4-[Bis(2-methyl-1H-indol-3-yl)meth­yl]-1-(4-methoxy­phen­yl)-3-phenyl­azetidin-2-one

In the title compound, C₃₅H₃₁N₃O₂, the dihedral angle between the two indole groups is 76.4 (1)°. The mol­ecular structure is stabilized by an intra­molecular π–π inter­action. The mol­ecular packing in the crystal structure is stabilized by strong N—H...O hydrogen bonds and weak N—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.148
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C33    -   C34     ..       6.39 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C34    -   C35     ..       5.83 su

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

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

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S1. Comment

The importance and structural diversity of biologically active β-lactam antibiotics, the most widely employed family of antimicrobial agents to date, accounting for 50% of the world's total antibiotic market, led to the development of efficient approaches for the construction of appropriately substituted 2-azetidinones (Alcaide et al., 2000). The minimum structural features believed to be essential for antimicrobial activity in the β-lactams antibiotics have undergone considerable revision, since in recent years several natural monocyclic β-lactams were shown to exhibit high antibacterial activity. Now it seems that the minimum requirement for biological activity is a suitably substituted monocyclic 2-azetidinone ring (Page, 1984). Indole, being an integral part of many natural products of therapeutic importance, possesses potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). In view of its importance and to obtain more detailed information on the structural conformation of the molecule, the crystal structure of the title cxompound, (I), was determined.

The molecular structure of (I) is illustrated in Fig. 1. Selected geometric parameters are presented in Table 1. Compound (I) consists of two indole moieties, a β-lactam ring, a methoxyphenyl ring and a phenyl ring. The geometry of the β-lactam ring is comparable to the related reported structure (Ercan et al., 1996; Ülkü et al., 1997). The two indole rings have bond distances and angles comparable to those reported for other indole derivatives (Karthick et al., 2005; Sonar et al., 2005).

The exocyclic angles around atom C7 show considerable asymmetry, O2—C7—C6 [124.8 (1)°] being wider than O2—C7—C8 [116.0 (1)°]. This difference is due to steric repulsion between the phenyl ring and the methyl group. The torsion angles C10—O2—C7—C6 [−0.1 (2)°] and C10—O2—C7—C8 [−180.0 (2)°] indicate that the methyl group does not deviate significantly from the plane of the attached benzene ring. The two indole moieties enclose a dihedral angle of 76.4 (1)°. The phenyl ring and the methoxyphenyl ring enclose a dihedral angle of 55.2 (1)°. The β-lactam ring is planar, with a maximum deviation of −0.109 (1)° for atom O1.

The molecular structure is influenced by a π–π interaction between the five-membered ring (C21/C22/N3/C23/C28) of one indole moiety and the phenyl ring (C30–C35), with a centroid separation of 3.695 (1) Å (Fig. 2). In the crystal structure, the molecules are linked by N—H···O1 hydrogen bonds so that a helical structure is formed. In addition, inversion-related molecules are linked by weak N—H···π interactions: H3 is 2.53 Å from the centroid of the five-membered ring composed of atoms C12/C13/N2/C14/C19 at (1 − x,-y,1 − z), with an N3—H3···centroid angle of 152° and an N3···centroid distance of 3.317 (1) Å.

S2. Experimental

A mixture of 2-methylindole (2.5 mmol), 4-formylazetidinone (1.25 mmol) and gadolinium trifluoromethanesulfonate (55 mg, 0.093 mmol) was stirred in acetonitrile (6 ml). After completion of the reaction, water was added to quench the reaction and the product was extracted with ethyl acetate (3 × 10 ml) and washed with an aqueous sodium bicarbonate and sodium chloride solution; the combined organic layers were dried using anhydrous Na₂SO₄ and filtered. The solvent was then evaporated. The crude product was purified by column chromatography and eluted with an ethyl acetate and hexane (3:1 (v/v) mixture to afford the title compound. To obtain diffraction quality crystals, recrystallization was carried out from an ethyl acetate–hexane (1:1 (v/v) mixture.

S3. Refinement

The H atoms were positioned geometrically and were treated as riding on their parent atoms, with C—H distances of 0.93–0.98 Å, N—H distances of 0.86 Å and with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C or N) for the other H atoms. Methyl atom C29 was allowed to rotate but not to tip.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the molecular packing of (I), showing N—H···O, N—H···π and π–π interactions as dashed lines. For the sake of clarity, H atoms not involved in hydrogen bonds have been omitted.

4-[Bis(2-methyl-1H-indol-3-yl)methyl]-1-(4-methoxyphenyl)-3-phenylazetidin- 2-one

Crystal data

C35H31N3O2	F(000) = 1112
Mr = 525.63	Dx = 1.257 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11212 reflections
a = 11.9751 (7) Å	θ = 2.2–23.4°
b = 13.4815 (8) Å	µ = 0.08 mm^−1
c = 17.2114 (11) Å	T = 293 K
β = 91.978 (1)°	Block, colourless
V = 2777.0 (3) Å^3	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection

CCD area-detector diffractometer	5325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 28.0°, θmin = 1.9°
ω scans	h = −15→15
31001 measured reflections	k = −17→17
6519 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.08P)^2 + 0.5932P] where P = (Fo^2 + 2Fc^2)/3
6519 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.59029 (9)	0.23703 (8)	0.11658 (6)	0.0554 (3)
O2	0.68659 (10)	−0.21135 (9)	−0.03740 (7)	0.0632 (3)
N1	0.54200 (10)	0.07997 (9)	0.16433 (6)	0.0429 (3)
N2	0.71139 (11)	−0.15471 (11)	0.33046 (8)	0.0584 (3)
H2	0.7783	−0.1776	0.3354	0.070*
N3	0.36215 (11)	0.11854 (9)	0.48359 (7)	0.0509 (3)
H3	0.3620	0.1420	0.5300	0.061*
C1	0.45976 (11)	0.07649 (10)	0.22669 (7)	0.0392 (3)
H1	0.3931	0.0375	0.2124	0.047*
C2	0.44312 (11)	0.19115 (10)	0.21277 (8)	0.0435 (3)
H2A	0.3727	0.2020	0.1832	0.052*
C3	0.53734 (11)	0.18046 (10)	0.15643 (7)	0.0435 (3)
C4	0.58073 (11)	0.00436 (11)	0.11538 (7)	0.0432 (3)
C5	0.54765 (14)	−0.09251 (11)	0.12555 (8)	0.0528 (4)
H5	0.5024	−0.1083	0.1666	0.063*
C6	0.58059 (14)	−0.16690 (12)	0.07578 (8)	0.0543 (4)
H6	0.5572	−0.2319	0.0833	0.065*
C7	0.64828 (12)	−0.14412 (12)	0.01494 (8)	0.0486 (3)
C8	0.68095 (14)	−0.04706 (13)	0.00443 (9)	0.0559 (4)
H8	0.7261	−0.0316	−0.0368	0.067*
C9	0.64835 (13)	0.02742 (12)	0.05349 (8)	0.0511 (3)
H9	0.6712	0.0924	0.0454	0.061*
C10	0.65488 (16)	−0.31203 (13)	−0.02868 (10)	0.0618 (4)
H10A	0.6871	−0.3511	−0.0688	0.093*
H10B	0.5749	−0.3173	−0.0326	0.093*
H10C	0.6812	−0.3358	0.0212	0.093*
C11	0.50927 (10)	0.05056 (9)	0.30724 (7)	0.0372 (3)
H11	0.5671	0.1008	0.3176	0.045*
C12	0.56971 (11)	−0.04732 (10)	0.31413 (7)	0.0398 (3)
C13	0.68380 (12)	−0.05656 (12)	0.31915 (8)	0.0498 (3)
C14	0.61568 (13)	−0.21048 (11)	0.33260 (8)	0.0497 (3)
C15	0.60232 (17)	−0.31206 (13)	0.34411 (10)	0.0660 (5)
H15	0.6636	−0.3537	0.3520	0.079*
C16	0.49572 (19)	−0.34809 (13)	0.34338 (12)	0.0736 (5)
H16	0.4843	−0.4157	0.3504	0.088*
C17	0.40370 (16)	−0.28600 (13)	0.33237 (11)	0.0655 (4)
H17	0.3322	−0.3129	0.3324	0.079*
C18	0.41653 (13)	−0.18540 (11)	0.32138 (9)	0.0497 (3)
H18	0.3544	−0.1447	0.3136	0.060*
C19	0.52436 (11)	−0.14537 (10)	0.32206 (7)	0.0410 (3)
C20	0.77400 (14)	0.01888 (17)	0.31435 (13)	0.0749 (5)
H20A	0.8454	−0.0130	0.3208	0.112*
H20B	0.7659	0.0673	0.3546	0.112*
H20C	0.7689	0.0510	0.2646	0.112*
C21	0.42471 (11)	0.06678 (9)	0.36965 (7)	0.0366 (3)
C22	0.45547 (12)	0.10554 (10)	0.44083 (8)	0.0429 (3)
C23	0.26937 (12)	0.08868 (11)	0.44159 (8)	0.0471 (3)
C24	0.15778 (15)	0.08975 (14)	0.46154 (10)	0.0624 (4)
H24	0.1367	0.1130	0.5097	0.075*
C25	0.07993 (14)	0.05536 (15)	0.40781 (11)	0.0672 (5)
H25	0.0048	0.0549	0.4198	0.081*
C26	0.11188 (13)	0.02097 (14)	0.33533 (10)	0.0590 (4)
H26	0.0576	−0.0023	0.2999	0.071*
C27	0.22223 (12)	0.02095 (11)	0.31529 (8)	0.0462 (3)
H27	0.2418	−0.0017	0.2666	0.055*
C28	0.30526 (11)	0.05503 (9)	0.36841 (7)	0.0392 (3)
C29	0.56762 (14)	0.13309 (12)	0.47331 (9)	0.0550 (4)
H29A	0.5955	0.0809	0.5066	0.082*
H29B	0.5622	0.1933	0.5027	0.082*
H29C	0.6177	0.1428	0.4316	0.082*
C30	0.45151 (15)	0.26413 (10)	0.27847 (9)	0.0537 (4)
C31	0.3540 (2)	0.29040 (13)	0.31582 (11)	0.0742 (5)
H31	0.2854	0.2663	0.2973	0.089*
C32	0.3587 (3)	0.35138 (18)	0.37954 (15)	0.1077 (10)
H32	0.2936	0.3672	0.4046	0.129*
C33	0.4580 (4)	0.38870 (18)	0.40616 (15)	0.1189 (12)
H33	0.4604	0.4294	0.4498	0.143*
C34	0.5571 (3)	0.36657 (16)	0.36862 (15)	0.1045 (10)
H34	0.6248	0.3937	0.3862	0.125*
C35	0.5523 (2)	0.30309 (13)	0.30442 (11)	0.0711 (5)
H35	0.6173	0.2871	0.2792	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0586 (6)	0.0538 (6)	0.0539 (6)	−0.0159 (5)	0.0054 (5)	0.0109 (5)
O2	0.0743 (8)	0.0664 (7)	0.0499 (6)	−0.0029 (6)	0.0176 (5)	−0.0118 (5)
N1	0.0491 (6)	0.0456 (6)	0.0346 (5)	−0.0074 (5)	0.0076 (4)	0.0017 (4)
N2	0.0457 (7)	0.0695 (9)	0.0599 (8)	0.0184 (6)	0.0030 (6)	−0.0039 (6)
N3	0.0646 (8)	0.0544 (7)	0.0339 (5)	0.0040 (6)	0.0066 (5)	−0.0075 (5)
C1	0.0410 (6)	0.0433 (7)	0.0334 (6)	−0.0056 (5)	0.0042 (5)	0.0001 (5)
C2	0.0452 (7)	0.0460 (7)	0.0390 (6)	−0.0002 (5)	−0.0013 (5)	0.0056 (5)
C3	0.0451 (7)	0.0476 (7)	0.0374 (6)	−0.0077 (5)	−0.0033 (5)	0.0037 (5)
C4	0.0463 (7)	0.0508 (7)	0.0326 (6)	−0.0051 (6)	0.0028 (5)	−0.0012 (5)
C5	0.0666 (9)	0.0529 (8)	0.0398 (7)	−0.0098 (7)	0.0159 (6)	−0.0005 (6)
C6	0.0719 (10)	0.0493 (8)	0.0422 (7)	−0.0085 (7)	0.0112 (7)	−0.0018 (6)
C7	0.0513 (8)	0.0587 (8)	0.0360 (6)	−0.0017 (6)	0.0033 (5)	−0.0049 (6)
C8	0.0604 (9)	0.0660 (10)	0.0424 (7)	−0.0109 (7)	0.0175 (6)	−0.0015 (7)
C9	0.0558 (8)	0.0548 (8)	0.0433 (7)	−0.0134 (6)	0.0112 (6)	0.0009 (6)
C10	0.0690 (10)	0.0583 (9)	0.0581 (9)	0.0105 (8)	0.0022 (8)	−0.0078 (7)
C11	0.0396 (6)	0.0382 (6)	0.0339 (6)	−0.0028 (5)	0.0026 (5)	−0.0001 (5)
C12	0.0412 (6)	0.0451 (7)	0.0333 (6)	0.0023 (5)	0.0045 (5)	−0.0011 (5)
C13	0.0434 (7)	0.0618 (9)	0.0444 (7)	0.0045 (6)	0.0058 (6)	−0.0020 (6)
C14	0.0560 (8)	0.0530 (8)	0.0401 (7)	0.0144 (6)	0.0027 (6)	−0.0047 (6)
C15	0.0852 (12)	0.0510 (9)	0.0614 (10)	0.0248 (8)	−0.0036 (9)	−0.0035 (7)
C16	0.1003 (15)	0.0410 (8)	0.0791 (12)	0.0051 (9)	−0.0032 (10)	0.0009 (8)
C17	0.0719 (11)	0.0490 (9)	0.0757 (11)	−0.0075 (8)	0.0027 (9)	−0.0020 (8)
C18	0.0515 (8)	0.0434 (7)	0.0541 (8)	0.0012 (6)	0.0027 (6)	−0.0020 (6)
C19	0.0491 (7)	0.0421 (7)	0.0320 (6)	0.0068 (5)	0.0044 (5)	−0.0018 (5)
C20	0.0434 (8)	0.0929 (14)	0.0890 (13)	−0.0078 (9)	0.0096 (8)	0.0001 (11)
C21	0.0434 (6)	0.0340 (6)	0.0325 (6)	0.0017 (5)	0.0021 (5)	0.0018 (4)
C22	0.0537 (7)	0.0398 (6)	0.0352 (6)	0.0014 (5)	0.0011 (5)	0.0013 (5)
C23	0.0544 (8)	0.0449 (7)	0.0424 (7)	0.0066 (6)	0.0088 (6)	−0.0005 (5)
C24	0.0619 (9)	0.0698 (10)	0.0566 (9)	0.0108 (8)	0.0199 (8)	−0.0047 (8)
C25	0.0451 (8)	0.0845 (12)	0.0728 (11)	0.0091 (8)	0.0161 (8)	0.0003 (9)
C26	0.0449 (8)	0.0701 (10)	0.0620 (9)	0.0010 (7)	−0.0005 (7)	0.0032 (8)
C27	0.0455 (7)	0.0510 (8)	0.0420 (7)	0.0022 (6)	0.0029 (5)	0.0011 (6)
C28	0.0448 (7)	0.0357 (6)	0.0374 (6)	0.0052 (5)	0.0050 (5)	0.0026 (5)
C29	0.0645 (9)	0.0580 (9)	0.0418 (7)	−0.0074 (7)	−0.0082 (6)	−0.0011 (6)
C30	0.0800 (11)	0.0371 (7)	0.0439 (7)	0.0055 (7)	0.0008 (7)	0.0069 (6)
C31	0.1076 (15)	0.0491 (9)	0.0669 (11)	0.0260 (9)	0.0176 (10)	0.0048 (8)
C32	0.185 (3)	0.0570 (12)	0.0825 (16)	0.0354 (16)	0.0302 (18)	−0.0079 (11)
C33	0.238 (4)	0.0519 (12)	0.0673 (14)	0.0141 (18)	0.010 (2)	−0.0150 (10)
C34	0.181 (3)	0.0516 (11)	0.0785 (15)	−0.0239 (14)	−0.0380 (17)	0.0029 (10)
C35	0.1068 (15)	0.0486 (9)	0.0566 (9)	−0.0134 (9)	−0.0135 (9)	0.0042 (7)

Geometric parameters (Å, º)

O1—C3	1.218 (2)	C15—C16	1.366 (3)
O2—C7	1.3681 (18)	C15—H15	0.9300
O2—C10	1.419 (2)	C16—C17	1.391 (3)
N1—C3	1.363 (2)	C16—H16	0.9300
N1—C4	1.411 (2)	C17—C18	1.379 (2)
N1—C1	1.482 (2)	C17—H17	0.9300
N2—C14	1.372 (2)	C18—C19	1.399 (2)
N2—C13	1.376 (2)	C18—H18	0.9300
N2—H2	0.8600	C20—H20A	0.9600
N3—C23	1.365 (2)	C20—H20B	0.9600
N3—C22	1.371 (2)	C20—H20C	0.9600
N3—H3	0.8600	C21—C22	1.3706 (18)
C1—C11	1.5293 (17)	C21—C28	1.4387 (18)
C1—C2	1.5758 (18)	C22—C29	1.484 (2)
C1—H1	0.9800	C23—C24	1.391 (2)
C2—C30	1.500 (2)	C23—C28	1.4192 (18)
C2—C3	1.5197 (19)	C24—C25	1.371 (3)
C2—H2A	0.9800	C24—H24	0.9300
C4—C5	1.378 (2)	C25—C26	1.397 (3)
C4—C9	1.3951 (18)	C25—H25	0.9300
C5—C6	1.385 (2)	C26—C27	1.377 (2)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.381 (2)	C27—C28	1.404 (2)
C6—H6	0.9300	C27—H27	0.9300
C7—C8	1.379 (2)	C29—H29A	0.9600
C8—C9	1.377 (2)	C29—H29B	0.9600
C8—H8	0.9300	C29—H29C	0.9600
C9—H9	0.9300	C30—C35	1.376 (3)
C10—H10A	0.9600	C30—C31	1.398 (3)
C10—H10B	0.9600	C31—C32	1.370 (3)
C10—H10C	0.9600	C31—H31	0.9300
C11—C12	1.5078 (18)	C32—C33	1.356 (5)
C11—C21	1.5172 (17)	C32—H32	0.9300
C11—H11	0.9800	C33—C34	1.403 (5)
C12—C13	1.372 (2)	C33—H33	0.9300
C12—C19	1.4373 (19)	C34—C35	1.397 (3)
C13—C20	1.488 (2)	C34—H34	0.9300
C14—C15	1.394 (2)	C35—H35	0.9300
C14—C19	1.4091 (19)
C7—O2—C10	117.85 (12)	C15—C16—C17	121.53 (16)
C3—N1—C4	132.2 (1)	C15—C16—H16	119.2
C3—N1—C1	94.5 (1)	C17—C16—H16	119.2
C4—N1—C1	130.5 (1)	C18—C17—C16	121.26 (17)
C14—N2—C13	109.51 (12)	C18—C17—H17	119.4
C14—N2—H2	125.2	C16—C17—H17	119.4
C13—N2—H2	125.2	C17—C18—C19	119.04 (14)
C23—N3—C22	109.99 (11)	C17—C18—H18	120.5
C23—N3—H3	125.0	C19—C18—H18	120.5
C22—N3—H3	125.0	C18—C19—C14	118.21 (13)
N1—C1—C11	114.66 (11)	C18—C19—C12	134.87 (12)
N1—C1—C2	86.71 (9)	C14—C19—C12	106.92 (12)
C11—C1—C2	113.90 (10)	C13—C20—H20A	109.5
N1—C1—H1	113.0	C13—C20—H20B	109.5
C11—C1—H1	113.0	H20A—C20—H20B	109.5
C2—C1—H1	113.0	C13—C20—H20C	109.5
C30—C2—C3	120.76 (12)	H20A—C20—H20C	109.5
C30—C2—C1	121.61 (11)	H20B—C20—H20C	109.5
C3—C2—C1	84.91 (10)	C22—C21—C28	106.96 (11)
C30—C2—H2A	109.1	C22—C21—C11	121.50 (12)
C3—C2—H2A	109.1	C28—C21—C11	131.39 (11)
C1—C2—H2A	109.1	N3—C22—C21	109.26 (12)
O1—C3—N1	131.17 (14)	N3—C22—C29	120.66 (13)
O1—C3—C2	135.41 (14)	C21—C22—C29	130.09 (13)
N1—C3—C2	93.41 (10)	N3—C23—C24	129.60 (14)
C5—C4—C9	119.03 (13)	N3—C23—C28	107.36 (12)
C5—C4—N1	120.46 (12)	C24—C23—C28	123.03 (15)
C9—C4—N1	120.42 (13)	C25—C24—C23	117.82 (15)
C4—C5—C6	121.23 (13)	C25—C24—H24	121.1
C4—C5—H5	119.4	C23—C24—H24	121.1
C6—C5—H5	119.4	C24—C25—C26	120.92 (15)
C7—C6—C5	119.68 (14)	C24—C25—H25	119.5
C7—C6—H6	120.2	C26—C25—H25	119.5
C5—C6—H6	120.2	C27—C26—C25	121.23 (16)
O2—C7—C8	116.0 (1)	C27—C26—H26	119.4
O2—C7—C6	124.8 (1)	C25—C26—H26	119.4
C8—C7—C6	119.14 (13)	C26—C27—C28	120.05 (14)
C9—C8—C7	121.57 (13)	C26—C27—H27	120.0
C9—C8—H8	119.2	C28—C27—H27	120.0
C7—C8—H8	119.2	C27—C28—C23	116.94 (12)
C8—C9—C4	119.34 (14)	C27—C28—C21	136.62 (12)
C8—C9—H9	120.3	C23—C28—C21	106.44 (12)
C4—C9—H9	120.3	C22—C29—H29A	109.5
O2—C10—H10A	109.5	C22—C29—H29B	109.5
O2—C10—H10B	109.5	H29A—C29—H29B	109.5
H10A—C10—H10B	109.5	C22—C29—H29C	109.5
O2—C10—H10C	109.5	H29A—C29—H29C	109.5
H10A—C10—H10C	109.5	H29B—C29—H29C	109.5
H10B—C10—H10C	109.5	C35—C30—C31	119.41 (18)
C12—C11—C21	113.6 (1)	C35—C30—C2	122.02 (16)
C12—C11—C1	116.2 (1)	C31—C30—C2	118.53 (16)
C21—C11—C1	111.2 (1)	C32—C31—C30	120.5 (3)
C12—C11—H11	104.8	C32—C31—H31	119.7
C21—C11—H11	104.8	C30—C31—H31	119.7
C1—C11—H11	104.8	C33—C32—C31	120.3 (3)
C13—C12—C19	106.82 (12)	C33—C32—H32	119.8
C13—C12—C11	123.97 (12)	C31—C32—H32	119.8
C19—C12—C11	129.09 (11)	C32—C33—C34	120.7 (2)
C12—C13—N2	109.27 (13)	C32—C33—H33	119.6
C12—C13—C20	131.14 (15)	C34—C33—H33	119.6
N2—C13—C20	119.60 (14)	C35—C34—C33	118.8 (3)
N2—C14—C15	129.96 (15)	C35—C34—H34	120.6
N2—C14—C19	107.48 (13)	C33—C34—H34	120.6
C15—C14—C19	122.55 (15)	C30—C35—C34	120.1 (2)
C16—C15—C14	117.39 (16)	C30—C35—H35	119.9
C16—C15—H15	121.3	C34—C35—H35	119.9
C14—C15—H15	121.3
C3—N1—C1—C11	−109.24 (12)	C15—C16—C17—C18	0.3 (3)
C4—N1—C1—C11	88.33 (16)	C16—C17—C18—C19	−0.6 (3)
C3—N1—C1—C2	5.60 (10)	C17—C18—C19—C14	1.2 (2)
C4—N1—C1—C2	−156.83 (14)	C17—C18—C19—C12	−178.88 (15)
N1—C1—C2—C30	−128.26 (14)	N2—C14—C19—C18	179.47 (12)
C11—C1—C2—C30	−12.69 (18)	C15—C14—C19—C18	−1.6 (2)
N1—C1—C2—C3	−5.02 (9)	N2—C14—C19—C12	−0.51 (15)
C11—C1—C2—C3	110.54 (11)	C15—C14—C19—C12	178.48 (14)
C4—N1—C3—O1	−22.7 (3)	C13—C12—C19—C18	−179.32 (15)
C1—N1—C3—O1	175.37 (15)	C11—C12—C19—C18	4.7 (2)
C4—N1—C3—C2	156.14 (14)	C13—C12—C19—C14	0.65 (14)
C1—N1—C3—C2	−5.81 (10)	C11—C12—C19—C14	−175.30 (12)
C30—C2—C3—O1	−51.8 (2)	C12—C11—C21—C22	85.63 (15)
C1—C2—C3—O1	−175.80 (16)	C1—C11—C21—C22	−141.03 (12)
C30—C2—C3—N1	129.47 (13)	C12—C11—C21—C28	−99.56 (15)
C1—C2—C3—N1	5.47 (10)	C1—C11—C21—C28	33.78 (18)
C3—N1—C4—C5	−161.00 (15)	C23—N3—C22—C21	0.07 (16)
C1—N1—C4—C5	−5.0 (2)	C23—N3—C22—C29	179.60 (13)
C3—N1—C4—C9	15.6 (2)	C28—C21—C22—N3	−0.07 (15)
C1—N1—C4—C9	171.65 (13)	C11—C21—C22—N3	175.86 (11)
C9—C4—C5—C6	0.2 (2)	C28—C21—C22—C29	−179.54 (14)
N1—C4—C5—C6	176.91 (14)	C11—C21—C22—C29	−3.6 (2)
C4—C5—C6—C7	0.3 (3)	C22—N3—C23—C24	−179.13 (16)
C10—O2—C7—C8	−180.0 (2)	C22—N3—C23—C28	−0.04 (16)
C10—O2—C7—C6	−0.1 (2)	N3—C23—C24—C25	179.78 (17)
C5—C6—C7—O2	179.51 (15)	C28—C23—C24—C25	0.8 (3)
C5—C6—C7—C8	−0.7 (2)	C23—C24—C25—C26	−0.4 (3)
O2—C7—C8—C9	−179.67 (15)	C24—C25—C26—C27	−0.4 (3)
C6—C7—C8—C9	0.5 (2)	C25—C26—C27—C28	0.6 (2)
C7—C8—C9—C4	0.0 (3)	C26—C27—C28—C23	−0.2 (2)
C5—C4—C9—C8	−0.4 (2)	C26—C27—C28—C21	−179.77 (15)
N1—C4—C9—C8	−177.09 (14)	N3—C23—C28—C27	−179.72 (12)
N1—C1—C11—C12	−58.29 (15)	C24—C23—C28—C27	−0.6 (2)
C2—C1—C11—C12	−156.0 (1)	N3—C23—C28—C21	0.00 (15)
N1—C1—C11—C21	169.66 (10)	C24—C23—C28—C21	179.16 (14)
C2—C1—C11—C21	72.0 (1)	C22—C21—C28—C27	179.68 (15)
C21—C11—C12—C13	−124.66 (14)	C11—C21—C28—C27	4.3 (2)
C1—C11—C12—C13	104.42 (15)	C22—C21—C28—C23	0.04 (14)
C21—C11—C12—C19	50.66 (17)	C11—C21—C28—C23	−175.32 (12)
C1—C11—C12—C19	−80.25 (16)	C3—C2—C30—C35	−18.8 (2)
C19—C12—C13—N2	−0.55 (15)	C1—C2—C30—C35	85.41 (18)
C11—C12—C13—N2	175.66 (12)	C3—C2—C30—C31	163.41 (13)
C19—C12—C13—C20	179.39 (17)	C1—C2—C30—C31	−92.41 (17)
C11—C12—C13—C20	−4.4 (3)	C35—C30—C31—C32	−2.5 (3)
C14—N2—C13—C12	0.24 (17)	C2—C30—C31—C32	175.42 (17)
C14—N2—C13—C20	−179.71 (15)	C30—C31—C32—C33	1.4 (3)
C13—N2—C14—C15	−178.70 (16)	C31—C32—C33—C34	0.7 (4)
C13—N2—C14—C19	0.18 (16)	C32—C33—C34—C35	−1.7 (4)
N2—C14—C15—C16	−179.99 (17)	C31—C30—C35—C34	1.4 (2)
C19—C14—C15—C16	1.3 (2)	C2—C30—C35—C34	−176.39 (16)
C14—C15—C16—C17	−0.6 (3)	C33—C34—C35—C30	0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	2.10	2.907 (2)	157

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.