Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′-sub­sti­tuted 4-methylchal­cones: 3′-(N=CHC₆H₄-p-CH₃)-4-methyl­chal­cone and 3′-(NHCOCH₃)-4-methylchal­cone

Two crystal structures of chal­cones, or 1,3-di­aryl­prop-2-en-1-ones, are pre­sented; both contain a p-methyl substitution on the 3-Ring, but differ with respect to the m-substitution on the 1-Ring. Their systematic names are (2E)-3-(4-methyl­phen­yl)-1-(3-{[(4-methyl­phen­yl)methyl­idene]amino}­phen­yl)prop-2-en-1-one (C₂₄H₂₁NO) and N-{3-[(2E)-3-(4-methyl­phen­yl)prop-2-eno­yl]phen­yl}acetamide (C₁₈H₁₇NO₂), which are abbreviated as 3′-(N=CHC₆H₄-p-CH₃)-4-methyl­chal­cone and 3′-(NHCOCH₃)-4-methyl­chal­cone, respectively. Both chal­cones represent the first reported acetamide-substituted and imino-substituted chal­cone crystal structures, adding to the robust library of chal­cone structures within the Cambridge Structural Database. The crystal structure of 3′-(N=CHC₆H₄-p-CH₃)-4-methyl­chal­cone exhibits close contacts between the enone O atom and the substituent arene ring, in addition to C...C inter­actions between the substituent arene rings. The structure of 3′-(NHCOCH₃)-4-methyl­chal­cone exhibits a unique inter­action between the enone O atom and the 1-Ring substituent, contributing to its anti­parallel crystal packing. In addition, both structures exhibit π-stacking, which occurs between the 1-Ring and R-Ring for 3′-(N=CHC₆H₄-p-CH₃)-4-methyl­chal­cone, and between the 1-Ring and 3-Ring for 3′-(NHCOCH₃)-4-methyl­chal­cone.

Computing details

For both structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2001), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: X-SEED (Barbour, 2001).

(2E)-3-(4-Methylphenyl)-1-(3-{[(4-methylphenyl)methylidene]amino}phenyl)prop-2-en-1-one (mPMIpCH3)

Crystal data

C24H21NO	F(000) = 1440
Mr = 339.42	Dx = 1.253 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 19.5522 (13) Å	Cell parameters from 4400 reflections
b = 5.8693 (4) Å	θ = 2.8–68.3°
c = 31.3714 (19) Å	µ = 0.59 mm^−1
β = 91.438 (4)°	T = 100 K
V = 3599.0 (4) Å^3	Plate, colourless
Z = 8	0.11 × 0.11 × 0.03 mm

Data collection

Bruker D8 Venture diffractometer	3283 independent reflections
Radiation source: Microsource IuS Incoatec 3.0	2526 reflections with I > 2σ(I)
Double Bounce Multilayer Mirrors monochromator	Rint = 0.043
Detector resolution: 7.9 pixels mm^-1	θmax = 68.3°, θmin = 4.5°
φ and ω scans	h = −22→23
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −6→7
Tmin = 0.684, Tmax = 0.753	l = −37→37
10519 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 2.4974P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3283 reflections	Δρmax = 0.17 e Å^−3
237 parameters	Δρmin = −0.17 e Å^−3
0 restraints

Special details

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. All C-H hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups).

The X-ray intensity data for each chalcone derivative was measured at 100 K on a Bruker Photon II D8 Venture diffractometer equipped with both IµS-Cu and IµS-Mo microfocus X-ray sources. The Cu K_α (λ = 1.54178 Å) source was used for all crystallographic investigations. Data sets were corrected for Lorentz and polarization effects as well as absorption. The criterion for observed reflections was I > 2σ(I). Lattice parameters were determined from least-squares analysis and reflection data. Empirical absorption corrections were applied using SADABS. Structures were solved by direct methods and refined by full-matrix least-squares analysis on F² using X-SEED equipped with SHELXT (Barbour, 2001; Sheldrick, 2015a). All non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F² using the SHELXL program (Sheldrick, 2015b).

Unit-cell projections were visualized with Mercury 2020.1 (Macrae et al., 2020), Hirshfeld analyses were executed with CrystalExplorer17.5 (Turner et al., 2017), while distance/angle measurements, as well as ORTEP images, were captured using OLEX2 (Dolomanov et al., 2009). Electrostatic potential calculations employed GAUSSIAN09 (Frisch et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.49474 (6)	0.52779 (19)	0.65074 (3)	0.0298 (3)
N1	0.35087 (7)	0.5081 (2)	0.51350 (4)	0.0267 (3)
C1	0.48027 (8)	0.3248 (3)	0.64654 (5)	0.0237 (3)
C2	0.51253 (8)	0.1489 (3)	0.67399 (5)	0.0252 (4)
H2	0.493799	−0.000423	0.674354	0.030*
C3	0.56766 (8)	0.1966 (3)	0.69831 (5)	0.0238 (3)
H3	0.585393	0.346729	0.696026	0.029*
C4	0.42985 (8)	0.2539 (3)	0.61228 (5)	0.0219 (3)
C5	0.41504 (8)	0.4089 (3)	0.57967 (5)	0.0232 (3)
H5	0.436777	0.553701	0.579918	0.028*
C6	0.36870 (8)	0.3544 (3)	0.54667 (5)	0.0243 (4)
C7	0.33446 (9)	0.1452 (3)	0.54769 (5)	0.0282 (4)
H7	0.301087	0.108959	0.526220	0.034*
C8	0.34926 (9)	−0.0086 (3)	0.57997 (5)	0.0284 (4)
H8	0.326314	−0.151290	0.580274	0.034*
C9	0.39731 (8)	0.0425 (3)	0.61208 (5)	0.0247 (3)
H9	0.407876	−0.066126	0.633713	0.030*
C10	0.60389 (8)	0.0446 (3)	0.72806 (5)	0.0223 (3)
C11	0.66169 (8)	0.1229 (3)	0.75075 (5)	0.0253 (4)
H11	0.678902	0.270849	0.745028	0.030*
C12	0.69437 (8)	−0.0108 (3)	0.78141 (5)	0.0256 (4)
H12	0.733766	0.046423	0.796165	0.031*
C13	0.67045 (8)	−0.2271 (3)	0.79092 (5)	0.0246 (4)
C14	0.61319 (8)	−0.3070 (3)	0.76779 (5)	0.0252 (4)
H14	0.595879	−0.454531	0.773765	0.030*
C15	0.58130 (8)	−0.1770 (3)	0.73656 (5)	0.0242 (3)
H15	0.543627	−0.238174	0.720646	0.029*
C16	0.39784 (8)	0.6276 (3)	0.49703 (5)	0.0276 (4)
H16	0.443977	0.601924	0.505962	0.033*
C17	0.38331 (8)	0.8029 (3)	0.46486 (5)	0.0260 (4)
C18	0.31642 (8)	0.8442 (3)	0.44997 (5)	0.0262 (4)
H18	0.279837	0.753635	0.459890	0.031*
C19	0.30344 (8)	1.0161 (3)	0.42093 (5)	0.0262 (4)
H19	0.257753	1.042095	0.411094	0.031*
C20	0.35566 (8)	1.1524 (3)	0.40567 (5)	0.0264 (4)
C21	0.42239 (9)	1.1103 (3)	0.42046 (5)	0.0313 (4)
H21	0.458911	1.200764	0.410430	0.038*
C22	0.43590 (8)	0.9378 (3)	0.44961 (5)	0.0306 (4)
H22	0.481619	0.911197	0.459317	0.037*
C23	0.34029 (9)	1.3399 (3)	0.37409 (5)	0.0339 (4)
H23A	0.350244	1.286856	0.345283	0.051*
H23B	0.368749	1.472967	0.381026	0.051*
H23C	0.291888	1.382030	0.375406	0.051*
C24	0.70477 (9)	−0.3717 (3)	0.82490 (5)	0.0308 (4)
H24A	0.731695	−0.491419	0.811428	0.046*
H24B	0.669920	−0.441575	0.842616	0.046*
H24C	0.735007	−0.276230	0.842739	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0368 (7)	0.0227 (6)	0.0295 (6)	−0.0030 (5)	−0.0101 (5)	0.0012 (5)
N1	0.0328 (8)	0.0266 (7)	0.0203 (6)	0.0056 (6)	−0.0060 (6)	−0.0014 (6)
C1	0.0249 (8)	0.0244 (8)	0.0216 (8)	−0.0004 (7)	−0.0011 (6)	0.0018 (6)
C2	0.0281 (8)	0.0229 (8)	0.0244 (8)	−0.0019 (7)	−0.0053 (6)	0.0017 (6)
C3	0.0272 (8)	0.0226 (8)	0.0216 (7)	−0.0020 (7)	−0.0002 (6)	0.0004 (6)
C4	0.0218 (8)	0.0225 (8)	0.0211 (7)	0.0036 (6)	−0.0020 (6)	−0.0017 (6)
C5	0.0252 (8)	0.0217 (8)	0.0226 (7)	0.0035 (7)	−0.0029 (6)	−0.0011 (6)
C6	0.0264 (8)	0.0244 (8)	0.0220 (8)	0.0082 (7)	−0.0030 (6)	−0.0021 (6)
C7	0.0311 (9)	0.0266 (9)	0.0264 (8)	0.0046 (7)	−0.0090 (7)	−0.0057 (7)
C8	0.0296 (9)	0.0228 (8)	0.0324 (9)	0.0001 (7)	−0.0068 (7)	−0.0029 (7)
C9	0.0267 (8)	0.0225 (8)	0.0246 (8)	0.0033 (7)	−0.0034 (6)	−0.0001 (6)
C10	0.0229 (8)	0.0246 (8)	0.0194 (7)	0.0015 (7)	−0.0002 (6)	−0.0004 (6)
C11	0.0270 (8)	0.0213 (8)	0.0275 (8)	−0.0015 (7)	−0.0024 (6)	0.0003 (6)
C12	0.0239 (8)	0.0273 (9)	0.0252 (8)	0.0010 (7)	−0.0069 (6)	−0.0037 (7)
C13	0.0274 (8)	0.0278 (9)	0.0187 (7)	0.0053 (7)	−0.0015 (6)	−0.0006 (6)
C14	0.0277 (8)	0.0219 (8)	0.0260 (8)	−0.0010 (7)	−0.0001 (7)	0.0005 (7)
C15	0.0236 (8)	0.0255 (8)	0.0232 (8)	−0.0003 (7)	−0.0040 (6)	−0.0020 (7)
C16	0.0254 (8)	0.0372 (10)	0.0200 (8)	0.0103 (8)	−0.0036 (6)	−0.0018 (7)
C17	0.0273 (8)	0.0331 (9)	0.0175 (7)	0.0071 (7)	−0.0009 (6)	−0.0021 (7)
C18	0.0248 (8)	0.0319 (9)	0.0219 (8)	0.0005 (7)	−0.0030 (6)	−0.0021 (7)
C19	0.0247 (8)	0.0326 (9)	0.0209 (7)	0.0046 (7)	−0.0057 (6)	−0.0033 (7)
C20	0.0298 (9)	0.0309 (9)	0.0186 (7)	0.0051 (7)	−0.0016 (6)	−0.0022 (7)
C21	0.0265 (9)	0.0423 (10)	0.0250 (8)	0.0001 (8)	0.0001 (7)	0.0041 (7)
C22	0.0232 (8)	0.0454 (11)	0.0230 (8)	0.0062 (8)	−0.0006 (6)	0.0018 (7)
C23	0.0367 (10)	0.0362 (10)	0.0285 (9)	0.0032 (8)	−0.0035 (7)	0.0040 (8)
C24	0.0358 (10)	0.0303 (9)	0.0258 (8)	0.0047 (8)	−0.0064 (7)	0.0032 (7)

Geometric parameters (Å, º)

O1—C1	1.231 (2)	C13—C14	1.400 (2)
N1—C16	1.275 (2)	C13—C24	1.507 (2)
N1—C6	1.414 (2)	C14—C15	1.379 (2)
C1—C2	1.476 (2)	C14—H14	0.9500
C1—C4	1.499 (2)	C15—H15	0.9500
C2—C3	1.335 (2)	C16—C17	1.464 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C10	1.461 (2)	C17—C22	1.392 (2)
C3—H3	0.9500	C17—C18	1.399 (2)
C4—C5	1.394 (2)	C18—C19	1.379 (2)
C4—C9	1.395 (2)	C18—H18	0.9500
C5—C6	1.396 (2)	C19—C20	1.391 (2)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.399 (2)	C20—C21	1.396 (2)
C7—C8	1.382 (2)	C20—C23	1.506 (2)
C7—H7	0.9500	C21—C22	1.385 (2)
C8—C9	1.393 (2)	C21—H21	0.9500
C8—H8	0.9500	C22—H22	0.9500
C9—H9	0.9500	C23—H23A	0.9800
C10—C11	1.398 (2)	C23—H23B	0.9800
C10—C15	1.401 (2)	C23—H23C	0.9800
C11—C12	1.385 (2)	C24—H24A	0.9800
C11—H11	0.9500	C24—H24B	0.9800
C12—C13	1.388 (2)	C24—H24C	0.9800
C12—H12	0.9500
C16—N1—C6	118.85 (14)	C15—C14—C13	121.63 (15)
O1—C1—C2	121.39 (14)	C15—C14—H14	119.2
O1—C1—C4	119.38 (14)	C13—C14—H14	119.2
C2—C1—C4	119.22 (14)	C14—C15—C10	120.66 (15)
C3—C2—C1	120.93 (15)	C14—C15—H15	119.7
C3—C2—H2	119.5	C10—C15—H15	119.7
C1—C2—H2	119.5	N1—C16—C17	122.46 (15)
C2—C3—C10	127.47 (16)	N1—C16—H16	118.8
C2—C3—H3	116.3	C17—C16—H16	118.8
C10—C3—H3	116.3	C22—C17—C18	118.61 (15)
C5—C4—C9	119.42 (14)	C22—C17—C16	120.30 (15)
C5—C4—C1	117.76 (14)	C18—C17—C16	121.05 (16)
C9—C4—C1	122.82 (14)	C19—C18—C17	120.19 (16)
C4—C5—C6	120.91 (15)	C19—C18—H18	119.9
C4—C5—H5	119.5	C17—C18—H18	119.9
C6—C5—H5	119.5	C18—C19—C20	121.58 (15)
C5—C6—C7	119.10 (15)	C18—C19—H19	119.2
C5—C6—N1	122.87 (15)	C20—C19—H19	119.2
C7—C6—N1	117.87 (14)	C19—C20—C21	118.12 (15)
C8—C7—C6	119.91 (15)	C19—C20—C23	120.70 (15)
C8—C7—H7	120.0	C21—C20—C23	121.17 (16)
C6—C7—H7	120.0	C22—C21—C20	120.68 (16)
C7—C8—C9	120.95 (16)	C22—C21—H21	119.7
C7—C8—H8	119.5	C20—C21—H21	119.7
C9—C8—H8	119.5	C21—C22—C17	120.82 (16)
C8—C9—C4	119.63 (15)	C21—C22—H22	119.6
C8—C9—H9	120.2	C17—C22—H22	119.6
C4—C9—H9	120.2	C20—C23—H23A	109.5
C11—C10—C15	117.57 (14)	C20—C23—H23B	109.5
C11—C10—C3	119.80 (15)	H23A—C23—H23B	109.5
C15—C10—C3	122.56 (14)	C20—C23—H23C	109.5
C12—C11—C10	121.34 (15)	H23A—C23—H23C	109.5
C12—C11—H11	119.3	H23B—C23—H23C	109.5
C10—C11—H11	119.3	C13—C24—H24A	109.5
C11—C12—C13	121.03 (15)	C13—C24—H24B	109.5
C11—C12—H12	119.5	H24A—C24—H24B	109.5
C13—C12—H12	119.5	C13—C24—H24C	109.5
C12—C13—C14	117.69 (14)	H24A—C24—H24C	109.5
C12—C13—C24	121.39 (15)	H24B—C24—H24C	109.5
C14—C13—C24	120.93 (15)
O1—C1—C2—C3	−13.4 (2)	C3—C10—C11—C12	175.32 (14)
C4—C1—C2—C3	165.41 (14)	C10—C11—C12—C13	−0.5 (2)
C1—C2—C3—C10	177.79 (14)	C11—C12—C13—C14	1.4 (2)
O1—C1—C4—C5	16.6 (2)	C11—C12—C13—C24	−178.65 (15)
C2—C1—C4—C5	−162.19 (14)	C12—C13—C14—C15	0.1 (2)
O1—C1—C4—C9	−162.82 (15)	C24—C13—C14—C15	−179.88 (15)
C2—C1—C4—C9	18.4 (2)	C13—C14—C15—C10	−2.4 (2)
C9—C4—C5—C6	−0.7 (2)	C11—C10—C15—C14	3.3 (2)
C1—C4—C5—C6	179.86 (14)	C3—C10—C15—C14	−173.79 (14)
C4—C5—C6—C7	3.1 (2)	C6—N1—C16—C17	−175.29 (14)
C4—C5—C6—N1	178.44 (14)	N1—C16—C17—C22	176.32 (16)
C16—N1—C6—C5	41.8 (2)	N1—C16—C17—C18	−1.3 (2)
C16—N1—C6—C7	−142.73 (16)	C22—C17—C18—C19	−0.3 (2)
C5—C6—C7—C8	−3.2 (2)	C16—C17—C18—C19	177.41 (15)
N1—C6—C7—C8	−178.77 (15)	C17—C18—C19—C20	0.0 (2)
C6—C7—C8—C9	0.9 (2)	C18—C19—C20—C21	0.3 (2)
C7—C8—C9—C4	1.5 (2)	C18—C19—C20—C23	−179.74 (15)
C5—C4—C9—C8	−1.7 (2)	C19—C20—C21—C22	−0.2 (2)
C1—C4—C9—C8	177.80 (14)	C23—C20—C21—C22	179.80 (16)
C2—C3—C10—C11	179.24 (16)	C20—C21—C22—C17	−0.1 (3)
C2—C3—C10—C15	−3.8 (3)	C18—C17—C22—C21	0.3 (2)
C15—C10—C11—C12	−1.8 (2)	C16—C17—C22—C21	−177.37 (15)

N-{3-[(2E)-3-(4-Methylphenyl)prop-2-enoyl]phenyl}acetamide (mAApCH3)

Crystal data

C18H17NO2	F(000) = 1184
Mr = 279.32	Dx = 1.306 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 25.1922 (5) Å	Cell parameters from 9920 reflections
b = 5.7621 (1) Å	θ = 3.7–72.1°
c = 20.7012 (4) Å	µ = 0.68 mm^−1
β = 109.066 (1)°	T = 100 K
V = 2840.14 (9) Å^3	Prism, colourless
Z = 8	0.46 × 0.17 × 0.15 mm

Data collection

Bruker D8 Venture diffractometer	2786 independent reflections
Radiation source: Microsource IuS Incoatec 3.0	2596 reflections with I > 2σ(I)
Double Bounce Multilayer Mirrors monochromator	Rint = 0.025
Detector resolution: 7.9 pixels mm^-1	θmax = 72.2°, θmin = 3.7°
φ and ω scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −7→6
Tmin = 0.646, Tmax = 0.754	l = −25→25
14321 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 2.0674P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2786 reflections	Δρmax = 0.24 e Å^−3
195 parameters	Δρmin = −0.18 e Å^−3
0 restraints

Special details

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. All C-H hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms (1.5xUeqiv for methyl groups). The H atom attached to nitrogen N1 was located in Fourier diff map and assigned Uiso = 1.2xUeqiv.

The X-ray intensity data for each chalcone derivative was measured at 100 K on a Bruker Photon II D8 Venture diffractometer equipped with both IµS-Cu and IµS-Mo microfocus X-ray sources. The Cu K_α (λ = 1.54178 Å) source was used for all crystallographic investigations. Data sets were corrected for Lorentz and polarization effects as well as absorption. The criterion for observed reflections was I > 2σ(I). Lattice parameters were determined from least-squares analysis and reflection data. Empirical absorption corrections were applied using SADABS. Structures were solved by direct methods and refined by full-matrix least-squares analysis on F² using X-SEED equipped with SHELXT (Barbour, 2001; Sheldrick, 2015a). All non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F² using the SHELXL program (Sheldrick, 2015b).

Unit-cell projections were visualized with Mercury 2020.1 (Macrae et al., 2020), Hirshfeld analyses were executed with CrystalExplorer17.5 (Turner et al., 2017), while distance/angle measurements, as well as ORTEP images, were captured using OLEX2 (Dolomanov et al., 2009). Electrostatic potential calculations employed GAUSSIAN09 (Frisch et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.46820 (3)	0.81616 (14)	0.39168 (4)	0.0250 (2)
O2	0.72479 (3)	0.81750 (17)	0.64907 (4)	0.0312 (2)
N1	0.63056 (4)	0.88412 (16)	0.60966 (4)	0.0186 (2)
HN1	0.6047 (6)	0.979 (3)	0.6119 (7)	0.028*
C1	0.49200 (4)	0.62787 (19)	0.39523 (5)	0.0186 (2)
C2	0.46888 (4)	0.4432 (2)	0.34406 (5)	0.0206 (2)
H2	0.485316	0.293005	0.351190	0.025*
C3	0.42525 (4)	0.4852 (2)	0.28807 (5)	0.0197 (2)
H3	0.410823	0.638878	0.283304	0.024*
C4	0.54573 (4)	0.58199 (19)	0.45210 (5)	0.0172 (2)
C5	0.56419 (4)	0.74641 (19)	0.50440 (5)	0.0172 (2)
H5	0.542254	0.881225	0.503505	0.021*
C6	0.61438 (4)	0.71465 (19)	0.55778 (5)	0.0166 (2)
C7	0.64652 (4)	0.51542 (19)	0.55888 (5)	0.0188 (2)
H7	0.680734	0.491344	0.595127	0.023*
C8	0.62815 (5)	0.3539 (2)	0.50687 (6)	0.0212 (2)
H8	0.650112	0.219210	0.507728	0.025*
C9	0.57818 (4)	0.38495 (19)	0.45336 (5)	0.0199 (2)
H9	0.566228	0.272749	0.417923	0.024*
C10	0.39684 (4)	0.32381 (19)	0.23303 (5)	0.0181 (2)
C11	0.34430 (5)	0.38547 (19)	0.18694 (5)	0.0204 (2)
H15	0.327915	0.529786	0.192141	0.025*
C12	0.31589 (4)	0.2384 (2)	0.13378 (5)	0.0202 (2)
H14	0.279916	0.282282	0.103821	0.024*
C13	0.33906 (4)	0.02806 (19)	0.12351 (5)	0.0191 (2)
C14	0.39167 (4)	−0.03316 (19)	0.16940 (5)	0.0200 (2)
H12	0.408461	−0.175418	0.163221	0.024*
C15	0.41973 (4)	0.10988 (19)	0.22367 (5)	0.0193 (2)
H11	0.454871	0.062276	0.254867	0.023*
C16	0.68404 (4)	0.9267 (2)	0.65190 (5)	0.0192 (2)
C17	0.68940 (5)	1.1167 (2)	0.70315 (6)	0.0231 (3)
H17A	0.682174	1.053758	0.743465	0.035*
H17B	0.662072	1.239254	0.682788	0.035*
H17C	0.727444	1.181338	0.716695	0.035*
C18	0.30808 (5)	−0.1296 (2)	0.06553 (6)	0.0238 (3)
H18A	0.281767	−0.226556	0.079507	0.036*
H18B	0.335026	−0.228993	0.053528	0.036*
H18C	0.287275	−0.036090	0.025790	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (4)	0.0224 (4)	0.0252 (4)	0.0049 (3)	0.0002 (3)	−0.0060 (3)
O2	0.0169 (4)	0.0408 (5)	0.0333 (5)	0.0008 (4)	0.0047 (3)	−0.0127 (4)
N1	0.0164 (4)	0.0197 (5)	0.0187 (4)	0.0018 (4)	0.0043 (3)	−0.0025 (4)
C1	0.0178 (5)	0.0196 (5)	0.0190 (5)	−0.0002 (4)	0.0068 (4)	−0.0017 (4)
C2	0.0203 (5)	0.0182 (5)	0.0216 (5)	0.0006 (4)	0.0046 (4)	−0.0033 (4)
C3	0.0202 (5)	0.0179 (5)	0.0210 (5)	−0.0010 (4)	0.0066 (4)	−0.0019 (4)
C4	0.0167 (5)	0.0191 (5)	0.0168 (5)	−0.0012 (4)	0.0066 (4)	−0.0005 (4)
C5	0.0165 (5)	0.0168 (5)	0.0190 (5)	0.0015 (4)	0.0068 (4)	0.0000 (4)
C6	0.0171 (5)	0.0182 (5)	0.0159 (5)	−0.0023 (4)	0.0072 (4)	−0.0005 (4)
C7	0.0175 (5)	0.0210 (5)	0.0169 (5)	0.0019 (4)	0.0045 (4)	0.0032 (4)
C8	0.0225 (5)	0.0188 (5)	0.0228 (5)	0.0052 (4)	0.0080 (4)	0.0009 (4)
C9	0.0221 (5)	0.0196 (5)	0.0180 (5)	0.0007 (4)	0.0066 (4)	−0.0026 (4)
C10	0.0180 (5)	0.0192 (5)	0.0171 (5)	−0.0033 (4)	0.0057 (4)	−0.0013 (4)
C11	0.0218 (5)	0.0185 (5)	0.0208 (5)	0.0007 (4)	0.0068 (4)	−0.0001 (4)
C12	0.0182 (5)	0.0233 (6)	0.0173 (5)	−0.0027 (4)	0.0035 (4)	0.0005 (4)
C13	0.0218 (5)	0.0211 (6)	0.0167 (5)	−0.0073 (4)	0.0093 (4)	−0.0016 (4)
C14	0.0216 (5)	0.0185 (5)	0.0224 (5)	−0.0017 (4)	0.0107 (4)	−0.0022 (4)
C15	0.0162 (5)	0.0210 (6)	0.0204 (5)	−0.0007 (4)	0.0058 (4)	0.0000 (4)
C16	0.0174 (5)	0.0235 (6)	0.0160 (5)	−0.0025 (4)	0.0046 (4)	0.0008 (4)
C17	0.0207 (5)	0.0269 (6)	0.0204 (5)	−0.0031 (4)	0.0049 (4)	−0.0034 (4)
C18	0.0270 (6)	0.0259 (6)	0.0192 (5)	−0.0082 (5)	0.0084 (4)	−0.0051 (4)

Geometric parameters (Å, º)

O1—C1	1.2302 (14)	C9—H9	0.9500
O2—C16	1.2219 (14)	C10—C15	1.4010 (15)
N1—C16	1.3675 (13)	C10—C11	1.4011 (15)
N1—C6	1.4097 (14)	C11—C12	1.3880 (15)
N1—HN1	0.862 (16)	C11—H15	0.9500
C1—C2	1.4800 (15)	C12—C13	1.3917 (16)
C1—C4	1.4988 (14)	C12—H14	0.9500
C2—C3	1.3333 (15)	C13—C14	1.4003 (15)
C2—H2	0.9500	C13—C18	1.5044 (15)
C3—C10	1.4638 (14)	C14—C15	1.3865 (15)
C3—H3	0.9500	C14—H12	0.9500
C4—C9	1.3943 (15)	C15—H11	0.9500
C4—C5	1.3990 (15)	C16—C17	1.4997 (15)
C5—C6	1.3930 (14)	C17—H17A	0.9800
C5—H5	0.9500	C17—H17B	0.9800
C6—C7	1.4007 (15)	C17—H17C	0.9800
C7—C8	1.3835 (16)	C18—H18A	0.9800
C7—H7	0.9500	C18—H18B	0.9800
C8—C9	1.3903 (15)	C18—H18C	0.9800
C8—H8	0.9500
C16—N1—C6	126.20 (9)	C11—C10—C3	118.81 (10)
C16—N1—HN1	117.2 (10)	C12—C11—C10	120.86 (10)
C6—N1—HN1	116.3 (10)	C12—C11—H15	119.6
O1—C1—C2	121.41 (10)	C10—C11—H15	119.6
O1—C1—C4	119.99 (10)	C11—C12—C13	121.29 (10)
C2—C1—C4	118.60 (9)	C11—C12—H14	119.4
C3—C2—C1	120.78 (10)	C13—C12—H14	119.4
C3—C2—H2	119.6	C12—C13—C14	117.85 (10)
C1—C2—H2	119.6	C12—C13—C18	120.92 (10)
C2—C3—C10	128.03 (11)	C14—C13—C18	121.23 (10)
C2—C3—H3	116.0	C15—C14—C13	121.26 (10)
C10—C3—H3	116.0	C15—C14—H12	119.4
C9—C4—C5	119.49 (10)	C13—C14—H12	119.4
C9—C4—C1	122.13 (10)	C14—C15—C10	120.74 (10)
C5—C4—C1	118.37 (9)	C14—C15—H11	119.6
C6—C5—C4	120.74 (10)	C10—C15—H11	119.6
C6—C5—H5	119.6	O2—C16—N1	123.00 (10)
C4—C5—H5	119.6	O2—C16—C17	121.81 (10)
C5—C6—C7	119.39 (10)	N1—C16—C17	115.19 (9)
C5—C6—N1	118.36 (9)	C16—C17—H17A	109.5
C7—C6—N1	122.25 (9)	C16—C17—H17B	109.5
C8—C7—C6	119.60 (9)	H17A—C17—H17B	109.5
C8—C7—H7	120.2	C16—C17—H17C	109.5
C6—C7—H7	120.2	H17A—C17—H17C	109.5
C7—C8—C9	121.28 (10)	H17B—C17—H17C	109.5
C7—C8—H8	119.4	C13—C18—H18A	109.5
C9—C8—H8	119.4	C13—C18—H18B	109.5
C8—C9—C4	119.50 (10)	H18A—C18—H18B	109.5
C8—C9—H9	120.2	C13—C18—H18C	109.5
C4—C9—H9	120.2	H18A—C18—H18C	109.5
C15—C10—C11	117.97 (10)	H18B—C18—H18C	109.5
C15—C10—C3	123.22 (10)
O1—C1—C2—C3	8.13 (16)	C5—C4—C9—C8	0.53 (16)
C4—C1—C2—C3	−171.62 (10)	C1—C4—C9—C8	178.84 (10)
C1—C2—C3—C10	−179.22 (10)	C2—C3—C10—C15	−14.93 (17)
O1—C1—C4—C9	−171.19 (10)	C2—C3—C10—C11	165.48 (11)
C2—C1—C4—C9	8.57 (15)	C15—C10—C11—C12	0.12 (15)
O1—C1—C4—C5	7.14 (15)	C3—C10—C11—C12	179.73 (10)
C2—C1—C4—C5	−173.11 (9)	C10—C11—C12—C13	−1.50 (16)
C9—C4—C5—C6	−0.36 (15)	C11—C12—C13—C14	1.20 (15)
C1—C4—C5—C6	−178.73 (9)	C11—C12—C13—C18	−179.68 (10)
C4—C5—C6—C7	−0.07 (15)	C12—C13—C14—C15	0.46 (15)
C4—C5—C6—N1	−179.07 (9)	C18—C13—C14—C15	−178.65 (9)
C16—N1—C6—C5	−156.74 (10)	C13—C14—C15—C10	−1.84 (16)
C16—N1—C6—C7	24.29 (16)	C11—C10—C15—C14	1.52 (15)
C5—C6—C7—C8	0.33 (15)	C3—C10—C15—C14	−178.07 (10)
N1—C6—C7—C8	179.29 (9)	C6—N1—C16—O2	−0.32 (17)
C6—C7—C8—C9	−0.16 (16)	C6—N1—C16—C17	−179.59 (10)
C7—C8—C9—C4	−0.28 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1^i	0.862 (16)	2.165 (16)	3.0213 (12)	172.3 (14)
C7—H7···O2	0.95	2.28	2.8281 (14)	116

Symmetry code: (i) −x+1, −y+2, −z+1.