3-{[1-(2,3,5-Tri-O-benzoyl-β-d-ribofur-an-os-1-yl)-1H-1,2,3-triazol-4-yl]meth-yl}quin-a-zolin-4(3H)-one.

In the compound, C(37)H(29)N(5)O(8), the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the mol-ecules are linked by non-classical C-H⋯N and C-H⋯O hydrogen bonds, building an infinite three-dimensional network.

Related literature

For details of the synthesis, see: Ines et al. (2008 ▶); Krim et al. (2009 ▶); Huisgen (1963 ▶), Wu et al. (2004 ▶). For background to the biological activity of quinazolines, see: Traxler (1998 ▶); Bridges (2001 ▶); Wakeling (2005 ▶); Diana & Nitz (1993 ▶); Chen et al. (2000 ▶); Manfredini et al. (2000 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C37H29N5O8

M = 671.65

Monoclinic,

a = 11.2646 (2) Å

b = 5.6471 (1) Å

c = 25.7507 (4) Å

β = 99.595 (1)°

V = 1615.15 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.33 × 0.29 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer

26180 measured reflections

4490 independent reflections

3651 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 1.03

4490 reflections

451 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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,1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042778/bt6845sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042778/bt6845Isup2.hkl

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

C37H29N5O8	F(000) = 700
Mr = 671.65	Dx = 1.381 Mg m−3
Monoclinic, P21	Melting point: 454 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.2646 (2) Å	Cell parameters from 4490 reflections
b = 5.6471 (1) Å	θ = 0.8–28.5°
c = 25.7507 (4) Å	µ = 0.10 mm−1
β = 99.595 (1)°	T = 296 K
V = 1615.15 (5) Å3	Block, colourless
Z = 2	0.33 × 0.29 × 0.25 mm

Bruker X8 APEXII diffractometer	3651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.5°, θmin = 0.8°
φ and ω scans	h = −15→13
26180 measured reflections	k = −6→7
4490 independent reflections	l = −32→34

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.1513P] where P = (Fo2 + 2Fc2)/3
4490 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.48779 (13)	0.5193 (3)	0.77079 (5)	0.0599 (4)
C1	1.47437 (15)	0.5402 (3)	0.81663 (7)	0.0394 (4)
C2	1.52690 (15)	0.3864 (4)	0.85969 (7)	0.0409 (4)
C3	1.60106 (17)	0.1978 (4)	0.85044 (9)	0.0527 (5)
H3	1.6160	0.1675	0.8166	0.063*
C4	1.6516 (2)	0.0575 (5)	0.89200 (12)	0.0715 (7)
H4	1.7013	−0.0682	0.8863	0.086*
C5	1.6288 (2)	0.1029 (6)	0.94223 (11)	0.0803 (8)
H5	1.6638	0.0073	0.9700	0.096*
C6	1.5565 (2)	0.2845 (6)	0.95168 (9)	0.0702 (7)
H6	1.5421	0.3122	0.9857	0.084*
C7	1.50357 (18)	0.4298 (4)	0.91030 (8)	0.0491 (5)
N1	1.42881 (18)	0.6125 (4)	0.92126 (7)	0.0596 (5)
N2	1.40433 (13)	0.7224 (3)	0.83175 (6)	0.0419 (3)
C8	1.38486 (19)	0.7462 (4)	0.88269 (8)	0.0545 (5)
H8	1.3355	0.8701	0.8898	0.065*
C9	1.35481 (18)	0.8972 (4)	0.79210 (8)	0.0517 (5)
H9A	1.4119	0.9228	0.7683	0.062*
H9B	1.3444	1.0464	0.8095	0.062*
C10	1.23629 (16)	0.8228 (3)	0.76079 (7)	0.0407 (4)
C11	1.18997 (17)	0.6052 (4)	0.74762 (8)	0.0445 (4)
H11	1.2253	0.4588	0.7566	0.053*
N3	1.15628 (14)	0.9885 (3)	0.73967 (6)	0.0439 (4)
N4	1.06111 (14)	0.8827 (3)	0.71381 (7)	0.0456 (4)
N5	1.08115 (13)	0.6486 (3)	0.71851 (6)	0.0392 (3)
C12	0.98816 (16)	0.4739 (3)	0.69944 (7)	0.0396 (4)
H12	1.0233	0.3450	0.6815	0.048*
O2	0.93768 (11)	0.3821 (3)	0.74159 (5)	0.0486 (3)
C13	0.81906 (16)	0.4779 (4)	0.74176 (7)	0.0441 (4)
H13	0.7602	0.3536	0.7298	0.053*
C14	0.80732 (18)	0.5416 (5)	0.79708 (8)	0.0529 (5)
H14A	0.7273	0.6033	0.7979	0.063*
H14B	0.8185	0.4013	0.8191	0.063*
C15	0.92262 (17)	0.7284 (4)	0.87000 (7)	0.0495 (5)
O3	0.89576 (12)	0.7166 (3)	0.81724 (5)	0.0523 (4)
O4	0.87382 (16)	0.6050 (4)	0.89822 (6)	0.0759 (5)
C16	1.01456 (17)	0.9096 (4)	0.88883 (7)	0.0482 (5)
C17	1.05099 (19)	1.0778 (4)	0.85589 (8)	0.0537 (5)
H17	1.0199	1.0759	0.8201	0.064*
C18	1.1337 (2)	1.2490 (5)	0.87610 (10)	0.0701 (7)
H18	1.1572	1.3638	0.8540	0.084*
C19	1.1811 (2)	1.2495 (6)	0.92904 (10)	0.0770 (8)
H19	1.2372	1.3641	0.9425	0.092*
C20	1.1460 (3)	1.0813 (7)	0.96195 (10)	0.0810 (8)
H20	1.1786	1.0821	0.9976	0.097*
C21	1.0629 (2)	0.9123 (6)	0.94236 (8)	0.0688 (7)
H21	1.0389	0.7995	0.9648	0.083*
C22	0.80514 (15)	0.6720 (3)	0.70008 (7)	0.0388 (4)
H22	0.8349	0.8231	0.7158	0.047*
O5	0.68225 (11)	0.6958 (2)	0.67425 (5)	0.0454 (3)
O6	0.65640 (13)	0.9904 (3)	0.72934 (6)	0.0625 (4)
C23	0.61705 (16)	0.8669 (4)	0.69278 (7)	0.0420 (4)
C24	0.49230 (16)	0.8815 (4)	0.66316 (7)	0.0440 (4)
C25	0.4252 (2)	1.0813 (5)	0.67048 (9)	0.0592 (6)
H25	0.4599	1.2044	0.6918	0.071*
C26	0.3065 (2)	1.0963 (6)	0.64598 (11)	0.0767 (9)
H26	0.2615	1.2304	0.6506	0.092*
C27	0.2555 (2)	0.9163 (7)	0.61522 (12)	0.0833 (10)
H27	0.1751	0.9266	0.5995	0.100*
C28	0.3214 (2)	0.7190 (7)	0.60707 (11)	0.0827 (9)
H28	0.2860	0.5976	0.5855	0.099*
C29	0.4405 (2)	0.7013 (5)	0.63111 (9)	0.0620 (6)
H29	0.4855	0.5682	0.6256	0.074*
C30	0.88453 (15)	0.5871 (4)	0.66172 (7)	0.0400 (4)
H30	0.9110	0.7159	0.6408	0.048*
O7	0.82166 (11)	0.4025 (3)	0.62974 (5)	0.0452 (3)
O8	0.97436 (13)	0.3887 (4)	0.58366 (6)	0.0704 (5)
C31	0.87760 (18)	0.3172 (4)	0.59115 (8)	0.0494 (5)
C32	0.80817 (18)	0.1250 (4)	0.56099 (7)	0.0486 (5)
C33	0.6908 (2)	0.0733 (5)	0.56586 (9)	0.0645 (6)
H33	0.6516	0.1623	0.5883	0.077*
C34	0.6317 (3)	−0.1120 (6)	0.53723 (10)	0.0793 (8)
H34	0.5524	−0.1467	0.5402	0.095*
C35	0.6900 (3)	−0.2449 (6)	0.50442 (10)	0.0794 (8)
H35	0.6503	−0.3700	0.4854	0.095*
C36	0.8059 (3)	−0.1932 (6)	0.49975 (10)	0.0810 (9)
H36	0.8450	−0.2836	0.4776	0.097*
C37	0.8650 (2)	−0.0097 (6)	0.52735 (9)	0.0666 (7)
H37	0.9438	0.0251	0.5236	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0670 (9)	0.0774 (11)	0.0363 (7)	0.0054 (9)	0.0121 (6)	0.0024 (7)
C1	0.0354 (9)	0.0417 (10)	0.0403 (9)	−0.0081 (8)	0.0036 (7)	−0.0004 (8)
C2	0.0346 (8)	0.0445 (10)	0.0420 (9)	−0.0090 (8)	0.0021 (7)	0.0018 (8)
C3	0.0383 (10)	0.0541 (13)	0.0657 (13)	−0.0055 (9)	0.0085 (9)	−0.0017 (11)
C4	0.0495 (12)	0.0572 (15)	0.105 (2)	0.0085 (11)	0.0051 (12)	0.0176 (15)
C5	0.0767 (16)	0.082 (2)	0.0746 (17)	0.0064 (16)	−0.0094 (13)	0.0320 (16)
C6	0.0818 (16)	0.0797 (18)	0.0457 (12)	−0.0010 (15)	0.0006 (11)	0.0169 (13)
C7	0.0509 (11)	0.0548 (13)	0.0394 (10)	−0.0091 (10)	0.0012 (8)	0.0036 (9)
N1	0.0744 (12)	0.0659 (12)	0.0388 (9)	0.0013 (11)	0.0105 (8)	−0.0050 (9)
N2	0.0447 (8)	0.0390 (8)	0.0394 (8)	−0.0056 (7)	−0.0005 (6)	0.0015 (7)
C8	0.0628 (12)	0.0528 (13)	0.0472 (11)	0.0010 (11)	0.0075 (9)	−0.0084 (10)
C9	0.0548 (11)	0.0391 (11)	0.0561 (12)	−0.0088 (10)	−0.0059 (9)	0.0077 (9)
C10	0.0464 (10)	0.0327 (10)	0.0417 (10)	−0.0007 (8)	0.0032 (8)	0.0027 (8)
C11	0.0437 (10)	0.0319 (9)	0.0529 (11)	0.0057 (8)	−0.0068 (8)	0.0032 (9)
N3	0.0439 (8)	0.0296 (7)	0.0580 (10)	0.0008 (7)	0.0074 (7)	0.0036 (7)
N4	0.0409 (8)	0.0308 (8)	0.0638 (10)	0.0030 (7)	0.0050 (7)	0.0048 (8)
N5	0.0400 (8)	0.0290 (8)	0.0467 (8)	0.0026 (6)	0.0018 (6)	0.0008 (6)
C12	0.0410 (9)	0.0318 (9)	0.0445 (10)	0.0010 (8)	0.0027 (7)	−0.0018 (8)
O2	0.0480 (7)	0.0437 (7)	0.0533 (8)	0.0039 (7)	0.0059 (6)	0.0130 (7)
C13	0.0394 (9)	0.0440 (10)	0.0472 (10)	−0.0087 (9)	0.0022 (7)	0.0005 (9)
C14	0.0479 (10)	0.0664 (14)	0.0444 (10)	−0.0136 (10)	0.0075 (8)	0.0057 (10)
C15	0.0486 (10)	0.0630 (13)	0.0374 (10)	0.0065 (10)	0.0088 (8)	0.0042 (10)
O3	0.0546 (8)	0.0639 (9)	0.0369 (7)	−0.0138 (7)	0.0028 (6)	0.0009 (7)
O4	0.0871 (11)	0.0960 (14)	0.0462 (8)	−0.0236 (12)	0.0156 (8)	0.0069 (10)
C16	0.0489 (10)	0.0554 (12)	0.0395 (10)	0.0059 (10)	0.0048 (8)	−0.0042 (9)
C17	0.0584 (12)	0.0580 (13)	0.0451 (11)	0.0031 (11)	0.0095 (9)	−0.0044 (10)
C18	0.0831 (16)	0.0657 (16)	0.0636 (15)	−0.0101 (14)	0.0185 (12)	−0.0084 (13)
C19	0.0741 (16)	0.088 (2)	0.0684 (16)	−0.0170 (16)	0.0097 (13)	−0.0245 (16)
C20	0.0841 (17)	0.106 (2)	0.0478 (13)	−0.0097 (18)	−0.0033 (12)	−0.0182 (16)
C21	0.0778 (15)	0.0861 (19)	0.0405 (11)	−0.0056 (15)	0.0037 (10)	0.0000 (12)
C22	0.0349 (8)	0.0389 (10)	0.0408 (9)	0.0000 (8)	0.0009 (7)	−0.0039 (8)
O5	0.0380 (6)	0.0471 (8)	0.0482 (7)	0.0065 (6)	−0.0011 (5)	−0.0111 (6)
O6	0.0558 (8)	0.0545 (9)	0.0761 (10)	−0.0015 (8)	0.0079 (7)	−0.0252 (9)
C23	0.0429 (9)	0.0365 (10)	0.0474 (10)	−0.0012 (8)	0.0098 (8)	−0.0019 (9)
C24	0.0411 (9)	0.0481 (11)	0.0443 (10)	0.0030 (9)	0.0116 (8)	0.0094 (9)
C25	0.0582 (12)	0.0618 (14)	0.0616 (13)	0.0162 (12)	0.0215 (10)	0.0190 (12)
C26	0.0622 (15)	0.095 (2)	0.0780 (17)	0.0330 (16)	0.0267 (13)	0.0387 (17)
C27	0.0468 (13)	0.123 (3)	0.0780 (18)	0.0130 (17)	0.0044 (12)	0.048 (2)
C28	0.0629 (15)	0.095 (2)	0.0812 (18)	−0.0118 (16)	−0.0149 (13)	0.0114 (17)
C29	0.0522 (12)	0.0651 (15)	0.0647 (14)	−0.0008 (12)	−0.0019 (10)	0.0026 (12)
C30	0.0417 (9)	0.0388 (10)	0.0385 (9)	0.0017 (8)	0.0040 (7)	−0.0005 (8)
O7	0.0436 (7)	0.0520 (8)	0.0394 (7)	−0.0014 (6)	0.0051 (5)	−0.0093 (6)
O8	0.0559 (9)	0.0925 (13)	0.0672 (10)	−0.0132 (10)	0.0234 (7)	−0.0204 (10)
C31	0.0494 (11)	0.0585 (13)	0.0404 (10)	0.0063 (10)	0.0076 (8)	−0.0048 (9)
C32	0.0521 (11)	0.0568 (12)	0.0355 (9)	0.0057 (10)	0.0034 (8)	−0.0033 (9)
C33	0.0683 (14)	0.0726 (16)	0.0567 (13)	−0.0108 (13)	0.0225 (11)	−0.0148 (13)
C34	0.0811 (17)	0.089 (2)	0.0725 (16)	−0.0296 (17)	0.0256 (14)	−0.0197 (16)
C35	0.102 (2)	0.0711 (18)	0.0631 (15)	−0.0160 (17)	0.0086 (14)	−0.0229 (14)
C36	0.0784 (17)	0.096 (2)	0.0663 (15)	0.0148 (16)	0.0043 (13)	−0.0357 (16)
C37	0.0544 (12)	0.0889 (19)	0.0549 (13)	0.0114 (13)	0.0043 (10)	−0.0217 (13)

O1—C1	1.220 (2)	C17—C18	1.383 (3)
C1—N2	1.391 (2)	C17—H17	0.9300
C1—C2	1.455 (3)	C18—C19	1.379 (4)
C2—C7	1.394 (3)	C18—H18	0.9300
C2—C3	1.398 (3)	C19—C20	1.374 (4)
C3—C4	1.376 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.373 (4)
C4—C5	1.384 (4)	C20—H20	0.9300
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.357 (4)	C22—O5	1.439 (2)
C5—H5	0.9300	C22—C30	1.517 (2)
C6—C7	1.397 (3)	C22—H22	0.9800
C6—H6	0.9300	O5—C23	1.348 (2)
C7—N1	1.390 (3)	O6—C23	1.196 (2)
N1—C8	1.280 (3)	C23—C24	1.485 (3)
N2—C8	1.372 (2)	C24—C29	1.377 (3)
N2—C9	1.462 (3)	C24—C25	1.388 (3)
C8—H8	0.9300	C25—C26	1.383 (3)
C9—C10	1.500 (3)	C25—H25	0.9300
C9—H9A	0.9700	C26—C27	1.356 (5)
C9—H9B	0.9700	C26—H26	0.9300
C10—N3	1.349 (2)	C27—C28	1.374 (5)
C10—C11	1.356 (3)	C27—H27	0.9300
C11—N5	1.348 (2)	C28—C29	1.385 (3)
C11—H11	0.9300	C28—H28	0.9300
N3—N4	1.308 (2)	C29—H29	0.9300
N4—N5	1.343 (2)	C30—O7	1.439 (2)
N5—C12	1.463 (2)	C30—H30	0.9800
C12—O2	1.406 (2)	O7—C31	1.351 (2)
C12—C30	1.529 (2)	O8—C31	1.207 (2)
C12—H12	0.9800	C31—C32	1.480 (3)
O2—C13	1.442 (2)	C32—C33	1.380 (3)
C13—C14	1.496 (3)	C32—C37	1.387 (3)
C13—C22	1.524 (3)	C33—C34	1.385 (4)
C13—H13	0.9800	C33—H33	0.9300
C14—O3	1.437 (3)	C34—C35	1.376 (4)
C14—H14A	0.9700	C34—H34	0.9300
C14—H14B	0.9700	C35—C36	1.362 (4)
C15—O4	1.204 (3)	C35—H35	0.9300
C15—O3	1.343 (2)	C36—C37	1.365 (4)
C15—C16	1.479 (3)	C36—H36	0.9300
C16—C17	1.381 (3)	C37—H37	0.9300
C16—C21	1.395 (3)
O1—C1—N2	120.65 (17)	C16—C17—C18	120.0 (2)
O1—C1—C2	125.40 (18)	C16—C17—H17	120.0
N2—C1—C2	113.95 (16)	C18—C17—H17	120.0
C7—C2—C3	120.29 (19)	C19—C18—C17	120.0 (3)
C7—C2—C1	119.44 (18)	C19—C18—H18	120.0
C3—C2—C1	120.26 (18)	C17—C18—H18	120.0
C4—C3—C2	119.2 (2)	C20—C19—C18	120.3 (3)
C4—C3—H3	120.4	C20—C19—H19	119.9
C2—C3—H3	120.4	C18—C19—H19	119.9
C3—C4—C5	120.2 (2)	C21—C20—C19	120.2 (2)
C3—C4—H4	119.9	C21—C20—H20	119.9
C5—C4—H4	119.9	C19—C20—H20	119.9
C6—C5—C4	121.2 (2)	C20—C21—C16	120.1 (3)
C6—C5—H5	119.4	C20—C21—H21	120.0
C4—C5—H5	119.4	C16—C21—H21	120.0
C5—C6—C7	120.0 (2)	O5—C22—C30	110.78 (13)
C5—C6—H6	120.0	O5—C22—C13	111.78 (15)
C7—C6—H6	120.0	C30—C22—C13	103.22 (16)
N1—C7—C2	122.38 (18)	O5—C22—H22	110.3
N1—C7—C6	118.5 (2)	C30—C22—H22	110.3
C2—C7—C6	119.1 (2)	C13—C22—H22	110.3
C8—N1—C7	116.71 (17)	C23—O5—C22	116.25 (14)
C8—N2—C1	121.92 (17)	O6—C23—O5	122.97 (17)
C8—N2—C9	119.88 (18)	O6—C23—C24	124.52 (18)
C1—N2—C9	118.16 (16)	O5—C23—C24	112.50 (16)
N1—C8—N2	125.5 (2)	C29—C24—C25	119.8 (2)
N1—C8—H8	117.2	C29—C24—C23	122.45 (19)
N2—C8—H8	117.2	C25—C24—C23	117.7 (2)
N2—C9—C10	112.83 (17)	C26—C25—C24	119.7 (3)
N2—C9—H9A	109.0	C26—C25—H25	120.2
C10—C9—H9A	109.0	C24—C25—H25	120.2
N2—C9—H9B	109.0	C27—C26—C25	120.3 (3)
C10—C9—H9B	109.0	C27—C26—H26	119.9
H9A—C9—H9B	107.8	C25—C26—H26	119.9
N3—C10—C11	108.93 (16)	C26—C27—C28	120.6 (2)
N3—C10—C9	119.82 (17)	C26—C27—H27	119.7
C11—C10—C9	131.24 (18)	C28—C27—H27	119.7
N5—C11—C10	104.50 (17)	C27—C28—C29	119.9 (3)
N5—C11—H11	127.7	C27—C28—H28	120.1
C10—C11—H11	127.7	C29—C28—H28	120.1
N4—N3—C10	108.91 (16)	C24—C29—C28	119.8 (3)
N3—N4—N5	107.01 (15)	C24—C29—H29	120.1
N4—N5—C11	110.65 (16)	C28—C29—H29	120.1
N4—N5—C12	122.23 (15)	O7—C30—C22	108.31 (14)
C11—N5—C12	126.70 (16)	O7—C30—C12	108.15 (15)
O2—C12—N5	110.41 (14)	C22—C30—C12	100.90 (14)
O2—C12—C30	106.29 (14)	O7—C30—H30	112.9
N5—C12—C30	111.07 (15)	C22—C30—H30	112.9
O2—C12—H12	109.7	C12—C30—H30	112.9
N5—C12—H12	109.7	C31—O7—C30	115.70 (15)
C30—C12—H12	109.7	O8—C31—O7	122.9 (2)
C12—O2—C13	110.98 (14)	O8—C31—C32	124.97 (19)
O2—C13—C14	108.78 (15)	O7—C31—C32	112.15 (17)
O2—C13—C22	104.75 (14)	C33—C32—C37	119.3 (2)
C14—C13—C22	118.86 (19)	C33—C32—C31	122.55 (19)
O2—C13—H13	108.0	C37—C32—C31	118.14 (19)
C14—C13—H13	108.0	C32—C33—C34	119.6 (2)
C22—C13—H13	108.0	C32—C33—H33	120.2
O3—C14—C13	110.08 (15)	C34—C33—H33	120.2
O3—C14—H14A	109.6	C35—C34—C33	120.2 (2)
C13—C14—H14A	109.6	C35—C34—H34	119.9
O3—C14—H14B	109.6	C33—C34—H34	119.9
C13—C14—H14B	109.6	C36—C35—C34	120.0 (3)
H14A—C14—H14B	108.2	C36—C35—H35	120.0
O4—C15—O3	122.2 (2)	C34—C35—H35	120.0
O4—C15—C16	124.62 (18)	C35—C36—C37	120.5 (2)
O3—C15—C16	113.16 (17)	C35—C36—H36	119.7
C15—O3—C14	115.17 (16)	C37—C36—H36	119.7
C17—C16—C21	119.5 (2)	C36—C37—C32	120.4 (2)
C17—C16—C15	122.56 (17)	C36—C37—H37	119.8
C21—C16—C15	117.9 (2)	C32—C37—H37	119.8
O1—C1—C2—C7	−179.64 (19)	O3—C15—C16—C21	−170.2 (2)
N2—C1—C2—C7	0.4 (2)	C21—C16—C17—C18	−0.8 (3)
O1—C1—C2—C3	0.9 (3)	C15—C16—C17—C18	177.3 (2)
N2—C1—C2—C3	−178.99 (16)	C16—C17—C18—C19	1.0 (4)
C7—C2—C3—C4	−0.7 (3)	C17—C18—C19—C20	−0.5 (4)
C1—C2—C3—C4	178.7 (2)	C18—C19—C20—C21	−0.3 (5)
C2—C3—C4—C5	0.2 (4)	C19—C20—C21—C16	0.5 (4)
C3—C4—C5—C6	0.2 (4)	C17—C16—C21—C20	0.0 (4)
C4—C5—C6—C7	−0.1 (4)	C15—C16—C21—C20	−178.1 (2)
C3—C2—C7—N1	−178.85 (19)	O2—C13—C22—O5	147.77 (14)
C1—C2—C7—N1	1.7 (3)	C14—C13—C22—O5	−90.54 (19)
C3—C2—C7—C6	0.8 (3)	O2—C13—C22—C30	28.67 (18)
C1—C2—C7—C6	−178.6 (2)	C14—C13—C22—C30	150.35 (16)
C5—C6—C7—N1	179.3 (2)	C30—C22—O5—C23	−148.57 (16)
C5—C6—C7—C2	−0.4 (4)	C13—C22—O5—C23	96.90 (19)
C2—C7—N1—C8	−2.3 (3)	C22—O5—C23—O6	−1.7 (3)
C6—C7—N1—C8	178.0 (2)	C22—O5—C23—C24	178.91 (16)
O1—C1—N2—C8	178.11 (19)	O6—C23—C24—C29	−162.5 (2)
C2—C1—N2—C8	−2.0 (2)	O5—C23—C24—C29	16.9 (3)
O1—C1—N2—C9	−4.4 (3)	O6—C23—C24—C25	14.6 (3)
C2—C1—N2—C9	175.55 (15)	O5—C23—C24—C25	−166.00 (16)
C7—N1—C8—N2	0.8 (3)	C29—C24—C25—C26	0.7 (3)
C1—N2—C8—N1	1.5 (3)	C23—C24—C25—C26	−176.40 (19)
C9—N2—C8—N1	−176.0 (2)	C24—C25—C26—C27	0.4 (3)
C8—N2—C9—C10	−95.6 (2)	C25—C26—C27—C28	−1.3 (4)
C1—N2—C9—C10	86.8 (2)	C26—C27—C28—C29	1.0 (4)
N2—C9—C10—N3	152.32 (18)	C25—C24—C29—C28	−1.0 (3)
N2—C9—C10—C11	−28.9 (3)	C23—C24—C29—C28	176.0 (2)
N3—C10—C11—N5	−0.2 (2)	C27—C28—C29—C24	0.1 (4)
C9—C10—C11—N5	−179.07 (19)	O5—C22—C30—O7	−42.7 (2)
C11—C10—N3—N4	0.2 (2)	C13—C22—C30—O7	77.08 (16)
C9—C10—N3—N4	179.22 (17)	O5—C22—C30—C12	−156.17 (15)
C10—N3—N4—N5	−0.1 (2)	C13—C22—C30—C12	−36.37 (17)
N3—N4—N5—C11	0.0 (2)	O2—C12—C30—O7	−81.39 (17)
N3—N4—N5—C12	173.02 (15)	N5—C12—C30—O7	158.48 (14)
C10—C11—N5—N4	0.1 (2)	O2—C12—C30—C22	32.19 (18)
C10—C11—N5—C12	−172.54 (17)	N5—C12—C30—C22	−87.95 (17)
N4—N5—C12—O2	−101.9 (2)	C22—C30—O7—C31	176.14 (16)
C11—N5—C12—O2	70.0 (2)	C12—C30—O7—C31	−75.31 (19)
N4—N5—C12—C30	15.8 (2)	C30—O7—C31—O8	0.3 (3)
C11—N5—C12—C30	−172.38 (17)	C30—O7—C31—C32	178.77 (15)
N5—C12—O2—C13	105.43 (16)	O8—C31—C32—C33	−170.3 (2)
C30—C12—O2—C13	−15.1 (2)	O7—C31—C32—C33	11.3 (3)
C12—O2—C13—C14	−136.61 (18)	O8—C31—C32—C37	10.9 (3)
C12—O2—C13—C22	−8.5 (2)	O7—C31—C32—C37	−167.5 (2)
O2—C13—C14—O3	60.5 (2)	C37—C32—C33—C34	0.1 (4)
C22—C13—C14—O3	−59.1 (2)	C31—C32—C33—C34	−178.7 (2)
O4—C15—O3—C14	−1.7 (3)	C32—C33—C34—C35	0.5 (4)
C16—C15—O3—C14	179.56 (18)	C33—C34—C35—C36	−0.5 (5)
C13—C14—O3—C15	−157.97 (19)	C34—C35—C36—C37	−0.1 (5)
O4—C15—C16—C17	−167.0 (2)	C35—C36—C37—C32	0.7 (4)
O3—C15—C16—C17	11.7 (3)	C33—C32—C37—C36	−0.7 (4)
O4—C15—C16—C21	11.1 (3)	C31—C32—C37—C36	178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6i	0.93	2.57	3.483 (3)	168
C13—H13···O6ii	0.98	2.36	3.293 (3)	159
C6—H6···N1iii	0.93	2.62	3.390 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6i	0.93	2.57	3.483 (3)	168
C13—H13⋯O6ii	0.98	2.36	3.293 (3)	159
C6—H6⋯N1iii	0.93	2.62	3.390 (3)	141

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