Crystal structure of ethyl 2-(2-{1-[N-(4-bromo-phen-yl)-2-oxo-2-phenyl-acetamido]-2-tert-butyl-amino-2-oxo-ethyl}-1H-pyrrol-1-yl)acetate.

In the title compound, C28H30BrN3O5, there is an intra-molecular N-H⋯O hydrogen bond and an intra-molecular C-H⋯O hydrogen bond, both forming S(9) ring motifs. The planes of the 4-bromo-phenyl ring and the phenyl ring are inclined to that of the pyrrole ring by 48.05 (12) and 77.45 (14)°, respectively, and to one another by 56.25 (12)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming slabs parallel to (10-1).

Related literature

For examples of the biological and pharmacological properties of pyrrole derivatives, see: Daidone et al. (1990 ▸); Davis et al. (2008 ▸); Kaiser & Glenn (1972 ▸); Meshram et al. (2010 ▸).

Experimental

Crystal data

C28H30BrN3O5

M = 568.46

Monoclinic,

a = 11.656 (3) Å

b = 17.997 (5) Å

c = 13.463 (4) Å

β = 97.351 (3)°

V = 2801.0 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.51 mm−1

T = 120 K

0.45 × 0.45 × 0.30 mm

Data collection

Bruker APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.600, T max = 0.636

25937 measured reflections

4924 independent reflections

3479 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.086

S = 1.35

4924 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015023592/su5258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023592/su5258Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup3.pdf

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup4.pdf

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015023592/su5258Isup5.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015023592/su5258fig1.tif

Mol­ecular structure and atom labelling for the title compound, with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015023592/su5258fig2.tif

Crystal packing of the title compound, viewed along the b axis, with the hydrogen bonds shown as dashed lines (see Table 1). H atoms not involved in these reactions have been omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S2056989015023592/su5258fig3.tif

Reaction scheme for the synthesis of the title compound.

CCDC reference: 1441330

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H30BrN3O5	F(000) = 1176
Mr = 568.46	Dx = 1.348 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.656 (3) Å	Cell parameters from 5570 reflections
b = 17.997 (5) Å	θ = 2.5–24.6°
c = 13.463 (4) Å	µ = 1.51 mm−1
β = 97.351 (3)°	T = 120 K
V = 2801.0 (14) Å3	Prism, colourless
Z = 4	0.45 × 0.45 × 0.30 mm

Bruker APEXII KappaCCD diffractometer	4924 independent reflections
Radiation source: fine focus sealed tube	3479 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 16.6666 pixels mm-1	θmax = 25.0°, θmin = 1.9°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→21
Tmin = 0.600, Tmax = 0.636	l = −15→15
25937 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.35	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
4924 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.38 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
Br1	0.68091 (3)	0.706481 (17)	−0.18700 (2)	0.07029 (14)
C1	0.8525 (2)	0.53075 (13)	0.23135 (16)	0.0383 (6)
C2	0.7777 (2)	0.58868 (14)	0.23617 (17)	0.0468 (6)
H2	0.6979	0.5871	0.2191	0.056*
C3	0.8433 (3)	0.65126 (15)	0.27172 (18)	0.0552 (7)
H3	0.8149	0.6985	0.2823	0.066*
C4	0.9549 (3)	0.62980 (15)	0.28746 (17)	0.0533 (7)
H4	1.017	0.66	0.3114	0.064*
C5	1.0655 (2)	0.51222 (14)	0.27953 (17)	0.0467 (7)
H5A	1.1321	0.5449	0.2907	0.056*
H5B	1.0727	0.483	0.2201	0.056*
C6	1.0659 (2)	0.46056 (14)	0.36869 (17)	0.0432 (6)
C7	1.1807 (2)	0.38299 (17)	0.4809 (2)	0.0665 (8)
H7B	1.124	0.3436	0.4684	0.08*
H7A	1.1667	0.4091	0.5412	0.08*
C8	1.2984 (2)	0.35156 (16)	0.4935 (2)	0.0660 (8)
H8A	1.3145	0.3306	0.4312	0.099*
H8B	1.304	0.3135	0.5439	0.099*
H8C	1.3534	0.3901	0.5137	0.099*
C9	0.82955 (19)	0.45262 (13)	0.19813 (15)	0.0356 (6)
H9	0.8958	0.4221	0.2256	0.043*
C10	0.7211 (2)	0.42272 (13)	0.23900 (17)	0.0403 (6)
C11	0.6458 (2)	0.39249 (15)	0.40046 (18)	0.0527 (7)
C12	0.7029 (3)	0.39672 (19)	0.50841 (19)	0.0840 (11)
H12A	0.7671	0.3629	0.5179	0.126*
H12B	0.6477	0.3835	0.5526	0.126*
H12C	0.7299	0.4464	0.5229	0.126*
C13	0.5479 (3)	0.44855 (17)	0.3815 (2)	0.0737 (9)
H13A	0.5786	0.4979	0.3912	0.111*
H13B	0.4927	0.4398	0.4274	0.111*
H13C	0.5106	0.4434	0.3141	0.111*
C14	0.6037 (3)	0.31320 (15)	0.3773 (2)	0.0644 (8)
H14A	0.5704	0.31	0.3084	0.097*
H14B	0.5464	0.3003	0.4196	0.097*
H14C	0.6678	0.2795	0.3893	0.097*
C15	0.78195 (19)	0.50735 (12)	0.02338 (15)	0.0328 (5)
C16	0.6698 (2)	0.51517 (13)	−0.02031 (16)	0.0377 (6)
H16	0.6142	0.4808	−0.007	0.045*
C17	0.6393 (2)	0.57413 (14)	−0.08427 (17)	0.0446 (6)
H17	0.5637	0.5792	−0.1154	0.054*
C18	0.7226 (2)	0.62508 (14)	−0.10092 (16)	0.0436 (6)
C19	0.8354 (2)	0.61903 (14)	−0.05585 (17)	0.0449 (6)
H19	0.8903	0.6545	−0.0673	0.054*
C20	0.8652 (2)	0.55931 (13)	0.00659 (16)	0.0394 (6)
H20	0.9408	0.554	0.0373	0.047*
C21	0.80952 (19)	0.37438 (14)	0.05223 (17)	0.0389 (6)
C22	0.7777 (2)	0.36402 (13)	−0.06085 (17)	0.0405 (6)
C23	0.6628 (2)	0.33239 (13)	−0.09648 (17)	0.0387 (6)
C24	0.5853 (2)	0.31256 (14)	−0.03116 (19)	0.0481 (7)
H24	0.6041	0.3202	0.0373	0.058*
C25	0.4805 (2)	0.28161 (16)	−0.0678 (2)	0.0592 (8)
H25	0.4284	0.2686	−0.0239	0.071*
C26	0.4525 (3)	0.26983 (16)	−0.1685 (2)	0.0647 (8)
H26	0.3824	0.2476	−0.1926	0.078*
C27	0.5275 (3)	0.29064 (18)	−0.2337 (2)	0.0677 (9)
H27	0.5077	0.2836	−0.3022	0.081*
C28	0.6322 (2)	0.32200 (16)	−0.19809 (19)	0.0563 (7)
H28	0.6827	0.3363	−0.2427	0.068*
N1	0.96215 (18)	0.55629 (11)	0.26258 (13)	0.0420 (5)
N2	0.73697 (18)	0.41127 (12)	0.33778 (14)	0.0479 (6)
H1	0.8065	0.4152	0.3676	0.058*
N3	0.81423 (15)	0.44477 (10)	0.08742 (13)	0.0355 (5)
O1	0.98294 (16)	0.44578 (10)	0.40912 (12)	0.0541 (5)
O2	1.17079 (15)	0.43440 (10)	0.39589 (12)	0.0526 (5)
O3	0.63055 (14)	0.41228 (10)	0.18436 (11)	0.0493 (4)
O4	0.83230 (15)	0.31985 (9)	0.10509 (12)	0.0515 (5)
O5	0.85012 (15)	0.37803 (10)	−0.11564 (12)	0.0549 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.0898 (3)	0.04937 (19)	0.0697 (2)	0.01077 (17)	0.00284 (17)	0.02204 (15)
C1	0.0429 (16)	0.0387 (14)	0.0316 (13)	−0.0043 (13)	−0.0016 (11)	0.0022 (11)
C2	0.0557 (18)	0.0452 (16)	0.0384 (14)	−0.0001 (14)	0.0023 (12)	0.0015 (12)
C3	0.081 (2)	0.0364 (16)	0.0478 (16)	−0.0010 (16)	0.0084 (15)	0.0010 (13)
C4	0.076 (2)	0.0399 (16)	0.0429 (15)	−0.0219 (15)	0.0035 (14)	0.0025 (12)
C5	0.0469 (17)	0.0518 (17)	0.0394 (14)	−0.0152 (14)	−0.0023 (12)	0.0049 (12)
C6	0.0448 (18)	0.0438 (16)	0.0380 (14)	−0.0120 (14)	−0.0066 (13)	−0.0004 (12)
C7	0.057 (2)	0.066 (2)	0.0742 (19)	−0.0068 (16)	−0.0008 (15)	0.0323 (17)
C8	0.062 (2)	0.0514 (18)	0.082 (2)	−0.0002 (16)	−0.0024 (15)	0.0152 (16)
C9	0.0368 (15)	0.0379 (14)	0.0306 (13)	−0.0007 (11)	−0.0022 (10)	−0.0003 (10)
C10	0.0466 (17)	0.0356 (14)	0.0382 (15)	−0.0044 (12)	0.0031 (12)	−0.0032 (11)
C11	0.068 (2)	0.0486 (17)	0.0437 (15)	−0.0187 (15)	0.0173 (13)	−0.0089 (13)
C12	0.124 (3)	0.088 (3)	0.0425 (17)	−0.040 (2)	0.0212 (17)	−0.0081 (16)
C13	0.091 (3)	0.0553 (19)	0.084 (2)	−0.0089 (18)	0.0465 (18)	−0.0154 (17)
C14	0.081 (2)	0.0512 (18)	0.0652 (19)	−0.0157 (16)	0.0241 (16)	−0.0086 (14)
C15	0.0346 (15)	0.0345 (13)	0.0283 (12)	0.0014 (11)	0.0009 (10)	−0.0007 (10)
C16	0.0365 (16)	0.0388 (14)	0.0369 (13)	−0.0008 (11)	0.0021 (11)	−0.0005 (11)
C17	0.0414 (16)	0.0472 (16)	0.0431 (14)	0.0068 (13)	−0.0027 (11)	0.0003 (13)
C18	0.0522 (18)	0.0384 (15)	0.0399 (14)	0.0056 (13)	0.0043 (12)	0.0055 (12)
C19	0.0489 (18)	0.0400 (15)	0.0468 (15)	−0.0070 (13)	0.0095 (12)	0.0016 (12)
C20	0.0353 (15)	0.0421 (15)	0.0399 (14)	0.0011 (12)	0.0012 (11)	0.0001 (12)
C21	0.0340 (15)	0.0404 (15)	0.0406 (14)	0.0002 (12)	−0.0011 (11)	−0.0007 (12)
C22	0.0484 (17)	0.0330 (14)	0.0398 (14)	0.0060 (12)	0.0040 (12)	−0.0015 (11)
C23	0.0409 (16)	0.0335 (14)	0.0399 (14)	0.0058 (12)	−0.0020 (12)	−0.0076 (11)
C24	0.0498 (18)	0.0460 (17)	0.0472 (16)	0.0023 (13)	0.0007 (13)	−0.0084 (12)
C25	0.0486 (18)	0.0570 (19)	0.071 (2)	−0.0040 (15)	0.0058 (15)	−0.0129 (15)
C26	0.0471 (19)	0.059 (2)	0.083 (2)	0.0073 (15)	−0.0148 (17)	−0.0252 (17)
C27	0.056 (2)	0.089 (2)	0.0525 (18)	0.0081 (18)	−0.0132 (16)	−0.0246 (17)
C28	0.0539 (19)	0.068 (2)	0.0448 (16)	0.0059 (15)	−0.0004 (13)	−0.0126 (14)
N1	0.0485 (14)	0.0392 (12)	0.0361 (11)	−0.0104 (11)	−0.0027 (9)	0.0031 (9)
N2	0.0511 (14)	0.0567 (14)	0.0351 (12)	−0.0170 (11)	0.0024 (9)	−0.0014 (10)
N3	0.0380 (12)	0.0343 (11)	0.0326 (10)	−0.0010 (9)	−0.0020 (8)	−0.0003 (9)
O1	0.0468 (12)	0.0684 (13)	0.0452 (10)	−0.0127 (10)	−0.0012 (9)	0.0141 (9)
O2	0.0476 (12)	0.0515 (11)	0.0571 (11)	−0.0090 (9)	0.0007 (9)	0.0161 (9)
O3	0.0387 (11)	0.0630 (12)	0.0442 (10)	−0.0074 (9)	−0.0022 (8)	−0.0044 (8)
O4	0.0670 (13)	0.0364 (10)	0.0467 (10)	0.0033 (9)	−0.0097 (9)	0.0027 (8)
O5	0.0546 (12)	0.0659 (13)	0.0456 (10)	−0.0043 (10)	0.0113 (9)	−0.0064 (9)

Br1—C18	1.893 (2)	C13—H13A	0.96
C1—C2	1.365 (3)	C13—H13B	0.96
C1—N1	1.373 (3)	C13—H13C	0.96
C1—C9	1.489 (3)	C14—H14A	0.96
C2—C3	1.410 (3)	C14—H14B	0.96
C2—H2	0.93	C14—H14C	0.96
C3—C4	1.347 (4)	C15—C16	1.370 (3)
C3—H3	0.93	C15—C20	1.387 (3)
C4—N1	1.370 (3)	C15—N3	1.439 (3)
C4—H4	0.93	C16—C17	1.384 (3)
C5—N1	1.436 (3)	C16—H16	0.93
C5—C6	1.518 (3)	C17—C18	1.375 (3)
C5—H5A	0.97	C17—H17	0.93
C5—H5B	0.97	C18—C19	1.380 (3)
C6—O1	1.198 (3)	C19—C20	1.381 (3)
C6—O2	1.318 (3)	C19—H19	0.93
C7—O2	1.465 (3)	C20—H20	0.93
C7—C8	1.473 (4)	C21—O4	1.221 (3)
C7—H7B	0.97	C21—N3	1.351 (3)
C7—H7A	0.97	C21—C22	1.532 (3)
C8—H8A	0.96	C22—O5	1.216 (3)
C8—H8B	0.96	C22—C23	1.477 (3)
C8—H8C	0.96	C23—C28	1.382 (3)
C9—N3	1.485 (3)	C23—C24	1.386 (3)
C9—C10	1.539 (3)	C24—C25	1.375 (4)
C9—H9	0.98	C24—H24	0.93
C10—O3	1.221 (3)	C25—C26	1.371 (4)
C10—N2	1.335 (3)	C25—H25	0.93
C11—N2	1.479 (3)	C26—C27	1.368 (4)
C11—C13	1.520 (4)	C26—H26	0.93
C11—C12	1.521 (4)	C27—C28	1.373 (4)
C11—C14	1.528 (3)	C27—H27	0.93
C12—H12A	0.96	C28—H28	0.93
C12—H12B	0.96	N2—H1	0.86
C12—H12C	0.96
C2—C1—N1	107.7 (2)	H13B—C13—H13C	109.5
C2—C1—C9	130.1 (2)	C11—C14—H14A	109.5
N1—C1—C9	122.2 (2)	C11—C14—H14B	109.5
C1—C2—C3	107.7 (2)	H14A—C14—H14B	109.5
C1—C2—H2	126.1	C11—C14—H14C	109.5
C3—C2—H2	126.1	H14A—C14—H14C	109.5
C4—C3—C2	107.2 (3)	H14B—C14—H14C	109.5
C4—C3—H3	126.4	C16—C15—C20	120.6 (2)
C2—C3—H3	126.4	C16—C15—N3	120.0 (2)
C3—C4—N1	109.1 (2)	C20—C15—N3	119.4 (2)
C3—C4—H4	125.5	C15—C16—C17	120.1 (2)
N1—C4—H4	125.5	C15—C16—H16	120.0
N1—C5—C6	112.4 (2)	C17—C16—H16	120.0
N1—C5—H5A	109.1	C18—C17—C16	118.8 (2)
C6—C5—H5A	109.1	C18—C17—H17	120.6
N1—C5—H5B	109.1	C16—C17—H17	120.6
C6—C5—H5B	109.1	C17—C18—C19	121.9 (2)
H5A—C5—H5B	107.9	C17—C18—Br1	118.99 (19)
O1—C6—O2	124.6 (2)	C19—C18—Br1	119.08 (19)
O1—C6—C5	125.1 (2)	C18—C19—C20	118.7 (2)
O2—C6—C5	110.3 (2)	C18—C19—H19	120.7
O2—C7—C8	108.2 (2)	C20—C19—H19	120.7
O2—C7—H7B	110.1	C19—C20—C15	119.8 (2)
C8—C7—H7B	110.1	C19—C20—H20	120.1
O2—C7—H7A	110.1	C15—C20—H20	120.1
C8—C7—H7A	110.1	O4—C21—N3	123.6 (2)
H7B—C7—H7A	108.4	O4—C21—C22	119.2 (2)
C7—C8—H8A	109.5	N3—C21—C22	117.2 (2)
C7—C8—H8B	109.5	O5—C22—C23	123.6 (2)
H8A—C8—H8B	109.5	O5—C22—C21	118.6 (2)
C7—C8—H8C	109.5	C23—C22—C21	117.6 (2)
H8A—C8—H8C	109.5	C28—C23—C24	119.1 (2)
H8B—C8—H8C	109.5	C28—C23—C22	118.8 (2)
N3—C9—C1	112.66 (18)	C24—C23—C22	122.1 (2)
N3—C9—C10	109.08 (17)	C25—C24—C23	119.9 (2)
C1—C9—C10	110.28 (18)	C25—C24—H24	120.1
N3—C9—H9	108.2	C23—C24—H24	120.1
C1—C9—H9	108.2	C26—C25—C24	120.4 (3)
C10—C9—H9	108.2	C26—C25—H25	119.8
O3—C10—N2	125.1 (2)	C24—C25—H25	119.8
O3—C10—C9	121.6 (2)	C27—C26—C25	120.1 (3)
N2—C10—C9	113.2 (2)	C27—C26—H26	119.9
N2—C11—C13	109.4 (2)	C25—C26—H26	119.9
N2—C11—C12	106.0 (2)	C26—C27—C28	120.0 (3)
C13—C11—C12	110.7 (2)	C26—C27—H27	120.0
N2—C11—C14	109.4 (2)	C28—C27—H27	120.0
C13—C11—C14	111.8 (2)	C27—C28—C23	120.5 (3)
C12—C11—C14	109.4 (2)	C27—C28—H28	119.8
C11—C12—H12A	109.5	C23—C28—H28	119.8
C11—C12—H12B	109.5	C4—N1—C1	108.3 (2)
H12A—C12—H12B	109.5	C4—N1—C5	124.8 (2)
C11—C12—H12C	109.5	C1—N1—C5	126.4 (2)
H12A—C12—H12C	109.5	C10—N2—C11	125.8 (2)
H12B—C12—H12C	109.5	C10—N2—H1	117.1
C11—C13—H13A	109.5	C11—N2—H1	117.1
C11—C13—H13B	109.5	C21—N3—C15	121.87 (18)
H13A—C13—H13B	109.5	C21—N3—C9	115.81 (18)
C11—C13—H13C	109.5	C15—N3—C9	121.04 (17)
H13A—C13—H13C	109.5	C6—O2—C7	114.86 (19)
N1—C1—C2—C3	−0.3 (3)	C23—C24—C25—C26	0.4 (4)
C9—C1—C2—C3	−179.3 (2)	C24—C25—C26—C27	−1.7 (4)
C1—C2—C3—C4	−0.1 (3)	C25—C26—C27—C28	1.3 (5)
C2—C3—C4—N1	0.4 (3)	C26—C27—C28—C23	0.4 (4)
N1—C5—C6—O1	14.3 (3)	C24—C23—C28—C27	−1.7 (4)
N1—C5—C6—O2	−165.40 (19)	C22—C23—C28—C27	178.0 (3)
C2—C1—C9—N3	79.9 (3)	C3—C4—N1—C1	−0.6 (3)
N1—C1—C9—N3	−99.0 (2)	C3—C4—N1—C5	−173.0 (2)
C2—C1—C9—C10	−42.2 (3)	C2—C1—N1—C4	0.5 (2)
N1—C1—C9—C10	138.9 (2)	C9—C1—N1—C4	179.64 (19)
N3—C9—C10—O3	−15.8 (3)	C2—C1—N1—C5	172.8 (2)
C1—C9—C10—O3	108.4 (2)	C9—C1—N1—C5	−8.0 (3)
N3—C9—C10—N2	165.23 (19)	C6—C5—N1—C4	103.3 (3)
C1—C9—C10—N2	−70.6 (3)	C6—C5—N1—C1	−67.8 (3)
C20—C15—C16—C17	1.9 (3)	O3—C10—N2—C11	−7.5 (4)
N3—C15—C16—C17	−178.1 (2)	C9—C10—N2—C11	171.4 (2)
C15—C16—C17—C18	−1.5 (3)	C13—C11—N2—C10	−52.2 (3)
C16—C17—C18—C19	0.0 (4)	C12—C11—N2—C10	−171.6 (2)
C16—C17—C18—Br1	−179.23 (17)	C14—C11—N2—C10	70.6 (3)
C17—C18—C19—C20	1.0 (4)	O4—C21—N3—C15	−177.3 (2)
Br1—C18—C19—C20	−179.78 (17)	C22—C21—N3—C15	4.8 (3)
C18—C19—C20—C15	−0.5 (3)	O4—C21—N3—C9	−10.1 (3)
C16—C15—C20—C19	−0.9 (3)	C22—C21—N3—C9	172.03 (19)
N3—C15—C20—C19	179.1 (2)	C16—C15—N3—C21	64.9 (3)
O4—C21—C22—O5	−102.8 (3)	C20—C15—N3—C21	−115.1 (2)
N3—C21—C22—O5	75.1 (3)	C16—C15—N3—C9	−101.6 (2)
O4—C21—C22—C23	73.0 (3)	C20—C15—N3—C9	78.4 (3)
N3—C21—C22—C23	−109.1 (2)	C1—C9—N3—C21	171.0 (2)
O5—C22—C23—C28	−4.0 (4)	C10—C9—N3—C21	−66.2 (2)
C21—C22—C23—C28	−179.6 (2)	C1—C9—N3—C15	−21.7 (3)
O5—C22—C23—C24	175.7 (2)	C10—C9—N3—C15	101.1 (2)
C21—C22—C23—C24	0.1 (3)	O1—C6—O2—C7	1.0 (3)
C28—C23—C24—C25	1.3 (4)	C5—C6—O2—C7	−179.3 (2)
C22—C23—C24—C25	−178.4 (2)	C8—C7—O2—C6	172.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1	0.86	2.13	2.970 (3)	164
C14—H24···O3	0.93	2.57	3.199 (3)	148
C8—H8B···O4i	0.96	2.55	3.432 (3)	154
C17—H17···O3ii	0.93	2.34	3.269 (3)	176
C7—H7A···Cg1iii	0.97	2.86	3.697 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1	0.86	2.13	2.970 (3)	164
C14—H24⋯O3	0.93	2.57	3.199 (3)	148
C8—H8B⋯O4i	0.96	2.55	3.432 (3)	154
C17—H17⋯O3ii	0.93	2.34	3.269 (3)	176
C7—H7A⋯Cg1iii	0.97	2.86	3.697 (3)	151

Symmetry codes: (i) ; (ii) ; (iii) .