N-(2,6-Diisopropyl­phen­yl)-6-[(2,6-di­isopropyl­phen­yl)(methacrylo­yl)amino­carbon­yl]pyridine-2-carboximidoyl chloride

Aydın, A.; Dinçer, M.; Dayan, O.; Çetinkaya, B.

doi:10.1107/S1600536807053901

N-(2,6-Diisopropylphenyl)-6-[(2,6-diisopropylphenyl)(methacryloyl)aminocarbonyl]pyridine-2-carboximidoyl chloride

A. Aydın, M. Dinçer, O. Dayan and B. Çetinkaya

In the title compound, C₃₅H₄₂ClN₃O₂, molecules are linked to one another by intermolecular C—H

O interactions, forming a C(12) chain running parallel to the [010] direction. The molecule has a nonplanar conformation. The benzene rings make dihedral angles of 72.72 (6) and 62.72 (6)° with the pyridine ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053901/om2180sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053901/om2180Isup2.hkl Contains datablock I

CCDC reference: 672814

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.046
wR factor = 0.142
Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C33

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.127
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.69 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      39.00 A   3 

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Imide functionality is found as a basic structural element in a wide range of naturally occurring compounds such as uracil and thymine. Moreover, many imide-containing unnatural products have been prepared to test the pharmacological properties as well as their structural properties (Bacha et al., 1987; Sladowska et al., 1995). Imidoyl chlorides react with carboxylic acids and their salts, yielding N-substitue imides with regard to Mumm rearrangement reaction (Bonnett, 1970; Shishkin et al., 2004)

Proceeding with our research into pyridyl containing moties (Dayan & Çetinkaya, 2005), we have studied utility of the above reaction for preparing new functionally substituted pyridine derivatives. In this work, we synthesized (II) from N,N'-bis(2,6-diisopropylphenyl)pyridine-2,6-dicarboximidoyl dichloride, (I), with sodium methacrylat in THF. The title compound was characterized by elemental analysis, spectroscopic and X-ray crystallographic methods.

The structure of the title compound, (II), is shown in Fig. 1 and selected geometric parameters are listed in Table 1. The interatomic distances and angles show no anomalies. In the molecular structure of (II), (C7—C12) and (C24—C29) phenyl rings make dihedral angles of 72.72 (6) and 62.72 (6)°, respectively, with the pyridine ring.

In the crystal structure of (II), atom C14 in the molecule at (x, y, z) acts as hydrogen-bond donor to the O atom in the molecule at (-x, y + 1/2, -z + 1/2), forming a C(12) (Bernstein et al., 1995) chain running parallel to the [010] direction.

Related literature top

For related literature, see: Archer et al. (2006); Bacha et al. (1987); Bernstein et al. (1995); Bonnett (1970); Dayan & Çetinkaya (2005); Shishkin et al. (2004); Sladowska et al. (1995).

Experimental top

(I) was prepared a modification of literature method (Archer et al., 2006). A mixture of (I) (523 mg, 1 mmol) and sodium methacrylat (106 mg, 1 mmol) were refluxed in THF (20 ml) for 2 days and was concentrated (5 ml). Et₂O was added with stirring to a final volume of 20 ml causing a yellow powder to precipitate. The precipitate was filtered off, washed with Et₂O and dried. X-ray quality crystals were grown from CH₂Cl₂-hexane (1:2 v/v, 30 ml) (yield: 410 mg, 72%; m.p. 404–405 K). Analysis calculated for C₃₅H₄₂ClN₃O₂: C 73.47, H 7.40, N 7.34%; found: C 73.23, H 7.49, N 7.32%. ¹H NMR (CDCl₃): δ 8.32 (d, J = 8.0, 1H, py—Hm), 7.99 (d, J = 7.6, 1H, py—Hm), 7.94 (t, J = 7.6, 1H, py—Hp), 7.18–7.13 [m, 6H, (CH₃)₂CH—C₆H₃], 5.48 (s, 1H, CH₂-acryl), 5.12 (s, 1H, CH₂-acryl), 2.79–2.66 [m, 4H, (CH₃)₂CH—C₆H₃], 1.74 (s, 3H, CH₃-acryl), 1.16–1.05 [m, 24H, (CH₃)₂CH—C₆H₃]; ¹³C NMR (CDCl₃): δ 176.75, 168.33, 164.17, 159.49, 155.38, 149.27, 147.86, 145.28, 139.37, 136.14, 132.65; 130.29, 127.35, 126.03, 125.44, 118.14, 112.76, 29.91, 27.75, 22.44, 20.20.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. : A view of (II), with 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms have been omitted for clarity.
	Fig. 2. : A packing diagram of (II), viewed approximately along the a axis. For clarity, only H atoms involved in hydrogen bonding have been included.
	Fig. 3. The formation of the title compound.

N-(2,6-Diisopropylphenyl)-6-[(2,6- diisopropylphenyl)(methacryloyl)aminocarbonyl]pyridine-2-carboximidoyl chloride top

Crystal data top

C₃₅H₄₂ClN₃O₂	F(000) = 1224
M_r = 572.17	D_x = 1.144 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 35523 reflections
a = 9.4568 (3) Å	θ = 1.4–27.3°
b = 14.6356 (7) Å	µ = 0.15 mm⁻¹
c = 24.0095 (8) Å	T = 296 K
β = 91.391 (3)°	Prism, colorless
V = 3322.1 (2) Å³	0.69 × 0.58 × 0.30 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	7398 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4940 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.127
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.3°, θ_min = 1.6°
w scans	h = −12→12
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	k = −18→18
T_min = 0.917, T_max = 0.960	l = −30→30
52993 measured reflections

Refinement top

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0692P)² + 0.1358P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
7398 reflections	Δρ_max = 0.19 e Å⁻³
380 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (10)

Crystal data top

C₃₅H₄₂ClN₃O₂	V = 3322.1 (2) Å³
M_r = 572.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4568 (3) Å	µ = 0.15 mm⁻¹
b = 14.6356 (7) Å	T = 296 K
c = 24.0095 (8) Å	0.69 × 0.58 × 0.30 mm
β = 91.391 (3)°

Data collection top

STOE IPDS 2 diffractometer	7398 independent reflections
Absorption correction: integration X-RED32 (Stoe & Cie, 2002)	4940 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.960	R_int = 0.127
52993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
7398 reflections	Δρ_min = −0.30 e Å⁻³
380 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.09937 (5)	0.11683 (5)	0.130226 (18)	0.0925 (2)
O1	0.09310 (12)	0.09776 (10)	0.38351 (4)	0.0686 (3)
O2	0.39007 (13)	0.20674 (11)	0.25418 (6)	0.0835 (4)
N1	0.01045 (12)	0.14281 (9)	0.24386 (5)	0.0471 (3)
N2	−0.16629 (14)	0.16848 (10)	0.11306 (5)	0.0559 (3)
N3	0.24640 (12)	0.14538 (9)	0.31830 (5)	0.0489 (3)
C1	−0.01507 (14)	0.13968 (10)	0.29816 (5)	0.0457 (3)
C2	−0.14984 (15)	0.13780 (12)	0.31944 (6)	0.0562 (4)
H2	−0.1631	0.1347	0.3576	0.067*
C3	−0.26403 (16)	0.14068 (14)	0.28249 (7)	0.0646 (4)
H3	−0.3560	0.1401	0.2954	0.078*
C4	−0.23943 (16)	0.14445 (12)	0.22635 (6)	0.0599 (4)
H4	−0.3145	0.1468	0.2007	0.072*
C5	−0.10126 (15)	0.14471 (11)	0.20865 (6)	0.0483 (3)
C6	−0.07281 (16)	0.14728 (11)	0.14799 (6)	0.0532 (4)
C7	−0.14697 (16)	0.16956 (12)	0.05439 (6)	0.0560 (4)
C8	−0.10439 (18)	0.25004 (13)	0.02938 (7)	0.0632 (4)
C9	−0.0905 (2)	0.24901 (15)	−0.02835 (8)	0.0747 (5)
H9	−0.0597	0.3015	−0.0462	0.090*
C10	−0.1208 (2)	0.17306 (16)	−0.05911 (7)	0.0771 (5)
H10	−0.1105	0.1742	−0.0975	0.092*
C11	−0.16686 (19)	0.09442 (14)	−0.03359 (7)	0.0694 (5)
H11	−0.1886	0.0433	−0.0551	0.083*
C12	−0.18114 (17)	0.09059 (12)	0.02394 (6)	0.0589 (4)
C13	−0.0822 (2)	0.33733 (15)	0.06249 (8)	0.0767 (5)
H13	−0.0890	0.3212	0.1019	0.092*
C14	−0.1990 (4)	0.4046 (2)	0.04950 (17)	0.1455 (14)
H14A	−0.1831	0.4595	0.0706	0.218*
H14B	−0.2882	0.3784	0.0592	0.218*
H14C	−0.2002	0.4187	0.0104	0.218*
C15	0.0599 (3)	0.3802 (2)	0.05534 (16)	0.1359 (11)
H15A	0.1325	0.3359	0.0634	0.204*
H15B	0.0705	0.4310	0.0804	0.204*
H15C	0.0679	0.4011	0.0177	0.204*
C16	−0.2335 (2)	0.00589 (14)	0.05299 (7)	0.0694 (5)
H16	−0.1710	−0.0042	0.0856	0.083*
C17	−0.2292 (2)	−0.08059 (15)	0.01778 (9)	0.0822 (6)
H17A	−0.2963	−0.0755	−0.0127	0.123*
H17B	−0.2527	−0.1324	0.0403	0.123*
H17C	−0.1360	−0.0884	0.0036	0.123*
C18	−0.3825 (2)	0.0218 (2)	0.07462 (10)	0.1040 (8)
H18A	−0.3843	0.0778	0.0954	0.156*
H18B	−0.4082	−0.0281	0.0983	0.156*
H18C	−0.4486	0.0256	0.0437	0.156*
C19	0.10994 (15)	0.12868 (11)	0.33765 (6)	0.0486 (3)
C20	0.28190 (16)	0.21303 (12)	0.28020 (7)	0.0579 (4)
C21	0.19384 (17)	0.29727 (13)	0.27667 (8)	0.0635 (4)
C22	0.1475 (2)	0.33563 (15)	0.32245 (10)	0.0847 (6)
H22A	0.1698	0.3101	0.3570	0.102*
H22B	0.0925	0.3882	0.3202	0.102*
C23	0.1784 (2)	0.33936 (17)	0.21987 (10)	0.0918 (7)
H23A	0.1072	0.3071	0.1986	0.138*
H23B	0.2669	0.3357	0.2013	0.138*
H23C	0.1512	0.4023	0.2234	0.138*
C24	0.35683 (14)	0.08216 (11)	0.33730 (6)	0.0514 (4)
C25	0.37940 (16)	0.00325 (12)	0.30608 (7)	0.0603 (4)
C26	0.4819 (2)	−0.05741 (14)	0.32601 (8)	0.0748 (5)
H26	0.4983	−0.1112	0.3066	0.090*
C27	0.5593 (2)	−0.03942 (15)	0.37385 (8)	0.0784 (5)
H27	0.6276	−0.0808	0.3863	0.094*
C28	0.53648 (18)	0.03889 (14)	0.40326 (7)	0.0694 (5)
H28	0.5908	0.0503	0.4353	0.083*
C29	0.43408 (15)	0.10189 (12)	0.38640 (6)	0.0558 (4)
C30	0.41205 (17)	0.18827 (13)	0.41938 (7)	0.0632 (4)
H30	0.3209	0.2145	0.4074	0.076*
C31	0.4057 (4)	0.1689 (2)	0.48191 (9)	0.1244 (11)
H31A	0.4974	0.1503	0.4957	0.187*
H31B	0.3387	0.1210	0.4883	0.187*
H31C	0.3770	0.2232	0.5010	0.187*
C32	0.5241 (3)	0.2564 (2)	0.40716 (16)	0.1345 (12)
H32A	0.6154	0.2297	0.4143	0.202*
H32B	0.5129	0.3090	0.4305	0.202*
H32C	0.5161	0.2744	0.3688	0.202*
C33	0.29733 (19)	−0.01790 (15)	0.25266 (8)	0.0737 (5)
H33	0.2347	0.0340	0.2445	0.088*
C34	0.2056 (4)	−0.1009 (3)	0.26082 (17)	0.1589 (15)
H34A	0.2645	−0.1531	0.2686	0.238*
H34B	0.1498	−0.1119	0.2276	0.238*
H34C	0.1443	−0.0907	0.2915	0.238*
C35	0.3943 (3)	−0.0290 (3)	0.20401 (10)	0.1347 (13)
H35A	0.4535	−0.0815	0.2100	0.202*
H35B	0.4522	0.0246	0.2008	0.202*
H35C	0.3387	−0.0369	0.1704	0.202*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0634 (3)	0.1692 (6)	0.0451 (2)	0.0331 (3)	0.00353 (18)	−0.0044 (3)
O1	0.0563 (6)	0.1064 (10)	0.0430 (6)	0.0093 (6)	0.0030 (4)	0.0161 (6)
O2	0.0544 (7)	0.1148 (11)	0.0822 (9)	0.0067 (7)	0.0181 (6)	0.0299 (8)
N1	0.0421 (6)	0.0611 (7)	0.0381 (6)	0.0008 (5)	0.0001 (4)	−0.0001 (5)
N2	0.0548 (7)	0.0726 (9)	0.0401 (6)	−0.0004 (6)	−0.0028 (5)	0.0022 (6)
N3	0.0395 (6)	0.0654 (8)	0.0416 (6)	0.0044 (5)	−0.0010 (4)	0.0027 (5)
C1	0.0421 (7)	0.0565 (8)	0.0385 (7)	0.0017 (6)	0.0004 (5)	0.0004 (6)
C2	0.0461 (7)	0.0816 (11)	0.0412 (7)	0.0022 (7)	0.0041 (6)	0.0002 (7)
C3	0.0407 (7)	0.1008 (14)	0.0525 (9)	−0.0005 (8)	0.0038 (6)	0.0018 (8)
C4	0.0436 (7)	0.0867 (12)	0.0489 (8)	−0.0004 (7)	−0.0055 (6)	0.0009 (8)
C5	0.0466 (7)	0.0592 (9)	0.0387 (7)	0.0007 (6)	−0.0025 (5)	−0.0001 (6)
C6	0.0507 (8)	0.0675 (10)	0.0412 (7)	0.0001 (7)	−0.0018 (6)	−0.0013 (6)
C7	0.0513 (8)	0.0770 (11)	0.0395 (7)	0.0052 (7)	−0.0044 (6)	0.0030 (7)
C8	0.0645 (9)	0.0779 (12)	0.0471 (9)	0.0007 (8)	−0.0032 (7)	0.0066 (8)
C9	0.0806 (12)	0.0917 (14)	0.0518 (10)	0.0041 (10)	0.0025 (8)	0.0185 (9)
C10	0.0862 (13)	0.1055 (16)	0.0395 (8)	0.0164 (11)	0.0026 (8)	0.0071 (9)
C11	0.0728 (11)	0.0901 (13)	0.0449 (9)	0.0129 (10)	−0.0040 (7)	−0.0050 (8)
C12	0.0547 (8)	0.0772 (11)	0.0446 (8)	0.0080 (8)	−0.0051 (6)	−0.0004 (7)
C13	0.0839 (13)	0.0801 (13)	0.0657 (11)	−0.0125 (10)	−0.0071 (9)	0.0064 (9)
C14	0.122 (2)	0.112 (2)	0.200 (4)	0.0292 (19)	−0.053 (2)	−0.067 (2)
C15	0.098 (2)	0.139 (3)	0.170 (3)	−0.0331 (18)	−0.0128 (19)	−0.017 (2)
C16	0.0714 (11)	0.0835 (13)	0.0530 (9)	−0.0095 (9)	−0.0034 (8)	−0.0004 (8)
C17	0.0827 (13)	0.0812 (13)	0.0825 (14)	−0.0009 (11)	−0.0039 (10)	−0.0046 (10)
C18	0.0911 (15)	0.122 (2)	0.1003 (17)	−0.0290 (14)	0.0295 (13)	−0.0287 (15)
C19	0.0445 (7)	0.0635 (9)	0.0378 (7)	0.0056 (6)	0.0016 (5)	0.0014 (6)
C20	0.0453 (8)	0.0755 (11)	0.0528 (8)	−0.0019 (7)	−0.0015 (6)	0.0086 (8)
C21	0.0506 (8)	0.0660 (10)	0.0732 (11)	−0.0072 (7)	−0.0093 (7)	0.0122 (9)
C22	0.0927 (15)	0.0691 (12)	0.0911 (15)	0.0129 (11)	−0.0228 (11)	−0.0079 (11)
C23	0.0740 (12)	0.1016 (16)	0.0997 (16)	−0.0031 (11)	−0.0011 (11)	0.0470 (13)
C24	0.0403 (7)	0.0656 (9)	0.0482 (8)	0.0057 (6)	−0.0001 (6)	0.0030 (7)
C25	0.0486 (8)	0.0730 (11)	0.0593 (9)	0.0068 (7)	0.0017 (7)	−0.0054 (8)
C26	0.0680 (11)	0.0775 (12)	0.0787 (12)	0.0210 (9)	−0.0015 (9)	−0.0070 (10)
C27	0.0665 (11)	0.0895 (14)	0.0788 (13)	0.0285 (10)	−0.0066 (9)	0.0053 (11)
C28	0.0574 (9)	0.0916 (13)	0.0586 (10)	0.0159 (9)	−0.0093 (7)	0.0053 (9)
C29	0.0463 (7)	0.0745 (11)	0.0466 (8)	0.0061 (7)	−0.0016 (6)	0.0027 (7)
C30	0.0539 (9)	0.0840 (12)	0.0511 (9)	0.0065 (8)	−0.0091 (7)	−0.0045 (8)
C31	0.175 (3)	0.145 (2)	0.0532 (12)	0.058 (2)	0.0017 (14)	−0.0095 (13)
C32	0.108 (2)	0.107 (2)	0.191 (3)	−0.0304 (16)	0.042 (2)	−0.052 (2)
C33	0.0630 (10)	0.0879 (13)	0.0697 (11)	0.0122 (9)	−0.0074 (8)	−0.0244 (10)
C34	0.153 (3)	0.158 (3)	0.163 (3)	−0.068 (3)	−0.055 (2)	−0.008 (2)
C35	0.0994 (18)	0.230 (4)	0.0745 (15)	0.033 (2)	−0.0008 (13)	−0.053 (2)

Geometric parameters (Å, º) top

Cl1—C6	1.7508 (16)	C17—H17B	0.9600
O1—C19	1.2046 (17)	C17—H17C	0.9600
O2—C20	1.2150 (19)	C18—H18A	0.9600
N1—C1	1.3325 (17)	C18—H18B	0.9600
N1—C5	1.3372 (17)	C18—H18C	0.9600
N2—C6	1.2431 (19)	C20—C21	1.489 (3)
N2—C7	1.4251 (19)	C21—C22	1.318 (3)
N3—C20	1.395 (2)	C21—C23	1.500 (3)
N3—C19	1.4035 (18)	C22—H22A	0.9300
N3—C24	1.4599 (18)	C22—H22B	0.9300
C1—C2	1.385 (2)	C23—H23A	0.9600
C1—C19	1.5060 (18)	C23—H23B	0.9600
C2—C3	1.382 (2)	C23—H23C	0.9600
C2—H2	0.9300	C24—C25	1.396 (2)
C3—C4	1.374 (2)	C24—C29	1.402 (2)
C3—H3	0.9300	C25—C26	1.391 (2)
C4—C5	1.384 (2)	C25—C33	1.515 (2)
C4—H4	0.9300	C26—C27	1.372 (3)
C5—C6	1.488 (2)	C26—H26	0.9300
C7—C8	1.386 (2)	C27—C28	1.366 (3)
C7—C12	1.401 (2)	C27—H27	0.9300
C8—C9	1.396 (2)	C28—C29	1.390 (2)
C8—C13	1.517 (3)	C28—H28	0.9300
C9—C10	1.361 (3)	C29—C30	1.509 (2)
C9—H9	0.9300	C30—C32	1.489 (3)
C10—C11	1.379 (3)	C30—C31	1.530 (3)
C10—H10	0.9300	C30—H30	0.9800
C11—C12	1.392 (2)	C31—H31A	0.9600
C11—H11	0.9300	C31—H31B	0.9600
C12—C16	1.512 (3)	C31—H31C	0.9600
C13—C15	1.497 (3)	C32—H32A	0.9600
C13—C14	1.507 (4)	C32—H32B	0.9600
C13—H13	0.9800	C32—H32C	0.9600
C14—H14A	0.9600	C33—C34	1.509 (4)
C14—H14B	0.9600	C33—C35	1.511 (3)
C14—H14C	0.9600	C33—H33	0.9800
C15—H15A	0.9600	C34—H34A	0.9600
C15—H15B	0.9600	C34—H34B	0.9600
C15—H15C	0.9600	C34—H34C	0.9600
C16—C17	1.523 (3)	C35—H35A	0.9600
C16—C18	1.532 (3)	C35—H35B	0.9600
C16—H16	0.9800	C35—H35C	0.9600
C17—H17A	0.9600

C1—N1—C5	117.40 (12)	H18A—C18—H18C	109.5
C6—N2—C7	124.30 (14)	H18B—C18—H18C	109.5
C20—N3—C19	125.35 (12)	O1—C19—N3	120.72 (12)
C20—N3—C24	118.24 (12)	O1—C19—C1	119.76 (13)
C19—N3—C24	116.28 (12)	N3—C19—C1	119.15 (12)
N1—C1—C2	123.50 (13)	O2—C20—N3	120.17 (16)
N1—C1—C19	117.49 (12)	O2—C20—C21	120.68 (16)
C2—C1—C19	118.75 (12)	N3—C20—C21	118.82 (14)
C3—C2—C1	118.32 (14)	C22—C21—C20	120.12 (17)
C3—C2—H2	120.8	C22—C21—C23	123.8 (2)
C1—C2—H2	120.8	C20—C21—C23	115.70 (18)
C4—C3—C2	118.86 (14)	C21—C22—H22A	120.0
C4—C3—H3	120.6	C21—C22—H22B	120.0
C2—C3—H3	120.6	H22A—C22—H22B	120.0
C3—C4—C5	119.01 (13)	C21—C23—H23A	109.5
C3—C4—H4	120.5	C21—C23—H23B	109.5
C5—C4—H4	120.5	H23A—C23—H23B	109.5
N1—C5—C4	122.90 (13)	C21—C23—H23C	109.5
N1—C5—C6	117.41 (12)	H23A—C23—H23C	109.5
C4—C5—C6	119.69 (12)	H23B—C23—H23C	109.5
N2—C6—C5	121.61 (14)	C25—C24—C29	122.59 (14)
N2—C6—Cl1	123.33 (12)	C25—C24—N3	118.30 (13)
C5—C6—Cl1	115.05 (10)	C29—C24—N3	119.10 (14)
C8—C7—C12	122.73 (14)	C26—C25—C24	117.24 (15)
C8—C7—N2	118.88 (15)	C26—C25—C33	119.96 (16)
C12—C7—N2	118.25 (15)	C24—C25—C33	122.80 (15)
C7—C8—C9	117.14 (17)	C27—C26—C25	121.23 (18)
C7—C8—C13	121.79 (15)	C27—C26—H26	119.4
C9—C8—C13	120.96 (17)	C25—C26—H26	119.4
C10—C9—C8	121.60 (18)	C28—C27—C26	120.40 (17)
C10—C9—H9	119.2	C28—C27—H27	119.8
C8—C9—H9	119.2	C26—C27—H27	119.8
C9—C10—C11	120.33 (16)	C27—C28—C29	121.56 (16)
C9—C10—H10	119.8	C27—C28—H28	119.2
C11—C10—H10	119.8	C29—C28—H28	119.2
C10—C11—C12	120.90 (18)	C28—C29—C24	116.97 (16)
C10—C11—H11	119.5	C28—C29—C30	120.46 (14)
C12—C11—H11	119.5	C24—C29—C30	122.56 (14)
C11—C12—C7	117.24 (17)	C32—C30—C29	110.45 (17)
C11—C12—C16	122.11 (16)	C32—C30—C31	111.2 (2)
C7—C12—C16	120.64 (14)	C29—C30—C31	111.64 (18)
C15—C13—C14	111.0 (2)	C32—C30—H30	107.8
C15—C13—C8	114.0 (2)	C29—C30—H30	107.8
C14—C13—C8	110.51 (17)	C31—C30—H30	107.8
C15—C13—H13	107.0	C30—C31—H31A	109.5
C14—C13—H13	107.0	C30—C31—H31B	109.5
C8—C13—H13	107.0	H31A—C31—H31B	109.5
C13—C14—H14A	109.5	C30—C31—H31C	109.5
C13—C14—H14B	109.5	H31A—C31—H31C	109.5
H14A—C14—H14B	109.5	H31B—C31—H31C	109.5
C13—C14—H14C	109.5	C30—C32—H32A	109.5
H14A—C14—H14C	109.5	C30—C32—H32B	109.5
H14B—C14—H14C	109.5	H32A—C32—H32B	109.5
C13—C15—H15A	109.5	C30—C32—H32C	109.5
C13—C15—H15B	109.5	H32A—C32—H32C	109.5
H15A—C15—H15B	109.5	H32B—C32—H32C	109.5
C13—C15—H15C	109.5	C34—C33—C35	112.1 (3)
H15A—C15—H15C	109.5	C34—C33—C25	109.8 (2)
H15B—C15—H15C	109.5	C35—C33—C25	111.61 (17)
C12—C16—C17	114.32 (15)	C34—C33—H33	107.7
C12—C16—C18	110.27 (18)	C35—C33—H33	107.7
C17—C16—C18	110.57 (17)	C25—C33—H33	107.7
C12—C16—H16	107.1	C33—C34—H34A	109.5
C17—C16—H16	107.1	C33—C34—H34B	109.5
C18—C16—H16	107.1	H34A—C34—H34B	109.5
C16—C17—H17A	109.5	C33—C34—H34C	109.5
C16—C17—H17B	109.5	H34A—C34—H34C	109.5
H17A—C17—H17B	109.5	H34B—C34—H34C	109.5
C16—C17—H17C	109.5	C33—C35—H35A	109.5
H17A—C17—H17C	109.5	C33—C35—H35B	109.5
H17B—C17—H17C	109.5	H35A—C35—H35B	109.5
C16—C18—H18A	109.5	C33—C35—H35C	109.5
C16—C18—H18B	109.5	H35A—C35—H35C	109.5
H18A—C18—H18B	109.5	H35B—C35—H35C	109.5
C16—C18—H18C	109.5

C5—N1—C1—C2	0.4 (2)	C24—N3—C19—O1	33.8 (2)
C5—N1—C1—C19	174.43 (13)	C20—N3—C19—C1	36.5 (2)
N1—C1—C2—C3	−1.0 (3)	C24—N3—C19—C1	−139.26 (14)
C19—C1—C2—C3	−174.97 (16)	N1—C1—C19—O1	−157.08 (15)
C1—C2—C3—C4	0.6 (3)	C2—C1—C19—O1	17.3 (2)
C2—C3—C4—C5	0.4 (3)	N1—C1—C19—N3	16.1 (2)
C1—N1—C5—C4	0.6 (2)	C2—C1—C19—N3	−169.59 (14)
C1—N1—C5—C6	−179.41 (13)	C19—N3—C20—O2	−159.05 (16)
C3—C4—C5—N1	−1.0 (3)	C24—N3—C20—O2	16.6 (2)
C3—C4—C5—C6	179.04 (16)	C19—N3—C20—C21	27.6 (2)
C7—N2—C6—C5	−178.02 (15)	C24—N3—C20—C21	−156.76 (14)
C7—N2—C6—Cl1	1.0 (2)	O2—C20—C21—C22	−132.8 (2)
N1—C5—C6—N2	−164.47 (16)	N3—C20—C21—C22	40.5 (2)
C4—C5—C6—N2	15.5 (2)	O2—C20—C21—C23	40.1 (2)
N1—C5—C6—Cl1	16.44 (19)	N3—C20—C21—C23	−146.60 (16)
C4—C5—C6—Cl1	−163.61 (13)	C20—N3—C24—C25	−87.66 (18)
C6—N2—C7—C8	−91.8 (2)	C19—N3—C24—C25	88.37 (17)
C6—N2—C7—C12	92.4 (2)	C20—N3—C24—C29	93.46 (17)
C12—C7—C8—C9	−2.7 (3)	C19—N3—C24—C29	−90.50 (17)
N2—C7—C8—C9	−178.26 (15)	C29—C24—C25—C26	0.9 (2)
C12—C7—C8—C13	173.73 (16)	N3—C24—C25—C26	−177.90 (15)
N2—C7—C8—C13	−1.9 (2)	C29—C24—C25—C33	−179.32 (16)
C7—C8—C9—C10	1.7 (3)	N3—C24—C25—C33	1.9 (2)
C13—C8—C9—C10	−174.77 (18)	C24—C25—C26—C27	−1.2 (3)
C8—C9—C10—C11	0.1 (3)	C33—C25—C26—C27	179.06 (19)
C9—C10—C11—C12	−1.0 (3)	C25—C26—C27—C28	0.3 (3)
C10—C11—C12—C7	0.0 (2)	C26—C27—C28—C29	0.8 (3)
C10—C11—C12—C16	179.02 (17)	C27—C28—C29—C24	−1.0 (3)
C8—C7—C12—C11	1.9 (2)	C27—C28—C29—C30	−179.43 (18)
N2—C7—C12—C11	177.47 (14)	C25—C24—C29—C28	0.2 (2)
C8—C7—C12—C16	−177.16 (16)	N3—C24—C29—C28	178.97 (14)
N2—C7—C12—C16	−1.6 (2)	C25—C24—C29—C30	178.50 (15)
C7—C8—C13—C15	126.6 (2)	N3—C24—C29—C30	−2.7 (2)
C9—C8—C13—C15	−57.2 (3)	C28—C29—C30—C32	77.9 (3)
C7—C8—C13—C14	−107.6 (3)	C24—C29—C30—C32	−100.4 (2)
C9—C8—C13—C14	68.7 (3)	C28—C29—C30—C31	−46.5 (2)
C11—C12—C16—C17	16.3 (2)	C24—C29—C30—C31	135.2 (2)
C7—C12—C16—C17	−164.71 (16)	C26—C25—C33—C34	66.1 (3)
C11—C12—C16—C18	−108.98 (19)	C24—C25—C33—C34	−113.6 (3)
C7—C12—C16—C18	70.0 (2)	C26—C25—C33—C35	−58.8 (3)
C20—N3—C19—O1	−150.47 (16)	C24—C25—C33—C35	121.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.96	2.45	3.392 (3)	168

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₅H₄₂ClN₃O₂
M_r	572.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.4568 (3), 14.6356 (7), 24.0095 (8)
β (°)	91.391 (3)
V (Å³)	3322.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.69 × 0.58 × 0.30

Data collection
Diffractometer	STOE IPDS 2 diffractometer
Absorption correction	Integration X-RED32 (Stoe & Cie, 2002)
T_min, T_max	0.917, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	52993, 7398, 4940
R_int	0.127
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.142, 1.06
No. of reflections	7398
No. of parameters	380
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.30

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Cl1—C6	1.7508 (16)	N3—C20	1.395 (2)
O1—C19	1.2046 (17)	N3—C19	1.4035 (18)
O2—C20	1.2150 (19)	N3—C24	1.4599 (18)
N2—C6	1.2431 (19)	C1—C19	1.5060 (18)
N2—C7	1.4251 (19)	C5—C6	1.488 (2)

C6—N2—C7	124.30 (14)	C19—N3—C24	116.28 (12)
C20—N3—C19	125.35 (12)	N2—C6—Cl1	123.33 (12)
C20—N3—C24	118.24 (12)	C5—C6—Cl1	115.05 (10)

C7—N2—C6—C5	−178.02 (15)	C24—N3—C19—C1	−139.26 (14)