Crystal structure of bis-(allyl-ammonium) oxalate.

The title salt, 2C3H8N(+)·C2O4 (2-), crystallized with six independent allyl-ammonium cations and three independent oxalate dianions in the asymmetric unit. One of the oxalate dianions is nearly planar [dihedral angle between CO2 planes = 1.91 (19)°], while the other two are twisted with angles of 11.3 (3) and 26.09 (13)°. One cation has a synperiplanar (cis) conformation with an N-C-C-C torsion angle of 0.9 (3)°, whereas the five remaining cations are characterized by gauche arrangements, with the N-C-C-C torsion angles ranging from 115.9 (12) to 128.8 (3)°. One of the allyl-ammonium cations is positionally disordered (fixed occupancy ratio = 0.45:0.55). In the crystal, the cations and anions are connected by a number of strong N-H⋯O and N-H⋯(O,O) hydrogen bonds, forming layers parallel to (001), with the vinyl groups protruding into the space between the layers.

Related literature

For the crystal structures of oxalic acid salts with aliphatic amines, see: Dziuk et al. (2014a ▶,b ▶); Braga et al. (2013 ▶); Ejsmont & Zaleski (2006a ▶,b ▶); Ejsmont (2006 ▶, 2007 ▶). For the crystal structures of salts with disordered allyl­ammonium cations, see: Płowaś et al. (2010 ▶); Zarychta et al. (2007 ▶).

Experimental

Crystal data

2C3H8N+·C2O4 −

M = 204.23

Monoclinic,

a = 6.7060 (3) Å

b = 12.1364 (10) Å

c = 40.6017 (16) Å

β = 93.969 (4)°

V = 3296.5 (3) Å3

Z = 12

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.25 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

21821 measured reflections

6460 independent reflections

4306 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.132

S = 1.03

6460 reflections

397 parameters

38 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814023617/su5011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023617/su5011Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023617/su5011Isup3.cml

Click here for additional data file.

B B . DOI: 10.1107/S1600536814023617/su5011fig1.tif

The mol­ecular structure of the asymmetric unit of the title salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. One of the allyl­ammonium cations is positionally disorded and only the major components, atoms C17B and C18B, are shown for clarity.

Click here for additional data file.

b . DOI: 10.1107/S1600536814023617/su5011fig2.tif

The crystal packing viewed along the b axis of the title salt. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1031212

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C3H8N+·C2O4−	F(000) = 1320
Mr = 204.23	Dx = 1.235 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7060 (3) Å	Cell parameters from 21821 reflections
b = 12.1364 (10) Å	θ = 3.0–26.0°
c = 40.6017 (16) Å	µ = 0.10 mm−1
β = 93.969 (4)°	T = 100 K
V = 3296.5 (3) Å3	Block, colourless
Z = 12	0.25 × 0.15 × 0.10 mm

Oxford Diffraction Xcalibur CCD diffractometer	4306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 26.0°, θmin = 3.0°
ω scan	h = −8→8
21821 measured reflections	k = −14→13
6460 independent reflections	l = −49→47

Refinement on F2	38 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6460 reflections	Δρmax = 0.57 e Å−3
397 parameters	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.0693 (2)	0.39719 (14)	0.24556 (4)	0.0168 (4)
H1A	0.1840	0.3626	0.2509	0.025*
H1B	−0.0319	0.3503	0.2469	0.025*
H1C	0.0549	0.4530	0.2594	0.025*
C1	0.0706 (3)	0.43979 (19)	0.21148 (5)	0.0233 (5)
H1D	0.0888	0.3789	0.1965	0.028*
H1E	0.1825	0.4898	0.2101	0.028*
C2	−0.1179 (4)	0.4984 (2)	0.20118 (6)	0.0286 (6)
H2D	−0.2376	0.4615	0.2035	0.034*
C3	−0.1275 (4)	0.5981 (2)	0.18910 (7)	0.0423 (7)
H3D	−0.0108	0.6375	0.1864	0.051*
H3E	−0.2511	0.6297	0.1832	0.051*
N2	0.9169 (2)	0.04985 (13)	0.07308 (4)	0.0146 (4)
H2A	1.0339	0.0818	0.0786	0.022*
H2B	0.8945	−0.0030	0.0876	0.022*
H2C	0.8199	0.0999	0.0731	0.022*
C4	0.9211 (3)	0.00129 (18)	0.03964 (5)	0.0197 (5)
H4D	1.0297	−0.0514	0.0395	0.024*
H4E	0.9463	0.0591	0.0239	0.024*
C5	0.7292 (3)	−0.0550 (2)	0.02916 (6)	0.0247 (5)
H5D	0.6114	−0.0148	0.0298	0.030*
C6	0.7165 (4)	−0.1577 (2)	0.01908 (6)	0.0354 (7)
H6D	0.8317	−0.1999	0.0182	0.042*
H6E	0.5923	−0.1882	0.0129	0.042*
N3	0.7745 (2)	0.40896 (13)	0.05764 (4)	0.0159 (4)
H3A	0.7731	0.4511	0.0756	0.024*
H3B	0.8881	0.3709	0.0582	0.024*
H3C	0.6716	0.3625	0.0571	0.024*
C7	0.7589 (3)	0.47910 (18)	0.02790 (6)	0.0262 (6)
H7A	0.8698	0.5306	0.0290	0.031*
H7B	0.6364	0.5216	0.0278	0.031*
C8	0.7597 (3)	0.4167 (2)	−0.00353 (6)	0.0303 (6)
H8A	0.7520	0.4582	−0.0228	0.036*
C9	0.7701 (4)	0.3098 (2)	−0.00713 (6)	0.0319 (6)
H9A	0.7781	0.2642	0.0113	0.038*
H9B	0.7694	0.2793	−0.0282	0.038*
N4	1.2953 (2)	0.54981 (14)	0.09731 (4)	0.0173 (4)
H4A	1.1841	0.5880	0.0923	0.026*
H4B	1.3041	0.4947	0.0830	0.026*
H4C	1.4009	0.5939	0.0963	0.026*
C10	1.2902 (4)	0.5047 (2)	0.13118 (6)	0.0285 (6)
H10A	1.2791	0.5650	0.1466	0.034*
H10B	1.1728	0.4585	0.1323	0.034*
C11	1.4686 (4)	0.4398 (2)	0.14102 (6)	0.0382 (7)
H11A	1.5926	0.4719	0.1385	0.046*
C12	1.4659 (5)	0.3402 (3)	0.15312 (7)	0.0548 (9)
H12A	1.3446	0.3057	0.1560	0.066*
H12B	1.5854	0.3038	0.1588	0.066*
N5	0.4296 (2)	0.89624 (14)	0.10655 (4)	0.0174 (4)
H5A	0.3922	0.9540	0.0941	0.026*
H5B	0.3529	0.8386	0.1007	0.026*
H5C	0.5567	0.8801	0.1037	0.026*
C13	0.4079 (4)	0.92265 (19)	0.14159 (6)	0.0270 (6)
H13A	0.4922	0.9853	0.1478	0.032*
H13B	0.2705	0.9436	0.1443	0.032*
C14	0.4622 (5)	0.8297 (2)	0.16383 (7)	0.0433 (7)
H14A	0.5926	0.8043	0.1630	0.052*
C15	0.3600 (5)	0.7797 (2)	0.18369 (7)	0.0518 (9)
H15A	0.2281	0.8004	0.1859	0.062*
H15B	0.4159	0.7219	0.1962	0.062*
N6	0.9227 (2)	0.05348 (14)	0.22058 (4)	0.0177 (4)
H6A	0.9646	−0.0048	0.2325	0.027*
H6B	0.7959	0.0677	0.2243	0.027*
H6C	0.9981	0.1116	0.2264	0.027*
C16	0.9382 (4)	0.0301 (2)	0.18525 (6)	0.0298 (6)
H16A	1.0365	−0.0278	0.1833	0.036*
H16B	0.8106	0.0016	0.1763	0.036*
C17A	0.9923 (12)	0.1216 (5)	0.16504 (16)	0.0347 (15)	0.45
H17A	1.1199	0.1483	0.1709	0.042*	0.45
C18A	0.9094 (14)	0.1719 (13)	0.1421 (4)	0.038 (3)	0.45
H18A	0.7810	0.1521	0.1342	0.045*	0.45
H18B	0.9745	0.2300	0.1325	0.045*	0.45
C17B	0.8712 (8)	0.1232 (4)	0.16450 (13)	0.0240 (11)	0.55
H17B	0.7410	0.1482	0.1660	0.029*	0.55
C18B	0.9883 (12)	0.1764 (10)	0.1429 (3)	0.033 (2)	0.55
H18C	1.1192	0.1534	0.1408	0.040*	0.55
H18D	0.9364	0.2352	0.1303	0.040*	0.55
O1	0.8657 (2)	0.86307 (11)	0.11197 (4)	0.0174 (3)
O2	1.1046 (2)	0.76253 (12)	0.09007 (4)	0.0212 (4)
O3	0.6117 (2)	0.69093 (12)	0.09661 (4)	0.0297 (4)
O4	0.8778 (2)	0.58025 (11)	0.09925 (4)	0.0239 (4)
C19	0.9343 (3)	0.77562 (17)	0.10068 (5)	0.0143 (5)
C20	0.7955 (3)	0.67310 (17)	0.09876 (5)	0.0162 (5)
O5	0.3551 (2)	0.37126 (11)	0.05668 (3)	0.0159 (3)
O6	0.0928 (2)	0.26559 (12)	0.06678 (4)	0.0222 (4)
O7	0.5985 (2)	0.19598 (11)	0.06801 (4)	0.0191 (4)
O8	0.3342 (2)	0.09181 (11)	0.07784 (4)	0.0219 (4)
C21	0.2742 (3)	0.28163 (16)	0.06386 (5)	0.0122 (4)
C22	0.4160 (3)	0.18068 (16)	0.07032 (5)	0.0139 (5)
O9	0.7477 (2)	0.25409 (12)	0.23883 (4)	0.0237 (4)
O10	0.4852 (2)	0.35506 (12)	0.25117 (4)	0.0257 (4)
O11	0.4942 (2)	0.08883 (11)	0.21818 (4)	0.0173 (3)
O12	0.2475 (2)	0.18011 (12)	0.24079 (4)	0.0226 (4)
C23	0.5651 (3)	0.26894 (17)	0.24167 (5)	0.0159 (5)
C24	0.4224 (3)	0.17033 (16)	0.23246 (5)	0.0145 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0115 (9)	0.0126 (9)	0.0267 (11)	0.0018 (7)	0.0032 (8)	−0.0010 (8)
C1	0.0230 (13)	0.0245 (13)	0.0229 (13)	0.0013 (10)	0.0052 (10)	−0.0006 (10)
C2	0.0228 (13)	0.0355 (15)	0.0271 (14)	−0.0015 (11)	−0.0021 (11)	0.0036 (12)
C3	0.0470 (18)	0.0395 (17)	0.0396 (17)	0.0115 (14)	−0.0023 (14)	0.0070 (14)
N2	0.0111 (9)	0.0115 (9)	0.0215 (10)	−0.0007 (7)	0.0030 (7)	0.0005 (8)
C4	0.0203 (12)	0.0191 (12)	0.0203 (13)	0.0009 (9)	0.0057 (9)	−0.0006 (9)
C5	0.0182 (12)	0.0328 (14)	0.0228 (13)	0.0016 (10)	0.0006 (10)	−0.0030 (11)
C6	0.0305 (15)	0.0404 (17)	0.0354 (16)	−0.0147 (12)	0.0043 (12)	−0.0091 (13)
N3	0.0099 (9)	0.0121 (9)	0.0258 (11)	0.0013 (7)	0.0019 (7)	0.0002 (8)
C7	0.0200 (13)	0.0198 (12)	0.0389 (15)	0.0038 (10)	0.0029 (11)	0.0156 (11)
C8	0.0174 (13)	0.0453 (17)	0.0284 (15)	0.0011 (11)	0.0036 (10)	0.0180 (12)
C9	0.0280 (15)	0.0460 (17)	0.0215 (14)	0.0002 (12)	0.0008 (11)	0.0024 (12)
N4	0.0132 (9)	0.0116 (9)	0.0271 (11)	0.0004 (7)	0.0028 (8)	−0.0016 (8)
C10	0.0341 (15)	0.0277 (14)	0.0243 (14)	0.0049 (11)	0.0064 (11)	−0.0018 (11)
C11	0.0286 (15)	0.0543 (19)	0.0316 (16)	0.0057 (13)	0.0012 (11)	0.0025 (14)
C12	0.051 (2)	0.051 (2)	0.063 (2)	0.0295 (16)	0.0130 (16)	0.0173 (17)
N5	0.0120 (9)	0.0124 (9)	0.0284 (11)	0.0037 (7)	0.0052 (8)	0.0034 (8)
C13	0.0320 (14)	0.0199 (13)	0.0291 (14)	0.0025 (10)	0.0023 (11)	−0.0026 (11)
C14	0.071 (2)	0.0266 (15)	0.0324 (16)	0.0002 (14)	0.0049 (15)	−0.0014 (13)
C15	0.089 (3)	0.0298 (16)	0.0397 (18)	0.0032 (16)	0.0267 (17)	−0.0064 (14)
N6	0.0115 (9)	0.0122 (9)	0.0298 (11)	0.0018 (7)	0.0038 (8)	0.0012 (8)
C16	0.0402 (16)	0.0240 (14)	0.0251 (14)	0.0026 (11)	0.0022 (11)	−0.0071 (11)
C17A	0.044 (4)	0.034 (3)	0.027 (3)	−0.002 (3)	0.007 (3)	−0.004 (3)
C18A	0.035 (6)	0.041 (5)	0.038 (4)	0.004 (6)	0.010 (6)	−0.003 (4)
C17B	0.020 (3)	0.025 (2)	0.026 (3)	0.002 (2)	0.001 (2)	0.002 (2)
C18B	0.044 (5)	0.027 (3)	0.030 (4)	−0.010 (5)	0.014 (5)	−0.003 (3)
O1	0.0182 (8)	0.0107 (8)	0.0238 (9)	0.0014 (6)	0.0054 (7)	−0.0017 (6)
O2	0.0151 (8)	0.0170 (8)	0.0322 (9)	−0.0004 (6)	0.0075 (7)	−0.0012 (7)
O3	0.0121 (9)	0.0157 (8)	0.0617 (13)	0.0009 (6)	0.0045 (8)	−0.0035 (8)
O4	0.0193 (8)	0.0096 (8)	0.0430 (11)	0.0015 (6)	0.0030 (7)	−0.0033 (7)
C19	0.0149 (11)	0.0124 (11)	0.0155 (11)	0.0007 (9)	0.0006 (9)	0.0017 (9)
C20	0.0163 (12)	0.0142 (11)	0.0187 (12)	−0.0004 (9)	0.0054 (9)	−0.0032 (9)
O5	0.0149 (8)	0.0095 (7)	0.0236 (9)	−0.0001 (6)	0.0045 (6)	0.0020 (6)
O6	0.0112 (8)	0.0159 (8)	0.0401 (10)	0.0028 (6)	0.0049 (7)	0.0070 (7)
O7	0.0100 (8)	0.0136 (8)	0.0340 (10)	0.0015 (6)	0.0036 (6)	0.0030 (7)
O8	0.0120 (8)	0.0114 (8)	0.0425 (10)	0.0013 (6)	0.0026 (7)	0.0098 (7)
C21	0.0117 (11)	0.0111 (10)	0.0141 (11)	0.0016 (8)	0.0019 (8)	−0.0007 (8)
C22	0.0120 (11)	0.0133 (11)	0.0165 (11)	−0.0002 (9)	0.0022 (8)	0.0005 (9)
O9	0.0123 (8)	0.0156 (8)	0.0436 (11)	−0.0008 (6)	0.0054 (7)	−0.0042 (7)
O10	0.0167 (9)	0.0126 (8)	0.0479 (11)	0.0013 (6)	0.0039 (7)	−0.0110 (7)
O11	0.0171 (8)	0.0126 (8)	0.0227 (9)	0.0005 (6)	0.0041 (6)	−0.0034 (6)
O12	0.0118 (8)	0.0193 (8)	0.0376 (10)	−0.0019 (6)	0.0072 (7)	−0.0065 (7)
C23	0.0142 (11)	0.0118 (11)	0.0217 (12)	0.0005 (9)	0.0013 (9)	0.0008 (9)
C24	0.0145 (12)	0.0103 (11)	0.0188 (12)	0.0010 (9)	0.0025 (9)	0.0026 (9)

N1—C1	1.478 (3)	C12—H12B	0.9300
N1—H1A	0.8900	N5—C13	1.475 (3)
N1—H1B	0.8900	N5—H5A	0.8900
N1—H1C	0.8900	N5—H5B	0.8900
C1—C2	1.485 (3)	N5—H5C	0.8900
C1—H1D	0.9700	C13—C14	1.475 (3)
C1—H1E	0.9700	C13—H13A	0.9700
C2—C3	1.305 (3)	C13—H13B	0.9700
C2—H2D	0.9300	C14—C15	1.251 (4)
C3—H3D	0.9300	C14—H14A	0.9300
C3—H3E	0.9300	C15—H15A	0.9300
N2—C4	1.482 (3)	C15—H15B	0.9300
N2—H2A	0.8900	N6—C16	1.473 (3)
N2—H2B	0.8900	N6—H6A	0.8900
N2—H2C	0.8900	N6—H6B	0.8900
C4—C5	1.492 (3)	N6—H6C	0.8900
C4—H4D	0.9700	C16—C17A	1.442 (7)
C4—H4E	0.9700	C16—C17B	1.461 (6)
C5—C6	1.313 (3)	C16—H16A	0.9700
C5—H5D	0.9300	C16—H16B	0.9700
C6—H6D	0.9300	C17A—C18A	1.215 (17)
C6—H6E	0.9300	C17A—H17A	0.9300
N3—C7	1.475 (3)	C18A—H18A	0.9300
N3—H3A	0.8900	C18A—H18B	0.9300
N3—H3B	0.8900	C17B—C18B	1.379 (11)
N3—H3C	0.8900	C17B—H17B	0.9300
C7—C8	1.484 (3)	C18B—H18C	0.9300
C7—H7A	0.9700	C18B—H18D	0.9300
C7—H7B	0.9700	O1—C19	1.256 (2)
C8—C9	1.308 (3)	O2—C19	1.259 (2)
C8—H8A	0.9300	O3—C20	1.249 (2)
C9—H9A	0.9300	O4—C20	1.254 (2)
C9—H9B	0.9300	C19—C20	1.552 (3)
N4—C10	1.483 (3)	O5—C21	1.259 (2)
N4—H4A	0.8900	O6—C21	1.246 (2)
N4—H4B	0.8900	O7—C22	1.247 (2)
N4—H4C	0.8900	O8—C22	1.257 (2)
C10—C11	1.464 (3)	C21—C22	1.562 (3)
C10—H10A	0.9700	O9—C23	1.251 (2)
C10—H10B	0.9700	O10—C23	1.248 (2)
C11—C12	1.305 (4)	O11—C24	1.259 (2)
C11—H11A	0.9300	O12—C24	1.249 (2)
C12—H12A	0.9300	C23—C24	1.562 (3)
C1—N1—H1A	109.5	C12—C11—H11A	117.7
C1—N1—H1B	109.5	C10—C11—H11A	117.7
H1A—N1—H1B	109.5	C11—C12—H12A	120.0
C1—N1—H1C	109.5	C11—C12—H12B	120.0
H1A—N1—H1C	109.5	H12A—C12—H12B	120.0
H1B—N1—H1C	109.5	C13—N5—H5A	109.5
N1—C1—C2	111.78 (18)	C13—N5—H5B	109.5
N1—C1—H1D	109.3	H5A—N5—H5B	109.5
C2—C1—H1D	109.3	C13—N5—H5C	109.5
N1—C1—H1E	109.3	H5A—N5—H5C	109.5
C2—C1—H1E	109.3	H5B—N5—H5C	109.5
H1D—C1—H1E	107.9	C14—C13—N5	112.82 (19)
C3—C2—C1	124.7 (2)	C14—C13—H13A	109.0
C3—C2—H2D	117.7	N5—C13—H13A	109.0
C1—C2—H2D	117.7	C14—C13—H13B	109.0
C2—C3—H3D	120.0	N5—C13—H13B	109.0
C2—C3—H3E	120.0	H13A—C13—H13B	107.8
H3D—C3—H3E	120.0	C15—C14—C13	130.0 (3)
C4—N2—H2A	109.5	C15—C14—H14A	115.0
C4—N2—H2B	109.5	C13—C14—H14A	115.0
H2A—N2—H2B	109.5	C14—C15—H15A	120.0
C4—N2—H2C	109.5	C14—C15—H15B	120.0
H2A—N2—H2C	109.5	H15A—C15—H15B	120.0
H2B—N2—H2C	109.5	C16—N6—H6A	109.5
N2—C4—C5	111.87 (17)	C16—N6—H6B	109.5
N2—C4—H4D	109.2	H6A—N6—H6B	109.5
C5—C4—H4D	109.2	C16—N6—H6C	109.5
N2—C4—H4E	109.2	H6A—N6—H6C	109.5
C5—C4—H4E	109.2	H6B—N6—H6C	109.5
H4D—C4—H4E	107.9	C17A—C16—N6	116.3 (3)
C6—C5—C4	124.0 (2)	C17B—C16—N6	111.9 (3)
C6—C5—H5D	118.0	C17A—C16—H16A	108.2
C4—C5—H5D	118.0	N6—C16—H16A	108.2
C5—C6—H6D	120.0	C17A—C16—H16B	108.2
C5—C6—H6E	120.0	N6—C16—H16B	108.2
H6D—C6—H6E	120.0	H16A—C16—H16B	107.4
C7—N3—H3A	109.5	C18A—C17A—C16	134.7 (9)
C7—N3—H3B	109.5	C18A—C17A—H17A	112.7
H3A—N3—H3B	109.5	C16—C17A—H17A	112.7
C7—N3—H3C	109.5	C17A—C18A—H18A	120.0
H3A—N3—H3C	109.5	C17A—C18A—H18B	120.0
H3B—N3—H3C	109.5	H18A—C18A—H18B	120.0
N3—C7—C8	113.89 (19)	C18B—C17B—C16	124.3 (6)
N3—C7—H7A	108.8	C18B—C17B—H17B	117.9
C8—C7—H7A	108.8	C16—C17B—H17B	117.9
N3—C7—H7B	108.8	C17B—C18B—H18C	120.0
C8—C7—H7B	108.8	C17B—C18B—H18D	120.0
H7A—C7—H7B	107.7	H18C—C18B—H18D	120.0
C9—C8—C7	127.3 (2)	O1—C19—O2	126.54 (19)
C9—C8—H8A	116.4	O1—C19—C20	117.53 (18)
C7—C8—H8A	116.4	O2—C19—C20	115.91 (18)
C8—C9—H9A	120.0	O3—C20—O4	126.0 (2)
C8—C9—H9B	120.0	O3—C20—C19	116.75 (18)
H9A—C9—H9B	120.0	O4—C20—C19	117.23 (18)
C10—N4—H4A	109.5	O6—C21—O5	126.61 (19)
C10—N4—H4B	109.5	O6—C21—C22	116.67 (17)
H4A—N4—H4B	109.5	O5—C21—C22	116.71 (17)
C10—N4—H4C	109.5	O7—C22—O8	126.35 (19)
H4A—N4—H4C	109.5	O7—C22—C21	117.36 (17)
H4B—N4—H4C	109.5	O8—C22—C21	116.28 (18)
C11—C10—N4	112.4 (2)	O10—C23—O9	126.4 (2)
C11—C10—H10A	109.1	O10—C23—C24	116.53 (18)
N4—C10—H10A	109.1	O9—C23—C24	117.08 (18)
C11—C10—H10B	109.1	O12—C24—O11	126.59 (19)
N4—C10—H10B	109.1	O12—C24—C23	115.73 (18)
H10A—C10—H10B	107.9	O11—C24—C23	117.67 (18)
C12—C11—C10	124.6 (3)
N1—C1—C2—C3	127.2 (3)	O1—C19—C20—O4	−154.87 (19)
N2—C4—C5—C6	−125.8 (2)	O2—C19—C20—O4	26.3 (3)
N3—C7—C8—C9	0.9 (3)	O6—C21—C22—O7	−178.86 (18)
N4—C10—C11—C12	−128.8 (3)	O5—C21—C22—O7	0.2 (3)
N5—C13—C14—C15	−120.8 (3)	O6—C21—C22—O8	0.2 (3)
C17B—C16—C17A—C18A	−26.1 (11)	O5—C21—C22—O8	179.22 (19)
N6—C16—C17A—C18A	−115.9 (12)	O10—C23—C24—O12	−11.9 (3)
C17A—C16—C17B—C18B	16.7 (7)	O9—C23—C24—O12	168.12 (19)
N6—C16—C17B—C18B	121.6 (7)	O10—C23—C24—O11	169.54 (19)
O1—C19—C20—O3	25.7 (3)	O9—C23—C24—O11	−10.5 (3)
O2—C19—C20—O3	−153.11 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O10	0.89	2.02	2.829 (2)	150
N1—H1A···O12	0.89	2.30	2.905 (2)	125
N1—H1B···O9i	0.89	1.89	2.768 (2)	167
N1—H1C···O11ii	0.89	1.92	2.801 (2)	169
N2—H2A···O6iii	0.89	2.32	2.890 (2)	122
N2—H2A···O8iii	0.89	2.02	2.838 (2)	152
N2—H2B···O1iv	0.89	1.92	2.797 (2)	168
N2—H2C···O7	0.89	1.89	2.773 (2)	172
N3—H3A···O4	0.89	1.94	2.737 (2)	148
N3—H3B···O6iii	0.89	1.89	2.759 (2)	165
N3—H3C···O5	0.89	2.12	2.847 (2)	138
N3—H3C···O7	0.89	2.13	2.885 (2)	142
N4—H4A···O2	0.89	2.18	2.887 (2)	135
N4—H4A···O4	0.89	2.10	2.831 (2)	139
N4—H4B···O5iii	0.89	1.89	2.769 (2)	172
N4—H4C···O3iii	0.89	1.84	2.728 (2)	176
N5—H5A···O8v	0.89	1.83	2.701 (2)	165
N5—H5B···O2i	0.89	1.93	2.762 (2)	156
N5—H5C···O1	0.89	2.09	2.945 (2)	162
N6—H6A···O10vi	0.89	1.85	2.720 (2)	166
N6—H6B···O11	0.89	2.04	2.900 (2)	163
N6—H6C···O12iii	0.89	1.92	2.744 (2)	153

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO10	0.89	2.02	2.829(2)	150
N1H1AO12	0.89	2.30	2.905(2)	125
N1H1BO9i	0.89	1.89	2.768(2)	167
N1H1CO11ii	0.89	1.92	2.801(2)	169
N2H2AO6iii	0.89	2.32	2.890(2)	122
N2H2AO8iii	0.89	2.02	2.838(2)	152
N2H2BO1iv	0.89	1.92	2.797(2)	168
N2H2CO7	0.89	1.89	2.773(2)	172
N3H3AO4	0.89	1.94	2.737(2)	148
N3H3BO6iii	0.89	1.89	2.759(2)	165
N3H3CO5	0.89	2.12	2.847(2)	138
N3H3CO7	0.89	2.13	2.885(2)	142
N4H4AO2	0.89	2.18	2.887(2)	135
N4H4AO4	0.89	2.10	2.831(2)	139
N4H4BO5iii	0.89	1.89	2.769(2)	172
N4H4CO3iii	0.89	1.84	2.728(2)	176
N5H5AO8v	0.89	1.83	2.701(2)	165
N5H5BO2i	0.89	1.93	2.762(2)	156
N5H5CO1	0.89	2.09	2.945(2)	162
N6H6AO10vi	0.89	1.85	2.720(2)	166
N6H6BO11	0.89	2.04	2.900(2)	163
N6H6CO12iii	0.89	1.92	2.744(2)	153

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