2-Chloro-8,8-dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione.

The asymmetric unit of the title compound, C(18)H(14)ClNO(3), contains two independent mol-ecules (A and B). In both mol-ecules, the cyclo-hexa-none ring has a chair conformation. The dihedral angles between the pyran ring and the pyridine and chloro-phenyl rings are 2.13 (9) and 2.19 (9)°, respectively, in A, and 0.82 (9) and 1.93 (9)°, respectively, in B. The carbonyl O atoms deviate from the pyran and benzene rings to which they are attached by -0.092 (2) and 0.064 (2) Å, respectively, in A, and by -0.080 (2) and -0.063 (2) Å, respectively, in B. In the crystal, the A mol-ecules are linked via C-H⋯O hydrogen bonds, forming double-stranded chains along [100]. They lie parallel to the double-stranded chains formed by the B mol-ecules, which are also linked via C-H⋯O hydrogen bonds. The chains stack up the c axis in an -A-A-B-B-A-A- manner, with a number of π-π inter-actions involving A and B mol-ecules; the centroid-centroid distances vary from 3.4862 (11) to 3.6848 (11) Å

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶); Sato et al. (2008 ▶). For a related structure, see: Öztürk Yildirim et al. (2012 ▶).

Experimental

Crystal data

C18H14ClNO3

M = 327.75

Triclinic,

a = 11.4135 (4) Å

b = 11.6663 (5) Å

c = 13.5810 (6) Å

α = 69.265 (3)°

β = 73.868 (2)°

γ = 64.998 (5)°

V = 1515.11 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.27 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 = 0.924, T max = 0.949

26747 measured reflections

7488 independent reflections

5384 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.167

S = 0.99

7488 reflections

419 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.33 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001062/su2550sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001062/su2550Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001062/su2550Isup3.cml

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

C18H14ClNO3	Z = 4
Mr = 327.75	F(000) = 680
Triclinic, P1	Dx = 1.437 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4135 (4) Å	Cell parameters from 7488 reflections
b = 11.6663 (5) Å	θ = 1.6–28.4°
c = 13.5810 (6) Å	µ = 0.27 mm−1
α = 69.265 (3)°	T = 293 K
β = 73.868 (2)°	Block, colourless
γ = 64.998 (5)°	0.30 × 0.25 × 0.20 mm
V = 1515.11 (12) Å3

Bruker SMART APEXII area-detector diffractometer	7488 independent reflections
Radiation source: fine-focus sealed tube	5384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
Tmin = 0.924, Tmax = 0.949	k = −15→15
26747 measured reflections	l = −18→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0783P)2 + 0.7873P] where P = (Fo2 + 2Fc2)/3
7488 reflections	(Δ/σ)max < 0.001
419 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.33 e Å−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	0.5452 (2)	0.2391 (2)	0.17141 (17)	0.0507 (5)
C1'	0.7356 (2)	0.4947 (2)	0.32726 (17)	0.0547 (5)
C2	0.6544 (2)	0.2742 (2)	0.14200 (17)	0.0528 (5)
H2	0.7376	0.2098	0.1389	0.063*
C2'	0.7043 (2)	0.3837 (2)	0.35361 (17)	0.0558 (6)
H2'	0.7703	0.3019	0.3552	0.067*
C3'	0.5750 (2)	0.3948 (2)	0.37743 (17)	0.0525 (5)
H3'	0.5532	0.3209	0.3951	0.063*
C3	0.64025 (19)	0.4033 (2)	0.11754 (17)	0.0492 (5)
H3	0.7135	0.4271	0.0973	0.059*
C4	0.51544 (18)	0.4985 (2)	0.12322 (14)	0.0411 (4)
C4'	0.4777 (2)	0.51767 (19)	0.37477 (15)	0.0432 (4)
C5	0.40526 (18)	0.4646 (2)	0.15103 (15)	0.0422 (4)
C5'	0.5084 (2)	0.62854 (19)	0.35132 (15)	0.0435 (4)
C6'	0.6394 (2)	0.6162 (2)	0.32709 (17)	0.0511 (5)
H6'	0.6617	0.6895	0.3109	0.061*
C6	0.4216 (2)	0.3327 (2)	0.17485 (17)	0.0489 (5)
H6	0.3490	0.3083	0.1930	0.059*
C7'	0.4033 (2)	0.75624 (19)	0.35395 (16)	0.0448 (4)
C7	0.27378 (19)	0.5668 (2)	0.15261 (17)	0.0458 (5)
C8	0.27349 (17)	0.6992 (2)	0.13091 (15)	0.0401 (4)
C8'	0.27101 (19)	0.75360 (18)	0.37550 (14)	0.0386 (4)
C9	0.38973 (17)	0.7232 (2)	0.10728 (14)	0.0395 (4)
C9'	0.25063 (19)	0.63696 (18)	0.39621 (15)	0.0403 (4)
C10	0.15855 (18)	0.8078 (2)	0.13264 (16)	0.0431 (4)
H10	0.0782	0.7981	0.1466	0.052*
C10'	0.15975 (19)	0.86517 (18)	0.37749 (15)	0.0406 (4)
H10'	0.1675	0.9457	0.3645	0.049*
C11	0.16353 (18)	0.9292 (2)	0.11373 (16)	0.0433 (4)
C11'	0.0377 (2)	0.85759 (19)	0.39857 (16)	0.0419 (4)
C12	0.28618 (19)	0.9417 (2)	0.09298 (16)	0.0452 (4)
C12'	0.0290 (2)	0.73483 (19)	0.41838 (16)	0.0443 (4)
C13	0.2948 (2)	1.0714 (2)	0.0769 (2)	0.0595 (6)
H13A	0.3744	1.0758	0.0288	0.071*
H13B	0.3009	1.0774	0.1446	0.071*
C13'	−0.1015 (2)	0.7213 (2)	0.4426 (2)	0.0604 (6)
H13C	−0.0945	0.6345	0.4897	0.072*
H13D	−0.1256	0.7286	0.3770	0.072*
C14	0.1788 (2)	1.1890 (2)	0.0318 (2)	0.0574 (6)
C14'	−0.2096 (2)	0.8249 (2)	0.4948 (2)	0.0547 (5)
C15'	−0.2116 (2)	0.9614 (2)	0.4250 (2)	0.0583 (6)
H15A	−0.2399	0.9786	0.3584	0.070*
H15B	−0.2753	1.0267	0.4606	0.070*
C15	0.0525 (2)	1.1739 (2)	0.1015 (2)	0.0668 (7)
H15C	0.0477	1.1832	0.1709	0.080*
H15D	−0.0214	1.2446	0.0697	0.080*
C16	0.0408 (2)	1.0454 (2)	0.1164 (2)	0.0532 (5)
C16'	−0.0816 (2)	0.97710 (19)	0.40067 (17)	0.0470 (5)
C17	0.1858 (3)	1.3168 (3)	0.0318 (3)	0.0908 (11)
H17A	0.2678	1.3235	−0.0077	0.136*
H17B	0.1789	1.3172	0.1038	0.136*
H17C	0.1153	1.3900	−0.0007	0.136*
C17'	−0.3419 (3)	0.8143 (3)	0.5042 (3)	0.0808 (9)
H17D	−0.4098	0.8793	0.5368	0.121*
H17E	−0.3400	0.7283	0.5472	0.121*
H17F	−0.3586	0.8286	0.4345	0.121*
C18	0.1796 (3)	1.1930 (3)	−0.0825 (2)	0.0802 (8)
H18A	0.2588	1.2024	−0.1261	0.120*
H18B	0.1058	1.2663	−0.1102	0.120*
H18C	0.1746	1.1130	−0.0826	0.120*
C18'	−0.1844 (2)	0.8035 (3)	0.6060 (2)	0.0637 (6)
H18D	−0.2542	0.8674	0.6386	0.096*
H18E	−0.1031	0.8129	0.6004	0.096*
H18F	−0.1803	0.7168	0.6487	0.096*
N1	0.39826 (15)	0.83855 (18)	0.08958 (14)	0.0470 (4)
N1'	0.13495 (18)	0.62525 (16)	0.41741 (14)	0.0474 (4)
O1	0.17423 (15)	0.54410 (18)	0.16973 (18)	0.0723 (5)
O1'	0.42395 (16)	0.85595 (16)	0.33981 (16)	0.0663 (5)
O2'	0.35174 (14)	0.52027 (13)	0.39693 (12)	0.0485 (3)
O2	0.50909 (12)	0.62565 (14)	0.10098 (11)	0.0463 (3)
O3	−0.06431 (15)	1.03402 (18)	0.13335 (19)	0.0777 (6)
O3'	−0.07287 (16)	1.08344 (15)	0.38172 (16)	0.0648 (5)
Cl1'	0.89836 (6)	0.48087 (7)	0.29361 (6)	0.0808 (2)
Cl1	0.56258 (7)	0.07546 (6)	0.20440 (6)	0.0733 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0506 (12)	0.0466 (11)	0.0461 (11)	−0.0068 (9)	−0.0091 (9)	−0.0145 (9)
C1'	0.0457 (11)	0.0560 (13)	0.0444 (11)	−0.0033 (10)	−0.0101 (9)	−0.0091 (9)
C2	0.0416 (11)	0.0522 (12)	0.0490 (12)	0.0025 (9)	−0.0083 (9)	−0.0185 (10)
C2'	0.0551 (13)	0.0442 (11)	0.0447 (11)	0.0062 (10)	−0.0117 (9)	−0.0120 (9)
C3'	0.0608 (13)	0.0367 (10)	0.0450 (11)	−0.0027 (9)	−0.0093 (9)	−0.0112 (8)
C3	0.0332 (9)	0.0575 (13)	0.0469 (11)	−0.0066 (9)	−0.0038 (8)	−0.0166 (9)
C4	0.0350 (9)	0.0468 (11)	0.0336 (9)	−0.0076 (8)	−0.0048 (7)	−0.0110 (8)
C4'	0.0483 (11)	0.0365 (10)	0.0341 (9)	−0.0051 (8)	−0.0065 (8)	−0.0097 (7)
C5	0.0338 (9)	0.0493 (11)	0.0369 (9)	−0.0075 (8)	−0.0043 (7)	−0.0141 (8)
C5'	0.0464 (11)	0.0370 (10)	0.0361 (9)	−0.0053 (8)	−0.0077 (8)	−0.0083 (7)
C6'	0.0470 (11)	0.0468 (11)	0.0470 (11)	−0.0082 (9)	−0.0095 (9)	−0.0073 (9)
C6	0.0449 (11)	0.0517 (12)	0.0473 (11)	−0.0138 (9)	−0.0056 (9)	−0.0157 (9)
C7'	0.0469 (11)	0.0342 (10)	0.0457 (11)	−0.0085 (8)	−0.0088 (8)	−0.0082 (8)
C7	0.0339 (9)	0.0511 (11)	0.0497 (11)	−0.0112 (8)	−0.0024 (8)	−0.0184 (9)
C8	0.0304 (8)	0.0490 (11)	0.0378 (9)	−0.0102 (8)	−0.0050 (7)	−0.0136 (8)
C8'	0.0450 (10)	0.0310 (9)	0.0356 (9)	−0.0095 (8)	−0.0058 (7)	−0.0097 (7)
C9	0.0274 (8)	0.0468 (10)	0.0374 (9)	−0.0075 (7)	−0.0050 (7)	−0.0107 (8)
C9'	0.0474 (10)	0.0304 (9)	0.0375 (9)	−0.0086 (8)	−0.0046 (8)	−0.0111 (7)
C10	0.0287 (8)	0.0523 (11)	0.0471 (11)	−0.0125 (8)	−0.0043 (7)	−0.0156 (9)
C10'	0.0469 (10)	0.0277 (8)	0.0429 (10)	−0.0105 (8)	−0.0068 (8)	−0.0082 (7)
C11	0.0306 (9)	0.0465 (11)	0.0479 (11)	−0.0087 (8)	−0.0063 (7)	−0.0131 (9)
C11'	0.0445 (10)	0.0338 (9)	0.0436 (10)	−0.0110 (8)	−0.0059 (8)	−0.0106 (8)
C12	0.0341 (9)	0.0500 (11)	0.0473 (11)	−0.0127 (8)	−0.0071 (8)	−0.0108 (9)
C12'	0.0477 (11)	0.0365 (10)	0.0477 (11)	−0.0134 (8)	−0.0038 (8)	−0.0150 (8)
C13	0.0414 (11)	0.0538 (13)	0.0837 (17)	−0.0162 (10)	−0.0119 (11)	−0.0185 (12)
C13'	0.0535 (13)	0.0485 (12)	0.0853 (17)	−0.0205 (10)	−0.0039 (12)	−0.0276 (12)
C14	0.0433 (11)	0.0438 (11)	0.0814 (16)	−0.0128 (9)	−0.0082 (11)	−0.0174 (11)
C14'	0.0394 (10)	0.0427 (11)	0.0792 (16)	−0.0130 (9)	−0.0093 (10)	−0.0153 (11)
C15'	0.0441 (11)	0.0435 (11)	0.0791 (16)	−0.0095 (9)	−0.0169 (11)	−0.0091 (11)
C15	0.0426 (12)	0.0531 (14)	0.100 (2)	−0.0092 (10)	0.0002 (12)	−0.0335 (13)
C16	0.0349 (10)	0.0497 (12)	0.0690 (14)	−0.0089 (9)	−0.0048 (9)	−0.0194 (10)
C16'	0.0458 (11)	0.0342 (10)	0.0533 (12)	−0.0083 (8)	−0.0090 (9)	−0.0096 (8)
C17	0.0578 (16)	0.0537 (15)	0.164 (3)	−0.0169 (13)	−0.0138 (18)	−0.0396 (18)
C17'	0.0481 (14)	0.0622 (16)	0.133 (3)	−0.0216 (12)	−0.0126 (15)	−0.0261 (17)
C18	0.085 (2)	0.0621 (16)	0.0777 (19)	−0.0252 (15)	−0.0165 (15)	0.0008 (14)
C18'	0.0492 (12)	0.0575 (14)	0.0698 (16)	−0.0152 (11)	0.0025 (11)	−0.0143 (12)
N1	0.0304 (8)	0.0511 (10)	0.0536 (10)	−0.0118 (7)	−0.0061 (7)	−0.0111 (8)
N1'	0.0508 (10)	0.0352 (8)	0.0536 (10)	−0.0139 (7)	−0.0004 (8)	−0.0170 (7)
O1	0.0344 (8)	0.0593 (10)	0.1242 (16)	−0.0154 (7)	−0.0048 (9)	−0.0333 (10)
O1'	0.0514 (9)	0.0411 (8)	0.1038 (14)	−0.0149 (7)	−0.0113 (9)	−0.0193 (8)
O2'	0.0505 (8)	0.0299 (7)	0.0568 (9)	−0.0071 (6)	−0.0044 (6)	−0.0141 (6)
O2	0.0271 (6)	0.0479 (8)	0.0540 (8)	−0.0069 (6)	−0.0029 (5)	−0.0133 (6)
O3	0.0295 (8)	0.0578 (10)	0.1401 (18)	−0.0059 (7)	−0.0090 (9)	−0.0355 (11)
O3'	0.0524 (9)	0.0339 (8)	0.0981 (13)	−0.0090 (7)	−0.0087 (9)	−0.0167 (8)
Cl1'	0.0443 (3)	0.0753 (5)	0.0916 (5)	0.0002 (3)	−0.0115 (3)	−0.0129 (4)
Cl1	0.0716 (4)	0.0471 (3)	0.0927 (5)	−0.0067 (3)	−0.0227 (3)	−0.0194 (3)

C1—C6	1.372 (3)	C11—C12	1.409 (3)
C1—C2	1.385 (3)	C11—C16	1.484 (3)
C1—Cl1	1.735 (2)	C11'—C12'	1.402 (3)
C1'—C6'	1.377 (3)	C11'—C16'	1.483 (3)
C1'—C2'	1.388 (4)	C12—N1	1.339 (3)
C1'—Cl1'	1.736 (2)	C12—C13	1.492 (3)
C2—C3	1.370 (3)	C12'—N1'	1.339 (3)
C2—H2	0.9300	C12'—C13'	1.497 (3)
C2'—C3'	1.379 (3)	C13—C14	1.527 (3)
C2'—H2'	0.9300	C13—H13A	0.9700
C3'—C4'	1.389 (3)	C13—H13B	0.9700
C3'—H3'	0.9300	C13'—C14'	1.532 (3)
C3—C4	1.390 (3)	C13'—H13C	0.9700
C3—H3	0.9300	C13'—H13D	0.9700
C4—O2	1.378 (2)	C14—C17	1.527 (3)
C4—C5	1.390 (3)	C14—C18	1.533 (4)
C4'—O2'	1.374 (3)	C14—C15	1.531 (3)
C4'—C5'	1.388 (3)	C14'—C18'	1.529 (4)
C5—C6	1.395 (3)	C14'—C17'	1.533 (3)
C5—C7	1.470 (3)	C14'—C15'	1.533 (3)
C5'—C6'	1.393 (3)	C15'—C16'	1.503 (3)
C5'—C7'	1.471 (3)	C15'—H15A	0.9700
C6'—H6'	0.9300	C15'—H15B	0.9700
C6—H6	0.9300	C15—C16	1.499 (3)
C7'—O1'	1.222 (2)	C15—H15C	0.9700
C7'—C8'	1.468 (3)	C15—H15D	0.9700
C7—O1	1.216 (2)	C16—O3	1.212 (3)
C7—C8	1.466 (3)	C16'—O3'	1.216 (2)
C8—C10	1.387 (3)	C17—H17A	0.9600
C8—C9	1.398 (3)	C17—H17B	0.9600
C8'—C10'	1.384 (3)	C17—H17C	0.9600
C8'—C9'	1.395 (3)	C17'—H17D	0.9600
C9—N1	1.322 (3)	C17'—H17E	0.9600
C9—O2	1.361 (2)	C17'—H17F	0.9600
C9'—N1'	1.326 (3)	C18—H18A	0.9600
C9'—O2'	1.362 (2)	C18—H18B	0.9600
C10—C11	1.371 (3)	C18—H18C	0.9600
C10—H10	0.9300	C18'—H18D	0.9600
C10'—C11'	1.377 (3)	C18'—H18E	0.9600
C10'—H10'	0.9300	C18'—H18F	0.9600
C6—C1—C2	120.8 (2)	C11'—C12'—C13'	120.59 (18)
C6—C1—Cl1	118.75 (18)	C12—C13—C14	113.78 (19)
C2—C1—Cl1	120.41 (17)	C12—C13—H13A	108.8
C6'—C1'—C2'	121.0 (2)	C14—C13—H13A	108.8
C6'—C1'—Cl1'	119.3 (2)	C12—C13—H13B	108.8
C2'—C1'—Cl1'	119.64 (17)	C14—C13—H13B	108.8
C3—C2—C1	120.21 (19)	H13A—C13—H13B	107.7
C3—C2—H2	119.9	C12'—C13'—C14'	113.01 (18)
C1—C2—H2	119.9	C12'—C13'—H13C	109.0
C3'—C2'—C1'	119.8 (2)	C14'—C13'—H13C	109.0
C3'—C2'—H2'	120.1	C12'—C13'—H13D	109.0
C1'—C2'—H2'	120.1	C14'—C13'—H13D	109.0
C2'—C3'—C4'	119.2 (2)	H13C—C13'—H13D	107.8
C2'—C3'—H3'	120.4	C13—C14—C17	110.4 (2)
C4'—C3'—H3'	120.4	C13—C14—C18	109.7 (2)
C2—C3—C4	119.4 (2)	C17—C14—C18	109.3 (2)
C2—C3—H3	120.3	C13—C14—C15	108.6 (2)
C4—C3—H3	120.3	C17—C14—C15	109.3 (2)
O2—C4—C3	116.00 (18)	C18—C14—C15	109.5 (2)
O2—C4—C5	123.13 (17)	C18'—C14'—C17'	109.1 (2)
C3—C4—C5	120.9 (2)	C18'—C14'—C13'	110.3 (2)
O2'—C4'—C5'	123.44 (17)	C17'—C14'—C13'	109.4 (2)
O2'—C4'—C3'	115.37 (19)	C18'—C14'—C15'	109.7 (2)
C5'—C4'—C3'	121.2 (2)	C17'—C14'—C15'	109.6 (2)
C4—C5—C6	118.95 (18)	C13'—C14'—C15'	108.7 (2)
C4—C5—C7	120.38 (19)	C16'—C15'—C14'	113.85 (18)
C6—C5—C7	120.65 (18)	C16'—C15'—H15A	108.8
C4'—C5'—C6'	119.05 (18)	C14'—C15'—H15A	108.8
C4'—C5'—C7'	119.92 (19)	C16'—C15'—H15B	108.8
C6'—C5'—C7'	121.02 (19)	C14'—C15'—H15B	108.8
C1'—C6'—C5'	119.6 (2)	H15A—C15'—H15B	107.7
C1'—C6'—H6'	120.2	C16—C15—C14	114.19 (19)
C5'—C6'—H6'	120.2	C16—C15—H15C	108.7
C1—C6—C5	119.7 (2)	C14—C15—H15C	108.7
C1—C6—H6	120.1	C16—C15—H15D	108.7
C5—C6—H6	120.1	C14—C15—H15D	108.7
O1'—C7'—C8'	122.76 (18)	H15C—C15—H15D	107.6
O1'—C7'—C5'	123.1 (2)	O3—C16—C11	120.3 (2)
C8'—C7'—C5'	114.11 (17)	O3—C16—C15	122.1 (2)
O1—C7—C8	122.87 (19)	C11—C16—C15	117.52 (18)
O1—C7—C5	123.4 (2)	O3'—C16'—C11'	120.49 (19)
C8—C7—C5	113.76 (17)	O3'—C16'—C15'	121.99 (19)
C10—C8—C9	116.18 (18)	C11'—C16'—C15'	117.51 (18)
C10—C8—C7	122.19 (17)	C14—C17—H17A	109.5
C9—C8—C7	121.63 (17)	C14—C17—H17B	109.5
C10'—C8'—C9'	116.13 (18)	H17A—C17—H17B	109.5
C10'—C8'—C7'	122.48 (17)	C14—C17—H17C	109.5
C9'—C8'—C7'	121.38 (17)	H17A—C17—H17C	109.5
N1—C9—O2	112.46 (16)	H17B—C17—H17C	109.5
N1—C9—C8	125.55 (17)	C14'—C17'—H17D	109.5
O2—C9—C8	121.99 (18)	C14'—C17'—H17E	109.5
N1'—C9'—O2'	112.55 (16)	H17D—C17'—H17E	109.5
N1'—C9'—C8'	125.45 (17)	C14'—C17'—H17F	109.5
O2'—C9'—C8'	121.99 (18)	H17D—C17'—H17F	109.5
C11—C10—C8	119.92 (17)	H17E—C17'—H17F	109.5
C11—C10—H10	120.0	C14—C18—H18A	109.5
C8—C10—H10	120.0	C14—C18—H18B	109.5
C11'—C10'—C8'	120.33 (17)	H18A—C18—H18B	109.5
C11'—C10'—H10'	119.8	C14—C18—H18C	109.5
C8'—C10'—H10'	119.8	H18A—C18—H18C	109.5
C10—C11—C12	119.19 (18)	H18B—C18—H18C	109.5
C10—C11—C16	120.10 (17)	C14'—C18'—H18D	109.5
C12—C11—C16	120.71 (19)	C14'—C18'—H18E	109.5
C10'—C11'—C12'	118.57 (18)	H18D—C18'—H18E	109.5
C10'—C11'—C16'	120.37 (17)	C14'—C18'—H18F	109.5
C12'—C11'—C16'	121.06 (18)	H18D—C18'—H18F	109.5
N1—C12—C11	121.82 (19)	H18E—C18'—H18F	109.5
N1—C12—C13	117.67 (18)	C9—N1—C12	117.33 (16)
C11—C12—C13	120.49 (18)	C9'—N1'—C12'	117.15 (17)
N1'—C12'—C11'	122.37 (19)	C9'—O2'—C4'	119.03 (15)
N1'—C12'—C13'	117.04 (18)	C9—O2—C4	118.93 (15)
C6—C1—C2—C3	1.1 (3)	C8—C10—C11—C16	−179.46 (19)
Cl1—C1—C2—C3	−179.03 (17)	C8'—C10'—C11'—C12'	0.3 (3)
C6'—C1'—C2'—C3'	1.7 (3)	C8'—C10'—C11'—C16'	−179.97 (18)
Cl1'—C1'—C2'—C3'	−178.16 (17)	C10—C11—C12—N1	1.0 (3)
C1'—C2'—C3'—C4'	−0.1 (3)	C16—C11—C12—N1	−179.6 (2)
C1—C2—C3—C4	0.4 (3)	C10—C11—C12—C13	−177.3 (2)
C2—C3—C4—O2	177.88 (18)	C16—C11—C12—C13	2.0 (3)
C2—C3—C4—C5	−1.4 (3)	C10'—C11'—C12'—N1'	−0.1 (3)
C2'—C3'—C4'—O2'	178.43 (18)	C16'—C11'—C12'—N1'	−179.75 (19)
C2'—C3'—C4'—C5'	−1.7 (3)	C10'—C11'—C12'—C13'	179.5 (2)
O2—C4—C5—C6	−178.33 (17)	C16'—C11'—C12'—C13'	−0.2 (3)
C3—C4—C5—C6	0.9 (3)	N1—C12—C13—C14	153.4 (2)
O2—C4—C5—C7	3.2 (3)	C11—C12—C13—C14	−28.2 (3)
C3—C4—C5—C7	−177.54 (18)	N1'—C12'—C13'—C14'	151.8 (2)
O2'—C4'—C5'—C6'	−178.27 (18)	C11'—C12'—C13'—C14'	−27.8 (3)
C3'—C4'—C5'—C6'	1.9 (3)	C12—C13—C14—C17	172.4 (2)
O2'—C4'—C5'—C7'	2.7 (3)	C12—C13—C14—C18	−67.0 (3)
C3'—C4'—C5'—C7'	−177.18 (19)	C12—C13—C14—C15	52.6 (3)
C2'—C1'—C6'—C5'	−1.5 (3)	C12'—C13'—C14'—C18'	−66.8 (3)
Cl1'—C1'—C6'—C5'	178.33 (16)	C12'—C13'—C14'—C17'	173.1 (2)
C4'—C5'—C6'—C1'	−0.3 (3)	C12'—C13'—C14'—C15'	53.5 (3)
C7'—C5'—C6'—C1'	178.77 (19)	C18'—C14'—C15'—C16'	66.6 (3)
C2—C1—C6—C5	−1.6 (3)	C17'—C14'—C15'—C16'	−173.6 (2)
Cl1—C1—C6—C5	178.52 (16)	C13'—C14'—C15'—C16'	−54.1 (3)
C4—C5—C6—C1	0.6 (3)	C13—C14—C15—C16	−53.8 (3)
C7—C5—C6—C1	179.05 (19)	C17—C14—C15—C16	−174.3 (3)
C4'—C5'—C7'—O1'	175.9 (2)	C18—C14—C15—C16	65.9 (3)
C6'—C5'—C7'—O1'	−3.1 (3)	C10—C11—C16—O3	−1.4 (4)
C4'—C5'—C7'—C8'	−3.9 (3)	C12—C11—C16—O3	179.3 (2)
C6'—C5'—C7'—C8'	177.10 (18)	C10—C11—C16—C15	176.5 (2)
C4—C5—C7—O1	175.2 (2)	C12—C11—C16—C15	−2.8 (3)
C6—C5—C7—O1	−3.2 (3)	C14—C15—C16—O3	−152.3 (3)
C4—C5—C7—C8	−4.4 (3)	C14—C15—C16—C11	29.9 (3)
C6—C5—C7—C8	177.16 (18)	C10'—C11'—C16'—O3'	1.5 (3)
O1—C7—C8—C10	2.6 (3)	C12'—C11'—C16'—O3'	−178.8 (2)
C5—C7—C8—C10	−177.72 (18)	C10'—C11'—C16'—C15'	−179.6 (2)
O1—C7—C8—C9	−177.4 (2)	C12'—C11'—C16'—C15'	0.1 (3)
C5—C7—C8—C9	2.2 (3)	C14'—C15'—C16'—O3'	−152.9 (2)
O1'—C7'—C8'—C10'	2.4 (3)	C14'—C15'—C16'—C11'	28.2 (3)
C5'—C7'—C8'—C10'	−177.78 (17)	O2—C9—N1—C12	179.43 (17)
O1'—C7'—C8'—C9'	−177.0 (2)	C8—C9—N1—C12	−1.1 (3)
C5'—C7'—C8'—C9'	2.8 (3)	C11—C12—N1—C9	−0.5 (3)
C10—C8—C9—N1	1.9 (3)	C13—C12—N1—C9	177.90 (19)
C7—C8—C9—N1	−178.08 (19)	O2'—C9'—N1'—C12'	−179.88 (17)
C10—C8—C9—O2	−178.65 (17)	C8'—C9'—N1'—C12'	0.4 (3)
C7—C8—C9—O2	1.4 (3)	C11'—C12'—N1'—C9'	−0.3 (3)
C10'—C8'—C9'—N1'	−0.1 (3)	C13'—C12'—N1'—C9'	−179.85 (19)
C7'—C8'—C9'—N1'	179.33 (18)	N1'—C9'—O2'—C4'	179.10 (16)
C10'—C8'—C9'—O2'	−179.83 (17)	C8'—C9'—O2'—C4'	−1.2 (3)
C7'—C8'—C9'—O2'	−0.4 (3)	C5'—C4'—O2'—C9'	0.0 (3)
C9—C8—C10—C11	−1.2 (3)	C3'—C4'—O2'—C9'	179.84 (17)
C7—C8—C10—C11	178.79 (19)	N1—C9—O2—C4	176.59 (16)
C9'—C8'—C10'—C11'	−0.3 (3)	C8—C9—O2—C4	−2.9 (3)
C7'—C8'—C10'—C11'	−179.69 (18)	C3—C4—O2—C9	−178.66 (17)
C8—C10—C11—C12	−0.2 (3)	C5—C4—O2—C9	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.33	3.255 (3)	174
C2′—H2′···O3′i	0.93	2.38	3.309 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.33	3.255 (3)	174
C2′—H2′⋯O3′i	0.93	2.38	3.309 (3)	173

Symmetry code: (i) .