Z′ = 4 structure without obvious pseudosymmetry: implications for the formation of solid-state compounds

Crystals of 4-chloro-2′-biphenylol grown at 263 K and studied at both 293 and 142 K are loosely packed and contain OH...O bonded tetramers composed of four crystallographically independent molecules (Z′ = 4). Approximate symmetry relationships between independent molecules are apparent in many, perhaps even most, structures with Z′ > 1, but are not obvious in this structure. The inefficient crystal packing, the surprisingly large value of Z′ and the absence of pseudosymmetry reflect the difficulty of finding a dense molecular arrangement that also allows for hydrogen-bond formation. Impediments to good packing are the steric congestion around the ortho hydroxyl groups and the difficulty in filling space with significantly twisted biphenyl fragments. The packing arrangement adopted is strongly reminiscent of the structure type found for eight simple 4,4′-biphenyl derivatives, but one of the four independent 4-chloro-2′-biphenylol molecules has an orientation that is significantly different from the orientations of the other three and that does not fit the 4,4′-XPhPhY pattern. It is suggested that molecules that crystallize with Z′ > 1 are good candidates for solid-state compound formation.

Computing details

For both compounds, data collection: COLLECT software (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997). Program(s) used to solve structure: From structure at 142 K for k00209; SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998) for k00201. For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL PC (Sheldrick, 1990).

(k00209) 4-chloro-2'-biphenylol

Crystal data

C12H9ClO	Dx = 1.316 Mg m^−3
Mr = 204.64	Melting point: 41-43_C K
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
a = 17.418 (3) Å	Cell parameters from 33500 reflections
b = 12.015 (2) Å	θ = 1.0–25.0°
c = 19.841 (3) Å	µ = 0.33 mm^−1
β = 95.59 (2)°	T = 293 K
V = 4132.5 (12) Å^3	Pointed laths elongated along b. Crystals are thinnest in direction a*., colourless
Z = 16	0.26 × 0.25 × 0.05 mm
F(000) = 1696

Data collection

Nonius Kappa-CCD diffractometer	7262 independent reflections
Radiation source: fine-focus sealed tube	4186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 1.2°
ω scans with 1.0° steps at χ=55°	h = 0→20
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = 0→14
Tmin = 0.92, Tmax = 0.98	l = −23→23
9897 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
7262 reflections	Δρmax = 0.30 e Å^−3
510 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (4)

Special details

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 4; the total number of frames measured was 463.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
ClA	0.85484 (5)	0.67339 (6)	0.65174 (4)	0.1117 (3)
OA	0.82138 (9)	0.14113 (12)	0.56904 (7)	0.0643 (4)
HA	0.8092	0.0895	0.5432	0.096*
C1A	0.88198 (12)	0.30034 (19)	0.66579 (11)	0.0551 (6)
C2A	0.85701 (13)	0.3622 (2)	0.71853 (12)	0.0679 (7)
H2A	0.8461	0.3258	0.7578	0.081*
C3A	0.84788 (14)	0.4762 (2)	0.71436 (14)	0.0747 (7)
H3A	0.8306	0.5158	0.7502	0.090*
C4A	0.86455 (14)	0.5300 (2)	0.65682 (15)	0.0697 (7)
C5A	0.88845 (14)	0.4719 (2)	0.60351 (14)	0.0766 (7)
H5A	0.8992	0.5090	0.5644	0.092*
C6A	0.89667 (13)	0.3573 (2)	0.60800 (12)	0.0674 (7)
H6A	0.9124	0.3181	0.5714	0.081*
C7A	0.89540 (12)	0.17904 (19)	0.67347 (12)	0.0538 (6)
C8A	0.86755 (12)	0.1015 (2)	0.62479 (12)	0.0545 (6)
C9A	0.88242 (13)	−0.0097 (2)	0.63310 (14)	0.0693 (7)
H9A	0.8637	−0.0598	0.5997	0.083*
C10A	0.92506 (14)	−0.0479 (2)	0.69077 (15)	0.0758 (8)
H10A	0.9356	−0.1234	0.6959	0.091*
C11A	0.95187 (13)	0.0254 (2)	0.74035 (14)	0.0762 (7)
H11A	0.9796	0.0000	0.7798	0.091*
C12A	0.93723 (13)	0.1377 (2)	0.73110 (12)	0.0654 (7)
H12A	0.9561	0.1873	0.7647	0.079*
ClB	0.91162 (5)	0.40671 (5)	0.41143 (4)	0.1211 (4)
OB	0.75176 (8)	−0.05057 (11)	0.49362 (8)	0.0592 (4)
HB	0.7191	−0.0839	0.5128	0.089*
C1B	0.86573 (14)	0.03780 (17)	0.41839 (10)	0.0527 (6)
C2B	0.93952 (15)	0.0808 (2)	0.43334 (12)	0.0723 (7)
H2B	0.9803	0.0326	0.4453	0.087*
C3B	0.95338 (16)	0.1945 (2)	0.43077 (13)	0.0835 (8)
H3B	1.0028	0.2225	0.4418	0.100*
C4B	0.8938 (2)	0.2645 (2)	0.41200 (13)	0.0749 (8)
C5B	0.82097 (17)	0.2245 (2)	0.39443 (12)	0.0715 (7)
H5B	0.7810	0.2731	0.3804	0.086*
C6B	0.80720 (14)	0.11175 (19)	0.39775 (11)	0.0593 (6)
H6B	0.7577	0.0849	0.3859	0.071*
C7B	0.85245 (12)	−0.08364 (17)	0.42397 (11)	0.0528 (6)
C8B	0.79507 (12)	−0.12604 (19)	0.46092 (11)	0.0512 (6)
C9B	0.78386 (14)	−0.2384 (2)	0.46703 (12)	0.0678 (7)
H9B	0.7456	−0.2648	0.4925	0.081*
C10B	0.82926 (17)	−0.3120 (2)	0.43551 (15)	0.0858 (8)
H10B	0.8211	−0.3882	0.4389	0.103*
C11B	0.88659 (17)	−0.2727 (2)	0.39912 (15)	0.0885 (8)
H11B	0.9176	−0.3223	0.3781	0.106*
C12B	0.89826 (14)	−0.1599 (2)	0.39370 (13)	0.0723 (7)
H12B	0.9376	−0.1343	0.3693	0.087*
ClC	0.71821 (4)	−0.60374 (5)	0.49097 (4)	0.0893 (3)
OC	0.63907 (8)	−0.09850 (10)	0.58749 (7)	0.0569 (4)
HC	0.6510	−0.0381	0.6047	0.085*
C1C	0.57713 (12)	−0.30106 (17)	0.53323 (11)	0.0506 (6)
C2C	0.56921 (14)	−0.35276 (19)	0.47045 (13)	0.0724 (7)
H2C	0.5343	−0.3241	0.4364	0.087*
C3C	0.61171 (15)	−0.4455 (2)	0.45741 (13)	0.0763 (8)
H3C	0.6056	−0.4789	0.4149	0.092*
C4C	0.66295 (13)	−0.48801 (17)	0.50730 (14)	0.0609 (7)
C5C	0.67181 (13)	−0.43963 (18)	0.57033 (13)	0.0614 (6)
H5C	0.7060	−0.4698	0.6044	0.074*
C6C	0.62954 (13)	−0.34593 (17)	0.58265 (12)	0.0561 (6)
H6C	0.6364	−0.3123	0.6250	0.067*
C7C	0.52864 (13)	−0.20295 (17)	0.54702 (10)	0.0484 (5)
C8C	0.55993 (13)	−0.10534 (18)	0.57536 (10)	0.0473 (6)
C9C	0.51253 (14)	−0.01696 (17)	0.58855 (10)	0.0549 (6)
H9C	0.5337	0.0477	0.6082	0.066*
C10C	0.43371 (15)	−0.0249 (2)	0.57243 (11)	0.0631 (7)
H10C	0.4020	0.0344	0.5814	0.076*
C11C	0.40211 (14)	−0.1202 (2)	0.54318 (12)	0.0654 (7)
H11C	0.3492	−0.1251	0.5316	0.079*
C12C	0.44922 (14)	−0.20761 (19)	0.53124 (11)	0.0603 (6)
H12C	0.4274	−0.2722	0.5120	0.072*
ClD	0.66916 (6)	−0.35465 (6)	0.79339 (4)	0.1305 (4)
OD	0.69011 (9)	0.10990 (11)	0.63611 (8)	0.0667 (5)
HD	0.7173	0.1435	0.6114	0.100*
C1D	0.64938 (15)	0.01482 (19)	0.75631 (11)	0.0585 (6)
C2D	0.58515 (15)	−0.0481 (2)	0.76658 (12)	0.0729 (7)
H2D	0.5372	−0.0137	0.7657	0.088*
C3D	0.59100 (19)	−0.1617 (3)	0.77813 (13)	0.0869 (8)
H3D	0.5474	−0.2035	0.7846	0.104*
C4D	0.6620 (2)	−0.2113 (2)	0.77984 (12)	0.0817 (8)
C5D	0.72583 (19)	−0.1517 (3)	0.76991 (14)	0.0895 (9)
H5D	0.7736	−0.1866	0.7710	0.107*
C6D	0.71960 (15)	−0.0398 (2)	0.75823 (12)	0.0758 (7)
H6D	0.7637	0.0008	0.7514	0.091*
C7D	0.64317 (12)	0.13641 (19)	0.74252 (12)	0.0552 (6)
C8D	0.66481 (12)	0.18256 (19)	0.68313 (12)	0.0540 (6)
C9D	0.65952 (13)	0.2945 (2)	0.66976 (13)	0.0715 (7)
H9D	0.6743	0.3230	0.6294	0.086*
C10D	0.63201 (16)	0.3643 (2)	0.71710 (17)	0.0881 (9)
H10D	0.6283	0.4403	0.7086	0.106*
C11D	0.61029 (16)	0.3227 (2)	0.77593 (16)	0.0922 (9)
H11D	0.5920	0.3703	0.8077	0.111*
C12D	0.61524 (14)	0.2094 (2)	0.78875 (12)	0.0804 (8)
H12D	0.5996	0.1817	0.8290	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
ClA	0.1242 (7)	0.0714 (5)	0.1340 (7)	−0.0102 (4)	−0.0148 (5)	−0.0007 (4)
OA	0.0635 (10)	0.0786 (10)	0.0501 (11)	−0.0007 (9)	0.0015 (9)	−0.0116 (8)
C1A	0.0462 (14)	0.0723 (17)	0.0465 (16)	−0.0076 (12)	0.0040 (12)	−0.0029 (14)
C2A	0.0715 (18)	0.0758 (18)	0.0576 (17)	−0.0073 (14)	0.0122 (14)	−0.0062 (14)
C3A	0.0712 (18)	0.0787 (19)	0.074 (2)	−0.0034 (15)	0.0077 (15)	−0.0190 (16)
C4A	0.0634 (18)	0.0648 (17)	0.078 (2)	−0.0094 (13)	−0.0078 (16)	−0.0036 (16)
C5A	0.0778 (19)	0.083 (2)	0.068 (2)	−0.0172 (16)	0.0010 (15)	0.0104 (17)
C6A	0.0680 (17)	0.0820 (19)	0.0524 (17)	−0.0078 (14)	0.0072 (13)	−0.0070 (14)
C7A	0.0454 (14)	0.0712 (17)	0.0452 (15)	−0.0006 (13)	0.0057 (12)	−0.0035 (14)
C8A	0.0419 (14)	0.0733 (18)	0.0488 (16)	0.0052 (13)	0.0072 (12)	−0.0055 (14)
C9A	0.0587 (17)	0.0761 (19)	0.072 (2)	0.0096 (14)	0.0017 (15)	−0.0178 (15)
C10A	0.0679 (18)	0.0722 (18)	0.086 (2)	0.0123 (15)	0.0026 (16)	−0.0088 (18)
C11A	0.0609 (17)	0.091 (2)	0.075 (2)	0.0110 (16)	−0.0041 (14)	0.0041 (18)
C12A	0.0603 (17)	0.0789 (19)	0.0561 (18)	−0.0043 (14)	0.0005 (14)	−0.0102 (14)
ClB	0.1854 (9)	0.0639 (5)	0.1273 (7)	−0.0200 (5)	0.0827 (7)	−0.0062 (4)
OB	0.0547 (10)	0.0619 (9)	0.0645 (11)	−0.0002 (8)	0.0225 (8)	−0.0056 (8)
C1B	0.0532 (16)	0.0568 (15)	0.0511 (15)	0.0023 (14)	0.0196 (12)	−0.0004 (12)
C2B	0.0629 (19)	0.0690 (18)	0.088 (2)	0.0046 (15)	0.0234 (15)	0.0087 (14)
C3B	0.079 (2)	0.084 (2)	0.093 (2)	−0.0199 (18)	0.0355 (17)	−0.0056 (17)
C4B	0.102 (2)	0.0597 (17)	0.0701 (19)	−0.0024 (18)	0.0469 (18)	−0.0027 (14)
C5B	0.088 (2)	0.0683 (19)	0.0622 (17)	0.0194 (16)	0.0290 (16)	0.0053 (14)
C6B	0.0629 (16)	0.0611 (16)	0.0561 (16)	0.0094 (14)	0.0171 (13)	0.0020 (12)
C7B	0.0489 (15)	0.0583 (15)	0.0520 (15)	0.0091 (13)	0.0090 (12)	0.0008 (12)
C8B	0.0463 (14)	0.0576 (15)	0.0498 (15)	0.0040 (12)	0.0044 (12)	−0.0008 (12)
C9B	0.0738 (17)	0.0626 (17)	0.0684 (17)	−0.0056 (14)	0.0145 (14)	−0.0004 (14)
C10B	0.099 (2)	0.0555 (16)	0.105 (2)	0.0056 (16)	0.0208 (19)	−0.0035 (16)
C11B	0.094 (2)	0.066 (2)	0.109 (2)	0.0221 (16)	0.0293 (19)	−0.0125 (17)
C12B	0.0691 (17)	0.0678 (18)	0.0840 (19)	0.0115 (14)	0.0272 (14)	−0.0019 (15)
ClC	0.0763 (5)	0.0640 (4)	0.1302 (7)	0.0049 (3)	0.0227 (4)	−0.0253 (4)
OC	0.0545 (11)	0.0545 (9)	0.0623 (11)	−0.0031 (7)	0.0088 (8)	−0.0125 (8)
C1C	0.0517 (14)	0.0506 (13)	0.0492 (15)	−0.0054 (12)	0.0039 (12)	0.0010 (12)
C2C	0.0851 (19)	0.0705 (17)	0.0578 (18)	0.0122 (15)	−0.0119 (14)	−0.0072 (14)
C3C	0.091 (2)	0.0721 (18)	0.0640 (18)	0.0087 (16)	−0.0019 (16)	−0.0244 (15)
C4C	0.0556 (16)	0.0489 (14)	0.079 (2)	−0.0030 (12)	0.0095 (15)	−0.0108 (14)
C5C	0.0599 (16)	0.0507 (14)	0.0720 (19)	0.0010 (12)	−0.0014 (14)	0.0044 (14)
C6C	0.0644 (16)	0.0517 (14)	0.0513 (15)	−0.0009 (13)	0.0016 (13)	−0.0038 (12)
C7C	0.0504 (15)	0.0511 (14)	0.0443 (14)	0.0006 (12)	0.0077 (11)	0.0035 (11)
C8C	0.0465 (15)	0.0598 (15)	0.0374 (13)	0.0019 (13)	0.0130 (11)	0.0037 (11)
C9C	0.0692 (18)	0.0548 (14)	0.0431 (14)	0.0055 (13)	0.0174 (13)	0.0014 (11)
C10C	0.0652 (19)	0.0729 (18)	0.0543 (16)	0.0227 (15)	0.0221 (14)	0.0101 (14)
C11C	0.0523 (16)	0.0809 (18)	0.0639 (17)	0.0053 (16)	0.0097 (13)	0.0099 (15)
C12C	0.0572 (17)	0.0604 (15)	0.0634 (16)	−0.0056 (14)	0.0058 (13)	0.0032 (13)
ClD	0.2051 (10)	0.0741 (5)	0.1082 (7)	0.0049 (5)	−0.0065 (7)	0.0164 (5)
OD	0.0771 (12)	0.0584 (10)	0.0691 (12)	−0.0090 (8)	0.0298 (9)	−0.0139 (9)
C1D	0.0616 (18)	0.0692 (17)	0.0444 (15)	0.0056 (15)	0.0035 (13)	−0.0029 (12)
C2D	0.0704 (19)	0.083 (2)	0.0659 (18)	0.0005 (16)	0.0115 (14)	0.0042 (15)
C3D	0.102 (3)	0.087 (2)	0.071 (2)	−0.0230 (19)	0.0069 (17)	0.0121 (16)
C4D	0.119 (3)	0.0660 (18)	0.0576 (17)	0.002 (2)	−0.0048 (18)	0.0049 (14)
C5D	0.098 (3)	0.078 (2)	0.091 (2)	0.0205 (19)	−0.0011 (18)	0.0069 (17)
C6D	0.073 (2)	0.0752 (19)	0.079 (2)	0.0048 (16)	0.0056 (15)	0.0021 (15)
C7D	0.0504 (15)	0.0652 (16)	0.0497 (16)	0.0042 (12)	0.0031 (12)	−0.0118 (13)
C8D	0.0477 (14)	0.0552 (15)	0.0601 (17)	−0.0033 (12)	0.0107 (12)	−0.0172 (13)
C9D	0.0801 (18)	0.0553 (16)	0.0805 (19)	−0.0061 (14)	0.0156 (15)	−0.0088 (15)
C10D	0.101 (2)	0.0601 (17)	0.103 (3)	0.0088 (15)	0.007 (2)	−0.0225 (18)
C11D	0.116 (3)	0.083 (2)	0.077 (2)	0.0252 (18)	0.0096 (19)	−0.0338 (17)
C12D	0.092 (2)	0.093 (2)	0.0574 (17)	0.0155 (17)	0.0140 (15)	−0.0129 (16)

Geometric parameters (Å, º)

ClA—C4A	1.733 (2)	C9A—C10A	1.381 (3)
ClB—C4B	1.737 (2)	C9B—C10B	1.377 (3)
ClC—C4C	1.739 (2)	C9C—C10C	1.382 (3)
ClD—C4D	1.746 (3)	C9D—C10D	1.379 (3)
OA—C8A	1.387 (2)	C10A—C11A	1.368 (3)
OB—C8B	1.381 (2)	C10B—C11B	1.372 (3)
OC—C8C	1.378 (2)	C10C—C11C	1.374 (3)
OD—C8D	1.381 (2)	C10D—C11D	1.357 (4)
C1A—C2A	1.387 (3)	C11A—C12A	1.382 (3)
C1B—C2B	1.390 (3)	C11B—C12B	1.375 (3)
C1C—C2C	1.387 (3)	C11C—C12C	1.368 (3)
C1D—C2D	1.382 (3)	C11D—C12D	1.386 (3)
C1A—C6A	1.381 (3)	OA—HA	0.82
C1B—C6B	1.384 (3)	OB—HB	0.82
C1C—C6C	1.382 (3)	OC—HC	0.82
C1D—C6D	1.385 (3)	OD—HD	0.82
C1A—C7A	1.481 (3)	C2A—H2A	0.93
C1B—C7B	1.483 (3)	C2B—H2B	0.93
C1C—C7C	1.491 (3)	C2C—H2C	0.93
C1D—C7D	1.488 (3)	C2D—H2D	0.93
C2A—C3A	1.380 (3)	C3A—H3A	0.93
C2B—C3B	1.389 (3)	C3B—H3B	0.93
C2C—C3C	1.376 (3)	C3C—H3C	0.93
C2D—C3D	1.386 (3)	C3D—H3D	0.93
C3A—C4A	1.368 (3)	C5A—H5A	0.93
C3B—C4B	1.359 (3)	C5B—H5B	0.93
C3C—C4C	1.366 (3)	C5C—H5C	0.93
C3D—C4D	1.370 (4)	C5D—H5D	0.93
C4A—C5A	1.366 (3)	C6A—H6A	0.93
C4B—C5B	1.369 (3)	C6B—H6B	0.93
C4C—C5C	1.374 (3)	C6C—H6C	0.93
C4D—C5D	1.354 (4)	C6D—H6D	0.93
C5A—C6A	1.386 (3)	C9A—H9A	0.93
C5B—C6B	1.378 (3)	C9B—H9B	0.93
C5C—C6C	1.380 (3)	C9C—H9C	0.93
C5D—C6D	1.367 (3)	C9D—H9D	0.93
C7A—C8A	1.395 (3)	C10A—H10A	0.93
C7B—C8B	1.392 (3)	C10B—H10B	0.93
C7C—C8C	1.389 (3)	C10C—H10C	0.93
C7D—C8D	1.387 (3)	C10D—H10D	0.93
C7A—C12A	1.387 (3)	C11A—H11A	0.93
C7B—C12B	1.390 (3)	C11B—H11B	0.93
C7C—C12C	1.390 (3)	C11C—H11C	0.93
C7D—C12D	1.391 (3)	C11D—H11D	0.93
C8A—C9A	1.368 (3)	C12A—H12A	0.93
C8B—C9B	1.371 (3)	C12B—H12B	0.93
C8C—C9C	1.386 (3)	C12C—H12C	0.93
C8D—C9D	1.373 (3)	C12D—H12D	0.93
C2A—C1A—C6A	117.2 (2)	C10C—C11C—C12C	119.4 (2)
C2B—C1B—C6B	117.6 (2)	C10D—C11D—C12D	120.1 (2)
C2C—C1C—C6C	117.6 (2)	C7A—C12A—C11A	122.3 (2)
C2D—C1D—C6D	117.5 (2)	C7B—C12B—C11B	121.4 (2)
C2A—C1A—C7A	120.5 (2)	C7C—C12C—C11C	122.1 (2)
C2B—C1B—C7B	119.8 (2)	C7D—C12D—C11D	121.2 (3)
C2C—C1C—C7C	120.7 (2)	C8A—OA—HA	109.5
C2D—C1D—C7D	121.3 (2)	C8B—OB—HB	109.5
C6A—C1A—C7A	122.2 (2)	C8C—OC—HC	109.5
C6B—C1B—C7B	122.5 (2)	C8D—OD—HD	109.5
C6C—C1C—C7C	121.7 (2)	C1A—C2A—H2A	119.0
C6D—C1D—C7D	121.2 (2)	C1B—C2B—H2B	119.4
C1A—C2A—C3A	121.9 (2)	C1C—C2C—H2C	119.2
C1B—C2B—C3B	121.2 (2)	C1D—C2D—H2D	119.5
C1C—C2C—C3C	121.6 (2)	C3A—C2A—H2A	119.0
C1D—C2D—C3D	121.1 (2)	C3B—C2B—H2B	119.4
C2A—C3A—C4A	119.1 (2)	C3C—C2C—H2C	119.2
C2B—C3B—C4B	119.2 (2)	C3D—C2D—H2D	119.5
C2C—C3C—C4C	119.5 (2)	C2A—C3A—H3A	120.4
C2D—C3D—C4D	119.0 (3)	C2B—C3B—H3B	120.4
C3A—C4A—C5A	120.6 (2)	C2C—C3C—H3C	120.3
C3B—C4B—C5B	121.1 (2)	C2D—C3D—H3D	120.5
C3C—C4C—C5C	120.6 (2)	C4A—C3A—H3A	120.4
C3D—C4D—C5D	121.2 (3)	C4B—C3B—H3B	120.4
C3A—C4A—ClA	119.4 (2)	C4C—C3C—H3C	120.3
C3B—C4B—ClB	118.5 (3)	C4D—C3D—H3D	120.5
C3C—C4C—ClC	119.9 (2)	C4A—C5A—H5A	120.1
C3D—C4D—ClD	119.0 (3)	C4B—C5B—H5B	120.2
C5A—C4A—ClA	119.9 (2)	C4C—C5C—H5C	120.3
C5B—C4B—ClB	120.3 (2)	C4D—C5D—H5D	120.2
C5C—C4C—ClC	119.5 (2)	C6A—C5A—H5A	120.1
C5D—C4D—ClD	119.8 (3)	C6B—C5B—H5B	120.2
C4A—C5A—C6A	119.7 (2)	C6C—C5C—H5C	120.3
C4B—C5B—C6B	119.6 (2)	C6D—C5D—H5D	120.2
C4C—C5C—C6C	119.5 (2)	C1A—C6A—H6A	119.3
C4D—C5D—C6D	119.5 (3)	C1B—C6B—H6B	119.4
C1A—C6A—C5A	121.3 (2)	C1C—C6C—H6C	119.4
C1B—C6B—C5B	121.2 (2)	C1D—C6D—H6D	119.1
C1C—C6C—C5C	121.3 (2)	C5A—C6A—H6A	119.3
C1D—C6D—C5D	121.7 (3)	C5B—C6B—H6B	119.4
C1A—C7A—C8A	123.0 (2)	C5C—C6C—H6C	119.4
C1B—C7B—C8B	121.6 (2)	C5D—C6D—H6D	119.1
C1C—C7C—C8C	122.3 (2)	C10A—C9A—H9A	119.8
C1D—C7D—C8D	121.8 (2)	C10B—C9B—H9B	120.0
C1A—C7A—C12A	120.1 (2)	C10C—C9C—H9C	120.0
C1B—C7B—C12B	121.1 (2)	C10D—C9D—H9D	120.5
C1C—C7C—C12C	119.7 (2)	C8A—C9A—H9A	119.8
C1D—C7D—C12D	121.4 (2)	C8B—C9B—H9B	120.0
C8A—C7A—C12A	116.8 (2)	C8C—C9C—H9C	120.0
C8B—C7B—C12B	117.3 (2)	C8D—C9D—H9D	120.5
C8C—C7C—C12C	117.9 (2)	C9A—C10A—H10A	120.0
C8D—C7D—C12D	116.7 (2)	C9B—C10B—H10B	120.1
C7A—C8A—C9A	121.3 (2)	C9C—C10C—H10C	119.9
C7B—C8B—C9B	121.5 (2)	C9D—C10D—H10D	119.8
C7C—C8C—C9C	120.4 (2)	C11A—C10A—H10A	120.0
C7D—C8D—C9D	122.5 (2)	C11B—C10B—H10B	120.1
OA—C8A—C7A	117.3 (2)	C11C—C10C—H10C	119.9
OB—C8B—C7B	117.39 (19)	C11D—C10D—H10D	119.8
OC—C8C—C7C	117.86 (19)	C10A—C11A—H11A	120.4
OD—C8D—C7D	116.9 (2)	C10B—C11B—H11B	120.0
OA—C8A—C9A	121.3 (2)	C10C—C11C—H11C	120.3
OB—C8B—C9B	121.1 (2)	C10D—C11D—H11D	119.9
OC—C8C—C9C	121.7 (2)	C12A—C11A—H11A	120.4
OD—C8D—C9D	120.6 (2)	C12B—C11B—H11B	120.0
C8A—C9A—C10A	120.3 (2)	C12C—C11C—H11C	120.3
C8B—C9B—C10B	120.0 (2)	C12D—C11D—H11D	119.9
C8C—C9C—C10C	120.0 (2)	C7A—C12A—H12A	118.8
C8D—C9D—C10D	119.0 (2)	C7B—C12B—H12B	119.3
C9A—C10A—C11A	120.0 (2)	C7C—C12C—H12C	119.0
C9B—C10B—C11B	119.8 (2)	C7D—C12D—H12D	119.4
C9C—C10C—C11C	120.2 (2)	C11A—C12A—H12A	118.8
C9D—C10D—C11D	120.4 (2)	C11B—C12B—H12B	119.3
C10A—C11A—C12A	119.2 (2)	C11C—C12C—H12C	119.0
C10B—C11B—C12B	120.1 (2)	C11D—C12D—H12D	119.4
C6A—C1A—C2A—C3A	−0.7 (3)	ClC—C4C—C5C—C6C	178.16 (16)
C6B—C1B—C2B—C3B	3.0 (3)	ClD—C4D—C5D—C6D	178.93 (19)
C6C—C1C—C2C—C3C	0.1 (3)	C4A—C5A—C6A—C1A	−0.7 (4)
C6D—C1D—C2D—C3D	−0.2 (3)	C4B—C5B—C6B—C1B	−0.1 (3)
C7A—C1A—C2A—C3A	176.5 (2)	C4C—C5C—C6C—C1C	1.4 (3)
C7B—C1B—C2B—C3B	−177.8 (2)	C4D—C5D—C6D—C1D	0.1 (4)
C7C—C1C—C2C—C3C	−178.0 (2)	C1A—C7A—C8A—C9A	178.7 (2)
C7D—C1D—C2D—C3D	178.8 (2)	C1B—C7B—C8B—C9B	−178.8 (2)
C2A—C1A—C6A—C5A	1.4 (3)	C1C—C7C—C8C—C9C	−178.72 (18)
C2B—C1B—C6B—C5B	−2.3 (3)	C1D—C7D—C8D—C9D	−179.9 (2)
C2C—C1C—C6C—C5C	−0.8 (3)	C1A—C7A—C8A—OA	−4.0 (3)
C2D—C1D—C6D—C5D	−0.1 (3)	C1B—C7B—C8B—OB	−1.4 (3)
C7A—C1A—C6A—C5A	−175.8 (2)	C1C—C7C—C8C—OC	3.5 (3)
C7B—C1B—C6B—C5B	178.60 (19)	C1D—C7D—C8D—OD	2.1 (3)
C7C—C1C—C6C—C5C	177.19 (19)	C12A—C7A—C8A—C9A	−1.4 (3)
C7D—C1D—C6D—C5D	−179.1 (2)	C12B—C7B—C8B—C9B	−0.3 (3)
C2A—C1A—C7A—C8A	132.7 (2)	C12C—C7C—C8C—C9C	1.4 (3)
C2B—C1B—C7B—C8B	128.4 (2)	C12D—C7D—C8D—C9D	0.1 (3)
C2C—C1C—C7C—C8C	−130.3 (2)	C12A—C7A—C8A—OA	175.87 (18)
C2D—C1D—C7D—C8D	−119.8 (2)	C12B—C7B—C8B—OB	177.12 (19)
C2A—C1A—C7A—C12A	−47.2 (3)	C12C—C7C—C8C—OC	−176.45 (17)
C2B—C1B—C7B—C12B	−50.0 (3)	C12D—C7D—C8D—OD	−177.87 (19)
C2C—C1C—C7C—C12C	49.6 (3)	C1A—C7A—C12A—C11A	−179.4 (2)
C2D—C1D—C7D—C12D	60.1 (3)	C1B—C7B—C12B—C11B	179.5 (2)
C6A—C1A—C7A—C8A	−50.2 (3)	C1C—C7C—C12C—C11C	179.7 (2)
C6B—C1B—C7B—C8B	−52.5 (3)	C1D—C7D—C12D—C11D	179.4 (2)
C6C—C1C—C7C—C8C	51.8 (3)	C8A—C7A—C12A—C11A	0.7 (3)
C6D—C1D—C7D—C8D	59.1 (3)	C8B—C7B—C12B—C11B	1.0 (4)
C6A—C1A—C7A—C12A	129.9 (2)	C8C—C7C—C12C—C11C	−0.4 (3)
C6B—C1B—C7B—C12B	129.1 (2)	C8D—C7D—C12D—C11D	−0.7 (4)
C6C—C1C—C7C—C12C	−128.3 (2)	C7A—C8A—C9A—C10A	0.7 (3)
C6D—C1D—C7D—C12D	−120.9 (3)	C7B—C8B—C9B—C10B	−0.8 (3)
C1A—C2A—C3A—C4A	−0.6 (4)	C7C—C8C—C9C—C10C	−1.1 (3)
C1B—C2B—C3B—C4B	−1.3 (4)	C7D—C8D—C9D—C10D	0.3 (4)
C1C—C2C—C3C—C4C	0.1 (4)	OA—C8A—C9A—C10A	−176.5 (2)
C1D—C2D—C3D—C4D	0.5 (4)	OB—C8B—C9B—C10B	−178.1 (2)
C2A—C3A—C4A—C5A	1.3 (4)	OC—C8C—C9C—C10C	176.63 (19)
C2B—C3B—C4B—C5B	−1.3 (4)	OD—C8D—C9D—C10D	178.2 (2)
C2C—C3C—C4C—C5C	0.6 (4)	C8A—C9A—C10A—C11A	0.8 (4)
C2D—C3D—C4D—C5D	−0.6 (4)	C8B—C9B—C10B—C11B	1.2 (4)
C2A—C3A—C4A—ClA	−178.89 (18)	C8C—C9C—C10C—C11C	−0.2 (3)
C2B—C3B—C4B—ClB	178.16 (18)	C8D—C9D—C10D—C11D	−0.2 (4)
C2C—C3C—C4C—ClC	−178.90 (19)	C9A—C10A—C11A—C12A	−1.5 (4)
C2D—C3D—C4D—ClD	−179.24 (19)	C9B—C10B—C11B—C12B	−0.5 (4)
C3A—C4A—C5A—C6A	−0.7 (4)	C9C—C10C—C11C—C12C	1.1 (3)
C3B—C4B—C5B—C6B	2.0 (4)	C9D—C10D—C11D—C12D	−0.3 (4)
C3C—C4C—C5C—C6C	−1.3 (3)	C10A—C11A—C12A—C7A	0.8 (4)
C3D—C4D—C5D—C6D	0.3 (4)	C10B—C11B—C12B—C7B	−0.6 (4)
ClA—C4A—C5A—C6A	179.53 (17)	C10C—C11C—C12C—C7C	−0.8 (3)
ClB—C4B—C5B—C6B	−177.44 (16)	C10D—C11D—C12D—C7D	0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OA—HA···OB	0.82	2.15	2.943 (2)	164 (4)
OB—HB···OC	0.82	2.14	2.892 (2)	153 (4)
OC—HC···OD	0.82	1.98	2.797 (2)	172 (4)
OD—HD···OA	0.82	2.07	2.781 (2)	144 (4)

(k00201) 4-chloro-2'-biphenylol

Crystal data

C12H9ClO	Dx = 1.353 Mg m^−3
Mr = 204.64	Melting point: 41-43_C K
Monoclinic, P121/c1	Mo Kα radiation, λ = 0.71073 Å
a = 17.211 (3) Å	Cell parameters from 20387 reflections
b = 11.962 (2) Å	θ = 1.0–25.0°
c = 19.621 (3) Å	µ = 0.34 mm^−1
β = 95.95 (2)°	T = 142 K
V = 4017.8 (11) Å^3	Pointed laths elongated along b. Crystals are thinnest in direction a*., colourless
Z = 16	0.41 × 0.25 × 0.05 mm
F(000) = 1696

Data collection

Nonius Kappa-CCD diffractometer	7080 independent reflections
Radiation source: fine-focus sealed tube	4349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 1.2°
ω scans with 2.0° steps at χ=55°	h = −20→20
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	k = −14→11
Tmin = 0.87, Tmax = 0.98	l = −23→23
11717 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
7080 reflections	Δρmax = 0.33 e Å^−3
522 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00049 (9)

Special details

Experimental. The crystal-to-detector distance was 45 mm. Each frame was measured for 40 s. The number of scan sets measured was 4; the total number of frames measured was 256.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
ClA	0.85485 (4)	0.67701 (6)	0.65086 (3)	0.0506 (2)
OA	0.82192 (9)	0.14121 (15)	0.56739 (8)	0.0298 (5)
HA	0.8098 (13)	0.0886 (18)	0.5419 (11)	0.043 (9)*
C1A	0.88220 (12)	0.3009 (2)	0.66576 (11)	0.0263 (6)
C2A	0.85684 (12)	0.3636 (2)	0.71924 (12)	0.0312 (6)
H2A	0.8454	0.3262	0.7597	0.037*
C3A	0.84789 (12)	0.4786 (2)	0.71514 (12)	0.0333 (6)
H3A	0.8307	0.5196	0.7522	0.040*
C4A	0.86444 (12)	0.5320 (2)	0.65635 (13)	0.0317 (6)
C5A	0.88895 (12)	0.4734 (2)	0.60218 (12)	0.0334 (7)
H5A	0.9000	0.5116	0.5619	0.040*
C6A	0.89746 (12)	0.3586 (2)	0.60664 (11)	0.0330 (7)
H6A	0.9139	0.3183	0.5690	0.040*
C7A	0.89580 (12)	0.1793 (2)	0.67404 (11)	0.0261 (6)
C8A	0.86839 (12)	0.1007 (2)	0.62469 (11)	0.0252 (6)
C9A	0.88308 (12)	−0.0115 (2)	0.63300 (12)	0.0318 (6)
H9A	0.8639	−0.0629	0.5984	0.038*
C10A	0.92588 (13)	−0.0493 (2)	0.69203 (12)	0.0332 (6)
H10A	0.9371	−0.1268	0.6976	0.040*
C11A	0.95252 (12)	0.0258 (2)	0.74321 (12)	0.0326 (6)
H11A	0.9807	0.0001	0.7844	0.039*
C12A	0.93760 (12)	0.1379 (2)	0.73340 (11)	0.0303 (6)
H12A	0.9564	0.1890	0.7683	0.036*
ClB	0.91269 (4)	0.40903 (5)	0.41272 (3)	0.0552 (2)
OB	0.75170 (9)	−0.04981 (13)	0.49380 (8)	0.0280 (4)
HB	0.7189 (11)	−0.0815 (17)	0.5131 (10)	0.027 (8)*
C1B	0.86689 (13)	0.03693 (19)	0.41734 (10)	0.0252 (6)
C2B	0.94130 (13)	0.0806 (2)	0.43262 (11)	0.0340 (7)
H2B	0.9835	0.0308	0.4447	0.041*
C3B	0.95622 (14)	0.1939 (2)	0.43090 (11)	0.0380 (7)
H3B	1.0077	0.2218	0.4421	0.046*
C4B	0.89518 (16)	0.2658 (2)	0.41260 (11)	0.0353 (7)
C5B	0.82057 (14)	0.2258 (2)	0.39382 (11)	0.0322 (6)
H5B	0.7793	0.2758	0.3791	0.039*
C6B	0.80673 (13)	0.1121 (2)	0.39670 (10)	0.0272 (6)
H6B	0.7554	0.0845	0.3844	0.033*
C7B	0.85300 (12)	−0.08488 (19)	0.42319 (11)	0.0249 (6)
C8B	0.79486 (12)	−0.1267 (2)	0.46116 (11)	0.0239 (6)
C9B	0.78249 (13)	−0.2404 (2)	0.46716 (11)	0.0310 (6)
H9B	0.7422	−0.2670	0.4926	0.037*
C10B	0.82888 (14)	−0.3150 (2)	0.43607 (12)	0.0379 (7)
H10B	0.8206	−0.3931	0.4401	0.045*
C11B	0.88765 (14)	−0.2758 (2)	0.39894 (12)	0.0406 (7)
H11B	0.9198	−0.3271	0.3778	0.049*
C12B	0.89921 (13)	−0.1628 (2)	0.39282 (12)	0.0345 (7)
H12B	0.9396	−0.1369	0.3673	0.041*
ClC	0.71975 (3)	−0.60592 (5)	0.49132 (3)	0.0413 (2)
OC	0.64090 (9)	−0.09731 (15)	0.58858 (8)	0.0276 (4)
HC	0.6545 (13)	−0.0408 (17)	0.6065 (11)	0.033 (9)*
C1C	0.57711 (12)	−0.30037 (19)	0.53329 (11)	0.0233 (6)
C2C	0.56888 (13)	−0.35242 (19)	0.46974 (12)	0.0334 (7)
H2C	0.5329	−0.3226	0.4344	0.040*
C3C	0.61162 (14)	−0.4466 (2)	0.45648 (12)	0.0369 (7)
H3C	0.6052	−0.4812	0.4127	0.044*
C4C	0.66364 (12)	−0.48920 (18)	0.50806 (12)	0.0293 (6)
C5C	0.67342 (12)	−0.44015 (19)	0.57197 (11)	0.0275 (6)
H5C	0.7092	−0.4707	0.6072	0.033*
C6C	0.63046 (12)	−0.34599 (18)	0.58404 (11)	0.0251 (6)
H6C	0.6374	−0.3116	0.6279	0.030*
C7C	0.52898 (13)	−0.20204 (19)	0.54693 (10)	0.0229 (6)
C8C	0.56037 (13)	−0.1033 (2)	0.57603 (10)	0.0222 (6)
C9C	0.51281 (13)	−0.01386 (19)	0.58912 (10)	0.0256 (6)
H9C	0.5351	0.0523	0.6096	0.031*
C10C	0.43317 (13)	−0.0209 (2)	0.57245 (10)	0.0284 (6)
H10C	0.4007	0.0404	0.5814	0.034*
C11C	0.40040 (13)	−0.1174 (2)	0.54274 (11)	0.0299 (6)
H11C	0.3456	−0.1223	0.5309	0.036*
C12C	0.44825 (13)	−0.20594 (19)	0.53058 (10)	0.0276 (6)
H12C	0.4254	−0.2719	0.5104	0.033*
ClD	0.67308 (4)	−0.35580 (5)	0.79278 (3)	0.0580 (2)
OD	0.69079 (9)	0.11209 (13)	0.63502 (8)	0.0318 (5)
HD	0.7205 (14)	0.143 (2)	0.6094 (13)	0.074 (11)*
C1D	0.65087 (13)	0.0162 (2)	0.75648 (10)	0.0267 (6)
C2D	0.58603 (14)	−0.0478 (2)	0.76689 (11)	0.0336 (6)
H2D	0.5364	−0.0130	0.7662	0.040*
C3D	0.59268 (15)	−0.1623 (2)	0.77826 (11)	0.0373 (7)
H3D	0.5479	−0.2058	0.7850	0.045*
C4D	0.66480 (17)	−0.2115 (2)	0.77959 (11)	0.0372 (7)
C5D	0.73011 (15)	−0.1504 (2)	0.76963 (11)	0.0402 (7)
H5D	0.7796	−0.1857	0.7706	0.048*
C6D	0.72290 (14)	−0.0369 (2)	0.75820 (11)	0.0347 (7)
H6D	0.7680	0.0057	0.7514	0.042*
C7D	0.64328 (12)	0.1384 (2)	0.74268 (12)	0.0260 (6)
C8D	0.66476 (12)	0.1853 (2)	0.68252 (12)	0.0254 (6)
C9D	0.65814 (12)	0.2975 (2)	0.66855 (12)	0.0319 (6)
H9D	0.6729	0.3264	0.6267	0.038*
C10D	0.62981 (13)	0.3681 (2)	0.71600 (13)	0.0387 (7)
H10D	0.6253	0.4460	0.7070	0.046*
C11D	0.60807 (14)	0.3253 (2)	0.77646 (13)	0.0424 (7)
H11D	0.5889	0.3737	0.8092	0.051*
C12D	0.61423 (13)	0.2116 (2)	0.78936 (12)	0.0396 (7)
H12D	0.5983	0.1828	0.8309	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
ClA	0.0562 (5)	0.0354 (4)	0.0576 (5)	−0.0049 (4)	−0.0064 (4)	0.0021 (4)
OA	0.0311 (11)	0.0363 (12)	0.0214 (10)	−0.0011 (9)	0.0002 (8)	−0.0075 (10)
C1A	0.0203 (14)	0.0372 (17)	0.0209 (15)	−0.0027 (12)	−0.0004 (11)	−0.0048 (14)
C2A	0.0307 (15)	0.0381 (17)	0.0251 (15)	−0.0053 (13)	0.0045 (12)	0.0000 (14)
C3A	0.0305 (16)	0.0399 (18)	0.0294 (16)	−0.0027 (13)	0.0023 (12)	−0.0059 (15)
C4A	0.0247 (15)	0.0316 (16)	0.0369 (17)	−0.0082 (12)	−0.0062 (13)	0.0009 (14)
C5A	0.0281 (15)	0.0459 (19)	0.0253 (16)	−0.0088 (14)	−0.0013 (12)	0.0059 (15)
C6A	0.0293 (15)	0.0457 (19)	0.0241 (16)	−0.0049 (13)	0.0035 (12)	−0.0049 (14)
C7A	0.0198 (14)	0.0374 (17)	0.0219 (15)	−0.0016 (12)	0.0060 (12)	−0.0035 (14)
C8A	0.0175 (14)	0.0373 (17)	0.0208 (15)	0.0030 (13)	0.0017 (11)	−0.0011 (14)
C9A	0.0256 (15)	0.0390 (18)	0.0301 (16)	0.0029 (13)	−0.0006 (12)	−0.0081 (14)
C10A	0.0276 (15)	0.0319 (17)	0.0398 (17)	0.0072 (13)	0.0025 (13)	−0.0028 (14)
C11A	0.0254 (15)	0.0417 (18)	0.0298 (16)	0.0024 (13)	−0.0017 (12)	−0.0018 (15)
C12A	0.0257 (15)	0.0398 (18)	0.0251 (15)	−0.0014 (13)	0.0009 (12)	−0.0043 (14)
ClB	0.0831 (6)	0.0322 (4)	0.0563 (5)	−0.0090 (4)	0.0354 (4)	−0.0019 (4)
OB	0.0245 (10)	0.0314 (11)	0.0298 (10)	−0.0023 (9)	0.0111 (8)	−0.0008 (9)
C1B	0.0245 (15)	0.0313 (16)	0.0212 (14)	0.0023 (13)	0.0093 (11)	0.0004 (12)
C2B	0.0276 (16)	0.0394 (18)	0.0362 (16)	0.0040 (13)	0.0095 (12)	0.0030 (14)
C3B	0.0324 (16)	0.0402 (19)	0.0441 (17)	−0.0101 (15)	0.0166 (13)	−0.0041 (15)
C4B	0.0508 (18)	0.0293 (17)	0.0296 (16)	−0.0032 (15)	0.0220 (14)	−0.0019 (13)
C5B	0.0448 (18)	0.0291 (17)	0.0245 (15)	0.0088 (14)	0.0119 (13)	0.0028 (13)
C6B	0.0268 (15)	0.0351 (17)	0.0210 (14)	0.0049 (13)	0.0080 (11)	−0.0004 (13)
C7B	0.0204 (14)	0.0307 (16)	0.0231 (14)	0.0022 (12)	−0.0005 (11)	−0.0003 (13)
C8B	0.0239 (14)	0.0285 (16)	0.0188 (14)	0.0050 (13)	0.0005 (11)	−0.0037 (13)
C9B	0.0302 (15)	0.0329 (17)	0.0297 (15)	−0.0025 (14)	0.0030 (12)	−0.0010 (14)
C10B	0.0450 (17)	0.0268 (16)	0.0415 (17)	0.0015 (14)	0.0033 (14)	−0.0005 (14)
C11B	0.0441 (17)	0.0340 (18)	0.0453 (17)	0.0133 (15)	0.0121 (14)	−0.0060 (15)
C12B	0.0289 (15)	0.0395 (18)	0.0370 (16)	0.0082 (14)	0.0120 (12)	−0.0032 (15)
ClC	0.0340 (4)	0.0328 (4)	0.0580 (5)	0.0024 (3)	0.0091 (3)	−0.0121 (4)
OC	0.0250 (11)	0.0272 (11)	0.0302 (11)	−0.0028 (9)	0.0010 (8)	−0.0069 (9)
C1C	0.0209 (14)	0.0242 (15)	0.0247 (15)	−0.0041 (12)	0.0028 (11)	0.0020 (13)
C2C	0.0392 (16)	0.0337 (17)	0.0252 (16)	0.0072 (13)	−0.0069 (12)	−0.0031 (14)
C3C	0.0455 (17)	0.0345 (17)	0.0298 (16)	−0.0013 (14)	0.0002 (14)	−0.0116 (14)
C4C	0.0251 (15)	0.0242 (15)	0.0389 (16)	−0.0007 (12)	0.0050 (13)	−0.0034 (14)
C5C	0.0237 (14)	0.0259 (15)	0.0325 (16)	−0.0025 (12)	0.0006 (12)	0.0022 (13)
C6C	0.0271 (15)	0.0251 (15)	0.0230 (14)	−0.0042 (12)	0.0014 (12)	−0.0047 (12)
C7C	0.0224 (14)	0.0300 (16)	0.0166 (13)	−0.0005 (13)	0.0032 (11)	0.0035 (12)
C8C	0.0186 (14)	0.0337 (16)	0.0150 (13)	−0.0004 (13)	0.0047 (11)	0.0028 (12)
C9C	0.0345 (16)	0.0264 (15)	0.0168 (13)	0.0017 (13)	0.0065 (12)	−0.0023 (12)
C10C	0.0281 (16)	0.0365 (17)	0.0218 (14)	0.0079 (13)	0.0084 (12)	0.0063 (13)
C11C	0.0209 (14)	0.0411 (17)	0.0279 (15)	−0.0015 (14)	0.0035 (11)	0.0068 (14)
C12C	0.0285 (15)	0.0298 (16)	0.0246 (14)	−0.0037 (13)	0.0037 (12)	0.0005 (12)
ClD	0.0859 (6)	0.0366 (5)	0.0490 (5)	0.0036 (4)	−0.0058 (4)	0.0066 (4)
OD	0.0362 (11)	0.0300 (11)	0.0319 (11)	−0.0031 (9)	0.0156 (9)	−0.0057 (9)
C1D	0.0246 (15)	0.0364 (17)	0.0185 (14)	0.0036 (13)	−0.0006 (11)	−0.0031 (13)
C2D	0.0316 (16)	0.0428 (18)	0.0271 (15)	0.0040 (14)	0.0066 (12)	0.0012 (14)
C3D	0.0406 (18)	0.0421 (19)	0.0291 (16)	−0.0061 (15)	0.0024 (13)	0.0049 (14)
C4D	0.0564 (19)	0.0316 (17)	0.0223 (15)	0.0021 (16)	−0.0021 (14)	0.0013 (13)
C5D	0.0413 (18)	0.0438 (19)	0.0345 (17)	0.0120 (15)	−0.0015 (13)	0.0012 (15)
C6D	0.0336 (17)	0.0379 (18)	0.0322 (16)	−0.0007 (14)	0.0022 (12)	0.0003 (14)
C7D	0.0203 (14)	0.0328 (16)	0.0243 (15)	0.0020 (12)	−0.0004 (11)	−0.0050 (14)
C8D	0.0167 (13)	0.0313 (17)	0.0281 (15)	−0.0007 (12)	0.0022 (11)	−0.0109 (14)
C9D	0.0341 (15)	0.0285 (17)	0.0335 (16)	−0.0044 (13)	0.0064 (12)	−0.0047 (14)
C10D	0.0429 (17)	0.0273 (16)	0.0446 (18)	0.0021 (13)	−0.0017 (14)	−0.0111 (15)
C11D	0.0489 (18)	0.044 (2)	0.0330 (18)	0.0133 (15)	−0.0002 (14)	−0.0157 (16)
C12D	0.0413 (17)	0.052 (2)	0.0257 (15)	0.0079 (15)	0.0025 (13)	−0.0043 (16)

Geometric parameters (Å, º)

ClA—C4A	1.744 (2)	C8A—C9A	1.372 (3)
ClB—C4B	1.739 (2)	C8B—C9B	1.383 (3)
ClC—C4C	1.748 (2)	C8C—C9C	1.388 (3)
ClD—C4D	1.749 (2)	C8D—C9D	1.372 (3)
OA—C8A	1.397 (2)	C9A—C10A	1.383 (3)
OB—C8B	1.381 (2)	C9B—C10B	1.381 (3)
OC—C8C	1.384 (2)	C9C—C10C	1.378 (3)
OD—C8D	1.386 (2)	C9D—C10D	1.383 (3)
OA—HA	0.82 (2)	C10A—C11A	1.390 (3)
OB—HB	0.81 (2)	C10B—C11B	1.388 (3)
OC—HC	0.79 (2)	C10C—C11C	1.386 (3)
OD—HD	0.84 (2)	C10D—C11D	1.379 (3)
C1A—C2A	1.396 (3)	C11A—C12A	1.374 (3)
C1B—C2B	1.387 (3)	C11B—C12B	1.374 (3)
C1C—C2C	1.388 (3)	C11C—C12C	1.378 (3)
C1D—C2D	1.386 (3)	C11D—C12D	1.385 (3)
C1A—C6A	1.398 (3)	C2A—H2A	0.95
C1B—C6B	1.399 (3)	C2B—H2B	0.95
C1C—C6C	1.394 (3)	C2C—H2C	0.95
C1D—C6D	1.390 (3)	C2D—H2D	0.95
C1A—C7A	1.480 (3)	C3A—H3A	0.95
C1B—C7B	1.483 (3)	C3B—H3B	0.95
C1C—C7C	1.479 (3)	C3C—H3C	0.95
C1D—C7D	1.490 (3)	C3D—H3D	0.95
C2A—C3A	1.386 (3)	C5A—H5A	0.95
C2B—C3B	1.381 (3)	C5B—H5B	0.95
C2C—C3C	1.385 (3)	C5C—H5C	0.95
C2D—C3D	1.390 (3)	C5D—H5D	0.95
C3A—C4A	1.374 (3)	C6A—H6A	0.95
C3B—C4B	1.376 (3)	C6B—H6B	0.95
C3C—C4C	1.378 (3)	C6C—H6C	0.95
C3D—C4D	1.371 (3)	C6D—H6D	0.95
C4A—C5A	1.376 (3)	C9A—H9A	0.95
C4B—C5B	1.384 (3)	C9B—H9B	0.95
C4C—C5C	1.379 (3)	C9C—H9C	0.95
C4D—C5D	1.372 (3)	C9D—H9D	0.95
C5A—C6A	1.383 (3)	C10A—H10A	0.95
C5B—C6B	1.383 (3)	C10B—H10B	0.95
C5C—C6C	1.381 (3)	C10C—H10C	0.95
C5D—C6D	1.379 (3)	C10D—H10D	0.95
C7A—C8A	1.396 (3)	C11A—H11A	0.95
C7B—C8B	1.401 (3)	C11B—H11B	0.95
C7C—C8C	1.396 (3)	C11C—H11C	0.95
C7D—C8D	1.391 (3)	C11D—H11D	0.95
C7A—C12A	1.395 (3)	C12A—H12A	0.95
C7B—C12B	1.398 (3)	C12B—H12B	0.95
C7C—C12C	1.394 (3)	C12C—H12C	0.95
C7D—C12D	1.397 (3)	C12D—H12D	0.95
C8A—OA—HA	108 (2)	C9C—C10C—C11C	120.2 (2)
C8B—OB—HB	110 (2)	C9D—C10D—C11D	119.9 (2)
C8C—OC—HC	112 (2)	C10A—C11A—C12A	119.1 (2)
C8D—OD—HD	112 (2)	C10B—C11B—C12B	119.8 (2)
C2A—C1A—C6A	117.3 (2)	C10C—C11C—C12C	119.2 (2)
C2B—C1B—C6B	117.4 (2)	C10D—C11D—C12D	120.0 (2)
C2C—C1C—C6C	117.7 (2)	C7A—C12A—C11A	122.4 (2)
C2D—C1D—C6D	118.3 (2)	C7B—C12B—C11B	121.7 (2)
C2A—C1A—C7A	120.2 (2)	C7C—C12C—C11C	122.3 (2)
C2B—C1B—C7B	120.4 (2)	C7D—C12D—C11D	121.4 (2)
C2C—C1C—C7C	120.8 (2)	C1A—C2A—H2A	119.0
C2D—C1D—C7D	120.8 (2)	C1B—C2B—H2B	118.8
C6A—C1A—C7A	122.3 (2)	C1C—C2C—H2C	119.1
C6B—C1B—C7B	122.2 (2)	C1D—C2D—H2D	119.5
C6C—C1C—C7C	121.5 (2)	C3A—C2A—H2A	119.0
C6D—C1D—C7D	120.9 (2)	C3B—C2B—H2B	118.8
C1A—C2A—C3A	122.1 (2)	C3C—C2C—H2C	119.1
C1B—C2B—C3B	122.3 (2)	C3D—C2D—H2D	119.5
C1C—C2C—C3C	121.8 (2)	C2A—C3A—H3A	120.7
C1D—C2D—C3D	120.9 (2)	C2B—C3B—H3B	120.6
C2A—C3A—C4A	118.6 (2)	C2C—C3C—H3C	120.6
C2B—C3B—C4B	118.7 (2)	C2D—C3D—H3D	120.5
C2C—C3C—C4C	118.7 (2)	C4A—C3A—H3A	120.7
C2D—C3D—C4D	119.0 (2)	C4B—C3B—H3B	120.6
C3A—C4A—C5A	121.2 (2)	C4C—C3C—H3C	120.6
C3B—C4B—C5B	121.0 (2)	C4D—C3D—H3D	120.5
C3C—C4C—C5C	121.3 (2)	C4A—C5A—H5A	120.1
C3D—C4D—C5D	121.5 (2)	C4B—C5B—H5B	120.4
C3A—C4A—ClA	119.2 (2)	C4C—C5C—H5C	120.5
C3B—C4B—ClB	119.2 (2)	C4D—C5D—H5D	120.4
C3C—C4C—ClC	119.1 (2)	C6A—C5A—H5A	120.1
C3D—C4D—ClD	119.1 (2)	C6B—C5B—H5B	120.4
C5A—C4A—ClA	119.6 (2)	C6C—C5C—H5C	120.5
C5B—C4B—ClB	119.8 (2)	C6D—C5D—H5D	120.4
C5C—C4C—ClC	119.5 (2)	C1A—C6A—H6A	119.5
C5D—C4D—ClD	119.4 (2)	C1B—C6B—H6B	119.4
C4A—C5A—C6A	119.8 (2)	C1C—C6C—H6C	119.3
C4B—C5B—C6B	119.2 (2)	C1D—C6D—H6D	119.4
C4C—C5C—C6C	119.1 (2)	C5A—C6A—H6A	119.5
C4D—C5D—C6D	119.1 (2)	C5B—C6B—H6B	119.4
C1A—C6A—C5A	121.0 (2)	C5C—C6C—H6C	119.3
C1B—C6B—C5B	121.2 (2)	C5D—C6D—H6D	119.4
C1C—C6C—C5C	121.4 (2)	C8A—C9A—H9A	120.2
C1D—C6D—C5D	121.2 (2)	C8B—C9B—H9B	120.1
C1A—C7A—C8A	123.2 (2)	C8C—C9C—H9C	120.0
C1B—C7B—C8B	121.5 (2)	C8D—C9D—H9D	120.3
C1C—C7C—C8C	123.1 (2)	C10A—C9A—H9A	120.2
C1D—C7D—C8D	121.6 (2)	C10B—C9B—H9B	120.1
C1A—C7A—C12A	120.2 (2)	C10C—C9C—H9C	120.0
C1B—C7B—C12B	121.2 (2)	C10D—C9D—H9D	120.3
C1C—C7C—C12C	119.7 (2)	C9A—C10A—H10A	120.0
C1D—C7D—C12D	121.8 (2)	C9B—C10B—H10B	120.0
C8A—C7A—C12A	116.6 (2)	C9C—C10C—H10C	119.9
C8B—C7B—C12B	117.3 (2)	C9D—C10D—H10D	120.1
C8C—C7C—C12C	117.2 (2)	C11A—C10A—H10A	120.0
C8D—C7D—C12D	116.7 (2)	C11B—C10B—H10B	120.0
C7A—C8A—C9A	122.1 (2)	C11C—C10C—H10C	119.9
C7B—C8B—C9B	121.4 (2)	C11D—C10D—H10D	120.1
C7C—C8C—C9C	121.2 (2)	C10A—C11A—H11A	120.4
C7D—C8D—C9D	122.7 (2)	C10B—C11B—H11B	120.1
OA—C8A—C7A	116.6 (2)	C10C—C11C—H11C	120.4
OB—C8B—C7B	117.2 (2)	C10D—C11D—H11D	120.0
OC—C8C—C7C	117.1 (2)	C12A—C11A—H11A	120.4
OD—C8D—C7D	116.7 (2)	C12B—C11B—H11B	120.1
OA—C8A—C9A	121.2 (2)	C12C—C11C—H11C	120.4
OB—C8B—C9B	121.4 (2)	C12D—C11D—H11D	120.0
OC—C8C—C9C	121.7 (2)	C7A—C12A—H12A	118.8
OD—C8D—C9D	120.6 (2)	C7B—C12B—H12B	119.2
C8A—C9A—C10A	119.7 (2)	C7C—C12C—H12C	118.9
C8B—C9B—C10B	119.8 (2)	C7D—C12D—H12D	119.3
C8C—C9C—C10C	120.0 (2)	C11A—C12A—H12A	118.8
C8D—C9D—C10D	119.4 (2)	C11B—C12B—H12B	119.2
C9A—C10A—C11A	120.0 (2)	C11C—C12C—H12C	118.9
C9B—C10B—C11B	120.0 (2)	C11D—C12D—H12D	119.3
C6A—C1A—C2A—C3A	−0.9 (3)	ClC—C4C—C5C—C6C	178.10 (16)
C6B—C1B—C2B—C3B	2.9 (3)	ClD—C4D—C5D—C6D	178.99 (17)
C6C—C1C—C2C—C3C	0.2 (3)	C4A—C5A—C6A—C1A	−0.6 (3)
C6D—C1D—C2D—C3D	−0.5 (3)	C4B—C5B—C6B—C1B	−0.8 (3)
C7A—C1A—C2A—C3A	176.1 (2)	C4C—C5C—C6C—C1C	0.6 (3)
C7B—C1B—C2B—C3B	−177.0 (2)	C4D—C5D—C6D—C1D	−0.1 (3)
C7C—C1C—C2C—C3C	−178.0 (2)	C1A—C7A—C8A—C9A	178.7 (2)
C7D—C1D—C2D—C3D	178.6 (2)	C1B—C7B—C8B—C9B	−179.3 (2)
C2A—C1A—C6A—C5A	1.1 (3)	C1C—C7C—C8C—C9C	−178.76 (19)
C2B—C1B—C6B—C5B	−2.0 (3)	C1D—C7D—C8D—C9D	179.8 (2)
C2C—C1C—C6C—C5C	−0.4 (3)	C1A—C7A—C8A—OA	−4.1 (3)
C2D—C1D—C6D—C5D	0.3 (3)	C1B—C7B—C8B—OB	−0.9 (3)
C7A—C1A—C6A—C5A	−175.8 (2)	C1C—C7C—C8C—OC	3.8 (3)
C7B—C1B—C6B—C5B	177.80 (19)	C1D—C7D—C8D—OD	2.3 (3)
C7C—C1C—C6C—C5C	177.7 (2)	C12A—C7A—C8A—C9A	−1.5 (3)
C7D—C1D—C6D—C5D	−178.7 (2)	C12B—C7B—C8B—C9B	−1.4 (3)
C2A—C1A—C7A—C8A	133.5 (2)	C12C—C7C—C8C—C9C	1.1 (3)
C2B—C1B—C7B—C8B	127.7 (2)	C12D—C7D—C8D—C9D	−0.1 (3)
C2C—C1C—C7C—C8C	−130.4 (2)	C12A—C7A—C8A—OA	175.69 (17)
C2D—C1D—C7D—C8D	−120.2 (2)	C12B—C7B—C8B—OB	177.03 (18)
C2A—C1A—C7A—C12A	−46.3 (3)	C12C—C7C—C8C—OC	−176.39 (17)
C2B—C1B—C7B—C12B	−50.1 (3)	C12D—C7D—C8D—OD	−177.61 (18)
C2C—C1C—C7C—C12C	49.7 (3)	C1A—C7A—C12A—C11A	−179.3 (2)
C2D—C1D—C7D—C12D	59.7 (3)	C1B—C7B—C12B—C11B	178.9 (2)
C6A—C1A—C7A—C8A	−49.7 (3)	C1C—C7C—C12C—C11C	179.3 (2)
C6B—C1B—C7B—C8B	−52.1 (3)	C1D—C7D—C12D—C11D	179.4 (2)
C6C—C1C—C7C—C8C	51.5 (3)	C8A—C7A—C12A—C11A	0.9 (3)
C6D—C1D—C7D—C8D	58.8 (3)	C8B—C7B—C12B—C11B	0.9 (3)
C6A—C1A—C7A—C12A	130.5 (2)	C8C—C7C—C12C—C11C	−0.5 (3)
C6B—C1B—C7B—C12B	130.0 (2)	C8D—C7D—C12D—C11D	−0.7 (3)
C6C—C1C—C7C—C12C	−128.4 (2)	C7A—C8A—C9A—C10A	0.4 (3)
C6D—C1D—C7D—C12D	−121.3 (2)	C7B—C8B—C9B—C10B	0.9 (3)
C1A—C2A—C3A—C4A	0.1 (3)	C7C—C8C—C9C—C10C	−0.9 (3)
C1B—C2B—C3B—C4B	−0.8 (3)	C7D—C8D—C9D—C10D	0.7 (3)
C1C—C2C—C3C—C4C	0.0 (3)	OA—C8A—C9A—C10A	−176.60 (18)
C1D—C2D—C3D—C4D	0.5 (3)	OB—C8B—C9B—C10B	−177.38 (19)
C2A—C3A—C4A—C5A	0.4 (3)	OC—C8C—C9C—C10C	176.45 (18)
C2B—C3B—C4B—C5B	−2.3 (3)	OD—C8D—C9D—C10D	178.07 (19)
C2C—C3C—C4C—C5C	0.2 (3)	C8A—C9A—C10A—C11A	1.2 (3)
C2D—C3D—C4D—C5D	−0.3 (4)	C8B—C9B—C10B—C11B	0.0 (3)
C2A—C3A—C4A—ClA	−179.07 (16)	C8C—C9C—C10C—C11C	0.1 (3)
C2B—C3B—C4B—ClB	178.09 (16)	C8D—C9D—C10D—C11D	−0.4 (3)
C2C—C3C—C4C—ClC	−178.38 (17)	C9A—C10A—C11A—C12A	−1.8 (3)
C2D—C3D—C4D—ClD	−179.17 (16)	C9B—C10B—C11B—C12B	−0.4 (4)
C3A—C4A—C5A—C6A	−0.2 (3)	C9C—C10C—C11C—C12C	0.4 (3)
C3B—C4B—C5B—C6B	3.1 (3)	C9D—C10D—C11D—C12D	−0.4 (4)
C3C—C4C—C5C—C6C	−0.5 (3)	C10A—C11A—C12A—C7A	0.7 (3)
C3D—C4D—C5D—C6D	0.2 (4)	C10B—C11B—C12B—C7B	0.0 (4)
ClA—C4A—C5A—C6A	179.28 (16)	C10C—C11C—C12C—C7C	−0.2 (3)
ClB—C4B—C5B—C6B	−177.30 (15)	C10D—C11D—C12D—C7D	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OA—HA···OB	0.82 (2)	2.11 (2)	2.899 (2)	164 (2)
OB—HB···OC	0.81 (2)	2.11 (2)	2.855 (2)	154 (2)
OC—HC···OD	0.79 (2)	1.99 (2)	2.771 (2)	170 (2)
OD—HD···OA	0.84 (3)	2.01 (2)	2.756 (2)	148 (2)