5-(4-Chloro-phen-yl)-7-(4-methyl-phen-yl)-4-(pyrrolidin-1-yl)-7H-pyrrolo-[2,3-d]pyrimidine.

The title compound, C23H21ClN4, contains two molecules (A and B) in the asymmetric unit, which are related to one another by a pseudo-inversion center. The non-aromatic pyrrolidine ring in each independent mol-ecule adopts a half-chair conformation; the ring puckering parameters are θ = 0.407 (3) Å and ϕ = 270.5 (4)°, and the pseudo-rotation parameters are ρ = 72.5 (3)° and τ = 42.2 (2)° for an N-C bond of molecule A, and the corresponding values are 0.415 (3) Å, 271.6 (4)°, 73.6 (3)° and 42.6 (2)° for molecule B. The dihedral angles between the central fused-ring system and the substituted chlorophenyl and methylphenyl rings are 66.35 and 45.59°, respectively, for molecule A, and 64.51 and 41.89° for molecule B. The geometry of all four intramolecular C-H⋯π interactions are of type III. π-π interactions involving the centroids of symmetry-related pyrrole rings of molecule B are 4.390 Å, contributing further to the stability of the molecule.

Related literature

For background to and the biological activity of pyrrolo­[2,3-d]pyrimidines, see: Chadwick (1990 ▶); Hulzenlaub et al. (1972 ▶); Ohgi et al. (1979 ▶); Smith et al. (1972 ▶). For our crystallographic investigations of heterocyclic compounds, see: Patel et al. (2007 ▶, 2012 ▶). For C—H⋯π inter­actions, see: Malone et al. (1997 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H21ClN4

M = 388.72

Triclinic,

a = 8.967 (3) Å

b = 15.367 (5) Å

c = 15.960 (2) Å

α = 69.210 (17)°

β = 75.653 (16)°

γ = 76.52 (3)°

V = 1966.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.951, T max = 0.959

7458 measured reflections

6864 independent reflections

3569 reflections with I > 2σ(I)

R int = 0.027

2 standard reflections every 1 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.01

6864 reflections

507 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019168/gg2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019168/gg2114Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019168/gg2114Isup3.cml

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

C23H21ClN4	Z = 4
Mr = 388.72	F(000) = 816
Triclinic, P1	Dx = 1.313 Mg m−3Dm = 1.310 Mg m−3Dm measured by floatation method
Hall symbol: -P 1	Melting point: 433 K
a = 8.967 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.367 (5) Å	Cell parameters from 25 reflections
c = 15.960 (2) Å	θ = 10–25°
α = 69.210 (17)°	µ = 0.21 mm−1
β = 75.653 (16)°	T = 293 K
γ = 76.52 (3)°	Needle, white
V = 1966.2 (10) Å3	0.3 × 0.2 × 0.2 mm

Enraf–Nonius CAD-4 diffractometer	3569 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −17→18
Tmin = 0.951, Tmax = 0.959	l = −18→18
7458 measured reflections	2 standard reflections every 1 min
6909 independent reflections	intensity decay: none

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.227P] where P = (Fo2 + 2Fc2)/3
6864 reflections	(Δ/σ)max = 0.001
507 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.2724 (3)	0.05271 (17)	0.38941 (16)	0.0460 (7)
H2	0.2653	0.1114	0.3448	0.055*
C3	0.2482 (3)	0.03931 (16)	0.48054 (16)	0.0411 (6)
C4	0.2704 (3)	−0.06207 (16)	0.52460 (16)	0.0396 (6)
C5	0.2610 (3)	−0.12783 (17)	0.61396 (17)	0.0446 (6)
C7	0.3092 (3)	−0.24738 (18)	0.55056 (18)	0.0528 (7)
H7	0.3204	−0.3120	0.5614	0.063*
C9	0.3067 (3)	−0.10308 (17)	0.45445 (16)	0.0400 (6)
C10	0.3198 (3)	−0.04409 (17)	0.28547 (16)	0.0440 (6)
C11	0.4300 (3)	−0.11218 (19)	0.25792 (18)	0.0569 (8)
H11	0.4996	−0.1513	0.2955	0.068*
C12	0.4371 (4)	−0.12247 (19)	0.17456 (19)	0.0641 (8)
H12	0.5110	−0.1694	0.1572	0.077*
C13	0.3380 (4)	−0.0653 (2)	0.11640 (18)	0.0593 (8)
C14	0.2295 (4)	0.0028 (2)	0.14461 (19)	0.0673 (9)
H14	0.1615	0.0426	0.1063	0.081*
C15	0.2187 (3)	0.0137 (2)	0.22876 (17)	0.0576 (8)
H15	0.1434	0.0598	0.2467	0.069*
C16	0.3471 (5)	−0.0769 (2)	0.02497 (19)	0.0868 (11)
H161	0.4047	−0.1378	0.0243	0.130*
H162	0.3986	−0.0287	−0.0223	0.130*
H163	0.2437	−0.0716	0.0149	0.130*
C17	0.2019 (3)	0.11753 (16)	0.52038 (15)	0.0385 (6)
C18	0.3034 (3)	0.17926 (17)	0.50595 (17)	0.0469 (6)
H18	0.4013	0.1724	0.4697	0.056*
C19	0.2609 (4)	0.25081 (18)	0.54483 (18)	0.0547 (7)
H19	0.3304	0.2911	0.5357	0.066*
C20	0.1156 (4)	0.26198 (18)	0.59692 (17)	0.0526 (7)
C21	0.0117 (3)	0.20315 (19)	0.61140 (18)	0.0542 (7)
H21	−0.0868	0.2114	0.6466	0.065*
C22	0.0553 (3)	0.13137 (17)	0.57289 (17)	0.0464 (6)
H22	−0.0151	0.0915	0.5824	0.056*
C25	0.2933 (3)	−0.02809 (17)	0.70083 (16)	0.0502 (7)
H251	0.2101	0.0249	0.7018	0.060*
H252	0.3776	−0.0073	0.6510	0.060*
C26	0.3500 (3)	−0.06977 (19)	0.79062 (17)	0.0575 (8)
H261	0.3441	−0.0215	0.8179	0.069*
H262	0.4565	−0.1025	0.7832	0.069*
C27	0.2377 (4)	−0.1378 (2)	0.84733 (17)	0.0616 (8)
H271	0.2794	−0.1843	0.8990	0.074*
H272	0.1375	−0.1048	0.8690	0.074*
C28	0.2244 (4)	−0.1824 (2)	0.78017 (17)	0.0687 (9)
H281	0.3079	−0.2351	0.7782	0.082*
H282	0.1251	−0.2046	0.7959	0.082*
C30	−0.2721 (3)	0.44162 (18)	1.08795 (17)	0.0534 (7)
H30	−0.2631	0.3836	1.1335	0.064*
C31	−0.2150 (3)	0.45403 (17)	0.99830 (17)	0.0468 (7)
C32	−0.2535 (3)	0.55481 (16)	0.95198 (16)	0.0430 (6)
C33	−0.2305 (3)	0.62018 (17)	0.86288 (17)	0.0458 (6)
C35	−0.3802 (3)	0.73629 (19)	0.92152 (19)	0.0600 (8)
H35	−0.4276	0.7991	0.9088	0.072*
C37	−0.3365 (3)	0.59490 (17)	1.02000 (16)	0.0446 (6)
C38	−0.4294 (3)	0.53417 (18)	1.18981 (16)	0.0468 (7)
C39	−0.4229 (4)	0.60878 (19)	1.21646 (18)	0.0626 (8)
H39	−0.3627	0.6546	1.1787	0.075*
C40	−0.5069 (4)	0.6149 (2)	1.3000 (2)	0.0719 (9)
H40	−0.5041	0.6664	1.3170	0.086*
C41	−0.5943 (4)	0.5476 (2)	1.35894 (19)	0.0617 (8)
C42	−0.5965 (3)	0.4730 (2)	1.33070 (19)	0.0637 (8)
H42	−0.6538	0.4260	1.3693	0.076*
C43	−0.5163 (3)	0.4657 (2)	1.24665 (17)	0.0552 (7)
H43	−0.5211	0.4151	1.2289	0.066*
C44	−0.6872 (4)	0.5557 (3)	1.4501 (2)	0.0919 (11)
H441	−0.7890	0.5402	1.4592	0.138*
H442	−0.6971	0.6191	1.4506	0.138*
H443	−0.6342	0.5130	1.4981	0.138*
C45	−0.1389 (3)	0.37392 (16)	0.96308 (16)	0.0426 (6)
C46	−0.0005 (3)	0.32038 (18)	0.98691 (17)	0.0496 (7)
H46	0.0462	0.3350	1.0251	0.060*
C47	0.0700 (3)	0.24517 (19)	0.95481 (19)	0.0592 (8)
H47	0.1640	0.2099	0.9708	0.071*
C48	0.0001 (4)	0.22310 (19)	0.89926 (19)	0.0562 (7)
C49	−0.1395 (4)	0.27394 (19)	0.87578 (18)	0.0563 (7)
H49	−0.1871	0.2581	0.8388	0.068*
C50	−0.2080 (3)	0.34898 (18)	0.90797 (17)	0.0508 (7)
H50	−0.3026	0.3836	0.8924	0.061*
C53	−0.0106 (3)	0.52431 (18)	0.78628 (17)	0.0521 (7)
H531	−0.0438	0.4688	0.7858	0.062*
H532	0.0390	0.5077	0.8386	0.062*
C54	0.0984 (3)	0.56544 (19)	0.69815 (17)	0.0571 (7)
H541	0.1655	0.6014	0.7071	0.069*
H542	0.1625	0.5163	0.6742	0.069*
C55	−0.0132 (3)	0.62861 (19)	0.63545 (17)	0.0574 (7)
H551	−0.0603	0.5922	0.6133	0.069*
H552	0.0386	0.6746	0.5840	0.069*
C56	−0.1328 (3)	0.67548 (19)	0.69846 (16)	0.0576 (8)
H561	−0.0987	0.7299	0.7008	0.069*
H562	−0.2330	0.6952	0.6789	0.069*
Cl23	0.06434 (12)	0.35242 (6)	0.64549 (6)	0.0915 (3)
Cl51	0.08881 (13)	0.12936 (6)	0.85807 (7)	0.1017 (4)
N1	0.3089 (2)	−0.03272 (14)	0.37193 (13)	0.0444 (5)
N6	0.2761 (3)	−0.22063 (15)	0.62491 (14)	0.0556 (6)
N8	0.3286 (2)	−0.19553 (14)	0.46364 (14)	0.0461 (5)
N24	0.2366 (3)	−0.10608 (14)	0.69211 (13)	0.0507 (6)
N29	−0.3456 (2)	0.52587 (14)	1.10356 (13)	0.0497 (6)
N34	−0.3012 (3)	0.71100 (15)	0.84872 (15)	0.0586 (6)
N36	−0.4013 (3)	0.68604 (15)	1.00855 (14)	0.0519 (6)
N52	−0.1417 (3)	0.60092 (14)	0.78740 (13)	0.0492 (6)

	U11	U22	U33	U12	U13	U23
C2	0.0559 (17)	0.0360 (14)	0.0417 (16)	−0.0042 (12)	−0.0103 (13)	−0.0080 (12)
C3	0.0426 (15)	0.0390 (14)	0.0401 (15)	−0.0051 (12)	−0.0104 (12)	−0.0096 (12)
C4	0.0412 (15)	0.0386 (14)	0.0401 (14)	−0.0090 (11)	−0.0088 (11)	−0.0111 (12)
C5	0.0488 (17)	0.0395 (15)	0.0428 (15)	−0.0103 (12)	−0.0073 (12)	−0.0085 (12)
C7	0.070 (2)	0.0363 (15)	0.0526 (18)	−0.0150 (14)	−0.0114 (15)	−0.0106 (14)
C9	0.0386 (15)	0.0399 (15)	0.0418 (15)	−0.0072 (12)	−0.0102 (12)	−0.0105 (12)
C10	0.0522 (17)	0.0433 (15)	0.0341 (14)	−0.0117 (13)	−0.0034 (12)	−0.0099 (12)
C11	0.068 (2)	0.0485 (17)	0.0490 (17)	−0.0010 (15)	−0.0079 (15)	−0.0168 (14)
C12	0.089 (2)	0.0490 (18)	0.0499 (18)	−0.0106 (17)	0.0008 (17)	−0.0198 (15)
C13	0.079 (2)	0.0597 (19)	0.0394 (16)	−0.0269 (17)	0.0012 (15)	−0.0146 (15)
C14	0.075 (2)	0.080 (2)	0.0440 (17)	−0.0086 (18)	−0.0185 (15)	−0.0135 (16)
C15	0.0596 (19)	0.0644 (19)	0.0436 (16)	−0.0016 (15)	−0.0096 (14)	−0.0161 (14)
C16	0.131 (3)	0.093 (3)	0.0460 (18)	−0.041 (2)	−0.0030 (19)	−0.0286 (17)
C17	0.0438 (16)	0.0337 (13)	0.0340 (13)	−0.0030 (12)	−0.0123 (12)	−0.0044 (11)
C18	0.0463 (16)	0.0452 (15)	0.0438 (15)	−0.0098 (13)	−0.0031 (12)	−0.0094 (12)
C19	0.070 (2)	0.0444 (16)	0.0549 (17)	−0.0174 (15)	−0.0123 (16)	−0.0162 (14)
C20	0.068 (2)	0.0459 (16)	0.0412 (15)	−0.0020 (15)	−0.0100 (14)	−0.0153 (13)
C21	0.0524 (18)	0.0537 (17)	0.0496 (16)	0.0007 (15)	−0.0036 (14)	−0.0178 (14)
C22	0.0432 (16)	0.0434 (15)	0.0500 (16)	−0.0067 (12)	−0.0097 (13)	−0.0108 (13)
C25	0.0644 (19)	0.0439 (15)	0.0422 (15)	−0.0078 (13)	−0.0169 (13)	−0.0092 (12)
C26	0.072 (2)	0.0575 (17)	0.0426 (16)	−0.0152 (15)	−0.0180 (14)	−0.0070 (14)
C27	0.073 (2)	0.0655 (19)	0.0402 (16)	−0.0132 (16)	−0.0077 (15)	−0.0105 (14)
C28	0.104 (3)	0.0559 (18)	0.0418 (17)	−0.0307 (18)	−0.0082 (16)	−0.0021 (14)
C30	0.0649 (19)	0.0356 (15)	0.0475 (17)	−0.0055 (13)	−0.0038 (14)	−0.0043 (12)
C31	0.0496 (17)	0.0414 (15)	0.0419 (15)	−0.0075 (13)	−0.0030 (13)	−0.0074 (12)
C32	0.0404 (15)	0.0388 (14)	0.0436 (15)	−0.0018 (12)	−0.0061 (12)	−0.0096 (12)
C33	0.0493 (17)	0.0409 (15)	0.0430 (15)	−0.0017 (13)	−0.0141 (13)	−0.0081 (12)
C35	0.064 (2)	0.0447 (17)	0.0566 (19)	0.0113 (14)	−0.0131 (15)	−0.0095 (15)
C37	0.0409 (15)	0.0409 (15)	0.0438 (15)	−0.0028 (12)	−0.0064 (12)	−0.0068 (13)
C38	0.0500 (17)	0.0459 (16)	0.0360 (14)	0.0002 (13)	−0.0080 (13)	−0.0077 (12)
C39	0.085 (2)	0.0423 (16)	0.0510 (18)	−0.0099 (15)	−0.0010 (16)	−0.0106 (14)
C40	0.100 (3)	0.0532 (19)	0.061 (2)	−0.0037 (18)	−0.0095 (19)	−0.0247 (16)
C41	0.067 (2)	0.0632 (19)	0.0464 (17)	−0.0006 (16)	−0.0076 (15)	−0.0155 (15)
C42	0.063 (2)	0.074 (2)	0.0491 (18)	−0.0220 (17)	−0.0028 (15)	−0.0123 (16)
C43	0.0632 (19)	0.0609 (18)	0.0430 (16)	−0.0175 (15)	−0.0051 (14)	−0.0165 (14)
C44	0.103 (3)	0.106 (3)	0.058 (2)	0.001 (2)	−0.0004 (19)	−0.036 (2)
C45	0.0447 (16)	0.0350 (14)	0.0409 (14)	−0.0081 (12)	−0.0021 (12)	−0.0060 (11)
C46	0.0507 (17)	0.0481 (16)	0.0495 (16)	−0.0067 (14)	−0.0093 (13)	−0.0153 (13)
C47	0.0533 (18)	0.0490 (17)	0.0660 (19)	0.0018 (14)	−0.0098 (15)	−0.0140 (15)
C48	0.067 (2)	0.0441 (16)	0.0557 (17)	−0.0085 (15)	−0.0030 (15)	−0.0188 (14)
C49	0.069 (2)	0.0515 (17)	0.0519 (17)	−0.0158 (16)	−0.0115 (15)	−0.0165 (14)
C50	0.0498 (17)	0.0469 (16)	0.0502 (16)	−0.0064 (13)	−0.0124 (13)	−0.0073 (13)
C53	0.0548 (18)	0.0440 (15)	0.0471 (16)	−0.0037 (13)	−0.0021 (13)	−0.0097 (13)
C54	0.0581 (19)	0.0569 (17)	0.0463 (16)	−0.0085 (14)	−0.0030 (14)	−0.0090 (14)
C55	0.0619 (19)	0.0650 (19)	0.0410 (15)	−0.0142 (15)	−0.0069 (14)	−0.0107 (14)
C56	0.070 (2)	0.0535 (17)	0.0388 (15)	−0.0017 (15)	−0.0145 (14)	−0.0039 (13)
Cl23	0.1234 (8)	0.0718 (6)	0.0892 (6)	−0.0090 (5)	−0.0045 (6)	−0.0513 (5)
Cl51	0.1162 (8)	0.0781 (6)	0.1212 (8)	0.0104 (6)	−0.0169 (6)	−0.0636 (6)
N1	0.0531 (14)	0.0415 (12)	0.0384 (12)	−0.0056 (10)	−0.0099 (10)	−0.0124 (10)
N6	0.0789 (17)	0.0413 (13)	0.0460 (14)	−0.0189 (12)	−0.0083 (12)	−0.0091 (11)
N8	0.0534 (14)	0.0403 (12)	0.0467 (13)	−0.0121 (10)	−0.0101 (11)	−0.0126 (11)
N24	0.0726 (16)	0.0429 (13)	0.0360 (12)	−0.0179 (11)	−0.0061 (11)	−0.0087 (10)
N29	0.0565 (15)	0.0397 (12)	0.0412 (13)	−0.0012 (11)	−0.0010 (11)	−0.0083 (10)
N34	0.0714 (17)	0.0448 (14)	0.0460 (13)	0.0102 (12)	−0.0124 (12)	−0.0089 (11)
N36	0.0546 (15)	0.0433 (13)	0.0450 (14)	0.0066 (11)	−0.0098 (11)	−0.0075 (11)
N52	0.0589 (15)	0.0413 (12)	0.0367 (12)	0.0006 (11)	−0.0073 (11)	−0.0061 (10)

C2—C3	1.363 (3)	C30—C31	1.355 (3)
C2—N1	1.387 (3)	C30—N29	1.387 (3)
C2—H2	0.9300	C30—H30	0.9300
C3—C4	1.452 (3)	C31—C32	1.459 (3)
C3—C17	1.483 (3)	C31—C45	1.485 (3)
C4—C9	1.407 (3)	C32—C37	1.404 (3)
C4—C5	1.421 (3)	C32—C33	1.418 (3)
C5—N6	1.352 (3)	C33—N34	1.355 (3)
C5—N24	1.357 (3)	C33—N52	1.357 (3)
C7—N8	1.323 (3)	C35—N36	1.318 (3)
C7—N6	1.334 (3)	C35—N34	1.337 (3)
C7—H7	0.9300	C35—H35	0.9300
C9—N8	1.347 (3)	C37—N36	1.351 (3)
C9—N1	1.375 (3)	C37—N29	1.376 (3)
C10—C15	1.375 (4)	C38—C39	1.374 (4)
C10—C11	1.376 (3)	C38—C43	1.375 (4)
C10—N1	1.429 (3)	C38—N29	1.430 (3)
C11—C12	1.379 (4)	C39—C40	1.383 (4)
C11—H11	0.9300	C39—H39	0.9300
C12—C13	1.374 (4)	C40—C41	1.375 (4)
C12—H12	0.9300	C40—H40	0.9300
C13—C14	1.374 (4)	C41—C42	1.378 (4)
C13—C16	1.512 (4)	C41—C44	1.519 (4)
C14—C15	1.389 (4)	C42—C43	1.386 (4)
C14—H14	0.9300	C42—H42	0.9300
C15—H15	0.9300	C43—H43	0.9300
C16—H161	0.9600	C44—H441	0.9600
C16—H162	0.9600	C44—H442	0.9600
C16—H163	0.9600	C44—H443	0.9600
C17—C22	1.387 (3)	C45—C46	1.377 (3)
C17—C18	1.388 (3)	C45—C50	1.387 (3)
C18—C19	1.382 (3)	C46—C47	1.385 (4)
C18—H18	0.9300	C46—H46	0.9300
C19—C20	1.370 (4)	C47—C48	1.372 (4)
C19—H19	0.9300	C47—H47	0.9300
C20—C21	1.370 (4)	C48—C49	1.374 (4)
C20—Cl23	1.742 (3)	C48—Cl51	1.737 (3)
C21—C22	1.381 (3)	C49—C50	1.380 (4)
C21—H21	0.9300	C49—H49	0.9300
C22—H22	0.9300	C50—H50	0.9300
C25—N24	1.467 (3)	C53—N52	1.458 (3)
C25—C26	1.510 (3)	C53—C54	1.520 (3)
C25—H251	0.9700	C53—H531	0.9700
C25—H252	0.9700	C53—H532	0.9700
C26—C27	1.514 (4)	C54—C55	1.516 (4)
C26—H261	0.9700	C54—H541	0.9700
C26—H262	0.9700	C54—H542	0.9700
C27—C28	1.503 (4)	C55—C56	1.517 (4)
C27—H271	0.9700	C55—H551	0.9700
C27—H272	0.9700	C55—H552	0.9700
C28—N24	1.475 (3)	C56—N52	1.472 (3)
C28—H281	0.9700	C56—H561	0.9700
C28—H282	0.9700	C56—H562	0.9700
C3—C2—N1	111.1 (2)	C33—C32—C31	139.3 (2)
C3—C2—H2	124.5	N34—C33—N52	114.8 (2)
N1—C2—H2	124.5	N34—C33—C32	119.2 (2)
C2—C3—C4	106.1 (2)	N52—C33—C32	126.0 (2)
C2—C3—C17	123.5 (2)	N36—C35—N34	130.0 (2)
C4—C3—C17	130.3 (2)	N36—C35—H35	115.0
C9—C4—C5	114.5 (2)	N34—C35—H35	115.0
C9—C4—C3	106.3 (2)	N36—C37—N29	123.3 (2)
C5—C4—C3	139.1 (2)	N36—C37—C32	127.2 (2)
N6—C5—N24	115.3 (2)	N29—C37—C32	109.4 (2)
N6—C5—C4	119.1 (2)	C39—C38—C43	120.1 (2)
N24—C5—C4	125.6 (2)	C39—C38—N29	120.9 (2)
N8—C7—N6	129.5 (2)	C43—C38—N29	119.0 (2)
N8—C7—H7	115.3	C38—C39—C40	119.2 (3)
N6—C7—H7	115.3	C38—C39—H39	120.4
N8—C9—N1	123.6 (2)	C40—C39—H39	120.4
N8—C9—C4	127.2 (2)	C41—C40—C39	122.4 (3)
N1—C9—C4	109.1 (2)	C41—C40—H40	118.8
C15—C10—C11	119.3 (2)	C39—C40—H40	118.8
C15—C10—N1	119.6 (2)	C40—C41—C42	116.9 (3)
C11—C10—N1	121.0 (2)	C40—C41—C44	121.8 (3)
C10—C11—C12	120.0 (3)	C42—C41—C44	121.3 (3)
C10—C11—H11	120.0	C41—C42—C43	122.2 (3)
C12—C11—H11	120.0	C41—C42—H42	118.9
C13—C12—C11	121.9 (3)	C43—C42—H42	118.9
C13—C12—H12	119.1	C38—C43—C42	119.2 (3)
C11—C12—H12	119.1	C38—C43—H43	120.4
C14—C13—C12	117.4 (3)	C42—C43—H43	120.4
C14—C13—C16	121.1 (3)	C41—C44—H441	109.5
C12—C13—C16	121.5 (3)	C41—C44—H442	109.5
C13—C14—C15	121.8 (3)	H441—C44—H442	109.5
C13—C14—H14	119.1	C41—C44—H443	109.5
C15—C14—H14	119.1	H441—C44—H443	109.5
C10—C15—C14	119.6 (3)	H442—C44—H443	109.5
C10—C15—H15	120.2	C46—C45—C50	118.2 (2)
C14—C15—H15	120.2	C46—C45—C31	120.8 (2)
C13—C16—H161	109.5	C50—C45—C31	120.9 (2)
C13—C16—H162	109.5	C45—C46—C47	121.0 (3)
H161—C16—H162	109.5	C45—C46—H46	119.5
C13—C16—H163	109.5	C47—C46—H46	119.5
H161—C16—H163	109.5	C48—C47—C46	119.5 (3)
H162—C16—H163	109.5	C48—C47—H47	120.3
C22—C17—C18	118.0 (2)	C46—C47—H47	120.3
C22—C17—C3	120.9 (2)	C47—C48—C49	121.0 (3)
C18—C17—C3	121.0 (2)	C47—C48—Cl51	119.7 (2)
C19—C18—C17	120.8 (2)	C49—C48—Cl51	119.3 (2)
C19—C18—H18	119.6	C48—C49—C50	118.9 (3)
C17—C18—H18	119.6	C48—C49—H49	120.6
C20—C19—C18	119.6 (3)	C50—C49—H49	120.6
C20—C19—H19	120.2	C49—C50—C45	121.5 (3)
C18—C19—H19	120.2	C49—C50—H50	119.3
C21—C20—C19	121.1 (3)	C45—C50—H50	119.3
C21—C20—Cl23	120.0 (2)	N52—C53—C54	103.2 (2)
C19—C20—Cl23	118.9 (2)	N52—C53—H531	111.1
C20—C21—C22	119.1 (3)	C54—C53—H531	111.1
C20—C21—H21	120.5	N52—C53—H532	111.1
C22—C21—H21	120.5	C54—C53—H532	111.1
C21—C22—C17	121.4 (3)	H531—C53—H532	109.1
C21—C22—H22	119.3	C55—C54—C53	102.9 (2)
C17—C22—H22	119.3	C55—C54—H541	111.2
N24—C25—C26	103.9 (2)	C53—C54—H541	111.2
N24—C25—H251	111.0	C55—C54—H542	111.2
C26—C25—H251	111.0	C53—C54—H542	111.2
N24—C25—H252	111.0	H541—C54—H542	109.1
C26—C25—H252	111.0	C54—C55—C56	101.6 (2)
H251—C25—H252	109.0	C54—C55—H551	111.5
C25—C26—C27	102.6 (2)	C56—C55—H551	111.5
C25—C26—H261	111.2	C54—C55—H552	111.5
C27—C26—H261	111.2	C56—C55—H552	111.5
C25—C26—H262	111.2	H551—C55—H552	109.3
C27—C26—H262	111.2	N52—C56—C55	103.4 (2)
H261—C26—H262	109.2	N52—C56—H561	111.1
C28—C27—C26	102.1 (2)	C55—C56—H561	111.1
C28—C27—H271	111.4	N52—C56—H562	111.1
C26—C27—H271	111.4	C55—C56—H562	111.1
C28—C27—H272	111.4	H561—C56—H562	109.0
C26—C27—H272	111.4	C9—N1—C2	107.42 (19)
H271—C27—H272	109.2	C9—N1—C10	126.5 (2)
N24—C28—C27	104.3 (2)	C2—N1—C10	125.3 (2)
N24—C28—H281	110.9	C7—N6—C5	118.3 (2)
C27—C28—H281	110.9	C7—N8—C9	111.1 (2)
N24—C28—H282	110.9	C5—N24—C25	124.8 (2)
C27—C28—H282	110.9	C5—N24—C28	119.1 (2)
H281—C28—H282	108.9	C25—N24—C28	109.5 (2)
C31—C30—N29	111.8 (2)	C37—N29—C30	106.9 (2)
C31—C30—H30	124.1	C37—N29—C38	128.0 (2)
N29—C30—H30	124.1	C30—N29—C38	124.7 (2)
C30—C31—C32	105.8 (2)	C35—N34—C33	117.7 (2)
C30—C31—C45	122.3 (2)	C35—N36—C37	110.8 (2)
C32—C31—C45	131.8 (2)	C33—N52—C53	125.8 (2)
C37—C32—C33	114.6 (2)	C33—N52—C56	119.9 (2)
C37—C32—C31	106.1 (2)	C53—N52—C56	110.9 (2)
N1—C2—C3—C4	−0.2 (3)	C30—C31—C45—C46	−65.2 (4)
N1—C2—C3—C17	−177.8 (2)	C32—C31—C45—C46	118.8 (3)
C2—C3—C4—C9	−0.2 (3)	C30—C31—C45—C50	112.5 (3)
C17—C3—C4—C9	177.2 (2)	C32—C31—C45—C50	−63.5 (4)
C2—C3—C4—C5	−177.6 (3)	C50—C45—C46—C47	1.7 (4)
C17—C3—C4—C5	−0.2 (5)	C31—C45—C46—C47	179.5 (2)
C9—C4—C5—N6	−4.5 (3)	C45—C46—C47—C48	−0.7 (4)
C3—C4—C5—N6	172.7 (3)	C46—C47—C48—C49	−0.6 (4)
C9—C4—C5—N24	176.0 (2)	C46—C47—C48—Cl51	179.5 (2)
C3—C4—C5—N24	−6.8 (5)	C47—C48—C49—C50	1.0 (4)
C5—C4—C9—N8	1.9 (4)	Cl51—C48—C49—C50	−179.2 (2)
C3—C4—C9—N8	−176.2 (2)	C48—C49—C50—C45	0.1 (4)
C5—C4—C9—N1	178.7 (2)	C46—C45—C50—C49	−1.4 (4)
C3—C4—C9—N1	0.6 (3)	C31—C45—C50—C49	−179.1 (2)
C15—C10—C11—C12	−0.6 (4)	N52—C53—C54—C55	−33.6 (3)
N1—C10—C11—C12	179.3 (2)	C53—C54—C55—C56	42.5 (3)
C10—C11—C12—C13	1.0 (4)	C54—C55—C56—N52	−34.9 (3)
C11—C12—C13—C14	−0.5 (4)	N8—C9—N1—C2	176.2 (2)
C11—C12—C13—C16	179.8 (3)	C4—C9—N1—C2	−0.7 (3)
C12—C13—C14—C15	−0.4 (4)	N8—C9—N1—C10	6.1 (4)
C16—C13—C14—C15	179.3 (3)	C4—C9—N1—C10	−170.8 (2)
C11—C10—C15—C14	−0.3 (4)	C3—C2—N1—C9	0.6 (3)
N1—C10—C15—C14	179.8 (2)	C3—C2—N1—C10	170.8 (2)
C13—C14—C15—C10	0.8 (5)	C15—C10—N1—C9	131.9 (3)
C2—C3—C17—C22	112.0 (3)	C11—C10—N1—C9	−48.0 (4)
C4—C3—C17—C22	−65.1 (4)	C15—C10—N1—C2	−36.5 (4)
C2—C3—C17—C18	−67.7 (3)	C11—C10—N1—C2	143.6 (3)
C4—C3—C17—C18	115.2 (3)	N8—C7—N6—C5	−1.2 (4)
C22—C17—C18—C19	1.7 (4)	N24—C5—N6—C7	−176.2 (2)
C3—C17—C18—C19	−178.6 (2)	C4—C5—N6—C7	4.3 (4)
C17—C18—C19—C20	−1.2 (4)	N6—C7—N8—C9	−1.5 (4)
C18—C19—C20—C21	0.2 (4)	N1—C9—N8—C7	−175.4 (2)
C18—C19—C20—Cl23	179.88 (19)	C4—C9—N8—C7	0.9 (4)
C19—C20—C21—C22	0.3 (4)	N6—C5—N24—C25	146.9 (2)
Cl23—C20—C21—C22	−179.42 (19)	C4—C5—N24—C25	−33.6 (4)
C20—C21—C22—C17	0.3 (4)	N6—C5—N24—C28	−1.6 (4)
C18—C17—C22—C21	−1.2 (4)	C4—C5—N24—C28	177.9 (3)
C3—C17—C22—C21	179.1 (2)	C26—C25—N24—C5	−138.3 (3)
N24—C25—C26—C27	−33.8 (3)	C26—C25—N24—C28	12.8 (3)
C25—C26—C27—C28	42.1 (3)	C27—C28—N24—C5	166.5 (2)
C26—C27—C28—N24	−34.2 (3)	C27—C28—N24—C25	13.6 (3)
N29—C30—C31—C32	0.5 (3)	N36—C37—N29—C30	177.5 (2)
N29—C30—C31—C45	−176.5 (2)	C32—C37—N29—C30	−1.7 (3)
C30—C31—C32—C37	−1.4 (3)	N36—C37—N29—C38	4.5 (4)
C45—C31—C32—C37	175.1 (3)	C32—C37—N29—C38	−174.7 (2)
C30—C31—C32—C33	177.5 (3)	C31—C30—N29—C37	0.7 (3)
C45—C31—C32—C33	−5.9 (5)	C31—C30—N29—C38	174.0 (2)
C37—C32—C33—N34	−6.7 (4)	C39—C38—N29—C37	−45.6 (4)
C31—C32—C33—N34	174.3 (3)	C43—C38—N29—C37	135.0 (3)
C37—C32—C33—N52	173.1 (2)	C39—C38—N29—C30	142.5 (3)
C31—C32—C33—N52	−5.8 (5)	C43—C38—N29—C30	−36.9 (4)
C33—C32—C37—N36	3.6 (4)	N36—C35—N34—C33	0.5 (5)
C31—C32—C37—N36	−177.2 (2)	N52—C33—N34—C35	−174.7 (3)
C33—C32—C37—N29	−177.4 (2)	C32—C33—N34—C35	5.1 (4)
C31—C32—C37—N29	1.9 (3)	N34—C35—N36—C37	−3.7 (4)
C43—C38—C39—C40	−1.2 (4)	N29—C37—N36—C35	−177.6 (3)
N29—C38—C39—C40	179.4 (3)	C32—C37—N36—C35	1.3 (4)
C38—C39—C40—C41	1.6 (5)	N34—C33—N52—C53	155.2 (2)
C39—C40—C41—C42	−0.7 (5)	C32—C33—N52—C53	−24.7 (4)
C39—C40—C41—C44	−179.4 (3)	N34—C33—N52—C56	−2.2 (4)
C40—C41—C42—C43	−0.6 (5)	C32—C33—N52—C56	177.9 (3)
C44—C41—C42—C43	178.1 (3)	C54—C53—N52—C33	−147.2 (3)
C39—C38—C43—C42	0.0 (4)	C54—C53—N52—C56	11.9 (3)
N29—C38—C43—C42	179.4 (2)	C55—C56—N52—C33	175.1 (2)
C41—C42—C43—C38	1.0 (4)	C55—C56—N52—C53	14.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1i	0.93	2.68	3.483 (3)	144
C46—H46···Cg2ii	0.93	2.73	3.549 (3)	147
C25—H251···Cg3	0.97	2.79	3.462 (3)	127
C53—H531···Cg4	0.97	2.84	3.506 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N6/C5/C4/C9/N8/C7, N34/C33/C32/C37/N36/C35, C17–C22 and C45–C50 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1i	0.93	2.68	3.483 (3)	144
C46—H46⋯Cg2ii	0.93	2.73	3.549 (3)	147
C25—H251⋯Cg3	0.97	2.79	3.462 (3)	127
C53—H531⋯Cg4	0.97	2.84	3.506 (3)	127

Symmetry codes: (i) ; (ii) .