(3R)-Meth­yl 6-tert-butoxy­carbonyl­amino-5-oxo-2,3-dihydro-5H-1,3-thia­zolo[3,2-a]pyridine-3-carboxyl­ate

The absolute configuration has been determined for the title compound, C₁₄H₁₈N₂O₅S, a bicyclic aromatic building block which can act as a rigid fluorescence marker in peptide backbones. In the crystal packing, the two independent molecules of the asymmetric unit are aligned in an antiparallel manner as dimers which are stabilized by antiparallel inter­molecular N—H...O=C hydrogen bonds. In addition, there are weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.086
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H18 N2 O5 S

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.97
           From the CIF: _reflns_number_total               7579
           Count of symmetry unique reflns         4084
           Completeness (_total/calc)            185.58%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3495
           Fraction of Friedel pairs measured     0.856
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: IPDS (Stoe & Cie, 1998); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: PLATON (Spek, 2003).

(3R)-Methyl 6-tert-butoxycarbonylamino-5-oxo- 2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyridine-3-carboxylate

Crystal data

C14H18N2O5S	F(000) = 688
Mr = 326.37	Cell parameters were determined by indexing 8000 reflections with I/sigma limit 6.0.
Monoclinic, P21	Dx = 1.344 Mg m^−3
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.9054 (8) Å	Cell parameters from 8000 reflections
b = 10.8101 (6) Å	θ = 2.7–28.0°
c = 13.6064 (9) Å	µ = 0.23 mm^−1
β = 112.957 (7)°	T = 173 K
V = 1612.4 (2) Å^3	Prism, colourless
Z = 4	0.60 × 0.48 × 0.28 mm

Data collection

Stoe IPDS diffractometer	7361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.0°, θmin = 2.7°
rotation scans	h = −15→15
27858 measured reflections	k = −14→14
7579 independent reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0708P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
7579 reflections	Δρmax = 0.33 e Å^−3
412 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Absolute structure: Flack (1983), 3605 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Special details

Experimental. Data were collected applying an imaging plate system (Stoe) with the following measurement parameters:

Detector distance [mm] 60 Phi movement mode Oscillation Phi incr. [degrees] 1.0 Number of exposures 360 Irradiation / exposure [min] 1.00

For a detailed description of the method see: Sheldrick, G·M., Paulus, E. Vertesy, L. & Hahn, F. (1995) Acta Cryst. B51, 89–98.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.22752 (3)	0.25840 (3)	1.03138 (3)	0.0325 (1)
O1	−0.05011 (8)	0.44559 (9)	0.80128 (8)	0.0295 (2)
O2	−0.42703 (10)	0.69004 (11)	0.62895 (9)	0.0392 (3)
O3	−0.30547 (9)	0.71209 (10)	0.53653 (9)	0.0344 (3)
O4	0.00867 (15)	0.08156 (15)	0.92214 (13)	0.0672 (5)
O5	−0.16482 (11)	0.15831 (11)	0.80339 (9)	0.0412 (3)
N1	−0.15225 (9)	0.37006 (9)	0.89894 (8)	0.0241 (3)
N2	−0.24271 (10)	0.59320 (10)	0.68177 (9)	0.0265 (3)
C1	−0.05474 (12)	0.28208 (11)	0.95417 (10)	0.0286 (3)
C2	−0.06395 (13)	0.25607 (15)	1.06137 (11)	0.0342 (3)
C3	−0.25116 (12)	0.36446 (12)	0.92745 (10)	0.0269 (3)
C4	−0.35033 (12)	0.43431 (12)	0.87565 (11)	0.0305 (3)
C5	−0.35142 (12)	0.51132 (12)	0.79088 (11)	0.0286 (3)
C6	−0.25207 (11)	0.51960 (11)	0.76347 (9)	0.0234 (3)
C7	−0.14396 (11)	0.44562 (11)	0.82019 (9)	0.0229 (3)
C8	−0.33389 (11)	0.66751 (11)	0.61634 (10)	0.0263 (3)
C9	−0.39788 (12)	0.78571 (12)	0.45088 (11)	0.0324 (3)
C10	−0.33418 (18)	0.8167 (2)	0.37627 (16)	0.0577 (6)
C11	−0.51023 (18)	0.70794 (18)	0.39378 (14)	0.0507 (5)
C12	−0.4277 (2)	0.90366 (16)	0.49569 (16)	0.0556 (6)
C13	−0.06532 (14)	0.16248 (14)	0.89155 (12)	0.0356 (4)
C14	−0.1831 (2)	0.04987 (17)	0.73656 (15)	0.0519 (6)
S2	0.15670 (3)	0.81479 (3)	0.41666 (3)	0.0373 (1)
O6	−0.01856 (8)	0.60551 (9)	0.63818 (8)	0.0298 (3)
O7	0.39364 (9)	0.50086 (11)	0.89124 (10)	0.0415 (3)
O8	0.25176 (9)	0.42079 (9)	0.94665 (8)	0.0309 (3)
O9	0.01261 (11)	0.49636 (10)	0.41939 (9)	0.0409 (3)
O10	−0.15369 (11)	0.59313 (11)	0.30546 (9)	0.0438 (3)
N3	0.08337 (9)	0.69942 (9)	0.54825 (8)	0.0242 (3)
N4	0.19050 (9)	0.53950 (10)	0.80220 (8)	0.0250 (3)
C15	−0.02799 (12)	0.70942 (11)	0.45200 (10)	0.0267 (3)
C16	−0.00584 (13)	0.81542 (13)	0.38688 (10)	0.0324 (3)
C17	0.18816 (12)	0.74173 (12)	0.53921 (10)	0.0284 (3)
C18	0.29757 (13)	0.72221 (13)	0.61957 (12)	0.0336 (4)
C19	0.30198 (12)	0.65395 (13)	0.70975 (11)	0.0309 (3)
C20	0.19805 (11)	0.61083 (11)	0.71865 (9)	0.0239 (3)
C21	0.07985 (11)	0.63714 (10)	0.63580 (9)	0.0227 (3)
C22	0.28858 (11)	0.48718 (11)	0.88097 (10)	0.0274 (3)
C23	0.34477 (14)	0.35861 (16)	1.03952 (13)	0.0412 (4)
C24	0.4071 (2)	0.2584 (2)	1.0007 (2)	0.0660 (7)
C25	0.4309 (2)	0.4527 (2)	1.11321 (17)	0.0680 (7)
C26	0.26729 (16)	0.30094 (19)	1.09370 (14)	0.0481 (5)
C27	−0.05140 (13)	0.58551 (12)	0.39243 (10)	0.0299 (3)
C28	−0.1866 (2)	0.48355 (18)	0.23846 (16)	0.0539 (5)
H1	0.02580	0.32170	0.96740	0.0340*
H2A	−0.02100	0.32060	1.11440	0.0410*
H2B	−0.02840	0.17440	1.08970	0.0410*
H4	−0.41840	0.43210	0.89550	0.0370*
H5	−0.42240	0.55830	0.75210	0.0340*
H10A	−0.38940	0.86480	0.31560	0.0690*
H10B	−0.31150	0.74000	0.35020	0.0690*
H10C	−0.26060	0.86530	0.41490	0.0690*
H11A	−0.48670	0.63160	0.36790	0.0610*
H11B	−0.56760	0.75450	0.33320	0.0610*
H11C	−0.54920	0.68740	0.44320	0.0610*
H12A	−0.48460	0.95350	0.43730	0.0670*
H12B	−0.35260	0.95080	0.53260	0.0670*
H12C	−0.46520	0.88300	0.54620	0.0670*
H14A	−0.22740	−0.01310	0.75910	0.0620*
H14B	−0.10380	0.01680	0.74330	0.0620*
H14C	−0.23060	0.07240	0.66200	0.0620*
H29	−0.185 (2)	0.584 (2)	0.6691 (17)	0.043 (5)*
H15	−0.09840	0.73010	0.47170	0.0320*
H16A	−0.03070	0.89540	0.40760	0.0390*
H16B	−0.05300	0.80210	0.30960	0.0390*
H18	0.37020	0.75370	0.61560	0.0400*
H19	0.37880	0.63760	0.76550	0.0370*
H24A	0.46190	0.21080	1.06180	0.0790*
H24B	0.45420	0.29660	0.96360	0.0790*
H24C	0.34530	0.20320	0.95150	0.0790*
H25A	0.48010	0.49020	1.07780	0.0820*
H25B	0.48460	0.41170	1.17900	0.0820*
H25C	0.38360	0.51720	1.13050	0.0820*
H26A	0.32040	0.26990	1.16420	0.0580*
H26B	0.21970	0.23230	1.05010	0.0580*
H26C	0.21180	0.36340	1.10170	0.0580*
H28A	−0.19560	0.41320	0.28020	0.0650*
H28B	−0.12250	0.46550	0.21220	0.0650*
H28C	−0.26390	0.49810	0.17780	0.0650*
H30	0.1195 (17)	0.5212 (16)	0.7974 (13)	0.025 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0377 (2)	0.0340 (2)	0.0305 (2)	−0.0020 (1)	0.0184 (1)	0.0063 (1)
O1	0.0235 (4)	0.0365 (4)	0.0315 (4)	0.0050 (3)	0.0141 (4)	0.0092 (4)
O2	0.0303 (5)	0.0485 (6)	0.0404 (5)	0.0145 (4)	0.0155 (4)	0.0129 (5)
O3	0.0276 (5)	0.0406 (5)	0.0345 (5)	0.0102 (4)	0.0116 (4)	0.0164 (4)
O4	0.0659 (9)	0.0535 (7)	0.0641 (9)	0.0320 (7)	0.0057 (7)	−0.0023 (7)
O5	0.0447 (6)	0.0378 (5)	0.0368 (5)	0.0074 (4)	0.0113 (5)	−0.0037 (4)
N1	0.0231 (5)	0.0255 (4)	0.0243 (5)	0.0015 (4)	0.0098 (4)	0.0029 (4)
N2	0.0225 (5)	0.0306 (5)	0.0285 (5)	0.0043 (4)	0.0123 (4)	0.0065 (4)
C1	0.0258 (5)	0.0313 (6)	0.0279 (6)	0.0033 (4)	0.0096 (5)	0.0069 (4)
C2	0.0349 (6)	0.0396 (6)	0.0262 (6)	0.0021 (6)	0.0098 (5)	0.0079 (5)
C3	0.0295 (6)	0.0281 (5)	0.0268 (5)	−0.0029 (4)	0.0151 (5)	0.0017 (4)
C4	0.0267 (6)	0.0333 (6)	0.0373 (6)	−0.0004 (5)	0.0189 (5)	0.0017 (5)
C5	0.0237 (5)	0.0297 (6)	0.0336 (6)	0.0035 (4)	0.0125 (5)	0.0027 (5)
C6	0.0227 (5)	0.0233 (5)	0.0241 (5)	0.0012 (4)	0.0089 (4)	0.0011 (4)
C7	0.0221 (5)	0.0244 (5)	0.0220 (5)	−0.0009 (4)	0.0083 (4)	−0.0006 (4)
C8	0.0244 (5)	0.0258 (5)	0.0266 (5)	0.0022 (4)	0.0076 (5)	0.0016 (4)
C9	0.0298 (6)	0.0325 (6)	0.0299 (6)	0.0072 (5)	0.0063 (5)	0.0097 (5)
C10	0.0455 (9)	0.0777 (12)	0.0546 (10)	0.0229 (9)	0.0248 (8)	0.0399 (10)
C11	0.0501 (10)	0.0496 (8)	0.0360 (8)	−0.0088 (8)	−0.0009 (7)	0.0049 (7)
C12	0.0742 (13)	0.0338 (7)	0.0464 (9)	0.0168 (8)	0.0102 (9)	0.0044 (7)
C13	0.0376 (7)	0.0351 (6)	0.0364 (7)	0.0074 (5)	0.0170 (6)	0.0057 (5)
C14	0.0704 (12)	0.0399 (8)	0.0464 (9)	0.0012 (7)	0.0240 (9)	−0.0081 (7)
S2	0.0421 (2)	0.0413 (2)	0.0336 (2)	−0.0033 (1)	0.0201 (1)	0.0099 (1)
O6	0.0219 (4)	0.0366 (5)	0.0319 (4)	0.0013 (3)	0.0116 (4)	0.0083 (4)
O7	0.0241 (5)	0.0509 (6)	0.0482 (6)	0.0075 (4)	0.0127 (5)	0.0169 (5)
O8	0.0240 (4)	0.0349 (5)	0.0295 (4)	0.0043 (3)	0.0058 (4)	0.0101 (4)
O9	0.0496 (6)	0.0305 (5)	0.0387 (5)	0.0027 (4)	0.0130 (5)	−0.0018 (4)
O10	0.0440 (6)	0.0384 (5)	0.0359 (5)	−0.0051 (4)	0.0012 (5)	−0.0033 (4)
N3	0.0236 (5)	0.0259 (4)	0.0235 (5)	0.0003 (4)	0.0095 (4)	0.0025 (4)
N4	0.0213 (5)	0.0300 (5)	0.0233 (5)	0.0007 (4)	0.0082 (4)	0.0019 (4)
C15	0.0284 (6)	0.0266 (5)	0.0234 (5)	−0.0002 (4)	0.0084 (5)	0.0027 (4)
C16	0.0389 (7)	0.0271 (5)	0.0281 (6)	−0.0014 (5)	0.0098 (5)	0.0048 (5)
C17	0.0308 (6)	0.0284 (5)	0.0300 (6)	−0.0014 (4)	0.0161 (5)	0.0022 (5)
C18	0.0263 (6)	0.0392 (7)	0.0386 (7)	−0.0052 (5)	0.0161 (6)	0.0036 (5)
C19	0.0228 (6)	0.0364 (6)	0.0315 (6)	0.0001 (5)	0.0084 (5)	0.0024 (5)
C20	0.0242 (6)	0.0251 (5)	0.0226 (5)	0.0011 (4)	0.0092 (4)	−0.0006 (4)
C21	0.0239 (5)	0.0219 (5)	0.0236 (5)	0.0005 (4)	0.0106 (5)	0.0005 (4)
C22	0.0245 (6)	0.0277 (5)	0.0288 (6)	0.0033 (4)	0.0090 (5)	0.0031 (4)
C23	0.0272 (6)	0.0466 (8)	0.0403 (8)	0.0054 (6)	0.0028 (6)	0.0209 (6)
C24	0.0533 (11)	0.0560 (10)	0.0922 (16)	0.0268 (9)	0.0322 (11)	0.0340 (11)
C25	0.0527 (12)	0.0800 (14)	0.0442 (9)	−0.0199 (10)	−0.0104 (9)	0.0215 (10)
C26	0.0380 (7)	0.0565 (9)	0.0431 (8)	0.0043 (7)	0.0086 (7)	0.0246 (7)
C27	0.0340 (6)	0.0290 (6)	0.0268 (6)	−0.0041 (5)	0.0121 (5)	0.0020 (4)
C28	0.0553 (10)	0.0468 (9)	0.0454 (9)	−0.0146 (8)	0.0041 (8)	−0.0115 (7)

Geometric parameters (Å, º)

S1—C2	1.8274 (17)	C2—H2B	0.9900
S1—C3	1.7558 (13)	C4—H4	0.9500
S2—C16	1.8158 (17)	C5—H5	0.9500
S2—C17	1.7485 (13)	C10—H10C	0.9800
O1—C7	1.2405 (17)	C10—H10A	0.9800
O2—C8	1.2111 (19)	C10—H10B	0.9800
O3—C9	1.4838 (18)	C11—H11A	0.9800
O3—C8	1.3463 (17)	C11—H11B	0.9800
O4—C13	1.195 (2)	C11—H11C	0.9800
O5—C13	1.318 (2)	C12—H12B	0.9800
O5—C14	1.447 (2)	C12—H12C	0.9800
O6—C21	1.2330 (17)	C12—H12A	0.9800
O7—C22	1.2122 (18)	C14—H14C	0.9800
O8—C23	1.478 (2)	C14—H14A	0.9800
O8—C22	1.3459 (17)	C14—H14B	0.9800
O9—C27	1.1942 (18)	C15—C16	1.5329 (19)
O10—C27	1.3289 (19)	C15—C27	1.5338 (18)
O10—C28	1.452 (2)	C17—C18	1.351 (2)
N1—C1	1.4617 (17)	C18—C19	1.415 (2)
N1—C3	1.3774 (19)	C19—C20	1.371 (2)
N1—C7	1.3811 (16)	C20—C21	1.4472 (18)
N2—C6	1.4064 (16)	C23—C25	1.513 (3)
N2—C8	1.3647 (17)	C23—C26	1.521 (3)
N2—H29	0.78 (3)	C23—C24	1.520 (3)
N3—C17	1.3786 (19)	C15—H15	1.0000
N3—C21	1.3831 (15)	C16—H16A	0.9900
N3—C15	1.4595 (17)	C16—H16B	0.9900
N4—C22	1.3623 (17)	C18—H18	0.9500
N4—C20	1.4052 (16)	C19—H19	0.9500
N4—H30	0.85 (2)	C24—H24A	0.9800
C1—C13	1.5263 (19)	C24—H24B	0.9800
C1—C2	1.531 (2)	C24—H24C	0.9800
C3—C4	1.346 (2)	C25—H25A	0.9800
C4—C5	1.4184 (19)	C25—H25B	0.9800
C5—C6	1.375 (2)	C25—H25C	0.9800
C6—C7	1.4550 (18)	C26—H26A	0.9800
C9—C10	1.523 (3)	C26—H26B	0.9800
C9—C11	1.513 (3)	C26—H26C	0.9800
C9—C12	1.514 (2)	C28—H28A	0.9800
C1—H1	1.0000	C28—H28B	0.9800
C2—H2A	0.9900	C28—H28C	0.9800
C2—S1—C3	90.63 (7)	H12B—C12—H12C	109.00
C16—S2—C17	91.59 (7)	C9—C12—H12B	109.00
C8—O3—C9	118.87 (12)	C9—C12—H12C	109.00
C13—O5—C14	117.47 (14)	O5—C14—H14A	109.00
C22—O8—C23	118.74 (12)	H14A—C14—H14B	109.00
C27—O10—C28	115.95 (14)	O5—C14—H14B	109.00
C3—N1—C7	124.90 (11)	O5—C14—H14C	109.00
C1—N1—C3	114.93 (10)	H14B—C14—H14C	109.00
C1—N1—C7	120.06 (11)	H14A—C14—H14C	109.00
C6—N2—C8	124.10 (12)	N3—C15—C27	108.89 (10)
C8—N2—H29	118.5 (16)	N3—C15—C16	105.85 (11)
C6—N2—H29	116.9 (16)	C16—C15—C27	112.59 (11)
C15—N3—C21	119.13 (11)	S2—C16—C15	106.07 (10)
C17—N3—C21	124.81 (11)	S2—C17—N3	111.73 (10)
C15—N3—C17	115.62 (10)	N3—C17—C18	119.76 (12)
C20—N4—C22	123.96 (12)	S2—C17—C18	128.50 (12)
C22—N4—H30	119.2 (11)	C17—C18—C19	118.76 (15)
C20—N4—H30	116.3 (11)	C18—C19—C20	121.62 (13)
N1—C1—C2	105.77 (12)	C19—C20—C21	120.08 (11)
N1—C1—C13	112.84 (11)	N4—C20—C19	127.06 (12)
C2—C1—C13	110.81 (11)	N4—C20—C21	112.86 (11)
S1—C2—C1	104.53 (10)	N3—C21—C20	114.81 (12)
N1—C3—C4	119.97 (12)	O6—C21—C20	124.77 (11)
S1—C3—C4	128.34 (12)	O6—C21—N3	120.39 (11)
S1—C3—N1	111.68 (10)	O7—C22—N4	124.70 (13)
C3—C4—C5	118.88 (14)	O7—C22—O8	125.25 (13)
C4—C5—C6	121.52 (13)	O8—C22—N4	110.03 (12)
N2—C6—C5	126.37 (12)	O8—C23—C25	110.43 (14)
N2—C6—C7	113.82 (12)	O8—C23—C24	109.37 (14)
C5—C6—C7	119.80 (11)	C24—C23—C26	110.30 (16)
O1—C7—C6	124.90 (11)	C25—C23—C26	109.68 (15)
N1—C7—C6	114.86 (12)	O8—C23—C26	101.95 (14)
O1—C7—N1	120.23 (12)	C24—C23—C25	114.39 (18)
O2—C8—O3	125.05 (12)	O10—C27—C15	109.33 (12)
O3—C8—N2	110.53 (12)	O9—C27—O10	125.24 (13)
O2—C8—N2	124.42 (13)	O9—C27—C15	125.44 (13)
C10—C9—C11	110.51 (14)	N3—C15—H15	110.00
C11—C9—C12	112.06 (15)	C16—C15—H15	110.00
O3—C9—C10	103.42 (13)	C27—C15—H15	110.00
O3—C9—C12	110.73 (12)	S2—C16—H16A	111.00
O3—C9—C11	109.97 (12)	S2—C16—H16B	110.00
C10—C9—C12	109.83 (14)	C15—C16—H16A	111.00
O4—C13—C1	122.44 (15)	C15—C16—H16B	111.00
O4—C13—O5	124.81 (16)	H16A—C16—H16B	109.00
O5—C13—C1	112.73 (13)	C17—C18—H18	121.00
C2—C1—H1	109.00	C19—C18—H18	121.00
N1—C1—H1	109.00	C18—C19—H19	119.00
C13—C1—H1	109.00	C20—C19—H19	119.00
S1—C2—H2B	111.00	C23—C24—H24A	109.00
C1—C2—H2B	111.00	C23—C24—H24B	109.00
C1—C2—H2A	111.00	C23—C24—H24C	109.00
H2A—C2—H2B	109.00	H24A—C24—H24B	109.00
S1—C2—H2A	111.00	H24A—C24—H24C	110.00
C5—C4—H4	121.00	H24B—C24—H24C	109.00
C3—C4—H4	121.00	C23—C25—H25A	109.00
C4—C5—H5	119.00	C23—C25—H25B	109.00
C6—C5—H5	119.00	C23—C25—H25C	109.00
C9—C10—H10C	109.00	H25A—C25—H25B	110.00
H10A—C10—H10B	109.00	H25A—C25—H25C	109.00
C9—C10—H10B	110.00	H25B—C25—H25C	109.00
H10B—C10—H10C	109.00	C23—C26—H26A	109.00
H10A—C10—H10C	109.00	C23—C26—H26B	109.00
C9—C10—H10A	109.00	C23—C26—H26C	110.00
C9—C11—H11A	109.00	H26A—C26—H26B	109.00
H11B—C11—H11C	109.00	H26A—C26—H26C	109.00
H11A—C11—H11B	109.00	H26B—C26—H26C	109.00
H11A—C11—H11C	110.00	O10—C28—H28A	109.00
C9—C11—H11C	110.00	O10—C28—H28B	109.00
C9—C11—H11B	109.00	O10—C28—H28C	109.00
C9—C12—H12A	109.00	H28A—C28—H28B	109.00
H12A—C12—H12C	109.00	H28A—C28—H28C	109.00
H12A—C12—H12B	109.00	H28B—C28—H28C	110.00
C3—S1—C2—C1	−29.62 (10)	C17—N3—C21—C20	−3.75 (16)
C2—S1—C3—N1	15.78 (10)	C15—N3—C21—C20	168.23 (10)
C2—S1—C3—C4	−165.29 (13)	C15—N3—C17—C18	−171.75 (12)
C16—S2—C17—N3	10.89 (10)	C17—N3—C21—O6	178.05 (11)
C17—S2—C16—C15	−24.31 (9)	C21—N3—C15—C16	161.86 (11)
C16—S2—C17—C18	−170.25 (14)	C17—N3—C15—C16	−25.43 (14)
C9—O3—C8—N2	174.42 (11)	C17—N3—C15—C27	95.84 (13)
C9—O3—C8—O2	−5.75 (19)	C20—N4—C22—O8	−177.60 (11)
C8—O3—C9—C12	63.42 (17)	C22—N4—C20—C19	−9.8 (2)
C8—O3—C9—C11	−60.96 (16)	C20—N4—C22—O7	3.8 (2)
C8—O3—C9—C10	−178.99 (13)	C22—N4—C20—C21	169.75 (11)
C14—O5—C13—C1	178.84 (14)	C2—C1—C13—O5	114.01 (15)
C14—O5—C13—O4	−2.7 (3)	C2—C1—C13—O4	−64.5 (2)
C22—O8—C23—C24	−65.74 (18)	N1—C1—C2—S1	35.82 (12)
C22—O8—C23—C26	177.49 (12)	N1—C1—C13—O4	177.13 (16)
C23—O8—C22—N4	−178.51 (11)	C13—C1—C2—S1	−86.78 (13)
C23—O8—C22—O7	0.08 (19)	N1—C1—C13—O5	−4.38 (19)
C22—O8—C23—C25	61.00 (18)	N1—C3—C4—C5	1.03 (19)
C28—O10—C27—C15	178.27 (14)	S1—C3—C4—C5	−177.83 (10)
C28—O10—C27—O9	−1.2 (2)	C3—C4—C5—C6	−2.5 (2)
C3—N1—C7—C6	−2.14 (17)	C4—C5—C6—N2	−179.54 (12)
C7—N1—C1—C2	156.72 (11)	C4—C5—C6—C7	1.69 (19)
C7—N1—C3—C4	1.37 (19)	C5—C6—C7—N1	0.57 (16)
C3—N1—C7—O1	178.89 (12)	C5—C6—C7—O1	179.48 (12)
C3—N1—C1—C13	94.32 (14)	N2—C6—C7—O1	0.56 (17)
C7—N1—C1—C13	−81.98 (15)	N2—C6—C7—N1	−178.35 (10)
C7—N1—C3—S1	−179.59 (9)	C27—C15—C16—S2	−87.84 (12)
C3—N1—C1—C2	−26.98 (14)	C16—C15—C27—O9	115.60 (17)
C1—N1—C7—C6	173.77 (10)	C16—C15—C27—O10	−63.87 (17)
C1—N1—C3—C4	−174.73 (12)	N3—C15—C27—O9	−1.5 (2)
C1—N1—C7—O1	−5.20 (17)	N3—C15—C16—S2	31.02 (12)
C1—N1—C3—S1	4.31 (13)	N3—C15—C27—O10	179.06 (12)
C8—N2—C6—C5	−0.6 (2)	N3—C17—C18—C19	2.5 (2)
C8—N2—C6—C7	178.23 (11)	S2—C17—C18—C19	−176.27 (11)
C6—N2—C8—O3	−170.93 (11)	C17—C18—C19—C20	−2.0 (2)
C6—N2—C8—O2	9.2 (2)	C18—C19—C20—C21	−1.4 (2)
C15—N3—C17—S2	7.23 (13)	C18—C19—C20—N4	178.11 (13)
C21—N3—C17—S2	179.46 (9)	N4—C20—C21—N3	−175.50 (10)
C21—N3—C17—C18	0.49 (19)	N4—C20—C21—O6	2.61 (17)
C15—N3—C21—O6	−9.97 (16)	C19—C20—C21—N3	4.10 (17)
C21—N3—C15—C27	−76.86 (14)	C19—C20—C21—O6	−177.79 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H29···O1	0.78 (3)	2.41 (2)	2.7458 (16)	107.7 (18)
N2—H29···O6	0.78 (3)	2.19 (3)	2.9539 (17)	167 (2)
N4—H30···O1	0.85 (2)	2.20 (2)	3.0346 (16)	170.2 (16)
N4—H30···O6	0.85 (2)	2.334 (17)	2.7114 (15)	107.5 (13)
C4—H4···O7^i	0.95	2.34	3.218 (2)	154
C5—H5···O2	0.95	2.18	2.8018 (18)	122
C11—H11C···O2	0.98	2.37	2.964 (2)	118
C12—H12C···O2	0.98	2.33	2.934 (2)	119
C16—H16A···O6^ii	0.99	2.49	3.1799 (17)	127
C16—H16A···O9^ii	0.99	2.53	3.3085 (18)	136
C16—H16B···O10	0.99	2.55	2.9290 (19)	103
C18—H18···O2^iii	0.95	2.45	3.250 (2)	142
C19—H19···O7	0.95	2.22	2.8152 (19)	120
C24—H24B···O7	0.98	2.41	2.988 (3)	117
C25—H25A···O7	0.98	2.34	2.923 (3)	117

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