Crystal structure of 2-acetyl-5-(3,4-di-meth-oxy-phen-yl)-6-eth-oxy-carbonyl-3,7-dimethyl-5H-thia-zolo[3,2-a]pyrimidin-8-ium chloride.

The title mol-ecular salt, C21H25N2O5S(+)·Cl(-), crystallizes with two ion pairs in the asymmetric unit. The cations have similar conformations (r.m.s. overlay fit = 0.40 Å), with one of them showing disorder of the terminal methyl group of the ester in a 0.72 (2):0.28 (2) ratio. In the first cation, the 3,4-dimeth-oxy-substituted phenyl ring subtends a dihedral angle of 88.38 (7)° with the pyrimidine ring and 6.79 (8)° with the thia-zole ring. The equivalent data for the second cation are 89.97 (3) and 6.42 (7)°, respectively. The pyrimidine ring adopts a sofa conformation in each cation. In the crystal, the components are linked by N-H⋯Cl hydrogen bonds, generating isolated ion pairs. The ion pairs are are linked by C-H⋯O inter-actions, generating a three-dimensional network. In addition, a weak C-H⋯π inter-action is observed.

Related literature

For the pharmacological properties of pyrimidine derivatives, see: Ashok et al. (2007 ▸); Alam et al. (2010 ▸); Kulakov et al. (2009 ▸); Zhi et al. (2008 ▸). For conformational effects on biological activity, see: Rovnyak et al. (1995 ▸). For related structures, see: Prasad et al. (2014 ▸); Nagarajaiah et al. (2012 ▸).

Experimental

Crystal data

C21H25N2O5S+·Cl−

M = 452.94

Triclinic,

a = 9.9000 (6) Å

b = 11.8563 (7) Å

c = 19.0377 (11) Å

α = 80.827 (2)°

β = 83.999 (2)°

γ = 86.071 (2)°

V = 2190.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▸) T min = 0.947, T max = 0.953

26782 measured reflections

7693 independent reflections

4545 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.134

S = 0.97

7693 reflections

565 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1998 ▸); cell refinement: SAINT-Plus (Bruker, 1998 ▸); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and CAMERON (Watkin et al., 1996 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016229/hb7484sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016229/hb7484Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016229/hb7484Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016229/hb7484fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015016229/hb7484fig2.tif

Unit-cell packing of the title compound showing C—H⋯O and N—H⋯Cl inter­actions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

Click here for additional data file.

. DOI: 10.1107/S2056989015016229/hb7484fig3.tif

Unit-cell packing depicting the inter­molecular C—H⋯π inter­actions with dotted lines.

CCDC reference: 1421372

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

C21H25N2O5S+·Cl−	Z = 4
Mr = 452.94	F(000) = 952
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9000 (6) Å	Cell parameters from 7693 reflections
b = 11.8563 (7) Å	θ = 2.1–25.0°
c = 19.0377 (11) Å	µ = 0.31 mm−1
α = 80.827 (2)°	T = 100 K
β = 83.999 (2)°	Block, colorless
γ = 86.071 (2)°	0.40 × 0.35 × 0.30 mm
V = 2190.9 (2) Å3

Bruker SMART APEX CCD diffractometer	7693 independent reflections
Radiation source: fine-focus sealed tube	4545 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.947, Tmax = 0.953	k = −14→14
26782 measured reflections	l = −22→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3
7693 reflections	(Δ/σ)max = 0.001
565 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
S1A	0.55372 (9)	0.82102 (7)	0.06988 (5)	0.0231 (2)
S1B	1.58661 (9)	0.56682 (7)	0.41046 (5)	0.0236 (2)
Cl1A	0.26054 (8)	0.98395 (7)	0.07281 (4)	0.0258 (2)
O3B	1.1844 (2)	0.61890 (18)	0.07522 (11)	0.0219 (6)
O3A	0.9580 (2)	0.78589 (18)	0.40798 (11)	0.0233 (6)
N1A	0.5318 (3)	1.0231 (2)	0.11824 (14)	0.0216 (7)
H1A	0.4428	1.0205	0.1199	0.026*
N2A	0.7460 (3)	0.9302 (2)	0.10151 (13)	0.0183 (7)
O4A	1.1459 (2)	0.82817 (19)	0.30585 (12)	0.0274 (6)
O4B	0.9931 (2)	0.58909 (18)	0.17602 (11)	0.0248 (6)
O2A	0.9189 (2)	1.20032 (18)	0.15574 (12)	0.0255 (6)
N2B	1.3831 (3)	0.4659 (2)	0.38338 (13)	0.0183 (6)
C11A	0.7792 (3)	0.8628 (3)	0.33236 (17)	0.0200 (8)
H11A	0.7091	0.8437	0.3696	0.024*
O5A	0.6313 (2)	0.61710 (19)	0.01754 (13)	0.0312 (6)
N1B	1.5897 (3)	0.3652 (2)	0.36194 (14)	0.0243 (7)
H1B	1.6789	0.3658	0.3554	0.029*
C9A	0.8485 (3)	0.9473 (3)	0.21133 (16)	0.0165 (8)
O5B	1.5264 (2)	0.7675 (2)	0.46921 (13)	0.0330 (6)
C14A	0.9846 (3)	0.9182 (3)	0.22318 (17)	0.0192 (8)
H14A	1.0548	0.9376	0.1861	0.023*
O1A	0.7242 (2)	1.2983 (2)	0.18268 (13)	0.0312 (6)
C11B	1.3560 (3)	0.5287 (3)	0.15165 (17)	0.0211 (8)
H11B	1.4278	0.5424	0.1146	0.025*
C13B	1.1196 (3)	0.5473 (3)	0.19403 (17)	0.0188 (8)
C10A	0.7475 (3)	0.9186 (3)	0.26544 (17)	0.0200 (8)
H10A	0.6550	0.9371	0.2571	0.024*
C2B	1.5186 (3)	0.4558 (3)	0.38183 (17)	0.0220 (8)
C17B	1.3250 (3)	0.5635 (3)	0.40926 (16)	0.0197 (8)
C5A	0.8131 (3)	1.0096 (3)	0.13895 (17)	0.0174 (8)
H5A	0.8993	1.0330	0.1097	0.021*
C9B	1.2801 (3)	0.4514 (3)	0.27319 (17)	0.0181 (8)
C19B	1.4225 (3)	0.6284 (3)	0.42452 (17)	0.0204 (8)
C6A	0.7208 (3)	1.1153 (3)	0.14404 (16)	0.0185 (8)
C2A	0.6109 (3)	0.9356 (3)	0.09945 (16)	0.0185 (8)
C21B	1.2888 (3)	0.8079 (3)	0.46114 (18)	0.0283 (9)
H21A	1.2298	0.7711	0.5017	0.042*
H21B	1.2430	0.8144	0.4174	0.042*
H21C	1.3081	0.8844	0.4695	0.042*
C14B	1.1472 (3)	0.4909 (3)	0.26048 (17)	0.0196 (8)
H14B	1.0757	0.4789	0.2978	0.024*
C12A	0.9138 (3)	0.8359 (3)	0.34386 (17)	0.0197 (8)
C13A	1.0166 (3)	0.8614 (3)	0.28869 (17)	0.0184 (8)
C12B	1.2245 (3)	0.5658 (3)	0.13895 (17)	0.0178 (8)
C17A	0.8121 (3)	0.8373 (3)	0.07323 (17)	0.0197 (8)
C20A	0.7354 (4)	0.6582 (3)	0.02851 (17)	0.0237 (8)
C7A	0.5872 (3)	1.1187 (3)	0.13521 (17)	0.0200 (8)
C10B	1.3838 (3)	0.4711 (3)	0.21867 (17)	0.0220 (8)
H10B	1.4745	0.4452	0.2270	0.026*
C5B	1.3078 (3)	0.3898 (3)	0.34687 (17)	0.0204 (8)
H5B	1.2187	0.3740	0.3755	0.025*
C20B	1.4185 (4)	0.7379 (3)	0.45335 (17)	0.0257 (9)
C3A	0.7829 (3)	1.2151 (3)	0.16276 (17)	0.0202 (8)
C6B	1.3908 (4)	0.2779 (3)	0.34601 (17)	0.0218 (8)
C7B	1.5250 (4)	0.2687 (3)	0.35115 (17)	0.0252 (9)
C1A	0.4850 (3)	1.2162 (3)	0.14002 (19)	0.0277 (9)
H1A1	0.4466	1.2143	0.1897	0.042*
H1A2	0.4122	1.2100	0.1100	0.042*
H1A3	0.5291	1.2885	0.1235	0.042*
C19A	0.7212 (3)	0.7669 (3)	0.05676 (17)	0.0210 (8)
C16B	0.8851 (3)	0.5858 (3)	0.23198 (18)	0.0323 (10)
H16A	0.8678	0.5061	0.2517	0.048*
H16B	0.8027	0.6239	0.2129	0.048*
H16C	0.9106	0.6253	0.2697	0.048*
C18A	0.9630 (3)	0.8299 (3)	0.06129 (17)	0.0222 (8)
H18A	0.9998	0.7761	0.1001	0.033*
H18B	0.9977	0.9056	0.0603	0.033*
H18C	0.9908	0.8030	0.0156	0.033*
C15B	1.2870 (3)	0.6565 (3)	0.01999 (18)	0.0291 (9)
H15A	1.3409	0.7123	0.0359	0.044*
H15B	1.2443	0.6921	−0.0229	0.044*
H15C	1.3464	0.5908	0.0089	0.044*
C1B	1.6186 (4)	0.1652 (3)	0.34882 (19)	0.0339 (10)
H1B1	1.5867	0.1038	0.3864	0.051*
H1B2	1.7105	0.1836	0.3565	0.051*
H1B3	1.6202	0.1403	0.3021	0.051*
C18B	1.1749 (3)	0.5825 (3)	0.41897 (18)	0.0243 (9)
H18D	1.1493	0.6179	0.4620	0.036*
H18E	1.1323	0.5091	0.4242	0.036*
H18F	1.1439	0.6332	0.3772	0.036*
C15A	0.8599 (4)	0.7449 (3)	0.46416 (18)	0.0349 (10)
H15D	0.7958	0.8080	0.4749	0.052*
H15E	0.9056	0.7135	0.5068	0.052*
H15F	0.8105	0.6849	0.4496	0.052*
O2B	1.1810 (3)	0.1986 (2)	0.35168 (14)	0.0473 (8)
O1B	1.3641 (3)	0.0864 (2)	0.32700 (16)	0.0561 (9)
C16A	1.2520 (3)	0.8421 (3)	0.24971 (19)	0.0390 (11)
H16D	1.2328	0.8007	0.2116	0.058*
H16E	1.3383	0.8118	0.2680	0.058*
H16F	1.2584	0.9236	0.2307	0.058*
C21A	0.8716 (3)	0.6000 (3)	0.01681 (19)	0.0322 (10)
H21D	0.8623	0.5290	−0.0020	0.048*
H21E	0.9125	0.5824	0.0622	0.048*
H21F	0.9298	0.6504	−0.0176	0.048*
C8A	0.9939 (3)	1.2897 (3)	0.17477 (19)	0.0288 (9)
H8A1	0.9670	1.3005	0.2249	0.035*
H8A2	0.9765	1.3631	0.1432	0.035*
C4A	1.1415 (3)	1.2505 (3)	0.16523 (19)	0.0299 (9)
H4A1	1.1584	1.1814	0.1996	0.045*
H4A2	1.1980	1.3110	0.1734	0.045*
H4A3	1.1642	1.2336	0.1165	0.045*
C3B	1.3152 (4)	0.1763 (3)	0.34012 (19)	0.0322 (10)
C8B	1.0940 (5)	0.1052 (4)	0.3517 (3)	0.0723 (16)
H8B1	1.0246	0.1296	0.3178	0.087*
H8B2	1.1491	0.0396	0.3356	0.087*
C4B	1.0291 (12)	0.0708 (9)	0.4207 (6)	0.053 (3)	0.72 (2)
H4B1	0.9833	0.1376	0.4390	0.080*	0.72 (2)
H4B2	1.0969	0.0359	0.4527	0.080*	0.72 (2)
H4B3	0.9619	0.0149	0.4182	0.080*	0.72 (2)
C4B'	0.975 (2)	0.1130 (18)	0.3817 (19)	0.045 (8)	0.28 (2)
H4B4	0.9286	0.0432	0.3801	0.068*	0.28 (2)
H4B5	0.9250	0.1790	0.3567	0.068*	0.28 (2)
H4B6	0.9785	0.1231	0.4315	0.068*	0.28 (2)
Cl1B	0.87338 (9)	0.39271 (8)	0.39496 (5)	0.0349 (3)

	U11	U22	U33	U12	U13	U23
S1A	0.0175 (5)	0.0254 (5)	0.0285 (5)	−0.0026 (4)	−0.0046 (4)	−0.0088 (4)
S1B	0.0202 (5)	0.0268 (5)	0.0254 (5)	−0.0032 (4)	−0.0064 (4)	−0.0050 (4)
Cl1A	0.0188 (5)	0.0344 (6)	0.0240 (5)	−0.0049 (4)	−0.0049 (4)	−0.0001 (4)
O3B	0.0190 (13)	0.0284 (14)	0.0164 (13)	−0.0025 (11)	0.0002 (11)	0.0012 (11)
O3A	0.0181 (13)	0.0334 (15)	0.0160 (13)	−0.0020 (11)	−0.0025 (11)	0.0039 (11)
N1A	0.0111 (15)	0.0268 (18)	0.0286 (17)	0.0015 (13)	−0.0022 (13)	−0.0096 (14)
N2A	0.0165 (16)	0.0194 (16)	0.0196 (16)	0.0015 (13)	−0.0049 (13)	−0.0035 (13)
O4A	0.0138 (13)	0.0422 (16)	0.0225 (14)	0.0025 (11)	−0.0031 (12)	0.0056 (11)
O4B	0.0176 (14)	0.0328 (15)	0.0211 (13)	0.0024 (11)	−0.0013 (11)	0.0027 (11)
O2A	0.0155 (13)	0.0244 (14)	0.0400 (15)	−0.0045 (10)	−0.0040 (12)	−0.0127 (11)
N2B	0.0184 (17)	0.0186 (17)	0.0177 (16)	−0.0011 (13)	−0.0037 (13)	−0.0009 (13)
C11A	0.020 (2)	0.024 (2)	0.0153 (19)	−0.0058 (16)	0.0018 (16)	−0.0019 (15)
O5A	0.0253 (15)	0.0298 (15)	0.0424 (16)	−0.0015 (12)	−0.0096 (13)	−0.0130 (12)
N1B	0.0200 (17)	0.0266 (18)	0.0275 (17)	−0.0002 (14)	−0.0050 (14)	−0.0064 (14)
C9A	0.0164 (19)	0.0173 (19)	0.0161 (19)	−0.0024 (15)	−0.0009 (16)	−0.0036 (15)
O5B	0.0264 (15)	0.0367 (16)	0.0397 (16)	−0.0065 (12)	−0.0062 (13)	−0.0135 (13)
C14A	0.0156 (19)	0.022 (2)	0.020 (2)	−0.0028 (15)	−0.0014 (16)	−0.0027 (16)
O1A	0.0237 (14)	0.0276 (16)	0.0455 (17)	0.0033 (12)	−0.0050 (13)	−0.0161 (13)
C11B	0.022 (2)	0.023 (2)	0.018 (2)	−0.0075 (16)	0.0024 (16)	−0.0017 (16)
C13B	0.018 (2)	0.018 (2)	0.021 (2)	−0.0011 (15)	−0.0058 (17)	−0.0037 (15)
C10A	0.0190 (19)	0.021 (2)	0.022 (2)	0.0003 (15)	−0.0073 (17)	−0.0043 (16)
C2B	0.020 (2)	0.028 (2)	0.018 (2)	0.0010 (17)	−0.0063 (17)	−0.0013 (16)
C17B	0.025 (2)	0.021 (2)	0.0122 (18)	−0.0003 (16)	−0.0020 (16)	0.0006 (15)
C5A	0.0119 (18)	0.020 (2)	0.0215 (19)	−0.0001 (15)	−0.0024 (16)	−0.0062 (15)
C9B	0.021 (2)	0.019 (2)	0.0145 (19)	−0.0051 (15)	−0.0007 (16)	−0.0014 (15)
C19B	0.019 (2)	0.025 (2)	0.0164 (19)	−0.0001 (16)	−0.0058 (16)	−0.0009 (16)
C6A	0.023 (2)	0.018 (2)	0.0150 (18)	−0.0010 (15)	−0.0026 (16)	−0.0019 (15)
C2A	0.018 (2)	0.025 (2)	0.0139 (19)	−0.0012 (16)	−0.0033 (16)	−0.0035 (15)
C21B	0.031 (2)	0.028 (2)	0.026 (2)	0.0024 (18)	−0.0024 (18)	−0.0051 (17)
C14B	0.018 (2)	0.022 (2)	0.019 (2)	−0.0057 (15)	0.0015 (16)	−0.0055 (16)
C12A	0.024 (2)	0.019 (2)	0.017 (2)	−0.0028 (15)	−0.0078 (17)	−0.0004 (15)
C13A	0.0152 (19)	0.019 (2)	0.020 (2)	0.0012 (15)	−0.0021 (17)	−0.0009 (15)
C12B	0.025 (2)	0.0124 (19)	0.017 (2)	−0.0024 (15)	−0.0081 (17)	−0.0011 (15)
C17A	0.0191 (19)	0.020 (2)	0.0196 (19)	0.0037 (16)	−0.0041 (16)	−0.0025 (16)
C20A	0.026 (2)	0.026 (2)	0.020 (2)	−0.0009 (17)	−0.0056 (17)	−0.0050 (16)
C7A	0.024 (2)	0.018 (2)	0.0186 (19)	−0.0032 (16)	−0.0040 (17)	−0.0020 (15)
C10B	0.018 (2)	0.025 (2)	0.025 (2)	−0.0026 (16)	−0.0078 (17)	−0.0042 (16)
C5B	0.021 (2)	0.021 (2)	0.019 (2)	−0.0047 (16)	−0.0042 (16)	−0.0015 (15)
C20B	0.033 (2)	0.029 (2)	0.014 (2)	−0.0074 (18)	0.0012 (18)	0.0004 (16)
C3A	0.020 (2)	0.022 (2)	0.0182 (19)	0.0014 (16)	−0.0044 (17)	−0.0012 (16)
C6B	0.031 (2)	0.021 (2)	0.0134 (19)	−0.0059 (17)	−0.0053 (17)	−0.0001 (15)
C7B	0.035 (2)	0.026 (2)	0.0145 (19)	0.0016 (18)	−0.0071 (17)	−0.0030 (16)
C1A	0.022 (2)	0.028 (2)	0.035 (2)	0.0023 (17)	−0.0065 (18)	−0.0086 (18)
C19A	0.020 (2)	0.024 (2)	0.020 (2)	−0.0003 (16)	−0.0057 (16)	−0.0027 (16)
C16B	0.021 (2)	0.047 (3)	0.028 (2)	0.0037 (18)	0.0008 (19)	−0.0043 (19)
C18A	0.0162 (19)	0.026 (2)	0.025 (2)	0.0006 (15)	−0.0026 (16)	−0.0060 (16)
C15B	0.031 (2)	0.035 (2)	0.021 (2)	−0.0071 (18)	−0.0069 (18)	0.0009 (17)
C1B	0.041 (2)	0.029 (2)	0.032 (2)	0.0058 (19)	−0.011 (2)	−0.0054 (18)
C18B	0.021 (2)	0.029 (2)	0.025 (2)	0.0015 (16)	−0.0047 (17)	−0.0079 (17)
C15A	0.030 (2)	0.053 (3)	0.018 (2)	−0.010 (2)	−0.0044 (19)	0.0081 (18)
O2B	0.0406 (18)	0.0509 (19)	0.057 (2)	−0.0283 (15)	0.0087 (15)	−0.0242 (15)
O1B	0.062 (2)	0.0254 (18)	0.086 (2)	−0.0040 (15)	−0.0212 (18)	−0.0155 (16)
C16A	0.016 (2)	0.062 (3)	0.031 (2)	0.0072 (19)	−0.0007 (19)	0.010 (2)
C21A	0.031 (2)	0.032 (2)	0.040 (2)	0.0078 (18)	−0.015 (2)	−0.0190 (19)
C8A	0.027 (2)	0.025 (2)	0.038 (2)	−0.0073 (17)	−0.0041 (19)	−0.0133 (18)
C4A	0.022 (2)	0.029 (2)	0.041 (2)	−0.0012 (17)	−0.0060 (19)	−0.0137 (18)
C3B	0.048 (3)	0.028 (3)	0.021 (2)	−0.010 (2)	−0.009 (2)	0.0003 (18)
C8B	0.071 (4)	0.080 (4)	0.078 (4)	−0.057 (3)	0.011 (3)	−0.040 (3)
C4B	0.055 (6)	0.031 (5)	0.072 (7)	−0.016 (4)	0.007 (5)	−0.008 (4)
C4B'	0.034 (12)	0.013 (10)	0.09 (2)	−0.003 (8)	−0.003 (12)	−0.013 (10)
Cl1B	0.0262 (5)	0.0494 (7)	0.0274 (5)	−0.0088 (5)	−0.0059 (4)	0.0044 (5)

S1A—C2A	1.702 (3)	C12A—C13A	1.396 (4)
S1A—C19A	1.744 (3)	C17A—C19A	1.361 (4)
S1B—C2B	1.706 (3)	C17A—C18A	1.485 (4)
S1B—C19B	1.747 (3)	C20A—C19A	1.466 (4)
O3B—C12B	1.360 (3)	C20A—C21A	1.484 (4)
O3B—C15B	1.423 (4)	C7A—C1A	1.491 (4)
O3A—C12A	1.371 (4)	C10B—H10B	0.9500
O3A—C15A	1.416 (4)	C5B—C6B	1.514 (4)
N1A—C2A	1.330 (4)	C5B—H5B	1.0000
N1A—C7A	1.389 (4)	C6B—C7B	1.339 (4)
N1A—H1A	0.8800	C6B—C3B	1.486 (5)
N2A—C2A	1.339 (4)	C7B—C1B	1.490 (4)
N2A—C17A	1.396 (4)	C1A—H1A1	0.9800
N2A—C5A	1.495 (4)	C1A—H1A2	0.9800
O4A—C13A	1.370 (4)	C1A—H1A3	0.9800
O4A—C16A	1.417 (4)	C16B—H16A	0.9800
O4B—C13B	1.372 (4)	C16B—H16B	0.9800
O4B—C16B	1.426 (4)	C16B—H16C	0.9800
O2A—C3A	1.341 (4)	C18A—H18A	0.9800
O2A—C8A	1.447 (3)	C18A—H18B	0.9800
N2B—C2B	1.336 (4)	C18A—H18C	0.9800
N2B—C17B	1.395 (4)	C15B—H15A	0.9800
N2B—C5B	1.501 (4)	C15B—H15B	0.9800
C11A—C12A	1.380 (4)	C15B—H15C	0.9800
C11A—C10A	1.395 (4)	C1B—H1B1	0.9800
C11A—H11A	0.9500	C1B—H1B2	0.9800
O5A—C20A	1.220 (4)	C1B—H1B3	0.9800
N1B—C2B	1.328 (4)	C18B—H18D	0.9800
N1B—C7B	1.401 (4)	C18B—H18E	0.9800
N1B—H1B	0.8800	C18B—H18F	0.9800
C9A—C10A	1.377 (4)	C15A—H15D	0.9800
C9A—C14A	1.400 (4)	C15A—H15E	0.9800
C9A—C5A	1.520 (4)	C15A—H15F	0.9800
O5B—C20B	1.229 (4)	O2B—C3B	1.339 (4)
C14A—C13A	1.376 (4)	O2B—C8B	1.449 (4)
C14A—H14A	0.9500	O1B—C3B	1.192 (4)
O1A—C3A	1.204 (4)	C16A—H16D	0.9800
C11B—C12B	1.379 (4)	C16A—H16E	0.9800
C11B—C10B	1.392 (4)	C16A—H16F	0.9800
C11B—H11B	0.9500	C21A—H21D	0.9800
C13B—C14B	1.378 (4)	C21A—H21E	0.9800
C13B—C12B	1.399 (4)	C21A—H21F	0.9800
C10A—H10A	0.9500	C8A—C4A	1.504 (4)
C17B—C19B	1.356 (4)	C8A—H8A1	0.9900
C17B—C18B	1.485 (4)	C8A—H8A2	0.9900
C5A—C6A	1.510 (4)	C4A—H4A1	0.9800
C5A—H5A	1.0000	C4A—H4A2	0.9800
C9B—C10B	1.385 (4)	C4A—H4A3	0.9800
C9B—C14B	1.399 (4)	C8B—C4B'	1.259 (16)
C9B—C5B	1.517 (4)	C8B—C4B	1.411 (9)
C19B—C20B	1.485 (4)	C8B—H8B1	0.9900
C6A—C7A	1.347 (4)	C8B—H8B2	0.9900
C6A—C3A	1.478 (4)	C4B—H4B1	0.9800
C21B—C20B	1.488 (4)	C4B—H4B2	0.9800
C21B—H21A	0.9800	C4B—H4B3	0.9800
C21B—H21B	0.9800	C4B'—H4B4	0.9800
C21B—H21C	0.9800	C4B'—H4B5	0.9800
C14B—H14B	0.9500	C4B'—H4B6	0.9800
C2A—S1A—C19A	89.49 (15)	O1A—C3A—C6A	126.9 (3)
C2B—S1B—C19B	88.95 (16)	O2A—C3A—C6A	110.1 (3)
C12B—O3B—C15B	118.0 (2)	C7B—C6B—C3B	120.8 (3)
C12A—O3A—C15A	118.4 (3)	C7B—C6B—C5B	122.6 (3)
C2A—N1A—C7A	121.1 (3)	C3B—C6B—C5B	116.5 (3)
C2A—N1A—H1A	119.5	C6B—C7B—N1B	118.5 (3)
C7A—N1A—H1A	119.5	C6B—C7B—C1B	128.0 (3)
C2A—N2A—C17A	113.5 (3)	N1B—C7B—C1B	113.5 (3)
C2A—N2A—C5A	121.4 (3)	C7A—C1A—H1A1	109.5
C17A—N2A—C5A	124.7 (3)	C7A—C1A—H1A2	109.5
C13A—O4A—C16A	117.1 (3)	H1A1—C1A—H1A2	109.5
C13B—O4B—C16B	117.6 (3)	C7A—C1A—H1A3	109.5
C3A—O2A—C8A	116.4 (3)	H1A1—C1A—H1A3	109.5
C2B—N2B—C17B	113.9 (3)	H1A2—C1A—H1A3	109.5
C2B—N2B—C5B	120.8 (3)	C17A—C19A—C20A	133.4 (3)
C17B—N2B—C5B	124.2 (3)	C17A—C19A—S1A	112.3 (3)
C12A—C11A—C10A	119.2 (3)	C20A—C19A—S1A	114.3 (2)
C12A—C11A—H11A	120.4	O4B—C16B—H16A	109.5
C10A—C11A—H11A	120.4	O4B—C16B—H16B	109.5
C2B—N1B—C7B	121.2 (3)	H16A—C16B—H16B	109.5
C2B—N1B—H1B	119.4	O4B—C16B—H16C	109.5
C7B—N1B—H1B	119.4	H16A—C16B—H16C	109.5
C10A—C9A—C14A	119.6 (3)	H16B—C16B—H16C	109.5
C10A—C9A—C5A	120.4 (3)	C17A—C18A—H18A	109.5
C14A—C9A—C5A	119.9 (3)	C17A—C18A—H18B	109.5
C13A—C14A—C9A	119.9 (3)	H18A—C18A—H18B	109.5
C13A—C14A—H14A	120.0	C17A—C18A—H18C	109.5
C9A—C14A—H14A	120.0	H18A—C18A—H18C	109.5
C12B—C11B—C10B	120.1 (3)	H18B—C18A—H18C	109.5
C12B—C11B—H11B	120.0	O3B—C15B—H15A	109.5
C10B—C11B—H11B	120.0	O3B—C15B—H15B	109.5
O4B—C13B—C14B	124.8 (3)	H15A—C15B—H15B	109.5
O4B—C13B—C12B	115.0 (3)	O3B—C15B—H15C	109.5
C14B—C13B—C12B	120.2 (3)	H15A—C15B—H15C	109.5
C9A—C10A—C11A	120.8 (3)	H15B—C15B—H15C	109.5
C9A—C10A—H10A	119.6	C7B—C1B—H1B1	109.5
C11A—C10A—H10A	119.6	C7B—C1B—H1B2	109.5
N1B—C2B—N2B	121.8 (3)	H1B1—C1B—H1B2	109.5
N1B—C2B—S1B	124.8 (3)	C7B—C1B—H1B3	109.5
N2B—C2B—S1B	113.4 (2)	H1B1—C1B—H1B3	109.5
C19B—C17B—N2B	110.8 (3)	H1B2—C1B—H1B3	109.5
C19B—C17B—C18B	128.9 (3)	C17B—C18B—H18D	109.5
N2B—C17B—C18B	120.3 (3)	C17B—C18B—H18E	109.5
N2A—C5A—C6A	109.0 (2)	H18D—C18B—H18E	109.5
N2A—C5A—C9A	109.4 (2)	C17B—C18B—H18F	109.5
C6A—C5A—C9A	113.1 (3)	H18D—C18B—H18F	109.5
N2A—C5A—H5A	108.4	H18E—C18B—H18F	109.5
C6A—C5A—H5A	108.4	O3A—C15A—H15D	109.5
C9A—C5A—H5A	108.4	O3A—C15A—H15E	109.5
C10B—C9B—C14B	119.3 (3)	H15D—C15A—H15E	109.5
C10B—C9B—C5B	121.5 (3)	O3A—C15A—H15F	109.5
C14B—C9B—C5B	119.2 (3)	H15D—C15A—H15F	109.5
C17B—C19B—C20B	133.4 (3)	H15E—C15A—H15F	109.5
C17B—C19B—S1B	112.9 (3)	C3B—O2B—C8B	116.9 (3)
C20B—C19B—S1B	113.6 (2)	O4A—C16A—H16D	109.5
C7A—C6A—C3A	120.8 (3)	O4A—C16A—H16E	109.5
C7A—C6A—C5A	122.6 (3)	H16D—C16A—H16E	109.5
C3A—C6A—C5A	116.5 (3)	O4A—C16A—H16F	109.5
N1A—C2A—N2A	122.3 (3)	H16D—C16A—H16F	109.5
N1A—C2A—S1A	124.5 (2)	H16E—C16A—H16F	109.5
N2A—C2A—S1A	113.2 (2)	C20A—C21A—H21D	109.5
C20B—C21B—H21A	109.5	C20A—C21A—H21E	109.5
C20B—C21B—H21B	109.5	H21D—C21A—H21E	109.5
H21A—C21B—H21B	109.5	C20A—C21A—H21F	109.5
C20B—C21B—H21C	109.5	H21D—C21A—H21F	109.5
H21A—C21B—H21C	109.5	H21E—C21A—H21F	109.5
H21B—C21B—H21C	109.5	O2A—C8A—C4A	105.8 (3)
C13B—C14B—C9B	120.2 (3)	O2A—C8A—H8A1	110.6
C13B—C14B—H14B	119.9	C4A—C8A—H8A1	110.6
C9B—C14B—H14B	119.9	O2A—C8A—H8A2	110.6
O3A—C12A—C11A	124.6 (3)	C4A—C8A—H8A2	110.6
O3A—C12A—C13A	115.0 (3)	H8A1—C8A—H8A2	108.7
C11A—C12A—C13A	120.4 (3)	C8A—C4A—H4A1	109.5
O4A—C13A—C14A	124.7 (3)	C8A—C4A—H4A2	109.5
O4A—C13A—C12A	115.2 (3)	H4A1—C4A—H4A2	109.5
C14A—C13A—C12A	120.0 (3)	C8A—C4A—H4A3	109.5
O3B—C12B—C11B	125.3 (3)	H4A1—C4A—H4A3	109.5
O3B—C12B—C13B	114.9 (3)	H4A2—C4A—H4A3	109.5
C11B—C12B—C13B	119.7 (3)	O1B—C3B—O2B	123.3 (4)
C19A—C17A—N2A	111.1 (3)	O1B—C3B—C6B	126.1 (4)
C19A—C17A—C18A	129.0 (3)	O2B—C3B—C6B	110.5 (3)
N2A—C17A—C18A	119.8 (3)	C4B'—C8B—C4B	43.9 (13)
O5A—C20A—C19A	117.3 (3)	C4B'—C8B—O2B	117.6 (8)
O5A—C20A—C21A	122.3 (3)	C4B—C8B—O2B	110.9 (4)
C19A—C20A—C21A	120.3 (3)	C4B'—C8B—H8B1	66.5
C6A—C7A—N1A	119.4 (3)	C4B—C8B—H8B1	109.5
C6A—C7A—C1A	128.0 (3)	O2B—C8B—H8B1	109.5
N1A—C7A—C1A	112.6 (3)	C4B'—C8B—H8B2	131.7
C9B—C10B—C11B	120.5 (3)	C4B—C8B—H8B2	109.5
C9B—C10B—H10B	119.8	O2B—C8B—H8B2	109.5
C11B—C10B—H10B	119.8	H8B1—C8B—H8B2	108.0
N2B—C5B—C6B	108.0 (3)	C8B—C4B—H4B1	109.5
N2B—C5B—C9B	109.2 (2)	C8B—C4B—H4B2	109.5
C6B—C5B—C9B	113.9 (3)	C8B—C4B—H4B3	109.5
N2B—C5B—H5B	108.5	C8B—C4B'—H4B4	109.5
C6B—C5B—H5B	108.5	C8B—C4B'—H4B5	109.5
C9B—C5B—H5B	108.5	H4B4—C4B'—H4B5	109.5
O5B—C20B—C19B	116.9 (3)	C8B—C4B'—H4B6	109.5
O5B—C20B—C21B	122.5 (3)	H4B4—C4B'—H4B6	109.5
C19B—C20B—C21B	120.6 (3)	H4B5—C4B'—H4B6	109.5
O1A—C3A—O2A	123.0 (3)
C10A—C9A—C14A—C13A	−0.1 (5)	O4B—C13B—C12B—O3B	−2.2 (4)
C5A—C9A—C14A—C13A	−179.8 (3)	C14B—C13B—C12B—O3B	178.0 (3)
C16B—O4B—C13B—C14B	7.6 (4)	O4B—C13B—C12B—C11B	179.1 (3)
C16B—O4B—C13B—C12B	−172.3 (3)	C14B—C13B—C12B—C11B	−0.8 (5)
C14A—C9A—C10A—C11A	1.2 (5)	C2A—N2A—C17A—C19A	−6.3 (4)
C5A—C9A—C10A—C11A	−179.1 (3)	C5A—N2A—C17A—C19A	166.5 (3)
C12A—C11A—C10A—C9A	−0.3 (5)	C2A—N2A—C17A—C18A	170.4 (3)
C7B—N1B—C2B—N2B	−9.0 (5)	C5A—N2A—C17A—C18A	−16.7 (5)
C7B—N1B—C2B—S1B	168.6 (2)	C3A—C6A—C7A—N1A	−179.4 (3)
C17B—N2B—C2B—N1B	176.7 (3)	C5A—C6A—C7A—N1A	−2.3 (5)
C5B—N2B—C2B—N1B	−14.4 (5)	C3A—C6A—C7A—C1A	1.8 (5)
C17B—N2B—C2B—S1B	−1.1 (4)	C5A—C6A—C7A—C1A	178.9 (3)
C5B—N2B—C2B—S1B	167.7 (2)	C2A—N1A—C7A—C6A	−10.8 (5)
C19B—S1B—C2B—N1B	−178.0 (3)	C2A—N1A—C7A—C1A	168.1 (3)
C19B—S1B—C2B—N2B	−0.2 (3)	C14B—C9B—C10B—C11B	−0.6 (5)
C2B—N2B—C17B—C19B	2.3 (4)	C5B—C9B—C10B—C11B	−179.5 (3)
C5B—N2B—C17B—C19B	−166.1 (3)	C12B—C11B—C10B—C9B	−0.5 (5)
C2B—N2B—C17B—C18B	−175.7 (3)	C2B—N2B—C5B—C6B	28.3 (4)
C5B—N2B—C17B—C18B	15.9 (4)	C17B—N2B—C5B—C6B	−164.0 (3)
C2A—N2A—C5A—C6A	−22.7 (4)	C2B—N2B—C5B—C9B	−96.1 (3)
C17A—N2A—C5A—C6A	164.9 (3)	C17B—N2B—C5B—C9B	71.6 (4)
C2A—N2A—C5A—C9A	101.4 (3)	C10B—C9B—C5B—N2B	70.5 (4)
C17A—N2A—C5A—C9A	−70.9 (4)	C14B—C9B—C5B—N2B	−108.3 (3)
C10A—C9A—C5A—N2A	−70.4 (4)	C10B—C9B—C5B—C6B	−50.4 (4)
C14A—C9A—C5A—N2A	109.3 (3)	C14B—C9B—C5B—C6B	130.8 (3)
C10A—C9A—C5A—C6A	51.4 (4)	C17B—C19B—C20B—O5B	171.4 (3)
C14A—C9A—C5A—C6A	−128.9 (3)	S1B—C19B—C20B—O5B	−5.7 (4)
N2B—C17B—C19B—C20B	−179.4 (3)	C17B—C19B—C20B—C21B	−9.5 (6)
C18B—C17B—C19B—C20B	−1.6 (6)	S1B—C19B—C20B—C21B	173.4 (2)
N2B—C17B—C19B—S1B	−2.4 (4)	C8A—O2A—C3A—O1A	1.1 (5)
C18B—C17B—C19B—S1B	175.4 (3)	C8A—O2A—C3A—C6A	−177.9 (3)
C2B—S1B—C19B—C17B	1.5 (3)	C7A—C6A—C3A—O1A	12.5 (5)
C2B—S1B—C19B—C20B	179.2 (3)	C5A—C6A—C3A—O1A	−164.8 (3)
N2A—C5A—C6A—C7A	17.6 (4)	C7A—C6A—C3A—O2A	−168.6 (3)
C9A—C5A—C6A—C7A	−104.3 (3)	C5A—C6A—C3A—O2A	14.1 (4)
N2A—C5A—C6A—C3A	−165.2 (3)	N2B—C5B—C6B—C7B	−23.1 (4)
C9A—C5A—C6A—C3A	72.9 (3)	C9B—C5B—C6B—C7B	98.5 (4)
C7A—N1A—C2A—N2A	5.6 (5)	N2B—C5B—C6B—C3B	156.1 (3)
C7A—N1A—C2A—S1A	−173.7 (2)	C9B—C5B—C6B—C3B	−82.4 (4)
C17A—N2A—C2A—N1A	−174.1 (3)	C3B—C6B—C7B—N1B	−175.3 (3)
C5A—N2A—C2A—N1A	12.8 (5)	C5B—C6B—C7B—N1B	3.8 (5)
C17A—N2A—C2A—S1A	5.3 (4)	C3B—C6B—C7B—C1B	2.9 (5)
C5A—N2A—C2A—S1A	−167.9 (2)	C5B—C6B—C7B—C1B	−178.0 (3)
C19A—S1A—C2A—N1A	177.2 (3)	C2B—N1B—C7B—C6B	14.3 (5)
C19A—S1A—C2A—N2A	−2.2 (3)	C2B—N1B—C7B—C1B	−164.2 (3)
O4B—C13B—C14B—C9B	179.8 (3)	N2A—C17A—C19A—C20A	−177.7 (3)
C12B—C13B—C14B—C9B	−0.3 (5)	C18A—C17A—C19A—C20A	5.9 (6)
C10B—C9B—C14B—C13B	1.0 (5)	N2A—C17A—C19A—S1A	4.6 (4)
C5B—C9B—C14B—C13B	179.9 (3)	C18A—C17A—C19A—S1A	−171.8 (3)
C15A—O3A—C12A—C11A	8.8 (5)	O5A—C20A—C19A—C17A	−178.0 (3)
C15A—O3A—C12A—C13A	−172.5 (3)	C21A—C20A—C19A—C17A	4.3 (6)
C10A—C11A—C12A—O3A	177.0 (3)	O5A—C20A—C19A—S1A	−0.3 (4)
C10A—C11A—C12A—C13A	−1.7 (5)	C21A—C20A—C19A—S1A	−178.1 (3)
C16A—O4A—C13A—C14A	−7.3 (5)	C2A—S1A—C19A—C17A	−1.5 (3)
C16A—O4A—C13A—C12A	174.0 (3)	C2A—S1A—C19A—C20A	−179.7 (3)
C9A—C14A—C13A—O4A	179.5 (3)	C3A—O2A—C8A—C4A	177.7 (3)
C9A—C14A—C13A—C12A	−1.9 (5)	C8B—O2B—C3B—O1B	3.4 (6)
O3A—C12A—C13A—O4A	2.8 (4)	C8B—O2B—C3B—C6B	−176.6 (3)
C11A—C12A—C13A—O4A	−178.5 (3)	C7B—C6B—C3B—O1B	−13.9 (6)
O3A—C12A—C13A—C14A	−176.0 (3)	C5B—C6B—C3B—O1B	166.9 (3)
C11A—C12A—C13A—C14A	2.8 (5)	C7B—C6B—C3B—O2B	166.1 (3)
C15B—O3B—C12B—C11B	−10.9 (4)	C5B—C6B—C3B—O2B	−13.0 (4)
C15B—O3B—C12B—C13B	170.4 (3)	C3B—O2B—C8B—C4B'	160 (2)
C10B—C11B—C12B—O3B	−177.4 (3)	C3B—O2B—C8B—C4B	112.4 (8)
C10B—C11B—C12B—C13B	1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···Cl1A	0.88	2.20	2.993 (1)	151
N1B—H1B···Cl1Bi	0.88	2.20	2.992 (2)	150
C11A—H11A···O5Bii	0.95	2.58	3.523 (1)	173
C15B—H15C···O5Aiii	0.98	2.58	3.456 (6)	148
C21A—H21D···O3Biii	0.98	2.50	3.459 (6)	166
C4A—H4A2···Cg3	0.98	2.63	3.551 (2)	157

Table 1

Hydrogen-bond geometry (, )

Cg3 is the centroid of the C9BC14B ring.

DHA	DH	HA	D A	DHA
N1AH1ACl1A	0.88	2.20	2.993(1)	151
N1BH1BCl1B i	0.88	2.20	2.992(2)	150
C11AH11AO5B ii	0.95	2.58	3.523(1)	173
C15BH15CO5A iii	0.98	2.58	3.456(6)	148
C21AH21DO3B iii	0.98	2.50	3.459(6)	166
C4AH4A2Cg3	0.98	2.63	3.551(2)	157

Symmetry codes: (i) ; (ii) ; (iii) .