Ethyl 8''-chloro-1'-methyl-2,12''-dioxo-12''H-di-spiro-[indoline-3,2'-pyrrolidine- 3',6''-indolo[2,1-b]quinazoline]-4'-carboxyl-ate.

In the title compound, C29H23ClN4O4, the quinazoline-indole system and the indolin-2-one system are each essentially planar, with maximum deviations from their mean planes of 0.150 (2) and 0.072 (2) Å, respectively. The central pyrrolidine ring adopts a twisted conformation on the C-C bond involving the spiro C atoms. Its mean plane forms dihedral angles of 83.37 (9) and 86.56 (8)°, respectively, with the indole rings of the indolin-2-one and quinazoline-indole systems. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked via C-H⋯O hydrogen bonds, forming chains propagating along [001].

Related literature

For quinazoline structures, see: Li & Feng (2009 ▶); Li et al. (2010 ▶); Priya et al. (2011a ▶). For the biological activity of quinazoline derivatives, see: Wolfe et al. (1990 ▶); Tereshima et al. (1995 ▶); Pandeya et al. (1999 ▶); Priya et al. (2011b ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H23ClN4O4

M = 526.96

Triclinic,

a = 8.9341 (9) Å

b = 11.7697 (12) Å

c = 13.3828 (14) Å

α = 72.776 (5)°

β = 89.574 (5)°

γ = 74.995 (5)°

V = 1294.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.945, T max = 0.963

16756 measured reflections

6722 independent reflections

5191 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.161

S = 1.04

6722 reflections

346 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015146/su2600sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015146/su2600Isup2.hkl

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

C29H23ClN4O4	Z = 2
Mr = 526.96	F(000) = 548
Triclinic, P1	Dx = 1.352 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9341 (9) Å	Cell parameters from 6722 reflections
b = 11.7697 (12) Å	θ = 1.6–29.7°
c = 13.3828 (14) Å	µ = 0.19 mm−1
α = 72.776 (5)°	T = 293 K
β = 89.574 (5)°	Block, colourless
γ = 74.995 (5)°	0.30 × 0.25 × 0.20 mm
V = 1294.6 (2) Å3

Bruker SMART APEXII area-detector diffractometer	6722 independent reflections
Radiation source: fine-focus sealed tube	5191 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 29.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.945, Tmax = 0.963	k = −16→16
16756 measured reflections	l = −18→18

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.4319P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
6722 reflections	Δρmax = 0.59 e Å−3
346 parameters	Δρmin = −0.50 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: 0.022 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.0433 (2)	0.42790 (17)	0.28795 (14)	0.0474 (4)
C2	−0.1275 (2)	0.3468 (2)	0.33683 (17)	0.0592 (5)
H2	−0.2181	0.3749	0.3671	0.071*
C3	−0.0777 (2)	0.2237 (2)	0.34100 (18)	0.0587 (5)
H3	−0.1331	0.1679	0.3740	0.070*
C4	0.0570 (2)	0.18699 (16)	0.29445 (13)	0.0429 (4)
C5	0.13927 (18)	0.26916 (15)	0.24246 (12)	0.0364 (3)
C6	0.08974 (19)	0.39168 (15)	0.23894 (13)	0.0411 (4)
H6	0.1439	0.4479	0.2048	0.049*
C7	0.28025 (17)	0.20187 (13)	0.19999 (12)	0.0340 (3)
C8	0.27475 (18)	0.06884 (14)	0.24454 (12)	0.0361 (3)
C9	0.0961 (3)	−0.04311 (19)	0.33813 (18)	0.0591 (5)
C10	0.2124 (3)	−0.15153 (17)	0.32853 (15)	0.0529 (5)
C11	0.3470 (2)	−0.13953 (15)	0.27742 (13)	0.0445 (4)
C12	0.4550 (3)	−0.24456 (18)	0.26869 (17)	0.0568 (5)
H12	0.5443	−0.2371	0.2341	0.068*
C13	0.4304 (3)	−0.3585 (2)	0.3106 (2)	0.0713 (7)
H13	0.5035	−0.4283	0.3049	0.086*
C14	0.2976 (4)	−0.3709 (2)	0.3616 (2)	0.0799 (8)
H14	0.2822	−0.4490	0.3899	0.096*
C15	0.1884 (3)	−0.2690 (2)	0.3706 (2)	0.0730 (7)
H15	0.0989	−0.2779	0.4044	0.088*
C16	0.43389 (18)	0.22977 (15)	0.22466 (14)	0.0402 (3)
H16	0.5202	0.1596	0.2226	0.048*
C17	0.4423 (2)	0.34102 (17)	0.13268 (15)	0.0472 (4)
H17A	0.4313	0.4133	0.1558	0.057*
H17B	0.5408	0.3245	0.1015	0.057*
C18	0.4471 (2)	0.24906 (17)	0.32997 (15)	0.0485 (4)
C19	0.4183 (4)	0.1643 (3)	0.51159 (19)	0.0871 (9)
H19A	0.4540	0.0815	0.5601	0.104*
H19B	0.4909	0.2102	0.5196	0.104*
C20	0.2652 (5)	0.2240 (6)	0.5358 (3)	0.147 (2)
H20A	0.2310	0.3065	0.4886	0.220*
H20B	0.2695	0.2268	0.6067	0.220*
H20C	0.1936	0.1782	0.5281	0.220*
C21	0.3407 (2)	0.41556 (18)	−0.05185 (15)	0.0536 (5)
H21A	0.4363	0.3673	−0.0684	0.080*
H21B	0.3474	0.4983	−0.0619	0.080*
H21C	0.2566	0.4173	−0.0970	0.080*
C22	0.27177 (17)	0.24447 (13)	0.07722 (12)	0.0336 (3)
C23	0.38921 (18)	0.14670 (14)	0.03777 (13)	0.0387 (3)
C24	0.12036 (17)	0.24951 (14)	0.02419 (12)	0.0353 (3)
C25	−0.02790 (19)	0.32460 (17)	0.01850 (14)	0.0446 (4)
H25	−0.0480	0.3877	0.0493	0.054*
C26	−0.1467 (2)	0.3041 (2)	−0.03426 (17)	0.0563 (5)
H26	−0.2474	0.3541	−0.0387	0.068*
C27	−0.1176 (2)	0.2107 (2)	−0.08016 (17)	0.0598 (5)
H27	−0.1995	0.1973	−0.1134	0.072*
C28	0.0317 (2)	0.13666 (18)	−0.07758 (16)	0.0526 (4)
H28	0.0520	0.0748	−0.1097	0.063*
C29	0.14840 (19)	0.15821 (15)	−0.02564 (13)	0.0397 (3)
N1	0.37705 (16)	−0.02506 (12)	0.23485 (11)	0.0415 (3)
N2	0.13797 (17)	0.06638 (13)	0.29362 (12)	0.0436 (3)
N3	0.31307 (16)	0.36062 (12)	0.05689 (11)	0.0391 (3)
N4	0.30806 (16)	0.10001 (13)	−0.01648 (12)	0.0442 (3)
H4	0.3491	0.0415	−0.0425	0.053*
O1	−0.0250 (3)	−0.04254 (17)	0.37966 (19)	0.0995 (7)
O2	0.4841 (2)	0.33332 (18)	0.34553 (14)	0.0815 (5)
O3	0.4134 (2)	0.15839 (14)	0.40408 (11)	0.0665 (4)
O4	0.53071 (13)	0.12214 (12)	0.05120 (11)	0.0489 (3)
Cl1	−0.10529 (7)	0.58059 (5)	0.28817 (5)	0.0708 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0454 (9)	0.0461 (10)	0.0500 (9)	−0.0007 (7)	0.0045 (7)	−0.0236 (8)
C2	0.0483 (10)	0.0634 (13)	0.0642 (12)	−0.0046 (9)	0.0200 (9)	−0.0265 (10)
C3	0.0527 (11)	0.0557 (11)	0.0689 (12)	−0.0159 (9)	0.0245 (9)	−0.0201 (9)
C4	0.0429 (9)	0.0403 (9)	0.0457 (9)	−0.0095 (7)	0.0066 (7)	−0.0149 (7)
C5	0.0353 (7)	0.0385 (8)	0.0375 (7)	−0.0075 (6)	0.0037 (6)	−0.0165 (6)
C6	0.0409 (8)	0.0396 (8)	0.0444 (8)	−0.0061 (7)	0.0052 (6)	−0.0192 (7)
C7	0.0311 (7)	0.0305 (7)	0.0425 (8)	−0.0064 (6)	0.0032 (6)	−0.0159 (6)
C8	0.0373 (7)	0.0334 (8)	0.0384 (7)	−0.0089 (6)	−0.0011 (6)	−0.0126 (6)
C9	0.0665 (12)	0.0476 (11)	0.0668 (13)	−0.0257 (9)	0.0176 (10)	−0.0143 (9)
C10	0.0693 (12)	0.0378 (9)	0.0529 (10)	−0.0189 (8)	−0.0002 (9)	−0.0120 (7)
C11	0.0527 (10)	0.0350 (8)	0.0450 (9)	−0.0100 (7)	−0.0102 (7)	−0.0124 (7)
C12	0.0604 (11)	0.0400 (10)	0.0674 (12)	−0.0052 (8)	−0.0116 (9)	−0.0190 (8)
C13	0.0839 (16)	0.0370 (10)	0.0862 (16)	−0.0048 (10)	−0.0139 (13)	−0.0183 (10)
C14	0.111 (2)	0.0353 (11)	0.0895 (17)	−0.0228 (12)	−0.0025 (15)	−0.0101 (10)
C15	0.0948 (18)	0.0485 (12)	0.0788 (15)	−0.0326 (12)	0.0131 (13)	−0.0128 (10)
C16	0.0326 (7)	0.0389 (8)	0.0545 (9)	−0.0075 (6)	0.0012 (6)	−0.0238 (7)
C17	0.0425 (9)	0.0467 (9)	0.0632 (11)	−0.0206 (7)	0.0100 (8)	−0.0253 (8)
C18	0.0416 (9)	0.0480 (10)	0.0598 (11)	−0.0068 (7)	−0.0062 (7)	−0.0264 (8)
C19	0.121 (2)	0.0858 (18)	0.0492 (12)	−0.0113 (16)	−0.0141 (13)	−0.0274 (12)
C20	0.112 (3)	0.275 (6)	0.101 (3)	−0.081 (4)	0.033 (2)	−0.102 (3)
C21	0.0618 (11)	0.0452 (10)	0.0564 (11)	−0.0203 (9)	0.0184 (9)	−0.0143 (8)
C22	0.0305 (7)	0.0305 (7)	0.0419 (8)	−0.0063 (5)	0.0063 (5)	−0.0160 (6)
C23	0.0360 (8)	0.0351 (8)	0.0468 (8)	−0.0059 (6)	0.0074 (6)	−0.0186 (6)
C24	0.0336 (7)	0.0335 (7)	0.0383 (7)	−0.0068 (6)	0.0029 (6)	−0.0122 (6)
C25	0.0372 (8)	0.0463 (9)	0.0495 (9)	−0.0040 (7)	0.0027 (7)	−0.0197 (7)
C26	0.0345 (8)	0.0670 (13)	0.0640 (12)	−0.0025 (8)	−0.0044 (8)	−0.0244 (10)
C27	0.0472 (10)	0.0687 (13)	0.0668 (12)	−0.0156 (9)	−0.0106 (9)	−0.0255 (10)
C28	0.0538 (10)	0.0503 (10)	0.0594 (11)	−0.0121 (8)	−0.0059 (8)	−0.0268 (8)
C29	0.0401 (8)	0.0360 (8)	0.0429 (8)	−0.0072 (6)	0.0003 (6)	−0.0144 (6)
N1	0.0417 (7)	0.0338 (7)	0.0487 (8)	−0.0065 (6)	−0.0035 (6)	−0.0152 (6)
N2	0.0445 (8)	0.0369 (7)	0.0501 (8)	−0.0116 (6)	0.0087 (6)	−0.0139 (6)
N3	0.0389 (7)	0.0335 (7)	0.0485 (7)	−0.0120 (5)	0.0104 (5)	−0.0161 (5)
N4	0.0410 (7)	0.0406 (8)	0.0554 (8)	−0.0021 (6)	0.0024 (6)	−0.0287 (6)
O1	0.0973 (14)	0.0625 (11)	0.1478 (19)	−0.0391 (10)	0.0673 (13)	−0.0317 (11)
O2	0.1052 (14)	0.0883 (12)	0.0827 (11)	−0.0511 (11)	0.0076 (10)	−0.0514 (10)
O3	0.0946 (12)	0.0566 (9)	0.0479 (8)	−0.0149 (8)	−0.0109 (7)	−0.0195 (6)
O4	0.0335 (6)	0.0490 (7)	0.0715 (8)	−0.0064 (5)	0.0110 (5)	−0.0337 (6)
Cl1	0.0664 (3)	0.0550 (3)	0.0940 (4)	0.0023 (2)	0.0119 (3)	−0.0436 (3)

C1—C2	1.378 (3)	C17—N3	1.468 (2)
C1—C6	1.384 (2)	C17—H17A	0.9700
C1—Cl1	1.7390 (19)	C17—H17B	0.9700
C2—C3	1.385 (3)	C18—O2	1.195 (2)
C2—H2	0.9300	C18—O3	1.322 (2)
C3—C4	1.379 (3)	C19—C20	1.449 (5)
C3—H3	0.9300	C19—O3	1.462 (3)
C4—C5	1.386 (2)	C19—H19A	0.9700
C4—N2	1.420 (2)	C19—H19B	0.9700
C5—C6	1.381 (2)	C20—H20A	0.9600
C5—C7	1.509 (2)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600
C7—C8	1.515 (2)	C21—N3	1.455 (2)
C7—C16	1.551 (2)	C21—H21A	0.9600
C7—C22	1.566 (2)	C21—H21B	0.9600
C8—N1	1.278 (2)	C21—H21C	0.9600
C8—N2	1.386 (2)	C22—N3	1.4555 (19)
C9—O1	1.212 (3)	C22—C24	1.512 (2)
C9—N2	1.395 (2)	C22—C23	1.559 (2)
C9—C10	1.460 (3)	C23—O4	1.2237 (19)
C10—C11	1.398 (3)	C23—N4	1.344 (2)
C10—C15	1.402 (3)	C24—C25	1.377 (2)
C11—C12	1.392 (3)	C24—C29	1.395 (2)
C11—N1	1.394 (2)	C25—C26	1.388 (3)
C12—C13	1.367 (3)	C25—H25	0.9300
C12—H12	0.9300	C26—C27	1.379 (3)
C13—C14	1.383 (4)	C26—H26	0.9300
C13—H13	0.9300	C27—C28	1.386 (3)
C14—C15	1.372 (4)	C27—H27	0.9300
C14—H14	0.9300	C28—C29	1.374 (2)
C15—H15	0.9300	C28—H28	0.9300
C16—C18	1.503 (2)	C29—N4	1.402 (2)
C16—C17	1.527 (2)	N4—H4	0.8600
C16—H16	0.9800
C2—C1—C6	122.13 (17)	O2—C18—O3	124.37 (19)
C2—C1—Cl1	119.09 (14)	O2—C18—C16	125.3 (2)
C6—C1—Cl1	118.78 (15)	O3—C18—C16	110.28 (15)
C1—C2—C3	120.27 (17)	C20—C19—O3	110.2 (2)
C1—C2—H2	119.9	C20—C19—H19A	109.6
C3—C2—H2	119.9	O3—C19—H19A	109.6
C4—C3—C2	117.58 (18)	C20—C19—H19B	109.6
C4—C3—H3	121.2	O3—C19—H19B	109.6
C2—C3—H3	121.2	H19A—C19—H19B	108.1
C3—C4—C5	122.23 (17)	C19—C20—H20A	109.5
C3—C4—N2	128.84 (17)	C19—C20—H20B	109.5
C5—C4—N2	108.87 (14)	H20A—C20—H20B	109.5
C6—C5—C4	120.00 (15)	C19—C20—H20C	109.5
C6—C5—C7	130.09 (14)	H20A—C20—H20C	109.5
C4—C5—C7	109.87 (14)	H20B—C20—H20C	109.5
C5—C6—C1	117.73 (16)	N3—C21—H21A	109.5
C5—C6—H6	121.1	N3—C21—H21B	109.5
C1—C6—H6	121.1	H21A—C21—H21B	109.5
C5—C7—C8	101.82 (12)	N3—C21—H21C	109.5
C5—C7—C16	114.53 (12)	H21A—C21—H21C	109.5
C8—C7—C16	116.11 (12)	H21B—C21—H21C	109.5
C5—C7—C22	112.56 (12)	N3—C22—C24	116.72 (13)
C8—C7—C22	111.93 (12)	N3—C22—C23	113.52 (12)
C16—C7—C22	100.39 (12)	C24—C22—C23	101.29 (12)
N1—C8—N2	125.77 (15)	N3—C22—C7	100.51 (11)
N1—C8—C7	125.36 (14)	C24—C22—C7	115.11 (12)
N2—C8—C7	108.82 (13)	C23—C22—C7	110.10 (12)
O1—C9—N2	121.0 (2)	O4—C23—N4	126.97 (15)
O1—C9—C10	126.37 (19)	O4—C23—C22	124.83 (14)
N2—C9—C10	112.66 (17)	N4—C23—C22	108.14 (13)
C11—C10—C15	119.5 (2)	C25—C24—C29	119.60 (15)
C11—C10—C9	120.78 (16)	C25—C24—C22	131.85 (15)
C15—C10—C9	119.7 (2)	C29—C24—C22	108.54 (13)
C12—C11—N1	118.71 (18)	C24—C25—C26	118.58 (17)
C12—C11—C10	119.41 (17)	C24—C25—H25	120.7
N1—C11—C10	121.88 (16)	C26—C25—H25	120.7
C13—C12—C11	120.3 (2)	C27—C26—C25	120.98 (17)
C13—C12—H12	119.8	C27—C26—H26	119.5
C11—C12—H12	119.8	C25—C26—H26	119.5
C12—C13—C14	120.5 (2)	C26—C27—C28	121.07 (17)
C12—C13—H13	119.8	C26—C27—H27	119.5
C14—C13—H13	119.8	C28—C27—H27	119.5
C15—C14—C13	120.5 (2)	C29—C28—C27	117.41 (18)
C15—C14—H14	119.7	C29—C28—H28	121.3
C13—C14—H14	119.7	C27—C28—H28	121.3
C14—C15—C10	119.7 (2)	C28—C29—C24	122.30 (16)
C14—C15—H15	120.2	C28—C29—N4	127.95 (16)
C10—C15—H15	120.2	C24—C29—N4	109.72 (14)
C18—C16—C17	113.67 (14)	C8—N1—C11	116.60 (15)
C18—C16—C7	114.51 (14)	C8—N2—C9	122.30 (15)
C17—C16—C7	104.53 (13)	C8—N2—C4	110.19 (13)
C18—C16—H16	107.9	C9—N2—C4	127.47 (16)
C17—C16—H16	107.9	C21—N3—C22	114.39 (13)
C7—C16—H16	107.9	C21—N3—C17	114.30 (14)
N3—C17—C16	105.79 (12)	C22—N3—C17	107.73 (13)
N3—C17—H17A	110.6	C23—N4—C29	111.88 (13)
C16—C17—H17A	110.6	C23—N4—H4	124.1
N3—C17—H17B	110.6	C29—N4—H4	124.1
C16—C17—H17B	110.6	C18—O3—C19	117.25 (19)
H17A—C17—H17B	108.7
C6—C1—C2—C3	2.0 (3)	C5—C7—C22—C23	−162.07 (12)
Cl1—C1—C2—C3	−177.74 (17)	C8—C7—C22—C23	−48.09 (16)
C1—C2—C3—C4	−0.3 (3)	C16—C7—C22—C23	75.70 (14)
C2—C3—C4—C5	−1.7 (3)	N3—C22—C23—O4	45.3 (2)
C2—C3—C4—N2	175.36 (19)	C24—C22—C23—O4	171.30 (16)
C3—C4—C5—C6	2.1 (3)	C7—C22—C23—O4	−66.4 (2)
N2—C4—C5—C6	−175.50 (14)	N3—C22—C23—N4	−131.88 (14)
C3—C4—C5—C7	−179.89 (17)	C24—C22—C23—N4	−5.93 (16)
N2—C4—C5—C7	2.50 (19)	C7—C22—C23—N4	116.34 (14)
C4—C5—C6—C1	−0.4 (2)	N3—C22—C24—C25	−50.0 (2)
C7—C5—C6—C1	−177.96 (16)	C23—C22—C24—C25	−173.76 (17)
C2—C1—C6—C5	−1.6 (3)	C7—C22—C24—C25	67.5 (2)
Cl1—C1—C6—C5	178.12 (12)	N3—C22—C24—C29	129.99 (14)
C6—C5—C7—C8	172.28 (16)	C23—C22—C24—C29	6.19 (16)
C4—C5—C7—C8	−5.45 (16)	C7—C22—C24—C29	−112.53 (15)
C6—C5—C7—C16	46.1 (2)	C29—C24—C25—C26	2.1 (3)
C4—C5—C7—C16	−131.60 (15)	C22—C24—C25—C26	−177.94 (17)
C6—C5—C7—C22	−67.7 (2)	C24—C25—C26—C27	0.0 (3)
C4—C5—C7—C22	114.56 (15)	C25—C26—C27—C28	−1.8 (4)
C5—C7—C8—N1	−175.82 (15)	C26—C27—C28—C29	1.4 (3)
C16—C7—C8—N1	−50.7 (2)	C27—C28—C29—C24	0.8 (3)
C22—C7—C8—N1	63.73 (19)	C27—C28—C29—N4	−176.79 (19)
C5—C7—C8—N2	6.56 (16)	C25—C24—C29—C28	−2.5 (3)
C16—C7—C8—N2	131.66 (14)	C22—C24—C29—C28	177.49 (16)
C22—C7—C8—N2	−113.89 (14)	C25—C24—C29—N4	175.40 (15)
O1—C9—C10—C11	179.2 (2)	C22—C24—C29—N4	−4.56 (19)
N2—C9—C10—C11	−1.1 (3)	N2—C8—N1—C11	0.2 (2)
O1—C9—C10—C15	−0.5 (4)	C7—C8—N1—C11	−177.04 (14)
N2—C9—C10—C15	179.20 (19)	C12—C11—N1—C8	179.91 (15)
C15—C10—C11—C12	0.3 (3)	C10—C11—N1—C8	−0.2 (2)
C9—C10—C11—C12	−179.39 (18)	N1—C8—N2—C9	−0.7 (3)
C15—C10—C11—N1	−179.57 (18)	C7—C8—N2—C9	176.92 (16)
C9—C10—C11—N1	0.8 (3)	N1—C8—N2—C4	176.85 (15)
N1—C11—C12—C13	179.18 (18)	C7—C8—N2—C4	−5.54 (18)
C10—C11—C12—C13	−0.7 (3)	O1—C9—N2—C8	−179.2 (2)
C11—C12—C13—C14	0.5 (4)	C10—C9—N2—C8	1.1 (3)
C12—C13—C14—C15	0.1 (4)	O1—C9—N2—C4	3.7 (4)
C13—C14—C15—C10	−0.5 (4)	C10—C9—N2—C4	−176.00 (17)
C11—C10—C15—C14	0.3 (4)	C3—C4—N2—C8	−175.45 (19)
C9—C10—C15—C14	180.0 (2)	C5—C4—N2—C8	1.95 (19)
C5—C7—C16—C18	35.44 (19)	C3—C4—N2—C9	1.9 (3)
C8—C7—C16—C18	−82.88 (17)	C5—C4—N2—C9	179.32 (18)
C22—C7—C16—C18	156.27 (14)	C24—C22—N3—C21	−64.33 (18)
C5—C7—C16—C17	−89.58 (16)	C23—C22—N3—C21	52.94 (19)
C8—C7—C16—C17	152.10 (14)	C7—C22—N3—C21	170.46 (13)
C22—C7—C16—C17	31.25 (15)	C24—C22—N3—C17	167.41 (13)
C18—C16—C17—N3	−132.70 (14)	C23—C22—N3—C17	−75.32 (16)
C7—C16—C17—N3	−7.14 (17)	C7—C22—N3—C17	42.19 (15)
C17—C16—C18—O2	−11.0 (3)	C16—C17—N3—C21	−150.84 (14)
C7—C16—C18—O2	−131.0 (2)	C16—C17—N3—C22	−22.53 (17)
C17—C16—C18—O3	169.66 (15)	O4—C23—N4—C29	−173.51 (17)
C7—C16—C18—O3	49.6 (2)	C22—C23—N4—C29	3.64 (19)
C5—C7—C22—N3	77.92 (14)	C28—C29—N4—C23	178.30 (18)
C8—C7—C22—N3	−168.10 (12)	C24—C29—N4—C23	0.5 (2)
C16—C7—C22—N3	−44.31 (13)	O2—C18—O3—C19	1.6 (3)
C5—C7—C22—C24	−48.38 (17)	C16—C18—O3—C19	−179.00 (19)
C8—C7—C22—C24	65.60 (16)	C20—C19—O3—C18	93.5 (4)
C16—C7—C22—C24	−170.61 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O4i	0.86	1.98	2.808 (2)	160
C20—H20C···O1ii	0.96	2.53	3.369 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O4i	0.86	1.98	2.808 (2)	160
C20—H20C⋯O1ii	0.96	2.53	3.369 (6)	146

Symmetry codes: (i) ; (ii) .