3,5-Bis[1-acetyl-5-(4-chloro-phen-yl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethyl-pyridine.

The title compound, C(29)H(27)Cl(2)N(5)O(2), contains a central pyridine ring and two functionalized pyrazoline rings. The pyridine ring and the two attached pyrazoline rings are nearly coplanar, whereas the terminal chloro-phenyl rings are nearly perpendicular to the attached pyrazoline rings [dihedral angles = 86.78 (1) and 77.70 (1)°]. Mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonding.

Related literature

For general background, see: Ahn et al. (2004 ▶); Palaska et al. (1996 ▶); Yar et al. (2006 ▶)

Experimental

Crystal data

C29H27Cl2N5O2

M = 548.46

Monoclinic,

a = 12.345 (3) Å

b = 9.6763 (19) Å

c = 13.268 (3) Å

β = 115.00 (3)°

V = 1436.4 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.950

7509 measured reflections

3736 independent reflections

2520 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.077

S = 0.91

3736 reflections

344 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1031 Friedel pairs

Flack parameter: 0.06 (6)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023921/xu2444sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023921/xu2444Isup2.hkl

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

C29H27Cl2N5O2	F000 = 572
Mr = 548.46	Dx = 1.268 Mg m−3
Monoclinic, P21	Melting point = 547–549 K
Hall symbol: P 2yb	Mo Kα radiation λ = 0.71073 Å
a = 12.345 (3) Å	Cell parameters from 2029 reflections
b = 9.6763 (19) Å	θ = 2.7–20.6º
c = 13.268 (3) Å	µ = 0.26 mm−1
β = 115.00 (3)º	T = 296 (2) K
V = 1436.4 (5) Å3	Block, colorless
Z = 2	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3736 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 173(2) K	θmax = 25.0º
ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.926, Tmax = 0.950	k = −5→11
7509 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0287P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.14 e Å−3
3736 reflections	Δρmin = −0.15 e Å−3
344 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1031 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (6)
Secondary atom site location: difference Fourier map

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	0.82566 (10)	0.19017 (14)	0.84787 (9)	0.1067 (4)
Cl2	0.93108 (9)	−0.23669 (14)	0.26803 (10)	0.1163 (4)
N4	0.3040 (2)	0.0470 (3)	−0.03488 (19)	0.0535 (7)
O2	0.4646 (2)	0.0216 (3)	−0.19685 (16)	0.0699 (7)
N2	0.2426 (2)	0.4329 (3)	0.4064 (2)	0.0591 (7)
C3	0.3001 (3)	0.2513 (3)	0.1935 (2)	0.0518 (8)
H3A	0.3772	0.2901	0.2141	0.062*
C2	0.2559 (3)	0.1586 (3)	0.1053 (2)	0.0472 (8)
N5	0.3995 (2)	0.0474 (3)	−0.06575 (19)	0.0520 (7)
N1	0.0772 (2)	0.1372 (3)	0.1322 (2)	0.0595 (7)
C8	0.2922 (3)	0.3870 (3)	0.3447 (2)	0.0511 (8)
N3	0.3251 (2)	0.5240 (3)	0.4848 (2)	0.0588 (7)
C21	0.5046 (3)	0.1276 (3)	0.0106 (2)	0.0498 (8)
H21A	0.5260	0.1990	−0.0324	0.060*
C1	0.1420 (3)	0.1018 (3)	0.0771 (2)	0.0533 (8)
C4	0.2348 (3)	0.2885 (3)	0.2519 (2)	0.0501 (8)
C19	0.3333 (3)	0.1291 (3)	0.0493 (2)	0.0474 (8)
C20	0.4534 (2)	0.1978 (3)	0.0844 (2)	0.0503 (8)
H20A	0.5048	0.1814	0.1641	0.060*
H20B	0.4447	0.2986	0.0705	0.060*
C13	0.5391 (3)	0.4494 (3)	0.5838 (3)	0.0547 (8)
C24	0.6109 (2)	0.0369 (3)	0.0729 (2)	0.0475 (8)
O1	0.3715 (2)	0.6813 (3)	0.6201 (2)	0.0844 (8)
C7	0.0821 (3)	−0.0002 (4)	−0.0160 (3)	0.0701 (10)
H7A	0.0072	−0.0321	−0.0150	0.105*
H7B	0.1351	−0.0793	−0.0061	0.105*
H7C	0.0650	0.0446	−0.0874	0.105*
C29	0.6086 (3)	−0.0608 (4)	0.1481 (3)	0.0580 (9)
H29A	0.5379	−0.0706	0.1593	0.070*
C11	0.2948 (4)	0.6055 (4)	0.5529 (3)	0.0677 (10)
C9	0.4157 (3)	0.4450 (3)	0.3751 (2)	0.0564 (9)
H9A	0.4160	0.5088	0.3169	0.068*
H9B	0.4743	0.3702	0.3860	0.068*
C18	0.5107 (3)	0.3598 (4)	0.6500 (3)	0.0598 (9)
H18A	0.4298	0.3507	0.6388	0.072*
C10	0.4435 (3)	0.5226 (4)	0.4848 (2)	0.0578 (9)
H10A	0.4694	0.6193	0.4797	0.069*
C25	0.7154 (3)	0.0477 (4)	0.0600 (3)	0.0642 (10)
H25A	0.7208	0.1143	0.0097	0.077*
C17	0.5992 (3)	0.2823 (4)	0.7333 (3)	0.0667 (9)
H17A	0.5787	0.2220	0.7790	0.080*
C22	0.3836 (3)	0.0014 (3)	−0.1681 (3)	0.0563 (9)
C28	0.7057 (3)	−0.1451 (4)	0.2079 (3)	0.0667 (10)
H28A	0.7016	−0.2112	0.2591	0.080*
C14	0.6579 (3)	0.4611 (4)	0.6040 (3)	0.0742 (11)
H14A	0.6801	0.5241	0.5611	0.089*
C27	0.8074 (3)	−0.1310 (4)	0.1916 (3)	0.0684 (10)
C6	0.0396 (3)	0.2566 (5)	0.2730 (3)	0.0917 (14)
H6A	−0.0334	0.2013	0.2372	0.138*
H6B	0.0187	0.3549	0.2660	0.138*
H6C	0.0800	0.2318	0.3519	0.138*
C5	0.1217 (3)	0.2283 (3)	0.2175 (3)	0.0572 (9)
C16	0.7161 (3)	0.2940 (4)	0.7486 (3)	0.0690 (10)
C26	0.8133 (3)	−0.0363 (5)	0.1185 (3)	0.0753 (11)
H26A	0.8842	−0.0276	0.1074	0.090*
C15	0.7466 (3)	0.3822 (5)	0.6863 (3)	0.0814 (12)
H15A	0.8277	0.3908	0.6980	0.098*
C12	0.1685 (3)	0.5944 (5)	0.5398 (3)	0.0878 (12)
H12A	0.1567	0.6570	0.5924	0.132*
H12B	0.1525	0.4992	0.5548	0.132*
H12C	0.1136	0.6197	0.4637	0.132*
C23	0.2705 (3)	−0.0739 (4)	−0.2390 (3)	0.0778 (11)
H23A	0.2731	−0.1018	−0.3089	0.117*
H23B	0.2019	−0.0129	−0.2548	0.117*
H23C	0.2629	−0.1561	−0.1994	0.117*

	U11	U22	U33	U12	U13	U23
Cl1	0.0941 (8)	0.1130 (9)	0.1006 (8)	0.0245 (7)	0.0290 (6)	0.0137 (7)
Cl2	0.0693 (7)	0.1272 (11)	0.1354 (10)	0.0249 (7)	0.0267 (6)	0.0115 (8)
N4	0.0520 (16)	0.065 (2)	0.0518 (16)	−0.0009 (14)	0.0295 (13)	−0.0093 (15)
O2	0.0865 (17)	0.0762 (18)	0.0682 (15)	−0.0036 (13)	0.0531 (14)	−0.0109 (13)
N2	0.0685 (18)	0.064 (2)	0.0524 (16)	0.0096 (16)	0.0333 (15)	−0.0045 (15)
C3	0.0518 (18)	0.058 (2)	0.0517 (18)	−0.0006 (17)	0.0278 (16)	−0.0058 (17)
C2	0.0498 (18)	0.051 (2)	0.0464 (18)	0.0020 (15)	0.0262 (16)	−0.0037 (16)
N5	0.0536 (16)	0.0614 (19)	0.0479 (15)	−0.0026 (14)	0.0282 (13)	−0.0081 (14)
N1	0.0504 (16)	0.070 (2)	0.0659 (18)	−0.0028 (14)	0.0323 (15)	−0.0081 (16)
C8	0.063 (2)	0.051 (2)	0.0437 (18)	0.0075 (17)	0.0274 (17)	−0.0005 (16)
N3	0.0655 (18)	0.062 (2)	0.0556 (16)	0.0036 (15)	0.0319 (15)	−0.0152 (15)
C21	0.0572 (19)	0.050 (2)	0.0508 (18)	−0.0131 (17)	0.0315 (16)	−0.0076 (17)
C1	0.0519 (19)	0.059 (2)	0.0488 (19)	−0.0016 (17)	0.0213 (16)	−0.0033 (17)
C4	0.060 (2)	0.050 (2)	0.0499 (19)	0.0034 (17)	0.0320 (16)	0.0011 (17)
C19	0.0526 (19)	0.047 (2)	0.0435 (18)	0.0018 (16)	0.0214 (15)	−0.0054 (16)
C20	0.0570 (19)	0.051 (2)	0.0503 (18)	−0.0052 (16)	0.0297 (16)	−0.0076 (17)
C13	0.067 (2)	0.051 (2)	0.054 (2)	−0.0064 (18)	0.0341 (18)	−0.0127 (17)
C24	0.0502 (19)	0.049 (2)	0.0514 (19)	−0.0069 (17)	0.0292 (16)	−0.0083 (17)
O1	0.109 (2)	0.0778 (19)	0.0720 (17)	0.0029 (17)	0.0441 (16)	−0.0235 (16)
C7	0.065 (2)	0.077 (3)	0.076 (2)	−0.013 (2)	0.037 (2)	−0.018 (2)
C29	0.052 (2)	0.063 (2)	0.067 (2)	−0.0037 (18)	0.0330 (18)	−0.006 (2)
C11	0.084 (3)	0.066 (3)	0.057 (2)	0.021 (2)	0.034 (2)	−0.002 (2)
C9	0.075 (2)	0.052 (2)	0.052 (2)	−0.0078 (18)	0.0363 (18)	−0.0114 (17)
C18	0.064 (2)	0.066 (3)	0.061 (2)	−0.0023 (19)	0.0382 (19)	−0.0068 (19)
C10	0.071 (2)	0.055 (2)	0.056 (2)	−0.0092 (19)	0.0355 (19)	−0.0090 (18)
C25	0.066 (2)	0.070 (3)	0.072 (2)	−0.008 (2)	0.043 (2)	−0.001 (2)
C17	0.085 (3)	0.066 (3)	0.066 (2)	0.004 (2)	0.047 (2)	0.001 (2)
C22	0.067 (2)	0.054 (2)	0.052 (2)	0.0047 (18)	0.0293 (19)	−0.0077 (17)
C28	0.070 (2)	0.069 (3)	0.071 (2)	−0.002 (2)	0.039 (2)	0.002 (2)
C14	0.079 (3)	0.078 (3)	0.080 (3)	−0.020 (2)	0.047 (2)	−0.001 (2)
C27	0.051 (2)	0.076 (3)	0.073 (2)	0.003 (2)	0.0206 (19)	−0.009 (2)
C6	0.075 (2)	0.126 (4)	0.101 (3)	−0.013 (3)	0.063 (2)	−0.034 (3)
C5	0.053 (2)	0.068 (3)	0.059 (2)	0.0039 (18)	0.0314 (17)	−0.0082 (19)
C16	0.069 (2)	0.072 (3)	0.062 (2)	0.003 (2)	0.025 (2)	−0.006 (2)
C26	0.054 (2)	0.092 (3)	0.092 (3)	−0.007 (2)	0.042 (2)	−0.010 (2)
C15	0.064 (3)	0.090 (3)	0.095 (3)	−0.007 (2)	0.039 (2)	0.005 (3)
C12	0.087 (3)	0.101 (3)	0.082 (3)	0.027 (2)	0.042 (2)	−0.015 (2)
C23	0.076 (2)	0.088 (3)	0.069 (2)	−0.005 (2)	0.030 (2)	−0.032 (2)

Cl1—C16	1.752 (4)	C7—H7B	0.9800
Cl2—C27	1.760 (4)	C7—H7C	0.9800
N4—C19	1.291 (3)	C29—C28	1.389 (4)
N4—N5	1.401 (3)	C29—H29A	0.9500
O2—C22	1.227 (3)	C11—C12	1.498 (5)
N2—C8	1.291 (3)	C9—C10	1.543 (4)
N2—N3	1.415 (3)	C9—H9A	0.9900
C3—C4	1.382 (4)	C9—H9B	0.9900
C3—C2	1.390 (4)	C18—C17	1.399 (4)
C3—H3A	0.9500	C18—H18A	0.9500
C2—C1	1.406 (4)	C10—H10A	1.0000
C2—C19	1.465 (4)	C25—C26	1.390 (5)
N5—C22	1.362 (4)	C25—H25A	0.9500
N5—C21	1.484 (3)	C17—C16	1.374 (4)
N1—C1	1.336 (3)	C17—H17A	0.9500
N1—C5	1.355 (4)	C22—C23	1.502 (4)
C8—C4	1.480 (4)	C28—C27	1.367 (4)
C8—C9	1.511 (4)	C28—H28A	0.9500
N3—C11	1.365 (4)	C14—C15	1.400 (5)
N3—C10	1.460 (4)	C14—H14A	0.9500
C21—C24	1.502 (4)	C27—C26	1.359 (5)
C21—C20	1.530 (4)	C6—C5	1.509 (4)
C21—H21A	1.0000	C6—H6A	0.9800
C1—C7	1.508 (4)	C6—H6B	0.9800
C4—C5	1.399 (4)	C6—H6C	0.9800
C19—C20	1.508 (4)	C16—C15	1.348 (5)
C20—H20A	0.9900	C26—H26A	0.9500
C20—H20B	0.9900	C15—H15A	0.9500
C13—C18	1.381 (4)	C12—H12A	0.9800
C13—C14	1.380 (4)	C12—H12B	0.9800
C13—C10	1.519 (4)	C12—H12C	0.9800
C24—C25	1.376 (4)	C23—H23A	0.9800
C24—C29	1.384 (4)	C23—H23B	0.9800
O1—C11	1.231 (4)	C23—H23C	0.9800
C7—H7A	0.9800
C19—N4—N5	106.8 (2)	C8—C9—H9B	111.1
C8—N2—N3	107.0 (3)	C10—C9—H9B	111.1
C4—C3—C2	121.8 (3)	H9A—C9—H9B	109.1
C4—C3—H3A	119.1	C13—C18—C17	121.0 (3)
C2—C3—H3A	119.1	C13—C18—H18A	119.5
C3—C2—C1	117.9 (2)	C17—C18—H18A	119.5
C3—C2—C19	116.4 (3)	N3—C10—C13	114.6 (3)
C1—C2—C19	125.6 (3)	N3—C10—C9	100.4 (2)
C22—N5—N4	120.4 (3)	C13—C10—C9	111.7 (3)
C22—N5—C21	124.5 (3)	N3—C10—H10A	109.9
N4—N5—C21	113.8 (2)	C13—C10—H10A	109.9
C1—N1—C5	119.9 (3)	C9—C10—H10A	109.9
N2—C8—C4	124.1 (3)	C24—C25—C26	121.8 (3)
N2—C8—C9	113.5 (3)	C24—C25—H25A	119.1
C4—C8—C9	122.4 (3)	C26—C25—H25A	119.1
C11—N3—N2	122.1 (3)	C16—C17—C18	119.6 (3)
C11—N3—C10	124.0 (3)	C16—C17—H17A	120.2
N2—N3—C10	113.8 (2)	C18—C17—H17A	120.2
N5—C21—C24	112.2 (2)	O2—C22—N5	117.7 (3)
N5—C21—C20	101.0 (2)	O2—C22—C23	123.1 (3)
C24—C21—C20	114.1 (2)	N5—C22—C23	119.1 (3)
N5—C21—H21A	109.7	C27—C28—C29	118.7 (3)
C24—C21—H21A	109.7	C27—C28—H28A	120.7
C20—C21—H21A	109.7	C29—C28—H28A	120.7
N1—C1—C2	121.2 (3)	C13—C14—C15	121.6 (3)
N1—C1—C7	114.6 (3)	C13—C14—H14A	119.2
C2—C1—C7	124.2 (3)	C15—C14—H14A	119.2
C3—C4—C5	116.5 (3)	C26—C27—C28	120.7 (3)
C3—C4—C8	116.6 (3)	C26—C27—Cl2	120.5 (3)
C5—C4—C8	126.9 (3)	C28—C27—Cl2	118.8 (3)
N4—C19—C2	123.7 (3)	C5—C6—H6A	109.5
N4—C19—C20	114.7 (2)	C5—C6—H6B	109.5
C2—C19—C20	121.6 (3)	H6A—C6—H6B	109.5
C19—C20—C21	103.0 (2)	C5—C6—H6C	109.5
C19—C20—H20A	111.2	H6A—C6—H6C	109.5
C21—C20—H20A	111.2	H6B—C6—H6C	109.5
C19—C20—H20B	111.2	N1—C5—C4	122.7 (3)
C21—C20—H20B	111.2	N1—C5—C6	114.0 (3)
H20A—C20—H20B	109.1	C4—C5—C6	123.3 (3)
C18—C13—C14	117.5 (3)	C15—C16—C17	120.6 (3)
C18—C13—C10	121.9 (3)	C15—C16—Cl1	119.8 (3)
C14—C13—C10	120.3 (3)	C17—C16—Cl1	119.5 (3)
C25—C24—C29	116.6 (3)	C27—C26—C25	119.8 (3)
C25—C24—C21	122.3 (3)	C27—C26—H26A	120.1
C29—C24—C21	121.1 (3)	C25—C26—H26A	120.1
C1—C7—H7A	109.5	C16—C15—C14	119.6 (3)
C1—C7—H7B	109.5	C16—C15—H15A	120.2
H7A—C7—H7B	109.5	C14—C15—H15A	120.2
C1—C7—H7C	109.5	C11—C12—H12A	109.5
H7A—C7—H7C	109.5	C11—C12—H12B	109.5
H7B—C7—H7C	109.5	H12A—C12—H12B	109.5
C28—C29—C24	122.5 (3)	C11—C12—H12C	109.5
C28—C29—H29A	118.7	H12A—C12—H12C	109.5
C24—C29—H29A	118.7	H12B—C12—H12C	109.5
O1—C11—N3	118.8 (3)	C22—C23—H23A	109.5
O1—C11—C12	124.8 (3)	C22—C23—H23B	109.5
N3—C11—C12	116.4 (3)	H23A—C23—H23B	109.5
C8—C9—C10	103.2 (2)	C22—C23—H23C	109.5
C8—C9—H9A	111.1	H23A—C23—H23C	109.5
C10—C9—H9A	111.1	H23B—C23—H23C	109.5
C4—C3—C2—C1	−0.5 (5)	N2—N3—C11—C12	−0.4 (5)
C4—C3—C2—C19	179.3 (3)	C10—N3—C11—C12	179.1 (3)
C19—N4—N5—C22	−162.3 (3)	N2—C8—C9—C10	8.9 (3)
C19—N4—N5—C21	5.3 (3)	C4—C8—C9—C10	−171.8 (3)
N3—N2—C8—C4	−179.9 (3)	C14—C13—C18—C17	−1.0 (5)
N3—N2—C8—C9	−0.6 (3)	C10—C13—C18—C17	173.1 (3)
C8—N2—N3—C11	170.7 (3)	C11—N3—C10—C13	74.2 (4)
C8—N2—N3—C10	−8.9 (3)	N2—N3—C10—C13	−106.2 (3)
C22—N5—C21—C24	−79.9 (4)	C11—N3—C10—C9	−165.9 (3)
N4—N5—C21—C24	113.0 (3)	N2—N3—C10—C9	13.7 (3)
C22—N5—C21—C20	158.2 (3)	C18—C13—C10—N3	17.2 (4)
N4—N5—C21—C20	−8.9 (3)	C14—C13—C10—N3	−168.8 (3)
C5—N1—C1—C2	−0.6 (5)	C18—C13—C10—C9	−96.1 (3)
C5—N1—C1—C7	−179.9 (3)	C14—C13—C10—C9	77.8 (4)
C3—C2—C1—N1	1.0 (4)	C8—C9—C10—N3	−12.5 (3)
C19—C2—C1—N1	−178.8 (3)	C8—C9—C10—C13	109.4 (3)
C3—C2—C1—C7	−179.9 (3)	C29—C24—C25—C26	0.7 (5)
C19—C2—C1—C7	0.4 (5)	C21—C24—C25—C26	179.7 (3)
C2—C3—C4—C5	−0.2 (5)	C13—C18—C17—C16	−0.9 (5)
C2—C3—C4—C8	179.4 (3)	N4—N5—C22—O2	170.1 (3)
N2—C8—C4—C3	179.2 (3)	C21—N5—C22—O2	3.8 (5)
C9—C8—C4—C3	0.0 (4)	N4—N5—C22—C23	−11.4 (4)
N2—C8—C4—C5	−1.2 (5)	C21—N5—C22—C23	−177.6 (3)
C9—C8—C4—C5	179.6 (3)	C24—C29—C28—C27	−0.1 (5)
N5—N4—C19—C2	179.1 (3)	C18—C13—C14—C15	1.9 (5)
N5—N4—C19—C20	1.1 (3)	C10—C13—C14—C15	−172.3 (3)
C3—C2—C19—N4	−178.9 (3)	C29—C28—C27—C26	0.1 (5)
C1—C2—C19—N4	0.9 (5)	C29—C28—C27—Cl2	179.5 (3)
C3—C2—C19—C20	−1.1 (4)	C1—N1—C5—C4	−0.2 (5)
C1—C2—C19—C20	178.7 (3)	C1—N1—C5—C6	−179.0 (3)
N4—C19—C20—C21	−6.5 (3)	C3—C4—C5—N1	0.6 (5)
C2—C19—C20—C21	175.5 (3)	C8—C4—C5—N1	−179.0 (3)
N5—C21—C20—C19	8.4 (3)	C3—C4—C5—C6	179.3 (3)
C24—C21—C20—C19	−112.2 (3)	C8—C4—C5—C6	−0.3 (5)
N5—C21—C24—C25	116.5 (3)	C18—C17—C16—C15	1.9 (5)
C20—C21—C24—C25	−129.5 (3)	C18—C17—C16—Cl1	−176.6 (3)
N5—C21—C24—C29	−64.7 (4)	C28—C27—C26—C25	0.3 (6)
C20—C21—C24—C29	49.4 (4)	Cl2—C27—C26—C25	−179.1 (3)
C25—C24—C29—C28	−0.3 (5)	C24—C25—C26—C27	−0.8 (5)
C21—C24—C29—C28	−179.3 (3)	C17—C16—C15—C14	−1.0 (6)
N2—N3—C11—O1	179.2 (3)	Cl1—C16—C15—C14	177.5 (3)
C10—N3—C11—O1	−1.3 (5)	C13—C14—C15—C16	−1.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.99	2.59	3.358 (3)	135
C17—H17A···O2ii	0.95	2.50	3.359 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.99	2.59	3.358 (3)	135
C17—H17A⋯O2ii	0.95	2.50	3.359 (4)	151

Symmetry codes: (i) ; (ii) .