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Crystals of the title compound, C16H28N2O7, were successfully grown from an oily product at low temperature (below 260 K). There are two independent mol­ecules in the asymmetric unit. One mol­ecule has a cis and the other a trans conformation at the urethane linkage, —O—CO—NH—. Independent mol­ecules are linked into dimers, but not into chains, by N—H...O=C hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014831/lh6080sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014831/lh6080Isup2.hkl
Contains datablock I

CCDC reference: 221683

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.089
  • wR factor = 0.193
  • Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
ATOM_007 Alert A _atom_site_aniso_label is missing Unique label identifying the atom site.
Yellow Alert Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54184 PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C133 - C134 = 1.37 Ang. PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C134 - C135 = 1.43 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 68.25 From the CIF: _reflns_number_total 3190 Count of symmetry unique reflns 3258 Completeness (_total/calc) 97.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC and Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.

tert-butoxycarbonyl-L-alanyl-L-proline methyl ester top
Crystal data top
C14H24N2O5F(000) = 648.00
Mr = 300.35? # Insert any comments here.
Monoclinic, P21Dx = 1.190 Mg m3
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 10.131 (5) ÅCell parameters from 4739 reflections
b = 9.940 (5) Åθ = 6.3–62.2°
c = 16.784 (8) ŵ = 0.75 mm1
β = 97.33 (3)°T = 173 K
V = 1676.4 (14) Å3Platelet, colorless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Rigaku RAXIS-RAPID
diffractometer
2122 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.040
ω scansθmax = 68.3°
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
h = 1211
Tmin = 0.841, Tmax = 0.928k = 1111
31310 measured reflectionsl = 1919
3190 independent reflections
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.089 w = 1/[0.001Fo2 + 3σ(Fo2) + 0.5]/(4Fo2)
wR(F2) = 0.193(Δ/σ)max = 0.007
S = 1.76Δρmax = 0.59 e Å3
2134 reflectionsΔρmin = 0.33 e Å3
217 parameters
Special details top

Experimental. ? #Insert any special details here.

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(111)0.0826 (6)0.3912 (6)0.3556 (4)0.0543 (17)*
O(112)0.1819 (7)0.1928 (7)0.3247 (4)0.0682 (19)*
O(121)0.0686 (6)0.5082 (7)0.1774 (4)0.0631 (19)*
O(131)0.0892 (6)0.8114 (7)0.0994 (4)0.0619 (18)*
O(141)0.1319 (6)0.8192 (7)0.0673 (4)0.0553 (17)*
O(211)0.4687 (5)0.0359 (7)0.3815 (3)0.0537 (16)*
O(212)0.6203 (7)0.0349 (7)0.2908 (4)0.0679 (19)*
O(221)0.4898 (6)0.3141 (7)0.2287 (4)0.0649 (19)*
O(231)0.4858 (6)0.4659 (6)0.0570 (4)0.0599 (16)*
O(241)0.6296 (6)0.5991 (7)0.1347 (3)0.0502 (16)*
N(121)0.2623 (8)0.3972 (8)0.2933 (5)0.057 (2)*
N(131)0.0617 (7)0.6983 (8)0.2484 (4)0.049 (2)*
N(221)0.4122 (8)0.0475 (8)0.2588 (4)0.054 (2)*
N(231)0.6141 (6)0.2397 (7)0.1385 (4)0.0382 (16)*
C(111)0.0376 (10)0.3283 (11)0.3802 (6)0.062 (3)*
C(112)0.0021 (11)0.2469 (13)0.4552 (6)0.090 (4)*
C(113)0.1102 (10)0.2474 (12)0.3155 (6)0.073 (3)*
C(114)0.1223 (10)0.4522 (14)0.3946 (8)0.106 (4)*
C(115)0.1766 (9)0.3176 (11)0.3252 (6)0.054 (3)*
C(121)0.2450 (8)0.5432 (9)0.2858 (5)0.048 (2)*
C(122)0.1167 (8)0.5783 (10)0.2340 (5)0.043 (2)*
C(123)0.3615 (8)0.6009 (10)0.2476 (5)0.058 (3)*
C(131)0.0510 (9)0.7498 (11)0.1981 (6)0.062 (3)*
C(132)0.0231 (9)0.7947 (9)0.1171 (5)0.049 (2)*
C(133)0.0851 (14)0.8766 (16)0.2457 (8)0.118 (5)*
C(134)0.0059 (15)0.8791 (18)0.3180 (10)0.141 (6)*
C(135)0.1017 (11)0.7855 (11)0.3172 (7)0.074 (3)*
C(141)0.1183 (9)0.8733 (10)0.0114 (5)0.058 (3)*
C(211)0.5611 (9)0.0946 (10)0.4472 (5)0.052 (3)*
C(212)0.6760 (9)0.0007 (10)0.4702 (6)0.066 (3)*
C(213)0.6065 (9)0.2327 (10)0.4239 (6)0.068 (3)*
C(214)0.4750 (10)0.1080 (12)0.5116 (6)0.074 (3)*
C(215)0.5087 (9)0.0101 (10)0.3089 (5)0.049 (2)*
C(221)0.4379 (9)0.0903 (11)0.1798 (5)0.054 (2)*
C(222)0.5182 (8)0.2206 (9)0.1839 (5)0.045 (2)*
C(223)0.3069 (9)0.1146 (11)0.1260 (6)0.067 (3)*
C(231)0.6787 (8)0.3714 (8)0.1354 (5)0.039 (2)*
C(232)0.5838 (9)0.4799 (10)0.1048 (5)0.048 (2)*
C(233)0.7847 (10)0.3498 (10)0.0796 (6)0.062 (3)*
C(234)0.8126 (10)0.1978 (11)0.0849 (6)0.066 (3)*
C(235)0.6784 (8)0.1357 (9)0.0951 (5)0.046 (2)*
C(241)0.5571 (9)0.7189 (10)0.1029 (6)0.062 (3)*
H(1)0.08030.20690.47040.108*
H(2)0.05940.17860.44550.108*
H(3)0.03690.30390.49710.108*
H(4)0.19320.22000.33090.087*
H(5)0.12530.29970.26780.087*
H(6)0.05920.17010.30600.087*
H(7)0.07540.50680.43530.127*
H(8)0.13970.50250.34630.126*
H(9)0.20390.42370.41130.127*
H(10)0.33790.35740.27460.068*
H(11)0.24450.58140.33770.058*
H(12)0.44260.57920.27990.070*
H(13)0.36170.56340.19550.070*
H(14)0.35270.69580.24340.070*
H(15)0.12230.68700.19370.074*
H(16)0.07000.95520.21590.142*
H(17)0.17590.87340.25440.142*
H(18)0.02920.96710.32750.169*
H(19)0.05710.85530.35950.169*
H(20)0.11350.73450.36550.089*
H(21)0.18200.83130.31100.089*
H(22)0.07320.95720.00570.070*
H(23)0.06880.81210.03940.070*
H(24)0.20400.88570.04070.070*
H(25)0.73530.03970.51230.079*
H(26)0.72160.01450.42500.079*
H(27)0.64360.08240.48790.079*
H(28)0.53110.28660.40540.081*
H(29)0.66150.22410.38240.081*
H(30)0.65550.27460.46930.081*
H(31)0.44310.02180.52440.089*
H(32)0.40180.16490.49390.089*
H(33)0.52490.14580.55800.089*
H(34)0.32660.06050.27500.065*
H(35)0.48630.02180.15670.064*
H(36)0.25770.1830.14890.081*
H(37)0.32490.14250.07430.081*
H(38)0.25660.03370.12110.081*
H(39)0.72050.39460.18750.047*
H(40)0.75220.37520.02620.074*
H(41)0.86280.39960.09750.074*
H(42)0.84340.16610.03720.079*
H(43)0.87660.17750.12970.079*
H(44)0.68930.05490.12550.056*
H(45)0.62840.11760.04440.056*
H(46)0.59750.79690.12810.074*
H(47)0.55940.72410.04660.074*
H(48)0.46730.71330.11340.074*
Geometric parameters (Å, º) top
O(111)—C(111)1.474 (12)C(131)—C(133)1.555 (18)
O(111)—C(115)1.351 (12)C(131)—H(15)0.95
O(112)—C(115)1.242 (13)C(133)—C(134)1.37 (2)
O(121)—C(122)1.228 (11)C(133)—H(16)0.95
O(131)—C(132)1.223 (11)C(133)—H(17)0.95
O(141)—C(132)1.318 (11)C(134)—C(135)1.43 (2)
O(141)—C(141)1.449 (11)C(134)—H(18)0.95
O(211)—C(211)1.473 (10)C(134)—H(19)0.95
O(211)—C(215)1.357 (10)C(135)—H(20)0.95
O(212)—C(215)1.232 (12)C(135)—H(21)0.95
O(221)—C(222)1.252 (11)C(141)—H(22)0.95
O(231)—C(232)1.202 (11)C(141)—H(23)0.95
O(241)—C(232)1.346 (12)C(141)—H(24)0.95
O(241)—C(241)1.464 (12)C(211)—C(212)1.504 (13)
N(121)—C(115)1.336 (13)C(211)—C(213)1.515 (14)
N(121)—C(121)1.465 (12)C(211)—C(214)1.479 (13)
N(121)—H(10)0.95C(212)—H(25)0.95
N(131)—C(122)1.351 (12)C(212)—H(26)0.95
N(131)—C(131)1.426 (12)C(212)—H(27)0.95
N(131)—C(135)1.459 (13)C(213)—H(28)0.95
N(221)—C(215)1.335 (12)C(213)—H(29)0.95
N(221)—C(221)1.447 (11)C(213)—H(30)0.95
N(221)—H(34)0.95C(214)—H(31)0.95
N(231)—C(222)1.323 (10)C(214)—H(32)0.95
N(231)—C(231)1.467 (11)C(214)—H(33)0.95
N(231)—C(235)1.464 (11)C(221)—C(222)1.526 (14)
C(111)—C(112)1.501 (15)C(221)—C(223)1.526 (13)
C(111)—C(113)1.471 (15)C(221)—H(35)0.95
C(111)—C(114)1.538 (17)C(223)—H(36)0.95
C(112)—H(1)0.95C(223)—H(37)0.95
C(112)—H(2)0.95C(223)—H(38)0.95
C(112)—H(3)0.95C(231)—C(232)1.492 (12)
C(113)—H(4)0.95C(231)—C(233)1.527 (13)
C(113)—H(5)0.95C(231)—H(39)0.95
C(113)—H(6)0.95C(233)—C(234)1.538 (15)
C(114)—H(7)0.95C(233)—H(40)0.95
C(114)—H(8)0.95C(233)—H(41)0.95
C(114)—H(9)0.95C(234)—C(235)1.523 (13)
C(121)—C(122)1.510 (12)C(234)—H(42)0.95
C(121)—C(123)1.525 (12)C(234)—H(43)0.95
C(121)—H(11)0.95C(235)—H(44)0.95
C(123)—H(12)0.95C(235)—H(45)0.95
C(123)—H(13)0.95C(241)—H(46)0.95
C(123)—H(14)0.95C(241)—H(47)0.95
C(131)—C(132)1.492 (13)C(241)—H(48)0.95
C(111)—O(111)—C(115)121.6 (8)H(21)—C(135)—C(134)110.7
C(132)—O(141)—C(141)118.5 (7)N(131)—C(135)—C(134)105.0 (10)
C(211)—O(211)—C(215)120.9 (7)H(22)—C(141)—H(23)109.5
C(232)—O(241)—C(241)116.6 (6)H(22)—C(141)—H(24)109.5
C(115)—N(121)—C(121)122.9 (8)H(22)—C(141)—O(141)109.6
C(115)—N(121)—H(10)118.6H(23)—C(141)—H(24)109.5
C(121)—N(121)—H(10)118.5H(23)—C(141)—O(141)109.3
C(122)—N(131)—C(131)121.9 (7)H(24)—C(141)—O(141)109.5
C(122)—N(131)—C(135)126.0 (7)C(212)—C(211)—C(213)112.2 (8)
C(131)—N(131)—C(135)112.1 (8)C(212)—C(211)—C(214)112.2 (8)
C(215)—N(221)—C(221)120.1 (8)C(212)—C(211)—O(211)110.1 (8)
C(215)—N(221)—H(34)120.0C(213)—C(211)—C(214)109.5 (9)
C(221)—N(221)—H(34)119.9C(213)—C(211)—O(211)110.5 (7)
C(222)—N(231)—C(231)120.9 (7)C(214)—C(211)—O(211)101.8 (7)
C(222)—N(231)—C(235)126.2 (7)H(25)—C(212)—H(26)109.5
C(231)—N(231)—C(235)112.5 (6)H(25)—C(212)—H(27)109.5
C(112)—C(111)—C(113)111.6 (9)H(25)—C(212)—C(211)109.5
C(112)—C(111)—C(114)112.2 (9)H(26)—C(212)—H(27)109.5
C(112)—C(111)—O(111)110.2 (8)H(26)—C(212)—C(211)109.5
C(113)—C(111)—C(114)108.5 (9)H(27)—C(212)—C(211)109.5
C(113)—C(111)—O(111)112.3 (8)H(28)—C(213)—H(29)109.5
C(114)—C(111)—O(111)101.7 (9)H(28)—C(213)—H(30)109.5
H(1)—C(112)—H(2)109.5H(28)—C(213)—C(211)109.5
H(1)—C(112)—H(3)109.5H(29)—C(213)—H(30)109.5
H(1)—C(112)—C(111)109.5H(29)—C(213)—C(211)109.5
H(2)—C(112)—H(3)109.5H(30)—C(213)—C(211)109.5
H(2)—C(112)—C(111)109.5H(31)—C(214)—H(32)109.5
H(3)—C(112)—C(111)109.5H(31)—C(214)—H(33)109.5
H(4)—C(113)—H(5)109.5H(31)—C(214)—C(211)109.5
H(4)—C(113)—H(6)109.5H(32)—C(214)—H(33)109.5
H(4)—C(113)—C(111)109.4H(32)—C(214)—C(211)109.5
H(5)—C(113)—H(6)109.5H(33)—C(214)—C(211)109.5
H(5)—C(113)—C(111)109.5O(211)—C(215)—O(212)124.9 (8)
H(6)—C(113)—C(111)109.5O(211)—C(215)—N(221)111.7 (8)
H(7)—C(114)—H(8)109.5O(212)—C(215)—N(221)123.4 (8)
H(7)—C(114)—H(9)109.5C(222)—C(221)—C(223)108.1 (8)
H(7)—C(114)—C(111)109.5C(222)—C(221)—H(35)109.1
H(8)—C(114)—H(9)109.5C(222)—C(221)—N(221)111.4 (7)
H(8)—C(114)—C(111)109.5C(223)—C(221)—H(35)109.1
H(9)—C(114)—C(111)109.4C(223)—C(221)—N(221)110.2 (7)
O(111)—C(115)—O(112)125.1 (9)H(35)—C(221)—N(221)109.0
O(111)—C(115)—N(121)110.9 (9)O(221)—C(222)—N(231)118.8 (8)
O(112)—C(115)—N(121)123.9 (9)O(221)—C(222)—C(221)119.7 (8)
C(122)—C(121)—C(123)109.0 (7)N(231)—C(222)—C(221)121.5 (8)
C(122)—C(121)—H(11)109.3H(36)—C(223)—H(37)109.5
C(122)—C(121)—N(121)111.3 (7)H(36)—C(223)—H(38)109.5
C(123)—C(121)—H(11)109.3H(36)—C(223)—C(221)109.5
C(123)—C(121)—N(121)108.5 (7)H(37)—C(223)—H(38)109.5
H(11)—C(121)—N(121)109.3H(37)—C(223)—C(221)109.5
O(121)—C(122)—N(131)120.5 (7)H(38)—C(223)—C(221)109.4
O(121)—C(122)—C(121)122.9 (8)C(232)—C(231)—C(233)111.3 (7)
N(131)—C(122)—C(121)116.4 (7)C(232)—C(231)—H(39)109.4
H(12)—C(123)—H(13)109.5C(232)—C(231)—N(231)112.7 (7)
H(12)—C(123)—H(14)109.5C(233)—C(231)—H(39)109.4
H(12)—C(123)—C(121)109.5C(233)—C(231)—N(231)104.4 (7)
H(13)—C(123)—H(14)109.5H(39)—C(231)—N(231)109.4
H(13)—C(123)—C(121)109.4O(231)—C(232)—O(241)124.5 (9)
H(14)—C(123)—C(121)109.5O(231)—C(232)—C(231)125.9 (9)
C(132)—C(131)—C(133)107.8 (9)O(241)—C(232)—C(231)109.4 (7)
C(132)—C(131)—H(15)110.8C(234)—C(233)—H(40)110.9
C(132)—C(131)—N(131)114.6 (8)C(234)—C(233)—H(41)110.8
C(133)—C(131)—H(15)110.9C(234)—C(233)—C(231)104.0 (8)
C(133)—C(131)—N(131)101.6 (8)H(40)—C(233)—H(41)109.5
H(15)—C(131)—N(131)110.7H(40)—C(233)—C(231)110.8
O(131)—C(132)—O(141)123.3 (8)H(41)—C(233)—C(231)110.8
O(131)—C(132)—C(131)123.5 (8)C(235)—C(234)—H(42)110.7
O(141)—C(132)—C(131)113.1 (8)C(235)—C(234)—H(43)110.8
C(134)—C(133)—H(16)109.7C(235)—C(234)—C(233)104.2 (8)
C(134)—C(133)—H(17)109.5H(42)—C(234)—H(43)109.5
C(134)—C(133)—C(131)109.1 (13)H(42)—C(234)—C(233)110.8
H(16)—C(133)—H(17)109.5H(43)—C(234)—C(233)110.8
H(16)—C(133)—C(131)109.6H(44)—C(235)—H(45)109.5
H(17)—C(133)—C(131)109.5H(44)—C(235)—N(231)110.9
C(135)—C(134)—H(18)109.3H(44)—C(235)—C(234)111.0
C(135)—C(134)—H(19)109.4H(45)—C(235)—N(231)111.0
C(135)—C(134)—C(133)109.9 (14)H(45)—C(235)—C(234)111.0
H(18)—C(134)—H(19)109.5N(231)—C(235)—C(234)103.3 (7)
H(18)—C(134)—C(133)109.3H(46)—C(241)—H(47)109.5
H(19)—C(134)—C(133)109.5H(46)—C(241)—H(48)109.5
H(20)—C(135)—H(21)109.5H(46)—C(241)—O(241)109.5
H(20)—C(135)—N(131)110.5H(47)—C(241)—H(48)109.5
H(20)—C(135)—C(134)110.5H(47)—C(241)—O(241)109.4
H(21)—C(135)—N(131)110.7H(48)—C(241)—O(241)109.4
C(115)—O(111)—C(111)—C(112)71.0 (11)H(11)—C(121)—C(123)—H(12)60.6
C(115)—O(111)—C(111)—C(113)54.1 (12)H(11)—C(121)—C(123)—H(13)179.5
C(115)—O(111)—C(111)—C(114)169.8 (7)H(11)—C(121)—C(123)—H(14)59.6
C(111)—O(111)—C(115)—O(112)10.1 (14)N(131)—C(131)—C(132)—O(131)13.6 (14)
C111—O111—C115—N121168.1 (6)N131—C131—C132—O141168.7 (8)
C(141)—O(141)—C(132)—O(131)2.3 (13)C(133)—C(131)—C(132)—O(131)98.7 (11)
C141—O141—C132—C131175.4 (7)C(133)—C(131)—C(132)—O(141)79.0 (9)
C(132)—O(141)—C(141)—H(22)60.0H(15)—C(131)—C(132)—O(131)139.8
C(132)—O(141)—C(141)—H(23)60.0H(15)—C(131)—C(132)—O(141)42.5
C(132)—O(141)—C(141)—H(24)179.9N(131)—C(131)—C(133)—C(134)6.5 (14)
C(215)—O(211)—C(211)—C(212)62.4 (10)N(131)—C(131)—C(133)—H(16)113.6
C(215)—O(211)—C(211)—C(213)62.1 (10)N(131)—C(131)—C(133)—H(17)126.4
C(215)—O(211)—C(211)—C(214)178.4 (7)C(132)—C(131)—C(133)—C(134)127.3 (12)
C(211)—O(211)—C(215)—O(212)1.7 (14)C(132)—C(131)—C(133)—H(16)7.3
C211—O211—C215—N221177.6 (7)C(132)—C(131)—C(133)—H(17)112.8
C(241)—O(241)—C(232)—O(231)3.1 (12)H(15)—C(131)—C(133)—C(134)111.2
C241—O241—C232—C231172.6 (6)H(15)—C(131)—C(133)—H(16)128.8
C(232)—O(241)—C(241)—H(46)179.8H(15)—C(131)—C(133)—H(17)8.8
C(232)—O(241)—C(241)—H(47)60.0C(131)—C(133)—C(134)—C(135)14.3 (17)
C(232)—O(241)—C(241)—H(48)59.8C(131)—C(133)—C(134)—H(18)134.2
C121—N121—C115—O1116.0 (13)C(131)—C(133)—C(134)—H(19)105.9
C(121)—N(121)—C(115)—O(112)172.4 (8)H(16)—C(133)—C(134)—C(135)105.7
H(10)—N(121)—C(115)—O(111)174.1H(16)—C(133)—C(134)—H(18)14.2
H(10)—N(121)—C(115)—O(112)7.6H(16)—C(133)—C(134)—H(19)134.2
C115—N121—C121—C12260.4 (11)H(17)—C(133)—C(134)—C(135)134.1
C(115)—N(121)—C(121)—C(123)179.6 (7)H(17)—C(133)—C(134)—H(18)105.9
C(115)—N(121)—C(121)—H(11)60.4H(17)—C(133)—C(134)—H(19)14.0
H(10)—N(121)—C(121)—C(122)119.6C(133)—C(134)—C(135)—N(131)15.9 (16)
H(10)—N(121)—C(121)—C(123)0.5C(133)—C(134)—C(135)—H(20)135.1
H(10)—N(121)—C(121)—H(11)119.6C(133)—C(134)—C(135)—H(21)103.5
C(131)—N(131)—C(122)—O(121)1.6 (13)H(18)—C(134)—C(135)—N(131)135.9
C131—N131—C122—C121173.0 (7)H(18)—C(134)—C(135)—H(20)105.0
C(135)—N(131)—C(122)—O(121)174.3 (8)H(18)—C(134)—C(135)—H(21)16.4
C(135)—N(131)—C(122)—C(121)11.1 (13)H(19)—C(134)—C(135)—N(131)105.0
C122—N131—C131—C13271.1 (11)H(19)—C(134)—C(135)—H(20)14.9
C(122)—N(131)—C(131)—C(133)173.0 (9)H(19)—C(134)—C(135)—H(21)135.9
C(122)—N(131)—C(131)—H(15)55.2O(211)—C(211)—C(212)—H(25)179.6
C(135)—N(131)—C(131)—C(132)112.4 (9)O(211)—C(211)—C(212)—H(26)59.6
C(135)—N(131)—C(131)—C(133)3.5 (11)O(211)—C(211)—C(212)—H(27)60.5
C(135)—N(131)—C(131)—H(15)121.3C(213)—C(211)—C(212)—H(25)56.0
C(122)—N(131)—C(135)—C(134)164.5 (10)C(213)—C(211)—C(212)—H(26)64.0
C(122)—N(131)—C(135)—H(20)45.3C(213)—C(211)—C(212)—H(27)176.0
C(122)—N(131)—C(135)—H(21)76.1C(214)—C(211)—C(212)—H(25)67.8
C(131)—N(131)—C(135)—C(134)11.8 (12)C(214)—C(211)—C(212)—H(26)172.2
C(131)—N(131)—C(135)—H(20)131.0C(214)—C(211)—C(212)—H(27)52.2
C(131)—N(131)—C(135)—H(21)107.6O(211)—C(211)—C(213)—H(28)51.7
C221—N221—C215—O211176.3 (7)O(211)—C(211)—C(213)—H(29)68.4
C(221)—N(221)—C(215)—O(212)3.0 (14)O(211)—C(211)—C(213)—H(30)171.7
H(34)—N(221)—C(215)—O(211)3.6C(212)—C(211)—C(213)—H(28)175.1
H(34)—N(221)—C(215)—O(212)177.0C(212)—C(211)—C(213)—H(29)55.0
C215—N221—C221—C22276.3 (11)C(212)—C(211)—C(213)—H(30)65.0
C(215)—N(221)—C(221)—C(223)163.8 (8)C(214)—C(211)—C(213)—H(28)59.7
C(215)—N(221)—C(221)—H(35)44.1C(214)—C(211)—C(213)—H(29)179.8
H(34)—N(221)—C(221)—C(222)103.6C(214)—C(211)—C(213)—H(30)60.3
H(34)—N(221)—C(221)—C(223)16.3O(211)—C(211)—C(214)—H(31)60.2
H(34)—N(221)—C(221)—H(35)136.0O(211)—C(211)—C(214)—H(32)59.8
C(231)—N(231)—C(222)—O(221)5.0 (12)O(211)—C(211)—C(214)—H(33)179.9
C231—N231—C222—C221172.0 (7)C(212)—C(211)—C(214)—H(31)57.5
C(235)—N(231)—C(222)—O(221)167.2 (7)C(212)—C(211)—C(214)—H(32)177.5
C(235)—N(231)—C(222)—C(221)15.8 (12)C(212)—C(211)—C(214)—H(33)62.4
C222—N231—C231—C23261.0 (9)C(213)—C(211)—C(214)—H(31)177.2
C(222)—N(231)—C(231)—C(233)178.1 (6)C(213)—C(211)—C(214)—H(32)57.2
C(222)—N(231)—C(231)—H(39)61.1C(213)—C(211)—C(214)—H(33)62.88
C(235)—N(231)—C(231)—C(232)125.8 (7)N(221)—C(221)—C(222)—O(221)42.7 (11)
C(235)—N(231)—C(231)—C(233)4.9 (8)N221—C221—C222—N231140.3 (8)
C(235)—N(231)—C(231)—H(39)112.1C(223)—C(221)—C(222)—O(221)78.5 (10)
C(222)—N(231)—C(235)—C(234)156.4 (7)C(223)—C(221)—C(222)—N(231)98.6 (9)
C(222)—N(231)—C(235)—H(44)37.3H(35)—C(221)—C(222)—O(221)163.1
C(222)—N(231)—C(235)—H(45)84.6H(35)—C(221)—C(222)—N(231)19.9
C(231)—N(231)—C(235)—C(234)16.4 (8)N(221)—C(221)—C(223)—H(36)60.2
C(231)—N(231)—C(235)—H(44)135.4N(221)—C(221)—C(223)—H(37)179.9
C(231)—N(231)—C(235)—H(45)102.7N(221)—C(221)—C(223)—H(38)60.1
O(111)—C(111)—C(112)—H(1)180.0C(222)—C(221)—C(223)—H(36)61.7
O(111)—C(111)—C(112)—H(2)59.9C(222)—C(221)—C(223)—H(37)58.2
O(111)—C(111)—C(112)—H(3)60.1C(222)—C(221)—C(223)—H(38)178.0
C(113)—C(111)—C(112)—H(1)54.6H(35)—C(221)—C(223)—H(36)179.8
C(113)—C(111)—C(112)—H(2)65.5H(35)—C(221)—C(223)—H(37)60.3
C(113)—C(111)—C(112)—H(3)174.5H(35)—C(221)—C(223)—H(38)59.5
C(114)—C(111)—C(112)—H(1)67.5N(231)—C(231)—C(232)—O(231)30.9 (12)
C(114)—C(111)—C(112)—H(2)172.4N231—C231—C232—O241153.3 (7)
C(114)—C(111)—C(112)—H(3)52.4C(233)—C(231)—C(232)—O(231)85.9 (11)
O(111)—C(111)—C(113)—H(4)171.3C(233)—C(231)—C(232)—O(241)89.8 (8)
O(111)—C(111)—C(113)—H(5)51.4H(39)—C(231)—C(232)—O(231)153.0
O(111)—C(111)—C(113)—H(6)68.7H(39)—C(231)—C(232)—O(241)31.4
C(112)—C(111)—C(113)—H(4)64.4N(231)—C(231)—C(233)—C(234)24.0 (8)
C(112)—C(111)—C(113)—H(5)175.7N(231)—C(231)—C(233)—H(40)95.1
C(112)—C(111)—C(113)—H(6)55.6N(231)—C(231)—C(233)—H(41)143.0
C(114)—C(111)—C(113)—H(4)59.8C(232)—C(231)—C(233)—C(234)145.9 (7)
C(114)—C(111)—C(113)—H(5)59.8C(232)—C(231)—C(233)—H(40)26.8
C(114)—C(111)—C(113)—H(6)179.8C(232)—C(231)—C(233)—H(41)95.1
O(111)—C(111)—C(114)—H(7)59.9H(39)—C(231)—C(233)—C(234)93.0
O(111)—C(111)—C(114)—H(8)60.1H(39)—C(231)—C(233)—H(40)147.9
O(111)—C(111)—C(114)—H(9)179.8H(39)—C(231)—C(233)—H(41)26.0
C(112)—C(111)—C(114)—H(7)57.8C(231)—C(233)—C(234)—C(235)34.2 (9)
C(112)—C(111)—C(114)—H(8)177.9C(231)—C(233)—C(234)—H(42)153.3
C(112)—C(111)—C(114)—H(9)62.0C(231)—C(233)—C(234)—H(43)85.0
C(113)—C(111)—C(114)—H(7)178.4H(40)—C(233)—C(234)—C(235)84.9
C(113)—C(111)—C(114)—H(8)58.3H(40)—C(233)—C(234)—H(42)34.2
C(113)—C(111)—C(114)—H(9)61.8H(40)—C(233)—C(234)—H(43)155.9
N(121)—C(121)—C(122)—O(121)32.4 (11)H(41)—C(233)—C(234)—C(235)153.2
N121—C121—C122—N131153.2 (8)H(41)—C(233)—C(234)—H(42)87.6
C(123)—C(121)—C(122)—O(121)87.3 (10)H(41)—C(233)—C(234)—H(43)34.1
C(123)—C(121)—C(122)—N(131)87.2 (9)C(233)—C(234)—C(235)—N(231)30.8 (9)
H(11)—C(121)—C(122)—O(121)153.3C(233)—C(234)—C(235)—H(44)149.7
H(11)—C(121)—C(122)—N(131)32.3C(233)—C(234)—C(235)—H(45)88.3
N(121)—C(121)—C(123)—H(12)58.6H(42)—C(234)—C(235)—N(231)149.9
N(121)—C(121)—C(123)—H(13)61.3H(42)—C(234)—C(235)—H(44)91.1
N(121)—C(121)—C(123)—H(14)178.7H(42)—C(234)—C(235)—H(45)30.5
C(122)—C(121)—C(123)—H(12)180.0H(43)—C(234)—C(235)—N(231)88.5
C(122)—C(121)—C(123)—H(13)60.1H(43)—C(234)—C(235)—H(44)30.5
C(122)—C(121)—C(123)—H(14)59.8H(43)—C(234)—C(235)—H(45)152.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N121—H10···O2210.951.862.794 (12)168
N221—H34···O1120.952.213.070 (11)150
 

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