8-(Piperidin-1-ylsulfon­yl)quinoline

There are two independent mol­ecules in the asymmetric unit of the title compound, C₁₄H₁₆N₂O₂S. The quinoline system of each mol­ecule is planar [maximum deviation from planarity = 0.05 (2) Å], while the piperidine ring exibits a chair conformation. Inter­molecular C—H...O hydrogen bonds connect symmetry-related mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.131
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11D   ..  O2B     ..       2.68 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 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-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

8-(Piperidin-1-ylsulfonyl)quinoline

Crystal data

C14H16N2O2S	Z = 4
Mr = 276.35	F(000) = 584
Triclinic, P1	Dx = 1.398 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.2682 (7) Å	Cell parameters from 25 reflections
b = 14.319 (2) Å	θ = 5.8–26.8°
c = 14.411 (2) Å	µ = 2.19 mm^−1
α = 111.31 (2)°	T = 299 K
β = 101.49 (1)°	Prism, colourless
γ = 100.71 (1)°	0.60 × 0.60 × 0.50 mm
V = 1313.3 (3) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.063
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 3.4°
Graphite monochromator	h = −8→1
ω/2θ scans	k = −15→17
5753 measured reflections	l = −17→17
4633 independent reflections	3 standard reflections every 120 min
4440 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Only H-atom coordinates refined
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0824P)^2 + 0.6511P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4633 reflections	Δρmax = 0.51 e Å^−3
440 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0304 (15)

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
C1A	0.4903 (3)	0.28065 (14)	−0.01137 (14)	0.0301 (4)
C2A	0.6855 (3)	0.28703 (16)	0.01783 (16)	0.0377 (4)
H2A	0.731 (3)	0.254 (2)	0.061 (2)	0.045*
C3A	0.8217 (3)	0.34753 (17)	−0.00978 (17)	0.0413 (5)
H3A	0.952 (4)	0.346 (2)	0.009 (2)	0.050*
C4A	0.7614 (3)	0.40182 (17)	−0.06376 (17)	0.0392 (5)
H4A	0.851 (4)	0.445 (2)	−0.0829 (19)	0.047*
C5A	0.5614 (3)	0.39600 (14)	−0.09728 (14)	0.0315 (4)
C6A	0.4920 (3)	0.44812 (18)	−0.15720 (17)	0.0410 (5)
H6A	0.579 (4)	0.489 (2)	−0.170 (2)	0.049*
C7A	0.2978 (3)	0.43385 (19)	−0.19194 (18)	0.0433 (5)
H7A	0.243 (4)	0.466 (2)	−0.234 (2)	0.052*
C8A	0.1704 (3)	0.36765 (17)	−0.16603 (16)	0.0375 (4)
H8A	0.028 (4)	0.356 (2)	−0.1922 (19)	0.045*
C9A	0.4215 (2)	0.33293 (13)	−0.07273 (13)	0.0276 (4)
C10A	0.0036 (3)	0.10050 (17)	−0.13286 (19)	0.0421 (5)
H3	−0.047 (4)	0.154 (2)	−0.092 (2)	0.050*
H11	0.030 (4)	0.117 (2)	−0.192 (2)	0.050*
C11A	−0.1430 (3)	−0.00499 (18)	−0.1688 (2)	0.0473 (5)
H11A	−0.260 (4)	−0.008 (2)	−0.214 (2)	0.057*
H11B	−0.164 (4)	−0.012 (2)	−0.109 (2)	0.057*
C12A	−0.0624 (4)	−0.09299 (19)	−0.2241 (2)	0.0535 (6)
H12A	−0.165 (4)	−0.162 (3)	−0.249 (2)	0.064*
H12B	−0.042 (4)	−0.088 (2)	−0.285 (3)	0.064*
C13A	0.1323 (4)	−0.08575 (18)	−0.1558 (2)	0.0486 (6)
H13A	0.191 (4)	−0.136 (2)	−0.189 (2)	0.058*
H13B	0.121 (4)	−0.091 (2)	−0.092 (2)	0.058*
C14A	0.2767 (3)	0.02080 (18)	−0.1189 (2)	0.0450 (5)
H14A	0.406 (4)	0.030 (2)	−0.072 (2)	0.054*
H14B	0.301 (4)	0.026 (2)	−0.182 (2)	0.054*
N1A	0.1881 (2)	0.10247 (13)	−0.06614 (13)	0.0371 (4)
N2A	0.2261 (2)	0.31981 (13)	−0.10744 (13)	0.0332 (4)
O1A	0.4522 (2)	0.17519 (14)	0.09727 (12)	0.0514 (4)
O2A	0.2070 (2)	0.26934 (12)	0.07491 (12)	0.0460 (4)
S1A	0.32791 (7)	0.20723 (4)	0.03159 (3)	0.03388 (18)
C1B	0.2880 (3)	0.67671 (16)	0.53983 (16)	0.0361 (4)
C2B	0.3608 (3)	0.68812 (19)	0.63990 (17)	0.0445 (5)
H2B	0.399 (4)	0.757 (2)	0.695 (2)	0.053*
C3B	0.3720 (4)	0.6008 (2)	0.66135 (19)	0.0506 (6)
H3B	0.428 (4)	0.611 (2)	0.732 (2)	0.061*
C4B	0.3055 (4)	0.50297 (19)	0.58280 (18)	0.0480 (5)
H4B	0.311 (4)	0.443 (2)	0.599 (2)	0.058*
C5B	0.2328 (3)	0.48814 (16)	0.47867 (16)	0.0366 (4)
C6B	0.1665 (4)	0.38803 (18)	0.39430 (19)	0.0461 (5)
H6B	0.170 (4)	0.330 (2)	0.409 (2)	0.055*
C7B	0.1069 (4)	0.37993 (18)	0.29566 (19)	0.0471 (5)
H7B	0.060 (4)	0.316 (2)	0.238 (2)	0.056*
C8B	0.1127 (3)	0.47165 (18)	0.28054 (17)	0.0435 (5)
H8B	0.067 (4)	0.465 (2)	0.208 (2)	0.052*
C9B	0.2275 (3)	0.57593 (15)	0.45501 (15)	0.0328 (4)
C10B	0.6184 (3)	0.8354 (2)	0.5074 (2)	0.0494 (6)
H10C	0.640 (4)	0.858 (2)	0.582 (2)	0.059*
H10D	0.652 (4)	0.766 (2)	0.482 (2)	0.059*
C11B	0.7441 (4)	0.9127 (2)	0.4802 (2)	0.0514 (6)
H11C	0.721 (4)	0.977 (3)	0.510 (2)	0.062*
H11D	0.884 (4)	0.918 (2)	0.509 (2)	0.062*
C12B	0.6913 (4)	0.8791 (2)	0.3638 (2)	0.0593 (7)
H12C	0.725 (4)	0.813 (3)	0.335 (2)	0.071*
H12D	0.774 (5)	0.928 (3)	0.347 (2)	0.071*
C13B	0.4763 (4)	0.8616 (2)	0.31902 (19)	0.0548 (6)
H13C	0.435 (4)	0.834 (3)	0.247 (3)	0.066*
H13D	0.451 (4)	0.929 (3)	0.348 (2)	0.066*
C14B	0.3507 (4)	0.7841 (2)	0.34707 (17)	0.0518 (6)
H14C	0.208 (4)	0.778 (2)	0.327 (2)	0.062*
H14D	0.372 (4)	0.714 (3)	0.313 (2)	0.062*
N1B	0.4105 (3)	0.82026 (14)	0.46086 (13)	0.0383 (4)
N2B	0.1688 (3)	0.56687 (14)	0.35571 (13)	0.0390 (4)
O1B	0.3226 (3)	0.87270 (14)	0.62425 (15)	0.0693 (6)
O2B	0.0662 (3)	0.76824 (15)	0.45763 (18)	0.0670 (5)
S1B	0.25998 (8)	0.79071 (4)	0.52125 (4)	0.04275 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0319 (9)	0.0246 (9)	0.0286 (9)	0.0067 (7)	0.0062 (7)	0.0077 (7)
C2A	0.0362 (10)	0.0335 (10)	0.0383 (10)	0.0126 (8)	0.0031 (8)	0.0121 (8)
C3A	0.0266 (9)	0.0402 (11)	0.0490 (12)	0.0107 (8)	0.0077 (8)	0.0107 (9)
C4A	0.0314 (10)	0.0355 (11)	0.0478 (12)	0.0062 (8)	0.0161 (8)	0.0133 (9)
C5A	0.0326 (9)	0.0277 (9)	0.0341 (9)	0.0091 (7)	0.0137 (7)	0.0104 (7)
C6A	0.0458 (11)	0.0406 (12)	0.0480 (12)	0.0137 (9)	0.0238 (9)	0.0250 (10)
C7A	0.0500 (12)	0.0512 (13)	0.0450 (12)	0.0241 (10)	0.0190 (9)	0.0304 (10)
C8A	0.0339 (10)	0.0425 (11)	0.0380 (10)	0.0150 (8)	0.0084 (8)	0.0178 (9)
C9A	0.0295 (8)	0.0234 (9)	0.0271 (8)	0.0080 (7)	0.0083 (7)	0.0071 (7)
C10A	0.0391 (10)	0.0340 (11)	0.0494 (12)	0.0104 (9)	0.0039 (9)	0.0180 (9)
C11A	0.0393 (11)	0.0381 (12)	0.0547 (14)	0.0050 (9)	0.0030 (10)	0.0170 (10)
C12A	0.0585 (14)	0.0338 (12)	0.0483 (13)	0.0053 (10)	0.0001 (11)	0.0072 (10)
C13A	0.0596 (14)	0.0296 (11)	0.0491 (13)	0.0166 (10)	0.0091 (11)	0.0100 (10)
C14A	0.0433 (11)	0.0380 (12)	0.0537 (13)	0.0155 (9)	0.0153 (10)	0.0166 (10)
N1A	0.0354 (8)	0.0266 (8)	0.0437 (9)	0.0072 (7)	0.0052 (7)	0.0125 (7)
N2A	0.0289 (8)	0.0328 (8)	0.0373 (8)	0.0078 (6)	0.0085 (6)	0.0149 (7)
O1A	0.0567 (9)	0.0552 (10)	0.0451 (9)	0.0115 (7)	0.0027 (7)	0.0323 (8)
O2A	0.0548 (9)	0.0457 (9)	0.0412 (8)	0.0152 (7)	0.0248 (7)	0.0160 (7)
S1A	0.0390 (3)	0.0323 (3)	0.0310 (3)	0.0076 (2)	0.00858 (19)	0.0160 (2)
C1B	0.0413 (10)	0.0309 (10)	0.0415 (11)	0.0118 (8)	0.0203 (8)	0.0161 (8)
C2B	0.0531 (12)	0.0421 (12)	0.0376 (11)	0.0102 (10)	0.0186 (9)	0.0146 (9)
C3B	0.0654 (15)	0.0537 (14)	0.0377 (12)	0.0165 (11)	0.0172 (10)	0.0232 (10)
C4B	0.0647 (14)	0.0463 (13)	0.0486 (13)	0.0216 (11)	0.0238 (11)	0.0301 (11)
C5B	0.0404 (10)	0.0343 (10)	0.0426 (11)	0.0132 (8)	0.0195 (8)	0.0190 (9)
C6B	0.0588 (13)	0.0312 (11)	0.0545 (13)	0.0162 (10)	0.0229 (10)	0.0197 (10)
C7B	0.0571 (13)	0.0319 (11)	0.0456 (12)	0.0100 (9)	0.0165 (10)	0.0093 (9)
C8B	0.0474 (11)	0.0423 (12)	0.0369 (11)	0.0090 (9)	0.0105 (9)	0.0151 (9)
C9B	0.0329 (9)	0.0329 (10)	0.0378 (10)	0.0116 (8)	0.0162 (8)	0.0162 (8)
C10B	0.0468 (12)	0.0545 (14)	0.0547 (14)	0.0141 (11)	0.0104 (10)	0.0338 (12)
C11B	0.0436 (12)	0.0504 (14)	0.0659 (15)	0.0126 (10)	0.0195 (11)	0.0290 (12)
C12B	0.0785 (18)	0.0475 (15)	0.0690 (17)	0.0226 (13)	0.0448 (15)	0.0286 (13)
C13B	0.0870 (19)	0.0423 (13)	0.0363 (12)	0.0121 (12)	0.0186 (12)	0.0205 (10)
C14B	0.0698 (16)	0.0403 (13)	0.0329 (11)	0.0017 (11)	0.0053 (10)	0.0134 (9)
N1B	0.0435 (9)	0.0365 (9)	0.0349 (9)	0.0072 (7)	0.0094 (7)	0.0177 (7)
N2B	0.0462 (9)	0.0335 (9)	0.0389 (9)	0.0103 (7)	0.0121 (7)	0.0173 (7)
O1B	0.1240 (17)	0.0352 (9)	0.0575 (11)	0.0281 (10)	0.0497 (11)	0.0140 (8)
O2B	0.0507 (10)	0.0592 (11)	0.1116 (16)	0.0310 (8)	0.0307 (10)	0.0467 (11)
S1B	0.0552 (3)	0.0294 (3)	0.0526 (3)	0.0183 (2)	0.0270 (3)	0.0178 (2)

Geometric parameters (Å, º)

C1A—C2A	1.373 (3)	C1B—C2B	1.371 (3)
C1A—C9A	1.427 (3)	C1B—C9B	1.428 (3)
C1A—S1A	1.785 (2)	C1B—S1B	1.788 (2)
C2A—C3A	1.406 (3)	C2B—C3B	1.405 (3)
C2A—H2A	0.95 (3)	C2B—H2B	0.96 (3)
C3A—C4A	1.354 (3)	C3B—C4B	1.362 (4)
C3A—H3A	0.94 (3)	C3B—H3B	0.96 (3)
C4A—C5A	1.414 (3)	C4B—C5B	1.410 (3)
C4A—H4A	0.97 (3)	C4B—H4B	0.98 (3)
C5A—C6A	1.411 (3)	C5B—C6B	1.417 (3)
C5A—C9A	1.417 (3)	C5B—C9B	1.422 (3)
C6A—C7A	1.350 (3)	C6B—C7B	1.356 (3)
C6A—H6A	0.88 (3)	C6B—H6B	0.94 (3)
C7A—C8A	1.401 (3)	C7B—C8B	1.402 (3)
C7A—H7A	0.95 (3)	C7B—H7B	0.93 (3)
C8A—N2A	1.316 (3)	C8B—N2B	1.320 (3)
C8A—H8A	0.99 (2)	C8B—H8B	0.99 (3)
C9A—N2A	1.361 (2)	C9B—N2B	1.359 (3)
C10A—N1A	1.475 (3)	C10B—N1B	1.466 (3)
C10A—C11A	1.516 (3)	C10B—C11B	1.515 (3)
C10A—H3	0.97 (3)	C10B—H10C	0.97 (3)
C10A—H11	1.00 (3)	C10B—H10D	1.02 (3)
C11A—C12A	1.516 (3)	C11B—C12B	1.510 (4)
C11A—H11A	0.94 (3)	C11B—H11C	0.92 (3)
C11A—H11B	0.94 (3)	C11B—H11D	1.00 (3)
C12A—C13A	1.516 (3)	C12B—C13B	1.502 (4)
C12A—H12A	1.01 (3)	C12B—H12C	0.98 (3)
C12A—H12B	0.95 (3)	C12B—H12D	0.97 (4)
C13A—C14A	1.519 (3)	C13B—C14B	1.525 (4)
C13A—H13A	0.93 (3)	C13B—H13C	0.93 (3)
C13A—H13B	0.96 (3)	C13B—H13D	0.97 (3)
C14A—N1A	1.480 (3)	C14B—N1B	1.470 (3)
C14A—H14A	0.99 (3)	C14B—H14C	1.00 (3)
C14A—H14B	0.98 (3)	C14B—H14D	1.00 (3)
N1A—S1A	1.6107 (17)	N1B—S1B	1.6148 (18)
O1A—S1A	1.4321 (15)	O1B—S1B	1.4333 (19)
O2A—S1A	1.4350 (16)	O2B—S1B	1.425 (2)
C2A—C1A—C9A	120.54 (18)	C2B—C1B—C9B	120.45 (19)
C2A—C1A—S1A	117.97 (15)	C2B—C1B—S1B	117.57 (16)
C9A—C1A—S1A	121.49 (14)	C9B—C1B—S1B	121.89 (15)
C1A—C2A—C3A	120.54 (19)	C1B—C2B—C3B	120.8 (2)
C1A—C2A—H2A	119.9 (15)	C1B—C2B—H2B	117.8 (16)
C3A—C2A—H2A	119.4 (15)	C3B—C2B—H2B	121.3 (16)
C4A—C3A—C2A	120.05 (18)	C4B—C3B—C2B	120.2 (2)
C4A—C3A—H3A	123.3 (17)	C4B—C3B—H3B	120.5 (18)
C2A—C3A—H3A	116.6 (17)	C2B—C3B—H3B	119.3 (19)
C3A—C4A—C5A	121.39 (19)	C3B—C4B—C5B	120.7 (2)
C3A—C4A—H4A	122.2 (15)	C3B—C4B—H4B	119.3 (17)
C5A—C4A—H4A	116.4 (15)	C5B—C4B—H4B	120.0 (17)
C6A—C5A—C9A	117.66 (17)	C4B—C5B—C6B	122.6 (2)
C6A—C5A—C4A	123.05 (18)	C4B—C5B—C9B	119.89 (19)
C9A—C5A—C4A	119.26 (18)	C6B—C5B—C9B	117.51 (19)
C7A—C6A—C5A	119.8 (2)	C7B—C6B—C5B	119.4 (2)
C7A—C6A—H6A	122.6 (17)	C7B—C6B—H6B	122.4 (17)
C5A—C6A—H6A	117.5 (17)	C5B—C6B—H6B	118.1 (17)
C6A—C7A—C8A	118.33 (19)	C6B—C7B—C8B	118.5 (2)
C6A—C7A—H7A	123.1 (16)	C6B—C7B—H7B	123.1 (18)
C8A—C7A—H7A	118.5 (16)	C8B—C7B—H7B	118.4 (18)
N2A—C8A—C7A	124.81 (18)	N2B—C8B—C7B	125.0 (2)
N2A—C8A—H8A	116.4 (15)	N2B—C8B—H8B	116.8 (16)
C7A—C8A—H8A	118.7 (15)	C7B—C8B—H8B	118.2 (16)
N2A—C9A—C5A	121.99 (17)	N2B—C9B—C5B	122.47 (18)
N2A—C9A—C1A	119.89 (16)	N2B—C9B—C1B	119.71 (18)
C5A—C9A—C1A	118.11 (16)	C5B—C9B—C1B	117.83 (18)
N1A—C10A—C11A	108.56 (18)	N1B—C10B—C11B	110.23 (19)
N1A—C10A—H3	108.7 (15)	N1B—C10B—H10C	107.4 (16)
C11A—C10A—H3	108.5 (16)	C11B—C10B—H10C	112.5 (18)
N1A—C10A—H11	109.3 (14)	N1B—C10B—H10D	110.7 (16)
C11A—C10A—H11	113.3 (15)	C11B—C10B—H10D	109.5 (17)
H3—C10A—H11	108 (2)	H10C—C10B—H10D	106 (2)
C12A—C11A—C10A	111.0 (2)	C12B—C11B—C10B	110.9 (2)
C12A—C11A—H11A	110.0 (17)	C12B—C11B—H11C	108.6 (19)
C10A—C11A—H11A	109.3 (18)	C10B—C11B—H11C	107.8 (19)
C12A—C11A—H11B	108.1 (18)	C12B—C11B—H11D	110.8 (17)
C10A—C11A—H11B	107.2 (18)	C10B—C11B—H11D	108.5 (18)
H11A—C11A—H11B	111 (2)	H11C—C11B—H11D	110 (3)
C13A—C12A—C11A	111.0 (2)	C13B—C12B—C11B	110.9 (2)
C13A—C12A—H12A	114.0 (17)	C13B—C12B—H12C	109.9 (19)
C11A—C12A—H12A	108.6 (17)	C11B—C12B—H12C	106.4 (19)
C13A—C12A—H12B	108.1 (18)	C13B—C12B—H12D	113.7 (19)
C11A—C12A—H12B	108.8 (19)	C11B—C12B—H12D	110.7 (19)
H12A—C12A—H12B	106 (2)	H12C—C12B—H12D	105 (3)
C12A—C13A—C14A	111.0 (2)	C12B—C13B—C14B	112.1 (2)
C12A—C13A—H13A	113.5 (17)	C12B—C13B—H13C	113.6 (18)
C14A—C13A—H13A	107.2 (18)	C14B—C13B—H13C	104.6 (19)
C12A—C13A—H13B	112.1 (17)	C12B—C13B—H13D	106.6 (18)
C14A—C13A—H13B	103.9 (18)	C14B—C13B—H13D	109.6 (19)
H13A—C13A—H13B	109 (2)	H13C—C13B—H13D	110 (3)
N1A—C14A—C13A	108.89 (18)	N1B—C14B—C13B	108.68 (19)
N1A—C14A—H14A	110.0 (16)	N1B—C14B—H14C	105.2 (17)
C13A—C14A—H14A	114.2 (16)	C13B—C14B—H14C	114.6 (17)
N1A—C14A—H14B	111.2 (16)	N1B—C14B—H14D	110.2 (17)
C13A—C14A—H14B	105.9 (16)	C13B—C14B—H14D	108.5 (17)
H14A—C14A—H14B	107 (2)	H14C—C14B—H14D	110 (2)
C10A—N1A—C14A	113.88 (17)	C10B—N1B—C14B	114.6 (2)
C10A—N1A—S1A	122.34 (14)	C10B—N1B—S1B	117.13 (15)
C14A—N1A—S1A	118.65 (14)	C14B—N1B—S1B	121.57 (16)
C8A—N2A—C9A	117.32 (17)	C8B—N2B—C9B	117.00 (18)
O2A—S1A—O1A	118.59 (10)	O2B—S1B—O1B	118.69 (13)
O2A—S1A—N1A	108.20 (9)	O2B—S1B—N1B	107.92 (11)
O1A—S1A—N1A	106.93 (10)	O1B—S1B—N1B	106.91 (11)
O2A—S1A—C1A	108.34 (9)	O2B—S1B—C1B	108.83 (11)
O1A—S1A—C1A	104.84 (9)	O1B—S1B—C1B	104.71 (11)
N1A—S1A—C1A	109.74 (9)	N1B—S1B—C1B	109.54 (9)
C9A—C1A—C2A—C3A	1.8 (3)	C9B—C1B—C2B—C3B	−1.9 (3)
S1A—C1A—C2A—C3A	−177.19 (15)	S1B—C1B—C2B—C3B	174.80 (18)
C1A—C2A—C3A—C4A	1.3 (3)	C1B—C2B—C3B—C4B	−1.8 (4)
C2A—C3A—C4A—C5A	−2.6 (3)	C2B—C3B—C4B—C5B	2.9 (4)
C3A—C4A—C5A—C6A	−177.4 (2)	C3B—C4B—C5B—C6B	178.5 (2)
C3A—C4A—C5A—C9A	0.8 (3)	C3B—C4B—C5B—C9B	−0.4 (3)
C9A—C5A—C6A—C7A	−2.3 (3)	C4B—C5B—C6B—C7B	−177.0 (2)
C4A—C5A—C6A—C7A	175.9 (2)	C9B—C5B—C6B—C7B	1.9 (3)
C5A—C6A—C7A—C8A	0.6 (3)	C5B—C6B—C7B—C8B	−0.1 (3)
C6A—C7A—C8A—N2A	1.9 (3)	C6B—C7B—C8B—N2B	−1.4 (4)
C6A—C5A—C9A—N2A	1.8 (3)	C4B—C5B—C9B—N2B	176.44 (19)
C4A—C5A—C9A—N2A	−176.48 (17)	C6B—C5B—C9B—N2B	−2.4 (3)
C6A—C5A—C9A—C1A	−179.44 (17)	C4B—C5B—C9B—C1B	−3.1 (3)
C4A—C5A—C9A—C1A	2.3 (3)	C6B—C5B—C9B—C1B	177.96 (18)
C2A—C1A—C9A—N2A	175.25 (17)	C2B—C1B—C9B—N2B	−175.32 (19)
S1A—C1A—C9A—N2A	−5.8 (2)	S1B—C1B—C9B—N2B	8.1 (3)
C2A—C1A—C9A—C5A	−3.5 (3)	C2B—C1B—C9B—C5B	4.3 (3)
S1A—C1A—C9A—C5A	175.39 (13)	S1B—C1B—C9B—C5B	−172.28 (14)
N1A—C10A—C11A—C12A	−56.3 (3)	N1B—C10B—C11B—C12B	−54.5 (3)
C10A—C11A—C12A—C13A	55.4 (3)	C10B—C11B—C12B—C13B	54.3 (3)
C11A—C12A—C13A—C14A	−54.8 (3)	C11B—C12B—C13B—C14B	−54.9 (3)
C12A—C13A—C14A—N1A	55.2 (3)	C12B—C13B—C14B—N1B	54.5 (3)
C11A—C10A—N1A—C14A	59.8 (3)	C11B—C10B—N1B—C14B	57.5 (3)
C11A—C10A—N1A—S1A	−145.94 (17)	C11B—C10B—N1B—S1B	−150.63 (18)
C13A—C14A—N1A—C10A	−59.4 (3)	C13B—C14B—N1B—C10B	−56.6 (3)
C13A—C14A—N1A—S1A	145.35 (17)	C13B—C14B—N1B—S1B	152.90 (19)
C7A—C8A—N2A—C9A	−2.4 (3)	C7B—C8B—N2B—C9B	0.9 (3)
C5A—C9A—N2A—C8A	0.5 (3)	C5B—C9B—N2B—C8B	1.1 (3)
C1A—C9A—N2A—C8A	−178.23 (17)	C1B—C9B—N2B—C8B	−179.33 (18)
C10A—N1A—S1A—O2A	32.1 (2)	C10B—N1B—S1B—O2B	−173.62 (17)
C14A—N1A—S1A—O2A	−174.81 (16)	C14B—N1B—S1B—O2B	−23.8 (2)
C10A—N1A—S1A—O1A	160.89 (17)	C10B—N1B—S1B—O1B	57.6 (2)
C14A—N1A—S1A—O1A	−46.00 (19)	C14B—N1B—S1B—O1B	−152.53 (19)
C10A—N1A—S1A—C1A	−85.93 (19)	C10B—N1B—S1B—C1B	−55.28 (19)
C14A—N1A—S1A—C1A	67.17 (18)	C14B—N1B—S1B—C1B	94.5 (2)
C2A—C1A—S1A—O2A	131.38 (15)	C2B—C1B—S1B—O2B	−128.92 (18)
C9A—C1A—S1A—O2A	−47.57 (17)	C9B—C1B—S1B—O2B	47.74 (19)
C2A—C1A—S1A—O1A	3.84 (18)	C2B—C1B—S1B—O1B	−1.0 (2)
C9A—C1A—S1A—O1A	−175.12 (15)	C9B—C1B—S1B—O1B	175.62 (17)
C2A—C1A—S1A—N1A	−110.68 (16)	C2B—C1B—S1B—N1B	113.31 (17)
C9A—C1A—S1A—N1A	70.36 (16)	C9B—C1B—S1B—N1B	−70.03 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O2A^i	0.94 (3)	2.52 (3)	3.374 (3)	151 (2)
C11B—H11D···O2B^i	1.00 (3)	2.68 (3)	3.388 (3)	128 (2)

Symmetry code: (i) x+1, y, z.