3,3'-Diphenyl-1,1'-[2,2'-oxybis(2,1-phenyl-ene)]diurea N,N-dimethyl-formamide disolvate.

In the structure of the title compound, C(26)H(22)N(4)O(3)·2C(3)H(7)NO, one of the DMF solvent mol-ecules is disordered over two sets of positions in a 0.5:0.5 ratio. In the 1,1'-[2,2'-oxybis(2,1-phenyl-ene)]bis-(3-phenyl-urea) mol-ecule, the two diphenyl-urea segments are linked via an ether O atom and are inclined at an angle of 53.80 (4)° to one another. In the crystal structure, classical N-H⋯O hydrogen bonds link each mol-ecule to two DMF solvent mol-ecules and these aggregates form columns down a through C-H⋯π inter-actions. Additional C-H⋯O inter-actions link the main mol-ecule and the solvent mol-ecules, forming columns of independent zigzag chains along b.

Related literature

For information on anion binding agents, see: Gunnlaugsson et al. (2004 ▶); Kim & Kim (2005 ▶). To our knowledge, no structures of oxybis(phenyl­ene)phenyl­urea derivatives have been reported previously. However, for structures of N,N′-diphenyl­thio­n class="Chemical">urea, see: Dannecker et al. (1979 ▶); Galkin et al. (2006 ▶). For structures of oxybis(amino­benzene) derivatives, see: Bensemann et al. (2003 ▶); Ashton et al. (1996 ▶).

Experimental

Crystal data

C26H22N4O3·2C3H7NO

M = 584.67

Monoclinic,

a = 11.1035 (2) Å

b = 8.1564 (2) Å

c = 16.8881 (3) Å

β = 103.429 (1)°

V = 1487.65 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 180 (2) K

0.46 × 0.35 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.905, T max = 0.979

16291 measured reflections

3643 independent reflections

3337 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.04

3643 reflections

385 parameters

25 restraints

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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: SHELXL97, enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066548/hb2678sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066548/hb2678Isup2.hkl

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

C26H22N4O3·2(C3H7NO)	F000 = 620
Mr = 584.67	Dx = 1.305 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11759 reflections
a = 11.1035 (2) Å	θ = 1.0–27.5º
b = 8.1564 (2) Å	µ = 0.09 mm−1
c = 16.8881 (3) Å	T = 180 (2) K
β = 103.429 (1)º	Block, colourless
V = 1487.65 (5) Å3	0.46 × 0.35 × 0.23 mm
Z = 2

Nonius KappaCCD diffractometer	3337 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
T = 180(2) K	θmax = 27.5º
Thin–slice ω and φ scans	θmin = 3.5º
Absorption correction: multi-scan(SORTAV; Blessing, 1995)	h = −14→14
Tmin = 0.905, Tmax = 0.979	k = −9→10
16291 measured reflections	l = −21→21
3643 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0791P)2 + 0.5832P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3643 reflections	Δρmax = 0.79 e Å−3
385 parameters	Δρmin = −0.36 e Å−3
25 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (6)

Experimental. One of the DMF solvate molecules is disordered over two sites: common, isotropic temperature factors were applied to the non-H atoms of this moiety.

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	Occ. (<1)
N1	0.0475 (2)	0.8656 (4)	0.19863 (16)	0.0384 (6)
H1N	0.1190	0.8925	0.1882	0.046*
O1	−0.0703 (2)	0.9052 (4)	0.29150 (15)	0.0546 (7)
C1	−0.1737 (3)	0.5733 (5)	0.0162 (2)	0.0487 (8)
H1	−0.2225	0.5077	−0.0257	0.058*
N2	0.1272 (2)	1.0072 (3)	0.31451 (15)	0.0343 (6)
H2N	0.1937	1.0089	0.2946	0.041*
O2	0.33284 (17)	1.1674 (3)	0.37323 (11)	0.0365 (5)
C2	−0.2174 (3)	0.6157 (4)	0.0830 (2)	0.0436 (8)
H2	−0.2966	0.5780	0.0872	0.052*
O3	0.56816 (19)	1.4761 (4)	0.21808 (13)	0.0506 (7)
N3	0.4261 (2)	1.3857 (4)	0.28714 (16)	0.0381 (6)
H3N	0.3461	1.3781	0.2841	0.046*
C3	−0.1478 (3)	0.7131 (4)	0.14500 (19)	0.0385 (7)
H3	−0.1798	0.7421	0.1906	0.046*
N4	0.3619 (2)	1.4974 (4)	0.16115 (17)	0.0446 (7)
H4N	0.2880	1.4767	0.1694	0.054*
C4	−0.0314 (3)	0.7675 (4)	0.13956 (17)	0.0327 (6)
C5	0.0135 (3)	0.7227 (4)	0.07149 (19)	0.0409 (7)
H5	0.0933	0.7583	0.0674	0.049*
C6	−0.0570 (3)	0.6275 (5)	0.0104 (2)	0.0491 (8)
H6	−0.0260	0.5988	−0.0356	0.059*
C7	0.0261 (3)	0.9232 (4)	0.26955 (18)	0.0348 (6)
C8	0.1356 (2)	1.0902 (4)	0.38836 (16)	0.0305 (6)
C9	0.0432 (3)	1.0957 (4)	0.43132 (18)	0.0367 (6)
H9	−0.0329	1.0401	0.4108	0.044*
C10	0.0610 (3)	1.1817 (5)	0.50385 (19)	0.0435 (8)
H10	−0.0032	1.1842	0.5325	0.052*
C11	0.1701 (3)	1.2635 (5)	0.53523 (18)	0.0418 (7)
H11	0.1814	1.3211	0.5853	0.050*
C12	0.2634 (3)	1.2609 (4)	0.49290 (18)	0.0359 (6)
H12	0.3386	1.3183	0.5134	0.043*
C13	0.2462 (2)	1.1743 (4)	0.42062 (16)	0.0297 (5)
C14	0.4548 (2)	1.2147 (4)	0.40545 (17)	0.0312 (6)
C15	0.5259 (3)	1.1477 (4)	0.47623 (18)	0.0375 (6)
H15	0.4908	1.0705	0.5065	0.045*
C16	0.6488 (3)	1.1939 (5)	0.50276 (19)	0.0417 (7)
H16	0.6979	1.1500	0.5518	0.050*
C17	0.6997 (3)	1.3043 (5)	0.45735 (19)	0.0407 (7)
H17	0.7840	1.3358	0.4757	0.049*
C18	0.6295 (3)	1.3696 (4)	0.38541 (18)	0.0374 (6)
H18	0.6658	1.4443	0.3546	0.045*
C19	0.5055 (3)	1.3254 (4)	0.35856 (17)	0.0319 (6)
C20	0.4606 (3)	1.4552 (4)	0.22158 (18)	0.0345 (6)
C21	0.3665 (3)	1.5712 (4)	0.08639 (19)	0.0346 (6)
C22	0.4558 (3)	1.6869 (4)	0.08045 (19)	0.0391 (7)
H22	0.5172	1.7173	0.1273	0.047*
C23	0.4548 (3)	1.7576 (5)	0.0059 (2)	0.0449 (7)
H23	0.5162	1.8364	0.0021	0.054*
C24	0.3659 (3)	1.7156 (5)	−0.0634 (2)	0.0448 (8)
H24	0.3658	1.7652	−0.1143	0.054*
C25	0.2777 (3)	1.6003 (5)	−0.0568 (2)	0.0468 (8)
H25	0.2164	1.5703	−0.1038	0.056*
C26	0.2771 (3)	1.5281 (4)	0.0171 (2)	0.0417 (7)
H26	0.2157	1.4491	0.0207	0.050*
O4	0.2870 (2)	0.9862 (5)	0.19570 (14)	0.0576 (8)
N5	0.4865 (2)	0.9358 (4)	0.25860 (15)	0.0422 (6)
C27	0.3979 (3)	1.0063 (5)	0.20292 (18)	0.0436 (8)
H27	0.4227	1.0786	0.1655	0.065*
C28	0.4566 (4)	0.8214 (5)	0.3171 (2)	0.0520 (9)
H28A	0.3726	0.7790	0.2963	0.078*
H28B	0.4613	0.8778	0.3689	0.078*
H28C	0.5157	0.7303	0.3253	0.078*
C29	0.6164 (3)	0.9735 (7)	0.2665 (3)	0.0654 (12)
H29A	0.6244	1.0593	0.2274	0.098*
H29B	0.6601	0.8747	0.2556	0.098*
H29C	0.6524	1.0121	0.3219	0.098*
O5	0.1857 (6)	0.5004 (9)	0.2790 (4)	0.0671 (11)*	0.50
N6	−0.0062 (7)	0.3841 (11)	0.2555 (5)	0.0401 (9)*	0.50
C30	0.0876 (6)	0.4795 (10)	0.3014 (4)	0.0455 (11)*	0.50
H30	0.0770	0.5292	0.3502	0.055*	0.50
C31	0.0181 (8)	0.3207 (12)	0.1803 (5)	0.0566 (10)*	0.50
H31A	−0.0117	0.3992	0.1362	0.085*	0.50
H31B	−0.0251	0.2159	0.1668	0.085*	0.50
H31C	0.1073	0.3041	0.1871	0.085*	0.50
C32	−0.1324 (8)	0.3298 (12)	0.2555 (5)	0.0566 (10)*	0.50
H32A	−0.1576	0.2436	0.2146	0.085*	0.50
H32B	−0.1894	0.4229	0.2424	0.085*	0.50
H32C	−0.1343	0.2869	0.3094	0.085*	0.50
O5'	0.1596 (5)	0.3843 (9)	0.2144 (4)	0.0671 (11)*	0.50
N6'	−0.0096 (7)	0.4027 (12)	0.2653 (5)	0.0401 (9)*	0.50
C30'	0.0532 (7)	0.3524 (10)	0.2138 (5)	0.0455 (11)*	0.50
H30'	0.0108	0.2831	0.1712	0.055*	0.50
C31'	0.0366 (7)	0.5061 (11)	0.3332 (5)	0.0566 (10)*	0.50
H31D	0.1145	0.5561	0.3278	0.085*	0.50
H31E	0.0511	0.4412	0.3834	0.085*	0.50
H31F	−0.0240	0.5924	0.3353	0.085*	0.50
C32'	−0.1265 (8)	0.3719 (13)	0.2756 (5)	0.0566 (10)*	0.50
H32D	−0.1433	0.2540	0.2702	0.085*	0.50
H32E	−0.1872	0.4313	0.2342	0.085*	0.50
H32F	−0.1323	0.4086	0.3299	0.085*	0.50

	U11	U22	U33	U12	U13	U23
N1	0.0290 (11)	0.0458 (15)	0.0429 (13)	−0.0094 (11)	0.0133 (10)	−0.0104 (12)
O1	0.0420 (12)	0.0728 (19)	0.0552 (13)	−0.0216 (13)	0.0239 (11)	−0.0253 (13)
C1	0.0487 (18)	0.0443 (19)	0.0481 (18)	−0.0029 (16)	0.0009 (15)	−0.0107 (16)
N2	0.0282 (11)	0.0417 (14)	0.0357 (12)	−0.0061 (11)	0.0129 (9)	−0.0054 (11)
O2	0.0290 (9)	0.0486 (13)	0.0329 (9)	−0.0108 (10)	0.0093 (7)	−0.0012 (10)
C2	0.0309 (14)	0.0406 (18)	0.0566 (19)	−0.0002 (13)	0.0050 (13)	−0.0065 (15)
O3	0.0309 (10)	0.080 (2)	0.0430 (11)	−0.0025 (12)	0.0138 (9)	0.0070 (13)
N3	0.0253 (11)	0.0438 (15)	0.0477 (14)	0.0001 (11)	0.0136 (10)	0.0085 (13)
C3	0.0318 (13)	0.0387 (17)	0.0445 (15)	0.0010 (12)	0.0082 (12)	−0.0058 (13)
N4	0.0274 (11)	0.0579 (19)	0.0509 (15)	−0.0042 (13)	0.0138 (10)	0.0129 (14)
C4	0.0293 (13)	0.0287 (14)	0.0388 (14)	0.0008 (11)	0.0056 (11)	−0.0028 (12)
C5	0.0438 (16)	0.0362 (17)	0.0448 (16)	−0.0041 (14)	0.0149 (13)	−0.0051 (13)
C6	0.059 (2)	0.048 (2)	0.0433 (17)	−0.0045 (17)	0.0180 (15)	−0.0097 (15)
C7	0.0295 (13)	0.0336 (15)	0.0424 (15)	−0.0048 (12)	0.0104 (11)	−0.0027 (12)
C8	0.0305 (13)	0.0286 (13)	0.0329 (13)	0.0006 (11)	0.0081 (10)	0.0029 (11)
C9	0.0294 (13)	0.0417 (16)	0.0404 (15)	−0.0019 (13)	0.0111 (11)	0.0019 (13)
C10	0.0358 (14)	0.056 (2)	0.0409 (15)	0.0076 (15)	0.0140 (12)	−0.0029 (16)
C11	0.0383 (15)	0.0491 (19)	0.0377 (14)	0.0090 (14)	0.0084 (12)	−0.0040 (14)
C12	0.0320 (14)	0.0356 (15)	0.0384 (14)	0.0013 (13)	0.0046 (11)	−0.0037 (13)
C13	0.0285 (12)	0.0290 (13)	0.0322 (12)	0.0021 (11)	0.0085 (10)	0.0041 (11)
C14	0.0255 (12)	0.0305 (14)	0.0383 (13)	−0.0043 (10)	0.0088 (10)	−0.0060 (11)
C15	0.0385 (14)	0.0375 (16)	0.0372 (14)	−0.0016 (13)	0.0098 (11)	−0.0032 (13)
C16	0.0361 (15)	0.0473 (19)	0.0386 (14)	0.0044 (14)	0.0025 (12)	−0.0050 (14)
C17	0.0265 (13)	0.0485 (19)	0.0465 (16)	−0.0034 (13)	0.0069 (11)	−0.0128 (15)
C18	0.0318 (14)	0.0386 (16)	0.0443 (15)	−0.0065 (13)	0.0139 (12)	−0.0073 (14)
C19	0.0302 (13)	0.0308 (14)	0.0369 (13)	0.0012 (11)	0.0120 (11)	−0.0042 (12)
C20	0.0311 (13)	0.0339 (15)	0.0419 (15)	−0.0003 (12)	0.0153 (11)	−0.0039 (13)
C21	0.0298 (13)	0.0320 (15)	0.0445 (15)	0.0031 (11)	0.0137 (11)	0.0029 (13)
C22	0.0374 (14)	0.0390 (17)	0.0427 (15)	−0.0049 (13)	0.0130 (12)	−0.0020 (14)
C23	0.0437 (17)	0.0413 (18)	0.0542 (18)	−0.0043 (15)	0.0204 (14)	0.0034 (16)
C24	0.0440 (16)	0.0453 (19)	0.0475 (17)	0.0057 (14)	0.0155 (14)	0.0110 (15)
C25	0.0440 (17)	0.0413 (18)	0.0506 (18)	0.0042 (15)	0.0015 (14)	0.0056 (15)
C26	0.0308 (14)	0.0353 (16)	0.0566 (18)	−0.0011 (13)	0.0057 (13)	0.0050 (14)
O4	0.0337 (11)	0.097 (2)	0.0431 (12)	−0.0073 (14)	0.0105 (9)	−0.0005 (15)
N5	0.0361 (13)	0.0534 (18)	0.0373 (12)	0.0007 (13)	0.0085 (10)	−0.0056 (13)
C27	0.0353 (15)	0.065 (2)	0.0325 (14)	−0.0025 (15)	0.0118 (12)	0.0009 (15)
C28	0.071 (2)	0.0381 (18)	0.0484 (18)	0.0005 (17)	0.0160 (17)	−0.0008 (16)
C29	0.0347 (16)	0.098 (4)	0.061 (2)	0.007 (2)	0.0054 (15)	−0.007 (3)

N1—C7	1.358 (4)	C18—H18	0.9500
N1—C4	1.413 (4)	C21—C22	1.389 (4)
N1—H1N	0.8800	C21—C26	1.393 (5)
O1—C7	1.220 (4)	C22—C23	1.382 (5)
C1—C2	1.372 (5)	C22—H22	0.9500
C1—C6	1.393 (5)	C23—C24	1.387 (5)
C1—H1	0.9500	C23—H23	0.9500
N2—C7	1.383 (4)	C24—C25	1.381 (5)
N2—C8	1.403 (4)	C24—H24	0.9500
N2—H2N	0.8800	C25—C26	1.382 (5)
O2—C13	1.388 (3)	C25—H25	0.9500
O2—C14	1.392 (3)	C26—H26	0.9500
C2—C3	1.396 (4)	O4—C27	1.220 (4)
C2—H2	0.9500	N5—C27	1.324 (4)
O3—C20	1.221 (3)	N5—C29	1.450 (4)
N3—C20	1.375 (4)	N5—C28	1.452 (5)
N3—C19	1.407 (4)	C27—H27	0.9500
N3—H3N	0.8800	C28—H28A	0.9800
C3—C4	1.390 (4)	C28—H28B	0.9800
C3—H3	0.9500	C28—H28C	0.9800
N4—C20	1.357 (4)	C29—H29A	0.9800
N4—C21	1.410 (4)	C29—H29B	0.9800
N4—H4N	0.8800	C29—H29C	0.9800
C4—C5	1.403 (4)	O5—C30	1.245 (8)
C5—C6	1.380 (5)	N6—C30	1.383 (10)
C5—H5	0.9500	N6—C31	1.454 (11)
C6—H6	0.9500	N6—C32	1.469 (9)
C8—C9	1.389 (4)	C30—H30	0.9500
C8—C13	1.402 (4)	C31—H31A	0.9800
C9—C10	1.385 (5)	C31—H31B	0.9800
C9—H9	0.9500	C31—H31C	0.9800
C10—C11	1.376 (5)	C32—H32A	0.9800
C10—H10	0.9500	C32—H32B	0.9800
C11—C12	1.389 (4)	C32—H32C	0.9800
C11—H11	0.9500	O5'—C30'	1.208 (8)
C12—C13	1.385 (4)	N6'—C30'	1.301 (10)
C12—H12	0.9500	N6'—C32'	1.372 (9)
C14—C15	1.383 (4)	N6'—C31'	1.420 (10)
C14—C19	1.402 (4)	C30'—H30'	0.9500
C15—C16	1.385 (4)	C31'—H31D	0.9800
C15—H15	0.9500	C31'—H31E	0.9800
C16—C17	1.386 (5)	C31'—H31F	0.9800
C16—H16	0.9500	C32'—H32D	0.9800
C17—C18	1.389 (5)	C32'—H32E	0.9800
C17—H17	0.9500	C32'—H32F	0.9800
C18—C19	1.393 (4)
C7—N1—C4	127.7 (2)	C18—C19—C14	118.6 (3)
C7—N1—H1N	116.1	C18—C19—N3	124.3 (3)
C4—N1—H1N	116.1	C14—C19—N3	117.1 (2)
C2—C1—C6	119.3 (3)	O3—C20—N4	123.8 (3)
C2—C1—H1	120.3	O3—C20—N3	123.7 (3)
C6—C1—H1	120.3	N4—C20—N3	112.5 (2)
C7—N2—C8	127.3 (2)	C22—C21—C26	119.5 (3)
C7—N2—H2N	116.4	C22—C21—N4	122.0 (3)
C8—N2—H2N	116.4	C26—C21—N4	118.5 (3)
C13—O2—C14	120.3 (2)	C23—C22—C21	119.6 (3)
C1—C2—C3	121.3 (3)	C23—C22—H22	120.2
C1—C2—H2	119.3	C21—C22—H22	120.2
C3—C2—H2	119.3	C22—C23—C24	121.3 (3)
C20—N3—C19	126.7 (2)	C22—C23—H23	119.3
C20—N3—H3N	116.6	C24—C23—H23	119.3
C19—N3—H3N	116.6	C25—C24—C23	118.6 (3)
C4—C3—C2	119.6 (3)	C25—C24—H24	120.7
C4—C3—H3	120.2	C23—C24—H24	120.7
C2—C3—H3	120.2	C24—C25—C26	121.1 (3)
C20—N4—C21	126.2 (2)	C24—C25—H25	119.5
C20—N4—H4N	116.9	C26—C25—H25	119.5
C21—N4—H4N	116.9	C25—C26—C21	119.9 (3)
C3—C4—C5	118.9 (3)	C25—C26—H26	120.0
C3—C4—N1	124.6 (3)	C21—C26—H26	120.0
C5—C4—N1	116.5 (3)	C27—N5—C29	122.2 (3)
C6—C5—C4	120.7 (3)	C27—N5—C28	120.8 (3)
C6—C5—H5	119.6	C29—N5—C28	116.9 (3)
C4—C5—H5	119.6	O4—C27—N5	125.4 (3)
C5—C6—C1	120.1 (3)	O4—C27—H27	117.3
C5—C6—H6	120.0	N5—C27—H27	117.3
C1—C6—H6	120.0	N5—C28—H28A	109.5
O1—C7—N1	124.9 (3)	N5—C28—H28B	109.5
O1—C7—N2	123.4 (3)	H28A—C28—H28B	109.5
N1—C7—N2	111.7 (2)	N5—C28—H28C	109.5
C9—C8—C13	117.9 (3)	H28A—C28—H28C	109.5
C9—C8—N2	125.1 (3)	H28B—C28—H28C	109.5
C13—C8—N2	117.0 (2)	N5—C29—H29A	109.5
C10—C9—C8	120.4 (3)	N5—C29—H29B	109.5
C10—C9—H9	119.8	H29A—C29—H29B	109.5
C8—C9—H9	119.8	N5—C29—H29C	109.5
C11—C10—C9	121.2 (3)	H29A—C29—H29C	109.5
C11—C10—H10	119.4	H29B—C29—H29C	109.5
C9—C10—H10	119.4	C30—N6—C31	114.9 (7)
C10—C11—C12	119.3 (3)	C30—N6—C32	139.8 (8)
C10—C11—H11	120.4	C31—N6—C32	105.2 (7)
C12—C11—H11	120.4	O5—C30—N6	120.3 (7)
C13—C12—C11	119.7 (3)	O5—C30—H30	119.8
C13—C12—H12	120.2	N6—C30—H30	119.8
C11—C12—H12	120.2	C30'—N6'—C32'	134.2 (8)
C12—C13—O2	123.9 (2)	C30'—N6'—C31'	125.3 (7)
C12—C13—C8	121.4 (3)	C32'—N6'—C31'	100.4 (7)
O2—C13—C8	114.7 (2)	O5'—C30'—N6'	127.0 (8)
C15—C14—O2	122.5 (3)	O5'—C30'—H30'	116.5
C15—C14—C19	121.3 (3)	N6'—C30'—H30'	116.5
O2—C14—C19	116.1 (2)	N6'—C31'—H31D	109.5
C14—C15—C16	119.6 (3)	N6'—C31'—H31E	109.5
C14—C15—H15	120.2	H31D—C31'—H31E	109.5
C16—C15—H15	120.2	N6'—C31'—H31F	109.5
C15—C16—C17	119.7 (3)	H31D—C31'—H31F	109.5
C15—C16—H16	120.1	H31E—C31'—H31F	109.5
C17—C16—H16	120.1	N6'—C32'—H32D	109.5
C16—C17—C18	121.0 (3)	N6'—C32'—H32E	109.5
C16—C17—H17	119.5	H32D—C32'—H32E	109.5
C18—C17—H17	119.5	N6'—C32'—H32F	109.5
C17—C18—C19	119.8 (3)	H32D—C32'—H32F	109.5
C17—C18—H18	120.1	H32E—C32'—H32F	109.5
C19—C18—H18	120.1
C6—C1—C2—C3	0.5 (6)	C19—C14—C15—C16	1.8 (5)
C1—C2—C3—C4	−0.5 (5)	C14—C15—C16—C17	−1.2 (5)
C2—C3—C4—C5	0.0 (5)	C15—C16—C17—C18	−0.1 (5)
C2—C3—C4—N1	−179.6 (3)	C16—C17—C18—C19	0.7 (5)
C7—N1—C4—C3	0.2 (5)	C17—C18—C19—C14	−0.1 (4)
C7—N1—C4—C5	−179.4 (3)	C17—C18—C19—N3	179.3 (3)
C3—C4—C5—C6	0.6 (5)	C15—C14—C19—C18	−1.1 (4)
N1—C4—C5—C6	−179.8 (3)	O2—C14—C19—C18	−176.3 (3)
C4—C5—C6—C1	−0.6 (6)	C15—C14—C19—N3	179.4 (3)
C2—C1—C6—C5	0.0 (6)	O2—C14—C19—N3	4.3 (4)
C4—N1—C7—O1	−4.1 (6)	C20—N3—C19—C18	20.4 (5)
C4—N1—C7—N2	176.4 (3)	C20—N3—C19—C14	−160.2 (3)
C8—N2—C7—O1	−3.1 (5)	C21—N4—C20—O3	−0.4 (6)
C8—N2—C7—N1	176.4 (3)	C21—N4—C20—N3	179.9 (3)
C7—N2—C8—C9	3.0 (5)	C19—N3—C20—O3	−1.3 (5)
C7—N2—C8—C13	−176.7 (3)	C19—N3—C20—N4	178.4 (3)
C13—C8—C9—C10	−0.2 (5)	C20—N4—C21—C22	−36.4 (5)
N2—C8—C9—C10	−179.9 (3)	C20—N4—C21—C26	144.9 (3)
C8—C9—C10—C11	0.0 (5)	C26—C21—C22—C23	−0.1 (5)
C9—C10—C11—C12	0.6 (5)	N4—C21—C22—C23	−178.8 (3)
C10—C11—C12—C13	−1.0 (5)	C21—C22—C23—C24	0.2 (5)
C11—C12—C13—O2	178.6 (3)	C22—C23—C24—C25	−0.2 (5)
C11—C12—C13—C8	0.8 (5)	C23—C24—C25—C26	0.2 (5)
C14—O2—C13—C12	15.8 (4)	C24—C25—C26—C21	−0.1 (5)
C14—O2—C13—C8	−166.3 (3)	C22—C21—C26—C25	0.0 (5)
C9—C8—C13—C12	−0.2 (4)	N4—C21—C26—C25	178.8 (3)
N2—C8—C13—C12	179.5 (3)	C29—N5—C27—O4	−176.1 (4)
C9—C8—C13—O2	−178.2 (3)	C28—N5—C27—O4	1.2 (6)
N2—C8—C13—O2	1.6 (4)	C31—N6—C30—O5	−2.7 (13)
C13—O2—C14—C15	54.7 (4)	C32—N6—C30—O5	−178.0 (11)
C13—O2—C14—C19	−130.2 (3)	C32'—N6'—C30'—O5'	−176.1 (11)
O2—C14—C15—C16	176.6 (3)	C31'—N6'—C30'—O5'	−0.2 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.88	1.99	2.847 (4)	163
N2—H2N···O4	0.88	2.17	2.977 (4)	153
N3—H3N···O5i	0.88	2.03	2.809 (8)	147
N3—H3N···O5'i	0.88	2.14	2.935 (7)	150
N4—H4N···O5'i	0.88	1.92	2.765 (8)	161
N4—H4N···O5i	0.88	2.40	3.101 (8)	137
C24—H24···O3ii	0.95	2.68	3.573 (5)	157
C32—H32B···O3iii	0.98	2.67	3.455 (11)	138
C31—H31A···Cg1	0.98	2.53	3.440 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.88	1.99	2.847 (4)	163
N2—H2N⋯O4	0.88	2.17	2.977 (4)	153
N3—H3N⋯O5i	0.88	2.03	2.809 (8)	147
N3—H3N⋯O5′i	0.88	2.14	2.935 (7)	150
N4—H4N⋯O5′i	0.88	1.92	2.765 (8)	161
N4—H4N⋯O5i	0.88	2.40	3.101 (8)	137
C24—H24⋯O3ii	0.95	2.68	3.573 (5)	157
C32—H32B⋯O3iii	0.98	2.67	3.455 (11)	138
C31—H31A⋯Cg1	0.98	2.53	3.440 (4)	154

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