Turn-over of an oxazoline ring induced by chiral change of a folded ascidiacycl­amide analogue: cyclo(Ile-D-aThr-D-Val-Thz-Ile-D-Oxz-D-Val-Thz) N,N-di­methyl­form­amide disolvate

Ascidiacycl­amide (ASC) has two oxazoline (Oxz) residues with 2S,3R configurations. In the title compound, C₃₆H₅₄N₈O₇S₂·2C₃H₇NO, these Oxz residues were replaced with D-aThr and (2R,3S)-Oxz (D-Oxz). The overall structure is similar to the folded from of ASC analogues previously reported, but a difference was found at the D-Oxz residue. The D-Oxz ring was turned over in relation to the disposition of the Oxz rings in natural ASC. This result suggested that the modification of Oxz could induce a new type of molecular folding in ASC.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.148
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.41 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors  for      C1_10
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for      N1_10
PLAT322_ALERT_2_C Check Hybridisation of  SG_8   in Main Residue .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........        131
PLAT751_ALERT_4_C Bond    Calc     0.84092, Rep    0.841(2) ......  Senseless su
              OG1_2-H4_2    1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      109.40, Rep    109.4(2) ......  Senseless su
              CB_2 -OG1_2-H4_2    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C3 H7 N O

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           27.10
           From the CIF: _reflns_number_total              10109
           Count of symmetry unique reflns         5610
           Completeness (_total/calc)            180.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      4499
           Fraction of Friedel pairs measured     0.802
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

ascidiacyclamide analogue No.9 cyclo(Ile-D-aThr(3R)-D-Val-Thz-Ile-D-Oxz(3S)-D-Val-Thz)isoleucyl-D-

Crystal data

C36H54N8O7S2·2C3H7NO	F(000) = 988
Mr = 921.18	Dx = 1.265 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 13.031 (1) Å	Cell parameters from 8060 reflections
b = 11.0503 (9) Å	θ = 2.5–28.1°
c = 17.358 (1) Å	µ = 0.17 mm^−1
β = 104.654 (1)°	T = 120 K
V = 2418.2 (3) Å^3	Plate, colourless
Z = 2	0.40 × 0.30 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	10109 independent reflections
Radiation source: MacScience, M18XCE rotating anode	8732 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.366 pixels mm^-1	θmax = 27.1°, θmin = 2.4°
ω scans	h = −16→16
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.887, Tmax = 0.997	l = −22→22
20955 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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.6439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.013
10109 reflections	Δρmax = 0.80 e Å^−3
582 parameters	Δρmin = −0.52 e Å^−3
1 restraint	Absolute structure: Flack (1983), 4576 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (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
N_1	−0.08514 (18)	0.6637 (2)	0.72573 (12)	0.0251 (4)
H1_1	−0.1179	0.6981	0.7585	0.030*
CA_1	−0.1448 (2)	0.6325 (2)	0.64546 (15)	0.0270 (5)
H2_1	−0.1220	0.5502	0.6324	0.032*
CB_1	−0.2639 (2)	0.6282 (3)	0.64152 (17)	0.0316 (6)
H3_1	−0.2857	0.7099	0.6563	0.038*
CG2_1	−0.3260 (3)	0.6010 (5)	0.5565 (2)	0.0582 (10)
H4_1	−0.3119	0.5177	0.5428	0.087*
H5_1	−0.3040	0.6570	0.5199	0.087*
H6_1	−0.4020	0.6110	0.5520	0.087*
CG1_1	−0.2860 (3)	0.5362 (3)	0.7015 (2)	0.0441 (8)
H7_1	−0.2676	0.4543	0.6861	0.053*
H8_1	−0.2394	0.5543	0.7547	0.053*
CD_1	−0.4007 (3)	0.5360 (5)	0.7069 (3)	0.0662 (12)
H9_1	−0.4196	0.6168	0.7220	0.099*
H10_1	−0.4090	0.4771	0.7471	0.099*
H11_1	−0.4472	0.5138	0.6551	0.099*
C_1	−0.1184 (2)	0.7232 (2)	0.58692 (14)	0.0243 (5)
O_1	−0.14067 (15)	0.83275 (17)	0.58810 (11)	0.0271 (4)
N_2	−0.06728 (18)	0.6767 (2)	0.53570 (13)	0.0264 (5)
H1_2	−0.0586	0.5978	0.5350	0.032*
CA_2	−0.0256 (2)	0.7500 (3)	0.48147 (14)	0.0268 (5)
H2_2	−0.0834	0.8054	0.4529	0.032*
CB_2	0.0021 (2)	0.6648 (3)	0.41898 (16)	0.0338 (6)
H3_2	−0.0629	0.6181	0.3923	0.041*
OG1_2	0.07956 (19)	0.5827 (2)	0.46081 (13)	0.0398 (5)
H4_2	0.0829	0.5230	0.4315	0.060*
CG2_2	0.0408 (3)	0.7327 (3)	0.35591 (18)	0.0439 (8)
H5_2	0.1068	0.7752	0.3809	0.066*
H6_2	−0.0131	0.7914	0.3297	0.066*
H7_2	0.0537	0.6753	0.3163	0.066*
C_2	0.0688 (2)	0.8285 (2)	0.52398 (15)	0.0260 (5)
O_2	0.09453 (19)	0.91614 (18)	0.48951 (12)	0.0374 (5)
N_3	0.11981 (17)	0.7952 (2)	0.59810 (12)	0.0250 (4)
H1_3	0.1043	0.7254	0.6168	0.030*
CA_3	0.2004 (2)	0.8722 (2)	0.64836 (15)	0.0258 (5)
H2_3	0.2050	0.9468	0.6168	0.031*
CB_3	0.3114 (2)	0.8145 (3)	0.66896 (17)	0.0314 (6)
H3_3	0.3626	0.8747	0.7003	0.038*
CG1_3	0.3433 (3)	0.7891 (3)	0.59174 (19)	0.0400 (7)
H4_3	0.4148	0.7544	0.6042	0.060*
H5_3	0.3423	0.8648	0.5622	0.060*
H6_3	0.2931	0.7317	0.5593	0.060*
CG2_3	0.3186 (2)	0.6994 (3)	0.7187 (2)	0.0388 (7)
H7_3	0.2656	0.6410	0.6907	0.058*
H8_3	0.3052	0.7191	0.7704	0.058*
H9_3	0.3897	0.6643	0.7271	0.058*
C3_4	0.1609 (2)	0.9120 (2)	0.71957 (15)	0.0266 (5)
N_4	0.06069 (17)	0.9225 (2)	0.71768 (13)	0.0248 (4)
CA_4	0.0480 (2)	0.9632 (2)	0.78972 (15)	0.0250 (5)
CB_4	0.1392 (2)	0.9845 (3)	0.84708 (17)	0.0324 (6)
H1_4	0.1429	1.0127	0.8994	0.039*
SG_4	0.24549 (5)	0.95265 (8)	0.81022 (4)	0.03797 (19)
C_4	−0.0591 (2)	0.9849 (2)	0.80230 (15)	0.0248 (5)
O_4	−0.07135 (16)	1.01788 (18)	0.86714 (11)	0.0307 (4)
N_5	−0.14170 (17)	0.9694 (2)	0.73819 (12)	0.0238 (4)
H1_5	−0.1316	0.9423	0.6930	0.029*
CA_5	−0.2478 (2)	0.9985 (3)	0.74531 (16)	0.0268 (5)
H2_5	−0.2473	1.0846	0.7632	0.032*
CB_5	−0.3306 (2)	0.9878 (3)	0.66426 (16)	0.0295 (6)
H3_5	−0.3193	0.9075	0.6410	0.035*
CG2_5	−0.4433 (3)	0.9890 (4)	0.6739 (2)	0.0487 (9)
H4_5	−0.4566	0.9141	0.7000	0.073*
H5_5	−0.4934	0.9950	0.6214	0.073*
H6_5	−0.4525	1.0586	0.7064	0.073*
CG1_5	−0.3150 (3)	1.0854 (3)	0.60519 (17)	0.0354 (6)
H7_5	−0.2412	1.0805	0.6000	0.043*
H8_5	−0.3627	1.0672	0.5523	0.043*
CD_5	−0.3360 (4)	1.2139 (4)	0.6279 (3)	0.0639 (11)
H9_5	−0.4082	1.2196	0.6348	0.096*
H10_5	−0.3284	1.2695	0.5857	0.096*
H11_5	−0.2850	1.2357	0.6779	0.096*
C3_6	−0.2761 (2)	0.9204 (3)	0.80791 (15)	0.0289 (6)
N_6	−0.25738 (19)	0.8090 (2)	0.81808 (14)	0.0313 (5)
CA_6	−0.2979 (3)	0.7740 (3)	0.88755 (17)	0.0369 (7)
H1_6	−0.3513	0.7078	0.8711	0.044*
CB_6	−0.3550 (2)	0.8889 (3)	0.90733 (18)	0.0385 (7)
H2_6	−0.3265	0.9119	0.9645	0.046*
OG1_6	−0.32735 (17)	0.9799 (2)	0.85562 (12)	0.0372 (5)
CG2_6	−0.4748 (3)	0.8767 (5)	0.8877 (2)	0.0550 (10)
H3_6	−0.5061	0.9541	0.8973	0.082*
H4_6	−0.4940	0.8141	0.9216	0.082*
H5_6	−0.5016	0.8540	0.8317	0.082*
C_6	−0.2089 (2)	0.7295 (3)	0.95765 (18)	0.0395 (7)
O_6	−0.2255 (2)	0.6410 (3)	0.99588 (18)	0.0651 (8)
N_7	−0.1186 (2)	0.7923 (2)	0.97374 (13)	0.0324 (5)
H1_7	−0.1189	0.8679	0.9578	0.039*
CA_7	−0.0189 (2)	0.7370 (3)	1.01763 (15)	0.0323 (6)
H2_7	−0.0376	0.6596	1.0406	0.039*
CB_7	0.0449 (3)	0.8121 (3)	1.08695 (18)	0.0431 (7)
H3_7	0.1085	0.7633	1.1140	0.052*
CG1_7	0.0842 (3)	0.9283 (3)	1.0602 (2)	0.0516 (9)
H4_7	0.1347	0.9105	1.0284	0.077*
H5_7	0.1195	0.9763	1.1069	0.077*
H6_7	0.0242	0.9741	1.0279	0.077*
CG2_7	−0.0218 (4)	0.8319 (3)	1.14758 (18)	0.0518 (9)
H7_7	0.0217	0.8714	1.1952	0.078*
H8_7	−0.0467	0.7536	1.1623	0.078*
H9_7	−0.0830	0.8831	1.1238	0.078*
C3_8	0.0414 (2)	0.7032 (3)	0.95656 (16)	0.0300 (6)
N_8	−0.00359 (19)	0.7027 (2)	0.88117 (13)	0.0283 (5)
CA_8	0.0642 (2)	0.6596 (3)	0.83763 (16)	0.0281 (5)
CB_8	0.1628 (2)	0.6300 (3)	0.88046 (16)	0.0323 (6)
H1_8	0.2183	0.6010	0.8589	0.039*
SG_8	0.17221 (6)	0.65314 (7)	0.97993 (4)	0.03790 (18)
C_8	0.0192 (2)	0.6409 (2)	0.75048 (15)	0.0270 (5)
O_8	0.07286 (16)	0.60245 (19)	0.70702 (12)	0.0329 (4)
O1_9	0.3277 (4)	0.1383 (4)	0.6913 (4)	0.1277 (19)
C1_9	0.3352 (6)	0.2216 (6)	0.6494 (3)	0.0939 (17)
H1_9	0.3763	0.2085	0.6121	0.113*
N1_9	0.2923 (3)	0.3306 (3)	0.6491 (3)	0.0785 (13)
C2_9	0.2373 (4)	0.3755 (5)	0.7067 (3)	0.0804 (14)
H2_9	0.2115	0.3069	0.7323	0.121*
H3_9	0.1771	0.4258	0.6795	0.121*
H4_9	0.2863	0.4238	0.7472	0.121*
C3_9	0.3085 (6)	0.4176 (6)	0.5901 (3)	0.0957 (18)
H5_9	0.3388	0.3763	0.5511	0.144*
H6_9	0.3572	0.4812	0.6167	0.144*
H7_9	0.2403	0.4539	0.5630	0.144*
O1_10	−0.4012 (3)	1.0178 (4)	1.0817 (2)	0.0960 (13)
C1_10	−0.4798 (6)	0.9642 (10)	1.0847 (4)	0.127 (3)
H1_10	−0.5419	1.0114	1.0805	0.152*
N1_10	−0.4898 (4)	0.8426 (6)	1.0936 (3)	0.0917 (17)
C2_10	−0.3894 (9)	0.7665 (10)	1.1036 (4)	0.145 (4)
H2_10	−0.3298	0.8192	1.1012	0.218*
H3_10	−0.4001	0.7063	1.0609	0.218*
H4_10	−0.3738	0.7253	1.1553	0.218*
C3_10	−0.5811 (10)	0.7901 (14)	1.0966 (8)	0.249 (9)
H5_10	−0.5772	0.7649	1.1514	0.373*
H6_10	−0.5935	0.7192	1.0616	0.373*
H7_10	−0.6394	0.8478	1.0790	0.373*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N_1	0.0298 (11)	0.0258 (11)	0.0216 (10)	0.0003 (9)	0.0099 (9)	0.0002 (9)
CA_1	0.0285 (13)	0.0272 (13)	0.0253 (12)	0.0015 (10)	0.0068 (11)	−0.0032 (10)
CB_1	0.0267 (13)	0.0315 (15)	0.0373 (14)	0.0006 (10)	0.0094 (12)	−0.0030 (11)
CG2_1	0.0373 (19)	0.085 (3)	0.0463 (19)	−0.0159 (19)	0.0005 (16)	−0.010 (2)
CG1_1	0.0392 (17)	0.0337 (16)	0.064 (2)	−0.0031 (13)	0.0220 (16)	0.0017 (15)
CD_1	0.046 (2)	0.086 (3)	0.071 (3)	−0.019 (2)	0.023 (2)	0.002 (2)
C_1	0.0259 (12)	0.0275 (13)	0.0188 (11)	0.0010 (10)	0.0041 (10)	−0.0035 (10)
O_1	0.0307 (10)	0.0270 (9)	0.0245 (8)	0.0036 (7)	0.0089 (7)	−0.0013 (7)
N_2	0.0307 (11)	0.0255 (11)	0.0242 (10)	0.0012 (9)	0.0092 (9)	−0.0046 (9)
CA_2	0.0299 (13)	0.0311 (14)	0.0200 (11)	0.0054 (10)	0.0073 (10)	−0.0006 (10)
CB_2	0.0399 (15)	0.0372 (15)	0.0251 (12)	−0.0032 (12)	0.0097 (11)	−0.0096 (12)
OG1_2	0.0503 (13)	0.0327 (11)	0.0422 (12)	0.0067 (10)	0.0222 (10)	−0.0038 (9)
CG2_2	0.059 (2)	0.0483 (19)	0.0299 (14)	0.0030 (16)	0.0208 (14)	−0.0043 (13)
C_2	0.0350 (14)	0.0241 (12)	0.0206 (11)	0.0035 (11)	0.0101 (10)	−0.0018 (10)
O_2	0.0567 (13)	0.0265 (10)	0.0284 (9)	−0.0017 (9)	0.0095 (9)	0.0059 (8)
N_3	0.0274 (11)	0.0256 (11)	0.0227 (10)	−0.0011 (9)	0.0077 (9)	−0.0008 (9)
CA_3	0.0245 (13)	0.0279 (13)	0.0263 (12)	0.0004 (10)	0.0086 (10)	−0.0012 (10)
CB_3	0.0250 (13)	0.0360 (15)	0.0341 (14)	0.0011 (11)	0.0088 (11)	−0.0024 (12)
CG1_3	0.0325 (15)	0.0521 (19)	0.0395 (16)	0.0062 (14)	0.0165 (13)	−0.0025 (14)
CG2_3	0.0321 (15)	0.0382 (16)	0.0463 (17)	0.0070 (12)	0.0107 (13)	0.0019 (14)
C3_4	0.0251 (13)	0.0295 (13)	0.0238 (12)	−0.0009 (10)	0.0038 (10)	−0.0018 (10)
N_4	0.0241 (11)	0.0254 (11)	0.0247 (10)	−0.0007 (8)	0.0057 (8)	−0.0009 (9)
CA_4	0.0274 (12)	0.0234 (12)	0.0238 (11)	−0.0006 (10)	0.0054 (10)	−0.0007 (10)
CB_4	0.0283 (14)	0.0385 (16)	0.0289 (13)	0.0023 (11)	0.0045 (11)	−0.0094 (12)
SG_4	0.0221 (3)	0.0576 (5)	0.0318 (3)	0.0019 (3)	0.0022 (3)	−0.0138 (3)
C_4	0.0279 (13)	0.0212 (12)	0.0260 (12)	−0.0003 (10)	0.0081 (10)	−0.0013 (10)
O_4	0.0348 (11)	0.0321 (10)	0.0263 (9)	−0.0009 (8)	0.0099 (8)	−0.0081 (8)
N_5	0.0250 (10)	0.0247 (11)	0.0232 (9)	0.0000 (8)	0.0091 (8)	−0.0015 (9)
CA_5	0.0251 (13)	0.0262 (12)	0.0307 (13)	0.0018 (10)	0.0103 (11)	0.0002 (10)
CB_5	0.0284 (13)	0.0297 (14)	0.0292 (13)	0.0032 (11)	0.0051 (11)	0.0035 (11)
CG2_5	0.0282 (15)	0.069 (2)	0.0458 (17)	−0.0004 (15)	0.0043 (13)	0.0178 (17)
CG1_5	0.0369 (16)	0.0377 (16)	0.0320 (14)	0.0011 (12)	0.0094 (12)	0.0055 (12)
CD_5	0.103 (3)	0.0357 (19)	0.059 (2)	0.010 (2)	0.031 (2)	0.0129 (17)
C3_6	0.0243 (13)	0.0365 (15)	0.0264 (12)	0.0018 (11)	0.0076 (10)	0.0010 (11)
N_6	0.0333 (12)	0.0325 (13)	0.0293 (11)	−0.0001 (10)	0.0099 (10)	0.0046 (10)
CA_6	0.0344 (15)	0.0454 (17)	0.0307 (14)	−0.0003 (13)	0.0080 (12)	0.0112 (13)
CB_6	0.0325 (15)	0.056 (2)	0.0288 (14)	0.0029 (14)	0.0109 (12)	0.0046 (13)
OG1_6	0.0374 (11)	0.0438 (12)	0.0358 (10)	0.0081 (9)	0.0191 (9)	0.0015 (9)
CG2_6	0.0341 (18)	0.086 (3)	0.0470 (19)	−0.0014 (18)	0.0145 (15)	0.0079 (19)
C_6	0.0380 (16)	0.0481 (19)	0.0353 (15)	0.0059 (14)	0.0148 (13)	0.0152 (14)
O_6	0.0484 (15)	0.077 (2)	0.0701 (17)	−0.0012 (13)	0.0151 (13)	0.0487 (16)
N_7	0.0420 (14)	0.0327 (12)	0.0226 (10)	0.0072 (10)	0.0086 (10)	0.0028 (9)
CA_7	0.0391 (15)	0.0359 (16)	0.0202 (12)	0.0027 (12)	0.0044 (11)	0.0039 (11)
CB_7	0.057 (2)	0.0439 (18)	0.0256 (14)	0.0016 (15)	0.0045 (13)	−0.0010 (13)
CG1_7	0.067 (2)	0.0405 (18)	0.0422 (17)	−0.0022 (16)	0.0044 (17)	−0.0008 (15)
CG2_7	0.088 (3)	0.0424 (19)	0.0259 (15)	0.0038 (18)	0.0162 (16)	−0.0032 (14)
C3_8	0.0331 (14)	0.0295 (13)	0.0255 (13)	0.0025 (11)	0.0042 (11)	0.0032 (11)
N_8	0.0341 (12)	0.0258 (11)	0.0242 (10)	0.0006 (9)	0.0063 (9)	0.0025 (9)
CA_8	0.0342 (14)	0.0244 (12)	0.0268 (12)	−0.0006 (11)	0.0097 (11)	0.0049 (11)
CB_8	0.0320 (14)	0.0372 (16)	0.0266 (13)	−0.0006 (11)	0.0055 (11)	0.0023 (11)
SG_8	0.0335 (4)	0.0473 (4)	0.0287 (3)	0.0039 (3)	0.0002 (3)	0.0027 (3)
C_8	0.0304 (13)	0.0261 (13)	0.0262 (12)	−0.0011 (10)	0.0104 (10)	0.0047 (10)
O_8	0.0323 (11)	0.0366 (11)	0.0321 (10)	0.0050 (8)	0.0122 (8)	0.0017 (9)
O1_9	0.128 (4)	0.075 (3)	0.196 (5)	0.018 (3)	0.071 (4)	0.063 (3)
C1_9	0.131 (5)	0.074 (4)	0.076 (3)	0.014 (4)	0.025 (3)	0.001 (3)
N1_9	0.075 (3)	0.050 (2)	0.085 (3)	0.0186 (18)	−0.028 (2)	−0.026 (2)
C2_9	0.080 (3)	0.065 (3)	0.096 (4)	−0.013 (3)	0.024 (3)	−0.004 (3)
C3_9	0.117 (5)	0.091 (4)	0.069 (3)	−0.026 (4)	0.004 (3)	−0.013 (3)
O1_10	0.072 (2)	0.126 (3)	0.095 (3)	−0.041 (2)	0.030 (2)	−0.031 (2)
C1_10	0.083 (4)	0.216 (11)	0.091 (4)	−0.033 (5)	0.039 (3)	−0.066 (6)
N1_10	0.094 (3)	0.117 (4)	0.069 (3)	−0.056 (3)	0.029 (2)	−0.025 (3)
C2_10	0.209 (10)	0.150 (8)	0.075 (4)	−0.022 (8)	0.033 (5)	0.014 (5)
C3_10	0.186 (11)	0.33 (2)	0.280 (16)	−0.177 (13)	0.145 (11)	−0.148 (15)

Geometric parameters (Å, º)

N_1—C_8	1.342 (4)	CG2_5—H5_5	0.9800
N_1—CA_1	1.455 (3)	CG2_5—H6_5	0.9800
N_1—H1_1	0.8800	CG1_5—CD_5	1.517 (5)
CA_1—C_1	1.527 (4)	CG1_5—H7_5	0.9900
CA_1—CB_1	1.536 (4)	CG1_5—H8_5	0.9900
CA_1—H2_1	1.0000	CD_5—H9_5	0.9800
CB_1—CG2_1	1.523 (5)	CD_5—H10_5	0.9800
CB_1—CG1_1	1.533 (5)	CD_5—H11_5	0.9800
CB_1—H3_1	1.0000	C3_6—N_6	1.258 (4)
CG2_1—H4_1	0.9800	C3_6—OG1_6	1.358 (3)
CG2_1—H5_1	0.9800	N_6—CA_6	1.485 (4)
CG2_1—H6_1	0.9800	CA_6—C_6	1.534 (4)
CG1_1—CD_1	1.521 (5)	CA_6—CB_6	1.553 (5)
CG1_1—H7_1	0.9900	CA_6—H1_6	1.0000
CG1_1—H8_1	0.9900	CB_6—OG1_6	1.453 (4)
CD_1—H9_1	0.9800	CB_6—CG2_6	1.517 (5)
CD_1—H10_1	0.9800	CB_6—H2_6	1.0000
CD_1—H11_1	0.9800	CG2_6—H3_6	0.9800
C_1—O_1	1.246 (3)	CG2_6—H4_6	0.9800
C_1—N_2	1.341 (3)	CG2_6—H5_6	0.9800
N_2—CA_2	1.448 (3)	C_6—O_6	1.231 (4)
N_2—H1_2	0.8800	C_6—N_7	1.334 (4)
CA_2—C_2	1.533 (4)	N_7—CA_7	1.463 (4)
CA_2—CB_2	1.547 (4)	N_7—H1_7	0.8800
CA_2—H2_2	1.0000	CA_7—C3_8	1.517 (4)
CB_2—OG1_2	1.413 (4)	CA_7—CB_7	1.523 (4)
CB_2—CG2_2	1.515 (4)	CA_7—H2_7	1.0000
CB_2—H3_2	1.0000	CB_7—CG1_7	1.499 (5)
OG1_2—H4_2	0.841 (2)	CB_7—CG2_7	1.541 (5)
CG2_2—H5_2	0.9800	CB_7—H3_7	1.0000
CG2_2—H6_2	0.9800	CG1_7—H4_7	0.9800
CG2_2—H7_2	0.9800	CG1_7—H5_7	0.9800
C_2—O_2	1.229 (3)	CG1_7—H6_7	0.9800
C_2—N_3	1.342 (3)	CG2_7—H7_7	0.9800
N_3—CA_3	1.457 (3)	CG2_7—H8_7	0.9800
N_3—H1_3	0.8800	CG2_7—H9_7	0.9800
CA_3—C3_4	1.520 (4)	C3_8—N_8	1.292 (3)
CA_3—CB_3	1.538 (4)	C3_8—SG_8	1.740 (3)
CA_3—H2_3	1.0000	N_8—CA_8	1.384 (4)
CB_3—CG1_3	1.526 (4)	CA_8—CB_8	1.352 (4)
CB_3—CG2_3	1.526 (4)	CA_8—C_8	1.492 (4)
CB_3—H3_3	1.0000	CB_8—SG_8	1.719 (3)
CG1_3—H4_3	0.9800	CB_8—H1_8	0.9500
CG1_3—H5_3	0.9800	C_8—O_8	1.227 (3)
CG1_3—H6_3	0.9800	O1_9—C1_9	1.193 (7)
CG2_3—H7_3	0.9800	C1_9—N1_9	1.327 (7)
CG2_3—H8_3	0.9800	C1_9—H1_9	0.9500
CG2_3—H9_3	0.9800	N1_9—C2_9	1.457 (7)
C3_4—N_4	1.303 (3)	N1_9—C3_9	1.458 (8)
C3_4—SG_4	1.736 (3)	C2_9—H2_9	0.9800
N_4—CA_4	1.378 (3)	C2_9—H3_9	0.9800
CA_4—CB_4	1.364 (4)	C2_9—H4_9	0.9800
CA_4—C_4	1.486 (4)	C3_9—H5_9	0.9800
CB_4—SG_4	1.703 (3)	C3_9—H6_9	0.9800
CB_4—H1_4	0.9500	C3_9—H7_9	0.9800
C_4—O_4	1.231 (3)	O1_10—C1_10	1.196 (8)
C_4—N_5	1.349 (3)	C1_10—N1_10	1.362 (12)
N_5—CA_5	1.455 (3)	C1_10—H1_10	0.9500
N_5—H1_5	0.8800	N1_10—C3_10	1.336 (9)
CA_5—C3_6	1.505 (4)	N1_10—C2_10	1.527 (12)
CA_5—CB_5	1.545 (4)	C2_10—H2_10	0.9800
CA_5—H2_5	1.0000	C2_10—H3_10	0.9800
CB_5—CG2_5	1.520 (4)	C2_10—H4_10	0.9800
CB_5—CG1_5	1.536 (4)	C3_10—H5_10	0.9800
CB_5—H3_5	1.0000	C3_10—H6_10	0.9800
CG2_5—H4_5	0.9800	C3_10—H7_10	0.9800
C_8—N_1—CA_1	121.0 (2)	H4_5—CG2_5—H5_5	109.5
C_8—N_1—H1_1	119.5	CB_5—CG2_5—H6_5	109.5
CA_1—N_1—H1_1	119.5	H4_5—CG2_5—H6_5	109.5
N_1—CA_1—C_1	109.0 (2)	H5_5—CG2_5—H6_5	109.5
N_1—CA_1—CB_1	109.8 (2)	CD_5—CG1_5—CB_5	114.9 (3)
C_1—CA_1—CB_1	112.7 (2)	CD_5—CG1_5—H7_5	108.5
N_1—CA_1—H2_1	108.4	CB_5—CG1_5—H7_5	108.5
C_1—CA_1—H2_1	108.4	CD_5—CG1_5—H8_5	108.5
CB_1—CA_1—H2_1	108.4	CB_5—CG1_5—H8_5	108.5
CG2_1—CB_1—CG1_1	112.5 (3)	H7_5—CG1_5—H8_5	107.5
CG2_1—CB_1—CA_1	109.4 (2)	CG1_5—CD_5—H9_5	109.5
CG1_1—CB_1—CA_1	110.6 (2)	CG1_5—CD_5—H10_5	109.5
CG2_1—CB_1—H3_1	108.1	H9_5—CD_5—H10_5	109.5
CG1_1—CB_1—H3_1	108.1	CG1_5—CD_5—H11_5	109.5
CA_1—CB_1—H3_1	108.1	H9_5—CD_5—H11_5	109.5
CB_1—CG2_1—H4_1	109.5	H10_5—CD_5—H11_5	109.5
CB_1—CG2_1—H5_1	109.5	N_6—C3_6—OG1_6	119.7 (3)
H4_1—CG2_1—H5_1	109.5	N_6—C3_6—CA_5	126.0 (3)
CB_1—CG2_1—H6_1	109.5	OG1_6—C3_6—CA_5	114.2 (2)
H4_1—CG2_1—H6_1	109.5	C3_6—N_6—CA_6	105.8 (2)
H5_1—CG2_1—H6_1	109.5	N_6—CA_6—C_6	112.0 (2)
CD_1—CG1_1—CB_1	113.5 (3)	N_6—CA_6—CB_6	104.8 (2)
CD_1—CG1_1—H7_1	108.9	C_6—CA_6—CB_6	113.3 (3)
CB_1—CG1_1—H7_1	108.9	N_6—CA_6—H1_6	108.9
CD_1—CG1_1—H8_1	108.9	C_6—CA_6—H1_6	108.9
CB_1—CG1_1—H8_1	108.9	CB_6—CA_6—H1_6	108.9
H7_1—CG1_1—H8_1	107.7	OG1_6—CB_6—CG2_6	109.0 (3)
CG1_1—CD_1—H9_1	109.5	OG1_6—CB_6—CA_6	102.8 (2)
CG1_1—CD_1—H10_1	109.5	CG2_6—CB_6—CA_6	113.6 (3)
H9_1—CD_1—H10_1	109.5	OG1_6—CB_6—H2_6	110.4
CG1_1—CD_1—H11_1	109.5	CG2_6—CB_6—H2_6	110.4
H9_1—CD_1—H11_1	109.5	CA_6—CB_6—H2_6	110.4
H10_1—CD_1—H11_1	109.5	C3_6—OG1_6—CB_6	106.2 (2)
O_1—C_1—N_2	122.7 (2)	CB_6—CG2_6—H3_6	109.5
O_1—C_1—CA_1	122.3 (2)	CB_6—CG2_6—H4_6	109.5
N_2—C_1—CA_1	115.0 (2)	H3_6—CG2_6—H4_6	109.5
C_1—N_2—CA_2	123.2 (2)	CB_6—CG2_6—H5_6	109.5
C_1—N_2—H1_2	118.4	H3_6—CG2_6—H5_6	109.5
CA_2—N_2—H1_2	118.4	H4_6—CG2_6—H5_6	109.5
N_2—CA_2—C_2	113.0 (2)	O_6—C_6—N_7	124.4 (3)
N_2—CA_2—CB_2	107.9 (2)	O_6—C_6—CA_6	118.8 (3)
C_2—CA_2—CB_2	112.4 (2)	N_7—C_6—CA_6	116.7 (3)
N_2—CA_2—H2_2	107.8	C_6—N_7—CA_7	120.8 (3)
C_2—CA_2—H2_2	107.8	C_6—N_7—H1_7	119.6
CB_2—CA_2—H2_2	107.8	CA_7—N_7—H1_7	119.6
OG1_2—CB_2—CG2_2	111.4 (3)	N_7—CA_7—C3_8	106.7 (2)
OG1_2—CB_2—CA_2	107.1 (2)	N_7—CA_7—CB_7	114.8 (3)
CG2_2—CB_2—CA_2	112.6 (3)	C3_8—CA_7—CB_7	114.2 (3)
OG1_2—CB_2—H3_2	108.6	N_7—CA_7—H2_7	106.9
CG2_2—CB_2—H3_2	108.6	C3_8—CA_7—H2_7	106.9
CA_2—CB_2—H3_2	108.6	CB_7—CA_7—H2_7	106.9
CB_2—OG1_2—H4_2	109.4 (2)	CG1_7—CB_7—CA_7	112.5 (3)
CB_2—CG2_2—H5_2	109.5	CG1_7—CB_7—CG2_7	112.7 (3)
CB_2—CG2_2—H6_2	109.5	CA_7—CB_7—CG2_7	109.1 (3)
H5_2—CG2_2—H6_2	109.5	CG1_7—CB_7—H3_7	107.4
CB_2—CG2_2—H7_2	109.5	CA_7—CB_7—H3_7	107.4
H5_2—CG2_2—H7_2	109.5	CG2_7—CB_7—H3_7	107.4
H6_2—CG2_2—H7_2	109.5	CB_7—CG1_7—H4_7	109.5
O_2—C_2—N_3	123.6 (3)	CB_7—CG1_7—H5_7	109.5
O_2—C_2—CA_2	119.7 (2)	H4_7—CG1_7—H5_7	109.5
N_3—C_2—CA_2	116.7 (2)	CB_7—CG1_7—H6_7	109.5
C_2—N_3—CA_3	121.4 (2)	H4_7—CG1_7—H6_7	109.5
C_2—N_3—H1_3	119.3	H5_7—CG1_7—H6_7	109.5
CA_3—N_3—H1_3	119.3	CB_7—CG2_7—H7_7	109.5
N_3—CA_3—C3_4	108.3 (2)	CB_7—CG2_7—H8_7	109.5
N_3—CA_3—CB_3	113.0 (2)	H7_7—CG2_7—H8_7	109.5
C3_4—CA_3—CB_3	115.1 (2)	CB_7—CG2_7—H9_7	109.5
N_3—CA_3—H2_3	106.7	H7_7—CG2_7—H9_7	109.5
C3_4—CA_3—H2_3	106.7	H8_7—CG2_7—H9_7	109.5
CB_3—CA_3—H2_3	106.7	N_8—C3_8—CA_7	121.8 (2)
CG1_3—CB_3—CG2_3	110.6 (3)	N_8—C3_8—SG_8	113.7 (2)
CG1_3—CB_3—CA_3	108.7 (2)	CA_7—C3_8—SG_8	124.43 (19)
CG2_3—CB_3—CA_3	113.4 (2)	C3_8—N_8—CA_8	111.5 (2)
CG1_3—CB_3—H3_3	108.0	CB_8—CA_8—N_8	115.6 (2)
CG2_3—CB_3—H3_3	108.0	CB_8—CA_8—C_8	126.8 (3)
CA_3—CB_3—H3_3	108.0	N_8—CA_8—C_8	117.4 (2)
CB_3—CG1_3—H4_3	109.5	CA_8—CB_8—SG_8	109.5 (2)
CB_3—CG1_3—H5_3	109.5	CA_8—CB_8—H1_8	125.3
H4_3—CG1_3—H5_3	109.5	SG_8—CB_8—H1_8	125.3
CB_3—CG1_3—H6_3	109.5	CB_8—SG_8—C3_8	89.79 (14)
H4_3—CG1_3—H6_3	109.5	O_8—C_8—N_1	123.9 (2)
H5_3—CG1_3—H6_3	109.5	O_8—C_8—CA_8	122.2 (3)
CB_3—CG2_3—H7_3	109.5	N_1—C_8—CA_8	113.9 (2)
CB_3—CG2_3—H8_3	109.5	O1_9—C1_9—N1_9	127.1 (7)
H7_3—CG2_3—H8_3	109.5	O1_9—C1_9—H1_9	116.4
CB_3—CG2_3—H9_3	109.5	N1_9—C1_9—H1_9	116.4
H7_3—CG2_3—H9_3	109.5	C1_9—N1_9—C2_9	125.8 (5)
H8_3—CG2_3—H9_3	109.5	C1_9—N1_9—C3_9	117.8 (5)
N_4—C3_4—CA_3	123.3 (2)	C2_9—N1_9—C3_9	116.2 (4)
N_4—C3_4—SG_4	113.72 (19)	N1_9—C2_9—H2_9	109.5
CA_3—C3_4—SG_4	122.94 (19)	N1_9—C2_9—H3_9	109.5
C3_4—N_4—CA_4	110.8 (2)	H2_9—C2_9—H3_9	109.5
CB_4—CA_4—N_4	115.9 (2)	N1_9—C2_9—H4_9	109.5
CB_4—CA_4—C_4	122.8 (2)	H2_9—C2_9—H4_9	109.5
N_4—CA_4—C_4	121.2 (2)	H3_9—C2_9—H4_9	109.5
CA_4—CB_4—SG_4	109.3 (2)	N1_9—C3_9—H5_9	109.5
CA_4—CB_4—H1_4	125.3	N1_9—C3_9—H6_9	109.5
SG_4—CB_4—H1_4	125.3	H5_9—C3_9—H6_9	109.5
CB_4—SG_4—C3_4	90.21 (13)	N1_9—C3_9—H7_9	109.5
O_4—C_4—N_5	122.0 (2)	H5_9—C3_9—H7_9	109.5
O_4—C_4—CA_4	121.7 (2)	H6_9—C3_9—H7_9	109.5
N_5—C_4—CA_4	116.2 (2)	O1_10—C1_10—N1_10	126.9 (8)
C_4—N_5—CA_5	118.6 (2)	O1_10—C1_10—H1_10	116.5
C_4—N_5—H1_5	120.7	N1_10—C1_10—H1_10	116.5
CA_5—N_5—H1_5	120.7	C3_10—N1_10—C1_10	122.9 (10)
N_5—CA_5—C3_6	110.2 (2)	C3_10—N1_10—C2_10	120.1 (10)
N_5—CA_5—CB_5	111.4 (2)	C1_10—N1_10—C2_10	116.9 (6)
C3_6—CA_5—CB_5	111.8 (2)	N1_10—C2_10—H2_10	109.5
N_5—CA_5—H2_5	107.7	N1_10—C2_10—H3_10	109.5
C3_6—CA_5—H2_5	107.7	H2_10—C2_10—H3_10	109.5
CB_5—CA_5—H2_5	107.7	N1_10—C2_10—H4_10	109.5
CG2_5—CB_5—CG1_5	111.2 (3)	H2_10—C2_10—H4_10	109.5
CG2_5—CB_5—CA_5	111.7 (2)	H3_10—C2_10—H4_10	109.5
CG1_5—CB_5—CA_5	112.0 (2)	N1_10—C3_10—H5_10	109.5
CG2_5—CB_5—H3_5	107.2	N1_10—C3_10—H6_10	109.5
CG1_5—CB_5—H3_5	107.2	H5_10—C3_10—H6_10	109.5
CA_5—CB_5—H3_5	107.2	N1_10—C3_10—H7_10	109.5
CB_5—CG2_5—H4_5	109.5	H5_10—C3_10—H7_10	109.5
CB_5—CG2_5—H5_5	109.5	H6_10—C3_10—H7_10	109.5
C_8—N_1—CA_1—C_1	−74.9 (3)	N_5—CA_5—CB_5—CG1_5	−67.8 (3)
C_8—N_1—CA_1—CB_1	161.2 (2)	C3_6—CA_5—CB_5—CG1_5	168.4 (2)
N_1—CA_1—CB_1—CG2_1	177.4 (3)	CG2_5—CB_5—CG1_5—CD_5	59.3 (4)
C_1—CA_1—CB_1—CG2_1	55.7 (3)	CA_5—CB_5—CG1_5—CD_5	−66.5 (4)
N_1—CA_1—CB_1—CG1_1	−58.1 (3)	N_5—CA_5—C3_6—N_6	−42.2 (4)
C_1—CA_1—CB_1—CG1_1	−179.8 (2)	CB_5—CA_5—C3_6—N_6	82.3 (3)
CG2_1—CB_1—CG1_1—CD_1	−63.1 (4)	N_5—CA_5—C3_6—OG1_6	138.6 (2)
CA_1—CB_1—CG1_1—CD_1	174.2 (3)	CB_5—CA_5—C3_6—OG1_6	−96.9 (3)
N_1—CA_1—C_1—O_1	−64.0 (3)	OG1_6—C3_6—N_6—CA_6	−2.0 (4)
CB_1—CA_1—C_1—O_1	58.1 (3)	CA_5—C3_6—N_6—CA_6	178.8 (3)
N_1—CA_1—C_1—N_2	114.3 (2)	C3_6—N_6—CA_6—C_6	−116.9 (3)
CB_1—CA_1—C_1—N_2	−123.5 (2)	C3_6—N_6—CA_6—CB_6	6.3 (3)
O_1—C_1—N_2—CA_2	5.1 (4)	N_6—CA_6—CB_6—OG1_6	−8.1 (3)
CA_1—C_1—N_2—CA_2	−173.2 (2)	C_6—CA_6—CB_6—OG1_6	114.3 (3)
C_1—N_2—CA_2—C_2	68.9 (3)	N_6—CA_6—CB_6—CG2_6	109.5 (3)
C_1—N_2—CA_2—CB_2	−166.2 (2)	C_6—CA_6—CB_6—CG2_6	−128.1 (3)
N_2—CA_2—CB_2—OG1_2	−60.6 (3)	N_6—C3_6—OG1_6—CB_6	−3.7 (3)
C_2—CA_2—CB_2—OG1_2	64.7 (3)	CA_5—C3_6—OG1_6—CB_6	175.6 (2)
N_2—CA_2—CB_2—CG2_2	176.7 (2)	CG2_6—CB_6—OG1_6—C3_6	−113.8 (3)
C_2—CA_2—CB_2—CG2_2	−58.0 (3)	CA_6—CB_6—OG1_6—C3_6	7.1 (3)
N_2—CA_2—C_2—O_2	−161.3 (2)	N_6—CA_6—C_6—O_6	−138.7 (3)
CB_2—CA_2—C_2—O_2	76.2 (3)	CB_6—CA_6—C_6—O_6	103.0 (4)
N_2—CA_2—C_2—N_3	19.3 (3)	N_6—CA_6—C_6—N_7	42.5 (4)
CB_2—CA_2—C_2—N_3	−103.1 (3)	CB_6—CA_6—C_6—N_7	−75.8 (3)
O_2—C_2—N_3—CA_3	9.7 (4)	O_6—C_6—N_7—CA_7	23.6 (5)
CA_2—C_2—N_3—CA_3	−171.0 (2)	CA_6—C_6—N_7—CA_7	−157.8 (3)
C_2—N_3—CA_3—C3_4	115.5 (3)	C_6—N_7—CA_7—C3_8	101.5 (3)
C_2—N_3—CA_3—CB_3	−115.8 (3)	C_6—N_7—CA_7—CB_7	−130.9 (3)
N_3—CA_3—CB_3—CG1_3	59.5 (3)	N_7—CA_7—CB_7—CG1_7	−65.2 (4)
C3_4—CA_3—CB_3—CG1_3	−175.4 (2)	C3_8—CA_7—CB_7—CG1_7	58.4 (4)
N_3—CA_3—CB_3—CG2_3	−64.0 (3)	N_7—CA_7—CB_7—CG2_7	60.6 (3)
C3_4—CA_3—CB_3—CG2_3	61.1 (3)	C3_8—CA_7—CB_7—CG2_7	−175.7 (3)
N_3—CA_3—C3_4—N_4	−27.8 (4)	N_7—CA_7—C3_8—N_8	−13.2 (4)
CB_3—CA_3—C3_4—N_4	−155.3 (3)	CB_7—CA_7—C3_8—N_8	−141.2 (3)
N_3—CA_3—C3_4—SG_4	154.4 (2)	N_7—CA_7—C3_8—SG_8	171.0 (2)
CB_3—CA_3—C3_4—SG_4	26.9 (3)	CB_7—CA_7—C3_8—SG_8	43.1 (4)
CA_3—C3_4—N_4—CA_4	−178.3 (2)	CA_7—C3_8—N_8—CA_8	−175.1 (3)
SG_4—C3_4—N_4—CA_4	−0.4 (3)	SG_8—C3_8—N_8—CA_8	1.1 (3)
C3_4—N_4—CA_4—CB_4	0.2 (3)	C3_8—N_8—CA_8—CB_8	−1.7 (4)
C3_4—N_4—CA_4—C_4	178.8 (2)	C3_8—N_8—CA_8—C_8	173.4 (2)
N_4—CA_4—CB_4—SG_4	0.0 (3)	N_8—CA_8—CB_8—SG_8	1.4 (3)
C_4—CA_4—CB_4—SG_4	−178.6 (2)	C_8—CA_8—CB_8—SG_8	−173.1 (2)
CA_4—CB_4—SG_4—C3_4	−0.2 (2)	CA_8—CB_8—SG_8—C3_8	−0.6 (2)
N_4—C3_4—SG_4—CB_4	0.3 (2)	N_8—C3_8—SG_8—CB_8	−0.3 (2)
CA_3—C3_4—SG_4—CB_4	178.3 (2)	CA_7—C3_8—SG_8—CB_8	175.8 (3)
CB_4—CA_4—C_4—O_4	−3.7 (4)	CA_1—N_1—C_8—O_8	6.2 (4)
N_4—CA_4—C_4—O_4	177.8 (2)	CA_1—N_1—C_8—CA_8	−170.5 (2)
CB_4—CA_4—C_4—N_5	174.6 (3)	CB_8—CA_8—C_8—O_8	−5.2 (4)
N_4—CA_4—C_4—N_5	−3.9 (4)	N_8—CA_8—C_8—O_8	−179.6 (3)
O_4—C_4—N_5—CA_5	3.1 (4)	CB_8—CA_8—C_8—N_1	171.5 (3)
CA_4—C_4—N_5—CA_5	−175.2 (2)	N_8—CA_8—C_8—N_1	−2.9 (3)
C_4—N_5—CA_5—C3_6	−61.0 (3)	O1_9—C1_9—N1_9—C2_9	7.8 (11)
C_4—N_5—CA_5—CB_5	174.2 (2)	O1_9—C1_9—N1_9—C3_9	−177.6 (7)
N_5—CA_5—CB_5—CG2_5	166.7 (3)	O1_10—C1_10—N1_10—C3_10	179.9 (8)
C3_6—CA_5—CB_5—CG2_5	42.9 (3)	O1_10—C1_10—N1_10—C2_10	2.3 (10)