Crystal structure and supra­molecular features of a bis-urea-functionalized pillar[5]arene

The crystal structure and supra­molecular features are reported of a dimeric bis-urea-functionalized pillar[5]arene macrocycle, which functions as a receptor system to the DMF guest mol­ecule.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.157
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         20 Note

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        47% Check
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........     Please Check
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O13      0.110 Check
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C40A     --C45A     .       1.36 Ang.
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C50B     --C55B     .       1.36 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N2A      --H2A1     .     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     24.899 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.184 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.096 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         86 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         50 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        30% Note
PLAT410_ALERT_2_G Short Intra H...H Contact  H5       ..H46A     .       2.10 Ang.
                                                      x,y,z  =      1_555 Check
PLAT414_ALERT_2_G Short Intra D-H..H-X       H1A      ..H56C     .       2.06 Ang.
                                                      x,y,z  =      1_555 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        886 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  12 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
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
  11 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrystalClear 2.1 b46 (Rigaku, 2016); cell refinement: CrystalClear 2.1 b46; data reduction: CrystalClear 2.1 b46; program(s) used to solve structure: CrystalStructure 4.2 (Rigaku, 2017); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020).

Bis-urea derivative based on A1/A2-functionalized pillar[5]arene dimethylformamide monosolvate

Crystal data

C63H70N4O12·C3H7NO	F(000) = 2448
Mr = 1148.32	Dx = 1.227 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 14.7726 (9) Å	Cell parameters from 22911 reflections
b = 16.2952 (11) Å	θ = 3.0–25.0°
c = 26.1406 (15) Å	µ = 0.09 mm^−1
β = 98.791 (7)°	T = 150 K
V = 6218.7 (7) Å^3	Block, colorless
Z = 4	0.20 × 0.18 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	5143 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.071
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.652, Tmax = 0.984	k = −19→19
48935 measured reflections	l = −27→31
10890 independent reflections

Refinement

Refinement on F^2	886 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0817P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
10890 reflections	Δρmax = 0.19 e Å^−3
961 parameters	Δρmin = −0.20 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.

Refinement. The single crystal data collection were made on Rigaku Rapid II diffractometer by Mo-Kα radiation at 150K. The data were processed by 'Crystalclear' software package. The structures were then solved by direct methods by 'CrystalStructure' crystallographic software package and the refinement was performed using SHELXL-2019/2.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.62562 (11)	0.41032 (11)	0.50482 (6)	0.0734 (5)
O3	0.64175 (12)	0.68117 (12)	0.63257 (7)	0.0786 (5)
O5	0.92184 (14)	0.26904 (13)	0.48061 (7)	0.0948 (6)
O6	0.89860 (13)	0.57968 (13)	0.56136 (7)	0.0863 (6)
O7	0.91160 (15)	0.13445 (14)	0.67409 (8)	0.1000 (7)
O8	1.15962 (15)	0.37805 (17)	0.65071 (9)	0.1176 (8)
O9	0.68083 (17)	0.21549 (17)	0.79044 (10)	0.1156 (8)
O10	1.02487 (16)	0.35280 (19)	0.80979 (8)	0.1112 (7)
O11	0.44862 (17)	0.41066 (17)	0.68237 (9)	0.1215 (8)
O12	0.76036 (16)	0.52578 (16)	0.80306 (9)	0.1159 (8)
O13	0.74097 (16)	0.25255 (15)	0.56713 (8)	0.1081 (8)
N5	0.75554 (15)	0.33315 (16)	0.63726 (9)	0.0810 (7)
C1	0.57978 (16)	0.55146 (17)	0.60873 (9)	0.0639 (7)
C2	0.57428 (16)	0.48341 (16)	0.57642 (10)	0.0661 (7)
H2A	0.532823	0.441913	0.580616	0.079*
C3	0.62917 (17)	0.47575 (16)	0.53798 (9)	0.0612 (6)
C4	0.69112 (16)	0.53707 (16)	0.53078 (9)	0.0603 (6)
C5	0.69554 (17)	0.60533 (16)	0.56272 (9)	0.0660 (7)
H5	0.736165	0.647381	0.558242	0.079*
C6	0.64089 (17)	0.61253 (16)	0.60121 (9)	0.0634 (7)
C7	0.75205 (17)	0.53017 (17)	0.48923 (9)	0.0693 (7)
H7A	0.716470	0.508280	0.457944	0.083*
H7B	0.772919	0.584520	0.481368	0.083*
C8	0.83418 (17)	0.47580 (17)	0.50520 (9)	0.0616 (7)
C9	0.84070 (18)	0.39889 (17)	0.48388 (9)	0.0665 (7)
H9	0.794481	0.381279	0.458008	0.080*
C10	0.91391 (19)	0.34721 (18)	0.49985 (9)	0.0660 (7)
C11	0.98303 (17)	0.37151 (18)	0.53847 (9)	0.0655 (7)
C12	0.97783 (18)	0.44915 (19)	0.55917 (9)	0.0680 (7)
H12	1.024485	0.466879	0.584758	0.082*
C13	0.90563 (19)	0.50083 (18)	0.54299 (9)	0.0656 (7)
C14	1.06115 (18)	0.31531 (19)	0.55950 (9)	0.0799 (8)
H14A	1.118560	0.344909	0.561543	0.096*
H14B	1.063027	0.269416	0.536053	0.096*
C15	1.05064 (17)	0.28325 (18)	0.61285 (10)	0.0693 (7)
C16	0.98837 (18)	0.22190 (18)	0.61825 (10)	0.0727 (7)
H16	0.956062	0.197826	0.588719	0.087*
C17	0.97263 (18)	0.19516 (18)	0.66647 (11)	0.0728 (7)
C18	1.02084 (19)	0.22880 (19)	0.71111 (10)	0.0732 (8)
C19	1.08329 (19)	0.2895 (2)	0.70569 (11)	0.0814 (8)
H19	1.116930	0.312451	0.735214	0.098*
C20	1.09758 (18)	0.31759 (19)	0.65755 (11)	0.0776 (8)
C21	1.0057 (2)	0.1993 (2)	0.76424 (10)	0.0915 (9)
H21A	0.993785	0.140727	0.762725	0.110*
H21B	1.061201	0.208284	0.788635	0.110*
C22	0.9268 (2)	0.2423 (2)	0.78379 (10)	0.0813 (9)
C23	0.8408 (2)	0.2063 (2)	0.77991 (11)	0.0893 (9)
H23	0.832105	0.153360	0.766719	0.107*
C24	0.7680 (3)	0.2478 (2)	0.79535 (11)	0.0866 (9)
C25	0.7789 (2)	0.3260 (2)	0.81507 (10)	0.0811 (8)
C26	0.8647 (2)	0.3610 (2)	0.82018 (10)	0.0871 (9)
H26	0.873685	0.413270	0.834303	0.105*
C27	0.9374 (2)	0.3198 (2)	0.80469 (10)	0.0851 (9)
C28	0.6985 (2)	0.3736 (2)	0.83055 (10)	0.0942 (10)
H28A	0.656090	0.335489	0.842674	0.113*
H28B	0.720914	0.410320	0.858906	0.113*
C29	0.6482 (2)	0.4234 (2)	0.78584 (10)	0.0780 (8)
C30	0.5692 (2)	0.3955 (2)	0.75650 (12)	0.0846 (9)
H30	0.543575	0.346554	0.765620	0.102*
C31	0.5268 (2)	0.4382 (2)	0.71374 (12)	0.0811 (8)
C32	0.56182 (19)	0.51127 (19)	0.69913 (10)	0.0731 (8)
C33	0.6401 (2)	0.5410 (2)	0.72939 (12)	0.0821 (8)
H33	0.664376	0.590944	0.720923	0.099*
C34	0.6826 (2)	0.4982 (2)	0.77175 (12)	0.0835 (9)
C35	0.51981 (18)	0.55673 (19)	0.65097 (10)	0.0807 (8)
H35A	0.511337	0.613877	0.659482	0.097*
H35B	0.460079	0.533619	0.638298	0.097*
C36	0.54778 (18)	0.35731 (17)	0.50083 (11)	0.0768 (8)
H36A	0.546859	0.329834	0.533660	0.092*	0.549 (9)
H36B	0.492174	0.389519	0.492993	0.092*	0.549 (9)
H36C	0.491123	0.388230	0.493938	0.092*	0.451 (9)
H36D	0.548120	0.325478	0.532211	0.092*	0.451 (9)
C38A	0.6146 (11)	0.1591 (14)	0.4628 (5)	0.0720 (19)	0.549 (9)
O2A	0.5517 (11)	0.1335 (13)	0.4324 (6)	0.097 (3)	0.549 (9)
C37A	0.5507 (13)	0.2980 (14)	0.4614 (6)	0.076 (2)	0.549 (9)
H37A	0.553962	0.327252	0.429441	0.091*	0.549 (9)
H37B	0.492864	0.268707	0.456790	0.091*	0.549 (9)
N1A	0.6231 (11)	0.2377 (11)	0.4679 (4)	0.071 (2)	0.549 (9)
H1A	0.677988	0.256062	0.476067	0.086*	0.549 (9)
N2A	0.6760 (8)	0.1091 (8)	0.4760 (3)	0.0854 (18)	0.549 (9)
H2A1	0.726736	0.128459	0.491963	0.103*	0.549 (9)
C39A	0.6727 (6)	0.0255 (6)	0.4680 (4)	0.110 (2)	0.549 (9)
H39A	0.671104	0.014088	0.431415	0.133*	0.549 (9)
H39B	0.617232	0.003560	0.478351	0.133*	0.549 (9)
C40A	0.7612 (7)	−0.0185 (7)	0.5009 (4)	0.1066 (16)	0.549 (9)
C41A	0.7884 (7)	−0.0694 (7)	0.5421 (4)	0.1199 (18)	0.549 (9)
H41A	0.750734	−0.075098	0.567290	0.144*	0.549 (9)
C42A	0.8678 (8)	−0.1116 (7)	0.5474 (4)	0.129 (2)	0.549 (9)
H42A	0.884325	−0.146034	0.575608	0.155*	0.549 (9)
C43A	0.9218 (7)	−0.1032 (7)	0.5116 (5)	0.128 (2)	0.549 (9)
H43A	0.976352	−0.132549	0.514978	0.153*	0.549 (9)
C44A	0.8988 (7)	−0.0517 (7)	0.4692 (4)	0.137 (2)	0.549 (9)
H44A	0.936229	−0.047514	0.443779	0.164*	0.549 (9)
C45A	0.8189 (7)	−0.0069 (7)	0.4660 (4)	0.125 (2)	0.549 (9)
H45A	0.804667	0.031552	0.439746	0.150*	0.549 (9)
O2B	0.5485 (12)	0.1386 (16)	0.4186 (7)	0.083 (3)	0.451 (9)
C38B	0.6085 (15)	0.1585 (18)	0.4526 (6)	0.075 (2)	0.451 (9)
C37B	0.5607 (16)	0.2987 (17)	0.4522 (8)	0.078 (3)	0.451 (9)
H37C	0.503243	0.274214	0.436518	0.094*	0.451 (9)
H37D	0.587969	0.327971	0.426071	0.094*	0.451 (9)
N1B	0.6252 (14)	0.2360 (13)	0.4800 (6)	0.080 (2)	0.451 (9)
H1B	0.664819	0.244481	0.507159	0.095*	0.451 (9)
N2B	0.6821 (10)	0.1073 (10)	0.4948 (4)	0.093 (2)	0.451 (9)
H2B	0.725341	0.131486	0.515076	0.112*	0.451 (9)
C39B	0.6696 (7)	0.0226 (7)	0.4956 (5)	0.108 (2)	0.451 (9)
H39C	0.626055	0.005815	0.465855	0.130*	0.451 (9)
H39D	0.645533	0.006836	0.526695	0.130*	0.451 (9)
C40B	0.7600 (7)	−0.0189 (8)	0.4944 (4)	0.1065 (18)	0.451 (9)
C41B	0.7598 (6)	−0.0549 (7)	0.5426 (4)	0.115 (2)	0.451 (9)
H41B	0.710659	−0.046639	0.560350	0.138*	0.451 (9)
C42B	0.8332 (7)	−0.1034 (6)	0.5642 (3)	0.124 (2)	0.451 (9)
H42B	0.833168	−0.127548	0.596458	0.149*	0.451 (9)
C43B	0.9068 (6)	−0.1158 (6)	0.5377 (5)	0.126 (2)	0.451 (9)
H43B	0.955877	−0.148252	0.552160	0.151*	0.451 (9)
C44B	0.9069 (6)	−0.0797 (7)	0.4895 (5)	0.130 (2)	0.451 (9)
H44B	0.956076	−0.088048	0.471752	0.157*	0.451 (9)
C45B	0.8335 (8)	−0.0313 (7)	0.4679 (3)	0.121 (2)	0.451 (9)
H45B	0.833567	−0.007138	0.435642	0.146*	0.451 (9)
C46	0.7154 (2)	0.73728 (19)	0.63378 (12)	0.0901 (9)
H46A	0.717782	0.755680	0.598722	0.108*	0.525 (6)
H46B	0.772107	0.708492	0.645800	0.108*	0.525 (6)
H46C	0.716224	0.762694	0.600299	0.108*	0.475 (6)
H46D	0.774003	0.711325	0.645381	0.108*	0.475 (6)
O4A	0.7106 (11)	0.9714 (15)	0.6819 (8)	0.108 (4)	0.525 (6)
C48A	0.6429 (11)	0.9419 (16)	0.6576 (9)	0.084 (2)	0.525 (6)
C47A	0.7103 (10)	0.8110 (11)	0.6673 (7)	0.087 (3)	0.525 (6)
H47A	0.700703	0.794037	0.701595	0.105*	0.525 (6)
H47B	0.767259	0.841464	0.670413	0.105*	0.525 (6)
N3A	0.6335 (13)	0.8633 (11)	0.6436 (5)	0.084 (2)	0.525 (6)
H3A	0.587273	0.844836	0.622787	0.100*	0.525 (6)
N4A	0.5565 (11)	0.9843 (13)	0.6390 (5)	0.090 (2)	0.525 (6)
H4A	0.514585	0.959867	0.617957	0.108*	0.525 (6)
C49A	0.5415 (5)	1.0667 (4)	0.6559 (3)	0.1006 (17)	0.525 (6)
H49A	0.599252	1.096144	0.660775	0.121*	0.525 (6)
H49B	0.519401	1.064660	0.688912	0.121*	0.525 (6)
C50A	0.4724 (5)	1.1128 (5)	0.6169 (3)	0.1028 (18)	0.525 (6)
C51A	0.4855 (4)	1.1273 (5)	0.5661 (3)	0.127 (2)	0.525 (6)
H51A	0.538237	1.108486	0.554517	0.153*	0.525 (6)
C52A	0.4197 (5)	1.1699 (5)	0.5326 (2)	0.138 (2)	0.525 (6)
H52A	0.428396	1.179572	0.498663	0.166*	0.525 (6)
C53A	0.3408 (5)	1.1979 (5)	0.5499 (3)	0.140 (2)	0.525 (6)
H53A	0.296765	1.226434	0.527532	0.168*	0.525 (6)
C54A	0.3277 (4)	1.1834 (5)	0.6007 (3)	0.131 (2)	0.525 (6)
H54A	0.274974	1.202208	0.612255	0.157*	0.525 (6)
C55A	0.3935 (5)	1.1408 (5)	0.6341 (2)	0.124 (2)	0.525 (6)
H55A	0.384814	1.131122	0.668110	0.149*	0.525 (6)
O4B	0.6891 (12)	0.9712 (16)	0.6886 (8)	0.102 (4)	0.475 (6)
C48B	0.6277 (13)	0.9417 (17)	0.6589 (10)	0.080 (2)	0.475 (6)
C47B	0.6902 (11)	0.7989 (12)	0.6736 (7)	0.087 (3)	0.475 (6)
H47C	0.669108	0.768609	0.701451	0.105*	0.475 (6)
H47D	0.745209	0.828264	0.688229	0.105*	0.475 (6)
N3B	0.6230 (15)	0.8563 (12)	0.6544 (6)	0.081 (2)	0.475 (6)
H3B	0.572833	0.836662	0.637991	0.097*	0.475 (6)
N4B	0.5715 (12)	0.9870 (14)	0.6288 (6)	0.091 (2)	0.475 (6)
H4B	0.527426	0.963550	0.608803	0.109*	0.475 (6)
C49B	0.5786 (6)	1.0744 (5)	0.6271 (4)	0.1059 (19)	0.475 (6)
H49C	0.622152	1.088971	0.604343	0.127*	0.475 (6)
H49D	0.602335	1.094390	0.661430	0.127*	0.475 (6)
C50B	0.4904 (7)	1.1158 (8)	0.6087 (4)	0.1045 (18)	0.475 (6)
C51B	0.4736 (7)	1.1659 (6)	0.5671 (4)	0.116 (2)	0.475 (6)
H51B	0.521468	1.173736	0.548265	0.140*	0.475 (6)
C52B	0.3946 (8)	1.2055 (7)	0.5499 (4)	0.127 (2)	0.475 (6)
H52B	0.389372	1.238008	0.520346	0.152*	0.475 (6)
C53B	0.3263 (9)	1.1979 (8)	0.5751 (5)	0.135 (2)	0.475 (6)
H53B	0.272619	1.227287	0.565003	0.161*	0.475 (6)
C54B	0.3335 (9)	1.1457 (8)	0.6172 (4)	0.135 (2)	0.475 (6)
H54B	0.282623	1.135820	0.633331	0.162*	0.475 (6)
C55B	0.4189 (8)	1.1070 (7)	0.6360 (4)	0.122 (2)	0.475 (6)
H55B	0.425805	1.076300	0.666334	0.146*	0.475 (6)
C56	0.8593 (2)	0.2434 (2)	0.43776 (13)	0.1086 (11)
H56A	0.874983	0.189156	0.427819	0.130*
H56B	0.861423	0.280506	0.409431	0.130*
H56C	0.798617	0.243064	0.446685	0.130*
C57	0.9618 (2)	0.6051 (2)	0.60406 (12)	0.1104 (11)
H57A	0.948198	0.660376	0.613092	0.132*
H57B	1.022619	0.602836	0.595385	0.132*
H57C	0.957892	0.569530	0.632907	0.132*
C58	0.8575 (2)	0.0987 (2)	0.63023 (15)	0.1204 (13)
H58A	0.815701	0.059906	0.641414	0.144*
H58B	0.896623	0.071097	0.609604	0.144*
H58C	0.823631	0.140839	0.609981	0.144*
C59	1.1860 (3)	0.4329 (3)	0.69066 (18)	0.182 (2)
H59A	1.132545	0.454135	0.702913	0.218*
H59B	1.219473	0.477358	0.678326	0.218*
H59C	1.224118	0.405403	0.718449	0.218*
C60	0.6671 (3)	0.1327 (3)	0.77892 (18)	0.1529 (17)
H60A	0.699176	0.100228	0.806554	0.184*
H60B	0.689870	0.120232	0.747321	0.184*
H60C	0.602850	0.120512	0.774942	0.184*
C61	1.0326 (3)	0.4372 (3)	0.8090 (2)	0.1614 (19)
H61A	1.095417	0.451999	0.808573	0.194*
H61B	1.012638	0.459789	0.839314	0.194*
H61C	0.995287	0.458465	0.778638	0.194*
C62	0.4123 (3)	0.3358 (3)	0.6924 (2)	0.189 (2)
H62A	0.362091	0.323138	0.665727	0.227*
H62B	0.390905	0.337763	0.725264	0.227*
H62C	0.458584	0.294267	0.693258	0.227*
C63	0.8047 (3)	0.5954 (3)	0.78706 (18)	0.1627 (19)
H63A	0.763236	0.641179	0.783829	0.195*
H63B	0.823807	0.584728	0.754220	0.195*
H63C	0.857272	0.608002	0.812217	0.195*
C64	0.6843 (3)	0.2918 (3)	0.65897 (15)	0.1474 (16)
H64A	0.650013	0.257569	0.633068	0.177*
H64B	0.644259	0.331635	0.670708	0.177*
H64C	0.711158	0.258541	0.687644	0.177*
C65	0.8021 (3)	0.4008 (3)	0.66514 (13)	0.1316 (14)
H65A	0.759391	0.444566	0.667369	0.158*
H65B	0.850303	0.419692	0.647325	0.158*
H65C	0.827572	0.383174	0.699372	0.158*
C66	0.7751 (2)	0.3092 (2)	0.59272 (11)	0.0829 (9)
H66	0.819847	0.338843	0.579294	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0728 (12)	0.0564 (12)	0.0902 (12)	−0.0020 (10)	0.0095 (9)	−0.0117 (10)
O3	0.0809 (12)	0.0637 (14)	0.0912 (12)	0.0038 (11)	0.0134 (9)	−0.0192 (10)
O5	0.1073 (15)	0.0850 (17)	0.0872 (13)	0.0167 (12)	−0.0007 (11)	−0.0277 (12)
O6	0.0845 (13)	0.0796 (16)	0.0961 (13)	−0.0122 (11)	0.0182 (10)	−0.0272 (12)
O7	0.1071 (16)	0.0854 (17)	0.1028 (15)	−0.0224 (14)	0.0012 (12)	0.0122 (12)
O8	0.1035 (16)	0.134 (2)	0.1101 (16)	−0.0527 (16)	0.0006 (13)	−0.0014 (15)
O9	0.1125 (19)	0.097 (2)	0.1443 (19)	−0.0131 (16)	0.0409 (14)	0.0048 (15)
O10	0.0924 (17)	0.125 (2)	0.1089 (16)	−0.0047 (16)	−0.0061 (12)	−0.0237 (15)
O11	0.1072 (17)	0.112 (2)	0.1376 (19)	−0.0312 (16)	−0.0078 (15)	0.0056 (16)
O12	0.1061 (17)	0.109 (2)	0.1220 (17)	−0.0249 (15)	−0.0149 (14)	0.0053 (14)
O13	0.1306 (19)	0.0932 (19)	0.0878 (14)	0.0077 (14)	−0.0241 (13)	−0.0129 (13)
N5	0.0830 (16)	0.094 (2)	0.0665 (14)	0.0043 (14)	0.0121 (12)	0.0049 (13)
C1	0.0585 (15)	0.0600 (19)	0.0726 (16)	0.0112 (14)	0.0082 (12)	0.0016 (14)
C2	0.0585 (15)	0.0569 (19)	0.0819 (17)	0.0047 (13)	0.0077 (13)	0.0061 (14)
C3	0.0646 (16)	0.0464 (18)	0.0697 (16)	0.0083 (14)	0.0011 (12)	−0.0029 (13)
C4	0.0658 (16)	0.0461 (17)	0.0670 (15)	0.0062 (14)	0.0039 (12)	0.0018 (13)
C5	0.0678 (16)	0.0528 (18)	0.0760 (16)	0.0026 (13)	0.0069 (13)	0.0041 (14)
C6	0.0643 (16)	0.0532 (19)	0.0702 (16)	0.0089 (14)	0.0024 (13)	−0.0053 (13)
C7	0.0819 (18)	0.0620 (19)	0.0654 (15)	−0.0013 (15)	0.0156 (13)	0.0032 (13)
C8	0.0686 (16)	0.066 (2)	0.0519 (13)	−0.0036 (15)	0.0159 (12)	−0.0018 (13)
C9	0.0747 (18)	0.072 (2)	0.0534 (14)	−0.0020 (16)	0.0098 (12)	−0.0107 (14)
C10	0.0786 (18)	0.064 (2)	0.0574 (15)	0.0018 (16)	0.0154 (13)	−0.0085 (14)
C11	0.0630 (16)	0.081 (2)	0.0547 (14)	0.0018 (15)	0.0160 (12)	−0.0013 (14)
C12	0.0653 (17)	0.083 (2)	0.0568 (15)	−0.0124 (16)	0.0141 (12)	−0.0117 (15)
C13	0.0723 (18)	0.064 (2)	0.0650 (15)	−0.0089 (16)	0.0243 (14)	−0.0111 (14)
C14	0.0689 (17)	0.099 (2)	0.0733 (17)	0.0080 (17)	0.0156 (13)	−0.0006 (16)
C15	0.0577 (16)	0.078 (2)	0.0706 (17)	0.0058 (15)	0.0028 (13)	0.0011 (14)
C16	0.0725 (18)	0.071 (2)	0.0689 (17)	0.0034 (16)	−0.0063 (13)	−0.0033 (14)
C17	0.0642 (17)	0.063 (2)	0.087 (2)	0.0017 (15)	−0.0024 (14)	0.0076 (15)
C18	0.0694 (18)	0.074 (2)	0.0723 (18)	0.0104 (16)	−0.0012 (14)	0.0105 (15)
C19	0.0767 (19)	0.089 (2)	0.0717 (18)	0.0022 (18)	−0.0116 (14)	−0.0010 (16)
C20	0.0625 (17)	0.083 (2)	0.083 (2)	−0.0093 (16)	−0.0012 (14)	−0.0014 (16)
C21	0.098 (2)	0.097 (3)	0.0741 (18)	0.020 (2)	−0.0046 (16)	0.0201 (16)
C22	0.096 (2)	0.086 (3)	0.0582 (16)	0.011 (2)	0.0009 (15)	0.0175 (16)
C23	0.106 (3)	0.078 (2)	0.084 (2)	0.003 (2)	0.0143 (18)	0.0148 (16)
C24	0.099 (3)	0.085 (3)	0.0765 (19)	−0.004 (2)	0.0163 (17)	0.0161 (18)
C25	0.100 (2)	0.089 (3)	0.0554 (15)	0.007 (2)	0.0126 (15)	0.0134 (16)
C26	0.103 (2)	0.097 (3)	0.0582 (16)	−0.003 (2)	0.0017 (15)	0.0004 (15)
C27	0.086 (2)	0.103 (3)	0.0621 (17)	0.004 (2)	−0.0031 (15)	0.0037 (17)
C28	0.110 (2)	0.107 (3)	0.0696 (18)	0.000 (2)	0.0252 (17)	0.0061 (17)
C29	0.085 (2)	0.082 (2)	0.0719 (18)	−0.0001 (18)	0.0287 (16)	−0.0066 (16)
C30	0.086 (2)	0.085 (2)	0.088 (2)	−0.0121 (19)	0.0284 (17)	0.0017 (18)
C31	0.0705 (19)	0.086 (3)	0.088 (2)	−0.0102 (18)	0.0167 (16)	−0.0110 (18)
C32	0.0691 (18)	0.074 (2)	0.0799 (18)	0.0019 (16)	0.0241 (15)	−0.0043 (16)
C33	0.0755 (19)	0.080 (2)	0.093 (2)	−0.0063 (17)	0.0188 (16)	0.0029 (17)
C34	0.077 (2)	0.090 (3)	0.084 (2)	−0.0061 (19)	0.0125 (16)	−0.0091 (18)
C35	0.0725 (17)	0.082 (2)	0.0904 (19)	0.0143 (16)	0.0227 (15)	−0.0012 (16)
C36	0.0721 (17)	0.0569 (19)	0.0954 (19)	0.0053 (15)	−0.0062 (14)	−0.0084 (15)
C38A	0.075 (3)	0.057 (3)	0.077 (4)	0.009 (3)	−0.013 (3)	−0.010 (4)
O2A	0.098 (4)	0.069 (4)	0.109 (7)	0.000 (3)	−0.027 (5)	−0.026 (6)
C37A	0.075 (4)	0.061 (3)	0.085 (5)	0.011 (3)	−0.011 (4)	−0.008 (4)
N1A	0.065 (3)	0.066 (3)	0.074 (4)	0.007 (2)	−0.023 (3)	−0.013 (4)
N2A	0.095 (3)	0.062 (3)	0.094 (4)	0.019 (2)	−0.003 (4)	0.009 (4)
C39A	0.121 (3)	0.085 (3)	0.120 (4)	0.010 (3)	0.002 (4)	−0.001 (4)
C40A	0.113 (3)	0.082 (3)	0.124 (3)	0.033 (3)	0.014 (3)	0.013 (3)
C41A	0.123 (4)	0.095 (4)	0.140 (4)	0.039 (3)	0.013 (3)	0.013 (3)
C42A	0.124 (5)	0.106 (4)	0.152 (4)	0.043 (4)	0.004 (4)	0.009 (4)
C43A	0.122 (4)	0.108 (4)	0.145 (5)	0.057 (3)	−0.002 (3)	0.011 (4)
C44A	0.131 (4)	0.117 (5)	0.157 (5)	0.056 (4)	0.008 (4)	0.015 (4)
C45A	0.122 (4)	0.106 (5)	0.145 (4)	0.042 (3)	0.017 (3)	0.017 (3)
O2B	0.074 (5)	0.079 (6)	0.092 (7)	0.000 (4)	−0.005 (4)	−0.028 (5)
C38B	0.079 (4)	0.062 (3)	0.082 (5)	0.008 (3)	0.010 (4)	−0.004 (4)
C37B	0.078 (5)	0.062 (4)	0.087 (5)	0.012 (4)	−0.012 (4)	−0.013 (4)
N1B	0.080 (3)	0.066 (3)	0.084 (6)	0.015 (3)	−0.013 (4)	−0.011 (4)
N2B	0.105 (3)	0.062 (3)	0.107 (5)	0.002 (3)	0.000 (4)	−0.007 (5)
C39B	0.118 (4)	0.082 (4)	0.121 (5)	0.016 (3)	0.008 (4)	0.015 (4)
C40B	0.113 (3)	0.084 (3)	0.122 (4)	0.029 (3)	0.016 (3)	0.010 (3)
C41B	0.116 (5)	0.096 (4)	0.132 (4)	0.032 (4)	0.016 (4)	0.012 (4)
C42B	0.120 (5)	0.102 (5)	0.145 (5)	0.028 (4)	0.005 (4)	0.014 (4)
C43B	0.117 (5)	0.107 (4)	0.150 (5)	0.044 (4)	0.006 (4)	0.015 (4)
C44B	0.129 (4)	0.110 (5)	0.150 (5)	0.047 (4)	0.011 (4)	0.019 (4)
C45B	0.121 (4)	0.103 (5)	0.140 (4)	0.046 (4)	0.017 (3)	0.015 (4)
C46	0.0774 (19)	0.077 (2)	0.111 (2)	0.0006 (17)	−0.0009 (16)	−0.0283 (17)
O4A	0.087 (6)	0.086 (5)	0.141 (7)	−0.024 (5)	−0.013 (5)	−0.009 (5)
C48A	0.087 (5)	0.067 (3)	0.097 (4)	−0.008 (4)	0.010 (4)	−0.014 (3)
C47A	0.079 (5)	0.077 (5)	0.103 (5)	−0.002 (4)	0.002 (4)	−0.021 (4)
N3A	0.076 (4)	0.071 (4)	0.099 (5)	−0.003 (3)	−0.002 (4)	−0.016 (4)
N4A	0.091 (4)	0.066 (3)	0.109 (4)	−0.010 (3)	0.004 (3)	−0.015 (4)
C49A	0.111 (4)	0.070 (3)	0.120 (4)	−0.005 (3)	0.015 (3)	−0.014 (3)
C50A	0.109 (4)	0.071 (3)	0.130 (4)	−0.014 (3)	0.020 (3)	0.005 (3)
C51A	0.127 (4)	0.110 (5)	0.148 (4)	−0.007 (4)	0.029 (3)	0.023 (4)
C52A	0.148 (5)	0.125 (5)	0.144 (4)	−0.005 (4)	0.030 (4)	0.031 (4)
C53A	0.156 (4)	0.117 (4)	0.148 (4)	0.005 (4)	0.027 (4)	0.028 (4)
C54A	0.150 (4)	0.104 (4)	0.139 (4)	0.021 (4)	0.026 (4)	0.031 (4)
C55A	0.136 (4)	0.096 (4)	0.139 (4)	0.021 (4)	0.017 (3)	0.014 (3)
O4B	0.098 (7)	0.080 (5)	0.119 (6)	−0.014 (6)	−0.017 (6)	−0.033 (5)
C48B	0.078 (4)	0.064 (3)	0.095 (4)	−0.016 (4)	0.006 (4)	−0.016 (3)
C47B	0.081 (5)	0.075 (5)	0.101 (5)	−0.006 (4)	0.000 (4)	−0.025 (4)
N3B	0.077 (4)	0.066 (3)	0.098 (5)	−0.003 (3)	0.009 (4)	−0.019 (4)
N4B	0.093 (5)	0.066 (3)	0.109 (5)	−0.014 (4)	0.000 (4)	−0.013 (4)
C49B	0.112 (4)	0.069 (3)	0.133 (4)	−0.015 (3)	0.005 (3)	0.000 (4)
C50B	0.113 (3)	0.072 (3)	0.128 (4)	−0.014 (3)	0.016 (3)	0.005 (3)
C51B	0.118 (4)	0.091 (5)	0.141 (4)	−0.004 (4)	0.024 (3)	0.016 (4)
C52B	0.129 (4)	0.105 (4)	0.148 (4)	0.006 (4)	0.029 (4)	0.025 (4)
C53B	0.149 (4)	0.111 (4)	0.146 (5)	0.015 (4)	0.031 (4)	0.019 (4)
C54B	0.147 (4)	0.111 (5)	0.153 (5)	0.000 (4)	0.041 (4)	0.016 (4)
C55B	0.139 (4)	0.090 (4)	0.139 (4)	0.004 (4)	0.032 (3)	0.011 (3)
C56	0.108 (2)	0.101 (3)	0.115 (2)	0.000 (2)	0.010 (2)	−0.046 (2)
C57	0.122 (3)	0.108 (3)	0.103 (2)	−0.026 (2)	0.020 (2)	−0.045 (2)
C58	0.111 (3)	0.087 (3)	0.148 (3)	−0.029 (2)	−0.028 (2)	0.026 (2)
C59	0.211 (5)	0.168 (5)	0.158 (4)	−0.114 (4)	−0.001 (3)	−0.024 (4)
C60	0.151 (4)	0.118 (4)	0.199 (5)	−0.038 (3)	0.058 (3)	−0.011 (3)
C61	0.112 (3)	0.134 (5)	0.236 (5)	−0.029 (3)	0.021 (3)	−0.060 (4)
C62	0.151 (4)	0.156 (5)	0.241 (6)	−0.075 (4)	−0.027 (4)	0.034 (4)
C63	0.133 (3)	0.154 (5)	0.187 (4)	−0.068 (3)	−0.021 (3)	0.030 (3)
C64	0.151 (3)	0.177 (5)	0.128 (3)	−0.022 (3)	0.065 (3)	0.020 (3)
C65	0.160 (3)	0.136 (4)	0.095 (2)	−0.009 (3)	0.007 (2)	−0.028 (2)
C66	0.083 (2)	0.102 (3)	0.0623 (18)	0.0095 (19)	0.0071 (15)	0.0061 (17)

Geometric parameters (Å, º)

O1—C3	1.370 (3)	C44A—C45A	1.379 (11)
O1—C36	1.429 (3)	C44A—H44A	0.9300
O3—C6	1.386 (3)	C45A—H45A	0.9300
O3—C46	1.417 (3)	O2B—C38B	1.2008 (11)
O5—C10	1.381 (3)	C38B—N1B	1.45 (4)
O5—C56	1.402 (3)	C38B—N2B	1.65 (3)
O6—C13	1.381 (3)	C37B—N1B	1.51 (4)
O6—C57	1.404 (3)	C37B—H37C	0.9700
O7—C17	1.373 (3)	C37B—H37D	0.9700
O7—C58	1.419 (4)	N1B—H1B	0.8600
O8—C20	1.376 (3)	N2B—C39B	1.394 (16)
O8—C59	1.385 (4)	N2B—H2B	0.8600
O9—C24	1.379 (4)	C39B—C40B	1.500 (13)
O9—C60	1.390 (4)	C39B—H39C	0.9700
O10—C61	1.380 (5)	C39B—H39D	0.9700
O10—C27	1.386 (4)	C40B—C41B	1.3900
O11—C62	1.374 (4)	C40B—C45B	1.3900
O11—C31	1.385 (3)	C41B—C42B	1.3900
O12—C34	1.380 (3)	C41B—H41B	0.9300
O12—C63	1.406 (4)	C42B—C43B	1.3900
O13—C66	1.204 (3)	C42B—H42B	0.9300
N5—C66	1.301 (3)	C43B—C44B	1.3900
N5—C65	1.437 (4)	C43B—H43B	0.9300
N5—C64	1.437 (4)	C44B—C45B	1.3900
C1—C6	1.378 (3)	C44B—H44B	0.9300
C1—C2	1.389 (3)	C45B—H45B	0.9300
C1—C35	1.520 (3)	C46—C47A	1.495 (18)
C2—C3	1.390 (3)	C46—C47B	1.53 (2)
C2—H2A	0.9300	C46—H46A	0.9700
C3—C4	1.387 (3)	C46—H46B	0.9700
C4—C5	1.386 (3)	C46—H46C	0.9700
C4—C7	1.517 (3)	C46—H46D	0.9700
C5—C6	1.388 (3)	O4A—C48A	1.2008 (11)
C5—H5	0.9300	C48A—N3A	1.33 (3)
C7—C8	1.509 (3)	C48A—N4A	1.47 (3)
C7—H7A	0.9700	C47A—N3A	1.48 (2)
C7—H7B	0.9700	C47A—H47A	0.9700
C8—C9	1.381 (3)	C47A—H47B	0.9700
C8—C13	1.392 (3)	N3A—H3A	0.8600
C9—C10	1.384 (3)	N4A—C49A	1.44 (2)
C9—H9	0.9300	N4A—H4A	0.8600
C10—C11	1.380 (3)	C49A—C50A	1.526 (8)
C11—C12	1.383 (4)	C49A—H49A	0.9700
C11—C14	1.510 (3)	C49A—H49B	0.9700
C12—C13	1.374 (4)	C50A—C51A	1.3900
C12—H12	0.9300	C50A—C55A	1.3900
C14—C15	1.519 (3)	C51A—C52A	1.3900
C14—H14A	0.9700	C51A—H51A	0.9300
C14—H14B	0.9700	C52A—C53A	1.3900
C15—C16	1.380 (4)	C52A—H52A	0.9300
C15—C20	1.383 (4)	C53A—C54A	1.3900
C16—C17	1.386 (4)	C53A—H53A	0.9300
C16—H16	0.9300	C54A—C55A	1.3900
C17—C18	1.384 (4)	C54A—H54A	0.9300
C18—C19	1.375 (4)	C55A—H55A	0.9300
C18—C21	1.518 (4)	O4B—C48B	1.2008 (11)
C19—C20	1.385 (4)	C48B—N4B	1.29 (3)
C19—H19	0.9300	C48B—N3B	1.40 (3)
C21—C22	1.514 (4)	C47B—N3B	1.40 (2)
C21—H21A	0.9700	C47B—H47C	0.9700
C21—H21B	0.9700	C47B—H47D	0.9700
C22—C27	1.376 (4)	N3B—H3B	0.8600
C22—C23	1.389 (4)	N4B—C49B	1.43 (2)
C23—C24	1.383 (4)	N4B—H4B	0.8600
C23—H23	0.9300	C49B—C50B	1.481 (11)
C24—C25	1.374 (4)	C49B—H49C	0.9700
C25—C26	1.378 (4)	C49B—H49D	0.9700
C25—C28	1.524 (4)	C50B—C51B	1.352 (13)
C26—C27	1.379 (4)	C50B—C55B	1.370 (8)
C26—H26	0.9300	C51B—C52B	1.349 (12)
C28—C29	1.520 (4)	C51B—H51B	0.9300
C28—H28A	0.9700	C52B—C53B	1.293 (14)
C28—H28B	0.9700	C52B—H52B	0.9300
C29—C30	1.372 (4)	C53B—C54B	1.380 (14)
C29—C34	1.392 (4)	C53B—H53B	0.9300
C30—C31	1.383 (4)	C54B—C55B	1.429 (14)
C30—H30	0.9300	C54B—H54B	0.9300
C31—C32	1.376 (4)	C55B—H55B	0.9300
C32—C33	1.385 (4)	C56—H56A	0.9600
C32—C35	1.510 (4)	C56—H56B	0.9600
C33—C34	1.376 (4)	C56—H56C	0.9600
C33—H33	0.9300	C57—H57A	0.9600
C35—H35A	0.9700	C57—H57B	0.9600
C35—H35B	0.9700	C57—H57C	0.9600
C36—C37A	1.418 (18)	C58—H58A	0.9600
C36—C37B	1.62 (2)	C58—H58B	0.9600
C36—H36A	0.9700	C58—H58C	0.9600
C36—H36B	0.9700	C59—H59A	0.9600
C36—H36C	0.9700	C59—H59B	0.9600
C36—H36D	0.9700	C59—H59C	0.9600
C38A—O2A	1.2011 (10)	C60—H60A	0.9600
C38A—N2A	1.23 (3)	C60—H60B	0.9600
C38A—N1A	1.29 (3)	C60—H60C	0.9600
C37A—N1A	1.44 (3)	C61—H61A	0.9600
C37A—H37A	0.9700	C61—H61B	0.9600
C37A—H37B	0.9700	C61—H61C	0.9600
N1A—H1A	0.8600	C62—H62A	0.9600
N2A—C39A	1.378 (13)	C62—H62B	0.9600
N2A—H2A1	0.8600	C62—H62C	0.9600
C39A—C40A	1.619 (12)	C63—H63A	0.9600
C39A—H39A	0.9700	C63—H63B	0.9600
C39A—H39B	0.9700	C63—H63C	0.9600
C40A—C45A	1.354 (7)	C64—H64A	0.9600
C40A—C41A	1.369 (10)	C64—H64B	0.9600
C41A—C42A	1.348 (11)	C64—H64C	0.9600
C41A—H41A	0.9300	C65—H65A	0.9600
C42A—C43A	1.325 (12)	C65—H65B	0.9600
C42A—H42A	0.9300	C65—H65C	0.9600
C43A—C44A	1.391 (11)	C66—H66	0.9300
C43A—H43A	0.9300
C3—O1—C36	118.0 (2)	N1B—C37B—H37C	111.9
C6—O3—C46	118.1 (2)	C36—C37B—H37C	111.9
C10—O5—C56	118.9 (2)	N1B—C37B—H37D	111.9
C13—O6—C57	118.3 (2)	C36—C37B—H37D	111.9
C17—O7—C58	118.7 (2)	H37C—C37B—H37D	109.6
C20—O8—C59	118.7 (3)	C38B—N1B—C37B	107.8 (19)
C24—O9—C60	119.6 (3)	C38B—N1B—H1B	126.1
C61—O10—C27	117.6 (3)	C37B—N1B—H1B	126.1
C62—O11—C31	119.3 (3)	C39B—N2B—C38B	115.8 (14)
C34—O12—C63	118.0 (3)	C39B—N2B—H2B	122.1
C66—N5—C65	122.0 (3)	C38B—N2B—H2B	122.1
C66—N5—C64	119.2 (3)	N2B—C39B—C40B	109.0 (11)
C65—N5—C64	118.8 (3)	N2B—C39B—H39C	109.9
C6—C1—C2	117.9 (2)	C40B—C39B—H39C	109.9
C6—C1—C35	122.0 (2)	N2B—C39B—H39D	109.9
C2—C1—C35	120.0 (2)	C40B—C39B—H39D	109.9
C1—C2—C3	121.7 (2)	H39C—C39B—H39D	108.3
C1—C2—H2A	119.2	C41B—C40B—C45B	120.0
C3—C2—H2A	119.2	C41B—C40B—C39B	92.7 (9)
O1—C3—C4	115.9 (2)	C45B—C40B—C39B	147.3 (9)
O1—C3—C2	123.9 (2)	C42B—C41B—C40B	120.0
C4—C3—C2	120.2 (2)	C42B—C41B—H41B	120.0
C5—C4—C3	117.9 (2)	C40B—C41B—H41B	120.0
C5—C4—C7	120.8 (2)	C43B—C42B—C41B	120.0
C3—C4—C7	121.3 (2)	C43B—C42B—H42B	120.0
C4—C5—C6	121.7 (2)	C41B—C42B—H42B	120.0
C4—C5—H5	119.2	C42B—C43B—C44B	120.0
C6—C5—H5	119.2	C42B—C43B—H43B	120.0
C1—C6—O3	116.4 (2)	C44B—C43B—H43B	120.0
C1—C6—C5	120.6 (2)	C43B—C44B—C45B	120.0
O3—C6—C5	122.9 (2)	C43B—C44B—H44B	120.0
C8—C7—C4	112.67 (19)	C45B—C44B—H44B	120.0
C8—C7—H7A	109.1	C44B—C45B—C40B	120.0
C4—C7—H7A	109.1	C44B—C45B—H45B	120.0
C8—C7—H7B	109.1	C40B—C45B—H45B	120.0
C4—C7—H7B	109.1	O3—C46—C47A	115.1 (6)
H7A—C7—H7B	107.8	O3—C46—C47B	100.0 (6)
C9—C8—C13	117.4 (2)	O3—C46—H46A	108.5
C9—C8—C7	121.6 (2)	C47A—C46—H46A	108.5
C13—C8—C7	121.0 (2)	O3—C46—H46B	108.5
C8—C9—C10	122.0 (2)	C47A—C46—H46B	108.5
C8—C9—H9	119.0	H46A—C46—H46B	107.5
C10—C9—H9	119.0	O3—C46—H46C	111.8
C11—C10—O5	115.9 (3)	C47B—C46—H46C	111.8
C11—C10—C9	120.2 (2)	O3—C46—H46D	111.8
O5—C10—C9	123.9 (2)	C47B—C46—H46D	111.8
C10—C11—C12	118.0 (3)	H46C—C46—H46D	109.5
C10—C11—C14	122.1 (3)	O4A—C48A—N3A	125 (2)
C12—C11—C14	119.8 (2)	O4A—C48A—N4A	127 (2)
C13—C12—C11	121.8 (2)	N3A—C48A—N4A	108.3 (15)
C13—C12—H12	119.1	N3A—C47A—C46	108.8 (11)
C11—C12—H12	119.1	N3A—C47A—H47A	109.9
C12—C13—O6	124.0 (2)	C46—C47A—H47A	109.9
C12—C13—C8	120.5 (3)	N3A—C47A—H47B	109.9
O6—C13—C8	115.5 (3)	C46—C47A—H47B	109.9
C11—C14—C15	111.3 (2)	H47A—C47A—H47B	108.3
C11—C14—H14A	109.4	C48A—N3A—C47A	113.5 (15)
C15—C14—H14A	109.4	C48A—N3A—H3A	123.2
C11—C14—H14B	109.4	C47A—N3A—H3A	123.2
C15—C14—H14B	109.4	C49A—N4A—C48A	120.3 (16)
H14A—C14—H14B	108.0	C49A—N4A—H4A	119.9
C16—C15—C20	117.6 (2)	C48A—N4A—H4A	119.9
C16—C15—C14	120.4 (2)	N4A—C49A—C50A	111.9 (8)
C20—C15—C14	121.9 (3)	N4A—C49A—H49A	109.2
C15—C16—C17	121.8 (3)	C50A—C49A—H49A	109.2
C15—C16—H16	119.1	N4A—C49A—H49B	109.2
C17—C16—H16	119.1	C50A—C49A—H49B	109.2
O7—C17—C18	115.3 (3)	H49A—C49A—H49B	107.9
O7—C17—C16	124.3 (3)	C51A—C50A—C55A	120.0
C18—C17—C16	120.4 (3)	C51A—C50A—C49A	123.1 (6)
C19—C18—C17	117.7 (3)	C55A—C50A—C49A	116.9 (6)
C19—C18—C21	121.2 (3)	C50A—C51A—C52A	120.0
C17—C18—C21	121.1 (3)	C50A—C51A—H51A	120.0
C18—C19—C20	121.9 (3)	C52A—C51A—H51A	120.0
C18—C19—H19	119.0	C51A—C52A—C53A	120.0
C20—C19—H19	119.0	C51A—C52A—H52A	120.0
O8—C20—C15	116.0 (3)	C53A—C52A—H52A	120.0
O8—C20—C19	123.5 (3)	C54A—C53A—C52A	120.0
C15—C20—C19	120.5 (3)	C54A—C53A—H53A	120.0
C22—C21—C18	113.0 (2)	C52A—C53A—H53A	120.0
C22—C21—H21A	109.0	C55A—C54A—C53A	120.0
C18—C21—H21A	109.0	C55A—C54A—H54A	120.0
C22—C21—H21B	109.0	C53A—C54A—H54A	120.0
C18—C21—H21B	109.0	C54A—C55A—C50A	120.0
H21A—C21—H21B	107.8	C54A—C55A—H55A	120.0
C27—C22—C23	117.7 (3)	C50A—C55A—H55A	120.0
C27—C22—C21	120.8 (3)	O4B—C48B—N4B	121 (3)
C23—C22—C21	121.5 (3)	O4B—C48B—N3B	118 (2)
C24—C23—C22	121.0 (3)	N4B—C48B—N3B	120.1 (18)
C24—C23—H23	119.5	N3B—C47B—C46	115.3 (12)
C22—C23—H23	119.5	N3B—C47B—H47C	108.4
C25—C24—O9	116.3 (3)	C46—C47B—H47C	108.4
C25—C24—C23	120.8 (3)	N3B—C47B—H47D	108.4
O9—C24—C23	122.9 (3)	C46—C47B—H47D	108.4
C24—C25—C26	118.2 (3)	H47C—C47B—H47D	107.5
C24—C25—C28	121.4 (3)	C48B—N3B—C47B	127.8 (16)
C26—C25—C28	120.4 (3)	C48B—N3B—H3B	116.1
C25—C26—C27	121.1 (3)	C47B—N3B—H3B	116.1
C25—C26—H26	119.4	C48B—N4B—C49B	123.2 (19)
C27—C26—H26	119.4	C48B—N4B—H4B	118.4
C22—C27—C26	121.1 (3)	C49B—N4B—H4B	118.4
C22—C27—O10	116.3 (3)	N4B—C49B—C50B	113.6 (10)
C26—C27—O10	122.7 (3)	N4B—C49B—H49C	108.8
C29—C28—C25	112.1 (2)	C50B—C49B—H49C	108.8
C29—C28—H28A	109.2	N4B—C49B—H49D	108.8
C25—C28—H28A	109.2	C50B—C49B—H49D	108.8
C29—C28—H28B	109.2	H49C—C49B—H49D	107.7
C25—C28—H28B	109.2	C51B—C50B—C55B	114.9 (10)
H28A—C28—H28B	107.9	C51B—C50B—C49B	125.5 (9)
C30—C29—C34	117.1 (3)	C55B—C50B—C49B	119.6 (10)
C30—C29—C28	121.8 (3)	C52B—C51B—C50B	126.9 (10)
C34—C29—C28	121.0 (3)	C52B—C51B—H51B	116.6
C29—C30—C31	121.8 (3)	C50B—C51B—H51B	116.6
C29—C30—H30	119.1	C53B—C52B—C51B	119.1 (11)
C31—C30—H30	119.1	C53B—C52B—H52B	120.4
C32—C31—C30	121.1 (3)	C51B—C52B—H52B	120.4
C32—C31—O11	115.5 (3)	C52B—C53B—C54B	119.7 (12)
C30—C31—O11	123.4 (3)	C52B—C53B—H53B	120.2
C31—C32—C33	117.4 (3)	C54B—C53B—H53B	120.2
C31—C32—C35	122.1 (3)	C53B—C54B—C55B	120.1 (12)
C33—C32—C35	120.4 (3)	C53B—C54B—H54B	119.9
C34—C33—C32	121.4 (3)	C55B—C54B—H54B	119.9
C34—C33—H33	119.3	C50B—C55B—C54B	119.0 (10)
C32—C33—H33	119.3	C50B—C55B—H55B	120.5
C33—C34—O12	123.3 (3)	C54B—C55B—H55B	120.5
C33—C34—C29	121.1 (3)	O5—C56—H56A	109.5
O12—C34—C29	115.6 (3)	O5—C56—H56B	109.5
C32—C35—C1	111.5 (2)	H56A—C56—H56B	109.5
C32—C35—H35A	109.3	O5—C56—H56C	109.5
C1—C35—H35A	109.3	H56A—C56—H56C	109.5
C32—C35—H35B	109.3	H56B—C56—H56C	109.5
C1—C35—H35B	109.3	O6—C57—H57A	109.5
H35A—C35—H35B	108.0	O6—C57—H57B	109.5
C37A—C36—O1	110.6 (8)	H57A—C57—H57B	109.5
O1—C36—C37B	102.9 (9)	O6—C57—H57C	109.5
C37A—C36—H36A	109.5	H57A—C57—H57C	109.5
O1—C36—H36A	109.5	H57B—C57—H57C	109.5
C37A—C36—H36B	109.5	O7—C58—H58A	109.5
O1—C36—H36B	109.5	O7—C58—H58B	109.5
H36A—C36—H36B	108.1	H58A—C58—H58B	109.5
O1—C36—H36C	111.2	O7—C58—H58C	109.5
C37B—C36—H36C	111.2	H58A—C58—H58C	109.5
O1—C36—H36D	111.2	H58B—C58—H58C	109.5
C37B—C36—H36D	111.2	O8—C59—H59A	109.5
H36C—C36—H36D	109.1	O8—C59—H59B	109.5
O2A—C38A—N2A	114.7 (19)	H59A—C59—H59B	109.5
O2A—C38A—N1A	117.8 (18)	O8—C59—H59C	109.5
N2A—C38A—N1A	124.9 (16)	H59A—C59—H59C	109.5
C36—C37A—N1A	118.9 (14)	H59B—C59—H59C	109.5
C36—C37A—H37A	107.6	O9—C60—H60A	109.5
N1A—C37A—H37A	107.6	O9—C60—H60B	109.5
C36—C37A—H37B	107.6	H60A—C60—H60B	109.5
N1A—C37A—H37B	107.6	O9—C60—H60C	109.5
H37A—C37A—H37B	107.0	H60A—C60—H60C	109.5
C38A—N1A—C37A	127.2 (18)	H60B—C60—H60C	109.5
C38A—N1A—H1A	116.4	O10—C61—H61A	109.5
C37A—N1A—H1A	116.4	O10—C61—H61B	109.5
C38A—N2A—C39A	127.2 (14)	H61A—C61—H61B	109.5
C38A—N2A—H2A1	116.4	O10—C61—H61C	109.5
C39A—N2A—H2A1	116.4	H61A—C61—H61C	109.5
N2A—C39A—C40A	110.5 (8)	H61B—C61—H61C	109.5
N2A—C39A—H39A	109.6	O11—C62—H62A	109.5
C40A—C39A—H39A	109.6	O11—C62—H62B	109.5
N2A—C39A—H39B	109.6	H62A—C62—H62B	109.5
C40A—C39A—H39B	109.6	O11—C62—H62C	109.5
H39A—C39A—H39B	108.1	H62A—C62—H62C	109.5
C45A—C40A—C41A	118.3 (7)	H62B—C62—H62C	109.5
C45A—C40A—C39A	96.9 (9)	O12—C63—H63A	109.5
C41A—C40A—C39A	143.4 (9)	O12—C63—H63B	109.5
C42A—C41A—C40A	122.4 (8)	H63A—C63—H63B	109.5
C42A—C41A—H41A	118.8	O12—C63—H63C	109.5
C40A—C41A—H41A	118.8	H63A—C63—H63C	109.5
C43A—C42A—C41A	118.9 (9)	H63B—C63—H63C	109.5
C43A—C42A—H42A	120.6	N5—C64—H64A	109.5
C41A—C42A—H42A	120.6	N5—C64—H64B	109.5
C42A—C43A—C44A	121.6 (9)	H64A—C64—H64B	109.5
C42A—C43A—H43A	119.2	N5—C64—H64C	109.5
C44A—C43A—H43A	119.2	H64A—C64—H64C	109.5
C45A—C44A—C43A	118.0 (9)	H64B—C64—H64C	109.5
C45A—C44A—H44A	121.0	N5—C65—H65A	109.5
C43A—C44A—H44A	121.0	N5—C65—H65B	109.5
C40A—C45A—C44A	120.5 (8)	H65A—C65—H65B	109.5
C40A—C45A—H45A	119.8	N5—C65—H65C	109.5
C44A—C45A—H45A	119.8	H65A—C65—H65C	109.5
O2B—C38B—N1B	130 (3)	H65B—C65—H65C	109.5
O2B—C38B—N2B	134 (2)	O13—C66—N5	126.6 (3)
N1B—C38B—N2B	93.7 (13)	O13—C66—H66	116.7
N1B—C37B—C36	99.4 (15)	N5—C66—H66	116.7
C6—C1—C2—C3	0.9 (4)	C28—C29—C30—C31	−175.7 (3)
C35—C1—C2—C3	−178.8 (2)	C29—C30—C31—C32	−0.6 (4)
C36—O1—C3—C4	−163.3 (2)	C29—C30—C31—O11	178.0 (3)
C36—O1—C3—C2	15.7 (3)	C62—O11—C31—C32	176.1 (4)
C1—C2—C3—O1	−179.3 (2)	C62—O11—C31—C30	−2.6 (5)
C1—C2—C3—C4	−0.4 (4)	C30—C31—C32—C33	−1.2 (4)
O1—C3—C4—C5	178.6 (2)	O11—C31—C32—C33	−179.9 (2)
C2—C3—C4—C5	−0.4 (3)	C30—C31—C32—C35	176.6 (3)
O1—C3—C4—C7	−1.2 (3)	O11—C31—C32—C35	−2.2 (4)
C2—C3—C4—C7	179.8 (2)	C31—C32—C33—C34	1.6 (4)
C3—C4—C5—C6	0.7 (4)	C35—C32—C33—C34	−176.2 (3)
C7—C4—C5—C6	−179.5 (2)	C32—C33—C34—O12	−179.7 (3)
C2—C1—C6—O3	177.2 (2)	C32—C33—C34—C29	−0.2 (4)
C35—C1—C6—O3	−3.1 (3)	C63—O12—C34—C33	−8.4 (5)
C2—C1—C6—C5	−0.6 (4)	C63—O12—C34—C29	172.1 (3)
C35—C1—C6—C5	179.1 (2)	C30—C29—C34—C33	−1.5 (4)
C46—O3—C6—C1	167.2 (2)	C28—C29—C34—C33	176.1 (3)
C46—O3—C6—C5	−15.1 (4)	C30—C29—C34—O12	177.9 (2)
C4—C5—C6—C1	−0.2 (4)	C28—C29—C34—O12	−4.4 (4)
C4—C5—C6—O3	−177.9 (2)	C31—C32—C35—C1	−108.0 (3)
C5—C4—C7—C8	100.6 (3)	C33—C32—C35—C1	69.7 (3)
C3—C4—C7—C8	−79.7 (3)	C6—C1—C35—C32	−96.1 (3)
C4—C7—C8—C9	107.8 (3)	C2—C1—C35—C32	83.6 (3)
C4—C7—C8—C13	−70.8 (3)	C3—O1—C36—C37A	174.3 (8)
C13—C8—C9—C10	1.4 (3)	C3—O1—C36—C37B	171.0 (9)
C7—C8—C9—C10	−177.2 (2)	O1—C36—C37A—N1A	65.5 (19)
C56—O5—C10—C11	−173.5 (2)	O2A—C38A—N1A—C37A	31 (3)
C56—O5—C10—C9	8.8 (4)	N2A—C38A—N1A—C37A	−168.7 (14)
C8—C9—C10—C11	0.6 (4)	C36—C37A—N1A—C38A	129.7 (18)
C8—C9—C10—O5	178.1 (2)	O2A—C38A—N2A—C39A	−13 (2)
O5—C10—C11—C12	−179.6 (2)	N1A—C38A—N2A—C39A	−174.8 (14)
C9—C10—C11—C12	−1.9 (4)	C38A—N2A—C39A—C40A	−169.2 (16)
O5—C10—C11—C14	−1.7 (3)	N2A—C39A—C40A—C45A	−84.5 (9)
C9—C10—C11—C14	176.1 (2)	N2A—C39A—C40A—C41A	111.0 (15)
C10—C11—C12—C13	1.3 (3)	C45A—C40A—C41A—C42A	−3.8 (13)
C14—C11—C12—C13	−176.8 (2)	C39A—C40A—C41A—C42A	158.7 (16)
C11—C12—C13—O6	−178.1 (2)	C40A—C41A—C42A—C43A	0.4 (14)
C11—C12—C13—C8	0.7 (4)	C41A—C42A—C43A—C44A	0.5 (16)
C57—O6—C13—C12	−9.3 (4)	C42A—C43A—C44A—C45A	2.1 (15)
C57—O6—C13—C8	171.9 (2)	C41A—C40A—C45A—C44A	6.4 (13)
C9—C8—C13—C12	−2.1 (3)	C39A—C40A—C45A—C44A	−163.2 (10)
C7—C8—C13—C12	176.6 (2)	C43A—C44A—C45A—C40A	−5.6 (13)
C9—C8—C13—O6	176.8 (2)	O1—C36—C37B—N1B	83.8 (16)
C7—C8—C13—O6	−4.5 (3)	O2B—C38B—N1B—C37B	−10 (4)
C10—C11—C14—C15	−105.6 (3)	N2B—C38B—N1B—C37B	−176.1 (16)
C12—C11—C14—C15	72.4 (3)	C36—C37B—N1B—C38B	150.1 (17)
C11—C14—C15—C16	76.2 (3)	O2B—C38B—N2B—C39B	−7 (3)
C11—C14—C15—C20	−99.3 (3)	N1B—C38B—N2B—C39B	158.9 (13)
C20—C15—C16—C17	0.1 (4)	C38B—N2B—C39B—C40B	131.9 (15)
C14—C15—C16—C17	−175.5 (2)	N2B—C39B—C40B—C41B	117.4 (8)
C58—O7—C17—C18	178.1 (3)	N2B—C39B—C40B—C45B	−60 (2)
C58—O7—C17—C16	−3.0 (4)	C45B—C40B—C41B—C42B	0.0
C15—C16—C17—O7	−180.0 (3)	C39B—C40B—C41B—C42B	−178.7 (11)
C15—C16—C17—C18	−1.2 (4)	C40B—C41B—C42B—C43B	0.0
O7—C17—C18—C19	179.6 (2)	C41B—C42B—C43B—C44B	0.0
C16—C17—C18—C19	0.7 (4)	C42B—C43B—C44B—C45B	0.0
O7—C17—C18—C21	0.0 (4)	C43B—C44B—C45B—C40B	0.0
C16—C17—C18—C21	−179.0 (3)	C41B—C40B—C45B—C44B	0.0
C17—C18—C19—C20	0.8 (4)	C39B—C40B—C45B—C44B	178 (2)
C21—C18—C19—C20	−179.6 (3)	C6—O3—C46—C47A	178.3 (7)
C59—O8—C20—C15	158.8 (3)	C6—O3—C46—C47B	−178.0 (8)
C59—O8—C20—C19	−23.1 (5)	O3—C46—C47A—N3A	−68.7 (10)
C16—C15—C20—O8	179.5 (3)	O4A—C48A—N3A—C47A	9 (3)
C14—C15—C20—O8	−4.9 (4)	N4A—C48A—N3A—C47A	−170.5 (15)
C16—C15—C20—C19	1.4 (4)	C46—C47A—N3A—C48A	−155.8 (13)
C14—C15—C20—C19	176.9 (3)	O4A—C48A—N4A—C49A	−9 (3)
C18—C19—C20—O8	−179.8 (3)	N3A—C48A—N4A—C49A	169.7 (11)
C18—C19—C20—C15	−1.8 (5)	C48A—N4A—C49A—C50A	154.7 (16)
C19—C18—C21—C22	94.6 (3)	N4A—C49A—C50A—C51A	−60.2 (10)
C17—C18—C21—C22	−85.8 (4)	N4A—C49A—C50A—C55A	119.9 (9)
C18—C21—C22—C27	−78.9 (3)	C55A—C50A—C51A—C52A	0.0
C18—C21—C22—C23	99.1 (3)	C49A—C50A—C51A—C52A	−179.9 (8)
C27—C22—C23—C24	1.6 (4)	C50A—C51A—C52A—C53A	0.0
C21—C22—C23—C24	−176.5 (2)	C51A—C52A—C53A—C54A	0.0
C60—O9—C24—C25	−169.5 (3)	C52A—C53A—C54A—C55A	0.0
C60—O9—C24—C23	12.6 (5)	C53A—C54A—C55A—C50A	0.0
C22—C23—C24—C25	−0.1 (4)	C51A—C50A—C55A—C54A	0.0
C22—C23—C24—O9	177.6 (2)	C49A—C50A—C55A—C54A	179.9 (8)
O9—C24—C25—C26	−179.4 (2)	O3—C46—C47B—N3B	−80.3 (11)
C23—C24—C25—C26	−1.5 (4)	O4B—C48B—N3B—C47B	−12 (3)
O9—C24—C25—C28	0.0 (4)	N4B—C48B—N3B—C47B	162 (2)
C23—C24—C25—C28	177.9 (2)	C46—C47B—N3B—C48B	−127.3 (17)
C24—C25—C26—C27	1.7 (4)	O4B—C48B—N4B—C49B	2 (4)
C28—C25—C26—C27	−177.7 (2)	N3B—C48B—N4B—C49B	−172.7 (13)
C23—C22—C27—C26	−1.4 (4)	C48B—N4B—C49B—C50B	−155 (2)
C21—C22—C27—C26	176.7 (2)	N4B—C49B—C50B—C51B	−121.5 (13)
C23—C22—C27—O10	177.7 (2)	N4B—C49B—C50B—C55B	61.1 (15)
C21—C22—C27—O10	−4.2 (4)	C55B—C50B—C51B—C52B	−1.3 (16)
C25—C26—C27—C22	−0.2 (4)	C49B—C50B—C51B—C52B	−178.8 (11)
C25—C26—C27—O10	−179.3 (2)	C50B—C51B—C52B—C53B	1.2 (17)
C61—O10—C27—C22	153.1 (3)	C51B—C52B—C53B—C54B	−3.7 (17)
C61—O10—C27—C26	−27.8 (4)	C52B—C53B—C54B—C55B	6.4 (17)
C24—C25—C28—C29	−89.6 (3)	C51B—C50B—C55B—C54B	3.8 (15)
C26—C25—C28—C29	89.8 (3)	C49B—C50B—C55B—C54B	−178.5 (9)
C25—C28—C29—C30	98.3 (3)	C53B—C54B—C55B—C50B	−6.5 (16)
C25—C28—C29—C34	−79.2 (4)	C65—N5—C66—O13	178.6 (3)
C34—C29—C30—C31	2.0 (4)	C64—N5—C66—O13	−2.5 (5)