Methyl 2-[(2-chloro-quinolin-3-yl)(hy-droxy)meth-yl]acrylate.

There are two independent mol-ecules (A and B) in the asymmetric unit of the title compound, C14H12ClNO3. The mean planes of the methyl ester unit (Cmeth-yl-O-C=O; r.m.s. deviation = 0.051 Å for mol-ecule A and 0.016 Å for mol-ecule B) and the chloro-quilonine ring system (r.m.s. deviation = 0.023 Å for mol-ecule A and 0.014 Å for mol-ecule B) form dihedral angles of 63.5 (1)° in mol-ecule A and 78.1 (1)° in mol-ecule B. The main difference between the two independent mol-ecules is reflected in the (H)O-C-C=C(H2) torsion angle which is -109.7 (2)° in mol-ecule A and 10.6 (2)° in mol-ecule B. An intra-molecular O-H⋯O hydrogen bond is observed in mol-ecule A. In the crystal, mol-ecules A and B are linked into pairs via bifurcated O-H⋯(N,Cl) hydrogen bonds and a weak C-H⋯O hydrogen bond links pairs of mol-ecules into chains along [100].

Related literature

For the biological activity of quilonine compounds, see: Biavatti et al. (2002 ▶); Towers et al. (1981 ▶); Shen et al. (1999 ▶). For their luminescent properties, see: Montes et al. (2006 ▶). For applications of acrylate compounds, see: Bhatia et al. (2007 ▶); Sharma (2011 ▶). For conformational aspects of methyl esters, see: Dunitz & Schweizer (1982 ▶). For resonance effects in acrylates, see: Merlino (1971 ▶); Varghese et al. (1986 ▶).

Experimental

Crystal data

C14H12ClNO3

M = 277.70

Triclinic,

a = 9.2614 (4) Å

b = 11.0309 (4) Å

c = 13.8161 (6) Å

α = 102.557 (2)°

β = 100.646 (2)°

γ = 103.704 (2)°

V = 1296.29 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII diffractometer

14402 measured reflections

4466 independent reflections

3767 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.093

S = 1.03

4466 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014050/lh5607sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014050/lh5607Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014050/lh5607Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H12ClNO3	Z = 4
Mr = 277.70	F(000) = 576
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2614 (4) Å	Cell parameters from 4551 reflections
b = 11.0309 (4) Å	θ = 2.0–25.0°
c = 13.8161 (6) Å	µ = 0.30 mm−1
α = 102.557 (2)°	T = 293 K
β = 100.646 (2)°	Block, colourless
γ = 103.704 (2)°	0.35 × 0.30 × 0.25 mm
V = 1296.29 (9) Å3

Bruker SMART APEXII diffractometer	3767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω and φ scans	h = −11→10
14402 measured reflections	k = −12→13
4466 independent reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4048P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4466 reflections	Δρmax = 0.29 e Å−3
344 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (11)

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
Cl1A	0.14491 (5)	0.05724 (5)	0.40164 (4)	0.05417 (16)
O1A	0.36327 (14)	−0.23933 (11)	0.28015 (10)	0.0504 (3)
H1A	0.3051	−0.3109	0.2473	0.076*
O2A	0.05490 (17)	−0.36860 (13)	0.16879 (12)	0.0655 (4)
O3A	−0.03759 (16)	−0.26279 (14)	0.06395 (11)	0.0626 (4)
N1A	0.42615 (15)	0.19802 (13)	0.45982 (10)	0.0356 (3)
C1A	0.33952 (18)	0.08303 (15)	0.40781 (12)	0.0338 (4)
C2A	0.58039 (18)	0.22445 (15)	0.46705 (12)	0.0342 (4)
C3A	0.6764 (2)	0.35052 (17)	0.51704 (13)	0.0443 (4)
H3A	0.6352	0.4153	0.5445	0.053*
C4A	0.8297 (2)	0.37743 (19)	0.52515 (15)	0.0520 (5)
H4A	0.8929	0.4611	0.5583	0.062*
C5A	0.8944 (2)	0.2818 (2)	0.48466 (15)	0.0521 (5)
H5A	0.9999	0.3017	0.4921	0.062*
C6A	0.8037 (2)	0.16025 (19)	0.43468 (14)	0.0456 (4)
H6A	0.8474	0.0973	0.4073	0.055*
C7A	0.64369 (18)	0.12781 (16)	0.42366 (12)	0.0350 (4)
C8A	0.54251 (18)	0.00498 (16)	0.36909 (12)	0.0356 (4)
H8A	0.5817	−0.0604	0.3401	0.043*
C9A	0.38875 (18)	−0.02014 (15)	0.35779 (12)	0.0321 (3)
C10A	0.27692 (18)	−0.14936 (15)	0.29730 (12)	0.0352 (4)
H10A	0.2067	−0.1775	0.3385	0.042*
C11A	0.18355 (18)	−0.14703 (15)	0.19609 (12)	0.0368 (4)
C12A	0.2087 (2)	−0.05086 (19)	0.15361 (15)	0.0547 (5)
H12A	0.1496	−0.0596	0.0889	0.066*
H12B	0.2855	0.0259	0.1883	0.066*
C13A	0.0617 (2)	−0.27074 (17)	0.14275 (14)	0.0433 (4)
C14A	−0.1553 (3)	−0.3815 (2)	0.00547 (18)	0.0770 (7)
H14A	−0.2208	−0.3645	−0.0494	0.116*
H14B	−0.2151	−0.4134	0.0493	0.116*
H14C	−0.1082	−0.4451	−0.0223	0.116*
Cl1B	0.34205 (5)	0.35070 (5)	0.27784 (4)	0.05394 (16)
N1B	0.52758 (16)	0.22798 (12)	0.21855 (10)	0.0386 (3)
O1B	0.71157 (13)	0.63179 (11)	0.42717 (8)	0.0422 (3)
H1B	0.7063	0.7033	0.4560	0.063*
O2B	0.45974 (15)	0.56659 (12)	0.12824 (10)	0.0530 (3)
O3B	0.59711 (17)	0.75707 (12)	0.11953 (9)	0.0553 (4)
C1B	0.51958 (18)	0.34408 (15)	0.25490 (12)	0.0342 (4)
C2B	0.66394 (19)	0.21585 (15)	0.19986 (12)	0.0357 (4)
C3B	0.6778 (2)	0.09090 (17)	0.16220 (14)	0.0482 (5)
H3B	0.5944	0.0184	0.1500	0.058*
C4B	0.8116 (3)	0.07581 (18)	0.14373 (16)	0.0560 (5)
H4B	0.8196	−0.0072	0.1191	0.067*
C5B	0.9382 (3)	0.1835 (2)	0.16113 (18)	0.0607 (6)
H5B	1.0297	0.1717	0.1483	0.073*
C6B	0.9281 (2)	0.30528 (18)	0.19672 (16)	0.0532 (5)
H6B	1.0125	0.3764	0.2074	0.064*
C7B	0.79075 (19)	0.32456 (15)	0.21766 (13)	0.0369 (4)
C8B	0.77249 (18)	0.44774 (15)	0.25652 (12)	0.0364 (4)
H8B	0.8541	0.5215	0.2686	0.044*
C9B	0.63788 (17)	0.46076 (14)	0.27667 (11)	0.0316 (3)
C10B	0.62325 (18)	0.59300 (14)	0.32479 (12)	0.0328 (4)
H10B	0.5155	0.5844	0.3250	0.039*
C11B	0.67326 (18)	0.68846 (14)	0.26558 (12)	0.0335 (4)
C12B	0.7998 (2)	0.78554 (17)	0.29927 (15)	0.0470 (4)
H12C	0.8246	0.8416	0.2595	0.056*
H12D	0.8646	0.7982	0.3629	0.056*
C13B	0.5651 (2)	0.66278 (15)	0.16500 (13)	0.0375 (4)
C14B	0.4924 (3)	0.7379 (2)	0.02265 (16)	0.0765 (7)
H14D	0.5241	0.8104	−0.0041	0.115*
H14E	0.3909	0.7304	0.0321	0.115*
H14F	0.4924	0.6599	−0.0246	0.115*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0291 (2)	0.0501 (3)	0.0697 (3)	0.00871 (19)	0.0111 (2)	−0.0073 (2)
O1A	0.0485 (7)	0.0334 (6)	0.0626 (8)	0.0161 (6)	0.0061 (6)	0.0011 (6)
O2A	0.0628 (9)	0.0374 (8)	0.0763 (10)	−0.0048 (6)	0.0039 (8)	0.0076 (7)
O3A	0.0484 (8)	0.0571 (9)	0.0545 (8)	−0.0067 (6)	−0.0094 (7)	0.0015 (7)
N1A	0.0342 (7)	0.0321 (7)	0.0354 (7)	0.0073 (6)	0.0065 (6)	0.0029 (6)
C1A	0.0290 (8)	0.0363 (9)	0.0329 (8)	0.0085 (7)	0.0059 (7)	0.0052 (7)
C2A	0.0332 (9)	0.0356 (9)	0.0300 (8)	0.0054 (7)	0.0042 (7)	0.0093 (7)
C3A	0.0472 (11)	0.0356 (9)	0.0436 (10)	0.0040 (8)	0.0095 (8)	0.0079 (8)
C4A	0.0425 (11)	0.0462 (11)	0.0518 (11)	−0.0086 (9)	0.0031 (9)	0.0129 (9)
C5A	0.0308 (9)	0.0623 (13)	0.0565 (12)	0.0009 (9)	0.0039 (8)	0.0225 (10)
C6A	0.0335 (9)	0.0544 (11)	0.0499 (11)	0.0135 (8)	0.0089 (8)	0.0166 (9)
C7A	0.0326 (8)	0.0394 (9)	0.0323 (8)	0.0097 (7)	0.0046 (7)	0.0122 (7)
C8A	0.0359 (9)	0.0357 (9)	0.0355 (9)	0.0129 (7)	0.0089 (7)	0.0075 (7)
C9A	0.0322 (8)	0.0316 (8)	0.0301 (8)	0.0085 (7)	0.0063 (6)	0.0057 (6)
C10A	0.0358 (9)	0.0288 (8)	0.0383 (9)	0.0085 (7)	0.0101 (7)	0.0042 (7)
C11A	0.0329 (9)	0.0328 (9)	0.0377 (9)	0.0039 (7)	0.0079 (7)	0.0024 (7)
C12A	0.0561 (12)	0.0461 (11)	0.0455 (11)	−0.0004 (9)	−0.0049 (9)	0.0104 (9)
C13A	0.0383 (10)	0.0398 (10)	0.0422 (10)	0.0030 (8)	0.0108 (8)	−0.0001 (8)
C14A	0.0527 (13)	0.0717 (15)	0.0651 (14)	−0.0098 (11)	−0.0082 (11)	−0.0158 (12)
Cl1B	0.0352 (2)	0.0458 (3)	0.0787 (4)	0.0054 (2)	0.0187 (2)	0.0156 (2)
N1B	0.0413 (8)	0.0290 (7)	0.0403 (8)	0.0030 (6)	0.0077 (6)	0.0087 (6)
O1B	0.0493 (7)	0.0388 (7)	0.0343 (6)	0.0170 (6)	0.0034 (5)	0.0026 (5)
O2B	0.0555 (8)	0.0369 (7)	0.0473 (7)	0.0006 (6)	−0.0073 (6)	0.0035 (6)
O3B	0.0787 (10)	0.0391 (7)	0.0404 (7)	0.0100 (7)	0.0008 (6)	0.0144 (6)
C1B	0.0328 (8)	0.0326 (9)	0.0348 (9)	0.0054 (7)	0.0058 (7)	0.0110 (7)
C2B	0.0450 (10)	0.0278 (8)	0.0326 (8)	0.0078 (7)	0.0078 (7)	0.0093 (7)
C3B	0.0625 (12)	0.0281 (9)	0.0502 (11)	0.0083 (8)	0.0157 (9)	0.0068 (8)
C4B	0.0755 (14)	0.0349 (10)	0.0615 (13)	0.0233 (10)	0.0231 (11)	0.0080 (9)
C5B	0.0591 (13)	0.0498 (12)	0.0796 (15)	0.0261 (10)	0.0275 (11)	0.0107 (11)
C6B	0.0438 (11)	0.0393 (10)	0.0747 (14)	0.0113 (8)	0.0193 (10)	0.0088 (9)
C7B	0.0401 (9)	0.0314 (8)	0.0385 (9)	0.0105 (7)	0.0092 (7)	0.0085 (7)
C8B	0.0337 (9)	0.0264 (8)	0.0430 (9)	0.0032 (7)	0.0061 (7)	0.0065 (7)
C9B	0.0330 (8)	0.0287 (8)	0.0307 (8)	0.0065 (7)	0.0044 (7)	0.0090 (6)
C10B	0.0308 (8)	0.0291 (8)	0.0348 (9)	0.0074 (6)	0.0047 (7)	0.0051 (7)
C11B	0.0350 (9)	0.0252 (8)	0.0367 (9)	0.0089 (7)	0.0063 (7)	0.0033 (7)
C12B	0.0444 (10)	0.0370 (10)	0.0510 (11)	0.0017 (8)	0.0039 (8)	0.0124 (8)
C13B	0.0450 (10)	0.0274 (8)	0.0376 (9)	0.0121 (8)	0.0072 (8)	0.0047 (7)
C14B	0.115 (2)	0.0619 (14)	0.0432 (12)	0.0268 (14)	−0.0072 (12)	0.0172 (10)

Cl1A—C1A	1.7396 (16)	Cl1B—C1B	1.7459 (17)
O1A—C10A	1.4228 (19)	N1B—C1B	1.295 (2)
O1A—H1A	0.8200	N1B—C2B	1.366 (2)
O2A—C13A	1.202 (2)	O1B—C10B	1.4130 (18)
O3A—C13A	1.322 (2)	O1B—H1B	0.8200
O3A—C14A	1.447 (2)	O2B—C13B	1.195 (2)
N1A—C1A	1.295 (2)	O3B—C13B	1.331 (2)
N1A—C2A	1.369 (2)	O3B—C14B	1.441 (2)
C1A—C9A	1.415 (2)	C1B—C9B	1.410 (2)
C2A—C3A	1.404 (2)	C2B—C7B	1.406 (2)
C2A—C7A	1.410 (2)	C2B—C3B	1.408 (2)
C3A—C4A	1.358 (3)	C3B—C4B	1.351 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.397 (3)	C4B—C5B	1.399 (3)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.353 (3)	C5B—C6B	1.358 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.410 (2)	C6B—C7B	1.409 (2)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.406 (2)	C7B—C8B	1.410 (2)
C8A—C9A	1.357 (2)	C8B—C9B	1.359 (2)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.505 (2)	C9B—C10B	1.514 (2)
C10A—C11A	1.511 (2)	C10B—C11B	1.509 (2)
C10A—H10A	0.9800	C10B—H10B	0.9800
C11A—C12A	1.315 (3)	C11B—C12B	1.313 (2)
C11A—C13A	1.485 (2)	C11B—C13B	1.481 (2)
C12A—H12A	0.9300	C12B—H12C	0.9300
C12A—H12B	0.9300	C12B—H12D	0.9300
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C10A—O1A—H1A	109.5	C1B—N1B—C2B	117.42 (14)
C13A—O3A—C14A	116.51 (17)	C10B—O1B—H1B	109.5
C1A—N1A—C2A	117.75 (14)	C13B—O3B—C14B	115.36 (15)
N1A—C1A—C9A	126.31 (15)	N1B—C1B—C9B	126.51 (15)
N1A—C1A—Cl1A	115.01 (12)	N1B—C1B—Cl1B	114.43 (12)
C9A—C1A—Cl1A	118.68 (12)	C9B—C1B—Cl1B	119.06 (12)
N1A—C2A—C3A	119.28 (15)	N1B—C2B—C7B	121.77 (14)
N1A—C2A—C7A	121.07 (14)	N1B—C2B—C3B	119.00 (15)
C3A—C2A—C7A	119.64 (15)	C7B—C2B—C3B	119.23 (16)
C4A—C3A—C2A	119.69 (18)	C4B—C3B—C2B	120.34 (18)
C4A—C3A—H3A	120.2	C4B—C3B—H3B	119.8
C2A—C3A—H3A	120.2	C2B—C3B—H3B	119.8
C3A—C4A—C5A	121.23 (17)	C3B—C4B—C5B	120.76 (17)
C3A—C4A—H4A	119.4	C3B—C4B—H4B	119.6
C5A—C4A—H4A	119.4	C5B—C4B—H4B	119.6
C6A—C5A—C4A	120.03 (17)	C6B—C5B—C4B	120.30 (19)
C6A—C5A—H5A	120.0	C6B—C5B—H5B	119.9
C4A—C5A—H5A	120.0	C4B—C5B—H5B	119.9
C5A—C6A—C7A	120.83 (18)	C5B—C6B—C7B	120.46 (18)
C5A—C6A—H6A	119.6	C5B—C6B—H6B	119.8
C7A—C6A—H6A	119.6	C7B—C6B—H6B	119.8
C8A—C7A—C6A	123.60 (16)	C2B—C7B—C8B	117.38 (15)
C8A—C7A—C2A	117.83 (15)	C2B—C7B—C6B	118.91 (15)
C6A—C7A—C2A	118.54 (15)	C8B—C7B—C6B	123.71 (16)
C9A—C8A—C7A	121.35 (15)	C9B—C8B—C7B	121.30 (15)
C9A—C8A—H8A	119.3	C9B—C8B—H8B	119.3
C7A—C8A—H8A	119.3	C7B—C8B—H8B	119.3
C8A—C9A—C1A	115.59 (14)	C8B—C9B—C1B	115.61 (14)
C8A—C9A—C10A	122.69 (14)	C8B—C9B—C10B	120.66 (14)
C1A—C9A—C10A	121.72 (14)	C1B—C9B—C10B	123.64 (14)
O1A—C10A—C9A	107.26 (13)	O1B—C10B—C11B	112.74 (13)
O1A—C10A—C11A	109.72 (13)	O1B—C10B—C9B	106.54 (12)
C9A—C10A—C11A	113.64 (13)	C11B—C10B—C9B	111.38 (13)
O1A—C10A—H10A	108.7	O1B—C10B—H10B	108.7
C9A—C10A—H10A	108.7	C11B—C10B—H10B	108.7
C11A—C10A—H10A	108.7	C9B—C10B—H10B	108.7
C12A—C11A—C13A	121.29 (16)	C12B—C11B—C13B	122.74 (16)
C12A—C11A—C10A	125.54 (15)	C12B—C11B—C10B	123.77 (15)
C13A—C11A—C10A	113.06 (14)	C13B—C11B—C10B	113.50 (13)
C11A—C12A—H12A	120.0	C11B—C12B—H12C	120.0
C11A—C12A—H12B	120.0	C11B—C12B—H12D	120.0
H12A—C12A—H12B	120.0	H12C—C12B—H12D	120.0
O2A—C13A—O3A	123.47 (17)	O2B—C13B—O3B	123.36 (15)
O2A—C13A—C11A	122.95 (17)	O2B—C13B—C11B	123.22 (15)
O3A—C13A—C11A	113.58 (16)	O3B—C13B—C11B	113.42 (14)
O3A—C14A—H14A	109.5	O3B—C14B—H14D	109.5
O3A—C14A—H14B	109.5	O3B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
O3A—C14A—H14C	109.5	O3B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C2A—N1A—C1A—C9A	0.7 (2)	C2B—N1B—C1B—C9B	0.6 (2)
C2A—N1A—C1A—Cl1A	−179.69 (11)	C2B—N1B—C1B—Cl1B	−179.34 (11)
C1A—N1A—C2A—C3A	175.82 (15)	C1B—N1B—C2B—C7B	−0.9 (2)
C1A—N1A—C2A—C7A	−3.1 (2)	C1B—N1B—C2B—C3B	178.77 (15)
N1A—C2A—C3A—C4A	179.57 (16)	N1B—C2B—C3B—C4B	−179.50 (17)
C7A—C2A—C3A—C4A	−1.5 (2)	C7B—C2B—C3B—C4B	0.2 (3)
C2A—C3A—C4A—C5A	0.0 (3)	C2B—C3B—C4B—C5B	−0.3 (3)
C3A—C4A—C5A—C6A	1.2 (3)	C3B—C4B—C5B—C6B	−0.2 (3)
C4A—C5A—C6A—C7A	−0.7 (3)	C4B—C5B—C6B—C7B	0.7 (3)
C5A—C6A—C7A—C8A	177.30 (17)	N1B—C2B—C7B—C8B	0.4 (2)
C5A—C6A—C7A—C2A	−0.8 (3)	C3B—C2B—C7B—C8B	−179.26 (15)
N1A—C2A—C7A—C8A	2.6 (2)	N1B—C2B—C7B—C6B	−179.98 (16)
C3A—C2A—C7A—C8A	−176.31 (15)	C3B—C2B—C7B—C6B	0.3 (2)
N1A—C2A—C7A—C6A	−179.18 (15)	C5B—C6B—C7B—C2B	−0.8 (3)
C3A—C2A—C7A—C6A	1.9 (2)	C5B—C6B—C7B—C8B	178.76 (19)
C6A—C7A—C8A—C9A	−177.76 (16)	C2B—C7B—C8B—C9B	0.5 (2)
C2A—C7A—C8A—C9A	0.4 (2)	C6B—C7B—C8B—C9B	−179.11 (17)
C7A—C8A—C9A—C1A	−2.5 (2)	C7B—C8B—C9B—C1B	−0.8 (2)
C7A—C8A—C9A—C10A	178.19 (15)	C7B—C8B—C9B—C10B	176.02 (14)
N1A—C1A—C9A—C8A	2.1 (2)	N1B—C1B—C9B—C8B	0.3 (2)
Cl1A—C1A—C9A—C8A	−177.49 (12)	Cl1B—C1B—C9B—C8B	−179.82 (12)
N1A—C1A—C9A—C10A	−178.61 (16)	N1B—C1B—C9B—C10B	−176.42 (15)
Cl1A—C1A—C9A—C10A	1.8 (2)	Cl1B—C1B—C9B—C10B	3.5 (2)
C8A—C9A—C10A—O1A	14.0 (2)	C8B—C9B—C10B—O1B	−70.40 (18)
C1A—C9A—C10A—O1A	−165.25 (14)	C1B—C9B—C10B—O1B	106.14 (16)
C8A—C9A—C10A—C11A	−107.46 (17)	C8B—C9B—C10B—C11B	52.92 (19)
C1A—C9A—C10A—C11A	73.3 (2)	C1B—C9B—C10B—C11B	−130.54 (15)
O1A—C10A—C11A—C12A	−109.7 (2)	O1B—C10B—C11B—C12B	10.6 (2)
C9A—C10A—C11A—C12A	10.4 (2)	C9B—C10B—C11B—C12B	−109.15 (18)
O1A—C10A—C11A—C13A	66.52 (18)	O1B—C10B—C11B—C13B	−169.19 (12)
C9A—C10A—C11A—C13A	−173.42 (13)	C9B—C10B—C11B—C13B	71.10 (17)
C14A—O3A—C13A—O2A	−2.5 (3)	C14B—O3B—C13B—O2B	1.8 (3)
C14A—O3A—C13A—C11A	177.18 (17)	C14B—O3B—C13B—C11B	−178.39 (16)
C12A—C11A—C13A—O2A	164.7 (2)	C12B—C11B—C13B—O2B	170.78 (18)
C10A—C11A—C13A—O2A	−11.7 (2)	C10B—C11B—C13B—O2B	−9.5 (2)
C12A—C11A—C13A—O3A	−15.0 (3)	C12B—C11B—C13B—O3B	−9.0 (2)
C10A—C11A—C13A—O3A	168.60 (15)	C10B—C11B—C13B—O3B	170.72 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2A	0.82	2.24	2.8372 (19)	130
O1B—H1B···Cl1Ai	0.82	2.79	3.5040 (12)	147
O1B—H1B···N1Ai	0.82	2.16	2.8609 (17)	144
C5A—H5A···O1Bii	0.93	2.56	3.451 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2A	0.82	2.24	2.8372 (19)	130
O1B—H1B⋯Cl1A i	0.82	2.79	3.5040 (12)	147
O1B—H1B⋯N1A i	0.82	2.16	2.8609 (17)	144
C5A—H5A⋯O1B ii	0.93	2.56	3.451 (2)	162

Symmetry codes: (i) ; (ii) .