1-[(4-Methyl­benzyl­idene)amino]-5-(4-methyl­benzo­yl)-4-(p-tol­yl)pyrimidin-2(1H)-one

In the title mol­ecule, C₂₇H₂₃N₃O₂, the three benzene rings make dihedral angles of 84.4 (1), 36.6 (1) and 59.3 (1)° with the central pyrimidine ring. In the crystal structure, mol­ecules associate into centrosymmetric dimers via weak C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.112
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C9      ..       2.93 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

---

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).

1-[(4-Methylbenzylidene)amino]-5-(4-methylbenzoyl)-4-(p-tolyl)pyrimidin- 2(1H)-one

Crystal data

C27H23N3O2	F(000) = 888
Mr = 421.48	Dx = 1.244 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 36960 reflections
a = 13.9829 (7) Å	θ = 1.7–27.5°
b = 12.0458 (7) Å	µ = 0.08 mm^−1
c = 16.4807 (9) Å	T = 296 K
β = 125.831 (3)°	Prism, light yellow
V = 2250.6 (2) Å^3	0.54 × 0.38 × 0.19 mm
Z = 4

Data collection

Stoe IPDSII diffractometer	2996 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.112
Plane graphite monochromator	θmax = 26.0°, θmin = 1.8°
Detector resolution: 6.67 pixels mm^-1	h = −17→17
ω scans	k = −14→14
38085 measured reflections	l = −20→20
4427 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0712P)^2 + 0.1779P] where P = (Fo^2 + 2Fc^2)/3
4427 reflections	(Δ/σ)max < 0.001
296 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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	0.83702 (14)	0.52962 (14)	0.77686 (13)	0.0964 (6)
O2	0.31115 (13)	0.43154 (11)	0.46399 (10)	0.0808 (5)
N1	0.70988 (19)	0.71660 (15)	0.73973 (16)	0.0921 (8)
N2	0.65778 (15)	0.61179 (13)	0.69986 (13)	0.0737 (6)
N3	0.67485 (14)	0.41718 (13)	0.69967 (12)	0.0700 (6)
C1	0.80446 (17)	0.87115 (15)	0.73059 (16)	0.0673 (7)
C2	0.82939 (19)	0.92041 (16)	0.81681 (17)	0.0768 (8)
C3	0.8935 (2)	1.01676 (17)	0.85217 (19)	0.0852 (9)
C4	0.9354 (2)	1.06699 (17)	0.8031 (2)	0.0873 (9)
C5	0.9099 (3)	1.01813 (19)	0.7171 (2)	0.0992 (10)
C6	0.8454 (2)	0.92209 (17)	0.68063 (19)	0.0871 (9)
C7	1.0098 (3)	1.1714 (2)	0.8449 (3)	0.1307 (13)
C8	0.74362 (18)	0.76594 (15)	0.69431 (17)	0.0680 (7)
C9	0.73124 (19)	0.51760 (18)	0.72854 (16)	0.0745 (8)
C10	0.55917 (17)	0.40925 (15)	0.64304 (13)	0.0608 (6)
C11	0.48425 (17)	0.50454 (14)	0.60719 (14)	0.0616 (6)
C12	0.54069 (18)	0.60426 (16)	0.64085 (15)	0.0694 (7)
C13	0.51453 (16)	0.29315 (14)	0.62465 (13)	0.0619 (6)
C14	0.57616 (19)	0.20997 (16)	0.61578 (15)	0.0732 (7)
C15	0.5423 (2)	0.10006 (17)	0.60666 (17)	0.0828 (8)
C16	0.4469 (2)	0.07049 (17)	0.60663 (16)	0.0818 (8)
C17	0.3852 (2)	0.15362 (17)	0.61509 (16)	0.0787 (8)
C18	0.41847 (18)	0.26350 (16)	0.62445 (14)	0.0688 (7)
C19	0.4126 (3)	−0.0501 (2)	0.5999 (2)	0.1207 (13)
C20	0.35492 (17)	0.50393 (14)	0.52776 (14)	0.0638 (6)
C21	0.28178 (17)	0.59555 (14)	0.52506 (14)	0.0637 (6)
C22	0.18273 (18)	0.62947 (17)	0.43252 (15)	0.0755 (7)
C23	0.11351 (19)	0.71438 (18)	0.42675 (16)	0.0819 (7)
C24	0.13710 (19)	0.76731 (17)	0.51094 (17)	0.0786 (8)
C25	0.23406 (18)	0.73157 (16)	0.60310 (15)	0.0723 (7)
C26	0.30547 (17)	0.64737 (15)	0.61036 (14)	0.0656 (6)
C27	0.0613 (3)	0.8617 (2)	0.5031 (2)	0.1125 (11)
H2	0.80240	0.88780	0.85110	0.0920*
H3	0.90910	1.04890	0.91010	0.1020*
H5	0.93700	1.05090	0.68300	0.1190*
H6	0.82880	0.89080	0.62210	0.1050*
H7A	1.06600	1.17170	0.82920	0.1970*
H7B	1.05080	1.17310	0.91620	0.1970*
H7C	0.95980	1.23540	0.81580	0.1970*
H8	0.739 (2)	0.733 (2)	0.6410 (19)	0.103 (8)*
H12	0.49600	0.66890	0.62200	0.0830*
H14	0.64090	0.22810	0.61600	0.0880*
H15	0.58450	0.04530	0.60040	0.0990*
H17	0.32020	0.13530	0.61450	0.0940*
H18	0.37610	0.31810	0.63070	0.0830*
H19A	0.34740	−0.06700	0.53240	0.1810*
H19B	0.39030	−0.06340	0.64420	0.1810*
H19C	0.47840	−0.09660	0.61870	0.1810*
H22	0.16340	0.59450	0.37440	0.0910*
H23	0.04870	0.73690	0.36420	0.0980*
H25	0.25130	0.76500	0.66110	0.0870*
H26	0.37020	0.62500	0.67310	0.0790*
H27A	0.07530	0.92630	0.47730	0.1690*
H27B	0.08060	0.87790	0.56820	0.1690*
H27C	−0.02030	0.84110	0.45890	0.1690*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0687 (10)	0.1111 (12)	0.0943 (11)	−0.0210 (9)	0.0393 (9)	−0.0146 (9)
O2	0.0908 (10)	0.0668 (8)	0.0641 (8)	−0.0047 (7)	0.0337 (8)	−0.0119 (6)
N1	0.1126 (15)	0.0855 (12)	0.1021 (14)	−0.0467 (11)	0.0763 (13)	−0.0359 (10)
N2	0.0783 (11)	0.0692 (10)	0.0833 (11)	−0.0222 (8)	0.0528 (10)	−0.0169 (8)
N3	0.0680 (10)	0.0724 (10)	0.0701 (10)	−0.0080 (8)	0.0407 (9)	−0.0039 (8)
C1	0.0657 (11)	0.0560 (10)	0.0818 (13)	0.0013 (8)	0.0441 (10)	−0.0024 (9)
C2	0.0803 (13)	0.0693 (12)	0.0925 (15)	−0.0092 (10)	0.0572 (12)	−0.0126 (10)
C3	0.0881 (15)	0.0696 (12)	0.1035 (17)	−0.0106 (11)	0.0593 (14)	−0.0180 (11)
C4	0.0814 (14)	0.0616 (12)	0.118 (2)	−0.0069 (10)	0.0578 (14)	−0.0034 (12)
C5	0.130 (2)	0.0694 (13)	0.128 (2)	−0.0134 (14)	0.0923 (19)	−0.0005 (13)
C6	0.1151 (18)	0.0664 (12)	0.0984 (16)	−0.0070 (12)	0.0729 (15)	−0.0028 (11)
C7	0.133 (2)	0.0872 (18)	0.174 (3)	−0.0448 (17)	0.091 (2)	−0.0293 (18)
C8	0.0724 (12)	0.0583 (10)	0.0746 (13)	−0.0001 (9)	0.0437 (11)	−0.0045 (9)
C9	0.0707 (13)	0.0864 (14)	0.0689 (12)	−0.0149 (11)	0.0423 (11)	−0.0084 (10)
C10	0.0673 (11)	0.0640 (10)	0.0553 (10)	−0.0059 (8)	0.0383 (9)	−0.0026 (8)
C11	0.0712 (11)	0.0564 (10)	0.0625 (11)	−0.0071 (8)	0.0421 (10)	−0.0033 (8)
C12	0.0770 (13)	0.0634 (11)	0.0741 (12)	−0.0080 (9)	0.0478 (11)	−0.0040 (9)
C13	0.0687 (11)	0.0585 (10)	0.0583 (10)	−0.0036 (8)	0.0371 (9)	0.0001 (8)
C14	0.0768 (13)	0.0708 (12)	0.0746 (13)	−0.0013 (10)	0.0457 (11)	−0.0064 (9)
C15	0.1008 (16)	0.0639 (12)	0.0833 (14)	0.0064 (11)	0.0537 (13)	−0.0030 (10)
C16	0.1079 (17)	0.0642 (12)	0.0726 (13)	−0.0123 (11)	0.0524 (13)	−0.0027 (9)
C17	0.0895 (15)	0.0753 (13)	0.0768 (13)	−0.0175 (11)	0.0518 (12)	0.0002 (10)
C18	0.0767 (12)	0.0660 (11)	0.0700 (12)	−0.0039 (9)	0.0465 (10)	0.0028 (9)
C19	0.177 (3)	0.0683 (14)	0.125 (2)	−0.0283 (16)	0.093 (2)	−0.0078 (14)
C20	0.0744 (12)	0.0557 (10)	0.0580 (10)	−0.0069 (8)	0.0369 (10)	0.0003 (8)
C21	0.0660 (11)	0.0556 (10)	0.0602 (11)	−0.0056 (8)	0.0318 (9)	−0.0010 (8)
C22	0.0739 (13)	0.0729 (12)	0.0584 (11)	−0.0049 (10)	0.0267 (10)	−0.0033 (9)
C23	0.0728 (13)	0.0762 (13)	0.0656 (12)	0.0047 (10)	0.0230 (10)	0.0063 (10)
C24	0.0740 (13)	0.0682 (12)	0.0787 (14)	0.0073 (10)	0.0364 (11)	0.0070 (10)
C25	0.0730 (12)	0.0668 (11)	0.0672 (12)	0.0002 (9)	0.0355 (10)	−0.0030 (9)
C26	0.0634 (11)	0.0641 (11)	0.0557 (10)	0.0000 (8)	0.0272 (9)	0.0024 (8)
C27	0.107 (2)	0.1018 (18)	0.113 (2)	0.0366 (15)	0.0556 (17)	0.0137 (15)

Geometric parameters (Å, º)

O1—C9	1.210 (4)	C21—C26	1.389 (3)
O2—C20	1.219 (2)	C22—C23	1.373 (4)
N1—N2	1.413 (3)	C23—C24	1.380 (3)
N1—C8	1.245 (4)	C24—C25	1.386 (3)
N2—C9	1.413 (3)	C24—C27	1.508 (4)
N2—C12	1.331 (3)	C25—C26	1.379 (3)
N3—C9	1.368 (3)	C2—H2	0.9300
N3—C10	1.315 (3)	C3—H3	0.9300
C1—C2	1.383 (3)	C5—H5	0.9300
C1—C6	1.391 (4)	C6—H6	0.9300
C1—C8	1.446 (3)	C7—H7A	0.9600
C2—C3	1.371 (3)	C7—H7B	0.9600
C3—C4	1.385 (4)	C7—H7C	0.9600
C4—C5	1.375 (4)	C8—H8	0.93 (3)
C4—C7	1.516 (4)	C12—H12	0.9300
C5—C6	1.371 (4)	C14—H14	0.9300
C10—C11	1.428 (3)	C15—H15	0.9300
C10—C13	1.489 (3)	C17—H17	0.9300
C11—C12	1.364 (3)	C18—H18	0.9300
C11—C20	1.487 (3)	C19—H19A	0.9600
C13—C14	1.384 (3)	C19—H19B	0.9600
C13—C18	1.388 (4)	C19—H19C	0.9600
C14—C15	1.384 (3)	C22—H22	0.9300
C15—C16	1.380 (4)	C23—H23	0.9300
C16—C17	1.381 (4)	C25—H25	0.9300
C16—C19	1.513 (3)	C26—H26	0.9300
C17—C18	1.381 (3)	C27—H27A	0.9600
C20—C21	1.488 (3)	C27—H27B	0.9600
C21—C22	1.392 (3)	C27—H27C	0.9600
O1···N1	2.708 (3)	C25···H19B^vi	3.1000
O1···C8	3.095 (3)	C25···H3^iv	2.9000
O2···C9^i	2.931 (3)	C26···H12	2.5700
O2···N2^i	3.021 (3)	C26···H3^iv	3.0600
O2···C8^i	3.273 (3)	H2···N1	2.5500
O2···C13	3.010 (2)	H3···H7B	2.4400
O2···C18	2.949 (2)	H3···C25^v	2.9000
O2···C12^i	3.414 (3)	H3···C26^v	3.0600
O1···H5^ii	2.8400	H5···H7A	2.4700
O1···H22^i	2.9000	H5···O1^vii	2.8400
O1···H27C^iii	2.9000	H5···H27A^viii	2.5600
O1···H27B^iv	2.7800	H6···H8	2.4000
O2···H18	2.7100	H7A···H5	2.4700
O2···H22	2.5900	H7A···H8^vii	2.5800
O2···H8^i	2.45 (2)	H7B···H3	2.4400
N1···O1	2.708 (3)	H8···C9	3.00 (3)
N1···C17^v	3.434 (4)	H8···H6	2.4000
N2···O2^i	3.021 (3)	H8···H7A^ii	2.5800
N1···H2	2.5500	H8···O2^i	2.45 (2)
N1···H17^v	2.8400	H12···C21	2.5900
N2···H17^v	2.9000	H12···C26	2.5700
N3···H14	2.5600	H12···H26	2.4100
N3···H25^iv	2.6300	H14···N3	2.5600
C3···C25^v	3.458 (4)	H15···H19C	2.4000
C3···C26^v	3.551 (4)	H17···H19B	2.5200
C8···O1	3.095 (3)	H17···N1^iv	2.8400
C8···O2^i	3.273 (3)	H17···N2^iv	2.9000
C9···O2^i	2.931 (3)	H18···O2	2.7100
C12···O2^i	3.414 (3)	H18···C11	2.8600
C12···C26	3.067 (4)	H18···C20	2.7200
C12···C17^v	3.567 (3)	H19B···C25^ix	3.1000
C13···O2	3.010 (2)	H19B···H17	2.5200
C17···C12^iv	3.567 (3)	H19C···H15	2.4000
C17···N1^iv	3.434 (4)	H22···O2	2.5900
C18···C20	3.172 (3)	H22···O1^i	2.9000
C18···O2	2.949 (2)	H23···H27C	2.5900
C20···C18	3.172 (3)	H23···C1^x	3.0700
C25···C3^iv	3.458 (4)	H25···H27B	2.3700
C26···C12	3.067 (4)	H25···N3^v	2.6300
C26···C3^iv	3.551 (4)	H25···C14^v	3.0700
C1···H23^iii	3.0700	H26···C11	2.8000
C9···H8	3.00 (3)	H26···C12	2.7400
C11···H26	2.8000	H26···H12	2.4100
C11···H18	2.8600	H26···C15^v	3.0900
C12···H26	2.7400	H26···C16^v	3.0500
C14···H25^iv	3.0700	H27A···H5^viii	2.5600
C15···H26^iv	3.0900	H27B···H25	2.3700
C16···H26^iv	3.0500	H27B···O1^v	2.7800
C20···H18	2.7200	H27C···H23	2.5900
C21···H12	2.5900	H27C···O1^x	2.9000
N2—N1—C8	114.9 (2)	C21—C26—C25	120.74 (19)
N1—N2—C9	119.1 (2)	C1—C2—H2	120.00
N1—N2—C12	118.67 (19)	C3—C2—H2	120.00
C9—N2—C12	122.15 (18)	C2—C3—H3	119.00
C9—N3—C10	122.01 (19)	C4—C3—H3	119.00
C2—C1—C6	118.4 (2)	C4—C5—H5	119.00
C2—C1—C8	122.3 (2)	C6—C5—H5	119.00
C6—C1—C8	119.2 (2)	C1—C6—H6	120.00
C1—C2—C3	120.6 (3)	C5—C6—H6	120.00
C2—C3—C4	121.1 (2)	C4—C7—H7A	109.00
C3—C4—C5	118.2 (2)	C4—C7—H7B	109.00
C3—C4—C7	120.6 (3)	C4—C7—H7C	110.00
C5—C4—C7	121.2 (3)	H7A—C7—H7B	109.00
C4—C5—C6	121.4 (3)	H7A—C7—H7C	110.00
C1—C6—C5	120.4 (3)	H7B—C7—H7C	109.00
N1—C8—C1	120.5 (2)	N1—C8—H8	121.5 (17)
O1—C9—N2	119.6 (2)	C1—C8—H8	117.6 (18)
O1—C9—N3	124.6 (2)	N2—C12—H12	119.00
N2—C9—N3	115.8 (2)	C11—C12—H12	119.00
N3—C10—C11	122.34 (18)	C13—C14—H14	120.00
N3—C10—C13	114.06 (18)	C15—C14—H14	120.00
C11—C10—C13	123.5 (2)	C14—C15—H15	119.00
C10—C11—C12	115.5 (2)	C16—C15—H15	120.00
C10—C11—C20	125.42 (16)	C16—C17—H17	119.00
C12—C11—C20	118.56 (18)	C18—C17—H17	119.00
N2—C12—C11	121.9 (2)	C13—C18—H18	120.00
C10—C13—C14	119.3 (2)	C17—C18—H18	120.00
C10—C13—C18	122.2 (2)	C16—C19—H19A	109.00
C14—C13—C18	118.36 (18)	C16—C19—H19B	110.00
C13—C14—C15	120.6 (3)	C16—C19—H19C	109.00
C14—C15—C16	121.1 (2)	H19A—C19—H19B	110.00
C15—C16—C17	118.3 (2)	H19A—C19—H19C	109.00
C15—C16—C19	120.8 (3)	H19B—C19—H19C	109.00
C17—C16—C19	120.9 (3)	C21—C22—H22	120.00
C16—C17—C18	121.1 (3)	C23—C22—H22	120.00
C13—C18—C17	120.6 (2)	C22—C23—H23	119.00
O2—C20—C11	120.0 (2)	C24—C23—H23	119.00
O2—C20—C21	121.0 (2)	C24—C25—H25	119.00
C11—C20—C21	118.89 (16)	C26—C25—H25	119.00
C20—C21—C22	118.44 (18)	C21—C26—H26	120.00
C20—C21—C26	123.41 (18)	C25—C26—H26	120.00
C22—C21—C26	118.1 (2)	C24—C27—H27A	109.00
C21—C22—C23	120.2 (2)	C24—C27—H27B	109.00
C22—C23—C24	122.1 (2)	C24—C27—H27C	110.00
C23—C24—C25	117.6 (2)	H27A—C27—H27B	109.00
C23—C24—C27	121.3 (2)	H27A—C27—H27C	109.00
C25—C24—C27	121.1 (2)	H27B—C27—H27C	109.00
C24—C25—C26	121.2 (2)
C8—N1—N2—C9	84.4 (3)	C11—C10—C13—C18	−37.2 (3)
C8—N1—N2—C12	−99.3 (3)	C20—C11—C12—N2	−169.4 (2)
N2—N1—C8—C1	−176.5 (2)	C10—C11—C20—O2	−26.4 (3)
N1—N2—C9—N3	170.3 (2)	C12—C11—C20—O2	144.6 (2)
C12—N2—C9—N3	−5.9 (3)	C12—C11—C20—C21	−32.6 (3)
N1—N2—C9—O1	−8.7 (3)	C10—C11—C20—C21	156.4 (2)
N1—N2—C12—C11	−173.8 (2)	C10—C11—C12—N2	2.6 (3)
C9—N2—C12—C11	2.3 (4)	C10—C13—C14—C15	174.82 (18)
C12—N2—C9—O1	175.2 (2)	C18—C13—C14—C15	0.2 (3)
C10—N3—C9—O1	−176.7 (2)	C10—C13—C18—C17	−174.80 (18)
C10—N3—C9—N2	4.4 (3)	C14—C13—C18—C17	−0.3 (3)
C9—N3—C10—C13	−176.6 (2)	C13—C14—C15—C16	−0.3 (3)
C9—N3—C10—C11	0.4 (3)	C14—C15—C16—C17	0.6 (3)
C6—C1—C2—C3	−0.4 (4)	C14—C15—C16—C19	−178.1 (2)
C8—C1—C6—C5	−175.8 (3)	C15—C16—C17—C18	−0.7 (3)
C8—C1—C2—C3	176.0 (2)	C19—C16—C17—C18	177.9 (2)
C2—C1—C8—N1	1.0 (4)	C16—C17—C18—C13	0.6 (3)
C2—C1—C6—C5	0.7 (4)	O2—C20—C21—C22	−29.6 (3)
C6—C1—C8—N1	177.4 (3)	O2—C20—C21—C26	148.8 (2)
C1—C2—C3—C4	−0.3 (4)	C11—C20—C21—C22	147.6 (2)
C2—C3—C4—C7	−177.9 (3)	C11—C20—C21—C26	−34.1 (3)
C2—C3—C4—C5	0.7 (4)	C20—C21—C22—C23	−179.4 (2)
C7—C4—C5—C6	178.2 (3)	C26—C21—C22—C23	2.1 (4)
C3—C4—C5—C6	−0.3 (5)	C20—C21—C26—C25	−179.7 (2)
C4—C5—C6—C1	−0.3 (5)	C22—C21—C26—C25	−1.3 (4)
C13—C10—C11—C12	172.6 (2)	C21—C22—C23—C24	−1.4 (4)
C13—C10—C11—C20	−16.1 (3)	C22—C23—C24—C25	−0.2 (4)
N3—C10—C11—C20	167.3 (2)	C22—C23—C24—C27	179.0 (3)
N3—C10—C13—C18	139.8 (2)	C23—C24—C25—C26	1.0 (4)
C11—C10—C13—C14	148.4 (2)	C27—C24—C25—C26	−178.2 (3)
N3—C10—C13—C14	−34.7 (3)	C24—C25—C26—C21	−0.2 (4)
N3—C10—C11—C12	−4.0 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^i	0.93 (3)	2.45 (2)	3.273 (3)	148 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.