3-Methoxy-1-(4-methoxy­phenyl)-4,4-bis­(methyl­sulfoxy)­azetidin-2-one

The title compound, C₁₃H₁₇NO₇S₂, was designed as a precursor of human leukocyte elastase inhibitors. The title compound belongs to a series of monocyclic C-methylthiol­ated β-lactam sulfones with different substituents at the ring N atom and the C atom opposite. The compound crystallizes with two independent molecules in the asymmetric unit differing mainly in the orientation of the phenyl ring.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.115
• Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           67.21
         From the CIF: _reflns_number_total               4996
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5981
         Completeness (_total/calc)             83.53%
          Alert A: < 85% complete (theta max?)

Author response: It is extremely difficult to get complete, or nearly complete, coverage of triclinic crystals when using our CCD detector with CuKa radiation. The advantage of using the CCD with CuKa is that the fraction of observed reflectiuons reletive to the total number of reflections is usually high (i.e. 4587 observed / 4996 total ~ 92%).

 Alert Level C:



PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      34.00 A   3


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-Methoxy-1-(4-methoxyphenyl)-4,4-bis(methylsulfoxy)azetidin-2-one

Crystal data

C13H17NO7S2	Z = 4
Mr = 363.40	F(000) = 760
Triclinic, P1	Dx = 1.444 Mg m^−3
a = 8.0552 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.6680 (1) Å	Cell parameters from 7139 reflections
c = 18.3257 (2) Å	θ = 2.5–67.1°
α = 95.079 (1)°	µ = 3.21 mm^−1
β = 102.171 (1)°	T = 193 K
γ = 93.226 (1)°	Prism, colorless
V = 1672.10 (3) Å^3	0.26 × 0.11 × 0.10 mm

Data collection

Bruker SMART 6000 CCD diffractometer	4996 independent reflections
Radiation source: rotating anode	4587 reflections with I > 2σ(I)
Gobel optics monochromator	Rint = 0.033
ω scans	θmax = 67.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→8
Tmin = 0.452, Tmax = 0.729	k = −13→12
8699 measured reflections	l = −21→21

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 0.2601P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
4996 reflections	Δρmax = 0.25 e Å^−3
422 parameters	Δρmin = −0.34 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: 0.0136 (7)

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
N1	0.9487 (2)	0.99549 (14)	0.32328 (9)	0.0420 (4)
C1'	0.8802 (2)	1.05737 (17)	0.37963 (11)	0.0432 (4)
C2'	0.8689 (3)	1.1751 (2)	0.37845 (13)	0.0574 (5)
H2'A	0.9095	1.2133	0.3426	0.069*
C3'	0.7977 (4)	1.2355 (2)	0.43028 (15)	0.0638 (6)
H3'A	0.7916	1.3148	0.4298	0.077*
C4'	0.7345 (3)	1.1787 (2)	0.48344 (12)	0.0516 (5)
O4'	0.6590 (2)	1.24615 (16)	0.52927 (10)	0.0680 (5)
C4'A	0.5934 (4)	1.1937 (3)	0.58554 (17)	0.0773 (8)
H4'A	0.5437	1.2506	0.6136	0.116*
H4'B	0.6841	1.1621	0.6187	0.116*
H4'C	0.5082	1.1331	0.5623	0.116*
C5'	0.7498 (3)	1.0620 (2)	0.48579 (12)	0.0545 (5)
H5'A	0.7102	1.0238	0.5220	0.065*
C6'	0.8243 (3)	1.00150 (19)	0.43413 (12)	0.0508 (5)
H6'A	0.8366	0.9230	0.4363	0.061*
C2	1.1046 (2)	1.00608 (17)	0.30416 (12)	0.0450 (4)
O2	1.2372 (2)	1.05647 (15)	0.33641 (10)	0.0633 (4)
C3	1.0379 (3)	0.93327 (18)	0.22897 (12)	0.0443 (4)
H3	1.012 (3)	0.981 (2)	0.1876 (14)	0.053*
O3	1.12763 (19)	0.84222 (14)	0.21118 (9)	0.0568 (4)
C3A	1.1268 (5)	0.8213 (3)	0.13296 (17)	0.0885 (10)
H3AA	1.1916	0.7566	0.1249	0.133*
H3AB	1.1766	0.8884	0.1165	0.133*
H3AC	1.0116	0.8049	0.1050	0.133*
C4	0.8703 (2)	0.91198 (16)	0.26045 (10)	0.0399 (4)
S1	0.68230 (6)	0.95737 (5)	0.19885 (3)	0.05078 (17)
O1A	0.7331 (2)	1.06814 (16)	0.17915 (11)	0.0707 (5)
O1B	0.6292 (2)	0.86569 (18)	0.14054 (10)	0.0775 (5)
C1C	0.5244 (3)	0.9766 (3)	0.25076 (17)	0.0724 (7)
H1CA	0.4243	1.0005	0.2191	0.109*
H1CB	0.5655	1.0345	0.2922	0.109*
H1CC	0.4970	0.9051	0.2694	0.109*
S2	0.83851 (6)	0.76776 (4)	0.29175 (3)	0.04722 (17)
O2A	0.6774 (2)	0.76282 (15)	0.31278 (11)	0.0667 (5)
O2B	0.9887 (2)	0.75806 (14)	0.34767 (10)	0.0640 (4)
C2C	0.8284 (3)	0.6638 (2)	0.21549 (16)	0.0658 (6)
H2CA	0.8120	0.5882	0.2309	0.099*
H2CB	0.9328	0.6701	0.1982	0.099*
H2CC	0.7349	0.6763	0.1756	0.099*
N11	0.4266 (2)	0.37977 (15)	0.21815 (9)	0.0439 (4)
C11'	0.3658 (2)	0.40650 (17)	0.28522 (11)	0.0436 (4)
C12'	0.3898 (3)	0.3309 (2)	0.33909 (13)	0.0584 (6)
H12A	0.4458	0.2647	0.3315	0.070*
C13'	0.3317 (4)	0.3519 (2)	0.40448 (14)	0.0644 (6)
H13A	0.3502	0.3009	0.4411	0.077*
C14'	0.2463 (3)	0.4488 (2)	0.41511 (13)	0.0560 (5)
O14'	0.1820 (3)	0.47746 (18)	0.47628 (10)	0.0798 (6)
C14A	0.2169 (5)	0.4099 (3)	0.53760 (16)	0.0908 (10)
H14A	0.1620	0.4393	0.5762	0.136*
H14B	0.3377	0.4134	0.5571	0.136*
H14C	0.1748	0.3313	0.5210	0.136*
C15'	0.2202 (3)	0.5241 (2)	0.36033 (14)	0.0620 (6)
H15A	0.1605	0.5888	0.3670	0.074*
C16'	0.2815 (3)	0.5046 (2)	0.29606 (13)	0.0560 (5)
H16A	0.2663	0.5569	0.2602	0.067*
C12	0.5869 (3)	0.35633 (18)	0.20864 (12)	0.0460 (5)
O12	0.7248 (2)	0.37519 (16)	0.24941 (9)	0.0651 (4)
C13	0.5158 (2)	0.29696 (19)	0.12951 (11)	0.0442 (4)
H13	0.509 (3)	0.215 (2)	0.1320 (13)	0.053*
O13	0.5895 (2)	0.32710 (14)	0.07193 (8)	0.0549 (4)
C13A	0.5943 (5)	0.2339 (3)	0.01705 (16)	0.0825 (8)
H13B	0.6475	0.2612	−0.0210	0.124*
H13C	0.4802	0.2027	−0.0054	0.124*
H13D	0.6582	0.1750	0.0405	0.124*
C14	0.3417 (2)	0.34628 (17)	0.14070 (11)	0.0415 (4)
S11	0.16578 (6)	0.23419 (5)	0.12530 (3)	0.04935 (17)
O11A	0.0944 (2)	0.22094 (17)	0.04683 (10)	0.0735 (5)
O11B	0.2375 (2)	0.13749 (15)	0.15927 (11)	0.0698 (5)
C11C	0.0143 (3)	0.2841 (2)	0.17402 (18)	0.0708 (7)
H11A	−0.0795	0.2268	0.1669	0.106*
H11B	−0.0262	0.3541	0.1553	0.106*
H11C	0.0655	0.2989	0.2265	0.106*
S12	0.28541 (6)	0.47460 (4)	0.09142 (3)	0.04868 (17)
O12A	0.1274 (2)	0.50808 (15)	0.10762 (10)	0.0643 (4)
O12B	0.4326 (2)	0.55445 (15)	0.11502 (10)	0.0644 (4)
C12C	0.2555 (3)	0.4339 (2)	−0.00546 (13)	0.0616 (6)
H12B	0.2260	0.4993	−0.0325	0.092*
H12C	0.1653	0.3737	−0.0205	0.092*
H12D	0.3588	0.4065	−0.0162	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0363 (8)	0.0448 (9)	0.0467 (9)	0.0018 (6)	0.0128 (7)	0.0056 (7)
C1'	0.0379 (10)	0.0489 (11)	0.0436 (10)	0.0041 (7)	0.0104 (8)	0.0048 (8)
C2'	0.0719 (15)	0.0487 (13)	0.0592 (13)	0.0057 (9)	0.0284 (11)	0.0124 (10)
C3'	0.0824 (17)	0.0496 (13)	0.0672 (14)	0.0136 (11)	0.0305 (13)	0.0092 (11)
C4'	0.0433 (11)	0.0647 (14)	0.0474 (11)	0.0101 (9)	0.0112 (9)	0.0011 (10)
O4'	0.0724 (11)	0.0779 (12)	0.0605 (10)	0.0228 (8)	0.0274 (8)	0.0026 (8)
C4'A	0.0678 (17)	0.095 (2)	0.0774 (17)	0.0034 (13)	0.0396 (14)	−0.0035 (15)
C5'	0.0558 (13)	0.0634 (14)	0.0486 (11)	0.0009 (9)	0.0209 (10)	0.0086 (10)
C6'	0.0549 (12)	0.0504 (12)	0.0503 (11)	0.0049 (8)	0.0165 (9)	0.0096 (9)
C2	0.0392 (11)	0.0444 (11)	0.0544 (11)	0.0004 (8)	0.0157 (9)	0.0104 (9)
O2	0.0462 (9)	0.0682 (10)	0.0729 (10)	−0.0119 (7)	0.0169 (8)	−0.0051 (8)
C3	0.0401 (10)	0.0480 (11)	0.0486 (11)	0.0015 (7)	0.0168 (9)	0.0094 (9)
O3	0.0515 (9)	0.0591 (9)	0.0650 (9)	0.0068 (6)	0.0262 (7)	0.0010 (7)
C3A	0.116 (3)	0.081 (2)	0.0787 (18)	−0.0078 (16)	0.0567 (18)	−0.0144 (16)
C4	0.0362 (10)	0.0431 (10)	0.0426 (9)	0.0030 (7)	0.0112 (8)	0.0096 (8)
S1	0.0404 (3)	0.0593 (3)	0.0526 (3)	0.0032 (2)	0.0051 (2)	0.0183 (2)
O1A	0.0573 (10)	0.0699 (11)	0.0903 (13)	0.0094 (7)	0.0130 (9)	0.0426 (10)
O1B	0.0735 (12)	0.0870 (13)	0.0602 (10)	−0.0012 (9)	−0.0082 (9)	0.0026 (9)
C1C	0.0398 (12)	0.097 (2)	0.0862 (18)	0.0175 (11)	0.0143 (12)	0.0300 (15)
S2	0.0489 (3)	0.0430 (3)	0.0536 (3)	0.00230 (19)	0.0169 (2)	0.0126 (2)
O2A	0.0645 (11)	0.0621 (10)	0.0856 (12)	0.0004 (7)	0.0393 (9)	0.0214 (9)
O2B	0.0664 (10)	0.0581 (10)	0.0667 (10)	0.0130 (7)	0.0040 (8)	0.0226 (8)
C2C	0.0720 (16)	0.0483 (13)	0.0774 (16)	−0.0060 (10)	0.0228 (13)	−0.0009 (12)
N11	0.0370 (9)	0.0534 (10)	0.0432 (8)	0.0072 (6)	0.0090 (7)	0.0125 (7)
C11'	0.0414 (10)	0.0473 (11)	0.0446 (10)	0.0062 (7)	0.0115 (8)	0.0110 (8)
C12'	0.0690 (15)	0.0580 (14)	0.0572 (13)	0.0270 (10)	0.0224 (11)	0.0199 (11)
C13'	0.0803 (17)	0.0681 (16)	0.0561 (13)	0.0268 (12)	0.0254 (12)	0.0293 (12)
C14'	0.0638 (14)	0.0607 (14)	0.0512 (12)	0.0147 (10)	0.0227 (10)	0.0160 (10)
O14'	0.1083 (16)	0.0852 (13)	0.0670 (11)	0.0388 (11)	0.0498 (11)	0.0284 (10)
C14A	0.126 (3)	0.103 (2)	0.0623 (16)	0.034 (2)	0.0462 (18)	0.0326 (16)
C15'	0.0788 (16)	0.0561 (14)	0.0610 (13)	0.0271 (11)	0.0274 (12)	0.0169 (11)
C16'	0.0700 (15)	0.0523 (13)	0.0528 (12)	0.0204 (10)	0.0195 (11)	0.0200 (10)
C12	0.0382 (11)	0.0531 (12)	0.0492 (11)	0.0063 (8)	0.0099 (9)	0.0160 (9)
O12	0.0395 (8)	0.0927 (13)	0.0604 (9)	0.0076 (7)	0.0028 (7)	0.0098 (9)
C13	0.0398 (10)	0.0478 (11)	0.0488 (11)	0.0064 (7)	0.0137 (8)	0.0134 (9)
O13	0.0541 (9)	0.0642 (10)	0.0533 (8)	0.0045 (6)	0.0241 (7)	0.0130 (7)
C13A	0.108 (2)	0.089 (2)	0.0574 (14)	0.0149 (16)	0.0341 (15)	0.0035 (14)
C14	0.0375 (10)	0.0453 (11)	0.0438 (10)	0.0025 (7)	0.0103 (8)	0.0122 (8)
S11	0.0417 (3)	0.0513 (3)	0.0565 (3)	−0.00347 (19)	0.0116 (2)	0.0153 (2)
O11A	0.0682 (11)	0.0852 (13)	0.0586 (10)	−0.0230 (9)	0.0013 (8)	0.0087 (9)
O11B	0.0616 (10)	0.0560 (10)	0.0975 (13)	0.0021 (7)	0.0205 (9)	0.0332 (9)
C11C	0.0473 (13)	0.0762 (17)	0.0951 (19)	−0.0040 (11)	0.0293 (13)	0.0153 (14)
S12	0.0445 (3)	0.0504 (3)	0.0528 (3)	0.00508 (19)	0.0076 (2)	0.0212 (2)
O12A	0.0565 (9)	0.0701 (11)	0.0737 (11)	0.0244 (7)	0.0169 (8)	0.0279 (9)
O12B	0.0637 (10)	0.0542 (9)	0.0727 (10)	−0.0078 (7)	0.0060 (8)	0.0216 (8)
C12C	0.0597 (14)	0.0758 (16)	0.0500 (12)	0.0021 (11)	0.0057 (10)	0.0272 (11)

Geometric parameters (Å, º)

N1—C2	1.376 (3)	N11—C12	1.378 (3)
N1—C1'	1.430 (3)	N11—C11'	1.432 (3)
N1—C4	1.449 (2)	N11—C14	1.448 (3)
C1'—C6'	1.377 (3)	C11'—C12'	1.372 (3)
C1'—C2'	1.383 (3)	C11'—C16'	1.384 (3)
C2'—C3'	1.373 (3)	C12'—C13'	1.383 (3)
C2'—H2'A	0.9300	C12'—H12A	0.9300
C3'—C4'	1.390 (3)	C13'—C14'	1.376 (3)
C3'—H3'A	0.9300	C13'—H13A	0.9300
C4'—O4'	1.359 (3)	C14'—O14'	1.355 (3)
C4'—C5'	1.378 (3)	C14'—C15'	1.383 (3)
O4'—C4'A	1.422 (3)	O14'—C14A	1.418 (3)
C4'A—H4'A	0.9600	C14A—H14A	0.9600
C4'A—H4'B	0.9600	C14A—H14B	0.9600
C4'A—H4'C	0.9600	C14A—H14C	0.9600
C5'—C6'	1.387 (3)	C15'—C16'	1.376 (3)
C5'—H5'A	0.9300	C15'—H15A	0.9300
C6'—H6'A	0.9300	C16'—H16A	0.9300
C2—O2	1.199 (3)	C12—O12	1.197 (3)
C2—C3	1.529 (3)	C12—C13	1.529 (3)
C3—O3	1.372 (2)	C13—O13	1.377 (2)
C3—C4	1.591 (3)	C13—C14	1.591 (3)
C3—H3	0.98 (3)	C13—H13	0.96 (2)
O3—C3A	1.431 (3)	O13—C13A	1.422 (3)
C3A—H3AA	0.9600	C13A—H13B	0.9600
C3A—H3AB	0.9600	C13A—H13C	0.9600
C3A—H3AC	0.9600	C13A—H13D	0.9600
C4—S1	1.8232 (19)	C14—S11	1.8317 (19)
C4—S2	1.8468 (19)	C14—S12	1.845 (2)
S1—O1B	1.4222 (19)	S11—O11A	1.4228 (18)
S1—O1A	1.4329 (18)	S11—O11B	1.4285 (18)
S1—C1C	1.754 (3)	S11—C11C	1.753 (3)
C1C—H1CA	0.9600	C11C—H11A	0.9600
C1C—H1CB	0.9600	C11C—H11B	0.9600
C1C—H1CC	0.9600	C11C—H11C	0.9600
S2—O2B	1.4280 (18)	S12—O12B	1.4316 (17)
S2—O2A	1.4287 (17)	S12—O12A	1.4340 (17)
S2—C2C	1.752 (2)	S12—C12C	1.759 (2)
C2C—H2CA	0.9600	C12C—H12B	0.9600
C2C—H2CB	0.9600	C12C—H12C	0.9600
C2C—H2CC	0.9600	C12C—H12D	0.9600
C2—N1—C1'	131.98 (17)	C12—N11—C11'	130.44 (17)
C2—N1—C4	95.63 (15)	C12—N11—C14	95.47 (15)
C1'—N1—C4	131.89 (15)	C11'—N11—C14	133.13 (16)
C6'—C1'—C2'	119.90 (19)	C12'—C11'—C16'	119.76 (19)
C6'—C1'—N1	121.08 (18)	C12'—C11'—N11	118.45 (18)
C2'—C1'—N1	119.01 (18)	C16'—C11'—N11	121.77 (18)
C3'—C2'—C1'	120.0 (2)	C11'—C12'—C13'	120.7 (2)
C3'—C2'—H2'A	120.0	C11'—C12'—H12A	119.6
C1'—C2'—H2'A	120.0	C13'—C12'—H12A	119.6
C2'—C3'—C4'	120.3 (2)	C14'—C13'—C12'	119.6 (2)
C2'—C3'—H3'A	119.8	C14'—C13'—H13A	120.2
C4'—C3'—H3'A	119.8	C12'—C13'—H13A	120.2
O4'—C4'—C5'	125.2 (2)	O14'—C14'—C13'	124.8 (2)
O4'—C4'—C3'	115.1 (2)	O14'—C14'—C15'	115.7 (2)
C5'—C4'—C3'	119.6 (2)	C13'—C14'—C15'	119.5 (2)
C4'—O4'—C4'A	118.0 (2)	C14'—O14'—C14A	118.7 (2)
O4'—C4'A—H4'A	109.5	O14'—C14A—H14A	109.5
O4'—C4'A—H4'B	109.5	O14'—C14A—H14B	109.5
H4'A—C4'A—H4'B	109.5	H14A—C14A—H14B	109.5
O4'—C4'A—H4'C	109.5	O14'—C14A—H14C	109.5
H4'A—C4'A—H4'C	109.5	H14A—C14A—H14C	109.5
H4'B—C4'A—H4'C	109.5	H14B—C14A—H14C	109.5
C4'—C5'—C6'	119.9 (2)	C16'—C15'—C14'	120.8 (2)
C4'—C5'—H5'A	120.1	C16'—C15'—H15A	119.6
C6'—C5'—H5'A	120.1	C14'—C15'—H15A	119.6
C1'—C6'—C5'	120.2 (2)	C15'—C16'—C11'	119.4 (2)
C1'—C6'—H6'A	119.9	C15'—C16'—H16A	120.3
C5'—C6'—H6'A	119.9	C11'—C16'—H16A	120.3
O2—C2—N1	131.5 (2)	O12—C12—N11	132.0 (2)
O2—C2—C3	136.33 (19)	O12—C12—C13	136.0 (2)
N1—C2—C3	92.17 (15)	N11—C12—C13	91.95 (15)
O3—C3—C2	117.97 (18)	O13—C13—C12	118.83 (17)
O3—C3—C4	120.39 (17)	O13—C13—C14	121.00 (17)
C2—C3—C4	84.26 (14)	C12—C13—C14	84.20 (14)
O3—C3—H3	111.4 (14)	O13—C13—H13	112.0 (14)
C2—C3—H3	111.7 (14)	C12—C13—H13	108.4 (14)
C4—C3—H3	108.3 (14)	C14—C13—H13	109.2 (14)
C3—O3—C3A	114.3 (2)	C13—O13—C13A	114.17 (19)
O3—C3A—H3AA	109.5	O13—C13A—H13B	109.5
O3—C3A—H3AB	109.5	O13—C13A—H13C	109.5
H3AA—C3A—H3AB	109.5	H13B—C13A—H13C	109.5
O3—C3A—H3AC	109.5	O13—C13A—H13D	109.5
H3AA—C3A—H3AC	109.5	H13B—C13A—H13D	109.5
H3AB—C3A—H3AC	109.5	H13C—C13A—H13D	109.5
N1—C4—C3	87.02 (14)	N11—C14—C13	86.91 (14)
N1—C4—S1	114.94 (13)	N11—C14—S11	115.94 (13)
C3—C4—S1	112.10 (13)	C13—C14—S11	112.92 (13)
N1—C4—S2	111.00 (13)	N11—C14—S12	110.72 (13)
C3—C4—S2	115.31 (13)	C13—C14—S12	114.47 (13)
S1—C4—S2	113.81 (10)	S11—C14—S12	113.34 (10)
O1B—S1—O1A	118.38 (12)	O11A—S11—O11B	118.47 (13)
O1B—S1—C1C	110.46 (14)	O11A—S11—C11C	109.66 (14)
O1A—S1—C1C	107.77 (13)	O11B—S11—C11C	108.51 (13)
O1B—S1—C4	105.88 (11)	O11A—S11—C14	106.35 (9)
O1A—S1—C4	105.52 (10)	O11B—S11—C14	105.47 (10)
C1C—S1—C4	108.35 (11)	C11C—S11—C14	107.83 (11)
S1—C1C—H1CA	109.5	S11—C11C—H11A	109.5
S1—C1C—H1CB	109.5	S11—C11C—H11B	109.5
H1CA—C1C—H1CB	109.5	H11A—C11C—H11B	109.5
S1—C1C—H1CC	109.5	S11—C11C—H11C	109.5
H1CA—C1C—H1CC	109.5	H11A—C11C—H11C	109.5
H1CB—C1C—H1CC	109.5	H11B—C11C—H11C	109.5
O2B—S2—O2A	118.74 (11)	O12B—S12—O12A	118.33 (12)
O2B—S2—C2C	109.64 (12)	O12B—S12—C12C	109.04 (12)
O2A—S2—C2C	108.47 (12)	O12A—S12—C12C	109.03 (11)
O2B—S2—C4	104.24 (10)	O12B—S12—C14	104.80 (9)
O2A—S2—C4	106.85 (9)	O12A—S12—C14	107.34 (9)
C2C—S2—C4	108.42 (11)	C12C—S12—C14	107.79 (11)
S2—C2C—H2CA	109.5	S12—C12C—H12B	109.5
S2—C2C—H2CB	109.5	S12—C12C—H12C	109.5
H2CA—C2C—H2CB	109.5	H12B—C12C—H12C	109.5
S2—C2C—H2CC	109.5	S12—C12C—H12D	109.5
H2CA—C2C—H2CC	109.5	H12B—C12C—H12D	109.5
H2CB—C2C—H2CC	109.5	H12C—C12C—H12D	109.5
N1—C2—C3—C4	−7.08 (15)	N1—C4—S2—C2C	−156.18 (14)
C2—N1—C1'—C2'	59.6 (3)	C3—C4—S2—C2C	−59.29 (17)
C2—C3—O3—C3A	−145.6 (2)	S1—C4—S2—C2C	72.28 (14)
N11—C12—C13—C14	8.93 (14)	C12—N11—C11'—C12'	−55.4 (3)
C14—N11—C11'—C12'	110.5 (3)	C12—N11—C11'—C16'	125.9 (2)
C12—C13—O13—C13A	144.5 (2)	C14—N11—C11'—C16'	−68.2 (3)
C2—N1—C1'—C6'	−121.0 (2)	C16'—C11'—C12'—C13'	−0.5 (4)
C4—N1—C1'—C6'	69.2 (3)	N11—C11'—C12'—C13'	−179.2 (2)
C4—N1—C1'—C2'	−110.2 (2)	C11'—C12'—C13'—C14'	1.1 (4)
C6'—C1'—C2'—C3'	−1.8 (4)	C12'—C13'—C14'—O14'	179.1 (3)
N1—C1'—C2'—C3'	177.5 (2)	C12'—C13'—C14'—C15'	−0.2 (4)
C1'—C2'—C3'—C4'	−0.9 (4)	C13'—C14'—O14'—C14A	6.2 (5)
C2'—C3'—C4'—O4'	−176.7 (2)	C15'—C14'—O14'—C14A	−174.5 (3)
C2'—C3'—C4'—C5'	2.6 (4)	O14'—C14'—C15'—C16'	179.3 (3)
C5'—C4'—O4'—C4'A	1.5 (4)	C13'—C14'—C15'—C16'	−1.3 (4)
C3'—C4'—O4'—C4'A	−179.3 (2)	C14'—C15'—C16'—C11'	1.9 (4)
O4'—C4'—C5'—C6'	177.7 (2)	C12'—C11'—C16'—C15'	−1.1 (4)
C3'—C4'—C5'—C6'	−1.5 (4)	N11—C11'—C16'—C15'	177.7 (2)
C2'—C1'—C6'—C5'	2.9 (3)	C11'—N11—C12—O12	−18.7 (4)
N1—C1'—C6'—C5'	−176.46 (19)	C14—N11—C12—O12	171.5 (2)
C4'—C5'—C6'—C1'	−1.2 (3)	C11'—N11—C12—C13	159.9 (2)
C1'—N1—C2—O2	14.3 (4)	C14—N11—C12—C13	−9.81 (16)
C4—N1—C2—O2	−173.3 (2)	O12—C12—C13—O13	−50.2 (4)
C1'—N1—C2—C3	−164.6 (2)	N11—C12—C13—O13	131.28 (19)
C4—N1—C2—C3	7.78 (16)	O12—C12—C13—C14	−172.5 (3)
O2—C2—C3—O3	52.6 (4)	C14—C13—O13—C13A	−114.1 (2)
N1—C2—C3—O3	−128.57 (18)	C12—N11—C14—C13	9.43 (15)
O2—C2—C3—C4	174.1 (3)	C11'—N11—C14—C13	−159.8 (2)
C4—C3—O3—C3A	114.0 (2)	C12—N11—C14—S11	123.48 (15)
C2—N1—C4—C3	−7.48 (16)	C11'—N11—C14—S11	−45.8 (3)
C1'—N1—C4—C3	164.9 (2)	C12—N11—C14—S12	−105.60 (14)
C2—N1—C4—S1	−120.51 (14)	C11'—N11—C14—S12	85.1 (2)
C1'—N1—C4—S1	51.9 (2)	O13—C13—C14—N11	−128.79 (19)
C2—N1—C4—S2	108.53 (14)	C12—C13—C14—N11	−8.50 (14)
C1'—N1—C4—S2	−79.1 (2)	O13—C13—C14—S11	114.28 (19)
O3—C3—C4—N1	125.91 (19)	C12—C13—C14—S11	−125.42 (14)
C2—C3—C4—N1	6.73 (14)	O13—C13—C14—S12	−17.4 (2)
O3—C3—C4—S1	−118.33 (18)	C12—C13—C14—S12	102.89 (15)
C2—C3—C4—S1	122.49 (14)	N11—C14—S11—O11A	176.02 (15)
O3—C3—C4—S2	14.0 (2)	C13—C14—S11—O11A	−85.89 (16)
C2—C3—C4—S2	−105.13 (15)	S12—C14—S11—O11A	46.36 (15)
N1—C4—S1—O1B	178.33 (14)	N11—C14—S11—O11B	−57.34 (17)
C3—C4—S1—O1B	81.04 (16)	C13—C14—S11—O11B	40.75 (17)
S2—C4—S1—O1B	−52.09 (14)	S12—C14—S11—O11B	172.99 (11)
N1—C4—S1—O1A	52.04 (16)	N11—C14—S11—C11C	58.46 (18)
C3—C4—S1—O1A	−45.25 (17)	C13—C14—S11—C11C	156.54 (16)
S2—C4—S1—O1A	−178.37 (11)	S12—C14—S11—C11C	−71.21 (15)
N1—C4—S1—C1C	−63.17 (18)	N11—C14—S12—O12B	43.27 (16)
C3—C4—S1—C1C	−160.45 (16)	C13—C14—S12—O12B	−52.98 (17)
S2—C4—S1—C1C	66.42 (15)	S11—C14—S12—O12B	175.53 (11)
N1—C4—S2—O2B	−39.43 (15)	N11—C14—S12—O12A	−83.37 (15)
C3—C4—S2—O2B	57.46 (16)	C13—C14—S12—O12A	−179.62 (14)
S1—C4—S2—O2B	−170.97 (11)	S11—C14—S12—O12A	48.89 (14)
N1—C4—S2—O2A	87.10 (15)	N11—C14—S12—C12C	159.31 (14)
C3—C4—S2—O2A	−176.01 (14)	C13—C14—S12—C12C	63.06 (17)
S1—C4—S2—O2A	−44.44 (14)	S11—C14—S12—C12C	−68.43 (13)