Cyclo-(-l-prolyl-l-valinyl-) from Burkholderia thailandensis MSMB43.

THE TITLE COMPOUND [SYSTEMATIC NAME: (3S,8aS)-3-isopropyl-hexa-hydro-pyrrolo-[1,2-a]pyrazine-1,4-dione], C(10)H(16)N(2)O(2),, is a newly isolated cyclic dipeptide from Burkholderia thailandensis MSMB43. There are two independent mol-ecules in the asymmetric unit. Two C atoms and their attached H atoms in the five-membered ring of one of the mol-ecules are disordered over two sets of sites in a 0.715 (5):0.285 (5) ratio. The two independent mol-ecules have the same configuration and the absolute configurations of the chiral centers were determined based on the observation of anomalous dispersion. In the crystal, two types of N-H⋯O hydrogen bonds link pairs of independent mol-ecules.

Related literature

For general background to secondary metabolites from B. thailandensis, see: Knappe et al. (2008 ▶); Nguyen et al. (2008 ▶); Seyedsayamdost et al. (2010 ▶); Ishida et al. (2010 ▶); Klausmeyer et al. (2011 ▶); Biggins et al. (2011 ▶); Wang et al. (2011 ▶, 2012 ▶); Ishida et al. (2012 ▶). For isolation of the title compound from other microorganisms, see: Chen (1960 ▶); Schmitz et al. (1983 ▶); Jayatilake et al. (1996 ▶); Ginz & Engelhardt (2000 ▶); Qi et al. (2009 ▶); Wang et al. (2010 ▶); Park et al. (2006 ▶). For the biological activity of the title compound, see: Holden et al. (1999 ▶); Fdhila et al. (2003 ▶). For large-scale genome sequencing, see: Mukhopadhyay et al. (2010 ▶); Yu et al. (2006 ▶); Zhuo et al. (2012 ▶). For our work on obtaining natural products from B. thailandensis MSMB43, see: Liu et al. (2012 ▶).

Experimental

Crystal data

C10H16N2O2

M = 196.25

Orthorhombic,

a = 5.6227 (1) Å

b = 10.2571 (2) Å

c = 34.2115 (6) Å

V = 1973.07 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.76 mm−1

T = 100 K

0.22 × 0.14 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.851, T max = 0.928

28285 measured reflections

3668 independent reflections

3354 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.075

S = 1.02

3668 reflections

271 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1481 Friedel pairs

Flack parameter: 0.05 (17)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043000/ff2084sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043000/ff2084Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043000/ff2084Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043000/ff2084Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H16N2O2	F(000) = 848
Mr = 196.25	Dx = 1.321 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 999 reflections
a = 5.6227 (1) Å	θ = 2.6–69.5°
b = 10.2571 (2) Å	µ = 0.76 mm−1
c = 34.2115 (6) Å	T = 100 K
V = 1973.07 (6) Å3	Needle, colourless
Z = 8	0.22 × 0.14 × 0.10 mm

Bruker APEXII area-detector diffractometer	3668 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
0.50° ω and 0.5 ° φ scans	θmax = 69.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
Tmin = 0.851, Tmax = 0.928	k = −12→12
28285 measured reflections	l = −40→41

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.438P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3668 reflections	Δρmax = 0.30 e Å−3
271 parameters	Δρmin = −0.23 e Å−3
3 restraints	Absolute structure: Flack (1983), 1481 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (17)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.0686 (2)	0.57786 (10)	0.42809 (3)	0.0185 (2)
O2	0.6845 (2)	0.29334 (10)	0.46538 (3)	0.0189 (2)
N1	0.1607 (2)	0.39828 (12)	0.41718 (4)	0.0158 (3)
H1	0.120 (3)	0.3984 (17)	0.3926 (6)	0.019*
N2	0.4056 (2)	0.44278 (12)	0.48284 (4)	0.0151 (3)
C1	0.0698 (3)	0.49203 (15)	0.43957 (4)	0.0154 (3)
C2	0.1570 (3)	0.48683 (15)	0.48164 (4)	0.0152 (3)
H2	0.0559	0.4246	0.4968	0.018*
C3	0.1676 (3)	0.61678 (15)	0.50308 (5)	0.0177 (3)
H3A	0.0138	0.6373	0.5157	0.021*
H3B	0.2109	0.6886	0.4851	0.021*
C4	0.3622 (3)	0.59338 (16)	0.53340 (4)	0.0179 (3)
H4A	0.4259	0.6767	0.5436	0.021*
H4B	0.3025	0.5404	0.5555	0.021*
C5	0.5497 (3)	0.51970 (15)	0.51009 (4)	0.0167 (3)
H5A	0.6562	0.5804	0.4960	0.020*
H5B	0.6463	0.4628	0.5272	0.020*
C6	0.4837 (3)	0.34091 (14)	0.46205 (4)	0.0155 (3)
C7	0.2933 (3)	0.28844 (14)	0.43410 (4)	0.0155 (3)
H7	0.1787	0.2360	0.4500	0.019*
C8	0.3954 (3)	0.19864 (15)	0.40270 (4)	0.0175 (3)
H8	0.4958	0.1321	0.4163	0.021*
C9	0.1969 (3)	0.12534 (16)	0.38147 (5)	0.0215 (3)
H9A	0.1029	0.1870	0.3660	0.032*
H9B	0.0940	0.0825	0.4007	0.032*
H9C	0.2668	0.0596	0.3641	0.032*
C10	0.5556 (3)	0.27055 (17)	0.37385 (5)	0.0218 (3)
H10A	0.4603	0.3323	0.3586	0.033*
H10B	0.6305	0.2075	0.3562	0.033*
H10C	0.6790	0.3180	0.3882	0.033*
O1A	1.0544 (2)	0.43773 (11)	0.33589 (3)	0.0214 (2)
O2A	0.4323 (2)	0.77776 (12)	0.27683 (3)	0.0320 (3)
N1A	0.7596 (2)	0.58471 (13)	0.34599 (4)	0.0186 (3)
H1A	0.799 (3)	0.5861 (18)	0.3720 (6)	0.022*
N2A	0.6766 (3)	0.60603 (14)	0.26780 (4)	0.0221 (3)
C1A	0.8856 (3)	0.50385 (15)	0.32357 (4)	0.0172 (3)
C2A	0.8103 (3)	0.49229 (16)	0.28135 (4)	0.0190 (3)
H2A	0.7014	0.4155	0.2795	0.023*	0.715 (5)
H2B	0.7274	0.4081	0.2756	0.023*	0.285 (5)
C3A	1.0062 (5)	0.4726 (3)	0.25090 (7)	0.0201 (8)	0.715 (5)
H3C	0.9797	0.3906	0.2363	0.024*	0.715 (5)
H3D	1.1637	0.4680	0.2638	0.024*	0.715 (5)
C4A	0.9952 (6)	0.5904 (3)	0.22307 (7)	0.0283 (7)	0.715 (5)
H4C	1.0389	0.5656	0.1960	0.034*	0.715 (5)
H4D	1.1001	0.6619	0.2320	0.034*	0.715 (5)
C3B	1.0460 (10)	0.5041 (11)	0.25504 (12)	0.0201 (8)	0.285 (5)
H3E	1.1567	0.5726	0.2642	0.024*	0.285 (5)
H3F	1.1306	0.4201	0.2518	0.024*	0.285 (5)
C4B	0.9032 (14)	0.5445 (9)	0.21869 (9)	0.0283 (7)	0.285 (5)
H4E	1.0131	0.5846	0.1996	0.034*	0.285 (5)
H4F	0.8355	0.4652	0.2065	0.034*	0.285 (5)
C5A	0.7235 (3)	0.62958 (18)	0.22612 (5)	0.0281 (4)
H5C	0.6982	0.7222	0.2191	0.034*	0.715 (5)
H5D	0.6228	0.5738	0.2093	0.034*	0.715 (5)
H5E	0.7743	0.7210	0.2220	0.034*	0.285 (5)
H5F	0.5790	0.6131	0.2104	0.034*	0.285 (5)
C6A	0.5464 (3)	0.68536 (16)	0.28998 (5)	0.0218 (4)
C7A	0.5431 (3)	0.65377 (15)	0.33383 (4)	0.0187 (3)
H7A	0.4041	0.5954	0.3390	0.022*
C8A	0.5085 (3)	0.77939 (15)	0.35758 (4)	0.0189 (3)
H8A	0.3758	0.8289	0.3450	0.023*
C9A	0.4322 (3)	0.75127 (17)	0.39963 (5)	0.0234 (4)
H9D	0.5601	0.7050	0.4133	0.035*
H9E	0.2885	0.6972	0.3995	0.035*
H9F	0.3990	0.8336	0.4131	0.035*
C10A	0.7283 (3)	0.86638 (17)	0.35596 (5)	0.0262 (4)
H10D	0.6927	0.9504	0.3683	0.039*
H10E	0.7740	0.8805	0.3286	0.039*
H10F	0.8595	0.8241	0.3699	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0189 (5)	0.0192 (5)	0.0175 (5)	0.0049 (5)	−0.0028 (5)	−0.0005 (4)
O2	0.0154 (5)	0.0211 (5)	0.0203 (5)	0.0032 (5)	−0.0027 (5)	−0.0004 (5)
N1	0.0175 (7)	0.0179 (6)	0.0119 (6)	0.0029 (6)	−0.0035 (5)	0.0006 (5)
N2	0.0145 (6)	0.0170 (6)	0.0138 (6)	0.0008 (5)	−0.0021 (5)	−0.0011 (5)
C1	0.0140 (7)	0.0174 (7)	0.0148 (7)	−0.0030 (7)	−0.0006 (6)	0.0004 (6)
C2	0.0138 (7)	0.0172 (7)	0.0147 (7)	0.0002 (6)	0.0006 (6)	0.0001 (6)
C3	0.0151 (7)	0.0201 (7)	0.0178 (7)	0.0007 (6)	−0.0001 (6)	−0.0028 (6)
C4	0.0160 (8)	0.0216 (7)	0.0161 (7)	−0.0018 (7)	−0.0014 (6)	−0.0019 (6)
C5	0.0162 (7)	0.0184 (7)	0.0155 (7)	−0.0020 (7)	−0.0034 (6)	0.0001 (6)
C6	0.0173 (8)	0.0152 (7)	0.0139 (7)	−0.0016 (6)	−0.0007 (6)	0.0036 (6)
C7	0.0169 (8)	0.0145 (7)	0.0151 (7)	0.0005 (6)	−0.0001 (6)	0.0025 (6)
C8	0.0189 (8)	0.0167 (7)	0.0169 (7)	0.0023 (6)	−0.0022 (6)	−0.0004 (6)
C9	0.0243 (8)	0.0211 (8)	0.0190 (8)	−0.0011 (7)	0.0001 (7)	−0.0048 (7)
C10	0.0191 (8)	0.0266 (8)	0.0198 (8)	0.0015 (7)	0.0021 (7)	−0.0020 (7)
O1A	0.0228 (6)	0.0242 (6)	0.0173 (5)	0.0066 (5)	−0.0020 (5)	0.0014 (5)
O2A	0.0418 (7)	0.0346 (7)	0.0197 (6)	0.0179 (6)	−0.0074 (6)	0.0000 (5)
N1A	0.0206 (7)	0.0212 (7)	0.0139 (6)	0.0020 (6)	−0.0046 (5)	−0.0001 (6)
N2A	0.0271 (7)	0.0247 (7)	0.0146 (6)	0.0064 (6)	−0.0050 (6)	−0.0003 (5)
C1A	0.0181 (8)	0.0158 (7)	0.0177 (7)	−0.0024 (6)	−0.0013 (6)	0.0010 (6)
C2A	0.0209 (8)	0.0191 (7)	0.0169 (8)	0.0005 (7)	−0.0020 (7)	0.0001 (7)
C3A	0.0151 (12)	0.0287 (18)	0.0164 (9)	−0.0045 (11)	−0.0045 (9)	−0.0028 (9)
C4A	0.0290 (18)	0.0287 (16)	0.0271 (11)	0.0011 (12)	0.0122 (11)	0.0109 (11)
C3B	0.0151 (12)	0.0287 (18)	0.0164 (9)	−0.0045 (11)	−0.0045 (9)	−0.0028 (9)
C4B	0.0290 (18)	0.0287 (16)	0.0271 (11)	0.0011 (12)	0.0122 (11)	0.0109 (11)
C5A	0.0412 (11)	0.0307 (9)	0.0124 (8)	0.0064 (8)	−0.0042 (7)	0.0000 (7)
C6A	0.0223 (9)	0.0243 (8)	0.0187 (8)	0.0034 (8)	−0.0070 (7)	−0.0028 (7)
C7A	0.0174 (8)	0.0204 (8)	0.0182 (7)	0.0004 (6)	−0.0025 (7)	0.0026 (6)
C8A	0.0191 (8)	0.0210 (8)	0.0166 (7)	0.0030 (7)	−0.0003 (6)	0.0006 (6)
C9A	0.0219 (8)	0.0287 (9)	0.0197 (8)	0.0035 (7)	0.0021 (7)	0.0002 (7)
C10A	0.0331 (10)	0.0219 (8)	0.0236 (8)	−0.0068 (8)	0.0048 (8)	−0.0012 (7)

O1—C1	1.2390 (19)	N2A—C6A	1.332 (2)
O2—C6	1.2354 (19)	N2A—C2A	1.463 (2)
N1—C1	1.331 (2)	N2A—C5A	1.470 (2)
N1—C7	1.4698 (19)	C1A—C2A	1.510 (2)
N1—H1	0.872 (19)	C2A—C3A	1.530 (3)
N2—C6	1.3381 (19)	C2A—C3B	1.607 (4)
N2—C5	1.4656 (19)	C2A—H2A	1.0000
N2—C2	1.469 (2)	C2A—H2B	1.0000
C1—C2	1.521 (2)	C3A—C4A	1.539 (3)
C2—C3	1.523 (2)	C3A—H3C	0.9900
C2—H2	1.0000	C3A—H3D	0.9900
C3—C4	1.527 (2)	C4A—C5A	1.583 (4)
C3—H3A	0.9900	C4A—H4C	0.9900
C3—H3B	0.9900	C4A—H4D	0.9900
C4—C5	1.523 (2)	C3B—C4B	1.537 (3)
C4—H4A	0.9900	C3B—H3E	0.9900
C4—H4B	0.9900	C3B—H3F	0.9900
C5—H5A	0.9900	C4B—C5A	1.359 (7)
C5—H5B	0.9900	C4B—H4E	0.9900
C6—C7	1.533 (2)	C4B—H4F	0.9900
C7—C8	1.527 (2)	C5A—H5C	0.9900
C7—H7	1.0000	C5A—H5D	0.9900
C8—C10	1.526 (2)	C5A—H5E	0.9900
C8—C9	1.529 (2)	C5A—H5F	0.9900
C8—H8	1.0000	C6A—C7A	1.535 (2)
C9—H9A	0.9800	C7A—C8A	1.536 (2)
C9—H9B	0.9800	C7A—H7A	1.0000
C9—H9C	0.9800	C8A—C10A	1.525 (2)
C10—H10A	0.9800	C8A—C9A	1.528 (2)
C10—H10B	0.9800	C8A—H8A	1.0000
C10—H10C	0.9800	C9A—H9D	0.9800
O1A—C1A	1.2402 (19)	C9A—H9E	0.9800
O2A—C6A	1.230 (2)	C9A—H9F	0.9800
N1A—C1A	1.333 (2)	C10A—H10D	0.9800
N1A—C7A	1.469 (2)	C10A—H10E	0.9800
N1A—H1A	0.916 (19)	C10A—H10F	0.9800
C1—N1—C7	121.45 (13)	N2A—C2A—C3B	100.7 (3)
C1—N1—H1	116.9 (12)	C1A—C2A—C3B	107.4 (3)
C7—N1—H1	121.0 (12)	C3A—C2A—C3B	15.0 (4)
C6—N2—C5	125.23 (13)	N2A—C2A—H2A	107.1
C6—N2—C2	122.52 (13)	C1A—C2A—H2A	107.1
C5—N2—C2	112.22 (12)	C3A—C2A—H2A	107.1
O1—C1—N1	124.88 (14)	N2A—C2A—H2B	112.8
O1—C1—C2	121.83 (13)	C1A—C2A—H2B	112.7
N1—C1—C2	113.28 (13)	C3B—C2A—H2B	109.8
N2—C2—C1	110.11 (12)	C2A—C3A—C4A	106.77 (18)
N2—C2—C3	102.62 (12)	C2A—C3A—H3C	110.4
C1—C2—C3	115.95 (13)	C4A—C3A—H3C	110.4
N2—C2—H2	109.3	C2A—C3A—H3D	110.4
C1—C2—H2	109.3	C4A—C3A—H3D	110.4
C3—C2—H2	109.3	H3C—C3A—H3D	108.6
C2—C3—C4	102.58 (13)	C3A—C4A—C5A	101.4 (2)
C2—C3—H3A	111.3	C3A—C4A—H4C	111.5
C4—C3—H3A	111.3	C5A—C4A—H4C	111.5
C2—C3—H3B	111.3	C3A—C4A—H4D	111.5
C4—C3—H3B	111.3	C5A—C4A—H4D	111.5
H3A—C3—H3B	109.2	H4C—C4A—H4D	109.3
C5—C4—C3	102.61 (12)	C4B—C3B—C2A	92.4 (3)
C5—C4—H4A	111.2	C4B—C3B—H3E	113.2
C3—C4—H4A	111.2	C2A—C3B—H3E	113.2
C5—C4—H4B	111.2	C4B—C3B—H3F	113.2
C3—C4—H4B	111.2	C2A—C3B—H3F	113.2
H4A—C4—H4B	109.2	H3E—C3B—H3F	110.6
N2—C5—C4	102.57 (12)	C5A—C4B—C3B	114.2 (4)
N2—C5—H5A	111.3	C5A—C4B—H4E	108.7
C4—C5—H5A	111.3	C3B—C4B—H4E	108.7
N2—C5—H5B	111.3	C5A—C4B—H4F	108.7
C4—C5—H5B	111.3	C3B—C4B—H4F	108.7
H5A—C5—H5B	109.2	H4E—C4B—H4F	107.6
O2—C6—N2	124.02 (14)	C4B—C5A—N2A	102.1 (2)
O2—C6—C7	123.85 (14)	N2A—C5A—C4A	101.27 (15)
N2—C6—C7	112.11 (13)	N2A—C5A—H5C	111.5
N1—C7—C8	112.07 (12)	C4A—C5A—H5C	111.5
N1—C7—C6	109.31 (12)	N2A—C5A—H5D	111.5
C8—C7—C6	112.84 (13)	C4A—C5A—H5D	111.5
N1—C7—H7	107.5	H5C—C5A—H5D	109.3
C8—C7—H7	107.5	C4B—C5A—H5E	111.5
C6—C7—H7	107.5	N2A—C5A—H5E	110.3
C10—C8—C7	112.67 (13)	C4B—C5A—H5F	113.5
C10—C8—C9	111.19 (13)	N2A—C5A—H5F	110.7
C7—C8—C9	110.87 (13)	H5E—C5A—H5F	108.7
C10—C8—H8	107.3	O2A—C6A—N2A	123.30 (15)
C7—C8—H8	107.3	O2A—C6A—C7A	120.94 (14)
C9—C8—H8	107.3	N2A—C6A—C7A	115.76 (14)
C8—C9—H9A	109.5	N1A—C7A—C6A	111.64 (13)
C8—C9—H9B	109.5	N1A—C7A—C8A	111.08 (13)
H9A—C9—H9B	109.5	C6A—C7A—C8A	109.98 (13)
C8—C9—H9C	109.5	N1A—C7A—H7A	108.0
H9A—C9—H9C	109.5	C6A—C7A—H7A	108.0
H9B—C9—H9C	109.5	C8A—C7A—H7A	108.0
C8—C10—H10A	109.5	C10A—C8A—C9A	111.84 (14)
C8—C10—H10B	109.5	C10A—C8A—C7A	111.64 (13)
H10A—C10—H10B	109.5	C9A—C8A—C7A	112.04 (13)
C8—C10—H10C	109.5	C10A—C8A—H8A	107.0
H10A—C10—H10C	109.5	C9A—C8A—H8A	107.0
H10B—C10—H10C	109.5	C7A—C8A—H8A	107.0
C1A—N1A—C7A	125.26 (13)	C8A—C9A—H9D	109.5
C1A—N1A—H1A	116.0 (12)	C8A—C9A—H9E	109.5
C7A—N1A—H1A	118.0 (12)	H9D—C9A—H9E	109.5
C6A—N2A—C2A	126.07 (13)	C8A—C9A—H9F	109.5
C6A—N2A—C5A	123.44 (14)	H9D—C9A—H9F	109.5
C2A—N2A—C5A	110.25 (13)	H9E—C9A—H9F	109.5
O1A—C1A—N1A	123.44 (14)	C8A—C10A—H10D	109.5
O1A—C1A—C2A	119.79 (14)	C8A—C10A—H10E	109.5
N1A—C1A—C2A	116.76 (13)	H10D—C10A—H10E	109.5
N2A—C2A—C1A	112.62 (13)	C8A—C10A—H10F	109.5
N2A—C2A—C3A	105.04 (15)	H10D—C10A—H10F	109.5
C1A—C2A—C3A	117.37 (17)	H10E—C10A—H10F	109.5
C7—N1—C1—O1	−170.29 (14)	C5A—N2A—C2A—C3A	18.7 (2)
C7—N1—C1—C2	11.1 (2)	C6A—N2A—C2A—C3B	−141.0 (4)
C6—N2—C2—C1	−45.57 (18)	C5A—N2A—C2A—C3B	33.5 (4)
C5—N2—C2—C1	136.54 (13)	O1A—C1A—C2A—N2A	−158.55 (15)
C6—N2—C2—C3	−169.60 (13)	N1A—C1A—C2A—N2A	22.8 (2)
C5—N2—C2—C3	12.51 (15)	O1A—C1A—C2A—C3A	−36.4 (2)
O1—C1—C2—N2	−143.76 (14)	N1A—C1A—C2A—C3A	145.00 (17)
N1—C1—C2—N2	34.95 (18)	O1A—C1A—C2A—C3B	−48.6 (4)
O1—C1—C2—C3	−27.8 (2)	N1A—C1A—C2A—C3B	132.8 (4)
N1—C1—C2—C3	150.87 (14)	N2A—C2A—C3A—C4A	7.3 (3)
N2—C2—C3—C4	−33.24 (14)	C1A—C2A—C3A—C4A	−118.7 (3)
C1—C2—C3—C4	−153.30 (13)	C2A—C3A—C4A—C5A	−27.8 (3)
C2—C3—C4—C5	42.04 (15)	N2A—C2A—C3B—C4B	−40.4 (7)
C6—N2—C5—C4	−164.35 (13)	C1A—C2A—C3B—C4B	−158.4 (5)
C2—N2—C5—C4	13.47 (16)	C2A—C3B—C4B—C5A	41.1 (9)
C3—C4—C5—N2	−33.83 (15)	C3B—C4B—C5A—N2A	−23.0 (8)
C5—N2—C6—O2	5.3 (2)	C6A—N2A—C5A—C4B	166.1 (4)
C2—N2—C6—O2	−172.35 (14)	C2A—N2A—C5A—C4B	−8.6 (5)
C5—N2—C6—C7	−175.76 (13)	C6A—N2A—C5A—C4A	138.76 (19)
C2—N2—C6—C7	6.64 (19)	C2A—N2A—C5A—C4A	−35.9 (2)
C1—N1—C7—C8	−175.93 (14)	C3A—C4A—C5A—N2A	37.7 (3)
C1—N1—C7—C6	−50.06 (19)	C2A—N2A—C6A—O2A	−177.98 (16)
O2—C6—C7—N1	−142.09 (14)	C5A—N2A—C6A—O2A	8.2 (3)
N2—C6—C7—N1	38.92 (17)	C2A—N2A—C6A—C7A	1.2 (2)
O2—C6—C7—C8	−16.7 (2)	C5A—N2A—C6A—C7A	−172.63 (15)
N2—C6—C7—C8	164.34 (13)	C1A—N1A—C7A—C6A	−31.1 (2)
N1—C7—C8—C10	56.61 (17)	C1A—N1A—C7A—C8A	−154.21 (15)
C6—C7—C8—C10	−67.31 (17)	O2A—C6A—C7A—N1A	−154.28 (15)
N1—C7—C8—C9	−68.72 (16)	N2A—C6A—C7A—N1A	26.5 (2)
C6—C7—C8—C9	167.36 (13)	O2A—C6A—C7A—C8A	−30.5 (2)
C7A—N1A—C1A—O1A	−172.92 (14)	N2A—C6A—C7A—C8A	150.31 (15)
C7A—N1A—C1A—C2A	5.6 (2)	N1A—C7A—C8A—C10A	53.83 (17)
C6A—N2A—C2A—C1A	−26.9 (2)	C6A—C7A—C8A—C10A	−70.28 (17)
C5A—N2A—C2A—C1A	147.63 (14)	N1A—C7A—C8A—C9A	−72.51 (17)
C6A—N2A—C2A—C3A	−155.8 (2)	C6A—C7A—C8A—C9A	163.39 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Ai	0.872 (19)	2.016 (19)	2.8734 (17)	167.7 (17)
N1A—H1A···O1ii	0.916 (19)	2.06 (2)	2.9710 (17)	172.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1A i	0.872 (19)	2.016 (19)	2.8734 (17)	167.7 (17)
N1A—H1A⋯O1ii	0.916 (19)	2.06 (2)	2.9710 (17)	172.3 (17)

Symmetry codes: (i) ; (ii) .