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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009003/jq2032sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009003/jq2032Isup3.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989023009003/jq2032Isup4.cdx
Supplementary material

CCDC reference: 2285344

Computing details top

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 top
Crystal data top
C63H70N4O12·C3H7NOF(000) = 2448
Mr = 1148.32Dx = 1.227 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 14.7726 (9) ÅCell parameters from 22911 reflections
b = 16.2952 (11) Åθ = 3.0–25.0°
c = 26.1406 (15) ŵ = 0.09 mm1
β = 98.791 (7)°T = 150 K
V = 6218.7 (7) Å3Block, colorless
Z = 40.20 × 0.18 × 0.11 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5143 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.071
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1717
Tmin = 0.652, Tmax = 0.984k = 1919
48935 measured reflectionsl = 2731
10890 independent reflections
Refinement top
Refinement on F2886 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.157 w = 1/[σ2(Fo2) + (0.0817P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
10890 reflectionsΔρmax = 0.19 e Å3
961 parametersΔρmin = 0.20 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.62562 (11)0.41032 (11)0.50482 (6)0.0734 (5)
O30.64175 (12)0.68117 (12)0.63257 (7)0.0786 (5)
O50.92184 (14)0.26904 (13)0.48061 (7)0.0948 (6)
O60.89860 (13)0.57968 (13)0.56136 (7)0.0863 (6)
O70.91160 (15)0.13445 (14)0.67409 (8)0.1000 (7)
O81.15962 (15)0.37805 (17)0.65071 (9)0.1176 (8)
O90.68083 (17)0.21549 (17)0.79044 (10)0.1156 (8)
O101.02487 (16)0.35280 (19)0.80979 (8)0.1112 (7)
O110.44862 (17)0.41066 (17)0.68237 (9)0.1215 (8)
O120.76036 (16)0.52578 (16)0.80306 (9)0.1159 (8)
O130.74097 (16)0.25255 (15)0.56713 (8)0.1081 (8)
N50.75554 (15)0.33315 (16)0.63726 (9)0.0810 (7)
C10.57978 (16)0.55146 (17)0.60873 (9)0.0639 (7)
C20.57428 (16)0.48341 (16)0.57642 (10)0.0661 (7)
H2A0.5328230.4419130.5806160.079*
C30.62917 (17)0.47575 (16)0.53798 (9)0.0612 (6)
C40.69112 (16)0.53707 (16)0.53078 (9)0.0603 (6)
C50.69554 (17)0.60533 (16)0.56272 (9)0.0660 (7)
H50.7361650.6473810.5582420.079*
C60.64089 (17)0.61253 (16)0.60121 (9)0.0634 (7)
C70.75205 (17)0.53017 (17)0.48923 (9)0.0693 (7)
H7A0.7164700.5082800.4579440.083*
H7B0.7729190.5845200.4813680.083*
C80.83418 (17)0.47580 (17)0.50520 (9)0.0616 (7)
C90.84070 (18)0.39889 (17)0.48388 (9)0.0665 (7)
H90.7944810.3812790.4580080.080*
C100.91391 (19)0.34721 (18)0.49985 (9)0.0660 (7)
C110.98303 (17)0.37151 (18)0.53847 (9)0.0655 (7)
C120.97783 (18)0.44915 (19)0.55917 (9)0.0680 (7)
H121.0244850.4668790.5847580.082*
C130.90563 (19)0.50083 (18)0.54299 (9)0.0656 (7)
C141.06115 (18)0.31531 (19)0.55950 (9)0.0799 (8)
H14A1.1185600.3449090.5615430.096*
H14B1.0630270.2694160.5360530.096*
C151.05064 (17)0.28325 (18)0.61285 (10)0.0693 (7)
C160.98837 (18)0.22190 (18)0.61825 (10)0.0727 (7)
H160.9560620.1978260.5887190.087*
C170.97263 (18)0.19516 (18)0.66647 (11)0.0728 (7)
C181.02084 (19)0.22880 (19)0.71111 (10)0.0732 (8)
C191.08329 (19)0.2895 (2)0.70569 (11)0.0814 (8)
H191.1169300.3124510.7352140.098*
C201.09758 (18)0.31759 (19)0.65755 (11)0.0776 (8)
C211.0057 (2)0.1993 (2)0.76424 (10)0.0915 (9)
H21A0.9937850.1407270.7627250.110*
H21B1.0612010.2082840.7886350.110*
C220.9268 (2)0.2423 (2)0.78379 (10)0.0813 (9)
C230.8408 (2)0.2063 (2)0.77991 (11)0.0893 (9)
H230.8321050.1533600.7667190.107*
C240.7680 (3)0.2478 (2)0.79535 (11)0.0866 (9)
C250.7789 (2)0.3260 (2)0.81507 (10)0.0811 (8)
C260.8647 (2)0.3610 (2)0.82018 (10)0.0871 (9)
H260.8736850.4132700.8343030.105*
C270.9374 (2)0.3198 (2)0.80469 (10)0.0851 (9)
C280.6985 (2)0.3736 (2)0.83055 (10)0.0942 (10)
H28A0.6560900.3354890.8426740.113*
H28B0.7209140.4103200.8589060.113*
C290.6482 (2)0.4234 (2)0.78584 (10)0.0780 (8)
C300.5692 (2)0.3955 (2)0.75650 (12)0.0846 (9)
H300.5435750.3465540.7656200.102*
C310.5268 (2)0.4382 (2)0.71374 (12)0.0811 (8)
C320.56182 (19)0.51127 (19)0.69913 (10)0.0731 (8)
C330.6401 (2)0.5410 (2)0.72939 (12)0.0821 (8)
H330.6643760.5909440.7209230.099*
C340.6826 (2)0.4982 (2)0.77175 (12)0.0835 (9)
C350.51981 (18)0.55673 (19)0.65097 (10)0.0807 (8)
H35A0.5113370.6138770.6594820.097*
H35B0.4600790.5336190.6382980.097*
C360.54778 (18)0.35731 (17)0.50083 (11)0.0768 (8)
H36A0.5468590.3298340.5336600.092*0.549 (9)
H36B0.4921740.3895190.4929930.092*0.549 (9)
H36C0.4911230.3882300.4939380.092*0.451 (9)
H36D0.5481200.3254780.5322110.092*0.451 (9)
C38A0.6146 (11)0.1591 (14)0.4628 (5)0.0720 (19)0.549 (9)
O2A0.5517 (11)0.1335 (13)0.4324 (6)0.097 (3)0.549 (9)
C37A0.5507 (13)0.2980 (14)0.4614 (6)0.076 (2)0.549 (9)
H37A0.5539620.3272520.4294410.091*0.549 (9)
H37B0.4928640.2687070.4567900.091*0.549 (9)
N1A0.6231 (11)0.2377 (11)0.4679 (4)0.071 (2)0.549 (9)
H1A0.6779880.2560620.4760670.086*0.549 (9)
N2A0.6760 (8)0.1091 (8)0.4760 (3)0.0854 (18)0.549 (9)
H2A10.7267360.1284590.4919630.103*0.549 (9)
C39A0.6727 (6)0.0255 (6)0.4680 (4)0.110 (2)0.549 (9)
H39A0.6711040.0140880.4314150.133*0.549 (9)
H39B0.6172320.0035600.4783510.133*0.549 (9)
C40A0.7612 (7)0.0185 (7)0.5009 (4)0.1066 (16)0.549 (9)
C41A0.7884 (7)0.0694 (7)0.5421 (4)0.1199 (18)0.549 (9)
H41A0.7507340.0750980.5672900.144*0.549 (9)
C42A0.8678 (8)0.1116 (7)0.5474 (4)0.129 (2)0.549 (9)
H42A0.8843250.1460340.5756080.155*0.549 (9)
C43A0.9218 (7)0.1032 (7)0.5116 (5)0.128 (2)0.549 (9)
H43A0.9763520.1325490.5149780.153*0.549 (9)
C44A0.8988 (7)0.0517 (7)0.4692 (4)0.137 (2)0.549 (9)
H44A0.9362290.0475140.4437790.164*0.549 (9)
C45A0.8189 (7)0.0069 (7)0.4660 (4)0.125 (2)0.549 (9)
H45A0.8046670.0315520.4397460.150*0.549 (9)
O2B0.5485 (12)0.1386 (16)0.4186 (7)0.083 (3)0.451 (9)
C38B0.6085 (15)0.1585 (18)0.4526 (6)0.075 (2)0.451 (9)
C37B0.5607 (16)0.2987 (17)0.4522 (8)0.078 (3)0.451 (9)
H37C0.5032430.2742140.4365180.094*0.451 (9)
H37D0.5879690.3279710.4260710.094*0.451 (9)
N1B0.6252 (14)0.2360 (13)0.4800 (6)0.080 (2)0.451 (9)
H1B0.6648190.2444810.5071590.095*0.451 (9)
N2B0.6821 (10)0.1073 (10)0.4948 (4)0.093 (2)0.451 (9)
H2B0.7253410.1314860.5150760.112*0.451 (9)
C39B0.6696 (7)0.0226 (7)0.4956 (5)0.108 (2)0.451 (9)
H39C0.6260550.0058150.4658550.130*0.451 (9)
H39D0.6455330.0068360.5266950.130*0.451 (9)
C40B0.7600 (7)0.0189 (8)0.4944 (4)0.1065 (18)0.451 (9)
C41B0.7598 (6)0.0549 (7)0.5426 (4)0.115 (2)0.451 (9)
H41B0.7106590.0466390.5603500.138*0.451 (9)
C42B0.8332 (7)0.1034 (6)0.5642 (3)0.124 (2)0.451 (9)
H42B0.8331680.1275480.5964580.149*0.451 (9)
C43B0.9068 (6)0.1158 (6)0.5377 (5)0.126 (2)0.451 (9)
H43B0.9558770.1482520.5521600.151*0.451 (9)
C44B0.9069 (6)0.0797 (7)0.4895 (5)0.130 (2)0.451 (9)
H44B0.9560760.0880480.4717520.157*0.451 (9)
C45B0.8335 (8)0.0313 (7)0.4679 (3)0.121 (2)0.451 (9)
H45B0.8335670.0071380.4356420.146*0.451 (9)
C460.7154 (2)0.73728 (19)0.63378 (12)0.0901 (9)
H46A0.7177820.7556800.5987220.108*0.525 (6)
H46B0.7721070.7084920.6458000.108*0.525 (6)
H46C0.7162240.7626940.6002990.108*0.475 (6)
H46D0.7740030.7113250.6453810.108*0.475 (6)
O4A0.7106 (11)0.9714 (15)0.6819 (8)0.108 (4)0.525 (6)
C48A0.6429 (11)0.9419 (16)0.6576 (9)0.084 (2)0.525 (6)
C47A0.7103 (10)0.8110 (11)0.6673 (7)0.087 (3)0.525 (6)
H47A0.7007030.7940370.7015950.105*0.525 (6)
H47B0.7672590.8414640.6704130.105*0.525 (6)
N3A0.6335 (13)0.8633 (11)0.6436 (5)0.084 (2)0.525 (6)
H3A0.5872730.8448360.6227870.100*0.525 (6)
N4A0.5565 (11)0.9843 (13)0.6390 (5)0.090 (2)0.525 (6)
H4A0.5145850.9598670.6179570.108*0.525 (6)
C49A0.5415 (5)1.0667 (4)0.6559 (3)0.1006 (17)0.525 (6)
H49A0.5992521.0961440.6607750.121*0.525 (6)
H49B0.5194011.0646600.6889120.121*0.525 (6)
C50A0.4724 (5)1.1128 (5)0.6169 (3)0.1028 (18)0.525 (6)
C51A0.4855 (4)1.1273 (5)0.5661 (3)0.127 (2)0.525 (6)
H51A0.5382371.1084860.5545170.153*0.525 (6)
C52A0.4197 (5)1.1699 (5)0.5326 (2)0.138 (2)0.525 (6)
H52A0.4283961.1795720.4986630.166*0.525 (6)
C53A0.3408 (5)1.1979 (5)0.5499 (3)0.140 (2)0.525 (6)
H53A0.2967651.2264340.5275320.168*0.525 (6)
C54A0.3277 (4)1.1834 (5)0.6007 (3)0.131 (2)0.525 (6)
H54A0.2749741.2022080.6122550.157*0.525 (6)
C55A0.3935 (5)1.1408 (5)0.6341 (2)0.124 (2)0.525 (6)
H55A0.3848141.1311220.6681100.149*0.525 (6)
O4B0.6891 (12)0.9712 (16)0.6886 (8)0.102 (4)0.475 (6)
C48B0.6277 (13)0.9417 (17)0.6589 (10)0.080 (2)0.475 (6)
C47B0.6902 (11)0.7989 (12)0.6736 (7)0.087 (3)0.475 (6)
H47C0.6691080.7686090.7014510.105*0.475 (6)
H47D0.7452090.8282640.6882290.105*0.475 (6)
N3B0.6230 (15)0.8563 (12)0.6544 (6)0.081 (2)0.475 (6)
H3B0.5728330.8366620.6379910.097*0.475 (6)
N4B0.5715 (12)0.9870 (14)0.6288 (6)0.091 (2)0.475 (6)
H4B0.5274260.9635500.6088030.109*0.475 (6)
C49B0.5786 (6)1.0744 (5)0.6271 (4)0.1059 (19)0.475 (6)
H49C0.6221521.0889710.6043430.127*0.475 (6)
H49D0.6023351.0943900.6614300.127*0.475 (6)
C50B0.4904 (7)1.1158 (8)0.6087 (4)0.1045 (18)0.475 (6)
C51B0.4736 (7)1.1659 (6)0.5671 (4)0.116 (2)0.475 (6)
H51B0.5214681.1737360.5482650.140*0.475 (6)
C52B0.3946 (8)1.2055 (7)0.5499 (4)0.127 (2)0.475 (6)
H52B0.3893721.2380080.5203460.152*0.475 (6)
C53B0.3263 (9)1.1979 (8)0.5751 (5)0.135 (2)0.475 (6)
H53B0.2726191.2272870.5650030.161*0.475 (6)
C54B0.3335 (9)1.1457 (8)0.6172 (4)0.135 (2)0.475 (6)
H54B0.2826231.1358200.6333310.162*0.475 (6)
C55B0.4189 (8)1.1070 (7)0.6360 (4)0.122 (2)0.475 (6)
H55B0.4258051.0763000.6663340.146*0.475 (6)
C560.8593 (2)0.2434 (2)0.43776 (13)0.1086 (11)
H56A0.8749830.1891560.4278190.130*
H56B0.8614230.2805060.4094310.130*
H56C0.7986170.2430640.4466850.130*
C570.9618 (2)0.6051 (2)0.60406 (12)0.1104 (11)
H57A0.9481980.6603760.6130920.132*
H57B1.0226190.6028360.5953850.132*
H57C0.9578920.5695300.6329070.132*
C580.8575 (2)0.0987 (2)0.63023 (15)0.1204 (13)
H58A0.8157010.0599060.6414140.144*
H58B0.8966230.0710970.6096040.144*
H58C0.8236310.1408390.6099810.144*
C591.1860 (3)0.4329 (3)0.69066 (18)0.182 (2)
H59A1.1325450.4541350.7029130.218*
H59B1.2194730.4773580.6783260.218*
H59C1.2241180.4054030.7184490.218*
C600.6671 (3)0.1327 (3)0.77892 (18)0.1529 (17)
H60A0.6991760.1002280.8065540.184*
H60B0.6898700.1202320.7473210.184*
H60C0.6028500.1205120.7749420.184*
C611.0326 (3)0.4372 (3)0.8090 (2)0.1614 (19)
H61A1.0954170.4519990.8085730.194*
H61B1.0126380.4597890.8393140.194*
H61C0.9952870.4584650.7786380.194*
C620.4123 (3)0.3358 (3)0.6924 (2)0.189 (2)
H62A0.3620910.3231380.6657270.227*
H62B0.3909050.3377630.7252640.227*
H62C0.4585840.2942670.6932580.227*
C630.8047 (3)0.5954 (3)0.78706 (18)0.1627 (19)
H63A0.7632360.6411790.7838290.195*
H63B0.8238070.5847280.7542200.195*
H63C0.8572720.6080020.8122170.195*
C640.6843 (3)0.2918 (3)0.65897 (15)0.1474 (16)
H64A0.6500130.2575690.6330680.177*
H64B0.6442590.3316350.6707080.177*
H64C0.7111580.2585410.6876440.177*
C650.8021 (3)0.4008 (3)0.66514 (13)0.1316 (14)
H65A0.7593910.4445660.6673690.158*
H65B0.8503030.4196920.6473250.158*
H65C0.8275720.3831740.6993720.158*
C660.7751 (2)0.3092 (2)0.59272 (11)0.0829 (9)
H660.8198470.3388430.5792940.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0728 (12)0.0564 (12)0.0902 (12)0.0020 (10)0.0095 (9)0.0117 (10)
O30.0809 (12)0.0637 (14)0.0912 (12)0.0038 (11)0.0134 (9)0.0192 (10)
O50.1073 (15)0.0850 (17)0.0872 (13)0.0167 (12)0.0007 (11)0.0277 (12)
O60.0845 (13)0.0796 (16)0.0961 (13)0.0122 (11)0.0182 (10)0.0272 (12)
O70.1071 (16)0.0854 (17)0.1028 (15)0.0224 (14)0.0012 (12)0.0122 (12)
O80.1035 (16)0.134 (2)0.1101 (16)0.0527 (16)0.0006 (13)0.0014 (15)
O90.1125 (19)0.097 (2)0.1443 (19)0.0131 (16)0.0409 (14)0.0048 (15)
O100.0924 (17)0.125 (2)0.1089 (16)0.0047 (16)0.0061 (12)0.0237 (15)
O110.1072 (17)0.112 (2)0.1376 (19)0.0312 (16)0.0078 (15)0.0056 (16)
O120.1061 (17)0.109 (2)0.1220 (17)0.0249 (15)0.0149 (14)0.0053 (14)
O130.1306 (19)0.0932 (19)0.0878 (14)0.0077 (14)0.0241 (13)0.0129 (13)
N50.0830 (16)0.094 (2)0.0665 (14)0.0043 (14)0.0121 (12)0.0049 (13)
C10.0585 (15)0.0600 (19)0.0726 (16)0.0112 (14)0.0082 (12)0.0016 (14)
C20.0585 (15)0.0569 (19)0.0819 (17)0.0047 (13)0.0077 (13)0.0061 (14)
C30.0646 (16)0.0464 (18)0.0697 (16)0.0083 (14)0.0011 (12)0.0029 (13)
C40.0658 (16)0.0461 (17)0.0670 (15)0.0062 (14)0.0039 (12)0.0018 (13)
C50.0678 (16)0.0528 (18)0.0760 (16)0.0026 (13)0.0069 (13)0.0041 (14)
C60.0643 (16)0.0532 (19)0.0702 (16)0.0089 (14)0.0024 (13)0.0053 (13)
C70.0819 (18)0.0620 (19)0.0654 (15)0.0013 (15)0.0156 (13)0.0032 (13)
C80.0686 (16)0.066 (2)0.0519 (13)0.0036 (15)0.0159 (12)0.0018 (13)
C90.0747 (18)0.072 (2)0.0534 (14)0.0020 (16)0.0098 (12)0.0107 (14)
C100.0786 (18)0.064 (2)0.0574 (15)0.0018 (16)0.0154 (13)0.0085 (14)
C110.0630 (16)0.081 (2)0.0547 (14)0.0018 (15)0.0160 (12)0.0013 (14)
C120.0653 (17)0.083 (2)0.0568 (15)0.0124 (16)0.0141 (12)0.0117 (15)
C130.0723 (18)0.064 (2)0.0650 (15)0.0089 (16)0.0243 (14)0.0111 (14)
C140.0689 (17)0.099 (2)0.0733 (17)0.0080 (17)0.0156 (13)0.0006 (16)
C150.0577 (16)0.078 (2)0.0706 (17)0.0058 (15)0.0028 (13)0.0011 (14)
C160.0725 (18)0.071 (2)0.0689 (17)0.0034 (16)0.0063 (13)0.0033 (14)
C170.0642 (17)0.063 (2)0.087 (2)0.0017 (15)0.0024 (14)0.0076 (15)
C180.0694 (18)0.074 (2)0.0723 (18)0.0104 (16)0.0012 (14)0.0105 (15)
C190.0767 (19)0.089 (2)0.0717 (18)0.0022 (18)0.0116 (14)0.0010 (16)
C200.0625 (17)0.083 (2)0.083 (2)0.0093 (16)0.0012 (14)0.0014 (16)
C210.098 (2)0.097 (3)0.0741 (18)0.020 (2)0.0046 (16)0.0201 (16)
C220.096 (2)0.086 (3)0.0582 (16)0.011 (2)0.0009 (15)0.0175 (16)
C230.106 (3)0.078 (2)0.084 (2)0.003 (2)0.0143 (18)0.0148 (16)
C240.099 (3)0.085 (3)0.0765 (19)0.004 (2)0.0163 (17)0.0161 (18)
C250.100 (2)0.089 (3)0.0554 (15)0.007 (2)0.0126 (15)0.0134 (16)
C260.103 (2)0.097 (3)0.0582 (16)0.003 (2)0.0017 (15)0.0004 (15)
C270.086 (2)0.103 (3)0.0621 (17)0.004 (2)0.0031 (15)0.0037 (17)
C280.110 (2)0.107 (3)0.0696 (18)0.000 (2)0.0252 (17)0.0061 (17)
C290.085 (2)0.082 (2)0.0719 (18)0.0001 (18)0.0287 (16)0.0066 (16)
C300.086 (2)0.085 (2)0.088 (2)0.0121 (19)0.0284 (17)0.0017 (18)
C310.0705 (19)0.086 (3)0.088 (2)0.0102 (18)0.0167 (16)0.0110 (18)
C320.0691 (18)0.074 (2)0.0799 (18)0.0019 (16)0.0241 (15)0.0043 (16)
C330.0755 (19)0.080 (2)0.093 (2)0.0063 (17)0.0188 (16)0.0029 (17)
C340.077 (2)0.090 (3)0.084 (2)0.0061 (19)0.0125 (16)0.0091 (18)
C350.0725 (17)0.082 (2)0.0904 (19)0.0143 (16)0.0227 (15)0.0012 (16)
C360.0721 (17)0.0569 (19)0.0954 (19)0.0053 (15)0.0062 (14)0.0084 (15)
C38A0.075 (3)0.057 (3)0.077 (4)0.009 (3)0.013 (3)0.010 (4)
O2A0.098 (4)0.069 (4)0.109 (7)0.000 (3)0.027 (5)0.026 (6)
C37A0.075 (4)0.061 (3)0.085 (5)0.011 (3)0.011 (4)0.008 (4)
N1A0.065 (3)0.066 (3)0.074 (4)0.007 (2)0.023 (3)0.013 (4)
N2A0.095 (3)0.062 (3)0.094 (4)0.019 (2)0.003 (4)0.009 (4)
C39A0.121 (3)0.085 (3)0.120 (4)0.010 (3)0.002 (4)0.001 (4)
C40A0.113 (3)0.082 (3)0.124 (3)0.033 (3)0.014 (3)0.013 (3)
C41A0.123 (4)0.095 (4)0.140 (4)0.039 (3)0.013 (3)0.013 (3)
C42A0.124 (5)0.106 (4)0.152 (4)0.043 (4)0.004 (4)0.009 (4)
C43A0.122 (4)0.108 (4)0.145 (5)0.057 (3)0.002 (3)0.011 (4)
C44A0.131 (4)0.117 (5)0.157 (5)0.056 (4)0.008 (4)0.015 (4)
C45A0.122 (4)0.106 (5)0.145 (4)0.042 (3)0.017 (3)0.017 (3)
O2B0.074 (5)0.079 (6)0.092 (7)0.000 (4)0.005 (4)0.028 (5)
C38B0.079 (4)0.062 (3)0.082 (5)0.008 (3)0.010 (4)0.004 (4)
C37B0.078 (5)0.062 (4)0.087 (5)0.012 (4)0.012 (4)0.013 (4)
N1B0.080 (3)0.066 (3)0.084 (6)0.015 (3)0.013 (4)0.011 (4)
N2B0.105 (3)0.062 (3)0.107 (5)0.002 (3)0.000 (4)0.007 (5)
C39B0.118 (4)0.082 (4)0.121 (5)0.016 (3)0.008 (4)0.015 (4)
C40B0.113 (3)0.084 (3)0.122 (4)0.029 (3)0.016 (3)0.010 (3)
C41B0.116 (5)0.096 (4)0.132 (4)0.032 (4)0.016 (4)0.012 (4)
C42B0.120 (5)0.102 (5)0.145 (5)0.028 (4)0.005 (4)0.014 (4)
C43B0.117 (5)0.107 (4)0.150 (5)0.044 (4)0.006 (4)0.015 (4)
C44B0.129 (4)0.110 (5)0.150 (5)0.047 (4)0.011 (4)0.019 (4)
C45B0.121 (4)0.103 (5)0.140 (4)0.046 (4)0.017 (3)0.015 (4)
C460.0774 (19)0.077 (2)0.111 (2)0.0006 (17)0.0009 (16)0.0283 (17)
O4A0.087 (6)0.086 (5)0.141 (7)0.024 (5)0.013 (5)0.009 (5)
C48A0.087 (5)0.067 (3)0.097 (4)0.008 (4)0.010 (4)0.014 (3)
C47A0.079 (5)0.077 (5)0.103 (5)0.002 (4)0.002 (4)0.021 (4)
N3A0.076 (4)0.071 (4)0.099 (5)0.003 (3)0.002 (4)0.016 (4)
N4A0.091 (4)0.066 (3)0.109 (4)0.010 (3)0.004 (3)0.015 (4)
C49A0.111 (4)0.070 (3)0.120 (4)0.005 (3)0.015 (3)0.014 (3)
C50A0.109 (4)0.071 (3)0.130 (4)0.014 (3)0.020 (3)0.005 (3)
C51A0.127 (4)0.110 (5)0.148 (4)0.007 (4)0.029 (3)0.023 (4)
C52A0.148 (5)0.125 (5)0.144 (4)0.005 (4)0.030 (4)0.031 (4)
C53A0.156 (4)0.117 (4)0.148 (4)0.005 (4)0.027 (4)0.028 (4)
C54A0.150 (4)0.104 (4)0.139 (4)0.021 (4)0.026 (4)0.031 (4)
C55A0.136 (4)0.096 (4)0.139 (4)0.021 (4)0.017 (3)0.014 (3)
O4B0.098 (7)0.080 (5)0.119 (6)0.014 (6)0.017 (6)0.033 (5)
C48B0.078 (4)0.064 (3)0.095 (4)0.016 (4)0.006 (4)0.016 (3)
C47B0.081 (5)0.075 (5)0.101 (5)0.006 (4)0.000 (4)0.025 (4)
N3B0.077 (4)0.066 (3)0.098 (5)0.003 (3)0.009 (4)0.019 (4)
N4B0.093 (5)0.066 (3)0.109 (5)0.014 (4)0.000 (4)0.013 (4)
C49B0.112 (4)0.069 (3)0.133 (4)0.015 (3)0.005 (3)0.000 (4)
C50B0.113 (3)0.072 (3)0.128 (4)0.014 (3)0.016 (3)0.005 (3)
C51B0.118 (4)0.091 (5)0.141 (4)0.004 (4)0.024 (3)0.016 (4)
C52B0.129 (4)0.105 (4)0.148 (4)0.006 (4)0.029 (4)0.025 (4)
C53B0.149 (4)0.111 (4)0.146 (5)0.015 (4)0.031 (4)0.019 (4)
C54B0.147 (4)0.111 (5)0.153 (5)0.000 (4)0.041 (4)0.016 (4)
C55B0.139 (4)0.090 (4)0.139 (4)0.004 (4)0.032 (3)0.011 (3)
C560.108 (2)0.101 (3)0.115 (2)0.000 (2)0.010 (2)0.046 (2)
C570.122 (3)0.108 (3)0.103 (2)0.026 (2)0.020 (2)0.045 (2)
C580.111 (3)0.087 (3)0.148 (3)0.029 (2)0.028 (2)0.026 (2)
C590.211 (5)0.168 (5)0.158 (4)0.114 (4)0.001 (3)0.024 (4)
C600.151 (4)0.118 (4)0.199 (5)0.038 (3)0.058 (3)0.011 (3)
C610.112 (3)0.134 (5)0.236 (5)0.029 (3)0.021 (3)0.060 (4)
C620.151 (4)0.156 (5)0.241 (6)0.075 (4)0.027 (4)0.034 (4)
C630.133 (3)0.154 (5)0.187 (4)0.068 (3)0.021 (3)0.030 (3)
C640.151 (3)0.177 (5)0.128 (3)0.022 (3)0.065 (3)0.020 (3)
C650.160 (3)0.136 (4)0.095 (2)0.009 (3)0.007 (2)0.028 (2)
C660.083 (2)0.102 (3)0.0623 (18)0.0095 (19)0.0071 (15)0.0061 (17)
Geometric parameters (Å, º) top
O1—C31.370 (3)C44A—C45A1.379 (11)
O1—C361.429 (3)C44A—H44A0.9300
O3—C61.386 (3)C45A—H45A0.9300
O3—C461.417 (3)O2B—C38B1.2008 (11)
O5—C101.381 (3)C38B—N1B1.45 (4)
O5—C561.402 (3)C38B—N2B1.65 (3)
O6—C131.381 (3)C37B—N1B1.51 (4)
O6—C571.404 (3)C37B—H37C0.9700
O7—C171.373 (3)C37B—H37D0.9700
O7—C581.419 (4)N1B—H1B0.8600
O8—C201.376 (3)N2B—C39B1.394 (16)
O8—C591.385 (4)N2B—H2B0.8600
O9—C241.379 (4)C39B—C40B1.500 (13)
O9—C601.390 (4)C39B—H39C0.9700
O10—C611.380 (5)C39B—H39D0.9700
O10—C271.386 (4)C40B—C41B1.3900
O11—C621.374 (4)C40B—C45B1.3900
O11—C311.385 (3)C41B—C42B1.3900
O12—C341.380 (3)C41B—H41B0.9300
O12—C631.406 (4)C42B—C43B1.3900
O13—C661.204 (3)C42B—H42B0.9300
N5—C661.301 (3)C43B—C44B1.3900
N5—C651.437 (4)C43B—H43B0.9300
N5—C641.437 (4)C44B—C45B1.3900
C1—C61.378 (3)C44B—H44B0.9300
C1—C21.389 (3)C45B—H45B0.9300
C1—C351.520 (3)C46—C47A1.495 (18)
C2—C31.390 (3)C46—C47B1.53 (2)
C2—H2A0.9300C46—H46A0.9700
C3—C41.387 (3)C46—H46B0.9700
C4—C51.386 (3)C46—H46C0.9700
C4—C71.517 (3)C46—H46D0.9700
C5—C61.388 (3)O4A—C48A1.2008 (11)
C5—H50.9300C48A—N3A1.33 (3)
C7—C81.509 (3)C48A—N4A1.47 (3)
C7—H7A0.9700C47A—N3A1.48 (2)
C7—H7B0.9700C47A—H47A0.9700
C8—C91.381 (3)C47A—H47B0.9700
C8—C131.392 (3)N3A—H3A0.8600
C9—C101.384 (3)N4A—C49A1.44 (2)
C9—H90.9300N4A—H4A0.8600
C10—C111.380 (3)C49A—C50A1.526 (8)
C11—C121.383 (4)C49A—H49A0.9700
C11—C141.510 (3)C49A—H49B0.9700
C12—C131.374 (4)C50A—C51A1.3900
C12—H120.9300C50A—C55A1.3900
C14—C151.519 (3)C51A—C52A1.3900
C14—H14A0.9700C51A—H51A0.9300
C14—H14B0.9700C52A—C53A1.3900
C15—C161.380 (4)C52A—H52A0.9300
C15—C201.383 (4)C53A—C54A1.3900
C16—C171.386 (4)C53A—H53A0.9300
C16—H160.9300C54A—C55A1.3900
C17—C181.384 (4)C54A—H54A0.9300
C18—C191.375 (4)C55A—H55A0.9300
C18—C211.518 (4)O4B—C48B1.2008 (11)
C19—C201.385 (4)C48B—N4B1.29 (3)
C19—H190.9300C48B—N3B1.40 (3)
C21—C221.514 (4)C47B—N3B1.40 (2)
C21—H21A0.9700C47B—H47C0.9700
C21—H21B0.9700C47B—H47D0.9700
C22—C271.376 (4)N3B—H3B0.8600
C22—C231.389 (4)N4B—C49B1.43 (2)
C23—C241.383 (4)N4B—H4B0.8600
C23—H230.9300C49B—C50B1.481 (11)
C24—C251.374 (4)C49B—H49C0.9700
C25—C261.378 (4)C49B—H49D0.9700
C25—C281.524 (4)C50B—C51B1.352 (13)
C26—C271.379 (4)C50B—C55B1.370 (8)
C26—H260.9300C51B—C52B1.349 (12)
C28—C291.520 (4)C51B—H51B0.9300
C28—H28A0.9700C52B—C53B1.293 (14)
C28—H28B0.9700C52B—H52B0.9300
C29—C301.372 (4)C53B—C54B1.380 (14)
C29—C341.392 (4)C53B—H53B0.9300
C30—C311.383 (4)C54B—C55B1.429 (14)
C30—H300.9300C54B—H54B0.9300
C31—C321.376 (4)C55B—H55B0.9300
C32—C331.385 (4)C56—H56A0.9600
C32—C351.510 (4)C56—H56B0.9600
C33—C341.376 (4)C56—H56C0.9600
C33—H330.9300C57—H57A0.9600
C35—H35A0.9700C57—H57B0.9600
C35—H35B0.9700C57—H57C0.9600
C36—C37A1.418 (18)C58—H58A0.9600
C36—C37B1.62 (2)C58—H58B0.9600
C36—H36A0.9700C58—H58C0.9600
C36—H36B0.9700C59—H59A0.9600
C36—H36C0.9700C59—H59B0.9600
C36—H36D0.9700C59—H59C0.9600
C38A—O2A1.2011 (10)C60—H60A0.9600
C38A—N2A1.23 (3)C60—H60B0.9600
C38A—N1A1.29 (3)C60—H60C0.9600
C37A—N1A1.44 (3)C61—H61A0.9600
C37A—H37A0.9700C61—H61B0.9600
C37A—H37B0.9700C61—H61C0.9600
N1A—H1A0.8600C62—H62A0.9600
N2A—C39A1.378 (13)C62—H62B0.9600
N2A—H2A10.8600C62—H62C0.9600
C39A—C40A1.619 (12)C63—H63A0.9600
C39A—H39A0.9700C63—H63B0.9600
C39A—H39B0.9700C63—H63C0.9600
C40A—C45A1.354 (7)C64—H64A0.9600
C40A—C41A1.369 (10)C64—H64B0.9600
C41A—C42A1.348 (11)C64—H64C0.9600
C41A—H41A0.9300C65—H65A0.9600
C42A—C43A1.325 (12)C65—H65B0.9600
C42A—H42A0.9300C65—H65C0.9600
C43A—C44A1.391 (11)C66—H660.9300
C43A—H43A0.9300
C3—O1—C36118.0 (2)N1B—C37B—H37C111.9
C6—O3—C46118.1 (2)C36—C37B—H37C111.9
C10—O5—C56118.9 (2)N1B—C37B—H37D111.9
C13—O6—C57118.3 (2)C36—C37B—H37D111.9
C17—O7—C58118.7 (2)H37C—C37B—H37D109.6
C20—O8—C59118.7 (3)C38B—N1B—C37B107.8 (19)
C24—O9—C60119.6 (3)C38B—N1B—H1B126.1
C61—O10—C27117.6 (3)C37B—N1B—H1B126.1
C62—O11—C31119.3 (3)C39B—N2B—C38B115.8 (14)
C34—O12—C63118.0 (3)C39B—N2B—H2B122.1
C66—N5—C65122.0 (3)C38B—N2B—H2B122.1
C66—N5—C64119.2 (3)N2B—C39B—C40B109.0 (11)
C65—N5—C64118.8 (3)N2B—C39B—H39C109.9
C6—C1—C2117.9 (2)C40B—C39B—H39C109.9
C6—C1—C35122.0 (2)N2B—C39B—H39D109.9
C2—C1—C35120.0 (2)C40B—C39B—H39D109.9
C1—C2—C3121.7 (2)H39C—C39B—H39D108.3
C1—C2—H2A119.2C41B—C40B—C45B120.0
C3—C2—H2A119.2C41B—C40B—C39B92.7 (9)
O1—C3—C4115.9 (2)C45B—C40B—C39B147.3 (9)
O1—C3—C2123.9 (2)C42B—C41B—C40B120.0
C4—C3—C2120.2 (2)C42B—C41B—H41B120.0
C5—C4—C3117.9 (2)C40B—C41B—H41B120.0
C5—C4—C7120.8 (2)C43B—C42B—C41B120.0
C3—C4—C7121.3 (2)C43B—C42B—H42B120.0
C4—C5—C6121.7 (2)C41B—C42B—H42B120.0
C4—C5—H5119.2C42B—C43B—C44B120.0
C6—C5—H5119.2C42B—C43B—H43B120.0
C1—C6—O3116.4 (2)C44B—C43B—H43B120.0
C1—C6—C5120.6 (2)C43B—C44B—C45B120.0
O3—C6—C5122.9 (2)C43B—C44B—H44B120.0
C8—C7—C4112.67 (19)C45B—C44B—H44B120.0
C8—C7—H7A109.1C44B—C45B—C40B120.0
C4—C7—H7A109.1C44B—C45B—H45B120.0
C8—C7—H7B109.1C40B—C45B—H45B120.0
C4—C7—H7B109.1O3—C46—C47A115.1 (6)
H7A—C7—H7B107.8O3—C46—C47B100.0 (6)
C9—C8—C13117.4 (2)O3—C46—H46A108.5
C9—C8—C7121.6 (2)C47A—C46—H46A108.5
C13—C8—C7121.0 (2)O3—C46—H46B108.5
C8—C9—C10122.0 (2)C47A—C46—H46B108.5
C8—C9—H9119.0H46A—C46—H46B107.5
C10—C9—H9119.0O3—C46—H46C111.8
C11—C10—O5115.9 (3)C47B—C46—H46C111.8
C11—C10—C9120.2 (2)O3—C46—H46D111.8
O5—C10—C9123.9 (2)C47B—C46—H46D111.8
C10—C11—C12118.0 (3)H46C—C46—H46D109.5
C10—C11—C14122.1 (3)O4A—C48A—N3A125 (2)
C12—C11—C14119.8 (2)O4A—C48A—N4A127 (2)
C13—C12—C11121.8 (2)N3A—C48A—N4A108.3 (15)
C13—C12—H12119.1N3A—C47A—C46108.8 (11)
C11—C12—H12119.1N3A—C47A—H47A109.9
C12—C13—O6124.0 (2)C46—C47A—H47A109.9
C12—C13—C8120.5 (3)N3A—C47A—H47B109.9
O6—C13—C8115.5 (3)C46—C47A—H47B109.9
C11—C14—C15111.3 (2)H47A—C47A—H47B108.3
C11—C14—H14A109.4C48A—N3A—C47A113.5 (15)
C15—C14—H14A109.4C48A—N3A—H3A123.2
C11—C14—H14B109.4C47A—N3A—H3A123.2
C15—C14—H14B109.4C49A—N4A—C48A120.3 (16)
H14A—C14—H14B108.0C49A—N4A—H4A119.9
C16—C15—C20117.6 (2)C48A—N4A—H4A119.9
C16—C15—C14120.4 (2)N4A—C49A—C50A111.9 (8)
C20—C15—C14121.9 (3)N4A—C49A—H49A109.2
C15—C16—C17121.8 (3)C50A—C49A—H49A109.2
C15—C16—H16119.1N4A—C49A—H49B109.2
C17—C16—H16119.1C50A—C49A—H49B109.2
O7—C17—C18115.3 (3)H49A—C49A—H49B107.9
O7—C17—C16124.3 (3)C51A—C50A—C55A120.0
C18—C17—C16120.4 (3)C51A—C50A—C49A123.1 (6)
C19—C18—C17117.7 (3)C55A—C50A—C49A116.9 (6)
C19—C18—C21121.2 (3)C50A—C51A—C52A120.0
C17—C18—C21121.1 (3)C50A—C51A—H51A120.0
C18—C19—C20121.9 (3)C52A—C51A—H51A120.0
C18—C19—H19119.0C51A—C52A—C53A120.0
C20—C19—H19119.0C51A—C52A—H52A120.0
O8—C20—C15116.0 (3)C53A—C52A—H52A120.0
O8—C20—C19123.5 (3)C54A—C53A—C52A120.0
C15—C20—C19120.5 (3)C54A—C53A—H53A120.0
C22—C21—C18113.0 (2)C52A—C53A—H53A120.0
C22—C21—H21A109.0C55A—C54A—C53A120.0
C18—C21—H21A109.0C55A—C54A—H54A120.0
C22—C21—H21B109.0C53A—C54A—H54A120.0
C18—C21—H21B109.0C54A—C55A—C50A120.0
H21A—C21—H21B107.8C54A—C55A—H55A120.0
C27—C22—C23117.7 (3)C50A—C55A—H55A120.0
C27—C22—C21120.8 (3)O4B—C48B—N4B121 (3)
C23—C22—C21121.5 (3)O4B—C48B—N3B118 (2)
C24—C23—C22121.0 (3)N4B—C48B—N3B120.1 (18)
C24—C23—H23119.5N3B—C47B—C46115.3 (12)
C22—C23—H23119.5N3B—C47B—H47C108.4
C25—C24—O9116.3 (3)C46—C47B—H47C108.4
C25—C24—C23120.8 (3)N3B—C47B—H47D108.4
O9—C24—C23122.9 (3)C46—C47B—H47D108.4
C24—C25—C26118.2 (3)H47C—C47B—H47D107.5
C24—C25—C28121.4 (3)C48B—N3B—C47B127.8 (16)
C26—C25—C28120.4 (3)C48B—N3B—H3B116.1
C25—C26—C27121.1 (3)C47B—N3B—H3B116.1
C25—C26—H26119.4C48B—N4B—C49B123.2 (19)
C27—C26—H26119.4C48B—N4B—H4B118.4
C22—C27—C26121.1 (3)C49B—N4B—H4B118.4
C22—C27—O10116.3 (3)N4B—C49B—C50B113.6 (10)
C26—C27—O10122.7 (3)N4B—C49B—H49C108.8
C29—C28—C25112.1 (2)C50B—C49B—H49C108.8
C29—C28—H28A109.2N4B—C49B—H49D108.8
C25—C28—H28A109.2C50B—C49B—H49D108.8
C29—C28—H28B109.2H49C—C49B—H49D107.7
C25—C28—H28B109.2C51B—C50B—C55B114.9 (10)
H28A—C28—H28B107.9C51B—C50B—C49B125.5 (9)
C30—C29—C34117.1 (3)C55B—C50B—C49B119.6 (10)
C30—C29—C28121.8 (3)C52B—C51B—C50B126.9 (10)
C34—C29—C28121.0 (3)C52B—C51B—H51B116.6
C29—C30—C31121.8 (3)C50B—C51B—H51B116.6
C29—C30—H30119.1C53B—C52B—C51B119.1 (11)
C31—C30—H30119.1C53B—C52B—H52B120.4
C32—C31—C30121.1 (3)C51B—C52B—H52B120.4
C32—C31—O11115.5 (3)C52B—C53B—C54B119.7 (12)
C30—C31—O11123.4 (3)C52B—C53B—H53B120.2
C31—C32—C33117.4 (3)C54B—C53B—H53B120.2
C31—C32—C35122.1 (3)C53B—C54B—C55B120.1 (12)
C33—C32—C35120.4 (3)C53B—C54B—H54B119.9
C34—C33—C32121.4 (3)C55B—C54B—H54B119.9
C34—C33—H33119.3C50B—C55B—C54B119.0 (10)
C32—C33—H33119.3C50B—C55B—H55B120.5
C33—C34—O12123.3 (3)C54B—C55B—H55B120.5
C33—C34—C29121.1 (3)O5—C56—H56A109.5
O12—C34—C29115.6 (3)O5—C56—H56B109.5
C32—C35—C1111.5 (2)H56A—C56—H56B109.5
C32—C35—H35A109.3O5—C56—H56C109.5
C1—C35—H35A109.3H56A—C56—H56C109.5
C32—C35—H35B109.3H56B—C56—H56C109.5
C1—C35—H35B109.3O6—C57—H57A109.5
H35A—C35—H35B108.0O6—C57—H57B109.5
C37A—C36—O1110.6 (8)H57A—C57—H57B109.5
O1—C36—C37B102.9 (9)O6—C57—H57C109.5
C37A—C36—H36A109.5H57A—C57—H57C109.5
O1—C36—H36A109.5H57B—C57—H57C109.5
C37A—C36—H36B109.5O7—C58—H58A109.5
O1—C36—H36B109.5O7—C58—H58B109.5
H36A—C36—H36B108.1H58A—C58—H58B109.5
O1—C36—H36C111.2O7—C58—H58C109.5
C37B—C36—H36C111.2H58A—C58—H58C109.5
O1—C36—H36D111.2H58B—C58—H58C109.5
C37B—C36—H36D111.2O8—C59—H59A109.5
H36C—C36—H36D109.1O8—C59—H59B109.5
O2A—C38A—N2A114.7 (19)H59A—C59—H59B109.5
O2A—C38A—N1A117.8 (18)O8—C59—H59C109.5
N2A—C38A—N1A124.9 (16)H59A—C59—H59C109.5
C36—C37A—N1A118.9 (14)H59B—C59—H59C109.5
C36—C37A—H37A107.6O9—C60—H60A109.5
N1A—C37A—H37A107.6O9—C60—H60B109.5
C36—C37A—H37B107.6H60A—C60—H60B109.5
N1A—C37A—H37B107.6O9—C60—H60C109.5
H37A—C37A—H37B107.0H60A—C60—H60C109.5
C38A—N1A—C37A127.2 (18)H60B—C60—H60C109.5
C38A—N1A—H1A116.4O10—C61—H61A109.5
C37A—N1A—H1A116.4O10—C61—H61B109.5
C38A—N2A—C39A127.2 (14)H61A—C61—H61B109.5
C38A—N2A—H2A1116.4O10—C61—H61C109.5
C39A—N2A—H2A1116.4H61A—C61—H61C109.5
N2A—C39A—C40A110.5 (8)H61B—C61—H61C109.5
N2A—C39A—H39A109.6O11—C62—H62A109.5
C40A—C39A—H39A109.6O11—C62—H62B109.5
N2A—C39A—H39B109.6H62A—C62—H62B109.5
C40A—C39A—H39B109.6O11—C62—H62C109.5
H39A—C39A—H39B108.1H62A—C62—H62C109.5
C45A—C40A—C41A118.3 (7)H62B—C62—H62C109.5
C45A—C40A—C39A96.9 (9)O12—C63—H63A109.5
C41A—C40A—C39A143.4 (9)O12—C63—H63B109.5
C42A—C41A—C40A122.4 (8)H63A—C63—H63B109.5
C42A—C41A—H41A118.8O12—C63—H63C109.5
C40A—C41A—H41A118.8H63A—C63—H63C109.5
C43A—C42A—C41A118.9 (9)H63B—C63—H63C109.5
C43A—C42A—H42A120.6N5—C64—H64A109.5
C41A—C42A—H42A120.6N5—C64—H64B109.5
C42A—C43A—C44A121.6 (9)H64A—C64—H64B109.5
C42A—C43A—H43A119.2N5—C64—H64C109.5
C44A—C43A—H43A119.2H64A—C64—H64C109.5
C45A—C44A—C43A118.0 (9)H64B—C64—H64C109.5
C45A—C44A—H44A121.0N5—C65—H65A109.5
C43A—C44A—H44A121.0N5—C65—H65B109.5
C40A—C45A—C44A120.5 (8)H65A—C65—H65B109.5
C40A—C45A—H45A119.8N5—C65—H65C109.5
C44A—C45A—H45A119.8H65A—C65—H65C109.5
O2B—C38B—N1B130 (3)H65B—C65—H65C109.5
O2B—C38B—N2B134 (2)O13—C66—N5126.6 (3)
N1B—C38B—N2B93.7 (13)O13—C66—H66116.7
N1B—C37B—C3699.4 (15)N5—C66—H66116.7
C6—C1—C2—C30.9 (4)C28—C29—C30—C31175.7 (3)
C35—C1—C2—C3178.8 (2)C29—C30—C31—C320.6 (4)
C36—O1—C3—C4163.3 (2)C29—C30—C31—O11178.0 (3)
C36—O1—C3—C215.7 (3)C62—O11—C31—C32176.1 (4)
C1—C2—C3—O1179.3 (2)C62—O11—C31—C302.6 (5)
C1—C2—C3—C40.4 (4)C30—C31—C32—C331.2 (4)
O1—C3—C4—C5178.6 (2)O11—C31—C32—C33179.9 (2)
C2—C3—C4—C50.4 (3)C30—C31—C32—C35176.6 (3)
O1—C3—C4—C71.2 (3)O11—C31—C32—C352.2 (4)
C2—C3—C4—C7179.8 (2)C31—C32—C33—C341.6 (4)
C3—C4—C5—C60.7 (4)C35—C32—C33—C34176.2 (3)
C7—C4—C5—C6179.5 (2)C32—C33—C34—O12179.7 (3)
C2—C1—C6—O3177.2 (2)C32—C33—C34—C290.2 (4)
C35—C1—C6—O33.1 (3)C63—O12—C34—C338.4 (5)
C2—C1—C6—C50.6 (4)C63—O12—C34—C29172.1 (3)
C35—C1—C6—C5179.1 (2)C30—C29—C34—C331.5 (4)
C46—O3—C6—C1167.2 (2)C28—C29—C34—C33176.1 (3)
C46—O3—C6—C515.1 (4)C30—C29—C34—O12177.9 (2)
C4—C5—C6—C10.2 (4)C28—C29—C34—O124.4 (4)
C4—C5—C6—O3177.9 (2)C31—C32—C35—C1108.0 (3)
C5—C4—C7—C8100.6 (3)C33—C32—C35—C169.7 (3)
C3—C4—C7—C879.7 (3)C6—C1—C35—C3296.1 (3)
C4—C7—C8—C9107.8 (3)C2—C1—C35—C3283.6 (3)
C4—C7—C8—C1370.8 (3)C3—O1—C36—C37A174.3 (8)
C13—C8—C9—C101.4 (3)C3—O1—C36—C37B171.0 (9)
C7—C8—C9—C10177.2 (2)O1—C36—C37A—N1A65.5 (19)
C56—O5—C10—C11173.5 (2)O2A—C38A—N1A—C37A31 (3)
C56—O5—C10—C98.8 (4)N2A—C38A—N1A—C37A168.7 (14)
C8—C9—C10—C110.6 (4)C36—C37A—N1A—C38A129.7 (18)
C8—C9—C10—O5178.1 (2)O2A—C38A—N2A—C39A13 (2)
O5—C10—C11—C12179.6 (2)N1A—C38A—N2A—C39A174.8 (14)
C9—C10—C11—C121.9 (4)C38A—N2A—C39A—C40A169.2 (16)
O5—C10—C11—C141.7 (3)N2A—C39A—C40A—C45A84.5 (9)
C9—C10—C11—C14176.1 (2)N2A—C39A—C40A—C41A111.0 (15)
C10—C11—C12—C131.3 (3)C45A—C40A—C41A—C42A3.8 (13)
C14—C11—C12—C13176.8 (2)C39A—C40A—C41A—C42A158.7 (16)
C11—C12—C13—O6178.1 (2)C40A—C41A—C42A—C43A0.4 (14)
C11—C12—C13—C80.7 (4)C41A—C42A—C43A—C44A0.5 (16)
C57—O6—C13—C129.3 (4)C42A—C43A—C44A—C45A2.1 (15)
C57—O6—C13—C8171.9 (2)C41A—C40A—C45A—C44A6.4 (13)
C9—C8—C13—C122.1 (3)C39A—C40A—C45A—C44A163.2 (10)
C7—C8—C13—C12176.6 (2)C43A—C44A—C45A—C40A5.6 (13)
C9—C8—C13—O6176.8 (2)O1—C36—C37B—N1B83.8 (16)
C7—C8—C13—O64.5 (3)O2B—C38B—N1B—C37B10 (4)
C10—C11—C14—C15105.6 (3)N2B—C38B—N1B—C37B176.1 (16)
C12—C11—C14—C1572.4 (3)C36—C37B—N1B—C38B150.1 (17)
C11—C14—C15—C1676.2 (3)O2B—C38B—N2B—C39B7 (3)
C11—C14—C15—C2099.3 (3)N1B—C38B—N2B—C39B158.9 (13)
C20—C15—C16—C170.1 (4)C38B—N2B—C39B—C40B131.9 (15)
C14—C15—C16—C17175.5 (2)N2B—C39B—C40B—C41B117.4 (8)
C58—O7—C17—C18178.1 (3)N2B—C39B—C40B—C45B60 (2)
C58—O7—C17—C163.0 (4)C45B—C40B—C41B—C42B0.0
C15—C16—C17—O7180.0 (3)C39B—C40B—C41B—C42B178.7 (11)
C15—C16—C17—C181.2 (4)C40B—C41B—C42B—C43B0.0
O7—C17—C18—C19179.6 (2)C41B—C42B—C43B—C44B0.0
C16—C17—C18—C190.7 (4)C42B—C43B—C44B—C45B0.0
O7—C17—C18—C210.0 (4)C43B—C44B—C45B—C40B0.0
C16—C17—C18—C21179.0 (3)C41B—C40B—C45B—C44B0.0
C17—C18—C19—C200.8 (4)C39B—C40B—C45B—C44B178 (2)
C21—C18—C19—C20179.6 (3)C6—O3—C46—C47A178.3 (7)
C59—O8—C20—C15158.8 (3)C6—O3—C46—C47B178.0 (8)
C59—O8—C20—C1923.1 (5)O3—C46—C47A—N3A68.7 (10)
C16—C15—C20—O8179.5 (3)O4A—C48A—N3A—C47A9 (3)
C14—C15—C20—O84.9 (4)N4A—C48A—N3A—C47A170.5 (15)
C16—C15—C20—C191.4 (4)C46—C47A—N3A—C48A155.8 (13)
C14—C15—C20—C19176.9 (3)O4A—C48A—N4A—C49A9 (3)
C18—C19—C20—O8179.8 (3)N3A—C48A—N4A—C49A169.7 (11)
C18—C19—C20—C151.8 (5)C48A—N4A—C49A—C50A154.7 (16)
C19—C18—C21—C2294.6 (3)N4A—C49A—C50A—C51A60.2 (10)
C17—C18—C21—C2285.8 (4)N4A—C49A—C50A—C55A119.9 (9)
C18—C21—C22—C2778.9 (3)C55A—C50A—C51A—C52A0.0
C18—C21—C22—C2399.1 (3)C49A—C50A—C51A—C52A179.9 (8)
C27—C22—C23—C241.6 (4)C50A—C51A—C52A—C53A0.0
C21—C22—C23—C24176.5 (2)C51A—C52A—C53A—C54A0.0
C60—O9—C24—C25169.5 (3)C52A—C53A—C54A—C55A0.0
C60—O9—C24—C2312.6 (5)C53A—C54A—C55A—C50A0.0
C22—C23—C24—C250.1 (4)C51A—C50A—C55A—C54A0.0
C22—C23—C24—O9177.6 (2)C49A—C50A—C55A—C54A179.9 (8)
O9—C24—C25—C26179.4 (2)O3—C46—C47B—N3B80.3 (11)
C23—C24—C25—C261.5 (4)O4B—C48B—N3B—C47B12 (3)
O9—C24—C25—C280.0 (4)N4B—C48B—N3B—C47B162 (2)
C23—C24—C25—C28177.9 (2)C46—C47B—N3B—C48B127.3 (17)
C24—C25—C26—C271.7 (4)O4B—C48B—N4B—C49B2 (4)
C28—C25—C26—C27177.7 (2)N3B—C48B—N4B—C49B172.7 (13)
C23—C22—C27—C261.4 (4)C48B—N4B—C49B—C50B155 (2)
C21—C22—C27—C26176.7 (2)N4B—C49B—C50B—C51B121.5 (13)
C23—C22—C27—O10177.7 (2)N4B—C49B—C50B—C55B61.1 (15)
C21—C22—C27—O104.2 (4)C55B—C50B—C51B—C52B1.3 (16)
C25—C26—C27—C220.2 (4)C49B—C50B—C51B—C52B178.8 (11)
C25—C26—C27—O10179.3 (2)C50B—C51B—C52B—C53B1.2 (17)
C61—O10—C27—C22153.1 (3)C51B—C52B—C53B—C54B3.7 (17)
C61—O10—C27—C2627.8 (4)C52B—C53B—C54B—C55B6.4 (17)
C24—C25—C28—C2989.6 (3)C51B—C50B—C55B—C54B3.8 (15)
C26—C25—C28—C2989.8 (3)C49B—C50B—C55B—C54B178.5 (9)
C25—C28—C29—C3098.3 (3)C53B—C54B—C55B—C50B6.5 (16)
C25—C28—C29—C3479.2 (4)C65—N5—C66—O13178.6 (3)
C34—C29—C30—C312.0 (4)C64—N5—C66—O132.5 (5)
Intermolecular interactions(Å, °) between the pillararene host and the DMF guest top
π2 and π5 are the centroids of the C8–C13 and C29–C34 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O130.862.422.905 (12)116
C66—H66···π20.9302.5593.464165
C64—H64B···π50.9603.0253.898152
Intermolecular interactions (Å,°) engaged by DUP in the crystal network top
π1, π3 and π7 are the centroids of the C1–C6, C15–C20 and C51A–C55A phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O2Ai0.862.353.13 (2)151
N4A—H4A···O2Ai0.862.152.97 (2)159
C36—H36B···π1i0.972.543.427 (3)152
C39A—H39B···π7i0.973.043.374 (10)105
C43A—H43A···O5ii0.932.683.54 (1)155
C58—H58A···O4Aiii0.962.473.43 (2)172
C63—H63C···π3iv0.962.913.638 (5)133
Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 2 - x, -y, 1 - z; (iii) x, -1 + y, z; (iv) 2 - x, 1/2 + y, 3/2 - z.
 

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