(1S,2E,6R,7aR)-1,6-Dihy-droxy-2-(4-nitro-benzyl-idene)-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one.

The crystal structure of the title compound, C(14)H(14)N(2)O(5), contains two distinct conformers in the asymmetric unit. The compound has three defined stereocenters, two of them contiguous, and a C=C double bond with an E conformation. The stereocenters exhibit the same chirality in both conformers, with significant differences in the conformation of the five-membered rings of the pyrrolizine unit (both either in a twist or in an envelope form) and in the dihedral angles between the corresponding mean planes and the benzene rings. A prominent feature is a change from almost coplanar rings in one conformer to a new conformation in the second conformer, in which the mean plane of a five-membered ring is almost perpendicular to the benzene ring, with a dihedral angle 87.19 (8)°; the corresponding angle in the first conformer is 14.02 (10)°. In the crystal, molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds. Crystallographic data were essential to confirm the configuration of the double bond, which was unclear from the available two-dimensional NMR data. In addition, reliable Flack and Hooft parameters were obtained, allowing for the correct absolute structure to be determined.

Related literature

For the preparation of the title compound, see: Freire et al. (2011 ▶). For the use of this type of compound as LFA-1 (Lymphocyte Function-Associated Anti­gen-1) inhibitors, see: Baumann (2007 ▶). For related structures, see: Oliveira et al. (2012a ▶,b ▶).

Experimental

Crystal data

C14H14N2O5

M = 290.27

Monoclinic,

a = 6.8289 (6) Å

b = 7.0433 (6) Å

c = 26.618 (3) Å

β = 92.335 (4)°

V = 1279.2 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.98 mm−1

T = 100 K

0.39 × 0.23 × 0.06 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

Absorption correction: numerical (SADABS; Bruker, 2010 ▶) T min = 0.844, T max = 1.000

41060 measured reflections

4038 independent reflections

3986 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.067

S = 1.01

4038 reflections

383 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶) and Hooft et al. (2008 ▶); Hooft parameter = 0.04(4), 1539 Bijvoet pairs

Flack parameter: 0.03 (11)

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018235/pv2525sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018235/pv2525Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018235/pv2525Isup3.cml

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

C14H14N2O5	F(000) = 608
Mr = 290.27	Dx = 1.507 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 6.8289 (6) Å	Cell parameters from 4038 reflections
b = 7.0433 (6) Å	θ = 1.7–67.8°
c = 26.618 (3) Å	µ = 0.98 mm−1
β = 92.335 (4)°	T = 100 K
V = 1279.2 (2) Å3	Plate, orange
Z = 4	0.39 × 0.23 × 0.06 mm

Bruker Kappa APEXII DUO diffractometer	4038 independent reflections
Radiation source: fine-focus sealed tube	3986 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Bruker APEX CCD area–detector scans	θmax = 67.8°, θmin = 1.7°
Absorption correction: numerical (SADABS; Bruker, 2010)	h = −8→8
Tmin = 0.844, Tmax = 1.000	k = −8→6
41060 measured reflections	l = −31→31

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)] = 0.025	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.3034P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4038 reflections	Δρmax = 0.15 e Å−3
383 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983) and Hooft et al. (2008); Hooft parameter = 0.04(4), 1539 Bijvoet pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (11)

Experimental. [α]D20 + 28° (c 2, MeOH); IR (Film, νmax): 3308, 2974, 2924, 2864, 1699, 1671, 1644, 1596, 1523, 1513, 1435, 1381, 1346, 1314, 1264, 1244, 1220, 1202, 1133, 1104, 1075, 1055 cm-1; 1H NMR (400 MHz, CD3OD) δ 1.49 (ddd, J = 13.2, 8.3, 5.1 Hz, 1H, H-7 A); 2.49 (ddd, J = 13.3, 7.4, 6.2 Hz, 1H, H-7B); 3.38 (dd, J = 12.4, 5.8 Hz, 1H, H-5 A); 3.68 (dd, J = 12.4, 3.0 Hz, 1H, H-5B); 3.80 (td, J = 8.1, 2.4 Hz, 1H, H-7 C); 4.56 (qd, J = 5.8, 3.3 Hz 1H, H-6); 5.01 (t, J = 2.4 Hz, 1H, H-1); 7.45 (d, J = 2.3 Hz, 1H, H-4); 8.01 (d, J = 8.8 Hz, 2H, Ar); 8.26 (d, J = 8.9 Hz, 2H, Ar); 13C NMR (62.5 MHz, CD3CN) 39.2; 53.3; 68.4; 71.5; 72.5; 124.3; 132.4; 133.2; 140.5; 141.8; 148.6; 170.9; HRMS (ESI-TOF) m/z Calc. for C14H15N2O5 [M + H]+: 291.0981. Found 291.0989.

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
O4	0.39324 (16)	0.4194 (2)	1.13861 (4)	0.0321 (3)
O3	1.01737 (15)	0.58119 (18)	0.71964 (4)	0.0225 (2)
H3	1.1038	0.5564	0.7002	0.034*
O5	0.64579 (19)	0.4992 (2)	1.18584 (4)	0.0403 (3)
O2	1.35576 (15)	0.51910 (18)	0.90371 (4)	0.0242 (3)
O1	0.69151 (14)	0.31660 (18)	0.90951 (4)	0.0229 (2)
H1A	0.5821	0.3645	0.9071	0.034*
O4'	−0.02923 (16)	0.27989 (18)	0.37824 (4)	0.0276 (3)
O3'	0.64995 (14)	−0.31144 (17)	0.68320 (4)	0.0213 (2)
H3'	0.7590	−0.3523	0.6914	0.032*
O5'	−0.20844 (14)	0.44237 (19)	0.42810 (4)	0.0253 (2)
O2'	0.89538 (14)	0.19376 (18)	0.63315 (4)	0.0246 (2)
O1'	0.32974 (14)	0.45702 (17)	0.66785 (4)	0.0208 (2)
H1A'	0.4302	0.5197	0.6722	0.031*
N1	1.11842 (16)	0.4299 (2)	0.84513 (4)	0.0190 (3)
N2'	−0.05497 (17)	0.3612 (2)	0.41818 (5)	0.0200 (3)
C8'	0.3952 (2)	0.3245 (2)	0.53145 (5)	0.0186 (3)
N1'	0.67054 (17)	0.15506 (19)	0.69496 (5)	0.0182 (3)
N2	0.5662 (2)	0.4640 (2)	1.14448 (5)	0.0268 (3)
C11	0.6877 (2)	0.4734 (2)	1.10041 (6)	0.0230 (3)
C10	0.6000 (2)	0.5089 (3)	1.05377 (6)	0.0243 (3)
H10	0.4657	0.5303	1.0504	0.029*
C9	0.7149 (2)	0.5122 (3)	1.01205 (6)	0.0231 (3)
H9	0.6577	0.5391	0.9805	0.028*
C8	0.9165 (2)	0.4754 (2)	1.01693 (5)	0.0204 (3)
C4	1.0493 (2)	0.4734 (2)	0.97498 (5)	0.0203 (3)
H4	1.1813	0.4820	0.9848	0.024*
C2	1.0161 (2)	0.4615 (2)	0.92537 (5)	0.0182 (3)
C1	0.83077 (19)	0.4455 (2)	0.89178 (5)	0.0181 (3)
H1	0.7706	0.5712	0.8877	0.022*
C7A	0.9103 (2)	0.3801 (2)	0.84114 (5)	0.0184 (3)
H7C	0.8963	0.2421	0.8379	0.022*
C7	0.84455 (19)	0.4745 (3)	0.79203 (5)	0.0200 (3)
H7A	0.8157	0.6079	0.7970	0.024*
H7B	0.7298	0.4122	0.7770	0.024*
C6	1.0236 (2)	0.4485 (3)	0.75953 (5)	0.0197 (3)
H6	1.0251	0.3191	0.7460	0.024*
C12	0.8871 (2)	0.4445 (3)	1.10728 (6)	0.0242 (3)
H12	0.9440	0.4252	1.1392	0.029*
C13	0.9999 (2)	0.4452 (3)	1.06502 (6)	0.0224 (3)
H13	1.1343	0.4251	1.0689	0.027*
C5	1.2005 (2)	0.4771 (3)	0.79686 (5)	0.0219 (3)
H5A	1.3075	0.3927	0.7893	0.026*
H5B	1.2468	0.6073	0.7964	0.026*
C3	1.1863 (2)	0.4727 (2)	0.89175 (5)	0.0187 (3)
C11'	0.1040 (2)	0.3571 (2)	0.45687 (6)	0.0184 (3)
C10'	0.0645 (2)	0.4121 (2)	0.50562 (5)	0.0185 (3)
H10'	−0.0580	0.4598	0.5130	0.022*
C9'	0.2104 (2)	0.3945 (2)	0.54290 (6)	0.0193 (3)
H9'	0.1857	0.4294	0.5757	0.023*
C4'	0.5558 (2)	0.2916 (2)	0.56866 (5)	0.0193 (3)
H4'	0.6804	0.2868	0.5558	0.023*
C2'	0.5490 (2)	0.2677 (2)	0.61826 (5)	0.0179 (3)
C3'	0.7287 (2)	0.2047 (2)	0.64785 (5)	0.0186 (3)
C5'	0.7559 (2)	−0.0070 (2)	0.72222 (6)	0.0220 (3)
H5A'	0.7835	0.0247	0.7573	0.026*
H5B'	0.8765	−0.0475	0.7074	0.026*
C6'	0.5976 (2)	−0.1640 (2)	0.71715 (5)	0.0190 (3)
H6'	0.5717	−0.2175	0.7502	0.023*
C7'	0.4137 (2)	−0.0660 (3)	0.69485 (5)	0.0200 (3)
H7A'	0.3879	−0.1059	0.6603	0.024*
H7B'	0.3006	−0.0968	0.7142	0.024*
C7A'	0.4561 (2)	0.1466 (2)	0.69725 (5)	0.0176 (3)
H7C'	0.4138	0.1998	0.7291	0.021*
C1'	0.3793 (2)	0.2681 (2)	0.65274 (5)	0.0169 (3)
H1'	0.2651	0.2069	0.6362	0.020*
C13'	0.4305 (2)	0.2780 (2)	0.48130 (6)	0.0199 (3)
H13'	0.5548	0.2371	0.4732	0.024*
C12'	0.2860 (2)	0.2915 (2)	0.44377 (5)	0.0198 (3)
H12'	0.3100	0.2577	0.4108	0.024*

	U11	U22	U33	U12	U13	U23
O4	0.0276 (6)	0.0393 (8)	0.0296 (6)	0.0024 (6)	0.0041 (4)	0.0055 (6)
O3	0.0216 (5)	0.0263 (6)	0.0200 (5)	0.0046 (5)	0.0061 (4)	0.0038 (5)
O5	0.0488 (7)	0.0514 (9)	0.0208 (6)	−0.0125 (7)	0.0030 (5)	−0.0045 (6)
O2	0.0145 (5)	0.0288 (7)	0.0290 (6)	0.0000 (5)	−0.0015 (4)	−0.0011 (5)
O1	0.0162 (5)	0.0249 (6)	0.0280 (5)	−0.0014 (5)	0.0051 (4)	0.0020 (5)
O4'	0.0290 (6)	0.0305 (7)	0.0233 (5)	−0.0010 (5)	0.0004 (4)	−0.0059 (5)
O3'	0.0184 (5)	0.0207 (6)	0.0247 (5)	0.0009 (5)	−0.0004 (4)	−0.0056 (5)
O5'	0.0194 (5)	0.0293 (7)	0.0272 (5)	0.0044 (5)	0.0025 (4)	0.0036 (5)
O2'	0.0146 (5)	0.0271 (6)	0.0322 (5)	0.0012 (5)	0.0031 (4)	0.0004 (5)
O1'	0.0176 (5)	0.0155 (6)	0.0296 (5)	0.0005 (4)	0.0043 (4)	−0.0030 (5)
N1	0.0135 (5)	0.0232 (7)	0.0204 (6)	0.0020 (6)	0.0018 (4)	−0.0001 (6)
N2'	0.0218 (6)	0.0180 (7)	0.0205 (6)	−0.0023 (6)	0.0027 (5)	0.0034 (5)
C8'	0.0214 (7)	0.0141 (8)	0.0205 (7)	−0.0017 (6)	0.0036 (6)	0.0026 (6)
N1'	0.0153 (6)	0.0176 (7)	0.0215 (6)	0.0003 (5)	−0.0026 (5)	−0.0014 (5)
N2	0.0366 (7)	0.0233 (8)	0.0206 (6)	0.0000 (7)	0.0035 (5)	0.0014 (6)
C11	0.0309 (8)	0.0168 (9)	0.0216 (7)	−0.0010 (7)	0.0046 (6)	−0.0016 (7)
C10	0.0246 (7)	0.0254 (9)	0.0229 (7)	0.0033 (7)	0.0010 (6)	−0.0015 (7)
C9	0.0272 (8)	0.0226 (9)	0.0192 (7)	0.0040 (7)	−0.0011 (6)	−0.0010 (7)
C8	0.0243 (7)	0.0162 (8)	0.0206 (7)	−0.0016 (7)	0.0000 (5)	−0.0024 (6)
C4	0.0184 (7)	0.0185 (9)	0.0238 (7)	0.0003 (6)	−0.0015 (5)	0.0004 (7)
C2	0.0170 (7)	0.0159 (8)	0.0217 (7)	0.0015 (6)	0.0007 (5)	0.0016 (6)
C1	0.0160 (6)	0.0182 (8)	0.0201 (7)	0.0005 (6)	0.0013 (5)	0.0007 (7)
C7A	0.0146 (6)	0.0179 (8)	0.0228 (7)	−0.0010 (6)	0.0003 (5)	0.0001 (6)
C7	0.0146 (6)	0.0249 (9)	0.0204 (7)	0.0008 (6)	0.0005 (5)	0.0005 (7)
C6	0.0190 (7)	0.0207 (8)	0.0194 (7)	0.0010 (7)	0.0018 (5)	−0.0003 (7)
C12	0.0326 (8)	0.0200 (9)	0.0195 (7)	−0.0045 (7)	−0.0043 (6)	0.0007 (7)
C13	0.0231 (7)	0.0187 (8)	0.0251 (7)	−0.0019 (7)	−0.0023 (6)	−0.0003 (7)
C5	0.0169 (7)	0.0283 (9)	0.0210 (7)	0.0003 (7)	0.0047 (5)	−0.0013 (7)
C3	0.0187 (7)	0.0145 (8)	0.0228 (7)	0.0034 (6)	−0.0004 (5)	0.0008 (6)
C11'	0.0200 (7)	0.0140 (8)	0.0214 (7)	−0.0016 (6)	0.0014 (5)	0.0032 (6)
C10'	0.0181 (6)	0.0151 (8)	0.0226 (7)	0.0013 (6)	0.0057 (5)	0.0012 (6)
C9'	0.0226 (7)	0.0166 (8)	0.0192 (7)	−0.0001 (6)	0.0048 (6)	0.0009 (6)
C4'	0.0176 (6)	0.0158 (8)	0.0248 (7)	−0.0009 (6)	0.0056 (6)	−0.0001 (6)
C2'	0.0164 (7)	0.0134 (8)	0.0239 (7)	0.0001 (6)	0.0012 (5)	−0.0005 (6)
C3'	0.0173 (7)	0.0147 (8)	0.0238 (7)	−0.0008 (6)	0.0002 (5)	−0.0035 (7)
C5'	0.0217 (7)	0.0198 (9)	0.0240 (7)	0.0001 (7)	−0.0054 (5)	−0.0009 (7)
C6'	0.0202 (7)	0.0197 (9)	0.0172 (6)	0.0013 (7)	0.0014 (5)	0.0003 (6)
C7'	0.0181 (6)	0.0197 (8)	0.0222 (7)	−0.0012 (7)	−0.0014 (5)	0.0009 (7)
C7A'	0.0150 (6)	0.0200 (9)	0.0179 (7)	0.0002 (6)	0.0008 (5)	−0.0025 (6)
C1'	0.0169 (7)	0.0149 (8)	0.0190 (6)	0.0007 (6)	0.0006 (5)	−0.0032 (6)
C13'	0.0191 (7)	0.0171 (8)	0.0240 (7)	0.0018 (6)	0.0080 (6)	0.0031 (7)
C12'	0.0233 (7)	0.0181 (8)	0.0182 (6)	−0.0003 (7)	0.0052 (6)	0.0004 (6)

O4—N2	1.2262 (18)	C1—C7A	1.5439 (19)
O3—C6	1.414 (2)	C1—H1	0.9800
O3—H3	0.8200	C7A—C7	1.518 (2)
O5—N2	1.2328 (18)	C7A—H7C	0.9800
O2—C3	1.2321 (19)	C7—C6	1.5374 (18)
O1—C1	1.4100 (19)	C7—H7A	0.9700
O1—H1A	0.8200	C7—H7B	0.9700
O4'—N2'	1.2266 (18)	C6—C5	1.5455 (19)
O3'—C6'	1.4316 (19)	C6—H6	0.9800
O3'—H3'	0.8200	C12—C13	1.389 (2)
O5'—N2'	1.2319 (17)	C12—H12	0.9300
O2'—C3'	1.2209 (18)	C13—H13	0.9300
O1'—C1'	1.434 (2)	C5—H5A	0.9700
O1'—H1A'	0.8200	C5—H5B	0.9700
N1—C3	1.3409 (19)	C11'—C12'	1.384 (2)
N1—C5	1.4608 (18)	C11'—C10'	1.391 (2)
N1—C7A	1.4637 (17)	C10'—C9'	1.383 (2)
N2'—C11'	1.4657 (19)	C10'—H10'	0.9300
C8'—C9'	1.400 (2)	C9'—H9'	0.9300
C8'—C13'	1.405 (2)	C4'—C2'	1.334 (2)
C8'—C4'	1.466 (2)	C4'—H4'	0.9300
N1'—C3'	1.3760 (19)	C2'—C3'	1.498 (2)
N1'—C5'	1.461 (2)	C2'—C1'	1.5073 (19)
N1'—C7A'	1.4696 (17)	C5'—C6'	1.549 (2)
N2—C11	1.4655 (19)	C5'—H5A'	0.9700
C11—C10	1.379 (2)	C5'—H5B'	0.9700
C11—C12	1.381 (2)	C6'—C7'	1.531 (2)
C10—C9	1.386 (2)	C6'—H6'	0.9800
C10—H10	0.9300	C7'—C7A'	1.526 (2)
C9—C8	1.402 (2)	C7'—H7A'	0.9700
C9—H9	0.9300	C7'—H7B'	0.9700
C8—C13	1.396 (2)	C7A'—C1'	1.537 (2)
C8—C4	1.467 (2)	C7A'—H7C'	0.9800
C4—C2	1.333 (2)	C1'—H1'	0.9800
C4—H4	0.9300	C13'—C12'	1.379 (2)
C2—C3	1.497 (2)	C13'—H13'	0.9300
C2—C1	1.5236 (19)	C12'—H12'	0.9300
C6—O3—H3	109.5	C12—C13—H13	119.2
C1—O1—H1A	109.5	C8—C13—H13	119.2
C6'—O3'—H3'	109.5	N1—C5—C6	102.60 (11)
C1'—O1'—H1A'	109.5	N1—C5—H5A	111.2
C3—N1—C5	129.22 (13)	C6—C5—H5A	111.2
C3—N1—C7A	114.76 (11)	N1—C5—H5B	111.2
C5—N1—C7A	113.38 (11)	C6—C5—H5B	111.2
O4'—N2'—O5'	123.76 (13)	H5A—C5—H5B	109.2
O4'—N2'—C11'	118.14 (12)	O2—C3—N1	125.74 (13)
O5'—N2'—C11'	118.08 (12)	O2—C3—C2	127.10 (13)
C9'—C8'—C13'	118.70 (13)	N1—C3—C2	107.10 (12)
C9'—C8'—C4'	124.39 (13)	C12'—C11'—C10'	122.56 (14)
C13'—C8'—C4'	116.89 (13)	C12'—C11'—N2'	118.47 (13)
C3'—N1'—C5'	121.79 (13)	C10'—C11'—N2'	118.92 (13)
C3'—N1'—C7A'	111.93 (11)	C9'—C10'—C11'	118.88 (13)
C5'—N1'—C7A'	109.02 (12)	C9'—C10'—H10'	120.6
O4—N2—O5	123.54 (13)	C11'—C10'—H10'	120.6
O4—N2—C11	118.90 (12)	C10'—C9'—C8'	120.32 (14)
O5—N2—C11	117.55 (13)	C10'—C9'—H9'	119.8
C10—C11—C12	122.37 (14)	C8'—C9'—H9'	119.8
C10—C11—N2	119.32 (14)	C2'—C4'—C8'	129.29 (14)
C12—C11—N2	118.31 (13)	C2'—C4'—H4'	115.4
C11—C10—C9	119.04 (15)	C8'—C4'—H4'	115.4
C11—C10—H10	120.5	C4'—C2'—C3'	119.78 (13)
C9—C10—H10	120.5	C4'—C2'—C1'	131.40 (13)
C10—C9—C8	120.56 (14)	C3'—C2'—C1'	108.31 (12)
C10—C9—H9	119.7	O2'—C3'—N1'	125.71 (13)
C8—C9—H9	119.7	O2'—C3'—C2'	127.20 (13)
C13—C8—C9	118.40 (14)	N1'—C3'—C2'	107.07 (12)
C13—C8—C4	117.06 (13)	N1'—C5'—C6'	104.55 (11)
C9—C8—C4	124.50 (13)	N1'—C5'—H5A'	110.8
C2—C4—C8	131.99 (14)	C6'—C5'—H5A'	110.8
C2—C4—H4	114.0	N1'—C5'—H5B'	110.8
C8—C4—H4	114.0	C6'—C5'—H5B'	110.8
C4—C2—C3	118.93 (13)	H5A'—C5'—H5B'	108.9
C4—C2—C1	133.59 (13)	O3'—C6'—C7'	107.72 (12)
C3—C2—C1	107.43 (11)	O3'—C6'—C5'	112.42 (12)
O1—C1—C2	114.00 (12)	C7'—C6'—C5'	105.71 (13)
O1—C1—C7A	111.46 (13)	O3'—C6'—H6'	110.3
C2—C1—C7A	102.77 (11)	C7'—C6'—H6'	110.3
O1—C1—H1	109.5	C5'—C6'—H6'	110.3
C2—C1—H1	109.5	C7A'—C7'—C6'	105.95 (12)
C7A—C1—H1	109.5	C7A'—C7'—H7A'	110.5
N1—C7A—C7	102.11 (11)	C6'—C7'—H7A'	110.5
N1—C7A—C1	103.90 (11)	C7A'—C7'—H7B'	110.5
C7—C7A—C1	121.27 (13)	C6'—C7'—H7B'	110.5
N1—C7A—H7C	109.6	H7A'—C7'—H7B'	108.7
C7—C7A—H7C	109.6	N1'—C7A'—C7'	103.06 (12)
C1—C7A—H7C	109.6	N1'—C7A'—C1'	104.75 (11)
C7A—C7—C6	102.61 (11)	C7'—C7A'—C1'	117.14 (12)
C7A—C7—H7A	111.2	N1'—C7A'—H7C'	110.5
C6—C7—H7A	111.2	C7'—C7A'—H7C'	110.5
C7A—C7—H7B	111.2	C1'—C7A'—H7C'	110.5
C6—C7—H7B	111.2	O1'—C1'—C2'	111.62 (12)
H7A—C7—H7B	109.2	O1'—C1'—C7A'	112.18 (11)
O3—C6—C5	113.29 (13)	C2'—C1'—C7A'	102.81 (11)
O3—C6—C7	110.09 (12)	O1'—C1'—H1'	110.0
C5—C6—C7	103.96 (11)	C2'—C1'—H1'	110.0
O3—C6—H6	109.8	C7A'—C1'—H1'	110.0
C5—C6—H6	109.8	C12'—C13'—C8'	121.81 (13)
C7—C6—H6	109.8	C12'—C13'—H13'	119.1
C11—C12—C13	117.93 (14)	C8'—C13'—H13'	119.1
C11—C12—H12	121.0	C13'—C12'—C11'	117.65 (13)
C13—C12—H12	121.0	C13'—C12'—H12'	121.2
C12—C13—C8	121.61 (14)	C11'—C12'—H12'	121.2
O4—N2—C11—C10	26.1 (2)	O4'—N2'—C11'—C12'	11.0 (2)
O5—N2—C11—C10	−154.96 (17)	O5'—N2'—C11'—C12'	−170.61 (15)
O4—N2—C11—C12	−153.41 (17)	O4'—N2'—C11'—C10'	−166.52 (15)
O5—N2—C11—C12	25.5 (2)	O5'—N2'—C11'—C10'	11.9 (2)
C12—C11—C10—C9	1.3 (3)	C12'—C11'—C10'—C9'	−2.3 (2)
N2—C11—C10—C9	−178.18 (16)	N2'—C11'—C10'—C9'	175.13 (14)
C11—C10—C9—C8	1.6 (3)	C11'—C10'—C9'—C8'	0.7 (2)
C10—C9—C8—C13	−3.3 (3)	C13'—C8'—C9'—C10'	1.8 (2)
C10—C9—C8—C4	179.20 (16)	C4'—C8'—C9'—C10'	−176.78 (15)
C13—C8—C4—C2	165.53 (19)	C9'—C8'—C4'—C2'	20.8 (3)
C9—C8—C4—C2	−16.9 (3)	C13'—C8'—C4'—C2'	−157.82 (17)
C8—C4—C2—C3	177.05 (17)	C8'—C4'—C2'—C3'	170.07 (16)
C8—C4—C2—C1	0.0 (3)	C8'—C4'—C2'—C1'	−0.8 (3)
C4—C2—C1—O1	−43.3 (3)	C5'—N1'—C3'—O2'	−36.3 (2)
C3—C2—C1—O1	139.45 (13)	C7A'—N1'—C3'—O2'	−167.84 (16)
C4—C2—C1—C7A	−164.06 (19)	C5'—N1'—C3'—C2'	141.93 (13)
C3—C2—C1—C7A	18.68 (16)	C7A'—N1'—C3'—C2'	10.41 (17)
C3—N1—C7A—C7	140.96 (14)	C4'—C2'—C3'—O2'	10.2 (3)
C5—N1—C7A—C7	−22.39 (18)	C1'—C2'—C3'—O2'	−177.00 (16)
C3—N1—C7A—C1	14.10 (18)	C4'—C2'—C3'—N1'	−168.00 (15)
C5—N1—C7A—C1	−149.25 (14)	C1'—C2'—C3'—N1'	4.77 (17)
O1—C1—C7A—N1	−141.64 (12)	C3'—N1'—C5'—C6'	−103.79 (15)
C2—C1—C7A—N1	−19.14 (16)	C7A'—N1'—C5'—C6'	28.93 (15)
O1—C1—C7A—C7	104.60 (16)	N1'—C5'—C6'—O3'	107.05 (14)
C2—C1—C7A—C7	−132.91 (14)	N1'—C5'—C6'—C7'	−10.21 (15)
N1—C7A—C7—C6	36.32 (15)	O3'—C6'—C7'—C7A'	−131.16 (13)
C1—C7A—C7—C6	151.00 (14)	C5'—C6'—C7'—C7A'	−10.78 (15)
C7A—C7—C6—O3	−159.78 (13)	C3'—N1'—C7A'—C7'	102.01 (14)
C7A—C7—C6—C5	−38.13 (16)	C5'—N1'—C7A'—C7'	−35.68 (14)
C10—C11—C12—C13	−2.3 (3)	C3'—N1'—C7A'—C1'	−21.04 (17)
N2—C11—C12—C13	177.18 (16)	C5'—N1'—C7A'—C1'	−158.73 (12)
C11—C12—C13—C8	0.5 (3)	C6'—C7'—C7A'—N1'	27.53 (14)
C9—C8—C13—C12	2.2 (3)	C6'—C7'—C7A'—C1'	141.91 (12)
C4—C8—C13—C12	179.95 (16)	C4'—C2'—C1'—O1'	−84.7 (2)
C3—N1—C5—C6	−161.69 (16)	C3'—C2'—C1'—O1'	103.71 (14)
C7A—N1—C5—C6	−1.32 (18)	C4'—C2'—C1'—C7A'	154.90 (17)
O3—C6—C5—N1	143.86 (13)	C3'—C2'—C1'—C7A'	−16.73 (15)
C7—C6—C5—N1	24.36 (16)	N1'—C7A'—C1'—O1'	−97.99 (13)
C5—N1—C3—O2	−19.5 (3)	C7'—C7A'—C1'—O1'	148.58 (12)
C7A—N1—C3—O2	−179.69 (15)	N1'—C7A'—C1'—C2'	22.06 (15)
C5—N1—C3—C2	157.98 (16)	C7'—C7A'—C1'—C2'	−91.37 (14)
C7A—N1—C3—C2	−2.17 (18)	C9'—C8'—C13'—C12'	−3.0 (2)
C4—C2—C3—O2	−11.3 (3)	C4'—C8'—C13'—C12'	175.74 (15)
C1—C2—C3—O2	166.43 (16)	C8'—C13'—C12'—C11'	1.5 (2)
C4—C2—C3—N1	171.22 (16)	C10'—C11'—C12'—C13'	1.2 (2)
C1—C2—C3—N1	−11.05 (17)	N2'—C11'—C12'—C13'	−176.23 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1′i	0.82	1.93	2.7303 (14)	166
O1—H1A···O2ii	0.82	1.89	2.6993 (15)	169
O3′—H3′···O3iii	0.82	1.95	2.7585 (15)	171
O1′—H1A′···O3′iv	0.82	1.93	2.7451 (15)	174
C1′—H1′···O2′ii	0.98	2.52	3.3655 (17)	144
C1′—H1′···O5′v	0.98	2.55	3.3242 (19)	136
C10—H10···O1vi	0.93	2.54	3.126 (2)	121
C12′—H12′···O3′vii	0.93	2.57	3.5014 (18)	174
C13—H13···O4i	0.93	2.51	3.2644 (19)	138
C13′—H13′···O5′i	0.93	2.51	3.1160 (18)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1′i	0.82	1.93	2.7303 (14)	166
O1—H1A⋯O2ii	0.82	1.89	2.6993 (15)	169
O3′—H3′⋯O3iii	0.82	1.95	2.7585 (15)	171
O1′—H1A′⋯O3′iv	0.82	1.93	2.7451 (15)	174
C1′—H1′⋯O2′ii	0.98	2.52	3.3655 (17)	144
C1′—H1′⋯O5′v	0.98	2.55	3.3242 (19)	136
C10—H10⋯O1vi	0.93	2.54	3.126 (2)	121
C12′—H12′⋯O3′vii	0.93	2.57	3.5014 (18)	174
C13—H13⋯O4i	0.93	2.51	3.2644 (19)	138
C13′—H13′⋯O5′i	0.93	2.51	3.1160 (18)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .