Rigid backbone moiety of KNI-272, a highly selective HIV protease inhibitor: methanol, acetone and dimethylsulfoxide solvated forms of 3-[3-benzyl-2-hydroxy-9-(isoquinolin-5-yloxy)-6-methylsulfanylmethyl-5,8-dioxo-4,7-diazanonanoyl]-N-tert-butyl-1,3-thiazolidine-4-carboxamide

When crystals of kynostatin (KNI)-272, a highly selective HIV protease inhibitor containing allophenylnorstatine [(2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid], were grown in three different solvent systems (methanol, acetone and dimethylsulfoxide solutions), the local conformations around the hydroxymethylcarbonyl (HMC) moiety, which mimics the structure of the transition state, were similar in all three forms. The peptide backbones were slightly bent, but their structures differed from typical sheets, turns or helixes. Although the isoquinoline ring at the N-terminal showed conformational variations, a remarkable similarity was observed in the C-terminal region, including the HMC moiety. Moreover, the conformational characteristics of the uncomplexed forms resembled those of the inhibitor within the KNI-272-HIV protease complex. This suggests that the structure of the C-terminal region of KNI-272 is rigid or very stable.

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINTPLUS (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PARST (Nardelli, 1983).

Figures

(knime) HIV protease inhibitor KNI272: iQoa-Mta-Apns-Thz-tBu methanol

Crystal data

C33H41N5O6S2·CH4O	F(000) = 744
Mr = 699.87	Dx = 1.259 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.5077 (9) Å	Cell parameters from 9961 reflections
b = 13.2881 (12) Å	θ = 2.2–28.3°
c = 13.5150 (12) Å	µ = 0.20 mm^−1
β = 101.924 (1)°	T = 90 K
V = 1846.3 (3) Å^3	Block, colorless
Z = 2	0.45 × 0.22 × 0.12 mm

Data collection

Bruker AXS, SMART APEX area detector diffractometer	8028 independent reflections
Radiation source: MacScience, M18XCE rotating anode	7717 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.366 pixels mm^-1	θmax = 27.1°, θmin = 2.2°
ω–scan	h = −13→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −17→16
Tmin = 0.898, Tmax = 1.0	l = −16→17
16068 measured reflections

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.322P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.011
8028 reflections	Δρmax = 0.34 e Å^−3
454 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack (1983), 3786 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (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)
N1_1	0.94101 (16)	0.28151 (14)	0.35820 (12)	0.0332 (4)
C2_1	0.93237 (19)	0.26127 (16)	0.45592 (15)	0.0339 (4)
H1_1	0.8629	0.2909	0.4809	0.041*
C3_1	1.01756 (18)	0.20103 (15)	0.51978 (13)	0.0272 (4)
H2_1	1.0067	0.1891	0.5869	0.033*
C4_1	1.21615 (16)	0.09126 (12)	0.54315 (12)	0.0193 (3)
C5_1	1.31546 (17)	0.05175 (13)	0.50399 (13)	0.0227 (3)
H3_1	1.3769	0.0080	0.5439	0.027*
C6_1	1.32696 (18)	0.07593 (15)	0.40391 (14)	0.0272 (4)
H4_1	1.3972	0.0491	0.3779	0.033*
C7_1	1.23869 (17)	0.13706 (15)	0.34482 (13)	0.0263 (4)
H5_1	1.2469	0.1525	0.2778	0.032*
C8_1	1.03914 (18)	0.24079 (15)	0.32599 (14)	0.0291 (4)
H6_1	1.0465	0.2550	0.2585	0.035*
C9_1	1.12239 (16)	0.15658 (12)	0.48440 (12)	0.0205 (3)
C10_1	1.13436 (16)	0.17763 (13)	0.38397 (13)	0.0224 (3)
O11_1	1.19710 (11)	0.07288 (9)	0.63905 (8)	0.0214 (2)
CA_1	1.27514 (16)	−0.00522 (12)	0.69247 (12)	0.0193 (3)
H7_1	1.3685	0.0097	0.6969	0.023*
H8_1	1.2548	−0.0701	0.6568	0.023*
C_1	1.24565 (14)	−0.01142 (11)	0.79817 (11)	0.0158 (3)
O_1	1.28286 (11)	0.05489 (8)	0.86116 (8)	0.0191 (2)
N_2	1.18485 (12)	−0.09577 (10)	0.81575 (9)	0.0153 (2)
H1_2	1.1487	−0.1336	0.7641	0.018*
CA_2	1.17621 (14)	−0.12736 (11)	0.91771 (11)	0.0142 (3)
H2_2	1.2418	−0.0897	0.9684	0.017*
CB_2	1.04137 (15)	−0.11318 (12)	0.94119 (12)	0.0172 (3)
H3_2	1.0429	−0.1386	1.0103	0.021*
H4_2	0.9785	−0.1547	0.8935	0.021*
SG_2	0.98423 (4)	0.01541 (3)	0.93325 (3)	0.02309 (9)
CD_2	1.09900 (17)	0.07242 (15)	1.03563 (16)	0.0311 (4)
H5_2	1.0787	0.1441	1.0398	0.047*
H6_2	1.1872	0.0649	1.0233	0.047*
H7_2	1.0935	0.0392	1.0994	0.047*
C_2	1.21295 (14)	−0.23976 (11)	0.92068 (11)	0.0142 (3)
O_2	1.12940 (11)	−0.30515 (8)	0.89820 (9)	0.0207 (2)
N_3	1.34142 (12)	−0.25902 (10)	0.93946 (10)	0.0151 (2)
H1_3	1.3975	−0.2126	0.9668	0.018*
CB1_3	1.38702 (14)	−0.35779 (11)	0.91403 (11)	0.0151 (3)
H2_3	1.3302	−0.3803	0.8491	0.018*
CG_3	1.52765 (15)	−0.35174 (12)	0.89819 (12)	0.0176 (3)
H3_3	1.5863	−0.3389	0.9643	0.021*
H4_3	1.5517	−0.4177	0.8735	0.021*
CD_3	1.54962 (15)	−0.27116 (12)	0.82450 (12)	0.0171 (3)
CE1_3	1.47507 (16)	−0.26719 (14)	0.72630 (13)	0.0232 (3)
H5_3	1.4069	−0.3144	0.7057	0.028*
CZ1_3	1.49942 (18)	−0.19511 (14)	0.65857 (14)	0.0283 (4)
H6_3	1.4487	−0.1940	0.5917	0.034*
CH_3	1.59760 (19)	−0.12428 (15)	0.68757 (15)	0.0300 (4)
H7_3	1.6137	−0.0748	0.6409	0.036*
CZ2_3	1.67152 (17)	−0.12653 (14)	0.78488 (15)	0.0274 (4)
H8_3	1.7385	−0.0782	0.8053	0.033*
CE2_3	1.64807 (16)	−0.19946 (12)	0.85300 (13)	0.0207 (3)
H9_3	1.6995	−0.2006	0.9196	0.025*
CA_3	1.37385 (15)	−0.43526 (11)	0.99683 (11)	0.0154 (3)
H10_3	1.2818	−0.4351	1.0059	0.018*
OB2_3	1.45616 (10)	−0.41189 (8)	1.09016 (8)	0.0181 (2)
H11_3	1.5043	−0.4633	1.1081	0.027*
C_3	1.40530 (15)	−0.53983 (11)	0.96041 (11)	0.0152 (3)
O_3	1.51282 (11)	−0.57815 (8)	0.99376 (9)	0.0186 (2)
N_4	1.31738 (12)	−0.58395 (10)	0.88763 (10)	0.0174 (3)
CA_4	1.35277 (14)	−0.67771 (11)	0.84227 (12)	0.0164 (3)
H1_4	1.3830	−0.7290	0.8962	0.020*
CB_4	1.23016 (15)	−0.71537 (12)	0.76929 (13)	0.0206 (3)
H2_4	1.2288	−0.7898	0.7666	0.025*
H3_4	1.2266	−0.6890	0.7003	0.025*
SG_4	1.09519 (4)	−0.66828 (3)	0.81963 (4)	0.02919 (11)
CD_4	1.18309 (15)	−0.55092 (13)	0.84885 (14)	0.0233 (3)
H4_4	1.1768	−0.5089	0.7876	0.028*
H5_4	1.1495	−0.5122	0.9006	0.028*
C_4	1.46038 (15)	−0.65686 (12)	0.78337 (11)	0.0176 (3)
O_4	1.45933 (12)	−0.57817 (9)	0.73512 (9)	0.0238 (2)
N_5	1.54594 (13)	−0.73163 (11)	0.78609 (10)	0.0192 (3)
H1_5	1.5364	−0.7855	0.8217	0.023*
CA_5	1.65615 (17)	−0.72972 (15)	0.73291 (14)	0.0289 (4)
CB1_5	1.6037 (2)	−0.72352 (18)	0.61858 (14)	0.0355 (4)
H2_5	1.5553	−0.6606	0.6024	0.053*
H3_5	1.5458	−0.7807	0.5968	0.053*
H4_5	1.6764	−0.7253	0.5835	0.053*
CB2_5	1.74314 (19)	−0.6394 (2)	0.77065 (17)	0.0428 (5)
H5_5	1.6941	−0.5770	0.7526	0.064*
H6_5	1.8192	−0.6400	0.7392	0.064*
H7_5	1.7718	−0.6433	0.8443	0.064*
CB3_5	1.7314 (3)	−0.8271 (2)	0.7605 (2)	0.0554 (8)
H8_5	1.6752	−0.8846	0.7358	0.083*
H9_5	1.7596	−0.8316	0.8341	0.083*
H10_5	1.8076	−0.8279	0.7293	0.083*
O1_6	1.3388 (5)	−0.4948 (3)	0.5452 (3)	0.0663 (15)	0.525 (5)
H1_6	1.3701	−0.5204	0.6035	0.080*	0.525 (5)
C1_6	1.2133 (10)	−0.5338 (9)	0.5164 (9)	0.061 (3)	0.525 (5)
H2_6	1.1607	−0.5118	0.5645	0.091*	0.525 (5)
H3_6	1.2173	−0.6075	0.5160	0.091*	0.525 (5)
H4_6	1.1736	−0.5096	0.4486	0.091*	0.525 (5)
O1'_6	1.2636 (4)	−0.4640 (3)	0.6308 (3)	0.0573 (14)	0.475 (5)
H5_6	1.3225	−0.4957	0.6746	0.069*	0.475 (5)
C1'_6	1.2229 (19)	−0.5051 (12)	0.5380 (11)	0.107 (7)	0.475 (5)
H6_6	1.1547	−0.5548	0.5405	0.161*	0.475 (5)
H7_6	1.2964	−0.5381	0.5169	0.161*	0.475 (5)
H8_6	1.1882	−0.4521	0.4895	0.161*	0.475 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1_1	0.0310 (8)	0.0397 (9)	0.0290 (8)	0.0120 (7)	0.0064 (6)	0.0129 (7)
C2_1	0.0298 (9)	0.0416 (12)	0.0325 (10)	0.0160 (8)	0.0113 (8)	0.0119 (8)
C3_1	0.0282 (9)	0.0320 (9)	0.0233 (9)	0.0083 (7)	0.0095 (7)	0.0081 (7)
C4_1	0.0226 (8)	0.0166 (7)	0.0186 (7)	−0.0009 (6)	0.0037 (6)	0.0016 (6)
C5_1	0.0231 (8)	0.0214 (8)	0.0235 (8)	0.0027 (6)	0.0044 (6)	0.0044 (6)
C6_1	0.0278 (9)	0.0294 (10)	0.0280 (9)	0.0030 (7)	0.0140 (7)	0.0039 (7)
C7_1	0.0282 (9)	0.0308 (9)	0.0224 (8)	0.0013 (7)	0.0109 (7)	0.0057 (7)
C8_1	0.0311 (9)	0.0350 (10)	0.0214 (8)	0.0033 (8)	0.0061 (7)	0.0100 (7)
C9_1	0.0211 (8)	0.0194 (8)	0.0208 (8)	0.0009 (6)	0.0042 (6)	0.0028 (6)
C10_1	0.0241 (8)	0.0224 (8)	0.0211 (8)	−0.0006 (7)	0.0056 (6)	0.0042 (6)
O11_1	0.0264 (6)	0.0203 (6)	0.0181 (5)	0.0084 (5)	0.0059 (4)	0.0062 (4)
CA_1	0.0213 (8)	0.0164 (8)	0.0208 (8)	0.0038 (6)	0.0057 (6)	0.0041 (6)
C_1	0.0137 (7)	0.0154 (7)	0.0172 (7)	0.0044 (5)	0.0010 (5)	0.0037 (5)
O_1	0.0194 (5)	0.0150 (5)	0.0216 (6)	−0.0006 (4)	0.0014 (4)	0.0009 (4)
N_2	0.0163 (6)	0.0138 (6)	0.0153 (6)	−0.0001 (5)	0.0019 (5)	0.0000 (5)
CA_2	0.0141 (7)	0.0123 (7)	0.0162 (7)	0.0017 (5)	0.0031 (5)	−0.0003 (5)
CB_2	0.0137 (7)	0.0164 (7)	0.0219 (8)	0.0030 (5)	0.0047 (6)	−0.0009 (6)
SG_2	0.01559 (18)	0.01967 (19)	0.0335 (2)	0.00575 (15)	0.00394 (15)	−0.00379 (16)
CD_2	0.0205 (8)	0.0296 (10)	0.0440 (11)	−0.0006 (7)	0.0086 (7)	−0.0175 (8)
C_2	0.0139 (7)	0.0133 (7)	0.0161 (7)	0.0013 (5)	0.0048 (5)	0.0015 (5)
O_2	0.0152 (5)	0.0148 (5)	0.0316 (6)	−0.0016 (4)	0.0041 (4)	0.0006 (5)
N_3	0.0134 (6)	0.0114 (6)	0.0207 (6)	0.0005 (5)	0.0039 (5)	−0.0015 (5)
CB1_3	0.0148 (7)	0.0116 (7)	0.0192 (7)	0.0012 (5)	0.0046 (6)	−0.0007 (6)
CG_3	0.0143 (7)	0.0170 (8)	0.0223 (8)	0.0019 (6)	0.0058 (6)	0.0007 (6)
CD_3	0.0161 (7)	0.0158 (7)	0.0218 (7)	0.0022 (6)	0.0097 (6)	−0.0003 (6)
CE1_3	0.0192 (8)	0.0270 (8)	0.0247 (8)	0.0011 (6)	0.0072 (6)	−0.0012 (7)
CZ1_3	0.0277 (9)	0.0341 (10)	0.0241 (8)	0.0067 (7)	0.0074 (7)	0.0058 (7)
CH_3	0.0310 (9)	0.0271 (9)	0.0363 (10)	0.0066 (7)	0.0173 (8)	0.0132 (8)
CZ2_3	0.0230 (9)	0.0203 (8)	0.0420 (10)	−0.0011 (7)	0.0137 (8)	0.0032 (7)
CE2_3	0.0179 (8)	0.0197 (8)	0.0260 (8)	0.0010 (6)	0.0076 (6)	−0.0019 (6)
CA_3	0.0159 (7)	0.0116 (7)	0.0194 (7)	0.0006 (5)	0.0055 (5)	0.0000 (5)
OB2_3	0.0195 (5)	0.0149 (5)	0.0198 (5)	0.0023 (4)	0.0037 (4)	−0.0010 (4)
C_3	0.0156 (7)	0.0127 (7)	0.0186 (7)	0.0014 (5)	0.0061 (6)	0.0023 (5)
O_3	0.0162 (5)	0.0143 (5)	0.0246 (6)	0.0025 (4)	0.0026 (4)	0.0010 (4)
N_4	0.0150 (6)	0.0133 (6)	0.0238 (6)	0.0031 (5)	0.0035 (5)	−0.0024 (5)
CA_4	0.0174 (7)	0.0114 (7)	0.0215 (7)	0.0016 (6)	0.0062 (6)	−0.0013 (6)
CB_4	0.0176 (7)	0.0172 (8)	0.0276 (8)	−0.0005 (6)	0.0060 (6)	−0.0060 (6)
SG_4	0.01665 (19)	0.0297 (2)	0.0426 (3)	−0.00515 (17)	0.00935 (17)	−0.0134 (2)
CD_4	0.0140 (8)	0.0194 (8)	0.0344 (9)	0.0038 (6)	0.0001 (7)	−0.0076 (7)
C_4	0.0173 (7)	0.0160 (7)	0.0186 (7)	−0.0010 (6)	0.0019 (6)	−0.0006 (6)
O_4	0.0266 (6)	0.0172 (6)	0.0283 (6)	−0.0004 (5)	0.0074 (5)	0.0056 (5)
N_5	0.0193 (6)	0.0180 (6)	0.0228 (7)	0.0029 (5)	0.0097 (5)	0.0050 (5)
CA_5	0.0206 (8)	0.0379 (10)	0.0320 (9)	0.0102 (7)	0.0140 (7)	0.0124 (8)
CB1_5	0.0375 (11)	0.0442 (12)	0.0291 (10)	0.0073 (9)	0.0169 (8)	0.0015 (9)
CB2_5	0.0202 (9)	0.0660 (16)	0.0407 (11)	−0.0091 (9)	0.0026 (8)	0.0176 (11)
CB3_5	0.0485 (14)	0.0604 (16)	0.0714 (16)	0.0370 (12)	0.0446 (13)	0.0351 (13)
O1_6	0.067 (3)	0.064 (3)	0.055 (2)	−0.024 (2)	−0.0162 (19)	0.0290 (19)
C1_6	0.047 (4)	0.075 (6)	0.055 (5)	−0.006 (4)	−0.005 (3)	0.012 (4)
O1'_6	0.057 (2)	0.034 (2)	0.068 (3)	0.0153 (16)	−0.0139 (19)	−0.0001 (17)
C1'_6	0.154 (14)	0.093 (10)	0.063 (7)	0.079 (10)	−0.005 (8)	0.015 (6)

Geometric parameters (Å, º)

N1_1—C8_1	1.316 (2)	CZ1_3—CH_3	1.392 (3)
N1_1—C2_1	1.369 (2)	CZ1_3—H6_3	0.9500
C2_1—C3_1	1.367 (2)	CH_3—CZ2_3	1.383 (3)
C2_1—H1_1	0.9500	CH_3—H7_3	0.9500
C3_1—C9_1	1.417 (2)	CZ2_3—CE2_3	1.393 (2)
C3_1—H2_1	0.9500	CZ2_3—H8_3	0.9500
C4_1—C5_1	1.369 (2)	CE2_3—H9_3	0.9500
C4_1—O11_1	1.374 (2)	CA_3—OB2_3	1.409 (2)
C4_1—C9_1	1.425 (2)	CA_3—C_3	1.533 (2)
C5_1—C6_1	1.419 (2)	CA_3—H10_3	1.0000
C5_1—H3_1	0.9500	OB2_3—H11_3	0.855
C6_1—C7_1	1.361 (3)	C_3—O_3	1.236 (2)
C6_1—H4_1	0.9500	C_3—N_4	1.338 (2)
C7_1—C10_1	1.418 (2)	N_4—CD_4	1.467 (2)
C7_1—H5_1	0.9500	N_4—CA_4	1.470 (2)
C8_1—C10_1	1.413 (2)	CA_4—CB_4	1.536 (2)
C8_1—H6_1	0.9500	CA_4—C_4	1.536 (2)
C9_1—C10_1	1.417 (2)	CA_4—H1_4	1.0000
O11_1—CA_1	1.423 (2)	CB_4—SG_4	1.807 (2)
CA_1—C_1	1.525 (2)	CB_4—H2_4	0.9900
CA_1—H7_1	0.9900	CB_4—H3_4	0.9900
CA_1—H8_1	0.9900	SG_4—CD_4	1.814 (2)
C_1—O_1	1.231 (2)	CD_4—H4_4	0.9900
C_1—N_2	1.336 (2)	CD_4—H5_4	0.9900
N_2—CA_2	1.461 (2)	C_4—O_4	1.231 (2)
N_2—H1_2	0.8800	C_4—N_5	1.335 (2)
CA_2—CB_2	1.526 (2)	N_5—CA_5	1.484 (2)
CA_2—C_2	1.541 (2)	N_5—H1_5	0.8800
CA_2—H2_2	1.0000	CA_5—CB3_5	1.522 (3)
CB_2—SG_2	1.807 (2)	CA_5—CB2_5	1.531 (3)
CB_2—H3_2	0.9900	CA_5—CB1_5	1.532 (3)
CB_2—H4_2	0.9900	CB1_5—H2_5	0.9800
SG_2—CD_2	1.804 (2)	CB1_5—H3_5	0.9800
CD_2—H5_2	0.9800	CB1_5—H4_5	0.9800
CD_2—H6_2	0.9800	CB2_5—H5_5	0.9800
CD_2—H7_2	0.9800	CB2_5—H6_5	0.9800
C_2—O_2	1.228 (2)	CB2_5—H7_5	0.9800
C_2—N_3	1.346 (2)	CB3_5—H8_5	0.9800
N_3—CB1_3	1.462 (2)	CB3_5—H9_5	0.9800
N_3—H1_3	0.8800	CB3_5—H10_5	0.9800
CB1_3—CG_3	1.538 (2)	O1_6—C1_6	1.40 (1)
CB1_3—CA_3	1.548 (2)	O1_6—H1_6	0.859
CB1_3—H2_3	1.0000	C1_6—H2_6	0.9800
CG_3—CD_3	1.512 (2)	C1_6—H3_6	0.9800
CG_3—H3_3	0.9900	C1_6—H4_6	0.9800
CG_3—H4_3	0.9900	O1'_6—C1'_6	1.35 (2)
CD_3—CE1_3	1.396 (2)	O1'_6—H5_6	0.871
CD_3—CE2_3	1.400 (2)	C1'_6—H6_6	0.9800
CE1_3—CZ1_3	1.385 (3)	C1'_6—H7_6	0.9800
CE1_3—H5_3	0.9500	C1'_6—H8_6	0.9800
C8_1—N1_1—C2_1	116.8 (2)	CD_3—CE1_3—H5_3	119.6
C3_1—C2_1—N1_1	124.0 (2)	CE1_3—CZ1_3—CH_3	120.6 (2)
C3_1—C2_1—H1_1	118.0	CE1_3—CZ1_3—H6_3	119.7
N1_1—C2_1—H1_1	118.0	CH_3—CZ1_3—H6_3	119.7
C2_1—C3_1—C9_1	119.0 (2)	CZ2_3—CH_3—CZ1_3	119.4 (2)
C2_1—C3_1—H2_1	120.5	CZ2_3—CH_3—H7_3	120.3
C9_1—C3_1—H2_1	120.5	CZ1_3—CH_3—H7_3	120.3
C5_1—C4_1—O11_1	124.6 (2)	CH_3—CZ2_3—CE2_3	120.2 (2)
C5_1—C4_1—C9_1	120.8 (2)	CH_3—CZ2_3—H8_3	119.9
O11_1—C4_1—C9_1	114.5 (1)	CE2_3—CZ2_3—H8_3	119.9
C4_1—C5_1—C6_1	120.2 (2)	CZ2_3—CE2_3—CD_3	120.9 (2)
C4_1—C5_1—H3_1	119.9	CZ2_3—CE2_3—H9_3	119.6
C6_1—C5_1—H3_1	119.9	CD_3—CE2_3—H9_3	119.6
C7_1—C6_1—C5_1	120.8 (2)	OB2_3—CA_3—C_3	110.7 (1)
C7_1—C6_1—H4_1	119.6	OB2_3—CA_3—CB1_3	111.8 (1)
C5_1—C6_1—H4_1	119.6	C_3—CA_3—CB1_3	108.3 (1)
C6_1—C7_1—C10_1	119.6 (2)	OB2_3—CA_3—H10_3	108.7
C6_1—C7_1—H5_1	120.2	C_3—CA_3—H10_3	108.7
C10_1—C7_1—H5_1	120.2	CB1_3—CA_3—H10_3	108.7
N1_1—C8_1—C10_1	125.1 (2)	CA_3—OB2_3—H11_3	107.2
N1_1—C8_1—H6_1	117.5	O_3—C_3—N_4	121.9 (1)
C10_1—C8_1—H6_1	117.5	O_3—C_3—CA_3	119.9 (1)
C10_1—C9_1—C3_1	118.0 (2)	N_4—C_3—CA_3	118.1 (1)
C10_1—C9_1—C4_1	117.8 (2)	C_3—N_4—CD_4	126.8 (1)
C3_1—C9_1—C4_1	124.2 (2)	C_3—N_4—CA_4	118.8 (1)
C8_1—C10_1—C9_1	117.1 (2)	CD_4—N_4—CA_4	114.3 (1)
C8_1—C10_1—C7_1	122.2 (2)	N_4—CA_4—CB_4	107.0 (1)
C9_1—C10_1—C7_1	120.7 (2)	N_4—CA_4—C_4	109.9 (1)
C4_1—O11_1—CA_1	115.3 (1)	CB_4—CA_4—C_4	109.6 (1)
O11_1—CA_1—C_1	107.9 (1)	N_4—CA_4—H1_4	110.1
O11_1—CA_1—H7_1	110.1	CB_4—CA_4—H1_4	110.1
C_1—CA_1—H7_1	110.1	C_4—CA_4—H1_4	110.1
O11_1—CA_1—H8_1	110.1	CA_4—CB_4—SG_4	105.4 (1)
C_1—CA_1—H8_1	110.1	CA_4—CB_4—H2_4	110.7
H7_1—CA_1—H8_1	108.4	SG_4—CB_4—H2_4	110.7
O_1—C_1—N_2	124.9 (1)	CA_4—CB_4—H3_4	110.7
O_1—C_1—CA_1	120.8 (1)	SG_4—CB_4—H3_4	110.7
N_2—C_1—CA_1	114.2 (1)	H2_4—CB_4—H3_4	108.8
C_1—N_2—CA_2	122.3 (1)	CB_4—SG_4—CD_4	88.61 (8)
C_1—N_2—H1_2	118.9	N_4—CD_4—SG_4	103.3 (1)
CA_2—N_2—H1_2	118.9	N_4—CD_4—H4_4	111.1
N_2—CA_2—CB_2	113.7 (1)	SG_4—CD_4—H4_4	111.1
N_2—CA_2—C_2	103.8 (1)	N_4—CD_4—H5_4	111.1
CB_2—CA_2—C_2	110.7 (1)	SG_4—CD_4—H5_4	111.1
N_2—CA_2—H2_2	109.5	H4_4—CD_4—H5_4	109.1
CB_2—CA_2—H2_2	109.5	O_4—C_4—N_5	125.4 (2)
C_2—CA_2—H2_2	109.5	O_4—C_4—CA_4	120.0 (1)
CA_2—CB_2—SG_2	114.6 (1)	N_5—C_4—CA_4	114.5 (1)
CA_2—CB_2—H3_2	108.6	C_4—N_5—CA_5	124.2 (1)
SG_2—CB_2—H3_2	108.6	C_4—N_5—H1_5	117.9
CA_2—CB_2—H4_2	108.6	CA_5—N_5—H1_5	117.9
SG_2—CB_2—H4_2	108.6	N_5—CA_5—CB3_5	106.5 (2)
H3_2—CB_2—H4_2	107.6	N_5—CA_5—CB2_5	108.9 (2)
CD_2—SG_2—CB_2	100.97 (8)	CB3_5—CA_5—CB2_5	109.9 (2)
SG_2—CD_2—H5_2	109.5	N_5—CA_5—CB1_5	109.6 (2)
SG_2—CD_2—H6_2	109.5	CB3_5—CA_5—CB1_5	110.7 (2)
H5_2—CD_2—H6_2	109.5	CB2_5—CA_5—CB1_5	111.1 (2)
SG_2—CD_2—H7_2	109.5	CA_5—CB1_5—H2_5	109.5
H5_2—CD_2—H7_2	109.5	CA_5—CB1_5—H3_5	109.5
H6_2—CD_2—H7_2	109.5	H2_5—CB1_5—H3_5	109.5
O_2—C_2—N_3	123.4 (1)	CA_5—CB1_5—H4_5	109.5
O_2—C_2—CA_2	121.1 (1)	H2_5—CB1_5—H4_5	109.5
N_3—C_2—CA_2	115.2 (1)	H3_5—CB1_5—H4_5	109.5
C_2—N_3—CB1_3	119.4 (1)	CA_5—CB2_5—H5_5	109.5
C_2—N_3—H1_3	120.3	CA_5—CB2_5—H6_5	109.5
CB1_3—N_3—H1_3	120.3	H5_5—CB2_5—H6_5	109.5
N_3—CB1_3—CG_3	110.9 (1)	CA_5—CB2_5—H7_5	109.5
N_3—CB1_3—CA_3	110.2 (1)	H5_5—CB2_5—H7_5	109.5
CG_3—CB1_3—CA_3	111.6 (1)	H6_5—CB2_5—H7_5	109.5
N_3—CB1_3—H2_3	108.0	CA_5—CB3_5—H8_5	109.5
CG_3—CB1_3—H2_3	108.0	CA_5—CB3_5—H9_5	109.5
CA_3—CB1_3—H2_3	108.0	H8_5—CB3_5—H9_5	109.5
CD_3—CG_3—CB1_3	114.2 (1)	CA_5—CB3_5—H10_5	109.5
CD_3—CG_3—H3_3	108.7	H8_5—CB3_5—H10_5	109.5
CB1_3—CG_3—H3_3	108.7	H9_5—CB3_5—H10_5	109.5
CD_3—CG_3—H4_3	108.7	C1_6—O1_6—H1_6	105.7
CB1_3—CG_3—H4_3	108.7	C1'_6—O1'_6—H5_6	118.6
H3_3—CG_3—H4_3	107.6	O1'_6—C1'_6—H6_6	109.5
CE1_3—CD_3—CE2_3	118.3 (2)	O1'_6—C1'_6—H7_6	109.5
CE1_3—CD_3—CG_3	121.4 (1)	H6_6—C1'_6—H7_6	109.5
CE2_3—CD_3—CG_3	120.3 (1)	O1'_6—C1'_6—H8_6	109.5
CZ1_3—CE1_3—CD_3	120.7 (2)	H6_6—C1'_6—H8_6	109.5
CZ1_3—CE1_3—H5_3	119.6	H7_6—C1'_6—H8_6	109.5
C8_1—N1_1—C2_1—C3_1	−1.0 (3)	CA_3—CB1_3—CG_3—CD_3	−175.1 (1)
N1_1—C2_1—C3_1—C9_1	0.4 (3)	CB1_3—CG_3—CD_3—CE1_3	−55.0 (2)
O11_1—C4_1—C5_1—C6_1	−179.7 (2)	CB1_3—CG_3—CD_3—CE2_3	126.3 (2)
C9_1—C4_1—C5_1—C6_1	0.4 (3)	CE2_3—CD_3—CE1_3—CZ1_3	1.0 (2)
C4_1—C5_1—C6_1—C7_1	−1.2 (3)	CG_3—CD_3—CE1_3—CZ1_3	−177.7 (2)
C5_1—C6_1—C7_1—C10_1	0.4 (3)	CD_3—CE1_3—CZ1_3—CH_3	−0.9 (3)
C2_1—N1_1—C8_1—C10_1	0.7 (3)	CE1_3—CZ1_3—CH_3—CZ2_3	0.3 (3)
C2_1—C3_1—C9_1—C10_1	0.5 (3)	CZ1_3—CH_3—CZ2_3—CE2_3	0.3 (3)
C2_1—C3_1—C9_1—C4_1	−179.0 (2)	CH_3—CZ2_3—CE2_3—CD_3	−0.2 (3)
C5_1—C4_1—C9_1—C10_1	1.1 (2)	CE1_3—CD_3—CE2_3—CZ2_3	−0.4 (2)
O11_1—C4_1—C9_1—C10_1	−178.9 (2)	CG_3—CD_3—CE2_3—CZ2_3	178.3 (2)
C5_1—C4_1—C9_1—C3_1	−179.5 (2)	N_3—CB1_3—CA_3—OB2_3	−65.2 (2)
O11_1—C4_1—C9_1—C3_1	0.6 (2)	CG_3—CB1_3—CA_3—OB2_3	58.4 (2)
N1_1—C8_1—C10_1—C9_1	0.2 (3)	N_3—CB1_3—CA_3—C_3	172.6 (1)
N1_1—C8_1—C10_1—C7_1	−179.3 (2)	CG_3—CB1_3—CA_3—C_3	−63.8 (2)
C3_1—C9_1—C10_1—C8_1	−0.8 (3)	OB2_3—CA_3—C_3—O_3	−20.9 (2)
C4_1—C9_1—C10_1—C8_1	178.7 (2)	CB1_3—CA_3—C_3—O_3	101.9 (2)
C3_1—C9_1—C10_1—C7_1	178.7 (2)	OB2_3—CA_3—C_3—N_4	163.6 (1)
C4_1—C9_1—C10_1—C7_1	−1.8 (3)	CB1_3—CA_3—C_3—N_4	−73.6 (2)
C6_1—C7_1—C10_1—C8_1	−179.4 (2)	O_3—C_3—N_4—CD_4	173.8 (2)
C6_1—C7_1—C10_1—C9_1	1.1 (3)	CA_3—C_3—N_4—CD_4	−10.7 (2)
C5_1—C4_1—O11_1—CA_1	−10.5 (2)	O_3—C_3—N_4—CA_4	−3.5 (2)
C9_1—C4_1—O11_1—CA_1	169.5 (1)	CA_3—C_3—N_4—CA_4	171.9 (1)
C4_1—O11_1—CA_1—C_1	177.4 (1)	C_3—N_4—CA_4—CB_4	174.9 (1)
O11_1—CA_1—C_1—O_1	−71.4 (2)	CD_4—N_4—CA_4—CB_4	−2.8 (2)
O11_1—CA_1—C_1—N_2	112.3 (1)	C_3—N_4—CA_4—C_4	−66.2 (2)
O_1—C_1—N_2—CA_2	−11.3 (2)	CD_4—N_4—CA_4—C_4	116.1 (2)
CA_1—C_1—N_2—CA_2	164.8 (1)	N_4—CA_4—CB_4—SG_4	−28.0 (2)
C_1—N_2—CA_2—CB_2	106.3 (2)	C_4—CA_4—CB_4—SG_4	−147.1 (1)
C_1—N_2—CA_2—C_2	−133.4 (1)	CA_4—CB_4—SG_4—CD_4	40.3 (1)
N_2—CA_2—CB_2—SG_2	−60.5 (2)	C_3—N_4—CD_4—SG_4	−145.5 (1)
C_2—CA_2—CB_2—SG_2	−176.9 (1)	CA_4—N_4—CD_4—SG_4	31.9 (2)
CA_2—CB_2—SG_2—CD_2	−65.5 (1)	CB_4—SG_4—CD_4—N_4	−40.9 (1)
N_2—CA_2—C_2—O_2	−91.9 (2)	N_4—CA_4—C_4—O_4	−37.7 (2)
CB_2—CA_2—C_2—O_2	30.5 (2)	CB_4—CA_4—C_4—O_4	79.7 (2)
N_2—CA_2—C_2—N_3	81.9 (2)	N_4—CA_4—C_4—N_5	145.5 (1)
CB_2—CA_2—C_2—N_3	−155.8 (1)	CB_4—CA_4—C_4—N_5	−97.2 (2)
O_2—C_2—N_3—CB1_3	12.1 (2)	O_4—C_4—N_5—CA_5	1.8 (3)
CA_2—C_2—N_3—CB1_3	−161.4 (1)	CA_4—C_4—N_5—CA_5	178.5 (2)
C_2—N_3—CB1_3—CG_3	156.0 (1)	C_4—N_5—CA_5—CB3_5	177.4 (2)
C_2—N_3—CB1_3—CA_3	−80.0 (2)	C_4—N_5—CA_5—CB2_5	58.9 (2)
N_3—CB1_3—CG_3—CD_3	−52.0 (2)	C_4—N_5—CA_5—CB1_5	−62.8 (2)

(knidm1) HIV protease inhibitor KNI272: iQoa-Mta-Apns-Thz-tBu dimethylsuloxide

Crystal data

C33H41N5O6S2·(C2H6SO)	F(000) = 1584
Mr = 745.96	Dx = 1.268 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 29.390 (6) Å	Cell parameters from 7694 reflections
b = 12.882 (3) Å	θ = 2.5–28.2°
c = 10.609 (2) Å	µ = 0.24 mm^−1
β = 103.373 (3)°	T = 90 K
V = 3907.6 (13) Å^3	Plate, colourless
Z = 4	0.40 × 0.35 × 0.15 mm

Data collection

Bruker AXS, SMART APEX area detector diffractometer	7717 independent reflections
Radiation source: MacScience, M18XCE rotating anode	6929 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.366 pixels mm^-1	θmax = 26.7°, θmin = 2.0°
ω–scan	h = −37→37
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −16→16
Tmin = 0.598, Tmax = 1.0	l = −13→12
12220 measured reflections

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0777P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.009
7717 reflections	Δρmax = 0.84 e Å^−3
457 parameters	Δρmin = −0.48 e Å^−3
1 restraint	Absolute structure: Flack (1983), 3426 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (6)

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_1	1.02536 (9)	−0.5563 (2)	0.8583 (2)	0.0282 (5)
C2_1	0.98119 (10)	−0.5277 (2)	0.7962 (3)	0.0263 (6)
H1_1	0.9594	−0.5810	0.7628	0.032*
C3_1	0.96637 (9)	−0.4272 (2)	0.7792 (2)	0.0212 (5)
H2_1	0.9349	−0.4124	0.7366	0.025*
C4_1	0.98541 (9)	−0.2385 (2)	0.8116 (2)	0.0201 (5)
C5_1	1.01892 (9)	−0.1627 (2)	0.8470 (3)	0.0238 (6)
H3_1	1.0108	−0.0915	0.8339	0.029*
C6_1	1.06582 (10)	−0.1921 (2)	0.9035 (3)	0.0265 (6)
H4_1	1.0891	−0.1399	0.9259	0.032*
C7_1	1.07805 (10)	−0.2929 (2)	0.9260 (2)	0.0260 (6)
H5_1	1.1092	−0.3105	0.9689	0.031*
C8_1	1.05498 (10)	−0.4794 (2)	0.8996 (2)	0.0256 (6)
H6_1	1.0860	−0.4978	0.9424	0.031*
C9_1	0.99770 (9)	−0.3453 (2)	0.8247 (2)	0.0188 (5)
C10_1	1.04448 (9)	−0.3719 (2)	0.8856 (2)	0.0212 (6)
O11_1	0.93869 (6)	−0.22046 (15)	0.76374 (19)	0.0240 (4)
CA_1	0.92336 (9)	−0.1169 (2)	0.7768 (3)	0.0224 (6)
H7_1	0.9310	−0.0723	0.7084	0.027*
H8_1	0.9394	−0.0884	0.8622	0.027*
C_1	0.87093 (9)	−0.1182 (2)	0.7646 (2)	0.0199 (5)
O_1	0.84474 (7)	−0.17831 (16)	0.69161 (18)	0.0276 (4)
N_2	0.85664 (7)	−0.04619 (17)	0.83750 (19)	0.0170 (4)
H1_2	0.8780	−0.0119	0.8942	0.020*
CA_2	0.80760 (9)	−0.02151 (19)	0.8280 (2)	0.0166 (5)
H2_2	0.7873	−0.0645	0.7587	0.020*
CB_2	0.79374 (10)	−0.0383 (2)	0.9565 (2)	0.0227 (6)
H3_2	0.7621	−0.0092	0.9497	0.027*
H4_2	0.8157	0.0007	1.0250	0.027*
SG_2	0.79359 (2)	−0.17316 (5)	1.00555 (7)	0.02547 (16)
CD_2	0.74211 (12)	−0.2185 (3)	0.8908 (3)	0.0346 (7)
H5_2	0.7156	−0.1734	0.8942	0.052*
H6_2	0.7351	−0.2897	0.9126	0.052*
H7_2	0.7477	−0.2169	0.8033	0.052*
C_2	0.80294 (8)	0.09361 (19)	0.7901 (2)	0.0173 (5)
O_2	0.81358 (7)	0.16255 (15)	0.87218 (17)	0.0237 (4)
N_3	0.79126 (8)	0.11292 (17)	0.6623 (2)	0.0194 (5)
H1_3	0.7806	0.0624	0.6076	0.023*
CB1_3	0.79612 (9)	0.2169 (2)	0.6138 (2)	0.0213 (5)
H2_3	0.8239	0.2500	0.6723	0.026*
CG_3	0.80521 (10)	0.2123 (2)	0.4778 (2)	0.0260 (6)
H3_3	0.7773	0.1826	0.4179	0.031*
H4_3	0.8094	0.2839	0.4485	0.031*
CD_3	0.84729 (12)	0.1490 (2)	0.4691 (3)	0.0320 (7)
CE1_3	0.89255 (12)	0.1818 (3)	0.5306 (3)	0.0419 (8)
H5_3	0.8968	0.2447	0.5787	0.050*
CZ1_3	0.93118 (15)	0.1226 (4)	0.5217 (4)	0.0587 (12)
H6_3	0.9616	0.1452	0.5641	0.070*
CH_3	0.9258 (2)	0.0313 (4)	0.4518 (5)	0.0741 (16)
H7_3	0.9524	−0.0088	0.4463	0.089*
CZ2_3	0.8821 (3)	−0.0012 (3)	0.3907 (6)	0.0789 (18)
H8_3	0.8785	−0.0639	0.3422	0.095*
CE2_3	0.84261 (17)	0.0566 (3)	0.3985 (4)	0.0533 (11)
H9_3	0.8124	0.0328	0.3555	0.064*
CA_3	0.75265 (9)	0.2827 (2)	0.6193 (2)	0.0192 (5)
H10_3	0.7457	0.2744	0.7067	0.023*
OB2_3	0.71327 (7)	0.25110 (14)	0.52398 (19)	0.0275 (5)
H11_3	0.7048	0.3009	0.4716	0.041*
C_3	0.76401 (9)	0.3965 (2)	0.5999 (3)	0.0190 (5)
O_3	0.75156 (7)	0.43628 (14)	0.49167 (17)	0.0240 (4)
N_4	0.79103 (7)	0.44741 (16)	0.70099 (19)	0.0164 (4)
CA_4	0.81483 (9)	0.5422 (2)	0.6759 (2)	0.0175 (5)
H1_4	0.7916	0.5950	0.6316	0.021*
CB_4	0.84202 (9)	0.5830 (2)	0.8079 (2)	0.0222 (5)
H2_4	0.8421	0.6598	0.8089	0.027*
H3_4	0.8748	0.5583	0.8267	0.027*
SG_4	0.81201 (2)	0.53242 (5)	0.92603 (6)	0.02200 (15)
CD_4	0.80312 (10)	0.4124 (2)	0.8357 (2)	0.0198 (5)
H4_4	0.8320	0.3699	0.8535	0.024*
H5_4	0.7774	0.3714	0.8569	0.024*
C_4	0.84855 (9)	0.5125 (2)	0.5895 (2)	0.0197 (5)
O_4	0.87015 (7)	0.43057 (15)	0.60930 (19)	0.0273 (4)
N_5	0.84996 (10)	0.5810 (2)	0.4984 (3)	0.0392 (7)
H1_5	0.8351	0.6399	0.5016	0.047*
CA_5	0.87409 (15)	0.5688 (3)	0.3912 (4)	0.0509 (10)
CB1_5	0.92499 (14)	0.5647 (4)	0.4391 (4)	0.0629 (13)
H2_5	0.9358	0.6281	0.4882	0.094*
H3_5	0.9398	0.5592	0.3657	0.094*
H4_5	0.9334	0.5042	0.4957	0.094*
CB2_5	0.8525 (2)	0.6513 (5)	0.2908 (5)	0.0846 (17)
H5_5	0.8185	0.6425	0.2669	0.127*
H6_5	0.8651	0.6435	0.2135	0.127*
H7_5	0.8601	0.7206	0.3278	0.127*
CB3_5	0.85780 (18)	0.4634 (5)	0.3186 (4)	0.0717 (14)
H8_5	0.8689	0.4051	0.3768	0.108*
H9_5	0.8708	0.4581	0.2417	0.108*
H10_5	0.8236	0.4618	0.2922	0.108*
S1_6	1.05749 (2)	0.16033 (5)	0.92752 (7)	0.02762 (17)
O1_6	1.07410 (8)	0.05270 (15)	0.9698 (2)	0.0337 (5)
C1_6	1.06893 (11)	0.2385 (2)	1.0702 (3)	0.0303 (6)
H1_6	1.0504	0.2131	1.1297	0.045*
H2_6	1.0604	0.3107	1.0467	0.045*
H3_6	1.1023	0.2348	1.1125	0.045*
C2_6	1.10036 (12)	0.2172 (3)	0.8539 (3)	0.0350 (7)
H4_6	1.1313	0.2111	0.9128	0.052*
H5_6	1.0929	0.2906	0.8359	0.052*
H6_6	1.1004	0.1809	0.7727	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1_1	0.0280 (13)	0.0304 (13)	0.0268 (11)	0.0057 (11)	0.0079 (10)	0.0063 (10)
C2_1	0.0240 (15)	0.0289 (15)	0.0275 (13)	−0.0009 (12)	0.0093 (11)	0.0029 (11)
C3_1	0.0173 (13)	0.0275 (13)	0.0204 (12)	0.0007 (11)	0.0079 (10)	−0.0011 (10)
C4_1	0.0166 (12)	0.0262 (13)	0.0170 (11)	0.0025 (11)	0.0033 (9)	−0.0047 (10)
C5_1	0.0189 (13)	0.0249 (14)	0.0273 (13)	0.0012 (11)	0.0047 (10)	−0.0080 (11)
C6_1	0.0185 (13)	0.0350 (16)	0.0234 (13)	−0.0040 (12)	−0.0003 (10)	−0.0133 (11)
C7_1	0.0171 (13)	0.0418 (16)	0.0174 (12)	0.0048 (12)	0.0002 (10)	−0.0045 (12)
C8_1	0.0222 (14)	0.0339 (15)	0.0204 (12)	0.0103 (12)	0.0045 (10)	0.0055 (11)
C9_1	0.0146 (12)	0.0291 (13)	0.0141 (10)	0.0011 (11)	0.0060 (9)	−0.0017 (10)
C10_1	0.0180 (13)	0.0330 (15)	0.0123 (11)	0.0038 (11)	0.0031 (9)	−0.0011 (10)
O11_1	0.0143 (9)	0.0243 (10)	0.0319 (10)	0.0038 (8)	0.0023 (8)	−0.0075 (8)
CA_1	0.0198 (14)	0.0193 (13)	0.0275 (13)	0.0040 (11)	0.0045 (10)	−0.0033 (10)
C_1	0.0169 (12)	0.0216 (13)	0.0191 (12)	0.0035 (10)	0.0001 (10)	0.0031 (10)
O_1	0.0206 (9)	0.0259 (10)	0.0315 (10)	0.0050 (8)	−0.0041 (8)	−0.0097 (8)
N_2	0.0116 (10)	0.0193 (10)	0.0185 (9)	−0.0007 (8)	0.0000 (7)	−0.0023 (8)
CA_2	0.0139 (12)	0.0189 (12)	0.0166 (11)	0.0023 (10)	0.0026 (9)	0.0017 (9)
CB_2	0.0227 (14)	0.0240 (13)	0.0228 (12)	0.0011 (11)	0.0085 (10)	0.0044 (10)
SG_2	0.0216 (3)	0.0268 (3)	0.0293 (3)	0.0030 (3)	0.0084 (3)	0.0108 (3)
CD_2	0.0337 (17)	0.0310 (15)	0.0377 (16)	−0.0064 (14)	0.0055 (13)	0.0037 (13)
C_2	0.0108 (11)	0.0203 (12)	0.0207 (12)	0.0038 (10)	0.0034 (9)	0.0013 (10)
O_2	0.0277 (10)	0.0203 (9)	0.0203 (8)	0.0022 (8)	−0.0002 (7)	−0.0012 (7)
N_3	0.0228 (11)	0.0169 (10)	0.0166 (10)	−0.0006 (9)	0.0003 (8)	0.0002 (8)
CB1_3	0.0211 (14)	0.0180 (12)	0.0222 (12)	−0.0020 (11)	−0.0001 (10)	0.0006 (10)
CG_3	0.0327 (16)	0.0250 (14)	0.0199 (12)	−0.0038 (13)	0.0050 (11)	0.0003 (11)
CD_3	0.0466 (19)	0.0255 (14)	0.0310 (14)	0.0069 (14)	0.0232 (13)	0.0061 (12)
CE1_3	0.0408 (19)	0.049 (2)	0.0388 (17)	0.0148 (16)	0.0158 (14)	0.0096 (15)
CZ1_3	0.053 (3)	0.074 (3)	0.058 (2)	0.033 (2)	0.030 (2)	0.025 (2)
CH_3	0.095 (4)	0.058 (3)	0.093 (4)	0.037 (3)	0.072 (3)	0.030 (3)
CZ2_3	0.138 (5)	0.030 (2)	0.102 (4)	0.011 (3)	0.096 (4)	0.007 (2)
CE2_3	0.082 (3)	0.0266 (17)	0.070 (2)	−0.0050 (18)	0.056 (2)	−0.0033 (16)
CA_3	0.0168 (13)	0.0194 (12)	0.0178 (12)	−0.0006 (10)	−0.0033 (9)	0.0011 (9)
OB2_3	0.0234 (10)	0.0199 (9)	0.0307 (10)	−0.0042 (8)	−0.0112 (8)	0.0044 (8)
C_3	0.0154 (12)	0.0178 (11)	0.0236 (13)	0.0002 (10)	0.0036 (10)	0.0003 (9)
O_3	0.0261 (10)	0.0203 (9)	0.0207 (9)	0.0015 (8)	−0.0046 (7)	0.0048 (8)
N_4	0.0163 (10)	0.0176 (10)	0.0150 (9)	−0.0018 (9)	0.0027 (8)	0.0004 (8)
CA_4	0.0155 (12)	0.0170 (12)	0.0200 (11)	−0.0023 (10)	0.0041 (9)	0.0008 (10)
CB_4	0.0215 (13)	0.0288 (14)	0.0174 (11)	−0.0090 (11)	0.0068 (10)	−0.0017 (10)
SG_4	0.0213 (3)	0.0270 (3)	0.0190 (3)	−0.0061 (3)	0.0071 (2)	−0.0041 (3)
CD_4	0.0203 (13)	0.0195 (13)	0.0182 (12)	−0.0037 (10)	0.0015 (10)	−0.0002 (9)
C_4	0.0185 (13)	0.0222 (14)	0.0178 (11)	−0.0005 (10)	0.0031 (9)	−0.0017 (10)
O_4	0.0252 (11)	0.0253 (10)	0.0336 (10)	0.0060 (8)	0.0114 (8)	0.0054 (8)
N_5	0.0498 (17)	0.0369 (14)	0.0400 (15)	0.0187 (14)	0.0292 (13)	0.0170 (12)
CA_5	0.064 (2)	0.057 (2)	0.0434 (19)	0.028 (2)	0.0376 (18)	0.0234 (17)
CB1_5	0.046 (2)	0.113 (4)	0.0365 (18)	−0.026 (2)	0.0235 (16)	−0.011 (2)
CB2_5	0.086 (4)	0.126 (5)	0.052 (2)	0.028 (4)	0.036 (2)	0.031 (3)
CB3_5	0.065 (3)	0.112 (4)	0.042 (2)	−0.009 (3)	0.020 (2)	−0.022 (2)
S1_6	0.0208 (3)	0.0242 (3)	0.0333 (4)	0.0008 (3)	−0.0033 (3)	0.0041 (3)
O1_6	0.0294 (11)	0.0217 (10)	0.0424 (12)	−0.0007 (9)	−0.0076 (9)	0.0054 (9)
C1_6	0.0255 (16)	0.0308 (15)	0.0361 (15)	0.0036 (12)	0.0101 (12)	0.0010 (13)
C2_6	0.0388 (18)	0.0327 (16)	0.0334 (15)	0.0030 (14)	0.0083 (13)	0.0082 (13)

Geometric parameters (Å, º)

N1_1—C8_1	1.324 (4)	CZ1_3—CH_3	1.379 (7)
N1_1—C2_1	1.364 (4)	CZ1_3—H6_3	0.9500
C2_1—C3_1	1.364 (4)	CH_3—CZ2_3	1.364 (8)
C2_1—H1_1	0.9500	CH_3—H7_3	0.9500
C3_1—C9_1	1.411 (4)	CZ2_3—CE2_3	1.397 (7)
C3_1—H2_1	0.9500	CZ2_3—H8_3	0.9500
C4_1—O11_1	1.369 (3)	CE2_3—H9_3	0.9500
C4_1—C5_1	1.376 (4)	CA_3—OB2_3	1.409 (3)
C4_1—C9_1	1.421 (4)	CA_3—C_3	1.528 (4)
C5_1—C6_1	1.422 (4)	CA_3—H10_3	1.0000
C5_1—H3_1	0.9500	OB2_3—H11_3	0.848
C6_1—C7_1	1.353 (4)	C_3—O_3	1.233 (3)
C6_1—H4_1	0.9500	C_3—N_4	1.348 (3)
C7_1—C10_1	1.413 (4)	N_4—CA_4	1.462 (3)
C7_1—H5_1	0.9500	N_4—CD_4	1.462 (3)
C8_1—C10_1	1.419 (4)	CA_4—CB_4	1.535 (3)
C8_1—H6_1	0.9500	CA_4—C_4	1.546 (4)
C9_1—C10_1	1.419 (3)	CA_4—H1_4	1.0000
O11_1—CA_1	1.425 (3)	CB_4—SG_4	1.812 (3)
CA_1—C_1	1.516 (4)	CB_4—H2_4	0.9900
CA_1—H7_1	0.9900	CB_4—H3_4	0.9900
CA_1—H8_1	0.9900	SG_4—CD_4	1.806 (3)
C_1—O_1	1.231 (3)	CD_4—H4_4	0.9900
C_1—N_2	1.336 (3)	CD_4—H5_4	0.9900
N_2—CA_2	1.457 (3)	C_4—O_4	1.225 (3)
N_2—H1_2	0.8800	C_4—N_5	1.315 (4)
CA_2—CB_2	1.526 (4)	N_5—CA_5	1.482 (4)
CA_2—C_2	1.534 (3)	N_5—H1_5	0.8800
CA_2—H2_2	1.0000	CA_5—CB1_5	1.465 (6)
CB_2—SG_2	1.813 (3)	CA_5—CB2_5	1.534 (6)
CB_2—H3_2	0.9900	CA_5—CB3_5	1.580 (7)
CB_2—H4_2	0.9900	CB1_5—H2_5	0.9800
SG_2—CD_2	1.805 (3)	CB1_5—H3_5	0.9800
CD_2—H5_2	0.9800	CB1_5—H4_5	0.9800
CD_2—H6_2	0.9800	CB2_5—H5_5	0.9800
CD_2—H7_2	0.9800	CB2_5—H6_5	0.9800
C_2—O_2	1.232 (3)	CB2_5—H7_5	0.9800
C_2—N_3	1.343 (3)	CB3_5—H8_5	0.9800
N_3—CB1_3	1.454 (3)	CB3_5—H9_5	0.9800
N_3—H1_3	0.8800	CB3_5—H10_5	0.9800
CB1_3—CG_3	1.529 (4)	S1_6—O1_6	1.503 (2)
CB1_3—CA_3	1.545 (4)	S1_6—C1_6	1.784 (3)
CB1_3—H2_3	1.0000	S1_6—C2_6	1.786 (3)
CG_3—CD_3	1.502 (4)	C1_6—H1_6	0.9800
CG_3—H3_3	0.9900	C1_6—H2_6	0.9800
CG_3—H4_3	0.9900	C1_6—H3_6	0.9800
CD_3—CE2_3	1.397 (5)	C2_6—H4_6	0.9800
CD_3—CE1_3	1.404 (5)	C2_6—H5_6	0.9800
CE1_3—CZ1_3	1.389 (5)	C2_6—H6_6	0.9800
CE1_3—H5_3	0.9500
C8_1—N1_1—C2_1	115.9 (3)	CZ2_3—CH_3—CZ1_3	119.7 (4)
N1_1—C2_1—C3_1	124.0 (3)	CZ2_3—CH_3—H7_3	120.1
N1_1—C2_1—H1_1	118.0	CZ1_3—CH_3—H7_3	120.1
C3_1—C2_1—H1_1	118.0	CH_3—CZ2_3—CE2_3	120.8 (5)
C2_1—C3_1—C9_1	120.1 (3)	CH_3—CZ2_3—H8_3	119.6
C2_1—C3_1—H2_1	120.0	CE2_3—CZ2_3—H8_3	119.6
C9_1—C3_1—H2_1	120.0	CD_3—CE2_3—CZ2_3	120.4 (5)
O11_1—C4_1—C5_1	125.0 (2)	CD_3—CE2_3—H9_3	119.8
O11_1—C4_1—C9_1	114.3 (2)	CZ2_3—CE2_3—H9_3	119.8
C5_1—C4_1—C9_1	120.7 (2)	OB2_3—CA_3—C_3	110.4 (2)
C4_1—C5_1—C6_1	119.3 (3)	OB2_3—CA_3—CB1_3	111.3 (2)
C4_1—C5_1—H3_1	120.4	C_3—CA_3—CB1_3	108.2 (2)
C6_1—C5_1—H3_1	120.4	OB2_3—CA_3—H10_3	108.9
C7_1—C6_1—C5_1	121.5 (3)	C_3—CA_3—H10_3	108.9
C7_1—C6_1—H4_1	119.3	CB1_3—CA_3—H10_3	108.9
C5_1—C6_1—H4_1	119.3	CA_3—OB2_3—H11_3	108.7
C6_1—C7_1—C10_1	119.9 (2)	O_3—C_3—N_4	122.2 (2)
C6_1—C7_1—H5_1	120.0	O_3—C_3—CA_3	119.8 (2)
C10_1—C7_1—H5_1	120.0	N_4—C_3—CA_3	117.8 (2)
N1_1—C8_1—C10_1	125.8 (3)	C_3—N_4—CA_4	118.7 (2)
N1_1—C8_1—H6_1	117.1	C_3—N_4—CD_4	126.4 (2)
C10_1—C8_1—H6_1	117.1	CA_4—N_4—CD_4	114.7 (2)
C3_1—C9_1—C10_1	117.5 (2)	N_4—CA_4—CB_4	106.9 (2)
C3_1—C9_1—C4_1	124.0 (2)	N_4—CA_4—C_4	107.5 (2)
C10_1—C9_1—C4_1	118.4 (2)	CB_4—CA_4—C_4	110.8 (2)
C7_1—C10_1—C9_1	119.9 (3)	N_4—CA_4—H1_4	110.5
C7_1—C10_1—C8_1	123.5 (3)	CB_4—CA_4—H1_4	110.5
C9_1—C10_1—C8_1	116.6 (3)	C_4—CA_4—H1_4	110.5
C4_1—O11_1—CA_1	115.8 (2)	CA_4—CB_4—SG_4	105.9 (2)
O11_1—CA_1—C_1	108.6 (2)	CA_4—CB_4—H2_4	110.6
O11_1—CA_1—H7_1	110.0	SG_4—CB_4—H2_4	110.6
C_1—CA_1—H7_1	110.0	CA_4—CB_4—H3_4	110.6
O11_1—CA_1—H8_1	110.0	SG_4—CB_4—H3_4	110.6
C_1—CA_1—H8_1	110.0	H2_4—CB_4—H3_4	108.7
H7_1—CA_1—H8_1	108.3	CD_4—SG_4—CB_4	88.6 (1)
O_1—C_1—N_2	124.5 (2)	N_4—CD_4—SG_4	103.1 (2)
O_1—C_1—CA_1	122.4 (2)	N_4—CD_4—H4_4	111.1
N_2—C_1—CA_1	113.1 (2)	SG_4—CD_4—H4_4	111.1
C_1—N_2—CA_2	123.4 (2)	N_4—CD_4—H5_4	111.1
C_1—N_2—H1_2	118.3	SG_4—CD_4—H5_4	111.1
CA_2—N_2—H1_2	118.3	H4_4—CD_4—H5_4	109.1
N_2—CA_2—CB_2	111.8 (2)	O_4—C_4—N_5	127.0 (3)
N_2—CA_2—C_2	104.8 (2)	O_4—C_4—CA_4	119.3 (2)
CB_2—CA_2—C_2	110.2 (2)	N_5—C_4—CA_4	113.8 (2)
N_2—CA_2—H2_2	110.0	C_4—N_5—CA_5	126.5 (3)
CB_2—CA_2—H2_2	110.0	C_4—N_5—H1_5	116.8
C_2—CA_2—H2_2	110.0	CA_5—N_5—H1_5	116.8
CA_2—CB_2—SG_2	114.3 (2)	CB1_5—CA_5—N_5	111.6 (3)
CA_2—CB_2—H3_2	108.7	CB1_5—CA_5—CB2_5	119.4 (4)
SG_2—CB_2—H3_2	108.7	N_5—CA_5—CB2_5	105.4 (3)
CA_2—CB_2—H4_2	108.7	CB1_5—CA_5—CB3_5	108.0 (4)
SG_2—CB_2—H4_2	108.7	N_5—CA_5—CB3_5	108.7 (3)
H3_2—CB_2—H4_2	107.6	CB2_5—CA_5—CB3_5	103.1 (4)
CD_2—SG_2—CB_2	100.0 (1)	CA_5—CB1_5—H2_5	109.5
SG_2—CD_2—H5_2	109.5	CA_5—CB1_5—H3_5	109.5
SG_2—CD_2—H6_2	109.5	H2_5—CB1_5—H3_5	109.5
H5_2—CD_2—H6_2	109.5	CA_5—CB1_5—H4_5	109.5
SG_2—CD_2—H7_2	109.5	H2_5—CB1_5—H4_5	109.5
H5_2—CD_2—H7_2	109.5	H3_5—CB1_5—H4_5	109.5
H6_2—CD_2—H7_2	109.5	CA_5—CB2_5—H5_5	109.5
O_2—C_2—N_3	122.9 (2)	CA_5—CB2_5—H6_5	109.5
O_2—C_2—CA_2	121.3 (2)	H5_5—CB2_5—H6_5	109.5
N_3—C_2—CA_2	115.5 (2)	CA_5—CB2_5—H7_5	109.5
C_2—N_3—CB1_3	120.3 (2)	H5_5—CB2_5—H7_5	109.5
C_2—N_3—H1_3	119.8	H6_5—CB2_5—H7_5	109.5
CB1_3—N_3—H1_3	119.8	CA_5—CB3_5—H8_5	109.5
N_3—CB1_3—CG_3	110.5 (2)	CA_5—CB3_5—H9_5	109.5
N_3—CB1_3—CA_3	110.0 (2)	H8_5—CB3_5—H9_5	109.5
CG_3—CB1_3—CA_3	112.5 (2)	CA_5—CB3_5—H10_5	109.5
N_3—CB1_3—H2_3	107.9	H8_5—CB3_5—H10_5	109.5
CG_3—CB1_3—H2_3	107.9	H9_5—CB3_5—H10_5	109.5
CA_3—CB1_3—H2_3	107.9	O1_6—S1_6—C1_6	106.5 (1)
CD_3—CG_3—CB1_3	113.9 (2)	O1_6—S1_6—C2_6	107.2 (2)
CD_3—CG_3—H3_3	108.8	C1_6—S1_6—C2_6	97.2 (2)
CB1_3—CG_3—H3_3	108.8	S1_6—C1_6—H1_6	109.5
CD_3—CG_3—H4_3	108.8	S1_6—C1_6—H2_6	109.5
CB1_3—CG_3—H4_3	108.8	H1_6—C1_6—H2_6	109.5
H3_3—CG_3—H4_3	107.7	S1_6—C1_6—H3_6	109.5
CE2_3—CD_3—CE1_3	118.1 (3)	H1_6—C1_6—H3_6	109.5
CE2_3—CD_3—CG_3	121.0 (3)	H2_6—C1_6—H3_6	109.5
CE1_3—CD_3—CG_3	120.9 (3)	S1_6—C2_6—H4_6	109.5
CZ1_3—CE1_3—CD_3	120.3 (4)	S1_6—C2_6—H5_6	109.5
CZ1_3—CE1_3—H5_3	119.8	H4_6—C2_6—H5_6	109.5
CD_3—CE1_3—H5_3	119.8	S1_6—C2_6—H6_6	109.5
CH_3—CZ1_3—CE1_3	120.7 (5)	H4_6—C2_6—H6_6	109.5
CH_3—CZ1_3—H6_3	119.7	H5_6—C2_6—H6_6	109.5
CE1_3—CZ1_3—H6_3	119.7
C8_1—N1_1—C2_1—C3_1	−2.1 (4)	CA_3—CB1_3—CG_3—CD_3	179.9 (2)
N1_1—C2_1—C3_1—C9_1	1.3 (4)	CB1_3—CG_3—CD_3—CE2_3	113.6 (3)
O11_1—C4_1—C5_1—C6_1	175.9 (2)	CB1_3—CG_3—CD_3—CE1_3	−67.1 (4)
C9_1—C4_1—C5_1—C6_1	−3.3 (4)	CE2_3—CD_3—CE1_3—CZ1_3	−0.6 (5)
C4_1—C5_1—C6_1—C7_1	−1.6 (4)	CG_3—CD_3—CE1_3—CZ1_3	−179.9 (3)
C5_1—C6_1—C7_1—C10_1	4.1 (4)	CD_3—CE1_3—CZ1_3—CH_3	0.3 (6)
C2_1—N1_1—C8_1—C10_1	0.5 (4)	CE1_3—CZ1_3—CH_3—CZ2_3	0.1 (6)
C2_1—C3_1—C9_1—C10_1	1.1 (4)	CZ1_3—CH_3—CZ2_3—CE2_3	−0.4 (7)
C2_1—C3_1—C9_1—C4_1	−179.9 (3)	CE1_3—CD_3—CE2_3—CZ2_3	0.3 (5)
O11_1—C4_1—C9_1—C3_1	7.1 (4)	CG_3—CD_3—CE2_3—CZ2_3	179.7 (3)
C5_1—C4_1—C9_1—C3_1	−173.6 (2)	CH_3—CZ2_3—CE2_3—CD_3	0.1 (6)
O11_1—C4_1—C9_1—C10_1	−173.8 (2)	N_3—CB1_3—CA_3—OB2_3	−72.1 (3)
C5_1—C4_1—C9_1—C10_1	5.5 (4)	CG_3—CB1_3—CA_3—OB2_3	51.6 (3)
C6_1—C7_1—C10_1—C9_1	−1.7 (4)	N_3—CB1_3—CA_3—C_3	166.3 (2)
C6_1—C7_1—C10_1—C8_1	176.7 (3)	CG_3—CB1_3—CA_3—C_3	−69.9 (3)
C3_1—C9_1—C10_1—C7_1	176.2 (2)	OB2_3—CA_3—C_3—O_3	−24.6 (4)
C4_1—C9_1—C10_1—C7_1	−2.9 (4)	CB1_3—CA_3—C_3—O_3	97.5 (3)
C3_1—C9_1—C10_1—C8_1	−2.4 (3)	OB2_3—CA_3—C_3—N_4	160.9 (2)
C4_1—C9_1—C10_1—C8_1	178.5 (2)	CB1_3—CA_3—C_3—N_4	−77.0 (3)
N1_1—C8_1—C10_1—C7_1	−176.8 (3)	O_3—C_3—N_4—CA_4	−14.0 (4)
N1_1—C8_1—C10_1—C9_1	1.7 (4)	CA_3—C_3—N_4—CA_4	160.3 (2)
C5_1—C4_1—O11_1—CA_1	−13.1 (4)	O_3—C_3—N_4—CD_4	172.3 (3)
C9_1—C4_1—O11_1—CA_1	166.2 (2)	CA_3—C_3—N_4—CD_4	−13.4 (4)
C4_1—O11_1—CA_1—C_1	−160.2 (2)	C_3—N_4—CA_4—CB_4	179.2 (2)
O11_1—CA_1—C_1—O_1	−35.0 (4)	CD_4—N_4—CA_4—CB_4	−6.4 (3)
O11_1—CA_1—C_1—N_2	146.8 (2)	C_3—N_4—CA_4—C_4	−61.7 (3)
O_1—C_1—N_2—CA_2	−7.7 (4)	CD_4—N_4—CA_4—C_4	112.7 (2)
CA_1—C_1—N_2—CA_2	170.5 (2)	N_4—CA_4—CB_4—SG_4	−24.8 (2)
C_1—N_2—CA_2—CB_2	121.0 (3)	C_4—CA_4—CB_4—SG_4	−141.7 (2)
C_1—N_2—CA_2—C_2	−119.6 (2)	CA_4—CB_4—SG_4—CD_4	38.7 (2)
N_2—CA_2—CB_2—SG_2	−68.2 (3)	C_3—N_4—CD_4—SG_4	−151.7 (2)
C_2—CA_2—CB_2—SG_2	175.6 (2)	CA_4—N_4—CD_4—SG_4	34.4 (3)
CA_2—CB_2—SG_2—CD_2	−72.3 (2)	CB_4—SG_4—CD_4—N_4	−41.1 (2)
N_2—CA_2—C_2—O_2	−82.4 (3)	N_4—CA_4—C_4—O_4	−38.9 (3)
CB_2—CA_2—C_2—O_2	38.1 (3)	CB_4—CA_4—C_4—O_4	77.6 (3)
N_2—CA_2—C_2—N_3	91.2 (2)	N_4—CA_4—C_4—N_5	140.1 (2)
CB_2—CA_2—C_2—N_3	−148.4 (2)	CB_4—CA_4—C_4—N_5	−103.4 (3)
O_2—C_2—N_3—CB1_3	7.4 (4)	O_4—C_4—N_5—CA_5	7.0 (5)
CA_2—C_2—N_3—CB1_3	−166.0 (2)	CA_4—C_4—N_5—CA_5	−171.9 (3)
C_2—N_3—CB1_3—CG_3	151.4 (2)	C_4—N_5—CA_5—CB1_5	−66.7 (5)
C_2—N_3—CB1_3—CA_3	−83.7 (3)	C_4—N_5—CA_5—CB2_5	162.2 (4)
N_3—CB1_3—CG_3—CD_3	−56.6 (3)	C_4—N_5—CA_5—CB3_5	52.2 (5)

(knia) HIV protease inhibitor KNI272: iQoa-Mta-Apns-Thz-tBu diacetone

Crystal data

C33H41N5O6S2·2(C3H6O)	F(000) = 836
Mr = 783.98	Dx = 1.276 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.6395 (7) Å	Cell parameters from 7940 reflections
b = 13.2130 (9) Å	θ = 2.6–26.7°
c = 14.6921 (10) Å	µ = 0.19 mm^−1
β = 98.931 (1)°	T = 90 K
V = 2040.4 (2) Å^3	Plate, colorless
Z = 2	0.40 × 0.25 × 0.08 mm

Data collection

Bruker AXS, SMART APEX area detector diffractometer	8940 independent reflections
Radiation source: MacScience, M18XCE rotating anode	8718 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 8.366 pixels mm^-1	θmax = 27.1°, θmin = 2.5°
ω–scan	h = −13→13
Absorption correction: empirical (using intensity measurements) SADABS (Sheldrick, 1996)	k = −16→16
Tmin = 0.951, Tmax = 1.0	l = −18→18
23703 measured reflections

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0437P)^2 + 0.4323P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.007
8940 reflections	Δρmax = 0.29 e Å^−3
487 parameters	Δρmin = −0.22 e Å^−3
1 restraint	Absolute structure: Flack (1983), 4257 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

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_1	−0.07954 (14)	0.10000 (11)	−0.09446 (9)	0.0275 (3)
C2_1	0.04808 (17)	0.11322 (13)	−0.06927 (11)	0.0272 (3)
H1_1	0.1036	0.0734	−0.0994	0.033*
C3_1	0.10117 (15)	0.17999 (12)	−0.00352 (10)	0.0222 (3)
H2_1	0.1910	0.1857	0.0115	0.027*
C4_1	0.06700 (13)	0.31126 (11)	0.11277 (9)	0.0178 (3)
C5_1	−0.01681 (14)	0.36727 (11)	0.15413 (10)	0.0208 (3)
H3_1	0.0141	0.4145	0.2010	0.025*
C6_1	−0.14906 (15)	0.35463 (12)	0.12695 (11)	0.0240 (3)
H4_1	−0.2061	0.3943	0.1557	0.029*
C7_1	−0.19713 (14)	0.28687 (12)	0.06038 (11)	0.0246 (3)
H5_1	−0.2865	0.2790	0.0435	0.030*
C8_1	−0.15456 (15)	0.15623 (12)	−0.05261 (10)	0.0253 (3)
H6_1	−0.2437	0.1480	−0.0701	0.030*
C9_1	0.02067 (13)	0.24054 (10)	0.04196 (9)	0.0178 (3)
C10_1	−0.11217 (14)	0.22866 (11)	0.01697 (10)	0.0212 (3)
O11_1	0.19662 (9)	0.31441 (8)	0.13445 (7)	0.0191 (2)
CA_1	0.25102 (13)	0.39161 (11)	0.19649 (9)	0.0181 (3)
H7_1	0.2048	0.4557	0.1800	0.022*
H8_1	0.3405	0.4020	0.1876	0.022*
C_1	0.24864 (12)	0.36996 (10)	0.29779 (9)	0.0152 (3)
O_1	0.29023 (9)	0.43583 (7)	0.35413 (7)	0.0181 (2)
N_2	0.20124 (11)	0.28116 (8)	0.31976 (8)	0.0154 (2)
H1_2	0.1769	0.2369	0.2758	0.018*
CA_2	0.18856 (12)	0.25546 (10)	0.41489 (9)	0.0148 (2)
H2_2	0.2494	0.2970	0.4584	0.018*
CB_2	0.05287 (13)	0.27241 (10)	0.43412 (10)	0.0170 (3)
H3_2	0.0493	0.2527	0.4987	0.020*
H4_2	−0.0049	0.2267	0.3938	0.020*
SG_2	−0.00638 (3)	0.40015 (3)	0.41691 (2)	0.01922 (7)
CD_2	0.09446 (14)	0.46548 (12)	0.50841 (11)	0.0252 (3)
H5_2	0.0718	0.5374	0.5071	0.038*
H6_2	0.1836	0.4581	0.5000	0.038*
H7_2	0.0827	0.4364	0.5679	0.038*
C_2	0.22331 (13)	0.14280 (10)	0.42696 (9)	0.0141 (2)
O_2	0.14129 (9)	0.07678 (7)	0.41379 (7)	0.0209 (2)
N_3	0.34826 (11)	0.12283 (8)	0.44646 (8)	0.0146 (2)
H1_3	0.4020	0.1703	0.4696	0.017*
CB1_3	0.39420 (12)	0.02170 (10)	0.42900 (9)	0.0141 (2)
H2_3	0.3409	−0.0046	0.3718	0.017*
CG_3	0.53304 (13)	0.02490 (10)	0.41162 (10)	0.0171 (3)
H3_3	0.5897	0.0331	0.4713	0.020*
H4_3	0.5540	−0.0405	0.3847	0.020*
CD_3	0.55882 (13)	0.10933 (11)	0.34799 (10)	0.0171 (3)
CE1_3	0.47411 (14)	0.12963 (12)	0.26761 (10)	0.0208 (3)
H5_3	0.4021	0.0872	0.2508	0.025*
CZ1_3	0.49400 (14)	0.21116 (12)	0.21191 (10)	0.0230 (3)
H6_3	0.4357	0.2242	0.1574	0.028*
CH_3	0.59836 (15)	0.27340 (12)	0.23556 (11)	0.0255 (3)
H7_3	0.6108	0.3299	0.1980	0.031*
CZ2_3	0.68471 (15)	0.25320 (12)	0.31400 (11)	0.0255 (3)
H8_3	0.7574	0.2951	0.3297	0.031*
CE2_3	0.66517 (14)	0.17135 (12)	0.36998 (10)	0.0211 (3)
H9_3	0.7249	0.1577	0.4236	0.025*
CA_3	0.37700 (12)	−0.05090 (10)	0.50885 (9)	0.0142 (2)
H10_3	0.2863	−0.0483	0.5192	0.017*
OB2_3	0.45618 (9)	−0.02476 (7)	0.59132 (6)	0.01685 (19)
H11_3	0.5337	−0.0482	0.5959	0.020*
C_3	0.40623 (13)	−0.15728 (10)	0.47774 (9)	0.0141 (2)
O_3	0.51155 (9)	−0.19462 (7)	0.50290 (7)	0.01760 (19)
N_4	0.31776 (10)	−0.20291 (9)	0.41584 (8)	0.0152 (2)
CA_4	0.35347 (12)	−0.29276 (10)	0.36681 (9)	0.0156 (2)
H1_4	0.3837	−0.3481	0.4113	0.019*
CB_4	0.23433 (13)	−0.32591 (11)	0.30136 (10)	0.0206 (3)
H2_4	0.2327	−0.4004	0.2942	0.025*
H3_4	0.2325	−0.2947	0.2399	0.025*
SG_4	0.10020 (3)	−0.28365 (3)	0.35318 (3)	0.02303 (8)
CD_4	0.18687 (13)	−0.16853 (11)	0.38751 (11)	0.0201 (3)
H4_4	0.1814	−0.1204	0.3354	0.024*
H5_4	0.1535	−0.1354	0.4393	0.024*
C_4	0.45807 (13)	−0.26347 (10)	0.31001 (9)	0.0170 (3)
O_4	0.45038 (10)	−0.18324 (8)	0.26728 (7)	0.0236 (2)
N_5	0.54993 (11)	−0.33279 (9)	0.31061 (8)	0.0186 (2)
H1_5	0.5446	−0.3884	0.3428	0.022*
CA_5	0.65993 (14)	−0.32226 (12)	0.26080 (10)	0.0231 (3)
CB1_5	0.73310 (16)	−0.22576 (13)	0.29145 (13)	0.0305 (4)
H2_5	0.7617	−0.2281	0.3581	0.046*
H3_5	0.6775	−0.1670	0.2764	0.046*
H4_5	0.8071	−0.2201	0.2595	0.046*
CB2_5	0.74504 (17)	−0.41421 (14)	0.28837 (14)	0.0345 (4)
H5_5	0.6983	−0.4763	0.2685	0.052*
H6_5	0.7700	−0.4152	0.3554	0.052*
H7_5	0.8213	−0.4100	0.2588	0.052*
CB3_5	0.61313 (18)	−0.32189 (17)	0.15706 (12)	0.0365 (4)
H8_5	0.5664	−0.3846	0.1395	0.055*
H9_5	0.6862	−0.3171	0.1240	0.055*
H10_5	0.5568	−0.2638	0.1411	0.055*
O1_6	0.15523 (11)	0.09130 (9)	0.20515 (8)	0.0285 (2)
C1_6	0.06108 (17)	0.03804 (12)	0.19271 (10)	0.0273 (3)
C2_6	0.0623 (2)	−0.06264 (15)	0.14552 (14)	0.0458 (5)
H1_6	0.1469	−0.0750	0.1293	0.069*
H2_6	−0.0010	−0.0625	0.0894	0.069*
H3_6	0.0417	−0.1161	0.1870	0.069*
C3_6	−0.06078 (17)	0.07024 (16)	0.22283 (13)	0.0373 (4)
H4_6	−0.0492	0.1366	0.2528	0.056*
H5_6	−0.0852	0.0206	0.2664	0.056*
H6_6	−0.1277	0.0747	0.1690	0.056*
C1_7	0.4861 (2)	0.45162 (16)	−0.01770 (13)	0.0423 (5)
C2_7	0.5968 (2)	0.47560 (18)	−0.06442 (15)	0.0525 (6)
H1_7	0.6757	0.4587	−0.0235	0.079*
H2_7	0.5963	0.5479	−0.0793	0.079*
H3_7	0.5913	0.4360	−0.1213	0.079*
O1_7	0.50005 (16)	0.41811 (17)	0.05945 (11)	0.0640 (5)
C3_7	0.3584 (3)	0.4725 (2)	−0.0710 (2)	0.0744 (9)
H4_7	0.2928	0.4542	−0.0340	0.112*
H5_7	0.3468	0.4325	−0.1279	0.112*
H6_7	0.3514	0.5447	−0.0864	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1_1	0.0333 (7)	0.0258 (7)	0.0221 (6)	−0.0048 (6)	0.0003 (5)	−0.0035 (5)
C2_1	0.0345 (8)	0.0263 (8)	0.0210 (7)	0.0010 (6)	0.0052 (6)	−0.0051 (6)
C3_1	0.0241 (7)	0.0239 (7)	0.0187 (7)	−0.0012 (6)	0.0035 (5)	−0.0014 (6)
C4_1	0.0175 (6)	0.0191 (7)	0.0165 (6)	−0.0023 (5)	0.0016 (5)	0.0021 (5)
C5_1	0.0246 (7)	0.0179 (7)	0.0201 (7)	−0.0012 (5)	0.0044 (5)	0.0001 (5)
C6_1	0.0232 (7)	0.0224 (7)	0.0279 (8)	0.0033 (6)	0.0085 (6)	0.0006 (6)
C7_1	0.0186 (7)	0.0261 (8)	0.0290 (8)	−0.0008 (6)	0.0031 (6)	0.0029 (6)
C8_1	0.0258 (7)	0.0266 (8)	0.0216 (7)	−0.0055 (6)	−0.0020 (6)	0.0004 (6)
C9_1	0.0222 (7)	0.0163 (7)	0.0149 (6)	−0.0014 (5)	0.0033 (5)	0.0030 (5)
C10_1	0.0235 (7)	0.0204 (7)	0.0189 (6)	−0.0022 (6)	0.0010 (5)	0.0025 (5)
O11_1	0.0182 (5)	0.0196 (5)	0.0193 (5)	−0.0012 (4)	0.0022 (4)	−0.0023 (4)
CA_1	0.0180 (6)	0.0156 (6)	0.0205 (6)	−0.0020 (5)	0.0019 (5)	0.0013 (5)
C_1	0.0117 (6)	0.0141 (6)	0.0191 (6)	0.0025 (5)	0.0003 (5)	0.0015 (5)
O_1	0.0180 (5)	0.0136 (5)	0.0216 (5)	−0.0015 (4)	0.0001 (4)	−0.0001 (4)
N_2	0.0162 (5)	0.0126 (5)	0.0169 (5)	0.0000 (4)	0.0009 (4)	−0.0002 (4)
CA_2	0.0143 (6)	0.0122 (6)	0.0177 (6)	0.0013 (5)	0.0015 (5)	−0.0003 (5)
CB_2	0.0148 (6)	0.0131 (6)	0.0232 (7)	0.0024 (5)	0.0030 (5)	0.0016 (5)
SG_2	0.01607 (15)	0.01560 (15)	0.02542 (17)	0.00420 (12)	0.00141 (12)	−0.00091 (13)
CD_2	0.0222 (7)	0.0225 (7)	0.0305 (8)	0.0005 (6)	0.0026 (6)	−0.0092 (6)
C_2	0.0149 (6)	0.0127 (6)	0.0147 (6)	0.0000 (5)	0.0020 (5)	0.0004 (5)
O_2	0.0162 (5)	0.0144 (5)	0.0316 (5)	−0.0014 (4)	0.0018 (4)	0.0017 (4)
N_3	0.0146 (5)	0.0097 (5)	0.0190 (5)	−0.0003 (4)	0.0014 (4)	−0.0015 (4)
CB1_3	0.0143 (6)	0.0102 (6)	0.0177 (6)	0.0006 (5)	0.0017 (5)	−0.0010 (5)
CG_3	0.0149 (6)	0.0148 (6)	0.0218 (7)	0.0014 (5)	0.0039 (5)	−0.0002 (5)
CD_3	0.0174 (6)	0.0144 (6)	0.0209 (6)	0.0006 (5)	0.0071 (5)	−0.0027 (5)
CE1_3	0.0198 (7)	0.0221 (7)	0.0211 (7)	−0.0030 (5)	0.0044 (5)	−0.0030 (5)
CZ1_3	0.0228 (7)	0.0263 (7)	0.0205 (7)	0.0008 (6)	0.0051 (5)	0.0008 (6)
CH_3	0.0264 (7)	0.0222 (8)	0.0302 (8)	−0.0011 (6)	0.0117 (6)	0.0070 (6)
CZ2_3	0.0201 (7)	0.0220 (7)	0.0349 (8)	−0.0054 (6)	0.0065 (6)	0.0013 (6)
CE2_3	0.0165 (6)	0.0224 (7)	0.0245 (7)	−0.0016 (5)	0.0033 (5)	−0.0007 (6)
CA_3	0.0129 (6)	0.0114 (6)	0.0182 (6)	0.0009 (5)	0.0017 (5)	−0.0007 (5)
OB2_3	0.0165 (4)	0.0150 (5)	0.0180 (5)	0.0018 (4)	−0.0008 (4)	−0.0023 (4)
C_3	0.0153 (6)	0.0114 (6)	0.0162 (6)	0.0005 (5)	0.0037 (5)	0.0024 (5)
O_3	0.0160 (4)	0.0136 (4)	0.0225 (5)	0.0025 (4)	0.0006 (4)	0.0005 (4)
N_4	0.0147 (5)	0.0114 (5)	0.0192 (5)	0.0022 (4)	0.0017 (4)	−0.0006 (4)
CA_4	0.0171 (6)	0.0103 (6)	0.0194 (6)	0.0008 (5)	0.0029 (5)	−0.0006 (5)
CB_4	0.0184 (7)	0.0176 (6)	0.0253 (7)	−0.0004 (5)	0.0022 (6)	−0.0059 (6)
SG_4	0.01580 (16)	0.02018 (17)	0.03291 (19)	−0.00365 (13)	0.00315 (13)	−0.00711 (15)
CD_4	0.0144 (6)	0.0158 (7)	0.0286 (7)	0.0010 (5)	−0.0016 (5)	−0.0050 (5)
C_4	0.0188 (6)	0.0153 (7)	0.0162 (6)	−0.0002 (5)	0.0011 (5)	−0.0015 (5)
O_4	0.0272 (5)	0.0179 (5)	0.0265 (5)	0.0033 (4)	0.0070 (4)	0.0063 (4)
N_5	0.0201 (6)	0.0152 (6)	0.0217 (6)	0.0012 (5)	0.0072 (5)	0.0016 (5)
CA_5	0.0222 (7)	0.0245 (7)	0.0248 (7)	0.0032 (6)	0.0102 (6)	0.0022 (6)
CB1_5	0.0225 (7)	0.0301 (9)	0.0398 (9)	−0.0031 (6)	0.0074 (7)	0.0065 (7)
CB2_5	0.0304 (9)	0.0294 (9)	0.0486 (10)	0.0114 (7)	0.0212 (8)	0.0059 (8)
CB3_5	0.0385 (9)	0.0477 (11)	0.0260 (8)	−0.0003 (8)	0.0138 (7)	−0.0025 (7)
O1_6	0.0316 (6)	0.0244 (6)	0.0286 (6)	−0.0036 (5)	0.0014 (5)	−0.0009 (5)
C1_6	0.0378 (9)	0.0240 (8)	0.0183 (7)	−0.0043 (7)	−0.0016 (6)	0.0020 (6)
C2_6	0.0673 (14)	0.0307 (10)	0.0400 (10)	−0.0185 (9)	0.0104 (10)	−0.0082 (8)
C3_6	0.0287 (9)	0.0440 (11)	0.0359 (9)	−0.0057 (8)	−0.0053 (7)	−0.0012 (8)
C1_7	0.0481 (11)	0.0404 (11)	0.0349 (10)	0.0170 (9)	−0.0041 (8)	−0.0042 (8)
C2_7	0.0746 (16)	0.0455 (12)	0.0378 (11)	0.0120 (11)	0.0098 (10)	0.0148 (9)
O1_7	0.0486 (9)	0.0960 (15)	0.0478 (9)	0.0089 (9)	0.0090 (7)	0.0291 (9)
C3_7	0.0608 (16)	0.082 (2)	0.0694 (17)	0.0325 (15)	−0.0240 (13)	−0.0294 (15)

Geometric parameters (Å, º)

N1_1—C8_1	1.311 (2)	CZ2_3—CE2_3	1.394 (2)
N1_1—C2_1	1.362 (2)	CZ2_3—H8_3	0.9500
C2_1—C3_1	1.364 (2)	CE2_3—H9_3	0.9500
C2_1—H1_1	0.9500	CA_3—OB2_3	1.407 (2)
C3_1—C9_1	1.413 (2)	CA_3—C_3	1.525 (2)
C3_1—H2_1	0.9500	CA_3—H10_3	1.0000
C4_1—O11_1	1.367 (2)	OB2_3—H11_3	0.874
C4_1—C5_1	1.371 (2)	C_3—O_3	1.228 (2)
C4_1—C9_1	1.428 (2)	C_3—N_4	1.346 (2)
C5_1—C6_1	1.412 (2)	N_4—CD_4	1.463 (2)
C5_1—H3_1	0.9500	N_4—CA_4	1.469 (2)
C6_1—C7_1	1.365 (2)	CA_4—CB_4	1.531 (2)
C6_1—H4_1	0.9500	CA_4—C_4	1.541 (2)
C7_1—C10_1	1.412 (2)	CA_4—H1_4	1.0000
C7_1—H5_1	0.9500	CB_4—SG_4	1.807 (2)
C8_1—C10_1	1.422 (2)	CB_4—H2_4	0.9900
C8_1—H6_1	0.9500	CB_4—H3_4	0.9900
C9_1—C10_1	1.413 (2)	SG_4—CD_4	1.810 (2)
O11_1—CA_1	1.429 (2)	CD_4—H4_4	0.9900
CA_1—C_1	1.520 (2)	CD_4—H5_4	0.9900
CA_1—H7_1	0.9900	C_4—O_4	1.228 (2)
CA_1—H8_1	0.9900	C_4—N_5	1.339 (2)
C_1—O_1	1.235 (2)	N_5—CA_5	1.480 (2)
C_1—N_2	1.336 (2)	N_5—H1_5	0.8800
N_2—CA_2	1.465 (2)	CA_5—CB1_5	1.525 (2)
N_2—H1_2	0.8800	CA_5—CB3_5	1.528 (2)
CA_2—CB_2	1.530 (2)	CA_5—CB2_5	1.532 (2)
CA_2—C_2	1.538 (2)	CB1_5—H2_5	0.9800
CA_2—H2_2	1.0000	CB1_5—H3_5	0.9800
CB_2—SG_2	1.806 (1)	CB1_5—H4_5	0.9800
CB_2—H3_2	0.9900	CB2_5—H5_5	0.9800
CB_2—H4_2	0.9900	CB2_5—H6_5	0.9800
SG_2—CD_2	1.804 (2)	CB2_5—H7_5	0.9800
CD_2—H5_2	0.9800	CB3_5—H8_5	0.9800
CD_2—H6_2	0.9800	CB3_5—H9_5	0.9800
CD_2—H7_2	0.9800	CB3_5—H10_5	0.9800
C_2—O_2	1.228 (2)	O1_6—C1_6	1.215 (2)
C_2—N_3	1.342 (2)	C1_6—C3_6	1.495 (3)
N_3—CB1_3	1.459 (2)	C1_6—C2_6	1.501 (2)
N_3—H1_3	0.8800	C2_6—H1_6	0.9800
CB1_3—CG_3	1.538 (2)	C2_6—H2_6	0.9800
CB1_3—CA_3	1.548 (2)	C2_6—H3_6	0.9800
CB1_3—H2_3	1.0000	C3_6—H4_6	0.9800
CG_3—CD_3	1.508 (2)	C3_6—H5_6	0.9800
CG_3—H3_3	0.9900	C3_6—H6_6	0.9800
CG_3—H4_3	0.9900	C1_7—O1_7	1.204 (3)
CD_3—CE2_3	1.394 (2)	C1_7—C3_7	1.485 (3)
CD_3—CE1_3	1.396 (2)	C1_7—C2_7	1.487 (3)
CE1_3—CZ1_3	1.389 (2)	C2_7—H1_7	0.9800
CE1_3—H5_3	0.9500	C2_7—H2_7	0.9800
CZ1_3—CH_3	1.382 (2)	C2_7—H3_7	0.9800
CZ1_3—H6_3	0.9500	C3_7—H4_7	0.9800
CH_3—CZ2_3	1.384 (2)	C3_7—H5_7	0.9800
CH_3—H7_3	0.9500	C3_7—H6_7	0.9800
C8_1—N1_1—C2_1	117.0 (1)	CZ2_3—CE2_3—H9_3	119.7
N1_1—C2_1—C3_1	124.1 (2)	CD_3—CE2_3—H9_3	119.7
N1_1—C2_1—H1_1	117.9	OB2_3—CA_3—C_3	111.2 (1)
C3_1—C2_1—H1_1	117.9	OB2_3—CA_3—CB1_3	112.0 (1)
C2_1—C3_1—C9_1	119.1 (1)	C_3—CA_3—CB1_3	106.9 (1)
C2_1—C3_1—H2_1	120.5	OB2_3—CA_3—H10_3	108.9
C9_1—C3_1—H2_1	120.5	C_3—CA_3—H10_3	108.9
O11_1—C4_1—C5_1	125.6 (1)	CB1_3—CA_3—H10_3	108.9
O11_1—C4_1—C9_1	114.3 (1)	CA_3—OB2_3—H11_3	114.3
C5_1—C4_1—C9_1	120.1 (1)	O_3—C_3—N_4	122.2 (1)
C4_1—C5_1—C6_1	119.9 (1)	O_3—C_3—CA_3	120.0 (1)
C4_1—C5_1—H3_1	120.0	N_4—C_3—CA_3	117.5 (1)
C6_1—C5_1—H3_1	120.0	C_3—N_4—CD_4	126.0 (1)
C7_1—C6_1—C5_1	121.8 (1)	C_3—N_4—CA_4	119.1 (1)
C7_1—C6_1—H4_1	119.1	CD_4—N_4—CA_4	114.8 (1)
C5_1—C6_1—H4_1	119.1	N_4—CA_4—CB_4	106.7 (1)
C6_1—C7_1—C10_1	119.1 (1)	N_4—CA_4—C_4	109.0 (1)
C6_1—C7_1—H5_1	120.5	CB_4—CA_4—C_4	109.2 (1)
C10_1—C7_1—H5_1	120.5	N_4—CA_4—H1_4	110.6
N1_1—C8_1—C10_1	124.8 (1)	CB_4—CA_4—H1_4	110.6
N1_1—C8_1—H6_1	117.6	C_4—CA_4—H1_4	110.6
C10_1—C8_1—H6_1	117.6	CA_4—CB_4—SG_4	106.1 (1)
C10_1—C9_1—C3_1	118.0 (1)	CA_4—CB_4—H2_4	110.5
C10_1—C9_1—C4_1	118.7 (1)	SG_4—CB_4—H2_4	110.5
C3_1—C9_1—C4_1	123.3 (1)	CA_4—CB_4—H3_4	110.5
C7_1—C10_1—C9_1	120.5 (1)	SG_4—CB_4—H3_4	110.5
C7_1—C10_1—C8_1	122.5 (1)	H2_4—CB_4—H3_4	108.7
C9_1—C10_1—C8_1	117.0 (1)	CB_4—SG_4—CD_4	88.60 (7)
C4_1—O11_1—CA_1	117.7 (1)	N_4—CD_4—SG_4	103.87 (9)
O11_1—CA_1—C_1	115.1 (1)	N_4—CD_4—H4_4	111.0
O11_1—CA_1—H7_1	108.5	SG_4—CD_4—H4_4	111.0
C_1—CA_1—H7_1	108.5	N_4—CD_4—H5_4	111.0
O11_1—CA_1—H8_1	108.5	SG_4—CD_4—H5_4	111.0
C_1—CA_1—H8_1	108.5	H4_4—CD_4—H5_4	109.0
H7_1—CA_1—H8_1	107.5	O_4—C_4—N_5	125.8 (1)
O_1—C_1—N_2	124.5 (1)	O_4—C_4—CA_4	119.8 (1)
O_1—C_1—CA_1	117.7 (1)	N_5—C_4—CA_4	114.4 (1)
N_2—C_1—CA_1	117.8 (1)	C_4—N_5—CA_5	124.4 (1)
C_1—N_2—CA_2	121.9 (1)	C_4—N_5—H1_5	117.8
C_1—N_2—H1_2	119.1	CA_5—N_5—H1_5	117.8
CA_2—N_2—H1_2	119.1	N_5—CA_5—CB1_5	109.8 (1)
N_2—CA_2—CB_2	111.8 (1)	N_5—CA_5—CB3_5	109.5 (1)
N_2—CA_2—C_2	106.2 (1)	CB1_5—CA_5—CB3_5	111.4 (1)
CB_2—CA_2—C_2	109.7 (1)	N_5—CA_5—CB2_5	106.0 (1)
N_2—CA_2—H2_2	109.7	CB1_5—CA_5—CB2_5	109.4 (1)
CB_2—CA_2—H2_2	109.7	CB3_5—CA_5—CB2_5	110.7 (2)
C_2—CA_2—H2_2	109.7	CA_5—CB1_5—H2_5	109.5
CA_2—CB_2—SG_2	115.46 (9)	CA_5—CB1_5—H3_5	109.5
CA_2—CB_2—H3_2	108.4	H2_5—CB1_5—H3_5	109.5
SG_2—CB_2—H3_2	108.4	CA_5—CB1_5—H4_5	109.5
CA_2—CB_2—H4_2	108.4	H2_5—CB1_5—H4_5	109.5
SG_2—CB_2—H4_2	108.4	H3_5—CB1_5—H4_5	109.5
H3_2—CB_2—H4_2	107.5	CA_5—CB2_5—H5_5	109.5
CD_2—SG_2—CB_2	100.86 (7)	CA_5—CB2_5—H6_5	109.5
SG_2—CD_2—H5_2	109.5	H5_5—CB2_5—H6_5	109.5
SG_2—CD_2—H6_2	109.5	CA_5—CB2_5—H7_5	109.5
H5_2—CD_2—H6_2	109.5	H5_5—CB2_5—H7_5	109.5
SG_2—CD_2—H7_2	109.5	H6_5—CB2_5—H7_5	109.5
H5_2—CD_2—H7_2	109.5	CA_5—CB3_5—H8_5	109.5
H6_2—CD_2—H7_2	109.5	CA_5—CB3_5—H9_5	109.5
O_2—C_2—N_3	123.4 (1)	H8_5—CB3_5—H9_5	109.5
O_2—C_2—CA_2	121.2 (1)	CA_5—CB3_5—H10_5	109.5
N_3—C_2—CA_2	115.3 (1)	H8_5—CB3_5—H10_5	109.5
C_2—N_3—CB1_3	119.4 (1)	H9_5—CB3_5—H10_5	109.5
C_2—N_3—H1_3	120.3	O1_6—C1_6—C3_6	121.6 (2)
CB1_3—N_3—H1_3	120.3	O1_6—C1_6—C2_6	121.1 (2)
N_3—CB1_3—CG_3	111.1 (1)	C3_6—C1_6—C2_6	117.3 (2)
N_3—CB1_3—CA_3	110.6 (1)	C1_6—C2_6—H1_6	109.5
CG_3—CB1_3—CA_3	111.9 (1)	C1_6—C2_6—H2_6	109.5
N_3—CB1_3—H2_3	107.7	H1_6—C2_6—H2_6	109.5
CG_3—CB1_3—H2_3	107.7	C1_6—C2_6—H3_6	109.5
CA_3—CB1_3—H2_3	107.7	H1_6—C2_6—H3_6	109.5
CD_3—CG_3—CB1_3	113.3 (1)	H2_6—C2_6—H3_6	109.5
CD_3—CG_3—H3_3	108.9	C1_6—C3_6—H4_6	109.5
CB1_3—CG_3—H3_3	108.9	C1_6—C3_6—H5_6	109.5
CD_3—CG_3—H4_3	108.9	H4_6—C3_6—H5_6	109.5
CB1_3—CG_3—H4_3	108.9	C1_6—C3_6—H6_6	109.5
H3_3—CG_3—H4_3	107.7	H4_6—C3_6—H6_6	109.5
CE2_3—CD_3—CE1_3	118.5 (1)	H5_6—C3_6—H6_6	109.5
CE2_3—CD_3—CG_3	120.7 (1)	O1_7—C1_7—C3_7	122.3 (2)
CE1_3—CD_3—CG_3	120.7 (1)	O1_7—C1_7—C2_7	121.5 (2)
CZ1_3—CE1_3—CD_3	120.7 (1)	C3_7—C1_7—C2_7	116.2 (2)
CZ1_3—CE1_3—H5_3	119.7	C1_7—C2_7—H1_7	109.5
CD_3—CE1_3—H5_3	119.7	C1_7—C2_7—H2_7	109.5
CH_3—CZ1_3—CE1_3	120.2 (1)	H1_7—C2_7—H2_7	109.5
CH_3—CZ1_3—H6_3	119.9	C1_7—C2_7—H3_7	109.5
CE1_3—CZ1_3—H6_3	119.9	H1_7—C2_7—H3_7	109.5
CZ1_3—CH_3—CZ2_3	119.9 (1)	H2_7—C2_7—H3_7	109.5
CZ1_3—CH_3—H7_3	120.1	C1_7—C3_7—H4_7	109.5
CZ2_3—CH_3—H7_3	120.1	C1_7—C3_7—H5_7	109.5
CH_3—CZ2_3—CE2_3	120.0 (1)	H4_7—C3_7—H5_7	109.5
CH_3—CZ2_3—H8_3	120.0	C1_7—C3_7—H6_7	109.5
CE2_3—CZ2_3—H8_3	120.0	H4_7—C3_7—H6_7	109.5
CZ2_3—CE2_3—CD_3	120.6 (1)	H5_7—C3_7—H6_7	109.5
C8_1—N1_1—C2_1—C3_1	0.5 (2)	CA_3—CB1_3—CG_3—CD_3	−168.5 (1)
N1_1—C2_1—C3_1—C9_1	−0.4 (2)	CB1_3—CG_3—CD_3—CE2_3	133.3 (1)
O11_1—C4_1—C5_1—C6_1	−178.2 (1)	CB1_3—CG_3—CD_3—CE1_3	−44.1 (2)
C9_1—C4_1—C5_1—C6_1	0.3 (2)	CE2_3—CD_3—CE1_3—CZ1_3	−1.4 (2)
C4_1—C5_1—C6_1—C7_1	0.6 (2)	CG_3—CD_3—CE1_3—CZ1_3	176.1 (1)
C5_1—C6_1—C7_1—C10_1	−0.7 (2)	CD_3—CE1_3—CZ1_3—CH_3	0.0 (2)
C2_1—N1_1—C8_1—C10_1	−0.5 (2)	CE1_3—CZ1_3—CH_3—CZ2_3	1.3 (2)
C2_1—C3_1—C9_1—C10_1	0.1 (2)	CZ1_3—CH_3—CZ2_3—CE2_3	−1.2 (2)
C2_1—C3_1—C9_1—C4_1	178.9 (1)	CH_3—CZ2_3—CE2_3—CD_3	−0.2 (2)
O11_1—C4_1—C9_1—C10_1	177.6 (1)	CE1_3—CD_3—CE2_3—CZ2_3	1.5 (2)
C5_1—C4_1—C9_1—C10_1	−1.0 (2)	CG_3—CD_3—CE2_3—CZ2_3	−176.0 (1)
O11_1—C4_1—C9_1—C3_1	−1.2 (2)	N_3—CB1_3—CA_3—OB2_3	−67.2 (1)
C5_1—C4_1—C9_1—C3_1	−179.8 (1)	CG_3—CB1_3—CA_3—OB2_3	57.3 (1)
C6_1—C7_1—C10_1—C9_1	−0.1 (2)	N_3—CB1_3—CA_3—C_3	170.8 (1)
C6_1—C7_1—C10_1—C8_1	179.7 (1)	CG_3—CB1_3—CA_3—C_3	−64.8 (1)
C3_1—C9_1—C10_1—C7_1	179.8 (1)	OB2_3—CA_3—C_3—O_3	−24.1 (2)
C4_1—C9_1—C10_1—C7_1	1.0 (2)	CB1_3—CA_3—C_3—O_3	98.5 (1)
C3_1—C9_1—C10_1—C8_1	−0.1 (2)	OB2_3—CA_3—C_3—N_4	162.2 (1)
C4_1—C9_1—C10_1—C8_1	−178.9 (1)	CB1_3—CA_3—C_3—N_4	−75.3 (1)
N1_1—C8_1—C10_1—C7_1	−179.6 (2)	O_3—C_3—N_4—CD_4	174.7 (1)
N1_1—C8_1—C10_1—C9_1	0.3 (2)	CA_3—C_3—N_4—CD_4	−11.8 (2)
C5_1—C4_1—O11_1—CA_1	−8.9 (2)	O_3—C_3—N_4—CA_4	−8.9 (2)
C9_1—C4_1—O11_1—CA_1	172.6 (1)	CA_3—C_3—N_4—CA_4	164.7 (1)
C4_1—O11_1—CA_1—C_1	79.7 (1)	C_3—N_4—CA_4—CB_4	−179.4 (1)
O11_1—CA_1—C_1—O_1	−177.4 (1)	CD_4—N_4—CA_4—CB_4	−2.5 (2)
O11_1—CA_1—C_1—N_2	2.3 (2)	C_3—N_4—CA_4—C_4	−61.5 (2)
O_1—C_1—N_2—CA_2	3.0 (2)	CD_4—N_4—CA_4—C_4	115.3 (1)
CA_1—C_1—N_2—CA_2	−176.7 (1)	N_4—CA_4—CB_4—SG_4	−27.3 (1)
C_1—N_2—CA_2—CB_2	98.9 (1)	C_4—CA_4—CB_4—SG_4	−145.04 (9)
C_1—N_2—CA_2—C_2	−141.5 (1)	CA_4—CB_4—SG_4—CD_4	39.1 (1)
N_2—CA_2—CB_2—SG_2	−59.3 (1)	C_3—N_4—CD_4—SG_4	−152.6 (1)
C_2—CA_2—CB_2—SG_2	−176.79 (9)	CA_4—N_4—CD_4—SG_4	30.8 (1)
CA_2—CB_2—SG_2—CD_2	−67.3 (1)	CB_4—SG_4—CD_4—N_4	−39.4 (1)
N_2—CA_2—C_2—O_2	−92.7 (1)	N_4—CA_4—C_4—O_4	−41.9 (2)
CB_2—CA_2—C_2—O_2	28.3 (2)	CB_4—CA_4—C_4—O_4	74.4 (2)
N_2—CA_2—C_2—N_3	83.1 (1)	N_4—CA_4—C_4—N_5	140.0 (1)
CB_2—CA_2—C_2—N_3	−155.9 (1)	CB_4—CA_4—C_4—N_5	−103.8 (1)
O_2—C_2—N_3—CB1_3	16.2 (2)	O_4—C_4—N_5—CA_5	1.5 (2)
CA_2—C_2—N_3—CB1_3	−159.5 (1)	CA_4—C_4—N_5—CA_5	179.6 (1)
C_2—N_3—CB1_3—CG_3	153.5 (1)	C_4—N_5—CA_5—CB1_5	57.0 (2)
C_2—N_3—CB1_3—CA_3	−81.6 (1)	C_4—N_5—CA_5—CB3_5	−65.6 (2)
N_3—CB1_3—CG_3—CD_3	−44.3 (2)	C_4—N_5—CA_5—CB2_5	175.0 (1)