2-Amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile-3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (1/4).

The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.2C(20)H(14)ClN(3)·0.8C(22)H(14)ClN(3), has the atoms of the fused-ring system and those of the amino, cyano and chloro-phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring. There are two independent overlapped mol-ecules in the asymmetric unit. In one independent mol-ecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chloro-phenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second mol-ecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent mol-ecules are linked by N-H⋯N hydrogen bonds into dimers.

Related literature

For similar co-crystals, see: Asiri et al. (2011a ▶,b ▶).

Experimental

Crystal data

0.2C20H14ClN3·0.8C22H14ClN3

M = 351.01

Monoclinic,

a = 19.2576 (7) Å

b = 9.5103 (2) Å

c = 20.2266 (7) Å

β = 114.018 (4)°

V = 3383.7 (2) Å3

Z = 8

Cu Kα radiation

μ = 2.06 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.577, T max = 0.821

12442 measured reflections

6686 independent reflections

6272 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.130

S = 1.05

6686 reflections

471 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040529/zs2147sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040529/zs2147Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040529/zs2147Isup3.cml

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

0.2C20H14ClN3·0.8C22H14ClN3	F(000) = 1452.8
Mr = 351.01	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 9520 reflections
a = 19.2576 (7) Å	θ = 2.5–74.4°
b = 9.5103 (2) Å	µ = 2.06 mm−1
c = 20.2266 (7) Å	T = 100 K
β = 114.018 (4)°	Prism, brown-orange
V = 3383.7 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	6686 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	6272 reflections with I > 2σ(I)
Mirror	Rint = 0.032
Detector resolution: 10.4041 pixels mm-1	θmax = 74.6°, θmin = 2.5°
ω scans	h = −23→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.577, Tmax = 0.821	l = −22→25
12442 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0541P)2 + 4.4722P] where P = (Fo2 + 2Fc2)/3
6686 reflections	(Δ/σ)max = 0.001
471 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.47649 (4)	0.54771 (7)	0.91711 (3)	0.03619 (16)
Cl2	1.19971 (3)	0.62336 (6)	0.76577 (3)	0.02717 (14)
N2	0.41277 (11)	0.3060 (2)	0.46275 (10)	0.0303 (5)
H22	0.3945	0.2761	0.4177	0.036*
H21	0.4590	0.3410	0.4827	0.036*
N3	0.53363 (11)	0.4429 (2)	0.63456 (11)	0.0309 (5)
N5	0.70451 (10)	0.4628 (2)	0.65759 (10)	0.0242 (4)
H52	0.6564	0.4376	0.6390	0.029*
H51	0.7232	0.5107	0.6983	0.029*
N6	0.87451 (11)	0.5819 (2)	0.77852 (10)	0.0249 (4)
C1	0.34901 (12)	0.3426 (2)	0.61038 (11)	0.0185 (4)
C2	0.39635 (11)	0.3465 (2)	0.57321 (11)	0.0188 (4)
C3	0.36991 (12)	0.2981 (2)	0.50123 (11)	0.0213 (4)
C5	0.25137 (11)	0.2336 (2)	0.50655 (11)	0.0173 (4)
C6	0.17630 (11)	0.1630 (2)	0.47299 (11)	0.0175 (4)
C7	0.15869 (12)	0.0681 (2)	0.41558 (11)	0.0219 (4)
H7	0.1960	0.0458	0.3977	0.026*
C8	0.08727 (13)	0.0061 (2)	0.38444 (11)	0.0231 (4)
H8	0.0755	−0.0565	0.3448	0.028*
C9	0.03309 (12)	0.0358 (2)	0.41145 (11)	0.0215 (4)
H9	−0.0160	−0.0057	0.3900	0.026*
C10	0.05081 (12)	0.1262 (2)	0.46977 (11)	0.0200 (4)
H10	0.0139	0.1447	0.4887	0.024*
C11	0.12166 (12)	0.1903 (2)	0.50104 (11)	0.0185 (4)
C12	0.14005 (12)	0.2922 (2)	0.56290 (12)	0.0229 (4)
H12A	0.1067	0.2733	0.5884	0.027*
H12B	0.1302	0.3894	0.5438	0.027*
C13	0.22293 (12)	0.2787 (2)	0.61594 (11)	0.0225 (4)
H13A	0.2355	0.3544	0.6526	0.027*
H13B	0.2307	0.1873	0.6414	0.027*
C14	0.27531 (12)	0.2883 (2)	0.57713 (11)	0.0192 (4)
C15	0.38013 (12)	0.3938 (2)	0.68678 (11)	0.0199 (4)
C16	0.36942 (14)	0.5320 (3)	0.70204 (12)	0.0281 (5)
H16	0.3417	0.5943	0.6636	0.034*
C17	0.39890 (14)	0.5809 (3)	0.77331 (13)	0.0290 (5)
H17	0.3911	0.6754	0.7839	0.035*
C18	0.43959 (13)	0.4887 (3)	0.82785 (11)	0.0247 (5)
C19	0.45232 (13)	0.3507 (3)	0.81436 (12)	0.0260 (5)
H19	0.4810	0.2894	0.8529	0.031*
C20	0.42214 (13)	0.3036 (2)	0.74306 (12)	0.0236 (4)
H20	0.4303	0.2091	0.7327	0.028*
C22	0.47249 (12)	0.4012 (2)	0.60785 (11)	0.0229 (4)
C23	0.87585 (11)	0.4285 (2)	0.61845 (11)	0.0175 (4)
C24	0.82793 (12)	0.4631 (2)	0.65336 (11)	0.0183 (4)
C25	0.75014 (12)	0.4275 (2)	0.62329 (11)	0.0190 (4)
C27	0.77056 (12)	0.3061 (2)	0.52568 (11)	0.0184 (4)
C28	0.74168 (11)	0.2139 (2)	0.46097 (11)	0.0185 (4)
C29	0.68059 (13)	0.1213 (2)	0.44618 (12)	0.0233 (4)
H29	0.6585	0.1112	0.4802	0.028*
C30	0.65195 (13)	0.0441 (2)	0.38272 (13)	0.0264 (5)
H30	0.6097	−0.0166	0.3729	0.032*
C31	0.68490 (14)	0.0557 (3)	0.33362 (13)	0.0276 (5)
H31	0.6638	0.0062	0.2890	0.033*
C32	0.74870 (13)	0.1394 (2)	0.34957 (12)	0.0244 (5)
H32	0.7727	0.1431	0.3168	0.029*
C33	0.77796 (12)	0.2181 (2)	0.41305 (11)	0.0197 (4)
C34	0.84650 (12)	0.3108 (2)	0.43101 (11)	0.0217 (4)
H34A	0.8298	0.4075	0.4137	0.026*
H34B	0.8776	0.2755	0.4058	0.026*
C35	0.89469 (12)	0.3136 (2)	0.51267 (11)	0.0202 (4)
H35A	0.9183	0.2203	0.5286	0.024*
H35B	0.9360	0.3836	0.5236	0.024*
C36	0.84698 (12)	0.3508 (2)	0.55402 (11)	0.0178 (4)
C37	0.95655 (11)	0.4762 (2)	0.65269 (10)	0.0171 (4)
C38	1.01649 (12)	0.3796 (2)	0.67461 (11)	0.0190 (4)
H38	1.0058	0.2822	0.6658	0.023*
C39	1.09139 (12)	0.4242 (2)	0.70914 (11)	0.0194 (4)
H39	1.1319	0.3582	0.7243	0.023*
C40	1.10595 (12)	0.5666 (2)	0.72103 (11)	0.0197 (4)
C41	1.04796 (12)	0.6654 (2)	0.69953 (11)	0.0206 (4)
H41	1.0592	0.7627	0.7078	0.025*
C42	0.97326 (12)	0.6197 (2)	0.66573 (11)	0.0201 (4)
H42	0.9330	0.6863	0.6513	0.024*
C44	0.85661 (11)	0.5307 (2)	0.72266 (11)	0.0196 (4)
N1	0.26563 (17)	0.2046 (3)	0.32991 (15)	0.0287 (6)	0.67
N4	0.57603 (11)	0.3302 (2)	0.49932 (11)	0.0265 (4)	0.93
C4	0.29686 (11)	0.2425 (2)	0.46910 (10)	0.0181 (4)	0.67
C21	0.2743 (2)	0.2161 (4)	0.3913 (2)	0.0298 (8)	0.67
C26	0.72231 (11)	0.3513 (2)	0.55831 (11)	0.0186 (4)	0.93
C43	0.64133 (13)	0.3348 (2)	0.52387 (12)	0.0205 (5)	0.93
N4'	0.29686 (11)	0.2425 (2)	0.46910 (10)	0.0181 (4)	0.33
N26'	0.72231 (11)	0.3513 (2)	0.55831 (11)	0.0186 (4)	0.07

	U11	U22	U33	U12	U13	U23
Cl1	0.0500 (4)	0.0405 (3)	0.0163 (3)	−0.0087 (3)	0.0117 (2)	−0.0076 (2)
Cl2	0.0201 (2)	0.0315 (3)	0.0268 (3)	−0.0075 (2)	0.0064 (2)	0.0028 (2)
N2	0.0256 (10)	0.0490 (13)	0.0178 (9)	0.0029 (9)	0.0103 (8)	−0.0021 (9)
N3	0.0229 (10)	0.0450 (13)	0.0250 (10)	−0.0089 (9)	0.0099 (8)	−0.0051 (9)
N5	0.0183 (9)	0.0361 (11)	0.0202 (9)	−0.0021 (8)	0.0097 (7)	−0.0072 (8)
N6	0.0239 (9)	0.0276 (10)	0.0226 (10)	−0.0002 (8)	0.0088 (8)	−0.0034 (8)
C1	0.0183 (10)	0.0193 (10)	0.0160 (9)	0.0014 (8)	0.0050 (8)	0.0006 (8)
C2	0.0164 (9)	0.0202 (10)	0.0170 (10)	−0.0019 (8)	0.0038 (8)	−0.0013 (8)
C3	0.0209 (10)	0.0239 (11)	0.0172 (10)	0.0028 (8)	0.0058 (8)	−0.0002 (8)
C5	0.0179 (9)	0.0168 (10)	0.0169 (9)	0.0022 (7)	0.0068 (8)	0.0019 (7)
C6	0.0176 (9)	0.0185 (10)	0.0156 (9)	0.0004 (8)	0.0059 (8)	0.0029 (8)
C7	0.0244 (10)	0.0267 (11)	0.0158 (9)	0.0011 (9)	0.0093 (8)	−0.0003 (8)
C8	0.0278 (11)	0.0230 (11)	0.0162 (10)	−0.0042 (9)	0.0067 (8)	−0.0023 (8)
C9	0.0213 (10)	0.0220 (10)	0.0184 (10)	−0.0041 (8)	0.0051 (8)	0.0019 (8)
C10	0.0189 (10)	0.0220 (10)	0.0202 (10)	−0.0015 (8)	0.0090 (8)	0.0023 (8)
C11	0.0195 (10)	0.0182 (10)	0.0181 (10)	0.0000 (8)	0.0077 (8)	0.0001 (8)
C12	0.0191 (10)	0.0258 (11)	0.0254 (11)	−0.0016 (8)	0.0107 (9)	−0.0085 (9)
C13	0.0219 (10)	0.0282 (11)	0.0189 (10)	−0.0028 (9)	0.0098 (8)	−0.0043 (8)
C14	0.0189 (10)	0.0219 (10)	0.0169 (9)	0.0005 (8)	0.0073 (8)	0.0013 (8)
C15	0.0165 (9)	0.0267 (11)	0.0164 (9)	−0.0033 (8)	0.0067 (8)	−0.0026 (8)
C16	0.0311 (12)	0.0282 (12)	0.0201 (11)	0.0059 (9)	0.0054 (9)	0.0002 (9)
C17	0.0344 (12)	0.0249 (12)	0.0253 (11)	0.0020 (10)	0.0097 (10)	−0.0068 (9)
C18	0.0272 (11)	0.0333 (12)	0.0145 (10)	−0.0063 (9)	0.0094 (8)	−0.0056 (9)
C19	0.0300 (12)	0.0289 (12)	0.0174 (10)	−0.0014 (9)	0.0080 (9)	0.0028 (9)
C20	0.0264 (11)	0.0236 (11)	0.0201 (10)	−0.0005 (9)	0.0089 (9)	−0.0009 (8)
C22	0.0223 (11)	0.0287 (11)	0.0190 (10)	−0.0021 (9)	0.0096 (9)	−0.0024 (8)
C23	0.0178 (10)	0.0164 (10)	0.0174 (9)	0.0020 (7)	0.0063 (8)	0.0031 (8)
C24	0.0193 (10)	0.0193 (10)	0.0156 (9)	0.0009 (8)	0.0065 (8)	0.0008 (8)
C25	0.0190 (10)	0.0210 (10)	0.0178 (9)	0.0027 (8)	0.0083 (8)	0.0028 (8)
C27	0.0205 (10)	0.0174 (10)	0.0176 (9)	0.0017 (8)	0.0079 (8)	0.0039 (8)
C28	0.0181 (9)	0.0181 (10)	0.0179 (9)	0.0024 (8)	0.0058 (8)	0.0034 (8)
C29	0.0233 (10)	0.0235 (11)	0.0237 (11)	−0.0017 (8)	0.0100 (9)	0.0009 (9)
C30	0.0261 (11)	0.0223 (11)	0.0285 (11)	−0.0052 (9)	0.0087 (9)	−0.0027 (9)
C31	0.0334 (12)	0.0235 (11)	0.0230 (11)	−0.0029 (9)	0.0086 (9)	−0.0050 (9)
C32	0.0306 (11)	0.0226 (11)	0.0218 (10)	−0.0021 (9)	0.0125 (9)	−0.0024 (8)
C33	0.0223 (10)	0.0164 (10)	0.0198 (10)	0.0007 (8)	0.0081 (8)	0.0025 (8)
C34	0.0256 (11)	0.0225 (11)	0.0193 (10)	−0.0043 (8)	0.0114 (9)	0.0002 (8)
C35	0.0205 (10)	0.0222 (10)	0.0199 (10)	−0.0001 (8)	0.0103 (8)	0.0009 (8)
C36	0.0188 (10)	0.0184 (10)	0.0168 (9)	0.0016 (8)	0.0080 (8)	0.0028 (8)
C37	0.0178 (10)	0.0203 (10)	0.0140 (9)	−0.0010 (8)	0.0074 (8)	0.0002 (7)
C38	0.0210 (10)	0.0186 (10)	0.0187 (10)	−0.0004 (8)	0.0093 (8)	0.0006 (8)
C39	0.0176 (9)	0.0241 (11)	0.0175 (9)	0.0023 (8)	0.0082 (8)	0.0007 (8)
C40	0.0174 (9)	0.0268 (11)	0.0151 (9)	−0.0059 (8)	0.0066 (8)	0.0011 (8)
C41	0.0249 (10)	0.0187 (10)	0.0185 (10)	−0.0035 (8)	0.0092 (8)	0.0016 (8)
C42	0.0222 (10)	0.0204 (10)	0.0186 (10)	0.0017 (8)	0.0092 (8)	0.0031 (8)
C44	0.0163 (9)	0.0205 (10)	0.0220 (10)	0.0015 (8)	0.0077 (8)	0.0013 (8)
N1	0.0317 (15)	0.0271 (15)	0.0198 (14)	−0.0052 (12)	0.0027 (12)	−0.0082 (11)
N4	0.0202 (10)	0.0335 (12)	0.0266 (10)	−0.0015 (8)	0.0102 (8)	−0.0057 (9)
C4	0.0170 (9)	0.0197 (9)	0.0160 (9)	0.0020 (7)	0.0052 (7)	−0.0002 (7)
C21	0.0244 (17)	0.0307 (19)	0.034 (2)	−0.0111 (14)	0.0118 (15)	−0.0104 (15)
C26	0.0175 (9)	0.0204 (10)	0.0183 (9)	0.0001 (8)	0.0076 (8)	0.0008 (8)
C43	0.0246 (12)	0.0213 (11)	0.0175 (10)	0.0004 (9)	0.0105 (9)	−0.0031 (8)
N4'	0.0170 (9)	0.0197 (9)	0.0160 (9)	0.0020 (7)	0.0052 (7)	−0.0002 (7)
N26'	0.0175 (9)	0.0204 (10)	0.0183 (9)	0.0001 (8)	0.0076 (8)	0.0008 (8)

Cl1—C18	1.742 (2)	C19—C20	1.392 (3)
Cl2—C40	1.744 (2)	C19—H19	0.9500
N2—C3	1.348 (3)	C20—H20	0.9500
N2—H22	0.8800	C23—C36	1.401 (3)
N2—H21	0.8800	C23—C24	1.410 (3)
N3—C22	1.148 (3)	C23—C37	1.491 (3)
N5—C25	1.364 (3)	C24—C25	1.410 (3)
N5—H52	0.8800	C24—C44	1.433 (3)
N5—H51	0.8800	C25—C26	1.403 (3)
N6—C44	1.147 (3)	C27—C26	1.408 (3)
C1—C14	1.399 (3)	C27—C36	1.410 (3)
C1—C2	1.399 (3)	C27—C28	1.483 (3)
C1—C15	1.493 (3)	C28—C29	1.402 (3)
C2—C3	1.410 (3)	C28—C33	1.407 (3)
C2—C22	1.441 (3)	C29—C30	1.383 (3)
C3—C4	1.392 (3)	C29—H29	0.9500
C5—C4	1.374 (3)	C30—C31	1.383 (3)
C5—C14	1.409 (3)	C30—H30	0.9500
C5—C6	1.484 (3)	C31—C32	1.388 (3)
C6—C7	1.399 (3)	C31—H31	0.9500
C6—C11	1.408 (3)	C32—C33	1.392 (3)
C7—C8	1.390 (3)	C32—H32	0.9500
C7—H7	0.9500	C33—C34	1.504 (3)
C8—C9	1.390 (3)	C34—C35	1.530 (3)
C8—H8	0.9500	C34—H34A	0.9900
C9—C10	1.385 (3)	C34—H34B	0.9900
C9—H9	0.9500	C35—C36	1.515 (3)
C10—C11	1.390 (3)	C35—H35A	0.9900
C10—H10	0.9500	C35—H35B	0.9900
C11—C12	1.506 (3)	C37—C38	1.399 (3)
C12—C13	1.524 (3)	C37—C42	1.402 (3)
C12—H12A	0.9900	C38—C39	1.389 (3)
C12—H12B	0.9900	C38—H38	0.9500
C13—C14	1.512 (3)	C39—C40	1.384 (3)
C13—H13A	0.9900	C39—H39	0.9500
C13—H13B	0.9900	C40—C41	1.387 (3)
C15—C16	1.385 (3)	C41—C42	1.388 (3)
C15—C20	1.392 (3)	C41—H41	0.9500
C16—C17	1.396 (3)	C42—H42	0.9500
C16—H16	0.9500	N1—C21	1.188 (5)
C17—C18	1.377 (3)	N4—C43	1.150 (3)
C17—H17	0.9500	C4—C21	1.474 (4)
C18—C19	1.383 (3)	C26—C43	1.434 (3)
C3—N2—H22	120.0	C36—C23—C37	122.42 (18)
C3—N2—H21	120.0	C24—C23—C37	117.86 (18)
H22—N2—H21	120.0	C23—C24—C25	121.68 (19)
C25—N5—H52	120.0	C23—C24—C44	121.61 (19)
C25—N5—H51	120.0	C25—C24—C44	116.65 (18)
H52—N5—H51	120.0	N5—C25—C26	121.59 (19)
C14—C1—C2	120.48 (19)	N5—C25—C24	120.86 (19)
C14—C1—C15	121.29 (18)	C26—C25—C24	117.52 (18)
C2—C1—C15	118.21 (18)	C26—C27—C36	119.75 (19)
C1—C2—C3	120.40 (19)	C26—C27—C28	120.81 (19)
C1—C2—C22	120.36 (19)	C36—C27—C28	119.44 (18)
C3—C2—C22	119.24 (19)	C29—C28—C33	118.7 (2)
N2—C3—C4	119.46 (19)	C29—C28—C27	122.74 (19)
N2—C3—C2	122.0 (2)	C33—C28—C27	118.57 (19)
C4—C3—C2	118.55 (19)	C30—C29—C28	121.0 (2)
C4—C5—C14	121.11 (19)	C30—C29—H29	119.5
C4—C5—C6	119.78 (18)	C28—C29—H29	119.5
C14—C5—C6	119.11 (18)	C31—C30—C29	119.9 (2)
C7—C6—C11	119.01 (19)	C31—C30—H30	120.1
C7—C6—C5	122.22 (19)	C29—C30—H30	120.1
C11—C6—C5	118.75 (18)	C30—C31—C32	120.0 (2)
C8—C7—C6	120.7 (2)	C30—C31—H31	120.0
C8—C7—H7	119.6	C32—C31—H31	120.0
C6—C7—H7	119.6	C31—C32—C33	120.7 (2)
C7—C8—C9	119.9 (2)	C31—C32—H32	119.6
C7—C8—H8	120.0	C33—C32—H32	119.6
C9—C8—H8	120.0	C32—C33—C28	119.5 (2)
C10—C9—C8	119.8 (2)	C32—C33—C34	121.61 (19)
C10—C9—H9	120.1	C28—C33—C34	118.90 (19)
C8—C9—H9	120.1	C33—C34—C35	110.99 (17)
C9—C10—C11	121.05 (19)	C33—C34—H34A	109.4
C9—C10—H10	119.5	C35—C34—H34A	109.4
C11—C10—H10	119.5	C33—C34—H34B	109.4
C10—C11—C6	119.47 (19)	C35—C34—H34B	109.4
C10—C11—C12	121.04 (18)	H34A—C34—H34B	108.0
C6—C11—C12	119.46 (18)	C36—C35—C34	111.25 (17)
C11—C12—C13	110.83 (18)	C36—C35—H35A	109.4
C11—C12—H12A	109.5	C34—C35—H35A	109.4
C13—C12—H12A	109.5	C36—C35—H35B	109.4
C11—C12—H12B	109.5	C34—C35—H35B	109.4
C13—C12—H12B	109.5	H35A—C35—H35B	108.0
H12A—C12—H12B	108.1	C23—C36—C27	119.37 (18)
C14—C13—C12	111.00 (17)	C23—C36—C35	122.44 (18)
C14—C13—H13A	109.4	C27—C36—C35	118.19 (18)
C12—C13—H13A	109.4	C38—C37—C42	118.88 (19)
C14—C13—H13B	109.4	C38—C37—C23	121.14 (19)
C12—C13—H13B	109.4	C42—C37—C23	119.94 (19)
H13A—C13—H13B	108.0	C39—C38—C37	120.9 (2)
C1—C14—C5	118.23 (18)	C39—C38—H38	119.6
C1—C14—C13	122.24 (18)	C37—C38—H38	119.6
C5—C14—C13	119.42 (18)	C40—C39—C38	118.8 (2)
C16—C15—C20	119.5 (2)	C40—C39—H39	120.6
C16—C15—C1	120.5 (2)	C38—C39—H39	120.6
C20—C15—C1	120.0 (2)	C39—C40—C41	121.9 (2)
C15—C16—C17	120.7 (2)	C39—C40—Cl2	119.12 (17)
C15—C16—H16	119.6	C41—C40—Cl2	119.01 (17)
C17—C16—H16	119.6	C40—C41—C42	118.9 (2)
C18—C17—C16	118.4 (2)	C40—C41—H41	120.5
C18—C17—H17	120.8	C42—C41—H41	120.5
C16—C17—H17	120.8	C41—C42—C37	120.7 (2)
C17—C18—C19	122.3 (2)	C41—C42—H42	119.7
C17—C18—Cl1	118.97 (19)	C37—C42—H42	119.7
C19—C18—Cl1	118.69 (18)	N6—C44—C24	174.8 (2)
C18—C19—C20	118.5 (2)	C5—C4—C3	121.06 (18)
C18—C19—H19	120.7	C5—C4—C21	127.0 (2)
C20—C19—H19	120.7	C3—C4—C21	111.5 (2)
C15—C20—C19	120.5 (2)	N1—C21—C4	170.5 (3)
C15—C20—H20	119.8	C25—C26—C27	121.57 (19)
C19—C20—H20	119.8	C25—C26—C43	115.91 (18)
N3—C22—C2	178.6 (2)	C27—C26—C43	122.23 (19)
C36—C23—C24	119.72 (19)	N4—C43—C26	174.8 (2)
C14—C1—C2—C3	1.1 (3)	C26—C27—C28—C29	−27.3 (3)
C15—C1—C2—C3	179.4 (2)	C36—C27—C28—C29	153.8 (2)
C14—C1—C2—C22	−179.4 (2)	C26—C27—C28—C33	153.8 (2)
C15—C1—C2—C22	−1.2 (3)	C36—C27—C28—C33	−25.2 (3)
C1—C2—C3—N2	177.0 (2)	C33—C28—C29—C30	−5.6 (3)
C22—C2—C3—N2	−2.4 (3)	C27—C28—C29—C30	175.5 (2)
C1—C2—C3—C4	−2.0 (3)	C28—C29—C30—C31	1.5 (4)
C22—C2—C3—C4	178.5 (2)	C29—C30—C31—C32	3.0 (4)
C4—C5—C6—C7	20.2 (3)	C30—C31—C32—C33	−3.3 (4)
C14—C5—C6—C7	−158.7 (2)	C31—C32—C33—C28	−0.9 (3)
C4—C5—C6—C11	−161.23 (19)	C31—C32—C33—C34	−179.3 (2)
C14—C5—C6—C11	19.9 (3)	C29—C28—C33—C32	5.2 (3)
C11—C6—C7—C8	2.8 (3)	C27—C28—C33—C32	−175.78 (19)
C5—C6—C7—C8	−178.7 (2)	C29—C28—C33—C34	−176.3 (2)
C6—C7—C8—C9	−1.5 (3)	C27—C28—C33—C34	2.7 (3)
C7—C8—C9—C10	−0.6 (3)	C32—C33—C34—C35	−145.8 (2)
C8—C9—C10—C11	1.3 (3)	C28—C33—C34—C35	35.8 (3)
C9—C10—C11—C6	0.0 (3)	C33—C34—C35—C36	−52.5 (2)
C9—C10—C11—C12	178.0 (2)	C24—C23—C36—C27	−1.1 (3)
C7—C6—C11—C10	−2.1 (3)	C37—C23—C36—C27	178.39 (19)
C5—C6—C11—C10	179.36 (19)	C24—C23—C36—C35	178.23 (19)
C7—C6—C11—C12	179.9 (2)	C37—C23—C36—C35	−2.2 (3)
C5—C6—C11—C12	1.3 (3)	C26—C27—C36—C23	6.1 (3)
C10—C11—C12—C13	144.7 (2)	C28—C27—C36—C23	−174.91 (18)
C6—C11—C12—C13	−37.3 (3)	C26—C27—C36—C35	−173.26 (19)
C11—C12—C13—C14	51.9 (3)	C28—C27—C36—C35	5.7 (3)
C2—C1—C14—C5	2.2 (3)	C34—C35—C36—C23	−146.4 (2)
C15—C1—C14—C5	−175.98 (19)	C34—C35—C36—C27	33.0 (3)
C2—C1—C14—C13	178.4 (2)	C36—C23—C37—C38	−59.7 (3)
C15—C1—C14—C13	0.2 (3)	C24—C23—C37—C38	119.9 (2)
C4—C5—C14—C1	−4.8 (3)	C36—C23—C37—C42	122.6 (2)
C6—C5—C14—C1	174.13 (19)	C24—C23—C37—C42	−57.8 (3)
C4—C5—C14—C13	178.92 (19)	C42—C37—C38—C39	0.4 (3)
C6—C5—C14—C13	−2.2 (3)	C23—C37—C38—C39	−177.34 (18)
C12—C13—C14—C1	150.0 (2)	C37—C38—C39—C40	−0.5 (3)
C12—C13—C14—C5	−33.9 (3)	C38—C39—C40—C41	0.1 (3)
C14—C1—C15—C16	−88.5 (3)	C38—C39—C40—Cl2	178.87 (15)
C2—C1—C15—C16	93.3 (3)	C39—C40—C41—C42	0.6 (3)
C14—C1—C15—C20	93.4 (3)	Cl2—C40—C41—C42	−178.23 (15)
C2—C1—C15—C20	−84.8 (3)	C40—C41—C42—C37	−0.8 (3)
C20—C15—C16—C17	−1.4 (4)	C38—C37—C42—C41	0.3 (3)
C1—C15—C16—C17	−179.5 (2)	C23—C37—C42—C41	178.03 (18)
C15—C16—C17—C18	0.8 (4)	C14—C5—C4—C3	4.0 (3)
C16—C17—C18—C19	0.3 (4)	C6—C5—C4—C3	−174.93 (19)
C16—C17—C18—Cl1	−179.78 (19)	C14—C5—C4—C21	−167.1 (3)
C17—C18—C19—C20	−0.7 (4)	C6—C5—C4—C21	14.1 (4)
Cl1—C18—C19—C20	179.38 (17)	N2—C3—C4—C5	−179.6 (2)
C16—C15—C20—C19	1.0 (3)	C2—C3—C4—C5	−0.5 (3)
C1—C15—C20—C19	179.1 (2)	N2—C3—C4—C21	−7.3 (3)
C18—C19—C20—C15	0.0 (3)	C2—C3—C4—C21	171.8 (2)
C36—C23—C24—C25	−3.2 (3)	N5—C25—C26—C27	−175.3 (2)
C37—C23—C24—C25	177.26 (19)	C24—C25—C26—C27	2.8 (3)
C36—C23—C24—C44	174.06 (19)	N5—C25—C26—C43	10.7 (3)
C37—C23—C24—C44	−5.5 (3)	C24—C25—C26—C43	−171.22 (19)
C23—C24—C25—N5	−179.5 (2)	C36—C27—C26—C25	−7.1 (3)
C44—C24—C25—N5	3.1 (3)	C28—C27—C26—C25	174.00 (19)
C23—C24—C25—C26	2.4 (3)	C36—C27—C26—C43	166.5 (2)
C44—C24—C25—C26	−175.01 (19)	C28—C27—C26—C43	−12.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N4	0.88	2.14	2.931 (3)	149
N5—H52···N3	0.88	2.33	3.136 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N4	0.88	2.14	2.931 (3)	149
N5—H52⋯N3	0.88	2.33	3.136 (3)	152