0.0043 (7)	0.0127 (7)	0.0006 (7)

Geometric parameters (Å, º) top

S1—C2	1.7917 (15)	C9—H9	0.9500
S1—C3	1.7630 (15)	C9—C10	1.388 (2)
O1—C1	1.1988 (19)	C10—H10	0.9500
O2—C1	1.3415 (18)	C10—C11	1.388 (2)
O2—C18	1.4522 (19)	C11—C12	1.395 (2)
O3—C15	1.201 (2)	C12—H12	0.9500
O4—C11	1.3666 (18)	C12—C13	1.384 (2)
O4—C20	1.425 (2)	C13—H13	0.9500
N1—C3	1.3318 (18)	C15—C16	1.497 (2)
N1—C7	1.345 (2)	C16—H16A	0.9800
N2—C14	1.145 (2)	C16—H16B	0.9800
C1—C2	1.512 (2)	C16—H16C	0.9800
C2—H2A	0.9900	C17—H17A	0.9800
C2—H2B	0.9900	C17—H17B	0.9800
C3—C4	1.407 (2)	C17—H17C	0.9800
C4—C5	1.399 (2)	C18—H18A	0.9900
C4—C14	1.441 (2)	C18—H18B	0.9900
C5—C6	1.399 (2)	C18—C19	1.502 (2)
C5—C8	1.489 (2)	C19—H19A	0.9800
C6—C7	1.400 (2)	C19—H19B	0.9800
C6—C15	1.520 (2)	C19—H19C	0.9800
C7—C17	1.502 (2)	C20—H20A	0.9800
C8—C9	1.391 (2)	C20—H20B	0.9800
C8—C13	1.402 (2)	C20—H20C	0.9800

C3—S1—C2	100.99 (7)	C11—C12—H12	120.0
C1—O2—C18	117.07 (12)	C13—C12—C11	119.96 (14)
C11—O4—C20	117.44 (13)	C13—C12—H12	120.0
C3—N1—C7	118.48 (12)	C8—C13—H13	119.9
O1—C1—O2	124.74 (14)	C12—C13—C8	120.19 (13)
O1—C1—C2	126.77 (14)	C12—C13—H13	119.9
O2—C1—C2	108.39 (12)	N2—C14—C4	178.24 (17)
S1—C2—H2A	108.4	O3—C15—C6	121.09 (13)
S1—C2—H2B	108.4	O3—C15—C16	122.63 (14)
C1—C2—S1	115.46 (11)	C16—C15—C6	116.22 (13)
C1—C2—H2A	108.4	C15—C16—H16A	109.5
C1—C2—H2B	108.4	C15—C16—H16B	109.5
H2A—C2—H2B	107.5	C15—C16—H16C	109.5
N1—C3—S1	119.38 (11)	H16A—C16—H16B	109.5
N1—C3—C4	122.54 (13)	H16A—C16—H16C	109.5
C4—C3—S1	118.07 (11)	H16B—C16—H16C	109.5
C3—C4—C14	118.99 (13)	C7—C17—H17A	109.5
C5—C4—C3	119.46 (13)	C7—C17—H17B	109.5
C5—C4—C14	121.53 (13)	C7—C17—H17C	109.5
C4—C5—C6	117.52 (13)	H17A—C17—H17B	109.5
C4—C5—C8	119.40 (12)	H17A—C17—H17C	109.5
C6—C5—C8	122.95 (13)	H17B—C17—H17C	109.5
C5—C6—C7	119.22 (13)	O2—C18—H18A	109.1
C5—C6—C15	120.31 (13)	O2—C18—H18B	109.1
C7—C6—C15	120.46 (13)	O2—C18—C19	112.44 (14)
N1—C7—C6	122.72 (13)	H18A—C18—H18B	107.8
N1—C7—C17	115.53 (13)	C19—C18—H18A	109.1
C6—C7—C17	121.75 (13)	C19—C18—H18B	109.1
C9—C8—C5	121.23 (13)	C18—C19—H19A	109.5
C9—C8—C13	118.85 (13)	C18—C19—H19B	109.5
C13—C8—C5	119.64 (13)	C18—C19—H19C	109.5
C8—C9—H9	119.4	H19A—C19—H19B	109.5
C10—C9—C8	121.27 (14)	H19A—C19—H19C	109.5
C10—C9—H9	119.4	H19B—C19—H19C	109.5
C9—C10—H10	120.4	O4—C20—H20A	109.5
C11—C10—C9	119.14 (14)	O4—C20—H20B	109.5
C11—C10—H10	120.4	O4—C20—H20C	109.5
O4—C11—C10	123.93 (13)	H20A—C20—H20B	109.5
O4—C11—C12	115.68 (14)	H20A—C20—H20C	109.5
C10—C11—C12	120.37 (14)	H20B—C20—H20C	109.5

S1—C3—C4—C5	−178.97 (11)	C5—C8—C13—C12	170.24 (13)
S1—C3—C4—C14	−0.71 (19)	C6—C5—C8—C9	−125.95 (16)
O1—C1—C2—S1	−25.7 (2)	C6—C5—C8—C13	60.16 (19)
O2—C1—C2—S1	157.87 (10)	C7—N1—C3—S1	178.89 (10)
O4—C11—C12—C13	−176.80 (13)	C7—N1—C3—C4	0.1 (2)
N1—C3—C4—C5	−0.2 (2)	C7—C6—C15—O3	71.7 (2)
N1—C3—C4—C14	178.08 (13)	C7—C6—C15—C16	−105.64 (17)
C1—O2—C18—C19	75.85 (18)	C8—C5—C6—C7	−172.72 (13)
C2—S1—C3—N1	20.05 (13)	C8—C5—C6—C15	8.3 (2)
C2—S1—C3—C4	−161.11 (12)	C8—C9—C10—C11	3.0 (2)
C3—S1—C2—C1	−73.89 (12)	C9—C8—C13—C12	−3.8 (2)
C3—N1—C7—C6	1.6 (2)	C9—C10—C11—O4	174.13 (14)
C3—N1—C7—C17	−177.76 (13)	C9—C10—C11—C12	−4.7 (2)
C3—C4—C5—C6	−1.4 (2)	C10—C11—C12—C13	2.1 (2)
C3—C4—C5—C8	174.50 (13)	C11—C12—C13—C8	2.2 (2)
C4—C5—C6—C7	3.1 (2)	C13—C8—C9—C10	1.2 (2)
C4—C5—C6—C15	−175.95 (12)	C14—C4—C5—C6	−179.65 (13)
C4—C5—C8—C9	58.34 (19)	C14—C4—C5—C8	−3.7 (2)
C4—C5—C8—C13	−115.55 (16)	C15—C6—C7—N1	175.72 (13)
C5—C6—C7—N1	−3.3 (2)	C15—C6—C7—C17	−4.9 (2)
C5—C6—C7—C17	176.07 (14)	C18—O2—C1—O1	−1.6 (2)
C5—C6—C15—O3	−109.33 (17)	C18—O2—C1—C2	174.92 (13)
C5—C6—C15—C16	73.37 (19)	C20—O4—C11—C10	−3.6 (2)
C5—C8—C9—C10	−172.76 (14)	C20—O4—C11—C12	175.24 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the pyridine (N1/C3–C7) and benzene (C8–C13) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.99	2.52	3.150 (2)	121
C2—H2B···O1ⁱⁱ	0.99	2.52	3.3345 (19)	140
C19—H19C···O2ⁱⁱⁱ	0.98	2.65	3.437 (2)	138
C9—H9···Cg2^iv	0.95	2.88	3.7803 (17)	159
C20—H20B···Cg1^v	0.98	2.84	3.5619 (18)	131

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+1, −y+2, −z+2; (iv) −x+2, y+1/2, −z+3/2; (v) −x+2, y−1/2, −z+3/2.

Acknowledgements

JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X ray diffractometer.

References

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