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Two single-crystal X-ray diffraction data sets of cyclosporine A were measured to high resolution using synchrotron radiation at temperatures of 5 and 90 K. They allowed an accurate determination of its molecular and electronic structure. Three electron-density models based on pseudo­atom scattering factors were compared in terms of derived bond topological properties and in terms of electron-density differences on a grid. In one model multipole parameters were freely refined, whereas in the other two models the density was built up from fixed database parameters from the invariom database and University at Buffalo Databank. The data quality not only allowed benchmarking of the quality of both databases with the refined density, but also judgement of the feasibility of a multipole refinement of a larger oligo­peptide structure such as cyclosporine A. Both databases performed equally well and reproduced the experimentally determined charge density satisfactorily.

Supporting information

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0907444908040602/dz5137sup3.pdf
Supplementary material

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0907444908040602/dz5137sup1.cif
Contains datablock CYCLO

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0907444908040602/dz5137CYCLOsup2.hkl
Contains datablock CYCLO

CCDC reference: 725429

Computing details top

Program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

(E)-14,17,26,32-tetrabutyl-5-ethyl-8-(1-hydroxy-2-methylhex-4-enyl)- 1,3,9,12,15,18,20,23,27-nonamethyl-11,29-dipropyl- 1,3,6,9,12,15,18,21,24,27,30-undecaazacyclodotriacontan- 2,4,7,10,13,16,19,22,25,28,31-undecaone top
Crystal data top
C62H111N11O12·0.754(H2O)Dx = 1.159 Mg m3
Mr = 1216.21Melting point: 150 K
Orthorhombic, P212121Monochromated synchrotron radiation radiation, λ = 0.6261 Å
Hall symbol: P 2ac 2abCell parameters from 19564 reflections
a = 12.4960 (15) Åθ = 10–34.7°
b = 15.6450 (14) ŵ = 0.81 mm1
c = 35.653 (3) ÅT = 5 K
V = 6970.2 (12) Å3Rectangle, colorless
Z = 40.5 × 0.3 × 0.3 mm
F(000) = 2654.2
Data collection top
Diffractometer X10SA beamline at the SLSRint = 0.008
Radiation source: Synchrotronθmax = 34.7°
φ scansh = 2222
246948 measured reflectionsk = 026
40848 independent reflectionsl = 063
40377 reflections with F2 > 3σ F2
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025 w2 = 1/[s2(Fo2)]
wR(F2) = 0.057(Δ/σ)max < 0.001
S = 3.70Δρmax = 0.26 e Å3
40377 reflectionsΔρmin = 0.25 e Å3
1279 parameters
Special details top

Experimental. A helium gas-flow low temperature device was used.

Refinement. A rotationally disordered methyl group was modeled with an alternative position for all three hydrogen atoms. Friedel pairs were not merged, as the molecule is chiral and the accuracy of the measurement (Rint = 0.8%) suggested that anomalous dispersion might otherwise cause a small effect.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O(10)0.71584 (3)0.45769 (2)0.159103 (9)0.015
O(20)0.46835 (3)0.33545 (2)0.210138 (10)0.015
O(30)0.47100 (3)0.31127 (2)0.082536 (9)0.015
O(40)0.57974 (3)0.04789 (2)0.083755 (9)0.014
O(50)0.50842 (3)0.00420 (2)0.039859 (9)0.017
O(60)0.72506 (3)0.21223 (3)0.022315 (9)0.018
O(70)0.51275 (3)0.18019 (2)0.081466 (9)0.015
O(80)0.85154 (3)0.14240 (2)0.136386 (10)0.018
O(83)0.13203 (4)0.12882 (3)0.15930 (2)0.0160.7535
O(90)0.70443 (3)0.12044 (2)0.158550 (9)0.014
O(100)0.98466 (3)0.21649 (2)0.214158 (9)0.014
O(112)0.78463 (9)0.47479 (7)0.29324 (6)0.028
O(82)0.98512 (4)0.09172 (4)0.098737 (16)0.017
N(1)0.66662 (4)0.49925 (2)0.217935 (13)0.013
N(2)0.49587 (3)0.39590 (3)0.153107 (11)0.013
N(3)0.52331 (3)0.22102 (3)0.128792 (10)0.011
N(4)0.55815 (3)0.15633 (3)0.042278 (10)0.012
N(5)0.50350 (3)0.05472 (3)0.019874 (11)0.012
N(6)0.56012 (3)0.21472 (3)0.004558 (10)0.013
N(7)0.63821 (3)0.28292 (3)0.086176 (11)0.014
N(8)0.68459 (3)0.09033 (3)0.124308 (10)0.013
N(9)0.85700 (3)0.04122 (3)0.160384 (13)0.013
N(10)0.80291 (3)0.21968 (3)0.216361 (9)0.011
N(11)0.86538 (3)0.38341 (3)0.254319 (13)0.011
C(10)0.64513 (3)0.47638 (3)0.181699 (11)0.012
C(11)0.52775 (3)0.47818 (3)0.168235 (12)0.014
C(12)0.51840 (4)0.54566 (3)0.137448 (15)0.022
C(20)0.46899 (3)0.32994 (3)0.175737 (11)0.011
C(21)0.43857 (3)0.24726 (3)0.154615 (11)0.011
C(22)0.41280 (3)0.17486 (3)0.181477 (12)0.016
C(30)0.53030 (3)0.25354 (3)0.093978 (10)0.011
C(31)0.61554 (3)0.21390 (3)0.068453 (10)0.011
C(32)0.68019 (3)0.28506 (3)0.049891 (11)0.014
C(33)0.74094 (3)0.33789 (3)0.079485 (11)0.014
C(34)0.83741 (4)0.28963 (4)0.095300 (16)0.024
C(35)0.77454 (4)0.42377 (3)0.063075 (14)0.02
C(40)0.53671 (3)0.07668 (3)0.055106 (10)0.011
C(41)0.45293 (3)0.02149 (3)0.034963 (11)0.012
C(42)0.36347 (3)0.00011 (3)0.063244 (13)0.016
C(43)0.28185 (4)0.06076 (4)0.045810 (16)0.022
C(44)0.30894 (4)0.08230 (4)0.076526 (15)0.022
C(50)0.52752 (3)0.06097 (3)0.017065 (11)0.012
C(51)0.58811 (3)0.14227 (3)0.028767 (10)0.012
C(52)0.57661 (3)0.16320 (3)0.070463 (11)0.015
C(53)0.66077 (4)0.22789 (3)0.083662 (12)0.017
C(54)0.63000 (5)0.26572 (4)0.121691 (13)0.024
C(55)0.77243 (4)0.18782 (4)0.085714 (13)0.025
C(60)0.63397 (3)0.24200 (3)0.020608 (11)0.013
C(61)0.60256 (4)0.31108 (4)0.048982 (14)0.015
C(70)0.58864 (3)0.21188 (3)0.099053 (11)0.013
C(71)0.62660 (3)0.16760 (3)0.135102 (11)0.014
C(72)0.53095 (4)0.14225 (4)0.159740 (12)0.018
C(73)0.46817 (4)0.21852 (4)0.174821 (14)0.025
C(80)0.79182 (3)0.08296 (3)0.127391 (10)0.012
C(81)0.83493 (3)0.00821 (3)0.122307 (10)0.011
C(82)0.93361 (3)0.01112 (3)0.096541 (12)0.012
C(83)0.90050 (3)0.00582 (3)0.055479 (11)0.014
C(84)0.99937 (4)0.02497 (4)0.031706 (13)0.02
C(85)0.83840 (3)0.07067 (3)0.039014 (11)0.015
C(86)0.78517 (4)0.05137 (4)0.002412 (15)0.017
C(87)0.80823 (5)0.09019 (5)0.029835 (16)0.021
C(88)0.75411 (5)0.07418 (5)0.066681 (13)0.027
C(90)0.78429 (3)0.09502 (3)0.175743 (12)0.011
C(91)0.80054 (3)0.12539 (3)0.216315 (10)0.011
C(92)0.71360 (3)0.08651 (3)0.241846 (11)0.012
C(93)0.72558 (4)0.11886 (3)0.282125 (12)0.017
C(94)0.72085 (3)0.01135 (3)0.240461 (12)0.015
C(100)0.90038 (3)0.25782 (3)0.215157 (10)0.01
C(101)0.90243 (3)0.35677 (3)0.216712 (10)0.01
C(1E)1.01516 (3)0.39128 (3)0.208961 (10)0.011
C(1F)1.05531 (3)0.37922 (3)0.168479 (10)0.012
C(1G)1.17765 (3)0.37478 (4)0.167837 (12)0.019
C(1H)1.01475 (3)0.45108 (3)0.142930 (11)0.015
C(110)0.80936 (11)0.45521 (13)0.26114 (6)0.015
C(111)0.77855 (4)0.51478 (3)0.228948 (13)0.011
C(1I)0.79521 (3)0.60766 (3)0.240856 (11)0.012
C(1J)0.79179 (3)0.67188 (3)0.208441 (11)0.012
C(1K)0.77918 (4)0.76220 (3)0.224407 (12)0.016
C(1L)0.89301 (4)0.66501 (3)0.184305 (12)0.016
C(19)0.58265 (4)0.51434 (4)0.245851 (13)0.02
C(49)0.51246 (5)0.19114 (3)0.007706 (13)0.021
C(69)0.44913 (3)0.24466 (3)0.005451 (13)0.017
C(79)0.73965 (4)0.31743 (3)0.100163 (13)0.017
C(99)0.94614 (12)0.00409 (9)0.18099 (3)0.025
C(98)0.70301 (3)0.26801 (3)0.212472 (12)0.013
C(97)0.90127 (3)0.33210 (3)0.286270 (11)0.014
H(83A)0.1613740.0808240.1729440.043 (5)0.7535
H(83B)0.0941470.1657240.1765310.053 (5)0.7535
H(82A)1.0264960.0950240.1215440.049 (6)
H(2)0.4937640.3875780.1250520.038 (3)
H(3)0.5779370.1775890.1372250.042 (3)
H(5)0.5211130.1039070.0371080.031 (3)
H(8)0.6426750.0403390.1141180.039 (3)
H(11)0.4750820.4954780.1917270.034 (2)
H(12A)0.5427940.605930.1479250.052 (2)
H(12B)0.4380170.5494220.1281860.062 (3)
H(12C)0.568140.5283560.114630.053 (3)
H(21)0.366240.2606780.1380950.037 (2)
H(22A)0.3840140.1215660.1661960.044 (2)
H(22B)0.3534490.1953020.2006890.062 (3)
H(22C)0.4829310.1573390.1962750.060 (3)
H(31)0.6699220.175330.0857870.023 (2)
H(32A)0.6263820.326830.034190.041 (2)
H(32B)0.7373230.2569620.0302690.056 (3)
H(33)0.6855850.3506230.1027760.038 (3)
H(34A)0.8741840.3268640.1164950.041 (2)
H(34B)0.8933090.2777450.0735920.062 (3)
H(34C)0.8116090.2307490.1068270.056 (3)
H(35A)0.8276790.413720.0403590.060 (3)
H(35B)0.8134270.4605720.0839490.051 (2)
H(35C)0.7059440.4571140.0535820.049 (2)
H(41)0.4181840.0587030.011830.029 (2)
H(42)0.3996320.0319510.0876230.033 (2)
H(43A)0.3185020.1204170.0401570.067 (3)
H(43B)0.2526630.0340550.0205060.054 (3)
H(43C)0.2171590.0699320.0645710.057 (3)
H(44A)0.2478380.0672560.0960220.050 (2)
H(44B)0.2748590.1142380.0532190.058 (3)
H(44C)0.3662780.1226770.0893490.052 (2)
H(51)0.6734130.129170.0239490.034 (2)
H(52A)0.4968760.1892190.0756480.045 (3)
H(52B)0.5847520.1044780.0867710.038 (2)
H(53)0.6635520.2803530.0631870.039 (3)
H(54A)0.6266920.216250.1419350.044 (2)
H(54B)0.5539210.2951940.11970.051 (2)
H(54C)0.687520.3117780.129890.066 (3)
H(55A)0.8293130.235560.0924820.067 (3)
H(55B)0.7920240.1600370.0595130.061 (3)
H(55C)0.7731070.1398620.1066770.054 (3)
H(61A)0.5159310.3202470.0487450.020 (3)
H(61B)0.6404760.3716990.0416460.033 (3)
H(71)0.6797850.2106870.1507650.023 (2)
H(72A)0.5599830.1040890.1832820.040 (2)
H(72B)0.4770140.1019380.1433730.051 (3)
H(73A)0.436550.254290.1521720.049 (2)
H(73B)0.4047070.1966830.1920170.074 (3)
H(73C)0.519870.2580690.1907170.049 (2)
H(81)0.7714430.0474050.1096860.031 (2)
H(82)0.9902090.038870.1052340.026 (3)
H(83)0.8480010.0621620.0548880.035 (3)
H(84A)1.0381020.0802970.0421220.046 (2)
H(84B)1.0526830.0275790.0329220.049 (2)
H(84C)0.9759250.0354790.0035380.053 (3)
H(85A)0.7773720.0906860.0591010.039 (2)
H(85B)0.8937520.1239630.0351660.052 (3)
H(86)0.7238730.0029890.0019160.046 (6)
H(87)0.8716960.136760.0293610.062 (6)
H(88A)0.8111050.0522560.0864460.073 (3)
H(88B)0.7195790.1319020.0763870.074 (3)
H(88C)0.6932930.0276710.0633010.064 (3)
H(91)0.8787960.1020580.2259630.028 (2)
H(92)0.6347240.1060840.2312610.029 (2)
H(93A)0.715120.1860130.282770.045 (2)
H(93B)0.8028220.1031790.2922270.052 (2)
H(93C)0.6670580.0893470.2992670.048 (2)
H(94A)0.6612430.0381610.2579940.043 (2)
H(94B)0.7973420.0311320.2498470.043 (2)
H(94C)0.708920.032670.2125820.048 (2)
H(101)0.8471020.3820760.1954780.0223 (19)
H(11E)1.0712240.3596120.2279050.035 (2)
H(12E)1.0162310.459450.2155190.034 (2)
H(1F)1.0239240.3182560.1578240.034 (2)
H(11G)1.2044440.3644720.1400230.052 (2)
H(12G)1.203840.3239010.1851440.057 (3)
H(13G)1.2094850.433130.1779420.055 (3)
H(11H)1.050340.5096520.1510580.037 (2)
H(12H)0.9305010.455950.1453310.048 (2)
H(13H)1.0355170.4372530.1147790.048 (2)
H(111)0.8264690.5020110.2071960.028 (4)
H(11I)0.8726070.612980.2548820.037 (2)
H(12I)0.7332510.6246930.2611220.033 (2)
H(1J)0.7217940.6575480.1908710.031 (2)
H(11K)0.7031590.7681010.2372770.059 (3)
H(12K)0.7857290.8074980.2024560.042 (2)
H(13K)0.8399990.7736520.2444720.050 (2)
H(11L)0.8951130.7163240.1649490.049 (2)
H(12L)0.8925380.6061950.1696020.047 (2)
H(13L)0.9616120.6678850.2016990.035 (2)
H(19A)0.5417870.5723990.2395390.040 (2)
H(19B)0.6178140.5191510.273010.048 (3)
H(19C)0.5267510.4628710.2455550.038 (2)
H(49A)0.506530.141640.0127370.035 (2)
H(49B)0.5626070.2408430.0027490.069 (3)
H(49C)0.4346880.2162160.0131710.056 (3)
H(69A)0.4468940.3093820.0147670.053 (3)
H(69B)0.4035050.2058990.0241290.039 (2)
H(69C)0.4153610.2407960.0219530.048 (3)
H(79A)0.7917350.3302250.0771590.078 (6)0.7172
H(79B)0.7246170.3752740.1150610.050 (5)0.7172
H(79C)0.776070.2720840.1184680.058 (5)0.7172
H(79D)0.7365340.3216290.1299860.092 (18)0.2828
H(79E)0.7983580.279760.0927350.10 (2)0.2828
H(79F)0.7521060.3796050.0887370.092 (18)0.2828
H(99A)0.977760.0446960.2022840.078 (4)
H(99B)1.0010170.0304070.1638140.058 (4)
H(99C)0.9082320.0455570.196570.060 (4)
H(98A)0.6984570.3152420.2339620.048 (3)
H(98B)0.636540.2256510.2148640.042 (2)
H(98C)0.7010450.2986820.1857820.053 (3)
H(97A)0.8916660.3678680.3114950.041 (2)
H(97B)0.983470.3156970.282780.049 (3)
H(97C)0.8548530.2750550.2878970.045 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(10)0.01254 (11)0.02118 (17)0.01157 (11)0.00190 (10)0.00115 (9)0.00154 (11)
O(20)0.01604 (13)0.01693 (17)0.01332 (12)0.00025 (11)0.00172 (8)0.00133 (10)
O(30)0.01504 (12)0.01702 (15)0.01305 (12)0.00437 (11)0.00160 (9)0.00261 (11)
O(40)0.01471 (12)0.01369 (15)0.01439 (11)0.00038 (10)0.00338 (9)0.00135 (10)
O(50)0.01850 (14)0.01901 (16)0.01439 (12)0.00582 (12)0.00068 (9)0.00212 (12)
O(60)0.01039 (12)0.02656 (18)0.01746 (13)0.00020 (11)0.00166 (9)0.00645 (13)
O(70)0.01387 (11)0.01545 (15)0.01467 (11)0.00016 (10)0.00092 (9)0.00102 (11)
O(80)0.01476 (13)0.01377 (16)0.02580 (16)0.00193 (11)0.00160 (10)0.00419 (12)
O(83)0.0153 (2)0.0194 (3)0.0137 (3)0.0002 (2)0.00076 (12)0.00039 (15)
O(90)0.01137 (11)0.01607 (15)0.01418 (11)0.00442 (10)0.00316 (9)0.00150 (11)
O(100)0.00893 (11)0.01273 (15)0.02141 (14)0.00135 (10)0.00047 (8)0.00243 (11)
O(112)0.0395 (4)0.0294 (3)0.0158 (3)0.0168 (3)0.00907 (18)0.0058 (2)
O(82)0.01723 (16)0.0175 (2)0.01523 (17)0.00676 (16)0.00294 (14)0.00289 (16)
N(1)0.01299 (16)0.0124 (2)0.01266 (16)0.00103 (11)0.00289 (12)0.00336 (12)
N(2)0.01428 (13)0.01134 (17)0.01399 (14)0.00160 (11)0.00119 (9)0.00042 (12)
N(3)0.01011 (11)0.01099 (15)0.01056 (12)0.00151 (10)0.00019 (9)0.00134 (10)
N(4)0.01447 (13)0.01223 (17)0.01056 (12)0.00103 (11)0.00250 (9)0.00039 (11)
N(5)0.01258 (12)0.01254 (17)0.01204 (13)0.00132 (11)0.00038 (9)0.00141 (12)
N(6)0.01056 (12)0.01394 (16)0.01311 (12)0.00005 (11)0.00123 (9)0.00104 (12)
N(7)0.01599 (13)0.01306 (17)0.01334 (13)0.00007 (12)0.00120 (10)0.00041 (12)
N(8)0.01132 (13)0.01230 (17)0.01566 (14)0.00157 (11)0.00101 (9)0.00187 (12)
N(9)0.01139 (14)0.01369 (18)0.01277 (15)0.00366 (14)0.00305 (11)0.00326 (14)
N(10)0.00852 (12)0.00869 (16)0.01438 (13)0.00018 (10)0.00096 (8)0.00022 (10)
N(11)0.01203 (13)0.01057 (18)0.00989 (16)0.00076 (14)0.00026 (9)0.00091 (13)
C(10)0.01143 (13)0.01109 (17)0.01274 (14)0.00078 (11)0.00125 (10)0.00102 (12)
C(11)0.01188 (13)0.01110 (18)0.01933 (16)0.00069 (12)0.00015 (11)0.00160 (13)
C(12)0.02014 (19)0.0140 (2)0.0311 (2)0.00010 (15)0.00694 (15)0.00550 (17)
C(20)0.01001 (12)0.01202 (18)0.01215 (14)0.00005 (11)0.00133 (9)0.00063 (12)
C(21)0.00916 (12)0.01229 (17)0.01234 (13)0.00067 (11)0.00132 (9)0.00045 (11)
C(22)0.01621 (15)0.01549 (19)0.01670 (15)0.00369 (13)0.00259 (11)0.00338 (14)
C(30)0.01056 (12)0.01209 (17)0.01014 (13)0.00122 (11)0.00076 (9)0.00109 (11)
C(31)0.01196 (13)0.01239 (17)0.01003 (12)0.00035 (11)0.00027 (9)0.00084 (11)
C(32)0.01495 (14)0.01580 (19)0.01118 (14)0.00265 (13)0.00094 (10)0.00047 (12)
C(33)0.01401 (14)0.01450 (19)0.01360 (14)0.00260 (12)0.00082 (10)0.00106 (12)
C(34)0.01998 (19)0.0209 (2)0.0314 (2)0.00008 (16)0.01011 (16)0.00305 (19)
C(35)0.02192 (19)0.0181 (2)0.02149 (18)0.00728 (16)0.00207 (14)0.00186 (16)
C(40)0.01057 (12)0.01174 (17)0.01124 (13)0.00057 (11)0.00107 (9)0.00087 (12)
C(41)0.00987 (12)0.01296 (18)0.01380 (14)0.00044 (11)0.00083 (9)0.00196 (12)
C(42)0.01065 (13)0.0181 (2)0.01917 (16)0.00028 (12)0.00243 (11)0.00276 (15)
C(43)0.01365 (16)0.0215 (2)0.0322 (2)0.00400 (15)0.00321 (14)0.00586 (19)
C(44)0.01414 (16)0.0237 (2)0.0290 (2)0.00132 (15)0.00475 (14)0.00897 (19)
C(50)0.01079 (12)0.01419 (18)0.01177 (14)0.00209 (12)0.00066 (10)0.00043 (12)
C(51)0.01020 (12)0.01486 (18)0.01124 (13)0.00135 (11)0.00085 (9)0.00154 (12)
C(52)0.01321 (14)0.0200 (2)0.01166 (13)0.00270 (13)0.00180 (10)0.00253 (13)
C(53)0.01775 (16)0.0213 (2)0.01236 (14)0.00519 (14)0.00032 (11)0.00332 (14)
C(54)0.0279 (2)0.0288 (3)0.01571 (17)0.00378 (19)0.00086 (14)0.00822 (18)
C(55)0.01432 (17)0.0405 (3)0.01939 (17)0.00411 (18)0.00126 (12)0.0061 (2)
C(60)0.01141 (13)0.01535 (18)0.01248 (14)0.00131 (12)0.00054 (10)0.00049 (13)
C(61)0.01792 (17)0.01231 (19)0.01517 (16)0.00018 (13)0.00053 (13)0.00118 (14)
C(70)0.01331 (13)0.01267 (18)0.01246 (13)0.00162 (12)0.00024 (10)0.00027 (12)
C(71)0.01491 (14)0.01401 (18)0.01331 (14)0.00386 (12)0.00048 (10)0.00119 (13)
C(72)0.01985 (17)0.0207 (2)0.01490 (15)0.00717 (15)0.00424 (12)0.00278 (14)
C(73)0.0271 (2)0.0286 (3)0.01875 (18)0.0137 (2)0.00492 (15)0.00075 (18)
C(80)0.01117 (14)0.01001 (17)0.01459 (14)0.00029 (12)0.00107 (9)0.00106 (12)
C(81)0.00988 (12)0.01029 (16)0.01214 (13)0.00056 (11)0.00097 (9)0.00064 (11)
C(82)0.00940 (13)0.0127 (2)0.01484 (15)0.00032 (13)0.00030 (11)0.00006 (13)
C(83)0.01186 (13)0.01437 (18)0.01435 (14)0.00027 (12)0.00117 (10)0.00158 (12)
C(84)0.01640 (16)0.0234 (2)0.02060 (17)0.00350 (15)0.00561 (13)0.00300 (16)
C(85)0.01416 (14)0.0179 (2)0.01274 (14)0.00111 (13)0.00027 (11)0.00001 (13)
C(86)0.01464 (16)0.0252 (2)0.01227 (19)0.00472 (18)0.00011 (12)0.00133 (17)
C(87)0.02097 (19)0.0300 (3)0.0124 (2)0.0079 (2)0.00003 (14)0.00199 (19)
C(88)0.0256 (2)0.0434 (4)0.01309 (16)0.0116 (2)0.00181 (14)0.00152 (19)
C(90)0.00958 (13)0.01056 (17)0.01172 (14)0.00194 (12)0.00193 (10)0.00084 (12)
C(91)0.00983 (12)0.00923 (16)0.01246 (13)0.00066 (10)0.00110 (9)0.00026 (11)
C(92)0.01137 (13)0.01091 (17)0.01467 (14)0.00078 (11)0.00030 (10)0.00076 (12)
C(93)0.01975 (17)0.0164 (2)0.01452 (15)0.00304 (14)0.00274 (12)0.00148 (14)
C(94)0.01732 (15)0.01066 (18)0.01757 (15)0.00136 (13)0.00215 (11)0.00135 (13)
C(100)0.00834 (12)0.00973 (17)0.01335 (13)0.00016 (11)0.00027 (9)0.00065 (11)
C(101)0.00924 (12)0.00995 (16)0.01053 (12)0.00023 (10)0.00038 (9)0.00048 (11)
C(1E)0.00963 (12)0.01300 (17)0.01128 (12)0.00174 (11)0.00031 (9)0.00116 (11)
C(1F)0.01080 (12)0.01426 (18)0.01148 (13)0.00044 (11)0.00042 (9)0.00070 (12)
C(1G)0.01138 (14)0.0302 (3)0.01599 (15)0.00325 (14)0.00166 (11)0.00245 (16)
C(1H)0.01523 (14)0.01590 (19)0.01304 (14)0.00041 (13)0.00036 (10)0.00286 (13)
C(110)0.01991 (19)0.0150 (2)0.01045 (19)0.00488 (17)0.00466 (14)0.00253 (16)
C(111)0.01346 (15)0.01023 (19)0.01061 (15)0.00126 (11)0.00106 (12)0.00058 (12)
C(1I)0.01391 (14)0.01238 (18)0.01089 (13)0.00056 (12)0.00112 (10)0.00155 (12)
C(1J)0.01278 (13)0.01050 (17)0.01264 (13)0.00041 (11)0.00142 (10)0.00098 (11)
C(1K)0.01885 (16)0.01092 (19)0.01857 (16)0.00035 (13)0.00139 (12)0.00301 (13)
C(1L)0.01624 (15)0.01425 (19)0.01794 (16)0.00036 (13)0.00327 (12)0.00076 (14)
C(19)0.01522 (16)0.0252 (2)0.01882 (16)0.00240 (15)0.00583 (12)0.00877 (16)
C(49)0.0319 (2)0.0169 (2)0.01543 (16)0.00389 (17)0.01040 (15)0.00263 (15)
C(69)0.01236 (14)0.0176 (2)0.02140 (17)0.00262 (13)0.00191 (11)0.00298 (15)
C(79)0.01858 (18)0.0161 (2)0.01729 (16)0.00205 (15)0.00183 (13)0.00078 (14)
C(99)0.0211 (2)0.0351 (4)0.0201 (2)0.0174 (2)0.00942 (18)0.0103 (2)
C(98)0.00914 (12)0.01080 (17)0.02046 (16)0.00102 (11)0.00123 (10)0.00036 (13)
C(97)0.01665 (15)0.01337 (18)0.01157 (13)0.00087 (12)0.00167 (10)0.00213 (12)
Geometric parameters (Å, º) top
O(10)—C(10)1.2309 (5)C(61)—H(61A)1.0920
O(20)—C(20)1.2295 (5)C(61)—H(61B)1.0920
O(30)—C(30)1.2374 (5)C(70)—C(71)1.5352 (6)
O(40)—C(40)1.2391 (5)C(71)—C(72)1.5355 (6)
O(50)—C(50)1.2273 (6)C(71)—H(71)1.0990
O(60)—C(60)1.2314 (5)C(72)—C(73)1.5259 (7)
O(70)—C(70)1.2403 (5)C(72)—H(72A)1.0920
O(80)—C(80)1.2347 (6)C(72)—H(72B)1.0920
O(83)—H(83A)0.9670C(73)—H(73A)1.0590
O(83)—H(83B)0.9670C(73)—H(73B)1.0590
O(90)—C(90)1.2368 (5)C(73)—H(73C)1.0590
O(100)—C(100)1.2363 (5)C(80)—C(81)1.5355 (6)
O(112)—C(110)1.224 (3)C(81)—C(82)1.5384 (6)
O(82)—C(82)1.4179 (8)C(81)—H(81)1.0990
O(82)—H(82A)0.9650C(82)—H(82)1.0990
N(1)—C(10)1.3672 (6)C(83)—C(84)1.5279 (6)
N(1)—C(19)1.4654 (6)C(83)—H(83)1.0990
N(2)—C(11)1.4515 (6)C(84)—H(84A)1.0590
N(2)—C(20)1.3523 (6)C(84)—H(84B)1.0590
N(2)—H(2)1.0090C(84)—H(84C)1.0590
N(3)—C(21)1.4620 (5)C(85)—C(86)1.4955 (7)
N(3)—C(30)1.3443 (5)C(85)—H(85A)1.0920
N(3)—H(3)1.0090C(85)—H(85B)1.0920
N(4)—C(40)1.3541 (6)C(86)—C(87)1.3318 (8)
N(4)—C(49)1.4635 (6)C(86)—H(86)1.0770
N(5)—C(41)1.4527 (6)C(87)—C(88)1.4986 (8)
N(5)—C(50)1.3543 (5)C(87)—H(87)1.0770
N(5)—H(5)1.0090C(88)—H(88A)1.0590
N(6)—C(51)1.4670 (6)C(88)—H(88B)1.0590
N(6)—C(60)1.3560 (6)C(88)—H(88C)1.0590
N(6)—C(69)1.4643 (6)C(90)—C(91)1.5360 (6)
N(7)—C(61)1.4666 (7)C(91)—H(91)1.0990
N(7)—C(70)1.3526 (6)C(92)—C(93)1.5300 (6)
N(7)—C(79)1.4653 (7)C(92)—C(94)1.5344 (6)
N(8)—C(71)1.4611 (6)C(92)—H(92)1.0990
N(8)—C(80)1.3494 (5)C(93)—H(93A)1.0590
N(8)—H(8)1.0090C(93)—H(93B)1.0590
N(9)—C(90)1.3542 (7)C(93)—H(93C)1.0590
N(9)—C(99)1.4553 (17)C(94)—H(94A)1.0590
N(10)—C(100)1.3570 (5)C(94)—H(94B)1.0590
N(10)—C(98)1.4661 (5)C(94)—H(94C)1.0590
N(11)—C(110)1.346 (2)C(101)—C(1E)1.5336 (5)
N(11)—C(97)1.4640 (6)C(101)—H(101)1.0990
C(11)—C(12)1.5274 (7)C(1E)—C(1F)1.5396 (5)
C(11)—H(11)1.0990C(1E)—H(11E)1.0920
C(12)—H(12A)1.0590 (5)C(1E)—H(12E)1.0920
C(12)—H(12B)1.0590 (5)C(1F)—C(1G)1.5305 (6)
C(12)—H(12C)1.0590 (6)C(1F)—C(1H)1.5331 (6)
C(21)—C(22)1.5178 (6)C(1F)—H(1F)1.0990
C(21)—H(21)1.0990C(1G)—H(11G)1.0590
C(22)—H(22A)1.0590C(1G)—H(12G)1.0590
C(22)—H(22B)1.0590C(1G)—H(13G)1.0590
C(22)—H(22C)1.0590C(1H)—H(11H)1.0590
C(30)—C(31)1.5321 (5)C(1H)—H(12H)1.0590
C(31)—C(32)1.5265 (6)C(1H)—H(13H)1.0590
C(31)—H(31)1.0990C(110)—C(111)1.528 (2)
C(32)—H(32A)1.0920C(111)—C(1I)1.5281 (6)
C(32)—H(32B)1.0920C(111)—H(111)1.0000
C(33)—C(34)1.5300 (7)C(1I)—C(1J)1.5320 (6)
C(33)—C(35)1.5245 (7)C(1I)—H(11I)1.0920
C(33)—H(33)1.0990C(1I)—H(12I)1.0920
C(34)—H(34A)1.0590C(1J)—C(1K)1.5315 (6)
C(34)—H(34B)1.0590C(1J)—C(1L)1.5336 (6)
C(34)—H(34C)1.0590C(1J)—H(1J)1.0990
C(35)—H(35A)1.0590C(1K)—H(11K)1.0590
C(35)—H(35B)1.0590C(1K)—H(12K)1.0590
C(35)—H(35C)1.0590C(1K)—H(13K)1.0590
C(40)—C(41)1.5354 (6)C(1L)—H(11L)1.0590
C(41)—H(41)1.0990C(1L)—H(12L)1.0590
C(42)—C(43)1.5255 (7)C(1L)—H(13L)1.0590
C(42)—C(44)1.5333 (7)C(19)—H(19A)1.0660
C(42)—H(42)1.0990C(19)—H(19B)1.0660
C(43)—H(43A)1.0590C(19)—H(19C)1.0660
C(43)—H(43B)1.0590C(49)—H(49A)1.0660
C(43)—H(43C)1.0590C(49)—H(49B)1.0660
C(44)—H(44A)1.0590C(49)—H(49C)1.0660
C(44)—H(44B)1.0590C(69)—H(69A)1.0660
C(44)—H(44C)1.0590C(69)—H(69B)1.0660
C(50)—C(51)1.5379 (6)C(69)—H(69C)1.0660
C(51)—C(52)1.5290 (5)C(79)—H(79A)1.0660
C(51)—H(51)1.0990C(79)—H(79B)1.0660
C(52)—C(53)1.5336 (6)C(79)—H(79C)1.0660
C(52)—H(52A)1.0920C(79)—H(79D)1.0660
C(52)—H(52B)1.0920C(79)—H(79E)0.9776
C(53)—C(54)1.5285 (6)C(79)—H(79F)1.0660
C(53)—C(55)1.5315 (7)C(99)—H(99A)1.0660
C(53)—H(53)1.0990C(99)—H(99B)1.0660
C(54)—H(54A)1.0590C(99)—H(99C)1.0660
C(54)—H(54B)1.0590C(98)—H(98A)1.0660
C(54)—H(54C)1.0590C(98)—H(98B)1.0660
C(55)—H(55A)1.0590C(98)—H(98C)1.0660
C(55)—H(55B)1.0590C(97)—H(97A)1.0660
C(55)—H(55C)1.0590C(97)—H(97B)1.0660
C(60)—C(61)1.5314 (7)C(97)—H(97C)1.0660
C(10)—N(1)—C(19)122.91 (4)C(54)—C(53)—C(55)110.20 (4)
C(11)—N(2)—C(20)121.55 (4)O(60)—C(60)—N(6)122.86 (4)
C(21)—N(3)—C(30)121.48 (4)O(60)—C(60)—C(61)118.12 (4)
C(40)—N(4)—C(49)123.35 (4)N(6)—C(60)—C(61)119.00 (4)
C(41)—N(5)—C(50)121.05 (4)N(7)—C(61)—C(60)107.91 (4)
C(51)—N(6)—C(60)118.05 (4)O(70)—C(70)—N(7)120.46 (4)
C(51)—N(6)—C(69)117.40 (4)O(70)—C(70)—C(71)118.63 (4)
C(60)—N(6)—C(69)123.94 (4)N(7)—C(70)—C(71)120.89 (4)
C(61)—N(7)—C(70)114.49 (4)N(8)—C(71)—C(70)107.83 (3)
C(61)—N(7)—C(79)117.37 (4)N(8)—C(71)—C(72)108.84 (4)
C(70)—N(7)—C(79)125.69 (4)C(70)—C(71)—C(72)110.80 (3)
C(71)—N(8)—C(80)122.80 (4)C(71)—C(72)—C(73)113.56 (5)
C(90)—N(9)—C(99)123.89 (6)O(80)—C(80)—N(8)123.84 (4)
C(100)—N(10)—C(98)122.31 (4)O(80)—C(80)—C(81)121.22 (4)
C(110)—N(11)—C(97)118.45 (10)N(8)—C(80)—C(81)114.72 (4)
O(10)—C(10)—N(1)122.66 (4)C(80)—C(81)—C(82)112.28 (4)
N(2)—C(11)—C(12)108.97 (4)O(82)—C(82)—C(81)110.93 (4)
O(20)—C(20)—N(2)122.91 (4)C(85)—C(86)—C(87)124.40 (6)
N(3)—C(21)—C(22)109.97 (4)C(86)—C(87)—C(88)125.65 (6)
O(30)—C(30)—N(3)122.80 (4)O(90)—C(90)—N(9)122.74 (4)
O(30)—C(30)—C(31)121.06 (3)O(90)—C(90)—C(91)118.29 (4)
N(3)—C(30)—C(31)116.13 (4)N(9)—C(90)—C(91)118.97 (4)
C(30)—C(31)—C(32)109.28 (4)C(93)—C(92)—C(94)110.76 (3)
C(34)—C(33)—C(35)111.06 (4)O(100)—C(100)—N(10)122.38 (4)
O(40)—C(40)—N(4)121.81 (4)C(101)—C(1E)—C(1F)115.16 (3)
O(40)—C(40)—C(41)118.49 (4)C(1E)—C(1F)—C(1G)110.19 (3)
N(4)—C(40)—C(41)119.63 (3)C(1E)—C(1F)—C(1H)111.06 (3)
N(5)—C(41)—C(40)109.77 (3)C(1G)—C(1F)—C(1H)110.77 (4)
C(43)—C(42)—C(44)110.59 (4)O(112)—C(110)—N(11)120.61 (16)
O(50)—C(50)—N(5)123.27 (4)O(112)—C(110)—C(111)119.07 (16)
O(50)—C(50)—C(51)120.97 (4)N(11)—C(110)—C(111)120.30 (16)
N(5)—C(50)—C(51)115.63 (4)C(110)—C(111)—C(1I)109.70 (8)
N(6)—C(51)—C(50)111.23 (3)C(110)—C(111)—H(111)108.05 (9)
N(6)—C(51)—C(52)112.59 (4)C(111)—C(1I)—C(1J)114.22 (3)
C(50)—C(51)—C(52)113.24 (3)C(1I)—C(1J)—C(1K)109.12 (3)
C(51)—C(52)—C(53)112.04 (3)C(1I)—C(1J)—C(1L)110.75 (3)
C(52)—C(53)—C(54)110.81 (4)C(1I)—C(1J)—H(1J)108.56 (3)
C(52)—C(53)—C(55)111.67 (4)C(1K)—C(1J)—C(1L)110.99 (4)
 

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