Ethyl 3-(4-chloro-phen-yl)-2-(dipentyl-amino)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo-[3,2-d]pyrimidine-7-carboxyl-ate.

In the title compound, C(31)H(37)ClN(4)O(3), the fused rings of the pyrrolo-[3,2-d]pyrimidine system form a dihedral angle of 5.80 (11)°. The phenyl and benzene rings are twisted with respect to the mean plane of the pyrrolo-[3,2-d]pyrimidine system [maximum deviation = 0.077 (2) Å], making dihedral angles of 61.05 (12) and 75.39 (10)°, respectively. The eth-oxy group is disordered over two positions with the site-occupancy ratio fixed at 0.54:0.46. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to the ab plane. There are also π-π [centroid-centroid distances = 3.5954 (17) and 3.965 (2) Å] and C-H⋯π inter-actions present.

Related literature

The title compound may be used as a precursor for obtaining bioactive mol­ecules, see: Otmar et al. (2004 ▶). For the biological activity of pyrrolo­pyrimidine derivatives, see: Pudziuvelyte et al. (2009 ▶); Kamath et al. (2009 ▶). For related structures, see: He et al. (2007a ▶,b ▶).

Experimental

Crystal data

C31H37ClN4O3

M = 549.10

Triclinic,

a = 9.661 (3) Å

b = 12.422 (4) Å

c = 14.007 (4) Å

α = 72.110 (5)°

β = 82.697 (6)°

γ = 70.184 (5)°

V = 1504.4 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 298 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.943, T max = 0.984

9954 measured reflections

5241 independent reflections

3801 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.182

S = 1.09

5241 reflections

386 parameters

42 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024609/su2435sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024609/su2435Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024609/su2435Isup3.cml

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

C31H37ClN4O3	Z = 2
Mr = 549.10	F(000) = 584
Triclinic, P1	Dx = 1.212 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.661 (3) Å	Cell parameters from 3181 reflections
b = 12.422 (4) Å	θ = 2.4–26.4°
c = 14.007 (4) Å	µ = 0.16 mm−1
α = 72.110 (5)°	T = 298 K
β = 82.697 (6)°	Block, colourless
γ = 70.184 (5)°	0.30 × 0.10 × 0.10 mm
V = 1504.4 (8) Å3

Bruker APEXII CCD diffractometer	5241 independent reflections
Radiation source: fine-focus sealed tube	3801 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→10
Tmin = 0.943, Tmax = 0.984	k = −14→14
9954 measured reflections	l = −16→16

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.1048P)2 + 0.1603P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
5241 reflections	Δρmax = 0.35 e Å−3
386 parameters	Δρmin = −0.26 e Å−3
42 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

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	Occ. (<1)
C1	0.5649 (3)	−0.2757 (2)	0.17362 (19)	0.0605 (7)
C2	0.5823 (3)	−0.2786 (2)	0.27016 (19)	0.0621 (7)
H2	0.6727	−0.3194	0.3008	0.075*
C3	0.4628 (3)	−0.2197 (2)	0.32125 (18)	0.0535 (6)
H3	0.4721	−0.2216	0.3871	0.064*
C4	0.3302 (2)	−0.15846 (19)	0.27457 (16)	0.0427 (5)
C5	0.3144 (3)	−0.1581 (2)	0.17863 (18)	0.0562 (6)
H5	0.2240	−0.1178	0.1479	0.067*
C6	0.4326 (3)	−0.2176 (3)	0.1273 (2)	0.0647 (7)
H6	0.4223	−0.2181	0.0623	0.078*
C7	0.1369 (2)	0.02435 (19)	0.29938 (16)	0.0423 (5)
C8	−0.0692 (2)	0.00511 (18)	0.39051 (15)	0.0381 (5)
C9	−0.0072 (2)	−0.11672 (18)	0.42804 (15)	0.0390 (5)
C10	0.1361 (2)	−0.17963 (19)	0.39785 (16)	0.0433 (5)
C11	0.3656 (3)	0.0775 (2)	0.25637 (19)	0.0551 (6)
H11A	0.3991	0.0072	0.3128	0.066*
H11B	0.3620	0.1463	0.2768	0.066*
C12	0.4759 (3)	0.0666 (3)	0.1695 (2)	0.0673 (7)
H12A	0.4629	0.0104	0.1390	0.081*
H12B	0.4550	0.1435	0.1192	0.081*
C13	0.6346 (3)	0.0259 (3)	0.1994 (2)	0.0791 (9)
H13A	0.6489	−0.0405	0.2600	0.095*
H13B	0.6529	0.0905	0.2154	0.095*
C14	0.7479 (3)	−0.0127 (4)	0.1196 (3)	0.0934 (11)
H14A	0.7158	−0.0627	0.0920	0.112*
H14B	0.7497	0.0578	0.0655	0.112*
C15	0.8970 (4)	−0.0774 (4)	0.1548 (3)	0.1099 (13)
H15A	0.9267	−0.0326	0.1886	0.165*
H15B	0.9627	−0.0886	0.0986	0.165*
H15C	0.9000	−0.1537	0.2004	0.165*
C16	0.1306 (3)	0.2113 (2)	0.1768 (2)	0.0593 (7)
H16A	0.1981	0.2542	0.1420	0.071*
H16B	0.0733	0.2519	0.2249	0.071*
C17	0.0288 (4)	0.2168 (3)	0.1022 (2)	0.0765 (8)
H17A	−0.0349	0.1701	0.1364	0.092*
H17B	0.0868	0.1799	0.0520	0.092*
C18	−0.0650 (4)	0.3403 (3)	0.0502 (3)	0.0929 (11)
H18A	−0.0011	0.3863	0.0149	0.111*
H18B	−0.1211	0.3776	0.1006	0.111*
C19	−0.1715 (7)	0.3471 (4)	−0.0243 (4)	0.157 (2)
H19A	−0.1143	0.3089	−0.0740	0.189*
H19B	−0.2340	0.3000	0.0115	0.189*
C20	−0.2658 (8)	0.4638 (5)	−0.0773 (5)	0.187 (3)
H20A	−0.3324	0.4994	−0.0303	0.281*
H20B	−0.3209	0.4558	−0.1257	0.281*
H20C	−0.2067	0.5134	−0.1110	0.281*
C21	−0.2389 (2)	−0.07124 (19)	0.48391 (16)	0.0441 (5)
H21	−0.3270	−0.0786	0.5160	0.053*
C22	−0.0964 (2)	−0.28502 (19)	0.53985 (16)	0.0436 (5)
C23	−0.1896 (3)	−0.3390 (2)	0.5213 (2)	0.0607 (7)
H23	−0.2614	−0.2964	0.4732	0.073*
C24	−0.1771 (4)	−0.4547 (3)	0.5732 (3)	0.0774 (9)
H24	−0.2385	−0.4917	0.5598	0.093*
C25	−0.0728 (4)	−0.5153 (3)	0.6453 (3)	0.0847 (11)
H25	−0.0638	−0.5939	0.6813	0.102*
C26	0.0186 (4)	−0.4612 (3)	0.6650 (2)	0.0757 (8)
H26	0.0882	−0.5031	0.7146	0.091*
C27	0.0080 (3)	−0.3454 (2)	0.61195 (18)	0.0564 (6)
H27	0.0705	−0.3089	0.6247	0.068*
C28	−0.3371 (3)	0.1472 (2)	0.41352 (18)	0.0513 (6)
O2	−0.3074 (8)	0.2389 (6)	0.3374 (4)	0.0579 (16)	0.54
C29	−0.4238 (12)	0.3582 (9)	0.3102 (8)	0.106 (3)	0.54
H29A	−0.5180	0.3480	0.3066	0.127*	0.54
H29B	−0.4004	0.4054	0.2448	0.127*	0.54
C30	−0.4335 (10)	0.4226 (8)	0.3879 (7)	0.128 (3)	0.54
H30A	−0.4741	0.3836	0.4497	0.193*	0.54
H30B	−0.4957	0.5038	0.3643	0.193*	0.54
H30C	−0.3369	0.4213	0.3991	0.193*	0.54
O2'	−0.2896 (9)	0.2395 (7)	0.3724 (5)	0.0584 (18)	0.46
C29'	−0.4027 (9)	0.3551 (6)	0.3531 (7)	0.070 (2)	0.46
H29C	−0.3579	0.4150	0.3506	0.084*	0.46
H29D	−0.4738	0.3540	0.4087	0.084*	0.46
C30'	−0.4826 (14)	0.3907 (12)	0.2571 (9)	0.147 (5)	0.46
H30D	−0.4127	0.3869	0.2021	0.220*	0.46
H30E	−0.5492	0.4707	0.2461	0.220*	0.46
H30F	−0.5371	0.3373	0.2620	0.220*	0.46
C31	−0.2180 (2)	0.03478 (19)	0.42781 (16)	0.0411 (5)
Cl1	0.71506 (9)	−0.34780 (9)	0.10790 (6)	0.1034 (4)
N1	0.20328 (18)	−0.09956 (15)	0.32853 (13)	0.0417 (4)
N2	0.00551 (19)	0.07781 (15)	0.32903 (13)	0.0431 (4)
N3	−0.11308 (19)	−0.16311 (15)	0.48561 (13)	0.0413 (4)
N4	0.2161 (2)	0.09019 (17)	0.23112 (15)	0.0512 (5)
O1	0.19808 (19)	−0.28622 (14)	0.41939 (15)	0.0648 (5)
O3	−0.45802 (18)	0.15757 (16)	0.45300 (16)	0.0703 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0476 (14)	0.0637 (15)	0.0541 (15)	−0.0005 (12)	0.0113 (12)	−0.0183 (12)
C2	0.0411 (13)	0.0717 (17)	0.0558 (15)	0.0019 (12)	−0.0012 (11)	−0.0154 (13)
C3	0.0415 (13)	0.0670 (15)	0.0436 (13)	−0.0068 (11)	0.0010 (10)	−0.0163 (11)
C4	0.0345 (11)	0.0458 (12)	0.0445 (12)	−0.0110 (9)	0.0078 (9)	−0.0135 (9)
C5	0.0399 (13)	0.0698 (16)	0.0522 (14)	−0.0059 (12)	−0.0021 (11)	−0.0203 (12)
C6	0.0595 (16)	0.0802 (18)	0.0487 (14)	−0.0088 (14)	0.0040 (12)	−0.0276 (13)
C7	0.0392 (12)	0.0435 (12)	0.0435 (12)	−0.0148 (10)	0.0068 (9)	−0.0126 (10)
C8	0.0326 (11)	0.0432 (11)	0.0381 (11)	−0.0124 (9)	0.0029 (9)	−0.0120 (9)
C9	0.0357 (11)	0.0428 (11)	0.0403 (11)	−0.0149 (9)	0.0054 (9)	−0.0141 (9)
C10	0.0375 (12)	0.0421 (12)	0.0500 (13)	−0.0132 (10)	0.0081 (10)	−0.0158 (10)
C11	0.0529 (14)	0.0643 (15)	0.0544 (14)	−0.0298 (12)	0.0105 (11)	−0.0178 (12)
C12	0.0478 (15)	0.098 (2)	0.0561 (15)	−0.0347 (15)	0.0102 (12)	−0.0143 (14)
C13	0.0550 (17)	0.114 (3)	0.0741 (19)	−0.0374 (17)	0.0087 (14)	−0.0274 (18)
C14	0.0560 (19)	0.139 (3)	0.086 (2)	−0.035 (2)	0.0066 (16)	−0.032 (2)
C15	0.067 (2)	0.131 (3)	0.130 (3)	−0.013 (2)	−0.009 (2)	−0.052 (3)
C16	0.0582 (15)	0.0456 (13)	0.0661 (16)	−0.0190 (11)	0.0189 (13)	−0.0103 (12)
C17	0.093 (2)	0.0589 (16)	0.0670 (18)	−0.0211 (16)	0.0017 (16)	−0.0077 (14)
C18	0.084 (2)	0.076 (2)	0.089 (2)	−0.0084 (18)	0.0040 (19)	−0.0038 (18)
C19	0.205 (6)	0.094 (3)	0.153 (4)	−0.018 (3)	−0.092 (5)	−0.007 (3)
C20	0.201 (7)	0.140 (5)	0.179 (6)	0.001 (5)	−0.075 (5)	−0.021 (4)
C21	0.0331 (11)	0.0511 (13)	0.0473 (12)	−0.0131 (10)	0.0070 (9)	−0.0164 (10)
C22	0.0409 (12)	0.0422 (12)	0.0459 (12)	−0.0146 (10)	0.0126 (10)	−0.0137 (10)
C23	0.0484 (14)	0.0561 (15)	0.0821 (18)	−0.0209 (12)	0.0093 (13)	−0.0254 (14)
C24	0.0684 (19)	0.0572 (17)	0.113 (3)	−0.0324 (15)	0.0261 (19)	−0.0305 (18)
C25	0.095 (3)	0.0448 (15)	0.098 (2)	−0.0232 (17)	0.041 (2)	−0.0140 (16)
C26	0.077 (2)	0.0582 (16)	0.0685 (18)	−0.0071 (15)	0.0071 (15)	−0.0047 (14)
C27	0.0552 (15)	0.0511 (14)	0.0564 (15)	−0.0133 (12)	0.0000 (12)	−0.0108 (12)
C28	0.0393 (13)	0.0509 (13)	0.0595 (14)	−0.0110 (10)	0.0029 (11)	−0.0154 (11)
O2	0.048 (2)	0.045 (2)	0.057 (3)	0.0009 (17)	0.004 (2)	0.000 (2)
C29	0.099 (5)	0.114 (5)	0.090 (5)	−0.017 (4)	0.005 (4)	−0.032 (4)
C30	0.113 (5)	0.118 (4)	0.155 (5)	−0.047 (4)	0.000 (4)	−0.030 (4)
O2'	0.050 (3)	0.047 (3)	0.067 (4)	−0.009 (2)	−0.001 (3)	−0.009 (3)
C29'	0.070 (4)	0.045 (3)	0.083 (4)	−0.003 (3)	0.004 (3)	−0.020 (3)
C30'	0.136 (6)	0.146 (6)	0.138 (6)	−0.034 (4)	−0.012 (4)	−0.020 (4)
C31	0.0333 (11)	0.0461 (12)	0.0425 (12)	−0.0104 (9)	0.0030 (9)	−0.0145 (10)
Cl1	0.0746 (6)	0.1193 (7)	0.0770 (6)	0.0211 (5)	0.0203 (4)	−0.0398 (5)
N1	0.0322 (9)	0.0423 (10)	0.0477 (10)	−0.0110 (8)	0.0104 (8)	−0.0143 (8)
N2	0.0383 (10)	0.0431 (10)	0.0475 (10)	−0.0141 (8)	0.0073 (8)	−0.0144 (8)
N3	0.0349 (10)	0.0448 (10)	0.0446 (10)	−0.0155 (8)	0.0069 (8)	−0.0130 (8)
N4	0.0424 (11)	0.0473 (11)	0.0584 (12)	−0.0172 (9)	0.0126 (9)	−0.0096 (9)
O1	0.0516 (10)	0.0408 (9)	0.0872 (13)	−0.0099 (8)	0.0225 (9)	−0.0123 (8)
O3	0.0378 (10)	0.0626 (11)	0.0981 (14)	−0.0077 (8)	0.0183 (9)	−0.0224 (10)

C1—C6	1.369 (4)	C17—H17B	0.9700
C1—C2	1.372 (4)	C18—C19	1.520 (6)
C1—Cl1	1.743 (2)	C18—H18A	0.9700
C2—C3	1.386 (3)	C18—H18B	0.9700
C2—H2	0.9300	C19—C20	1.448 (6)
C3—C4	1.376 (3)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.370 (3)	C20—H20A	0.9600
C4—N1	1.451 (3)	C20—H20B	0.9600
C5—C6	1.382 (3)	C20—H20C	0.9600
C5—H5	0.9300	C21—N3	1.353 (3)
C6—H6	0.9300	C21—C31	1.377 (3)
C7—N2	1.300 (3)	C21—H21	0.9300
C7—N4	1.388 (3)	C22—C27	1.372 (3)
C7—N1	1.399 (3)	C22—C23	1.380 (3)
C8—N2	1.373 (3)	C22—N3	1.434 (3)
C8—C9	1.379 (3)	C23—C24	1.368 (4)
C8—C31	1.429 (3)	C23—H23	0.9300
C9—N3	1.390 (3)	C24—C25	1.371 (5)
C9—C10	1.423 (3)	C24—H24	0.9300
C10—O1	1.211 (3)	C25—C26	1.374 (5)
C10—N1	1.428 (3)	C25—H25	0.9300
C11—N4	1.476 (3)	C26—C27	1.376 (4)
C11—C12	1.519 (3)	C26—H26	0.9300
C11—H11A	0.9700	C27—H27	0.9300
C11—H11B	0.9700	C28—O3	1.210 (3)
C12—C13	1.513 (4)	C28—O2'	1.319 (9)
C12—H12A	0.9700	C28—O2	1.383 (7)
C12—H12B	0.9700	C28—C31	1.453 (3)
C13—C14	1.531 (4)	O2—C29	1.496 (10)
C13—H13A	0.9700	C29—C30	1.514 (8)
C13—H13B	0.9700	C29—H29A	0.9700
C14—C15	1.454 (5)	C29—H29B	0.9700
C14—H14A	0.9700	C30—H30A	0.9600
C14—H14B	0.9700	C30—H30B	0.9600
C15—H15A	0.9600	C30—H30C	0.9600
C15—H15B	0.9600	O2'—C29'	1.450 (9)
C15—H15C	0.9600	C29'—C30'	1.505 (9)
C16—N4	1.463 (3)	C29'—H29C	0.9700
C16—C17	1.495 (4)	C29'—H29D	0.9700
C16—H16A	0.9700	C30'—H30D	0.9600
C16—H16B	0.9700	C30'—H30E	0.9600
C17—C18	1.499 (4)	C30'—H30F	0.9600
C17—H17A	0.9700
C6—C1—C2	121.7 (2)	C17—C18—H18B	108.5
C6—C1—Cl1	119.0 (2)	C19—C18—H18B	108.5
C2—C1—Cl1	119.3 (2)	H18A—C18—H18B	107.5
C1—C2—C3	118.8 (2)	C20—C19—C18	118.1 (4)
C1—C2—H2	120.6	C20—C19—H19A	107.8
C3—C2—H2	120.6	C18—C19—H19A	107.8
C4—C3—C2	120.0 (2)	C20—C19—H19B	107.8
C4—C3—H3	120.0	C18—C19—H19B	107.8
C2—C3—H3	120.0	H19A—C19—H19B	107.1
C5—C4—C3	120.3 (2)	C19—C20—H20A	109.5
C5—C4—N1	119.3 (2)	C19—C20—H20B	109.5
C3—C4—N1	120.31 (19)	H20A—C20—H20B	109.5
C4—C5—C6	120.2 (2)	C19—C20—H20C	109.5
C4—C5—H5	119.9	H20A—C20—H20C	109.5
C6—C5—H5	119.9	H20B—C20—H20C	109.5
C1—C6—C5	119.0 (2)	N3—C21—C31	110.33 (19)
C1—C6—H6	120.5	N3—C21—H21	124.8
C5—C6—H6	120.5	C31—C21—H21	124.8
N2—C7—N4	119.96 (19)	C27—C22—C23	120.7 (2)
N2—C7—N1	123.54 (19)	C27—C22—N3	119.9 (2)
N4—C7—N1	116.42 (18)	C23—C22—N3	119.4 (2)
N2—C8—C9	123.51 (18)	C24—C23—C22	120.4 (3)
N2—C8—C31	129.65 (19)	C24—C23—H23	119.8
C9—C8—C31	106.85 (18)	C22—C23—H23	119.8
C8—C9—N3	108.75 (18)	C23—C24—C25	119.1 (3)
C8—C9—C10	122.38 (19)	C23—C24—H24	120.5
N3—C9—C10	128.34 (19)	C25—C24—H24	120.5
O1—C10—C9	128.7 (2)	C24—C25—C26	120.6 (3)
O1—C10—N1	120.30 (19)	C24—C25—H25	119.7
C9—C10—N1	110.90 (18)	C26—C25—H25	119.7
N4—C11—C12	113.0 (2)	C25—C26—C27	120.5 (3)
N4—C11—H11A	109.0	C25—C26—H26	119.7
C12—C11—H11A	109.0	C27—C26—H26	119.7
N4—C11—H11B	109.0	C22—C27—C26	118.7 (3)
C12—C11—H11B	109.0	C22—C27—H27	120.7
H11A—C11—H11B	107.8	C26—C27—H27	120.7
C13—C12—C11	113.8 (2)	O3—C28—O2'	122.2 (4)
C13—C12—H12A	108.8	O3—C28—O2	122.0 (3)
C11—C12—H12A	108.8	O2'—C28—O2	23.0 (4)
C13—C12—H12B	108.8	O3—C28—C31	124.2 (2)
C11—C12—H12B	108.8	O2'—C28—C31	111.8 (4)
H12A—C12—H12B	107.7	O2—C28—C31	113.0 (3)
C12—C13—C14	114.7 (3)	C28—O2—C29	118.9 (7)
C12—C13—H13A	108.6	O2—C29—C30	110.0 (8)
C14—C13—H13A	108.6	O2—C29—H29A	109.7
C12—C13—H13B	108.6	C30—C29—H29A	109.7
C14—C13—H13B	108.6	O2—C29—H29B	109.7
H13A—C13—H13B	107.6	C30—C29—H29B	109.7
C15—C14—C13	115.1 (3)	H29A—C29—H29B	108.2
C15—C14—H14A	108.5	C28—O2'—C29'	115.2 (7)
C13—C14—H14A	108.5	O2'—C29'—C30'	114.0 (8)
C15—C14—H14B	108.5	O2'—C29'—H29C	108.8
C13—C14—H14B	108.5	C30'—C29'—H29C	108.8
H14A—C14—H14B	107.5	O2'—C29'—H29D	108.8
C14—C15—H15A	109.5	C30'—C29'—H29D	108.8
C14—C15—H15B	109.5	H29C—C29'—H29D	107.6
H15A—C15—H15B	109.5	C29'—C30'—H30D	109.5
C14—C15—H15C	109.5	C29'—C30'—H30E	109.5
H15A—C15—H15C	109.5	H30D—C30'—H30E	109.5
H15B—C15—H15C	109.5	C29'—C30'—H30F	109.5
N4—C16—C17	114.1 (2)	H30D—C30'—H30F	109.5
N4—C16—H16A	108.7	H30E—C30'—H30F	109.5
C17—C16—H16A	108.7	C21—C31—C8	106.30 (18)
N4—C16—H16B	108.7	C21—C31—C28	121.2 (2)
C17—C16—H16B	108.7	C8—C31—C28	132.4 (2)
H16A—C16—H16B	107.6	C7—N1—C10	123.25 (17)
C16—C17—C18	114.5 (3)	C7—N1—C4	121.88 (17)
C16—C17—H17A	108.6	C10—N1—C4	113.57 (16)
C18—C17—H17A	108.6	C7—N2—C8	116.07 (18)
C16—C17—H17B	108.6	C21—N3—C9	107.75 (17)
C18—C17—H17B	108.6	C21—N3—C22	124.40 (17)
H17A—C17—H17B	107.6	C9—N3—C22	127.83 (17)
C17—C18—C19	115.1 (3)	C7—N4—C16	115.76 (19)
C17—C18—H18A	108.5	C7—N4—C11	118.94 (19)
C19—C18—H18A	108.5	C16—N4—C11	114.48 (19)
C6—C1—C2—C3	−0.8 (4)	C9—C8—C31—C21	−1.4 (2)
Cl1—C1—C2—C3	179.2 (2)	N2—C8—C31—C28	0.6 (4)
C1—C2—C3—C4	−0.8 (4)	C9—C8—C31—C28	−179.2 (2)
C2—C3—C4—C5	1.9 (4)	O3—C28—C31—C21	4.3 (4)
C2—C3—C4—N1	178.1 (2)	O2'—C28—C31—C21	169.4 (3)
C3—C4—C5—C6	−1.2 (4)	O2—C28—C31—C21	−165.7 (3)
N1—C4—C5—C6	−177.5 (2)	O3—C28—C31—C8	−178.3 (2)
C2—C1—C6—C5	1.5 (4)	O2'—C28—C31—C8	−13.1 (5)
Cl1—C1—C6—C5	−178.5 (2)	O2—C28—C31—C8	11.8 (4)
C4—C5—C6—C1	−0.4 (4)	N2—C7—N1—C10	−3.2 (3)
N2—C8—C9—N3	−178.86 (18)	N4—C7—N1—C10	−179.81 (19)
C31—C8—C9—N3	1.0 (2)	N2—C7—N1—C4	162.9 (2)
N2—C8—C9—C10	−6.6 (3)	N4—C7—N1—C4	−13.7 (3)
C31—C8—C9—C10	173.22 (19)	O1—C10—N1—C7	179.2 (2)
C8—C9—C10—O1	−174.2 (2)	C9—C10—N1—C7	2.8 (3)
N3—C9—C10—O1	−3.5 (4)	O1—C10—N1—C4	12.0 (3)
C8—C9—C10—N1	1.8 (3)	C9—C10—N1—C4	−164.37 (17)
N3—C9—C10—N1	172.48 (19)	C5—C4—N1—C7	−67.3 (3)
N4—C11—C12—C13	−166.9 (2)	C3—C4—N1—C7	116.4 (2)
C11—C12—C13—C14	166.9 (3)	C5—C4—N1—C10	100.1 (2)
C12—C13—C14—C15	−166.3 (3)	C3—C4—N1—C10	−76.2 (3)
N4—C16—C17—C18	176.9 (2)	N4—C7—N2—C8	175.16 (18)
C16—C17—C18—C19	−178.8 (4)	N1—C7—N2—C8	−1.4 (3)
C17—C18—C19—C20	179.9 (5)	C9—C8—N2—C7	6.2 (3)
C27—C22—C23—C24	−1.4 (4)	C31—C8—N2—C7	−173.6 (2)
N3—C22—C23—C24	−179.0 (2)	C31—C21—N3—C9	−0.9 (2)
C22—C23—C24—C25	1.3 (4)	C31—C21—N3—C22	178.10 (19)
C23—C24—C25—C26	−0.3 (5)	C8—C9—N3—C21	−0.1 (2)
C24—C25—C26—C27	−0.7 (5)	C10—C9—N3—C21	−171.8 (2)
C23—C22—C27—C26	0.4 (4)	C8—C9—N3—C22	−179.00 (19)
N3—C22—C27—C26	178.0 (2)	C10—C9—N3—C22	9.3 (3)
C25—C26—C27—C22	0.7 (4)	C27—C22—N3—C21	−121.0 (2)
O3—C28—O2—C29	6.3 (8)	C23—C22—N3—C21	56.6 (3)
O2'—C28—O2—C29	−91.7 (15)	C27—C22—N3—C9	57.7 (3)
C31—C28—O2—C29	176.5 (6)	C23—C22—N3—C9	−124.6 (2)
C28—O2—C29—C30	76.2 (10)	N2—C7—N4—C16	−16.0 (3)
O3—C28—O2'—C29'	−16.2 (8)	N1—C7—N4—C16	160.8 (2)
O2—C28—O2'—C29'	80.6 (15)	N2—C7—N4—C11	126.5 (2)
C31—C28—O2'—C29'	178.3 (5)	N1—C7—N4—C11	−56.8 (3)
C28—O2'—C29'—C30'	−82.2 (10)	C17—C16—N4—C7	−69.9 (3)
N3—C21—C31—C8	1.4 (2)	C17—C16—N4—C11	146.0 (2)
N3—C21—C31—C28	179.49 (19)	C12—C11—N4—C7	135.7 (2)
N2—C8—C31—C21	178.4 (2)	C12—C11—N4—C16	−81.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.57	3.469 (3)	162
C21—H21···O3ii	0.93	2.52	3.375 (3)	153
C24—H24···O1iii	0.93	2.58	3.262 (4)	131
C12—H12A···Cg3	0.97	2.77	3.478 (4)	131
C15—H15A···Cg2iv	0.96	2.86	3.683 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroid of the N1,N2,C7–C10 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.57	3.469 (3)	162
C21—H21⋯O3ii	0.93	2.52	3.375 (3)	153
C24—H24⋯O1iii	0.93	2.58	3.262 (4)	131
C12—H12A⋯Cg3	0.97	2.77	3.478 (4)	131
C15—H15A⋯Cg2iv	0.96	2.86	3.683 (4)	144

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