(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one acetone monosolvate

Prasath, R.; Sarveswari, S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813020217

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one acetone monosolvate

R. Prasath, S. Sarveswari, S. W. Ng and E. R. T. Tiekink

In the title solvate, C₂₉H₂₁ClN₂O₂·C₃H₆O, a prop-2-en-1-one bridge links two quinolinyl residues; the latter are almost perpendicular [dihedral angle = 78.27 (6)°]. The dihedral angle between the quinonyl ring system and its pendant phenyl group is 59.78 (8)°. A small twist in the bridging prop-2-en-1-one group is noted [O=C—C=C torsion angle = −10.6 (3)°]. In the crystal, a three-dimensional architecture arises as a result of C—H

O and π–π stacking [centroid–centroid distances = 3.5504 (12)–3.6623 (12) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813020217/hg5334sup1.cif Contains datablocks general, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813020217/hg5334Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813020217/hg5334Isup3.cml Supplementary material

CCDC reference: 961838

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.058
wR factor = 0.167
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      1.471
            Test value =      1.275

Author Response: The relatively high residual electron density peak is near the methoxy-O2 atom and is not in a chemically sensible position. The maximum and minimum residual electron density peaks of 1.47 and 0.46 e\%A^-3^, respectively, were located 0.85 \%A and 0.68 \%A from the O2 and Cl1 atoms, respectively.

DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.976
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.21
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       1.47 eA-3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C21     ..        5.9 su
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H29A   ..  H29A    ..       2.11 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT975_ALERT_2_C Positive Residual Density at 1.07A from O3     .       0.48 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        117

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The the title compound, (I), was investigated in connection with on-going studies of quinolinyl chalcones (Prasath et al., 2013a), motivated by their potential anti-bacterial, anti-fungal, anti-malarial and anti-cancer activity (Joshi et al., 2011).

The molecular structure of the quinolinyl derivative, (I), Fig. 1, comprises two quinolinyl residues connected by the ends of a prop-2-en-1-one bridge, in an almost perpendicular relationship; the dihedral angle between the quinolinyl residues is 78.27 (6)°. The phenyl ring is inclined with respect to the quinolinyl residue to which it is attached, forming a dihedral angle of 59.78 (8)°. The conformation about the ethylene bond [C18═C19 = 1.336 (3) Å] is E. A small twist in the bridging prop-2-en-1-one group is manifested in the O1—C17—C18—C19 torsion angle of -10.6 (3)°. An distinct conformation was reported recently for a related structure, namely (2E)-3-(6-chloro-2-methoxyquinolin-3-yl)-1-(2,4-dimethylquinolin-3 - y)prop-2-en-1-one (Prasath et al., 2013b) where the nitrogen atoms are approximately syn as opposed to approximately anti in (I).

In the crystal packing, the quinolinyl and acetone molecules are connected by C—H···O interactions, Table 1. Additional C—H···O contacts and a number of π—π interactions, involving pyridyl, a quinolinyl-C₆ ring and the phenyl group, connect molecules into a three-dimensional architecture [centroid···centroid distances = 3.5504 (12), 3.5747 (12) and 3.6623 (12) Å], Fig. 2.

Related literature top

For background details and the biological applications of quinolinyl derivatives, see: Joshi et al. (2011); Prasath et al. (2013a). For a related structure, see: Prasath et al. (2013b).

Experimental top

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (260 mg, 0.001 M) and 2,6-dichloroquinoline-3-carbaldehyde (230 mg, 0.001 M) in methanol (20 ml) containing potassium hydroxide (0.2 g) was stirred at room temperature for 12 h. The reaction mixture was then neutralized with dilute acetic acid and the resultant solid was filtered, dried and purified by column chromatography using ethyl acetate - hexane (3:1) mixture to afford compound. Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded blocks in 62% yield; M.pt: 366–368 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. View in projection down the c axis of the unit-cell contents of (I). The π—π and C—H···O interactions are shown as purple and orange dashed lines, respectively.

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one acetone monosolvate top

Crystal data top

C₂₉H₂₁ClN₂O₂·C₃H₆O	F(000) = 1096
M_r = 523.01	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4229 reflections
a = 17.1714 (3) Å	θ = 2.6–76.5°
b = 10.7099 (2) Å	µ = 1.58 mm⁻¹
c = 14.5248 (2) Å	T = 100 K
β = 100.021 (2)°	Prism, pale-yellow
V = 2630.42 (8) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5408 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4574 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 2.6°
ω scan	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→13
T_min = 0.665, T_max = 1.000	l = −18→11
11367 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0953P)² + 1.726P] where P = (F_o² + 2F_c²)/3
5408 reflections	(Δ/σ)_max < 0.001
346 parameters	Δρ_max = 1.47 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₉H₂₁ClN₂O₂·C₃H₆O	V = 2630.42 (8) Å³
M_r = 523.01	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 17.1714 (3) Å	µ = 1.58 mm⁻¹
b = 10.7099 (2) Å	T = 100 K
c = 14.5248 (2) Å	0.30 × 0.25 × 0.20 mm
β = 100.021 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5408 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	4574 reflections with I > 2σ(I)
T_min = 0.665, T_max = 1.000	R_int = 0.032
11367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.03	Δρ_max = 1.47 e Å⁻³
5408 reflections	Δρ_min = −0.46 e Å⁻³
346 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cl1	0.62921 (3)	0.12909 (5)	0.32316 (4)	0.03232 (17)
O1	0.22537 (9)	0.34889 (15)	0.74016 (10)	0.0264 (3)
O2	0.47465 (9)	0.10414 (17)	0.80988 (11)	0.0324 (4)
N1	0.12879 (10)	0.59002 (17)	0.50819 (13)	0.0258 (4)
N2	0.55712 (10)	0.06750 (17)	0.70334 (12)	0.0245 (4)
C1	0.08058 (12)	0.5228 (2)	0.44105 (14)	0.0235 (4)
C2	0.03155 (13)	0.5910 (2)	0.36971 (15)	0.0295 (5)
H2	0.0332	0.6797	0.3702	0.035*
C3	−0.01806 (14)	0.5301 (2)	0.30037 (15)	0.0338 (5)
H3	−0.0501	0.5767	0.2525	0.041*
C4	−0.02195 (13)	0.3989 (2)	0.29950 (15)	0.0314 (5)
H4	−0.0567	0.3575	0.2510	0.038*
C5	0.02415 (12)	0.3303 (2)	0.36832 (14)	0.0264 (4)
H5	0.0204	0.2418	0.3677	0.032*
C6	0.07738 (11)	0.3911 (2)	0.44037 (13)	0.0216 (4)
C7	0.12817 (11)	0.32582 (19)	0.51344 (13)	0.0201 (4)
C8	0.17507 (11)	0.39553 (19)	0.58093 (13)	0.0210 (4)
C9	0.17372 (12)	0.5289 (2)	0.57624 (14)	0.0241 (4)
C10	0.22557 (14)	0.6057 (2)	0.64860 (17)	0.0332 (5)
H10A	0.2229	0.6936	0.6293	0.050*
H10B	0.2803	0.5763	0.6551	0.050*
H10C	0.2074	0.5976	0.7087	0.050*
C11	0.12677 (11)	0.18704 (19)	0.51703 (13)	0.0211 (4)
C12	0.14436 (12)	0.1150 (2)	0.44272 (14)	0.0242 (4)
H12	0.1597	0.1550	0.3903	0.029*
C13	0.13946 (13)	−0.0141 (2)	0.44520 (16)	0.0293 (5)
H13	0.1517	−0.0619	0.3946	0.035*
C14	0.11663 (13)	−0.0742 (2)	0.52142 (17)	0.0317 (5)
H14	0.1125	−0.1627	0.5225	0.038*
C15	0.10015 (13)	−0.0036 (2)	0.59537 (16)	0.0305 (5)
H15	0.0852	−0.0440	0.6479	0.037*
C16	0.10515 (12)	0.1257 (2)	0.59373 (14)	0.0250 (4)
H16	0.0938	0.1729	0.6452	0.030*
C17	0.23238 (11)	0.33553 (18)	0.65850 (13)	0.0208 (4)
C18	0.29959 (11)	0.27093 (19)	0.62832 (13)	0.0217 (4)
H18	0.2965	0.2518	0.5639	0.026*
C19	0.36459 (11)	0.23825 (19)	0.68814 (14)	0.0223 (4)
H19	0.3649	0.2491	0.7531	0.027*
C20	0.43552 (11)	0.18660 (19)	0.65883 (13)	0.0218 (4)
C21	0.49258 (12)	0.11715 (19)	0.72277 (14)	0.0231 (4)
C22	0.57217 (11)	0.08240 (19)	0.61423 (14)	0.0221 (4)
C23	0.64121 (12)	0.0285 (2)	0.59056 (15)	0.0266 (4)
H23	0.6762	−0.0175	0.6360	0.032*
C24	0.65784 (12)	0.0425 (2)	0.50195 (16)	0.0273 (4)
H24	0.7041	0.0059	0.4861	0.033*
C25	0.60641 (12)	0.1109 (2)	0.43496 (15)	0.0244 (4)
C26	0.53820 (12)	0.16319 (19)	0.45448 (14)	0.0229 (4)
H26	0.5035	0.2075	0.4076	0.027*
C27	0.52045 (11)	0.15016 (18)	0.54522 (14)	0.0204 (4)
C28	0.45154 (11)	0.20257 (19)	0.57037 (14)	0.0215 (4)
H28	0.4161	0.2491	0.5257	0.026*
C29	0.52882 (18)	0.0347 (3)	0.87429 (17)	0.0424 (6)
H29A	0.5101	0.0305	0.9342	0.064*
H29B	0.5807	0.0753	0.8832	0.064*
H29C	0.5332	−0.0500	0.8501	0.064*
O3	0.33767 (14)	0.4389 (2)	0.45197 (14)	0.0573 (6)
C30	0.23862 (15)	0.4489 (3)	0.31684 (17)	0.0373 (6)
H30A	0.2371	0.3579	0.3235	0.056*
H30B	0.2551	0.4700	0.2574	0.056*
H30C	0.1859	0.4835	0.3178	0.056*
C31	0.29599 (14)	0.5025 (2)	0.39548 (15)	0.0331 (5)
C32	0.29821 (18)	0.6428 (3)	0.40126 (19)	0.0450 (6)
H32A	0.3467	0.6692	0.4427	0.068*
H32B	0.2521	0.6728	0.4262	0.068*
H32C	0.2973	0.6777	0.3387	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0329 (3)	0.0336 (3)	0.0345 (3)	−0.0039 (2)	0.0173 (2)	−0.0023 (2)
O1	0.0261 (7)	0.0297 (8)	0.0242 (7)	0.0027 (6)	0.0063 (6)	−0.0013 (6)
O2	0.0278 (8)	0.0422 (10)	0.0265 (7)	0.0063 (7)	0.0026 (6)	−0.0116 (7)
N1	0.0244 (9)	0.0217 (9)	0.0326 (9)	0.0024 (7)	0.0087 (7)	0.0035 (7)
N2	0.0223 (8)	0.0263 (9)	0.0231 (8)	0.0029 (7)	−0.0008 (6)	−0.0031 (7)
C1	0.0213 (9)	0.0268 (11)	0.0245 (9)	0.0063 (8)	0.0098 (8)	0.0045 (8)
C2	0.0300 (11)	0.0297 (11)	0.0310 (11)	0.0103 (9)	0.0111 (9)	0.0089 (9)
C3	0.0296 (11)	0.0444 (14)	0.0279 (11)	0.0145 (10)	0.0063 (9)	0.0108 (10)
C4	0.0242 (10)	0.0431 (14)	0.0261 (10)	0.0082 (9)	0.0015 (8)	0.0005 (9)
C5	0.0235 (10)	0.0299 (11)	0.0261 (10)	0.0042 (8)	0.0054 (8)	0.0003 (8)
C6	0.0179 (9)	0.0264 (10)	0.0219 (9)	0.0040 (7)	0.0077 (7)	0.0031 (8)
C7	0.0148 (8)	0.0252 (10)	0.0216 (9)	0.0019 (7)	0.0064 (7)	0.0016 (7)
C8	0.0174 (9)	0.0247 (10)	0.0223 (9)	0.0019 (7)	0.0076 (7)	0.0015 (7)
C9	0.0201 (9)	0.0241 (10)	0.0294 (10)	0.0019 (8)	0.0077 (8)	0.0000 (8)
C10	0.0317 (11)	0.0225 (11)	0.0431 (13)	−0.0013 (9)	−0.0003 (10)	−0.0022 (9)
C11	0.0166 (8)	0.0224 (10)	0.0236 (9)	0.0024 (7)	0.0014 (7)	0.0009 (7)
C12	0.0195 (9)	0.0292 (11)	0.0229 (9)	0.0028 (8)	0.0008 (7)	−0.0024 (8)
C13	0.0229 (10)	0.0287 (11)	0.0330 (11)	0.0050 (8)	−0.0046 (8)	−0.0090 (9)
C14	0.0270 (10)	0.0205 (10)	0.0433 (12)	0.0009 (8)	−0.0062 (9)	−0.0008 (9)
C15	0.0251 (10)	0.0287 (11)	0.0358 (11)	−0.0027 (8)	0.0005 (9)	0.0065 (9)
C16	0.0218 (9)	0.0275 (11)	0.0250 (10)	−0.0002 (8)	0.0025 (7)	0.0014 (8)
C17	0.0184 (9)	0.0201 (9)	0.0238 (9)	−0.0013 (7)	0.0035 (7)	−0.0010 (7)
C18	0.0199 (9)	0.0231 (10)	0.0227 (9)	0.0012 (7)	0.0052 (7)	−0.0035 (7)
C19	0.0209 (9)	0.0242 (10)	0.0217 (9)	0.0002 (7)	0.0034 (7)	−0.0025 (7)
C20	0.0178 (9)	0.0225 (10)	0.0242 (9)	−0.0005 (7)	0.0011 (7)	−0.0042 (8)
C21	0.0247 (10)	0.0232 (10)	0.0202 (9)	−0.0008 (8)	0.0009 (7)	−0.0032 (7)
C22	0.0185 (9)	0.0192 (9)	0.0276 (10)	−0.0018 (7)	0.0007 (7)	−0.0035 (8)
C23	0.0177 (9)	0.0264 (10)	0.0341 (11)	0.0010 (8)	−0.0001 (8)	−0.0045 (9)
C24	0.0174 (9)	0.0273 (11)	0.0371 (11)	−0.0012 (8)	0.0047 (8)	−0.0076 (9)
C25	0.0218 (9)	0.0240 (10)	0.0294 (10)	−0.0055 (8)	0.0097 (8)	−0.0040 (8)
C26	0.0219 (9)	0.0199 (10)	0.0268 (10)	−0.0022 (7)	0.0039 (7)	−0.0002 (8)
C27	0.0169 (9)	0.0179 (9)	0.0261 (9)	−0.0012 (7)	0.0028 (7)	−0.0021 (7)
C28	0.0175 (9)	0.0208 (9)	0.0255 (9)	−0.0006 (7)	0.0019 (7)	−0.0015 (7)
C29	0.0550 (16)	0.0437 (15)	0.0290 (12)	0.0158 (12)	0.0087 (11)	0.0058 (10)
O3	0.0579 (13)	0.0665 (15)	0.0453 (11)	0.0049 (11)	0.0028 (10)	0.0181 (10)
C30	0.0363 (12)	0.0427 (14)	0.0359 (12)	−0.0130 (10)	0.0146 (10)	−0.0117 (10)
C31	0.0324 (12)	0.0415 (14)	0.0269 (10)	−0.0060 (10)	0.0098 (9)	0.0035 (9)
C32	0.0560 (17)	0.0404 (15)	0.0407 (13)	−0.0156 (12)	0.0142 (12)	−0.0066 (11)

Geometric parameters (Å, º) top

Cl1—C25	1.746 (2)	C14—H14	0.9500
O1—C17	1.221 (2)	C15—C16	1.388 (3)
O2—C21	1.360 (3)	C15—H15	0.9500
O2—C29	1.411 (3)	C16—H16	0.9500
N1—C9	1.317 (3)	C17—C18	1.476 (3)
N1—C1	1.369 (3)	C18—C19	1.336 (3)
N2—C21	1.304 (3)	C18—H18	0.9500
N2—C22	1.373 (3)	C19—C20	1.467 (3)
C1—C6	1.411 (3)	C19—H19	0.9500
C1—C2	1.419 (3)	C20—C28	1.371 (3)
C2—C3	1.366 (3)	C20—C21	1.435 (3)
C2—H2	0.9500	C22—C23	1.414 (3)
C3—C4	1.407 (4)	C22—C27	1.418 (3)
C3—H3	0.9500	C23—C24	1.374 (3)
C4—C5	1.375 (3)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.401 (3)
C5—C6	1.422 (3)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.372 (3)
C6—C7	1.433 (3)	C26—C27	1.410 (3)
C7—C8	1.375 (3)	C26—H26	0.9500
C7—C11	1.488 (3)	C27—C28	1.414 (3)
C8—C9	1.431 (3)	C28—H28	0.9500
C8—C17	1.505 (3)	C29—H29A	0.9800
C9—C10	1.499 (3)	C29—H29B	0.9800
C10—H10A	0.9800	C29—H29C	0.9800
C10—H10B	0.9800	O3—C31	1.202 (3)
C10—H10C	0.9800	C30—C31	1.488 (3)
C11—C16	1.398 (3)	C30—H30A	0.9800
C11—C12	1.401 (3)	C30—H30B	0.9800
C12—C13	1.386 (3)	C30—H30C	0.9800
C12—H12	0.9500	C31—C32	1.505 (4)
C13—C14	1.395 (3)	C32—H32A	0.9800
C13—H13	0.9500	C32—H32B	0.9800
C14—C15	1.383 (3)	C32—H32C	0.9800

C21—O2—C29	116.16 (17)	C18—C17—C8	114.89 (16)
C9—N1—C1	118.42 (19)	C19—C18—C17	122.50 (18)
C21—N2—C22	117.61 (17)	C19—C18—H18	118.7
N1—C1—C6	123.29 (18)	C17—C18—H18	118.7
N1—C1—C2	117.2 (2)	C18—C19—C20	123.50 (18)
C6—C1—C2	119.5 (2)	C18—C19—H19	118.3
C3—C2—C1	120.5 (2)	C20—C19—H19	118.3
C3—C2—H2	119.8	C28—C20—C21	116.46 (18)
C1—C2—H2	119.8	C28—C20—C19	122.50 (18)
C2—C3—C4	120.4 (2)	C21—C20—C19	121.03 (18)
C2—C3—H3	119.8	N2—C21—O2	119.87 (18)
C4—C3—H3	119.8	N2—C21—C20	125.56 (18)
C5—C4—C3	120.5 (2)	O2—C21—C20	114.56 (18)
C5—C4—H4	119.8	N2—C22—C23	119.04 (18)
C3—C4—H4	119.8	N2—C22—C27	121.91 (18)
C4—C5—C6	120.3 (2)	C23—C22—C27	119.06 (19)
C4—C5—H5	119.8	C24—C23—C22	120.2 (2)
C6—C5—H5	119.8	C24—C23—H23	119.9
C1—C6—C5	118.83 (18)	C22—C23—H23	119.9
C1—C6—C7	117.66 (18)	C23—C24—C25	119.92 (19)
C5—C6—C7	123.51 (19)	C23—C24—H24	120.0
C8—C7—C6	117.93 (19)	C25—C24—H24	120.0
C8—C7—C11	121.90 (17)	C26—C25—C24	121.83 (19)
C6—C7—C11	120.12 (17)	C26—C25—Cl1	118.97 (17)
C7—C8—C9	120.37 (18)	C24—C25—Cl1	119.20 (16)
C7—C8—C17	121.82 (18)	C25—C26—C27	118.94 (19)
C9—C8—C17	117.72 (18)	C25—C26—H26	120.5
N1—C9—C8	122.29 (19)	C27—C26—H26	120.5
N1—C9—C10	116.9 (2)	C26—C27—C28	121.92 (18)
C8—C9—C10	120.79 (19)	C26—C27—C22	120.04 (18)
C9—C10—H10A	109.5	C28—C27—C22	118.04 (18)
C9—C10—H10B	109.5	C20—C28—C27	120.41 (18)
H10A—C10—H10B	109.5	C20—C28—H28	119.8
C9—C10—H10C	109.5	C27—C28—H28	119.8
H10A—C10—H10C	109.5	O2—C29—H29A	109.5
H10B—C10—H10C	109.5	O2—C29—H29B	109.5
C16—C11—C12	118.5 (2)	H29A—C29—H29B	109.5
C16—C11—C7	120.37 (18)	O2—C29—H29C	109.5
C12—C11—C7	121.04 (18)	H29A—C29—H29C	109.5
C13—C12—C11	120.4 (2)	H29B—C29—H29C	109.5
C13—C12—H12	119.8	C31—C30—H30A	109.5
C11—C12—H12	119.8	C31—C30—H30B	109.5
C12—C13—C14	120.5 (2)	H30A—C30—H30B	109.5
C12—C13—H13	119.7	C31—C30—H30C	109.5
C14—C13—H13	119.7	H30A—C30—H30C	109.5
C15—C14—C13	119.2 (2)	H30B—C30—H30C	109.5
C15—C14—H14	120.4	O3—C31—C30	122.8 (3)
C13—C14—H14	120.4	O3—C31—C32	121.4 (2)
C14—C15—C16	120.7 (2)	C30—C31—C32	115.8 (2)
C14—C15—H15	119.6	C31—C32—H32A	109.5
C16—C15—H15	119.6	C31—C32—H32B	109.5
C15—C16—C11	120.6 (2)	H32A—C32—H32B	109.5
C15—C16—H16	119.7	C31—C32—H32C	109.5
C11—C16—H16	119.7	H32A—C32—H32C	109.5
O1—C17—C18	123.90 (18)	H32B—C32—H32C	109.5
O1—C17—C8	120.99 (18)

C9—N1—C1—C6	−0.9 (3)	C7—C11—C16—C15	176.94 (18)
C9—N1—C1—C2	178.66 (18)	C7—C8—C17—O1	−117.8 (2)
N1—C1—C2—C3	179.97 (19)	C9—C8—C17—O1	65.6 (3)
C6—C1—C2—C3	−0.5 (3)	C7—C8—C17—C18	67.3 (2)
C1—C2—C3—C4	0.8 (3)	C9—C8—C17—C18	−109.3 (2)
C2—C3—C4—C5	−0.1 (3)	O1—C17—C18—C19	−10.6 (3)
C3—C4—C5—C6	−1.1 (3)	C8—C17—C18—C19	164.11 (19)
N1—C1—C6—C5	178.86 (18)	C17—C18—C19—C20	−173.03 (19)
C2—C1—C6—C5	−0.7 (3)	C18—C19—C20—C28	20.8 (3)
N1—C1—C6—C7	−0.8 (3)	C18—C19—C20—C21	−159.9 (2)
C2—C1—C6—C7	179.69 (18)	C22—N2—C21—O2	179.46 (18)
C4—C5—C6—C1	1.5 (3)	C22—N2—C21—C20	−0.1 (3)
C4—C5—C6—C7	−178.94 (19)	C29—O2—C21—N2	−0.5 (3)
C1—C6—C7—C8	1.8 (3)	C29—O2—C21—C20	179.0 (2)
C5—C6—C7—C8	−177.81 (18)	C28—C20—C21—N2	−0.8 (3)
C1—C6—C7—C11	179.30 (17)	C19—C20—C21—N2	179.8 (2)
C5—C6—C7—C11	−0.3 (3)	C28—C20—C21—O2	179.62 (18)
C6—C7—C8—C9	−1.3 (3)	C19—C20—C21—O2	0.3 (3)
C11—C7—C8—C9	−178.73 (17)	C21—N2—C22—C23	−179.30 (19)
C6—C7—C8—C17	−177.82 (17)	C21—N2—C22—C27	0.6 (3)
C11—C7—C8—C17	4.7 (3)	N2—C22—C23—C24	−179.71 (19)
C1—N1—C9—C8	1.5 (3)	C27—C22—C23—C24	0.3 (3)
C1—N1—C9—C10	−179.85 (19)	C22—C23—C24—C25	0.3 (3)
C7—C8—C9—N1	−0.4 (3)	C23—C24—C25—C26	−1.3 (3)
C17—C8—C9—N1	176.27 (18)	C23—C24—C25—Cl1	179.27 (16)
C7—C8—C9—C10	−179.01 (19)	C24—C25—C26—C27	1.6 (3)
C17—C8—C9—C10	−2.3 (3)	Cl1—C25—C26—C27	−179.00 (15)
C8—C7—C11—C16	59.1 (3)	C25—C26—C27—C28	179.44 (18)
C6—C7—C11—C16	−118.3 (2)	C25—C26—C27—C22	−0.9 (3)
C8—C7—C11—C12	−123.1 (2)	N2—C22—C27—C26	179.99 (18)
C6—C7—C11—C12	59.5 (3)	C23—C22—C27—C26	−0.1 (3)
C16—C11—C12—C13	0.7 (3)	N2—C22—C27—C28	−0.3 (3)
C7—C11—C12—C13	−177.16 (18)	C23—C22—C27—C28	179.64 (18)
C11—C12—C13—C14	0.3 (3)	C21—C20—C28—C27	1.1 (3)
C12—C13—C14—C15	−1.0 (3)	C19—C20—C28—C27	−179.53 (18)
C13—C14—C15—C16	0.8 (3)	C26—C27—C28—C20	179.06 (19)
C14—C15—C16—C11	0.2 (3)	C22—C27—C28—C20	−0.6 (3)
C12—C11—C16—C15	−0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2ⁱ	0.95	2.47	3.319 (3)	149
C30—H30A···O1ⁱ	0.98	2.52	3.373 (4)	146
C28—H28···O3	0.95	2.57	3.467 (3)	158

Symmetry code: (i) x, −y+1/2, z−1/2.