5-(4-Methyl­benzo­yl)-4-(4-methyl­phen­yl)-1-[(1-phenyl­ethyl­idene)amino]pyrimidin-2(1H)-one

Mol­ecules of the title compound, C₂₇H₂₃N₃O₂, contain four rings that are not coplanar and the pyrimidine ring is slightly distorted from planarity. The dihedral angles between pairs of benzene rings are 88.6 (1), 88.6 (1) and 62.9 (1)°. The three benzene rings form dihedral angles of 55.3 (1), 36.2 (1) and 65.5 (1)° with the pyrimidine ring.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.137
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.19 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.11 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      94.00 A   3 

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-(4-Methylbenzoyl)-4-(4-methylphenyl)-1-[(1-phenylethylidene)amino]pyrimidin- 2(1H)-one

Crystal data

C27H23N3O2	F(000) = 888
Mr = 421.48	Dx = 1.185 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37167 reflections
a = 13.6001 (7) Å	θ = 2.0–27.6°
b = 17.1608 (10) Å	µ = 0.08 mm^−1
c = 10.8703 (5) Å	T = 296 K
β = 111.351 (4)°	Plate, colourless
V = 2362.9 (2) Å^3	0.65 × 0.45 × 0.21 mm
Z = 4

Data collection

Stoe IPDSII diffractometer	3269 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.049
Plane graphite monochromator	θmax = 26.0°, θmin = 2.0°
Detector resolution: 6.67 pixels mm^-1	h = −16→16
ω scans	k = −21→21
29539 measured reflections	l = −13→13
4639 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0774P)^2 + 0.1415P] where P = (Fo^2 + 2Fc^2)/3
4639 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. IR (KBr) ν (cm^-1): 3050–3036 (aromatic C—H), 2911 (aliphatic C—H), 1695 (s), 1650 (s, C═O), 1602–1573 (C═C and C═N). ¹H NMR (DMSO): δ 8.25 (s, 1H at C6), 7.97–7.02 (m, 13H, ArH), 2.35, 2.30, 2.26 (s, 9H, 3 × CH₃). Analysis calculated for C₂₇H₂₃N₃O₂: C 76.93, H 5.49, N 9.96%; found: C 76.87, H 5.71, N 9.81%.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.73143 (12)	0.29963 (9)	0.82542 (13)	0.0743 (5)
O2	0.42370 (10)	0.30815 (9)	0.25890 (13)	0.0690 (5)
N1	0.84218 (11)	0.32442 (9)	0.66503 (16)	0.0588 (5)
N2	0.72960 (11)	0.32175 (8)	0.61895 (13)	0.0506 (5)
N3	0.57722 (12)	0.34296 (9)	0.66902 (13)	0.0517 (5)
C1	1.00573 (15)	0.26398 (12)	0.73428 (19)	0.0634 (7)
C2	1.05734 (19)	0.31927 (18)	0.8242 (3)	0.0941 (10)
C3	1.1690 (2)	0.3225 (2)	0.8707 (3)	0.1157 (13)
C4	1.2233 (2)	0.2727 (2)	0.8226 (3)	0.1038 (13)
C5	1.1734 (2)	0.2196 (2)	0.7335 (4)	0.1036 (11)
C6	1.06542 (19)	0.21367 (17)	0.6894 (3)	0.0891 (10)
C7	0.88885 (14)	0.25903 (11)	0.68336 (17)	0.0541 (6)
C8	0.83659 (18)	0.18191 (13)	0.6575 (3)	0.0829 (9)
C9	0.68015 (15)	0.31939 (10)	0.71185 (17)	0.0536 (6)
C10	0.52343 (13)	0.35652 (9)	0.54317 (15)	0.0448 (5)
C11	0.56895 (13)	0.34663 (9)	0.44446 (15)	0.0452 (5)
C12	0.67479 (13)	0.33297 (10)	0.49017 (16)	0.0494 (5)
C13	0.41487 (13)	0.38656 (9)	0.51043 (15)	0.0451 (5)
C14	0.35261 (14)	0.35995 (10)	0.57832 (17)	0.0528 (6)
C15	0.25187 (15)	0.38820 (12)	0.54846 (19)	0.0607 (7)
C16	0.21038 (15)	0.44447 (11)	0.4526 (2)	0.0609 (7)
C17	0.27328 (15)	0.47225 (11)	0.38684 (18)	0.0569 (6)
C18	0.37392 (14)	0.44354 (10)	0.41482 (16)	0.0502 (5)
C19	0.0994 (2)	0.47447 (17)	0.4195 (3)	0.0979 (10)
C20	0.50751 (13)	0.34256 (10)	0.29991 (16)	0.0491 (5)
C21	0.55200 (13)	0.37950 (10)	0.20805 (15)	0.0481 (5)
C22	0.52194 (14)	0.35137 (11)	0.07931 (16)	0.0534 (5)
C23	0.56017 (16)	0.38517 (12)	−0.00857 (16)	0.0588 (6)
C24	0.62756 (16)	0.44856 (11)	0.02730 (17)	0.0582 (6)
C25	0.65497 (16)	0.47764 (11)	0.15448 (17)	0.0588 (6)
C26	0.61857 (14)	0.44340 (11)	0.24421 (16)	0.0541 (6)
C27	0.6706 (2)	0.48465 (14)	−0.0689 (2)	0.0796 (9)
H2	1.01970	0.35460	0.85490	0.1130*
H3	1.20510	0.35890	0.93440	0.1390*
H4	1.29660	0.27580	0.85240	0.1250*
H5	1.21170	0.18610	0.70060	0.1240*
H6	1.03160	0.17520	0.62840	0.1070*
H8A	0.76410	0.18760	0.64870	0.1240*
H8B	0.87190	0.14740	0.72970	0.1240*
H8C	0.83990	0.16070	0.57740	0.1240*
H12	0.70970	0.33140	0.43080	0.0590*
H14	0.37910	0.32280	0.64440	0.0630*
H15	0.21080	0.36900	0.59380	0.0730*
H17	0.24740	0.51080	0.32290	0.0680*
H18	0.41480	0.46260	0.36900	0.0600*
H19A	0.05140	0.43130	0.40230	0.1470*
H19B	0.08050	0.50710	0.34260	0.1470*
H19C	0.09560	0.50410	0.49250	0.1470*
H22	0.47570	0.30940	0.05280	0.0640*
H23	0.54050	0.36520	−0.09370	0.0710*
H25	0.69870	0.52100	0.17950	0.0710*
H26	0.63880	0.46320	0.32950	0.0650*
H27A	0.74480	0.47380	−0.04130	0.1190*
H27B	0.65990	0.54000	−0.07140	0.1190*
H27C	0.63470	0.46320	−0.15520	0.1190*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0700 (9)	0.0952 (11)	0.0530 (7)	0.0103 (8)	0.0169 (6)	0.0155 (7)
O2	0.0554 (8)	0.0908 (10)	0.0647 (8)	−0.0206 (7)	0.0265 (6)	−0.0277 (7)
N1	0.0434 (8)	0.0594 (9)	0.0690 (9)	−0.0035 (7)	0.0149 (7)	0.0027 (7)
N2	0.0445 (8)	0.0525 (8)	0.0544 (8)	0.0012 (6)	0.0177 (6)	0.0024 (6)
N3	0.0549 (9)	0.0565 (8)	0.0467 (7)	0.0008 (7)	0.0220 (6)	0.0017 (6)
C1	0.0479 (10)	0.0754 (13)	0.0621 (11)	0.0009 (9)	0.0143 (8)	0.0167 (9)
C2	0.0607 (13)	0.124 (2)	0.0895 (16)	−0.0222 (14)	0.0177 (12)	−0.0187 (15)
C3	0.0757 (19)	0.161 (3)	0.0949 (19)	−0.038 (2)	0.0125 (15)	−0.013 (2)
C4	0.0561 (15)	0.147 (3)	0.101 (2)	0.0081 (18)	0.0200 (15)	0.050 (2)
C5	0.0632 (15)	0.121 (2)	0.130 (2)	0.0244 (16)	0.0393 (16)	0.037 (2)
C6	0.0619 (14)	0.0933 (17)	0.1104 (19)	0.0163 (12)	0.0293 (13)	0.0111 (14)
C7	0.0487 (10)	0.0588 (11)	0.0515 (9)	0.0007 (8)	0.0143 (7)	0.0031 (8)
C8	0.0605 (13)	0.0597 (12)	0.1163 (19)	−0.0006 (10)	0.0175 (12)	−0.0056 (12)
C9	0.0569 (10)	0.0549 (10)	0.0504 (9)	0.0010 (8)	0.0211 (8)	0.0043 (7)
C10	0.0501 (9)	0.0406 (8)	0.0470 (8)	−0.0032 (7)	0.0217 (7)	−0.0017 (6)
C11	0.0454 (9)	0.0470 (8)	0.0467 (8)	−0.0019 (7)	0.0208 (7)	−0.0033 (7)
C12	0.0519 (10)	0.0510 (9)	0.0493 (9)	−0.0026 (8)	0.0233 (7)	−0.0055 (7)
C13	0.0496 (9)	0.0439 (8)	0.0458 (8)	−0.0025 (7)	0.0221 (7)	−0.0048 (6)
C14	0.0563 (10)	0.0548 (10)	0.0550 (9)	0.0005 (8)	0.0294 (8)	0.0019 (8)
C15	0.0610 (11)	0.0636 (11)	0.0718 (12)	−0.0033 (9)	0.0414 (9)	−0.0030 (9)
C16	0.0523 (11)	0.0578 (11)	0.0769 (12)	0.0017 (8)	0.0287 (9)	−0.0058 (9)
C17	0.0586 (11)	0.0493 (9)	0.0630 (10)	0.0047 (8)	0.0225 (9)	0.0024 (8)
C18	0.0543 (10)	0.0498 (9)	0.0516 (9)	−0.0012 (8)	0.0253 (8)	−0.0002 (7)
C19	0.0656 (14)	0.0984 (18)	0.138 (2)	0.0190 (13)	0.0469 (15)	0.0116 (17)
C20	0.0447 (9)	0.0546 (9)	0.0504 (9)	−0.0006 (8)	0.0201 (7)	−0.0122 (7)
C21	0.0458 (9)	0.0556 (9)	0.0419 (8)	0.0058 (7)	0.0148 (7)	−0.0050 (7)
C22	0.0521 (10)	0.0588 (10)	0.0451 (8)	0.0066 (8)	0.0126 (7)	−0.0060 (7)
C23	0.0687 (12)	0.0666 (11)	0.0393 (8)	0.0149 (9)	0.0175 (8)	−0.0017 (8)
C24	0.0700 (12)	0.0595 (11)	0.0494 (9)	0.0193 (9)	0.0268 (8)	0.0104 (8)
C25	0.0695 (12)	0.0551 (10)	0.0549 (10)	−0.0014 (9)	0.0262 (9)	0.0001 (8)
C26	0.0622 (11)	0.0577 (10)	0.0429 (8)	−0.0012 (8)	0.0197 (8)	−0.0061 (7)
C27	0.1121 (19)	0.0744 (14)	0.0659 (12)	0.0112 (13)	0.0488 (12)	0.0147 (10)

Geometric parameters (Å, º)

O1—C9	1.224 (2)	C21—C26	1.385 (3)
O2—C20	1.215 (2)	C22—C23	1.372 (3)
N1—N2	1.428 (2)	C23—C24	1.384 (3)
N1—C7	1.269 (2)	C24—C25	1.387 (2)
N2—C9	1.403 (2)	C24—C27	1.505 (3)
N2—C12	1.339 (2)	C25—C26	1.376 (3)
N3—C9	1.366 (3)	C2—H2	0.9300
N3—C10	1.316 (2)	C3—H3	0.9300
C1—C2	1.360 (4)	C4—H4	0.9300
C1—C6	1.390 (4)	C5—H5	0.9300
C1—C7	1.483 (3)	C6—H6	0.9300
C2—C3	1.416 (4)	C8—H8A	0.9600
C3—C4	1.353 (4)	C8—H8B	0.9600
C4—C5	1.323 (5)	C8—H8C	0.9600
C5—C6	1.373 (4)	C12—H12	0.9300
C7—C8	1.480 (3)	C14—H14	0.9300
C10—C11	1.431 (2)	C15—H15	0.9300
C10—C13	1.480 (3)	C17—H17	0.9300
C11—C12	1.361 (3)	C18—H18	0.9300
C11—C20	1.489 (2)	C19—H19A	0.9600
C13—C14	1.388 (3)	C19—H19B	0.9600
C13—C18	1.387 (2)	C19—H19C	0.9600
C14—C15	1.376 (3)	C22—H22	0.9300
C15—C16	1.382 (3)	C23—H23	0.9300
C16—C17	1.384 (3)	C25—H25	0.9300
C16—C19	1.509 (4)	C26—H26	0.9300
C17—C18	1.380 (3)	C27—H27A	0.9600
C20—C21	1.485 (2)	C27—H27B	0.9600
C21—C22	1.394 (2)	C27—H27C	0.9600
O1···N1	2.721 (2)	C12···H26	2.7700
O1···C7	3.140 (3)	C15···H26^iv	3.0100
O1···C8	3.370 (3)	C16···H26^iv	2.9600
O1···C8^i	3.379 (3)	C17···H26^iv	3.0800
O1···C12^i	3.160 (2)	C20···H18	2.6600
O2···C18	3.093 (2)	C21···H27B^viii	3.0500
O2···C5^ii	3.348 (3)	C21···H12	2.7100
O2···C13	3.089 (2)	C22···H27B^viii	3.0700
O2···C4^ii	3.348 (3)	C23···H8A^iii	2.9500
O1···H12^i	2.5900	C24···H8A^iii	2.9800
O1···H8A	2.8600	C26···H12	2.7400
O1···H8C^i	2.6800	H2···N1	2.5900
O2···H22	2.5800	H3···H27B^ix	2.5700
O2···H4^ii	2.7200	H4···O2^vi	2.7200
O2···H5^ii	2.7200	H5···O2^vi	2.7200
O2···H14^iii	2.5300	H6···C8	2.7900
N1···O1	2.721 (2)	H6···H8C	2.4700
N1···H2	2.5900	H8A···O1	2.8600
N2···H8A	2.3500	H8A···N2	2.3500
N2···H17^iv	2.9300	H8A···C9	2.7300
N3···H14	2.6300	H8A···C12	3.0200
N3···H23^v	2.8300	H8A···C23^i	2.9500
N3···H27C^v	2.7300	H8A···C24^i	2.9800
C4···O2^vi	3.348 (3)	H8B···C6	3.0400
C4···C14^vi	3.527 (4)	H8C···C6	3.0000
C5···O2^vi	3.348 (3)	H8C···H6	2.4700
C7···O1	3.140 (3)	H8C···O1^iii	2.6800
C8···O1^iii	3.379 (3)	H12···C21	2.7100
C8···C24^i	3.488 (3)	H12···C26	2.7400
C8···O1	3.370 (3)	H12···H26	2.5500
C8···C9	3.370 (3)	H12···O1^iii	2.5900
C8···C12	3.458 (3)	H14···N3	2.6300
C9···C8	3.370 (3)	H14···O2^i	2.5300
C10···C22^i	3.590 (2)	H15···C4^x	2.9400
C12···C17^iv	3.574 (3)	H17···H19B	2.3600
C12···C8	3.458 (3)	H17···N2^iv	2.9300
C12···C26	3.136 (2)	H18···C11	2.7900
C12···O1^iii	3.160 (2)	H18···C20	2.6600
C13···O2	3.089 (2)	H18···H27C^viii	2.5200
C14···C4^ii	3.527 (4)	H19B···H17	2.3600
C17···C12^iv	3.574 (3)	H22···O2	2.5800
C18···O2	3.093 (2)	H22···C10^iii	2.9300
C18···C20	3.085 (3)	H23···N3^xi	2.8300
C20···C18	3.085 (3)	H23···H27C	2.3500
C22···C10^iii	3.590 (2)	H26···C11	2.7100
C24···C8^iii	3.488 (3)	H26···C12	2.7700
C26···C12	3.136 (2)	H26···H12	2.5500
C4···H15^vii	2.9400	H26···C15^iv	3.0100
C6···H8B	3.0400	H26···C16^iv	2.9600
C6···H8C	3.0000	H26···C17^iv	3.0800
C8···H6	2.7900	H27B···C21^viii	3.0500
C9···H8A	2.7300	H27B···C22^viii	3.0700
C9···H27C^v	3.0400	H27B···H3^ix	2.5700
C10···H22^i	2.9300	H27C···N3^xi	2.7300
C11···H26	2.7100	H27C···C9^xi	3.0400
C11···H18	2.7900	H27C···H23	2.3500
C12···H8A	3.0200	H27C···H18^viii	2.5200
N2—N1—C7	115.97 (15)	C21—C26—C25	120.25 (16)
N1—N2—C9	118.83 (14)	C1—C2—H2	120.00
N1—N2—C12	118.68 (15)	C3—C2—H2	120.00
C9—N2—C12	121.77 (16)	C2—C3—H3	120.00
C9—N3—C10	121.30 (16)	C4—C3—H3	120.00
C2—C1—C6	118.1 (2)	C3—C4—H4	120.00
C2—C1—C7	120.7 (2)	C5—C4—H4	120.00
C6—C1—C7	121.1 (2)	C4—C5—H5	120.00
C1—C2—C3	119.3 (3)	C6—C5—H5	120.00
C2—C3—C4	120.2 (3)	C1—C6—H6	119.00
C3—C4—C5	120.8 (3)	C5—C6—H6	119.00
C4—C5—C6	120.3 (3)	C7—C8—H8A	109.00
C1—C6—C5	121.3 (3)	C7—C8—H8B	109.00
N1—C7—C1	114.51 (17)	C7—C8—H8C	109.00
N1—C7—C8	125.66 (19)	H8A—C8—H8B	110.00
C1—C7—C8	119.83 (18)	H8A—C8—H8C	109.00
O1—C9—N2	119.18 (19)	H8B—C8—H8C	109.00
O1—C9—N3	124.24 (18)	N2—C12—H12	119.00
N2—C9—N3	116.52 (15)	C11—C12—H12	119.00
N3—C10—C11	122.01 (17)	C13—C14—H14	120.00
N3—C10—C13	116.10 (15)	C15—C14—H14	120.00
C11—C10—C13	121.82 (14)	C14—C15—H15	119.00
C10—C11—C12	115.81 (14)	C16—C15—H15	119.00
C10—C11—C20	124.56 (16)	C16—C17—H17	120.00
C12—C11—C20	119.33 (16)	C18—C17—H17	120.00
N2—C12—C11	121.24 (16)	C13—C18—H18	120.00
C10—C13—C14	120.40 (14)	C17—C18—H18	120.00
C10—C13—C18	121.26 (16)	C16—C19—H19A	109.00
C14—C13—C18	118.30 (17)	C16—C19—H19B	110.00
C13—C14—C15	120.44 (16)	C16—C19—H19C	110.00
C14—C15—C16	121.49 (19)	H19A—C19—H19B	109.00
C15—C16—C17	118.1 (2)	H19A—C19—H19C	109.00
C15—C16—C19	121.1 (2)	H19B—C19—H19C	109.00
C17—C16—C19	120.80 (19)	C21—C22—H22	120.00
C16—C17—C18	120.87 (17)	C23—C22—H22	120.00
C13—C18—C17	120.80 (17)	C22—C23—H23	120.00
O2—C20—C11	120.07 (16)	C24—C23—H23	119.00
O2—C20—C21	121.21 (15)	C24—C25—H25	119.00
C11—C20—C21	118.70 (15)	C26—C25—H25	119.00
C20—C21—C22	119.02 (16)	C21—C26—H26	120.00
C20—C21—C26	122.11 (14)	C25—C26—H26	120.00
C22—C21—C26	118.80 (16)	C24—C27—H27A	109.00
C21—C22—C23	120.40 (17)	C24—C27—H27B	109.00
C22—C23—C24	121.09 (16)	C24—C27—H27C	109.00
C23—C24—C25	118.28 (18)	H27A—C27—H27B	109.00
C23—C24—C27	120.86 (17)	H27A—C27—H27C	110.00
C25—C24—C27	120.87 (18)	H27B—C27—H27C	110.00
C24—C25—C26	121.16 (18)
C7—N1—N2—C9	89.55 (19)	N3—C10—C11—C12	−8.8 (2)
C7—N1—N2—C12	−100.04 (19)	C11—C10—C13—C18	−36.2 (2)
N2—N1—C7—C8	1.9 (3)	C20—C11—C12—N2	−167.50 (15)
N2—N1—C7—C1	−178.59 (15)	C10—C11—C20—O2	−38.8 (3)
N1—N2—C9—N3	158.60 (15)	C12—C11—C20—O2	134.71 (19)
C12—N2—C9—O1	171.17 (17)	C12—C11—C20—C21	−43.8 (2)
N1—N2—C9—O1	−18.7 (2)	C10—C11—C20—C21	142.72 (17)
C12—N2—C9—N3	−11.5 (2)	C10—C11—C12—N2	6.5 (2)
N1—N2—C12—C11	−166.69 (15)	C10—C13—C14—C15	179.61 (16)
C9—N2—C12—C11	3.4 (2)	C18—C13—C14—C15	1.7 (3)
C9—N3—C10—C13	−176.23 (15)	C10—C13—C18—C17	−178.73 (16)
C10—N3—C9—O1	−173.58 (17)	C14—C13—C18—C17	−0.8 (2)
C10—N3—C9—N2	9.3 (2)	C13—C14—C15—C16	−1.2 (3)
C9—N3—C10—C11	0.7 (3)	C14—C15—C16—C17	−0.2 (3)
C7—C1—C2—C3	−179.9 (2)	C14—C15—C16—C19	179.3 (2)
C2—C1—C6—C5	−0.4 (4)	C15—C16—C17—C18	1.1 (3)
C6—C1—C2—C3	−1.4 (4)	C19—C16—C17—C18	−178.5 (2)
C6—C1—C7—N1	−140.7 (2)	C16—C17—C18—C13	−0.6 (3)
C2—C1—C7—N1	37.8 (3)	O2—C20—C21—C22	−24.4 (3)
C7—C1—C6—C5	178.1 (3)	O2—C20—C21—C26	152.49 (19)
C6—C1—C7—C8	38.9 (3)	C11—C20—C21—C22	154.10 (17)
C2—C1—C7—C8	−142.7 (2)	C11—C20—C21—C26	−29.0 (3)
C1—C2—C3—C4	2.2 (5)	C20—C21—C22—C23	178.82 (18)
C2—C3—C4—C5	−1.2 (5)	C26—C21—C22—C23	1.8 (3)
C3—C4—C5—C6	−0.7 (5)	C20—C21—C26—C25	−177.61 (18)
C4—C5—C6—C1	1.5 (5)	C22—C21—C26—C25	−0.7 (3)
C13—C10—C11—C12	167.95 (15)	C21—C22—C23—C24	−1.2 (3)
C13—C10—C11—C20	−18.4 (2)	C22—C23—C24—C25	−0.5 (3)
N3—C10—C11—C20	164.89 (16)	C22—C23—C24—C27	179.1 (2)
N3—C10—C13—C18	140.76 (16)	C23—C24—C25—C26	1.7 (3)
C11—C10—C13—C14	145.99 (16)	C27—C24—C25—C26	−177.9 (2)
N3—C10—C13—C14	−37.1 (2)	C24—C25—C26—C21	−1.0 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1; (vi) x+1, −y+1/2, z+1/2; (vii) x+1, y, z; (viii) −x+1, −y+1, −z; (ix) −x+2, −y+1, −z+1; (x) x−1, y, z; (xi) x, y, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N2	0.96	2.35	2.758 (3)	105
C12—H12···O1^iii	0.93	2.59	3.160 (2)	120
C14—H14···O2^i	0.93	2.53	3.425 (2)	161

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