1,1'-[o-Phenyl-enebis(nitrilo-methyl-idyne)]di-2-naphthol ethanol hemisolvate.

The asymmetric unit of the title compound, C(28)H(20)N(2)O(2)·0.5C(2)H(5)OH, contains two independent mol-ecules of 1,1'-[o-phenyl-enebis(nitrilo-methyl-idyne)]di-2-naphthol, denoted A and B, and one ethanol solvent mol-ecule. The hydr-oxy groups are involved in intra-molecular O-H⋯N hydrogen bonds influencing the mol-ecular conformations, which are slightly different in mol-ecules A and B, where the two bicyclic systems form dihedral angles of 51.93 (9) and 58.52 (9)°, respectively. In the crystal structure, a number of short inter-molecular C⋯C contacts with distances of less than 3.5 Å suggest the existence of π-π inter-actions, which contribute to the stability of the crystal packing.

Related literature

For related crystal structures, see: Zhang et al. (1990 ▶); Lo et al. (2006 ▶); Eltayeb et al. (2007 ▶).

Experimental

Crystal data

C28H20N2O2·0.5C2H6O

M = 439.50

Orthorhombic,

a = 19.956 (2) Å

b = 12.4742 (13) Å

c = 18.189 (2) Å

V = 4527.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.994

21755 measured reflections

4002 independent reflections

1545 reflections with I > 2σ(I)

R int = 0.176

Refinement

R[F 2 > 2σ(F 2)] = 0.094

wR(F 2) = 0.121

S = 1.05

4002 reflections

605 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021740/cv2421sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021740/cv2421Isup2.hkl

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

C28H20N2O2·0.5(C2H6O)	Dx = 1.289 Mg m−3
Mr = 439.50	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1646 reflections
a = 19.956 (2) Å	θ = 2.9–28.1º
b = 12.4742 (13) Å	µ = 0.08 mm−1
c = 18.189 (2) Å	T = 298 (2) K
V = 4527.9 (8) Å3	Block, yellow
Z = 8	0.20 × 0.18 × 0.07 mm
F000 = 1848

Bruker SMART CCD area-detector diffractometer	4002 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.176
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −19→23
Tmin = 0.984, Tmax = 0.994	k = −14→14
21755 measured reflections	l = −21→21

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)] = 0.094	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.026P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4002 reflections	Δρmax = 0.15 e Å−3
605 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
N1	0.4622 (4)	0.4463 (5)	0.2203 (4)	0.061 (2)
N2	0.5628 (4)	0.3113 (6)	0.1967 (4)	0.065 (2)
N3	0.2294 (4)	0.5681 (6)	0.1085 (4)	0.061 (2)
N4	0.1288 (4)	0.7009 (6)	0.1347 (5)	0.069 (2)
O1	0.5069 (4)	0.5421 (5)	0.1076 (4)	0.087 (2)
H1	0.5021	0.4946	0.1383	0.130*
O2	0.6557 (3)	0.4250 (5)	0.1367 (4)	0.088 (2)
H2	0.6266	0.4091	0.1666	0.132*
O3	0.1832 (4)	0.4657 (5)	0.2186 (4)	0.090 (2)
H3	0.1863	0.5130	0.1876	0.136*
O4	0.0335 (4)	0.5789 (5)	0.1839 (4)	0.090 (3)
H4	0.0640	0.5976	0.1565	0.136*
O5	0.1992 (5)	0.5525 (9)	0.3589 (5)	0.175 (5)
H5	0.1973	0.5175	0.3208	0.263*
C1	0.4667 (5)	0.3606 (7)	0.2677 (5)	0.058 (3)
C2	0.5175 (6)	0.2856 (7)	0.2548 (5)	0.065 (3)
C3	0.5266 (6)	0.1963 (8)	0.2979 (6)	0.081 (3)
H3A	0.5622	0.1499	0.2890	0.097*
C4	0.4820 (6)	0.1766 (8)	0.3547 (6)	0.083 (3)
H4A	0.4862	0.1145	0.3826	0.100*
C5	0.4317 (6)	0.2479 (8)	0.3701 (6)	0.085 (4)
H5A	0.4033	0.2357	0.4098	0.102*
C6	0.4232 (6)	0.3379 (8)	0.3269 (5)	0.075 (3)
H6	0.3881	0.3845	0.3370	0.090*
C7	0.4192 (5)	0.5246 (7)	0.2259 (5)	0.058 (3)
H7	0.3892	0.5234	0.2650	0.070*
C8	0.4156 (6)	0.6088 (8)	0.1773 (6)	0.061 (3)
C9	0.4628 (6)	0.6155 (8)	0.1181 (7)	0.069 (3)
C10	0.4633 (6)	0.7026 (9)	0.0693 (6)	0.081 (3)
H10	0.4929	0.7036	0.0299	0.097*
C11	0.4208 (7)	0.7840 (9)	0.0800 (7)	0.085 (4)
H11	0.4235	0.8436	0.0493	0.102*
C12	0.3710 (6)	0.7826 (8)	0.1374 (6)	0.070 (3)
C13	0.3675 (5)	0.6957 (8)	0.1864 (6)	0.059 (3)
C14	0.3169 (6)	0.6970 (9)	0.2400 (5)	0.067 (3)
H14	0.3126	0.6395	0.2723	0.081*
C15	0.2741 (6)	0.7811 (9)	0.2454 (6)	0.082 (4)
H15	0.2405	0.7791	0.2809	0.099*
C16	0.2785 (6)	0.8696 (9)	0.2000 (7)	0.087 (4)
H16	0.2497	0.9277	0.2056	0.104*
C17	0.3271 (6)	0.8687 (9)	0.1464 (6)	0.082 (4)
H17	0.3308	0.9274	0.1151	0.098*
C18	0.5801 (5)	0.2358 (8)	0.1518 (5)	0.057 (3)
H18	0.5614	0.1680	0.1578	0.069*
C19	0.6269 (5)	0.2526 (7)	0.0933 (5)	0.053 (3)
C20	0.6634 (6)	0.3443 (8)	0.0881 (6)	0.070 (3)
C21	0.7127 (6)	0.3604 (10)	0.0342 (7)	0.090 (4)
H21	0.7369	0.4242	0.0329	0.108*
C22	0.7249 (7)	0.2819 (12)	−0.0164 (7)	0.097 (4)
H22	0.7582	0.2917	−0.0516	0.116*
C23	0.6875 (6)	0.1859 (11)	−0.0156 (6)	0.079 (3)
C24	0.6383 (6)	0.1729 (8)	0.0383 (6)	0.064 (3)
C25	0.6016 (6)	0.0770 (9)	0.0364 (5)	0.077 (3)
H25	0.5687	0.0650	0.0717	0.093*
C26	0.6131 (7)	0.0004 (9)	−0.0165 (7)	0.091 (4)
H26	0.5871	−0.0615	−0.0167	0.109*
C27	0.6626 (8)	0.0126 (11)	−0.0696 (7)	0.112 (5)
H27	0.6701	−0.0399	−0.1050	0.134*
C28	0.6992 (8)	0.1034 (12)	−0.0680 (6)	0.104 (5)
H28	0.7333	0.1124	−0.1022	0.125*
C29	0.2245 (6)	0.6585 (8)	0.0626 (5)	0.061 (3)
C30	0.1732 (6)	0.7312 (8)	0.0783 (6)	0.061 (3)
C31	0.1655 (6)	0.8246 (8)	0.0391 (5)	0.073 (3)
H31	0.1312	0.8723	0.0503	0.087*
C32	0.2102 (7)	0.8460 (9)	−0.0176 (7)	0.092 (4)
H32	0.2059	0.9091	−0.0445	0.111*
C33	0.2607 (8)	0.7748 (11)	−0.0346 (6)	0.099 (5)
H33	0.2894	0.7896	−0.0735	0.119*
C34	0.2692 (6)	0.6825 (10)	0.0052 (6)	0.084 (4)
H34	0.3043	0.6361	−0.0057	0.101*
C35	0.2738 (6)	0.4901 (9)	0.1006 (5)	0.070 (3)
H35	0.3048	0.4940	0.0625	0.085*
C36	0.2755 (5)	0.4010 (10)	0.1486 (6)	0.065 (3)
C37	0.2286 (6)	0.3932 (9)	0.2067 (6)	0.070 (3)
C38	0.2295 (7)	0.3021 (11)	0.2539 (6)	0.095 (4)
H38	0.1984	0.2963	0.2918	0.114*
C39	0.2755 (7)	0.2246 (10)	0.2437 (7)	0.096 (4)
H39	0.2760	0.1669	0.2760	0.115*
C40	0.3226 (6)	0.2265 (11)	0.1868 (7)	0.082 (3)
C41	0.3239 (6)	0.3154 (10)	0.1385 (6)	0.070 (3)
C42	0.3731 (7)	0.3146 (9)	0.0840 (7)	0.090 (4)
H42	0.3755	0.3720	0.0515	0.107*
C43	0.4186 (6)	0.2309 (11)	0.0766 (9)	0.108 (5)
H43	0.4513	0.2328	0.0403	0.130*
C44	0.4144 (7)	0.1455 (12)	0.1239 (9)	0.110 (5)
H44	0.4440	0.0884	0.1188	0.132*
C45	0.3684 (7)	0.1434 (11)	0.1771 (8)	0.100 (5)
H45	0.3668	0.0848	0.2087	0.120*
C46	0.1101 (5)	0.7724 (7)	0.1818 (5)	0.062 (3)
H46	0.1284	0.8409	0.1790	0.074*
C47	0.0611 (6)	0.7490 (8)	0.2394 (5)	0.066 (3)
C48	0.0233 (6)	0.6535 (10)	0.2340 (6)	0.072 (3)
C49	−0.0279 (6)	0.6367 (9)	0.2871 (8)	0.089 (4)
H49	−0.0544	0.5755	0.2842	0.107*
C50	−0.0385 (7)	0.7058 (12)	0.3396 (6)	0.104 (5)
H50	−0.0734	0.6908	0.3718	0.124*
C51	−0.0030 (8)	0.7987 (10)	0.3522 (7)	0.095 (4)
C52	0.0501 (6)	0.8240 (9)	0.2981 (6)	0.076 (3)
C53	0.0881 (6)	0.9171 (10)	0.3089 (6)	0.084 (4)
H53	0.1216	0.9349	0.2755	0.101*
C54	0.0765 (8)	0.9826 (9)	0.3685 (8)	0.132 (6)
H54	0.1031	1.0429	0.3757	0.159*
C55	0.0237 (10)	0.9590 (13)	0.4198 (7)	0.134 (7)
H55	0.0144	1.0041	0.4592	0.161*
C56	−0.0111 (9)	0.8695 (13)	0.4085 (8)	0.124 (6)
H56	−0.0445	0.8538	0.4425	0.148*
C57	0.1328 (10)	0.5731 (16)	0.3850 (11)	0.188 (8)
H57A	0.1299	0.6484	0.3977	0.226*
H57B	0.1020	0.5608	0.3446	0.226*
C58	0.1125 (10)	0.5189 (14)	0.4398 (11)	0.220 (9)
H58A	0.1198	0.4440	0.4307	0.329*
H58B	0.0656	0.5317	0.4473	0.329*
H58C	0.1369	0.5402	0.4830	0.329*

	U11	U22	U33	U12	U13	U23
N1	0.086 (7)	0.021 (4)	0.074 (5)	0.002 (4)	−0.003 (5)	0.004 (4)
N2	0.056 (6)	0.066 (5)	0.073 (6)	0.002 (5)	0.004 (5)	−0.008 (5)
N3	0.061 (6)	0.059 (5)	0.062 (5)	−0.004 (5)	−0.003 (5)	−0.008 (5)
N4	0.069 (7)	0.068 (5)	0.070 (6)	−0.007 (5)	0.004 (6)	0.000 (5)
O1	0.095 (6)	0.086 (5)	0.079 (5)	0.006 (5)	0.019 (5)	0.007 (4)
O2	0.068 (6)	0.073 (4)	0.123 (6)	−0.013 (4)	0.019 (5)	0.005 (5)
O3	0.087 (6)	0.113 (5)	0.070 (5)	0.013 (5)	0.007 (5)	0.010 (4)
O4	0.095 (7)	0.083 (5)	0.093 (5)	−0.020 (5)	0.004 (5)	−0.003 (5)
O5	0.127 (9)	0.277 (13)	0.122 (8)	−0.038 (10)	0.012 (8)	−0.059 (8)
C1	0.059 (8)	0.043 (6)	0.073 (7)	−0.003 (6)	0.007 (6)	−0.020 (6)
C2	0.079 (9)	0.050 (6)	0.065 (7)	−0.017 (6)	0.007 (7)	0.007 (6)
C3	0.072 (9)	0.075 (8)	0.096 (9)	0.012 (7)	0.012 (8)	0.010 (7)
C4	0.081 (9)	0.088 (8)	0.081 (8)	0.011 (7)	0.016 (7)	0.030 (7)
C5	0.093 (10)	0.093 (9)	0.070 (8)	0.011 (7)	0.036 (7)	0.013 (7)
C6	0.085 (9)	0.078 (8)	0.063 (7)	0.011 (7)	0.013 (7)	−0.002 (6)
C7	0.076 (8)	0.041 (5)	0.058 (6)	−0.012 (6)	0.000 (6)	−0.004 (5)
C8	0.066 (9)	0.057 (7)	0.060 (7)	−0.013 (6)	0.002 (7)	−0.009 (6)
C9	0.074 (10)	0.057 (7)	0.077 (8)	0.003 (7)	−0.016 (8)	−0.014 (7)
C10	0.083 (11)	0.081 (8)	0.077 (8)	0.000 (8)	0.004 (7)	0.002 (7)
C11	0.094 (11)	0.086 (9)	0.075 (9)	−0.015 (8)	−0.007 (8)	0.013 (7)
C12	0.064 (9)	0.073 (7)	0.072 (8)	−0.001 (7)	−0.022 (7)	−0.011 (7)
C13	0.065 (8)	0.057 (6)	0.054 (6)	−0.007 (6)	−0.022 (7)	−0.004 (6)
C14	0.061 (8)	0.076 (7)	0.066 (7)	0.001 (7)	−0.006 (7)	−0.015 (6)
C15	0.068 (10)	0.084 (8)	0.094 (9)	−0.001 (8)	−0.013 (7)	−0.025 (8)
C16	0.080 (10)	0.070 (8)	0.110 (10)	0.011 (7)	−0.021 (9)	−0.020 (8)
C17	0.079 (10)	0.083 (8)	0.082 (9)	−0.001 (8)	−0.014 (8)	0.007 (7)
C18	0.047 (7)	0.062 (6)	0.062 (7)	−0.007 (6)	−0.002 (6)	0.021 (6)
C19	0.062 (8)	0.032 (5)	0.066 (7)	0.014 (5)	0.005 (6)	0.007 (5)
C20	0.074 (9)	0.044 (6)	0.091 (8)	0.009 (6)	0.008 (7)	0.006 (6)
C21	0.075 (10)	0.088 (9)	0.107 (10)	−0.007 (8)	0.024 (8)	0.031 (8)
C22	0.090 (11)	0.109 (11)	0.091 (10)	0.010 (9)	0.019 (9)	0.037 (8)
C23	0.075 (9)	0.109 (10)	0.053 (7)	0.023 (8)	0.016 (7)	0.028 (7)
C24	0.064 (8)	0.050 (6)	0.077 (8)	0.008 (6)	−0.009 (7)	0.021 (6)
C25	0.098 (10)	0.083 (8)	0.050 (6)	0.041 (7)	−0.010 (6)	−0.004 (6)
C26	0.104 (11)	0.094 (9)	0.074 (8)	0.008 (8)	−0.025 (8)	0.000 (8)
C27	0.153 (17)	0.113 (11)	0.069 (9)	0.035 (11)	−0.011 (10)	−0.013 (9)
C28	0.129 (14)	0.130 (11)	0.052 (7)	0.044 (11)	0.015 (8)	0.001 (9)
C29	0.076 (9)	0.058 (6)	0.050 (6)	−0.009 (6)	−0.011 (6)	−0.013 (6)
C30	0.070 (9)	0.058 (7)	0.053 (7)	−0.009 (6)	−0.004 (6)	−0.009 (6)
C31	0.091 (10)	0.074 (7)	0.053 (6)	−0.015 (6)	0.002 (7)	0.009 (6)
C32	0.125 (12)	0.080 (9)	0.072 (8)	−0.024 (9)	−0.020 (9)	−0.005 (7)
C33	0.135 (15)	0.099 (10)	0.064 (8)	−0.042 (10)	0.003 (8)	0.001 (8)
C34	0.083 (10)	0.105 (10)	0.065 (7)	−0.024 (8)	0.021 (7)	−0.012 (7)
C35	0.070 (9)	0.085 (7)	0.057 (7)	−0.018 (7)	0.004 (6)	−0.021 (6)
C36	0.030 (7)	0.098 (9)	0.066 (8)	−0.002 (7)	0.003 (6)	−0.013 (7)
C37	0.046 (8)	0.098 (9)	0.067 (8)	0.006 (7)	−0.015 (7)	−0.005 (7)
C38	0.096 (12)	0.126 (10)	0.062 (8)	0.000 (9)	−0.013 (8)	0.029 (8)
C39	0.087 (11)	0.108 (10)	0.091 (10)	0.000 (9)	−0.020 (9)	0.019 (8)
C40	0.067 (10)	0.093 (9)	0.085 (9)	0.000 (8)	−0.007 (8)	−0.011 (8)
C41	0.045 (8)	0.095 (9)	0.069 (8)	−0.009 (7)	0.002 (7)	−0.012 (7)
C42	0.085 (10)	0.079 (8)	0.105 (10)	−0.007 (8)	−0.005 (9)	−0.013 (7)
C43	0.068 (11)	0.093 (10)	0.163 (13)	0.009 (9)	0.000 (9)	−0.017 (10)
C44	0.072 (12)	0.096 (11)	0.161 (15)	0.010 (9)	−0.014 (11)	−0.032 (11)
C45	0.081 (12)	0.089 (9)	0.130 (14)	−0.009 (9)	−0.014 (10)	−0.006 (9)
C46	0.061 (8)	0.062 (6)	0.063 (7)	−0.005 (6)	−0.010 (6)	0.012 (6)
C47	0.061 (8)	0.076 (7)	0.060 (7)	0.005 (7)	−0.009 (6)	0.012 (6)
C48	0.060 (9)	0.093 (9)	0.063 (7)	0.002 (8)	−0.002 (7)	0.031 (7)
C49	0.064 (9)	0.098 (9)	0.105 (10)	0.006 (7)	−0.008 (9)	0.028 (8)
C50	0.118 (13)	0.123 (12)	0.070 (9)	0.050 (11)	0.026 (9)	0.015 (9)
C51	0.138 (14)	0.078 (10)	0.070 (9)	0.051 (9)	−0.003 (10)	0.004 (8)
C52	0.087 (10)	0.084 (9)	0.056 (7)	0.026 (8)	0.000 (7)	0.013 (7)
C53	0.098 (11)	0.085 (8)	0.069 (8)	0.028 (8)	−0.012 (7)	−0.007 (7)
C54	0.198 (18)	0.112 (11)	0.087 (9)	0.065 (11)	−0.040 (11)	−0.025 (9)
C55	0.21 (2)	0.130 (13)	0.060 (9)	0.080 (14)	0.012 (11)	−0.013 (10)
C56	0.176 (18)	0.116 (11)	0.078 (10)	0.077 (12)	0.017 (10)	0.023 (10)
C57	0.17 (2)	0.26 (2)	0.134 (17)	0.003 (19)	−0.054 (16)	0.041 (15)
C58	0.24 (2)	0.26 (2)	0.157 (17)	−0.066 (17)	−0.024 (17)	0.073 (14)

N1—C7	1.304 (9)	C25—H25	0.9300
N1—C1	1.376 (10)	C26—C27	1.389 (16)
N2—C18	1.294 (10)	C26—H26	0.9300
N2—C2	1.426 (10)	C27—C28	1.349 (15)
N3—C35	1.324 (11)	C27—H27	0.9300
N3—C29	1.406 (10)	C28—H28	0.9300
N4—C46	1.292 (10)	C29—C30	1.398 (12)
N4—C30	1.408 (11)	C29—C34	1.405 (13)
O1—C9	1.284 (11)	C30—C31	1.374 (12)
O1—H1	0.8200	C31—C32	1.389 (14)
O2—C20	1.348 (10)	C31—H31	0.9300
O2—H2	0.8200	C32—C33	1.378 (14)
O3—C37	1.299 (10)	C32—H32	0.9300
O3—H3	0.8200	C33—C34	1.370 (14)
O4—C48	1.319 (12)	C33—H33	0.9300
O4—H4	0.8200	C34—H34	0.9300
O5—C57	1.43 (2)	C35—C36	1.414 (13)
O5—H5	0.8200	C35—H35	0.9300
C1—C2	1.400 (12)	C36—C37	1.415 (13)
C1—C6	1.411 (12)	C36—C41	1.452 (14)
C2—C3	1.374 (12)	C37—C38	1.424 (12)
C3—C4	1.387 (13)	C38—C39	1.347 (14)
C3—H3A	0.9300	C38—H38	0.9300
C4—C5	1.369 (12)	C39—C40	1.397 (14)
C4—H4A	0.9300	C39—H39	0.9300
C5—C6	1.381 (12)	C40—C45	1.392 (15)
C5—H5A	0.9300	C40—C41	1.415 (14)
C6—H6	0.9300	C41—C42	1.394 (13)
C7—C8	1.374 (12)	C42—C43	1.390 (14)
C7—H7	0.9300	C42—H42	0.9300
C8—C9	1.434 (14)	C43—C44	1.371 (16)
C8—C13	1.456 (13)	C43—H43	0.9300
C9—C10	1.402 (13)	C44—C45	1.335 (16)
C10—C11	1.337 (14)	C44—H44	0.9300
C10—H10	0.9300	C45—H45	0.9300
C11—C12	1.442 (14)	C46—C47	1.463 (12)
C11—H11	0.9300	C46—H46	0.9300
C12—C17	1.396 (13)	C47—C48	1.413 (13)
C12—C13	1.405 (12)	C47—C52	1.436 (13)
C13—C14	1.405 (12)	C48—C49	1.421 (14)
C14—C15	1.357 (12)	C49—C50	1.304 (13)
C14—H14	0.9300	C49—H49	0.9300
C15—C16	1.381 (12)	C50—C51	1.377 (16)
C15—H15	0.9300	C50—H50	0.9300
C16—C17	1.377 (14)	C51—C56	1.361 (14)
C16—H16	0.9300	C51—C52	1.480 (16)
C17—H17	0.9300	C52—C53	1.401 (14)
C18—C19	1.432 (12)	C53—C54	1.377 (15)
C18—H18	0.9300	C53—H53	0.9300
C19—C20	1.359 (12)	C54—C55	1.437 (18)
C19—C24	1.428 (12)	C54—H54	0.9300
C20—C21	1.404 (13)	C55—C56	1.332 (19)
C21—C22	1.366 (14)	C55—H55	0.9300
C21—H21	0.9300	C56—H56	0.9300
C22—C23	1.411 (14)	C57—C58	1.271 (18)
C22—H22	0.9300	C57—H57A	0.9700
C23—C24	1.398 (13)	C57—H57B	0.9700
C23—C28	1.421 (15)	C58—H58A	0.9600
C24—C25	1.403 (13)	C58—H58B	0.9600
C25—C26	1.377 (13)	C58—H58C	0.9600
C8···C35	3.485 (16)	C9···C47i	3.402 (16)
C12···C34	3.387 (16)	C13···C49i	3.475 (16)
C15···C46	3.473 (15)	C19···C37ii	3.418 (15)
C1···C54i	3.462 (17)	C26···C29ii	3.308 (17)
C7···C52i	3.481 (15)
C7—N1—C1	125.2 (9)	C34—C29—N3	124.6 (11)
C18—N2—C2	118.2 (8)	C31—C30—C29	121.7 (11)
C35—N3—C29	124.9 (10)	C31—C30—N4	122.4 (11)
C46—N4—C30	118.6 (9)	C29—C30—N4	115.8 (9)
C9—O1—H1	109.5	C30—C31—C32	118.5 (11)
C20—O2—H2	109.5	C30—C31—H31	120.8
C37—O3—H3	109.5	C32—C31—H31	120.8
C48—O4—H4	109.5	C33—C32—C31	120.7 (12)
C57—O5—H5	109.5	C33—C32—H32	119.6
N1—C1—C2	117.5 (10)	C31—C32—H32	119.6
N1—C1—C6	126.4 (10)	C34—C33—C32	121.0 (13)
C2—C1—C6	116.1 (9)	C34—C33—H33	119.5
C3—C2—C1	122.8 (11)	C32—C33—H33	119.5
C3—C2—N2	121.4 (11)	C33—C34—C29	119.5 (12)
C1—C2—N2	115.6 (9)	C33—C34—H34	120.3
C2—C3—C4	118.9 (11)	C29—C34—H34	120.3
C2—C3—H3A	120.5	N3—C35—C36	121.8 (10)
C4—C3—H3A	120.5	N3—C35—H35	119.1
C5—C4—C3	120.6 (10)	C36—C35—H35	119.1
C5—C4—H4A	119.7	C35—C36—C37	120.0 (11)
C3—C4—H4A	119.7	C35—C36—C41	121.0 (11)
C4—C5—C6	120.1 (10)	C37—C36—C41	118.9 (11)
C4—C5—H5A	120.0	O3—C37—C36	122.6 (11)
C6—C5—H5A	120.0	O3—C37—C38	117.6 (12)
C5—C6—C1	121.5 (10)	C36—C37—C38	119.8 (12)
C5—C6—H6	119.3	C39—C38—C37	119.9 (13)
C1—C6—H6	119.3	C39—C38—H38	120.0
N1—C7—C8	123.9 (10)	C37—C38—H38	120.0
N1—C7—H7	118.0	C38—C39—C40	123.3 (13)
C8—C7—H7	118.0	C38—C39—H39	118.4
C7—C8—C9	119.5 (11)	C40—C39—H39	118.4
C7—C8—C13	122.1 (11)	C45—C40—C39	121.4 (15)
C9—C8—C13	118.3 (10)	C45—C40—C41	119.5 (13)
O1—C9—C10	116.9 (12)	C39—C40—C41	119.0 (13)
O1—C9—C8	121.4 (11)	C42—C41—C40	116.6 (12)
C10—C9—C8	121.7 (11)	C42—C41—C36	124.3 (12)
C11—C10—C9	119.5 (12)	C40—C41—C36	119.1 (12)
C11—C10—H10	120.3	C43—C42—C41	122.3 (13)
C9—C10—H10	120.3	C43—C42—H42	118.9
C10—C11—C12	122.2 (11)	C41—C42—H42	118.9
C10—C11—H11	118.9	C44—C43—C42	118.9 (14)
C12—C11—H11	118.9	C44—C43—H43	120.6
C17—C12—C13	119.3 (12)	C42—C43—H43	120.6
C17—C12—C11	120.5 (12)	C45—C44—C43	120.8 (16)
C13—C12—C11	120.2 (11)	C45—C44—H44	119.6
C12—C13—C14	117.8 (11)	C43—C44—H44	119.6
C12—C13—C8	118.1 (11)	C44—C45—C40	121.9 (15)
C14—C13—C8	124.1 (10)	C44—C45—H45	119.0
C15—C14—C13	120.8 (11)	C40—C45—H45	119.0
C15—C14—H14	119.6	N4—C46—C47	122.0 (9)
C13—C14—H14	119.6	N4—C46—H46	119.0
C14—C15—C16	122.3 (12)	C47—C46—H46	119.0
C14—C15—H15	118.8	C48—C47—C52	121.3 (11)
C16—C15—H15	118.8	C48—C47—C46	118.4 (10)
C17—C16—C15	117.5 (12)	C52—C47—C46	120.3 (11)
C17—C16—H16	121.2	O4—C48—C47	124.1 (11)
C15—C16—H16	121.2	O4—C48—C49	118.5 (12)
C16—C17—C12	122.1 (12)	C47—C48—C49	117.4 (12)
C16—C17—H17	118.9	C50—C49—C48	121.1 (13)
C12—C17—H17	118.9	C50—C49—H49	119.4
N2—C18—C19	122.5 (9)	C48—C49—H49	119.4
N2—C18—H18	118.8	C49—C50—C51	126.5 (14)
C19—C18—H18	118.8	C49—C50—H50	116.7
C20—C19—C24	116.9 (10)	C51—C50—H50	116.7
C20—C19—C18	121.6 (10)	C56—C51—C50	127.6 (17)
C24—C19—C18	121.5 (9)	C56—C51—C52	116.5 (14)
O2—C20—C19	121.5 (10)	C50—C51—C52	115.9 (12)
O2—C20—C21	115.5 (11)	C53—C52—C47	124.2 (12)
C19—C20—C21	123.0 (11)	C53—C52—C51	118.1 (12)
C22—C21—C20	119.5 (12)	C47—C52—C51	117.7 (12)
C22—C21—H21	120.2	C54—C53—C52	120.7 (13)
C20—C21—H21	120.2	C54—C53—H53	119.6
C21—C22—C23	120.5 (13)	C52—C53—H53	119.6
C21—C22—H22	119.8	C53—C54—C55	120.9 (14)
C23—C22—H22	119.8	C53—C54—H54	119.6
C24—C23—C22	118.5 (12)	C55—C54—H54	119.6
C24—C23—C28	120.1 (13)	C56—C55—C54	117.0 (14)
C22—C23—C28	121.4 (13)	C56—C55—H55	121.5
C23—C24—C25	116.6 (11)	C54—C55—H55	121.5
C23—C24—C19	121.5 (11)	C55—C56—C51	126.8 (17)
C25—C24—C19	121.9 (10)	C55—C56—H56	116.6
C26—C25—C24	121.5 (12)	C51—C56—H56	116.6
C26—C25—H25	119.3	C58—C57—O5	117.4 (19)
C24—C25—H25	119.3	C58—C57—H57A	108.0
C25—C26—C27	122.0 (13)	O5—C57—H57A	108.0
C25—C26—H26	119.0	C58—C57—H57B	108.0
C27—C26—H26	119.0	O5—C57—H57B	108.0
C28—C27—C26	117.5 (14)	H57A—C57—H57B	107.2
C28—C27—H27	121.3	C57—C58—H58A	109.5
C26—C27—H27	121.3	C57—C58—H58B	109.5
C27—C28—C23	122.3 (14)	H58A—C58—H58B	109.5
C27—C28—H28	118.9	C57—C58—H58C	109.5
C23—C28—H28	118.9	H58A—C58—H58C	109.5
C30—C29—C34	118.6 (10)	H58B—C58—H58C	109.5
C30—C29—N3	116.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3	0.82	1.99	2.790 (11)	166
O4—H4···N4	0.82	1.87	2.594 (11)	147
O3—H3···N3	0.82	1.81	2.550 (10)	149
O2—H2···N2	0.82	1.85	2.578 (10)	148
O1—H1···N1	0.82	1.79	2.535 (9)	149

Table 1

Selected interatomic distances (Å)

C8⋯C35	3.485 (16)
C12⋯C34	3.387 (16)
C15⋯C46	3.473 (15)
C1⋯C54i	3.462 (17)
C7⋯C52i	3.481 (15)
C9⋯C47i	3.402 (16)
C13⋯C49i	3.475 (16)
C19⋯C37ii	3.418 (15)
C26⋯C29ii	3.308 (17)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O3	0.82	1.99	2.790 (11)	166
O4—H4⋯N4	0.82	1.87	2.594 (11)	147
O3—H3⋯N3	0.82	1.81	2.550 (10)	149
O2—H2⋯N2	0.82	1.85	2.578 (10)	148
O1—H1⋯N1	0.82	1.79	2.535 (9)	149