A four-armed Schiff base: 6,6',6'',6'''-tetra-meth-oxy-2,2',2'',2'''-[methanetetra-yltetra-kis(methylenenitrilo-methyl-idyne)]tetra-phenol.

In the structure of the title compound, C(37)H(40)N(4)O(8), penta-erythrityltetra-mine is bonded to four o-vanillin mol-ecules, forming a four-armed Schiff base mol-ecule. These mol-ecules are connected by inter-molecular C-H⋯O hydrogen bonds. Intramolecular C-H⋯N and O-H⋯N hydrogen bonds are also present.

Related literature

For related literature, see: Tanaka et al. (2006 ▶); Bernardo et al. (1996 ▶); Laliberte et al. (2004 ▶).

Experimental

Crystal data

C37H40N4O8

M = 668.73

Triclinic,

a = 11.3464 (11) Å

b = 12.4437 (12) Å

c = 13.0523 (14) Å

α = 75.861 (7)°

β = 88.893 (7)°

γ = 78.385 (7)°

V = 1749.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.18 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.984, T max = 0.987

16510 measured reflections

6221 independent reflections

3077 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.145

S = 0.94

6194 reflections

443 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT (Bruker, 2007 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020618/om2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020618/om2247Isup2.hkl

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

C37H40N4O8	Z = 2
Mr = 668.73	F000 = 708
Triclinic, P1	Dx = 1.269 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.3464 (11) Å	Cell parameters from 16510 reflections
b = 12.4437 (12) Å	θ = 1.0–25.1º
c = 13.0523 (14) Å	µ = 0.09 mm−1
α = 75.861 (7)º	T = 273 (2) K
β = 88.893 (7)º	Prism, yellow
γ = 78.385 (7)º	0.18 × 0.16 × 0.15 mm
V = 1749.6 (3) Å3

Bruker APEXII CCD area-detector diffractometer	6221 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.058
T = 273(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2007)	h = −13→13
Tmin = 0.984, Tmax = 0.987	k = −14→14
16510 measured reflections	l = −13→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.18 e Å−3
6194 reflections	Δρmin = −0.19 e Å−3
443 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (14)
Secondary atom site location: difference Fourier map

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
C1	−0.6783 (3)	0.6040 (3)	0.6346 (3)	0.1205 (14)
H1A	−0.7350	0.5856	0.5914	0.181*
H1B	−0.7208	0.6457	0.6816	0.181*
H1C	−0.6285	0.5355	0.6752	0.181*
C2	−0.5190 (3)	0.7057 (2)	0.6164 (2)	0.0661 (8)
C3	−0.4819 (3)	0.6681 (2)	0.7207 (2)	0.0689 (8)
H3	−0.5142	0.6112	0.7650	0.083*
C4	−0.3970 (3)	0.7138 (2)	0.7606 (2)	0.0705 (8)
H4A	−0.3729	0.6879	0.8315	0.085*
C5	−0.3483 (2)	0.7971 (2)	0.6962 (2)	0.0637 (7)
H5	−0.2922	0.8283	0.7239	0.076*
C6	−0.3823 (2)	0.8355 (2)	0.5891 (2)	0.0504 (6)
C7	−0.4681 (2)	0.7891 (2)	0.5489 (2)	0.0561 (7)
C8	−0.3299 (2)	0.9225 (2)	0.5203 (2)	0.0556 (7)
H8	−0.2759	0.9550	0.5492	0.067*
C9	−0.2957 (2)	1.0390 (2)	0.35387 (19)	0.0541 (7)
H9A	−0.2517	1.0717	0.3972	0.065*
H9B	−0.3559	1.0994	0.3116	0.065*
C10	−0.7806 (3)	1.3762 (3)	−0.1285 (3)	0.1135 (13)
H10A	−0.7593	1.4442	−0.1701	0.170*
H10B	−0.8450	1.3953	−0.0832	0.170*
H10C	−0.8063	1.3352	−0.1746	0.170*
C11	−0.6932 (2)	1.2070 (2)	−0.0018 (2)	0.0585 (7)
C12	−0.7994 (2)	1.1700 (3)	0.0167 (2)	0.0672 (8)
H12	−0.8709	1.2161	−0.0145	0.081*
C13	−0.8005 (3)	1.0645 (3)	0.0816 (3)	0.0773 (9)
H13	−0.8725	1.0393	0.0929	0.093*
C14	−0.6962 (2)	0.9971 (2)	0.1292 (2)	0.0680 (8)
H14	−0.6979	0.9259	0.1725	0.082*
C15	−0.5875 (2)	1.0334 (2)	0.11382 (19)	0.0511 (7)
C16	−0.5865 (2)	1.1396 (2)	0.0472 (2)	0.0527 (7)
C17	−0.4787 (2)	0.9634 (2)	0.16885 (19)	0.0567 (7)
H17	−0.4822	0.8927	0.2121	0.068*
C18	−0.2728 (2)	0.9217 (2)	0.21916 (19)	0.0540 (7)
H18A	−0.2174	0.8917	0.1707	0.065*
H18B	−0.2971	0.8584	0.2683	0.065*
C19	0.1639 (4)	1.4133 (3)	0.5082 (3)	0.1264 (14)
H19A	0.1696	1.3906	0.5840	0.190*
H19B	0.1277	1.4923	0.4858	0.190*
H19C	0.2429	1.4004	0.4803	0.190*
C20	0.0741 (2)	1.3692 (2)	0.3635 (2)	0.0667 (8)
C21	0.1075 (3)	1.4562 (2)	0.2895 (3)	0.0770 (9)
H21	0.1441	1.5075	0.3116	0.092*
C22	0.0876 (3)	1.4686 (2)	0.1828 (3)	0.0822 (9)
H22	0.1117	1.5272	0.1334	0.099*
C23	0.0320 (2)	1.3938 (2)	0.1502 (2)	0.0727 (8)
H23	0.0183	1.4023	0.0784	0.087*
C24	−0.0044 (2)	1.3052 (2)	0.2232 (2)	0.0509 (7)
C25	0.0163 (2)	1.2936 (2)	0.3301 (2)	0.0581 (7)
C26	−0.0634 (2)	1.2277 (2)	0.1863 (2)	0.0547 (7)
H26	−0.0732	1.2373	0.1138	0.066*
C27	−0.1624 (2)	1.0776 (2)	0.19919 (19)	0.0591 (7)
H27A	−0.1064	1.0425	0.1541	0.071*
H27B	−0.2297	1.1260	0.1550	0.071*
C28	0.3376 (3)	0.6069 (3)	−0.0230 (2)	0.0883 (10)
H28A	0.3091	0.6053	−0.0912	0.132*
H28B	0.3572	0.5312	0.0209	0.132*
H28C	0.4082	0.6394	−0.0308	0.132*
C29	0.2713 (2)	0.6854 (2)	0.1230 (2)	0.0519 (7)
C30	0.3835 (2)	0.6521 (2)	0.1727 (2)	0.0666 (8)
H30	0.4489	0.6186	0.1394	0.080*
C31	0.3984 (3)	0.6687 (3)	0.2720 (3)	0.0782 (9)
H31	0.4743	0.6462	0.3052	0.094*
C32	0.3036 (2)	0.7176 (2)	0.3220 (2)	0.0675 (8)
H32	0.3149	0.7272	0.3894	0.081*
C33	0.1896 (2)	0.7534 (2)	0.27244 (19)	0.0493 (6)
C34	0.1742 (2)	0.7371 (2)	0.1721 (2)	0.0472 (6)
C35	0.0911 (2)	0.8099 (2)	0.3253 (2)	0.0543 (7)
H35	0.1062	0.8195	0.3919	0.065*
C36	−0.1053 (2)	0.9013 (2)	0.3478 (2)	0.0583 (7)
H36A	−0.0667	0.9410	0.3885	0.070*
H36B	−0.1378	0.8435	0.3973	0.070*
C37	−0.2085 (2)	0.9849 (2)	0.28059 (18)	0.0475 (6)
N1	−0.37817 (18)	0.99528 (17)	0.16006 (15)	0.0527 (5)
N2	−0.10224 (18)	1.14746 (18)	0.24823 (16)	0.0586 (6)
N3	−0.01463 (19)	0.84665 (17)	0.28493 (15)	0.0544 (6)
N4	−0.35536 (17)	0.95591 (17)	0.42188 (17)	0.0542 (6)
O1	−0.68132 (17)	1.30936 (18)	−0.06743 (17)	0.0877 (6)
O2	−0.48359 (14)	1.17979 (14)	0.02791 (14)	0.0690 (5)
H2	−0.4272	1.1331	0.0611	0.104*
O3	−0.6060 (2)	0.6698 (2)	0.56997 (16)	0.1045 (8)
O4	−0.50509 (17)	0.82276 (16)	0.44657 (14)	0.0791 (6)
H4	−0.4688	0.8710	0.4150	0.119*
O5	0.24695 (16)	0.67307 (15)	0.02443 (14)	0.0692 (5)
O6	0.06588 (14)	0.77182 (15)	0.12026 (13)	0.0641 (5)
H6	0.0164	0.8014	0.1570	0.096*
O7	−0.01615 (18)	1.20882 (16)	0.40428 (14)	0.0870 (7)
H7	−0.0487	1.1704	0.3754	0.131*
O8	0.0914 (2)	1.34865 (17)	0.47009 (17)	0.1004 (7)

	U11	U22	U33	U12	U13	U23
C1	0.130 (3)	0.122 (3)	0.118 (3)	−0.077 (3)	0.002 (3)	−0.005 (3)
C2	0.080 (2)	0.0671 (19)	0.0570 (19)	−0.0297 (17)	0.0043 (16)	−0.0143 (16)
C3	0.091 (2)	0.0606 (19)	0.0545 (19)	−0.0213 (17)	0.0114 (17)	−0.0093 (16)
C4	0.087 (2)	0.071 (2)	0.0492 (17)	−0.0113 (17)	0.0006 (16)	−0.0090 (16)
C5	0.0650 (18)	0.076 (2)	0.0539 (18)	−0.0153 (16)	−0.0037 (14)	−0.0208 (16)
C6	0.0527 (15)	0.0560 (16)	0.0465 (16)	−0.0115 (13)	0.0051 (13)	−0.0200 (14)
C7	0.0656 (17)	0.0617 (18)	0.0441 (16)	−0.0180 (15)	0.0041 (14)	−0.0149 (14)
C8	0.0527 (16)	0.0623 (18)	0.0592 (18)	−0.0135 (14)	0.0050 (14)	−0.0273 (15)
C9	0.0607 (16)	0.0543 (16)	0.0512 (16)	−0.0170 (14)	0.0047 (14)	−0.0160 (14)
C10	0.117 (3)	0.082 (2)	0.121 (3)	−0.005 (2)	−0.033 (3)	0.005 (2)
C11	0.0613 (18)	0.0593 (19)	0.0583 (18)	−0.0161 (15)	−0.0014 (15)	−0.0173 (15)
C12	0.0532 (17)	0.076 (2)	0.075 (2)	−0.0103 (15)	−0.0054 (15)	−0.0256 (18)
C13	0.0562 (19)	0.088 (2)	0.097 (2)	−0.0291 (18)	0.0082 (18)	−0.030 (2)
C14	0.0591 (18)	0.0647 (19)	0.086 (2)	−0.0271 (16)	0.0036 (16)	−0.0172 (17)
C15	0.0527 (16)	0.0530 (16)	0.0543 (16)	−0.0208 (13)	0.0028 (13)	−0.0176 (14)
C16	0.0481 (16)	0.0660 (18)	0.0525 (16)	−0.0204 (14)	0.0039 (13)	−0.0236 (14)
C17	0.0643 (18)	0.0588 (17)	0.0540 (17)	−0.0225 (15)	0.0071 (14)	−0.0192 (14)
C18	0.0551 (16)	0.0551 (16)	0.0571 (16)	−0.0163 (14)	0.0036 (13)	−0.0197 (14)
C19	0.164 (4)	0.111 (3)	0.124 (3)	−0.049 (3)	−0.046 (3)	−0.046 (3)
C20	0.076 (2)	0.0602 (19)	0.067 (2)	−0.0202 (16)	−0.0088 (16)	−0.0167 (17)
C21	0.084 (2)	0.0555 (19)	0.097 (3)	−0.0239 (17)	−0.0023 (19)	−0.0208 (19)
C22	0.096 (2)	0.064 (2)	0.088 (3)	−0.0369 (18)	0.005 (2)	−0.0059 (19)
C23	0.084 (2)	0.070 (2)	0.0649 (19)	−0.0292 (17)	0.0038 (16)	−0.0058 (17)
C24	0.0545 (15)	0.0473 (16)	0.0500 (17)	−0.0126 (13)	0.0033 (13)	−0.0084 (13)
C25	0.0637 (17)	0.0510 (17)	0.0593 (18)	−0.0201 (14)	−0.0005 (14)	−0.0060 (15)
C26	0.0529 (16)	0.0597 (17)	0.0521 (16)	−0.0138 (14)	0.0036 (13)	−0.0132 (14)
C27	0.0687 (17)	0.0664 (17)	0.0486 (16)	−0.0295 (15)	−0.0004 (13)	−0.0130 (14)
C28	0.087 (2)	0.094 (2)	0.097 (2)	−0.0184 (19)	0.023 (2)	−0.050 (2)
C29	0.0546 (17)	0.0526 (16)	0.0486 (16)	−0.0155 (13)	0.0055 (14)	−0.0091 (13)
C30	0.0521 (18)	0.0663 (19)	0.076 (2)	−0.0059 (14)	0.0028 (16)	−0.0117 (17)
C31	0.0482 (18)	0.095 (2)	0.087 (2)	−0.0025 (16)	−0.0133 (17)	−0.021 (2)
C32	0.0580 (18)	0.084 (2)	0.0589 (18)	−0.0105 (16)	−0.0107 (15)	−0.0164 (16)
C33	0.0467 (15)	0.0541 (16)	0.0467 (15)	−0.0128 (13)	−0.0049 (13)	−0.0088 (13)
C34	0.0379 (14)	0.0488 (15)	0.0529 (16)	−0.0134 (12)	−0.0039 (13)	−0.0048 (13)
C35	0.0574 (17)	0.0608 (17)	0.0476 (16)	−0.0183 (14)	−0.0043 (14)	−0.0130 (14)
C36	0.0566 (16)	0.0681 (18)	0.0516 (16)	−0.0115 (14)	0.0032 (14)	−0.0183 (14)
C37	0.0524 (15)	0.0493 (15)	0.0433 (15)	−0.0156 (13)	0.0027 (13)	−0.0120 (13)
N1	0.0511 (13)	0.0596 (14)	0.0513 (13)	−0.0157 (11)	0.0025 (11)	−0.0175 (11)
N2	0.0651 (14)	0.0654 (15)	0.0520 (13)	−0.0311 (12)	0.0027 (11)	−0.0123 (12)
N3	0.0477 (13)	0.0636 (14)	0.0534 (13)	−0.0122 (11)	0.0016 (11)	−0.0162 (11)
N4	0.0533 (13)	0.0612 (14)	0.0519 (14)	−0.0156 (11)	0.0086 (11)	−0.0182 (12)
O1	0.0758 (14)	0.0767 (14)	0.0974 (16)	−0.0167 (12)	−0.0118 (12)	0.0055 (13)
O2	0.0564 (11)	0.0705 (12)	0.0794 (13)	−0.0261 (10)	0.0020 (10)	−0.0061 (10)
O3	0.1308 (19)	0.1312 (19)	0.0715 (14)	−0.0868 (17)	0.0009 (13)	−0.0134 (14)
O4	0.0976 (14)	0.0991 (15)	0.0501 (12)	−0.0504 (12)	−0.0052 (10)	−0.0104 (11)
O5	0.0691 (12)	0.0804 (14)	0.0596 (12)	−0.0096 (11)	0.0072 (10)	−0.0249 (11)
O6	0.0455 (10)	0.0858 (13)	0.0635 (11)	−0.0079 (9)	−0.0075 (9)	−0.0268 (10)
O7	0.1317 (18)	0.0847 (14)	0.0563 (12)	−0.0599 (14)	−0.0076 (12)	−0.0072 (11)
O8	0.149 (2)	0.0852 (15)	0.0793 (16)	−0.0509 (15)	−0.0278 (14)	−0.0184 (13)

C1—O3	1.401 (3)	C19—H19B	0.9600
C1—H1A	0.9600	C19—H19C	0.9600
C1—H1B	0.9600	C20—O8	1.362 (3)
C1—H1C	0.9600	C20—C21	1.375 (3)
C2—O3	1.369 (3)	C20—C25	1.402 (4)
C2—C3	1.371 (3)	C21—C22	1.381 (4)
C2—C7	1.400 (3)	C21—H21	0.9300
C3—C4	1.381 (4)	C22—C23	1.373 (4)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.369 (3)	C23—C24	1.396 (3)
C4—H4A	0.9300	C23—H23	0.9300
C5—C6	1.397 (3)	C24—C25	1.387 (3)
C5—H5	0.9300	C24—C26	1.453 (3)
C6—C7	1.397 (3)	C25—O7	1.353 (3)
C6—C8	1.447 (3)	C26—N2	1.270 (3)
C7—O4	1.346 (3)	C26—H26	0.9300
C8—N4	1.270 (3)	C27—N2	1.469 (3)
C8—H8	0.9300	C27—C37	1.535 (3)
C9—N4	1.457 (3)	C27—H27A	0.9700
C9—C37	1.535 (3)	C27—H27B	0.9700
C9—H9A	0.9700	C28—O5	1.415 (3)
C9—H9B	0.9700	C28—H28A	0.9600
C10—O1	1.390 (3)	C28—H28B	0.9600
C10—H10A	0.9600	C28—H28C	0.9600
C10—H10B	0.9600	C29—O5	1.372 (3)
C10—H10C	0.9600	C29—C30	1.378 (3)
C11—C12	1.371 (3)	C29—C34	1.389 (3)
C11—O1	1.380 (3)	C30—C31	1.381 (4)
C11—C16	1.392 (3)	C30—H30	0.9300
C12—C13	1.379 (4)	C31—C32	1.363 (4)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.365 (4)	C32—C33	1.397 (3)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.391 (3)	C33—C34	1.393 (3)
C14—H14	0.9300	C33—C35	1.452 (3)
C15—C16	1.396 (3)	C34—O6	1.353 (3)
C15—C17	1.447 (3)	C35—N3	1.270 (3)
C16—O2	1.356 (3)	C35—H35	0.9300
C17—N1	1.275 (3)	C36—N3	1.468 (3)
C17—H17	0.9300	C36—C37	1.525 (3)
C18—N1	1.454 (3)	C36—H36A	0.9700
C18—C37	1.534 (3)	C36—H36B	0.9700
C18—H18A	0.9700	O2—H2	0.8200
C18—H18B	0.9700	O4—H4	0.8200
C19—O8	1.432 (3)	O6—H6	0.8200
C19—H19A	0.9600	O7—H7	0.8200
O3—C1—H1A	109.5	C20—C21—C22	121.1 (3)
O3—C1—H1B	109.5	C20—C21—H21	119.5
H1A—C1—H1B	109.5	C22—C21—H21	119.5
O3—C1—H1C	109.5	C23—C22—C21	119.4 (3)
H1A—C1—H1C	109.5	C23—C22—H22	120.3
H1B—C1—H1C	109.5	C21—C22—H22	120.3
O3—C2—C3	125.3 (3)	C22—C23—C24	121.1 (3)
O3—C2—C7	114.8 (2)	C22—C23—H23	119.5
C3—C2—C7	119.8 (3)	C24—C23—H23	119.4
C2—C3—C4	120.6 (3)	C25—C24—C23	118.9 (2)
C2—C3—H3	119.7	C25—C24—C26	121.4 (2)
C4—C3—H3	119.7	C23—C24—C26	119.8 (2)
C5—C4—C3	120.3 (3)	O7—C25—C24	121.4 (2)
C5—C4—H4A	119.8	O7—C25—C20	118.3 (3)
C3—C4—H4A	119.8	C24—C25—C20	120.2 (3)
C4—C5—C6	120.4 (3)	N2—C26—C24	123.1 (2)
C4—C5—H5	119.8	N2—C26—H26	118.4
C6—C5—H5	119.8	C24—C26—H26	118.4
C7—C6—C5	119.1 (2)	N2—C27—C37	112.89 (19)
C7—C6—C8	120.2 (2)	N2—C27—H27A	109.0
C5—C6—C8	120.7 (2)	C37—C27—H27A	109.0
O4—C7—C6	122.0 (2)	N2—C27—H27B	109.0
O4—C7—C2	118.3 (2)	C37—C27—H27B	109.0
C6—C7—C2	119.6 (2)	H27A—C27—H27B	107.8
N4—C8—C6	122.1 (2)	O5—C28—H28A	109.5
N4—C8—H8	118.9	O5—C28—H28B	109.5
C6—C8—H8	118.9	H28A—C28—H28B	109.5
N4—C9—C37	111.28 (19)	O5—C28—H28C	109.5
N4—C9—H9A	109.4	H28A—C28—H28C	109.5
C37—C9—H9A	109.4	H28B—C28—H28C	109.5
N4—C9—H9B	109.4	O5—C29—C30	124.4 (3)
C37—C9—H9B	109.4	O5—C29—C34	115.6 (2)
H9A—C9—H9B	108.0	C30—C29—C34	120.0 (3)
O1—C10—H10A	109.5	C29—C30—C31	119.8 (3)
O1—C10—H10B	109.5	C29—C30—H30	120.1
H10A—C10—H10B	109.5	C31—C30—H30	120.1
O1—C10—H10C	109.5	C32—C31—C30	120.9 (3)
H10A—C10—H10C	109.5	C32—C31—H31	119.5
H10B—C10—H10C	109.5	C30—C31—H31	119.5
C12—C11—O1	125.0 (3)	C31—C32—C33	120.2 (3)
C12—C11—C16	120.1 (3)	C31—C32—H32	119.9
O1—C11—C16	114.9 (2)	C33—C32—H32	119.9
C11—C12—C13	120.2 (3)	C34—C33—C32	119.1 (3)
C11—C12—H12	119.9	C34—C33—C35	121.7 (2)
C13—C12—H12	119.9	C32—C33—C35	119.2 (2)
C14—C13—C12	120.3 (3)	O6—C34—C29	118.8 (2)
C14—C13—H13	119.9	O6—C34—C33	121.2 (2)
C12—C13—H13	119.9	C29—C34—C33	120.0 (2)
C13—C14—C15	120.8 (3)	N3—C35—C33	123.2 (2)
C13—C14—H14	119.6	N3—C35—H35	118.4
C15—C14—H14	119.6	C33—C35—H35	118.4
C14—C15—C16	118.7 (2)	N3—C36—C37	113.1 (2)
C14—C15—C17	120.3 (2)	N3—C36—H36A	109.0
C16—C15—C17	120.9 (2)	C37—C36—H36A	109.0
O2—C16—C11	118.4 (2)	N3—C36—H36B	109.0
O2—C16—C15	121.8 (2)	C37—C36—H36B	109.0
C11—C16—C15	119.8 (2)	H36A—C36—H36B	107.8
N1—C17—C15	122.3 (2)	C36—C37—C18	109.1 (2)
N1—C17—H17	118.8	C36—C37—C27	111.42 (19)
C15—C17—H17	118.8	C18—C37—C27	107.39 (18)
N1—C18—C37	111.7 (2)	C36—C37—C9	108.6 (2)
N1—C18—H18A	109.3	C18—C37—C9	110.63 (19)
C37—C18—H18A	109.3	C27—C37—C9	109.64 (19)
N1—C18—H18B	109.3	C17—N1—C18	119.5 (2)
C37—C18—H18B	109.3	C26—N2—C27	116.9 (2)
H18A—C18—H18B	107.9	C35—N3—C36	117.2 (2)
O8—C19—H19A	109.5	C8—N4—C9	120.7 (2)
O8—C19—H19B	109.5	C11—O1—C10	118.6 (2)
H19A—C19—H19B	109.5	C16—O2—H2	109.5
O8—C19—H19C	109.5	C2—O3—C1	118.8 (2)
H19A—C19—H19C	109.5	C7—O4—H4	109.5
H19B—C19—H19C	109.5	C29—O5—C28	118.0 (2)
O8—C20—C21	125.5 (3)	C34—O6—H6	109.5
O8—C20—C25	115.1 (3)	C25—O7—H7	109.5
C21—C20—C25	119.3 (3)	C20—O8—C19	117.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.592 (3)	147
O4—H4···N4	0.82	1.84	2.567 (2)	147
O6—H6···N3	0.82	1.89	2.623 (3)	148
O7—H7···N2	0.82	1.88	2.612 (3)	148
C27—H27B···N1	0.97	2.56	2.936 (3)	103
C26—H26···O5i	0.93	2.58	3.309 (3)	136
C28—H28C···O2i	0.96	2.57	3.387 (3)	143
C12—H12···O6ii	0.93	2.59	3.400 (3)	146
C32—H32···O3iii	0.93	2.42	3.289 (3)	155
C36—H36B···O8iv	0.97	2.55	3.399 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.87	2.592 (3)	147
O4—H4⋯N4	0.82	1.84	2.567 (2)	147
O6—H6⋯N3	0.82	1.89	2.623 (3)	148
O7—H7⋯N2	0.82	1.88	2.612 (3)	148
C27—H27B⋯N1	0.97	2.56	2.936 (3)	103
C26—H26⋯O5i	0.93	2.58	3.309 (3)	136
C28—H28C⋯O2i	0.96	2.57	3.387 (3)	143
C12—H12⋯O6ii	0.93	2.59	3.400 (3)	146
C32—H32⋯O3iii	0.93	2.42	3.289 (3)	155
C36—H36B⋯O8iv	0.97	2.55	3.399 (3)	146

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