6-Chloro-3-[5-(3-meth-oxy-8-methyl-4-quinol-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl-quinoline.

In the title compound, C(36)H(29)ClN(4)O, the dihydro-pyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018 Å) are oriented at a dihedral angle of 71.43 (4)°. One of the quinoline rings makes a dihedral angle of 65.40 (7)° with the phenyl substituent. In the crystal, mol-ecules are linked into chains along the b axis by inter-molecular C-H⋯N hydrogen bonds. In addition, C-H⋯π and π-π [centroid-centroid distance = 3.7325 (8) Å] inter-actions are observed.

Related literature

For general background to quinoline and its derivatives, see: Morimoto et al. (1991 ▶); Michael (1997 ▶); Markees et al. (1970 ▶); Campbell et al. (1988 ▶). For applications of quinolines, see: Maguire et al. (1994 ▶); Kalluraya & Sreenivasa (1998 ▶); Roma et al. (2000 ▶); Chen et al. (2001 ▶); Skraup (1880 ▶). For the synthesis of quinoline derivatives, see: Katritzky & Arend (1998 ▶); Jiang & Si (2002 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C36H29ClN4O

M = 569.08

Monoclinic,

a = 14.1209 (3) Å

b = 20.2273 (4) Å

c = 10.1892 (2) Å

β = 95.358 (1)°

V = 2897.6 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.65 × 0.45 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.899, T max = 0.964

57308 measured reflections

10615 independent reflections

8632 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.135

S = 1.08

10615 reflections

495 parameters

All H-atom parameters refined

Δρmax = 0.52 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040252/ci2931sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040252/ci2931Isup2.hkl

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

C36H29ClN4O	F(000) = 1192
Mr = 569.08	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9113 reflections
a = 14.1209 (3) Å	θ = 2.3–32.7°
b = 20.2273 (4) Å	µ = 0.17 mm−1
c = 10.1892 (2) Å	T = 100 K
β = 95.358 (1)°	Block, orange
V = 2897.6 (1) Å3	0.65 × 0.45 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	10615 independent reflections
Radiation source: fine-focus sealed tube	8632 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 32.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→21
Tmin = 0.899, Tmax = 0.964	k = −30→27
57308 measured reflections	l = −15→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0511P)2 + 1.8405P] where P = (Fo2 + 2Fc2)/3
10615 reflections	(Δ/σ)max = 0.001
495 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	1.25829 (2)	0.618905 (17)	0.58916 (3)	0.02412 (8)
O1	0.74552 (8)	0.56821 (5)	−0.26011 (9)	0.0227 (2)
N1	1.06317 (8)	0.82047 (6)	0.24624 (12)	0.0199 (2)
N2	0.79102 (8)	0.76177 (5)	0.05659 (10)	0.0165 (2)
N3	0.72868 (8)	0.74397 (5)	−0.05041 (11)	0.0184 (2)
N4	0.67553 (8)	0.50533 (6)	−0.10704 (11)	0.0192 (2)
C1	1.10707 (9)	0.77113 (6)	0.32078 (14)	0.0194 (2)
C2	1.18398 (11)	0.78906 (8)	0.41257 (17)	0.0300 (3)
C3	1.22949 (11)	0.74267 (8)	0.49378 (17)	0.0293 (3)
C4	1.19938 (9)	0.67648 (7)	0.48422 (13)	0.0201 (2)
C5	1.12617 (9)	0.65686 (6)	0.39571 (13)	0.0178 (2)
C6	1.07802 (9)	0.70427 (6)	0.31049 (12)	0.0164 (2)
C7	0.99820 (9)	0.68861 (6)	0.21888 (12)	0.0158 (2)
C8	0.95183 (9)	0.73961 (6)	0.14831 (12)	0.0151 (2)
C9	0.98850 (9)	0.80588 (6)	0.16423 (12)	0.0163 (2)
C10	0.96496 (10)	0.61872 (6)	0.20841 (13)	0.0204 (3)
C11	1.02484 (14)	0.56977 (8)	0.16651 (16)	0.0306 (3)
C12	0.99534 (18)	0.50358 (8)	0.16652 (19)	0.0442 (5)
C13	0.90824 (17)	0.48653 (9)	0.2083 (2)	0.0462 (5)
C14	0.84867 (14)	0.53492 (8)	0.24773 (19)	0.0397 (5)
C15	0.87629 (11)	0.60117 (7)	0.24724 (15)	0.0256 (3)
C16	0.86764 (9)	0.72709 (6)	0.05412 (12)	0.0155 (2)
C17	0.86503 (10)	0.68158 (7)	−0.06366 (12)	0.0181 (2)
C18	0.75850 (10)	0.68279 (6)	−0.11310 (12)	0.0172 (2)
C19	0.70807 (9)	0.62211 (6)	−0.06680 (12)	0.0172 (2)
C20	0.70797 (9)	0.56215 (6)	−0.14227 (12)	0.0182 (2)
C21	0.63758 (9)	0.50178 (6)	0.01225 (13)	0.0189 (2)
C22	0.60415 (10)	0.43954 (7)	0.05349 (15)	0.0223 (3)
C23	0.56744 (11)	0.43584 (8)	0.17411 (16)	0.0266 (3)
C24	0.56202 (11)	0.49167 (8)	0.25571 (15)	0.0278 (3)
C25	0.59295 (11)	0.55210 (8)	0.21628 (14)	0.0241 (3)
C26	0.63158 (10)	0.55810 (7)	0.09349 (13)	0.0195 (2)
C27	0.66770 (10)	0.61885 (7)	0.04946 (13)	0.0192 (2)
C28	0.63772 (9)	0.77074 (6)	−0.06672 (12)	0.0171 (2)
C29	0.57125 (10)	0.74588 (7)	−0.16539 (14)	0.0222 (3)
C30	0.48047 (11)	0.77291 (8)	−0.18384 (16)	0.0269 (3)
C31	0.45373 (11)	0.82413 (8)	−0.10524 (16)	0.0285 (3)
C32	0.51985 (11)	0.84924 (8)	−0.00833 (14)	0.0265 (3)
C33	0.61164 (10)	0.82371 (7)	0.01109 (13)	0.0207 (2)
C34	0.73866 (13)	0.51077 (8)	−0.34404 (16)	0.0292 (3)
C35	0.60857 (12)	0.38028 (7)	−0.03465 (17)	0.0278 (3)
C36	0.94255 (10)	0.86304 (7)	0.08870 (14)	0.0204 (2)
H2	1.2038 (15)	0.8352 (11)	0.418 (2)	0.039 (6)*
H3	1.2803 (15)	0.7556 (11)	0.559 (2)	0.039 (6)*
H5	1.1052 (13)	0.6108 (9)	0.3924 (18)	0.023 (4)*
H11	1.0823 (13)	0.5813 (9)	0.1388 (17)	0.020 (4)*
H12	1.0391 (18)	0.4749 (13)	0.137 (2)	0.057 (7)*
H13	0.8908 (16)	0.4411 (12)	0.208 (2)	0.046 (6)*
H15	0.8328 (13)	0.6360 (9)	0.2763 (18)	0.025 (5)*
H14	0.7855 (17)	0.5205 (12)	0.275 (2)	0.050 (7)*
H17A	0.9034 (12)	0.7012 (9)	−0.1273 (17)	0.020 (4)*
H17B	0.8907 (12)	0.6379 (9)	−0.0441 (17)	0.017 (4)*
H18	0.7489 (12)	0.6872 (8)	−0.2091 (17)	0.017 (4)*
H22	0.5425 (14)	0.3943 (10)	0.2025 (19)	0.030 (5)*
H24	0.5361 (15)	0.4868 (11)	0.339 (2)	0.041 (6)*
H25	0.5903 (14)	0.5906 (10)	0.271 (2)	0.031 (5)*
H27	0.6655 (13)	0.6569 (9)	0.1041 (18)	0.026 (5)*
H29	0.5881 (13)	0.7098 (10)	−0.2214 (19)	0.028 (5)*
H30	0.4387 (14)	0.7550 (10)	−0.251 (2)	0.030 (5)*
H31	0.3914 (15)	0.8436 (10)	−0.117 (2)	0.037 (5)*
H32	0.5040 (14)	0.8860 (10)	0.0468 (19)	0.029 (5)*
H33	0.6560 (13)	0.8420 (9)	0.0747 (19)	0.027 (5)*
H34A	0.7653 (15)	0.5244 (11)	−0.424 (2)	0.038 (6)*
H34B	0.7735 (15)	0.4747 (11)	−0.298 (2)	0.037 (5)*
H34C	0.6709 (15)	0.4980 (10)	−0.365 (2)	0.033 (5)*
H35A	0.6724 (16)	0.3750 (11)	−0.067 (2)	0.042 (6)*
H35B	0.5669 (16)	0.3864 (11)	−0.115 (2)	0.042 (6)*
H35C	0.5922 (16)	0.3408 (12)	0.011 (2)	0.044 (6)*
H36A	0.9858 (14)	0.8999 (10)	0.0947 (19)	0.027 (5)*
H36B	0.9251 (13)	0.8521 (9)	−0.0029 (19)	0.027 (5)*
H36C	0.8859 (14)	0.8752 (9)	0.127 (2)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02182 (15)	0.02468 (16)	0.02474 (16)	0.00263 (12)	−0.00384 (11)	0.00766 (12)
O1	0.0323 (5)	0.0186 (5)	0.0175 (4)	−0.0014 (4)	0.0039 (4)	−0.0057 (3)
N1	0.0191 (5)	0.0153 (5)	0.0246 (5)	−0.0015 (4)	−0.0016 (4)	0.0040 (4)
N2	0.0211 (5)	0.0145 (5)	0.0131 (4)	0.0007 (4)	−0.0026 (4)	−0.0008 (3)
N3	0.0226 (5)	0.0156 (5)	0.0156 (5)	0.0036 (4)	−0.0048 (4)	−0.0046 (4)
N4	0.0207 (5)	0.0160 (5)	0.0198 (5)	0.0024 (4)	−0.0038 (4)	−0.0019 (4)
C1	0.0174 (5)	0.0162 (6)	0.0237 (6)	−0.0019 (4)	−0.0025 (5)	0.0035 (4)
C2	0.0256 (7)	0.0195 (7)	0.0417 (9)	−0.0067 (5)	−0.0132 (6)	0.0058 (6)
C3	0.0230 (6)	0.0246 (7)	0.0374 (8)	−0.0052 (5)	−0.0128 (6)	0.0063 (6)
C4	0.0182 (5)	0.0206 (6)	0.0208 (6)	0.0015 (5)	−0.0020 (4)	0.0054 (5)
C5	0.0190 (5)	0.0154 (6)	0.0189 (6)	0.0014 (4)	0.0013 (4)	0.0019 (4)
C6	0.0171 (5)	0.0152 (5)	0.0168 (5)	0.0006 (4)	0.0011 (4)	0.0014 (4)
C7	0.0199 (5)	0.0136 (5)	0.0139 (5)	0.0008 (4)	0.0013 (4)	−0.0005 (4)
C8	0.0183 (5)	0.0141 (5)	0.0129 (5)	0.0008 (4)	0.0007 (4)	−0.0008 (4)
C9	0.0178 (5)	0.0146 (5)	0.0168 (5)	0.0004 (4)	0.0022 (4)	0.0021 (4)
C10	0.0307 (7)	0.0128 (5)	0.0160 (5)	0.0004 (5)	−0.0074 (5)	0.0001 (4)
C11	0.0453 (9)	0.0196 (7)	0.0253 (7)	0.0092 (6)	−0.0056 (6)	−0.0045 (5)
C12	0.0746 (14)	0.0187 (7)	0.0349 (9)	0.0165 (8)	−0.0187 (9)	−0.0067 (6)
C13	0.0659 (13)	0.0164 (7)	0.0494 (11)	−0.0091 (8)	−0.0313 (10)	0.0056 (7)
C14	0.0447 (10)	0.0240 (8)	0.0445 (10)	−0.0143 (7)	−0.0266 (8)	0.0164 (7)
C15	0.0305 (7)	0.0187 (6)	0.0247 (7)	−0.0061 (5)	−0.0127 (5)	0.0068 (5)
C16	0.0213 (5)	0.0126 (5)	0.0123 (5)	0.0000 (4)	−0.0001 (4)	−0.0008 (4)
C17	0.0229 (6)	0.0177 (6)	0.0136 (5)	0.0023 (5)	0.0008 (4)	−0.0032 (4)
C18	0.0249 (6)	0.0142 (5)	0.0121 (5)	0.0022 (4)	−0.0012 (4)	−0.0026 (4)
C19	0.0216 (6)	0.0150 (5)	0.0144 (5)	0.0027 (4)	−0.0025 (4)	−0.0019 (4)
C20	0.0202 (6)	0.0173 (6)	0.0161 (5)	0.0028 (4)	−0.0028 (4)	−0.0025 (4)
C21	0.0186 (5)	0.0179 (6)	0.0189 (6)	0.0027 (4)	−0.0052 (4)	0.0015 (4)
C22	0.0199 (6)	0.0182 (6)	0.0272 (7)	0.0015 (5)	−0.0061 (5)	0.0035 (5)
C23	0.0246 (6)	0.0248 (7)	0.0293 (7)	−0.0007 (5)	−0.0041 (5)	0.0087 (5)
C24	0.0286 (7)	0.0325 (8)	0.0217 (7)	0.0011 (6)	−0.0001 (5)	0.0087 (6)
C25	0.0267 (7)	0.0266 (7)	0.0186 (6)	0.0023 (5)	0.0003 (5)	0.0020 (5)
C26	0.0214 (6)	0.0201 (6)	0.0161 (5)	0.0024 (5)	−0.0033 (4)	0.0012 (4)
C27	0.0245 (6)	0.0176 (6)	0.0147 (5)	0.0021 (5)	−0.0020 (4)	−0.0017 (4)
C28	0.0213 (6)	0.0153 (5)	0.0145 (5)	0.0013 (4)	−0.0001 (4)	0.0025 (4)
C29	0.0249 (6)	0.0197 (6)	0.0206 (6)	0.0001 (5)	−0.0042 (5)	0.0003 (5)
C30	0.0233 (6)	0.0290 (7)	0.0270 (7)	−0.0021 (6)	−0.0048 (5)	0.0039 (6)
C31	0.0225 (6)	0.0356 (8)	0.0276 (7)	0.0060 (6)	0.0038 (5)	0.0084 (6)
C32	0.0296 (7)	0.0306 (8)	0.0199 (6)	0.0098 (6)	0.0055 (5)	0.0021 (5)
C33	0.0271 (6)	0.0208 (6)	0.0142 (5)	0.0040 (5)	0.0013 (5)	0.0008 (4)
C34	0.0405 (9)	0.0231 (7)	0.0245 (7)	−0.0018 (6)	0.0062 (6)	−0.0116 (5)
C35	0.0274 (7)	0.0174 (6)	0.0371 (8)	0.0008 (5)	−0.0049 (6)	0.0006 (6)
C36	0.0222 (6)	0.0151 (6)	0.0233 (6)	0.0003 (5)	−0.0005 (5)	0.0043 (5)

Cl1—C4	1.7394 (13)	C17—H17A	0.968 (18)
O1—C20	1.3626 (16)	C17—H17B	0.969 (17)
O1—C34	1.4407 (17)	C18—C19	1.5161 (18)
N1—C9	1.3163 (17)	C18—H18	0.979 (17)
N1—C1	1.3673 (17)	C19—C27	1.3633 (18)
N2—C16	1.2917 (17)	C19—C20	1.4361 (17)
N2—N3	1.3835 (15)	C21—C26	1.4153 (19)
N3—C28	1.3895 (17)	C21—C22	1.4218 (19)
N3—C18	1.4722 (16)	C22—C23	1.380 (2)
N4—C20	1.3001 (17)	C22—C35	1.503 (2)
N4—C21	1.3753 (18)	C23—C24	1.409 (2)
C1—C2	1.413 (2)	C23—H22	0.97 (2)
C1—C6	1.4144 (18)	C24—C25	1.371 (2)
C2—C3	1.371 (2)	C24—H24	0.96 (2)
C2—H2	0.97 (2)	C25—C26	1.4160 (19)
C3—C4	1.405 (2)	C25—H25	0.96 (2)
C3—H3	0.97 (2)	C26—C27	1.4193 (19)
C4—C5	1.3658 (19)	C27—H27	0.952 (19)
C5—C6	1.4232 (18)	C28—C33	1.4023 (18)
C5—H5	0.977 (18)	C28—C29	1.4030 (19)
C6—C7	1.4301 (18)	C29—C30	1.390 (2)
C7—C8	1.3864 (17)	C29—H29	0.969 (19)
C7—C10	1.4904 (18)	C30—C31	1.384 (2)
C8—C9	1.4407 (17)	C30—H30	0.93 (2)
C8—C16	1.4783 (18)	C31—C32	1.390 (2)
C9—C36	1.5022 (18)	C31—H31	0.96 (2)
C10—C15	1.394 (2)	C32—C33	1.392 (2)
C10—C11	1.395 (2)	C32—H32	0.97 (2)
C11—C12	1.402 (3)	C33—H33	0.934 (19)
C11—H11	0.914 (18)	C34—H34A	0.97 (2)
C12—C13	1.382 (4)	C34—H34B	0.97 (2)
C12—H12	0.92 (3)	C34—H34C	1.00 (2)
C13—C14	1.375 (3)	C35—H35A	0.99 (2)
C13—H13	0.95 (2)	C35—H35B	0.97 (2)
C14—C15	1.396 (2)	C35—H35C	0.96 (2)
C14—H14	1.00 (2)	C36—H36A	0.96 (2)
C15—H15	0.998 (19)	C36—H36B	0.97 (2)
C16—C17	1.5101 (17)	C36—H36C	0.96 (2)
C17—C18	1.5413 (19)
C20—O1—C34	116.13 (11)	C19—C18—H18	111.1 (10)
C9—N1—C1	118.93 (11)	C17—C18—H18	111.5 (10)
C16—N2—N3	108.41 (10)	C27—C19—C20	116.41 (12)
N2—N3—C28	120.39 (10)	C27—C19—C18	123.79 (11)
N2—N3—C18	111.96 (10)	C20—C19—C18	119.61 (11)
C28—N3—C18	125.06 (11)	N4—C20—O1	119.93 (11)
C20—N4—C21	117.81 (11)	N4—C20—C19	125.56 (12)
N1—C1—C2	117.45 (12)	O1—C20—C19	114.51 (11)
N1—C1—C6	122.92 (12)	N4—C21—C26	121.64 (12)
C2—C1—C6	119.62 (12)	N4—C21—C22	118.35 (12)
C3—C2—C1	120.80 (14)	C26—C21—C22	120.01 (12)
C3—C2—H2	120.2 (13)	C23—C22—C21	118.29 (13)
C1—C2—H2	119.0 (13)	C23—C22—C35	121.95 (14)
C2—C3—C4	119.24 (13)	C21—C22—C35	119.75 (13)
C2—C3—H3	120.4 (13)	C22—C23—C24	121.87 (14)
C4—C3—H3	120.4 (13)	C22—C23—H22	119.5 (12)
C5—C4—C3	121.87 (12)	C24—C23—H22	118.6 (12)
C5—C4—Cl1	120.03 (11)	C25—C24—C23	120.36 (14)
C3—C4—Cl1	118.10 (10)	C25—C24—H24	120.6 (13)
C4—C5—C6	119.75 (12)	C23—C24—H24	119.0 (13)
C4—C5—H5	120.6 (11)	C24—C25—C26	119.67 (14)
C6—C5—H5	119.7 (11)	C24—C25—H25	121.4 (12)
C1—C6—C5	118.70 (12)	C26—C25—H25	118.9 (12)
C1—C6—C7	117.75 (11)	C21—C26—C25	119.79 (13)
C5—C6—C7	123.47 (12)	C21—C26—C27	117.97 (12)
C8—C7—C6	118.62 (11)	C25—C26—C27	122.21 (13)
C8—C7—C10	122.57 (11)	C19—C27—C26	120.55 (12)
C6—C7—C10	118.72 (11)	C19—C27—H27	120.6 (11)
C7—C8—C9	119.11 (11)	C26—C27—H27	118.8 (11)
C7—C8—C16	121.43 (11)	N3—C28—C33	121.25 (12)
C9—C8—C16	119.43 (11)	N3—C28—C29	119.68 (12)
N1—C9—C8	122.57 (11)	C33—C28—C29	119.05 (12)
N1—C9—C36	115.77 (11)	C30—C29—C28	120.18 (14)
C8—C9—C36	121.66 (11)	C30—C29—H29	119.3 (11)
C15—C10—C11	119.50 (14)	C28—C29—H29	120.5 (11)
C15—C10—C7	120.43 (12)	C31—C30—C29	120.95 (14)
C11—C10—C7	119.97 (14)	C31—C30—H30	121.8 (12)
C10—C11—C12	119.29 (19)	C29—C30—H30	117.3 (12)
C10—C11—H11	119.6 (11)	C30—C31—C32	118.89 (14)
C12—C11—H11	121.1 (11)	C30—C31—H31	122.2 (13)
C13—C12—C11	120.74 (18)	C32—C31—H31	118.9 (13)
C13—C12—H12	126.1 (16)	C31—C32—C33	121.34 (14)
C11—C12—H12	113.2 (16)	C31—C32—H32	121.0 (12)
C14—C13—C12	119.91 (16)	C33—C32—H32	117.6 (12)
C14—C13—H13	121.5 (14)	C32—C33—C28	119.55 (13)
C12—C13—H13	118.5 (14)	C32—C33—H33	120.4 (12)
C13—C14—C15	120.25 (19)	C28—C33—H33	120.0 (12)
C13—C14—H14	117.3 (14)	O1—C34—H34A	105.0 (13)
C15—C14—H14	122.4 (14)	O1—C34—H34B	108.5 (12)
C10—C15—C14	120.28 (17)	H34A—C34—H34B	113.3 (17)
C10—C15—H15	119.9 (11)	O1—C34—H34C	110.3 (12)
C14—C15—H15	119.9 (11)	H34A—C34—H34C	109.5 (17)
N2—C16—C8	121.23 (11)	H34B—C34—H34C	110.0 (17)
N2—C16—C17	112.85 (11)	C22—C35—H35A	111.8 (13)
C8—C16—C17	125.37 (11)	C22—C35—H35B	110.4 (13)
C16—C17—C18	101.58 (10)	H35A—C35—H35B	103.4 (18)
C16—C17—H17A	108.0 (10)	C22—C35—H35C	110.2 (14)
C18—C17—H17A	111.4 (10)	H35A—C35—H35C	109.7 (18)
C16—C17—H17B	114.3 (10)	H35B—C35—H35C	111.2 (18)
C18—C17—H17B	114.6 (10)	C9—C36—H36A	108.8 (12)
H17A—C17—H17B	106.8 (14)	C9—C36—H36B	112.2 (11)
N3—C18—C19	112.57 (11)	H36A—C36—H36B	109.9 (16)
N3—C18—C17	100.46 (10)	C9—C36—H36C	108.9 (12)
C19—C18—C17	110.97 (10)	H36A—C36—H36C	109.1 (16)
N3—C18—H18	109.8 (10)	H36B—C36—H36C	108.0 (16)
C16—N2—N3—C28	175.71 (12)	N2—N3—C18—C19	97.03 (13)
C16—N2—N3—C18	13.06 (14)	C28—N3—C18—C19	−64.65 (16)
C9—N1—C1—C2	−176.86 (14)	N2—N3—C18—C17	−21.06 (13)
C9—N1—C1—C6	2.4 (2)	C28—N3—C18—C17	177.26 (12)
N1—C1—C2—C3	177.85 (16)	C16—C17—C18—N3	19.72 (12)
C6—C1—C2—C3	−1.4 (2)	C16—C17—C18—C19	−99.54 (11)
C1—C2—C3—C4	0.5 (3)	N3—C18—C19—C27	−22.39 (18)
C2—C3—C4—C5	0.3 (2)	C17—C18—C19—C27	89.31 (15)
C2—C3—C4—Cl1	−179.73 (14)	N3—C18—C19—C20	162.75 (11)
C3—C4—C5—C6	−0.3 (2)	C17—C18—C19—C20	−85.55 (14)
Cl1—C4—C5—C6	179.75 (10)	C21—N4—C20—O1	−179.46 (11)
N1—C1—C6—C5	−177.81 (12)	C21—N4—C20—C19	0.3 (2)
C2—C1—C6—C5	1.4 (2)	C34—O1—C20—N4	5.31 (18)
N1—C1—C6—C7	−0.9 (2)	C34—O1—C20—C19	−174.44 (12)
C2—C1—C6—C7	178.31 (13)	C27—C19—C20—N4	−2.2 (2)
C4—C5—C6—C1	−0.57 (19)	C18—C19—C20—N4	172.99 (12)
C4—C5—C6—C7	−177.28 (12)	C27—C19—C20—O1	177.49 (12)
C1—C6—C7—C8	−1.97 (18)	C18—C19—C20—O1	−7.27 (17)
C5—C6—C7—C8	174.77 (12)	C20—N4—C21—C26	1.45 (19)
C1—C6—C7—C10	−178.68 (12)	C20—N4—C21—C22	−178.37 (12)
C5—C6—C7—C10	−1.95 (19)	N4—C21—C22—C23	179.02 (12)
C6—C7—C8—C9	3.31 (17)	C26—C21—C22—C23	−0.81 (19)
C10—C7—C8—C9	179.89 (12)	N4—C21—C22—C35	−1.63 (19)
C6—C7—C8—C16	−178.70 (11)	C26—C21—C22—C35	178.54 (12)
C10—C7—C8—C16	−2.12 (19)	C21—C22—C23—C24	0.3 (2)
C1—N1—C9—C8	−0.94 (19)	C35—C22—C23—C24	−179.01 (14)
C1—N1—C9—C36	178.32 (12)	C22—C23—C24—C25	0.5 (2)
C7—C8—C9—N1	−1.94 (19)	C23—C24—C25—C26	−0.8 (2)
C16—C8—C9—N1	−179.96 (12)	N4—C21—C26—C25	−179.30 (12)
C7—C8—C9—C36	178.85 (12)	C22—C21—C26—C25	0.52 (19)
C16—C8—C9—C36	0.82 (18)	N4—C21—C26—C27	−1.13 (19)
C8—C7—C10—C15	−63.05 (17)	C22—C21—C26—C27	178.69 (12)
C6—C7—C10—C15	113.53 (14)	C24—C25—C26—C21	0.3 (2)
C8—C7—C10—C11	120.55 (15)	C24—C25—C26—C27	−177.82 (14)
C6—C7—C10—C11	−62.87 (17)	C20—C19—C27—C26	2.46 (19)
C15—C10—C11—C12	−1.1 (2)	C18—C19—C27—C26	−172.55 (12)
C7—C10—C11—C12	175.28 (14)	C21—C26—C27—C19	−0.95 (19)
C10—C11—C12—C13	−0.4 (3)	C25—C26—C27—C19	177.18 (13)
C11—C12—C13—C14	1.4 (3)	N2—N3—C28—C33	10.38 (19)
C12—C13—C14—C15	−0.8 (3)	C18—N3—C28—C33	170.62 (12)
C11—C10—C15—C14	1.8 (2)	N2—N3—C28—C29	−171.60 (12)
C7—C10—C15—C14	−174.63 (13)	C18—N3—C28—C29	−11.36 (19)
C13—C14—C15—C10	−0.8 (2)	N3—C28—C29—C30	−179.09 (13)
N3—N2—C16—C8	173.70 (11)	C33—C28—C29—C30	−1.0 (2)
N3—N2—C16—C17	1.81 (15)	C28—C29—C30—C31	−0.5 (2)
C7—C8—C16—N2	131.09 (13)	C29—C30—C31—C32	1.1 (2)
C9—C8—C16—N2	−50.93 (17)	C30—C31—C32—C33	−0.3 (2)
C7—C8—C16—C17	−58.08 (17)	C31—C32—C33—C28	−1.3 (2)
C9—C8—C16—C17	119.90 (14)	N3—C28—C33—C32	179.91 (13)
N2—C16—C17—C18	−14.56 (14)	C29—C28—C33—C32	1.9 (2)
C8—C16—C17—C18	173.95 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N1i	0.95 (2)	2.56 (2)	3.410 (2)	149 (2)
C14—H14···Cg1	1.00 (2)	2.92 (2)	3.685 (2)	134 (2)
C17—H17A···Cg2ii	0.97 (2)	2.55 (2)	3.5018 (14)	169 (1)
C25—H25···Cg3iii	0.96 (2)	2.79 (2)	3.7359 (17)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N1i	0.95 (2)	2.56 (2)	3.410 (2)	149 (2)
C14—H14⋯Cg1	1.00 (2)	2.92 (2)	3.685 (2)	134 (2)
C17—H17A⋯Cg2ii	0.97 (2)	2.55 (2)	3.5018 (14)	169 (1)
C25—H25⋯Cg3iii	0.96 (2)	2.79 (2)	3.7359 (17)	169 (2)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are centroids of the C21–C26, N1/C1/C6–C9 and C28–C33 benzene rings, respectively.