Crystal structure of (E)-N-[(2-chloro-6-meth-oxy-quinolin-3-yl)methyl-idene]-9-ethyl-9H-carbazol-3-amine.

In the title compound, C25H20ClN3O, the C=N bond of the central imine group adopts an E conformation. The mean planes through the essentially planar carbazole [maximum deviation = 0.052 (2)Å] and quinoline [maximum deviation = 0.050 (2) Å] ring systems form a dihedral angle of 50.2 (1)°. In the crystal, mol-ecules are linked by C-H⋯π and π-π inter-actions [centroid-centroid distances ranging from 3.635 (2) to 3.739 (2) Å], forming a three-dimensional supra-molecular network.

Chemical context

It has been reported that carbazole derivatives possess various biological activities, such as anti­tumor (Itoigawa et al., 2000 ▸), anti-oxidative (Tachibana et al., 2001 ▸), anti-inflammatory and anti­mutagenic (Ramsewak et al., 1999 ▸). Carbazole derivatives also exhibit electroactivity and luminescence properties and are considered to be potential candidates for electronic devices such as colour displays, organic semiconductor lasers and solar cells (Friend et al., 1999 ▸). These compounds are thermally and photochemically stable, which makes them useful materials for technological applications: for instance, the carbazole ring is easily funtionalized and covalently linked to other mol­ecules (Díaz et al., 2002 ▸). This enables its use as a convenient building block for the design and synthesis of mol­ecular glasses, which are widely studied as components of electroactive and photoactive materials (Zhang et al., 2004 ▸). Quinoline derivatives are known to possess a variety of biological properties such as anti­malarial and anti­viral activity (Cunico et al., 2006 ▸; Hartline et al., 2005 ▸). Against this background, and in order to obtain detailed information on its mol­ecular conformation in the solid state, the crystal structure of the title compound has been determined.

Structural commentary

Fig. 1 ▸. shows a displacement ellipsoid plot of (I), with the atom-numbering scheme. The C=N bond of the central imine group adopts an E conformation. The mean planes through the essentially planar carbazole [N1/C1–C12; maximum deviation = 0.052 (2) Å for atom C12] and quinoline [N3/C16–C24; maximum deviation = 0.050 (2) Å for atom C16] ring systems form a dihedral angle of 50.2 (1)°. The sum of the bond angles around N1 (360.05°) of the pyrrole ring is in accordance with sp 2 hybridization. Atom Cl1 deviates from the plane of the attached quinoline ring system by 0.100 (1) Å. The geometric parameters of the title mol­ecule agree well with those reported for similar structures (Murugavel et al., 2009 ▸; Archana et al., 2011 ▸).

Figure 1

Mol­ecular structure of the title compound showing displacement ellipsoids at the 30% probability level. H atoms are drawn as a small spheres of arbitrary radii.

Supra­molecular features

In the crystal, mol­ecules are linked by two C—H⋯π inter­actions; the first one between the benzene H atom of the carbazole ring system and the benzene ring of an adjacent mol­ecule, with a C1—H1⋯Cg1i and the second one between the benzene H atom of the carbazole ring system and the benzene ring of an adjacent mol­ecule, with a C7—H7⋯Cg2ii. The mol­ecules are further linked by π–π inter­actions with Cg3–Cg3iii, Cg3–Cg2iii, Cg2–Cg3iii, Cg4–Cg1iv and Cg1–Cg4iv separations of 3.735 (2), 3.739 (2), 3.739 (2), 3.635 (2) and 3.635 (2) Å, respectively, forming a three-dimensional supra­molecular network (Table 1 ▸ and Fig. 2 ▸; Cg1, Cg2, Cg3 and Cg4 are the centroids of C18–C23 benzene ring, the C1–C3/C10–C12 benzene ring, the N1/C3/C4/C9/C10 pyrrole ring and the N3/C16–C18/C23/C24 pyridine ring, respectively; symmetry codes: (i) −x, −y, 1 − z; (ii) 1 − x,  + y,  − z; (iii) 1 − x, −y, 1 − z and (iv) −x, 1 − y, 1 − z).

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C18C23 and C1C3/C10C12 benzene rings, respectively.

DHA	DH	HA	D A	DHA
C1H1Cg1i	0.93	2.87	3.718(3)	152
C7H7Cg2ii	0.93	2.97	3.688(2)	145

Symmetry codes: (i) ; (ii) .

Figure 2

Part of the crystal structure of the title compound showing the C—H⋯π and π–π inter­actions, which lead to the formation of a three-dimensional supra­molecular network. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Cg1, Cg2, Cg3 and Cg4 are the centroids of the C18–C23 benzene ring, the C1–C3/C10–C12 benzene ring, the N1/C3/C4/C9/C10 pyrrole ring and the N3/C16–C18/C23/C24 pyridine ring, respectively.

Synthesis and crystallization

A 25 ml round-bottom flask was charged with dimedone (1 mmol), 2-chloro-6-meth­oxy­quinoline-3-carbaldehyde (1 mmol) 9-ethyl-9H-carbazol-3-amine (1 mmol) and sulfated SnO2-fly ash catalyst (50 mg) in water (15 ml) and was refluxed at 353 K for 5–10 minutes. The completion of the reaction was monitored by TLC (ethyl acetate and hexane as an eluent 20%). After completion, the reaction mixture was cooled to ambient temperature. Then di­chloro­methane (20 ml) was added and the organic layer filtered, dried on anhydrous Na2SO4 and the solvent removed using a rotary evaporator. The crude product was purified by column chromatography on silica gel (200 mesh) with hexane and ethyl acetate (4:1) as eluent to afford the title compound in good yield (10%). Red blocks suitable for X-ray diffraction analysis were obtained by recrystallization from di­chloro­methane solution at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were positioned geom­etrically and constrained to ride on their parent atom with C—H = 0.93–0.97 Å and with U iso(H)=1.5U eq for methyl H atoms and 1.2U eq(C) for other H atoms.

Table 2

Experimental details

Crystal data
Chemical formula	C25H20ClN3O
M r	413.89
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	293
a, b, c ()	15.060(3), 8.8231(15), 15.332(3)
()	93.344(3)
V (3)	2033.9(6)
Z	4
Radiation type	Mo K
(mm1)	0.21
Crystal size (mm)	0.24 0.21 0.16
Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 ▸)
T min, T max	0.951, 0.967
No. of measured, independent and observed [I > 2(I)] reflections	20538, 4023, 2340
R int	0.056
(sin /)max (1)	0.620
Refinement
R[F 2 > 2(F 2)], wR(F 2), S	0.051, 0.133, 1.01
No. of reflections	4023
No. of parameters	273
H-atom treatment	H-atom parameters constrained
max, min (e 3)	0.24, 0.14

Computer programs: SMART and SAINT (Bruker, 2002 ▸), SHELXS97 and SHELXL97 (Sheldrick, 2008 ▸), ORTEP-3 for Windows (Farrugia (1997 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015005794/hb7384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005794/hb7384Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015005794/hb7384Isup3.cml

CCDC reference: 1027676

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H20ClN3O	F(000) = 864
Mr = 413.89	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4051 reflections
a = 15.060 (3) Å	θ = 1.4–26.1°
b = 8.8231 (15) Å	µ = 0.21 mm−1
c = 15.332 (3) Å	T = 293 K
β = 93.344 (3)°	Block, red
V = 2033.9 (6) Å3	0.24 × 0.21 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	4023 independent reflections
Radiation source: fine-focus sealed tube	2340 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 26.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.951, Tmax = 0.967	k = −10→10
20538 measured reflections	l = −18→18

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) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.145P] where P = (Fo2 + 2Fc2)/3
4023 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.06066 (5)	0.06058 (9)	0.30880 (4)	0.0824 (3)
C10	0.43767 (14)	0.0240 (2)	0.62074 (13)	0.0455 (6)
C11	0.35381 (15)	0.0892 (3)	0.61516 (14)	0.0481 (6)
H11	0.3441	0.1814	0.6424	0.058*
N2	0.20216 (12)	0.0956 (2)	0.55982 (12)	0.0541 (5)
O1	−0.20036 (11)	0.5826 (2)	0.63150 (12)	0.0760 (6)
C23	−0.08229 (15)	0.3293 (3)	0.44161 (15)	0.0531 (6)
N3	−0.04814 (13)	0.2485 (2)	0.37581 (12)	0.0585 (5)
N1	0.53829 (13)	−0.1591 (2)	0.59420 (13)	0.0562 (5)
C9	0.52392 (15)	0.0703 (3)	0.65834 (14)	0.0484 (6)
C3	0.45006 (15)	−0.1178 (3)	0.58178 (15)	0.0491 (6)
C12	0.28459 (15)	0.0167 (3)	0.56899 (14)	0.0497 (6)
C4	0.58357 (16)	−0.0465 (3)	0.64053 (15)	0.0524 (6)
C2	0.38021 (16)	−0.1946 (3)	0.53925 (15)	0.0566 (6)
H2	0.3885	−0.2902	0.5155	0.068*
C24	0.02130 (16)	0.1662 (3)	0.39528 (15)	0.0555 (6)
C18	−0.04726 (14)	0.3209 (3)	0.52873 (15)	0.0494 (6)
C19	−0.08694 (15)	0.4038 (3)	0.59474 (15)	0.0576 (6)
H19	−0.0646	0.3964	0.6524	0.069*
C16	0.06697 (14)	0.1538 (3)	0.47843 (15)	0.0509 (6)
C20	−0.15802 (16)	0.4946 (3)	0.57397 (16)	0.0583 (7)
C1	0.29845 (16)	−0.1263 (3)	0.53286 (15)	0.0569 (6)
H1	0.2510	−0.1762	0.5038	0.068*
C22	−0.15569 (16)	0.4262 (3)	0.42313 (17)	0.0634 (7)
H22	−0.1796	0.4345	0.3660	0.076*
C8	0.55487 (16)	0.1987 (3)	0.70283 (15)	0.0590 (7)
H8	0.5159	0.2760	0.7161	0.071*
C17	0.02964 (14)	0.2319 (3)	0.54418 (15)	0.0534 (6)
H17	0.0558	0.2260	0.6006	0.064*
C15	0.15054 (15)	0.0715 (3)	0.49281 (16)	0.0566 (6)
H15	0.1664	−0.0001	0.4520	0.068*
C6	0.70181 (18)	0.0939 (4)	0.70840 (17)	0.0737 (8)
H6	0.7618	0.1043	0.7252	0.088*
C13	0.57753 (17)	−0.2968 (3)	0.56101 (16)	0.0649 (7)
H13A	0.6399	−0.2785	0.5522	0.078*
H13B	0.5483	−0.3215	0.5048	0.078*
C21	−0.19161 (16)	0.5068 (3)	0.48695 (17)	0.0635 (7)
H21	−0.2392	0.5712	0.4731	0.076*
C5	0.67368 (17)	−0.0363 (3)	0.66605 (16)	0.0645 (7)
H5	0.7131	−0.1142	0.6549	0.077*
C7	0.64419 (17)	0.2099 (3)	0.72704 (17)	0.0691 (7)
H7	0.6658	0.2960	0.7561	0.083*
C25	−0.17246 (19)	0.5688 (4)	0.72159 (18)	0.0863 (9)
H25A	−0.1805	0.4660	0.7402	0.129*
H25B	−0.2073	0.6352	0.7555	0.129*
H25C	−0.1108	0.5957	0.7297	0.129*
C14	0.5698 (2)	−0.4287 (3)	0.62109 (19)	0.0851 (9)
H14A	0.6001	−0.4060	0.6764	0.128*
H14B	0.5963	−0.5164	0.5961	0.128*
H14C	0.5082	−0.4485	0.6293	0.128*

	U11	U22	U33	U12	U13	U23
Cl1	0.0740 (5)	0.1134 (6)	0.0590 (4)	0.0144 (4)	−0.0030 (3)	−0.0197 (4)
C10	0.0480 (14)	0.0460 (14)	0.0432 (13)	0.0059 (11)	0.0087 (11)	0.0064 (11)
C11	0.0540 (15)	0.0480 (14)	0.0428 (13)	0.0056 (12)	0.0066 (11)	0.0009 (11)
N2	0.0459 (12)	0.0633 (13)	0.0525 (12)	0.0033 (10)	−0.0018 (10)	0.0017 (10)
O1	0.0624 (11)	0.0998 (14)	0.0659 (12)	0.0237 (10)	0.0059 (9)	−0.0051 (11)
C23	0.0431 (14)	0.0651 (16)	0.0504 (14)	−0.0048 (12)	−0.0039 (11)	0.0000 (13)
N3	0.0499 (12)	0.0747 (14)	0.0498 (12)	0.0013 (11)	−0.0053 (10)	−0.0042 (11)
N1	0.0583 (13)	0.0539 (13)	0.0571 (13)	0.0147 (11)	0.0091 (10)	0.0023 (10)
C9	0.0499 (14)	0.0558 (15)	0.0401 (13)	0.0044 (12)	0.0069 (11)	0.0048 (11)
C3	0.0498 (15)	0.0504 (14)	0.0479 (13)	0.0068 (12)	0.0084 (11)	0.0065 (11)
C12	0.0471 (14)	0.0561 (15)	0.0460 (13)	0.0032 (12)	0.0035 (11)	0.0032 (12)
C4	0.0533 (15)	0.0620 (16)	0.0423 (13)	0.0087 (14)	0.0051 (11)	0.0084 (12)
C2	0.0667 (17)	0.0448 (14)	0.0584 (15)	0.0052 (13)	0.0043 (13)	−0.0011 (12)
C24	0.0496 (15)	0.0677 (17)	0.0495 (14)	−0.0050 (13)	0.0039 (12)	−0.0042 (12)
C18	0.0382 (13)	0.0596 (15)	0.0500 (14)	−0.0034 (11)	−0.0004 (11)	0.0039 (12)
C19	0.0478 (14)	0.0759 (17)	0.0487 (14)	0.0004 (13)	0.0000 (11)	0.0013 (13)
C16	0.0425 (13)	0.0601 (15)	0.0496 (14)	−0.0034 (12)	−0.0005 (11)	0.0004 (12)
C20	0.0449 (15)	0.0738 (17)	0.0562 (16)	0.0009 (13)	0.0029 (12)	−0.0001 (13)
C1	0.0579 (16)	0.0567 (16)	0.0559 (15)	−0.0036 (13)	0.0012 (12)	−0.0006 (12)
C22	0.0516 (15)	0.0836 (19)	0.0533 (15)	0.0021 (14)	−0.0123 (12)	0.0033 (14)
C8	0.0562 (16)	0.0674 (17)	0.0535 (15)	0.0046 (13)	0.0048 (12)	−0.0007 (13)
C17	0.0450 (14)	0.0681 (16)	0.0463 (14)	−0.0043 (13)	−0.0052 (11)	0.0028 (12)
C15	0.0510 (15)	0.0649 (16)	0.0542 (15)	0.0012 (13)	0.0058 (12)	−0.0031 (13)
C6	0.0528 (16)	0.111 (2)	0.0561 (16)	0.0032 (17)	−0.0070 (13)	−0.0003 (17)
C13	0.0713 (17)	0.0633 (16)	0.0612 (16)	0.0199 (14)	0.0127 (14)	−0.0010 (14)
C21	0.0484 (15)	0.0732 (17)	0.0678 (18)	0.0049 (13)	−0.0062 (13)	0.0035 (15)
C5	0.0543 (16)	0.083 (2)	0.0564 (16)	0.0182 (15)	0.0018 (13)	0.0085 (15)
C7	0.0610 (18)	0.083 (2)	0.0625 (17)	0.0000 (16)	−0.0006 (14)	−0.0098 (14)
C25	0.083 (2)	0.117 (3)	0.0600 (18)	0.0211 (18)	0.0132 (16)	−0.0040 (17)
C14	0.117 (3)	0.0603 (18)	0.080 (2)	0.0244 (17)	0.0234 (18)	0.0072 (15)

Cl1—C24	1.752 (2)	C19—C20	1.360 (3)
C10—C11	1.386 (3)	C19—H19	0.9300
C10—C3	1.404 (3)	C16—C17	1.369 (3)
C10—C9	1.449 (3)	C16—C15	1.458 (3)
C11—C12	1.382 (3)	C20—C21	1.403 (3)
C11—H11	0.9300	C1—H1	0.9300
N2—C15	1.269 (3)	C22—C21	1.348 (3)
N2—C12	1.423 (3)	C22—H22	0.9300
O1—C20	1.361 (3)	C8—C7	1.378 (3)
O1—C25	1.425 (3)	C8—H8	0.9300
C23—N3	1.361 (3)	C17—H17	0.9300
C23—C18	1.409 (3)	C15—H15	0.9300
C23—C22	1.413 (3)	C6—C5	1.374 (4)
N3—C24	1.294 (3)	C6—C7	1.382 (4)
N1—C4	1.378 (3)	C6—H6	0.9300
N1—C3	1.380 (3)	C13—C14	1.493 (3)
N1—C13	1.456 (3)	C13—H13A	0.9700
C9—C8	1.389 (3)	C13—H13B	0.9700
C9—C4	1.404 (3)	C21—H21	0.9300
C3—C2	1.382 (3)	C5—H5	0.9300
C12—C1	1.399 (3)	C7—H7	0.9300
C4—C5	1.393 (3)	C25—H25A	0.9600
C2—C1	1.369 (3)	C25—H25B	0.9600
C2—H2	0.9300	C25—H25C	0.9600
C24—C16	1.417 (3)	C14—H14A	0.9600
C18—C17	1.408 (3)	C14—H14B	0.9600
C18—C19	1.409 (3)	C14—H14C	0.9600
C11—C10—C3	119.1 (2)	C2—C1—C12	121.5 (2)
C11—C10—C9	134.5 (2)	C2—C1—H1	119.2
C3—C10—C9	106.39 (19)	C12—C1—H1	119.2
C12—C11—C10	119.8 (2)	C21—C22—C23	121.0 (2)
C12—C11—H11	120.1	C21—C22—H22	119.5
C10—C11—H11	120.1	C23—C22—H22	119.5
C15—N2—C12	119.2 (2)	C7—C8—C9	119.0 (2)
C20—O1—C25	117.2 (2)	C7—C8—H8	120.5
N3—C23—C18	122.6 (2)	C9—C8—H8	120.5
N3—C23—C22	119.6 (2)	C16—C17—C18	121.7 (2)
C18—C23—C22	117.8 (2)	C16—C17—H17	119.1
C24—N3—C23	117.3 (2)	C18—C17—H17	119.1
C4—N1—C3	108.95 (19)	N2—C15—C16	121.4 (2)
C4—N1—C13	125.7 (2)	N2—C15—H15	119.3
C3—N1—C13	125.4 (2)	C16—C15—H15	119.3
C8—C9—C4	119.6 (2)	C5—C6—C7	122.5 (3)
C8—C9—C10	133.8 (2)	C5—C6—H6	118.8
C4—C9—C10	106.5 (2)	C7—C6—H6	118.8
N1—C3—C2	129.5 (2)	N1—C13—C14	112.8 (2)
N1—C3—C10	109.1 (2)	N1—C13—H13A	109.0
C2—C3—C10	121.4 (2)	C14—C13—H13A	109.0
C11—C12—C1	119.7 (2)	N1—C13—H13B	109.0
C11—C12—N2	116.8 (2)	C14—C13—H13B	109.0
C1—C12—N2	123.5 (2)	H13A—C13—H13B	107.8
N1—C4—C5	129.5 (2)	C22—C21—C20	120.8 (2)
N1—C4—C9	109.0 (2)	C22—C21—H21	119.6
C5—C4—C9	121.4 (2)	C20—C21—H21	119.6
C1—C2—C3	118.3 (2)	C6—C5—C4	117.1 (2)
C1—C2—H2	120.8	C6—C5—H5	121.5
C3—C2—H2	120.8	C4—C5—H5	121.5
N3—C24—C16	126.5 (2)	C8—C7—C6	120.4 (3)
N3—C24—Cl1	115.38 (18)	C8—C7—H7	119.8
C16—C24—Cl1	118.17 (19)	C6—C7—H7	119.8
C17—C18—C23	116.6 (2)	O1—C25—H25A	109.5
C17—C18—C19	123.2 (2)	O1—C25—H25B	109.5
C23—C18—C19	120.2 (2)	H25A—C25—H25B	109.5
C20—C19—C18	119.9 (2)	O1—C25—H25C	109.5
C20—C19—H19	120.1	H25A—C25—H25C	109.5
C18—C19—H19	120.1	H25B—C25—H25C	109.5
C17—C16—C24	115.2 (2)	C13—C14—H14A	109.5
C17—C16—C15	121.8 (2)	C13—C14—H14B	109.5
C24—C16—C15	122.9 (2)	H14A—C14—H14B	109.5
C19—C20—O1	125.2 (2)	C13—C14—H14C	109.5
C19—C20—C21	120.2 (2)	H14A—C14—H14C	109.5
O1—C20—C21	114.6 (2)	H14B—C14—H14C	109.5
C3—C10—C11—C12	−2.3 (3)	C22—C23—C18—C19	2.0 (3)
C9—C10—C11—C12	176.1 (2)	C17—C18—C19—C20	176.0 (2)
C18—C23—N3—C24	−2.7 (3)	C23—C18—C19—C20	−1.4 (4)
C22—C23—N3—C24	177.2 (2)	N3—C24—C16—C17	3.5 (4)
C11—C10—C9—C8	−0.4 (4)	Cl1—C24—C16—C17	−176.18 (17)
C3—C10—C9—C8	178.2 (2)	N3—C24—C16—C15	−173.0 (2)
C11—C10—C9—C4	−178.9 (2)	Cl1—C24—C16—C15	7.3 (3)
C3—C10—C9—C4	−0.4 (2)	C18—C19—C20—O1	−178.3 (2)
C4—N1—C3—C2	180.0 (2)	C18—C19—C20—C21	−0.4 (4)
C13—N1—C3—C2	1.9 (4)	C25—O1—C20—C19	−5.4 (4)
C4—N1—C3—C10	0.0 (2)	C25—O1—C20—C21	176.6 (2)
C13—N1—C3—C10	−178.07 (19)	C3—C2—C1—C12	−0.7 (3)
C11—C10—C3—N1	179.03 (19)	C11—C12—C1—C2	−2.5 (3)
C9—C10—C3—N1	0.2 (2)	N2—C12—C1—C2	176.4 (2)
C11—C10—C3—C2	−1.0 (3)	N3—C23—C22—C21	179.4 (2)
C9—C10—C3—C2	−179.8 (2)	C18—C23—C22—C21	−0.7 (4)
C10—C11—C12—C1	4.0 (3)	C4—C9—C8—C7	1.3 (3)
C10—C11—C12—N2	−174.97 (19)	C10—C9—C8—C7	−177.1 (2)
C15—N2—C12—C11	150.7 (2)	C24—C16—C17—C18	−1.7 (3)
C15—N2—C12—C1	−28.2 (3)	C15—C16—C17—C18	174.9 (2)
C3—N1—C4—C5	−178.0 (2)	C23—C18—C17—C16	−1.9 (3)
C13—N1—C4—C5	0.0 (4)	C19—C18—C17—C16	−179.4 (2)
C3—N1—C4—C9	−0.2 (2)	C12—N2—C15—C16	−177.5 (2)
C13—N1—C4—C9	177.83 (19)	C17—C16—C15—N2	−16.1 (4)
C8—C9—C4—N1	−178.43 (19)	C24—C16—C15—N2	160.2 (2)
C10—C9—C4—N1	0.4 (2)	C4—N1—C13—C14	95.5 (3)
C8—C9—C4—C5	−0.4 (3)	C3—N1—C13—C14	−86.8 (3)
C10—C9—C4—C5	178.4 (2)	C23—C22—C21—C20	−1.1 (4)
N1—C3—C2—C1	−177.5 (2)	C19—C20—C21—C22	1.7 (4)
C10—C3—C2—C1	2.5 (3)	O1—C20—C21—C22	179.8 (2)
C23—N3—C24—C16	−1.4 (4)	C7—C6—C5—C4	1.2 (4)
C23—N3—C24—Cl1	178.33 (17)	N1—C4—C5—C6	176.7 (2)
N3—C23—C18—C17	4.2 (3)	C9—C4—C5—C6	−0.8 (3)
C22—C23—C18—C17	−175.7 (2)	C9—C8—C7—C6	−1.0 (4)
N3—C23—C18—C19	−178.1 (2)	C5—C6—C7—C8	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1i	0.93	2.87	3.718 (3)	152
C7—H7···Cg2ii	0.93	2.97	3.688 (2)	145