Ethyl 2-(9-methyl­sulfonyl-1-oxo-2,3,4,9-tetra­hydro-1H-carbazol-2-yl)acetate

The title compound, C₁₇H₁₉NO₅S, crystallizes with two mol­ecules per asymmetric unit; these do not exhibit the same pattern of hydrogen bonds. The indole part of the carbazole skeleton is almost planar, while the cyclo­hexenone ring is twisted.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.070
• wR factor = 0.223
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           74.23
           From the CIF: _diffrn_reflns_theta_full          74.23
           From the CIF: _reflns_number_total               6359
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         6882
           Completeness (_total/calc)             92.40%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.98 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl 2-(9-methylsulfonyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetate

Crystal data

C17H19NO5S	Z = 4
Mr = 349.39	F(000) = 736
Triclinic, P1	Dx = 1.375 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.651 (1) Å	Cell parameters from 16 reflections
b = 12.320 (1) Å	θ = 20.7–42.0°
c = 16.605 (2) Å	µ = 1.95 mm^−1
α = 78.841 (7)°	T = 295 K
β = 78.02 (1)°	Prism, colorless
γ = 81.33 (1)°	0.54 × 0.48 × 0.12 mm
V = 1687.2 (3) Å^3

Data collection

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.054
non–profiled ω scans	θmax = 74.2°, θmin = 2.8°
Absorption correction: ψ scan (North et al., 1968)	h = 0→10
Tmin = 0.429, Tmax = 0.788	k = −15→15
6766 measured reflections	l = −20→20
6359 independent reflections	3 standard reflections every 120 min
4267 reflections with I > 2σ(I)	intensity decay: −7%

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.1403P)^2 + 0.2784P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.223	(Δ/σ)max = 0.014
S = 1.03	Δρmax = 0.64 e Å^−3
6359 reflections	Δρmin = −0.47 e Å^−3
443 parameters

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.

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

	x	y	z	Uiso*/Ueq
S1	−0.32112 (11)	0.02271 (9)	0.88393 (6)	0.0434 (3)
S1'	0.72350 (11)	0.42416 (9)	0.69110 (7)	0.0470 (3)
N1	−0.1843 (4)	−0.0002 (3)	0.7999 (2)	0.0413 (8)
C14	0.1727 (5)	0.3106 (3)	0.8554 (3)	0.0461 (10)
O3	0.2368 (4)	0.3163 (3)	0.9212 (2)	0.0567 (8)
C14'	0.1878 (6)	0.7465 (4)	0.7855 (3)	0.0560 (12)
O1'	0.3871 (4)	0.5457 (3)	0.7743 (2)	0.0592 (9)
N1'	0.5615 (4)	0.3864 (3)	0.6658 (2)	0.0395 (8)
O2'	0.2897 (5)	0.8020 (3)	0.7435 (3)	0.0779 (11)
O2	0.0608 (4)	0.3736 (3)	0.8362 (2)	0.0655 (9)
O1	0.0021 (4)	0.1133 (3)	0.88955 (18)	0.0588 (9)
O3'	0.1320 (5)	0.7485 (3)	0.8651 (3)	0.0787 (11)
C1'	0.4511 (4)	0.3429 (3)	0.5639 (3)	0.0402 (9)
C13	0.2620 (5)	0.2210 (3)	0.8099 (3)	0.0435 (9)
H10	0.2987	0.1594	0.8501	0.052*
H11	0.3552	0.2491	0.7731	0.052*
C4	−0.2003 (5)	−0.0615 (3)	0.7391 (2)	0.0393 (9)
C12	0.0327 (4)	0.1153 (3)	0.8145 (2)	0.0375 (8)
C16'	0.3364 (10)	0.7343 (6)	0.9435 (5)	0.114 (3)
H14'	0.2897	0.6786	0.9867	0.17*
H15'	0.3968	0.7759	0.9665	0.17*
H16'	0.4052	0.699	0.9004	0.17*
C11	0.1662 (5)	0.1774 (3)	0.7583 (3)	0.0390 (9)
C2	0.0253 (4)	0.0273 (3)	0.6936 (2)	0.0378 (8)
C15	0.1651 (7)	0.4056 (5)	0.9674 (4)	0.0715 (15)
H12	0.0537	0.3975	0.9895	0.086*
H13	0.1718	0.477	0.9308	0.086*
C9	0.1784 (5)	0.0651 (4)	0.6447 (3)	0.0514 (11)
H4	0.1571	0.1272	0.6011	0.062*
H5	0.2414	0.005	0.6185	0.062*
C10	0.2704 (5)	0.1007 (4)	0.7017 (3)	0.0478 (10)
H2	0.3582	0.1389	0.668	0.057*
H3	0.3146	0.0351	0.7359	0.057*
C11'	0.2072 (5)	0.6197 (3)	0.6800 (3)	0.0431 (9)
C2'	0.3595 (4)	0.4402 (3)	0.5921 (2)	0.0397 (9)
C9'	0.2079 (5)	0.5013 (4)	0.5690 (3)	0.0477 (10)
H5'	0.1463	0.4497	0.5558	0.057*
H4'	0.2316	0.5574	0.5198	0.057*
C5'	0.6757 (5)	0.2129 (3)	0.6020 (3)	0.0468 (10)
H9'	0.756	0.1902	0.6333	0.056*
C1	−0.0704 (4)	−0.0454 (3)	0.6731 (2)	0.0378 (8)
C8'	0.4345 (5)	0.2808 (4)	0.5049 (3)	0.0467 (10)
H6'	0.3566	0.3041	0.4722	0.056*
C6	−0.2919 (6)	−0.1830 (4)	0.6697 (3)	0.0555 (12)
H8	−0.3652	−0.2302	0.6682	0.067*
C3'	0.4253 (4)	0.4649 (3)	0.6531 (3)	0.0383 (9)
C5	−0.3127 (5)	−0.1296 (4)	0.7378 (3)	0.0518 (11)
H9	−0.3994	−0.1391	0.7812	0.062*
C4'	0.5740 (4)	0.3100 (3)	0.6102 (3)	0.0388 (9)
C3	−0.0439 (4)	0.0538 (3)	0.7692 (2)	0.0363 (8)
C10'	0.1115 (5)	0.5567 (4)	0.6407 (3)	0.0495 (10)
H3'	0.0634	0.5	0.6836	0.059*
H2'	0.0261	0.6082	0.6204	0.059*
C13'	0.1054 (5)	0.6711 (4)	0.7511 (3)	0.0525 (11)
H10'	0.0699	0.6119	0.7959	0.063*
H11'	0.0118	0.7135	0.7323	0.063*
C12'	0.3490 (5)	0.5439 (3)	0.7082 (3)	0.0415 (9)
C6'	0.6520 (5)	0.1510 (4)	0.5451 (3)	0.0527 (11)
H8'	0.7165	0.0844	0.5394	0.063*
C15'	0.2119 (8)	0.8088 (5)	0.9086 (4)	0.0861 (19)
H13'	0.2573	0.8706	0.87	0.103*
H12'	0.1358	0.8387	0.9529	0.103*
C7'	0.5345 (6)	0.1851 (4)	0.4960 (3)	0.0554 (11)
H7'	0.5245	0.1426	0.4572	0.066*
C7	−0.1639 (6)	−0.1683 (4)	0.6031 (3)	0.0543 (11)
H7	−0.1537	−0.2048	0.5579	0.065*
C8	−0.0531 (5)	−0.0998 (4)	0.6045 (3)	0.0484 (10)
H6	0.0324	−0.0897	0.5605	0.058*
C16	0.2497 (10)	0.4009 (6)	1.0359 (5)	0.113 (3)
H14	0.2404	0.3308	1.0726	0.169*
H15	0.2043	0.4604	1.0663	0.169*
H16	0.3599	0.4083	1.0136	0.169*
C17	−0.2414 (6)	−0.0549 (5)	0.9674 (3)	0.0656 (14)
H19	−0.1489	−0.0241	0.9723	0.098*
H17	−0.2121	−0.1305	0.9584	0.098*
H18	−0.319	−0.0532	1.0179	0.098*
O4'	0.7200 (4)	0.5403 (3)	0.6645 (2)	0.0646 (10)
O4	−0.3361 (4)	0.1373 (3)	0.8884 (2)	0.0646 (9)
O5	−0.4592 (3)	−0.0230 (3)	0.8765 (2)	0.0655 (10)
C17'	0.6946 (6)	0.3929 (5)	0.7987 (3)	0.0680 (14)
H19'	0.6055	0.4409	0.8221	0.102*
H18'	0.7882	0.4038	0.8172	0.102*
H17'	0.6739	0.3168	0.8165	0.102*
O5'	0.8559 (3)	0.3518 (3)	0.6568 (2)	0.0645 (9)
H1	0.112 (5)	0.241 (3)	0.722 (3)	0.046 (12)*
H1'	0.251 (6)	0.675 (3)	0.632 (2)	0.075 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0320 (5)	0.0489 (6)	0.0467 (6)	−0.0072 (4)	0.0032 (4)	−0.0112 (4)
S1'	0.0308 (5)	0.0441 (6)	0.0708 (7)	−0.0096 (4)	−0.0213 (5)	−0.0042 (5)
N1	0.0324 (16)	0.051 (2)	0.0419 (18)	−0.0181 (14)	0.0068 (13)	−0.0155 (15)
C14	0.046 (2)	0.042 (2)	0.056 (3)	−0.0160 (19)	−0.016 (2)	−0.0056 (19)
O3	0.063 (2)	0.0498 (18)	0.065 (2)	0.0009 (15)	−0.0279 (17)	−0.0164 (15)
C14'	0.046 (3)	0.047 (3)	0.074 (3)	0.004 (2)	−0.012 (2)	−0.013 (2)
O1'	0.0527 (19)	0.065 (2)	0.069 (2)	0.0044 (15)	−0.0291 (16)	−0.0223 (17)
N1'	0.0257 (15)	0.0382 (17)	0.058 (2)	−0.0051 (13)	−0.0145 (14)	−0.0081 (15)
O2'	0.080 (3)	0.062 (2)	0.093 (3)	−0.029 (2)	−0.006 (2)	−0.012 (2)
O2	0.062 (2)	0.057 (2)	0.086 (3)	0.0086 (16)	−0.0359 (19)	−0.0196 (18)
O1	0.062 (2)	0.084 (2)	0.0382 (16)	−0.0349 (17)	0.0033 (14)	−0.0202 (15)
O3'	0.065 (2)	0.099 (3)	0.081 (3)	−0.015 (2)	−0.008 (2)	−0.037 (2)
C1'	0.0296 (18)	0.043 (2)	0.047 (2)	−0.0118 (16)	−0.0046 (16)	−0.0012 (17)
C13	0.036 (2)	0.047 (2)	0.050 (2)	−0.0157 (17)	−0.0093 (18)	−0.0054 (18)
C4	0.037 (2)	0.040 (2)	0.042 (2)	−0.0084 (16)	−0.0055 (16)	−0.0072 (17)
C12	0.0334 (19)	0.041 (2)	0.039 (2)	−0.0100 (16)	−0.0013 (15)	−0.0089 (16)
C16'	0.144 (7)	0.094 (5)	0.132 (7)	−0.028 (5)	−0.068 (6)	−0.032 (5)
C11	0.0348 (19)	0.042 (2)	0.040 (2)	−0.0149 (16)	−0.0045 (16)	−0.0021 (17)
C2	0.036 (2)	0.040 (2)	0.037 (2)	−0.0101 (16)	−0.0025 (16)	−0.0062 (16)
C15	0.082 (4)	0.064 (3)	0.079 (4)	0.004 (3)	−0.028 (3)	−0.032 (3)
C9	0.048 (2)	0.066 (3)	0.039 (2)	−0.023 (2)	0.0067 (18)	−0.011 (2)
C10	0.040 (2)	0.054 (3)	0.048 (2)	−0.0201 (19)	0.0041 (18)	−0.0073 (19)
C11'	0.0333 (19)	0.039 (2)	0.057 (3)	−0.0032 (16)	−0.0141 (18)	−0.0031 (19)
C2'	0.0292 (18)	0.044 (2)	0.048 (2)	−0.0096 (16)	−0.0124 (16)	−0.0010 (18)
C9'	0.039 (2)	0.049 (2)	0.057 (3)	−0.0047 (18)	−0.0200 (19)	−0.003 (2)
C5'	0.0303 (19)	0.049 (2)	0.059 (3)	−0.0091 (17)	−0.0039 (18)	−0.005 (2)
C1	0.0368 (19)	0.039 (2)	0.038 (2)	−0.0074 (16)	−0.0063 (16)	−0.0063 (16)
C8'	0.043 (2)	0.056 (3)	0.043 (2)	−0.0126 (19)	−0.0080 (18)	−0.0068 (19)
C6	0.057 (3)	0.056 (3)	0.065 (3)	−0.018 (2)	−0.021 (2)	−0.018 (2)
C3'	0.0312 (18)	0.035 (2)	0.050 (2)	−0.0079 (15)	−0.0128 (16)	−0.0025 (17)
C5	0.043 (2)	0.052 (3)	0.064 (3)	−0.0154 (19)	−0.006 (2)	−0.013 (2)
C4'	0.0290 (18)	0.039 (2)	0.049 (2)	−0.0112 (15)	−0.0072 (16)	−0.0018 (17)
C3	0.0293 (17)	0.040 (2)	0.040 (2)	−0.0134 (15)	0.0007 (15)	−0.0079 (16)
C10'	0.031 (2)	0.050 (2)	0.068 (3)	−0.0022 (18)	−0.0183 (19)	−0.006 (2)
C13'	0.042 (2)	0.048 (3)	0.066 (3)	−0.0034 (19)	−0.014 (2)	−0.006 (2)
C12'	0.035 (2)	0.040 (2)	0.054 (2)	−0.0104 (16)	−0.0140 (18)	−0.0070 (18)
C6'	0.042 (2)	0.052 (3)	0.060 (3)	−0.0059 (19)	0.006 (2)	−0.014 (2)
C15'	0.086 (4)	0.091 (5)	0.096 (5)	−0.012 (4)	−0.014 (4)	−0.053 (4)
C7'	0.052 (3)	0.061 (3)	0.054 (3)	−0.013 (2)	0.000 (2)	−0.019 (2)
C7	0.066 (3)	0.052 (3)	0.054 (3)	−0.008 (2)	−0.020 (2)	−0.019 (2)
C8	0.052 (2)	0.051 (3)	0.044 (2)	−0.006 (2)	−0.0081 (19)	−0.0146 (19)
C16	0.142 (7)	0.108 (6)	0.116 (6)	0.008 (5)	−0.066 (5)	−0.059 (5)
C17	0.065 (3)	0.076 (3)	0.048 (3)	−0.014 (3)	−0.001 (2)	0.003 (2)
O4'	0.0473 (18)	0.0454 (18)	0.105 (3)	−0.0197 (14)	−0.0301 (18)	0.0059 (17)
O4	0.063 (2)	0.0507 (19)	0.075 (2)	0.0025 (16)	0.0029 (18)	−0.0215 (17)
O5	0.0317 (15)	0.090 (3)	0.079 (2)	−0.0266 (16)	0.0095 (15)	−0.0294 (19)
C17'	0.063 (3)	0.075 (4)	0.072 (3)	−0.004 (3)	−0.037 (3)	−0.005 (3)
O5'	0.0321 (15)	0.072 (2)	0.097 (3)	−0.0034 (15)	−0.0214 (16)	−0.0257 (19)

Geometric parameters (Å, º)

S1—O4	1.413 (3)	C9—H4	0.97
S1—O5	1.432 (3)	C9—H5	0.97
S1—N1	1.671 (3)	C10—H2	0.97
S1—C17	1.731 (5)	C10—H3	0.97
S1'—O4'	1.411 (3)	C11'—C13'	1.504 (6)
S1'—O5'	1.432 (3)	C11'—C12'	1.524 (5)
S1'—N1'	1.696 (3)	C11'—C10'	1.526 (6)
S1'—C17'	1.726 (5)	C11'—H1'	0.99 (2)
N1—C4	1.411 (5)	C2'—C3'	1.361 (5)
N1—C3	1.426 (4)	C2'—C9'	1.495 (5)
C14—O2	1.203 (5)	C9'—C10'	1.518 (6)
C14—O3	1.342 (5)	C9'—H5'	0.97
C14—C13	1.487 (6)	C9'—H4'	0.97
O3—C15	1.452 (6)	C5'—C4'	1.385 (6)
C14'—O2'	1.213 (6)	C5'—C6'	1.386 (6)
C14'—O3'	1.314 (6)	C5'—H9'	0.93
C14'—C13'	1.507 (6)	C1—C8	1.401 (5)
O1'—C12'	1.216 (5)	C8'—C7'	1.366 (6)
N1'—C4'	1.419 (5)	C8'—H6'	0.93
N1'—C3'	1.432 (5)	C6—C5	1.382 (6)
O1—C12	1.215 (4)	C6—C7	1.399 (7)
O3'—C15'	1.457 (6)	C6—H8	0.93
C1'—C8'	1.396 (6)	C3'—C12'	1.456 (6)
C1'—C4'	1.404 (5)	C5—H9	0.93
C1'—C2'	1.435 (6)	C10'—H3'	0.97
C13—C11	1.522 (5)	C10'—H2'	0.97
C13—H10	0.97	C13'—H10'	0.97
C13—H11	0.97	C13'—H11'	0.97
C4—C5	1.383 (6)	C6'—C7'	1.399 (7)
C4—C1	1.405 (5)	C6'—H8'	0.93
C12—C3	1.470 (5)	C15'—H13'	0.97
C12—C11	1.527 (5)	C15'—H12'	0.97
C16'—C15'	1.446 (9)	C7'—H7'	0.93
C16'—H14'	0.96	C7—C8	1.376 (6)
C16'—H15'	0.96	C7—H7	0.93
C16'—H16'	0.96	C8—H6	0.93
C11—C10	1.525 (6)	C16—H14	0.96
C11—H1	1.00 (4)	C16—H15	0.96
C2—C3	1.352 (5)	C16—H16	0.96
C2—C1	1.436 (5)	C17—H19	0.96
C2—C9	1.491 (5)	C17—H17	0.96
C15—C16	1.461 (8)	C17—H18	0.96
C15—H12	0.97	C17'—H19'	0.96
C15—H13	0.97	C17'—H18'	0.96
C9—C10	1.516 (6)	C17'—H17'	0.96
O4—S1—O5	118.0 (2)	C1'—C2'—C9'	129.1 (4)
O4—S1—N1	107.96 (18)	C2'—C9'—C10'	110.3 (4)
O5—S1—N1	105.94 (18)	C2'—C9'—H5'	109.6
O4—S1—C17	109.9 (3)	C10'—C9'—H5'	109.6
O5—S1—C17	109.6 (2)	C2'—C9'—H4'	109.6
N1—S1—C17	104.5 (2)	C10'—C9'—H4'	109.6
O4'—S1'—O5'	119.4 (2)	H5'—C9'—H4'	108.1
O4'—S1'—N1'	106.60 (17)	C4'—C5'—C6'	116.8 (4)
O5'—S1'—N1'	105.59 (18)	C4'—C5'—H9'	121.6
O4'—S1'—C17'	110.3 (3)	C6'—C5'—H9'	121.6
O5'—S1'—C17'	109.0 (2)	C8—C1—C4	119.6 (4)
N1'—S1'—C17'	104.8 (2)	C8—C1—C2	132.3 (4)
C4—N1—C3	107.4 (3)	C4—C1—C2	108.1 (3)
C4—N1—S1	125.8 (3)	C7'—C8'—C1'	118.9 (4)
C3—N1—S1	126.0 (3)	C7'—C8'—H6'	120.5
O2—C14—O3	122.7 (4)	C1'—C8'—H6'	120.5
O2—C14—C13	126.3 (4)	C5—C6—C7	122.0 (4)
O3—C14—C13	111.0 (4)	C5—C6—H8	119
C14—O3—C15	115.8 (4)	C7—C6—H8	119
O2'—C14'—O3'	124.1 (5)	C2'—C3'—N1'	109.7 (3)
O2'—C14'—C13'	123.7 (5)	C2'—C3'—C12'	124.2 (4)
O3'—C14'—C13'	112.1 (4)	N1'—C3'—C12'	124.9 (3)
C4'—N1'—C3'	106.4 (3)	C6—C5—C4	117.7 (4)
C4'—N1'—S1'	122.3 (3)	C6—C5—H9	121.1
C3'—N1'—S1'	121.6 (3)	C4—C5—H9	121.1
C14'—O3'—C15'	118.0 (5)	C5'—C4'—C1'	121.4 (4)
C8'—C1'—C4'	120.2 (4)	C5'—C4'—N1'	130.2 (4)
C8'—C1'—C2'	132.2 (4)	C1'—C4'—N1'	108.2 (3)
C4'—C1'—C2'	107.7 (4)	C2—C3—N1	109.5 (3)
C14—C13—C11	114.2 (3)	C2—C3—C12	122.6 (3)
C14—C13—H10	108.7	N1—C3—C12	127.4 (3)
C11—C13—H10	108.7	C9'—C10'—C11'	114.5 (3)
C14—C13—H11	108.7	C9'—C10'—H3'	108.6
C11—C13—H11	108.7	C11'—C10'—H3'	108.6
H10—C13—H11	107.6	C9'—C10'—H2'	108.6
C5—C4—C1	121.4 (4)	C11'—C10'—H2'	108.6
C5—C4—N1	131.3 (4)	H3'—C10'—H2'	107.6
C1—C4—N1	107.2 (3)	C11'—C13'—C14'	114.3 (4)
O1—C12—C3	124.8 (3)	C11'—C13'—H10'	108.7
O1—C12—C11	122.0 (4)	C14'—C13'—H10'	108.7
C3—C12—C11	113.0 (3)	C11'—C13'—H11'	108.7
C15'—C16'—H14'	109.5	C14'—C13'—H11'	108.7
C15'—C16'—H15'	109.5	H10'—C13'—H11'	107.6
H14'—C16'—H15'	109.5	O1'—C12'—C3'	123.5 (4)
C15'—C16'—H16'	109.5	O1'—C12'—C11'	121.6 (4)
H14'—C16'—H16'	109.5	C3'—C12'—C11'	114.7 (3)
H15'—C16'—H16'	109.5	C5'—C6'—C7'	122.5 (4)
C13—C11—C10	111.9 (3)	C5'—C6'—H8'	118.8
C13—C11—C12	111.0 (3)	C7'—C6'—H8'	118.8
C10—C11—C12	109.2 (3)	C16'—C15'—O3'	109.6 (5)
C13—C11—H1	111 (2)	C16'—C15'—H13'	109.8
C10—C11—H1	108 (2)	O3'—C15'—H13'	109.8
C12—C11—H1	106 (2)	C16'—C15'—H12'	109.8
C3—C2—C1	107.8 (3)	O3'—C15'—H12'	109.8
C3—C2—C9	124.0 (4)	H13'—C15'—H12'	108.2
C1—C2—C9	128.1 (4)	C8'—C7'—C6'	120.1 (4)
O3—C15—C16	108.8 (5)	C8'—C7'—H7'	120
O3—C15—H12	109.9	C6'—C7'—H7'	120
C16—C15—H12	109.9	C8—C7—C6	119.9 (4)
O3—C15—H13	109.9	C8—C7—H7	120
C16—C15—H13	109.9	C6—C7—H7	120
H12—C15—H13	108.3	C7—C8—C1	119.3 (4)
C2—C9—C10	110.1 (3)	C7—C8—H6	120.4
C2—C9—H4	109.6	C1—C8—H6	120.4
C10—C9—H4	109.6	C15—C16—H14	109.5
C2—C9—H5	109.6	C15—C16—H15	109.5
C10—C9—H5	109.6	H14—C16—H15	109.5
H4—C9—H5	108.2	C15—C16—H16	109.5
C9—C10—C11	112.1 (4)	H14—C16—H16	109.5
C9—C10—H2	109.2	H15—C16—H16	109.5
C11—C10—H2	109.2	S1—C17—H19	109.5
C9—C10—H3	109.2	S1—C17—H17	109.5
C11—C10—H3	109.2	H19—C17—H17	109.5
H2—C10—H3	107.9	S1—C17—H18	109.5
C13'—C11'—C12'	110.9 (4)	H19—C17—H18	109.5
C13'—C11'—C10'	111.8 (3)	H17—C17—H18	109.5
C12'—C11'—C10'	110.7 (3)	S1'—C17'—H19'	109.5
C13'—C11'—H1'	114 (3)	S1'—C17'—H18'	109.5
C12'—C11'—H1'	106 (3)	H19'—C17'—H18'	109.5
C10'—C11'—H1'	103 (3)	S1'—C17'—H17'	109.5
C3'—C2'—C1'	108.0 (3)	H19'—C17'—H17'	109.5
C3'—C2'—C9'	122.6 (4)	H18'—C17'—H17'	109.5
O4—S1—N1—C4	−132.5 (4)	C9'—C2'—C3'—C12'	6.7 (6)
O5—S1—N1—C4	−5.2 (4)	C4'—N1'—C3'—C2'	−1.3 (4)
C17—S1—N1—C4	110.6 (4)	S1'—N1'—C3'—C2'	145.3 (3)
O4—S1—N1—C3	35.9 (4)	C4'—N1'—C3'—C12'	166.8 (4)
O5—S1—N1—C3	163.1 (3)	S1'—N1'—C3'—C12'	−46.6 (5)
C17—S1—N1—C3	−81.1 (4)	C7—C6—C5—C4	−1.1 (7)
O2—C14—O3—C15	−1.5 (7)	C1—C4—C5—C6	1.0 (7)
C13—C14—O3—C15	176.3 (4)	N1—C4—C5—C6	−177.1 (4)
O4'—S1'—N1'—C4'	119.0 (3)	C6'—C5'—C4'—C1'	1.1 (6)
O5'—S1'—N1'—C4'	−8.9 (4)	C6'—C5'—C4'—N1'	175.6 (4)
C17'—S1'—N1'—C4'	−124.0 (3)	C8'—C1'—C4'—C5'	−3.6 (6)
O4'—S1'—N1'—C3'	−22.3 (4)	C2'—C1'—C4'—C5'	174.7 (4)
O5'—S1'—N1'—C3'	−150.2 (3)	C8'—C1'—C4'—N1'	−179.1 (3)
C17'—S1'—N1'—C3'	94.7 (4)	C2'—C1'—C4'—N1'	−0.8 (4)
O2'—C14'—O3'—C15'	−8.8 (8)	C3'—N1'—C4'—C5'	−173.8 (4)
C13'—C14'—O3'—C15'	173.7 (4)	S1'—N1'—C4'—C5'	39.9 (6)
O2—C14—C13—C11	−25.5 (6)	C3'—N1'—C4'—C1'	1.3 (4)
O3—C14—C13—C11	156.9 (4)	S1'—N1'—C4'—C1'	−145.1 (3)
C3—N1—C4—C5	178.9 (4)	C1—C2—C3—N1	0.2 (5)
S1—N1—C4—C5	−11.0 (7)	C9—C2—C3—N1	−177.2 (4)
C3—N1—C4—C1	0.6 (4)	C1—C2—C3—C12	172.0 (3)
S1—N1—C4—C1	170.7 (3)	C9—C2—C3—C12	−5.4 (6)
C14—C13—C11—C10	170.2 (3)	C4—N1—C3—C2	−0.5 (5)
C14—C13—C11—C12	−67.5 (5)	S1—N1—C3—C2	−170.6 (3)
O1—C12—C11—C13	6.9 (6)	C4—N1—C3—C12	−171.8 (4)
C3—C12—C11—C13	−169.1 (3)	S1—N1—C3—C12	18.1 (6)
O1—C12—C11—C10	130.7 (4)	O1—C12—C3—C2	−157.2 (4)
C3—C12—C11—C10	−45.3 (5)	C11—C12—C3—C2	18.7 (5)
C14—O3—C15—C16	−179.2 (5)	O1—C12—C3—N1	13.1 (7)
C3—C2—C9—C10	19.5 (6)	C11—C12—C3—N1	−171.1 (4)
C1—C2—C9—C10	−157.4 (4)	C2'—C9'—C10'—C11'	46.3 (5)
C2—C9—C10—C11	−47.4 (5)	C13'—C11'—C10'—C9'	−179.2 (4)
C13—C11—C10—C9	−175.0 (3)	C12'—C11'—C10'—C9'	−55.0 (5)
C12—C11—C10—C9	61.7 (5)	C12'—C11'—C13'—C14'	63.3 (5)
C8'—C1'—C2'—C3'	178.1 (4)	C10'—C11'—C13'—C14'	−172.6 (4)
C4'—C1'—C2'—C3'	0.0 (4)	O2'—C14'—C13'—C11'	31.8 (6)
C8'—C1'—C2'—C9'	4.4 (7)	O3'—C14'—C13'—C11'	−150.7 (4)
C4'—C1'—C2'—C9'	−173.6 (4)	C2'—C3'—C12'—O1'	160.9 (4)
C3'—C2'—C9'—C10'	−22.0 (5)	N1'—C3'—C12'—O1'	−5.5 (6)
C1'—C2'—C9'—C10'	150.8 (4)	C2'—C3'—C12'—C11'	−14.5 (6)
C5—C4—C1—C8	−0.5 (6)	N1'—C3'—C12'—C11'	179.1 (3)
N1—C4—C1—C8	178.0 (4)	C13'—C11'—C12'—O1'	−13.8 (6)
C5—C4—C1—C2	−179.0 (4)	C10'—C11'—C12'—O1'	−138.4 (4)
N1—C4—C1—C2	−0.4 (4)	C13'—C11'—C12'—C3'	161.7 (3)
C3—C2—C1—C8	−178.1 (4)	C10'—C11'—C12'—C3'	37.1 (5)
C9—C2—C1—C8	−0.8 (7)	C4'—C5'—C6'—C7'	1.7 (6)
C3—C2—C1—C4	0.2 (5)	C14'—O3'—C15'—C16'	−90.0 (7)
C9—C2—C1—C4	177.4 (4)	C1'—C8'—C7'—C6'	−0.4 (7)
C4'—C1'—C8'—C7'	3.1 (6)	C5'—C6'—C7'—C8'	−2.1 (7)
C2'—C1'—C8'—C7'	−174.7 (4)	C5—C6—C7—C8	0.7 (7)
C1'—C2'—C3'—N1'	0.8 (4)	C6—C7—C8—C1	−0.1 (7)
C9'—C2'—C3'—N1'	174.9 (4)	C4—C1—C8—C7	0.0 (6)
C1'—C2'—C3'—C12'	−167.4 (4)	C2—C1—C8—C7	178.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H9···O5	0.93	2.27	2.845 (6)	120
C5′—H9′···O5′	0.93	2.42	2.866 (6)	109
C17—H19···O1	0.96	2.34	3.091 (7)	134
C17′—H19′···O1′	0.96	2.32	3.075 (7)	135
C17′—H17′···O4^i	0.96	2.31	3.237 (7)	164
C17—H18···O5^ii	0.96	2.52	3.433 (6)	159
C17′—H18′···O2^i	0.96	2.40	3.314 (7)	158

Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y, −z+2.