N-(2-Benzyl­oxy­ethyl)-4,7-di­methyl-6-(1,3-di­thiol­an-2-yl)-1,2,3,4,5,6-hexahydro-1,5-methano-2-azocino­[4,3-b]­indol-2-one

The title compound, C₂₇H₃₀N₂O₂S₂, consists of a pentacyclic ring system containing a carbazolenine skeleton with an azocino group, two methyl groups and a di­thiol­ane ring as substituents.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.056
• wR factor = 0.155
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C17
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C18
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C18    -   C23      =       1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.29
           From the CIF: _reflns_number_total               2790
           Count of symmetry unique reflns         2790
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present          yes

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(2-Benzyloxyethyl)-4,7-dimethyl-6-(1,3-dithiolan-2-yl)-1,2,3,4,5,6- hexahydro-1,5-methano-2-azocino[4,3-b]indol-2-one

Crystal data

C27H30N2O2S2	F(000) = 1016
Mr = 478.65	Dx = 1.323 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.8787 (10) Å	θ = 10–18°
b = 12.446 (2) Å	µ = 0.25 mm^−1
c = 24.501 (3) Å	T = 293 K
V = 2402.5 (6) Å^3	Block, colourless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 26.3°, θmin = 2.3°
Graphite monochromator	h = 0→9
non–profiled ω scans	k = 0→15
2790 measured reflections	l = −30→0
2790 independent reflections	3 standard reflections every 120 min
1470 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0741P)^2] where P = (Fo^2 + 2Fc^2)/3
2543 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.28 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
C25	0.4252 (7)	0.4225 (8)	0.2804 (3)	0.089
H25A	0.3846	0.3591	0.2986	0.134*
H25B	0.3932	0.4848	0.3011	0.134*
H25C	0.5466	0.4194	0.2775	0.134*
S1	0.2318 (3)	0.13937 (7)	0.14345 (8)	0.0521 (5)
S2	0.0184 (2)	0.30238 (7)	0.19866 (8)	0.0535 (6)
N2	0.4933 (7)	0.5224 (4)	0.1488 (2)	0.0398 (13)
O1	0.3955 (7)	0.6168 (4)	0.2196 (2)	0.0636 (15)
C3	0.4151 (7)	0.5297 (6)	0.1972 (3)	0.0446 (17)
C1	0.5100 (6)	0.4206 (5)	0.1191 (3)	0.0382 (16)
H1	0.6096	0.4240	0.0953	0.046*
N7	0.0963 (6)	0.3344 (5)	0.0636 (2)	0.0427 (15)
C6A	0.2188 (5)	0.3402 (5)	0.1044 (2)	0.0334 (15)
C11A	0.3165 (6)	0.4302 (5)	0.0311 (3)	0.0370 (16)
O2	0.8335 (6)	0.5781 (4)	0.1151 (2)	0.0638 (15)
C7A	0.1521 (5)	0.3899 (5)	0.0188 (3)	0.0401 (17)
C5	0.3689 (5)	0.3221 (5)	0.1942 (3)	0.0415 (17)
H5	0.3881	0.2666	0.2219	0.050*
C11B	0.3523 (6)	0.3984 (5)	0.0848 (3)	0.0340 (15)
C6	0.2169 (5)	0.2843 (5)	0.1581 (3)	0.0376 (16)
C21	1.2663 (5)	0.8507 (6)	0.0552 (5)	0.079 (3)
H21	1.3247	0.9063	0.0381	0.095*
C18	1.0890 (5)	0.6877 (6)	0.1054 (3)	0.0454 (18)
C8	0.0746 (5)	0.4049 (6)	−0.0316 (3)	0.0500 (19)
H8	−0.0318	0.3761	−0.0391	0.060*
C12	0.5314 (5)	0.3291 (5)	0.1591 (3)	0.0435 (17)
H12A	0.6292	0.3419	0.1822	0.052*
H12B	0.5488	0.2622	0.1396	0.052*
C15	0.5433 (5)	0.6217 (5)	0.1209 (3)	0.0426 (17)
H15A	0.4640	0.6783	0.1304	0.051*
H15B	0.5366	0.6106	0.0817	0.051*
C20	1.2361 (6)	0.8553 (7)	0.1082 (4)	0.070 (2)
H20	1.2763	0.9133	0.1283	0.084*
C16	0.7206 (5)	0.6573 (5)	0.1355 (3)	0.0490 (19)
H16A	0.7452	0.7266	0.1191	0.059*
H16B	0.7323	0.6638	0.1748	0.059*
C19	1.1459 (5)	0.7754 (6)	0.1340 (3)	0.057 (2)
H19	1.1232	0.7809	0.1711	0.068*
C4	0.3485 (5)	0.4289 (6)	0.2241 (3)	0.0459 (18)
H4	0.2263	0.4397	0.2292	0.055*
C23	1.1234 (5)	0.6832 (6)	0.0504 (4)	0.058 (2)
H23	1.0863	0.6248	0.0299	0.069*
C17	1.0064 (5)	0.5956 (6)	0.1336 (4)	0.075 (3)
H17A	1.0724	0.5311	0.1271	0.090*
H17B	1.0057	0.6090	0.1726	0.090*
C11	0.4008 (5)	0.4895 (6)	−0.0098 (3)	0.052 (2)
H11	0.5085	0.5172	−0.0032	0.063*
C22	1.2122 (5)	0.7648 (5)	0.0256 (4)	0.069 (2)
H22	1.2354	0.7612	−0.0116	0.083*
C9	0.1605 (5)	0.4632 (7)	−0.0695 (3)	0.069 (2)
H9	0.1100	0.4753	−0.1033	0.082*
C10	0.3235 (5)	0.5064 (6)	−0.0596 (3)	0.063 (2)
H10	0.3784	0.5460	−0.0866	0.076*
C24	−0.0714 (6)	0.2839 (6)	0.0667 (3)	0.057 (2)
H24A	−0.0854	0.2511	0.1019	0.085*
H24B	−0.0810	0.2301	0.0388	0.085*
H24C	−0.1576	0.3375	0.0615	0.085*
C13	−0.0572 (5)	0.1665 (6)	0.1990 (3)	0.063 (2)
H13A	−0.1253	0.1533	0.2313	0.075*
H13B	−0.1266	0.1530	0.1671	0.075*
C14	0.0971 (5)	0.0944 (6)	0.1988 (3)	0.071 (3)
H14A	0.0637	0.0202	0.1932	0.085*
H14B	0.1569	0.0996	0.2333	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C25	0.103	0.096	0.069	−0.031	−0.025	0.001
S1	0.0547 (12)	0.0404 (10)	0.0611 (12)	−0.0012 (10)	0.0144 (11)	−0.0017 (9)
S2	0.0354 (10)	0.0622 (12)	0.0629 (12)	−0.0050 (10)	0.0183 (10)	−0.0057 (11)
N2	0.026 (3)	0.041 (3)	0.052 (3)	0.000 (3)	0.000 (3)	−0.004 (3)
O1	0.065 (4)	0.058 (3)	0.069 (4)	−0.001 (3)	0.011 (3)	−0.016 (3)
C3	0.034 (4)	0.052 (5)	0.048 (4)	−0.001 (4)	0.000 (4)	−0.007 (4)
C1	0.014 (3)	0.050 (4)	0.050 (4)	0.007 (3)	0.000 (3)	−0.004 (4)
N7	0.023 (3)	0.053 (4)	0.052 (4)	0.001 (3)	−0.008 (3)	−0.007 (3)
C6A	0.031 (3)	0.037 (4)	0.033 (3)	0.006 (3)	0.009 (3)	−0.003 (3)
C11A	0.029 (4)	0.035 (4)	0.047 (4)	0.000 (3)	0.010 (3)	−0.001 (3)
O2	0.033 (3)	0.051 (3)	0.108 (4)	−0.003 (3)	0.007 (3)	−0.007 (3)
C7A	0.037 (4)	0.042 (4)	0.041 (4)	0.000 (4)	0.007 (4)	−0.004 (3)
C5	0.031 (3)	0.048 (4)	0.045 (4)	0.002 (3)	−0.002 (3)	0.001 (4)
C11B	0.026 (3)	0.038 (4)	0.038 (4)	0.000 (3)	0.003 (3)	0.000 (3)
C6	0.028 (3)	0.039 (4)	0.045 (4)	−0.007 (3)	0.006 (3)	−0.002 (3)
C21	0.043 (5)	0.061 (6)	0.132 (9)	−0.006 (5)	0.009 (6)	0.029 (7)
C18	0.022 (3)	0.043 (4)	0.070 (5)	0.002 (3)	−0.001 (4)	0.000 (4)
C8	0.044 (4)	0.059 (5)	0.047 (5)	0.005 (4)	−0.007 (4)	0.002 (4)
C12	0.024 (3)	0.048 (4)	0.058 (4)	0.004 (3)	−0.001 (3)	−0.005 (4)
C15	0.028 (3)	0.049 (4)	0.051 (4)	0.002 (3)	−0.003 (3)	0.001 (4)
C20	0.056 (5)	0.045 (5)	0.108 (7)	−0.003 (5)	−0.015 (6)	−0.007 (5)
C16	0.033 (4)	0.045 (4)	0.068 (5)	−0.008 (4)	0.010 (4)	−0.003 (4)
C19	0.045 (4)	0.058 (5)	0.066 (5)	0.015 (4)	−0.001 (4)	−0.004 (4)
C4	0.046 (4)	0.055 (4)	0.037 (4)	−0.008 (4)	0.005 (4)	−0.010 (3)
C23	0.039 (4)	0.051 (5)	0.082 (6)	0.000 (4)	−0.010 (4)	−0.009 (5)
C17	0.032 (4)	0.061 (5)	0.133 (8)	0.004 (4)	0.005 (5)	0.027 (6)
C11	0.052 (5)	0.049 (4)	0.055 (5)	0.001 (4)	0.014 (4)	−0.005 (4)
C22	0.053 (5)	0.087 (7)	0.067 (5)	0.011 (5)	0.000 (5)	0.010 (5)
C9	0.079 (7)	0.071 (6)	0.055 (5)	0.014 (5)	−0.001 (5)	0.003 (5)
C10	0.075 (6)	0.062 (6)	0.053 (5)	0.001 (5)	0.013 (5)	0.007 (4)
C24	0.033 (4)	0.071 (6)	0.067 (5)	−0.014 (4)	−0.006 (4)	0.000 (5)
C13	0.052 (5)	0.062 (5)	0.074 (5)	−0.019 (4)	0.022 (5)	−0.003 (5)
C14	0.091 (7)	0.051 (5)	0.071 (5)	−0.013 (5)	0.019 (6)	0.004 (5)

Geometric parameters (Å, º)

C25—C4	1.508 (7)	C18—C19	1.371 (7)
C25—H25A	0.9600	C18—C23	1.377 (8)
C25—H25B	0.9600	C18—C17	1.487 (8)
C25—H25C	0.9600	C8—C9	1.359 (8)
S1—C14	1.811 (8)	C8—H8	0.9300
S1—C6	1.843 (7)	C12—H12A	0.9700
S2—C13	1.793 (8)	C12—H12B	0.9700
S2—C6	1.867 (6)	C15—C16	1.509 (7)
N2—C3	1.339 (8)	C15—H15A	0.9700
N2—C15	1.467 (8)	C15—H15B	0.9700
N2—C1	1.467 (8)	C20—C19	1.376 (8)
O1—C3	1.226 (8)	C20—H20	0.9300
C3—C4	1.511 (7)	C16—H16A	0.9700
C1—C12	1.511 (6)	C16—H16B	0.9700
C1—C11B	1.526 (8)	C19—H19	0.9300
C1—H1	0.9800	C4—H4	0.9800
N7—C7A	1.370 (8)	C23—C22	1.375 (8)
N7—C6A	1.392 (8)	C23—H23	0.9300
N7—C24	1.465 (8)	C17—H17A	0.9700
C6A—C11B	1.366 (8)	C17—H17B	0.9700
C6A—C6	1.487 (8)	C11—C10	1.380 (8)
C11A—C11B	1.401 (8)	C11—H11	0.9300
C11A—C11	1.412 (7)	C22—H22	0.9300
C11A—C7A	1.421 (7)	C9—C10	1.413 (7)
O2—C16	1.419 (8)	C9—H9	0.9300
O2—C17	1.452 (6)	C10—H10	0.9300
C7A—C8	1.390 (6)	C24—H24A	0.9600
C5—C4	1.528 (6)	C24—H24B	0.9600
C5—C12	1.544 (8)	C24—H24C	0.9600
C5—C6	1.561 (7)	C13—C14	1.512 (8)
C5—H5	0.9800	C13—H13A	0.9700
C21—C20	1.322 (8)	C13—H13B	0.9700
C21—C22	1.361 (8)	C14—H14A	0.9700
C21—H21	0.9300	C14—H14B	0.9700
C4—C25—H25A	109.5	N2—C15—C16	112.7 (6)
C4—C25—H25B	109.5	N2—C15—H15A	109.1
H25A—C25—H25B	109.5	C16—C15—H15A	109.1
C4—C25—H25C	109.5	N2—C15—H15B	109.1
H25A—C25—H25C	109.5	C16—C15—H15B	109.1
H25B—C25—H25C	109.5	H15A—C15—H15B	107.8
C14—S1—C6	96.9 (3)	C21—C20—C19	120.9 (9)
C13—S2—C6	99.6 (3)	C21—C20—H20	119.6
C3—N2—C15	118.7 (6)	C19—C20—H20	119.6
C3—N2—C1	122.5 (6)	O2—C16—C15	107.0 (5)
C15—N2—C1	118.2 (5)	O2—C16—H16A	110.3
O1—C3—N2	121.0 (7)	C15—C16—H16A	110.3
O1—C3—C4	119.6 (6)	O2—C16—H16B	110.3
N2—C3—C4	119.4 (6)	C15—C16—H16B	110.3
N2—C1—C12	109.9 (5)	H16A—C16—H16B	108.6
N2—C1—C11B	110.9 (5)	C18—C19—C20	120.6 (8)
C12—C1—C11B	108.2 (5)	C18—C19—H19	119.7
N2—C1—H1	109.3	C20—C19—H19	119.7
C12—C1—H1	109.3	C25—C4—C3	107.7 (6)
C11B—C1—H1	109.3	C25—C4—C5	110.5 (7)
C7A—N7—C6A	109.2 (5)	C3—C4—C5	118.4 (5)
C7A—N7—C24	123.2 (6)	C25—C4—H4	106.5
C6A—N7—C24	127.6 (6)	C3—C4—H4	106.5
C11B—C6A—N7	107.9 (5)	C5—C4—H4	106.5
C11B—C6A—C6	124.6 (6)	C22—C23—C18	120.2 (8)
N7—C6A—C6	127.2 (5)	C22—C23—H23	119.9
C11B—C11A—C11	136.0 (7)	C18—C23—H23	119.9
C11B—C11A—C7A	106.5 (6)	O2—C17—C18	112.5 (6)
C11—C11A—C7A	117.5 (6)	O2—C17—H17A	109.1
C16—O2—C17	111.9 (6)	C18—C17—H17A	109.1
N7—C7A—C8	129.7 (6)	O2—C17—H17B	109.1
N7—C7A—C11A	107.4 (6)	C18—C17—H17B	109.1
C8—C7A—C11A	122.8 (7)	H17A—C17—H17B	107.8
C4—C5—C12	107.8 (5)	C10—C11—C11A	120.0 (7)
C4—C5—C6	117.0 (5)	C10—C11—H11	120.0
C12—C5—C6	109.8 (5)	C11A—C11—H11	120.0
C4—C5—H5	107.3	C21—C22—C23	120.3 (8)
C12—C5—H5	107.3	C21—C22—H22	119.9
C6—C5—H5	107.3	C23—C22—H22	119.9
C6A—C11B—C11A	109.0 (6)	C8—C9—C10	122.6 (8)
C6A—C11B—C1	121.8 (6)	C8—C9—H9	118.7
C11A—C11B—C1	129.1 (6)	C10—C9—H9	118.7
C6A—C6—C5	110.6 (5)	C11—C10—C9	119.6 (8)
C6A—C6—S1	106.6 (4)	C11—C10—H10	120.2
C5—C6—S1	110.9 (4)	C9—C10—H10	120.2
C6A—C6—S2	115.0 (4)	N7—C24—H24A	109.5
C5—C6—S2	107.8 (4)	N7—C24—H24B	109.5
S1—C6—S2	106.0 (3)	H24A—C24—H24B	109.5
C20—C21—C22	120.1 (9)	N7—C24—H24C	109.5
C20—C21—H21	120.0	H24A—C24—H24C	109.5
C22—C21—H21	120.0	H24B—C24—H24C	109.5
C19—C18—C23	117.9 (7)	C14—C13—S2	107.0 (5)
C19—C18—C17	121.3 (7)	C14—C13—H13A	110.3
C23—C18—C17	120.6 (8)	S2—C13—H13A	110.3
C9—C8—C7A	117.4 (7)	C14—C13—H13B	110.3
C9—C8—H8	121.3	S2—C13—H13B	110.3
C7A—C8—H8	121.3	H13A—C13—H13B	108.6
C1—C12—C5	108.1 (5)	C13—C14—S1	106.9 (5)
C1—C12—H12A	110.1	C13—C14—H14A	110.3
C5—C12—H12A	110.1	S1—C14—H14A	110.3
C1—C12—H12B	110.1	C13—C14—H14B	110.3
C5—C12—H12B	110.1	S1—C14—H14B	110.3
H12A—C12—H12B	108.4	H14A—C14—H14B	108.6
C15—N2—C3—O1	−4.8 (10)	C14—S1—C6—C6A	−144.9 (5)
C1—N2—C3—O1	−176.2 (6)	C14—S1—C6—C5	94.7 (5)
C15—N2—C3—C4	174.5 (6)	C14—S1—C6—S2	−22.0 (4)
C1—N2—C3—C4	3.1 (9)	C13—S2—C6—C6A	115.0 (5)
C3—N2—C1—C12	−34.4 (8)	C13—S2—C6—C5	−121.1 (5)
C15—N2—C1—C12	154.3 (5)	C13—S2—C6—S1	−2.4 (4)
C3—N2—C1—C11B	85.3 (7)	N7—C7A—C8—C9	−179.3 (7)
C15—N2—C1—C11B	−86.1 (6)	C11A—C7A—C8—C9	−1.7 (11)
C7A—N7—C6A—C11B	−0.7 (7)	N2—C1—C12—C5	63.0 (6)
C24—N7—C6A—C11B	−177.3 (6)	C11B—C1—C12—C5	−58.3 (6)
C7A—N7—C6A—C6	−174.7 (6)	C4—C5—C12—C1	−60.1 (6)
C24—N7—C6A—C6	8.6 (10)	C6—C5—C12—C1	68.3 (7)
C6A—N7—C7A—C8	179.0 (7)	C3—N2—C15—C16	90.8 (7)
C24—N7—C7A—C8	−4.1 (11)	C1—N2—C15—C16	−97.5 (7)
C6A—N7—C7A—C11A	1.2 (7)	C22—C21—C20—C19	−1.8 (14)
C24—N7—C7A—C11A	178.1 (6)	C17—O2—C16—C15	−171.6 (6)
C11B—C11A—C7A—N7	−1.3 (7)	N2—C15—C16—O2	65.5 (7)
C11—C11A—C7A—N7	179.2 (6)	C23—C18—C19—C20	−0.8 (10)
C11B—C11A—C7A—C8	−179.3 (6)	C17—C18—C19—C20	173.9 (7)
C11—C11A—C7A—C8	1.2 (10)	C21—C20—C19—C18	1.7 (12)
N7—C6A—C11B—C11A	−0.2 (7)	O1—C3—C4—C25	−56.0 (9)
C6—C6A—C11B—C11A	174.0 (5)	N2—C3—C4—C25	124.7 (7)
N7—C6A—C11B—C1	180.0 (5)	O1—C3—C4—C5	177.7 (7)
C6—C6A—C11B—C1	−5.8 (9)	N2—C3—C4—C5	−1.6 (10)
C11—C11A—C11B—C6A	−179.8 (7)	C12—C5—C4—C25	−94.7 (7)
C7A—C11A—C11B—C6A	0.9 (7)	C6—C5—C4—C25	141.2 (7)
C11—C11A—C11B—C1	0.1 (13)	C12—C5—C4—C3	30.2 (8)
C7A—C11A—C11B—C1	−179.3 (6)	C6—C5—C4—C3	−93.9 (8)
N2—C1—C11B—C6A	−91.9 (7)	C19—C18—C23—C22	0.1 (11)
C12—C1—C11B—C6A	28.7 (8)	C17—C18—C23—C22	−174.6 (7)
N2—C1—C11B—C11A	88.2 (8)	C16—O2—C17—C18	−73.7 (9)
C12—C1—C11B—C11A	−151.2 (6)	C19—C18—C17—O2	119.3 (8)
C11B—C6A—C6—C5	12.9 (8)	C23—C18—C17—O2	−66.2 (9)
N7—C6A—C6—C5	−174.0 (6)	C11B—C11A—C11—C10	−179.4 (7)
C11B—C6A—C6—S1	−107.7 (6)	C7A—C11A—C11—C10	0.0 (10)
N7—C6A—C6—S1	65.4 (7)	C20—C21—C22—C23	1.1 (14)
C11B—C6A—C6—S2	135.2 (6)	C18—C23—C22—C21	−0.2 (12)
N7—C6A—C6—S2	−51.7 (7)	C7A—C8—C9—C10	1.1 (12)
C4—C5—C6—C6A	80.3 (7)	C11A—C11—C10—C9	−0.6 (11)
C12—C5—C6—C6A	−42.9 (7)	C8—C9—C10—C11	0.0 (12)
C4—C5—C6—S1	−161.7 (5)	C6—S2—C13—C14	32.3 (6)
C12—C5—C6—S1	75.1 (6)	S2—C13—C14—S1	−51.0 (7)
C4—C5—C6—S2	−46.2 (7)	C6—S1—C14—C13	45.3 (6)
C12—C5—C6—S2	−169.4 (4)