Tedisamil sesquifumarate

In the title compound, bis­[3,7-bis­(cyclo­propyl­methyl)-7-aza-3-azonia­spiro­[bi­cyclo­[3.3.1]­nonane-9,1′-cyclo­pentane]] (2E)-but-2-enedionate bis­[(2E)-but-2-enedioic acid], 2C₁₉H₃₃N₂⁺·C₄H₂O₄²⁻·2C₄H₄O₄, the cations are protonated at only one N atom and there is no evidence of any disorder involving the alternative nitro­gen. The system N⁺—H...N represents an intramolecular hydrogen bond. The fumarate and fumaric acid residues form a network of 50-membered rings by classical hydrogen bonding; the cations are linked to these by C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.166
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.136
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  O1      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B   ..  O1      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O2      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B   ..  O5      ..       2.63 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11

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

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

bis[3,7-bis(cyclopropylmethyl)-7-aza-3-azoniaspiro[bicyclo[3.3.1]nonane-9,1'- cyclopentane]] (2E)-but-2-enedionate bis[(2E)-but-2-enedioic acid]

Crystal data

2C19H33N2^+·C4H2O4^2^−·2C4H4O4	F(000) = 1000
Mr = 925.15	Dx = 1.263 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6692 (15) Å	Cell parameters from 4119 reflections
b = 17.257 (2) Å	θ = 2.2–30.0°
c = 13.3990 (18) Å	µ = 0.09 mm^−1
β = 99.70 (2)°	T = 153 K
V = 2431.8 (6) Å^3	Prism, colourless
Z = 2	0.40 × 0.28 × 0.27 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.136
Graphite monochromator	θmax = 26.4°, θmin = 1.9°
Detector resolution: 8.192 pixels mm^-1	h = −10→13
ω scans	k = −20→21
15020 measured reflections	l = −15→16
4981 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.089P)^2] where P = (Fo^2 + 2Fc^2)/3
4981 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.6553 (0.0099) x - 8.7761 (0.0195) y + 1.9805 (0.0213) z = 2.1321 (0.0132)

* -0.0198 (0.0014) C9 * 0.0206 (0.0015) C2' * -0.0137 (0.0010) C3' * 0.0129 (0.0009) C5' 0.6278 (0.0040) C4'

Rms deviation of fitted atoms = 0.0171

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
C1	0.35772 (18)	0.11651 (11)	0.61692 (14)	0.0234 (4)
H1	0.4024	0.0728	0.6572	0.028*
C8	0.36827 (18)	0.10367 (12)	0.50560 (14)	0.0247 (4)
H8A	0.4590	0.1020	0.4981	0.030*
H8B	0.3291	0.0534	0.4824	0.030*
N7	0.30293 (15)	0.16735 (10)	0.44239 (11)	0.0236 (4)
C6	0.16856 (18)	0.17370 (13)	0.45523 (14)	0.0280 (5)
H6A	0.1224	0.1262	0.4288	0.034*
H6B	0.1288	0.2183	0.4155	0.034*
C5	0.15652 (19)	0.18457 (12)	0.56705 (14)	0.0275 (5)
H5	0.0641	0.1869	0.5721	0.033*
C4	0.21858 (18)	0.26044 (12)	0.60754 (15)	0.0273 (5)
H4A	0.1757	0.3043	0.5682	0.033*
H4B	0.2084	0.2672	0.6791	0.033*
N3	0.35747 (15)	0.26084 (9)	0.60017 (12)	0.0232 (4)
H03	0.362 (2)	0.2541 (14)	0.5353 (17)	0.035 (6)*
C2	0.42444 (18)	0.19231 (12)	0.65512 (14)	0.0245 (4)
H2A	0.4246	0.1977	0.7287	0.029*
H2B	0.5139	0.1910	0.6441	0.029*
C9	0.21703 (19)	0.11596 (12)	0.63193 (14)	0.0262 (5)
C2'	0.1494 (2)	0.03711 (14)	0.59840 (17)	0.0368 (5)
H2'A	0.0813	0.0453	0.5394	0.044*
H2'B	0.2115	−0.0003	0.5790	0.044*
C3'	0.0940 (3)	0.00624 (16)	0.68649 (18)	0.0506 (7)
H3'A	0.0959	−0.0511	0.6880	0.061*
H3'B	0.0052	0.0240	0.6837	0.061*
C5'	0.2014 (2)	0.12235 (13)	0.74524 (15)	0.0320 (5)
H5'A	0.2784	0.1452	0.7862	0.038*
H5'B	0.1272	0.1551	0.7523	0.038*
C4'	0.1817 (3)	0.04045 (15)	0.77877 (18)	0.0473 (6)
H4'A	0.1405	0.0396	0.8397	0.057*
H4'B	0.2632	0.0119	0.7933	0.057*
C10'	0.31035 (19)	0.15774 (12)	0.33425 (14)	0.0276 (5)
H10C	0.2566	0.1978	0.2952	0.033*
H10D	0.2744	0.1066	0.3116	0.033*
C11'	0.4420 (2)	0.16332 (12)	0.30956 (14)	0.0287 (5)
H11'	0.4899	0.2117	0.3324	0.034*
C12'	0.5211 (2)	0.09183 (14)	0.30533 (16)	0.0351 (5)
H12C	0.6142	0.0964	0.3267	0.042*
H12D	0.4844	0.0416	0.3216	0.042*
C13'	0.4624 (2)	0.13151 (15)	0.20962 (15)	0.0366 (5)
H13C	0.3897	0.1057	0.1668	0.044*
H13D	0.5195	0.1606	0.1719	0.044*
C10	0.4205 (2)	0.33667 (13)	0.63367 (15)	0.0335 (5)
H10A	0.3654	0.3798	0.6038	0.040*
H10B	0.4300	0.3408	0.7083	0.040*
C11	0.5478 (2)	0.34437 (12)	0.60311 (15)	0.0319 (5)
H11	0.6162	0.3099	0.6389	0.038*
C12	0.5887 (2)	0.42340 (14)	0.57532 (19)	0.0421 (6)
H12A	0.5286	0.4669	0.5772	0.050*
H12B	0.6796	0.4372	0.5948	0.050*
C13	0.5543 (2)	0.36278 (15)	0.49550 (18)	0.0415 (6)
H13A	0.4731	0.3690	0.4481	0.050*
H13B	0.6241	0.3393	0.4656	0.050*
C14	0.32376 (17)	0.28376 (12)	−0.04895 (14)	0.0258 (4)
C15	0.27210 (19)	0.33457 (12)	0.02459 (15)	0.0272 (4)
H15	0.2172	0.3756	−0.0021	0.033*
C16	0.29699 (18)	0.32676 (12)	0.12383 (14)	0.0261 (4)
H16	0.3496	0.2853	0.1526	0.031*
C17	0.24376 (18)	0.38203 (12)	0.19196 (15)	0.0267 (5)
O1	0.32191 (16)	0.30298 (9)	−0.13644 (10)	0.0389 (4)
O2	0.37336 (14)	0.21865 (9)	−0.00873 (10)	0.0303 (4)
H02	0.429 (3)	0.1930 (17)	−0.051 (2)	0.060 (8)*
O3	0.17613 (16)	0.43585 (9)	0.16025 (12)	0.0420 (4)
O4	0.27529 (14)	0.36312 (10)	0.28825 (11)	0.0351 (4)
H04	0.225 (3)	0.395 (2)	0.327 (2)	0.084 (10)*
C18	0.56201 (18)	0.08283 (11)	−0.07715 (13)	0.0233 (4)
C19	0.48188 (18)	0.03384 (11)	−0.02018 (13)	0.0232 (4)
H19	0.4003	0.0527	−0.0128	0.028*
O5	0.66722 (14)	0.05652 (9)	−0.09153 (11)	0.0354 (4)
O6	0.51953 (13)	0.14893 (8)	−0.10649 (10)	0.0270 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0230 (10)	0.0234 (10)	0.0223 (9)	0.0015 (8)	−0.0004 (8)	0.0033 (8)
C8	0.0242 (10)	0.0256 (11)	0.0231 (10)	0.0032 (8)	0.0003 (8)	0.0013 (8)
N7	0.0218 (8)	0.0278 (9)	0.0195 (8)	0.0033 (7)	−0.0013 (6)	0.0008 (7)
C6	0.0207 (10)	0.0340 (12)	0.0274 (10)	0.0026 (9)	−0.0018 (8)	0.0019 (9)
C5	0.0182 (10)	0.0346 (12)	0.0288 (10)	0.0014 (8)	0.0011 (8)	0.0013 (9)
C4	0.0221 (10)	0.0322 (12)	0.0280 (10)	0.0081 (9)	0.0052 (8)	0.0010 (8)
N3	0.0244 (9)	0.0235 (9)	0.0212 (8)	0.0011 (7)	0.0026 (7)	−0.0009 (7)
C2	0.0208 (10)	0.0285 (11)	0.0224 (9)	0.0005 (8)	−0.0013 (8)	0.0025 (8)
C9	0.0245 (10)	0.0293 (11)	0.0239 (10)	−0.0049 (8)	0.0012 (8)	−0.0024 (8)
C2'	0.0354 (12)	0.0384 (14)	0.0344 (12)	−0.0138 (10)	0.0002 (10)	−0.0023 (10)
C3'	0.0631 (17)	0.0417 (15)	0.0491 (15)	−0.0210 (13)	0.0153 (13)	−0.0032 (12)
C5'	0.0295 (11)	0.0369 (13)	0.0303 (11)	−0.0065 (9)	0.0069 (9)	−0.0013 (9)
C4'	0.0674 (18)	0.0397 (15)	0.0360 (13)	−0.0042 (13)	0.0128 (12)	0.0042 (11)
C10'	0.0287 (11)	0.0323 (12)	0.0197 (10)	0.0023 (9)	−0.0017 (8)	0.0008 (8)
C11'	0.0301 (11)	0.0288 (11)	0.0264 (10)	−0.0047 (9)	0.0026 (9)	−0.0010 (9)
C12'	0.0285 (11)	0.0406 (13)	0.0361 (12)	0.0006 (10)	0.0051 (9)	−0.0025 (10)
C13'	0.0332 (12)	0.0512 (15)	0.0257 (11)	−0.0078 (11)	0.0054 (9)	−0.0027 (10)
C10	0.0450 (13)	0.0268 (12)	0.0287 (11)	−0.0064 (10)	0.0067 (10)	−0.0060 (9)
C11	0.0283 (11)	0.0266 (12)	0.0361 (12)	−0.0052 (9)	−0.0083 (9)	0.0049 (9)
C12	0.0345 (13)	0.0324 (13)	0.0551 (15)	−0.0073 (10)	−0.0044 (11)	0.0107 (11)
C13	0.0360 (13)	0.0463 (15)	0.0439 (13)	−0.0007 (11)	0.0117 (11)	0.0056 (11)
C14	0.0211 (10)	0.0284 (11)	0.0263 (10)	−0.0030 (8)	−0.0003 (8)	−0.0007 (8)
C15	0.0246 (10)	0.0247 (11)	0.0308 (10)	0.0002 (8)	0.0004 (8)	0.0016 (8)
C16	0.0218 (10)	0.0261 (11)	0.0302 (11)	0.0013 (8)	0.0034 (8)	0.0011 (8)
C17	0.0224 (10)	0.0257 (11)	0.0315 (11)	−0.0031 (8)	0.0030 (8)	−0.0016 (8)
O1	0.0529 (10)	0.0389 (9)	0.0249 (8)	0.0104 (8)	0.0069 (7)	0.0043 (6)
O2	0.0369 (8)	0.0276 (8)	0.0266 (7)	0.0076 (7)	0.0064 (6)	0.0019 (6)
O3	0.0475 (10)	0.0377 (10)	0.0396 (9)	0.0186 (8)	0.0042 (7)	0.0001 (7)
O4	0.0372 (9)	0.0417 (9)	0.0267 (8)	0.0108 (7)	0.0064 (7)	−0.0022 (7)
C18	0.0273 (11)	0.0228 (10)	0.0190 (9)	0.0021 (8)	0.0011 (8)	0.0003 (8)
C19	0.0224 (10)	0.0271 (10)	0.0199 (9)	0.0015 (8)	0.0028 (8)	0.0007 (7)
O5	0.0301 (8)	0.0362 (9)	0.0427 (9)	0.0089 (7)	0.0147 (7)	0.0141 (7)
O6	0.0291 (8)	0.0238 (8)	0.0282 (7)	0.0029 (6)	0.0049 (6)	0.0040 (6)

Geometric parameters (Å, º)

N3—C4	1.502 (2)	C10'—H10C	0.9900
N3—C10	1.505 (3)	C10'—H10D	0.9900
N3—C2	1.508 (2)	C11'—C13'	1.497 (3)
N7—C8	1.487 (2)	C11'—C12'	1.501 (3)
N7—C10'	1.474 (2)	C11'—H11'	1.0000
N7—C6	1.476 (2)	C12'—C13'	1.495 (3)
C1—C8	1.531 (3)	C12'—H12C	0.9900
C1—C2	1.535 (3)	C12'—H12D	0.9900
C1—C9	1.548 (3)	C13'—H13C	0.9900
C1—H1	1.0000	C13'—H13D	0.9900
C8—H8A	0.9900	C10—C11	1.489 (3)
C8—H8B	0.9900	C10—H10A	0.9900
C6—C5	1.537 (3)	C10—H10B	0.9900
C6—H6A	0.9900	C11—C13	1.490 (3)
C6—H6B	0.9900	C11—C12	1.498 (3)
C5—C4	1.525 (3)	C11—H11	1.0000
C5—C9	1.544 (3)	C12—C13	1.497 (4)
C5—H5	1.0000	C12—H12A	0.9900
C4—H4A	0.9900	C12—H12B	0.9900
C4—H4B	0.9900	C13—H13A	0.9900
N3—H03	0.89 (2)	C13—H13B	0.9900
C2—H2A	0.9900	C14—O1	1.215 (2)
C2—H2B	0.9900	C14—O2	1.318 (2)
C9—C5'	1.559 (3)	C14—C15	1.492 (3)
C9—C2'	1.570 (3)	C15—C16	1.318 (3)
C2'—C3'	1.504 (3)	C15—H15	0.9500
C2'—H2'A	0.9900	C16—C17	1.497 (3)
C2'—H2'B	0.9900	C16—H16	0.9500
C3'—C4'	1.537 (3)	C17—O3	1.208 (2)
C3'—H3'A	0.9900	C17—O4	1.318 (2)
C3'—H3'B	0.9900	O2—H02	0.99 (3)
C5'—C4'	1.508 (3)	O4—H04	0.98 (3)
C5'—H5'A	0.9900	C18—O5	1.255 (2)
C5'—H5'B	0.9900	C18—O6	1.265 (2)
C4'—H4'A	0.9900	C18—C19	1.499 (3)
C4'—H4'B	0.9900	C19—C19^i	1.317 (4)
C10'—C11'	1.499 (3)	C19—H19	0.9500
C4—N3—C10	112.38 (15)	C5'—C4'—H4'B	111.3
C4—N3—C2	110.85 (15)	C3'—C4'—H4'B	111.3
C10—N3—C2	112.65 (15)	H4'A—C4'—H4'B	109.2
C10'—N7—C6	109.69 (15)	N7—C10'—C11'	114.65 (16)
C10'—N7—C8	112.28 (15)	N7—C10'—H10C	108.6
C6—N7—C8	111.08 (15)	C11'—C10'—H10C	108.6
C8—C1—C2	110.01 (16)	N7—C10'—H10D	108.6
C8—C1—C9	110.97 (16)	C11'—C10'—H10D	108.6
C2—C1—C9	111.54 (16)	H10C—C10'—H10D	107.6
C8—C1—H1	108.1	C13'—C11'—C10'	117.19 (18)
C2—C1—H1	108.1	C13'—C11'—C12'	59.81 (15)
C9—C1—H1	108.1	C10'—C11'—C12'	120.59 (18)
N7—C8—C1	110.10 (15)	C13'—C11'—H11'	115.9
N7—C8—H8A	109.6	C10'—C11'—H11'	115.9
C1—C8—H8A	109.6	C12'—C11'—H11'	115.9
N7—C8—H8B	109.6	C13'—C12'—C11'	59.95 (14)
C1—C8—H8B	109.6	C13'—C12'—H12C	117.8
H8A—C8—H8B	108.2	C11'—C12'—H12C	117.8
N7—C6—C5	111.41 (16)	C13'—C12'—H12D	117.8
N7—C6—H6A	109.3	C11'—C12'—H12D	117.8
C5—C6—H6A	109.3	H12C—C12'—H12D	114.9
N7—C6—H6B	109.3	C12'—C13'—C11'	60.24 (14)
C5—C6—H6B	109.3	C12'—C13'—H13C	117.7
H6A—C6—H6B	108.0	C11'—C13'—H13C	117.7
C4—C5—C6	110.43 (16)	C12'—C13'—H13D	117.7
C4—C5—C9	110.04 (16)	C11'—C13'—H13D	117.7
C6—C5—C9	111.07 (16)	H13C—C13'—H13D	114.9
C4—C5—H5	108.4	C11—C10—N3	112.21 (17)
C6—C5—H5	108.4	C11—C10—H10A	109.2
C9—C5—H5	108.4	N3—C10—H10A	109.2
N3—C4—C5	110.78 (15)	C11—C10—H10B	109.2
N3—C4—H4A	109.5	N3—C10—H10B	109.2
C5—C4—H4A	109.5	H10A—C10—H10B	107.9
N3—C4—H4B	109.5	C10—C11—C13	118.62 (19)
C5—C4—H4B	109.5	C10—C11—C12	117.8 (2)
H4A—C4—H4B	108.1	C13—C11—C12	60.13 (16)
C4—N3—H03	106.0 (15)	C10—C11—H11	116.2
C10—N3—H03	108.3 (15)	C13—C11—H11	116.2
C2—N3—H03	106.2 (15)	C12—C11—H11	116.2
N3—C2—C1	110.51 (15)	C13—C12—C11	59.66 (15)
N3—C2—H2A	109.5	C13—C12—H12A	117.8
C1—C2—H2A	109.5	C11—C12—H12A	117.8
N3—C2—H2B	109.5	C13—C12—H12B	117.8
C1—C2—H2B	109.5	C11—C12—H12B	117.8
H2A—C2—H2B	108.1	H12A—C12—H12B	114.9
C5—C9—C1	104.16 (15)	C11—C13—C12	60.21 (15)
C5—C9—C5'	113.00 (17)	C11—C13—H13A	117.8
C1—C9—C5'	113.05 (16)	C12—C13—H13A	117.8
C5—C9—C2'	112.03 (17)	C11—C13—H13B	117.8
C1—C9—C2'	112.15 (17)	C12—C13—H13B	117.7
C5'—C9—C2'	102.74 (16)	H13A—C13—H13B	114.9
C3'—C2'—C9	107.76 (18)	O1—C14—O2	124.56 (19)
C3'—C2'—H2'A	110.2	O1—C14—C15	121.92 (19)
C9—C2'—H2'A	110.2	O2—C14—C15	113.49 (16)
C3'—C2'—H2'B	110.2	C16—C15—C14	124.88 (19)
C9—C2'—H2'B	110.2	C16—C15—H15	117.6
H2'A—C2'—H2'B	108.5	C14—C15—H15	117.6
C2'—C3'—C4'	103.21 (19)	C15—C16—C17	121.15 (19)
C2'—C3'—H3'A	111.1	C15—C16—H16	119.4
C4'—C3'—H3'A	111.1	C17—C16—H16	119.4
C2'—C3'—H3'B	111.1	O3—C17—O4	124.97 (19)
C4'—C3'—H3'B	111.1	O3—C17—C16	122.74 (18)
H3'A—C3'—H3'B	109.1	O4—C17—C16	112.24 (18)
C4'—C5'—C9	105.48 (18)	C14—O2—H02	112.8 (16)
C4'—C5'—H5'A	110.6	C17—O4—H04	108 (2)
C9—C5'—H5'A	110.6	O5—C18—O6	124.13 (18)
C4'—C5'—H5'B	110.6	O5—C18—C19	118.39 (17)
C9—C5'—H5'B	110.6	O6—C18—C19	117.47 (16)
H5'A—C5'—H5'B	108.8	C19^i—C19—C18	123.8 (2)
C5'—C4'—C3'	102.52 (19)	C19^i—C19—H19	118.1
C5'—C4'—H4'A	111.3	C18—C19—H19	118.1
C3'—C4'—H4'A	111.3
C2—C1—C8—N7	−62.3 (2)	C5—C9—C2'—C3'	−118.2 (2)
C9—C1—C8—N7	61.7 (2)	C1—C9—C2'—C3'	125.1 (2)
C1—C8—N7—C10'	179.98 (16)	C5'—C9—C2'—C3'	3.4 (2)
C1—C8—N7—C6	−56.8 (2)	C9—C2'—C3'—C4'	−27.7 (3)
C10'—N7—C6—C5	−179.47 (16)	C5—C9—C5'—C4'	143.8 (2)
C8—N7—C6—C5	55.8 (2)	C1—C9—C5'—C4'	−98.2 (2)
N7—C6—C5—C4	63.1 (2)	C2'—C9—C5'—C4'	22.9 (2)
N7—C6—C5—C9	−59.2 (2)	C9—C5'—C4'—C3'	−40.3 (2)
C6—C5—C4—N3	−60.4 (2)	C2'—C3'—C4'—C5'	41.8 (3)
C9—C5—C4—N3	62.6 (2)	C6—N7—C10'—C11'	170.70 (17)
C5—C4—N3—C10	176.60 (16)	C8—N7—C10'—C11'	−65.3 (2)
C5—C4—N3—C2	−56.3 (2)	N7—C10'—C11'—C13'	162.33 (18)
C4—N3—C2—C1	54.04 (19)	N7—C10'—C11'—C12'	93.0 (2)
C10—N3—C2—C1	−179.06 (15)	C10'—C11'—C12'—C13'	105.7 (2)
C8—C1—C2—N3	64.74 (19)	C10'—C11'—C13'—C12'	−111.3 (2)
C9—C1—C2—N3	−58.9 (2)	C4—N3—C10—C11	−165.95 (17)
C4—C5—C9—C1	−62.87 (19)	C2—N3—C10—C11	68.0 (2)
C6—C5—C9—C1	59.7 (2)	N3—C10—C11—C13	76.3 (2)
C4—C5—C9—C5'	60.2 (2)	N3—C10—C11—C12	145.58 (19)
C6—C5—C9—C5'	−177.19 (16)	C10—C11—C12—C13	−108.8 (2)
C4—C5—C9—C2'	175.69 (16)	C10—C11—C13—C12	107.5 (2)
C6—C5—C9—C2'	−61.7 (2)	O1—C14—C15—C16	−163.1 (2)
C8—C1—C9—C5	−61.45 (19)	O2—C14—C15—C16	15.1 (3)
C2—C1—C9—C5	61.60 (19)	C14—C15—C16—C17	178.19 (18)
C8—C1—C9—C5'	175.50 (17)	C15—C16—C17—O3	0.1 (3)
C2—C1—C9—C5'	−61.5 (2)	C15—C16—C17—O4	177.66 (19)
C8—C1—C9—C2'	59.9 (2)	O5—C18—C19—C19^i	3.5 (3)
C2—C1—C9—C2'	−177.05 (16)	O6—C18—C19—C19^i	−175.5 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H03···N7	0.89 (2)	1.98 (2)	2.645 (2)	131 (2)
O2—H02···O6	0.99 (3)	1.52 (3)	2.5067 (19)	175 (3)
O4—H04···O5^ii	0.98 (3)	1.58 (3)	2.544 (2)	168 (3)
C12′—H12D···O3^iii	0.99	2.54	3.495 (3)	161
C6—H6B···O6^ii	0.99	2.57	3.484 (3)	154
C2—H2A···O6^iv	0.99	2.42	3.271 (2)	144
C4—H4B···O1^iv	0.99	2.64	3.500 (2)	146
C10—H10B···O1^iv	0.99	2.63	3.468 (3)	143
C5—H5···O2^ii	1.00	2.69	3.452 (3)	133
C12—H12B···O5^v	0.99	2.63	3.452 (3)	140

Symmetry codes: (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x, y, z+1; (v) −x+3/2, y+1/2, −z+1/2.