9-Amino-acridin-10-ium 4-amino-benzo-ate dihydrate.

The asymmetric unit of the title hydrated salt, C13H11N2 (+)·C7H6NO2 (-)·2H2O, consists of two independent 9-amino-acridinium cations, two 4-amino-benzoate anions and four water mol-ecules. Both 9-amino-acridinium cations are essentially planar, with maximum deviations of 0.034 (1) and 0.025 (2) Å, and are protonated at the pyridine N atoms. The 4-amino-benzoate anions are approximately planar, with dihedral angles of 9.16 (19) and 5.4 (2)° between the benzene ring and the carboxyl-ate group. In the crystal, the two independent anions are connected by N-H⋯O hydrogen bonds, forming a layer parallel to (100). The layers are connected through the cations by N-H⋯N and N-H⋯O hydrogen bonds. The water mol-ecules, which form O-H⋯O hydrogen-bonded chains along the b-axis direction, connect the anions and the cations by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. The crystal structure also features π-π inter-actions [centroid-centroid distances = 3.6343 (9)-3.8366 (10) Å] and a C-H⋯π inter-action.

Related literature

For background to and the biological activity of acridine derivatives, see: Shubber et al. (1986 ▶); Sondhi et al. (2006 ▶); Salamanca & Khalil (2005 ▶). For related structures, see: Aghabozorg et al. (2010 ▶); Mei & Wolf (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H11N2 +·C7H6NO2 −·2H2O

M = 367.40

Monoclinic,

a = 25.6891 (9) Å

b = 7.2800 (2) Å

c = 21.6485 (6) Å

β = 114.865 (1)°

V = 3673.32 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.64 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.990

39382 measured reflections

10114 independent reflections

7214 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.128

S = 1.04

10114 reflections

559 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.25 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401023X/is5353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401023X/is5353Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401023X/is5353Isup3.cml

CCDC reference: 1001221

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

C13H11N2+·C7H6NO2−·2H2O	F(000) = 1552
Mr = 367.40	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9979 reflections
a = 25.6891 (9) Å	θ = 2.6–30.0°
b = 7.2800 (2) Å	µ = 0.09 mm−1
c = 21.6485 (6) Å	T = 100 K
β = 114.865 (1)°	Needle, yellow
V = 3673.32 (19) Å3	0.64 × 0.14 × 0.11 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	10114 independent reflections
Radiation source: fine-focus sealed tube	7214 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 29.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −34→35
Tmin = 0.942, Tmax = 0.990	k = −10→10
39382 measured reflections	l = −29→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0477P)2 + 1.9401P] where P = (Fo2 + 2Fc2)/3
10114 reflections	(Δ/σ)max = 0.001
559 parameters	Δρmax = 0.53 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A	0.86360 (5)	0.58428 (18)	0.11715 (7)	0.0268 (3)
O2A	0.87227 (5)	0.88589 (17)	0.10751 (6)	0.0222 (3)
N1A	0.67465 (6)	0.8427 (2)	0.21685 (8)	0.0242 (3)
N2A	0.05332 (5)	0.2784 (2)	0.45535 (7)	0.0180 (3)
N3A	−0.04990 (6)	0.2128 (2)	0.55740 (7)	0.0199 (3)
C1A	0.72048 (6)	0.8241 (2)	0.19910 (8)	0.0199 (3)
C2A	0.74005 (7)	0.9733 (3)	0.17409 (9)	0.0235 (4)
H2AA	0.7243	1.0919	0.1732	0.028*
C3A	0.78230 (7)	0.9496 (3)	0.15049 (9)	0.0222 (4)
H3AA	0.7954	1.0529	0.1342	0.027*
C4A	0.80575 (6)	0.7776 (2)	0.15040 (8)	0.0182 (3)
C5A	0.78674 (6)	0.6297 (2)	0.17669 (8)	0.0193 (3)
H5AA	0.8025	0.5112	0.1776	0.023*
C6A	0.74549 (6)	0.6517 (2)	0.20143 (8)	0.0195 (3)
H6AA	0.7341	0.5495	0.2201	0.023*
C7A	0.85012 (6)	0.7471 (2)	0.12315 (8)	0.0193 (3)
C8A	0.07687 (6)	0.2119 (2)	0.52023 (8)	0.0169 (3)
C9A	0.13552 (7)	0.1634 (2)	0.55063 (9)	0.0214 (3)
H9AA	0.1579	0.1734	0.5253	0.026*
C10A	0.16021 (7)	0.1021 (3)	0.61654 (9)	0.0239 (4)
H10A	0.1998	0.0717	0.6368	0.029*
C11A	0.12751 (7)	0.0835 (3)	0.65452 (9)	0.0226 (4)
H11A	0.1452	0.0425	0.7004	0.027*
C12A	0.07030 (7)	0.1245 (2)	0.62534 (8)	0.0193 (3)
H12A	0.0483	0.1091	0.6509	0.023*
C13A	0.04320 (6)	0.1901 (2)	0.55725 (8)	0.0162 (3)
C14A	−0.01692 (6)	0.2343 (2)	0.52463 (8)	0.0166 (3)
C15A	−0.04016 (6)	0.3026 (2)	0.45590 (8)	0.0167 (3)
C16A	−0.09877 (6)	0.3509 (2)	0.41950 (8)	0.0195 (3)
H16A	−0.1242	0.3381	0.4409	0.023*
C17A	−0.11937 (7)	0.4155 (2)	0.35427 (8)	0.0217 (3)
H17A	−0.1587	0.4480	0.3308	0.026*
C18A	−0.08208 (7)	0.4338 (3)	0.32192 (8)	0.0229 (4)
H18A	−0.0966	0.4777	0.2764	0.028*
C19A	−0.02525 (7)	0.3891 (2)	0.35517 (8)	0.0208 (3)
H19A	−0.0005	0.4028	0.3329	0.025*
C20A	−0.00344 (6)	0.3226 (2)	0.42261 (8)	0.0171 (3)
O1B	0.37845 (5)	0.68571 (17)	0.26050 (6)	0.0230 (3)
O2B	0.36397 (5)	0.98772 (18)	0.25207 (6)	0.0261 (3)
N1B	0.17296 (6)	0.7568 (2)	−0.03882 (8)	0.0229 (3)
N2B	0.54393 (6)	0.2571 (2)	0.59970 (7)	0.0202 (3)
N3B	0.44631 (6)	0.2602 (2)	0.39185 (7)	0.0220 (3)
C1B	0.21918 (6)	0.7727 (2)	0.02383 (8)	0.0194 (3)
C2B	0.23209 (7)	0.9435 (3)	0.05693 (9)	0.0245 (4)
H2BA	0.2112	1.0494	0.0343	0.029*
C3B	0.27492 (7)	0.9592 (3)	0.12218 (9)	0.0239 (4)
H3BA	0.2830	1.0761	0.1437	0.029*
C4B	0.30656 (6)	0.8068 (2)	0.15708 (8)	0.0190 (3)
C5B	0.29449 (6)	0.6376 (2)	0.12345 (8)	0.0190 (3)
H5BA	0.3158	0.5321	0.1460	0.023*
C6B	0.25205 (7)	0.6210 (2)	0.05779 (9)	0.0203 (3)
H6BA	0.2452	0.5051	0.0356	0.024*
C7B	0.35265 (6)	0.8283 (2)	0.22785 (8)	0.0197 (3)
C8B	0.48841 (7)	0.3151 (2)	0.57499 (8)	0.0198 (3)
C9B	0.46617 (7)	0.3731 (3)	0.62140 (9)	0.0239 (4)
H9BA	0.4899	0.3729	0.6689	0.029*
C10B	0.41040 (7)	0.4296 (3)	0.59768 (9)	0.0260 (4)
H10B	0.3956	0.4675	0.6291	0.031*
C11B	0.37436 (7)	0.4325 (3)	0.52712 (9)	0.0227 (4)
H11B	0.3356	0.4720	0.5113	0.027*
C12B	0.39578 (7)	0.3779 (2)	0.48192 (9)	0.0225 (4)
H12B	0.3716	0.3808	0.4345	0.027*
C13B	0.45352 (6)	0.3169 (2)	0.50437 (8)	0.0193 (3)
C14B	0.47737 (6)	0.2568 (2)	0.45815 (8)	0.0173 (3)
C15B	0.53592 (6)	0.1946 (2)	0.48670 (8)	0.0161 (3)
C16B	0.56309 (7)	0.1301 (2)	0.44572 (8)	0.0204 (3)
H16B	0.5422	0.1278	0.3976	0.025*
C17B	0.61859 (7)	0.0714 (3)	0.47412 (9)	0.0238 (4)
H17B	0.6360	0.0285	0.4459	0.029*
C18B	0.64998 (7)	0.0744 (3)	0.54509 (9)	0.0246 (4)
H18B	0.6888	0.0344	0.5646	0.030*
C19B	0.62536 (7)	0.1343 (2)	0.58664 (9)	0.0225 (4)
H19B	0.6468	0.1340	0.6347	0.027*
C20B	0.56781 (6)	0.1966 (2)	0.55777 (8)	0.0176 (3)
O1W	0.43871 (6)	0.4726 (2)	0.20699 (7)	0.0283 (3)
O2W	0.06211 (6)	0.5855 (2)	0.27425 (7)	0.0285 (3)
O3W	0.46498 (6)	0.14630 (19)	0.27833 (6)	0.0279 (3)
O4W	0.96560 (6)	0.42092 (19)	0.18638 (7)	0.0246 (3)
H1NA	0.6681 (9)	0.745 (3)	0.2392 (11)	0.034 (6)*
H2NA	0.6685 (9)	0.956 (4)	0.2310 (11)	0.043 (7)*
H3NA	0.0766 (9)	0.302 (3)	0.4345 (10)	0.033 (5)*
H4NA	−0.0364 (9)	0.170 (3)	0.6019 (11)	0.037 (6)*
H5NA	−0.0885 (9)	0.234 (3)	0.5365 (10)	0.030 (5)*
H1NB	0.1604 (9)	0.851 (3)	−0.0650 (11)	0.035 (6)*
H2NB	0.1705 (9)	0.659 (3)	−0.0644 (11)	0.038 (6)*
H3NB	0.5628 (10)	0.266 (3)	0.6495 (12)	0.051 (7)*
H4NB	0.4051 (10)	0.296 (3)	0.3709 (11)	0.044 (6)*
H5NB	0.4588 (9)	0.224 (3)	0.3608 (9)	0.041 (6)*
H1W1	0.4462 (11)	0.373 (4)	0.2282 (13)	0.053 (8)*
H2W1	0.4187 (11)	0.536 (4)	0.2230 (13)	0.055 (8)*
H1W2	0.0841 (11)	0.525 (4)	0.3115 (14)	0.060 (8)*
H2W2	0.0538 (11)	0.692 (4)	0.2861 (13)	0.055 (8)*
H1W3	0.4345 (12)	0.077 (4)	0.2731 (14)	0.073 (9)*
H2W3	0.4977 (11)	0.079 (4)	0.2807 (12)	0.052 (7)*
H1W4	0.9960 (10)	0.486 (4)	0.2157 (12)	0.048 (7)*
H2W4	0.9360 (11)	0.492 (4)	0.1677 (12)	0.050 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0245 (6)	0.0221 (7)	0.0370 (7)	0.0003 (5)	0.0161 (5)	−0.0081 (6)
O2A	0.0229 (5)	0.0225 (7)	0.0252 (6)	−0.0014 (5)	0.0140 (5)	−0.0016 (5)
N1A	0.0249 (7)	0.0214 (9)	0.0320 (8)	−0.0004 (6)	0.0176 (6)	0.0004 (7)
N2A	0.0198 (6)	0.0182 (8)	0.0200 (7)	0.0004 (5)	0.0124 (6)	−0.0002 (5)
N3A	0.0181 (6)	0.0240 (8)	0.0192 (7)	−0.0002 (5)	0.0093 (6)	0.0018 (6)
C1A	0.0162 (7)	0.0235 (9)	0.0186 (8)	0.0002 (6)	0.0059 (6)	0.0001 (7)
C2A	0.0243 (8)	0.0178 (9)	0.0309 (9)	0.0042 (7)	0.0141 (7)	0.0020 (7)
C3A	0.0233 (8)	0.0199 (9)	0.0260 (9)	0.0005 (7)	0.0128 (7)	0.0033 (7)
C4A	0.0158 (7)	0.0203 (9)	0.0177 (8)	0.0000 (6)	0.0064 (6)	−0.0024 (6)
C5A	0.0163 (7)	0.0168 (9)	0.0207 (8)	0.0011 (6)	0.0036 (6)	−0.0022 (6)
C6A	0.0177 (7)	0.0176 (9)	0.0215 (8)	−0.0022 (6)	0.0064 (6)	0.0005 (7)
C7A	0.0157 (7)	0.0239 (10)	0.0160 (8)	0.0005 (6)	0.0045 (6)	−0.0035 (7)
C8A	0.0192 (7)	0.0134 (8)	0.0191 (8)	−0.0001 (6)	0.0091 (6)	−0.0016 (6)
C9A	0.0195 (7)	0.0208 (9)	0.0278 (9)	0.0012 (6)	0.0139 (7)	−0.0009 (7)
C10A	0.0184 (7)	0.0256 (10)	0.0270 (9)	0.0041 (7)	0.0089 (7)	−0.0003 (7)
C11A	0.0249 (8)	0.0223 (10)	0.0191 (8)	0.0031 (7)	0.0078 (7)	0.0012 (7)
C12A	0.0229 (7)	0.0180 (9)	0.0196 (8)	0.0001 (6)	0.0115 (6)	−0.0002 (6)
C13A	0.0188 (7)	0.0126 (8)	0.0188 (8)	−0.0004 (6)	0.0094 (6)	−0.0024 (6)
C14A	0.0200 (7)	0.0117 (8)	0.0204 (8)	−0.0020 (6)	0.0107 (6)	−0.0034 (6)
C15A	0.0199 (7)	0.0122 (8)	0.0189 (8)	−0.0007 (6)	0.0090 (6)	−0.0019 (6)
C16A	0.0191 (7)	0.0182 (9)	0.0230 (8)	−0.0012 (6)	0.0107 (6)	−0.0021 (7)
C17A	0.0208 (7)	0.0217 (10)	0.0207 (8)	0.0013 (6)	0.0069 (6)	−0.0012 (7)
C18A	0.0284 (8)	0.0227 (10)	0.0168 (8)	0.0008 (7)	0.0086 (7)	−0.0007 (7)
C19A	0.0258 (8)	0.0190 (9)	0.0211 (8)	−0.0009 (6)	0.0133 (7)	−0.0013 (7)
C20A	0.0203 (7)	0.0135 (8)	0.0193 (8)	−0.0016 (6)	0.0101 (6)	−0.0022 (6)
O1B	0.0241 (6)	0.0221 (7)	0.0224 (6)	0.0018 (5)	0.0094 (5)	0.0003 (5)
O2B	0.0246 (6)	0.0209 (7)	0.0302 (7)	−0.0014 (5)	0.0089 (5)	−0.0067 (5)
N1B	0.0218 (7)	0.0222 (9)	0.0235 (8)	−0.0007 (6)	0.0084 (6)	−0.0014 (7)
N2B	0.0231 (7)	0.0204 (8)	0.0160 (7)	0.0007 (6)	0.0072 (6)	0.0002 (6)
N3B	0.0188 (6)	0.0276 (9)	0.0182 (7)	0.0006 (6)	0.0063 (6)	−0.0009 (6)
C1B	0.0154 (7)	0.0233 (9)	0.0221 (8)	−0.0014 (6)	0.0105 (6)	−0.0002 (7)
C2B	0.0245 (8)	0.0179 (9)	0.0296 (9)	0.0019 (7)	0.0098 (7)	0.0005 (7)
C3B	0.0242 (8)	0.0178 (9)	0.0288 (9)	−0.0012 (7)	0.0103 (7)	−0.0046 (7)
C4B	0.0171 (7)	0.0194 (9)	0.0233 (8)	−0.0024 (6)	0.0112 (6)	−0.0019 (7)
C5B	0.0181 (7)	0.0180 (9)	0.0232 (8)	−0.0005 (6)	0.0107 (6)	0.0008 (7)
C6B	0.0208 (7)	0.0171 (9)	0.0281 (9)	−0.0035 (6)	0.0152 (7)	−0.0044 (7)
C7B	0.0175 (7)	0.0218 (9)	0.0238 (8)	−0.0009 (6)	0.0127 (6)	−0.0021 (7)
C8B	0.0241 (8)	0.0141 (9)	0.0229 (8)	−0.0028 (6)	0.0115 (7)	−0.0003 (6)
C9B	0.0275 (8)	0.0246 (10)	0.0199 (8)	−0.0012 (7)	0.0103 (7)	−0.0004 (7)
C10B	0.0274 (8)	0.0259 (10)	0.0285 (9)	0.0002 (7)	0.0154 (7)	−0.0017 (8)
C11B	0.0199 (7)	0.0226 (10)	0.0262 (9)	0.0025 (6)	0.0104 (7)	0.0013 (7)
C12B	0.0208 (7)	0.0214 (10)	0.0227 (8)	−0.0012 (6)	0.0067 (7)	0.0012 (7)
C13B	0.0169 (7)	0.0149 (9)	0.0258 (9)	−0.0012 (6)	0.0087 (6)	0.0009 (7)
C14B	0.0183 (7)	0.0131 (8)	0.0175 (8)	−0.0036 (6)	0.0045 (6)	0.0018 (6)
C15B	0.0168 (7)	0.0133 (8)	0.0173 (7)	−0.0008 (6)	0.0063 (6)	0.0022 (6)
C16B	0.0230 (7)	0.0202 (9)	0.0193 (8)	−0.0020 (6)	0.0099 (6)	0.0007 (7)
C17B	0.0228 (8)	0.0239 (10)	0.0294 (9)	0.0007 (7)	0.0156 (7)	0.0019 (7)
C18B	0.0154 (7)	0.0244 (10)	0.0322 (10)	0.0019 (6)	0.0082 (7)	0.0042 (8)
C19B	0.0197 (7)	0.0226 (10)	0.0189 (8)	−0.0009 (6)	0.0021 (6)	0.0027 (7)
C20B	0.0185 (7)	0.0147 (8)	0.0184 (8)	−0.0024 (6)	0.0065 (6)	0.0007 (6)
O1W	0.0313 (7)	0.0254 (8)	0.0297 (7)	0.0064 (6)	0.0143 (6)	0.0006 (6)
O2W	0.0336 (7)	0.0227 (8)	0.0252 (7)	0.0030 (6)	0.0085 (6)	0.0018 (6)
O3W	0.0266 (6)	0.0280 (8)	0.0281 (7)	−0.0028 (6)	0.0104 (5)	−0.0018 (6)
O4W	0.0265 (6)	0.0227 (7)	0.0247 (7)	0.0024 (5)	0.0110 (5)	−0.0016 (5)

O1A—C7A	1.257 (2)	N1B—H2NB	0.89 (2)
O2A—C7A	1.273 (2)	N2B—C8B	1.363 (2)
N1A—C1A	1.390 (2)	N2B—C20B	1.365 (2)
N1A—H1NA	0.91 (2)	N2B—H3NB	0.98 (2)
N1A—H2NA	0.92 (3)	N3B—C14B	1.317 (2)
N2A—C8A	1.363 (2)	N3B—H4NB	0.99 (2)
N2A—C20A	1.365 (2)	N3B—H5NB	0.898 (9)
N2A—H3NA	0.90 (2)	C1B—C6B	1.396 (2)
N3A—C14A	1.3234 (19)	C1B—C2B	1.404 (2)
N3A—H4NA	0.93 (2)	C2B—C3B	1.383 (2)
N3A—H5NA	0.91 (2)	C2B—H2BA	0.9500
C1A—C2A	1.398 (2)	C3B—C4B	1.395 (2)
C1A—C6A	1.401 (2)	C3B—H3BA	0.9500
C2A—C3A	1.391 (2)	C4B—C5B	1.398 (2)
C2A—H2AA	0.9500	C4B—C7B	1.500 (2)
C3A—C4A	1.390 (2)	C5B—C6B	1.386 (2)
C3A—H3AA	0.9500	C5B—H5BA	0.9500
C4A—C5A	1.398 (2)	C6B—H6BA	0.9500
C4A—C7A	1.504 (2)	C8B—C13B	1.410 (2)
C5A—C6A	1.383 (2)	C8B—C9B	1.413 (2)
C5A—H5AA	0.9500	C9B—C10B	1.366 (2)
C6A—H6AA	0.9500	C9B—H9BA	0.9500
C8A—C9A	1.412 (2)	C10B—C11B	1.415 (2)
C8A—C13A	1.414 (2)	C10B—H10B	0.9500
C9A—C10A	1.370 (2)	C11B—C12B	1.368 (2)
C9A—H9AA	0.9500	C11B—H11B	0.9500
C10A—C11A	1.407 (2)	C12B—C13B	1.424 (2)
C10A—H10A	0.9500	C12B—H12B	0.9500
C11A—C12A	1.367 (2)	C13B—C14B	1.443 (2)
C11A—H11A	0.9500	C14B—C15B	1.438 (2)
C12A—C13A	1.422 (2)	C15B—C20B	1.407 (2)
C12A—H12A	0.9500	C15B—C16B	1.420 (2)
C13A—C14A	1.439 (2)	C16B—C17B	1.362 (2)
C14A—C15A	1.439 (2)	C16B—H16B	0.9500
C15A—C20A	1.415 (2)	C17B—C18B	1.403 (2)
C15A—C16A	1.419 (2)	C17B—H17B	0.9500
C16A—C17A	1.366 (2)	C18B—C19B	1.370 (2)
C16A—H16A	0.9500	C18B—H18B	0.9500
C17A—C18A	1.411 (2)	C19B—C20B	1.416 (2)
C17A—H17A	0.9500	C19B—H19B	0.9500
C18A—C19A	1.368 (2)	O1W—H1W1	0.84 (3)
C18A—H18A	0.9500	O1W—H2W1	0.87 (3)
C19A—C20A	1.411 (2)	O2W—H1W2	0.88 (3)
C19A—H19A	0.9500	O2W—H2W2	0.87 (3)
O1B—C7B	1.273 (2)	O3W—H1W3	0.90 (3)
O2B—C7B	1.256 (2)	O3W—H2W3	0.96 (3)
N1B—C1B	1.381 (2)	O4W—H1W4	0.91 (3)
N1B—H1NB	0.86 (2)	O4W—H2W4	0.87 (3)
C1A—N1A—H1NA	115.8 (13)	H1NB—N1B—H2NB	109 (2)
C1A—N1A—H2NA	117.7 (14)	C8B—N2B—C20B	121.86 (14)
H1NA—N1A—H2NA	115.3 (19)	C8B—N2B—H3NB	111.3 (13)
C8A—N2A—C20A	122.22 (13)	C20B—N2B—H3NB	126.9 (14)
C8A—N2A—H3NA	118.9 (13)	C14B—N3B—H4NB	122.9 (13)
C20A—N2A—H3NA	118.7 (13)	C14B—N3B—H5NB	124.5 (14)
C14A—N3A—H4NA	123.4 (13)	H4NB—N3B—H5NB	112.5 (19)
C14A—N3A—H5NA	121.4 (13)	N1B—C1B—C6B	122.06 (16)
H4NA—N3A—H5NA	115.1 (18)	N1B—C1B—C2B	119.75 (16)
N1A—C1A—C2A	121.01 (16)	C6B—C1B—C2B	118.08 (15)
N1A—C1A—C6A	120.43 (16)	C3B—C2B—C1B	120.71 (17)
C2A—C1A—C6A	118.41 (14)	C3B—C2B—H2BA	119.6
C3A—C2A—C1A	120.60 (16)	C1B—C2B—H2BA	119.6
C3A—C2A—H2AA	119.7	C2B—C3B—C4B	121.29 (17)
C1A—C2A—H2AA	119.7	C2B—C3B—H3BA	119.4
C4A—C3A—C2A	121.16 (16)	C4B—C3B—H3BA	119.4
C4A—C3A—H3AA	119.4	C3B—C4B—C5B	117.89 (15)
C2A—C3A—H3AA	119.4	C3B—C4B—C7B	120.02 (16)
C3A—C4A—C5A	117.87 (14)	C5B—C4B—C7B	122.08 (15)
C3A—C4A—C7A	122.25 (15)	C6B—C5B—C4B	121.15 (16)
C5A—C4A—C7A	119.88 (15)	C6B—C5B—H5BA	119.4
C6A—C5A—C4A	121.61 (16)	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.2	C5B—C6B—C1B	120.81 (16)
C4A—C5A—H5AA	119.2	C5B—C6B—H6BA	119.6
C5A—C6A—C1A	120.28 (16)	C1B—C6B—H6BA	119.6
C5A—C6A—H6AA	119.9	O2B—C7B—O1B	123.11 (15)
C1A—C6A—H6AA	119.9	O2B—C7B—C4B	117.87 (15)
O1A—C7A—O2A	123.20 (14)	O1B—C7B—C4B	119.02 (15)
O1A—C7A—C4A	117.83 (15)	N2B—C8B—C13B	120.76 (14)
O2A—C7A—C4A	118.97 (15)	N2B—C8B—C9B	118.87 (15)
N2A—C8A—C9A	119.55 (14)	C13B—C8B—C9B	120.36 (15)
N2A—C8A—C13A	120.78 (13)	C10B—C9B—C8B	119.75 (16)
C9A—C8A—C13A	119.67 (14)	C10B—C9B—H9BA	120.1
C10A—C9A—C8A	120.19 (14)	C8B—C9B—H9BA	120.1
C10A—C9A—H9AA	119.9	C9B—C10B—C11B	121.14 (16)
C8A—C9A—H9AA	119.9	C9B—C10B—H10B	119.4
C9A—C10A—C11A	120.74 (15)	C11B—C10B—H10B	119.4
C9A—C10A—H10A	119.6	C12B—C11B—C10B	119.38 (15)
C11A—C10A—H10A	119.6	C12B—C11B—H11B	120.3
C12A—C11A—C10A	119.94 (15)	C10B—C11B—H11B	120.3
C12A—C11A—H11A	120.0	C11B—C12B—C13B	121.41 (16)
C10A—C11A—H11A	120.0	C11B—C12B—H12B	119.3
C11A—C12A—C13A	121.01 (14)	C13B—C12B—H12B	119.3
C11A—C12A—H12A	119.5	C8B—C13B—C12B	117.95 (15)
C13A—C12A—H12A	119.5	C8B—C13B—C14B	119.16 (14)
C8A—C13A—C12A	118.41 (14)	C12B—C13B—C14B	122.88 (15)
C8A—C13A—C14A	118.87 (14)	N3B—C14B—C15B	121.28 (15)
C12A—C13A—C14A	122.72 (13)	N3B—C14B—C13B	120.70 (14)
N3A—C14A—C15A	120.96 (14)	C15B—C14B—C13B	118.02 (14)
N3A—C14A—C13A	120.49 (14)	C20B—C15B—C16B	118.28 (14)
C15A—C14A—C13A	118.55 (13)	C20B—C15B—C14B	119.32 (14)
C20A—C15A—C16A	118.08 (14)	C16B—C15B—C14B	122.40 (14)
C20A—C15A—C14A	119.11 (13)	C17B—C16B—C15B	121.18 (15)
C16A—C15A—C14A	122.81 (14)	C17B—C16B—H16B	119.4
C17A—C16A—C15A	121.24 (14)	C15B—C16B—H16B	119.4
C17A—C16A—H16A	119.4	C16B—C17B—C18B	119.99 (15)
C15A—C16A—H16A	119.4	C16B—C17B—H17B	120.0
C16A—C17A—C18A	119.80 (15)	C18B—C17B—H17B	120.0
C16A—C17A—H17A	120.1	C19B—C18B—C17B	120.81 (15)
C18A—C17A—H17A	120.1	C19B—C18B—H18B	119.6
C19A—C18A—C17A	120.89 (15)	C17B—C18B—H18B	119.6
C19A—C18A—H18A	119.6	C18B—C19B—C20B	119.78 (15)
C17A—C18A—H18A	119.6	C18B—C19B—H19B	120.1
C18A—C19A—C20A	119.83 (15)	C20B—C19B—H19B	120.1
C18A—C19A—H19A	120.1	N2B—C20B—C15B	120.86 (14)
C20A—C19A—H19A	120.1	N2B—C20B—C19B	119.18 (14)
N2A—C20A—C19A	119.40 (13)	C15B—C20B—C19B	119.96 (14)
N2A—C20A—C15A	120.45 (14)	H1W1—O1W—H2W1	107 (2)
C19A—C20A—C15A	120.15 (14)	H1W2—O2W—H2W2	108 (2)
C1B—N1B—H1NB	120.6 (15)	H1W3—O3W—H2W3	114 (2)
C1B—N1B—H2NB	119.1 (14)	H1W4—O4W—H2W4	110 (2)
N1A—C1A—C2A—C3A	−173.95 (16)	N1B—C1B—C2B—C3B	174.26 (15)
C6A—C1A—C2A—C3A	1.6 (2)	C6B—C1B—C2B—C3B	−2.1 (2)
C1A—C2A—C3A—C4A	0.7 (3)	C1B—C2B—C3B—C4B	0.0 (3)
C2A—C3A—C4A—C5A	−1.9 (2)	C2B—C3B—C4B—C5B	1.4 (2)
C2A—C3A—C4A—C7A	178.03 (15)	C2B—C3B—C4B—C7B	−179.87 (15)
C3A—C4A—C5A—C6A	0.7 (2)	C3B—C4B—C5B—C6B	−0.7 (2)
C7A—C4A—C5A—C6A	−179.19 (14)	C7B—C4B—C5B—C6B	−179.40 (14)
C4A—C5A—C6A—C1A	1.6 (2)	C4B—C5B—C6B—C1B	−1.4 (2)
N1A—C1A—C6A—C5A	172.84 (15)	N1B—C1B—C6B—C5B	−173.47 (14)
C2A—C1A—C6A—C5A	−2.8 (2)	C2B—C1B—C6B—C5B	2.8 (2)
C3A—C4A—C7A—O1A	−171.22 (15)	C3B—C4B—C7B—O2B	−4.6 (2)
C5A—C4A—C7A—O1A	8.7 (2)	C5B—C4B—C7B—O2B	174.05 (14)
C3A—C4A—C7A—O2A	9.0 (2)	C3B—C4B—C7B—O1B	175.43 (14)
C5A—C4A—C7A—O2A	−171.12 (14)	C5B—C4B—C7B—O1B	−5.9 (2)
C20A—N2A—C8A—C9A	178.09 (16)	C20B—N2B—C8B—C13B	−0.8 (2)
C20A—N2A—C8A—C13A	−1.6 (2)	C20B—N2B—C8B—C9B	178.96 (16)
N2A—C8A—C9A—C10A	177.90 (16)	N2B—C8B—C9B—C10B	−179.17 (17)
C13A—C8A—C9A—C10A	−2.5 (3)	C13B—C8B—C9B—C10B	0.6 (3)
C8A—C9A—C10A—C11A	1.1 (3)	C8B—C9B—C10B—C11B	−0.5 (3)
C9A—C10A—C11A—C12A	0.9 (3)	C9B—C10B—C11B—C12B	0.0 (3)
C10A—C11A—C12A—C13A	−1.4 (3)	C10B—C11B—C12B—C13B	0.5 (3)
N2A—C8A—C13A—C12A	−178.44 (15)	N2B—C8B—C13B—C12B	179.58 (15)
C9A—C8A—C13A—C12A	1.9 (2)	C9B—C8B—C13B—C12B	−0.2 (2)
N2A—C8A—C13A—C14A	1.7 (2)	N2B—C8B—C13B—C14B	−0.2 (2)
C9A—C8A—C13A—C14A	−177.91 (15)	C9B—C8B—C13B—C14B	−179.97 (16)
C11A—C12A—C13A—C8A	0.0 (2)	C11B—C12B—C13B—C8B	−0.3 (3)
C11A—C12A—C13A—C14A	179.83 (16)	C11B—C12B—C13B—C14B	179.42 (17)
C8A—C13A—C14A—N3A	178.94 (16)	C8B—C13B—C14B—N3B	−178.63 (16)
C12A—C13A—C14A—N3A	−0.9 (2)	C12B—C13B—C14B—N3B	1.6 (3)
C8A—C13A—C14A—C15A	−1.2 (2)	C8B—C13B—C14B—C15B	1.0 (2)
C12A—C13A—C14A—C15A	178.99 (15)	C12B—C13B—C14B—C15B	−178.80 (15)
N3A—C14A—C15A—C20A	−179.66 (16)	N3B—C14B—C15B—C20B	178.81 (16)
C13A—C14A—C15A—C20A	0.5 (2)	C13B—C14B—C15B—C20B	−0.8 (2)
N3A—C14A—C15A—C16A	0.2 (2)	N3B—C14B—C15B—C16B	−1.4 (2)
C13A—C14A—C15A—C16A	−179.69 (15)	C13B—C14B—C15B—C16B	179.00 (15)
C20A—C15A—C16A—C17A	−0.2 (2)	C20B—C15B—C16B—C17B	0.0 (2)
C14A—C15A—C16A—C17A	179.94 (16)	C14B—C15B—C16B—C17B	−179.77 (16)
C15A—C16A—C17A—C18A	0.4 (3)	C15B—C16B—C17B—C18B	−0.1 (3)
C16A—C17A—C18A—C19A	−0.6 (3)	C16B—C17B—C18B—C19B	0.6 (3)
C17A—C18A—C19A—C20A	0.4 (3)	C17B—C18B—C19B—C20B	−0.9 (3)
C8A—N2A—C20A—C19A	−179.39 (15)	C8B—N2B—C20B—C15B	1.0 (2)
C8A—N2A—C20A—C15A	0.8 (2)	C8B—N2B—C20B—C19B	−178.62 (16)
C18A—C19A—C20A—N2A	179.99 (16)	C16B—C15B—C20B—N2B	−179.97 (15)
C18A—C19A—C20A—C15A	−0.2 (2)	C14B—C15B—C20B—N2B	−0.2 (2)
C16A—C15A—C20A—N2A	179.90 (15)	C16B—C15B—C20B—C19B	−0.3 (2)
C14A—C15A—C20A—N2A	−0.3 (2)	C14B—C15B—C20B—C19B	179.44 (15)
C16A—C15A—C20A—C19A	0.1 (2)	C18B—C19B—C20B—N2B	−179.56 (16)
C14A—C15A—C20A—C19A	179.93 (15)	C18B—C19B—C20B—C15B	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3W	0.84 (3)	1.92 (3)	2.758 (2)	179 (5)
O1W—H2W1···O1B	0.86 (3)	1.90 (3)	2.767 (2)	177 (2)
O2W—H1W2···O2Ai	0.88 (3)	1.92 (3)	2.8066 (19)	176 (3)
O3W—H2W3···O1Wi	0.96 (3)	1.72 (3)	2.676 (2)	174 (2)
O3W—H1W3···O2Bii	0.90 (3)	1.79 (3)	2.674 (2)	166 (3)
O4W—H2W4···O1A	0.87 (3)	1.84 (3)	2.688 (2)	164 (3)
N1A—H1NA···O2Bi	0.92 (2)	2.09 (2)	2.946 (2)	156.0 (19)
N1A—H2NA···O1Biii	0.92 (3)	2.12 (3)	2.983 (2)	158 (2)
N2A—H3NA···O2Ai	0.90 (2)	1.98 (2)	2.882 (2)	173 (2)
N2B—H3NB···O1Biv	0.98 (2)	1.93 (2)	2.8695 (18)	160 (2)
N3A—H4NA···O4Wv	0.93 (2)	1.93 (2)	2.8227 (19)	161.6 (18)
N3A—H5NA···N1Bvi	0.91 (2)	2.20 (2)	3.031 (2)	151.4 (18)
N3B—H5NB···O3W	0.90 (2)	1.94 (2)	2.819 (2)	165 (2)
N3B—H4NB···N1Ai	1.00 (3)	2.16 (2)	3.067 (2)	151.3 (19)
C12A—H12A···O4Wv	0.95	2.55	3.4756 (19)	164
C16B—H16B···O3W	0.95	2.51	3.438 (2)	164
C11A—H11A···Cg13iv	0.95	2.95	3.6659 (19)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg13 is the centroid of the C1A–C6A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3W	0.84 (3)	1.92 (3)	2.758 (2)	179 (5)
O1W—H2W1⋯O1B	0.86 (3)	1.90 (3)	2.767 (2)	177 (2)
O2W—H1W2⋯O2A i	0.88 (3)	1.92 (3)	2.8066 (19)	176 (3)
O3W—H2W3⋯O1W i	0.96 (3)	1.72 (3)	2.676 (2)	174 (2)
O3W—H1W3⋯O2B ii	0.90 (3)	1.79 (3)	2.674 (2)	166 (3)
O4W—H2W4⋯O1A	0.87 (3)	1.84 (3)	2.688 (2)	164 (3)
N1A—H1NA⋯O2B i	0.92 (2)	2.09 (2)	2.946 (2)	156.0 (19)
N1A—H2NA⋯O1B iii	0.92 (3)	2.12 (3)	2.983 (2)	158 (2)
N2A—H3NA⋯O2A i	0.90 (2)	1.98 (2)	2.882 (2)	173 (2)
N2B—H3NB⋯O1B iv	0.98 (2)	1.93 (2)	2.8695 (18)	160 (2)
N3A—H4NA⋯O4W v	0.93 (2)	1.93 (2)	2.8227 (19)	161.6 (18)
N3A—H5NA⋯N1B vi	0.91 (2)	2.20 (2)	3.031 (2)	151.4 (18)
N3B—H5NB⋯O3W	0.90 (2)	1.94 (2)	2.819 (2)	165 (2)
N3B—H4NB⋯N1A i	1.00 (3)	2.16 (2)	3.067 (2)	151.3 (19)
C12A—H12A⋯O4W v	0.95	2.55	3.4756 (19)	164
C16B—H16B⋯O3W	0.95	2.51	3.438 (2)	164
C11A—H11A⋯Cg13iv	0.95	2.95	3.6659 (19)	133

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