Methyl 3-(4-bromo-phen-yl)-2-(1H-indol-3-ylmeth-yl)-5-[1-(4-methoxy-phen-yl)-4-oxo-2-phenyl-azetidin-2-yl]-4-nitro-pyrrolidine-2-carboxyl-ate.

In the title compound, C(37)H(33)BrN(4)O(6), the pyrrolidine ring adopts an envelope conformation. The β-lactam ring is planar and makes dihedral angles of 70.16 (13) and 28.32 (13)° with the phenyl and 4-methoxy-phenyl rings, respectively. The mol-ecular packing is stabilized by intra-molecular C-H⋯O inter-actions and the crystal packing is determined by inter-molecular N-H⋯O hydrogen bonds, and C-H⋯O and C-H⋯π inter-actions.

Related literature

For related literature, see: Kamala et al. (2008 ▶); Lukacs & Ohno (1990 ▶); Sundari Bhaskaran et al. (2006 ▶); Suzuki et al. (1994 ▶); Yang et al. (1987 ▶); Amal Raj et al. (2003 ▶); Cremer & Pople (1975 ▶); Nardelli (1995 ▶); Ülkü et al. (1997 ▶).

Experimental

Crystal data

C37H33BrN4O6

M = 709.58

Monoclinic,

a = 11.3988 (4) Å

b = 34.8587 (13) Å

c = 8.7039 (3) Å

β = 100.982 (2)°

V = 3395.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 293 (2) K

0.30 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.703, T max = 0.769

37282 measured reflections

8532 independent reflections

6397 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.04

8532 reflections

433 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 4142 Friedel pairs

Flack parameter: 0.008 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014190/rk2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014190/rk2086Isup2.hkl

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

C37H33BrN4O6	F000 = 1464
Mr = 709.58	Dx = 1.388 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 13968 reflections
a = 11.3988 (4) Å	θ = 2.3–23.4º
b = 34.8587 (13) Å	µ = 1.26 mm−1
c = 8.7039 (3) Å	T = 293 (2) K
β = 100.982 (2)º	Prism, colourless
V = 3395.1 (2) Å3	0.30 × 0.22 × 0.22 mm
Z = 4

Bruker Kappa APEX2 diffractometer	8532 independent reflections
Radiation source: fine–focus sealed tube	6397 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 293(2) K	θmax = 28.7º
ω and φ scans	θmin = 1.2º
Absorption correction: multi-scan(Blessing, 1995)	h = −15→15
Tmin = 0.703, Tmax = 0.769	k = −46→46
37282 measured reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0682P)2 + 0.1826P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max = 0.002
S = 1.04	Δρmax = 0.43 e Å−3
8532 reflections	Δρmin = −0.37 e Å−3
433 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 4142 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.008 (6)
Secondary atom site location: difference Fourier map

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	1.0310 (3)	0.82854 (8)	0.0512 (3)	0.0541 (6)
H1	0.9961	0.8156	0.1244	0.065*
C2	0.9937 (2)	0.86265 (6)	−0.0140 (3)	0.0406 (5)
C3	1.07094 (19)	0.87204 (7)	−0.1184 (3)	0.0388 (5)
C4	1.0793 (2)	0.90284 (8)	−0.2186 (3)	0.0490 (6)
H4	1.0255	0.9231	−0.2262	0.059*
C5	1.1678 (3)	0.90276 (10)	−0.3055 (4)	0.0609 (7)
H5	1.1734	0.9231	−0.3728	0.073*
C6	1.2498 (3)	0.87257 (11)	−0.2947 (4)	0.0628 (8)
H6	1.3096	0.8734	−0.3539	0.075*
C7	1.2437 (2)	0.84207 (9)	−0.1991 (4)	0.0594 (7)
H7	1.2978	0.8219	−0.1932	0.071*
C8	1.1543 (2)	0.84186 (7)	−0.1104 (3)	0.0446 (5)
C9	0.8907 (2)	0.88613 (7)	0.0180 (3)	0.0405 (5)
H9A	0.8213	0.8697	0.0119	0.049*
H9B	0.8715	0.9057	−0.0622	0.049*
C10	0.91742 (18)	0.90557 (6)	0.1798 (2)	0.0352 (5)
C11	0.81174 (18)	0.93273 (6)	0.2125 (3)	0.0349 (4)
H11	0.8474	0.9573	0.2510	0.042*
C12	0.7686 (2)	0.91299 (6)	0.3488 (3)	0.0386 (5)
H12	0.6811	0.9128	0.3319	0.046*
C13	0.8177 (2)	0.87176 (6)	0.3464 (3)	0.0385 (5)
H13	0.7664	0.8584	0.2596	0.046*
C14	0.8218 (2)	0.84705 (7)	0.4896 (3)	0.0435 (5)
H14	0.8738	0.8578	0.5822	0.052*
C15	0.6981 (3)	0.83327 (8)	0.5252 (3)	0.0538 (6)
H15	0.6945	0.8369	0.6359	0.065*
C16	0.7435 (3)	0.79315 (9)	0.4961 (4)	0.0637 (8)
C17	0.9507 (3)	0.78706 (8)	0.4405 (3)	0.0561 (7)
C18	1.0634 (3)	0.80218 (9)	0.4846 (4)	0.0689 (9)
H18	1.0722	0.8259	0.5342	0.083*
C19	1.1637 (4)	0.78329 (10)	0.4579 (5)	0.0771 (10)
H19	1.2383	0.7949	0.4852	0.093*
C20	1.1543 (4)	0.74769 (10)	0.3916 (5)	0.0737 (9)
C21	1.0396 (5)	0.73262 (11)	0.3432 (6)	0.0990 (15)
H21	1.0312	0.7087	0.2950	0.119*
C22	0.9395 (4)	0.75174 (10)	0.3643 (6)	0.0893 (13)
H22	0.8642	0.7413	0.3281	0.107*
C23	1.3582 (4)	0.74477 (16)	0.3661 (7)	0.1051 (14)
H23A	1.4164	0.7267	0.3445	0.158*
H23B	1.3853	0.7559	0.4674	0.158*
H23C	1.3475	0.7646	0.2881	0.158*
C24	0.5431 (3)	0.82771 (10)	0.2772 (4)	0.0665 (8)
H24	0.5881	0.8082	0.2445	0.080*
C25	0.4380 (3)	0.83898 (13)	0.1818 (4)	0.0798 (10)
H25	0.4118	0.8263	0.0876	0.096*
C26	0.3718 (3)	0.86851 (12)	0.2234 (5)	0.0801 (10)
H26	0.3024	0.8766	0.1571	0.096*
C27	0.4099 (3)	0.88592 (13)	0.3652 (5)	0.0802 (10)
H27	0.3645	0.9057	0.3958	0.096*
C28	0.5143 (3)	0.87489 (11)	0.4641 (4)	0.0685 (8)
H28	0.5386	0.8874	0.5591	0.082*
C29	0.5832 (3)	0.84510 (8)	0.4218 (3)	0.0544 (6)
C30	0.71391 (19)	0.94108 (6)	0.0732 (3)	0.0363 (4)
C31	0.7291 (2)	0.97173 (7)	−0.0228 (3)	0.0465 (6)
H31	0.7989	0.9862	−0.0002	0.056*
C32	0.6435 (2)	0.98119 (8)	−0.1500 (4)	0.0544 (7)
H32	0.6561	1.0016	−0.2139	0.065*
C33	0.5397 (2)	0.96064 (8)	−0.1828 (3)	0.0508 (6)
C34	0.5213 (2)	0.93019 (9)	−0.0920 (4)	0.0586 (7)
H34	0.4507	0.9161	−0.1153	0.070*
C35	0.6090 (2)	0.92037 (8)	0.0358 (3)	0.0498 (6)
H35	0.5969	0.8995	0.0973	0.060*
C36	1.0328 (2)	0.92886 (7)	0.1965 (3)	0.0419 (5)
C37	1.1292 (3)	0.97884 (10)	0.0855 (6)	0.0814 (11)
H37A	1.1137	0.9966	−0.0002	0.122*
H37B	1.1957	0.9628	0.0749	0.122*
H37C	1.1476	0.9927	0.1823	0.122*
N1	1.1279 (2)	0.81582 (6)	−0.0061 (3)	0.0549 (5)
H1A	1.1659	0.7948	0.0197	0.066*
N2	0.93345 (17)	0.87641 (5)	0.3021 (2)	0.0397 (4)
H2	0.9983	0.8644	0.3403	0.048*
N3	0.8208 (2)	0.93141 (6)	0.5030 (3)	0.0462 (5)
N4	0.8479 (2)	0.80657 (6)	0.4657 (3)	0.0533 (5)
O1	1.11802 (17)	0.92443 (7)	0.2958 (3)	0.0690 (6)
O2	1.02387 (15)	0.95506 (5)	0.0846 (2)	0.0551 (4)
O3	0.7714 (2)	0.92499 (8)	0.6116 (3)	0.0771 (7)
O4	0.91172 (19)	0.95038 (6)	0.5130 (2)	0.0617 (5)
O5	0.7038 (3)	0.76121 (7)	0.4957 (4)	0.0892 (8)
O6	1.2477 (3)	0.72571 (8)	0.3636 (4)	0.0996 (10)
Br1	0.42238 (4)	0.974927 (13)	−0.35828 (4)	0.08931 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0691 (16)	0.0355 (13)	0.0601 (16)	0.0073 (11)	0.0179 (13)	0.0020 (11)
C2	0.0465 (11)	0.0341 (12)	0.0418 (12)	0.0011 (9)	0.0097 (9)	−0.0032 (10)
C3	0.0393 (10)	0.0357 (12)	0.0389 (12)	0.0034 (9)	0.0016 (9)	−0.0057 (9)
C4	0.0522 (12)	0.0504 (15)	0.0435 (14)	0.0073 (11)	0.0067 (11)	0.0041 (11)
C5	0.0677 (17)	0.0685 (18)	0.0483 (15)	−0.0068 (14)	0.0159 (13)	0.0043 (14)
C6	0.0496 (14)	0.089 (2)	0.0536 (16)	−0.0031 (14)	0.0189 (12)	−0.0149 (16)
C7	0.0468 (13)	0.0708 (19)	0.0589 (17)	0.0136 (12)	0.0055 (12)	−0.0192 (15)
C8	0.0451 (12)	0.0426 (13)	0.0427 (13)	0.0089 (9)	0.0000 (10)	−0.0086 (11)
C9	0.0417 (11)	0.0359 (12)	0.0437 (12)	0.0013 (9)	0.0078 (9)	0.0000 (9)
C10	0.0327 (8)	0.0302 (10)	0.0436 (13)	0.0009 (8)	0.0094 (9)	0.0040 (9)
C11	0.0365 (10)	0.0263 (10)	0.0431 (12)	−0.0011 (8)	0.0103 (8)	0.0000 (9)
C12	0.0389 (10)	0.0354 (11)	0.0419 (12)	−0.0018 (8)	0.0085 (9)	0.0004 (9)
C13	0.0467 (11)	0.0272 (10)	0.0407 (11)	−0.0055 (9)	0.0060 (9)	−0.0010 (9)
C14	0.0566 (13)	0.0337 (12)	0.0378 (11)	−0.0081 (10)	0.0027 (10)	0.0031 (9)
C15	0.0735 (17)	0.0474 (15)	0.0435 (14)	−0.0171 (12)	0.0186 (12)	0.0037 (11)
C16	0.090 (2)	0.0456 (16)	0.0543 (16)	−0.0199 (14)	0.0108 (15)	0.0120 (13)
C17	0.0870 (19)	0.0333 (13)	0.0462 (14)	−0.0035 (12)	0.0080 (13)	0.0045 (11)
C18	0.0743 (19)	0.0456 (16)	0.073 (2)	0.0130 (14)	−0.0217 (15)	−0.0056 (14)
C19	0.079 (2)	0.0572 (19)	0.082 (2)	0.0090 (16)	−0.0163 (17)	0.0014 (17)
C20	0.104 (3)	0.0501 (17)	0.0684 (19)	0.0108 (17)	0.0196 (18)	0.0024 (15)
C21	0.138 (4)	0.0461 (18)	0.128 (4)	−0.017 (2)	0.064 (3)	−0.032 (2)
C22	0.107 (3)	0.0497 (18)	0.122 (3)	−0.0272 (19)	0.050 (3)	−0.026 (2)
C23	0.089 (3)	0.113 (4)	0.105 (3)	0.030 (3)	−0.003 (2)	0.004 (3)
C24	0.0708 (18)	0.0644 (19)	0.0642 (19)	−0.0175 (15)	0.0123 (15)	−0.0084 (15)
C25	0.071 (2)	0.097 (3)	0.065 (2)	−0.0285 (19)	−0.0031 (17)	−0.0118 (18)
C26	0.0577 (17)	0.100 (3)	0.081 (2)	−0.0084 (18)	0.0086 (16)	0.001 (2)
C27	0.0580 (18)	0.105 (3)	0.081 (2)	−0.0011 (17)	0.0217 (17)	−0.003 (2)
C28	0.0642 (18)	0.089 (2)	0.0569 (17)	−0.0115 (16)	0.0242 (14)	−0.0088 (16)
C29	0.0562 (14)	0.0562 (16)	0.0527 (15)	−0.0229 (12)	0.0150 (12)	0.0019 (12)
C30	0.0364 (10)	0.0284 (10)	0.0459 (12)	0.0033 (8)	0.0127 (9)	0.0020 (9)
C31	0.0422 (11)	0.0388 (13)	0.0579 (15)	−0.0039 (9)	0.0082 (11)	0.0151 (11)
C32	0.0532 (14)	0.0470 (15)	0.0642 (17)	0.0012 (11)	0.0142 (13)	0.0201 (13)
C33	0.0498 (13)	0.0488 (14)	0.0513 (14)	0.0102 (11)	0.0038 (11)	0.0088 (12)
C34	0.0437 (12)	0.0555 (17)	0.0703 (18)	−0.0125 (11)	−0.0051 (12)	0.0120 (14)
C35	0.0457 (12)	0.0443 (14)	0.0563 (15)	−0.0075 (10)	0.0017 (11)	0.0168 (12)
C36	0.0369 (10)	0.0364 (12)	0.0532 (13)	0.0003 (8)	0.0110 (10)	−0.0011 (10)
C37	0.068 (2)	0.071 (2)	0.109 (3)	−0.0308 (16)	0.026 (2)	0.015 (2)
N1	0.0716 (14)	0.0342 (11)	0.0589 (14)	0.0197 (10)	0.0124 (11)	0.0003 (10)
N2	0.0430 (9)	0.0298 (10)	0.0463 (11)	0.0066 (7)	0.0086 (8)	0.0070 (8)
N3	0.0578 (12)	0.0345 (11)	0.0452 (11)	0.0106 (9)	0.0070 (9)	−0.0021 (9)
N4	0.0763 (15)	0.0329 (11)	0.0496 (12)	−0.0102 (10)	0.0087 (10)	0.0055 (9)
O1	0.0425 (9)	0.0822 (15)	0.0772 (14)	−0.0107 (9)	−0.0016 (9)	0.0147 (12)
O2	0.0468 (9)	0.0451 (10)	0.0736 (13)	−0.0128 (7)	0.0120 (8)	0.0133 (9)
O3	0.0954 (17)	0.0919 (17)	0.0507 (12)	−0.0014 (13)	0.0306 (12)	−0.0115 (11)
O4	0.0706 (12)	0.0474 (11)	0.0580 (11)	−0.0057 (9)	−0.0105 (9)	−0.0032 (9)
O5	0.115 (2)	0.0477 (12)	0.1045 (19)	−0.0364 (13)	0.0203 (16)	0.0114 (12)
O6	0.128 (3)	0.0694 (16)	0.109 (2)	0.0224 (17)	0.042 (2)	−0.0027 (15)
Br1	0.0742 (2)	0.0972 (3)	0.0835 (2)	0.00646 (19)	−0.01798 (16)	0.0311 (2)

C1—C2	1.351 (4)	C19—C20	1.364 (5)
C1—N1	1.370 (4)	C19—H19	0.9300
C1—H1	0.9300	C20—O6	1.371 (5)
C2—C3	1.419 (3)	C20—C21	1.397 (7)
C2—C9	1.500 (3)	C21—C22	1.364 (6)
C3—C4	1.398 (4)	C21—H21	0.9300
C3—C8	1.410 (3)	C22—H22	0.9300
C4—C5	1.371 (4)	C23—O6	1.420 (6)
C4—H4	0.9300	C23—H23A	0.9600
C5—C6	1.399 (5)	C23—H23B	0.9600
C5—H5	0.9300	C23—H23C	0.9600
C6—C7	1.359 (5)	C24—C25	1.379 (5)
C6—H6	0.9300	C24—C29	1.393 (4)
C7—C8	1.391 (4)	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.366 (6)
C8—N1	1.357 (4)	C25—H25	0.9300
C9—C10	1.540 (3)	C26—C27	1.369 (6)
C9—H9A	0.9700	C26—H26	0.9300
C9—H9B	0.9700	C27—C28	1.384 (5)
C10—N2	1.458 (3)	C27—H27	0.9300
C10—C36	1.529 (3)	C28—C29	1.393 (5)
C10—C11	1.600 (3)	C28—H28	0.9300
C11—C30	1.511 (3)	C30—C35	1.381 (3)
C11—C12	1.532 (3)	C30—C31	1.388 (3)
C11—H11	0.9800	C31—C32	1.369 (4)
C12—N3	1.505 (3)	C31—H31	0.9300
C12—C13	1.544 (3)	C32—C33	1.366 (4)
C12—H12	0.9800	C32—H32	0.9300
C13—N2	1.453 (3)	C33—C34	1.363 (4)
C13—C14	1.508 (3)	C33—Br1	1.895 (3)
C13—H13	0.9800	C34—C35	1.390 (4)
C14—N4	1.465 (3)	C34—H34	0.9300
C14—C15	1.576 (4)	C35—H35	0.9300
C14—H14	0.9800	C36—O1	1.180 (3)
C15—C29	1.498 (4)	C36—O2	1.325 (3)
C15—C16	1.529 (5)	C37—O2	1.458 (3)
C15—H15	0.9800	C37—H37A	0.9600
C16—O5	1.202 (4)	C37—H37B	0.9600
C16—N4	1.350 (4)	C37—H37C	0.9600
C17—C18	1.374 (5)	N1—H1A	0.8600
C17—C22	1.393 (5)	N2—H2	0.8600
C17—N4	1.408 (4)	N3—O3	1.210 (3)
C18—C19	1.377 (5)	N3—O4	1.218 (3)
C18—H18	0.9300
C2—C1—N1	110.1 (2)	C20—C19—H19	119.8
C2—C1—H1	125.0	C18—C19—H19	119.8
N1—C1—H1	125.0	C19—C20—O6	125.6 (4)
C1—C2—C3	106.7 (2)	C19—C20—C21	117.6 (4)
C1—C2—C9	126.7 (2)	O6—C20—C21	116.8 (3)
C3—C2—C9	126.6 (2)	C22—C21—C20	122.3 (3)
C4—C3—C8	118.6 (2)	C22—C21—H21	118.8
C4—C3—C2	134.5 (2)	C20—C21—H21	118.8
C8—C3—C2	106.9 (2)	C21—C22—C17	119.5 (4)
C5—C4—C3	119.2 (3)	C21—C22—H22	120.3
C5—C4—H4	120.4	C17—C22—H22	120.3
C3—C4—H4	120.4	O6—C23—H23A	109.5
C4—C5—C6	121.1 (3)	O6—C23—H23B	109.5
C4—C5—H5	119.5	H23A—C23—H23B	109.5
C6—C5—H5	119.5	O6—C23—H23C	109.5
C7—C6—C5	121.2 (2)	H23A—C23—H23C	109.5
C7—C6—H6	119.4	H23B—C23—H23C	109.5
C5—C6—H6	119.4	C25—C24—C29	121.2 (3)
C6—C7—C8	118.2 (3)	C25—C24—H24	119.4
C6—C7—H7	120.9	C29—C24—H24	119.4
C8—C7—H7	120.9	C26—C25—C24	121.1 (3)
N1—C8—C7	130.8 (2)	C26—C25—H25	119.5
N1—C8—C3	107.4 (2)	C24—C25—H25	119.5
C7—C8—C3	121.8 (3)	C25—C26—C27	118.4 (4)
C2—C9—C10	112.56 (19)	C25—C26—H26	120.8
C2—C9—H9A	109.1	C27—C26—H26	120.8
C10—C9—H9A	109.1	C26—C27—C28	121.7 (4)
C2—C9—H9B	109.1	C26—C27—H27	119.2
C10—C9—H9B	109.1	C28—C27—H27	119.2
H9A—C9—H9B	107.8	C27—C28—C29	120.3 (3)
N2—C10—C36	108.35 (18)	C27—C28—H28	119.9
N2—C10—C9	109.65 (18)	C29—C28—H28	119.9
C36—C10—C9	109.74 (18)	C24—C29—C28	117.3 (3)
N2—C10—C11	106.06 (16)	C24—C29—C15	121.5 (3)
C36—C10—C11	109.40 (17)	C28—C29—C15	121.2 (3)
C9—C10—C11	113.48 (17)	C35—C30—C31	117.5 (2)
C30—C11—C12	114.28 (18)	C35—C30—C11	124.2 (2)
C30—C11—C10	115.92 (18)	C31—C30—C11	118.3 (2)
C12—C11—C10	103.63 (16)	C32—C31—C30	121.4 (2)
C30—C11—H11	107.5	C32—C31—H31	119.3
C12—C11—H11	107.5	C30—C31—H31	119.3
C10—C11—H11	107.5	C33—C32—C31	119.9 (2)
N3—C12—C11	111.63 (18)	C33—C32—H32	120.0
N3—C12—C13	109.04 (19)	C31—C32—H32	120.0
C11—C12—C13	103.74 (18)	C34—C33—C32	120.7 (3)
N3—C12—H12	110.7	C34—C33—Br1	120.6 (2)
C11—C12—H12	110.7	C32—C33—Br1	118.8 (2)
C13—C12—H12	110.7	C33—C34—C35	119.3 (2)
N2—C13—C14	113.3 (2)	C33—C34—H34	120.4
N2—C13—C12	104.45 (17)	C35—C34—H34	120.4
C14—C13—C12	118.4 (2)	C30—C35—C34	121.3 (2)
N2—C13—H13	106.7	C30—C35—H35	119.4
C14—C13—H13	106.7	C34—C35—H35	119.4
C12—C13—H13	106.7	O1—C36—O2	124.4 (2)
N4—C14—C13	114.1 (2)	O1—C36—C10	125.0 (2)
N4—C14—C15	87.00 (18)	O2—C36—C10	110.6 (2)
C13—C14—C15	116.6 (2)	O2—C37—H37A	109.5
N4—C14—H14	112.3	O2—C37—H37B	109.5
C13—C14—H14	112.3	H37A—C37—H37B	109.5
C15—C14—H14	112.3	O2—C37—H37C	109.5
C29—C15—C16	115.9 (2)	H37A—C37—H37C	109.5
C29—C15—C14	120.7 (2)	H37B—C37—H37C	109.5
C16—C15—C14	84.4 (2)	C8—N1—C1	108.9 (2)
C29—C15—H15	111.1	C8—N1—H1A	125.5
C16—C15—H15	111.1	C1—N1—H1A	125.5
C14—C15—H15	111.1	C13—N2—C10	106.14 (17)
O5—C16—N4	131.8 (4)	C13—N2—H2	126.9
O5—C16—C15	135.1 (3)	C10—N2—H2	126.9
N4—C16—C15	93.1 (2)	O3—N3—O4	124.1 (2)
C18—C17—C22	118.0 (3)	O3—N3—C12	117.0 (2)
C18—C17—N4	122.2 (3)	O4—N3—C12	118.8 (2)
C22—C17—N4	119.8 (3)	C16—N4—C17	130.8 (2)
C17—C18—C19	122.1 (3)	C16—N4—C14	95.5 (2)
C17—C18—H18	119.0	C17—N4—C14	133.2 (2)
C19—C18—H18	119.0	C36—O2—C37	116.1 (3)
C20—C19—C18	120.4 (4)	C20—O6—C23	116.9 (3)
N1—C1—C2—C3	0.1 (3)	C24—C25—C26—C27	−2.3 (6)
N1—C1—C2—C9	−179.8 (2)	C25—C26—C27—C28	1.5 (6)
C1—C2—C3—C4	−179.9 (3)	C26—C27—C28—C29	−0.8 (5)
C9—C2—C3—C4	0.0 (4)	C25—C24—C29—C28	−1.5 (4)
C1—C2—C3—C8	0.0 (3)	C25—C24—C29—C15	−179.3 (3)
C9—C2—C3—C8	179.9 (2)	C27—C28—C29—C24	0.7 (4)
C8—C3—C4—C5	0.0 (4)	C27—C28—C29—C15	178.5 (3)
C2—C3—C4—C5	179.9 (3)	C16—C15—C29—C24	−21.8 (3)
C3—C4—C5—C6	−0.4 (4)	C14—C15—C29—C24	77.4 (3)
C4—C5—C6—C7	0.8 (5)	C16—C15—C29—C28	160.5 (3)
C5—C6—C7—C8	−0.8 (4)	C14—C15—C29—C28	−100.3 (3)
C6—C7—C8—N1	−179.4 (3)	C12—C11—C30—C35	−26.5 (3)
C6—C7—C8—C3	0.4 (4)	C10—C11—C30—C35	93.9 (3)
C4—C3—C8—N1	179.9 (2)	C12—C11—C30—C31	152.7 (2)
C2—C3—C8—N1	−0.1 (3)	C10—C11—C30—C31	−86.9 (3)
C4—C3—C8—C7	0.0 (4)	C35—C30—C31—C32	0.0 (4)
C2—C3—C8—C7	−179.9 (2)	C11—C30—C31—C32	−179.3 (2)
C1—C2—C9—C10	72.9 (3)	C30—C31—C32—C33	1.1 (4)
C3—C2—C9—C10	−107.0 (3)	C31—C32—C33—C34	−1.4 (5)
C2—C9—C10—N2	−65.0 (2)	C31—C32—C33—Br1	179.2 (2)
C2—C9—C10—C36	53.9 (2)	C32—C33—C34—C35	0.6 (5)
C2—C9—C10—C11	176.64 (18)	Br1—C33—C34—C35	179.9 (2)
N2—C10—C11—C30	−131.23 (19)	C31—C30—C35—C34	−0.8 (4)
C36—C10—C11—C30	112.1 (2)	C11—C30—C35—C34	178.4 (3)
C9—C10—C11—C30	−10.8 (2)	C33—C34—C35—C30	0.6 (5)
N2—C10—C11—C12	−5.2 (2)	N2—C10—C36—O1	−2.4 (3)
C36—C10—C11—C12	−121.86 (19)	C9—C10—C36—O1	−122.1 (3)
C9—C10—C11—C12	115.22 (19)	C11—C10—C36—O1	112.8 (3)
C30—C11—C12—N3	−133.95 (19)	N2—C10—C36—O2	178.07 (18)
C10—C11—C12—N3	98.99 (19)	C9—C10—C36—O2	58.4 (2)
C30—C11—C12—C13	108.8 (2)	C11—C10—C36—O2	−66.7 (2)
C10—C11—C12—C13	−18.3 (2)	C7—C8—N1—C1	179.9 (3)
N3—C12—C13—N2	−82.7 (2)	C3—C8—N1—C1	0.1 (3)
C11—C12—C13—N2	36.4 (2)	C2—C1—N1—C8	−0.1 (3)
N3—C12—C13—C14	44.5 (3)	C14—C13—N2—C10	−171.01 (19)
C11—C12—C13—C14	163.6 (2)	C12—C13—N2—C10	−40.8 (2)
N2—C13—C14—N4	−68.2 (3)	C36—C10—N2—C13	145.89 (18)
C12—C13—C14—N4	169.0 (2)	C9—C10—N2—C13	−94.4 (2)
N2—C13—C14—C15	−167.4 (2)	C11—C10—N2—C13	28.5 (2)
C12—C13—C14—C15	69.8 (3)	C11—C12—N3—O3	161.8 (2)
N4—C14—C15—C29	−116.5 (3)	C13—C12—N3—O3	−84.1 (3)
C13—C14—C15—C29	−1.0 (4)	C11—C12—N3—O4	−21.0 (3)
N4—C14—C15—C16	0.30 (19)	C13—C12—N3—O4	93.0 (2)
C13—C14—C15—C16	115.8 (2)	O5—C16—N4—C17	−8.2 (6)
C29—C15—C16—O5	−57.5 (5)	C15—C16—N4—C17	173.2 (3)
C14—C15—C16—O5	−178.9 (4)	O5—C16—N4—C14	179.0 (4)
C29—C15—C16—N4	121.1 (2)	C15—C16—N4—C14	0.4 (2)
C14—C15—C16—N4	−0.3 (2)	C18—C17—N4—C16	−147.7 (3)
C22—C17—C18—C19	−1.0 (5)	C22—C17—N4—C16	34.2 (5)
N4—C17—C18—C19	−179.1 (3)	C18—C17—N4—C14	22.5 (5)
C17—C18—C19—C20	−2.8 (6)	C22—C17—N4—C14	−155.6 (3)
C18—C19—C20—O6	−178.0 (4)	C13—C14—N4—C16	−118.3 (2)
C18—C19—C20—C21	4.1 (6)	C15—C14—N4—C16	−0.3 (2)
C19—C20—C21—C22	−1.8 (7)	C13—C14—N4—C17	69.2 (4)
O6—C20—C21—C22	−179.9 (4)	C15—C14—N4—C17	−172.9 (3)
C20—C21—C22—C17	−1.9 (7)	O1—C36—O2—C37	1.6 (4)
C18—C17—C22—C21	3.2 (6)	C10—C36—O2—C37	−178.9 (3)
N4—C17—C22—C21	−178.6 (4)	C19—C20—O6—C23	−17.0 (6)
C29—C24—C25—C26	2.4 (5)	C21—C20—O6—C23	161.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4	0.98	2.27	2.717 (3)	107
C4—H4···O4i	0.93	2.57	3.186 (3)	124
C31—H31···O4ii	0.93	2.55	3.399 (3)	152
N1—H1A···O5iii	0.86	2.02	2.820 (3)	155
C18—H18···Cgiv	0.93	2.80	3.641 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4	0.98	2.27	2.717 (3)	107
C4—H4⋯O4i	0.93	2.57	3.186 (3)	124
C31—H31⋯O4ii	0.93	2.55	3.399 (3)	152
N1—H1A⋯O5iii	0.86	2.02	2.820 (3)	155
C18—H18⋯Cgiv	0.93	2.80	3.641 (4)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg is the centroid of the indole benzene ring.