N-[(6-Bromo-2-meth-oxy-3-quinol-yl)phenyl-meth-yl]-2-morpholino-N-(1-phenyl-ethyl)acetamide.

In the title compound, C(31)H(32)BrN(3)O(3), the morpholine ring adopts a chair conformation, and the planar quinoline system is twisted with respect to the phenyl rings, with dihedral angles of 17.6 (4) and 75.1 (3)°. Intramolecular C-H⋯O and C-H⋯N hydrogen bonds are present. The crystal packing is stabilized by weak C-H⋯O hydrogen bonding and C-H⋯π interactions.

Related literature

For the synthesis of other phamaceutically active derivatives through conventional and other synthetic routes, see: Andries et al. (2005 ▶); Gaurrand et al. (2006 ▶); Mao et al. (2007 ▶); Dalla Via et al. (2008 ▶). For related structures, see: Petit et al. (2007 ▶); Rahmani et al. (2009 ▶).

Experimental

Crystal data

C31H32BrN3O3

M = 574.50

Triclinic,

a = 7.8696 (14) Å

b = 9.4558 (16) Å

c = 9.8018 (17) Å

α = 90.544 (2)°

β = 100.562 (3)°

γ = 104.618 (2)°

V = 692.6 (2) Å3

Z = 1

Mo Kα radiation

μ = 1.52 mm−1

T = 298 K

0.45 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.525, T max = 0.625

4628 measured reflections

3796 independent reflections

2917 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.236

S = 1.02

3796 reflections

346 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1149 Friedel pairs

Flack parameter: 0.14 (2)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027020/xu2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027020/xu2541Isup2.hkl

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

C31H32BrN3O3	Z = 1
Mr = 574.50	F(000) = 298
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8696 (14) Å	Cell parameters from 3537 reflections
b = 9.4558 (16) Å	θ = 2.1–25.9°
c = 9.8018 (17) Å	µ = 1.52 mm−1
α = 90.544 (2)°	T = 298 K
β = 100.562 (3)°	Prism, colorless
γ = 104.618 (2)°	0.45 × 0.33 × 0.31 mm
V = 692.6 (2) Å3

Bruker SMART APEX CCD diffractometer	3796 independent reflections
Radiation source: fine-focus sealed tube	2917 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.525, Tmax = 0.625	k = −11→11
4628 measured reflections	l = −10→12

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)] = 0.076	H-atom parameters constrained
wR(F2) = 0.236	w = 1/[σ2(Fo2) + (0.1743P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3796 reflections	Δρmax = 0.66 e Å−3
346 parameters	Δρmin = −0.46 e Å−3
4 restraints	Absolute structure: Flack (1983), 1149 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.14 (2)

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	1.24839 (17)	0.39015 (15)	−0.05433 (14)	0.1036 (5)
C4	0.3479 (12)	−0.0267 (12)	0.8340 (10)	0.072 (2)
H4A	0.3364	0.0712	0.8523	0.087*
H4B	0.2288	−0.0899	0.8016	0.087*
C3	0.4565 (11)	−0.0236 (10)	0.7234 (9)	0.0593 (19)
H3A	0.4610	−0.1223	0.6999	0.071*
H3B	0.4007	0.0147	0.6404	0.071*
C1	0.5983 (15)	0.0096 (16)	1.0047 (11)	0.093 (3)
H1A	0.6513	−0.0286	1.0889	0.111*
H1B	0.5928	0.1083	1.0274	0.111*
C2	0.7147 (14)	0.0142 (12)	0.8971 (10)	0.078 (3)
H2A	0.8328	0.0777	0.9322	0.093*
H2B	0.7273	−0.0833	0.8788	0.093*
C5	0.7473 (10)	0.0755 (8)	0.6650 (7)	0.0459 (16)
H5A	0.7580	−0.0218	0.6433	0.055*
H5B	0.8664	0.1365	0.7020	0.055*
C6	0.6689 (8)	0.1390 (6)	0.5298 (6)	0.0317 (12)
C7	0.5793 (12)	0.4161 (8)	0.7307 (9)	0.060 (2)
H7A	0.5232	0.4804	0.6745	0.090*
H7B	0.6332	0.4632	0.8210	0.090*
H7C	0.4911	0.3276	0.7400	0.090*
C8	0.7214 (9)	0.3799 (6)	0.6625 (6)	0.0373 (14)
H8	0.7906	0.3306	0.7307	0.045*
C9	0.8530 (10)	0.5077 (7)	0.6180 (6)	0.0398 (14)
C14	1.0104 (10)	0.4857 (8)	0.5883 (9)	0.0508 (16)
H14	1.0386	0.3971	0.6065	0.061*
C13	1.1252 (11)	0.5939 (9)	0.5320 (10)	0.059 (2)
H13	1.2287	0.5758	0.5112	0.070*
C12	1.0920 (12)	0.7264 (8)	0.5058 (10)	0.063 (2)
H12	1.1741	0.7998	0.4721	0.076*
C11	0.9277 (13)	0.7502 (8)	0.5314 (11)	0.066 (2)
H11	0.8944	0.8352	0.5058	0.079*
C10	0.8187 (11)	0.6417 (7)	0.5959 (9)	0.0532 (18)
H10	0.7201	0.6609	0.6246	0.064*
C15	0.5369 (8)	0.3306 (6)	0.4201 (6)	0.0350 (13)
H15	0.4995	0.4106	0.4600	0.042*
C17	0.6440 (8)	0.4009 (6)	0.3131 (6)	0.0332 (13)
C18	0.6119 (8)	0.5339 (6)	0.2557 (6)	0.0328 (12)
C19	0.8276 (8)	0.5586 (6)	0.1238 (6)	0.0353 (13)
C20	0.9212 (10)	0.6379 (8)	0.0287 (7)	0.0461 (16)
H20	0.8967	0.7252	−0.0003	0.055*
C21	1.0491 (11)	0.5886 (8)	−0.0229 (8)	0.0540 (18)
H21	1.1107	0.6423	−0.0859	0.065*
C22	1.0847 (9)	0.4566 (8)	0.0209 (7)	0.0498 (17)
C23	0.9987 (10)	0.3773 (7)	0.1165 (7)	0.0419 (14)
H23	1.0267	0.2912	0.1457	0.050*
C24	0.8690 (8)	0.4261 (6)	0.1699 (6)	0.0357 (13)
C25	0.7735 (8)	0.3516 (6)	0.2667 (6)	0.0323 (12)
H25	0.7992	0.2662	0.3004	0.039*
C26	0.4505 (13)	0.7175 (8)	0.2544 (10)	0.067 (2)
H26A	0.5093	0.7945	0.3245	0.101*
H26B	0.3242	0.7092	0.2360	0.101*
H26C	0.4966	0.7396	0.1707	0.101*
C31	0.2225 (10)	0.1953 (8)	0.4322 (9)	0.0499 (17)
H31	0.2364	0.2511	0.5141	0.060*
C30	0.0646 (10)	0.0914 (9)	0.3835 (11)	0.062 (2)
H30	−0.0274	0.0771	0.4335	0.074*
C29	0.0405 (10)	0.0078 (10)	0.2614 (12)	0.065 (2)
H29	−0.0676	−0.0608	0.2286	0.078*
C28	0.1781 (13)	0.0275 (10)	0.1892 (11)	0.072 (3)
H28	0.1658	−0.0303	0.1090	0.086*
C27	0.3378 (8)	0.1360 (7)	0.2379 (8)	0.0468 (16)
H27	0.4287	0.1530	0.1867	0.056*
C32	0.3609 (9)	0.2165 (7)	0.3588 (7)	0.0383 (14)
N1	0.7011 (8)	0.6132 (5)	0.1700 (6)	0.0387 (12)
N2	0.6404 (7)	0.2747 (5)	0.5409 (5)	0.0327 (10)
N3	0.6363 (7)	0.0673 (5)	0.7712 (6)	0.0411 (12)
O1	0.4833 (7)	0.5790 (4)	0.3030 (5)	0.0468 (12)
O2	0.6376 (6)	0.0666 (4)	0.4219 (5)	0.0418 (10)
O3	0.4266 (10)	−0.0772 (9)	0.9568 (7)	0.088 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.1037 (8)	0.1453 (11)	0.0862 (8)	0.0497 (7)	0.0549 (6)	0.0297 (7)
C4	0.056 (5)	0.088 (6)	0.069 (6)	−0.001 (4)	0.029 (4)	0.021 (5)
C3	0.058 (5)	0.071 (5)	0.048 (4)	0.009 (4)	0.017 (3)	0.017 (4)
C1	0.074 (7)	0.142 (9)	0.057 (6)	0.010 (7)	0.025 (5)	0.039 (6)
C2	0.090 (7)	0.089 (6)	0.050 (5)	0.011 (5)	0.016 (5)	0.042 (5)
C5	0.052 (4)	0.058 (4)	0.041 (4)	0.028 (3)	0.024 (3)	0.021 (3)
C6	0.036 (3)	0.029 (3)	0.035 (3)	0.010 (2)	0.018 (2)	0.012 (2)
C7	0.077 (5)	0.050 (4)	0.053 (5)	−0.005 (4)	0.043 (4)	−0.015 (3)
C8	0.049 (4)	0.035 (3)	0.027 (3)	0.005 (3)	0.014 (3)	0.004 (2)
C9	0.055 (4)	0.037 (3)	0.026 (3)	0.008 (3)	0.009 (3)	0.001 (2)
C14	0.048 (4)	0.049 (4)	0.058 (5)	0.011 (3)	0.020 (3)	0.012 (3)
C13	0.039 (4)	0.071 (5)	0.073 (6)	0.015 (3)	0.029 (4)	0.024 (4)
C12	0.071 (5)	0.049 (4)	0.064 (5)	−0.002 (4)	0.021 (4)	0.004 (4)
C11	0.080 (6)	0.039 (3)	0.084 (6)	0.006 (4)	0.042 (5)	0.015 (4)
C10	0.061 (4)	0.041 (3)	0.067 (5)	0.015 (3)	0.034 (4)	0.001 (3)
C15	0.043 (3)	0.033 (3)	0.037 (3)	0.017 (2)	0.020 (3)	0.014 (2)
C17	0.042 (3)	0.028 (3)	0.029 (3)	0.005 (2)	0.009 (2)	0.005 (2)
C18	0.032 (3)	0.032 (3)	0.034 (3)	0.007 (2)	0.010 (2)	0.007 (2)
C19	0.039 (3)	0.039 (3)	0.024 (3)	0.001 (2)	0.008 (2)	0.008 (2)
C20	0.052 (4)	0.048 (3)	0.038 (4)	0.005 (3)	0.018 (3)	0.019 (3)
C21	0.071 (5)	0.058 (4)	0.038 (4)	0.009 (4)	0.033 (3)	0.026 (3)
C22	0.044 (4)	0.071 (5)	0.035 (4)	0.010 (3)	0.018 (3)	0.008 (3)
C23	0.048 (4)	0.051 (3)	0.032 (3)	0.016 (3)	0.019 (3)	0.014 (3)
C24	0.036 (3)	0.040 (3)	0.028 (3)	0.005 (2)	0.005 (2)	0.005 (2)
C25	0.037 (3)	0.035 (3)	0.032 (3)	0.011 (2)	0.020 (2)	0.017 (2)
C26	0.087 (6)	0.051 (4)	0.093 (7)	0.046 (4)	0.051 (5)	0.045 (4)
C31	0.056 (4)	0.052 (4)	0.058 (4)	0.029 (3)	0.031 (3)	0.023 (3)
C30	0.034 (4)	0.061 (4)	0.102 (7)	0.017 (3)	0.033 (4)	0.048 (5)
C29	0.036 (4)	0.064 (5)	0.090 (7)	0.003 (3)	0.012 (4)	0.031 (5)
C28	0.067 (6)	0.066 (5)	0.065 (6)	−0.002 (4)	−0.003 (5)	0.000 (4)
C27	0.026 (3)	0.058 (4)	0.055 (4)	0.000 (3)	0.018 (3)	0.003 (3)
C32	0.036 (3)	0.044 (3)	0.040 (4)	0.014 (3)	0.015 (3)	0.017 (3)
N1	0.045 (3)	0.037 (2)	0.034 (3)	0.005 (2)	0.015 (2)	0.009 (2)
N2	0.040 (3)	0.035 (2)	0.025 (2)	0.009 (2)	0.013 (2)	0.0047 (19)
N3	0.047 (3)	0.041 (3)	0.038 (3)	0.011 (2)	0.014 (2)	0.012 (2)
O1	0.062 (3)	0.036 (2)	0.055 (3)	0.023 (2)	0.030 (2)	0.021 (2)
O2	0.049 (3)	0.037 (2)	0.044 (3)	0.0130 (19)	0.018 (2)	0.0039 (19)
O3	0.090 (5)	0.117 (5)	0.062 (4)	0.017 (4)	0.036 (4)	0.051 (4)

Br1—C22	1.829 (8)	C15—N2	1.490 (8)
C4—O3	1.396 (12)	C15—C17	1.519 (9)
C4—C3	1.495 (13)	C15—C32	1.540 (9)
C4—H4A	0.9700	C15—H15	0.9800
C4—H4B	0.9700	C17—C25	1.367 (9)
C3—N3	1.448 (10)	C17—C18	1.444 (8)
C3—H3A	0.9700	C18—N1	1.313 (8)
C3—H3B	0.9700	C18—N1	1.313 (8)
C1—O3	1.386 (13)	C18—O1	1.344 (8)
C1—C2	1.513 (16)	C19—N1	1.372 (9)
C1—H1A	0.9700	C19—N1	1.372 (9)
C1—H1B	0.9700	C19—C20	1.400 (9)
C2—N3	1.430 (10)	C19—C24	1.429 (8)
C2—H2A	0.9700	C20—C21	1.380 (11)
C2—H2B	0.9700	C20—H20	0.9300
C5—N3	1.468 (9)	C21—C22	1.402 (11)
C5—C6	1.549 (8)	C21—H21	0.9300
C5—H5A	0.9700	C22—C23	1.374 (10)
C5—H5B	0.9700	C23—C24	1.400 (10)
C6—O2	1.206 (8)	C23—H23	0.9300
C6—O2	1.206 (8)	C24—C25	1.403 (9)
C6—N2	1.364 (7)	C25—H25	0.9300
C7—C8	1.509 (10)	C26—O1	1.465 (7)
C7—H7A	0.9600	C26—H26A	0.9600
C7—H7B	0.9600	C26—H26B	0.9600
C7—H7C	0.9600	C26—H26C	0.9600
C8—N2	1.482 (8)	C31—C30	1.377 (12)
C8—C9	1.506 (9)	C31—C32	1.387 (10)
C8—H8	0.9800	C31—H31	0.9300
C9—C10	1.372 (9)	C30—C29	1.384 (15)
C9—C14	1.387 (10)	C30—H30	0.9300
C14—C13	1.376 (12)	C29—C28	1.375 (14)
C14—H14	0.9300	C29—H29	0.9300
C13—C12	1.361 (12)	C28—C27	1.407 (11)
C13—H13	0.9300	C28—H28	0.9300
C12—C11	1.431 (13)	C27—C32	1.360 (11)
C12—H12	0.9300	C27—H27	0.9300
C11—C10	1.398 (12)	N1—N1	0.000
C11—H11	0.9300	O2—O2	0.000
C10—H10	0.9300
O3—C4—C3	111.4 (8)	N2—C15—H15	104.8
O3—C4—H4A	109.3	C17—C15—H15	104.8
C3—C4—H4A	109.3	C32—C15—H15	104.8
O3—C4—H4B	109.3	C25—C17—C18	115.7 (5)
C3—C4—H4B	109.3	C25—C17—C15	125.9 (5)
H4A—C4—H4B	108.0	C18—C17—C15	118.4 (5)
N3—C3—C4	110.2 (7)	N1—C18—O1	119.9 (5)
N3—C3—H3A	109.6	N1—C18—O1	119.9 (5)
C4—C3—H3A	109.6	N1—C18—C17	125.8 (6)
N3—C3—H3B	109.6	N1—C18—C17	125.8 (6)
C4—C3—H3B	109.6	O1—C18—C17	114.1 (5)
H3A—C3—H3B	108.1	N1—C19—C20	118.1 (6)
O3—C1—C2	111.4 (10)	N1—C19—C20	118.1 (6)
O3—C1—H1A	109.4	N1—C19—C24	122.9 (6)
C2—C1—H1A	109.4	N1—C19—C24	122.9 (6)
O3—C1—H1B	109.4	C20—C19—C24	118.9 (6)
C2—C1—H1B	109.4	C21—C20—C19	121.2 (6)
H1A—C1—H1B	108.0	C21—C20—H20	119.4
N3—C2—C1	110.1 (8)	C19—C20—H20	119.4
N3—C2—H2A	109.6	C20—C21—C22	119.0 (6)
C1—C2—H2A	109.6	C20—C21—H21	120.5
N3—C2—H2B	109.6	C22—C21—H21	120.5
C1—C2—H2B	109.6	C23—C22—C21	121.6 (7)
H2A—C2—H2B	108.2	C23—C22—Br1	120.3 (6)
N3—C5—C6	112.5 (5)	C21—C22—Br1	118.1 (5)
N3—C5—H5A	109.1	C22—C23—C24	119.9 (6)
C6—C5—H5A	109.1	C22—C23—H23	120.0
N3—C5—H5B	109.1	C24—C23—H23	120.0
C6—C5—H5B	109.1	C23—C24—C25	123.8 (5)
H5A—C5—H5B	107.8	C23—C24—C19	119.3 (6)
O2—C6—N2	124.1 (5)	C25—C24—C19	116.9 (6)
O2—C6—N2	124.1 (5)	C17—C25—C24	121.9 (5)
O2—C6—C5	118.5 (5)	C17—C25—H25	119.0
O2—C6—C5	118.5 (5)	C24—C25—H25	119.0
N2—C6—C5	117.4 (5)	O1—C26—H26A	109.5
C8—C7—H7A	109.5	O1—C26—H26B	109.5
C8—C7—H7B	109.5	H26A—C26—H26B	109.5
H7A—C7—H7B	109.5	O1—C26—H26C	109.5
C8—C7—H7C	109.5	H26A—C26—H26C	109.5
H7A—C7—H7C	109.5	H26B—C26—H26C	109.5
H7B—C7—H7C	109.5	C30—C31—C32	119.8 (8)
N2—C8—C9	108.4 (5)	C30—C31—H31	120.1
N2—C8—C7	111.1 (5)	C32—C31—H31	120.1
C9—C8—C7	116.3 (5)	C31—C30—C29	121.1 (8)
N2—C8—H8	106.9	C31—C30—H30	119.4
C9—C8—H8	106.9	C29—C30—H30	119.4
C7—C8—H8	106.9	C28—C29—C30	119.2 (8)
C10—C9—C14	118.5 (7)	C28—C29—H29	120.4
C10—C9—C8	123.0 (6)	C30—C29—H29	120.4
C14—C9—C8	118.3 (6)	C29—C28—C27	119.4 (9)
C13—C14—C9	120.5 (7)	C29—C28—H28	120.3
C13—C14—H14	119.7	C27—C28—H28	120.3
C9—C14—H14	119.7	C32—C27—C28	120.9 (8)
C12—C13—C14	122.1 (8)	C32—C27—H27	119.5
C12—C13—H13	119.0	C28—C27—H27	119.5
C14—C13—H13	119.0	C27—C32—C31	119.5 (6)
C13—C12—C11	118.4 (8)	C27—C32—C15	122.7 (6)
C13—C12—H12	120.8	C31—C32—C15	117.7 (6)
C11—C12—H12	120.8	C18—N1—C19	116.6 (5)
C10—C11—C12	118.1 (7)	C6—N2—C8	124.1 (5)
C10—C11—H11	121.0	C6—N2—C15	119.7 (5)
C12—C11—H11	121.0	C8—N2—C15	115.9 (4)
C9—C10—C11	121.9 (7)	C2—N3—C3	109.3 (6)
C9—C10—H10	119.0	C2—N3—C5	111.6 (6)
C11—C10—H10	119.0	C3—N3—C5	112.2 (6)
N2—C15—C17	115.4 (5)	C18—O1—C26	116.8 (5)
N2—C15—C32	111.3 (5)	C1—O3—C4	110.7 (7)
C17—C15—C32	114.6 (5)
O3—C4—C3—N3	−57.5 (10)	C31—C30—C29—C28	1.2 (11)
O3—C1—C2—N3	57.8 (12)	C30—C29—C28—C27	−2.5 (12)
N3—C5—C6—O2	−123.0 (6)	C29—C28—C27—C32	3.3 (12)
N3—C5—C6—O2	−123.0 (6)	C28—C27—C32—C31	−2.6 (10)
N3—C5—C6—N2	57.3 (8)	C28—C27—C32—C15	176.7 (7)
N2—C8—C9—C10	104.9 (7)	C30—C31—C32—C27	1.2 (9)
C7—C8—C9—C10	−21.1 (9)	C30—C31—C32—C15	−178.1 (6)
N2—C8—C9—C14	−70.2 (7)	N2—C15—C32—C27	−104.6 (7)
C7—C8—C9—C14	163.8 (7)	C17—C15—C32—C27	28.5 (8)
C10—C9—C14—C13	−2.9 (11)	N2—C15—C32—C31	74.7 (7)
C8—C9—C14—C13	172.5 (8)	C17—C15—C32—C31	−152.2 (5)
C9—C14—C13—C12	1.3 (13)	O1—C18—N1—N1	0.0 (5)
C14—C13—C12—C11	−3.3 (14)	C17—C18—N1—N1	0.0 (6)
C13—C12—C11—C10	6.8 (13)	N1—C18—N1—C19	0(100)
C14—C9—C10—C11	6.7 (12)	O1—C18—N1—C19	−178.6 (5)
C8—C9—C10—C11	−168.4 (7)	C17—C18—N1—C19	4.8 (9)
C12—C11—C10—C9	−8.7 (13)	C20—C19—N1—N1	0.0 (6)
N2—C15—C17—C25	40.5 (8)	C24—C19—N1—N1	0.0 (5)
C32—C15—C17—C25	−90.7 (7)	N1—C19—N1—C18	0(100)
N2—C15—C17—C18	−137.9 (5)	C20—C19—N1—C18	177.9 (6)
C32—C15—C17—C18	90.9 (6)	C24—C19—N1—C18	−2.9 (8)
C25—C17—C18—N1	−3.5 (9)	O2—C6—N2—C8	−162.8 (6)
C15—C17—C18—N1	175.0 (6)	O2—C6—N2—C8	−162.8 (6)
C25—C17—C18—N1	−3.5 (9)	C5—C6—N2—C8	16.9 (8)
C15—C17—C18—N1	175.0 (6)	O2—C6—N2—C15	10.9 (9)
C25—C17—C18—O1	179.7 (5)	O2—C6—N2—C15	10.9 (9)
C15—C17—C18—O1	−1.7 (7)	C5—C6—N2—C15	−169.4 (5)
N1—C19—C20—C21	−179.4 (6)	C9—C8—N2—C6	112.1 (6)
N1—C19—C20—C21	−179.4 (6)	C7—C8—N2—C6	−119.0 (7)
C24—C19—C20—C21	1.3 (10)	C9—C8—N2—C15	−61.8 (7)
C19—C20—C21—C22	0.2 (11)	C7—C8—N2—C15	67.2 (7)
C20—C21—C22—C23	−1.7 (11)	C17—C15—N2—C6	−83.9 (6)
C20—C21—C22—Br1	177.6 (6)	C32—C15—N2—C6	48.9 (7)
C21—C22—C23—C24	1.6 (11)	C17—C15—N2—C8	90.3 (6)
Br1—C22—C23—C24	−177.7 (5)	C32—C15—N2—C8	−137.0 (5)
C22—C23—C24—C25	179.4 (6)	C1—C2—N3—C3	−56.3 (11)
C22—C23—C24—C19	0.0 (9)	C1—C2—N3—C5	179.0 (8)
N1—C19—C24—C23	179.4 (6)	C4—C3—N3—C2	56.6 (10)
N1—C19—C24—C23	179.4 (6)	C4—C3—N3—C5	−179.1 (7)
C20—C19—C24—C23	−1.4 (8)	C6—C5—N3—C2	−177.6 (7)
N1—C19—C24—C25	−0.1 (8)	C6—C5—N3—C3	59.4 (7)
N1—C19—C24—C25	−0.1 (8)	N1—C18—O1—C26	0.0 (9)
C20—C19—C24—C25	179.1 (6)	N1—C18—O1—C26	0.0 (9)
C18—C17—C25—C24	0.1 (8)	C17—C18—O1—C26	176.9 (6)
C15—C17—C25—C24	−178.3 (6)	N2—C6—O2—O2	0.0 (5)
C23—C24—C25—C17	−178.0 (6)	C5—C6—O2—O2	0.0 (5)
C19—C24—C25—C17	1.4 (8)	C2—C1—O3—C4	−57.8 (13)
C32—C31—C30—C29	−0.5 (10)	C3—C4—O3—C1	58.1 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N3	0.98	2.55	3.105 (7)	116
C25—H25···O2	0.93	2.45	3.153 (7)	133
C15—H15···O1	0.98	2.24	2.722 (8)	109
C30—H30···O2i	0.93	2.59	3.399 (10)	145
C7—H7B···Cg4ii	0.96	3.15	3.988 (8)	147
C23—H23···Cg5iii	0.93	2.79	3.662 (8)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N3	0.98	2.55	3.105 (7)	116
C25—H25⋯O2	0.93	2.45	3.153 (7)	133
C30—H30⋯O2i	0.93	2.59	3.399 (10)	145
C7—H7B⋯Cg4ii	0.96	3.15	3.988 (8)	147
C23—H23⋯Cg5iii	0.93	2.79	3.662 (8)	157

Symmetry codes: (i) ; (ii) ; (iii) . Cg4 and Cg5 are the centroids of the O3,C1,C2,N3,C3,C4 and C27–C32 rings, respectively.