Crystal structure of [4-(chloro-meth-yl)phen-yl](4-hy-droxy-piperidin-1-yl)methanone.

The title compound, C13H16ClNO2, crystallized with two independent mol-ecules in the asymmetric unit (A and B). The piperidinol ring in mol-ecule B is disordered over two positions with a site occupancy ratio of 0.667 (5):0.333 (5). In both mol-ecules these rings have a chair conformation, including the minor component in mol-ecule B. Their mean planes are inclined to the benzene ring by 45.57 (13)° in mol-ecule A, and by 50.5 (4)° for the major component of the piperidine ring in mol-ecule B. In the crystal, the individual mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains of A and B mol-ecules along the [100] direction. The chains are inter-linked by C-H⋯O hydrogen bonds, forming ribbons.

Related literature

For the synthesis see: Revathi et al. (2015 ▸). For the biological activity of piperidine derivatives, see: Daly et al. (1986 ▸); Fodor et al. (1985 ▸); Campfield et al. (1995 ▸); Kozikowski et al. (1998 ▸); Brau et al. (2000 ▸); Bolzani et al. (1995 ▸); Gulluoglu et al. (2007 ▸). For related structures see: Revathi et al. (2015 ▸); Prathebha et al. (2015 ▸).

Experimental

Crystal data

C13H16ClNO2

M = 253.72

Triclinic,

a = 8.4131 (3) Å

b = 9.6211 (4) Å

c = 15.6780 (6) Å

α = 80.917 (3)°

β = 89.240 (2)°

γ = 88.395 (2)°

V = 1252.57 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.902, T max = 0.943

28447 measured reflections

4415 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.05

4415 reflections

371 parameters

111 restraints

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Bruno et al., 2002 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015016096/bg2567sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016096/bg2567Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016096/bg2567Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016096/bg2567fig1.tif

The mol­ecular structure of the title compound (left: mol­ecula A; right: mol­ecule B), with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015016096/bg2567fig2.tif

The packing of the mol­ecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

CCDC reference: 1421009

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

C13H16ClNO2	Z = 4
Mr = 253.72	F(000) = 536
Triclinic, P1	Dx = 1.345 Mg m−3
a = 8.4131 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6211 (4) Å	Cell parameters from 9919 reflections
c = 15.6780 (6) Å	θ = 2.3–28.1°
α = 80.917 (3)°	µ = 0.29 mm−1
β = 89.240 (2)°	T = 293 K
γ = 88.395 (2)°	Block, colourless
V = 1252.57 (8) Å3	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	4415 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.902, Tmax = 0.943	k = −11→11
28447 measured reflections	l = −18→18

Refinement on F2	111 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0477P)2 + 1.0906P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4415 reflections	Δρmax = 0.45 e Å−3
371 parameters	Δρmin = −0.61 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)
C1	1.1123 (3)	0.3281 (3)	−0.11147 (15)	0.0386 (5)
C2	1.0000 (3)	0.2251 (3)	−0.10479 (15)	0.0413 (6)
H2	0.9657	0.1937	−0.1544	0.050*
C3	0.9381 (3)	0.1683 (3)	−0.02565 (16)	0.0408 (6)
H3	0.8600	0.1011	−0.0223	0.049*
C4	0.9916 (2)	0.2108 (2)	0.04902 (15)	0.0347 (5)
C5	1.1051 (3)	0.3129 (3)	0.04244 (16)	0.0409 (6)
H5	1.1425	0.3421	0.0921	0.049*
C6	1.1633 (3)	0.3716 (3)	−0.03693 (16)	0.0449 (6)
H6	1.2381	0.4416	−0.0405	0.054*
C7	0.9414 (3)	0.1401 (2)	0.13670 (15)	0.0369 (5)
C8	0.6599 (3)	0.2173 (3)	0.10907 (17)	0.0449 (6)
H8A	0.7011	0.2648	0.0544	0.054*
H8B	0.6232	0.2885	0.1427	0.054*
C9	0.5227 (3)	0.1276 (3)	0.09289 (17)	0.0480 (6)
H9A	0.5571	0.0624	0.0546	0.058*
H9B	0.4377	0.1872	0.0647	0.058*
C10	0.4611 (3)	0.0460 (3)	0.17647 (17)	0.0448 (6)
H10	0.4214	0.1130	0.2133	0.054*
C11	0.5957 (3)	−0.0414 (3)	0.22218 (19)	0.0545 (7)
H11A	0.6322	−0.1113	0.1876	0.065*
H11B	0.5578	−0.0904	0.2772	0.065*
C12	0.7328 (3)	0.0503 (3)	0.23722 (16)	0.0538 (7)
H12A	0.6993	0.1144	0.2763	0.065*
H12B	0.8201	−0.0084	0.2637	0.065*
C13	1.1795 (3)	0.3886 (3)	−0.19750 (17)	0.0512 (7)
H13A	1.1600	0.3256	−0.2385	0.061*
H13B	1.2937	0.3963	−0.1928	0.061*
C14	0.3857 (3)	0.4916 (3)	0.28225 (15)	0.0401 (6)
C15	0.3397 (3)	0.3530 (3)	0.30142 (16)	0.0449 (6)
H15	0.2663	0.3191	0.2665	0.054*
C16	0.4011 (3)	0.2651 (3)	0.37143 (16)	0.0423 (6)
H16	0.3673	0.1728	0.3841	0.051*
C17	0.5127 (3)	0.3125 (2)	0.42329 (14)	0.0348 (5)
C18	0.5592 (3)	0.4505 (3)	0.40463 (15)	0.0412 (6)
H18	0.6343	0.4836	0.4390	0.049*
C19	0.4949 (3)	0.5397 (3)	0.33533 (16)	0.0418 (6)
H19	0.5252	0.6330	0.3242	0.050*
C20	0.5672 (3)	0.2185 (3)	0.50338 (15)	0.0376 (5)
C26	0.3178 (3)	0.5885 (3)	0.20677 (17)	0.0529 (7)
H26A	0.3322	0.6854	0.2146	0.063*
H26B	0.2045	0.5738	0.2036	0.063*
O1	1.04414 (19)	0.0877 (2)	0.18842 (11)	0.0515 (5)
N1	0.7862 (2)	0.1306 (2)	0.15550 (12)	0.0401 (5)
O2	0.3366 (2)	−0.0447 (2)	0.16381 (16)	0.0681 (6)
H2A	0.2626	0.0017	0.1392	0.102*
O3	0.4671 (2)	0.1695 (2)	0.55717 (12)	0.0556 (5)
Cl1	1.09363 (11)	0.55854 (9)	−0.23667 (5)	0.0747 (3)
Cl2	0.41251 (10)	0.55824 (10)	0.10800 (5)	0.0706 (3)
C21	0.8443 (13)	0.2288 (15)	0.4478 (7)	0.0369 (19)	0.667 (5)
H21A	0.8004	0.2904	0.3983	0.044*	0.667 (5)
H21B	0.8764	0.1400	0.4299	0.044*	0.667 (5)
C22	0.9860 (15)	0.2956 (12)	0.4818 (9)	0.044 (2)	0.667 (5)
H22A	1.0703	0.3027	0.4386	0.053*	0.667 (5)
H22B	0.9558	0.3904	0.4907	0.053*	0.667 (5)
C23	1.0491 (9)	0.2147 (8)	0.5655 (5)	0.0479 (19)	0.667 (5)
H23	1.0836	0.1191	0.5582	0.057*	0.667 (5)
C24	0.9138 (13)	0.2112 (15)	0.6311 (9)	0.049 (2)	0.667 (5)
H24A	0.9507	0.1668	0.6875	0.059*	0.667 (5)
H24B	0.8774	0.3064	0.6354	0.059*	0.667 (5)
C25	0.7790 (15)	0.1296 (10)	0.6030 (5)	0.043 (2)	0.667 (5)
H25A	0.8151	0.0347	0.5977	0.052*	0.667 (5)
H25B	0.6932	0.1240	0.6452	0.052*	0.667 (5)
O4	1.1723 (3)	0.2855 (3)	0.5966 (2)	0.0623 (11)	0.667 (5)
H4	1.2493	0.2861	0.5639	0.093*	0.667 (5)
N2	0.7232 (8)	0.2047 (16)	0.5184 (5)	0.034 (2)	0.667 (5)
C21'	0.850 (3)	0.210 (3)	0.4530 (15)	0.042 (5)	0.333 (5)
H21C	0.8069	0.2460	0.3966	0.051*	0.333 (5)
H21D	0.9095	0.1236	0.4483	0.051*	0.333 (5)
C22'	0.967 (3)	0.318 (3)	0.4775 (18)	0.040 (4)	0.333 (5)
H22C	1.0482	0.3387	0.4333	0.048*	0.333 (5)
H22D	0.9105	0.4054	0.4843	0.048*	0.333 (5)
C23'	1.0410 (17)	0.2493 (16)	0.5636 (10)	0.044 (3)	0.333 (5)
H23'	1.1000	0.3196	0.5883	0.053*	0.333 (5)
C24'	0.915 (3)	0.184 (3)	0.6302 (19)	0.044 (4)	0.333 (5)
H24C	0.9685	0.1185	0.6751	0.053*	0.333 (5)
H24D	0.8646	0.2576	0.6571	0.053*	0.333 (5)
C25'	0.787 (3)	0.105 (2)	0.5893 (10)	0.036 (3)	0.333 (5)
H25C	0.8326	0.0158	0.5781	0.043*	0.333 (5)
H25D	0.7011	0.0843	0.6307	0.043*	0.333 (5)
O4'	1.1380 (7)	0.1335 (6)	0.5593 (4)	0.0532 (19)	0.333 (5)
H4'	1.1397	0.1163	0.5097	0.080*	0.333 (5)
N2'	0.7230 (17)	0.178 (3)	0.5116 (12)	0.034 (4)	0.333 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0315 (12)	0.0437 (14)	0.0382 (13)	0.0044 (10)	0.0024 (10)	0.0000 (10)
C2	0.0428 (14)	0.0448 (14)	0.0359 (13)	0.0018 (11)	−0.0064 (10)	−0.0049 (11)
C3	0.0367 (13)	0.0384 (13)	0.0454 (14)	−0.0061 (10)	−0.0063 (10)	0.0013 (11)
C4	0.0264 (11)	0.0372 (12)	0.0381 (12)	0.0032 (9)	−0.0023 (9)	0.0006 (10)
C5	0.0358 (13)	0.0497 (15)	0.0375 (13)	−0.0078 (11)	−0.0008 (10)	−0.0066 (11)
C6	0.0377 (13)	0.0499 (15)	0.0468 (14)	−0.0137 (11)	0.0038 (11)	−0.0047 (12)
C7	0.0300 (12)	0.0394 (13)	0.0391 (13)	−0.0008 (10)	−0.0044 (10)	0.0003 (10)
C8	0.0323 (13)	0.0430 (14)	0.0540 (15)	0.0056 (10)	−0.0027 (11)	0.0084 (12)
C9	0.0319 (13)	0.0584 (17)	0.0506 (15)	0.0033 (11)	−0.0103 (11)	0.0008 (12)
C10	0.0298 (12)	0.0462 (15)	0.0581 (16)	−0.0023 (10)	0.0036 (11)	−0.0075 (12)
C11	0.0359 (14)	0.0597 (17)	0.0589 (17)	−0.0007 (12)	0.0089 (12)	0.0180 (14)
C12	0.0344 (13)	0.082 (2)	0.0379 (14)	−0.0010 (13)	−0.0006 (11)	0.0131 (13)
C13	0.0474 (15)	0.0620 (18)	0.0423 (14)	−0.0006 (13)	0.0078 (12)	−0.0031 (13)
C14	0.0346 (12)	0.0452 (14)	0.0391 (13)	0.0069 (10)	0.0037 (10)	−0.0038 (11)
C15	0.0391 (13)	0.0524 (16)	0.0441 (14)	−0.0019 (11)	−0.0103 (11)	−0.0096 (12)
C16	0.0398 (13)	0.0411 (14)	0.0455 (14)	−0.0081 (11)	−0.0041 (11)	−0.0031 (11)
C17	0.0282 (11)	0.0429 (13)	0.0326 (12)	−0.0039 (10)	0.0034 (9)	−0.0037 (10)
C18	0.0366 (13)	0.0478 (15)	0.0402 (13)	−0.0089 (11)	−0.0007 (10)	−0.0085 (11)
C19	0.0419 (13)	0.0362 (13)	0.0458 (14)	−0.0024 (10)	0.0060 (11)	−0.0025 (11)
C20	0.0337 (12)	0.0430 (14)	0.0355 (12)	−0.0081 (10)	0.0015 (10)	−0.0027 (10)
C26	0.0471 (15)	0.0555 (17)	0.0517 (16)	0.0108 (13)	−0.0020 (12)	0.0031 (13)
O1	0.0293 (9)	0.0739 (13)	0.0442 (10)	0.0017 (8)	−0.0065 (7)	0.0121 (9)
N1	0.0266 (10)	0.0491 (12)	0.0393 (11)	0.0000 (8)	−0.0023 (8)	0.0093 (9)
O2	0.0403 (11)	0.0565 (12)	0.1079 (18)	−0.0095 (9)	−0.0029 (11)	−0.0127 (12)
O3	0.0340 (9)	0.0783 (13)	0.0472 (10)	−0.0111 (9)	0.0048 (8)	0.0139 (9)
Cl1	0.0836 (6)	0.0706 (5)	0.0591 (5)	0.0037 (4)	0.0180 (4)	0.0208 (4)
Cl2	0.0733 (5)	0.0911 (6)	0.0425 (4)	0.0114 (4)	−0.0080 (3)	0.0028 (4)
C21	0.034 (3)	0.038 (4)	0.037 (3)	0.001 (2)	0.008 (2)	−0.001 (2)
C22	0.029 (3)	0.048 (4)	0.054 (4)	−0.004 (3)	0.006 (2)	−0.001 (3)
C23	0.035 (3)	0.053 (4)	0.055 (3)	−0.002 (2)	−0.0049 (19)	−0.006 (3)
C24	0.040 (3)	0.067 (6)	0.039 (3)	0.001 (3)	−0.009 (2)	−0.003 (3)
C25	0.041 (3)	0.051 (4)	0.034 (3)	0.000 (3)	0.000 (2)	0.005 (3)
O4	0.0366 (16)	0.082 (2)	0.074 (2)	−0.0104 (14)	−0.0054 (13)	−0.0299 (17)
N2	0.029 (2)	0.041 (6)	0.031 (2)	−0.0078 (18)	0.0001 (16)	0.001 (3)
C21'	0.037 (5)	0.054 (9)	0.033 (5)	−0.003 (5)	−0.001 (4)	0.002 (5)
C22'	0.027 (6)	0.047 (6)	0.041 (5)	0.001 (4)	−0.001 (4)	0.005 (4)
C23'	0.032 (5)	0.050 (5)	0.046 (5)	0.005 (3)	−0.004 (3)	0.003 (3)
C24'	0.040 (5)	0.047 (7)	0.043 (5)	0.003 (4)	0.000 (4)	−0.001 (4)
C25'	0.034 (5)	0.037 (5)	0.035 (5)	0.002 (4)	0.009 (4)	0.001 (4)
O4'	0.035 (3)	0.046 (3)	0.075 (4)	0.004 (3)	0.003 (2)	0.000 (3)
N2'	0.038 (5)	0.027 (8)	0.036 (4)	−0.004 (3)	0.002 (3)	−0.002 (4)

C1—C6	1.379 (3)	C18—H18	0.9300
C1—C2	1.380 (3)	C19—H19	0.9300
C1—C13	1.493 (3)	C20—O3	1.233 (3)
C2—C3	1.376 (3)	C20—N2	1.335 (7)
C2—H2	0.9300	C20—N2'	1.359 (14)
C3—C4	1.384 (3)	C26—Cl2	1.793 (3)
C3—H3	0.9300	C26—H26A	0.9700
C4—C5	1.380 (3)	C26—H26B	0.9700
C4—C7	1.495 (3)	O2—H2A	0.8200
C5—C6	1.373 (3)	C21—N2	1.489 (10)
C5—H5	0.9300	C21—C22	1.512 (8)
C6—H6	0.9300	C21—H21A	0.9700
C7—O1	1.235 (3)	C21—H21B	0.9700
C7—N1	1.337 (3)	C22—C23	1.511 (8)
C8—N1	1.461 (3)	C22—H22A	0.9700
C8—C9	1.508 (3)	C22—H22B	0.9700
C8—H8A	0.9700	C23—O4	1.391 (8)
C8—H8B	0.9700	C23—C24	1.521 (9)
C9—C10	1.510 (4)	C23—H23	0.9800
C9—H9A	0.9700	C24—C25	1.505 (8)
C9—H9B	0.9700	C24—H24A	0.9700
C10—O2	1.417 (3)	C24—H24B	0.9700
C10—C11	1.511 (4)	C25—N2	1.483 (9)
C10—H10	0.9800	C25—H25A	0.9700
C11—C12	1.514 (4)	C25—H25B	0.9700
C11—H11A	0.9700	O4—H4	0.8200
C11—H11B	0.9700	C21'—N2'	1.41 (2)
C12—N1	1.460 (3)	C21'—C22'	1.544 (16)
C12—H12A	0.9700	C21'—H21C	0.9700
C12—H12B	0.9700	C21'—H21D	0.9700
C13—Cl1	1.789 (3)	C22'—C23'	1.540 (14)
C13—H13A	0.9700	C22'—H22C	0.9700
C13—H13B	0.9700	C22'—H22D	0.9700
C14—C19	1.384 (3)	C23'—O4'	1.372 (14)
C14—C15	1.385 (4)	C23'—C24'	1.551 (15)
C14—C26	1.496 (3)	C23'—H23'	0.9800
C15—C16	1.373 (3)	C24'—C25'	1.538 (15)
C15—H15	0.9300	C24'—H24C	0.9700
C16—C17	1.383 (3)	C24'—H24D	0.9700
C16—H16	0.9300	C25'—N2'	1.411 (19)
C17—C18	1.380 (3)	C25'—H25C	0.9700
C17—C20	1.496 (3)	C25'—H25D	0.9700
C18—C19	1.380 (3)	O4'—H4'	0.8200
C6—C1—C2	118.6 (2)	N2'—C20—C17	119.6 (8)
C6—C1—C13	120.9 (2)	C14—C26—Cl2	110.88 (18)
C2—C1—C13	120.5 (2)	C14—C26—H26A	109.5
C3—C2—C1	120.8 (2)	Cl2—C26—H26A	109.5
C3—C2—H2	119.6	C14—C26—H26B	109.5
C1—C2—H2	119.6	Cl2—C26—H26B	109.5
C2—C3—C4	120.3 (2)	H26A—C26—H26B	108.1
C2—C3—H3	119.9	C7—N1—C12	120.33 (19)
C4—C3—H3	119.9	C7—N1—C8	125.23 (19)
C5—C4—C3	118.9 (2)	C12—N1—C8	113.28 (19)
C5—C4—C7	119.0 (2)	C10—O2—H2A	109.5
C3—C4—C7	121.8 (2)	N2—C21—C22	108.0 (10)
C6—C5—C4	120.5 (2)	N2—C21—H21A	110.1
C6—C5—H5	119.8	C22—C21—H21A	110.1
C4—C5—H5	119.8	N2—C21—H21B	110.1
C5—C6—C1	120.9 (2)	C22—C21—H21B	110.1
C5—C6—H6	119.5	H21A—C21—H21B	108.4
C1—C6—H6	119.5	C23—C22—C21	113.4 (10)
O1—C7—N1	121.9 (2)	C23—C22—H22A	108.9
O1—C7—C4	119.1 (2)	C21—C22—H22A	108.9
N1—C7—C4	118.95 (19)	C23—C22—H22B	108.9
N1—C8—C9	110.5 (2)	C21—C22—H22B	108.9
N1—C8—H8A	109.6	H22A—C22—H22B	107.7
C9—C8—H8A	109.6	O4—C23—C22	110.9 (6)
N1—C8—H8B	109.6	O4—C23—C24	106.8 (7)
C9—C8—H8B	109.6	C22—C23—C24	106.4 (10)
H8A—C8—H8B	108.1	O4—C23—H23	110.9
C8—C9—C10	111.0 (2)	C22—C23—H23	110.9
C8—C9—H9A	109.4	C24—C23—H23	110.9
C10—C9—H9A	109.4	C25—C24—C23	109.3 (10)
C8—C9—H9B	109.4	C25—C24—H24A	109.8
C10—C9—H9B	109.4	C23—C24—H24A	109.8
H9A—C9—H9B	108.0	C25—C24—H24B	109.8
O2—C10—C11	108.6 (2)	C23—C24—H24B	109.8
O2—C10—C9	112.8 (2)	H24A—C24—H24B	108.3
C11—C10—C9	109.2 (2)	N2—C25—C24	107.6 (10)
O2—C10—H10	108.7	N2—C25—H25A	110.2
C11—C10—H10	108.7	C24—C25—H25A	110.2
C9—C10—H10	108.7	N2—C25—H25B	110.2
C10—C11—C12	111.0 (2)	C24—C25—H25B	110.2
C10—C11—H11A	109.4	H25A—C25—H25B	108.5
C12—C11—H11A	109.4	C23—O4—H4	109.5
C10—C11—H11B	109.4	C20—N2—C25	119.2 (7)
C12—C11—H11B	109.4	C20—N2—C21	122.5 (8)
H11A—C11—H11B	108.0	C25—N2—C21	116.6 (9)
N1—C12—C11	110.3 (2)	N2'—C21'—C22'	115 (2)
N1—C12—H12A	109.6	N2'—C21'—H21C	108.5
C11—C12—H12A	109.6	C22'—C21'—H21C	108.5
N1—C12—H12B	109.6	N2'—C21'—H21D	108.5
C11—C12—H12B	109.6	C22'—C21'—H21D	108.5
H12A—C12—H12B	108.1	H21C—C21'—H21D	107.5
C1—C13—Cl1	111.73 (18)	C23'—C22'—C21'	106 (2)
C1—C13—H13A	109.3	C23'—C22'—H22C	110.6
Cl1—C13—H13A	109.3	C21'—C22'—H22C	110.6
C1—C13—H13B	109.3	C23'—C22'—H22D	110.6
Cl1—C13—H13B	109.3	C21'—C22'—H22D	110.6
H13A—C13—H13B	107.9	H22C—C22'—H22D	108.7
C19—C14—C15	118.6 (2)	O4'—C23'—C22'	115.4 (15)
C19—C14—C26	120.4 (2)	O4'—C23'—C24'	100.2 (15)
C15—C14—C26	121.1 (2)	C22'—C23'—C24'	113 (2)
C16—C15—C14	120.8 (2)	O4'—C23'—H23'	109.4
C16—C15—H15	119.6	C22'—C23'—H23'	109.4
C14—C15—H15	119.6	C24'—C23'—H23'	109.4
C15—C16—C17	120.6 (2)	C25'—C24'—C23'	113 (2)
C15—C16—H16	119.7	C25'—C24'—H24C	109.0
C17—C16—H16	119.7	C23'—C24'—H24C	109.0
C18—C17—C16	119.0 (2)	C25'—C24'—H24D	109.0
C18—C17—C20	121.3 (2)	C23'—C24'—H24D	109.0
C16—C17—C20	119.4 (2)	H24C—C24'—H24D	107.8
C19—C18—C17	120.4 (2)	N2'—C25'—C24'	115 (2)
C19—C18—H18	119.8	N2'—C25'—H25C	108.5
C17—C18—H18	119.8	C24'—C25'—H25C	108.5
C18—C19—C14	120.7 (2)	N2'—C25'—H25D	108.5
C18—C19—H19	119.7	C24'—C25'—H25D	108.5
C14—C19—H19	119.7	H25C—C25'—H25D	107.5
O3—C20—N2	122.4 (4)	C23'—O4'—H4'	109.5
O3—C20—N2'	121.2 (8)	C20—N2'—C21'	129.3 (18)
O3—C20—C17	118.9 (2)	C20—N2'—C25'	122.8 (15)
N2—C20—C17	118.2 (4)	C21'—N2'—C25'	107.6 (19)
C6—C1—C2—C3	1.0 (4)	C19—C14—C26—Cl2	101.6 (3)
C13—C1—C2—C3	179.7 (2)	C15—C14—C26—Cl2	−79.3 (3)
C1—C2—C3—C4	−2.1 (4)	O1—C7—N1—C12	−3.4 (4)
C2—C3—C4—C5	1.4 (4)	C4—C7—N1—C12	173.9 (2)
C2—C3—C4—C7	−172.8 (2)	O1—C7—N1—C8	163.5 (2)
C3—C4—C5—C6	0.3 (4)	C4—C7—N1—C8	−19.2 (4)
C7—C4—C5—C6	174.6 (2)	C11—C12—N1—C7	−135.0 (2)
C4—C5—C6—C1	−1.3 (4)	C11—C12—N1—C8	56.6 (3)
C2—C1—C6—C5	0.6 (4)	C9—C8—N1—C7	135.6 (3)
C13—C1—C6—C5	−178.0 (2)	C9—C8—N1—C12	−56.7 (3)
C5—C4—C7—O1	−52.0 (3)	N2—C21—C22—C23	52.6 (15)
C3—C4—C7—O1	122.2 (3)	C21—C22—C23—O4	−176.1 (9)
C5—C4—C7—N1	130.6 (2)	C21—C22—C23—C24	−60.4 (12)
C3—C4—C7—N1	−55.2 (3)	O4—C23—C24—C25	−177.4 (8)
N1—C8—C9—C10	56.2 (3)	C22—C23—C24—C25	64.1 (11)
C8—C9—C10—O2	−177.3 (2)	C23—C24—C25—N2	−61.6 (13)
C8—C9—C10—C11	−56.4 (3)	O3—C20—N2—C25	−0.8 (16)
O2—C10—C11—C12	179.8 (2)	C17—C20—N2—C25	171.0 (9)
C9—C10—C11—C12	56.4 (3)	O3—C20—N2—C21	163.4 (9)
C10—C11—C12—N1	−56.2 (3)	C17—C20—N2—C21	−24.7 (17)
C6—C1—C13—Cl1	−78.8 (3)	C24—C25—N2—C20	−138.2 (12)
C2—C1—C13—Cl1	102.6 (3)	C24—C25—N2—C21	56.6 (15)
C19—C14—C15—C16	−0.1 (4)	C22—C21—N2—C20	144.2 (14)
C26—C14—C15—C16	−179.2 (2)	C22—C21—N2—C25	−51.2 (16)
C14—C15—C16—C17	−1.3 (4)	N2'—C21'—C22'—C23'	63 (3)
C15—C16—C17—C18	1.3 (4)	C21'—C22'—C23'—O4'	67 (2)
C15—C16—C17—C20	174.8 (2)	C21'—C22'—C23'—C24'	−47 (2)
C16—C17—C18—C19	0.1 (4)	O4'—C23'—C24'—C25'	−82 (2)
C20—C17—C18—C19	−173.3 (2)	C22'—C23'—C24'—C25'	42 (2)
C17—C18—C19—C14	−1.5 (4)	C23'—C24'—C25'—N2'	−46 (3)
C15—C14—C19—C18	1.5 (4)	O3—C20—N2'—C21'	173 (2)
C26—C14—C19—C18	−179.4 (2)	C17—C20—N2'—C21'	−1 (4)
C18—C17—C20—O3	118.4 (3)	O3—C20—N2'—C25'	−15 (4)
C16—C17—C20—O3	−55.0 (3)	C17—C20—N2'—C25'	172 (2)
C18—C17—C20—N2	−53.7 (8)	C22'—C21'—N2'—C20	106 (3)
C16—C17—C20—N2	132.9 (8)	C22'—C21'—N2'—C25'	−68 (3)
C18—C17—C20—N2'	−67.9 (17)	C24'—C25'—N2'—C20	−117 (3)
C16—C17—C20—N2'	118.7 (17)	C24'—C25'—N2'—C21'	57 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	2.18	2.789 (2)	132
O4—H4···O3ii	0.82	2.13	2.793 (3)	138
C11—H11B···O3iii	0.97	2.60	3.522 (3)	160
C26—H26A···O2iv	0.97	2.59	3.494 (4)	154

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AO1i	0.82	2.18	2.789(2)	132
O4H4O3ii	0.82	2.13	2.793(3)	138
C11H11BO3iii	0.97	2.60	3.522(3)	160
C26H26AO2iv	0.97	2.59	3.494(4)	154

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