N,N-Di-phenyl-4-(1H-pyrrolo[1,2-f][1,10]phenanthro-lin-2-yl)-aniline ethanol monosolvate.

The title compound, C32H21N4·C2H5OH, crystallized as an ethanol monosolvate. In the mol-ecule of this phenanthroline derivative, the pyridine rings are almost coplanar, making a dihedral angle of 1.54 (13)°. The tri-phenyl-amine group, introduced as an electron donor, shows a propeller-type structure, and the dihedral angles between the benzene rings are 68.71 11), 63.92 (16) and 70.81 (15)°. In the crystal, the phenanthroline mol-ecules are linked via the solvent mol-ecule by N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds, leading to the formation of zigzag chains propagating along [010]. These chains are linked via C-H⋯N hydrogen bonds, forming undulating two-dimensional networks extending in the a- and b-axis directions.

Related literature

For background to imidazo[4,5-f]-1,10-phenanthroline compounds, see: Li et al. (2012 ▶). For metal complexes and binding studies, see: Ma et al. (2009 ▶); Xu et al. (2012 ▶); Zheng et al. (2013 ▶). For the crystal structures of related compounds, see: Sun et al. (2009 ▶); Eseola et al. (2012 ▶); Bhat et al. (2011 ▶).

Experimental

Crystal data

C32H21N4·C2H6O

M = 507.60

Monoclinic,

a = 9.716 (4) Å

b = 10.690 (4) Å

c = 27.017 (10) Å

β = 92.317 (4)°

V = 2803.8 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.985, T max = 0.993

20210 measured reflections

5216 independent reflections

3870 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.210

S = 1.02

5216 reflections

340 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008477/su2573sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008477/su2573Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008477/su2573Isup3.cml

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

C32H21N4·C2H6O	F(000) = 1068
Mr = 507.60	Dx = 1.202 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6506 reflections
a = 9.716 (4) Å	θ = 2.4–25.0°
b = 10.690 (4) Å	µ = 0.07 mm−1
c = 27.017 (10) Å	T = 296 K
β = 92.317 (4)°	Block, yellow
V = 2803.8 (18) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	5216 independent reflections
Radiation source: fine-focus sealed tube	3870 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.985, Tmax = 0.993	k = −12→12
20210 measured reflections	l = −32→32

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1148P)2 + 1.3126P] where P = (Fo2 + 2Fc2)/3
5216 reflections	(Δ/σ)max = 0.020
340 parameters	Δρmax = 0.51 e Å−3
6 restraints	Δρmin = −0.50 e Å−3

Experimental. Spectroscopic details for the title compound: 1H NMR (400 MHz, DMSO-d6) δ (p.p.m.): 7.12–7.15 (m, 8H), 7.38 (t, J=8.0 Hz, 4H), 7.82 (q, J=4.2 Hz, 2H), 8.17 (d, J=4.0 Hz, 2H), 8.89–8.92 (m, 2H), 9.01–9.02 (m, 2H). 13C NMR (150 MHz, DMSO-d6) δ (p.p.m.) 151.0, 148.2, 147.4, 146.7, 143.4, 129.7, 129.5, 127.5, 124.6, 123.9, 123.7, 123.1, 122.05. IR (KBr, cm-1): 3422(m), 3030(s), 1607(versus), 1485(versus), 1331(s), 1286(s), 1137(w), 739(s), 700(s). MS: m/z (%)= 464.12(M+, 100%).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.4844 (2)	−0.1863 (2)	0.29749 (8)	0.0636 (8)
N2	0.2262 (2)	−0.28229 (19)	0.29875 (7)	0.0536 (7)
N3	0.3274 (2)	0.04565 (18)	0.14710 (7)	0.0474 (6)
N4	0.0133 (2)	0.3171 (2)	−0.04486 (8)	0.0693 (8)
C1	0.6091 (3)	−0.1386 (3)	0.29806 (11)	0.0795 (11)
C2	0.6544 (3)	−0.0539 (3)	0.26334 (12)	0.0786 (11)
C3	0.5652 (3)	−0.0170 (3)	0.22597 (9)	0.0607 (8)
C4	0.4309 (2)	−0.0651 (2)	0.22369 (8)	0.0473 (7)
C5	0.3260 (2)	−0.0335 (2)	0.18724 (8)	0.0442 (7)
C6	0.1942 (2)	−0.0808 (2)	0.18772 (8)	0.0447 (7)
C7	0.1549 (2)	−0.1673 (2)	0.22489 (8)	0.0454 (7)
C8	0.2546 (2)	−0.2019 (2)	0.26137 (8)	0.0450 (7)
C9	0.3942 (2)	−0.1511 (2)	0.26082 (8)	0.0471 (7)
C10	0.0223 (3)	−0.2189 (3)	0.22706 (10)	0.0622 (9)
C11	−0.0038 (3)	−0.3001 (3)	0.26445 (11)	0.0718 (10)
C12	0.1002 (3)	−0.3279 (3)	0.29922 (10)	0.0629 (9)
C13	0.11393 (19)	−0.03287 (18)	0.14906 (7)	0.0347 (6)
C14	0.1974 (2)	0.0425 (2)	0.12546 (8)	0.0469 (7)
C15	0.1551 (2)	0.1150 (2)	0.08140 (8)	0.0466 (7)
C16	0.2373 (3)	0.2055 (3)	0.06061 (10)	0.0627 (9)
C17	0.1902 (3)	0.2714 (3)	0.01937 (10)	0.0687 (10)
C18	0.0619 (3)	0.2493 (2)	−0.00245 (9)	0.0568 (8)
C19	−0.0198 (3)	0.1581 (2)	0.01814 (9)	0.0568 (8)
C20	0.0266 (2)	0.0926 (2)	0.05941 (9)	0.0554 (8)
C21	0.10408 (15)	0.33915 (15)	−0.08378 (4)	0.0739 (11)
C22	0.19694 (16)	0.24825 (19)	−0.09791 (7)	0.0840 (13)
C23	0.28428 (16)	0.2720 (3)	−0.13631 (8)	0.1121 (16)
C24	0.2788 (2)	0.3867 (3)	−0.16057 (7)	0.1252 (12)
C25	0.1859 (2)	0.4776 (2)	−0.14644 (8)	0.152 (3)
C26	0.0986 (2)	0.45382 (15)	−0.10804 (7)	0.1127 (18)
C27	−0.12987 (17)	0.34159 (19)	−0.05179 (6)	0.0672 (10)
C28	−0.19577 (14)	0.3242 (2)	−0.09755 (8)	0.0911 (14)
C29	−0.3348 (5)	0.3488 (5)	−0.10367 (17)	0.1232 (19)
C30	−0.4097 (5)	0.3866 (5)	−0.0651 (2)	0.132 (2)
C31	−0.3455 (4)	0.4019 (4)	−0.01915 (16)	0.1133 (17)
C32	−0.2059 (4)	0.3818 (3)	−0.01277 (12)	0.0864 (12)
O1	0.55771 (19)	0.1730 (2)	0.11618 (7)	0.0698 (7)
C33	0.6124 (4)	0.0588 (5)	0.04600 (15)	0.1228 (19)
C34	0.6648 (4)	0.1264 (5)	0.08975 (13)	0.1040 (16)
H1	0.67110	−0.16310	0.32340	0.0950*
H2	0.74390	−0.02300	0.26550	0.0940*
H3	0.59310	0.03960	0.20220	0.0730*
H3N	0.404 (3)	0.087 (3)	0.1347 (10)	0.069 (8)*
H10	−0.04630	−0.19810	0.20350	0.0750*
H11	−0.09040	−0.33630	0.26660	0.0860*
H12	0.07980	−0.38260	0.32470	0.0760*
H16	0.32460	0.22180	0.07450	0.0750*
H17	0.24640	0.33210	0.00600	0.0820*
H19	−0.10660	0.14110	0.00400	0.0680*
H20	−0.02980	0.03200	0.07280	0.0660*
H22	0.20060	0.17150	−0.08170	0.1010*
H23	0.34640	0.21120	−0.14580	0.1340*
H24	0.33720	0.40260	−0.18630	0.1500*
H25	0.18220	0.55430	−0.16270	0.1830*
H26	0.03640	0.51460	−0.09860	0.1350*
H28	−0.14650	0.29610	−0.12420	0.1090*
H29	−0.37800	0.33920	−0.13480	0.1480*
H30	−0.50350	0.40210	−0.06960	0.1580*
H31	−0.39650	0.42580	0.00770	0.1360*
H32	−0.16250	0.39550	0.01810	0.1040*
H1O1	0.58880	0.21010	0.14080	0.1050*
H33A	0.54660	−0.00260	0.05560	0.1850*
H33B	0.68740	0.01800	0.03050	0.1850*
H33C	0.56890	0.11660	0.02310	0.1850*
H34A	0.72020	0.07050	0.11070	0.1250*
H34B	0.72300	0.19470	0.07970	0.1250*

	U11	U22	U33	U12	U13	U23
N1	0.0568 (13)	0.0751 (15)	0.0579 (12)	−0.0092 (11)	−0.0105 (10)	0.0180 (11)
N2	0.0557 (12)	0.0555 (12)	0.0498 (11)	0.0006 (9)	0.0064 (9)	0.0116 (9)
N3	0.0465 (11)	0.0519 (11)	0.0440 (10)	−0.0024 (9)	0.0030 (8)	0.0078 (8)
N4	0.0756 (16)	0.0745 (15)	0.0568 (13)	0.0038 (12)	−0.0105 (11)	0.0201 (11)
C1	0.0643 (18)	0.100 (2)	0.0722 (18)	−0.0165 (16)	−0.0235 (14)	0.0295 (17)
C2	0.0559 (16)	0.097 (2)	0.0814 (19)	−0.0211 (15)	−0.0158 (14)	0.0271 (17)
C3	0.0530 (14)	0.0703 (16)	0.0584 (14)	−0.0112 (12)	−0.0029 (11)	0.0142 (12)
C4	0.0472 (12)	0.0501 (13)	0.0446 (11)	0.0007 (10)	0.0030 (9)	0.0015 (10)
C5	0.0472 (12)	0.0455 (12)	0.0402 (11)	0.0017 (9)	0.0044 (9)	0.0018 (9)
C6	0.0459 (12)	0.0442 (12)	0.0443 (11)	0.0012 (9)	0.0043 (9)	0.0014 (9)
C7	0.0453 (12)	0.0473 (12)	0.0437 (11)	0.0015 (9)	0.0038 (9)	0.0019 (9)
C8	0.0486 (12)	0.0433 (12)	0.0433 (11)	0.0016 (9)	0.0057 (9)	0.0017 (9)
C9	0.0497 (13)	0.0487 (13)	0.0426 (11)	0.0006 (10)	−0.0006 (9)	0.0038 (9)
C10	0.0509 (14)	0.0713 (17)	0.0640 (15)	−0.0073 (12)	−0.0020 (11)	0.0173 (13)
C11	0.0546 (15)	0.083 (2)	0.0779 (19)	−0.0134 (14)	0.0052 (13)	0.0241 (15)
C12	0.0572 (15)	0.0674 (17)	0.0646 (15)	−0.0058 (12)	0.0074 (12)	0.0211 (13)
C13	0.0322 (10)	0.0375 (10)	0.0342 (9)	0.0020 (8)	0.0003 (7)	0.0060 (8)
C14	0.0487 (13)	0.0488 (13)	0.0432 (11)	0.0054 (10)	0.0011 (9)	−0.0005 (9)
C15	0.0484 (12)	0.0484 (13)	0.0430 (11)	0.0036 (10)	0.0007 (9)	0.0029 (9)
C16	0.0581 (15)	0.0708 (17)	0.0584 (15)	−0.0095 (13)	−0.0087 (12)	0.0167 (12)
C17	0.0700 (17)	0.0709 (18)	0.0641 (16)	−0.0164 (14)	−0.0090 (13)	0.0245 (14)
C18	0.0645 (15)	0.0572 (14)	0.0482 (12)	0.0040 (12)	−0.0043 (11)	0.0084 (11)
C19	0.0510 (14)	0.0660 (16)	0.0529 (13)	0.0001 (12)	−0.0055 (11)	0.0073 (12)
C20	0.0530 (14)	0.0604 (15)	0.0527 (13)	−0.0027 (11)	0.0019 (11)	0.0089 (11)
C21	0.090 (2)	0.081 (2)	0.0492 (14)	−0.0295 (17)	−0.0172 (14)	0.0199 (14)
C22	0.076 (2)	0.107 (3)	0.0690 (18)	−0.0173 (19)	0.0048 (15)	0.0109 (18)
C23	0.089 (2)	0.168 (4)	0.079 (2)	−0.035 (3)	0.0010 (19)	0.008 (2)
C24	0.127 (2)	0.136 (2)	0.113 (2)	−0.0215 (18)	0.0084 (17)	0.0141 (18)
C25	0.199 (5)	0.160 (5)	0.096 (3)	−0.080 (4)	−0.023 (3)	0.079 (3)
C26	0.165 (4)	0.094 (3)	0.077 (2)	−0.031 (3)	−0.020 (2)	0.036 (2)
C27	0.0789 (19)	0.0555 (15)	0.0655 (16)	0.0121 (13)	−0.0188 (14)	0.0001 (13)
C28	0.095 (2)	0.101 (3)	0.075 (2)	0.013 (2)	−0.0249 (18)	−0.0162 (18)
C29	0.105 (3)	0.154 (4)	0.106 (3)	0.024 (3)	−0.051 (3)	−0.034 (3)
C30	0.098 (3)	0.148 (4)	0.145 (4)	0.048 (3)	−0.041 (3)	−0.044 (3)
C31	0.104 (3)	0.119 (3)	0.115 (3)	0.054 (3)	−0.019 (2)	−0.031 (3)
C32	0.101 (2)	0.078 (2)	0.078 (2)	0.0311 (19)	−0.0226 (18)	−0.0157 (16)
O1	0.0663 (12)	0.0912 (14)	0.0521 (10)	−0.0245 (10)	0.0053 (8)	−0.0148 (9)
C33	0.098 (3)	0.174 (4)	0.097 (3)	−0.016 (3)	0.011 (2)	−0.060 (3)
C34	0.074 (2)	0.162 (4)	0.077 (2)	−0.028 (2)	0.0170 (17)	−0.036 (2)

O1—C34	1.379 (4)	C23—C24	1.390 (4)
O1—H1O1	0.8200	C24—C25	1.390 (3)
N1—C9	1.349 (3)	C25—C26	1.390 (3)
N1—C1	1.314 (4)	C27—C32	1.380 (4)
N2—C8	1.363 (3)	C27—C28	1.382 (3)
N2—C12	1.318 (4)	C28—C29	1.380 (5)
N3—C14	1.371 (3)	C29—C30	1.357 (7)
N3—C5	1.376 (3)	C30—C31	1.376 (7)
N4—C27	1.420 (3)	C31—C32	1.377 (6)
N4—C18	1.420 (3)	C1—H1	0.9300
N4—C21	1.419 (2)	C2—H2	0.9300
N3—H3N	0.94 (3)	C3—H3	0.9300
C1—C2	1.388 (4)	C10—H10	0.9300
C2—C3	1.362 (4)	C11—H11	0.9300
C3—C4	1.402 (4)	C12—H12	0.9300
C4—C9	1.417 (3)	C16—H16	0.9300
C4—C5	1.429 (3)	C17—H17	0.9300
C5—C6	1.377 (3)	C19—H19	0.9300
C6—C7	1.428 (3)	C20—H20	0.9300
C6—C13	1.377 (3)	C22—H22	0.9300
C7—C10	1.405 (4)	C23—H23	0.9300
C7—C8	1.403 (3)	C24—H24	0.9300
C8—C9	1.462 (3)	C25—H25	0.9300
C10—C11	1.363 (4)	C26—H26	0.9300
C11—C12	1.384 (4)	C28—H28	0.9300
C13—C14	1.325 (3)	C29—H29	0.9300
C14—C15	1.465 (3)	C30—H30	0.9300
C15—C20	1.382 (3)	C31—H31	0.9300
C15—C16	1.388 (4)	C32—H32	0.9300
C16—C17	1.381 (4)	C33—C34	1.459 (6)
C17—C18	1.378 (4)	C33—H33A	0.9600
C18—C19	1.388 (4)	C33—H33B	0.9600
C19—C20	1.377 (3)	C33—H33C	0.9600
C21—C22	1.390 (2)	C34—H34A	0.9700
C21—C26	1.390 (2)	C34—H34B	0.9700
C22—C23	1.390 (3)
C34—O1—H1O1	109.00	C27—C28—C29	119.9 (2)
C1—N1—C9	118.1 (2)	C28—C29—C30	121.2 (4)
C8—N2—C12	117.2 (2)	C29—C30—C31	119.4 (4)
C5—N3—C14	106.43 (18)	C30—C31—C32	120.2 (4)
C18—N4—C27	119.5 (2)	C27—C32—C31	120.5 (3)
C21—N4—C27	120.42 (17)	C2—C1—H1	118.00
C18—N4—C21	119.09 (19)	N1—C1—H1	118.00
C5—N3—H3N	127.2 (17)	C1—C2—H2	121.00
C14—N3—H3N	126.1 (17)	C3—C2—H2	121.00
N1—C1—C2	124.2 (3)	C4—C3—H3	120.00
C1—C2—C3	118.7 (3)	C2—C3—H3	120.00
C2—C3—C4	119.3 (3)	C7—C10—H10	121.00
C3—C4—C9	117.9 (2)	C11—C10—H10	121.00
C5—C4—C9	116.64 (18)	C10—C11—H11	120.00
C3—C4—C5	125.5 (2)	C12—C11—H11	120.00
N3—C5—C6	105.78 (18)	C11—C12—H12	118.00
C4—C5—C6	123.0 (2)	N2—C12—H12	118.00
N3—C5—C4	131.23 (19)	C17—C16—H16	120.00
C7—C6—C13	127.94 (18)	C15—C16—H16	120.00
C5—C6—C13	110.77 (19)	C16—C17—H17	119.00
C5—C6—C7	121.29 (19)	C18—C17—H17	119.00
C6—C7—C10	123.7 (2)	C20—C19—H19	120.00
C8—C7—C10	118.4 (2)	C18—C19—H19	120.00
C6—C7—C8	117.89 (18)	C15—C20—H20	119.00
N2—C8—C7	122.14 (18)	C19—C20—H20	119.00
C7—C8—C9	120.63 (19)	C23—C22—H22	120.00
N2—C8—C9	117.23 (18)	C21—C22—H22	120.00
N1—C9—C4	121.75 (19)	C22—C23—H23	120.00
C4—C9—C8	120.56 (18)	C24—C23—H23	120.00
N1—C9—C8	117.67 (19)	C23—C24—H24	120.00
C7—C10—C11	118.6 (3)	C25—C24—H24	120.00
C10—C11—C12	119.2 (3)	C26—C25—H25	120.00
N2—C12—C11	124.5 (3)	C24—C25—H25	120.00
C6—C13—C14	104.62 (17)	C25—C26—H26	120.00
C13—C14—C15	123.75 (18)	C21—C26—H26	120.00
N3—C14—C15	123.84 (18)	C27—C28—H28	120.00
N3—C14—C13	112.40 (19)	C29—C28—H28	120.00
C14—C15—C16	123.4 (2)	C28—C29—H29	119.00
C14—C15—C20	118.46 (19)	C30—C29—H29	119.00
C16—C15—C20	118.1 (2)	C31—C30—H30	120.00
C15—C16—C17	120.3 (3)	C29—C30—H30	120.00
C16—C17—C18	121.5 (3)	C30—C31—H31	120.00
C17—C18—C19	118.1 (2)	C32—C31—H31	120.00
N4—C18—C17	121.6 (2)	C31—C32—H32	120.00
N4—C18—C19	120.3 (2)	C27—C32—H32	120.00
C18—C19—C20	120.5 (2)	O1—C34—C33	110.6 (3)
C15—C20—C19	121.4 (2)	C34—C33—H33A	110.00
N4—C21—C22	121.14 (16)	C34—C33—H33B	109.00
C22—C21—C26	120.00 (14)	C34—C33—H33C	109.00
N4—C21—C26	118.86 (16)	H33A—C33—H33B	109.00
C21—C22—C23	120.0 (2)	H33A—C33—H33C	109.00
C22—C23—C24	120.0 (2)	H33B—C33—H33C	109.00
C23—C24—C25	119.99 (18)	O1—C34—H34A	109.00
C24—C25—C26	120.0 (2)	O1—C34—H34B	110.00
C21—C26—C25	120.03 (16)	C33—C34—H34A	110.00
N4—C27—C28	120.60 (16)	C33—C34—H34B	110.00
C28—C27—C32	118.8 (2)	H34A—C34—H34B	108.00
N4—C27—C32	120.6 (2)
C9—N1—C1—C2	0.1 (4)	C6—C7—C8—N2	179.0 (2)
C1—N1—C9—C8	−178.3 (2)	C10—C7—C8—N2	−0.7 (3)
C1—N1—C9—C4	−0.1 (3)	C6—C7—C8—C9	−0.4 (3)
C12—N2—C8—C7	0.6 (3)	C6—C7—C10—C11	−179.6 (2)
C12—N2—C8—C9	179.9 (2)	C8—C7—C10—C11	0.1 (4)
C8—N2—C12—C11	0.3 (4)	C10—C7—C8—C9	179.9 (2)
C5—N3—C14—C15	179.6 (2)	N2—C8—C9—C4	−178.8 (2)
C14—N3—C5—C4	−178.7 (2)	C7—C8—C9—N1	178.8 (2)
C14—N3—C5—C6	0.1 (2)	N2—C8—C9—N1	−0.6 (3)
C5—N3—C14—C13	0.0 (2)	C7—C8—C9—C4	0.6 (3)
C27—N4—C21—C26	49.8 (3)	C7—C10—C11—C12	0.7 (4)
C27—N4—C18—C17	−148.4 (2)	C10—C11—C12—N2	−0.9 (5)
C27—N4—C21—C22	−129.95 (19)	C6—C13—C14—C15	−179.7 (2)
C18—N4—C21—C26	−141.73 (19)	C6—C13—C14—N3	−0.1 (2)
C21—N4—C18—C17	43.0 (3)	N3—C14—C15—C16	−8.0 (4)
C18—N4—C27—C28	−135.0 (2)	N3—C14—C15—C20	172.2 (2)
C18—N4—C27—C32	44.3 (3)	C13—C14—C15—C20	−8.3 (3)
C18—N4—C21—C22	38.6 (3)	C13—C14—C15—C16	171.5 (2)
C21—N4—C27—C28	33.5 (3)	C16—C15—C20—C19	−0.3 (3)
C27—N4—C18—C19	31.7 (3)	C20—C15—C16—C17	0.6 (4)
C21—N4—C18—C19	−136.9 (2)	C14—C15—C20—C19	179.5 (2)
C21—N4—C27—C32	−147.3 (2)	C14—C15—C16—C17	−179.2 (2)
N1—C1—C2—C3	−0.1 (5)	C15—C16—C17—C18	−0.4 (4)
C1—C2—C3—C4	0.1 (4)	C16—C17—C18—N4	180.0 (3)
C2—C3—C4—C5	179.0 (3)	C16—C17—C18—C19	−0.1 (4)
C2—C3—C4—C9	−0.1 (4)	C17—C18—C19—C20	0.4 (4)
C9—C4—C5—C6	1.2 (3)	N4—C18—C19—C20	−179.7 (2)
C5—C4—C9—C8	−1.0 (3)	C18—C19—C20—C15	−0.2 (4)
C3—C4—C5—N3	0.7 (4)	N4—C21—C22—C23	179.69 (17)
C3—C4—C5—C6	−177.9 (2)	C26—C21—C22—C23	0.0 (3)
C3—C4—C9—N1	0.1 (3)	N4—C21—C26—C25	−179.69 (18)
C3—C4—C9—C8	178.2 (2)	C22—C21—C26—C25	0.0 (3)
C5—C4—C9—N1	−179.1 (2)	C21—C22—C23—C24	0.0 (3)
C9—C4—C5—N3	179.8 (2)	C22—C23—C24—C25	0.0 (3)
C4—C5—C6—C7	−1.1 (3)	C23—C24—C25—C26	0.1 (3)
N3—C5—C6—C13	−0.2 (2)	C24—C25—C26—C21	0.0 (3)
C4—C5—C6—C13	178.7 (2)	N4—C27—C28—C29	−179.8 (3)
N3—C5—C6—C7	−179.94 (19)	C32—C27—C28—C29	0.9 (4)
C13—C6—C7—C8	−179.1 (2)	N4—C27—C32—C31	−178.0 (3)
C5—C6—C7—C8	0.6 (3)	C28—C27—C32—C31	1.2 (4)
C7—C6—C13—C14	179.9 (2)	C27—C28—C29—C30	−1.9 (6)
C5—C6—C7—C10	−179.7 (2)	C28—C29—C30—C31	0.7 (8)
C5—C6—C13—C14	0.2 (2)	C29—C30—C31—C32	1.5 (7)
C13—C6—C7—C10	0.5 (4)	C30—C31—C32—C27	−2.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.94 (3)	1.84 (3)	2.777 (3)	175 (2)
O1—H1O1···N1i	0.82	2.15	2.819 (3)	139
O1—H1O1···N2i	0.82	2.38	3.087 (3)	145
C16—H16···O1	0.93	2.54	3.419 (4)	157
C3—H3···N2i	0.93	2.59	3.310 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.94 (3)	1.84 (3)	2.777 (3)	175 (2)
O1—H1O1⋯N1i	0.82	2.15	2.819 (3)	139
O1—H1O1⋯N2i	0.82	2.38	3.087 (3)	145
C16—H16⋯O1	0.93	2.54	3.419 (4)	157
C3—H3⋯N2i	0.93	2.59	3.310 (4)	135

Symmetry code: (i) .