4-Ethyl-6,6-ethyl­enedithio-2-(2-methoxy­ethyl)-7-methoxy­methyl­ene-2,3,4,5,6,7-hexa­hydro-1,5-methano-1H-azocino[4,3-b]indol-3-one

In the title compound, C₂₃H₃₀N₂O₃S₂, the dithiol­ane ring adopts an envelope conformation. In the crystal structure, the mol­ecules are stacked along the b axis; dipole-dipole and van der Waals inter­actions are effective in the packing.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.181
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 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).

4-Ethyl-6,6-ethylenedithio-2-(2-methoxyethyl)-7-methoxymethylene- 2,3,4,5,6,7-hexahydro-1,5-methano-1H-azocino[4,3-b]indol-3-one

Crystal data

C23H30N2O3S2	F(000) = 952
Mr = 446.64	Dx = 1.341 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 15.897 (3) Å	θ = 3.2–34.6°
b = 7.0394 (14) Å	µ = 2.40 mm^−1
c = 21.195 (3) Å	T = 298 K
β = 111.164 (13)°	Rod, colourless
V = 2211.8 (7) Å^3	0.35 × 0.20 × 0.15 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2322 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 71.1°, θmin = 3.0°
non–profiled ω scans	h = −18→19
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
Tmin = 0.590, Tmax = 0.697	l = −26→0
4215 measured reflections	3 standard reflections every 120 reflections
4119 independent reflections	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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.181	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0876P)^2] where P = (Fo^2 + 2Fc^2)/3
3919 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.32 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
S1	0.17655 (8)	0.0249 (2)	0.92408 (6)	0.0619 (4)
S2	0.12535 (9)	0.41457 (19)	0.87060 (6)	0.0594 (4)
O1	−0.04995 (18)	0.2858 (4)	0.61863 (14)	0.0492 (8)
O2	−0.0791 (2)	0.3900 (4)	0.94719 (14)	0.0498 (8)
O3	−0.0635 (2)	−0.1310 (5)	0.54601 (17)	0.0691 (10)
N2	−0.0551 (2)	0.0178 (5)	0.67584 (15)	0.0363 (8)
N7	−0.0404 (2)	0.1377 (5)	0.88839 (15)	0.0364 (8)
C1	−0.0188 (2)	−0.0944 (6)	0.73894 (18)	0.0367 (9)
C3	−0.0178 (2)	0.1843 (6)	0.66886 (19)	0.0379 (9)
C4	0.0662 (3)	0.2533 (6)	0.72673 (19)	0.0431 (10)
C5	0.1142 (3)	0.1104 (7)	0.78544 (19)	0.0424 (10)
C6	0.0983 (3)	0.1576 (6)	0.85194 (19)	0.0404 (10)
C6a	0.0049 (2)	0.1002 (6)	0.84445 (18)	0.0346 (9)
C7a	−0.1227 (3)	0.0443 (5)	0.86514 (18)	0.0348 (9)
C8	−0.1894 (3)	0.0387 (6)	0.8920 (2)	0.0408 (10)
C9	−0.2663 (3)	−0.0653 (6)	0.8582 (2)	0.0445 (10)
C10	−0.2750 (3)	−0.1622 (6)	0.7985 (2)	0.0458 (10)
C11	−0.2086 (3)	−0.1595 (6)	0.77217 (19)	0.0413 (10)
C11a	−0.1300 (3)	−0.0549 (5)	0.80539 (18)	0.0340 (9)
C11b	−0.0482 (2)	−0.0196 (6)	0.79399 (17)	0.0325 (8)
C12	0.0837 (3)	−0.0922 (6)	0.7626 (2)	0.0441 (10)
C13	0.1325 (3)	0.3363 (9)	0.6962 (2)	0.0744 (17)
C14	0.1712 (3)	0.1902 (11)	0.6612 (3)	0.096 (2)
C15	0.2204 (4)	0.3894 (11)	0.9487 (3)	0.092 (2)
C16	0.2637 (3)	0.2018 (10)	0.9492 (3)	0.091 (2)
C17	−0.0143 (3)	0.2536 (6)	0.94934 (18)	0.0409 (10)
C18	−0.0902 (4)	0.5313 (7)	0.8976 (2)	0.0677 (15)
C19	−0.1365 (3)	−0.0511 (7)	0.62192 (19)	0.0452 (11)
C20	−0.1152 (3)	−0.2077 (7)	0.5813 (2)	0.0563 (13)
C21	−0.0237 (4)	−0.2666 (9)	0.5194 (3)	0.095 (2)
H1	−0.0398	−0.2259	0.7291	0.044*
H4	0.0465	0.3602	0.7476	0.052*
H5	0.1792	0.1178	0.7950	0.051*
H8	−0.1831	0.1029	0.9318	0.049*
H9	−0.3125	−0.0708	0.8752	0.053*
H10	−0.3276	−0.2304	0.7763	0.055*
H11A	−0.2153	−0.2259	0.7327	0.050*
H12A	0.1031	−0.1291	0.7259	0.053*
H12B	0.1093	−0.1803	0.7998	0.053*
H13A	0.1017	0.4339	0.6637	0.089*
H13B	0.1818	0.3966	0.7320	0.089*
H14A	0.2117	0.2518	0.6434	0.144*
H14B	0.1230	0.1319	0.6249	0.144*
H14C	0.2032	0.0948	0.6932	0.144*
H15A	0.2636	0.4905	0.9527	0.110*
H15B	0.2005	0.3982	0.9868	0.110*
H16A	0.3064	0.1740	0.9942	0.109*
H16B	0.2958	0.2029	0.9180	0.109*
H17A	−0.0045	0.1717	0.9882	0.049*
H17B	0.0423	0.3169	0.9553	0.049*
H18A	−0.1354	0.6201	0.8988	0.102*
H18B	−0.1085	0.4732	0.8537	0.102*
H18C	−0.0341	0.5969	0.9066	0.102*
H19A	−0.1650	0.0536	0.5921	0.054*
H19B	−0.1788	−0.0980	0.6417	0.054*
H20A	−0.0819	−0.3082	0.6112	0.068*
H20B	−0.1707	−0.2611	0.5497	0.068*
H21A	0.0106	−0.2057	0.4960	0.143*
H21B	−0.0694	−0.3451	0.4884	0.143*
H21C	0.0157	−0.3438	0.5553	0.143*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (6)	0.0918 (11)	0.0378 (6)	0.0092 (7)	0.0055 (5)	0.0140 (6)
S2	0.0631 (7)	0.0629 (9)	0.0468 (6)	−0.0240 (7)	0.0136 (5)	−0.0073 (6)
O1	0.0464 (16)	0.058 (2)	0.0406 (15)	0.0091 (15)	0.0125 (13)	0.0185 (15)
O2	0.0578 (18)	0.0440 (18)	0.0453 (16)	0.0046 (15)	0.0156 (14)	−0.0065 (15)
O3	0.100 (3)	0.063 (2)	0.067 (2)	−0.002 (2)	0.058 (2)	−0.0057 (19)
N2	0.0374 (17)	0.041 (2)	0.0296 (15)	0.0009 (16)	0.0117 (13)	0.0021 (15)
N7	0.0370 (17)	0.039 (2)	0.0328 (16)	−0.0035 (15)	0.0123 (14)	−0.0028 (15)
C1	0.040 (2)	0.038 (2)	0.0333 (19)	0.0033 (19)	0.0147 (17)	0.0048 (18)
C3	0.033 (2)	0.050 (3)	0.035 (2)	0.006 (2)	0.0180 (17)	0.002 (2)
C4	0.045 (2)	0.046 (3)	0.037 (2)	−0.002 (2)	0.0119 (18)	0.001 (2)
C5	0.034 (2)	0.059 (3)	0.036 (2)	0.000 (2)	0.0139 (17)	0.007 (2)
C6	0.035 (2)	0.052 (3)	0.0323 (19)	−0.004 (2)	0.0099 (16)	−0.0002 (19)
C6A	0.035 (2)	0.038 (2)	0.0306 (18)	0.0003 (18)	0.0118 (16)	0.0054 (18)
C7A	0.042 (2)	0.029 (2)	0.0339 (19)	0.0001 (18)	0.0139 (17)	0.0031 (17)
C8	0.046 (2)	0.040 (2)	0.040 (2)	0.001 (2)	0.0193 (18)	0.0011 (19)
C9	0.046 (2)	0.043 (3)	0.053 (2)	−0.002 (2)	0.028 (2)	0.005 (2)
C10	0.048 (2)	0.041 (3)	0.049 (2)	−0.008 (2)	0.018 (2)	−0.002 (2)
C11	0.047 (2)	0.036 (2)	0.038 (2)	−0.005 (2)	0.0127 (19)	−0.0045 (19)
C11A	0.043 (2)	0.030 (2)	0.0272 (17)	0.0008 (18)	0.0100 (16)	0.0034 (16)
C11B	0.0368 (19)	0.034 (2)	0.0265 (17)	0.0019 (17)	0.0107 (15)	−0.0002 (16)
C12	0.045 (2)	0.048 (3)	0.041 (2)	0.015 (2)	0.0172 (19)	0.010 (2)
C13	0.060 (3)	0.098 (5)	0.052 (3)	−0.031 (3)	0.005 (2)	0.020 (3)
C14	0.051 (3)	0.179 (7)	0.074 (4)	0.016 (4)	0.040 (3)	0.037 (5)
C15	0.064 (4)	0.136 (6)	0.061 (3)	−0.039 (4)	0.005 (3)	−0.015 (4)
C16	0.038 (3)	0.151 (7)	0.062 (3)	−0.007 (4)	−0.007 (2)	−0.022 (4)
C17	0.047 (2)	0.044 (3)	0.0267 (18)	0.000 (2)	0.0083 (17)	−0.0051 (18)
C18	0.086 (4)	0.054 (3)	0.051 (3)	0.018 (3)	0.010 (3)	0.002 (3)
C19	0.045 (2)	0.060 (3)	0.0310 (19)	−0.005 (2)	0.0144 (18)	−0.002 (2)
C20	0.067 (3)	0.063 (3)	0.041 (2)	−0.014 (3)	0.022 (2)	−0.010 (2)
C21	0.116 (5)	0.107 (6)	0.088 (4)	0.029 (4)	0.066 (4)	−0.002 (4)

Geometric parameters (Å, º)

S1—C16	1.794 (6)	C10—C11	1.362 (5)
S1—C6	1.840 (4)	C10—C9	1.398 (6)
S2—C15	1.803 (5)	C10—H10	0.9300
S2—C6	1.868 (5)	C11—H11A	0.9300
O1—C3	1.230 (4)	C11a—C11	1.401 (5)
O2—C17	1.397 (4)	C11a—C11b	1.429 (5)
O2—C18	1.411 (5)	C12—H12A	0.9700
O3—C21	1.374 (6)	C12—H12B	0.9700
O3—C20	1.404 (5)	C13—C14	1.522 (8)
N2—C3	1.346 (5)	C13—H13A	0.9700
N2—C19	1.466 (5)	C13—H13B	0.9700
N2—C1	1.479 (5)	C14—H14A	0.9600
N7—C17	1.456 (4)	C14—H14B	0.9600
C1—C11b	1.499 (5)	C14—H14C	0.9600
C1—C12	1.522 (5)	C15—C16	1.488 (9)
C1—H1	0.9800	C15—H15A	0.9700
C3—C4	1.529 (5)	C15—H15B	0.9700
C4—C13	1.538 (6)	C16—H16A	0.9700
C4—H4	0.9800	C16—H16B	0.9700
C5—C12	1.528 (6)	C17—H17A	0.9700
C5—C4	1.567 (5)	C17—H17B	0.9700
C5—H5	0.9800	C18—H18A	0.9600
C6—C5	1.555 (5)	C18—H18B	0.9600
C6a—C11b	1.384 (5)	C18—H18C	0.9600
C6a—N7	1.393 (4)	C19—C20	1.511 (6)
C6a—C6	1.491 (5)	C19—H19A	0.9700
C7a—C8	1.374 (5)	C19—H19B	0.9700
C7a—N7	1.386 (5)	C20—H20A	0.9700
C7a—C11a	1.414 (5)	C20—H20B	0.9700
C8—H8	0.9300	C21—H21A	0.9600
C9—C8	1.382 (5)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C16—S1—C6	96.4 (2)	C1—C12—C5	107.1 (3)
C15—S2—C6	98.7 (3)	C1—C12—H12A	110.3
C17—O2—C18	113.7 (4)	C5—C12—H12A	110.3
C21—O3—C20	113.4 (4)	C1—C12—H12B	110.3
C3—N2—C19	120.2 (3)	C5—C12—H12B	110.3
C3—N2—C1	121.4 (3)	H12A—C12—H12B	108.6
C19—N2—C1	118.3 (3)	C14—C13—C4	114.0 (5)
C7a—N7—C6a	108.8 (3)	C14—C13—H13A	108.7
C7a—N7—C17	120.8 (3)	C4—C13—H13A	108.7
C6a—N7—C17	130.4 (3)	C14—C13—H13B	108.7
N2—C1—C11b	112.8 (3)	C4—C13—H13B	108.7
N2—C1—C12	108.3 (3)	H13A—C13—H13B	107.6
C11b—C1—C12	109.7 (3)	C13—C14—H14A	109.5
N2—C1—H1	108.7	C13—C14—H14B	109.5
C11b—C1—H1	108.7	H14A—C14—H14B	109.5
C12—C1—H1	108.7	C13—C14—H14C	109.5
O1—C3—N2	122.6 (4)	H14A—C14—H14C	109.5
O1—C3—C4	118.7 (4)	H14B—C14—H14C	109.5
N2—C3—C4	118.7 (3)	C16—C15—S2	109.0 (4)
C3—C4—C13	108.4 (3)	C16—C15—H15A	109.9
C3—C4—C5	117.9 (4)	S2—C15—H15A	109.9
C13—C4—C5	111.5 (3)	C16—C15—H15B	109.9
C3—C4—H4	106.1	S2—C15—H15B	109.9
C13—C4—H4	106.1	H15A—C15—H15B	108.3
C5—C4—H4	106.1	C15—C16—S1	108.0 (4)
C12—C5—C6	110.5 (3)	C15—C16—H16A	110.1
C12—C5—C4	109.8 (3)	S1—C16—H16A	110.1
C6—C5—C4	113.0 (3)	C15—C16—H16B	110.1
C12—C5—H5	107.8	S1—C16—H16B	110.1
C6—C5—H5	107.8	H16A—C16—H16B	108.4
C4—C5—H5	107.8	O2—C17—N7	112.7 (3)
C6a—C6—C5	109.1 (3)	O2—C17—H17A	109.1
C6a—C6—S1	107.4 (3)	N7—C17—H17A	109.1
C5—C6—S1	111.2 (3)	O2—C17—H17B	109.1
C6a—C6—S2	115.4 (3)	N7—C17—H17B	109.1
C5—C6—S2	107.4 (3)	H17A—C17—H17B	107.8
S1—C6—S2	106.3 (2)	O2—C18—H18A	109.5
C11b—C6a—N7	108.3 (3)	O2—C18—H18B	109.5
C11b—C6a—C6	123.6 (4)	H18A—C18—H18B	109.5
N7—C6a—C6	127.8 (3)	O2—C18—H18C	109.5
C8—C7a—N7	129.6 (4)	H18A—C18—H18C	109.5
C8—C7a—C11a	122.0 (4)	H18B—C18—H18C	109.5
N7—C7a—C11a	108.4 (3)	N2—C19—C20	111.7 (3)
C7A—C8—C9	118.0 (4)	N2—C19—H19A	109.3
C7A—C8—H8	121.0	C20—C19—H19A	109.3
C9—C8—H8	121.0	N2—C19—H19B	109.3
C8—C9—C10	120.6 (4)	C20—C19—H19B	109.3
C8—C9—H9	119.7	H19A—C19—H19B	107.9
C10—C9—H9	119.7	O3—C20—C19	108.5 (4)
C11—C10—C9	121.7 (4)	O3—C20—H20A	110.0
C11—C10—H10	119.2	C19—C20—H20A	110.0
C9—C10—H10	119.2	O3—C20—H20B	110.0
C10—C11—C11a	119.0 (4)	C19—C20—H20B	110.0
C10—C11—H11A	120.5	H20A—C20—H20B	108.4
C11a—C11—H11A	120.5	O3—C21—H21A	109.5
C11—C11a—C7A	118.7 (3)	O3—C21—H21B	109.5
C11—C11a—C11b	135.1 (4)	H21A—C21—H21B	109.5
C7a—C11a—C11b	106.2 (3)	O3—C21—H21C	109.5
C6a—C11b—C11a	108.3 (3)	H21A—C21—H21C	109.5
C6a—C11b—C1	122.8 (3)	H21B—C21—H21C	109.5
C11a—C11b—C1	128.9 (3)
C6—S1—C16—C15	45.4 (5)	S1—C6—C5—C12	70.3 (4)
C16—S1—C6—C6a	−149.7 (3)	S2—C6—C5—C12	−173.8 (3)
C16—S1—C6—C5	91.0 (3)	C6a—C6—C5—C4	75.4 (4)
C16—S1—C6—S2	−25.6 (3)	S1—C6—C5—C4	−166.3 (3)
C15—S2—C6—C6a	122.4 (3)	S2—C6—C5—C4	−50.4 (4)
C15—S2—C6—C5	−115.7 (3)	C11b—C6a—C6—C5	15.5 (5)
C15—S2—C6—S1	3.4 (3)	N7—C6a—C6—C5	−171.5 (4)
C6—S2—C15—C16	26.4 (5)	C11b—C6a—C6—S1	−105.1 (4)
C19—N2—C3—O1	1.0 (6)	N7—C6a—C6—S1	67.8 (5)
C1—N2—C3—O1	−175.4 (4)	C11b—C6a—C6—S2	136.5 (3)
C19—N2—C3—C4	178.9 (3)	N7—C6a—C6—S2	−50.6 (5)
C1—N2—C3—C4	2.5 (5)	N7—C6a—C11b—C11A	1.4 (4)
C3—N2—C1—C11b	79.1 (4)	C6—C6a—C11b—C11A	175.6 (4)
C19—N2—C1—C11b	−97.4 (4)	N7—C6a—C11b—C1	−178.0 (3)
C3—N2—C1—C12	−42.4 (5)	C6—C6a—C11b—C1	−3.9 (6)
C19—N2—C1—C12	141.1 (3)	C11b—C6a—N7—C7a	−1.0 (4)
C3—N2—C19—C20	103.6 (4)	C6—C6a—N7—C7a	−174.8 (4)
C1—N2—C19—C20	−79.8 (4)	C11b—C6a—N7—C17	179.7 (4)
C7a—N7—C17—O2	−53.4 (5)	C6—C6a—N7—C17	5.9 (6)
C6a—N7—C17—O2	125.9 (4)	C8—C7a—C11a—C11	1.1 (6)
C18—O2—C17—N7	−66.3 (5)	N7—C7a—C11a—C11	−179.5 (3)
C21—O3—C20—C19	166.5 (4)	C8—C7a—C11a—C11b	−178.7 (4)
N2—C1—C11B—C6a	−96.9 (4)	N7—C7a—C11a—C11b	0.7 (4)
C12—C1—C11B—C6a	23.8 (5)	C8—C7a—N7—C6a	179.5 (4)
N2—C1—C11b—C11a	83.7 (5)	C11a—C7a—N7—C6a	0.1 (4)
C12—C1—C11b—C11a	−155.6 (4)	C8—C7a—N7—C17	−1.1 (6)
N2—C1—C12—C5	68.8 (4)	C11a—C7a—N7—C17	179.5 (3)
C11b—C1—C12—C5	−54.6 (4)	N7—C7a—C8—C9	179.5 (4)
O1—C3—C4—C13	−43.6 (5)	C11a—C7a—C8—C9	−1.2 (6)
N2—C3—C4—C13	138.4 (4)	C10—C9—C8—C7a	0.3 (6)
O1—C3—C4—C5	−171.4 (4)	C9—C10—C11—C11a	−0.7 (6)
N2—C3—C4—C5	10.6 (5)	C11—C10—C9—C8	0.6 (6)
C3—C4—C13—C14	−66.6 (5)	C11—C11a—C11b—C6a	178.9 (4)
C5—C4—C13—C14	64.7 (5)	C7a—C11a—C11b—C6a	−1.3 (4)
C12—C5—C4—C3	17.3 (5)	C11—C11a—C11b—C1	−1.7 (7)
C6—C5—C4—C3	−106.6 (4)	C7a—C11a—C11b—C1	178.1 (4)
C12—C5—C4—C13	−109.0 (4)	C7a—C11a—C11—C10	−0.1 (6)
C6—C5—C4—C13	127.2 (4)	C11b—C11a—C11—C10	179.6 (4)
C6—C5—C12—C1	69.9 (4)	S2—C15—C16—S1	−47.6 (5)
C4—C5—C12—C1	−55.3 (4)	N2—C19—C20—O3	−66.5 (5)
C6a—C6—C5—C12	−48.1 (4)