10-(1,3-Benzo­thia­zol-2-yl)-2,3,6,7-tetra­hydro-1H,5H-11H-[1]­benzo­pyrano­[6,7,8-ij]-quinoliz-11-one

The title compound, C₂₂H₁₈N₂O₂S, is also known as coumarin 545. The 2-benzo­thia­zolyl and quinolizine groups are each nearly planar and are twisted slightly at 6.4 (1)° to each other. The mol­ecules are stacked in layers oblique to (110) and (111).

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.143
• Data-to-parameter ratio = 15.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1998); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.

10-(1,3-Benzothiazol-2-yl)-2,3,6,7-tetrahydro-1H,5H-11H- [1]benzopyrano[6,7,8-ij]-quinoliz-11-one1

Crystal data

C22H18N2O2S	F(000) = 784
Mr = 374.44	Dx = 1.400 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 12.2528 (18) Å	Cell parameters from 20 reflections
b = 11.702 (2) Å	θ = 18.8–22.4°
c = 13.263 (2) Å	µ = 0.20 mm^−1
β = 110.915 (10)°	T = 296 K
V = 1776.3 (5) Å^3	Prism, red
Z = 4	0.60 × 0.50 × 0.50 mm

Data collection

Rigaku AFC-6S diffractometer	2088 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
\2θ/ω scans	h = 0→15
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.888, Tmax = 0.903	l = −17→16
4241 measured reflections	3 standard reflections every 150 reflections
4057 independent reflections	intensity decay: 0.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 1.155P] where P = (Fo^2 + 2Fc^2)/3
4057 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.30 e Å^−3
7 restraints	Δρmin = −0.25 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1'	0.34100 (6)	0.52347 (7)	0.50059 (6)	0.0475 (2)
O1	0.13666 (15)	0.24720 (17)	0.59469 (14)	0.0449 (5)
O11	0.30114 (18)	0.3358 (2)	0.61493 (19)	0.0769 (8)
N3'	0.13419 (19)	0.56300 (19)	0.35875 (18)	0.0405 (5)
N15	−0.19795 (18)	0.0170 (2)	0.54777 (18)	0.0431 (6)
C2'	0.1903 (2)	0.4962 (2)	0.4393 (2)	0.0368 (6)
C2	0.1971 (2)	0.3316 (3)	0.5639 (2)	0.0472 (7)
C3	0.1318 (2)	0.4047 (2)	0.4748 (2)	0.0377 (6)
C4	0.0152 (2)	0.3829 (2)	0.4216 (2)	0.0384 (6)
H4A	−0.0264	0.4291	0.3636	0.046*
C4'	0.1766 (3)	0.7253 (3)	0.2590 (3)	0.0508 (8)
H4'A	0.0992	0.7323	0.2130	0.061*
C5'	0.2608 (3)	0.7972 (3)	0.2491 (3)	0.0613 (9)
H5'A	0.2398	0.8536	0.1963	0.074*
C5	−0.1611 (2)	0.2648 (2)	0.3964 (2)	0.0416 (7)
H5A	−0.2047	0.3080	0.3368	0.050*
C6	−0.2140 (2)	0.1758 (2)	0.4271 (2)	0.0401 (6)
C6'	0.3766 (3)	0.7872 (3)	0.3166 (3)	0.0620 (9)
H6'A	0.4319	0.8365	0.3075	0.074*
C7	−0.1477 (2)	0.1077 (2)	0.5184 (2)	0.0346 (6)
C7'	0.4116 (3)	0.7055 (3)	0.3967 (3)	0.0547 (8)
H7'A	0.4895	0.6990	0.4414	0.066*
C8	−0.0287 (2)	0.1348 (2)	0.57605 (19)	0.0357 (6)
C8'	0.3266 (2)	0.6327 (2)	0.4090 (2)	0.0422 (6)
C9	0.0189 (2)	0.2261 (2)	0.5401 (2)	0.0349 (6)
C9'	0.2093 (2)	0.6414 (2)	0.3396 (2)	0.0398 (6)
C10	−0.0438 (2)	0.2938 (2)	0.4511 (2)	0.0356 (6)
C12A	−0.3422 (4)	0.1522 (4)	0.3722 (4)	0.0435 (12)	0.740 (7)
H12A	−0.3683	0.1783	0.2979	0.052*	0.740 (7)
H12B	−0.3864	0.1925	0.4089	0.052*	0.740 (7)
C13A	−0.3617 (4)	0.0235 (4)	0.3757 (4)	0.0549 (14)	0.740 (7)
H13A	−0.4444	0.0068	0.3419	0.066*	0.740 (7)
H13B	−0.3209	−0.0158	0.3352	0.066*	0.740 (7)
C14A	−0.3189 (5)	−0.0189 (7)	0.4883 (7)	0.051 (2)	0.740 (7)
H14A	−0.3691	0.0100	0.5250	0.062*	0.740 (7)
H14B	−0.3232	−0.1016	0.4879	0.062*	0.740 (7)
C16A	−0.1384 (5)	−0.0492 (8)	0.6467 (5)	0.0558 (19)	0.740 (7)
H16A	−0.1919	−0.0585	0.6851	0.067*	0.740 (7)
H16B	−0.1215	−0.1247	0.6259	0.067*	0.740 (7)
C17A	−0.0325 (3)	−0.0013 (4)	0.7191 (3)	0.0449 (12)	0.740 (7)
H17A	0.0125	−0.0622	0.7648	0.054*	0.740 (7)
H17C	−0.0521	0.0528	0.7653	0.054*	0.740 (7)
C18A	0.0446 (7)	0.0585 (9)	0.6693 (9)	0.0415 (19)	0.740 (7)
H18A	0.0861	0.0023	0.6428	0.050*	0.740 (7)
H18B	0.1020	0.1046	0.7235	0.050*	0.740 (7)
C12B	−0.3312 (12)	0.1218 (13)	0.3457 (11)	0.038 (4)*	0.260 (7)
H12C	−0.3797	0.1808	0.2999	0.045*	0.260 (7)
H12D	−0.3136	0.0653	0.3002	0.045*	0.260 (7)
C13B	−0.3948 (11)	0.0659 (13)	0.4132 (11)	0.056 (4)*	0.260 (7)
H13C	−0.4167	0.1236	0.4550	0.067*	0.260 (7)
H13D	−0.4655	0.0288	0.3662	0.067*	0.260 (7)
C14B	−0.317 (2)	−0.019 (3)	0.487 (3)	0.115 (15)*	0.260 (7)
H14C	−0.3526	−0.0440	0.5374	0.137*	0.260 (7)
H14D	−0.3128	−0.0856	0.4439	0.137*	0.260 (7)
C16B	−0.1288 (11)	−0.0634 (19)	0.6262 (14)	0.030 (4)*	0.260 (7)
H16C	−0.1618	−0.0692	0.6824	0.036*	0.260 (7)
H16D	−0.1379	−0.1375	0.5914	0.036*	0.260 (7)
C17B	−0.0081 (9)	−0.0426 (10)	0.6764 (10)	0.039 (3)*	0.260 (7)
H17B	0.0324	−0.0914	0.6421	0.047*	0.260 (7)
H17D	0.0146	−0.0673	0.7509	0.047*	0.260 (7)
C18B	0.037 (3)	0.077 (2)	0.677 (4)	0.060 (12)*	0.260 (7)
H18C	0.0291	0.1192	0.7369	0.072*	0.260 (7)
H18D	0.1188	0.0746	0.6860	0.072*	0.260 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1'	0.0402 (4)	0.0505 (4)	0.0461 (4)	−0.0103 (3)	0.0085 (3)	0.0004 (4)
O1	0.0356 (10)	0.0530 (12)	0.0364 (10)	−0.0117 (9)	0.0011 (8)	0.0106 (9)
O11	0.0446 (12)	0.0920 (19)	0.0688 (16)	−0.0256 (12)	−0.0107 (11)	0.0304 (14)
N3'	0.0387 (12)	0.0393 (13)	0.0455 (13)	−0.0019 (10)	0.0176 (10)	0.0017 (11)
N15	0.0381 (12)	0.0451 (14)	0.0410 (13)	−0.0077 (11)	0.0081 (10)	0.0065 (11)
C2'	0.0388 (13)	0.0360 (15)	0.0361 (14)	−0.0036 (11)	0.0139 (11)	−0.0040 (11)
C2	0.0403 (15)	0.0534 (19)	0.0409 (16)	−0.0129 (13)	0.0060 (13)	0.0040 (14)
C3	0.0385 (13)	0.0400 (15)	0.0347 (14)	−0.0041 (11)	0.0131 (11)	−0.0004 (11)
C4	0.0360 (13)	0.0441 (16)	0.0335 (14)	0.0044 (12)	0.0104 (11)	0.0069 (12)
C4'	0.0557 (17)	0.0419 (17)	0.0611 (19)	0.0071 (14)	0.0285 (15)	0.0118 (15)
C5'	0.073 (2)	0.0453 (19)	0.079 (2)	0.0031 (17)	0.0446 (19)	0.0117 (18)
C5	0.0324 (13)	0.0502 (17)	0.0373 (15)	0.0053 (12)	0.0067 (11)	0.0113 (13)
C6	0.0304 (12)	0.0475 (17)	0.0391 (15)	−0.0008 (12)	0.0083 (11)	0.0067 (13)
C6'	0.076 (2)	0.0433 (19)	0.084 (2)	−0.0193 (17)	0.050 (2)	−0.0075 (18)
C7	0.0343 (13)	0.0383 (15)	0.0318 (14)	0.0003 (11)	0.0126 (11)	0.0007 (11)
C7'	0.0535 (18)	0.0475 (18)	0.069 (2)	−0.0146 (15)	0.0295 (16)	−0.0136 (17)
C8	0.0367 (13)	0.0408 (15)	0.0277 (13)	−0.0009 (11)	0.0090 (11)	0.0012 (11)
C8'	0.0486 (15)	0.0365 (15)	0.0480 (17)	−0.0065 (12)	0.0250 (13)	−0.0090 (13)
C9	0.0304 (12)	0.0416 (15)	0.0287 (12)	−0.0014 (11)	0.0060 (10)	−0.0022 (11)
C9'	0.0445 (15)	0.0339 (14)	0.0490 (16)	−0.0011 (12)	0.0263 (13)	−0.0040 (13)
C10	0.0319 (12)	0.0413 (15)	0.0322 (13)	−0.0006 (11)	0.0095 (11)	0.0017 (12)
C12A	0.031 (2)	0.053 (3)	0.042 (3)	−0.002 (2)	0.0069 (18)	−0.002 (2)
C13A	0.041 (2)	0.061 (3)	0.050 (3)	−0.015 (2)	0.0008 (19)	−0.010 (2)
C14A	0.029 (2)	0.045 (3)	0.065 (4)	−0.0176 (18)	0.0002 (17)	0.017 (2)
C16A	0.063 (3)	0.061 (4)	0.049 (4)	0.003 (3)	0.027 (3)	0.019 (3)
C17A	0.048 (2)	0.046 (3)	0.037 (2)	0.0038 (18)	0.0099 (17)	0.0128 (18)
C18A	0.033 (3)	0.047 (3)	0.036 (3)	−0.001 (3)	0.002 (2)	0.012 (3)

Geometric parameters (Å, º)

S1'—C8'	1.729 (3)	C8—C18A	1.530 (9)
S1'—C2'	1.761 (3)	C8'—C9'	1.406 (4)
O1—C2	1.381 (3)	C9—C10	1.402 (3)
O1—C9	1.386 (3)	C12A—C13A	1.528 (6)
O11—C2	1.212 (3)	C12A—H12A	0.9700
N3'—C2'	1.304 (3)	C12A—H12B	0.9700
N3'—C9'	1.386 (3)	C13A—C14A	1.481 (8)
N15—C7	1.352 (3)	C13A—H13A	0.9700
N15—C16B	1.43 (2)	C13A—H13B	0.9700
N15—C14B	1.45 (3)	C14A—H14A	0.9700
N15—C14A	1.470 (6)	C14A—H14B	0.9700
N15—C16A	1.473 (7)	C16A—C17A	1.425 (6)
C2'—C3	1.457 (4)	C16A—H16A	0.9700
C2—C3	1.448 (4)	C16A—H16B	0.9700
C3—C4	1.373 (3)	C17A—C18A	1.505 (9)
C4—C10	1.401 (4)	C17A—H17A	0.9700
C4—H4A	0.9300	C17A—H17C	0.9700
C4'—C5'	1.373 (4)	C18A—H18A	0.9700
C4'—C9'	1.401 (4)	C18A—H18B	0.9700
C4'—H4'A	0.9300	C12B—C13B	1.528 (14)
C5'—C6'	1.386 (5)	C12B—H12C	0.9700
C5'—H5'A	0.9300	C12B—H12D	0.9700
C5—C6	1.363 (4)	C13B—C14B	1.481 (17)
C5—C10	1.402 (3)	C13B—H13C	0.9700
C5—H5A	0.9300	C13B—H13D	0.9700
C6—C7	1.435 (4)	C14B—H14C	0.9700
C6—C12A	1.502 (5)	C14B—H14D	0.9700
C6—C12B	1.587 (15)	C16B—C17B	1.409 (13)
C6'—C7'	1.379 (5)	C16B—H16C	0.9700
C6'—H6'A	0.9300	C16B—H16D	0.9700
C7—C8	1.420 (3)	C17B—C18B	1.502 (18)
C7'—C8'	1.400 (4)	C17B—H17B	0.9700
C7'—H7'A	0.9300	C17B—H17D	0.9700
C8—C9	1.380 (4)	C18B—H18C	0.9700
C8—C18B	1.46 (4)	C18B—H18D	0.9700
C8'—S1'—C2'	88.96 (13)	H12A—C12A—H12B	108.4
C2—O1—C9	122.8 (2)	C14A—C13A—C12A	110.9 (5)
C2'—N3'—C9'	110.9 (2)	C14A—C13A—H13A	109.5
C7—N15—C16B	120.8 (6)	C12A—C13A—H13A	109.5
C7—N15—C14B	122.4 (9)	C14A—C13A—H13B	109.5
C16B—N15—C14B	115.3 (11)	C12A—C13A—H13B	109.5
C7—N15—C14A	123.0 (3)	H13A—C13A—H13B	108.0
C16B—N15—C14A	115.1 (7)	N15—C14A—C13A	111.8 (4)
C7—N15—C16A	122.5 (3)	N15—C14A—H14A	109.2
C14B—N15—C16A	115.0 (10)	C13A—C14A—H14A	109.2
C14A—N15—C16A	114.4 (3)	N15—C14A—H14B	109.2
N3'—C2'—C3	121.9 (2)	C13A—C14A—H14B	109.2
N3'—C2'—S1'	115.43 (19)	H14A—C14A—H14B	107.9
C3—C2'—S1'	122.6 (2)	C17A—C16A—N15	115.9 (5)
O11—C2—O1	115.6 (3)	C17A—C16A—H16A	108.3
O11—C2—C3	126.6 (3)	N15—C16A—H16A	108.3
O1—C2—C3	117.8 (2)	C17A—C16A—H16B	108.3
C4—C3—C2	118.7 (2)	N15—C16A—H16B	108.3
C4—C3—C2'	120.8 (2)	H16A—C16A—H16B	107.4
C2—C3—C2'	120.4 (2)	C16A—C17A—C18A	116.8 (5)
C3—C4—C10	122.8 (2)	C16A—C17A—H17A	108.1
C3—C4—H4A	118.6	C18A—C17A—H17A	108.1
C10—C4—H4A	118.6	C16A—C17A—H17C	108.1
C5'—C4'—C9'	118.8 (3)	C18A—C17A—H17C	108.1
C5'—C4'—H4'A	120.6	H17A—C17A—H17C	107.3
C9'—C4'—H4'A	120.6	C17A—C18A—C8	110.3 (6)
C4'—C5'—C6'	121.2 (3)	C17A—C18A—H18A	109.6
C4'—C5'—H5'A	119.4	C8—C18A—H18A	109.6
C6'—C5'—H5'A	119.4	C17A—C18A—H18B	109.6
C6—C5—C10	122.7 (2)	C8—C18A—H18B	109.6
C6—C5—H5A	118.7	H18A—C18A—H18B	108.1
C10—C5—H5A	118.7	C13B—C12B—C6	107.4 (10)
C5—C6—C7	119.4 (2)	C13B—C12B—H12C	110.2
C5—C6—C12A	121.5 (3)	C6—C12B—H12C	110.2
C7—C6—C12A	119.0 (3)	C13B—C12B—H12D	110.2
C5—C6—C12B	120.8 (5)	C6—C12B—H12D	110.2
C7—C6—C12B	117.0 (5)	H12C—C12B—H12D	108.5
C7'—C6'—C5'	121.4 (3)	C14B—C13B—C12B	109.2 (17)
C7'—C6'—H6'A	119.3	C14B—C13B—H13C	109.8
C5'—C6'—H6'A	119.3	C12B—C13B—H13C	109.8
N15—C7—C8	120.4 (2)	C14B—C13B—H13D	109.8
N15—C7—C6	120.1 (2)	C12B—C13B—H13D	109.8
C8—C7—C6	119.5 (2)	H13C—C13B—H13D	108.3
C6'—C7'—C8'	118.2 (3)	N15—C14B—C13B	117 (2)
C6'—C7'—H7'A	120.9	N15—C14B—H14C	108.1
C8'—C7'—H7'A	120.9	C13B—C14B—H14C	108.1
C9—C8—C7	117.8 (2)	N15—C14B—H14D	108.1
C9—C8—C18B	121.0 (8)	C13B—C14B—H14D	108.1
C7—C8—C18B	120.8 (9)	H14C—C14B—H14D	107.3
C9—C8—C18A	122.1 (3)	C17B—C16B—N15	118.6 (15)
C7—C8—C18A	119.9 (3)	C17B—C16B—H16C	107.7
C7'—C8'—C9'	120.6 (3)	N15—C16B—H16C	107.7
C7'—C8'—S1'	129.7 (2)	C17B—C16B—H16D	107.7
C9'—C8'—S1'	109.7 (2)	N15—C16B—H16D	107.7
C8—C9—O1	116.6 (2)	H16C—C16B—H16D	107.1
C8—C9—C10	123.8 (2)	C16B—C17B—C18B	118.9 (17)
O1—C9—C10	119.6 (2)	C16B—C17B—H17B	107.6
N3'—C9'—C4'	125.1 (3)	C18B—C17B—H17B	107.6
N3'—C9'—C8'	115.0 (3)	C16B—C17B—H17D	107.6
C4'—C9'—C8'	119.8 (3)	C18B—C17B—H17D	107.6
C4—C10—C5	124.9 (2)	H17B—C17B—H17D	107.0
C4—C10—C9	118.3 (2)	C8—C18B—C17B	110 (2)
C5—C10—C9	116.8 (2)	C8—C18B—H18C	109.6
C6—C12A—C13A	108.3 (4)	C17B—C18B—H18C	109.6
C6—C12A—H12A	110.0	C8—C18B—H18D	109.6
C13A—C12A—H12A	110.0	C17B—C18B—H18D	109.6
C6—C12A—H12B	110.0	H18C—C18B—H18D	108.1
C13A—C12A—H12B	110.0
C9'—N3'—C2'—C3	−178.9 (2)	C2—O1—C9—C10	−1.5 (4)
C9'—N3'—C2'—S1'	0.5 (3)	C2'—N3'—C9'—C4'	−179.8 (3)
C8'—S1'—C2'—N3'	−0.6 (2)	C2'—N3'—C9'—C8'	−0.1 (3)
C8'—S1'—C2'—C3	178.8 (2)	C5'—C4'—C9'—N3'	−179.8 (3)
C9—O1—C2—O11	−175.6 (3)	C5'—C4'—C9'—C8'	0.5 (4)
C9—O1—C2—C3	3.8 (4)	C7'—C8'—C9'—N3'	178.7 (3)
O11—C2—C3—C4	175.8 (3)	S1'—C8'—C9'—N3'	−0.4 (3)
O1—C2—C3—C4	−3.6 (4)	C7'—C8'—C9'—C4'	−1.5 (4)
O11—C2—C3—C2'	−1.3 (5)	S1'—C8'—C9'—C4'	179.4 (2)
O1—C2—C3—C2'	179.2 (2)	C3—C4—C10—C5	−176.9 (3)
N3'—C2'—C3—C4	2.4 (4)	C3—C4—C10—C9	1.4 (4)
S1'—C2'—C3—C4	−177.0 (2)	C6—C5—C10—C4	178.6 (3)
N3'—C2'—C3—C2	179.5 (3)	C6—C5—C10—C9	0.4 (4)
S1'—C2'—C3—C2	0.2 (4)	C8—C9—C10—C4	−178.9 (3)
C2—C3—C4—C10	1.1 (4)	O1—C9—C10—C4	−1.2 (4)
C2'—C3—C4—C10	178.2 (2)	C8—C9—C10—C5	−0.5 (4)
C9'—C4'—C5'—C6'	0.6 (5)	O1—C9—C10—C5	177.1 (2)
C10—C5—C6—C7	−0.5 (4)	C5—C6—C12A—C13A	149.0 (4)
C10—C5—C6—C12A	175.2 (4)	C7—C6—C12A—C13A	−35.2 (6)
C10—C5—C6—C12B	−161.1 (6)	C12B—C6—C12A—C13A	54.6 (15)
C4'—C5'—C6'—C7'	−0.6 (5)	C6—C12A—C13A—C14A	57.9 (7)
C16B—N15—C7—C8	−9.6 (9)	C7—N15—C14A—C13A	21.9 (10)
C14B—N15—C7—C8	−175 (2)	C16B—N15—C14A—C13A	−146.2 (9)
C14A—N15—C7—C8	−177.0 (6)	C14B—N15—C14A—C13A	−47 (43)
C16A—N15—C7—C8	7.5 (6)	C16A—N15—C14A—C13A	−162.3 (6)
C16B—N15—C7—C6	169.1 (9)	C12A—C13A—C14A—N15	−51.8 (9)
C14B—N15—C7—C6	3 (2)	C7—N15—C16A—C17A	9.9 (8)
C14A—N15—C7—C6	1.7 (7)	C16B—N15—C16A—C17A	98 (3)
C16A—N15—C7—C6	−173.8 (5)	C14B—N15—C16A—C17A	−167 (2)
C5—C6—C7—N15	−178.0 (2)	C14A—N15—C16A—C17A	−166.0 (7)
C12A—C6—C7—N15	6.2 (5)	N15—C16A—C17A—C18A	−36.8 (10)
C12B—C6—C7—N15	−16.7 (6)	C16A—C17A—C18A—C8	44.0 (12)
C5—C6—C7—C8	0.8 (4)	C9—C8—C18A—C17A	157.9 (5)
C12A—C6—C7—C8	−175.1 (3)	C7—C8—C18A—C17A	−26.8 (12)
C12B—C6—C7—C8	162.1 (6)	C18B—C8—C18A—C17A	71 (7)
C5'—C6'—C7'—C8'	−0.4 (5)	C5—C6—C12B—C13B	−155.4 (9)
N15—C7—C8—C9	177.9 (2)	C7—C6—C12B—C13B	43.6 (12)
C6—C7—C8—C9	−0.9 (4)	C12A—C6—C12B—C13B	−57.4 (14)
N15—C7—C8—C18B	−9 (2)	C6—C12B—C13B—C14B	−57 (2)
C6—C7—C8—C18B	172 (2)	C7—N15—C14B—C13B	−20 (5)
N15—C7—C8—C18A	2.4 (8)	C16B—N15—C14B—C13B	174 (2)
C6—C7—C8—C18A	−176.4 (7)	C14A—N15—C14B—C13B	92 (46)
C6'—C7'—C8'—C9'	1.5 (4)	C16A—N15—C14B—C13B	157 (2)
C6'—C7'—C8'—S1'	−179.7 (2)	C12B—C13B—C14B—N15	48 (4)
C2'—S1'—C8'—C7'	−178.5 (3)	C7—N15—C16B—C17B	3.5 (17)
C2'—S1'—C8'—C9'	0.5 (2)	C14B—N15—C16B—C17B	170 (2)
C7—C8—C9—O1	−177.0 (2)	C14A—N15—C16B—C17B	171.8 (12)
C18B—C8—C9—O1	10 (2)	C16A—N15—C16B—C17B	−98 (4)
C18A—C8—C9—O1	−1.6 (8)	N15—C16B—C17B—C18B	21 (3)
C7—C8—C9—C10	0.8 (4)	C9—C8—C18B—C17B	−156.8 (16)
C18B—C8—C9—C10	−172 (2)	C7—C8—C18B—C17B	30 (4)
C18A—C8—C9—C10	176.2 (8)	C18A—C8—C18B—C17B	−57 (5)
C2—O1—C9—C8	176.4 (2)	C16B—C17B—C18B—C8	−36 (4)