2-(4-Methyl­benzoyl­oxymeth­yl)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetra­hydro­pyrimidin-1-yl)tetra­hydro­furan-3-yl 4-methyl­benzoate

The title compound, C₂₆H₂₆N₂O₇, is a thia­midine derivative. Geometric parameters are in the usual ranges. The crystal packing is stabilized by a classical N—H...O hydrogen bond, several weak C—H...O hydrogen bonds and a π–π stacking inter­action.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.109
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.90
           From the CIF: _reflns_number_total               2915
           Count of symmetry unique reflns         2957
           Completeness (_total/calc)             98.58%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

2-(4-Methylbenzoyloxymethyl)-5-(5-methyl-2,4-dioxo-1,2,3,4- tetrahydropyrimidin-1-yl)tetrahydrofuran-3-yl 4-methylbenzoate

Crystal data

C26H26N2O7	F(000) = 1008
Mr = 478.49	Dx = 1.343 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12526 reflections
a = 6.4353 (4) Å	θ = 2.1–27.2°
b = 10.6994 (7) Å	µ = 0.10 mm^−1
c = 34.373 (2) Å	T = 173 K
V = 2366.7 (3) Å^3	Plate, colourless
Z = 4	0.41 × 0.37 × 0.21 mm

Data collection

Stoe IPDS II two-circle diffractometer	2617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 26.9°, θmin = 2.0°
ω scans	h = −7→8
14101 measured reflections	k = −12→13
2915 independent reflections	l = −30→43

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0849P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2915 reflections	Δρmax = 0.21 e Å^−3
324 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (4)

Special details

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

	x	y	z	Uiso*/Ueq
O1	0.2866 (2)	0.72570 (12)	0.42924 (5)	0.0379 (4)
C2	0.4437 (3)	0.79795 (17)	0.44813 (6)	0.0338 (4)
H2	0.4020	0.8141	0.4757	0.041*
C3	0.6392 (3)	0.71751 (19)	0.44741 (6)	0.0365 (5)
H3A	0.7177	0.7296	0.4229	0.044*
H3B	0.7309	0.7369	0.4697	0.044*
C4	0.5538 (3)	0.58601 (18)	0.45023 (6)	0.0334 (4)
H4	0.6463	0.5246	0.4368	0.040*
C5	0.3394 (3)	0.59396 (17)	0.43041 (6)	0.0337 (4)
H5	0.2353	0.5494	0.4470	0.040*
C6	0.3315 (4)	0.54036 (19)	0.39000 (7)	0.0405 (5)
H6A	0.3539	0.4489	0.3908	0.049*
H6B	0.1941	0.5567	0.3781	0.049*
N11	0.4631 (3)	0.91655 (13)	0.42741 (5)	0.0324 (4)
C12	0.4756 (3)	1.02564 (16)	0.44913 (6)	0.0318 (4)
O12	0.4816 (3)	1.02562 (12)	0.48461 (4)	0.0375 (3)
N13	0.4792 (3)	1.13292 (14)	0.42732 (5)	0.0324 (4)
H13	0.485 (5)	1.203 (3)	0.4407 (9)	0.059 (8)*
C14	0.4795 (3)	1.14334 (17)	0.38715 (6)	0.0323 (4)
O14	0.4801 (3)	1.24594 (12)	0.37144 (4)	0.0385 (3)
C15	0.4799 (3)	1.02411 (17)	0.36630 (6)	0.0330 (4)
C16	0.4717 (3)	0.91799 (16)	0.38728 (6)	0.0330 (4)
H16	0.4718	0.8404	0.3738	0.040*
C17	0.4894 (4)	1.02642 (19)	0.32287 (6)	0.0441 (5)
H17A	0.4920	0.9406	0.3129	0.066*
H17B	0.6155	1.0703	0.3145	0.066*
H17C	0.3670	1.0699	0.3126	0.066*
O41	0.5281 (3)	0.55505 (11)	0.49105 (4)	0.0338 (3)
C41	0.4922 (4)	0.43202 (15)	0.49730 (6)	0.0323 (4)
O42	0.4735 (3)	0.35950 (12)	0.47044 (4)	0.0418 (4)
C42	0.4825 (3)	0.39654 (16)	0.53873 (6)	0.0316 (4)
C43	0.4731 (3)	0.26856 (18)	0.54713 (6)	0.0350 (4)
H43	0.4696	0.2089	0.5267	0.042*
C44	0.4689 (4)	0.22979 (19)	0.58560 (7)	0.0391 (5)
H44	0.4621	0.1430	0.5912	0.047*
C45	0.4743 (4)	0.3149 (2)	0.61605 (6)	0.0411 (5)
C46	0.4801 (4)	0.4426 (2)	0.60720 (6)	0.0396 (5)
H46	0.4803	0.5021	0.6277	0.048*
C47	0.4855 (3)	0.48373 (18)	0.56875 (6)	0.0341 (4)
H47	0.4913	0.5706	0.5631	0.041*
C48	0.4740 (4)	0.2689 (3)	0.65764 (7)	0.0534 (6)
H48A	0.4798	0.3405	0.6754	0.080*
H48B	0.5953	0.2153	0.6620	0.080*
H48C	0.3468	0.2210	0.6625	0.080*
O61	0.4941 (3)	0.60000 (13)	0.36749 (4)	0.0423 (4)
C61	0.4721 (4)	0.59410 (19)	0.32834 (7)	0.0439 (5)
O62	0.3329 (4)	0.53781 (18)	0.31272 (6)	0.0623 (5)
C62	0.6303 (4)	0.6715 (2)	0.30782 (7)	0.0420 (5)
C63	0.8134 (4)	0.7112 (2)	0.32561 (7)	0.0478 (6)
H63	0.8451	0.6850	0.3513	0.057*
C64	0.9498 (4)	0.7893 (2)	0.30558 (7)	0.0501 (6)
H64	1.0750	0.8151	0.3178	0.060*
C65	0.9068 (4)	0.8303 (2)	0.26801 (7)	0.0475 (6)
C66	0.7242 (5)	0.7886 (2)	0.25040 (7)	0.0488 (6)
H66	0.6920	0.8152	0.2247	0.059*
C67	0.5884 (5)	0.7088 (2)	0.26970 (7)	0.0464 (6)
H67	0.4668	0.6797	0.2569	0.056*
C68	1.0496 (5)	0.9194 (3)	0.24730 (8)	0.0595 (7)
H68A	1.0845	0.9890	0.2647	0.089*
H68B	0.9804	0.9518	0.2240	0.089*
H68C	1.1771	0.8755	0.2398	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (7)	0.0243 (6)	0.0522 (9)	−0.0014 (6)	−0.0065 (7)	0.0002 (6)
C2	0.0402 (11)	0.0256 (8)	0.0356 (10)	−0.0041 (8)	0.0007 (9)	0.0005 (7)
C3	0.0379 (11)	0.0339 (9)	0.0376 (11)	−0.0041 (9)	−0.0050 (9)	0.0040 (8)
C4	0.0388 (11)	0.0292 (8)	0.0321 (10)	0.0001 (8)	−0.0018 (8)	0.0025 (8)
C5	0.0399 (11)	0.0231 (8)	0.0381 (11)	−0.0025 (8)	−0.0034 (9)	0.0017 (7)
C6	0.0501 (13)	0.0304 (9)	0.0411 (11)	−0.0072 (9)	−0.0053 (9)	−0.0003 (8)
N11	0.0415 (9)	0.0229 (6)	0.0329 (8)	−0.0019 (7)	0.0032 (8)	−0.0024 (6)
C12	0.0325 (10)	0.0251 (7)	0.0380 (10)	−0.0012 (8)	0.0013 (8)	−0.0043 (7)
O12	0.0476 (9)	0.0320 (6)	0.0328 (7)	−0.0022 (7)	0.0015 (7)	−0.0041 (5)
N13	0.0379 (9)	0.0223 (6)	0.0371 (9)	−0.0006 (7)	0.0003 (8)	−0.0025 (6)
C14	0.0314 (9)	0.0278 (8)	0.0377 (10)	0.0013 (8)	0.0017 (8)	−0.0003 (7)
O14	0.0434 (8)	0.0275 (6)	0.0445 (8)	0.0013 (6)	0.0010 (7)	0.0052 (5)
C15	0.0374 (10)	0.0287 (8)	0.0329 (10)	0.0012 (9)	−0.0016 (8)	−0.0004 (7)
C16	0.0394 (10)	0.0266 (8)	0.0330 (9)	0.0006 (8)	0.0010 (9)	−0.0044 (7)
C17	0.0580 (14)	0.0386 (9)	0.0357 (11)	0.0014 (11)	−0.0013 (10)	0.0004 (8)
O41	0.0453 (8)	0.0237 (5)	0.0324 (7)	−0.0011 (6)	−0.0026 (6)	0.0022 (5)
C41	0.0370 (11)	0.0253 (8)	0.0345 (10)	0.0010 (8)	−0.0017 (8)	−0.0009 (7)
O42	0.0623 (10)	0.0272 (6)	0.0358 (7)	−0.0003 (7)	−0.0025 (8)	−0.0042 (6)
C42	0.0330 (10)	0.0279 (8)	0.0340 (10)	0.0008 (8)	−0.0019 (8)	−0.0002 (7)
C43	0.0361 (10)	0.0302 (8)	0.0388 (11)	0.0007 (9)	−0.0007 (9)	0.0024 (8)
C44	0.0381 (11)	0.0356 (9)	0.0436 (11)	0.0004 (9)	−0.0015 (9)	0.0093 (8)
C45	0.0318 (10)	0.0536 (12)	0.0379 (11)	0.0004 (10)	−0.0009 (9)	0.0071 (9)
C46	0.0338 (10)	0.0487 (11)	0.0365 (10)	0.0022 (10)	−0.0012 (9)	−0.0046 (9)
C47	0.0321 (10)	0.0337 (8)	0.0366 (10)	0.0003 (9)	−0.0017 (8)	−0.0042 (8)
C48	0.0473 (13)	0.0742 (16)	0.0386 (11)	0.0026 (14)	−0.0004 (11)	0.0130 (11)
O61	0.0536 (10)	0.0383 (7)	0.0349 (8)	−0.0047 (7)	−0.0041 (7)	−0.0013 (6)
C61	0.0577 (14)	0.0365 (9)	0.0376 (11)	0.0042 (11)	−0.0050 (11)	−0.0056 (9)
O62	0.0781 (14)	0.0653 (11)	0.0436 (9)	−0.0210 (11)	−0.0105 (9)	−0.0062 (9)
C62	0.0522 (13)	0.0385 (10)	0.0353 (11)	0.0063 (10)	0.0004 (10)	−0.0051 (9)
C63	0.0522 (14)	0.0525 (12)	0.0386 (11)	0.0097 (12)	−0.0018 (11)	−0.0013 (10)
C64	0.0494 (14)	0.0585 (13)	0.0423 (12)	0.0054 (12)	−0.0010 (11)	−0.0044 (11)
C65	0.0551 (14)	0.0471 (12)	0.0403 (12)	0.0058 (11)	0.0051 (11)	−0.0067 (10)
C66	0.0631 (16)	0.0478 (12)	0.0355 (11)	0.0062 (12)	0.0024 (11)	−0.0030 (10)
C67	0.0591 (15)	0.0458 (11)	0.0342 (11)	0.0031 (11)	−0.0044 (10)	−0.0084 (9)
C68	0.0648 (18)	0.0643 (15)	0.0492 (14)	−0.0074 (14)	0.0025 (13)	0.0017 (12)

Geometric parameters (Å, º)

O1—C2	1.429 (3)	C41—C42	1.475 (3)
O1—C5	1.450 (2)	C42—C47	1.391 (3)
C2—N11	1.460 (2)	C42—C43	1.401 (2)
C2—C3	1.525 (3)	C43—C44	1.386 (3)
C2—H2	1.0000	C43—H43	0.9500
C3—C4	1.514 (3)	C44—C45	1.388 (3)
C3—H3A	0.9900	C44—H44	0.9500
C3—H3B	0.9900	C45—C46	1.401 (3)
C4—O41	1.451 (2)	C45—C48	1.512 (3)
C4—C5	1.541 (3)	C46—C47	1.393 (3)
C4—H4	1.0000	C46—H46	0.9500
C5—C6	1.504 (3)	C47—H47	0.9500
C5—H5	1.0000	C48—H48A	0.9800
C6—O61	1.449 (3)	C48—H48B	0.9800
C6—H6A	0.9900	C48—H48C	0.9800
C6—H6B	0.9900	O61—C61	1.355 (3)
N11—C16	1.381 (3)	C61—O62	1.205 (3)
N11—C12	1.388 (2)	C61—C62	1.490 (4)
C12—O12	1.220 (2)	C62—C63	1.394 (4)
C12—N13	1.371 (2)	C62—C67	1.396 (3)
N13—C14	1.385 (3)	C63—C64	1.394 (4)
N13—H13	0.88 (3)	C63—H63	0.9500
C14—O14	1.224 (2)	C64—C65	1.392 (3)
C14—C15	1.463 (3)	C64—H64	0.9500
C15—C16	1.346 (3)	C65—C66	1.395 (4)
C15—C17	1.494 (3)	C65—C68	1.504 (4)
C16—H16	0.9500	C66—C67	1.390 (4)
C17—H17A	0.9800	C66—H66	0.9500
C17—H17B	0.9800	C67—H67	0.9500
C17—H17C	0.9800	C68—H68A	0.9800
O41—C41	1.354 (2)	C68—H68B	0.9800
C41—O42	1.212 (2)	C68—H68C	0.9800
C2—O1—C5	110.34 (15)	O42—C41—O41	121.25 (17)
O1—C2—N11	108.01 (17)	O42—C41—C42	124.50 (16)
O1—C2—C3	105.73 (15)	O41—C41—C42	114.24 (15)
N11—C2—C3	114.32 (17)	C47—C42—C43	120.21 (19)
O1—C2—H2	109.5	C47—C42—C41	122.88 (16)
N11—C2—H2	109.5	C43—C42—C41	116.90 (17)
C3—C2—H2	109.5	C44—C43—C42	119.35 (19)
C4—C3—C2	102.95 (17)	C44—C43—H43	120.3
C4—C3—H3A	111.2	C42—C43—H43	120.3
C2—C3—H3A	111.2	C43—C44—C45	121.53 (19)
C4—C3—H3B	111.2	C43—C44—H44	119.2
C2—C3—H3B	111.2	C45—C44—H44	119.2
H3A—C3—H3B	109.1	C44—C45—C46	118.5 (2)
O41—C4—C3	108.38 (16)	C44—C45—C48	120.0 (2)
O41—C4—C5	109.74 (17)	C46—C45—C48	121.5 (2)
C3—C4—C5	104.22 (16)	C47—C46—C45	121.0 (2)
O41—C4—H4	111.4	C47—C46—H46	119.5
C3—C4—H4	111.4	C45—C46—H46	119.5
C5—C4—H4	111.4	C42—C47—C46	119.44 (18)
O1—C5—C6	109.70 (17)	C42—C47—H47	120.3
O1—C5—C4	105.99 (15)	C46—C47—H47	120.3
C6—C5—C4	114.68 (18)	C45—C48—H48A	109.5
O1—C5—H5	108.8	C45—C48—H48B	109.5
C6—C5—H5	108.8	H48A—C48—H48B	109.5
C4—C5—H5	108.8	C45—C48—H48C	109.5
O61—C6—C5	107.51 (16)	H48A—C48—H48C	109.5
O61—C6—H6A	110.2	H48B—C48—H48C	109.5
C5—C6—H6A	110.2	C61—O61—C6	115.74 (18)
O61—C6—H6B	110.2	O62—C61—O61	122.9 (2)
C5—C6—H6B	110.2	O62—C61—C62	125.1 (2)
H6A—C6—H6B	108.5	O61—C61—C62	111.9 (2)
C16—N11—C12	121.71 (15)	C63—C62—C67	119.2 (2)
C16—N11—C2	120.02 (15)	C63—C62—C61	122.6 (2)
C12—N11—C2	118.26 (16)	C67—C62—C61	118.1 (2)
O12—C12—N13	123.10 (17)	C62—C63—C64	119.9 (2)
O12—C12—N11	122.63 (17)	C62—C63—H63	120.1
N13—C12—N11	114.26 (17)	C64—C63—H63	120.1
C12—N13—C14	127.76 (16)	C65—C64—C63	121.5 (3)
C12—N13—H13	115 (2)	C65—C64—H64	119.3
C14—N13—H13	117 (2)	C63—C64—H64	119.3
O14—C14—N13	120.81 (18)	C64—C65—C66	118.0 (2)
O14—C14—C15	124.47 (19)	C64—C65—C68	121.2 (3)
N13—C14—C15	114.72 (16)	C66—C65—C68	120.8 (2)
C16—C15—C14	118.21 (17)	C67—C66—C65	121.3 (2)
C16—C15—C17	123.43 (17)	C67—C66—H66	119.4
C14—C15—C17	118.36 (16)	C65—C66—H66	119.4
C15—C16—N11	123.12 (17)	C66—C67—C62	120.2 (3)
C15—C16—H16	118.4	C66—C67—H67	119.9
N11—C16—H16	118.4	C62—C67—H67	119.9
C15—C17—H17A	109.5	C65—C68—H68A	109.5
C15—C17—H17B	109.5	C65—C68—H68B	109.5
H17A—C17—H17B	109.5	H68A—C68—H68B	109.5
C15—C17—H17C	109.5	C65—C68—H68C	109.5
H17A—C17—H17C	109.5	H68A—C68—H68C	109.5
H17B—C17—H17C	109.5	H68B—C68—H68C	109.5
C41—O41—C4	113.26 (14)
C5—O1—C2—N11	144.99 (17)	C5—C4—O41—C41	79.2 (2)
C5—O1—C2—C3	22.2 (2)	C4—O41—C41—O42	−3.7 (3)
O1—C2—C3—C4	−32.4 (2)	C4—O41—C41—C42	175.27 (17)
N11—C2—C3—C4	−151.12 (17)	O42—C41—C42—C47	−173.9 (2)
C2—C3—C4—O41	−86.80 (19)	O41—C41—C42—C47	7.2 (3)
C2—C3—C4—C5	30.0 (2)	O42—C41—C42—C43	7.1 (3)
C2—O1—C5—C6	−127.14 (19)	O41—C41—C42—C43	−171.9 (2)
C2—O1—C5—C4	−2.8 (2)	C47—C42—C43—C44	−0.6 (3)
O41—C4—C5—O1	98.18 (17)	C41—C42—C43—C44	178.4 (2)
C3—C4—C5—O1	−17.7 (2)	C42—C43—C44—C45	−0.2 (3)
O41—C4—C5—C6	−140.64 (16)	C43—C44—C45—C46	1.2 (3)
C3—C4—C5—C6	103.48 (19)	C43—C44—C45—C48	−178.7 (2)
O1—C5—C6—O61	65.3 (2)	C44—C45—C46—C47	−1.6 (3)
C4—C5—C6—O61	−53.8 (2)	C48—C45—C46—C47	178.4 (2)
O1—C2—N11—C16	−45.8 (3)	C43—C42—C47—C46	0.3 (3)
C3—C2—N11—C16	71.6 (3)	C41—C42—C47—C46	−178.7 (2)
O1—C2—N11—C12	135.19 (19)	C45—C46—C47—C42	0.8 (3)
C3—C2—N11—C12	−107.4 (2)	C5—C6—O61—C61	−160.22 (18)
C16—N11—C12—O12	−175.2 (2)	C6—O61—C61—O62	−3.7 (3)
C2—N11—C12—O12	3.8 (3)	C6—O61—C61—C62	172.59 (18)
C16—N11—C12—N13	5.2 (3)	O62—C61—C62—C63	−165.0 (2)
C2—N11—C12—N13	−175.77 (19)	O61—C61—C62—C63	18.8 (3)
O12—C12—N13—C14	177.9 (2)	O62—C61—C62—C67	17.3 (4)
N11—C12—N13—C14	−2.6 (3)	O61—C61—C62—C67	−158.9 (2)
C12—N13—C14—O14	179.0 (2)	C67—C62—C63—C64	1.3 (3)
C12—N13—C14—C15	−1.3 (3)	C61—C62—C63—C64	−176.4 (2)
O14—C14—C15—C16	−177.7 (2)	C62—C63—C64—C65	0.7 (4)
N13—C14—C15—C16	2.6 (3)	C63—C64—C65—C66	−1.4 (4)
O14—C14—C15—C17	2.3 (3)	C63—C64—C65—C68	177.0 (2)
N13—C14—C15—C17	−177.4 (2)	C64—C65—C66—C67	0.2 (4)
C14—C15—C16—N11	−0.1 (3)	C68—C65—C66—C67	−178.3 (2)
C17—C15—C16—N11	179.9 (2)	C65—C66—C67—C62	1.7 (4)
C12—N11—C16—C15	−4.1 (3)	C63—C62—C67—C66	−2.5 (3)
C2—N11—C16—C15	176.8 (2)	C61—C62—C67—C66	175.3 (2)
C3—C4—O41—C41	−167.62 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O42^i	0.88 (3)	1.96 (3)	2.842 (2)	175 (3)
C2—H2···O12	1.00	2.34	2.751 (2)	104
C6—H6A···O14^ii	0.99	2.41	3.353 (2)	159
C16—H16···O61	0.95	2.59	3.473 (2)	156
C43—H43···O12^ii	0.95	2.44	3.373 (2)	168
C68—H68B···O62^iii	0.98	2.55	3.453 (4)	153

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