N,N-Diethyl-4-[1-phenyl-3-(pyridin-2-yl)-4,5-di-hydro-1H-pyrazol-5-yl]aniline.

In the title mol-ecule, C24H26N4, the pyrazoline ring assumes an envelope conformation with the aniline-bearing C atom at the flap position. The benzene ring and the pyridine ring form with the pyrazoline ring dihedral angles of 4.53 (1) and 6.26 (1)°, respectively. In turn, the aniline group is nearly perpendicular to the pyrazoline ring [dihedral angle = 79.96 (1)°]. The ethyl groups of the di-ethyl-amine substituent are disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8).

Related literature

For background to the design and synthesis of the title compound and for related structures, see: Chen et al. (2008 ▶); Dong et al. (2010 ▶); Guo et al. (2010 ▶); Liu et al. (2010 ▶).

Experimental

Crystal data

C24H26N4

M = 370.49

Monoclinic,

a = 14.902 (5) Å

b = 11.314 (5) Å

c = 12.479 (5) Å

β = 94.644 (5)°

V = 2097.1 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.979, T max = 0.986

14365 measured reflections

3678 independent reflections

2511 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.241

S = 1.06

3678 reflections

294 parameters

507 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019879/gk2584sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019879/gk2584Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019879/gk2584Isup3.cml

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

C24H26N4	F(000) = 792
Mr = 370.49	Dx = 1.173 Mg m−3
Monoclinic, P21/c	Melting point: 391 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 14.902 (5) Å	Cell parameters from 3174 reflections
b = 11.314 (5) Å	θ = 2.4–23.1°
c = 12.479 (5) Å	µ = 0.07 mm−1
β = 94.644 (5)°	T = 296 K
V = 2097.1 (14) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker SMART APEX CCD diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
Tmin = 0.979, Tmax = 0.986	k = −13→13
14365 measured reflections	l = −14→14

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1447P)2 + 0.5666P] where P = (Fo2 + 2Fc2)/3
3678 reflections	(Δ/σ)max = 0.002
294 parameters	Δρmax = 0.37 e Å−3
507 restraints	Δρmin = −0.52 e Å−3

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	Occ. (<1)
C1	0.3073 (2)	−0.2820 (3)	0.4677 (3)	0.0539 (7)
C2	0.3140 (2)	−0.3449 (3)	0.5624 (3)	0.0662 (9)
H2	0.3316	−0.3074	0.6271	0.079*
C3	0.2946 (3)	−0.4632 (3)	0.5606 (4)	0.0815 (10)
H3	0.3000	−0.5071	0.6239	0.098*
C4	0.2674 (3)	−0.5163 (4)	0.4651 (4)	0.0864 (11)
H4	0.2538	−0.5965	0.4616	0.104*
C5	0.2611 (3)	−0.4473 (4)	0.3752 (4)	0.0821 (11)
H5	0.2423	−0.4835	0.3103	0.099*
C6	0.32889 (19)	−0.1562 (3)	0.4637 (2)	0.0504 (7)
C7	0.3245 (2)	−0.0819 (3)	0.3641 (2)	0.0561 (8)
H7A	0.2659	−0.0876	0.3245	0.067*
H7B	0.3706	−0.1047	0.3175	0.067*
C8	0.3415 (2)	0.0433 (3)	0.4096 (2)	0.0519 (7)
H8	0.3888	0.0822	0.3723	0.062*
C9	0.40911 (18)	0.0948 (2)	0.5983 (2)	0.0485 (7)
C10	0.4309 (2)	0.2102 (3)	0.5699 (3)	0.0597 (8)
H10	0.4198	0.2357	0.4992	0.072*
C11	0.4691 (2)	0.2863 (3)	0.6473 (3)	0.0625 (8)
H11	0.4848	0.3623	0.6275	0.075*
C12	0.4846 (2)	0.2523 (3)	0.7527 (3)	0.0633 (8)
H12	0.5106	0.3043	0.8039	0.076*
C13	0.4608 (2)	0.1400 (3)	0.7814 (3)	0.0610 (8)
H13	0.4703	0.1164	0.8528	0.073*
C14	0.4230 (2)	0.0613 (3)	0.7055 (2)	0.0529 (7)
H14	0.4069	−0.0142	0.7264	0.064*
C15	0.2580 (2)	0.1196 (3)	0.4035 (2)	0.0504 (7)
C16	0.2344 (2)	0.1879 (3)	0.3139 (3)	0.0572 (8)
H16	0.2736	0.1927	0.2597	0.069*
C17	0.1544 (2)	0.2488 (3)	0.3028 (3)	0.0670 (9)
H17	0.1410	0.2942	0.2415	0.080*
C18	0.0926 (3)	0.2446 (3)	0.3813 (3)	0.0760 (9)
C19	0.1985 (2)	0.1174 (3)	0.4831 (3)	0.0656 (9)
H19	0.2132	0.0738	0.5452	0.079*
C20	0.1182 (3)	0.1780 (4)	0.4727 (3)	0.0767 (10)
H20	0.0801	0.1744	0.5280	0.092*
C21	−0.0287 (6)	0.3410 (9)	0.2615 (7)	0.1169 (19)	0.624 (8)
H21A	0.0049	0.3045	0.2069	0.140*	0.624 (8)
H21B	−0.0903	0.3128	0.2514	0.140*	0.624 (8)
C22	−0.0282 (8)	0.4663 (10)	0.2471 (10)	0.151 (3)	0.624 (8)
H22A	−0.0691	0.5022	0.2931	0.227*	0.624 (8)
H22B	−0.0465	0.4849	0.1735	0.227*	0.624 (8)
H22C	0.0315	0.4961	0.2651	0.227*	0.624 (8)
C23	−0.0521 (6)	0.2931 (9)	0.4622 (8)	0.1072 (18)	0.624 (8)
H23A	−0.0175	0.3015	0.5310	0.129*	0.624 (8)
H23B	−0.0961	0.3564	0.4556	0.129*	0.624 (8)
C24	−0.1004 (7)	0.1750 (9)	0.4583 (10)	0.127 (2)	0.624 (8)
H24A	−0.1462	0.1748	0.3995	0.190*	0.624 (8)
H24B	−0.1277	0.1627	0.5245	0.190*	0.624 (8)
H24C	−0.0580	0.1129	0.4483	0.190*	0.624 (8)
C21'	−0.0141 (8)	0.4066 (13)	0.2996 (14)	0.118 (2)	0.376 (8)
H21C	0.0205	0.3986	0.2373	0.142*	0.376 (8)
H21D	−0.0766	0.3947	0.2739	0.142*	0.376 (8)
C22'	−0.0068 (15)	0.5244 (13)	0.3306 (17)	0.146 (3)	0.376 (8)
H22D	−0.0077	0.5736	0.2679	0.219*	0.376 (8)
H22E	0.0488	0.5360	0.3739	0.219*	0.376 (8)
H22F	−0.0563	0.5449	0.3715	0.219*	0.376 (8)
C23'	−0.0689 (11)	0.2690 (15)	0.4247 (14)	0.108 (2)	0.376 (8)
H23C	−0.1125	0.3326	0.4158	0.129*	0.376 (8)
H23D	−0.0518	0.2612	0.5010	0.129*	0.376 (8)
C24'	−0.1138 (11)	0.1567 (14)	0.3859 (17)	0.128 (3)	0.376 (8)
H24D	−0.1529	0.1725	0.3226	0.191*	0.376 (8)
H24E	−0.1483	0.1253	0.4410	0.191*	0.376 (8)
H24F	−0.0689	0.1002	0.3692	0.191*	0.376 (8)
N1	0.0113 (3)	0.3032 (4)	0.3708 (4)	0.1077 (11)
N2	0.37522 (17)	0.0154 (2)	0.5210 (2)	0.0555 (7)
N3	0.35871 (16)	−0.0994 (2)	0.5487 (2)	0.0502 (7)
N4	0.2797 (2)	−0.3311 (3)	0.3729 (2)	0.0696 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (15)	0.0507 (15)	0.0640 (17)	0.0005 (12)	0.0025 (13)	−0.0102 (13)
C2	0.0719 (19)	0.0515 (16)	0.0733 (18)	−0.0062 (14)	−0.0061 (15)	−0.0017 (14)
C3	0.093 (2)	0.0560 (18)	0.093 (2)	−0.0094 (17)	−0.0055 (19)	0.0011 (16)
C4	0.091 (2)	0.060 (2)	0.107 (2)	−0.0093 (18)	0.000 (2)	−0.0174 (17)
C5	0.085 (2)	0.070 (2)	0.091 (2)	−0.0079 (19)	0.0039 (19)	−0.0321 (18)
C6	0.0451 (14)	0.0499 (15)	0.0558 (16)	0.0017 (12)	0.0025 (12)	−0.0043 (12)
C7	0.0558 (16)	0.0582 (16)	0.0542 (16)	0.0055 (13)	0.0029 (13)	−0.0026 (13)
C8	0.0491 (15)	0.0538 (16)	0.0528 (16)	−0.0022 (12)	0.0035 (12)	0.0057 (13)
C9	0.0431 (14)	0.0415 (14)	0.0601 (15)	0.0028 (11)	−0.0010 (12)	−0.0026 (12)
C10	0.0593 (17)	0.0488 (16)	0.0701 (17)	−0.0025 (13)	0.0002 (14)	0.0051 (13)
C11	0.0580 (17)	0.0444 (15)	0.0845 (19)	−0.0060 (13)	0.0023 (15)	−0.0043 (14)
C12	0.0580 (17)	0.0526 (16)	0.0785 (18)	0.0024 (13)	0.0012 (15)	−0.0182 (15)
C13	0.0638 (17)	0.0558 (16)	0.0628 (17)	0.0054 (14)	0.0012 (14)	−0.0082 (14)
C14	0.0549 (15)	0.0440 (15)	0.0595 (16)	0.0041 (12)	0.0027 (13)	−0.0022 (12)
C15	0.0514 (14)	0.0491 (15)	0.0505 (14)	−0.0032 (12)	0.0020 (11)	0.0032 (12)
C16	0.0616 (16)	0.0541 (16)	0.0554 (16)	−0.0025 (13)	0.0011 (13)	0.0052 (13)
C17	0.0693 (18)	0.0611 (18)	0.0687 (18)	0.0042 (15)	−0.0066 (14)	0.0106 (15)
C18	0.0663 (17)	0.0719 (19)	0.089 (2)	0.0109 (15)	0.0018 (15)	0.0032 (17)
C19	0.0621 (17)	0.0722 (19)	0.0636 (17)	0.0075 (15)	0.0114 (14)	0.0130 (15)
C20	0.0684 (19)	0.085 (2)	0.0787 (19)	0.0111 (16)	0.0192 (16)	0.0080 (17)
C21	0.106 (3)	0.121 (3)	0.123 (3)	0.024 (3)	0.004 (2)	0.006 (3)
C22	0.164 (4)	0.140 (4)	0.150 (4)	0.008 (3)	0.005 (3)	0.021 (3)
C23	0.090 (3)	0.113 (3)	0.119 (3)	0.024 (2)	0.009 (2)	−0.002 (3)
C24	0.114 (4)	0.133 (4)	0.134 (4)	0.001 (3)	0.012 (3)	0.001 (3)
C21'	0.112 (3)	0.119 (3)	0.123 (3)	0.022 (3)	0.003 (3)	0.013 (3)
C22'	0.153 (5)	0.135 (4)	0.149 (5)	0.003 (4)	0.008 (4)	0.005 (3)
C23'	0.094 (3)	0.114 (3)	0.116 (3)	0.019 (3)	0.013 (3)	−0.001 (3)
C24'	0.123 (4)	0.130 (4)	0.130 (5)	0.000 (3)	0.013 (4)	−0.002 (4)
N1	0.0858 (18)	0.116 (2)	0.121 (2)	0.0296 (16)	0.0086 (16)	0.0113 (17)
N2	0.0629 (16)	0.0440 (14)	0.0571 (15)	−0.0043 (11)	−0.0099 (12)	0.0060 (11)
N3	0.0510 (14)	0.0407 (14)	0.0578 (15)	−0.0016 (11)	−0.0027 (11)	0.0016 (11)
N4	0.0717 (19)	0.0666 (19)	0.0706 (19)	−0.0078 (14)	0.0057 (14)	−0.0201 (15)

C1—N4	1.341 (4)	C17—H17	0.9300
C1—C2	1.377 (5)	C18—N1	1.378 (5)
C1—C6	1.461 (4)	C18—C20	1.394 (5)
C2—C3	1.370 (5)	C19—C20	1.377 (5)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.366 (6)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.429 (12)
C4—C5	1.365 (6)	C21—N1	1.506 (9)
C4—H4	0.9300	C21—H21A	0.9700
C5—N4	1.345 (5)	C21—H21B	0.9700
C5—H5	0.9300	C22—H22A	0.9600
C6—N3	1.288 (4)	C22—H22B	0.9600
C6—C7	1.498 (4)	C22—H22C	0.9600
C7—C8	1.540 (4)	C23—C24	1.516 (12)
C7—H7A	0.9700	C23—N1	1.543 (10)
C7—H7B	0.9700	C23—H23A	0.9700
C8—N2	1.473 (4)	C23—H23B	0.9700
C8—C15	1.511 (4)	C24—H24A	0.9600
C8—H8	0.9800	C24—H24B	0.9600
C9—N2	1.383 (4)	C24—H24C	0.9600
C9—C14	1.390 (4)	C21'—C22'	1.390 (16)
C9—C10	1.398 (4)	C21'—N1	1.499 (12)
C10—C11	1.382 (5)	C21'—H21C	0.9700
C10—H10	0.9300	C21'—H21D	0.9700
C11—C12	1.372 (5)	C22'—H22D	0.9600
C11—H11	0.9300	C22'—H22E	0.9600
C12—C13	1.374 (5)	C22'—H22F	0.9600
C12—H12	0.9300	C23'—N1	1.470 (14)
C13—C14	1.386 (4)	C23'—C24'	1.498 (17)
C13—H13	0.9300	C23'—H23C	0.9700
C14—H14	0.9300	C23'—H23D	0.9700
C15—C16	1.381 (4)	C24'—H24D	0.9600
C15—C19	1.383 (4)	C24'—H24E	0.9600
C16—C17	1.375 (5)	C24'—H24F	0.9600
C16—H16	0.9300	N2—N3	1.371 (3)
C17—C18	1.398 (5)
N4—C1—C2	122.6 (3)	N1—C18—C17	122.8 (4)
N4—C1—C6	115.2 (3)	C20—C18—C17	116.1 (3)
C2—C1—C6	122.1 (3)	C20—C19—C15	121.7 (3)
C3—C2—C1	119.4 (3)	C20—C19—H19	119.1
C3—C2—H2	120.3	C15—C19—H19	119.1
C1—C2—H2	120.3	C19—C20—C18	121.7 (3)
C4—C3—C2	119.4 (4)	C19—C20—H20	119.2
C4—C3—H3	120.3	C18—C20—H20	119.2
C2—C3—H3	120.3	C22—C21—N1	112.9 (8)
C5—C4—C3	117.5 (4)	C22—C21—H21A	109.0
C5—C4—H4	121.2	N1—C21—H21A	109.0
C3—C4—H4	121.2	C22—C21—H21B	109.0
N4—C5—C4	125.2 (4)	N1—C21—H21B	109.0
N4—C5—H5	117.4	H21A—C21—H21B	107.8
C4—C5—H5	117.4	C24—C23—N1	111.0 (7)
N3—C6—C1	121.4 (3)	C24—C23—H23A	109.4
N3—C6—C7	113.1 (3)	N1—C23—H23A	109.4
C1—C6—C7	125.4 (3)	C24—C23—H23B	109.4
C6—C7—C8	102.4 (2)	N1—C23—H23B	109.4
C6—C7—H7A	111.3	H23A—C23—H23B	108.0
C8—C7—H7A	111.3	C22'—C21'—N1	124.9 (14)
C6—C7—H7B	111.3	C22'—C21'—H21C	106.1
C8—C7—H7B	111.3	N1—C21'—H21C	106.1
H7A—C7—H7B	109.2	C22'—C21'—H21D	106.1
N2—C8—C15	112.8 (2)	N1—C21'—H21D	106.1
N2—C8—C7	100.6 (2)	H21C—C21'—H21D	106.3
C15—C8—C7	113.4 (2)	C21'—C22'—H22D	109.5
N2—C8—H8	109.9	C21'—C22'—H22E	109.5
C15—C8—H8	109.9	H22D—C22'—H22E	109.5
C7—C8—H8	109.9	C21'—C22'—H22F	109.5
N2—C9—C14	120.8 (3)	H22D—C22'—H22F	109.5
N2—C9—C10	120.6 (3)	H22E—C22'—H22F	109.5
C14—C9—C10	118.6 (3)	N1—C23'—C24'	115.7 (12)
C11—C10—C9	119.7 (3)	N1—C23'—H23C	108.4
C11—C10—H10	120.1	C24'—C23'—H23C	108.4
C9—C10—H10	120.1	N1—C23'—H23D	108.4
C12—C11—C10	121.5 (3)	C24'—C23'—H23D	108.4
C12—C11—H11	119.2	H23C—C23'—H23D	107.4
C10—C11—H11	119.2	C23'—C24'—H24D	109.5
C11—C12—C13	118.8 (3)	C23'—C24'—H24E	109.5
C11—C12—H12	120.6	H24D—C24'—H24E	109.5
C13—C12—H12	120.6	C23'—C24'—H24F	109.5
C12—C13—C14	121.0 (3)	H24D—C24'—H24F	109.5
C12—C13—H13	119.5	H24E—C24'—H24F	109.5
C14—C13—H13	119.5	C18—N1—C23'	124.9 (8)
C13—C14—C9	120.2 (3)	C18—N1—C21'	127.5 (6)
C13—C14—H14	119.9	C23'—N1—C21'	107.5 (9)
C9—C14—H14	119.9	C18—N1—C21	120.2 (5)
C16—C15—C19	117.1 (3)	C23'—N1—C21	102.2 (8)
C16—C15—C8	121.0 (3)	C18—N1—C23	118.7 (5)
C19—C15—C8	121.7 (3)	C21'—N1—C23	110.8 (7)
C17—C16—C15	121.6 (3)	C21—N1—C23	118.0 (6)
C17—C16—H16	119.2	N3—N2—C9	120.2 (2)
C15—C16—H16	119.2	N3—N2—C8	112.7 (2)
C16—C17—C18	121.8 (3)	C9—N2—C8	126.6 (2)
C16—C17—H17	119.1	C6—N3—N2	108.8 (2)
C18—C17—H17	119.1	C1—N4—C5	115.8 (3)
N1—C18—C20	121.2 (4)
N4—C1—C2—C3	2.0 (5)	C20—C18—N1—C21'	158.4 (10)
C6—C1—C2—C3	−178.6 (3)	C17—C18—N1—C21'	−21.0 (11)
C1—C2—C3—C4	−1.1 (6)	C20—C18—N1—C21	−160.3 (6)
C2—C3—C4—C5	0.1 (6)	C17—C18—N1—C21	20.3 (8)
C3—C4—C5—N4	0.2 (7)	C20—C18—N1—C23	−0.5 (7)
N4—C1—C6—N3	−177.9 (3)	C17—C18—N1—C23	−179.9 (5)
C2—C1—C6—N3	2.7 (5)	C24'—C23'—N1—C18	−69.5 (17)
N4—C1—C6—C7	−1.5 (4)	C24'—C23'—N1—C21'	107.3 (16)
C2—C1—C6—C7	179.1 (3)	C24'—C23'—N1—C21	71.6 (16)
N3—C6—C7—C8	−10.6 (3)	C24'—C23'—N1—C23	−150 (4)
C1—C6—C7—C8	172.7 (3)	C22'—C21'—N1—C18	−93.3 (15)
C6—C7—C8—N2	14.0 (3)	C22'—C21'—N1—C23'	90.1 (16)
C6—C7—C8—C15	−106.7 (3)	C22'—C21'—N1—C21	176 (2)
N2—C9—C10—C11	−176.6 (3)	C22'—C21'—N1—C23	67.0 (16)
C14—C9—C10—C11	2.8 (5)	C22—C21—N1—C18	−110.5 (8)
C9—C10—C11—C12	−1.5 (5)	C22—C21—N1—C23'	106.1 (10)
C10—C11—C12—C13	−0.3 (5)	C22—C21—N1—C21'	2.9 (10)
C11—C12—C13—C14	0.8 (5)	C22—C21—N1—C23	89.6 (9)
C12—C13—C14—C9	0.5 (5)	C24—C23—N1—C18	−77.2 (8)
N2—C9—C14—C13	177.0 (3)	C24—C23—N1—C23'	35 (2)
C10—C9—C14—C13	−2.4 (4)	C24—C23—N1—C21'	120.6 (10)
N2—C8—C15—C16	157.4 (3)	C24—C23—N1—C21	83.1 (9)
C7—C8—C15—C16	−89.1 (3)	C14—C9—N2—N3	−3.0 (4)
N2—C8—C15—C19	−27.6 (4)	C10—C9—N2—N3	176.4 (3)
C7—C8—C15—C19	85.9 (4)	C14—C9—N2—C8	167.8 (3)
C19—C15—C16—C17	−1.5 (5)	C10—C9—N2—C8	−12.8 (5)
C8—C15—C16—C17	173.7 (3)	C15—C8—N2—N3	106.4 (3)
C15—C16—C17—C18	−0.3 (5)	C7—C8—N2—N3	−14.7 (3)
C16—C17—C18—N1	−178.7 (4)	C15—C8—N2—C9	−65.0 (4)
C16—C17—C18—C20	1.9 (6)	C7—C8—N2—C9	173.9 (3)
C16—C15—C19—C20	1.6 (5)	C1—C6—N3—N2	178.5 (3)
C8—C15—C19—C20	−173.6 (3)	C7—C6—N3—N2	1.7 (3)
C15—C19—C20—C18	0.1 (6)	C9—N2—N3—C6	−179.1 (3)
N1—C18—C20—C19	178.8 (4)	C8—N2—N3—C6	8.9 (3)
C17—C18—C20—C19	−1.8 (6)	C2—C1—N4—C5	−1.7 (5)
C20—C18—N1—C23'	−25.5 (10)	C6—C1—N4—C5	178.9 (3)
C17—C18—N1—C23'	155.1 (9)	C4—C5—N4—C1	0.6 (6)