Crystal structure of 2,2′′-bis­(2,7-di­chloro-9-hy­droxy-9H-fluoren-9-yl)-1,1′:4′,1′′-terphenyl tri­ethyl­amine trisolvate

In the crystal structure of 2,2′′-bis­(2,7-di­chloro-9-hy­droxy-9-fluoren­yl)-1,1′:4′,1′′-terphenyl as the tris­(tri­ethyl­amine) solvate, the diol host mol­ecule possesses a `folded' mol­ecular conformation with inversion symmetry. Two of the three solvent mol­ecules form O—H...N hydrogen bonds and the third one forms C—H...N hydrogen bonds with the host compound.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.040
• wR factor = 0.113
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT223_ALERT_4_B Large Solvent/Anion H    Ueq(max)/Ueq(min) .....        4.2 Ratio

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2D6   ..  CL2A    ..       2.90 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         28 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records         24 Report
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)   C5DA   --  C6DA    ..        6.8 su
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =         67 Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (  12.47) in Resd. #          3 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (  11.07) in Resd. #          5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   9.53) in Resd. #          6 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (  10.93) in Resd. #          7 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         89 Note
PLAT793_ALERT_4_G The Model has Chirality at C13     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C13A    (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         24 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Sheldrick, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2,2''-Bis(2,7-dichloro-9-hydroxy-9H-fluoren-9-yl)-1,1':4',1''-terphenyl triethylamine trisolvate

Crystal data

C44H26Cl4O2·3C6H15N	Z = 2
Mr = 1032.01	F(000) = 1096
Triclinic, P1	Dx = 1.224 Mg m^−3
a = 14.5995 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8094 (2) Å	Cell parameters from 9853 reflections
c = 15.7705 (3) Å	θ = 2.4–31.3°
α = 68.373 (1)°	µ = 0.26 mm^−1
β = 66.837 (1)°	T = 100 K
γ = 67.558 (1)°	Plate, colourless
V = 2800.13 (8) Å^3	0.42 × 0.40 × 0.23 mm

Data collection

Bruker CCD area detector diffractometer	11477 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 28.4°, θmin = 1.5°
Tmin = 0.900, Tmax = 0.943	h = −19→19
53831 measured reflections	k = −19→19
14031 independent reflections	l = −21→21

Refinement

Refinement on F^2	24 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 1.6165P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
14031 reflections	Δρmax = 0.59 e Å^−3
773 parameters	Δρmin = −0.59 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.60638 (3)	0.02641 (3)	0.36155 (3)	0.02782 (9)
Cl2	0.59812 (3)	0.31311 (3)	−0.33671 (3)	0.02962 (9)
O1	0.78230 (7)	0.18376 (8)	−0.03539 (7)	0.0199 (2)
H1	0.7514	0.2398	−0.0220	0.030*
C1	0.63440 (10)	0.12716 (10)	0.08381 (9)	0.0163 (2)
C2	0.65868 (10)	0.07862 (10)	0.16874 (10)	0.0188 (3)
H2	0.7279	0.0419	0.1697	0.023*
C3	0.57796 (11)	0.08549 (11)	0.25318 (10)	0.0199 (3)
C4	0.47565 (10)	0.13766 (11)	0.25341 (10)	0.0207 (3)
H4	0.4220	0.1398	0.3120	0.025*
C5	0.45285 (10)	0.18656 (11)	0.16705 (10)	0.0198 (3)
H5	0.3835	0.2226	0.1661	0.024*
C6	0.53259 (10)	0.18211 (10)	0.08225 (10)	0.0171 (3)
C7	0.53127 (10)	0.22501 (10)	−0.01767 (10)	0.0177 (3)
C8	0.45058 (11)	0.28265 (11)	−0.05765 (11)	0.0225 (3)
H8	0.3818	0.3026	−0.0180	0.027*
C9	0.47169 (12)	0.31085 (11)	−0.15657 (11)	0.0250 (3)
H9	0.4175	0.3500	−0.1851	0.030*
C10	0.57288 (12)	0.28102 (11)	−0.21279 (10)	0.0221 (3)
C11	0.65509 (11)	0.22404 (10)	−0.17454 (10)	0.0196 (3)
H11	0.7240	0.2051	−0.2144	0.024*
C12	0.63267 (10)	0.19620 (10)	−0.07658 (10)	0.0172 (3)
C13	0.70829 (10)	0.13336 (10)	−0.01747 (9)	0.0163 (2)
C14	0.76933 (10)	0.03037 (10)	−0.04016 (9)	0.0180 (3)
C15	0.87711 (11)	0.00223 (11)	−0.06259 (10)	0.0220 (3)
H15	0.9098	0.0451	−0.0596	0.026*
C16	0.93772 (12)	−0.08693 (12)	−0.08910 (11)	0.0288 (3)
H16	1.0111	−0.1043	−0.1046	0.035*
C17	0.89114 (13)	−0.15025 (13)	−0.09285 (13)	0.0339 (4)
H17	0.9321	−0.2113	−0.1111	0.041*
C18	0.78417 (13)	−0.12403 (12)	−0.06975 (12)	0.0297 (3)
H18	0.7526	−0.1680	−0.0724	0.036*
C19	0.72127 (11)	−0.03479 (11)	−0.04260 (10)	0.0211 (3)
C20	0.60696 (11)	−0.01430 (10)	−0.02017 (10)	0.0201 (3)
C21	0.54278 (11)	−0.03021 (11)	0.07381 (10)	0.0212 (3)
H21	0.5716	−0.0514	0.1249	0.025*
C22	0.43748 (11)	−0.01550 (11)	0.09362 (10)	0.0216 (3)
H22	0.3950	−0.0258	0.1580	0.026*
Cl1A	0.92106 (3)	0.86051 (4)	0.13781 (3)	0.03593 (11)
Cl2A	0.87208 (4)	0.64484 (3)	0.84734 (3)	0.04199 (12)
O1A	0.71671 (7)	0.87036 (7)	0.52729 (7)	0.01877 (19)
H1A	0.7474	0.9119	0.5195	0.028*
C1A	0.87109 (10)	0.78873 (10)	0.41745 (10)	0.0163 (2)
C2A	0.85448 (10)	0.81792 (10)	0.32984 (10)	0.0186 (3)
H2A	0.7870	0.8343	0.3246	0.022*
C3A	0.94014 (11)	0.82247 (11)	0.24930 (10)	0.0219 (3)
C4A	1.04014 (11)	0.79780 (11)	0.25515 (11)	0.0237 (3)
H4A	1.0974	0.7998	0.1989	0.028*
C5A	1.05506 (10)	0.77022 (11)	0.34418 (11)	0.0213 (3)
H5A	1.1225	0.7541	0.3494	0.026*
C6A	0.97026 (10)	0.76652 (10)	0.42527 (10)	0.0178 (3)
C7A	0.96262 (11)	0.73781 (10)	0.52698 (10)	0.0192 (3)
C8A	1.03705 (12)	0.71089 (11)	0.57298 (12)	0.0265 (3)
H8A	1.1068	0.7106	0.5373	0.032*
C9A	1.00714 (13)	0.68452 (12)	0.67219 (12)	0.0308 (4)
H9A	1.0565	0.6669	0.7049	0.037*
C10A	0.90563 (13)	0.68397 (12)	0.72328 (11)	0.0284 (3)
C11A	0.82964 (12)	0.71172 (11)	0.67874 (11)	0.0239 (3)
H11A	0.7600	0.7116	0.7147	0.029*
C12A	0.85985 (11)	0.73933 (10)	0.58041 (10)	0.0184 (3)
C13A	0.79079 (10)	0.77627 (10)	0.51543 (9)	0.0162 (2)
C14A	0.73042 (10)	0.70199 (10)	0.53606 (9)	0.0166 (2)
C15A	0.62299 (10)	0.73819 (11)	0.55279 (10)	0.0199 (3)
H15A	0.5905	0.8085	0.5461	0.024*
C16A	0.56284 (11)	0.67338 (12)	0.57902 (11)	0.0245 (3)
H16A	0.4899	0.6995	0.5902	0.029*
C17A	0.60905 (11)	0.57107 (12)	0.58886 (11)	0.0269 (3)
H17A	0.5681	0.5262	0.6082	0.032*
C18A	0.71616 (11)	0.53410 (11)	0.57025 (11)	0.0238 (3)
H18A	0.7478	0.4637	0.5765	0.029*
C19A	0.77833 (10)	0.59803 (10)	0.54256 (9)	0.0175 (3)
C20A	0.89299 (10)	0.55012 (10)	0.52056 (10)	0.0167 (2)
C21A	0.95553 (10)	0.55419 (10)	0.42644 (10)	0.0186 (3)
H21A	0.9256	0.5909	0.3756	0.022*
C22A	1.06098 (10)	0.50521 (10)	0.40625 (10)	0.0186 (3)
H22A	1.1023	0.5094	0.3417	0.022*
N1B	0.21028 (9)	0.98034 (9)	0.47727 (9)	0.0206 (2)
C1B	0.11268 (11)	0.96584 (13)	0.55043 (11)	0.0272 (3)
H1B1	0.0968	0.9098	0.5440	0.033*
H1B2	0.0559	1.0279	0.5385	0.033*
C2B	0.11490 (14)	0.94238 (14)	0.65192 (12)	0.0339 (4)
H2B1	0.1588	0.8735	0.6697	0.051*
H2B2	0.0443	0.9479	0.6955	0.051*
H2B3	0.1430	0.9905	0.6561	0.051*
C3B	0.19718 (12)	1.02007 (11)	0.38051 (11)	0.0238 (3)
H3B1	0.2584	1.0438	0.3357	0.029*
H3B2	0.1358	1.0798	0.3810	0.029*
C4B	0.18392 (13)	0.94741 (13)	0.34101 (12)	0.0294 (3)
H4B1	0.2465	0.8903	0.3347	0.044*
H4B2	0.1726	0.9829	0.2783	0.044*
H4B3	0.1241	0.9224	0.3847	0.044*
C5B	0.29651 (11)	0.88733 (11)	0.48674 (11)	0.0239 (3)
H5B1	0.2804	0.8329	0.4777	0.029*
H5B2	0.3021	0.8660	0.5523	0.029*
C6B	0.40009 (12)	0.89960 (13)	0.41604 (12)	0.0298 (3)
H6B1	0.3980	0.9125	0.3512	0.045*
H6B2	0.4549	0.8376	0.4300	0.045*
H6B3	0.4144	0.9566	0.4212	0.045*
N1C	0.7405 (9)	0.5936 (6)	0.2422 (6)	0.0241 (7)	0.433 (3)
C1C	0.7208 (4)	0.5371 (4)	0.3433 (3)	0.0351 (10)	0.433 (3)
H1C1	0.6697	0.5835	0.3830	0.042*	0.433 (3)
H1C2	0.7860	0.5122	0.3607	0.042*	0.433 (3)
C2C	0.6805 (5)	0.4481 (6)	0.3656 (7)	0.0465 (19)	0.433 (3)
H2C1	0.6252	0.4693	0.3362	0.070*	0.433 (3)
H2C2	0.6531	0.4236	0.4349	0.070*	0.433 (3)
H2C3	0.7372	0.3937	0.3403	0.070*	0.433 (3)
C3C	0.7547 (3)	0.6915 (3)	0.2294 (3)	0.0287 (9)	0.433 (3)
H3C1	0.7755	0.7248	0.1603	0.034*	0.433 (3)
H3C2	0.8118	0.6794	0.2547	0.034*	0.433 (3)
C4C	0.6581 (11)	0.7621 (9)	0.2788 (9)	0.032 (2)	0.433 (3)
H4C1	0.5981	0.7635	0.2644	0.048*	0.433 (3)
H4C2	0.6667	0.8304	0.2560	0.048*	0.433 (3)
H4C3	0.6472	0.7382	0.3479	0.048*	0.433 (3)
C5C	0.8334 (3)	0.5338 (3)	0.1848 (3)	0.0249 (9)	0.433 (3)
H5C1	0.8277	0.4643	0.2023	0.030*	0.433 (3)
H5C2	0.8950	0.5294	0.1999	0.030*	0.433 (3)
C6C	0.8489 (12)	0.5789 (8)	0.0782 (6)	0.0329 (16)	0.433 (3)
H6C1	0.7852	0.5905	0.0638	0.049*	0.433 (3)
H6C2	0.9061	0.5319	0.0433	0.049*	0.433 (3)
H6C3	0.8653	0.6432	0.0587	0.049*	0.433 (3)
N1CA	0.7332 (7)	0.5984 (5)	0.2574 (5)	0.0241 (7)	0.567 (3)
C1CA	0.7446 (3)	0.4958 (3)	0.3206 (3)	0.0325 (8)	0.567 (3)
H1C3	0.7813	0.4879	0.3652	0.039*	0.567 (3)
H1C4	0.7883	0.4467	0.2816	0.039*	0.567 (3)
C2CA	0.6425 (4)	0.4705 (4)	0.3782 (5)	0.0396 (11)	0.567 (3)
H2C4	0.5999	0.5168	0.4192	0.059*	0.567 (3)
H2C5	0.6558	0.4008	0.4178	0.059*	0.567 (3)
H2C6	0.6059	0.4775	0.3347	0.059*	0.567 (3)
C3CA	0.6975 (2)	0.6728 (2)	0.3129 (2)	0.0286 (7)	0.567 (3)
H3C3	0.7560	0.6695	0.3319	0.034*	0.567 (3)
H3C4	0.6424	0.6543	0.3719	0.034*	0.567 (3)
C4CA	0.6558 (9)	0.7806 (7)	0.2589 (7)	0.0307 (17)	0.567 (3)
H4C4	0.7103	0.8000	0.2009	0.046*	0.567 (3)
H4C5	0.6338	0.8262	0.2995	0.046*	0.567 (3)
H4C6	0.5965	0.7850	0.2415	0.046*	0.567 (3)
C5CA	0.8318 (2)	0.6070 (3)	0.1833 (2)	0.0359 (8)	0.567 (3)
H5C3	0.8891	0.5724	0.2128	0.043*	0.567 (3)
H5C4	0.8303	0.6793	0.1563	0.043*	0.567 (3)
C6CA	0.8528 (10)	0.5612 (7)	0.1033 (5)	0.0468 (19)	0.567 (3)
H6C4	0.8599	0.4885	0.1289	0.070*	0.567 (3)
H6C5	0.9171	0.5720	0.0539	0.070*	0.567 (3)
H6C6	0.7951	0.5935	0.0755	0.070*	0.567 (3)
N1D	0.7016 (5)	0.3706 (6)	1.0068 (3)	0.0238 (9)	0.497 (3)
C1D	0.6422 (3)	0.4484 (3)	0.9448 (3)	0.0369 (9)	0.497 (3)
H1D1	0.6234	0.5137	0.9597	0.044*	0.497 (3)
H1D2	0.5770	0.4322	0.9592	0.044*	0.497 (3)
C2D	0.6979 (5)	0.4605 (4)	0.8397 (4)	0.0554 (14)	0.497 (3)
H2D1	0.7587	0.4838	0.8232	0.083*	0.497 (3)
H2D2	0.6510	0.5101	0.8029	0.083*	0.497 (3)
H2D3	0.7203	0.3953	0.8248	0.083*	0.497 (3)
C3D	0.6371 (4)	0.3527 (3)	1.1070 (3)	0.0395 (10)	0.497 (3)
H3D1	0.6761	0.2907	1.1443	0.047*	0.497 (3)
H3D2	0.5743	0.3391	1.1102	0.047*	0.497 (3)
C4D	0.6026 (4)	0.4366 (3)	1.1557 (3)	0.0509 (12)	0.497 (3)
H4D1	0.6630	0.4437	1.1628	0.076*	0.497 (3)
H4D2	0.5532	0.4200	1.2188	0.076*	0.497 (3)
H4D3	0.5692	0.5004	1.1169	0.076*	0.497 (3)
C5D	0.7959 (5)	0.3981 (8)	0.9893 (7)	0.056 (4)	0.497 (3)
H5D1	0.8162	0.3669	1.0490	0.067*	0.497 (3)
H5D2	0.7756	0.4722	0.9797	0.067*	0.497 (3)
C6D	0.8967 (2)	0.3713 (3)	0.9051 (3)	0.0386 (9)	0.497 (3)
H6D1	0.9136	0.3001	0.9067	0.058*	0.497 (3)
H6D2	0.9546	0.3831	0.9123	0.058*	0.497 (3)
H6D3	0.8845	0.4141	0.8440	0.058*	0.497 (3)
N1DA	0.7094 (5)	0.3795 (6)	0.9764 (3)	0.0238 (9)	0.503 (3)
C1DA	0.6889 (3)	0.4252 (3)	0.8834 (3)	0.0280 (8)	0.503 (3)
H1D3	0.6261	0.4101	0.8888	0.034*	0.503 (3)
H1D4	0.7475	0.3912	0.8365	0.034*	0.503 (3)
C2DA	0.6733 (3)	0.5392 (2)	0.8428 (3)	0.0366 (9)	0.503 (3)
H2D4	0.6176	0.5744	0.8892	0.055*	0.503 (3)
H2D5	0.6548	0.5611	0.7835	0.055*	0.503 (3)
H2D6	0.7377	0.5551	0.8296	0.055*	0.503 (3)
C3DA	0.6148 (3)	0.4082 (3)	1.0529 (3)	0.0336 (8)	0.503 (3)
H3D3	0.5569	0.3955	1.0455	0.040*	0.503 (3)
H3D4	0.5973	0.4817	1.0456	0.040*	0.503 (3)
C4DA	0.6240 (4)	0.3518 (4)	1.1529 (3)	0.0454 (11)	0.503 (3)
H4D4	0.6519	0.2791	1.1577	0.068*	0.503 (3)
H4D5	0.5554	0.3651	1.1996	0.068*	0.503 (3)
H4D6	0.6707	0.3748	1.1658	0.068*	0.503 (3)
C5DA	0.7983 (5)	0.3993 (5)	0.9831 (4)	0.025 (2)	0.503 (3)
H5D3	0.7715	0.4619	1.0048	0.030*	0.503 (3)
H5D4	0.8463	0.4135	0.9179	0.030*	0.503 (3)
C6DA	0.8645 (4)	0.3148 (4)	1.0504 (5)	0.085 (2)	0.503 (3)
H6D4	0.8256	0.3145	1.1172	0.127*	0.503 (3)
H6D5	0.9303	0.3293	1.0345	0.127*	0.503 (3)
H6D6	0.8784	0.2485	1.0408	0.127*	0.503 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02612 (17)	0.0363 (2)	0.01956 (17)	−0.00544 (15)	−0.00797 (13)	−0.00754 (14)
Cl2	0.0435 (2)	0.02378 (18)	0.02120 (17)	−0.00960 (16)	−0.01303 (15)	−0.00132 (14)
O1	0.0167 (4)	0.0196 (5)	0.0260 (5)	−0.0077 (4)	−0.0024 (4)	−0.0100 (4)
C1	0.0167 (6)	0.0149 (6)	0.0184 (6)	−0.0050 (5)	−0.0030 (5)	−0.0072 (5)
C2	0.0169 (6)	0.0189 (7)	0.0210 (7)	−0.0038 (5)	−0.0049 (5)	−0.0077 (5)
C3	0.0224 (6)	0.0214 (7)	0.0175 (6)	−0.0059 (5)	−0.0064 (5)	−0.0061 (5)
C4	0.0188 (6)	0.0226 (7)	0.0197 (7)	−0.0045 (5)	−0.0018 (5)	−0.0098 (5)
C5	0.0164 (6)	0.0193 (7)	0.0231 (7)	−0.0027 (5)	−0.0042 (5)	−0.0088 (5)
C6	0.0179 (6)	0.0138 (6)	0.0209 (6)	−0.0041 (5)	−0.0058 (5)	−0.0061 (5)
C7	0.0192 (6)	0.0141 (6)	0.0215 (7)	−0.0053 (5)	−0.0060 (5)	−0.0056 (5)
C8	0.0214 (6)	0.0199 (7)	0.0259 (7)	−0.0036 (5)	−0.0085 (5)	−0.0061 (6)
C9	0.0285 (7)	0.0195 (7)	0.0281 (8)	−0.0039 (6)	−0.0144 (6)	−0.0036 (6)
C10	0.0331 (7)	0.0169 (7)	0.0187 (7)	−0.0096 (6)	−0.0100 (6)	−0.0017 (5)
C11	0.0239 (6)	0.0164 (6)	0.0195 (6)	−0.0085 (5)	−0.0045 (5)	−0.0047 (5)
C12	0.0201 (6)	0.0131 (6)	0.0209 (6)	−0.0064 (5)	−0.0064 (5)	−0.0048 (5)
C13	0.0160 (6)	0.0164 (6)	0.0175 (6)	−0.0058 (5)	−0.0034 (5)	−0.0057 (5)
C14	0.0200 (6)	0.0165 (6)	0.0152 (6)	−0.0047 (5)	−0.0028 (5)	−0.0047 (5)
C15	0.0210 (6)	0.0214 (7)	0.0208 (7)	−0.0051 (5)	−0.0039 (5)	−0.0056 (5)
C16	0.0228 (7)	0.0272 (8)	0.0287 (8)	−0.0016 (6)	−0.0022 (6)	−0.0102 (6)
C17	0.0333 (8)	0.0233 (8)	0.0383 (9)	0.0001 (6)	−0.0033 (7)	−0.0168 (7)
C18	0.0343 (8)	0.0215 (8)	0.0348 (9)	−0.0079 (6)	−0.0062 (7)	−0.0131 (6)
C19	0.0239 (7)	0.0176 (7)	0.0207 (7)	−0.0060 (5)	−0.0043 (5)	−0.0061 (5)
C20	0.0251 (7)	0.0140 (6)	0.0236 (7)	−0.0086 (5)	−0.0049 (5)	−0.0064 (5)
C21	0.0290 (7)	0.0180 (7)	0.0205 (7)	−0.0113 (6)	−0.0078 (5)	−0.0036 (5)
C22	0.0279 (7)	0.0198 (7)	0.0191 (7)	−0.0127 (6)	−0.0020 (5)	−0.0059 (5)
Cl1A	0.03125 (19)	0.0573 (3)	0.01955 (18)	−0.02149 (19)	−0.00780 (14)	−0.00025 (17)
Cl2A	0.0673 (3)	0.0322 (2)	0.0268 (2)	0.0014 (2)	−0.0264 (2)	−0.01023 (17)
O1A	0.0177 (4)	0.0138 (5)	0.0242 (5)	−0.0014 (4)	−0.0060 (4)	−0.0075 (4)
C1A	0.0158 (6)	0.0128 (6)	0.0202 (6)	−0.0029 (5)	−0.0052 (5)	−0.0055 (5)
C2A	0.0175 (6)	0.0183 (6)	0.0211 (7)	−0.0053 (5)	−0.0067 (5)	−0.0048 (5)
C3A	0.0238 (7)	0.0246 (7)	0.0182 (7)	−0.0100 (6)	−0.0067 (5)	−0.0026 (5)
C4A	0.0197 (6)	0.0255 (7)	0.0236 (7)	−0.0098 (6)	−0.0026 (5)	−0.0042 (6)
C5A	0.0167 (6)	0.0193 (7)	0.0291 (7)	−0.0060 (5)	−0.0076 (5)	−0.0055 (6)
C6A	0.0189 (6)	0.0130 (6)	0.0244 (7)	−0.0033 (5)	−0.0091 (5)	−0.0061 (5)
C7A	0.0224 (6)	0.0124 (6)	0.0262 (7)	−0.0022 (5)	−0.0123 (5)	−0.0058 (5)
C8A	0.0278 (7)	0.0204 (7)	0.0374 (9)	−0.0027 (6)	−0.0198 (6)	−0.0073 (6)
C9A	0.0416 (9)	0.0212 (7)	0.0394 (9)	0.0005 (6)	−0.0295 (8)	−0.0088 (7)
C10A	0.0446 (9)	0.0183 (7)	0.0250 (7)	0.0008 (6)	−0.0199 (7)	−0.0079 (6)
C11A	0.0312 (7)	0.0175 (7)	0.0231 (7)	0.0004 (6)	−0.0118 (6)	−0.0086 (6)
C12A	0.0232 (6)	0.0125 (6)	0.0221 (7)	−0.0007 (5)	−0.0106 (5)	−0.0073 (5)
C13A	0.0164 (6)	0.0142 (6)	0.0176 (6)	−0.0014 (5)	−0.0056 (5)	−0.0058 (5)
C14A	0.0180 (6)	0.0169 (6)	0.0138 (6)	−0.0047 (5)	−0.0038 (5)	−0.0040 (5)
C15A	0.0189 (6)	0.0185 (7)	0.0206 (7)	−0.0027 (5)	−0.0053 (5)	−0.0064 (5)
C16A	0.0176 (6)	0.0275 (8)	0.0260 (7)	−0.0066 (6)	−0.0041 (5)	−0.0064 (6)
C17A	0.0237 (7)	0.0242 (8)	0.0319 (8)	−0.0122 (6)	−0.0046 (6)	−0.0044 (6)
C18A	0.0238 (7)	0.0172 (7)	0.0281 (7)	−0.0067 (5)	−0.0059 (6)	−0.0041 (6)
C19A	0.0184 (6)	0.0175 (6)	0.0159 (6)	−0.0044 (5)	−0.0043 (5)	−0.0046 (5)
C20A	0.0180 (6)	0.0119 (6)	0.0201 (6)	−0.0032 (5)	−0.0047 (5)	−0.0061 (5)
C21A	0.0219 (6)	0.0147 (6)	0.0185 (6)	−0.0031 (5)	−0.0074 (5)	−0.0042 (5)
C22A	0.0214 (6)	0.0162 (6)	0.0161 (6)	−0.0045 (5)	−0.0033 (5)	−0.0049 (5)
N1B	0.0200 (5)	0.0185 (6)	0.0241 (6)	−0.0034 (4)	−0.0066 (5)	−0.0084 (5)
C1B	0.0227 (7)	0.0299 (8)	0.0300 (8)	−0.0084 (6)	−0.0037 (6)	−0.0122 (6)
C2B	0.0356 (8)	0.0369 (9)	0.0271 (8)	−0.0120 (7)	−0.0035 (7)	−0.0101 (7)
C3B	0.0253 (7)	0.0212 (7)	0.0257 (7)	−0.0033 (6)	−0.0096 (6)	−0.0079 (6)
C4B	0.0301 (8)	0.0315 (8)	0.0323 (8)	−0.0045 (6)	−0.0114 (6)	−0.0161 (7)
C5B	0.0242 (7)	0.0189 (7)	0.0280 (7)	−0.0022 (5)	−0.0090 (6)	−0.0078 (6)
C6B	0.0223 (7)	0.0279 (8)	0.0356 (9)	−0.0011 (6)	−0.0078 (6)	−0.0110 (7)
N1C	0.0219 (12)	0.0267 (8)	0.0237 (19)	−0.0050 (8)	−0.0074 (13)	−0.0075 (9)
C1C	0.035 (2)	0.038 (3)	0.026 (2)	−0.009 (2)	−0.0104 (18)	−0.0003 (19)
C2C	0.034 (4)	0.055 (5)	0.038 (3)	−0.019 (3)	−0.008 (3)	0.005 (3)
C3C	0.0278 (17)	0.031 (2)	0.032 (2)	−0.0087 (15)	−0.0125 (15)	−0.0090 (15)
C4C	0.032 (3)	0.035 (5)	0.036 (4)	−0.007 (3)	−0.014 (3)	−0.015 (4)
C5C	0.0206 (15)	0.029 (2)	0.0225 (19)	−0.0028 (13)	−0.0084 (13)	−0.0057 (14)
C6C	0.034 (3)	0.035 (3)	0.023 (4)	−0.004 (3)	−0.008 (3)	−0.007 (3)
N1CA	0.0219 (12)	0.0267 (8)	0.0237 (19)	−0.0050 (8)	−0.0074 (13)	−0.0075 (9)
C1CA	0.0298 (17)	0.0235 (18)	0.046 (2)	−0.0022 (13)	−0.0211 (15)	−0.0059 (14)
C2CA	0.041 (3)	0.034 (2)	0.041 (3)	−0.017 (2)	−0.011 (3)	−0.0003 (17)
C3CA	0.0290 (13)	0.0302 (16)	0.0298 (15)	−0.0045 (11)	−0.0131 (11)	−0.0103 (12)
C4CA	0.029 (2)	0.025 (3)	0.039 (4)	−0.0059 (17)	−0.015 (2)	−0.005 (2)
C5CA	0.0266 (14)	0.046 (2)	0.0378 (17)	−0.0115 (13)	−0.0037 (12)	−0.0185 (14)
C6CA	0.039 (3)	0.060 (5)	0.041 (5)	−0.013 (3)	−0.005 (4)	−0.021 (4)
N1D	0.0213 (10)	0.0215 (14)	0.030 (3)	−0.0069 (8)	−0.0059 (19)	−0.009 (2)
C1D	0.0354 (18)	0.0319 (19)	0.041 (2)	0.0001 (15)	−0.0150 (16)	−0.0126 (16)
C2D	0.083 (4)	0.046 (3)	0.040 (3)	−0.020 (3)	−0.021 (3)	−0.008 (2)
C3D	0.061 (3)	0.036 (2)	0.029 (2)	−0.028 (2)	−0.001 (2)	−0.014 (2)
C4D	0.075 (3)	0.048 (3)	0.038 (2)	−0.033 (2)	0.001 (2)	−0.0221 (18)
C5D	0.018 (4)	0.058 (6)	0.112 (7)	−0.004 (4)	−0.012 (4)	−0.060 (5)
C6D	0.0235 (15)	0.0343 (19)	0.060 (2)	−0.0085 (14)	−0.0069 (15)	−0.0190 (17)
N1DA	0.0213 (10)	0.0215 (14)	0.030 (3)	−0.0069 (8)	−0.0059 (19)	−0.009 (2)
C1DA	0.0350 (18)	0.0208 (18)	0.033 (2)	−0.0121 (14)	−0.0138 (18)	−0.0029 (16)
C2DA	0.049 (2)	0.0192 (17)	0.048 (2)	−0.0123 (14)	−0.0269 (17)	0.0003 (14)
C3DA	0.0309 (16)	0.0271 (18)	0.039 (2)	−0.0080 (14)	−0.0002 (14)	−0.0149 (17)
C4DA	0.061 (3)	0.045 (3)	0.028 (2)	−0.024 (2)	0.004 (2)	−0.016 (2)
C5DA	0.034 (5)	0.019 (3)	0.026 (2)	−0.013 (3)	−0.012 (2)	0.000 (2)
C6DA	0.072 (3)	0.054 (3)	0.165 (7)	0.014 (3)	−0.083 (4)	−0.047 (4)

Geometric parameters (Å, º)

Cl1—C3	1.7427 (14)	C3B—H3B1	0.9900
Cl2—C10	1.7502 (15)	C3B—H3B2	0.9900
O1—C13	1.4229 (15)	C4B—H4B1	0.9800
O1—H1	0.8400	C4B—H4B2	0.9800
C1—C2	1.3804 (19)	C4B—H4B3	0.9800
C1—C6	1.4009 (18)	C5B—C6B	1.516 (2)
C1—C13	1.5282 (18)	C5B—H5B1	0.9900
C2—C3	1.3951 (19)	C5B—H5B2	0.9900
C2—H2	0.9500	C6B—H6B1	0.9800
C3—C4	1.3945 (19)	C6B—H6B2	0.9800
C4—C5	1.391 (2)	C6B—H6B3	0.9800
C4—H4	0.9500	N1C—C5C	1.466 (8)
C5—C6	1.3893 (18)	N1C—C1C	1.471 (8)
C5—H5	0.9500	N1C—C3C	1.473 (8)
C6—C7	1.4709 (19)	C1C—C2C	1.515 (8)
C7—C8	1.3906 (19)	C1C—H1C1	0.9900
C7—C12	1.4017 (18)	C1C—H1C2	0.9900
C8—C9	1.394 (2)	C2C—H2C1	0.9800
C8—H8	0.9500	C2C—H2C2	0.9800
C9—C10	1.387 (2)	C2C—H2C3	0.9800
C9—H9	0.9500	C3C—C4C	1.516 (9)
C10—C11	1.392 (2)	C3C—H3C1	0.9900
C11—C12	1.3782 (19)	C3C—H3C2	0.9900
C11—H11	0.9500	C4C—H4C1	0.9800
C12—C13	1.5296 (18)	C4C—H4C2	0.9800
C13—C14	1.5369 (19)	C4C—H4C3	0.9800
C14—C15	1.3945 (19)	C5C—C6C	1.521 (7)
C14—C19	1.4109 (19)	C5C—H5C1	0.9900
C15—C16	1.388 (2)	C5C—H5C2	0.9900
C15—H15	0.9500	C6C—H6C1	0.9800
C16—C17	1.380 (2)	C6C—H6C2	0.9800
C16—H16	0.9500	C6C—H6C3	0.9800
C17—C18	1.384 (2)	N1CA—C1CA	1.467 (6)
C17—H17	0.9500	N1CA—C5CA	1.470 (7)
C18—C19	1.398 (2)	N1CA—C3CA	1.470 (6)
C18—H18	0.9500	C1CA—C2CA	1.516 (5)
C19—C20	1.4935 (19)	C1CA—H1C3	0.9900
C20—C21	1.396 (2)	C1CA—H1C4	0.9900
C20—C22^i	1.398 (2)	C2CA—H2C4	0.9800
C21—C22	1.387 (2)	C2CA—H2C5	0.9800
C21—H21	0.9500	C2CA—H2C6	0.9800
C22—C20^i	1.398 (2)	C3CA—C4CA	1.519 (7)
C22—H22	0.9500	C3CA—H3C3	0.9900
Cl1A—C3A	1.7383 (15)	C3CA—H3C4	0.9900
Cl2A—C10A	1.7408 (16)	C4CA—H4C4	0.9800
O1A—C13A	1.4243 (15)	C4CA—H4C5	0.9800
O1A—H1A	0.8400	C4CA—H4C6	0.9800
C1A—C2A	1.3777 (19)	C5CA—C6CA	1.522 (7)
C1A—C6A	1.4022 (17)	C5CA—H5C3	0.9900
C1A—C13A	1.5252 (18)	C5CA—H5C4	0.9900
C2A—C3A	1.3905 (19)	C6CA—H6C4	0.9800
C2A—H2A	0.9500	C6CA—H6C5	0.9800
C3A—C4A	1.395 (2)	C6CA—H6C6	0.9800
C4A—C5A	1.391 (2)	N1D—C1D	1.452 (6)
C4A—H4A	0.9500	N1D—C3D	1.472 (6)
C5A—C6A	1.3877 (19)	N1D—C5D	1.478 (7)
C5A—H5A	0.9500	C1D—C2D	1.508 (5)
C6A—C7A	1.4693 (19)	C1D—H1D1	0.9900
C7A—C8A	1.3937 (19)	C1D—H1D2	0.9900
C7A—C12A	1.3983 (19)	C2D—H2D1	0.9800
C8A—C9A	1.390 (2)	C2D—H2D2	0.9800
C8A—H8A	0.9500	C2D—H2D3	0.9800
C9A—C10A	1.382 (2)	C3D—C4D	1.520 (5)
C9A—H9A	0.9500	C3D—H3D1	0.9900
C10A—C11A	1.395 (2)	C3D—H3D2	0.9900
C11A—C12A	1.378 (2)	C4D—H4D1	0.9800
C11A—H11A	0.9500	C4D—H4D2	0.9800
C12A—C13A	1.5311 (18)	C4D—H4D3	0.9800
C13A—C14A	1.5308 (18)	C5D—C6D	1.579 (7)
C14A—C15A	1.3978 (18)	C5D—H5D1	0.9900
C14A—C19A	1.4100 (19)	C5D—H5D2	0.9900
C15A—C16A	1.389 (2)	C6D—H6D1	0.9800
C15A—H15A	0.9500	C6D—H6D2	0.9800
C16A—C17A	1.380 (2)	C6D—H6D3	0.9800
C16A—H16A	0.9500	N1DA—C1DA	1.469 (6)
C17A—C18A	1.391 (2)	N1DA—C3DA	1.471 (6)
C17A—H17A	0.9500	N1DA—C5DA	1.484 (7)
C18A—C19A	1.3964 (19)	C1DA—C2DA	1.529 (4)
C18A—H18A	0.9500	C1DA—H1D3	0.9900
C19A—C20A	1.4979 (18)	C1DA—H1D4	0.9900
C20A—C22A^ii	1.3956 (19)	C2DA—H2D4	0.9800
C20A—C21A	1.3966 (19)	C2DA—H2D5	0.9800
C21A—C22A	1.3891 (19)	C2DA—H2D6	0.9800
C21A—H21A	0.9500	C3DA—C4DA	1.521 (5)
C22A—C20A^ii	1.3956 (19)	C3DA—H3D3	0.9900
C22A—H22A	0.9500	C3DA—H3D4	0.9900
N1B—C1B	1.4714 (18)	C4DA—H4D4	0.9800
N1B—C5B	1.4754 (18)	C4DA—H4D5	0.9800
N1B—C3B	1.4809 (19)	C4DA—H4D6	0.9800
C1B—C2B	1.519 (2)	C5DA—C6DA	1.589 (7)
C1B—H1B1	0.9900	C5DA—H5D3	0.9900
C1B—H1B2	0.9900	C5DA—H5D4	0.9900
C2B—H2B1	0.9800	C6DA—H6D4	0.9800
C2B—H2B2	0.9800	C6DA—H6D5	0.9800
C2B—H2B3	0.9800	C6DA—H6D6	0.9800
C3B—C4B	1.527 (2)
C13—O1—H1	109.5	N1B—C5B—H5B1	108.9
C2—C1—C6	121.32 (12)	C6B—C5B—H5B1	108.9
C2—C1—C13	127.78 (12)	N1B—C5B—H5B2	108.9
C6—C1—C13	110.87 (11)	C6B—C5B—H5B2	108.9
C1—C2—C3	117.59 (12)	H5B1—C5B—H5B2	107.7
C1—C2—H2	121.2	C5B—C6B—H6B1	109.5
C3—C2—H2	121.2	C5B—C6B—H6B2	109.5
C4—C3—C2	122.09 (13)	H6B1—C6B—H6B2	109.5
C4—C3—Cl1	119.22 (11)	C5B—C6B—H6B3	109.5
C2—C3—Cl1	118.69 (11)	H6B1—C6B—H6B3	109.5
C5—C4—C3	119.43 (12)	H6B2—C6B—H6B3	109.5
C5—C4—H4	120.3	C5C—N1C—C1C	109.4 (7)
C3—C4—H4	120.3	C5C—N1C—C3C	110.0 (7)
C6—C5—C4	119.23 (12)	C1C—N1C—C3C	110.4 (7)
C6—C5—H5	120.4	N1C—C1C—C2C	113.1 (7)
C4—C5—H5	120.4	N1C—C1C—H1C1	109.0
C5—C6—C1	120.30 (13)	C2C—C1C—H1C1	109.0
C5—C6—C7	130.96 (12)	N1C—C1C—H1C2	109.0
C1—C6—C7	108.71 (11)	C2C—C1C—H1C2	109.0
C8—C7—C12	120.11 (13)	H1C1—C1C—H1C2	107.8
C8—C7—C6	131.60 (13)	C1C—C2C—H2C1	109.5
C12—C7—C6	108.27 (12)	C1C—C2C—H2C2	109.5
C7—C8—C9	119.29 (13)	H2C1—C2C—H2C2	109.5
C7—C8—H8	120.4	C1C—C2C—H2C3	109.5
C9—C8—H8	120.4	H2C1—C2C—H2C3	109.5
C10—C9—C8	119.12 (13)	H2C2—C2C—H2C3	109.5
C10—C9—H9	120.4	N1C—C3C—C4C	113.3 (8)
C8—C9—H9	120.4	N1C—C3C—H3C1	108.9
C9—C10—C11	122.68 (13)	C4C—C3C—H3C1	108.9
C9—C10—Cl2	118.86 (11)	N1C—C3C—H3C2	108.9
C11—C10—Cl2	118.44 (11)	C4C—C3C—H3C2	108.9
C12—C11—C10	117.41 (13)	H3C1—C3C—H3C2	107.7
C12—C11—H11	121.3	C3C—C4C—H4C1	109.5
C10—C11—H11	121.3	C3C—C4C—H4C2	109.5
C11—C12—C7	121.39 (13)	H4C1—C4C—H4C2	109.5
C11—C12—C13	127.54 (12)	C3C—C4C—H4C3	109.5
C7—C12—C13	111.07 (12)	H4C1—C4C—H4C3	109.5
O1—C13—C1	111.11 (10)	H4C2—C4C—H4C3	109.5
O1—C13—C12	111.35 (11)	N1C—C5C—C6C	112.6 (7)
C1—C13—C12	101.02 (10)	N1C—C5C—H5C1	109.1
O1—C13—C14	107.02 (10)	C6C—C5C—H5C1	109.1
C1—C13—C14	114.40 (11)	N1C—C5C—H5C2	109.1
C12—C13—C14	111.99 (11)	C6C—C5C—H5C2	109.1
C15—C14—C19	118.90 (13)	H5C1—C5C—H5C2	107.8
C15—C14—C13	118.26 (12)	C5C—C6C—H6C1	109.5
C19—C14—C13	122.80 (12)	C5C—C6C—H6C2	109.5
C16—C15—C14	121.50 (14)	H6C1—C6C—H6C2	109.5
C16—C15—H15	119.2	C5C—C6C—H6C3	109.5
C14—C15—H15	119.2	H6C1—C6C—H6C3	109.5
C17—C16—C15	119.80 (14)	H6C2—C6C—H6C3	109.5
C17—C16—H16	120.1	C1CA—N1CA—C5CA	110.5 (6)
C15—C16—H16	120.1	C1CA—N1CA—C3CA	110.3 (5)
C16—C17—C18	119.45 (15)	C5CA—N1CA—C3CA	110.3 (5)
C16—C17—H17	120.3	N1CA—C1CA—C2CA	113.7 (5)
C18—C17—H17	120.3	N1CA—C1CA—H1C3	108.8
C17—C18—C19	121.92 (15)	C2CA—C1CA—H1C3	108.8
C17—C18—H18	119.0	N1CA—C1CA—H1C4	108.8
C19—C18—H18	119.0	C2CA—C1CA—H1C4	108.8
C18—C19—C14	118.42 (13)	H1C3—C1CA—H1C4	107.7
C18—C19—C20	117.00 (13)	C1CA—C2CA—H2C4	109.5
C14—C19—C20	124.57 (12)	C1CA—C2CA—H2C5	109.5
C21—C20—C22^i	118.20 (13)	H2C4—C2CA—H2C5	109.5
C21—C20—C19	121.51 (13)	C1CA—C2CA—H2C6	109.5
C22^i—C20—C19	120.16 (13)	H2C4—C2CA—H2C6	109.5
C22—C21—C20	120.84 (13)	H2C5—C2CA—H2C6	109.5
C22—C21—H21	119.6	N1CA—C3CA—C4CA	113.5 (6)
C20—C21—H21	119.6	N1CA—C3CA—H3C3	108.9
C21—C22—C20^i	120.95 (13)	C4CA—C3CA—H3C3	108.9
C21—C22—H22	119.5	N1CA—C3CA—H3C4	108.9
C20^i—C22—H22	119.5	C4CA—C3CA—H3C4	108.9
C13A—O1A—H1A	109.5	H3C3—C3CA—H3C4	107.7
C2A—C1A—C6A	121.37 (12)	C3CA—C4CA—H4C4	109.5
C2A—C1A—C13A	127.42 (11)	C3CA—C4CA—H4C5	109.5
C6A—C1A—C13A	111.20 (12)	H4C4—C4CA—H4C5	109.5
C1A—C2A—C3A	117.54 (12)	C3CA—C4CA—H4C6	109.5
C1A—C2A—H2A	121.2	H4C4—C4CA—H4C6	109.5
C3A—C2A—H2A	121.2	H4C5—C4CA—H4C6	109.5
C2A—C3A—C4A	122.28 (13)	N1CA—C5CA—C6CA	112.3 (6)
C2A—C3A—Cl1A	118.45 (11)	N1CA—C5CA—H5C3	109.1
C4A—C3A—Cl1A	119.26 (11)	C6CA—C5CA—H5C3	109.1
C5A—C4A—C3A	119.30 (13)	N1CA—C5CA—H5C4	109.1
C5A—C4A—H4A	120.4	C6CA—C5CA—H5C4	109.1
C3A—C4A—H4A	120.4	H5C3—C5CA—H5C4	107.9
C6A—C5A—C4A	119.19 (12)	C5CA—C6CA—H6C4	109.5
C6A—C5A—H5A	120.4	C5CA—C6CA—H6C5	109.5
C4A—C5A—H5A	120.4	H6C4—C6CA—H6C5	109.5
C5A—C6A—C1A	120.27 (13)	C5CA—C6CA—H6C6	109.5
C5A—C6A—C7A	131.30 (12)	H6C4—C6CA—H6C6	109.5
C1A—C6A—C7A	108.37 (12)	H6C5—C6CA—H6C6	109.5
C8A—C7A—C12A	120.06 (14)	C1D—N1D—C3D	111.1 (5)
C8A—C7A—C6A	131.51 (14)	C1D—N1D—C5D	108.6 (6)
C12A—C7A—C6A	108.43 (11)	C3D—N1D—C5D	114.6 (5)
C9A—C8A—C7A	118.70 (15)	N1D—C1D—C2D	114.4 (4)
C9A—C8A—H8A	120.7	N1D—C1D—H1D1	108.7
C7A—C8A—H8A	120.7	C2D—C1D—H1D1	108.7
C10A—C9A—C8A	120.05 (14)	N1D—C1D—H1D2	108.7
C10A—C9A—H9A	120.0	C2D—C1D—H1D2	108.7
C8A—C9A—H9A	120.0	H1D1—C1D—H1D2	107.6
C9A—C10A—C11A	122.21 (15)	C1D—C2D—H2D1	109.5
C9A—C10A—Cl2A	118.90 (12)	C1D—C2D—H2D2	109.5
C11A—C10A—Cl2A	118.87 (13)	H2D1—C2D—H2D2	109.5
C12A—C11A—C10A	117.19 (15)	C1D—C2D—H2D3	109.5
C12A—C11A—H11A	121.4	H2D1—C2D—H2D3	109.5
C10A—C11A—H11A	121.4	H2D2—C2D—H2D3	109.5
C11A—C12A—C7A	121.76 (13)	N1D—C3D—C4D	117.0 (5)
C11A—C12A—C13A	127.11 (13)	N1D—C3D—H3D1	108.1
C7A—C12A—C13A	111.13 (12)	C4D—C3D—H3D1	108.1
O1A—C13A—C1A	111.32 (10)	N1D—C3D—H3D2	108.1
O1A—C13A—C14A	107.22 (10)	C4D—C3D—H3D2	108.1
C1A—C13A—C14A	114.25 (11)	H3D1—C3D—H3D2	107.3
O1A—C13A—C12A	110.73 (10)	C3D—C4D—H4D1	109.5
C1A—C13A—C12A	100.74 (10)	C3D—C4D—H4D2	109.5
C14A—C13A—C12A	112.58 (11)	H4D1—C4D—H4D2	109.5
C15A—C14A—C19A	118.83 (12)	C3D—C4D—H4D3	109.5
C15A—C14A—C13A	118.53 (12)	H4D1—C4D—H4D3	109.5
C19A—C14A—C13A	122.59 (11)	H4D2—C4D—H4D3	109.5
C16A—C15A—C14A	121.32 (13)	N1D—C5D—C6D	121.3 (7)
C16A—C15A—H15A	119.3	N1D—C5D—H5D1	107.0
C14A—C15A—H15A	119.3	C6D—C5D—H5D1	107.0
C17A—C16A—C15A	119.96 (13)	N1D—C5D—H5D2	107.0
C17A—C16A—H16A	120.0	C6D—C5D—H5D2	107.0
C15A—C16A—H16A	120.0	H5D1—C5D—H5D2	106.7
C16A—C17A—C18A	119.45 (13)	C5D—C6D—H6D1	109.5
C16A—C17A—H17A	120.3	C5D—C6D—H6D2	109.5
C18A—C17A—H17A	120.3	H6D1—C6D—H6D2	109.5
C17A—C18A—C19A	121.57 (14)	C5D—C6D—H6D3	109.5
C17A—C18A—H18A	119.2	H6D1—C6D—H6D3	109.5
C19A—C18A—H18A	119.2	H6D2—C6D—H6D3	109.5
C18A—C19A—C14A	118.79 (12)	C1DA—N1DA—C3DA	110.3 (5)
C18A—C19A—C20A	116.71 (12)	C1DA—N1DA—C5DA	115.5 (5)
C14A—C19A—C20A	124.50 (12)	C3DA—N1DA—C5DA	110.9 (5)
C22A^ii—C20A—C21A	118.27 (12)	N1DA—C1DA—C2DA	117.3 (4)
C22A^ii—C20A—C19A	120.83 (12)	N1DA—C1DA—H1D3	108.0
C21A—C20A—C19A	120.78 (12)	C2DA—C1DA—H1D3	108.0
C22A—C21A—C20A	120.81 (13)	N1DA—C1DA—H1D4	108.0
C22A—C21A—H21A	119.6	C2DA—C1DA—H1D4	108.0
C20A—C21A—H21A	119.6	H1D3—C1DA—H1D4	107.2
C21A—C22A—C20A^ii	120.92 (12)	C1DA—C2DA—H2D4	109.5
C21A—C22A—H22A	119.5	C1DA—C2DA—H2D5	109.5
C20A^ii—C22A—H22A	119.5	H2D4—C2DA—H2D5	109.5
C1B—N1B—C5B	111.33 (12)	C1DA—C2DA—H2D6	109.5
C1B—N1B—C3B	110.96 (11)	H2D4—C2DA—H2D6	109.5
C5B—N1B—C3B	113.05 (11)	H2D5—C2DA—H2D6	109.5
N1B—C1B—C2B	113.88 (13)	N1DA—C3DA—C4DA	113.9 (4)
N1B—C1B—H1B1	108.8	N1DA—C3DA—H3D3	108.8
C2B—C1B—H1B1	108.8	C4DA—C3DA—H3D3	108.8
N1B—C1B—H1B2	108.8	N1DA—C3DA—H3D4	108.8
C2B—C1B—H1B2	108.8	C4DA—C3DA—H3D4	108.8
H1B1—C1B—H1B2	107.7	H3D3—C3DA—H3D4	107.7
C1B—C2B—H2B1	109.5	C3DA—C4DA—H4D4	109.5
C1B—C2B—H2B2	109.5	C3DA—C4DA—H4D5	109.5
H2B1—C2B—H2B2	109.5	H4D4—C4DA—H4D5	109.5
C1B—C2B—H2B3	109.5	C3DA—C4DA—H4D6	109.5
H2B1—C2B—H2B3	109.5	H4D4—C4DA—H4D6	109.5
H2B2—C2B—H2B3	109.5	H4D5—C4DA—H4D6	109.5
N1B—C3B—C4B	116.88 (13)	N1DA—C5DA—C6DA	118.7 (5)
N1B—C3B—H3B1	108.1	N1DA—C5DA—H5D3	107.6
C4B—C3B—H3B1	108.1	C6DA—C5DA—H5D3	107.6
N1B—C3B—H3B2	108.1	N1DA—C5DA—H5D4	107.6
C4B—C3B—H3B2	108.1	C6DA—C5DA—H5D4	107.6
H3B1—C3B—H3B2	107.3	H5D3—C5DA—H5D4	107.1
C3B—C4B—H4B1	109.5	C5DA—C6DA—H6D4	109.5
C3B—C4B—H4B2	109.5	C5DA—C6DA—H6D5	109.5
H4B1—C4B—H4B2	109.5	H6D4—C6DA—H6D5	109.5
C3B—C4B—H4B3	109.5	C5DA—C6DA—H6D6	109.5
H4B1—C4B—H4B3	109.5	H6D4—C6DA—H6D6	109.5
H4B2—C4B—H4B3	109.5	H6D5—C6DA—H6D6	109.5
N1B—C5B—C6B	113.51 (12)
C6—C1—C2—C3	0.5 (2)	C5A—C6A—C7A—C12A	−175.28 (14)
C13—C1—C2—C3	178.35 (13)	C1A—C6A—C7A—C12A	2.01 (15)
C1—C2—C3—C4	1.1 (2)	C12A—C7A—C8A—C9A	0.9 (2)
C1—C2—C3—Cl1	−179.17 (10)	C6A—C7A—C8A—C9A	−178.38 (14)
C2—C3—C4—C5	−1.4 (2)	C7A—C8A—C9A—C10A	0.9 (2)
Cl1—C3—C4—C5	178.80 (11)	C8A—C9A—C10A—C11A	−1.7 (2)
C3—C4—C5—C6	0.2 (2)	C8A—C9A—C10A—Cl2A	176.99 (12)
C4—C5—C6—C1	1.4 (2)	C9A—C10A—C11A—C12A	0.6 (2)
C4—C5—C6—C7	179.40 (13)	Cl2A—C10A—C11A—C12A	−178.09 (11)
C2—C1—C6—C5	−1.8 (2)	C10A—C11A—C12A—C7A	1.3 (2)
C13—C1—C6—C5	−179.92 (12)	C10A—C11A—C12A—C13A	−177.59 (13)
C2—C1—C6—C7	179.81 (12)	C8A—C7A—C12A—C11A	−2.0 (2)
C13—C1—C6—C7	1.66 (15)	C6A—C7A—C12A—C11A	177.39 (12)
C5—C6—C7—C8	0.0 (3)	C8A—C7A—C12A—C13A	177.00 (12)
C1—C6—C7—C8	178.18 (14)	C6A—C7A—C12A—C13A	−3.57 (15)
C5—C6—C7—C12	−178.43 (14)	C2A—C1A—C13A—O1A	−64.61 (17)
C1—C6—C7—C12	−0.24 (15)	C6A—C1A—C13A—O1A	115.17 (12)
C12—C7—C8—C9	0.3 (2)	C2A—C1A—C13A—C14A	57.01 (18)
C6—C7—C8—C9	−177.96 (14)	C6A—C1A—C13A—C14A	−123.21 (12)
C7—C8—C9—C10	−0.3 (2)	C2A—C1A—C13A—C12A	177.95 (13)
C8—C9—C10—C11	−0.3 (2)	C6A—C1A—C13A—C12A	−2.27 (14)
C8—C9—C10—Cl2	177.89 (11)	C11A—C12A—C13A—O1A	64.65 (17)
C9—C10—C11—C12	0.7 (2)	C7A—C12A—C13A—O1A	−114.32 (12)
Cl2—C10—C11—C12	−177.43 (10)	C11A—C12A—C13A—C1A	−177.48 (13)
C10—C11—C12—C7	−0.7 (2)	C7A—C12A—C13A—C1A	3.54 (14)
C10—C11—C12—C13	179.42 (12)	C11A—C12A—C13A—C14A	−55.37 (18)
C8—C7—C12—C11	0.2 (2)	C7A—C12A—C13A—C14A	125.66 (12)
C6—C7—C12—C11	178.82 (12)	O1A—C13A—C14A—C15A	5.45 (16)
C8—C7—C12—C13	−179.90 (12)	C1A—C13A—C14A—C15A	−118.40 (13)
C6—C7—C12—C13	−1.27 (15)	C12A—C13A—C14A—C15A	127.48 (13)
C2—C1—C13—O1	−62.04 (17)	O1A—C13A—C14A—C19A	−171.97 (12)
C6—C1—C13—O1	115.96 (12)	C1A—C13A—C14A—C19A	64.18 (16)
C2—C1—C13—C12	179.74 (13)	C12A—C13A—C14A—C19A	−49.94 (17)
C6—C1—C13—C12	−2.26 (14)	C19A—C14A—C15A—C16A	2.5 (2)
C2—C1—C13—C14	59.26 (18)	C13A—C14A—C15A—C16A	−175.04 (13)
C6—C1—C13—C14	−122.74 (12)	C14A—C15A—C16A—C17A	−0.1 (2)
C11—C12—C13—O1	63.97 (17)	C15A—C16A—C17A—C18A	−1.4 (2)
C7—C12—C13—O1	−115.93 (12)	C16A—C17A—C18A—C19A	0.6 (2)
C11—C12—C13—C1	−177.99 (13)	C17A—C18A—C19A—C14A	1.8 (2)
C7—C12—C13—C1	2.11 (14)	C17A—C18A—C19A—C20A	−177.53 (14)
C11—C12—C13—C14	−55.82 (17)	C15A—C14A—C19A—C18A	−3.2 (2)
C7—C12—C13—C14	124.28 (12)	C13A—C14A—C19A—C18A	174.17 (13)
O1—C13—C14—C15	6.18 (16)	C15A—C14A—C19A—C20A	176.00 (13)
C1—C13—C14—C15	−117.35 (13)	C13A—C14A—C19A—C20A	−6.6 (2)
C12—C13—C14—C15	128.47 (13)	C18A—C19A—C20A—C22A^ii	−77.30 (17)
O1—C13—C14—C19	−171.45 (12)	C14A—C19A—C20A—C22A^ii	103.44 (16)
C1—C13—C14—C19	65.02 (17)	C18A—C19A—C20A—C21A	98.52 (16)
C12—C13—C14—C19	−49.16 (17)	C14A—C19A—C20A—C21A	−80.73 (18)
C19—C14—C15—C16	1.4 (2)	C22A^ii—C20A—C21A—C22A	−0.6 (2)
C13—C14—C15—C16	−176.30 (13)	C19A—C20A—C21A—C22A	−176.54 (13)
C14—C15—C16—C17	−0.6 (2)	C20A—C21A—C22A—C20A^ii	0.6 (2)
C15—C16—C17—C18	−0.2 (3)	C5B—N1B—C1B—C2B	62.98 (17)
C16—C17—C18—C19	0.1 (3)	C3B—N1B—C1B—C2B	−170.17 (13)
C17—C18—C19—C14	0.8 (2)	C1B—N1B—C3B—C4B	−71.11 (16)
C17—C18—C19—C20	179.49 (15)	C5B—N1B—C3B—C4B	54.78 (17)
C15—C14—C19—C18	−1.5 (2)	C1B—N1B—C5B—C6B	−177.19 (13)
C13—C14—C19—C18	176.09 (13)	C3B—N1B—C5B—C6B	57.12 (16)
C15—C14—C19—C20	179.91 (13)	C5C—N1C—C1C—C2C	−72.5 (10)
C13—C14—C19—C20	−2.5 (2)	C3C—N1C—C1C—C2C	166.3 (7)
C18—C19—C20—C21	102.54 (17)	C5C—N1C—C3C—C4C	174.3 (9)
C14—C19—C20—C21	−78.87 (19)	C1C—N1C—C3C—C4C	−64.8 (11)
C18—C19—C20—C22^i	−73.40 (18)	C1C—N1C—C5C—C6C	170.4 (8)
C14—C19—C20—C22^i	105.19 (17)	C3C—N1C—C5C—C6C	−68.2 (11)
C22^i—C20—C21—C22	−0.8 (2)	C5CA—N1CA—C1CA—C2CA	−161.8 (5)
C19—C20—C21—C22	−176.85 (13)	C3CA—N1CA—C1CA—C2CA	75.9 (8)
C20—C21—C22—C20^i	0.9 (2)	C1CA—N1CA—C3CA—C4CA	−164.3 (7)
C6A—C1A—C2A—C3A	1.4 (2)	C5CA—N1CA—C3CA—C4CA	73.4 (9)
C13A—C1A—C2A—C3A	−178.87 (13)	C1CA—N1CA—C5CA—C6CA	78.2 (8)
C1A—C2A—C3A—C4A	0.6 (2)	C3CA—N1CA—C5CA—C6CA	−159.6 (6)
C1A—C2A—C3A—Cl1A	−179.27 (11)	C3D—N1D—C1D—C2D	−171.4 (5)
C2A—C3A—C4A—C5A	−1.8 (2)	C5D—N1D—C1D—C2D	61.8 (7)
Cl1A—C3A—C4A—C5A	178.12 (11)	C1D—N1D—C3D—C4D	−69.0 (7)
C3A—C4A—C5A—C6A	0.9 (2)	C5D—N1D—C3D—C4D	54.4 (8)
C4A—C5A—C6A—C1A	1.0 (2)	C1D—N1D—C5D—C6D	−84.2 (9)
C4A—C5A—C6A—C7A	178.05 (14)	C3D—N1D—C5D—C6D	151.0 (7)
C2A—C1A—C6A—C5A	−2.2 (2)	C3DA—N1DA—C1DA—C2DA	72.0 (6)
C13A—C1A—C6A—C5A	177.97 (12)	C5DA—N1DA—C1DA—C2DA	−54.7 (7)
C2A—C1A—C6A—C7A	−179.86 (12)	C1DA—N1DA—C3DA—C4DA	171.1 (4)
C13A—C1A—C6A—C7A	0.34 (15)	C5DA—N1DA—C3DA—C4DA	−59.7 (6)
C5A—C6A—C7A—C8A	4.1 (3)	C1DA—N1DA—C5DA—C6DA	−147.3 (6)
C1A—C6A—C7A—C8A	−178.65 (15)	C3DA—N1DA—C5DA—C6DA	86.3 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1D^iii	0.84	1.95	2.781 (2)	171
O1—H1···N1DA^iii	0.84	1.91	2.731 (2)	164
O1A—H1A···N1B^iv	0.84	1.94	2.766 (2)	167
C4—H4···O1A^v	0.95	2.54	3.489 (2)	175
C4A—H4A···O1^vi	0.95	2.47	3.403 (2)	168
C9—H9···N1C^vii	0.95	2.54	3.459 (2)	163
C9—H9···N1CA^vii	0.95	2.60	3.519 (2)	162
C2DA—H2D6···Cl2A	0.98	2.90	3.819 (4)	157
C15—H15···O1	0.95	2.22	2.621 (2)	104
C15A—H15A···O1A	0.95	2.23	2.626 (2)	104

Symmetry codes: (iii) x, y, z−1; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z+1; (vi) −x+2, −y+1, −z; (vii) −x+1, −y+1, −z.