cis- and trans-Conformers at the urethane linkage: tert-butoxy­carbonyl-l-alanyl-l-proline methyl ester (Boc-l-Ala-l-Pro-OMe)

Oku, H.; Yamada, K.; Katakai, R.

doi:10.1107/S1600536803014831

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cis- and trans-Conformers at the urethane linkage: tert-butoxycarbonyl-L-alanyl-L-proline methyl ester (Boc-L-Ala-L-Pro-OMe)

H. Oku, K. Yamada and R. Katakai

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014831/lh6080sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014831/lh6080Isup2.hkl Contains datablock I

CCDC reference: 221683

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (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


 Alert Level A:



ATOM_007  Alert A _atom_site_aniso_label is missing
          Unique label identifying the atom site.


 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

C₁₄H₂₄N₂O₅	F(000) = 648.00
M_r = 300.35	? # Insert any comments here.
Monoclinic, P2₁	D_x = 1.190 Mg m⁻³
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54184 Å
a = 10.131 (5) Å	Cell parameters from 4739 reflections
b = 9.940 (5) Å	θ = 6.3–62.2°
c = 16.784 (8) Å	µ = 0.75 mm⁻¹
β = 97.33 (3)°	T = 173 K
V = 1676.4 (14) Å³	Platelet, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Rigaku RAXIS-RAPID diffractometer	2122 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.040
ω scans	θ_max = 68.3°
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	h = −12→11
T_min = 0.841, T_max = 0.928	k = −11→11
31310 measured reflections	l = −19→19
3190 independent reflections

Refinement top

Refinement on F²	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.089	w = 1/[0.001F_o² + 3σ(F_o²) + 0.5]/(4F_o²)
wR(F²) = 0.193	(Δ/σ)_max = 0.007
S = 1.76	Δρ_max = 0.59 e Å⁻³
2134 reflections	Δρ_min = −0.33 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)	−0.0803	0.2069	0.4704	0.108*
H(2)	0.0594	0.1786	0.4455	0.108*
H(3)	0.0369	0.3039	0.4971	0.108*
H(4)	−0.1932	0.2200	0.3309	0.087*
H(5)	−0.1253	0.2997	0.2678	0.087*
H(6)	−0.0592	0.1701	0.3060	0.087*
H(7)	−0.0754	0.5068	0.4353	0.127*
H(8)	−0.1397	0.5025	0.3463	0.126*
H(9)	−0.2039	0.4237	0.4113	0.127*
H(10)	0.3379	0.3574	0.2746	0.068*
H(11)	0.2445	0.5814	0.3377	0.058*
H(12)	0.4426	0.5792	0.2799	0.070*
H(13)	0.3617	0.5634	0.1955	0.070*
H(14)	0.3527	0.6958	0.2434	0.070*
H(15)	−0.1223	0.6870	0.1937	0.074*
H(16)	−0.0700	0.9552	0.2159	0.142*
H(17)	−0.1759	0.8734	0.2544	0.142*
H(18)	0.0292	0.9671	0.3275	0.169*
H(19)	−0.0571	0.8553	0.3595	0.169*
H(20)	0.1135	0.7345	0.3655	0.089*
H(21)	0.1820	0.8313	0.3110	0.089*
H(22)	−0.0732	0.9572	−0.0057	0.070*
H(23)	−0.0688	0.8121	−0.0394	0.070*
H(24)	−0.2040	0.8857	−0.0407	0.070*
H(25)	0.7353	−0.0397	0.5123	0.079*
H(26)	0.7216	0.0145	0.4250	0.079*
H(27)	0.6436	0.0824	0.4879	0.079*
H(28)	0.5311	−0.2866	0.4054	0.081*
H(29)	0.6615	−0.2241	0.3824	0.081*
H(30)	0.6555	−0.2746	0.4693	0.081*
H(31)	0.4431	−0.0218	0.5244	0.089*
H(32)	0.4018	−0.1649	0.4939	0.089*
H(33)	0.5249	−0.1458	0.5580	0.089*
H(34)	0.3266	0.0605	0.2750	0.065*
H(35)	0.4863	0.0218	0.1567	0.064*
H(36)	0.2577	0.183	0.1489	0.081*
H(37)	0.3249	0.1425	0.0743	0.081*
H(38)	0.2566	0.0337	0.1211	0.081*
H(39)	0.7205	0.3946	0.1875	0.047*
H(40)	0.7522	0.3752	0.0262	0.074*
H(41)	0.8628	0.3996	0.0975	0.074*
H(42)	0.8434	0.1661	0.0372	0.079*
H(43)	0.8766	0.1775	0.1297	0.079*
H(44)	0.6893	0.0549	0.1255	0.056*
H(45)	0.6284	0.1176	0.0444	0.056*
H(46)	0.5975	0.7969	0.1281	0.074*
H(47)	0.5594	0.7241	0.0466	0.074*
H(48)	0.4673	0.7133	0.1134	0.074*

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)	0.95	C(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)	0.95	C(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)	0.95	C(223)—H(37)	0.95
C(112)—H(2)	0.95	C(223)—H(38)	0.95
C(112)—H(3)	0.95	C(231)—C(232)	1.492 (12)
C(113)—H(4)	0.95	C(231)—C(233)	1.527 (13)
C(113)—H(5)	0.95	C(231)—H(39)	0.95
C(113)—H(6)	0.95	C(233)—C(234)	1.538 (15)
C(114)—H(7)	0.95	C(233)—H(40)	0.95
C(114)—H(8)	0.95	C(233)—H(41)	0.95
C(114)—H(9)	0.95	C(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)	0.95	C(235)—H(44)	0.95
C(123)—H(12)	0.95	C(235)—H(45)	0.95
C(123)—H(13)	0.95	C(241)—H(46)	0.95
C(123)—H(14)	0.95	C(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)	118.6	H(23)—C(141)—H(24)	109.5
C(121)—N(121)—H(10)	118.5	H(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)	120.0	C(213)—C(211)—C(214)	109.5 (9)
C(221)—N(221)—H(34)	119.9	C(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)	109.5	H(28)—C(213)—C(211)	109.5
H(1)—C(112)—H(3)	109.5	H(29)—C(213)—H(30)	109.5
H(1)—C(112)—C(111)	109.5	H(29)—C(213)—C(211)	109.5
H(2)—C(112)—H(3)	109.5	H(30)—C(213)—C(211)	109.5
H(2)—C(112)—C(111)	109.5	H(31)—C(214)—H(32)	109.5
H(3)—C(112)—C(111)	109.5	H(31)—C(214)—H(33)	109.5
H(4)—C(113)—H(5)	109.5	H(31)—C(214)—C(211)	109.5
H(4)—C(113)—H(6)	109.5	H(32)—C(214)—H(33)	109.5
H(4)—C(113)—C(111)	109.4	H(32)—C(214)—C(211)	109.5
H(5)—C(113)—H(6)	109.5	H(33)—C(214)—C(211)	109.5
H(5)—C(113)—C(111)	109.5	O(211)—C(215)—O(212)	124.9 (8)
H(6)—C(113)—C(111)	109.5	O(211)—C(215)—N(221)	111.7 (8)
H(7)—C(114)—H(8)	109.5	O(212)—C(215)—N(221)	123.4 (8)
H(7)—C(114)—H(9)	109.5	C(222)—C(221)—C(223)	108.1 (8)
H(7)—C(114)—C(111)	109.5	C(222)—C(221)—H(35)	109.1
H(8)—C(114)—H(9)	109.5	C(222)—C(221)—N(221)	111.4 (7)
H(8)—C(114)—C(111)	109.5	C(223)—C(221)—H(35)	109.1
H(9)—C(114)—C(111)	109.4	C(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)	109.3	H(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)	109.3	H(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)	109.3	H(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)	109.5	C(232)—C(231)—N(231)	112.7 (7)
H(12)—C(123)—H(14)	109.5	C(233)—C(231)—H(39)	109.4
H(12)—C(123)—C(121)	109.5	C(233)—C(231)—N(231)	104.4 (7)
H(13)—C(123)—H(14)	109.5	H(39)—C(231)—N(231)	109.4
H(13)—C(123)—C(121)	109.4	O(231)—C(232)—O(241)	124.5 (9)
H(14)—C(123)—C(121)	109.5	O(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)	110.8	C(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)	110.9	C(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)	110.7	H(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)	109.7	C(235)—C(234)—C(233)	104.2 (8)
C(134)—C(133)—H(17)	109.5	H(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)	109.5	H(43)—C(234)—C(233)	110.8
H(16)—C(133)—C(131)	109.6	H(44)—C(235)—H(45)	109.5
H(17)—C(133)—C(131)	109.5	H(44)—C(235)—N(231)	110.9
C(135)—C(134)—H(18)	109.3	H(44)—C(235)—C(234)	111.0
C(135)—C(134)—H(19)	109.4	H(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)	109.5	N(231)—C(235)—C(234)	103.3 (7)
H(18)—C(134)—C(133)	109.3	H(46)—C(241)—H(47)	109.5
H(19)—C(134)—C(133)	109.5	H(46)—C(241)—H(48)	109.5
H(20)—C(135)—H(21)	109.5	H(46)—C(241)—O(241)	109.5
H(20)—C(135)—N(131)	110.5	H(47)—C(241)—H(48)	109.5
H(20)—C(135)—C(134)	110.5	H(47)—C(241)—O(241)	109.4
H(21)—C(135)—N(131)	110.7	H(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—N121	168.1 (6)	N131—C131—C132—O141	168.7 (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—C131	175.4 (7)	C(133)—C(131)—C(132)—O(141)	−79.0 (9)
C(132)—O(141)—C(141)—H(22)	−60.0	H(15)—C(131)—C(132)—O(131)	−139.8
C(132)—O(141)—C(141)—H(23)	60.0	H(15)—C(131)—C(132)—O(141)	42.5
C(132)—O(141)—C(141)—H(24)	179.9	N(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—N221	−177.6 (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—C231	172.6 (6)	H(15)—C(131)—C(133)—H(16)	−128.8
C(232)—O(241)—C(241)—H(46)	179.8	H(15)—C(131)—C(133)—H(17)	−8.8
C(232)—O(241)—C(241)—H(47)	−60.0	C(131)—C(133)—C(134)—C(135)	14.3 (17)
C(232)—O(241)—C(241)—H(48)	59.8	C(131)—C(133)—C(134)—H(18)	134.2
C121—N121—C115—O111	−6.0 (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)	174.1	H(16)—C(133)—C(134)—H(18)	14.2
H(10)—N(121)—C(115)—O(112)	−7.6	H(16)—C(133)—C(134)—H(19)	134.2
C115—N121—C121—C122	−60.4 (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)	60.4	H(17)—C(133)—C(134)—H(19)	14.0
H(10)—N(121)—C(121)—C(122)	119.6	C(133)—C(134)—C(135)—N(131)	−15.9 (16)
H(10)—N(121)—C(121)—C(123)	−0.5	C(133)—C(134)—C(135)—H(20)	−135.1
H(10)—N(121)—C(121)—H(11)	−119.6	C(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—C121	173.0 (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—C132	−71.1 (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)	55.2	O(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)	−121.3	C(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)	−45.3	C(213)—C(211)—C(212)—H(27)	−176.0
C(122)—N(131)—C(135)—H(21)	76.1	C(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)	131.0	C(214)—C(211)—C(212)—H(27)	−52.2
C(131)—N(131)—C(135)—H(21)	−107.6	O(211)—C(211)—C(213)—H(28)	−51.7
C221—N221—C215—O211	176.3 (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)	−3.6	C(212)—C(211)—C(213)—H(28)	−175.1
H(34)—N(221)—C(215)—O(212)	177.0	C(212)—C(211)—C(213)—H(29)	−55.0
C215—N221—C221—C222	−76.3 (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)	44.1	C(214)—C(211)—C(213)—H(29)	179.8
H(34)—N(221)—C(221)—C(222)	103.6	C(214)—C(211)—C(213)—H(30)	−60.3
H(34)—N(221)—C(221)—C(223)	−16.3	O(211)—C(211)—C(214)—H(31)	−60.2
H(34)—N(221)—C(221)—H(35)	−136.0	O(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—C221	172.0 (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—C232	−61.0 (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)	61.1	C(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—N231	140.3 (8)
C(235)—N(231)—C(231)—H(39)	−112.1	C(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)	−37.3	H(35)—C(221)—C(222)—O(221)	−163.1
C(222)—N(231)—C(235)—H(45)	84.6	H(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)	135.4	N(221)—C(221)—C(223)—H(37)	−179.9
C(231)—N(231)—C(235)—H(45)	−102.7	N(221)—C(221)—C(223)—H(38)	−60.1
O(111)—C(111)—C(112)—H(1)	−180.0	C(222)—C(221)—C(223)—H(36)	−61.7
O(111)—C(111)—C(112)—H(2)	−59.9	C(222)—C(221)—C(223)—H(37)	58.2
O(111)—C(111)—C(112)—H(3)	60.1	C(222)—C(221)—C(223)—H(38)	178.0
C(113)—C(111)—C(112)—H(1)	−54.6	H(35)—C(221)—C(223)—H(36)	179.8
C(113)—C(111)—C(112)—H(2)	65.5	H(35)—C(221)—C(223)—H(37)	−60.3
C(113)—C(111)—C(112)—H(3)	−174.5	H(35)—C(221)—C(223)—H(38)	59.5
C(114)—C(111)—C(112)—H(1)	67.5	N(231)—C(231)—C(232)—O(231)	−30.9 (12)
C(114)—C(111)—C(112)—H(2)	−172.4	N231—C231—C232—O241	153.3 (7)
C(114)—C(111)—C(112)—H(3)	−52.4	C(233)—C(231)—C(232)—O(231)	85.9 (11)
O(111)—C(111)—C(113)—H(4)	−171.3	C(233)—C(231)—C(232)—O(241)	−89.8 (8)
O(111)—C(111)—C(113)—H(5)	−51.4	H(39)—C(231)—C(232)—O(231)	−153.0
O(111)—C(111)—C(113)—H(6)	68.7	H(39)—C(231)—C(232)—O(241)	31.4
C(112)—C(111)—C(113)—H(4)	64.4	N(231)—C(231)—C(233)—C(234)	−24.0 (8)
C(112)—C(111)—C(113)—H(5)	−175.7	N(231)—C(231)—C(233)—H(40)	95.1
C(112)—C(111)—C(113)—H(6)	−55.6	N(231)—C(231)—C(233)—H(41)	−143.0
C(114)—C(111)—C(113)—H(4)	−59.8	C(232)—C(231)—C(233)—C(234)	−145.9 (7)
C(114)—C(111)—C(113)—H(5)	59.8	C(232)—C(231)—C(233)—H(40)	−26.8
C(114)—C(111)—C(113)—H(6)	−179.8	C(232)—C(231)—C(233)—H(41)	95.1
O(111)—C(111)—C(114)—H(7)	−59.9	H(39)—C(231)—C(233)—C(234)	93.0
O(111)—C(111)—C(114)—H(8)	60.1	H(39)—C(231)—C(233)—H(40)	−147.9
O(111)—C(111)—C(114)—H(9)	−179.8	H(39)—C(231)—C(233)—H(41)	−26.0
C(112)—C(111)—C(114)—H(7)	57.8	C(231)—C(233)—C(234)—C(235)	34.2 (9)
C(112)—C(111)—C(114)—H(8)	177.9	C(231)—C(233)—C(234)—H(42)	153.3
C(112)—C(111)—C(114)—H(9)	−62.0	C(231)—C(233)—C(234)—H(43)	−85.0
C(113)—C(111)—C(114)—H(7)	−178.4	H(40)—C(233)—C(234)—C(235)	−84.9
C(113)—C(111)—C(114)—H(8)	−58.3	H(40)—C(233)—C(234)—H(42)	34.2
C(113)—C(111)—C(114)—H(9)	61.8	H(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—N131	153.2 (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)	−153.3	C(233)—C(234)—C(235)—H(44)	−149.7
H(11)—C(121)—C(122)—N(131)	32.3	C(233)—C(234)—C(235)—H(45)	88.3
N(121)—C(121)—C(123)—H(12)	−58.6	H(42)—C(234)—C(235)—N(231)	−149.9
N(121)—C(121)—C(123)—H(13)	61.3	H(42)—C(234)—C(235)—H(44)	91.1
N(121)—C(121)—C(123)—H(14)	−178.7	H(42)—C(234)—C(235)—H(45)	−30.5
C(122)—C(121)—C(123)—H(12)	180.0	H(43)—C(234)—C(235)—N(231)	88.5
C(122)—C(121)—C(123)—H(13)	−60.1	H(43)—C(234)—C(235)—H(44)	−30.5
C(122)—C(121)—C(123)—H(14)	59.8	H(43)—C(234)—C(235)—H(45)	−152.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N121—H10···O221	0.95	1.86	2.794 (12)	168
N221—H34···O112	0.95	2.21	3.070 (11)	150

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