4-(4-Chloro-phen-yl)-6-meth-oxy-2,2'-bipyridine-5-carbonitrile.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(18)H(12)ClN(3)O. The two pyridine rings are almost coplanar [dihedral angles between the rings: 2.87 (15) and 5.36 (16)°] while the chloro-phenyl rings are twisted out of the plane of the adjacent bipyridine ring by 44.1 (1) and 43.8 (1)° in the two mol-ecules. The crystal packing is stabilized by C-H⋯N and C-H⋯Cl inter-actions.

Related literature

Pyridine derivatives possess phospho­diesterase-inhibiting (Heintzelman et al., 2003a ▶,b ▶), anti­fungal (Cook et al., 2004a ▶,b ▶), anti­fertility (Upton et al., 2000 ▶) and anti­arrhythmic activities (Ellefson et al., 1978 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H12ClN3O

M = 321.76

Monoclinic,

a = 9.5869 (5) Å

b = 13.8761 (7) Å

c = 12.2124 (6) Å

β = 106.896 (2)°

V = 1554.47 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.927, T max = 0.951

17581 measured reflections

6950 independent reflections

4300 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.00

6950 reflections

417 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 3268 Friedel pairs

Flack parameter: 0.05 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012409/bt2899sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012409/bt2899Isup2.hkl

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

C18H12ClN3O	F(000) = 664
Mr = 321.76	Dx = 1.375 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3721 reflections
a = 9.5869 (5) Å	θ = 1.7–27.5°
b = 13.8761 (7) Å	µ = 0.25 mm−1
c = 12.2124 (6) Å	T = 293 K
β = 106.896 (2)°	Block, colorless
V = 1554.47 (14) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	6950 independent reflections
Radiation source: fine-focus sealed tube	4300 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω and φ scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
Tmin = 0.927, Tmax = 0.951	k = −17→17
17581 measured reflections	l = −15→15

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.1394P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
6950 reflections	Δρmax = 0.24 e Å−3
417 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 3268 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (6)

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
C2'	−0.0524 (3)	0.2747 (2)	0.5616 (2)	0.0453 (7)
C2	−0.1641 (3)	0.5282 (2)	0.7627 (2)	0.0485 (7)
C3'	0.0529 (3)	0.2755 (2)	0.66886 (19)	0.0438 (6)
C3	−0.0610 (3)	0.5309 (2)	0.86978 (19)	0.0448 (6)
C4'	0.1994 (3)	0.2704 (2)	0.67256 (19)	0.0450 (6)
C4	0.0852 (3)	0.53628 (19)	0.87589 (19)	0.0427 (6)
C5	0.1208 (3)	0.5349 (2)	0.77260 (19)	0.0452 (6)
H5	0.2177	0.5373	0.7726	0.054*
C5'	0.2306 (3)	0.2696 (2)	0.56900 (19)	0.0467 (6)
H5'	0.3271	0.2672	0.5679	0.056*
C6	0.0109 (3)	0.5301 (2)	0.6710 (2)	0.0439 (6)
C6'	0.1199 (3)	0.2723 (2)	0.4671 (2)	0.0430 (6)
C7'	−0.3014 (3)	0.2777 (3)	0.4542 (2)	0.0730 (9)
H7D	−0.2843	0.3307	0.4092	0.110*
H7F	−0.3957	0.2845	0.4658	0.110*
H7E	−0.2977	0.2183	0.4147	0.110*
C7	−0.4109 (3)	0.5274 (3)	0.6510 (2)	0.0769 (10)
H7A	−0.3862	0.5766	0.6046	0.115*
H7B	−0.5054	0.5407	0.6598	0.115*
H7C	−0.4125	0.4659	0.6147	0.115*
C8'	0.0057 (3)	0.2856 (2)	0.7694 (2)	0.0506 (7)
C8	−0.1112 (3)	0.5223 (2)	0.9698 (2)	0.0509 (7)
C10	0.2010 (3)	0.5420 (2)	0.9863 (2)	0.0452 (7)
C10'	0.3164 (3)	0.2671 (2)	0.78201 (19)	0.0451 (6)
C11	0.1893 (3)	0.6056 (2)	1.0710 (2)	0.0488 (7)
H11	0.1081	0.6455	1.0575	0.059*
C11'	0.3071 (3)	0.2046 (2)	0.8686 (2)	0.0540 (7)
H11'	0.2262	0.1646	0.8573	0.065*
C12'	0.4158 (3)	0.2011 (2)	0.9709 (2)	0.0601 (8)
H12'	0.4089	0.1587	1.0281	0.072*
C12	0.2950 (3)	0.6106 (2)	1.1738 (2)	0.0540 (7)
H12	0.2867	0.6538	1.2298	0.065*
C13'	0.5332 (3)	0.2601 (3)	0.9877 (2)	0.0609 (9)
C13	0.4138 (3)	0.5507 (3)	1.1932 (2)	0.0565 (8)
C14	0.4309 (3)	0.4900 (3)	1.1102 (2)	0.0646 (9)
H14	0.5141	0.4520	1.1233	0.078*
C14'	0.5486 (3)	0.3210 (3)	0.9047 (3)	0.0661 (9)
H14'	0.6307	0.3600	0.9172	0.079*
C15'	0.4401 (3)	0.3240 (2)	0.8012 (2)	0.0567 (8)
H15'	0.4504	0.3648	0.7436	0.068*
C15	0.3241 (3)	0.4854 (2)	1.0067 (2)	0.0572 (8)
H15	0.3351	0.4438	0.9501	0.069*
C16	0.0424 (3)	0.5259 (2)	0.5593 (2)	0.0454 (7)
C16'	0.1494 (3)	0.2756 (2)	0.3547 (2)	0.0464 (6)
C18'	0.3136 (4)	0.2815 (3)	0.2542 (3)	0.0821 (11)
H18'	0.4099	0.2807	0.2524	0.098*
C18	0.2082 (4)	0.5207 (3)	0.4595 (3)	0.0717 (10)
H18	0.3052	0.5202	0.4594	0.086*
C19	0.1032 (4)	0.5161 (2)	0.3559 (3)	0.0662 (10)
H19	0.1284	0.5128	0.2880	0.079*
C19'	0.2062 (4)	0.2900 (3)	0.1528 (2)	0.0715 (10)
H19'	0.2299	0.2950	0.0844	0.086*
C20'	0.0658 (4)	0.2910 (3)	0.1527 (2)	0.0643 (9)
H20'	−0.0091	0.2968	0.0848	0.077*
C20	−0.0384 (4)	0.5166 (3)	0.3552 (2)	0.0629 (9)
H20	−0.1127	0.5133	0.2866	0.075*
C21	−0.0705 (3)	0.5222 (2)	0.4585 (2)	0.0554 (7)
H21	−0.1668	0.5236	0.4601	0.067*
C21'	0.0364 (3)	0.2832 (2)	0.2554 (2)	0.0550 (8)
H21'	−0.0596	0.2831	0.2581	0.066*
N1	−0.1311 (2)	0.52769 (17)	0.66537 (16)	0.0476 (6)
N1'	−0.0218 (2)	0.27322 (17)	0.46358 (16)	0.0477 (5)
N9'	−0.0333 (3)	0.2959 (2)	0.8486 (2)	0.0696 (8)
N9	−0.1527 (3)	0.5130 (2)	1.0466 (2)	0.0711 (8)
N17'	0.2879 (3)	0.2742 (2)	0.35573 (18)	0.0655 (7)
N17	0.1810 (3)	0.5257 (2)	0.56052 (18)	0.0594 (7)
O1	−0.3049 (2)	0.52612 (18)	0.76094 (15)	0.0623 (6)
O1'	−0.1919 (2)	0.27689 (18)	0.56248 (16)	0.0617 (6)
Cl1'	0.66572 (10)	0.25841 (9)	1.11925 (7)	0.0970 (4)
Cl1	0.54493 (9)	0.55353 (8)	1.32596 (6)	0.0888 (3)

	U11	U22	U33	U12	U13	U23
C2'	0.0455 (16)	0.0402 (16)	0.0507 (15)	−0.0023 (15)	0.0149 (12)	0.0032 (13)
C2	0.0441 (15)	0.0460 (17)	0.0545 (15)	−0.0014 (14)	0.0130 (12)	0.0042 (14)
C3'	0.0524 (16)	0.0416 (16)	0.0372 (13)	−0.0055 (15)	0.0126 (11)	0.0029 (14)
C3	0.0522 (16)	0.0423 (15)	0.0408 (13)	0.0036 (14)	0.0149 (11)	0.0003 (13)
C4'	0.0522 (15)	0.0395 (15)	0.0422 (13)	−0.0043 (15)	0.0121 (11)	0.0023 (14)
C4	0.0472 (15)	0.0382 (15)	0.0422 (13)	0.0042 (13)	0.0120 (11)	−0.0021 (13)
C5	0.0436 (14)	0.0473 (16)	0.0448 (13)	0.0024 (13)	0.0130 (10)	−0.0011 (13)
C5'	0.0505 (15)	0.0454 (16)	0.0433 (13)	0.0005 (14)	0.0122 (11)	0.0043 (13)
C6	0.0504 (16)	0.0392 (15)	0.0416 (13)	−0.0009 (13)	0.0128 (11)	−0.0008 (13)
C6'	0.0496 (16)	0.0355 (14)	0.0427 (13)	0.0009 (14)	0.0113 (11)	0.0023 (13)
C7'	0.0506 (17)	0.090 (3)	0.0700 (19)	0.002 (2)	0.0034 (14)	0.000 (2)
C7	0.0470 (17)	0.102 (3)	0.074 (2)	−0.010 (2)	0.0058 (14)	0.011 (2)
C8'	0.0565 (18)	0.0444 (19)	0.0512 (16)	−0.0023 (16)	0.0161 (14)	0.0052 (14)
C8	0.0524 (16)	0.0514 (18)	0.0482 (15)	0.0058 (15)	0.0137 (12)	−0.0002 (15)
C10	0.0432 (15)	0.0486 (17)	0.0427 (13)	−0.0014 (14)	0.0108 (11)	0.0027 (14)
C10'	0.0512 (15)	0.0468 (15)	0.0377 (12)	−0.0019 (14)	0.0135 (10)	−0.0030 (13)
C11	0.0535 (17)	0.0529 (17)	0.0414 (14)	0.0028 (14)	0.0159 (12)	−0.0007 (13)
C11'	0.0587 (18)	0.0557 (18)	0.0451 (15)	−0.0016 (14)	0.0110 (12)	0.0012 (14)
C12'	0.068 (2)	0.066 (2)	0.0444 (15)	0.0144 (17)	0.0133 (14)	0.0025 (15)
C12	0.0605 (18)	0.0609 (19)	0.0416 (14)	−0.0107 (16)	0.0167 (13)	−0.0050 (13)
C13'	0.0528 (18)	0.076 (2)	0.0464 (15)	0.0167 (18)	0.0034 (13)	−0.0115 (17)
C13	0.0516 (17)	0.069 (2)	0.0411 (14)	−0.0138 (17)	0.0015 (12)	0.0058 (16)
C14	0.0552 (19)	0.068 (2)	0.0638 (19)	0.0076 (17)	0.0063 (16)	0.0046 (18)
C14'	0.0426 (17)	0.078 (2)	0.074 (2)	−0.0076 (16)	0.0120 (16)	−0.0202 (19)
C15'	0.0550 (18)	0.060 (2)	0.0569 (17)	−0.0061 (15)	0.0200 (14)	−0.0035 (15)
C15	0.0569 (18)	0.057 (2)	0.0541 (16)	0.0098 (15)	0.0107 (14)	−0.0035 (15)
C16	0.0549 (17)	0.0386 (16)	0.0418 (14)	−0.0049 (15)	0.0124 (12)	−0.0012 (13)
C16'	0.0569 (16)	0.0394 (15)	0.0427 (13)	−0.0013 (15)	0.0143 (11)	−0.0003 (13)
C18'	0.076 (2)	0.122 (3)	0.0567 (18)	0.010 (2)	0.0321 (16)	0.009 (2)
C18	0.077 (2)	0.083 (3)	0.065 (2)	−0.008 (2)	0.0367 (18)	−0.004 (2)
C19	0.097 (3)	0.059 (2)	0.0525 (18)	−0.012 (2)	0.0378 (18)	−0.0001 (16)
C19'	0.094 (3)	0.081 (3)	0.0451 (16)	0.003 (2)	0.0294 (17)	0.0030 (18)
C20'	0.083 (2)	0.065 (2)	0.0393 (15)	−0.0019 (19)	0.0100 (15)	−0.0059 (16)
C20	0.085 (2)	0.058 (2)	0.0422 (16)	−0.0044 (19)	0.0135 (16)	0.0041 (15)
C21	0.0601 (18)	0.0571 (19)	0.0465 (15)	0.0019 (16)	0.0113 (12)	0.0031 (14)
C21'	0.0580 (17)	0.062 (2)	0.0438 (15)	−0.0013 (16)	0.0121 (12)	−0.0027 (15)
N1	0.0496 (13)	0.0515 (15)	0.0400 (11)	−0.0026 (12)	0.0102 (9)	0.0012 (11)
N1'	0.0509 (13)	0.0470 (13)	0.0436 (12)	−0.0002 (13)	0.0113 (10)	0.0018 (11)
N9'	0.093 (2)	0.0659 (19)	0.0600 (16)	−0.0049 (15)	0.0382 (15)	0.0010 (14)
N9	0.0778 (18)	0.084 (2)	0.0598 (15)	0.0023 (16)	0.0336 (13)	−0.0006 (15)
N17'	0.0601 (16)	0.089 (2)	0.0499 (13)	0.0088 (17)	0.0201 (11)	0.0099 (15)
N17	0.0592 (15)	0.0710 (18)	0.0500 (13)	−0.0052 (15)	0.0190 (11)	−0.0064 (14)
O1	0.0460 (11)	0.0844 (17)	0.0555 (11)	−0.0024 (12)	0.0132 (9)	0.0104 (12)
O1'	0.0462 (11)	0.0785 (16)	0.0605 (12)	0.0000 (12)	0.0160 (9)	−0.0005 (12)
Cl1'	0.0709 (5)	0.1312 (9)	0.0664 (5)	0.0322 (6)	−0.0157 (4)	−0.0216 (6)
Cl1	0.0726 (5)	0.1207 (8)	0.0551 (4)	−0.0156 (5)	−0.0101 (3)	0.0127 (5)

C2'—N1'	1.313 (3)	C11—H11	0.9300
C2'—O1'	1.341 (3)	C11'—C12'	1.375 (3)
C2'—C3'	1.403 (3)	C11'—H11'	0.9300
C2—N1	1.316 (3)	C12'—C13'	1.358 (5)
C2—O1	1.344 (3)	C12'—H12'	0.9300
C2—C3	1.391 (3)	C12—C13	1.374 (4)
C3'—C4'	1.394 (3)	C12—H12	0.9300
C3'—C8'	1.433 (4)	C13'—C14'	1.361 (5)
C3—C4	1.384 (3)	C13'—Cl1'	1.735 (3)
C3—C8	1.442 (4)	C13—C14	1.364 (4)
C4'—C5'	1.382 (3)	C13—Cl1	1.739 (3)
C4'—C10'	1.475 (3)	C14—C15	1.378 (4)
C4—C5	1.399 (3)	C14—H14	0.9300
C4—C10	1.478 (3)	C14'—C15'	1.384 (4)
C5—C6	1.376 (3)	C14'—H14'	0.9300
C5—H5	0.9300	C15'—H15'	0.9300
C5'—C6'	1.382 (3)	C15—H15	0.9300
C5'—H5'	0.9300	C16—N17	1.324 (3)
C6—N1	1.343 (3)	C16—C21	1.384 (3)
C6—C16	1.481 (3)	C16'—N17'	1.325 (3)
C6'—N1'	1.346 (3)	C16'—C21'	1.376 (3)
C6'—C16'	1.481 (3)	C18'—N17'	1.337 (4)
C7'—O1'	1.430 (3)	C18'—C19'	1.366 (4)
C7'—H7D	0.9600	C18'—H18'	0.9300
C7'—H7F	0.9600	C18—N17	1.335 (3)
C7'—H7E	0.9600	C18—C19	1.370 (4)
C7—O1	1.430 (3)	C18—H18	0.9300
C7—H7A	0.9600	C19—C20	1.355 (4)
C7—H7B	0.9600	C19—H19	0.9300
C7—H7C	0.9600	C19'—C20'	1.346 (4)
C8'—N9'	1.143 (4)	C19'—H19'	0.9300
C8—N9	1.127 (3)	C20'—C21'	1.367 (4)
C10—C15	1.379 (4)	C20'—H20'	0.9300
C10—C11	1.388 (4)	C20—C21	1.384 (4)
C10'—C15'	1.387 (4)	C20—H20	0.9300
C10'—C11'	1.391 (4)	C21—H21	0.9300
C11—C12	1.368 (4)	C21'—H21'	0.9300
N1'—C2'—O1'	119.7 (2)	C11'—C12'—H12'	120.3
N1'—C2'—C3'	124.1 (2)	C11—C12—C13	118.9 (3)
O1'—C2'—C3'	116.2 (2)	C11—C12—H12	120.5
N1—C2—O1	119.3 (2)	C13—C12—H12	120.5
N1—C2—C3	123.9 (2)	C12'—C13'—C14'	121.7 (3)
O1—C2—C3	116.8 (2)	C12'—C13'—Cl1'	118.9 (3)
C4'—C3'—C2'	118.4 (2)	C14'—C13'—Cl1'	119.3 (3)
C4'—C3'—C8'	122.9 (2)	C14—C13—C12	121.2 (2)
C2'—C3'—C8'	118.7 (2)	C14—C13—Cl1	119.8 (3)
C4—C3—C2	118.9 (2)	C12—C13—Cl1	119.0 (2)
C4—C3—C8	122.8 (2)	C13—C14—C15	119.5 (3)
C2—C3—C8	118.2 (2)	C13—C14—H14	120.2
C5'—C4'—C3'	117.0 (2)	C15—C14—H14	120.2
C5'—C4'—C10'	121.3 (2)	C13'—C14'—C15'	118.9 (3)
C3'—C4'—C10'	121.6 (2)	C13'—C14'—H14'	120.5
C3—C4—C5	117.3 (2)	C15'—C14'—H14'	120.5
C3—C4—C10	122.1 (2)	C14'—C15'—C10'	121.0 (3)
C5—C4—C10	120.5 (2)	C14'—C15'—H15'	119.5
C6—C5—C4	119.4 (2)	C10'—C15'—H15'	119.5
C6—C5—H5	120.3	C14—C15—C10	120.6 (3)
C4—C5—H5	120.3	C14—C15—H15	119.7
C4'—C5'—C6'	120.7 (2)	C10—C15—H15	119.7
C4'—C5'—H5'	119.7	N17—C16—C21	122.2 (2)
C6'—C5'—H5'	119.7	N17—C16—C6	117.5 (2)
N1—C6—C5	123.1 (2)	C21—C16—C6	120.3 (2)
N1—C6—C16	115.3 (2)	N17'—C16'—C21'	122.7 (2)
C5—C6—C16	121.6 (2)	N17'—C16'—C6'	116.9 (2)
N1'—C6'—C5'	122.2 (2)	C21'—C16'—C6'	120.4 (3)
N1'—C6'—C16'	115.6 (2)	N17'—C18'—C19'	123.6 (3)
C5'—C6'—C16'	122.1 (2)	N17'—C18'—H18'	118.2
O1'—C7'—H7D	109.5	C19'—C18'—H18'	118.2
O1'—C7'—H7F	109.5	N17—C18—C19	124.5 (3)
H7D—C7'—H7F	109.5	N17—C18—H18	117.7
O1'—C7'—H7E	109.5	C19—C18—H18	117.7
H7D—C7'—H7E	109.5	C20—C19—C18	118.1 (3)
H7F—C7'—H7E	109.5	C20—C19—H19	120.9
O1—C7—H7A	109.5	C18—C19—H19	120.9
O1—C7—H7B	109.5	C20'—C19'—C18'	119.5 (3)
H7A—C7—H7B	109.5	C20'—C19'—H19'	120.3
O1—C7—H7C	109.5	C18'—C19'—H19'	120.3
H7A—C7—H7C	109.5	C19'—C20'—C21'	118.1 (3)
H7B—C7—H7C	109.5	C19'—C20'—H20'	120.9
N9'—C8'—C3'	178.3 (4)	C21'—C20'—H20'	120.9
N9—C8—C3	177.9 (3)	C19—C20—C21	118.8 (3)
C15—C10—C11	118.5 (2)	C19—C20—H20	120.6
C15—C10—C4	120.7 (2)	C21—C20—H20	120.6
C11—C10—C4	120.8 (2)	C16—C21—C20	119.3 (3)
C15'—C10'—C11'	117.9 (2)	C16—C21—H21	120.4
C15'—C10'—C4'	121.6 (2)	C20—C21—H21	120.4
C11'—C10'—C4'	120.6 (2)	C20'—C21'—C16'	119.7 (3)
C12—C11—C10	121.2 (3)	C20'—C21'—H21'	120.2
C12—C11—H11	119.4	C16'—C21'—H21'	120.2
C10—C11—H11	119.4	C2—N1—C6	117.4 (2)
C12'—C11'—C10'	120.9 (3)	C2'—N1'—C6'	117.50 (19)
C12'—C11'—H11'	119.6	C16'—N17'—C18'	116.4 (3)
C10'—C11'—H11'	119.6	C16—N17—C18	117.1 (2)
C13'—C12'—C11'	119.5 (3)	C2—O1—C7	116.9 (2)
C13'—C12'—H12'	120.3	C2'—O1'—C7'	117.3 (2)
N1'—C2'—C3'—C4'	−2.8 (5)	C12—C13—C14—C15	−3.0 (5)
O1'—C2'—C3'—C4'	178.1 (3)	Cl1—C13—C14—C15	177.6 (2)
N1'—C2'—C3'—C8'	174.6 (3)	C12'—C13'—C14'—C15'	1.2 (5)
O1'—C2'—C3'—C8'	−4.5 (4)	Cl1'—C13'—C14'—C15'	−178.0 (2)
N1—C2—C3—C4	2.0 (4)	C13'—C14'—C15'—C10'	0.8 (5)
O1—C2—C3—C4	−178.0 (3)	C11'—C10'—C15'—C14'	−2.1 (4)
N1—C2—C3—C8	−174.4 (3)	C4'—C10'—C15'—C14'	179.4 (3)
O1—C2—C3—C8	5.6 (4)	C13—C14—C15—C10	0.5 (5)
C2'—C3'—C4'—C5'	3.1 (4)	C11—C10—C15—C14	1.8 (4)
C8'—C3'—C4'—C5'	−174.2 (3)	C4—C10—C15—C14	−179.2 (3)
C2'—C3'—C4'—C10'	−177.7 (3)	N1—C6—C16—N17	−178.4 (3)
C8'—C3'—C4'—C10'	5.1 (5)	C5—C6—C16—N17	0.8 (4)
C2—C3—C4—C5	−2.4 (4)	N1—C6—C16—C21	1.6 (4)
C8—C3—C4—C5	173.8 (3)	C5—C6—C16—C21	−179.2 (3)
C2—C3—C4—C10	178.3 (3)	N1'—C6'—C16'—N17'	−179.6 (3)
C8—C3—C4—C10	−5.4 (4)	C5'—C6'—C16'—N17'	1.2 (4)
C3—C4—C5—C6	1.1 (4)	N1'—C6'—C16'—C21'	2.5 (4)
C10—C4—C5—C6	−179.6 (3)	C5'—C6'—C16'—C21'	−176.7 (3)
C3'—C4'—C5'—C6'	−1.0 (4)	N17—C18—C19—C20	−0.1 (6)
C10'—C4'—C5'—C6'	179.7 (3)	N17'—C18'—C19'—C20'	−0.2 (7)
C4—C5—C6—N1	0.8 (4)	C18'—C19'—C20'—C21'	−0.1 (6)
C4—C5—C6—C16	−178.3 (3)	C18—C19—C20—C21	0.3 (5)
C4'—C5'—C6'—N1'	−1.8 (4)	N17—C16—C21—C20	1.1 (5)
C4'—C5'—C6'—C16'	177.4 (3)	C6—C16—C21—C20	−178.9 (3)
C4'—C3'—C8'—N9'	116 (12)	C19—C20—C21—C16	−0.8 (5)
C2'—C3'—C8'—N9'	−62 (12)	C19'—C20'—C21'—C16'	0.6 (5)
C4—C3—C8—N9	−124 (9)	N17'—C16'—C21'—C20'	−0.9 (5)
C2—C3—C8—N9	52 (9)	C6'—C16'—C21'—C20'	176.8 (3)
C3—C4—C10—C15	134.3 (3)	O1—C2—N1—C6	179.8 (3)
C5—C4—C10—C15	−45.0 (4)	C3—C2—N1—C6	−0.2 (4)
C3—C4—C10—C11	−46.8 (4)	C5—C6—N1—C2	−1.2 (4)
C5—C4—C10—C11	134.0 (3)	C16—C6—N1—C2	177.9 (2)
C5'—C4'—C10'—C15'	45.0 (4)	O1'—C2'—N1'—C6'	179.2 (3)
C3'—C4'—C10'—C15'	−134.2 (3)	C3'—C2'—N1'—C6'	0.1 (5)
C5'—C4'—C10'—C11'	−133.5 (3)	C5'—C6'—N1'—C2'	2.2 (4)
C3'—C4'—C10'—C11'	47.3 (4)	C16'—C6'—N1'—C2'	−177.0 (2)
C15—C10—C11—C12	−1.8 (4)	C21'—C16'—N17'—C18'	0.6 (5)
C4—C10—C11—C12	179.2 (3)	C6'—C16'—N17'—C18'	−177.2 (3)
C15'—C10'—C11'—C12'	1.4 (4)	C19'—C18'—N17'—C16'	0.0 (6)
C4'—C10'—C11'—C12'	179.9 (3)	C21—C16—N17—C18	−0.8 (5)
C10'—C11'—C12'—C13'	0.5 (4)	C6—C16—N17—C18	179.2 (3)
C10—C11—C12—C13	−0.6 (4)	C19—C18—N17—C16	0.3 (6)
C11'—C12'—C13'—C14'	−1.9 (5)	N1—C2—O1—C7	−2.6 (4)
C11'—C12'—C13'—Cl1'	177.3 (2)	C3—C2—O1—C7	177.5 (3)
C11—C12—C13—C14	3.0 (5)	N1'—C2'—O1'—C7'	−0.1 (4)
C11—C12—C13—Cl1	−177.5 (2)	C3'—C2'—O1'—C7'	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N9'i	0.93	2.58	3.321 (4)	137
C21—H21···Cl1ii	0.93	2.80	3.597 (3)	144
C11'—H11'···N9iii	0.93	2.60	3.349 (4)	138
C21'—H21'···Cl1'ii	0.93	2.71	3.475 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N9′i	0.93	2.58	3.321 (4)	137
C21—H21⋯Cl1ii	0.93	2.80	3.597 (3)	144
C11′—H11′⋯N9iii	0.93	2.60	3.349 (4)	138
C21′—H21′⋯Cl1′ii	0.93	2.71	3.475 (3)	140

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