1-Piperonylpiperazinium 4-chloro­benzoate

Kavitha, C.N.; Kaur, M.; Anderson, B.J.; Jasinski, J.P.; Yathirajan, H.S.

doi:10.1107/S1600536814002037

1-Piperonylpiperazinium 4-chlorobenzoate

C. N. Kavitha, M. Kaur, B. J. Anderson, J. P. Jasinski and H. S. Yathirajan

In the title salt {systematic name: 1-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-ium 4-chlorobenzoate}, C₁₂H₁₇N₂O₂⁺·C₇H₄ClO₂⁻, the piperazine ring adopts a slightly disordered chair conformation. The dioxole ring is in a flattened envelope conformation with the methylene C atom forming the flap. The relative orientation of the piperonyl ring system and the piperazine rings is reflected in the N—C—C [pdbond]

C torsion angle of 132.3 (1)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. In the crystal, the components are linked by N—H

O and weak C—H

O hydrogen bonds, forming chains along [010].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814002037/lh5687sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814002037/lh5687Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814002037/lh5687Isup3.cml Supplementary material

CCDC reference: 984052

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.048
wR factor = 0.120
Data-to-parameter ratio = 26.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.092 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Why ?
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          4 Why ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        411

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

1-(3,4-Methylenedioxybenzyl)piperazine or 1-piperonylpiperazine is a psychoactive drug of the piperazine class and is used to synthesise the drug, piribedil, an antiparkinsonian agent (Millan et al., 2001). Piperonylpiperazine derivatives also have α-adrenergic antagonist properties (Gobert et al., 2003) and peripheral vasodilator properties (Gilbert et al., 1968). Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). A review of the current pharmacological and toxicological information for piperazine derivatives is described (Elliott, 2011). The crystal structure of an N-piperonyl analogue of the atypical antipsychotic clozapine (Capuano et al., 2000) is reported. In continuation of our work on salts of piperonylpiperazines, this paper reports the crystal structure of the title compound (I).

The asymmetric unit of (I) consists of a 1-piperonylpiperazinium cation and a p-chlorobenzoate anion (Fig. 1). The piperazine ring in the cation adopts a slightly disordered chair conformation (puckering parameters Q, θ, and φ = 0.5761 (14) Å , 177.7 (2) ° and 177 (4) °; (Cremer & Pople, 1975). The dioxole group is in a slightly distorted envelope configuration (puckering parameters Q and φ = 0.1693 (15) Å and 36.1 (5) ° with atom C5A displaced by 0.2683 (18) Å from the plane through the other four atoms). The piperonyl ring system and the piperazine rings are twisted with respect to each other as reflected in the N1A-C1A-C2A-C8A torsion angle of 132.2 (5)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, N—H···O hydrogen bonds and a weak C10A—H10A···O2Bⁱⁱⁱ intermolecular interactions are observed which influence the crystal packing stability forming 1-D chains along [0 1 0] (Fig. 2).

Related literature top

For the biological activity of related compounds, see: Brockunier et al. (2004); Bogatcheva et al. (2006); Elliott (2011); Gilbert et al. (1968); Gobert et al. (2003); Millan et al. (2001). For a related structure, see: Capuano et al. (2000). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

1-piperonylpiperazine ( 2.2 g, 0.01 mol) and p-chlorobenzoic acid (1.56 g, 0.01 mol) were dissolved in hot N,N-dimethylformamide and stirred for 10 mins at 323 K. The resulting solution was allowed to cool slowly at room temperature. The crystals of the title salt appeared after a few days and were suitable for X-ray studies (m.p.:464-470 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) in OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) with 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of (I) viewed along the c axis. Dashed lines indicate N—H···O and weak C—H···O interactions forming infinite 1-D chains along the b axis. H atoms not involved in hydrogen bonding have been removed for clarity.

1-[(1,3-Benzodioxol-5-yl)methyl]piperazin-1-ium 4-chlorobenzoate top

Crystal data top

C₁₂H₁₇N₂O₂⁺·C₇H₄ClO₂⁻	F(000) = 792
M_r = 376.83	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.9967 (6) Å	Cell parameters from 5056 reflections
b = 8.5990 (3) Å	θ = 3.1–32.8°
c = 12.4150 (5) Å	µ = 0.24 mm⁻¹
β = 90.923 (3)°	T = 173 K
V = 1814.27 (12) Å³	Irregular, light yellow
Z = 4	0.48 × 0.26 × 0.18 mm

Data collection top

Agilent Gemini EOS diffractometer	6302 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4472 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.033
ω scans	θ_max = 32.8°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −21→25
T_min = 0.787, T_max = 1.000	k = −12→12
22917 measured reflections	l = −17→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0455P)² + 0.5274P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
6302 reflections	Δρ_max = 0.30 e Å⁻³
235 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Crystal data top

C₁₂H₁₇N₂O₂⁺·C₇H₄ClO₂⁻	V = 1814.27 (12) Å³
M_r = 376.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.9967 (6) Å	µ = 0.24 mm⁻¹
b = 8.5990 (3) Å	T = 173 K
c = 12.4150 (5) Å	0.48 × 0.26 × 0.18 mm
β = 90.923 (3)°

Data collection top

Agilent Gemini EOS diffractometer	6302 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	4472 reflections with I > 2σ(I)
T_min = 0.787, T_max = 1.000	R_int = 0.033
22917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
6302 reflections	Δρ_min = −0.32 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.46343 (6)	0.65641 (14)	0.06488 (9)	0.0439 (3)
O2A	0.55838 (7)	0.84302 (13)	0.03707 (9)	0.0452 (3)
N1A	0.79257 (6)	0.70236 (13)	0.30762 (9)	0.0280 (2)
N2A	0.95243 (6)	0.60800 (13)	0.27472 (10)	0.0298 (2)
H2AA	0.9590	0.5293	0.3218	0.036*
H2AB	0.9978	0.6209	0.2395	0.036*
C1A	0.71612 (8)	0.69075 (19)	0.35969 (12)	0.0360 (3)
H1AA	0.7072	0.7843	0.4014	0.043*
H1AB	0.7170	0.6033	0.4090	0.043*
C2A	0.64927 (8)	0.66996 (16)	0.27979 (11)	0.0301 (3)
C3A	0.64318 (8)	0.77080 (16)	0.19132 (11)	0.0321 (3)
H3A	0.6810	0.8466	0.1789	0.039*
C4A	0.57955 (8)	0.75298 (16)	0.12438 (11)	0.0304 (3)
C5A	0.49379 (11)	0.7623 (2)	−0.01222 (14)	0.0474 (4)
H5AA	0.4533	0.8355	−0.0346	0.057*
H5AB	0.5113	0.7063	−0.0753	0.057*
C6A	0.52267 (8)	0.64112 (17)	0.14120 (11)	0.0312 (3)
C7A	0.52767 (9)	0.54095 (18)	0.22546 (12)	0.0373 (3)
H7A	0.4895	0.4654	0.2367	0.045*
C8A	0.59275 (9)	0.55669 (18)	0.29434 (12)	0.0352 (3)
H8A	0.5983	0.4885	0.3521	0.042*
C9A	0.85456 (8)	0.73757 (16)	0.38737 (11)	0.0305 (3)
H9AA	0.8570	0.6553	0.4408	0.037*
H9AB	0.8422	0.8340	0.4239	0.037*
C10A	0.93326 (8)	0.75244 (15)	0.33388 (12)	0.0313 (3)
H10A	0.9320	0.8395	0.2842	0.038*
H10B	0.9738	0.7727	0.3880	0.038*
C11A	0.88861 (8)	0.56853 (18)	0.19658 (12)	0.0349 (3)
H11A	0.9003	0.4701	0.1621	0.042*
H11B	0.8854	0.6479	0.1412	0.042*
C12A	0.81076 (8)	0.55708 (16)	0.25287 (12)	0.0316 (3)
H12A	0.7695	0.5336	0.2005	0.038*
H12B	0.8129	0.4730	0.3049	0.038*
Cl1B	0.33436 (2)	0.68123 (5)	0.27279 (3)	0.04524 (12)
O1B	0.02434 (6)	0.65334 (11)	0.59960 (8)	0.0335 (2)
O2B	0.07906 (6)	0.87721 (13)	0.65085 (9)	0.0411 (3)
C1B	0.14214 (7)	0.73384 (14)	0.51518 (10)	0.0255 (2)
C2B	0.21013 (8)	0.82354 (16)	0.52310 (12)	0.0308 (3)
H2B	0.2152	0.8966	0.5780	0.037*
C3B	0.27034 (8)	0.80532 (16)	0.45013 (12)	0.0339 (3)
H3B	0.3161	0.8642	0.4562	0.041*
C4B	0.26105 (8)	0.69800 (16)	0.36822 (11)	0.0310 (3)
C5B	0.19465 (8)	0.60586 (16)	0.35906 (11)	0.0311 (3)
H5B	0.1897	0.5333	0.3038	0.037*
C6B	0.13543 (8)	0.62363 (15)	0.43395 (11)	0.0284 (3)
H6B	0.0909	0.5610	0.4296	0.034*
C7B	0.07682 (8)	0.75601 (15)	0.59450 (11)	0.0275 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0290 (5)	0.0598 (7)	0.0426 (6)	−0.0056 (5)	−0.0065 (4)	0.0000 (5)
O2A	0.0446 (6)	0.0445 (6)	0.0461 (6)	−0.0058 (5)	−0.0140 (5)	0.0112 (5)
N1A	0.0247 (5)	0.0295 (5)	0.0297 (6)	0.0009 (4)	−0.0029 (4)	−0.0040 (4)
N2A	0.0248 (5)	0.0248 (5)	0.0398 (6)	0.0004 (4)	−0.0013 (4)	0.0035 (5)
C1A	0.0289 (7)	0.0482 (9)	0.0310 (7)	0.0017 (6)	0.0001 (5)	−0.0022 (6)
C2A	0.0243 (6)	0.0350 (7)	0.0311 (6)	0.0031 (5)	0.0028 (5)	−0.0031 (5)
C3A	0.0278 (6)	0.0295 (7)	0.0391 (7)	−0.0028 (5)	0.0005 (5)	−0.0004 (5)
C4A	0.0292 (6)	0.0292 (6)	0.0328 (7)	0.0029 (5)	0.0012 (5)	−0.0007 (5)
C5A	0.0497 (10)	0.0517 (10)	0.0403 (8)	−0.0057 (8)	−0.0118 (7)	−0.0001 (7)
C6A	0.0226 (6)	0.0374 (7)	0.0337 (7)	0.0002 (5)	0.0022 (5)	−0.0067 (6)
C7A	0.0312 (7)	0.0422 (8)	0.0387 (8)	−0.0097 (6)	0.0072 (6)	−0.0005 (6)
C8A	0.0341 (7)	0.0399 (8)	0.0317 (7)	−0.0015 (6)	0.0058 (5)	0.0035 (6)
C9A	0.0309 (7)	0.0293 (6)	0.0310 (6)	0.0010 (5)	−0.0055 (5)	−0.0025 (5)
C10A	0.0287 (6)	0.0239 (6)	0.0411 (7)	−0.0019 (5)	−0.0072 (5)	−0.0013 (5)
C11A	0.0304 (7)	0.0355 (7)	0.0385 (7)	0.0033 (5)	−0.0030 (6)	−0.0084 (6)
C12A	0.0276 (6)	0.0276 (6)	0.0393 (7)	−0.0002 (5)	−0.0049 (5)	−0.0056 (5)
Cl1B	0.0359 (2)	0.0490 (2)	0.0512 (2)	−0.00034 (16)	0.01216 (16)	0.00508 (18)
O1B	0.0296 (5)	0.0288 (5)	0.0421 (6)	−0.0036 (4)	0.0024 (4)	0.0014 (4)
O2B	0.0365 (6)	0.0362 (5)	0.0509 (6)	−0.0063 (4)	0.0073 (5)	−0.0127 (5)
C1B	0.0249 (6)	0.0224 (6)	0.0289 (6)	0.0012 (4)	−0.0045 (5)	0.0052 (5)
C2B	0.0282 (6)	0.0271 (6)	0.0369 (7)	−0.0019 (5)	−0.0059 (5)	−0.0003 (5)
C3B	0.0250 (6)	0.0303 (7)	0.0463 (8)	−0.0035 (5)	−0.0036 (5)	0.0042 (6)
C4B	0.0248 (6)	0.0321 (7)	0.0362 (7)	0.0033 (5)	0.0005 (5)	0.0084 (5)
C5B	0.0299 (6)	0.0313 (7)	0.0322 (7)	0.0020 (5)	−0.0043 (5)	−0.0003 (5)
C6B	0.0240 (6)	0.0281 (6)	0.0330 (7)	−0.0018 (5)	−0.0052 (5)	0.0030 (5)
C7B	0.0261 (6)	0.0253 (6)	0.0309 (6)	0.0024 (5)	−0.0046 (5)	0.0031 (5)

Geometric parameters (Å, º) top

O1A—C5A	1.424 (2)	C9A—H9AA	0.9700
O1A—C6A	1.3777 (17)	C9A—H9AB	0.9700
O2A—C4A	1.3753 (17)	C9A—C10A	1.508 (2)
O2A—C5A	1.4281 (19)	C10A—H10A	0.9700
N1A—C1A	1.4640 (17)	C10A—H10B	0.9700
N1A—C9A	1.4658 (16)	C11A—H11A	0.9700
N1A—C12A	1.4578 (17)	C11A—H11B	0.9700
N2A—H2AA	0.9000	C11A—C12A	1.510 (2)
N2A—H2AB	0.9000	C12A—H12A	0.9700
N2A—C10A	1.4818 (17)	C12A—H12B	0.9700
N2A—C11A	1.4829 (18)	Cl1B—C4B	1.7391 (14)
C1A—H1AA	0.9700	O1B—C7B	1.2573 (16)
C1A—H1AB	0.9700	O2B—C7B	1.2554 (16)
C1A—C2A	1.5069 (19)	C1B—C2B	1.3916 (18)
C2A—C3A	1.4019 (19)	C1B—C6B	1.3873 (18)
C2A—C8A	1.382 (2)	C1B—C7B	1.5079 (18)
C3A—H3A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.3619 (19)	C2B—C3B	1.386 (2)
C4A—C6A	1.3820 (19)	C3B—H3B	0.9300
C5A—H5AA	0.9700	C3B—C4B	1.380 (2)
C5A—H5AB	0.9700	C4B—C5B	1.382 (2)
C6A—C7A	1.357 (2)	C5B—H5B	0.9300
C7A—H7A	0.9300	C5B—C6B	1.3896 (19)
C7A—C8A	1.394 (2)	C6B—H6B	0.9300
C8A—H8A	0.9300

C6A—O1A—C5A	104.75 (11)	N1A—C9A—C10A	110.67 (11)
C4A—O2A—C5A	104.70 (12)	H9AA—C9A—H9AB	108.1
C1A—N1A—C9A	110.44 (11)	C10A—C9A—H9AA	109.5
C12A—N1A—C1A	110.11 (11)	C10A—C9A—H9AB	109.5
C12A—N1A—C9A	109.66 (10)	N2A—C10A—C9A	110.53 (11)
H2AA—N2A—H2AB	108.1	N2A—C10A—H10A	109.5
C10A—N2A—H2AA	109.5	N2A—C10A—H10B	109.5
C10A—N2A—H2AB	109.5	C9A—C10A—H10A	109.5
C10A—N2A—C11A	110.60 (10)	C9A—C10A—H10B	109.5
C11A—N2A—H2AA	109.5	H10A—C10A—H10B	108.1
C11A—N2A—H2AB	109.5	N2A—C11A—H11A	109.6
N1A—C1A—H1AA	109.1	N2A—C11A—H11B	109.6
N1A—C1A—H1AB	109.1	N2A—C11A—C12A	110.45 (12)
N1A—C1A—C2A	112.49 (11)	H11A—C11A—H11B	108.1
H1AA—C1A—H1AB	107.8	C12A—C11A—H11A	109.6
C2A—C1A—H1AA	109.1	C12A—C11A—H11B	109.6
C2A—C1A—H1AB	109.1	N1A—C12A—C11A	110.74 (11)
C3A—C2A—C1A	119.20 (13)	N1A—C12A—H12A	109.5
C8A—C2A—C1A	121.06 (13)	N1A—C12A—H12B	109.5
C8A—C2A—C3A	119.71 (13)	C11A—C12A—H12A	109.5
C2A—C3A—H3A	121.4	C11A—C12A—H12B	109.5
C4A—C3A—C2A	117.16 (13)	H12A—C12A—H12B	108.1
C4A—C3A—H3A	121.4	C2B—C1B—C7B	120.21 (12)
O2A—C4A—C6A	109.64 (12)	C6B—C1B—C2B	119.24 (12)
C3A—C4A—O2A	127.79 (13)	C6B—C1B—C7B	120.56 (11)
C3A—C4A—C6A	122.46 (13)	C1B—C2B—H2B	119.6
O1A—C5A—O2A	107.89 (12)	C3B—C2B—C1B	120.80 (13)
O1A—C5A—H5AA	110.1	C3B—C2B—H2B	119.6
O1A—C5A—H5AB	110.1	C2B—C3B—H3B	120.7
O2A—C5A—H5AA	110.1	C4B—C3B—C2B	118.69 (13)
O2A—C5A—H5AB	110.1	C4B—C3B—H3B	120.7
H5AA—C5A—H5AB	108.4	C3B—C4B—Cl1B	118.85 (11)
O1A—C6A—C4A	109.57 (13)	C3B—C4B—C5B	121.83 (13)
C7A—C6A—O1A	128.82 (13)	C5B—C4B—Cl1B	119.31 (11)
C7A—C6A—C4A	121.54 (13)	C4B—C5B—H5B	120.6
C6A—C7A—H7A	121.6	C4B—C5B—C6B	118.77 (13)
C6A—C7A—C8A	116.78 (13)	C6B—C5B—H5B	120.6
C8A—C7A—H7A	121.6	C1B—C6B—C5B	120.64 (12)
C2A—C8A—C7A	122.33 (14)	C1B—C6B—H6B	119.7
C2A—C8A—H8A	118.8	C5B—C6B—H6B	119.7
C7A—C8A—H8A	118.8	O1B—C7B—C1B	118.33 (12)
N1A—C9A—H9AA	109.5	O2B—C7B—O1B	124.75 (13)
N1A—C9A—H9AB	109.5	O2B—C7B—C1B	116.92 (12)

O1A—C6A—C7A—C8A	−176.43 (14)	C6A—C7A—C8A—C2A	1.1 (2)
O2A—C4A—C6A—O1A	0.07 (16)	C8A—C2A—C3A—C4A	1.3 (2)
O2A—C4A—C6A—C7A	−177.15 (13)	C9A—N1A—C1A—C2A	174.49 (12)
N1A—C1A—C2A—C3A	−49.87 (18)	C9A—N1A—C12A—C11A	−59.59 (14)
N1A—C1A—C2A—C8A	132.26 (14)	C10A—N2A—C11A—C12A	−55.32 (15)
N1A—C9A—C10A—N2A	−57.53 (14)	C11A—N2A—C10A—C9A	55.29 (14)
N2A—C11A—C12A—N1A	57.83 (15)	C12A—N1A—C1A—C2A	−64.26 (15)
C1A—N1A—C9A—C10A	−179.02 (11)	C12A—N1A—C9A—C10A	59.46 (14)
C1A—N1A—C12A—C11A	178.69 (11)	Cl1B—C4B—C5B—C6B	−178.09 (10)
C1A—C2A—C3A—C4A	−176.59 (13)	C1B—C2B—C3B—C4B	1.0 (2)
C1A—C2A—C8A—C7A	175.95 (13)	C2B—C1B—C6B—C5B	−2.03 (19)
C2A—C3A—C4A—O2A	175.68 (13)	C2B—C1B—C7B—O1B	−165.32 (12)
C2A—C3A—C4A—C6A	0.0 (2)	C2B—C1B—C7B—O2B	14.80 (18)
C3A—C2A—C8A—C7A	−1.9 (2)	C2B—C3B—C4B—Cl1B	177.00 (10)
C3A—C4A—C6A—O1A	176.46 (13)	C2B—C3B—C4B—C5B	−1.9 (2)
C3A—C4A—C6A—C7A	−0.8 (2)	C3B—C4B—C5B—C6B	0.8 (2)
C4A—O2A—C5A—O1A	18.16 (18)	C4B—C5B—C6B—C1B	1.22 (19)
C4A—C6A—C7A—C8A	0.2 (2)	C6B—C1B—C2B—C3B	0.89 (19)
C5A—O1A—C6A—C4A	11.18 (16)	C6B—C1B—C7B—O1B	14.36 (18)
C5A—O1A—C6A—C7A	−171.86 (16)	C6B—C1B—C7B—O2B	−165.52 (12)
C5A—O2A—C4A—C3A	172.60 (15)	C7B—C1B—C2B—C3B	−179.42 (12)
C5A—O2A—C4A—C6A	−11.25 (16)	C7B—C1B—C6B—C5B	178.29 (11)
C6A—O1A—C5A—O2A	−18.11 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···O1Bⁱ	0.90	1.87	2.7606 (15)	171
N2A—H2AB···O2Bⁱⁱ	0.90	1.78	2.6684 (16)	169
C10A—H10A···O2Bⁱⁱⁱ	0.97	2.57	3.1974 (17)	122

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