A triazine derivative with a triple-decker sandwich conformation

In dimethyl 3,3′-[6-methoxy-1,3,5-triazine-2,4-diyl)bis(oxy)]bis(4-benzyloxy-5-methoxybenzoate), C₃₆H₃₃N₃O₁₁, a new triazine derivative, the benz­yloxy groups adopt an inter­esting conformation in which they are positioned above and below the triazine ring `core' of the mol­ecule to form an intra­molecular triple-decker sandwich. The ester carbonyl O atoms of adjacent mol­ecules in the crystal structure participate in non-conventional (alk­yl)C—H...O hydrogen bonds [averaging 2.45 (1)Å] about an inversion centre to give a weakly hydrogen-bonded dimer.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.066
• wR factor = 0.224
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         600 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.16 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C36 H33 N3 O11

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

   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
   1 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dimethyl 6,6'-bis(benzyloxy)-5,5'-dimethoxy)-3,3'-(6-methoxy-1,3,5-triazine-2,4- diyldioxy)dibenzoate

Crystal data

C36H33N3O11	Z = 2
Mr = 683.65	F(000) = 716
Triclinic, P1	Dx = 1.339 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5540 (7) Å	Cell parameters from 5868 reflections
b = 11.1363 (8) Å	θ = 4.3–27.0°
c = 17.9894 (13) Å	µ = 0.1 mm^−1
α = 92.746 (6)°	T = 295 K
β = 94.278 (6)°	Rhomb, colourless
γ = 96.246 (6)°	0.6 × 0.4 × 0.25 mm
V = 1696.0 (2) Å^3

Data collection

Xcalibur 2 CCD (Oxford Diffraction) diffractometer	Rint = 0.024
ω–2θ scans	θmax = 27.1°, θmin = 4.3°
13313 measured reflections	h = −10→10
7354 independent reflections	k = −14→14
4422 reflections with I > 2σ(I)	l = −23→15

Refinement

Refinement on F^2	55 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.066	w = 1/[σ^2(Fo^2) + (0.1153P)^2 + 0.3795P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.224	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.29 e Å^−3
7354 reflections	Δρmin = −0.19 e Å^−3
456 parameters

Special details

Experimental. ¹H NMR (500 MHz, CDCl₃): δ_H 4.12 (3H, s, OMe); ¹³C NMR (125 MHz, CDCl₃) δ_C 172.5, 171.4, 56.9 (OMe). A solution of 2,4-dichloro-6-methoxy-1,3,5-triazine (72 mg, 0.40 mmol) and methyl 4-benzyloxy-3-hydroxy-5-methoxybenzoate (58 mg, 0.20 mmol) in THF (20 ml) was stirred under nitrogen. N-Methylmorpholine (24 mg, 0.24 mmol) was added and, after stirring for 4 h, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed successively with a saturated NaHCO₃ solution, water, 1 N HCl, water and brine and dried over MgSO₄. The crude product was purified by column chromatography on SiO₂ (hexane:ethyl acetate = 7:3) to afford compound (I) as a cream white solid (92 mg, 67%). Recrystallization by slow evaporation of a methanol solution of (I) gave the compound as colourless crystals (m.p. 371–373 K). Atom numbering consistent with the crystallographic labelling scheme of Fig. 1 applies to the following characterization data where necessary. ¹H NMR (500 MHz, CDCl₃): δ_H 7.51 (2H, d, J = 1.9 Hz, H4/H24), 7.43 (2H, d, J = 1.9 Hz, H2/H22), 7.23–7.25 (10H, m, Ar—H), 5.06 (4H, s, –CH₂–), 3.92 (6H, s, COOMe), 3.90 (6H, s, C9-OMe/C29-OMe), 3.77 (3H, s, C206-OMe). ¹³C NMR (125 MHz, CDCl₃) δ_C 173.6 (C17/C19), 173.0 (C18), 165.9 (C=O), 153.3 (C5/C25), 144.7 (C6/C26), 144.0 (C3/C23) 136.9 (C11/C31), 128.2 (m-C, phenyl), 127.8 (p-C, phenyl), 127.6 (o-C, phenyl), 125.2 (C1/C21), 116.8 (C2/C22), 111.2 (C4/C24), 74.8 (C10/C30), 56.2 (C9/C29), 55.4 (C20), 52.2 (C8/C28).

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.

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

	x	y	z	Uiso*/Ueq
O9	0.43187 (19)	0.97507 (17)	0.10922 (8)	0.0613 (5)
O7	0.50934 (19)	1.20567 (17)	0.07447 (8)	0.0600 (5)
O5	0.76372 (19)	1.36046 (19)	0.28891 (9)	0.0668 (5)
N3	0.5002 (2)	1.29663 (19)	0.29074 (10)	0.0530 (5)
N2	0.6378 (2)	1.28141 (19)	0.18123 (10)	0.0551 (5)
N1	0.3636 (2)	1.21419 (19)	0.17642 (10)	0.0547 (5)
C21	0.3821 (3)	1.1353 (2)	0.03427 (11)	0.0523 (6)
C26	0.3459 (3)	1.0163 (2)	0.05108 (11)	0.0521 (6)
C19	0.5005 (3)	1.2336 (2)	0.14758 (11)	0.0504 (5)
O6	0.2428 (2)	1.2356 (2)	0.28547 (10)	0.0757 (6)
O4	0.6346 (3)	1.56798 (19)	0.31551 (9)	0.0752 (6)
C17	0.6251 (3)	1.3115 (2)	0.25289 (12)	0.0516 (5)
C23	0.1970 (3)	1.1110 (3)	−0.07233 (12)	0.0571 (6)
O3	0.6314 (3)	1.66590 (18)	0.45795 (10)	0.0742 (5)
C25	0.2291 (3)	0.9430 (2)	0.00470 (12)	0.0542 (6)
C18	0.3720 (3)	1.2480 (2)	0.24842 (12)	0.0539 (6)
C3	0.8256 (3)	1.3919 (3)	0.49222 (13)	0.0593 (6)
O8	0.1982 (2)	0.82689 (19)	0.02396 (10)	0.0719 (5)
C2	0.8244 (3)	1.3444 (3)	0.41953 (13)	0.0601 (6)
H2	0.868	1.273	0.4093	0.072*
C1	0.7573 (3)	1.4052 (3)	0.36288 (13)	0.0579 (6)
C4	0.7611 (3)	1.4979 (2)	0.50708 (12)	0.0569 (6)
H4	0.7623	1.5284	0.5562	0.068*
C5	0.6944 (3)	1.5596 (2)	0.44974 (13)	0.0565 (6)
C22	0.3102 (3)	1.1846 (2)	−0.02664 (12)	0.0574 (6)
H22	0.337	1.265	−0.0368	0.069*
C6	0.6920 (3)	1.5113 (2)	0.37585 (12)	0.0574 (6)
O10	0.0382 (3)	1.0929 (2)	−0.18775 (12)	0.0909 (7)
C24	0.1578 (3)	0.9921 (3)	−0.05680 (13)	0.0596 (6)
H24	0.0823	0.9438	−0.0881	0.072*
C27	0.1194 (3)	1.1560 (3)	−0.14049 (15)	0.0690 (8)
O2	0.9539 (3)	1.2276 (2)	0.53254 (12)	0.0915 (7)
O1	0.9036 (3)	1.3654 (3)	0.61981 (11)	0.0972 (7)
O11	0.1497 (3)	1.2749 (2)	−0.14429 (12)	0.0912 (7)
C30	0.3501 (4)	0.9087 (3)	0.16347 (14)	0.0748 (8)
H30A	0.3448	0.8226	0.1508	0.09*
H30B	0.2431	0.93	0.1637	0.09*
C36	0.5928 (3)	0.9801 (3)	0.24941 (15)	0.0713 (8)
H36	0.6507	0.9922	0.2081	0.086*
C31	0.4354 (3)	0.9379 (3)	0.23940 (13)	0.0620 (6)
C9	0.6291 (4)	1.7177 (3)	0.53138 (15)	0.0866 (9)
H9A	0.5714	1.6615	0.5609	0.13*
H9B	0.5792	1.7908	0.5295	0.13*
H9C	0.7353	1.736	0.5534	0.13*
C11	0.3976 (5)	1.5615 (3)	0.23491 (17)	0.0830 (9)
C29	0.1003 (4)	0.7446 (3)	−0.02769 (17)	0.0784 (8)
H29A	−0.0023	0.7717	−0.0348	0.118*
H29B	0.0907	0.6655	−0.0084	0.118*
H29C	0.1466	0.7415	−0.0746	0.118*
C7	0.8969 (3)	1.3297 (3)	0.55562 (15)	0.0702 (8)
C10	0.4734 (4)	1.5952 (3)	0.31184 (16)	0.0850 (9)
H10A	0.4705	1.6808	0.3236	0.102*
H10B	0.4162	1.5502	0.3481	0.102*
C35	0.6653 (4)	1.0046 (3)	0.32016 (18)	0.0861 (9)
H35	0.7717	1.0342	0.3262	0.103*
C20	0.0956 (4)	1.1851 (5)	0.2452 (2)	0.1134 (15)
H20A	0.0697	1.2359	0.2055	0.17*
H20B	0.0131	1.1805	0.2787	0.17*
H20C	0.1063	1.1055	0.2248	0.17*
C32	0.3533 (4)	0.9201 (4)	0.30148 (16)	0.0911 (10)
H32	0.2468	0.8911	0.2958	0.109*
C14	0.2542 (8)	1.4961 (4)	0.0923 (3)	0.1370 (19)
H14	0.206	1.4743	0.0448	0.164*
C8	1.0329 (5)	1.1636 (4)	0.5890 (2)	0.1075 (13)
H8A	1.1308	1.2099	0.6069	0.161*
H8B	1.0534	1.0865	0.568	0.161*
H8C	0.9672	1.1517	0.6296	0.161*
C12	0.2436 (5)	1.5122 (4)	0.2244 (2)	0.1117 (13)
H12	0.1854	1.5003	0.2656	0.134*
C16	0.4774 (7)	1.5768 (5)	0.1725 (2)	0.143 (2)
H16	0.5825	1.6099	0.1775	0.172*
C28	0.0851 (5)	1.3247 (5)	−0.2123 (2)	0.1219 (15)
H28A	0.1289	1.2899	−0.2548	0.183*
H28B	0.1115	1.4109	−0.2095	0.183*
H28C	−0.0276	1.3059	−0.2171	0.183*
C13	0.1726 (7)	1.4797 (5)	0.1536 (3)	0.143 (2)
H13	0.0677	1.4463	0.1479	0.172*
C34	0.5832 (5)	0.9860 (4)	0.38163 (17)	0.0925 (10)
H34	0.6334	1.0012	0.4293	0.111*
C33	0.4278 (5)	0.9451 (4)	0.37229 (17)	0.1019 (12)
H33	0.3706	0.9337	0.4139	0.122*
C15	0.4049 (9)	1.5441 (5)	0.1013 (2)	0.159 (2)
H15	0.462	1.5558	0.0597	0.191*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O9	0.0537 (9)	0.0918 (13)	0.0415 (8)	0.0190 (9)	0.0062 (7)	0.0072 (8)
O7	0.0572 (10)	0.0863 (12)	0.0351 (8)	0.0023 (8)	0.0080 (7)	−0.0051 (7)
O5	0.0518 (10)	0.1025 (14)	0.0440 (9)	0.0056 (9)	0.0056 (7)	−0.0138 (9)
N3	0.0528 (11)	0.0686 (13)	0.0385 (9)	0.0139 (9)	0.0036 (8)	−0.0048 (8)
N2	0.0511 (11)	0.0744 (14)	0.0396 (9)	0.0062 (9)	0.0072 (8)	−0.0027 (9)
N1	0.0521 (11)	0.0715 (13)	0.0412 (10)	0.0136 (9)	0.0053 (8)	−0.0071 (9)
C21	0.0467 (12)	0.0743 (17)	0.0365 (10)	0.0113 (11)	0.0071 (9)	−0.0078 (10)
C26	0.0468 (12)	0.0782 (17)	0.0337 (10)	0.0184 (11)	0.0068 (8)	−0.0034 (10)
C19	0.0530 (13)	0.0634 (14)	0.0363 (10)	0.0148 (10)	0.0049 (9)	−0.0007 (9)
O6	0.0535 (10)	0.1190 (16)	0.0528 (10)	0.0075 (10)	0.0132 (8)	−0.0203 (10)
O4	0.0914 (14)	0.0913 (14)	0.0434 (9)	0.0097 (11)	0.0055 (9)	0.0108 (9)
C17	0.0486 (12)	0.0645 (15)	0.0422 (11)	0.0104 (10)	0.0039 (9)	−0.0021 (10)
C23	0.0499 (13)	0.0804 (18)	0.0433 (12)	0.0181 (12)	0.0055 (10)	−0.0009 (11)
O3	0.1020 (15)	0.0717 (12)	0.0478 (10)	0.0098 (11)	0.0045 (9)	−0.0041 (8)
C25	0.0524 (13)	0.0682 (16)	0.0434 (11)	0.0111 (11)	0.0104 (10)	−0.0027 (10)
C18	0.0523 (13)	0.0700 (16)	0.0412 (11)	0.0172 (11)	0.0064 (9)	−0.0043 (10)
C3	0.0478 (13)	0.0799 (18)	0.0467 (12)	−0.0044 (12)	−0.0026 (10)	0.0049 (11)
O8	0.0805 (13)	0.0774 (13)	0.0550 (10)	0.0033 (10)	−0.0013 (9)	−0.0021 (9)
C2	0.0483 (13)	0.0777 (17)	0.0524 (13)	0.0042 (11)	0.0008 (10)	−0.0032 (12)
C1	0.0476 (12)	0.0812 (18)	0.0424 (12)	−0.0001 (12)	0.0037 (9)	−0.0067 (11)
C4	0.0537 (13)	0.0733 (17)	0.0396 (11)	−0.0068 (12)	0.0011 (9)	−0.0025 (10)
C5	0.0591 (14)	0.0619 (15)	0.0453 (12)	−0.0049 (11)	0.0047 (10)	−0.0021 (10)
C22	0.0610 (14)	0.0718 (16)	0.0412 (11)	0.0174 (12)	0.0067 (10)	−0.0035 (11)
C6	0.0584 (14)	0.0738 (17)	0.0367 (11)	−0.0038 (12)	0.0000 (10)	0.0013 (10)
O10	0.0735 (13)	0.132 (2)	0.0648 (12)	0.0167 (12)	−0.0182 (10)	0.0031 (12)
C24	0.0486 (13)	0.0853 (19)	0.0442 (12)	0.0097 (12)	0.0038 (10)	−0.0084 (12)
C27	0.0535 (14)	0.103 (2)	0.0531 (14)	0.0220 (15)	0.0027 (12)	0.0042 (15)
O2	0.0896 (15)	0.1150 (19)	0.0738 (13)	0.0322 (13)	−0.0054 (11)	0.0175 (12)
O1	0.0969 (16)	0.145 (2)	0.0520 (11)	0.0264 (14)	−0.0045 (10)	0.0155 (12)
O11	0.0956 (16)	0.1089 (19)	0.0720 (13)	0.0271 (13)	−0.0077 (11)	0.0216 (12)
C30	0.0783 (19)	0.098 (2)	0.0466 (13)	0.0021 (16)	0.0043 (12)	0.0107 (13)
C36	0.0656 (17)	0.098 (2)	0.0543 (14)	0.0226 (15)	0.0036 (12)	0.0122 (14)
C31	0.0659 (16)	0.0771 (18)	0.0460 (12)	0.0190 (13)	0.0043 (11)	0.0091 (11)
C9	0.119 (3)	0.085 (2)	0.0542 (16)	0.0052 (18)	0.0163 (16)	−0.0124 (14)
C11	0.117 (3)	0.0700 (19)	0.0608 (16)	0.0226 (17)	−0.0187 (16)	0.0039 (14)
C29	0.0793 (19)	0.084 (2)	0.0671 (17)	−0.0049 (15)	0.0026 (14)	−0.0084 (15)
C7	0.0511 (14)	0.100 (2)	0.0583 (16)	0.0027 (14)	0.0004 (11)	0.0124 (15)
C10	0.101 (2)	0.103 (2)	0.0528 (15)	0.0336 (19)	−0.0105 (15)	−0.0004 (15)
C35	0.0730 (19)	0.112 (3)	0.0737 (19)	0.0181 (17)	−0.0129 (15)	0.0184 (18)
C20	0.0517 (17)	0.199 (5)	0.082 (2)	−0.004 (2)	0.0147 (15)	−0.042 (2)
C32	0.081 (2)	0.140 (3)	0.0530 (16)	0.009 (2)	0.0127 (14)	0.0110 (17)
C14	0.213 (5)	0.103 (3)	0.086 (3)	0.038 (3)	−0.066 (3)	−0.018 (2)
C8	0.091 (2)	0.138 (3)	0.102 (3)	0.038 (2)	0.003 (2)	0.044 (2)
C12	0.105 (3)	0.135 (4)	0.093 (2)	0.043 (2)	−0.021 (2)	−0.025 (2)
C16	0.199 (5)	0.159 (4)	0.0511 (18)	−0.062 (4)	−0.015 (2)	0.009 (2)
C28	0.123 (3)	0.154 (4)	0.096 (3)	0.048 (3)	−0.017 (2)	0.046 (3)
C13	0.131 (4)	0.165 (5)	0.127 (4)	0.055 (3)	−0.054 (3)	−0.056 (3)
C34	0.116 (3)	0.110 (3)	0.0515 (16)	0.028 (2)	−0.0146 (17)	0.0078 (16)
C33	0.111 (3)	0.150 (4)	0.0485 (16)	0.021 (3)	0.0149 (17)	0.0110 (18)
C15	0.259 (6)	0.139 (4)	0.057 (2)	−0.052 (4)	−0.025 (3)	0.012 (2)

Geometric parameters (Å, º)

O9—C26	1.361 (3)	C30—C31	1.504 (4)
O9—C30	1.431 (3)	C30—H30A	0.97
O7—C19	1.346 (2)	C30—H30B	0.97
O7—C21	1.401 (3)	C36—C31	1.373 (4)
O5—C17	1.354 (3)	C36—C35	1.375 (4)
O5—C1	1.405 (3)	C36—H36	0.93
N3—C17	1.309 (3)	C31—C32	1.374 (4)
N3—C18	1.335 (3)	C9—H9A	0.96
N2—C19	1.325 (3)	C9—H9B	0.96
N2—C17	1.331 (3)	C9—H9C	0.96
N1—C19	1.317 (3)	C11—C16	1.366 (6)
N1—C18	1.326 (3)	C11—C12	1.367 (6)
C21—C26	1.380 (4)	C11—C10	1.497 (4)
C21—C22	1.382 (3)	C29—H29A	0.96
C26—C25	1.412 (3)	C29—H29B	0.96
O6—C18	1.331 (3)	C29—H29C	0.96
O6—C20	1.448 (4)	C10—H10A	0.97
O4—C6	1.368 (3)	C10—H10B	0.97
O4—C10	1.441 (4)	C35—C34	1.366 (5)
C23—C24	1.377 (4)	C35—H35	0.93
C23—C22	1.389 (4)	C20—H20A	0.96
C23—C27	1.485 (4)	C20—H20B	0.96
O3—C5	1.359 (3)	C20—H20C	0.96
O3—C9	1.418 (3)	C32—C33	1.383 (4)
C25—O8	1.358 (3)	C32—H32	0.93
C25—C24	1.387 (3)	C14—C15	1.336 (8)
C3—C4	1.379 (4)	C14—C13	1.357 (8)
C3—C2	1.386 (3)	C14—H14	0.93
C3—C7	1.489 (4)	C8—H8A	0.96
O8—C29	1.428 (3)	C8—H8B	0.96
C2—C1	1.375 (4)	C8—H8C	0.96
C2—H2	0.93	C12—C13	1.383 (5)
C1—C6	1.379 (4)	C12—H12	0.93
C4—C5	1.389 (3)	C16—C15	1.394 (5)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.408 (3)	C28—H28A	0.96
C22—H22	0.93	C28—H28B	0.96
O10—C27	1.203 (3)	C28—H28C	0.96
C24—H24	0.93	C13—H13	0.93
C27—O11	1.328 (4)	C34—C33	1.352 (5)
O2—C7	1.344 (4)	C34—H34	0.93
O2—C8	1.438 (4)	C33—H33	0.93
O1—C7	1.198 (3)	C15—H15	0.93
O11—C28	1.463 (4)
C26—O9—C30	118.52 (19)	C32—C31—C30	118.8 (3)
C19—O7—C21	119.18 (17)	O3—C9—H9A	109.5
C17—O5—C1	116.27 (18)	O3—C9—H9B	109.5
C17—N3—C18	112.43 (18)	H9A—C9—H9B	109.5
C19—N2—C17	111.43 (19)	O3—C9—H9C	109.5
C19—N1—C18	112.6 (2)	H9A—C9—H9C	109.5
C26—C21—C22	122.6 (2)	H9B—C9—H9C	109.5
C26—C21—O7	119.3 (2)	C16—C11—C12	116.9 (3)
C22—C21—O7	117.7 (2)	C16—C11—C10	122.4 (4)
O9—C26—C21	117.5 (2)	C12—C11—C10	120.7 (3)
O9—C26—C25	123.9 (2)	O8—C29—H29A	109.5
C21—C26—C25	118.5 (2)	O8—C29—H29B	109.5
N1—C19—N2	128.26 (19)	H29A—C29—H29B	109.5
N1—C19—O7	119.2 (2)	O8—C29—H29C	109.5
N2—C19—O7	112.53 (19)	H29A—C29—H29C	109.5
C18—O6—C20	118.4 (2)	H29B—C29—H29C	109.5
C6—O4—C10	119.0 (2)	O1—C7—O2	123.4 (3)
N3—C17—N2	128.4 (2)	O1—C7—C3	124.6 (3)
N3—C17—O5	118.73 (19)	O2—C7—C3	112.0 (2)
N2—C17—O5	112.86 (19)	O4—C10—C11	109.2 (3)
C24—C23—C22	120.5 (2)	O4—C10—H10A	109.8
C24—C23—C27	118.1 (2)	C11—C10—H10A	109.8
C22—C23—C27	121.4 (3)	O4—C10—H10B	109.8
C5—O3—C9	117.8 (2)	C11—C10—H10B	109.8
O8—C25—C24	125.1 (2)	H10A—C10—H10B	108.3
O8—C25—C26	115.9 (2)	C34—C35—C36	120.8 (3)
C24—C25—C26	119.0 (2)	C34—C35—H35	119.6
N1—C18—O6	119.8 (2)	C36—C35—H35	119.6
N1—C18—N3	126.9 (2)	O6—C20—H20A	109.5
O6—C18—N3	113.28 (19)	O6—C20—H20B	109.5
C4—C3—C2	120.5 (2)	H20A—C20—H20B	109.5
C4—C3—C7	118.8 (2)	O6—C20—H20C	109.5
C2—C3—C7	120.6 (3)	H20A—C20—H20C	109.5
C25—O8—C29	117.7 (2)	H20B—C20—H20C	109.5
C1—C2—C3	118.5 (3)	C31—C32—C33	120.6 (3)
C1—C2—H2	120.8	C31—C32—H32	119.7
C3—C2—H2	120.8	C33—C32—H32	119.7
C2—C1—C6	122.4 (2)	C15—C14—C13	118.9 (4)
C2—C1—O5	118.4 (2)	C15—C14—H14	120.5
C6—C1—O5	119.1 (2)	C13—C14—H14	120.5
C3—C4—C5	120.9 (2)	O2—C8—H8A	109.5
C3—C4—H4	119.5	O2—C8—H8B	109.5
C5—C4—H4	119.5	H8A—C8—H8B	109.5
O3—C5—C4	125.7 (2)	O2—C8—H8C	109.5
O3—C5—C6	115.6 (2)	H8A—C8—H8C	109.5
C4—C5—C6	118.7 (2)	H8B—C8—H8C	109.5
C21—C22—C23	118.3 (3)	C11—C12—C13	121.3 (5)
C21—C22—H22	120.8	C11—C12—H12	119.3
C23—C22—H22	120.8	C13—C12—H12	119.3
O4—C6—C1	118.0 (2)	C11—C16—C15	121.5 (5)
O4—C6—C5	122.9 (2)	C11—C16—H16	119.3
C1—C6—C5	118.9 (2)	C15—C16—H16	119.3
C23—C24—C25	121.2 (2)	O11—C28—H28A	109.5
C23—C24—H24	119.4	O11—C28—H28B	109.5
C25—C24—H24	119.4	H28A—C28—H28B	109.5
O10—C27—O11	122.9 (3)	O11—C28—H28C	109.5
O10—C27—C23	124.5 (3)	H28A—C28—H28C	109.5
O11—C27—C23	112.6 (2)	H28B—C28—H28C	109.5
C7—O2—C8	116.6 (3)	C14—C13—C12	120.8 (5)
C27—O11—C28	115.6 (3)	C14—C13—H13	119.6
O9—C30—C31	109.5 (2)	C12—C13—H13	119.6
O9—C30—H30A	109.8	C33—C34—C35	119.2 (3)
C31—C30—H30A	109.8	C33—C34—H34	120.4
O9—C30—H30B	109.8	C35—C34—H34	120.4
C31—C30—H30B	109.8	C34—C33—C32	120.6 (3)
H30A—C30—H30B	108.2	C34—C33—H33	119.7
C31—C36—C35	120.4 (3)	C32—C33—H33	119.7
C31—C36—H36	119.8	C14—C15—C16	120.6 (5)
C35—C36—H36	119.8	C14—C15—H15	119.7
C36—C31—C32	118.5 (3)	C16—C15—H15	119.7
C36—C31—C30	122.7 (2)
C19—O7—C21—C26	−66.6 (3)	C10—O4—C6—C1	124.9 (3)
C19—O7—C21—C22	121.0 (2)	C10—O4—C6—C5	−58.4 (3)
C30—O9—C26—C21	132.6 (2)	C2—C1—C6—O4	177.0 (2)
C30—O9—C26—C25	−51.3 (3)	O5—C1—C6—O4	0.6 (3)
C22—C21—C26—O9	175.42 (19)	C2—C1—C6—C5	0.2 (4)
O7—C21—C26—O9	3.3 (3)	O5—C1—C6—C5	−176.2 (2)
C22—C21—C26—C25	−0.9 (3)	O3—C5—C6—O4	1.8 (4)
O7—C21—C26—C25	−172.99 (18)	C4—C5—C6—O4	−177.3 (2)
C18—N1—C19—N2	−0.4 (4)	O3—C5—C6—C1	178.4 (2)
C18—N1—C19—O7	−178.8 (2)	C4—C5—C6—C1	−0.7 (4)
C17—N2—C19—N1	−0.3 (4)	C22—C23—C24—C25	0.4 (3)
C17—N2—C19—O7	178.2 (2)	C27—C23—C24—C25	178.1 (2)
C21—O7—C19—N1	−12.5 (3)	O8—C25—C24—C23	−179.7 (2)
C21—O7—C19—N2	168.8 (2)	C26—C25—C24—C23	−1.2 (3)
C18—N3—C17—N2	−2.1 (4)	C24—C23—C27—O10	−8.8 (4)
C18—N3—C17—O5	179.8 (2)	C22—C23—C27—O10	168.8 (3)
C19—N2—C17—N3	1.7 (4)	C24—C23—C27—O11	171.4 (2)
C19—N2—C17—O5	179.9 (2)	C22—C23—C27—O11	−10.9 (3)
C1—O5—C17—N3	−7.5 (3)	O10—C27—O11—C28	−3.4 (4)
C1—O5—C17—N2	174.1 (2)	C23—C27—O11—C28	176.4 (3)
O9—C26—C25—O8	4.0 (3)	C26—O9—C30—C31	−144.7 (2)
C21—C26—C25—O8	−179.92 (19)	C35—C36—C31—C32	−0.4 (5)
O9—C26—C25—C24	−174.65 (19)	C35—C36—C31—C30	−179.6 (3)
C21—C26—C25—C24	1.4 (3)	O9—C30—C31—C36	−23.6 (4)
C19—N1—C18—O6	179.2 (2)	O9—C30—C31—C32	157.3 (3)
C19—N1—C18—N3	−0.2 (4)	C8—O2—C7—O1	−3.1 (5)
C20—O6—C18—N1	−0.1 (4)	C8—O2—C7—C3	176.9 (3)
C20—O6—C18—N3	179.3 (3)	C4—C3—C7—O1	−0.4 (4)
C17—N3—C18—N1	1.3 (4)	C2—C3—C7—O1	179.4 (3)
C17—N3—C18—O6	−178.1 (2)	C4—C3—C7—O2	179.6 (2)
C24—C25—O8—C29	8.4 (4)	C2—C3—C7—O2	−0.5 (3)
C26—C25—O8—C29	−170.1 (2)	C6—O4—C10—C11	−135.2 (3)
C4—C3—C2—C1	−0.1 (4)	C16—C11—C10—O4	−36.9 (5)
C7—C3—C2—C1	−179.9 (2)	C12—C11—C10—O4	142.4 (3)
C3—C2—C1—C6	0.2 (4)	C31—C36—C35—C34	0.9 (5)
C3—C2—C1—O5	176.6 (2)	C36—C31—C32—C33	0.4 (5)
C17—O5—C1—C2	110.3 (3)	C30—C31—C32—C33	179.6 (3)
C17—O5—C1—C6	−73.2 (3)	C16—C11—C12—C13	−0.1 (6)
C2—C3—C4—C5	−0.3 (4)	C10—C11—C12—C13	−179.4 (4)
C7—C3—C4—C5	179.5 (2)	C12—C11—C16—C15	0.2 (7)
C9—O3—C5—C4	−1.8 (4)	C10—C11—C16—C15	179.6 (5)
C9—O3—C5—C6	179.2 (2)	C15—C14—C13—C12	0.1 (8)
C3—C4—C5—O3	−178.3 (2)	C11—C12—C13—C14	−0.1 (7)
C3—C4—C5—C6	0.7 (4)	C36—C35—C34—C33	−1.3 (6)
C26—C21—C22—C23	0.1 (3)	C35—C34—C33—C32	1.2 (6)
O7—C21—C22—C23	172.3 (2)	C31—C32—C33—C34	−0.8 (6)
C24—C23—C22—C21	0.2 (3)	C13—C14—C15—C16	0.0 (9)
C27—C23—C22—C21	−177.4 (2)	C11—C16—C15—C14	−0.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···O10^i	0.96	2.45	3.272 (6)	144
C30—H30B···O10^i	0.97	2.46	3.381 (4)	157

Symmetry code: (i) −x, −y+2, −z.