Ethyl 2,6-bis-(4-chloro-phen-yl)-4-(4-methyl-anilino)-1-(4-methyl-phen-yl)-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title mol-ecule, C34H32Cl2N2O2, the tetra-hydro-pyridine ring adopts a distorted boat conformation and both 4-chloro-phenyl substituents are in axial positions. An intra-molecular N-H⋯O hydrogen bond is formed by the amino group and carbonyl O atom. In the crystal, weak C-H⋯Cl inter-actions link the mol-ecules into chains along [010].

Related literature

For general background to functionalized piperidines, see: Pinder (1992 ▶); Watson et al. (2000 ▶); Breman et al. (2001 ▶); Kamei et al. (2005 ▶). For related structures, see: Sambyal et al. (2011 ▶); Brahmachari & Das (2012 ▶); Khan et al. (2010 ▶); Anthal et al. (2013 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C34H32Cl2N2O2

M = 571.52

Triclinic,

a = 10.0851 (6) Å

b = 12.4340 (8) Å

c = 14.2414 (10) Å

α = 113.405 (6)°

β = 102.233 (5)°

γ = 101.194 (5)°

V = 1522.63 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.853, T max = 1.000

13336 measured reflections

5342 independent reflections

2181 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.109

S = 0.89

5342 reflections

365 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005126/gk2555sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005126/gk2555Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005126/gk2555Isup3.cml

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

C34H32Cl2N2O2	Z = 2
Mr = 571.52	F(000) = 600
Triclinic, P1	Dx = 1.247 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0851 (6) Å	Cell parameters from 3234 reflections
b = 12.4340 (8) Å	θ = 3.3–28.9°
c = 14.2414 (10) Å	µ = 0.25 mm−1
α = 113.405 (6)°	T = 293 K
β = 102.233 (5)°	Block-shaped, white
γ = 101.194 (5)°	0.30 × 0.20 × 0.20 mm
V = 1522.63 (17) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5342 independent reflections
Radiation source: fine-focus sealed tube	2181 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.853, Tmax = 1.000	l = −16→16
13336 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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0203P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
5342 reflections	Δρmax = 0.25 e Å−3
365 parameters	Δρmin = −0.21 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: 0.0060 (5)

Experimental. 1H-NMR (400 MHz, CDCl3): δH 1.46 (t, J = 6.8 Hz, 3H), 2.16 (s, 3H), 2.27 (s, 3H), 2.70 (dd, J = 2.4, 15.2 Hz, 1H), 2.77 (dd, J = 5.2, 15.2 Hz, 1H), 4.29–4.33 (m, 1H), 4.35–4.44 (m, 1H), 5.05 (br s, 1H), 6.29 (t, J = 8, 11.2 Hz, 3H), 6.36 (d, J = 8.8 Hz, 2H), 6.88 (d, J = 8.4 Hz, 2H), 6.94 (d, J = 8 Hz, 2H), 7.05(d, J = 8.4 Hz, 2H), 7.21–7.26 (m, 6H), 10.20 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δC 14.82, 20.13, 20.92, 33.62, 54.84, 57.35, 59.74, 97.24, 113.0, 125.77, 125.83, 127.85, 128.07, 128.35, 128.73, 129.59, 132.01, 132.76, 135.01, 135.88, 141.23, 142.80, 144.37, 156.16, 168.03. IR νmax (KBr): 3242, 3024, 2974, 2915, 2870, 1653, 1589, 1514, 1483, 1256, 1172, 1076, 1012, 804, 678 cm-1.CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.22422 (13)	1.01537 (10)	0.47443 (10)	0.1168 (5)
Cl2	0.36062 (12)	−0.11737 (10)	0.09237 (10)	0.1157 (5)
O1	0.0417 (3)	0.3327 (2)	−0.03361 (19)	0.0828 (8)
O2	0.2464 (2)	0.4814 (2)	0.01502 (18)	0.0734 (7)
N1	0.4134 (2)	0.4914 (2)	0.29596 (19)	0.0496 (7)
N2	−0.0058 (3)	0.2735 (2)	0.1225 (2)	0.0689 (9)
H2	−0.0501	0.2706	0.0625	0.083*
C2	0.3304 (3)	0.5348 (3)	0.2295 (2)	0.0493 (8)
H2A	0.3889	0.5539	0.1880	0.059*
C3	0.1954 (3)	0.4340 (3)	0.1478 (3)	0.0488 (8)
C4	0.1191 (3)	0.3651 (3)	0.1837 (3)	0.0532 (9)
C5	0.1815 (3)	0.3929 (3)	0.2988 (2)	0.0564 (9)
H5A	0.1303	0.3288	0.3122	0.068*
H5B	0.1728	0.4708	0.3463	0.068*
C6	0.3382 (3)	0.3997 (3)	0.3215 (3)	0.0510 (9)
H6	0.3792	0.4284	0.3993	0.061*
C7	0.1516 (4)	0.4089 (3)	0.0359 (3)	0.0586 (10)
C8	0.2095 (4)	0.4698 (4)	−0.0935 (3)	0.0985 (14)
H8A	0.2042	0.3881	−0.1448	0.118*
H8B	0.1170	0.4815	−0.1128	0.118*
C9	0.3167 (5)	0.5614 (3)	−0.0972 (3)	0.1185 (16)
H9A	0.3235	0.6418	−0.0446	0.178*
H9B	0.2912	0.5567	−0.1679	0.178*
H9C	0.4070	0.5469	−0.0815	0.178*
C10	0.3019 (3)	0.6540 (3)	0.2953 (3)	0.0507 (9)
C11	0.2103 (3)	0.6973 (3)	0.2428 (3)	0.0648 (10)
H11	0.1642	0.6512	0.1688	0.078*
C12	0.1861 (4)	0.8064 (4)	0.2976 (3)	0.0746 (11)
H12	0.1236	0.8330	0.2605	0.090*
C13	0.2527 (4)	0.8763 (3)	0.4059 (3)	0.0688 (11)
C14	0.3449 (4)	0.8373 (3)	0.4613 (3)	0.0729 (11)
H14	0.3911	0.8849	0.5352	0.087*
C15	0.3683 (3)	0.7264 (3)	0.4058 (3)	0.0608 (10)
H15	0.4300	0.6998	0.4435	0.073*
C16	0.5610 (3)	0.5394 (3)	0.3382 (2)	0.0447 (8)
C17	0.6367 (3)	0.6453 (3)	0.3357 (2)	0.0524 (9)
H17	0.5870	0.6842	0.3038	0.063*
C18	0.7817 (3)	0.6921 (3)	0.3795 (3)	0.0573 (9)
H18	0.8281	0.7620	0.3758	0.069*
C19	0.8621 (3)	0.6397 (3)	0.4289 (3)	0.0580 (9)
C20	0.7892 (3)	0.5358 (3)	0.4315 (3)	0.0606 (10)
H20	0.8403	0.4981	0.4641	0.073*
C21	0.6432 (3)	0.4858 (3)	0.3877 (2)	0.0528 (9)
H21	0.5981	0.4152	0.3909	0.063*
C22	0.3522 (3)	0.2723 (3)	0.2641 (3)	0.0495 (9)
C23	0.3729 (3)	0.2285 (3)	0.1648 (3)	0.0624 (10)
H23	0.3852	0.2806	0.1331	0.075*
C24	0.3758 (3)	0.1092 (3)	0.1110 (3)	0.0707 (11)
H24	0.3888	0.0809	0.0437	0.085*
C25	0.3591 (4)	0.0333 (3)	0.1587 (4)	0.0746 (12)
C26	0.3418 (3)	0.0744 (4)	0.2592 (3)	0.0734 (12)
H26	0.3337	0.0229	0.2918	0.088*
C27	0.3366 (3)	0.1935 (3)	0.3110 (3)	0.0645 (10)
H27	0.3225	0.2211	0.3780	0.077*
C28	−0.0709 (3)	0.1806 (3)	0.1490 (3)	0.0627 (10)
C29	−0.1797 (4)	0.1888 (3)	0.1914 (3)	0.0768 (12)
H29	−0.2129	0.2565	0.2048	0.092*
C30	−0.2411 (4)	0.0965 (4)	0.2146 (3)	0.0907 (14)
H30	−0.3161	0.1024	0.2427	0.109*
C31	−0.1929 (5)	−0.0037 (4)	0.1966 (4)	0.0874 (14)
C32	−0.0836 (4)	−0.0106 (4)	0.1543 (3)	0.0900 (14)
H32	−0.0503	−0.0782	0.1407	0.108*
C33	−0.0212 (4)	0.0819 (4)	0.1314 (3)	0.0789 (12)
H33	0.0545	0.0767	0.1040	0.095*
C34	1.0228 (3)	0.6960 (3)	0.4809 (3)	0.0972 (14)
H34A	1.0533	0.6767	0.5393	0.146*
H34B	1.0482	0.7839	0.5082	0.146*
H34C	1.0686	0.6630	0.4282	0.146*
C35	−0.2600 (4)	−0.1064 (4)	0.2214 (4)	0.145 (2)
H35A	−0.3102	−0.1804	0.1551	0.217*
H35B	−0.3255	−0.0821	0.2596	0.217*
H35C	−0.1865	−0.1212	0.2653	0.217*

	U11	U22	U33	U12	U13	U23
Cl1	0.1645 (12)	0.0713 (8)	0.1186 (11)	0.0572 (8)	0.0661 (9)	0.0273 (8)
Cl2	0.1328 (10)	0.0596 (8)	0.1190 (11)	0.0344 (7)	0.0103 (8)	0.0197 (7)
O1	0.0872 (19)	0.0779 (19)	0.0520 (17)	−0.0019 (15)	−0.0075 (14)	0.0274 (16)
O2	0.0933 (18)	0.0777 (18)	0.0403 (15)	0.0102 (14)	0.0167 (13)	0.0285 (14)
N1	0.0462 (16)	0.0515 (18)	0.0501 (18)	0.0096 (13)	0.0088 (13)	0.0281 (16)
N2	0.0542 (18)	0.072 (2)	0.065 (2)	0.0005 (16)	−0.0024 (15)	0.0360 (19)
C2	0.052 (2)	0.052 (2)	0.039 (2)	0.0114 (17)	0.0099 (16)	0.0212 (19)
C3	0.055 (2)	0.047 (2)	0.039 (2)	0.0123 (17)	0.0119 (17)	0.0171 (18)
C4	0.046 (2)	0.056 (2)	0.049 (2)	0.0140 (18)	0.0053 (18)	0.021 (2)
C5	0.055 (2)	0.058 (2)	0.050 (2)	0.0096 (17)	0.0156 (18)	0.022 (2)
C6	0.054 (2)	0.053 (2)	0.039 (2)	0.0085 (17)	0.0109 (16)	0.0204 (19)
C7	0.072 (3)	0.052 (2)	0.046 (2)	0.016 (2)	0.013 (2)	0.020 (2)
C8	0.129 (4)	0.103 (4)	0.050 (3)	0.007 (3)	0.026 (2)	0.037 (3)
C9	0.209 (5)	0.080 (3)	0.077 (3)	0.037 (3)	0.069 (3)	0.038 (3)
C10	0.055 (2)	0.047 (2)	0.047 (2)	0.0133 (17)	0.0141 (17)	0.022 (2)
C11	0.078 (3)	0.052 (2)	0.052 (3)	0.0124 (19)	0.0099 (19)	0.021 (2)
C12	0.093 (3)	0.059 (3)	0.076 (3)	0.029 (2)	0.025 (3)	0.034 (3)
C13	0.080 (3)	0.049 (3)	0.072 (3)	0.020 (2)	0.030 (2)	0.019 (2)
C14	0.069 (3)	0.074 (3)	0.053 (3)	0.018 (2)	0.020 (2)	0.009 (2)
C15	0.057 (2)	0.071 (3)	0.046 (2)	0.0229 (19)	0.0156 (18)	0.017 (2)
C16	0.052 (2)	0.047 (2)	0.034 (2)	0.0149 (17)	0.0142 (16)	0.0169 (18)
C17	0.057 (2)	0.047 (2)	0.053 (2)	0.0179 (17)	0.0193 (18)	0.0213 (19)
C18	0.057 (2)	0.052 (2)	0.069 (3)	0.0158 (18)	0.0256 (19)	0.030 (2)
C19	0.046 (2)	0.062 (3)	0.062 (3)	0.0144 (18)	0.0170 (18)	0.025 (2)
C20	0.059 (2)	0.069 (3)	0.056 (2)	0.0197 (19)	0.0160 (19)	0.031 (2)
C21	0.059 (2)	0.050 (2)	0.049 (2)	0.0118 (17)	0.0175 (17)	0.0234 (19)
C22	0.052 (2)	0.047 (2)	0.047 (2)	0.0128 (16)	0.0126 (17)	0.022 (2)
C23	0.073 (2)	0.059 (3)	0.054 (3)	0.022 (2)	0.0195 (19)	0.024 (2)
C24	0.085 (3)	0.067 (3)	0.054 (3)	0.031 (2)	0.022 (2)	0.019 (2)
C25	0.080 (3)	0.047 (3)	0.076 (3)	0.017 (2)	0.003 (2)	0.021 (3)
C26	0.077 (3)	0.058 (3)	0.076 (3)	0.008 (2)	0.003 (2)	0.038 (3)
C27	0.071 (2)	0.060 (3)	0.060 (3)	0.011 (2)	0.0174 (19)	0.032 (2)
C28	0.050 (2)	0.065 (3)	0.061 (3)	0.005 (2)	0.0048 (19)	0.030 (2)
C29	0.072 (3)	0.076 (3)	0.088 (3)	0.023 (2)	0.028 (2)	0.041 (3)
C30	0.079 (3)	0.109 (4)	0.095 (4)	0.020 (3)	0.034 (2)	0.057 (3)
C31	0.075 (3)	0.094 (4)	0.086 (4)	0.003 (3)	0.006 (3)	0.055 (3)
C32	0.092 (3)	0.068 (3)	0.099 (4)	0.018 (3)	0.010 (3)	0.042 (3)
C33	0.065 (3)	0.082 (3)	0.088 (3)	0.020 (2)	0.021 (2)	0.040 (3)
C34	0.058 (3)	0.107 (4)	0.132 (4)	0.021 (2)	0.023 (2)	0.066 (3)
C35	0.143 (4)	0.142 (5)	0.169 (5)	0.002 (3)	0.030 (4)	0.118 (4)

Cl1—C13	1.731 (4)	C16—C21	1.403 (3)
Cl2—C25	1.737 (4)	C16—C17	1.405 (3)
O1—C7	1.220 (3)	C17—C18	1.364 (3)
O2—C7	1.347 (3)	C17—H17	0.9300
O2—C8	1.452 (3)	C18—C19	1.381 (4)
N1—C16	1.388 (3)	C18—H18	0.9300
N1—C6	1.455 (3)	C19—C20	1.376 (4)
N1—C2	1.460 (3)	C19—C34	1.518 (4)
N2—C4	1.354 (3)	C20—C21	1.375 (4)
N2—C28	1.437 (4)	C20—H20	0.9300
N2—H2	0.8600	C21—H21	0.9300
C2—C3	1.512 (4)	C22—C23	1.378 (4)
C2—C10	1.528 (4)	C22—C27	1.391 (4)
C2—H2A	0.9800	C23—C24	1.383 (4)
C3—C4	1.359 (4)	C23—H23	0.9300
C3—C7	1.443 (4)	C24—C25	1.369 (4)
C4—C5	1.494 (4)	C24—H24	0.9300
C5—C6	1.522 (3)	C25—C26	1.378 (5)
C5—H5A	0.9700	C26—C27	1.384 (4)
C5—H5B	0.9700	C26—H26	0.9300
C6—C22	1.519 (4)	C27—H27	0.9300
C6—H6	0.9800	C28—C29	1.362 (4)
C8—C9	1.436 (4)	C28—C33	1.367 (4)
C8—H8A	0.9700	C29—C30	1.387 (4)
C8—H8B	0.9700	C29—H29	0.9300
C9—H9A	0.9600	C30—C31	1.374 (5)
C9—H9B	0.9600	C30—H30	0.9300
C9—H9C	0.9600	C31—C32	1.365 (5)
C10—C11	1.386 (4)	C31—C35	1.529 (4)
C10—C15	1.389 (4)	C32—C33	1.389 (4)
C11—C12	1.370 (4)	C32—H32	0.9300
C11—H11	0.9300	C33—H33	0.9300
C12—C13	1.361 (4)	C34—H34A	0.9600
C12—H12	0.9300	C34—H34B	0.9600
C13—C14	1.374 (4)	C34—H34C	0.9600
C14—C15	1.386 (4)	C35—H35A	0.9600
C14—H14	0.9300	C35—H35B	0.9600
C15—H15	0.9300	C35—H35C	0.9600
C7—O2—C8	117.1 (3)	N1—C16—C17	122.3 (3)
C16—N1—C6	119.9 (2)	C21—C16—C17	116.1 (3)
C16—N1—C2	121.2 (2)	C18—C17—C16	121.2 (3)
C6—N1—C2	118.8 (2)	C18—C17—H17	119.4
C4—N2—C28	125.8 (3)	C16—C17—H17	119.4
C4—N2—H2	117.1	C17—C18—C19	122.5 (3)
C28—N2—H2	117.1	C17—C18—H18	118.8
N1—C2—C3	111.4 (2)	C19—C18—H18	118.8
N1—C2—C10	113.5 (2)	C20—C19—C18	116.8 (3)
C3—C2—C10	112.5 (2)	C20—C19—C34	121.4 (3)
N1—C2—H2A	106.3	C18—C19—C34	121.7 (3)
C3—C2—H2A	106.3	C21—C20—C19	122.2 (3)
C10—C2—H2A	106.3	C21—C20—H20	118.9
C4—C3—C7	121.3 (3)	C19—C20—H20	118.9
C4—C3—C2	116.8 (3)	C20—C21—C16	121.2 (3)
C7—C3—C2	121.9 (3)	C20—C21—H21	119.4
N2—C4—C3	124.8 (3)	C16—C21—H21	119.4
N2—C4—C5	118.9 (3)	C23—C22—C27	118.2 (3)
C3—C4—C5	116.4 (3)	C23—C22—C6	123.0 (3)
C4—C5—C6	109.2 (3)	C27—C22—C6	118.8 (3)
C4—C5—H5A	109.8	C22—C23—C24	121.7 (3)
C6—C5—H5A	109.8	C22—C23—H23	119.1
C4—C5—H5B	109.8	C24—C23—H23	119.1
C6—C5—H5B	109.8	C25—C24—C23	118.9 (4)
H5A—C5—H5B	108.3	C25—C24—H24	120.6
N1—C6—C22	114.5 (3)	C23—C24—H24	120.6
N1—C6—C5	109.8 (2)	C24—C25—C26	121.2 (4)
C22—C6—C5	110.3 (2)	C24—C25—Cl2	119.8 (4)
N1—C6—H6	107.3	C26—C25—Cl2	119.0 (3)
C22—C6—H6	107.3	C25—C26—C27	119.1 (3)
C5—C6—H6	107.3	C25—C26—H26	120.4
O1—C7—O2	122.2 (3)	C27—C26—H26	120.4
O1—C7—C3	125.6 (3)	C26—C27—C22	120.8 (4)
O2—C7—C3	112.2 (3)	C26—C27—H27	119.6
C9—C8—O2	108.8 (3)	C22—C27—H27	119.6
C9—C8—H8A	109.9	C29—C28—C33	119.5 (3)
O2—C8—H8A	109.9	C29—C28—N2	121.8 (3)
C9—C8—H8B	109.9	C33—C28—N2	118.7 (3)
O2—C8—H8B	109.9	C28—C29—C30	120.1 (4)
H8A—C8—H8B	108.3	C28—C29—H29	120.0
C8—C9—H9A	109.5	C30—C29—H29	120.0
C8—C9—H9B	109.5	C31—C30—C29	121.1 (4)
H9A—C9—H9B	109.5	C31—C30—H30	119.5
C8—C9—H9C	109.5	C29—C30—H30	119.5
H9A—C9—H9C	109.5	C32—C31—C30	118.2 (4)
H9B—C9—H9C	109.5	C32—C31—C35	120.2 (4)
C11—C10—C15	117.0 (3)	C30—C31—C35	121.6 (4)
C11—C10—C2	119.3 (3)	C31—C32—C33	121.0 (4)
C15—C10—C2	123.6 (3)	C31—C32—H32	119.5
C12—C11—C10	121.5 (3)	C33—C32—H32	119.5
C12—C11—H11	119.3	C28—C33—C32	120.1 (4)
C10—C11—H11	119.3	C28—C33—H33	119.9
C13—C12—C11	120.7 (3)	C32—C33—H33	119.9
C13—C12—H12	119.7	C19—C34—H34A	109.5
C11—C12—H12	119.7	C19—C34—H34B	109.5
C12—C13—C14	119.9 (4)	H34A—C34—H34B	109.5
C12—C13—Cl1	120.5 (3)	C19—C34—H34C	109.5
C14—C13—Cl1	119.5 (3)	H34A—C34—H34C	109.5
C13—C14—C15	119.3 (3)	H34B—C34—H34C	109.5
C13—C14—H14	120.4	C31—C35—H35A	109.5
C15—C14—H14	120.4	C31—C35—H35B	109.5
C14—C15—C10	121.7 (3)	H35A—C35—H35B	109.5
C14—C15—H15	119.2	C31—C35—H35C	109.5
C10—C15—H15	119.2	H35A—C35—H35C	109.5
N1—C16—C21	121.6 (3)	H35B—C35—H35C	109.5
C16—N1—C2—C3	149.8 (3)	C2—C10—C15—C14	176.6 (3)
C6—N1—C2—C3	−32.9 (4)	C6—N1—C16—C21	12.6 (4)
C16—N1—C2—C10	−82.0 (3)	C2—N1—C16—C21	−170.0 (3)
C6—N1—C2—C10	95.3 (3)	C6—N1—C16—C17	−166.2 (3)
N1—C2—C3—C4	44.2 (4)	C2—N1—C16—C17	11.2 (4)
C10—C2—C3—C4	−84.6 (3)	N1—C16—C17—C18	178.8 (3)
N1—C2—C3—C7	−133.7 (3)	C21—C16—C17—C18	0.0 (5)
C10—C2—C3—C7	97.6 (4)	C16—C17—C18—C19	−0.5 (5)
C28—N2—C4—C3	164.0 (3)	C17—C18—C19—C20	0.6 (5)
C28—N2—C4—C5	−14.7 (5)	C17—C18—C19—C34	−177.6 (3)
C7—C3—C4—N2	−3.8 (5)	C18—C19—C20—C21	−0.2 (5)
C2—C3—C4—N2	178.3 (3)	C34—C19—C20—C21	178.0 (3)
C7—C3—C4—C5	174.9 (3)	C19—C20—C21—C16	−0.3 (5)
C2—C3—C4—C5	−3.0 (4)	N1—C16—C21—C20	−178.4 (3)
N2—C4—C5—C6	131.0 (3)	C17—C16—C21—C20	0.4 (4)
C3—C4—C5—C6	−47.9 (4)	N1—C6—C22—C23	−28.6 (4)
C16—N1—C6—C22	−73.9 (3)	C5—C6—C22—C23	95.9 (3)
C2—N1—C6—C22	108.7 (3)	N1—C6—C22—C27	154.7 (3)
C16—N1—C6—C5	161.4 (2)	C5—C6—C22—C27	−80.8 (3)
C2—N1—C6—C5	−16.0 (4)	C27—C22—C23—C24	1.2 (5)
C4—C5—C6—N1	56.5 (3)	C6—C22—C23—C24	−175.6 (3)
C4—C5—C6—C22	−70.6 (3)	C22—C23—C24—C25	−0.7 (5)
C8—O2—C7—O1	3.0 (5)	C23—C24—C25—C26	−1.0 (5)
C8—O2—C7—C3	−176.3 (3)	C23—C24—C25—Cl2	179.4 (2)
C4—C3—C7—O1	5.2 (5)	C24—C25—C26—C27	2.2 (5)
C2—C3—C7—O1	−177.0 (3)	Cl2—C25—C26—C27	−178.3 (2)
C4—C3—C7—O2	−175.6 (3)	C25—C26—C27—C22	−1.7 (5)
C2—C3—C7—O2	2.2 (4)	C23—C22—C27—C26	0.0 (4)
C7—O2—C8—C9	174.9 (3)	C6—C22—C27—C26	176.9 (3)
N1—C2—C10—C11	−172.4 (3)	C4—N2—C28—C29	100.0 (4)
C3—C2—C10—C11	−44.8 (4)	C4—N2—C28—C33	−79.7 (5)
N1—C2—C10—C15	10.7 (4)	C33—C28—C29—C30	−1.2 (6)
C3—C2—C10—C15	138.3 (3)	N2—C28—C29—C30	179.1 (3)
C15—C10—C11—C12	−0.1 (5)	C28—C29—C30—C31	0.7 (6)
C2—C10—C11—C12	−177.2 (3)	C29—C30—C31—C32	−0.6 (7)
C10—C11—C12—C13	0.4 (5)	C29—C30—C31—C35	−179.8 (4)
C11—C12—C13—C14	−0.2 (6)	C30—C31—C32—C33	0.8 (6)
C11—C12—C13—Cl1	178.9 (3)	C35—C31—C32—C33	−179.9 (4)
C12—C13—C14—C15	−0.3 (5)	C29—C28—C33—C32	1.4 (6)
Cl1—C13—C14—C15	−179.4 (3)	N2—C28—C33—C32	−178.8 (3)
C13—C14—C15—C10	0.6 (5)	C31—C32—C33—C28	−1.3 (6)
C11—C10—C15—C14	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.10	2.707 (4)	127
C9—H9A···Cl2i	0.96	2.74	3.698 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.10	2.707 (4)	127
C9—H9A⋯Cl2i	0.96	2.74	3.698 (4)	173

Symmetry code: (i) .