2,2',2''-[(2,4,6-Trimeth-oxy-benzene-1,3,5-tri-yl)tris-(methyl-ene)]tris-(isoindole-1,3-dione).

The title mol-ecule, C36H27N3O9, adopts an almost symmetric conformation in which the mean planes of the phthalimido units are inclined at dihedral angles of 81.1 (1), 85.3 (1) and 86.3 (1)° with respect to the plane of the central aromatic ring. The O atoms are involved in intra- and inter-molecular C-H⋯O hydrogen bonding. The crystal structure also features π-π arene inter-actions [minimum ring centroid separation = 3.683 (2) Å]. The present mode of non-covalent interactions leads to a three-dimensional supramolecular architecture.

Related literature

For hydrogen bonds in the solid state, see: Desiraju (2002 ▶); Desiraju & Steiner (1999 ▶); Steiner (2002 ▶). For C—H⋯O hydrogen bonds in ketones carrying a terminal pyridine subunit, see: Mazik et al. (2001 ▶). For a review on acyclic receptors based on a benzene-derived core, see: Mazik (2009 ▶).

Experimental

Crystal data

C36H27N3O9

M = 645.61

Triclinic,

a = 10.2370 (3) Å

b = 10.3671 (3) Å

c = 14.6501 (4) Å

α = 79.804 (1)°

β = 79.512 (1)°

γ = 83.874 (1)°

V = 1500.20 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.51 × 0.50 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.949, T max = 0.971

29692 measured reflections

8026 independent reflections

6992 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 0.96

8026 reflections

436 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008428/zq2198sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008428/zq2198Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008428/zq2198Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H27N3O9	Z = 2
Mr = 645.61	F(000) = 672
Triclinic, P1	Dx = 1.429 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2370 (3) Å	Cell parameters from 9907 reflections
b = 10.3671 (3) Å	θ = 2.3–29.2°
c = 14.6501 (4) Å	µ = 0.10 mm−1
α = 79.804 (1)°	T = 100 K
β = 79.512 (1)°	Irregular, colourless
γ = 83.874 (1)°	0.51 × 0.50 × 0.28 mm
V = 1500.20 (7) Å3

Bruker APEXII CCD area-detector diffractometer	8026 independent reflections
Radiation source: fine-focus sealed tube	6992 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
phi and ω scans	θmax = 29.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→13
Tmin = 0.949, Tmax = 0.971	k = −14→14
29692 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.958P] where P = (Fo2 + 2Fc2)/3
8026 reflections	(Δ/σ)max < 0.001
436 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.12796 (8)	0.66212 (7)	0.18783 (5)	0.01633 (15)
O2	0.22988 (8)	0.36078 (8)	0.45741 (5)	0.01958 (17)
O3	−0.12369 (9)	0.28557 (9)	0.30721 (6)	0.02355 (18)
O4	0.00470 (9)	0.69783 (9)	0.00364 (6)	0.02422 (18)
O5	−0.30723 (8)	0.65590 (9)	0.27100 (6)	0.02150 (17)
O6	0.48284 (9)	0.35909 (9)	0.24204 (6)	0.02684 (19)
O7	0.38511 (8)	0.80269 (8)	0.17348 (6)	0.02226 (17)
O8	0.15450 (10)	0.11530 (9)	0.61971 (6)	0.0286 (2)
O9	0.16627 (11)	0.05026 (11)	0.31774 (7)	0.0358 (2)
N1	−0.13167 (9)	0.64776 (9)	0.14771 (6)	0.01741 (18)
N2	0.40392 (9)	0.57826 (9)	0.22568 (7)	0.01757 (18)
N3	0.13324 (10)	0.10612 (10)	0.46635 (7)	0.0210 (2)
C1	0.00047 (10)	0.47455 (10)	0.24429 (7)	0.01530 (19)
C2	0.10435 (10)	0.54768 (10)	0.25067 (7)	0.01478 (19)
C3	0.18863 (10)	0.50669 (11)	0.31740 (7)	0.0156 (2)
C4	0.15679 (11)	0.39756 (11)	0.38509 (7)	0.0164 (2)
C5	0.05402 (11)	0.32162 (11)	0.38223 (8)	0.0177 (2)
C6	−0.02044 (11)	0.35899 (11)	0.30973 (8)	0.0172 (2)
C7	0.08112 (12)	0.77913 (11)	0.22889 (8)	0.0208 (2)
H7A	−0.0131	0.7745	0.2571	0.031*
H7B	0.0913	0.8568	0.1799	0.031*
H7C	0.1334	0.7854	0.2775	0.031*
C8	0.18680 (13)	0.43689 (14)	0.53196 (8)	0.0265 (3)
H8A	0.2009	0.5296	0.5079	0.040*
H8B	0.2382	0.4053	0.5829	0.040*
H8C	0.0919	0.4277	0.5560	0.040*
C9	−0.09626 (15)	0.20079 (13)	0.23660 (9)	0.0295 (3)
H9A	−0.0609	0.2516	0.1757	0.044*
H9B	−0.1787	0.1641	0.2319	0.044*
H9C	−0.0305	0.1291	0.2542	0.044*
C10	−0.08810 (11)	0.50962 (11)	0.16956 (8)	0.0177 (2)
H10A	−0.0395	0.4804	0.1110	0.021*
H10B	−0.1681	0.4592	0.1903	0.021*
C11	−0.08304 (11)	0.72973 (11)	0.06444 (8)	0.0187 (2)
C12	−0.16249 (11)	0.85805 (11)	0.06850 (8)	0.0191 (2)
C13	−0.15858 (13)	0.97272 (12)	0.00389 (9)	0.0247 (2)
H13	−0.0977	0.9794	−0.0537	0.030*
C14	−0.24767 (14)	1.07832 (13)	0.02669 (9)	0.0275 (3)
H14	−0.2475	1.1586	−0.0162	0.033*
C15	−0.33658 (13)	1.06813 (12)	0.11105 (10)	0.0270 (3)
H15	−0.3945	1.1423	0.1255	0.032*
C16	−0.34221 (12)	0.95084 (12)	0.17486 (9)	0.0225 (2)
H16	−0.4042	0.9428	0.2319	0.027*
C17	−0.25397 (11)	0.84723 (11)	0.15155 (8)	0.0181 (2)
C18	−0.23948 (11)	0.70940 (11)	0.20107 (7)	0.0172 (2)
C19	0.31307 (11)	0.57446 (12)	0.31515 (8)	0.0191 (2)
H19A	0.2872	0.6655	0.3271	0.023*
H19B	0.3601	0.5280	0.3663	0.023*
C20	0.48423 (11)	0.46919 (12)	0.19829 (8)	0.0194 (2)
C21	0.56744 (11)	0.51949 (12)	0.10683 (8)	0.0187 (2)
C22	0.66502 (12)	0.45525 (13)	0.04912 (9)	0.0234 (2)
H22	0.6892	0.3640	0.0648	0.028*
C23	0.72661 (12)	0.52973 (14)	−0.03315 (9)	0.0268 (3)
H23	0.7941	0.4883	−0.0743	0.032*
C24	0.69162 (12)	0.66280 (14)	−0.05616 (8)	0.0263 (3)
H24	0.7341	0.7105	−0.1134	0.032*
C25	0.59480 (12)	0.72803 (13)	0.00356 (8)	0.0218 (2)
H25	0.5716	0.8196	−0.0111	0.026*
C26	0.53433 (11)	0.65336 (11)	0.08482 (8)	0.0179 (2)
C27	0.43267 (11)	0.69367 (11)	0.16284 (8)	0.0176 (2)
C28	0.02137 (12)	0.20410 (12)	0.45709 (9)	0.0229 (2)
H28A	−0.0095	0.2347	0.5183	0.028*
H28B	−0.0529	0.1622	0.4421	0.028*
C29	0.19020 (12)	0.07027 (11)	0.54809 (8)	0.0200 (2)
C30	0.29838 (11)	−0.03345 (11)	0.52684 (8)	0.0189 (2)
C31	0.38234 (12)	−0.10727 (11)	0.58341 (8)	0.0210 (2)
H31	0.3772	−0.0964	0.6471	0.025*
C32	0.47546 (13)	−0.19880 (13)	0.54295 (10)	0.0269 (3)
H32	0.5346	−0.2516	0.5799	0.032*
C33	0.48304 (13)	−0.21396 (12)	0.44909 (10)	0.0279 (3)
H33	0.5482	−0.2755	0.4229	0.033*
C34	0.39607 (13)	−0.13983 (12)	0.39372 (9)	0.0258 (3)
H34	0.4000	−0.1503	0.3301	0.031*
C35	0.30401 (12)	−0.05075 (11)	0.43437 (8)	0.0204 (2)
C36	0.19708 (13)	0.03783 (12)	0.39463 (8)	0.0230 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0186 (4)	0.0158 (4)	0.0135 (3)	−0.0023 (3)	−0.0002 (3)	−0.0014 (3)
O2	0.0177 (4)	0.0257 (4)	0.0146 (3)	0.0032 (3)	−0.0047 (3)	−0.0021 (3)
O3	0.0212 (4)	0.0260 (4)	0.0239 (4)	−0.0106 (3)	−0.0042 (3)	0.0005 (3)
O4	0.0219 (4)	0.0305 (5)	0.0179 (4)	−0.0017 (3)	0.0002 (3)	−0.0014 (3)
O5	0.0215 (4)	0.0266 (4)	0.0153 (4)	−0.0039 (3)	−0.0015 (3)	−0.0006 (3)
O6	0.0302 (5)	0.0228 (4)	0.0264 (4)	−0.0015 (4)	−0.0057 (4)	−0.0001 (3)
O7	0.0208 (4)	0.0216 (4)	0.0243 (4)	−0.0010 (3)	−0.0020 (3)	−0.0056 (3)
O8	0.0334 (5)	0.0295 (5)	0.0180 (4)	0.0082 (4)	0.0013 (3)	−0.0033 (3)
O9	0.0465 (6)	0.0388 (6)	0.0265 (5)	−0.0001 (5)	−0.0157 (4)	−0.0095 (4)
N1	0.0163 (4)	0.0197 (4)	0.0152 (4)	−0.0014 (3)	−0.0030 (3)	0.0003 (3)
N2	0.0150 (4)	0.0211 (5)	0.0163 (4)	−0.0027 (3)	−0.0009 (3)	−0.0031 (3)
N3	0.0231 (5)	0.0189 (5)	0.0190 (4)	0.0004 (4)	−0.0030 (4)	0.0004 (4)
C1	0.0141 (5)	0.0177 (5)	0.0134 (4)	−0.0003 (4)	−0.0016 (4)	−0.0020 (4)
C2	0.0145 (5)	0.0166 (5)	0.0119 (4)	−0.0005 (4)	0.0007 (3)	−0.0021 (4)
C3	0.0139 (5)	0.0193 (5)	0.0136 (4)	−0.0013 (4)	−0.0007 (4)	−0.0039 (4)
C4	0.0144 (5)	0.0203 (5)	0.0133 (4)	0.0024 (4)	−0.0018 (4)	−0.0022 (4)
C5	0.0163 (5)	0.0181 (5)	0.0162 (5)	0.0002 (4)	−0.0004 (4)	0.0005 (4)
C6	0.0149 (5)	0.0191 (5)	0.0169 (5)	−0.0031 (4)	−0.0010 (4)	−0.0017 (4)
C7	0.0221 (5)	0.0191 (5)	0.0209 (5)	0.0011 (4)	−0.0021 (4)	−0.0052 (4)
C8	0.0266 (6)	0.0377 (7)	0.0148 (5)	0.0056 (5)	−0.0050 (4)	−0.0064 (5)
C9	0.0396 (7)	0.0272 (6)	0.0254 (6)	−0.0136 (5)	−0.0121 (5)	−0.0009 (5)
C10	0.0174 (5)	0.0190 (5)	0.0171 (5)	−0.0017 (4)	−0.0054 (4)	−0.0012 (4)
C11	0.0176 (5)	0.0227 (5)	0.0157 (5)	−0.0041 (4)	−0.0044 (4)	0.0001 (4)
C12	0.0182 (5)	0.0217 (5)	0.0179 (5)	−0.0037 (4)	−0.0053 (4)	−0.0006 (4)
C13	0.0252 (6)	0.0257 (6)	0.0217 (5)	−0.0053 (5)	−0.0051 (4)	0.0031 (4)
C14	0.0316 (7)	0.0212 (6)	0.0290 (6)	−0.0029 (5)	−0.0104 (5)	0.0043 (5)
C15	0.0269 (6)	0.0213 (6)	0.0340 (7)	0.0006 (5)	−0.0102 (5)	−0.0040 (5)
C16	0.0214 (5)	0.0237 (6)	0.0237 (5)	−0.0023 (4)	−0.0051 (4)	−0.0051 (4)
C17	0.0177 (5)	0.0200 (5)	0.0177 (5)	−0.0036 (4)	−0.0062 (4)	−0.0010 (4)
C18	0.0164 (5)	0.0210 (5)	0.0153 (5)	−0.0024 (4)	−0.0053 (4)	−0.0026 (4)
C19	0.0168 (5)	0.0267 (6)	0.0144 (5)	−0.0050 (4)	−0.0012 (4)	−0.0043 (4)
C20	0.0164 (5)	0.0237 (5)	0.0197 (5)	−0.0021 (4)	−0.0054 (4)	−0.0052 (4)
C21	0.0152 (5)	0.0245 (5)	0.0184 (5)	−0.0032 (4)	−0.0042 (4)	−0.0063 (4)
C22	0.0188 (5)	0.0291 (6)	0.0258 (6)	−0.0003 (4)	−0.0052 (4)	−0.0127 (5)
C23	0.0177 (5)	0.0432 (7)	0.0231 (6)	−0.0041 (5)	−0.0005 (4)	−0.0169 (5)
C24	0.0207 (6)	0.0422 (7)	0.0175 (5)	−0.0104 (5)	−0.0003 (4)	−0.0076 (5)
C25	0.0188 (5)	0.0289 (6)	0.0190 (5)	−0.0069 (4)	−0.0041 (4)	−0.0030 (4)
C26	0.0139 (5)	0.0244 (5)	0.0170 (5)	−0.0034 (4)	−0.0030 (4)	−0.0059 (4)
C27	0.0138 (5)	0.0229 (5)	0.0171 (5)	−0.0037 (4)	−0.0036 (4)	−0.0038 (4)
C28	0.0193 (5)	0.0224 (6)	0.0227 (5)	−0.0006 (4)	−0.0019 (4)	0.0057 (4)
C29	0.0208 (5)	0.0184 (5)	0.0178 (5)	−0.0009 (4)	0.0001 (4)	0.0010 (4)
C30	0.0187 (5)	0.0173 (5)	0.0193 (5)	−0.0026 (4)	0.0007 (4)	−0.0026 (4)
C31	0.0203 (5)	0.0207 (5)	0.0203 (5)	−0.0008 (4)	−0.0004 (4)	−0.0022 (4)
C32	0.0201 (6)	0.0252 (6)	0.0322 (6)	0.0021 (5)	−0.0015 (5)	−0.0016 (5)
C33	0.0246 (6)	0.0212 (6)	0.0364 (7)	−0.0008 (5)	0.0021 (5)	−0.0085 (5)
C34	0.0291 (6)	0.0236 (6)	0.0254 (6)	−0.0064 (5)	0.0026 (5)	−0.0104 (5)
C35	0.0220 (5)	0.0186 (5)	0.0209 (5)	−0.0051 (4)	−0.0012 (4)	−0.0041 (4)
C36	0.0270 (6)	0.0210 (5)	0.0219 (5)	−0.0054 (4)	−0.0042 (4)	−0.0034 (4)

O1—C2	1.3810 (13)	C11—C12	1.4881 (16)
O1—C7	1.4465 (13)	C12—C13	1.3816 (16)
O2—C4	1.3829 (13)	C12—C17	1.3889 (16)
O2—C8	1.4372 (14)	C13—C14	1.3955 (19)
O3—C6	1.3761 (13)	C13—H13	0.9500
O3—C9	1.4439 (16)	C14—C15	1.3899 (19)
O4—C11	1.2080 (14)	C14—H14	0.9500
O5—C18	1.2085 (14)	C15—C16	1.3960 (18)
O6—C20	1.2063 (15)	C15—H15	0.9500
O7—C27	1.2067 (14)	C16—C17	1.3772 (16)
O8—C29	1.2042 (14)	C16—H16	0.9500
O9—C36	1.2060 (15)	C17—C18	1.4889 (16)
N1—C18	1.3964 (14)	C19—H19A	0.9900
N1—C11	1.4000 (14)	C19—H19B	0.9900
N1—C10	1.4511 (14)	C20—C21	1.4915 (16)
N2—C27	1.3972 (14)	C21—C22	1.3806 (16)
N2—C20	1.3991 (15)	C21—C26	1.3878 (16)
N2—C19	1.4596 (14)	C22—C23	1.3944 (18)
N3—C36	1.3953 (15)	C22—H22	0.9500
N3—C29	1.4009 (15)	C23—C24	1.385 (2)
N3—C28	1.4564 (15)	C23—H23	0.9500
C1—C2	1.3956 (15)	C24—C25	1.3985 (17)
C1—C6	1.4048 (15)	C24—H24	0.9500
C1—C10	1.5176 (15)	C25—C26	1.3811 (16)
C2—C3	1.4008 (15)	C25—H25	0.9500
C3—C4	1.3905 (15)	C26—C27	1.4858 (15)
C3—C19	1.5116 (15)	C28—H28A	0.9900
C4—C5	1.3902 (16)	C28—H28B	0.9900
C5—C6	1.3947 (15)	C29—C30	1.4894 (16)
C5—C28	1.5098 (15)	C30—C31	1.3804 (16)
C7—H7A	0.9800	C30—C35	1.3877 (16)
C7—H7B	0.9800	C31—C32	1.4004 (17)
C7—H7C	0.9800	C31—H31	0.9500
C8—H8A	0.9800	C32—C33	1.3987 (19)
C8—H8B	0.9800	C32—H32	0.9500
C8—H8C	0.9800	C33—C34	1.392 (2)
C9—H9A	0.9800	C33—H33	0.9500
C9—H9B	0.9800	C34—C35	1.3786 (16)
C9—H9C	0.9800	C34—H34	0.9500
C10—H10A	0.9900	C35—C36	1.4862 (17)
C10—H10B	0.9900
C2—O1—C7	112.85 (8)	C17—C16—C15	117.15 (11)
C4—O2—C8	112.02 (9)	C17—C16—H16	121.4
C6—O3—C9	114.65 (9)	C15—C16—H16	121.4
C18—N1—C11	111.94 (9)	C16—C17—C12	121.89 (11)
C18—N1—C10	123.58 (9)	C16—C17—C18	130.24 (11)
C11—N1—C10	123.92 (9)	C12—C17—C18	107.80 (10)
C27—N2—C20	111.99 (9)	O5—C18—N1	124.86 (11)
C27—N2—C19	123.90 (9)	O5—C18—C17	129.13 (11)
C20—N2—C19	123.69 (10)	N1—C18—C17	105.96 (9)
C36—N3—C29	112.05 (10)	N2—C19—C3	112.88 (9)
C36—N3—C28	124.02 (10)	N2—C19—H19A	109.0
C29—N3—C28	123.93 (10)	C3—C19—H19A	109.0
O3—C6—C5	118.58 (10)	N2—C19—H19B	109.0
O3—C6—C1	119.46 (10)	C3—C19—H19B	109.0
C5—C6—C1	121.76 (10)	H19A—C19—H19B	107.8
C2—C1—C6	117.61 (10)	O6—C20—N2	125.21 (11)
C2—C1—C10	124.23 (9)	O6—C20—C21	129.24 (11)
C6—C1—C10	118.13 (9)	N2—C20—C21	105.56 (10)
O1—C2—C1	119.42 (9)	C22—C21—C26	121.27 (11)
O1—C2—C3	118.54 (9)	C22—C21—C20	130.47 (11)
C1—C2—C3	122.02 (10)	C26—C21—C20	108.25 (10)
C4—C3—C2	117.75 (10)	C21—C22—C23	117.28 (12)
C4—C3—C19	120.26 (10)	C21—C22—H22	121.4
C2—C3—C19	121.96 (10)	C23—C22—H22	121.4
O2—C4—C5	118.08 (10)	C24—C23—C22	121.47 (11)
O2—C4—C3	119.75 (10)	C24—C23—H23	119.3
C5—C4—C3	122.17 (10)	C22—C23—H23	119.3
C4—C5—C6	118.20 (10)	C23—C24—C25	121.02 (12)
C4—C5—C28	120.91 (10)	C23—C24—H24	119.5
C6—C5—C28	120.86 (10)	C25—C24—H24	119.5
O1—C7—H7A	109.5	C26—C25—C24	117.04 (12)
O1—C7—H7B	109.5	C26—C25—H25	121.5
H7A—C7—H7B	109.5	C24—C25—H25	121.5
O1—C7—H7C	109.5	C25—C26—C21	121.89 (11)
H7A—C7—H7C	109.5	C25—C26—C27	129.93 (11)
H7B—C7—H7C	109.5	C21—C26—C27	108.15 (10)
O2—C8—H8A	109.5	O7—C27—N2	125.44 (10)
O2—C8—H8B	109.5	O7—C27—C26	128.63 (11)
H8A—C8—H8B	109.5	N2—C27—C26	105.90 (9)
O2—C8—H8C	109.5	N3—C28—C5	113.73 (9)
H8A—C8—H8C	109.5	N3—C28—H28A	108.8
H8B—C8—H8C	109.5	C5—C28—H28A	108.8
O3—C9—H9A	109.5	N3—C28—H28B	108.8
O3—C9—H9B	109.5	C5—C28—H28B	108.8
H9A—C9—H9B	109.5	H28A—C28—H28B	107.7
O3—C9—H9C	109.5	O8—C29—N3	125.31 (11)
H9A—C9—H9C	109.5	O8—C29—C30	129.03 (11)
H9B—C9—H9C	109.5	N3—C29—C30	105.65 (9)
N1—C10—C1	115.94 (9)	C31—C30—C35	121.58 (11)
N1—C10—H10A	108.3	C31—C30—C29	130.32 (10)
C1—C10—H10A	108.3	C35—C30—C29	108.09 (10)
N1—C10—H10B	108.3	C30—C31—C32	117.13 (11)
C1—C10—H10B	108.3	C30—C31—H31	121.4
H10A—C10—H10B	107.4	C32—C31—H31	121.4
O4—C11—N1	125.15 (11)	C31—C32—C33	121.20 (12)
O4—C11—C12	129.32 (11)	C31—C32—H32	119.4
N1—C11—C12	105.53 (9)	C33—C32—H32	119.4
C13—C12—C17	121.30 (11)	C34—C33—C32	120.69 (12)
C13—C12—C11	130.13 (11)	C34—C33—H33	119.7
C17—C12—C11	108.52 (10)	C32—C33—H33	119.7
C12—C13—C14	117.29 (12)	C35—C34—C33	117.68 (12)
C12—C13—H13	121.4	C35—C34—H34	121.2
C14—C13—H13	121.4	C33—C34—H34	121.2
C15—C14—C13	121.17 (12)	C34—C35—C30	121.68 (12)
C15—C14—H14	119.4	C34—C35—C36	129.94 (11)
C13—C14—H14	119.4	C30—C35—C36	108.36 (10)
C16—C15—C14	121.15 (12)	O9—C36—N3	124.89 (12)
C16—C15—H15	119.4	O9—C36—C35	129.29 (12)
C14—C15—H15	119.4	N3—C36—C35	105.81 (10)
C9—O3—C6—C5	−104.74 (12)	C20—N2—C19—C3	−74.87 (13)
C9—O3—C6—C1	80.27 (13)	C4—C3—C19—N2	121.69 (11)
O3—C6—C1—C2	178.55 (9)	C2—C3—C19—N2	−56.16 (14)
C5—C6—C1—C2	3.73 (16)	C27—N2—C20—O6	177.12 (11)
O3—C6—C1—C10	−3.32 (15)	C19—N2—C20—O6	4.32 (18)
C5—C6—C1—C10	−178.14 (10)	C27—N2—C20—C21	−2.87 (12)
C7—O1—C2—C1	103.89 (11)	C19—N2—C20—C21	−175.67 (9)
C7—O1—C2—C3	−77.97 (12)	O6—C20—C21—C22	−1.0 (2)
C6—C1—C2—O1	−179.81 (9)	N2—C20—C21—C22	178.97 (11)
C10—C1—C2—O1	2.18 (15)	O6—C20—C21—C26	−179.56 (12)
C6—C1—C2—C3	2.11 (15)	N2—C20—C21—C26	0.44 (12)
C10—C1—C2—C3	−175.90 (10)	C26—C21—C22—C23	−1.46 (17)
O1—C2—C3—C4	174.67 (9)	C20—C21—C22—C23	−179.82 (11)
C1—C2—C3—C4	−7.24 (15)	C21—C22—C23—C24	0.08 (17)
O1—C2—C3—C19	−7.44 (15)	C22—C23—C24—C25	1.35 (18)
C1—C2—C3—C19	170.66 (10)	C23—C24—C25—C26	−1.35 (17)
C8—O2—C4—C5	−99.36 (12)	C24—C25—C26—C21	−0.03 (17)
C8—O2—C4—C3	81.54 (12)	C24—C25—C26—C27	177.75 (11)
C2—C3—C4—O2	−174.09 (9)	C22—C21—C26—C25	1.47 (17)
C19—C3—C4—O2	7.98 (15)	C20—C21—C26—C25	−179.84 (10)
C2—C3—C4—C5	6.85 (16)	C22—C21—C26—C27	−176.74 (10)
C19—C3—C4—C5	−171.08 (10)	C20—C21—C26—C27	1.95 (12)
O2—C4—C5—C6	179.58 (9)	C20—N2—C27—O7	−174.20 (11)
C3—C4—C5—C6	−1.34 (16)	C19—N2—C27—O7	−1.42 (17)
O2—C4—C5—C28	1.27 (15)	C20—N2—C27—C26	4.04 (12)
C3—C4—C5—C28	−179.66 (10)	C19—N2—C27—C26	176.82 (9)
O3—C6—C5—C4	−178.99 (10)	C25—C26—C27—O7	−3.5 (2)
C1—C6—C5—C4	−4.12 (16)	C21—C26—C27—O7	174.53 (11)
O3—C6—C5—C28	−0.68 (16)	C25—C26—C27—N2	178.36 (11)
C1—C6—C5—C28	174.19 (10)	C21—C26—C27—N2	−3.63 (12)
C18—N1—C10—C1	−81.93 (13)	C36—N3—C28—C5	−61.67 (15)
C11—N1—C10—C1	107.26 (12)	C29—N3—C28—C5	117.70 (12)
C2—C1—C10—N1	−42.09 (15)	C4—C5—C28—N3	−57.36 (15)
C6—C1—C10—N1	139.92 (10)	C6—C5—C28—N3	124.37 (12)
C18—N1—C11—O4	−175.72 (11)	C36—N3—C29—O8	179.36 (12)
C10—N1—C11—O4	−3.96 (18)	C28—N3—C29—O8	−0.08 (19)
C18—N1—C11—C12	3.69 (12)	C36—N3—C29—C30	−1.62 (13)
C10—N1—C11—C12	175.45 (9)	C28—N3—C29—C30	178.94 (10)
O4—C11—C12—C13	1.2 (2)	O8—C29—C30—C31	2.3 (2)
N1—C11—C12—C13	−178.18 (12)	N3—C29—C30—C31	−176.70 (12)
O4—C11—C12—C17	178.78 (12)	O8—C29—C30—C35	−178.89 (13)
N1—C11—C12—C17	−0.59 (12)	N3—C29—C30—C35	2.13 (12)
C17—C12—C13—C14	1.78 (18)	C35—C30—C31—C32	1.23 (17)
C11—C12—C13—C14	179.10 (12)	C29—C30—C31—C32	179.92 (12)
C12—C13—C14—C15	−0.01 (19)	C30—C31—C32—C33	0.27 (18)
C13—C14—C15—C16	−1.7 (2)	C31—C32—C33—C34	−1.2 (2)
C14—C15—C16—C17	1.49 (18)	C32—C33—C34—C35	0.67 (19)
C15—C16—C17—C12	0.28 (17)	C33—C34—C35—C30	0.82 (18)
C15—C16—C17—C18	−176.42 (11)	C33—C34—C35—C36	−177.85 (12)
C13—C12—C17—C16	−1.96 (18)	C31—C30—C35—C34	−1.83 (18)
C11—C12—C17—C16	−179.80 (10)	C29—C30—C35—C34	179.22 (11)
C13—C12—C17—C18	175.39 (10)	C31—C30—C35—C36	177.10 (11)
C11—C12—C17—C18	−2.45 (12)	C29—C30—C35—C36	−1.85 (13)
C11—N1—C18—O5	172.43 (10)	C29—N3—C36—O9	179.40 (12)
C10—N1—C18—O5	0.64 (17)	C28—N3—C36—O9	−1.2 (2)
C11—N1—C18—C17	−5.16 (12)	C29—N3—C36—C35	0.52 (13)
C10—N1—C18—C17	−176.95 (9)	C28—N3—C36—C35	179.97 (10)
C16—C17—C18—O5	4.2 (2)	C34—C35—C36—O9	0.9 (2)
C12—C17—C18—O5	−172.84 (11)	C30—C35—C36—O9	−177.93 (13)
C16—C17—C18—N1	−178.34 (11)	C34—C35—C36—N3	179.69 (12)
C12—C17—C18—N1	4.60 (12)	C30—C35—C36—N3	0.88 (13)
C27—N2—C19—C3	113.18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O8i	0.98	2.47	3.2068 (15)	132
C8—H8B···O5i	0.98	2.34	3.2920 (15)	165
C9—H9A···O4ii	0.98	2.56	3.4742 (15)	156
C9—H9C···O9	0.98	2.38	3.2684 (19)	151
C10—H10A···O4	0.99	2.54	2.9144 (14)	102
C10—H10B···O3	0.99	2.32	2.8017 (15)	109
C19—H19A···O7	0.99	2.54	2.9200 (15)	103
C19—H19B···O2	0.99	2.36	2.8457 (14)	109
C23—H23···O1iii	0.95	2.45	3.3231 (16)	153
C28—H28A···O8	0.99	2.52	2.9187 (16)	103
C28—H28B···O3	0.99	2.34	2.8289 (16)	109
C32—H32···O2iv	0.95	2.56	3.2917 (16)	134
C34—H34···O7v	0.95	2.46	3.4066 (15)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O8i	0.98	2.47	3.2068 (15)	132
C8—H8B⋯O5i	0.98	2.34	3.2920 (15)	165
C9—H9A⋯O4ii	0.98	2.56	3.4742 (15)	156
C9—H9C⋯O9	0.98	2.38	3.2684 (19)	151
C10—H10A⋯O4	0.99	2.54	2.9144 (14)	102
C10—H10B⋯O3	0.99	2.32	2.8017 (15)	109
C19—H19A⋯O7	0.99	2.54	2.9200 (15)	103
C19—H19B⋯O2	0.99	2.36	2.8457 (14)	109
C23—H23⋯O1iii	0.95	2.45	3.3231 (16)	153
C28—H28A⋯O8	0.99	2.52	2.9187 (16)	103
C28—H28B⋯O3	0.99	2.34	2.8289 (16)	109
C32—H32⋯O2iv	0.95	2.56	3.2917 (16)	134
C34—H34⋯O7v	0.95	2.46	3.4066 (15)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .