N—H...O=C hydrogen bonding and O...O=C repulsive interactions in tert-butoxy­carbonyl-L-leucyl-L-alanine ethyl ester (Boc-L-Leu-L-Ala-OEt)

The crystal structure of the title compound, C₁₆H₃₀N₂O₅, has been determined. In the asymmetric unit, there are three independent mol­ecules which adopt extended β-sheet conformations. These mol­ecules are linked together into an infinite column by six hydrogen bonds of the type –NH...O=C. All the ester C=O groups are perpendicular to the column axis. This orientation probably reflects a repulsive force between two electronegative O atoms, viz. O...O=C.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.067
• wR factor = 0.159
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ..... =         32

Author Response: Because of the limited numbers of observed reflections. Even at the low temperature condition (173 K), diffractions from the crystal of (I) were too weak to collect enough numbers. Therefore only main-cain atoms were refefined anisotropically.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.54 Ratio

Author Response: It is due to the difference of thermal mobility. The atoms located at chain-ends and amino-acid side chains often show higer U(eq) compared with the atoms located inside of the molecule.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio

Author Response: It is due to the difference of thermal mobility. The atoms located at chain-ends and amino-acid side chains often show higer U(eq) compared with the atoms located inside of the molecule.

PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio

Author Response: It is due to the difference of thermal mobility. The atoms located at chain-ends and amino-acid side chains often show higer U(eq) compared with the atoms located inside of the molecule.

PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio

Author Response: It is due to the difference of thermal mobility. The atoms located at chain-ends and amino-acid side chains often show higer U(eq) compared with the atoms located inside of the molecule.

PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C211

Author Response: It is due to the difference of thermal mobility. The chain end atoms (C212, C213, and C214) often show higer U(eq) compared with the atoms (such as C211) located inside of the chain.

PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C224

Author Response: It is due to the difference of thermal mobility. The chain end atoms (C212, C213, and C214) often show higer U(eq) compared with the atoms (such as C211) located inside of the chain.

PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C311

Author Response: It is due to the difference of thermal mobility. The chain end atoms (C212, C213, and C214) often show higer U(eq) compared with the atoms (such as C211) located inside of the chain.

PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C324

Author Response: It is due to the difference of thermal mobility. The chain end atoms (C212, C213, and C214) often show higer U(eq) compared with the atoms (such as C211) located inside of the chain.

PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Author Response: The chain end atoms (-OEt) often show lower bond precision due to their higher thermal mobility compared with the atoms located inside of the chain.

PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C341   -   C342     =       1.43 Ang.

Author Response: The short bond length is attributable to the to their higher thermal mobility compared with the atoms located inside of the chain.

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           68.25
           From the CIF: _reflns_number_total               5906
           Count of symmetry unique reflns         5906
           Completeness (_total/calc)            100.00%
           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

Author Response: The absolute stereochemistry was not established from the diffraction experiment. All the Friedel pairs are averaged. The absolute configuration was confirmed from the analytical data. The explanation has been added into the text.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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-leucyl-L-alanine ethyl ester

Crystal data

C16H30N2O5	Dx = 1.131 Mg m^−3
Mr = 330.42	Melting point: 391 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11533 reflections
a = 11.322 (6) Å	θ = 5.6–67.8°
b = 19.903 (9) Å	µ = 0.69 mm^−1
c = 25.828 (16) Å	T = 173 K
V = 5820 (5) Å^3	Platelet, colorless
Z = 12	0.30 × 0.20 × 0.20 mm
F(000) = 2160.00

Data collection

Rigaku R-AXIS RAPID diffractometer	4827 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.056
ω scans	θmax = 68.3°
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	h = −13→13
Tmin = 0.848, Tmax = 0.872	k = −23→23
105756 measured reflections	l = −30→31
5906 independent reflections

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[0.001Fo^2 + 3σ(Fo^2) + 0.5]/(4Fo^2)
wR(F^2) = 0.159	(Δ/σ)max = 0.006
S = 1.43	Δρmax = 0.58 e Å^−3
5906 reflections	Δρmin = −0.38 e Å^−3
552 parameters

Special details

Experimental. ? #Insert any special details here.

Refinement. Refinement using all reflections. 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 (Ų)

	x	y	z	Uiso*/Ueq
O(111)	0.1269 (3)	0.5795 (1)	0.0946 (1)	0.052 (1)
O(112)	0.1503 (3)	0.5494 (2)	0.0112 (1)	0.055 (1)
O(121)	0.2824 (3)	0.3492 (1)	0.0897 (1)	0.0419 (9)
O(131)	0.4573 (3)	0.2560 (2)	0.0199 (1)	0.054 (1)
O(141)	0.3268 (3)	0.1765 (1)	0.0407 (1)	0.053 (1)
O(211)	0.0722 (3)	0.3977 (2)	0.1905 (1)	0.048 (1)
O(212)	0.1607 (3)	0.4480 (2)	0.2585 (1)	0.048 (1)
O(221)	0.3563 (3)	0.5180 (2)	0.1747 (1)	0.046 (1)
O(231)	0.6439 (4)	0.5417 (2)	0.1677 (2)	0.083 (1)
O(241)	0.5542 (4)	0.6412 (2)	0.1594 (1)	0.068 (1)
O(311)	0.5899 (3)	0.4289 (2)	0.4172 (1)	0.047 (1)
O(312)	0.5263 (3)	0.4389 (2)	0.3349 (1)	0.048 (1)
O(321)	0.2847 (3)	0.5814 (1)	0.4058 (1)	0.048 (1)
O(331)	−0.0019 (4)	0.5915 (2)	0.3486 (2)	0.073 (1)
O(341)	0.0409 (3)	0.7010 (2)	0.3492 (1)	0.063 (1)
N(121)	0.2356 (4)	0.4916 (2)	0.0756 (1)	0.040 (1)
N(131)	0.2691 (3)	0.3447 (2)	0.0036 (1)	0.035 (1)
N(221)	0.2644 (3)	0.3928 (2)	0.1976 (1)	0.036 (1)
N(231)	0.4733 (4)	0.5146 (2)	0.2442 (1)	0.047 (1)
N(321)	0.4070 (3)	0.4581 (2)	0.4033 (1)	0.035 (1)
N(331)	0.2293 (4)	0.5626 (2)	0.3240 (1)	0.044 (1)
C(111)	0.0580 (5)	0.6387 (3)	0.0827 (2)	0.056 (2)
C(112)	−0.0554 (6)	0.6180 (3)	0.0585 (3)	0.080 (2)*
C(113)	0.1263 (6)	0.6870 (3)	0.0493 (3)	0.084 (2)*
C(114)	0.0355 (6)	0.6683 (3)	0.1353 (2)	0.069 (2)*
C(115)	0.1702 (4)	0.5407 (2)	0.0568 (2)	0.038 (1)
C(121)	0.3116 (4)	0.4522 (2)	0.0427 (2)	0.036 (1)
C(122)	0.2848 (4)	0.3772 (2)	0.0480 (1)	0.032 (1)
C(123)	0.4393 (4)	0.4668 (2)	0.0563 (2)	0.040 (1)*
C(124)	0.5323 (4)	0.4251 (2)	0.0308 (2)	0.046 (1)*
C(125)	0.6507 (5)	0.4419 (3)	0.0542 (2)	0.062 (1)*
C(126)	0.5341 (6)	0.4334 (3)	−0.0274 (2)	0.068 (2)*
C(131)	0.2533 (4)	0.2731 (2)	0.0021 (2)	0.036 (1)
C(132)	0.3580 (4)	0.2370 (2)	0.0225 (2)	0.041 (1)
C(133)	0.2327 (5)	0.2515 (2)	−0.0532 (2)	0.047 (1)*
C(141)	0.4238 (6)	0.1317 (3)	0.0539 (2)	0.067 (2)*
C(142)	0.4703 (7)	0.0964 (3)	0.0088 (2)	0.080 (2)*
C(211)	−0.0469 (5)	0.4179 (3)	0.2029 (2)	0.054 (2)
C(212)	−0.1174 (6)	0.3915 (3)	0.1597 (2)	0.082 (2)*
C(213)	−0.0538 (8)	0.4933 (3)	0.2044 (3)	0.101 (2)*
C(214)	−0.0837 (7)	0.3861 (4)	0.2522 (3)	0.099 (2)*
C(215)	0.1657 (4)	0.4165 (2)	0.2187 (2)	0.039 (1)
C(221)	0.3768 (4)	0.4126 (2)	0.2184 (2)	0.037 (1)
C(222)	0.3985 (4)	0.4860 (2)	0.2105 (2)	0.038 (1)
C(223)	0.4744 (4)	0.3723 (2)	0.1926 (2)	0.038 (1)*
C(224)	0.4786 (4)	0.2985 (2)	0.2060 (2)	0.042 (1)*
C(225)	0.5281 (6)	0.2869 (3)	0.2593 (2)	0.069 (2)*
C(226)	0.5526 (6)	0.2617 (3)	0.1675 (2)	0.071 (2)*
C(231)	0.5181 (5)	0.5811 (2)	0.2354 (2)	0.048 (1)*
C(232)	0.5797 (5)	0.5847 (3)	0.1845 (2)	0.055 (1)*
C(233)	0.6012 (6)	0.6002 (3)	0.2780 (2)	0.076 (2)*
C(241)	0.6105 (7)	0.6499 (4)	0.1097 (3)	0.088 (2)*
C(242)	0.5477 (9)	0.7042 (4)	0.0830 (3)	0.130 (3)*
C(311)	0.7115 (4)	0.4116 (3)	0.4028 (2)	0.048 (1)
C(312)	0.7685 (6)	0.4691 (3)	0.3755 (2)	0.070 (2)*
C(313)	0.7167 (6)	0.3481 (3)	0.3717 (2)	0.070 (2)*
C(314)	0.7667 (6)	0.4007 (3)	0.4555 (2)	0.072 (2)*
C(315)	0.5084 (4)	0.4417 (2)	0.3810 (2)	0.038 (1)
C(321)	0.3002 (4)	0.4690 (2)	0.3736 (2)	0.035 (1)
C(322)	0.2727 (4)	0.5430 (2)	0.3696 (2)	0.035 (1)
C(323)	0.1966 (4)	0.4342 (2)	0.3993 (2)	0.044 (1)*
C(324)	0.2106 (5)	0.3582 (2)	0.4049 (2)	0.053 (1)*
C(325)	0.2097 (6)	0.3235 (3)	0.3540 (2)	0.082 (2)*
C(326)	0.1168 (6)	0.3322 (3)	0.4402 (3)	0.082 (2)*
C(331)	0.1822 (5)	0.6287 (2)	0.3164 (2)	0.044 (1)
C(332)	0.0646 (5)	0.6365 (3)	0.3405 (2)	0.048 (2)
C(333)	0.1778 (6)	0.6455 (3)	0.2598 (2)	0.065 (2)*
C(341)	−0.0734 (6)	0.7173 (3)	0.3710 (3)	0.076 (2)*
C(342)	−0.1610 (7)	0.7183 (4)	0.3312 (3)	0.101 (2)*
H(1)	−0.1014	0.6566	0.0505	0.097*
H(2)	−0.0392	0.5939	0.0275	0.096*
H(3)	−0.0979	0.5900	0.0817	0.096*
H(4)	0.1962	0.7009	0.0665	0.101*
H(5)	0.1465	0.6654	0.0177	0.101*
H(6)	0.0785	0.7252	0.0421	0.101*
H(7)	0.1090	0.6788	0.1510	0.083*
H(8)	−0.0097	0.7082	0.1314	0.083*
H(9)	−0.0064	0.6374	0.1565	0.083*
H(10)	0.2336	0.4825	0.1117	0.049*
H(11)	0.2978	0.4652	0.0078	0.043*
H(12)	0.4548	0.5123	0.0474	0.048*
H(13)	0.4476	0.4611	0.0926	0.048*
H(14)	0.5156	0.3793	0.0381	0.056*
H(15)	0.6483	0.4351	0.0906	0.074*
H(16)	0.7096	0.4139	0.0394	0.074*
H(17)	0.6690	0.4876	0.0471	0.074*
H(18)	0.5504	0.4790	−0.0355	0.081*
H(19)	0.5936	0.4055	−0.0420	0.082*
H(20)	0.4594	0.4213	−0.0414	0.082*
H(21)	0.2682	0.3696	−0.0278	0.042*
H(22)	0.1864	0.2612	0.0224	0.044*
H(23)	0.1647	0.2734	−0.0665	0.056*
H(24)	0.2996	0.2632	−0.0735	0.056*
H(25)	0.2214	0.2042	−0.0544	0.056*
H(26)	0.4857	0.1574	0.0689	0.081*
H(27)	0.3964	0.0996	0.0784	0.081*
H(28)	0.4085	0.0708	−0.0063	0.096*
H(29)	0.4988	0.1283	−0.0155	0.096*
H(30)	0.5329	0.0673	0.0187	0.096*
H(31)	−0.1979	0.4030	0.1648	0.099*
H(32)	−0.0904	0.4102	0.1280	0.099*
H(33)	−0.1096	0.3440	0.1586	0.099*
H(34)	−0.0019	0.5083	0.2309	0.122*
H(35)	−0.0307	0.5125	0.1723	0.121*
H(36)	−0.1322	0.5068	0.2124	0.122*
H(37)	−0.1620	0.3998	0.2602	0.119*
H(38)	−0.0809	0.3385	0.2496	0.118*
H(39)	−0.0317	0.4006	0.2789	0.118*
H(40)	0.2609	0.3630	0.1689	0.044*
H(41)	0.3772	0.4030	0.2544	0.044*
H(42)	0.4643	0.3764	0.1562	0.046*
H(43)	0.5478	0.3916	0.2024	0.046*
H(44)	0.4005	0.2811	0.2048	0.051*
H(45)	0.5298	0.2402	0.2671	0.084*
H(46)	0.6060	0.3045	0.2609	0.083*
H(47)	0.4795	0.3094	0.2838	0.083*
H(48)	0.5538	0.2153	0.1761	0.085*
H(49)	0.5204	0.2673	0.1338	0.085*
H(50)	0.6308	0.2789	0.1683	0.085*
H(51)	0.4978	0.4905	0.2741	0.057*
H(52)	0.4541	0.6120	0.2352	0.057*
H(53)	0.6650	0.5693	0.2781	0.091*
H(54)	0.6306	0.6443	0.2725	0.091*
H(55)	0.5613	0.5985	0.3103	0.090*
H(56)	0.6909	0.6620	0.1147	0.106*
H(57)	0.6063	0.6094	0.0903	0.106*
H(58)	0.5524	0.7443	0.1028	0.156*
H(59)	0.5825	0.7113	0.0500	0.156*
H(60)	0.4673	0.6918	0.0788	0.156*
H(61)	0.8470	0.4575	0.3661	0.084*
H(62)	0.7248	0.4800	0.3453	0.084*
H(63)	0.7699	0.5067	0.3982	0.084*
H(64)	0.6840	0.3120	0.3911	0.083*
H(65)	0.6721	0.3543	0.3409	0.084*
H(66)	0.7962	0.3379	0.3630	0.083*
H(67)	0.7272	0.3658	0.4737	0.086*
H(68)	0.8475	0.3891	0.4511	0.086*
H(69)	0.7609	0.4413	0.4746	0.086*
H(70)	0.4044	0.4633	0.4398	0.042*
H(71)	0.3109	0.4513	0.3398	0.042*
H(72)	0.1848	0.4535	0.4325	0.052*
H(73)	0.1284	0.4415	0.3786	0.052*
H(74)	0.2845	0.3504	0.4213	0.064*
H(75)	0.1363	0.3311	0.3371	0.099*
H(76)	0.2719	0.3409	0.3333	0.099*
H(77)	0.2209	0.2767	0.3589	0.099*
H(78)	0.1192	0.3541	0.4728	0.099*
H(79)	0.0423	0.3399	0.4244	0.099*
H(80)	0.1281	0.2853	0.4449	0.099*
H(81)	0.2290	0.5322	0.2957	0.052*
H(82)	0.2344	0.6597	0.3325	0.053*
H(83)	0.2546	0.6416	0.2453	0.078*
H(84)	0.1260	0.6148	0.2431	0.078*
H(85)	0.1496	0.6900	0.2550	0.078*
H(86)	−0.0937	0.6847	0.3964	0.091*
H(87)	−0.0689	0.7603	0.3867	0.091*
H(88)	−0.2356	0.7291	0.3458	0.121*
H(89)	−0.1408	0.7511	0.3059	0.121*
H(90)	−0.1650	0.6753	0.3153	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(111)	0.069 (2)	0.049 (2)	0.037 (2)	0.031 (2)	−0.003 (2)	−0.007 (2)
O(112)	0.066 (2)	0.064 (2)	0.035 (2)	0.028 (2)	−0.011 (2)	−0.006 (2)
O(121)	0.052 (2)	0.046 (2)	0.028 (2)	−0.001 (2)	0.000 (2)	0.001 (1)
O(131)	0.040 (2)	0.042 (2)	0.080 (3)	−0.005 (2)	−0.011 (2)	0.005 (2)
O(141)	0.051 (2)	0.038 (2)	0.069 (2)	−0.006 (2)	−0.006 (2)	0.014 (2)
O(211)	0.031 (2)	0.071 (2)	0.041 (2)	0.003 (2)	−0.004 (2)	−0.018 (2)
O(212)	0.047 (2)	0.065 (2)	0.033 (2)	0.006 (2)	−0.001 (2)	−0.019 (2)
O(221)	0.057 (2)	0.046 (2)	0.035 (2)	0.002 (2)	−0.013 (2)	−0.001 (1)
O(231)	0.068 (3)	0.071 (3)	0.112 (3)	0.009 (2)	0.023 (3)	−0.011 (2)
O(241)	0.080 (3)	0.056 (2)	0.068 (2)	−0.011 (2)	0.014 (2)	0.000 (2)
O(311)	0.033 (2)	0.073 (2)	0.033 (2)	0.007 (2)	−0.002 (1)	−0.000 (2)
O(312)	0.044 (2)	0.075 (2)	0.026 (2)	0.007 (2)	0.002 (1)	−0.001 (2)
O(321)	0.064 (2)	0.044 (2)	0.037 (2)	0.000 (2)	−0.008 (2)	−0.010 (2)
O(331)	0.060 (3)	0.053 (2)	0.106 (3)	0.000 (2)	0.019 (2)	0.007 (2)
O(341)	0.054 (2)	0.056 (2)	0.079 (3)	0.010 (2)	0.011 (2)	−0.013 (2)
N(121)	0.051 (2)	0.039 (2)	0.031 (2)	0.018 (2)	0.002 (2)	0.001 (2)
N(131)	0.041 (2)	0.034 (2)	0.029 (2)	0.002 (2)	0.002 (2)	0.002 (2)
N(221)	0.031 (2)	0.046 (2)	0.032 (2)	0.002 (2)	−0.001 (2)	−0.009 (2)
N(231)	0.053 (3)	0.045 (2)	0.044 (2)	−0.001 (2)	−0.012 (2)	−0.003 (2)
N(321)	0.028 (2)	0.050 (2)	0.028 (2)	0.004 (2)	−0.001 (2)	−0.007 (2)
N(331)	0.055 (2)	0.043 (2)	0.033 (2)	0.015 (2)	−0.005 (2)	−0.006 (2)
C(111)	0.070 (4)	0.057 (3)	0.042 (3)	0.036 (3)	−0.004 (3)	−0.003 (2)
C(115)	0.045 (3)	0.037 (2)	0.032 (3)	0.006 (2)	−0.002 (2)	−0.005 (2)
C(121)	0.048 (3)	0.033 (2)	0.028 (2)	0.008 (2)	0.000 (2)	−0.001 (2)
C(122)	0.029 (2)	0.042 (2)	0.026 (2)	0.006 (2)	0.002 (2)	0.001 (2)
C(131)	0.030 (2)	0.047 (3)	0.031 (2)	−0.004 (2)	0.001 (2)	−0.003 (2)
C(132)	0.042 (3)	0.038 (3)	0.042 (3)	−0.007 (2)	−0.003 (2)	0.000 (2)
C(211)	0.038 (3)	0.069 (4)	0.054 (3)	0.007 (3)	−0.004 (3)	−0.007 (3)
C(215)	0.036 (3)	0.049 (3)	0.032 (3)	0.002 (2)	−0.002 (2)	0.001 (2)
C(221)	0.039 (3)	0.044 (3)	0.027 (2)	0.001 (2)	−0.006 (2)	−0.002 (2)
C(222)	0.036 (3)	0.044 (3)	0.035 (3)	0.002 (2)	−0.003 (2)	−0.007 (2)
C(311)	0.034 (3)	0.067 (3)	0.043 (3)	0.007 (2)	−0.003 (2)	−0.009 (2)
C(315)	0.039 (3)	0.043 (3)	0.033 (3)	0.002 (2)	−0.006 (2)	−0.001 (2)
C(321)	0.036 (3)	0.042 (3)	0.026 (2)	0.003 (2)	−0.005 (2)	−0.004 (2)
C(322)	0.033 (2)	0.042 (3)	0.031 (2)	0.001 (2)	−0.002 (2)	−0.004 (2)
C(331)	0.051 (3)	0.042 (3)	0.040 (3)	0.011 (2)	−0.010 (2)	0.001 (2)
C(332)	0.052 (3)	0.047 (3)	0.044 (3)	0.006 (3)	−0.002 (3)	0.000 (2)

Geometric parameters (Å, º)

O(111)—C(111)	1.445 (6)	C(211)—C(212)	1.469 (8)
O(111)—C(115)	1.337 (5)	C(211)—C(213)	1.503 (9)
O(112)—C(115)	1.213 (5)	C(211)—C(214)	1.483 (9)
O(121)—C(122)	1.215 (5)	C(212)—H(31)	0.950
O(131)—C(132)	1.187 (6)	C(212)—H(32)	0.950
O(141)—C(132)	1.341 (6)	C(212)—H(33)	0.950
O(141)—C(141)	1.456 (7)	C(213)—H(34)	0.950
O(211)—C(211)	1.443 (6)	C(213)—H(35)	0.950
O(211)—C(215)	1.337 (6)	C(213)—H(36)	0.950
O(212)—C(215)	1.205 (5)	C(214)—H(37)	0.950
O(221)—C(222)	1.221 (5)	C(214)—H(38)	0.950
O(231)—C(232)	1.205 (7)	C(214)—H(39)	0.950
O(241)—C(232)	1.330 (7)	C(221)—C(222)	1.495 (6)
O(241)—C(241)	1.444 (8)	C(221)—C(223)	1.519 (6)
O(311)—C(311)	1.467 (6)	C(221)—H(41)	0.950
O(311)—C(315)	1.338 (5)	C(223)—C(224)	1.509 (6)
O(312)—C(315)	1.208 (5)	C(223)—H(42)	0.950
O(321)—C(322)	1.216 (5)	C(223)—H(43)	0.950
O(331)—C(332)	1.188 (7)	C(224)—C(225)	1.506 (7)
O(341)—C(332)	1.330 (6)	C(224)—C(226)	1.492 (8)
O(341)—C(341)	1.449 (7)	C(224)—H(44)	0.950
N(121)—C(115)	1.318 (6)	C(225)—H(45)	0.950
N(121)—C(121)	1.442 (6)	C(225)—H(46)	0.950
N(121)—H(10)	0.950	C(225)—H(47)	0.950
N(131)—C(122)	1.328 (5)	C(226)—H(48)	0.950
N(131)—C(131)	1.438 (6)	C(226)—H(49)	0.950
N(131)—H(21)	0.950	C(226)—H(50)	0.950
N(221)—C(215)	1.330 (6)	C(231)—C(232)	1.489 (7)
N(221)—C(221)	1.436 (6)	C(231)—C(233)	1.496 (8)
N(221)—H(40)	0.950	C(231)—H(52)	0.950
N(231)—C(222)	1.341 (6)	C(233)—H(53)	0.950
N(231)—C(231)	1.435 (6)	C(233)—H(54)	0.950
N(231)—H(51)	0.950	C(233)—H(55)	0.950
N(321)—C(315)	1.325 (6)	C(241)—C(242)	1.466 (12)
N(321)—C(321)	1.448 (5)	C(241)—H(56)	0.950
N(321)—H(70)	0.950	C(241)—H(57)	0.950
N(331)—C(322)	1.335 (6)	C(242)—H(58)	0.950
N(331)—C(331)	1.432 (6)	C(242)—H(59)	0.950
N(331)—H(81)	0.950	C(242)—H(60)	0.950
C(111)—C(112)	1.487 (9)	C(311)—C(312)	1.491 (8)
C(111)—C(113)	1.506 (9)	C(311)—C(313)	1.499 (8)
C(111)—C(114)	1.501 (7)	C(311)—C(314)	1.511 (8)
C(112)—H(1)	0.950	C(312)—H(61)	0.950
C(112)—H(2)	0.950	C(312)—H(62)	0.950
C(112)—H(3)	0.950	C(312)—H(63)	0.950
C(113)—H(4)	0.950	C(313)—H(64)	0.950
C(113)—H(5)	0.950	C(313)—H(65)	0.950
C(113)—H(6)	0.950	C(313)—H(66)	0.950
C(114)—H(7)	0.950	C(314)—H(67)	0.950
C(114)—H(8)	0.950	C(314)—H(68)	0.950
C(114)—H(9)	0.950	C(314)—H(69)	0.950
C(121)—C(122)	1.530 (6)	C(321)—C(322)	1.507 (6)
C(121)—C(123)	1.516 (6)	C(321)—C(323)	1.516 (6)
C(121)—H(11)	0.950	C(321)—H(71)	0.950
C(123)—C(124)	1.493 (7)	C(323)—C(324)	1.528 (6)
C(123)—H(12)	0.950	C(323)—H(72)	0.950
C(123)—H(13)	0.950	C(323)—H(73)	0.950
C(124)—C(125)	1.508 (7)	C(324)—C(325)	1.485 (8)
C(124)—C(126)	1.512 (7)	C(324)—C(326)	1.491 (8)
C(124)—H(14)	0.950	C(324)—H(74)	0.950
C(125)—H(15)	0.950	C(325)—H(75)	0.950
C(125)—H(16)	0.950	C(325)—H(76)	0.950
C(125)—H(17)	0.950	C(325)—H(77)	0.950
C(126)—H(18)	0.950	C(326)—H(78)	0.950
C(126)—H(19)	0.950	C(326)—H(79)	0.950
C(126)—H(20)	0.950	C(326)—H(80)	0.950
C(131)—C(132)	1.483 (7)	C(331)—C(332)	1.478 (7)
C(131)—C(133)	1.510 (6)	C(331)—C(333)	1.502 (7)
C(131)—H(22)	0.950	C(331)—H(82)	0.950
C(133)—H(23)	0.950	C(333)—H(83)	0.950
C(133)—H(24)	0.950	C(333)—H(84)	0.950
C(133)—H(25)	0.950	C(333)—H(85)	0.950
C(141)—C(142)	1.459 (9)	C(341)—C(342)	1.429 (11)
C(141)—H(26)	0.950	C(341)—H(86)	0.950
C(141)—H(27)	0.950	C(341)—H(87)	0.950
C(142)—H(28)	0.950	C(342)—H(88)	0.950
C(142)—H(29)	0.950	C(342)—H(89)	0.950
C(142)—H(30)	0.950	C(342)—H(90)	0.950
C(111)—O(111)—C(115)	120.9 (4)	H(41)—C(221)—N(221)	108.3
C(132)—O(141)—C(141)	115.7 (4)	O(221)—C(222)—N(231)	121.2 (4)
C(211)—O(211)—C(215)	122.8 (4)	O(221)—C(222)—C(221)	123.2 (4)
C(232)—O(241)—C(241)	116.1 (5)	N(231)—C(222)—C(221)	115.5 (4)
C(311)—O(311)—C(315)	121.1 (3)	C(224)—C(223)—H(42)	108.3
C(332)—O(341)—C(341)	117.4 (4)	C(224)—C(223)—H(43)	107.8
C(115)—N(121)—C(121)	121.4 (4)	C(224)—C(223)—C(221)	115.9 (4)
C(115)—N(121)—H(10)	119.3	H(42)—C(223)—H(43)	109.5
C(121)—N(121)—H(10)	119.2	H(42)—C(223)—C(221)	107.5
C(122)—N(131)—C(131)	121.4 (3)	H(43)—C(223)—C(221)	107.8
C(122)—N(131)—H(21)	119.0	C(225)—C(224)—C(226)	108.9 (4)
C(131)—N(131)—H(21)	119.7	C(225)—C(224)—H(44)	108.6
C(215)—N(221)—C(221)	119.6 (4)	C(225)—C(224)—C(223)	111.8 (4)
C(215)—N(221)—H(40)	120.4	C(226)—C(224)—H(44)	108.8
C(221)—N(221)—H(40)	120.0	C(226)—C(224)—C(223)	110.1 (4)
C(222)—N(231)—C(231)	120.8 (4)	H(44)—C(224)—C(223)	108.6
C(222)—N(231)—H(51)	119.7	H(45)—C(225)—H(46)	109.5
C(231)—N(231)—H(51)	119.5	H(45)—C(225)—H(47)	109.5
C(315)—N(321)—C(321)	122.1 (4)	H(45)—C(225)—C(224)	110.5
C(315)—N(321)—H(70)	119.0	H(46)—C(225)—H(47)	109.5
C(321)—N(321)—H(70)	118.9	H(46)—C(225)—C(224)	109.2
C(322)—N(331)—C(331)	121.8 (4)	H(47)—C(225)—C(224)	108.7
C(322)—N(331)—H(81)	119.6	H(48)—C(226)—H(49)	109.5
C(331)—N(331)—H(81)	118.7	H(48)—C(226)—H(50)	109.5
C(112)—C(111)—C(113)	112.2 (5)	H(48)—C(226)—C(224)	109.3
C(112)—C(111)—C(114)	110.0 (5)	H(49)—C(226)—H(50)	109.5
C(112)—C(111)—O(111)	109.2 (4)	H(49)—C(226)—C(224)	109.7
C(113)—C(111)—C(114)	110.8 (5)	H(50)—C(226)—C(224)	109.4
C(113)—C(111)—O(111)	111.4 (5)	C(232)—C(231)—C(233)	110.0 (5)
C(114)—C(111)—O(111)	102.7 (4)	C(232)—C(231)—H(52)	108.8
H(1)—C(112)—H(2)	109.5	C(232)—C(231)—N(231)	110.5 (4)
H(1)—C(112)—H(3)	109.5	C(233)—C(231)—H(52)	108.6
H(1)—C(112)—C(111)	109.9	C(233)—C(231)—N(231)	109.9 (4)
H(2)—C(112)—H(3)	109.5	H(52)—C(231)—N(231)	109.1
H(2)—C(112)—C(111)	109.1	O(231)—C(232)—O(241)	123.7 (5)
H(3)—C(112)—C(111)	109.4	O(231)—C(232)—C(231)	124.5 (5)
H(4)—C(113)—H(5)	109.5	O(241)—C(232)—C(231)	111.8 (5)
H(4)—C(113)—H(6)	109.5	H(53)—C(233)—H(54)	109.5
H(4)—C(113)—C(111)	110.2	H(53)—C(233)—H(55)	109.5
H(5)—C(113)—H(6)	109.5	H(53)—C(233)—C(231)	108.4
H(5)—C(113)—C(111)	109.0	H(54)—C(233)—H(55)	109.5
H(6)—C(113)—C(111)	109.2	H(54)—C(233)—C(231)	110.2
H(7)—C(114)—H(8)	109.5	H(55)—C(233)—C(231)	109.8
H(7)—C(114)—H(9)	109.5	C(242)—C(241)—H(56)	110.0
H(7)—C(114)—C(111)	108.9	C(242)—C(241)—H(57)	110.8
H(8)—C(114)—H(9)	109.5	C(242)—C(241)—O(241)	107.0 (6)
H(8)—C(114)—C(111)	108.9	H(56)—C(241)—H(57)	109.5
H(9)—C(114)—C(111)	110.6	H(56)—C(241)—O(241)	109.4
O(111)—C(115)—O(112)	124.0 (4)	H(57)—C(241)—O(241)	110.1
O(111)—C(115)—N(121)	111.5 (4)	H(58)—C(242)—H(59)	109.6
O(112)—C(115)—N(121)	124.6 (4)	H(58)—C(242)—H(60)	109.5
C(122)—C(121)—C(123)	110.8 (3)	H(58)—C(242)—C(241)	109.3
C(122)—C(121)—H(11)	108.5	H(59)—C(242)—H(60)	109.5
C(122)—C(121)—N(121)	111.1 (3)	H(59)—C(242)—C(241)	109.3
C(123)—C(121)—H(11)	108.9	H(60)—C(242)—C(241)	109.1
C(123)—C(121)—N(121)	109.2 (3)	C(312)—C(311)—C(313)	112.1 (4)
H(11)—C(121)—N(121)	108.3	C(312)—C(311)—C(314)	110.9 (5)
O(121)—C(122)—N(131)	122.8 (4)	C(312)—C(311)—O(311)	110.2 (4)
O(121)—C(122)—C(121)	122.1 (4)	C(313)—C(311)—C(314)	110.2 (4)
N(131)—C(122)—C(121)	115.1 (3)	C(313)—C(311)—O(311)	111.7 (4)
C(124)—C(123)—H(12)	107.1	C(314)—C(311)—O(311)	101.2 (4)
C(124)—C(123)—H(13)	107.4	H(61)—C(312)—H(62)	109.5
C(124)—C(123)—C(121)	117.6 (4)	H(61)—C(312)—H(63)	109.5
H(12)—C(123)—H(13)	109.5	H(61)—C(312)—C(311)	109.9
H(12)—C(123)—C(121)	107.7	H(62)—C(312)—H(63)	109.5
H(13)—C(123)—C(121)	107.4	H(62)—C(312)—C(311)	109.8
C(125)—C(124)—C(126)	111.2 (4)	H(63)—C(312)—C(311)	108.7
C(125)—C(124)—H(14)	108.0	H(64)—C(313)—H(65)	109.5
C(125)—C(124)—C(123)	109.1 (4)	H(64)—C(313)—H(66)	109.5
C(126)—C(124)—H(14)	107.8	H(64)—C(313)—C(311)	109.8
C(126)—C(124)—C(123)	112.8 (4)	H(65)—C(313)—H(66)	109.5
H(14)—C(124)—C(123)	107.8	H(65)—C(313)—C(311)	108.5
H(15)—C(125)—H(16)	109.5	H(66)—C(313)—C(311)	110.1
H(15)—C(125)—H(17)	109.5	H(67)—C(314)—H(68)	109.5
H(15)—C(125)—C(124)	109.8	H(67)—C(314)—H(69)	109.5
H(16)—C(125)—H(17)	109.5	H(67)—C(314)—C(311)	110.8
H(16)—C(125)—C(124)	109.4	H(68)—C(314)—H(69)	109.5
H(17)—C(125)—C(124)	109.1	H(68)—C(314)—C(311)	109.1
H(18)—C(126)—H(19)	109.5	H(69)—C(314)—C(311)	108.5
H(18)—C(126)—H(20)	109.5	O(311)—C(315)—O(312)	124.3 (4)
H(18)—C(126)—C(124)	108.9	O(311)—C(315)—N(321)	110.0 (4)
H(19)—C(126)—H(20)	109.5	O(312)—C(315)—N(321)	125.8 (4)
H(19)—C(126)—C(124)	109.8	C(322)—C(321)—C(323)	108.4 (4)
H(20)—C(126)—C(124)	109.7	C(322)—C(321)—H(71)	109.1
C(132)—C(131)—C(133)	108.7 (4)	C(322)—C(321)—N(321)	110.8 (3)
C(132)—C(131)—H(22)	108.8	C(323)—C(321)—H(71)	109.4
C(132)—C(131)—N(131)	111.9 (4)	C(323)—C(321)—N(321)	110.2 (3)
C(133)—C(131)—H(22)	109.0	H(71)—C(321)—N(321)	108.9
C(133)—C(131)—N(131)	109.0 (4)	O(321)—C(322)—N(331)	122.3 (4)
H(22)—C(131)—N(131)	109.4	O(321)—C(322)—C(321)	122.6 (4)
O(131)—C(132)—O(141)	123.7 (4)	N(331)—C(322)—C(321)	115.0 (4)
O(131)—C(132)—C(131)	125.7 (4)	C(324)—C(323)—H(72)	109.3
O(141)—C(132)—C(131)	110.4 (4)	C(324)—C(323)—H(73)	106.8
H(23)—C(133)—H(24)	109.5	C(324)—C(323)—C(321)	114.5 (4)
H(23)—C(133)—H(25)	109.5	H(72)—C(323)—H(73)	109.5
H(23)—C(133)—C(131)	109.7	H(72)—C(323)—C(321)	108.6
H(24)—C(133)—H(25)	109.5	H(73)—C(323)—C(321)	108.2
H(24)—C(133)—C(131)	109.2	C(325)—C(324)—C(326)	112.0 (5)
H(25)—C(133)—C(131)	109.5	C(325)—C(324)—H(74)	109.0
C(142)—C(141)—H(26)	108.5	C(325)—C(324)—C(323)	112.0 (4)
C(142)—C(141)—H(27)	109.0	C(326)—C(324)—H(74)	107.4
C(142)—C(141)—O(141)	112.3 (5)	C(326)—C(324)—C(323)	109.1 (4)
H(26)—C(141)—H(27)	109.5	H(74)—C(324)—C(323)	107.1
H(26)—C(141)—O(141)	108.7	H(75)—C(325)—H(76)	109.5
H(27)—C(141)—O(141)	108.8	H(75)—C(325)—H(77)	109.5
H(28)—C(142)—H(29)	109.5	H(75)—C(325)—C(324)	109.8
H(28)—C(142)—H(30)	109.5	H(76)—C(325)—H(77)	109.5
H(28)—C(142)—C(141)	108.7	H(76)—C(325)—C(324)	108.9
H(29)—C(142)—H(30)	109.5	H(77)—C(325)—C(324)	109.6
H(29)—C(142)—C(141)	109.3	H(78)—C(326)—H(79)	109.5
H(30)—C(142)—C(141)	110.4	H(78)—C(326)—H(80)	109.5
C(212)—C(211)—C(213)	110.4 (5)	H(78)—C(326)—C(324)	111.2
C(212)—C(211)—C(214)	110.3 (5)	H(79)—C(326)—H(80)	109.5
C(212)—C(211)—O(211)	103.9 (4)	H(79)—C(326)—C(324)	108.3
C(213)—C(211)—C(214)	112.9 (5)	H(80)—C(326)—C(324)	108.9
C(213)—C(211)—O(211)	109.4 (5)	C(332)—C(331)—C(333)	110.9 (4)
C(214)—C(211)—O(211)	109.5 (5)	C(332)—C(331)—H(82)	108.0
H(31)—C(212)—H(32)	109.5	C(332)—C(331)—N(331)	112.0 (4)
H(31)—C(212)—H(33)	109.5	C(333)—C(331)—H(82)	107.6
H(31)—C(212)—C(211)	109.3	C(333)—C(331)—N(331)	110.5 (4)
H(32)—C(212)—H(33)	109.5	H(82)—C(331)—N(331)	107.7
H(32)—C(212)—C(211)	109.9	O(331)—C(332)—O(341)	124.7 (5)
H(33)—C(212)—C(211)	109.2	O(331)—C(332)—C(331)	124.5 (5)
H(34)—C(213)—H(35)	109.4	O(341)—C(332)—C(331)	110.7 (4)
H(34)—C(213)—H(36)	109.4	H(83)—C(333)—H(84)	109.5
H(34)—C(213)—C(211)	107.4	H(83)—C(333)—H(85)	109.5
H(35)—C(213)—H(36)	109.5	H(83)—C(333)—C(331)	109.6
H(35)—C(213)—C(211)	111.3	H(84)—C(333)—H(85)	109.5
H(36)—C(213)—C(211)	109.6	H(84)—C(333)—C(331)	108.6
H(37)—C(214)—H(38)	109.4	H(85)—C(333)—C(331)	110.2
H(37)—C(214)—H(39)	109.5	C(342)—C(341)—H(86)	109.8
H(37)—C(214)—C(211)	109.0	C(342)—C(341)—H(87)	109.4
H(38)—C(214)—H(39)	109.5	C(342)—C(341)—O(341)	110.1 (5)
H(38)—C(214)—C(211)	110.7	H(86)—C(341)—H(87)	109.4
H(39)—C(214)—C(211)	108.6	H(86)—C(341)—O(341)	109.4
O(211)—C(215)—O(212)	124.9 (4)	H(87)—C(341)—O(341)	108.7
O(211)—C(215)—N(221)	110.0 (4)	H(88)—C(342)—H(89)	109.3
O(212)—C(215)—N(221)	125.0 (4)	H(88)—C(342)—H(90)	109.5
C(222)—C(221)—C(223)	109.7 (4)	H(88)—C(342)—C(341)	109.5
C(222)—C(221)—H(41)	109.2	H(89)—C(342)—H(90)	109.4
C(222)—C(221)—N(221)	111.3 (4)	H(89)—C(342)—C(341)	109.7
C(223)—C(221)—H(41)	108.6	H(90)—C(342)—C(341)	109.2
C(223)—C(221)—N(221)	109.6 (4)
O(111)—C(115)—N(121)—C(121)	−166.6 (4)	H(27)—C(141)—C(142)—H(29)	−179.3
C(115)—N(121)—C(121)—C(122)	−125.0 (4)	H(27)—C(141)—C(142)—H(30)	−58.9
N(121)—C(121)—C(122)—N(131)	129.8 (4)	O(211)—C(211)—C(212)—H(31)	−179.6
C(121)—C(122)—N(131)—C(131)	174.6 (3)	O(211)—C(211)—C(212)—H(32)	−59.4
C(122)—N(131)—C(131)—C(132)	−62.0 (5)	O(211)—C(211)—C(212)—H(33)	60.7
N(131)—C(131)—C(132)—O(141)	154.5 (4)	C(213)—C(211)—C(212)—H(31)	−62.4
C(131)—C(132)—O(141)—C(141)	170.3 (3)	C(213)—C(211)—C(212)—H(32)	57.8
O(211)—C(215)—N(221)—C(221)	173.5 (3)	C(213)—C(211)—C(212)—H(33)	177.9
C(215)—N(221)—C(221)—C(222)	−65.8 (5)	C(214)—C(211)—C(212)—H(31)	63.1
N(221)—C(221)—C(222)—N(231)	154.9 (4)	C(214)—C(211)—C(212)—H(32)	−176.7
C(221)—C(222)—N(231)—C(231)	168.5 (4)	C(214)—C(211)—C(212)—H(33)	−56.6
C(222)—N(231)—C(231)—C(232)	−57.2 (6)	O(211)—C(211)—C(213)—H(34)	−61.4
N(231)—C(231)—C(232)—O(241)	138.4 (5)	O(211)—C(211)—C(213)—H(35)	58.4
C(231)—C(232)—O(241)—C(241)	179.5 (4)	O(211)—C(211)—C(213)—H(36)	179.7
C(315)—N(321)—C(321)—C(322)	−104.8 (4)	C(212)—C(211)—C(213)—H(34)	−175.1
N(321)—C(321)—C(322)—N(331)	142.0 (4)	C(212)—C(211)—C(213)—H(35)	−55.3
C(321)—C(322)—N(331)—C(331)	170.4 (4)	C(212)—C(211)—C(213)—H(36)	66.0
C(322)—N(331)—C(331)—C(332)	−74.8 (5)	C(214)—C(211)—C(213)—H(34)	60.8
N(331)—C(331)—C(332)—O(341)	158.3 (4)	C(214)—C(211)—C(213)—H(35)	−179.3
C(331)—C(332)—O(341)—C(341)	177.8 (4)	C(214)—C(211)—C(213)—H(36)	−58.0
C(115)—O(111)—C(111)—C(112)	66.7 (6)	O(211)—C(211)—C(214)—H(37)	179.7
C(115)—O(111)—C(111)—C(113)	−57.8 (6)	O(211)—C(211)—C(214)—H(38)	−59.8
C(115)—O(111)—C(111)—C(114)	−176.5 (4)	O(211)—C(211)—C(214)—H(39)	60.4
C(111)—O(111)—C(115)—O(112)	−4.3 (7)	C(212)—C(211)—C(214)—H(37)	−66.6
C(111)—O(111)—C(115)—N(121)	176.5 (4)	C(212)—C(211)—C(214)—H(38)	54.0
C(141)—O(141)—C(132)—O(131)	−4.7 (6)	C(212)—C(211)—C(214)—H(39)	174.2
C(132)—O(141)—C(141)—C(142)	−82.5 (6)	C(213)—C(211)—C(214)—H(37)	57.5
C(132)—O(141)—C(141)—H(26)	37.6	C(213)—C(211)—C(214)—H(38)	178.0
C(132)—O(141)—C(141)—H(27)	156.7	C(213)—C(211)—C(214)—H(39)	−61.7
C(215)—O(211)—C(211)—C(212)	175.0 (4)	N(221)—C(221)—C(222)—O(221)	−28.4 (6)
C(215)—O(211)—C(211)—C(213)	57.0 (6)	C(223)—C(221)—C(222)—O(221)	93.1 (5)
C(215)—O(211)—C(211)—C(214)	−67.2 (6)	C(223)—C(221)—C(222)—N(231)	−83.5 (5)
C(211)—O(211)—C(215)—O(212)	4.9 (7)	H(41)—C(221)—C(222)—O(221)	−147.9
C(211)—O(211)—C(215)—N(221)	−177.8 (3)	H(41)—C(221)—C(222)—N(231)	35.4
C(241)—O(241)—C(232)—O(231)	−1.2 (8)	N(221)—C(221)—C(223)—C(224)	−69.2 (5)
C(232)—O(241)—C(241)—C(242)	165.0 (5)	N(221)—C(221)—C(223)—H(42)	52.0
C(232)—O(241)—C(241)—H(56)	−75.9	N(221)—C(221)—C(223)—H(43)	169.9
C(232)—O(241)—C(241)—H(57)	44.5	C(222)—C(221)—C(223)—C(224)	168.2 (4)
C(315)—O(311)—C(311)—C(312)	63.8 (5)	C(222)—C(221)—C(223)—H(42)	−70.5
C(315)—O(311)—C(311)—C(313)	−61.6 (5)	C(222)—C(221)—C(223)—H(43)	47.4
C(315)—O(311)—C(311)—C(314)	−178.9 (4)	H(41)—C(221)—C(223)—C(224)	48.9
C(311)—O(311)—C(315)—O(312)	1.5 (6)	H(41)—C(221)—C(223)—H(42)	170.2
C(311)—O(311)—C(315)—N(321)	−178.0 (3)	H(41)—C(221)—C(223)—H(43)	−71.9
C(341)—O(341)—C(332)—O(331)	1.3 (7)	C(221)—C(223)—C(224)—C(225)	−75.4 (5)
C(332)—O(341)—C(341)—C(342)	−81.4 (6)	C(221)—C(223)—C(224)—C(226)	163.4 (4)
C(332)—O(341)—C(341)—H(86)	39.4	C(221)—C(223)—C(224)—H(44)	44.4
C(332)—O(341)—C(341)—H(87)	158.8	H(42)—C(223)—C(224)—C(225)	163.8
C(121)—N(121)—C(115)—O(112)	14.2 (7)	H(42)—C(223)—C(224)—C(226)	42.6
H(10)—N(121)—C(115)—O(111)	12.4	H(42)—C(223)—C(224)—H(44)	−76.4
H(10)—N(121)—C(115)—O(112)	−166.8	H(43)—C(223)—C(224)—C(225)	45.5
C(115)—N(121)—C(121)—C(123)	112.4 (4)	H(43)—C(223)—C(224)—C(226)	−75.7
C(115)—N(121)—C(121)—H(11)	−5.9	H(43)—C(223)—C(224)—H(44)	165.3
H(10)—N(121)—C(121)—C(122)	56.0	C(223)—C(224)—C(225)—H(45)	179.8
H(10)—N(121)—C(121)—C(123)	−66.5	C(223)—C(224)—C(225)—H(46)	−59.7
H(10)—N(121)—C(121)—H(11)	175.1	C(223)—C(224)—C(225)—H(47)	59.7
C(131)—N(131)—C(122)—O(121)	−2.9 (6)	C(226)—C(224)—C(225)—H(45)	−58.3
H(21)—N(131)—C(122)—O(121)	177.0	C(226)—C(224)—C(225)—H(46)	62.2
H(21)—N(131)—C(122)—C(121)	−5.5	C(226)—C(224)—C(225)—H(47)	−178.4
C(122)—N(131)—C(131)—C(133)	177.7 (4)	H(44)—C(224)—C(225)—H(45)	60.0
C(122)—N(131)—C(131)—H(22)	58.6	H(44)—C(224)—C(225)—H(46)	−179.5
H(21)—N(131)—C(131)—C(132)	118.0	H(44)—C(224)—C(225)—H(47)	−60.1
H(21)—N(131)—C(131)—C(133)	−2.2	C(223)—C(224)—C(226)—H(48)	−179.3
H(21)—N(131)—C(131)—H(22)	−121.3	C(223)—C(224)—C(226)—H(49)	−59.3
C(221)—N(221)—C(215)—O(212)	−9.2 (7)	C(223)—C(224)—C(226)—H(50)	60.8
H(40)—N(221)—C(215)—O(211)	−6.3	C(225)—C(224)—C(226)—H(48)	57.8
H(40)—N(221)—C(215)—O(212)	171.0	C(225)—C(224)—C(226)—H(49)	177.9
C(215)—N(221)—C(221)—C(223)	172.7 (3)	C(225)—C(224)—C(226)—H(50)	−62.1
C(215)—N(221)—C(221)—H(41)	54.3	H(44)—C(224)—C(226)—H(48)	−60.4
H(40)—N(221)—C(221)—C(222)	114.1	H(44)—C(224)—C(226)—H(49)	59.7
H(40)—N(221)—C(221)—C(223)	−7.5	H(44)—C(224)—C(226)—H(50)	179.7
H(40)—N(221)—C(221)—H(41)	−125.9	N(231)—C(231)—C(232)—O(231)	−41.0 (8)
C(231)—N(231)—C(222)—O(221)	−8.2 (7)	C(233)—C(231)—C(232)—O(231)	80.5 (7)
H(51)—N(231)—C(222)—O(221)	172.7	C(233)—C(231)—C(232)—O(241)	−100.1 (5)
H(51)—N(231)—C(222)—C(221)	−10.6	H(52)—C(231)—C(232)—O(231)	−160.7
C(222)—N(231)—C(231)—C(233)	−178.8 (4)	H(52)—C(231)—C(232)—O(241)	18.6
C(222)—N(231)—C(231)—H(52)	62.3	N(231)—C(231)—C(233)—H(53)	60.6
H(51)—N(231)—C(231)—C(232)	121.9	N(231)—C(231)—C(233)—H(54)	−179.6
H(51)—N(231)—C(231)—C(233)	0.3	N(231)—C(231)—C(233)—H(55)	−58.9
H(51)—N(231)—C(231)—H(52)	−118.6	C(232)—C(231)—C(233)—H(53)	−61.2
C(321)—N(321)—C(315)—O(311)	−174.6 (3)	C(232)—C(231)—C(233)—H(54)	58.6
C(321)—N(321)—C(315)—O(312)	5.9 (7)	C(232)—C(231)—C(233)—H(55)	179.2
H(70)—N(321)—C(315)—O(311)	5.9	H(52)—C(231)—C(233)—H(53)	180.0
H(70)—N(321)—C(315)—O(312)	−173.6	H(52)—C(231)—C(233)—H(54)	−60.4
C(315)—N(321)—C(321)—C(323)	135.2 (4)	H(52)—C(231)—C(233)—H(55)	60.3
C(315)—N(321)—C(321)—H(71)	15.2	O(241)—C(241)—C(242)—H(58)	59.8
H(70)—N(321)—C(321)—C(322)	74.7	O(241)—C(241)—C(242)—H(59)	180.0
H(70)—N(321)—C(321)—C(323)	−45.3	O(241)—C(241)—C(242)—H(60)	−60.2
H(70)—N(321)—C(321)—H(71)	−165.3	H(56)—C(241)—C(242)—H(58)	−59.0
C(331)—N(331)—C(322)—O(321)	−6.9 (7)	H(56)—C(241)—C(242)—H(59)	61.3
H(81)—N(331)—C(322)—O(321)	173.5	H(56)—C(241)—C(242)—H(60)	−179.0
H(81)—N(331)—C(322)—C(321)	−9.1	H(57)—C(241)—C(242)—H(58)	179.9
C(322)—N(331)—C(331)—C(333)	161.1 (4)	H(57)—C(241)—C(242)—H(59)	−59.9
C(322)—N(331)—C(331)—H(82)	43.8	H(57)—C(241)—C(242)—H(60)	59.8
H(81)—N(331)—C(331)—C(332)	104.8	O(311)—C(311)—C(312)—H(61)	−179.6
H(81)—N(331)—C(331)—C(333)	−19.3	O(311)—C(311)—C(312)—H(62)	−59.1
H(81)—N(331)—C(331)—H(82)	−136.6	O(311)—C(311)—C(312)—H(63)	60.6
O(111)—C(111)—C(112)—H(1)	179.7	C(313)—C(311)—C(312)—H(61)	−54.4
O(111)—C(111)—C(112)—H(2)	−60.0	C(313)—C(311)—C(312)—H(62)	66.0
O(111)—C(111)—C(112)—H(3)	59.7	C(313)—C(311)—C(312)—H(63)	−174.2
C(113)—C(111)—C(112)—H(1)	−55.9	C(314)—C(311)—C(312)—H(61)	69.2
C(113)—C(111)—C(112)—H(2)	64.1	C(314)—C(311)—C(312)—H(62)	−170.4
C(113)—C(111)—C(112)—H(3)	−176.2	C(314)—C(311)—C(312)—H(63)	−50.6
C(114)—C(111)—C(112)—H(1)	68.0	O(311)—C(311)—C(313)—H(64)	−59.3
C(114)—C(111)—C(112)—H(2)	−172.0	O(311)—C(311)—C(313)—H(65)	60.3
C(114)—C(111)—C(112)—H(3)	−52.3	O(311)—C(311)—C(313)—H(66)	−179.8
O(111)—C(111)—C(113)—H(4)	−59.9	C(312)—C(311)—C(313)—H(64)	176.4
O(111)—C(111)—C(113)—H(5)	60.2	C(312)—C(311)—C(313)—H(65)	−64.0
O(111)—C(111)—C(113)—H(6)	179.8	C(312)—C(311)—C(313)—H(66)	55.8
C(112)—C(111)—C(113)—H(4)	177.2	C(314)—C(311)—C(313)—H(64)	52.4
C(112)—C(111)—C(113)—H(5)	−62.7	C(314)—C(311)—C(313)—H(65)	172.0
C(112)—C(111)—C(113)—H(6)	56.9	C(314)—C(311)—C(313)—H(66)	−68.2
C(114)—C(111)—C(113)—H(4)	53.7	O(311)—C(311)—C(314)—H(67)	59.7
C(114)—C(111)—C(113)—H(5)	173.9	O(311)—C(311)—C(314)—H(68)	−179.8
C(114)—C(111)—C(113)—H(6)	−66.5	O(311)—C(311)—C(314)—H(69)	−60.6
O(111)—C(111)—C(114)—H(7)	60.4	C(312)—C(311)—C(314)—H(67)	176.6
O(111)—C(111)—C(114)—H(8)	179.8	C(312)—C(311)—C(314)—H(68)	−62.9
O(111)—C(111)—C(114)—H(9)	−59.9	C(312)—C(311)—C(314)—H(69)	56.3
C(112)—C(111)—C(114)—H(7)	176.6	C(313)—C(311)—C(314)—H(67)	−58.7
C(112)—C(111)—C(114)—H(8)	−64.1	C(313)—C(311)—C(314)—H(68)	61.9
C(112)—C(111)—C(114)—H(9)	56.3	C(313)—C(311)—C(314)—H(69)	−178.9
C(113)—C(111)—C(114)—H(7)	−58.6	N(321)—C(321)—C(322)—O(321)	−40.6 (6)
C(113)—C(111)—C(114)—H(8)	60.7	C(323)—C(321)—C(322)—O(321)	80.4 (5)
C(113)—C(111)—C(114)—H(9)	−179.0	C(323)—C(321)—C(322)—N(331)	−96.9 (4)
N(121)—C(121)—C(122)—O(121)	−52.7 (6)	H(71)—C(321)—C(322)—O(321)	−160.5
C(123)—C(121)—C(122)—O(121)	68.9 (5)	H(71)—C(321)—C(322)—N(331)	22.1
C(123)—C(121)—C(122)—N(131)	−108.6 (4)	N(321)—C(321)—C(323)—C(324)	−59.9 (5)
H(11)—C(121)—C(122)—O(121)	−171.6	N(321)—C(321)—C(323)—H(72)	62.5
H(11)—C(121)—C(122)—N(131)	10.9	N(321)—C(321)—C(323)—H(73)	−178.8
N(121)—C(121)—C(123)—C(124)	173.0 (4)	C(322)—C(321)—C(323)—C(324)	178.7 (4)
N(121)—C(121)—C(123)—H(12)	−66.0	C(322)—C(321)—C(323)—H(72)	−58.9
N(121)—C(121)—C(123)—H(13)	51.8	C(322)—C(321)—C(323)—H(73)	59.8
C(122)—C(121)—C(123)—C(124)	50.4 (5)	H(71)—C(321)—C(323)—C(324)	59.8
C(122)—C(121)—C(123)—H(12)	171.3	H(71)—C(321)—C(323)—H(72)	−177.8
C(122)—C(121)—C(123)—H(13)	−70.8	H(71)—C(321)—C(323)—H(73)	−59.1
H(11)—C(121)—C(123)—C(124)	−68.9	C(321)—C(323)—C(324)—C(325)	−67.3 (6)
H(11)—C(121)—C(123)—H(12)	52.0	C(321)—C(323)—C(324)—C(326)	168.1 (4)
H(11)—C(121)—C(123)—H(13)	169.9	C(321)—C(323)—C(324)—H(74)	52.1
C(121)—C(123)—C(124)—C(125)	−173.3 (4)	H(72)—C(323)—C(324)—C(325)	170.7
C(121)—C(123)—C(124)—C(126)	62.6 (6)	H(72)—C(323)—C(324)—C(326)	46.1
C(121)—C(123)—C(124)—H(14)	−56.2	H(72)—C(323)—C(324)—H(74)	−69.9
H(12)—C(123)—C(124)—C(125)	65.4	H(73)—C(323)—C(324)—C(325)	52.4
H(12)—C(123)—C(124)—C(126)	−58.7	H(73)—C(323)—C(324)—C(326)	−72.2
H(12)—C(123)—C(124)—H(14)	−177.5	H(73)—C(323)—C(324)—H(74)	171.8
H(13)—C(123)—C(124)—C(125)	−52.0	C(323)—C(324)—C(325)—H(75)	−61.4
H(13)—C(123)—C(124)—C(126)	−176.2	C(323)—C(324)—C(325)—H(76)	58.5
H(13)—C(123)—C(124)—H(14)	65.0	C(323)—C(324)—C(325)—H(77)	178.2
C(123)—C(124)—C(125)—H(15)	56.7	C(326)—C(324)—C(325)—H(75)	61.6
C(123)—C(124)—C(125)—H(16)	176.9	C(326)—C(324)—C(325)—H(76)	−178.5
C(123)—C(124)—C(125)—H(17)	−63.3	C(326)—C(324)—C(325)—H(77)	−58.8
C(126)—C(124)—C(125)—H(15)	−178.3	H(74)—C(324)—C(325)—H(75)	−179.7
C(126)—C(124)—C(125)—H(16)	−58.1	H(74)—C(324)—C(325)—H(76)	−59.8
C(126)—C(124)—C(125)—H(17)	61.7	H(74)—C(324)—C(325)—H(77)	60.0
H(14)—C(124)—C(125)—H(15)	−60.2	C(323)—C(324)—C(326)—H(78)	−56.5
H(14)—C(124)—C(125)—H(16)	60.0	C(323)—C(324)—C(326)—H(79)	63.9
H(14)—C(124)—C(125)—H(17)	179.7	C(323)—C(324)—C(326)—H(80)	−177.2
C(123)—C(124)—C(126)—H(18)	61.0	C(325)—C(324)—C(326)—H(78)	178.9
C(123)—C(124)—C(126)—H(19)	−179.1	C(325)—C(324)—C(326)—H(79)	−60.8
C(123)—C(124)—C(126)—H(20)	−58.8	C(325)—C(324)—C(326)—H(80)	58.2
C(125)—C(124)—C(126)—H(18)	−61.9	H(74)—C(324)—C(326)—H(78)	59.3
C(125)—C(124)—C(126)—H(19)	57.9	H(74)—C(324)—C(326)—H(79)	179.6
C(125)—C(124)—C(126)—H(20)	178.3	H(74)—C(324)—C(326)—H(80)	−61.4
H(14)—C(124)—C(126)—H(18)	179.8	N(331)—C(331)—C(332)—O(331)	−25.2 (7)
H(14)—C(124)—C(126)—H(19)	−60.3	C(333)—C(331)—C(332)—O(331)	98.7 (6)
H(14)—C(124)—C(126)—H(20)	60.1	C(333)—C(331)—C(332)—O(341)	−77.8 (5)
N(131)—C(131)—C(132)—O(131)	−30.5 (7)	H(82)—C(331)—C(332)—O(331)	−143.7
C(133)—C(131)—C(132)—O(131)	89.9 (6)	H(82)—C(331)—C(332)—O(341)	39.8
C(133)—C(131)—C(132)—O(141)	−85.1 (4)	N(331)—C(331)—C(333)—H(83)	−57.1
H(22)—C(131)—C(132)—O(131)	−151.5	N(331)—C(331)—C(333)—H(84)	62.5
H(22)—C(131)—C(132)—O(141)	33.5	N(331)—C(331)—C(333)—H(85)	−177.6
N(131)—C(131)—C(133)—H(23)	−59.3	C(332)—C(331)—C(333)—H(83)	178.2
N(131)—C(131)—C(133)—H(24)	60.7	C(332)—C(331)—C(333)—H(84)	−62.3
N(131)—C(131)—C(133)—H(25)	−179.4	C(332)—C(331)—C(333)—H(85)	57.6
C(132)—C(131)—C(133)—H(23)	178.6	H(82)—C(331)—C(333)—H(83)	60.3
C(132)—C(131)—C(133)—H(24)	−61.4	H(82)—C(331)—C(333)—H(84)	179.9
C(132)—C(131)—C(133)—H(25)	58.4	H(82)—C(331)—C(333)—H(85)	−60.2
H(22)—C(131)—C(133)—H(23)	60.2	O(341)—C(341)—C(342)—H(88)	−179.9
H(22)—C(131)—C(133)—H(24)	−179.8	O(341)—C(341)—C(342)—H(89)	−59.9
H(22)—C(131)—C(133)—H(25)	−60.0	O(341)—C(341)—C(342)—H(90)	60.1
O(141)—C(141)—C(142)—H(28)	−59.3	H(86)—C(341)—C(342)—H(88)	59.7
O(141)—C(141)—C(142)—H(29)	60.1	H(86)—C(341)—C(342)—H(89)	179.7
O(141)—C(141)—C(142)—H(30)	−179.4	H(86)—C(341)—C(342)—H(90)	−60.3
H(26)—C(141)—C(142)—H(28)	−179.6	H(87)—C(341)—C(342)—H(88)	−60.5
H(26)—C(141)—C(142)—H(29)	−60.1	H(87)—C(341)—C(342)—H(89)	59.5
H(26)—C(141)—C(142)—H(30)	60.1	H(87)—C(341)—C(342)—H(90)	179.6
H(27)—C(141)—C(142)—H(28)	61.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N121—H10···O221	0.95	2.25	2.948 (5)	129
N131—H21···O321^i	0.95	2.06	2.983 (5)	164
N221—H40···O121	0.95	2.08	2.925 (4)	148
N231—H51···O312	0.95	1.91	2.850 (5)	173
N321—H70···O112^ii	0.95	1.96	2.865 (5)	158
N331—H81···O212	0.95	2.08	2.945 (5)	151

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) −x+1/2, −y+1, z+1/2.