Encapsulated di­chloro­ethane-mediated inter­locked supra­molecular polymeric assembly of A1/A2-dihydroxy-oct­yloxy pillar[5]arene 1,2-di­chloro­ethane monosolvate

The structural and supra­molecular features of a dihy­droxy-functionalized oct­yloxy-pillararene are discussed. In the crystal, the encapsulated 1,2-di­chloro­ethane solvent is stabilized by C—H...π inter­actions and mediates the formation of an inter­locked supra­molecular polymer via C—H...Cl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.049
• wR factor = 0.137
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         18 Note

Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        Cl1 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34B     ..CL1      .       2.90 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.529 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          3 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H14A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14B       Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        50% Note
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C11      - C14      .       1.51 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         24 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015), ShelXle (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2006).

1-(1,4-Dihydroxy)-2,3,4,5-(1,4-dioctyloxy)pillar[5]arene 1,2-dichloroethane solvent

Crystal data

C99H158O10·C2H4Cl2	F(000) = 3528
Mr = 1607.20	Dx = 1.089 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 31.4629 (12) Å	Cell parameters from 11636 reflections
b = 20.2692 (7) Å	θ = 3.1–26.3°
c = 15.3703 (11) Å	µ = 0.12 mm^−1
β = 91.275 (6)°	T = 150 K
V = 9799.7 (9) Å^3	Block, colorless
Z = 4	0.21 × 0.13 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	7023 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.032
ω scans	θmax = 26.3°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −37→39
Tmin = 0.774, Tmax = 0.989	k = −25→24
42520 measured reflections	l = −19→19
9959 independent reflections

Refinement

Refinement on F^2	24 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.064P)^2 + 2.8339P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
9959 reflections	Δρmax = 0.39 e Å^−3
528 parameters	Δρmin = −0.43 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.52608 (3)	0.62986 (5)	0.52918 (7)	0.0395 (3)
Cl1	0.55186 (2)	0.76990 (4)	0.16233 (5)	0.0952 (2)
C51A	0.5073 (3)	0.7445 (4)	0.2239 (6)	0.125 (2)	0.464 (7)
H51A	0.484105	0.759512	0.184099	0.150*	0.464 (7)
H51B	0.508787	0.696374	0.213850	0.150*	0.464 (7)
C51B	0.51449 (18)	0.7915 (3)	0.2421 (5)	0.123 (2)	0.536 (7)
H51C	0.527534	0.769901	0.293884	0.148*	0.536 (7)
H51D	0.521354	0.838850	0.249897	0.148*	0.536 (7)
O2	0.64483 (3)	0.77669 (5)	0.35101 (7)	0.0433 (3)
O3	0.51552 (3)	0.87675 (5)	0.51444 (7)	0.0392 (3)
O4	0.58340 (3)	0.98033 (5)	0.21357 (7)	0.0407 (3)
O5	0.47324 (4)	0.55783 (7)	0.42002 (8)	0.0535 (3)
H5	0.4914 (7)	0.5732 (14)	0.4563 (15)	0.127 (11)*
C1	0.57574 (4)	0.63729 (7)	0.41632 (10)	0.0342 (3)
C2	0.55453 (4)	0.66856 (7)	0.48322 (10)	0.0340 (3)
C3	0.56248 (4)	0.73431 (7)	0.50300 (10)	0.0344 (3)
H3	0.547151	0.754950	0.548068	0.041*
C4	0.59246 (4)	0.77054 (7)	0.45812 (10)	0.0331 (3)
C5	0.61468 (4)	0.73893 (7)	0.39254 (10)	0.0353 (3)
C6	0.60609 (4)	0.67346 (7)	0.37175 (10)	0.0360 (3)
H6	0.621183	0.652917	0.326262	0.043*
C7	0.59975 (5)	0.84281 (7)	0.47991 (10)	0.0363 (3)
H7A	0.592112	0.850730	0.541169	0.044*
H7B	0.630313	0.853176	0.474216	0.044*
C8	0.57387 (4)	0.88849 (7)	0.42128 (10)	0.0330 (3)
C9	0.53189 (4)	0.90490 (7)	0.44047 (10)	0.0334 (3)
C10	0.50904 (5)	0.94760 (7)	0.38618 (10)	0.0335 (3)
H10	0.480914	0.959667	0.400799	0.040*
C11	0.52661 (4)	0.97304 (7)	0.31073 (10)	0.0324 (3)
C12	0.56792 (4)	0.95468 (7)	0.29032 (10)	0.0329 (3)
C13	0.59133 (4)	0.91376 (7)	0.34602 (10)	0.0344 (3)
H13	0.619778	0.902890	0.332339	0.041*
C14	0.500000	1.01589 (10)	0.250000	0.0336 (5)
H14A	0.518806	1.044543	0.215644	0.040*	0.5
H14B	0.481194	1.044544	0.284356	0.040*	0.5
C15	0.48802 (5)	0.56267 (7)	0.33650 (10)	0.0363 (3)
C16	0.53117 (5)	0.56392 (7)	0.31800 (10)	0.0348 (3)
C17	0.54243 (5)	0.56370 (7)	0.23073 (10)	0.0372 (3)
H17	0.571688	0.564275	0.216727	0.045*
C18	0.56560 (5)	0.56684 (7)	0.38916 (10)	0.0378 (4)
H18A	0.556069	0.541780	0.440451	0.045*
H18B	0.591725	0.545572	0.367930	0.045*
C19	0.49696 (5)	0.66342 (7)	0.58421 (10)	0.0384 (3)
H19A	0.478500	0.693143	0.548950	0.046*
H19B	0.512847	0.690397	0.627667	0.046*
C20	0.47014 (5)	0.61268 (8)	0.62986 (11)	0.0410 (4)
H20A	0.488771	0.583358	0.665336	0.049*
H20B	0.454848	0.585243	0.586033	0.049*
C21	0.43810 (5)	0.64623 (7)	0.68835 (10)	0.0387 (4)
H21A	0.416887	0.669869	0.651436	0.046*
H21B	0.453135	0.679399	0.724939	0.046*
C22	0.41490 (5)	0.59824 (8)	0.74739 (11)	0.0410 (4)
H22A	0.400150	0.564782	0.710783	0.049*
H22B	0.436111	0.574949	0.784694	0.049*
C23	0.38255 (5)	0.63133 (8)	0.80523 (10)	0.0408 (4)
H23A	0.358628	0.647936	0.768461	0.049*
H23B	0.396056	0.669711	0.834528	0.049*
C24	0.36519 (5)	0.58494 (8)	0.87401 (11)	0.0440 (4)
H24A	0.353325	0.545278	0.844775	0.053*
H24B	0.388935	0.570446	0.912794	0.053*
C25	0.33098 (6)	0.61590 (10)	0.92887 (12)	0.0547 (5)
H25A	0.306286	0.627359	0.890791	0.066*
H25B	0.342120	0.657311	0.954821	0.066*
C26	0.31624 (6)	0.57082 (11)	1.00130 (12)	0.0643 (6)
H26A	0.340499	0.559481	1.039500	0.077*
H26B	0.304111	0.530447	0.975961	0.077*
H26C	0.294599	0.593494	1.035103	0.077*
C27	0.67085 (5)	0.74467 (9)	0.28883 (11)	0.0453 (4)
H27A	0.652962	0.726534	0.240713	0.054*
H27B	0.686720	0.707865	0.316701	0.054*
C28	0.70150 (5)	0.79524 (9)	0.25407 (12)	0.0503 (4)
H28A	0.717227	0.815997	0.303391	0.060*
H28B	0.685263	0.830239	0.223085	0.060*
C29	0.73314 (5)	0.76452 (10)	0.19214 (12)	0.0519 (5)
H29A	0.750841	0.732111	0.224716	0.062*
H29B	0.717211	0.740314	0.145944	0.062*
C30	0.76207 (5)	0.81448 (10)	0.14993 (14)	0.0607 (5)
H30A	0.776793	0.840235	0.196288	0.073*
H30B	0.744354	0.845558	0.115134	0.073*
C31	0.79542 (5)	0.78446 (11)	0.09109 (13)	0.0595 (5)
H31A	0.815037	0.756882	0.126838	0.071*
H31B	0.781035	0.755310	0.047959	0.071*
C32	0.82113 (6)	0.83584 (11)	0.04310 (14)	0.0687 (6)
H32A	0.834554	0.865875	0.086439	0.082*
H32B	0.801450	0.862480	0.006255	0.082*
C33	0.85581 (6)	0.80769 (12)	−0.01432 (13)	0.0695 (6)
H33A	0.876784	0.783520	0.022559	0.083*
H33B	0.842905	0.775904	−0.056065	0.083*
C34	0.87843 (7)	0.86123 (14)	−0.06413 (18)	0.0942 (9)
H34A	0.858974	0.879893	−0.108306	0.113*
H34B	0.903232	0.842378	−0.092521	0.113*
H34C	0.887728	0.896067	−0.023791	0.113*
C35	0.47133 (5)	0.88783 (8)	0.52980 (10)	0.0373 (3)
H35A	0.454098	0.873954	0.478320	0.045*
H35B	0.466222	0.935390	0.539873	0.045*
C36	0.45850 (5)	0.84864 (8)	0.60853 (10)	0.0409 (4)
H36A	0.478914	0.857214	0.657167	0.049*
H36B	0.459493	0.800958	0.594790	0.049*
C37	0.41377 (5)	0.86709 (8)	0.63631 (11)	0.0420 (4)
H37A	0.413354	0.914617	0.651120	0.050*
H37B	0.393878	0.860306	0.586303	0.050*
C38	0.39779 (5)	0.82805 (8)	0.71365 (11)	0.0427 (4)
H38A	0.393628	0.781509	0.695872	0.051*
H38B	0.419790	0.828902	0.760708	0.051*
C39	0.35635 (5)	0.85437 (8)	0.74903 (11)	0.0444 (4)
H39A	0.361483	0.899063	0.773012	0.053*
H39B	0.335450	0.858617	0.700247	0.053*
C40	0.33716 (5)	0.81172 (8)	0.81929 (10)	0.0399 (4)
H40A	0.359749	0.800269	0.862559	0.048*
H40B	0.326895	0.770091	0.792483	0.048*
C41	0.30058 (5)	0.84390 (9)	0.86639 (12)	0.0497 (4)
H41A	0.310896	0.885039	0.894424	0.060*
H41B	0.278109	0.856038	0.823211	0.060*
C42	0.28144 (6)	0.79983 (11)	0.93509 (13)	0.0605 (5)
H42A	0.303696	0.786316	0.977014	0.073*
H42B	0.269015	0.760640	0.907195	0.073*
H42C	0.259266	0.824090	0.965415	0.073*
C43	0.62086 (5)	0.95076 (8)	0.18009 (11)	0.0402 (4)
H43A	0.617129	0.902359	0.175823	0.048*
H43B	0.645483	0.959865	0.219482	0.048*
C44	0.62861 (5)	0.97944 (8)	0.09101 (11)	0.0419 (4)
H44A	0.631473	1.027953	0.095763	0.050*
H44B	0.603891	0.969841	0.052082	0.050*
C45	0.66860 (5)	0.95097 (9)	0.05176 (11)	0.0459 (4)
H45A	0.664656	0.902882	0.043722	0.055*
H45B	0.692667	0.957418	0.093479	0.055*
C46	0.68018 (5)	0.98138 (9)	−0.03522 (11)	0.0445 (4)
H46A	0.656030	0.975589	−0.076911	0.053*
H46B	0.684781	1.029331	−0.027189	0.053*
C47	0.71981 (5)	0.95118 (9)	−0.07369 (11)	0.0445 (4)
H47A	0.714639	0.903585	−0.083778	0.053*
H47B	0.743532	0.955125	−0.030597	0.053*
C48	0.73333 (5)	0.98252 (9)	−0.15878 (11)	0.0479 (4)
H48A	0.709840	0.977884	−0.202276	0.058*
H48B	0.738095	1.030254	−0.149018	0.058*
C49	0.77328 (5)	0.95275 (10)	−0.19575 (12)	0.0526 (4)
H49A	0.796653	0.956595	−0.151846	0.063*
H49B	0.768337	0.905198	−0.206667	0.063*
C50	0.78709 (7)	0.98497 (12)	−0.27952 (13)	0.0736 (6)
H50A	0.764757	0.979396	−0.324380	0.088*
H50B	0.813378	0.964245	−0.298910	0.088*
H50C	0.792062	1.032112	−0.269421	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0483 (6)	0.0309 (6)	0.0401 (6)	−0.0049 (4)	0.0156 (5)	0.0032 (5)
Cl1	0.0912 (4)	0.0950 (5)	0.1005 (5)	0.0188 (3)	0.0283 (4)	0.0261 (4)
C51A	0.138 (5)	0.078 (4)	0.163 (6)	−0.007 (4)	0.076 (4)	−0.020 (4)
C51B	0.133 (5)	0.076 (4)	0.164 (5)	−0.035 (3)	0.068 (4)	−0.037 (4)
O2	0.0369 (6)	0.0438 (6)	0.0497 (7)	−0.0064 (4)	0.0110 (5)	0.0078 (5)
O3	0.0412 (6)	0.0429 (6)	0.0337 (6)	−0.0041 (4)	0.0065 (4)	0.0063 (5)
O4	0.0408 (6)	0.0406 (6)	0.0410 (6)	0.0016 (4)	0.0100 (5)	0.0117 (5)
O5	0.0490 (7)	0.0694 (9)	0.0427 (7)	−0.0088 (6)	0.0145 (6)	−0.0071 (6)
C1	0.0340 (7)	0.0327 (8)	0.0359 (8)	0.0015 (6)	0.0029 (6)	0.0063 (6)
C2	0.0352 (8)	0.0335 (8)	0.0335 (8)	−0.0037 (6)	0.0037 (6)	0.0079 (6)
C3	0.0372 (8)	0.0351 (8)	0.0309 (8)	−0.0017 (6)	0.0020 (6)	0.0049 (6)
C4	0.0327 (7)	0.0343 (8)	0.0321 (8)	−0.0029 (6)	−0.0050 (6)	0.0077 (6)
C5	0.0307 (7)	0.0389 (9)	0.0364 (9)	−0.0029 (6)	0.0012 (6)	0.0104 (7)
C6	0.0342 (7)	0.0385 (9)	0.0355 (9)	0.0019 (6)	0.0042 (6)	0.0053 (7)
C7	0.0369 (8)	0.0377 (8)	0.0341 (8)	−0.0090 (6)	−0.0030 (6)	0.0038 (7)
C8	0.0360 (8)	0.0297 (8)	0.0332 (8)	−0.0093 (6)	−0.0034 (6)	0.0009 (6)
C9	0.0409 (8)	0.0290 (8)	0.0303 (8)	−0.0088 (6)	0.0030 (6)	−0.0016 (6)
C10	0.0366 (7)	0.0289 (8)	0.0351 (8)	−0.0040 (6)	0.0038 (6)	−0.0032 (6)
C11	0.0388 (8)	0.0239 (7)	0.0344 (8)	−0.0052 (5)	0.0005 (6)	−0.0026 (6)
C12	0.0365 (8)	0.0293 (8)	0.0329 (8)	−0.0083 (6)	0.0031 (6)	0.0027 (6)
C13	0.0331 (7)	0.0325 (8)	0.0378 (9)	−0.0066 (6)	0.0008 (6)	0.0024 (6)
C14	0.0387 (11)	0.0260 (10)	0.0363 (12)	0.000	0.0047 (9)	0.000
C15	0.0422 (8)	0.0298 (8)	0.0374 (9)	−0.0028 (6)	0.0132 (6)	−0.0027 (6)
C16	0.0401 (8)	0.0230 (7)	0.0416 (9)	0.0008 (6)	0.0082 (6)	0.0019 (6)
C17	0.0349 (8)	0.0315 (8)	0.0456 (10)	0.0035 (6)	0.0114 (6)	0.0046 (7)
C18	0.0408 (8)	0.0315 (8)	0.0415 (9)	0.0028 (6)	0.0075 (7)	0.0046 (7)
C19	0.0472 (9)	0.0322 (8)	0.0363 (9)	−0.0031 (6)	0.0106 (7)	0.0005 (7)
C20	0.0501 (9)	0.0333 (8)	0.0402 (9)	−0.0041 (7)	0.0138 (7)	0.0022 (7)
C21	0.0466 (9)	0.0314 (8)	0.0385 (9)	−0.0034 (6)	0.0088 (7)	0.0015 (7)
C22	0.0463 (9)	0.0355 (9)	0.0418 (9)	−0.0043 (6)	0.0121 (7)	0.0004 (7)
C23	0.0440 (9)	0.0409 (9)	0.0380 (9)	−0.0034 (7)	0.0092 (7)	−0.0015 (7)
C24	0.0461 (9)	0.0485 (10)	0.0379 (9)	−0.0108 (7)	0.0096 (7)	−0.0024 (7)
C25	0.0503 (10)	0.0733 (13)	0.0409 (10)	−0.0048 (9)	0.0123 (8)	−0.0020 (9)
C26	0.0587 (11)	0.0906 (16)	0.0444 (11)	−0.0184 (10)	0.0169 (9)	−0.0040 (10)
C27	0.0373 (8)	0.0530 (10)	0.0460 (10)	−0.0031 (7)	0.0104 (7)	0.0058 (8)
C28	0.0367 (8)	0.0550 (11)	0.0595 (12)	−0.0036 (7)	0.0092 (7)	0.0170 (9)
C29	0.0385 (9)	0.0698 (13)	0.0477 (11)	−0.0090 (8)	0.0064 (7)	0.0096 (9)
C30	0.0396 (9)	0.0731 (13)	0.0700 (14)	0.0017 (8)	0.0155 (9)	0.0266 (11)
C31	0.0412 (9)	0.0900 (15)	0.0475 (11)	−0.0105 (9)	0.0049 (8)	0.0104 (10)
C32	0.0406 (10)	0.0929 (16)	0.0732 (14)	0.0043 (9)	0.0163 (9)	0.0312 (12)
C33	0.0476 (11)	0.1114 (18)	0.0497 (12)	−0.0160 (11)	0.0077 (9)	0.0067 (12)
C34	0.0600 (13)	0.125 (2)	0.099 (2)	0.0011 (13)	0.0372 (13)	0.0313 (17)
C35	0.0415 (8)	0.0339 (8)	0.0366 (9)	−0.0028 (6)	0.0074 (6)	−0.0028 (7)
C36	0.0473 (9)	0.0374 (9)	0.0385 (9)	−0.0047 (7)	0.0096 (7)	0.0006 (7)
C37	0.0486 (9)	0.0350 (9)	0.0428 (10)	−0.0019 (7)	0.0111 (7)	−0.0003 (7)
C38	0.0445 (9)	0.0442 (10)	0.0397 (9)	−0.0008 (7)	0.0079 (7)	0.0026 (7)
C39	0.0488 (9)	0.0417 (9)	0.0432 (10)	−0.0013 (7)	0.0111 (7)	−0.0010 (7)
C40	0.0376 (8)	0.0474 (9)	0.0350 (9)	−0.0037 (7)	0.0020 (6)	−0.0005 (7)
C41	0.0451 (9)	0.0561 (11)	0.0484 (11)	−0.0038 (8)	0.0107 (7)	−0.0011 (8)
C42	0.0487 (10)	0.0798 (14)	0.0538 (12)	−0.0054 (9)	0.0149 (8)	0.0059 (10)
C43	0.0346 (8)	0.0426 (9)	0.0436 (10)	−0.0011 (6)	0.0062 (6)	0.0086 (7)
C44	0.0400 (8)	0.0434 (9)	0.0427 (10)	−0.0030 (7)	0.0065 (7)	0.0094 (7)
C45	0.0396 (8)	0.0524 (10)	0.0458 (10)	−0.0008 (7)	0.0071 (7)	0.0111 (8)
C46	0.0416 (9)	0.0476 (10)	0.0446 (10)	−0.0028 (7)	0.0071 (7)	0.0076 (8)
C47	0.0386 (8)	0.0490 (10)	0.0462 (10)	−0.0042 (7)	0.0065 (7)	0.0041 (8)
C48	0.0458 (9)	0.0543 (11)	0.0441 (10)	−0.0056 (7)	0.0076 (7)	0.0013 (8)
C49	0.0509 (10)	0.0589 (11)	0.0484 (11)	−0.0075 (8)	0.0107 (8)	−0.0092 (9)
C50	0.0720 (13)	0.1006 (18)	0.0492 (12)	−0.0119 (12)	0.0220 (10)	−0.0087 (12)

Geometric parameters (Å, º)

O1—C2	1.3942 (16)	C27—C28	1.513 (2)
O1—C19	1.4323 (17)	C27—H27A	0.9900
Cl1—C51B	1.772 (5)	C27—H27B	0.9900
Cl1—C51A	1.785 (5)	C28—C29	1.525 (2)
C51A—C51A^i	0.932 (11)	C28—H28A	0.9900
C51A—H51A	0.9900	C28—H28B	0.9900
C51A—H51B	0.9900	C29—C30	1.517 (2)
C51B—C51B^i	0.949 (9)	C29—H29A	0.9900
C51B—H51C	0.9900	C29—H29B	0.9900
C51B—H51D	0.9900	C30—C31	1.527 (3)
O2—C5	1.3857 (17)	C30—H30A	0.9900
O2—C27	1.4280 (19)	C30—H30B	0.9900
O3—C9	1.3817 (17)	C31—C32	1.520 (2)
O3—C35	1.4332 (17)	C31—H31A	0.9900
O4—C12	1.3873 (17)	C31—H31B	0.9900
O4—C43	1.4282 (18)	C32—C33	1.529 (3)
O5—C15	1.3786 (19)	C32—H32A	0.9900
O5—H5	0.847 (10)	C32—H32B	0.9900
C1—C2	1.391 (2)	C33—C34	1.515 (3)
C1—C6	1.3955 (19)	C33—H33A	0.9900
C1—C18	1.520 (2)	C33—H33B	0.9900
C2—C3	1.388 (2)	C34—H34A	0.9800
C3—C4	1.3905 (19)	C34—H34B	0.9800
C3—H3	0.9500	C34—H34C	0.9800
C4—C5	1.395 (2)	C35—C36	1.510 (2)
C4—C7	1.519 (2)	C35—H35A	0.9900
C5—C6	1.390 (2)	C35—H35B	0.9900
C6—H6	0.9500	C36—C37	1.526 (2)
C7—C8	1.517 (2)	C36—H36A	0.9900
C7—H7A	0.9900	C36—H36B	0.9900
C7—H7B	0.9900	C37—C38	1.523 (2)
C8—C13	1.389 (2)	C37—H37A	0.9900
C8—C9	1.400 (2)	C37—H37B	0.9900
C9—C10	1.391 (2)	C38—C39	1.521 (2)
C10—C11	1.395 (2)	C38—H38A	0.9900
C10—H10	0.9500	C38—H38B	0.9900
C11—C12	1.395 (2)	C39—C40	1.519 (2)
C11—C14	1.5139 (18)	C39—H39A	0.9900
C12—C13	1.391 (2)	C39—H39B	0.9900
C13—H13	0.9500	C40—C41	1.520 (2)
C14—H14A	0.9900	C40—H40A	0.9900
C14—H14B	0.9900	C40—H40B	0.9900
C15—C16	1.394 (2)	C41—C42	1.518 (2)
C15—C17^i	1.394 (2)	C41—H41A	0.9900
C16—C17	1.395 (2)	C41—H41B	0.9900
C16—C18	1.523 (2)	C42—H42A	0.9800
C17—H17	0.9500	C42—H42B	0.9800
C18—H18A	0.9900	C42—H42C	0.9800
C18—H18B	0.9900	C43—C44	1.512 (2)
C19—C20	1.5128 (19)	C43—H43A	0.9900
C19—H19A	0.9900	C43—H43B	0.9900
C19—H19B	0.9900	C44—C45	1.521 (2)
C20—C21	1.526 (2)	C44—H44A	0.9900
C20—H20A	0.9900	C44—H44B	0.9900
C20—H20B	0.9900	C45—C46	1.524 (2)
C21—C22	1.527 (2)	C45—H45A	0.9900
C21—H21A	0.9900	C45—H45B	0.9900
C21—H21B	0.9900	C46—C47	1.520 (2)
C22—C23	1.522 (2)	C46—H46A	0.9900
C22—H22A	0.9900	C46—H46B	0.9900
C22—H22B	0.9900	C47—C48	1.523 (2)
C23—C24	1.525 (2)	C47—H47A	0.9900
C23—H23A	0.9900	C47—H47B	0.9900
C23—H23B	0.9900	C48—C49	1.516 (2)
C24—C25	1.518 (2)	C48—H48A	0.9900
C24—H24A	0.9900	C48—H48B	0.9900
C24—H24B	0.9900	C49—C50	1.516 (3)
C25—C26	1.521 (3)	C49—H49A	0.9900
C25—H25A	0.9900	C49—H49B	0.9900
C25—H25B	0.9900	C50—H50A	0.9800
C26—H26A	0.9800	C50—H50B	0.9800
C26—H26B	0.9800	C50—H50C	0.9800
C26—H26C	0.9800
C2—O1—C19	117.27 (11)	C29—C28—H28A	109.2
C51A^i—C51A—Cl1	149.8 (14)	C27—C28—H28B	109.2
C51A^i—C51A—H51A	99.2	C29—C28—H28B	109.2
Cl1—C51A—H51A	99.2	H28A—C28—H28B	107.9
C51A^i—C51A—H51B	99.2	C30—C29—C28	113.61 (16)
Cl1—C51A—H51B	99.2	C30—C29—H29A	108.8
H51A—C51A—H51B	104.0	C28—C29—H29A	108.8
C51B^i—C51B—Cl1	146.5 (11)	C30—C29—H29B	108.8
C51B^i—C51B—H51C	100.2	C28—C29—H29B	108.8
Cl1—C51B—H51C	100.2	H29A—C29—H29B	107.7
C51B^i—C51B—H51D	100.2	C29—C30—C31	114.46 (17)
Cl1—C51B—H51D	100.2	C29—C30—H30A	108.6
H51C—C51B—H51D	104.2	C31—C30—H30A	108.6
C5—O2—C27	117.77 (12)	C29—C30—H30B	108.6
C9—O3—C35	116.85 (12)	C31—C30—H30B	108.6
C12—O4—C43	117.21 (11)	H30A—C30—H30B	107.6
C15—O5—H5	111 (2)	C32—C31—C30	113.23 (18)
C2—C1—C6	117.92 (14)	C32—C31—H31A	108.9
C2—C1—C18	122.00 (13)	C30—C31—H31A	108.9
C6—C1—C18	120.04 (13)	C32—C31—H31B	108.9
C3—C2—C1	120.80 (13)	C30—C31—H31B	108.9
C3—C2—O1	122.95 (13)	H31A—C31—H31B	107.7
C1—C2—O1	116.24 (13)	C31—C32—C33	114.76 (19)
C2—C3—C4	121.29 (14)	C31—C32—H32A	108.6
C2—C3—H3	119.4	C33—C32—H32A	108.6
C4—C3—H3	119.4	C31—C32—H32B	108.6
C3—C4—C5	118.17 (13)	C33—C32—H32B	108.6
C3—C4—C7	120.05 (14)	H32A—C32—H32B	107.6
C5—C4—C7	121.77 (13)	C34—C33—C32	111.9 (2)
O2—C5—C6	123.57 (14)	C34—C33—H33A	109.2
O2—C5—C4	116.00 (13)	C32—C33—H33A	109.2
C6—C5—C4	120.43 (13)	C34—C33—H33B	109.2
C5—C6—C1	121.35 (14)	C32—C33—H33B	109.2
C5—C6—H6	119.3	H33A—C33—H33B	107.9
C1—C6—H6	119.3	C33—C34—H34A	109.5
C8—C7—C4	112.41 (12)	C33—C34—H34B	109.5
C8—C7—H7A	109.1	H34A—C34—H34B	109.5
C4—C7—H7A	109.1	C33—C34—H34C	109.5
C8—C7—H7B	109.1	H34A—C34—H34C	109.5
C4—C7—H7B	109.1	H34B—C34—H34C	109.5
H7A—C7—H7B	107.9	O3—C35—C36	109.10 (13)
C13—C8—C9	118.69 (14)	O3—C35—H35A	109.9
C13—C8—C7	120.19 (13)	C36—C35—H35A	109.9
C9—C8—C7	121.10 (13)	O3—C35—H35B	109.9
O3—C9—C10	123.59 (13)	C36—C35—H35B	109.9
O3—C9—C8	116.49 (13)	H35A—C35—H35B	108.3
C10—C9—C8	119.92 (13)	C35—C36—C37	111.09 (13)
C9—C10—C11	121.32 (13)	C35—C36—H36A	109.4
C9—C10—H10	119.3	C37—C36—H36A	109.4
C11—C10—H10	119.3	C35—C36—H36B	109.4
C10—C11—C12	118.49 (13)	C37—C36—H36B	109.4
C10—C11—C14	120.06 (12)	H36A—C36—H36B	108.0
C12—C11—C14	121.32 (12)	C38—C37—C36	114.43 (14)
O4—C12—C13	123.76 (13)	C38—C37—H37A	108.7
O4—C12—C11	115.97 (13)	C36—C37—H37A	108.7
C13—C12—C11	120.26 (13)	C38—C37—H37B	108.7
C8—C13—C12	121.24 (13)	C36—C37—H37B	108.7
C8—C13—H13	119.4	H37A—C37—H37B	107.6
C12—C13—H13	119.4	C39—C38—C37	113.42 (14)
C11—C14—C11^i	109.98 (16)	C39—C38—H38A	108.9
C11—C14—H14A	109.7	C37—C38—H38A	108.9
C11^i—C14—H14A	109.7	C39—C38—H38B	108.9
C11—C14—H14B	109.7	C37—C38—H38B	108.9
C11^i—C14—H14B	109.7	H38A—C38—H38B	107.7
H14A—C14—H14B	108.2	C40—C39—C38	114.34 (14)
O5—C15—C16	122.80 (15)	C40—C39—H39A	108.7
O5—C15—C17^i	116.80 (13)	C38—C39—H39A	108.7
C16—C15—C17^i	120.35 (14)	C40—C39—H39B	108.7
C15—C16—C17	117.74 (14)	C38—C39—H39B	108.7
C15—C16—C18	122.32 (14)	H39A—C39—H39B	107.6
C17—C16—C18	119.93 (13)	C39—C40—C41	114.30 (14)
C15^i—C17—C16	121.87 (13)	C39—C40—H40A	108.7
C15^i—C17—H17	119.1	C41—C40—H40A	108.7
C16—C17—H17	119.1	C39—C40—H40B	108.7
C1—C18—C16	112.06 (12)	C41—C40—H40B	108.7
C1—C18—H18A	109.2	H40A—C40—H40B	107.6
C16—C18—H18A	109.2	C42—C41—C40	113.27 (15)
C1—C18—H18B	109.2	C42—C41—H41A	108.9
C16—C18—H18B	109.2	C40—C41—H41A	108.9
H18A—C18—H18B	107.9	C42—C41—H41B	108.9
O1—C19—C20	108.77 (12)	C40—C41—H41B	108.9
O1—C19—H19A	109.9	H41A—C41—H41B	107.7
C20—C19—H19A	109.9	C41—C42—H42A	109.5
O1—C19—H19B	109.9	C41—C42—H42B	109.5
C20—C19—H19B	109.9	H42A—C42—H42B	109.5
H19A—C19—H19B	108.3	C41—C42—H42C	109.5
C19—C20—C21	110.68 (12)	H42A—C42—H42C	109.5
C19—C20—H20A	109.5	H42B—C42—H42C	109.5
C21—C20—H20A	109.5	O4—C43—C44	108.42 (12)
C19—C20—H20B	109.5	O4—C43—H43A	110.0
C21—C20—H20B	109.5	C44—C43—H43A	110.0
H20A—C20—H20B	108.1	O4—C43—H43B	110.0
C20—C21—C22	113.40 (12)	C44—C43—H43B	110.0
C20—C21—H21A	108.9	H43A—C43—H43B	108.4
C22—C21—H21A	108.9	C43—C44—C45	111.40 (13)
C20—C21—H21B	108.9	C43—C44—H44A	109.3
C22—C21—H21B	108.9	C45—C44—H44A	109.3
H21A—C21—H21B	107.7	C43—C44—H44B	109.3
C23—C22—C21	113.65 (13)	C45—C44—H44B	109.3
C23—C22—H22A	108.8	H44A—C44—H44B	108.0
C21—C22—H22A	108.8	C44—C45—C46	114.25 (14)
C23—C22—H22B	108.8	C44—C45—H45A	108.7
C21—C22—H22B	108.8	C46—C45—H45A	108.7
H22A—C22—H22B	107.7	C44—C45—H45B	108.7
C22—C23—C24	112.81 (13)	C46—C45—H45B	108.7
C22—C23—H23A	109.0	H45A—C45—H45B	107.6
C24—C23—H23A	109.0	C47—C46—C45	113.11 (14)
C22—C23—H23B	109.0	C47—C46—H46A	109.0
C24—C23—H23B	109.0	C45—C46—H46A	109.0
H23A—C23—H23B	107.8	C47—C46—H46B	109.0
C25—C24—C23	113.55 (15)	C45—C46—H46B	109.0
C25—C24—H24A	108.9	H46A—C46—H46B	107.8
C23—C24—H24A	108.9	C46—C47—C48	114.40 (14)
C25—C24—H24B	108.9	C46—C47—H47A	108.7
C23—C24—H24B	108.9	C48—C47—H47A	108.7
H24A—C24—H24B	107.7	C46—C47—H47B	108.7
C24—C25—C26	112.95 (17)	C48—C47—H47B	108.7
C24—C25—H25A	109.0	H47A—C47—H47B	107.6
C26—C25—H25A	109.0	C49—C48—C47	113.93 (15)
C24—C25—H25B	109.0	C49—C48—H48A	108.8
C26—C25—H25B	109.0	C47—C48—H48A	108.8
H25A—C25—H25B	107.8	C49—C48—H48B	108.8
C25—C26—H26A	109.5	C47—C48—H48B	108.8
C25—C26—H26B	109.5	H48A—C48—H48B	107.7
H26A—C26—H26B	109.5	C50—C49—C48	113.74 (17)
C25—C26—H26C	109.5	C50—C49—H49A	108.8
H26A—C26—H26C	109.5	C48—C49—H49A	108.8
H26B—C26—H26C	109.5	C50—C49—H49B	108.8
O2—C27—C28	107.93 (14)	C48—C49—H49B	108.8
O2—C27—H27A	110.1	H49A—C49—H49B	107.7
C28—C27—H27A	110.1	C49—C50—H50A	109.5
O2—C27—H27B	110.1	C49—C50—H50B	109.5
C28—C27—H27B	110.1	H50A—C50—H50B	109.5
H27A—C27—H27B	108.4	C49—C50—H50C	109.5
C27—C28—C29	111.95 (15)	H50A—C50—H50C	109.5
C27—C28—H28A	109.2	H50B—C50—H50C	109.5
C6—C1—C2—C3	1.9 (2)	O4—C12—C13—C8	−178.75 (13)
C18—C1—C2—C3	−175.80 (14)	C11—C12—C13—C8	2.2 (2)
C6—C1—C2—O1	−176.77 (12)	C10—C11—C14—C11^i	−83.32 (12)
C18—C1—C2—O1	5.5 (2)	C12—C11—C14—C11^i	92.57 (13)
C19—O1—C2—C3	15.2 (2)	O5—C15—C16—C17	175.06 (13)
C19—O1—C2—C1	−166.12 (13)	C17^i—C15—C16—C17	−2.36 (19)
C1—C2—C3—C4	−1.4 (2)	O5—C15—C16—C18	−6.2 (2)
O1—C2—C3—C4	177.16 (13)	C17^i—C15—C16—C18	176.41 (13)
C2—C3—C4—C5	−0.3 (2)	C15—C16—C17—C15^i	0.37 (19)
C2—C3—C4—C7	178.65 (13)	C18—C16—C17—C15^i	−178.43 (13)
C27—O2—C5—C6	−5.6 (2)	C2—C1—C18—C16	90.31 (17)
C27—O2—C5—C4	174.64 (13)	C6—C1—C18—C16	−87.37 (16)
C3—C4—C5—O2	−178.67 (12)	C15—C16—C18—C1	−87.07 (17)
C7—C4—C5—O2	2.4 (2)	C17—C16—C18—C1	91.68 (16)
C3—C4—C5—C6	1.5 (2)	C2—O1—C19—C20	−178.21 (12)
C7—C4—C5—C6	−177.41 (13)	O1—C19—C20—C21	−179.15 (13)
O2—C5—C6—C1	179.18 (13)	C19—C20—C21—C22	−170.72 (14)
C4—C5—C6—C1	−1.0 (2)	C20—C21—C22—C23	−179.39 (14)
C2—C1—C6—C5	−0.7 (2)	C21—C22—C23—C24	−170.36 (14)
C18—C1—C6—C5	177.07 (13)	C22—C23—C24—C25	−176.61 (14)
C3—C4—C7—C8	−94.67 (16)	C23—C24—C25—C26	−175.88 (14)
C5—C4—C7—C8	84.26 (17)	C5—O2—C27—C28	−178.92 (13)
C4—C7—C8—C13	−92.92 (16)	O2—C27—C28—C29	175.51 (14)
C4—C7—C8—C9	85.65 (17)	C27—C28—C29—C30	175.15 (15)
C35—O3—C9—C10	6.3 (2)	C28—C29—C30—C31	177.17 (16)
C35—O3—C9—C8	−173.83 (12)	C29—C30—C31—C32	174.53 (16)
C13—C8—C9—O3	177.87 (12)	C30—C31—C32—C33	178.18 (17)
C7—C8—C9—O3	−0.7 (2)	C31—C32—C33—C34	176.70 (19)
C13—C8—C9—C10	−2.2 (2)	C9—O3—C35—C36	175.07 (12)
C7—C8—C9—C10	179.17 (13)	O3—C35—C36—C37	170.97 (12)
O3—C9—C10—C11	−177.94 (13)	C35—C36—C37—C38	178.06 (13)
C8—C9—C10—C11	2.2 (2)	C36—C37—C38—C39	170.93 (14)
C9—C10—C11—C12	0.1 (2)	C37—C38—C39—C40	173.32 (14)
C9—C10—C11—C14	176.09 (13)	C38—C39—C40—C41	169.14 (14)
C43—O4—C12—C13	15.6 (2)	C39—C40—C41—C42	178.94 (15)
C43—O4—C12—C11	−165.35 (12)	C12—O4—C43—C44	172.32 (12)
C10—C11—C12—O4	178.63 (12)	O4—C43—C44—C45	179.04 (13)
C14—C11—C12—O4	2.7 (2)	C43—C44—C45—C46	−175.75 (14)
C10—C11—C12—C13	−2.2 (2)	C44—C45—C46—C47	−178.99 (14)
C14—C11—C12—C13	−178.20 (13)	C45—C46—C47—C48	−177.51 (14)
C9—C8—C13—C12	0.1 (2)	C46—C47—C48—C49	179.06 (14)
C7—C8—C13—C12	178.69 (13)	C47—C48—C49—C50	−178.88 (15)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.85 (2)	1.93 (2)	2.754 (2)	165 (2)
C34^ii—H34B^ii···Cl1	0.98	2.90	3.782 (3)	151

Symmetry code: (ii) −x+3/2, −y+3/2, −z.