2-Chloro-6,6-dimethyl-5,6-dihydro-indazolo[2,3-c]quinazoline.

Two independent but virtually identical mol-ecules comprise the asymmetric unit of the title compound, C(16)H(14)ClN(3). The mol-ecules have a slightly curved shape owing to puckering in the six-membered C(4)N(2) ring; the respective dihedral angles formed between the benzene rings are 12.64 (7) and 11.72 (7)°. In the crystal, layers sustained by a combination of N-H⋯N hydrogen bonding as well as C-H⋯N and C-H⋯π contacts are formed; these stack along [011] and are connected by further C-H⋯π contacts.

Related literature

For background to the synthesis and biological activity of the title compound, see: Rousselet et al. (1993 ▶); Ferreira et al. (2007 ▶). For additional geometric analysis, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H14ClN3

M = 283.75

Triclinic,

a = 9.8636 (2) Å

b = 10.7971 (2) Å

c = 13.2387 (3) Å

α = 93.483 (1)°

β = 100.391 (1)°

γ = 104.419 (1)°

V = 1334.81 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 120 K

0.55 × 0.25 × 0.15 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.885, T max = 1.000

27218 measured reflections

6102 independent reflections

5108 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.02

6102 reflections

371 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003818/hb5323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003818/hb5323Isup2.hkl

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

C16H14ClN3	Z = 4
Mr = 283.75	F(000) = 592
Triclinic, P1	Dx = 1.412 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8636 (2) Å	Cell parameters from 5954 reflections
b = 10.7971 (2) Å	θ = 2.9–27.5°
c = 13.2387 (3) Å	µ = 0.28 mm−1
α = 93.483 (1)°	T = 120 K
β = 100.391 (1)°	Block, pale-yellow
γ = 104.419 (1)°	0.55 × 0.25 × 0.15 mm
V = 1334.81 (5) Å3

Nonius KappaCCD area-detector diffractometer	6102 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	5108 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.037
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −14→14
Tmin = 0.885, Tmax = 1.000	l = −17→17
27218 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.5871P] where P = (Fo2 + 2Fc2)/3
6102 reflections	(Δ/σ)max = 0.001
371 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.33159 (4)	−0.34794 (3)	0.46107 (3)	0.02533 (10)
N1	0.47189 (12)	0.14829 (11)	0.28749 (9)	0.0170 (2)
H1N	0.5189 (18)	0.1492 (16)	0.2355 (13)	0.020*
N2	0.30560 (12)	0.22108 (10)	0.36420 (8)	0.0146 (2)
N3	0.25126 (12)	0.31785 (11)	0.39366 (9)	0.0166 (2)
C1	0.37097 (15)	−0.20111 (13)	0.41036 (10)	0.0178 (3)
C2	0.46556 (15)	−0.18303 (13)	0.34342 (11)	0.0191 (3)
H2	0.5094	−0.2488	0.3275	0.023*
C3	0.49562 (14)	−0.06863 (13)	0.30000 (11)	0.0180 (3)
H3	0.5592	−0.0565	0.2532	0.022*
C4	0.43335 (14)	0.02947 (13)	0.32429 (10)	0.0153 (3)
C5	0.33861 (14)	0.01066 (13)	0.39313 (10)	0.0149 (3)
C6	0.30674 (14)	−0.10637 (13)	0.43533 (10)	0.0166 (3)
H6	0.2415	−0.1207	0.4808	0.020*
C7	0.37046 (14)	0.22740 (13)	0.27162 (10)	0.0160 (3)
C8	0.45339 (16)	0.36485 (14)	0.26594 (12)	0.0215 (3)
H8A	0.5234	0.3969	0.3306	0.032*
H8B	0.3871	0.4193	0.2555	0.032*
H8C	0.5032	0.3670	0.2081	0.032*
C9	0.25205 (16)	0.17480 (15)	0.17637 (11)	0.0231 (3)
H9A	0.2939	0.1762	0.1146	0.035*
H9B	0.1845	0.2282	0.1703	0.035*
H9C	0.2017	0.0862	0.1831	0.035*
C10	0.28291 (14)	0.11864 (13)	0.41894 (10)	0.0148 (3)
C11	0.20930 (14)	0.15069 (13)	0.49425 (10)	0.0150 (3)
C12	0.15553 (15)	0.09112 (13)	0.57641 (10)	0.0177 (3)
H12	0.1643	0.0077	0.5897	0.021*
C13	0.09056 (15)	0.15635 (14)	0.63631 (11)	0.0211 (3)
H13	0.0535	0.1171	0.6915	0.025*
C14	0.07742 (16)	0.28172 (14)	0.61761 (11)	0.0219 (3)
H14	0.0322	0.3245	0.6608	0.026*
C15	0.12848 (15)	0.34197 (13)	0.53880 (11)	0.0194 (3)
H15	0.1199	0.4259	0.5271	0.023*
C16	0.19440 (14)	0.27539 (13)	0.47525 (10)	0.0160 (3)
Cl2	1.01515 (4)	0.86179 (3)	0.04959 (3)	0.02812 (11)
N4	1.01094 (12)	0.36108 (11)	0.20762 (9)	0.0162 (2)
H4N	1.0824 (18)	0.3620 (16)	0.2564 (13)	0.019*
N5	0.76776 (12)	0.28013 (10)	0.13350 (8)	0.0147 (2)
N6	0.64868 (12)	0.18074 (11)	0.10529 (9)	0.0159 (2)
C17	1.01399 (15)	0.71382 (13)	0.09521 (11)	0.0182 (3)
C18	1.13622 (15)	0.69989 (13)	0.15913 (11)	0.0186 (3)
H18	1.2199	0.7697	0.1762	0.022*
C19	1.13493 (14)	0.58330 (13)	0.19782 (10)	0.0171 (3)
H19	1.2183	0.5733	0.2415	0.020*
C20	1.01243 (14)	0.48057 (13)	0.17320 (10)	0.0146 (3)
C21	0.88979 (14)	0.49500 (12)	0.10646 (10)	0.0143 (3)
C22	0.89169 (15)	0.61293 (13)	0.06827 (10)	0.0166 (3)
H22	0.8093	0.6239	0.0240	0.020*
C23	0.87707 (14)	0.27850 (13)	0.22571 (10)	0.0157 (3)
C24	0.89323 (16)	0.14258 (13)	0.23258 (12)	0.0209 (3)
H24A	0.9129	0.1102	0.1675	0.031*
H24B	0.8047	0.0865	0.2453	0.031*
H24C	0.9725	0.1435	0.2894	0.031*
C25	0.83271 (15)	0.33020 (15)	0.32098 (11)	0.0215 (3)
H25A	0.9060	0.3329	0.3824	0.032*
H25B	0.7414	0.2738	0.3288	0.032*
H25C	0.8222	0.4172	0.3129	0.032*
C26	0.76750 (14)	0.38327 (12)	0.08024 (10)	0.0142 (3)
C27	0.63765 (14)	0.34888 (12)	0.00739 (10)	0.0146 (3)
C28	0.57034 (15)	0.40825 (13)	−0.07201 (10)	0.0174 (3)
H28	0.6155	0.4920	−0.0863	0.021*
C29	0.43847 (15)	0.34197 (14)	−0.12786 (11)	0.0200 (3)
H29	0.3911	0.3813	−0.1806	0.024*
C30	0.37114 (15)	0.21577 (14)	−0.10858 (11)	0.0201 (3)
H30	0.2795	0.1727	−0.1486	0.024*
C31	0.43480 (15)	0.15426 (13)	−0.03367 (10)	0.0175 (3)
H31	0.3900	0.0690	−0.0225	0.021*
C32	0.56925 (14)	0.22232 (13)	0.02623 (10)	0.0155 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0402 (2)	0.01712 (17)	0.02142 (18)	0.01136 (15)	0.00696 (15)	0.00566 (13)
N1	0.0154 (6)	0.0180 (6)	0.0202 (6)	0.0058 (5)	0.0075 (5)	0.0043 (5)
N2	0.0157 (5)	0.0143 (5)	0.0144 (5)	0.0050 (4)	0.0034 (4)	0.0015 (4)
N3	0.0191 (6)	0.0153 (6)	0.0165 (6)	0.0068 (5)	0.0041 (5)	0.0004 (4)
C1	0.0207 (7)	0.0149 (6)	0.0161 (6)	0.0053 (5)	−0.0011 (5)	0.0010 (5)
C2	0.0188 (7)	0.0192 (7)	0.0193 (7)	0.0090 (5)	−0.0001 (5)	−0.0019 (5)
C3	0.0149 (6)	0.0208 (7)	0.0183 (7)	0.0049 (5)	0.0041 (5)	−0.0006 (5)
C4	0.0130 (6)	0.0163 (6)	0.0150 (6)	0.0027 (5)	0.0007 (5)	0.0008 (5)
C5	0.0143 (6)	0.0156 (6)	0.0146 (6)	0.0053 (5)	0.0012 (5)	0.0005 (5)
C6	0.0172 (6)	0.0181 (7)	0.0145 (6)	0.0050 (5)	0.0022 (5)	0.0020 (5)
C7	0.0161 (6)	0.0191 (7)	0.0146 (6)	0.0060 (5)	0.0049 (5)	0.0036 (5)
C8	0.0244 (7)	0.0202 (7)	0.0233 (7)	0.0074 (6)	0.0093 (6)	0.0092 (6)
C9	0.0197 (7)	0.0350 (8)	0.0152 (7)	0.0100 (6)	0.0023 (6)	−0.0010 (6)
C10	0.0132 (6)	0.0155 (6)	0.0150 (6)	0.0031 (5)	0.0016 (5)	0.0022 (5)
C11	0.0129 (6)	0.0169 (6)	0.0144 (6)	0.0042 (5)	0.0009 (5)	0.0006 (5)
C12	0.0176 (7)	0.0190 (7)	0.0168 (7)	0.0052 (5)	0.0032 (5)	0.0040 (5)
C13	0.0199 (7)	0.0276 (8)	0.0161 (7)	0.0052 (6)	0.0055 (5)	0.0038 (6)
C14	0.0223 (7)	0.0258 (8)	0.0189 (7)	0.0093 (6)	0.0054 (6)	−0.0033 (6)
C15	0.0229 (7)	0.0175 (7)	0.0186 (7)	0.0085 (6)	0.0030 (6)	−0.0015 (5)
C16	0.0148 (6)	0.0170 (7)	0.0149 (6)	0.0040 (5)	0.0002 (5)	0.0005 (5)
Cl2	0.0325 (2)	0.01460 (17)	0.0300 (2)	−0.00067 (14)	−0.00427 (16)	0.00690 (14)
N4	0.0123 (5)	0.0167 (6)	0.0195 (6)	0.0039 (4)	0.0018 (5)	0.0055 (5)
N5	0.0147 (5)	0.0141 (5)	0.0146 (5)	0.0028 (4)	0.0029 (4)	0.0019 (4)
N6	0.0158 (5)	0.0138 (5)	0.0163 (6)	0.0007 (4)	0.0030 (4)	0.0004 (4)
C17	0.0221 (7)	0.0139 (6)	0.0180 (7)	0.0032 (5)	0.0044 (5)	0.0026 (5)
C18	0.0163 (7)	0.0179 (7)	0.0190 (7)	0.0001 (5)	0.0033 (5)	−0.0002 (5)
C19	0.0146 (6)	0.0196 (7)	0.0169 (7)	0.0049 (5)	0.0026 (5)	0.0016 (5)
C20	0.0167 (6)	0.0157 (6)	0.0132 (6)	0.0063 (5)	0.0049 (5)	0.0014 (5)
C21	0.0145 (6)	0.0143 (6)	0.0137 (6)	0.0026 (5)	0.0038 (5)	0.0007 (5)
C22	0.0174 (7)	0.0173 (7)	0.0149 (6)	0.0045 (5)	0.0023 (5)	0.0022 (5)
C23	0.0143 (6)	0.0167 (6)	0.0153 (6)	0.0034 (5)	0.0017 (5)	0.0034 (5)
C24	0.0209 (7)	0.0175 (7)	0.0244 (7)	0.0050 (6)	0.0030 (6)	0.0080 (6)
C25	0.0176 (7)	0.0295 (8)	0.0157 (7)	0.0046 (6)	0.0020 (5)	0.0004 (6)
C26	0.0159 (6)	0.0143 (6)	0.0138 (6)	0.0051 (5)	0.0049 (5)	0.0024 (5)
C27	0.0146 (6)	0.0157 (6)	0.0141 (6)	0.0043 (5)	0.0044 (5)	0.0010 (5)
C28	0.0193 (7)	0.0176 (7)	0.0163 (7)	0.0060 (5)	0.0042 (5)	0.0021 (5)
C29	0.0211 (7)	0.0247 (7)	0.0150 (7)	0.0096 (6)	0.0014 (5)	0.0004 (5)
C30	0.0148 (6)	0.0242 (7)	0.0182 (7)	0.0034 (5)	−0.0001 (5)	−0.0046 (6)
C31	0.0179 (7)	0.0158 (6)	0.0167 (7)	0.0012 (5)	0.0047 (5)	−0.0033 (5)
C32	0.0169 (6)	0.0160 (6)	0.0143 (6)	0.0045 (5)	0.0052 (5)	0.0005 (5)

Cl1—C1	1.7411 (14)	Cl2—C17	1.7401 (14)
N1—C4	1.3884 (17)	N4—C20	1.3917 (17)
N1—C7	1.4649 (17)	N4—C23	1.4662 (17)
N1—H1N	0.896 (18)	N4—H4N	0.863 (17)
N2—C10	1.3532 (17)	N5—C26	1.3540 (17)
N2—N3	1.3550 (15)	N5—N6	1.3551 (15)
N2—C7	1.4791 (17)	N5—C23	1.4800 (17)
N3—C16	1.3573 (18)	N6—C32	1.3591 (17)
C1—C6	1.3835 (19)	C17—C22	1.3828 (19)
C1—C2	1.387 (2)	C17—C18	1.389 (2)
C2—C3	1.382 (2)	C18—C19	1.3855 (19)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.3987 (19)	C19—C20	1.3939 (19)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.4072 (19)	C20—C21	1.4118 (18)
C5—C6	1.3995 (19)	C21—C22	1.3954 (18)
C5—C10	1.4548 (18)	C21—C26	1.4506 (18)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.5194 (19)	C23—C24	1.5214 (18)
C7—C9	1.5258 (19)	C23—C25	1.5261 (19)
C8—H8A	0.9800	C24—H24A	0.9800
C8—H8B	0.9800	C24—H24B	0.9800
C8—H8C	0.9800	C24—H24C	0.9800
C9—H9A	0.9800	C25—H25A	0.9800
C9—H9B	0.9800	C25—H25B	0.9800
C9—H9C	0.9800	C25—H25C	0.9800
C10—C11	1.4090 (19)	C26—C27	1.4080 (18)
C11—C12	1.4147 (19)	C27—C28	1.4137 (19)
C11—C16	1.4227 (18)	C27—C32	1.4240 (18)
C12—C13	1.370 (2)	C28—C29	1.370 (2)
C12—H12	0.9500	C28—H28	0.9500
C13—C14	1.424 (2)	C29—C30	1.420 (2)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.369 (2)	C30—C31	1.372 (2)
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.4156 (19)	C31—C32	1.4114 (19)
C15—H15	0.9500	C31—H31	0.9500
C4—N1—C7	120.26 (11)	C20—N4—C23	119.47 (11)
C4—N1—H1N	114.6 (11)	C20—N4—H4N	114.1 (11)
C7—N1—H1N	111.3 (11)	C23—N4—H4N	111.7 (11)
C10—N2—N3	115.05 (11)	C26—N5—N6	114.95 (11)
C10—N2—C7	124.91 (11)	C26—N5—C23	124.25 (11)
N3—N2—C7	119.74 (11)	N6—N5—C23	120.24 (10)
N2—N3—C16	103.00 (11)	N5—N6—C32	103.14 (10)
C6—C1—C2	121.31 (13)	C22—C17—C18	121.23 (13)
C6—C1—Cl1	120.29 (11)	C22—C17—Cl2	119.69 (11)
C2—C1—Cl1	118.39 (10)	C18—C17—Cl2	119.08 (11)
C3—C2—C1	119.49 (13)	C19—C18—C17	119.40 (13)
C3—C2—H2	120.3	C19—C18—H18	120.3
C1—C2—H2	120.3	C17—C18—H18	120.3
C2—C3—C4	120.61 (13)	C18—C19—C20	120.59 (13)
C2—C3—H3	119.7	C18—C19—H19	119.7
C4—C3—H3	119.7	C20—C19—H19	119.7
N1—C4—C3	120.82 (12)	N4—C20—C19	121.43 (12)
N1—C4—C5	119.55 (12)	N4—C20—C21	118.93 (12)
C3—C4—C5	119.45 (12)	C19—C20—C21	119.51 (12)
C6—C5—C4	119.58 (12)	C22—C21—C20	119.53 (12)
C6—C5—C10	123.71 (12)	C22—C21—C26	123.40 (12)
C4—C5—C10	116.68 (12)	C20—C21—C26	117.06 (12)
C1—C6—C5	119.54 (13)	C17—C22—C21	119.71 (13)
C1—C6—H6	120.2	C17—C22—H22	120.1
C5—C6—H6	120.2	C21—C22—H22	120.1
N1—C7—N2	105.41 (10)	N4—C23—N5	105.27 (10)
N1—C7—C8	108.36 (11)	N4—C23—C24	108.66 (11)
N2—C7—C8	109.95 (11)	N5—C23—C24	109.72 (11)
N1—C7—C9	112.12 (11)	N4—C23—C25	112.27 (11)
N2—C7—C9	108.61 (11)	N5—C23—C25	108.52 (11)
C8—C7—C9	112.17 (12)	C24—C23—C25	112.16 (12)
C7—C8—H8A	109.5	C23—C24—H24A	109.5
C7—C8—H8B	109.5	C23—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24B	109.5
C7—C8—H8C	109.5	C23—C24—H24C	109.5
H8A—C8—H8C	109.5	H24A—C24—H24C	109.5
H8B—C8—H8C	109.5	H24B—C24—H24C	109.5
C7—C9—H9A	109.5	C23—C25—H25A	109.5
C7—C9—H9B	109.5	C23—C25—H25B	109.5
H9A—C9—H9B	109.5	H25A—C25—H25B	109.5
C7—C9—H9C	109.5	C23—C25—H25C	109.5
H9A—C9—H9C	109.5	H25A—C25—H25C	109.5
H9B—C9—H9C	109.5	H25B—C25—H25C	109.5
N2—C10—C11	105.47 (11)	N5—C26—C27	105.54 (11)
N2—C10—C5	118.79 (12)	N5—C26—C21	118.71 (12)
C11—C10—C5	135.69 (13)	C27—C26—C21	135.74 (12)
C10—C11—C12	135.86 (13)	C26—C27—C28	135.70 (13)
C10—C11—C16	104.30 (12)	C26—C27—C32	104.40 (11)
C12—C11—C16	119.84 (12)	C28—C27—C32	119.90 (12)
C13—C12—C11	118.54 (13)	C29—C28—C27	118.35 (13)
C13—C12—H12	120.7	C29—C28—H28	120.8
C11—C12—H12	120.7	C27—C28—H28	120.8
C12—C13—C14	121.35 (13)	C28—C29—C30	121.35 (13)
C12—C13—H13	119.3	C28—C29—H29	119.3
C14—C13—H13	119.3	C30—C29—H29	119.3
C15—C14—C13	121.50 (13)	C31—C30—C29	121.81 (13)
C15—C14—H14	119.3	C31—C30—H30	119.1
C13—C14—H14	119.3	C29—C30—H30	119.1
C14—C15—C16	117.97 (13)	C30—C31—C32	117.58 (13)
C14—C15—H15	121.0	C30—C31—H31	121.2
C16—C15—H15	121.0	C32—C31—H31	121.2
N3—C16—C15	127.06 (13)	N6—C32—C31	127.08 (12)
N3—C16—C11	112.13 (12)	N6—C32—C27	111.93 (12)
C15—C16—C11	120.80 (13)	C31—C32—C27	120.99 (12)
C10—N2—N3—C16	2.18 (14)	C26—N5—N6—C32	2.02 (14)
C7—N2—N3—C16	176.26 (11)	C23—N5—N6—C32	173.79 (11)
C6—C1—C2—C3	−0.5 (2)	C22—C17—C18—C19	−0.9 (2)
Cl1—C1—C2—C3	178.29 (10)	Cl2—C17—C18—C19	178.41 (10)
C1—C2—C3—C4	1.0 (2)	C17—C18—C19—C20	0.0 (2)
C7—N1—C4—C3	152.54 (13)	C23—N4—C20—C19	150.56 (13)
C7—N1—C4—C5	−32.29 (18)	C23—N4—C20—C21	−33.59 (17)
C2—C3—C4—N1	174.78 (12)	C18—C19—C20—N4	177.17 (12)
C2—C3—C4—C5	−0.4 (2)	C18—C19—C20—C21	1.4 (2)
N1—C4—C5—C6	−175.99 (12)	N4—C20—C21—C22	−177.61 (12)
C3—C4—C5—C6	−0.75 (19)	C19—C20—C21—C22	−1.68 (19)
N1—C4—C5—C10	1.91 (18)	N4—C20—C21—C26	1.62 (18)
C3—C4—C5—C10	177.16 (12)	C19—C20—C21—C26	177.55 (12)
C2—C1—C6—C5	−0.6 (2)	C18—C17—C22—C21	0.6 (2)
Cl1—C1—C6—C5	−179.41 (10)	Cl2—C17—C22—C21	−178.75 (10)
C4—C5—C6—C1	1.3 (2)	C20—C21—C22—C17	0.7 (2)
C10—C5—C6—C1	−176.50 (12)	C26—C21—C22—C17	−178.46 (13)
C4—N1—C7—N2	44.02 (15)	C20—N4—C23—N5	46.66 (15)
C4—N1—C7—C8	161.69 (12)	C20—N4—C23—C24	164.13 (12)
C4—N1—C7—C9	−73.97 (16)	C20—N4—C23—C25	−71.22 (15)
C10—N2—C7—N1	−31.81 (16)	C26—N5—C23—N4	−34.21 (16)
N3—N2—C7—N1	154.73 (11)	N6—N5—C23—N4	154.83 (11)
C10—N2—C7—C8	−148.40 (13)	C26—N5—C23—C24	−150.96 (12)
N3—N2—C7—C8	38.14 (16)	N6—N5—C23—C24	38.07 (16)
C10—N2—C7—C9	88.52 (15)	C26—N5—C23—C25	86.17 (15)
N3—N2—C7—C9	−84.94 (14)	N6—N5—C23—C25	−84.79 (14)
N3—N2—C10—C11	−1.57 (15)	N6—N5—C26—C27	−1.68 (15)
C7—N2—C10—C11	−175.31 (11)	C23—N5—C26—C27	−173.07 (11)
N3—N2—C10—C5	−179.50 (11)	N6—N5—C26—C21	179.01 (11)
C7—N2—C10—C5	6.77 (19)	C23—N5—C26—C21	7.62 (19)
C6—C5—C10—N2	−171.72 (12)	C22—C21—C26—N5	−169.74 (12)
C4—C5—C10—N2	10.47 (18)	C20—C21—C26—N5	11.07 (18)
C6—C5—C10—C11	11.1 (2)	C22—C21—C26—C27	11.2 (2)
C4—C5—C10—C11	−166.67 (14)	C20—C21—C26—C27	−167.98 (14)
N2—C10—C11—C12	−178.65 (15)	N5—C26—C27—C28	−178.92 (15)
C5—C10—C11—C12	−1.3 (3)	C21—C26—C27—C28	0.2 (3)
N2—C10—C11—C16	0.26 (14)	N5—C26—C27—C32	0.58 (14)
C5—C10—C11—C16	177.66 (14)	C21—C26—C27—C32	179.71 (14)
C10—C11—C12—C13	178.45 (15)	C26—C27—C28—C29	−179.44 (14)
C16—C11—C12—C13	−0.33 (19)	C32—C27—C28—C29	1.13 (19)
C11—C12—C13—C14	−0.4 (2)	C27—C28—C29—C30	−1.2 (2)
C12—C13—C14—C15	0.3 (2)	C28—C29—C30—C31	−0.2 (2)
C13—C14—C15—C16	0.5 (2)	C29—C30—C31—C32	1.6 (2)
N2—N3—C16—C15	177.09 (13)	N5—N6—C32—C31	178.35 (13)
N2—N3—C16—C11	−1.92 (14)	N5—N6—C32—C27	−1.56 (14)
C14—C15—C16—N3	179.89 (13)	C30—C31—C32—N6	178.42 (13)
C14—C15—C16—C11	−1.2 (2)	C30—C31—C32—C27	−1.69 (19)
C10—C11—C16—N3	1.08 (15)	C26—C27—C32—N6	0.64 (15)
C12—C11—C16—N3	−179.79 (12)	C28—C27—C32—N6	−179.77 (12)
C10—C11—C16—C15	−178.01 (12)	C26—C27—C32—C31	−179.27 (12)
C12—C11—C16—C15	1.12 (19)	C28—C27—C32—C31	0.32 (19)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N2,N3,C10,C11,C16, N5,N6,C26,C27,C32, C1–C6 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N6	0.896 (18)	2.319 (18)	3.2090 (17)	172.5 (15)
N4—H4n···N3i	0.863 (18)	2.390 (17)	3.2384 (17)	167.5 (15)
C9—H9b···N4ii	0.98	2.58	3.537 (2)	164
C25—H25b···N1	0.98	2.61	3.545 (2)	160
C24—H24c···Cg1i	0.98	2.90	3.8431 (17)	162
C8—H8c···Cg2	0.98	2.97	3.8929 (17)	157
C18—H18···Cg3iii	0.95	2.92	3.6630 (15)	135
C14—H14···Cg4iv	0.95	2.95	3.8062 (16)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N2,N3,C10,C11,C16, N5,N6,C26,C27,C32, C1–C6 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N6	0.90 (2)	2.32 (2)	3.2090 (17)	173 (2)
N4—H4n⋯N3i	0.86 (2)	2.39 (2)	3.2384 (17)	168 (2)
C9—H9b⋯N4ii	0.98	2.58	3.537 (2)	164
C25—H25b⋯N1	0.98	2.61	3.545 (2)	160
C24—H24c⋯Cg1i	0.98	2.90	3.8431 (17)	162
C8—H8c⋯Cg2	0.98	2.97	3.8929 (17)	157
C18—H18⋯Cg3iii	0.95	2.92	3.6630 (15)	135
C14—H14⋯Cg4iv	0.95	2.95	3.8062 (16)	151

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