Benzhydryl 2-(3-benzyl-7-oxo-4-thia-2,6-diaza­bicyclo­[3.2.0]hept-2-en-6-yl)-3-hydroxy­but-2-enoate

There are two mol­ecules in the asymmetric unit of the title compound, C₂₈H₂₄N₂O₄S, an important inter­mediate in the synthesis of the cephem nucleus, which is convertible into broad-spectrum cephalosporin anti­biotics. The two molecules have comparable conformations.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.039
• wR factor = 0.080
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



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           27.87
           From the CIF: _reflns_number_total              11441
           Count of symmetry unique reflns         6044
           Completeness (_total/calc)            189.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5397
           Fraction of Friedel pairs measured     0.893
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 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
   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

---

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Benzhydryl 2-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl)- 3-hydroxybut-2-enoate

Crystal data

C28H24N2O4S	F(000) = 1016
Mr = 484.55	Dx = 1.330 Mg m^−3
Monoclinic, P21	Melting point = 400–401 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.7107 Å
a = 14.1146 (12) Å	Cell parameters from 7417 reflections
b = 11.4794 (10) Å	θ = 1.6–27.9°
c = 16.0864 (16) Å	µ = 0.17 mm^−1
β = 111.765 (3)°	T = 113 K
V = 2420.6 (4) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn CCD diffractometer	11441 independent reflections
Radiation source: rotating anode	9572 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.043
ω scans	θmax = 27.9°, θmin = 1.4°
Absorption correction: multi-scan (Jacobson, 1998)	h = −18→18
Tmin = 0.963, Tmax = 0.973	k = −15→15
30634 measured reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0403P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max = 0.002
S = 0.98	Δρmax = 0.21 e Å^−3
11441 reflections	Δρmin = −0.22 e Å^−3
665 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
45 restraints	Extinction coefficient: 0.0131 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 5406 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (4)

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	Occ. (<1)
S1	0.37900 (3)	0.63716 (4)	0.77691 (3)	0.02255 (10)
S2	0.06078 (4)	0.14501 (4)	0.65852 (3)	0.03018 (12)
N1	0.25222 (11)	0.83185 (12)	0.74418 (9)	0.0193 (3)
N2	0.35561 (12)	0.73544 (12)	0.62193 (10)	0.0227 (3)
N3	0.19602 (11)	0.33308 (12)	0.70178 (9)	0.0191 (3)
N4	0.10100 (12)	0.21186 (14)	0.82487 (10)	0.0257 (3)
O1	0.23868 (10)	0.97155 (11)	0.63297 (8)	0.0282 (3)
O2	0.32586 (11)	0.99554 (12)	0.95280 (9)	0.0302 (3)
H2	0.2647 (18)	0.985 (2)	0.9521 (15)	0.045*
O3	0.13864 (9)	0.93036 (11)	0.89970 (8)	0.0257 (3)
O4	0.07800 (9)	0.82372 (10)	0.77290 (7)	0.0201 (3)
O5	0.22671 (10)	0.45291 (11)	0.82761 (9)	0.0293 (3)
O6	0.18750 (11)	0.50971 (11)	0.51010 (8)	0.0262 (3)
H6	0.2537 (17)	0.502 (2)	0.5221 (14)	0.039*
O7	0.37195 (9)	0.44220 (10)	0.60417 (8)	0.0217 (3)
O8	0.39147 (8)	0.32623 (10)	0.72341 (7)	0.0200 (3)
C1	0.24569 (13)	0.87414 (16)	0.66235 (12)	0.0214 (4)
C2	0.25719 (14)	0.75108 (14)	0.62898 (12)	0.0214 (4)
H2A	0.1977	0.7238	0.5759	0.026*
C3	0.25830 (13)	0.70753 (15)	0.72179 (11)	0.0198 (4)
H3	0.1977	0.6598	0.7184	0.024*
C4	0.42019 (14)	0.68601 (15)	0.69080 (12)	0.0220 (4)
C5	0.53022 (14)	0.66788 (16)	0.70380 (13)	0.0299 (4)
H5A	0.5408	0.6935	0.6511	0.036*	0.528 (19)
H5B	0.5458	0.5862	0.7114	0.036*	0.528 (19)
H5C	0.5412	0.6915	0.6508	0.036*	0.472 (19)
H5D	0.5473	0.5868	0.7142	0.036*	0.472 (19)
C6	0.60031 (11)	0.7326 (2)	0.78239 (11)	0.0201 (18)	0.528 (19)
C7	0.61615 (13)	0.85189 (18)	0.7802 (3)	0.0220 (14)	0.528 (19)
H7A	0.5886	0.8931	0.7252	0.026*	0.528 (19)
C8	0.67237 (18)	0.9109 (5)	0.8584 (4)	0.0255 (13)	0.528 (19)
H8A	0.6832	0.9924	0.8569	0.031*	0.528 (19)
C9	0.71274 (17)	0.8506 (9)	0.9389 (3)	0.0360 (16)	0.528 (19)
H9A	0.7512	0.8909	0.9924	0.043*	0.528 (19)
C10	0.69690 (16)	0.7313 (9)	0.94111 (12)	0.0454 (17)	0.528 (19)
H10A	0.7245	0.6901	0.9961	0.054*	0.528 (19)
C11	0.64068 (14)	0.6723 (5)	0.8629 (3)	0.0359 (13)	0.528 (19)
H11A	0.6299	0.5908	0.8644	0.043*	0.528 (19)
C6'	0.59937 (11)	0.7418 (2)	0.78532 (10)	0.027 (2)	0.472 (19)
C7'	0.61271 (14)	0.85743 (15)	0.7666 (3)	0.0320 (18)	0.472 (19)
H7'A	0.5855	0.8848	0.7066	0.038*	0.472 (19)
C8'	0.66590 (19)	0.9331 (4)	0.8356 (5)	0.0389 (15)	0.472 (19)
H8'A	0.6750	1.0122	0.8227	0.047*	0.472 (19)
C9'	0.70574 (19)	0.8931 (8)	0.9233 (4)	0.0412 (16)	0.472 (19)
H9'A	0.7421	0.9448	0.9705	0.049*	0.472 (19)
C10'	0.69240 (16)	0.7774 (9)	0.94211 (9)	0.0446 (17)	0.472 (19)
H10B	0.7196	0.7500	1.0021	0.054*	0.472 (19)
C11'	0.63922 (13)	0.7017 (6)	0.87310 (18)	0.0345 (14)	0.472 (19)
H11B	0.6301	0.6227	0.8859	0.041*	0.472 (19)
C12	0.24690 (13)	0.88710 (14)	0.82101 (11)	0.0195 (4)
C13	0.33032 (14)	0.94057 (15)	0.88115 (12)	0.0237 (4)
C14	0.43228 (14)	0.94572 (17)	0.87448 (14)	0.0303 (4)
H14A	0.4442	1.0244	0.8569	0.045*
H14B	0.4351	0.8897	0.8295	0.045*
H14C	0.4849	0.9265	0.9327	0.045*
C15	0.15156 (13)	0.88373 (14)	0.83595 (11)	0.0191 (4)
C16	−0.01877 (13)	0.81094 (16)	0.78606 (11)	0.0219 (4)
H16	−0.0357	0.8864	0.8084	0.026*
C17	−0.09879 (14)	0.78478 (16)	0.69590 (12)	0.0232 (4)
C18	−0.07854 (14)	0.71605 (18)	0.63312 (12)	0.0273 (4)
H18	−0.0115	0.6874	0.6456	0.033*
C19	−0.15646 (16)	0.68921 (17)	0.55203 (12)	0.0317 (5)
H19	−0.1424	0.6425	0.5092	0.038*
C20	−0.25349 (16)	0.73013 (18)	0.53400 (13)	0.0353 (5)
H20	−0.3065	0.7104	0.4790	0.042*
C21	−0.27465 (15)	0.79966 (18)	0.59503 (14)	0.0370 (5)
H21	−0.3416	0.8290	0.5818	0.044*
C22	−0.19698 (14)	0.82628 (17)	0.67603 (14)	0.0305 (4)
H22	−0.2114	0.8736	0.7184	0.037*
C23	−0.00943 (13)	0.71639 (16)	0.85469 (11)	0.0215 (4)
C24	0.04382 (13)	0.61344 (15)	0.85678 (11)	0.0230 (4)
H24	0.0776	0.6027	0.8161	0.028*
C25	0.04781 (14)	0.52683 (16)	0.91774 (13)	0.0284 (4)
H25	0.0838	0.4567	0.9183	0.034*
C26	−0.00030 (16)	0.54167 (18)	0.97777 (13)	0.0332 (5)
H26	0.0028	0.4820	1.0196	0.040*
C27	−0.05300 (16)	0.6438 (2)	0.97669 (12)	0.0365 (5)
H27	−0.0856	0.6545	1.0182	0.044*
C28	−0.05819 (15)	0.73048 (17)	0.91498 (12)	0.0299 (4)
H28	−0.0953	0.7999	0.9139	0.036*
C29	0.21018 (13)	0.36151 (15)	0.78884 (12)	0.0206 (4)
C30	0.19513 (14)	0.23346 (16)	0.81120 (12)	0.0237 (4)
H30	0.2566	0.1981	0.8580	0.028*
C31	0.18576 (14)	0.20668 (15)	0.71319 (12)	0.0242 (4)
H31	0.2426	0.1586	0.7085	0.029*
C32	0.03120 (14)	0.17409 (14)	0.75479 (12)	0.0243 (4)
C33	−0.07784 (14)	0.15566 (16)	0.74769 (13)	0.0286 (4)
H33A	−0.1105	0.0944	0.7029	0.034*
H33B	−0.0786	0.1299	0.8062	0.034*
C34	−0.13629 (14)	0.26873 (16)	0.71998 (12)	0.0248 (4)
C35	−0.17898 (15)	0.30068 (18)	0.63035 (13)	0.0320 (5)
H35	−0.1749	0.2491	0.5856	0.038*
C36	−0.22760 (15)	0.4074 (2)	0.60560 (15)	0.0393 (5)
H36	−0.2563	0.4289	0.5442	0.047*
C37	−0.23420 (16)	0.48237 (19)	0.67042 (15)	0.0380 (5)
H37	−0.2677	0.5553	0.6536	0.046*
C38	−0.19206 (16)	0.45118 (17)	0.75980 (15)	0.0355 (5)
H38	−0.1970	0.5026	0.8043	0.043*
C39	−0.14261 (15)	0.34517 (16)	0.78470 (13)	0.0293 (4)
H39	−0.1129	0.3247	0.8462	0.035*
C40	0.22776 (14)	0.39442 (14)	0.63959 (11)	0.0194 (4)
C41	0.15855 (14)	0.45104 (15)	0.56867 (12)	0.0233 (4)
C42	0.04723 (15)	0.45508 (18)	0.54785 (13)	0.0335 (5)
H42A	0.0251	0.5364	0.5447	0.050*
H42B	0.0317	0.4145	0.5949	0.050*
H42C	0.0113	0.4170	0.4902	0.050*
C43	0.33537 (14)	0.39153 (14)	0.65294 (11)	0.0193 (4)
C44	0.49815 (13)	0.30847 (15)	0.73588 (11)	0.0197 (4)
H44	0.5274	0.3839	0.7255	0.024*
C45	0.55445 (13)	0.27081 (15)	0.83235 (11)	0.0207 (4)
C46	0.65878 (14)	0.25273 (17)	0.86066 (12)	0.0284 (4)
H46	0.6929	0.2682	0.8208	0.034*
C47	0.71417 (15)	0.21245 (19)	0.94624 (13)	0.0335 (5)
H47	0.7858	0.2014	0.9650	0.040*
C48	0.66478 (15)	0.18842 (16)	1.00432 (12)	0.0305 (4)
H48	0.7019	0.1580	1.0622	0.037*
C49	0.56179 (15)	0.20879 (18)	0.97777 (12)	0.0307 (4)
H49	0.5281	0.1940	1.0180	0.037*
C50	0.50621 (15)	0.25110 (17)	0.89199 (12)	0.0277 (4)
H50	0.4353	0.2664	0.8746	0.033*
C51	0.50514 (13)	0.21925 (16)	0.66863 (11)	0.0199 (4)
C52	0.45594 (14)	0.11231 (15)	0.65992 (11)	0.0222 (4)
H52	0.4194	0.0943	0.6974	0.027*
C53	0.45992 (14)	0.03193 (16)	0.59695 (12)	0.0262 (4)
H53	0.4252	−0.0404	0.5905	0.031*
C54	0.51500 (16)	0.05761 (18)	0.54326 (13)	0.0321 (5)
H54	0.5180	0.0028	0.5001	0.039*
C55	0.56531 (16)	0.16286 (19)	0.55277 (13)	0.0348 (5)
H55	0.6039	0.1801	0.5168	0.042*
C56	0.55934 (15)	0.24367 (17)	0.61514 (12)	0.0291 (4)
H56	0.5931	0.3165	0.6208	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0260 (2)	0.0213 (2)	0.0225 (2)	0.0001 (2)	0.01142 (19)	−0.00193 (19)
S2	0.0335 (3)	0.0278 (2)	0.0355 (3)	−0.0088 (2)	0.0201 (2)	−0.0111 (2)
N1	0.0252 (8)	0.0151 (7)	0.0205 (7)	−0.0022 (6)	0.0119 (6)	−0.0029 (6)
N2	0.0271 (9)	0.0204 (8)	0.0253 (8)	−0.0026 (6)	0.0150 (7)	−0.0058 (6)
N3	0.0234 (8)	0.0167 (7)	0.0194 (7)	−0.0006 (6)	0.0106 (6)	−0.0025 (6)
N4	0.0284 (9)	0.0248 (8)	0.0261 (8)	0.0003 (7)	0.0126 (7)	0.0064 (7)
O1	0.0396 (8)	0.0215 (7)	0.0297 (7)	0.0038 (6)	0.0198 (6)	0.0031 (5)
O2	0.0330 (8)	0.0315 (7)	0.0267 (7)	−0.0071 (6)	0.0119 (7)	−0.0105 (6)
O3	0.0293 (7)	0.0297 (7)	0.0220 (7)	−0.0005 (6)	0.0141 (6)	−0.0068 (5)
O4	0.0171 (6)	0.0248 (7)	0.0202 (6)	−0.0031 (5)	0.0090 (5)	−0.0031 (5)
O5	0.0348 (8)	0.0307 (8)	0.0270 (7)	−0.0067 (6)	0.0168 (6)	−0.0091 (6)
O6	0.0304 (8)	0.0264 (7)	0.0220 (7)	0.0055 (6)	0.0098 (6)	0.0054 (5)
O7	0.0263 (7)	0.0216 (6)	0.0195 (6)	−0.0027 (5)	0.0110 (6)	0.0003 (5)
O8	0.0193 (6)	0.0221 (6)	0.0189 (6)	0.0027 (5)	0.0076 (5)	0.0033 (5)
C1	0.0191 (10)	0.0232 (9)	0.0235 (9)	−0.0016 (7)	0.0097 (8)	−0.0025 (7)
C2	0.0239 (10)	0.0213 (9)	0.0207 (9)	−0.0050 (7)	0.0104 (8)	−0.0033 (7)
C3	0.0217 (9)	0.0165 (8)	0.0237 (9)	−0.0028 (7)	0.0115 (8)	−0.0043 (7)
C4	0.0261 (10)	0.0188 (9)	0.0255 (9)	−0.0055 (7)	0.0147 (8)	−0.0095 (7)
C5	0.0260 (11)	0.0291 (11)	0.0393 (11)	−0.0015 (8)	0.0175 (9)	−0.0100 (8)
C6	0.019 (4)	0.014 (3)	0.029 (4)	−0.004 (2)	0.012 (3)	0.003 (3)
C7	0.021 (3)	0.023 (3)	0.020 (2)	0.002 (2)	0.007 (2)	0.0040 (19)
C8	0.021 (2)	0.025 (2)	0.032 (3)	−0.0066 (17)	0.0111 (19)	−0.008 (2)
C9	0.034 (3)	0.044 (4)	0.027 (2)	−0.015 (2)	0.008 (2)	0.000 (3)
C10	0.040 (3)	0.051 (4)	0.034 (3)	−0.010 (2)	0.001 (2)	0.011 (2)
C11	0.039 (3)	0.032 (2)	0.031 (2)	0.0009 (18)	0.006 (2)	0.0087 (19)
C6'	0.017 (4)	0.040 (4)	0.026 (4)	0.012 (3)	0.012 (3)	0.000 (3)
C7'	0.031 (4)	0.032 (4)	0.031 (3)	0.002 (3)	0.008 (3)	−0.003 (2)
C8'	0.029 (3)	0.037 (3)	0.050 (3)	0.001 (2)	0.014 (2)	−0.002 (3)
C9'	0.022 (3)	0.048 (4)	0.041 (3)	0.006 (2)	−0.004 (3)	−0.015 (3)
C10'	0.038 (3)	0.064 (5)	0.023 (3)	0.016 (3)	0.000 (2)	0.018 (3)
C11'	0.039 (3)	0.027 (2)	0.040 (3)	0.005 (2)	0.016 (3)	0.014 (2)
C12	0.0250 (10)	0.0160 (8)	0.0201 (9)	−0.0001 (7)	0.0112 (8)	−0.0025 (7)
C13	0.0299 (11)	0.0198 (9)	0.0214 (9)	−0.0012 (7)	0.0095 (8)	−0.0013 (7)
C14	0.0247 (11)	0.0285 (11)	0.0356 (11)	−0.0080 (8)	0.0089 (9)	−0.0067 (9)
C15	0.0232 (10)	0.0174 (8)	0.0170 (8)	0.0007 (7)	0.0078 (8)	−0.0005 (7)
C16	0.0209 (10)	0.0245 (9)	0.0244 (9)	0.0005 (7)	0.0131 (8)	−0.0018 (7)
C17	0.0215 (10)	0.0235 (9)	0.0238 (9)	−0.0004 (7)	0.0076 (8)	0.0053 (7)
C18	0.0249 (10)	0.0325 (10)	0.0227 (9)	−0.0004 (8)	0.0068 (8)	0.0017 (8)
C19	0.0373 (12)	0.0337 (11)	0.0205 (9)	−0.0081 (9)	0.0064 (9)	0.0018 (8)
C20	0.0328 (12)	0.0338 (12)	0.0273 (10)	−0.0108 (9)	−0.0030 (9)	0.0125 (9)
C21	0.0220 (11)	0.0379 (12)	0.0438 (13)	−0.0015 (9)	0.0036 (10)	0.0176 (10)
C22	0.0252 (11)	0.0285 (10)	0.0382 (11)	0.0012 (8)	0.0123 (9)	0.0081 (9)
C23	0.0213 (10)	0.0241 (9)	0.0187 (8)	−0.0021 (7)	0.0068 (8)	−0.0025 (7)
C24	0.0198 (10)	0.0291 (11)	0.0200 (9)	0.0013 (7)	0.0071 (8)	0.0015 (7)
C25	0.0253 (11)	0.0269 (10)	0.0279 (10)	0.0013 (8)	0.0041 (9)	0.0032 (8)
C26	0.0395 (12)	0.0375 (12)	0.0212 (10)	−0.0034 (9)	0.0097 (9)	0.0082 (8)
C27	0.0490 (13)	0.0427 (12)	0.0268 (10)	−0.0048 (11)	0.0244 (10)	−0.0019 (10)
C28	0.0383 (12)	0.0284 (11)	0.0295 (10)	0.0002 (9)	0.0201 (9)	−0.0046 (8)
C29	0.0158 (9)	0.0267 (10)	0.0205 (9)	0.0015 (7)	0.0080 (7)	−0.0010 (7)
C30	0.0238 (10)	0.0251 (10)	0.0230 (9)	0.0036 (8)	0.0096 (8)	0.0042 (7)
C31	0.0249 (10)	0.0186 (9)	0.0327 (10)	0.0016 (8)	0.0150 (8)	−0.0015 (8)
C32	0.0283 (11)	0.0187 (9)	0.0303 (10)	0.0025 (7)	0.0161 (9)	0.0044 (7)
C33	0.0316 (11)	0.0249 (10)	0.0326 (10)	−0.0073 (8)	0.0159 (9)	0.0023 (8)
C34	0.0202 (10)	0.0278 (10)	0.0279 (10)	−0.0065 (8)	0.0108 (8)	0.0025 (8)
C35	0.0275 (11)	0.0413 (12)	0.0282 (10)	−0.0047 (9)	0.0115 (9)	0.0014 (9)
C36	0.0269 (12)	0.0531 (14)	0.0350 (12)	−0.0021 (10)	0.0079 (10)	0.0147 (10)
C37	0.0289 (12)	0.0303 (11)	0.0547 (14)	−0.0014 (9)	0.0153 (11)	0.0141 (10)
C38	0.0318 (12)	0.0314 (12)	0.0467 (13)	−0.0054 (9)	0.0185 (11)	−0.0058 (10)
C39	0.0284 (11)	0.0298 (11)	0.0304 (10)	−0.0055 (8)	0.0117 (9)	0.0015 (8)
C40	0.0238 (10)	0.0162 (8)	0.0197 (9)	0.0020 (7)	0.0099 (8)	−0.0010 (7)
C41	0.0284 (11)	0.0197 (9)	0.0218 (9)	0.0019 (7)	0.0093 (8)	−0.0030 (7)
C42	0.0307 (12)	0.0347 (12)	0.0321 (11)	0.0086 (9)	0.0084 (9)	0.0051 (9)
C43	0.0266 (10)	0.0152 (8)	0.0168 (8)	0.0014 (7)	0.0090 (8)	−0.0040 (7)
C44	0.0156 (9)	0.0217 (9)	0.0221 (9)	−0.0015 (7)	0.0075 (7)	0.0020 (7)
C45	0.0216 (10)	0.0188 (9)	0.0196 (9)	−0.0034 (7)	0.0054 (8)	−0.0034 (7)
C46	0.0225 (10)	0.0388 (12)	0.0239 (10)	−0.0020 (8)	0.0086 (8)	−0.0026 (8)
C47	0.0235 (11)	0.0410 (12)	0.0280 (10)	0.0034 (9)	0.0003 (9)	−0.0053 (9)
C48	0.0376 (12)	0.0273 (10)	0.0192 (9)	0.0010 (9)	0.0021 (9)	−0.0036 (8)
C49	0.0359 (12)	0.0344 (11)	0.0207 (9)	−0.0058 (9)	0.0092 (9)	−0.0025 (8)
C50	0.0244 (10)	0.0365 (11)	0.0192 (9)	−0.0030 (8)	0.0047 (8)	−0.0011 (8)
C51	0.0176 (9)	0.0243 (9)	0.0164 (8)	0.0061 (7)	0.0045 (7)	0.0047 (7)
C52	0.0233 (10)	0.0259 (10)	0.0171 (8)	0.0017 (7)	0.0073 (8)	0.0032 (7)
C53	0.0269 (11)	0.0237 (10)	0.0239 (10)	0.0036 (8)	0.0046 (8)	0.0005 (8)
C54	0.0347 (12)	0.0412 (12)	0.0193 (9)	0.0126 (9)	0.0087 (9)	−0.0015 (8)
C55	0.0350 (12)	0.0492 (14)	0.0277 (10)	0.0038 (10)	0.0204 (9)	0.0031 (9)
C56	0.0288 (11)	0.0345 (11)	0.0267 (10)	−0.0031 (8)	0.0135 (9)	0.0017 (8)

Geometric parameters (Å, º)

S1—C4	1.7800 (18)	C18—C19	1.394 (3)
S1—C3	1.7947 (18)	C18—H18	0.950
S2—C32	1.7786 (18)	C19—C20	1.373 (3)
S2—C31	1.7987 (19)	C19—H19	0.950
N1—C1	1.374 (2)	C20—C21	1.381 (3)
N1—C12	1.416 (2)	C20—H20	0.950
N1—C3	1.482 (2)	C21—C22	1.391 (3)
N2—C4	1.277 (2)	C21—H21	0.950
N2—C2	1.446 (2)	C22—H22	0.950
N3—C29	1.379 (2)	C23—C28	1.391 (2)
N3—C40	1.425 (2)	C23—C24	1.394 (2)
N3—C31	1.476 (2)	C24—C25	1.383 (2)
N4—C32	1.267 (2)	C24—H24	0.950
N4—C30	1.446 (2)	C25—C26	1.382 (3)
O1—C1	1.204 (2)	C25—H25	0.950
O2—C13	1.336 (2)	C26—C27	1.385 (3)
O2—H2	0.87 (2)	C26—H26	0.950
O3—C15	1.2288 (19)	C27—C28	1.388 (3)
O4—C15	1.342 (2)	C27—H27	0.950
O4—C16	1.465 (2)	C28—H28	0.950
O5—C29	1.198 (2)	C29—C30	1.547 (2)
O6—C41	1.339 (2)	C30—C31	1.563 (2)
O6—H6	0.89 (2)	C30—H30	1.000
O7—C43	1.2333 (19)	C31—H31	1.000
O8—C43	1.345 (2)	C32—C33	1.515 (3)
O8—C44	1.458 (2)	C33—C34	1.514 (3)
C1—C2	1.541 (2)	C33—H33A	0.990
C2—C3	1.569 (2)	C33—H33B	0.990
C2—H2A	1.000	C34—C39	1.389 (3)
C3—H3	1.000	C34—C35	1.390 (3)
C4—C5	1.503 (3)	C35—C36	1.389 (3)
C5—C6	1.484 (3)	C35—H35	0.950
C5—C6'	1.563 (2)	C36—C37	1.381 (3)
C5—H5A	0.960	C36—H36	0.950
C5—H5B	0.960	C37—C38	1.384 (3)
C5—H5C	0.960	C37—H37	0.950
C5—H5D	0.960	C38—C39	1.386 (3)
C6—C7	1.390	C38—H38	0.950
C6—C11	1.390	C39—H39	0.950
C7—C8	1.390	C40—C41	1.361 (2)
C7—H7A	0.950	C40—C43	1.453 (2)
C8—C9	1.390	C41—C42	1.481 (3)
C8—H8A	0.950	C42—H42A	0.980
C9—C10	1.390	C42—H42B	0.980
C9—H9A	0.950	C42—H42C	0.980
C10—C11	1.390	C44—C51	1.519 (2)
C10—H10A	0.950	C44—C45	1.520 (2)
C11—H11A	0.950	C44—H44	1.000
C6'—C7'	1.390	C45—C50	1.386 (2)
C6'—C11'	1.390	C45—C46	1.386 (3)
C7'—C8'	1.390	C46—C47	1.386 (3)
C7'—H7'A	0.950	C46—H46	0.950
C8'—C9'	1.390	C47—C48	1.385 (3)
C8'—H8'A	0.950	C47—H47	0.950
C9'—C10'	1.390	C48—C49	1.375 (3)
C9'—H9'A	0.950	C48—H48	0.950
C10'—C11'	1.390	C49—C50	1.397 (3)
C10'—H10B	0.950	C49—H49	0.950
C11'—H11B	0.950	C50—H50	0.950
C12—C13	1.362 (2)	C51—C56	1.376 (2)
C12—C15	1.453 (2)	C51—C52	1.392 (2)
C13—C14	1.483 (3)	C52—C53	1.387 (2)
C14—H14A	0.980	C52—H52	0.950
C14—H14B	0.980	C53—C54	1.391 (3)
C14—H14C	0.980	C53—H53	0.950
C16—C17	1.502 (2)	C54—C55	1.381 (3)
C16—C23	1.519 (2)	C54—H54	0.950
C16—H16	1.000	C55—C56	1.392 (3)
C17—C22	1.386 (3)	C55—H55	0.950
C17—C18	1.392 (2)	C56—H56	0.950
C4—S1—C3	89.87 (8)	C22—C21—H21	120.3
C32—S2—C31	90.27 (9)	C17—C22—C21	120.93 (19)
C1—N1—C12	132.21 (14)	C17—C22—H22	119.5
C1—N1—C3	95.55 (13)	C21—C22—H22	119.5
C12—N1—C3	132.08 (13)	C28—C23—C24	118.91 (17)
C4—N2—C2	112.60 (14)	C28—C23—C16	119.45 (16)
C29—N3—C40	129.16 (14)	C24—C23—C16	121.60 (15)
C29—N3—C31	95.18 (13)	C25—C24—C23	120.42 (17)
C40—N3—C31	130.10 (13)	C25—C24—H24	119.8
C32—N4—C30	112.24 (15)	C23—C24—H24	119.8
C13—O2—H2	106.6 (15)	C26—C25—C24	120.38 (18)
C15—O4—C16	116.34 (12)	C26—C25—H25	119.8
C41—O6—H6	111.7 (14)	C24—C25—H25	119.8
C43—O8—C44	116.70 (12)	C25—C26—C27	119.77 (18)
O1—C1—N1	132.15 (16)	C25—C26—H26	120.1
O1—C1—C2	135.96 (16)	C27—C26—H26	120.1
N1—C1—C2	91.81 (13)	C26—C27—C28	120.10 (17)
N2—C2—C1	111.68 (14)	C26—C27—H27	120.0
N2—C2—C3	111.35 (14)	C28—C27—H27	120.0
C1—C2—C3	85.75 (12)	C27—C28—C23	120.43 (18)
N2—C2—H2A	114.9	C27—C28—H28	119.8
C1—C2—H2A	114.9	C23—C28—H28	119.8
C3—C2—H2A	114.9	O5—C29—N3	131.52 (17)
N1—C3—C2	86.76 (12)	O5—C29—C30	136.73 (16)
N1—C3—S1	116.31 (12)	N3—C29—C30	91.75 (13)
C2—C3—S1	106.64 (11)	N4—C30—C29	114.30 (14)
N1—C3—H3	114.6	N4—C30—C31	112.38 (15)
C2—C3—H3	114.6	C29—C30—C31	85.40 (12)
S1—C3—H3	114.6	N4—C30—H30	113.9
N2—C4—C5	123.40 (16)	C29—C30—H30	113.9
N2—C4—S1	118.76 (13)	C31—C30—H30	113.9
C5—C4—S1	117.83 (14)	N3—C31—C30	87.52 (12)
C6—C5—C4	112.17 (15)	N3—C31—S2	116.72 (13)
C4—C5—C6'	109.47 (14)	C30—C31—S2	105.75 (12)
C6—C5—H5A	109.0	N3—C31—H31	114.5
C4—C5—H5A	109.0	C30—C31—H31	114.5
C6'—C5—H5A	108.7	S2—C31—H31	114.5
C6—C5—H5B	109.3	N4—C32—C33	123.21 (16)
C4—C5—H5B	109.2	N4—C32—S2	118.86 (14)
C6'—C5—H5B	112.3	C33—C32—S2	117.90 (14)
H5A—C5—H5B	108.0	C34—C33—C32	109.27 (14)
C6—C5—H5C	109.8	C34—C33—H33A	109.8
C4—C5—H5C	109.6	C32—C33—H33A	109.8
C6'—C5—H5C	109.6	C34—C33—H33B	109.8
H5B—C5—H5C	106.5	C32—C33—H33B	109.8
C6—C5—H5D	107.0	H33A—C33—H33B	108.3
C4—C5—H5D	109.8	C39—C34—C35	119.14 (18)
C6'—C5—H5D	110.0	C39—C34—C33	120.02 (17)
H5A—C5—H5D	109.8	C35—C34—C33	120.73 (17)
H5C—C5—H5D	108.3	C36—C35—C34	120.55 (19)
C7—C6—C11	120.0	C36—C35—H35	119.7
C7—C6—C5	122.30 (18)	C34—C35—H35	119.7
C11—C6—C5	117.23 (19)	C37—C36—C35	119.8 (2)
C6—C7—C8	120.0	C37—C36—H36	120.1
C6—C7—H7A	120.0	C35—C36—H36	120.1
C8—C7—H7A	120.0	C36—C37—C38	120.0 (2)
C9—C8—C7	120.0	C36—C37—H37	120.0
C9—C8—H8A	120.0	C38—C37—H37	120.0
C7—C8—H8A	120.0	C37—C38—C39	120.3 (2)
C8—C9—C10	120.0	C37—C38—H38	119.9
C8—C9—H9A	120.0	C39—C38—H38	119.9
C10—C9—H9A	120.0	C38—C39—C34	120.21 (19)
C9—C10—C11	120.0	C38—C39—H39	119.9
C9—C10—H10A	120.0	C34—C39—H39	119.9
C11—C10—H10A	120.0	C41—C40—N3	120.66 (15)
C10—C11—C6	120.0	C41—C40—C43	121.39 (16)
C10—C11—H11A	120.0	N3—C40—C43	117.93 (15)
C6—C11—H11A	120.0	O6—C41—C40	121.24 (16)
C7'—C6'—C11'	120.0	O6—C41—C42	113.58 (16)
C7'—C6'—C5	115.40 (18)	C40—C41—C42	125.19 (16)
C11'—C6'—C5	124.37 (18)	C41—C42—H42A	109.5
C8'—C7'—C6'	120.0	C41—C42—H42B	109.5
C8'—C7'—H7'A	120.0	H42A—C42—H42B	109.5
C6'—C7'—H7'A	120.0	C41—C42—H42C	109.5
C9'—C8'—C7'	120.0	H42A—C42—H42C	109.5
C9'—C8'—H8'A	120.0	H42B—C42—H42C	109.5
C7'—C8'—H8'A	120.0	O7—C43—O8	123.00 (15)
C8'—C9'—C10'	120.0	O7—C43—C40	123.81 (16)
C8'—C9'—H9'A	120.0	O8—C43—C40	113.19 (14)
C10'—C9'—H9'A	120.0	O8—C44—C51	109.44 (13)
C11'—C10'—C9'	120.0	O8—C44—C45	107.62 (13)
C11'—C10'—H10B	120.0	C51—C44—C45	112.81 (14)
C9'—C10'—H10B	120.0	O8—C44—H44	109.0
C10'—C11'—C6'	120.0	C51—C44—H44	109.0
C10'—C11'—H11B	120.0	C45—C44—H44	109.0
C6'—C11'—H11B	120.0	C50—C45—C46	118.88 (16)
C13—C12—N1	120.68 (16)	C50—C45—C44	123.23 (16)
C13—C12—C15	120.31 (15)	C46—C45—C44	117.87 (15)
N1—C12—C15	119.00 (15)	C45—C46—C47	121.02 (17)
O2—C13—C12	121.39 (17)	C45—C46—H46	119.5
O2—C13—C14	113.64 (16)	C47—C46—H46	119.5
C12—C13—C14	124.97 (16)	C48—C47—C46	119.79 (18)
C13—C14—H14A	109.5	C48—C47—H47	120.1
C13—C14—H14B	109.5	C46—C47—H47	120.1
H14A—C14—H14B	109.5	C49—C48—C47	119.69 (18)
C13—C14—H14C	109.5	C49—C48—H48	120.2
H14A—C14—H14C	109.5	C47—C48—H48	120.2
H14B—C14—H14C	109.5	C48—C49—C50	120.52 (17)
O3—C15—O4	122.81 (15)	C48—C49—H49	119.7
O3—C15—C12	124.03 (16)	C50—C49—H49	119.7
O4—C15—C12	113.16 (14)	C45—C50—C49	120.03 (18)
O4—C16—C17	106.74 (13)	C45—C50—H50	120.0
O4—C16—C23	110.02 (14)	C49—C50—H50	120.0
C17—C16—C23	113.00 (14)	C56—C51—C52	119.29 (16)
O4—C16—H16	109.0	C56—C51—C44	120.40 (16)
C17—C16—H16	109.0	C52—C51—C44	120.31 (15)
C23—C16—H16	109.0	C53—C52—C51	120.44 (17)
C22—C17—C18	118.96 (17)	C53—C52—H52	119.8
C22—C17—C16	118.93 (16)	C51—C52—H52	119.8
C18—C17—C16	122.06 (16)	C52—C53—C54	119.73 (18)
C17—C18—C19	120.08 (18)	C52—C53—H53	120.1
C17—C18—H18	120.0	C54—C53—H53	120.1
C19—C18—H18	120.0	C55—C54—C53	119.96 (18)
C20—C19—C18	120.09 (19)	C55—C54—H54	120.0
C20—C19—H19	120.0	C53—C54—H54	120.0
C18—C19—H19	120.0	C54—C55—C56	119.80 (18)
C19—C20—C21	120.60 (18)	C54—C55—H55	120.1
C19—C20—H20	119.7	C56—C55—H55	120.1
C21—C20—H20	119.7	C51—C56—C55	120.76 (18)
C20—C21—C22	119.34 (19)	C51—C56—H56	119.6
C20—C21—H21	120.3	C55—C56—H56	119.6
C12—N1—C1—O1	4.4 (3)	C28—C23—C24—C25	0.1 (3)
C3—N1—C1—O1	−179.9 (2)	C16—C23—C24—C25	−177.47 (16)
C12—N1—C1—C2	−178.66 (18)	C23—C24—C25—C26	−0.5 (3)
C3—N1—C1—C2	−2.98 (14)	C24—C25—C26—C27	0.2 (3)
C4—N2—C2—C1	96.47 (17)	C25—C26—C27—C28	0.6 (3)
C4—N2—C2—C3	2.47 (19)	C26—C27—C28—C23	−0.9 (3)
O1—C1—C2—N2	68.2 (3)	C24—C23—C28—C27	0.6 (3)
N1—C1—C2—N2	−108.49 (15)	C16—C23—C28—C27	178.24 (17)
O1—C1—C2—C3	179.5 (2)	C40—N3—C29—O5	22.3 (3)
N1—C1—C2—C3	2.81 (13)	C31—N3—C29—O5	177.5 (2)
C1—N1—C3—C2	2.93 (13)	C40—N3—C29—C30	−158.26 (16)
C12—N1—C3—C2	178.62 (18)	C31—N3—C29—C30	−3.05 (14)
C1—N1—C3—S1	109.90 (13)	C32—N4—C30—C29	96.20 (18)
C12—N1—C3—S1	−74.4 (2)	C32—N4—C30—C31	1.0 (2)
N2—C2—C3—N1	109.02 (14)	O5—C29—C30—N4	69.8 (3)
C1—C2—C3—N1	−2.61 (12)	N3—C29—C30—N4	−109.62 (16)
N2—C2—C3—S1	−7.49 (16)	O5—C29—C30—C31	−177.7 (2)
C1—C2—C3—S1	−119.12 (11)	N3—C29—C30—C31	2.88 (13)
C4—S1—C3—N1	−86.92 (13)	C29—N3—C31—C30	3.02 (14)
C4—S1—C3—C2	7.78 (12)	C40—N3—C31—C30	157.86 (17)
C2—N2—C4—C5	−175.07 (15)	C29—N3—C31—S2	109.42 (14)
C2—N2—C4—S1	4.18 (19)	C40—N3—C31—S2	−95.74 (19)
C3—S1—C4—N2	−7.67 (14)	N4—C30—C31—N3	111.73 (15)
C3—S1—C4—C5	171.63 (14)	C29—C30—C31—N3	−2.69 (12)
N2—C4—C5—C6	116.48 (19)	N4—C30—C31—S2	−5.36 (18)
S1—C4—C5—C6	−62.78 (19)	C29—C30—C31—S2	−119.78 (12)
N2—C4—C5—C6'	114.47 (18)	C32—S2—C31—N3	−89.19 (13)
S1—C4—C5—C6'	−64.79 (18)	C32—S2—C31—C30	6.07 (12)
C4—C5—C6—C7	−77.2 (2)	C30—N4—C32—C33	−173.75 (15)
C6'—C5—C6—C7	−42.00 (10)	C30—N4—C32—S2	4.3 (2)
C4—C5—C6—C11	94.99 (18)	C31—S2—C32—N4	−6.67 (15)
C6'—C5—C6—C11	130.2 (2)	C31—S2—C32—C33	171.51 (14)
C11—C6—C7—C8	0.0	N4—C32—C33—C34	86.1 (2)
C5—C6—C7—C8	171.94 (17)	S2—C32—C33—C34	−91.95 (16)
C6—C7—C8—C9	0.0	C32—C33—C34—C39	−92.5 (2)
C7—C8—C9—C10	0.0	C32—C33—C34—C35	83.6 (2)
C8—C9—C10—C11	0.0	C39—C34—C35—C36	−0.2 (3)
C9—C10—C11—C6	0.0	C33—C34—C35—C36	−176.37 (17)
C7—C6—C11—C10	0.0	C34—C35—C36—C37	−0.4 (3)
C5—C6—C11—C10	−172.34 (15)	C35—C36—C37—C38	0.3 (3)
C6—C5—C6'—C7'	130.47 (13)	C36—C37—C38—C39	0.4 (3)
C4—C5—C6'—C7'	−83.98 (19)	C37—C38—C39—C34	−0.9 (3)
C6—C5—C6'—C11'	−55.0 (2)	C35—C34—C39—C38	0.8 (3)
C4—C5—C6'—C11'	90.52 (18)	C33—C34—C39—C38	177.04 (16)
C11'—C6'—C7'—C8'	0.0	C29—N3—C40—C41	−107.9 (2)
C5—C6'—C7'—C8'	174.75 (14)	C31—N3—C40—C41	105.2 (2)
C6'—C7'—C8'—C9'	0.0	C29—N3—C40—C43	73.9 (2)
C7'—C8'—C9'—C10'	0.0	C31—N3—C40—C43	−73.0 (2)
C8'—C9'—C10'—C11'	0.0	N3—C40—C41—O6	179.52 (14)
C9'—C10'—C11'—C6'	0.0	C43—C40—C41—O6	−2.3 (3)
C7'—C6'—C11'—C10'	0.0	N3—C40—C41—C42	−0.5 (3)
C5—C6'—C11'—C10'	−174.26 (15)	C43—C40—C41—C42	177.67 (16)
C1—N1—C12—C13	−82.0 (2)	C44—O8—C43—O7	−5.4 (2)
C3—N1—C12—C13	103.8 (2)	C44—O8—C43—C40	173.65 (13)
C1—N1—C12—C15	99.3 (2)	C41—C40—C43—O7	2.6 (3)
C3—N1—C12—C15	−74.9 (2)	N3—C40—C43—O7	−179.20 (15)
N1—C12—C13—O2	178.32 (15)	C41—C40—C43—O8	−176.43 (15)
C15—C12—C13—O2	−3.1 (3)	N3—C40—C43—O8	1.8 (2)
N1—C12—C13—C14	−0.9 (3)	C43—O8—C44—C51	−76.22 (17)
C15—C12—C13—C14	177.73 (17)	C43—O8—C44—C45	160.87 (13)
C16—O4—C15—O3	−3.0 (2)	O8—C44—C45—C50	3.9 (2)
C16—O4—C15—C12	176.72 (14)	C51—C44—C45—C50	−116.91 (18)
C13—C12—C15—O3	2.5 (3)	O8—C44—C45—C46	−177.76 (15)
N1—C12—C15—O3	−178.86 (15)	C51—C44—C45—C46	61.4 (2)
C13—C12—C15—O4	−177.27 (15)	C50—C45—C46—C47	1.8 (3)
N1—C12—C15—O4	1.4 (2)	C44—C45—C46—C47	−176.59 (18)
C15—O4—C16—C17	158.61 (14)	C45—C46—C47—C48	0.8 (3)
C15—O4—C16—C23	−78.44 (17)	C46—C47—C48—C49	−2.4 (3)
O4—C16—C17—C22	−146.51 (16)	C47—C48—C49—C50	1.4 (3)
C23—C16—C17—C22	92.4 (2)	C46—C45—C50—C49	−2.8 (3)
O4—C16—C17—C18	36.3 (2)	C44—C45—C50—C49	175.52 (17)
C23—C16—C17—C18	−84.8 (2)	C48—C49—C50—C45	1.2 (3)
C22—C17—C18—C19	−0.4 (3)	O8—C44—C51—C56	128.17 (16)
C16—C17—C18—C19	176.76 (17)	C45—C44—C51—C56	−112.06 (18)
C17—C18—C19—C20	−0.2 (3)	O8—C44—C51—C52	−51.2 (2)
C18—C19—C20—C21	1.1 (3)	C45—C44—C51—C52	68.5 (2)
C19—C20—C21—C22	−1.2 (3)	C56—C51—C52—C53	−1.1 (3)
C18—C17—C22—C21	0.3 (3)	C44—C51—C52—C53	178.28 (15)
C16—C17—C22—C21	−176.98 (17)	C51—C52—C53—C54	1.2 (3)
C20—C21—C22—C17	0.5 (3)	C52—C53—C54—C55	−0.1 (3)
O4—C16—C23—C28	142.55 (16)	C53—C54—C55—C56	−1.0 (3)
C17—C16—C23—C28	−98.3 (2)	C52—C51—C56—C55	0.0 (3)
O4—C16—C23—C24	−39.9 (2)	C44—C51—C56—C55	−179.38 (17)
C17—C16—C23—C24	79.3 (2)	C54—C55—C56—C51	1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.87 (3)	1.78 (3)	2.5688 (19)	151 (2)
O6—H6···O7	0.89 (3)	1.83 (2)	2.5975 (18)	143 (2)