1-[4-(4-Chloro-phen-yl)piperazin-1-yl]-3-(6-oxo-3,4-diphenyl-1,6-dihydro-pyridazin-1-yl)propan-1-one.

In the title compound, C(29)H(27)ClN(4)O(2), the six-membered ring of the pyridazine group is nearly planar [maximum deviation = -0.062 (2) Å] and its mean plane makes dihedral angles of 43.05 (9), 44.71 (10) and 72.57 (9)°, respectively, with the two phenyl and benzene rings. The piperazine ring has a chair conformation and its mean plane is almost perpendicular to the attached benzene ring, with a dihedral angle of 83.20 (16)°. In the crystal, mol-ecules are linked via two pairs of C-H⋯O inter-actions, which result in the formation of chains propagating along [10-1]. Neighbouring chains are linked via C-H⋯π inter-actions.

Related literature

For the synthesis and biological activity of the title compound, see; Doğruer et al. (2007 ▶). For related structures, see: Aydın et al. (2008 ▶); Girisha et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C29H27ClN4O2

M = 499.00

Triclinic,

a = 10.7929 (10) Å

b = 10.8527 (10) Å

c = 12.7815 (13) Å

α = 97.745 (8)°

β = 104.041 (7)°

γ = 115.635 (7)°

V = 1259.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.66 × 0.53 × 0.35 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.784, T max = 0.948

15922 measured reflections

4945 independent reflections

3837 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.05

4945 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203543X/su2489sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203543X/su2489Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203543X/su2489Isup3.cml

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

C29H27ClN4O2	Z = 2
Mr = 499.00	F(000) = 524
Triclinic, P1	Dx = 1.316 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7929 (10) Å	Cell parameters from 24474 reflections
b = 10.8527 (10) Å	θ = 2.2–27.9°
c = 12.7815 (13) Å	µ = 0.19 mm−1
α = 97.745 (8)°	T = 296 K
β = 104.041 (7)°	Prism, colourless
γ = 115.635 (7)°	0.66 × 0.53 × 0.35 mm
V = 1259.3 (2) Å3

Stoe IPDS 2 diffractometer	4945 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3837 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.059
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.784, Tmax = 0.948	l = −15→15
15922 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.165P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4945 reflections	Δρmax = 0.29 e Å−3
326 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	1.08842 (7)	1.37656 (7)	0.23195 (6)	0.0985 (3)
O1	0.77526 (16)	0.94002 (13)	0.89191 (12)	0.0766 (5)
O2	0.37402 (15)	0.69982 (19)	0.55504 (11)	0.0806 (6)
N1	0.63418 (14)	0.70263 (13)	0.85637 (11)	0.0502 (4)
N2	0.61006 (14)	0.57387 (13)	0.87067 (10)	0.0470 (4)
N3	0.52244 (15)	0.69229 (17)	0.46036 (11)	0.0588 (5)
N4	0.68833 (14)	0.88867 (16)	0.35873 (11)	0.0550 (5)
C1	0.75365 (19)	0.83035 (17)	0.91999 (14)	0.0557 (5)
C2	0.84157 (19)	0.82159 (17)	1.01957 (14)	0.0560 (5)
C3	0.81424 (16)	0.69621 (16)	1.04284 (12)	0.0475 (5)
C4	0.69752 (16)	0.56941 (15)	0.95936 (12)	0.0446 (4)
C5	0.66902 (16)	0.42329 (15)	0.96261 (12)	0.0445 (4)
C6	0.7836 (2)	0.39377 (19)	0.99172 (15)	0.0587 (6)
C7	0.7563 (2)	0.2564 (2)	0.98782 (17)	0.0680 (7)
C8	0.6157 (2)	0.1486 (2)	0.95736 (16)	0.0695 (7)
C9	0.5011 (2)	0.17680 (18)	0.93023 (15)	0.0612 (6)
C10	0.52791 (18)	0.31370 (16)	0.93212 (13)	0.0505 (5)
C11	0.89780 (17)	0.69523 (16)	1.15342 (13)	0.0493 (5)
C12	1.04711 (19)	0.78512 (19)	1.20005 (16)	0.0609 (6)
C13	1.1225 (2)	0.7904 (2)	1.30592 (18)	0.0758 (7)
C14	1.0503 (3)	0.7066 (2)	1.36637 (17)	0.0793 (8)
C15	0.9027 (2)	0.6189 (2)	1.32177 (15)	0.0679 (7)
C16	0.8258 (2)	0.61227 (18)	1.21591 (14)	0.0556 (5)
C17	0.53089 (18)	0.69840 (18)	0.75579 (13)	0.0533 (5)
C18	0.58384 (18)	0.69042 (19)	0.65707 (13)	0.0546 (5)
C19	0.48415 (18)	0.69447 (18)	0.55362 (14)	0.0545 (5)
C20	0.45077 (19)	0.7272 (2)	0.36582 (15)	0.0644 (6)
C21	0.54978 (19)	0.8760 (2)	0.36406 (15)	0.0622 (6)
C22	0.76026 (19)	0.8518 (2)	0.45262 (14)	0.0579 (6)
C23	0.66045 (19)	0.7045 (2)	0.45535 (15)	0.0601 (6)
C24	0.78162 (17)	1.00788 (18)	0.33070 (13)	0.0526 (5)
C25	0.7588 (2)	1.1234 (2)	0.32311 (16)	0.0648 (6)
C26	0.8519 (2)	1.2354 (2)	0.29196 (18)	0.0739 (7)
C27	0.9681 (2)	1.2340 (2)	0.26832 (16)	0.0665 (6)
C28	0.9917 (2)	1.1201 (2)	0.27347 (16)	0.0643 (6)
C29	0.89932 (19)	1.00883 (19)	0.30419 (15)	0.0592 (6)
H2	0.92010	0.90490	1.06990	0.0670*
H6	0.87930	0.46690	1.01400	0.0700*
H7	0.83350	0.23700	1.00590	0.0820*
H8	0.59780	0.05620	0.95500	0.0830*
H9	0.40580	0.10380	0.91070	0.0740*
H10	0.45020	0.33220	0.91270	0.0610*
H12	1.09660	0.84210	1.15980	0.0730*
H13	1.22270	0.85080	1.33670	0.0910*
H14	1.10180	0.70970	1.43740	0.0950*
H15	0.85390	0.56340	1.36310	0.0810*
H16	0.72550	0.55220	1.18610	0.0670*
H17A	0.52040	0.78290	0.76920	0.0640*
H17B	0.43600	0.61620	0.73890	0.0640*
H18A	0.68130	0.76950	0.67610	0.0660*
H18B	0.58920	0.60320	0.64150	0.0660*
H20A	0.36040	0.72030	0.37220	0.0770*
H20B	0.42740	0.66010	0.29630	0.0770*
H21A	0.50310	0.89750	0.29950	0.0750*
H21B	0.56740	0.94370	0.43110	0.0750*
H22A	0.78630	0.91950	0.52250	0.0700*
H22B	0.84920	0.85650	0.44460	0.0700*
H23A	0.64250	0.63590	0.38880	0.0720*
H23B	0.70680	0.68350	0.52030	0.0720*
H25	0.68000	1.12540	0.33910	0.0780*
H26	0.83530	1.31200	0.28710	0.0890*
H28	1.06990	1.11840	0.25620	0.0770*
H29	0.91600	0.93200	0.30730	0.0710*

	U11	U22	U33	U12	U13	U23
Cl1	0.0811 (4)	0.0793 (4)	0.1288 (5)	0.0272 (3)	0.0379 (4)	0.0461 (4)
O1	0.0907 (10)	0.0489 (7)	0.0827 (9)	0.0260 (7)	0.0238 (7)	0.0331 (6)
O2	0.0747 (9)	0.1370 (13)	0.0629 (8)	0.0719 (10)	0.0320 (7)	0.0370 (8)
N1	0.0563 (8)	0.0463 (7)	0.0512 (7)	0.0236 (6)	0.0212 (6)	0.0214 (6)
N2	0.0524 (7)	0.0427 (6)	0.0488 (7)	0.0214 (6)	0.0215 (6)	0.0184 (5)
N3	0.0588 (8)	0.0806 (10)	0.0523 (8)	0.0420 (8)	0.0234 (6)	0.0261 (7)
N4	0.0508 (8)	0.0698 (9)	0.0524 (8)	0.0349 (7)	0.0176 (6)	0.0207 (7)
C1	0.0640 (10)	0.0456 (8)	0.0587 (9)	0.0226 (8)	0.0263 (8)	0.0215 (7)
C2	0.0590 (10)	0.0425 (8)	0.0540 (9)	0.0145 (7)	0.0175 (7)	0.0141 (7)
C3	0.0484 (8)	0.0461 (8)	0.0487 (8)	0.0202 (7)	0.0213 (7)	0.0159 (6)
C4	0.0464 (8)	0.0442 (7)	0.0463 (8)	0.0202 (7)	0.0215 (6)	0.0167 (6)
C5	0.0521 (8)	0.0431 (7)	0.0421 (7)	0.0234 (7)	0.0198 (6)	0.0147 (6)
C6	0.0562 (10)	0.0582 (10)	0.0687 (10)	0.0310 (8)	0.0251 (8)	0.0194 (8)
C7	0.0813 (13)	0.0719 (12)	0.0746 (12)	0.0530 (11)	0.0305 (10)	0.0278 (10)
C8	0.1002 (15)	0.0526 (10)	0.0695 (11)	0.0433 (11)	0.0336 (11)	0.0268 (9)
C9	0.0687 (11)	0.0464 (9)	0.0605 (10)	0.0202 (8)	0.0213 (8)	0.0184 (7)
C10	0.0539 (9)	0.0462 (8)	0.0501 (8)	0.0224 (7)	0.0174 (7)	0.0160 (7)
C11	0.0519 (9)	0.0457 (8)	0.0483 (8)	0.0233 (7)	0.0159 (7)	0.0099 (6)
C12	0.0536 (10)	0.0559 (10)	0.0696 (11)	0.0258 (8)	0.0190 (8)	0.0125 (8)
C13	0.0593 (11)	0.0720 (12)	0.0794 (13)	0.0338 (10)	0.0009 (10)	0.0048 (10)
C14	0.0937 (16)	0.0884 (14)	0.0572 (11)	0.0577 (13)	0.0049 (10)	0.0136 (10)
C15	0.0880 (14)	0.0730 (12)	0.0547 (10)	0.0479 (11)	0.0235 (9)	0.0231 (9)
C16	0.0602 (10)	0.0568 (9)	0.0512 (9)	0.0284 (8)	0.0190 (7)	0.0180 (7)
C17	0.0561 (9)	0.0576 (9)	0.0544 (9)	0.0297 (8)	0.0225 (7)	0.0250 (7)
C18	0.0559 (9)	0.0624 (10)	0.0555 (9)	0.0327 (8)	0.0225 (7)	0.0248 (8)
C19	0.0556 (9)	0.0622 (10)	0.0532 (9)	0.0328 (8)	0.0211 (7)	0.0179 (7)
C20	0.0545 (10)	0.0927 (13)	0.0500 (9)	0.0378 (10)	0.0173 (7)	0.0246 (9)
C21	0.0595 (10)	0.0881 (13)	0.0544 (9)	0.0461 (10)	0.0196 (8)	0.0281 (9)
C22	0.0567 (10)	0.0717 (11)	0.0546 (9)	0.0396 (9)	0.0170 (7)	0.0182 (8)
C23	0.0649 (10)	0.0738 (11)	0.0610 (10)	0.0439 (10)	0.0297 (8)	0.0249 (9)
C24	0.0527 (9)	0.0586 (9)	0.0440 (8)	0.0291 (8)	0.0111 (7)	0.0084 (7)
C25	0.0676 (11)	0.0726 (11)	0.0692 (11)	0.0439 (10)	0.0275 (9)	0.0215 (9)
C26	0.0813 (13)	0.0645 (11)	0.0876 (14)	0.0436 (11)	0.0283 (11)	0.0267 (10)
C27	0.0609 (11)	0.0609 (10)	0.0667 (11)	0.0238 (9)	0.0152 (9)	0.0165 (8)
C28	0.0529 (10)	0.0674 (11)	0.0674 (11)	0.0273 (9)	0.0181 (8)	0.0129 (9)
C29	0.0568 (10)	0.0604 (10)	0.0636 (10)	0.0326 (9)	0.0191 (8)	0.0136 (8)

Cl1—C27	1.745 (2)	C24—C25	1.389 (3)
O1—C1	1.231 (2)	C24—C29	1.388 (3)
O2—C19	1.219 (3)	C25—C26	1.383 (3)
N1—N2	1.3532 (19)	C26—C27	1.365 (3)
N1—C1	1.373 (2)	C27—C28	1.372 (3)
N1—C17	1.464 (2)	C28—C29	1.372 (3)
N2—C4	1.309 (2)	C2—H2	0.9300
N3—C19	1.354 (2)	C6—H6	0.9300
N3—C20	1.458 (2)	C7—H7	0.9300
N3—C23	1.455 (3)	C8—H8	0.9300
N4—C21	1.461 (3)	C9—H9	0.9300
N4—C22	1.466 (2)	C10—H10	0.9300
N4—C24	1.410 (2)	C12—H12	0.9300
C1—C2	1.433 (3)	C13—H13	0.9300
C2—C3	1.353 (2)	C14—H14	0.9300
C3—C4	1.439 (2)	C15—H15	0.9300
C3—C11	1.485 (2)	C16—H16	0.9300
C4—C5	1.488 (2)	C17—H17A	0.9700
C5—C6	1.386 (3)	C17—H17B	0.9700
C5—C10	1.381 (3)	C18—H18A	0.9700
C6—C7	1.380 (3)	C18—H18B	0.9700
C7—C8	1.370 (3)	C20—H20A	0.9700
C8—C9	1.375 (3)	C20—H20B	0.9700
C9—C10	1.381 (3)	C21—H21A	0.9700
C11—C12	1.386 (3)	C21—H21B	0.9700
C11—C16	1.394 (3)	C22—H22A	0.9700
C12—C13	1.379 (3)	C22—H22B	0.9700
C13—C14	1.378 (3)	C23—H23A	0.9700
C14—C15	1.367 (4)	C23—H23B	0.9700
C15—C16	1.379 (3)	C25—H25	0.9300
C17—C18	1.513 (3)	C26—H26	0.9300
C18—C19	1.508 (3)	C28—H28	0.9300
C20—C21	1.510 (3)	C29—H29	0.9300
C22—C23	1.504 (3)
Cl1···H7i	3.0900	H6···C11	2.7500
O1···C18	3.252 (2)	H6···H6vii	2.5200
O1···C12ii	3.323 (2)	H7···Cl1xi	3.0900
O2···C25iii	3.289 (3)	H7···H12vii	2.5800
O1···H17A	2.4600	H8···O1xiv	2.9100
O1···H8iv	2.9100	H8···C8viii	3.0000
O1···H2ii	2.8400	H8···C9viii	3.0200
O1···H12ii	2.4400	H8···H8viii	2.5700
O1···H18A	2.7800	H8···H9viii	2.6000
O2···H17B	2.6700	H9···C24v	2.9900
O2···H20A	2.3500	H9···H8viii	2.6000
O2···H17A	2.6100	H10···N2	2.6600
O2···H25iii	2.5300	H10···C3vi	2.9400
N3···N4	2.830 (2)	H10···C4vi	2.9400
N4···N3	2.830 (2)	H12···C2	2.7900
N2···H10	2.6600	H12···H2	2.3800
N2···H20Bv	2.9000	H12···O1ii	2.4400
N3···H18Bv	2.8600	H12···C7vii	3.1000
C5···C16	3.178 (2)	H12···H7vii	2.5800
C6···C11	3.154 (3)	H13···H20Ax	2.4700
C6···C16	3.262 (3)	H14···C25ii	2.9700
C9···C21v	3.595 (3)	H16···C4	2.8800
C9···C24v	3.524 (3)	H16···C5	2.8000
C11···C6	3.154 (3)	H16···H17Bvi	2.4100
C12···O1ii	3.323 (2)	H17A···O1	2.4600
C16···C5	3.178 (2)	H17A···O2	2.6100
C16···C6	3.262 (3)	H17B···O2	2.6700
C18···O1	3.252 (2)	H17B···C16vi	3.1000
C21···C9v	3.595 (3)	H17B···H16vi	2.4100
C24···C9v	3.524 (3)	H18A···O1	2.7800
C25···O2iii	3.289 (3)	H18A···C1	2.9300
C1···H18A	2.9300	H18A···C23	2.7400
C2···H12	2.7900	H18A···H23B	2.2100
C3···H6	2.8700	H18A···C28xiii	3.0600
C3···H10vi	2.9400	H18A···H28xiii	2.2800
C4···H16	2.8800	H18B···C23	2.8800
C4···H10vi	2.9400	H18B···H23B	2.2700
C5···H20Bv	3.0900	H18B···N3v	2.8600
C5···H16	2.8000	H18B···C23v	3.0700
C7···H12vii	3.1000	H20A···O2	2.3500
C8···H8viii	3.0000	H20A···C13xv	2.9500
C9···H21Av	2.9200	H20A···H13xv	2.4700
C9···H8viii	3.0200	H20B···H23A	2.4800
C11···H29ix	2.9200	H20B···N2v	2.9000
C11···H6	2.7500	H20B···C5v	3.0900
C12···H2	2.7100	H21A···C25	2.6900
C12···H29ix	2.9500	H21A···H25	2.2600
C13···H20Ax	2.9500	H21A···C9v	2.9200
C15···H26xi	3.0300	H21B···C25	2.9300
C16···H17Bvi	3.1000	H21B···H22A	2.5100
C18···H23B	2.4500	H21B···H25	2.4500
C21···H25	2.5600	H22A···H21B	2.5100
C22···H29	2.7800	H22B···C29	2.6000
C23···H18B	2.8800	H22B···H29	2.1800
C23···H18Bv	3.0700	H23A···H20B	2.4800
C23···H18A	2.7400	H23B···C18	2.4500
C24···H9v	2.9900	H23B···H18A	2.2100
C25···H21A	2.6900	H23B···H18B	2.2700
C25···H21B	2.9300	H25···C21	2.5600
C25···H14ii	2.9700	H25···H21A	2.2600
C28···H2xii	2.9400	H25···H21B	2.4500
C28···H18Axiii	3.0600	H25···O2iii	2.5300
C29···H22B	2.6000	H26···C15i	3.0300
H2···C12	2.7100	H28···H18Axiii	2.2800
H2···C28ix	2.9400	H29···C11xii	2.9200
H2···H12	2.3800	H29···C12xii	2.9500
H2···O1ii	2.8400	H29···C22	2.7800
H6···C3	2.8700	H29···H22B	2.1800
N2—N1—C1	125.35 (15)	C7—C6—H6	120.00
N2—N1—C17	114.86 (13)	C6—C7—H7	120.00
C1—N1—C17	119.35 (14)	C8—C7—H7	120.00
N1—N2—C4	118.26 (13)	C7—C8—H8	120.00
C19—N3—C20	120.13 (18)	C9—C8—H8	120.00
C19—N3—C23	125.31 (16)	C8—C9—H9	120.00
C20—N3—C23	111.42 (15)	C10—C9—H9	120.00
C21—N4—C22	111.60 (15)	C5—C10—H10	120.00
C21—N4—C24	118.29 (16)	C9—C10—H10	120.00
C22—N4—C24	115.21 (16)	C11—C12—H12	120.00
O1—C1—N1	120.49 (17)	C13—C12—H12	120.00
O1—C1—C2	125.55 (17)	C12—C13—H13	120.00
N1—C1—C2	113.92 (15)	C14—C13—H13	120.00
C1—C2—C3	122.23 (16)	C13—C14—H14	120.00
C2—C3—C4	116.98 (15)	C15—C14—H14	120.00
C2—C3—C11	119.65 (15)	C14—C15—H15	120.00
C4—C3—C11	123.27 (14)	C16—C15—H15	120.00
N2—C4—C3	122.15 (14)	C11—C16—H16	120.00
N2—C4—C5	114.01 (13)	C15—C16—H16	120.00
C3—C4—C5	123.79 (14)	N1—C17—H17A	110.00
C4—C5—C6	120.46 (16)	N1—C17—H17B	110.00
C4—C5—C10	120.58 (17)	C18—C17—H17A	110.00
C6—C5—C10	118.90 (16)	C18—C17—H17B	110.00
C5—C6—C7	120.31 (19)	H17A—C17—H17B	108.00
C6—C7—C8	120.2 (2)	C17—C18—H18A	109.00
C7—C8—C9	120.12 (19)	C17—C18—H18B	109.00
C8—C9—C10	119.85 (19)	C19—C18—H18A	109.00
C5—C10—C9	120.63 (19)	C19—C18—H18B	109.00
C3—C11—C12	120.49 (16)	H18A—C18—H18B	108.00
C3—C11—C16	120.48 (17)	N3—C20—H20A	110.00
C12—C11—C16	118.84 (16)	N3—C20—H20B	110.00
C11—C12—C13	120.20 (18)	C21—C20—H20A	110.00
C12—C13—C14	120.4 (2)	C21—C20—H20B	110.00
C13—C14—C15	119.9 (2)	H20A—C20—H20B	108.00
C14—C15—C16	120.38 (19)	N4—C21—H21A	110.00
C11—C16—C15	120.28 (19)	N4—C21—H21B	110.00
N1—C17—C18	110.42 (17)	C20—C21—H21A	110.00
C17—C18—C19	111.72 (17)	C20—C21—H21B	110.00
O2—C19—N3	121.94 (17)	H21A—C21—H21B	108.00
O2—C19—C18	120.78 (17)	N4—C22—H22A	110.00
N3—C19—C18	117.29 (18)	N4—C22—H22B	110.00
N3—C20—C21	109.95 (16)	C23—C22—H22A	110.00
N4—C21—C20	110.00 (17)	C23—C22—H22B	110.00
N4—C22—C23	110.26 (16)	H22A—C22—H22B	108.00
N3—C23—C22	110.62 (18)	N3—C23—H23A	110.00
N4—C24—C25	123.46 (19)	N3—C23—H23B	110.00
N4—C24—C29	119.06 (17)	C22—C23—H23A	110.00
C25—C24—C29	117.41 (18)	C22—C23—H23B	110.00
C24—C25—C26	120.8 (2)	H23A—C23—H23B	108.00
C25—C26—C27	120.3 (2)	C24—C25—H25	120.00
Cl1—C27—C26	120.62 (17)	C26—C25—H25	120.00
Cl1—C27—C28	119.29 (18)	C25—C26—H26	120.00
C26—C27—C28	120.1 (2)	C27—C26—H26	120.00
C27—C28—C29	119.7 (2)	C27—C28—H28	120.00
C24—C29—C28	121.76 (19)	C29—C28—H28	120.00
C1—C2—H2	119.00	C24—C29—H29	119.00
C3—C2—H2	119.00	C28—C29—H29	119.00
C5—C6—H6	120.00
C1—N1—N2—C4	8.3 (3)	C2—C3—C4—N2	−7.7 (3)
C17—N1—N2—C4	−179.47 (16)	N2—C4—C5—C10	−42.1 (2)
N2—N1—C1—O1	170.70 (18)	C3—C4—C5—C6	−42.2 (2)
C17—N1—C1—O1	−1.2 (3)	C3—C4—C5—C10	140.53 (18)
N2—N1—C1—C2	−11.6 (3)	N2—C4—C5—C6	135.15 (17)
C17—N1—C1—C2	176.54 (17)	C6—C5—C10—C9	−0.2 (2)
N2—N1—C17—C18	−88.78 (18)	C10—C5—C6—C7	1.4 (3)
C1—N1—C17—C18	84.0 (2)	C4—C5—C10—C9	177.05 (15)
N1—N2—C4—C3	2.0 (3)	C4—C5—C6—C7	−175.90 (16)
N1—N2—C4—C5	−175.41 (15)	C5—C6—C7—C8	−1.4 (3)
C20—N3—C19—O2	13.4 (3)	C6—C7—C8—C9	0.2 (3)
C23—N3—C19—O2	171.58 (19)	C7—C8—C9—C10	1.0 (3)
C23—N3—C20—C21	−58.0 (2)	C8—C9—C10—C5	−1.0 (3)
C19—N3—C20—C21	103.0 (2)	C12—C11—C16—C15	−0.7 (3)
C23—N3—C19—C18	−8.3 (3)	C3—C11—C16—C15	−175.65 (18)
C19—N3—C23—C22	−102.3 (2)	C16—C11—C12—C13	0.8 (3)
C20—N3—C19—C18	−166.45 (16)	C3—C11—C12—C13	175.75 (18)
C20—N3—C23—C22	57.50 (19)	C11—C12—C13—C14	0.0 (3)
C24—N4—C21—C20	165.70 (14)	C12—C13—C14—C15	−0.8 (4)
C21—N4—C22—C23	56.4 (2)	C13—C14—C15—C16	0.9 (4)
C22—N4—C21—C20	−57.14 (19)	C14—C15—C16—C11	−0.2 (3)
C24—N4—C22—C23	−165.05 (16)	N1—C17—C18—C19	−176.70 (14)
C22—N4—C24—C25	−126.42 (19)	C17—C18—C19—N3	178.08 (16)
C21—N4—C24—C29	−167.77 (15)	C17—C18—C19—O2	−1.8 (3)
C21—N4—C24—C25	9.3 (2)	N3—C20—C21—N4	57.2 (2)
C22—N4—C24—C29	56.6 (2)	N4—C22—C23—N3	−55.78 (19)
N1—C1—C2—C3	5.0 (3)	N4—C24—C25—C26	−178.06 (17)
O1—C1—C2—C3	−177.4 (2)	C29—C24—C25—C26	−1.0 (3)
C1—C2—C3—C11	−172.67 (19)	N4—C24—C29—C28	178.30 (16)
C1—C2—C3—C4	3.8 (3)	C25—C24—C29—C28	1.1 (3)
C2—C3—C4—C5	169.46 (18)	C24—C25—C26—C27	−0.1 (3)
C11—C3—C4—C5	−14.2 (3)	C25—C26—C27—Cl1	−178.59 (16)
C4—C3—C11—C12	140.70 (19)	C25—C26—C27—C28	1.1 (3)
C4—C3—C11—C16	−44.4 (3)	Cl1—C27—C28—C29	178.70 (15)
C11—C3—C4—N2	168.63 (18)	C26—C27—C28—C29	−1.0 (3)
C2—C3—C11—C12	−43.0 (3)	C27—C28—C29—C24	−0.1 (3)
C2—C3—C11—C16	131.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ii	0.93	2.44	3.323 (2)	158
C25—H25···O2iii	0.93	2.53	3.289 (3)	139
C10—H10···Cg1vi	0.93	2.88	3.431 (2)	119
C29—H29···Cg4xii	0.93	2.86	3.762 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the N1/N2/C1–C4 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.44	3.323 (2)	158
C25—H25⋯O2ii	0.93	2.53	3.289 (3)	139
C10—H10⋯Cg1iii	0.93	2.88	3.431 (2)	119
C29—H29⋯Cg4iv	0.93	2.86	3.762 (2)	165

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